DE1806582A1 - Monoazo dyes containing sulphonylbetaine groups for - cellulose acetate polamide polyurethane or poly- - Google Patents

Abstract

MONOAZO DYES CONTAINING SULPHONYLBETAINE GROUPS FOR CELLULOSE ACETATE, POLYAMIDE, POLYURETHANE OR POLYACRYLONITRILE FIBRES. G2A. Are of formula: and (II) in which N is not is quaternised with YZ where Y is a lower alkyl benzyl residue and Z - halogen, alkyl-sulphonic acid residue or a benzene or p-toluene sulphonic acid residue.

Description

Sulfonylbetaine-containing monoazo dyes and process for their preparation The present invention relates to new, sulfonylbetaine-containing monoazo dyes of the general formulas and in which R1 and R2 represent hydrogen atoms, alkyl groups with 1 - 4 carbon atoms, alkoxy groups with 1 - 4 carbon atoms, carboxylic acid groups or carboxylic acid alkyl ester groups with lower alkyl groups or in which R1 and R2 together are members of a phenyl ring which is formed by halogen atoms, preferably chlorine or bromine atoms, with alkyl groups 1 - 4 carbon atoms, alkoxy groups with 1 - 4 carbon atoms, lower alkyl sulfone, lower hydroxyalkyl sulfone or nitro groups can be substituted, R3 is a hydrogen or a halogen atom, preferably a chlorine or bromine atom, an alkyl group with 1 - 4 carbon atoms or a - Alkoxy group with 1 - 4 carbon atoms, R4 and R5 alkyl groups with 1 - 4 carbon atoms, which can be substituted by a hydroxyl group or together represent a pentamethylene radical, R6 an alkyl group with 1 - 4 carbon atoms which can be substituted by a hydroxyl group, or a Phenyl radical or in which R4, R5 or R6 together with the nitrogen atom represent a pyridinium or quinolinium radical, Y a lower alkyl group with 1-4 carbon atoms or the benzyl radical, X a hydrogen atom or an alkyl group with 1-4 carbon atoms, which can be substituted by a hydroxyl or cyano group, and Z - mean a halogen ion, an alkylsulfuric acid radical or a benzene or p-toluenesulfonic acid radical, as well as storage for their preparation, in which a) aromatic amines of the thiazole series of the general formula in which R1 and R2 have the meaning given above, diazotized and with coupling components of the general formula in which R3, R4, R5, R6 and X have the meanings given above, couples or b) compounds of the general formula in which R1, R2, 1, X, Y and Z have the meanings given above, with tertiary amines of the general formula in which R4, R5 and R6 have the meanings given above, whereupon the dyes of the formula (1) thus obtained are optionally converted with alkylating agents of the general formula YZ (8) in which Y and Z have the meanings given above, with formation of Treated dyes of the formula (2).

In the preparation of the dyes according to embodiment a) or in the preparation of the starting compounds of the above formulas (5) and (6) come as aromatic amines of the thiazole series, for example: 2-rmino-thiazole, 2-amino-4-methyl-thiazole, 2-amino-4, 5-dimethyl-thiazole, 2-amino-thiazole-5-carboxylic acid ethyl ester, 2-amino-5 ethoxy-benzothiazole, 2-amino-5-nitro-thiazole, 2-amino-benzehiazole, 2-mino-5-methyX-benzthiazole, 2-amino-5-chlorobenzothiazole, 2-amino-5,6-dimethylbenzthiazole, 2-amino-6-nitro-benzothiazole, 2-amino-6-methoxy-benzothiazole, 2-amino-6-ethoxy-benzothiazole, 2-amino-6-methylsulfonylbenzthiazole, 2-Amino-6-ethylsulfonyl-benzothiazole, 2-Amino-6- (2'-hydroxyethylsulfonyl) -benzthiazole, 2-Amino-5,6-dimethoxy-benzothiazole and 2-hmino-benzothiazole-6-carboxylic acid ethyl ester.

The coupling of the obtained from the amines of the general formula (3) Diazonium compounds with coupling components of the general formula (4) to the Dyes according to the invention is expediently acidic to neutral, preferably in the weakly acidic range between pH values of about 3 - 6.5. Possibly are additions of acid-binding agents, such as sodium acetate, magnesium carbonate or caustic soda, an advantage.

