EP2282713A2 - Vecteur mésoporeux contenant au moins un filtre uv organique - Google Patents

Vecteur mésoporeux contenant au moins un filtre uv organique

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Publication number
EP2282713A2
EP2282713A2 EP09745845A EP09745845A EP2282713A2 EP 2282713 A2 EP2282713 A2 EP 2282713A2 EP 09745845 A EP09745845 A EP 09745845A EP 09745845 A EP09745845 A EP 09745845A EP 2282713 A2 EP2282713 A2 EP 2282713A2
Authority
EP
European Patent Office
Prior art keywords
filter
derivatives
weight
surfactant
mesoporous
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP09745845A
Other languages
German (de)
English (en)
Inventor
Philippe Guarilloff
Bénédicte LEBEAU
Joël Patarin
Raphaël BONGUR
Claire Marichal-Westrich
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Centre National de la Recherche Scientifique CNRS
Chanel Parfums Beaute SAS
Original Assignee
Centre National de la Recherche Scientifique CNRS
Chanel Parfums Beaute SAS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Centre National de la Recherche Scientifique CNRS, Chanel Parfums Beaute SAS filed Critical Centre National de la Recherche Scientifique CNRS
Publication of EP2282713A2 publication Critical patent/EP2282713A2/fr
Withdrawn legal-status Critical Current

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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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/11—Encapsulated compositions
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/25—Silicon; Compounds thereof
    • 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
    • A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585—Organosilicon compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/56—Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms

Definitions

  • the present invention relates to a method for the preparation of a mesoporous vector containing at least one organic UV filter, as well as the vector thus obtained, the cosmetic compositions containing them and uses thereof.
  • organic UV filters have a tendency to degrade in the presence of UVA and consequently to produce free radicals which are harmful to the skin, as is the case for certain dibenzoylmethane derivatives.
  • Other organic sun filters, bearing sulphonic acid functions have a tendency to break the viscosity of gels obtained from acrylic polymers and are poorly compatible with the aqueous-phase gelling agents used in a standard fashion in sun-protection or skincare compositions. It is therefore understood that the encapsulation of these organic filters would make it possible to avoid these phenomena.
  • their inclusion in vector systems of a sufficient size to allow them to stay on the surface of the skin would also have a significant advantage from the safety point of view.
  • the stability of the encapsulation should be able to lead to a loss of less than 10% by weight, or even of less than 1% by weight, of the encapsulated compound after storing the vector system for 2 months at 45 0 C in a UV filter solvent.
  • These vector systems are capable of being obtained by mixing a silica precursor with a micellar solution of a surfactant and the UV filter (s) to be encapsulated, followed by the condensation of the silica precursor in order to form mesoporous vectors.
  • a subject of the present invention is therefore a method for the preparation of a mesoporous vector containing at least one organic UV filter, comprising the following stages:
  • micellar solution of at least one surfactant in a solvent with said organic UV filter and a silica precursor, in basic medium
  • a subject is also the mesoporous vector capable of being obtained according to this method.
  • loaded mesoporous vector denotes the mesoporous vector obtained according to the method described above, encapsulating the organic UV filter.
  • the first stage of the method according to the invention comprises the formation of a micellar solution of at least one surfactant in a solvent.
  • Micelles are aggregates formed spontaneously by surfactants when they are present in a concentration greater than their critical micellar concentration (CMC) .
  • CMC critical micellar concentration
  • the surfactants can be chosen from the anionic, non- ionic or cationic surfactants, including the amphiphilic block polymers, or mixtures thereof, the cationic surfactants being preferred for a use in the present invention.
  • the surfactants can in particular be chosen from those mentioned in the work "Emulsifiers and Detergents" by McCUTCHEON.
  • cationic surfactants include the quaternary ammonium salts of formula (I) :
  • the Ri to R 4 radicals which can be identical or different, represent a linear or branched aliphatic radical comprising 1 to 30 carbon atoms, or an aromatic radical such as aryl or alkylaryl.
  • the aliphatic radicals can comprise heteroatoms such as in particular oxygen, nitrogen, sulphur, halogens.
  • the aliphatic radicals are for example chosen from the alkyl, alkoxy, (C2- C ⁇ ) polyoxyalkylene, alkylamide, (C12-C22) alkylamido (C2- C ⁇ Jalkyl, (C12-C22) alkyl acetate, hydroxyalkyl radicals, comprising 1 to 30 carbon atoms;
  • - X is an anion chosen from the group of the halides, phosphates, acetates, lactates, (C2- Ce) alkylsulphates, alkyl- or alkylarylsulphonates .
  • R 5 represents an alkenyl or alkyl radical comprising 8 to 30 carbon atoms for example derived from the fatty acids of tallow
  • R 6 represents a hydrogen atom, a Ci-C 4 alkyl radical or an alkenyl or alkyl radical comprising 8 to 30 carbon atoms
  • R 7 represents a Ci-C 4 alkyl radical
  • R 8 represents a hydrogen atom or a Ci-C 4 alkyl radical
  • X is an anion chosen from the group of the halides, phosphates, acetates, lactates, alkylsulphates, alkyl- or alkylarylsulphonates.
  • R 5 and R 6 denote a mixture of alkenyl or alkyl radicals comprising 12 to 21 carbon atoms for example derivatives of the fatty acids of tallow, R 7 denotes methyl, R 8 denotes hydrogen.
  • R 7 denotes methyl
  • R 8 denotes hydrogen.
  • Such a product is for example marketed under the name REWOQUAT W 75 by REWO.
  • Other examples of cationic surfactants are the quaternary diammonium salts of formula (III) :
  • R 9 denotes an aliphatic radical comprising approximately 16 to 30 carbon atoms
