EP0312493B1 - Procédé de teinture de fibres en polyamide naturelles avec des colorants réactifs - Google Patents

Procédé de teinture de fibres en polyamide naturelles avec des colorants réactifs Download PDF

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Publication number
EP0312493B1
EP0312493B1 EP88810631A EP88810631A EP0312493B1 EP 0312493 B1 EP0312493 B1 EP 0312493B1 EP 88810631 A EP88810631 A EP 88810631A EP 88810631 A EP88810631 A EP 88810631A EP 0312493 B1 EP0312493 B1 EP 0312493B1
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Prior art keywords
process according
formula
hydrogen
carbon atoms
radical
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German (de)
English (en)
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EP0312493A1 (fr
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Walter Dr. Mosimann
Dieter Dr. Mäusezahl
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Novartis AG
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Ciba Geigy AG
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Classifications

    • 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
    • D06P1/38—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 reactive dyes
    • 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
    • D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/60—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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing polyethers
    • D06P1/613—Polyethers without nitrogen
    • D06P1/6131—Addition products of hydroxyl groups-containing compounds with oxiranes
    • D06P1/6133—Addition products of hydroxyl groups-containing compounds with oxiranes from araliphatic or aliphatic alcohols
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/10—Material containing basic nitrogen containing amide groups using reactive dyes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/917—Wool or silk

Definitions

  • a single-bath process in which pieces of wool with an aqueous liquor, which is obtained by mixing 75 liters of a 50% aqueous solution, which is a quaternized condensation product of a fatty amine and Contains 7 moles of ethylene oxide and a condensation product esterified with amidosulfonic acid from the same fatty amine and 7 moles of ethylene oxide, and obtained from 25 liters of a 25% aqueous solution of a condensation product of 1 mole of octadecyl alcohol and 35 moles of ethylene oxide. After adding a reactive dye and other aids, the wool pieces are dyed in the same bath.
  • the present invention relates to a process for dyeing natural polyamide fibers, in particular wool with reactive dyes, using the exhaust method, in which the fiber material is firstly derived from acids with a dyeing auxiliary consisting of a combination of (a) quaternized ammonium compounds from polyglycol compounds and (b) from at least dibasic oxygen acids Esters or their salts of polyglycol compounds, both the quaternary ammonium compounds and the acidic esters being derived from an aliphatic amine which has 12 to 24 carbon atoms in the aliphatic radical and pretreated in a bath in the presence (c) of a fatty alcohol polyalkylene glycol ether and is then dyed in the same bath after addition of the dye, characterized in that the fatty alcohol polyalkylene glycol ether of the formula in which R is an aliphatic radical having at least 8 carbon atoms, "alkylene” represents the ethylene radical or propylene radical and m is 3 to 25.
  • a dyeing auxiliary consist
  • Both components (a) and (b) and the polyglycol ether (c) can be present as individual compounds or as mixtures with one another.
  • the quantitative ratio of the combination of components (a) and (b) to component (c) is advantageously between 2: 1 and 1: 1, preferably 1.6: 1 and 1.2: 1.
  • the auxiliaries used in the process according to the invention are particularly suitable for improving fiber levelness and also enable the dye baths to be completely exhausted.
  • the addition of the nonionic component (c) is used in particular to prevent addition products or precipitates formed from the dye and auxiliary mixture, which then dissolve in the wool fat still present and attach to the dyeing apparatus.
  • the substituent R advantageously represents the hydrocarbon radical of an unsaturated or saturated aliphatic monoalcohol with 8 to 24 carbon atoms.
  • the hydrocarbon radical can be straight-chain or branched.
  • R is preferably an alkyl or alkenyl radical having 12 to 22 carbon atoms.
  • aliphatic saturated monoalcohols natural alcohols such as e.g. Lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, arachidyl alcohol or behenyl alcohol, as well as synthetic alcohols, e.g. Oxo alcohols such as, in particular, 5-methylheptan-3-ol, 2-ethyl-hexanol, octan-2-ol, trimethyl-nonyl alcohol, decanol, hexadecyl alcohol or linear primary alcohols (alfoles) with 8 to 18 carbon atoms are suitable.
  • natural alcohols such as e.g. Lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, arachidyl alcohol or behenyl alcohol
  • synthetic alcohols e.g.
