EP2307433A2 - Neuartige zusammensetzung auf basis von alkylpolyosidethern und alkylglycerylethern, ihre verwendung als emulgatoren und kosmetische zusammensetzung damit - Google Patents

Neuartige zusammensetzung auf basis von alkylpolyosidethern und alkylglycerylethern, ihre verwendung als emulgatoren und kosmetische zusammensetzung damit

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Publication number
EP2307433A2
EP2307433A2 EP09766071A EP09766071A EP2307433A2 EP 2307433 A2 EP2307433 A2 EP 2307433A2 EP 09766071 A EP09766071 A EP 09766071A EP 09766071 A EP09766071 A EP 09766071A EP 2307433 A2 EP2307433 A2 EP 2307433A2
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EP
European Patent Office
Prior art keywords
composition
formula
weight
mass
oil
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.)
Withdrawn
Application number
EP09766071A
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English (en)
French (fr)
Inventor
Sébastien KERVERDO
Hervé Rolland
Jérôme GUILBOT
Alain Milius
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.)
Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA
Original Assignee
Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA
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Filing date
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Application filed by Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA filed Critical Societe dExploitation de Produits pour les Industries Chimiques SEPPIC SA
Publication of EP2307433A2 publication Critical patent/EP2307433A2/de
Withdrawn legal-status Critical Current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
    • A61K8/062—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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • 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
    • A61K2800/59—Mixtures
    • A61K2800/592—Mixtures of compounds complementing their respective functions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/14—Preparations for removing make-up
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • 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
    • A61Q19/005—Preparations for sensitive skin
    • 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
    • A61Q19/007—Preparations for dry skin

Definitions

  • the invention relates to the provision of novel nonionic emulsifying compositions that can be used in the preparation of cosmetic and / or pharmaceutical formulations, especially for topical use, in the form of oil-in-water emulsions, stable for storage for a prolonged period under stress of temperature.
  • Emulsifiers derived from sugar have been developed for more than twenty years and their commercial success is well established. These commercial compositions consisting of a mixture of alkyl polyglycosides and fatty alcohols are on the market either in solid form, whether they are flakes or pearls, or in liquid form at room temperature if uses branched or unsaturated fatty alcohols to lead to such mixtures. Such emulsifying compositions are described in the international applications published under the numbers WO 92/06778, WO 95/13863, WO 96/37285 or WO 00/56438, or in the French patent application published under the number FR 2 830 464. .
  • EP 0 550 280 A1 discloses glyceroglycolipidic surfactants of fo ⁇ nule: A I- O-CH 2 -CH (OR I ) -CH 2 -OR (a) in which Al is a saccharide residue, R and R1, which are identical or different, represent a hydrogen atom or a linear or branched, saturated or unsaturated hydrocarbon radical containing from 1 to 24 carbon atoms, it being understood that at least two radicals does not represent a hydrogen atom, as well as their use for preparing cleaning or detergent compositions for hard tissues or surfaces, as well as personal care compositions for cleaning the human body such as solid soaps, compositions facial or body cleansing, hair or body shampoo, toothpaste.
  • This patent application more particularly discloses glyceroglycolipidic surfactants such as those of formula (a) in which Al represents a residue of galactose, glucose, mannose, lactose, galactotrioside or cellotrioside, R and R1 represent different alkyl chains.
  • this patent application does not disclose the use of these surfactants as emulsifiers for preparing oil-in-water emulsions which are storage stable for a prolonged time under temperature stress.
  • Ri-O-CH 2 -CH (OR 2) -CH 2 -O- [G] p in which R represents an alkyl, alkenyl or acyl optionally hydroxyl- functionalized and having from 6 to 22 carbon atoms, R2 is hydrogen or R1, G represents a saccharide radical with 5 to 12 carbon atoms and p represents numbers ranging from 1 to 10 and a process for their preparation which consists in etherifying the glycoses with partial ethers of glycerine in the presence of catalysts alkalines and at temperatures ranging from 100 0 C to 180 0 C.
  • the preparation process includes a step of reaction between glucose and the ether of 2-ethylhexyl glycerine acid catalysis, and a step purification consisting in a distillation of the ether of 2-ethylhexyl glycerine.
  • the inventors have therefore sought to develop new non-ionic emulsifying compositions for preparing cosmetic and / or pharmaceutical oil-in-water emulsions with topical application, which are storage-stable for a prolonged time under temperature stress.
