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
  • D06P1/44—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
  • D06P1/52—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 synthetic macromolecular substances
  • D06P1/5207—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • D06P1/5214—Polymers of unsaturated compounds containing no COOH groups or functional derivatives thereof
  • D06P1/5242—Polymers of unsaturated N-containing compounds
• • 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
  • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
  • D06P5/02—After-treatment
  • D06P5/04—After-treatment with organic compounds
  • D06P5/08—After-treatment with organic compounds macromolecular
• • 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
  • D06P3/58—Material containing hydroxyl groups
  • D06P3/60—Natural or regenerated cellulose
  • D06P3/62—Natural or regenerated cellulose using direct 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
  • 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
  • D06P3/58—Material containing hydroxyl groups
  • D06P3/60—Natural or regenerated cellulose
  • D06P3/66—Natural or regenerated cellulose 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
  • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
  • D06P5/02—After-treatment
  • D06P5/04—After-treatment with organic compounds
  • D06P5/06—After-treatment with organic compounds containing nitrogen
• • 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
  • Y10S8/918—Cellulose textile

Definitions

• the present invention relates to a method for treating colored cellulose fiber material, in particular colored cellulose fiber material, to improve the fastness properties.
• Dyes and prints with reactive dyes or substantive dyes often show inadequate wet fastness properties, especially wash and water fastness.
• the dye which is bound to the surface of the cellulose, can be removed by repeated washing operations and reapplied to neighboring textile material, which is washed in the same washing cycle.
• This deficiency is generally countered by following the dyeing process with post-treatment with a fixative based on products containing formaldehyde, homo- or copolymers based on (di) allylamine or (poly) amine-dicyandiamide condensates.
• the known fixatives have disadvantages, e.g. a lack of effectiveness or a negative influence on other fastness properties, e.g. lightfastness, or are ecologically questionable. There is therefore a need for improved fixing agents for the treatment of cellulose fiber material dyed with reactive dyes or substantive dyes, which do not have the disadvantages mentioned.
• the groups of the formula (2) can each be present in the homo- or copolymers used according to the invention in the form of the free amine or in salt form, with in principle all common anions, e.g. the sulfate anion or preferably a halide anion such as the bromide or chloride ion.
• the alkyl radical R 1 is, for example, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl or straight-chain pentyl, hexyl, heptyl, octyl, nonyl, decyl, Undecyl or dodecyl, where these alkyl radicals can each carry one or more identical or different of the aforementioned substituents.
• R 1 preferably denotes one optionally substituted C 1 -C 6 -alkyl radical as mentioned above, particularly preferably a C 1 -C 4 -alkyl radical optionally substituted as mentioned above and particularly preferably a C 2 -C 4 -alkyl radical which carries at least one of the aforementioned substituents.
• the alkyl radical R3 is, for example, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl or straight-chain pentyl, hexyl, heptyl or octyl.
• R3 preferably denotes C 1 -C 4 alkyl, particularly preferably methyl or ethyl and particularly preferably methyl.
• Y can be any anion.
• Y - preferably stands for a halide anion, for example for the bromide ion Br - or in particular for the chloride ion Cl - .
• Alk is, for example, methylene or straight-chain or branched ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene or decylene.
• the rest (alk) is preferably straight-chain or branched C 1 -C 6 -alkylene, for example methylene, 1,1 or 1,2-ethylene, 1,2- or 1,3-propylene or straight-chain or branched butylene, pentylene or hexylene, and particularly preferably for C 1 -C 4 alkylene.
• T means, for example, hydrogen, or a radical -NH 2 , -NHR 3 , -N (R 3 ) 2 , -N (R 3 ) 3 + Y - , in which the abovementioned meanings and preferences apply to R 3 and Y - .
• T is preferably hydrogen, amino, N-mono- or N, N-di-C 1 -C 2 -alkylamino or a radical -N (R 3 ) 3 + Y - , where R3 is hydrogen, methyl or ethyl and Y - Halide anion mean.
• TN N-Di-C 1 -C 2 alkylamino or a radical -N (R 3 ) 3 + Y - , in which R 3 is methyl or ethyl and Y is the bromide or chloride anion, is particularly preferred.
• radical R 1 is substituted by aminophenylsulfonyl, it is, for example, o- or m-aminophenylsulfonyl and preferably p-aminophenylsulfonyl.
