Method of quenching electronic excitation of chromophore-containing organic molecules in photoactive compositions
View Patent ↗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 R 1 and R 2 is a straight or branched chain C 1 -C 12 alkoxy radical, preferably C 1 -C 8 , more preferably C 1 -C 4 , and most preferably methoxy, and any non-alkoxy radical R 1 or R 2 is hydrogen; and R 3 is a straight or branched chain C 1 -C 24 alkyl radical, preferably C 12 -C 24 , more preferably C 20 ; wherein A and B are the same or different and are selected from the group consisting of oxygen, amino and sulfur; R 1 and R 3 are the same or different and are selected from the group consisting of C 1 -C 30 alkyl, C 2 -C 30 alkylene, C 2 -C 30 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 30 substituted alkylene, C 2 -C 30 substituted alkyne, aryl, substituted aryl, heteroaryl, heterocycloalkyl, substituted heteroaryl and substituted heterocycloalkyl; R 2 is selected from the group consisting of C 1 -C 30 alkyl, C 2 -C 30 alkylene, C 2 -C 30 alkyne, C 3 -C 8 cycloalkyl, C 1 -C 30 substituted alkyl, C 3 -C 8 substituted cycloalkyl, C 1 -C 30 substituted alkylene, C 2 -C 30 substituted alkyne; R 4 , R 5 , R 6 and R 7 are the same or different and are selected from the group consisting of C 1 -C 30 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.
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 R 1 and R 2 is a straight or branched chain C 1 -C 30 alkoxy radical, and the other R 1 or R 2 is hydrogen; and R 3 is a straight or branched chain C 1 -C 30 alkyl radical.
2. The photostabilized photoactive composition of claim 1 , wherein R 1 is methoxy and R 2 is hydrogen.
3. The photostabilized photoactive composition of claim 2 , wherein R 3 is a C 12 -C 30 straight chain or branched alkyl.
4. The photostabilized photoactive composition of claim 1 , wherein R 2 is methoxy and R 1 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 R 1 and R 2 are the same or different and selected from the group consisting of C 1 -C 22 alkyl groups, diols having the structure HO—R 4 —OH, and polyglycols having the structure HO—R 3 —(—O—R 4 —) n —OH; wherein each R 3 and R 4 is the same or different and selected from the group consisting of C 1 -C 6 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 R 1 and R 2 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.