초록 ▼

The photostabilizing electronic excited state energy—particularly singlet state energy from a UV-absorbing molecule has been found to be readily transferred to (accepted by) α-cyanodiphenylacrylate compounds of formulas (I) and (V) having an alkoxy radical preferably in the four (para)

The photostabilizing electronic excited state energy—particularly singlet state energy from a UV-absorbing molecule has been found to be readily transferred to (accepted by) α-cyanodiphenylacrylate compounds of formulas (I) and (V) having an alkoxy radical preferably in the four (para) position (hereinafter methoxy crylenes) on one or both of the phenyl rings: wherein at least one of R1 and R2 is a straight or branched chain C1-C12 alkoxy radical, preferably C1-C8, more preferably C1-C4, and most preferably methoxy, and any non-alkoxy radical R1 or R2 is hydrogen; and R3 is a straight or branched chain C1-C24 alkyl radical, preferably C12-C24, more preferably C20; wherein A and B are the same or different and are selected from the group consisting of oxygen, amino and sulfur; R1 and R3 are the same or different and are selected from the group consisting of C1-C30 alkyl, C2-C30 alkylene, C2-C30 alkyne, C3-C8 cycloalkyl, C1-C30 substituted alkylene, C2-C30 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl and substituted heterocycloalkyl; R2 is selected from the group consisting of C1-C30 alkyl, C2-C30 alkylene, C2-C30 alkyne, C3-C8 cycloalkyl, C1-C30 substituted alkyl, C3-C8 substituted cycloalkyl, C1-C30 substituted alkylene, C2-C30 substituted alkyne; R4, R5, R6 and R7 are the same or different and are selected from the group consisting of C1-C30 alkoxy straight chin on branched and a, b, c and d are each either 0 or 1, and a, b, c and d add up to 1, 2, 3, or 4.

대표청구항 ▼

The invention claimed is: 1. A photostabilized photoactive sunscreen composition comprising a mixture of a photon-excited photoactive compound that reaches a singlet excited state when exposed to UV radiation and a compound of formula (I) in an amount sufficient to accept the singlet excited state

