Azo dyes having 2,6-diaminopyridine derivatives as coupling components

Abstract

Azo dyes having 2,6-diaminopyridine derivatives as coupling components which preferably bear cyano or carbamoyl as substituents in the 3-position. The dyes give brilliant yellow to blue colorations, particularly on synthetic polyesters, which are distinguished by outstanding fastness properties.

Description

The invention relates to dyes of the formula (I): ##STR1## in which D is the radical of a diazo component;

R is unsubstituted or substituted alkyl or unsubstituted or substituted phenyl; X is hydrogen, cyano or unsubstituted or substituted carbamoyl; R.sup.1 is a radical of the formula: C.sub.6 H.sub.5 ; ##STR2## (CH.sub.2).sub.3 OCH.sub.2 CH.sub.2 OH (CH.sub.2).sub.3 O(CH.sub.2).sub.6 OH, ##STR3## (CH.sub.2).sub.3 OC.sub.2 H.sub.4 OR.sup.7, (CH.sub.2).sub.3 (OC.sub.2 H.sub.4).sub.q OR.sup.8, (CH.sub.2).sub.3 OR.sup.9, ##STR4## or the radical containing hydroxyl groups of the formula: ##STR5## R.sup.2 is hydrogen, R.sup.1 or an unsubstituted or substituted aliphatic, cycloaliphatic, araliphatic or aryl radical; R.sup.3 is alkyl of one to three carbon atoms or hydroxyalkyl; R.sup.4 is hydrogen, alkyl of one to three carbon atoms or hydroxyalkyl; R.sup.5 is hydrogen or hydroxy; R.sup.6 is hydrogen, alkyl of one to four carbon atoms, methoxy, ethoxy or chloro; R.sup.7 is ethyl, propyl, butyl, cyclohexyl, benzyl, phenylethyl or methylphenyl; R.sup.8 is hydrogen, alkyl of one to four carbon atoms, cyclohexyl, phenyl, methylphenyl, benzyl or phenylethyl; R.sup.9 is cyclohexyl, phenyl, methylphenyl, benzyl or phenylethyl; m is 1 or 2; n is zero, 1 or 2; q is 2, 3 or 4; and p is 1, 2, 3 or 4.

The radicals (D) of the diazo components may be derived for example from amines of the benzene, naphthalene, diphenyl, benzothiazole, benzoisothiazole, thiazole, thiadiazole, thiophene, triazole, benzotriazole, indazole, pyrazole, azobenzene or anthraquinone series.

The following are examples of substituents for the radical (D) of the diazo components: in the benzene series: chloro, bromo, nitro, cyano, trifluoromethyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl, p-(.beta.-hydroxyethyl)-phenylsulfonyl, carbomethoxy, carboethoxy, carbobutoxy, carbo-.beta.-methoxyethoxy, carbo-.beta.-ethylhexoxy, carbo-.beta.-hydroxyethoxy, carbamoyl, N-substituted carbamoyl, N-disubstituted carbamoyl, N-substituted sulfamoyl, N-disubstituted sulfamoyl, methyl, ethyl, methoxy and ethoxy;

Examples of N-substituents of carbamoyl or sulfamoyl are methyl, ethyl, propyl, butyl, .beta.-ethylhexyl, cyclohexyl, benzyl, phenylethyl, .beta.-hydroxyethyl, .beta.-hydroxypropyl, .beta.-methoxyethyl, .gamma.-methoxypropyl, .gamma.-ethoxypropyl, pyrrolidide, piperidide and morpholide.

In the azobenzene series; chloro, bromo, nitro, cyano, carbomethoxy, carboethoxy, methyl, ethyl, methoxy, ethoxy, hydroxy, acetylamino, formyl, .beta.-hydroxyethoxy and ethoxycarbonylamino.

In the heterocyclic series; chloro, bromo, nitro, cyano, methyl, ethyl, phenyl, methoxy, ethoxy, methylmercapto, .beta.-carbomethoxyethylmercapto, .beta.-carboethoxyethylmercapto, carbomethoxy, carboethoxy, acetyl, methylsulfonyl and ethylsulfonyl.

The radical D may be derived for example from the following amines: aniline, o-toluidine, m-toluidine, p-toluidine, o-nitroaniline, m-nitroaniline, p-nitroaniline, o-cyanoaniline, m-cyanoaniline, p-cyanoaniline, 2,4-dicyanoaniline, o-chloroaniline, m-chloroaniline, p-chloroaniline, 3,4-dichloroaniline, 2,5-dichloroaniline, 2,4,5-trichloroaniline, 2,4,6-trichloroaniline, o-bromoaniline, m-bromoaniline, p-bromoaniline, 2,4,6-tribromoaniline, 2-chloro-4-nitroaniline, 2-bromo-4-nitroaniline, 2-cyano-4-nitroaniline, 2-methylsulfonyl-4-nitroaniline, 2-methyl-4-nitroaniline, 2-methoxy-4-nitroaniline, 4-chloro-2-nitroaniline, 4-methyl-2-nitroaniline, 4-methoxy-2-nitroaniline, 1-amino-2-trifluoromethyl-4-chlorobenzene, 2-chloro-5-aminobenzonitrile, 2-amino-5-chlorobenzonitrile, 1-amino-2-nitrobenzene-4-sulfonic acid n-butylamide, 1-amino-2-nitrobenzene-4-sulfonic acid .beta.-methoxyethylamide, 2,4-dinitroaniline, 2,4-dinitro-6-chloroaniline, 2,4-dinitro-6-bromoaniline, 2,4-dinitro-6-cyanoaniline, 1-amino-2,4-dinitrobenzene-6-methylsulfone, 2,6-dichloro-4-nitroaniline, 2,6-dibromo-4-nitroaniline, 2-chloro-6-bromo-4-nitroaniline, 2,6-dicyano-4-nitroaniline, 2-cyano-4-nitro-6-chloroaniline, 2-cyano-4-nitro-6-bromoaniline, 1-aminobenzene-4-methylsulfone, 1-amino-2,6-dibromobenzene-4 -methylsulfone, 1-amino-2,6-dichlorobenzene-4-methylsulfone, 1-amino-2,6-dinitrobenzene-6-carboxylic methyl ester or .beta.-methoxyethyl ester, propyl 3,5-dichloroanthranilate, .beta.-methoxyethyl 3,5-dibromoanthranilate, N-benzoyl-p-phenylenediamine, N-acetyl-p-phenylenediamine, N-phenylsulfonyl-p-phenylenediamine, N-phenylsulfonyl-m-phenylenediamine, 4-aminoacetophenone, 4-aminobenzophenone, 2-aminobenzophenone, 2-aminodiphenylsulfone, methyl 2-aminobenzoate, methyl 3-aminobenzoate, methyl 4-aminobenzoate and the corresponding ethyl, propyl, butyl, isobutyl, .beta.-ethylhexyl, cyclohexyl, benzyl, phenyl, .beta.-methoxyethyl, .beta.-ethoxyethyl, .beta.-butoxyethyl, methyl diglycol, ethyl diglycol, methyl triglycol, ethyl triglycol, .beta.-hydroxyethyl, .beta.-acetoxyethyl, .beta.-(.beta.'-hydroxyethoxy)-ethyl, .beta.-hydroxypropyl, .gamma.-hydroxypropyl, .omega.-hydroxybutyl, .omega.-hydroxyhexyl esters, methyl 5-nitroanthranilate and the corresponding isobutyl, methyl diglycol, .beta.-methoxyethyl, .beta.-butoxyethyl and .beta.-acetoxyethyl esters of 5-nitroanthranilic acid, the dimethyl, diethyl, dipropyl or dibutyl ester of 3-aminophthalic acid, 4-aminophthalic acid, 5-aminoisophthalic acid or aminoterephthalic acid, the amide, methylamide, propylamide, butylamide, isobutylamide, cyclohexylamide, 62 -ethylhexylamide, .gamma.-methoxypropylamide, .alpha.-ethoxypropuylamide or anilide of 3-aminobenzoic acid or 4-aminobenzoic acid, the dimethylamide, diethylamide, pyrrolidide, morpholide or N-methyl-N-.beta.-hydroxyethylamide of 2-aminobenzoic acid, 3-aminobenzoic acid or 4-aminobenzoic acid, the diamide or bis-.gamma.-methoxypropylamide of 5-aminoisophthalic acid, the bisdiethylamide of aminoterephthalic acid, the imide, .beta.-hydroxyethylimide, .gamma.-hydroxypropylimide, phenylimide or p-tolylimide of 3-aminophthalic acid or 4-aminophthalic acid, the .beta.-hydroxyethylimide of 3-amino-6-nitrophthalic acid, the dimethylamide, diethylamide, pyrrolidide, morpholide or N-methylanilide of 2-aminobenzenesulfonic acid, 3-aminobenzenesulfonic acid or 4-aminobenzenesulfonic acid, 2'-aminophenyl methylsulfonate, 3'-aminophenyl methylsulfonate, 4'-aminophenyl methylsulfonate, 2'-aminophenyl ethylsulfonate, 3'-aminophenyl ethylsulfonate, 4'-aminophenyl ethylsulfonate, 2'-aminophenyl butylsulfonate, 3'-aminophenyl butylsulfonate, 4'-aminophenyl butylsulfonate, 2'-aminophenyl benzenesulfonate, 3'-aminophenyl benzenesulfonate, 4'-aminophenyl benzenesulfonate, the ethylimide, butylimide, .beta.-methoxyethylimide or .gamma.-methoxypropylimide of 4-aminonaphthalic acid, 1-aminonaphthalene, 2-aminonaphthalene, 1-amino-2-ethoxynaphthalene, 2-aminodiphenyl, 4-aminodiphenyl, 1-aminoanthraquinone, 1-amino-4-chloroanthraquinon, 3-aminodiphenylene oxide, 4-aminodiphenylene oxide, 2-aminobenzothiazole, 2-amino-6-methylsulfonylbenzothiazole, 2-amino-6-nitrobenzothiazole, 5,6-dichloro-2-aminobenzothiazole, 6,7-dichloro-2-aminobenzothiazole, 4-amino-5-bromo-7-nitrol-1,2-benzoisothiazole, 3-amino-5-nitro-2,1-benzoisothiazole, 3-amino-5-nitro-7-bromo-2,1-benzoisothiazole, 2-aminothiazole, 2-amino-5-nitrothiazole, 2-amino-b 4-methylthiazole-5-carboxylic ethyl ester, 2-amino-4-methyl-5-acetylthiazole, 2-amino-3-cyano-4-methylthiophene-5-carboxylic esters, 2-phenyl-5-amino-1,3,4-thiadiazole, 3-methylmercapto-5-amino-1,2,4-thiadiazole, 3-.beta.-carbomethoxyethylmercapto-5-amino-1,2,4-thiadiazole, 3-amino-1,2,4-triazole, 4-amino-7-nitrobenzotriazole, 3-aminoindazole, 3-amino-5-chloroindazole, 3-amino-5-nitroindazole, 1-benzyl-5-aminopyrazole and 1-phenyl-5-aminopyrazole.

Examples of suitable diazo components of the aminoazo series are: 2',4-dimethyl-4-aminoazobenzene, 3',2-dimethyl-4-aminoazobenzene, 2,5-dimethyl-4-aminoazobenzene, 2-methyl-5-methoxy-4-aminoazobenzene, 2-methyl-4',5-dimethoxy-4-aminoazobenzene, 4'-chloro-2-methyl-5-methoxy-4-aminoazobenzene, 4'-nitro-2-methyl-5-methoxy-4-aminoazobenzene, 4'-hydroxy-2-methyl-5-methoxy-4-aminoazobenzene, 4'-(.beta.-hydroxyethoxy)-2-methyl-5-methoxy-4-aminoazobenzene, 4'-hydroxy-2,2'-dimethyl-5-methoxy-4-aminoazobenzene, 4'-hydroxy-4-aminoazobenzene, 4'-hydroxy-2'-methyl-4-aminoazobenzene, 4'-hydroxy-3'-methyl-4-aminoazobenzene, 2'-hydroxy-5'-methyl-4-aminoazobenzene, 4'-hydroxy-2-methoxy-4-aminoazobenzene, 4'-hydroxy-2'-chloro-4-aminoazobenzene, 4'-hydroxy-2,5-dimethoxy-4-aminoazobenzene, 4'-hydroxy-2,6-dichloro-4-aminoazobenzene, 4-hydroxy-3-methoxy-4-aminoazobenzene, 4'-chloro-2-methyl-4-aminoazobenzene, 4'-formyl-2-methyl-4-aminoazobenzene, 4'-(ethoxycarbonylamino)-2-methyl-4-aminoazobenzene, 2,5-dimethoxy-4-aminoazobenzene, 4' -chloro-2,5-dimethoxy-4-aminoazobenzene, 4'-nitro-2,5-dimethoxy-4-aminoazobenzene, 4'-(hydroxyethoxy)-2,5-dimethoxy-4-aminoazobenzene, 4'-chloro-2,5-dimethyl-4-aminoazobenzene, 4'-methoxy-2,5-dimethyl-4-aminoazobenzene, 4'-nitro-4-aminoazobenzene, 3,5-dibromo-4-aminoazobenzene, 2,3'-dichloro-4-aminoazobenzene, 3-methoxy-4-aminoazobenzene, 1-phenylazo-4-aminonaphthalene and 2-phenylazo-3-ethoxy-4-aminonaphthalene.

Examples of radicals R are ethyl, n-propyl, isopropyl, butyl, pentyl, .alpha.-ethylpentyl, phenyl, methylphenyl and preferably methyl.

Examples of substituted carbamoyl radicals for X are N-methylcarbamoyl, N-ethylcarbamoyl, N-butylcarbamoyl, N-.beta.-hydroxyethylcarbamoyl, N-.gamma.-methoxypropylacarbamoyl, N,N-dimethylcarbamoyl, N,N-diethylcarbamoyl, N,N-dibutylcarbamoyl or N-methyl-N-.beta.-hydroxyethylcarbamoyl. Unsubstituted carbamoyl is preferred because of its easier accessibility.

Examples of individual radicals R.sup.1, in addition to those already specified, are: (CH.sub.2).sub.3 OC.sub.2 H.sub.4 OC.sub.2 H.sub.5, (CH.sub.2).sub.3 OC.sub.2 H.sub.4 --OCH(CH.sub.3).sub.2, (CH.sub.2).sub.3 OC.sub.2 H.sub.4 OC.sub.4 H.sub.9, (CH.sub.2).sub.3 OC.sub.2 H.sub.4 OCH.sub.2 C.sub.6 H.sub.5, (CH.sub.2).sub.3 OC.sub.2 H.sub.4 OC.sub.2 H.sub.4 C.sub.6 H.sub.5, ##STR6## (CH.sub.2).sub.3 (OC.sub.2 H.sub.4).sub.2 OCH.sub.3, ##STR7## and the corresponding radicals in which the grouping --OC.sub.2 H.sub.4 --, ##STR8## is present twice, thrice or four times, and compounds in which C.sub.6 H.sub.5 has been replaced by C.sub.6 H.sub.4 CH.sub.3.

Other examples are: (CH.sub.2).sub.3 OC.sub.6 H.sub.5, (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5, (CH.sub.2).sub.3 OC.sub.2 H.sub.4 C.sub.6 H.sub.5, ##STR9## and the radicals having C.sub.6 H.sub.4 CH.sub.3 instead of C.sub.6 H.sub.5.

Radicals R.sup.2 (in addition to being hydrogen or R.sup.1) may for example be alkyl of one to eight carbon atoms which may be interrupted by oxygen atoms and may bear hydroxy, alkoxy, acyloxy, carboxy, carboxylic ester, cycloalkoxy, aralkoxy or aroxy as substituents, cycloalkyl of five to eight carbon atoms which may bear hydroxy, chloro, hydroxyalkyl, chloroalkyl or alkyl as substituents, aralkyl of seven to fifteen carbon atoms, phenyl which may bear chloro, hydroxy, alkoxy, alkyl, hydroxyalkyl or hydroxyalkoxy as substituents, and also alkenyl, pyrrolidonyalkyl and carboxyalkyl.

Examples of radicals R.sup.2 are: unsubstituted or substituted alkyl radicals: CH.sub.3, C.sub.2 H.sub.5, n- and i-C.sub.3 H.sub.7, n- and i-C.sub.4 H.sub.9, C.sub.6 H.sub.13, ##STR10## CH.sub.2 CH=CH.sub.2, CH.sub.2 CH.sub.2 OH, (CH.sub.2).sub.3 OH, (CH.sub.2).sub.4 OH, (CH.sub.2).sub.6 OH, (CH.sub.2).sub.2 O(CH.sub.2).sub.2 OH, (CH.sub.2).sub.3 O(CH.sub.2).sub.4 OH, ##STR11## (CH.sub.2).sub.3 OC.sub.2 H.sub.4 OCH.sub.3, (CH.sub.2).sub.3 OC.sub.2 H.sub.4 OC.sub.6 H.sub.5, CH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5, CH.sub.2 Ch.sub.2 OC.sub.3 H.sub.7, CH.sub.2 CH.sub.2 OC.sub.4 H.sub.9, (CH.sub.2).sub.3 OCH.sub.3, (CH.sub.2).sub.3 OC.sub.2 H.sub.5, (CH.sub.2).sub.3 OC.sub.3 H.sub.7, (CH.sub.2).sub.3 OC.sub.4 H.sub.9, (CH.sub.2).sub.3 OC.sub.6 H.sub.13, (CH.sub.2).sub.3 OC.sub.8 H.sub.17, ##STR12## carboxyalkyl and carbalkoxyalkyl radicals of the formulae: CH.sub.2 --COOE, CH.sub.2 --CH.sub.2 --COOE, (CH.sub.2).sub.5 --COOE or (CH.sub.2).sub.2 --O--CO--(CH.sub.2).sub.2 --COOE where E may be for example hydrogen, methyl, ethyl, propyl, benzyl, .beta.-hydroxyethyl, .omega.-hydroxyhexyl, .delta.-hydroxybutyl, .beta.-methoxyethyl, .gamma.-methoxypropyl, .gamma.-ethoxypropyl, .beta.-phenoxyethyl or .beta.-hydroxyethoxyethyl; acyloxyalkyl radicals of the formulae: CH.sub.2 --CH.sub.2 --O--acyl, (CH.sub.2).sub.3 --O--acyl, ##STR13## (CH.sub.2).sub.6 --O--acyl, (CH.sub.2).sub.2 --O--(CH.sub.2).sub.2 --O--acyl or (CH.sub.2).sub.3 --O--(CH.sub.2).sub.4 --O--acyl in which acyl is for example CO--H, CO--CH.sub.3, CO--C.sub.2 H.sub.5, ##STR14## CO--CH.sub.2 Cl, CO--CH.sub.2 --CO--CH.sub.3, CO--CH=CH.sub.2, ##STR15## CO--CH=CH--COOH, CO--(CH.sub.2).sub.2 --COOH, CO--(CH.sub.2).sub.2 --COOC.sub.2 H.sub.5, ##STR16## and the radicals R.sup.1 containing a hydroxyl group may similarly be esterified with acyl.

Acyl radicals also include COOV and CONHB in which B may be for example alkyl or aryl. Examples are COOCH.sub.3, COOC.sub.2 H.sub.5, COOC.sub.4 H.sub.9, CONCH.sub.3, CONHC.sub.4 H.sub.9, CONHC.sub.6 H.sub.5, CONHC.sub.6 H.sub.4 Cl and CONH-C.sub.6 H.sub.3 Cl.sub.2 ; pyrrolidonylalkyl radicals of the formulae: ##STR17## cycloalkyl radicals of the formulae: ##STR18## aralkyl radicals of the formulae: CH.sub.2 --C.sub.6 H.sub.5, C.sub.2 H.sub.4 --C.sub.6 H.sub.5, ##STR19## and with C.sub.6 H.sub.4 --CH.sub.3 instead of C.sub.6 H.sub.5 and the radicals of the formulae:

C.sub.6 h.sub.4 cl, C.sub.6 H.sub.3 Cl.sub.2, C.sub.6 Cl.sub.4 CH.sub.3, C.sub.6 H.sub.3 (CH.sub.3).sub.2, C.sub.6 H.sub.4 CN, C.sub.6 H.sub.4 OH, C.sub.6 H.sub.4 OCH.sub.2 CH.sub.2 OH, C.sub.6 H.sub.4 OCH.sub.3, C.sub.6 H.sub.4 OC.sub.2 H.sub.5 and C.sub.6 H.sub.4 NHCOCH.sub.3.

Dyes of the formula (I) may be produced by reacting a diazo compound of an amine of the formula (II):

d--nh.sub.2 (ii) with a coupling component of the formula (III): ##STR20## in which D, R, X, R.sup.1 and R.sup.2 have the meanings given above.

Diazotization of the amines is carried out conventionally. Coupling is also carried out conventionally in aqueous medium with or without the addition of solvents at a weakly to strongly acid pH.

Production of the coupling components of the formula (III) is described in principle in German Patent Specification No. 2,062,717 and the statements therein may be applied in the present case.

