Azo dyes having a benzoisothiazolyl diazo component

Abstract

P-aminoazo dyes of the formula: ##STR1## in which D is a benzoisothiazolyl group;B.sup.1 is hydrogen, methyl, ethyl, methoxy, ethoxy;B.sup.2 is hydrogen, methyl, ethyl, methoxy, ethoxy, chloro, bromo, C.sub.1 to C.sub.4 alkanoylamino or C.sub.1 to C.sub.4 alkoxycarbonylamino;R.sup.1 is the radical ##STR2## C.sub.1 to C.sub.4 alkyl optionally bearing hydroxy, C.sub.1 to C.sub.4 alkoxy, C.sub.1 to C.sub.4 alkanoyloxy, C.sub.1 to C.sub.4 alkoxycarbonyl, C.sub.1 to C.sub.4 alkanoylamino or chloro as a substituent, phenylethyl, phenoxyethyl or cyclohexyl and the group -A.sup.1 --CO--A.sup.2 represents acyl, acyloxy or acylamino derived from a carbonic acid derivative in which A.sup.1 is a single bond, --O--, --NH-- or ##STR3##

Description

The invention relates to dyes of the formula (I): ##STR4## in which D is a radical of the formula: ##STR5## X is nitro, chloro or bromo; Y is hydrogen, chloro or bromo;

Z is hydrogen, chloro, bromo or cyano; B.sup.1 is hydrogen, methyl, ethyl, methoxy, ethoxy or phenoxy; B.sup.2 is hydrogen, methyl, ethyl, methoxy, ethoxy, chloro, bromo, C.sub.1 to C.sub.4 alkanoylamino or C.sub.1 to C.sub.4 alkoxycarbonylamino; R.sup.1 is C.sub.1 to C.sub.4 alkyl optionally bearing hydroxy, C.sub.1 to C.sub.4 alkoxy, C.sub.1 to C.sub.4 alkanoyloxy, C.sub.1 to C.sub.4 alkoxycarbonyl, C.sub.1 to C.sub.4 alkanoylamino or chloro as a substituent, cyclohexyl, phenylethyl, phenoxyethyl or a radical of the formula: ##STR6## A.sup.1 is a direct bond, --O--, --NH-- or ##STR7## A.sup.2 is a radical of the formula ##STR8##

or (when A.sup.1 is --NH-- or --O--) may also be --O--A.sup.5 ;

A.sup.3 is hydrogen, C.sub.1 to C.sub.8 alkyl optionally bearing hydroxy, C.sub.1 to C.sub.4 alkoxy, chloro, cyano, C.sub.1 to C.sub.4 alkoxycarbonyl, C.sub.1 to C.sub.4 alkanoylamino, C.sub.1 to C.sub.4 alkylaminocarbonyloxy, C.sub.1 to C.sub.4 alkoxycarbonyloxy or C.sub.1 to C.sub.4 alkanoyloxy as a substituent, allyl, cyclohexyl, benzyl, or phenyl optionally bearing chloro, bromo, methyl or C.sub.1 to C.sub.4 alkoxycarbonyl as a substituent; A.sup.4 is hydrogen or C.sub.1 to C.sub.4 alkyl optionally bearing hydroxy, chloro, C.sub.1 to C.sub.4 alkoxy or C.sub.1 to C.sub.4 alkanoyloxy as a substituent; A.sup.5 is C.sub.1 to C.sub.4 alkyl optionally bearing hydroxy, chloro, C.sub.1 to C.sub.4 alkoxy, C.sub.1 to C.sub.4 alkanoyloxy or C.sub.1 to C.sub.4 alkylaminocarbonyloxy as a substituent, cyclohexyl or phenyl; and Q is a radical of the formula ##STR9##

Examples of alkanoylamino radicals B.sup.2 are: butyrylamino, propionylamino, formylamino and particularly acetylamino and also NHCOOCH.sub.3, NHCOOC.sub.2 H.sub.5, NHCOOC.sub.3 H.sub.7 and NHCOOC.sub.4 H.sub.9.

Examples of radicals R.sup.1 other than those already specified are: C.sub.2 H.sub.4 OC.sub.3 H.sub.7, C.sub.2 H.sub.4 OC.sub.4 H.sub.9, C.sub.2 H.sub.4 OCOC.sub.4 H.sub.9, C.sub.2 H.sub.4 OCOC.sub.3 H.sub.7, C.sub.2 H.sub.4 OCOC.sub.2 H.sub.5, ##STR10## C.sub.2 H.sub.4 COOC.sub.4 H.sub.9, C.sub.3 H.sub.6 NHCOCH.sub.3, C.sub.2 H.sub.4 COOC.sub.3 H.sub.7, C.sub.2 H.sub.4 Cl, particularly CH.sub.3, C.sub.2 H.sub.5, C.sub.3 H.sub.7, C.sub.4 H.sub.9, C.sub.2 H.sub.4 OH, C.sub.2 H.sub.4 CN, CH.sub.2 CHOHCH.sub.3, C.sub.2 H.sub.4 OCH.sub.3, C.sub.2 H.sub.4 OC.sub.2 H.sub.5, C.sub.2 H.sub.4 OCOCH.sub.3, C.sub.2 H.sub.4 COOCH.sub.3 and C.sub.2 H.sub.4 COOC.sub.2 H.sub.5.

