WO1993024106A1 - Composition comprising a proanthocyanidin oligomer encapsulated in a liposome - Google Patents
Composition comprising a proanthocyanidin oligomer encapsulated in a liposome Download PDFInfo
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- WO1993024106A1 WO1993024106A1 PCT/FR1992/000475 FR9200475W WO9324106A1 WO 1993024106 A1 WO1993024106 A1 WO 1993024106A1 FR 9200475 W FR9200475 W FR 9200475W WO 9324106 A1 WO9324106 A1 WO 9324106A1
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- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 239000008169 grapeseed oil Substances 0.000 description 1
- 230000003859 lipid peroxidation Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229940042880 natural phospholipid Drugs 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- HEGSGKPQLMEBJL-RKQHYHRCSA-N octyl beta-D-glucopyranoside Chemical compound CCCCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HEGSGKPQLMEBJL-RKQHYHRCSA-N 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 229950011087 perflunafene Drugs 0.000 description 1
- UWEYRJFJVCLAGH-UHFFFAOYSA-N perfluorodecalin Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)C2(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C21F UWEYRJFJVCLAGH-UHFFFAOYSA-N 0.000 description 1
- 208000028169 periodontal disease Diseases 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 229940061311 procyanidolic oligomer Drugs 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940080236 sodium cetyl sulfate Drugs 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K8/14—Liposomes; Vesicles
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
-
- 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
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9783—Angiosperms [Magnoliophyta]
- A61K8/9789—Magnoliopsida [dicotyledons]
-
- 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
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9783—Angiosperms [Magnoliophyta]
- A61K8/9794—Liliopsida [monocotyledons]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/42—Colour properties
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
-
- 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
Definitions
- composition comprising a proanthocyanldlnlque ogl lomere encapsulated in an iposome
- the present invention relates to a cosmetic or pharmaceutical composition
- a cosmetic or pharmaceutical composition comprising a proanthocyanidin oligomer intended for the protection of the mucous membranes, of the human epidermis and of the hair against the free radicals involved in oxidation phenomena; it also relates to a corresponding protection process.
- procyanidolic oligomers are agents with strong anti-free radical activity, useful for medicinal and cosmetic uses.
- patent EP-A-301,975 describes compositions intended for the treatment of periodontal diseases containing a procyanidolic oligomer.
- This antioxidant activity has also been described for proanthocyanidin substituted derivatives in US Pat. No. 4,797,421, which also proposes the use of said derivatives in cosmetics.
- the oligomers which are di-, tri- or tetra-mothers, are preferred.
- antioxidant oligomers stems in particular from the fact that they are extracted from various plants and are not toxic unlike synthetic antioxidants, such as butyl hydroxy toluene or butyl hydroxyanisole.
- synthetic antioxidants such as butyl hydroxy toluene or butyl hydroxyanisole.
- the corresponding extraction processes have in particular have been described in FR-A-2,643,073 or indicated by reference in US-A-4,797,421 mentioned above.
- compositions containing a procyanidolic or proanthocyanidin oligomer has the drawback of staining living tissues, teeth or clothing in contact with the skin treated with such compositions.
- amphiphilic lipids have the property of forming mesomorphic phases, the state of organization of which is intermediate between the crystalline state and the liquid state and that, among them, some are capable of swelling. in the presence of an aqueous solution to form a lamellar phase and then, after stirring, to form vesicles or spherules dispersed in an aqueous phase.
- These vesicles are formed by substantially concentric sheets made up of one or more multimolecular layers, preferably bimolecular, encapsulating an aqueous phase and constituting a lipid membrane.
- the above-mentioned vesicles can be prepared by many methods.
- a first method which is for example 0 described by BANGHAM and others. (J. Mol. Bio., 13, 1965, pages 238 to 262)
- the lipid phase is dissolved in a volatile solvent
- a thin film of lipid phase is formed on the walls of a bottle by evaporation of the solvent
- we introduce the phase to be encapsulated on the lipid film and the mixture is stirred mechanically until the dispersion of vesicles of the desired size is obtained; an aqueous dispersion of vesicles encapsulating an aqueous phase is thus obtained, the encapsulated aqueous phase and the aqueous dispersion phase being identical.
- the lipid phase is prepared by mixing the amphiphilic lipid (s) and any additives, at a temperature where the mixture is melted , if the mixture is not liquid at room temperature; a lamellar phase is formed by introducing the aqueous phase to be encapsulated; then the lamellar phase is dispersed in the form of vesicles, using an ultra-disperser, a homogenizer or ultrasound, in an aqueous dispersion phase; in a variant of this process, the formation of the lamellar phase does not constitute a separate stage of the process.
- the vesicles obtained by these two processes are generally of the "multi-sheet" type.
- a process can be used, which consists in dissolving the lipid mixture with octyl glucoside and in forming the vesicles according to the teaching of FR-A-2,543,018.
- This list of processes is in no way limiting and the invention defined below is applicable whatever the process of manufacturing the vesicles.
- the formulation of proanthocyanidin oligomers in vesicles of amphiphilic lipids makes it possible to reduce the staining of living tissues, teeth or clothing in contact with the treated skin, while maintaining at least at the same level. anti-free radical activity of the active agent.
- better stability of the active agent is observed when it is included in amphiphilic lipid vesicles, which allows better preservation over time of the compositions with respect to lipid peroxidation as well as better preservation over time of the anti-free radical properties of the proanthocyanidin oligomers encapsulated in the vesicles.
- the subject of the present invention is therefore a cosmetic or pharmaceutical composition for protecting the mucous membranes, the skin or the hair of a human subject against free radicals involved in oxidation phenomena, said composition containing at least one proanthocyanidin oligomer formed from at least one dimer, trimer or tetramer having an elementary unit corresponding to the formula:
- composition being characterized in that it is formed from an aqueous dispersion of vesicles made up of a membrane of lipid phase, which encapsulates an aqueous phase and comprises at least one ionic amphiphilic lipid and / or at least one nonionic amphiphilic lipid, the encapsulated aqueous phase containing at least partially the proanthocyanidin oligomer (s) .
- the proanthocyanidin oligomers obtained from the elementary units of formula (I) are compounds having excellent solubility in water.
- the major part of the oligomers is present in the encapsulated aqueous phase, the optional residue being in the aqueous dispersion phase.
- the oligomers the elementary unit of formula (I) of which corresponds to the case where R and R4 represent hydrogen and R2 and R3 represent a hydroxyl group.
- the oligomers used in the compositions according to the invention can be extracted from at least one plant chosen from the group formed by: - red vine leaves (product sold under the name sales of "OPC PRECIPITES VIGNE ROUGE” by the company "ADF
- oligomers for the compositions according to the invention, it is also possible to use the products defined in European patent application 348 781.
- all the ionic and / or non-ionic amphiphilic lipids capable of forming vesicles stable, alone or in admixture with additives having the function of reducing the permeability of the membranes of the vesicles and of improving their stability, can be used to constitute the lipid membranes of the vesicles of the compositions according to the invention.
- the lipid phase constituting the membranes of the vesicles of the composition according to the invention can therefore comprise, in a known manner, at least one lipid chosen from the group formed by:
- nonionic lipids defined below: (1) glycerol derivatives, linear or branched, of formula
- R Q represents: (a) an aliphatic chain, linear or branched saturated or unsaturated, containing from 12 to 30 carbon atoms; or hydrocarbon radicals of lanolin alcohols; or the remains of long-chain alpha-diols; (b) a residue R 2 lCO, where R21 is a C11-C29 aliphatic radical, linear or branched;
- R17 can take the meaning (a) or (b) given for
- R23 takes the meaning (a) given for R Q -
- polyglycerol ethers linear or branched, comprising two fatty chains
- polyglycerol ethers linear or branched, comprising two fatty chains
- fatty chain diols (3) fatty chain diols
- fatty alcohols oxyethylenated or not sterols such as for example cholesterol and phytosterols oxyethylenated or not;
- R 2 4- CH0H-CH-C0A ttZH)
- R24 denotes an al yl or C7-C21 alkenyl radical
- C7-C31 COA designates a group chosen from the following two groups.
- B is an alkyl radical derived from primary or secondary, mono- or polyhydroxylated amines; and. R denotes a hydrogen atom or a methyl, ethyl or hydroxyethyl radical; and. a residue -COOZ, where Z represents the remainder of a C3-C7 polyol.
- anionic amphiphilic lipids such as: • natural phospholipids, in particular egg or soy lecithin, or sphingomyelin, phospholipids modified by chemical or enzymatic means, in particular hydrogenated lecithin, and synthetic phospholipids, including dipalmitoylphosphatidylcholine; • anionic compounds, such as those described in French Patent No. 2,588,256 and represented by the formula:
- Rg represents a C7-C21 alkyl or alkenyl radical.
- R9 represents a C7-C31 saturated or unsaturated hydrocarbon radical, and
- M represents H, Na, K, NH4 or a substituted ammonium ion derived from an amine;
- anionic compounds such as the phosphoric esters of fatty alcohols, for example diketylphosphate and dimyristylphosphate in the form of acids or alkaline salts; heptylnonylbenzene sulfonic acid; acid cholesterol sulfate and its alkali salts and acid cholesterol phosphate and its alkali salts; lysolecithins; alkyl sulfates, for example sodium cetyl sulfate; gangliosides;
- cationic amphiphilic lipids such as:
- Non-lipid additives such as certain polymers such as, for example, polypeptides and proteins, can be added to the lipid phase constituting the membrane of the vesicles.
- the amphiphilic lipids used together represent, preferably from 1 to
- the aqueous dispersion of the composition according to the invention comprises an aqueous dispersion phase, which may consist of water, or a mixture of water and at least one solvent miscible with water, such as C1-C7 alcohols and C1-C5 alkyl polyols.
- the aqueous dispersion phase can also contain compounds in solution, such as sugars, organic or mineral salts or polymers.
- concentration in total lipid phase in the composition is between 0.01% and 50% by weight, preferably between 1% and 20% by weight relative to the total weight of the composition.
- the dispersed vesicles have dimensions between 20 and 3000 nm, preferably between 20 and 500 nm.
- the total concentration of proanthocyanidin oligomer (s) in the composition is between 0.01 and 2% by weight relative to the total weight of the composition.
- the aqueous dispersion phase can also contain a dispersion of droplets of a liquid immiscible with water, which the vesicles stabilize. Consequently, in the presence of vesicles of ionic amphiphilic lipids and / or nonionic amphiphilic lipids, it is not necessary to introduce a usual emulsifier such as glycerol monostearate.
- the droplets of such a dispersion generally have sizes between 100 and 10,000 nm.
- the water-immiscible liquid which can be present in the form of a dispersion of droplets in the aqueous dispersion phase, can in particular be:
- an animal or vegetable oil formed by fatty acid and polyol esters in particular liquid triglycerides, for example chosen from the group formed by sunflower, corn, soya, squash, grapeseed oils , jojoba, sesame, hazelnut, fish oils, glycerol tricaprocaprylate, or a vegetable or animal oil of formula R19COOR2O :.