If the dye of formula (I) of the invention contains an ester group in the radical R.sup.1 and/or R.sup.2 the compounds of formula (I) may in principle be prepared by the said process if the appropriate ester group is already contained in the coupling component. In some cases however it is convenient to introduce the acid radical (acyl) into the finished dye of formula (I). The free acids, their anhydrides, chlorides or esters are suitable for this and conveniently an inert diluent or solvent is added such as monochlorobenzene, dichlorobenzene or trichlorobenzene, tetrahydrofuran, dioxane, dimethylformamide, N-methylpyrrolidone or pyridine.

In esterification with the free acid it may be advantageous to add an inorganic or organic catalyst, for example hydrogen chloride gas or p-toluenesulfonic acid and to allow the water formed to escape by evaporation from the reaction mixture. When an acid anhydride or chloride is used for esterification, the acid itself may in special cases be used as the solvent. Thus reaction with acetic anhydride may be carried out in glacial acetic acid. When using an acid chloride as the esterifying agent it is advantageous to add an acid-binding agent, for example sodium carbonate, sodium acetate, magnesium oxide or pyridine to the reaction mixture. The following are specific examples of esterifying agents: formic acid, acetic acid, chloroacetic acid and the esters, anhydrides and chlorides of these acids, also chloroformates, diketene or isocyanates. Conversion of the carboxyl group into the carboxylic ester group may similarly be carried out in the finished dye by conventional methods known from the literature.

Particular industrial value attaches to dyes and mixtures of dyes of the formula (Ia): ##STR21## in which Y is nitro, cyano, chloro, bromo, carbomethoxy, carboethoxy, .beta.-methoxycarboethoxy, methylsulfonyl, ethylsulfonyl, methyl, methoxy or phenylazo;

Y.sup.1 is hydrogen, nitro, chloro, bromo, cyano, methyl, methoxy, carbomethoxy, carboethoxy, methylsulfonyl or ethylsulfonyl; Y.sup.2 is hydrogen, chloro, bromo, cyano, methyl, methoxy, carbomethoxy or carboxethoxy; one A.sup.1 may be a radical of the formula R.sup.1 and the other A.sup.1 may be hydrogen or a radical containing a hydroxyl or alkoxy group and the hydroxyl group may be esterified by formyl or acetyl.

Preferred radicals R.sup.1 are for example: C.sub.6 H.sub.5, ##STR22## (CH.sub.2).sub.3 --OC.sub.2 H.sub.4 OH, (CH.sub.2).sub.3 O(CH.sub.2).sub.6 OH, ##STR23## (CH.sub.2).sub.3 OC.sub.2 H.sub.4 OC.sub.6 H.sub.5, ##STR24## (CH.sub.2).sub.3 OC.sub.2 H.sub.4 OCH.sub.2 C.sub.6 H.sub.5, (CH.sub.2).sub.3 (OC.sub.2 H.sub.4).sub.2 OR.sup.8, ##STR25## (CH.sub.2).sub.3 OC.sub.6 H.sub.5, (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5 and (CH.sub.2).sub.3 OC.sub.2 H.sub.4 C.sub.6 H.sub.5, R.sub.8 having the meanings given above.

Examples of other preferred radicals A.sup.1 are hydrogen, .omega.-hydroxybutyl, .omega.-hydroxyhexyl, .beta.-hydroxyethyl, .beta.-hydroxypropyl and radicals of the formulae:

C.sub.2 h.sub.4 och.sub.3, c.sub.3 h.sub.6 och.sub.3, ch.sub.2 ch.sub.2 ocho, ch.sub.2 ch.sub.2 ch.sub.2 ocho, ch.sub.2 --ch.sub.2 --ococh.sub.3, (ch.sub.2).sub.3 o(ch.sub.2).sub.4 oh, (ch.sub.2).sub.2 o(ch.sub.2).sub.2 oh, ##STR26## (ch.sub.2).sub.3 or.sup.10, (ch.sub.2).sub.3 oc.sub.2 h.sub.4 och.sub.3 and (CH.sub.2).sub.3 OC.sub.2 H.sub.4 OC.sub.6 H.sub.5, R.sup.10 being hydrogen or alkyl of one to four carbon atoms. Preferred examples of acyl radicals are CHO, COCH.sub.3 and COC.sub.2 H.sub.5. Moreover the following are preferred: ##STR27## Another group of preferred dyes has the formula: ##STR28## in which D, R.sup.1 and X have the meanings given above.

The radicals R.sup.1 and R.sup.2 are advantageously chosen so that they contain at least one hydrogen atom or one or more oxygen atoms and the total number of carbon atoms is in the range from five to twenty, preferably from five to sixteen.

Those dyes are also particularly valuable which contain as dizao components benzothiazole, benzoisothiazole, thiazole, thidadiazole or thiophene which may bear nitro, chloro, bromo, cyano, methyl, methylmercapto, .beta.-carbomethoxyethylmercapto, .beta.-carboethoxyethylmercapto, carbomethoxy, carboethoxy, carboglycol ester or acetyl as substituents.

The following examples are given from among the particularly preferred diazo components: 4-nitroaniline, 2-chloro-4-nitroaniline, 2-bromo-4-nitroaniline, 2-cyano-4-nitronailine, 2-methoxy-4-nitroaniline, 2-amino-5-nitrophenylsulfonic acid dimethylamide, 2-amino-5-nitrophenylsulfonic acid butylamide, 2-amino-5-nitrophenylsulfonic acid .beta.-methoxyethylamide, 2-aminobenzonitrile, 3-chloro-4-aminobenzonitrile, 2-chloro-5-aminobenzonitrile, 2-amino-5-chlorobenzonitrile, 2,5-dichloro-4-aminobenzonitrile, 1-amino-2,4-dicyanobenzene, 1-amino-2,4-dicyano-6-chlorobenzene, 2-chloro-4-amino-5-nitrobenzonitrile, 2-amino-3-chloro-5-nitrobenzonitrile, 1-amino-3-bromo-5-nitrobenzonitrile, 2,6-dicyano-4-nitroaniline, 2,5-dichloro-4-nitroaniline, 2,6-dichloro-4-nitroaniline, 2,6-dibromo-4-nitroaniline, 2-chloro-6-bromo-4-nitroaniline, 2,4-dinitroaniline, 2,4-dinitro-6-chloroaniline, 2,4-dinitro-6-bromoaniline, 2-amino-3,5-dinitrobenzonitrile, 1-amino-4-nitrobenzene-2-methylsulfone, 1-amino-4-nitrobenzene-2-ethylsulfone, 4-methylsulfonylaniline, 1-amino-2-chlorobenzene-4-methylsulfone, 1-amino-2,6-dibromobenzene-4-methylsulfone, 1-amino-2,6-dichlorobenzene-4-methylsulfone, 2-aminobenzoic acid esters, 4-aminobenzoic acid esters, 2-amino-5-nitrobenzoic acid esters, 2-amino-3-chloro-5-nitrobenzoic acid esters, 2-amino-3,5-dichlorobenzoic acid esters, 2-amino-3,5-dibromobenzoic acid esters, methyl 2-amino-3,5-dinitrobenzoate, .beta.-methoxyethyl 2-amino-3,5-dinitrobenzoate, diethyl-2-aminoterephthalate, 4-aminoazobenzene, 2,3'-dimethyl-4-aminoazobenzene, 2',3-dimethyl-4-aminoazobenzene, 2,5-dimethyl-4-aminoazobenzene and 3,5-dibromo-4-aminoazobenzene.

The following are paricularly valuable heterocyclic diazo components: 2-amino-5-nitrothiazole, 2-amino-4-methyl-5-nitrothiazole, 2-amino-4-methylthiazole-5-carboxylic acid ethyl ester, 2-amino-5-phenyl-1,3,4-thiadiazole, 3-phenyl-5-amino-1,2,4-thiadiazole, 3-methylmercapto-5-amino-1,2,4-thiadiazole, 3-.beta.-carbomethoxyethylmercapto-5-amino-1,2,4-thiadiazole, 3-.beta.-carboethoxyethylamercapto-5-amino-1,2,4-thiadiazole, 2-amino-6-cyanobenzothiazole, 2-amino-6-carboxylic methyl ester benzothiazole, 2-amino-6-nitrobenzothiazole, 2-amino-3-cyano-4-methylthiophene-5-carboxylic esters, 3-amino-5-nitro-2,1-benzoisothiazole, 3-amino-5-nitro-7-chloro-2,1-benzoisothiazole, 3-amino-5-nitro-7-bromo-2,1-benzoisothiazole, 4-amino-7-nitro-1,2-benzoisothiazole, 4-amino-5-bromo-1,2-benzoisothiazole, 4-amino-5-bromo-7-nitro-1,2-benzoisothiazole, 4-amino-5-cyano-7-nitro-1,2-benzoisothiazole and 4-amino-5-chloro-7-nitro-1,2-benzoisothiazole.

The new dyes are yellow to blue and are suitable for coloring textile materials of acrylonitrile polymers, synthetic polyamides, cellulose esters such as secondary cellulose acetate or cellulose triacetate, and particularly linear polyesters such as polyethylene glycol terephthalate or polymers having a similar chemical constitution. Deep colorations are obtained which are distinguished by outstanding fastness properties.

The following Examples illustrate the invention. Parts and percentages are by weight unless otherwise stated.

EXAMPLE 1

A mixture of 187 parts of 2,6-dichloro-3-cyano-4-methylpyridine, 200 parts of isopropanol and 300 parts of aniline is stirred for eight hours at about 90.degree. C to 100.degree. C. The mixture is allowed to cool and poured while stirring into about 1500 parts of water, 200 parts of concentrated hydrochloric acid and 200 parts of ice. Stirring is continued for another hour and the deposited precipitate which probably has the formula: ##STR29## is suction filtered, washed with water until neutral and dried. About 240 parts of a colorless powder is obtained which melts at 135.degree. to 140.degree. C.

12.2 parts of this powder is stirred with 40 parts of .gamma.-hydroxypropylamine for six hours at 245.degree. to 160.degree. C. The mixture is then allowed to cool and after 100 parts of water has been added it is acidified with hydrochloric acid to a pH of from about 0 to 1. If necessary a little glacial acetic acid or dimethylformamide is added and a solution of the coupling component of the probable formula: ##STR30## is obtained. A solution or suspension of this coupling component is cooled to 0.degree. to 3.degree. C by adding ice and a diazonium salt soultion is added which is obtained as follows: 6.9 parts of p-nitroaniline has added to it about 30 parts of concentrated hydrochloric acid (30%) and 80 parts of water, the mixture is cooled to 0.degree. C and 15 parts by volume of 23% sodium nitrite solution is added in portions. The whole is stirred for another two hours, any excess of nitrous acid present is removed in the usual way and the product is filtered.

The filtrate is added to the coupling mixture and then such an amount of sodium acetate or caustic soda solution is added gradually while stirring until the pH of the coupling mixture is from about 2 to 3. Ice-water may be added to the mixture if it is difficult to stir. After coupling is over the mixture is heated to 70.degree. to 80.degree. C, filtered, washed with water and dried. About 20 parts of a reddish brown powder is obtained of the probable formula: ##STR31## which dissolves in dimethylformamide with a red color and dyes polyethylene terephthalate cloth full, clear yellowish red shades having outstanding fastness properties.

The following dyes characterized by the diazo and coupling components may be obtained in an analogous manner.

TABLE 1__________________________________________________________________________Coupling component: ##STR32##__________________________________________________________________________Example No. Diazo component R.sup.2 Shade__________________________________________________________________________ ##STR33## CH.sub.2CH.sub.2CH.sub.2OCH.sub.3 reddish yellow3 CH.sub.2CH.sub.2OH yellow4 CH.sub.2C.sub.2CH.sub.2OH reddish yellow5 ##STR34## reddish yellow6 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH reddish yellow7 CH.sub.2CH.sub.2OCH.sub.3 yellow__________________________________________________________________________ ##STR35## H reddish yellow9 CH.sub.2CH.sub.2OH reddish yellow10 CH.sub.2CH.sub.2CH.sub.2OH reddish yellow11 ##STR36## reddish yellow12 CH.sub.2CH.sub. 2OCH.sub.2CH.sub.2OH reddish__________________________________________________________________________ yellow13 ##STR37## H reddish yellow14 CH.sub.2CH.sub.2OH yellow15 CH.sub.2CH.sub.2CH.sub.2OH yellow16 ##STR38## yellow17 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellow__________________________________________________________________________18 ##STR39## H yellow19 CH.sub.2CH.sub.2OH yellow20 CH.sub.2CH.sub.2CH.sub.2OH yellow21 ##STR40## yellow22 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellow__________________________________________________________________________23 ##STR41## H reddish orange24 CH.sub.2CH.sub.2OH yellowish red25 CH.sub.2CH.sub.2CH.sub.2OH yellowish red26 ##STR42## yellowish red27 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellowish__________________________________________________________________________ red28 ##STR43## H reddish orange29 CH.sub.2CH.sub.2OH yellowish red30 CH.sub.2CH.sub.2CH.sub.2OH yellowish red31 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellowish__________________________________________________________________________ red32 ##STR44## H orange33 CH.sub.2CH.sub.2OH yellowish red34 CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3 yellowish red35 ##STR45## yellowish red36 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellowish red37 CH.sub.2CH.sub.2OCH.sub.3 yellowish red38 CH.sub.2CH.sub.2CH.sub.2OCH.sub.3 yellowish red39 CH.sub.2CH.sub.2OCHO reddish orange- yellowish red40 (CH.sub.2).sub.6OH yellowish__________________________________________________________________________ red41 ##STR46## H yellowish red42 CH.sub.2CH.sub.2OH yellowish red43 CH.sub.2CH.sub.2CH.sub.2OH yellowish red44 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH red45 ##STR47## red46 CH.sub.2CH.sub.2CH.sub.2OCH.sub.3 red47 CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3 red__________________________________________________________________________48 ##STR48## CH.sub.2CH.sub.2OH yellowish red49 CH.sub.2CH.sub.2CH.sub.2OH yellowish red50 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellowish__________________________________________________________________________ red51 ##STR49## CH.sub.2CH.sub.2OH red52 CH.sub.2CH.sub.2CH.sub.2OH red53 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH red__________________________________________________________________________54 ##STR50## CH.sub.2CH.sub.2OH yellowish red55 CH.sub.2CH.sub.2CH.sub.2OH yellowish red56 ##STR51## CH.sub.2CH.sub.2OH reddish yellow57 CH.sub.2CH.sub.2CH.sub.2OH reddish yellow58 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH reddish__________________________________________________________________________ yellow59 ##STR52## CH.sub.2CH.sub.2OH reddish orange60 CH.sub.2CH.sub.2CH.sub.2OH reddish orange61 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH reddish__________________________________________________________________________ orange62 ##STR53## CH.sub.2CH.sub.2OH orange63 CH.sub.2CH.sub.2CH.sub.2OH orange64 CH.sub.2CH.sub. 2OCH.sub.2CH.sub.2OH orange__________________________________________________________________________65 ##STR54## H orange66 CH.sub.2CH.sub.2OH orange67 CH.sub.2CH.sub.2CH.sub.2OH orange68 CH.sub.2CH.sub.2CH.sub.2OCH.sub.3 orange__________________________________________________________________________69 ##STR55## CH.sub.2CH.sub.2OH yellow70 CH.sub.2CH.sub.2CH.sub.2OH yellow71 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2 OH yellow__________________________________________________________________________72 ##STR56## H yellow73 CH.sub.2CH.sub.2OH orange74 CH.sub.2CH.sub.2CH.sub.2OH orange75 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2 OH orange76 CH.sub.2CH.sub.2OCH.sub.3 orange__________________________________________________________________________77 ##STR57## CH.sub.2CH.sub.2CH.sub.2OH red78 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH red__________________________________________________________________________79 ##STR58## CH.sub.2CH.sub.2CH.sub.2OH yellowish red80 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellowish__________________________________________________________________________ red81 ##STR59## CH.sub.2CH.sub.2OH orange82 CH.sub.2CH.sub.2CH.sub.2OH orange83 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH orange__________________________________________________________________________84 ##STR60## CH.sub.2CH.sub.2OH orange85 CH.sub.2CH.sub.2CH.sub.2OH orange86 ##STR61## orange87 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH orange__________________________________________________________________________88 ##STR62## CH.sub.2CH.sub.2OH yellowish orange89 CH.sub.2CH.sub.2CH.sub.2OH yellowish orange90 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellowish orange__________________________________________________________________________91 ##STR63## CH.sub.2CH.sub.2OH orange92 CH.sub.2CH.sub.2CH.sub.2OH orange__________________________________________________________________________93 ##STR64## CH.sub.2CH.sub.2OH orange94 CH.sub.2CH.sub.2CH.sub.2OH orange__________________________________________________________________________ TABLE 2__________________________________________________________________________Coupling component: ##STR65##__________________________________________________________________________Example No. Diazo component R.sup.1 Shade__________________________________________________________________________95 ##STR66## CH.sub.2CH.sub.2OH reddish yellow96 CH.sub.2CH.sub.2CH.sub.2OH reddish yellow97 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH reddish yellow__________________________________________________________________________98 ##STR67## CH.sub.2CH.sub.2OH yellow99 CH.sub.2CH.sub.2CH.sub.2OH yellow100 CH.sub.2CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellow__________________________________________________________________________101 ##STR68## CH.sub.2CH.sub.2OH yellow102 CH.sub.2CH.sub.2CH.sub.2OH yellow103 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellow__________________________________________________________________________104 ##STR69## CH.sub.2CH.sub.2OH yellowish red105 CH.sub.2CH.sub.2CH.sub.2OH yellowish red106 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellowish red__________________________________________________________________________107 ##STR70## CH.sub.2CH.sub.2CH.sub.2OH yellowish red108 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellowish red__________________________________________________________________________109 ##STR71## CH.sub.2CH.sub.2CH.sub.2OH red110 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH red__________________________________________________________________________111 ##STR72## CH.sub.2CH.sub.2CH.sub.2OH yellow112 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellow__________________________________________________________________________113 ##STR73## CH.sub.2CH.sub. 2OH orange114 CH.sub.2CH.sub.2CH.sub.2OH orange115 CH.sub.2CH.sub.2CH.sub.2OCH.sub.3 orange__________________________________________________________________________

EXAMPLE 116

24.4 parts of the reaction product of aniline with 2,6-dichloro-3-cyano-4-methylpyridine (see Example 1) is stirred with 80 parts of .gamma.-methoxypropylamine for eight hours under superatmospheric pressure at 140.degree. to 160.degree. C and then allowed to cool. 8 parts of 50% caustic soda solution is added and excess .gamma.-methoxypropylamine and water are distilled off. The residue is treated with 100 parts of 85% sulfuric acid for five hours at 100.degree. C and allowed to cool. The mixture is poured into a mixture of about 500 parts of water, 600 parts of ice and 100 parts of 50% caustic soda solution. The mixture, which contains the coupling component of the probable formula: ##STR74## is cooled to 0.degree. C and a solution of diazotized 3-amino-5-nitro-2,1-benzothiazole (prepared as follows) is then added in portions; 19.5 parts of 3-amino-5-nitro-2,1-benzoisothiazole is added in portions while stirring at 15.degree. to 25.degree. C to about 75 to 85 parts of 96% sulfuric acid and the whole is cooled to 0.degree. to 4.degree. C. 32.5 parts of 23% nitrosylsulfuric acid is then dripped in at the said temperature. Diazotization is over after stirring for about four hours at 0.degree. to 5.degree. C. After the diazonium solution has been added to the coupling mixture the pH of the mixture is raised to about 1.5 to 2.5 by adding an acid-binding agent such as sodium acetate (or caustic soda solution). It is convenient to add ice and ice-water to achieve efficient stirring at 0.degree. to 5.degree. C. After coupling is over the mixture is heated to 60.degree. to 80.degree. C and the precipitated dye is suction filtered, washed with hot water and dried. About 40 parts of a black dye powder of the probable formula: ##STR75## is obtained which dissolves in dimethylformamide with a blue color and dyes polyethylene terephthalate cloth greenish blue shades having very good fastness properties.

EXAMPLE 117

122 parts of the reaction product of aniline with 2,6-dichloro-3-cyano-4-methylpyridine (see Example 1) is treated with 150 parts of N-methylpyrrolidone and about 1000 parts of 25% ammonia for fifteen hours at 180.degree. C in an autoclave. After cooling the precipitated product having the probable formula: ##STR76## is filtered, washed with water and dried. About 108 parts of a colorless product is obtained.

22.4 parts of this product is dissolved in about 100 parts of glacial acetic acid, then cooled to 0.degree. to 2.degree. C with ice and some sulfamic acid is added. A solution of diazotized 2-amino-5-nitrobenzonitrile is added in portions to this coupling mixture at 0.degree. C. The diazo solution is prepared as follows: 16.3 parts of 2-amino-5-nitrobenzonitrile is added in portions to a mixture, cooled to 0.degree. C, of about 90 parts of 96% sulfuric acid and 32.5 parts of 23% nitrosylsulfuric acid. After stirring for about four to five hours at 0.degree. to 4.degree. C the diazotization is over.