Examples of radicals Q--A.sup.1 --CO--A.sup.2 are: C.sub.2 H.sub.4 CONHCH.sub.3, C.sub.2 H.sub.4 CON(CH.sub.3).sub.2, C.sub.2 H.sub.4 CONHC.sub.2 H.sub.5, C.sub.2 H.sub.4 CON(C.sub.2 H.sub.5).sub.2, ##STR11## C.sub.2 H.sub.4 CONHC.sub.3 H.sub.7, C.sub.2 H.sub.4 CONHC.sub.4 H.sub.9, C.sub.2 H.sub.4 CON(C.sub.4 H.sub.9).sub.2, ##STR12## C.sub.2 H.sub.4 CONHC.sub.2 H.sub.4 CN, ##STR13## C.sub.2 H.sub.4 CONHC.sub.2 H.sub.4 OCH.sub.3, C.sub.2 H.sub.4 CONHC.sub.3 H.sub.6 OCH.sub.3, C.sub.2 H.sub.4 CONHC.sub.2 H.sub.4 OC.sub.2 H.sub.5, C.sub.2 H.sub.4 CONHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH, C.sub.2 H.sub.4 CONHC.sub.2 H.sub.4 OH, ##STR14## C.sub.2 H.sub.4 CON(C.sub.2 H.sub.4 OH).sub.2, C.sub.2 H.sub.4 CONHC.sub.3 H.sub.6 OH, C.sub.2 H.sub.4 CONHCH.sub.2 CHOHCH.sub.3, C.sub.2 H.sub.4 CONHC.sub.2 H.sub.4 OCOCH.sub.3, C.sub.2 H.sub.4 CONHC.sub.2 H.sub.4 OCOC.sub.3 H.sub.7, ##STR15## C.sub.2 H.sub.4 CONHC.sub.3 H.sub.6 OCOCH.sub.3, C.sub.2 H.sub.4 CONHC.sub.2 H.sub.4 OCONHCH.sub.3, C.sub.2 H.sub.4 CONHC.sub.2 H.sub.4 OCONHC.sub.4 H.sub.9, C.sub.2 H.sub.4 CONHC.sub.2 H.sub.4 OCOOCH.sub.3, C.sub.2 H.sub.4 CONHC.sub.2 H.sub.4 NHCOCH.sub.3, C.sub.2 H.sub.4 CONHC.sub.2 H.sub.4 NHCOC.sub.3 H.sub.7, C.sub.2 H.sub.4 OCONH.sub.2, C.sub.2 H.sub.4 OCONHCH.sub.3, ##STR16## C.sub.2 H.sub.4 OCON(CH.sub.3).sub.2, C.sub.2 H.sub.4 OCONHC.sub.2 H.sub.5, C.sub.2 H.sub.4 OCON(C.sub.2 H.sub.5).sub.2, C.sub.2 H.sub.4 OCONHCH.sub.2 -CH.dbd.CH.sub.2, C.sub.2 H.sub.4 OCONHC.sub.3 H.sub.7, C.sub.2 H.sub.4 OCONHC.sub.4 H.sub.9, C.sub.2 H.sub.4 OCON(C.sub.4 H.sub.9).sub.2, C.sub.2 H.sub.4 OCONHC.sub.5 H.sub.11, C.sub.2 H.sub.4 OCONH(CH.sub.2).sub.5 CN, C.sub.2 H.sub.4 OCONHC.sub.6 H.sub.13, C.sub.2 H.sub.4 OCONHC.sub.7 H.sub.15, C.sub.2 H.sub.4 OCONHC.sub.8 H.sub.17, ##STR17## C.sub.2 H.sub.4 OCONHCH.sub.2 COOCH.sub.3, C.sub.2 H.sub.4 OCONHCH.sub.2 COOC.sub.2 H.sub.5, C.sub.2 H.sub.4 OCONH(CH.sub.2).sub.2 COOCH.sub.3, C.sub.2 H.sub.4 OCONH(CH.sub.2).sub.3 COOCH.sub.3, C.sub.2 H.sub.4 OCONHC.sub.2 H.sub.4 Cl, C.sub.2 H.sub.4 OCONHC.sub.2 H.sub.4 OCOCH.sub.3, C.sub.2 H.sub.4 OCONHC.sub.2 H.sub.4 OH, C.sub.2 H.sub.4 OCONHC.sub.3 H.sub.6 OH, C.sub.2 H.sub.4 OCONHC.sub.2 H.sub.4 CN, C.sub.2 H.sub.4 OCON(C.sub.2 H.sub.4 CN).sub.2, ##STR18## C.sub.2 H.sub.4 OCOOC.sub.2 H.sub.4 OCH.sub.3, C.sub.2 H.sub.4 OCOOC.sub.3 H.sub.6 OCH.sub.3, C.sub.2 H.sub.4 OCOOC.sub.2 H.sub.4 OC.sub.2 H.sub.5, CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCOOCH.sub.3, C.sub.2 H.sub.4 OCOOC.sub.2 H.sub.4 Cl, ##STR19## C.sub.3 H.sub.6 NHCON(CH.sub.3).sub.2, C.sub.3 H.sub.6 NHCONHC.sub.2 H.sub.5, C.sub.3 H.sub.6 NHCON(C.sub.2 H.sub.5).sub.2, C.sub.3 H.sub.6 NHCONHC.sub.3 H.sub.7, C.sub.3 H.sub.6 NHCONHC.sub.4 H.sub.9, C.sub.2 H.sub.4 NHCONHC.sub.4 H.sub.9, C.sub.3 H.sub.6 NHCONHC.sub.6 H.sub.13, ##STR20## C.sub.3 H.sub.6 NHCONHCH.sub.2 COOCH.sub.3, C.sub.3 H.sub.6 NHCONHCH.sub.2 COOCH.sub.2 H.sub.5, C.sub.3 H.sub.6 NHCONH(CH.sub.2).sub.2 COOCH.sub.3, C.sub.3 H.sub.6 NHCONHC.sub.2 H.sub.4 CN, ##STR21## C.sub.3 H.sub.6 NHCOOC.sub.2 H.sub.4 OCH.sub.3, C.sub.3 H.sub.6 NHCOOC.sub.2 H.sub.4 OC.sub.2 H.sub.5, C.sub.3 H.sub.6 NHCOOC.sub.3 H.sub.6 OCH.sub.3, C.sub.3 H.sub.6 NHCOOC.sub.2 H.sub.4 Cl, C.sub.2 H.sub.4 NHCOOC.sub.2 H.sub.4 OH, C.sub.3 H.sub.6 NHCOOC.sub.2 H.sub.4 OH, C.sub.3 H.sub.6 NHCOOC.sub.3 H.sub.6 OH, C.sub.3 H.sub.6 NHCOOC.sub.2 H.sub.4 OCOCH.sub.3, C.sub.3 H.sub.6 NHCOOC.sub.2 H.sub.4 OCONHCH.sub.3, ##STR22##

