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WO1999045893A1 - Utilisation d'alkylgalactomannanes - Google Patents

Utilisation d'alkylgalactomannanes Download PDF

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Publication number
WO1999045893A1
WO1999045893A1 PCT/EP1999/001288 EP9901288W WO9945893A1 WO 1999045893 A1 WO1999045893 A1 WO 1999045893A1 EP 9901288 W EP9901288 W EP 9901288W WO 9945893 A1 WO9945893 A1 WO 9945893A1
Authority
WO
WIPO (PCT)
Prior art keywords
alcohols
esters
fatty
linear
branched
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.)
Ceased
Application number
PCT/EP1999/001288
Other languages
German (de)
English (en)
Inventor
Achim Ansmann
Rolf Kawa
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.)
Henkel AG and Co KGaA
BASF Personal Care and Nutrition GmbH
Original Assignee
Henkel AG and Co KGaA
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
Application filed by Henkel AG and Co KGaA, Cognis Deutschland GmbH and Co KG filed Critical Henkel AG and Co KGaA
Publication of WO1999045893A1 publication Critical patent/WO1999045893A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • A61K8/064—Water-in-oil emulsions, e.g. Water-in-silicone emulsions
    • 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
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • 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
    • A61K2800/52—Stabilizers

Definitions

  • the invention relates to the use of special polyglucose ethers for the production of W / O emulsions.
  • the homogenization of the disperse phase is an important criterion for the uniform distribution of small droplets and thus for the stability and smooth structure of a W / O emulsion.
  • the duration and intensity of the homogenization depends on the existing machine conditions and, to a very large extent, also on the viscosity properties of the emulsion.
  • forced homogenization proves to be necessary since this is the only way to ensure that the entire emulsion actually passes through the homogenization zone. To produce stable and elegant W / O emulsions, it is therefore necessary to have a technically modern production facility available.
  • the invention relates to the use of alkyl lactomannans as interface stabilizers for the preparation of W / O emulsions.
  • alkylated galactomannans have the property of stabilizing W / O emulsions at the interfaces and at the same time distributing the disperse phase very finely and homogeneously without the need for a homogenization step.
  • the emulsions produced with such a polysaccharide structure have a very good storage stability and correspond to the homogenized W / O with regard to cosmetic requirements such as sensors and elegance.
  • the invention includes the knowledge that the alkylgalactomannans are also suitable for thickening oil preparations, ointments and stick formulations.
  • Alkylgalactomannans are alkyl ethers of (galacto) mannan and are commercially available, for example, from Aqualon under the brand N-Hance® AG50 and AG200. The use of these substances in sunscreens is also known from European patent application EP-A2 0804923 (L'Oreal). C1-C5 alkylgalactomannans are preferably used, the amount of stabilizers used being 0.1 to 5, preferably 0.5 to 3 and in particular 1 to 2% by weight, based on the emulsion.
  • TN linear or branched, symmetrical or asymmetrical dialkyl ethers with 6 to 22 carbon atoms per alkyl group, ring opening products of epoxidized fatty acid esters with polyols, silicone oils and / or aliphatic or naphthenic hydrocarbons.
  • the oil bodies are usually used in amounts of 5 to 25, preferably 10 to 20 and in particular 12 to 15% by weight, based on the emulsions.
  • Emulsifiers are usually used in amounts of 5 to 25, preferably 10 to 20 and in particular 12 to 15% by weight, based on the emulsions.
  • Suitable emulsifiers are nonionic surfactants from at least one of the following groups:
  • Ci2 / i8 fatty acid monoesters and diesters of addition products of 1 to 30 moles of ethylene oxide with glycerol;
  • alkyl mono- and oligoglycosides with 8 to 22 carbon atoms in the alkyl radical and their ethoxylated analogs
  • polyol and especially polyglycerol esters such as e.g. Polyglycerol polyricinoleate, polyglycerol poly-12-hydroxystearate or polyglycerol dimerate. Mixtures of compounds from several of these classes of substances are also suitable;
  • partial esters based on linear, branched, unsaturated or saturated C6 / 22 fatty acids, ricinoleic acid and 12-hydroxystearic acid and glycerin, polyglycerin, pentaerythritol, dipentaerythritol, sugar alcohols (e.g. sorbitol), alkyl glucosides (e.g. methyl glucoside, butyl glucoside - glucoside) and polygiucosides (eg cellulose);
  • the adducts of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters as well as sorbitan mono- and diesters of fatty acids or with castor oil are known, commercially available products. These are homolog mixtures, the middle of which Degree of alkoxylation corresponds to the ratio of the amounts of ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out.
  • Ci2 / i8 fatty acid monoesters and diesters of adducts of ethylene oxide with glycerol are known from DE-PS 20 24 051 as refatting agents for cosmetic preparations.
  • C ⁇ -alkyl mono- and oligoglycosides their preparation and their use are known from the prior art. They are produced in particular by reacting glucose or oligosaccharides with primary alcohols with 8 to 18 carbon atoms.
  • glycoside residue both monoglycosides in which a cyclic sugar residue is glycosidically bonded to the fatty alcohol and oligomeric glycosides with a degree of oligomerization of up to about 8 are suitable.
  • the degree of oligomerization is a statistical mean value which is based on a homolog distribution customary for such technical products.
  • Zwitterionic surfactants can also be used as emulsifiers.
  • Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines, such as the N-alkyl-N, N-dimethylammonium glycinate, for example coconut alkyldimethylammonium glycinate, N-acylamino propyl-N, N-dimethylammonium glycinate, for example coconut acylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxyl -3-hydroxyethylimidazoiine each with 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethyiglycinate.
  • betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example coconut alkyldimethylammonium glycinate, N-acylamino propyl-N, N-dimethylammonium gly
  • fatty acid amide derivative known under the CTFA name Cocamidopropyl Betaine is particularly preferred.
  • Suitable emulsifiers are ampholytic surfactants.
  • Ampholytic surfactants are surface-active compounds which, in addition to a C ⁇ m alkyl or acyl group, contain at least one free amino group and at least one -COOH or -SO3H group in the molecule and are capable of forming internal salts.
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids, each with about 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and Ci2 / i8-acylsarcosine.
  • quaternary emulsifiers are also suitable, those of the ester quat type, preferably methyl-quaternized difatty acid triethanolamine ester salts, being particularly preferred.
  • the emulsifiers are usually used in amounts of 0.1 to 10, preferably 1 to 8 and in particular 2 to 5% by weight, based on the emulsions. Auxiliaries and additives
  • the W / O emulsions can also contain, as further auxiliaries and additives, superfatting agents, pearlescent waxes, stabilizers, consistency enhancers, thickening agents, polymers, silicone compounds, biogenic active ingredients, antidandruff agents, film formers, preservatives, Contain hydrotropes, solubiiizers, UV light protection filters, insect repellents, self-tanners, perfume oils, dyes and the like.
  • Substances such as, for example, lanolin and lecithin and polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers.
  • Perlglan waxes include, for example: alkylene glycol esters, especially ethylene glycol distearate; Fatty acid alkanolamides, especially coconut fatty acid diethanolamide; Partial glycerides, especially stearic acid monoglyceride; Esters of polyvalent, optionally hydroxy-substituted carboxylic acids with fatty alcohols having 6 to 22 carbon atoms, especially long-chain esters of tartaric acid; Fatty substances, such as, for example, fatty alcohols, fatty ketones, fatty aldehydes, fatty ethers and fatty carbonates, which have a total of at least 24 carbon atoms, especially lauron and distearyl ether; Fatty acids such as stearic acid, hydroxystearic acid or behenic acid, ring opening products of olefin epoxides with 12 to 22 carbon atoms with fatty alcohols with 12 to 22 carbon atoms and / or polyols with 2 to 15 carbon
  • Suitable consistency agents are primarily fatty alcohols or hydroxy fatty alcohols with 12 to 22 and preferably 16 to 18 carbon atoms and, in addition, partial glycerides, fatty acids or hydroxy fatty acids.
  • a combination of these substances with alkyl oligoglucosides and / or fatty acid N-methylgiucamides of the same chain length and / or polyglycerol poly-12-hydroxystearates is preferred.
  • Suitable thickeners are, for example, polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, furthermore higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates (for example Carbopole® from Goodrich or Synthalene® from Sigma), polyacrylamides, polyvinyl alcohol and polyvinyl pyrrolidone, surfactants such as ethoxylated fatty acid glycerides, esters of fatty acids with polyols such as pentaerythritol or trimethylol propane, fatty alcohol ethoxylates with a narrow homolog distribution or alkyl oligoglucosides as well as electrolytes such as table salt and ammonium chloride.
  • polysaccharides in particular xanthan gum, guar guar, agar agar, algina
  • Suitable cationic polymers are, for example, cationic cellulose derivatives, such as, for example, a quaternized hydroxyethyl cellulose which is available under the name Polymer JR 400® from Amerchol, cationic starch, copolymers of diallylammonium salts and acrylamides, quaternized vinylpyrrolidone / vinylimidazole polymers, such as, for example, Luviquat® ( BASF), condensation products of polyglycols and amines, quaternized collagen polypeptides, such as lauryldimonium hydroxypropyl hydrolyzed collagen (Lamequat®L / Grünau), quaternized wheat polypeptides, polyethyleneimine, cationic silicone polymers such as amidomethicones, copolymers of adipic acid and dimethyldiethylenetriaminohydroxy (aminohydroxy) Cartaretine® / Sandoz), copolymers of acrylic acid with dimethyldiallylammoni
  • Ais anionic, zwitterionic, amphoteric and nonionic polymers are, for example, Vinyiacetat / crotonic acid copolymers, vinylpyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobornyl acrylate copolymers, Methylvinyiether / maleic anhydride copolymers and esters thereof, un- crosslinked and polyol-crosslinked polyacrylic acids, Acrylamidopropyltrimethylammoniurnchlorid / Acrylate copolymers, octylacrylamide / methyl methacrylate / tert.butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers, polyvinyl pyrrolidone, vinyl pyrrolidone / vinyl acetate copolymers, vinyl pyrrolidone / dimethylaminoethyl meth
  • Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, cyclic silicones and amino, fatty acid, alcohol, polyether, epoxy, fluorine, glycoside and / or alkyl-modified silicone compounds, which can be both liquid and resinous at room temperature.
  • Typical examples of fats are glycerides, beeswax, camamauba wax, candelilla wax, montan wax, paraffin wax or microwaxes, if appropriate in combination with hydrophilic waxes, for example cetylstearyl alcohol or partial glycerides.
  • Biogenic active substances are, for example, tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, deoxyribonucleic acid, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils, plant extracts and vitamin supplements.
  • Climbazole, octopirox and zinc pyrethione can be used as antidandruff agents.
  • Common film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone Vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid or its salts and similar compounds.
  • Montmorillonites, clay minerals, pemulene and alkyl-modified carbopol types can serve as swelling agents for aqueous phases.
