DE2817201A1 - AZO DYES - Google Patents

Description

The invention relates to dyes of the general formula I. in the

D the remainder of a sulfonamide group-free diazo component,

R is hydrogen, C [deep] 3- to C [deep] 5-alkenyl, optionally by hydroxy, C [deep] 1- to C [deep] 8-alkoxy, phenoxy, chlorine, bromine, cyano, C [deep] 1 - to C [deep] 4-alkanoyloxy, benzoyl or C1- to C [deep] 4-alkoxycarbonyl-substituted C [deep] 1- to C [deep] 5-alkyl, cyclohexyl, optionally substituted by methyl, ethyl, methoxy or ethoxy Phenyl or a radical of the formula

R [high] 1 hydrogen, methyl, ethyl, methoxy or ethoxy,

R [high] 2 hydrogen, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, C [low] 1- to C [low] 4-alkanoylamino, benzoylamino or C [low] 1- to C [low] 4-alkoxycarbonylamino ,

A [high] 1 a C [low] 2-C [low] 6-alkylene radical which may be interrupted by oxygen,

A [high] 2 hydrogen, optionally substituted by hydroxy or cyano C [low] 1-C [low] 4-alkyl, allyl or a radical A [high] 3,

A [high] 3 is a radical of the formula

-A [high] 4-XA [high] 5, or

A [high] 4 a C [low] 1-C [low] 6-alkylene radical which may be interrupted by oxygen,

A [high] 5 optionally substituted by hydroxy, chlorine, acetoxy or C [low] 1-C [low] 4-alkoxy C [low] 1-C [low] 4-alkyl or optionally by chlorine, methyl, methoxy or ethoxy substituted phenyl or naphthyl and

X -O- or, if A [high] 5 is optionally substituted phenyl or naphthyl, also mean a direct bond.

The radicals D of the diazo components come predominantly from the benzene, azobenzene or heterocyclic series, e.g. the thiophene, thiazole, thiadiazole, benzthiazole, benzisothiazole, thienoisothiazole, triazole, pyrazole or indazole series. Examples include:

Aniline, o-, m- or p-toluidine, o-, m- or p-methylsulfonylaniline, o-, m- or p-nitroaniline, o-, m- or p-cyananiline, o-, m- or p -Chloraniline, o-, m- or p-bromoaniline, o-, m- or p-trifluoromethylaniline, 3,4-dichloroaniline, 2,5-dichloroaniline, 3,5-dichloroaniline, 2,4,5-trichloroaniline, 2 , 4,6-trichloroaniline, 2,4,6-tribromaniline, 2,4-dicyananiline, 2,5-dicyananiline, 2-cyano-4-chloroaniline, 2-cyano-5-chloroaniline, 2-cyano-4-chloro -6-bromaniline, 2,4-dicyano-6-chloroaniline, 2,6-dicyano-4-chloroaniline, 2-chloro-4-cyananiline, 2,5-dichloro-4-cyananiline, 2,4,6-tricyananiline , 2-trifluoromethyl-4-chloroaniline, 2-nitro-4-chloroaniline, 2-nitro-4-methylaniline, 2-methyl-4-nitroaniline, 2-methoxy-4-nitroaniline, 2-chloro-4-nitroaniline, 2 -Bromo-4-nitroaniline, 2-trifluoromethyl-4-nitroaniline, 2-trifluoromethyl-4-nitro-6-bromoaniline, 2-trifluoromethyl-4-nitro-6-cyananiline, 2-trifluoromethyl-4-chloro-6-cyananiline , 2,5-dichloro-4-nitroaniline, 2,6-dichloro-4-nitroaniline, 2,6-dibromo-4-nitroaniline, 2-chloro-4-nitro-6-bromaniline, 2,6-D chloro-4-cyananiline, 2,4-dinitroaniline, 2,5-dinitro-6-chloroaniline, 2,4-dinitro-6-bromaniline, 2,4-dinitro-6-cyano-aniline, 2,6-dicyano 4-nitroaniline, 2-methylsulfonyl-4-chloro-aniline, 2-chloro-4-methylsulfonylaniline, 2-methylsulfonyl-4-nitroaniline, 2-nitro-4-ethylsulfonylaniline, 2,4-dintro-6-methylsulfonylaniline, 2- Cyan-4-methylsulphonylaniline, 2-phenylsulphonylaniline, 2,6-dichloro-4-methylsulphonylanilline, 2,6-dibromo-4-methylsulphonylaniline, o-, m- or p-aminobenzoic acid methyl ester, ethyl ester, propyl ester, butyl ester , benzyl ester, phenyl ester, small beta-methoxyethyl ester, -small beta-ethoxyethyl ester, -small beta-hydroxyethyl ester, 4-nitroanthranilic acid methyl ester, methoxyethyl ester, 3- or 4-

