ZA200104121B - Material comprising an organic US-A filter and method for displacing the maximum absorption wavelength. - Google Patents

Material comprising an organic US-A filter and method for displacing the maximum absorption wavelength. Download PDF

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ZA200104121B
ZA200104121B ZA200104121A ZA200104121A ZA200104121B ZA 200104121 B ZA200104121 B ZA 200104121B ZA 200104121 A ZA200104121 A ZA 200104121A ZA 200104121 A ZA200104121 A ZA 200104121A ZA 200104121 B ZA200104121 B ZA 200104121B
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South Africa
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group
organic
chosen
groups
material according
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ZA200104121A
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Sandrine Chodorowski
Francis Xavier Quinn
Clement Sanchez
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Oreal
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    • 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
    • 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
    • A61K8/28—Zirconium; 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
    • A61K8/02—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
    • A61K8/30—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
    • A61K8/34—Alcohols
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • 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

Description

4 1] 20014324 B 99/1785 EXT (GD/IC)
MATERIAL COMPRISING AN ORGANIC UV-A SCREENING AGENT AND - PROCESS FOR SHIFTING THE MAXIMUM ABSORPTION WAVELENGTH
The present invention generally relates to a material obtained by the sol-gel route exhibiting a maximum absorption wavelength (2...) within the range from 370 to 400 nm, to a process for shifting the maximum absorption wavelength of a material comprising an organic
UV-A sunscreen agent and to a cosmetic and/or dermatological composition including such a material.
It is known that light radiation with wavelengths of between 280 nm and 400 nm makes possible browning of the human epidermis and that rays with wavelengths of between 280 nm and 320 nm, known under the name of UV-B radiation, result in erythemas and cutaneous burns which can be harmful to the development of natural tanning; this UV-B radiation therefore has to be screened out.
It is also known that UV-A rays with wavelengths of between 320 and 400 nm, which result in browning of the skin, are capable of bringing about a detrimental" change in the latter, in particular in the case of sensitive skin or of skin continually exposed to solar radiation. UV-A rays result in particular in a loss of elasticity of the skin and the appearance of wrinkles, leading to premature aging. They promote the triggering of the erythemal reaction or enhance this reaction in some subjects and can even be the cause of phototoxic or photoallergic reactions. It is therefore desirable also to screen out UV-A radiation.
The commonly used sunscreen agents do not include organic screening agents effective in the long UV-A spectral range corresponding to wavelengths ranging from 370 to 400 nm. In other words, antisun protection is not provided in this spectral range. This is all the more serious as this more penetrating radiation is partly responsible for the development of certain skin cancers and of immunosuppression, in addition to cutaneous . photoaging.
In the state of the prior art, Patent
Applications PCT numbers WO 93/10753 and WO 93/11135 of
Slavtcheff et al. respectively disclose a sunscreen agent of metal complex of dibenzoylmethane derivatives type, the maximum absorption wavelength of which is 366 nm, and a process for the preparation of this novel sunscreen agent. Currently, appropriate organic UV-A sunscreen agents exhibiting a maximum absorption wavelength (Ap) of greater than or equal to 370 nm with a coefficient of extinction ¢ > 25 000 molt.l1'.cm?, preferably g > 30 000 mol?t.1'.cm?, are unknown.
It has been found, surprisingly, that, by combining an organic UV-A screening agent having a _ maximum absorption wavelength (A...) of less than 370 nm, such as 4-tert-butyl-4'-methoxydibenzoylmethane (Parsol® 1789; Apa = 358 nm), with certain zirconium, titanium and aluminum compounds, it is possible to obtain a material for which the absorption band is shifted and which exhibits a maximum absorption wavelength within the range from 370 to 400 nm, with an ¢ value which is not significantly reduced.
A subject matter of the present invention is therefore a material capable of being obtained by the sol-gel route comprising at least one organic UV-A sunscreen agent with a A, of less than 370 nm and at least one zirconium, titanium or aluminum compound, the material having a maximum absorption wavelength which is situated in the range from 370 to 400 nm.
The present invention also relates to a process for shifting the maximum absorption wavelength of an organic UV-A sunscreen agent with a A,,, of less than 370 nm into the range from 370 to 400 nm.
A further subject matter of the present invention is cosmetic and/or dermatological compositions for the photoprotection of the skin and/or keratinous substances . comprising a material of the invention.
Other characteristics, aspects and advantages of the invention will become more clearly apparent on reading the description and examples which follow.
