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EP0342439B1 - Procédé de posttraitement de matériaux textiles teints - Google Patents

Procédé de posttraitement de matériaux textiles teints Download PDF

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Publication number
EP0342439B1
EP0342439B1 EP89108065A EP89108065A EP0342439B1 EP 0342439 B1 EP0342439 B1 EP 0342439B1 EP 89108065 A EP89108065 A EP 89108065A EP 89108065 A EP89108065 A EP 89108065A EP 0342439 B1 EP0342439 B1 EP 0342439B1
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EP
European Patent Office
Prior art keywords
parts
process according
groups
polyurethanes
bis
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP89108065A
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German (de)
English (en)
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EP0342439A2 (fr
EP0342439A3 (fr
Inventor
Udo Winfried Dr. Hendricks
Josef Dr. Sanders
Ergun Dipl.-Ing. Tamer
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Bayer AG
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Bayer AG
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Publication of EP0342439A3 publication Critical patent/EP0342439A3/fr
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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
    • D06P1/44—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
    • D06P1/5264—Macromolecular compounds obtained otherwise than by reactions involving only unsaturated carbon-to-carbon bonds
    • D06P1/5285—Polyurethanes; Polyurea; Polyguanides
    • 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
    • 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
    • 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
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/924—Polyamide fiber

