EP2032659A2

EP2032659A2 - Disperse dyes, production and use

Info

Publication number: EP2032659A2
Application number: EP07729953A
Authority: EP
Inventors: Andreas Endres
Original assignee: Dystar Textilfarben GmbH and Co Deutschland KG
Current assignee: Dystar Colours Distribution GmbH
Priority date: 2006-06-14
Filing date: 2007-06-06
Publication date: 2009-03-11
Also published as: WO2007144298A2; MX2008015961A; DE102006027535A1; BRPI0712753A2; US20090209742A1; CA2655255A1; TW200808910A; JP2009540077A; KR20090016558A; CN101454402A; WO2007144298A3

Abstract

The present invention provides dyes of the general formula (I) where X and R<SUP>1</SUP> to R<SUP>5</SUP> are each as defined in claim 1, processes for their production and their use.

Description

Disperse dyes, their preparation and their use

The present invention relates to disperse dyes comprising an N-substituted phthalimide diazo component and an aniline series coupling component, to processes for their preparation and to their use for dyeing textile materials.

Disperse dyes of this type are already known and described, for example, in FR 1, 358,145, US Pat. No. 3,980,634, US Pat. No. 4,039,522, EP 0 051 563 A1, EP 0 443 984 A1, EP 0 667 376 A1, WO 00/40656, WO 02/68539, WO 02 / 74864 and WO 04/44058. However, they have some disadvantages and, for example, do not meet today's needs for certain wash fastnesses.

It has now surprisingly been found that the dyes defined below meet the stated requirements and also have a better build-up, better temperature dependence of the dyeing and higher pH stability.

The present invention relates to dyes of the general formula (I)

wherein

X ¹ and X ^{2 are} both hydrogen or both cyan; R ¹ is ethyl, straight-chain or branched (C ₃ -C _O) -alkyl or - (CH ₂₎ _n COOR ^6; R ^{2 is} hydrogen, methyl, cyanomethyl, halomethyl, ethyl, cyanoethyl,

Haloethyl, halo, -NH-CO-R ⁷ or -NH-SO ₂ -R ⁷ ; R ³ (C _r C ₈₎ -alkyl or by hydroxy, (CrC ₄₎ -alkoxy, cyano, halogen, -OCOR ^7, COOR ^7, phenyl, vinyl or substituted (C _r C ₈₎ alkyl; R ⁴ is hydrogen, (CrC ₈₎ -alkyl or by hydroxy, (CrC ₄₎ -alkoxy, cyano, halogen, -OCOR ^7, COOR ^7, phenyl, vinyl or substituted (dC ₈₎ alkyl;

R ⁵ is hydrogen, halogen, (CrC ₄₎ alkyl, (C _r -C ₈₎ -alkoxy or by halogen,

Cyano or phenyl substituted (C 1 -C ₈ ) alkoxy; R ^{6 is} (C 1 -C ₄ ) -alkyl;

R ⁷ (Ci-C ₈₎ alkyl or halogen- or cyano-substituted (CrC ₈₎ alkyl; and n is 1, 2, 3, 4 or 5; mean, where

Compounds in which R ^{1 is} ethyl or n-butyl, X ¹ and X ^{2 are} both cyano and R ^{2 is} -NH-CO-R ⁷ , with R ⁷ = C _r alkyl;

Compounds in which R ^{1 is} ethyl or n-butyl, X ¹ and X ^{2 are} both hydrogen and R ² - NH-CO-R ⁷ or -NH-SO ₂ -R ⁷ ;

the compound in which R ^{1 is} - (CH ₂ ) _n COOR ⁶ with n = 2 and R ⁶ = C _r alkyl, X ¹ and X ^{2 are} both hydrogen, R ^{2 is} -NH-CO-R ⁷ with R ⁷ = C ₂ alkyl, one of the radicals R ³ and R ^{4 is} C ₂ - alkyl and the other by -OCOR ⁷ substituted C ₂ alkyl with R ⁷ = d-alkyl and R ^{5 is} hydrogen;

Compounds in which R ^{1 is} branched C ₃ -alkyl, X ¹ and X ^{2 are} both hydrogen, R ^{2 is} -NH-CO-R ⁷ with R ⁷ = C ₃ -alkyl, the radicals R ³ and R ^{4 are} both C ₂ - Alkyl and R ^{5 are} hydrogen; and

Compounds in which R ^{1 is} isobutyl, X ¹ and X ^{2 are} both hydrogen, R ^{2 is} -NH-CO-R ⁷ where R ⁷ = C ₆ -alkyl or -NH-SO ₂ -R ⁷ where R ⁷ = d-alkyl, the radicals R ³ and R ^{4 are} both C ₂ alkyl and R ^{5 is} hydrogen;

excluded are. For R ¹ standing straight-chain (C ₃ -C ₀₎ alkyl may, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-propyl be n-Octly, n-nonyl or n-decyl.