Aminophthalic acid, 5-aminoisophthalic acid or aminoterephthalic acid dimethyl ester, diethyl ester, 3- or 4-aminobenzoic acid amide, -methylamide, -n-butylamide, -methoxypropylamide, 2-, 3- or 4-aminobenzoic acid dimethylamide, -diethylamide, -pyrrolidide, -, N-methyl-N-small beta-hydroxyethylamide, 5-aminoisophthalic acid diamide, -dimethoxypropylamide, aminoterephthalic acid bis-diethylamide, 3- or 4-aminophthalic acid imide, -small beta-hydroxyethylimide, -phenylimide, 3-amino-6-nitro-phthalic acid- small beta-hydroxyethylimide, methylsulfonic acid-2´-, 3´- or 4´-aminophenyl ester, benzenesulfonic acid-2´-, 3´- or 4´-aminophenyl ester, N-acetyl-p-phenylenediamine, 2-aminobenzophenone, 1-aminoanthraquinone , 1-amino-4-chloroanthraquinone, 1-amino-2-ethoxynaphthalene, 4-aminonaphthalic acid butylamide, 6-amino-5,7-dicyanindane, 4-aminoazobenzene, 2´-, 3-dimethyl-4-aminoazobenzene, 3´, 2-dimethyl-4-aminoazobenzene, 2-methyl-5-methoxy-4-aminoazobenzene, 2-methyl-5-methoxy-4'-nitro-4-aminoazobenzene, 4-amino-2-nitroazobe nzol, 2,5-dimethoxy-4-aminoazobenzene, 2,5-dimethoxy-4´-nitro-4-aminoazobenzene, 2,5-dimethoxy-2´-6´-dichloro-4´-nitro-4-aminoazobenzene, 2,5-dimethoxy-2'-chloro-4'-nitro-4-aminoazobenzene, 4'-hydroxy-4-aminoazobenzene, 4'-chloro-4-aminoazobenzene, 3-chloro-4-aminoazobenzene, 2,3 ' -Dichloraminoazobenzene, 4´-chloro-3-aminoazobenzene, 3,5´-dibromo-4-amino-azobenzene, 2´- or 3´-chloro-4-aminoazobenzene, benzene-azo-4-aminonaphthalene, 4´-nitrophenylazo -4-aminonaphthalene, 2´, 6´-dichloro-4´-nitrophenylazo-4-aminonaphthalene, 2´-chloro-4´-nitrophenylazo-4-aminonaphthalene, 3-amino-2,1-benzisothiazole, 3-amino- 5-chloro-2,1-benzisothiazole, 3-amino-5-bromo-2,1-benzisothiazole, 3-amino-5-nitro-2,1-benzisothiazole, 3-amino-5-nitro-7-chloro