A subject matter of the present invention is a material capable of being obtained by the sol-gel route which exhibits a maximum absorption wavelength (A,,.) within the range from 370 to 400 nm and which comprises: (a) at least one metal alkoxide chosen from zirconium, titanium and aluminum alkoxides, (b) at least one organic UV-A sunscreen agent, the maximum absorption wavelength of which is less than 370 nm, (c) at least one functionalized organic polymer or one precursor of such a polymer, or at least one functionalized silicone polymer or one precursor of such a polymer, (d) at least one solvent, and {e) an amount of water sufficient for the partial and/or complete hydrolysis of the metal alkoxide and its condensation.
The term “organic UV-A sunscreen agent” is understood to mean any organic compound which absorbs UV radiation within the 320-400 nm wavelength range.
The metal alkoxides are chosen from the group composed of: {1) metalloorganic compounds corresponding to one of the following formulae:
M(OR), (Ta)
R-M(OR), (Ib) (RO). M-R"-M'(OR |), (Ic)
R-M(OR), 2 (Id)
R’ in which:
- - 4 =
M and M’ represent, independently of one another, a ) zirconium, titanium or aluminum atom, n and n’ denote the respective valencies of the metal atoms represented by M and M’,
R; represents a saturated or unsaturated and linear or branched C,5,, preferably C,,, hydrocarbonaceous group optionally comprising a heteroatom, such as a nitrogen, sulfur, oxygen or phosphorus atom, and more preferably a linear or branched C,;,, preferably C,, alkyl group,
R and R’ represent, independently of one another, a saturated or unsaturated and linear, branched or cyclic
Ci.30» preferably C,.,,, hydrocarbonaceous group optionally comprising a heteroatom, such as a nitrogen, phosphorus, sulfur or oxygen atom, such as, for example, a linear or branched alkyl group, a cycloalkyl group or an aryl group, it being possible for said R and R’ groups to be substituted by groups capable of reacting with the functionalized organic or silicone polymer, such as, for example, halogen atoms, the hydroxyl, acyl, carboxyl, ester, thiol, alkylthioalkyl, epoxy, isocyanate, thiocyanate, ureido, thioureido, urethane, imidazolo, morpholino or pyrrolo groups, groups comprising ethylenic unsaturation, such as the (meth)acrylic and vinyl groups, halogenated groups, such as perfluorinated groups, hydroxylated or carboxylated groups, phosphonic, phosphonate, phosphate, pyrophosphate, phosphonium, sulfonate, amine, quaternary ammonium, amide, amino acid and polypeptide groups, the acetic acid, acetoacetate (ACAC) or ethyl acetoacetate group, or a group deriving from EDTA and its derivatives, and the like, and it being possible for said R and R’ groups to additionally comprise a cosmetically or dermatologically active group chosen, for example, from a colorant group, a photochromic group, a group for screening out UV radiation, a group for promoting adhesion to keratinous substances (such as groups of amide, urethane, ures, » : hydroxyl, carboxyl, amino acid or polypeptide type), a he group for facilitating the removal of makeup, a bactericidal group, a chelating group which can in particular complex polyvalent cations, a hydroxy acid, a neurosuppressant, a group for combating hair loss, an antioxidizing group, a group for combating free radicals or a vitamin-carrying group,
R” represents a saturated or unsaturated and linear, branched or cyclic divalent C,.;,, hydrocarbonaceous group 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, it being possible for said R” group to be substituted by groups capable of reacting with the organic or silicone polymer, such as those defined above, and it being possible for said R” group additionally to comprise a cosmetically or dermatologically active group, such as those defined above; (2) complexed or chelated metalloorganic compounds corresponding to one of the following formulae:
M(OR |), 5 (Xx (IIa)
R-M(OR),,. 1px (Xx (IIb) (X)x (OR 1px M-R"-M'(OR pp (Xx (IIc)
R-M(OR );.2.5x(X)x (I1d)
R' in which:
M, M, n, n’, R,, R, R” and R” have the same meanings as those given for the above formulae (Ia) to (Id),
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 bonded to a group capable of reacting with said functionalized organic polymer or said functionalized silicone polymer (c), such as, for example, those defined above, and which can comprise a cosmetically or dermatologically active . group, such as, for example, those defined above, x represents the number of X ligands; and b represents the number of bonding atoms of the X ligand.
The term “monodentate ligand” is understood to mean a group comprising a single atom which can bond to the central metal atom.
The term “chelating group” is understood to mean a polydentate ligand bonded to a single central metal atom by more than one doublet-donating atom.
