Sulfo-containing halophenylazodiamino, cyano pyridine compounds

Abstract

Compounds useful for dyeing nylon, wool, and leather, having the formula: ##STR1## wherein X.sup.1 is chlorine, bromine, methyl or trifluoromethyl, Y.sup.3 is chlorine or bromine, and K.sup.1 is a radical of the formula ##STR2## where R.sup.3 is C.sub.2 to C.sub.4 hydroxyalkyl, methoxyethyl or methoxypropyl.

Description

The present invention relates to compounds which, in the form of the free acids, are of the general formula I ##STR3## where X is fluorine, chlorine, bromine, methyl, trifluoromethyl, C.sub.1 -C.sub.4 -alkylsulfonyl, arylsulfonyl, acetyl or benzoyl, Y is hydrogen, fluorine, chlorine, bromine, sulfamyl, C.sub.1 -C.sub.4 -mono- or -dialkylsulfamyl, C.sub.1 -C.sub.4 -alkylsulfonyl, methyl or trifluoromethyl, Y.sup.1 is hydrogen, hydroxysulfonyl, methyl or chlorine, Y.sup.2 is hydrogen or hydroxysulfonyl and K is a radical of the formula ##STR4## either Y.sup.1 or Y.sup.2 being hydroxysulfonyl, and T is cyano or methylsulfonyl, R is hydrogen or C.sub.1 -C.sub.3 -alkyl, R.sup.1 is hydrogen or alkyl or is benzyl, sulfobenzyl, phenylethyl, sulfophenylethyl, sulfophenylpropyl or C.sub.1 -C.sub.10 -alkyl which is unsubstituted or substituted by hydroxyl, cyano, C.sub.1 -C.sub.4 -alkanoyloxy or C.sub.1 -C.sub.8 -alkoxy, or is a radical of the formula ##STR5## R.sup.2 is hydrogen or C.sub.1 -C.sub.8 -alkyl, R.sup.3 is hydrogen or allyl, or is C.sub.1 -C.sub.10 -alkyl which may or may not be interrupted by oxygen and is unsubstituted or substituted by hydroxyl, cyano, C.sub.1 -C.sub.4 -alkanoyloxy, C.sub.1 -C.sub.8 -alkoxy, cyclohexyloxy, phenyl, phenoxy, sulfophenoxy, sulfophenyl or hydroxysulfonyloxy, or is cyclopentyl, or is cyclohexyl which is unsubstituted or substituted by hydroxyl, hydroxyethoxy or methyl, or is pyrrolidonylalkyl, phenyl, methoxyphenyl, sulfophenyl, C.sub.1 -C.sub.4 -alkoxysulfophenyl or a radical of the formula ##STR6## or R.sup.2 and R.sup.3, together with the nitrogen, form a saturated 5-membered or 6-membered ring, Z is phenyl which is unsubstituted or substituted by chlorine, methyl, methoxy or acetylamino, and A is a C.sub.2 -C.sub.10 -alkyl radical which may or may not be interrupted by oxygen.

Radicals R are, in addition to hydrogen, ethyl, propyl or, preferably, methyl. In addition to those already mentioned, specific examples of radicals R.sup.1, R.sup.2 and R.sup.3 (where these fall under the general definition) are:

1. Unsubstituted or substituted alkyl radicals: ##STR7##

2. unsubstituted or substituted cycloalkyl radicals ##STR8##

3. Aralkyl radicals: ##STR9## and those containing C.sub.6 H.sub.4 CH.sub.3 instead of C.sub.6 H.sub.5.

4. Sulfophenyl radicals: ##STR10##

5. ##STR11## where n is 2, 3, 4 or 6, C.sub.2 H.sub.4 OCHO, C.sub.2 H.sub.4 OCOC.sub.2 H.sub.5, C.sub.2 H.sub.4 OCOCH.sub.3, (C.sub.2 H.sub.4 O).sub.2 COCH.sub.3, (C.sub.2 H.sub.4 O).sub.2 CHO, (CH.sub.2).sub.3 OCOCH.sub.3, C.sub.3 H.sub.6 OCOC.sub.2 H.sub.5 and (CH.sub.2).sub.3 OCHO.

Examples of preferred substituents R.sup.1 and R.sup.3 are: ##STR12##

Within the scope of the general definitions, specific examples of radicals X and Y, in addition to those stated above, are methyl, ethyl, butyl, phenyl, tolylsulfonyl and the radicals of the formulae SO.sub.2 NHCH.sub.3, SO.sub.2 NHC.sub.2 H.sub.5, SO.sub.2 NHC.sub.3 H.sub.7, SO.sub.2 NHC.sub.4 H.sub.9, SO.sub.2 N(CH.sub.3).sub.2, SO.sub.2 N(C.sub.2 H.sub.5).sub.2, SO.sub.2 N(C.sub.3 H.sub.7).sub.2 or SO.sub.2 N(C.sub.4 H.sub.9).sub.2.

The dyes according to the invention can be prepared by diazotizing a diazo component of an amine of the formula ##STR13## by a conventional method, and reacting the resulting diazonium salt with a coupling component of the formula H--K.

Of particular importance are compounds of formula Ia ##STR14## where X.sup.1 is chlorine, bromine, methyl or trifluoromethyl, and K.sup.1 is a radical of the formula ##STR15## where R.sup.3 has the stated meanings.

Other useful compounds are those of the formula Ib ##STR16## where K.sup.1, X.sup.1 and Y.sup.3 have the meanings given in the case of formula Ia.

Dyes of the formula Ia which possess only one sulfo group are particularly suitable for producing level dyeings on nylon. Because of their fast rate of dyeing, they are particularly suitable for trichromatic dyeing.

The good lightfastness on wool, the advantageous phototropic behavior and the very good levelness are also noteworthy.

Some compounds according to the invention are also useful for dyeing leather.

In the Examples which follow, parts and percentages are by weight, unless stated otherwise.

PREPARATION OF THE INTERMEDIATES

(A) 2,4-Dichloroacetanilide

396 parts by volume of sulfuryl chloride are added to 270 parts of acetanilide in 1000 parts by volume of nitrobenzene in the course of 3 hours at from 50.degree. to 70.degree. C. (the chlorination is begun at a low temperature, which is then increased in order to suppress the precipitation of 2,4-dichloroacetanilide). When the addition of sulfuryl chloride is complete, stirring is continued for 1 hour from 70.degree. to 75.degree. C., after which dissolved hydrogen chloride is blown out with nitrogen. The mixture is then left to cool, whereupon 2,4-dichloroacetanilide is precipitated, and is isolated by being filtered off.

The product can be washed with water and dried to give 330 parts of 2,4-dichloroacetanilide, which contains about 5% of 2,4,6-trichloroacetanilide. If the nitrobenzene which is recovered as a filtrate, and in which some 2,4-dichloroacetanilide is still dissolved, is employed in a second experiment, the yield increases to 396 parts.

(B) 2,4-Dichloroaniline-6-sulfonic acid

204 parts of the crude 2,4-dichloroacetanilide are added to 300 parts of 100% strength sulfuric acid, while stirring. Thereafter, the mixture is heated further to 130.degree. C., and 235 parts of chlorosulfonic acid are added dropwise at this temperature in such a manner that the hydrogen chloride gas liberated can readily be removed. Stirring is then continued at from 135.degree. to 140.degree. C. until the sulfonation is complete, this taking about 1 hour. The mixture is then left to cool to 50.degree.-80.degree. C., and is poured into 1300 parts by volume of water. After steam distillation for a short time, 10 parts of pure 2,4,6-trichloroaniline are obtained, as a by-product, in the distillate. The reaction mixture is then cooled to room temperature, and precipitated 2,4-dichloroaniline-6-sulfonic acid is filtered off and washed with dilute hydrochloric acid. 204 parts of 2,4-dichloroaniline-6-sulfonic acid (calculated as 100% pure) are obtained as a colorless aqueous paste, which can be used in moist form for diazotizations. H-NMR in D.sub.2 O: 7.3 ppm, 7.6 ppm, J: 3 Hz (as the ammonium salt).