2,1-benzisothiazole, 3-amino-5-nitro-7-bromo-2,1-benzisothiazole, 3-amino-5,7-dichlorobenzisothiazole, 3-amino-5,7-dibromo-benzisothiazole, 4- Amino-7-nitro-1,2-benzisothiazole, 4-amino-5-chloro-7-nitro-1,2-benzisothiazole, 4-amino-5-bromo-7-nitro-1,2-benzisothiazole, 4- Amino-5-cyano-7-nitro-1,2-benzisothiazole, 2-aminothiazole, 2-amino-5-nitrothiazole, 2-amino-4-methyl-5-nitrothiazole, 2-amino-4-phenyl-5- nitrothiazole, 2-amino-5-phenyl-1,3,4-thiadiazole, 2-amino-5-ethylmercapto-1,3,4-thiadiazole, 3-phenyl-5-amino-1,2,4-thiadiazole, 3-small beta-carbomethoxyethylmercapto-5-amino-1,2,4-thiadiazole, 3-methylmercapto-5-amino-1,2,4-thiadiazole, 3-aminopyrazole, 3-amino-4-cyanpyrazole, 2-phenyl -3-amino-4-cyanpyrazole, 3-amino-5- (methyl-, ethyl-, phenyl- or benzyl) -pyrazole, 3-amino-1,2,4-triazole, 3-amino-5- (methyl -, ethyl, phenyl or benzyl) -1,2,4-triazole, 3-amino-1-phenyl-pyrazole, 3-aminopyridine, 3-aminoquinoline, 2-aminobenzothiazole, 2-amino-6-methylbenzthiazole, 2 -Amino-6- (methoxy-, ethoxy- or butoxy) -benzth iazole, 2-amino-6-cyanobenzthiazole, 2-amino-6-thiocyanato-benzthiazole, 2-amino-6-nitrobenzthiazole, 2-amino-5,6-dichlorobenzthiazole, 2-amino-6,7-dichlorobenzthiazole, 2- Amino- (4 or 6) -methylsulfonylbenzthiazole, 2-amino-3-nitro-5-methylsulfonylthiphene, 2-amino-3,5-bis (methylsulfonyl) -thiophene, 2-amino-3,5-dinitrothiphene, 2- Amino-3-cyano-5-nitro-thiophene, 2-amino-5-nitrothiophene, 5-amino-3-methyl-isothiazole or 3-amino-5-nitro- [2,3c] -thienoisothiazole.

Examples of radicals R include:

Methyl, ethyl, propyl, butyl, pentyl, isopropyl, isobutyl, isopentyl, allyl, butenyl, cyclohexyl, phenyl, methoxyphenyl, ethoxyphenyl, 2-phenoxyethyl, chloroethyl, bromoethyl, cyanoethyl, hydroxyethyl, 2,3-dihydroxypropyl, 2-hydroxypropyl, 2-hydroxybutyl, 2-hydrox-3-methoxypropyl, 3-hydroxypropyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-butoxyethyl, 2-benzoyloxyethyl, 2-acetoxyethyl, 2-propionyloxyethyl, 2-butyryloxyethyl, 2- Isobutyryloxyethyl, methoxycarbonylethyl, ethoxycarbonylethyl, propoxycarbonylethyl, butoxycarbonylethyl, isopropoxycarbonylethyl or isobutoxycarbonylethyl.

Residues R [high] 2 are in addition to those already mentioned in detail, for example:

Formylamino, acetylamino, propionylamino, methoxycarbonylamino, ethoxycarbonylamino or butoxycarbonylamino.

The radicals A [high] 1 are, for example, -CH [deep] 2CH [deep] 2- or C [deep] 2H [deep] 4OC [deep] 2H [deep] 4-.

A [high] 2 radicals are, in addition to hydrogen and A [high] 3, for example:

Methyl, ethyl, propyl, butyl, isobutyl, allyl, small beta-cyanoethyl or small beta-hydroxyethyl.

Residues A [high] 4 are for example:

-CH [deep] 2-, -C2H [deep] 4-, -CH [deep] 2CH [deep] 2CH [deep] 2-,

-CH [deep] 2CH [deep] 2OCH [deep] 2CH [deep] 2-, -CH [deep] 2CH [deep] 2CH [deep] 2OCH [deep] 2- or

The radicals A [high] 5 are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, methoxyethyl, ethoxyethyl, propoxyethyl, butoxyethyl, small beta-hydroxyethyl, small beta-hydroxypropyl, small beta-chloroethyl, small beta-acetoxyethyl, phenyl , Methoxyphenyl, ethoxyphenyl, methylphenyl, dimethylphenyl, chlorophenyl or naphthyl.

Compounds of formula II is obtained, for example, from compounds of the formula III by reaction with compounds of the formula or from compounds of the formula

By implementation with compounds of the formulas

O = C = N-A [high] 3

or

The reactions are expediently carried out in aprotic solvents.

The reactions are known in principle, details can be found in the examples, in which parts and percentages relate to weight, unless otherwise stated.

