Compositions comprising photo-labile perfume delivery systems
Abstract
The present invention relates to photo-labile pro-fragrances, as well as a fragrance raw material delivery system comprising: i) from about 0.001% to about 100% by weight, of a photo-labile pro-fragrance compound having the formula: wherein OR is a unit derived from a fragrance raw material alcohol, HOR; R 1 is one or more electron donating groups; each R 2 is independently hydrogen, C 1 -C 12 alkyl, and mixtures thereof; X is selected from the group consisting of —OH, —NH 2 , —NHR 3 , and mixtures thereof; R 3 is hydrogen, C 1 -C 12 linear or branched alkyl, C 6 -C 10 aryl, and mixtures thereof; and ii) optionally from about 0.001% to about 50% by weight, of one or more fragrance raw materials.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A photo-labile pro-fragrance having the formula:
wherein —OR is a unit derived from a fragrance raw material alcohol, HOR; R 1 is one or more electron donating groups; each R 2 is independently hydrogen, C 1 -C 12 alkyl, C 7 -C 12 alkylenearyl; and mixtures thereof; X is selected from the group consisting of —OH, —NH 2 , —NHR 3 , and mixtures thereof; R 3 is hydrogen, C 1 -C 12 linear or branched alkyl, C 6 -C 10 aryl, C 7 -C 12 alkylenearyl, and mixtures thereof.
2 . A compound according to claim 1 wherein R 1 is —N(R 3 ) 2 , —NHR 3 , —NH 2 , —OH, and —OR 3 wherein R 3 is C 1 -C 12 linear or branched alkyl, phenyl, benzyl, and mixtures thereof.
3 . A compound according to claim 1 wherein R 1 is —NHC(O)R 3 , —NR 3 C(O)R 3 , —OC(O)R 3 , —R 3 , —CH═C(R 3 ) 2 , wherein R 3 is hydrogen, C 1 -C 12 linear or branched alkyl, C 6 -C 10 aryl, and C 7 -C 12 alkylenearyl.
4 . A compound according to claim 1 wherein X is —OH.
5 . A compound according to claim 1 wherein X is —NH 2 .
6 . A compound according to claim 1 wherein X is —NHR 3 .
7 . A compound according to claim 1 having the formula:
wherein OR derives from a fragrance raw material alcohol selected from the group consisting of 4-(1-methylethyl)cyclohexanemethanol, 2,4-dimethyl-3-cyclohexen-1-ylmethanol, 2,4-dimethylcyclohex-1-ylmethanol, 2,4,6-trimethyl-3-cyclohexen-1-ylmethanol, 2-phenylethanol, 1-(4-isopropylcyclohexyl)ethanol, 2-(o-methylphenyl)ethanol, 2-(m-methylphenyl)ethanol, 2-(p-methylphenyl)-ethanol, 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol, 3-phenyl-2-propen-1-ol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, 3-methyl-5-phenylpentan-1-ol, 3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, 2-methyl-4-phenylpentan-1-ol, cis-3-hexen-1-ol, 3,7-dimethyl-6-octen-1-ol, 3,7-dimethyl-2,6-octadien-1-ol, 7-methoxy-3,7-dimethyloctan-2-ol, 6,8-dimethylnonan-2-ol, cis-6-nonen-1-ol, 2,6-nonadien-1-ol, 4-methyl-3-decen-5-ol, benzyl alcohol, 2-methoxy-4-(1-propenyl)phenol, 2-methoxy-4-(2-propenyl)phenol, 4-hydroxy-3-methoxybenzaldehyde, and mixtures thereof.
8 . A compound according to claim 1 having the formula:
wherein OR derives from a fragrance raw material alcohol selected from the group consisting of 4-(1-methylethyl)cyclohexanemethanol, 2,4-dimethyl-3-cyclohexen-1-ylmethanol, 2,4-dimethylcyclohex-1-ylmethanol, 2,4,6-trimethyl-3-cyclohexen-1-ylmethanol, 2-phenylethanol, 1-(4-isopropylcyclohexyl)ethanol, 2-(o-methylphenyl)ethanol, 2-(m-methylphenyl)ethanol, 2-(p-methylphenyl)-ethanol, 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol, 3-phenyl-2-propen-1-ol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, 3-methyl-5-phenylpentan-1-ol, 3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, 2-methyl-4-phenylpentan-1-ol, cis-3-hexen-1-ol, 3,7-dimethyl-6-octen-1-ol, 3,7-dimethyl-2,6-octadien-1-ol, 7-methoxy-3,7-dimethyloctan-2-ol, 6,8-dimethylnonan-2-ol, cis-6-nonen-1-ol, 2,6-nonadien-1-ol, 4-methyl-3-decen-5-ol, benzyl alcohol, 2-methoxy-4-(1-propenyl)phenol, 2-methoxy-4-(2-propenyl)phenol, 4-hydroxy-3-methoxybenzaldehyde, and mixtures thereof.
