Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/67—Vitamins
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
  • A61Q19/08—Anti-ageing preparations
• • 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
  • A61K8/67—Vitamins
  • A61K8/676—Ascorbic acid, i.e. vitamin C
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/90—Block copolymers
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P17/00—Drugs for dermatological disorders
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P17/00—Drugs for dermatological disorders
  • A61P17/16—Emollients or protectives, e.g. against radiation
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
  • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening 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
  • A61Q5/08—Preparations for bleaching 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
  • A61K2800/52—Stabilizers
  • A61K2800/522—Antioxidants; Radical scavengers

Definitions

• the present invention relates to a composition
• a composition comprising at least one oxidation-sensitive hydrophilic active principle and at least one N-vinylimidazole polymer or copolymer in a physiologically acceptable medium comprising an aqueous phase, and its use in particular to prevent or treat cutaneous signs of intrinsic ageing.
• the composition is preferably a cosmetic or dermatological composition.
• ascorbic acid stimulates the synthesis of the connective tissue and in particular of collagen, strengthens the defences of the cutaneous tissue against external attacks, such as ultraviolet radiation and pollution, compensates for vitamin E deficiency of the skin, depigments the skin and has a role in combating free radicals.
• these last two properties make it an excellent candidate as cosmetic or dermatological active principle for combating ageing of the skin or for preventing ageing of the skin.
• ascorbic acid is highly sensitive to certain environmental parameters and in particular to oxidation phenomena.
• Another solution provided in the prior art consists in using a high concentration of glycols or polyols in order to reduce the solubility of oxygen in the formulation, thus protecting the ascorbic acid (WO 96/24325, EP 0 755 674, U.S. Pat. No. 5,981,578).
• the polyols can optionally be incorporated in liposomes, as disclosed in U.S. Pat. No. 6,020,367.
• these solutions exhibit the disadvantage of resulting in sticky formulations, the cosmetic quality of which is difficult to improve.
• the presence of a high concentration of these compounds can lead to phenomena of irritation.
• Ascorbic acid can also be formulated in anhydrous media, such as silicones (U.S. Pat. No. 6,194,452), which are capable of creating an anhydrous barrier around ascorbic acid.
• anhydrous media such as silicones (U.S. Pat. No. 6,194,452), which are capable of creating an anhydrous barrier around ascorbic acid.
• composition employable in particular in the cosmetics field, in which a hydrophilic active principle which is unstable in an oxidizing medium is stabilized, which is comfortable on application, which does not lead to any skin irritation after application and which is compatible with the constraints of an industrial implementation of its manufacturing process.
• One object of the present invention is to provide a composition comprising an oxidation-sensitive active principle for example selected from the group consisting of ascorbic acid and its derivatives, which exhibits good cosmetic properties, both with regard to touch and with regard to tolerance, the preservation of which over time does not require specific precautions, and which retains the activity of the said active principle in the prevention and/or the treatment of cutaneous signs of intrinsic ageing.
• an oxidation-sensitive active principle for example selected from the group consisting of ascorbic acid and its derivatives, which exhibits good cosmetic properties, both with regard to touch and with regard to tolerance, the preservation of which over time does not require specific precautions, and which retains the activity of the said active principle in the prevention and/or the treatment of cutaneous signs of intrinsic ageing.
• N-vinylimidazole/N-vinylcaprolactam/N-vinylpyrrolidone copolymers are disclosed in U.S. Pat. No. 6,191,188. They are used in the manufacture of hair-strengthening compositions.
• One embodiment of the present invention is therefore the preferably cosmetic and/or dermatological use, for preventing and/or treating cutaneous signs of intrinsic ageing, of a composition
• a composition comprising, in a physiologically acceptable medium comprising an aqueous phase, at least one oxidation-sensitive hydrophilic active principle preferably selected from the group consisting of ascorbic acid and its derivatives and at least one non-crosslinked N-vinylimidazole polymer or copolymer, the active principle and the polymer or copolymer both being in the aqueous phase.
• the copolymer is preferably present in an amount sufficient to stabilize the said oxidation-sensitive hydrophilic active principle, and the composition is preferably applied to those areas of the skin in need of such prevention and/or treatment.
