EP0342331B1 - Composition poisseuse pour le traitement de matériaux fibreux en polyester - Google Patents

Composition poisseuse pour le traitement de matériaux fibreux en polyester Download PDF

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Publication number
EP0342331B1
EP0342331B1 EP89104695A EP89104695A EP0342331B1 EP 0342331 B1 EP0342331 B1 EP 0342331B1 EP 89104695 A EP89104695 A EP 89104695A EP 89104695 A EP89104695 A EP 89104695A EP 0342331 B1 EP0342331 B1 EP 0342331B1
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Prior art keywords
substituted
alkyl group
unsubstituted
branched
linear
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EP89104695A
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German (de)
English (en)
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EP0342331A2 (fr
EP0342331A3 (fr
Inventor
Wolfgang Becker
Günter Uphues
Uwe Dr. Ploog
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Priority to AT89104695T priority Critical patent/ATE95855T1/de
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
    • D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
    • D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
    • D06M13/295—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof containing polyglycol moieties; containing neopentyl moieties
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions
    • 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
    • Y10S8/04—Polyester fibers

Definitions

  • the invention relates to mixtures which contain oxidized polyethylenes and selected quaternary ammonium phosphates, and to the use of these mixtures as drawable textile auxiliaries for the antistatic, smooth and / or plasticizing of polyester-containing fiber materials.
  • the Aviv für aqueezing is part of the textile finishing and should give the flake, the sliver, woven fabric, knitted fabric or nonwoven in particular such properties as feel, smoothness, antistatic and fullness, through which the appearance, saleability, fitness for purpose and processing properties are increased.
  • the textile auxiliaries used for finishing can, for example, be applied to textile fiber materials in a full bath (exhaust process).
  • the full bath treatment the textiles are wetted for a long time in a large liquor ratio and then dewatered by squeezing, suctioning or centrifuging.
  • the full bath treatment has the advantage that the treatment times and temperatures can be chosen and varied as desired (see, for example, W. Bernard: “Textile finishing", 2nd edition, page 257-258, Springer-Verlag 1967).
  • Fat-polyamine condensation products, fatty acid amide derivatives, paraffin emulsions and silicone derivatives are usually used as antistatic agents, smoothing agents and / or plasticizers in the exhaust process.
  • antistatic agents smoothing agents and / or plasticizers in the exhaust process.
  • polyester-containing fiber materials have no or only unsatisfactory antistatic properties, smoothness and / or softness after finishing with these known substances.
  • the object on which the invention is based was therefore to develop textile auxiliaries which have a high substantivity to polyester-containing fiber materials and which give these fiber materials excellent antistatic smoothing and / or softening properties.
  • blends containing oxidized polyethylenes and certain quaternary ammonium phosphates have a high affinity for polyester-containing fiber materials.
  • the weight ratio of components A: B in the mixtures according to the invention is preferably between 10: 1 and 1: 5, particularly preferably between 10: 3 and 1: 2.
  • mixtures containing anoxidized polyethylenes with average molecular weights between 3000 and 8000, acid numbers between 25 and 60, saponification numbers between 40 and 80 and densities between 0.94 and 1.09 g / cm3 and at least one quaternary ammonium phosphate from at least one of the groups (B) 1-3, as textile auxiliaries for antistatic, smoothing and / or softening polyester-containing fiber materials is therefore also an object of the invention.
  • Anoxidized polyethylenes with average molecular weights between 3500 and 5000 and densities between 0.98 and 1.00 g / cm3 are preferred in the mixtures according to the invention.
  • the mixtures according to the invention which are preferably in the form of dispersions or solutions, particularly preferably in the form of aqueous emulsions, preferably contain between 5 and 50% by weight, particularly preferably between 10 and 30% by weight of components A and B.
