Enhancing photostability of thiopyridinone compound without the use of UV filters
The instant disclosure relates to cosmetic compositions and methods of using the cosmetic compositions to benefit the skin. The cosmetic compositions typically include: (a) compounds of thiopyridinone type; (b) and one or more UV boosters. The compositions provide multiple benefits to skin. For example, the compositions are particularly useful for whitening the skin, and for improving skin's appearance.
1 . A cosmetic composition comprising:
i) at least one thiopyridinone compound selected from a compound of formula (I) and a compound of formula (I′), or a salt, optical isomer, racemate, or solvate thereof, and mixtures thereof:
wherein:
R 1 is selected from:
a hydrogen atom; or
a linear C 1 -C 10 alkyl group or a branched C 3 -C 10 alkyl group, each of which is optionally substituted with one or more groups independently selected from —OR 3 and —SR 3 ;
R 2 is selected from:
a hydrogen atom;
a linear C 1 -C 12 alkyl group, a branched C 3 -C 12 alkyl group, or a C 3 -C 8 cycloalkyl group, each of which is optionally substituted with one or more groups independently selected from —OR 3 , —SR 3 , —C(O)OR 3 , and a C 5 -C 12 aryl group optionally substituted with one or more groups independently selected from OH and C 1 -C 8 alkoxy; or
a C 5 -C 12 aryl group optionally substituted with one or more groups independently selected from OH and C 1 -C 8 alkoxy;
R 3 is selected from:
a hydrogen atom; or
a linear C 1 -C 10 alkyl group or a branched C 3 -C 10 alkyl group;
ii) one or more UV boosters selected from the group consisting of ethylhexyl methoxycrylene, diethyl syringylidenemalonate, and mixtures thereof, and
iii) 0 wt. % UV filters;
wherein the weight percentages are based on the total weight of the cosmetic composition; and wherein the association of the one or more UV boosters improves the photostability of the at least one thiopyridinone compound.
2 . The composition of claim 1 , wherein R 1 is a hydrogen atom, a linear C 1 -C 10 alkyl group, or a branched C 3 -C 10 alkyl group.
3 . The composition of claim 1 , wherein R 2 is a hydrogen atom, a linear C 1 -C 10 alkyl group, or a branched C 3 -C 10 alkyl group.
4 . The composition of claim 1 , wherein R 2 is a linear C 1 -C 10 alkyl group, or a branched C 3 -C 10 alkyl group.
5 . The composition of claim 1 , wherein R 2 is a C 3 -C 8 cycloalkyl group or a C 5 -C 12 aryl group optionally substituted with one or more groups independently selected from OH and C 1 -C 8 alkoxy.
6 . The composition of claim 1 , wherein:
R 1 is selected from:
a hydrogen atom; or
a linear C 1 -C 6 alkyl group or a branched C 3 -C 6 alkyl group, each of which is optionally substituted with one or more groups independently selected from —OR 3 and —SR 3 ;
R 2 is selected from:
a hydrogen atom;
a linear C 1 -C 10 alkyl group, a branched C 3 -C 10 alkyl group, or a C 3 -C 8 cycloalkyl group, each of which is optionally substituted with one or more groups independently selected from —OR 3 , —SR 3 , —C(O)OR 3 , and a phenyl group optionally substituted with one or more groups independently selected from OH and C 1 -C 8 alkoxy; and
R 3 is selected from:
a hydrogen atom; or
a linear C 1 -C 6 alkyl group or a branched C 3 -C 6 alkyl group.
7 . The composition of claim 1 , wherein the one or more thiopyridinone compounds of formula (I) and formula (I′) are selected from the group consisting of compounds 1 to 24, or a salt, optical isomer, racemate, or solvate thereof, and mixtures thereof
No.
