WO2009098139A1 - Composition cosmétique contenant un dérivé de dibenzoylméthane et un dérivé d'ester d'acide n-acylamino neutre particulier ; procédé de photostabilisation du dérivé de dibenzoylméthane - Google Patents
Composition cosmétique contenant un dérivé de dibenzoylméthane et un dérivé d'ester d'acide n-acylamino neutre particulier ; procédé de photostabilisation du dérivé de dibenzoylméthane Download PDFInfo
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- 229940074347 totarol Drugs 0.000 description 1
- GYDJEQRTZSCIOI-LJGSYFOKSA-N tranexamic acid Chemical compound NC[C@H]1CC[C@H](C(O)=O)CC1 GYDJEQRTZSCIOI-LJGSYFOKSA-N 0.000 description 1
- 229960000401 tranexamic acid Drugs 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- ZRVDANDJSTYELM-UHFFFAOYSA-N trans-totarol Natural products C1CC2C(C)(C)CCCC2(C)C2=C1C(C(C)C)=C(O)C=C2 ZRVDANDJSTYELM-UHFFFAOYSA-N 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 229960001325 triclocarban Drugs 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- HTJNEBVCZXHBNJ-XCTPRCOBSA-H trimagnesium;(2r)-2-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxy-2h-furan-5-one;diphosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.OC[C@H](O)[C@H]1OC(=O)C(O)=C1O HTJNEBVCZXHBNJ-XCTPRCOBSA-H 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- SMYKBXMWXCZOLU-UHFFFAOYSA-N tris-decyl benzene-1,2,4-tricarboxylate Chemical compound CCCCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCCCC)C(C(=O)OCCCCCCCCCC)=C1 SMYKBXMWXCZOLU-UHFFFAOYSA-N 0.000 description 1
- OHOTVSOGTVKXEL-UHFFFAOYSA-K trisodium;2-[bis(carboxylatomethyl)amino]propanoate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C(C)N(CC([O-])=O)CC([O-])=O OHOTVSOGTVKXEL-UHFFFAOYSA-K 0.000 description 1
- 150000003648 triterpenes Chemical class 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 229960000821 visnadine Drugs 0.000 description 1
- 235000009492 vitamin B5 Nutrition 0.000 description 1
- 239000011675 vitamin B5 Substances 0.000 description 1
- 235000001892 vitamin D2 Nutrition 0.000 description 1
- 239000011653 vitamin D2 Substances 0.000 description 1
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 1
- 235000005282 vitamin D3 Nutrition 0.000 description 1
- 239000011647 vitamin D3 Substances 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 229940021056 vitamin d3 Drugs 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000008307 w/o/w-emulsion Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 235000020097 white wine Nutrition 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
- 229940118846 witch hazel Drugs 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- FJHBOVDFOQMZRV-XQIHNALSSA-N xanthophyll Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C=C(C)C(O)CC2(C)C FJHBOVDFOQMZRV-XQIHNALSSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 229940022860 xylitan Drugs 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
- 235000010930 zeaxanthin Nutrition 0.000 description 1
- 239000001775 zeaxanthin Substances 0.000 description 1
- 229940043269 zeaxanthin Drugs 0.000 description 1
- 229940118827 zinc phenolsulfonate Drugs 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- BOVNWDGXGNVNQD-UHFFFAOYSA-L zinc;2-hydroxybenzenesulfonate Chemical compound [Zn+2].OC1=CC=CC=C1S([O-])(=O)=O.OC1=CC=CC=C1S([O-])(=O)=O BOVNWDGXGNVNQD-UHFFFAOYSA-L 0.000 description 1
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical class [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 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
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
Definitions
- the present invention relates to a cosmetic composition containing a combination of at least one screening agent of the dibenzoylmethane derivative type and at least one particular neutral N-acylamino acid ester derivative of formula (I), the definition of which will be given hereinbelow.
- the invention also relates to a process for radiation- photostabilizing at least one screening agent of the dibenzoylmethane derivative type with an effective amount of at least one particular neutral N-acylamino acid ester derivative of formula (I), the definition of which will be given hereinbelow.
- the present invention also relates to the use of at least one particular neutral N-acylamino acid ester derivative of formula (I) in a composition comprising, in a cosmetically acceptable support, at least one dibenzoylmethane derivative, for the purpose of improving the efficacy of the said composition with respect to UV-A rays.
- UV-B rays light rays with wavelengths more particularly between 280 and 320 nm, known as UV-B rays, cause skin burns and erythema which can harm the development of a natural tan.
- UV-A rays with wavelengths between 320 and 400 nm, which cause tanning of the skin, are liable to induce adverse changes therein, in particular in the case of sensitive skin or skin that is continually exposed to solar radiation.
- UV-A rays cause in particular a loss of elasticity of the skin and the appearance of wrinkles leading to premature ageing of the skin. They promote triggering of the erythemal reaction or amplify this reaction in certain individuals and may even be the cause of phototoxic or photoallergic reactions. Thus, for aesthetic and cosmetic reasons, for instance conservation of the skin' s natural elasticity, an increasingly large number of people wish to control the effect of UV-A rays on their skin. It is thus desirable also to screen out UV- A radiation.
- antisun compositions comprising organic screening agents that are active in the UV-A range and in the UV-B range are generally used.
- the majority of these screening agents are liposoluble .
- one particularly advantageous family of UV-A screening agents currently consists of dibenzoylmethane derivatives, and in particular 4-tert- butyl-4 ' -methoxydibenzoylmethane, which have high intrinsic absorbing power.
- dibenzoylmethane derivatives which are products that are now well known per se as screening agents that are active in the UV-A range, are described in particular in French patent applications FR-A-2 326 405 and FR-A-2 440 933, and also in European patent application EP-A-O 114 607; 4- tert-butyl-4' -methoxydibenzoylmethane is moreover currently sold under the trade name Parsol 1789 by the company DSM Nutritional Products.
- dibenzoylmethane derivatives are products that are relatively sensitive to ultraviolet radiation (especially UV-A), i.e., more specifically, they have an annoying tendency to be degraded more or less quickly under the action of this UV.
- UV-A ultraviolet radiation
- this substantial lack of photochemical stability of dibenzoylmethane derivatives towards ultraviolet radiation, to which they are by nature intended to be subjected does not make it possible to ensure constant protection during prolonged exposure to the sun, and so the user must make repeated applications at regular and close time intervals in order to obtain effective protection of the skin against UV rays.
- amide compounds have a photostabilizing effect on dibenzoylmethane derivatives and more particularly N, N-disubstituted amide oils, for instance the compound N, N-diethyl-3- methylbenzamide, having the structure:
- Photostabilization of dibenzoylmethane derivatives towards UV-radiation with amide compounds thus constitutes, at the present time, a problem that has still not been solved entirely satisfactorily.
- composition comprising, in a cosmetically acceptable support, at least one UV-screening system, characterized in that it comprises:
- Another subject of the invention also concerns a process for improving the chemical stability towards UV radiation of at least one dibenzoylmethane derivative, which consists in combining the said dibenzoylmethane derivative with an effective amount of at least one neutral N-acylamino acid ester derivative such as those cited above.
- a subject of the present invention is also the use of at least one neutral N-acylamino acid ester derivative such as those cited above, in a composition comprising, in a cosmetically acceptable support, at least one dibenzoylmethane derivative, for the purpose of improving the efficacy of the said composition with respect to UV-A rays.
- cosmetically acceptable means compatible with the skin and/or its integuments, which has a pleasant colour, odour and feel, and which does not cause any unacceptable discomfort (stinging, tautness or redness) liable to put the consumer off using this composition .
- an effective amount means an amount that is sufficient to obtain an appreciable and significant improvement in the photostability of the dibenzoylmethane derivative (s) in the cosmetic composition.
- This minimum amount of particular neutral N-acylamino acid ester derivative which may vary according to the nature of the support adopted for the composition, may be determined without any difficulty by means of a standard test for measuring photostability, such as that given in the examples hereinbelow.
- a compound that is particularly preferred will be compound (c) , which has the nomenclature 2-hexyldecyl N-myristoyl-N-methylaminopropionate and which is sold under the trade name Amiter MA-HD by the company Nihon Emulsion Co. Ltd.
- neutral N-acylamino acid ester derivative compounds in accordance with the present invention may be prepared according to the process described in the literature, and more particularly in the following references :
- R 1 and R 2 denote a linear or branched Ci-C 2 O alkyl radical
- R 3 represents a hydrogen atom or a linear or branched C 1 -C 4 alkyl radical
- R 4 represents a linear or branched Ci-C 30 alkyl radical, is prepared by reacting an amine of formula (III) with the acrylic derivative of formula (II) .
- Compound (IV) is then acylated by reaction with an acid chloride of formula (V), and compound (I) is obtained by distillation of the crude reaction product.
- the particular neutral N-acylamino acid ester derivatives are preferably present in the composition according to the invention in a content ranging from 0.1% to 40% by weight and preferably ranging from 0.1% to 30% by weight relative to the total weight of the composition .
- dibenzoylmethane derivatives that may especially be mentioned, in a non-limiting manner, are:
- 4-isopropyldibenzoylmethane will be used in particular, which is sold under the name Eusolex 8020 by the company Merck, and corresponds to the following formula :
- the dibenzoylmethane derivative (s) may be present in the compositions in accordance with the invention in contents preferably ranging from 0.01% to 10% by weight and more preferably from 0.1% to 6% by weight relative to the total weight of the composition.
- compositions in accordance with the invention may also comprise other additional UVA-active and/or UVB- active organic or mineral UV-screening agents that are water-soluble or liposoluble or even insoluble in the cosmetic solvents commonly used.
- the additional organic screening agents are chosen especially from anthranilates; cinnamic derivatives; salicylic derivatives; camphor derivatives; benzophenone derivatives; ⁇ , ⁇ -diphenylacrylate derivatives; triazine derivatives; benzotriazole derivatives; benzalmalonate derivatives, especially those mentioned in patent US 5 624 663; benzimidazole derivatives; imidazolines; bis-benzazolyl derivatives as described in patents EP 669 323 and US 2 463 264; p- aminobenzoic acid (PABA) derivatives; methylenebis- (hydroxyphenylbenzotriazole) derivatives as described in patent applications US 5 237 071, US 5 166 355, GB 2 303 549, DE 197 26 184 and EP 893 119; benzoxazole derivatives as described in patent applications EP 0 832 642, EP 1 027 883, EP 1 300 137 and DE 101 62 844; screening polymers and screening silicones such as those described
- organic UV-screening agents mention may be made of those denoted hereinbelow under their INCI name : para-Aminobenzoic acid derivatives:
- Ethylhexyl dimethyl PABA sold in particular under the name Escalol 507 by ISP,
- PEG-25 PABA sold under the name Uvinul P25 by BASF.
- Neo Isoamyl methoxycinnamate sold under the trade name Neo
- Etocrylene sold in particular under the trade name
- Benzophenone- 12 n-hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate sold under the trade name Uvinul A+, or in the form of a mixture with octyl methoxycinnamate under the trade name Uvinul A+B by BASF.
- Phenylbenzimidazolesulfonic acid sold in particular under the trade name Eusolex 232 by Merck, Disodium phenyl dibenzimidazole tetrasulfonate sold under the trade name Neo Heliopan AP by Haarmann and Reimer .
- Neoethyl anthranilate sold under the trade name Neo
- Imidazoline derivatives Ethylhexyldimethoxybenzylidenedioxoimidazoline propionate.
- Polyorganosiloxane containing benzalmalonate functions for instance Polysilicone-15, sold under the trade name Parsol SLX by Hoffmann LaRoche
- the preferred additional organic photoprotective agents are chosen from:
- the additional mineral screening agents are chosen from coated or uncoated metal oxide pigments in which the mean size of the primary particles is preferentially between 5 nm and 100 nm (preferably between 10 nm and 50 nm) , for instance titanium oxide (amorphous or crystallized in rutile and/or anatase form) , iron oxide, zinc oxide, zirconium oxide or cerium oxide pigments, which are all UV-photoprotective agents that are well known per se.
- the pigments may be coated or uncoated.