Definitions

  • the invention relates to a process for the aftertreatment of textile materials dyed with anionic dyes from natural and synthetic polyamides with polyurethanes containing quaternary ammonium groups.
  • Printed or dyed textile materials made from natural or synthetic polyamides often have insufficient fastness to washing, especially at higher temperatures, since the bound dye is partially dissolved during washing.
  • Japanese patent application 62-212 412 describes the use of dispersed or dissolved tertiary ammonium groups and blocked isocyanate groups-containing polyurethanes for the treatment of fiber materials.
  • the polyurethanes are soluble or dispersible in water.
  • Examples of compounds of the general formula (I) are N-methyl-diethanolamine, N-methyl-bis- (2-hydroxypropyl) -amine, N-ethyl-diethanolamine, N-butyldiethanolamine, N-butyl-bis- (2-hydroxypropyl) ) -amine, N-octadecyldiethanolamine, N-butyl-bis- (2-hydroxylbutyl) -amine, N-butyl-bis- (3-hydroxy-2-butyl) -amine, N, N-bis- (2-hydroxyethyl ) -cyclohexylamine, N, N-bis- (2-hydroxypropyl) -cyclohexylamine, N-benzyl-diethanolamine, N-benzyl-bis- (2-hydroxypropyl) -amine, N, N-bis- (hydroxyethyl) - and N , N-bis- (2'-hydroxypropyl) -1-amino-3-d
  • Examples of the compounds of the general formula (II) are N, N'-bis (2-hydroxyethyl) piperazine, N, N'-bis (2-hydroxypropyl) piperazine, N, N'-bis (2 -hydroxybutyl- ⁇ ) -piperazine and their reaction products with ethylene oxide and / or propylene oxide.
  • the compounds (I) can also be reacted with the polyisocyanates in a mixture with other compounds D) which are known in polyurethane chemistry and have at least two zerewitinoffactive hydrogen atoms.
  • these mixing components D) are known, inter alia, from DE-A-28 32 253, pages 11 to 20. They have molecular weights between about 60 to 10,000. In addition to compounds containing amino, thiol and / or carboxyl groups, this is preferably taken to mean hydroxyl groups, in particular compounds having 2 to 8 hydroxyl groups and having molecular weights between 800 and 6000. For example, 2 to 4 hydroxyl groups are polyesters , Polyethers, polythioethers, polyacetals, polycarbonates and polyesteramides, as are known per se for the production of homogeneous or cellular polyurethanes.
  • polyethers which are obtained by adding one or more alkylene oxides (ethylene oxide and especially propylene oxide) to divalent or polyvalent "starters” (eg propylene glycol, glycerol, sorbitol, formose or trimethylolpropane), and polyethers which are polyaddition products made from diisocyanates Hydrazine and / or diamines and / or glycols or polymers and / or graft polymers, preferably of styrene and acrylonitrile, in dispersed or dissolved form.
  • polyesters including polycarbonates, as are usually used as a soft segment.
  • the preferred compounds of this type have melting points below 60, preferably below 45 ° C. Compounds containing hydroxyl groups with a functionality of 2 are preferred.
  • this is preferably understood to mean compounds with molecular weights between 60 and 400 which have at least two hydroxyl groups and / or amino groups and / or thiol groups and / or carboxyl groups and / or hydrazide groups and are known as chain extenders or crosslinking agents. These compounds generally have 2 to 8, preferably 2 to 4, hydrogen atoms which are reactive toward isocyanates.
  • Examples include ethylene glycol, 1,4-butanediol, 2,2-dimethylpropanediol, trimethylolpropane, hydrazine, ethylenediamine, 3,3'-dimethyl-4,4'-diaminodicyclohexylmethane, 3,5-diethyl-2,4 (and / or 2,6) -diaminotoluene or adipic acid dihydrazide or their mixtures.
  • Chain terminators E) can also be used in the reaction of A) with B).
  • all monofunctional, preferably relatively low molecular weight (molecular weight up to 400) compounds with an NCO-reactive group e.g. Monoalcohols such as methanol, n-octanol, isopropanol, isooctyl alcohol or stearyl alcohol; primary or secondary monoamines such as ethylamine, di-n-butylamine, di-isopropylamine, stearylamine, 4-amino-2,2,6,6-tetramethylpiperidine, acethydrazide, stearyl hydrazide, aniline or thiol compounds such as octyl mercaptan.
  • Monoalcohols such as methanol, n-octanol, isopropanol, isooctyl alcohol or stearyl alcohol
  • primary or secondary monoamines such as ethylamine, di-n-butylamine, di-isopropylamine,
  • Monofunctional compounds having tertiary amino groups are particularly preferred.
  • Examples include 1-amino-2-diethylaminoethane, 1-amino-3-dimethylaminopropane, 1-amino-3-diethylaminopropane, 4-amino-1-diethylaminopentane, furthermore 2- (dimethylamino) -ethanol, 2-diethylaminoethanol, 2- Dibutylaminoethanol, N-methyl-N- (2-dimethylaminoethyl) ethanolamine, N-methyl-N- (3-dimethylaminopropyl) ethanolamine, N-methyl-N- (2-dimethylaminoethoxyethyl) ethanolamine, N- (2-hydroxyethyl ) -2-aza-bicyclo (2,2,1) -heptane, N, N-bis- (3-dimethylaminopropyl) -N- (2-hydroxyethyl) -amine and their reaction products
  • Suitable starting components B) are aliphatic, cycloaliphatic, araliphatic and aromatic polyisocyanates as described, for example, by W. Siefken in Justus Liebigs Annalen der Chemie, 562, pages 75 to 136. Aliphatic diisocyanates are preferred.
  • isocyanatomethane, -ethane, -propane, -butane, -pentane, -hexane, 6-chlorohexyl isocyanate, stearyl isocyanate or benzyl isocyanate and mixtures of these isocyanates are suitable.
