EP1235552A2 - Zubereitung die organischen uv-a-filter enthalten und verfahren zur verschiebung der maximalen absorption der wellenlänge - Google Patents

Zubereitung die organischen uv-a-filter enthalten und verfahren zur verschiebung der maximalen absorption der wellenlänge

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Publication number
EP1235552A2
EP1235552A2 EP00966219A EP00966219A EP1235552A2 EP 1235552 A2 EP1235552 A2 EP 1235552A2 EP 00966219 A EP00966219 A EP 00966219A EP 00966219 A EP00966219 A EP 00966219A EP 1235552 A2 EP1235552 A2 EP 1235552A2
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European Patent Office
Prior art keywords
group
organic
groups
chosen
derivatives
Prior art date
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Application number
EP00966219A
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English (en)
French (fr)
Inventor
Sandrine Chodorowski
Francis Xavier Quinn
Clément Sanchez
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LOreal SA
Original Assignee
LOreal SA
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Publication date
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Publication of EP1235552A2 publication Critical patent/EP1235552A2/de
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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/28Zirconium; Compounds thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/11Encapsulated compositions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35Ketones, e.g. benzophenone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/16Emollients or protectives, e.g. against radiation
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00Barrier 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
    • A61Q17/04Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41Particular ingredients further characterized by their size
    • A61K2800/412Microsized, i.e. having sizes between 0.1 and 100 microns

Definitions

  • the present invention relates generally to a material obtained by the sol-gel route having a maximum absorption wavelength ( ⁇ ma ⁇ ) in the range from 370 to 400 nm, a method for shifting the wavelength d maximum absorption of a material comprising an organic UV-A sunscreen, as well as a cosmetic and / or dermatological composition including such a material.
  • UV-B radiation must therefore be filtered.
  • UV-A rays wavelengths between 320 and 400 nm, which cause browning of the skin. are likely to induce an alteration thereof, in particular in the case of sensitive skin or skin continuously exposed to solar radiation.
  • UV-A rays cause in particular a loss of elasticity in the skin and the appearance of wrinkles, leading to premature aging. They promote the initiation of the erythematous reaction or amplify this reaction in certain subjects and can even be at the origin of phototoxic or photoallergic reactions. It is therefore desirable to also filter UV-A radiation.
  • PCT WO 93/10753 and numbers WO 93/1 1135 of Slavtcheff et al disclose respectively a sunscreen metal complex type of dibenzoylmethane derivatives, whose maximum absorption wavelength ⁇ male is equal to 366 nm, and a process for preparing this new sun filter.
  • ⁇ male is equal to 366 nm
  • ⁇ female is equal to 366 nm
  • ⁇ male is equal to 366 nm
  • a process for preparing this new sun filter At present, we only know no solar UV-A suitable organic filters having a maximum absorption wavelength ( ⁇ ) greater than or equal to 370 nm with an extinction coefficient ⁇ > 25,000 mol '1 . Castor 1 , preferably ⁇ > 30,000 mol - 1 . I "1. cm " 1 .
  • Parsol® 1789 - ⁇ ma ⁇ 358 nm
  • the subject of the present invention is therefore a material capable of being obtained by the sol-gel route, comprising at least one organic UV-A solar filter of ⁇ ma 370 less than 370 nm and at least one compound of zirconia, titanium or of aluminum, the material having a maximum absorption wavelength which is in the range from 370 to 400 nm.
  • the present invention also relates to a method for moving the maximum absorption wavelength of an organic UV-A solar filter of ⁇ ma ⁇ less than 370 nm, in the range from 370 to 400 nm.
  • the present invention also relates to cosmetic and / or dermatological compositions for the photoprotection of the skin and / or keratin materials, comprising a material of the invention.
  • An object of the present invention is a material capable of being obtained by the sol-gel route which has a maximum absorption wavelength ( ⁇ ma ⁇ ) in the range from 370 to 400 nm and which comprises:
  • organic UV-A sunscreen means any organic compound absorbing UV radiation in the wavelength range 320-400 nm.
