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WO1994027570A1 - Compositions tensioactives aqueuses - Google Patents

Compositions tensioactives aqueuses Download PDF

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Publication number
WO1994027570A1
WO1994027570A1 PCT/EP1994/001653 EP9401653W WO9427570A1 WO 1994027570 A1 WO1994027570 A1 WO 1994027570A1 EP 9401653 W EP9401653 W EP 9401653W WO 9427570 A1 WO9427570 A1 WO 9427570A1
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WO
WIPO (PCT)
Prior art keywords
weight
water
cationic
emulsion
preparation
Prior art date
Application number
PCT/EP1994/001653
Other languages
German (de)
English (en)
Inventor
Peter Busch
Gert-Lother Striepling
Klaus Thiele
Thomas Müller-Kirschbaum
Holger Tesmann
Armin Wadle
Jörg KAHRE
Werner Seipel
Hermann Hensen
Thomas Engels
Thomas Förster
Jürgen Stodt
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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
Application filed by Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to JP7500205A priority Critical patent/JPH08511292A/ja
Priority to EP94918356A priority patent/EP0701432A1/fr
Publication of WO1994027570A1 publication Critical patent/WO1994027570A1/fr

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/068—Microemulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/737—Galactomannans, e.g. guar; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/413—Nanosized, i.e. having sizes below 100 nm