  • Ri 0 , Rn, R12, R13 and Ri 4 identical or different are chosen from hydrogen or an alkyl radical comprising 1 to 4 carbon atoms
  • X is an anion chosen from the group of the halides, acetates, phosphates, nitrates and methylsulphates .
  • Such quaternary diammonium salts comprise in particular diammonium propane tallow dichloride.
  • Further examples of cationic surfactants are the quaternary ammonium salts containing at least one ester function.
  • quaternary ammonium salts containing at least one ester function which can be used according to the invention are for example those of formula (IV) below:
  • Ri5 is chosen from the C 1 -C 6 alkyl radicals and the C 1 -C 6 hydroxyalkyl or dihydroxyalkyl radicals; Ri6 is chosen from: the R19-CO- radical, - the saturated or unsaturated, linear or branched
  • R 1 8 is chosen from: - the R 2I -CO- radical, - the saturated or unsaturated, linear or branched
  • Ri 7 , Ri 9 and R 2 i are chosen from the saturated or unsaturated, linear or branched C 7 - C 21 hydrocarbon radicals; n, p and r, identical or different, are integers from 2 to 6; y is an integer from 1 to 10; x and z, identical or different, are integers from 0 to 10;
  • X is an organic or inorganic, simple or complex anion; provided that the sum x + y + z equals 1 to 15, that when x equals 0 then R 16 denotes R20 and that when z equals 0 then R 1 S denotes R22 •
  • the alkyl radicals R 15 can be linear or branched and more particularly linear.
  • R 15 denotes a methyl, ethyl, hydroxyethyl or dihydroxypropyl radical and more particularly a methyl or ethyl radical.
  • the sum x + y + z equals 1 to 10.
  • R 16 is a hydrocarbon radical, it can be long and have 12 to 22 carbon atoms or short and have 1 to 3 carbon atoms .
  • R 18 is a hydrocarbon radical, it preferably has 1 to 3 carbon atoms.
  • R 17 , R 19 and R 21 are chosen from the saturated or unsaturated, linear or branched, C 11 -C 21 hydrocarbon radicals, and more particularly from the saturated or unsaturated, linear or branched C 11 -C 21 alkyl and alkenyl radicals.
  • x and z identical or different, equal 0 or 1.
  • y is equal to 1.
  • n, p and r identical or different, equal 2 or 3 and still more particularly are equal to 2.
  • the anion is preferably a halide (chloride, bromide or iodide) or an alkylsulphate, more particularly methylsulphate . It is however possible to use methanesulphonate, phosphate, nitrate, tosylate, an anion derived from organic acid such as acetate or lactate or any other anion compatible with the ammonium with an ester function.
  • the anion X " is still more particularly chloride or methylsulphate.
  • ammonium salts of formula (IV) are more particularly used, in which:
  • Ri5 denotes a methyl or ethyl radical; x and y are equal to 1 ; z is equal to 0 or 1; n, p and r are equal to 2 ; Ri6 is chosen from: the Ri 9 -CO- radical, the methyl, ethyl or C14-C22 hydrocarbon radicals, the hydrogen atom; R18 is chosen from: - the R 2I -CO- radical, the hydrogen atom;
  • Ri 7 , Ri 9 and R 2 i are chosen from the saturated or unsaturated, linear or branched C 13 -C 17 hydrocarbon radicals, and preferably from the saturated or unsaturated, linear or branched Ci 3 -Ci 7 alkyl and alkenyl radicals.
  • the hydrocarbon radicals are linear.
  • acyl radicals preferably have 14 to 18 carbon atoms and originate more particularly from a vegetable oil such as palm or sunflower oil.
  • the compound contains several acyl radicals, the latter can be identical or different.
  • Such compounds are for example marketed under the names DEHYQUART by HENKEL, STEPANQUAT by STEPAN, NOXAMIUM by CECA, REWOQUAT WE 18 by REWOWITCO.
  • the tetraalkylammonium chlorides such as for example dialkyldimethylammonium or alkyltrimethylammonium chlorides are preferred, in which the alkyl radical comprises 8 to 22 carbon atoms, in particular behenyltrimethylammonium, distearyldimethylammonium, cetyltrimethylammonium, benzyl dimethyl stearyl ammonium chlorides or also, on the other hand, stearamidopropyldimethyl (myristyl acetate) ammonium chloride marketed in particular under the name CERAPHYL 70 by VAN DYK.
  • alkyltrimethylammonium chlorides and bromides the alkyl chain of which contains 12 to 16 carbon atoms, such as hexadecyltrimethylammonium and dodecyltrimethylammonium chlorides and bromides, are the quaternary ammonium salts which are more particularly preferred according to the invention, in the case of hydrophilic organic UV filters, to the extent that they make it possible to reach a higher encapsulation level of these molecules.
