US3642424A - Process for dyeing textile material of mixtures of polyester and cellulose fibers - Google Patents

Abstract

Textile materials consisting of mixtures of polyester and cellulose fibers are dyed equal shades by (a) impregnation with an alkaline solution containing a coupling component, and wetting or dispersing agents, (b) drying the material, (c) impregnation with an acid solution containing a diazotized aromatic or heterocyclic amine and a disperse dye, (d) drying the material and (e) subjecting it to a heat treatment.

Description

United States Patent Lowenfeld et al.

[4 Feb. 15, 1972 PROCESS FOR DYEING TEXTILE MATERIAL OF MIXTURES OF POLYESTER AND CELLULOSE FIBERS lnventors: Rudolf Lowenfeld, Buchschlag; Uwe Kosubek, Offenbach/Main, both of Germany Assignee: Farbwerke Hoechst Aktiengesellschaft vormals Meister Lucius & Bruning, Frankfurt/Main, Germany Filed: July 7, 1969 Appl. No.2 839,647

Foreign Application Priority Data July 11, 1968 Germany ..P 17 69 775.5

Int. Cl. ..D06p 3/82 Field of Search ..8/2l

References Cited UNITED STATES PATENTS 12/1968 Fono et al. ..8/2l C OTHER PUBLICATIONS llg Mell. Text 111)., 2/1963, p. ]76|79, English Trans].

Ab J. Soc. Dyers & Colorists, 6/1963, 278 AM. D. Rep..

Wygand, 12-7-1964, p. 106-109 Primary ExaminerGeorge F. Lesmes Assistant Examiner-Patricia C. lves AtrorneyConnol1y and Hutz [5 7] ABSTRACT 5 Claims, No Drawings PROCESS FOR DYEING TEXTILE MATERIAL OF MIXTURES OF POLYESTER AND CELLULOSE FIBERS The present invention provides a process for dyeing textile material of mixtures of polyester and cellulose fibers.

lt is already known that textile material consisting of mixtures of polyester and cellulose fibers may be dyed fast shades, using disperse dyestuffs and water-insoluble azo dyestuffs produced on the fiber. The process is carried out in such a manner that the portion of polyester fiber is first dyed with disperse dyestuffs at boiling temperature, in the presence of dyeing accelerators, under the conditions of high-temperature dyeing or according to the so-called thermosol-process, and subsequently, the water-insoluble azo dyestuff is produced on the cellulose fiber portion by impregnation with a coupling component and subsequent development with a diazotized aromatic amine. When the process is carried out in this manner, dyeings of good quality are obtained. However, it takes a long time as the disperse dyestuff, the coupling component and the diazotized aromatic amine must each be applied in separate dyeing baths.

it has now been found that it is possible to avoid this disadvantage in the process of dyeing textile material of mixtures of polyester and cellulose fibers, by treating the textile material with alkaline solutions containing a coupling component as well as wetting or dispersing agents, drying it, subsequently treating with acid solution containing, in addition to compounds giving an acid reaction, a diazotized aromatic or heterocyclic amine as well as at least one disperse dyestuff, drying and then subjecting it to a heat treatment.

According to the process of the invention the textile material, for example blended fabrics of polyester and cellulose fibers, is impregnated with an alkaline solution containing a coupling component as well as wetting or dispersing agents, and it is then squeezed off and dried. During the process, the content of alkali in the impregnation bath must be such that the coupling component does not precipitate. Depending on the nature and the concentration of the coupling component, 5 to 30 ml. of a 32.5 percent sodium hydroxide solution per liter of water are used as alkali. Subsequently, the textile material is impregnated with a solution containing a compound giving an acid reaction, a diazotized primary aromatic or heterocyclic amine as well as a disperse dyestuff. The content of the compound giving an acid reaction must be such that the alkali applied onto the textile material together with the coupling component in the course of the alkaline impregnation is neutralized, and that the pH-value of the goods to be dyed still is between about 3 and 7. The disperse dyestuff is used in an amount such that the polyester fiber portion is dyed with approximately the same intensity as the cellulose fiber portion. After the impregnation with the acid developing bath containing the diazotized amine and the disperse dyestuff, the textile material is squeezed off, dried and subjected to a heat treatment at temperatures in the range offrom 170 to 210 C. This heat treatment may be carried out with hot air or contact heat. Finally, the material is washed in an alkaline solution, rinsed and dried.

