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US 7,118,760 B2Granted
Esters of aryl benzimidazole sulfonic acids and sunscreen compositions containing same
AssigneeAvon Products, Inc.
InventorsAnthony D. Gonzalez, Andrew H. Pechko, Glen T. Anderson, Robert E. Kalafsky, Michael V. Lowenborg
Life of this patent
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Abstract
The present invention provides novel aryl benzimidazole sulfonic acid esters and cosmetic compositions that employ the novel aryl benzimidazole sulfonic acid esters as sunscreens. The cosmetic compositions can be water, organic solvent or emulsion based. Also provided are methods of using the compositions to protect skin from exposure to the sun, and optionally, repel insects.
Claims29
A sunscreen selected from the group consisting of compounds represented by the formula:
- and
- (d) any mixtures thereof;
- wherein each R is independently selected from the group consisting of a linear, branched or cyclic C16 to C50 alkyl;
- a linear, branched or cyclic C16 to C50 alkyl interrupted, substituted, or interrupted and substituted by one or more groups each independently selected from the group consisting of aryl, heteroaryl, O, S, SO, SO2, CO, COO, halogen, cyano, ester, ether, keto, hydroxy, alkoxy, aryloxy, amino, amido, —[O(Si(R10)2]n—, and R10[Si(R10)2]n—;
- a C6 to C24 aryl;
- a C6 to C24 aryl substituted by one or more groups each independently selected from the group consisting of aryl, heteroaryl, O, S, SO, SO2, CO, COO, halogen, cyano, ester, ether, keto, hydroxy, alkoxy, aryloxy, amino, amido, and R10[Si(R10)2]n—;
- a C4 to C24 heteroaryl;
- a C4 to C24 heteroaryl substituted by one or more groups each independently selected from the group consisting of halogen, cyano, ester, ether, keto, hydroxy, alkoxy, aryloxy, amino, amido, and R10[Si(R10)2]n—;
- R10[Si(R10)2]n—;
- and R11 which is a silicone residue derived from a silicone represented by the formula R11OH having a molecular weight up to about 30,000;
- each R1, R2, R3, R4, R5, R7, R8 and R9 is independently selected from the group consisting of hydrogen, halogen, cyano, ester, ether, keto, hydroxy, alkoxy, aryloxy, amino, amido, a linear, branched or cyclic alkyl of 1–12 carbon atoms, a substituted linear, branched or cyclic alkyl of 1–12 carbon atoms, an aryl of 5–12 carbon atoms, a substituted aryl of 5–12 carbon atoms, a heteroaryl of 4–12 carbon atoms, and a substituted heteroaryl of 4–12 carbon atoms;
- wherein each substituent in the substituted alkyl, substituted aryl and substituted heteroaryl groups is independently selected from the group consisting of aryl, heteroaryl, halogen, cyano, ester, ether, keto, hydroxy, alkoxy, aryloxy, amino, and amido;
- each R6 is independently selected from the group consisting of hydrogen, an alkyl of 1–12 carbon atoms, and a substituted alkyl of 1–12 carbon atoms;
- each R10 is independently selected from the group consisting of alkyl, alkoxy, aryl and aryloxy;
- and
- n is from 1 to about 500.
13 more elements
A cosmetic composition comprising:
- a cosmetically acceptable vehicle;
- and
- an effective amount of a sunscreen selected from the group consisting of compounds represented by the formula:
- and
- (d) any mixtures thereof;
- wherein each R is independently selected from the group consisting of a linear, branched or cyclic C16 to C50 alkyl;
- a linear, branched or cyclic C16 to C50 alkyl interrupted, substituted, or interrupted and substituted by one or more groups each independently selected from the group consisting of aryl, heteroaryl, O, S, SO, SO2, CO, COO, halogen, cyano, ester, ether, keto, hydroxy, alkoxy, aryloxy, amino, amido, —[O(Si(R10)2]n—, and R10[Si(R10)2]n—;
- a C6 to C24 aryl;
- a C6 to C24 aryl substituted by one or more groups each independently selected from the group consisting of aryl, heteroaryl, O, S, SO, SO2, CO, COO, halogen, cyano, ester, ether, keto, hydroxy, alkoxy, aryloxy, amino, amido, and R10[Si(R10)2]n—;
- a C4 to C24 heteroaryl;
- a C4 to C24 heteroaryl substituted by one or more groups each independently selected from the group consisting of halogen, cyano, ester, ether, keto, hydroxy, alkoxy, aryloxy, amino, amido, and R10[Si(R10)2]n—;
- R10[Si(R10)2]n—;
- and R11 which is a silicone residue derived from a silicone represented by the formula R11OH having a molecular weight up to about 30,000;
- each R1, R2, R3, R4, R5, R7, R8 and R9 is independently selected from the group consisting of hydrogen, halogen, cyano, ester, ether, keto, hydroxy, alkoxy, aryloxy, amino, amido, a linear, branched or cyclic alkyl of 1–12 carbon atoms, a substituted linear, branched or cyclic alkyl of 1–12 carbon atoms, an aryl of 5–12 carbon atoms, a substituted aryl of 5–12 carbon atoms, a heteroaryl of 4–12 carbon atoms, and a substituted heteroaryl of 4–12 carbon atoms;
- wherein each substituent in the substituted alkyl, substituted aryl and substituted heteroaryl groups is independently selected from the group consisting of aryl, heteroaryl, halogen, cyano, ester, ether, keto, hydroxy, alkoxy, aryloxy, amino, and amido;
- each R6 is independently selected from the group consisting of hydrogen, an alkyl of 1–12 carbon atoms, and a substituted alkyl of 1–12 carbon atoms;
- each R10 is independently selected from the group consisting of alkyl, alkoxy, aryl and aryloxy;
- and
- n is from 1 to about 500.
16 more elements
Dependencies are inferred from the claim text.