EP1007614A1 - Melanges detergents a fort pouvoir moussant contenant des sulfates d'ester de polyglycol d'acide gras - Google Patents

Melanges detergents a fort pouvoir moussant contenant des sulfates d'ester de polyglycol d'acide gras

Info

Publication number
EP1007614A1
EP1007614A1 EP98945253A EP98945253A EP1007614A1 EP 1007614 A1 EP1007614 A1 EP 1007614A1 EP 98945253 A EP98945253 A EP 98945253A EP 98945253 A EP98945253 A EP 98945253A EP 1007614 A1 EP1007614 A1 EP 1007614A1
Authority
EP
European Patent Office
Prior art keywords
fatty acid
sulfates
ether
detergent mixtures
alkyl
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.)
Withdrawn
Application number
EP98945253A
Other languages
German (de)
English (en)
Inventor
Hermann Hensen
Ullrich Bernecker
Jörg KAHRE
Werner Seipel
Holger Tesmann
Thomas Engels
Hans-Christian Raths
Bernd Fabry
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Personal Care and Nutrition GmbH
Original Assignee
Cognis Deutschland GmbH and Co KG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from DE19736906A external-priority patent/DE19736906A1/de
Priority claimed from DE19741911A external-priority patent/DE19741911C1/de
Application filed by Cognis Deutschland GmbH and Co KG filed Critical Cognis Deutschland GmbH and Co KG
Publication of EP1007614A1 publication Critical patent/EP1007614A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005Other compounding ingredients characterised by their effect
    • C11D3/0094High foaming compositions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86Polyethers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/02Preparations for cleaning the hair
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/24Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
    • C07C67/26Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran with an oxirane ring
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2603Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
    • C08G65/2615Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen the other compounds containing carboxylic acid, ester or anhydride groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2642Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
    • C08G65/2669Non-metals or compounds thereof
    • C08G65/2672Nitrogen or compounds thereof
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    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/28Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
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    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/37Mixtures of compounds all of which are anionic
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    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/65Mixtures of anionic with cationic compounds
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    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/83Mixtures of non-ionic with anionic compounds
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    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/86Mixtures of anionic, cationic, and non-ionic compounds
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    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88Ampholytes; Electroneutral compounds
    • C11D1/94Mixtures with anionic, cationic or non-ionic compounds
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    • C11D10/00Compositions of detergents, not provided for by one single preceding group
    • C11D10/04Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
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    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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    • C11D10/00Compositions of detergents, not provided for by one single preceding group
    • C11D10/04Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
    • C11D10/042Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap based on anionic surface-active compounds and soap
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    • C11D17/00Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0008Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
    • C11D17/003Colloidal solutions, e.g. gels; Thixotropic solutions or pastes
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    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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    • C11D17/00Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0047Detergents in the form of bars or tablets
    • C11D17/006Detergents in the form of bars or tablets containing mainly surfactants, but no builders, e.g. syndet bar
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    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/06Powder; Flakes; Free-flowing mixtures; Sheets
    • C11D17/065High-density particulate detergent compositions
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    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/02Inorganic compounds ; Elemental compounds
    • C11D3/12Water-insoluble compounds
    • C11D3/124Silicon containing, e.g. silica, silex, quartz or glass beads
    • C11D3/1246Silicates, e.g. diatomaceous earth
    • C11D3/128Aluminium silicates, e.g. zeolites
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    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/2075Carboxylic acids-salts thereof
    • C11D3/2082Polycarboxylic acids-salts thereof
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    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
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    • C11D3/2086Hydroxy carboxylic acids-salts thereof
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    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/22Carbohydrates or derivatives thereof
    • C11D3/222Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
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    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
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    • C11D1/04Carboxylic acids or salts thereof
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    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
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    • C11D1/06Ether- or thioether carboxylic acids
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    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/146Sulfuric acid esters
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    • C11D1/02Anionic compounds
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    • C11D1/29Sulfates of polyoxyalkylene ethers
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    • C11D1/38Cationic compounds
    • C11D1/52Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/523Carboxylic alkylolamides, or dialkylolamides, or hydroxycarboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain one hydroxy group per alkyl group
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    • C11D1/38Cationic compounds
    • C11D1/52Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/525Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain two or more hydroxy groups per alkyl group, e.g. R3 being a reducing sugar rest
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Definitions

