US3764262A - Process for the dyeing and printing of textile materials - Google Patents

Process for the dyeing and printing of textile materials Download PDF

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US3764262A
US3764262A US00070514A US3764262DA US3764262A US 3764262 A US3764262 A US 3764262A US 00070514 A US00070514 A US 00070514A US 3764262D A US3764262D A US 3764262DA US 3764262 A US3764262 A US 3764262A
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parts
water
dyestuffs
formula
perchloroethylene
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D Hildebrand
H Kirschnek
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Bayer AG
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Bayer AG
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/90—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof
    • D06P1/92—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents
    • D06P1/922—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents hydrocarbons
    • D06P1/924—Halogenated hydrocarbons

Definitions

  • the invention relates to the dyeing and printing of textile materials with chlorinated hydrocarbon/ water dyestuff emulsions, the aqueous phase of which contains a solution of water-soluble dyestuffs and the chlorinated hydrocarbon phase of which may be a solution of dyestuffs soluble in chlorinated hydrocarbons, and to an after-treatment in chlorinated hydrocarbon solutions containing compounds which are interface-active in chlorinated hydrocarbons.
  • the invention relates to a process for the dyeing and printing of textile materials with chlorinated hydrocarbon/Water dyestuff emulsions; the process is characterised in that the textile materials are dyed or printed with chlorinated hydrocarbon/water dyestutf emulsions the aqueous phase of which is a solution of water-soluble dyestuffs and the chlorinated hydrocarbon phase of which may be a solution of dyestuffs soluble in chlorinated hydrocarbons; and that the materials are sub sequently, possibly after a heat treatment, subjected to an after-treatment in chlorinated hydrocarbon solutions containing compounds which are interface-active in chlorinated hydrocarbons and convert the dyestuffs used into a form soluble or dispersible in chlorinated hydrocarbons.
  • the compounds are expediently used in an amount of 0.02-2 percent by weight, referred to the weight of the chlorinated hydrocarbons.
  • the compounds which are used in the chlorinated hydrocarbon baths for after-treatment according to the invention, in order to convert the dyestuffs used into a form soluble or dispersible in chlorinated hydrocarbons, can be divided into two groups, on account of their behaviour towards the various dyestuffs.
  • Group (A) This group comprises the compounds which convert basic dyestuffs as Well as acidic dyestuffs, anionic metal complex dyestuffs which are free from sulpho groups, or reactive dyestuffs which contain sulpho groups, into a form soluble or dispersible in chlorinated hydrocarbons.
  • the compounds of this group are preferably used in the after-treatment baths of the process according to the invention.
  • Group (B) This group comprises the compounds which convert only basic dyestuffs into a form soluble or dispersible in chlorinated hydrocarbons.
  • the compounds belonging to group (A) are the following:
  • R stands for an alkyl, alkenyl or aralkyl radical which carries 12-18 carbon atoms and may be interrupted by hetero atoms such as oxygen, sulphur and/or nitrogen atoms;
  • R and R independently of one another, denote an alkyl, alkenyl or aralkyl radical which carries 1-28 carbon atoms and may be interrupted by hetero atoms such as oxygen, sulphur and/or nitrogen atoms; and may 'be substituted;
  • R means an optionally substituted C 'C -alkyl
  • R stands for hydrogen or R where R, has the same meaning as in Formula I, or together with R forms a 5- or 6-membered non-aromatic heterocycle, with the proviso that the sum total of the carbon atoms contained in R R and R amounts to at least 20 and at most 60.
  • R Suitable alkyl, alkenyl or aralkyl radicals which contain 12-28 carbon atoms and may be interrupted by hetero atoms such as oxygen, sulphur and/or nitrogen atoms are the following, for example:
  • C C -alkyl radicals such as the dodecyl, tetradecyl, hexadecyl, octadecyl, eicosyl, docosyl, 3,6,9-trirnethylhexadecyl, l-octyl-dodecyl and l-undecyl-dodecyl radicals;
  • Saturated radicals with a carbon chain interrupted by hetero atoms such as 3-oXa-nonadecyl-( 1), 3-oxa-heneicosyl-(l), 4-oxa-docosyl-(1), 3,6-dioxa-docosyl-(1), 3- thia-heneicosyl-(l), dodecyl aminoethyl, hexadecylaminopropyl, octadecyl-arninoethyl, octadecyl-aminopropyl, octadecyl-aminobutyl, eicosyl-aminopropyl, docosylaminopropyl radical and especially the dodecanoyl-amind ethyl, tetradecanoyl-aminoethyl, hexadecanoyl-aminobutyl, octadecanoyl-amin
  • C -c -alkenyl radicals such as the oleyl, linolyl, linolenyl, eicosenyl, docosenyl and 2-ethyl-octadecen-9,l0- yl-( 1)-radicals;
  • Unsaturated radicals with a carbon chain interrupted by hetero atoms such as 3-oxa-nonadecen-l0,ll-yl-(l), 4-oxadocosen 13,14-yl-(l), hexadecen-7,-8-yl-aminoethyl, octadecen 9,10 yl aminoethyl, docosen 13,14 ylaminopropyl and especially the oleoyl-aminoethyl, linoleuoyl-aminopropyl, linolenoyl aminoethyl, eicosenoylaminopentyl and docosenoyl-aminoethyl radicals;
  • Aralkyl radicals with a carbon chain interrupted by hetero atoms such as the (4-nonyl-phenyl)-ethyl-carboxyethyl radical.