  • the dispersions or solutions, preferably aqueous emulsions are applied in a manner known per se in rinsing, washing or immersion baths or by spraying processes on polyester-containing fiber materials and dried between 80 and 160 ° C. by means of spinning, squeezing and temperature treatment.
  • the mixtures according to the invention are preferably applied in the exhaust process from aqueous liquors at liquor ratios between 1: 5 and 1:25 at liquor pH values between 4.0 and 7.0 and temperatures between 40 and 80 ° C. Since textile auxiliaries containing component A and component B according to the invention have a high affinity for polyester-containing fiber materials, a high level of exhaustion of the treatment liquors is achieved.
  • Polyethylene-containing fiber materials include pure polyester fibers and mixtures of polyester fibers and natural and / or synthetic fibers, for example mixtures of polyester fibers and cotton; Polyester fibers and polyamide fibers; Polyester fibers, cotton and polyamide fibers; Polyester fibers and polyacrylic fibers understood.
  • the textile fiber materials are in the form of a flake, sliver, yarn, knitwear, woven fabric or nonwoven, preferably a flake or sliver.
  • the material can be raw white, bleached or colored.
  • the anoxidized polyethylenes contained in the mixtures according to the invention are commercial products which are offered, for example, by Allied Corp., USA under the name A-C® polyethylenes.
  • amines, imidazolines and amino-functional polyesters and phosphoric acid partial esters required as starting materials for the production of quaternary ammonium phosphates can be obtained by processes known from the literature:
  • Amines which can be prepared, for example, by hydrogenation of fatty acid nitriles (Ullmann's Encyclopedia of Industrial Chemistry, Volume 11, pages 448-449, Verlag Chemie, Weinheim 1976) or directly from fatty alcohols and ammonia according to GB-A-1 074 603 are preferred if desired reacted with ethylene oxide and / or propylene oxide at temperatures between 130 and 180 ° C with the proviso that the polyalkyl ether chains of the tertiary amines formed consist of 1 to 5 ethylene oxide and / or propylene oxide units.
  • Cocosamine, oleylamine, tallow amine, cocoalkyl-di-2-hydroxyethyl-amine, dimethyl-laurylamine and N-C12 ⁇ 14-alkylmorpholine are examples of amines which are suitable for the preparation of quaternary ammonium phosphates.
  • An example of acylated amines is cocoylamidopropyldimethylamine.
  • the condensation is carried out at temperatures between 150 and 240 ° C., preferably between 150 and 200 ° C.
  • the molar ratio of carboxylic acid: diamine is preferably between 1: 1 and 1: 2.
  • the carboxylic acids can be used either individually or in a mixture to prepare the imidazolines.
  • fatty acid mixtures such as those that occur when natural fats and / or oils are split. Individual fractions of such fatty acid mixtures are also suitable for the preparation of the imidazolines.
  • the carboxylic acids used are preferably those of the general formula R4-COOH, in which the radical R4 is a straight-chain or branched-chain, substituted or unsubstituted, saturated alkyl group having 7 to 17 carbon atoms or for a straight-chain or branched-chain, substituted or unsubstituted, unsaturated alkyl group having 17 to 21 carbon atoms, for example caprylic acid, capric acid, lauric acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolinic acid, gadoleic acid and / or ricinoleic acid.
  • 1-Hydroxyethyl-2-undecylimidazoline, 1-hydroxyethyl-2-heptadecenylimidazoline and 1-hydroxyethyl-2-heptylimidazoline are suitable imidazolines.
  • alkoxylated tertiary amines required for the production of amino-functional polyesters are derived from primary alkyl and / or alkenylamines, for example from methylamine, ethylamine, butylamine, octylamine, decylamine, dodecylamine, cetylamine, oleylamine, linoleylamine, coconut amine and / or tallow amine. Alkyl amines made from coconut oil or tallow are preferred.
  • Alkyl and / or alkenyl amines are alkoxylated in a manner known per se at from 130 to 180 ° C. with ethylene oxide and / or propylene oxide, with the proviso that the degree of alkoxylation (sum of a and b) is between 2 and 30.
  • Tallow polyester 5 ethylene oxide units (EO) and adipic acid, polyester from coconut amine. 2 EO and adipic acid, polyester from coconut amine. 5 EO and succinic acid and / or polyester from tallow amine. 10 EO and sebacic acid are examples of suitable amino-functional polyesters.
  • the phosphoric acid partial esters are prepared from straight-chain or branched-chain, saturated or unsaturated, substituted or unsubstituted, optionally alkoxylated alcohols having 6 to 22 carbon atoms.