  • the starting components A) and B) and, if appropriate, starting components D) and E) which are also used are generally known, in one-stage or multi-stage processes, while maintaining an equivalent ratio from isocyanate groups to isocyanate-reactive groups from 0.8: 1 to 1: 1 at temperatures from 20 to 150 ° C, preferably 50 to 100 ° C, in the absence or in the presence of inert solvents such as benzene, chlorobenzene, toluene, acetone, methyl ethyl ketone , Ethyl acetate, tetrahydrofuran, dioxane, dimethylformamide, dimethyl sulfoxide or N-methyl-pyrrolidone reacted.
  • inert solvents such as benzene, chlorobenzene, toluene, acetone, methyl ethyl ketone , Ethyl acetate, tetrahydrofuran, dioxane, dimethylformamide,
  • Aids and additives of a conventional type e.g. Water, catalysts, surface-active additives, reaction retarders, plasticizers or fungistatic or bacteriostatic substances, stabilizers and light stabilizers can also be used.
  • quaternizing agents preferably those which introduce an optionally substituted C1-C4-alkyl radical or a C7-C9-aralkyl radical into the molecule, at temperatures from 30 ° to 120 ° C, preferably 40 ° to 80 ° C, optionally with the use of solvents such as alcohols, ketones or ethers, for example Methanol, ethanol, isopropanol, acetone, acetonitrile, tetrahydrofuran.
  • solvents such as alcohols, ketones or ethers, for example Methanol, ethanol, isopropanol, acetone, acetonitrile, tetrahydrofuran.
  • quaternizing agents are methyl chloride, methyl bromide, dimethyl sulfate, diethyl sulfate, benzyl chloride, ethylene chlorohydrin, p-toluenesulfonic acid ester, chloroacetic ester and epichlorohydrin.
  • Tertiary nitrogen atoms can also be converted into a cationic charge state which enables solubility or dispersion in water by protonation.
  • these include, for example, inorganic acids such as chlorine, bromine and hydrogen iodide, perchloric, perbromo, sulfuric and phosphoric acids as well as organic acids such as formic, acetic, mono-, di- and trichloroacetic, propionic, lactic , Methanesulfonic, benzenesulfonic or toluenesulfonic acid into consideration.
  • the proportions are chosen so that 0.5 to 10 equivalents, preferably 0.7 to 1.0 equivalents, of the quaternizing agent are used per tertiary amino group.
  • the tertiary amino groups not converted into quaternary ammonium groups are then preferably neutralized by adding one of the above-mentioned inorganic or organic acids.
  • the textile materials used for the aftertreatment can be wool, silk and synthetic polyamides such as polymers of ⁇ -caprolactam and polymers of dicarboxylic acid and diamines, for example of adipic acid and hexamethylene diamine.
  • the textile materials can be in the form of flake, sliver, yarn or piece goods.
  • the aftertreatment method is preferred of dyed wool applied. This can be unchlorinated or chlorinated wool or finished with a synthetic resin pretreatment. Particularly good effects are obtained in the aftertreatment of dyeings on chlorinated wool or treated with felt-free synthetic resin.
  • the chlorination of the wool can be carried out continuously or discontinuously with hypochlorous acid or with chloroisocyanurate using the customary method.
  • the felt-free finishing can be done by various known methods, e.g. according to the HERCOSETT process. These processes, also known as superwashing equipment, are chlorination processes and processes in which the fiber is coated with a resin, e.g. a polyurethane, polyacrylic, melamine / polyalkyleneimine / epichlorohydrin or polyamide / epichlorohydrin resin is treated.
  • a resin e.g. a polyurethane, polyacrylic, melamine / polyalkyleneimine / epichlorohydrin or polyamide / epichlorohydrin resin is treated.
  • the polyurethanes suitable according to the invention are preferably added to the aftertreatment baths in the form of aqueous solutions, the amounts of the polyurethanes being able to vary within wide limits.
  • the aftertreatment of the textile material is expediently carried out in such a way that the dyed material, preferably wool which has already been treated free of felt, is introduced into an aqueous liquor which contains the condensation products suitable according to the invention and has a pH between 6 and 10.
  • the liquor is added by adding alkaline compounds e.g. Ammonia or soda, adjusted to pH 8-10.
  • the temperature of the treatment bath is raised to 50 ° to 80 ° C. in the course of 20 to 30 minutes and left for 5 to 30 minutes.
  • the material is then rinsed with cold water, acidified with acetic acid, dewatered and dried.
  • the aftertreatment can be carried out by the exhaust process or else continuously or semi-continuously by padding or spraying with subsequent exposure to heat.
  • polyurethanes with quaternary ammonium groups which are suitable according to the invention can be increased from case to case by the use of nonionic, cationic or amphoteric, surface-active substances.
  • nonionic, cationic or amphoteric, surface-active substances are, for example, ethylene and / or propylene oxide adducts of fatty amines can be quaternized and / or sulfated. They are known to the person skilled in the art as a leveling agent for wool dyes.
  • the amount of such products used is 50 to 100%, preferably 70 to 80%, of the amount of the condensation products according to the invention.
  • the fastness properties of the dyed textile materials in particular the wet fastness properties, such as the sweat fastness according to IWS-TM 174 (test method for alkaline sweat fastness) and the wash fastness according to IWS-TM 193 (test method for fastness to washing) are considerably improved with the aid of the method according to the invention, without the rubbing rights being adversely affected.