The invention claimed is: 1. A photostabilized photoactive sunscreen composition comprising a mixture of a photon-excited photoactive compound that reaches a singlet excited state when exposed to UV radiation and a compound of formula (I) in an amount sufficient to accept the singlet excited state energy from said photoactive compound to quench the singlet excited state energy from the photon-excited photoactive compound and transfer the singlet excited state energy from the photon-excited photoactive compound to the compound of formula (I) thereby returning the photon-excited photoactive compound to its ground state so that the photon-excited photoactive compound can absorb more photons from UV radiation before it undergoes a photochemical reaction destructive to its UV-absorbing capability, thereby photostabilizing said photoactive compound: wherein one of R1 and R2 is a straight or branched chain C1-C30 alkoxy radical, and the other R1 or R2 is hydrogen; and R3 is a straight or branched chain C1-C30 alkyl radical. 2. The photostabilized photoactive composition of claim 1, wherein R1 is methoxy and R2 is hydrogen. 3. The photostabilized photoactive composition of claim 2, wherein R3 is a C12-C30 straight chain or branched alkyl. 4. The photostabilized photoactive composition of claim 1, wherein R2 is methoxy and R1 is hydrogen. 5. The photostabilized photoactive composition of claim 1, wherein the compound of formula (I) is present in an amount in the weight range of 0.1% to 20%, based on the total weight of the composition. 6. The photostabilized photoactive composition of claim 1, wherein the compound of formula (I) is present in an amount in this weight range of 0.5% to 10%, based on the total weight of the composition. 7. The photostabilized photoactive composition of claim 1, wherein the compound of formula (I) is present in an amount in this weight range of 0.1% to 10%, based on the total weight of the composition. 8. The photostabilized photoactive composition of claim 7, wherein the compound of formula (I) is present in an amount in this weight range of 3% to 8%, based on the total weight of the composition. 9. The photostabilized photoactive composition of claim 1, wherein the photoactive compound is selected from the group consisting of p-aminobenzoic acid and salts and derivatives thereof; anthranilate and derivatives thereof; dibenzoylmethane and derivatives thereof; salicylate and derivatives thereof; cinnamic acid and derivatives thereof; dihydroxycinnamic acid and derivatives thereof; camphor and salts and derivatives thereof; trihydroxycinnamic acid and derivatives thereof; dibenzalacetone naptholsulfonate and salts and derivatives thereof; benzalacetophenone naphtholsulfonate and salts and derivatives thereof; dihydroxy-naphthoic acid and salts thereof; o-hydroxydiphenyldisulfonate and salts and derivatives thereof; p-hydroxdydiphenyldisulfonate and salts and derivatives thereof; coumarin and derivatives thereof; diazole derivatives; quinine derivatives and salts thereof; quinoline derivatives; hydroxyl-substituted benzophenone derivatives; naphthalate derivatives; methoxy-substituted benzophenone derivatives; uric acid derivatives; vilouric acid derivatives; tannic acid and derivatives thereof; hydroquinone; benzophenone derivatives; 1,3,5-triazine derivatives; phenyldibenzimidazole tetrasulfonate and salts and derivatives thereof; terephthalyidene dicamphor sulfonic acid and salts and derivatives thereof; methylene bis-benzotriazolyl tetramethylbutylphenol and salts and derivatives thereof; bis-ethylhexyloxyphenol methoxyphenyl triazine and salts, diethylamino hydroxyl benzoyl and derivatives thereof; and combinations of the foregoing. 10. The photostabilized photoactive composition of claim 9, wherein the photoactive compound comprises a derivative of cinnamic acid. 11. The photostabilized photoactive composition of claim 10, wherein the photoactive compound comprises 2-ethylhexyl-p-methoxycinnamate. 12. The photostabilized photoactive composition of claim 10, wherein the photoactive compound comprises isoamyl methoxycinnamate. 13. The photostabilized photoactive composition of claim 1, wherein the photoactive compound comprises a dibenzoylmethane derivative. 14. The photostabilized photoactive composition of claim 13, further including a cinnamate ester. 15. The photostabilized photoactive composition of claim 14, wherein the cinnamate ester is selected from the group consisting of 2-ethylhexyl p-methoxycinnamate, isoamyl p-methoxycinnamate, and a combination thereof. 16. The photostabilized photoactive composition of claim 15 wherein the cinnamate ester is 2-ethylhexyl p-methoxycinnamate. 17. The photostabilized photoactive composition of claim 16, further including bis-ethylhexyloxyphenol methoxyphenyl triazine in an amount of 0.1 to 10 wt. %. 18. The photostabilized photoactive composition of claim 16, further including diethylhexyl syringylidene malonate in an amount of 0.1 to 10 wt. %. 19. The photostabilized photoactive composition of claim 16, further including methylene bis-benzotriazoyl tetramethylbutyl phenol in an amount of 0.1 to 10 wt. %. 