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WO1992001508A1 - Emulsions huile-eau - Google Patents

Emulsions huile-eau Download PDF

Info

Publication number
WO1992001508A1
WO1992001508A1 PCT/EP1991/001272 EP9101272W WO9201508A1 WO 1992001508 A1 WO1992001508 A1 WO 1992001508A1 EP 9101272 W EP9101272 W EP 9101272W WO 9201508 A1 WO9201508 A1 WO 9201508A1
Authority
WO
WIPO (PCT)
Prior art keywords
oil
weight
emulsifier
mono
emulsions
Prior art date
Application number
PCT/EP1991/001272
Other languages
German (de)
English (en)
Inventor
Marianne Waldmann-Laue
Irina Slominski
Werner Schneider
Karlheinz Hill
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
Zucker Aktiengesellschaft Uelzen-Braunschweig
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, Zucker Aktiengesellschaft Uelzen-Braunschweig filed Critical Henkel Kommanditgesellschaft Auf Aktien
Publication of WO1992001508A1 publication Critical patent/WO1992001508A1/fr

Links

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
    • A61K8/062—Oil-in-water 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/608—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/017—Mixtures of compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/017—Mixtures of compounds
    • C09K23/018—Mixtures of two or more different organic oxygen-containing compounds

Definitions

  • the invention relates to oil-in-water emulsions, in particular topical cosmetic and pharmaceutical preparations in the form of O / emulsions with improved emulsion stability.
  • emulsifiers for converting water-insoluble oil components into the form of aqueous emulsions are known. It is known that such emulsions with water or an aqueous solution as an outer, continuous phase with relatively hydrophilic emulsifiers, e.g. can be prepared with ionic (anionic, cationic, zwitterionic or amphoteric) and with nonionic emulsifiers which have good water solubility. It is also known that, in order to improve the stability of the emulsion, additional, less hydrophilic, nonionic compounds which themselves are hardly water-soluble but carry a polar group can be used. Such so-called co-emulsifiers are e.g. Fatty alcohols with 16 to 22 carbon atoms, fatty acid partial esters of glycols or polyols with 3 to 10 carbon atoms or fatty acid alkanolamides.
  • the known co-emulsifiers are not always suitable for improving the emulsion stability, so that the development of a stable emulsion very often requires a great deal of work in order to find a suitable emulsifier-co-emulsifier pair.
  • DE-A-24 61 316 describes the preparation of di- and tri-l- (2,7-octadienyl) ethers of tri ethyl propane. If one telomerizes butadiene or isoprene in the presence of mono- or disaccharides or in the presence of alkyl (C 1 -C 4) -glucosides, mixtures of sugar ethers are obtained under suitable conditions in high yields, which consist predominantly of mono-, di- and higher substituted octadienyl or dimethyloctadienyl ethers of these polyols exist (cf. J. Prakt. Chemie, Volume 315, No. 6, 1973,
  • the products can be hydrogenated to the corresponding octyl and diethyl octyl ethers.
  • sugar ethers are particularly suitable as co-emulsifiers for the preparation of oil-in-water emulsions and lead to emulsions which have superior stability even at elevated temperatures.
  • the invention therefore relates to emulsions of the oil-in-water type with a continuous aqueous phase and a discontinuous oil phase which, as an emulsifier, comprise a combination of a known, hydrophilic ionic emulsifier or a nonionic emulsifier with an HLB value of at least 10 a sugar ether of the general formula I
  • Z is the residue of a mono- or disaccharide or an alkyl glycoside of a mono- or disaccharide with an alkyl group of 1 to 4 carbon atoms
  • R is an octadienyl, dimethyloctadienyl, octyl or dimethyloctyl group bonded to an oxygen atom and the middle group Degree of substitution n - 1 to x, where x is the number of hydroxyl groups of the mono- or disaccharide or the alkyl glycoside.
  • the octadienyl group consists predominantly of the 1-octadiene (2,7) -yl and the 3-0ctadiene (1,7) -yl group.