Definitions

  • the invention relates to aqueous preparations with ionic surfactants which, through the addition of particularly finely divided emulsions of water-insoluble oil components, have an unusually high anti-aging effect for keratin surfaces and particularly desired effects on skin and hair.
  • Aqueous preparations of surface-active substances are used to clean and care for the body and hair. These often have the disadvantage that they swell the skin strongly, degrease the hair strongly and in this way contribute to a deterioration in the skin condition and the ability of the hair.
  • lipid-replenishing components usually in the form of water-solubilized fatty substances or oils which are clearly solubilized in the surfactant preparations.
  • lipid-replenishing components usually in the form of water-solubilized fatty substances or oils which are clearly solubilized in the surfactant preparations.
  • Such preparations are described, for example, in DE 3534 733.
  • emulsified oil or fat components has not proven itself, since such preparations are usually not sufficiently stable, but tend to inhomogeneity and oil separation when stored.
  • the foaming power is considerably impaired by the oil components which have a foam-suppressing action.
  • oil-in-water emulsions which were prepared with a combination of nonionic emulsifiers and co-emulsifiers and were heated to phase inversion temperature during or after their preparation.
  • Such emulsions are characterized by high stability, fine particle size and particularly low viscosity.
  • DE 38 19 193 discloses an emulsifier system which enables the production of such emulsions even with polar oils which contain little or no hydrocarbon content.
  • a further improved method is known from DE 41 40562.
  • PIT emulsions - The droplet diameter of such fine-particle emulsions - hereinafter referred to as PIT emulsions - is in the order of 100-300 nanometers (nm), i.e. they are not yet optically isotropic, single-phase systems such as are found in solubilizates and microemulsions, the particle diameter of which is far below 100 nm.
  • the PIT emulsions have a brown-red appearance when viewed through and bluish shimmering in reflected light, which is explained by the Tynda11 scatter on the emulsion droplets.
  • the invention therefore relates to aqueous preparations of ionic surfactants containing emulsified fatty substances, the emulsified fatty substances in the form of a nonionic, finely divided emulsion with an average droplet diameter of 100-300 nm, which heats to phase inversion temperature during or after their preparation was present.
  • Ionic surfactants are understood here to mean all water-soluble surface-active substances which are distinguished by a preferably linear fatty alkyl or fatty acyl group and an anionic, zwitterionic, amphoteric or cationic group which causes water solubility.
  • All water-insoluble oils, fats and waxes of mineral, animal, vegetable and synthetic origin are understood as fatty substances. However, preference is given to those fatty substances or fatty substance mixtures whose melting point is below the phase inversion temperature of the emulsion, since the emulsions then do not have to be heated significantly above the phase inversion temperature range during production.
  • the phase inversion temperature of the PIT emulsion can be shifted to below 100 ° C. by selecting suitable emulsifiers. This is particularly advantageous because pressure can then be dispensed with when producing the PIT emulsion.
  • the preparations according to the invention can contain the ionic surfactants and the emulsified fatty substances in any proportions. For practical use, however, those preparations are preferred which:
  • Another particularly preferred object of the invention is therefore aqueous preparations of ionic surfactants which, as ionic surfactants, anionic, zwitterionic, amphoteric or cationic surfactants or mixtures thereof and additionally cationic softening additives from the group of
  • the cationic softening additives mentioned are preferably present in the preparations in amounts of 0.01-2.0% by weight.
  • the anionic surfactants used are alkyl sulfates and / or alkyl polyglycol ether sulfates having 10 to 18 carbon atoms in the alkyl group and up to 12 polyglycol ether groups and / or Alkyl polyglycol ether sulfosuccinic acid monoesters with 10-16 C atoms in the alkyl group and 2-6 glycol ether groups are used.
  • Suitable anionic surfactants for the production of hair treatment agents according to the invention are primary and secondary linear alkanesulfonates with 10 to 18 carbon atoms, alkene sulfonates and hydroxyalkanesulfonates, such as are obtained in the sulfonation of olefins with 10 to 18 carbon atoms, fatty acid alkylolamide - and fatty acid alkylolamide polyglycol ether sulfates, sulfated fatty acid monoglycerides, alkyl polyglycol ether carboxylates with 8-18 C atoms in the alkyl chain and 2-6 glycol ether groups, acyl sarcosines, acyl taurides and acyl isethionates with 8-18 C atoms in the acyl group.
  • the anionic surfactants mentioned can be in the form of the alkali metal, ammonium, alkanola monium salts, and the alkyl sulfates and alkyl polyglycol ether sulfates can also be in the form of the magnesium salts.
  • Zwitterionic surfactants are characterized by a lipophilic alkyl or acyl group with 8 - 18 C atoms, a quaternary ammonium group and a carboxyl group.
  • suitable zwitterionic surfactants are, for example, N- (Ci2-Ci8) - a ⁇ yl-N, N-dimethyl-glycinate, N- (C12-Ci8) -acylaminopropyl-N, N-dimethyl-glycinate, N- (Ci2- Ci8) -acyl-amino-ethyl-N, N-dimethyl-glycinate, - (Ci2 * - * Ci8) - a yl a ⁇ , i no P r ° pyl-N * -methyl-N-hydroxyethyl-glycinate, 2- (Ci2-Ci8) - a lkyl-l-carboxymethyl-3-hydroxylethyl-imi