- coated pigments are pigments that have undergone one or more surface treatments of chemical, electronic, mechanochemical and/or mechanical nature with compounds as described, for example, in Cosmetics & Toiletries,
- silicones are organosilicon polymers or oligomers of linear or cyclic, branched or crosslinked structure, of variable molecular weight, obtained by polymerization and/or polycondensation of suitably functionalized silanes, and consist essentially of a repetition of main units in which the silicon atoms are linked together via oxygen atoms (siloxane bond), optionally substituted hydrocarbon-based radicals being directly attached via a carbon atom to the said silicon atoms .
- sicones also includes the silanes required for their preparation, in particular alkyl silanes.
- the silicones used for coating the nanopigments that are suitable for the present invention are preferably chosen from the group containing alkyl silanes, polydialkylsiloxanes and polyalkylhydrogenosiloxanes . Even more preferentially, the silicones are chosen from the group containing octyltrimethylsilane, polydimeth- ylsiloxanes and polymethylhydrogenosiloxanes .
- the metal oxide pigments may have been treated with other surface agents, in particular with cerium oxide, alumina, silica, aluminium compounds or silicon compounds, or mixtures thereof.
- coated pigments are more particularly titanium oxides that have been coated:
- silica such as the product Sunveil from the company Ikeda and the product Eusolex T-AVO from the company Merck
- silica and iron oxide such as the product Sunveil F from the company Ikeda
- silica and alumina such as the products
- alumina such as the products Tipaque TTO-55 (B) and Tipaque TTO-55 (A) from the company Ishihara and UVT 14/4 from the company Kemira, with alumina and aluminium stearate, such as the product Microtitanium Dioxide MT 100 TV, MT 100 TX, MT 100 Z and MT-Ol from the company Tayca, and the products Solaveil CT-IO W, Solaveil CT 100 and Solaveil
- a silicone such as the products Microtitanium Dioxide MT 600 SAS, Microtitanium Dioxide MT 500 SAS or Microtitanium Dioxide MT 100 SAS from the company Tayca, with silica, alumina and aluminium stearate and treated with a silicone, such as the product STT-30-DS from the company Titan Kogyo, - with silica and treated with a silicone, such as the product UV-Titan X 195 from the company Kemira, or the product SMT-100 WRS from the company Tayca,
- titanium oxide pigments treated with a silicone are preferably T1O2 treated with octyltrimethylsilane and for which the mean size of the elementary particles is between 25 and 40 nm, such as the product sold under the trade name T 805 by the company Degussa Silices, Ti ⁇ 2 treated with a polydimethylsiloxane and for which the mean size of the elementary particles is 21 nm, such as the product sold under the trade name 70250 Cardre UF Ti ⁇ 2SI3 by the company Cardre, anatase/rutile Ti ⁇ 2 treated with a polydimethylhydrogenosiloxane and for which the mean size of the elementary particles is 25 nm, such as the product sold under the trade name Microtitanium Dioxide USP Grade Hydrophobic by the company Color Techniques.
- the uncoated titanium oxide pigments are sold, for example, by the company Tayca under the trade names Microtitanium Dioxide MT 500 B or Microtitanium Dioxide MT 600 B, by the company Degussa under the name P 25, by the company Wackher under the name Transparent titanium oxide PW, by the company Miyoshi Kasei under the name UFTR, by the company Tomen under the name ITS and by the company Tioxide under the name Tioveil AQ.
- the uncoated zinc oxide pigments are, for example: - those sold under the name Z-Cote by the company Sunsmart .
- coated zinc oxide pigments are, for example:
- the uncoated cerium oxide pigments are sold under the name Colloidal Cerium Oxide by the company Rhone-Poulenc.
- coated iron oxide pigments are sold, for example, by the company BASF under the name Transparent Iron Oxide .
- metal oxides especially of titanium dioxide and of cerium dioxide, including the silica-coated equal-weight mixture of titanium dioxide and of cerium dioxide, sold by the company Ikeda under the name Sunveil A, and also the alumina, silica and silicone-coated mixture of titanium dioxide and of zinc dioxide, such as the product M 261 sold by the company Kemira, or the alumina, silica and glycerol-coated mixture of titanium dioxide and
- the additional UV-screening agents are generally present in the compositions according to the invention in proportions ranging from 0.01% to 20% by weight relative to the total weight of the composition, and preferably ranging from 0.1% to 10% by weight relative to the total weight of the composition.
- aqueous compositions in accordance with the present invention may also comprise standard cosmetic adjuvants chosen especially from fatty substances, organic solvents, ionic or nonionic, hydrophilic or lipophilic thickeners, softeners, humectants, opacifiers, stabilizers, emollients, silicones, antifoams, fragrances, preserving agents, anionic, cationic, nonionic, zwitterionic or amphoteric surfactants, active agents, fillers, polymers, propellants, acidifying or basifying agents or any other ingredient usually used in cosmetics and/or dermatology.
- standard cosmetic adjuvants chosen especially from fatty substances, organic solvents, ionic or nonionic, hydrophilic or lipophilic thickeners, softeners, humectants, opacifiers, stabilizers, emollients, silicones, antifoams, fragrances, preserving agents, anionic, cationic, nonionic, zwitterionic or
- the fatty substances may consist of an oil or a wax other than the apolar waxes as defined above, or mixtures thereof.
- oil means a compound that is liquid at room temperature.
- wax means a compound that is solid or substantially solid at room temperature and whose melting point is generally greater than 35°C.
- Oils that may be mentioned include mineral oils (paraffin) ; plant oils (sweet almond oil, macadamia oil, grapeseed oil or jojoba oil); synthetic oils, for instance perhydrosqualene, fatty alcohols, fatty amides
- fatty acids or fatty esters for instance the C12-C15 alkyl benzoate sold under the trade name Finsolv TN or
- Witconol TN by the company Witco, 2-ethylphenyl benzoate, for instance the commercial product sold under the name X-Tend 226® by the company ISP, octyl palmitate, isopropyl lanolate and triglycerides, including capric/caprylic acid triglycerides, and dicaprylyl carbonate sold under the name Cetiol CC by the company Cognis, oxyethylenated or oxypropylenated fatty esters and ethers; silicone oils (cyclomethicone and polydimethylsiloxanes, or PDMS) or fluoro oils, polyalkylenes, and trialkyl trimellitates such as tridecyl trimellitate .
- silicone oils cyclomethicone and polydimethylsiloxanes, or PDMS
- fluoro oils polyalkylenes
- trialkyl trimellitates such as tridecyl trimellitate .
- Waxy compounds that may be mentioned include carnauba wax, beeswax, hydrogenated castor oil, polyethylene waxes and polymethylene waxes, for instance the product sold under the name Cirebelle 303 by the company Sasol.
- organic solvents that may be mentioned are lower alcohols and polyols.
- These polyols may be chosen from glycols and glycol ethers, for instance ethylene glycol, propylene glycol, butylene glycol, dipropylene glycol or diethylene glycol.
- Hydrophilic thickeners that may be mentioned include carboxyvinyl polymers such as the Carbopol products (carbomers) and the Pemulen products (acrylate/C10-C30- alkylacrylate copolymer) ; polyacrylamides, for instance the crosslinked copolymers sold under the names Sepigel 305 (CTFA name: polyacrylamide/C13-14 isoparaffin/ Laureth 7) or Simulgel 600 (CTFA name: acryl- amide/sodium acryloyldimethyltaurate copolymer/isohexa- decane/polysorbate 80) by the company SEPPIC; 2-acrylamido-2-methylpropanesulfonic acid polymers and copolymers, which are optionally crosslinked and/or neutralized, for instance the poly (2-acrylamido-2- methylpropanesulfonic acid) sold by the company Hoechst under the trade name Hostacerin AMPS (CTFA name: ammonium polyacryloyldi
- Lipophilic thickeners that may be mentioned include synthetic polymers such as poly(Cio-C3o alkyl acrylates) sold under the name Intelimer IPA 13-1 and Intelimer IPA 13-6 by the company Landec, or modified clays such as hectorite and its derivatives, for instance the products sold under the name Bentone.
- compositions according to the invention may be prepared according to techniques that are well known to those skilled in the art. They may be in particular in the form of a simple or complex emulsion (O/W, W/O, 0/W/O or W/O/W emulsion) such as a cream, a milk or a cream-gel; in the form of an aqueous gel; in the form of a lotion. They may optionally be packaged as an aerosol and may be in the form of a mousse or a spray.
- compositions according to the invention are preferably in the form of an oil-in-water or water-in- oil emulsion.
- the emulsions generally contain at least one emulsifier chosen from amphoteric, anionic, cationic and nonionic emulsifiers, which are used alone or as a mixture.
- the emulsifiers are appropriately chosen according to the emulsion to be obtained (W/O or O/W) .
- the emulsions may also contain stabilizers of other types, for instance fillers, gelling polymers or thickeners.
- emulsifying surfactants that may be used for the preparation of the W/0 emulsions
- examples that may be mentioned include sorbitan, glycerol or sugar alkyl esters or ethers; silicone surfactants, for instance dimethicone copolyols, such as the mixture of cyclomethicone and of dimethicone copolyol, sold under the name DC 5225 C by the company Dow Corning, and alkyldimethicone copolyols such as laurylmethicone copolyol sold under the name Dow Corning 5200 Formulation Aid by the company Dow Corning; cetyl- dimethicone copolyol, such as the product sold under the name Abil EM 9OR by the company Goldschmidt, and the mixture of cetyldimethicone copolyol, of poly- glyceryl isostearate (4 mol) and of hexyl laurate, sold under the name Abil WE 09 by the company
- Polyol alkyl esters that may especially be mentioned include polyethylene glycol esters, for instance PEG-30 dipolyhydroxystearate, such as the product sold under the name Arlacel P135 by the company ICI.
- Glycerol and/or sorbitan esters that may especially be mentioned include, for example, polyglyceryl isostearate, such as the product sold under the name Isolan GI 34 by the company Goldschmidt, sorbitan isostearate, such as the product sold under the name Arlacel 987 by the company ICI, sorbitan glyceryl isostearate, such as the product sold under the name Arlacel 986 by the company ICI, and mixtures thereof.
- emulsifiers examples include nonionic emulsifiers such as oxyalkylenated (more particularly polyoxyethylenated) fatty acid esters of glycerol; oxyalkylenated fatty acid esters of sorbitan; oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty acid esters, for instance the mixture PEG-100 stearate/glyceryl stearate sold, for example, by the company ICI under the name Arlacel 165; oxyalkylenated (oxyethylenated and/or oxypropylenated) fatty alkyl ethers; sugar esters, for instance sucrose stearate; fatty alkyl ethers of sugars, especially polyalkylglucosides (APG) such as decylglucoside and laurylglucoside sold, for example, by the company Hen
- APG polyalkylglucosides
- the mixture of the alkylpolyglucoside as defined above with the corresponding fatty alcohol may be in the form of a self-emulsifying composition as described, for example, in document WO-A-92/06778.
- emulsion stabilizers that will be used more particularly are isophthalic acid or sulfo- isophthalic acid polymers, and in particular phthal- ate/sulfoisophthalate/glycol copolymers, for example the diethylene glycol/phthalate/isophthalate/1, 4-cyclo- hexanedimethanol copolymer (INCI name: Polyester-5) sold under the name Eastman AQ Polymer (AQ35S, AQ38S, AQ55S and AQ48 Ultra) by the company Eastman Chemical.
- isophthalic acid or sulfo- isophthalic acid polymers and in particular phthal- ate/sulfoisophthalate/glycol copolymers, for example the diethylene glycol/phthalate/isophthalate/1, 4-cyclo- hexanedimethanol copolymer (INCI name: Polyester-5) sold under the name Eastman AQ Polymer (AQ35S, AQ38S, AQ55S and AQ48
- the aqueous phase of this emulsion may comprise a nonionic vesicular dispersion prepared according to known processes (Bangham, Standish and Watkins, J. MoI. Biol. 13, 238 (1965), FR 2 315 991 and FR 2 416 008) .
- compositions according to the invention find their application in a large number of treatments, especially cosmetic treatments, of the skin, the lips and the hair, including the scalp, especially for protecting and/or caring for the skin, the lips and/or the hair, and/or for making up the skin and/or the lips.
- compositions according to the invention as defined above for the manufacture of cosmetic products for treating the skin, the lips, the nails, the hair, the eyelashes, the eyebrows and/or the scalp, especially care products, antisun products and makeup products .