  • Oxo alcohols such as, in particular, 5-methylheptan-3-ol, 2-ethyl-hexanol, octan-2-ol,
  • Unsaturated aliphatic monoalcohols are, for example, dodecenyl alcohol, hexadecenyl alcohol or especially oleyl alcohol.
  • the alcohol residues can be present individually or in the form of mixtures of two or more components, e.g. Mixtures of alkyl and / or alkenyl groups which are derived from soybean fatty acids, palm kernel fatty acids or tallow oils.
  • m is preferably 10 to 20 or especially 12 to 18.
  • Alkylene-O m chains are preferably of the ethylene glycol, propylene ethylene glycol or ethylene propylene glycol type; the former is particularly preferred.
  • the amounts used in which the fatty alcohol polyglycol ethers (c) are present in the dyeing liquors are advantageously from 0.3 to 2.5% by weight, preferably 0.5 to 2% by weight, based on the material to be dyed, depending on the dye .
  • quaternary ammonium salts for component (a) of the auxiliary mixture reaction products of alkylene oxide addition products from aliphatic or araliphatic mono- and / or diamines, which contain tertiary amino groups and an aliphatic radical having 12 to 24 carbon atoms can be used with a quaternizing agent.
  • reaction products of alkylene oxide addition products from aliphatic or araliphatic mono- and / or diamines which contain tertiary amino groups and an aliphatic radical having 12 to 24 carbon atoms can be used with a quaternizing agent.
  • Such compounds are described for example in CH-PS 465 553.
  • Component (a) preferably consists of a quaternary ammonium compound of the formula in which R1 is an aliphatic hydrocarbon radical, preferably an alkyl or alkenyl radical having 12 to 22 carbon atoms, V an optionally substituted alkyl radical, of Z1 and Z2 a hydrogen, methyl or phenyl and the other hydrogen,
  • R1 is an aliphatic hydrocarbon radical, preferably an alkyl or alkenyl radical having 12 to 22 carbon atoms
  • V an optionally substituted alkyl radical, of Z1 and Z2 a hydrogen, methyl or phenyl and the other hydrogen
  • An ⁇ an anion of an inorganic or organic acid and p and s each represent 1 to 100, the sum of p and s being 2 to 100.
  • Acid esters or their salts of compounds of the formula are advantageously suitable as component (b) or a quaternized product of the acidic ester or its salts, in which R2 is an aliphatic hydrocarbon radical having 12 to 22 carbon atoms, in particular 12 to 18 carbon atoms, Z3 and Z4, hydrogen, methyl or phenyl and the other hydrogen and n1 and n2 are integers, the sum n1 + n2 is 2 to 100.
  • the acidic esters can be in the form of mono- or diesters and as free acids or preferably as salts, for example alkali metal salts or ammonium salts.
  • the alkali metal salts are in particular the sodium and potassium salts and the ammonium, trimethylammonium, Monoethanolammonium-, Diethanolammonium- and Triethanolammoniumsalze called.
  • the acidic esters are preferably used as ammonium salts.
  • the acidic esters which can be considered as component (b) and the corresponding starting materials are known from CH-PS 465 553, EP-A-197005, EP-A-235 088 or DE-OS 2 834 686 and can be according to Processes described there are produced.
  • the amine-polyglycol compounds required for the preparation of the quaternary ammonium compounds of the formula (1) and the acidic esters are prepared by adding ethylene oxide, propylene oxide, styrene oxide or their combinations to aliphatic amines which have an aliphatic hydrocarbon radical of 12 to 24 carbon atoms.
  • the quaternary ammonium compounds of the formula (1) are obtained by quaternization of the addition products obtained. Both the alkylene oxide additions and the quaternization can be carried out according to methods known per se.
  • Component (b) is expediently prepared by esterification of the addition products or their quaternary ammonium salts with at least dibasic oxygen acids under conditions such that one or two ester groups, preferably in the form of the salts mentioned, are formed.
  • the polybasic oxygen acids for the formation of the acidic esters can optionally be sulfonated, organic, preferably aliphatic dicarboxylic acids of 3 to 6 carbon atoms, such as maleic acid, malonic acid, succinic acid or sulfosuccinic acid, or in particular polybasic inorganic oxygen acids, such as sulfuric acid or orthophosphoric acid.
  • their functional derivatives such as acid anhydrides, acid halides, acid esters or acid amides can be used. Examples of these functional derivatives are maleic anhydride, chlorosulfonic acid and in particular sulfamic acid.