Dyes of the formula (Ia): ##STR23## in which D.sup.1 is 5-nitrobenzoisothiazolyl-(2,1), 5-nitro-7-bromobenzoisothiazolyl-(2,1), 7-nitrobenzoisothiazolyl-(1,2), 5-bromo-7-nitrobenzoisothiazolyl-(1,2) or 5-cyano-7-nitrobenzoisothiazolyl-(1,2);

B.sup.3 is hydrogen, methoxy or ethoxy; B.sup.4 is hydrogen, chloro, methyl, acetylamino or propionylamino; and R.sup.2 is C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxyethyl, C.sub.1 to C.sub.4 alkoxypropyl, .beta.-cyanoethyl, .beta.-chloroethyl, .beta.-hydroxyethyl, .beta.-hydroxypropyl, .beta.-C.sub.1 to C.sub.4 alkanoyloxyethyl, .beta.-C.sub.1 to C.sub.4 alkanoyloxypropyl, C.sub.1 to C.sub.4 alkoxycarbonyl, phenylethyl or a radical of the formula ##STR24## in which A.sup.1 and A.sup.2 have the above meanings are of particular technical importance.

Examples of preferred radicals ##STR25## are: C.sub.2 H.sub.4 CONHCH.sub.3, C.sub.2 H.sub.4 CONHC.sub.2 H.sub.5, C.sub.2 H.sub.4 CONHC.sub.3 H.sub.7, C.sub.2 H.sub.4 CONHC.sub.4 H.sub.9, C.sub.2 H.sub.4 CONHC.sub.2 H.sub.4 OCH.sub.3, C.sub.2 H.sub.4 CONHC.sub.3 H.sub.6 OCH.sub.3, C.sub.2 H.sub.4 CONHC.sub.2 H.sub.4 OH, ##STR26## C.sub.2 H.sub.4 CONHC.sub.3 H.sub.6 OH, C.sub.2 H.sub.4 CONHCH.sub.2 CHOHCH.sub.3, C.sub.2 H.sub.4 CONHC.sub.2 H.sub.4 OCOCH.sub.3, C.sub.2 H.sub.4 NHC.sub.2 H.sub.4 OCOC.sub.3 H.sub.7, ##STR27## C.sub.2 H.sub.4 CONHC.sub.3 H.sub.6 OCOCH.sub.3, C.sub.2 H.sub.4 CONHC.sub.2 H.sub.4 OCONHCH.sub.3, C.sub.2 H.sub.4 CONHC.sub.2 H.sub.4 OCONHC.sub.4 H.sub.9, C.sub.2 H.sub.4 OCONHCH.sub.3, ##STR28## C.sub.2 H.sub.4 OCON(CH.sub.3).sub.2, C.sub.2 H.sub.4 OCON(C.sub.2 H.sub.5).sub.2, C.sub.2 H.sub.4 OCONHC.sub.3 H.sub.7, C.sub.2 H.sub.4 OCONHC.sub.4 H.sub.9, C.sub.2 H.sub.4 OCONHCH.sub.2 COOC.sub.2 H.sub.5, C.sub.2 H.sub.4 OCONHCH.sub.2 COOCH.sub.3, C.sub.2 H.sub.4 OCONHC.sub.2 H.sub.4 Cl, ##STR29## C.sub.2 H.sub.4 OCOOC.sub.2 H.sub.5, C.sub.2 H.sub.4 OCOOC.sub.3 H.sub.7, C.sub.2 H.sub.4 OCOOC.sub.4 H.sub.9, ##STR30## C.sub.2.sub.H.sub.4 OCOOC.sub.2 H.sub.4 OCH.sub.3, C.sub.2 H.sub.4 OCOOC.sub.3 H.sub.6 OCH.sub.3, C.sub.2 H.sub.4 OCOOC.sub.2 H.sub.4 Cl; C.sub.3 H.sub.6 NHCONHCH.sub.3, C.sub.3 H.sub.6 NHCON(CH.sub.3).sub.2, C.sub.3 H.sub.6 NHCON(C.sub.2 H.sub.5).sub.2, C.sub.3 H.sub.6 NHCONHC.sub.3 H.sub.7, C.sub.3 H.sub.6 NHCONHC.sub.4 H.sub.9, C.sub.3 H.sub.6 NHCONHCH.sub.2 COOC.sub.2 H.sub.5, ##STR31## C.sub.3 H.sub.6 NHCOOCH.sub.3, C.sub.3 H.sub.6 NHCOOC.sub.2 H.sub.5, C.sub.3 H.sub.6 NHCOOC.sub.3 H.sub.7, C.sub.3 H.sub.6 NHCOOC.sub.4 H.sub.9, ##STR32## C.sub.2 H.sub.4 OCOOC.sub.2 H.sub.4 OCH.sub.3, C.sub.2 H.sub.4 OCOOC.sub.3 H.sub.6 OCH.sub.3, C.sub.2 H.sub.4 OCOOC.sub.2 H.sub.4 OC.sub.2 H.sub.5, C.sub.3 H.sub.6 NHCOOC.sub.2 H.sub.4 Cl and C.sub.3 H.sub.6 NHCOOC.sub.2 H.sub.4 OH.