9 . A compound according to claim 1 having the formula:
wherein OR derives from a fragrance raw material alcohol selected from the group consisting of 4-(1-methylethyl)cyclohexanemethanol, 2,4-dimethyl-3-cyclohexen-1-ylmethanol, 2,4-dimethylcyclohex-1-ylmethanol, 2,4,6-trimethyl-3-cyclohexen-1-ylmethanol, 2-phenylethanol, 1-(4-isopropylcyclohexyl)ethanol, 2-(o-methylphenyl)ethanol, 2-(m-methylphenyl)ethanol, 2-(p-methylphenyl)-ethanol, 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol, 3-phenyl-2-propen-1-ol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, 3-methyl-5-phenylpentan-1-ol, 3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, 2-methyl-4-phenylpentan-1-ol, cis-3-hexen-1-ol, 3,7-dimethyl-6-octen-1-ol, 3,7-dimethyl-2,6-octadien-1-ol, 7-methoxy-3,7-dimethyloctan-2-ol, 6,8-dimethylnonan-2-ol, cis-6-nonen-1-ol, 2,6-nonadien-1-ol, 4-methyl-3-decen-5-ol, benzyl alcohol, 2-methoxy-4-(1-propenyl)phenol, 2-methoxy-4-(2-propenyl)phenol, 4-hydroxy-3-methoxybenzaldehyde, and mixtures thereof.
10 . A compound according to claim 1 having the formula:
wherein OR derives from a fragrance raw material alcohol selected from the group consisting of 4-(1-methylethyl)cyclohexanemethanol, 2,4-dimethyl-3-cyclohexen-1-ylmethanol, 2,4-dimethylcyclohex-1-ylmethanol, 2,4,6-trimethyl-3-cyclohexen-1-ylmethanol, 2-phenylethanol, 1-(4-isopropylcyclohexyl)ethanol, 2-(o-methylphenyl)ethanol, 2-(m-methylphenyl)ethanol, 2-(p-methylphenyl)-ethanol, 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol, 3-phenyl-2-propen-1-ol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, 3-methyl-5-phenylpentan-1-ol, 3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, 2-methyl-4-phenylpentan-1-ol, cis-3-hexen-1-ol, 3,7-dimethyl-6-octen-1-ol, 3,7-dimethyl-2,6-octadien-1-ol, 7-methoxy-3,7-dimethyloctan-2-ol, 6,8-dimethylnonan-2-ol, cis-6-nonen-1-ol, 2,6-nonadien-1-ol, 4-methyl-3-decen-5-ol, benzyl alcohol, 2-methoxy-4-(1-propenyl)phenol, 2-methoxy-4-(2-propenyl)phenol, 4-hydroxy-3-methoxybenzaldehyde, and mixtures thereof.
11 . A compound according to claim 1 having the formula:
wherein OR derives from a fragrance raw material alcohol selected from the group consisting of 4-(1-methylethyl)cyclohexanemethanol, 2,4-dimethyl-3-cyclohexen-1-ylmethanol, 2,4-dimethylcyclohex-1-ylmethanol, 2,4,6-trimethyl-3-cyclohexen-1-ylmethanol, 2-phenylethanol, 1-(4-isopropylcyclohexyl)ethanol, 2-(o-methylphenyl)ethanol, 2-(m-methylphenyl)ethanol, 2-(p-methylphenyl)-ethanol, 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol, 3-phenyl-2-propen-1-ol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, 3-methyl-5-phenylpentan-1-ol, 3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, 2-methyl-4-phenylpentan-1-ol, cis-3-hexen-1-ol, 3,7-dimethyl-6-octen-1-ol, 3,7-dimethyl-2,6-octadien-1-ol, 7-methoxy-3,7-dimethyloctan-2-ol, 6,8-dimethylnonan-2-ol, cis-6-nonen-1-ol, 2,6-nonadien-1-ol, 4-methyl-3-decen-5-ol, benzyl alcohol, 2-methoxy-4-(1-propenyl)phenol, 2-methoxy-4-(2-propenyl)phenol, 4-hydroxy-3-methoxybenzaldehyde, and mixtures thereof.
