EP1497402B1 - Compositions d'adoucissant textile contenant des derives d'ester de betaine et procede d'amelioration du pouvoir lavant de lessives - Google Patents

Compositions d'adoucissant textile contenant des derives d'ester de betaine et procede d'amelioration du pouvoir lavant de lessives Download PDF

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Publication number
EP1497402B1
EP1497402B1 EP03718759A EP03718759A EP1497402B1 EP 1497402 B1 EP1497402 B1 EP 1497402B1 EP 03718759 A EP03718759 A EP 03718759A EP 03718759 A EP03718759 A EP 03718759A EP 1497402 B1 EP1497402 B1 EP 1497402B1
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Prior art keywords
radical
fabric softener
washing
rinse cycle
atoms
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Expired - Lifetime
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EP03718759A
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German (de)
English (en)
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EP1497402A1 (fr
Inventor
Michael Fender
Jörg Simpelkamp
Philipp Tomuschat
Bernd Weyershausen
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Evonik Goldschmidt Rewo GmbH
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Goldschmidt Rewo GmbH
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Classifications

    • 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
    • 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
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/94—Mixtures with anionic, cationic or non-ionic 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
    • C11D1/62—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
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/90—Betaines

Definitions

  • the invention relates to fabric softener formulations comprising hydrolyzable betaine ester derivatives in addition to liquid esterquat fabric softener formulations for the controlled release of surfactants and to a commercial process for improving the washing performance of detergents using the fabric softener formulations.
  • wetting of the material to be cleaned with the wash liquor and the wetting of the solid or oily particle dirt are required for a cleaning.
  • Wetting and wetting are effected by surfactants, surfactants.
  • the electrochemical double layer formed between fiber, debris and surfactant is substantially increased by anionic surfactants and builders, thereby enhancing the repellency between soil and fiber.
  • the detached liquid oil and grease dirt is solubilized by the micelles formed by the surfactants and thus kept in the wash liquor.
  • Particle dirt is electrically charged by adsorption of surfactants and dispersed as a result of the repulsion of the individual particles in the wash liquor, so that a redeposition on the fabric is omitted.
  • Nonionic surfactants are generally used in detergent formulations because of their ability to remove greasy and oily soils.
  • Prior art cationic surfactants used in detergent formulations especially because of their attributed additional textilnostinden effects and not exclusively as a cleaning agent.
  • Such additional effects to be observed depending on the structure of the cationic surfactants are, for example, the softening (U.S. 3,607,763), the antistatic (U.S. 3,951,879, U.S. 3,959,157), the bacteriocides (U.S. 2,742,434 US 3 539 520, US 3 965 026) and the color-protecting effect or also the improvement of the water-absorption capacity of the fabrics treated with them.
  • basic detergent formulations are known in which selected nonionic and cationic surfactants are combined to achieve improved soil removal, as described in US Pat. Nos. 4,239,660 and 4,260,529.
  • US Pat. No. 4,260,529 describes laundry detergent formulations containing betaine ester derivatives in the form of cationic ammonium salts in addition to a biodegradable nonionic surfactant.
  • These laundry detergent formulations for the main wash cycle are said to have a high washing effect if they are used in the alkaline wash temperature range of specifically below 11 in the main wash cycle, so that hydrolysis of the surfactants used is prevented.