  • Straight or branched chain, substituted or unsubstituted, saturated, optionally alkoxylated alcohols having 8 to 18 C atoms and / or straight or branched chain, substituted or unsubstituted, unsaturated, optionally alkoxylated alcohols having 18 to 22 C atoms are used, for example 2-ethylhexanol, n-octanol, isononyl alcohol, decyl alcohol, dodecyl alcohol, isotridecyl alcohol, tetradecyl alcohol, hexadecyl alcohol, octadecyl alcohol, octadecenyl alcohol, eicosenyl alcohol, docosenyl alcohol.
  • alcohols are optionally reacted with 1 to 10 moles of ethylene oxide, propylene oxide and / or butylene oxide.
  • the optionally alkoxylated alcohols are phosphated in a manner known per se by reacting 3 mol of alcohol with 1 mol of phosphorus pentoxide at 50 to 80 ° C.
  • water is treated at 90 to 100 ° C. for several hours.
  • the mixtures according to the invention are used as textile auxiliaries for the antistatic, smoothing and / or softening of polyester-containing fiber materials, these mixtures are preferably in the form of dispersions or solutions, particularly preferably in the form of aqueous emulsions. These emulsions contain 2 to 20% by weight of nonionic, cationic and / or amphoteric dispersants.
  • Suitable nonionic dispersants are alkoxylated, preferably ethoxylated and / or propoxylated fats, oils, fatty alcohols with 8 to 24 carbon atoms in the fat residue, fatty amines with 8 to 24 carbon atoms in the fat residue and / or C8 ⁇ 18 alkylphenols, for example ethoxylated castor oil, Oleyl alcohol. 5 EO, omelet acetyl alcohol. 5 EO, tallow alcohol. 14 EO, stearylamine. 2 EO, tallow amine. 2 EO, stearylamine. 10 EO and / or nonylphenol. 10 EO.
  • Suitable cationic dispersants are alkoxylated, preferably ethoxylated and / or propoxylated, alkylamines having 10 to 20 carbon atoms in the form of their ammonium salts, for example stearylamine. 10 EO.
  • Suitable amphoteric dispersants are, for example, C8 ⁇ 22-alkyldimethylbetaines, N-C8 ⁇ 22-alkylamidobetaines and / or amphoteric surfactants derived from amino acids.
  • the solutions or dispersions can contain further smoothing agents, for example paraffins with softening points between 35 and 80 ° C, fatty acid esters with 12 to 24 C atoms both in the fatty acid residue and in the straight and / or branched chain, saturated and / or unsaturated alcohol residue such as isotridecyl stearate, stearyl stearate and / or behenyl behenate and / or silicones such as dimethylpolysiloxane, plasticizers such as fatty acid amidopolyamines and / or quaternary ammonium salts, for example dimethyldistearylammonium chloride, antioxidants, for example oxygen acids of phosphorus and / or alkali metal sulfides and carboxylic acids, for example C-regulating agents and / or contain C1 ⁇ 4-hydroxycarboxylic acids such as acetic acid and / or glycolic acid.
  • paraffins with softening points between 35 and 80 ° C saturated and
  • the proportion of optional components in aqueous dispersions and emulsions is between 2 and 20% by weight.
  • the dispersions and solutions, preferably the aqueous emulsions, which contain the mixtures according to the invention, are prepared in a manner known per se by mixing anoxidized polyethylenes, dispersants and optional constituents with water and stirring them in a pressure-resistant apparatus at from 130 to 170.degree. After cooling, finely divided, storage-stable emulsions are obtained, into which quaternary ammonium phosphates and optionally further dispersants are stirred.
  • the mixtures according to the invention are heat-resistant and do not cause discoloration of the fiber materials.
  • the polyester-containing fiber materials finished with the mixtures according to the invention show, in comparison to untreated, only with anoxidized polyethylene or only with quaternary Ammonium phosphates treated polyester-containing fiber materials significantly reduced anti-electrostatic charges, low static and dynamic fiber / fiber and fiber / metal friction, excellent smoothness and good soft feel.
  • the conveyor belts produced on the needle bar section were assessed according to the cohesion meter measuring method.
  • the measured values cN. tex ⁇ 1 represent the 1.25-fold forces that are required to change the length of the original material.
  • the measured values determined were processed statistically using a Rothschild F-Meter with the aid of a connected small computer.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Woven Fabrics (AREA)
  • Yarns And Mechanical Finishing Of Yarns Or Ropes (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
  • Chemical Treatment Of Fibers During Manufacturing Processes (AREA)
  • Materials For Medical Uses (AREA)