  • R and R Suitable alkyl, alkenyl or aralkyl radicals which contain l28 carbon atoms and may be interrupted by hetero atoms and/or may be substituted, are the following, for example:
  • C -C -alkyl radicals such as the methyl, ethyl, isopropyl, dodecyl, hexadecyl, octadecyl, eicosyl and docosyl radicals;
  • C C -alkenyl radicals such as the buten-3,4-yl-(l)- and undecen-10,l1-yl-(l) radicals;
  • Substituted alkyl and alkenyl radicals such as the 2- hydroxyethyl, 3-hydroxypropyl, 3-hydroxybutyl, 13-hydroxy-octadecen-9,l-yl-(1), 2 chloroethyl, 3 chlor0 propyl, 1 l-bromoundecyl, 13-chloroctadecen-9,l0-yl-( l l3,l4 dichlorodocosyl, Z-cyanoethyl, 3-cyanopropyl, llcyano-undecyl, 3-aminopropyl, 3-(N-methyl-amino)-butyl, ll-amino-undecyl, l3-(N-methylamino)-docosyl and the carbethoxy-ethyl radicals;
  • Alkyl and alkenyl radicals with a carbon chain interrupted by hetero atoms such as the methoxy-ethyl, ethoxy-butyl, 3-oxa-dodecyl-(1), S-OXa-heneicosyl- 1 3,6-dioxa-docosyl-( l 4-thia-hexenyll 3-thia-pentadecyl-(l), N-methyl-Z-aminoethyl, N-ethyl 3 aminopropyl, N-propyl 3 aminopropyl, N-dodecyl-Z-aminoethyl, N octadecyl-B-aminopropyl, N-heneicosyl-4-aminobutyl and the N-docosyl-6-aminobutyl radicals;
  • Aralkyl radicals such as the bcnzyl, 4-chlorobenzyl, 3- methyl-benzyl and 4-nonylphenyl-ethyl-carboxyethyl radicals.
  • Suitable, optionally substituted C C -alkyl, C C -alkenyl, cycloalkyl or aralkyl radicals are the follow ing, for example:
  • C C -alkyl radicals such as the methyl, ethyl, isopropyl, sec.-butyl, Z-ethylhexyl, dodecyl, 2-hydroxyethyl, 3-hydroxy-propyl, Z-methoxyethyl, 2,3-epoxypropyl, chloromethyl, 2-bromoethyl, chloropropyl, 2-hydroxy-3-chlo ropropyl, 2,3-epoxy-propyl, carbethoxymethyl, carboxamidomethyl, Z-cyanoethyl, acetoxyethyl and S-trimethylammonium-propyl radicals.
  • C C -alkenyl radicals such as the buten-3,4-yl-(1)- undecen-l0,l1-yl-(1) radicals;
  • Cycloalkyl radicals such as the cyclohexyl, 4-methylcyclohexyl, 3-octylcyclohexyl and 4-chlor0cycl0hexyl radicals;
  • Aralkyl radicals such as the benzyl, 3-methylbenzyl, 4- cyclohexyl-benzyl, 4-methoxybenzyl and 3-chlorobenzyl radicals.
  • Suitable 5- or 6-membered heterocycles which may be formed by R together with R are primarily the morpholine and piperidine rings.
  • Suitable anions X- are anions of organic acids, such as the chloride, bromide, iodide and sulphate ions; the anions of acidic esters of inorganic acids, such as the methyl-sulphate, ethyl-sulphate and toluene-sulphate ions; and the anions of or organic acids, such as the acetate, propionate, ethyl-caproate, oleate, behenate, benzoate and salicylate ions.
  • organic acids such as the chloride, bromide, iodide and sulphate ions
  • the anions of acidic esters of inorganic acids such as the methyl-sulphate, ethyl-sulphate and toluene-sulphate ions
  • the anions of or organic acids such as the acetate, propionate, ethyl-caproate, oleate, behenate, benzoate and salicylate ions.
  • Suitable alkylene radicals which contain 1-8 carbon atoms and may be interrupted by hetero atoms are the following, for example:
  • Alkylene radicals such as 'the methylene, ethylene, propylene-1,2, propylene-1,3, butylene and hexylene radicals;
  • Alkylene radicals interrupted by hetero atoms such as the 3-oxa-hexylene-L6 and 3,6-dioxa-octylene-L8 radicals.
  • onium compounds of the Formula II are the following sulphonium compounds, for example:
  • quaternary ammonium compounds of the Formula 111 are the following, for example:
  • the compounds belonging to the group (B) are the following:
  • Sulphates of monoand polyhydric alcohols containing at least 16 carbon atoms such as cetylsulphate, stearyl sulphate, oleyl sulphate, behenyl sulphate, 2-heXyl-decanol-l-sulphate, 2,4,6-triethyl-decanol-l-sulphate, 3,10-diethyl-tridecanol-7-sulphate, 1,Z-diundecyl-ethylene-glycol monosulphate, glycerol-monostearate monosulphate;
  • sulphates obtainable by sulphonation of unsaturated fatty acids, fatty acid esters and fatty acid ester amides, such as oleic acid sulphate, oleic acid butyl ester sulphate, ricinoleic acid ethyl ester sulphate, oleic acid ethylamide sulphate, oleic acid ethanolamide sulphate, oleic acid diisobutylamide sulphate, oleic acid anilide sulphate,
  • cfia-O-C O(CH2) 10-0 -13 sulphates of acylated or alkylated polyglycol ethers containing not more than 30 ethylene oxide and/or propylene oxide units in the molecule, such as CH (CH CH CH(CH CONH (C2H4O)1BSO3NK polypropylene glycol ether monosulphate (mol.
  • acylated or alkylated alkanolamines such as N-acetyl-oleylamine sulphate Sulphates of monohydroxy-polycarboxylic acid esters, such as Acidic phosphoric acid esters, such as dioctadecyl phosphate and CH (CHa)mC ONHC2H4O-P
  • Acidic phosphoric acid esters such as dioctadecyl phosphate and CH (CHa)mC ONHC2H4O-P
  • Alkyl-sulphonic acids such as Araliphatic sulphonic acids, such as CH: CH:
  • Aromatic sulphonic acids such as alkylbenzene-sulphonic acids, e.g.