  • the invention relates to strongly foaming detergent mixtures containing low alkoxylated fatty acid polyglycol ester sulfates and to the use of these substances as foam boosters for surfactant mixtures.
  • the base foam is high, but disintegrates quickly, in the other case it is exactly the opposite, ie the foaming behavior is rather average, but the foam remains stable for a long time. If these properties can be combined with one another in an advantageous manner, it is found that the mixtures either do not tolerate water hardness or oil pollution. As a result, the number of surfactant combinations that meet this complex requirement profile is rather small, which is why the same formulations are always found on the market.
  • One way to avoid this problem is to add surfactant formulations, so-called foam boosters, which have a favorable effect on the foam properties of the mixtures.
  • a typical group of compounds that can be used for this purpose are the fatty acid alkanolamides, which, however, have the disadvantage that they themselves have no surfactant properties have, so for example make no contribution to cleansing ability, and are also still suspected of being able to contain traces of nitrosamines, which is absolutely undesirable for applications in which the preparations come into contact with human skin.
  • the complex object of the invention was therefore to provide surface-active preparations which are free from the disadvantages described above.
  • the invention relates to strongly foaming detergent mixtures containing
  • R 1 CO is a linear or branched, saturated or unsaturated acyl radical having 6 to 22 carbon atoms
  • x is an average of 1 to 3
  • AO is a CH2CH2O-, CH 2 CH (CH 3 ) 0- and / or CH ( CH 3 ) CH 2 0 radical
  • X represents an alkali and / or alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucammonium, and
  • low alkoxylated fatty acid polyglycol ester sulfates which themselves have no pronounced foam properties, are foam boosters, that is to say they improve both the base foam and the foam stability of other surfactants in a synergistic manner.
  • the invention includes the knowledge that these synergistic effects are also obtained in hard water and in the presence of oil (sebum) and apply to a wide range of surfactants.
  • Another advantage of the invention is that the fatty acid polyglycol esters have solubilizing properties and thus improve the formulation of surfactants which are otherwise poorly soluble in cold water.
  • the foam boosters have sufficient detergent properties so that, in contrast to, for example, alkanolamides, they contribute to the cleaning ability. After all, the substances are harmless from a skin cosmetic point of view, easily biodegradable and of course free of nitrosamines.
  • Fatty acid polyglycol ester sulfates are produced by sulfating the corresponding fatty acid polyglycol esters. These in turn can be obtained by the relevant preparative methods of organic chemistry. For this purpose, ethylene oxide, propylene oxide or a mixture thereof - in random or block distribution - is added to the corresponding fatty acids, this reaction catalyzing acid, but preferably in the presence of bases, such as, for example, sodium methylate or calcined hydrotalcite. If a degree of alkoxylation of 1 is desired, the intermediates can also be prepared by esterifying the fatty acids with an appropriate alkylene glycol.
  • the sulfation of the fatty acid polyglycol esters can be carried out in a manner known per se with chlorosulfonic acid or preferably gaseous sulfur trioxide are carried out, the molar ratio between fatty acid polyglycol ester and sulfating agent in the range from 1 0.95 to 1 1, 2, preferably 1 1 to 1 1, 1 and the Re action temperature can be 30 to 80 and preferably 50 to 60 ° C. It is also possible to undersulfate the fatty acid polyglycol esters, ie to use significantly less sulfating agents than would be required for complete stoichiometric conversion.
  • fatty acid polyglycol ester to sulfating agent for example, if molar amounts of fatty acid polyglycol ester to sulfating agent are selected from 1 0 , 5 to 1 0.95 mixtures of fatty acid polyglycol ester sulfates and fatty acid polyglycol esters are obtained, which are also advantageous for a whole range of applications.