Claims (9)

  1. Mélanges contenant
    A) des polyéthylénes partiellement oxydés ayant un poids moléculaire moyen entre 3000 et 8000, des indices d'acide entre 25 et 60, des indices de saponification entre 40 et 80 et une densité entre 0,94 et 1,09 g/cm³ et
    B) au moins un phosphate d'ammonium quaternaire choisi dans au moins un des groupes suivants :
    1.)
    Figure imgb0038
     dans lesquels
    R¹   signifie un radical alcoyle ayant de 6 à 22 atomes de carbone, substitué ou non substitué, à chaîne droite ou ramifiée, saturé ou non saturé.
    R²   signifie
    Figure imgb0039
     méthyle ou éthyle
    R³   signifie
    Figure imgb0040
     méthyle, éthyle ou bien
    R² et R³   ensemble signifient -CH₂CH₂-O-CH₂CH₂
    R⁴   signifie un radical alcoyle ayant de 5 à 21 atomes de carbone, substitué ou non substitué, à chaîne droite ou ramifiée, saturé ou non saturé.
    R⁵   signifie de l'hydrogène ou un radical alcoyle ayant de 1 à 4 atomes de carbone.
    R   signifie un radical alcoyle ayant de 6 à 22 atomes de carbone, substitué ou non substitué, à chaîne droite ou ramifiée saturé ou non saturé et
    A   signifie une chaîne alcoylène de 2 à 4 atomes de carbone.
    p   est 2 ou 3 et
    n   = 1, m = 2 ou bien n = 2, m = 1
    2.)
    Figure imgb0041
     dans lesquels
    R⁴   signifie un radical alcoyle ayant de 5 à 21 atomes de carbone, substitué ou non substitué, à chaîne droite ou ramifiée, saturé ou non saturé.
    R⁶   signifie OH ou
    R   signifie un radical alcoyle ayant de 6 à 22 atomes de carbone, substitué ou non substitué, en chaîne droite ou ramifiée, saturé ou non saturé et
    A   signifie une chaîne alcoylène ayant de 2 à 4 atomes de carbone et
    n   = 1, m = 2 ou n = 2, m = 1
    3.) des phosphates d'ammonium quaternaire à base de polyesters aminofonctionnels, avec des degrés de polymérisation compris entre 2 et 50, produits par condensation d'acides dicarboxyliques de formule générale :



