WO1996028245A1 - Emulsions multiples eau/huile dans l'eau - Google Patents

Emulsions multiples eau/huile dans l'eau Download PDF

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Publication number
WO1996028245A1
WO1996028245A1 PCT/EP1996/000943 EP9600943W WO9628245A1 WO 1996028245 A1 WO1996028245 A1 WO 1996028245A1 EP 9600943 W EP9600943 W EP 9600943W WO 9628245 A1 WO9628245 A1 WO 9628245A1
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Prior art keywords
emulsions
emulsifiers
fatty acid
weight
polyhydroxystearates
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PCT/EP1996/000943
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German (de)
English (en)
Inventor
Achim Ansmann
Rolf Kawa
Helga Gondek
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Henkel Kommanditgesellschaft Auf Aktien
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Publication of WO1996028245A1 publication Critical patent/WO1996028245A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
    • 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
    • C09K23/34—Higher-molecular-weight carboxylic acid 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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/066—Multiple emulsions, e.g. water-in-oil-in-water
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A61K9/113—Multiple emulsions, e.g. oil-in-water-in-oil
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/66—Polyesters containing oxygen in the form of ether groups
    • C08G63/664—Polyesters containing oxygen in the form of ether groups derived from hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
    • C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
    • C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • 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
    • 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
    • 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
    • C09K23/18—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2391/00—Characterised by the use of oils, fats or waxes; Derivatives thereof