(C) 2,4-Dichloroaniline-5-sulfonic acid

204 parts of crude 2,4-dichloroacetanilide are carefully added to 600 parts of 23% strength oleum, and the mixture is heated to 140.degree. C. and stirred at this temperature for 1 hour. It is then left to cool to 50.degree.-80.degree. C. and is poured into 1000 parts of water. 10 parts of 2,4,6-trichloroaniline are isolated by steam distillation, and the remaining mixture is filtered after it has cooled. The gray product isolated is stirred with about 5000 parts of water and neutralized with sodium hydroxide solution. A little active carbon is added, after which the mixture is heated to about 95.degree. C. and filtered, and the resulting 2,4-dichloroaniline-5-sulfonic acid is precipitated from the filtrate by acidification and is isolated in a conventional manner after the mixture has cooled. The product still contains a small amount of 2,4-dichloroaniline-6-sulfonic acid, which can be removed by recrystallization from water. 2,4-Dichloroaniline-5-sulfonic acid is obtained as a colorless powder. Yield: about 140 parts. H-NMR in D.sub.2 O: 7.45 ppm (as the ammonium salt).

EXAMPLE 1

19.5 parts of 2,4-dichloroaniline-6-sulfonic acid are dissolved in 200 parts by volume of hot water at pH 7.5-10, using sodium hydroxide solution. A wetting agent which is effective under acidic conditions and 27 parts by volume of a 23% strength aqueous sodium nitrite solution are added, and the mixture is cooled to 0.degree.-5.degree. C. 60 parts of ice are added, after which 55 parts of a 15-18% strength hydrochloric acid solution are introduced all at once, and the mixture is stirred for a further 3 hours at from 0.degree. to 5.degree. C. Thereafter, a solution or suspension of 21.2 parts of 2,6-bis-(3-hydroxypropylamino)-3-cyano-4-methylpyridine in 120 parts by volume of water and 7 parts by volume of concentrated hydrochloric acid is run in, stirring is continued for from 15 to 30 minutes, and the pH of the mixture is then slowly increased to 2-2.5 by adding sodium hydroxide solution or sodium formate. The acid formed as a result of the coupling reaction is then bound continuously by adding appropriate amounts of sodium hydroxide solution or sodium formate. When the reaction has been maintained at pH 2-2.5 for about 30-60 minutes, the pH of the mixture is increased to 3-3.5 by adding dilute sodium hydroxide solution or sodium acetate, and stirring is continued at this pH until the coupling is substantially complete. The pH of the mixture is then increased to 4.3-4.7 by adding dilute sodium hydroxide solution, after which the coupling reaction quickly ends. The resulting dye of the formula ##STR17## is precipitated virtually quantitatively by adding 80 parts of sodium chloride, and is then isolated by filtration. It is dried to give 42 parts of a reddish brown powder which still contains about 1 part of water-soluble salts in addition to 41 parts of the dye.

The dye dissolves in water to give a yellow solution and dyes nylon and wool in intense, lightfast, golden yellow hues. The absorption maximum of a solution of about 0.020 part of dye in 900 parts by volume of dimethylformamide and 150 parts by volume of glacial acetic acid is 427.5 nm.

The particular advantage of this dye is the high migrating power and the ability to dye nylon simultaneously with red and blue dyes. For example, a dye mixture of about 4 parts of this dye with about 4 parts of Acid Red 57 and 3 parts of Acid Blue 72 gives a (dark) brown. All three dyes dye nylon fabric at the same rate in the temperature range from 60.degree. to 100.degree. C., so that the dyeing always remains brown. The dye is also suitable for combination dyeing to achieve beige hues which are very light-fast and in particular are non-phototropic to light from incandescent lamps (no reversible change to a greener hue).

EXAMPLE 2

19.5 parts of 2,4-dichloroaniline-6-sulfonic acid are diazotized by a procedure similar to that described in Example 1. Excess nitrous acid is then destroyed in a conventional manner, and the diazonium salt mixture is buffered to pH 2-4 with sodium acetate. A solution of 16.7 parts of 1-(2-methoxyethyl)-6-hydroxy-3-cyano-4-methylpyrid-2-one in 200 parts by volume of water, 10 parts of 50% strength sodium hydroxide solution and 0.3 part of a dispersant which is effective under acidic conditions is then run in. The coupling mixture is stirred for a further 60-80 minutes, after which it is acidified to pH 0.3-0.5 with concentrated hydrochloric acid, and the precipitated dye of the formula ##STR18## is filtered off under suction, washed salt-free with a little water and dried to give 36 parts of a yellow powder. 20 parts of this powder are suspended in a mixture of 20 parts of butyldiglycol and 60 parts of 2- or 3-methoxypropanol, and the suspension is neutralized with lithium hydroxide. Clear filtration gives a honey yellow solution. This dye solution is very useful for dyeing leather lemon yellow by a conventional spray-dyeing method. The absorption maximum of the dye in a 9:1 dimethylformamide/glacial acetic acid mixture is determined as 412 nm.

EXAMPLE 3

22.1 parts of 2-trifluoromethyl-4-chloroaniline-6-sulfonic acid are diazotized by a procedure similar to that described in Example 1. 31 parts of the coupling component of the formula ##STR19## in the form of a roughly 50% strength water-moist paste, are then introduced into the diazonium salt mixture, after which the pH of the coupling mixture is brought to 4.5-5 with 25% strength sodium hydroxide solution. When coupling is complete, the mixture is neutralized with further sodium hydroxide solution and is then spray dried.

73 parts of a red powder are obtained. The resulting dye is of the formula ##STR20## and has an absorption maximum of 430 nm in a 9:1 dimethylformamide/glacial acetic acid mixture. It dyes wool and nylon in fast intense golden yellow hues.

EXAMPLE 4

19.5 parts of 2,4-dichloroaniline-6-sulfonic acid are diazotized by a procedure similar to that described in Example 1. When excess nitrous acid has been destroyed, 24.2 parts of 2-phenyl-4,6-bis-(3-hydroxypropylamino)-pyrimidine are added, and stirring is continued until the coupling component has dissolved. Thereafter, a dispersant which is highly effective at pH 7-10 is added and the pH of the coupling mixture is brought to 8.5-9.2 with sodium hydroxide solution and then with a little sodium carbonate solution (as a buffer). Stirring is continued overnight, and the resulting dye of the formula ##STR21## (.lambda.max: 431.5 nm (CH.sub.3).sub.2 NCHO/CH.sub.3 CO.sub.2 H=9:1) is then precipitated by adding about 30 parts of sodium chloride and acidifying the mixture to pH 4-4.5, and is isolated in a conventional manner to give about 50 parts of a reddish brown powder which dissolves in water to give a yellow solution and dyes nylon fabric and wool in very fast golden yellow hues. The dye has great migrating power.

