EP0625184B1 - Procede de fabrication de concentres aqueux, de faible viscosite, d'esters quaternises - Google Patents

Procede de fabrication de concentres aqueux, de faible viscosite, d'esters quaternises Download PDF

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Publication number
EP0625184B1
EP0625184B1 EP93917366A EP93917366A EP0625184B1 EP 0625184 B1 EP0625184 B1 EP 0625184B1 EP 93917366 A EP93917366 A EP 93917366A EP 93917366 A EP93917366 A EP 93917366A EP 0625184 B1 EP0625184 B1 EP 0625184B1
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Prior art keywords
fatty acid
quaternized
carbon atoms
viscosity
viscosity regulators
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EP93917366A
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EP0625184A1 (fr
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Oriol Ponsati
Joaquim Bigorra
Nuria Bonastre
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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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
    • 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
    • D06M13/322—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 nitrogen
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D06M13/467—Compounds containing quaternary nitrogen atoms derived from polyamines
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/645—Mixtures of compounds all of which are cationic
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C11D3/0015—Softening compositions liquid
    • 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
    • D06M13/10—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 oxygen
    • D06M13/144—Alcohols; Metal alcoholates
    • 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
    • D06M13/10—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 oxygen
    • D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
    • 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
    • D06M13/322—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 nitrogen
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
    • 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