  • Cationic surfactants of different structure are used as raw materials for laundry softeners. Particularly widespread are Estertagen based on triethanolamine such as N-methyl, N, N-bis (beta-C 14-18 -acyloxyethyl) -, N-beta-hydroxyethylammoniummethosulfat that (under trade names such Tetranyl ® AT 75 trademarks of KAO Corp. .), Stepanex ® VRH 90 (trademark of Stepan Corp.) or Rewoquat ® WE 18 (trademark of Goldschmidt Rewo GmbH & Co. KG) are distributed.
  • Estertagen based on triethanolamine such as N-methyl, N, N-bis (beta-C 14-18 -acyloxyethyl) -, N-beta-hydroxyethylammoniummethosulfat that (under trade names such Tetranyl ® AT 75 trademarks of KAO Corp. .), Stepanex ® VRH 90 (trademark of Step
  • U.S. 4,370,272 discloses alkoxylated quaternary ammonium betaine ester surfactants and their use as hair conditioners or fabric softeners. As advantages, their self-emulsifying action in water and the possibility to dispense with additional nonionic surfactants to obtain a stable emulsion are called. However, the softness of laundry treated with such fabric softeners does not meet the standards achieved by modern esterquat fabric softeners.
  • a disadvantage of the prior art is further that the previously available surfactant molecules have no or no sufficient substantivity to raise from the aqueous liquor onto the fibers, which applies in particular to nonionic surfactant molecules.
  • the object of the present invention was therefore to provide fabric softener formulations which show a significant detergency enhancing effect in the next wash and at the same time meet the standards of modern esterquat softener formulations, in particular with respect to the softening effect, the antistatic effect or the water absorbency of the fabrics treated therewith.
  • the components of the laundry softener formulations must be applied to the textiles (substantivity).
  • the radical R a of the betaine ester derivatives preferably comprises a long-chain alkyl radical having 9 to 17 C atoms.
  • Y according to the formula (II) is a substituted nitrogen atom or phosphorus atom, and the radicals R b and R c are simultaneously -CH 3 .
  • radicals R d and R e may be H at the same time.
  • X is -C (O) -NH- or C (O) -N (CH 3 ) -.
  • R f is preferably an ethylene radical or a propylene radical.
  • Y should preferably be a substituted nitrogen atom according to formula (II).
  • R g is the residue of a fatty alcohol based on natural fatty acids which can be prepared by known processes.
  • fatty acids for the preparation of fatty alcohols are - individually or in mixtures - fatty acids such as caproic, caprylic, capric, 2-ethylhexanoic, lauric, myristic, palmitic, palmitoleic, isostearic, stearic, hydroxystearic (ricinoleic), dihydroxystearic, oleic, linoleic, petroleum , Elaidic acid, arachidic acid, behenic acid and erucic acid, gadoleic acid and the technical mixtures obtained in the pressure splitting of natural fats and oils such as oleic acid, linoleic acid, linolenic acid, and especially coconut oil fatty acid, rapeseed oil fatty acid, soybean oil fatty acid, sunflower oil fatty acid, tall oil fatty acid. In principle, all fatty acids with a similar chain distribution are suitable.
  • the iodine number is the amount of iodine absorbed by 100 g of the compound to saturate the double bonds.
  • the laundry softener formulations mentioned are particularly suitable for achieving the effect according to the invention if they are further characterized in that the betaine ester derivative is stable to hydrolysis at pH values below 3.5 (at temperatures up to 70 ° C.) and in the aqueous alkaline range from pH 8 to 14, in particular 9 to 11 spontaneously to form cationic, anionic, zwitterionic and / or nonionic surfactants to form at least one good fat-soluble surfactant having an HLB value of ⁇ 10, and at least one readily water-soluble surfactant having an HLB value of> 10 is hydrolyzed.
  • the fabric softener formulations have a content of at least 1% by weight, especially 1 to 10, especially 2 to 5, of at least one of the said betaine ester derivatives, together 5 to 20% by weight, especially 13 to 20, of one or more esterquaternary ester derivatives.