TABLE 1__________________________________________________________________________ ##STR22## .lambda.maxNo. R R.sup.1 R.sup.2 R.sup.3 Hue (nm)__________________________________________________________________________ 1 Cl H C.sub.3 H.sub.6 OCH.sub.3 C.sub.3 H.sub.7 yellow 413 2 Cl H C.sub.3 H.sub.6 OH C.sub.3 H.sub.7 yellow 413 3 Cl H C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH CH.sub.3 yellow 411 4 Cl H C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH H yellow 412 5 Cl H C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH CH.sub.3 yellow 409 6 Cl H C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3 CH.sub.3 yellow 409 7 Cl H C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n) CH.sub.3 yellow 409 8 Cl H C.sub.3 H.sub.6 OCH.sub.3 CH.sub.3 yellow 410 9 Cl H C.sub.3 H.sub.6 OC.sub.2 H.sub.5 CH.sub.3 yellow 41010 Cl C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH H CH.sub.3 yellow 41211 Cl C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.2 H.sub.5 H CH.sub.3 yellow 41112 Cl C.sub.2 H.sub.5 C.sub.2 H.sub.4 OH CH.sub.3 golden yellow 42213 Cl CH.sub.3 C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH CH.sub.3 golden yellow 42014 Cl C.sub.2 H.sub.5 C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH CH.sub.3 golden yellow 42215 Cl C.sub.2 H.sub.5 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH CH.sub.3 golden yellow 42116 Cl CH.sub.2 CHCH.sub.2 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH CH.sub.3 golden yellow 42217 Cl CH(CH.sub.3).sub.2 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH CH.sub.3 golden yellow 42018 Cl CH.sub.2 CH.sub.2 OCH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3 CH.sub. 3 golden yellow 41919 Cl (CH.sub.2).sub.3 OCH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3 CH.sub.3 golden yellow 42120 Cl (CH.sub.2).sub.3 OCH.sub.3 (CH.sub.2).sub.3 OCH.sub.3 CH.sub.3 golden yellow 42721 Cl ##STR23## C.sub.2 H.sub.4 OCH.sub.3 CH.sub.3 golden yellow 42222 Cl CH.sub.2 CH.sub.2 OCH.sub.3 (CH.sub.2).sub.3 OCH.sub.3 CH.sub.3 golden yellow 42323 Cl CH.sub.2 CH.sub.2 OCH.sub.3 CH.sub.2 CH.sub.2 OH CH.sub.3 golden yellow 42324 Cl CH.sub.2 CH.sub.2 OCH.sub.3 ##STR24## CH.sub.3 golden yellow 42325 Cl CH.sub.2 CH.sub.2 OCH.sub.3 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 CH.sub.3 golden yellow 42126 Cl CH.sub.2 CH.sub.2 OCH.sub.3 (CH.sub.2).sub.3 OCH(CH.sub.3).sub.2 CH.sub.3 golden yellow 42327 Cl CH.sub.2 CH.sub.2 OCH.sub.3 (CH.sub.2).sub.3 O(CH.sub.2).sub.4 OH CH.sub.3 golden yellow 42328 Cl CH.sub.2 CH.sub.2 OCH.sub. 3 (CH.sub.2).sub.3 OH CH.sub.3 golden yellow 42429 Cl ##STR25## CH.sub.2 CH.sub.2 OCH.sub.3 CH.sub.3 golden yellow 42330 Cl ##STR26## (CH.sub.2).sub.3 OCH.sub.3 CH.sub.3 orange 42331 Cl ##STR27## (CH.sub.2).sub.2 OH CH.sub.3 golden yellow 42232 Cl ##STR28## (CH.sub.2).sub.3 OH CH.sub.3 orange 42433 Cl ##STR29## (CH.sub.2).sub.3 OC.sub.2 H.sub.5 CH.sub.3 orange 42434 Cl ##STR30## ##STR31## CH.sub.3 orange 42435 Cl (CH.sub.2).sub.3 OH (CH.sub.2).sub.2 OH CH.sub.3 golden yellow 42536 Cl (CH.sub.2).sub.3 OH ##STR32## CH.sub.3 golden yellow 42637 Cl (CH.sub.2).sub.3 OH (CH.sub.2).sub.2 OCH.sub.3 CH.sub.3 golden yellow 42638 Cl (CH.sub.2).sub.3 OH (CH.sub.2).sub.3 OCH.sub.3 CH.sub.3 golden yellow 42739 Cl (CH.sub.2).sub.3 OH (CH.sub.2).sub.3 OC.sub.2 H.sub.5 CH.sub.3 golden yellow 42640 Cl (CH.sub.2).sub.2 OH (CH.sub.2).sub.2 OH CH.sub.3 golden yellow 42041 Cl (CH.sub.2).sub.2 OH (CH.sub.2).sub.3 OH CH.sub.3 golden yellow 42342 Cl (CH.sub.2).sub.2 OH ##STR33## CH.sub.3 golden yellow 42343 Cl (CH.sub.2).sub.2 OH (CH.sub.2).sub.2 OCH.sub.3 CH.sub.3 golden yellow 42144 Cl (CH.sub.2).sub.2 OH (CH.sub.2).sub.3 OCH.sub.3 CH.sub.3 golden yellow 42345 Cl (CH.sub.2).sub.2 OH (CH.sub.2).sub.3 OC.sub.2 H.sub.5 CH.sub.3 golden yellow 42346 Cl (CH.sub.2).sub.2 OH C.sub.4 H.sub.9 (n) CH.sub.3 golden yellow 42747 Cl (CH.sub.2).sub.2 OH (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5 CH.sub.3 golden yellow 42548 Cl (CH.sub.2).sub.2 OH (CH.sub.2).sub.2 C.sub.6 H.sub.5 CH.sub.3 golden yellow 42249 Cl (CH.sub.2).sub.2 OH ##STR34## CH.sub.3 golden yellow 42250 Cl (CH.sub.2).sub.2 OH ##STR35## CH.sub.3 golden yellow 42351 Cl C.sub.2 H.sub.5 ##STR36## CH.sub.3 golden yellow 42252 Cl C.sub.2 H.sub.5 C.sub.2 H.sub.5 CH.sub.3 golden yellow 42053 Cl (CH.sub.2).sub.2 CN (CH.sub.2).sub.3 OH CH.sub.3 golden yellow 42254 Cl (CH.sub.2).sub.5 CN (CH.sub.2).sub.3 OH CH.sub.3 golden yellow 42355 Cl (CH.sub.2).sub.2 C.sub.6 H.sub.5 (CH.sub.2).sub.2 OH CH.sub.3 golden yellow 42156 Cl ##STR37## C.sub.4 H.sub.9 (n) CH.sub.3 golden yellow 42357 Cl CH.sub.2 CHCH.sub.2 (CH.sub.2).sub.2 OH CH.sub.3 golden yellow 42258 Cl CH.sub.2 CHCH.sub.2 (CH.sub.2).sub.3 OH CH.sub.3 golden yellow 42359 Br (CH.sub.2).sub.3 OH (CH.sub.2).sub.3 OH CH.sub.3 golden yellow 42960 CF.sub.3 (CH.sub.2).sub.3 OH (CH.sub.2).sub.3 OH CH.sub.3 golden yellow 43061 CF.sub.3 (CH.sub.2).sub.2 OCH.sub.3 (CH.sub.2).sub.2 OH CH.sub.3 golden yellow 42862 Cl ##STR38## (CH.sub.2).sub.2 OH CH.sub.3 golden yellow 42563 Cl ##STR39## (CH.sub.2).sub.3 OH CH.sub.3 golden yellow 42664 Cl ##STR40## (CH.sub.2).sub.3 OH CH.sub.3 golden yellow 42665 Cl ##STR41## (CH.sub.2).sub.2 OH CH.sub.3 golden yellow 42466 Cl (CH.sub.2 ).sub.2 OCOCH.sub.3 (CH.sub.2).sub.2 OCOCH.sub.3 CH.sub.3 golden yellow 42067 Cl (CH.sub.2).sub.3 OCHO (CH.sub.2).sub.3 OCHO CH.sub.3 golden yellow 42168 Cl (CH.sub.2).sub.2 OCH.sub.3 (CH.sub.2).sub.3 OCHO CH.sub.3 golden yellow 42169 Cl (CH.sub.2).sub.3 OCHO (CH.sub.2).sub.2 OCH.sub.3 CH.sub.3 golden yellow 42170 Cl (CH.sub.2).sub.4 OH (CH.sub.2).sub.4 OH CH.sub.3 golden yellow 43071 Cl (CH.sub.2).sub.4 OH (CH.sub.2).sub.3 OH CH.sub.3 golden yellow 42972 Cl (CH.sub.2).sub.4 OH (CH.sub.2).sub.2 OH CH.sub.3 golden yellow 42973 Cl (CH.sub.2).sub.4 OH (CH.sub.2).sub.2 OCH.sub.3 CH.sub.3 golden yellow 428__________________________________________________________________________ TABLE 2__________________________________________________________________________ ##STR42##No. R.sup.1 R.sup.2 R.sup.3 Hue__________________________________________________________________________ ##STR43## C.sub.2 H.sub.5 H golden yellow2 ##STR44## C.sub.2 H.sub.5 C.sub.2 H.sub.5 orange3 ##STR45## C.sub.4 H.sub.9 (n) H golden yellow4 ##STR46## C.sub.3 H.sub.6 OCH.sub.3 H golden yellow5 ##STR47## C.sub.2 H.sub.4 OCH.sub.3 H golden yellow6 ##STR48## C.sub.3 H.sub.6 OC.sub.2 H.sub.5 H golden yellow7 ##STR49## C.sub.3 H.sub.6 OH H golden yellow8 ##STR50## C.sub.4 H.sub.8 OH H golden yellow9 ##STR51## C.sub.4 H.sub.9 (n) C.sub.4 H.sub.9 (n) orange10 ##STR52## ##STR53## H golden yellow11 ##STR54## C.sub.2 H.sub.4 OH H golden yellow12 ##STR55## C.sub.3 H.sub.6 OH H golden yellow13 ##STR56## C.sub.4 H.sub.9 (n) H golden yellow14 ##STR57## C.sub.3 H.sub.6 OCH.sub.3 H golden yellow15 ##STR58## C.sub.2 H.sub.4 OCH.sub.3 H golden yellow16 ##STR59## ##STR60## H golden yellow17 C.sub.4 H.sub.8 OH ##STR61## H golden yellow18 C.sub.3 H.sub.6 OH ##STR62## orange19 C.sub.2 H.sub.4 OCH.sub.3 ##STR63## orange20 C.sub.3 H.sub.6 OCH.sub.3 ##STR64## orange21 C.sub.3 H.sub.6 OH ##STR65## orange__________________________________________________________________________ TABLE 3__________________________________________________________________________ ##STR66## .lambda.maxNo. R R.sup.1 R.sup.2 R.sup.3 Hue (nm)__________________________________________________________________________1 Cl C.sub.3 H.sub.6 OH C.sub.6 H.sub.5 C.sub.2 H.sub.4 OH golden yellow 4292 Cl C.sub.3 H.sub.6 OH C.sub.6 H.sub.5 C.sub.2 H.sub.4 OCH.sub.3 golden yellow 4283 Cl C.sub.3 H.sub.6 OH C.sub.6 H.sub.5 C.sub.3 H.sub.6 OCH.sub.3 golden yellow 4304 Cl C.sub.3 H.sub.6 OH C.sub.6 H.sub.5 C.sub.2 H.sub.4 OC.sub.2 H.sub.5 golden yellow 4285 Cl C.sub.3 H.sub.6 OH C.sub.6 H.sub.5 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH yellow 4276 Cl C.sub.3 H.sub.6 OH C.sub.6 H.sub.5 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3 yellow 4277 Cl C.sub.3 H.sub.6 OH C.sub.6 H.sub.5 C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OH golden yellow 4308 Cl C.sub.3 H.sub.6 OH C.sub.6 H.sub.5 C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH golden yellow 4309 Cl C.sub.2 H.sub.4 OH C.sub.6 H.sub.5 C.sub.2 H.sub.4 OCH.sub.3 yellow 42610 Cl C.sub.2 H.sub.4 OH C.sub.6 H.sub.5 C.sub.3 H.sub.6 OCH.sub.3 yellow 42711 Cl C.sub.2 H.sub.4 OH C.sub.6 H.sub.5 C.sub.3 H.sub.6 OC.sub.3 H.sub.7 yellow 42812 Cl C.sub.2 H.sub.4 OCH.sub.3 C.sub.6 H.sub.5 C.sub.2 H.sub.4 OCH.sub.3 yellow 42613 Cl C.sub.2 H.sub.4 OCH.sub.3 C.sub.6 H.sub.5 C.sub.3 H.sub.6 OCH.sub.3 yellow 42814 Cl C.sub.3 H.sub.6 OCH.sub.3 C.sub.6 H.sub.5 C.sub.3 H.sub.6 OCH.sub.3 golden yellow 42915 Cl ##STR67## C.sub.6 H.sub.5 C.sub.3 H.sub.6 OCH.sub.3 golden yellow 43016 Cl ##STR68## C.sub.6 H.sub.5 ##STR69## golden yellow 43117 Br ##STR70## C.sub.6 H.sub.5 ##STR71## golden yellow 43118 Br C.sub.3 H.sub.6 OH C.sub.3 H.sub.6 C.sub.3 H.sub.6 OH golden yellow 43219 Cl C.sub.3 H.sub.6 OH ##STR72## C.sub.3 H.sub.6 OH golden yellow 43220 Cl C.sub.3 H.sub.6 OH ##STR73## C.sub.3 H.sub.6 OH golden yellow 43221 Cl C.sub.4 H.sub.8 OH C.sub.6 H.sub.5 C.sub.4 H.sub.8 OH golden yellow 43322 Cl C.sub.2 H.sub.4 OH ##STR74## C.sub.2 H.sub.4 OH golden yellow 43123 Cl ##STR75## ##STR76## C.sub.2 H.sub.4 OH yellow 42824 CF.sub.3 C.sub.3 H.sub.6 OH C.sub.6 H.sub.6 C.sub.3 H.sub.6 OH golden yellow 43425 CF.sub.3 C.sub.3 H.sub.6 OH C.sub.6 H.sub.5 C.sub.2 H.sub.4 OH golden yellow 43326 CF.sub.3 ##STR77## C.sub.6 H.sub.5 C.sub.2 H.sub.4 OH golden yellow 43327 CF.sub.3 ##STR78## C.sub.6 H.sub.5 ##STR79## golden yellow 43528 CF.sub.3 C.sub.2 H.sub.4 OCH.sub.3 C.sub.6 H.sub.5 ##STR80## golden yellow 43229 CF.sub.3 C.sub.2 H.sub.4 OCH.sub.3 C.sub.6 H.sub.5 C.sub.2 H.sub.4 OH golden yellow 43230 CF.sub.3 C.sub.2 H.sub.4 OCH.sub.3 C.sub.6 H.sub.5 C.sub.3 H.sub.6 OH golden yellow 43231 CF.sub.3 C.sub. 3 H.sub.6 OCH.sub.3 C.sub.6 H.sub.5 C.sub.3 H.sub.6 OH golden yellow 43532 CF.sub.3 ##STR81## ##STR82## C.sub.2 H.sub.4 OH golden yellow 43333 Cl ##STR83## C.sub.6 H.sub.5 ##STR84## golden yellow 43434 CH.sub.3 C.sub.2 H.sub.4 OH C.sub.6 H.sub.5 C.sub.2 H.sub.4 OH golden yellow 432__________________________________________________________________________ TABLE 4______________________________________ ##STR85## .lambda.maxNo. R R.sup.1 R.sup.2 R.sup.3 Hue (nm)______________________________________ 1Cl Cl C.sub.2 H.sub.4 OH H green- 412 ish yellow 2Cl Cl C.sub.2 H.sub.4 OH CH.sub.3 green- 412 ish yellow 3Cl Cl C.sub.2 H.sub.4 OH C.sub.2 H.sub.5 green- 411 ish yellow 4Cl Cl C.sub.2 H.sub.4 OH C.sub.3 H.sub.7 green- 410 (n) ish yellow 5Cl Cl C.sub.3 H.sub.6 OH CH.sub.3 green- 412 ish yellow 6Cl Cl C.sub.3 H.sub.6 OH CH.sub.3 green- 412 ish yellow 7Cl Cl C.sub.3 H.sub.6 OH C.sub.3 H.sub.7 green- 411 (n) ish yellow 8Cl Cl C.sub.3 H.sub.6 OCOCH.sub.3 CH.sub.3 green- 413 ish yellow 9Cl Cl C.sub.3 H.sub.6 OCH.sub.3 C.sub.3 H.sub.7 green- 412 (n) ish yellow10Cl Cl C.sub.3 H.sub.6 OCH.sub.3 CH.sub.3 green- 412 ish yellow11Br Cl C.sub.3 H.sub.6 OCH.sub.3 CH.sub.3 green- 413 ish yellow12Cl Cl C.sub.3 H.sub.6 OCH.sub.3 H green- 412 ish yellow13Cl Cl C.sub.6 H.sub.13 (n) CH.sub.3 green- 413 ish yellow14Cl Cl C.sub.3 H.sub.6 OC.sub.2 H.sub.5 CH.sub.3 green- 413 ish yellow15Cl Cl C.sub.3 H.sub.6 OC.sub.3 H.sub.7 CH.sub.3 green- 412 ish yellow16Cl Cl C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH CH.sub.3 green- 412 ish yellow17Cl CF.sub.3 