            HOOC-R⁷ -COOH



    dans laquelle
    R⁷   signifie un reste substitué ou non substitué, aliphatique, alicyclique ou aromatique ayant de 1 à 10 atomes de carbone,
    avec des amines tertiaires alcoxylées de formule générale :
    Figure imgb0043
     dans laquelle
    R⁸   signifie un radical alcoyle ayant de 1 à 20 atomes de carbone, substitué ou non substitué, à chaîne droite ou ramifiée, saturé ou non saturé et
    A'   signifie un groupe éthylène et/ou isopropylène
    a et b   sont des nombres entre 1 et 20 avec la restriction que la somme a + b s'élève de 2 à 30
    mise en réaction avec des mono et/ou des dialcoylesters d'acide phosphorique de formules générales :
    Figure imgb0044
     et
    Figure imgb0045
     dans lesquelles
    R   signifie un radical alcoyle ayant de 6 à 22 atomes de carbone, substitué ou non substitué, à chaîne droite ou ramifiée, saturé ou non saturé et
    A   signifie une chaîne alcoylène ayant de 2 à 4 atomes de carbone
    en présence d'eau à 50 - 80°C et
    réaction subséquente avec des oxydes d'alcoylène ayant de 2 à 4 atomes de carbone à des pressions comprises entre 1 et 5 bar, et à des températures entre 80 et 100°C avec la restriction, que la chaîne de l'étherpolyalcoylé des fonctions amine quaternaire est composée de 1 à 10 unités d'oxyde d'alcoylène.
  2. Mélanges selon la revendication 1, caractérisés en ce que le rapport pondéral des composants A : B se situe de préférence entre 10 : 1 et 1 : 5, de préférence entre 10 : 3 et 1 : 2.
  3. Mélanges selon l'une ou les deux revendications 1 à 2, caractérisés en ce que les polyéthylènes partiellement oxydés, possédent un poids moléculaire moyen compris entre 3500 et 5000 et une densité entre 0,98 et 1,00 g/cm³.
  4. Mélanges selon l'une ou plusieurs des revendications 1 à 3, caractérisés en ce que dans les formules générales pour le composant B 1) à 3), R¹ signifie un radical alcoyle ayant de 8 à 18 atomes de carbone, substitué ou non substitué, une chaîne droite ou ramifiée, saturé un radical alcoyle ayant de 18 à 22 atomes de carbone, substitué ou non substitué, en chaîne droite ou ramifiée, non saturé, ou bien
    Figure imgb0046
    R⁴   signifie un radical alcoyle ayant de 7 à 17 atomes de carbone, substitué ou non substitué, en chaîne droite ou ramifiée, saturé ou bien un radical alcoyle ayant de 17 à 21 atomes de carbone, substitué ou non substitué, en chaîne droite ou ramifiée, non saturé.
    A   signifie des groupes éthylène et/ou isopropylène
    R⁶   signifie OH
    R⁸   signifie un radical alcoyle ayant de 6 à 20 atomes de carbone, substitué ou non substitué, à chaîne droite ou ramifiée, saturé ou non saturé et
    R   signifie un radical alcoyle ayant de 8 à 18 atomes de carbone, saturé, en chaîne droite ou ramifiée, substitué ou non substitué ou bien un radical alcoyle ayant de 18 à 22 atomes de carbone non saturé, en chaîne droite ou ramifiée, substitué ou non substitué.
  5. Mélanges selon l'une ou plusieurs des revendications 1 à 4, caractérisés en ce que ceux-ci se présentent sous forme de solutions ou de dispersions, de préférence sous forme d'émulsions aqueuses.
  6. Mélanges selon la revendication 5, caractérisés en ce que la teneur des composants A et B dans des émulsions aqueuses se situe entre 5 et 50 % en poids, de préférence entre 10 et 30 % en poids.
  7. Mélanges selon l'une ou les deux revendications 5 à 6, caractérisés en ce que les émulsions renferment de 2 à 20 % en poids d'agents dispersants non ioniques, cationiques et/ou amphotères.
  8. Mélanges selon l'une ou plusieurs des revendications 5 à 7, caractérisés en ce que les mélanges contiennent des graisses, des huiles ou des alcools gras alcoxylés ayant de 8 à 24 atomes de carbone dans le reste gras, des amines grasses ayant de 8 à 24 atomes de carbone dans le reste gras et/ou des alcoylphénols avec 8 à 18 atomes de carbone.
  9. Utilisation des mélanges contenant le composant A et le composant B selon une ou plusieurs des revendications 1 à 8 comme adjuvant du textile en vue de l'action antistatique, du lissage et/ou de l'assouplissement de matériaux fibreux contenant des polyesters.
EP89104695A 1988-03-24 1989-03-16 Composition poisseuse pour le traitement de matériaux fibreux en polyester Expired - Lifetime EP0342331B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT89104695T ATE95855T1 (de) 1988-03-24 1989-03-16 Ziehfaehige zusammensetzung fuer die behandlung von polyesterhaltigen fasermaterialien.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3809928A DE3809928A1 (de) 1988-03-24 1988-03-24 Ziehfaehige textilhilfsmittel fuer polyesterhaltige fasermaterialien
DE3809928 1988-03-24

Publications (3)

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EP0342331A2 EP0342331A2 (fr) 1989-11-23
EP0342331A3 EP0342331A3 (fr) 1991-11-21
EP0342331B1 true EP0342331B1 (fr) 1993-10-13

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US (1) US4975091A (fr)
EP (1) EP0342331B1 (fr)
JP (1) JPH01314783A (fr)
AT (1) ATE95855T1 (fr)
AU (1) AU614045B2 (fr)
BR (1) BR8901358A (fr)
DE (2) DE3809928A1 (fr)
ES (1) ES2059597T3 (fr)

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WO2002079364A1 (fr) * 2001-03-30 2002-10-10 Ciba Specialty Chemicals Holding Inc. Compositions d'adoucissant et leur utilisation

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JPS61289182A (ja) * 1985-06-14 1986-12-19 竹本油脂株式会社 合成繊維用帯電防止剤
DE3618944A1 (de) * 1986-06-05 1987-12-10 Henkel Kgaa Quartaere 2-alkylimidazoliniumsalze, verfahren zu deren herstellung und deren verwendung
US4698391A (en) * 1986-07-30 1987-10-06 Eastman Kodak Company Crosslinked polymers with lowered resistivity and materials and methods for their preparation

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ES2059597T3 (es) 1994-11-16
ATE95855T1 (de) 1993-10-15
JPH01314783A (ja) 1989-12-19
US4975091A (en) 1990-12-04
BR8901358A (pt) 1989-11-07
EP0342331A2 (fr) 1989-11-23
AU3170289A (en) 1989-09-28
AU614045B2 (en) 1991-08-15
DE3809928A1 (de) 1989-10-05
EP0342331A3 (fr) 1991-11-21
DE58905875D1 (de) 1993-11-18

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