  • n-decylbenzene-sulphonic acid n-dodecylbenzene-sulphonic acid n-tetradecylbenzene-sulphonic acid n-hexadecylbenzene-sulphonic acid n-octadecylbenzene-sulphonic acid [2-(propyl)-heptyl]benzene-sulphonic acid [Z-(butyl)-octyl]-benzene-sulphonic acid [2- (amy1)-nonyl] -benzene-sulphonic acid Substituted benzene-sulphonic acids, e.g.
  • acylated aminocarboxylic acids e.g.
  • the chlorinated hydrocarbon after-treatment baths should contain, in addition to the compounds which are interfaceactive in chlorinated hydrocarbons and convert the dyestuffs used into a .form soluble or dispersible in chlorinated hydrocarbons, small amounts of water, e.g. 0.01-4 percent by weight, referred to the weight of the chlorinated hydrocarbons, and possibly also 0.00 1-2 percent by weight of anon-ionic emulsifier, referred to the weight of the chlorinated hydrocarbons.
  • non-ionic emulsifiers there may be used the commercial non-ionic emulsifiers; for example, reaction prodducts of 1 mol of fatty alcohols, fatty acids, fatty amines, fatty acid amides, fatty acid alkanolamides, fatty acid glycerides, alkyl-phenols, alkyl-benzyl-phenols, alkyl-arylbenzyl-phenols, aryl-styryl-phenols or abietic acid, with 5-100 mol ethylene oxide; and also fatty acid esters of aliphatic polyhydroxy compounds and fatty acid alkanolamides.
  • the chlorinated hydrocarbon after-treatment baths should also contain 0.001-8 percent by weight, referred to the weight of the chlorinated hydrocarbons, of water-miscible organic solvents, such as isopropanol, benzyl alcohol, phenoxy-ethanol, acetonitrile, hydroxypropionitrile, dimethyl sulphoxide, dimethyl formamide or methyl glycol acetate; and to add to the chlorinated hydrocarbon aftertreatment baths 0.0l-0.5 percent by weight, referred to the weight of the chlorinated hydrocarbons, of acetic acid when after-treating dyeings and prints obtained with cationic dyestuffs, and 0.0l-0.5 percent by weight, referred to the Weight of the chlorinated hydrocarbons, of mono-, dior triethanolamine and/or 0.01-1 percent by weight, referred to the weight of the chlorinated hydrocarbons, of acetic acid when after treating dyeings or prints obtained with acidic dyestuffs, ani
  • the process according to the invention is suitable for the dyeing with cationic dyestuffs as well as for the dyeing with acid dyestuffs, anionic, sulpho group-free metal complex dyestuffs and sulpho group-containing reactive dyestuffs.
  • Suitable cationic dyestuffs are methine, azomethine, hydrazone, azacyanine, triarylmethane, xanthene, thioxanthene, acridine, oxazine, thiazine and phenazine dyestuffs; furthermore, the basic dyestuffs of the azo, anthraquinone or phthalocyanine series, such as are described e.g. in Colour Index, vol. 1, 2nd Edition (1956), pages 1617- 1654, and in the Supplement of 1963, and also in French patent specification No. 1,480,930.
  • Suitable acid dyestuffs are all water-soluble dyestuffs of the azo, anthraquinone, triphenyl-methane and phthalocyanine series which contain up to four sulpho groups;
  • examples of anionic sulpho group-free metal complex dyestuffs are the sulpho group-free 1:2 metal complex dyestuffs of the azo and triphenylmethane series which contain at least two groups capable of dissociation; and the sulpho group-containing reactive dyestuffs comprise e.g.
  • water-soluble dyestuffs of the azo, anthraquinone and phthalocyanine series which contain at least one fibrereactive group, for example, a monochloro-triazinyl, dichlorotriazinyl, dichloro-quinoxalinyl, trichloro-pyrimidinyl, difluoro-chloro-pyrimidinyl, u-bromoacrylamide group or the fl-hydroxyethyl-sulphuric acid semi ester group.
  • thickening agents are required for preparing the dyestutf emulsions, thickening agents poor in body are preferred for the process according to the invention.
  • the process according to the invention is suitable for the dyeing and printing of all textile materials which can be dyed or printed with the aforesaid dyestuffs.
  • these include, for example, the textile materials of polyacrylonitrile, polyester, cellulose 2 /2-acetate, cellulose triacetate, synthetic polyamides and silk, which can be dyed with basic dyestuffs; the textile materials of natural or regenerated cellulose such as cotton, staple fibre and rayon, cellulose 2 /2-acetate, cellulose triacetate, of natural polyamides such as wool and silk, and of synthetic polyamides such as polyhexamethylenediamine adipate, polycaprolactam or poly-a-aminoundecanoic acid, which can be dyed with acid, metal complex and reactive dyestuffs.
  • the present process has proved particularly satisfactory for the dyeing and printing of mixtures of these types of fibres, e.g. mixtures of polyacrylonitrile/ staple fibre, polyester/ cotton, polyester/staple fibre, polyamide/ staple fibre, polyamide/cotton, cellulose 2 /z-acetate/staple fibre, cellulose triacetate/staple fibre or polyacr'ylonitrile/polyester.
  • these types of fibres e.g. mixtures of polyacrylonitrile/ staple fibre, polyester/ cotton, polyester/staple fibre, polyamide/ staple fibre, polyamide/cotton, cellulose 2 /z-acetate/staple fibre, cellulose triacetate/staple fibre or polyacr'ylonitrile/polyester.
  • the textile materials may be present in various stages of processing, e.g. as threads, ribbons, combed material, yarn, fabrics, knitted fabrics or ready-made goods.