  • the esterification is generally carried out by simply mixing the reactants with heating, advantageously to a temperature between 50 ° and 100 ° C.
  • the free acids initially formed can then be converted into the corresponding alkali metal or ammonium salts.
  • the conversion into the salts takes place in the usual way by adding bases, e.g. Ammonia, monoethanolamine, triethanolamine or alkali metal hydroxides, e.g. Sodium or potassium hydroxide.
  • bases e.g. Ammonia, monoethanolamine, triethanolamine or alkali metal hydroxides, e.g. Sodium or potassium hydroxide.
  • acidic sulfuric acid esters are prepared directly in the form of their ammonium salts by heating the alkylene oxide addition products, expediently in the presence of urea, with sulfamic acid.
  • Suitable esters contain either an acidic maleic acid ester group or in particular one or two acidic sulfuric acid ester groups, which are preferably in the form of their alkali metal salts or ammonium salts.
  • R1 and R2 are preferably an alkyl or alkenyl radical having 12 to 22 carbon atoms.
  • Z1, Z2, Z3 and Z4 are preferably hydrogen.
  • the sum of p + s and n1 + n2 is each advantageously 5 to 40.
  • V is preferably methyl, ethyl, benzyl, -CH2CONH2 or
  • R1 and R2 are alkyl, it is radicals such as, for example, lauryl, myristyl, cetyl, palmityl, stearyl, arachidyl or behenyl.
  • alkenyl radicals for R1 and R2 are, for example, dodecenyl, hexadecenyl, oleyl or octadecenyl.
  • the radicals R1 and R2 can be derived from chemically uniform amines or from amine mixtures.
  • Dodecylamine (laurylamine), myristylamine, cetylamine, palmitylamine, stearylamine, arachidylamine, behenylamine, lignocerylamine, oleylamine and erucylamine may be mentioned as amines.
  • amine mixtures preference is given to those used in the transfer of natural fats or oils, such as e.g. Palm kernel fat, tallow fat, soybean or coconut oil are formed in the corresponding amines. Tallow fatty amine is preferred. This is a mixture of 30% hexadecylamine, 25% octadecylamine and 45% octadecenylamine.
  • Components (a) and (b) are generally used in a weight ratio of 3: 1 to 1: 3, preferably 1.5: 1 to 1: 1.5.
  • auxiliary mixture consisting of components (a) and (b) are added to the dyebaths range from 0.05 to 5% by weight, preferably 0.5 to 2.5% by weight, based on what is to be dyed Fiber material.
  • X is hydrogen or SO3M
  • M is hydrogen, alkali metal or -NH4, R3 and R4, independently of one another, each alkyl or alkenyl having 12 to 22 carbon atoms, V1 methyl, ethyl, benzyl, -CH2CO- NH2 or (At) ⁇ 1 the chloride or methosulfate ion, s1, p1, n3 and n4 integers, the sum of (p1 + s1) and (n3 + n4) each being from 5 to 15.
  • the mixing ratio is preferably 1: 1.5 to 1.5: 1.
  • V1 is preferably methyl or -CH2CONH2 and in formula (6) X is preferably hydrogen.
  • fiber material made of natural polyamides which can be dyed according to the invention, above all wool, but also mixtures of wool / polyamide, wool / polyester or wool / polyacrylonitrile and silk should be mentioned.
  • the fiber material can be in a wide variety of forms. Examples include: flake, sliver, yarn, woven fabric, knitwear or carpets.
  • the wool can be finished normally or without felt.
  • the organic dyes known under this term regardless of the type of their reactive group - come into consideration as reactive dyes.
  • reactive dyes This colorant class is referred to in the Color Index 3 edition 1971 as "reactive dyes". These are predominantly those dyes which contain at least one group which is particularly reactive with polyhydroxyl fibers (cellulose fibers) or polyamide fibers or wool, a precursor for this or a substituent which is reactive with polyhydroxyl fibers or polyamide fibers.
  • Suitable bases for the reactive dyes are particularly those from the series of mono-, dis- or polyazo dyes including formazan dyes and anthraquinone, xanthene, nitro, triphenylmethane, naphthoquinonimine and phthalocyanine dyes, the azo and phthalocyanine dyes being both metal-free and can also contain metal.
  • Reactive groups and precursors which form such reactive groups include, for example, epoxy groups, the ethyleneimide group, the vinyl grouping in vinylsulfone or in acrylic acid residues and the ⁇ -sulfatoethylsulfone group, the ⁇ -chloroethylsulfone group or the ⁇ -dialkylaminoethylsulfone group.