  • alkyltrimethylammonium chlorides and bromides the alkyl chain of which contains 8 to 16, preferably 12 to 16 carbon atoms.
  • the solvent used in the formation of the micellar solution can be water or an oil. It is preferably water.
  • micellar solution is mixed with at least one organic UV filter intended to be encapsulated in the mesoporous vectors according to the invention.
  • the organic UV filter utilized according to the invention can be of a hydrophilic or hydrophobic nature. According to its polarity, it will rather be oriented towards the polar heads of the surfactant molecules or towards the interior of the micelles, in the first stage of the method according to the invention.
  • lipophilic or hydrophobic UV organic filters are in particular chosen from the anthranilates; cinnamic derivatives; dibenzoylmethane derivatives; salicylic derivatives, camphor derivatives; triazine derivatives such as those described in the patent applications US 4 367 390, EP 863 145, EP 517 104, EP 570 838, EP 796 851, EP 775 698, EP 878 469, EP 933 376, EP
  • hydrophobic organic filters there can be mentioned those designated below by their INCI name :
  • Ethyl PABA Ethyl Dihydroxypropyl PABA
  • Ethylhexyl Dimethyl PABA sold in particular under the name "ESCALOL 507" by ISP
  • Methoxydibenzoylmethane sold in particular under the trade name "PARSOL 1789" by SYMRISE, Isopropyl Dibenzoylmethane,
  • Octocrylene sold in particular under the trade name "UVINUL N539" by
  • - Benzylidene camphor derivatives 3-Benzylidene camphor, Methylbenzylidene camphor sold under the name "EUSOLEX 6300" by MERCK, Polyacrylamidomethyl Benzylidene camphor, - Triazine derivatives: Bis-Ethylhexyloxyphenol
  • Phenyl benzotriazole derivatives Drometrizole Trisiloxane sold under the name "Silatrizole” by RHODIA CHIMIE, Methylene bis-Benzotriazolyl Tetramethylbutyl- phenol, sold in solid form under the trade name "MIXXIM BB/100” by FAIRMOUNT CHEMICAL or in micronized form in aqueous dispersion under the trade name "TINOSORB M” by CIBA SPECIALTY CHEMICALS, - Anthranilic derivatives: Menthyl anthranilate sold under the trade name "NEO HELIOPAN MA" by DSM,
  • Imidazoline derivatives Ethylhexyl Dimethoxybenzylidene Dioxoimidazoline Propionate
  • Benzalmalonate derivatives Polyorganosiloxanes with a benzalmalonate function such as the Polysilicone- 15 sold under the trade name "PARSOL SLX" by SYMRISE,
  • the preferential hydrophobic organic UV filters are chosen from: Ethylhexyl Salicylate, Homosalate, Ethylhexyl Methoxycinnamate, Butyl Methoxydibenzoyl- methane, Octocrylene, Benzophenone-3, n-hexyl 2- (4- diethylamino-2-hydroxybenzoyl) -benzoate, 4-Methyl- benzylidene camphor, Bis-Ethylhexyloxyphenol Methoxy- phenyl Triazine, Ethylhexyl triazone, Diethylhexyl Butamido Triazone, Methylene bis-Benzotriazolyl Tetramethylbutylphenol, Drometrizole Trisiloxane, Polysilicone-15, 1, 1-dicarboxy (2, 2 ' -dimethyl-propyl) - 4, 4-diphenylbutadiene, 2,4-bis-[5- (d
  • hydrophilic organic UV filters which can be used according to the invention, there can be mentioned those referred to above under their INCI name:
  • PABA p-aminobenzoic
  • benzophenone derivatives comprising at least one sulphonic radical such as Benzophenone-4 sold under the trade name "UVINUL MS40" by BASF, Benzophenone-5 and Benzophenone-9 ;
  • benzylidene camphor derivatives comprising at least one sulphonic radical such as for example: Benzylidene Camphor Sulphonic Acid, Camphor Benzalkonium Methosulphate and Terephthalylidene Dicamphor Sulphonic Acid;
  • benzimidazole derivatives comprising at least one sulphonic radical such as for example: Phenylbenzimidazole Sulphonic Acid sold in particular under the trade name "EUSOLEX 232" by MERCK or "PARSOL HS” by GIVAUDAN, bis-benzoazolyl derivatives as described in the patents EP 669 323 and US 2,463,264 and more particularly the compound Disodium Phenyl Dibenzimidazole Tetra-sulphonate sold under the trade name "NEO HELIOPAN AP" by DSM;
  • hydrophilic cinnamate derivatives such as for example DEA Methoxycinnamate
  • hydrophilic filters the most preferential are chosen from Terephthalylidene Dicamphor
  • a silica precursor is moreover mixed with the organic UV filter and the micellar solution of surfactant.
  • This silica precursor is advantageously sodium silicate.
  • it may be hydrophobic or fumed silica such as that marketed under the trade name Aerosil ® by DEGUSSA or under the trade name Cab-O-Sil ® by CABOT, or a colloidal silica such as that marketed by GRACE under the trade name Ludox ® .