  • UV light protection filters are organic substances which are able to absorb ultraviolet rays and the absorbed energy in the form of longer-wave radiation, e.g. To give off heat again.
  • UVB filters can be oil-soluble or water-soluble. As oil-soluble substances e.g. to call:
  • 3-benzylidene camphor and its derivatives e.g. 3- (4-Methylbenzyiiden) camphor;
  • 4-aminobenzoic acid derivatives preferably 2-ethylhexyl 4- (dimethylamino) benzoate, 2-octyl 4- (dimethylamino) benzoate and amyl 4- (dimethylamino) benzoate;
  • esters of cinnamic acid preferably 2-ethylhexyl 4-methoxycinnamate, 2-ethylhexyl 4-methoxycinnamate, 2-ethylhexyl 2-cyano-3-phenylcinnamate (octocrylene);
  • esters of salicylic acid preferably 2-ethylhexyl salicylate, 4-isopropylbenzyl salicylate, homomethyl salicylic acid;
  • benzophenone preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone;
  • esters of benzalmalonic acid preferably di-2-ethylhexyl 4-methoxybenzmalonate
  • Triazine derivatives e.g. 2,4,6-trianilino- (p-carbo-2'-ethyl-1'-hexyloxy) -1, 3,5-triazine and octyltriazone.
  • Propane-1,3-dione e.g. 1 - (4-tert-Butylphenyl) -3- (4'methoxyphenyl) propane-1, 3-dione.
  • Sulfonic acid derivatives of 3-benzyiide camphor e.g. 4- (2-oxo-3-bornyiidenemethyl) benzenesulfonic acid and 2-methyl-5- (2-oxo-3-bomylidene) sulfonic acid and their salts.
  • UV-A filters such as 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1, 3-dione or 1-phenyl-3-
  • UV-A filters 4'-isopropylphenyl) propane-1,3-dione.
  • the UV-A and UV-B filters can of course also be used in mixtures.
  • insoluble pigments namely finely dispersed metal oxides or salts, such as, for example, titanium dioxide, zinc oxide, iron oxide, aluminum oxide, cerium oxide, zirconium oxide, silicates (talc), barium sulfate and zinc stearate are also suitable for this purpose.
  • the Particles should have an average diameter of less than 100 nm, preferably between 5 and 50 nm and in particular between 15 and 30 nm. They can have a spherical shape, but it is also possible to use particles which have an ellipsoidal shape or shape which differs from the spherical shape in some other way.
  • secondary light stabilizers of the antioxidant type can also be used, which interrupt the photochemical reaction chain which is triggered when UV radiation penetrates the skin. Typical examples are superoxide dismutase, tocopherols (vitamin E) and ascorbic acid (vitamin C). Further suitable UV light protection filters can be found in the overview by P.Finkel in S ⁇ FW-Journal 122, 543 (1996).
  • Hydrotropes such as ethanol, isopropyl alcohol or polyols can also be used to improve the flow behavior.
  • Polyols that come into consideration here preferably have 2 to 15 carbon atoms and at least two hydroxyl groups. Typical examples are
  • Alkylene glycols such as, for example, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and polyethylene glycols with an average molecular weight of 100 to 1,000 daltons;
  • Methyl compounds such as in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol;
  • Lower alkyl glucosides in particular those with 1 to 8 carbons in the alkyl radical, such as methyl and butyl glucoside;
  • Sugar alcohols with 5 to 12 carbon atoms such as sorbitol or mannitol,
  • Aminosugars such as glucamine.
  • Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid and the other classes of substances listed in Appendix 6, Parts A and B of the Cosmetics Ordinance.
  • N, N-diethyl-m-touluamide, 1, 2-pentanediol or Insect repellent 3535 are suitable as insect repellents, and dihydroxyacetone is suitable as a self-tanner.
  • Perfume oils include mixtures of natural and synthetic fragrances. Natural fragrances are extracts of flowers (lily, lavender, roses, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, cumin, juniper), fruit peel (bergamot, lemon, Oranges), roots (mace, angelica, celery, cardamom, costus, iris, calmus), woods (pine, sandal, guaiac, cedar, rosewood), herbs and grasses (Tarragon, lemongrass, sage, thyme), needles and twigs (spruce, fir, pine, mountain pine), resins and balsams (galbanum, elemi, benzoin, myrrh, olibanum, opoponax).
  • Typical synthetic fragrance compounds are products of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type. Fragrance compounds of the ester type are, for example, benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethylbenzylcarbinylacetate, phenylethyl acetate, linalyl benzoate, benzyl formate, ethylmethyl-phenylgiycinate, allylcyclohexylproalylatepylate-benzylate-benzylate-benzylate-benzylate-benzylate.
  • the ethers include, for example, benzyl ethyl ether, the aldehydes, for example, the linear alkanals with 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamenaldehyde, hydroxycitronellal, lilial and bourgeonal, the ketones, for example, the jonones, ⁇ -isomethylionone and methyl cedryl ketone, the alcohols anethole, citronellol, eugenol, isoeugenol, geraniol, linalool, phenyiethyl alcohol and te ⁇ ineol, the hydrocarbons mainly include the terpenes and balsams.
  • fragrance oils of lower volatility which are mostly used as aroma components, are also suitable as perfume oils, e.g. sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon leaf oil, linden blossom oil, juniper berry oil, vetiver oil, oliban oil, galbanum oil, labolanumol and lavandin oil.
  • 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 emulsions.
  • the agents can be produced by customary cold or hot processes; the phase inversion temperature method is preferably used.
  • the non-aqueous fraction of the W / O emulsions is usually in the range from 10 to 50 and preferably 25 to 35% by weight.
  • Another object of the invention relates to a process for the preparation of W / O emulsions by mixing an aqueous and an oil-containing phase, which is characterized in that alkylgalactomannans are used as interface stabilizers and there is no homogenization step.
  • the avoidance of homogenization is to be understood in such a way that the formation of the emulsion spontaneously, i.e. takes place even with gentle stirring of the two phases and a strong shear is not necessary.
  • Polyglyceryl-2 dipolyhydroxystearate 3.0 3.0