Definitions

  • the invention relates to multiple W / O / W emulsions containing polyol polyhydroxystearates and surfactants as emulsifiers, a process for their preparation and the use of mixtures of polyol polyhydroxystearates and surfactants as emulsifiers for the production of multiple W / O / W emulsions.
  • Multiple emulsions are emulsions of emulsions. Depending on the production, a distinction is made between multiple water / oil / water (W / O / W) and oil / water / oil (0 / W / O) emulsions.
  • W / O / W water / oil / water
  • oil / water / oil (0 / W / O) emulsions The most important application of multiple emulsions is to process active ingredients that are otherwise not miscible or ready for assembly in a recipe. Another advantage is that the active ingredients can be released in a controlled manner over a longer period of time. Multiple emulsions are therefore particularly suitable for the production of cosmic tables and pharmaceutical products of particular importance [Cosm.Toil. 105, 65 (1990) and ___ 6 r 97 (1991)].
  • W / 0 / W emulsions are also known from Yakuga u Zasshi 112, 73 (1992), which contain glycerol trifatty acid esters as oil bodies and hydrophilic polymers, such as gelatin, as stabilizing agents.
  • the use of albumin and polyacrylates as stabilizers for the water phase and nonionic surfactants for the oil phase is known from J. Controlled Release _, 279 (1986).
  • Such formulations have proven to be insufficiently stable in storage, in particular in the case of temperature fluctuations.
  • EP-AI 0174377 (Meji Milk Products) is also the use of polyglycerol polyricinoleates as emulsifiers for the production of multiple emulsions is known.
  • these emulsions have also proven to be insufficiently stable, particularly in the case of temperature fluctuations.
  • the object of the invention was therefore to provide in one step stable multiple W / O / W emulsions which are also resistant to temperature fluctuations, but which, from an application point of view, have a lipophilic emulsifier which is at least equivalent to cetyl dimethicone copolyols contain improved skin cosmetic properties. Furthermore, the emulsions should be as free as possible from hydrophilic, co-emulsifiers containing ethylene oxide. Description of the invention
  • the invention relates to multiple W / O / W emulsions which are obtained by containing an oil phase in the presence of an emulsifier mixture
  • polyol polyhydroxystearates in general and polyglycerol polyhydroxy stearates in particular, in combination with ethylene oxide-free surfactants are suitable as effective lipophilic emulsifiers for the one-step preparation of multiple W / O / W emulsions and thus a substitute which is at least equivalent from an application point of view represent copolyols for ethylene oxide-containing cetyl dimethicones; at the same time, the ethylene oxide-free polyol polyhydroxystearates, together with surfactant co-emulsifiers, have significantly better skin cosmetic properties.
  • polyol polyhydroxystearates which are suitable as emulsifiers for the production of multiple W / O / W emulsions in the sense of the invention are known substances which can be obtained by the relevant processes of preparative organic chemistry.
  • polyhydroxystearic acid with a degree of self-condensation in the range from 2 to 20, preferably 2 to 10, esterified with polyols in a manner known per se.
  • the polyol polyhydroxystearates can be derived from polyols which have at least two, preferably 3 to 12 and in particular 3 to 8 hydroxyl groups and 2 to 12 carbon atoms.
  • Typical examples are glycerol, alkylene glycols such as ethylene glycol, diethylene glycol, propylene glycol; Polyglycerin; Methyl compounds, such as in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol; Alkyl glucosides with 1 to 22, preferably 1 to 8 and in particular 1 to 4 carbons in the alkyl radical, such as, for example, methyl and butyl glucoside; Sugar alcohols with 5 to 12 carbon atoms such as, for example, sorbitol or mannitol, sugars with 5 to 12 carbon atoms such as, for example, glucose or sucrose; or sugar in sugar such as glucamine.
  • the emulsifiers used are polyglycerol polyhydroxystearates which are obtained by polyhydroxystearic acid having a degree of self-condensation in the range from 2 to 20, preferably 2 to 10, with a polyglycerol mixture of the composition (GC method)
  • Pentaglycerols 2 to 10 (3 to 8) wt% (Oligoglycerols ad 100 wt .-%) esterified in a conventional manner; The preferred areas are indicated in brackets.
  • the polyol polyhydroxystearates can be prepared in a manner known per se.
  • the polyglycerol polyhydroxystearates the polyglycerol is preferably first produced and then the polyhydroxystearic acid, and finally both are esterified.
  • a polyglycerol of the abovementioned composition can be prepared by self-condensation of glycerol in the presence of suitable catalysts such as, for example, potassium carbonate, silicates according to DE-Al 4029323 (Henkel) or borates according to DE-Al 4117033 (Henkel) at temperatures in the range of 200 to 260 ° C are carried out.
  • suitable catalysts such as, for example, potassium carbonate, silicates according to DE-Al 4029323 (Henkel) or borates according to DE-Al 4117033 (Henkel) at temperatures in the range of 200 to 260 ° C are carried out.
  • the polyhydroxystearic acid is prepared, for example, by alkaline-catalyzed polycondensation of hydroxystearic acid, preferably 12-hydroxystearic acid, which is obtained by curing ricinoleic acid or technical castor oil fatty acid. Linear esterification products having 2 to 10 and in particular 2 to 8 fatty acid units are preferably formed.
  • the following distribution (GPC method) is typically achieved:
  • mixtures of hydroxystearic acid and ricinoleic acid or technical castor oil fatty acid which consists of about 90% by weight of ricinoleic acid, are in a weight ratio of 90:10 to 50:50 and preferably 75:25 to 60: 40 used. In the same way, it is possible to condense the acids individually and then to mix the condensates.
  • polystyrene resin for example the polyglycerol with the polyhydroxystearic acid or the mixtures with polyricinoleic acid
  • a complex mixture of homologous polyesters is formed.
  • the proportions of mono-, di-, tri- and oligoesters in the polyol polyhydroxystearates according to the invention and preferably polyglycerol polyhydroxy stearates depend on the conditions of use of the starting compounds.