In the process of the invention, the water-insoluble azo dyestuff develops on the cellulose fiber portion when the material impregnated with the coupling component is brought into the acid developing bath. The disperse dyestufi is applied onto the material during the coupling at its passage through the developing bath, but it is only fixed in a fast manner on the polyester fiber portion in the course of the heat treatment at temperatures in the range of from 1707 to 210 C. Thereby, the water-insoluble azo dyestuff is obtained in full yield and clearness. The dyeings obtained possess very good fastness properties.

As textile materials, there maybe used blends containing from about percent of polyester'fiber and 75 percent of cellulose fiber to 70 percent of polyester'fiber and percent of cellulose fiber.

Appropriate polyesterfibers are those made of aromatic 'po'lyesters,'for example of =terephthalic acid or diphenyl-4,4'-

dicarboxylic acid and alkane diols or l,4-cyclohexanedimethanol, as well as triacetyl cellulose. As cellulose fibers, native or regenerated cellulose fibers may be used.

In the process of the invention, the coupling components which 1 enter into consideration are especially aromatic ohydroxy-carboxylic acid arylamides or acylacetic acid aryla mides, such as, for example, 2,3-hydroxynaphthoic acid arylamides, 6-bromo or 6-alkoxy-2,3-hydroxynaphthoic acid arylamides or acetoacetic arylamides whose substantivity with respect to cellulose fibers is weak to medium. When appropriate impregnation equipments are used, having for example a small liquor reservoir, it is also possible to use coupling components which have a high substantivity with respect to cellulose fibers, for instance the condensation products of 2,3- hydroxynaphthoic acids with polynuclear isocyclic or heterocyclic amines, such as aminonaphthalenes, aminocarbazoles or aminodiphenylene oxides, moreover heterocyclic ohydroxy-carboxylic acid arylamides, for example, S-hydroxyl,2,l',2-benzocarbazole-4-carboxylic acid arylamides, 2- hydroxycarbazole-3-carboxylic acid arylamides, and 4,4'-bis- (acetoacetylamino)-diphenyls or Z-hydroxy-anthracene-llcarboxylic acid arylamides.

As diazotized primary aromatic or heterocyclic amines there may be taken into consideration monoamines or diamines, for example diazotized chloro-anilines, dichloroanilines, chloro-toluidines, chloro-anisidines, nitroanilines, nitrotoluidines, nitroanisidines, nitroxylidines, nitrophenetidines, cyanotoluidines, cyanoanisidines, aminobenzene-sulfonic acid amides, aminobenzene-carboxylic acid amides, aminophenyl alkyl-, arylor -aralkyl-sulfones, aminodiphenyl ethers, trifluoro-methyl anilines, monoacylated phenylenediamines, arninoazobenzenes or aminocarbazoles as well as tetrazotized 4,4'-diamino-diphenyls.

As wetting or dispersing agents in the alkaline impregnation bath there may be used especially condensation products of high-molecular-weight fatty acids and protein degradation products, condensation products of high-molecular-weight fatty acids and aminoalkylsulfonic acids, condensation products of fonnaldehyde and naphthalene sulfonic acids as well as purified waste lignin liquor.

The compounds giving an acid reaction in the developing bath are either organic acids such as, for example, acetic acid, formic acid, propionic acid, lactic acid, glycolic acid, tartaric acid or citric acid, or salts giving an acid reaction such as, for example, monosodium phosphate or aluminum sulfate. When nonvolatile acid compounds are used, care must be taken that a quantity not higher than that required for the neutralization of the alkali applied onto the material is used. An excess amount of a nonvolatile acid compound might cause, during the subsequent heat treatment, a damage of the cellulose fiber portion of the fabric.

As disperse dyestuffs, there may be used dyestuffs which, due to their thermal properties, can be used in the so-called thermosol treatment, i.e., dyestuffs which dye polyester fibers at temperatures in the range of from to 210 C. and do not soil the coloring aggregates because of a high volatility. Suitable disperse dyestuffs of the azoand anthraquinone series are described in Color index Second Edition 1956, Vol. l, page 1659-1742 and Supplement I963, p. 8179-5224, and in the corresponding Additions and Amendments, No. 1, Sept. 1963 to No. l8,.lan. I968.

