Novel photostabilizers, uv absorbers, and methods of photostabilizing compositions

A method of protecting a composition from ultraviolet radiation, comprising applying to said composition a compound of formula (I):

• wherein R2 is (a) phenyl substituted with 0, 1, 2, 3, or 4 R6 substituents or (b) 1-naphthyl or 2-naphthyl substituted with 0, 1, 2, 3, or 4 R6 substituents;
• R1 is selected from the group consisting of aryl, and substituted aryl;
• R3 and R4 are the same or different and are selected from the group consisting of C1-C30 alkyl, C3-C8 cycloalkyl, substituted alkyl, substituted cycloalkyl, aryl, heteroaryl, heterocycloalkyl, substituted aryl, substituted heteroaryl, and substituted heterocycloalkyl;
• X is selected from the group consisting of O—C1-C20 alkyl-O—, N(R7)—C1-C20 alkyl-N(R7)—, and S—C1-C20 alkyl-S—;
• R7 is selected from the group consisting of hydrogen and C1-C20 alkyl;
• R5 is a structure of formula (II):
• R9 is (a) phenyl substituted with 0, 1, 2, 3, or 4 R10 substituents or (b) 1-naphthyl or 2-naphthyl substituted with 0, 1, 2, 3, or 4 R10 substituents;
• R6 and R10 are the same or different and are selected from the group consisting of hydrogen, hydroxyl, alkyl, alkenyl, alkynyl, alkoxy, halo, ester, nitro, nitroso, alkylcarbonyl, alkoxycarbonyl, aryl, amino, substituted amino, amido, substituted amido, sulfate, carboxylate, oxycarbonyl, cycloalkyl, haloalkyl, cyano, and thioether;
• R8 is selected from the group consisting of aryl, and substituted aryl;
• and n is an integer from 1 to 500.

A method of photostabilizing a dibenzoylmethane derivative, said method comprising the step of adding to said dibenzoylmethane derivative a photostabilizing amount of a compound of formula (I):

• wherein R2 is (a) phenyl substituted with 0, 1, 2, 3, or 4 R6 substituents or (b) 1-naphthyl or 2-naphthyl substituted with 0, 1, 2, 3, or 4 R6 substituents;
• R1 is selected from the group consisting of hydrogen, C1-C50 alkyl, C2-C50 alkenyl, C2-C50 alkynyl, C3-C8 cycloalkyl, C2-C7 heterocycloalkyl, aryl, C1-C50 polyether, C1-C50 substituted alkyl, C3-C8 substituted cycloalkyl, C2-C50 substituted alkenyl, C2-C50 substituted alkynyl, C2-C7 substituted heterocycloalkyl, substituted aryl, heteroaryl, and substituted heteroaryl;
• R3 and R4 are the same or different and are selected from the group consisting of C1-C30 alkyl, C3-C8 cycloalkyl, substituted alkyl, substituted cycloalkyl, aryl, heteroaryl, heterocycloalkyl, substituted aryl, substituted heteroaryl, and substituted heterocycloalkyl;
• X is selected from the group consisting of O—C1-C20 alkyl-O—, N(R7)—C1-C20 alky-N(R7)—, and S—C1-C20 alkyl-S—;
• R7 is selected from the group consisting of hydrogen and C1-C20 alkyl;
• R5 is selected from the group consisting of C3-C50 alkyl, C2-C50 alkenyl, C2-C50 alkynyl, C3-C8 cycloalkyl, C2-C7 heterocycloalkyl, aryl, C1-C50 polyether, C1-C50 substituted alkyl, C3-C8 substituted cycloalkyl, C2-C50 substituted alkenyl, C2-C50 substituted alkynyl, C2-C7 substituted heterocycloalkyl, substituted aryl, heteroaryl, substituted heteroaryl, and a structure of formula (II):
• R9 is (a) phenyl substituted with 0, 1, 2, 3, or 4 R10 substituents or (b) 1-naphthyl or 2-naphthyl substituted with 0, 1, 2, 3, or 4 R10 substituents;
• R6 and R10 are the same or different and are selected from the group consisting of hydrogen, hydroxyl, alkyl, alkenyl, alkynyl, alkoxy, halo, ester, nitro, nitroso, alkylcarbonyl, alkoxycarbonyl, aryl, amino, substituted amino, amido, substituted amido, sulfate, carboxylate, oxycarbonyl, cycloalkyl, haloalkyl, cyano, and thioether;
• R8 is selected from the group consisting of hydrogen, C2-C50 alkyl, C2-C50 alkenyl, C2-C50 alkynyl, C3-C8 cycloalkyl, C2-C7 heterocycloalkyl, aryl, C1-C50 polyether, C1-C50 substituted alkyl, C3-C8 substituted cycloalkyl, C2-C50 substituted alkenyl, C2-C50 substituted alkynyl, C2-C7 substituted heterocycloalkyl, substituted aryl, heteroaryl, and substituted heteroaryl;
• and n is an integer from 1 to 500.