  • it may be a tetraalkyl orthosilicate such as tetraethyl orthosilicate (TEOS) or tetramethyl orthosilicate (TMOS), or or silicic acid Si(OH) 4 .
  • TEOS tetraethyl orthosilicate
  • TMOS tetramethyl orthosilicate
  • the encapsulation of the UV filter in the surfactant micelles may be improved, in certain cases, by the use of ultrasonics .
  • the mixing of the constituents described previously is carried out in a basic medium, advantageously at a pH of at least 8, which can be adjusted by the addition of a strong base such as sodium hydroxide.
  • This mixture does not generally contain ethanol as solvent, nor lecithin as surfactant .
  • the condensation of the silica precursor can then be carried out, by optional hydrolysis of the alkoxylated silicates and polycondensation of the silicic species at the interface of the surfactant micelles, for example by adjustment of the pH to an acid pH in the case of sodium silicate or to a basic pH, in the case of TEOS.
  • the organic UV filter advantageously represents at least 30% by weight, preferably at least 35% by weight, more preferentially at least 40% by weight, or even at least 50% by weight, with respect to the weight of the loaded mesoporous vector.
  • Measurement of the encapsulation level can in particular be carried out by X-ray fluorescence or by a thermogravimetric analysis (making it possible to access the total level of encapsulated molecule + surfactant) coupled with a CHN assay (oxidation then assay of CO 2 , NO 2 and H 2 O) or X-ray fluorescence or mass spectrometry analysis.
  • these encapsulation levels can be achieved according to the invention without it being necessary to mix with one of the reagents, in the first stage of the method, a co-solvent such as an alcohol which would be capable of affecting the odour of the loaded vectors obtained and/or of interacting with the support to which these vectors are intended to be applied, for example drying the skin in the case of a cosmetic application.
  • a co-solvent such as an alcohol which would be capable of affecting the odour of the loaded vectors obtained and/or of interacting with the support to which these vectors are intended to be applied, for example drying the skin in the case of a cosmetic application.
  • the weight ratio of the surfactant to the mixture of the surfactant, the silica precursor and the molecule to be encapsulated should preferentially be greater than 25% by weight, more preferentially at least 30% by weight, advantageously comprised between 30 and 50% by weight, for instance between 35 and 45% by weight inclusive.
  • the weight ratio of the silica precursor to the three abovementioned constituents is preferable for the weight ratio of the silica precursor to the three abovementioned constituents to be comprised between 15 and 35% by weight, for instance between 15 and 25% by weight or between 25 and 30% by weight inclusive, and for the weight ratio of the molecule to be encapsulated to the three abovementioned constituents to be comprised between 30 and 60% by weight, for instance between 40 and 50% by weight inclusive.
  • the weight ratio of the silica precursor to the mixture of the surfactant, the silica precursor and the molecule to be encapsulated is preferably at least 30% by weight, advantageously 30 to 60% by weight, or better, 35 to 45% by weight.
  • the weight ratio of the surfactant to the three abovementioned constituents is preferably comprised between 15 and 25% by weight inclusive, more preferentially between 15 and 20% by weight.
  • the weight ratio of the lipophilic molecule to the total of the three abovementioned constituents is for its part advantageously comprised between 35 and 50% by weight, better, between 40 and 50% by weight inclusive.
  • the UV filter is trapped in a sufficiently stable manner within the mesoporous vector for the rate of release of this UV filter in a composition containing one of its solvents to be less than 10% by weight, preferably less than 5% by weight, or better, less than 1% by weight, with respect to the weight of molecule utilized, after 2 months at 45 0 C.
  • the solvent used for carrying out this release test can be any appropriate lipophilic organic solvent, in the case where the UV filter is lipophilic, such as a paraffin oil and/or a silicone oil, or any appropriate hydrophilic organic solvent in the case where the trapped UV filter is hydrophilic, such as water.