- Ri 9 represents the remainder of a higher fatty acid containing from 7 to 19 carbon atoms and R20 represents a branched hydrocarbon chain containing from 3 to 20 carbon atoms, for example Purcellin oil;
- hydrocarbons such as hexadecane and paraffin oil
- - halogenated carbides in particular fluorocarbons such as fluoroamines, for example perfluorotributy lamin, fluorinated hydrocarbons, for example perfluorodecahydronaphthalene, fluoroesters and fluoroethers;
- silicones for example polysiloxanes, polydimethylsiloxanes and fluorosilicones
- composition according to the invention can be in the form of a lotion, thickened lotion, gel, cream, serum, milk, ointment, solid stick, foam or spray.
- composition according to the invention may, in addition, contain at least one cosmetic adjuvant chosen from the group formed by fatty substances, organic solvents, silicones, thickeners, softeners, sun filters UV-A, UV-B or broadband, self-tanning agents, anti-foaming agents, moisturizing agents, perfumes, preservatives, bactericides, anti-dandruff agents, anti-hair loss agents, antioxidant agents, antiseborrhoeic agents, healing agents, antimicrobial agents, surfactants, fillers, sequestrants, anionic, cationic, nonionic, amphoteric polymers or their mixtures, propellants, basifying or acidifying agents, dyes, pearlescent agents and metal oxide pigments.
- at least one cosmetic adjuvant chosen from the group formed by fatty substances, organic solvents, silicones, thickeners, softeners, sun filters UV-A, UV-B or broadband, self-tanning agents, anti-foaming agents, moisturizing agents, perfumes, preservatives
- composition according to the invention When used for the protection of the human epidermis against free radicals, it can effectively be in the form of a cream, a milk, an ointment, a gel, a solid stick or aerosol foam.
- composition according to the invention when used for protecting the hair, it may be in the form of shampoo, lotion, gel, rinse-out composition, to be applied before or after shampooing, before or after coloring or bleaching, before , during or after permanent or straightening, lotion or gel styling or treating, lotion or gel for brushing or styling, hairspray, composition for permanent or straightening, coloring or bleaching of hair.
- composition according to the invention when used as a makeup product for the eyelashes, the eyebrows or the skin, such as an epidermis treatment cream, foundation, lipstick stick, eyeshadow, blush , liner also called “eye liner” or mascara, it can be in pasty or aqueous form.
- compositions for oral use may comprise at least one usual adjuvant for compositions for oral use, in particular chosen from the group formed by surfactants, thickening agents, humectants and polishing agents such as silica, active agents such as fluorides, and in particular sodium fluoride, anti-plaque agents, anti-scale agents, and, optionally, sweetening agents, such as sodium saccharinate.
- the composition can, in particular, be in the form of a mouthwash or toothpaste.
- the present invention also relates to a method of in vivo protection of the mucous membranes, the skin or the hair of a human subject against free radicals involved in oxidation phenomena, in which at least one applies to the substrate to be protected a proanthocyanidin oligomer formed from at least one dimer, trimer or tetramer having an elementary unit corresponding to formula (I), characterized in that the said oligomer (s) is (are) dissolved in a aqueous phase encapsulated in vesicles delimited by a lipid phase membrane consisting of at least one ionic amphiphilic lipid and / or at least one nonionic amphiphilic lipid.
- the preferred lipids are those which have been previously indicated for the compositions according to the invention; the implementation of the process is carried out effectively by application to the substrate to be protected of a composition according to the invention as defined above.
- a night cream can be used which can be used for facial skin care.
- This cream has the following formulation:
- the lipids are mixed at 95 ° C in the molten state.
- the procyanidolic oligomers are dissolved in 10 g of water. This aqueous solution is brought to 80 ° C.
- the aqueous phase is mixed with the lipid phase with gentle stirring with a spatula to form a lamellar phase.
- the rest of the water is then added to constitute the dispersion phase and the mixture is stirred in the "TURRAX" ultra-disperser at a speed of rotation of 10,000 rpm for 15 minutes.
- Conservatives An aqueous dispersion of lipid vesicles having a size of 300 ⁇ 50 nanometers is obtained.
- the product is in the form of a fluid cream.
- Example 1 The cream of Example 1 is used to protect hair exposed to the sun intensively. After shampooing, apply to wet hair 7 g of cream per hair and distribute the cream well over all of the hair. This application is carried out without subsequent rinsing. This treatment is carried out once a week for three months. It is found after this period that the hair has not been altered despite regular exposure to the sun.
- EXAMPLE 3
- Example 2 The same cream is used as in Example 1 for hair care exposed to the sun intensively, but the application is carried out with subsequent rinsing with water. For each application after shampooing, 20 g of cream are used per hair and after having distributed the cream well over wet hair, it is left to stand for 15 minutes. Then rinse with warm water.
- a mouthwash is produced having the following formulation: - Nonionic lipid of formula
- n is an average statistical value equal to 2.7 determined by 1 H NMR at 500 MHz, .
- R is a mixture of radicals C 4H29 and Ci6H33 1.8 g
- This mouthwash is produced according to an operating process analogous to that of Example 1.
- the lipids are melted at 95 ° C .; the oligomers are dissolved in 1 g of water.
- This aqueous solution is mixed with the molten lipids to form a lamellar phase.
- the rest of the water is then added to form the dispersion phase and the mixture is stirred vigorously; finally add the conservatives.
- the vesicles obtained have sizes of the order of 200 ⁇ 50 nanometers.
- This mouthwash is used after brushing the teeth at a rate of 10 ml per application twice a day for a month on a subject with gums sensitive to periodontitis. After the treatment, it is found that the gums appear healthier, no periodontitis having been triggered during the duration of the treatment.
- a mouthwash having the following formulation is produced:
- the lipids are mixed in a water bath at 85 ° C.
- the oligomers are dissolved in 4 g of water. This solution is brought to 85 ° C. and is added in small portions to the molten lipids, with stirring with a spatula.
- the mixture is maintained at 85 ° C. in a water bath for 1 hour to form a lamellar phase.
- the rest of the water is then added at 20 ° C. with vigorous stirring and then the preservatives are added.
- the vesicles obtained have sizes of the order of 350 ⁇ 50 nanometers.
Abstract
Cosmetic or pharmaceutic composition for protecting a person's mucosa, skin or hair from the oxidizing effect of free radicals. Said composition is formed from a vesicle aqueous dispersion, the lipidic membrane consisting of at least one ionic and/or non-ionic amphiphilic lipid. The membrane encapsulates an aqueous phase which contains at least one proanthocyanidin oligomer. Encapsulation of the oligomer reduces tissue staining and improves the active agent's stability.
Description
composition comprenant un ogl lomere proanthocyanldlnlque encapsule dans un l iposomecomposition comprising a proanthocyanldlnlque ogl lomere encapsulated in an iposome
La présente invention concerne une composition cosmétique ou pharmaceutique comprenant un oligomère proanthocyanidinique visant à la protection des muqueuses, de l'épiderme humain et des cheveux contre les radicaux libres impliqués dans des phénomènes d'oxydation ; elle concerne aussi un procédé de protection correspondant.The present invention relates to a cosmetic or pharmaceutical composition comprising a proanthocyanidin oligomer intended for the protection of the mucous membranes, of the human epidermis and of the hair against the free radicals involved in oxidation phenomena; it also relates to a corresponding protection process.
Le rayonnement solaire, la chaleur, la pollution atmosphérique et, notamment, les fumées et le tabac sont connus pour entraîner la formation de radicaux libres. Ces radicaux libres amorcent des réactions de dégradation des lipides, protéines, acides nucléiques, qui sont présents, notamment, dans la peau, les muqueuses et les cheveux. Il est donc apparu particulièrement important de protéger la peau, les muqueuses et les cheveux contre ces radicaux libres et ce, d'autant plus que les compositions cosmétiques de type classique comportent très souvent des constituants sensibles aux radicaux libres et, notamment, des lipides.Solar radiation, heat, atmospheric pollution and, in particular, smoke and tobacco are known to cause the formation of free radicals. These free radicals initiate degradation reactions of lipids, proteins, nucleic acids, which are present, in particular, in the skin, mucous membranes and hair. It therefore appeared particularly important to protect the skin, the mucous membranes and the hair against these free radicals, especially since the cosmetic compositions of conventional type very often contain constituents sensitive to free radicals and, in particular, lipids.
On a déjà indiqué, notamment dans "J.MASQUELIER, Parfums, Cosmétiques et Arômes n° 95 (1990), pages 89-97", que les oligomères procyanidoliques (OPC) sont des agents à forte activité anti¬ radicaux libres, utiles pour des usages médicamenteux et cosmétiques. A cet égard, le brevet EP-A-301 975 décrit des compositions destinées au traitement des maladies parodontales contenant un oligomère procyanidolique. Cette activité antioxydante a également été décrite pour des dérivés substitués proanthocyanidiniques dans le brevet US-A- 4 797 421, qui propose aussi l'utilisation desdits dérivés en cosmétique. Dans cet état de la technique, il est indiqué que l'on préfère les oligomères, qui sont des di-, tri- ou tétra-mères. L'intérêt de ces oligomères antioxydants provient notamment du fait qu'ils sont extraits de diverses plantes et ne sont pas toxiques contrairement aux antioxydants de synthèse, tels que le butyl hydroxy toluène ou le butyl hydroxyanisole. Les procédés d'extraction correspondants ont
notamment été décrits dans FR-A-2 643 073 ou indiqués par référence dans US-A-4 797 421 précité.It has already been indicated, in particular in "J.MASQUELIER, Perfumes, Cosmetics and Aromas No. 95 (1990), pages 89-97", that procyanidolic oligomers (OPC) are agents with strong anti-free radical activity, useful for medicinal and cosmetic uses. In this regard, patent EP-A-301,975 describes compositions intended for the treatment of periodontal diseases containing a procyanidolic oligomer. This antioxidant activity has also been described for proanthocyanidin substituted derivatives in US Pat. No. 4,797,421, which also proposes the use of said derivatives in cosmetics. In this state of the art, it is indicated that the oligomers, which are di-, tri- or tetra-mothers, are preferred. The interest of these antioxidant oligomers stems in particular from the fact that they are extracted from various plants and are not toxic unlike synthetic antioxidants, such as butyl hydroxy toluene or butyl hydroxyanisole. The corresponding extraction processes have in particular have been described in FR-A-2,643,073 or indicated by reference in US-A-4,797,421 mentioned above.
On a malheureusement constaté que l'application de compositions contenant un oligomère procyanidolique ou s proanthocyanidinique présente l'inconvénient de tacher les tissus vivants, les dents ou les vêtements en contact avec la peau traitée par de telles compositions.Unfortunately, it has been found that the application of compositions containing a procyanidolic or proanthocyanidin oligomer has the drawback of staining living tissues, teeth or clothing in contact with the skin treated with such compositions.