Branched (C ₃ -C ₁₀ ) -alkyl which stands for R ¹ can be, for example, isopropyl, isobutyl, sec-butyl or tert-butyl. Straight chain (C ₃ -C _O) alkyl is preferred. If R ^{1 is} ethyl or n-butyl, R ^{2 is} preferably cyanomethyl, halomethyl, ethyl, cyanoethyl, haloethyl, halogen, -NH-CO-R ⁷ or -NH-SO ₂ -R ⁷ ; In particular, R ² -NH-CO-R ⁷ is acetylamino and propionylamino, while R ² -NH-SO ² -R ^{7 is} in particular methylsulfamino and ethylsulfamino.

For R ³ or R ⁷ , (C 1 -C ₈ ) -alkyl or substituted (C 1 -C ₈ ) -alkyl can be straight-chain or branched and is, for example, methyl, ethyl, n- or iso-

Propyl, n-, iso-, sec- or tert-butyl or straight-chain or branched pentyl,

Hexyl, heptyl or octyl. Is preferably (C _T C ^ alkyl, and particularly preferred are

Methyl and ethyl.

The same applies to (C ₁ -C ₄ ) -alkyl which stands for R ⁶ and thus preferably represents methyl or ethyl, and also represents (C ₁ -C ₈ ) -alkoxy which stands for R ⁵ and which is accordingly preferred (C ₁ - ₎ .

C ₄ ) alkoxy and particularly preferably methoxy or ethoxy. (C 1 -C ₄ ) -alkoxy, which is a substituent of one of R ³ or R ⁴

(C 1 -C ₈ ) -alkyl radical, is also preferably methoxy or ethoxy.

Halogen is preferably fluorine, chlorine or bromine and particularly preferably chlorine or bromine.

R ⁵ is preferably hydrogen.

Preferred dyes according to the invention correspond to the general formula (Ia)

wherein

R ^{1 is} n-pentyl or - (CH ₂ ) _n COOR ⁶ ;

R ^{2 is} methyl, -NH-CO-methyl or -NH-SO ₂ -methyl;

R ³ and R ^{4 are} independently ethyl, - (CH ₂ J ₂ CN, - (CH ₂ ) ₂ OMe, - (CH ₂ ) ₂ OAc, or n-butyl;

R ^{6 is} methyl, ethyl or butyl; and n 1, 2 or 3; mean.

Preferred dyes according to the invention also correspond to the general formula (Ib)

wherein

R ^{1 is} ethyl or - (CH ₂ ) _n COOR ⁶ ;

R ^{6 is} methyl, ethyl or butyl; and n is 1, 2, 3 or 5; mean.

Preferred dyes according to the invention also correspond to the general formula (Ic)

wherein

R ^{1 is} iso-propyl, iso-butyl, sec-butyl or tert-butyl; and R ³ and R ^{4 are} independently ethyl, - (CH ₂ ) ₂ CN, - (CH ₂ ) ₂ OMe, - (CH ₂ ) ₂ OAc, or n -butyl; mean.

The dyes of the general formula (I) according to the invention can be prepared by methods known to the person skilled in the art.

Thus, for example compounds of the invention obtained, in which X ¹ and X ² are both cyano, characterized in that a compound of general formula (II) wherein R ¹ to R ⁵ are defined as indicated above, cyanated.

The cyanation is preferably carried out in a known manner, for example with a mixture of copper (I) cyanide and zinc (II) cyanide in the presence of potassium iodide and imidazole in hot NMP.

The compounds of the general formula (II) can be prepared by diazotizing a compound of the general formula (III)

and coupling to a compound of general formula (IV)

wherein R ² to R ⁵ are defined as indicated above.