In the weakly acidic range, the process products fall immediately after the coupling process as colored suspensions and can for example can be isolated by filtration. Washing them out with water can keep them from sticking Electrolytes are freed.

In embodiment b) of the process according to the invention can Amines with three identical substituents, such as trimethylamine, triethylamine, Triethanolamine, tri-n-butylamine, tri-iso-butylamine or with various substituents, such as N, N-dimethylaniline, N, N-diethylaniline or N-ethyl-N-äthyl- anll in used will. Furthermore, those tertiary amines come into consideration in which two of the Substituents are linked in a ring, such as N-ethylpiperidine, or tertiary amines with aromatic character, such as pyridine or quinoline, The implementation of the starting compounds of the formula (5) or (6) with tertiary amines is preferably carried out in solvents at temperatures between about 0 ° and about 2000 ° C., preferably between about 200 and about 1600C, in particular between about 500 and about 160 C. The main solvents used here are benzene and its substitution products, such as toluene, chlorobenzene, o-dichlorobenzene, trichlorobenzenes or nitrobenzene, but also alcohols, dioxane, acetonitrile or dimethylformamide into consideration. It is the advantage of choosing the solvent so that the sulfonyl betaines formed are insoluble therein, which is the case with non-polar or slightly polar solvents is.

The tertiary amine and the vinylsulfonyl compound are generally used in a molar ratio of about 1: 1; in some cases, however, it is advantageous to to use the amine in excess. When using volatile amines, the Reaction can be carried out in a pressure vessel. Used as a tertiary amine trimethylamine used, this is advantageously gassed into the reaction solution.

The method according to embodiment b) can be, for example, as follows perform that the vinyl sulfone compound of formula (5) or (6) in one Solvent at boiling point dissolves or suspends and the tertiary amine is added the solution or suspension is added.

After a short time, the crystals begin to form Eliminate betains. Generally, the reaction will be in about 2 to 3 hours finished and the resulting dye can be removed by suction or centrifugation can easily be obtained in pure form.

To convert the dyes of the general formula (1) into their Quaternary salts of the general formula (2) include alkyl halides, such as, for example, methyl chloride Methyl iodide, ethyl bromide or butyl bromide, benzyl halides, especially benzyl chloride or benzyl bromide, dialkyl sulfates, such as dimethyl or diethyl sulfate and benzene and alkylbenzenesulfonates, such as methyl benzene or p-toluenesulfonate, into consideration. The reaction of the monoazo dyes cter formula (1) with alkylating agents is expediently carried out in an inert organic solvent, with the dyes of the formula (2) formed are eliminated. As an inert, organic solvent are for example benzene hydrocarbons, blue above and nitrobenzenes, higher-boiling aliphatic and alicyclic hydrocarbons and stable haloalkanes, such as carbon tetrachloride and tetrachlorethylene, as well as strongly polar solvents, such as dimethylfornamide or dimethyl sulfoxide, are suitable. The ones obtained in this way Dyes of the formula (2) are readily soluble in water and can be extracted from their aqueous Solutions can also be obtained by salting out, for example, with sodium chloride they can by adding zinc or cadmium chloride in di, corresponding double salts which are more difficult to dissolve in @@ sser.

The coupling components of the formula (4) used according to the process in embodiment a) can be prepared, for example, by the process of German patent application P 17 70 612.6. The starting compounds of the formula (5) used in embodiment b) can be obtained, for example, by adding hydroxy compounds of the general formula prepared in a customary manner by diazotization and coupling in which R1, R2, R3 and X have the meanings given above, reacts with vinylsulfonyl isocyanate or 2-chloroethylsulfonyl isocyanate with subsequent elimination of hydrogen, advantageously in the presence of an inert solvent and / or diluent. Quaternizing the compounds of the above formula (5) thus obtained with alkylating agents of the formula YZ, in which Y and Z have the meanings given above, then leads to the starting compounds of the above formula (6).

The new monoazo dyes of the general, prepared according to the process Formula (1) are as betaines in the range of the isoelectric point, which in general at pH values between 3 and 7 is practical in water, even at the boiling point insoluble, while even in dilute organic and inorganic acids, e.g.

Formic acid, acetic acid, hydrochloric acid or sulfuric acid, and also in Alkalis, e.g. ammonia or caustic soda, are easily soluble. So are the Process products of the formula (1) in their properties between the diluted in Acids and alkalis insoluble and the monoazo dyes which are already soluble in water.