Particularly preferred meanings are:

D.sup.1 : 5-nitrobenzoisothiazolyl-(2,1), 7-nitrobenzoisothiazolyl-(1,2), 5-bromo-7-nitrobenzoisothiazolyl-(1,2) or 5-cyano-7-nitrobenzoisothiazolyl-(1,2); B.sup.3 : hydrogen; B.sup.4 : hydrogen, methyl or acetylamino; and R.sup.2 : methyl, ethyl, methoxyethyl, .beta.-cyanoethyl, .beta.-hydroxyethyl, or a radical of the formula ##STR33##

Particularly preferred radicals ##STR34## are:

C.sub.2 H.sub.4 CONHC.sub.2 H.sub.4 OH, ##STR35## C.sub.2 H.sub.4 CONHC.sub.3 H.sub.6 OH, C.sub.2 H.sub.4 CONHCH.sub.2 CHOHCH.sub.3, C.sub.2 H.sub.4 CONHC.sub.2 H.sub.4 OCOCH.sub.3, ##STR36## C.sub.2 H.sub.4 CONHC.sub.3 H.sub.6 OCOCH.sub.3, C.sub.2 H.sub.4 OCONHCH.sub.3, C.sub.2 H.sub.4 OCON(CH.sub.3).sub.2, C.sub.2 H.sub.4 OCONHC.sub.4 H.sub.9, C.sub.3 H.sub.6 NHCONHCH.sub.3, C.sub.3 H.sub.6 NHCONHC.sub.4 H.sub.9, C.sub.3 H.sub.6 NHCOOCH.sub.3 and C.sub.3 H.sub.6 NHCOOC.sub.2 H.sub.4 OH.

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

d--nh.sub.2 (ii) with a coupling component of the formula (III): ##STR37## where D, B.sup.1, B.sup.2, R.sup.1, A.sup.1 and A.sup.2 have the above meanings, the diazotization and coupling being carried out as usual.

Dyes of the formula (I) are red to greenish blue and are suitable for dyeing synthetic and cellulosic fibers and particularly cellulose esters and polyesters.

Dyeings are obtained which show deep shades and generally have very good wet and light fastness properties and also resistance to high temperatures. In the case of dyes suitable for cellulose esters the very good fastness to gas fume fading, dry cleaning and perspiration may be stressed and in the case of the polyester dyes fastness to thermofixation and fastness properties after thermofixation.

The following Examples illustrate the invention. In them the references to parts and percentages are by weight unless otherwise stated.

EXAMPLE 1

19.5 parts of 3-amino-5-nitro-2,1-benzoisothiazole is introduced into 100 parts of 85% sulfuric acid at from 10.degree. to 15.degree. C. 30 parts of nitrosylsulfuric acid (with a content of 13.1% of dinitrogen trioxide) is dripped into this solution at 0.degree. to 5.degree. C. The diazo solution obtained is stirred for another three hours at 0.degree. to 5.degree. C. and then dripped into a solution of 25 parts of N-ethyl-N-.beta.-[N'-methyl-N'-(.beta.-hydroxyethyl)]-carbamoyl-ethylaniline, 40 parts of 10% hydrochloric acid, 500 parts of water, 500 parts of ice and 1 part of sulfamic acid. The whole is then neutralized to pH 1.5 with sodium acetate solution, and the precipitated dye is suction filtered, washed with water until neutral and dried at subatmospheric pressure at 50.degree. C. 31 parts of the dye of the formula: ##STR38## is obtained; it gives on polyesters and preferentially on cellulose esters intense blue dyeings with good fastness properties and particularly good fastness to light, wet treatment and dry cleaning.

EXAMPLE 2

9.7 Parts of 4-amino-7-nitro-1,2-benzoisothiazole is introduced at 10.degree. to 15.degree. C. into 100 parts of 85% sulfuric acid. 15 parts of nitrosylsulfuric acid (with a content of 13.1% of dinitrogen trioxide) is dripped into this solution at from 0.degree. to 5.degree. C. The diazo solution obtained is stirred for another three hours at 0.degree. to 5.degree. C. and then dripped into a solution of 13.9 parts of N-ethyl-N-.beta.-(N'-.beta.-acetoxyethyl)-carbamoylethyl-aniline, 20 parts of 10% hydrochloric acid, 250 parts of water, 250 parts of ice and 1 part of sulfamic acid. Neutralization to pH 1.5 is then carried out with sodium acetate solution, the precipitated dye is suction filtered, washed with water until neutral and dried at subatmospheric pressure at 50.degree. C. 31 parts of the dye of the formula: ##STR39## is obtained which gives intense violet dyeings having good fastness properties on polyesters and cellulose esters.

EXAMPLE 3

19.5 Parts of 3-amino-5-nitro-2,1-benzoisothiazole is introduced at from 10.degree. to 15.degree. C. into 100 parts of 85% sulfuric acid. 30 parts of nitrosylsulfuric acid (having a content of 13.1% of dinitrogen trioxide) is dripped into this solution at 0.degree. to 5.degree. C. The diazo solution obtained is stirred for another three hours at from 0.degree. to 5.degree. C. and then dripped into a solution of 22.2 parts of N-ethyl-N-[.beta.-(methylaminocarbonyloxy)-ethyl]-aniline, 40 parts of 10% hydrochloric acid, 500 parts of water, 500 parts of ice and 1 part of sulfamic acid. The whole is then neutralized to pH 1 with sodium acetate solution. The precipitated dye is suction filtered, washed with water until it is neutral and dried at subatmospheric pressure at 50.degree. C. 32 parts of the dye of the formula: ##STR40## is obtained. It gives intense blue dyeings with good fastness properties on polyesters and cellulose esters.

EXAMPLE 4

19.5 Parts of 3-amino-5-nitro-2,1-benzoisothiazole is introduced at from 10.degree. to 15.degree. C. into 100 parts of 85% sulfuric acid. 30 parts of nitrosylsulfuric acid (13.1% of N.sub.2 O.sub.3) is dripped into this solution at from 0.degree. to 5.degree. C. The diazo solution obtained is stirred for 3 hours at from 0.degree. to 5.degree. C. and then dripped into a solution of 26.4 parts of N-ethyl-N-[.beta.-(n-butylaminocarbonyloxy)-ethyl]-aniline, 40 parts of 10% hydrochloric acid, 500 parts of water, 500 parts of ice and 1 part of sulfamic acid. The whole is then neutralized to pH 1.5 with sodium acetate. The precipitated dye is suction filtered, washed with water until it is neutral and dried at 50.degree. C. at subatmospheric pressure. 33 parts of the dye of the formula ##STR41## is obtained which gives intense blue dyeings with good fastness properties on polyesters.