- the cosmetic compositions according to the invention may be used, for example, as makeup products.
- compositions according to the invention may be used, for example, as care products and/or antisun protection products for the face and/or the body, of liquid to semi-liquid consistency, such as milks, more or less rich creams, cream-gels and pastes. They may optionally be conditioned in aerosol form and may be in the form of a mousse or a spray.
- compositions according to the invention in the form of vaporizable fluid lotions in accordance with the invention are applied to the skin or the hair in the form of fine particles by means of pressurization devices.
- the devices in accordance with the invention are well known to those skilled in the art and comprise non-aerosol pumps or "atomizers", aerosol containers comprising a propellant and also aerosol pumps using compressed air as propellant. These devices are described in patents US 4 077 441 and US 4 850 517 (which form an integral part of the content of the description) .
- compositions conditioned in aerosol form in accordance with the invention generally contain conventional propellants, for instance hydrofluoro compounds, dichlorodifluoromethane, difluoroethane, dimethyl ether, isobutane, n-butane, propane or trichlorofluoromethane . They are preferably present in amounts ranging from 15% to 50% by weight relative to the total weight of the composition.
- compositions according to the invention may also comprise additional cosmetic or dermatological active agents .
- the additional active agents may be chosen especially from moisturizers, desquamating agents, agents for improving the barrier function, depigmenting agents, antioxidants, dermo-decontracting agents, anti- glycation agents, agents for stimulating the synthesis of dermal and/or epidermal macromolecules and/or for preventing their degradation, agents for stimulating fibroblast or keratinocyte proliferation and/or keratinocyte differentiation, agents for promoting the maturation of the horny envelope, NO-synthase inhibitors, peripheral benzodiazepine receptor (PBR) antagonists, agents for increasing the activity of the sebaceous glands, agents for stimulating the energy metabolism of cells, tensioning agents, lipo- restructuring agents, slimming agents, agents for promoting the cutaneous capillary circulation, calmatives and/or anti-irritants, sebo-regulators or anti-seborrhoeic agents, astringents, cicatrizing agents, anti-inflammatory agents and antiacne agents.
- a person skilled in the art will select the said active agent (s) as a function of the effect desired on the skin, the hair, the eyelashes, the eyebrows and the nails.
- moisturizers For caring for and/or making up aged skin, he will preferably choose at least one active agent chosen from moisturizers, desquamating agents, agents for improving the barrier function, depigmenting agents, antioxidants, dermo-decontracting agents, anti-glycation agents, agents for stimulating the synthesis of dermal and/or epidermal macromolecules and/or for preventing their degradation, agents for stimulating fibroblast or keratinocyte proliferation and/or keratinocyte differentiation, agents for promoting the maturation of the horny envelope, NO-synthase inhibitors, peripheral benzodiazepine receptor (PBR) antagonists, agents for increasing the activity of the sebaceous glands, agents for stimulating the energy metabolism of cells, and agents for promoting the cutaneous microcirculation for the area around the eyes.
- active agent chosen from moisturizers, desquamating agents, agents for improving the barrier function, depigmenting agents, antioxidants, dermo-decontracting agents, anti-glycation agents, agents for stimulating
- composition may also comprise at least one ingredient such as fillers with a soft-focus effect or agents for promoting the natural coloration of the skin, intended for complementing the biological effects of these active agents or for providing an immediate visual anti-ageing effect.
- ingredient such as fillers with a soft-focus effect or agents for promoting the natural coloration of the skin, intended for complementing the biological effects of these active agents or for providing an immediate visual anti-ageing effect.
- a person skilled in the art will preferably choose at least one active agent chosen from desquamating agents, sebo- regulating agents or anti-seborrhoeic agents, and astringents .
- composition may also comprise at least one additional ingredient for complementing the biological effect of these active agents or for providing an immediate visual effect; mention may be made especially of matting agents, fillers with a soft-focus effect, fluorescers, agents for promoting the naturally pinkish coloration of the skin, and abrasive fillers or exfoliants.
- Moisturizers or humectants that may especially be mentioned include glycerol and derivatives thereof, urea and derivatives thereof, especially Hydrovance® sold by National Starch, lactic acid, hyaluronic acid, AHAs, BHAs, sodium pidolate, xylitol, serine, sodium lactate, ectoin and derivatives thereof, chitosan and derivatives thereof, collagen, plankton, an extract of Imperata cylindra sold under the name Moist 24® by the company Sederma, acrylic acid homopolymers, for instance Lipidure-HM® from NOF Corporation, beta-glucan from Mibelle-AG-Biochemistry; a mixture of passionflower oil, apricot oil, corn oil and rice bran oil sold by Nestle under the name NutraLipids®; a C- glycoside derivative such as those described in patent application WO 02/051 828 and in particular C- ⁇ -D- xylopyranoside-2-hydroxypropan
- the moisturizer that will preferably be used is chosen from urea and derivatives thereof, especially Hydrovance® sold by National Starch, hyaluronic acid, AHAs, BHAs, acrylic acid homopolymers, for instance Lipidure-HM® from NOF Corporation, beta-glucan from Mibelle-AG-Biochemistry; a mixture of passionflower oil, apricot oil, corn oil and rice bran oil sold by Nestle under the name NutraLipids®; a C-glycoside derivative such as those described in patent application WO 02/051 828 and in particular C- ⁇ -D- xylopyranoside-2-hydroxypropane in the form of a solution containing 30% by weight of active material in a water/propylene glycol mixture (60/40% by weight) such as the product sold by Chimex under the trade name Mexoryl SBB®; an oil of musk rose sold by Nestle; an oil of the microalga Prophyridium cruentum enriched with zinc, sold by Vinci
- treating agent means any compound capable of acting:
- ⁇ -hydroxy acids BHA
- salicylic acid and derivatives thereof including 5-n-octanoylsalicylic acid, also known as capryloyl salicylic acid as the INCI name
- AHA ⁇ -hydroxy acids
- AHA such as glycolic acid, citric acid, lactic acid, tartaric acid, malic acid or mandelic acid
- gentisic acid and derivatives thereof oligofucoses; cinnamic acid; Saphora japonica extract; resveratrol, and certain jasmonic acid derivatives
- ⁇ -hydroxy acids AHA
- AHA ⁇ -hydroxy acids
- aminosulfonic compounds and in particular 4- (2- hydroxyethyl) piperazine-1-propanesulfonic acid (HEPES); 2-oxothiazolidine-4-carboxylic acid (procysteine) derivatives; derivatives of ⁇ -amino acids of glycine type (as described in EP-O 852 949, and also sodium methyl glycine diacetate sold by BASF under the trade name Trilon M); honey; O-octanoyl-6-D-maltose and N- acetylglucosamine .
- HPES 4- (2- hydroxyethyl) piperazine-1-propanesulfonic acid
- procysteine 2-oxothiazolidine-4-carboxylic acid
- derivatives of ⁇ -amino acids of glycine type as described in EP-O 852 949, and also sodium methyl glycine diacetate sold by BASF under the trade name Trilon M
- honey O
- desquamating agents that may be used in the composition according to the invention, mention may be made of: oligofructoses, EDTA and derivatives thereof, laminaria extracts, o-linoleyl-6D-glucose, (3-hydroxy-
- Preferred desquamating agents include ⁇ -hydroxy acids such as 5-n-octanoyl salicylic acid; urea; glycolic acid, citric acid, lactic acid, tartaric acid, malic acid or mandelic acid; 4- (2- hydroxyethyl) piperazine-1-propanesulfonic acid (HEPES); extract of Saphora japonica; honey; N-acetyl glucosamine; sodium methyl glycine diacetate, and mixtures thereof.
- ⁇ -hydroxy acids such as 5-n-octanoyl salicylic acid; urea; glycolic acid, citric acid, lactic acid, tartaric acid, malic acid or mandelic acid; 4- (2- hydroxyethyl) piperazine-1-propanesulfonic acid (HEPES); extract of Saphora japonica; honey; N-acetyl glucosamine; sodium methyl glycine diacetate, and mixtures thereof.
- a desquamating agent chosen from 5-n-octanoyl salicylic acid; urea; 4- (2- hydroxyethyl) piperazine-1-propanesulfonic acid (HEPES); extract of Saphora japonica; honey; N-acetyl glucosamine; sodium methyl glycine diacetate, and mixtures thereof, will be used in the compositions of the invention.
- arginine an extract of Thermus thermophilus such as Venuceane® from Sederma, an extract of the rhizome of wild yam (Dioscorea villosa) such as Actigen Y® from Active Organics, plankton extracts, for instance Omega Plankton® from Secma, yeast extracts, for instance Relipidium® from Coletica, a chestnut extract such as Recoverine® from Silab, a cedar bud extract such as Gatuline Zen® from Gattefosse, sphingosines, for instance salicyloyl sphingosine sold under the name Phytosphingosine® SLC by the company Degussa, a mixture of xylitol, polyxylityl glycoside and xylitan, for instance Aquaxyl® from SEPPIC, extracts of Solanacea plants, for instance Lipidessence® from Coletica, omega-3 unsaturated
- ceramides or derivatives thereof in particular ceramides of type 2 (for instance N-oleoyldihydrosphingosine) , of type 3 (for instance stearoyl-4-hydroxysphinganine, as the INCI name) and of type 5 (for instance N-2- hydroxypalmitoyldihydrosphingosine, having the INCI name: hydroxypalmitoyl sphinganine) , sphingoid-based compounds, glycosphingolipids, phospholipids, cholesterol and derivatives thereof, phytosterols, essential fatty acids, diacylglycerol, 4-chromanone and chromone derivatives, petroleum jelly, lanolin, shea butter, cocoa butter, lanolin and PCA salts.
- type 2 for instance N-oleoyldihydrosphingosine
- type 3 for instance stearoyl-4-hydroxysphinganine, as the INCI name
- type 5 for instance N-2- hydroxypalmito
- an extract of Thermus thermophilics an extract of wild yam rhizome (Dioscorea villosa) , a yeast extract, a chestnut extract, a cedar bud extract, arginine, ceramides especially of type 3 and 5; and mixtures thereof .
- serine or arginine or a mixture thereof, will be used.
- Depigmenting agents that may especially be mentioned include vitamin C and derivatives thereof and especially vitamin CG, CP and 3-0 ethyl vitamin C, alpha and beta arbutin, ferulic acid, lucinol and derivatives thereof, kojic acid, resorcinol and derivatives thereof, tranexamic acid and derivatives thereof, gentisic acid, homogentisate, methyl gentisate or homogentisate, dioic acid, calcium D-pantheteine sulfonate, lipoic acid, ellagic acid, vitamin B3, linoleic acid and derivatives thereof, ceramides and homologues thereof, plant derivatives, for instance camomile, bearberry, the aloe family (vera, ferox, bardensis), mulberry or skullcap; a kiwi fruit
- tocopherol and esters thereof in particular tocopheryl acetate; ascorbic acid and derivatives thereof, in particular magnesium ascorbyl phosphate and ascorbyl glucoside; ferulic acid; serine; ellagic acid, polyphenols, tannins, tannic acid, epigallocatechins and natural extracts containing them, anthocyans, rosemary extracts, olive leaf extracts, for instance those from the company Silab, green tea extracts, resveratrol and derivatives thereof, ergothioneine, N-acetylcysteine, an extract of the brown alga Pelvetia caniculata, for instance Pelvetiane® from Secma, chlorogenic acid, biotin, chelating agents, such as BHT and BHA, N, N' -bis (3, 4, 5- trimethoxybenzyl) ethylenediamine and salts thereof; idebenone, plant extracts, for instance Pronalen Bioprotect TM from the
- anti-ageing agents include DHEA and derivatives thereof, boswellic acid, rosemary extracts, carotenoids ( ⁇ -carotene, zeaxanthin and lutein), cysteic acid, copper derivatives and jasmonic acid.
- Preferred antioxidants that will especially be used include ferulic acid; serine; phloretin, an extract of pomegranate, biotin, chelating agents such as BHT, BHA, N, N' -bis (3, 4, 5-trimethoxybenzyl) ethylenediamine and salts thereof; caprylyl glycol, phloretin, TotarolTM, a jasmine extract such as the product sold by Silab under the name Helisun®; hesperitin laurate such as Flavagrum PEG® from the company Engelhard Lyon; an extract of Paeonia suffruticosa root, such as the product sold by the company Ichimaru Pharcos under the name Botanpi Liquid B®.