  • an emulsifier with particularly advantageous application properties is used, which is obtained by subjecting about 1000 kg of 12-hydroxystearic acid to self-condensation until a product with an acid number in the range from 50 to 55 results and this is then further esterified with about 150 kg of polyglycerol of the composition given above until the acid number has decreased to a value of less than 2.
  • the selection of the surfactant co-emulsifiers is not very critical since only the emulsifier and a second, largely arbitrary surfactant component are required to carry out the one-stage production process.
  • anionic surfactants are alkylbenzene sulfonates, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, ⁇ e methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerin ether sulfates, hydroxy acid ether sulfate sulfates, mono-ether ether sulfate sulfates, mono-ether ether sulfate sulfates, mono-ether ether sulfate sulfates, mono-ether ether sulfate sulfates, mono-ether ether sulfate sulfates, mono-ether ether sulfate sulfates, mono-ether ether sulfate sulfates, mono-ether
  • nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, FettLiterepo- lyglycolester, FettTexreamidpolygylcolether, polyglycol ethers, alkoxylated triglycerides, Partialglyceridester, mixed ethers and mixed formals, alk (en) yl oligoglycosides, fatty acid N-alkyl glucamides Fettaminpolygly-, polyol, Zuckerester, Sorbitan esters and polysorbates. If the nonionic surfactants contain polyglycol ether chains, they can be have conventional, but preferably a narrowed homolog distribution.
  • cationic surfactants are quaternary ammonium compounds and ester quats, in particular quaternized fatty acid trialkanolamine ester salts.
  • amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amido betaines, aminopropionates, amino glycinates, imidazolinium betaines and sulfobetaines.
  • the emulsifier mixture should be free from ethylene oxide building blocks, but also because of the superior performance properties, the use of surfactant co-emulsifiers which are selected from the group consisting of sulfosuccinates and ether carboxylic acids is preferred , Fatty acid isethionates, fatty acid taurides, fatty acid sarcosinates, monoglyceride (ether) sulfates, alkyl oligoglucosides, fatty acid N-alkyl glucamides, betaine surfactants and / or protein fatty acid condensates.
  • the weight ratio between the polyhydroxystearates and the surfactant co-emulsifiers can be 1: 1 to 1:20 and preferably 1:10 to 1:15.
  • oil phase can also contain fats, waxes, stabilizers and superfatting agents.
  • Suitable oil bodies are, for example, Guerbet alcohols based on fatty alcohols having 6 to 18, preferably 8 to 10 lenstoffatomen coal, esters of linear C5-C20 fatty ä ren with li ⁇ -linear C6-C20 -Fetta H ⁇ ° h ° f s l ester of branched C6-C13 carboxylic acids with linear Cs-Cig fatty alcohols, esters of linear Cs-Cig fatty acids with branched alcohols, in particular 2-ethylhexanol, esters of linear and / or branched fatty acids with polyhydric alcohols and / or Guerbet alcohols, triglycerides based on C5-C ⁇ o- Fe-tt acids, vegetable oils, branched primary alcohols, substituted cyclohexanes, Guerbet carbonates and / or dialkyl ethers.
  • Guerbet alcohols based on fatty alcohols having 6 to
  • W / O and O / W emulsifiers such as, for example, polyglycerol fatty acid esters or glycerol fatty acid esters can be considered as further co-emulsifiers.
  • Typical examples of fats are glycerides, waxes which may be used include beeswax, paraffin wax or microwaxes, if appropriate in combination with hydrophilic waxes, for example cetylstearyl alcohol.
  • Metal salts of fatty acids such as magnesium, aluminum and / or zinc stearate can be used as stabilizers.
  • 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 optionally serving at the same time as foam stabilizers.
  • the water phase can also contain polyols such as preferably glycerol and electrolyte salts such as sodium chloride, ammonium chloride or magnesium sulfate.
  • polyols such as preferably glycerol and electrolyte salts such as sodium chloride, ammonium chloride or magnesium sulfate.
  • Other important components can be polymers or thickeners. Typical examples of this are 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, polyvinyl alcohol and polyvinyl pyrrolidone.
  • preservatives such as, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid can also be present. Preparation of the
  • Another object of the invention is a process for the preparation of multiple W / O / W emulsions, in which one contains an oil phase in the presence of an emulsifier mixture
  • the oil phase is preferably homogenized at room temperature together with the emulsifier - that is to say the mixture of polyol polyhydroxystearate and preferably polyglycerol polyhydroxystearate with a surfactant co-emulsifier - and into the likewise homogenized water phase stirred in.
  • the emulsifier mixtures are preferably used in amounts of 1 to 10 and in particular 2 to 4% by weight, based on the multiple W / O / W emulsion.
  • the weight ratio between the oil phase and water phase can be in the range from 50:50 to 10:90 and preferably 20:80 to 30:70.
  • the emulsions can also be prepared by cold, hot, hot-hot / cold or PIT emulsification. This is a purely mechanical process, there is no chemical reaction. Industrial applicability
  • the multiple W / O / W emulsions according to the invention are notable for particular stability, in particular even at fluctuating temperatures.
  • Another object of the invention therefore relates to the use of mixtures of polyol polyhydroxystearates and surfactants in general and polyglycerol polyhydroxystearates and ethylene oxide-free non-ionic, ionic or ampholytic surfactants in particular as emulsifiers for the one-stage preparation of multi-plenary W / O / W emulsions , in which they can be contained in amounts of 0.1 to 10, preferably 0.2 to 4% by weight, based on the multiple emulsions.
  • the multiple W / O / W emulsions in turn can be used to produce cosmetic and pharmaceutical preparations such as creams, ointments and lotions.
  • octyl stearate (Cetiol ( R ) 868), 3.0% by weight almond oil, 2.0% by weight paraffin oil, viscous 2.0% by weight cyclomethicone (Dow Corning 344) 0 , 2 wt .-% polyglyceryl-2 polyhydroxystearates
  • Example 1 was repeated, but a mixture of the oil phase
  • coco-caprylate / caprate (Cetiol ( R ) LC), 2.5% by weight dicapryl ether (Cetiol ( R ) OE), 0.6% by weight polyglyceryl-2 polyhydroxystearate
  • Example 1 was repeated, but a mixture of the oil phase