  • the diethyl octadienyl groups formed by isoprene dimerization consist of isomers not previously identified.
  • the oil-in-water type emulsions according to the invention are understood to be both liquid O / W emulsions and O / W emulsion creams.
  • the continuous, outer aqueous phase contains water and the components which are readily soluble in water.
  • the dispersed oil phase consists of the oil components, the
  • oils known for topical cosmetic or pharmaceutical preparations can be included as oil components.
  • oils include: olive oil, sunflower oil, soybean oil, corn oil, peanut oil, turnip oil, castor oil, jojoba oil, sperm oil, mink oil, paraffin oils, silicone oils, squalane, 2-0ctyl-dodecanol, decyl oleate, isopropyl stearate, isononyl stearate, 2-ethyl-hexyl palmitate, glycerol tricaprylate and other esters and hydrocarbons known as cosmetic oil components. All known products with melting points up to approx. 80 ° C are suitable as cosmetic fats and waxes.
  • Vaseline hardened vegetable and animal fats (triglycerides), walrus, esters such as cetyl palmitate and natural waxes such as e.g. Beeswax, japan wax, carnauba wax, candeli ilaw wax, wool wax, mineral waxes, e.g. Montan waxes, paraffins, and polyethylene waxes.
  • the dispersed oil phase can also contain oil-soluble fat components with polar groups, such as have long been known as co-emulsifiers, such as e.g. Fatty alcohols with 16 to 22 carbon atoms, in particular cetyl and / or stearyl alcohol, fatty acid mono- and diglycerides, e.g. Glycerin onostearate, fatty acid monoethanol and ide and propylene glycol mono fatty acid ester, sorbitan fatty acid partial ester, methyl 1ucoside mono fatty acid ester.
  • co-emulsifiers such as e.g. Fatty alcohols with 16 to 22 carbon atoms, in particular cetyl and / or stearyl alcohol, fatty acid mono- and diglycerides, e.g. Glycerin onostearate, fatty acid monoethanol and ide and propylene glycol mono fatty acid ester, sorbitan fatty acid partial ester, methyl 1ucoside mono fatty acid ester.
  • the known anionic emulsifiers can be used as the hydrophilic emulsifier component, for example the soaps of fatty acids having 12 to 22 carbon atoms, the salts of phosphoric acid mono- and dialkyl (Ci2-Ci8-) esters, the salts of sulfuric acid monoesters of Ci2- C22-f r ettalko noir or an ⁇ particular anionic surfactants, in particular those which are anhydrous and li ⁇ -linear alkyl groups having 16 to 22 carbon atoms carry.
  • hydrophilic emulsifiers can also be used as hydrophilic emulsifiers for the purposes of the present invention if they have a hydrophilic, ionic group, for example a quaternary ammonium group, a betaine group or an aminocarboxylate group and in each case one
  • REPLACEMENT LEAF contain lipophilic, linear alkyl or alkenyl group with 12 to 22 carbon atoms.
  • nonionic emulsifiers which are obtained by adding ethylene oxide to fatty substances containing hydroxyl groups are preferably used as hydrophilic emulsifiers.
  • hydrophilic, nonionic emulsifiers are addition products of ethylene oxide onto, for example:
  • the amount of ethylene oxide added should be so high that the hydrophilicity of these emulsifiers corresponds to an HLB value (hydrophilic-lipophilic balance) of at least 10.
  • HLB value hydrophilic-lipophilic balance
  • a nonionic emulsifier with an HLB value of 10 to 18 is preferred.
  • the HLB value should be defined as
  • L is the weight fraction of the lipophilic group, e.g. the fatty alkyl or fatty acyl group, in% by weight of the ethylene oxide adduct.
  • the emulsions according to the invention contain, as the emulsifier combination, a mixture of 0.5 to 9 parts by weight of a hydrophilic nonionic emulsifier with an HLB value of 10 to 18 and 1 part by weight of a sugar ether of the general formula I.
  • REPLACEMENT LEAF Adaptation of the emulsifier to the oil component can be advantageous if the oil phase also contains a portion of a conventional co-emulsifier, for example cetyl / stearyl alcohol or glycerol mono- / distearate.
  • a conventional co-emulsifier for example cetyl / stearyl alcohol or glycerol mono- / distearate.