  • Amphoteric surfactants are characterized by a lipophilic alkyl or acyl group, a protonatable amine group and a carboxyl group.
  • suitable amphoteric surfactants are, for example, N- (Ci2-CisJ-alkylaminoacetic acid, N- (Ci2-Ci8) -acylaminopropyl-aminopropionic acid.
  • Amine oxide surfactants can be used in the preparations according to the invention instead of a photic surfactants.
  • Suitable amine oxide surfactants are, for example, lauryl-diethylamine oxide or cocoalkyl- (Ci2-Ci8) -dimethylamine oxide.
  • Cationic surfactants are characterized by at least one lipophilic alkyl or acyl group and a protonatable amino group or a quaternary ammonium group.
  • the amino or ammonium group can also be part of a heterocyclic ring, e.g. a pyridine or imidazoline ring.
  • Cationic surfactants which carry only a lipophilic alkyl, hydroxyalkyl or acyloxyalkyl group and which are soluble in aqueous media at normal temperature (20 ° C.) to at least 1% by weight are particularly suitable.
  • quaternary ammonium compounds which have limited water solubility, i.e. which are only dispersible in water at room temperature.
  • Such quaternary ammonium compounds are e.g. by two or three long-chain alkyl, acyloxyalkyl or acylamidoalkyl groups, each with 12-22 carbon atoms.
  • a preferred example of such a quaternary ammonium compound is e.g. the di- (oleoyloxyethylJ-hydroxyethyl-methyl-ammonium chloride.
  • the oleoyl residue there can also be a saturated fatty acyl residue with 16-22 carbon atoms or an acyl residue from a natural fatty acid mixture, e.g. palm oil fatty acid or tallow fatty acid.
  • Cationic polymers suitable as cationic softening additives are water-soluble natural or synthetic polymers which carry amino groups or quaternary ammonium groups in the polymer chain or bound to it.
  • cationic polymers are, for example, ceilulose ethers modified with epoxypropyl-trimethyl-ammonium chloride and under trade names such as polymer JR are in the trade.
  • cationically modified guar gums are commercially available with the names Jaguar C 13 or Cosmedia Guar C 261.
  • cationic polymers which can be used according to the invention are e.g. the quaternized copolymers of vinyl pyrrolidone and dialkylamino alkyl acrylate (or methacrylate), which are available, for example, under the trade name Gafquat 734 or Gafquat 755.
  • Other suitable cationic polymers are the poly-dimethyldiallylammonium chloride, which is commercially available under the name Merquat 100.
  • Cationic polymers which are commercially available under the name Mirapol A 15 or poly- [N- (3-dimethylammonio) propyl] -N '- [3- (ethyleneoxyethylene dimethylammonio) propyl -] - urea dichloride are also suitable are.
  • Mirapol A 15 or poly- [N- (3-dimethylammonio) propyl] -N '- [3- (ethyleneoxyethylene dimethylammonio) propyl -] - urea dichloride are
  • the known zwitterionic polymers are also suitable, e.g. are accessible from polymers bearing amino groups by reaction with sodium chloroacetate, by copolymerization of anionic and cationic monomers or by polymerization of zwitterionic monomers. It is characteristic of the zwitterionic polymers that they carry more than one cationic group (e.g. amino or quaternary ammonium groups) and more than one anionic group (e.g. carboxyl or sulfonic acid groups) on the molecule. Mixtures of various cationic or zwitterionic polymers and quaternary ammonium compounds can of course also be used.
  • the polymers to be used according to the invention should be in solution, ie their water solubility should be at least 0.01% by weight at normal temperature (20 ° C.).
  • the aqueous preparations of ionic surfactants according to the invention are prepared by adding a finely divided (PIT) emulsion of a fatty substance with an average droplet diameter of to the aqueous solution of the ionic surfactant, which may already contain other water-soluble auxiliaries and additives 100-300 nm, which was heated to phase inversion temperature during or after its production, is added in such an amount that the preparation contains 0.01-10% by weight of the emulsified fat.
  • PIT finely divided
  • the PIT emulsion can contain both liquid oils and hydrocarbons such as paraffin oils, isohexadecane, 1,3-di-isooctylcyclohexane or synthetic ester oils, for example mono- and / or diesters of the formula (I) Rl-COOR 2 , (II ) R 2 00C-R 3 -C00R 3 and (III) RlCOO-R 3 - 00CR 2 , wherein R 1 and R 2 are alkyl groups with 1 - 22 C atoms or alkenyl groups with 8 - 22 C atoms and R 3 Alkylene groups with 2-16 carbon atoms and which contain at least 10 carbon atoms, contain natural or synthetic fatty acid triglycerides of fatty acids and 8-22 carbon atoms, and also contain paraffins and waxes which are semi-solid and solid at room temperature.
  • paraffin oils such as paraffin oils, isohexadecane, 1,3-di-iso
  • the PIT emulsions contain a combination of a hydrophobic, nonionic emulsifier with an HLB value of preferably 10-15 and a lipophilic co-emulsifier with an HLB value below 5.
  • the HLB value is to be understood as a size , which can be calculated from the structure of the emulsifier according to
  • HLB where L is the weight fraction (in%) of the lipophilic groups, for example the fatty alkyl or fatty acyl groups in the emulsifier.
  • the hydrophilic emulsifiers are preferably ethylene oxide adducts on fatty alcohols with 16-22 C atoms or on partial esters of polyols with 3-6 C atoms and fatty acids with 14-22 C atoms.
  • ethylene oxide addition products on fatty acids, on alkyl glucosides, on methyl glucoside fatty acid esters, on fatty acid alkanolamides, on fatty acid glucamides and other fatty substances with ethoxylatable substituents are also suitable.