• Another embodiment of the invention is the use of a combination composed of at least one oxidation-sensitive hydrophilic active principle preferably selected from the group consisting of ascorbic acid and its derivatives and of at least one non-crosslinked N-vinylimidazole polymer or copolymer in the aqueous phase-of a cosmetic composition as agent for preventing and/or treating cutaneous signs of intrinsic ageing.
• at least one oxidation-sensitive hydrophilic active principle preferably selected from the group consisting of ascorbic acid and its derivatives and of at least one non-crosslinked N-vinylimidazole polymer or copolymer in the aqueous phase-of a cosmetic composition as agent for preventing and/or treating cutaneous signs of intrinsic ageing.
• the term “intrinsic ageing” is understood to mean the ageing which occurs because of modifications due to endogenous factors, in contrast to ageing caused by exogenous factors, such as photoageing.
• the changes in the skin which occur are then revealed for example by a thinning of the dermis, a loss of elasticity, a deepening of the imperfections and the appearance of fine lines.
• hydrophilic active principle is understood to mean a compound having a solubility in water of at least 0.25% at ambient temperature (25° C.).
• the term “oxidation-sensitive hydrophilic active principle” is understood to mean any active principle of natural or synthetic origin capable of undergoing decomposition by an oxidation mechanism. This oxidation phenomenon can have several causes, in particular the presence of oxygen, of light or of metal ions, a high temperature or certain pH conditions.
• ascorbic acid and its derivatives such as salts and esters thereof, particularly the 5,6-di-O-dimethylsilyascorbate (sold by Exsymol under the reference PRO-AA), the potassium salt of dl- ⁇ -tocopheryl dl-ascorbyl phosphate (sold by Senju Pharmaceutical under the reference SEPIVITAL EPC), magnesium ascorbyl phosphate or sodium ascorbyl phosphate (sold by Roche under the reference Stay-C 50).
• the principle is preferably present in an amount sufficient to prevent and/or treat cutaneous signs of ageing, such as 0.1, 1, 5 and 25 g per 100 g. Any principle useful for this purpose and meeting the requirements of hydrophilicity and oxidation sensitivity may be used.
• the oxidation-sensitive hydrophilic active principle is ascorbic acid.
• non-crosslinked N-vinylimidazole polymer or copolymer is understood to mean any polymer comprising N-vinylimidazole units and not comprising a crosslinking agent.
• Copolymers suitable for the implementation of the invention are copolymers combining N-vinylimidazole with N-vinylpyrrolidone and/or N-vinylcaprolactam subunits.
• the copolymer has a molar fraction of N-vinylimidazole units of between 0.1 and 1, more preferably between 0.4 and 0.9, inclusive.
• the molar ratio of the N-vinylimidazole unit equivalent to the oxidation-sensitive hydrophilic active principle varies between 0.004 and 16 and preferably between 0.01 and 1, inclusive.
• Use will preferably be made of an N-vinylimidazole/N-vinylpyrrolidone copolymer.
• the weight-average molar mass of the N-vinylimidazole polymers will advantageously be between 1 000 and 1 ⁇ 107 and preferably between 5 000 and 5 ⁇ 106.
• Use may be made, to this end, of the vinylpyrrolidone/vinylimidazole (50/50) copolymer having a weight-average molar mass of 1 200 000 sold under the reference LUVITEC VPI 55K72W by BASF or the vinylpyrrolidone/vinylimidazole (50/50) copolymer having a weight-average molar mass of 10 000 sold under the reference LUVITEC VPI 55K18P by BASF.
• the at least one polymer or copolymer is preferably present in the composition according to the invention in an amount sufficient to produce the desired effect, that is to say in an amount sufficient to stabilize the oxidation-sensitive hydrophilic active principle.
• the copolymer is present at a concentration of between 0.1 and 5% by weight with respect to the total weight of the aqueous phase and more particularly at a concentration of between 0.1 and 2% by weight with respect to the total weight of the aqueous phase, inclusive.
• the amount stabilizes the active principle by slowing or stopping decomposition at 45° C. for two months.
• compositions used according to the invention are preferably intended for topical application to the skin and/or its superficial body growths and therefore comprise a physiologically acceptable medium, that is to say a medium compatible with cutaneous tissues, such as the skin, scalp, eyelashes, eyebrows, hair, nails and mucous membranes.
• This physiologically acceptable medium comprises an aqueous phase and optionally a physiologically acceptable organic solvent chosen, for example, from lower alcohols comprising from 1 to 8 carbon atoms and in particular from 1 to 6 carbon atoms, such as ethanol, isopropanol, propanol or butanol; polyethylene glycols having from 6 to 80 ethylene oxide units; or polyols, such as propylene glycol, isoprene glycol, butylene glycol, glycerol or sorbitol.
• a physiologically acceptable organic solvent chosen, for example, from lower alcohols comprising from 1 to 8 carbon atoms and in particular from 1 to 6 carbon atoms, such as ethanol, isopropanol, propanol or butanol; polyethylene glycols having from 6 to 80 ethylene oxide units; or polyols, such as propylene glycol, isoprene glycol, butylene glycol, glycerol or sorbitol.
