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US 6,280,711 B1Granted
Photoresponsive sunscreen compositions
AssigneeCalifornia Institute of Technology
InventorsRonald S. Rock, Michael H. B. Stowell
Life of this patent
Estimating the term…
Abstract
The disclosure provides sunscreen compositions comprising a carrier for topical administration and photoresponsive first sunscreen agents which are capable of undergoing intramolecular photorearrangements to form second sunscreen agents. The second sunscreen agents absorb more ultraviolet radiation than the first sunscreen agents. The sunscreen composition may comprise the prephotorearrangement first sunscreen agent, the photorearranged second sunscreen agent, a combination of the first and second sunscreen agents, or any of the above in combination with a known sunscreen agent.
Claims13
A composition for variably blocking radiation comprising:
- (A) a first organic sunscreen agent that undergoes an intramolecular photochemical rearrangement that is induced by ultraviolet radiation to form a second sunscreen agent wherein the second sunscreen agent can absorb more ultraviolet radiation per molecule than the first sunscreen agent;
- and
- (B) a carrier for topical administration.
A sunscreen composition comprising:
- (A) a compound having the formula
- wherein
- R1 is hydroxy, carbonate, substituted ester (—OC(O)R12), phosphorus-containing group, a sulfur-containing group, or a fluorescent label;
- R2 is hydrogen, hydroxy, alkyl, aryl, alkoxy or substituted alkoxy;
- R3 is hydrogen, hydroxy, alkyl, aryl, alkoxy or substituted alkoxy;
- R4 is hydrogen, hydroxy, alkyl, aryl, alkoxy or substituted alkoxy;
- R5 is hydrogen, hydroxy, alkyl, aryl, alkoxy or substituted alkoxy;
- R6 is hydrogen, hydroxy, alkyl, aryl, alkoxy or substituted alkoxy;
- R7 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy;
- R8 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy;
- R9 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy;
- R10 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy;
- R11 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy;
- R12, if present, is hydrogen, alkyl, aryl, amine, secondary alkyl amine, tertiary alkyl amine, alkoxy, a fluorescent label, or a biomolecule;
- wherein at least one of R2 or R6 is hydrogen;
- wherein at least one of R2, R3, R4, R5, or R6 is hydroxy or substituted alkoxy;
- and
- (B) a carrier for topical administration.
15 more elements
A sunscreen composition comprising:
- (A) an ultraviolet-absorbing compound having the formula
- wherein
- R2 is hydrogen, hydroxy (C1-201)alkyl, (C5-12)aryl, (C1-20)alkoxy or substituted (C1-20)alkoxy;
- R3 is hydrogen, hydroxy, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy or substituted (C1-20)alkoxy;
- R4 is hydrogen, hydroxy, (C1-20)alkyl, (C ,5-21)aryl, (C1-20)alkoxy or substituted (C1-20)alkoxy;
- R5 is hydrogen, hydroxy, (C1-20)alkyl, (C5-12)aryl, (C1-201)alkoxy or substituted (C1-20)alkoxy;
- R7 is hydrogen, (C1-20)alkyl, C5-12aryl, C1-201)alkoxy or substituted (C1-20)alkoxy;
- R8 is hydrogen, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy or substituted (C1-20)alkoxy;
- R9 is hydrogen, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy or substituted (C1-20)alkoxy;
- R10 is hydrogen, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy or substituted (C1-20)alkoxy;
- R11 is hydrogen, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy or substituted (C1-20)alkoxy;
- wherein at least one of R2, R3, R4, or R5 is hydroxy or substituted (C1-20)alkoxy;
- and
- (B) a carrier for topical administration.