EXAMPLE 5

13.7 Parts of 4-amino-5-bromo-7-nitro-1,2-benzoisothiazole is dissolved in 100 parts of 96% sulfuric acid at from 10.degree. to 15.degree. C. Then 30 parts of a mixture (17:3) of glacial acetic acid and propionic acid is gradually added to the solution at from 0.degree. to 5.degree. C. and diazotization is effected by dripping in 15 parts of nitrosylsulfuric acid (13.1% of N.sub.2 O.sub.3) at 0.degree. to 5.degree. C. The whole is stirred for another three hours at 0.degree. to 5.degree. C. and the diazo solution is run into a solution of 13.2 parts of N-ethyl-N-[.beta.-(n-butylcarbamoyloxy)ethyl]-aniline, 20 parts of 10% hydrochloric acid, 250 parts of water, 200 parts of ice and 1 part of sulfamic acid. The pH is adjusted to 1.5 with sodium acetate solution, and the precipitated dye is suction filtered, washed with water until it is neutral and dried at subatmospheric pressure at 50.degree. C. 22 parts of the dye of the formula: ##STR42## is obtained. It gives an intense reddish blue having good fastness properties on polyesters.

EXAMPLE 6

5.5 Parts of 4-amino-5-cyano-7-nitrobenzoisothiazole-(1,2) is introduced at 10.degree. C. into a mixture of acids consisting of 50 parts of 85% sulfuric acid and 15 parts of a mixture (17:3) of glacial acetic acid and propionic acid. 9.5 parts of nitrosylsulfuric acid (11.1% N.sub.2 O.sub.3) is added at from 0.degree. to 5.degree. C. and the mixture is stirred for four hours at this temperature. Excess nitrosylsulfuric acid is destroyed in the usual way. The diazo solution is added in portions to a solution, cooled to from 0.degree. to 5.degree. C., of 9.6 parts of N-ethyl-N-[-.beta.-(n-butylamino-carbonyloxy)-ethoxy]-m-toluidine in 100 parts by volume of glacial acetic acid and at the same time 250 parts of ice is introduced gradually. After the coupling is completed the dye is suction filtered, washed with water until it is neutral and dried at 50.degree. C. at subatmospheric pressure.

10.4 parts of the dye of the formula: ##STR43## is obtained. It gives very intense dyeings having outstanding fastness properties on polyesters.

EXAMPLE 7

19.5 Parts of 3-amino-5-nitro-2,1-benzoisothiazole is introduced at from 10.degree. to 15.degree. C. into 100 parts of 85% sulfuric acid. 30 parts of nitrosylsulfuric acid (having a content of 13.1% of dinitrogen trioxide) is dripped in at from 0.degree. to 5.degree. C. The diazo solution obtained is stirred at from 0.degree. to 5.degree. C. for three hours and then dripped into a solution of 26.6 parts of N-ethyl-N-(carbo-.beta.-oxyethoxyaminopropyl)-aniline, 40 parts of 10% hydrochloric acid, 500 parts of water, 500 parts of ice and 1 part of sulfamic acid. Then the pH is adjusted to 1 with sodium acetate solution. The precipitated dye is suction filtered, washed with water until it is neutral and dried at 50.degree. C. at subatmospheric pressure. 33 parts of the dye of the formula: ##STR44## is obtained. It gives intense blue dyeings having good fastness properties on polyesters and cellulose esters.

EXAMPLE 8

9.7 Parts of 4-amino-7-nitrobenzoisothiazole-(1,2) is introduced into 100 parts of 85% sulfuric acid at from 10.degree. to 15.degree. C. 15 parts of nitrosylsulfuric acid (with a content of 13.1% of dinitrogen trioxide) is dripped into this solution at from 0.degree. to 5.degree. C. The diazo solution obtained is stirred for another 3 hours at 0.degree. to 5.degree. C. and then dripped into a solution of 14.0 parts of N-ethyl-N-(carbo-.beta.-oxyethoxy-aminopropyl)-m-toluidine, 40 parts of 10% hydrochloric acid, 500 parts of water, 500 parts of ice and 1 part of sulfamic acid. The pH is then adjusted to 1 with sodium acetate solution. The precipitated dye is suction filtered, washed with water until it is neutral and dried at 50.degree. C. at subatmospheric pressure. 34 parts of the dye of the formula: ##STR45## is obtained. It gives intense violet dyeings on polyesters and cellulose esters.

EXAMPLE 9

5.5 Parts of 4-amino-5-cyano-7-nitrobenzoisothiazole-(1,2) is introduced at 10.degree. C. into a mixture of acids consisting of 50 parts of 85% sulfuric acid and 15 parts by volume of a mixture (17:3) of glacial acetic acid and propionic acid. 9.5 parts of nitrosylsulfuric acid (11.1% of N.sub.2 O.sub.3) is added at from 0.degree. to 5.degree. C. and the mixture is stirred for four hours at this temperature. The excess of nitrosylsulfuric acid is destroyed as usual. The diazo solution is added in portions to a solution, cooled to 0.degree. to 5.degree. C., of 5.5 parts of N-ethyl-N-[.gamma.-(methoxycarbonylamino)-propyl-]aniline in 100 parts by volume of glacial acetic acid and 250 parts of ice is gradually added at the same time. When the coupling has been completed the dye is suction filtered, washed with water until it is neutral and dried at 50.degree. C. at subatmospheric pressure. 8.7 parts of the dye of the formula: ##STR46## is obtained. It dyes polyesters full blue hues having good fastness properties.