  • chlorinated hydrocarbons expediently used in the after-treatment baths of the process according to the invention are aliphatic chlorinated hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride,
  • the process according to the invention is carried out by applying the dyestuffs to the textile materials by means of the dyestuff emulsions according to the exhaust, spray, padding or printing process at temperatures from 20 to 120 C. Subsequently, possibly after a conventional heat treatment such as drying, steaming or thermosolising, the textile materials are subjected in a continuous or discontinuous operation to an after-treatment in chlorinated hydrocarbon solutions containing interface-active compounds which convert the dyestuffs used into a form soluble or dispersible in chlorinated hydrocarbons. Optionally, this after-treatment is followed by rinsing in pure chlorinated hydrocarbon.
  • any nonfixed dyestuifs or dyeing auxiliaries are so completely removed from the textile materials that, after separation of the wash liquor and removal of the last solvent residues by blowing out with air or steam, the materials can be stored without any further after-treatment.
  • the emulsions to be used as dyebaths or printing pastes may either contain water as a continuous phase and the chlorinated hydrocarbons as a discontinuous phase, or they may contain the chlorinated hydrocarbons as a continuous phase and water as a discontinuous phase.
  • the aqueous phase is a solution of water-soluble dyestuffs
  • the chlorinated hydrocarbon phase may be a solution of a dyestuif soluble in chlorinated hydrocarbons, but it may also be formed by chlorinated hydrocarbons free from dyestuff.
  • the amounts of dyestuff dissolved in the respective phases depend upon the desired depth of colour of the dyeings or prints, upon the solubility of the dyestuffs, and upon whether the exhaust, spray, padding or printing process is applied. In general, amounts of 0.2 to 50 g. of dyestuff per litre of dyestulf emulsion have proved satisfactory.
  • emulsifiers for preparing the dyestulf emulsions there may be used the compounds which usually serve for preparing oil-in-water and water-in-oil emulsions.
  • Nonionic emulsifiers have proved especially satisfactory for the process according to the invention.
  • Suitable non-ionic emulsifiers are the commercial non-ionic emulsifiers, for example, reaction products of 1 mol of fatty alcohols, fatty acids, fatty amines, fatty acid amides, fatty acid alkanolamides, fatty acid glycerides, alkyl-phenols, alkyl-benzyl-phenols, alkyl-aryl-benzyl-phenols, aryl-styryl-phenols or abietic acid, with lmol ethylene oxide; furthermore, fatty acid esters of aliphatic polyhydroxy compounds and fatty acid alkanolamides.
  • the amounts of emulsifier required for preparing and stabilising the emulsions should not exceed 10 percent by weight, referred to the weight of the emulsions, and should preferably amount to 0.2 to 5 percent by Weight.
  • the dyestuif emulsions may contain the usual dyeing auxiliaries, e.g. urea.
  • the amounts of these auxiliaries depend on the dyestuffs used and on the dyeing process. In general, they amount to about 10 to 500 percent by weight, referred to the weight of the dyestuffs.
  • the emulsions can be prepared in the usual way. It has proved expedient to prepare the solutions forming the two phases separately and to emulsify, after the addition of the emulsifiers, with the aid of rapid stirrers or turbomixers.
  • Chlorinated hydrocarbons which can serve for the preparation of the dyestulf emulsions are those chlorinated hydrocarbons which are also suitable for the after-treatment baths. Tetrachloroethylene, trichloroethylene and l,1,l-trichloropropane have proved especially satisfactory also in the dyestuif emulsions.
  • the process according to the invention combines the advantages of dyeing from aqueous media (use of conventional dyestuffs, good fastness properties of the resultant dyeings) with the advantages of dyeing from organic solvents (unimpaired appearance of the goods, virtually no occurrence of waste water), wthout having the disadvantages of these processes.
  • a particular advantage of the process according to the invention consists in that textile materials can be dyed in the chlorinated hydrocarbon medium in a single bath with water-soluble dyestuffs and with dyestuffs soluble in chlorinated hydrocarbons.
  • the process according to the invention is therefore eminently suitable for the dyeing and printing of materials of cellulose fibres and of mixtures thereof with synthetic fibres with the use of water-soluble reactive dyestuffs for the cellulose fibre component and of disperse dyestuffs soluble in chlorinated hydrocarbons for the synthetic fibre component, and well as for the dyeing and printing of polyacrylonitrile/polyester fibre mixtures with the use of cationic water-soluble dyestuffs for the polyacrylonitrile component and of disperse dyestuffs for the polyester fibre component.
  • the dyeings must therefore be rinsed with aqueous liquors.
  • aqueous wash liquors By using aqueous wash liquors, however, the advantages of dyeing from organic solvents (unimpaired appearance of the goods, slight occurrence of waste water) are cancelled out.
  • the process according to the invention has not only the advantage of permitting dyeing with water-soluble dyestuffs and with dyestuffs soluble in chlorinated hydrocarbons from chlorinated hydrocarbon/water emulsions; it has primarily the advantage that, due to the after treatment with the chlorinated hydrocarbon solutions containing compounds which convert the dyestuffs into a form soluble or dispersible in chlorinated hydrocarbons, dyeing with water-soluble dyestuffs, e.g. reactive dyestuffs and cationic dyestuffs, without having recourse to aqueous baths, yields dyeings of the same good fastness to wet processing as is achieved when dyeing from aqueous baths.
  • water-soluble dyestuffs e.g. reactive dyestuffs and cationic dyestuffs
  • EXAMPLE 1 A polyester/cotton mixed fabric (65:35) is padded with an emulsion consisting of parts of the dyestuff XVI 2 parts nonylphenol pentadecaethylene glycol ether 1 part oleic acid ethanolamide parts of the dyestuff XIII 14 60 parts urea 8 parts sodium bicarbonate 94 parts of water and 800 parts perchloroethylene (liquor absorption dried at 80 C. for 1 minute and thermosolised at C. for 30 seconds.