  • the subject of the invention is a composition (C) comprising for 100% of its mass: from 10% by weight to 95% by weight, more particularly from 70% by mass to 95% by weight, one or more glycerol ether alcohols of formula (II):
  • R1 represents a linear or branched, saturated or unsaturated aliphatic radical, optionally substituted with one or more hydroxyl groups, having from 16 to 18 carbon atoms, and
  • linear or branched aliphatic radical saturated or unsaturated, optionally substituted with one or more hydroxyl group, comprising from 16 to 18 carbon atoms, is denoted especially for R 1 in formulas (I) and (II) as defined above :
  • linear aliphatic radicals for example the n-hexadecyl, n-octadecyl radicals;
  • unsaturated linear aliphatic radicals such as the radicals hexadecenyl, octadecenyl, octadecadienyl, octadecatrenyl, octadecateternyl, for example the oleyl, isooloyl or linoleyl unsaturated radicals; saturated or unsaturated, linear or branched aliphatic radicals containing from 16 to 18 carbon atoms substituted with one or two hydroxyl groups, such as the hydroxyl hexadecyl, hydroxy octadecyl or dihydroxy-octadecyl radicals, for example the 3-hydroxy radicals; hexadecyl, 4-hydroxy hexadecyl, 11-hydroxy hexadecyl, 16-hydroxy hexadecyl, 12-hydroxy stearyl or 8,9-dihydroxy stearyl.
  • p is a decimal number which represents the average degree of polymerization of the residue G.
  • (G) p is the polymeric residue of rank p the rest G.
  • the formula (I) represents a mixture of compounds: R I r O-CH 2 -CH (OR 2) -CH 2 -OGH + a 2 R r O-CH 2 - CH (OR 2 ) -CH 2 -O- (G) 2 -H + a 3 R 1 -O-CH 2 -CH (OR 2 ) -CH 2 -O- (G) 3 -H + ...
  • p is between 1.05 and 5, and more particularly between 1.05 and 2.
  • residue of a reducing sugar for G in the definition of the compound of formula (I) is meant a residue of saccharide derivatives which do not have in their glycosidic bonding structures established between an anomeric carbon and the oxygen of a acetal group as defined in the reference work: "Biochemistry”, Daniel Voet / Judith G. Voet, p. 250, John Wyley & Sons, 1990.
  • the oligomeric structure (G) p can be in any form of isomerism, whether it is optical isomerism, geometric isomerism or position isomerism; it can also represent a mixture of isomers.
  • the group R 1 -O-CH 2 -CH (OH) -CH 2 -O- is linked to G by the anomeric carbon of the saccharide residue, so as to form a functional group. acetal.
  • the remainder of the reducing sugar G is more particularly chosen from the group consisting of glucose, dextrose, sucrose, fructose, idose, gulose, galactose, maltose, isomaltose, maltotriose, lactose, cellobiose, mannose, ribose, xylose, arabinose, lyxose, allose, altrose, dextran or tallose.
  • the radical R 1 is chosen from hexadecyl, 2-hexyl decyl, octadecyl, oleyl and 12-hydroxy stearyl radicals. , 2-hexyl dodecyl and 2-octyl decyl.
  • G represents the residue of a reducing sugar chosen from glucose, xylose or arabinose.
  • the subject of the invention is also a process for the preparation of a composition (C) as defined above, comprising a step a) of reaction of a reducing sugar G with a stoichiometric excess of glycerol ether alcohol of formula (II) as defined above.
  • step a) is generally carried out in a reactor, by controlling the stoichiometric ratio between the two reactants, and by mechanical stirring under predetermined conditions of temperature and partial vacuum. , for example at a temperature between 70 0 C and 130 0 C and under a partial vacuum between 300 mbar (3 10 4 Pa) and 20 mbar (2 10 3 Pa).
  • acidic catalytic system are meant strong acids such as sulfuric acid, hydrochloric acid, phosphoric acid, nitric acid, hypophosphorous acid, methanesulfonic acid, para-toluene sulfonic acid, trifluoromethanesulfonic acid, or acidic ion exchange resins.
  • the subject of the invention is also a variant of the process as defined above, comprising a step a1) of reaction of a reducing sugar G with an alcohol of formula (III)
  • Step a1) of the variant of the process as defined above is more particularly carried out at a temperature of between 90 ° C. and 105 ° C., under partial vacuum, and often accompanied by the concomitant elimination of the water formed during the reaction.
  • a temperature of between 90 ° C. and 105 ° C. there is more particularly that as defined for the implementation of the preparation process from which said variant.
  • the process and its variant may be, if necessary or desired, supplemented by neutralization, filtration and bleaching operations.
  • composition (C) as defined above can also be prepared by mixing a glycerol ether alcohol of formula (II) or a mixture of glycerol ether alcohols of formula (II) with a compound of formula (I), or a mixture of compound of formula (I), previously prepared separately according to the method or its variant as described above, which, however, include an additional final step of removing the alcohol glycerol ether or alcohols glycerol ethers in excess by carrying out an operation known to those skilled in the art such as, for example, distillation, distillation under partial vacuum by means of a thin-film evaporator or a film-film evaporator thin-path, molecular distillation or solvent extraction.
  • an operation known to those skilled in the art such as, for example, distillation, distillation under partial vacuum by means of a thin-film evaporator or a film-film evaporator thin-path, molecular distillation or solvent extraction.