Mention may be made, as examples of such monodentate or polydentate ligands (X), of sulfuric acids, sulfonic acids, phosphonic acids, phosphoric acids, carboxylic acids, ketones, p-diketones, esters, B- ketoesters, amines, P-ketcamines, amino acids, preferably a- or P-hydroxylated amino acids, and their derivatives, a- or P-hydroxy acids, ethers and polyethers, imines, optionally hydroxylated amides, azo compounds, thiols, ureas, thioether sulfoxides, thioether sulfones, optionally cyclic thioethers, di (thiocethers), moncalcohols or polyols, dextrin and its derivatives, or thiazolidines.
Mention may in particular be made of diketones, such as 2,4-pentanedione, 2,4-hexafluoropentanedione or 2,2,6,6-tetramethyl-3, 5-heptanedione; salicylic acid and its derivatives, such as 4 ~ or 5- ( (meth)acrylamino) salicylic [sic] acid; lactic, succinic, acetic and citric acid; (meth)acrylic acid esters, such as acetoxyethyl methacrylate or methyl o- hydroxy (meth) acrylate; ethyl acetoacetate, methyl acetoacetate and acetylacetone; EDTA; polyethers of low molecular mass, such as poly(ethylene glycol)s and poly (propylene glycol)s; polyethyleneimines; lysine and its derivatives, such as g-N-(meth)acryloyl-L-lysine; cysteine and its derivatives, such as N-acetylcysteine, carboxymethylcysteine, cystine or N,N’-diacetylcystine;

Claims (1)

  1. PCT/FR00/02687 : CLAIMS
    1. Material capable of being obtained by the sol- gel route comprising: (a) at least one metal alkoxide chosen from zirconium, titanium and aluminum alkoxides, (b) at least one organic UV-A sunscreen agent having a maximum absorption wavelength of less than 370 nm, (c) at least one functionalized organic polymer or one precursor of such a polymer, or at least one functionalized silicone polymer or one precursor of such a polymer, {d) at least one solvent, and (e) an amount of water sufficient for the partial and/or complete hydrolysis of the metal alkoxide and its condensation, said material having a maximum absorption wavelength (Aax) Which is situated in the range from 370 to 400 nm.
    2. Material according to Claim 1, characterized in that the metal alkoxide is chosen from the group composed of: (1) metalloorganic compounds corresponding to one of the following formulae: M(OR), R-M(OR)),_ R00). M-R"-M'(OR}) R-M(OR)), ; in which: M and M’ represent, independently of one another, a zirconium, titanium or aluminum atom, n and n’ denote the respective valencies of the metal atoms represented by M and M’/, R, represents a saturated or unsaturated and linear or AMENDED SHEET
    °! PCT/FR00/02687 branched carbon containing compound selected from the groups consisting of Ci.3, Cis, hydrocarbonaceous group optionally comprising a heteroatom, selected from a group consisting of nitrogen, sulfur, oxygen or phosphorus atom, and an alkyl group, R and R’ represent, independently of one another, a saturated or unsaturated and linear, branched or cyclic carbon containing compound selected from the group consisting of Cis, 7 Ci20, hydrocarbonaceous group optionally comprising a heteroatom, selected from a group consisting of nitrogen, phosphorus, sulfur or oxygen atom, selected from the group consisting of a linear or branched alkyl group, a cycloalkyl group or an aryl group, it being possible for said R and R’ groups to be substituted by groups capable of reacting with the organic or silicone polymer and it being possible for said R and R’ groups to additionally comprise a cosmetically or dermatologically active group, R” represents a carbon containing compound selected from the group consisting of saturated or unsaturated and linear, branched or cyclic divalent Ci-30/s : hydrocarbonaceous group optionally comprising a heteroatom, selected from the group consisting of nitrogen, phosphorus, sulfur or oxygen atom selected from the group consisting of, a linear or branched alkylene group, a cycloalkylene group or an arylene group, it being possible for said R” group to be substituted by groups capable of reacting with the organic or silicone polymer and it being possible for said R” group additionally to comprise a cosmetically or dermatologically active group; (2) complexed or chelated metalloorganic compounds corresponding to one of the following formulae:
    AMENDED SHEET
    * PCT/FR0O0/02687 M(OR |) px (XX), (ITa) R-M(OR).1.5x(X), (IIb) (X) (OR, In-1.5xM-R"-M'(OR| Int (Kg (IIc) R-M(OR ).5.6x (Xx (I1d) R' in which: M, M'", n, n’, R;, R, R’ and R” have the same meanings as those given for the above formulae (Ia) to (Id), 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 bonded to a group capable of reacting with said functionalized organic polymer or said functionalized silicone polymer (c), and which can comprise a cosmetically or dermatologically active group, X represents the number of X ligands; and b represents the number of bonding atoms of the X ligand.