  • Typical examples of suitable starting materials are the addition products of 1 to 3 moles of ethylene oxide and / or propylene oxide, but preferably the adducts with 1 mole of ethylene oxide or 1 mole of propylene oxide with caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid , Lau ⁇ nsaure, Is ot ⁇ decansaure, My ⁇ stmsaure, Palmitinsaure, Palmoleinsaure, Stearinsaure, Isosteannsaure, Olsaure, Elaidinsaure, Petroselinsaure, Linolklare, Linolenenklare, Elaeaussteins ⁇ nsaure, Arachinsaure, Gadolseinsaure, asensate acid as well assulfate and technical grade desulphates as described and desulfates as described above and are described as technical neutralizers and desulfates, as well as mixtures
  • Nonionic, anionic, cationic and / or amphoteric or amphoteric surfactants can be included as surface-active substances.
  • anionic surfactants are soaps, alkylbenzenes. sulfonates, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether, ⁇ -methyl ester sulfonates, sulfofatty acids mischethersulfate, alkyl sulfates, fatty alcohol ether sulfates, Glycerol ether, hydroxy, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates, mono- and Dialkylsulfo- succinate, mono- and Dialkylsulfosuccinamates, sulfotriglycerides, amide soaps, ether carboxylic acids and their salts, amidether carboxylic
  • anionic surfactants contain polyglycol ether chains, these can have a conventional, but preferably a narrow, homolog distribution.
  • Typical examples of nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers or mixed formals, optionally partially oxidized alk (en) yl oligoglycosides, or glucoramic acid derivatives, in particular, glucoronic acid derivatives (FGU) -glucoronic acid derivatives (GLC) -sulfuric acid derivatives (GLCUs), and glucoronic acid derivatives (GLCUs), in particular glucoronic acid derivatives (GLCUs) Wheat base), polyol fatty acid esters, sugar esters, sorbitan esters, polysorbates and amine oxide
  • nonionic surfactants contain polyether glycol ether chains, these can have a conventional, but preferably a narrow, homolog distribution.
  • Typical examples of cationic surfactants are quaternary tetraalkylammonium compounds and ester quats, in particular quaternized difatty acid trialkanolamine or difatty acid methyldiethanolamine ester salts.
  • Typical examples of amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amidobetaines, aminopropionates, aminoglycinates, imidazolinium betaines and sulfobetaines. The surfactants mentioned are exclusively known compounds. With regard to the structure and manufacture of these substances, relevant review articles include, for example, J.
  • the detergent mixtures can contain the components (a) and (b) in a weight ratio of 90 AO to 10:90, preferably 75:25 to 25:75 and in particular in a ratio of 60:40 to 40:60.
  • Preferred binary or ternary combinations are those of lauric acid or coconut fatty acid + 1 EO sulfate sodium or ammonium salt with alkyl ether sulfates, fatty acid monoglyceride sulfates, alkyl oligoglucosides and / or betaines.
  • the fatty acid polyglycol ester sulfates of the formula (I) also improve the foaming behavior and the foam resistance of a large number of surfactants in a synergistic manner even when water hardness and oil pollution are present.
  • Another object of the invention therefore relates to their use as foam boosters to improve the foam properties of anionic, nonionic, cationic and / or amphoteric or zwitterionic surfactants. Examples
  • aqueous surfactant solutions 21 ° dH, + 1% by weight sebum
  • the foam volume was determined in accordance with DIN standard 53 902, part 1.
  • the foam is created by beating the liquid sample in a standing cylinder with a horizontally aligned perforated plate attached to a stem for 30 seconds.
  • the resulting foam volume is measured immediately after completion of the shaving, as well as after 1, 5 and 20 minutes.
  • the results are summarized in Tables 1 to 3.
  • the following surfactants were used (quantitative data as% by weight).