The diazotization of the compounds of the general formula (III) is generally carried out in a known manner, for example with sodium nitrite in acidic, for example hydrochloric or sulfuric acid aqueous medium or with nitrosyl sulfuric acid in dilute sulfuric acid, phosphoric acid or in a mixture of acetic and propionic acid , The preferred temperature range is between 0 ⁰ C and 15 ° C.

The coupling of the diazotized compounds to the compounds of the general formula (IV) is generally likewise carried out in a known manner, for example in acidic, aqueous, aqueous-organic or organic medium, particularly advantageously at temperatures below ^10.degree. C. The acids are used in particular Sulfuric acid, acetic acid or propionic acid. The compounds of the general formula (IV) are known and can be prepared by known methods.

The compounds of the general formula (III) can be prepared, for example, starting from phthalimide as follows.

Phthalimide is nitrated, for example, as described in Organic Synthesis, CV 2, page 459 (δ.Aufl) and the resulting 4-nitrophthalimide converted by treatment with sodium hydroxide in 4-nitrophthalic acid. From this, one molecule of water can be removed by heating with acetic anhydride and thus the corresponding anhydride can be obtained. This is reacted with an amine of the general formula (V)

R ¹ -NH ₂ (V) wherein R ^{1 is} as defined above, to the compound of the general formula

(VI)

wherein R ^{1 is} as defined above, reacted.

The reaction of the phthalic anhydride with the amine of the general formula (VI) is preferably carried out in such a way that the phthalic anhydride is introduced into the amine and allowed to react for several hours at elevated temperature.

By reduction of the compound of the general formula (VI), the compound of the general formula (VII) can then be

wherein R ¹ is defined as indicated above. The reduction is advantageously carried out according to the method described in Chem. Pharm. Bull. 42 (9), 1994, page 1817.

Finally, bromination in glacial acetic acid gives the compound of general formula (III) from the compound of general formula (VII). If in the above diazotization and coupling reaction in place of a compound of the general formula (III) a compound of general formula (VII), as are dyes of the general formula (I) of the invention wherein X ¹ and X ² are both hydrogen stand, received. The latter dyes according to the invention are thus obtainable by reacting a compound of the general formula (VII)

wherein R ^{1 is} as defined above, diazotized and to a compound of general formula (IV)

wherein R ² to R ⁵ are defined above coupled.

The dyes of the general formula (I) according to the invention are outstandingly suitable for dyeing and printing hydrophobic materials, the dyeings and prints obtained being characterized by level shades and high use fastnesses. Particularly noteworthy are good fastness to light, thermosetting, water and perspiration, in particular very good wash fastnesses, as well as the high reduction stability. The said hydrophobic materials may be of synthetic or semi-synthetic origin.

The present invention thus also relates to the use of the dyes of the general formula I for dyeing and printing hydrophobic materials or processes for dyeing or printing such materials in per se conventional procedures, in which one or more dyes of the general formula ( I) as a colorant. As hydrophobic materials are, for example, cellulose 2 ¹ /4-acetate, cellulose triacetate, polyamides and especially high molecular weight polyesters into consideration. High molecular weight polyester materials are especially those based on polyethylene glycol terephthalates. The hydrophobic synthetic materials may be in the form of flat or thread-like structures and be processed for example into yarns or woven, knitted or knitted fabrics. Preference is given to fibrous textile materials which may be present, for example, in the form of microfibers.

The dyeing according to the invention use can be carried out in manner known per se, preferably from aqueous dispersion, if appropriate in the presence of carriers, between 80 to about 110 ⁰ C by the exhaust method or by the HT method in a dyeing autoclave at 110 to 140 ⁰ C, and after the so-called heat-setting process, the goods are padded with the dyeing liquor and then fixed at about 180 to 230 ⁰ C.

The printing of the materials mentioned can be carried out in a manner known per se so that the dyestuffs of the general formula (I) according to the invention are incorporated into a printing paste and the goods printed therewith for fixing the dyestuff, if appropriate in the presence of a carrier, at temperatures between 180 to 230 ⁰ C with HT-steam, pressure steam or dry heat is treated.

When used in dyeing liquors, padding liquors or printing pastes, the dyestuffs of the general formula (I) according to the invention should be in the finest possible distribution.