  • the inventors have discovered that the release of the UV filter (especially the hydrophilic UV filter) in such a solvent could be reduced by adjusting the molar amounts of the surfactant and the UV filter used, so as to keep the molar ratio of the surfactant to the UV filter between 1 and 1.4 inclusive. They have also realized that using this ratio allowed to encapsulate a higher proportion of UV filter (especially hydrophilic UV filter) within the mesoporous vector of this invention.
  • the mesoporous vectors according to the invention In order to avoid their penetrating into the skin whilst being substantially undetectable in cosmetic compositions, it is preferable for the mesoporous vectors according to the invention to have an average size ranging from 200 to 500 nm. These vectors usually are in the form of agglomerates of small spheres. Their size can be adjusted by grinding in the case where their production method leads to vectors of a size greater than 500 nm. It is in any case preferable for the loaded mesoporous vectors according to the invention to have a size not exceeding 5 ⁇ m in order not to negatively affect the stability and/or the feel of the composition in which they are intended to be incorporated.
  • an additional stage of coating the mesoporous vectors formed for example using silica, alumina or a polymer such as a polyacrylate or an organopolysiloxane or by grafting functions onto their external surface, for example -Si-R' functions linked by covalent bonds to the oxygen atoms of the silica, using as an R'-SiCl3 or R'-Si(0R)3 reagent.
  • This coating stage makes it possible to obtain coated mesoporous materials which may prove to be easier to formulate or also more impervious, in certain applications.
  • the method according to the invention is preferable for the method according to the invention to be implemented continuously in a single reactor.
  • the mesoporous vectors according to the invention can be used in different types of industry, for different uses such as the protection of human skin, the protection of synthetic materials against UV and the surface treatment of plastic or metallic materials, without this list being limitative.
  • a subject of the present invention is therefore also a composition containing, in a physiologically acceptable, and preferably a cosmetically acceptable, medium at least one vector as described previously.
  • physiologically acceptable is meant compatible with the skin and optionally with its appendages such as the nails, eyelashes and hair.
  • cosmetically acceptable denotes more particularly a medium which does not produce any sensations of discomfort, such as flushing, pain, tingling or tightness, which are unacceptable to the user of cosmetic compositions .
  • composition according to the invention can also comprise at least one additive chosen from: the oils, which can be chosen in particular from: the volatile or non-volatile, linear or cyclic silicone oils, such as the polydimethylsiloxanes
  • the synthetic oils such as the fluorinated oils, the alkyl benzoates and the branched hydrocarbons such as polyisobutylene; the vegetable oils and in particular soya or jojoba; and the mineral oils such as paraffin oil; the waxes, such as ozokerite, polyethylene wax, beeswax or carnauba wax; the silicone elastomers obtained in particular by reaction, in the presence of a catalyst, of a polysiloxane having at least one reactive group (hydrogen or vinyl, in particular) and bearing at least one terminal and/or side alkyl (in particular methyl) or phenyl group, with an organosilicone such as an organohydrogenpolysiloxane; the surfactants, preferably emulsifying, whether non- ionic, anionic, cationic or amphoteric, and in particular the esters of fatty acids and polyols such as the esters of fatty acids and gly
  • composition according to the invention can also contain at least one active ingredient chosen from: agents stimulating the expression of tensin 1; agents stimulating the expression of FN3K and/or of FN3K RP; agents stimulating the expression of matriptase MT-SPl; agents stimulating the production of growth factors; anti-glycation or deglycating agents; agents increasing the synthesis of collagen or preventing its degradation (anti-collagenase agents, in particular inhibitors of matrix metalloproteinases) ; agents increasing the synthesis of elastin or preventing its degradation (anti- elastase agents); agents increasing the synthesis of glycosaminoglycans or proteoglycans or preventing their degradation (anti-proteoglycanase agents); agents stimulating the synthesis of integrins by the fibroblasts; agents increasing the proliferation or differentiation of the keratinocytes; agents increasing the proliferation of the fibroblasts; depigmenting or anti-pigmenting agents; antioxidant or anti-radical or anti-