Definitions

  • the invention relates to a process for the preparation of low-viscosity aqueous ester quat concentrates, in which aqueous solutions of quaternized di-fatty acid trialkanolamine ester salts are mixed with selected viscosity regulators.
  • US Pat. No. 2,340,881 describes aqueous dispersions of condensation products made from a hydroxyalkyl polyamine and a fatty acid glyceride. which improve the lubricity and softness of the textiles treated with it.
  • Esterquats are not only distinguished by their excellent softening and antistatic properties, but also have a surprisingly good biodegradability for cationic surfactants. It is disadvantageous, however, that aqueous esterquat concentrates behave dilutantly at low shear forces and are structurally viscous only when shear is strong. In practice, this means that the viscosity of aqueous ester quat concentrates increases by leaps and bounds when pumping and conveying these products through pipelines is therefore extremely problematic.
  • EP-A2 0165138 it is proposed to regulate the viscosity of ester quats based on triethanolamine by adding organic salts such as sodium gluconate or short-chain quaternary ammonium compounds.
  • organic salts such as sodium gluconate or short-chain quaternary ammonium compounds.
  • the reduction in viscosity that can be achieved with this method when pumping is by no means sufficient for the majority of technical applications.
  • WO 88/10294 Use of long-term quaternary ammonium compounds proposed.
  • the object of the invention was therefore to develop a new process for the production of low-viscosity textile treatment agents which is free from the disadvantages described.
  • Quaternized di-fatty acid trialkanolamine ester salts are known substances which are accessible by the relevant methods of preparative organic chemistry. They are usually prepared from fatty acids which are esterified in the first step with trialkanolamines, such as triethanolamine, tripropanolamine or triisopropanolamine. The difatty acid ester formed can then be quaternized in a manner known per se, for example with methyl chloride or dimethyl sulfate.
  • concentration includes 12 to 40, preferably 15 to 25% by weight solutions of the ester quat base in water and the term “ester quat base” 70 to 95, preferably 80 to 90,% by weight. Understand% solutions of the ester quats in isopropyl alcohol.
  • Typical examples of the fatty acid components of these compounds are caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachic acid and behenic acid as well as their technical mixtures, such as are obtained, for example, in the splitting of vegetable oils or animal fats.
  • Textile treatment agents with particularly low viscosity under shear can be prepared by using quaternized di-fatty acid trialkanolamine ester salts of the formula (I) in which R1CO is an acyl radical having 12 to 18 carbon atoms, Z is an ethylene group and / or X is chloride or methosulfate stands.
  • R1CO is an acyl radical having 12 to 18 carbon atoms
  • Z is an ethylene group
  • / or X is chloride or methosulfate stands.
  • Suitable viscosity regulators a) are quaternized unsaturated di-fatty acid trialkanolamine ester salts which follow the formula (II) in the R2CO for an aliphatic, linear or branched acyl radical having 16 to 22 carbon atoms and 1, 2 or 3 double bonds, [Z] for an ethylene, propylene or isopropylene group and X represents chloride, bromide, sulfate, methosulfate or phosphate.
  • unsaturated fatty acids for example palmoleic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, gadoleic acid and / or erucic acid, and their technical mixtures, which in the first stage are mixed with trialkanolamines, such as ethanolamine, propanolamine or isopropanolamine be implemented.
  • the resulting difatty acid esters can then be quaternized in a manner known per se, for example with methyl chloride or dimethyl sulfate.
