US3708257A - Process for the dyeing of textile material made from mixtures of polyester and cellulosic fibers - Google Patents

Abstract

PROCESS FOR THE DYEING OF TEXTILE MATERIAL CONSISTING OF MIXTURES OF POLYESTER AND CELLULOSE FIBERS, WHEREIN SAID TEXTILE MATERIAL IMPREGINATED WITH AN ALKALINE SOLUTION CONTAINING A SUBSTANTIALLY COUPLING COMPONENT, AS WELL AS A WETTING OR DISPERSING AGENT, DRIED, SUBSEQUENTLY TREATED WITH AN ACID AQUEOUS SOLUTION CONTAINING A DIAZOTIZED AROMATIC AMINE AND A COMPOUND HAVING AN ACIDIC REACTION, FRIED, IMPREGNATED WITH AT LEAST ONE DISPERSE DYESTUFF AND THEN SUBJECTED TO A HEAT-TREATMENT.

Description

United States Patent U.S. Cl. 821 C 6 Claims ABSTRACT OF THE DISCLOSURE Process for the dyeing of textile material consisting of mixtures of polyester and cellulosic fibers, wherein said textile material is impregnated with an alkaline solution containing a substantive coupling component, as well as a wetting or dispersing agent, dried, subsequently treated with an acid aqueous solution containing a diazotized aromatic amine and a compound having an acidic reaction, dried, impregnated with at least one disperse dyestuff and then subjected to a heat-treatment.

It is known that textile material made from mixtures of polyester and cellulosic fibers can be dyed fast shades by using disperse dyestuffs and water-insoluble azo dyestuffs, the latter being'produced on the fiber. The procedure is as follows: 'the polyester fiber portion of the goods is first dyed with disperse dyestuifs, either at boiling temperature in the presence of dyeing accelerators, or under the conditions of high-temperature dyeing, or according to the so-called Thermosol process; subsequently the water-insoluble azo dyestufr is produced on the cellulosic fiber portion by impregnating the textiles with a coupling component and thereafter developing the dye with a diazotized aromatic amine.

In many cases, this process yields dyeings of useful quality. In other cases, especially with the production of blue, water-insoluble azo dyestuffs on the cellulosic fiber portion of the mixed fabrics, dyeings result the fastness of which to rubbing does not comply with the practical requirements.

The cause of the deficient fastness to rubbing may be seen in the fact that during development a certain portion of the water-insoluble azo dyestuif is formed in the surface zone of the polyester fiber portion and is not removed during the following washing process. This dyestutf which sticks to the polyester fiber portion is rubbed off on abrasion of the dyed fabric by means of undyed material and renders the dyeing substantially useless.

This invention is based on the observation that the aforesaid disadvantages in the dyeing of textile material made from mixtures of polyester and cellulosic fibers can be overcome by impregnating said textile material with alkaline solutions containing a coupling component as well as wetting or dispersing agents, drying and subsequently treating the material with aqueous solutions of acidic agents which contain a diazotized aromatic amine and a compound having an acidic reaction, drying, impregnating with at least one disperse dyestutf and then subjecting it to a heat-treatment.

The process of the invention is carried out as follows: the textile material, for example mixed fabrics made from polyester and cellulosic fibers, is impregnated with an alkaline solution containing a coupling component, as well as wetting or dispersing agents, squeezed and then dried. Thereby, the alkali concentration of the impreg nation bath should be kept at such a high level which ensures non-precipitation of the coupling component during impregnation. Subsequently, the textile material is impregnated with a solution containing compounds having an acidic reaction, a diazotized primary aromatic amine, as Well as, if desired or required, a dispersing agent. The concentration of the compounds having an acidic reaction should be at a level which ensures neutralization of the alkali applied to the textile material together with the coupling component in the alkaline impregnation process, and the material to be dyed should have a pH-value of from 4 to 7. Corresponding to the coupling capability of the diazotized aromatic amine used, the goods are subsequently treated in a neutral or alkaline cold or warm bath in order to complete coupling.

After dyestuff formation, the material is subjected to an alkaline after-treatment in usual manner at boiling temperatures, rinsed and dried. Subsequently, it is impregnated with the aqueous suspension of at least one disperse dyestuif, squeezed, dried and the textile material is subjected to a heat-treatment in the range of from about 170 to 220 C. This heat-treatment may be carried out by means of hot air or contact heat. In the process of the invention, remainders of the insoluble azo dyestufi, which had not been washed out before, and the disperse dyestuff applied at last, migrate into the interior of the polyester fiber during the heat treatment and are there fixed. Finally, the material is subjected to an alkaline after-treatment, rinsed and dried.

On this method, the azo dyestuif is obtained in full yield and clearness. The dyeingsobtained have a better fastness to rubbing than dyeings .with which first the disperse dyestutf was fixed separately by heat-treatment on the polyester fiber portion and the water-insoluble azo dyestutf was subsequently produced on the cellulosic fiber portion in known manner.