11 more elements
A composition useful for blocking ultraviolet radiation comprising:
- (A) a compound having the formula
- wherein
- R1 is selected from the group consisting of carbonate, carboxyl, phosphate, pyrophosphate, substituted phosphate (—OP(O)(OR19)(OR20), phosphines, phosphonates, substituted ester (—OC(O)R12) thiol, sulfide, sulfoxide, sulfone, sulfonic acid, sulfate, amine salt (—N(R)3+), and halide;
- R2 is selected from the group consisting of hydrogen, hydroxy, alkyl, aryl, alkoxy, and substituted alkoxy;
- R3 is selected from the group consisting of hydrogen, hydroxy, alkyl, aryl, alkoxy, and substituted alkoxy;
- R4 is selected from the group consisting of hydrogen, hydroxy alkyl, aryl, alkoxy, and substituted alkoxy;
- R5 is selected from the group consisting of hydrogen, hydroxy, alkyl, aryl, alkoxy, and substituted alkoxy;
- R6 is selected from the group consisting of hydrogen, hydroxy, alkyl, aryl, alkoxy, and substituted alkoxy;
- R7 is selected from the group consisting of hydrogen, alkyl, aryl, alkoxy, and substituted alkoxy;
- R8 is selected from the group consisting of hydrogen, alkyl, aryl, alkoxy, and substituted alkoxy;
- R9 is selected from the group consisting of hydrogen, alkyl, aryl, alkoxy, and substituted alkoxy;
- R10 is selected from the group consisting of hydrogen, alkyl, aryl, alkoxy, and substituted alkoxy;
- R11 is selected from the group consisting of hydrogen, alkyl, aryl, alkoxy, and substituted alkoxy;
- R12, if present, is hydrogen, alkyl, aryl, amine, secondary alkyl amine, tertiary alkyl amine, alkoxy, a fluorescent label or a biomolecule;
- R19 is hydrogen, alkyl or aryl;
- R20 is hydrogen, alkyl, or aryl;
- and
- wherein at least one of R2 or R6 is hydrogen;
- wherein at least one of R2, R3, R4, R5 or R6 is hydroxy or substituted alkoxy;
- and
- (B) a carrier for topical administration.
18 more elements
A composition useful for blocking ultraviolet radiation comprising:
- (A) an ultraviolet-absorbing compound having the formula
- wherein
- R2 is selected from the group consisting of hydrogen, hydroxy, (C1-201)alkyl, (C5-12)aryl, (C1-20)alkoxy, and substituted (C1-20)alkoxy;
- R3 is selected from the group consisting of hydrogen, hydroxy, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy, and substituted (C1-20)alkoxy;
- R4 is selected from the group consisting of hydrogen, hydroxy, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy, and substituted (C1-201)alkoxy;
- R5 is selected from the group consisting of hydrogen, hydroxy, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy, and substituted (C1-20)alkoxy;
- R7 is selected from the group consisting of hydrogen, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy, and substituted (C1-20)alkoxy;
- R8 is selected from the group consisting of hydrogen, (C1-20)alkyl, C5-12)aryl, (C1-20)alkoxy, and substituted (C1-20)alkoxy;
- R9 is selected from the group consisting of hydrogen, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy, and substituted (C1-20)alkoxy;
- R10 is selected from the group consisting of hydrogen, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy, and substituted (C1-20)alkoxy;
- R11 is selected from the group consisting of hydrogen, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy, and substituted (C1-20)alkoxy;
- wherein at least one of R2, R3, R4, or R5 is hydroxy or substituted (C1-20)alkoxy and
- (B) a carrier for topical administration.
10 more elements
A sunscreen composition comprising:
- (A) a compound having the formula
- wherein
- R1 is hydroxy, carbonate, substituted ester (—OC(O)R12), phosphorus-containing group, a sulfur-containing group, a fluorescent label, or a biomolecule;
- R2 is hydrogen, hydroxy, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy or substituted (C1-20)alkoxy;
- R3 is hydrogen, hydroxy, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy or substituted (C1-20)alkoxy;
- R4 is hydrogen, hydroxy, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy or substituted (C1-20)alkoxy;
- R5 is hydrogen, hydroxy, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy or substituted (C1-20)alkoxy;
- R6 is hydrogen, hydroxy, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy or substituted (C1-20)alkoxy;
- R7 is hydrogen, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy or substituted (C1-20)alkoxy;
- R8 is hydrogen, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy or substituted (C1-20)alkoxy;
- R9 is hydrogen, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy or substituted (C1-20)alkoxy;
- R10 is hydrogen, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy or substituted (C1-20)alkoxy;
- R11 is hydrogen, (C 1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy or substituted (C1-20)alkoxy;
- R12, if present, is hydrogen, (C1-20)alkyl, (C5-12)aryl, amine, secondary (C1-20)alkyl amine, tertiary (C1-20)alkyl amine, (C1-20)alkoxy, a fluorescent label, or a biomolecule;
- wherein at least one of R2 or R6 is hydrogen;
- wherein at least one of R2, R3, R4, R5, or R6 is hydroxy or substituted (C1-20)alkoxy;
- and
- (B) a carrier for topical administration.