  • the metal alkoxides are chosen from the group consisting of: (1) metallo-organic compounds corresponding to one of the following formulas:
  • M and M ' represent, independently of one another, an atom of zirconia, titanium or aluminum, n and n' denote the respective valences of the metal atoms represented by M and M ',
  • Ri represents a hydrocarbon group at C j _3 0 , preferably at C, _ 6 , linear or branched, saturated or unsaturated, optionally comprising a heteroatom such as a nitrogen, sulfur, oxygen or phosphorus, and more preferably a linear or branched alkyl group, C ⁇ g, preferably C j.6 ,
  • R and R ' independently of one another, represent a C, .30 , preferably C 2.20 , linear, branched or cyclic, saturated or unsaturated hydrocarbon group, optionally comprising a heteroatom such as a d atom nitrogen, phosphorus, sulfur or oxygen, such as, for example, a linear or branched alkyl group, a cycloalkyl group or an aryl group, said groups R and R 'being able to be substituted by groups capable of reacting with the functionalized organic or silicone polymer such as, for example, halogen atoms, hydroxyl, acyl, carboxyl, ester, thiol, alkylthioalkyl, epoxy, isocyanate, thiocyanate, ureido, thio-ureido, urethane, imidazolo, morpholino groups pyrrolo, ethylenically unsaturated groups such as (meth) acrylic and vinyl groups, halogen groups such as
  • R represents a divalent C ⁇ Q hydrocarbon group, linear, branched or cyclic, saturated or unsaturated, optionally comprising a heteroatom such as a nitrogen, phosphorus, sulfur or oxygen atom, such as for example a linear or branched alkylene group, a cycloalkylene group or an arylene group, said group R "possibly being substituted by groups capable of reacting with the organic or silicone polymer such as those defined above, and which can additionally comprise a cosmetically or dermatologically active group such as those defined above; (2) complexed or chelated metallo-organic compounds corresponding to one of the following formulas:
  • X represents a monodentate ligand or a chelating group comprising a nitrogen atom, a phosphorus atom, a sulfur atom or an oxygen atom, which can be covalently linked to a group capable of reacting with said functionalized organic polymer or said functionalized silicone polymer (c) such that, for example, those defined above, and which may comprise a cosmetically or dermatologically active group such as, for example, those defined above, x represents the number of ligands X; and b represents the number of binding atoms of ligand X .
  • monodentate ligand is meant a group comprising a single atom capable of bonding with the central metallic atom.
  • chelating group is meant a polydentate ligand linked to a single central metal atom by more than one doublet donor atom.
  • Examples of such monodentate or polydentate ligands (X) that may be mentioned are sulfuric acids, sulfonic acids, phosphonic acids, phosphoric acids, carboxylic acids, ketones, ⁇ -diketones, esters, ⁇ -ketoesters, amines, ⁇ -ketoamines, amino acids preferably ⁇ - or ⁇ — hydroxylated and their derivatives, ⁇ - or ⁇ -hydroxyacids, ethers and polyethers, imines, optionally hydroxylated amides, azo compounds, thiols, ureas, thioether sulfoxides, thioether sulfones, optionally cyclic thioethers, di (thioethers), mono-alcohols or po- lyols, dextrin and its derivatives, thiazolidines.
  • diketones such as 2,4-pentanedione, 2,4-hexafluoropentanedione, 2,2,6,6-tetramethyl-3,5-heptanedione
  • salicylic acid and its derivatives such as (meth) acrylamino-4- or -5-salicylic acid
  • lactic, succinic, acetic and citric acids esters of (meth) acrylic acid such as acetoxyethyl methacrylate, methyl ⁇ -hydroxy (meth) acrylate; ethyl acetoacetate, methyl acetoacetate and acetylacetone; EDTA; low molecular weight polyethers such as poly (ethylene glycol) and poly (propylene glycol); polyethyleneimines; lysine and its derivatives such as ⁇ -N- (meth) acryloyl-L-lysine; cysteine and its derivatives such as N-acetylcy
  • the organic UV-A solar filter with a ⁇ ma ⁇ less than
  • 370 nm can be any suitable organic compound having a maximum absorption wavelength of less than 370 nm.