• the physiologically acceptable medium is an aqueous medium, it generally preferably has a pH which is compatible with the skin, preferably ranging from 3 to 9 and better still from 3.5 to 7.5.
• compositions according to the invention can be provided in any form, including any pharmaceutical dosage form used for topical application and in particular in the form of aqueous or aqueous/alcoholic solutions, of oil-in-water (O/W) or water-in-oil (W/O) or multiple (triple: W/O/W or O/W/O) emulsions, of aqueous gels or of dispersions of a fatty phase in an aqueous phase using spherules, it being possible for these spherules to be polymeric nanoparticles, such as nanospheres and nanocapsules, or lipid vesicles of ionic and/or nonionic type (liposomes, niosomes or oleosomes). These compositions are prepared according to the usual methods.
• compositions used according to the invention can be more or less fluid and can have the appearance of a white or coloured cream, of an ointment, of a milk, of a lotion, of a serum, of a paste or of a foam. They can optionally be applied to the skin in the form of an aerosol. They can also be provided in a solid form, for example in the form of a stick.
• composition used according to the invention comprises an oily phase
• the latter preferably comprises at least one oil. It can additionally comprise other fatty substances.
• oils which can be used in the composition of the invention of, for example:
• hydrocarbonaceous oils of animal origin such as perhydrosqualene
• hydrocarbonaceous oils of vegetable origin such as liquid triglycerides of fatty acids comprising from 4 to 10 carbon atoms, such as triglycerides of heptanoic acid or octanoic acid, or alternatively, for example, sunflower, maize, soybean, gourd, grape seed, sesame, hazelnut, apricot, macadamia, arara, castor or avocado oils, triglycerides of caprylic/capric acids, such as those sold by Stéarineries Dubois or those sold under the names Miglyol 810, 812 and 818 by Dynamit Nobel, jojoba oil, or karite butter oil;
• esters and ethers in particular of fatty acids, such as the oils of formulae R1COOR2 and R1OR2 in which R1 represents the residue of a fatty acid comprising from 8 to 29 carbon atoms and R2 represents a branched or unbranched hydrocarbonaceous chain comprising from 3 to 30 carbon atoms, such as, for example, purcellin oil, isononyl isononanoate, isopropyl myristate, 2-ethylhexyl palmitate, 2-octyldodecyl stearate, 2-octyldodecyl erucate or isostearyl isostearate; hydroxylated esters, such as isostearyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate, triisocetyl citrate or heptanoates, octano
• linear or branched hydrocarbons of mineral or synthetic origin such as volatile or nonvolatile liquid paraffins and their derivatives, liquid petrolatum, polydecenes or hydrogenated polyisobutene, such as sesam oil;
• fatty alcohols having from 8 to 26 carbon atoms such as cetyl alcohol, stearyl alcohol and their mixture (cetearyl alcohol), octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol, oleyl alcohol or linoleyl alcohol;
• silicone oils such as volatile or nonvolatile polymethylsiloxanes (PDMS) comprising a linear or cyclic silicone chain which are liquid or pasty at ambient temperature, in particular cyclopolydimethylsiloxanes (cyclomethicones), such as cyclohexasiloxane; polydimethylsiloxanes comprising pendent alkyl, alkoxy or phenyl groups or alkyl, alkoxy or phenyl groups at the end of the silicone chain, which groups have from 2 to 24 carbon atoms; or phenylated silicones, such as phenyl trimethicones, phenyl dimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyl dimethicones, diphenylmethyldiphenyltrisiloxanes, (2-phenylethyl)trimethylsiloxysilicates and polymethylphenylsiloxanes;
• PDMS volatile or nonvol
• hydrocarbonaceous oil is understood to mean, in the list of the oils mentioned above, any oil predominantly comprising carbon and hydrogen atoms and optionally ester, ether, fluorinated, carboxylic acid and/or alcohol groups.
• the other fatty substances which can be present in the oily phase are, for example, fatty acids comprising from 8 to 30 carbon atoms, such as stearic acid, lauric acid, palmitic acid and oleic acid; waxes, such as lanolin, beeswax, camauba or candelilla wax, paraffin or lignite waxes or microcrystalline waxes, ceresin or ozokerite, or synthetic waxes, such as polyethylene waxes or Fischer-Tropsch waxes; silicone resins, such as trifluoromethyl C1-4 alkyl dimethicone and trifluoropropyl dimethicone; and silicone elastomers, such as the products sold under the names “KSG” by Shin-Etsu, under the names “Trefil”, “BY29” or “EPSX” by Dow Corning or under the names “Gransil” by Grant Industries.
• fatty acids comprising from 8 to 30 carbon atoms, such as stearic acid
• fatty substances can be chosen in a way varied by a person skilled in the art in order to prepare a composition having the desired properties, for example of consistency or of texture, without undue hardship.
• the composition according to the invention is a water-in-oil (W/O) or oil-in-water (O/W) emulsion.