On sait, par ailleurs, que certains lipides amphiphiles possèdent la propriété de former des phases mésomorphes, dont l'état 0 d'organisation est intermédiaire entre l'état cristallin et l'état liquide et que, parmi eux, certains sont susceptibles de gonfler en présence d'une solution aqueuse pour former une phase lamellaire puis, après agitation, former des vésicules ou sphérules dispersées dans une phase aqueuse. Ces vésicules sont formées par des feuillets sensiblement 5 concentriques constitués d'une ou plusieurs couches multimoléculaires, de préférence bimoléculaires, encapsulant une phase aqueuse et constituant une membrane lipidique.We also know that certain amphiphilic lipids have the property of forming mesomorphic phases, the state of organization of which is intermediate between the crystalline state and the liquid state and that, among them, some are capable of swelling. in the presence of an aqueous solution to form a lamellar phase and then, after stirring, to form vesicles or spherules dispersed in an aqueous phase. These vesicles are formed by substantially concentric sheets made up of one or more multimolecular layers, preferably bimolecular, encapsulating an aqueous phase and constituting a lipid membrane.
Les vésicules susmentionnées peuvent être préparées par de nombreux procédés. Selon un premier procédé, qui est par exemple 0 décrit par BANGHAM et autres. (J. Mol. Bio., 13, 1965, pages 238 à 262), on dissout la phase lipidique dans un solvant volatil, on forme un film mince de phase lipidique sur les parois d'un flacon par évaporation du solvant, on introduit la phase à encapsuler sur le film lipidique et on agite le mélange mécaniquement jusqu'à obtention de la dispersion de vésicules à la taille désirée ; on obtient ainsi une dispersion aqueuse de vésicules encapsulant une phase aqueuse, la phase aqueuse encapsulée et la phase aqueuse de dispersion étant identiques. Selon un second procédé, décrit par exemple dans FR-A-2 315 991, on prépare la phase lipidique par mélange du (des) lipide(s) amphiphile(s) et des éventuels 0 additifs, à une température où le mélange est fondu, si le mélange n'est pas liquide à température ambiante ; on forme une phase lamellaire, par introduction de la phase aqueuse à encapsuler ; puis on disperse la phase lamellaire sous forme de vésicules, à l'aide d'un ultra-disperseur, d'un homogénéiseur ou d'ultrasons, dans une phase aqueuse de dispersion ; dans une variante de ce procédé, la formation de la phase lamellaire ne constitue pas un stade séparé du procédé. Les vésicules
obtenues par ces deux procédés sont généralement de type "multifeuillets". Pour obtenir des vésicules de type "monofeuillet", on peut utiliser un procédé, qui consiste à solubiliser le mélange lipidique par l'octyl glucoside et à former les vésicules selon l'enseignement de FR-A-2 543 018. Cette énumération de procédés n'est aucunement limitative et l'invention ci-après définie est applicable quelque soit le procédé de fabrication des vésicules.The above-mentioned vesicles can be prepared by many methods. According to a first method, which is for example 0 described by BANGHAM and others. (J. Mol. Bio., 13, 1965, pages 238 to 262), the lipid phase is dissolved in a volatile solvent, a thin film of lipid phase is formed on the walls of a bottle by evaporation of the solvent, we introduce the phase to be encapsulated on the lipid film and the mixture is stirred mechanically until the dispersion of vesicles of the desired size is obtained; an aqueous dispersion of vesicles encapsulating an aqueous phase is thus obtained, the encapsulated aqueous phase and the aqueous dispersion phase being identical. According to a second method, described for example in FR-A-2 315 991, the lipid phase is prepared by mixing the amphiphilic lipid (s) and any additives, at a temperature where the mixture is melted , if the mixture is not liquid at room temperature; a lamellar phase is formed by introducing the aqueous phase to be encapsulated; then the lamellar phase is dispersed in the form of vesicles, using an ultra-disperser, a homogenizer or ultrasound, in an aqueous dispersion phase; in a variant of this process, the formation of the lamellar phase does not constitute a separate stage of the process. The vesicles obtained by these two processes are generally of the "multi-sheet" type. To obtain vesicles of the "single-sheet" type, a process can be used, which consists in dissolving the lipid mixture with octyl glucoside and in forming the vesicles according to the teaching of FR-A-2,543,018. This list of processes is in no way limiting and the invention defined below is applicable whatever the process of manufacturing the vesicles.
Selon la présente invention, on a trouvé que la formulation d' oligomères proanthocyanidiniques dans des vésicules de lipides amphiphiles permettait de diminuer le tâchage des tissus vivants, des dents ou des vêtements en contact avec la peau traitée, tout en maintenant au moins au même niveau l'activité anti-radicaux libres de l'agent actif. De plus, on observe une meilleure stabilité de l'agent actif lorsqu'il est inclus dans des vésicules de lipides amphiphiles, ce qui permet une meilleure conservation dans le temps des compositions vis- à-vis de la péroxydation des lipides ainsi qu'une meilleure conservation dans le temps des propriétés anti-radicaux libres des oligomères proanthocyanidiniques encapsulés dans les vésicules.According to the present invention, it has been found that the formulation of proanthocyanidin oligomers in vesicles of amphiphilic lipids makes it possible to reduce the staining of living tissues, teeth or clothing in contact with the treated skin, while maintaining at least at the same level. anti-free radical activity of the active agent. In addition, better stability of the active agent is observed when it is included in amphiphilic lipid vesicles, which allows better preservation over time of the compositions with respect to lipid peroxidation as well as better preservation over time of the anti-free radical properties of the proanthocyanidin oligomers encapsulated in the vesicles.
La présente invention a donc pour objet une composition cosmétique ou pharmaceutique pour protéger les muqueuses, la peau ou les cheveux d'un sujet humain contre les radicaux libres impliqués dans des phénomènes d'oxydation, ladite composition renfermant au moins un oligomère proanthocyanidinique formé d'au moins un dimère, trimère ou tétramère ayant un motif élémentaire correspondant à la formule :The subject of the present invention is therefore a cosmetic or pharmaceutical composition for protecting the mucous membranes, the skin or the hair of a human subject against free radicals involved in oxidation phenomena, said composition containing at least one proanthocyanidin oligomer formed from at least one dimer, trimer or tetramer having an elementary unit corresponding to the formula:
Selon l'invention, on préfère utiliser les oligomères, dont le motif élémentaire de formule (I) correspond au cas où R et R4 représentent l'hydrogène et R2 et R3 représentent un groupe hydroxyle.According to the invention, it is preferred to use the oligomers, the elementary unit of formula (I) of which corresponds to the case where R and R4 represent hydrogen and R2 and R3 represent a hydroxyl group.
A titre purement illustratif et non limitatif, on peut indiquer que les oligomères utilisés dans les compositions selon l'invention peuvent être extraits d'au moins un végétal choisi dans le groupe formé par : - les feuilles de vigne rouge (produit vendu sous le nom commercial de "OPC PRECIPITES VIGNE ROUGE" par la société "ADFBy way of illustration only and without limitation, it may be indicated that the oligomers used in the compositions according to the invention can be extracted from at least one plant chosen from the group formed by: - red vine leaves (product sold under the name sales of "OPC PRECIPITES VIGNE ROUGE" by the company "ADF
CHIMIE"),CHEMISTRY"),
- les pépins de raisin (produit vendu sous le nom commercial de "OPC DE RAISIN LYOPHILISES" par la société "ADF CHIMIE"), - un mélange de feuilles de vigne rouge et de pépins de raisin- grape seeds (product sold under the trade name "OPC DE RAISIN LYOPHILISES" by the company "ADF CHIMIE"), - a mixture of red vine leaves and grape seeds
(produit vendu sous le nom commercial de "OPC NEBULISES T 20 VIGNE ROUGE/RAISIN" par la société "ADF CHIMIE"),(product sold under the trade name of "OPC NEBULISES T 20 VIGNE ROUGE / RAISIN" by the company "ADF CHIMIE"),
- l'écorce de pin,- pine bark,
- un mélange écorce de pin et pépins de raisin (produit vendu sous le nom commercial de "BIOFLAVANES" par la société "DRT"),- a mixture of pine bark and grape seeds (product sold under the trade name "BIOFLAVANES" by the company "DRT"),
- les bractées de tilleul (produit vendu sous le nom commercial de "OPC PRECIPITES TILLEUL" par la société "ADF CHIMIE"),- linden bracts (product sold under the trade name "OPC PRECIPITES TILLEUL" by the company "ADF CHIMIE"),
- les feuilles de noisetier,- hazelnut leaves,
- l'écorce de quinquina, - les fleurs d'aubépine (produit vendu sous le nom commercial de- cinchona bark, - hawthorn flowers (product sold under the trade name of
"OPC PRECIPITES AUBEPINE" par la société "ADF CHIMIE"),
- la racine de rhubarbe."OPC PRECIPITES AUBEPINE" by the company "ADF CHIMIE"), - rhubarb root.