EXAMPLE 10

5.5 parts of 4-amino-5-cyano-7-nitrobenzoisothiazole is introduced at 10.degree. C. into a mixture of acids consisting of 50 parts 85% sulfuric acid and 15 parts by volume of a mixture (17:3) of glacial acetic acid and propionic acid. 9.5 parts of nitrosylsulfuric acid (M = 342) is added thereto at from 0.degree. to 5.degree. C. and the mixture is stirred for 4 hours at this temperature. The excess of nitrosylsulfuric acid is destroyed in the usual way. The diazo solution is added in portions to a solution, cooled to 0.degree. to 5.degree. C., of 6.9 parts of N-ethyl-N-[.gamma.-(n-butylaminocarbonylamino)-propyl]-aniline in 100 parts by volume of glacial acetic acid and at the same time 250 parts of ice is gradually introduced. After the coupling is ended the dye is suction filtered, washed with water to make it neutral and dried at 50 .degree. C. at subatmospheric pressure. 9.8 parts of the dye of the formula: ##STR47## is obtained. It gives intense blue dyeings having good fastness properties on polyesters.

Dyes of the formula (I) which are hereinafter characterized by specifying their substituents are also obtained by methods analogous to those described in Examples 1 to 10.

No. DK B.sup.1 B.sup.2 R.sup.1 alkylene A.sup.1 A.sup.2 Hue 11 ##STR48## H H C.sub.2 H.sub.4 OH C.sub.2 H.sub.4 -- NHCH.sub.3 blue 12 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 -- NHC.sub.2 H.sub.4 OH " 13 " H H CH.sub.2 CHOHCH.sub.2 Cl C.sub.2 H.sub.4 -- NHC.sub.2 H.sub.4 OH " 14 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 -- NHC.sub.3 H.sub.6 OH " 15 " H H C.sub.2 H.sub.5 C.sub.2 44 -- NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH " 16 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 -- NHCH.sub.2 CHOHCH.sub.3 " 17 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 -- ##STR49## " 18 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 -- NHC.sub.2 H.sub.4 OCOCH.sub.3 " 19 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 -- NHC.sub.2 H.sub.4 NHCOCH.sub.3 " 20 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.4 O NHCH.sub.3 " 21 " H CH.sub.3 CH.sub.3 C.sub.2 H.sub.4 O NHCH.sub.3 " 22 " H H C.sub.2 H.sub.4 OCH.sub.3C.sub.2 H.sub.4 O NHCH.sub.3 " 23 " H NHCOCH.sub.3 C.sub.2 H.sub.4 OCONHCH.sub.3 C.sub.2 H.sub.4 O NHCH.sub.3 greenish blue 24 " H H C.sub.2 H.sub.4 COOCH.sub.3 C.sub.2 H.sub.4 O NHCH.sub.3 blue 25 " H CH.sub.3 C.sub.2 H.sub.4 OCONHCH.sub.3 C.sub.2 H.sub.4 O NHCH.sub.3 " 26 " H H C.sub.2 H.sub.5 ##STR50## O NHCH.sub.3 " 27 " H H C.sub.2 H.sub.5 ##STR51## O NHCH.sub.3 " 28 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 O N(CH.sub.3).sub.2 " 29 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 O NHCH.sub.2 COOC.sub.2 H.sub.5 " 30 " H H C.sub.2 H.sub.4 OCOCH.sub.3 C.sub.2 H.sub.4 O NHC.sub.2 H.sub.4 Cl " 31 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 O NHC.sub.2 H.sub.4 OH " 32 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 O ##STR52## " 33 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.4 O NHC.sub.4 H.sub.9 " 34 " H CH.sub.3 CH.sub.3 C.sub.2 H.sub.4 O NHC.sub.4 H.sub.9 " 35 " OCH.sub.3 NHCOCH.sub.3 C.sub.2 H.sub.4 CN C.sub.2 H.sub.4 O NHC.sub.4 H.sub.9 greenish blue 36 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.4 O NH(CH.sub.2).sub.5 CN blue 37 " H H C.sub.2 H.sub.4 CN C.sub.2 H.sub.4 O OCH.sub.3 bluish violet 38 " H H C.sub.2 H.sub.4 OCOOCH.sub.3 C.sub.2 H.sub.4 O OCH.sub.3 " 39 " H H C.sub.2 H.sub.4 OC.sub.2 H.sub.5 C.sub.2 H.sub.4 O OC.sub.2 H.sub.4 Cl " 40 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 O OC.sub.4 H.sub.9 " 41 " H H C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH NHCH.sub.3 blue 42 " H H C.sub.2 H.sub.5 C.sub.3 H.sub.6 NC.sub.2 H.sub.4 CN NHC.sub.4 H.sub.9 " 43 " H H C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH N(CH.sub.3).sub.2 " 44 " H H C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH ##STR53## " 45 " H H C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH OCH.sub.3 " 46 " H H CH.sub.3 C.sub.3 H.sub.6 NH OCH.sub.3 " 47 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH OC.sub.2 H.sub.4 OH " 48 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 NH OC.sub.2 H.sub.4 OH " 49 " H H C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH OC.sub.2 H.sub.4 OCOCH.sub.3 " 50 " H H C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH ##STR54## " 51 ##STR55## H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 -- NHC.sub.2 H.sub.4 OCOCH.sub.3 greenish blue 52 " H H C.sub.4 H.sub.9 C.sub.2 H.sub.4 -- NHC.sub.2 H.sub.4 OCONHCH.sub.3 " 53 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 -- NHC.sub.2 H.sub.4 OCH.sub.3 " 54 " H H C.sub.2 H.sub.5 ##STR56## O NHCH.sub.3 " 55 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 O NHC.sub.4 H.sub.9 " 56 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 