• W/O water-in-oil
• O/W oil-in-water
• the proportion of the oily phase in the emulsion can preferably range from 5 to 80% by weight and preferably from 5 to 50% by weight with respect to the total weight of the composition.
• the emulsions generally comprise at least one emulsifier selected from the group consisting of amphoteric, anionic, cationic or nonionic emulsifiers, used alone or as a mixture, and optionally a coemulsifier.
• the emulsifiers are appropriately chosen according to the emulsion to be obtained (W/O or O/W).
• the emulsifier and the coemulsifier are generally present in the composition in a proportion ranging from 0.3 to 30% by weight and preferably from 0.5 to 20% by weight with respect to the total weight of the composition.
• W/O emulsions for example, as emulsifiers, of dimethicone copolyols, such as the mixture of cyclomethicone and of dimethicone copolyol sold under the name “DC 5225 C” by Dow Coming, and alkyl dimethicone copolyols, such as the laurylmethicone copolyol sold under the name “Dow Corning 5200 Formulation Aid” by Dow Coming and the cetyl dimethicone copolyol sold under the name Abil EM 90R by Goldschmidt.
• dimethicone copolyols such as the mixture of cyclomethicone and of dimethicone copolyol sold under the name “DC 5225 C” by Dow Coming
• alkyl dimethicone copolyols such as the laurylmethicone copolyol sold under the name “Dow Corning 5200 Formulation Aid” by Dow Coming and the cetyl dime
• Use may also be made, as surfactant of W/O emulsions, of a crosslinked solid organopolysiloxane elastomer comprising at least one oxyalkylenated group, such as those obtained according to the procedure of Examples 3, 4 and 8 of the document U.S. Pat. No. 5,412,004 and the examples of the document U.S. Pat. No. 5,811,487, in particular the product of Example 3 (synthetic example) of patent U.S. Pat. No. 5,412,004, and such as that sold under the reference KSG 21 by Shin Etsu.
• Use may also be made, as emulsifier, of a polyolefin-derived oligomer or polymer comprising a succinic ending; the latter is preferably a polyolefin comprising an esterified or amidated succinic ending or a salt of such a polyolefin and in particular polyisobutylene comprising an esterified or amidated succinic ending such as the products sold under the names L5603 and L2721 and OS131769 by Lubrizol.
• O/W emulsions for example, as emulsifiers, of nonionic emulsifiers, such as esters of fatty acids and of glycerol which are oxyalkylenated (more particularly polyoxyethylenated); esters of fatty acids and of sorbitan which are oxyalkylenated; esters of fatty acids which are oxyalkylenated (oxyethylenated and/or oxypropylenated); ethers of fatty alcohols which are oxyethylenated (oxyethylenated and/or oxypropylenated); sugar esters, such as sucrose stearate; and their mixtures, such as the mixture of glyceryl stearate and of PEG-40 stearate.
• nonionic emulsifiers such as esters of fatty acids and of glycerol which are oxyalkylenated (more particularly polyoxyethylenated); esters of fatty acids
• composition of the invention can also comprise adjuvants known in the cosmetics or dermatological field, such as hydrophilic or lipophilic gelling agents, preservatives, solvents, fragrances, fillers, UV screening agents, bactericides, odour absorbers, colouring materials, plant extracts or salts.
• adjuvants known in the cosmetics or dermatological field, such as hydrophilic or lipophilic gelling agents, preservatives, solvents, fragrances, fillers, UV screening agents, bactericides, odour absorbers, colouring materials, plant extracts or salts.
• the amounts of these various adjuvants are those conventionally used in the field under consideration, for example from 0.01 to 20% of the total weight of the composition.
• These adjuvants depending on their nature, can be introduced into the fatty phase, into the aqueous phase and/or into the lipid spherules.
• fillers which can be used in the composition of the invention, for example, of pigments, silica powder; talc; particles of polyamide and in particular those sold under the name Orgasol by Atochem; polyethylene powders; microspheres based on acrylic copolymers, such as those made of ethylene glycol dimethacrylate/lauryl methacrylate copolymer which are sold by Dow Corning under the name Polytrap; expanded powders, such as hollow microspheres and in particular the microspheres sold under the name Expancel by Kemanord Plast or under the name Micropearl F 80 ED by Matsumoto; silicone resin microbeads, such as those sold under the name Tospearl by Toshiba Silicone; and their mixtures.
• These fillers can be present in amounts ranging from 0 to 20% by weight and preferably from 1 to 10% by weight with respect to the total weight of the composition.
• compositions in accordance with the invention can additionally comprise at least one organic photoprotective agent and/or at least one inorganic photoprotective agent which is active in the UV-A and/or UV-B regions (absorbers), and which are soluble in water or in fats or else are insoluble in the cosmetic solvents commonly used.