  • the reactive substituents in reactive dyes are those that are easily removable and leave an electrophilic residue.
  • substituents are 1 or 2 halogen atoms in an aliphatic acyl radical, e.g. in the ⁇ -position or ⁇ - and ⁇ -position of a propionyl radical or in the ⁇ - and / or ⁇ -position of an acrylic acid radical, or 1 to 3 halogen atoms on the following ring system into consideration: pyridazine, pyrimidine, pyridazone, triazine, quinoxaline or phthalazine.
  • Dyes with two or more identical or different reactive groups can also be used.
  • Preferred reactive dyes contain, as reactive substituents, chloroacetyl, ⁇ -bromoacryloyl, ⁇ , ⁇ -dibromopropionyl, 2,4-difluoro-5-chloropyrimidin-6-yl, 2,4-dichloro-1,3,5-triazinyl or 2,4, 5-trichloropyrimidin-6-yl.
  • the reactive dyes can contain acidic, salt-forming substituents, such as carboxylic acid groups, sulfuric acid and phosphonic acid ester groups, phosphonic acid groups or preferably sulfonic acid groups.
  • Reactive dyes with at least two sulfonic acid groups in particular reactive dyes with a metal-free azo base body, which preferably has two to four sulfonic acid groups, are preferred.
  • a preferred embodiment of the process according to the invention is that reactive dyes of the formula in the T1 and T2, independently of one another, are each hydrogen or C1-C4-alkyl and Y1 and Y2 independently of one another, each chloroacetyl, ⁇ -bromoacryloyl, ⁇ , ⁇ -dibromopropionyl, 2,4-dichloro-s-triazinyl, 2,4-difluoro-5-chloropyrimidin- (6) -yl or 2,4,5 -Trichlorpyrimidin-6-yl mean used.
  • Particularly preferred dyes are those in which -NT1Y1 and-NT2Y2 are identical and T1 and T2 are hydrogen.
  • Y1 and Y2 are preferably ⁇ -bromoacryloyl or ⁇ , ⁇ -dibromopropionyl.
  • the coloring takes place after the pull-out procedure.
  • the amount of the dyes added to the dye liquor depends on the desired color strength; in general, amounts of from 0.01 to 10 percent by weight, preferably 0.1 to 5 percent by weight, based on the fiber material used, have proven successful.
  • the liquor ratio can be selected within a wide range, for example 1: 3 to 1: 100, preferably 1: 6 to 1:30.
  • the dye baths can contain mineral acids, e.g. Sulfuric acid or phosphoric acid, organic acids expediently contain aliphatic carboxylic acids such as formic acid, acetic acid, oxalic acid or citric acid and / or salts such as ammonium acetate, ammonium sulfate or sodium acetate.
  • mineral acids e.g. Sulfuric acid or phosphoric acid
  • organic acids expediently contain aliphatic carboxylic acids such as formic acid, acetic acid, oxalic acid or citric acid and / or salts such as ammonium acetate, ammonium sulfate or sodium acetate.
  • the acids are used primarily to adjust the pH of the liquors used according to the invention, which is generally 4 to 7, preferably 4.3 to 6.
  • the dye liquors can also contain other additives, e.g. Wool protection, dispersing and wetting agents as well as defoamers included.
  • the customary dyeing apparatus such as, for example, open baths, combed, strand yarn or packing apparatus, jigger, paddle apparatus, tree dyeing apparatus, circulation or jet dyeing apparatus or reel runners can be used.
  • the dyeing is advantageously carried out at a temperature in the range from 60 to 120 ° C., preferably from 70 ° C. to cooking temperature (100-102 ° C.).
  • the dyeing time is within the usual range and is usually 20 to 120 minutes.
  • the dye liquors are generally given fixing alkalis, e.g. aqueous ammonia, alkali metal hydroxides, alkali metal carbonates or bicarbonates added.
  • alkalis e.g. aqueous ammonia, alkali metal hydroxides, alkali metal carbonates or bicarbonates added.
  • the pH of the dye baths containing alkali is expediently 7.5 to 9, preferably 8 to 8.5.
  • the dyeing of the fiber material is expediently carried out in such a way that the material to be dyed with an aqueous liquor, the acid, the auxiliary mixture of components (a) and (b) and the nonionic additive (c) and a temperature of 40 to 60 ° C. , treated briefly and adding the reactive dye to the same bath.