  • the fabric then passes, with a time of residence of 1.5 minutes each time, through four successive closed washing aggregates which operate according to the counter-current principle and contain a solution at 55 C. which consists of 4 parts of the compound of the formula 1 part of water 5 parts of 30% acetic acid and 990 parts perchloroethylene and is mechanically agitated.
  • the liquor ratio for this after-treatment amounts to 1:50.
  • the fabric is freed from the adhering solvent residues by blowing with hot air, and stored. A clear yellow/red bicolour dyeing of good fastness properties is obtained. No waste Water occurs in the after-treatment.
  • EXAMPLE 2 A polyester/polyacrylonitrile mixed fabric (50:50) is padded with an emulsion consisting of 20 parts of the dyestulf I 10 parts of the dyestufi XVI 4 parts methyl glycol acetate 4 parts glylcerol monoacetate 1 part oleic acid ethanolamide 3 parts nonylphenol decaethylene glycol ether 10 parts of 60% acetic acid 148 parts of water and 800 parts perchloroethylene (liquor absorption 80%) and thermosolised at 180 C. for 1 minute.
  • the fabric web successively passes, in a liquor ratio of 1:50 and With a time of residence of 2 minutes each time, through four solutions of 5 parts sodium dodecyl-benzene sulphonate 0.5 part of 60% acetic acid and 5 parts of water in 989.5 parts perchloroethylene the invention, then the non-fixed, perchloroethylene-insoluble dyestufi is not removed from the fabric and the fastness properties of the resultant dyeing are therefore unsatisfactory.
  • EXAMPLE 3 A polyacrylonitrile fabric is padded with an emulsion consisting of 20 parts of the dyestuff II 2 parts oleyl alcohol eicosaethylene glycol ether 12 parts B-cyanoethyl formamide 4 parts nonylphenol decaethylene glycol ether 10 parts of 60% acetic acid, parts of water and 852 parts perchloroethylene,
  • the fabric is then treated in a liquor ratio of 1:100 in a bath consisting of 10 parts of the compound of the formula CH3-(CHz) sCI-Ig O O /P CH3-(CHB) ltl-CHgO 10 parts of water and 980 parts perchloroethylene at 55 C. for 6 minutes, subsequently rinsed twice with fresh perchloroethylene and, after separating the liquor, freed from the perchloroethylene adhering to the fibre by blowing with steam. Without the occurrence of waste water, there is obtained a red dyeing which is rinsed clear and has the same fastness properties as a dyeing rinsed with an aqueous Washing liquor.
  • a polyacrylonitrile fabric is padded with an emulsion consisting of 15 parts of the dyestulf III 10 parts fi-cyanoethyl formamide 3 parts nonylphenol-decapentaethylene glycol ether 2 parts oleyl alcohol eicosaethylene glycol ether 100 parts of water and 870 parts perchloroethylene (liquor absorption 100%) and steamed at 102 C. for 20 minutes.
  • the polyacrylonitrile fabric is then passed in a liquor ratio of 1:50 through four successive after-treatment baths which have been heated to 50 C. and operate according to the counter-current principle, each containing 1 part sodium dodecylbenzene sulphonate 3 parts of water and 0.05 part of glacial acetic acid in 996 parts perchloroethylene.
  • the fabric is subsequently rinsed with pure perchloroethylene, the rinsing liquor is separated and the adhering solvent driven otf by blowing with steam.
  • the blue dyeing obtained without the occurrence of waste water has the same fastness properties as a corresponding dyeing aftertreated in aqueous baths.
  • EXAMPLE 5 A polyacrylonitrile fabric is printed with a printing paste of the composition parts of the dyestntf IV parts di-fi-cyanoethyl formamide 30 parts thiodiglycol 2 parts nonylphenol decaethylene glycol ether 30 parts of 30% acetic acid 30 parts of water and 873 parts perchloroethylene,
  • the printed fabric is then mechanically moved about in a liquor ratio of 1:50 for 3 minutes in a bath which has been heated to 50 C. and consists of 5 parts of a compound of the formula a- (CH1) 16-0 o1;rcH,-cm-o o 0 H CH3 5 parts of water and 990 parts perchloroethylene and subsequently treated in a liquor ratio of 1:50 for 3 minutes in a second bath which has likewise been heated to 50 C.
  • the perchloroethylene is then separated and the residues of perchloroethylene adhering to the fabric are removed by blowing with steam.
  • EXAMPLE 6 A fabric of anion-modified polyester (Dacron 64) is padded with an emulsion consisting of 20 parts of the dyestuif V 60 parts ethylene-cyanohydrin 3 parts formamide 10 parts of glacial acetic acid 50 parts of water 3 parts nonylphenol-pentadecaethylene glycol ether and 854 parts perchloroethylene (liquor absorption dried at 100 C. for 1 minute and thermosolised at 200 C. for seconds.
  • the dyed fabric is subsequently mechanically moved about in a liquor ratio of 1:50 to 2 minutes in an aftertreatment bath which has been heated to 55 C. and has the composition 1 part of technical oleic acid 1 part oleyl alcohol heptadecaethylene glycol ether 1 part sulphosuccinic acid dioctyl ester and 4 parts of water in 993 parts perchloroethylene,
  • a polyacrylonitrile fabric is padded with an emulsion consisting of 10 parts of the dyestufi VI 11 parts of 85% formic acid 9 parts of 60% acetic acid 12 parts ethylene-cyanohydrin 8 parts glycerol monoacetate 8 parts methyl glycol acetate 4 parts nonylphenol decaethylene glycol ether 88 parts of water and 850 parts perchloroethylene (liquor absorption 100%), dried at 100 C. for 1 minute and thermosolised at 200 C. for 1 minute. 15
  • the fabric then passes through 5 successive wash baths which have been heated to 50 C., each containing 5 parts of a mixture of 19.5 parts of the compound of the formula (CH (CH CO-NH-CH CH NH 1 part stearic acid 2 parts of the compound of the formula CH; 0.5 parts oleyl alcohol heptadecaethylene glycol ether 3 parts of glacial acetic acid 19.5 parts isopropanol and (2) When 5 parts of the mixture are replaced with 5 parts of one of the following compounds of the Formulae a-g:
  • the fabric is then treated in a liquor ratio of 1:50 for 3 minutes in an after-treatment bath at 50 C. consisting of 5 parts of the N,N-di-octadecyl-N,N-dimethyl ammonium salt of sulphated rapeseed oil 5 parts of water and 990 parts perchloroethylene and subsequently in an after-treatment bath consisting of 1 part of the N,N-di-octadecyl-N,N-dimethyl ammonium salt of sulphated rapeseed oil 1 part of water and 998 parts perchloroethylene.