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

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

Examples of the coupling components to be used in the process of the invention are especially aromatic ohydroxycarboxylic acid arylamides or acylacetic acid arylamides, 6-bromoor 6-alkoxy-2,3-hydroxynaphthoic acid arylamides or acetoacetic acid arylamides which have a low to medium substantivity towards cellulosic fibers. When suitable impregnation equipment is used, for example one with a small-sized bath tank, coupling components having a high substantivity towards cellulosic fibers may also be used, for example the condensation products from 2,3-hydroxynaphthoic acid and polynuclear, isocyclic and heterocyclic amines, for example aminonaphthalenes, aminocarbazoles or aminodiphenyleneoxides.

As diazotized primary aromatic amines monoor diamines may be used, for example diazotized chloroanilines, dichloroanilines, chlorotoluidines, chloroanisidines, nitranilines, nitrotoluidenes, nitroanisidines, nitroxylidines, nitrophenetidines, cyanotoluidines, cyanoanisidines, aminobenzene sulfonic acid amides, aminobenzene carboxylic acid amides, aminophenyl-alkylsulfones, aminophenyl-arylsulfones or aminophenyl-aralkylsulfones, aminodiphenyl ethers, trifiuoromethylanilines, monoacylated phenylenediamines, aminoazobenzenes, as well as tetrazo- 4,4'-diamino-diphenyls.

3 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 4 passed into water of the temperature of 60 C., subsequently subjected to alkaline washing and dried. The material was then impregnated 'by means of an aqueous suspension of 40 g. of the disperse dyestuif: aniline 1-(2',3'-

and aminoalkyl sulfonic acids, condensation products 5 hydroxynaphthoylamino)-4-methoxybenzene per liter of from formaldehyde and naphthalene sulfonic acids, Monwater, squeezed in such a way that the liquor uptake opol brilliant oil as well as purified sulfite-cellulose amounted to 60% of the dry weight of the material, dried waste liquor. and passed through a fixing chamber or over hot rollers The compounds having an acidic reaction may be orin such a way that the goods were heated for 30-60 secganic acids, for example acetic acid, formic acid, propionds to 1-80" C.-210 C. onic acid, glycolic acid, tartaric acid or citric acid, com- Finally, the fabric was after-treated, at boihng templex chromium salts of the acetic acid which have weakly perature, with a solution containing 2 g. of a 30% reacidic reaction or other salts having an acidic reaction, action product of about 10 mols of ethylene oxide with for example monosodium phosphate or aluminium 1 mol of nonylphenol, 2 ml. of a 25% solution of the sulf t sodium salt of nitrilotriacetic acid and 2 g. of sodium As disperse dyestuffs there may be used such dyestuffs carbonate per liter of water and then rinsed hot and which are suitable for the Thermosol process on account cold- The after-treatment 0f the y fahl'lc might also o of their thermal propertles, 1.e. dyestufis which are capabe calmed out at 60 95 111 a bath Contalhlhg, ble of dyeing polyester fibers at temperatures in the range Per hter of water 3 a mlxture of 63% Perchlom' of from 170 to 220 C. and which do not soil the dyeii f g gig ing equipment on account of high volatility. Suitable dis- 2 g fi g 'gi g perse dyestuffs of the azo and anthraquinone series are p g 0 described in colouplndex second edition 1959 vol 1 of the SOdllllIl salt of mtrilo-triacetic acid. An intense red 1659 1742 d S 1 1963 S dyeing having good fastness properties was obtained. 1 T h an d as 25 The following table lists further coupling components, We 1 as t e correspon mg addmons and amen ments diazo components and disperse dyestuffs that may be used 1 (September 23 P according to the process of the invention, as well as the The Process of the lhvehtloh y t: earned out 6011- shades obtainable therefrom on mixed fabrics containing tinuously or sem1-cont1nuously. 67% of polyethylene terephthalate fibers and 33% of The following example illustrates the invention. cotton.

Coupling component Diazo component Disperse dyestufi Shade 1-(2',3 -hydroxynaphthoylamino)-2- l-arnino-3-chlorobenzenel-amino4-phenylazonaphthalenephenol Orange.

methoxybenzene. 2,3-hydroxynaphthoylaminobenzene. l-amlno-2-nitro-4-ehlorobenzene.. l-amino-4-nitrobenzener3-methy1-N,N-bis-B- Red.

hydroxyethylaniline. Do 1-amino-4-chloro-2-tnfiuorornethyl- Aniline 1-2,3-(hydroxynaphthoylamino)-4- Yellowish benzene. methoxybenzene plus 1-amino-4-nitrobenzene- 3- red.

methyl-N ,N-bis-B-hydroxyethylaniline. Do 1-amino-2-methoxy-4-mtrobenzene 1-amino-2cyano-4-nitrobenzene N,N-bls-(fl- Bluish red.-

acetoxyethyD-aniline. Do o-aminoazotoluene do Scarlet. 1-(2,3-hydroxynaphthoylaznino)- l-amino-2-methyl-fi-chlorobenzene- 1-amino-2-cyano-4-nitrobenzene- N-fl-eyanoethyl-N- Red.