  • a subject of the present invention is also the cosmetic use of the mesoporous vector described previously for preventing or combating cutaneous photo- ageing.
  • a subject is also the use of this mesoporous vector for the production of a composition intended to protect the skin against the effects of UV and in particular to prevent cutaneous erythema.
  • a subject is also a cosmetic method for the care and make-up of the skin, comprising the topical application to the latter of the abovementioned composition.
  • Example 1 Preparation of mesoporous vectors incorporating organic UV filters
  • Mesoporous vectors containing respectively a hydrophobic (or lipophilic) organic filter (octyl methoxycinnamate, PARSOL MCX ® marketed by GIVAUDAN) and a hydrophilic organic filter (phenylbenzimidazole sulphonic acid, PARSOL ® HS marketed by GIVAUDAN) were synthesized.
  • Example IA Encapsulation of hydrophilic UV filter
  • RBO 115 The appearance of the sample obtained (hereafter, "RBO 115"), under a scanning electron microscope, is in the form of agglomerates of between 5 and 40 ⁇ m, consisting of small spheres of a few nanometres. Its encapsulation level was approximately 27% by weight, as measured by thermogravimetry (SETARAM Labsys).
  • Thermoanalyzer under air flushing with a rise in temperature of 5°C/minute between 25 0 C and 800 0 C) coupled with X-ray fluorescence analysis (PHILIPS Magix on a pellet of 200 mg of the product mixed with 100 mg of boric acid) , whereas the theoretical amount of encapsulated UV filter expected was about 40% (starting from 30% surfactant, 40% UV filter and 30% silica) .
  • the powder obtained was grinded with a ball mill (MiniMill, PHILIPS), in the presence of three zircon balls and the speed was set at 4 for 10 minutes. A white powder having a pleasant cosmetic feel was obtained.
  • a lipophilic UV filter was encapsulated in the mesoporous vectors of this invention, using a weight ratio of silica precursor: UV filter : surfactant of about 39:45:16.
  • the appearance of the sample obtained, under an scanning electron microscope (PHILIPS XL30 FEG) is in the form of agglomerates of 5-40 ⁇ m, consisting of very of small spheres of a few nanometers.
  • Thermoanalyzer under air flushing with a rise in temperature of 5°C/minute between 25 0 C and 800 0 C) coupled with a CHN assay (ThermoElectron, Flash EA 1112) .
  • the product appeared as a white powder having a pleasant cosmetic feel.
  • Example 1C Encapsulation of hydrophilic UV filter
  • Parsol® HS was encapsulated according to this invention, following the protocol described in example 1, except that the respective amounts of reactants were changed to a weight ratio of surfactant : Parsol HS : silica of 45:35:20.
  • RBO 181 The appearance of the sample obtained (hereafter, "RBO 181"), under a scanning electron microscope, is in the form of agglomerates of between 5 and 40 ⁇ m, consisting of small spheres of a few nanometres.
  • Example 2 Evaluation of the effectiveness of the organic UV filters encapsulated in mesoporous vectors
  • a UV-visible absorption spectroscopy method was used in order to evaluate the effectiveness of encapsulated UV filters prepared as described in Example 1.
  • a light source composed of a lamp for the visible range (400-800 nm) and another for the UV ( ⁇ 400 nm) illuminated a quartz cell containing the material in the form of powder.
  • a detector picked up the reflected signal.
  • a curve illustrating the absorbance as a function of the wavelength was then drawn in the wavelength range from
  • the device used was of the PERKIN-ELMER
  • Sample 2A which corresponded to RBO115 of Example 1
  • sample 2B which was prepared in the same way as sample IB of Example 1 but starting with a silica iParsol® MCX: surfactant weight ratio of
  • Example 3 Evaluation of the stability of the encapsulation of organic UV filters in mesoporous vectors
  • Example 4 Comparison of the techniques for encapsulation of organic UV filters The stability of the different vectors incorporating organic UV filters, presented in Table 2, was compared vis-a-vis the leakage of these filters in different solvents .