In order to carry out coupling rapidly and completely the coupling mixture (which may be diluted with ice and ice-water) is adjusted at 0.degree. to 5.degree. C to pH about 2.5 by adding sodium acetate solution. After coupling is over the mixture is heated to about 80.degree. C, the precipitated dye of the probable formula: ##STR77## is filtered off, washed with hot water and dried. About 38 parts of a dark brown powder is obtained which dissolves in dimethylformamide with a red color and dyes polyethylene terephthalate cloth full pink to red shades having excellent fastness properties.

The dyes characterized in the following Table by the diazo and coupling components may be obtained analogously to the methods described in Example 1, 116 and 117.

TABLE 3__________________________________________________________________________Coupling component ##STR78##__________________________________________________________________________Example No. Diazo component R.sup.2 Shade__________________________________________________________________________118 ##STR79## CH.sub.2CH.sub.2OH pink119 CH.sub.2 CH.sub.2CH.sub.2OH pink120 ##STR80## pink121 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH pink122 CH.sub.2CH.sub.2CH.sub.2OCHO pink123 CH.sub.2CH.sub.2OCH.sub.3 pink124 (CH.sub.2).sub.6OH pink125 CH.sub.2CH.sub. 2OCOCH.sub.3 pink__________________________________________________________________________126 ##STR81## CH.sub.2CH.sub.2OH red127 CH.sub.2CH.sub.2CH.sub.2OH red128 ##STR82## red129 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH red130 CH.sub.2CH.sub.2OCH.sub.3 yellowish__________________________________________________________________________ red131 ##STR83## H red132 CH.sub.2CH.sub.2OH red133 CH.sub.2CH.sub.2CH.sub.2OH red134 ##STR84## red135 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH red136 CH.sub.2CH.sub.2OCH.sub.3 red137 CH.sub.2CH.sub.2CH.sub.2OCH.sub.3 red138 CH.sub.2CH.sub.2OCOCH.sub.3 red__________________________________________________________________________139 ##STR85## H red140 CH.sub.2CH.sub.2OH red141 CH.sub.2CH.sub.2CH.sub.2OH red142 ##STR86## red143 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH red144 CH.sub.2CH.sub.2OCH.sub.3 red145 C.sub.2 H.sub.5 red__________________________________________________________________________146 ##STR87## CH.sub.2CH.sub.2OH red147 CH.sub.2CH.sub.2CH.sub.2OH red148 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH red__________________________________________________________________________149 ##STR88## CH.sub.2CH.sub.2OH red150 CH.sub.2CH.sub.2CH.sub.2OH red151 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH red__________________________________________________________________________152 ##STR89## CH.sub.2CH.sub.2OH red153 CH.sub.2CH.sub.2CH.sub.2OH red__________________________________________________________________________154 ##STR90## H red155 CH.sub.2CH.sub.2OH red156 CH.sub.2CH.sub.2CH.sub.2OH red157 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH red158 CH.sub.2CH.sub.2OCH.sub.3 red__________________________________________________________________________159 ##STR91## CH.sub.2CH.sub.2OH reddish brown160 CH.sub.2CH.sub.2CH.sub.2OH reddish brown161 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH reddish brown162 CH.sub.2CH.sub.2OCOCH.sub.3 reddish brown__________________________________________________________________________163 ##STR92## CH.sub.2CH.sub.2OH reddish brown164 CH.sub.2CH.sub.2CH.sub.2OH reddish brown165 ##STR93## reddish brown166 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH reddish brown__________________________________________________________________________167 ##STR94## CH.sub.2CH.sub.2OH reddish brown168 CH.sub.2CH.sub.2CH.sub.2OH reddish brown169 CH.sub.2CH.sub.2CH.sub.2OCH.sub.3 reddish brown__________________________________________________________________________170 ##STR95## CH.sub.2CH.sub.2OH violet171 CH.sub.2CH.sub.2CH.sub.2OH violet172 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH violet173 CH.sub.2CH.sub.2CH.sub.2OCH.sub.3 violet__________________________________________________________________________174 ##STR96## CH.sub.2CH.sub.2OH bluish red175 CH.sub.2CH.sub.2CH.sub.2OH bluish red__________________________________________________________________________176 ##STR97## CH.sub.2CH.sub.2OH bluish red177 CH.sub.2CH.sub.2CHOH bluish red178 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH bluish red__________________________________________________________________________179 ##STR98## CH.sub.2CH.sub.2OH orange180 CH.sub.2CH.sub.2CH.sub.2OH orange181 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH orange__________________________________________________________________________182 ##STR99## CH.sub.2CH.sub.2OH orange183 CH.sub.2CH.sub.2CH.sub.2OH orange184 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH orange__________________________________________________________________________185 ##STR100## H bluish red186 CH.sub.2CH.sub.2OH red187 CH.sub.2CH.sub.2CH.sub.2OH red188 ##STR101## red189 (CH.sub.2).sub.3O(CH.sub.2).sub.4OH red__________________________________________________________________________190 ##STR102## CH.sub.2CH.sub.2OH reddish blue191 CH.sub.2CH.sub.2CH.sub.2OH navy192 ##STR103## navy193 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH navy194 (CH.sub.2).sub.6OH navy195 (CH.sub.2).sub.3O(CH.sub.2).sub.4OH navy196 ##STR104## reddish blue__________________________________________________________________________197 ##STR105## CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH blue__________________________________________________________________________198 ##STR106## CH.sub.2CH.sub.2CH.sub.2OH reddish brown199 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH reddish brown__________________________________________________________________________200 ##STR107## CH.sub.2CH.sub.2CH.sub.2OH yellow201 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellow__________________________________________________________________________202 ##STR108## CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellow203 (CH.sub.2).sub.3OH yellow__________________________________________________________________________204 ##STR109## CH.sub.2CH.sub.2OH violet205 CH.sub.2CH.sub.2CH.sub.2OH violet206 ##STR110## violet207 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH violet__________________________________________________________________________208 ##STR111## (CH.sub.2).sub.3OH violet209 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH violet__________________________________________________________________________210 ##STR112## CH.sub.2CH.sub.2CH.sub.2OH yellowish red211 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellowish__________________________________________________________________________ red212 ##STR113## CH.sub.2CH.sub.2CH.sub.2OH yellowish red213 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellowish__________________________________________________________________________ red214 ##STR114## CH.sub.2CH.sub.2CH.sub.2OH yellowish red215 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellowish__________________________________________________________________________ red216 ##STR115## CH.sub.2CH.sub.2OH red217 CH.sub.2CH.sub.2CH.sub.2OH red218 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH red219 (CH.sub.2).sub.3O(CH.sub.2).sub.4OH red__________________________________________________________________________220 ##STR116## CH.sub.2CH.sub.2CH.sub.2OH violet221 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH violet222 (CH.sub.2).sub.3O(CH.sub.2).sub.4OH violet__________________________________________________________________________223 ##STR117## CH.sub.2CH.sub.2CH.sub.2OH violet224 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH violet__________________________________________________________________________225 ##STR118## CH.sub.2CH.sub.2CH.sub.2OH violet226 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH violet__________________________________________________________________________227 ##STR119## CH.sub.2CH.sub.2CH.sub.2OH red__________________________________________________________________________228 ##STR120## H reddish orange229 CH.sub.2CH.sub.2OH yellowish red230 CH.sub.2CH.sub.2CH.sub.2OH yellowish red231 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellowish__________________________________________________________________________ red232 ##STR121## CH.sub.2CH.sub.2OH yellowish red233 CH.sub.2CH.sub.2CH.sub.2OH yellowish red234 ##STR122## yellowish red235 CHCHOCHCHOH yellowish red236 H reddish orange__________________________________________________________________________237 ##STR123## CH.sub.2CH.sub.2OH violet238 CH.sub.2CH.sub.2CH.sub.2OH violet239 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH violet__________________________________________________________________________240 ##STR124## CH.sub.2CH.sub.2OH bluish red241 CH.sub.2CH.sub.2CH.sub.2OH reddish violet242 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH reddish violet243 ##STR125## reddish violet__________________________________________________________________________244 ##STR126## CH.sub.2CH.sub.2OH reddish violet245 CH.sub.2CH.sub.2CH.sub.2OH reddish violet246 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH reddish violet__________________________________________________________________________247 ##STR127## CH.sub.2CH.sub.2CH.sub.2OH red__________________________________________________________________________248 ##STR128## CH.sub.2CH.sub.2CH.sub.2OH violet249 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH violet__________________________________________________________________________250 ##STR129## CH.sub.2CH.sub.2OH reddish blue251 CH.sub.2CH.sub.2CH.sub.2OH reddish blue252 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH reddish blue__________________________________________________________________________253 ##STR130## CH.sub.2CH.sub.2CH.sub.2OH blue__________________________________________________________________________ TABLE 4__________________________________________________________________________Coupling component ##STR131##Example No. Diazo component R.sup.1 Shade__________________________________________________________________________254 ##STR132## CH.sub.2CH.sub.2OH red255 CH.sub.2CH.sub.2CH.sub.2OH red256 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH red__________________________________________________________________________257 ##STR133## H pink258 CH.sub.2CH.sub.2OH red259 CH.sub.2CH.sub.2OCOCH.sub.3 pink260 CH.sub.2CH.sub.2CH.sub.2OH red261 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH pink262 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCHO pink263 (CH.sub.2).sub.6OH red__________________________________________________________________________264 ##STR134## CH.sub.2CH.sub.2CH.sub.2OH red265 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH red__________________________________________________________________________266 ##STR135## H red267 CH.sub.2CH.sub.2OH red268 CH.sub.2CH.sub.2CH.sub.2OH red269 ##STR136## red270 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH red__________________________________________________________________________271 ##STR137## CH.sub.2CH.sub.2OH red272 CH.sub.2CH.sub.2CH.sub.2OH red273 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2 OH red274 (CH.sub.2).sub.3O(CH.sub.2).sub.4OH red__________________________________________________________________________275 ##STR138## CH.sub.2CH.sub.2CH.sub.2OH violet__________________________________________________________________________276 ##STR139## CH.sub.2CH.sub.2CH.sub.2OH red277 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH red__________________________________________________________________________278 ##STR140## CH.sub.2CH.sub.2CH.sub.2OH violet279 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH violet__________________________________________________________________________280 ##STR141## CH.sub.2CH.sub.2CH.sub.2OH navy281 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH navy__________________________________________________________________________282 ##STR142## CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH blue283 ##STR143## CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH blue__________________________________________________________________________284 ##STR144## CH.sub.2CH.sub.2OH red285 CH.sub.2CH.sub.2CH.sub.2OH red286 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH red__________________________________________________________________________287 ##STR145## CH.sub.2CH.sub.2CH.sub.2OH violet288 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH violet__________________________________________________________________________289 ##STR146## CH.sub.2CH.sub.2CH.sub.2OH violet290 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH violet__________________________________________________________________________291 ##STR147## CH.sub.2CH.sub.2OCH.sub.2CH.sub. red__________________________________________________________________________ TABLE 5__________________________________________________________________________Coupling component: ##STR148##__________________________________________________________________________Example No. Diazo component R.sup.2 Shade__________________________________________________________________________293 ##STR149## CH.sub.2CH.sub.2OCOCH.sub.3 red294 CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3 red295 CH.sub.2CH.sub.2CH.sub.2OH red296 CH.sub.2CH.sub.2OCH.sub.3 red__________________________________________________________________________297 ##STR150## CH.sub.2CH.sub.2OCOCH.sub.3 bluish red298 CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3 bluish red299 CH.sub.2CH.sub.2CH.sub.2OH bluish red300 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCOCH.sub.3 bluish red301 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2 OH bluish red302 CH.sub.2CH.sub.2OCH.sub.3 bluish red__________________________________________________________________________303 ##STR151## CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3 violet304 CH.sub.2CH.sub.2CH.sub.2OH violet305 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCOCH.sub.3 violet306 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH violet307 CH.sub.2CH.sub.3 violet308 CH.sub.2CH.sub.2CH.sub.2OCH.sub.3 violet__________________________________________________________________________309 ##STR152## CH.sub.2CH.sub.2OCOCH.sub.2COCH.sub.3 greenish blue310 CH.sub.2CH.sub.2OCOCH.sub.3 greenish blue311 CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3 greenish blue312 CH.sub.2CH.sub.2CH.sub.2OH greenish blue313 CH.sub.2CH.sub.2OCH.sub.3 greenish blue314 CH.sub.2CH.sub.2CH.sub.2OC.sub.2 H.sub.5 greenish blue315 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCHO greenish blue316 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH greenish blue317 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCOCH.sub.3 greenish blue__________________________________________________________________________318 ##STR153## CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCOCH.sub.3 greenish blue__________________________________________________________________________ TABLE 6__________________________________________________________________________Coupling compoent: ##STR154##Example No. Diazo component R.sup.1 Shade__________________________________________________________________________319 ##STR155## CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3 red320 CH.sub.2CH.sub.2CH.sub.2OH red__________________________________________________________________________321 ##STR156## CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3 bluish red322 CH.sub.2CH.sub.2CH.sub.2OH bluish red323 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCOCH.sub.3 bluish red324 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCHO bluish red__________________________________________________________________________325 ##STR157## CH.sub.2CH.sub.2CH.sub.2O COCH.sub.3 violet326 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCHO violet327 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCOCH.sub.3 violet__________________________________________________________________________328 ##STR158## CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3 greenish blue329 CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.2COCH.sub.3 greenish blue330 CH.sub.2CH.sub.2CH.sub.2OH greenish blue331 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH greenish blue332 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCHO greenish blue333 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCOCH.sub.3 greenish__________________________________________________________________________ blue334 ##STR159## CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCHO greenish blue335 CH.sub.2CH.sub.2OCH.sub.2CH.sub. greenish blue336 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH greenish blue337 (CH.sub.2).sub.3O(CH.sub.2).sub.4OH greenish__________________________________________________________________________ blue338 ##STR160## CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCOCH.sub.3 greenish blue339 CH.sub.2CH.sub.2OCH.sub.3 greenish__________________________________________________________________________ blue The following dyes may be prepared analogously: __________________________________________________________________________Example No.340 ##STR161## red341 ##STR162## bluish red342 ##STR163## orange343 ##STR164## yellowish__________________________________________________________________________ red

EXAMPLE 344

11 parts of the dye of the formula: ##STR165## is heated under reflux with 100 parts by volume of formic acid for four hours. After cooling about 100 parts of water is added with stirring and the precipitate of the formula: ##STR166## which is thrown down is filtered, washed with water and dried. About 11 parts of a brown powder is obtained which dissolves in dimethylformamide with a red color and dyes polyethylene terephthalate cloth pink to red shades of outstanding fastness properties.

EXAMPLE 345

A mixture of 187 parts of 2,6-dichloro-3-cyano-4-methylpyridine, 200 parts of isopropanol and 300 parts of 2-phenylpropylamine is stirred for eight hours at about 45.degree. to 55.degree. C. The mixture is then allowed to cool and is poured with stirring into about 1500 parts of water, 200 parts of concentrated hydrochloric acid and 200 parts of ice. The whole is stirred for another hour and the deposited precipitate of the probable formula: ##STR167## is suction filtered, washed with water until neutral and dried. About 240 parts of a colorless powder is obtained which melts at 100.degree. to 105.degree. C.

15 parts of this powder is stirred with 40 parts of .beta.-hydroxyethylamine for six hours at 145.degree. to 160.degree. C. The mixture is then allowed to cool and is acidified with hydrochloric acid to a pH of from about 0 to 1. If necessary some glacial acetic acid or dimethylformamide is added. A solution of the coupling component of the probable formula: ##STR168## is obtained.

The solution or suspension of this coupling component is cooled to 0.degree. to 3.degree. C by adding ice and a diazonium salt solution is added which has been obtained as follows:

6.9 parts of p-nitroaniline has about 30 parts of concentrated hydrochloric acid (30%) and 80 parts of water added to it and the mixture is then cooled to 0.degree. C and 15 parts by volume of 23% sodium nitrite solution is added in portions. The whole is stirred for another two hours, any excess of nitrous acid present is removed in the usual way, and the whole is filtered.

The filtrate is added to the coupling mixture and then while stirring such an amount of sodium acetate is gradually added that the pH of the coupling mixture is from about 2 to 3. If the mixture is difficult to stir ice-water may be added. When the coupling is ended the mixture is heated to 70.degree. to 80.degree. C, filtered, washed with water and dried. About 20 parts of a brown powder of the probable formula: ##STR169## is obtained which dissolves in dimethylformamide with an orange color and dyes polyethylene terephthalate cloth full, clear orange shades of outstanding fastness properties.

The following dyes characterized by the diazo and coupling components may be obtained analogously to the methods described:

TABLE 1__________________________________________________________________________ ##STR170##__________________________________________________________________________Example No. Diazo component R.sup.2 Shade__________________________________________________________________________346 ##STR171## H yellow347 CH.sub.2CH.sub.2OH yellow348 CH.sub.2CH.sub.2OH yellow349 ##STR172## yellow350 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellow351 CH.sub.2CH.sub.2OCH.sub.3 yellow__________________________________________________________________________352 ##STR173## H yellow353 CH.sub.2CH.sub.2OH yellow354 CH.sub.2CH.sub.2CH.sub.2OH yellow355 ##STR174## yellow356 CH.sub.2CH.sub.2OCH.sub. yellowb.2OH__________________________________________________________________________357 ##STR175## H yellow358 CH.sub.2CH.sub.2OH yellow359 CH.sub.2CH.sub.2CH.sub.2OH yellow360 ##STR176## yellow361 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellow__________________________________________________________________________362 ##STR177## yellow363 CH.sub.2CH.sub.2OH yellow364 CH.sub.2CH.sub.2CH.sub.2OH yellow365 ##STR178## yellow366 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellow__________________________________________________________________________367 ##STR179## H orange368 CH.sub.2CH.sub.2OH orange369 CH.sub.2CH.sub.2CH.sub.2OH orange370 ##STR180## orange371 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH orange__________________________________________________________________________372 ##STR181## H orange373 CH.sub.2CH.sub.2OH orange374 CH.sub.2CH.sub.2CH.sub.2OH orange375 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH orange__________________________________________________________________________376 ##STR182## H orange377 CH.sub.2CH.sub.2OH orange378 CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3 orange379 ##STR183## orange380 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH orange381 CH.sub.2CH.sub.2OCH.sub.3 orange382 CH.sub.2CH.sub.2CH.sub.2OCH.sub.3 orange383 CH.sub.2CH.sub.2OCHO orange384 (CH.sub.2).sub.6OH orange__________________________________________________________________________385 ##STR184## H yellowish red386 CH.sub.2CH.sub.2OH yellowish red387 CH.sub.2CH.sub.2CH.sub.2OH yellowish red388 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellowish red389 ##STR185## yellowish red390 CH.sub.2CH.sub.2CH.sub.2OCH.sub.3 yellowish red391 CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3 yellowish__________________________________________________________________________ red392 ##STR186## CH.sub.2CH.sub.2OH yellowish red393 CH.sub.2CH.sub.2CH.sub.2OH yellowish red394 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellowish__________________________________________________________________________ red395 ##STR187## CH.sub.2CH.sub.2OH yellowish red396 CH.sub.2CH.sub.2OH yellowish red397 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellowish__________________________________________________________________________ red398 ##STR188## CH.sub.2CH.sub.2OH orange399 CH.sub.2CH.sub.2CH.sub.2OH orange__________________________________________________________________________400 ##STR189## CH.sub.2CH.sub.2OH yellow401 CH.sub.2CH.sub.2CH.sub.2OH yellow402 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellow__________________________________________________________________________403 ##STR190## CH.sub.2CH.sub.2OH orange404 CH.sub.2CH.sub.2CH.sub.2OH orange405 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH orange__________________________________________________________________________406 ##STR191## CH.sub.2CH.sub.2OH yellow407 CH.sub.2CH.sub.2CH.sub.2OH yellow408 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellow__________________________________________________________________________409 ##STR192## H yellow410 CH.sub.2CH.sub.2 OH yellow411 CH.sub.2CH.sub.2OH yellow412 CH.sub.2CH.sub.2CH.sub.2OCH.sub.3 yellow__________________________________________________________________________413 ##STR193## CH.sub.2CH.sub.2OH yellow414 CH.sub.2CH.sub.2CH.sub.2OH yellow415 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellow__________________________________________________________________________416 ##STR194## H yellow417 CH.sub.2CH.sub.2OH yellow418 CH.sub.2CH.sub.2CH.sub.2OH yellow419 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellow420 CH.sub.2CH.sub.2OCH.sub.3 yellow__________________________________________________________________________421 ##STR195## CH.sub.2CH.sub.2CH.sub.2OH yellowish red422 CH.sub.2CH.sub.2OH yellowish__________________________________________________________________________ red423 ##STR196## CH.sub.2CH.sub.2CH.sub.2OH orange424 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH orange__________________________________________________________________________425 ##STR197## CH.sub.2CH.sub.2OH yellow426 CH.sub.2CH.sub.2CH.sub.2OH yellow427 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellow__________________________________________________________________________428 ##STR198## CH.sub.2CH.sub.2OH yellow429 CH.sub.2CH.sub.2CH.sub.2OH yellow430 ##STR199## yellow431 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellow__________________________________________________________________________432 ##STR200## CH.sub.2CH.sub.2OH yellow433 CH.sub.2CH.sub.2CH.sub.2OH yellow__________________________________________________________________________434435 ##STR201## CH.sub.2CH.sub.2OH yellow436 CH.sub.2CH.sub.2CH.sub.2OH yellow__________________________________________________________________________437 ##STR202## CH.sub.2CH.sub.2OH yellow438 CH.sub.2CH.sub.2CH.sub.2OH yellow__________________________________________________________________________ TABLE 2__________________________________________________________________________Coupling component: ##STR203##Example Diazo component R.sub.1 Shade__________________________________________________________________________439 ##STR204## CH.sub.2CH.sub.2OH yellow440 CH.sub.2CH.sub.2CH.sub.2OH yellow441 H yellow__________________________________________________________________________442 ##STR205## CH.sub.2CH.sub.2OH yellow443 CH.sub.2CH.sub.2CH.sub.2OH yellow444 CH.sub.2CH.sub.2CH.sub.2O(CH.sub.2).sub.2 OH yellow__________________________________________________________________________445 ##STR206## CH.sub.2CH.sub.2OH yellow446 CH.sub.2CH.sub.2CH.sub.2OH yellow447 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellow__________________________________________________________________________448 ##STR207## CH.sub.2CH.sub.2OH orange449 CH.sub.2CH.sub.2CH.sub.2OH orange450 CH.sub.2CH.sub.2O(CH.sub.2).sub.2OH orange__________________________________________________________________________451 ##STR208## CH.sub.2CH.sub.2CH.sub.2OH orange452 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH orange__________________________________________________________________________453 ##STR209## CH.sub.2CH.sub.2OH yellowish red454 CH.sub.2CH.sub.2CH.sub.2OH yellowish red__________________________________________________________________________455 ##STR210## CH.sub.2CH.sub.2CH.sub.2OH yellow456 CH.sub.2CH.sub.2O(CH.sub.2).sub.2 OH yellow__________________________________________________________________________457 ##STR211## CH.sub.2CH.sub.2OH yellow458 CH.sub.2CH.sub.2CH.sub.2OH yellow459 CH.sub.2CH.sub.2CH.sub.2CH.sub.3 yellow__________________________________________________________________________