• R 1 preferably denotes an unsubstituted or by hydroxy, cyano, carbamoyl, a residue -CONH- (alk) -T, N, N-di-C 1 -C 4 alkylcarbamoyl, p-aminophenylsulfonyl, amino or a residue -NHR 3 , -N (R 3 ) 2 , -N (R 3 ) 3 + Y - or -COO- (alk) -T substituted C 1 -C 6 -alkyl radical, where (alk) C 1 -C 4 -alkylene, R 3 C 1 -C 4 alkyl, Y - a halide anion and T hydrogen, amino, Are N-mono- or N, N-di-C 1 -C 4 alkylamino or an N, N, N-tri-C 1 -C 4 alkylammonium halide.
• R 1 preferably represents a C 1 -C 4 -alkyl radical which is unsubstituted or by hydroxy, cyano, amino, N-mono- or N, N-di-C 1 -C 2 -alkylamino, N, N, N-tri -C 1 -C 2 alkylammonium halide or a radical -CONH- (CH 2 ) 1-3 -N (R 3 ) 2 or -COO- (CH 2 ) 1-3 -N (R 3 ) 2 , in which R 3 Means methyl or ethyl, is substituted.
• R 1 are C 1 -C 2 alkyl, especially methyl, hydroxy-C 1 -C 2 alkyl, especially 2-hydroxyethyl, cyano-C 1 -C 3 alkyl, especially 2-cyanoethyl, N, N-Di-C 1 -C 2 alkylamino-C 1 -C 3 alkyl, especially 2-N, N-dimethylaminoethyl or a radical of the formula -CH 2 -CH (OH) - (CH 2 ) n -T, (3a) -CH 2 -CH (R 4 ) -COO- (CH 2 ) m -T, (3b) or -CH 2 -CH (R 4 ) -CONH- (CH 2 ) m -T (3c), wherein R 4 is hydrogen or methyl, n is the number 1 or 2 and m is a number from 1 to 3 and TN, N-di-C 1 -C 2 alkylamin
• radicals R and R 2 have one of the meanings given above for R 1 , the preferences given above apply independently.
• R and R 2 independently of one another each preferably represent hydrogen or C 1 -C 4 alkyl, particularly preferably hydrogen, methyl or ethyl and particularly preferably each hydrogen.
• the homopolymers and copolymers containing recurring structures of the formula (2) given above, used as fixing agents, can be prepared, e.g. by polymerizing N-vinylimidazole and optionally other copolymerizable monomers in a suitable manner and optionally followed by hydrolysis.
• the homopolymers and copolymers used as fixing agents and containing recurring structures of the formulas (1a) and (1b) given above can be prepared, for example by using N-vinylformamide or N-vinylacetamide and, if appropriate, others copolymerizable monomers polymerized, then hydrolyzed and the free amino groups of the homo- or copolymer obtained in an alkylation reaction with an alkyl halide R 1 -X and optionally RX 'and R 2 -X ", where R, R 1 and R 2 each have the meaning given above and X, X 'and X "each independently represent a halide anion, preferably each the bromide or chloride ion.
• the reaction of the amino groups of the homo- or copolymer with a suitable epoxide or with a double bond-containing unsaturated compound is also suitable.
• the homopolymers and copolymers used as fixing agents containing recurring structures of the formulas (1a) and (1b) given above, in which R and R 2 are each hydrogen, can also advantageously be prepared by using a suitable vinylformamido compound, for example of the formula and where R 1 has the meaning given above, polymerized and then hydrolyzed acidic or alkaline.