  • Softeners, and the rest up to 100 wt .-% of conventional auxiliaries or additives and optionally water.
  • the auxiliaries and additives are preferably selected from nonionic and ionic dispersants, (C 1 to C 5 ) -alkanols, ethylene glycol, propylene glycol, polyglycol, and derivatives thereof, ethoxylated or propoxylated phenol, benzyl alcohol, isopropanol, isobutanol having a mean degree of alkoxylation of> 2.5 to 3.5 and dyes and perfume oils and in particular in a proportion of together up to 5 wt .-%, especially 1 to 3 included.
  • nonionic and ionic dispersants C 1 to C 5 ) -alkanols, ethylene glycol, propylene glycol, polyglycol, and derivatives thereof, ethoxylated or propoxylated phenol, benzyl alcohol, isopropanol, isobutanol having a mean degree of alkoxylation of> 2.5 to 3.5 and dyes and perfume oils and in particular in a proportion of together up
  • the fabric softener formulations of the present invention contain betaine ester derivatives having excellent substantivity, and thus, once grown on the fiber, can be considered to carry an ionic and nonionic surfactant which controls them, that is, releases them at the next wash cycle. In this way, for the first time nonionic surfactants for the subsequent wash cycle by the temporary incorporation into a cationic compound can be fixed on textile fibers.
  • one or more further quaternary ammonium compounds may be present in the laundry softeners according to the invention.
  • a post-treatment of the clean laundry according to step (B) a post-treatment can be carried out exclusively with Betainesterformultechniken alone.
  • the subsequent washing process is carried out analogously (C).
  • the adjustment of the required pH values is carried out by a neutralization step with sufficient amounts of inorganic, but preferably conventional organic mono- or polybasic acids. It is also advantageous Applications of fabric softener formulations the use of corresponding buffer substances instead of acids.
  • a wash usually involves placing the dry or wet soiled laundry in the washing machine and cleaning it with the added detergent and washing mechanics.
  • the usual state-of-the-art detergents wet the dirt located on the textile fibers exclusively from the outside. There are initially no surfactant molecules between the textile fibers and the dirt particles.
  • the soft touch was checked on commercial cotton terry fabric.
  • aqueous fabric softener strength prepared with the additives according to the formulas 2 to 11 is generally in the amount of 2 wt .-% based on the finished fabric softener, in the case of the formulations 3 and 6 in the amount of 5%, were included in the case of the formulations 4 and 7 in the amount of 9 wt .-%.
  • formulations according to the invention with the additions of the betaine ester derivatives Ia-f should ideally have a neutral behavior with respect to the softness of the treated tissue. A negative effect on the softness led to a devaluation in the overall assessment.
  • the use concentration of all fabric softening formulations was 0.025% by weight for softness evaluation.
  • Table 1 formulation softness Recipe 1 4 Recipe 2 3.9 Recipe 3 3.2 Recipe 4 2.7 Recipe 5 3.9 Recipe 6 3.3 Recipe 7 2.6 Recipe 8 3.8 Recipe 9 3.7 Recipe 10 3.8 Recipe 11 3.7 3% recipe 4 1.4 5% recipe 4 1.6
  • the fabric softeners were dosed both with the usual concentration of 0.025 wt .-% active content as well as with an excessive concentration of 0.075 wt .-%.
  • Stainmonitors contain on a piece of fabric 16 different types of dirt, so that a fairly comprehensive evaluation of the washing performance, or stain removal is possible.
  • the washing tests were carried out in Miele W 715 and W 918 washing machines.
  • Table 2 Powder detergent (batch 1) pollution no fabric softener * Formulation 1 * 0.025% by weight Formulation 2 ++ 0.025% by weight Formulation 2 ++ 0.075 wt .-% Make up 59.3 58.0 62.5 57.2 curry 81.7 84.3 89.8 92.0 red wine 63.9 61.4 66.9 61.8 Spaghetti sauce 87.9 84.8 91.9 96.5 dessert 74.7 75.6 75.8 80.0 peat 61.0 58.4 65.4 61.2 tea 56.8 54.8 62.2 66.9 Beta-carotene 72.1 77.6 75.0 90.0 grass 89.0 60.1 91.7 95.1 animal.