EXAMPLE 460

19.5 parts of 3-amino-5-nitro-2,1-benzoisothiazole is added in portions while stirring at 15.degree. to 25.degree. C to about 75 to 85 parts of 96% sulfuric acid and the mixture is cooled to 0.degree. to 4.degree. C. 32.5 parts of 23% nitrosylsulfuric acid is then dripped in at this temperature. Diazotization is over after stirring for about three to four hours at 0.degree. to 5.degree. C. The diazonium salt mixture is then added to a solution or suspension, cooled to 0.degree. C, of 34 parts of the coupling component of the formula: ##STR212## in 50 parts of 30% hydrochloric acid, 500 parts of water and 150 parts of glacial acetic acid. Ice and sodium acetate are added gradually during the coupling so that the temperature of the coupling mixture does not exceed 5.degree. C and the pH finally is about 2. The precipitated dye of the formula: ##STR213## is filtered off, washed with hot water and dried. About 53 parts of a black powder is obtained which dissolves in dimethylformamide with a reddish blue color.

EXAMPLE 461

50 parts of the powder obtained in Example 460 is stirred with about 200 parts of 85 to 95% sulfuric acid for five hours at from 80.degree. to 100.degree. C. The mixture is then poured onto 1500 parts of ice-water, and the precipitated dye of the formula: ##STR214## is filtered off, washed with water and dried. About 40 parts of a dark powder is obtained which dissolves in dimethylformamide with a blue color and dyes polyethylene terephthalate cloth blue shades.

Dyes characterized in the following Table by the diazo and coupling components may be obtained by methods analogous to those described above:

TABLE 3__________________________________________________________________________Coupling component: ##STR215##__________________________________________________________________________Example Diazo component R.sup.2 Shade__________________________________________________________________________462 ##STR216## CH.sub.2CH.sub.2OH yellowish red463 CH.sub.2CH.sub.2CH.sub.2OH yellowish red464 ##STR217## yellowish red465 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellowish red466 CH.sub.2CH.sub.2CH.sub.2OCHO yellowish red467 H yellowish red468 (CH.sub.2).sub.6OH yellowish red469 CH.sub.2CH.sub.2OCOCH.sub.3 yellowish red red__________________________________________________________________________470 ##STR218## CH.sub.2CH.sub.2OH yellowish red471 CH.sub.2CH.sub.2CH.sub.2OH yellowish red472 ##STR219## yellowish red473 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellowish red474 H yellowish red__________________________________________________________________________475 ##STR220## H bluish red476 CH.sub.2CH.sub.2OH bluish red477 CH.sub.2CH.sub.2CH.sub.2OH bluish red478 ##STR221## bluish red479 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH bluish red480 CH.sub.2CH.sub.2OCH.sub.3 bluish red481 CH.sub.2CH.sub.2CH.sub.2OCH.sub.3 bluish red482 CH.sub.2CH.sub.2OCOCH.sub.3 bluish red__________________________________________________________________________483 ##STR222## H red484 CH.sub.2CH.sub.2OH red485 CH.sub.2CH.sub.2CH.sub.2OH red486 ##STR223## red487 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH red488 CH.sub.2CH.sub.2OCH.sub.3 red489 C.sub.2 H.sub.5 red__________________________________________________________________________490 ##STR224## CH.sub.2CH.sub.2OH red491 CH.sub.2CH.sub.2CH.sub.2OH red492 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH red__________________________________________________________________________493 ##STR225## CH.sub.2CH.sub.2OH red494 CH.sub.2CH.sub.2CH.sub.2OH red495 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH red__________________________________________________________________________496 ##STR226## CH.sub.2CH.sub.2OH red497 CH.sub.2CH.sub.2CH.sub.2OH red__________________________________________________________________________498 ##STR227## H red499 CH.sub.2CH.sub.2OH red500 CH.sub.2CH.sub.2CH.sub.2OH red501 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH red502 CH.sub.2CH.sub.2OCH.sub.3 red__________________________________________________________________________503 ##STR228## CH.sub.2CH.sub.2OH yellowish red504 CH.sub.2CH.sub.2CH.sub.2OH yellowish red505 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellowish red506 CH.sub.2CH.sub.2OCOCH.sub.3 yellowish red__________________________________________________________________________507 ##STR229## CH.sub.2CH.sub.2OH yellowish red508 CH.sub.2CH.sub.2CH.sub.2OH yellowish red509 ##STR230## yellowish red510 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellowish red__________________________________________________________________________511 ##STR231## CH.sub.2CH.sub.2OH yellowish red512 CH.sub.2CH.sub.2CH.sub.2OH yellowish red513 CH.sub.2CH.sub.2CH.sub.2OCH.sub.3 yellowish red__________________________________________________________________________514 ##STR232## CH.sub.2CH.sub.2OH red515 CH.sub.2CH.sub.2CH.sub.2OH bluish red516 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH bluish red517 CH.sub.2CH.sub.2CH.sub.2OCH.sub.2 bluish red__________________________________________________________________________518 ##STR233## CH.sub.2CH.sub.2OH red519 CH.sub.2CH.sub.2CH.sub.2OH red__________________________________________________________________________520 ##STR234## CH.sub.2CH.sub.2OH red521 CH.sub.2CH.sub.2CH.sub.2OH red522 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH red__________________________________________________________________________523 ##STR235## CH.sub.2CH.sub.2OH yellow524 CH.sub.2CH.sub.2CH.sub.2OH yellow525 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellow__________________________________________________________________________526 ##STR236## CH.sub.2CH.sub.2OH yellow527 CH.sub.2CH.sub.2CH.sub.2OH yellow528 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellow__________________________________________________________________________529 ##STR237## H red530 CH.sub.2CH.sub.2OH red531 CH.sub.2CH.sub.2CH.sub.2OH red532 ##STR238## red533 (CH.sub.2).sub.3O(CH.sub.2).sub.4OH red__________________________________________________________________________534 ##STR239## CH.sub.2CH.sub.2OH reddish blue535 CH.sub.2CH.sub.2CH.sub.2OH reddish blue536 ##STR240## reddish blue537 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH reddish blue__________________________________________________________________________ ##STR241## (CH.sub.2).sub.6OH reddish blue539 (CH.sub.2).sub.3O(CH.sub.2).sub.4OH reddish blue540 ##STR242## reddish blue__________________________________________________________________________541 ##STR243## CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH blue__________________________________________________________________________542 ##STR244## CH.sub.2CH.sub.2CH.sub.2OH yellowish brown543 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellowish brown__________________________________________________________________________544 ##STR245## CH.sub.2CH.sub.2CH.sub.2OH yellow545 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellow__________________________________________________________________________546 ##STR246## CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellow547 (CH.sub.2).sub.3OH yellow__________________________________________________________________________548 ##STR247## CH.sub.2CH.sub.2OH bluish red549 CH.sub.2CH.sub.2CH.sub.2OH bluish red550 H bluish red551 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH bluish red__________________________________________________________________________552 ##STR248## (CH.sub.2).sub.3OH bluish red553 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH bluish red554 H bluish red__________________________________________________________________________555 ##STR249## CH.sub.2CH.sub.2OH yellowish red__________________________________________________________________________556 ##STR250## CH.sub.2CH.sub.2CH.sub.2OH yellowish red557 CH.sub.2CH.sub.2OH yellowish red__________________________________________________________________________558 ##STR251## CH.sub.2CH.sub.2OH yellowish red__________________________________________________________________________559 ##STR252## H bluish red560 CH.sub.2CH.sub.2OH bluish red561 CH.sub.2CH.sub.2CH.sub.2OH bluish red562 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH bluish red563 (CH.sub.2).sub.3O(CH.sub.2).sub.4OH bluish red__________________________________________________________________________564 ##STR253## CH.sub.2CH.sub.2CH.sub.2OH violet565 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH violet566 H bluish red__________________________________________________________________________567 ##STR254## CH.sub.2CH.sub.2CH.sub.2OH violet568 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH violet__________________________________________________________________________569 ##STR255## CH.sub.2CH.sub.2CH.sub.2OH violet570 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH violet__________________________________________________________________________571 ##STR256## CH.sub.2CH.sub.2CH.sub.2OH red__________________________________________________________________________572 ##STR257## H orange573 CH.sub.2CH.sub.2OH orange574 CH.sub.2CH.sub.2CH.sub.2OH orange575 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH orange__________________________________________________________________________576 ##STR258## CH.sub.2CH.sub.2OH orange577 CH.sub.2CH.sub.2CH.sub. 2OH orange578 ##STR259## orange579 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH orange580 H orange__________________________________________________________________________581 ##STR260## CH.sub.2CH.sub.2OH violet582 CH.sub.2CH.sub.2CH.sub.2OH violet583 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH violet__________________________________________________________________________584 ##STR261## CH.sub.2CH.sub.2OH bluish red585 CH.sub.2CH.sub.2CH.sub.2OH bluish red586 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH bluish red587 ##STR262## bluish red__________________________________________________________________________588 ##STR263## CH.sub.2CH.sub.2OH bluish red589 CH.sub.2CH.sub.2CH.sub.2OH bluish red590 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH bluish red__________________________________________________________________________591 ##STR264## red__________________________________________________________________________592 ##STR265## CH.sub.2CH.sub.2OH bluish red593 CH.sub.2CH.sub.2CH.sub.2OH bluish red594 H bluish red__________________________________________________________________________595 ##STR266## CH.sub.2CH.sub.2OH violet596 CH.sub.2CH.sub.2CH.sub.2OH violet__________________________________________________________________________597 ##STR267## CH.sub.2CH.sub.2CH.sub.2OH reddish blue__________________________________________________________________________ TABLE 4__________________________________________________________________________Coupling component: ##STR268##__________________________________________________________________________Example Diazo component R.sup.1 Shade__________________________________________________________________________598 ##STR269## CH.sub.2CH.sub.2OH yellowish red599 CH.sub.2CH.sub.2CH.sub.2OH "600 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH "__________________________________________________________________________601 ##STR270## H yellowish red602 CH.sub.2CH.sub.2OH "603 CH.sub.2CH.sub.2OCOCH.sub.3 "604 CH.sub.2CH.sub.2CH.sub.2OH "605 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH "606 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2 OCHO "607 (CH.sub.2).sub.6 OH "__________________________________________________________________________608 ##STR271## CH.sub.2CH.sub.2CH.sub.2OH red609 CH.sub.2CH.sub.2OH "__________________________________________________________________________610 ##STR272## H red611 CH.sub.2CH.sub.2OH "612 CH.sub.2CH.sub.2CH.sub.2OH "613 ##STR273## "614 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH "__________________________________________________________________________615 ##STR274## CH.sub.2CH.sub.2OH red616 CH.sub.2CH.sub.2CH.sub.2OH "617 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH "618 (CH.sub.2).sub.3O(CH.sub.2).sub.4OH "__________________________________________________________________________619 ##STR275## CH.sub.2CH.sub.2CH.sub.2OH violet__________________________________________________________________________620 ##STR276## CH.sub.2CH.sub.2CH.sub.2OH red621 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH "__________________________________________________________________________622 ##STR277## CH.sub.2CH.sub.2CH.sub.2OH violet623 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH "__________________________________________________________________________624 ##STR278## CH.sub.2CH.sub.2CH.sub.2OH reddish blue625 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2 OH "__________________________________________________________________________626 ##STR279## CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH blue__________________________________________________________________________627 ##STR280## H red628 CH.sub.2CH.sub.2OH red629 CH.sub.2CH.sub.2CH.sub.2OH "630 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH "__________________________________________________________________________631 ##STR281## CH.sub.2CH.sub.2CH.sub.2OH bluish red632 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH "__________________________________________________________________________633 ##STR282## CH.sub.2CH.sub.2CH.sub.2OH bluish red634 CH.sub.2 CH.sub.2O(CH.sub.2).sub.2 OH "__________________________________________________________________________635 ##STR283## CH.sub.2CH.sub.2CH.sub.2OH red636 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH "__________________________________________________________________________ table 5__________________________________________________________________________coupling component ##STR284##__________________________________________________________________________Example Diazo component R.sup.2 Shade__________________________________________________________________________637 ##STR285## CH.sub.2CH.sub.2OCOCH.sub.3 red638 CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3 "639 CH.sub.2CH.sub.2CH.sub.2OH "640 CH.sub.2CH.sub.2OCH.sub.3 "__________________________________________________________________________641 ##STR286## CH.sub.2CH.sub.2OCOCH.sub.3 bluish red642 CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3 "643 CH.sub.2CH.sub.2CH.sub.2OH "644 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2 OCOCH.sub.3 "645 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH "646 CH.sub.2CH.sub.2OCH.sub.3 "__________________________________________________________________________647 ##STR287## CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3 red violet648 CH.sub.2CH.sub.2CH.sub.2OH "649 CH.sub.2CH.sub. 2OCH.sub.2CH.sub.2OCOCH.sub.3 "650 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH "651 CH.sub.2CH.sub.3 "652 CH.sub.2CH.sub.2CH.sub.2OCH.sub.3 "__________________________________________________________________________653 ##STR288## CH.sub.2CH.sub.2 OCOCH.sub.2COCH.sub.3 blue654 CH.sub.2CH.sub.2OCOCH.sub.3655 CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3 "656 CH.sub.2CH.sub.2CH.sub.2OH "657 CH.sub.2CH.sub.2OCH.sub.3 "658 CH.sub.2CH.sub.2CH.sub.2OC.sub.2 H.sub.5 "659 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCHO "660 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH "661 CH.sub.2CH.sub.OCH.sub.2CH.sub.2OCOCH.sub.3 "__________________________________________________________________________662 ##STR289## CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCOCH.sub.3 greenish blue__________________________________________________________________________ TABLE 6__________________________________________________________________________Coupling component: ##STR290##__________________________________________________________________________Example Diazo component R.sup.2 Shade__________________________________________________________________________663 ##STR291## H yellowish red664 CH.sub.2CH.sub.2OH red665 CH.sub.2CH.sub.2CH.sub.2OH red666 ##STR292## yellowish red667 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellowish red__________________________________________________________________________668 ##STR293## H yellowish red669 CH.sub.2CH.sub.2OH yellowish red670 CH.sub. 2CH.sub.2CH.sub.2OH yellowish red671 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellowish red__________________________________________________________________________672 ##STR294## H orange673 CH.sub.2CH.sub.2OH orange674 CH.sub.2CH.sub.2CH.sub.2OH orange675 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH orange__________________________________________________________________________676 ##STR295## H bluish red677 CH.sub.2CH.sub.2OH red678 CH.sub.2CH.sub.2CH.sub.2OH red__________________________________________________________________________679 ##STR296## H red680 CH.sub.2CH.sub.2OH red681 CH.sub.2CH.sub.2CH.sub.2OH red__________________________________________________________________________682 ##STR297## H yellow683 CH.sub.2CH.sub.2OH yellow__________________________________________________________________________

The further diazo components of Examples 345 to 662 give with the coupling components of the formula above Table 6 on page 46 dyes which have only negligible differences from the corresponding dyes with the 2-phenylpropylamine radical.

EXAMPLE 684

A mixture of 187 parts of 2,6-dichloro-3-cyano-4-methylpyridine, 150 parts of triethylamine, 200 parts of isopropanol and 160 parts of 2-amino-6-methylheptanol-(6) is stirred for eight hours at about 55.degree. to 80.degree. C. The mixture is then allowed to cool and is poured with stirring into about 1500 parts of water, 200 parts of concentrated hydrochloric acid and 200 parts of ice. The whole is further stirred for another hour, the oil of the probable formula: ##STR298## which separates is decanted and washed with water. The oil contains a minor amount of 2-chloro-3-cyano-4-methyl-6-aminoheptanolpyridine isomer.

15 parts of the oil is stirred with 40 parts of .beta.-hydroxy-ethylamine for 6 hours at 145.degree.-160.degree. C, allowed to cool, mixed with 100 parts of water and acidified with hydrochloric acid to a pH of about 0 to 1. After any necessary addition of some glacial acetic acid or dimethylformamide, a solution of the coupling component of the probable formula: ##STR299## is obtained which contains a minor amount of the 2,6-dialkylamino isomer.

The solution of this coupling is cooled to 0 to 3.degree. C by adding ice and a diazonium salt solution is added which has been obtained as follows: 6.9 parts of p-nitroaniline has added to it about 30 parts of concentrated hydrochloric acid (30%) and 80 parts of water, then the mixture is cooled to 0.degree. C and 15 parts by volume of 23% sodium nitrate solution is added in portions. Stirring is continued for another two hours, any excess of nitrous acid present is removed as usual and filtration carried out.

The filtrate is added to the coupling mixture; then such an amount of sodium acetate or caustic soda solution is gradually added while stirring that the pH of the coupling mixture is from about 2 to 3. If the mixture is difficult to stir, ice-water may be added. When coupling is over the mixture is heated to 70.degree. to 80.degree. C, filtered, and the residue washed with water and dried. About 20 parts of a brown powder is obtained which probably has the formula: ##STR300## (the dye contains a minor proportion of the 2,6-dialkylaminopyridine isomer). It dissolves in dimethylformamide with an orange color and dyes polyethylene terephthalate cloth full, clear orange shades having outstanding fastness properties.

The following dyes characterized by the diazo and coupling components are obtained analogously to the methods described.