  • alkyl polyglycosides of formula RO - (Z) x employ, in which R is a Cg_22- A lk l oc * er alkenyl group, Z is a monosaccharide, in particular glucose, and x is a number from 1.1 to 5, in particular from 1.2 to 1.4.
  • the lipophilic co-emulsifiers are preferably saturated fatty alcohols with 16-22 C atoms or free fatty acids with 16-22 C atoms, partial esters of polyols with 3-6 C atoms with saturated fatty acids with 14-22 C Atoms, e.g. Glycerol or sorbitan monofatty acid esters, glycol monofatty acid esters, fatty acid alkanolamides from Ci2-Ci8 fatty acids with mono- or dialkanolamines with 2-4 C atoms in the alkanol group or glycerol mono-fatty alcohol ethers.
  • the PIT emulsions are preferred to produce only with nonionic emulsifiers.
  • small amounts of ionic surfactants can also be incorporated, in amounts that do not interfere with the phase inversion.
  • To prepare preparations according to the invention containing cationic softening additives it may be advantageous to incorporate these softening additives into the PIT emulsion. In this way, a very valuable aid is obtained for the production of such preparations according to the invention.
  • a further subject of the invention is therefore an aid for the production of a preparation according to the invention in the form of a water-in-oil emulsion which was heated to phase inversion temperature during or after its production, and
  • the cationic softening additives are preferably added to the PIT emulsion after phase inversion, ie after cooling. Small Smaller amounts of these cationic additives, which do not interfere with the phase inversion of the system, can already be incorporated in the production of the PIT emulsion. Examples of such PIT emulsions are given in Nos. 1.5 to 1.12.
  • the PIT emulsion obtained in this way is particularly suitable for the preparation of the preparations according to the invention with cationic additives by adding them to the aqueous solution of the ionic surfactants in an amount such that 0.01-10% by weight in the preparation of the emulsified fat and 0.01-2% by weight of the cationic softening additives are included.
  • the nonionic surfactants are preferably introduced into the preparations according to the invention together with the PIT emulsions. Small amounts, i.e. Approx. 1-5% by weight, based on the entire preparation, can, however, also be introduced into the preparation with the ionic surfactants.
  • the known cationic surfactants e.g. Quaternary ammonium, pyridini or imidazolinium compounds with at least one, possibly also two, long-chain alkyl, acyloxyalkyl, hydroxyalkyl or acyl idoalkyl groups, each with 12-22 carbon atoms, alone or in combination with zwitterionic or a photeren Contain surfactants.
  • ionic surfactants When used as shampoos or shower preparations, ionic surfactants preferably contain highly foaming, anionic surfactants or combinations of anionic and zwitterionic or amphoteric surfactants. This also applies to the use as a manual dishwashing detergent or as a household cleaner or wool detergent.
  • the preparations according to the invention can contain further customary additives which are helpful for the particular application. It is only necessary to ensure that these additives do not interfere with the finely divided nature of the emulsified fatty substances and thus the effectiveness and storage stability.
  • thickening should be achieved with other substances, for example with nonionogenic water-soluble polymers such as hydroxyethyl cellulose, xanthan gum, polyvinylpyrrolidone, polyethylene oxides or polyethylene glycol stearate.
  • the PIT emulsions 1.1 to 1.16 were prepared by heating all components together in a water bath to the manufacturing temperature, mixing, emulsifying and cooling to room temperature from 20 ° C. (with stirring). The manufacturing temperature was above or within the phase inversion temperature range. Emulsion 1.15 shows an excessively large average particle size and is used for comparison (in Example 2.6).
  • Formaldehyde (37%) 0.15 0.15 0.15 0.15 0.15 0.15 0.15
  • the shampoo 2.6 was produced for comparison with a coarse-particle macro emulsion (emulsion 1.15) and shows only a slight improvement in wet combability.
  • the comparative value (S) was obtained when a 14% aqueous solution of fatty alcohol - Ci2-i4-poly- (2 E0) -glycol ether sulfate, Na salt was used as the test shampoo. This value is approx. 65 mJ (NK **** 100%).
  • the combing resistance was measured, i.e. the force required to pull a measuring comb through the strands of hair.
  • the mean of the working integrals of the 20 strands of hair treated with each test shampoo was formed.
  • the measurement was carried out in an automatic wet combability measuring apparatus, which essentially consisted of a robot-assisted sample changer and a strain gauge force transducer. The measured values were recorded electronically and evaluated using a computer.
  • Texapon N 25 fatty alcohol-Ci2-i4-poly- (2 E0) - and glycol ether sulfate, Na salt,
  • Dehyquart E N- (2-hydroxyhexadecy1) -N- (2-hydroxyethyl) dimethyl ammonium chloride (30% solution)
  • Dehyquart AU 56 RC-0CH 2 -CH 2 - - CH 2 -CH 2 -0-CR Cl-
  • RCO palm oil fatty acyl
  • Polyampholyte 3033 copolymer of methacrylamido-propyl-trimethylammonium chloride and acrylic acid (7: 3), neutralized with sodium hydroxide solution.
  • Cetiol 0E di-n-octyl ether Eumulgin Bl: cetyl / stearyl alcohol poly (12E0) - glycol ether (Ceteareth-12)
  • Arlypon F Lauryl / myristyl alcohol poly (2.5 E0) glycol ether
  • Dehyton K coconut acylamidopropyl dimethylglycerol
  • Plantaren 1200 alkyl (Ci2) glucoside (50% in water)
  • Benecel MP-945 methyl hydroxyprop 1ce11u1ose