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne l'utilisation d'alkylgalactomannanes comme stabilisants interfaciaux pour produire des émulsions eau-huile. Des préparations stables au stockage peuvent ainsi être obtenues sans étape d'homogénéisation.
PCT/EP1999/001288 1998-03-09 1999-02-27 Utilisation d'alkylgalactomannanes Ceased WO1999045893A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19810011.6 1998-03-09
DE19810011A DE19810011A1 (de) 1998-03-09 1998-03-09 Verwendung von Alkylgalactomannanen

Publications (1)

Publication Number Publication Date
WO1999045893A1 true WO1999045893A1 (fr) 1999-09-16

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Application Number Title Priority Date Filing Date
PCT/EP1999/001288 Ceased WO1999045893A1 (fr) 1998-03-09 1999-02-27 Utilisation d'alkylgalactomannanes

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DE (1) DE19810011A1 (fr)
WO (1) WO1999045893A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3061500A1 (fr) 2015-02-25 2016-08-31 Symrise AG Dispersions stables

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100560092B1 (ko) * 2000-12-15 2006-03-10 파트릭 프랑케 저알레르기성 및 비자극성 피부 보호 제제

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0795321A1 (fr) * 1996-03-12 1997-09-17 L'oreal Emulsion eau-dans-huile gelifée stable
JPH09301823A (ja) * 1996-05-10 1997-11-25 Sunstar Inc 油中水型乳化化粧料

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0795321A1 (fr) * 1996-03-12 1997-09-17 L'oreal Emulsion eau-dans-huile gelifée stable
JPH09301823A (ja) * 1996-05-10 1997-11-25 Sunstar Inc 油中水型乳化化粧料

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 098, no. 003 27 February 1998 (1998-02-27) *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3061500A1 (fr) 2015-02-25 2016-08-31 Symrise AG Dispersions stables

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Publication number Publication date
DE19810011A1 (de) 1999-09-16

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