• at least one organic photoprotective agent and/or at least one inorganic photoprotective agent which is active in the UV-A and/or UV-B regions (absorbers), and which are soluble in water or in fats or else are insoluble in the cosmetic solvents commonly used.
• organic photoprotective agents are chosen in particular from anthranilates; cinnamic derivatives; dibenzoylmethane derivatives; salicylic derivatives; camphor derivatives; triazine derivatives, such as those disclosed in patent applications U.S. Pat. No.
• PABA p-aminobenzoic acid
• salicylic derivatives in particular homosalate (sold under the name “Eusolex HMS” by Rona/EM Industries), ethylhexyl salicylate (sold under the name “Neo Heliopan OS” by Haarmann and Reimer), dipropylene glycol salicylate (sold under the name “Dipsal” by Scher), or TEA salicylate (sold under the name “Neo Heliopan TS” by Haarmann and Reimer),
• dibenzoylmethane derivatives in particular butyl methoxydibenzoylmethane (sold in particular under the trade name “Parsol 1789” by Hoffmann-LaRoche), or isopropyl dibenzoylmethane,
• cinnamic derivatives in particular ethylhexyl methoxycinnamate (sold in particular under the trade name “Parsol MCX” by Hoffmann-LaRoche), isopropyl methoxycinnamate, isoamyl methoxycinnamate (sold under the trade name “Neo Heliopan E 1000” by Haarmann and Reimer), cinoxate, DEA methoxycinnamate, diisopropyl methyl cinnamate, or glyceryl ethylhexanoate dimethoxycinnamate,
• ⁇ , ⁇ -diphenylacrylate derivatives in particular octocrylene (sold in particular under the trade name “Uvinul N539” by BASF) or etocrylene (sold in particular under the trade name “Uvinul N35” by BASF),
• benzophenone in particular benzophenone-1 (sold under the trade name “Uvinul 400” by BASF), benzophenone-2 (sold under the trade name “Uvinul D50” by BASF), benzophenone-3 or oxybenzone (sold under the trade name “Uvinul M40” by BASF), benzophenone-4 (sold under the trade name “Uvinul MS40” by BASF), benzophenone-5, benzophenone-6 (sold under the trade name “Helisorb 11” by Norquay), benzophenone-8 (sold under the trade name “Spectra-Sorb UV-24” by American Cyanamid), benzophenone-9 (sold under the trade name “Uvinul DS-49” by BASF), benzophenone-12, or n-hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate,
• benzylidene camphor derivatives in particular 3-benzylidene camphor (manufactured under the name “Mexoryl SD” by Chimex), 4-methylbenzylidene camphor (sold under the name “Eusolex 6300” by Merck), benzylidene camphor sulphonic acid (manufactured under the name “Mexoryl SL” by Chimex), camphor benzalkonium methosulphate (manufactured under the name “Mexoryl SO” by Chimex), terephthalylidene dicamphor sulphonic acid (manufactured under the name “Mexoryl SX” by Chimex), or polyacrylamidomethyl benzylidene camphor (manufactured under the name “Mesoryl SW” by Chimex),
• benzimidazole derivatives in particular phenylbenzimidazole sulphonic acid (sold in particular under the trade name “Eusolex 232” by Merck), or disodium phenyl dibenzimidazole tetrasulphonate (sold under the trade name “Neo Heliopan AP” by Haarmann and Reimer),
• triazine derivatives in particular anisotriazine (sold under the trade name “Tinosorb S” by Ciba Specialty Chemicals), ethylhexyl triazone (sold in particular under the trade name “Uvinul T150” by BASF), diethylhexyl butamido triazone (sold under the trade name “Uvasorb HEB” by Sigma 3V) or 2,4,6-tris(diisobutyl 4′-amino-benzalmalonate)-s-triazine,
• benzotriazole derivatives in particular drometrizole trisiloxane (sold under the name “Silatrizole” by Rhodia Chimie) or methylene bisbenzotriazolyl tetramethylbutylphenol (sold in the solid form under the trade name “Mixxim BB/100” by Fairmount Chemical or in the micronized form in aqueous dispersion under the trade name “Tinosorb M” by Ciba Specialty Chemicals),
• anthranilic derivatives in particular menthyl anthranilate (sold under the trade name “Neo Heliopan MA” by Haarmann and Reimer),
• imidazoline derivatives in particular ethylhexyl dimethoxybenzylidene dioxoimidazoline propionate,
• benzalmalonate derivatives in particular polyorganosiloxane comprising benzalmalonate functional groups (sold under the trade name “Parsol SLX” by Hoffmann-LaRoche),
• the organic photoprotective agents which are more particularly preferred are selected from the group consisting of ethylhexyl salicylate, ethylhexyl methoxycinnamate, octocrylene, phenylbenzimidazole sulphonic acid, benzophenone-3, benzophenone-4, benzophenone-5, 4-methylbenzylidene camphor, terephthalylidene dicamphor sulphonic acid, disodium phenyl dibenzimidazole tetrasulphonate, 2,4,6-tris(diisobutyl 4′-aminobenzalmalonate)-s-triazine, anisotriazine, ethylhexyl triazone, diethylhexyl butamido triazone, methylene bisbenzotriazolyl tetramethylbutylphenol, drometrizole trisiloxane, 1,1′-dicarbox
• the inorganic photoprotective agents may be selected from the group consisting of pigments or alternatively nanopigments (mean size of the primary particles: generally between 5 nm and 100 nm, preferably between 10 nm and 50 nm) formed from coated or uncoated metal oxides, such as, for example, titanium oxide (amorphous or crystalline in the rutile and/or anatase form), iron oxide, zinc oxide, zirconium oxide or cerium oxide nanopigments, which are all UV photoprotective agents well known per se.