- Examples that may be mentioned include manganese gluconate and other salts, adenosine, alverine citrate and salts thereof, lysine, an extract of Iris pallida, a hexapeptide (Argeriline R from Lipotec) or sapogenins, for instance wild yam and the carbonyl amines described in patent application EP 1 484 052.
- sapogenins examples include those described in patent application WO 02/47650, in particular wild yam, the diosgenin extracted especially from Dioscorea opposita or any extract naturally containing or containing after treatment one or more sapogenins (wild yam rhizome, agave leaf, which contains hecogenin and tigogenin, extracts of Liliacea plants and more particularly yucca or smilax containing smilagenin and sarsapogenin, or sarsaparilla) or Actigen Y from the company Actives Organics, or ginger.
- sapogenins wild yam rhizome, agave leaf, which contains hecogenin and tigogenin, extracts of Liliacea plants and more particularly yucca or smilax containing smilagenin and sarsapogenin, or sarsaparilla
- Actigen Y from the company Actives Organics, or ginger.
- DMAE dimethyl MEA
- extracts of sea fennel of rockrose, of helichrysum, of aniseed, of paracress
- Gatuline® from Gattefosse
- Preferred dermo-relaxing agents that will be mentioned include adenosine, manganese gluconate, wild yam, sea fennel, glycine and alverine.
- anti-glycation agent means a compound that prevents and/or reduces the glycation of skin proteins, in particular dermal proteins such as collagen.
- Anti-glycation agents that may especially be mentioned include extracts of plants of the Ericacea family, such as an extract of blueberry (Vaccinium angustifolium or Vaccinium myrtillus) , for example the product sold under the name Blueberry Herbasol Extract PG by the company Cosmetochem, ergothioneine and derivatives thereof, hydroxystilbenes and derivatives thereof, such as resveratrol and 3, 3' , 5, 5' -tetrahydroxystilbene (these anti-glycation agents are described in patent applications FR 2 802 425, FR 2 810 548, FR 2 796 278 and FR 2 802 420, respectively), dihydroxystilbenes and derivatives thereof, polypeptides of arginine and of lysine such as the product sold under the name Amadorine® by the company Solabia, carsinine hydrochloride (sold by Exsymol under the name Austin®) , an extract of Helianthus annuus, for instance Antiglys
- Preferred anti-glycation agents include extracts of blueberry (Vaccinium myrtillus) and extracts of black tea.
- active agents for stimulating the dermal macromolecules or for preventing their degradation mention may be made of those acting: - either on collagen synthesis, such as extracts of Centella asiatica, asiaticosides and derivatives thereof; ascorbic acid or vitamin C and derivatives thereof; synthetic peptides such as iamin, biopeptide CL or palmitoyl oligopeptide sold by the company Sederma; peptides extracted from plants, such as the soybean hydrolysate sold by the company Coletica under the trade name Phytokine®; rice peptides such as Nutripeptide® from Silab, methylsilanol mannuronate such as Algisium C® sold by Exsymol; plant hormones such as auxins and lignans; folic acid; and an extract of Medicago sativa (alfalfa) such as the product sold by Silab under the name Vitanol®; a peptide extract of hazelnut such as the product sold by the company Solabia
- elastin and fibrillin molecules belonging to the elastin family (elastin and fibrillin), such as: retinol and derivatives, in particular retinyl palmitate; the extract of Saccharomyces cerevisiae sold by the company LSN under the trade name Cytovitin®; and the extract of the alga Macrocystis pyrifera sold by the company Secma under the trade name Kelpadelie®; a peptide extract of hazelnut such as the product sold by the company Solabia under the trade name Nuteline C®;
- elastin degradation such as the peptide extract of seeds of Pisum sativum sold by the company LSN under the trade name Parelastyl®; heparinoids; and the N-acylamino acid compounds described in patent application WO 01/94381, such as ⁇ 2- [acetyl (3-trifluoromethylphenyl) amino] -3-methyl- butyrylamino ⁇ acetic acid, also known as N-[N-acetyl, N' - (3-trifluoromethyl) phenylvalyl] glycine, or N-acetyl- N- [3- (trifluoromethyl) phenyl] valyl glycine or acetyl trifluoromethyl phenyl valylglycine, or an ester thereof with a Ci-C ⁇ alcohol; an extract of rice peptides such as Colhibin® from Pentapharm, or an extract of Phyllanthus emblica such as Emblic
- glycosaminoglycans such as the product of fermentation of milk with Lactobacillus vulgaris, sold by the company Brooks under the trade name Biomin Yoghurt®; the extract of the brown alga Padina pavonica sold by the company Alban Muller under the trade name HSP3®; the Saccharomyces cerevisiae extract available especially from the company Silab under the trade name Firmalift® or from the company LSN under the trade name Cytovitin®; an extract of Laminaria ochroleuca such as Laminaine® from Secma; essence of Mamaku from Lucas Meyer, and an extract of Cress (Odraline® from Silab) ; - or on the synthesis of fibronectin, such as the extract of the zooplankton Salina sold by the company Seporga under the trade name GP4G®; the yeast extract available especially from the company Alban Muller under the trade name Drieline®; and the palmitoyl pentapeptide sold by the
- the active agents for stimulating epidermal macromolecules such as fillagrin and keratins
- an active agent that stimulates the synthesis of dermal and/or epidermal macromolecules and/or that prevents their degradation chosen from agents for stimulating the synthesis of glycosaminoglycans, agents for inhibiting elastin degradation, agents for stimulating fibronectin synthesis, agents for stimulating the synthesis of epidermal macromolecules, and mixtures thereof, will preferably be used.
- an active agent that stimulates the synthesis of the glycosaminoglycans chosen from an extract of the brown alga Padina pavonica, an extract of Saccharomyces cerevisiae, an extract of Laminaria ochroleuca, essence of Mamaku, and an extract of cress, and mixtures thereof, will even more preferentially be used.
- active agents for stimulating the synthesis of dermal and/or epidermal macromolecules and/or for preventing their degradation mention may be made of: synthetic peptides such as iamin, the biopeptide CL or palmitoyloligopeptide sold by the company Sederma; peptides extracted from plants, such as the soybean hydrolysate sold by the company Coletica under the trade name Phytokine®; rice peptides such as Nutripeptide® from Silab, methylsilanol mannuronate such as Algisium C® sold by Exsymol; folic acid; an extract of Medicago sativa (alfalfa) , such as the product sold by Silab under the name Vitanol®; a peptide extract of hazelnut, such as the product sold by the company Solabia under the name Nuteline C®; arginine; an extract of Aphanizomenon flos-aquae
- the agents for stimulating fibroblast proliferation may be chosen, for example, from plant proteins or polypeptides, extracted especially from soybean (for example a soybean extract sold by the company LSN under the name Eleseryl SH-VEG 8® or sold by the company Silab under the trade name Raffermine®) ; an extract of hydrolysed soybean proteins such as Ridulisse® from Silab; and plant hormones such as gibberellins and cytokinins; a peptide extract of hazelnut such as the product sold by the company Solabia under the name Nuteline C®.
- soybean for example a soybean extract sold by the company LSN under the name Eleseryl SH-VEG 8® or sold by the company Silab under the trade name Raffermine®
- an extract of hydrolysed soybean proteins such as Ridulisse® from Silab
- plant hormones such as gibberellins and cytokinins
- a peptide extract of hazelnut such as the product sold by the company Solabia under the name Nuteline C®.
- an agent that promotes keratinocyte proliferation and/or differentiation will be used.
- the agents for stimulating keratinocyte proliferation that may be used in the composition according to the invention especially comprise adenosine; phloroglucinol, the extract of Hydrangea macrophylla leaves, for instance Amacha Liquid E® from Ichimaru Pharcos, a yeast extract such as Stimoderm® from CLR; the extract of Larrea divaricata such as Capislow® from Sederma, mixtures of extract of papaya, of olive leaves and of lemon, such as Xyleine® from Vincience, the extract of Hydrangea macrophylla leaves, for instance Amacha Liquid E® from Ichimaru Pharcos, retinol and esters thereof, including retinyl palmitate, phloroglucinol, the nut cake extracts sold by the Gattefosse and the extracts of Solanum tuberosum such as Dermolectine® sold by Sederma.
- adenosine phloroglucinol
- agents for stimulating keratinocyte differentiation are, for example, minerals such as calcium; sea fennel, a peptide extract of lupin, such as the product sold by the company Silab under the trade name Structurine®; sodium beta-sitosteryl sulfate, such as the product sold by the company Seporga under the trade name Phytocohesine®; and a water-soluble extract of corn, such as the product sold by the company Solabia under the trade name Phytovityl®; a peptide extract of Voandzeia substerranea such as the product sold by the company Laboratoires Serobi unanimouss under the trade name Filladyn LS 9397®; and lignans such as secoisolariciresinol, and retinol and esters thereof, including retinyl palmitate.
- minerals such as calcium
- sea fennel a peptide extract of lupin
- Structurine® sodium beta-sitosteryl s
- oestrogens such as oestradiol and homologues
- cytokines cytokines
- plant proteins or polypeptides extracted especially from soybean (for example a soybean extract sold by the company LSN under the name Eleseryl SH-VEG 8® or sold by the company Silab under the trade name Raffermine®) ; an extract of hydrolysed soybean proteins such as Ridulisse® from Silab; a peptide extract of hazelnut such as the product sold by the company Solabia under the name Nuteline C®; adenosine; phloroglucinol, a yeast extract such as Stimoderm® from CLR; a peptide extract of lupin such as the product sold by the company Silab under the trade name Structurine®; a water-soluble corn extract, such as the product sold by the company Solabia under the trade name Phytovityl®; a peptide extract of Voandzeia substerranea, such as the product sold by the company Laboratoire
- Agents that participate in the maturation of the horny envelope, which becomes impaired with age and induces a decrease in transglutaminase activity may be used in the compositions of the invention.
- Examples that may be mentioned include urea and derivatives thereof and in particular Hydrovance® from National Starch and the other active agents mentioned in L'Oreal patent application FR 2 877 220 (unpublished) .
- the agent with an inhibitory action on NO synthase may be chosen from OPCs (procyannidol oligomers) ; plant extracts of the species Vitis vinifera sold especially by the company Euromed under the name "Leucocyanidines de raisins extra", or by the company Indena under the name Leucoselect®, or finally by the company Hansen under the name "Extrait de marc de raisin”; plant extracts of the species Olea europaea preferably obtained from olive tree leaves and sold especially by the company Vinyals in the form of a dry extract, or by the company Biologia & Technologia under the trade name Eurol BT; and plant extracts of the species Gingko biloba, preferably a dry aqueous extract of this plant sold by the company Beaufour under the trade name "Ginkgo biloba 1% standard", and mixtures thereof.
- OPCs procyannidol oligomers
- PBR Peripheral benzodiazepine receptor
- Mention may be made, for example, of methyl dehydroj asmonate, hecogenin, hedione and 0-linoleyl-6D- glucose, and mixtures thereof.
- the active agent for stimulating the energy metabolism of cells may be chosen, for example, from biotin, an extract of Saccharomyces cerevisiae such as Phosphovital® from Sederma, the mixture of sodium, manganese, zinc and magnesium salts of pyrrolidonecarboxylic acid, for instance Physiogenyl® from Solabia, a mixture of zinc, copper and magnesium gluconate, such as Sepitonic M3® from SEPPIC, and mixtures thereof; a beta-glucan derived from Saccharomyces cerevisiae, such as the product sold by the company Mibelle AG Biochemistry.
- tensioning agent means compounds liable to have a tensioning effect, i.e. being able to make the skin taut .
- the term “tensioning agent” generally means any polymer that is soluble or dispersible in water at a temperature ranging from 25°C to 50 0 C at a concentration of 7% by weight in water or at the maximum concentration at which a medium of uniform appearance is formed and producing at this concentration of 7% or at this maximum concentration in water a shrinkage of more than 15% in the test described below.
- the maximum concentration at which a medium of uniform appearance forms is determined to within ⁇ 10% and preferably to within ⁇ 5%.
- the expression "medium of uniform appearance” means a medium that does not contain any aggregates that are visible to the naked eye.