  • composition (C) comprising for 100% of its mass: from 90% by weight to 5% by weight of a composition (C1) comprising for 100% of its mass, from 10% to 90% mass of at least one compound of formula (I A ) corresponding to formula (I) in which R 1 represents a radical containing 18 carbon atoms, and from 95% to 5% mass of at least one compound of formula (I B ) corresponding to formula (I), in which R 1 represents a radical containing 16 carbon atoms; and
  • composition (C) as defined above can be prepared by mixing the composition (Ci) as defined above with at least one glycerol ether alcohol of formula (H A ) as defined above and at least a glycerol ether alcohol of formula (II B ) as defined above.
  • composition (Ci) can be prepared by various routes.
  • a first route of preparation of the composition (Ci) consists in mixing, in the desired mass proportions, the compound of formula (I A ) as defined above or a mixture of compounds of formula (I A ), with the compound of formula (I B ), as defined above, or a mixture of compounds of formula (I B ).
  • a second route of preparation of the composition (Ci) consists in implementing a process comprising a step a) of reaction of a reducing sugar G with a mixture (Mi) comprising for 100% of its total mass, from 10% to 90% by weight of at least one glycerol ether alcohol of formula (H A ), corresponding to formula (II) for which the radical R 1 represents an aliphatic radical containing 18 carbon atoms, and from 90% to 10% by mass of at least one glycerol ether alcohol of formula (II B ), corresponding to formula (II) for which the radical R 1 represents an aliphatic radical containing 16 carbon atoms, in the presence of an acidic catalyst system.
  • step a) is generally carried out in a reactor, by controlling the stoichiometric ratio between the two reactants, and by mechanical stirring under conditions of temperature and partial vacuum. predetermined, for example at a temperature between 70 0 C and 130 0 C and under a partial vacuum between 300 mbar (3 10 4 Pa) and 20 mbar (2 10 3 Pa).
  • acidic catalytic system strong acids such as sulfuric acid, hydrochloric acid, phosphoric acid, nitric acid, hypophosphorous acid, methanesulfonic acid, para-toluene sulfonic acid, trifluoromethanesulfonic acid, or acidic ion exchange resins.
  • a third route of preparation of the composition (Ci) consists of a variant of the second preparation route as described above, comprising a step a1) of reaction of a reducing sugar G with an alcohol of formula (III) as defined previously, in the presence of an acidic catalyst system, to form the acetal of formula (IV), followed by a step b) transacetalization of the acetal of formula (IV) obtained in step a1), by adding a mixture (M1) as defined above with vacuum distillation of the alcohol of formula (III) formed "in situ” .
  • Step a1) of this third preparation route as described above is more particularly carried out at a temperature of between 90 ° C. and 105 ° C., under partial vacuum, and often accompanied by the concomitant elimination. water formed during the reaction.
  • the mixture (Ml) in excess is removed by the implementation of an operation known to those skilled in the art such as, for example, distillation, distillation under partial vacuum by means of a thin film film evaporator or a direct path thin film evaporator, molecular distillation or solvent extraction.
  • the second preparation route and its variant can be, if necessary or if desired, supplemented by neutralization, filtration and bleaching operations.
  • the composition (C) as defined above may also be prepared by reacting an excess of mixture (Mi) as defined above with the reducing sugar G according to the second preparation route or its variant, as defined. previously, without removing the glycerol ether alcohols of formulas (II A ) and (II B ) included in the unreacted mixture (Mi).
  • the invention also relates to the use of a composition (C) or a composition (C) as defined above, as an emulsifying agent.
  • the subject of the invention is also a composition for topical use in the form of an oil-in-water emulsion comprising for 100% of its mass:
  • composition (C) from 0.1% by weight to 15% by weight of a composition (C) or a composition (C) as defined above, from 5% by mass to 50% by weight of a fatty phase constituted by one or more oils and / or one or more waxes, and
  • topical use used in the definition of the composition being in the form of an oil-in-water emulsion as described above, means that said composition is implemented by application to the skin, the hair, the scalp or the mucous membranes, whether it be a direct application in the case of a cosmetic, dermocosmetic, dermopharmaceutical or pharmaceutical composition or of an indirect application, for example in the case of a personal care product in the form of a textile or paper towel or sanitary products intended to be in contact with the skin or the mucous membranes.
  • oils minerals such as paraffin oil, liquid petrolatum, isoparaffins or mineral white oils
  • oils of animal origin such as squalene or squalane
  • vegetable oils such as phytosqualane, sweet almond oil, coconut oil, castor oil, jojoba oil, olive oil, rapeseed oil, peanut oil, sunflower oil, wheat germ oil, corn germ oil, soybean oil, cottonseed oil, alfalfa oil, poppy oil , pumpkin oil, evening primrose oil, millet oil, barley oil, rye oil, safflower oil,nadooulier oil, passionflower oil , hazelnut oil, palm oil, shea butter, apricot kernel oil, calophyllum oil, sysymbrium oil, avocado oil, calendula, oils derived from flowers or vegetables; ethoxylated vegetable oils
  • As another fat that can be associated with the fatty phase of the composition in the form of an oil-in-water emulsion object of the present invention include linear or branched saturated or unsaturated fatty alcohols , or saturated or unsaturated fatty acids, linear or branched.
