WO1996041858A1 - Solution tensioactive diluee a forte viscosite - Google Patents

Solution tensioactive diluee a forte viscosite Download PDF

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Publication number
WO1996041858A1
WO1996041858A1 PCT/EP1996/002387 EP9602387W WO9641858A1 WO 1996041858 A1 WO1996041858 A1 WO 1996041858A1 EP 9602387 W EP9602387 W EP 9602387W WO 9641858 A1 WO9641858 A1 WO 9641858A1
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Prior art keywords
carbon atoms
alkyl
surfactant mixtures
mixtures according
contain
Prior art date
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PCT/EP1996/002387
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German (de)
English (en)
Inventor
Thomas Förster
Jörg KAHRE
Markus Sumser
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Henkel Kommanditgesellschaft Auf Aktien
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Publication of WO1996041858A1 publication Critical patent/WO1996041858A1/fr

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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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
    • C11D17/003—Colloidal solutions, e.g. gels; Thixotropic solutions or pastes
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/04—Carboxylic acids or salts thereof
    • C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/146—Sulfuric acid esters
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene ethers
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/32—Protein hydrolysates; Fatty acid condensates thereof
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives
    • 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 dilute aqueous surfactant solutions with increased viscosity, containing selected ternary surfactant mixtures based on alkyl and / or alkenyl ligoglycosides, betaines and selected other surfactants.
  • the complex object of the invention was therefore to provide aqueous surfactant mixtures based on alkyl and / or alkenyl oligoglucosides which, despite their high dilution, have a sufficiently high viscosity without the necessity of using organic thickeners.
  • the invention relates to dilute surfactant mixtures with increased viscosity, containing 30 to 70% by weight of alkyl and / or alkenyl oligoglycosides, based on the surfactant content a),
  • co-surfactants selected from the group consisting of fatty alcohol ether sulfates, monoglyceride (ether) sulfates, acylglutamates and protein hydrolyzates, with the proviso that the amounts add up to 100% by weight of active substance.
  • ternary mixtures of the type mentioned show viscoelastic behavior and a viscosity (shear rate 1 / s) in the range from 1,000 to 50,000 mPas even in dilute aqueous solution.
  • Alkyl and alkenyl oligoglycosides are known nonionic surfactants which follow the formula (I) R 1 O- [G] p (I) in which R 1 is an alkyl and / or alkenyl radical having 4 to 22 carbon atoms, G is a sugar radical having 5 or 6 carbon atoms and p is a number from 1 to 10. They can be obtained according to the relevant procedures in preparative organic chemistry. As representative of the extensive literature, reference is made here to the documents EP-A1-0 301 298 and WO 90/03977.
  • the alkyl and / or alkenyl oligoglycosides can be derived from aldoses or ketoses with 5 or 6 carbon atoms, preferably glucose. The preferred alkyl and / or alkenyl oligoglycosides are thus alkyl and / or alkenyl oligoglucosides.
  • the alkyl or alkenyl radical R 1 can be derived from primary alcohols having 4 to 11, preferably 8 to 10, carbon atoms. Typical examples are butanol, capron alcohol, caprylic alcohol, capric alcohol and undecyl alcohol and their technical mixtures, such as are obtained, for example, in the hydrogenation of technical fatty acid methyl esters or in the course of the hydrogenation of aldehydes from Roelen's oxosynthesis.
  • the alkyl or alkenyl radical R 1 can also be derived from primary alcohols having 12 to 22, preferably 12 to 14, carbon atoms. Typical examples are lauryl alcohol, Myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol and their technical mixtures, which can be obtained as described above. Alkyl oligoglucosides based on hardened C 12/14 coconut alcohol with a DP of 1 to 3 are preferred.