  • the dyes used are the dyes usually used for dyeing fibers containing polyamide groups, e.g. Acid dyes, metal complex dyes, which can contain water-solubilizing groups such as sulfonic acid or carboxylic acid groups or also sulfonamide or alkylsulfone residues, and reactive dyes. They are described in more detail in the Color Index. Dyes of this type, which otherwise have good fastness properties, result in few real colors on keratin-containing materials which have been treated with felt-free materials, particularly in the case of deep shades.
  • reaction mixture was diluted with 100 parts of acetone and 50 parts of dimethyl sulfate were added dropwise at 40 to 45 ° C. The mixture was then stirred at 40 to 45 ° C for 30 minutes and at 50 to 60 ° C for 2 hours.
  • reaction mixture 261 parts were at 40 to 45 ° C. mixed with 66 parts of dimethyl sulfate. The mixture was then diluted with 150 parts of water and stirred at 40 to 45 ° C. for 2 hours. After distilling off the acetone in a water jet vacuum, the residue was dissolved in 225 parts of 1-methoxy-propanol-2 and 213 parts of water.
  • reaction mixture 208 parts were diluted with 100 parts of acetone and 50 parts of dimethyl sulfate were added at 40 to 50 ° C. After 30 minutes, 200 parts of water were added and the mixture was stirred at 50 to 60 ° C. for 2 hours.
  • reaction mixture 224 parts were diluted with 100 parts of acetone and 49 parts of dimethyl sulfate were added at 40 to 50 ° C. After stirring for 30 minutes at 40 to 50 ° C., the mixture was diluted with 200 ml of water and stirred at 50 to 60 ° C. for a further 2 hours.
  • Yarns made of wool which have been treated with Hercosett 57 "Superwash” chlorination and treatment with an adipic acid / diethylenetriamine-epichlorohydrin reaction product
  • a dye liquor which is in liters 1.0 g of the dye CI Acid Bue 49 (No. 62 095) 2.0 g sodium sulfate calc. 1.5 g acetic acid (40%) 0.5 g of the leveling aid of the formula contains.
  • the dyebath is heated to boiling within 60 minutes and dyed at this temperature for 60 minutes.
  • the dyeing is then rinsed and after-treated at 50 ° C. for 30 minutes with a liquor which is in liters 1.6 g of the reaction product according to Example 1 and 4.0 g sodium sulfate calc. contains and is adjusted to pH 7.5 to 8.0 with ammonia solution, with no bleeding of the color.
  • the dyeing is rinsed, acidified with acetic acid, dehydrated and dried.
  • the HERCOSETT-finished wool yarns are dyed as described in Example 14 and then treated at 50 ° C. for 30 minutes with a liquor in liters 2.0 g of the reaction product according to Example 8 and 4.0 g sodium sulfate calc. contains and is adjusted to pH 7.5 to 8.0 with ammonia solution, with no bleeding of the color. The dyeing is then rinsed, acidified with acetic acid, dehydrated and dried.
  • the dye liquor is then heated to boiling within 30 minutes and held at this temperature for 60 minutes. After rinsing, the dyeing is aftertreated at 50 ° C for 30 minutes with a liquor in liters 2.5 g of the reaction product according to Example 2 and 4.0 g sodium sulfate calc.
  • the aftertreatment is carried out as described in Example 14.
  • the dyeing obtained in this way has very good fastness properties, this is done without worsening the rub fastness.
  • Wool yarn skeins equipped with HERCOSETT 57 are placed at room temperature in a 1:25 liquor ratio in a dye liquor, in liters 1.2 g of the red dye of FR-PS 1 389 345, Example 1 2.0 g sodium sulfate calc. 2.0 g acetic acid (60%) 0.4 g of an auxiliary mixture consisting of 50 parts of the reaction product from 1 mol of N-methyl-stearylamine and 20 mol of EO and 50 parts of the reaction product from 1 mol of N-ethyl-stearylamine and 35 mol of EO contains. Both dyeing and aftertreatment are carried out as described in Example 14, but with the difference that the aftertreatment is carried out with 1.2 g of the reaction product according to Example 4 carries out.
  • Wool comb which was previously chlorinated as usual, is dyed in a liquor ratio of 1:10 as described in Example 14 and after-rinsed in a liquor at 50 ° C. for 5 minutes, which 4.8 g of the reaction product according to Example 12 contains.
  • the pH of the treatment bath is then adjusted to approximately 7.5 to 8.0 by adding ammonia solution.
  • the dyeing is treated at 50 ° C for a further 25 minutes.
  • the ridge is then rinsed, acidified with acetic acid, dewatered and dried.
  • the aftertreatment is carried out as described in Example 14, but with the difference that the aftertreatment is carried out with 3.2 g of the reaction product according to Example 11 carries out.
  • the dyeing obtained in this way has very good fastness properties; this happens without deterioration in rubbing fastness.
  • the dye liquor is then heated to boiling within 60 minutes and kept at this temperature for 60 minutes. After rinsing, the dyeing is aftertreated at 50 ° C for 30 minutes with a liquor in liters 3.5 g of the reaction product according to Example 13 contains and is adjusted to pH 7.5 to 8.0 with ammonia solution, with no bleeding of the color.
  • the dyeing is then rinsed, acidified with acetic acid, dehydrated and dried.
  • the dyeing has a significantly higher level of fastness than that of the non-post-treated dyeing; this happens without deterioration in rubbing fastness.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Coloring (AREA)

