US3679350A - Process for the dyeing of textile materials made from mixtures of polyester and cellulosic fibres - Google Patents

Abstract

PROCESS FOR THE SEMI-CONTINUOUS OR CONTINUOUS DYEING OF TEXTILE MATERIAL MADE FROM MIXTURES OF POLYESTER AND CELLULOSIC FIBRES, THE POLYESTER FIBRE PORTION OF WHICH HAVING BEEN PREDYED WITH DISPERSE DYESTUFFS, BY IMPREGNATING SAID TEXTILE MATERIAL WITH AN ALKALINE SOLUTION CONTAINING A COUPLING COMPONENT AND A DIAZOAMINO OR TETRAZOAMINO COMPOUND OR AN ANTI-DIAZOTATE, AS WELL AS WETTING AND DISPERSING AGENTS, AND SUBSEQUENTLY TREATING THE TEXTILE MATERIAL, WITHOUT INTERMEDIATE DRYING, WITH AN ACIDIC SOLUTION AT TEMPERATURES OF FROM 50* TO 80*C. TO ACHIEVE DEVELOPMENT OF THE DYESTUFF OF THE FIBRE.

Description

PROCESS .FOR THE 3,679,350 Patented July 25, 1972 U States Patent Oflice DYEING F TEXTILE MATE- 'RIALS MADE FROM MIXTURES 0F POLYESTER AND CELLULOSIC FIBRES Rudolf Lowenfeld, Buchschlag, and Hans Kaiser, Offenbach am Main, Germany, assignors to Farbwerke Hoechst Aktiengesellschaft vormals Meister Lucius & Bruning, Frankfurt am Main, Germany No Drawing. Filed May 6, 1970, Ser. No. 35,301

Claims priority, application Germany, May 14, 1969,

P 19 24 803.4 Int. Cl. D06p 3/82 US. Cl. 8-21 C 6 Claims ABSTRACT on THE DISCLOSURE The present invention relates to a new process for the dyeing of textile material made from mixtures of polyester and cellulosic fibres.

It is known that textile material made from mixtures of polyester and cellulosic fibres can be dyed to yield fast shades by using disperse dyestufis and water-insoluble azo dyestuffs, the latter being produced on the fibre. The procedure is as follows: At first, 'the polyester fibre portion of the goods is dyed with disperse dyestuifs, either at boiling temperature and in the presence of dyeing accelerators, or under the conditions of the high-temperature dyeing method, or according to the Thermosol process; subsequently the water-insoluble azo dyestutf is produced on the cellulosic fibre portion by impregnation of the textiles with a coupling component and thereafter development of the dye with a diazotized aromatic amine. This process yields dyeings of good quality, but it needs much time and work, since the disperse dyestutf, the coupling component and the diazotized aromatic amine have to be applied in different dyeing baths.

A further well-known process is the following: The textile material is impregnated with an alkaline solution containing a coupling component, a diazoamino compound, a disperse dyestufi as well as a compound splitting ofi acids when heated. After drying the textiles, formation of the water-insoluble azo dyestuff on the cellulosic fibre portion is caused at temperatures of from 180 to 210 C., at the same time the disperse dyestuff is fixed on the polyester fibre portion, and finally, an alkaline after-treatment is carried out. This process is a very economic one, but its drawback resides in the fact that not all disperse dyestuffs are stable towards the high alkali quantities in the impregnation bath and that in an alkaline medium many disperse dyestuffs are not completely fixed on polyester fibres. On the other hand, also the development of the water-insoluble azo dyestulf is not complete under the conditions of dry heat fixation, so that the colour yield is insuflicient and the dyeings show considerably duller shades in comparison to those achieved by the way of a wet development. Further, this process requires an addition of urea, which may cause trouble in industrial practice on account of its annoying smell during the treatment with dry heat.

It has now been found that the aforesaid drawbacks in the dyeing of textile material made from mixtures of polyester and cellulosic fibres can be eliminated by impregnating said textile material, the polyester portion of which having been predyed with disperse dyestuffs, with an alkaline solution containing a coupling component and a diazoamino or tetrazoamino compound or an anti-diazotate, as well as wetting or dispersing agents, and subsequently treating it, without intermediate drying, with an aqueous solution of an acidic agent at temperatures of from about 50 to C. in order to develop the azo dyestuif on the fibre.