  • cosmetically acceptable medium used in the definition of the composition in the form of an oil-in-water emulsion as described above and object of the present invention, means, according to the directive of the Council of European Economic Community No 76/768 / EEC of 27 July 1976 as amended by Directive 93/35 / EEC of 14 June 1993, any substance or preparation intended to be placed in contact with the various parts of the human body (epidermis , hair and hair system, nails, lips and genitals) or with the teeth and oral mucosa in view, exclusively and mainly, to clean, perfume, modify the appearance and / or correct body odor and / or protect or maintain it in good condition.
  • a cosmetically acceptable medium of these compositions which is the subject of the invention may conventionally contain water, one or more cosmetically acceptable organic solvents, a mixture of water and one or more organic solvents.
  • Cosmetically acceptable solvents may more particularly be chosen from polyhydric alcohols, for example glycerol, diglycerol, oligomers of glycerol, ethylene glycol, propylene glycol, hexylene glycol, diethylene glycol, xylitol and the like. erythritol, sorbitol, or water-soluble alcohols such as ethanol, isopropanol or butanol.
  • the composition for topical use according to the invention being in the form of an oil-in-water emulsion further comprises, for 100% of its mass, from 0.1% by mass to 5% by mass. a thickening and / or gelling polymer.
  • thickening and / or gelling polymers which may be associated with the topical composition in the form of an oil-in-water emulsion as defined above and which is the subject of the present invention
  • polymers polyelectrolytes such as, for example, copolymers of acrylic acid and 2-methyl-[(1-oxo-2-propenyl) amino] 1-propane sulfonic acid (AMPS), copolymers of acrylamide and 2-methyl-[(1-oxo-2-propenyl) amino] 1-propanesulfonic acid, copolymers of 2-methyl-[(1-oxo-2-propenyl) amino] 1 propane sulphonic acid and (2-hydroxyethyl) acrylate, the homopolymer of 2-methyl-[(1-oxo-2-propenyl) amino] 1-propane sulphonic acid, the homopolymer of acrylic acid, copolymers of acryloyl ethyl trimethyl ammoni
  • SIMULGEL TM EG Such polymers are marketed under the names SIMULGEL TM EG, SEPIGEL TM 305 and SIMULGEL TM NS respectively.
  • composition for topical use according to the invention being in the form of a water-in-oil emulsion further comprises for 100% of its mass from 0.5% by weight to 10% by weight of dihydroxyacetone.
  • Dihydroxyacetone is a product commonly used in cosmetics as a tanning agent and / or artificial browning of the skin; applied on the latter, it makes it possible to obtain a tanning or browning effect of a more or less similar appearance to that which may result from prolonged exposure to the sun or under an ultraviolet lamp.
  • composition for topical use being in the form of an oil-in-water emulsion comprising for 100% of its mass of 0.5% to 10% by weight of dihydroxyacetone and object of the present invention may also be associated with other agents for tanning and / or browning of the skin, among which mention may be made of mono- or polycarbonyl compounds such as, for example, isatin, alloxane, ninhydrin, glyceraldehyde, mesotartaric aldehyde, glutaraldehyde, erythrulose.
  • mono- or polycarbonyl compounds such as, for example, isatin, alloxane, ninhydrin, glyceraldehyde, mesotartaric aldehyde, glutaraldehyde, erythrulose.
  • the invention also relates to a cosmetic treatment method for tanning and / or artificially browning the skin, characterized in that it consists in applying thereon an effective amount of the composition as defined above.
  • compositions (C) or a composition (C) as defined above for improving the stability of the dihydroxyacetone contained in a cosmetic composition intended for tanning and / or browning. artificial skin.
  • Topical compositions in the form of an oil-in-water emulsion as defined above and objects of the present invention may be prepared in the following manner:
  • the aqueous phase is heated at a temperature of between 60 ° C. and 85 ° C .;
  • the fatty phase comprising the emulsifying system object of the present invention and the oils and / or waxes is heated to a temperature between 60 0 C and 85 ° C.
  • the two phases are then mixed and emulsified using an emulsifier of the type stator rotor (such as a SILVERSON or ULTRA TURRAX laboratory foam concentrate).
  • an emulsifier of the type stator rotor such as a SILVERSON or ULTRA TURRAX laboratory foam concentrate.
  • the emulsion is cooled with moderate stirring at a speed of between 50 rpm and 200 rpm.
  • the thickening and / or gelling polymer or the thickening and / or gelling polymer mixtures are introduced into the aqueous phase, or into the oily phase or directly into the emulsion according to the suppliers' recommendations. If the components of each phase or of all phases are liquid at ambient temperature, the preparation of said phase or of the emulsion can be carried out without heating.
  • compositions for topical use in the form of an oil-in-water emulsion as defined above and objects of the present invention may be in the form of creams, milks, cream gels, fluid lotions, vaporizable fluid lotions.