Structure
Chemical name
1
N-ethyl-2-thioxo-1,2-dihydropyridine- 3-carboxamide
2
N-methyl-2-thioxo-1,2- dihydropyridine-3-carboxamide
3
N-octyl-2-thioxo-1,2-dihydropyridine- 3-carboxamide
4
N-benzyl-2-thioxo-1,2- dihydropyridine-3-carboxamide
5
N-phenyl-2-thioxo-1,2- dihydropyridine-3-carboxamide
6
N-cyclohexyl-2-thioxo-1,2- dihydropyridine-3-carboxamide
7
N-[2-(4-methoxyphenyl)ethyl]-2- thioxo-1,2-dihydropyridine-3- carboxamide
8
N-(2-methylpropyl)-2-thioxo-1,2- dihydropyridine-3-carboxamide
9
N-penty1-2-thioxo-1,2- dihydropyridine-3-carboxamide
10
N-nonyl-2-thioxo-1,2- dihydropyridine-3-carboxamide
11
N-(2-hydroxyethyl)-2-thioxo-1,2- dihydropyridine-3-carboxamide
12
N,N-diethyl 2-mercaptonicotinamide
13
N-ethyl-N-(2-hydroxyethyl)-2-thioxo- 1,2-dihydropyridine-3-carboxamide
14
N-(2,3-dihydroxypropyl)-2-thioxo-1,2- dihydropyridine-3-carboxamide
15
N-(1,3-dihydroxypropan-2-yl)-2- thioxo-1,2-dihydropyridine-3- carboxamide
16
Ethyl N-[(2-thioxo-1,2- dihydropyridin-3- yl)carbonyl]alaninate
17
Ethyl N-[(2-thioxo-1,2- dihydropyridin-3-yl)carbonyl]phenyl alaninate
18
Ethyl N-methyl-N-[(2-thioxo-1,2- dihydropyridin-3- yl)carbonyl]glycinate
19
Ethyl N-[(2-thioxo-1,2- dihydropyridin-3- yl)carbonyl]glycinate
20
N-[(2-thioxo-1,2-dihydropyridin-3- yl)carbonyl]glycine
21
N-methyl-N-[(2-thioxo-1,2- dihydropyridin-3-yl)carbonyl]glycine
22
N,N-bis(2-hydroxyethyl)-2-thioxo-1,2- dihydropyridine-3-carboxamide
23
N-(3-methoxypropyl)-2-thioxo-1,2- dihydropyridine-3-carboxamide
24
N-butyl-2-thioxo-1,2-dihydropyridine- 3-carboxamide.
8 . The composition of claim 1 , wherein the one or more UV boosters are present in an amount ranging from about 0.01 to about 10 wt. %, based on the total weight of the cosmetic composition.
9 . The composition of claim 1 , wherein compound i) is present in an amount ranging from about 0.01 to about 10 wt. %, based on the total weight of the cosmetic composition.
10 . The composition of claim 1 , wherein ethylhexyl methoxycrylene is present in an amount ranging from about 0.2 to about 3 wt. %, based on the total weight of the cosmetic composition.
11 . The composition of claim 1 , wherein diethyl syringylidenemalonate is present in an amount ranging from about 0.2 to about 3 wt. %, based on the total weight of the cosmetic composition.
12 . The composition of claim 1 , wherein the pH is from about 4.5 to about 6.5.
13 . A cosmetic composition comprising:
i) from about 0.01 to about 10 wt. % of at least one thiopyridinone compound selected from a compound of formula (I) and a compound of formula (I′), or an optical isomer, racemate, or solvate thereof, and mixtures thereof:
wherein:
R 1 is selected from:
a hydrogen atom; or
a linear C 1 -C 10 alkyl group or a branched C 3 -C 10 alkyl group, each of which is optionally substituted with one or more groups independently selected from —OR 3 and —SR 3 ;
R 2 is selected from:
a hydrogen atom;
a linear C 1 -C 12 alkyl group, a branched C 3 -C 12 alkyl group, or a C 3 -C 8 cycloalkyl group, each of which is optionally substituted with one or more groups independently selected from —OR 3 , —SR 3 , —C(O)OR 3 , and a C 5 -C 12 aryl group optionally substituted with one or more groups independently selected from OH and C 1 -C 8 alkoxy; or
a C 5 -C 12 aryl group optionally substituted with one or more groups independently selected from OH and C 1 -C 8 alkoxy;
R 3 is selected from:
a hydrogen atom; or
a linear C 1 -C 10 alkyl group or a branched C 3 -C 10 alkyl group;
ii) from about 0.2 to about 4.8 wt. % of one or more UV boosters selected from the group consisting of ethylhexyl methoxycrylene, diethyl syringylidenemalonate, and mixtures thereof, and
iii) 0 wt. % UV filters;
wherein the weight percentages are based on the total weight of the cosmetic composition; and wherein the association of the one or more UV boosters improves the photostability of the at least one thiopyridinone compound.
14 . The composition of claim 1 wherein one or more compounds of formula (I) is compound 20:
20
N-[(2-thioxo-1,2- dihydropyridin-3- yl)carbonyl]glycine