• Conventional coating agents are, furthermore, alumina and/or aluminium stearate.
• Such nanopigments formed from coated or uncoated metal oxides are disclosed in particular in Patent Applications EP 518 772 and EP 518 773.
• the photoprotective agents are generally preferably present in the compositions according to the invention in proportions ranging from 0.1 to 20% by weight with respect to the total weight of the composition and preferably ranging from 0.2 to 15% by weight with respect to the total weight of the composition.
• the composition can additionally (that is, in addition to the principle described above) comprise at least one other active principle which stimulates dermal macromolecules or which prevents their decomposition and/or one agent which stimulates the proliferation of fibroblasts or keratinocytes and/or the differentiation of keratinocytes.
• Examples include active principles which stimulate dermal macromolecules or which prevent their decomposition, those which act:
• elastin such as the extract of Saccharomyces cerevisiae sold by LSN under the trade name Cytovitin®; and the extract of the alga Macrocystis pyrifera sold by Secma under the trade name Kelpadelie®;
• glycosaminoglycans such as the product of fermentation of milk by Lactobacillus vulgaris sold by Brooks under the trade name Biomin yogourth®; the extract of the brown alga Padina pavonica sold by Alban Müller under the trade name HSP3®; and the extract of Saccharomyces cerevisiae available in particular from Silab under the trade name Firmalift® or from LSN under the trade name Cytovitin®;
• fibronectin such as the extract of Salina zooplankton sold by Seporga under the trade name GP4G®;
• yeast extract available in particular from Alban Müller under the trade name Drieline®; and the palmitoyl pentapeptide sold by Sederma under the trade name Matrixil®;
• MMP metalloproteinases
• Mention may be made of: retinoids and derivatives; oligopeptides and lipopeptides, lipoamino acids; the malt extract sold by Coletica under the trade name Collalift®; extracts of blueberry or of rosemary; lycopene; or isoflavones, their derivatives or the plant extracts comprising them, in particular extracts of soybean (sold, for example, by Ichimaru Pharcos under the trade name Flavosterone SB®), of red clover, of flax, of kakkon or of sage;
• serine proteases such as leukocyte elastase or cathepsin G. Mention may be made of: the peptide extract of Leguminosae ( Pisum sativum ) seeds sold by LSN under the trade name Parelastyl®; heparinoids; and pseudodipeptides.
• the agents which stimulate the proliferation of fibroblasts which can be used in the composition according to the invention can, for example, be selected from the group consisting of plant proteins or polypeptides, extracts, in particular of soybean (for example, a soybean extract sold by LSN under the name Eleseryl SH-VEG 8® or sold by Silab under the trade name Raffermine®); and plant hormones, such as gibberellins and cytokinins.
• soybean for example, a soybean extract sold by LSN under the name Eleseryl SH-VEG 8® or sold by Silab under the trade name Raffermine®
• plant hormones such as gibberellins and cytokinins.
• the agents which stimulate the proliferation of keratinocytes which can be used in the composition according to the invention may comprise in particular retinoids, such as retinol and its esters, including retinyl palmitate; phloroglucinol ; the extracts of walnut meal sold by Gattefossé; and the extracts of Solanum tuberosum sold by Sederma.
• retinoids such as retinol and its esters, including retinyl palmitate; phloroglucinol ; the extracts of walnut meal sold by Gattefossé; and the extracts of Solanum tuberosum sold by Sederma.
• the agents which stimulate the differentiation of keratinocytes include for example inorganic materials, such as calcium; the extract of lupin sold by Silab under the trade name Photogenieventine®; sodium ⁇ -sitosteryl sulphate, sold by Seporga under the trade name Phytocohésine®; and the extract of maize sold by Solabia under the trade name Phytovityl®.
• the composition according to the invention can be applied to the skin or mucous membranes. It can thus be used in a cosmetic treatment process for the purpose of preventing and/or treating cutaneous signs of intrinsic ageing, comprising the application of the composition according to the invention to the skin or mucous membranes, particularly skin or membranes especially subject to such ageing and its signs, and more particularly such skin and membranes visible in normal activity.
• composition according to the invention can be used for the manufacture of a dermatological preparation comprising an aqueous phase which is intended to prevent and/or treat cutaneous signs of intrinsic ageing.
• Polymer 1 Vinylpyrrolidone/vinylimidazole (50/50) copolymer sold under the reference Luvitec VPI 55K72W of BASF (Weight-average molecular mass 1.2 ⁇ 10 6 ).
• Polymer 2 Vinylpyrrolidone/vinylimidazole (50/50) copolymer sold under the reference Luvitec VPI 55K8P of BASF (Weight-average molecular mass 10 000).
• Polymer 3 Polyvinylpyrrolidone sold under the reference Kollidon 12PF of BASF (Weight-average molecular mass 3 000).