  • Betaines are known surfactants which are predominantly produced by carboxyalkylation, preferably carboxymethylation, of aminic compounds.
  • the starting materials are preferably condensed with halocarboxylic acids or their salts, in particular with sodium chloroacetate, one mol of salt being formed per mole of betaine.
  • unsaturated carboxylic acids such as acrylic acid is also possible.
  • betaines and "real" amphoteric surfactants reference is made to the contribution by U.Ploog in Seifen- ⁇ le-Fette-Wwachs, 198, 373 (1982). Further overviews on this topic can be found for example by A. O'Lennick et al.
  • betaines are the carboxyalkylation products of secondary and in particular tertiary amines which follow the formula (I)
  • R 2 for alkyl and / or alkenyl radicals with 6 to 22 carbon atoms
  • R 3 for hydrogen or alkyl radicals with 1 to 4 carbon atoms
  • R 4 for alkyl radicals with 1 to 4 carbon atoms
  • n for numbers from 1 to 6
  • X for is an alkali and / or alkaline earth metal or ammonium.
  • Typical examples are are the carboxymethylation products of Hexylmethyl-amine, hexyldimethylamine, octyldimethylamine, decyldimethylamine, dodecylmethylamine, Do- decyldimethylamine, Dodecylethylmethylamin, C dimethylamine 12/14 -Kokosalkyldimethylamin, myristyl, cetyldimethylamine, stearyldimethylamine methylamine, stearyl, Oleyldi-, C 16/18 -Talgalkyldimethylamin and their technical mixtures.
  • R 5 CO represents an aliphatic acyl radical having 6 to 22 carbon atoms and 0 or 1 to 3 double bonds
  • m represents numbers from 1 to 3 and R 3 , R 4 , n and X have the meanings given above.
  • Typical examples are reaction products of fatty acids with 6 to 22 carbon atoms, namely caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, elaeostearic acid, gadoleic acid and arachic acid, arachic acid and their technical mixtures, with N, N-dimethylaminoethylamine, N, N-dimethylaminopropylamine, N, N-diethylaminoethylamine and N, N-diethylaminopropylamine, which are condensed with sodium chloroacetate.
  • R 6 is an alkyl radical having 5 to 21 carbon atoms
  • R 7 is a hydroxyl group
  • an OCOR 6 or NHCOR 6 radical and m is 2 or 3.
  • These substances are also known substances which can be obtained, for example, by cyclizing condensation of 1 or 2 moles of fatty acid with polyhydric amines such as, for example, aminoethylethanolamine (AEEA) or diethylene triamine.
  • AEEA aminoethylethanolamine
  • the corresponding carboxyalkylation products are mixtures of different open-chain betaines.
  • Typical examples are condensation products of the above-mentioned fatty acids with AEEA, preferably imidazolines based on lauric acid or again C 12/14 coconut fatty acid, which are subsequently betainized with sodium chloroacetate.
  • ether sulfates Fatty alcohol ether sulfates
  • CSA chlorosulfonic acid
  • ether sulfates which follow the formula (IV) are suitable
  • R 8 O- (CH 2 CH 2 O) m SO 3 Z (IV) in R 8 for a linear or branched alkyl and / or alkenyl radical with 6 to 22 carbon atoms, n for numbers from 1 to 10 and Z for a Alkali and / or alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucammonium.
  • Typical examples are the sulfates of addition products with an average of 1 to 10 and in particular 2 to 5 moles of ethylene oxide with caprone alcohol, caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostyl alcohol, ela-alcohol alcohol, ela-alcohol alcohol, ela-alcohol alcohol, Petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol and brassidyl alcohol and their technical mixtures, in the form of their sodium and / or magnesium salts.
  • the ether sulfates can have both a conventional and a narrow homolog distribution.
  • ether sulfates based on adducts of an average of 2 to 3 mol ethylene oxide with technical C 12/14 or C 12/18 coconut fatty alcohol fractions in the form of their sodium and / or magnesium salts.
  • Monoglyceride sulfates and monoglyceride ether sulfates are known anionic surfactants which can be obtained by the relevant methods of preparative organic chemistry.
  • the usual starting point for their preparation is triglycerides, which, if appropriate, are transesterified to the monoglycerides after ethoxylation and subsequently sulfated and neutralized.
  • suitable sulfating agents preferably gaseous sulfur trioxide or chlorosulfonic acid [cf. WO 92/09 569, WO 92/09 570 (Henkel)].