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

Claims (11)

  1. Formulations assouplissantes pour le linge contenant des dérivés d'ester de bétaïne de formule générale (I) suivante :
    Figure imgb0008
     dans laquelle
    Y représente selon la formule (II)
    Figure imgb0009
     un atome de phosphore ou d'azote substitué ou un atome de soufre,
    Ra est un radical alkyle à longue chaîne ayant de 7 à 21 atomes de C,
    X est un radical issu des groupes -O-C(O)-, -(O)C-O-, -NH-C(O)-, -(O)C-NH-, -(CH3)N-C(O)-, -(O)C-N(CH3)-, -S(O2)-O-, -0-S(02)-, -S(O2)-NH-, -NH-S(02)-, -S(02)-N(CH3)-, -N(CH3)-S(02)-,
    Rb, Rc sont des radicaux alkyle ayant 1 à 4 atomes de C, indépendants l'un de l'autre et le cas échéant ramifiés, ceux-ci pouvant contenir le cas échéant des substituants d'hétéroatome;
    les radicaux
    Rd Re sont choisis indépendamment l'un de l'autre parmi l'hydrogène (H), des radicaux alkyle ayant de 1 à 4 atomes de C, le cas échéant ramifiés, des radicaux aryle ou benzyle, le cas échéant substitués, ainsi que du CH2COOH, CH2COOR, CH2CH2COOH, CH2CH2COOR,
    Rf est un radical hydrocarbure ramifié et/ou substitué et/ou cyclique ayant de 1 à 10, de manière préférée 2 ou 3 atomes de carbon, et contenant le cas échéant des liaisons multiples, ou un radical styrène ou est constitué exclusivement de radicaux éthylène, propylène, butylène ou styrène ou est un polymère statistique ou un copolymère en bloc contenant les radicaux cités,
    Rg est un radical hydrocarbure ayant de 1 à 30 atomes de C, le cas échant ramifié, contenant le cas échéant des liaisons doubles, le cas échant cyclique,
    Z est un radical issu des groupes atome d'azote, atome d'oxygène, -0-C(0)-, -NH-C(0)-, - (CH3)N-C (0) -,
    n = 1, quand Z n'est pas un atome d'azote et o = 1;
    n = 2, quand Z est un atome d'azote et o = 1;
    n = 1, quand Z n'est pas un atome d'azote et o = 2,
    k et l valent de 1 à 4 indépendamment l'un de l'autre,
    k valant de manière préférée 2 ou 3, et
    l valant de manière préférée 1,
    m possède une valeur de 0 à 30, de manière préférée de 1 à 10, en particulier de 3 à 7 et
    A- est un anion et
    un assouplissant d'esterquat liquide du commerce.
  2. Formulations assouplissantes pour le linge selon la revendication 1, caractérisées en ce que le radical Ra des dérivés d'ester de bétaïne comporte un radical alkyle à longue chaîne ayant de 9 à 17 atomes de C.
  3. Formulations assouplissantes pour le linge selon la revendication 1 ou 2, caractérisées en ce que Y selon la formule (II) est un atome de phosphore ou un atome d'azote substitué et les radicaux Rb et Rc sont simultanément du -CH3.
  4. Formulations assouplissantes pour le linge selon l'une quelconque des revendications 1 à 3, caractérisées en ce que les radicaux Rd et Re sont simultanément de l'hydrogène.
  5. Formulations assouplissantes pour le linge selon l'une quelconque des revendications 1 à 4, caractérisées en ce que X = -C(O)-NH- ou C(O)-N(CH3)-.
  6. Formulations assouplissantes pour le linge selon l'une quelconque des revendications 1 à 5, caractérisées en ce que n = 1 et o = 1, ainsi que Z est un atome d'oxygène.
  7. Formulations assouplissantes pour le linge selon l'une quelconque des revendications 1 à 6, caractérisées en ce que k = 2 ou 3 et 1 = 1.
  8. Formulations assouplissantes pour le linge selon l'une quelconque des revendications 1 à 7, caractérisées en ce que Rf est un radical éthylène ou un radical propylène.
  9. Formulations assouplissantes pour le linge selon l'une quelconque des revendications 1 à 8, caractérisées en ce que m = 1 à 10 et Rg est un radical alkyle ayant de 1 à 30 atomes de C.
  10. Formulations assouplissantes pour le linge selon l'une quelconque des revendications 3 à 9, caractérisées en ce que Y selon la formule (II) est un atome de phosphore ou d'azote substitué, Ra est un radical alkyle ayant de 7 à 21 atomes de C, de manière préférée un radical alkyle à longue chaîne ayant de 9 à 17 atomes de C, X = -C(O)-NH-, Rb et Rc = -CH3, Rd et Re sont simultanément de l'hydrogène, Rf est un radical éthylène ou un radical propylène, de manière préférée un radical éthylène, n = 1, o = 1 et Z est un atome d'oxygène, ainsi que k = 3, 1 = 1, m = 2 et Rg est un radical alkyle ayant de 6 à 22, en particulier de 8 à 18 atomes de C.
  11. Procédé d'amélioration de la performance de lavage de lessives, comprenant les étapes :
    (A)élimination de l'alcalinité résultante du programme de lavage;
    (B)traitement secondaire du linge propre à des valeurs pH inférieures à 3,5 avec une formulation assouplissante pour le linge selon l'une quelconque des revendications 1 à 11 et
    (C)lavage du linge sali par l'usage ou d'autre manière avec une lessive en milieu aqueux alcalin.
EP03718759A 2002-04-20 2003-04-15 Compositions d'adoucissant textile contenant des derives d'ester de betaine et procede d'amelioration du pouvoir lavant de lessives Expired - Lifetime EP1497402B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10217705 2002-04-20
DE10217705A DE10217705A1 (de) 2002-04-20 2002-04-20 Wäscheweichspülformulierungen enthaltend Betainesterderivate sowie Verfahren zur Verbesserung der Waschleistung von Waschmitteln
PCT/EP2003/003912 WO2003089558A1 (fr) 2002-04-20 2003-04-15 Compositions d'adoucissant textile contenant des derives d'ester de betaine et procede d'amelioration du pouvoir lavant de lessives