- the tensioning agent is gradually added to the water with deflocculating stirring at a temperature ranging from 25°C to 50 0 C, and the mixture is then stirred for one hour.
- the mixture thus prepared is then examined after 24 hours to see if it is of uniform appearance (absence of aggregates visible to the naked eye) .
- the tensioning effect may be characterized by an in vitro shrinkage test.
- a homogeneous mixture of the tensioning agent in water, at a concentration of 7% by weight or at the maximum concentration defined above, is prepared beforehand and as described previously.
- the elastomer sample After drying for 3 hours at 22 ⁇ 3°C and 40 ⁇ 10% relative humidity RH, the elastomer sample has a shrunken width, noted L 3h , due to the tension exerted by the applied tensioning agent.
- TE tensioning effect
- L 3h width after 3 hours of drying.
- the tensioning agent may be chosen from: plant or animal proteins and hydrolysates thereof; polysaccharides of natural origin; mixed silicates; colloidal particles of mineral fillers; synthetic polymers; and mixtures thereof.
- plant proteins and protein hydrolysates in particular of corn, rye, wheat, buckwheat, sesame, spelt, pea, bean, lentil, soybean and lupin,
- polysaccharides of natural origin especially (a) polyholosides, for example (i) in the form of starch derived especially from rice, corn, potato, cassava, pea, wheat, oat, etc. or (ii) in the form of carrageenans, alginates, agars, gellans, cellulose polymers and pectins, advantageously as an aqueous dispersion of gel microparticles, and (b) latices consisting of shellac resin, sandarac gum, dammar resins, elemi gums, copal resins, cellulose derivatives, and mixtures thereof,
- colloidal particles of mineral fillers with a number-average diameter of between 0.1 and 100 nm and preferably between 3 and 30 nm, and chosen, for example, from: silica, silica-alumina composites, cerium oxide, zirconium oxide, alumina, calcium carbonate, barium sulfate, calcium sulfate, zinc oxide and titanium dioxide.
- silica-alumina composite colloidal particles that may be used in the compositions according to the invention, examples that may be mentioned include those sold by the company Grace under the names Ludox AM, Ludox AM-X 6021, Ludox HSA and Ludox TMA,
- synthetic polymers such as polyurethane latices or acrylic-silicone latices, in particular those described in patent application EP-I 038 519, such as a polydimethylsiloxane grafted with propylthio (polymethyl acrylate) , propylthio (polymethyl methacrylate) and propylthio (polymethacrylic acid) , or alternatively a polydimethylsiloxane grafted with propylthio (polyiso- butyl methacrylate) and propylthio (polymethacrylic acid) .
- grafted silicone polymers are especially sold by the company 3M under the trade names VS 80, VS 70 and LO21.
- the tensioning agent will be present in the composition in an amount that is effective for obtaining the desired biological effect according to the invention.
- the tensioning agent may be included in the composition according to the invention in a content ranging from 0.01% to 30% by weight of active material and preferably from 1% to 30% by weight of active material relative to the total weight of the composition .
- active material is intended to exclude the medium in which the tensioning agent may be dissolved or dispersed in its commercial form, for example in the case of dispersions of colloidal particles.
- agents that increase the expression of mechanoreceptors such as agents that increase the expression of integrins .
- An example that may be mentioned is an extract of rye seed, such as the product sold by Silab under the name Coheliss®.
- fat-restructuring agents means agents capable of stimulating lipogenesis and of promoting adipocyte differentiation, thus making it possible to prevent or slow down the wasting of fat contained in the skin supporting tissues, also known as "wasting of skin fat”.
- skin fat means the network of fat cells that form the volumes on which the facial skin rests and is moulded.
- These agents are intended to reduce the loss of skin density and/or the wasting of skin fat, in particular on the cheeks and around the eyes, and/or to prevent the collapse and/or hollowing of the facial volumes, the loss of consistency of the skin and/or its maintenance, in particular on the cheeks and around the eyes, and/or to improve the underlying volumes of the skin of the face and/or the neck, in particular on the cheeks, the oval of the face and around the eyes, and/or to improve the density, springiness and maintenance of the skin, in particular on the cheeks, the oval of the face and around the eyes, and/or to remodel the facial features, in particular the oval of the face .
- fat-restructuring agents examples include an extract of black tea, such as the extract of fermented black tea sold by Sederma under the name Kombuchka®, and an extract of Artemisia abrotanum, such as the product sold by Silab under the name Pulpactyl®*
- Slimming agents that may especially be mentioned include theophylline and its derivatives, theobromine, acefylline, aminophylline, chloroethyl- theophylline, diprofylline, diniprophylline, etami- phylline and its derivatives, etofylline and proxyphylline; extracts of tea, of coffee, of guarana, of mate, of cola (Cola nitIda) and especially the dry extract of guarana fruit (Paulina sorbllls) containing 8% to 10% caffeine; extracts of climbing ivy (Hedera helix) , of arnica (Arnica montana L) , of rosemary (Rosmarinus officinalis N), of marigold (Calendula officinalis) , of sage (Salvia officinalis L) , of ginseng (Panax ginseng) ,
- the active agent acting on the cutaneous microcirculation may be used for preventing dulling of the complexion and/or to improve the appearance of the area around the eyes, in particular to reduce the shadows around the eyes. It may be chosen, for example, from an extract of maritime pine bark, for instance Pycnogenol® from Bio prises, manganese gluconate (Givobio GMn® from SEPPIC) , an extract of Ammi visnaga such as Visnadine from Indena, extract of lupin (Eclaline® from Silab) , the protein coupling of hydrolysed wheat/palmitic acid with palmitic acid, such as Epaline 100 from Laboratoires Carilene, the extract of bitter orange blossom (Remoduline® from Silab) , vitamin P and derivatives thereof, for instance methyl-4 esculetol sodium monoethanoate sold under the name Permethol® by the company Sephytal, extracts of Ruscus, of common horse chestnut, of ivy, of ginseng and of
- caffeine As preferred agents for promoting the cutaneous microcirculation, mention will be made of caffeine, an extract of bitter orange blossom, an extract of black tea, rutin salts and an extract of the alga Corallina officinalis .
- the term “calmative” means a compound that can reduce the sensation of stinging, itching or tautness of the skin .
- procyannidol oligomers vitamins E, C, B5 and B3, caffeine and derivatives thereof, pentacylic triterpenes and plant extracts containing them, ⁇ -glycyrrhetinic acid and salts or derivatives thereof (stearyl glycyrrhetate, 3-stearoyloxyglycyrrhetic acid or glycyrrhetinic acid monoglucuronide) and also plants containing them (e.g.: Glycyrrhiza glabra) , oleanolic acid and salts thereof, ursolic acid and salts thereof, boswellic acid and salts thereof, betulinic acid and salts thereof, an extract of Paeonia suffruticosa and/or lactiflora, an extract of Laminaria saccharina, extracts of Centella asiatica, Canola oil, bisabolo
- ⁇ -glycyrrhetinic acid and salts or derivatives thereof stearyl glycyrrhetate, 3-stearoyloxyglycyrrhetic acid or glycyrrhetinic acid monoglucuronide
- plants containing them e.g.
- Glycyrrhiza glabra ursolic acid and salts thereof; extracts of Centella asiatica, Canola oil, bisabolol; camomile extracts, allantoin; a mixture of extract of water lily blossom and of palmitoylproline, such as the product sold under the name Seppicalm VG® by the company SEPPIC; Aloe vera, rose water, extract of mint, in particular of mint leaves, filamentous bacteria such as Vitreoscilla filiformis as described in patent EP 761 204 and sold by Chimex under the name Mexoryl SBG®, an extract of rose petals such as Rose Flower Herbasol® extract from the company Cosmetochem, shea butter, a fermented extract of Alteromonas sold under the name Abyssine® by the company Atrium Biotechnologies; spring water from the Vichy basin, such as waters originating from the Celestin, Chomel, Grande-Grille,
- Sebo-regulating or anti-seborrhoeic agents especially means agents capable of regulating the activity of the sebaceous glands.
- SEPPIC the mixture of cinnamon, sarcosine and octanoylglycine sold especially by the company SEPPIC under the trade name Sepicontrol A5®; - zinc salts such as zinc gluconate, zinc pyrrolidonecarboxylate (or zinc pidolate) , zinc lactate, zinc aspartate, zinc carboxylate, zinc salicylate and zinc cysteate;
- Phellodendron extracts such as those sold under the name Phellodendron extract BG by the company Maruzen or Oubaku liquid B by the company Ichimaru Pharcos;
- Terminalia chebula of nasturtium and of bioavailable zinc (microalgae) , such as the product sold under the name Seborilys® by the company Green Tech; extracts of Pygeum afrianum, such as the product sold under the name Pygeum afrianum sterolic lipid extract by the company Euromed;
- Serenoa serrulata such as the products sold under the name Viapure Sabal by the company Actives International or those sold by the company Euromed;
- - sugar cane extracts such as the product sold under the name Policosonol® by the company Sabinsa; sulfonated shale oil, such as the product sold under the name Ichthyol Pale® by the company Ichthyol;
- - sebacic acid especially sold in the form of a sodium polyacrylate gel under the name Sebosoft® by the company Sederma; - glucomannans extracted from konjac tuber and modified with alkylsulfonate chains, such as the product sold under the name Biopol Beta by the company Arch Chemical; extracts of Sophora angustifolia, such as those sold under the name Sophora powder or Sophora extract by the company Bioland;
- Preferred anti-seborrhoeic active agents include: - benzoyl peroxide and vitamin B6 (or pyridoxine) , zinc salts such as zinc gluconate, zinc pyrrolidonecarboxylate (or zinc pidolate) , zinc lactate, zinc aspartate, zinc carboxylate, zinc salicylate and zinc cysteate;
- - sebacic acid especially sold in the form of a sodium polyacrylate gel under the name Sebosoft® by the company Sederma; glycine grafted onto an undecylenic chain, such as the product sold under the name Lipacide UG OR by the company SEPPIC; - tri (C12-C13) alkyl citrate sold under the name
- Cosmacol® ECI by the company Sasol
- tri (Ci 4 -Ci 5 ) alkyl citrate sold under the name Cosmacol® ECL by the company Sasol
- 10-hydroxydecanoic acid and especially mixtures of 10-hydroxydecanoic acid, of sebacic acid and of 1, 10-decanediol, such as the product sold under the name Acnacidol® BG by the company Vincience; and - mixtures thereof.
- the anti-seborrhoeic active agent is chosen from: zinc salts such as zinc gluconate, zinc pyrrolidonecarboxylate (or zinc pidolate) , zinc lactate, zinc aspartate, zinc carboxylate, zinc salicylate and zinc cysteate; and preferably zinc pyrrolidonecarboxylate (or zinc pidolate) or zinc salicylate; - clove extract, such as the product sold under the name Clove extract powder by the company Maruzen;
- Cosmacol® ECI by the company Sasol
- tri (Ci 4 -Ci 5 ) alkyl citrate sold under the name Cosmacol® ECL by the company Sasol
- the anti-seborrhoeic active agent is, for example, present in a content ranging from 0.1% to 10% by weight, preferably from 0.1% to 5% by weight and preferentially from 0.5% to 3% by weight relative to the total weight of the composition.
- astringents means agents for combating the dilation of the sebaceous follicles.
- extracts of mushroom pulp for instance Laricyl LS8865® from Cognis, extracts of Terminalia catappa and Sambucus nigra, for instance Phytofirm LS9120® from Cognis, extracts of gall nut, for instance Tanlex VE® from Ichimaru Pharcos, aluminium hydroxychloride, centella extracts (e.g.
- Plantactiv centella from Cognis dicetyl dimethylammonium chloride, for instance Varisoft 432 CG® from Degussa, common horse chestnut extracts, mallow extracts, witch-hazel extracts, sweet almond extracts, marshmallow root extracts and linseed extracts, for instance Almondermin LS 3380® from Cognis, burdock extracts, nettle extracts, birch extracts, horsetail extracts, camomile extracts, for instance those sold under the name Extrapone 9 special® by the company Symrise, skullcap extracts, European meadowsweet extracts (for example Cytobiol Ulmaire from Libiol) , a mixture of extracts of white ginger, of horsetail, of nettle, of rosemary and of yucca, for instance Herb extract B1348® from Bell Flavors & Fragrances, extracts of acacia, of elm, of white willow, of cinnamon, of birch and of meadowsweet, Panama sapogenin
- skullcap extracts European meadowsweet extracts, meadowsweet extracts, gentian extracts and burdock extracts, and mixtures thereof.