12 . A compound according to claim 1 wherein R is selected from the group consisting of 1,5-dimethyl-1-vinylhex-4-enyl, 3,7-dimethyloct-7-enyl, 3,7-dimethyloctan-3-yl, and 2-methyl-6-methylene-7-octen-2-yl.
13 . A compound according to claim 1 wherein —OR is derived from a terpene alcohol selected from the group consisting of geraniol, nerol, eugenol, isoeugenol, citronellol, menthol, isopulegol, terpineol, borneol, isoborneol, linalool, tetrahydrolinalool, myrcenol, dihydromyrcenol, muguol, farnesol and mixtures thereof.
14 . A compound according to claim 1 wherein —OR is derived from a non-terpene alcohol selected from the group consisting of cinnamyl alcohol, methylcinnamyl alcohol, Majantol, Hydrotropic alcohol, nopol, Lavandulol, carvenol, cuminyl alcohol, thymol, and mixtures thereof.
15 . A personal care composition having sustained fragrance, said composition comprising:
a) from about 0.001% to about 50% by weight, of a photo-labile pro-fragrance compound having the formula: wherein OR is a unit derived from a fragrance raw material alcohol, HOR; R 1 is one or more electron donating groups; each R 2 is independently hydrogen, C 1 -C 12 alkyl, and mixtures thereof; X is selected from the group consisting of —OH, —NH 2 , —NHR 3 , and mixtures thereof; R 3 is hydrogen, C 1 -C 12 linear or branched alkyl, C 6 -C 10 aryl, and mixtures thereof; b) optionally from about 0.001% to about 50% by weight, of one or more fragrance raw materials; and c) the balance carriers and adjunct ingredients.
16 . A composition according to claim 15 wherein said R 1 is hydroxy, C 1 -C 12 linear or branched alkoxy, and mixtures thereof.
17 . A composition according to claim 16 wherein X is hydroxy and R 1 is hydroxy.
18 . A composition according to claim 17 wherein R 1 is 4-hydroxy.
19 . A composition according to claim 18 wherein R 2 is hydrogen or methyl.
20 . A composition according to claim 15 wherein the photo-labile pro-fragrance has the formula:
wherein OR derives from a fragrance raw material alcohol selected from the group consisting of 4-(1-methylethyl)cyclohexanemethanol, 2,4-dimethyl-3-cyclohexen-1-ylmethanol, 2,4-dimethylcyclohex-1-ylmethanol, 2,4,6-trimethyl-3-cyclohexen-1-ylmethanol, 2-phenylethanol, 1-(4-isopropylcyclohexyl)ethanol, 2-(o-methylphenyl)ethanol, 2-(m-methylphenyl)ethanol, 2-(p-methylphenyl)-ethanol, 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol, 3-phenyl-2-propen-1-ol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, 3-methyl-5-phenylpentan-1-ol, 3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, 2-methyl-4-phenylpentan-1-ol, cis-3-hexen-1-ol, 3,7-dimethyl-6-octen-1-ol, 3,7-dimethyl-2,6-octadien-1-ol, 7-methoxy-3,7-dimethyloctan-2-ol, 6,8-dimethylnonan-2-ol, cis-6-nonen-1-ol, 2,6-nonadien-1-ol, 4-methyl-3-decen-5-ol, benzyl alcohol, 2-methoxy-4-(1-propenyl)phenol, 2-methoxy-4-(2-propenyl)phenol, 4-hydroxy-3-methoxybenzaldehyde, and mixtures thereof.