  • the temperature is then slowly increased in order to dye in a range from 80 to 100 ° C. and for 20 to 90 minutes, preferably 30 to 60 minutes.
  • the dyed material is preferred after the addition of fixing alkalis aqueous ammonia, treated alkaline at 70 to 90 ° C for 10 to 20 minutes.
  • the colored material is pulled out and rinsed, acidified and dried as usual.
  • the dyeing process according to the invention gives uniform and strongly colored dyeings which are also distinguished by good fastness to rubbing and color yields.
  • the other fastness properties of the dyeings such as Light fastness and wet fastness are not adversely affected by the addition of the nonionic component (c).
  • the process according to the invention achieves complete exhaustion of the dyebath without dye precipitations and dyes in the dyebath.
  • the parts are parts by weight and the percentages are percentages by weight.
  • the dye liquor After adding a solution containing 5 kg of a disazo dye of the formula (22), the dye liquor is kept at 40 ° C. for 10 minutes and then heated to 70 ° C. at a heating rate of 1 ° C./min. After a holding time of 15 minutes at 70 ° C, the temperature is raised to 98 ° C. After 90 minutes of dyeing at 98 ° C., the mixture is cooled to 85 ° C., adjusted to pH 8.5 with ammonia and treated at 85 ° C. for 15 minutes. After cooling to 60 ° C, the liquor is drained.
  • the blue-black colored fabric is rinsed as usual, acidified with 1 kg of 85% formic acid and dried.
  • the coloring is irrelevant and has good fastness properties.
  • the dyeing machine and the material carrier (perforated tree) are absolutely clean.
  • the dye liquor After adding a solution containing 5 kg of a dye of the formula and 2 kg of a dye of the formula the dye liquor is kept at 40 ° C. for a further 10 minutes and then heated to 70 ° C. at a heating rate of 1 ° C./min. After a holding time of 15 minutes at 70 ° C, the temperature is raised to 98 ° C. After 90 minutes of dyeing at 98 ° C., the mixture is cooled to 85 ° C., adjusted to pH 8.5 with ammonia and treated at 85 ° C. for 15 minutes. After cooling to 60 ° C, the liquor is drained.
  • the brilliant red colored yarn is rinsed as usual, acidified with 1 kg of 85% formic acid and dried.
  • the coloring is irrelevant and has good fastness properties.
  • the dyeing machine and the material carrier are absolutely clean.
  • the dye liquor After adding a solution containing 2 kg of a dye of the formula 3 kg of a dye of the formula and 2 kg of a dye of the formula the dye liquor is kept at 40 ° C. for a further 10 minutes and then heated to 70 ° C. at a heating rate of 1 ° C./min. After a holding time of 15 minutes at 70 ° C, the temperature is raised to 98 ° C. After 90 minutes of dyeing at 98 ° C., the mixture is cooled to 85 ° C., adjusted to pH 8.5 with ammonia and treated at 85 ° C. for 15 minutes. After cooling to 60 ° C, the liquor is drained.
  • the dark brown colored yarn is rinsed as usual, acidified with 1 kg of 85% formic acid and dried.
  • the coloring is irrelevant and has good fastness properties.
  • the dyeing machine and the material carrier are absolutely clean.
  • the dyeing liquor After adding a solution containing 8 kg of a disazo dye of the formula (22), the dyeing liquor is kept at 50 ° C. for a further 10 minutes and then heated to 70 ° C. at a heating rate of 1 ° C./min. After a holding time of 15 minutes at 70 ° C, the temperature is raised to 98 ° C. After 90 minutes of dyeing at 98 ° C., the mixture is cooled to 85 ° C., adjusted to pH 8.5 with ammonia and treated at 85 ° C. for 15 minutes. After cooling to 60 ° C, the liquor is drained.
  • the blue-black colored fabric is rinsed as usual, acidified with 1 kg of 85% formic acid and dried.
  • the coloring is irrelevant and has good fastness properties.
  • the dyeing machine and the material carrier (perforated tree) are absolutely clean.