15 more elements
A composition useful for blocking ultraviolet radiation comprising:
- (A) a compound having the formula
- wherein
- R1 is selected from the group consisting of carbonate, carboxyl, phosphate, pyrophosphate, substituted phosphate (—OP(O)(OR19)(OR20), phosphines, phosphonates, substituted ester (—OC(O)R12) thiol, sulfide, sulfoxide, sulfone, sulfonic acid, sulfate, amine salt (—N(R)3+), and halide;
- R2 is selected from the group consisting of hydrogen, hydroxy, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy, and substituted (C1-20)alkoxy;
- R3 is selected from the group consisting of hydrogen, hydroxy, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy, and substituted (C1-20)alkoxy;
- R4 is selected from the group consisting of hydrogen, hydroxy, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy, and substituted (C1-20)alkoxy;
- R5 is selected from the group consisting of hydrogen, hydroxy, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy, and substituted (C1-20)alkoxy;
- R6 is selected from the group consisting of hydrogen, hydroxy, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy, and substituted (C1-20)alkoxy;
- R7 is selected from the group consisting of hydrogen, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy, and substituted (C1-20)alkoxy;
- R8 is selected from the group consisting of hydrogen, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy, and substituted (C1-20)alkoxy;
- R9 is selected from the group consisting of hydrogen, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy, and substituted (C1-20)alkoxy;
- R10 is selected from the group consisting of hydrogen, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy, and substituted (C1-20)alkoxy;
- R11 is selected from the group consisting of hydrogen, (C1-20)alkyl, (C5-12)aryl, (C1-20)alkoxy, and substituted (C1-20)alkoxy;
- R12, if present, is hydrogen, (C1-20)alkyl, (C5-12)aryl, amine, secondary (C1-20)alkyl amine, tertiary (C1-20)alkyl amine, (C1-20)alkoxy, a fluorescent label, or a biomolecule;
- R19 is hydrogen, (C1-20)alkyl or (C5-12)aryl;
- R20 is hydrogen, (C1-20)alkyl, or (C5-12)aryl;
- and
- wherein at least one of R2 or R6 is hydrogen;
- wherein at least one of R2, R3, R4, R5 or R6 is hydroxy or substituted (C1-20)alkoxy;
- and
- (B) a carrier for topical administration.
18 more elements
A sunscreen composition comprising:
- (A) a compound having the formula
- wherein
- R1 is a biomolecule;
- R2 is hydrogen, hydroxy, alkyl, aryl, alkoxy or substituted alkoxy;
- R3 is hydrogen, hydroxy, alkyl, aryl, alkoxy or substituted alkoxy;
- R4 is hydrogen, hydroxy, alkyl, aryl, alkoxy or substituted alkoxy;
- R5 is hydrogen, hydroxy, alkyl, aryl, alkoxy or substituted alkoxy;
- R6 is hydrogen, hydroxy, alkyl, aryl, alkoxy or substituted alkoxy;
- R7 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy;
- R8 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy;
- R9 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy;
- R10 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy;
- R11 is hydrogen, alkyl, aryl, alkoxy or substituted alkoxy;
- wherein at least one of R2 or R6 is hydrogen;
- wherein at least one of R2, R3, R4, R5, or R6 is hydroxy or substituted alkoxy;
- and
- (B) a carrier for topical administration.
14 more elements
Dependencies are inferred from the claim text.