    3. Material according to Claim 2, characterized in that said group capable of reacting with the functionalized organic polymer or the functionalized silicone polymer (c) carried by the R, R’ or R” group and/or by the X ligand can be chosen from halogen atoms, the hydroxyl, acyl, carboxyl, ester, thiol, alkylthioalkyl, epoxy, isocyanate, thiocyanate, ureido, thioureido, urethane, imidazolo, morpholino or pyrrolo groups, groups comprising ethylenic unsaturation, such as the (meth)acrylic and vinyl groups, halogenated groups, such as perfluorinated groups, hydroxylated or carboxylated groups, phosphonic, phosphonate, phosphate, pyrophosphate, phosphonium, sulfonate, amine, quaternary ammonium, amide, amino acid and polypeptide groups, the acetic acid, acetoacetate (ACAC) or ethyl acetoacetate group, or a group deriving AMENDED SHEET
    PCT/FR00/02687 from EDTA and its derivatives.
    4. Material according to Claim 2 or 3, characterized in that the monodentate or polydentate ligand X is chosen from sulfuric acids, sulfonic acids, phosphonic acids, phosphoric acids, carboxylic acids, ketones, f-diketones, esters, P-ketoesters, amines, pB- ketoamines, amino acids, o- or PB-hydroxylated amino acids, and their derivatives, a- or B-hydroxy acids, ethers and polyethers, imines, optionally hydroxylated amides, azo compounds, thiols, ureas, thioether sulfoxides, thioether sulfones, optionally cyclic thioethers, di(thiocethers), monoalcohols or polyols, dextrin and its derivatives, or thiazolidines.
    5. Material according to any one of the preceding claims, characterized in that the metal alkoxide is chosen from tetra-n-propyl zirconate, tetraisopropyl zirconate, titanium tetraisopropoxide and aluminum tri- sec-butoxide.
    6. Material according to any one of the preceding claims, characterized in that the metal alkoxide is present in an amount ranging from 0.1% by weight to 99% by weight, with respect to the total weight of the material.
    7. Material according to any one of the preceding claims, characterized in that the metal alkoxide is present in an amount ranging from 0.5% to 80% by weight, with respect to the total weight of the material.
    8. Material according to any one of the preceding claims, characterized in that the organic UV-A sunscreen agent is chosen from: — dibenzoylmethane derivatives, — camphor derivatives, - benzimidazole derivatives, AMENDED SHEET
    ?° PCT/FR0O0/02687 - benzoxazole derivatives, - benzophenone derivatives, - silane or polyorganosiloxane derivatives comprising benzophenone group (s), - anthranilates, and - their mixtures.
    S. Material according to any one of the preceding claims, characterized in that the organic Uv-A sunscreen agent is chosen from: - 2-methyldibenzoylmethane, - 4-methyldibenzoylmethane, - 4-isopropyldibenzoylmethane, - 4-tert-butyldibenzoylmethane, - 2,4-dimethyldibenzoylmethane, - 2,5-dimethyldibenzoylmethane, - 4,4'-diisopropyldibenzoylmethane, - 4,4'-dimethoxydibenzoylmethane, - 4d-tert-butyl-4'-methoxydibenzoylmethane, - 2-methyl-5-isopropyl-4"'-methoxydibenzoyl- methane, - 2-methyl-5-tert-butyl-4'-methoxydibenzoyl- methane, } - 2,4-dimethyl-4'-methoxydibenzoylmethane, - 2,6-dimethyl-4-tert-butyl-4'-methoxydi- benzoylmethane.
    10. Material according to any one of the preceding claims, characterized in that the organic UvV-A sunscreen agent is 4-tert-butyl-4'-methoxydibenzoyl- methane.
    11. Material according to any one of claims 1 to 10, characterized in that the organic UV-A sunscreen agent is present in an amount ranging from 0.1% by weight to 60% by weight, with respect to the total weight of the material.