  • compositions for topical use which are in the form of oil-in-water emulsions as defined above, also comprise excipients and or active principles usually used in the field of topical formulations, in particular cosmetic formulations.
  • dermocosmetics pharmaceuticals or dermopharmaceuticals, such as thickening and / or gelling surfactants, stabilizers, film-forming compounds, hydrotropic agents, plasticizing agents, emulsifying and co-emulsifying agents, opacifying agents, pearlescent agents, superfatting agents, sequestering agents, chelating agents, antioxidants, perfumes, preservatives, conditioners, bleaching agents for hair and skin discoloration
  • active principles intended to provide a treating action with respect to skin or hair sunscreens, mineral fillers or pigments, particles providing a visual effect or intended for the encapsulation of active ingredients, exfoliating particles, texture agents, optical brighteners, repellents for insects.
  • emulsifiers possibly present in the compositions for topical use in the form of oil-in-water emulsions which are the subject of the present invention
  • fatty esters of optionally alkoxylated alkylpolyglycosides, and especially ethoxylated methylpolyglucoside esters such as PEG 120 methyl glucose trioleate and PEG 120 methyl glucose dioleate respectively marketed under the names GLUCAMATE TM LT and GLUMATE TM DOE120
  • alkoxylated fatty esters such as PEG 150 pentaerythrityl tetrastearate marketed under the name CROTHIX TM DS53, PEG 55 propylene glycol oleate sold under the name ANTIL TM 141
  • fatty chain polyalkylene glycol carbamates such as PPG 14 laureth isophoryl dicarbamate marketed under the name ELFACOS TM T211, PPG 14 palmeth 60 hex
  • opacifying agents e and / or pearlescent agents optionally present in compositions for topical use in the form of oil-in-water emulsions which are the subject of the present invention, mention may be made of palmitates or stearates or hydroxystearates of sodium or of magnesium, monostearates or distearates ethylene or polyethylene glycol, fatty alcohols, homopolymers and copolymers of styrene such as the styrene acrylate copolymer sold under the name MONTOPOL TM OP1 by the company SEPPIC.
  • Examples of active principle that may be present in the compositions for topical use, in the form of oil-in-water emulsions that are the subject of the present invention include: compounds having a lightening or depigmenting action, such as, for example, arbutin, kojic acid, hydroquinone, ellagic acid, vitamin C or vitamin C derivatives such as magnesium ascorbyl phosphate, polyphenol extracts, grape extracts, pine extracts, wine extracts, olive extracts, marc extracts, apple juice extracts; amino acid derivatives such as, for example, undecelenoyl phenylalanine sold under the name SEPIWHITE MSH, peptides; total hydrolysts of protein; partial hydrolysts of proteins; polyols (such as, for example, glycerin or butylene glycol); urea; pyrrolidonecarboxylic acid or derivatives thereof; glycyrrhetinic acid; alpha-bisabolol; sugars or
  • sunscreens optionally present in the composition for topical use in the form of an oil-in-water emulsion which is the subject of the present invention, mention may be made of all those appearing in cosmetic directive 76/768 / EEC as amended. The following examples illustrate the invention without limiting it.
  • Example 1 Preparation of a composition (X) consisting of n-hexadecyl ether of glycerol and n-hexadecyl ether of glycerol polyglucosides.
  • a composition (X) consisting of n-hexadecyl ether of glycerol and n-hexadecyl ether of glycerol polyglucosides.
  • n-hexadecyl glycerol ether chimyl or alcohol
  • a coolant circulates, and provided with an effective stirring
  • 31.5 g of anhydrous glucose are then gradually added to the reaction medium to allow its homogeneous dispersion.
  • the homogeneous mixture is maintained at a temperature of 80 ° C.
  • reaction medium is placed under a partial vacuum of 90 mbar to 45 mbar, and maintained at a temperature of 100 0 C- 105 0 C for a period of 5 hours with evacuation of the water formed by means of a distillation assembly .
  • the reaction medium is then cooled to 85 ° C.-90 ° C. and neutralized by adding 0.3 g of 40% sodium hydroxide to bring the pH of a 5% solution of this mixture to a value of about 6%. 5.
  • Example 2 Preparation of a composition Y consisting of n-octadecyl ether of glycerol and n-octadecyl ether of glycerol polyglucosides.
  • n-octadecyl glycerol ether bathyl or alcohol
  • a coolant circulates, and provided with an effective stirring, at a temperature of 80 0 C for allow the total melting n-octadecyl ether of glycerol.
  • 31.5 g of anhydrous glucose are then gradually added to the reaction medium to allow its homogeneous dispersion.
  • the homogeneous mixture is maintained at a temperature of 80 ° C. for 30 minutes, then 0.3 g of 98% sulfuric acid and 0.25 g of 50% hypophosphorous acid are introduced into the homogeneous dispersion prepared beforehand.