21 . A composition according to claim 15 wherein the photo-labile pro-fragrance has the formula:
wherein OR derives from a fragrance raw material alcohol selected from the group consisting of 4-(1-methylethyl)cyclohexanemethanol, 2,4-dimethyl-3-cyclohexen-1-ylmethanol, 2,4-dimethylcyclohex-1-ylmethanol, 2,4,6-trimethyl-3-cyclohexen-1-ylmethanol, 2-phenylethanol, 1-(4-isopropylcyclohexyl)ethanol, 2-(o-methylphenyl)ethanol, 2-(m-methylphenyl)ethanol, 2-(p-methylphenyl)-ethanol, 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol, 3-phenyl-2-propen-1-ol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, 3-methyl-5-phenylpentan-1-ol, 3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, 2-methyl-4-phenylpentan-1-ol, cis-3-hexen-1-ol, 3,7-dimethyl-6-octen-1-ol, 3,7-dimethyl-2,6-octadien-1-ol, 7-methoxy-3,7-dimethyloctan-2-ol, 6,8-dimethylnonan-2-ol, cis-6-nonen-1-ol, 2,6-nonadien-1-ol, 4-methyl-3-decen-5-ol, benzyl alcohol, 2-methoxy-4-(1-propenyl)phenol, 2-methoxy-4-(2-propenyl)phenol, 4-hydroxy-3-methoxybenzaldehyde, and mixtures thereof.
22 . A composition according to claim 15 wherein the photo-labile pro-fragrance has the formula:
wherein OR derives from a fragrance raw material alcohol selected from the group consisting of 4-(1-methylethyl)cyclohexanemethanol, 2,4-dimethyl-3-cyclohexen-1-ylmethanol, 2,4-dimethylcyclohex-1-ylmethanol, 2,4,6-trimethyl-3-cyclohexen-1-ylmethanol, 2-phenylethanol, 1-(4-isopropylcyclohexyl)ethanol, 2-(o-methylphenyl)ethanol, 2-(m-methylphenyl)ethanol, 2-(p-methylphenyl)-ethanol, 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol, 3-phenyl-2-propen-1-ol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, 3-methyl-5-phenylpentan-1-ol, 3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, 2-methyl-4-phenylpentan-1-ol, cis-3-hexen-1-ol, 3,7-dimethyl-6-octen-1-ol, 3,7-dimethyl-2,6-octadien-1-ol, 7-methoxy-3,7-dimethyloctan-2-ol, 6,8-dimethylnonan-2-ol, cis-6-nonen-1-ol, 2,6-nonadien-1-ol, 4-methyl-3-decen-5-ol, benzyl alcohol, 2-methoxy-4-(1-propenyl)phenol, 2-methoxy-4-(2-propenyl)phenol, 4-hydroxy-3-methoxybenzaldehyde, and mixtures thereof.
23 . A composition according to claim 15 wherein the photo-labile pro-fragrance has the formula:
wherein OR derives from a fragrance raw material alcohol selected from the group consisting of 4-(1-methylethyl)cyclohexanemethanol, 2,4-dimethyl-3-cyclohexen-1-ylmethanol, 2,4-dimethylcyclohex-1-ylmethanol, 2,4,6-trimethyl-3-cyclohexen-1-ylmethanol, 2-phenylethanol, 1-(4-isopropylcyclohexyl)ethanol, 2-(o-methylphenyl)ethanol, 2-(m-methylphenyl)ethanol, 2-(p-methylphenyl)-ethanol, 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol, 3-phenyl-2-propen-1-ol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, 3-methyl-5-phenylpentan-1-ol, 3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, 2-methyl-4-phenylpentan-1-ol, cis-3-hexen-1-ol, 3,7-dimethyl-6-octen-1-ol, 3,7-dimethyl-2,6-octadien-1-ol, 7-methoxy-3,7-dimethyloctan-2-ol, 6,8-dimethylnonan-2-ol, cis-6-nonen-1-ol, 2,6-nonadien-1-ol, 4-methyl-3-decen-5-ol, benzyl alcohol, 2-methoxy-4-(1-propenyl)phenol, 2-methoxy-4-(2-propenyl)phenol, 4-hydroxy-3-methoxybenzaldehyde, and mixtures thereof.
24 . A composition according to claim 15 wherein R is derived from a terpene alcohol selected from the group consisting of geraniol, nerol, eugenol, isoeugenol, citronellol, menthol, isopulegol, terpineol, borneol, isoborneol, linalool, tetrahydrolinalool, myrcenol, dihydromyrcenol, muguol, farnesol and mixtures thereof.
25 . A composition according to claim 15 wherein R is derived from a non-terpene alcohol selected from the group consisting of cinnamyl alcohol, methylcinnamyl alcohol, Majantol, Hydrotropic alcohol, nopol, Lavandulol, carvenol, cuminyl alcohol, thymol, and mixtures thereof.