Dyes of the formula Ia are of particular importance in the

R [high] 3 C [low] 1-C [low] 4-alkyl, allyl, small beta-cyanoethyl, C [low] 1-C [low] 4-alkoxyethyl or propyl, phenoxyethyl or propyl or Phenyl,

R [high] 4 hydrogen, methyl or methoxy,

R [high] 5 hydrogen, methyl, methoxy, chlorine, acetylamino or propionylamino,

A [high] 6 -CH [low] 2CH [low] 2-, or

A [high] 7 hydrogen, methyl, ethyl, allyl, methoxyethyl or ethoxyethyl,

A [high] 8 -CH [low] 2CH [low] 2-, -CH [low] 2CH [low] 2CH [low] 2-,

-CH [deep] 2CH [deep] 2OCH [deep] 2CH [deep] 2-, -CH [deep] 2CH [deep] 2CH [deep] 2OCH [deep] 2- or -CH [deep] 2CH [deep] 2CH [deep] 2OCH [deep] 2CH [deep] 2-,

A [high] 9 C [low] 1- to C [low] 4-alkyl, small beta-hydroxyethyl or phenyl

and D and X have the meanings given.

The radicals D preferably come from the benzene, thiophene, thiazole, thiadiazole, benzthiazole, benzisothiazole or azobenzene series.

Preferred diazo components are, for example, those of the formula in the

T [high] 1 hydrogen, chlorine, bromine, nitro, cyano, methylsulfonyl, ethylsulfonyl, phenylsulfonyl or C [low] 1- to C [low] 4-alkoxycarbonyl,

T [high] 2 nitro, cyano, hydrogen, chlorine, bromine, methylsulfonyl, ethylsulfonyl or phenylazo and

T [high] 3 are hydrogen, chlorine, bromine, nitro or cyano as well

2-amino-5-nitrothiophene, 2-amino-3,5-dinitrothiophene, 2-amino-3-cyano-5-nitrothiophene, 2-amino-3-nitro-5-methylsulfonylthiophene, 3-amino-5-chloro 2,1-benzisothiazole, 3-amino-5-bromo-2,1-benzisothiazole, 3-amino-5-nitro-2,1-benzisothiazole, 3-amino-5-nitro-7-chloro-2,1- benzisothiazole, 3-amino-5-nitro-7-bromo-benzisothiazole, 4-amino-7-nitro-1,2-benzisothiazole, 4-amino-5-chloro-7-nitro-1,2-benzisothiazole,

4-Amino-5-bromo-7-nitro-1,2-benzisothiazole, 4-amino-5-cyano-7-nitro-1,2-benzisothiazole, 2-amino-5-nitrothiazole, 2-amino-5- ethylmercapto-1,3,4-thiadiazole, 3-phenyl-5-amino-1,2,4-thiadiazole, 3-small beta-carbomethoxyethylmercapto-5-amino-1,2,4-thiadiazole, 3-methylmercapto-5 -amino-1,2,4-thiadiazole, 2-amino-6-methoxybenzthiazole, 2-amino-6-cyanobenzthiazole, 2-amino-6-thiocyanatobenzothiazole, 2-amino-6-nitrobenzthiazole, 2-amino-5,6 dichlorobenzothiazole, 2-amino-6,7-dichlorobenzothiazole or 2-amino-6-methylsulfonylbenzthiazole.

The dyes of the formula I are suitable for dyeing synthetic and semi-synthetic fibers, e.g. cellulose acetates, polyamides and especially polyesters. The dyeings obtained have good light, wet and heat-setting fastness properties.

Some of the dyes are also suitable for the process described in German Patent 1,811,796.

example 1

15 parts of N-ethyl-N-phenoxycarbonyloxäthyl-m-toluidine are dissolved in 50 parts of toluene and 7.8 parts of 2- (2-hydroxyethoxy) ethylamine are added dropwise at a temperature of 45-60 ° C. After three hours of stirring at 50-60 ° C., the mixture is cooled to room temperature and the toluene solution is extracted first twice with dilute sodium hydroxide solution and then three times with water. The toluene solution is dried over sodium sulfate and then the solvent is distilled off under reduced pressure. 14.5 parts of an oil remain. The compound of the formula thus obtained is processed further without cleaning.