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Abstract

On obtient des émulsions multiples stables eau/huile dans l'eau en émulsifiant avec une phase aqueuse une phase huileuse en présence d'un mélange émulsifiant qui contient (a) des polyolpolyhydroxystéarates et (b) des agents tensioactifs anioniques, non ioniques, cationiques, amphotères et/ou zwitterioniques.
PCT/EP1996/000943 1995-03-15 1996-03-06 Emulsions multiples eau/huile dans l'eau WO1996028245A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19509301.1 1995-03-15
DE19509301A DE19509301A1 (de) 1995-03-15 1995-03-15 Multiple W/O/W-Emulsionen

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WO1996028245A1 true WO1996028245A1 (fr) 1996-09-19

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0784972A3 (fr) * 1995-12-22 1997-11-19 Henkel Kommanditgesellschaft auf Aktien Emulsions cosmétiques et/ou pharmaceutiques
WO1999004749A2 (fr) * 1997-07-25 1999-02-04 Cognis Deuthscland Gmbh Emulsions eau dans l'huile dans l'eau multiples a forte teneur en polyols

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19533539A1 (de) * 1995-09-11 1997-03-13 Henkel Kgaa O/W-Emulgatoren
DE19612084C2 (de) * 1996-03-27 1999-07-08 Henkel Kgaa Verfahren zur Herstellung multipler W/O/W-Emulsionen
DE19719297A1 (de) * 1997-05-07 1998-11-12 Henkel Kgaa Verfahren zur Herstellung multipler W/O/W-Emulsionen
FR2767064B1 (fr) 1997-08-07 1999-11-12 Centre Nat Rech Scient Procede de liberation d'un principe actif contenu dans une emulsion multiple
DE19810012A1 (de) * 1998-03-09 1999-09-16 Henkel Kgaa Kosmetische und/oder pharmazeutische Zubereitungen
DE19821402A1 (de) * 1998-05-13 1999-11-18 Henkel Kgaa Verfahren zur Herstellung von stabilen Emulsionen
DE19828081C2 (de) * 1998-06-24 2000-08-10 Cognis Deutschland Gmbh W/O-Emulsionsgrundlagen
DE10120927A1 (de) * 2001-04-30 2002-10-31 Stockhausen Chem Fab Gmbh Verwendung von multiplen Emulsionen als Hautschutzprodukte