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Abstract

L'invention concerne des mélanges détergents à fort pouvoir moussant contenant (a) des sulfates d'ester de polyglycol d'acide gras de la formule (I), R1COO(AO)¿x?SO3X dans laquelle R?1¿CO désigne un reste acyle linéaire ou ramifié, saturé ou non saturé ayant entre 6 et 22 atomes de carbone, x désigne des nombres compris entre 1 et 3 et AO désigne un reste CH¿2?CH2O-, CH2CH(CH3)O- et/ou CH(CH3)CH2O- et X désigne un métal alcalin et/ou alcalino-terreux, ammonium, alkylammonium, alcanolammonium ou glucammonium, et (b) d'autres tensioactifs anioniques, non ioniques, cationiques, amphotères et/ou zwitterioniques. Ces mélanges se caractérisent en ce qu'ils présentent, même en cas de dureté de l'eau et de sollicitation par des graisses, un comportement avantageux en termes de moussage et une stabilité de mousse élevée.
EP98945253A 1997-08-25 1998-08-17 Melanges detergents a fort pouvoir moussant contenant des sulfates d'ester de polyglycol d'acide gras Withdrawn EP1007614A1 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE19736906A DE19736906A1 (de) 1997-08-25 1997-08-25 Verfahren zur Herstellung von sulfatierten Fettsäurealkylenglykolestern
DE19736906 1997-08-25
DE19741911A DE19741911C1 (de) 1997-09-25 1997-09-25 Stark schäumende Detergensgemische
DE19741911 1997-09-25
PCT/EP1998/005210 WO1999010461A1 (fr) 1997-08-25 1998-08-17 Melanges detergents a fort pouvoir moussant contenant des sulfates d'ester de polyglycol d'acide gras

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EP1007614A1 true EP1007614A1 (fr) 2000-06-14

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EP98945253A Withdrawn EP1007614A1 (fr) 1997-08-25 1998-08-17 Melanges detergents a fort pouvoir moussant contenant des sulfates d'ester de polyglycol d'acide gras

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US (1) US6235696B1 (fr)
EP (1) EP1007614A1 (fr)
JP (1) JP2001514302A (fr)
AU (1) AU9263198A (fr)
WO (1) WO1999010461A1 (fr)

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Publication number Priority date Publication date Assignee Title
WO1999049007A1 (fr) * 1998-03-25 1999-09-30 Henkel Kommanditgesellschaft Auf Aktien Produit vaisselle comprenant des sulfates d'ester d'oligoalkylenglycol d'acide gras
DE19904847A1 (de) 1999-02-08 2000-08-10 Rwe Dea Ag Öl-in-Wasser-Mikroemulsion enthaltend Alkanolammonium-Salze der Alkylsulfate und/oder Alkylpolyalkylenglykolethersulfate
DE19937293A1 (de) * 1999-08-06 2001-02-15 Cognis Deutschland Gmbh Verwendung von alkoxylierten Carbonsäureestern als Schaumboostern
DE10045289A1 (de) * 2000-09-13 2002-03-28 Henkel Kgaa Schnell trocknendes Wasch- und Reinigungsmittel, insbesondere Handgeschirrspülmittel
DE10233330B4 (de) * 2002-07-22 2007-04-26 Sasol Germany Gmbh Mikroemulsion enthaltend UV-Lichtschutzfilter und/oder Antischuppenmittel
ATE463283T1 (de) * 2004-02-27 2010-04-15 Henkel Ag & Co Kgaa Verwendung kationischer stärkederivate zum farberhalt
DE102006051729A1 (de) * 2006-10-30 2008-05-08 Henkel Kgaa Kosmetisches Mittel
ES2813748T3 (es) 2014-12-19 2021-03-24 Oreal Composición cosmética anhidra sólida, procedimiento de preparación, procedimientos de tratamiento cosmético, y kit asociado

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Publication number Priority date Publication date Assignee Title
GB1498692A (en) 1975-01-29 1978-01-25 Ciba Geigy Ag Detergent composition
US4412944A (en) 1980-02-12 1983-11-01 Alcolac, Inc. High foaming, low eye irritation cleaning compositions containing ethoxylated anionic (C13-C30) sulphates
JPH06293620A (ja) * 1993-04-02 1994-10-21 Miyoshi Oil & Fat Co Ltd シャンプー組成物
EP0748368A1 (fr) * 1994-02-28 1996-12-18 Colgate-Palmolive Company Detergent liquide

Non-Patent Citations (1)

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Title
See references of WO9910461A1 *

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AU9263198A (en) 1999-03-16
WO1999010461A1 (fr) 1999-03-04
US6235696B1 (en) 2001-05-22
JP2001514302A (ja) 2001-09-11

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