    12. Material according to any one of claims 1 to . =~ = : 10, characterized in that the organic UV-A sunscreen AMENDED SHEET
    7 PCT/FR00/02687 agent is present in an amount ranging from 0.1% to 30%
    by weight, with respect to the total weight of the material
    13 Material according to any one of the preceding claims, characterized in that the functionalized organic or silicone polymer is a homopolymer or random, block and/or graft copolymer chosen from:
    (a) alkyloxazoline homopolymers and copolymers;
    (b) homopolymers and copolymers of (meth)acrylic acid, of crotonic acid, of maleic acid, of itaconic acid, of styrenesulfonic acid, of 2— (acrylamido)methylpropanesulfonic acid, of 2— sulfoethyl methacrylate, of vinylsulfonic acid and/or of vinylphosphonic acid;
    (c) homopolymers of acrylic or methacrylic esters or amides and their copolymers with comonomers chosen from unsaturated carboxylic acids, sulfonic acids, phosphonic acids, vinyl esters and ethers, olefins, styrene, substituted styrenes, fluoro- and perfluoroclefins, perfluoroalkyl (meth) acrylates, fluorovinyl compounds and unsaturated organosilanes, organosiloxanes or organopolysiloxanes;
    (d) vinyl alcohol homopolymers and copolymers;
    (e) homopolymers of vinyl and/or allyl and/or methallyl esters or amides and their copolymers with comonomers chosen from unsaturated carboxylic acids, sulfonic acids, phosphonic acids, vinyl esters and ethers, olefins, styrene, substituted styrenes, fluoro- and perfluorcolefins, perfluoroalkyl (meth) acrylates, fluorovinyl compounds, and unsaturated organosilanes, organosiloxanes or organopolysiloxanes;
    (f) polyethers;
    (g) polyesters; CT Co
    (h) homopolymers and copolymers of olefins or of
    AMENDED SHEET
    PCT/FR0O0/02687 cycloolefins; (1) polyamides and polyesteramides; (J) polyurethanes and polyureas which can comprise polyether, polyester and/or polyorganosiloxane blocks; (k) fluoropolymers; (1) natural polymers and modified natural polymers; (m) polyorganosiloxanes; (n) polyorganophosphazenes; (0) polysilanes, ©polycarbosilanes or polysilazanes; and (p) mixtures of these polymers.
    14. Material according to any one of the preceding claims, characterized in that the functionalized organic or silicone polymer is chosen from poly (2- ethyl-2-oxazoline), a terpolymer of vinyl acetate, of vinyl 4-tert-butylbenzoate and of crotonic acid (62/25/10), polydimethylsiloxane-diols, poly(ethylene glycol)s, poly(amylalcohol) and poly (vinylpyrrolidone).
    15. Material according to Claim 14, characterized in that the functionalized organic or silicone polymer is a polydimethylsiloxane-diol.
    16. Material according to any one of claims 1 to 15, characterized in that the functionalized organic or silicone polymer is present in an amount ranging from
    0.1% by weight to 99% by weight, with respect to the total weight of the material.
    17. Material according to any one of claims 1 to 15, characterized in that the functionalized organic or silicone polymer is present in an amount ranging from
    0.5% to 80% by weight, with respect to the total weight ’ of the material.
    18. Material according to any one of the preceding claims, characterized in that the solvent is an alcohol.
    19. Material according to Claim 18, characterized AMENDED SHEET
    > PCT/FR0O0/02687 in that the alcohol is a linear or branched lower alcohol.
    20. Material according to Claim 19, characterized in that the alcohol is ethanol.
    21. Process for shifting the maximum absorption wavelength (Ax) of an organic UV-A sunscreen agent having a Am.x of less than 370 nm into the range from 370 to 400 nm, characterized in that it comprises the combination of this screening agent with a sol comprising at least one functionalized organic polymer or one precursor of such a polymer, or at least one functionalized silicone polymer or one precursor of such a polymer, at least one metal alkoxide chosen from zirconium, titanium and aluminum alkoxides, at least one solvent and an amount of water sufficient for the partial and/or complete hydrolysis of the metal alkoxide and its condensation.