Claims (10)

  1. Procédé pour le traitement complémentaire de matières textiles en polyamides teintes par des colorants anioniques par des polyuréthannes contenant des groupes ammonium quaternaires.
  2. Procédé selon la revendication 1, caractérisé en ce que les polyuréthannes sont obtenus par réaction de
    A) des composés contenant des groupes amino tertiaires et au moins deux groupes hydroxy,
    avec
    B) des polyisocyanates
    et
    C) des agents quaternisants.
  3. Procédé selon la revendication 2, caractérisé en ce que, à la préparation des polyurétyannes, on utilise en tant que composant A) des hydroxyalkylamines de formules générales
    Figure imgb0014
     ou
    Figure imgb0015
     dans lesquelles
    Q¹ et Q² représentent chacun, indépendamment l'un de l'autre, un groupe de formule générale
    Figure imgb0016
     A représente un groupe alkyle en C₁-C₁₈, cycloalkyle en C₅-C₈, aralkyle en C₇-C₉ ou un groupe de formule
    Figure imgb0017
     ou



            HO-Q¹-R¹-



    R¹, R² et R⁴ représentent chacun, indépendamment les uns des autres, un groupe alkylène en C₂-C₆, cycloalkylène en C₅-C₈ ou aralkylène en C₇-C₉,
    R³ représente l'hydrogène ou un groupe méthyle,
    R⁵ représente un groupe alkyle en C₁-C₁₈, cycloalkyle en C₅-C₈, aralkyle en C₇-C₉ ou un groupe de formule