Example 2

7.2 parts of 2-amino-5-nitrothiazole are introduced into 20 parts of 96% sulfuric acid at 10-15 ° C., 100 parts of a mixture of glacial acetic acid and propionic acid (17: 3) are slowly added at this temperature and Diazotized 5 ° C with 15.5 parts of 45% nitrosylsulfuric acid. After 4 hours, the diazo solution thus obtained is at 0-5 ° C to a solution of 15.5 parts of N-ethyl-N- (2-hydroxyäthoxyäthylcarbamoyloxäthyl) -m-toluidine in 30 parts of concentrated hydrochloric acid, 250 parts of water and 250 parts of ice added dropwise. A pH of 1.3 is set by adding sodium acetate. After the coupling has ended, the dyestuff which has precipitated out is filtered off with suction, washed neutral with water and dried at 40.degree. C. under reduced pressure. 13 parts of the dye of the formula are obtained which provides blue dyeings with good fastness properties on polyesters and cellulose esters.

Example 3

5.5 parts of 4-amino-5-cyano-7-nitro-benzisothiazole- (1,2) are added to an acid mixture of 50 parts of 85% sulfuric acid and 15 parts by volume of glacial acetic acid / propionic acid (17: 3) at 10 ° C. registered. 9 parts of 45% strength nitrosylsulfuric acid are added dropwise at 0-5 ° C. and the mixture is stirred at this temperature for 4 hours. The excess nitrite is destroyed by adding urea and the resulting diazo solution is added dropwise at 0-5 ° C to a solution of 8.2 parts of N-ethyl-N- (small beta-phenylethylcarbamoyloxethyl) -m-toluidine in 15 parts of concentrated hydrochloric acid, 15 parts of dimethylformamide, 125 parts of water and 125 parts of ice. A pH of 1.2 is then set by adding sodium acetate. After the coupling has ended, the dyestuff which has precipitated out is filtered off with suction, washed neutral and dried at 60 ° C. under reduced pressure. 10 parts of the dye of the formula are obtained which provides intensive dyeings with very good fastness properties on polyesters.

Example 4

10.4 parts of 2,6-dichloro-4-nitroaniline are dissolved in 50 parts of 85% strength sulfuric acid and diazotized at 0-5 ° C. with 16 parts of 45% strength nitrosylsulfuric acid. After 5 hours, the resulting diazonium salt solution is at 0-5 ° C in a solution of 14.6 parts of N-cyanoethyl-N-small beta-methoxyäthylcarbamoyloxäthyl-aniline in 30 parts of concentrated hydrochloric acid, 30 parts of dimethylformamide, 250 parts

Pour in water and 250 parts of ice. A pH of 1.0 is set by adding sodium acetate. After the coupling has ended, the dyestuff which has precipitated out is filtered off with suction, washed neutral with water and dried at 60.degree. C. under reduced pressure. 23.5 parts of the dye of the formula are obtained which provides yellow-brown dyeings with good fastness properties on polyester fibers.

Example 5

7.4 parts of 3-methylmercapto-5-amino-1,2,4-thiadiazole are introduced into 200 parts of a mixture of glacial acetic acid and propionic acid (17: 3), 60 parts of 85% strength sulfuric acid are added dropwise and at 0-5.degree is diazotized with 15.5 parts of 45% nitrosylsulfuric acid. After 4 hours, the resulting diazonium salt solution is at 0-5 ° C to a solution of 14.6 parts of N-cyanoethyl-n-small beta-methoxyäthylcarbamoyloxyäthylaniline in 30 parts of concentrated hydrochloric acid, 30 parts of dimethylformamide, 250 parts of water and 250 parts Let the ice flow in. After finished

Coupling, the dyestuff which has precipitated out is filtered off with suction, washed neutral with water and dried at 60.degree. C. under reduced pressure. 15 parts of the dye of the formula are obtained which provides red dyeings with good fastness properties on polyesters and cellulose esters.

Example 6

8.1 parts of 2-cyano-4-nitroaniline are dissolved in 50 parts of concentrated sulfuric acid and diazotized at 0-5 ° C. with 16 parts of 45% strength nitrosylsulfuric acid. After 5 hours, the excess nitrite is destroyed with urea and the solution is filtered. The diazo solution thus obtained is added dropwise at 0-5 ° C. to a solution of 14.9 parts of N-ethyl-N-benzylcarbamoyloxäthylaniline in 30 parts of concentrated hydrochloric acid, 30 parts of dimethylformamide, 250 parts of water and 250 parts of ice. A pH of 1.0 is set by adding sodium acetate. After the coupling has ended, the dyestuff which has precipitated out is filtered off with suction, washed neutral and dried at 60.degree. C. under reduced pressure. 20 parts of the dye of the formula are obtained

which provides violet dyeings with good fastness properties on polyester fibers.