  • Preferred viscosity regulators are quaternized unsaturated di-fatty acid trialkanolamine ester salts of the formula (II) , the fatty acid components of which are derived from oleic acid and / or elaidic acid.
  • Quaternized or pseudoquaternized fatty acid amidoamines of the formula (IIIa) , (IIIb) and / or (IIIc ) can be used as the viscosity-regulating component b), in the R3CO for an aliphatic, linear or branched acyl radical having 6 to 22 carbon atoms and 0, 1, 2 or 3 double bonds, [Z] for an ethylene, propylene or isopropylene group and X for chloride, bromide, sulfate, methosulfate or phosphate.
  • These substances are also known compounds which can be obtained by esterifying fatty acids with diamines, for example ethylene or propylene diamine, dimethylamine methylamine (DAMA), dimethylamine ethylamine (DAEA) or dimethylamine propylamine (DAPA) and subsequent methylation.
  • diamines for example ethylene or propylene diamine, dimethylamine methylamine (DAMA), dimethylamine ethylamine (DAEA) or dimethylamine propylamine (DAPA) and subsequent methylation.
  • DAMA dimethylamine methylamine
  • DAEA dimethylamine ethylamine
  • DAPA dimethylamine propylamine
  • the components (IIIa) , (IIIb) and (IIIc) can be present side by side in a mixture, the weight ratio within the mixing triangle being 1: 1: 8; 1: 8: 1 and 8: 1: 1 may vary.
  • quaternized fatty acid amidoamines of the formulas (IIIa) , (IIIb) and / or (IIIc) the fatty acid components of which have 12 to 18 and in particular 12 to 14 or 16 to 18 carbon atoms.
  • Quaternized fatty acid amidoamines whose fatty acid components are derived from oleic acid and / or elaidic acid are also particularly preferred.
  • diquaternized fatty acid trialkanolamine ester salts of the formula (IV) are suitable as viscosity-regulating component c), in which R4CO stands for an aliphatic, linear or branched acyl radical with 12 to 18 carbon atoms, [Z] for an ethylene, propylene or isopropylene group and [Y] for an alkylene group with 0 or 1 to 18 carbon atoms.
  • R4CO stands for an aliphatic, linear or branched acyl radical with 12 to 18 carbon atoms
  • [Z] for an ethylene, propylene or isopropylene group
  • [Y] for an alkylene group with 0 or 1 to 18 carbon atoms.
  • the viscosity regulators can be added to the aqueous esterquat concentrates in amounts of 0.1 to 10, preferably 1 to 8 and in particular 3 to 7% by weight, based on the 100% by weight di-fatty acid trialkanoamine salt.
  • the mixing can take place mechanically, for example by stirring or dispersing; a chemical reaction does not take place.
  • aqueous esterquat concentrates obtainable by the process according to the invention are low-viscosity, easily pumpable even with short-term, low shear and have excellent anti-static and anti-static properties. They are therefore suitable for the production of textile treatment agents, in which they can be present in amounts of 5 to 95, preferably 10 to 90% by weight, based on the composition.
  • test mixtures were optionally tempered to 20 ° C. after adding the viscosity regulators and pumped in a circle over a period of 30 min using a peristaltic pump (Heidolph RZR2, 800 rpm). Before the pumping tests were carried out and after they had ended, the viscosities of the mixtures were determined using a Brookfield RVT viscometer (spindle 2 to 7.10 rpm). The results are summarized in Table 1 (percentages as% by weight). Table 1 Viscosity measurements in the pump test E.g.
  • EQ ester quat
  • test mixtures were optionally added to a homogenizer of the rotor-stator mixer type after the addition of the viscosity regulators, and were mixed there at 20 ° C. initially five times for 5 minutes and finally once for 15 minutes.
  • the viscosities of the mixtures were determined before the start and after the end of each mixing period using the Brookfield method (see pump test). The results are summarized in Table 2 (percentages as% by weight) Table 2 Viscosity measurements in the homogenizer test E.g.