- cicatrizing agents examples include: allantoin, urea, certain amino acids, for instance hydroxyproline, arginine, and serine, and also extracts of white lily (for instance Phytelene Lys 37EG 16295 from Indena) , a yeast extract, for instance the cicatrizing agent LS LO/7225B from Laboratoires Serobiiquess) , tamanu oil, extract of Saccharomyces cerevisiae, for instance Biodynes® TRF® from Arch Chemical, oat extracts, chitosan and derivatives, for instance chitosan glutamate, carrot extracts, artemia extract, for instance GP4G® from Vincience, sodium acexamate, lavandin extracts, propolis extracts, ximeninic acid and salts thereof, rose hip oil, marigold extracts, for instance Souci Ami® Liposolible from Alban Muller, horsetail extracts, lemon peel extracts, for instance Her
- cicatrizing agents use will be made of arginine, serine, folic acid, tamanu oil, sodium acexamate, horsetail extracts and helichrysum extracts, and mixtures thereof.
- anti-inflammatory agents that may be used according to the invention, mention may be made of cortisone, hydrocortisone, indomethacin, betamethasone, azelaic acid, acetaminophen, diclofenac, clobetasol propionate, folic acid; an extract of Eperua falcata bark, such as the product sold by the company Cognis under the name Eperuline®; an extract of Paeonia suffruticosa root, such as the product sold by the company Ichimaru Pharcos under the name Botanpi Liquid B®; and mixtures thereof.
- Preferred anti-inflammatory agents are azelaic acid, folic acid, an extract of Eperua falcata bark, such as the product sold by the company Cognis under the name Eperuline®; an extract of Paeonia suffruticosa root, such as the product sold by the company Ichimaru Pharcos under the name Botanpi Liquid B®; and mixtures thereof.
- the composition may also comprise at least one anti-acne active agent.
- antiacne active agent especially means any active agent that has effects on the specific flora of greasy skin, for instance Propionibacterium acnes (P. acnes) . These effects may be bactericidal.
- Antibactericidal active agents that may especially be mentioned include: - active agents and preserving agents with antimicrobial activity mentioned in patent application DE 103 24 567, which is incorporated into the present invention by reference,
- St. -John' s Wort extract obtained by supercritical CO2 extraction such as the product sold under the name St. -John's Wort CO2-TO extract® by the company Flavex Naturextrakte, the mixture of extracts of roots of Scutellaria baicalensis, of Paeonia suffruticosa and Glycyrrhiza glabra, such as the product sold under the name BMB - CF® by the company Naturogin, argan tree extract, for instance Argapure LS9710® from Cognis; bearberry leaf extracts, for instance the product sold under the name Melfade-J by the company Pentapharm;
- - lO-hydroxy-2-decanoic acid such as Acnacidol P® from Vincience, sodium ursolate, azelaic acid, diiodomethyl p-tolyl sulfone such as Amical Flowable® from Angus, malachite powder, zinc oxide such as Zincare® from Elementis GMBH, octadecenedioic acid such as Arlatone dioic DCA® from Uniqema; ellagic acid; 2, 4, 4' -trichloro-2' -hydroxydiphenyl ether (or triclosan) , 1- (3' , 4' -dichlorophenyl) -3- (4' -chloro- phenyl)urea (or triclocarban) , 3, 4, 4' -trichloro- carbanilide, 3' , 4' , 5' -trichlorosalicylanilide, phenoxy- ethanol, phenoxyprop
- betaines for instance the cocoyl betaine Genagen KB from Clariant, sodium lauryl ether sulfate, for instance Emal 270 D from Kao, decyl glucoside, for instance Plantacare 2000 UP, branched C12-13 dialkyl malates, for instance Cosmacol EMI, propylene glycol monoesters, for instance propylene glycol monolaurate, monocaprylate or monocaprate, lauryldimethylamine betaine, for instance Empigen BB/LS, and also polyquaternary ammoniums such as Quaternium-24 or Bardac 2050 from Lonza and those described in patent FR 0 108 283, and mixtures thereof.
- an agent chosen from caprylyl glycol, octoglycerine or octoxyglycerine, and 10-hydroxy-2-decanoic acid, and mixtures thereof, will be used in the compositions of the invention.
- anti-acne active agents may be added to the abovementioned anti-acne active agents. Mention may be made especially of active agents with bacterial anti-adhesion effects or agents that act on the biofilm of bacteria to prevent them from multiplying .
- phytanetriol and derivatives thereof as described in patent application EP 1 529 523, plant oils such as wheatgerm oil, calendula oil, castor oil, olive oil, avocado oil, sweet almond oil, groundnut oil, jojoba oil, sesame seed oil, apricot kernel oil, sunflower oil and macadamia oil, described in patent EP 1 133 979, or certain surfactants such as disodium cocoamphodiacetate, oxyethylenated (7 EO) glyceryl cocoate, 18-hexadecenyl succinate, octoxyglyceryl palmitate, octoxyglyceryl behenate, dioctyl adipate, PPG-15 stearyl ether, and the branched C12-C13 dialkyl tartrates described in patent EP 1 129 694, and mixtures thereof.
- plant oils such as wheatgerm oil, calendula oil, castor oil, olive oil, avocado oil, sweet almond oil, groundnut oil
- P. acnes or as active agents that act on the biofilm of bacteria to prevent them from proliferating, mention may be made of pentylene glycol, Nylon-66 (polyamide 66 fibres), rice bran oil, polyvinyl alcohol such as Celvol 540 PV alcohol® from Celanese Chemical, rapeseed oil such as Akorex L® from Karlshamns, and fructose derivatives, and mixtures thereof.
- the anti-acne active agent may be present in a content ranging from 0.01% to 10% by weight and preferably from 0.05% to 5% by weight relative to the total weight of the composition.
- lipophilic active agents that may be used in the kit or at least one of the compositions of the invention, mention may be made especially of D- ⁇ -tocopherol, DL- ⁇ - tocopherol, D- ⁇ -tocopheryl acetate, DL- ⁇ -tocopheryl acetate, ascorbyl palmitate, vitamin F glycerides, D vitamins, vitamin D2, vitamin D3, retinol, retinol esters, retinyl palmitate, retinyl propionate, carotenes including ⁇ -carotene, D-panthenol, farnesol, farnesyl acetate, salicylic acid and derivatives thereof, for instance 5-n-octanoylsalicylic acid, ⁇ - hydroxy acid alkyl esters such as citric acid, lactic acid, glycolic acid, asiatic acid, madecassic acid, asiaticoside, the total extract of Centella asiatica, ⁇ -glycyrrhetinic
- the cosmetic and/or dermatological active agents will be present in the kit or one of the compositions according to the invention in a content ranging from 0.001% to 20% relative to the total weight of the composition, preferably from 0.01% to 10%, even more preferentially from 0.5% to 5% and more preferably from 0.1% to 1% by weight relative to the total weight of the composition.
- the contents of cosmetic and/or dermatological active agents may range from 1% to 50% by weight relative to the total weight of the composition and preferably from 1% to 30% by weight relative to the total weight of the composition.
- Scrubbing is a well-known means for improving the appearance and/or texture of the skin and/or the scalp, especially for improving the radiance and homogeneity of the complexion and/or for reducing the visible and/or tactile irregularities of the skin, and in particular for improving the surface appearance of the skin, for attenuating actinic lentigo, acne or chicken pox marks, and also for preventing, attenuating or combating the signs of ageing of the skin, and especially for smoothing out irregularities in the texture of the skin, such as wrinkles and fine lines.
- compositions of the invention may be advantageous to incorporate into the compositions of the invention other additional ingredients.
- these additional ingredients may impart an immediate visual effect that will be relayed by the biological effect of the active agents mentioned above. They may also, via a mechanical action (e.g.: abrasive fillers) , amplify the effect of the biological active agents mentioned above.
- a mechanical action e.g.: abrasive fillers
- composition according to the invention may also comprise at least one agent chosen from matting agents, fillers with a soft-focus effect, fluorescers, agents for promoting the naturally pinkish coloration of the skin, abrasive fillers or exfoliants, and mixtures thereof.
- matting agent means agents intended to make the skin visibly more matt and less shiny.
- the matting effect of the agent and/or composition containing it may especially be evaluated using a gonioreflectometer, by measuring the ratio R between the specular reflection and the scattered reflection.
- a value of R of less than or equal to 2 generally reflects a matting effect.
- the matting agent may especially be chosen from a rice starch or a corn starch, kaolinite, talc, a pumpkin seed extract, cellulose microbeads, plant fibres, synthetic fibres, in particular polyamide fibres, expanded acrylic copolymer microspheres, polyamide powders, silica powders, polytetrafluoroethylene powders, silicone resin powders, acrylic polymer powders, wax powders, polyethylene powders, powders of elastomeric crosslinked organopolysiloxane coated with silicone resin, talc/titanium dioxide/alumina/silica composite powders, amorphous mixed silicate powders, silicate particles and especially mixed silicate particles, and mixtures thereof.
- matting agents examples include: rice or corn starch, in particular an aluminium starch octenyl succinate sold under the name Dry Flo® by the company National Starch;
- - talc a pumpkin seed extract as sold under the name Curbilene® by the company Indena; cellulose microbeads as described in patent application EP 1 562 562; - fibres, such as silk fibre, cotton fibre, wool fibre, flax fibre, cellulose fibre extracted especially from wood, from vegetables or from algae, polyamide fibre
- nylon® modified cellulose fibre, poly-p- phenyleneterephthamide fibre, acrylic fibre, polyolefin fibre, glass fibre, silica fibre, aramid fibre, carbon fibre, Teflon® fibre, insoluble collagen fibre, polyester fibre, polyvinyl chloride or polyvinylidene chloride fibre, polyvinyl alcohol fibre, polyacrylonitrile fibre, chitosan fibre, polyurethane fibre, polyethylene phthalate fibre, fibres formed from a mixture of polymers, resorbable synthetic fibres, and mixtures thereof described in patent application EP 1 151 742;
- polyamide powders Nylon®
- Nylon 12 particles of the Orgasol type from Arkema with a mean size of 10 microns and a refractive index of 1.54
- silica powders for instance Silica beads SB150 from Miyoshi with a mean size of 5 microns and a refractive index of 1.45
- - polytetrafluoroethylene powders for instance PTFE Ceridust 9205F from Clariant, with a mean size of 8 microns and a refractive index of 1.36
- silicone resin powders for instance the silicone resin Tospearl 145A from GE Silicone with a mean size of 4.5 microns and a refractive index of 1.41
- polyethylene powders especially comprising at least one ethylene/acrylic acid copolymer, and in particular consisting of ethylene/acrylic acid copolymers, for instance the particles Flobeads EA 209 from Sumitomo (with a mean size of 10 microns and a refractive index of 1.48) , elastomeric crosslinked organopolysiloxane powders coated with silicone resin, especially with silsesquioxane resin, as described, for example, in patent US 5 538 793.
- Such elastomeric powders are sold under the names KSP-100, KSP-101, KSP-102, KSP-103, KSP-104 and KSP-105 by the company Shin-Etsu, and talc/titanium dioxide/alumina/silica composite powders such as those sold under the name Coverleaf® AR-80 by the company Catalyst & Chemicals,
- silica powders for instance the porous silica microspheres sold under the name Silica Beads SB-700 sold by the company Miyoshi, the products Sunsphere® H51, Sunsphere® H33 and Sunsphere® H53 sold by the company Asahi Glass; the polydimethylsiloxane-coated amorphous silica microspheres sold under the name SA Sunsphere® H-33 and SA Sunsphere® H-53 sold by the company Asahi Glass; amorphous mixed silicate powders, especially of aluminium and magnesium, for instance the product sold under the name Neusilin UFL2 by the company Sumitomo; polyamide (Nylon®) powders, for instance Orgasol® 4000 sold by the company Arkema, and acrylic polymer powders, especially of polymethyl methacrylate, for instance Covabead® LH85
- - silicate particles such as alumina silicate
- - mixed silicate particles such as: - magnesium aluminium silicate particles, such as saponite or hydrated magnesium aluminium silicate with a sodium sulfate sold under the trade name Sumecton® by the company Kunimine;
- Preferred matting agents that may be used according to the invention include a pumpkin seed extract, a rice or corn starch, kaolinite, silicas, talc, polyamide powders, polyethylene powders, acrylic copolymer powders, expanded acrylic copolymer microspheres, silicone resin microbeads and mixed silicate particles, and mixtures thereof. Fillers with a soft-focus effect
- These fillers may be any material capable of modifying and hiding wrinkles by virtue of their intrinsic physical properties. These fillers may especially modify wrinkles via a tensioning effect, a covering effect or a soft-focus effect.