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  • Cosmetics (AREA)

Abstract

La présente invention porte sur un procédé pour la préparation d'un vecteur mésoporeux contenant au moins un filtre UV organique, ainsi que sur le vecteur capable d'être ainsi obtenu. L'invention porte également sur une composition contenant ce vecteur mésoporeux dans un milieu physiologiquement acceptable et de préférence cosmétiquement acceptable, ainsi que sur un procédé cosmétique pour le soin et/ou le maquillage de la peau, comprenant l'application topique à celui-ci de cette composition. L'invention porte enfin sur l'utilisation cosmétique de ce vecteur mésoporeux pour empêcher ou combattre le photovieillissement cutané, et pour la production d'une composition destinée à protéger la peau contre les effets des ultraviolets et en particulier pour empêcher un érythème cutané.
EP09745845A 2008-05-16 2009-05-18 Vecteur mésoporeux contenant au moins un filtre uv organique Withdrawn EP2282713A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0853192A FR2931067B1 (fr) 2008-05-16 2008-05-16 Vecteur mesoporeux renfermant au moins un filtre uv organique
PCT/EP2009/056004 WO2009138513A2 (fr) 2008-05-16 2009-05-18 Vecteur mésoporeux contenant au moins un filtre uv organique

Publications (1)

Publication Number Publication Date
EP2282713A2 true EP2282713A2 (fr) 2011-02-16

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Family Applications (1)

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EP09745845A Withdrawn EP2282713A2 (fr) 2008-05-16 2009-05-18 Vecteur mésoporeux contenant au moins un filtre uv organique

Country Status (3)

Country Link
EP (1) EP2282713A2 (fr)
FR (1) FR2931067B1 (fr)
WO (1) WO2009138513A2 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3282290A1 (fr) 2016-08-09 2018-02-14 Essilor International Composition pour la fabrication d'une lentille ophtalmique comprenant un additif absorbant la lumière encapsulé
WO2019155244A1 (fr) 2018-02-09 2019-08-15 Essilor International Nanoparticules d'agent d'absorption de lumière encapsulé, préparation de ces nanoparticules, et lentille ophtalmique comprenant lesdites nanoparticules

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3193836A1 (fr) 2014-09-15 2017-07-26 PharmaSol GmbH Matériaux particulaires chargés d'agents actifs pour administration topique
US20220395440A1 (en) * 2019-10-30 2022-12-15 Dow Global Technologies Llc Sun care compositions with hollow mesoporous silica nanospheres

Family Cites Families (3)

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Publication number Priority date Publication date Assignee Title
WO1998014399A1 (fr) * 1996-09-30 1998-04-09 Shiseido Co., Ltd. Poudre d'oxyde de silicium et son procede de production, produits cosmetique fabriques a l'aide de celle-ci, poudre retenant les micelles et poudre retenant le parfum
TWI233362B (en) * 1999-03-26 2005-06-01 Shiseido Co Ltd Titanium silica complex and cosmetics formulated with the same
JP4125201B2 (ja) * 2003-08-05 2008-07-30 ロレアル 光学的活性物質を内包した多孔質粒子を含有する化粧品組成物

Non-Patent Citations (1)

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See references of WO2009138513A3 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3282290A1 (fr) 2016-08-09 2018-02-14 Essilor International Composition pour la fabrication d'une lentille ophtalmique comprenant un additif absorbant la lumière encapsulé
WO2018029249A1 (fr) 2016-08-09 2018-02-15 Essilor International Composition pour la fabrication d'une lentille ophtalmique comprenant un additif absorbant la lumière encapsulé
WO2018029540A1 (fr) 2016-08-09 2018-02-15 Essilor International Lentille ophtalmique comprenant un additif encapsulé absorbant la lumière
WO2019155244A1 (fr) 2018-02-09 2019-08-15 Essilor International Nanoparticules d'agent d'absorption de lumière encapsulé, préparation de ces nanoparticules, et lentille ophtalmique comprenant lesdites nanoparticules

Also Published As

Publication number Publication date
WO2009138513A3 (fr) 2010-11-25
WO2009138513A2 (fr) 2009-11-19
FR2931067B1 (fr) 2010-06-25
FR2931067A1 (fr) 2009-11-20

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