If the water-insoluble dyes according to the invention are processed of formula (1) in the usual manner with dispersants to form dye preparations, see above one obtains dispersions which are based on synthetic fibers, such as cellulose triacet fibers, Cellulose-2 1/2-acet fibers, polyamide and polyurethane fibers, but especially on polyester fibers, such as polyethylene terephthalate fibers, with very good build-up prints of great color strength and high manufacturing and usage fastnesses, among which particularly the light and wet fastness as well as the thermal fastness are to be emphasized, result, These dyes are expediently used for dyeing polyester materials in the form of said paint preparations in aqueous suspension at temperatures above 100 ° C under pressure or at around 100 ° C with the addition of conventional carriers for use. They can also be used advantageously in such a way that they are woven or knitted made of polyester materials impregnated with suspensions of the new dyes, dries and then subjected to a brief exposure to heat, for example at 1900 - 21oOc.

These process products are also particularly suitable for dyeing Fiber blends that contain polyester components.

Dissolve the dyes of the formula (1) in dilute organic der inorganic acids, one can apply to fibers or fabrics made of tannin cotton, on polyacrylonitrile fibers or on fiber blends that contain polyacrylonitrile components, very deep and particularly lightfast colors obtained.

The water-soluble quaternary salts represented by the general formula (2) are particularly for dyeing materials made of tanned cotton, polyacrylonitrile fibers or of fiber blends that contain polyacrylonitrile components are suitable.

Example 1 7.5 parts by weight of 2-aninobenzothiazole are dissolved in 250 parts by volume of about 50 percent strength by weight sulfuric acid at about 80.degree. C., whereupon the solution is cooled to about -10.degree. C. while stirring. 40 parts by volume of a solution prepared by dissolving 140 parts by weight of sodium nitrite in 1500 parts by volume of concentrated sulfuric acid at about -5 ° C. are added at a maximum temperature of -50C. The mixture is then stirred for one hour at temperatures below 0 ° C. and then poured onto 500 parts by weight of ice, a light yellow to brownish, clear solution being formed in which the excess nitrous acid is destroyed by adding amidosulfonic acid. The mixture is then stirred into a solution of 19.6 parts by weight of the sulfonyl betaine of the formula at about OOC allowed to run in a mixture of 600 parts by volume of water and 50 parts by volume of glacial acetic acid, a blue-violet color immediately appearing. The pH-Vert is adjusted to about 3 by gradually adding 1000 parts by weight of crystalline sodium acetate during the coupling process, some of the dye formed already precipitating. After the end of the dropwise addition of the diazonium salt solution, the mixture is stirred for about 2 hours with external cooling and the remainder of the dye is then completely precipitated from the solution at about pH 5.5 by adding 180 parts by volume of sodium hydroxide solution of 400 Bé. One sucks off.

and washes the resulting red powder with water until the filtrate runs off electrolyte-free. Obtained after drying in vacuo at 7oOC one 23 parts by weight Dye, corresponding to a yield of about 84% of theory.

The red dye thus obtained is in benzene, xylene and chlorobenzene, practically insoluble in chloroform and in water even at the boiling point. He solves however, it can easily be found in half-concentrated hydrochloric acid and in acetic acid Cold with a blue-violet color and can be made from acetonitrile or better still from dimethylformamide be recrystallized. You use red needles with a melting point of 181 - 182 0C. The analysis of an uncrystallized sample gives the following values: Calc .: C 56.50 H 5.10 N 15.21 s 11.61 Found: C 56.0 H 5.2 N 15.1 S 11.5 One of one with Ealium bromide mixed and pressed sample shows infrared spectrum recorded below 6μ no pronounced band, which indicates the absence of a carbonyl function and thus speaks for the presence and remaining intact of the sulfonylbetaine residue.

From an aqueous dispersion, this dye on threads gives Woven or knitted fabrics made from polyethylene glycol terephthalate, good deep red colorations Lightfastness and from acetic acid solution are obtained on polyacrylonitrile blue-violet Dyeings of very good lightfastness.