C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH CH.sub.3 green- 407 ish yellow18Cl CF.sub.3 C.sub.6 H.sub.12 OH CH.sub.3 green- 408 ish yellow19Cl Cl C.sub.6 H.sub.12 OH CH.sub.3 green- 413 ish yellow20Cl CF.sub.3 C.sub.3 H.sub.6 OCH.sub.3 CH.sub.3 green- 407 ish yellow21Cl CF.sub.3 CH.sub.2 CH.sub.2C.sub.6 H.sub.5 CH.sub.3 green- 407 ish yellow22Cl CF.sub.3 CH.sub.2 CHCH.sub.2 CH.sub.3 green- 407 ish yellow23Cl CF.sub.3 C.sub.6 H.sub.13 (n) CH.sub.3 green- 408 ish yellow24Cl CF.sub.3 ##STR86## CH.sub.3 green- ish yellow 40725Cl Cl ##STR87## CH.sub.3 green- ish yellow 41226Cl Cl ##STR88## CH.sub.3 green- ish yellow 41327Cl Cl C.sub.4 H.sub.8 OH CH.sub.3 green- 413 ish yellow28Cl Cl C.sub.6 H.sub.12 OH CH.sub.3 green- 413 ish yellow29H SO.sub.2 C.sub.6 H.sub.5 C.sub.4 H.sub.8 OH CH.sub.3 green- ish yellow30H SO.sub.2 C.sub.6 H.sub.5 C.sub.3 H.sub.6 OH CH.sub.3 green- ish yellow31Cl CH.sub.3 C.sub.3 H.sub.6 OH CH.sub.3 green- 411 ish yellow32Cl CH.sub.3 C.sub.2 H.sub.4 OH CH.sub.3 green- 412 ish yellow33Cl CH.sub.3 C.sub.3 H.sub.6 OCH.sub.3 CH.sub.3 green- 411 ish yellow34Cl Br C.sub.3 H.sub.6 OCH.sub.3 CH.sub.3 green- 413 ish yellow35Cl Br C.sub.3 H.sub.6 OH CH.sub.3 green- 413 ish yellow36Cl Br C.sub.4 H.sub.8 OH CH.sub.3 green- 413 ish yellow37CH.sub.3 Br C.sub.4 H.sub.8 OH CH.sub.3 green- 414 ish yellow38CH.sub.3 Br C.sub.3 H.sub.6 OH CH.sub.3 green- 414 ish yellow39CH.sub.3 Br C.sub.3 H.sub.6 OCH.sub. 3 CH.sub.3 green- 414 ish yellow40CH.sub.3 Br C.sub.2 H.sub.4 OCH.sub.3 CH.sub.3 green- 414 ish yellow______________________________________ TABLE 5______________________________________ ##STR89## .lambda.maxNo. R A Hue (nm)______________________________________1 Cl C.sub.2 H.sub.4 greenish 413 yellow2 Cl C.sub.3 H.sub.6 greenish 413 yellow3 Cl ##STR90## greenish yellow 4134 Cl (CH.sub.2).sub.6 greenish 412 yellow5 Cl (CH.sub.2).sub.3 O(CH.sub.2).sub.3 greenish 413 yellow6 Br (CH.sub.2).sub.3 O(CH.sub.2).sub.2 O(CH.sub.2).sub.3 greenish 413 yellow7 Br C.sub.3 H.sub.6 greenish 413 yellow8 CF.sub.3 C.sub.2 H.sub.4 greenish 417 yellow9 CF.sub.3 C.sub.3 H.sub.6 greenish 408 yellow10 CF.sub.3 ##STR91## greenish yellow 40811 CF.sub.3 (CH.sub.2).sub.6 greenish 408 yellow12 CF.sub.3 (CH.sub.2).sub.3 O(CH.sub.2).sub.3 greenish 408 yellow13 Cl (CH.sub.2).sub.3 O(CH.sub.2).sub.2 O(CH.sub.2).sub.3 greenish 412 yellow14 Cl (CH.sub.2).sub.3 O(CH.sub.2).sub.4 O(CH.sub.2).sub.3 greenish 413 yellow15 Cl CH.sub.2(CH.sub.3).sub.2CH.sub.2 greenish 413 yellow______________________________________ TABLE 6______________________________________ ##STR92##No. A R.sup.1 R.sup.2 Hue______________________________________ 1 CH.sub.2 CH.sub.2 Cl C.sub.2 H.sub.4 OH golden yellow 2 (CH.sub.2).sub.3 Cl C.sub.2 H.sub.4 OH golden yellow 3 (CH.sub.2).sub.3 Cl C.sub.3 H.sub.6 OH golden yellow 4 (CH.sub.2).sub.3 Cl C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH golden yellow 5 (CH.sub.2).sub.3 Cl C.sub.2 H.sub.4 OCH.sub.3 golden yellow 6 (CH.sub.2).sub.3 Cl C.sub.3 H.sub.6 OCH.sub.3 golden yellow 7 (CH.sub.2).sub.4 Cl C.sub.2 H.sub.4 OH golden yellow 8 (CH.sub.2).sub.4 Cl C.sub.3 H.sub.6 OH golden yellow 9 (CH.sub.2).sub.3 O(CH.sub.2).sub.2 O(CH.sub.2).sub.3 Cl C.sub.2 H.sub.4 OH golden yellow10 (CH.sub.2).sub.3 O(CH.sub.2).sub.2 O(CH.sub.2).sub.3 Cl C.sub.3 H.sub.6 OH golden yellow11 (CH.sub.2).sub.3 O(CH.sub.2).sub.4 O(CH.sub.2).sub.3 Cl C.sub.3 H.sub.6 OH golden yellow12 (CH.sub.2).sub.3 O(CH.sub.2).sub.4 O(CH.sub.2).sub.3 Cl C.sub.2 H.sub.4 OCH.sub.3 golden yellow13 (CH.sub.2).sub. 3 O(CH.sub.2).sub.4 O(CH.sub.2).sub.3 Cl C.sub.3 H.sub.6 OCH.sub.3 golden yellow14 (CH.sub.2).sub.3 O(CH.sub.2).sub.4 O(CH.sub.2).sub.3 CF.sub.3 C.sub.3 H.sub.6 OCH.sub.3 golden yellow15 (CH.sub.2).sub.3 CF.sub.3 C.sub.3 H.sub.6 OCH.sub.3 golden yellow16 (CH.sub.2).sub.6 Cl C.sub.2 H.sub.4 OCH.sub.3 golden yellow17 ##STR93## Cl C.sub.2 H.sub.4 OH golden yellow18 ##STR94## Cl C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH golden yellow19 (CH.sub.2).sub.3 Cl C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH golden yellow20 (CH.sub.2).sub.3 Cl C.sub.4 H.sub.8 OH golden yellow21 (CH.sub.2).sub.3 CH.sub.3 C.sub.2 H.sub. 4 OH golden yellow______________________________________ TABLE 7__________________________________________________________________________ ##STR95## .lambda.maxNo. R R.sup.1 R.sup.2 K Hue (nm)__________________________________________________________________________ 1 H CH.sub.3 Cl H H Cl SO.sub.2 C.sub.6 H.sub.5 SO.sub.2 C.sub.6 H.sub.5 Cl ##STR96## orange orange orange 4 H CH.sub.3 Cl Cl SO.sub.2 C.sub.6 H.sub.5 SO.sub.2 C.sub.6 H.sub.5 ##STR97## orange orange 6 Cl Cl Cl H Cl SO.sub.2 C.sub.6 H.sub.5 ##STR98## orange orange 8 H H H H H H COCH.sub.3 CF.sub.3 COC.sub.6 H.sub.5 ##STR99## orange orange orange11 12 13 H H F H H H COC.sub.6 H.sub.5 COCH.sub.3 Br ##STR100## orange orange orange14 15 Br Cl H H F F ##STR101## orange orange16 17 18 19 H Cl SO.sub.2 C.sub.4 H.sub.9 Cl Cl H H Cl Cl SO.sub.2 C.sub.4 H.sub.9 Cl Cl ##STR102## orange orange orange orange 42520 21 Cl Cl Cl H Cl CH.sub.3 ##STR103## orange orange 425__________________________________________________________________________ TABLE 8______________________________________ ##STR104## .lambda.maxNo. R.sup.1 R.sup.2 (nm)______________________________________ ##STR105## C.sub.6 H.sub.5 4322 ##STR106## ##STR107## 4333 ##STR108## ##STR109## 4324 ##STR110## ##STR111## 4355 ##STR112## ##STR113## 4356 ##STR114## ##STR115## 4347 ##STR116## C.sub.6 H.sub.5 4308 ##STR117## ##STR118## 4329 ##STR119## ##STR120## 43010 ##STR121## ##STR122## 43011 ##STR123## C.sub.6 H.sub.5 43012 ##STR124## ##STR125## 43513 ##STR126## ##STR127## 431______________________________________