  • a particularly preferred emulsifier combination for carrying out the present invention therefore consists of a mixture of 0.5 to 9 parts by weight of a hydrophilic nonionic emulsifier with an HLB value of 10 to 18, 1 part by weight of a sugar ether of the formula I and, if appropriate up to 2 parts by weight of a linear, saturated fatty alcohol having 14 to 22 carbon atoms (for example cetyl or stearyl alcohol) or a fatty acid partial ester of a fatty acid having 14 to 22 carbon atoms and a glycol or polyol having 3 to 10 carbon atoms.
  • suitable fatty acid partial esters are glycerol mono / distearate, sorbitan mono- or sesquistearate, methyl glucoside sesquistearate or glucose monostearate.
  • water-soluble surfactants e.g., water-soluble sulfate, glycerol, glycerol, glycerol, glycerol, glycerol, glycerol, glycerol, glycerol, glycerol, glycerol, glycerol, glycerol, glycerol, glycerol, glycerol, g., sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite, sodium metabisulfite
  • Preservatives such as p-hydroxybenzoic acid ester, phenoxyethanol, chlorhexidine digluconate, formaldehyde, salts of benzoic acid, dehydroacetic acid and sorbic acid.
  • water-soluble thickeners e.g. Hydroxyethyl cellulose, carboxy ethyl cellulose, polyvinyl alcohol, polyvinyl pyrrolidone, salts of acrylic acid and methacrylic acid poly eris Ober and copoly eris affection, water-soluble plant matter
  • glycols and polyols e.g. 1,2-propylene glycol, 5orbitol, methyl glucoside
  • water-soluble cosmetic or pharmaceutical active ingredients e.g. water-soluble plant extracts, proteins and protein derivatives, amino acids
  • - water-soluble buffer substances e.g. Citrates, phosphates, borate.
  • the aqueous phase can also contain inorganic swelling agents and thickening agents such as swelling clays, finely divided silicas (Aerosil), talc (magnesium silicate) or magnesium aluminum silicates (eg Veegu ( R )).
  • inorganic swelling agents and thickening agents such as swelling clays, finely divided silicas (Aerosil), talc (magnesium silicate) or magnesium aluminum silicates (eg Veegu ( R )).
  • antioxidants e.g. tocopherols, butylated hydroxytoluene, etc.
  • oil-soluble, pharmaceutical and cosmetic active ingredients are dissolved in the oil phase of the emulsions according to the invention.
  • O / W emulsions according to the invention are expediently prepared as follows:
  • the oil components, fats and waxes are mixed with the emulsifier combination according to the invention and heated until a homogeneous melt is reached.
  • the water-soluble components are dissolved in water and, preferably at a temperature of 60 to 100 ° C., combined with the organic phase with mixing.
  • Water-soluble thickeners, water-dispersible swelling substances and water-sensitive water-soluble active substances are dissolved or dispersed separately in part of the water phase and mixed with the emulsion after cooling.
  • the mixing processes when emulsifying the oil and water phase or when subsequently mixing in aqueous solutions are preferably carried out using suitable mixing and emulsifying tools, e.g. of Spalth homogenizers, ultrasonic homogenizers or dynamic mixers
  • the emulsion has a phase inversion in the temperature range below 100 ° C., it is advantageous to produce the emulsion above this phase inversion temperature - or to heat it briefly over this temperature range - and then to cool it down to room temperature. This measure enables particularly fine-particle, low-viscosity and still highly stable oil-in-water emulsions to be obtained.
  • Cutina ( R ) KD 16 glycerol mono- / distearate / palmitate (Henkel)
  • the preparation was carried out analogously to a) using 832 g (15.4 mol) of butadiene.
  • the mean degree of substitution n was 1.5.
  • the preparation was carried out analogously to a), starting from 510 g (1.488 mol) of sucrose and 1340 g (24.81 mol) of 1.3 butadiene. A mixture of sucrose octadienyl ethers with an average degree of substitution of 5.5 was obtained.
  • the product had the following key figures:
  • REPLACEMENT LEAF 2 Testing the stability of the O / W emulsion No. 1 using the sugar ethers a, b, c, d (emulsion No. la, lb, lc, ld).