To get to the water-soluble quaternary salt, 4 parts by weight are required of the dye obtained on the above-described lie in 150 parts by volume Dissolved dimethylformamide at 1200C, whereupon a solution of 4 parts by weight of dimethyl sulfate in 50 parts by volume of dimethylformamide was added dropwise with stirring at this temperature will. The initially deep red solution changes color from violet to pure blue. After the solvent has been distilled off in vacuo, it remains a Residue which, with blue color, is completely soluble in a little cold water. By adding a solution of 1.5 parts by weight of crystallized zinc chloride in 25 parts by volume of water turns the blue, clear solution into the quaternary salt of the dye precipitated as zinc chloride double salt. This addition connection is also good water-soluble and colors polyacrylonitrile from aqueous or weakly acidic solution in deep, red-tinged blue tones of excellent lightfastness.

Quaternary compounds with practically the same properties can can be obtained by adding excess methyl chloride to the dimethylformamide solution at about 70 ° C of the dye or, at about 500C internal temperature, methyl iodide to the dimethylformamide solution drips. The alkylation can also be carried out with benzyl chloride, with the change in color from red to blue, which is typical for quaternization, occurs.

Example 2 9.7 parts by weight of 2-amino-6-ethoxy-benzothiazole are dissolved at 90 ° C. in a mixture of 400 parts by volume of concentrated sulfuric acid and 100 parts by volume of gasse and then at -5 ° C. with stirring with the aid of 8.6. Parts by volume of a 43.6 percent by weight solution of nitrosylsulfuric acid in sulfuric acid are diazotized. After pouring onto about 600 parts by weight of finely crushed ice, a yellow, clear solution is obtained in which the excess nitrosylsulfuric acid is destroyed by adding amidosulfonic acid. It is coupled with a solution of 18.2 parts by weight of a sulfonyl betaine of the formula in 500 parts by volume of water and 50 parts by volume of glacial acetic acid at about 0 ° C. The dye, which is largely in solution in the acidic region after coupling, is precipitated in a readily filterable form by the gradual addition of sodium hydroxide solution of 400 Be at room temperature up to a pH of about 5.5. After suctioning off, washing out with water and drying 27 parts by weight, which corresponds to 95% of theory, of a red powder which is practically insoluble in benzene, xylene, chlorobenzene, acetonitrile and chloroform, as well as in water at high boiling point, is rather difficult to dissolve in hot o-dichlorobenzene or nitrobenzene and can be recrystallized well from dimethylformamide.

After recrystallization from dimethylformamide, red crystals are obtained, which melt at 172 ° C - 173 ° C. In acetic acid and in hydrochloric acid there is the dye already soluble in the cold.

Elemental analysis: Calc .: C 54.91 H 4.96 N 14.78 5 11.28 Found: C 54.3 H 5.1 N 14.4 S 11.1 From aqueous dispersion is obtained on polyester fibers or -weave intense red dyeings of good heat-setting fastness and from acetic acid Solution, pure blue shades of excellent are obtained on polyacrylonitrile material Lightfastness it.

To obtain the quaternary salt of the dye described above, 2.5 parts by weight of the dye in 150 parts by volume of o-dichlorobenzene Dissolved 120 ° C, whereupon a mixture of 5 parts by weight in this solution Dimethyl sulfate in 20 parts by volume of dimethyl sulfate in 20 parts by volume of o-dichlorobenzene with stirring is added dropwise at this temperature. After a few minutes, the initially discolored red solution over violet to blue, with the formed quaternary salt, which in o-dichlorobenzene is insoluble, is already beginning to crystallize. After everything is plugged up, the mixture is stirred for a further 15 minutes at the reaction temperature. Then through Cooling to room temperature completes the precipitation and the methosulfate formed the quartffir compound isolated by suction.

It can be done by dissolving in water and then salting out with sodium chloride or isolated as a double salt with zinc chloride. will. From watery or weak acidic solution, this dye gives pure blue colorations on polyacrylonitrile of excellent lightfastness.