O NH(C.sub.4 H.sub.9).sub.2 " 57 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 O NHCH.sub.2 COOC.sub.2 H.sub.5 " 58 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 O NHCH.sub.2CHCH.sub.2 " 59 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 O ##STR57## " 60 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 O OCH.sub.3 " 61 " H H ##STR58## C.sub.2 H.sub.4 O OCH.sub.3 " 62 " H H C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH NHC.sub.4 H.sub.9 " 63 " H H C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH ##STR59## " 64 " H H C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH NHCH.sub.3 " 65 " H H C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH OC.sub.2 H.sub.4 OH " 66 " H CH.sub.3 CH.sub.3 C.sub.3 H.sub.6 NH OC.sub.2 H.sub.4 OH " 67 " H H C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH OC.sub.2 H.sub.4 OCONHC.sub.4 H.sub.9 " 68 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH ##STR60## " 69 ##STR61## H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 -- ##STR62## " 70 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.4 O NHC.sub.4 H.sub.9 " 71 " H H C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH OC.sub.2 H.sub.4 OH " 72 ##STR63## H H C.sub.2 H.sub.4 OH C.sub.2 H.sub.4 -- NHC.sub.2 H.sub.4 NHCOC.sub.3 H.sub.7 violet 73 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 O NHC.sub.4 H.sub.9 " 74 " H H C.sub.2 H.sub.5 ##STR64## O ##STR65## " 75 ##STR66## H H C.sub.2 H.sub.4 Cl C.sub.2 H.sub.4 -- NHC.sub.3 H.sub.7 (n) " 76 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 O NHC.sub.3 H.sub.7 (i) " 77 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 O ##STR67## " 78 " H H C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH NHC.sub.2 H.sub.4 Cl" 79 ##STR68## H H C.sub.2 H.sub.4 OCOC.sub.3 H.sub.7 C.sub.2 H.sub.4 -- NHC.sub.4 H.sub.9 " 80 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 -- NHC.sub.2 H.sub.4 OH " 81 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 -- NHC.sub.3 H.sub.6 OCOCH.sub.3 " 82 " H H C.sub.2 H.sub.5 CH.sub.2 -- ##STR69## " 83 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 -- NHC.sub.2 H.sub.4 OCOC.sub.3 H.sub.7 " 84 " H H C.sub.2 H.sub.5 ##STR70## O NHCH.sub.3 " 85 " H HNCOCH.sub.3 C.sub.2 H.sub.4 OCONHCH.sub.3 C.sub.2 H.sub.4 O NHCH.sub.3 bluish violet 86 " H H C.sub.2 H.sub.4 COOC.sub.4 H.sub.9 C.sub.2 H.sub.4 O NHCH.sub.3 violet 87 " H H C.sub.2 H.sub.4 CN C.sub.2 H.sub.4 O NHCH.sub.3 reddish violet 88 " H Cl C.sub.2 H.sub.4 OCONHCH.sub.3 C.sub.2 H.sub.4 O NHCH.sub.3 " 89 " OC.sub.2 H.sub.5 NHCOCH.sub.3 C.sub.2 H.sub.4 OCONHCH.sub.3 C.sub.2 H.sub.4 O NHCH.sub.3 bluish violet 90 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 O N(CH.sub.3).sub.2 violet91 " H H ##STR71## C.sub.2 H.sub.4 O ##STR72## " 92 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 O OC.sub.4 H.sub.9 " 93 " H NHCOCH.sub.3 C.sub.2 H.sub.4 OCOOC.sub.2 H.sub.5 C.sub.2 H.sub.4 O OC.sub.2 H.sub.5 bluish violet 94 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 O ##STR73## violet 95 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH NHCH.sub.3 " 96 " H CH.sub.3 C.sub.3 H.sub.6 NHCOCH.sub.3 C.sub.3 H.sub.6 NH NHCH.sub.3 " 97 " H H C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH N(C.sub.4 H.sub.9).sub.2 " 98 " H H C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH OCH.sub.3 " 99 " H H C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH OC.sub.2 H.sub.4 OH" 100 " H H C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH OC.sub.2 H.sub.4 OCONHCH.sub.3 " 101 ##STR74## H H C.sub.3 H.sub.7 C.sub.2 H.sub.4 -- NHC.sub.2 H.sub.4 OCOCH.sub.3 bluish violet 102 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 O NH.sub.2 " 103 " H NHCOCH.sub.3 C.sub.2 H.sub.4 OCONHC.sub.4 H.sub.9 C.sub.2 H.sub.4 O NHC.sub.4 H.sub.9 blue 104 " H C.sub.2 H.sub.5 CH.sub.3 C.sub.2 H.sub.4 O ##STR75## bluish violet 105 " H H C.sub.2 H.sub.5 ##STR76## O OCH.sub.3 " 106 " H H C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH NHC.sub.4 H.sub.9 " 107 " H H C.sub.4 H.sub.9 C.sub.3 H.sub.6 NH ##STR77## " 108 ##STR78## H H C.sub.2 H.sub.4 OCOC.sub.3 H.sub.7 C.sub.2 H.sub.4 -- N(CH.sub.3).sub.2 " 109 " H H ##STR79## C.sub.2 H.sub. 4 -- NHC.sub.2 H.sub.5 " 110 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 -- NHC.sub.3 H.sub.6 OCOCH.sub.3 " 111 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 -- NHC.sub.2 H.sub.4 OCOC.sub.3 H.sub.7 " 112 " H H C.sub.2 H.sub.4 OCONHCH.sub.3 C.sub.2 H.sub.4 -- NHC.sub.2 H.sub.4 OCONHCH.sub.3 " 113 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 -- NHC.sub.2 H.sub.4 OCOOCH.sub.3 " 114 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.4 O NHCH.sub.3 " 115 ##STR80## H H ##STR81## ##STR82## O NHCH.sub.3 " 116 " CH.sub.3 H C.sub.2 H.sub.4 OCONHCH.sub.3 C.sub.2 H.sub.4 O NHCH.sub.3 " 117 " H