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Abstract

On améliore les effets de compositions aqueuses d'agents tensioactifs ioniques sur des surfaces kératiniques par l'adjonction de matières grasses émulsionnées sous forme d'une émulsion finement dispersée non ionique ayant des gouttelettes d'un diamètre moyen compris entre 100 et 300 nm. Cette émulstion est chauffée pendant ou après sa préparation jusqu'à la température d'inversion de phases. Le dessèchement de la peau, notamment, est réduit, la peignabilité des cheveux mouillés est améliorée et le séchage des cheveux est accéléré.
PCT/EP1994/001653 1993-06-01 1994-05-24 Compositions tensioactives aqueuses WO1994027570A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP7500205A JPH08511292A (ja) 1993-06-01 1994-05-24 水性界面活性剤製剤
EP94918356A EP0701432A1 (fr) 1993-06-01 1994-05-24 Compositions tensioactives aqueuses

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19934318171 DE4318171A1 (de) 1993-06-01 1993-06-01 Wäßrige tensidische Zubereitungen
DEP4318171.6 1993-06-01

Publications (1)

Publication Number Publication Date
WO1994027570A1 true WO1994027570A1 (fr) 1994-12-08

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EP (1) EP0701432A1 (fr)
JP (1) JPH08511292A (fr)
DE (1) DE4318171A1 (fr)
WO (1) WO1994027570A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996016147A1 (fr) * 1994-11-17 1996-05-30 Henkel Kommanditgesellschaft Auf Aktien Dispersions aqueuses de cire
US6555100B1 (en) 1997-12-31 2003-04-29 L'ORéAL S.A. Compositions for treating keratinous materials containing a combination of a zwitterion polymer and a water insoluble non-volatile silicon
US8940282B2 (en) 2008-02-11 2015-01-27 The Procter & Gamble Company Process for reducing hair damage upon treatment of hair by heat
US9427603B2 (en) 2008-02-11 2016-08-30 The Procter & Gamble Company Process for reducing hair damage upon treatment of hair by heat
US9585497B2 (en) 2011-09-30 2017-03-07 The Procter & Gamble Company Modular display system