• the concentration of ascorbic acid is determined by the HPLC technique (LaChrom Merck system).
• the analytical conditions are as follows:
• polymers mentioned are hydrophilic, it will be sufficient to add them to an aqueous ascorbic acid solution to stabilize the ascorbic acid.
• the present example describes the effects of the addition of a combination according to the invention, comprising ascorbic acid and a polymer or copolymer according to the invention, on reconstructed skin by observation with a microscope of a skin section with immunohistochimical labelling of the proteins of tenascin and collagen VII.
• the inoculation of the keratinocytes is carried out in a proportion of 50 000 cells per ring with a diameter of 1.5 cm.
• the keratinocytes used originate from the same donor and are at passage 1 during the inoculation of the dermal equivalents;
• the duration of the immersion phase is 7 days
• the duration of the emergence phase is 7 days.
• the final change in medium of the immersion phase is carried out in the presence of the combination of ascorbic acid and of vinylpyrrolidone/vinylimidazole.
• the culture is subsequently mounted on a grid for the emergence phase (7 days) and, during this phase, all changes in medium (every 2 days) are carried out in the presence of the above combination.
• the samples are taken and frozen in liquid nitrogen.
• the blocks are produced from Tissue Teck.
• Collagen of type VII is detected by immunohistochemistry on frozen sections with a thickness of 5 ⁇ m.
• the conventional indirect immunofluorescence technique is carried out with an anticollagen VII monoclonal antibody (LH7.2, Chemicon International Inc., USA) and a fluorescein-coupled conjugate (FITC-conjugated Rabbit anti mouse immunoglobulins, DAKO, Denmark).
• the protocol used is that described in point 3.a. above, except that, in this case, the tenascin is detected with an antitenascin monoclonal antibody (TN2, Chemicon) and a fluorescein-coupled conjugate (FITC-conjugated Rabbit anti mouse immunoglobulins, DAKO, Denmark).
• TN2 antitenascin monoclonal antibody
• FITC-conjugated Rabbit anti mouse immunoglobulins DAKO, Denmark.
• composition is prepared in a way conventional to a person skilled in the art.
• This cream which is soft and fresh on application makes it possible to combat wrinkles and fine lines and has a good degree of stabilization for the ascorbic acid.
• compositions comprising, preferably in a physiologically acceptable medium comprising an aqueous phase, at least one oxidation-sensitive hydrophilic active principle for example selected from the group consisting of ascorbic acid and its derivatives and at least one non-crosslinked N-vinylimidazole polymer or copolymer, the active principle and the polymer or copolymer both being present in the aqueous phase.
• a physiologically acceptable medium comprising an aqueous phase
• at least one oxidation-sensitive hydrophilic active principle for example selected from the group consisting of ascorbic acid and its derivatives and at least one non-crosslinked N-vinylimidazole polymer or copolymer, the active principle and the polymer or copolymer both being present in the aqueous phase.
• a combination comprising at least one oxidation-sensitive hydrophilic active principle selected from the group consisting of ascorbic acid and its derivatives and of at least one non-crosslinked N-vinylimidazole polymer or copolymer in the aqueous phase of a cosmetic composition as an agent for preventing and/or treating cutaneous signs of intrinsic ageing.
• at least one oxidation-sensitive hydrophilic active principle selected from the group consisting of ascorbic acid and its derivatives and of at least one non-crosslinked N-vinylimidazole polymer or copolymer for the preparation of a dermatological composition comprising an aqueous phase which is intended to prevent and/or treat cutaneous signs of intrinsic ageing.
• a cosmetic treatment process intended to prevent and/or treat cutaneous signs of intrinsic ageing, comprising the application, to the skin or mucous membranes, of a composition comprising, preferably in a physiologically acceptable medium comprising an aqueous phase, at least one oxidation-sensitive hydrophilic active principle selected from the group consisting of ascorbic acid and its derivatives and at least one non-crosslinked N-vinylimidazole polymer or copolymer, the active principle and the polymer or copolymer both being in the aqueous phase.
• a method for preventing and/or treating cutaneous signs of intrinsic ageing comprising applying a composition comprising a physiologically acceptable medium comprising an aqueous phase, at least one oxidation-sensitive hydrophilic active principle selected from the group consisting of ascorbic acid and its derivatives, and at least one non-crosslinked N-vinylimidazole polymer or copolymer to a cutaneous tissue, the active principle and the polymer or copolymer both being present in the aqueous phase of the composition.
• French patent application 0115375 is incorporated herein by reference, as are all references, texts, documents, patents, applications, standards, etc. mentioned above. Where a numerical range is stated all values therebetween are included as if specifically written out.