  • the neutralized substances can be subjected to ultrafiltration in order to reduce the electrolyte content to a desired level [DE-A1 42 04 700 (Henkel)].
  • R 9 CO stands for a linear or branched acyl radical with 6 to 22 carbon atoms, x, y and z in total for 0 or for numbers from 1 to 30, preferably 2 to 10, and Z stands for an alkali or alkaline earth metal.
  • Typical examples of monoglyceride (ether) sulfates suitable for the purposes of the invention are the reaction products of lauric acid monoglyceride, coconut fatty acid monoglyceride, palmitic acid monoglyceride, stearic acid monoglyceride, oleic acid monoglyceride and tallow fatty acid monoglyceride as well as their ethylene oxide adducts or their formulated with sulfuric acid trioxide.
  • Monoglyceride sulfates of the formula (V) are preferably used in which R 9 CO represents a linear acyl radical having 8 to 18 carbon atoms.
  • R 10 CO represents a linear or branched acyl radical having 6 to 22 carbon atoms and 0 and / or 1, 2 or 3 double bonds and Z represents hydrogen, an alkali metal and / or alkaline earth metal, ammonium, alkylammomum, alkanolammonium or glucammonium.
  • They are produced, for example, by Schotten-Baumann acylation of glutamic acid with fatty acids, fatty acid esters or chlorides. Sales products are available, for example, from Hoechst AG, Frankfurt / DE or Ajinomoto Co. Inc., Tokyo / JP.
  • An overview of the production and properties of the acylglutamates can be found by M.Takehara et al. in J. Am. Oil. Chem. Soc, 49, 143 (1972). Mixtures of alkyl glucosides and acyl glutamates are described in Japanese patent application JP-A Hl / 178 597 (Shiseido).
  • glutamic acid is one of the products that would be obtained by total hydrolysis of proteins.
  • the hydrolysis of proteins leads to mixtures of oligopeptides which still have an average of 5 to 20 amino acid units.
  • conventional protein fatty acid condensates represent acylation products of oligopeptides.
  • Acylglutamates differ from these substances in that they represent "monomers" to a certain extent.
  • acylglutamates which are suitable for the purposes of the invention are anionic surfactants which are derived from fatty acids having 6 to 22, preferably 12 to 18 carbon atoms, such as C 12/14 - or C 12/18 - Coconut fatty acid, lauric acid, myristic acid, palmitic acid and / or stearic acid.
  • anionic surfactants which are derived from fatty acids having 6 to 22, preferably 12 to 18 carbon atoms, such as C 12/14 - or C 12/18 - Coconut fatty acid, lauric acid, myristic acid, palmitic acid and / or stearic acid.
  • Sodium N-cocoyl and sodium N-stearoyl-L-glutamate are particularly preferred.
  • Protein hydrolysates are degradation products of animal or vegetable proteins, for example collagen, elastin or keratin and preferably almond and potato protein and in particular wheat and soy protein, which are cleaved by acidic, alkaline and / or enzymatic hydrolysis and then have an average molecular weight in the range of 600 have up to 4000, preferably 2000 to 3500.
  • protein hydrolyzates do not represent a surfactant in the classic sense due to the lack of a hydrophobic residue, they are widely used for the formulation of surface-active agents because of their dispersing properties. Overviews of the manufacture and use of Protein hydrolyzates are, for example, from G. Schuster and A. Domsch in Seifen ⁇ le Fette Wachsen, 108, 177 (1982) and Cosm.Toil, respectively. 99, 63 (1984), by HW Steisslinger in Parf.
  • liquid personal cleansing agents are also known which, in addition to alkyl glucosides and protein hydrolyzates, can also contain betaines in minor amounts.
  • the mixtures according to the invention are prepared, for example, by mixing the individual surfactants with heating.
  • low-viscosity binary premixes are produced, for example from 25 to 75% by weight of the amount of component a) to be used and 100% of the amount of component c) on the one hand and on the other hand from the remaining amount of component a) and 100% by weight of component b);
  • Components a) and b) are interchangeable in this example.
  • the surfactant mixtures according to the invention preferably contain components a), b) and c) in the weight ratios (30 to 50): (15 to 35): (15 to 35).