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  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Textile Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Des concentrés aqueux, de faible viscosité, d'esters quaternisés sont obtenus en mélangeant des solutions aqueuses de sels de trialcanolamine-esters de diacides gras quaternisés, de formule (I) dans laquelle R1CO désigne un reste acyle saturé aliphatique, linéaire ou ramifié, de 6 à 22 atomes de carbone, [Z] désigne un groupe éthylène, propylène ou isopropylène, et X désigne un chorure, un bromure, un sulfate, méthosulfate ou phosphate, avec au moins un régulateur de viscosité choisi dans le groupe comprenant a) des sels de trialcanolamine-esters de diacides gras insaturés quaternisés, b) des sels d'amido-amines d'acides gras quaternisés, c) des composés d'ammonium quaternaire à chaînes longues, et, d) des sels de triéthanolamine-esters d'acides gras di-quaternisés.

Claims (12)

  1. Procédé de fabrication de concentrés aqueux, de faible viscosité, d'esters quaternisés, caractérisé en ce que l'on mélange des solutions aqueuses de sels de diesters quaternisés de trialcanolamine et d'acide gras de la formule (I)
    Figure imgb0016
     dans laquelle R¹CO représente un radical acyle saturé aliphatique, linéaire ou ramifié, comportant 6 a 22 atomes de carbone, [Z] correspond a un groupe éthylène, propylène ou isopropylène et X est un chlorure, un bromure, un sulfate, un méthosulfate ou un phosphate,
    avec au moins un régulateur de viscosité, qui est sélectionné dans le groupe constitué des
    (a) sels de diesters quaternisés de trialcanolamine et d'acide gras insaturé,
    (b) sels quaternisés ou pseudoquaternisés d'amidoamine et d'acide gras et des
    (c) sels diquaternisés d'esters de trialcanolamine et d'acide gras.
  2. Procédé selon la revendication 1, caractérisé en ce que l'on met en oeuvre comme esters quaternisés, des sels de diesters quaternisés de trialcanolamine et d'acide gras de la formule (I), dans laquelle R¹CO représente un radical acyle comportant 12 à 18 atomes de carbone, Z correspond à un groupe éthylène et/ou X est un chlorure ou un méthosulfate.
  3. Procédé selon une des revendications 1 et 2, caractérisé en ce que l'on met en oeuvre comme régulateurs de viscosité, des sels de diesters quaternisés de trialcanolamine et d'acide gras insaturé de la formule (II),
    Figure imgb0017
     dans laquelle R²CO représente un radical acyle aliphatique, linéaire ou ramifié, comportant 16 à 22 atomes de carbone et 1, 2 ou 3 doubles liaisons, [Z] correspond à un groupe éthylène, propylène ou isopropylène et X est un chlorure, un bromure, un sulfate, un méthosulfate ou un phosphate.
  4. Procédé selon la revendication 3, caractérisé en ce que l'on met en oeuvre comme régulateurs de viscosité, des sels de diesters quaternisés de trialcanolamine et d'acide gras insaturé de la formule (II), dont les composants acide gras sont dérivés des acides oléique et/ou élaïdique.
  5. Procédé selon les revendications 1 et 2, caractérisé en ce que l'on met en oeuvre comme régulateurs de viscosité, des amidoamines d'acides gras quaternisées ou pseudoquaternisées de la formule (IIIa), (IIIb) et/ou (IIIc),
    Figure imgb0018
    Figure imgb0019
     dans lesquelles R³CO représente un radical acyle aliphatique, linéaire ou ramifié, comportant 6 à 22 atomes de carbone et 0, 1, 2 ou 3 doubles liaisons, [Z] correspond à un groupe éthylène, propylène ou isopropylène et X est un chlorure, un bromure, un sulfate, un méthosulfate ou un phosphate.
  6. Procédé selon la revendication 5, caractérisé en ce que l'on met en oeuvre comme régulateurs de viscosité, des amidoamines quaternisées d'acides gras des formules (IIIa), (IIIb) et/ou (IIIc), dont les composants acide gras comportent 12 à 18 atomes de carbone.
  7. Procédé selon la revendication 5, caractérisé en ce que l'on met en oeuvre comme régulateurs de viscosité, des amidoamines quaternisées d'acides gras des formules (IIIa), (IIIb) et/ou (IIIc), dont les composants acide gras comportent 12 à 14 atomes de carbone.
  8. Procédé selon la revendication 5, caractérisé en ce que l'on met en oeuvre comme régulateurs de viscosité, des amidoamines quaternisées d'acides gras des formules (IIIa), (IIIb) et/ou (IIIc), dont les composants acide gras comportent 16 à 18 atomes de carbone.
  9. Procédé selon la revendication 5, caractérisé en ce que l'on met en oeuvre comme régulateurs de viscosité, des amidoamines quaternisées d'acides gras des formules (IIIa), (IIIb) et/ou (IIIc), dont les composants acide gras sont dérivés des acides oléique et/ou élaïdique.
  10. Procédé selon les revendications 1 et 2, caractérisé en ce que l'on met en oeuvre comme régulateurs de viscosité, des sels d'esters diquaternisés de triéthanolamine et d'acide gras de la formule (IV),
    Figure imgb0020
     dans laquelle R⁴CO représente un radical acyle aliphatique, linéaire ou ramifié, comportant 12 à 18 atomes de carbone, [Z] correspond à un groupe éthylène, propylène ou isopropylène et [Y] est un groupe alkylène possédant 0 ou 1 à 18 atomes de carbone.
  11. Procédé selon la revendication 10, caractérisé en ce que l'on met en oeuvre des régulateurs de viscosité de la formule (IV), dans laquelle R⁴CO représente un radical acyle comportant 16 à 18 atomes de carbone, [Y] correspond à un groupe alkylène possédant 4 à 8 atomes de carbone et [Z] est un groupe éthylène.
  12. Procédé selon les revendications 1 à 11, caractérisé en ce que l'on ajoute les régulateurs de viscosité aux concentrés aqueux d'esters quaternisés en proportions de 0,1 à 10 % en poids, par rapport au sel de diester de trialcanolamine et d'acide gras à 100 % en poids.
EP93917366A 1992-02-07 1993-01-29 Procede de fabrication de concentres aqueux, de faible viscosite, d'esters quaternises Expired - Lifetime EP0625184B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19924203489 DE4203489A1 (de) 1992-02-07 1992-02-07 Verfahren zur herstellung niedrigviskoser waessriger esterquat-konzentrate
DE4203489 1992-02-07
PCT/EP1993/000203 WO1993016157A1 (fr) 1992-02-07 1993-01-29 Procede de fabrication de concentres aqueux, de faible viscosite, d'esters quaternises

Publications (2)

Publication Number Publication Date
EP0625184A1 EP0625184A1 (fr) 1994-11-23
EP0625184B1 true EP0625184B1 (fr) 1995-12-20

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EP (1) EP0625184B1 (fr)
JP (1) JPH07503503A (fr)
DE (2) DE4203489A1 (fr)
ES (1) ES2081719T3 (fr)
WO (1) WO1993016157A1 (fr)