TABLE 1__________________________________________________________________________Coupling component: ##STR301##Example Dizo component R.sup.2 Shade__________________________________________________________________________685 ##STR302## H yellow686 CH.sub.2CH.sub.2OH yellow687 CH.sub.2CH.sub.2CH.sub.2OH yellow688 ##STR303## yellow__________________________________________________________________________689 ##STR304## H yellow690 CH.sub.2CH.sub.2 OH yellow691 CH.sub.2CH.sub.2CH.sub.2OH yellow692 ##STR305## yellow693 ##STR306## yellow__________________________________________________________________________694 ##STR307## H yellow695 CH.sub.2CH.sub.2OH yellow696 CH.sub.2CH.sub.2CH.sub.2OH yellow697 ##STR308## yellow698 ##STR309##699 ##STR310## H yellow700 CH.sub.2CH.sub.2OH yellow701 CH.sub.2CH.sub.2CH.sub.2OH yellow702 ##STR311## yellow703 ##STR312## yellow__________________________________________________________________________704 ##STR313## H orange705 CH.sub.2CH.sub.2OH orange706 CH.sub.2CH.sub.2OH orange707 ##STR314## orange__________________________________________________________________________708 ##STR315## H oange709 CH.sub.2CHOH oragne710 CH.sub.2CH.sub.2OH orange__________________________________________________________________________711 ##STR316## H orange712 ##STR317## orange713 CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3 orange714 ##STR318## orange715 (CH.sub.2).sub.5 COOCH.sub.3 orange716 CH.sub.2CH.sub.2OCH.sub.3 orange717 CH.sub.2CH.sub.2CH.sub.2OCH.sub.3 orange718 CH.sub.2CH.sub.2 OCHO orange719 (CH.sub.2).sub.6OH orange__________________________________________________________________________720 ##STR319## H yellowish red721 CH.sub.2CH.sub.2OH yellowish red722 CH.sub.2CH.sub.2CH.sub.2OH yellowish red723 ##STR320## yellowishred724 CH.sub.2CH.sub.2CH.sub.2OCH.sub.3 yellowish red__________________________________________________________________________725 ##STR321## CH.sub.2CH.sub.2OH yellowish red726 CH.sub.2CH.sub.2CH.sub.2OH yellowish red__________________________________________________________________________727 ##STR322## CH.sub.2CH.sub.2OH yellowish red728 CH.sub.2CH.sub.2CH.sub.2OH yellowish red__________________________________________________________________________729 ##STR323## CH.sub.2CH.sub.2OH orange730 CH.sub.2CH.sub.2CH.sub.2OH orange__________________________________________________________________________731 ##STR324## CH.sub.2CH.sub.2OH yellow732 CH.sub.2CH.sub.2CH.sub.2OH yellow__________________________________________________________________________733 ##STR325## CH.sub.2CH.sub.2OH orange734 CH.sub.2CH.sub.2CH.sub.2OH orange__________________________________________________________________________735 ##STR326## CH.sub.2CH.sub.2OH yellow736 CH.sub.2CH.sub.2CH.sub.2OH yellow__________________________________________________________________________737 ##STR327## H yellow738 CH.sub.2CH.sub.2OH yellow739 CH.sub.2CH.sub.2CH.sub.2OH yellow__________________________________________________________________________740 CH.sub.2CH.sub.2CH.sub.2OCH.sub.3741 ##STR328## CH.sub.2CHk.sub.2OH yellow742 CH.sub.2CH.sub.2CH.sub.2OH yellow__________________________________________________________________________743 ##STR329## H yellow744 CH.sub.2CH.sub.2OH yellow745 CH.sub.2CH.sub.2 OH yellow746 (CH.sub.2).sub.5 COCH yellow (polyamide)747 CH.sub.2CH.sub.2OCH.sub.3 yellow__________________________________________________________________________748 ##STR330## CH.sub.2CH.sub.2CH.sub.2OH yellowish red749 CH.sub.2CH.sub.2OH yellowish red__________________________________________________________________________750 ##STR331## CH.sub.2CH.sub.2CH.sub.2OH orange__________________________________________________________________________751 ##STR332##752 CH.sub.2CH.sub.2CH.sub.2OH yellow__________________________________________________________________________753 ##STR333## CH.sub.2CH.sub.2OH yellow754 CH.sub.2CH.sub.2CH.sub.2 OH yellow755 ##STR334## yellow__________________________________________________________________________756 ##STR335## CH.sub.2CH.sub.2OH yellow757 ##STR336## CH.sub.2CH.sub.2OH yellow758 CH.sub.2CH.sub.2CH.sub.2OH yellow (CH.sub.2).sub.5 COOH yellow (polyamide)__________________________________________________________________________759 ##STR337## CH.sub.2CH.sub.2OH yellow760 CH.sub.2CH.sub.2CH.sub.2OH yellow__________________________________________________________________________761 ##STR338## CH.sub.2CH.sub.2OH yellow762 CH.sub.2CH.sub.2CH.sub.2OH yellow__________________________________________________________________________ TABLE 2__________________________________________________________________________Coupling component: ##STR339##__________________________________________________________________________Example Diazo component R.sup.1 Shade__________________________________________________________________________763 ##STR340## CH.sub.2CH.sub.2OH yellow764 CH.sub.2CH.sub.2CH.sub.2OH yellow__________________________________________________________________________765 ##STR341## H yellow766 CH.sub.2CH.sub.2OH yellow767 CH.sub.2CH.sub.2CH.sub.2OH yellow__________________________________________________________________________768 ##STR342## CH.sub.2CH.sub.2OH yellow__________________________________________________________________________769 ##STR343## CH.sub.2CH.sub.2OH orange770 CH.sub.2CH.sub.2CH.sub.2OH orange__________________________________________________________________________771 ##STR344## CH.sub.2CH.sub.2CH.sub.2OH orange__________________________________________________________________________772 ##STR345## CH.sub.2CH.sub.2OH yellowish red773 CH.sub.2CH.sub. 2CH.sub. 2OH yellowish red__________________________________________________________________________774 ##STR346## CH.sub. 2CH.sub.2CH.sub. 2OH yellow__________________________________________________________________________775 ##STR347## CH.sub.2CH.sub.2OH yellow776 CH.sub. 2CH.sub.2CH.sub. 2OH yellow777 CH.sub.2CH.sub.2CH.sub.2CH.sub.3 yellow__________________________________________________________________________

EXAMPLE 778

19.5 parts of 3-amino-5-nitro-2,1-benzoisothiazole is added in portions while stirring at 15.degree. to 25.degree. C to about 75 to 85 parts of 96% sulfuric acid and the mixture is then cooled to 0.degree. to 4.degree. C. Then 32.5 parts of 23% nitrosylsulfuric acid is dripped in at this temperature. Diazotization is ended after stirring for from about three to four hours at 0.degree. to 5.degree. C. The diazonium salt mixture is then added to a solution or suspension, cooled to 0.degree. C, of 34.9 parts of the coupling component of the formula: ##STR348## in 50 parts of 30% hydrochloric acid, 500 parts of water and 150 parts of glacial acetic acid. During coupling, ice and sodium acetate are added at intervals so that the temperature of the coupling mixture does not rise above 5.degree. C and the pH is finally about 2. The precipitated dye of the formula: ##STR349## is filtered off, washed with hot water and dried. About 53.6 parts of a black powder is obtained which dissolves in dimethylformamide with a reddish blue color.

EXAMPLE 779

21.6 parts of 2-amino-5-nitrobenzenemethylsulfone-(1) is stirred at from 10.degree. to 15.degree. C in 100 parts of 96% sulfuric acid. Then 32.5 parts of 23% nitrosylsulfuric acid is added at 0.degree. to 5.degree. C and the mixture is stirred for four hours at 5.degree. to 10.degree. C. The diazonium salt solution obtained is allowed to flow within about twenty minutes into 35.5 parts of a suspension, cooled to 0.degree. C, of the coupling component of the formula: ##STR350## in a mixture of 100 parts of glacial acetic acid, 1 part of sulamic acid, 30 parts by volume of concentrated hydrochloric acid and 500 parts of water. During coupling the mixture is kept at pH 0 to 2 by adding sodium acetate, and water and ice are added for better stirring.

After coupling has ended (having proceeded at above pH 2) the dye mixture of the formulae: ##STR351## is suction filtered, washed with water and dried. A dark powder is obtained which dissolves in dimethylformamide with a reddish violet color and dyes polyethylene terephthalate cloth reddish violet shades.

TABLE 3__________________________________________________________________________Coupling component:__________________________________________________________________________ ##STR352##__________________________________________________________________________Example Diazo component R.sup.2 Shade__________________________________________________________________________780 ##STR353## CH.sub.2CH.sub.2OH yellowish red781 CH.sub.2CH.sub.2CH.sub.2OH yellowish red782 ##STR354## yellowish red783 CH.sub.2CH.sub.2CH.sub.2OCHO yellowish red784 H yellowish red785 (CH.sub.2).sub.6OH yellowish red786 CH.sub.2CH.sub.2OCOCH.sub.3 yellowish__________________________________________________________________________ red787 ##STR355## CH.sub.2CH.sub.2OH yellowish red788 CH.sub.2CH hd 2CH.sub.2OH yellowish red789 ##STR356## yellowish red790 H yellowish__________________________________________________________________________ red791 ##STR357## H red792 CH.sub.2CH.sub.2OH red793 CH.sub.2CH hd 2CH.sub.2OH red794 ##STR358## red795 CH.sub.2CH.sub.2OCH.sub.3 red796 CH.sub.2CH.sub.2CH.sub.2OCH.sub.3 red797 CH.sub.2CH.sub.2OCOCH.sub.3 red__________________________________________________________________________798 ##STR359## H red799 CH.sub.2CH.sub.2OH red800 CH.sub.2CH.sub.2CH.sub.2OH red801 ##STR360## red__________________________________________________________________________802 ##STR361## CH.sub.2CH.sub.2OCH.sub.3 red803 C.sub.2 H.sub.5 red__________________________________________________________________________804 ##STR362## CH.sub.2CH.sub.2OH red805 CH.sub.2CH.sub.2CH.sub.2OH red__________________________________________________________________________806 ##STR363## CH.sub.2CH.sub.2OH red807 CH.sub.2CH.sub.2CH.sub.2OH red__________________________________________________________________________808 ##STR364## CH.sub.2CH.sub.2OH red809 CH.sub.2CH.sub.2CH.sub.2OH red__________________________________________________________________________810 ##STR365## H red811 CH.sub.2CH.sub.2OH red812 CH.sub.2CH.sub.2CH.sub.2OH red813 CH.sub.2CH.sub.2OCH.sub.3 red__________________________________________________________________________814 ##STR366## CH.sub.2CH.sub.2OH yellowish red815 CH.sub.2CH.sub.2CH.sub.2OH yellowish red816 CH.sub.2CH.sub.2OCOCH.sub.3 yellowish__________________________________________________________________________ red817 ##STR367## CH.sub.2CH.sub.2CH.sub.2OH yellowish red818 CH.sub.2CH.sub.2CH.sub.2OH yellowish__________________________________________________________________________ red819 ##STR368## yellowish__________________________________________________________________________ red820 ##STR369## CH.sub.2CH.sub.2OH yellowish red821 CH.sub.2CH.sub.2CH.sub.2OH yellowish red822 CH.sub.2CH.sub.2CH.sub.2OCH hd yellowish__________________________________________________________________________ red823 ##STR370## CH.sub.2CH.sub.2OH bluish red864 CH.sub.2CH.sub.2CH.sub.2OH orange__________________________________________________________________________865 ##STR371## CH.sub.2CH.sub.2OH orange866 CH.sub.2CH.sub.2CH.sub.2OH orange867 ##STR372## orange868 H orange__________________________________________________________________________869 ##STR373## CH.sub.2CH.sub.2OH violet870 CH.sub.2CH.sub.2CH.sub.2OCH.sub.3 violet__________________________________________________________________________871 ##STR374## CH.sub.2CH.sub.2OH bluish red872 CH.sub.2CH.sub.2CH.sub.2OH bluis red873 ##STR375## bluish red__________________________________________________________________________874 ##STR376## CH.sub.2CH.sub.2OH bluish red875 CH.sub.2CH.sub.2CH.sub. 2OH bluish red__________________________________________________________________________876 ##STR377## CH.sub.2CH.sub.2CH.sub.2OH yellowish__________________________________________________________________________ red877 ##STR378## CH.sub.2CH.sub.2OH bluish red878 CH.sub.2CH.sub.2CH.sub.2OH bluish red879 H bluish red__________________________________________________________________________880 ##STR379## CH.sub.2CH.sub.2OH violet881 CH.sub.2CH.sub.2CH.sub.2OH violet__________________________________________________________________________882 ##STR380## CH.sub.2CH.sub.2CH.sub.2OH blue__________________________________________________________________________ TABLE 4__________________________________________________________________________ ##STR381##Coupling component:Example Diazo component R.sup.1 Shade__________________________________________________________________________883 ##STR382## CH.sub.2CH.sub.2OH yellowish red884 CH.sub.2CH.sub.2CH.sub.2OH "__________________________________________________________________________885 ##STR383## H yellowish red886 CH.sub.2CH.sub.2OH "887 CH.sub.2CH.sub.2OCOCH.sub.3 "888 CH.sub.2CH.sub.2CH.sub.2OH "889 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCHO "890 (CH.sub.2).sub.6 OH "__________________________________________________________________________891 ##STR384## CH.sub.2CH.sub.2CH.sub.2OH red892 CH.sub.2CH.sub.2OH "__________________________________________________________________________893 ##STR385## H red894 CH.sub.2CH.sub.2OH "895 CH.sub.2CH.sub.2CH.sub.2OH "__________________________________________________________________________896 ##STR386## H red897 CH.sub.2CH.sub.2OH "898 CH.sub.2CH.sub.2CH.sub.2OH "__________________________________________________________________________899 ##STR387## CH.sub.2CH.sub.2CH.sub.2OH violet__________________________________________________________________________900 ##STR388## CH.sub.2CH.sub. 2CH.sub.2OH red__________________________________________________________________________901 ##STR389## CH.sub.2CH.sub.2CH.sub.2OH violet__________________________________________________________________________902 ##STR390## CH.sub.2CH.sub.2CH.sub.2OH reddish blue__________________________________________________________________________903 ##STR391## H red904 CH.sub.2CH.sub.2OH "905 CH.sub.2CH.sub.2CH.sub.2OH "__________________________________________________________________________906 ##STR392## CH.sub.2CH.sub.2CH.sub.2OH bluish red__________________________________________________________________________907 ##STR393## CH.sub.2CH.sub.2CH.sub.2OH bluish red__________________________________________________________________________908 ##STR394## CH.sub.2CH.sub.2CH.sub.2OH red__________________________________________________________________________ TABLE 5__________________________________________________________________________ ##STR395##Coupling component:Example Diazo component R.sup.2 Shade__________________________________________________________________________909 ##STR396## CH.sub.2CH.sub.2OH red910 CH.sub.2CH.sub.2CH.sub.2OCH.sub.3 "911 CH.sub.2CH.sub.2CH.sub.2OH "912 CH.sub.2CH.sub.2OCH.sub.3 "__________________________________________________________________________913 ##STR397## CH.sub.2CH.sub.2OH bluish red914 CH.sub.2CH.sub.2CH.sub.2OH "915 CH.sub.2CH.sub.2C.sub.6 H.sub.5 "916 CH.sub.2CH.sub.2CH.sub.2OCH.sub.3 "917 C.sub.2 H.sub.5 "918 ##STR398## CH.sub.2CH.sub.2OH red violet919 (CH.sub.2).sub.3OH "920 C.sub.2 H.sub.4 OCH.sub.3 "921 C.sub.2 H.sub.5 "__________________________________________________________________________922 ##STR399## CH.sub.2CH.sub.2OH red violet923 (CH.sub.2).sub.3OH "924 C.sub.2 H.sub.5 "__________________________________________________________________________925 ##STR400## (CH.sub.2).sub.3OH blue926 C.sub.3 H.sub.6OCH.sub.3 "__________________________________________________________________________927 ##STR401## (CH.sub.2).sub.3OH yellowish red928 CH.sub.2CH.sub.2CH.sub.2OCH.sub.3 "929 C.sub.3 H.sub.7 (n) "__________________________________________________________________________930 ##STR402## CH.sub.2CH.sub.2OH yellowish red931 (CH.sub.2).sub.3OH "932 C.sub.6 H.sub.5 red__________________________________________________________________________933 ##STR403## CH.sub.2CH.sub.2OH orange934 CH.sub.2CH.sub.2CH.sub.2OH "__________________________________________________________________________ table 6__________________________________________________________________________ ##STR404##coupling component:Example Diazo component R.sup.2 Shade__________________________________________________________________________935 ##STR405## CH.sub.2CH.sub.2C.sub.6 H.sub.5 yellowish red936 CH.sub.2CH.sub.2OH red937 CH.sub.2CH.sub.2CH.sub.2OH "938 ##STR406## yellowish red939 ##STR407## CH.sub.2CH.sub.2C.sub.6 H.sub.5 yellowish red940 CH.sub.2CH.sub.2OH "941 CH.sub.2CH.sub.2CH.sub.2OH "__________________________________________________________________________942 ##STR408## CH.sub.2CH.sub.2C.sub.6 H.sub.5 orange943 CH.sub.2CH.sub.2OH "944 CH.sub.2CH.sub.2CH.sub.2OH "__________________________________________________________________________945 ##STR409## C.sub.4 H.sub.9 (n) bluish red946 CH.sub.2CH.sub.2OH red947 CH.sub.2CH.sub.2CH.sub.2OH "__________________________________________________________________________948 ##STR410## C.sub.4 H.sub.9 (n) red949 CH.sub.2CH.sub.2OH "950 CH.sub.2CH.sub.2CH.sub.2OH "__________________________________________________________________________951 ##STR411## CH.sub.2CH.sub.2C.sub.6 H.sub.5 yellow952 CH.sub.2CH.sub.2OH "__________________________________________________________________________

example 953

20 parts of the dye of the formula: ##STR412## is stirred with 100 parts of formic acid for ten hours at 80.degree. to 100.degree. C. About 50 parts of formic acid is then distilled off at subatmospheric pressure and the residue is cooled and iluted with 500 parts by volume of water. The precipitated dye of the formula: ##STR413## is filtered off, washed with water and dried. It dissolves in dimethylformamide with an orange color and dyes polyethylene terephthalate cloth full orange shades of excellent light fastness.

The following dyes are also valuable:

__________________________________________________________________________954 ##STR414## orange__________________________________________________________________________955 ##STR415## yellowish red__________________________________________________________________________956 ##STR416## yellow__________________________________________________________________________957 ##STR417## orange__________________________________________________________________________958 ##STR418## reddish violet__________________________________________________________________________959 ##STR419## yellow__________________________________________________________________________960 ##STR420## yellowish red__________________________________________________________________________961 ##STR421## yellow__________________________________________________________________________

EXAMPLE 962

A mixture of 56 parts of 2,6-dichloro-3-cyano-4-methylpyridine, 160 parts by volume of N-methylpyrrolidone and 50 parts by volume of triethylamine has 50 parts of the amine of the formula: ##STR422## added to it. The mixture is stirred for about ten hours at 55.degree. to 60.degree. C, then about 1000 parts of water is added and the mixture is acidified with concentrated hydrochloric acid. A red brown oil separates and is isolated after decantation of the aqueous phase and washing with water. About 60 parts of 2-hydroxyethylamine is then added and the mixture is stirred for from three to four hours at 105.degree. to 130.degree. C. After cooling the whole is diluted with about 300 parts of glacial acetic acid and acidified with 50 parts by volume of concentrated hydrochloric acid. Ice is added to the mixture until it has been cooled to 0.degree. C and then there is added a diazonium salt solution which has been prepared as follows: 49 parts of 2-amino-5-nitrobenzonitrile is added at 0.degree. at 4.degree. C in portions while stirring well to a mixture of 240 parts of concentrated sulfuric acid and 98 parts of 23% nitrosylsulfuric acid. The mixture is stirred for from four to five hours at 0.degree. to 4.degree. C and is then added in portions to the coupling mixture described above. The mixture is kept stirrable and the temperature is kept at not more than 0.degree. C by the simultaneous addition of ice and ice-water. Aqueous sodium acetate solution is then added over twenty minutes until the pH of the coupling mixture is from 1.5 to 1.0. After coupling is over the mixture is heated to 60.degree. to 80.degree. C, and the precipitated dye is suction filtered, washed with water and dried. About 152 parts of a reddish brown powder is obtained which dissolves in dimethylformamide with a red color and dyes polyethylene terephthalate cloth red shades of excellent fastness to light, wet treatment and dry-heat pleating and setting.