  • organic UV-A sunscreens which can be used according to the invention, mention may be made of: (1) dibenzoylmethane derivatives;
  • R 7 and R 9 identical or different, represent an atom of hy- drogen, a halogen atom, an OH group, a saturated or unsaturated, linear or branched C j -C 10 alkyl group, a saturated or unsaturated, linear or branched C, -C 10 alkoxy group, or an HSO3 group ;
  • R 10 represents a hydrogen atom or HSO3
  • R g represents a hydroxy group; an OR group jj where R, j represents an alkyl group, saturated or unsaturated, linear or branched C j -C lrj ; or a group with the following structure:
  • R 12 represents a hydrogen atom or HSO3; or a group of the following formula:
  • Z represents an oxygen atom or a group -NH-
  • R 13 , R 14 , R 15 and R 16 identical or different, represent a hydrogen atom, a halogen atom, an OH group, an alkyl group, saturated or unsaturated, linear or branched at C J-CJ Q ; a linear or branched C 10 -C 10 alkoxy group, saturated or not; or an HSO3 group; (3) active filters in UV-A of the benzimidazole or benzoxazole type of formula (V) below:
  • W represents an oxygen atom or a group -NH-
  • R 17 represents a hydrogen atom or HS0 3 ;
  • R 18 represents an alkoxy group, linear or branched, comprising from 1 to 10 carbon atoms approximately or a group of the following formula:
  • Y represents an oxygen atom or a group -NH-
  • R 19 represents a hydrogen atom or HSO 3 ; (4) benzophenone derivatives such as those of formula (VI) below
  • R 20 represents a hydrogen atom or an alkyl group, saturated or not, linear or branched in CJ-CJ;
  • R 1 and R 22 identical or different, represent a hydrogen atom, a halogen atom, an OH group, an alkyl group, saturated or unsaturated, linear or branched C j -C 10; an alkoxy group, saturated or not, li- born or branched in C, -C 10 or an HSO 3 group;
  • R 23 represents a hydrogen atom, OH, an alkyl group, saturated or not, linear or branched in C j -C 10 or an alkoxy group, saturated or not, linear or branched in CC 10 ;
  • R 24 represents OH, a hydrogen atom or an alkyl group, saturated or not, linear or branched C j -C 10 ;
  • silane derivatives or polyorganosiloxanes containing benzophenone group such as those described in documents EP-A-0 389 377, FR-A-2 657 351 and EP-A-0 655 453; (6) anthranilates; and
  • dibenzoylmethane derivatives which are particularly suitable in the context of the present invention, there may be mentioned, in particular without limitation: 2-methyldibenzoylmethane, 4-methyldibenzoylmethane, 4-isopropyldibenzoylmethane, 4-tert-butyldibenzoylmethane, 2 , 4-dimethyldibenzoylmethane, 2,5-dimethyldibenzoylmethane, 4,4'-diisopropyldibenzoylmethane, 4,4'-dimethoxydibenzoylmethane, 4-tert-butyl-4'-methoxydibenzoylmethane, 2-methyl-5-isopropyl '-methoxydibenzoylmethane, 2-methyl-5-tert-butyl-4'-methoxydibenzoylmethane, 2,4-dimethyl-4'-methoxydibenzoylme
  • Another preferred dibenzoylmethane derivative according to the present invention is 4-isopropyldibenzoylmethane, sold under the name of "EUSOLEX® 8020" by the company MERCK, and corresponding to the following structural formula:
  • a particularly preferred compound of formula (IV) is benzene-1,4- [di (3-methylidenecampho-10-sulfonic acid)] such as the product sold under the name MEXORYL® SX by the company CHIMEX.
  • Benzene-1, 4- [di (3-methylidenecamphosulfonic acid)] and its various salts (compound D), described in particular in patent applications FR-A-2 528 420 and FR-A-2 639,347, are filters already known per se (so-called broadband filters) capable of absorbing ultraviolet rays of wavelength ranging from 280 nm to 400 nm, with absorption maxima of between 320 and 370 nm, especially around 345 nm. These filters have the following general formula:
  • D represents a hydrogen atom, an alkali metal or core an NH (R 25 ) 3 + group in which the R 25 groups which may be identical or different, represent a hydrogen atom, a CC 4 alkyl or hydroxyalkyl group or else a group M n + / n, M n + representing a polyvalent metal cation in which n is equal to 2 or 3 or 4, M " " " 1 " preferably representing a metal cation chosen from Ca 2+ ,
  • benzophenone derivatives of formula (VI) there may be mentioned more particularly those chosen from the group consisting of:
  • benzophenone-1 2,4-dihydroxybenzophenone
  • UVINUL® 400 the product sold under the name UVINUL® 400 by BASF
  • benzophenone-2 such as the product sold under the name UVINUL® D50 by BASF;
  • UVINUL® MS40 by BASF; as well as its sodium sulfonate form (benzophenone-5);
  • benzophenone-6 2,2'-dihydroxy-4,4'-dimethoxybenzophenone
  • HELISORB® 1 1 by NORQUAY
  • benzophenone-7 5-chloro-2-hydroxybenzophenone
  • the present invention include in particular menthyl anthranilate as the product sold under the name Neo Heliopan MA ® by Haarmann & Reimer.