Comme source d' oligomères pour les compositions selon l'invention, on peut aussi utiliser les produits définis dans la demande de brevet européen 348 781. Selon l'invention, tous les lipides amphiphiles ioniques et/ou non-ioniques susceptibles de former des vésicules stables, seuls ou en mélange avec des additifs ayant pour fonction de diminuer la perméabilité des membranes des vésicules et d'améliorer leur stabilité, peuvent être utilisés pour constituer les membranes lipidiques des vésicules des compositions selon l'invention. La phase lipidique constitutive des membranes des vésicules de la composition selon l'invention peut donc comprendre, de façon connue, au moins un lipide choisi dans le groupe formé par :As a source of oligomers for the compositions according to the invention, it is also possible to use the products defined in European patent application 348 781. According to the invention, all the ionic and / or non-ionic amphiphilic lipids capable of forming vesicles stable, alone or in admixture with additives having the function of reducing the permeability of the membranes of the vesicles and of improving their stability, can be used to constitute the lipid membranes of the vesicles of the compositions according to the invention. The lipid phase constituting the membranes of the vesicles of the composition according to the invention can therefore comprise, in a known manner, at least one lipid chosen from the group formed by:
A) les lipides non-ioniques ci-après définis : (1) les dérivés du glycérol, linéaires ou ramifiés, de formuleA) the nonionic lipids defined below: (1) glycerol derivatives, linear or branched, of formula
-C3H5(OH)0- est représenté par les structures suivantes prises en mélange ou séparément :-C 3 H 5 (OH) 0- is represented by the following structures, taken as a mixture or separately:
-CH2CH0HCH20- t - CH2- CH0- , _ CH-CH20--CH 2 CH0HCH 2 0- t - CH 2 - CH0-, _ CH-CH 2 0-
CH20H CH20HCH 2 0H CH 2 0H
. q est une valeur statistique moyenne comprise entre 1 et 6 ou bien q = 1 ou 2 et alors -C3H5(OH)0- est représenté par la structure -CH2CHOH-CH2O- ;. q is an average statistical value between 1 and 6 or q = 1 or 2 and then -C3H5 (OH) 0- is represented by the structure -CH2CHOH-CH2O-;
. RQ représente : (a) une chaîne aliphatique, linéaire ou ramifiée saturée ou insaturée, contenant de 12 à 30 atomes de carbone ; ou des radicaux hydrocarbonés des alcools de lanoline ; ou les restes d'alpha-diols à longue chaîne ;
(b) un reste R2lCO, où R21 est un radical aliphatique, linéaire ou ramifié, en C11-C29 ;. R Q represents: (a) an aliphatic chain, linear or branched saturated or unsaturated, containing from 12 to 30 carbon atoms; or hydrocarbon radicals of lanolin alcohols; or the remains of long-chain alpha-diols; (b) a residue R 2 lCO, where R21 is a C11-C29 aliphatic radical, linear or branched;
(c) un reste(c) a remainder
. R17 peut prendre la signification (a) ou (b) donnée pour. R17 can take the meaning (a) or (b) given for
Ro »Ro »
. -OC2H3(R23)- est représenté par les structures suivantes, prises en mélange ou séparément :. -OC 2 H 3 (R 2 3) - is represented by the following structures, taken as a mixture or separately:
-0CH- CH2- et -0-CH2-CH--0CH- CH 2 - and -0-CH 2 -CH-
où R23 prend la signification (a) donnée pour RQ -where R23 takes the meaning (a) given for R Q -
(2) les éthers de polyglycérol, linéaires ou ramifiés, comportant deux chaînes grasses ; (3) les diols à chaîne grasse ;(2) polyglycerol ethers, linear or branched, comprising two fatty chains; (3) fatty chain diols;
(4) les alcools gras oxyéthylénés ou non, les stérols tels par exemple le cholestérol et les phytostérols oxyéthylénés ou non ;(4) fatty alcohols oxyethylenated or not, sterols such as for example cholesterol and phytosterols oxyethylenated or not;
(5) les éthers et esters de polyols, oxyéthylénés ou non, l'enchaînement des oxydes d'éthylène pouvant être linéaire ou cyclique ; (6) les glycolipides d'origine naturelle ou synthétique, les éthers et esters de mono ou polysaccharides et notamment les éthers et les esters de glucose ; (7) les hydroxyamides décrits dans le brevet français n° 2 588 256 et représentés par la formule :(5) ethers and esters of polyols, oxyethylenated or not, the chain of ethylene oxides being able to be linear or cyclic; (6) glycolipids of natural or synthetic origin, ethers and esters of mono or polysaccharides and in particular ethers and esters of glucose; (7) the hydroxyamides described in French Patent No. 2,588,256 and represented by the formula:
R 24- CH0H-CH-C0A ttZH)R 2 4- CH0H-CH-C0A ttZH)
R5— CONH formule (VII) dans laquelle :R 5 - CONH formula (VII) in which:
- R24 désigne un radical al yle ou alcényle en C7-C21 ;- R24 denotes an al yl or C7-C21 alkenyl radical;
- R5 désigne un radical hydrocarboné, saturé ou insaturé, en C7-C31
COA désigne un groupement choisi parmi les deux groupements suivants . un reste- R5 denotes a hydrocarbon radical, saturated or unsaturated, C7-C31 COA designates a group chosen from the following two groups. a rest
CON-B ICON-B I
ou :or :
. B est un radical alcoyle dérivé d'aminés primaires ou secondaires, mono- ou polyhydroxylées ; et . R désigne un atome d'hydrogène ou un radical méthyle, éthyle ou hydroxyéthyle ; et . un reste -COOZ, où Z représente le reste d'un polyol en C3-C7.. B is an alkyl radical derived from primary or secondary, mono- or polyhydroxylated amines; and. R denotes a hydrogen atom or a methyl, ethyl or hydroxyethyl radical; and. a residue -COOZ, where Z represents the remainder of a C3-C7 polyol.
(8) les céramides naturels ou de synthèse ;(8) natural or synthetic ceramides;
(9) les dihydroxyalky lamines, les aminés grasses oxyéthylénées ;(9) dihydroxyalky lamines, fatty oxyethylenated amines;
B) les lipides amphiphiles ioniques ci-après définis : (1) les lipides amphiphiles anioniques tels que : • les phospholipides naturels, notamment la lécithine d'oeuf ou de soja, ou la sphingomyéline, les phospholipides modifiés par voie chimique ou enzymatique, notamment la lécithine hydrogénée, et les phospholipides de synthèse, notamment la dipalmitoylphosphatidyl- choline ; • des composés anioniques, tels que ceux décrits dans le brevet français n° 2 588 256 et représentés par la formule :B) the ionic amphiphilic lipids defined below: (1) anionic amphiphilic lipids such as: • natural phospholipids, in particular egg or soy lecithin, or sphingomyelin, phospholipids modified by chemical or enzymatic means, in particular hydrogenated lecithin, and synthetic phospholipids, including dipalmitoylphosphatidylcholine; • anionic compounds, such as those described in French Patent No. 2,588,256 and represented by the formula:
. Rg représente un radical alkyle ou alcényle en C7-C21 . R9 représente un radical hydrocarboné, saturé ou insaturé en C7-C31, et. Rg represents a C7-C21 alkyl or alkenyl radical. R9 represents a C7-C31 saturated or unsaturated hydrocarbon radical, and
. M représente H, Na, K, NH4 ou un ion ammonium substitué dérivé d'une aminé ;
(2) des composés anioniques, tels que les esters phosphoriques d'alcools gras, par exemple le dicétylphosphate et le dimyristylphosphate sous forme d'acides ou de sels alcalins ; l'acide heptylnonylbenzène sulfonique ; le sulfate de cholestérol acide et ses sels alcalins et le phosphate de cholestérol acide et ses sels alcalins ; les lysolécithines ; les alkylsulfates, par exemple le cétyl sulfate de sodium ; les gangliosides ;. M represents H, Na, K, NH4 or a substituted ammonium ion derived from an amine; (2) anionic compounds, such as the phosphoric esters of fatty alcohols, for example diketylphosphate and dimyristylphosphate in the form of acids or alkaline salts; heptylnonylbenzene sulfonic acid; acid cholesterol sulfate and its alkali salts and acid cholesterol phosphate and its alkali salts; lysolecithins; alkyl sulfates, for example sodium cetyl sulfate; gangliosides;
(3) les lipides amphiphiles cationiques, tels que :(3) cationic amphiphilic lipids, such as:
• les composés cationiques dérivés ammonium quaternaire répondant à la formule :• cationic compounds derived from quaternary ammonium corresponding to the formula:
• les aminés à longue chaîne et leurs dérivés ammonium quaternaire, les esters d'aminoalcools à longue chaîne et leurs sels et dérivés ammonium quaternaire ;• long chain amines and their quaternary ammonium derivatives, long chain amino alcohol esters and their salts and quaternary ammonium derivatives;
• des lipides polymérisables, comme ceux décrits par Ringsdorf et autres dans "Angewandte Chemie", vol 27, n°l, Janvier 1988, pages• polymerizable lipids, such as those described by Ringsdorf and others in "Angewandte Chemie", vol 27, n ° l, January 1988, pages
129 et 137.129 and 137.
On peut ajouter à la phase lipidique constituant la membrane des vésicules, des additifs non-lipidiques tels que certains polymères comme, par exemple, les polypeptides et les protéines. Les lipides amphiphiles utilisés représentent ensemble, de préférence de 1 àNon-lipid additives such as certain polymers such as, for example, polypeptides and proteins, can be added to the lipid phase constituting the membrane of the vesicles. The amphiphilic lipids used together represent, preferably from 1 to
95 %, plus particulièrement de 10 à 80 %, du poids total de la phase lipidique vésiculaire.95%, more particularly from 10 to 80%, of the total weight of the vesicular lipid phase.
La dispersion aqueuse de la composition selon l'invention comporte une phase aqueuse de dispersion, qui peut être constituée par de l'eau, ou un mélange d'eau et d'au moins un solvant miscible à
l'eau, tels que les alcools en C1-C7 et les polyols d' alkyle en C1-C5.The aqueous dispersion of the composition according to the invention comprises an aqueous dispersion phase, which may consist of water, or a mixture of water and at least one solvent miscible with water, such as C1-C7 alcohols and C1-C5 alkyl polyols.
La phase aqueuse de dispersion peut également contenir des composés en solution, tels que des sucres, des sels organiques ou minéraux ou des polymères. La concentration en phase lipidique totale dans la composition est comprise entre 0,01 % et 50 % en poids, de préférence entre 1 % et 20 % en poids par rapport au poids total de la composition. Les vésicules dispersées ont des dimensions comprises entre 20 et 3000 nm, de préférence entre 20 et 500 nm. La concentration totale en oligomère(s) proanthocyanidinique(s) dans la composition est comprise entre 0,01 et 2 % en poids par rapport au poids total de la composition.The aqueous dispersion phase can also contain compounds in solution, such as sugars, organic or mineral salts or polymers. The concentration in total lipid phase in the composition is between 0.01% and 50% by weight, preferably between 1% and 20% by weight relative to the total weight of the composition. The dispersed vesicles have dimensions between 20 and 3000 nm, preferably between 20 and 500 nm. The total concentration of proanthocyanidin oligomer (s) in the composition is between 0.01 and 2% by weight relative to the total weight of the composition.
Selon un mode de réalisation particulier, la phase aqueuse de dispersion peut aussi contenir une dispersion de gouttelettes d'un liquide non-miscible à l'eau, que les vésicules stabilisent. Par conséquent, en présence de vésicules de lipides amphiphiles ioniques et/ou de lipides amphiphiles non-ioniques, il n'est pas nécessaire d'introduire un émulsionnant usuel tel que le monostéarate de glycérol. Les gouttelettes d'une telle dispersion ont généralement des tailles comprises entre 100 et 10 000 nm.According to a particular embodiment, the aqueous dispersion phase can also contain a dispersion of droplets of a liquid immiscible with water, which the vesicles stabilize. Consequently, in the presence of vesicles of ionic amphiphilic lipids and / or nonionic amphiphilic lipids, it is not necessary to introduce a usual emulsifier such as glycerol monostearate. The droplets of such a dispersion generally have sizes between 100 and 10,000 nm.