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB723244A (en) * 1951-04-10 1955-02-02 Unilever Ltd Improvements in or relating to surface-active agents
EP0000424A1 (fr) * 1977-07-12 1979-01-24 Imperial Chemical Industries Plc Copolymères à bloc ester-éther, linéaires ou ramifiés, et leur utilisation comme agents tensioactifs, seuls ou en mélanges avec des agents tensioactifs usuels
JPS585142A (ja) * 1981-07-02 1983-01-12 Riken Vitamin Co Ltd Ｌ−アスコルビン酸またはその塩類を含有せる飼料用乳化油脂組成物およびその製造法
EP0120967A1 (fr) * 1982-10-01 1984-10-10 Meiji Milk Products Company Limited Procede de production de compositions alimentaires d'huile et de graisse a emulsion eau/huile/eau
EP0174377A1 (fr) * 1984-03-26 1986-03-19 Meiji Milk Products Company Limited Emulsion du type multiple eau/huile/eau pour usage cosmetique ou medical
US4626443A (en) * 1984-03-02 1986-12-02 Meiji Milk Products Company Limited Process for preparing dressings comprising W/O/W type multiple emulsions
EP0345075A2 (fr) * 1988-06-03 1989-12-06 Unilever Plc Emulsions
JPH04178316A (ja) * 1990-11-09 1992-06-25 Kao Corp 乳化化粧料
WO1992018227A2 (fr) * 1991-04-13 1992-10-29 Beiersdorf Ag Emulsions multiples stables
WO1995017953A1 (fr) * 1993-12-30 1995-07-06 Fmc Corporation Emulsions eau/huile et eau/huile/eau a phase interne elevee
WO1995034528A1 (fr) * 1994-06-13 1995-12-21 Henkel Kommanditgesellschaft Auf Aktien Polyolpolyhydroxystearates

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB723244A (en) * 1951-04-10 1955-02-02 Unilever Ltd Improvements in or relating to surface-active agents
EP0000424A1 (fr) * 1977-07-12 1979-01-24 Imperial Chemical Industries Plc Copolymères à bloc ester-éther, linéaires ou ramifiés, et leur utilisation comme agents tensioactifs, seuls ou en mélanges avec des agents tensioactifs usuels
JPS585142A (ja) * 1981-07-02 1983-01-12 Riken Vitamin Co Ltd Ｌ−アスコルビン酸またはその塩類を含有せる飼料用乳化油脂組成物およびその製造法
EP0120967A1 (fr) * 1982-10-01 1984-10-10 Meiji Milk Products Company Limited Procede de production de compositions alimentaires d'huile et de graisse a emulsion eau/huile/eau
US4626443A (en) * 1984-03-02 1986-12-02 Meiji Milk Products Company Limited Process for preparing dressings comprising W/O/W type multiple emulsions
EP0174377A1 (fr) * 1984-03-26 1986-03-19 Meiji Milk Products Company Limited Emulsion du type multiple eau/huile/eau pour usage cosmetique ou medical
EP0345075A2 (fr) * 1988-06-03 1989-12-06 Unilever Plc Emulsions
JPH04178316A (ja) * 1990-11-09 1992-06-25 Kao Corp 乳化化粧料
WO1992018227A2 (fr) * 1991-04-13 1992-10-29 Beiersdorf Ag Emulsions multiples stables
WO1995017953A1 (fr) * 1993-12-30 1995-07-06 Fmc Corporation Emulsions eau/huile et eau/huile/eau a phase interne elevee
WO1995034528A1 (fr) * 1994-06-13 1995-12-21 Henkel Kommanditgesellschaft Auf Aktien Polyolpolyhydroxystearates

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 8308, Derwent World Patents Index; AN 83-18280K, XP002007544 *
PATENT ABSTRACTS OF JAPAN vol. 16, no. 485 (C - 0993) *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0784972A3 (fr) * 1995-12-22 1997-11-19 Henkel Kommanditgesellschaft auf Aktien Emulsions cosmétiques et/ou pharmaceutiques
WO1999004749A2 (fr) * 1997-07-25 1999-02-04 Cognis Deuthscland Gmbh Emulsions eau dans l'huile dans l'eau multiples a forte teneur en polyols
WO1999004749A3 (fr) * 1997-07-25 1999-04-15 Henkel Kgaa Emulsions eau dans l'huile dans l'eau multiples a forte teneur en polyols

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