  • the functionalized organic or silicone polymer of the material according to the invention may be a random, block and / or grafted homopolymer or copolymer chosen from:
  • polyethers such as homopolymers and copolymers of methylene oxide, ethylene oxide, propylene oxide or tetramethylene oxide;
  • polyorganosiloxanes such as polydimethylsiloxanes, poly-methylphenylsiloxanes, polyphenylsiloxanes, polyorganosiloxanes substituted on the chain or at the chain end with amino acid groups, polyoxyethylene chains, amino or polyamino groups, hydroxy groups, carboxylic acid groups, alkyl chains, vinyl or acrylic grafts or sequences, fluorinated or perfluorinated grafts or sequences; (n) polyorganophosphazenes;
  • hydrocarbon homopolymers and copolymers as mentioned above can be block and / or grafted by polysiloxane chains.
  • organic or silicone polymers can also contain a cosmetically or dermatologically active group such as those listed above.
  • organic or silicone polymers are not functionalized, they can be either by reaction within the composition itself, such as, for example, in the case of polyorganosiloxanes, or by prior reaction by the usual methods before formation. of composition.
  • organic or silicone polymers preferred according to the invention, mention may especially be made of poly (2-ethyl-2-oxazoline).
  • polydimethylsiloxane-diols a terpolymer of vinyl acetate, vinyl 4-tert-butylbenzoate and crotonic acid (65/25/10), polydimethylsiloxane-diols, polyethylene glycols, poly (vinyl alcohol and poly (pyrrolidone) The most preferred are the polydimethylsiloxane diols.
  • the material according to the invention contains a precursor of the organic or silicone polymer, it is essentially one or more monomers capable of leading to an organic or silicone polymer functionalized by polymerization of unsaturated double bonds or by polycondensation during l application of the composition.
  • the polymerization can be initiated conventionally thermally in the presence of conventional free radical initiators, by irradiation with UV radiation, by electron beams by ionic pathway (cationic or anionic) or by any known polymerization technique.
  • the solvent used in the material of the present invention is preferably a lower, linear or branched alcohol, better still ethanol.
  • the generally used quantities of the various components of the material are the following, expressed relative to the total weight of the material:
  • Another object of the present invention relates to a method for moving in the range from 370 to 400 nm, the maximum absorption wavelength ( ⁇ ma ⁇ ) of an organic UV-A filter having a ⁇ ma ⁇ less than 370 nm, which consists in combining with said filter a sol comprising at least one functionalized organic polymer or a precursor of this polymer, or at least one functionalized silicone polymer or a precursor of this polymer, at least one metal alkoxide chosen from zirconium, titanium and aluminum alkoxides, at least one solvent, and a quantity of water sufficient for the partial and / or total hydrolysis of the metal alkoxide and its condensation. All components are as defined above.
  • the metal alkoxide is mixed with a polymer solution before the addition of the filter.
  • a further object of the present invention is a cosmetic and / or dermatological composition, comprising, in a cosmetically and / or dermatologically acceptable carrier, a material according to the present invention, as defined above.
  • This cosmetic and / or dermatological composition comprises the material according to the invention, in an effective amount ranging from 1% by weight to 99% by weight, preferably from 5% by weight to 60% by weight, by relative to the total weight of the composition.
  • the material according to the invention is dried and ground and added in the form of particles in the composition.
  • the average size of the particles obtained after drying and grinding is in the range from 0.1 ⁇ m to 50 ⁇ m, preferably from 0.1 ⁇ m to 20 ⁇ m, and better still from 0.1 ⁇ m to 10 ⁇ m.
  • the cosmetic and / or dermatological compositions targeted by the present invention can of course contain one or more complementary sunscreens, water-soluble, liposoluble or insoluble in the cosmetic solvents commonly used, different from the organic UV-A solar filters defined above.
  • additional filters can be chosen in particular from cinnamic acid derivatives, salicylic derivatives, camphor derivatives other than those corresponding to formula (IV), triazine derivatives such as those described in US patent applications.
  • complementary active sunscreens mention may be made of: - p-aminobenzoic acid,
  • the cosmetic and / or dermatological compositions according to the invention may also contain agents for tanning and / or artificial browning of the skin (self-tanning agents) such as, for example, dihydroxyacetone (DHA).