Zagethoxybenzene. d B-carbomethoxyethylaniline. R d

0 0 O B l-acetoacetyl amino-2,5-dimethoxy-4- 1-a1nino-2-methyl-4-ehlorobenzene-. 1-amino-3-nitrobenzene 4-hydroxy-l-methylcarho- Yellow.

chlorobenzene. styryl.

Do l-amino-lchlorobenzene do Do. 4,4 -his-acetoacetylamino-3,3- do do Do.

dimethyl-diphenyl. 1-(2,3-l1ydroxynaphthoylamino)-Z- 1-a1nino-2-methyl-5-chlorobenzene l-amino-2-cyano-4-nitrobenzene- N-B-cyanoethyl-N- Red.

methyl-4-chlorobenzene. I B-carbomethoxyethylaniline. 2,8-hydroxynaphthoylaminobenzene.. 4-amino-4-methoxydrphenylamine-. 1,5-dihydroxy-4,8-diamino-bromoanthraquinone Blue.

Do 4-amino-2,5-din1ethoxy-2,6- l-amino-2-bromo-4,6-dinitrobenzene- 2-ethoxy-5- Navy blue.

dichloro-4-n1tro-1,l-azobenzene. acetylamino-N,N'bis-(fi-aeetoxyethyl)-an.iline plus lamino-3-nitrobenzene- 4-hydroxy-l-methylcarbostyryl plus 1-amino-2-cyano-4-nitrobenzene N-B- cyanoethyl-N-fl-carbomethoxyethylaniline. 1-(2,3-hydroxynaphthoylamino)-2, do 1-amino-2-bromo-4,G-dinitro-benzene 2'ethoxy-5- Do.

4-dimethoxy-5-ch1orobenzene. acetylamino-N N-bis-(B-acetoxyethyl)-aniline plus 1-amino-3-nitro enzene- 4-hydroxy-l-methylcarbostyryl plus l-amino-Z-cyano-4nitrobenzene- N-B- eyanoethyl-N-B-carbomethoxyethylaniline. 2,3-hydroxynaphthoylaminobenzene. 1-ammo-4-benzoylammo-2,5- 1,8-dihydroxy-4,5-diaminoanthraquinone Blue.

diethoxy-benzene.

EXAMPLE A mixed fabric .consisting of 67% of polyethylene terephthalate fibers and 33% of cotton was impregnated with a solution containing per liter of water 14 g. of 2,3- hydroxynaphthoylaminobenzene dissolved in 14 ml. of 32.5% sodium hydroxide solution and water of the temperature of 90 C., as well as 4 g. of a Wetting agent of the type of the oleic sulfonates. The fabric was then squeezed in such a way that the liquor uptake amounted to 60% of the dry weight of the material, dried and impregnated wtih a solution containing per liter of water 7.6 g. of diazotized 1-amino-2-nitrobenzene, 20 ml. of acetic acid and 15 g. of sodium acetate, and once more squeezed in such a way that the liquor uptake amounted to of the dry weight of the material. After an air passage of about 60 seconds, the goods were What we claim is:

1. A process for the dyeing of textile material consisting of mixtures of polyester and cellulosic fibers, wherein said textile material is impregnated with an alkaline solution containing a substantive coupling component, as well as a wetting or dispersing agent, dried, subsequently treated with an acid aqueous solution containing a diazotized aromatic amine and a compound having an acidic reaction, dried, impregnated with at least one disperse dyestufi and then subjected to a heat-treatment.

2. A process as claimed in claim 1, wherein the coupling component is an aromatic or heterocyclic ohydroxycarboxylic acid arylamide or an acetoacetic acid arylamide.

3. A process as claimed in claim 1, wherein a dia zo OTHER REFERENCES compound of the benzene, drphenyl or azobenzene series Fortess et a1 Amen Dyestufi Report?r May 1963 pp is used. 402409.

A process as claimed in claim i a disperse Schmidlin, Preparation and Dyeing of Synthetic Fibers, dyestufi anthmqmime 5 Publ. April 1963 by Chapman & Hall Ltd pp 264274 5. A process as claimed in claim 1, wherein the acid W J W Amer D estufl Re fDecembel: impregnation is carried out at a pH in the range of from 1964' pi g y p 6. A process as claimed in claim 1, wherein the heat- DuPont Bulletin D438 March 1970 treatment is effected at a. temperature within the range 10 I I of from to C. GEORGE F. LESMES, Primary Examiner References Cited UNITED STATES PATENTS 3 26 46 3,416,873 12/1968 Fono et a1. 821 C 3,100,132 8/1963 Jenny et a1. 8-39 T. J. HERBERT, IR., Assistant Examiner US. Cl. X.R.