26 . A composition according to claim 15 wherein R is derived from a blossom alcohol selected from the group consisting of 4-(1-methylethyl)cyclo-hexanemethanol, 2,4-dimethyl-3-cyclohexen-1-ylmethanol, 2,4-dimethylcyclohex-1-ylmethanol, 2,4,6-trimethyl-3-cyclohexen-1-ylmethanol, 2-phenylethanol, 1-(4-isopropylcyclohexyl)ethanol, 2-(o-methylphenyl)ethanol, 2-(m-methylphenyl)ethanol, 2-(p-methylphenyl)-ethanol, 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol, 3-phenyl-2-propen-1-ol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, 3-methyl-5-phenylpentan-1-ol, 3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, 2-methyl-4-phenylpentan-1-ol, cis-3-hexen-1-ol, 3,7-dimethyl-6-octen-1-o, 3,7-dimethyl-2,6-octadien-1-ol, 7-methoxy-3,7-dimethyloctan-2-ol, 6,8-dimethylnonan-2-ol, cis-6-nonen-1-ol, 2,6-nonadien-1-ol, 4-methyl-3-decen-5-ol, benzyl alcohol, 2-methoxy-4-(1-propenyl)phenol, 2-methoxy-4-(2-propenyl)phenol, 4-hydroxy-3-methoxybenzaldehyde, and mixtures thereof.
27 . A laundry detergent composition comprising:
a) from 0.001% to 10% by weight, of a fragrance delivery system, said system comprising:
i) from about 0.001% to about 100% by weight, of a photo-labile pro-fragrance compound having the formula:
wherein OR is a unit derived from a fragrance raw material alcohol, HOR; R 1 is one or more electron donating groups; each R 2 is independently hydrogen, C 1 -C 12 alkyl, and mixtures thereof; X is selected from the group consisting of —OH, —NH 2 , —NHR 3 , and mixtures thereof; R 3 is hydrogen, C 1 -C 12 linear or branched alkyl, C 6 -C 10 aryl, and mixtures thereof;
ii) optionally from about 0.001% to about 50% by weight, of one or more fragrance raw materials;
b) from about 10% to about 80% by weight, of a surfactant system; and c) the balance carriers and other adjunct ingredients.
28 . A composition according to claim 27 wherein said surfactant system comprises:
i) from 0.01% by weight, of a surfactant selected from the group consisting of alkyl sulfate surfactants, alkoxy sulfate surfactants, mid-chain branched alkyl sulfate surfactants, mid-chain branched alkoxy sulfate surfactants, mid-chain branched aryl sulfonate surfactants, and mixtures thereof;
ii) from 0.01% by weight, of one or more aryl sulphonate anionic surfactants;
iii) from 0.01% by weight, of one or more nonionic surfactants.
29 . A laundry softener composition comprising:
a) from 0.001% to 10% by weight, of a fragrance delivery system, said system comprising:
i) from about 0.001% to about 100% by weight, of a photo-labile pro-fragrance compound having the formula:
wherein OR is a unit derived from a fragrance raw material alcohol, HOR; R 1 is one or more electron donating groups; each R 2 is independently hydrogen, C 1 -C 12 alkyl, and mixtures thereof; X is selected from the group consisting of —OH, —NH 2 , —NHR 3 , and mixtures thereof; R 3 is hydrogen, C 1 -C 12 linear or branched alkyl, C 6 -C 10 aryl, and mixtures thereof;
ii) optionally from about 0.001% to about 50% by weight, of one or more fragrance raw materials;
b) from about 10% to about 80% by weight, of a softener system; and c) the balance carriers and other adjunct ingredients.
30 . A shampoo composition having sustained fragrance, said composition comprising:
a) from about 0.001% to about 50% by weight, of a photo-labile pro-fragrance compound having the formula: wherein OR is a unit derived from a fragrance raw material alcohol, HOR; R 1 is one or more electron donating groups; each R 2 is independently hydrogen, C 1 -C 12 alkyl, and mixtures thereof; X is selected from the group consisting of —OH, —NH 2 , —NHR 3 , and mixtures thereof; R 3 is hydrogen, C 1 -C 12 linear or branched alkyl, C 6 -C 10 aryl, and mixtures thereof; b) optionally from about 0.001% to about 50% by weight, of one or more fragrance raw materials; and c) the balance carriers and adjunct ingredients.Join the waitlist — get patent alerts
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