H C.sub.2 H.sub.5 ##STR83## O NHCH.sub.3 " 118 " H NHCHO C.sub.2 H.sub.4 OCONHC.sub.4 H.sub.9 C.sub.2 H.sub.4 O NHC.sub.4 H.sub.9 blue 119 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 O NHC.sub.6 H.sub.13 bluish violet 120 " H H C.sub.2 H.sub.5 ##STR84## O OCH.sub.3 " 121 " ##STR85## NHCOCH.sub.3 C.sub.2 H.sub.4 CN C.sub.2 H.sub.4 OOCH.sub.3 blue 122 " H H CH.sub.2 CHOHCH.sub.3 ##STR86## O OC.sub.2 H.sub.4 Cl bluish violet 123 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.4 O OC.sub.2 H.sub.4 OCH.sub.3 " 124 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH NHC.sub.4 H.sub.9 blue 125 " H H C.sub.2 H.sub.5 C.sub.3 H.sub.6 NC.sub.2 H.sub.4 CN NHCH.sub.3 " 126 " H CH.sub.3 C.sub.3 H.sub.6 NHCONHCH.sub.3 C.sub.3 H.sub.6 NH NHCH.sub.3 " 127 " H H C.sub.2 H.sub.4 OCH.sub.3 C.sub.3 H.sub.6 NH ##STR87## " 128 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH OC.sub.2 H.sub.4 OH " 129 " H H C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH OC.sub.2 H.sub.4 OCOCH.sub.3 " 130 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH OC.sub.4 H.sub.9 " 131 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH OC.sub.2 H.sub.4 Cl " 132 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH OCH.sub.3 " 133 ##STR88## H H C.sub.2 H.sub.4 OCONHCH.sub.3 C.sub.2 H.sub.4 -- NHC.sub.2 H.sub.5 " 134 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.4 -- NHC.sub.2 H.sub.4 OCOCH.sub.3 " 135 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.4 -- NHC.sub.2 H.sub.4 OCOC.sub.3 H.sub.7 " 136 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.4 -- NHC.sub.2 H.sub.4 NHCOC.sub.3 H.sub.7 " 137 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.4 -- ##STR89## " 138 " H CH.sub.3C.sub.2 H.sub.5 C.sub.2 H.sub.4 O NHCH.sub.3 " 139 " H NHCOC.sub.3 H.sub.7 C.sub.2 H.sub.4 OCONHCH.sub.3 C.sub.2 H.sub.4 O NHCH.sub.3 greenish blue 140 " H H C.sub.2 H.sub.5 ##STR90## O NHCH.sub.3 blue 141 " C.sub.2 H.sub.5 H C.sub.2 H.sub.4 OH C.sub.2 H.sub.4 O NHCH.sub.3 " 142 " H CH.sub.3 C.sub.2 H.sub.5 ##STR91## O NHCH.sub.3 " 143 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.4 O NHC.sub.3 H.sub.7 (i) " 144 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.4 O NHC.sub.2 H.sub.4 CN " 145 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.4 O N(C.sub.2 H.sub.4 Cl).sub.2 " 146 " H CH.sub.3 CH.sub.2 CHOHCH.sub.3 ##STR92## O NHC.sub.4 H.sub.9 " 147 " H H C.sub.3 H.sub.7 C.sub.2 H.sub.4 O NHC.sub.4 H.sub.9 " 148 " H CH.sub.3 ##STR93## C.sub.2 H.sub.4 ONHC.sub.4 H.sub.9 " 149 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 O ##STR94## " 150 " H CH.sub.3 C.sub.2 H.sub. 5 C.sub.2 H.sub.4 O OCH.sub.3 " 151 " H H ##STR95## C.sub.2 H.sub.4 O OC.sub.3 H.sub.7 " 152 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.4 O OC.sub.3 H.sub.6 OCH.sub.3 " 153 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH NHCH.sub.3 greenish blue 154 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH NHC.sub.4 H.sub.9 " 155 " H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 NH NHC.sub.4 H.sub.9 blue 156 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH ##STR96## greenish blue 157 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH NHC.sub.6 H.sub.13 " 158 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH OCH.sub.3 " 159 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH OC.sub.2 H.sub.5 " 160 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH ##STR97## " 161 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH OC.sub.2 H.sub.4 OH " 162 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.3 H.sub.6 NH OC.sub.2 H.sub.4 OCH.sub.3 " 163 ##STR98## H H C.sub.2 H.sub.5 C.sub.2 H.sub.4 O NHC.sub.2 H.sub.5 blue 164 " H H C.sub.2 H.sub.4 CN C.sub.2 H.sub.4 O NHC.sub.4 H.sub.9 " 165 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.4 -- ##STR99## " 166 " H CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.4 -- NHC.sub.2 H.sub.4 OH "

Claims

1. A dye having the formula ##STR100## in which: D.sup.1 is 5-nitrobenzoisothiazolyl-(2,1), or

5-cyano-7-nitrobenzoisothiazolyl-(1,2);

B.sup.4 is hydrogen or methyl;

R.sup.2 is C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxyethyl, .beta.-cyanoethyl or .beta.-hydroxyethyl;

A.sup.1 is a direct bond, --NH-- or --O--;

A.sup.2 is NH--(C.sub.1 to C.sub.4)-alkyl, NH--C.sub.2 H.sub.4 OH, NH--C.sub.3 H.sub.6 OH, or ##STR101## or, when A.sup.1 is --NH-- or --O--, is OCH.sub.3, OC.sub.2 H.sub.5 or OC.sub.2 H.sub.4 OH; and

Q is --C.sub.2 H.sub.4 --, --C.sub.3 H.sub.6 -- or --C.sub.4 H.sub.8 --.

2. The dye having the formula: ##STR102##

3. The dye having the formula: ##STR103##

4. The dye having the formula: ##STR104##

5. The dye having the formula: ##STR105##

6. The dye having the formula: ##STR106##

7. The dye having the formula: ##STR107##

8. The dye having the formula: ##STR108##