Le liquide non-miscible à l'eau, qui peut être présent sous forme de dispersion de gouttelettes dans la phase aqueuse de dispersion, peut notamment être :The water-immiscible liquid, which can be present in the form of a dispersion of droplets in the aqueous dispersion phase, can in particular be:
- une huile animale ou végétale formée par des esters d'acide gras et de polyols, en particulier les triglycérides liquides, par exemple choisis dans le groupe formé par les huiles de tournesol, de maïs, de soja, de courge, de pépins de raisin, de jojoba, de sésame, de noisette, les huiles de poisson, le tricaprocaprylate de glycérol, ou une huile végétale ou animale de formule R19COOR2O:. formule dans laquelle Ri 9 représente le reste d'un acide gras supérieur comportant de 7 à 19 atomes de carbone et R20 représente une chaîne hydrocarbonée ramifiée contenant de 3 à 20 atomes de carbone, par exemple l'huile de Purcellin ;- an animal or vegetable oil formed by fatty acid and polyol esters, in particular liquid triglycerides, for example chosen from the group formed by sunflower, corn, soya, squash, grapeseed oils , jojoba, sesame, hazelnut, fish oils, glycerol tricaprocaprylate, or a vegetable or animal oil of formula R19COOR2O :. formula in which Ri 9 represents the remainder of a higher fatty acid containing from 7 to 19 carbon atoms and R20 represents a branched hydrocarbon chain containing from 3 to 20 carbon atoms, for example Purcellin oil;
- des huiles essentielles naturelles ou synthétiques telles que, par exemple, les huiles d'eucalyptus, de lavandin, de lavande, de vétiver, de litsea cubeba, de citron, de santal, de romarin, de camomille, de
sarriette, de noix de muscade, de cannelle, d'hysope, de carvi, d'orange, de géraniol et de cade ;- natural or synthetic essential oils such as, for example, oils of eucalyptus, lavandin, lavender, vetiver, litsea cubeba, lemon, sandalwood, rosemary, chamomile, savory, nutmeg, cinnamon, hyssop, caraway, orange, geraniol and cade;
- des hydrocarbures, tels que l'hexadécane et l'huile de paraffine ; - des carbures halogènes, notamment des fluorocarbures tels que des fluoroamines par exemple la perfluorotributy lamine, des hydrocarbures fluorés, par exemple le perfluorodécahydronaphtalène, des fluoroesters et des fluoroéthers ;- hydrocarbons, such as hexadecane and paraffin oil; - halogenated carbides, in particular fluorocarbons such as fluoroamines, for example perfluorotributy lamin, fluorinated hydrocarbons, for example perfluorodecahydronaphthalene, fluoroesters and fluoroethers;
- des silicones, par exemple les polysiloxanes, les polydiméthylsiloxanes et les fluorosilicones ;- silicones, for example polysiloxanes, polydimethylsiloxanes and fluorosilicones;
- des esters d'acide minéral et d'un alcool ;- esters of mineral acid and of an alcohol;
- des éthers et des poly éthers.- ethers and polyethers.
La composition selon l'invention peut se présenter sous forme de lotion, de lotion épaissie, de gel, de crème, de sérum, de lait, de pommade, de bâtonnet solide, de mousse ou de spray.The composition according to the invention can be in the form of a lotion, thickened lotion, gel, cream, serum, milk, ointment, solid stick, foam or spray.
La composition selon l'invention peut, en outre, contenir au moins un adjuvant cosmétique choisi dans le groupe formé par les corps gras, les solvants organiques, les silicones, les épaississants, les adoucissants, les filtres solaires UV-A, UV-B ou à bande large, les agents autobronzants, les agents antimousse, les agents hydratants, les parfums, les conservateurs, les bactéricides, les agents antipelliculaires, les agents antichutes, les agents antioxydants, les agents antiséborrhéiques, les agents cicatrisants, les agents antimicrobiens, les tensioactifs, les charges, les séquestrants, les polymères anioniques, cationiques, non-ioniques, amphotères ou leurs mélanges, les propulseurs, les agents alcalinisants ou acidifiants, les colorants, les agents nacrants et les pigments d'oxyde métallique.The composition according to the invention may, in addition, contain at least one cosmetic adjuvant chosen from the group formed by fatty substances, organic solvents, silicones, thickeners, softeners, sun filters UV-A, UV-B or broadband, self-tanning agents, anti-foaming agents, moisturizing agents, perfumes, preservatives, bactericides, anti-dandruff agents, anti-hair loss agents, antioxidant agents, antiseborrhoeic agents, healing agents, antimicrobial agents, surfactants, fillers, sequestrants, anionic, cationic, nonionic, amphoteric polymers or their mixtures, propellants, basifying or acidifying agents, dyes, pearlescent agents and metal oxide pigments.
Lorsque la composition selon l'invention est utilisée pour la protection de l'épiderme humain contre les radicaux libres, elle peut efficacement se présenter sous la forme d'une crème, d'un lait, d'une pommade, d'un gel, d'un bâtonnet solide ou d'une mousse aérosol.When the composition according to the invention is used for the protection of the human epidermis against free radicals, it can effectively be in the form of a cream, a milk, an ointment, a gel, a solid stick or aerosol foam.
Lorsque la composition selon l'invention est utilisée pour la protection des cheveux, elle peut se présenter sous forme de shampooing, de lotion, de gel, de composition à rincer, à appliquer avant ou après shampooing, avant ou après coloration ou décoloration, avant, pendant ou après permanente ou défrisage, de lotion ou gel
coiffant ou traitant, de lotion ou gel pour le brushing ou la mise en plis, de laque pour cheveux, de composition de permanente ou de défrisage, de coloration ou décoloration des cheveux.When the composition according to the invention is used for protecting the hair, it may be in the form of shampoo, lotion, gel, rinse-out composition, to be applied before or after shampooing, before or after coloring or bleaching, before , during or after permanent or straightening, lotion or gel styling or treating, lotion or gel for brushing or styling, hairspray, composition for permanent or straightening, coloring or bleaching of hair.
Lorsque la composition selon l'invention est utilisée comme produit de maquillage des cils, des sourcils ou de la peau, tel que crème de traitement de l'épiderme, fond de teint, bâton de rouge à lèvres, fard à paupières, fard à joues, ligneur encore appelé "eye liner" ou mascara, elle peut se présenter sous forme pâteuse ou aqueuse.When the composition according to the invention is used as a makeup product for the eyelashes, the eyebrows or the skin, such as an epidermis treatment cream, foundation, lipstick stick, eyeshadow, blush , liner also called "eye liner" or mascara, it can be in pasty or aqueous form.
Lorsque la composition selon l'invention est utilisée dans une application bucco-dentaire, elle peut comprendre au moins un adjuvant usuel pour les compositions à usage buccal, notamment choisi dans le groupe formé par des agents tensioactifs, des agents épaississants, des agents humectants et des agents de polissage tels que la silice, des agents actifs comme des fluorures, et en particulier le fluorure de sodium, des agents antiplaque, des agents antitartre, et, éventuellement, des agents édulcorants, comme le saccharinate de sodium. La composition peut, notamment, se présenter sous forme de bain de bouche ou de dentifrice.When the composition according to the invention is used in an oral application, it may comprise at least one usual adjuvant for compositions for oral use, in particular chosen from the group formed by surfactants, thickening agents, humectants and polishing agents such as silica, active agents such as fluorides, and in particular sodium fluoride, anti-plaque agents, anti-scale agents, and, optionally, sweetening agents, such as sodium saccharinate. The composition can, in particular, be in the form of a mouthwash or toothpaste.
La présente invention a également pour objet un procédé de protection in vivo des muqueuses, de la peau ou des cheveux d'un sujet humain contre les radicaux libres impliqués dans des phénomènes d'oxydation, dans lesquels on applique sur le substrat à protéger au moins un oligomère proanthocyanidinique formé d'au moins un dimère, trimère ou tétramère ayant un motif élémentaire correspondant à la formule (I), caractérisé par le fait que le(s)dit(s) oligomère(s) est(sont) dissous dans une phase aqueuse encapsulée dans des vésicules délimitées par une membrane de phase lipidique constituée d'au moins un lipide amphiphile ionique et/ou d'au moins un lipide amphiphile non-ionique. Pour la mise en oeuvre du procédé ci-dessus défini, les lipides préférés sont ceux qui ont été précédemment indiqués pour les compositions selon l'invention ; la mise en oeuvre du procédé s'effectue efficacement par application sur le substrat à protéger d'une composition selon l'invention telle que ci-dessus définie. Pour mieux faire comprendre l'objet de l'invention, on va en décrire maintenant à titre d'exemples plusieurs modes de réalisation.
EXEMPLE 1The present invention also relates to a method of in vivo protection of the mucous membranes, the skin or the hair of a human subject against free radicals involved in oxidation phenomena, in which at least one applies to the substrate to be protected a proanthocyanidin oligomer formed from at least one dimer, trimer or tetramer having an elementary unit corresponding to formula (I), characterized in that the said oligomer (s) is (are) dissolved in a aqueous phase encapsulated in vesicles delimited by a lipid phase membrane consisting of at least one ionic amphiphilic lipid and / or at least one nonionic amphiphilic lipid. For the implementation of the process defined above, the preferred lipids are those which have been previously indicated for the compositions according to the invention; the implementation of the process is carried out effectively by application to the substrate to be protected of a composition according to the invention as defined above. To better understand the object of the invention, several embodiments will now be described by way of examples. EXAMPLE 1
On réalise une crème de nuit utilisable pour les soins de la peau de visage. Cette crème a la formulation suivante :A night cream can be used which can be used for facial skin care. This cream has the following formulation:
- Alcool cétylique polyglycérolé (produit vendu sous le nom commercial- Cetyl polyglycerol alcohol (product sold under the trade name
"CHIMEXANE NL" par la société "CHIMEX") 2,375 g"CHIMEXANE NL" by the company "CHIMEX") 2,375 g
- Cholestérol 2,375 g- Cholesterol 2,375 g
- Stéaryl glutamate monosodique (vendu sous le nom commercial " ACYL GLUTAMATE HS 11 " par la société- Monosodium stearyl glutamate (sold under the trade name "ACYL GLUTAMATE HS 11" by the company
"AJINOMOTO") 0,250 g"AJINOMOTO") 0.250 g
- Oligomères procyanidoliques extraits des pépins de raisin (vendus sous le nom commercial "OPC DE RAISIN LYOPHILISES" par la société " ADF CHIMIE") 1,00 g- Procyanidolic oligomers extracted from grape seeds (sold under the trade name "OPC DE RAISIN LYOPHILISES" by the company "ADF CHIMIE") 1.00 g
- Conservateurs 0,20 g- Preservatives 0.20 g
- Eau qsp 100 g- Water qs 100 g
Cette crème est obtenue selon le processus suivant :This cream is obtained according to the following process:
On mélange les lipides à 95 °C à l'état fondu. On met les oligomères procyanidoliques en solution dans 10 g d'eau. On porte cette solution aqueuse à 80 °C. On mélange la phase aqueuse à la phase lipidique sous faible agitation à la spatule pour former une phase lamellaire. On ajoute alors le reste de l'eau pour constituer la phase de dispersion et on agite le mélange à l'ultra-disperseur "TURRAX" à une vitesse de rotation de 10 000 t/mn pendant 15 minutes. On ajoute enfin les conservateurs. On obtient une dispersion aqueuse de vésicules lipidiques ayant une taille de 300 ± 50 nanomètres. Le produit se présente sous la forme d'une crème fluide.The lipids are mixed at 95 ° C in the molten state. The procyanidolic oligomers are dissolved in 10 g of water. This aqueous solution is brought to 80 ° C. The aqueous phase is mixed with the lipid phase with gentle stirring with a spatula to form a lamellar phase. The rest of the water is then added to constitute the dispersion phase and the mixture is stirred in the "TURRAX" ultra-disperser at a speed of rotation of 10,000 rpm for 15 minutes. Finally, we add the Conservatives. An aqueous dispersion of lipid vesicles having a size of 300 ± 50 nanometers is obtained. The product is in the form of a fluid cream.