The dye has the formula: ##STR423## and contains a minor amount of the 2,6-dialkylaminopyridine isomer of the formula: ##STR424##

Dyes characterized in the following Tables by specifying the diazo and coupling components are obtained analogously:

TABLE 1__________________________________________________________________________ ##STR425##Coupling component:Example Diazo component R.sup.2 Shade__________________________________________________________________________963 ##STR426## H yellow964 CH.sub.2CH.sub.2OH "965 CH.sub.2CH.sub.2OH "966 CH.sub.2CHOH " CH.sub.3967 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH "968 CH.sub.2CH.sub.2OCH.sub.3 "969 ##STR427## H yellow970 CH.sub.2CH.sub.2OH "971 CH.sub.2CH.sub.2CH.sub.2OH "972 ##STR428## "973 CH.sub.2CH.sub.2OCH.sub.2OH "974 ##STR429## H "975 CH.sub.2CH.sub.2CH "976 CH.sub.2CH.sub.2CH.sub.2OH "977 ##STR430## "978 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH "979 ##STR431## H "980 CH.sub.2CH.sub.2OH "981 CH.sub.2CH.sub.2CH.sub.2OH "982 ##STR432## "982 a) CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH "983 ##STR433## H orange984 CH.sub.2CH.sub.2OH985 CH.sub.2CH.sub.2CH.sub.2OH986 ##STR434##987 CH.sub.2CH.sub.2 OCH.sub.2CH.sub.2OH988 ##STR435## H orange989 CH.sub.2CH.sub.2OH990 CH.sub.2CH.sub.2CH.sub.2OH991 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH992 ##STR436## H orange993 CH.sub.2CH.sub.2OH994 CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.3995 ##STR437##996 ##STR438## CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH orange997 CH.sub.2CH.sub.2OCH.sub.3998 CH.sub.2CH.sub.2CH.sub.2OCH.sub.3999 CH.sub.2CH.sub.2 OCHO1000 (CH.sub.2).sub.6OH1001 ##STR439## H yellowish red1002 CH.sub.2CH.sub.2OH1003 CH.sub.2CH.sub.2CH.sub.2OH1004 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH1005 ##STR440##1006 CH.sub.2CH.sub.2CH.sub.2OCH.sub.31007 CH.sub.2CH.sub.2CH.sub.2OCOCH.sub.31008 ##STR441## CH.sub.2CH.sub.2OH yellowish red1009 CH.sub.2CH.sub.2CH.sub.2OH1010 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH1011 ##STR442## CH.sub.2CH.sub.2OH yellowish red1012 CH.sub.2CH.sub.2CH.sub.2OH1013 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH1014 ##STR443## CH.sub.2CH.sub.2OH orange1015 CH.sub.2CH.sub.2CH.sub.2OH1016 ##STR444## CH.sub.2CH.sub.2OH yellow1017 CH.sub.2CH.sub.2CH.sub.2OH1018 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH1019 ##STR445## CH.sub.2CH.sub.2OH orange1020 CH.sub.2CH.sub.2CH.sub.2OH1021 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH1022 ##STR446## CH.sub.2CH.sub.2OH yellow1023 CH.sub.2CH.sub.2CH.sub.2OH1024 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH1025 ##STR447## H yellow1026 CH.sub.2CH.sub.2OH1027 CH.sub.2CH.sub.2CH.sub.2OH1028 CH.sub.2CH.sub.2CH.sub.2OCH.sub.31029 ##STR448## CH.sub.2CH.sub.2OH yellow1030 CH.sub.2CH.sub.2CH.sub.2OH1031 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH1032 ##STR449## H yellow1033 CH.sub.2CH.sub.2OH1034 CH.sub.2CH.sub.2CH.sub.2OH1035 CH.sub.2CH.sub.2OCH.sub.2OH1036 CH.sub.2CH.sub.2OCH.sub.31037 ##STR450## CH.sub.2CH.sub.2CH.sub.2OH yellowish red1038 CH.sub.2CH.sub.2OH1039 ##STR451## CH.sub.2CH.sub.2CH.sub.2OH orange1040 CH.sub.2CH.sub.2OCH.sub.2CH.sub. 2OH1041 ##STR452## CH.sub.2CH.sub.2OH yellow1042 CH.sub.2CH.sub.2CH.sub.2OH1043 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH1044 ##STR453## CH.sub.2CH.sub.2OH yellow1045 CH.sub.2CH.sub.2CH.sub.2OH1046 ##STR454##1047 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH1048 ##STR455## CH.sub.2CH.sub.2OH yellow1049 CH.sub.2CH.sub.2CH.sub.2OH1050 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH1051 ##STR456## CH.sub. 2CH.sub.2OH yellow1052 CH.sub.2CH.sub.2CH.sub.2OH1053 ##STR457## CH.sub.2CH.sub.2OH yellow1054 CH.sub.2CH.sub.2CH.sub.2OH__________________________________________________________________________ table 2__________________________________________________________________________ ##STR458##coupling componentExample Diazo component R.sup.1 Shade__________________________________________________________________________1055 ##STR459## CH.sub.2CH.sub.2OH yellow1056 CH.sub.2CH.sub.2CH.sub. 2OH__________________________________________________________________________1057 ##STR460## H yellow1058 CH.sub.2CH.sub.2OH1059 CH.sub.2CH.sub.2CH.sub.2OH1060 CH.sub.2CH.sub.2CH.sub.2O(CH.sub.2).sub.2 OH__________________________________________________________________________1061 ##STR461## CH.sub.2CH.sub.2OH yellow1062 CH.sub.2CH.sub.2CH.sub.2OH1063 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH__________________________________________________________________________1064 ##STR462## CH.sub.2CH.sub.2OH orange1065 CH.sub.2CH.sub.2CH.sub.2OH1066 CH.sub.2CH.sub.2O(CH.sub.2).sub.2 OH__________________________________________________________________________1067 ##STR463## CH.sub.2CH.sub.2CH.sub.2OH orange1068 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH__________________________________________________________________________1069 ##STR464## CH.sub.2CH.sub.2OH scarlet1070 CH.sub.2CH.sub.2CH.sub.2OH__________________________________________________________________________1071 ##STR465## CH.sub.2CH.sub.2CH.sub.2OH yellow1072 CH.sub.2CH.sub.2O(CH.sub.2).sub.2 OH__________________________________________________________________________1073 ##STR466## CH.sub.2CH.sub.2OH yellow1074 CH.sub.2CH.sub.2CH.sub.2OH1075 CH.sub.2CH.sub.2CH.sub.2CH.sub.3__________________________________________________________________________

example 1076

19.5 parts of 3-amino-5-nitro-2,1-benzoisothazole is added while stirring at 15.degree. to 25.degree. C in portions to about 75 to 85 parts of 96% sulfuric acid and the mixture is cooled to 0.degree. to 4.degree. C. 32.5 parts of 23% nitrosylsulfuric acid is then dripped in at this temperature. Diazotization is over after from about three to four hours' stirring at 0.degree. to 5.degree. C. The diazonium salt mixture is added to a solution or suspension of 34 parts of the coupling component of the formula: ##STR467## in 50 parts of 30% hydrochloric acid, 500 parts of water and 150 parts of glacial acetic acid. During coupling ice and sodium acetate are added at intervals so that the temperature of the coupling mixture does not rise above 5.degree. C and the pH is finally about 2. The precipitated dye of the formula: ##STR468## is filtered off, washed with hot water and dried. About 33 parts of a black powder is obtained which dissolves in dimethylformamide with a reddish blue color and dyes polyethylene terephthalate cloth reddish blue shades having very good fastness properties.

EXAMPLE 1077

11 parts of 2-amino-5-nitrobenzoic acid methoxyethyl ester has 180 parts by volume of glacial acetic acid, 15 parts by volume of concentrated hydrochloric acid and 10 parts of ice added to it. The whole is cooled to 0.degree. to 5.degree. C and then 13.5 parts by volume of 23% sodium nitrite solution is added. After stirring for from about two to three hours any excess of nitrous acid present is destroyed in the usual way, the diazonium salt solution is diluted with 1000 party by volume of ice-water and then a solution of 11.9 parts of the coupling component of the formula: ##STR469## in 100 parts of glacial acetic acid and 10 parts of concentrated hydrochloric acid is added. The whole is stirred for half an hour and then 50% caustic soda solution is adde until the pH of the coupling mixture is 2. After coupling is over the precipitated dye of the formula: ##STR470## is filtered off, washed with water and dried.

A red powder is obtained which dissolves in dimethylformamide with a red color and dyes polyethylene terephthalate full yellowish red shades having very good fastness properties.

TABLE 3__________________________________________________________________________ ##STR471##Coupling component:Example Diazo component R.sup.2 Shade__________________________________________________________________________1078 ##STR472## CH.sub.2CH.sub.31079 CH.sub.2CH.sub.2CH.sub.2OH1080 ##STR473##1081 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH1082 CH.sub.2CH.sub.2CH.sub.2OCH.sub.31083 H1084 (CH.sub.2).sub.6OH1085 CH.sub.2CH.sub.2OCOCH.sub.3__________________________________________________________________________1086 ##STR474## CH.sub.2CH.sub.2OH1087 CH.sub.2CH.sub.2CH.sub.2OH1088 ##STR475##1089 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH1090 H__________________________________________________________________________1091 ##STR476## H1092 CH.sub.2CH.sub.2OH1093 CH.sub.2CH.sub.2CH.sub.2OH1094 ##STR477##1095 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH1096 CH.sub.2CH.sub.2OCH.sub.31097 CH.sub.2CH.sub.2CH.sub.2OCH.sub.31098 CH.sub.2CH.sub.2OCOCH.sub.3__________________________________________________________________________1099 ##STR478## H red1100 CH.sub.2CH.sub.2OH1101 CH.sub.2CH.sub.2CH.sub.2OH1102 ##STR479##1103 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH1104 CH.sub.2CH.sub.2OCH.sub.31105 C.sub.2 H.sub.5__________________________________________________________________________1106 ##STR480## CH.sub.2CH.sub.2OH red1107 CH.sub.2CH.sub.2CH.sub.2OH1108 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH__________________________________________________________________________1109 ##STR481## CH.sub.2CH.sub.2OH red1110 CH.sub.2CH.sub.2CH.sub.2OH1111 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH__________________________________________________________________________1112 ##STR482## CH.sub.2CH.sub.2OH red1113 CH.sub.2CH.sub.2CH.sub.2OH__________________________________________________________________________1114 ##STR483## H red1115 CH.sub.2CH.sub.2OH1116 CH.sub.2CH.sub.2CH.sub.2OH1117 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH1118 CH.sub.2CH.sub.2OCH.sub.3__________________________________________________________________________1119 ##STR484## CH.sub.2CH.sub.2OH yellowish red1120 CH.sub.2CH.sub.2CH.sub.2OH1121 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH1122 CH.sub.2CH.sub.2OCH.sub.3__________________________________________________________________________1123 ##STR485## CH.sub.2CH.sub.2OH yellowish red1124 CH.sub.2CH.sub.2CH.sub.2OH1125 ##STR486##1126 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH__________________________________________________________________________1127 ##STR487## CH.sub.2CH.sub.2OH yellowish red1128 CH.sub.2CH.sub.2CH.sub.2OH1129 CH.sub.2CH.sub.2CH.sub.2OCH.sub.3__________________________________________________________________________1130 ##STR488## CH.sub.2CH.sub.2OH bluish red1131 CH.sub.2CH.sub.2CH.sub.2OH1132 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH1133 CH.sub.2CH.sub.2CH.sub.2OCH.sub.3__________________________________________________________________________1134 ##STR489## CH.sub.2CH.sub.2OH red1135 CH.sub.2CH.sub.2CH.sub.2OH__________________________________________________________________________1136 ##STR490## CH.sub.2CH.sub.2OH red1137 CH.sub.2CH.sub.2CH.sub.2OH1138 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH__________________________________________________________________________1139 ##STR491## CH.sub.2CH.sub.2OH yellow1140 CH.sub.2CH.sub.2CH.sub.2OH1141 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH__________________________________________________________________________1142 ##STR492## CH.sub.2CH.sub.2OH yellow1143 CH.sub.2CH.sub.2CH.sub.2OH1144 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH__________________________________________________________________________1145 ##STR493## H red1146 CH.sub.2CH.sub.2OH1147 CH.sub.2CH.sub.2CH.sub.2OH1148 ##STR494##1149 (CH.sub.2).sub.3O(CH.sub.2).sub.4OH__________________________________________________________________________1150 ##STR495## CH.sub.2CH.sub.2OH reddish blue1151 CH.sub.2CH.sub.2CH.sub.2OH1152 ##STR496##1153 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH1154 (CH.sub.2).sub.6OH1155 (CH.sub.2).sub.3O(CH.sub.2).sub.4OH1156 ##STR497##__________________________________________________________________________1157 ##STR498## CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH blue__________________________________________________________________________1158 ##STR499## CH.sub.2CH.sub.2CH.sub.2OH yellowish brown1159 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH__________________________________________________________________________1160 ##STR500## CH.sub.2CH.sub.2CH.sub.2OH yellow1161 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH__________________________________________________________________________1162 ##STR501## CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH yellow1163 (CH.sub.2).sub.3OH__________________________________________________________________________1164 ##STR502## CH.sub.2CH.sub.2OH bluish red1165 CH.sub.2CH.sub.2CH.sub.2OH1166 H1167 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH__________________________________________________________________________1168 ##STR503## (CH.sub.2).sub.3 3OH bluish red1169 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH1170 H__________________________________________________________________________1171 ##STR504## CH.sub.2CH.sub.2OH yellowish__________________________________________________________________________ red1172 ##STR505## CH.sub.2CH.sub.2CH.sub.2OH scarlet1173 CH.sub.2CH.sub.2OH__________________________________________________________________________1174 ##STR506## CH.sub.2CH.sub.2OH scarlet1175 ##STR507## H bluish red1176 CH.sub.2CH.sub.2OH1177 CH.sub.2CH.sub.2CH.sub.2OH1178 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH1179 (CH.sub.2).sub.3O(CH.sub.2).sub.4OH__________________________________________________________________________1180 ##STR508## CH.sub.2CH.sub.2CH.sub.2OH violet1181 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH violet1182 H bluish__________________________________________________________________________ red1183 ##STR509## CH.sub.2CH.sub.2CH.sub.2OH violet1184 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH__________________________________________________________________________1185 ##STR510## CH.sub.2CH.sub.2CH.sub.2OH__________________________________________________________________________1186 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH1187 ##STR511## CH.sub.2CH.sub.2CH.sub.2OH red__________________________________________________________________________1188 ##STR512## H orange1189 CH.sub.2CH.sub.2OH1190 CH.sub.2CH.sub.2CH.sub.2OH1191 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH__________________________________________________________________________1192 ##STR513## CH.sub.2CH.sub.3 orange1193 CH.sub.2CH.sub.2CH.sub.2OH1194 ##STR514##1195 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH1196 H__________________________________________________________________________1197 ##STR515## CH.sub.2CH.sub.2OH1198 CH.sub.2CH.sub.2CH.sub.2OH1199 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH__________________________________________________________________________1200 ##STR516## CH.sub.2CH.sub.2OH bluishred1201 CH.sub.2CH.sub.2CH.sub.2OH1202 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH1203 ##STR517##__________________________________________________________________________1204 ##STR518## CH.sub.2CH.sub.2OH bluish red1205 CH.sub.2CH.sub.2CH.sub.2OH1206 CH.sub.2 CH.sub.2OCH.sub.2CH.sub.2OH__________________________________________________________________________1207 ##STR519## CH.sub.2CH.sub.2CH.sub.2OH yellowish__________________________________________________________________________ red1208 ##STR520## CH.sub.2CH.sub.2OH bluish red1209 CH.sub.2CH.sub.2CH.sub.2OH1210 H__________________________________________________________________________1211 ##STR521## CH.sub.2CH.sub.2OH violet1212 CH.sub.2CH.sub.2CH.sub.2OH__________________________________________________________________________1213 ##STR522## CH.sub.2CH.sub.2CH.sub.2OH reddish__________________________________________________________________________ blue TABLE 4__________________________________________________________________________Coupling component: ##STR523##Example Diazo component R.sup.2 Shade__________________________________________________________________________1214 ##STR524## CH.sub.2CH.sub.2OH yellowish red1215 CH.sub.2CH.sub.2CH.sub.2OH1216 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH__________________________________________________________________________1217 ##STR525## H yellowish red1218 CH.sub.2CH.sub.2OH1219 CH.sub.2CH.sub.2OCOCH.sub.31220 CH.sub.2CH.sub.2CH.sub.2OH1221 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH1222 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OCHO1223 (CH.sub.2).sub.6 OH__________________________________________________________________________1224 ##STR526## CH.sub.2CH.sub.2CH.sub.2OH red1225 CH.sub.2CH.sub.2OH__________________________________________________________________________1226 ##STR527## H1227 CH.sub.2CH.sub.2OH1228 CH.sub.2CH.sub.2CH.sub.2OH1229 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH__________________________________________________________________________1230 ##STR528## H red1231 CH.sub.2CH.sub.2OH1232 CH.sub.2CH.sub.2CH.sub.2OH1233 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH1234 (CH.sub.2).sub.3O(CH.sub.2).sub.4OH__________________________________________________________________________1235 ##STR529## CH.sub.2CH.sub.2CH.sub.2OH violet__________________________________________________________________________1236 ##STR530## CH.sub.2CH.sub.2CH.sub.2OH1237 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH__________________________________________________________________________1238 ##STR531## CH.sub.2CH.sub.2CH.sub.2OH violet1239 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH__________________________________________________________________________1240 ##STR532## CH.sub.2CH.sub.2CH.sub.2OH reddish blue1241 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH__________________________________________________________________________1242 ##STR533## CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH blue__________________________________________________________________________1243 ##STR534## H red1244 CH.sub.2CH.sub.2OH1245 CH.sub.2CH.sub.2CH.sub.2OH1246 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH__________________________________________________________________________1247 ##STR535## CH.sub.2CH.sub.2CH.sub.2OH bluish red1248 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH__________________________________________________________________________1249 ##STR536## CH.sub.2CH.sub.2CH.sub.2OH bluish red1250 CH.sub.2CH.sub.2O(CH.sub.2).sub.2 OH__________________________________________________________________________1251 ##STR537## CH.sub.2CH.sub.2CH.sub.2OH red1252 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH__________________________________________________________________________ table 5__________________________________________________________________________dye: ##STR538##No. Y Y.sup.1 Y.sup.2 E Shade__________________________________________________________________________1345 Cl NO.sub.2 H CH.sub.3 yellowish red1346 Cl Cl CN CH.sub.3 orange1347 CN Br H CH.sub.3 yellow1348 CH.sub.3 NO.sub.2 H CH.sub.3 orange1349 OCH.sub.3 NO.sub.2 H CH.sub.3 yellowish red1350 SO.sub.2 CH.sub.3 NO.sub.2 H CH.sub.3 bluish red1351 CF.sub.3 H H CH.sub.3 yellow1352 CF.sub.3 Cl H CH.sub.3 yellow1353 CN CN H CH.sub.3 orange1354 H NO.sub.2 H C.sub.2 H.sub.5 orange1355 H NO.sub.2 H C.sub.3 H.sub.7 (n) orange__________________________________________________________________________ TABLE 6__________________________________________________________________________Coupling component: ##STR539##No. Diazo component R.sup.2 B B.sup.1 Shade__________________________________________________________________________1269 ##STR540## CH.sub.2CH.sub.2OH CH.sub.3 H reddish violet1270 CH.sub.2CH.sub.2OH H CH.sub.2 reddish violet1271 CH.sub.2CH.sub.2OH H Cl reddish violet__________________________________________________________________________1272 ##STR541## CH.sub.2CH.sub.2OH CH.sub.3 H bluish red__________________________________________________________________________1273 ##STR542## CH.sub.2CH.sub.2OH CH.sub.3 H orange1274 CH.sub.2CH.sub.2OH H CH.sub.3 orange__________________________________________________________________________1275 ##STR543## CH.sub.2CH.sub.2OH H CH.sub.3 yellow1276 CH.sub.2CH.sub.2OH C(CH.sub.3).sub.3 H yellow1277 CH.sub.2CH.sub.2OH H OCH.sub.3 yellow1278 CH.sub.2CH.sub.2CH.sub.2OH H CH.sub.3 yellow__________________________________________________________________________1279 ##STR544## CH.sub.2CH.sub.2CH.sub.2OH H CH.sub.3 red1280 CH.sub.2CH.sub.2OH H CH.sub.3 red__________________________________________________________________________1281 ##STR545## CH.sub.2CH.sub.2OH H CH.sub.3 yellowish red__________________________________________________________________________1282 ##STR546## CH.sub.2CH.sub.2OH H CH.sub.3 orange__________________________________________________________________________ TABLE 7__________________________________________________________________________Coupling component: ##STR547##Example Diazo component R.sup.2 Shade__________________________________________________________________________1283 ##STR548## H yellowish red1284 CH.sub.2CH.sub.2OH red1285 CH.sub.2CH.sub.2CH.sub.2OH red1286 ##STR549## yellowish red1287 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH__________________________________________________________________________1288 ##STR550## H yellowish red1289 CH.sub.2CH.sub.2OH1290 CH.sub.2CH.sub.2CH.sub.2OH1291 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH__________________________________________________________________________1292 ##STR551## H orange1293 CH.sub.2CH.sub.2OH1294 CH.sub.2CH.sub.2CH.sub.2OH1295 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH__________________________________________________________________________1296 ##STR552## H1297 CH.sub.2CH.sub.2OH1298 CH.sub.2CH.sub.2CH.sub.2OH__________________________________________________________________________1299 ##STR553## H red1300 CH.sub.2CH.sub.2OH1301 CH.sub.2CH.sub.2CH.sub.2OH__________________________________________________________________________1302 ##STR554## H yellow1303 CH.sub.2CH.sub.2OH__________________________________________________________________________ table 8__________________________________________________________________________dye: ##STR555##No. Y Y.sub.1 Y.sub.2 X Shade__________________________________________________________________________1304 CN H H H yellow1305 CN NO.sub.2 H CN red1306 CN NO.sub.2 Cl CN red1307 CN Cl H H orange1308 H NO.sub.2 H CN orange1309 Cl NO.sub.2 H H red1310 Cl Cl CN CN orange1311 CN Br H CN yellow1312 CH.sub.3 NO.sub.2 H CN orange1313 OCH.sub.3 NO.sub.2 H CN yellowish red1314 SO.sub.2 CH.sub.3 NO.sub.2 H CN bluish red1315 CF H H CN yellow1316 CF.sub.3 Cl H CN yellow1317 CN CN H CN orange1318 CN NO.sub.2 Br CN red1319 Cl NO.sub.2 H CN yellowish red1320 Br NO.sub.2 H CN yellowish red1321 H NO.sub.2 H H red1322 H NO.sub.2 H CONH.sub.2 yellowish red__________________________________________________________________________ Particular value attaches for example to dyes of the formulae: __________________________________________________________________________No. Shade__________________________________________________________________________1323 ##STR556## bluish red1324 ##STR557## bluish red1325 ##STR558## reddish violet1326 ##STR559## red1327 ##STR560## red1328 ##STR561## red1329 ##STR562## red1330 ##STR563## yellowish red1331 ##STR564## orange1332 ##STR565## yellowish red1333 ##STR566## yellowish__________________________________________________________________________ red TABLE 9__________________________________________________________________________Dye ##STR567##No. Y Y.sup.1 Y.sup.2 E R.sup.2 Shade__________________________________________________________________________1354 SO.sub.2 CH.sub.3 NO.sub.2 H CH.sub.3 CH.sub.2CH.sub.2OH red1355 SO.sub.2 CH.sub.3 NO.sub.2 H C.sub.3 H.sub.7 (n) CH.sub.2CH.sub.2OH red1356 SO.sub.2 CH.sub.3 NO.sub.2 H C.sub.5 H.sub.11 (n) CH.sub.2CH.sub.2OH red1357 CN NO.sub.2 H CH.sub.3 CH.sub.2CH.sub.2OH red1358 CN Cl H CH.sub.3 CH.sub.2CH.sub.2OH yellow1359 CN H H CH.sub.3 CH.sub.2CH.sub.2OH yellow__________________________________________________________________________ TABLE 10__________________________________________________________________________Dye ##STR568##No. Y Y.sup.1 Y.sup.2 E Shade__________________________________________________________________________1340 CN H H CH.sub.3 yellow1341 CN NO.sub.2 H CH.sub.3 red1342 CN NO.sub.2 Cl CH.sub.3 red1343 CN Cl H CH.sub.3 yellow1344 H NO.sub.2 H CH.sub.3 orange__________________________________________________________________________

EXAMPLE 1356

9.8 parts of 2-amino-5,nitrobenzonitrile is added to 0.degree. to 4.degree. C in portions while stirring well to a mixture of 48 parts of concentrated sulfuric acid and 19.6 parts of 23% nitrosylsulfuric acid. The diazo solution is stirred for from four to five hours at 0.degree. to 4.degree. C and the diazonium salt mixture is then added in portions to a solution or suspension, cooled to 0.degree. C, of 23.5 parts of the coupling component of the formula: ##STR569## which contains a minor fraction of the coupling component of the formula: ##STR570## in a mixture of 150 parts by volume of glacial acetic acid, 20 parts by volume of concentrated hydrochloric acid, 1 part of sulfamic acid and 500 parts by volume of water. Sodium acetate and ice are added during coupling so that the pH of the mixture is always from 0 to 2, the temperature is about 0.degree. C and the mixture remains easily stirred. After coupling is over (it proceeds very rapidly at pH 1 to 2) the pricipitated dye mixture of the formula: ##STR571## (which contains a minor amount of the 2,6-dialkylaminopyridine isomer) is suction filtered and the residue washed with water and dried. A reddish brown powder is obtained which dissolves in dimethylformamide with a red color and dyes polyethylene terephthalate cloth red shades of excellent light fastness.