The process of the invention is carried out as follows: The textile material, for example mixed fabrics made from polyester and cellulosic fibres, the polyester fibre portion of which having been dyed at first with a disperse dyestuif in known manner by impregnation, drying and subsequent heat fixation, is impregnated with an alkaline solution containing a coupling component and a diazoamino compound, a tetrazoamino compound or an anti-diazotate, as well as wetting or dispersing agents, then squeezed out and wound on a roller. The alkali content of the impregnation bath has to be kept at a level that keeps the coupling component from precipitation during the'impregnation operation which is carried out at temperatures of from 30 to 60 C. The textile material has to be squeezed off thoroughly after its impregnation in order to obtain a very low liquor pick-up of the mixed fabric. After winding up the squeezed goods and dwelling them at room temperature of a slightly elevated temperature for a short time to allow for absorption of the coupling component by the fibre, or after an air-passage of the goods .while guiding them over a roller system, the material is impregnated with an acidic solution and squeezed out again between rollers. This second squeezing has to be carried out with a roller pressure as low as possible, in order to secure that resulting from the difference between the first and second squeezing a maximum liquid volume is absorbed by the already wet material. The temperature of the acidic impregnation bath should be between 50 and 80 C., so that the splitting and coupling process is instantaneous. The content of the compound having an acidic reaction has to be kept at a level which ensures neutralization of the alkali applied to the textile material together with the coupling component in the alkaline impregnation process, as well as a pH value of from 3 to 7 of the material to be dyed. After the impregnation with the hot acidic solution, the textile material is rinsed hot or cold and finally washed with alkaline baths, rinsed again and dried.

In the process of the invention, the water-insoluble azo dyestutf is produced on the cellulosic fibre portion giving high colour yields and clear shades. The dyeings obtained have very good fastness properties.

Examples of the textile material to be dyed are mixtures containing between 25% of polyester and 75% of cellulosic fibres, and 70% of polyester and 30% of cellulosic fibres.

Suitable polyester fibres in the blend are fibres made from aromatic polyesters, for example from terephthalic acid or diphenyl-4,4dicarboxylic acid and alkane diols or 1,4-cyclohexane-di-methanol, as well as consisting of triacetyl cellulose. The cellulosic fibre portion may be of natural orregenerated origin.

Examples of the coupling components to 1 be used in the process of the invention are especially aromatic o- 'hydroxy-carboxylic acid arylamides or acylaceticacid arylamides, 'for example 2,3-hydroxynaphthoic acid arylamides, 6-broffi'oor 6-alkoxy-2,3-hydroxynaphthoic acid arylamides or acetoacetic acid 'arylamides, which'have a low to "medium substantivity towards cellulosic fibres. When a suitable impregnationequipment is used, for example a small bath tank, also coupling components having substantivity towards cellulosic fibres may be used,

the condensation products from 2,3-hydroxy- -:haphthoic acid and polynuclear, isocyclic and heterocyclic amine slsuch asaminonaphthalenes, aminocarbazols or :aminodipihenylerieoirides, further heterocyclic o-hydroxycarboxylic acid -.arylamides, for example S.-- hydroxyboxylic acid amides, aminophenyl-alkylsulfones, aminophenyl--- arylsulfones or aminophenyl-aralkylsulfones,

" aminodiphenyl ethers,

trifiuoromethylanilines, monoa'cylated phenylenediamines, aminoazobenzenes or 4,4-

dia'minodiphenyls, and primary or secondary aliphatic or aromatic amines, for example N-alkylated aliphatic aminocarboxylic acids or aminosulfonic acids, N-alkylated aromatic aminocarboxylic acids, aminosulfonic acids, aminosulfocarboxylic acids or cyanamide.

As anti-diazotates there may be used those compounds which are obtainable from the above-mentioned primary aromatic amines. I

Q Suitable wetting or dispersing agents in the. alkaline impregnation bath are condensation products from highmolecular fatty acids and protein degradation products, condensation products from high-molecular fatty acids and aminoalkyl-sulfonie acids as well as purified sulfitecellulose waste liquor.