Cette crème est appliquée sur la peau du visage une fois par jour pendant un mois à raison de 1 g par application. Après cette période de traitement, on constate que la peau est plus souple et le teint plus clair qu'avant traitement. EXEMPLE 2This cream is applied to the skin of the face once a day for a month at a rate of 1 g per application. After this treatment period, we find that the skin is more supple and the complexion lighter than before treatment. EXAMPLE 2
On utilise la crème de l'exemple 1 pour protéger des cheveux exposés au soleil de façon intensive.
Après un shampooing, on applique sur cheveux mouillés 7 g de crème par chevelure et on répartit bien la crème sur l'ensemble des cheveux. Cette application est effectuée sans rinçage ultérieur. Ce traitement est effectuée une fois par semaine pendant trois mois. On constate après cette période que les cheveux n'ont pas été altérés malgré l'exposition régulière au soleil. EXEMPLE 3The cream of Example 1 is used to protect hair exposed to the sun intensively. After shampooing, apply to wet hair 7 g of cream per hair and distribute the cream well over all of the hair. This application is carried out without subsequent rinsing. This treatment is carried out once a week for three months. It is found after this period that the hair has not been altered despite regular exposure to the sun. EXAMPLE 3
On utilise la même crème que dans l'exemple 1 pour les soins de cheveux exposés au soleil de façon intensive, mais l'application s'effectue avec rinçage ultérieur à l'eau. Pour chaque application après shampooing, on utilise 20 g de crème par chevelure et après avoir bien réparti la crème sur les cheveux mouillés, on laisse poser pendant 15 minutes. On rince ensuite à l'eau tiède.The same cream is used as in Example 1 for hair care exposed to the sun intensively, but the application is carried out with subsequent rinsing with water. For each application after shampooing, 20 g of cream are used per hair and after having distributed the cream well over wet hair, it is left to stand for 15 minutes. Then rinse with warm water.
On effectue ce traitement 1 fois par semaine pendant trois mois et l'on obtient le même effet bénéfique que dans l'exemple 2. EXEMPLE 4This treatment is carried out once a week for three months and the same beneficial effect is obtained as in Example 2. EXAMPLE 4
On réalise un bain de bouche ayant la formulation suivante : - Lipide non ionique de formuleA mouthwash is produced having the following formulation: - Nonionic lipid of formula
. — C3H5 (0H) 0- est constitué par un mélange de radicaux :. - C 3 H 5 (0H) 0- consists of a mixture of radicals:
-0-CH- CH?— et — 0-CH?- CH — ï R R --0-CH- CH? - and - 0-CH ? - CH - ï RR -
. n est une valeur statistique moyenne égale à 2,7 déterminée par RMN'H à 500 MHz,
. R est un mélange de radicaux C 4H29 et Ci6H33 1,8 g. n is an average statistical value equal to 2.7 determined by 1 H NMR at 500 MHz, . R is a mixture of radicals C 4H29 and Ci6H33 1.8 g
- Stéaryl glutamate monosodique (vendu sous le nom commercial " ACYLGLUTAMATE HS 11" par la société "AJINOMOTO") 0,2 g- Monosodium stearyl glutamate (sold under the trade name "ACYLGLUTAMATE HS 11" by the company "AJINOMOTO") 0.2 g
- Oligomères procyanidoliques de fleur d'aubépine (vendus sous le nom commercial de "OPC PRECIPITES AUBEPINE" par la société "ADF- Prokyanidolic oligomers of hawthorn flower (sold under the trade name of "OPC PRECIPITES AUBEPINE" by the company "ADF
CHIMIE'') 0,1 g - Conservateurs 0,15 gCHEMISTRY '') 0.1 g - Preservatives 0.15 g
- Eau qsp 100 g- Water qs 100 g
Ce bain de bouche est fabriqué selon un processus opératoire analogue à celui de l'exemple 1. On fond les lipides à 95 °C ; on dissout les oligomères dans 1 g d'eau. On mélange cette solution aqueuse aux lipides fondus pour former une phase lamellaire.This mouthwash is produced according to an operating process analogous to that of Example 1. The lipids are melted at 95 ° C .; the oligomers are dissolved in 1 g of water. This aqueous solution is mixed with the molten lipids to form a lamellar phase.
On ajoute ensuite le reste de l'eau pour former la phase de dispersion et on agite énergiquement ; on ajoute enfin les conservateurs. Les vésicules obtenues ont des tailles de l'ordre de 200 ± 50 nanomètres.The rest of the water is then added to form the dispersion phase and the mixture is stirred vigorously; finally add the conservatives. The vesicles obtained have sizes of the order of 200 ± 50 nanometers.
Ce bain de bouche est utilisé après brossage des dents à raison de 10 ml par application deux fois par jour pendant un mois sur un sujet ayant des gencives sensibles aux parodontites. Après le traitement, on constate que les gencives paraissent plus saines, aucune parodontite ne s 'étant déclenchée pendant la durée du traitement. EXEMPLE S On réalise un bain de bouche ayant la formulation suivante :This mouthwash is used after brushing the teeth at a rate of 10 ml per application twice a day for a month on a subject with gums sensitive to periodontitis. After the treatment, it is found that the gums appear healthier, no periodontitis having been triggered during the duration of the treatment. EXAMPLE S A mouthwash having the following formulation is produced:
- Lécithine de soja hydrogénée (vendue sous le nom commercial "LECINOL S 10" par la société "NIKKO") 1,2 g - Phytostérol oxyéthyléné (vendu sous le nom commercial "GENEROL 122 E5" par la société "HENKEL") 0,8 g- Hydrogenated soy lecithin (sold under the trade name "LECINOL S 10" by the company "NIKKO") 1.2 g - Oxyethylenated phytosterol (sold under the trade name "GENEROL 122 E5" by the company "HENKEL") 0, 8 g
- Oligomères procyanidoliques de fleur d'aubépine (vendus sous le nom commercial "OPC PRECIP-rrES AUBEPINE" par la société "ADF- Procyanidolic oligomers of hawthorn flower (sold under the trade name "OPC PRECIP-rrES AUBEPINE" by the company "ADF
CHIMIE") 0,1 g
- Conservateurs 0,1 gCHEMISTRY ") 0.1 g - Preservatives 0.1 g
- Eau qsp 100 g- Water qs 100 g
Pour obtenir ce bain de bouche, on mélange les lipides au bain marie à 85 °C. On dissout les oligomères dans 4 g d'eau. On porte cette solution à 85° C et on l'ajoute par petites fractions dans les lipides fondus, sous agitation à la spatule. On maintient le mélange à 85° C au bain marie pendant 1 heure pour former une phase lamellaire. On ajoute ensuite le reste de l'eau à 20°C sous forte agitation puis on ajoute les conservateurs. Les vésicules obtenues ont des tailles de l'ordre de 350 ± 50 nanomètres.To obtain this mouthwash, the lipids are mixed in a water bath at 85 ° C. The oligomers are dissolved in 4 g of water. This solution is brought to 85 ° C. and is added in small portions to the molten lipids, with stirring with a spatula. The mixture is maintained at 85 ° C. in a water bath for 1 hour to form a lamellar phase. The rest of the water is then added at 20 ° C. with vigorous stirring and then the preservatives are added. The vesicles obtained have sizes of the order of 350 ± 50 nanometers.
L'application de ce bain de bouche s'effectue comme dans l'exemple 4 et donne les mêmes résultats bénéfiques.
The application of this mouthwash is carried out as in Example 4 and gives the same beneficial results.
Claims
REVENDICATIONS
1 - Composition cosmétique ou pharmaceutique pour protéger les muqueuses, la peau ou les cheveux d'un sujet humain contre les radicaux libres impliqués dans des phénomènes d'oxydation, ladite composition renfermant au moins un oligomère proanthocyanidinique formé d'au moins un dimère, trimère ou tétramère ayant un motif élémentaire correspondant à la formule1 - Cosmetic or pharmaceutical composition for protecting the mucous membranes, skin or hair of a human subject against free radicals involved in oxidation phenomena, said composition containing at least one proanthocyanidin oligomer formed of at least one dimer, trimer or tetramer having an elementary unit corresponding to the formula
2 - Composition selon la revendication 1 , caractérisée par le fait que le(s) oligomère(s), dont le motif élémentaire répond à la formule (I), correspond(ent) au cas où Ri et R4 représentent l'hydrogène alors que R2 et R3 représentent un groupe hydroxyle.2 - Composition according to claim 1, characterized in that the oligomer(s), whose elementary unit corresponds to formula (I), correspond(s) to the case where Ri and R4 represent hydrogen while R2 and R3 represent a hydroxyl group.
3 - Composition selon l'une des revendications 1 ou 2, caractérisée par le fait que les oligomères, dont le motif élémentaire a la formule (I), sont extraits d'au moins un végétal choisi dans le groupe formé par les feuilles de vigne rouge, les pépins de raisin, un mélange de feuilles de vigne rouge et de pépins de raisin, l'écorce de pin, un mélange d'écorce de pin et de pépins de raisin, les bractées de tilleul, les feuilles de noisetier, l'écorce de quinquina, les fleurs d'aubépine et la racine de rubharbe.3 - Composition according to one of claims 1 or 2, characterized in that the oligomers, whose elementary unit has formula (I), are extracted from at least one plant chosen from the group formed by vine leaves red, grape seeds, a mixture of red vine leaves and grape seeds, pine bark, a mixture of pine bark and grape seeds, linden bracts, hazel leaves, cinchona bark, hawthorn flowers and rubharb root.