  • the dye liquor After adding a solution containing 8 kg of a disazo dye of the formula (22), the dye liquor is kept at 50 ° C. for 10 minutes and then heated to 70 ° C. at a heating rate of 1 ° C./min. After a holding time of 15 minutes at 70 ° C, the temperature is raised to 98 ° C. After 90 minutes of dyeing at 98 ° C., the mixture is cooled to 85 ° C., adjusted to pH 8.5 with ammonia and treated at 85 ° C. for 15 minutes. After cooling to 60 ° C, the liquor is drained.
  • the blue-black colored fabric is rinsed as usual, acidified with 1 kg of 85% formic acid and dried.
  • the coloring is irrelevant and has good fastness properties.
  • the dyeing machine and the material carrier (perforated tree) are absolutely clean.

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Claims (14)

1. Procédé pour teindre des fibres naturelles de polyamide, en particulier de laine, avec des colorants réactifs, d'après le procédé par épuisement, dans lequel la matière fibreuse est soumise d'abord à un traitement préalable, dans un bain, avec un adjuvant de teinture formé d'une combinaison (a) de composés ammonium quaternaire de de polyglycol et (b) d'esters-acides de polyglycol dérivés d'oxyacides au moins bifonctionnels, ou de leurs sels, les composés ammonium quaternaire ainsi que les esters-acides étant dérivés d'une amine aliphatique qui comporte 12 à 24 atomes de carbone dans le reste aliphatique, et en présence (c) d'un éther de polyalcoylèneglycol et d'alcool gras, et ensuite, après addition du colorant, la matière fibreuse est teinte dans le même bain, caractérisé en ce que l'éther de polyalcoylèneglycol et d'alcool gras répond à la formule
Figure imgb0037
 où R représente un reste aliphatique comportant au moins 8 atomes de carbone, "alcoylène" représente un reste éthylène ou propylène, et m vaut de 3 à 25.
2. Procédé selon la revendication 1, caractérisé en ce que R représente un reste alcoyle ou alcényle comportant 12 à 22 atomes de carbone.
3. Procédé selon la revendication 1 ou 2, caractérisé en ce que "alcoylène" représente éthylène.
4. Procédé selon une des revendications 1 à 3, caractérisé en ce que m vaut de 10 à 20.
5. Procédé selon une des revendications 1 à 4, caractérisé en ce que m vaut de 12 à 18.
6. Procédé selon une des revendications 1 à 5, caratérisé en ce que le composant (a) est un composé ammonium quaternaire répondant à la formule
Figure imgb0038
 dans laquelle R₁ représente un reste d'hydrocarbure aliphatique comportant 12 à 22 atomes de carbone, V représente un reste alcoyle éventuellement substitué, l'un des restes Z₁ et Z₂ représente un atome d'hydrogène ou un groupe méthyle ou phényle et l'autre représente un atome d'hydrogène, An⊖ représente un anion d'un acide minéral ou organique, et p et s valent chacun de 1 à 100, la somme de p et s valant de 2 à 100.
7. Procédé selon une des revendications 1 à 6, caractérisé en ce que le composant (b) est un ester-acide, ou un sel de celui-ci, d'un composé répondant à la formule
Figure imgb0039
 ou un produit quaternisé de l'ester-acide ou de son sel, où R₂ représente un reste d'hydrocarbure aliphatique comportant 12 à 22 atomes de carbone, l'un des restes Z₃ et Z₄ représente un atome d'hydrogène ou un groupe méthyle ou phényle et l'autre représente un atome d'hydrogène, et n₁ et n₂ représentent des nombres entiers, la somme n₁+n₂ valant de 2 à 100.
8. Procédé selon une des revendications 1 à 7, caractérisé en ce que les composants (a) et (b) sont présents en un rapport pondéral de 1:3 à 3:1 de l'un à l'autre.
9. Procédé selon une des revendications 1 à 8, caractérisé en ce que le mélange d'adjuvants contient, comme composants (a) et (b),
(Aa) un sel d'ammonium quaternaire répondant à la formule
Figure imgb0040
 et
(Bb) un ester-acide, ou son sel, d'un composé répondant à la formule
Figure imgb0041
 où
X représente un atome d'hydrogène ou SO₃M,
M représente un atome d'hydrogène ou de métal alcalin ou -NH₄,
R₃ et R₄ représentent chacun, indépendamment l'un de l'autre, un groupe alcoyle ou alcényle comportant 12 à 22 atomes de carbone,
V₁ représente un groupe méthyle, éthyle, benzyle, -CH₂CO-NH₂ ou
Figure imgb0042
 (An)₁ représente l'ion chlorure ou méthosulfate, s₁, p₁, n₃ et n₄ sont des nombres entiers, les sommes (p₁+s₁) et (n₃+n₄) valant chacune de 5 à 15.