Example 7

14.4 parts of the dye from Example 47.5 parts of pyridine, 60 parts of dimethylformamide and 4.5 parts of copper (I) cyanide are heated at 90-100 ° C. for 3 hours. The cooled solution is poured into 500 parts of water, filtered off with suction and the residue is introduced into a solution of 10 parts of iron (III) chloride in 150 parts of 10% strength hydrochloric acid. After stirring overnight, the dye is filtered off with suction, washed neutral and dried at 50 ° C. under reduced pressure. 9.5 parts of the dye of the formula are obtained which provides blue dyeings with good fastness properties on polyesters.

Analogously to the methods described, the dyes which are identified in the table below by specifying the substituents and which result in dyeings in the specified hue on polyester fibers are also obtained.

<Table continuation>

Claims (4)

1. Azo dyes of the general formula in the D the remainder of a sulfonamide group-free diazo component, R is hydrogen, C [deep] 3- to C [deep] 5-alkenyl, optionally by hydroxy, C [deep] 1- to C [deep] 8-alkoxy, phenoxy, chlorine, bromine, cyano, C [deep] 1 - to C [deep] 4-alkanoyloxy, benzoyl or C1- to C [deep] 4-alkoxycarbonyl-substituted C [deep] 1- to C [deep] 5-alkyl, cyclohexyl, optionally substituted by methyl, ethyl, methoxy or ethoxy Phenyl or a radical of the formula R [high] 1 hydrogen, methyl, ethyl, methoxy or ethoxy, R [high] 2 hydrogen, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, C [low] 1- to C [low] 4-alkanoylamino, benzoylamino or C [low] 1- to C [low] 4-alkoxycarbonylamino , A [high] 1 a C [low] 2-C [low] 6-alkylene radical which may be interrupted by oxygen, A [high] 2 hydrogen, optionally substituted by hydroxy or cyano C [low] 1-C [low] 4-alkyl, allyl or a radical A [high] 3, A [high] 3 is a radical of the formula -A [high] 4-XA [high] 5, or A [high] 4 a C [low] 1-C [low] 6-alkylene radical which may be interrupted by oxygen, A [high] 5 optionally substituted by hydroxy, chlorine, acetoxy or C [low] 1-C [low] 4-alkoxy C [low] 1-C [low] 4-alkyl or optionally by chlorine, methyl, methoxy or ethoxy substituted phenyl or naphthyl and X -O- or, if A [high] 5 is optionally substituted phenyl or naphthyl, also mean a direct bond. 2. Dyestuffs according to Claim 1 of the formula Ia in the R [high] 3 C [low] 1-C [low] 4-alkyl, allyl, small beta-cyanoethyl, C [low] 1-C [low] 4-alkoxyethyl or propyl, phenoxyethyl or propyl or Phenyl, R [high] 4 hydrogen, methyl or methoxy, R [high] 5 hydrogen, methyl, methoxy, chlorine, acetylamino or propionylamino, A [high] 6 -CH [low] 2CH [low] 2-, or A [high] 7 hydrogen, methyl, ethyl, allyl, methoxyethyl or ethoxyethyl, A [high] 8 -CH [low] 2CH [low] 2-, -CH [low] 2CH [low] 2CH [low] 2-, -CH [deep] 2CH [deep] 2OCH [deep] 2CH [deep] 2-, -CH [deep] 2CH [deep] 2CH [deep] 2OCH [deep] 2- or -CH [deep] 2CH [deep] 2CH [deep] 2OCH [deep] 2CH [deep] 2-, A [high] 9 C [low] 1- to C [low] 4-alkyl, small beta-hydroxyethyl or phenyl and D and X have the meanings given. 3. Process for the preparation of azo dyes according to Claim 1, characterized in that a diazonium compound of amines of the formula DNH [deep] 2 with coupling components of the formula implements. 4. Use of the dyestuffs according to Claim 1 for dyeing textile material made from synthetic and semi-synthetic fibers.