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

Abstract

Des émulsions du type huile-eau contiennent comme émulsifiant une combinaison d'un émulsifiant hydrophile connu, ionique ou non-ionique, ayant un équilibre hydrophile-lipophile d'au moins 10, avec un sucro-éther de formule générale (I): [Z]-(R)n où Z signifie le radical d'un mono- ou disaccharide ou d'un glycoside d'alkyle C1-C4 d'un mono- ou disaccharide, et R un groupe octadiényle, diméthyloctadiényle, octyle ou diméthyloctyle lié à un atome d'oxygène, et où le degré de substitution moyen n = 1 à x, x étant l'indice hydroxyle du mono- ou disaccharide ou du glycoside d'alkyle, comme coémulsifiant. Des coémulsifiants appropriés de formule (I) sont p.ex. l'éther d'octadiényle de glucose ayant un degré de substitution de n = 1 à 3, ou l'éther d'octadiényle de saccharose ayant un degré de substitution de 2 à 6.
PCT/EP1991/001272 1990-07-16 1991-07-08 Emulsions huile-eau WO1992001508A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4022540.2 1990-07-16
DE4022540A DE4022540A1 (de) 1990-07-16 1990-07-16 Oel-in-wasser-emulsionen

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WO1992001508A1 true WO1992001508A1 (fr) 1992-02-06

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0579455A1 (fr) * 1992-07-14 1994-01-19 Dow Corning Corporation Emulsion siliconée à usage corporel
WO1994016668A1 (fr) * 1993-01-23 1994-08-04 Henkel Kommanditgesellschaft Auf Aktien Emulsions moussantes
WO1994027570A1 (fr) * 1993-06-01 1994-12-08 Henkel Kommanditgesellschaft Auf Aktien Compositions tensioactives aqueuses
WO1995003881A1 (fr) * 1993-07-27 1995-02-09 Imperial Chemical Industries Plc Compositions a base de tensioactifs
EP0646368A1 (fr) * 1993-10-04 1995-04-05 L'oreal Composition d'organopolysiloxane d'aspect gélifié, sans gélifiant, utilisable en cosmétique et dermatologie
EP0647443A1 (fr) * 1993-10-08 1995-04-12 L'oreal Emulsion huile-dans-eau utilisable pour l'obtention d'une crème
WO1995031957A1 (fr) * 1994-05-19 1995-11-30 Henkel Kommanditgesellschaft Auf Aktien Micro-emulsions
WO1996000010A1 (fr) * 1994-06-24 1996-01-04 Zeneca Limited Composition herbicide
WO1997023192A1 (fr) * 1995-12-21 1997-07-03 Henkel Kommanditgesellschaft Auf Aktien Micro-emulsions huile dans eau contenant des agents tensioactifs saccharins et leur procede de preparation
EP0821949A2 (fr) * 1996-08-02 1998-02-04 Beiersdorf Aktiengesellschaft Composition moussante ou sous forme de mousse contenant des tensioactifs et des électrolytes
DE19643063A1 (de) * 1996-10-18 1998-04-23 Henkel Kgaa Kosmetische Zubereitungen in Stiftform
EP1752137A3 (fr) * 2005-08-02 2008-02-13 Merz Pharma GmbH & Co.KGaA Bases et compositions hydophiles ou ambiphiles

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19529907A1 (de) * 1995-08-15 1997-02-20 Henkel Kgaa Feinteilige Emulsionen enthaltend Zuckertenside
US5939081A (en) * 1996-02-27 1999-08-17 Henkel Kommanditgesellschaft Auf Aktien Esters of alkyl and/or alkenyl oligoglycosides with fatty acids
DE19607977A1 (de) * 1996-03-01 1997-09-04 Henkel Kgaa Verwendung von Emulgatormischungen
DE19738865A1 (de) * 1997-09-05 1999-03-11 Henkel Kgaa Verwendung von Estern von Alkyl- und/oder Alkenyloligoglykosiden mit Fettsäuren mit 6 bis 22 Kohlenstoffatomen als Emulgatoren

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4006192A (en) * 1973-12-27 1977-02-01 Kureha Kagaku Kogyo Kabushiki Kaisha 1,1-Di-(2,7 octadieneoxymethylene)-1-(hydroxymethylene)alkane
EP0141732A2 (fr) * 1983-10-25 1985-05-15 L'oreal Composition cosmetique de nettoyage en particulier pour le démaquillage des yeux
EP0268992A2 (fr) * 1986-11-28 1988-06-01 Henkel Kommanditgesellschaft auf Aktien Concentrés nacrés fluidisables
EP0282863A2 (fr) * 1987-03-14 1988-09-21 Henkel Kommanditgesellschaft auf Aktien Concentrés de nettoyage liquides alcalins