EXAMPLE 1357

8.8 parts of the diazo component of the formula: ##STR572## is stirred in 24 parts of concentrated sulfuric acid at 10.degree. to 15.degree. C. The whole is then cooled to 8.degree. to 10.degree. C and at this temperature 70 parts by volume of glacial acetic acid and 12 parts by volume of propionic acid are added while cooling. After further cooling to 0.degree. to 4.degree. C 13 parts of nitrosylsulfuric acid is dripped in and the whole is stirred for three hours at 0.degree. to 4.degree. C. The diazonium salt solution thus obtained is added to 13.1 parts of a solution or suspension, cooled to 0.degree. C, of the coupling component of the formula: ##STR573## (a minor portion of the coupling component consisting of the 2,6-dialkylaminopyridine isomer) in a mixture of 150 parts by volume of glacial acetic acid, 15 parts by volume of concentrated hydrochloric acid, 500 parts of water and 1 part of sulfamic acid.

Ice and sodium acetate are added during coupling so that the temperature does not rise above 0.degree. C and the pH remains at from 2 to about 0. Ice-water may also be added if the mixture becomes too difficult to stir.

Coupling is rapidly ended at pH 2. The precipitated dye mixture of the formulae: ##STR574## is filtered off, washed with water and dried. A brown powder is obtained which dissolves in dimethylformamide with an orange red color and dyes polyethylene terephthalate cloth orange shades of excellent light fastness.

EXAMPLE 1358

5.5 parts of p-nitroaniline is stirred with 40 parts by volume of water and 15 parts by volume of concentrated hydrochlirc acid. The whole is then diluted with ice and hydrochloric acid to a volume of 200 parts by volume, 13 parts by volume of 23% sodium nitrite solution is added and the whole is stirred for two hours. After the diazonium salt solution has been filtered any excess of nitrous acid present is destroyed as usual and the diazonium salt solution is added to a solution or dispersion, cooled to 5.degree. C, of 10 parts of the coupling component: ##STR575## in 250 parts of water and 20 parts of concentrated hydrochloric acid. The pH of the coupling mixture is raised to 2 to 3 by stewing in sodium acetate so that the coupling is rapidly ended. The precipitated dye of the formula: ##STR576## is suction filtered, washed with water and dried. About 15 parts of a yellowish red powder is obtained which dissolves in dimethylformamide with an orange color and dye polyethylene terephthalate cloth full orange shades having very good fastness to light and dry-heat pleating the setting by the carrier and HT methods.

The dyes set out in the following Tables can be prepared by the methods described in Examples 1356 to 1358:

TABLE 1__________________________________________________________________________ ##STR577##Example D-NH Z.sup.1 Z.sub.2 Shade__________________________________________________________________________1359 ##STR578## (CH.sub.2).sub.3O(CH.sub.2CH.sub.2O).sub.2CH.sub.2 (CH.sub.2).sub.3 O(CH.sub.2).sub.4 OH yellow1360 ##STR579## (CH.sub.2).sub.3 O(CH.sub.2).sub.6 H "1361 " (CH.sub.2).sub.3 O(CH.sub.2 CH.sub.2 O).sub.2 C.sub.2 ".sub.5__________________________________________________________________________1362 ##STR580## H (CH.sub.2).sub.3 O(CH.sub.2).sub.6 H yellowish__________________________________________________________________________ red1363 ##STR581## H (CH.sub.2).sub.3 O(CH.sub.2).sub.6 OH red1364 ##STR582## ##STR583## CH.sub.2CH.sub.2OH orange1365 " ##STR584## " orange1366 ##STR585## ##STR586## " yellow1367 ##STR587## " " red__________________________________________________________________________ TABLE 2__________________________________________________________________________ ##STR588##Ex. D-NH.sub.2 Z.sup.1 Z.sup.2 Shade__________________________________________________________________________1368 ##STR589## (CH.sub.2).sub.3OC.sub.2 H.sub.4OC.sub.2 H.sub.5 " yellow1369 " (CH.sub.2).sub.3OC.sub.2 H.sub.4OC.sub.6 H.sub.5 " "1370 " ##STR590## " "1371 " ##STR591## CH.sub.2CH.sub.2OH "1372 " (CH.sub.2).sub.3OCH.sub.2CH.sub.2C.sub.6 H.sub.5 " "1373 " (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5 " "1374 " H (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5 "1375 " H (CH.sub.2).sub.3O(C.sub.2 H.sub.4).sub.3 C.sub.6 H.sub.5 "1376 ##STR592## (CH.sub.2).sub.3OCH.sub.2CH.sub.2 OCH.sub.2 C.sub.6 H.sub.5 CH.sub.2CH.sub.2OH "1377 " H (CH.sub.2).sub.3O(C.sub.2 H.sub.4 O).sub.3 C.sub.6 "sub.51378 " ##STR593## CH.sub.2CH.sub.2OH "1379 " (CH.sub.2).sub.2OC.sub.6 H.sub.5 " "1380 " (CH.sub.2).sub.3OC.sub.6 H.sub.5 " "1381 " ##STR594## " "1382 " (CH.sub.2).sub.3O(CH.sub.2).sub.6OH " "1383 " ##STR595## " "1384 ##STR596## ##STR597## " orange1385 " (CH.sub.2).sub.3(OC.sub.2 H.sub.4).sub.2OCH.sub.3 " "1386 " (CH.sub.2).sub.3(OC.sub.2 H.sub.4).sub.3OC.sub.2 ".sub.5 "1387 " (CH.sub.2).sub.3(OC.sub.2 H.sub.4).sub.4OC.sub.2 ".sub.5 "1388 " (CH.sub.2).sub.3(OCHCH.sub.2).sub.2OCH.sub.3 " "1389 " H (CH.sub.2).sub.3(OC.sub.2 H.sub.4).sub.3 OCH.sub.3 "1390 " H ##STR598## "1391 " H CH.sub.2CHOC.sub.6 H.sub.5 "1392 " H (CH.sub.2).sub.3(O CH.sub.2CH.sub .2).sub.2 - OC.sub.6 H.sub.5 "1393 " H ##STR599##1394 " (CH.sub.2).sub.3(OC.sub.2 H.sub.4).sub.2OC.sub.6 CH.sub.2CH.sub.2OH "1395 " ##STR600## " "1396 " (CH.sub.2).sub.3OC.sub.2 H.sub.4OCH.sub.2C.sub.6 ".sub.5 "1397 ##STR601## (CH.sub.2).sub.3OC.sub.2 H.sub.4OCH.sub.2C.sub.6 ".sub.5 "1398 " (CH.sub.2).sub.3OC.sub.2 H.sub.4OCH(CH.sub.3).sub.2 " "1399 " (CH.sub.2).sub.3OC.sub.2 H.sub.4C.sub.6 H.sub.5 " "1400 ##STR602## " " yellowish red1401 " " (CH.sub.2).sub.3OH "1402 " (CH.sub.2).sub.3(OC.sub.2 H.sub.4).sub.2OC.sub.6 ".sub.5 "1403 " ##STR603## CH.sub.2CH.sub.2OH "1404 ##STR604## H (CH.sub.2).sub.3OCH.sub.2C.sub. 6 H.sub.5 "1405 " H (CH.sub.2).sub.3OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 "1406 " (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5 CH.sub.2CH.sub.2OH "1407 ##STR605## " " "1408 " (CH.sub.2).sub.3OCHCH.sub.2OC.sub.6 H.sub.5 " "1409 ##STR606## H (CH.sub.2).sub.3(OCH.sub.2 CH.sub.2).sub.3 OC.sub.6 yellow51410 " ##STR607## CH.sub.2CH.sub.2OH "1411 " (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5 " "1412 ##STR608## (CH.sub.2).sub.3(OC.sub.2 H.sub.4).sub.3OC.sub.6 CH.sub.2CH.sub.2OH "1413 " (CH.sub.2).sub.3(OC.sub.2 H.sub.4).sub.4OC.sub.2 ".sub.5 "1414 " " (CH.sub.2).sub.3OH "1415 ##STR609## " " "1416 " H (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5 "1417 ##STR610## " "1418 " (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5 CH.sub.2CH.sub.2OH "1419 ##STR611## " " orange1420 ##STR612## ##STR613## CH.sub.2CH.sub.2OH "1421 ##STR614## " " red1422 " (CH.sub.2).sub.3O(CH.sub.2).sub.6OH H yellowish red1423 " H (CH.sub.2).sub.3O(CH.sub.2).sub.6 OH "1424 " CH.sub.2COC.sub.6 H.sub.5 CH.sub.2CH.sub.2OH red1425 " CH.sub.2CH.sub.2OC.sub.6 H.sub.5 " "1426 ##STR615## H (CH.sub.2).sub.3O(CH.sub.2).sub.6 H orange1427 " H (CH.sub.2).sub.3O(C.sub.2 H.sub.4 O).sub.2C.sub.6 H.sub.5 "1428 " H (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5 "1429 " (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5 H "1430 " (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5 " "1431 " (CH.sub.2).sub.3OC.sub.2 H.sub.4OC.sub.2 H.sub.5 " "1432 " ##STR616## " "1433 " (CH.sub.2).sub.3(OCHCH.sub.2).sub.2OCH.sub.3 " "1434 ##STR617## (CH.sub.2).sub.3O (CH.sub.2 CH.sub.2 O).sub.2 CH.sub.3 " yellowish red1435 " (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5 " "1436 ##STR618## " " red1437 " H (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5 "1438 " (CH.sub.2).sub.3OC.sub.2 H.sub.4 OC.sub.4 H.sub.9 CH.sub.2CH.sub.2OH "1439 " (CH.sub.2).sub.3OC.sub.2 H.sub.4OCH(CH.sub.3).sub.2 " "1440 " (CH.sub.2).sub.3O(CH.sub.2).sub.2C.sub.6 H.sub.5 CH.sub.2CH.sub.2OH "1441 " (CH.sub.2).sub.3O(C.sub.2 H.sub.4 O).sub.2C.sub.6 H.sub.5 " "1442 ##STR619## " " "1443 " (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5 " "1444 " " (CH.sub.2).sub.3OH "1445 " (CH.sub.2).sub.3O(C.sub.2 H.sub.4 O).sub.2 C.sub.6 H.sub.5 CH.sub.2CH.sub.2OH "1446 " H (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5 "1447 ##STR620## (CH.sub.2).sub.3O(CH.sub.2).sub.2OH H orange1448 " (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5 " reddish blue1449 " " CH.sub.2CH.sub.2OH "1450 ##STR621## " " violet__________________________________________________________________________ TABLE 3__________________________________________________________________________ ##STR622##Ex. DNH.sub.2 Z.sup.1 Z.sup.2 Shade__________________________________________________________________________1451 ##STR623## (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5 CH.sub.2CH.sub.2OH reddish1452 ##STR624## (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5 CH.sub.2CH.sub.2OH bluish red1453 ##STR625## (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5 CH.sub.2CH.sub.2OH red__________________________________________________________________________ TABLE 4______________________________________Coupling component: ##STR626##______________________________________ in coupling with these coupling components mixtures are formed because the coupling may take place in the 3-position and also in the 5-position of the pyridine ring: __________________________________________________________________________ DiazoNo. component Z.sup.1 Z.sup.2 Shade__________________________________________________________________________1454 ##STR627## (CH.sub.2).sub.3OCH.sub.2 C.sub.6 H.sub.5 CH.sub.2CH.sub.2OH greenish blue1455 " " (CH.sub.2).sub.3OH "1456 " (CH.sub.2).sub.3OC.sub.2 H.sub.4OC.sub.2 H.sub.5 CH.sub.2CH.sub.2OH "1457 ##STR628## (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5 " reddish violet1458 ##STR629## " " "1459 " ##STR630## " "1460 ##STR631## " " "1461 " (CH.sub.2).sub.4OCH.sub.2C.sub.6 H.sub.5 " "1462 ##STR632## CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5 (CH.sub.2).sub.3OH bluish red__________________________________________________________________________

The dyes set out in Table 5 are also particularly valuable. They are distinguished by high yield and high fastness to dry-heat pleating and setting.

TABLE 5______________________________________Coupling component: ##STR633## DiazoNo. component Shade______________________________________1463 ##STR634## 2 red1464 " 3 "1465 ##STR635## 2 bluish red1466 " 3 "1467 ##STR636## 2 yellowish red1468 " 3 "1469 ##STR637## 2 bluish red1470 " 3 "1471 ##STR638## 2 "1472 " 3 "1473 ##STR639## 2 "1484 " 3 "1475 ##STR640## 2 yellow1476 " 3 "1477 ##STR641## 2 reddish violet1478 " 3 "1479 ##STR642## 2 orange1480 " 3 "1481 ##STR643## 2 red1482 " 3 "1483 ##STR644## 2 orange1484 " 3 "______________________________________ TABLE 6__________________________________________________________________________Coupling component: ##STR645##No. D-NH.sub.2 n Z.sup.1 Shade__________________________________________________________________________1485 ##STR646## 2 (CH.sub.2).sub.3O(CH.sub.2).sub.2 OH yellow1486 " 3 " "1487 " 6 " "1488 ##STR647## 2 " orange1489 " 6 " "1490 ##STR648## 2 " yellowish red1491 " 3 " "1492 ##STR649## 2 " bluish red1493 " 3 " "1494 ##STR650## 2 (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5 yellow1495 ##STR651## 2 " "__________________________________________________________________________ The dye of the formula:1496 ##STR652## red__________________________________________________________________________ TABLE 7__________________________________________________________________________Coupling component: ##STR653##No. Diazo component Z.sup.2 Shade__________________________________________________________________________1497 ##STR654## C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH yellow1498 " C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3 "1499 ##STR655## ##STR656## "1500 " C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH "1501 ##STR657## " "1502 " ##STR658## "1503 ##STR659## C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH "1504 ##STR660## " orange1505 ##STR661## " "1506 ##STR662## " orange1507 " (CH.sub.2).sub.3 O(CH.sub.2).sub.6 OH "1508 ##STR663## C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH yellowish red1509 " (CH.sub.2).sub.3 (OC.sub.2 H.sub.4).sub.2 OCH.sub.3 "1510 ##STR664## C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH "1511 ##STR665## " "1512 ##STR666## " yellow1513 ##STR667## " orange1514 ##STR668## " yellow1515 ##STR669## " "1516 ##STR670## " "1517 ##STR671## " orange1518 ##STR672## " yellow1519 ##STR673## " "1520 ##STR674## " "1521 ##STR675## " yellowish red1522 ##STR676## " "1523 ##STR677## " red1524 ##STR678## " "1525 ##STR679## " "1526 ##STR680## " "1527 ##STR681## " "1528 ##STR682## " yellowish red1529 ##STR683## " "1530 ##STR684## " bluish red1531 ##STR685## " red1532 ##STR686## " yellow1533 ##STR687## " "1534 ##STR688## (CH.sub.2).sub.3 O(CH.sub.2).sub.4 OH red1535 ##STR689## " reddish blue1536 " C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH "1537 ##STR690## " "1538 ##STR691## " "1539 ##STR692## " yellowish blue1540 ##STR693## " yellow1541 ##STR694## " "1542 ##STR695## " bluish red1543 ##STR696## " "1544 ##STR697## " "1545 " (CH.sub.2).sub.3 O(CH.sub.2).sub.4 OH "1546 ##STR698## C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH violet1547 ##STR699## C.sub.2 H.sub. 4 OC.sub.2 H.sub.4 OH violet1548 "X = CN " bluish violet1549 ##STR700## " orange1550 ##STR701## " "1551 ##STR702## " violet1552 ##STR703## " bluish red1553 ##STR704## " "1554 ##STR705## ##STR706## orange1555 " (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OH "1556 " ##STR707## "1557 " ##STR708## "1558 " ##STR709## "1559 " (CH.sub.2).sub.3 OC.sub.6 H.sub.5 "1560 " (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5 "1561 " (CH.sub.2).sub.3 OC.sub.2 H.sub.4 C.sub.6 H.sub.5 "1562 " (CH.sub.2).sub.3 OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 "1563 " CH.sub.2 CHOHC.sub.6 H.sub.5 "__________________________________________________________________________

when 2-cyano-4-chloroaniline is used in the case of Examples 1554 to 1563, compounds which give yellow shades are obtained.

TABLE 8______________________________________Coupling component: ##STR710##No. Diazo component Z.sup.1 Shade______________________________________1564 ##STR711## (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OH yellow1565 ##STR712## ##STR713## "1566 ##STR714## C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH "1567 ##STR715## " orange1568 ##STR716## " "1569 ##STR717## " yellow1570 ##STR718## " yellow- ish red1571 ##STR719## " "1572 ##STR720## " red1573 ##STR721## " "1574 ##STR722## (CH.sub.2).sub.3 O(CH.sub.2).sub.4 OH red1575 ##STR723## C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH "1576 ##STR724## " violet1577 ##STR725## " reddish blue1578 ##STR726## " blue1579 ##STR727## " red1580 ##STR728## " bluish red1581 ##STR729## " bluish red1582 ##STR730## " red______________________________________ TABLE 9______________________________________Coupling component: ##STR731##No. Diazo component X Z.sup.2 Shade______________________________________1583 ##STR732## H C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH yellow- ish red1584 ##STR733## H " "1585 ##STR734## H " orange1586 ##STR735## CONH.sub.2 " red1587 ##STR736## " " reddish violet______________________________________

EXAMPLE 1588

A mixture of 187 parts of 2,6-dichloro-3-cyano-4-ethylpyridine, 500 parts of methanol and 135 parts of 2-phenylpropylamine-(1) is stirred for an hour at from about 25.degree. to a maximum of 55.degree. C, then 105 parts of triethylamine is added within fifteen minutes and the whole is stirred for another six hours at about 45.degree. to 55.degree. C. About 250 parts by volume of methanol is distilled off at subatmospheric pressure with the excess triethylamine, the whole is allowed to cool somewhat and the residue is added while stirring to a mixture of about 1500 parts of water, 500 parts of ice and 50 parts of concentrated hydrochloric acid. Stirring is continued for one hour and the precipitate is suction filtered and dried. About 265 parts of a colorless powder is obtained which melts at 85.degree. to 90.degree. C.