    22. Process according to Claim 21, characterized in that the metal alkoxide is chosen from the group composed of: (1) metalloorganic compounds corresponding to one of the following formulae: M(OR,), (Ia) R-M(OR)), (Ib) (R;0), M-R"-M'(OR),. (Ic) R-M(OR),, 5 (Id) R' in which: M and M’ represent, independently of one another, a zirconium, titanium or aluminum atom, n and n’ denote the respective valencies of the metal atoms represented by M and M’, R; represents a saturated or unsaturated and linear or branched carbon containing compound selected for the group consisting of Ci.z, ; Cig, hydrocarbonaceous group AMENDED SHEET
    > PCT/FR00/02687 optionally comprising a heteroatom, selected from a group consisting of nitrogen, sulfur, oxygen Or phosphorus atom, and a linear or branched C;.3, alkyl group, R and R’ represent, independently of one another, a saturated or unsaturated and linear, branched or cyclic carbon containing compound selected from the group consisting of Ciso0 ; Cp20, hydrocarbonaceous group optionally comprising a heteroatom, selected from the group consisting of nitrogen, phosphorus, sulfur or oxygen atom, selected from the group consisting of a linear or branched alkyl group, a cycloalkyl group or an aryl group, it being possible for said R and R’ groups to be substituted by groups capable of reacting with the organic or silicone polymer and it being possible for said R and R’ groups to additionally comprise a cosmetically or dermatologically active group, R” represents a saturated or unsaturated and linear, branched or cyclic divalent Cj;-30, hydrocarbonaceous group optionally comprising a heteroatom, selected from the group consisting of nitrogen, phosphorus, sulfur or oxygen atom, , selected from the group consisting of a linear or branched alkylene group, a cycloalkylene group or an arylene group, it being possible for said R” group to be substituted by groups capable of reacting with the organic or silicone polymer and it being possible for said R” group additionally to comprise a cosmetically or dermatologically active group; (2) complexed or chelated metalloorganic compounds corresponding to one of the following formulae:
    MOR) p(X) (11a)
    R-M(OR )p,.1.px (Xx (IIb)
    (Xx (OR) 1px M-R"-M'(OR) 1 px (XK), (IIc)
    R-M(OR 1) .2.5x(X)y AMESDED SHEET
    R'
    PCT/FR0O0/02687 in which: M, M', n, n’, Ri, R, R! and R” have the same meanings as those given for the above formulae (Ia) to (Id), 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 bonded to a group capable of reacting with said functionalized organic polymer or said functionalized silicone polymer (c), and which can comprise a cosmetically or dermatologically active group, X represents the number of X ligands; and b represents the number of bonding atoms of the X ligand.
    23. Process according to Claim 22, characterized in that said group capable of reacting with the functionalized organic polymer or the functionalized silicone polymer (c) carried by the R, R’ or R” group and/or by the X ligand can be chosen from halogen atoms, the hydroxyl, acyl, carboxyl, ester, thiol, alkylthioalkyl, epoxy, isocyanate, thiocyanate, ureido, thioureido, urethane, imidazolo, morpholino or pyrrolo groups, groups comprising ethylenic unsaturation, such as the (meth)acrylic and vinyl groups, halogenated groups, such as perfluorinated groups, hydroxylated or carboxylated groups, phosphonic, phosphonate, phosphate, pyrophosphate, phosphonium, sulfonate, amine, quaternary ammonium, amide, amino acid and polypeptide groups, the acetic acid, acetoacetate (ACAC) or ethyl acetoacetate group, or a group deriving from EDTA and its derivatives.
    24. Process according to Claim 22 or 23, characterized in that the monodentate or polydentate ligand X is chosen from sulfuric acids, sulfonic acids, phosphonic acids, phosphoric acids, carboxylic acids, ketones, PB-diketones, esters, f-ketoesters, amines, B- AMENDED SHEET
    °° PCT/FR0O0/02687 ketoamines, amino acids, o- or B-hydroxylated amino acids, and their derivatives, a- or B-hydroxy acids, ethers and polyethers, imines, hydroxylated amides, azo compounds, thiols, ureas, thioether sulfoxides, thioether sulfones, cyclic thioethers, di(thiocethers), monoalcohols or polyols, dextrin and its derivatives, or thiazolidines.
    25. Process according to any one of Claims 21 to 24, characterized in that the metal alkoxide is chosen from tetra-n-propyl zirconate, tetraisopropyl zirconate, titanium tetraisopropoxide and aluminum tri- sec-butoxide.
    26. Process according to any one of Claims 21 to 25, characterized in that the organic UV-A sunscreen agent is chosen from: - dibenzoylmethane derivatives, - camphor derivatives, - benzimidazole derivatives, - benzoxazole derivatives, - benzophenone derivatives, - silane or polyorganosiloxane derivatives comprising benzophenone group(s), - anthranilates, and - their mixtures.