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4006192A (en) * 1973-12-27 1977-02-01 Kureha Kagaku Kogyo Kabushiki Kaisha 1,1-Di-(2,7 octadieneoxymethylene)-1-(hydroxymethylene)alkane
EP0141732A2 (fr) * 1983-10-25 1985-05-15 L'oreal Composition cosmetique de nettoyage en particulier pour le démaquillage des yeux
EP0268992A2 (fr) * 1986-11-28 1988-06-01 Henkel Kommanditgesellschaft auf Aktien Concentrés nacrés fluidisables
EP0282863A2 (fr) * 1987-03-14 1988-09-21 Henkel Kommanditgesellschaft auf Aktien Concentrés de nettoyage liquides alcalins

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0579455A1 (fr) * 1992-07-14 1994-01-19 Dow Corning Corporation Emulsion siliconée à usage corporel
US5656200A (en) * 1993-01-23 1997-08-12 Henkel Kommanditgesellschaft Auf Aktien Foaming emulsions
WO1994016668A1 (fr) * 1993-01-23 1994-08-04 Henkel Kommanditgesellschaft Auf Aktien Emulsions moussantes
WO1994027570A1 (fr) * 1993-06-01 1994-12-08 Henkel Kommanditgesellschaft Auf Aktien Compositions tensioactives aqueuses
WO1995003881A1 (fr) * 1993-07-27 1995-02-09 Imperial Chemical Industries Plc Compositions a base de tensioactifs
US6586366B1 (en) 1993-07-27 2003-07-01 Imperial Chemical Industries Plc Homogenous agrochemical concentrates and agrochemical formulations obtained therefrom
EP0646368A1 (fr) * 1993-10-04 1995-04-05 L'oreal Composition d'organopolysiloxane d'aspect gélifié, sans gélifiant, utilisable en cosmétique et dermatologie
FR2710843A1 (fr) * 1993-10-04 1995-04-14 Oreal Composition d'organopolysiloxane d'aspect gélifié, sans gélifiant, utilisable en cosmétique et dermatologie.
EP0647443A1 (fr) * 1993-10-08 1995-04-12 L'oreal Emulsion huile-dans-eau utilisable pour l'obtention d'une crème
FR2710854A1 (fr) * 1993-10-08 1995-04-14 Oreal Emulsion huile-dans-eau utilisable pour l'obtention d'une crème.
WO1995031957A1 (fr) * 1994-05-19 1995-11-30 Henkel Kommanditgesellschaft Auf Aktien Micro-emulsions
AU698255B2 (en) * 1994-06-24 1998-10-29 Syngenta Limited Herbicidal composition
EP0852113A2 (fr) * 1994-06-24 1998-07-08 Zeneca Limited Composition herbicide
US5888934A (en) * 1994-06-24 1999-03-30 Zeneca Limited Herbicidal compositions and adjuvant composition comprising alkylpolyglycoside and ethoxylated alcohol surfactants
EP0852113A3 (fr) * 1994-06-24 1999-10-20 Zeneca Limited Composition herbicide
WO1996000010A1 (fr) * 1994-06-24 1996-01-04 Zeneca Limited Composition herbicide
WO1997023192A1 (fr) * 1995-12-21 1997-07-03 Henkel Kommanditgesellschaft Auf Aktien Micro-emulsions huile dans eau contenant des agents tensioactifs saccharins et leur procede de preparation
EP0821949A2 (fr) * 1996-08-02 1998-02-04 Beiersdorf Aktiengesellschaft Composition moussante ou sous forme de mousse contenant des tensioactifs et des électrolytes
EP0821949A3 (fr) * 1996-08-02 1999-04-21 Beiersdorf Aktiengesellschaft Composition moussante ou sous forme de mousse contenant des tensioactifs et des électrolytes
DE19643063A1 (de) * 1996-10-18 1998-04-23 Henkel Kgaa Kosmetische Zubereitungen in Stiftform
EP1752137A3 (fr) * 2005-08-02 2008-02-13 Merz Pharma GmbH & Co.KGaA Bases et compositions hydophiles ou ambiphiles

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