In a manner similar to that described in Examples 1 and 2, the dyes mentioned in the table below are obtained: For R1 R2 R3 + X R4, own polyester polyacrylonitrile color of Polyacrylnitri game R5, color coloring from coloring from Quaternary Coloring of No. R6 aqueous acetic acid salt ++ quaternary salt + dispersion solution from aqueous solution m F1 o '180 "" G3 co 9 03 7 rl rl it s: ooir ba c r-, r (r s! ac: rn m pr rl C) (d O i-> VO 0 rl rl 1 P1 rl A co Q) 3 3 m U) r (l 3 = r c, rc'Oj OrJ rj 3 lt CII k red red reddish blue blue reddish blue ta oo rl CE I e) IO ç # +1 i It rl rd 6 lt d BolatU red rnr O cO 4;> 1 +3 OQ lt ur red red reddish blue blue reddish blue a> U, hD M ri r (t ( 6 lt CI brown-red violet-tinged blue-violet tinged rt rl -E, C rl tinged blue violet blue V do ç ç <« Y1 g C "from pJ rn F: tn rll -IFO nJ r rC Qd rl w «4 Od od HH 7 -C00C21.ts lt O Ci purple. he violet-tinged Q violet-tinged h P :: h blue 36cm R ç EI) Ss a ep P, sA to OCV ap.P * rd pl 0 0 O o .a-> o 8 3 M blue 2 M iCT) m E i X @ 3 Ci- red-violet blue-violet reddish blue-violet Co I violet blue O V O rl OQ a ol ia 2 M 4 M = PM Mt As> k nt > P 0 st b: UC) OQQQV >'a4 t st = UQ U > aa) m °> q + In o-position to the azo bridge ++ Y = CH3 Z- = CH3-O-SO3 - in examples 3 - 13 and 15 - 18 @@ - in example 14: With- R1 R2 R3 + X R4, own- polyester- Polyacrylonitrile color of the polyacrylonitrile game R5, color coloring from coloring from quaternary coloring of No. R6 aqueous acetic acid salt ++ quaternary salt + dispersion solution from aqueous solution @ o e, + r M ba Cr) Q, rc rc ri Q) .0 r (r (ACA 1 EI rl r ( 0 0 0 OU rd oj O 0 1-1 rl r (r (r (r (rl rl UC, YPP = I o 7 rn = r El Et 01 rI al Yc cd Irc rc a rl C9 Or (Or (Or (Q, 4) rl rl o es o ev oou r (+ I r (rl r ( C, C1 m I 1 7 1 wd blue 0 0 OQO 11 c4 ss mha: l t4 n s4 P: lhm hN N purple tinged blue 4th Cr C1 Q1 blue-red r ( rl rt CP rl O Red Blue $ f, P p HH 13 H -C3H7 Red. Red Blue @ mmh gl m al: M m «CI H blue r (p rc 15 H4X oooo S o P 4X 4n 4th 4 »4« red red or similar urr (O 0 f IO u -r O cJr (C, C1 af rt +) YV 0 «0« Hz OOO HdJ OOOO = p CH3 = PrS3MM ICIC <16C) F7 + CCI blue 18th c 22 q P: Pi 63 blue Q w O 0N>; eN O rd v XO to ° °° O 8th 00982 79 * ß Example 19 6.0 parts by weight of the compound are dissolved in 250 parts by volume of o-dichlorobenzene at 75 ° C., whereupon 1.5 parts by weight of pyridine are added to the clear, red solution while stirring. After a short time, crystals begin to separate out of the initially clear solution. After about 2 hours, the precipitated, violet-red colored sulfonylbetaine is filtered off and washed with methylene chloride. After drying, 5.5 parts by weight are obtained, corresponding to about 81.70 parts by weight of the theory of a red-violet dye which dyes polyethylene terephthalate materials in violet shades of very good heat resistance.

The vinylsulfonyl compound used as the starting compound of above formula can be obtained by following in usual manner, similar to example 1 executed, 2-amino-6-ethylsulfonylbenzthiazole and diazotized with N-di (2'-hydroxyethyl) -m-chloroaniline coupling, then the coupling product obtained is in the inert solvent, expediently in o-dichlorobenzene, in a molar ratio of about 1: 1 with vinyl sulfonyl isocyanate implemented.

In the above example, 2 parts by weight are used instead of pyridine Quinoline, the quinolium salt, which is also purple in color, is obtained while one by reading in excess trimethylamine into the hot o-dichlorobenzene solution can isolate the red-violet trimethylammonium compound after a short time.

Example 20 5 parts by weight of the compound are dissolved in 200 parts by volume of o-dichlorobenzene at 900C, whereupon 1.2 parts by weight of pyridine are added.

After a short time, red crystals begin to appear from the initially clear solution to precipitate, which melt at 172 - 173 ° C and in all properties with the after Example 2 obtained product are identical. A total of 5.1 parts by weight is obtained, corresponding to 89.5% of theory, dye.