A method of quenching triplet excited state energy from a triplet-excited photoactive compound in a sunscreen composition comprising adding to said composition a compound of formula (I):

• wherein R2 is (a) phenyl substituted with 0, 1, 2, 3, or 4 R6 substituents or (b) 1-naphthyl or 2-naphthyl substituted with 0, 1, 2, 3, or 4 R6 substituents;
• R1 is selected from the group consisting of hydrogen, C1-C50 alkyl, C2-C50 alkenyl, C2-C50 alkynyl, C3-C8 cycloalkyl, C2-C7 heterocycloalkyl, aryl, C1-C50 polyether, C1-C50 substituted alkyl, C3-C8 substituted cycloalkyl, C2-C50 substituted alkenyl, C2-C50 substituted alkynyl, C2-C7 substituted heterocycloalkyl, substituted aryl, heteroaryl, and substituted heteroaryl;
• R3 and R4 are the same or different and are selected from the group consisting of C1-C30 alkyl, C3-C8 cycloalkyl, substituted alkyl, substituted cycloalkyl, aryl, heteroaryl, heterocycloalkyl, substituted aryl, substituted heteroaryl, and substituted heterocycloalkyl;
• X is selected from the group consisting of O—C1-C20 alkyl-O—, N(R7)—C1-C20 alky-N(R7)—, and S—C1-C20 alkyl-S—;
• R7 is selected from the group consisting of hydrogen and C1-C20 alkyl;
• R5 is selected from the group consisting of C3-C50 alkyl, C2-C50 alkenyl, C2-C50 alkynyl, C3-C8 cycloalkyl, C2-C7 heterocycloalkyl, aryl, C1-C50 polyether, C1-C50 substituted alkyl, C3-C8 substituted cycloalkyl, C2-C50 substituted alkenyl, C2-C50 substituted alkynyl, C2-C7 substituted heterocycloalkyl, substituted aryl, heteroaryl, substituted heteroaryl, and a structure of formula (II):
• R9 is (a) phenyl substituted with 0, 1, 2, 3, or 4 R10 substituents or (b) 1-naphthyl or 2-naphthyl substituted with 0, 1, 2, 3, or 4 R10 substituents;
• R6 and R10 are the same or different and are selected from the group consisting of hydrogen, hydroxyl, alkyl, alkenyl, alkynyl, alkoxy, halo, ester, nitro, nitroso, alkylcarbonyl, alkoxycarbonyl, aryl, amino, substituted amino, amido, substituted amido, sulfate, carboxylate, oxycarbonyl, cycloalkyl, haloalkyl, cyano, and thioether;
• R8 is selected from the group consisting of hydrogen, C2-C50 alkyl, C2-C50 alkenyl, C2-C50 alkynyl, C3-C8 cycloalkyl, C2-C7 heterocycloalkyl, aryl, C1-C50 polyether, C1-C50 substituted alkyl, C3-C8 substituted cycloalkyl, C2-C50 substituted alkenyl, C2-C50 substituted alkynyl, C2-C7 substituted heterocycloalkyl, substituted aryl, heteroaryl, and substituted heteroaryl;
• and n is an integer from 1 to 500.

A method for increasing the UV-A Protection Value of a composition containing at least one photoactive compound comprising adding a compound of formula (I) to said composition in an amount sufficient to increase the UV-A Protection Value of said composition:

• wherein R2 is (a) phenyl substituted with 0, 1, 2, 3, or 4 R6 substituents or (b) 1-naphthyl or 2-naphthyl substituted with 0, 1, 2, 3, or 4 R6 substituents;
• R1 is selected from the group consisting of hydrogen, C1-C50 alkyl, C2-C50 alkenyl, C2-C50 alkynyl, C3-C8 cycloalkyl, C2-C7 heterocycloalkyl, aryl, C1-C50 polyether, C1-C50 substituted alkyl, C3-C8 substituted cycloalkyl, C2-C50 substituted alkenyl, C2-C50 substituted alkynyl, C2-C7 substituted heterocycloalkyl, substituted aryl, heteroaryl, and substituted heteroaryl;
• R3 and R4 are the same or different and are selected from the group consisting of C1-C30 alkyl, C3-C8 cycloalkyl, substituted alkyl, substituted cycloalkyl, aryl, heteroaryl, heterocycloalkyl, substituted aryl, substituted heteroaryl, and substituted heterocycloalkyl;
• X is selected from the group consisting of O—C1-C20 alkyl-O—, N(R7)—C1-C20 alky-N(R7)—, and S—C1-C20 alkyl-S—;
• R7 is selected from the group consisting of hydrogen and C1-C20 alkyl;
• R5 is selected from the group consisting of C3-C50 alkyl, C2-C50 alkenyl, C2-C50 alkynyl, C3-C8 cycloalkyl, C2-C7 heterocycloalkyl, aryl, C1-C50 polyether, C1-C50 substituted alkyl, C3-C8 substituted cycloalkyl, C2-C50 substituted alkenyl, C2-C50 substituted alkynyl, C2-C7 substituted heterocycloalkyl, substituted aryl, heteroaryl, substituted heteroaryl, and a structure of formula (II):
• R9 is (a) phenyl substituted with 0, 1, 2, 3, or 4 R10 substituents or (b) 1-naphthyl or 2-naphthyl substituted with 0, 1, 2, 3, or 4 R10 substituents;
• R6 and R10 are the same or different and are selected from the group consisting of hydrogen, hydroxyl, alkyl, alkenyl, alkynyl, alkoxy, halo, ester, nitro, nitroso, alkylcarbonyl, alkoxycarbonyl, aryl, amino, substituted amino, amido, substituted amido, sulfate, carboxylate, oxycarbonyl, cycloalkyl, haloalkyl, cyano, and thioether;
• R8 is selected from the group consisting of hydrogen, C2-C50 alkyl, C2-C50 alkenyl, C2-C50 alkynyl, C3-C8 cycloalkyl, C2-C7 heterocycloalkyl, aryl, C1-C50 polyether, C1-C50 substituted alkyl, C3-C8 substituted cycloalkyl, C2-C50 substituted alkenyl, C2-C50 substituted alkynyl, C2-C7 substituted heterocycloalkyl, substituted aryl, heteroaryl, and substituted heteroaryl;
• and n is an integer from 1 to 500.