The compounds having an acidic reaction used in the acid developing bath maybe organic acids, such as formic acid, acetic acid, propionic acid, lactic acid, glycolic acid,

tartaric acid or citric acid, or salts having an acidic reaction, such as monosodium phosphate. The acidic developing bath contains also an additional quantity of the sodium salt of the corresponding acid used, so that the pH value can be maintained in a range of from 4 m6. As disperse dyestufi's for the pre-dyeing of. the polyester fibre portion there may be used such dyestuffs which are suitable for the Thermosol process on account of their thermic properties, i.e. dyestuffs which are capable of dyeing polyester fibresflat temperatures of from 170 to 210 C. and which do not soil the dyeing equipment on account of high volatility. Suitable disperse dyestuffs of this kind from the azo and anthraquinone series are described in Colour Index, Second Edition 1956, vol. 1, pages 1659-1742 and Supplement 1963, pp. S 179-224, as well as in the corresponding additions and amendments, No. 1 (September 1963) to No. 22 (January 1969). When the polyester fibre portion of the mixed fabric is dyed under the conditions of the high-temperature dyeing method (115- 125 C.) or at the boil in a long bath using carriers, also such disperse dyestuffs may be used which have no thermic stability at temperatures of from 170 to 210 C. Suitable disperse dyestuffs for the dyeing of polyester fibres at a temperature of from 100 C. to 125 C. are also described in Colour Index, Second Edition, 1956. H

The following example illustrates the invention:

Example A mixed fabric made from 67% of'polyethylene glycol I terephthalate fibres and 33% 'of cotton is impregnated with a solution containing, per litre of water of 30 C., '20 g. of Disperse Red 90, and is subsequently squeezed olf in such a way. that-the. liquor pick-up amounts to 70% of the dry weight of the goods. Thereafter, the fabric is dried at a temperature of about 100 C., and subsequently passed through a fixation chamberor over hot rollers, so that it is heated for 60 seconds to 180 210 C. The mixed fabric so pre-dyed is then impregnated at 40-60" C. with a solution containing, per litre of water,

4 g. of purified sulfite-cellulose waste liquor, 2 g. of a condensation product of oleic acid and methyl taurine, I

thediazoamino compound obtained from 8.4 g. of diazotized 1 amino 2 methyl 5 chlorobenzene and sodium cyanamide, 10 ml. of a 32.5% aqueous sodium hydroxide solution as well as 20 g. of 1 (2',3' hydroxy naphthoylamino) 2 methoxy 5 chlorobenzene, dis- ,solved in 50 ml. of denaturized alcohol, 10 ml. of a 'taining, per litre of water of C.,- ml. of a 50% acetic acid, 10 g. of sodium acetate and 50 g. of sodium chloride, and issubsequently squeezed between rollers so that the final liquor pick-up of the goods amounts to 100% of their dry weight. After an air-passage of about 1 minute, the fabric is first passed through a water bath of 60 C., then after-treated at 60 C. and at C. in a further bath containing 1 g. of a reaction product of 10 mols of ethylene oxide with 1 mol of nonylphenol, and 3 g. of sodium carbonate, per litre of water; thereupon it is rinsed and dried. The aftertreatment of the .dyed fabric may be also carried out in a bath containing with 2 g. of a 25% solution of the sodium salt of nitrilotriacetic acid, per litre of water. An intense red dyeing having good fastness properties is obtained.

The following table lists further coupling components and diazoamino compounds or anti-diazotates that may beused according to the process of the invention, and

. also disperse dyestuffs for the pre-dyeing of the polyester fibre portion, as well as the shades obtainable therefrom on mixed fabrics made from 67% of polyethylene glycol terephthalate fibres and 33% of cotton:

sufi'icient to absorb and level the coupling component on the fibre. 1

Diazoamino compound (DA) or Disperse dyestufl Coupling component anti-diazotate (AN) Shade 0.1. Disperse Red 82 1-(2,3-hydroxynaphthoylamino)-2- DA from diazotized 1-amino-2-methoxy-5- Bluish red.

methoxybenzene. chlorobenzene and sodium N-methylamino acetate. 0.1. Drsperse Orange 42 1-(2',3-hydroxyuaphthoylam1no)-2- DA from diazotized l-amino-2-methyl-3- Yellowish methylbenzene. chlorobenzene and sodium cyanamide. red. 0.1. Disperse Yellow 64 4,4'-bis-aeetoaeetylamino-3,3-dimethyl- DA from diazotized l-amino-2-methyl-5- Yellow.

diphenyl. chlorobenzene and sodium N-methylamino acetate. 0.1. Disperse Blue 79 1-(2,3-hydroxynaphthoylamino)-2-methyl- DA from diazotized 4,4-diamino-3,3- Blue.