10. Procédé selon une des revendications 1 à 9, caractérisé en ce que le rapport pondéral du mélange des composants (a) et (b) au composant (c) vaut de 2:1 à 1:1.
11. Procédé selon une des revendications 1 à 10, caractérisé en ce qu'on utilise des colorants réactifs qui contiennent au moins deux groupes acide sulfonique.
12. Procédé selon la revendication 11, caractérisé en ce que les colorants réactifs répondent à la formule
Figure imgb0043
 où
T₁ et T₂ représentent chacun, indépendamment l'un de l'autre, un atome d'hydrogène ou un groupe alcoyle en C₁-C₄, et
Y₁ et Y₂ représentent chacun, indépendamment l'un de l'autre, un groupe chloroacétyle, α -bromoacryloyle, α,β-dibromopropionyle, 2,4-dichloro-s-triazinyle, 2,4-difluoro-5-chloropyrimidine-(6)-yle ou 2,4,5-trichloropyrimidine-(6)-yle.
13. Procédé selon la revendication 12, caractérisé en ce que, dans la formule (7), Y₁ et Y₂ représentent des groupes α-bromoacryloylé ou α,β-dibromopropionyle.
14. Procédé selon la revendication 12,, caractérisé en ce que le colorant réactif répond à la formule
Figure imgb0044
EP88810631A 1987-10-14 1988-09-15 Procédé de teinture de fibres en polyamide naturelles avec des colorants réactifs Expired - Lifetime EP0312493B1 (fr)

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JP (1) JPH01111079A (fr)
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AU (1) AU604353B2 (fr)
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NZ (1) NZ226247A (fr)

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DE59104446D1 (de) * 1990-02-14 1995-03-16 Ciba Geigy Ag Verfahren zum Färben von Wolle mit Reaktivfarbstoffen.
US5230709A (en) * 1990-11-15 1993-07-27 E. I. Du Pont De Nemours And Company Polyamide dyeing process utilizing controlled anionic dye addition
EP0555182B1 (fr) * 1992-02-06 1998-03-04 Ciba SC Holding AG Procédé de teinture de fibres polyamides naturelles ou synthétiques
DE4215589A1 (de) * 1992-05-12 1993-11-18 Bayer Ag Färbeverfahren
DE59610256D1 (de) * 1995-05-18 2003-04-30 Ciba Sc Holding Ag Die Verwendung von Hilfsmittelzubereitungen beim Färben von Wolle
DE19527365A1 (de) * 1995-07-26 1997-01-30 Ciba Geigy Ag Verfahren zum Färben von Wolle mit Reaktivfarbstoffen
KR100363874B1 (ko) * 2000-08-26 2002-12-12 한국생산기술연구원 알파-브로모아크릴아미도-벤젠술폰산 화합물, 그 제조방법및 폴리아마이드섬유의 방염조제로서의 용도
US9863089B2 (en) 2013-03-05 2018-01-09 Nike, Inc. Method for dyeing golf balls and dyed golf balls
US9970155B2 (en) 2013-03-05 2018-05-15 Nike, Inc. Acid dyeing of polyurethane materials

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CH465553A (de) * 1965-09-09 1968-06-14 Ciba Geigy Verfahren zum Färben von stickstoffhaltigen Textilfasern mit Wollfarbstoffen
LU76634A1 (fr) * 1977-01-24 1978-09-13
EP0112797A1 (fr) * 1982-11-26 1984-07-04 Ciba-Geigy Ag Procédé de teinture ou d'impression, avec des colorants réactifs, de matières fibreuses contenant de la cellulose
US4713482A (en) * 1985-03-26 1987-12-15 Ciba-Geigy Corporation Maleic or phthalic acid half esters of alkoxylated fatty amines
US4778919A (en) * 1986-02-25 1988-10-18 Ciba-Geigy Corporation Maleic or phthalic acid half esters of alkoxylated fatty amines

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NZ226247A (en) 1990-03-27
JPH01111079A (ja) 1989-04-27
DE3872824D1 (de) 1992-08-20
AU604353B2 (en) 1990-12-13
AU2241588A (en) 1989-04-20
EP0312493A1 (fr) 1989-04-19
KR890006913A (ko) 1989-06-16

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