A method of photostabilizing a photoactive compound, said method comprising the step of adding to said photoactive compound a photostabilizing amount of a compound of formula (III):

• wherein R1 and R8 are the same or different and are selected from the group consisting of hydrogen, C1-C50 alkyl, C2-C50 alkenyl, C2-C50 alkynyl, C3-C8 cycloalkyl, C2-C7 heterocycloalkyl, aryl, C1-C50 polyether, C1-C50 substituted alkyl, C3-C8 substituted cycloalkyl, C2-C50 substituted alkenyl, C2-C50 substituted alkynyl, C2-C7 substituted heterocycloalkyl, substituted aryl, heteroaryl, and substituted heteroaryl;
• R3 and R4 are the same or different and are selected from the group consisting of C1-C30 alkyl, C3-C8 cycloalkyl, substituted alkyl, substituted cycloalkyl, aryl, heteroaryl, heterocycloalkyl, substituted aryl, substituted heteroaryl, and substituted heterocycloalkyl;
• X is selected from the group consisting of O—C1-C20 alkyl-O—, N(R7)—C1-C20 alkyl-N(R7)—, and S—C1-C20 alkyl-S—;
• R7 is selected from the group consisting of hydrogen and C1-C20 alkyl;
• R9 and R10 are the same or different and are each electron donating groups;
• and n is an integer from 1 to 500.

A sunscreen composition, comprising a mixture of a photoactive compound, and a compound of formula (III):

• wherein R1 and R8 are the same or different and are selected from the group consisting of hydrogen, C1-C50 alkyl, C2-C50 alkenyl, C2-C50 alkynyl, C3-C8 cycloalkyl, C2-C7 heterocycloalkyl, aryl, C1-C50 polyether, C1-C50 substituted alkyl, C3-C8 substituted cycloalkyl, C2-C50 substituted alkenyl, C2-C50 substituted alkynyl, C2-C7 substituted heterocycloalkyl, substituted aryl, heteroaryl, and substituted heteroaryl;
• R3 and R4 are the same or different and are selected from the group consisting of C1-C30 alkyl, C3-C8 cycloalkyl, substituted alkyl, substituted cycloalkyl, aryl, heteroaryl, heterocycloalkyl, substituted aryl, substituted heteroaryl, and substituted heterocycloalkyl;
• X is selected from the group consisting of O—C1-C20 alkyl-O—, N(R7)—C1-C20 alkyl-N(R7)—, and S—C1-C20 alkyl-S—;
• R7 is selected from the group consisting of hydrogen and C1-C20 alkyl;
• R9 and R10 are the same or different and are each electron donating groups;
• and n is an integer from 1 to 500.

A method of protecting a surface from ultraviolet radiation, comprising topically applying to said surface, in a carrier, a compound of formula (III):

• wherein R1 and R8 are the same or different and are selected from the group consisting of hydrogen, C1-C50 alkyl, C2-C50 alkenyl, C2-C50 alkynyl, C3-C8 cycloalkyl, C2-C7 heterocycloalkyl, aryl, C1-C50 polyether, C1-C50 substituted alkyl, C3-C8 substituted cycloalkyl, C2-C50 substituted alkenyl, C2-C50 substituted alkynyl, C2-C7 substituted heterocycloalkyl, substituted aryl, heteroaryl, and substituted heteroaryl;
• R3 and R4 are the same or different and are selected from the group consisting of C1-C30 alkyl, C3-C8 cycloalkyl, substituted alkyl, substituted cycloalkyl, aryl, heteroaryl, heterocycloalkyl, substituted aryl, substituted heteroaryl, and substituted heterocycloalkyl;
• X is selected from the group consisting of O—C1-C20 alkyl-O—, N(R7)—C1-C20 alkyl-N(R7)—, and S—C1-C20 alkyl-S—;
• R7 is selected from the group consisting of hydrogen and C1-C20 alkyl;
• R9 and R10 are the same or different and are each electron donating groups;
• and n is an integer from 1 to 500.