  • the cosmetic and / or dermatological compositions according to the vention may also contain pigments or else nanopigments (average size of the primary particles: generally between 5 nm and 100 nm, preferably between 10 and 50 nm) of metallic oxides coated or not, such as, for example, nanopigments titanium oxide (amorphous or crystallized in rutile form and / or anatase) of iron, zinc, zirconium or cerium which are all well-known photoprotective agents acting by physical blocking (reflection and or diffusion) UV radiation.
  • Conventional coating agents are moreover alumina and / or aluminum stearate.
  • Such coated or uncoated metallic oxide nanopigments are in particular described in patent applications EP-A-0 518 772 and EP-A-0 518 773.
  • the cosmetic and / or dermatological compositions in accordance with the present invention may also comprise conventional cosmetic adjuvants, in particular chosen from fatty substances, organic solvents, ionic or nonionic thickeners, softeners, antioxidants, anti agents -free radicals, opacifiers, stabilizers, emollients, silicones, ⁇ -hydroxy acids, anti-foaming agents, hydrating agents, vitamins, perfumes, preservatives, surfactants, fillers, sequestrants, polymers, propellants, basifying or acidifying agents, dyes or any other ingredient usually used in the cosmetic and / or dermatological field, in particular for the manufacture of sunscreen compositions in the form of emulsions.
  • conventional cosmetic adjuvants in particular chosen from fatty substances, organic solvents, ionic or nonionic thickeners, softeners, antioxidants, anti agents -free radicals, opacifiers, stabilizers, emollients, silicones, ⁇ -hydroxy acids, anti-fo
  • the fatty substances can consist of an oil or a wax or their mixtures.
  • oil is meant a compound which is liquid at room temperature.
  • wax is intended to mean a compound which is solid or substantially solid at room temperature, and the melting point of which is generally greater than 35 ° C.
  • oils mention may be made of mineral oils (petrolatum); vegetable (sweet almond oil, macadamia oil, blackcurrant seed, jojoba); synthetics such as perhydrosqualene, alcohols, fatty acids or esters (such as the benzoate of C 12 -C 15 alcohols sold under the name "Finsolv TN" by the company Finetex, octyl palmitate, lanolate isopropyl, triglycerides including those of capric / caprylic acids), ethoxylated or propoxylated fatty esters and ethers; silicone (cyclomethicone, preferably with 4 or 5 silicon atoms, polydimethylsiloxane) or fluorinated, polyalkylenes.
  • mineral oils petrolatum
  • vegetable sweet almond oil, macadamia oil, blackcurrant seed, jojoba
  • synthetics such as perhydrosqualene, alcohols, fatty acids or esters (such as the benzoate of C 12
  • waxy compounds there may be mentioned paraffin, carnauba wax, beeswax, hydrogenated castor oil.
  • organic solvents mention may be made of lower alcohols and polyols.
  • the thickeners can be chosen in particular from crosslinked polyacrylic acids, guar gums and modified or unmodified celluloses such as hydroxypropylated guar gum, methylhydroxyethylcellulose, hydroxypropylmethylcellulose and silicone gums such as, for example, a derivative of polydimethylsiloxane.
  • compositions according to the invention can be prepared according to techniques well known to those skilled in the art, in particular those intended for the preparation of emulsions of oil-in-water type or water-in-1'chel.
  • This cosmetic and / or dermatological composition can be in particular in the form of an emulsion, simple or complex (O / W. W / O, O / W / O or W / O / W) such as a cream, a milk , or in the form of a gel or a cream gel, powder, solid stick and optionally be packaged as an aerosol and be in the form of foam or spray.
  • an emulsion, simple or complex O / W. W / O, O / W / O or W / O / W
  • a cream, a milk or in the form of a gel or a cream gel, powder, solid stick and optionally be packaged as an aerosol and be in the form of foam or spray.
  • the cosmetic and or dermatological compositions according to the invention are in the form of an oil-in-water emulsion.
  • the aqueous phase thereof may comprise a nonionic vesicular dispersion prepared according to known methods (Bangham, Standish and Watkins, J. Mol. Biol. 13, 238 (1965), FR 2 315 991 e FR 2 416 008).
  • the cosmetic and / or dermatological composition according to the invention is used as a protective composition for the skin or keratin materials, against ultraviolet rays, as a sunscreen composition or as a make-up product.