4-ehlorobenzene. gimethoxy-diphenyl and N-methylaurme. Do- 2-(2,3-hydroxynaphthoylamino)- DA from diazotized l-anuno-2,5-diethoxy- Do.

naphthalene. 4-benzoylaminobenzene and sodium N methylamino acetate. 0.1. Disperse Yellow 64 and 0.1. Disperse 1-(2'-hydroxyanthracene-3-earboylamin0)- do Green.

Blue 35. 2-methylbenzene. 0.1. Disperse Red 82 and 0.1. Disperse 1-(2,3'-hydroxynaphthoylamino)-2,4- DA from diazotized l-amino-2-methyl-3- Dull bluish Orange 13. dimethoxy-fi-chlorobenzene. chlorobenzene and sodium cyauamide. red. 0.1. Disperse Red 82 1-(2',3-l1ydr0xynaphthoylamino)-2- AN from diazotized 1-amino-2-methoxy-5- Bluish red.

methoxyi-chloro-b-methylbenzeue. ehlorobenzeue. 0.1. Disperse Orange 42 1-(2',3-hydroxynaphthoylamino)-2- AN from diazotized 1-amino-2-ch1oro-5- Yellowish methoxybenzene. trifluoro-methylbenzeue. re 0.1. Disperse Orange 13 and 0.1. Disperse 1-(2-hydroxyearbazol-3-czrboylamino)-4- DA from diazotized l-amino-2-methyl-5- Brown.

Blue 56 and 0.1. Disperse Red 82. chlorobenzene. ehlorobenzene and sodium cyanamide. 0.1. Disperse Blue 81 and 0.1. Disperse 1-(5'-hydroxy-l ,2 ,1 ,2 -benzoearbazol-4' DA from diazotized l-amino-2-methoxy-4- Black.

Orange 13 and 0.1. Disperse Red 82. carboylamino)-4-methoxybenzene. nitrobenzene and sodium eyanamide. 0.1. Disperse Yellow 5 (0.1. 12 790)- 4,4'-bis-acetoacetylamino-83-dimethyl- DA from 1-amino-2-methyI-S-ehlorobenzene Yellow.

diphenyl. and sodium cyanamide. 0.1. Disperse Orange 1 (0.1. 11 080) 1-(2,3'-hydroxynaphthoylamino)-2-methoxy- AN from diazotized 1-amino-2-ehloro-5- Yellowish benzene. trifluorometliylhenzene. re 0.1. Dlsperse Red 17 (0.1. 11 210) 2,3-hydroxynaphthoylaminobenzene DA from diazotizecl l-amino-2-methyl-5- Red.

ehloro-benzene and sodium cyanamide. 0.1. Disperse Blue 9 (0.1. 61 115) .-do DA from diazotized l-amino-2-diethoxy- Blue.

4-benzoylaminobenzene and sodium N methylaminoacetate.

We claim:

1. In a process for the semi-continuous dyeing of textile material made from mixtures of polyester and cellulosic fibres wherein the polyester fibre portion has been predyed with disperse dyestuffs by impregnating said textile material with an alkaline solution containing a substantive coupling component, a diazoamino or tetrazoamino compound or an anti-diazotate derived from a primary aromatic amine, and a wetting or dispersing agent, and subsequently developing the dyestuif on the fibre by hot acid treatment, the improvement which comprises treating the alkaline/impregnated textile material, without intermediate drying, with an aqueous solution containing the acidic developing agent at a temperature of from 50 to 80 C. and a pH value of from 3 to 7.

2. A process as claimed in claim 1, wherein the impregnation of the textile material with the alkaline solution is carried out giving a low liquor pick-up of the textile material.

3. A process as claimed in claim 1, wherein the impregnation of the textile material with the alkaline solution is carried out at a temperature of from to 60 C.

4. A process as claimed in claim 1, wherein after the alkaline impregation the textile material is exposed to an air passage or is wound up and dwelled moist for a time References Cited UNITED STATES PATENTS 3,516,780 6/1970 Kirst et a1. 8-44 2,199,233 4/1940 Williams 8159 FOREIGN PATENTS 413,257 10/1932 Great Britain 8-44 OTHER REFERENCES Wygand, Am. Dye. Rep., December 1964, pp. 106-109. DuPont, Dyes and Chem. Tech. BulL, vol. 19, No. 2, October 1963, pp. 103-106.

GEORGE F. LESMES, Primary Examiner P. C. IVES, Assistant Examiner US. 01. X.R. s 44