  • rapeseed oil are replaced with 5 parts and 1 part, respeci tively, of a mixture of 3 parts of the compound of the formula c CH CH CH s( 2)l!16 ⁇ 2@/ a 9 parts isopropanol,
  • EXAMPLE 10 A mixed fabric (50:50) of a polyamide which can be dyed with basic dyestuffs and a polyamide which can be dyed with acidic dyestuffs is padded with an emulsion consisting of 10 parts of the dyestulf I 10 parts of the dyestuif IX 4 parts of the reaction product of 1 mol oleyl alcohol with 50 mol ethylene oxide 4 parts nonylphenol decaethylene glycol ether 3 parts of a mixture consisting of 20 parts of a compound of the formula CgHs 40 parts oleyl alcohol eicosaethylene glycol ether and 40 parts ethyl hexanol 5 parts of 60% acetic acid 80 parts of water and 884 parts perchloroethylene with a liquor absorption of 70%, dried at 80 C. for 1 minute and steamed at 105 C. for 3 minutes.
  • the fabric web then successively passes in a liquor ratio of 1:30 with a time of residence of 2 minutes each time through two after-treatment baths which are mechanically agitated and have been heated to 50 C. and which consist of 0.75 part of the N,N-di-octadecyl-N,N-dimethyl ammonium salt of sulphated rapeseed oil 0,75 parts of a compound of the formula CHs-CONH-SOP(CH2)M-CH
  • EXAMPLE 1 A Turkish towelling fabric of cotton is padded with an emulsion consisting of 40 parts of the dyestufl? X parts urea 98 parts of water 10 parts sodium bicarbonate 5 parts nonylphenol decaethylene glycol ether and 767 parts perchloroethylene,
  • the fabric is subsequently after-treated in a liquor ratio of 1:40 for 3 minutes each time in two successive baths which have been heated to 50 C. and consists of 5 parts of a compound of the formula 5 parts of 60% acetic acid 10 parts of water and 980 parts perchloroethylene and subsequently rinsed at the same temperature for 2 minutes with fresh perchloroethylene.
  • the solvent residues are removed by blowing with steam. Without the occurrence of waste water, there is obtained a yellow dyeing which has been rinsed clear and has faultless fastness properties.
  • EXAMPLE 12 A polyacrylonitrile/cotton mixed fabric (50:50) is padded with an emulsion consisting of 9 parts of the dyestuff XI 26 parts of ethylene-'cyanohydrin 15 parts formamide 2 parts nonylphenol decaethylene glycol ether 1 part oleic acid ethanolamide 60 parts urea parts of water and 804 parts perchloroethylene (liquor absorption dried at 80 C. for 90 seconds and thermosolised at 202 C. for 1 minute.
  • the fabric subsequently passes with a time of residence of 90 seconds each time through 6 successive aftertreatment baths which have been heated to 50 C. and consist of 5 parts of the compound of the formula CH3(CH2)16 C0 NH (CH2)3 N (CH3)2 15 parts of water and 980 parts perchloroethylene.
  • EXAMPLE 13 A staple fibre fabric is padded with an emulsion consisting of 30 parts of the dyestuif XII 4 parts nonylphenol pentadecethylene glycol ether 80 parts urea parts sodium bicarbonate 90 parts of water and 786 parts perchloroethylene (liquor absorption 80%), dried at 80 C. for 1 minute 54 parts of a mixture consisting of 0.6 parts sodium carbonate 10.4 parts of water 5 parts urea 32 parts perchloroethylene and 6 parts of a mixture consisting of 30 parts sodium paraflin sulphonate 2.5 parts sodium dodecyl-benzene sulphonate 17.5 parts of the sulphuric acid ester of a sperm oil alcohol 12.
  • the fabric is subsequently after-treated in a liquor ratio of 1:50 for 2 minutes each time in 5 successive baths which have been heated to 55 C. and consisting of
  • the fabric is then after-treated in a liquor ratio of 1:20 with a time of residence of 10 minutes with a bath which has been heated to 50 C. and consists of 5 parts of the compound of the formula 5 parts of a compound of the formula CH CH 0CH NCH s( 92 2 H a 019 2 5 parts isopropanol 5 parts of water 5 parts of 60% acetic acid and 985 parts perchloroethylene CHa-(CHz) 0CH:NCH1
  • EXAMPLE 14 100 parts of a polyester/cotton mixed fabric (67:33) are printed in a pressure Winding frame at C. for 30 minutes with an emulsion consisting of 5 parts of water 2 parts of 60% acetic acid and 988 parts perchloroethylene The fabric is subsequently rinsed with pure perchloroethylene at C. for 2 minutes. After separating the rinsing liquor, the fabric is freed from the adhering solvent by blowing with steam. There is obtained a red/ blue bicolour dyeing which has the same fastness properties as a dyeing washed with aqueous wash baths.
  • EXAMPLE 15 A cotton fabric is padded with an emulsion consisting of 40 parts of the dyestutf XIV 3 parts nonylphenol decaethylene glycol ether parts urea 10 parts sodium carbonate 100 parts of water and 787 parts perchloroethylene (liquor absorption dried at 80 C. for 1 minute and steamed at 102 C. for 5 minutes.