The process of the invention maybe carried out continuously or semicontinuously.

With-respect to the known methods of working in which, in the first operating stage, the disperse dyestuff is fixed on the polyester fiber portion of the blended fabric by a thermosol treatment, the process of the invention allows the application of the disperse dyestuff to be combined with the manufacture of the water-insoluble azodystuff on the cellulose fiber portion of the blended fabric. in this manner, one working stage can be omitted.

The following examples illustrate the inventionybut they are not intended to limit it thereto, the parts and percentages beingby weight.

EXAMPLE l acid per liter of water. A full red dyeing with good fastness A blended fabric consisting of 67 percent of a polyethylene Properties was obained' glycol terephthalate fiber and 33 percent of a cotton fiber was The following table indicates a series of further coupling impregnated with a solution containing, as per liter of water, components and diazo components to be used according to 16.6 g. of 2,3-hydroxynaphthoylaminobenzene dissolved in 5 the invention, as well as disperse dyestuffs and the shades obl6.6 ml. of sodium hydroxide solution (32.5 percent) and hot tainable therefrom on mixed fabrics of fibers of polyethylene water of 90 C., 4 g. of a condensation-product of formalglycol terephthalate (67 percent) and cotton (33 percent).

Coupling component Diazo component Disperse dyestufl Shade 2 3.] yd oxynaphthoylaminobenzcno 1'-amino-2-nitrel enzene 0.1. disperse orange 13.. Orange. 1-(2',3-hydroxynephthoylemino)-2phlorobenzene l-itmine-3,E-bis-trilluoromothylbonzene- 0.1. disperse yellow-68.- Golden yellow. 1-(2,3'-hydroxynaphthoylamino)-4-ehlorobenzene l-amino4-ehloro-iZ-triiluoromethylbenzene. 0.1. disperse red 82 Blueish red. 1- 2',3'-h drex ne htho iemino)-2-methylhenzene. l-amino-l-chlorobenzeue 0.1. disperse orange 13.. Orange. 1-(2,3'-hydroxynaphthoylamin0)-2-muth0xyb0t1zefl0. l-amino-B-ehlorobenzene do De, 1-(2,3'-hydroxynaphthoylamino)-2-methylbenzenel-emino-Z-methyl-fi-nitrobenzene. 0.1. disperse red 91 Red. 1-(2,3-hydroxynaphthoyiamino)-2-ethoxybenzene. 1-arnino-2,5-dlmethoxyt-benzo-nitrlle.. 0.1. disperse red 90 Bordo. v 1-(2',3-hydroxynaphthoylamino)-2-methylbenzene l-apiilinlo-rirgathoxybenzene-fi-sulionic acid di- C.I. disperse red 82 Blueish red.

1-(2',3-hydr0xynaphthoylarnino)-2-meth0Xybel'1Zen6.. 1-amino-2-methy1-5-chlorobenzene 0.1. disperse red 91 Red.

Do 0.1. disperse red 90 Red. 1-(2',3'-h dr0xynaphthoylamino)-2-methylbenzene o do 1-(2,3'-hydroxynaphthoylamino)-2-methyl-4-methoxyl-amino-2-methyl-4-ehlorobenzene de benzene. 1-(2',3-hydrexynaphtoylamine)-2,4-dimethoxy-5-chloro- 1-amine-2methexy-E-chlorobenzene do Blueish red.

benzene. 2 3.hydroxvnaphthoylaminobenzene 1-emino-4-bem.oylamine-2.5-diethoxybenzene. 0.1. disperse blue 81. Blue. 1-(2',3'-h droxynaphthoylemino)-2-methoxybenzene. 4,4-diamin0-3,3-dimethoxydipheny1 de Do, 2,3-hydroxynaphtoylaminobenzenc 4-amin0-4-mei:hoxydiphenylamine. do Do. 1-(2-liydroxyearbezol-3-earboylumino)-4-ohlorohenzcne. l-emino-Z-methyl-B-ehiorobenzene 0.1. disperse orange 13 Brown.

plus 0.1. disperse blue 66 plus 0.1. disperse red 82. 1-(3-iiydrexydiphenyleneoxide-W-cerboylamino)-2,5- ..-..do 0.1. disperse orange 13 Do.

dimetlioxybonzene. plus 0.1 disperse blue 56drgl2us 0.1. disperse re 1-(5-hydroxy-i,2,1,2"-benzocerbuzol-4 cerboylamin0)- 1-emin0-2-methoxy-4 mitrobenzene 0.I. disperse blue 81 Black.