4 - Composition selon l'une des revendications 1 à 3, caractérisée par le fait que la phase lipidique constitutive de la
membrane des vésicules comprend au moins un lipide choisi dans le groupe formé par :4 - Composition according to one of claims 1 to 3, characterized in that the lipid phase constituting the vesicle membrane comprises at least one lipid chosen from the group formed by:
A) les lipides non-ioniques ci-après définis : (1) les dérivés du glycérol, linéaires ou ramifiés, de formuleA) the non-ionic lipids defined below: (1) glycerol derivatives, linear or branched, of formula
-C3H5(OH)0- est représenté par les structures suivantes prises en mélange ou séparément :-C 3 H 5 (OH)0- is represented by the following structures taken as a mixture or separately:
-CH2CH0HCH20- , - CH2- CH0- , _ CH-CH20--CH 2 CH0HCH 2 0- , - CH 2 - CH0- , _ CH-CH 2 0-
CH20H CH20HCH 2 0H CH 2 0H
. q est une valeur statistique moyenne comprise entre 1 et 6 ou bien q = 1 ou 2 et alors -C3H5(OH)0- est représenté par la structure -CH2CHOH-CH2O- ;. q is an average statistical value between 1 and 6 or else q = 1 or 2 and then -C3H5(OH)0- is represented by the structure -CH2CHOH-CH2O-;
. RQ représente :. R Q represents:
(a) une chaîne aliphatique, linéaire ou ramifiée saturée ou insaturée, contenant de 12 à 30 atomes de carbone ; ou des radicaux hydrocarbonés des alcools de lanoline ; ou les restes d' alpha-diols à longue chaîne ;(a) a saturated or unsaturated aliphatic, linear or branched chain, containing 12 to 30 carbon atoms; or hydrocarbon radicals of lanolin alcohols; or remnants of long-chain alpha-diols;
(b) un reste R21CO, où R21 est un radical aliphatique, linéaire ou ramifié, en C11-C29 ; (c) un reste(b) a residue R21CO, where R21 is an aliphatic radical, linear or branched, in C11-C29; (c) a remainder
R17-[θC2H3(R23)]-R 17 -[θC 2 H 3 (R 23 )]-
où :Or :
. R17 peut prendre la signification (a) ou (b) donnée pour. R17 can take the meaning (a) or (b) given for
Ro . . -OC2H3(R23)- est représenté par les structures suivantes, prises en mélange ou séparément :
-0CH-CH2- et -0-CH2-CH-Ro. . -OC 2 H 3 (R 2 3)- is represented by the following structures, taken as a mixture or separately: -0CH-CH 2 - and -0-CH 2 -CH-
*23 R2 où R23 prend la signification (a) donnée pour RQ ; (2) les éthers de polyglycérol, linéaires ou ramifiés, comportant deux chaînes grasses ; (3) les diols à chaîne grasse ;*23 R 2 where R 2 3 takes the meaning (a) given for RQ; (2) polyglycerol ethers, linear or branched, comprising two fatty chains; (3) fatty chain diols;
(4) les alcools gras oxyéthylénés ou non, les stérols et les phytostérols oxyéthylénés ou non ;(4) oxyethylenated or non-oxyethylenated fatty alcohols, oxyethylenated or non-oxyethylenated sterols and phytosterols;
(5) les éthers et esters de polyols, oxyéthylénés ou non, l'enchaînement des oxydes d'éthylène pouvant être linéaire ou cyclique ; (5) ethers and esters of polyols, oxyethylenated or not, the sequence of ethylene oxides possibly being linear or cyclic;
(6) les glycolipides d'origine naturelle ou synthétique, les éthers et esters de mono ou polysaccharides ; (6) glycolipids of natural or synthetic origin, ethers and esters of mono or polysaccharides;
(7) les hydroxyamides représentés par la formule :(7) hydroxyamides represented by the formula:
R24- CH0H-CH-C0A _W)R 24 - CH0H-CH-C0A _W)
R5 — CONH formule (Vu) dans laquelle : - R24 désigne un radical alkyle ou alcényle en C7-C21 ;R 5 — CONH formula (Vu) in which: - R 2 4 denotes a C7-C21 alkyl or alkenyl radical;
- R5 désigne un radical hydrocarboné, saturé ou insaturé, en C7-C31 ;- R5 designates a hydrocarbon radical, saturated or unsaturated, C7-C31;
- COA désigne un groupement choisi parmi les deux groupements suivants :- COA designates a group chosen from the following two groups:
. un reste. a remainder
CON— BCON—B
"6 où :"6 where:
. B est un radical alcoyle dérivé d'aminés primaires ou secondaires, mono- ou polyhydroxylées ; et. B is an alkyl radical derived from primary or secondary, mono- or polyhydroxylated amines; And
. R£ désigne un atome d'hydrogène ou un radical méthyle, éthyle ou hydroxyéthyle ; et. R£ denotes a hydrogen atom or a methyl, ethyl or hydroxyethyl radical; And
. un reste -COOZ, où Z représente le reste d'un polyol en C3-C7.. a residue -COOZ, where Z represents the residue of a C3-C7 polyol.
(8) les céramides naturels ou de synthèse ;
(9) les dihydroxyalky lamines, les aminés grasses oxyéthylénées ; B) les lipides amphiphiles ioniques ci-après définis :(8) natural or synthetic ceramides; (9) dihydroxyalkyl amines, oxyethylenated fatty amines; B) the ionic amphiphilic lipids defined below:
(1) les lipides amphiphiles anioniques suivants :(1) the following anionic amphiphilic lipids:
• les phospholipides naturels ou modifiés par voie chimique ou enzymatique, les phospholipides de synthèse ;• natural or chemically or enzymatically modified phospholipids, synthetic phospholipids;
• les composés anioniques représentés par la formule :• anionic compounds represented by the formula:
. R3 représente un radical alkyle ou alcényle en C7-C21 . R9 représente un radical hydrocarboné, saturé ou insaturé en C7-C31, et. R3 represents a C7-C21 alkyl or alkenyl radical. R9 represents a hydrocarbon radical, saturated or unsaturated at C7-C31, and
. M représente H, Na, K, NH4 ou un ion ammonium substitué dérivé d'une aminé ;. M represents H, Na, K, NH4 or a substituted ammonium ion derived from an amine;
• les esters phosphoriques d'alcools gras sous forme d'acides ou de sels alcalins ; l'acide heptylnonylbenzène sulfonique ; le sulfate de cholestérol acide et ses sels alcalins et le phosphate de cholestérol acide et ses sels alcalins ; les lysolécithines ; les alkylsulfates ; les gangliosides ;• phosphoric esters of fatty alcohols in the form of acids or alkaline salts; heptylnonylbenzene sulfonic acid; acid cholesterol sulfate and its alkaline salts and acid cholesterol phosphate and its alkaline salts; lysolecithins; alkyl sulfates; gangliosides;
(2) les lipides amphiphiles cationiques suivants : • les composés cationiques dérivés ammonium quaternaire répondant à la formule :(2) the following cationic amphiphilic lipids: • cationic compounds derived from quaternary ammonium corresponding to the formula:
• des lipides polymérisables. 5 - Composition selon l'une des revendications 1 à 4, caractérisée par le fait que la phase lipidique constituant la membrane des vésicules contient des additifs non lipidiques.• polymerizable lipids. 5 - Composition according to one of claims 1 to 4, characterized in that the lipid phase constituting the membrane of the vesicles contains non-lipid additives.
6 - Composition selon l'une des revendications 4 ou 5, caractérisée par le fait que la phase lipidique constituant la membrane des vésicules contient de 1 à 95 % en poids de lipide(s) amphiphile(s).6 - Composition according to one of claims 4 or 5, characterized in that the lipid phase constituting the membrane of the vesicles contains from 1 to 95% by weight of amphiphilic lipid(s).
7 - Composition selon l'une des revendications 1 à 6, caractérisée par le fait que la phase aqueuse de dispersion est constituée par de l'eau ou un mélange d'eau et d'au moins un solvant miscible à l'eau. 8 - Composition selon l'une des revendications 1 à 7, caractérisée par le fait que le(s) oligomère(s) proanthocyanidinique(s) représentent) de 0,01 à 2 % en poids par rapport au poids total de la composition.7 - Composition according to one of claims 1 to 6, characterized in that the aqueous dispersion phase consists of water or a mixture of water and at least one solvent miscible with water. 8 - Composition according to one of claims 1 to 7, characterized in that the proanthocyanidin oligomer(s) represent) from 0.01 to 2% by weight relative to the total weight of the composition.
9 - Composition selon l'une des revendications 1 à 8, caractérisée par le fait que la phase lipidique constituant la membrane des vésicules représente de 0,01 % à 50 % en poids par rapport au poids total de la composition.9 - Composition according to one of claims 1 to 8, characterized in that the lipid phase constituting the membrane of the vesicles represents from 0.01% to 50% by weight relative to the total weight of the composition.
10 - Composition selon l'une des revendications 1 à 9, caractérisée par le fait que les vésicules ont des dimensions comprises entre 20 et 3 000 nm.10 - Composition according to one of claims 1 to 9, characterized in that the vesicles have dimensions between 20 and 3,000 nm.
11 - Composition selon l'une des revendications 1 à 10, caractérisée par le fait que la phase aqueuse de dispersion contient une dispersion de gouttelettes d'un liquide non-miscible à l'eau.11 - Composition according to one of claims 1 to 10, characterized in that the aqueous dispersion phase contains a dispersion of droplets of a liquid immiscible with water.
12 - Composition selon la revendication 11, caractérisée par le fait que les gouttelettes de liquide non-miscible à l'eau ont une taille comprise entre 100 et 10 000 nm.12 - Composition according to claim 11, characterized in that the droplets of liquid immiscible with water have a size between 100 and 10,000 nm.
13 - Composition selon l'une des revendications 11 ou 12, caractérisée par le fait que le liquide non-miscible à l'eau est constitué par au moins un produit choisi dans le groupe formé par :
- une huile animale ou végétale formée par des esters d'acide gras et de polyols, les triglycérides liquides, les huiles de tournesol, de maïs, de soja, de courge, de pépins de raisin, de jojoba, de sésame, de noisette, de poisson, le tricaprocaprylate de glycérol, une huile végétale ou animale de formule R19COOR20» formule dans laquelle R 9 représente le reste d'un acide gras supérieur comportant de 7 à 19 atomes de carbone et R20 représente une chaîne hydrocarbonée ramifiée contenant de 3 à 20 atomes de carbone, l'huile de Purcellin ;13 - Composition according to one of claims 11 or 12, characterized in that the liquid immiscible with water is constituted by at least one product chosen from the group formed by: - an animal or vegetable oil formed by esters of fatty acids and polyols, liquid triglycerides, sunflower, corn, soy, squash, grape seed, jojoba, sesame, hazelnut oils, of fish, glycerol tricaprocaprylate, a vegetable or animal oil of formula R19COOR20" formula in which R 9 represents the remainder of a higher fatty acid comprising from 7 to 19 carbon atoms and R20 represents a branched hydrocarbon chain containing from 3 to 20 carbon atoms, Purcellin oil;
- des huiles essentielles naturelles ou synthétiques, les huiles d'eucalyptus, de lavandin, de lavande, de vétiver, de litsea cubeba, de citron, de santal, de romarin, de camomille, de sarriette, de noix de muscade, de cannelle, d'hysope, de carvi, d'orange, de géraniol et de cade ;- natural or synthetic essential oils, oils of eucalyptus, lavandin, lavender, vetiver, litsea cubeba, lemon, sandalwood, rosemary, chamomile, savory, nutmeg, cinnamon, hyssop, caraway, orange, geraniol and cade;
- des hydrocarbures, l'hexadécane et l'huile de paraffine ; - des carbures halogènes, des fluorocarbures, des fluoroamines, des hydrocarbures fluorés, des fluoroesters et des fluoroéthers ;- hydrocarbons, hexadecane and paraffin oil; - halogenated carbides, fluorocarbons, fluoroamines, fluorinated hydrocarbons, fluoroesters and fluoroethers;
- des silicones, les polysiloxanes, les polydiméthylsiloxanes et les fluorosilicones ;- silicones, polysiloxanes, polydimethylsiloxanes and fluorosilicones;
- des esters d'acide minéral et d'un alcool ; - des éthers et des polyéthers.- esters of mineral acid and an alcohol; - ethers and polyethers.