The fine distribution of the dyes is carried out in manner known per se, by slurrying the dye obtained in the fabrication together with dispersants in a liquid medium, preferably in water, and exposing the mixture to the action of shear forces, the originally present dye particles mechanically so far be crushed that an optimum specific surface area is achieved and the sedimentation of the dye is minimized. This is done in suitable mills, such as ball or sand mills. The Particle size of the dyes is generally between 0.5 and 5 microns, preferably about 1 micron.

The dispersants co-used in the milling process may be non-ionic or anionic. Nonionic dispersants are, for example, reaction products of alkylene oxides, such as ethylene or

Propylene oxide with alkylatable compounds, such as fatty alcohols, fatty amines, fatty acids, phenols, alkylphenols and carboxylic acid amides. Anionic dispersants are, for example, lignosulfonates, alkyl or alkylarylsulfonates or alkylaryl polyglycol ether sulfates.

The dye formulations thus obtained should be pourable for most applications. The dye and dispersant content is therefore limited in these cases. Generally, the dispersions are adjusted to a dye content of up to 50 percent by weight and a dispersant content of up to about 25 percent by weight. For economic reasons, dye contents of 15 percent by weight are usually not exceeded.

The dispersions may also contain other auxiliaries, for example those which act as oxidizing agents, for example sodium m-nitrobenzenesulfonate or fungicidal agents, for example sodium o-phenylphenolate and sodium pentachlorophenolate and, in particular, so-called "acid donors", such as butyrolactone, monochloroacetamide, sodium chloroacetate, sodium dichloroacetate, the Na salt of 3-chloropropionic acid, half esters of sulfuric acid such as lauryl sulfate, and sulfuric acid esters of ethoxylated and oxypropylated alcohols such as butyl glycol sulfate.

The dye dispersions thus obtained can be used very advantageously for the approach of dyeing liquors and printing pastes.

For certain applications, powder settings are preferred. These powders contain the dye, dispersants and other adjuvants, such as wetting agents, antioxidants, preservatives and dedusting agents, and the abovementioned "acid donors".

A preferred manufacturing method for powdered dye preparations is that the liquid dye dispersions described above Liquid is withdrawn, for example by vacuum drying, freeze-drying, by drying on drum dryers, but preferably by spray drying.

To prepare the dyeing liquors, the required amounts of the dye formulations described above are diluted with the dyeing medium, preferably with water, to such an extent that a liquor ratio of 1: 5 to 1:50 results for the dyeing. In addition, further dyeing auxiliaries, such as dispersants, wetting agents and fixing aids, are generally added to the liquors. By adding organic and inorganic acids such as acetic acid, succinic acid, boric acid or phosphoric acid, a pH of 4 to 5, preferably 4.5, adjusted. It is advantageous to buffer the adjusted pH and to add a sufficient amount of a buffer system. An advantageous buffer system is, for example, the acetic acid / sodium acetate system.

If the dye or the dye mixture to be used in textile printing, the required amounts of the above dye settings in a conventional manner together with thickeners, such as alkali alginates or the like, and optionally other additives, such as fixing accelerators, wetting agents and Oxidizing agents, kneaded to printing pastes.

The present invention also relates to inks for digital textile printing by the ink-jet process, which are characterized in that they contain a dye of the general formula (I) according to the invention.

The inks according to the invention are preferably aqueous and comprise one or more of the dyes of the general formula (I) according to the invention, for example in amounts of from 0.1 to 50% by weight, preferably in amounts of from 1 to 30% by weight and more preferably in Amounts of 1 to 15 wt .-% based on the total weight of the ink. In addition, they contain in particular from 0.1 to 20 wt .-% of a dispersant. Suitable dispersants are known in the art, are commercially available and include, for example, sulfonated or sulfomethylated lignins, condensation products of aromatic sulfonic acids and formaldehyde, condensation products of optionally substituted phenol and formaldehyde, Polyacrylates and corresponding copolymers, modified polyurethanes and reaction products of alkylene oxides with alkylatable compounds, such as fatty alcohols, fatty amines, fatty acids, carboxylic acid amides and optionally substituted phenols.

Furthermore, the inks of the invention may contain the usual additives, such as viscosity moderators to adjust viscosities in the range of 1, 5 to 40.0 mPas in a temperature range of 20 to 50 ⁰ C. Preferred inks have a viscosity of 1.5 to 20 mPas and particularly preferred inks have a viscosity of 1.5 to 15 mPas.