            HO-Q¹-R¹-



    et
    m, n et r sont des nombres allant de 0 à 30.
  4. Procédé selon la revendication 2, caractérisé en ce que, à la préparation des polyuréthannes, on utilise en tant que composant B), des polyisocyanates aliphatiques, cycloaliphatiques, araliphatiques ou aromatiques, en particulier des diisocyanates aliphatiques.
  5. Procédé selon la revendication 2, caractérisé en ce que le composant A) est mis en oeuvre en mélange avec d'autres composés D), usuels dans la chimie des polyuréthannes, contenant au moins deux atomes d'hydrogène actifs selon Zerewitinoff.
  6. Procédé selon la revendication 2, caractérisé en ce que l'on fait réagir A) et B) en présence de coupeurs de chaîne E).
  7. Procédé selon la revendication 2, caractérisé en ce que l'on fait réagir A) et B) et le cas échéant D) et/ou E) en maintenant un rapport de 0,8:1 à 1:1 entre les équivalents de groupes isocyanate et les équivalents de groupes réactifs avec les groupe isocyanate, à des températures de 20 à 150°C.
  8. Procédé selon la revendication 2, caractérisé en ce que, à la quaternisation, on fait réagir de 0,7 à 1,0 équivalent d'agent quaternisant par groupe amino tertiaire du produit d'addition et le cas échéant on protonise les groupes amino tertiaires restants par traitement à l'aide d'acides.
  9. Procédé selon la revendication 1, caractérisé en ce que le polyamide soumis au traitement est la laine.
  10. Procédé selon la revendication 1, caractérisé en ce que le polyamide soumis au traitement est de la laine ayant subi un apprêtage antifeutrant.
EP89108065A 1988-05-17 1989-05-04 Procédé de posttraitement de matériaux textiles teints Expired - Lifetime EP0342439B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3816699 1988-05-17
DE3816699A DE3816699A1 (de) 1988-05-17 1988-05-17 Verfahren zur nachbehandlung von gefaerbten textilmaterialien

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EP0342439A2 EP0342439A2 (fr) 1989-11-23
EP0342439A3 EP0342439A3 (fr) 1991-09-18
EP0342439B1 true EP0342439B1 (fr) 1994-01-19

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US5714802A (en) * 1991-06-18 1998-02-03 Micron Technology, Inc. High-density electronic module
GB9202375D0 (en) * 1992-02-05 1992-03-18 Ici Plc Process
US6136433A (en) * 1997-05-01 2000-10-24 Basf Corporation Spinning and stability of solution-dyed nylon fibers
DE10060048A1 (de) * 2000-12-01 2002-06-06 Bayer Ag Filzfrei ausgerüstete Wolle und Verfahren zur Filzfreiausrüstung
US20100261813A1 (en) * 2007-03-21 2010-10-14 Barrett Richard Bobsein Thickener composition and method for thickening aqueous systems
US9970155B2 (en) 2013-03-05 2018-05-15 Nike, Inc. Acid dyeing of polyurethane materials
US9863089B2 (en) * 2013-03-05 2018-01-09 Nike, Inc. Method for dyeing golf balls and dyed golf balls
CN107217518B (zh) * 2017-07-24 2019-06-07 北京泛博化学股份有限公司 一种耐汗渍牢固提升剂及其制备方法、应用
CN116556063B (zh) * 2022-09-01 2025-03-07 广东德美精细化工集团股份有限公司 一种水性自润滑湿摩擦牢度提升剂及其制备方法

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GB1547958A (en) * 1975-03-06 1979-07-04 Iws Nominee Co Ltd Amphoteric polymers and process for their use
US4098772A (en) * 1976-03-11 1978-07-04 The Upjohn Company Thermoplastic polyurethanes prepared with small amounts of monohydric alcohols
DE2626495A1 (de) * 1976-06-12 1977-12-29 Bayer Ag Quartaere reaktivverbindungen
DE2747358C2 (de) * 1977-10-21 1986-12-04 Bayer Ag, 5090 Leverkusen Verfahren zur Nachbehandlung von Reaktivfärbungen
JPS54151689A (en) * 1978-05-17 1979-11-29 Dai Ichi Kogyo Seiyaku Co Ltd Improving of abrasion fastness
CH665325GA3 (fr) * 1981-02-13 1988-05-13
IT1198254B (it) * 1986-12-24 1988-12-21 Raffineria Olii Lubirificanti Procedimento per migliorare la tingibilita' di manufatti tessili tessuti o non tessuti

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Publication number Publication date
DE3816699A1 (de) 1989-11-30
EP0342439A2 (fr) 1989-11-23
US4964875A (en) 1990-10-23
EP0342439A3 (fr) 1991-09-18
DE58906730D1 (de) 1994-03-03

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