  • the reaction medium is placed under a partial vacuum of 90 mbar to 45 mbar, and maintained at a temperature of 100 0 C- 105 0 C for a period of 5 hours with evacuation of the water formed by means of a distillation assembly .
  • the reaction medium is then cooled to 85 ° C.-90 ° C. and neutralized by addition of 0.3 g of 30% sodium hydroxide to bring the pH of a 5% solution of this mixture to a value of about 6%. 5.
  • Example 3 Preparation of a composition Z consisting of n-hexadecyl ether of glycerol, n-octadecyl ether of glycerol, n-hexadecyl ether of glycerol polyglucosides and n-octadecyl ether of glycerol polyglucosides.
  • 149.7 g of glycerol n-hexadecyl ether and 161.4 g of glycerol n-octadecyl ether are introduced into a double-jacketed glass reactor, in which a heat-transfer fluid circulates, and provided with efficient stirring.
  • compositions (X), (Y) and (Z) are prepared using, in the emulsifying system, compositions (X), (Y) and (Z) according to US Pat. invention compared to a prior art emulsifier consisting of cetearyl polyglucosides and cetearyl alcohol, marketed under the name Montanov TM 68 by the company SEPPIC.
  • Emulsions E 1 to E 23 contained in Examples 4 to 7 are prepared according to the following common procedure:
  • the fatty phase is introduced into a reactor and brought to a temperature of 80 ° C.
  • the emulsifying system is then introduced into the fatty phase at a temperature of 80 ° C., and the mixture obtained is homogenized for 30 minutes via an agitator provided with an anchor-type mobile at a speed of 80 rpm.
  • the water is then added at a temperature of 80 ° C., and the resulting mixture is then sheared by means of a rotor-stator emulsifier, sold by the company Silverson, for a period of 4 minutes at a rate of 4000 rpm.
  • the preserving agent is then introduced into the emulsified mixture thus obtained, which is then cooled to room temperature and stirred for an additional 10 minutes using an agitator equipped with an anchor-type mobile at a speed of 10 minutes. 80 rpm.
  • the emulsion comprises a thickening and / or gelling polymer in its composition, it is introduced onto the mixture consisting of the fatty phase and the emulsifier system at a temperature of 80 ° C., before the step of adding the 'water.
  • the emulsions prepared are then stored in an isolated climatic chamber and regulated at a temperature of 20 ° C. for 7 days.
  • the appearance of the prepared emulsion is observed and the viscosity of the emulsion is measured.
  • the viscosity of the water-in-oil emulsion measured after 7 days at 20 ° C. is characteristic of a system in thermodynamic equilibrium, thus constituting a point of reference for the destabilization that may cause storage for a longer time and at a higher temperature.
  • the emulsions are then stored in an isolated climatic chamber and regulated at a temperature of 45 ° C. for a period of 3 months. After a period of one month, the emulsions are removed from the climatic chamber to measure its viscosity and then reintroduced into the same climatic chamber to continue storage at a temperature of 45 ° C.
  • Example 4 Demonstration of the improvement of the stability of oil-in-water emulsions, comprising an apolar oil phase in the absence of thickening and / or gelling polymers.
  • Table 2 Composition and characterization of emulsions E1 to E3.
  • Table 2 (continued): Composition and characterization of emulsions E4 to E6.
  • the oil-in-water emulsions comprising an apolar phase, prepared with the composition (Y) according to the invention are stable after storage for a period of 3 months at a temperature of 45 ° C.
  • the use of the composition (Y) according to the invention makes it possible to stabilize the value of the viscosity of the oil-in-water emulsion prepared with an apolar phase after storage at 45 ° C. for a period of 3 months: thus, the viscosity of the emulsion El, comprising the Cetyl polyglucoside / cetearyl alcohol mixture as an emulsifying agent decreases by 66.9% after one month storage at 45 ° C. while the viscosity of the emulsion E 2 increases.
  • Example 5 Demonstration of the improvement of the stability of oil-in-water emulsions, comprising a polar oil phase in the absence of thickening and / or gelling polymers.
  • oil-in-water emulsions comprising a polar phase, prepared with the compositions (X), (Y) and (Z) according to the invention, are stable and homogeneous after storage of a duration of 3 at a temperature of 45 ° C.
  • comparative emulsions comprising, as emulsifier, the cetearyl polyglucoside / cetearyl alcohol mixture, defrost before one month of storage at a temperature of 45 ° C.
  • the viscosity of the emulsion El 5 decreases by 38% after one month of storage at 45 ° C. whereas during the same period and under the same storage conditions, the viscosity of the emulsion El 7 comprising the composition (Y) according to the invention increases.
  • a mass content of 5% of the composition (Y) according to the invention makes it possible to stabilize and increase the viscosity of the emulsion after one month of storage at 45 ° C.
  • the viscosity of the comparative emulsion (emulsion E21) comprising the same mass content of 5% of the emulsifying agent consisting of the cetearyl polyglucoside / cetearyl alcohol mixture, decreases by 34.5% after one month of storage at a temperature of 45 ° C.