Suitable viscosity moderators are theological additives, such as, for example, polyvinylcaprolactam, polyvinylpyrrolidone and their co-polymers, polyetherpolyol, associative thickeners, polyurea, sodium alginates, modified galactomannans, polyetherurea, polyurethane and nonionic cellulose ethers. As further additives, the inks according to the invention can be surface-active

Substances for the adjustment of surface tensions from 20 to 65 mN / m, which may be adjusted depending on the method used (thermal or piezo technology). Surfactants are, for example, surfactants of all kinds, preferably nonionic surfactants, butyldiglycol and 1,2-hexanediol.

Further, the inks may still contain conventional additives such as fungicidal and bacterial growth inhibiting agents in amounts of from 0.01 to 1% by weight based on the total weight of the ink.

The inks of the present invention can be prepared in a conventional manner by mixing the components in water.

Example 1 a) 8.0 g of the compound of the formula (IIIa) are added at room temperature to a mixture of 84 ml of acetic acid and 28 ml of propionic acid.

entered. After stirring for 5 minutes 5 ml of a 40% nitrosyl sulfuric acid is added dropwise at 0-5 ⁰ C and stirred at this temperature for two hours. The reacted mixture is slowly added at a temperature of 0-5 ⁰ C to a solution of 4.5 g of N, N-diethyl-m-toluidine in 39 ml of acetic acid and 13 ml of propionic acid and stirred for two hours. After raising the pH to 4.0 with sodium acetate, 314 ml of water are added and stirred for five hours. The resulting suspension is filtered off with suction, rinsed with water and dried. 10.9 g of the compound of the formula (IIa) are obtained.

b) In a round-bottom flask, 7.0 g of the compound of the formula (IIa) are stirred in 70 ml of NMP. After the addition of 0.5 g of imidazole, 0.7 g of copper (l) cyanide, 1, 1 g of zinc cyanide and 1, 3 g of sodium iodide is stirred at 70 ⁰ C for 1.5 h. After cooling, a solution of 2.9 g of iron (III) chloride in 150 ml of water is added dropwise and stirred for five hours. The suspension is filtered off with suction, rinsed with dilute hydrochloric acid and water and dried. This gives 6.2 g of the dye according to the invention of the formula (Ic)

the polyester colors in a slightly reddish blue tone.

Further dyestuffs according to the invention which can be prepared by the above process are given in Table 1. Table 1

Example 30

One part by weight of the dye of the formula (Ic) is mixed with 17 parts of water and two

Milled parts of a commercial dispersant in a bead mill and then converted into a 3% dispersion.

With this dispersion, after the high-temperature exhaust process at 130 ⁰ C, a 1% dyeing on polyester fabric created and cleaned with sodium dithionite reductive. The dyeing thus obtained has a very high wash fastness.

Example 31

A fabric consisting of polyester is made with a liquor consisting of 50 g / l of an 8% sodium alginate solution, 100 g / l of an 8-12%

Kernmehretherlösung and 5g / l monosodium phosphate padded in water and then dried. The fleet intake is 70%.

On the fabric thus pretreated, an aqueous ink prepared by the above-described procedure, containing

3.5% of the dye of the formula (Ia),

2.5% dispersing agent Disperbyk 190,

30% 1, 5-pentanediol,

5% diethylene glycol monomethyl ether,

0.01% biocide Mergal K9N and

58.99% water printed with a drop-on-demand (piezo) inkjet print head. The print is completely dried. The fixation takes place by means of superheated steam at 175 ⁰ C. during 7 minutes. Subsequently, the pressure is subjected to an alkaline reductive aftertreatment, rinsed warm and then dried.

Claims

claims

1. Dye of the general formula (I)

wherein

X ¹ and X ^{2 are} both hydrogen or both cyan;

R ¹ is ethyl, straight-chain or branched (C ₃ -C _O) -alkyl or - (CH ₂₎ _n COOR ^6;

R ^{2 is} hydrogen, methyl, cyanomethyl, halomethyl, ethyl, cyanoethyl,

Haloethyl, halo, -NH-CO-R ⁷ or -NH-SO ₂ -R ⁷ ; R ³ (C _r C ₈ ) -alkyl or by hydroxy, (dC ₄ ) -alkoxy, cyano, halogen,