  • the cosmetic composition according to the invention when used for protecting the hair, it can be in the form of shampoo, lotion, gel, emulsion, nonionic vesicular dispersion, and can constitute, for example, a composition to rinse off, to apply before or after shampooing, before or after coloring or bleaching, before, during or after perming or straightening, a styling or treating lotion or gel, a lotion or gel for brushing or setting, a composition of perm or hair straightening, coloring or bleaching.
  • a composition to rinse off to apply before or after shampooing, before or after coloring or bleaching, before, during or after perming or straightening, a styling or treating lotion or gel, a lotion or gel for brushing or setting, a composition of perm or hair straightening, coloring or bleaching.
  • the aqueous phase (comprising in particular hydrophilic filters) generally represents from 50 to 95% by weight, preferably from 70 to 90% by weight, relative to the entire formulation
  • the oily phase (comprising in particular lipophilic filters), from 5 to 50% by weight, preferably from 10 to 30% by weight, relative to the entire formulation
  • the (co) emulsifier (s) from 0.5 to 20% by weight, preferably from 2 to 10% by weight, relative to the whole of the formulation.
  • a material according to the invention is prepared from:
  • the new material is deposited on a glass plate (microscope slide).
  • a film is formed on the plate after evaporation of the volatile components of the mixture.
  • the film drying time is fast, that is to say between 1 and 3 minutes.
  • the absorption band of the new material is evaluated by UV-vis absorption spectrometry.
  • the value of ⁇ j , ⁇ moved to 378 nm compared to the ⁇ ma ⁇ of 358 nm of PARSOL® 1789 before the preparation of the material.
  • the effectiveness of the new material is not significantly reduced.
  • This new material is film-forming, completely remanent with water and ethanol, and does not release under these conditions and in polar and non-polar cosmetic oils.
  • a material according to the invention is prepared from:
  • titanium tetraisopropoxide from the company Fluka, Parsol ®
  • a material according to the invention is prepared from
  • Parsol® 1789 dissolved in THF is added, with stirring for 20 minutes, then the PDMS-diol is added. The mixture is left stirring at room temperature for 60 minutes. The new material is then ready for use.

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EP00966219A 1999-10-01 2000-09-28 Zubereitung die organischen uv-a-filter enthalten und verfahren zur verschiebung der maximalen absorption der wellenlänge Withdrawn EP1235552A2 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9912321 1999-10-01
FR9912321A FR2799120B1 (fr) 1999-10-01 1999-10-01 Materiau comprenant un filtre uv-a organique et procede de deplacement de la longueur d'onde d'absorption maximale
PCT/FR2000/002687 WO2001024768A2 (fr) 1999-10-01 2000-09-28 Materiau comprenant un filtre uv-a organique et procede de deplacement de la longueur d'onde d'absorption maximale

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EP1235552A2 true EP1235552A2 (de) 2002-09-04

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EP00966219A Withdrawn EP1235552A2 (de) 1999-10-01 2000-09-28 Zubereitung die organischen uv-a-filter enthalten und verfahren zur verschiebung der maximalen absorption der wellenlänge

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EP (1) EP1235552A2 (de)
JP (1) JP2003510342A (de)
KR (1) KR20010080582A (de)
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CN101484538A (zh) * 2006-01-18 2009-07-15 斯帕克西斯公司 新型单体材料和聚合材料
CN102552064B (zh) * 2011-12-26 2015-03-18 上海应用技术学院 包覆对氨基苯甲酸或其衍生物的酯类所形成的化学防晒剂的聚硅氧烷复合粒子及制备方法
CN102552068B (zh) * 2011-12-26 2016-01-20 上海应用技术学院 一种包覆水杨酸或其衍生物的酯类所形成的化学防晒剂的聚硅氧烷复合粒子及其制备方法
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CZ20011809A3 (cs) 2001-10-17
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HUP0300234A2 (hu) 2003-08-28
AU759357B2 (en) 2003-04-10
FR2799120A1 (fr) 2001-04-06
KR20010080582A (ko) 2001-08-22
ZA200104121B (en) 2002-05-03
WO2001024768A2 (fr) 2001-04-12
JP2003510342A (ja) 2003-03-18
CA2353709A1 (fr) 2001-04-12
AU7668300A (en) 2001-05-10
FR2799120B1 (fr) 2001-11-30
WO2001024768A3 (fr) 2002-07-11
PL347767A1 (en) 2002-04-22
RU2212881C2 (ru) 2003-09-27

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