EXAMPLE 5

19.5 parts of 2,4-dichloroaniline-5-sulfonic acid are stirred overnight with 50 parts of 15% strength hydrochloric acid in the presence of a wetting agent which is effective under acidic conditions. Thereafter, the mixture is cooled with ice to 0.degree. C., 27 parts by volume of a 23% strength sodium nitrite solution are added in the course of from 5 to 20 minutes, and the suspension is stirred for a further 3 hours at from 0.degree. to 5.degree. C. A solution or suspension of 21.2 parts of 2,6-bis-(3-hydroxypropylamino)-3-cyano-4-methylpyridine in 120 parts by volume of water and 7 parts by volume of concentrated hydrochloric acid is then run in. Stirring is continued for from 15 to 30 minutes, and the pH of the mixture is then slowly increased to 1-1.5 by adding sodium hydroxide solution or sodium formate. The acid formed as a result of the coupling reaction is then bound continuously by adding appropriate amounts of sodium hydroxide solution or sodium formate. When the mixture has been kept at pH 1-1.5 for about 30-60 minutes, the pH is increased to 3-3.5 by adding dilute sodium hydroxide solution or sodium acetate. The coupling reaction quickly comes to an end. The resulting dye of the formula ##STR128## is precipitated virtually quantitatively by adding 40 parts of sodium chloride and is then isolated by filtration. After drying, 44 parts of a brown powder are obtained.

The dye dissolves in water to give a yellow solution and dyes nylon and wool in intense, lightfast, golden yellow hues.

The absorption maximum of a solution of about 0.020 part of the dye in 900 parts by volume of dimethylformamide and 150 parts by volume of glacial acetic acid is 457 nm (water: 435 nm).