-OCOR ⁷ , COOR ⁷ , vinyl or phenyl substituted (C _r C ₈ ) alkyl; R ^{4 is} hydrogen, (C 1 -C ₈ ) -alkyl or by hydroxyl, (C 1 -C ₄ ) -alkoxy, cyano,

Halogen, -OCOR ⁷ , COOR ⁷ , vinyl or phenyl substituted (C _r C ₈ ) -alkyl; R ^{5 is} hydrogen, halogen, (C _r C ₄ ) alkyl, (C _r C ₈ ) alkoxy or by halogen, cyano or phenyl substituted (dC ₈ ) alkoxy;

R ^{6 is} (C _r C ₄ ) alkyl;

R ^{7 is} (C 1 -C ₈ ) -alkyl or (C 1 -C ₈ ) -alkyl substituted by halogen or cyano; and n is 1, 2, 3, 4 or 5; mean, where

the compound in which R ^{1 is} - (CH ₂ ) _n COOR ⁶ with n = 2 and R ⁶ = C _r alkyl, X ¹ and X ^{2 are} both hydrogen, R ^{2 is} -NH-CO-R ⁷ with R ⁷ = C ₂ alkyl, one of the radicals R ³ and R ^{4 is} C ₂ - alkyl and the other by -OCOR ⁷ substituted C ₂ alkyl with R ⁷ = d-alkyl and R ^{5 is} hydrogen; Compounds in which R ^{1 is} branched C ₃ -alkyl, X ¹ and X ^{2 are} both hydrogen, R ^{2 is} -NH-CO-R ⁷ with R ⁷ = C ₃ -alkyl, the radicals R ³ and R ^{4 are} both C ₂ - Alkyl and R ^{5 are} hydrogen; and

Compounds in which R ^{1 is} isobutyl, X ¹ and X ^{2 are} both hydrogen, R ^{2 is} -NH-CO-R ⁷ where R ⁷ = C ₆ -alkyl or -NH-SO ₂ -R ⁷ where R ⁷ = C _r alkyl, the radicals R ³ and R ^{4 are} both C ₂ alkyl and R ^{5 is} hydrogen;

excluded are.

2. Dye according to claim 1, characterized in that R ^{5 is} hydrogen.

3. Dye according to claim 1 and / or 2, characterized in that it corresponds to the general formula (Ia)

wherein

R ^{1 is} n-pentyl or - (CH ₂ ) _n COOR ⁶ ; R ^{2 is} methyl, -NH-CO-methyl or -NH-SO ₂ -methyl;

R ^{6 is} methyl, ethyl or butyl; and n is 1, 2 or 3; mean corresponds.

4. Dye according to claim 1 and / or 2, characterized in that it has the general formula (Ib) wherein

R ^{1 is} ethyl or - (CH ₂ ) _n COOR ⁶ ;

R ³ and R ^{4 are} independently ethyl, - (CH ₂ ) ₂ CN, - (CH ₂ ) ₂ OMe, - (CH ₂ ) ₂ OAc, or n-butyl;

R ^{6 is} methyl, ethyl or butyl; and n is 1, 2, 3 or 5; mean corresponds.

5. Dye according to claim 1 and / or 2, characterized in that it is of the general formula (Ic)

wherein

R ^{1 is} iso-propyl, iso-butyl, sec-butyl or tert-butyl; and

R ³ and R ^{4 are} independently ethyl, - (CH ₂ ) ₂ CN, - (CH ₂ ) ₂ OMe, - (CH ₂ ) ₂ OAc, or n-butyl; mean corresponds.

6. A process for the preparation of a dye of general formula (I) in which X ¹ and X ^{2 are} both cyano, according to one or more of claims 1 to 3 or 5, characterized in that a compound of the general formula

(II)

wherein R ¹ to R ⁵ are defined as defined in claim 1, cyanated.

7. A process for the preparation of a dye of general formula (I) in which X ¹ and X ^{2 are} both hydrogen, according to one or more of claims 1, 2 and 4, characterized in that a compound of general formula (VII )

wherein R ¹ is defined as defined in claim 1, diazotized and to a compound of general formula (IV)

wherein R ² to R ⁵ are defined as defined in claim 1, coupling.

8. Use of a dye of the general formula I according to claim 1 for dyeing and printing of hydrophobic materials.

Ink for digital textile printing according to the ink-jet method, characterized in that it contains a dye of the general formula (I) according to claim 1