Landscapes

• Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Veterinary Medicine (AREA)
• Public Health (AREA)
• General Health & Medical Sciences (AREA)
• Animal Behavior & Ethology (AREA)
• Birds (AREA)
• Dermatology (AREA)
• Epidemiology (AREA)
• General Chemical & Material Sciences (AREA)
• Pharmacology & Pharmacy (AREA)
• Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Chemical & Material Sciences (AREA)
• Bioinformatics & Cheminformatics (AREA)
• Gerontology & Geriatric Medicine (AREA)
• Medicinal Chemistry (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Toxicology (AREA)
• Cosmetics (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
• Medicinal Preparation (AREA)

Applications Claiming Priority (3)

Publications (1)

Family

ID=8869872

Family Applications (5)

Family Applications After (4)

Country Status (11)

Cited By (6)

Families Citing this family (44)

Citations (20)

Family Cites Families (22)

• 2001
  • 2001-11-28 FR FR0115375A patent/FR2832630B1/fr not_active Expired - Fee Related
• 2002
  • 2002-11-12 EP EP02292812A patent/EP1316306A1/de not_active Withdrawn
  • 2002-11-12 EP EP02292809A patent/EP1316303A1/de not_active Withdrawn
  • 2002-11-12 EP EP02292811A patent/EP1316305A1/de not_active Withdrawn
  • 2002-11-12 EP EP02292808A patent/EP1316302B1/de not_active Expired - Lifetime
  • 2002-11-12 ES ES02292808T patent/ES2292705T3/es not_active Expired - Lifetime
  • 2002-11-12 DE DE60222223T patent/DE60222223T2/de not_active Expired - Lifetime
  • 2002-11-12 AT AT02292808T patent/ATE372109T1/de not_active IP Right Cessation
  • 2002-11-12 EP EP02292810A patent/EP1316304A1/de not_active Withdrawn
  • 2002-11-27 TW TW091134443A patent/TW200408411A/zh unknown
  • 2002-11-27 US US10/304,862 patent/US20030125378A1/en not_active Abandoned
  • 2002-11-27 JP JP2002344603A patent/JP3606858B2/ja not_active Expired - Fee Related
  • 2002-11-27 US US10/304,861 patent/US20030124075A1/en not_active Abandoned
  • 2002-11-27 JP JP2002344601A patent/JP3606856B2/ja not_active Expired - Fee Related
  • 2002-11-27 US US10/305,115 patent/US20030133889A1/en not_active Abandoned
  • 2002-11-27 TW TW091134446A patent/TW200303760A/zh unknown
  • 2002-11-27 JP JP2002344600A patent/JP3655276B2/ja not_active Expired - Fee Related
  • 2002-11-27 JP JP2002344604A patent/JP3606859B2/ja not_active Expired - Fee Related
  • 2002-11-27 US US10/304,860 patent/US7560493B2/en not_active Expired - Fee Related
  • 2002-11-27 BR BR0205119-2A patent/BR0205119A/pt not_active IP Right Cessation
  • 2002-11-27 BR BR0205120-6A patent/BR0205120A/pt not_active IP Right Cessation
  • 2002-11-27 TW TW091134445A patent/TW200303764A/zh unknown
  • 2002-11-27 JP JP2002344602A patent/JP3606857B2/ja not_active Expired - Fee Related
  • 2002-11-27 US US10/305,114 patent/US20030124161A1/en not_active Abandoned
  • 2002-11-27 TW TW091134442A patent/TW200304831A/zh unknown
  • 2002-11-27 TW TW091134444A patent/TW200303763A/zh unknown
  • 2002-11-28 KR KR1020020074584A patent/KR20030043763A/ko active IP Right Grant
  • 2002-11-28 BR BR0205122-2A patent/BR0205122A/pt not_active IP Right Cessation
  • 2002-11-28 KR KR10-2002-0074587A patent/KR100514465B1/ko not_active IP Right Cessation
  • 2002-11-28 CN CN02152785A patent/CN1421197A/zh active Pending
  • 2002-11-28 CN CNB021527830A patent/CN1200687C/zh not_active Expired - Fee Related
  • 2002-11-28 CN CNB021527822A patent/CN1228039C/zh not_active Expired - Fee Related
  • 2002-11-28 CN CNB021527849A patent/CN1230148C/zh not_active Expired - Fee Related
  • 2002-11-28 KR KR10-2002-0074586A patent/KR100514464B1/ko not_active IP Right Cessation
  • 2002-11-28 BR BR0205152-4A patent/BR0205152A/pt not_active IP Right Cessation
  • 2002-11-28 KR KR10-2002-0074588A patent/KR100524240B1/ko not_active IP Right Cessation
  • 2002-11-28 KR KR10-2002-0074585A patent/KR100514463B1/ko not_active IP Right Cessation
  • 2002-11-28 BR BR0205135-4A patent/BR0205135A/pt not_active IP Right Cessation
  • 2002-11-28 CN CNB021527814A patent/CN1187035C/zh not_active Expired - Fee Related

Patent Citations (20)

Also Published As

Similar Documents

Legal Events