27.5 parts of this powder is stirred with about 60 parts of .beta.-hydroxyethylamine for from four to five hours at 130.degree. to 155.degree. C. The whole is allowed to cool and 200 parts by volume of glacial acetic acid and 30 parts by volume of concentrated hydrochloric acid are added to the mixture. A solution of the coupling component of the probable formula: ##STR737## is obtained which contains a minor proportion of the coupling component of the probable formula: ##STR738##

The coupling component mixture has about 50 parts of ice added to it and is cooled to about 0.degree. C. Then there are added in portions at the same time about 100 parts of ice and a solution of diazotized 2-amino-4-nitro-benzonitrile which has been prepared as follows: 16.3 parts of 2-amino-5-nitrobenzonitrile is added while stirring at 0.degree. to 4.degree. C into a mixture of 50 parts of concentrated sulfuric acid and 13 parts of 23% nitrosylsulfuric acid so that the temperature does not at any time rise above 4.degree. C. The whole is stirred for four hours at 0.degree. to 5.degree. C and then coupled as described above. In order to achieve rapid completion of the coupling, which should proceed at about 0.degree. C, the pH of the mixture is adjusted to be from 1.5 to 2.5 by adding sodium acetate. If the mixture should become difficult to stir during the coupling, ice-water may be added.

The mixture is stirred for another hour, heated with steam to 60.degree. to 80.degree. C, suction filtered, washed with water and dried. About 47 parts of a reddish brown powder of the probable formula: ##STR739## is obtained which contains a smaller dye fraction of the 2,6-alkyl-aminopyridine isomers. It dissolves in dimethylformamide with a red color and dyes polyethylene terephthalate cloth full red shades having excellent fastness properties.

TABLE 1______________________________________ ##STR740##______________________________________No. R X Y Shade______________________________________1589 C.sub.2 H.sub.5 CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 bluish red______________________________________ TABLE 2__________________________________________________________________________ ##STR741##__________________________________________________________________________No. R X Y Shade__________________________________________________________________________1590 C.sub.3 H.sub.7 CH.sub.2CH.sub.2OH (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5 red1591 C.sub.3 H.sub.7 H C.sub.6 H.sub.5 bluish red__________________________________________________________________________ TABLE 3__________________________________________________________________________ ##STR742##__________________________________________________________________________No. R X Y Shade__________________________________________________________________________1592 C.sub.3 H.sub.7 CH.sub.2CH.sub.2OH (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5 red1593 C.sub.3 H.sub.7 H C.sub.6 H.sub.5 bluish red__________________________________________________________________________ TABLE 4__________________________________________________________________________ ##STR743##__________________________________________________________________________No. R X Y Shade__________________________________________________________________________1594 C.sub.3 H.sub.7 CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 bluish red1595 C.sub.3 H.sub.7 CH.sub.2CH.sub.2OH ##STR744## red__________________________________________________________________________ TABLE 5__________________________________________________________________________ ##STR745##__________________________________________________________________________No. R X Y Shade__________________________________________________________________________1596 C.sub.2 H.sub.5 CH.sub.2CH.sub.2OCH.sub.2 CH.sub.2OH C.sub.6 H.sub.5 yellowish red1597 C.sub.2 H.sub.5 CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 yellowish red__________________________________________________________________________ TABLE 6__________________________________________________________________________ ##STR746##__________________________________________________________________________No. R X Y Shade__________________________________________________________________________ 1598 C.sub.2 H.sub.5 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH C.sub.6 H.sub.5 yellowish red1599 C.sub.2 H.sub.5 CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 yellowish red__________________________________________________________________________ TABLE 7__________________________________________________________________________ ##STR747##__________________________________________________________________________No. R X Y Shade__________________________________________________________________________1600 C.sub.3 H.sub.7 (n) CH.sub.2CH.sub.2OH ##STR748## reddish orange1601 C.sub.3 H.sub.7 (n) CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 yellowish red1602 C.sub.2 H.sub.5 CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 yellowish red1603 C.sub.2 H.sub.5 CH.sub.2CH.sub.2OCH.sub.2OH.sub.2OH C.sub.6 H.sub.5 yellowish red__________________________________________________________________________ TABLE 8__________________________________________________________________________ ##STR749##No. R X Y Shade__________________________________________________________________________1604 C.sub.2 H.sub.5 CH.sub.2CH.sub.2OH (CH.sub.2).sub.3O(CH.sub.2).sub.6OH red1605 C.sub.3 H.sub.7 (n) CH.sub.2CH.sub.2OH ##STR750## "1606 C.sub.2 H.sub.5 CH.sub.2CH.sub.2OH ##STR751## "1607 C.sub.3 H.sub.7 (n) CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 "1608 C.sub.2 H.sub.5 CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 "1609 C.sub.3 H.sub.7 (n) CH.sub.2CH.sub.2OH ##STR752## "1610 C.sub. 3 H.sub.7 (n) CH.sub.2CH.sub.2OH ##STR753## "__________________________________________________________________________ table 9__________________________________________________________________________ ##STR754##No. R X Y Shade__________________________________________________________________________1611 C.sub.2 H.sub.5 CH.sub.2CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 yellow to orange1612 C.sub.2 H.sub.5 CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 "1613 C.sub.3 H.sub.7 (n) H ##STR755## yellow1614 C.sub.3 H.sub.7 (n) ##STR756## H "1615 C.sub.3 H.sub.7 (n) ##STR757## CH.sub.2CH.sub.2OH "__________________________________________________________________________ table 10______________________________________ ##STR758##no. R X Y Shade______________________________________1616 C.sub.3 H.sub.7 (n) CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 yellow1617 C.sub.3 H.sub.7 (n) CH.sub.2CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 "______________________________________ table 11__________________________________________________________________________ ##STR759##no. R X Y Shade__________________________________________________________________________1618 C.sub.2 H.sub.5 H (CH.sub.2).sub.3O(CH.sub.2).sub.6OH yellowish red1619 C.sub.3 H.sub.7 (n) CH.sub.2CH.sub.2OH ##STR760## red1620 C.sub.2 H.sub.5 CH.sub.2CH.sub.2OH ##STR761## "1621 C.sub.3 H.sub.7 (n) CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 "1622 C.sub.2 H.sub.5 CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 "1623 C.sub.3 H.sub.7 (n) CH.sub.2CH.sub.2 OH ##STR762## "1624 C.sub.3 H.sub.7 (n) CH.sub.2CH.sub.2OH ##STR763## "__________________________________________________________________________ tale 12______________________________________ ##STR764##no. R X Y Shade______________________________________1625 C.sub.2 H.sub.5 CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 red______________________________________ TABLE 13______________________________________ ##STR765##No. R X Y Shade______________________________________1626 C.sub.2 H.sub.5 CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 red______________________________________ TABLE 14__________________________________________________________________________ ##STR766##No. R X Y Shade__________________________________________________________________________1627 C.sub.2 H.sub.5 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH C.sub.6 H.sub.5 blue1628 C.sub.2 H.sub.5 CH.sub.2CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 blue1629 C.sub.2 H.sub.5 CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 blue1630 C.sub.3 H.sub.7 (n) (CH.sub.2).sub.3O(CH.sub.2).sub.6OH H violet__________________________________________________________________________ TABLE 15__________________________________________________________________________ ##STR767##No. R X Y Shade__________________________________________________________________________1631 C.sub.3 H.sub.7 (n) CH.sub.2CH.sub.2OH (CH.sub.2).sub.3O(CH.sub.2).sub.2O(CH.sub.2).sub. 2OCH.sub.3 reddish violet1632 C.sub.3 H.sub.7 (n) H C.sub.6 H.sub.5 reddish violet1633 C.sub.3 H.sub.7 (n) CH.sub.2CH.sub.2OH ##STR768## reddish violet1634 C.sub.3 H.sub.7 (n) (CH.sub.2).sub.2O(CH.sub.2).sub.2OH ##STR769## reddish violet__________________________________________________________________________ TABLE 16__________________________________________________________________________ ##STR770##No. A R X Y Shade__________________________________________________________________________1635 ##STR771## C.sub.2 H.sub.5 CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 orange CH.sub.2CH.sub.21636 ##STR772## C.sub.3 H.sub.7 (n) CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 orange CH.sub.2CH.sub.21637 ##STR773## C.sub.3 H.sub.7 (n) CH.sub.2CH.sub.2CH.sub.2 OH C.sub.6 H.sub.5 orange1638 CH.sub.3 OCOCH.sub.2 CH.sub.2 C.sub.3 H.sub.7 (n) CH.sub.2CH.sub.2OH ##STR774## orange__________________________________________________________________________ TABLE 17__________________________________________________________________________ ##STR775##No. A X Y Shade__________________________________________________________________________1639 C.sub.3 H.sub.7 (n) CH.sub.2CH.sub.2OH ##STR776## reddish orange1640 C.sub.3 H.sub.7 (n) CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 yellowish red1641 C.sub.2 H.sub.5 CH.sub.2CH.sub.2 OH C.sub.6 H.sub.5 yellowish red1642 C.sub.2 H.sub.5 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH C.sub.6 H.sub.5 yellowish red__________________________________________________________________________ TABLE 18__________________________________________________________________________ ##STR777##No. R X Y Shade__________________________________________________________________________1643 C.sub.3 H.sub.7 (n) CH.sub.2CH.sub.2OH ##STR778## orange1644 C.sub.3 H.sub.7 (n) CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 yellowish red1645 C.sub.2 H.sub.5 CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 yellowish red1646 C.sub.2 H.sub.5 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH C.sub.6 H.sub.5 yellowish red__________________________________________________________________________ TABLE 19__________________________________________________________________________ ##STR779##No. R X Y Shade__________________________________________________________________________1647 C.sub.3 H.sub.7 (n) CH.sub.2CH.sub.2OH ##STR780## orange1648 C.sub.3 H.sub.7 (n) CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 yellowish red1649 C.sub.2 H.sub.5 CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 yellowish red1650 C.sub.2 H.sub.5 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH C.sub.6 H.sub.5 yellowish red__________________________________________________________________________ TABLE 20__________________________________________________________________________ ##STR781##No. R X Y Shade__________________________________________________________________________1651 C.sub.3 H.sub.6 (n) CH.sub.2CH.sub.2OH ##STR782## yellow1652 C.sub.3 H.sub.7 (n) CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 orange1653 C.sub.2 H.sub.5 CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 orange1654 C.sub.2 H.sub.5 CH.sub.2CH.sub.2OCH.sub.2CH.sub.2OH C.sub.6 H.sub.5 orange__________________________________________________________________________ TABLE 21__________________________________________________________________________ ##STR783##No. R X Y Shade__________________________________________________________________________1655 C.sub.2 H.sub.5 CH.sub.2CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 yellow to orange1656 C.sub.2 H.sub.5 CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 yellow to orange1657 C.sub.3 H.sub.7 (n) H ##STR784## yellow1658 C.sub.3 H.sub.7 (n) ##STR785## H yellow1659 C.sub.3 H.sub.7 (n) ##STR786## CH.sub.2CH.sub.2OH yellow__________________________________________________________________________ TABLE 22__________________________________________________________________________ ##STR787##No. R X Y Shade__________________________________________________________________________1660 C.sub.2 H.sub.5 CH.sub.2CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 yellow to orange1661 C.sub.2 H.sub.5 CH.sub.2CH.sub.2OH C.sub.6 H.sub.5 yellow to orange1662 C.sub.3 H.sub.7 (n) H ##STR788## yellow1663 C.sub.3 H.sub.7 (n) ##STR789## H yellow1664 C.sub.3 H.sub.7 (n) ##STR790## CH.sub.2CH.sub.2OH yellow__________________________________________________________________________ TABLE 23__________________________________________________________________________ ##STR791##No. R X Y Shade__________________________________________________________________________1665 C.sub.3 H.sub.7 CH.sub.2CH.sub.2OH (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5 bluish red1666 C.sub.3 H.sub.7 (n) H C.sub.6 H.sub.5 bluish red__________________________________________________________________________ TABLE 24__________________________________________________________________________ ##STR792##No. R X Y Shade__________________________________________________________________________1667 C.sub.3 H.sub.7 (n) CH.sub.2CH.sub.2OH (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5 bluish red1668 C.sub.3 H.sub.7 H C.sub.6 H.sub.5 bluish red__________________________________________________________________________ TABLE 25__________________________________________________________________________ ##STR793##No. R X Y Shade__________________________________________________________________________1669 C.sub.3 H.sub.7 (n) CH.sub.2CH.sub.2OH (CH.sub.2).sub.3OCH.sub.2C.sub.6 H.sub.5 bluish red1670 C.sub.3 H.sub.7 (n) H C.sub.6 H.sub.5 bluish red__________________________________________________________________________ TABLE 26__________________________________________________________________________ ##STR794##No. R.sup.1 R.sup.2 R.sup.3 R.sup.4 Shade__________________________________________________________________________1671 (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OH C.sub.2 H.sub.5 CH.sub.3 pink1672 H (CH.sub.2).sub.3 O(CH.sub.2).sub.6 OH C.sub.3 H.sub.7 CH.sub.3 pink1673 H (CH.sub.2).sub.3 O(CH.sub.2).sub.6 OH CH.sub.3 CH.sub.3 pink1674 H ##STR795## CH.sub.3 CH.sub.3 pink1675 H (CH.sub.2).sub.3 O(CH.sub.2).sub.2 OH CH.sub.3 CH.sub.3 pink1676 H (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 pink1677 H ##STR796## CH.sub.3 CH.sub.3 pink1678 (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5 CH.sub.2 CH.sub.2 OH C.sub.2 H.sub.5 CH.sub.3 bluish red1679 (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5 (CH.sub.2).sub.3 OH C.sub.2 H.sub.5 CH.sub.3 bluish red1680 (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5 (CH.sub.2).sub.3 OH CH.sub.3 CH.sub.3 bluish red1681 (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5 CH.sub.2 CH.sub.2 OH CH.sub.3 CH.sub.3 bluish red1682 (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5 CH.sub.2 CH.sub.2 OH CH.sub.3 C.sub.2 H.sub.5 bluish red1683 (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5 (CH.sub.2).sub.3 OH CH.sub.3 C.sub.2 H.sub.5 bluish red1684 ##STR797## (CH.sub.2).sub.3 OH CH.sub.3 C.sub.2 H.sub.5 bluish red1685 ##STR798## CH.sub.2 CH.sub.2 OH CH.sub.3 C.sub.2 H.sub.5 bluish red1686 ##STR799## CH.sub.2 CH.sub.2 OH CH.sub.3 CH.sub.3 bluish red1687 ##STR800## (CH.sub.2).sub.3 OH C.sub.2 H.sub.5 CH.sub.3 bluish red__________________________________________________________________________

Claims

1. A dye of the formula ##STR801## wherein: D is phenyl substituted by chlorine, bromine, trifluoromethyl, methyl, methoxy, nitro, cyano, methylsulfonyl, phenylsulfonyl, carbalkoxy of a total of 2 to 5 carbon atoms, carbo-.beta.-alkoxy-ethoxy, said alkoxy having 1 to 4 carbon atoms, or N,N-dialkyl- or N-monoalkyl-substituted sulfamoyl, each alkyl having 1 to 4 carbon atoms; phenylazophenyl; phenylazophenyl substituted by methyl, chlorine, bromine or nitro; benzthiazolyl; benzthiazolyl substituted by nitro, cyano, methylsulfonyl or ethylsulfonyl; benzisothiazolyl substituted by chlorine, bromine, cyano or nitro; thiazolyl substituted by cyano or nitro; thienyl substituted by methyl, cyano, nitro or carbalkoxy of a total of 2 to 5 carbon atoms; or thiadiazolyl substituted by phenyl, methyl, chlorine, bromine, methylmercapto, ethylmercapto or alkoxycarbonylethylmercapto, said alkoxy having 1 to 4 carbon atoms;

R is alkyl of 1 to 3 carbon atoms;

X is carbamoyl or cyano;

R.sup.1 and

R.sup.2 may be the same or different with the proviso that one of R.sup.1 and R.sup.2 is C.sub.6 H.sub.5 ; ##STR802## (CH.sub.2).sub.3 OCH.sub.2 CH.sub.2 OH; (CH.sub.2).sub.3 O(CH.sub.2).sub.6 OH; ##STR803## (CH.sub.2).sub.3 OC.sub.2 H.sub.4 OR.sup.7, (CH.sub.2).sub.3 (OC.sub.2 H.sub.4).sub.q OR.sup.8, (CH.sub.2).sub.3 OR.sup.9 ; ##STR804## C.sub.2 H.sub.4 OC.sub.6 H.sub.5, C.sub.2 H.sub.4 OC.sub.6 H.sub.4 CH.sub.3 ; ##STR805## and the other of R.sup.1 and R.sup.2 is hydrogen; alkyl of 1 to 8 carbon atoms; alkyl of 2 to 8 carbon atoms substituted by hydroxy, alkoxy of 1 to 8 carbon atoms, formyloxy, acetoxy, propionyloxy, carboxy, cyclohexoxy, benzyloxy, phenylethoxy, phenoxy or pyrrolidonyl; cyclohexyl; methylcyclohexyl; benzyl; phenylethyl; .beta.-phenyl-.beta.-hydroxyethyl; phenyl; tolyl; CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OH; (CH.sub.2).sub.3 OC.sub.6 H.sub.5 --CH.sub.3 ; (CH.sub.2).sub.3 O(CH.sub.2).sub.4 OH; ##STR806## (CH.sub.2).sub.3 OC.sub.2 H.sub.4 OCH.sub.3 ; (CH.sub.2).sub.3 OC.sub.2 H.sub.4 OC.sub.6 H.sub.5 ; ##STR807## (CH.sub.2).sub.3 OCH.sub.2 CH.sub.2 OH; (CH.sub.2).sub.3 O(CH.sub.2).sub.6 OH; ##STR808## (CH.sub.2).sub.3 OC.sub.2 H.sub.4 OR.sup.7 ; (CH.sub.2).sub.3 (oc.sub.2 H.sub.4).sub.q OR.sup.8 ; ##STR809## C.sub.2 H.sub.4 OC.sub.6 H.sub.4 CH.sub.3 ; ##STR810## R.sup.3 is alkyl of one to three carbon atoms, hydroxymethyl or hydroxyethyl;

R.sup.4 is hydrogen, alkyl of one to three carbon atoms, hydroxymethyl or hydroxyethyl;

R.sup.5 is hydrogen or hydroxyl;

R.sup.6 is hydrogen, alkyl of 1 to 4 carbon atoms, methoxy, ethoxy or chloro; one of R.sup.3 to R.sup.5 providing a hydroxy group;

R.sup.7 is ethyl, propyl, butyl, cyclohexyl, benzyl, phenylethyl or methylphenyl;

R.sup.8 is hydrogen, alkyl of one to four carbon atoms, cyclohexyl, phenyl, methylphenyl, benzyl or phenylethyl;

R.sup.9 is cyclohexyl, phenyl, methylphenyl, benzyl or phenylethyl;

m is 1 or 2;

n is zero, 1 or 2;

q is 2, 3 or 4; and

p is 1, 2, 3 or 4.

2. A dye as claimed in claim 1 of the formula ##STR811## wherein: Y is nitro, cyano, chloro, bromo, carbomethoxy, carboethoxy, .beta.-methoxycarboethoxy, methylsulfonyl, ethylsulfonyl, methyl, methoxy or phenylazo;

Y.sup.1 is hydrogen, nitro, chloro, bromo, cyano, methyl, methoxy, carbomethoxy, carboethoxy, methylsulfonyl or ethylsulfonyl; and

Y.sup.2 is hydrogen, chloro, bromo, cyano, methyl, methoxy, carbomethoxy or carboethoxy; and

R.sup.1 and R.sup.2 have the same meanings as given in claim 1.

3. A dye as claimed in claim 1 wherein X is cyano.

4. A dye as claimed in claim 1 wherein:

X is cyano;

said one of R.sup.1 and R.sup.2 is C.sub.6 H.sub.5 ; ##STR812## (CH.sub.2).sub.3 OC.sub.2 H.sub.4 OH, (CH.sub.2).sub.3 O(CH.sub.2).sub.6 OH, ##STR813## (CH.sub.2).sub.3 OC.sub.2 H.sub.4 OCH.sub.2 C.sub.6 H.sub.5 ; (CH.sub.2).sub.3 (OC.sub.2 H.sub.4).sub.2 OR.sup.8 ; ##STR814## (CH.sub.2).sub.3 OC.sub.6 H.sub.5 ; (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5 or (CH.sub.2).sub.3 OC.sub.2 H.sub.4 C.sub.6 H.sub.5 ; and

said other of R.sup.1 and R.sup.2 is hydrogen; or alkyl of 2 to 8 carbon atoms substituted by hydroxy, alkoxy of 1 to 4 carbon atoms, formyloxy, acetoxy or propionyloxy.

5. The dye of the formula ##STR815##

6. The dye of the formula ##STR816##

7. The dye of the formula ##STR817##

8. The dye of the formula ##STR818##