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DE19532542B4 (de) * 1995-09-04 2008-12-18 Henkel Ag & Co. Kgaa Klarspülmittel mit kationischen Polymeren
FR2745716B1 (fr) 1996-03-07 1998-04-17 Oreal Emulsions huile-dans-eau moussantes pressurisables ultrafines
DE19710149A1 (de) 1997-03-12 1998-09-17 Henkel Kgaa Körperreinigungsmittel
DE19719504C1 (de) 1997-05-12 1998-12-10 Henkel Kgaa Verfahren zur Herstellung von Haarfärbemitteln
DE19837841A1 (de) * 1998-08-20 2000-02-24 Cognis Deutschland Gmbh Verwendung von wäßrigen Wachsdispersionen als Konsistenzgeber
DE102004061610A1 (de) * 2004-12-17 2006-06-22 Henkel Kgaa Kosmetisches Kit zur Haar-und Kopfhautbehandlung
FR2883474B1 (fr) * 2005-03-25 2009-04-24 Oreal Emulsion h/e moussante et son utilisation dans le domaine cosmetique
FR2883475A1 (fr) * 2005-03-25 2006-09-29 Oreal Emulsion h/e moussante et son utilisation dans le domaine cosmetique
FR2930436B1 (fr) * 2008-04-28 2010-06-11 Oreal Composition cosmetique comprenant une emulsion obtenue par un procede pit
FR2930442B1 (fr) * 2008-04-28 2010-06-11 Oreal Composition cosmetique comprenant une emulsion obtenue par procede pit
DE102010021688A1 (de) 2010-05-27 2011-12-01 Qineva Gmbh & Co. Kg Verfahren zur Herstellung eines micellaren Wirkstoffkonzentrats

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EP0217250A2 (fr) * 1985-09-28 1987-04-08 Henkel Kommanditgesellschaft auf Aktien Préparations moussantes tensio-actives ayant des composants huileux insolubles dans l'eau, solubilisés clairement
DE4010393A1 (de) * 1990-03-30 1991-10-02 Henkel Kgaa Verfahren zur herstellung von oel-in-wasser-cremes
WO1992001508A1 (fr) * 1990-07-16 1992-02-06 Henkel Kommanditgesellschaft Auf Aktien Emulsions huile-eau
EP0490053A1 (fr) * 1990-12-07 1992-06-17 Wella Aktiengesellschaft Composition de traitement des cheveux sous forme de microémulsion
WO1993009761A1 (fr) * 1991-11-22 1993-05-27 Richardson-Vicks Inc. Compositions combinees de nettoyage et d'hydratation de la peau

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Publication number Priority date Publication date Assignee Title
EP0217250A2 (fr) * 1985-09-28 1987-04-08 Henkel Kommanditgesellschaft auf Aktien Préparations moussantes tensio-actives ayant des composants huileux insolubles dans l'eau, solubilisés clairement
DE4010393A1 (de) * 1990-03-30 1991-10-02 Henkel Kgaa Verfahren zur herstellung von oel-in-wasser-cremes
WO1992001508A1 (fr) * 1990-07-16 1992-02-06 Henkel Kommanditgesellschaft Auf Aktien Emulsions huile-eau
EP0490053A1 (fr) * 1990-12-07 1992-06-17 Wella Aktiengesellschaft Composition de traitement des cheveux sous forme de microémulsion
WO1993009761A1 (fr) * 1991-11-22 1993-05-27 Richardson-Vicks Inc. Compositions combinees de nettoyage et d'hydratation de la peau

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996016147A1 (fr) * 1994-11-17 1996-05-30 Henkel Kommanditgesellschaft Auf Aktien Dispersions aqueuses de cire
US6555100B1 (en) 1997-12-31 2003-04-29 L'ORéAL S.A. Compositions for treating keratinous materials containing a combination of a zwitterion polymer and a water insoluble non-volatile silicon
US8940282B2 (en) 2008-02-11 2015-01-27 The Procter & Gamble Company Process for reducing hair damage upon treatment of hair by heat
US9427603B2 (en) 2008-02-11 2016-08-30 The Procter & Gamble Company Process for reducing hair damage upon treatment of hair by heat
US9585497B2 (en) 2011-09-30 2017-03-07 The Procter & Gamble Company Modular display system

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DE4318171A1 (de) 1994-12-08
EP0701432A1 (fr) 1996-03-20
JPH08511292A (ja) 1996-11-26

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