    27. Process according to any one of Claims 21 to 26, characterized in that the organic UV-A sunscreen agent is chosen from: - 2-methyldibenzoylmethane, - 4-methyldibenzoylmethane, - 4-isopropyldibenzoylmethane, - 4-tert-butyldibenzoylmethane, - 2,4-dimethyldibenzoylmethane, - 2,5-dimethyldibenzoylmethane, - 4,4'-diisopropyldibenzoylmethane, - 4,4'-dimethoxydibenzoylmethane, AMENDED SHEET
    > PCT/FR00/02687 ~ 4-tert-butyl-4'-methoxydibenzoylmethane, —- 2-methyl-5-isopropyl-4'-methoxydibenzoyl- methane, —- Z-methyl-5-tert-butyl-4'-methoxydibenzoyl- methane, - 2,4-dimethyl-4'-methoxydibenzoylmethane, - 2,6-dimethyl-4-tert-butyl-4'-methoxydi- benzoylmethane.
    28. Process according to any one of Claims 21 to 27, characterized in that the organic UV-A sunscreen agent is 4-tert-butyl-4'-methoxydibenzoylmethane. : 29. Process according to any one of Claims 21 to 28, characterized in that the functionalized organic or silicone polymer is a homopolymer or random, block and/or graft copolymer chosen from: (a) alkyloxazoline homopolymers and copolymers; (b) homopolymers and copolymers of (meth)acrylic acid, of crotonic acid, of maleic acid, of itaconic acid, of styrenesul fonic acid, of 2- (acrylamido)methylpropanesulfonic acid, of 2- sulfoethyl methacrylate, of vinylsulfonic acid and/or of vinylphosphonic acid; oo (c) homopolymers of acrylic or methacrylic esters or amides and their copolymers with comonomers chosen from unsaturated carboxylic acids, sulfonic acids, phosphonic acids, vinyl esters and ethers, olefins, styrene, substituted styrenes, fluoro- and perfluoroolefins, perfluoroalkyl (meth) acrylates, fluorovinyl compounds and unsaturated organosilanes, organosiloxanes or organopolysiloxanes; (d) vinyl alcohol homopolymers and copolymers; (e} homopolymers of vinyl and/or allyl and/or methallyl esters or amides and their copolymers with comonomers chosen from unsaturated carboxylic acids, sulfonic acids, phosphonic acids, wvinyl AMENDED SHEET
    > PCT/FR0O0/02687 esters and ethers, olefins, styrene, substituted styrenes, fluoro- and perfluoroolefins, perfluorocalkyl (meth)acrylates, fluorovinyl compounds, and unsaturated organosilanes, organosiloxanes or organopolysiloxanes; (f) polyethers; (g) polyesters; (h) homopolymers and copolymers of olefins or of cycloolefins; (1) polyamides and polyesteramides; (J) polyurethanes and polyureas which can comprise polyether, polyester and/or polyorganosiloxane blocks; {k) fluoropolymers; (1) natural polymers and modified natural polymers; (m) polyorganosiloxanes; (n) polyorganophosphazenes; (0) polysilanes, polycarbosilanes or polysilazanes; and (p) mixtures of these polymers.
    30. Process according to any one of Claims 21 to 29, characterized in that the functionalized organic or silicone polymer is chosen from poly (2-ethyl-2- oxazoline), a terpolymer of vinyl acetate, of vinyl 4- tert-butylbenzoate and of crotonic acid (62/25/10), polydimethylsiloxane-diols, poly(ethylene glycol) s, poly (amylalcohol) and poly(vinylpyrrolidone).
    31. Process according to Claim 30, characterized in that the functionalized organic or silicone polymer is a polydimethylsiloxane-diol.
    32. Process according to any one of Claims 21 to 31, characterized in that the solvent is a linear or branched lower alcohol.
    33. Process according to Claim 32, characterized in that the alcohol is ethanol. - -
    34. Process according to any one of Claims 21 to AMENDED SHEET
    > PCT/FRO0/02687 33, characterized in that the metal alkoxide is mixed with a solution of functionalized organic or silicone polymer before the addition of the screening agent.
    35. Cosmetic and/or dermatological composition, characterized in that it comprises, in a cosmetically and/or dermatologically acceptable vehicle, an effective amount of the material according to any one of Claims 1 to 20.
    36. Cosmetic and/or dermatological compesition according to Claim 35, characterized in that the material is in the form of particles obtained by drying and milling.
    37. Cosmetic and/or dermatological composition according to Claim 35 or 36, characterized in that the effective amount of the material according to any one of Claims 1 to 20 lies within the range from 1% by weight to 99% by weight with respect to the total weight of the cosmetic and/or dermatological composition.
    38. Cosmetic and/or dermatological composition according to any one of Claims 35 to 37, characterized in that the effective amount of the material according to any one of Claims 1 to 20 lies within the range from to 60% by weight with respect to the total weight of the cosmetic and/or dermatological composition.