- fillers examples include the following compounds:
- silica beads SB150 and SB700 from Miyoshi with a mean size of 5 ⁇ m
- the series-H Sunspheres from Asahi Glass for instance Sunspheres H33, H51 with respective sizes of 3.5 and 5 ⁇ m;
- NLK 500®, NLK 506® and NLK 510® from Takemoto Oil and Fat, especially described in EP-A-I 579 849;
- silicone resin powders for instance the silicone resin Tospearl® 145A from GE Silicone, with a mean size of 4.5 ⁇ m;
- - polyethylene powders especially comprising at least one ethylene/acrylic acid copolymer, and in particular consisting of ethylene/acrylic acid copolymers, for instance the Flobeads® EA 209 particles from Sumitomo, with a mean size of 10 ⁇ m; - crosslinked elastomeric organopolysiloxane powders coated with silicone resin and especially with silsesquioxane resin, under the names KSP-100®, KSP-101®, KSP-102®, KSP-103®, KSP-104® and KSP-105® by the company Shin-Etsu;
- talc/titanium dioxide/alumina/silica composite powders for instance those sold under the name Coverleaf AR-80® by the company Catalyst & Chemicals;
- - hydrophilic or hydrophobic, synthetic or unnatural, mineral or organic fillers such as silk fibres, cotton fibres, wool fibres, flax fibres, cellulose fibres extracted especially from wood, vegetables or algae, Polyamides (Nylon®) fibres, modified cellulose fibres, poly-p-terephthamide fibres, acrylic fibres, polyolefin fibres, glass fibres, silica fibres, aramid fibres, carbon fibres, polytetrafluoroethylene (Teflon®) fibres, insoluble collagen fibres, polyester fibres, polyvinyl chloride fibres, polyvinylidene chloride fibres, polyvinyl alcohol fibres, polyacrylonitriles fibres, chitosan fibres, polyurethane fibres, polyethylene phthalate fibres, fibres formed from a mixture of polymers, resorbable synthetic fibres, and mixtures thereof described in patent application EP 1 151 742; spherical elastomeric crosslinked silicones, for instance
- the fillers with an effect on the signs of ageing are especially chosen from porous silica microparticles, hollow hemispherical silicones, silicone resin powders, acrylic copolymer powders, polyethylene powders, crosslinked elastomeric organopolysiloxane powders coated with silicone resin, talc/titanium dioxide/alumina/silica composite powders, precipitated calcium carbonate, magnesium carbonate, magnesium hydrogen carbonate, barium sulfate, hydroxyapatite, calcium silicate, cerium dioxide, glass or ceramic microcapsules, and silk fibres or cotton fibres, and mixtures thereof.
- the filler may be a soft-focus filler.
- soft-focus filler means a filler which in addition gives the complexion transparency and a hazy effect.
- the soft-focus fillers have a mean particle size of less than or equal to 15 microns. These particles may be in any form and in particular may be spherical or non-spherical. These fillers are more preferably non-spherical.
- the soft-focus fillers may be chosen from silica and silicate powders, especially alumina powder, powders of polymethyl methacrylate (PMMA) type, talc, silica/Tic ⁇ or silica/zinc oxide composites, polyethylene powders, starch powders, polyamide powders, styrene/acrylic copolymer powders and silicone elastomers, and mixtures thereof .
- silica and silicate powders especially alumina powder, powders of polymethyl methacrylate (PMMA) type, talc, silica/Tic ⁇ or silica/zinc oxide composites, polyethylene powders, starch powders, polyamide powders, styrene/acrylic copolymer powders and silicone elastomers, and mixtures thereof .
- talc with a number-average size of less than or equal to 3 microns for example talc with a number-average size of 1.8 microns and especially the product sold under the trade name Talc P3® by the company Nippon Talc, Nylon® 12 powder, especially the product sold under the name Orgasol 2002 Extra D Nat Cos® by the company Atochem, silica particles 1% to 2% surface-treated with a mineral wax (INCI name: hydrated silica (and) paraffin) such as the products sold by the company Degussa, amorphous silica microspheres, such as the products sold under the name Sunsphere, for example of reference H-53® by the company Asahi Glass, and silica microbeads such as those sold under the name SB-700® or SB-150® by the company Miyoshi, this list not being limiting.
- a mineral wax INCI name: hydrated silica (and) paraffin
- amorphous silica microspheres such as the products
- the concentration of these fillers with an effect on the signs of ageing in the compositions according to the invention may be between 0.1% and 40%, or even between 0.1% and 20% by weight, relative to the total weight of the composition.
- fluorescer means a substance which, under the effect of ultraviolet rays and/or visible light, re-emits in the visible region the portion of light that it has absorbed under the same colour as that which it naturally reflects. The naturally reflected colour is thus reinforced by the re-emitted colour and appears extremely bright.
- fluorescent pigments examples include coloured polyamide and/or formaldehyde/benzoguanamine and/or melamine/formaldehyde/sulfonamide resins, from coloured aminotriazine/formaldehyde/sulfonamide co-condensates and/or from metallized polyester flakes and/or mixtures thereof.
- These fluorescent pigments may also be present in the form of aqueous dispersions of fluorescent pigments .
- the fluorescent substances are preferably present in the composition in a content ranging from 0.1% to 20%, preferably from 0.1% to 15% and more preferably from 0.5% to 3% by weight relative to the total weight of the composition.
- organic fluorescent substances are white, they are also known as optical brighteners .
- the optical brightener has the effect of intensifying the radiance and reviving the shades of cosmetic compositions comprising them on application to the skin.
- optical brighteners that may be mentioned more particularly are stilbene derivatives, in particular polystyrylstilbenes and triazinestilbenes, coumarin derivatives, in particular hydroxycoumarins and aminocoumarins, oxazole, benzoxazole, imidazole, triazole and pyrazoline derivatives, pyrene derivatives and porphyrin derivatives, and/or mixtures thereof.
- stilbene derivatives in particular polystyrylstilbenes and triazinestilbenes
- coumarin derivatives in particular hydroxycoumarins and aminocoumarins
- oxazole benzoxazole
- imidazole triazole and pyrazoline derivatives
- pyrene derivatives and porphyrin derivatives and/or mixtures thereof.
- Such compounds are available, for example, under the trade names Tinopal SOP® and Uvitex OB® from the company Ciba Geigy.
- optical brighteners preferentially used are sodium 4, 4' -bis [ (4, 6-dianilino-l, 3, 5-triazin-2-yl) amino] - stilbene-2, 2' -disulfonate, 2, 5-thiophenediylbis (5-tert- butyl-1, 3-benzoxazole) and disodium 4, 4' -distyrylbi- phenylsulfonate, and/or mixtures thereof.
- a self-tanning agent i.e. an agent which, when applied to the skin, especially to the face, can produce a tan effect that is more or less similar in appearance to that which may result from prolonged exposure to the sun (natural tan) or under a UV lamp;
- an additional colouring agent i.e. any compound that has particular affinity for the skin, which allows it to give the skin a lasting, non-covering coloration
- Such a lasting coloration is thus distinguished from the superficial and transient coloration provided, for example, by a makeup pigment; and mixtures thereof.
- DHA dihydroxyacetone
- erythrulose erythrulose
- catalytic system formed from:
- the self-tanning agents are generally chosen from monocarbonyl or polycarbonyl compounds, for instance isatin, alloxan, ninhydrin, glyceraldehyde, mesotartaric aldehyde, glutaraldehyde, erythrulose, pyrazoline-4, 5-dione derivatives as described in patent application FR 2 466 492 and WO 97/35842, dihydroxy- acetone (DHA) and 4, 4-dihydroxypyrazolin-5-one derivatives as described in patent application EP 903 342. DHA will preferably be used.
- isatin isatin, alloxan, ninhydrin, glyceraldehyde, mesotartaric aldehyde, glutaraldehyde, erythrulose, pyrazoline-4, 5-dione derivatives as described in patent application FR 2 466 492 and WO 97/35842, dihydroxy- acetone (DHA) and 4,
- the DHA may be used in free and/or encapsulated form, for example in lipid vesicles such as liposomes, especially described in patent application WO 97/25970.
- the self-tanning agent is present in an amount ranging from 0.01% to 20% by weight and preferably in an amount of between 0.1% and 10% of the total weight of the composition.
- These dyes may be chosen from synthetic or natural direct dyes.
- dyes may be chosen, for example, from red or orange dyes of the fluorane type such as those described in patent application FR 2 840 806. Mention may be made, for example, of the following dyes:
- CTFA name CI 45380 or Red 21
- - phloxin B known under the CTFA name: CI 45410 or Red 27;
- These dyes may also be chosen from anthraquinones, caramel, carmine, carbon black, azulene blues, methoxalene, trioxalene, guajazulene, chamuzulene, rose Bengal, eosin 1OB, cyanosin and daphinin.
- dyes may also be chosen from indole derivatives, for instance the monohydroxyindoles as described in patent FR 2 651 126 (i.e.: 4-, 5-, 6- or 7-hydroxy- indole) or the dihydroxyindoles as described in patent FR 2 651 126 (i.e.: 4-, 5-, 6- or 7-hydroxy- indole) or the dihydroxyindoles as described in patent FR 2 651 126 (i.e.: 4-, 5-, 6- or 7-hydroxy- indole) or the dihydroxyindoles as described in patent
- EP-B-O 425 324 i.e.: 5, 6-dihydroxyindole, 2-methyl-
- exfoliants for scrubbing particles of mineral, plant or organic origin.
- polyethylene beads or powder Nylon powder, polyvinyl chloride powder, pumice powder, ground apricot kernel or walnut husk, sawdust, glass beads and alumina, and mixtures thereof, may be used, for example.
- Exfogreen® from Solabia (bamboo extract)
- extracts of strawberry akenes may also be made of Exfogreen® from Solabia (bamboo extract) , extracts of strawberry akenes
- peach kernel powder As abrasive fillers or exfoliants that are preferred according to the invention, mention will be made of peach kernel powder, apricot kernel powder, cranberry kernel powder, strawberry akene extracts and bamboo extracts .
- composition ingredients are given as weight percentages relative to the total weight of the composition.
- compositions are prepared:
- the photostability of the dibenzoylmethane derivatives is studied on formulations 1 to 5 in which the content of benzoate derivatives is varied.
- the support common to these formulations is as follows:
- test plates are exposed for 43 minutes to a Heraeus Sun-Test machine fitted with a xenon lamp having a UV-A flux of 8.34*10 ⁇ J W/cirT and a UV-A B flux of 0.471x10 -4 W/cm 2 .
- the control plates are stored for the same time at the same temperature (38-40 0 C) in darkness.
- the screening agents are extracted by immersing each plate in 50 g of methanol and subjecting them to ultrasonication for 15 minutes to ensure good extraction.
- the solutions obtained are analysed by HPLC and UV spectrophotometry.
- the residual content of 4-tert- butyl-4' -methoxydibenzoylmethane after exposure is given as the ratio of its optical density (OD) in the exposed sample to its non-exposed optical density (OD) .
- OD optical density
- ⁇ max 358 nm
- formula 5 as defined previously comprising 20% of 2-hexyldecyl N-myristoyl-N- methylaminopropionate (Amiter MA-HD) is compared with a formula 6 of the prior art identical to formula 5 but containing, instead of the Amiter MA-HD: 20% of ethyl N-butyl-N-acetylaminopropionate (R3535) .
- the viscosity of each emulsion 10 minutes after its manufacture is measured: the measurement is taken using an RM180 model viscometer from the company Mettler. The measurements are performed in a bath thermostatically maintained at 25°C with a No. 2 or 3 measuring spindle depending on the viscosity of the product.