  • the fabric is subsequently after-treated in a liquor ratio of 1:50 with a time of residence of 2 minutes each time in 3 successive baths which have been heated to 55 C and consist of 5 parts of the aminoxide of the formula 10 parts of water and 985 parts perchloroethylene.
  • the fabric is then rinsed with pure perchloroethylene at 55 C., for 2 minutes. After separating the rinsing liquor,
  • the fabric is freed from the adhering perchloroethylene residues in an air current.
  • a clear yellow dyeing is obtained without the occurrence of Waste water.
  • EXAMPLE 16 A polyester/cotton mixed fabric (65:35) is padded with an emulsion consisting of 12 parts of the dyestuff XVI 2 parts nonylphenol decaethylene glycol ether 1 part oleic acid ethanol amide 20 parts of the dyestulf VII 60 parts urea 8 parts sodium bicarbonate 97 parts of water and 800 parts perchloroethylene (liquor absorption 80% dried at 120 C. for 60 seconds and thermosolised at 18.0 for 60 seconds.
  • the fabric then passes through 5 successive washing aggregates which operate according to the counter-current principle and contains a solution at 55 C. consisting of 5 parts of the compound of the formula 5 parts of water and 990 parts perchloroethylene.
  • the liquor ratio for the after-treatment amounts to 1:100.
  • the fabric is subsequently rinsed with a mixture at 55 C. consisting of 990 parts perchloroethylene 5 parts of 60% acetic acid and 5 parts of water.
  • the fabric After separating the rinsing liquor, the fabric is freed from the adhering solvent residues by blowing with air. Without the occurrence of waste water there is obtained a clear dyeing with a red/yellow pattern which has the same fastness properties as a dyeing after-treated with aqueous liquors.
  • EXAMPLE 17 A polyester/ staple fibre mixed fabric (70:30) is padded with an emulsion consisting of 20 parts of the dyestutf XVI 15 parts of the dyestutf XIV 50 parts urea 70 parts nonylphenol hexaethylene glycol ether 5 parts sodium bicarbonate 60 parts of water and 780 parts perchloroethylene (liquor absorption 80% dried at 120 C. for 90 seconds and thermosolised at 180 C. for 90 seconds.
  • the fabric is subsequently after-treated in a liquor ratio of 1:50 for 5 minutes in bath at 55 C. consisting of 5 parts of the compound of the formula I [CH -(CH2)16 CO-NH-CHn-CHg]g/IgT-CHg-CHg-CHn-SOa 10 partsof 30% acetic acid and 985 parts perchloroethylene are replaced with (a) 5 parts of a mixture o f equal parts of the compound of the formula and oleic acid or (b) 5 parts of a mixture of equal parts of the compound of the formula and the compound of the formula (c) 5 parts of a mixture of equal parts of the compound of the formula and the compound of the formula or (d) 5 parts of the N,N-dioctadecyl-N,N-dimethyl ammonium salt of sulphated rapeseed oil or (e) 5 parts of a mixture of 18.5 parts of the compounds of the formula CH3 e [GH3 (CH2)10 CHB] 2 ⁇ N/ :
  • the fabric then passes in a liquor ratio of 1:50 and with a time of residence of 2 minutes each time through 4 successive after-treatment baths which have been heated to 55 C. and consist of 6 parts N,N-di-eicosyl-N,N-dimethyl ammonium bromide 6 parts of water 1 part octadecyl alcohol heptadecaethylene glycol ether and 987 parts perchloroethylene.
  • the fabric web then passes with a time of residence of 1 minute through a rinsing bath of pure perchloroethylene which has been heated to 50 C. After separating the rinsing liquor, the fabric is freed from the adhering perchloroethylene residues by blowing with hot air. The resultant red dyeing is rinsed clear without the occurrence of waste water and has the same fastness properites as a dyeing rinsed with water.
  • EXAMPLE 19 A cellulose/poly-e-caprolactam mixed fabric (50:50) is padded with an emulsion consisting of 20 parts of the dyestufi VII 20 parts of the 1:2 chromium complex of the dyestufi XVHI 3 parts nonylphenol decaethylene glycol ether 6 parts sodium bicarbonate 80 parts urea 100 parts of water and 771 parts perchloroethylene (liquor absorption 40%), dried at 100 C. for 1 minute and thermosolised at 192 C. for 60 seconds.
  • the fabric web then successively passes in a liquor ratio of 1:50 and with a time of residence of 2 minutes each time through 4 after-treatment baths which are mechanically agitated and have been heated to C. and consist of 4 parts of the compound of the formula ooz- 1 part of the compound of the formula CHz-CHg-OH e CHg-(CHz)mCHqNHCOOCHgCHz-N 01 CHn-CHa-OH 1 part of the compound of the formula 7 parts of 30% acetic acid and 987 parts perchloroethylene CONSTITUTIONS OF THE DYESTUFFS I-XVIII USED IN THE EXAMPLES Number Constitution II (32H:
  • R is an alkyl, alkenyl or aralkyl radical of 12-28 carbon atoms or one of the aforesaid radicals containing oxygen, sulfur or nitrogen;
  • R and R independently of one another, are unsubstituted or substituted alkyl, alkenyl, or aralkyl radicals which contain 1-28 carbon atoms or one of the aforesaid radicals containing oxygen, sulfur or nitrogen;
  • R is substituted or unsubstituted C C -alkyl, C -C alkenyl, cycloalkyl or aralkyl or together with R forms a non-aromatic 5- or 6-membered heterocycle; with the proviso that the sum of carbon atoms in R R R and R is 20 to 60; and
  • X- is an anion
  • the interface-active compound is a quaternary ammonium compound of the formula in which R; is an alkyl, alkenyl or aralkyl radical of 12-28 carbons, or one of the aforesaid radicals containing oxygen, sulfur or nitrogen;
  • R is an unsubstituted or substituted alkyl, alkenyl or aralkyl radical of 1-28 carbon atoms or one of the aforesaid radicals containing oxygen, sulfur or nitrogen;
  • R is unsubstituted or substituted C C -alkyl, C C
  • Z is an alkylene radical which contains l8 carbon atoms, a C C -alkylene which contains oxygen atoms or 1,4- bis-methylene-benzene radical; with the proviso that the sum of carbon atoms in R R R and R and Z is 20 to 60; and
  • the interface-active compound is an amine of the formula in which R; is an alkyl, alkenyl or aralkyl radical of 12-28 carbon atoms or one of the aforesaid radicals containing oxygen, sulfur or nitrogen;
  • R is an unsubstituted or substituted C C -alkyl, C C
  • alkenyl, cycloalkyl or aralkyl radical alkenyl, cycloalkyl or aralkyl radical
  • R is hydrogen, an unsubstituted or substituted alkyl, alkenyl or aralkyl radical of 1-28 carbon atoms or one of the aforesaid radicals containing oxygen, sulfur or nitrogen, or R together with R forms a 5- or G-membered non-aromatic heterocycle; with the proviso that the sum or carbon in R R and R is 20 to 60.