    39. Cosmetic and/or dermatological composition according to any one of Claims 35 to 38, characterized in that the mean size of the particles obtained by drying and milling the material according to any one of Claims 1 to 20 lies within the range from 0.1 pum to um.
    40. Cosmetic and/or dermatological composition according to Claim 39, characterized in that the mean size of the particles obtained by drying and milling the material according to any one of the Claims 1 to 20 AMENDED SHEET
    +0 PCT/FRO0/02687 lies within the range from 0.1 pm to 10 um.
    41. Cosmetic and/or dermatological composition according to any one of Claims 35 to 40, characterized in that an additive chosen from sunscreen agents other than organic UV-A sunscreen agents, agents for the artificial tanning and/or browning of the skin, pigments, fatty substances, organic solvents, thickeners, softeners or antioxidants can additionally be added. 42, Material capable of being obtained by the sol- gel route, including any new and inventive integer or combination thereof herein described. 43, Process for shifting the maximum absorption wavelength (Awx) of an organic UV-A sunscreen agent having a Amx of less than 370 nm into the range from 370 to 400 nm, including any new and inventive integer or combination thereof herein described. 44, Cosmetic and/or dermatological composition, including any new and inventive integer or combination thereof herein described. AMENDED SHEET
ZA200104121A 1999-10-01 2001-05-21 Material comprising an organic US-A filter and method for displacing the maximum absorption wavelength. ZA200104121B (en)

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FR2799119B1 (en) * 1999-10-01 2001-11-30 Oreal PROCESS FOR IMPROVING THE STABILITY TO UV RADIATION OF PHOTOSENSITIVE SOLAR FILTERS
EP1411888A2 (en) 2001-07-31 2004-04-28 MERCK PATENT GmbH Sunscreen composition
FR2842418A1 (en) * 2002-07-19 2004-01-23 Oreal PHOTOSTABILIZED MATERIAL CONTAINING SOLAR-GEL-PRODUCED DIBENZOYLMETHANE SOLAR FILTER AND COSMETIC AND / OR DERMOTOLOGICAL COMPOSITION CONTAINING SUCH MATERIAL
FR2842419A1 (en) * 2002-07-19 2004-01-23 Oreal A method of broadening the UV absorption spectrum of an organic UVA filter used in cosmetic composition to protect against solar radiation by immobilizing it in a matrix produced by sol-gel from a silicon alkoxide and a surfactant
CN102552068B (en) * 2011-12-26 2016-01-20 上海应用技术学院 Polysiloxane composite particles of the chemical sun that a kind of esters of coated salicylic acid or derivatives thereof is formed and preparation method thereof
CN102552064B (en) * 2011-12-26 2015-03-18 上海应用技术学院 Polysiloxane composite particle coated with sunscreen chemical formed by esters of p-aminobenzoic acid or derivatives thereof and preparation method of same
US9222006B2 (en) * 2013-02-28 2015-12-29 The Boeing Company Joining a thermoplastic material and a metal
EP3426706A1 (en) 2016-03-08 2019-01-16 Living Proof, Inc. Long lasting cosmetic compositions
EP3681921A2 (en) 2017-09-13 2020-07-22 Living Proof, Inc. Color protectant compositions
JP7244495B2 (en) 2017-09-13 2023-03-22 リビング プルーフ インコーポレイテッド Long lasting cosmetic composition
RU2742752C1 (en) * 2019-08-22 2021-02-10 федеральное государственное автономное образовательное учреждение высшего образования "Национальный исследовательский университет ИТМО" (Университет ИТМО) Medicinal preparation in form of sol for treating a disease and/or condition characterized by violation of skin integrity, and a method for preparing it

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FR2799119B1 (en) * 1999-10-01 2001-11-30 Oreal PROCESS FOR IMPROVING THE STABILITY TO UV RADIATION OF PHOTOSENSITIVE SOLAR FILTERS

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AU759357B2 (en) 2003-04-10
FR2799120A1 (en) 2001-04-06
WO2001024768A3 (en) 2002-07-11
CZ20011809A3 (en) 2001-10-17
JP2003510342A (en) 2003-03-18
KR20010080582A (en) 2001-08-22
PL347767A1 (en) 2002-04-22
WO2001024768A2 (en) 2001-04-12
RU2212881C2 (en) 2003-09-27
CN1352544A (en) 2002-06-05
HUP0300234A2 (en) 2003-08-28
BR0007188A (en) 2001-09-04
AU7668300A (en) 2001-05-10

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