The starting compound of the above formula can be behaved by one diazotized 2-amino-6-ethoxy-benzothiazole with N-methyl-N- (2t-hydroxyethyl) aniline couples and the coupling product reacts with vinyl sulfonyl isocyanate, or> by reacting N-methyl-N- (2'-hydroxyethyl) aniline with vinyl sulfonyl isocyanate and then coupling with the diazonium compound.

Claims (4)

P a t e n t a n s p r ü c h e: 1) Monoazo dyes of the general formulas containing sulfonylbetaine groups in which R1 and R2 represent hydrogen atoms, alkyl groups with 1 - 4 carbon atoms, alkoxy groups with 1 - 4 carbon atoms, carboxylic acid groups or carboxylic acid alkyl ester groups with lower alkyl groups or in which R1 and R2 together are members of a phenyl ring which is formed by halogen atoms, alkyl groups with 1 - 4 carbon atoms, alkoxy groups may be substituted with 1 - 4 carbon atoms, lower alkyl sulfone, lower hydroxyalkyl sulfone or nitro groups, R3 a hydrogen or a halogen atom, an alkyl group with n - 4 carbon atoms or: r an alkoxy group with 1 - 4 carbon atoms, R4 and R5 alkyl groups with 1 - 4 carbon atoms, which can be substituted by a hydroxyl group or together represent a pentamethylene radical, R6 is an alkyl group with 1 - 4 carbon atoms, which can be substituted by a hydroxyl group, or a phenyl radical, or in which R4 represents R5 or R6 together with the nitrogen atom a pyridinium or quinolinium radical b y mean a lower alkyl group with 1-4 carbon atoms. or the benzyl radical, X a hydrogen atom or an alkyl group with 1-4 carbon atoms, which can be substituted by a hydroxy or cyano group, and Z a halogen ion, an alkylsulfuric acid radical or a Mean benzene or p-toluenesulfonic acid radical. 2) Process for the preparation of sulfonylbetaine group-containing monoazo dyes of the general formulas in which R1 and h represent hydrogen atoms, alkyl groups with 1 - 4 carbon atoms, alkoxy groups with 1 - 4 carbon atoms, carboxylic acid groups or carboxylic acid alkyl ester groups with a lower alkyl group or in which R1 and R2 together are members of a phenyl ring which is formed by halogen atoms, alkyl groups with 1 ~ 4 carbon atoms, alkoxy groups with 1 - 4 carbon atoms, lower alkyl sulfone, lower hydroxyalkyl sulfone or nitro groups, R3 a hydrogen or a halogen atom, an alkyl group with 1 ~ 4 carbon atoms or an alkoxy group with 1 - 4 carbon atoms, R4 and R5 alkyl groups with 1 - 4 carbon atoms, which can be substituted by a hydroxyl group or together represent a pentamethylene radical, R6 represents an alkyl group with 1 - 4 carbon atoms which can be substituted by a hydroxyl group, or a phenyl radical, or in which R4, R5 or R together with the nitrogen atom represent a Pyridinium or quinolinium radical uten, Y is a lower alkyl group with 1-4 carbon atoms or the benzyl radical, n is a hydrogen atom or an alkyl group with 1-4 carbon atoms, which can be substituted by a hydroxyl or cyano group, and Z is a halogen ion, an alkylsulfuric acid radical or a benzene or p-Toluenesulfonic acid radical, characterized in that a) aromatic amines of the thiazole series of the general formula in which R1 and R2 have the meaning given above, diazotized and with coupling components of the general formula in which R3, R4, R5, R6 and X have the meanings given above, couples or b) compounds of the general formula in which R1, R2, R3, X, Y and Z e have the meanings given above, with tertiary amines of the general formula in which R4, R5 and R6 have the meaning given above, whereupon the dyes of the formula (1) thus obtained are optionally reacted with alkylating agents of the general formula Y - Z (8) in which Y and Z have the meaning given above, under Treated formation of dyes of formula (2). 3) use. of dyes of the general given in claim 1 Formula (1) for coloring and printing cellulose acetate, polyamide, polyurethane or Polyester fiber materials. 4) Use of dyes of the general specified in claim 1 Formula (2) for dyeing and printing tannin cotton or polyacrylonitrile fiber materials.