TABLE 9______________________________________ ##STR129##No. R.sup.1 R.sup.2 .lambda.max (nm)______________________________________ ##STR130## C.sub.6 H.sub.5 4592 ##STR131## ##STR132## 4593 ##STR133## ##STR134## 4594 ##STR135## ##STR136## 4605 ##STR137## ##STR138## 4606 ##STR139## ##STR140## 4607 ##STR141## C.sub.6 H.sub.5 4568 ##STR142## ##STR143## 4599 ##STR144## ##STR145## 45710 ##STR146## ##STR147## 45711 ##STR148## C.sub.6 H.sub.5 45812 ##STR149## ##STR150## 46013 ##STR151## ##STR152## 458______________________________________ TABLE 10__________________________________________________________________________ ##STR153##No. R R.sup.1 R.sup.2 R.sup.3 Hue .lambda.max (nm)__________________________________________________________________________ 1 Cl H C.sub.3 H.sub.6 OCH.sub.3 C.sub.3 H.sub.7 yellow 446 2 Cl H C.sub.3 H.sub.6 OH C.sub.3 H.sub.7 yellow 446 3 Cl H C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH CH.sub.3 yellow 441 4 Cl H C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH H yellow 443 5 Cl H C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH CH.sub.3 yellow 443 6 Cl H C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3 CH.sub.3 yellow 444 7 Cl H C.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n) CH.sub.3 yellow 446 8 Cl H C.sub.3 H.sub.6 OCH.sub.3 CH.sub.3 yellow 446 9 Cl H C.sub.3 H.sub.6 OC.sub.2 H.sub.5 CH.sub.3 yellow 44610 Cl C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH H CH.sub.3 yellow 44811 Cl C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OC.sub.2 H.sub.5 H CH.sub.3 yellow 44912 Cl C.sub.2 H.sub.5 C.sub.2 H.sub.4 OH CH.sub.3 golden yellow 45513 Cl CH.sub.3 C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH CH.sub.3 golden yellow 45414 Cl C.sub.2 H.sub.5 C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH CH.sub.3 golden yellow 45515 Cl C.sub.2 H.sub.5 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH CH.sub.3 golden yellow 45316 Cl CH.sub.2 CHCH.sub.2 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH CH.sub.3 golden yellow 45417 Cl CH(CH.sub.3).sub.2 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH CH.sub.3 golden yellow 45318 Cl CH.sub.2 CH.sub.2 OCH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3 CH.sub.3 golden yellow 45419 Cl (CH.sub.2).sub.3 OCH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3 CH.sub.3 golden yellow 45520 Cl (CH.sub.2).sub.3 OCH.sub.3 (CH.sub.2).sub.3 OCH.sub.3 CH.sub.3 golden yellow 45621 Cl ##STR154## C.sub.2 H.sub.4 OCH.sub.3 CH.sub.3 golden yellow 45522 Cl CH.sub.2 CH.sub.2 OCH.sub.3 (CH.sub.2).sub.3 OCH.sub.3 CH.sub.3 golden yellow 45523 Cl CH.sub.2 CH.sub.2 OCH.sub.3 CH.sub.2 CH.sub.2 OH CH.sub.3 golden yellow 45324 Cl CH.sub.2 CH.sub.2 OCH.sub.3 ##STR155## CH.sub.3 golden yellow 45325 Cl CH.sub.2 CH.sub.2 OCH.sub.3 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 CH.sub.3 golden yellow 45226 Cl CH.sub.2 CH.sub.2 OCH.sub.3 (CH.sub.2).sub.3 OCH(CH.sub.3).sub.2 CH.sub.3 golden yellow 45427 Cl CH.sub.2 CH.sub.2 OCH.sub.3 (CH.sub.2).sub.3 O(CH.sub.2).sub.4 OH CH.sub.3 golden yellow 45428 Cl CH.sub.2 CH.sub.2 OCH.sub.3 (CH.sub.2).sub.3 OH CH.sub.3 golden yellow 45429 Cl ##STR156## CH.sub.2 CH.sub.2 OCH.sub.3 CH.sub.3 golden yellow 45230 Cl ##STR157## (CH.sub.2).sub.3 OCH.sub.3 CH.sub.3 orange 45331 Cl ##STR158## (CH.sub.2).sub.2 OH CH.sub.3 golden yellow 45232 Cl ##STR159## (CH.sub.2).sub.3 OH CH.sub.3 orange 45333 Cl ##STR160## (CH.sub.2).sub.3 OC.sub.2 H.sub.5 CH.sub.3 orange 45334 Cl ##STR161## ##STR162## CH.sub.3 orange 45335 Cl (CH.sub.2).sub.3 OH (CH.sub.2).sub.2 OH CH.sub.3 golden yellow 45236 Cl (CH.sub.2).sub.3 OH ##STR163## CH.sub.3 golden yellow 45537 Cl (CH.sub.2).sub.3 OH (CH.sub.2).sub.2 OCH.sub.3 CH.sub.3 golden yellow 45338 Cl (CH.sub. 2).sub.3 OH (CH.sub.2).sub.3 OCH.sub.3 CH.sub.3 golden yellow 45639 Cl (CH.sub.2).sub.3 OH (CH.sub.2).sub.3 OC.sub.2 H.sub.5 CH.sub.3 golden yellow 45640 Cl (CH.sub.2).sub.2 OH (CH.sub.2).sub.2 OH CH.sub.3 golden yellow 45241 Cl (CH.sub.2).sub.2 OH (CH.sub.2).sub.3 OH CH.sub.3 golden yellow 45342 Cl (CH.sub.2).sub.2 OH ##STR164## CH.sub.3 golden yellow 45343 Cl (CH.sub.2).sub.2 OH (CH.sub.2).sub.2 OCH.sub.3 CH.sub.3 golden yellow 45144 Cl (CH.sub.2).sub.2 OH (CH.sub.2).sub.2 OCH.sub.3 CH.sub.3 golden yellow 45345 Cl (CH.sub.2).sub.2 OH (CH.sub.2).sub.3 OC.sub.2 H.sub.5 CH.sub.3 golden yellow 45346 Cl (CH.sub.2).sub.2 OH C.sub.4 H.sub.9 (n) CH.sub.3 golden yellow 45647 Cl (CH.sub.2).sub.2 OH (CH.sub.2).sub.3 OCH.sub.2 C.sub.6 H.sub.5 CH.sub.3 golden yellow 45548 Cl (CH.sub.2).sub.2 OH (CH.sub.2).sub.2 C.sub.6 H.sub. 5 Ch.sub.3 golden yellow 45049 Cl (CH.sub.2).sub.2 OH ##STR165## CH.sub.3 golden yellow 45550 Cl (CH.sub.2).sub.2 OH ##STR166## CH.sub.3 golden yellow 45451 Cl C.sub.2 H.sub.5 ##STR167## CH.sub.3 golden yellow 45152 Cl C.sub.2 H.sub.5 C.sub.2 H.sub.5 CH.sub.3 golden yellow 44953 Cl (CH.sub.2).sub.2 CN (CH.sub.2).sub.3 OH CH.sub.3 golden yellow 45054 Cl (CH.sub.2).sub.5 CN (CH.sub.2).sub.3 OH CH.sub.3 golden yellow 45755 Cl (CH.sub.2).sub.2 C.sub.6 H.sub.5 (CH.sub.2).sub.2 OH CH.sub.3 golden yellow 44856 Cl ##STR168## C.sub.4 H.sub.9 (n) CH.sub.3 golden yellow 45057 Cl CH.sub.2 CHCH.sub. 2 (CH.sub.2).sub.2 OH CH.sub.3 golden yellow 45258 Cl CH.sub.2 CHCH.sub.2 (CH.sub.2).sub.3 OH CH.sub.3 golden yellow 45459 Br (CH.sub.2).sub.3 OH (CH.sub.2).sub.3 OH CH.sub.3 golden yellow 45760 CF.sub.3 (CH.sub.2).sub.3 OH (CH.sub.2).sub.3 OH CH.sub.3 golden yellow 45861 CF.sub.3 (CH.sub.2).sub.2 OCH.sub.3 (CH.sub.2).sub.2 OH CH.sub.3 golden yellow 45662 Cl ##STR169## (CH.sub.2).sub.2 OH CH.sub.3 golden yellow 45363 Cl ##STR170## (CH.sub.2).sub.3 OH CH.sub.3 golden yellow 45464 Cl ##STR171## (CH.sub.2).sub.3 OH CH.sub.3 golden yellow 45565 Cl ##STR172## (CH.sub.2).sub.2 OH CH.sub.3 golden yellow 45466 Cl (CH.sub.2).sub.2 OCOCH.sub.3 (CH.sub.2).sub.2 OCOCH.sub.3 CH.sub.3 golden yellow 45067 Cl (CH.sub.2).sub.3 OCHO (CH.sub.2).sub.3 OCHO CH.sub.3 golden yellow 45468 Cl (CH.sub.2).sub.2 OCH.sub.3 (CH.sub.2).sub.3 OCHO CH.sub.3 golden yellow 45369 Cl (CH.sub.2).sub.3 OCHO (CH.sub.2).sub.2 OCH.sub.3 CH.sub.3 golden yellow 45370 Cl (CH.sub.2).sub.4 OH (CH.sub.2).sub.4 OH CH.sub.3 golden yellow 45771 Cl (CH.sub.2).sub.4 OH (CH.sub.2).sub.3 OH CH.sub.3 golden yellow 45772 Cl (CH.sub.2).sub.4 OH (CH.sub.2).sub.2 OH CH.sub.3 golden yellow 45673 Cl (CH.sub.2).sub.4 OH (CH.sub.2).sub.2 OCH.sub.3 CH.sub.3 golden yellow 45674 Cl C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3 ##STR173## CH.sub.3 orange 45975 Cl C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3 C.sub.6 H.sub.5 CH.sub.3 orange 45876 Cl C.sub.3 H.sub.5 (OC.sub.2 H.sub.4).sub.2 OCH.sub.3 C.sub.6 H.sub.5 CH.sub.3 orange 45877 Cl C.sub.3 H.sub.6 (OC.sub.2 H.sub.4).sub.2 OCH.sub.3 ##STR174## CH.sub.3 orange 46078 Cl C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH ##STR175## CH.sub.3 orange 45879 Cl C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH C.sub.6 H.sub.5 CH.sub.3 orange 45780 Cl C.sub.6 H.sub.5 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH CH.sub.3 orange 45681 Cl ##STR176## C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH CH.sub.3 orange 45882 Cl ##STR177## C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH CH.sub.3 orange 45883 Cl ##STR178## C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH CH.sub.3 orange 458__________________________________________________________________________ TABLE 11__________________________________________________________________________ ##STR179## .lambda.maxNo. R R.sup.1 R.sup.2 R.sup.3 Hue (nm)__________________________________________________________________________ 1 Cl C.sub.3 H.sub.6 OH C.sub.6 H.sub.5 C.sub.2 H.sub.4 OH golden yellow 435 2 Cl C.sub.3 H.sub.6 OH C.sub.6 H.sub.5 C.sub.2 H.sub.4 OCH.sub.3 golden yellow 433 3 Cl C.sub.3 H.sub.6 OH C.sub.6 H.sub.5 C.sub.3 H.sub.6 OCH.sub.3 golden yellow 436 4 Cl C.sub.3 H.sub.6 OH C.sub.6 H.sub.5 C.sub.2 H.sub.4 OC.sub.2 H.sub.5 golden yellow 434 5 Cl C.sub.3 H.sub.6 OH C.sub.6 H.sub.5 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH yellow 433 6 Cl C.sub.3 H.sub.6 OH C.sub.6 H.sub.5 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3 yellow 433 7 Cl C.sub.3 H.sub.6 OH C.sub.6 H.sub.5 C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OH golden yellow 435 8 Cl C.sub.3 H.sub.6 OH C.sub.6 H.sub.5 C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH golden yellow 436 9 Cl C.sub.2 H.sub.4 OH C.sub.6 H.sub.5 C.sub.2 H.sub.4 OCH.sub.3 yellow 43110 Cl C.sub.2 H.sub.4 OH C.sub.6 H.sub.5 C.sub.3 H.sub.6 OCH.sub.3 yellow 43211 Cl C.sub.2 H.sub.4 OH C.sub.6 H.sub.5 C.sub.3 H.sub.6 OC.sub.3 H.sub.7 yellow 43312 Cl C.sub.2 H.sub.4 OCH.sub.3 C.sub.6 H.sub.5 C.sub.2 H.sub.4 OCH.sub.3 yellow 43113 Cl C.sub.2 H.sub.4 OCH.sub.3 C.sub.6 H.sub.5 C.sub.3 H.sub.6 OCH.sub.3 yellow 43314 Cl C.sub.3 H.sub.6 OCH.sub.3 C.sub.6 H.sub.5 C.sub.3 H.sub.6 OCH.sub.3 golden yellow 43415 Cl ##STR180## C.sub.6 H.sub.5 C.sub.3 H.sub.4 OCH.sub.3 golden yellow 43516 Cl ##STR181## C.sub.6 H.sub.5 ##STR182## golden yellow 43617 Br ##STR183## C.sub.6 H.sub.5 ##STR184## golden yellow 43618 Br C.sub.3 H.sub.6 OH C.sub.6 H.sub.6 C.sub.3 H.sub.6 OH golden yellow 43719 Cl C.sub.3 H.sub.6 OH ##STR185## C.sub.3 H.sub.6 OH golden yellow 43620 Cl C.sub.3 H.sub.6 OH ##STR186## C.sub.3 H.sub.6 OH golden yellow 43721 Cl C.sub.4 H.sub.8 OH C.sub.6 H.sub.5 C.sub.4 H.sub.8 OH golden yellow 43822 Cl C.sub.2 H.sub.4 OH ##STR187## C.sub.2 H.sub.4 OH golden yellow 43623 Cl ##STR188## ##STR189## C.sub.2 H.sub.4 OH yellow 43424 CF.sub.3 C.sub.3 H.sub.6 OH C.sub.6 H.sub.5 C.sub.3 H.sub.6 OH golden yellow 43925 CF.sub.3 C.sub.3 H.sub.6 OH C.sub.6 H.sub.5 C.sub.2 H.sub.4 OH golden yellow 43926 CF.sub.3 ##STR190## C.sub.6 H.sub.5 C.sub.2 H.sub.4 OH golden yellow 439__________________________________________________________________________ TABLE 12__________________________________________________________________________ ##STR191##No. A R.sup.1 R.sup.2 Hue .lambda.max (nm)__________________________________________________________________________1 CH.sub.2 CH.sub.2 Cl C.sub.2 H.sub.4 OH golden yellow 4512 (CH.sub.2).sub.3 Cl C.sub.2 H.sub.4 OH golden yellow 4533 (CH.sub.2).sub.3 Br C.sub.3 H.sub.6 OH golden yellow 4554 (CH.sub.2).sub.3 Cl C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH golden yellow 4555 (CH.sub.2).sub.3 Cl C.sub.2 H.sub.4 OCH.sub.3 golden yellow 4556 (CH.sub.2).sub.3 Cl C.sub.3 H.sub.6 OCH.sub.3 golden yellow 4567 (CH.sub.2).sub.4 Cl C.sub.2 H.sub.4 OH golden yellow 4538 (CH.sub.2).sub.4 Cl C.sub.3 H.sub.6 OH golden yellow 4569 (CH.sub.2).sub.3 O(CH.sub.2).sub.2 O(CH.sub.2).sub.3 Cl C.sub.2 H.sub.4 OH golden yellow 45210 (CH.sub.2).sub.3 O(CH.sub.2).sub.2 O(CH.sub.2).sub.3 Cl C.sub.3 H.sub.6 OH golden yellow 45311 (CH.sub.2).sub.3 O(CH.sub.2).sub.4 O(CH.sub.2).sub.3 Cl C.sub.3 H.sub.6 OH golden yellow 45312 (CH.sub.2).sub.3 O(CH.sub.2).sub.4 O(CH.sub.2).sub.3 Cl C.sub.2 H.sub.4 OCH.sub.3 golden yellow 45213 (CH.sub.2).sub.3 O(CH.sub.2).sub.4 O(CH.sub.2).sub.3 Br C.sub.3 H.sub.6 OCH.sub.3 golden yellow 454__________________________________________________________________________ TABLE 13__________________________________________________________________________ ##STR192## .lambda.maxNo. R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 Hue (nm)__________________________________________________________________________ 1 N(CH.sub.3).sub.2 H H CH.sub.2 CH.sub.2 OH CH.sub.2 CH.sub.2 OH orange 2 N(CH.sub.3).sub.2 H Cl CH.sub.2 CH.sub.2 OH CH.sub.2 CH.sub.2 OH orange 430 3 N(CH.sub.3).sub.2 Cl Cl CH.sub.2 CH.sub.2 OH CH.sub.2 CH.sub.2 OH orange 463 4 N(C.sub.2 H.sub.5).sub.2 Cl Cl CH.sub.2 CH.sub.2 OH CH.sub.2 CH.sub.2 OH orange 463 5 N(C.sub.2 H.sub.5).sub.2 H Cl CH.sub.2 CH.sub.2 OH CH.sub.2 CH.sub.2 OH orange 461 6 N(C.sub.2 H.sub.5).sub.2 H Cl C.sub.3 H.sub.6 OH C.sub.3 H.sub.6 OH orange 432 7 N(CH.sub.3).sub.2 Cl Cl C.sub.2 H.sub.4 OCH.sub.3 C.sub.3 H.sub.6 OH orange 463 8 N(CH.sub.3).sub.2 Cl Cl C.sub.2 H.sub.4 OCH.sub.3 C.sub.2 H.sub.4 OCH.sub.3 orange 462 9 N(CH.sub.3).sub.2 Cl Cl C.sub.3 H.sub.6 OCH.sub.3 C.sub.3 H.sub.6 OCH.sub.3 orange 46510 N(CH.sub.3).sub.2 Cl Cl ##STR193## C.sub.3 H.sub.6 OCH.sub.3 orange 46211 N(CH.sub.3).sub.2 Cl Cl ##STR194## C.sub.2 H.sub.4 OH orange 46112 N(CH.sub.3).sub.2 Cl Cl ##STR195## C.sub.2 H.sub.5 orange 46613 N(CH.sub.3).sub.2 Cl Cl ##STR196## ##STR197## orange 46714 N(C.sub.2 H.sub.5).sub.2 Cl Cl ##STR198## ##STR199## orange 46715 N(C.sub.2 H.sub.5).sub.2 H H ##STR200## ##STR201## orange 45316 N(C.sub.2 H.sub.5).sub.2 H H ##STR202## C.sub.6 H.sub.5 orange 45217 N(C.sub.2 H.sub.5).sub.2 H H C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH C.sub.6 H.sub.5 orange 45218 N(CH.sub.3).sub.2 H H C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH C.sub.6 H.sub.5 orange 45219 CH.sub.3 H Cl ##STR203## C.sub.6 H.sub.5 orange 44420 CH.sub.3 H Cl ##STR204## ##STR205## orange 44521 N(CH.sub.3).sub.2 Cl Cl C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3 C.sub.3 H.sub.6 OCH.sub.3 orange 46522 NHC.sub.4 H.sub.9 Cl Cl ##STR206## C.sub.6 H.sub.5 orange 463__________________________________________________________________________ TABLE 14______________________________________ ##STR207## .lambda.maxNo. R.sup.1 R.sup.2 Hue (nm)______________________________________1 Cl C.sub.2 H.sub.4 OC.sub.4 H.sub.9 yellow 4262 Cl C.sub.3 H.sub.6 OC.sub.4 H.sub.9 yellow 4273 Cl C.sub.4 H.sub.9 (n) yellow 4284 Cl C.sub.3 H.sub.6 OC.sub.2 H.sub.5 yellow 4265 Cl C.sub.3 H.sub.6 OCH.sub.3 yellow 4276 Cl C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3 yellow 4277 CH.sub.3 C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3 yellow 4278 CH.sub.3 C.sub.3 H.sub.6 OCH.sub.3 yellow 4279 CH.sub.3 C.sub.3 H.sub.6 OC.sub.2 H.sub.5 yellow 42710 CH.sub.3 C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OH yellow 42711 Cl C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH yellow 42712 CH.sub.3 C.sub.3 H.sub.6 OC.sub.4 H.sub.8 OH yellow 427______________________________________ TABLE 15______________________________________ ##STR208## .lambda.maxNo. R.sup.1 R.sup.2 R.sup.3 Hue (nm)______________________________________ 1 C.sub.2 H.sub.4 OCH.sub.3 CH.sub.3 CH.sub.3 yellow 418 2 C.sub.2 H.sub.4 OCH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.5 yellow 419 3 C.sub.3 H.sub.6 OCH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.5 yellow 420 4 C.sub.3 H.sub.6 OCH.sub.3 CH.sub.3 CH.sub.3 yellow 418 5 C.sub.3 H.sub.6 OC.sub.2 H.sub.5 CH.sub.3 CH.sub.3 yellow 418 6 C.sub.3 H.sub.6 OC.sub.2 H.sub.5 C.sub.2 H.sub.5 C.sub.2 H.sub.5 yellow 420 ##STR209## C.sub.2 H.sub.5 C.sub.2 H.sub.5 yellow 419 ##STR210## C.sub.2 H.sub.5 C.sub.2 H.sub.5 yellow 420 ##STR211## C.sub.4 H.sub.9 (n) C.sub.4 H.sub.9 (n) yellow 422______________________________________

Claims

1. A compound of the formula ##STR212## wherein X.sup.1 is chlorine, bromine, methyl or trifluoromethyl, Y.sup.3 is chlorine or bromine, and K.sup.1 is a radical of the formula ##STR213## where R.sup.3 is C.sub.2 to C.sub.4 hydroxyalkyl, methoxyalkyl or methoxypropyl.

2. The compound of claim 1, which is: ##STR214##