  • the interface-active compound is an aminoxide of the formula in which R is an alkyl, alkenyl or aralkyl radical of 12-28 carbon atoms or one of the aforesaid radicals containing oxygen, sulfur or nitrogen;
  • R is an unsubstituted or substituted alkyl, alkenyl or aralkyl radical of 1-28 carbon atoms or one of the aforesaid radicals containing oxygen, sulfur or nitrogen;
  • R is an unsubstituted or substituted C -C -alky1, or C -c -alkenyl, cycloalkyl or aralkyl radical or together with R forms a non-aromatic 5- or 6-membered heterocycle; with proviso that the sum of carbon atoms in R R and R is 20 to 60.
  • the aliphatic chlorinated hydrocarbon solution contains a compound selected from the group consisting of 0.01% to 1.0% by weight of acetic acid, 0.01% to 0.5% by weight of monoethanolamine 0.01% to 0.5% by weight of diethanolamine and 0.01% to 0.5% by weight of triethanolamine.

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  • Textile Engineering (AREA)
  • Coloring (AREA)
US00070514A 1969-09-11 1970-09-08 Process for the dyeing and printing of textile materials Expired - Lifetime US3764262A (en)

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DE19691945965 DE1945965A1 (de) 1969-09-11 1969-09-11 Verfahren zum Faerben und Bedrucken von Textilmaterialien

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US (1) US3764262A (enrdf_load_stackoverflow)
AT (1) AT312551B (enrdf_load_stackoverflow)
BE (1) BE755978A (enrdf_load_stackoverflow)
CA (1) CA940659A (enrdf_load_stackoverflow)
CH (2) CH1349870A4 (enrdf_load_stackoverflow)
DE (1) DE1945965A1 (enrdf_load_stackoverflow)
FR (1) FR2061674B1 (enrdf_load_stackoverflow)
GB (1) GB1273494A (enrdf_load_stackoverflow)
NL (1) NL7013342A (enrdf_load_stackoverflow)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3894842A (en) * 1972-03-10 1975-07-15 Hoechst Ag Process for preparing dyeings and prints fast to light on synthetic fibers
US3900286A (en) * 1971-11-19 1975-08-19 Ciba Geigy Ag Dyestuff preparations and processes for the dyeing of synthetic organic material
US3954399A (en) * 1972-03-28 1976-05-04 Sumitomo Chemical Company, Limited Process for dyeing nitrogen-containing fibers
US3957433A (en) * 1973-05-14 1976-05-18 Imperial Chemical Industries Limited Dyeing additives
US3995996A (en) * 1972-04-27 1976-12-07 Bayer Aktiengesellschaft Agents for improving wet fastness properties
US4369041A (en) * 1980-05-12 1983-01-18 Vyzkumny Ustav Zuslechtovaci Technique for dyeing and printing of textiles with quaternary ammonium compound
US4453943A (en) * 1982-04-02 1984-06-12 Ciba-Geigy Corporation Solid formulations of anionic dyes

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3900286A (en) * 1971-11-19 1975-08-19 Ciba Geigy Ag Dyestuff preparations and processes for the dyeing of synthetic organic material
US3894842A (en) * 1972-03-10 1975-07-15 Hoechst Ag Process for preparing dyeings and prints fast to light on synthetic fibers
US3954399A (en) * 1972-03-28 1976-05-04 Sumitomo Chemical Company, Limited Process for dyeing nitrogen-containing fibers
US3995996A (en) * 1972-04-27 1976-12-07 Bayer Aktiengesellschaft Agents for improving wet fastness properties
US3957433A (en) * 1973-05-14 1976-05-18 Imperial Chemical Industries Limited Dyeing additives
US4369041A (en) * 1980-05-12 1983-01-18 Vyzkumny Ustav Zuslechtovaci Technique for dyeing and printing of textiles with quaternary ammonium compound
US4453943A (en) * 1982-04-02 1984-06-12 Ciba-Geigy Corporation Solid formulations of anionic dyes

Also Published As

Publication number Publication date
NL7013342A (enrdf_load_stackoverflow) 1971-03-15
BE755978A (fr) 1971-02-15
CA940659A (en) 1974-01-29
DE1945965A1 (de) 1971-03-25
FR2061674B1 (enrdf_load_stackoverflow) 1974-08-23
FR2061674A1 (enrdf_load_stackoverflow) 1971-06-25
GB1273494A (en) 1972-05-10
CH540392A (de) 1973-02-28
AT312551B (de) 1974-01-10
CH1349870A4 (enrdf_load_stackoverflow) 1973-02-28

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