14 - Composition selon l'une des revendications 1 à 13, caractérisée par le fait qu'elle contient au moins un adjuvant choisi dans le groupe formé par les corps gras, les solvants organiques, les silicones, les épaississants, les adoucissants, les filtres solaires UV-A, UV-B ou à bande large, les agents autobronzants, les agents antimousse, les agents hydratants, les parfums, les conservateurs, les bactéricides, les agents antipelliculaires, les agents antichutes, les agents antioxydants, les agents antiséborrhériques, les agents cicatrisants, les agents antimicrobiens, les tensioactifs, les charges, les séquestrants, les polymères anioniques, cationiques, non-ioniques, amphotères, les propulseurs, les agents alcalinisants ou acidifiants, les colorants, les agents nacrants et les pigments d'oxyde métallique.14 - Composition according to one of claims 1 to 13, characterized in that it contains at least one adjuvant chosen from the group formed by fatty substances, organic solvents, silicones, thickeners, softeners, filters UV-A, UV-B or broadband sunscreen, self-tanning agents, anti-foaming agents, moisturizing agents, perfumes, preservatives, bactericides, anti-dandruff agents, anti-hair loss agents, antioxidant agents, anti-seborrheic agents, healing agents, antimicrobial agents, surfactants, fillers, sequestrants, anionic, cationic, non-ionic, amphoteric polymers, propellants, alkalizing or acidifying agents, dyes, pearlescent agents and oxide pigments metallic.
15 - Composition selon l'une des revendications 1 à 14, utilisable pour la protection de l'épiderme humain, caractérisée par le fait qu'elle se présente sous la forme d'une crème, d'un lait, d'une pommade, d'un gel, d'un bâtonnet solide ou d'une mousse aérosol.
16 - Composition selon l'une des revendications 1 à 14, utilisable pour la protection des cheveux d'un sujet humain, caractérisée par le fait qu'elle se présente sous la forme d'un shampooing, d'une lotion, d'un gel, d'une composition à rincer à appliquer avant ou après schampooing, avant ou après coloration ou décoloration, avant, pendant ou après permanente ou défrisage, d'une lotion ou d'un gel coiffant ou traitant, d'une lotion ou d'un gel pour la mise en plis, d'une laque pour cheveux, d'une composition de permanente ou de défrisage, de coloration ou de décoloration des cheveux.15 - Composition according to one of claims 1 to 14, usable for the protection of the human epidermis, characterized in that it is in the form of a cream, a milk, an ointment, a gel, a solid stick or an aerosol foam. 16 - Composition according to one of claims 1 to 14, usable for the protection of the hair of a human subject, characterized in that it is in the form of a shampoo, a lotion, a gel, a rinse-off composition to be applied before or after shampooing, before or after coloring or bleaching, before, during or after perming or straightening, of a styling or treating lotion or gel, of a lotion or 'a gel for styling hair, a hairspray, a permanent or straightening composition, coloring or bleaching of hair.
17 - Composition selon l'une des revendications 1 à 14, utilisable comme produit de maquillage des cils, des sourcils ou de la peau, caractérisée par le fait qu'elle se présente sous forme de crème de traitement de l'épiderme, fond de teint, bâton de rouge à lèvres, fard à paupières, fard à joues, ligneur ou mascara.17 - Composition according to one of claims 1 to 14, usable as a makeup product for eyelashes, eyebrows or the skin, characterized in that it is in the form of an epidermis treatment cream, foundation complexion, lipstick stick, eye shadow, blush, liner or mascara.
18 - Composition selon l'une des revendications 1 à 14, utilisable dans une application bucco-dentaire, caractérisée par le fait qu'elle se présente sous forme de bain de bouche ou de dentifrice.18 - Composition according to one of claims 1 to 14, usable in an oral and dental application, characterized in that it is in the form of mouthwash or toothpaste.
19 - Composition selon la revendication 18, caractérisée par le fait qu'elle comprend au moins un adjuvant usuel pour les compositions à usage buccal choisi dans le groupe formé par des agents tensioactifs, des agents épaississants, des agents humectants, des agents de polissage, des agents actifs, des agents édulcorants, des agents antiplaque et des agents antitartre. 20 - Procédé de protection in vivo des muqueuses, de la peau ou des cheveux d'un sujet humain contre les radicaux libres impliqués dans des phénomènes d'oxydation, dans lesquels on applique sur le substrat à protéger au moins un oligomère proanthocyanidinique formé d'au moins un dimère, trimère ou tétramère ayant un motif élémentaire correspondant à la formule (I), caractérisé par le fait que le(s)dit(s) oligomère(s) est(sont) dissous dans une phase aqueuse encapsulée dans des vésicules délimitées par une membrane de phase lipidique constituée d'au moins un lipide amphiphile ionique et/ou d'au moins un lipide amphiphile non-ionique.
19 - Composition according to claim 18, characterized in that it comprises at least one usual adjuvant for compositions for oral use chosen from the group formed by surfactants, thickening agents, humectants, polishing agents, active agents, sweetening agents, antiplaque agents and antitartar agents. 20 - Process for in vivo protection of the mucous membranes, skin or hair of a human subject against free radicals involved in oxidation phenomena, in which at least one proanthocyanidin oligomer formed of is applied to the substrate to be protected at least one dimer, trimer or tetramer having an elementary unit corresponding to formula (I), characterized in that said oligomer(s) is(are) dissolved in an aqueous phase encapsulated in vesicles delimited by a lipid phase membrane consisting of at least one ionic amphiphilic lipid and/or at least one non-ionic amphiphilic lipid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/FR1992/000475 WO1993024106A1 (en) | 1992-05-27 | 1992-05-27 | Composition comprising a proanthocyanidin oligomer encapsulated in a liposome |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/FR1992/000475 WO1993024106A1 (en) | 1992-05-27 | 1992-05-27 | Composition comprising a proanthocyanidin oligomer encapsulated in a liposome |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1993024106A1 true WO1993024106A1 (en) | 1993-12-09 |
Family
ID=9425728
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/FR1992/000475 WO1993024106A1 (en) | 1992-05-27 | 1992-05-27 | Composition comprising a proanthocyanidin oligomer encapsulated in a liposome |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO1993024106A1 (en) |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0692243A1 (en) * | 1994-07-13 | 1996-01-17 | Caster | Depigmenting compositions containing liposomes encapsulating a concentrated plant extract rich in arbutin and OPC glycospheres |
| EP0713706A2 (en) * | 1994-11-28 | 1996-05-29 | Suntory Limited | Lipoprotein (a) lowering agent, cholesterol lowering agent and medicaments comprising these agents respectively |
| WO1996026705A1 (en) * | 1995-02-28 | 1996-09-06 | Handelman, Joseph, H. | Reduction of hair growth |
| EP0768079A1 (en) * | 1994-06-30 | 1997-04-16 | Kyowa Hakko Kogyo Co., Ltd. | Hair growth stimulant |
| EP0781544A2 (en) * | 1995-12-28 | 1997-07-02 | The Nikka Whisky Distilling Co., Ltd. | Cosmetics containing a polyphenol derived from the fruits of Rosaceae |
| EP0812592A1 (en) * | 1996-06-10 | 1997-12-17 | Kikkoman Corporation | An agent for the prevention or treatment of cataracts |
| EP0814825A1 (en) * | 1995-03-24 | 1998-01-07 | JLB, Inc., | Method of treating or preventing non-viral microbial infection |
| FR2767683A1 (en) * | 1997-08-27 | 1999-03-05 | Eric Pateroni | Hair tonic to prevent hair loss and restore color |
| WO1999044574A1 (en) * | 1998-03-06 | 1999-09-10 | Life Plus International | Toothpaste and mouth rinse compositions |
| WO1999066881A2 (en) * | 1998-06-24 | 1999-12-29 | Coty B.V. | Cosmetic preparation of active substances with high protection factor against free radicals |
| US6242005B1 (en) * | 1995-10-13 | 2001-06-05 | Charles Legrand | Absorbable prophylactic composition for protection against ionizing or non-ionizing electromagnetic waves |
| FR2810540A1 (en) * | 2000-06-21 | 2001-12-28 | C3D | Fluid aqueous composition for rejuvenation creams, foundations, lipsticks and baby creams comprises active ingredients dispersed in non-surfactant vegetable medium rich in phospholipids and glycolipids |
| EP1196162A1 (en) * | 1999-07-16 | 2002-04-17 | LG Chemical Ltd. | Procyanidin oligomers for inhibiting matrix metalloproteinases and medicine having effective composition of same |
| EP1214928A1 (en) * | 1999-08-18 | 2002-06-19 | Kyowa Hakko Kogyo Co., Ltd. | Hair growth stimulants |
| EP1232740A2 (en) * | 2001-02-16 | 2002-08-21 | Kyowa Hakko Kogyo Co., Ltd. | Hair-growing agent |
| EP1400236A1 (en) * | 2002-09-17 | 2004-03-24 | Showa Yakuhin Kako Co., Ltd | A composition for oral cavity |
| FR2873292A1 (en) * | 2004-07-23 | 2006-01-27 | Jean Noel Colombani | COMPOUNDS AND METHODS FOR CONTROLLING ALCOHOL TAKING |
| EP1621081A1 (en) * | 2003-04-30 | 2006-02-01 | Asahi Breweries, Ltd. | Material for inhibiting enamel decalcification |
| FR3114814A1 (en) | 2020-10-07 | 2022-04-08 | M&M Braun GmbH | Grape seed extract with increased positive biological efficacy, process for its production and uses thereof |
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| EP0768079A4 (en) * | 1994-06-30 | 1997-06-25 | Kyowa Hakko Kogyo Kk | Hair growth stimulant |
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| EP0781544A3 (en) * | 1995-12-28 | 1999-04-28 | The Nikka Whisky Distilling Co., Ltd. | Cosmetics containing a polyphenol derived from the fruits of Rosaceae |
| EP0781544A2 (en) * | 1995-12-28 | 1997-07-02 | The Nikka Whisky Distilling Co., Ltd. | Cosmetics containing a polyphenol derived from the fruits of Rosaceae |
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| FR2767683A1 (en) * | 1997-08-27 | 1999-03-05 | Eric Pateroni | Hair tonic to prevent hair loss and restore color |
| WO1999044574A1 (en) * | 1998-03-06 | 1999-09-10 | Life Plus International | Toothpaste and mouth rinse compositions |
| US6426080B1 (en) | 1998-06-24 | 2002-07-30 | Coty, B.V. | Cosmetic preparation of active substances with high protection factor against free radicals |
| WO1999066881A3 (en) * | 1998-06-24 | 2000-02-10 | Coty Bv | Cosmetic preparation of active substances with high protection factor against free radicals |
| WO1999066881A2 (en) * | 1998-06-24 | 1999-12-29 | Coty B.V. | Cosmetic preparation of active substances with high protection factor against free radicals |
| EP1196162A1 (en) * | 1999-07-16 | 2002-04-17 | LG Chemical Ltd. | Procyanidin oligomers for inhibiting matrix metalloproteinases and medicine having effective composition of same |
| EP1196162A4 (en) * | 1999-07-16 | 2003-06-18 | Lg Household & Health Care Ltd | Procyanidin oligomers for inhibiting matrix metalloproteinases and medicine having effective composition of same |
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| EP1400236A1 (en) * | 2002-09-17 | 2004-03-24 | Showa Yakuhin Kako Co., Ltd | A composition for oral cavity |
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