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CA2134640C (fr) * 1992-05-12 1998-11-03 Ellen Schmidt Baker Compositions concentrees d'assouplissants pour tissus contenant des assouplissants biodegradables
DE4243550C1 (de) * 1992-12-22 1994-06-01 Henkel Kgaa Faserhilfsmittel und deren Verwendung
DE4324395A1 (de) * 1993-07-21 1995-01-26 Henkel Kgaa Verfahren zur Herstellung von Weichspüler-Dispersionen
EP0648835A1 (fr) * 1993-10-14 1995-04-19 The Procter & Gamble Company Utilisation de sels alcalins de polyammonium pour augmenter la densité cationique des adoussinants textiles
BR9408310A (pt) * 1993-12-13 1997-08-26 Procter & Gamble Composição de amaciamento de tecido concentrada líquida de viscosidade estável
DE4402527A1 (de) * 1994-01-28 1995-08-03 Henkel Kgaa Wäßrige Lösungen von Esterquats
DE4405702A1 (de) * 1994-02-23 1995-08-24 Witco Surfactants Gmbh Hochkonzentrierte wäßrige Weichspülmittel mit verbesserter Lagerstabilität
DE4435386A1 (de) * 1994-10-04 1996-04-11 Henkel Kgaa Wäßrige Weichspülerdispersionen
DE19649285A1 (de) 1996-11-28 1998-06-04 Henkel Kgaa Verfahren zum Schutz von Metalloberflächen gegenüber Korrosion in flüssigen oder gasförmigen Medien
WO1999064661A1 (fr) * 1998-06-11 1999-12-16 Kao Corporation Composition adoucissante
US6211140B1 (en) * 1999-07-26 2001-04-03 The Procter & Gamble Company Cationic charge boosting systems
DE19962874A1 (de) * 1999-12-24 2001-06-28 Cognis Deutschland Gmbh Transparente Avivagemittel
CA2609058A1 (fr) * 2005-05-18 2006-11-23 Stepan Company Compositions contenant des agents adoucissants, a faible teneur en solides et a haute viscosite destinees aux textiles et leur procede de production
EP2082805A1 (fr) * 2008-01-28 2009-07-29 Basf Se Procédé pour la préparation d'une suspension colloïdale aqueuse de métaux précieux
CN111051485A (zh) * 2017-09-06 2020-04-21 赢创运营有限公司 特别用于生产织物柔软剂配制物的包含季铵化合物的微乳剂
ES2939182T3 (es) 2017-09-25 2023-04-19 Evonik Operations Gmbh Concentrados estables al almacenamiento que contienen polisiloxanos y su empleo, preferentemente en composiciones de mantenimiento textil
EP3818137B1 (fr) 2018-07-05 2022-11-09 Evonik Operations GmbH Substances actives pour formulations de lavage et de nettoyage fortement visqueuses

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ATE4334T1 (de) * 1979-01-11 1983-08-15 The Procter & Gamble Company Konzentrierte textilweichmachungszusammensetzung.
DE3170187D1 (en) * 1980-11-18 1985-05-30 Procter & Gamble Concentrated fabric softening compositions
DE3588115T3 (de) * 1984-05-16 2003-03-27 Stepan Europe, Voreppe Konzentrierte Weichmacherzusammensetzungen auf der Basis von quaternären ammoniumhaltigen kationischen oberflächenaktiven Verbindungen
GB2188653A (en) * 1986-04-02 1987-10-07 Procter & Gamble Biodegradable fabric softeners
EP0288515B1 (fr) * 1986-10-24 1993-05-05 Isp Investments Inc. Composes quaternises contenant de l'azote
AU623859B2 (en) * 1987-06-16 1992-05-28 Cotelle S.A. Concentrated softening compositions

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DE4203489A1 (de) 1993-08-12
JPH07503503A (ja) 1995-04-13
EP0625184A1 (fr) 1994-11-23
WO1993016157A1 (fr) 1993-08-19
ES2081719T3 (es) 1996-03-16
DE59301215D1 (de) 1996-02-01

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