• the following copolymerizable monomers are suitable, for example: allylamine or diallylamine derivatives such as, for example, diallylamine, N-methyldiallylamine, N-ethyldiallylamine, N, N-dimethyldiallylamonium chloride; Monomers with a carboxyl function, for example (meth) acrylic acid, maleic acid, fumaric acid, itaconic acid, mesaconic acid, citraconic acid, vinyl acetic acid, vinyl oxyacetic acid, vinyl propionic acid, crotonic acid, aconitic acid, allyl acetic acid, allyloxy acetic acid, ⁇ , ⁇ -dimethylacrylic acid, allyl malalonic acid, 2 meth) acrylic acid, 2-halogeno (meth) acrylic acid, ⁇ -ethyl acrylic acid, acrylamidoglycolic acid, glutaconic acid, ⁇ -carboxye
• Preferred copolymerizable monomers in the fixing agents according to the invention are allylamine or diallylamine derivatives, (meth) acrylic acid, maleic acid, N-vinylpyrrolidone, N-vinylformamide, N-vinylacetamide, N-vinyl-N-methylformamide, N-vinyl-N -methyl-acetamide, N-vinyl-N-ethyl-acetamide, N-vinylimidazole, vinyl acetate, vinyl propionate, hydroxy-C 2 -C 4 -alkyl- (meth) acrylate, (meth) acrylic acid-C 1 -C 22 alkyl ester , Acrylonitrile, methacrylonitrile, acrylamide, methacrylamide, N-mono / N, N-di-C 1 -C 10 -alkyl- (meth) acrylamide or N, N-di-C 1 -C 2 -alkylamino-C 2
• copolymerizable monomers in the fixing agents according to the invention are acrylic acid, methacrylic acid, acrylonitrile, methacrylonitrile, N-vinylpyrrolidone, N-vinylformamide, N-vinyl acetamide, N-vinyl imidazole, vinyl acetate, acrylamide, methacrylamide, N-mono- or N, N-di -C 1 -C4 alkyl (meth) acrylamide.
• the homo- or copolymers used as fixatives have an average molecular weight of e.g. ⁇ 500000 and preferably 1000 to 200000.
• the polymers used as fixing agents are produced in a manner known per se, e.g. by ionically or preferably radically initiated polymerization of the corresponding monomers e.g. in solution, suspension or emulsion, and optionally subsequent hydrolysis.
• the polymerization is preferably carried out in solution with a peroxide, persulfate or an azo compound, e.g. with potassium persulfate or azo-bis- (2-amidinopropane) hydrochloride, as radical chain starter, this e.g. is present in an amount of 0.005 to 10 wt .-%, based on the monomers used.
• a hydrolysis step this takes place under alkaline or preferably under acidic conditions. In the case of acidic hydrolysis, predominantly polymers with structural units of the formula (1b) or (2) given above are obtained in salt form.
• the homopolymer or copolymer used according to the invention as a fixing agent is used, for example in an amount of 0.05 to 10% by weight, preferably 0.2 to 4, regardless of the liquor ratio % By weight and particularly preferably 0.8 to 2.5% by weight of active compound, based on the weight of the cellulose fiber material.
• the treatment of the cellulose fiber material with the fixing agent can take place before, during or preferably after dyeing.
• the process according to the invention is advantageously carried out by first dyeing the cellulose fiber material in a customary manner and then post-treating with a fresh aqueous liquor containing the fixing agent in the amount specified above.
• the dyed cellulose fiber material can then be dewatered without further rinsing and dried in the usual way.
• cellulose fiber material comes e.g. regenerated cellulose or especially natural cellulose, e.g. Cellulose, viscose silk, hemp, linen, jute or preferably cotton, as well as fiber blends with synthetic fibers, e.g. Cotton / polyamide, or in particular cotton / polyester mixed fibers.
• natural cellulose e.g. Cellulose, viscose silk, hemp, linen, jute or preferably cotton
• synthetic fibers e.g. Cotton / polyamide, or in particular cotton / polyester mixed fibers.
• the textile can be used in any form, e.g. as a flake, yarn, bobbin, skein, fabric, knitted fabric or felt consisting entirely or partially of native or regenerated cellulose.
• the dyeings are carried out using noun dyes or reactive dyes, all customary direct dyes and reactive dyes, such as those e.g. in Color Index, 3rd edition (1971) and the supplements to it under the rubrics "Direct Dyes” and “Reactive Dyes”.
• Examples are sulfo group-containing monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan or dioxazine dyes which, in the case of reactive dyes, contain at least one fiber-reactive group, e.g. a halotriazinyl group or a vinylsulfonyl group.
• the dyeing of the cellulose fiber material with the dye can be carried out in the customary manner by the exhaust process or by a two-stage process, for example by means of padding or printing and subsequent fixing.
• an exhaust process or padding with subsequent fixing of the dye to the fiber is preferred.
• the fixation can be done in the usual way, e.g. by means of heat according to a steaming process or a thermal insulation process or preferably by the cold dwell method, advantageously by storing the impregnated fiber material at room temperature.
• the aftertreatment is preferably carried out using the exhaust method.
• the liquor ratio can be chosen within a wide range and is e.g. 1: 4 to 1: 100 and preferably 1: 5 to 1:40.
• Special devices are not required.
• the usual dyeing machines e.g. Open baths, reel runners, jiggers or paddles, jet or circulation devices can be used.