  • Example 8 Demonstration of the improvement of the color stability of self-tanning oil-in-water emulsions.
  • Dihydroxyacetone has the disadvantage of degrading over time, causing storage problems over time which generally result in undesired yellowing of compositions containing it.
  • oil-in-water emulsions are prepared by using in the emulsifying system the compositions (Y) and (Z) according to the invention in comparison with an emulsifying agent of the invention.
  • state of the art consisting of cetearyl polyglucosides and cetearyl alcohol, marketed under the name Montanov TM 68 by the company SEPPIC.
  • Emulsions E24 to E26 are prepared according to the following common procedure:
  • the components of the fatty phase are melted separately at a temperature of 80 ° C., then introduced into a reactor and homogenized at a temperature of 80 ° C. for 15 minutes using a stirrer equipped with a mobile-type device "Anchor" at a stirring speed of 80 rpm;
  • the aqueous phase is prepared in parallel in a beaker by mixing, at a temperature of 80 ° C., water, glycerol and propylene glycol;
  • the thickening polymer is added to the previously prepared fatty phase, and the resulting mixture is then homogenized at a temperature of 80 ° C. for 15 minutes; the aqueous phase is added to the mixture comprising the fatty phase and the thickening polymer;
  • the resulting mixture is then sheared using a "rotor-stator” emulsifier, marketed by the company SILVERSON, for a period of 4 minutes at a speed of 4000 rpm, at a temperature of 80 ° C. C. -
  • the emulsion obtained is then stirred for 30 minutes using an agitator equipped with an “anchor” type mobile at a stirring speed of 100 rpm, then allowed to cool;
  • the emulsion obtained is kept stirring for 15 minutes with the aid of an agitator equipped with an "anchor" type mobile at a stirring speed of 100 revolutions / minute.
  • compositions of each emulsion E24 to E26 are shown in Table No. 6 below, as well as the characterization of their appearance and the evolution of their color ( ⁇ E) after storage for 3 months at 45 ° C.
  • the parameters L *, a * and b *, constituting the color of each emulsion, are measured with a chromameter Minolta CR200 type marketed by MINOLTA, so as to measure the corresponding ⁇ E value.
  • Example 8 show that the oil-in-water emulsions comprising dihydroxyacetone, prepared with the compositions (Y) and (Z) according to the invention, give rise to a reduced evolution of the coloration after storage of a duration of 3 months at a temperature of 45 ° C relative to the comparative emulsion comprising as emulsifier the cetearyl polyglucoside / cetearyl alcohol mixture.
  • Composition Y 2%
  • Carrageenan ⁇ 0.10%
  • Titanium dioxide 7.0%
  • Tetrasodium EDTA 0.05%
  • Example 12 Body Milk Composition (Y): 3.5%
  • Example 14 moisturizing cream for oily skin
  • Example 15 AHA cream for sensitive skin N-lauryl amino acid mixture: 0.1% to 5%
  • Aspartate magnesium and potassium 0.002% to 0.5%
  • Example 17 Solar milk Composition (Y): 3.5% LANOL TM 37T: 10.0% PARSOL TM MCX: 5.0% EUSOLEX TM 4360: 2.0% Water: q.s. 100% SEPIPLUS TM 400: 1.8% Preservative: 0.2% Perfume: 0.4%
  • Example 18 Cream with AHA Composition (Y): 5.0%
  • Titanium oxide 8%
  • Vitamin A Palmitate 0.2% Vitamin E Acetate: 1%
  • Example 29 Self-bronzing cream with ⁇ -hydroxy acids
  • Aspartate magnesium and potassium 0.002% to 0.5%
  • MONTANOV TM 68 cetearyl glucoside / cetearyl alcohol
  • CAPIGEL TM 98 is a liquid thickener based on acrylate copolymer sold by the company SEPPIC.
  • LANOL TM 99 is isononyl isononanoate sold by the company SEPPIC.
  • the MICROPEARL TM M 100 is an ultra-fine powder with a very soft touch and mattifying action marketed by MATSUMO.
  • SEPICIDE TM CI imidazolidine urea
  • imidazolidine urea is a preservative marketed by the company
  • PEMULEN TM TRl is an acrylic polymer marketed by GOODRICH.
  • SIMULSOL TM 165 is self-emulsifiable glycerol stearate marketed by the company SEPPIC.
  • SEPICIDE TM HB which is a mixture of phenoxyethanol, methylparaben, ethylparaben, propylparaben and butylparaben, is a preservative marketed by the company SEPPIC.
  • PARSOL TM MCX is octyl para-methoxy cinnamate; marketed by the company
  • LANOL TM 37T is glycerol triheptanoate, marketed by the company SEPPIC.
  • SOLAGUM TM L is a carrageenan marketed by the company SEPPIC.
  • EUSOLEX TM 4360 is a solar filter marketed by MERCK.