20. The photostabilized photoactive composition of claim 16, further including diethylamino hydroxybenzoyl hexylbenzoate in an amount of 0.1 to 10 wt. %. 21. The photostabilized photoactive composition of claim 16, further including disodium phenyldibenzylimidazole sulfonic acid in an amount of 0.1 to 10 wt. %. 22. The photostabilized photoactive composition of claim 16, further including 4-methylbenzilidene camphor. 23. The photostabilized photoactive composition of claim 16, further including phenylbenzimidazole sulfonic acid or salt thereof in an amount of 0.1 to 10 wt. %. 24. The photostabilized photoactive composition of claim 13, wherein the dibenzoylmethane derivative comprises butylmethoxy dibenzoylmethane. 25. The photostabilized photoactive composition of claim 24, further including a salicylate or a derivative thereof in an amount of 0.1 to 10 wt %. 26. The photostabilized photoactive composition of claim 13, wherein the photoactive compound comprises a dibenzoylmethane derivative selected from the group consisting of 2-methyldibenzoylmethane; 4-methyldibenzoylmethane; 4-isopropyldibenzoylmethane; 4-tert-butyldibenzoylmethane; 2,4-dimethydibenzoylmethane; 2-5-dimethydibenzoylmethane; 4,4-diispropyldibenzoylmethane; 4,4-dimethoxydibenzoylmethane; 4-tert-butyl-4-methoxdibenzoylmethane; 2-methyl-5-isopropy-4-methoxydibenzoylmethane; 2-methyl-5-tert-butyl-4-methoxydibenzoylmethane; 2,4-dimethyl-4-methoxydibenzoymethane; 2,6-dimethyl-4-tert-butyl-4-methoxydibenxoylmethane, and combinations thereof. 27. The photostabilized photoactive composition of claim 26 further including 0.1 to 10 wt. % of a triplet quencher selected from the group consisting of octocrylene, methyl benzylidene camphor, diethylhexyl 2,6-naphthalate, diethylhexyl syringylidene malonate, and combinations thereof. 28. The photostabilized photoactive composition of claim 1, further including a naphthalene dicarboxylic acid ester in an amount of 0.1 to 10 wt %. 29. The photostabilized photoactive composition of claim 28, wherein the naphthalene dicarboxylic acid ester comprises a diethylhexyl 2,6-naphthalene dicarboxylic acid ester. 30. The photostabilized photoactive composition of claim 28 further comprising 0.1 to 10 wt. % benzophenone-3. 31. The photostabilized photoactive composition of claim 28 further comprising 0.1 to 10 wt. % octyl salicylate. 32. The photostabilized photoactive composition of claim 1, further including a salicylate or a derivative thereof in an amount of 0.1 to 10 wt %. 33. The photostabilized photoactive composition of claim 1, further including a benzophenone or a derivative thereof in an amount of 0.1 to 10 wt. %. 34. The photostabilized photoactive composition of claim 33, wherein the benzophenone comprises benzophenone-3 in an amount of 0.1 to 10 wt. %. 35. The photostabilized photoactive composition of claim 33, wherein the photoactive compound is selected from the group consisting of a dibenzoylmethane derivative; Octocrylene; a naphthalene dicarboxylic acid ester; diethylhexyl syringylidene malonate; 4-methylbenzilidene-camphor 4-methylbenzilidene camphor; and combinations thereof. 36. The photostabilized photoactive composition of claim 1, wherein the photoactive compound comprises a 1,3,5-triazine derivative. 37. The photostabilized photoactive composition of claim 1, that includes an ester of cyanodiphenyl propenoic acid. 38. The photostabilized photoactive composition of claim 1, wherein the mixture includes methyl benzylidene camphor. 39. The photostabilized photoactive composition of claim 1, wherein the composition includes a compound selected from the group consisting of methylene bis-benzotriazolyl tetramethylbutylphenol, salts and derivatives thereof; bis-ethylhexyloxyphenol methoxyphenyl triazine, and salts and derivatives thereof. 40. The photostabilized photoactive composition of claim 1, wherein the composition includes a hydroxyl-substituted benzophenone derivative or a methoxy-substituted benzophenone derivative, or a combination thereof. 41. The photostabilized photoactive composition of claim 1, further comprising a diester or polyester of naphthalene dicarboxylic acid selected from the group consisting of compounds of formula (II) and (III), and combinations thereof: wherein R1 and R2 are the same or different and selected from the group consisting of C1-C22 alkyl groups, diols having the structure HO—R4—OH, and polyglycols having the structure HO—R3—(—O—R4—)n—OH; wherein each R3 and R4 is the same or different and selected from the group consisting of C1-C6 straight or branched chain alkyl groups; and wherein m and n are each in a range of 1 to 100. 42. The photostabilized photoactive composition of claim 1, comprising a diester of formula (III) wherein R1 and R2 are 2-ethylhexyl. 43. The photostabilized photoactive composition of claim 1, wherein said mixture includes a cosmetically acceptable carrier. 44. The photostabilized photoactive composition of claim 1, wherein said mixture includes an oil phase having a dielectric constant of at least about 8.