  • Diluted agents are to be understood as meaning those which have an active substance content (non-aqueous content) in the range from 5 to 20 and in particular 10 to 15% by weight.
  • the surfactant mixtures according to the invention are distinguished by a sufficiently high viscosity in the range from 1,000 to 50,000 mPas (shear rate 1 / s) and advantageous oscillating properties. They are suitable, for example, for cleaning hard surfaces and in particular as body and hair cleaning and care products, such as, for example, hair shampoos, hair lotions or bubble baths, and can be used in this connection as typical ingredients, emulsifiers, and over contain greasing agents, thickening agents, cation polymers, silicone compounds, biogenic agents, film formers, preservatives, colorants and fragrances.
  • Suitable emulsifiers are both known W / O and O / W emulsifiers such as, for example, hardened and ethoxylated castor oil, polyglycerol fatty acid esters or polyglycerol polyricinoleates or polyglycerol poly-12-hydroxystearates.
  • Substances such as, for example, polyethoxylated lanolin derivatives, lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers.
  • Suitable thickeners are, for example, polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, and also higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, polyvinyl alcohol and polyvinylpyrrolidone, surfactants such as, for example, fatty alcohol distribution with fatty alcohols such as fatty alcohol or alkyl oligoglucosides and electrolytes such as table salt and ammonium chloride.
  • polysaccharides in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, and also higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, polyvinyl alcohol and polyvinylpyrrolidone, surfactants such
  • Suitable cationic polymers are, for example, cationic cellulose derivatives, cationic starch, copolymers of diallylammonium salts and acrylamides, quaternized Vmylpyrrolidon / vinylimidazole polymers such as, for example, Luviquat® (BASF AG, Ludwigshafen / FRG), condensation products of polyglycols and amines, such as, for example, collagen hydrolyzylated collagen polypolyphenolated collagen polypropylene (Lamequat®L, Grünau GmbH), polyethyleneimine, cationic silicone polymers such as Amidomethicone or Dow Corning, Dow Corning Co./US, copolymers of adipic acid and dimethylaminohydroxypropyldiethylenetrimamine (Cartaretine®, Sandoz / CH), polyaminopolyamides as described, for example, in FR-A 22 52 840 and their crosslinked water-soluble polymers, cationic chitin derivatives such
  • Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, cyclic silicones and amino, fatty acid, alcohol, polyether, epoxy, fluorine and / or alkyl modified silicone compounds.
  • Biogenic active substances are understood to mean, for example, plant extracts and vitamin complexes.
  • Common film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpy ⁇ Olidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid or its salts and similar compounds.
  • Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid.
  • Suitable pearlizing agents are, for example, glycol distearic acid esters such as ethylene glycol distearate, but also fatty acid monoglycol esters.
  • the dyes which can be used are those substances which are suitable and approved for cosmetic purposes, as compiled, for example, in the publication "Cosmetic Dyes” by the Dye Commission of the German Research Foundation, Verlag Chemie, Weinheim, 1984, pp. 81-106. These dyes are usually used in concentrations of 0.001 to 0.1% by weight, based on the mixture as a whole.
  • the total proportion of auxiliaries and additives can be 1 to 50, preferably 5 to 40% by weight, based on the composition.
  • aqueous surfactant mixtures with an active substance content of 12% by weight, optionally with the addition of 1 to 3% by weight of sodium chloride, based on the solids content of the mixtures, were investigated at 20 ° C. in a Rheometrics RFSII rotary rheometer.
  • the viscosity was determined at a shear rate of 1 or 30 s / m and in oscillation experiments, the modulus of elasticity G 'and the viscosity modulus G ".
  • APG coconut alkyl oligoglucoside (Plantaren® APG 1200)
  • FAES fatty alcohol ether sulfate (Texapon® NSO)
  • ACG acylglutamate (Hostapon® KCG)
  • WPHY wheat protein hydrolyzate (Gluadin® WK)
  • CMGS coconut monoglyceride sulfate sodium salt