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EP1497402A1 EP1497402A1 (fr) 2005-01-19
EP1497402B1 true EP1497402B1 (fr) 2007-02-28

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US (1) US7056878B2 (fr)
EP (1) EP1497402B1 (fr)
AT (1) ATE355353T1 (fr)
AU (1) AU2003222815A1 (fr)
CA (1) CA2482998A1 (fr)
DE (2) DE10217705A1 (fr)
WO (1) WO2003089558A1 (fr)

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Publication number Priority date Publication date Assignee Title
DE10217705A1 (de) * 2002-04-20 2003-11-06 Goldschmidt Ag Th Wäscheweichspülformulierungen enthaltend Betainesterderivate sowie Verfahren zur Verbesserung der Waschleistung von Waschmitteln
US8791045B2 (en) 2011-11-09 2014-07-29 Kimberly-Clark Worldwide, Inc. Non-tacky wetness indicator composition for application on a polymeric substrate
US9889222B2 (en) 2011-11-09 2018-02-13 Kimberly-Clark Worldwide, Inc. Aqueous medium-sensitive coating compositions for triggered release of active ingredients and visual indication for wetness
US20130338227A1 (en) 2012-06-13 2013-12-19 Marie-Esther Saint Victor Green Glycine Betaine Derivative Compounds And Compositions Containing Same
US9585826B2 (en) 2012-11-07 2017-03-07 Kimberly-Clark Worldwide, Inc. Triggerable compositions for two-stage, controlled release of active chemistry
US9119780B2 (en) 2013-10-30 2015-09-01 Kimberly-Clark Worldwide, Inc. Triggerable compositions for two-stage, controlled release of proactive chemistry
US9890350B2 (en) 2015-10-28 2018-02-13 Ecolab Usa Inc. Methods of using a soil release polymer in a neutral or low alkaline prewash

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US2742434A (en) 1952-01-19 1956-04-17 Gen Aniline & Film Corp Cleaner-sanitizer
US3539520A (en) 1967-07-12 1970-11-10 West Laboratories Inc Compositions comprising quaternary ammonium germicides and nonionic surfactants
AU5697073A (en) 1972-07-10 1974-12-19 Colgate Palmolive Co Liquid cleaner liquid cleaner
US3959157A (en) 1973-06-04 1976-05-25 Colgate-Palmolive Company Non-phosphate detergent-softening compositions
US3951879A (en) 1973-12-14 1976-04-20 Colgate-Palmolive Company Detergent that reduces electrostatic cling of synthetic fabrics
US4260529A (en) 1978-06-26 1981-04-07 The Procter & Gamble Company Detergent composition consisting essentially of biodegradable nonionic surfactant and cationic surfactant containing ester or amide
US4239660A (en) 1978-12-13 1980-12-16 The Procter & Gamble Company Detergent composition comprising a hydrolyzable cationic surfactant and specific alkalinity source
US4370272A (en) 1980-01-14 1983-01-25 Stepan Chemical Company Alkoxylated quaternary ammonium surfactants
DE3505269A1 (de) 1985-02-15 1986-08-21 Hoechst Ag, 6230 Frankfurt Quarternaere alkylamidobetainester, ein verfahren zu ihrer herstellung und ihre verwendung in waescheweichspuelmitteln
DE19520884A1 (de) * 1995-06-08 1996-12-12 Wella Ag Wasserhaltiges Weichspülmittel fürdie Behandlung von Textilien
EP0799885A1 (fr) * 1996-04-01 1997-10-08 The Procter & Gamble Company Composés bétaine ester des aclcools actifs
DE10153183A1 (de) * 2001-10-27 2003-05-15 Henkel Kgaa Betainesterhaltige Mittel
DE10217705A1 (de) * 2002-04-20 2003-11-06 Goldschmidt Ag Th Wäscheweichspülformulierungen enthaltend Betainesterderivate sowie Verfahren zur Verbesserung der Waschleistung von Waschmitteln

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CA2482998A1 (fr) 2003-10-30
DE50306660D1 (de) 2007-04-12
WO2003089558A1 (fr) 2003-10-30
AU2003222815A1 (en) 2003-11-03
DE10217705A1 (de) 2003-11-06
ATE355353T1 (de) 2006-03-15
US7056878B2 (en) 2006-06-06
EP1497402A1 (fr) 2005-01-19
US20050227904A1 (en) 2005-10-13

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