• the treatment time can e.g. 20 to 60 minutes and preferably 30 to 40 minutes.
• the pH of the liquor is usually 4 to 8 and preferably 5 to 7.
• the liquor can contain other conventional additives, e.g. Electrolytes such as Sodium chloride or sodium sulfate, dispersing and wetting agents and defoamers.
• Electrolytes such as Sodium chloride or sodium sulfate, dispersing and wetting agents and defoamers.
• the process according to the invention gives dyeings and prints of reactive dyes or substantive dyes on cellulose fiber material which have a considerable improvement in the fastness to wetness, such as, for example, the fastness to washing and water and in particular the fastness to chlorine, without the color yield, shade or light fastness being adversely affected.
• the treated dyeings and prints show no stiffening.
• the polymer solution obtained according to Example 1 is diluted with water to a content of 20% by weight and heated with 40 g of 37% hydrochloric acid at 80 ° C. for 4 hours. A viscous, clear polymer solution is obtained.
• the polymer essentially contains units of the formulas and is available as hydrochloride.
• a solution of 9 g of acrylic acid in 88 g of deionized water is neutralized with approx. 16 g of a 30% sodium hydroxide solution up to pH 6.6.
• This acrylic acid solution, 11.8 g of vinyl imidazole and 13.9 g of vinyl pyrrolidone are placed in a reactor and heated to approx. 80 ° C.
• a solution of 0.85 g of azo-bis (amidinopropane) hydrochloride in 10 g of water is then added dropwise within 90 minutes. Then allowed to polymerize for 4 hours at 80 ° C.
• a polymer solution is obtained, the active substance of which is essentially structural units of the formulas contains.
• a polyvinylamine hydrochloride solution (degree of hydrolysis approx. 80% concentration approx. 18%, produced analogously to US 4,421,602) are placed in a reactor, adjusted to pH 10.5 by adding NaOH and heated to 75.degree.
• a solution of 42.6 g (3-chloro-2-hydroxypropyl) trimethylammonium chloride in 42.6 g of water is added dropwise at 75 ° C. in the course of 60 minutes, and the pH is kept at about 10 in the process. 4 hours at 75-80 ° C, then adjusts the pH to 2.0, the polymer falls into ethanol and dries it.
• a 33% aqueous solution of the polymer is then produced, which essentially has structural units of the formula contains.
• 2 pieces of 20 g of a bleached cotton jersey are dyed with a liquor ratio of 1:30 by a pull-out process by placing the cotton jersey pre-wetted in water in a liquor heated to 40 ° C. containing 0.3 g of dye of the formula and 20 g / l calc. Glauber's salt comes in, the dyeing temperature is raised to 98 ° C at 1 ° C / min, stained for 60 minutes at this temperature, then allowed to cool to 70 ° C, the dyed material is removed and rinsed in running cold water for 5 minutes.
• One of the two dyed cotton jersey pieces is then treated for 30 minutes at 40 ° C. and a liquor ratio of 1:30 with a fresh, aqueous liquor containing 1% by weight, based on the weight of the textile material, of the polymer according to the example 1 (based on 100% active substance) and adjusted to pH 6 with acetic acid.
• the dyeing aftertreated in this way is dewatered and dried without rinsing.
• 20 g of non-mercerized cotton cretonne is, according to a cold residence process, with an aqueous dye liquor containing 30 g / l of the dye of the formula 10 g / l calc.
• the dyed cotton fabric is then treated for 30 minutes at 40 ° C. and a liquor ratio of 1:30 with a fresh aqueous liquor which has 1% by weight, based on the weight of the textile material, of the polymer according to Example 1 (based on to 100% active substance) and adjusted to pH 6 with acetic acid.
• the dyeing aftertreated in this way is dewatered and dried without rinsing.
• the post-treated cotton fabric has a significantly improved wash fastness compared to the non-post-treated cotton fabric.

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• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Coloring (AREA)
• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

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Publications (2)

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• 1997
  • 1997-06-03 EP EP97810340A patent/EP0812949A3/fr not_active Withdrawn
  • 1997-06-06 US US08/870,626 patent/US6039768A/en not_active Expired - Lifetime
  • 1997-06-06 JP JP14948297A patent/JP3963525B2/ja not_active Expired - Fee Related
  • 1997-06-09 CA CA002207424A patent/CA2207424A1/fr not_active Abandoned
  • 1997-06-10 CN CN97112990A patent/CN1114008C/zh not_active Expired - Fee Related

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