4-metl1oxybenzene plus 0.1. disperse orange 13 lus 0.1.

disperse re 82. 4,4-bis-acetoacetylamino-S,3dimethyl-d1phenyl l-amino-Z-ehlorobenzene.... 0-I- disperse yellow 5 Yellow. Therephthlalloyl-his;(l-acetyl-aminoa-meth0Xy-4chl0r0- 1-amino-2,fidichlorobenzene C.I. disperse yellow e3 Do.

5-metl1y enzene e-methoxy-2.3-hydroxynaphthoylaminobenzene l-amin0-2-methyl-5-chiorobenzene 0.1. disperse red 82 Bordo.

dehyde with B-naphthalenesulfonic acid and 0.5 g. of sodium 4 We claim: 7 salt of 2,5-dibutylnaphthaline sulfonic acid. Subsequently the. 1. In a process for dyeing textile materials consisting of mixfabric wa squeezed off until th li uor ab o ti h d tures of polyester and cellulose fibers by impregnating the texreached 60 percent of the dry goods weight, dried and imtile material with an alkaline solution containing a coupling pregnated with a solution containing, per liter of water, 10.6 g. pf and Wemng f dlsperslllg drymg h of diazotized l-amino-2-methyl-chlorobenzene, 21 ml. of a 50 "l f q lfl f p g fi material percem acetic acid, 10 g. f Sodium acetate, 3 f Cl with an acid solution containing at least one disperse dyestuff Disperse Red 90, and 2 g. of a condensation product of formaldehyde with B-naphthalenesulfonic acid. Subsequently, the fabric was squeezed off until the liquor absorption had reached 60 percent of the dry goods weight and the fabric was I then passed through a drying aggregate to a fixation chamber .S 3 l e fl ffla e i 9ibii te y qe ivfi' or over hot rollers in a manner such that it was heated to to obtain a pH from about 3 to 7, drying the material and then subjecting this dried material to heat treatment ata temperature in the range of about 170 to 210 C., the improvement which consists essentially of adding in the acid impregnation 2. The process as claimed in claim 1 wherein the l80-2i0C. during 30 to 60 seconds. Finally, the fabric was component is an aromatic y yy acid y after-treated, at boiling temperature, with 2 g. of a 30 percentamide an acylaceto amidereaction product of about 10 moles of ethylene oxide and l mole of nonyl phenol and 2 ml. of a 25 percent solution of the sodium salt of nitrilotriacetoacetic acid per liter of water, and rinsed in hot and cold baths. The after-treatment of the dyeing could also be carried out, at temperatures in the range of from to 95 C., in a bath containing 3 g. of a mixture consisting of 63 percent of perchloroethylene, 17 percent of a reaction product of about 10 moles of ethylene oxide and 1 mole of nonyl phenol and 20 percent of isopropyl alcohol and 2 g. of a 25 percent solution of the sodium salt of nitrilotr iacet oacetic 65 compound is of the benzene, diphcnyl or carbazole series.

dye is of the azo or anthraquinone series.

acid or a purified waste lignin liquor.

3. The process as claimed in claim 1, wherein the diazo 4. The process as claimed in claim 1, wherein the disperse 5. The process as claimed in claim 1, wherein the wetting or 60 dispersing agent is a condensation product of a long-chain fatty acid and a protein degradation product or an aminoalkyl sulfonic acid or of formaldehyde and a naphthalene sulfonic

Claims (4)

1. 2. The process as claimed in claim 1, wherein the coupling component is an aromatic o-hydroxy-carboxylic acid aryl amide or an acylaceto aryl amide.
2. 3. The process as claimed in claim 1, wherein the diazo compound is of the benzene, diphenyl or carbazole series.
3. 4. The process as claimed in claim 1, wherein the disperse dye is of the azo or anthraquinone series.
4. 5. The process as claimed in claim 1, wherein the wetting or dispersing agent is a condensation product of a long-chain fatty acid and a protein degradation product or an aminoalkyl sulfonic acid or of formaldehyde and a naphthalene sulfonic acid or a purified waste lignin liquor.