  • DEEP ALINE TM PVB is an acylated wheat protein hydrolyzate marketed by the company
  • PROTEOL TM APL is a foaming surfactant marketed by the company SEPPIC
  • MICROPEARL TM M 305 is a silky, water-dispersible powder based on a cross-linked methyl methacrylate copolymer.
  • SIMULGEL TM EG Self-invertible inverse copolymer latex such as those described in the international publication WO 99/36445 (INCI name: Sodium acrylate / sodium acryloyldimethyl taurate copolymer and Isohexadecane and Polysorbate 80) sold by the company SEPPIC.
  • SEPIPLUS TM 400 Self-invertible inverse latex of copolymers such as those described in the international publication WO 2005/040230 (INCI name: Polyacrylate-13 &
  • Polysorbate 60 sold by the company SEPPIC.
  • SIMULGEL TM INS 100 Self-Inverting Reverse Latex of Thickening Copolymers
  • SIMULGEL TM 600 self-invertible inverse latex of thickening copolymers (INCI name: acrylamide / Sodium acryloyldimethyl taurate copolymer and Isohexadecane and Polysorbate 80) sold by the company SEPPIC.
  • SEPIGEL TM 305 self-invertible inverse latex of thickening copolymers (INCI name: polyacrylamide and C13-C14 isoparaffin and Laureth-7) sold by the company SEPPIC.
  • PRIMOL TM 352 is a mineral oil marketed by the company EXXON.
  • PECOSIL TM DCT is sodium Dimethicone PEG-7 Acetyl Methyltaurate marketed by the company PHOENIX.
  • PECOSIL TM PS 100 is Dimethicone PEG-7 marketed by the company PHOENIX.
  • DC 200/350 is a cyclomethicone marketed by Dow Corning.

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EP09766071A 2008-06-20 2009-06-15 Neuartige zusammensetzung auf basis von alkylpolyosidethern und alkylglycerylethern, ihre verwendung als emulgatoren und kosmetische zusammensetzung damit Withdrawn EP2307433A2 (de)

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FR0854086A FR2932801B1 (fr) 2008-06-20 2008-06-20 Nouveaux ethers d'alkyl polyosides, leur utilisation comme emulsionnant et compositions cosmetiques les renfermant apg sur alkyl glyceryl ethers.
PCT/FR2009/051127 WO2009153509A2 (fr) 2008-06-20 2009-06-15 Nouvelles compositions a base d'ethers d'alkyl polyosides et d'alkyl glyceryl ethers, leur utilisation comme emulsionnant et compositions cosmetiques les renfermant

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CN103816072A (zh) * 2014-01-24 2014-05-28 娇时化妆品（杭州）有限公司 一种植物精粹窈窕纤体霜
FR3073853B1 (fr) * 2017-11-21 2019-11-01 Societe D'exploitation De Produits Pour Les Industries Chimiques Seppic Latex inverse auto-inversible, comprenant comme agent inverseur des alkylpolyglycosides et son utilisation comme agent epaississant d'une formulation detergente ou nettoyante a usage industriel ou menager
FR3074687B1 (fr) * 2017-12-12 2020-07-17 Societe D'exploitation De Produits Pour Les Industries Chimiques Seppic Nouveaux alkyl polyrhamnosides, procede pour leur preparation et composition cosmetiques et/ou pharmaceutiques en comprenant

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FR2668080B1 (fr) * 1990-10-17 1993-08-13 Seppic Sa Compositions auto-emulsionnables a base d'alcools gras, leur procede de preparation et leur utilisation pour la realisation d'emulsions.
CA2086228C (en) * 1991-12-31 1998-09-22 Robert W. Humphreys Glycolipid surfactants and compositions containing them
FR2706299B1 (fr) * 1993-06-10 1995-09-01 Oreal Emulsion cosmétique ou dermatologique huile-dans-eau contenant une composition auto-émulsionnable à base d'un alcool gras et d'un alkylpolyoside et un co-émulsionnant.
FR2712595B1 (fr) * 1993-11-19 1995-12-22 Seppic Sa Un concentré comportant des alkylglycosides et ses utilisations.
FR2734496B1 (fr) * 1995-05-24 1997-07-04 Seppic Sa Composition emulsionnante a base d'alkylpolyglycosides, et ses utilisations
DE19728900A1 (de) * 1997-07-07 1999-01-14 Henkel Kgaa Hydrophile Glykoside
FR2789330B1 (fr) * 1999-02-10 2001-03-09 Agro Ind Rech S Et Dev Ard Emulsion stable, son procede de preparation et agent a cet effet,qui comprend un alcool gras et des polyglycosides
FR2790977B1 (fr) * 1999-03-19 2003-09-12 Seppic Sa Nouvelles emulsions eau-dans-huile stables contenant un emulsionnant a base d'oleyl- et/ou d'isostearyl-glycoside

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FR2932801A1 (fr) 2009-12-25
WO2009153509A2 (fr) 2009-12-23
CN102066395A (zh) 2011-05-18

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