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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)
  • Dispersion Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne des mélanges tensioactifs dilués à forte viscosité, contenant comme constituants tensioactifs a) 30 à 70 % en poids d'alkyloligoglycosides et/ou d'alcényloligoglycosides, b) 15 à 50 % en poids de tensioactifs bétaïniques et c) 15 à 50 % en poids de co-tensioactifs choisis dans le groupe comprenant les sulfates d'éther d'alcools gras, les sulfates (éther)monoglycéridiques, les acylglutamates et les hydrolysats protéiques, à condition que les proportions donnent un total de 100 % en poids de substance active.
PCT/EP1996/002387 1995-06-12 1996-06-03 Solution tensioactive diluee a forte viscosite WO1996041858A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19521351.3 1995-06-12
DE1995121351 DE19521351A1 (de) 1995-06-12 1995-06-12 Verdünnte wäßrige Tensidlösungen mit erhöhter Viskosität

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Publication Number Publication Date
WO1996041858A1 true WO1996041858A1 (fr) 1996-12-27

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999027062A1 (fr) * 1997-11-26 1999-06-03 Henkel Kommanditgesellschaft Auf Aktien Detergent a vaisselle a profil de viscosite specifique
FR2826017A1 (fr) * 2001-06-15 2002-12-20 Cognis France Sa Melanges de tensioactifs
WO2011008281A1 (fr) 2009-07-14 2011-01-20 Rhodia Operations Compositions d'adjuvant agricole, compositions pesticides et procédés pour utiliser de telles compositions
WO2011034444A1 (fr) * 2009-09-17 2011-03-24 Polygon (Nz) Limited Formulations de tensioactifs herbicides

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998036041A1 (fr) * 1997-02-18 1998-08-20 Henkel Corporation Amelioration de l'activite de sulfate d'ether utilise dans des liquides de lavage delicat, au moyen d'alkylpolyglycoside
DE19805671C2 (de) * 1998-02-12 1999-12-16 Henkel Kgaa Verfahren zur Herstellung von trübungsfreien Detergensgemischen

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2398797A1 (fr) * 1977-07-26 1979-02-23 Albright & Wilson Compositions tensioactives aqueuses concentrees
WO1993016156A1 (fr) * 1992-02-07 1993-08-19 Henkel Kommanditgesellschaft Auf Aktien Melanges de detergents aqueux remarquablement bien toleres par la peau
WO1993025650A1 (fr) * 1992-06-16 1993-12-23 Henkel Corporation Compositions de concentres de tensioactifs a viscosite controlee
JPH06340891A (ja) * 1993-05-31 1994-12-13 Kao Corp 洗浄剤組成物
US5503779A (en) * 1995-03-20 1996-04-02 Colgate Palmolive Company High foaming light duty liquid detergent

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2398797A1 (fr) * 1977-07-26 1979-02-23 Albright & Wilson Compositions tensioactives aqueuses concentrees
WO1993016156A1 (fr) * 1992-02-07 1993-08-19 Henkel Kommanditgesellschaft Auf Aktien Melanges de detergents aqueux remarquablement bien toleres par la peau
WO1993025650A1 (fr) * 1992-06-16 1993-12-23 Henkel Corporation Compositions de concentres de tensioactifs a viscosite controlee
JPH06340891A (ja) * 1993-05-31 1994-12-13 Kao Corp 洗浄剤組成物
US5503779A (en) * 1995-03-20 1996-04-02 Colgate Palmolive Company High foaming light duty liquid detergent

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999027062A1 (fr) * 1997-11-26 1999-06-03 Henkel Kommanditgesellschaft Auf Aktien Detergent a vaisselle a profil de viscosite specifique
FR2826017A1 (fr) * 2001-06-15 2002-12-20 Cognis France Sa Melanges de tensioactifs
WO2002102949A1 (fr) * 2001-06-15 2002-12-27 Cognis France S.A. Melanges d'agents tensioactifs
US7279456B2 (en) 2001-06-15 2007-10-09 Gognis France S.A. Surfactant mixtures
WO2011008281A1 (fr) 2009-07-14 2011-01-20 Rhodia Operations Compositions d'adjuvant agricole, compositions pesticides et procédés pour utiliser de telles compositions
EP2453751A1 (fr) * 2009-07-14 2012-05-23 Rhodia Opérations Compositions d'adjuvant agricole, compositions pesticides et procédés pour utiliser de telles compositions
EP2453751A4 (fr) * 2009-07-14 2013-07-17 Rhodia Operations Compositions d'adjuvant agricole, compositions pesticides et procédés pour utiliser de telles compositions
WO2011034444A1 (fr) * 2009-09-17 2011-03-24 Polygon (Nz) Limited Formulations de tensioactifs herbicides
AU2010296099B2 (en) * 2009-09-17 2014-09-18 Kin-Wai Mok Herbicidal surfactant formulations

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