- the percentage loss of dibenzoylmethane derivative induced by exposure to a solar simulator of a formula spread as a film about 20 ⁇ m thick is measured.
- the evaluation is performed by HPLC analysis of the screening agent in solution, after extraction of the films, by comparing the irradiated and non-irradiated samples .
- UV-meter Osram Centra machine equipped with two reading heads, one for UVA the other for UVB.
- the simulator/UV-meter assembly is calibrated annually by spectroradiometry .
- Irradiance measurements taken at the start and end of exposure by placing the reading heads in the position of the sample.
- the irradiations are: 0.35-0.45 mW/cm 2 in UVB 16-18 mW/cm 2 in UVA.
- each support disc is placed in a 600 ml jar with 10 ml of a suitable solvent (generally EtOH) ; the whole is placed for 5 minutes in an ultrasonication tank.
- a suitable solvent generally EtOH
- the solution is then transferred into bottles adapted to the support that is compatible with the HPLC analysis machine used.
- the analytical conditions may be adjusted as a function of the active agent tested.
- the neutral N-acylamino acid ester derivatives (a) , (b) and (c) according to the invention have photostabilizing effects with respect to the dibenzoylmethane derivative that are higher than those obtained with the compounds of formulations 10 and 12.
- emulsions 7 to 9 according to the invention comprising, respectively, compounds (a) , (b) and (c) of the invention are stable, whereas emulsion 11 undergoes phase separation after a few days with ethyl N-butyl-N-acetylaminopropionate (R3535) as demonstrated previously.
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Abstract
La présente invention concerne une composition cosmétique contenant une combinaison d'au moins un dérivé de dibenzoylméthane et d'au moins un dérivé d'ester d'acide N-acylamino neutre particulier choisi parmi les composés (a) à (f) ci-dessous : (I). L'invention concerne également un procédé de stabilisation vis-à-vis du rayonnement et de la lumière d'au moins un dérivé de dibenzoylméthane par une quantité efficace d'au moins un ester d'acide N-acylamino neutre particulier, dérivé de la formule (a) à (f). La présente invention concerne également l'utilisation d'au moins un dérivé d'ester d'acide N-acylamino neutre particulier dérivé de la formule (a) à (f) dans une composition comportant, dans un support de qualité cosmétique, au moins un dérivé de dibenzoylméthane, dans le but d'améliorer l'efficacité de ladite composition en ce qui concerne la tenue au rayonnement UV-A.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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FR0850760 | 2008-02-06 | ||
FR0850760A FR2926980A1 (fr) | 2008-02-06 | 2008-02-06 | Composition cosmetique contenant un derive de dibenzoylmethane et un derive ester d'aminioacide neutre n-acyle particulier ; procede de photostabilisation du derive de dibenzoylmethane |
US2840008P | 2008-02-13 | 2008-02-13 | |
US61/028,400 | 2008-02-13 |
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WO2009098139A1 true WO2009098139A1 (fr) | 2009-08-13 |
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PCT/EP2009/050859 WO2009098139A1 (fr) | 2008-02-06 | 2009-01-26 | Composition cosmétique contenant un dérivé de dibenzoylméthane et un dérivé d'ester d'acide n-acylamino neutre particulier ; procédé de photostabilisation du dérivé de dibenzoylméthane |
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Cited By (23)
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WO2011141110A2 (fr) | 2010-05-12 | 2011-11-17 | Merck Patent Gmbh | Photostabilisateurs |
WO2011141111A2 (fr) | 2010-05-12 | 2011-11-17 | Merck Patent Gmbh | Triazines utilisées comme accélérateurs de réaction |
DE102010044381A1 (de) | 2010-09-04 | 2012-03-08 | Merck Patent Gmbh | Farbstoff-Ascorbinsäurederivate |
WO2012065685A1 (fr) | 2010-11-19 | 2012-05-24 | Merck Patent Gmbh | Dérivés de l'acide ascorbique en tant que composants colorants d'oxydation |
EP2482159A2 (fr) | 2011-01-28 | 2012-08-01 | Honeywell International, Inc. | Procédés et systèmes reconfigurables pour optimiser la performance d'un système de maintenance basé sur des conditions |
DE102011010841A1 (de) | 2011-02-10 | 2012-08-16 | Merck Patent Gmbh | (1,3)-Dioxan-5-on-Verbindungen |
WO2013045016A2 (fr) | 2011-09-29 | 2013-04-04 | Merck Patent Gmbh | Oxydes de phosphane en tant qu'accélérateurs de réaction |
DE102011116165A1 (de) | 2011-10-14 | 2013-04-18 | Merck Patent Gmbh | Benzodioxepin-3-on-Verbindungen |
WO2013091775A2 (fr) | 2011-12-21 | 2013-06-27 | Merck Patent Gmbh | Utilisation de dérivés du cyclohéxanol comme principes actifs antimicrobiens |
WO2013159865A1 (fr) | 2012-04-25 | 2013-10-31 | Merck Patent Gmbh | Utilisation de dérivés de dicyclohexyl-méthanol présentant des propriétés antimicrobiennes |
WO2013167220A1 (fr) | 2012-05-08 | 2013-11-14 | Merck Patent Gmbh | Utilisation de dérivés de cyclohexanol-éther à propriétés antimicrobiennes |
DE102012016960A1 (de) | 2012-08-28 | 2014-03-06 | Merck Patent Gmbh | Aminoester von Aminosäuren als Reaktionsbeschleuniger |
DE102012016194A1 (de) | 2012-08-16 | 2014-03-13 | Merck Patent Gmbh | Verwendung von Dicyclohexylmethanolderivaten mit antimikrobiellen Eigenschaften |
DE102012016191A1 (de) | 2012-08-16 | 2014-03-13 | Merck Patent Gmbh | Verwendung von Cyclohexanolethern mit antimikrobiellen Eigenschaften |
WO2014090364A1 (fr) | 2012-12-13 | 2014-06-19 | Merck Patent Gmbh | Quinones substituées ou analogues utilisés comme colorants |
WO2014127882A1 (fr) | 2013-02-25 | 2014-08-28 | Merck Patent Gmbh | Dérivés de glucuronolactone utilisés comme substances autobronzantes |
US8877713B2 (en) | 2009-01-09 | 2014-11-04 | Isp Investments | Anti-aging peptides and cosmetic and/or pharmaceutical composition containing same |
WO2016142026A1 (fr) | 2015-03-06 | 2016-09-15 | Merck Patent Gmbh | Tensioactifs fluorés situés dans des émulsions |
WO2017008877A1 (fr) | 2015-07-14 | 2017-01-19 | Merck Patent Gmbh | Compositions d'agents tensioactifs fluorés et d'antioxydants |
WO2018162368A1 (fr) | 2017-03-06 | 2018-09-13 | Merck Patent Gmbh | Utilisation de solutés compatibles |
KR20190064054A (ko) * | 2017-11-30 | 2019-06-10 | (주)아모레퍼시픽 | Low pH의 효능 물질을 포함하며 안정도가 향상된 유화 조성물 |
WO2021018990A1 (fr) | 2019-08-01 | 2021-02-04 | Merck Patent Gmbh | Prévention et réduction des troubles de la kératinisation, et agents cosmétiques associés |
WO2025024904A1 (fr) * | 2023-07-28 | 2025-02-06 | L'oreal | Composition cosmétique, utilisation de la composition cosmétique et procédé de fabrication de la composition cosmétique |
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FR2972348B1 (fr) * | 2011-03-09 | 2013-03-08 | Oreal | Composition cosmetique contenant un derive de dibenzoylmethane et un compose monoester monoamide d'acide methyl succinique ; procede de photostabilisation |
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Cited By (26)
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US8877713B2 (en) | 2009-01-09 | 2014-11-04 | Isp Investments | Anti-aging peptides and cosmetic and/or pharmaceutical composition containing same |
WO2011141110A2 (fr) | 2010-05-12 | 2011-11-17 | Merck Patent Gmbh | Photostabilisateurs |
WO2011141111A2 (fr) | 2010-05-12 | 2011-11-17 | Merck Patent Gmbh | Triazines utilisées comme accélérateurs de réaction |
DE102010044381A1 (de) | 2010-09-04 | 2012-03-08 | Merck Patent Gmbh | Farbstoff-Ascorbinsäurederivate |
WO2012065685A1 (fr) | 2010-11-19 | 2012-05-24 | Merck Patent Gmbh | Dérivés de l'acide ascorbique en tant que composants colorants d'oxydation |
EP2482159A2 (fr) | 2011-01-28 | 2012-08-01 | Honeywell International, Inc. | Procédés et systèmes reconfigurables pour optimiser la performance d'un système de maintenance basé sur des conditions |
WO2012107158A1 (fr) | 2011-02-10 | 2012-08-16 | Merck Patent Gmbh | Composés 1,3-dioxan-5-one |
DE102011010841A1 (de) | 2011-02-10 | 2012-08-16 | Merck Patent Gmbh | (1,3)-Dioxan-5-on-Verbindungen |
WO2013045016A2 (fr) | 2011-09-29 | 2013-04-04 | Merck Patent Gmbh | Oxydes de phosphane en tant qu'accélérateurs de réaction |
DE102011115285A1 (de) | 2011-09-29 | 2013-04-04 | Merck Patent Gmbh | Phosphanoxide als Reaktionsbeschleuniger |
DE102011116165A1 (de) | 2011-10-14 | 2013-04-18 | Merck Patent Gmbh | Benzodioxepin-3-on-Verbindungen |
WO2013091775A2 (fr) | 2011-12-21 | 2013-06-27 | Merck Patent Gmbh | Utilisation de dérivés du cyclohéxanol comme principes actifs antimicrobiens |
WO2013159865A1 (fr) | 2012-04-25 | 2013-10-31 | Merck Patent Gmbh | Utilisation de dérivés de dicyclohexyl-méthanol présentant des propriétés antimicrobiennes |
WO2013167220A1 (fr) | 2012-05-08 | 2013-11-14 | Merck Patent Gmbh | Utilisation de dérivés de cyclohexanol-éther à propriétés antimicrobiennes |
DE102012016191A1 (de) | 2012-08-16 | 2014-03-13 | Merck Patent Gmbh | Verwendung von Cyclohexanolethern mit antimikrobiellen Eigenschaften |
DE102012016194A1 (de) | 2012-08-16 | 2014-03-13 | Merck Patent Gmbh | Verwendung von Dicyclohexylmethanolderivaten mit antimikrobiellen Eigenschaften |
DE102012016960A1 (de) | 2012-08-28 | 2014-03-06 | Merck Patent Gmbh | Aminoester von Aminosäuren als Reaktionsbeschleuniger |
WO2014090364A1 (fr) | 2012-12-13 | 2014-06-19 | Merck Patent Gmbh | Quinones substituées ou analogues utilisés comme colorants |
WO2014127882A1 (fr) | 2013-02-25 | 2014-08-28 | Merck Patent Gmbh | Dérivés de glucuronolactone utilisés comme substances autobronzantes |
WO2016142026A1 (fr) | 2015-03-06 | 2016-09-15 | Merck Patent Gmbh | Tensioactifs fluorés situés dans des émulsions |
WO2017008877A1 (fr) | 2015-07-14 | 2017-01-19 | Merck Patent Gmbh | Compositions d'agents tensioactifs fluorés et d'antioxydants |
WO2018162368A1 (fr) | 2017-03-06 | 2018-09-13 | Merck Patent Gmbh | Utilisation de solutés compatibles |
KR20190064054A (ko) * | 2017-11-30 | 2019-06-10 | (주)아모레퍼시픽 | Low pH의 효능 물질을 포함하며 안정도가 향상된 유화 조성물 |
KR102552783B1 (ko) | 2017-11-30 | 2023-07-10 | (주)아모레퍼시픽 | Low pH의 효능 물질을 포함하며 안정도가 향상된 유화 조성물 |
WO2021018990A1 (fr) | 2019-08-01 | 2021-02-04 | Merck Patent Gmbh | Prévention et réduction des troubles de la kératinisation, et agents cosmétiques associés |
WO2025024904A1 (fr) * | 2023-07-28 | 2025-02-06 | L'oreal | Composition cosmétique, utilisation de la composition cosmétique et procédé de fabrication de la composition cosmétique |
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