Cationic alcohols and uses thereof
View Patent ↗Compositions are disclosed comprising novel fluorinated cationic alcohols in a cosmetically acceptable vehicle. The fluorinated compounds alter a surface property of the hair to provide hair conditioning, for example. In embodiments, the compounds have improved water solubility and deposition properties.
1. A compound according to the following formula:
wherein,
A′ and A″ are independently CH 2 , CHF or CF 2 ;
X′ and X″ are independently O, CF 2 , or —(CH 2 ) m —;
R 5 and R 10 are the same or different organic groups, each substituted with at least two fluorine atoms;
R 6 and R 9 are independently substituted or unsubstituted C 1-6 alkyl, and R 6 and R 9 may join to form a ring;
R 7 and R 8 are independently substituted or unsubstituted C 1-6 alkyl, and R 7 and R 8 may join to form a ring;
n is an integer from 1 to 6; and
m is an integer from 1 to 20,
including cosmetically acceptable salts thereof.
2. A compound according to claim 1 , wherein A′ and A″ are CH 2 .
3. A compound according to claim 1 , wherein X′ and X″ are CH 2 .
4. A compound according to claim 1 , wherein X′ and X″ are O.
5. A compound according to claim 1 , wherein R 5 and R 10 are the same straight or branched chain C 1-30 fluoroalkyl group.
6. A compound according to claim 5 , wherein R 5 and R 10 each have a terminal CHF 2 group.
7. A compound according to claim 1 , wherein R 6 , R 7 , R 8 , and R 9 are independently C 1-6 alkyl groups, optionally substituted with a hydroxyl group, carboxyl group, alkoxy group or acyloxy group, and wherein R 6 and R 8 are the same and R 7 and R 9 are the same.
8. A compound according to claim 1 , wherein X′ and X″ are O, A′ and A″ are CH 2 , R 5 and R 10 are the same straight or branched chain C 1-30 fluoroalkyl group having a terminal CHF 2 group, and wherein R 6 and R 8 are the same and R 7 and R 9 are the same.
9. A compound according to claim 8 , selected from the group consisting of:
including cosmetically acceptable salts thereof.
10. A compound according to claim 1 , wherein one or more of R 6 , R 7 , R 8 , and R 9 is defined by the following formula
wherein,
X is O, CF 2 , or —(CH 2 ) q —;
A is CH 2 , CFH or CF 2 ;
R 2′ and R 3′ are independently C 1-6 alkyl groups, optionally substituted with a hydroxyl group, carboxyl group, alkoxy group or acyloxy group, or any of R 2′ , and R 3′ may join to form a ring with a quaternary nitrogen;
p is an integer from 1 to 20; and
q is an integer from 1 to 20.
11. A cosmetic composition for treating hair or skin, comprising a cosmetically acceptable excipient, and a compound of the following formula:
wherein,
A′ and A″ are independently CH 2 , CHF or CF 2 ;
X′ and X″ are independently O, CF 2 , or —(CH 2 ) m —;
R 5 and R 10 are the same or different organic groups, each substituted with at least two fluorine atoms;
R 6 and R 9 are independently substituted or unsubstituted C 1-6 alkyl, and R 6 and R 9 may join to form a ring;
R 7 and R 8 are independently substituted or unsubstituted C 1-6 alkyl, and R 7 and R 8 may join to form a ring;
n is an integer from 1 to 6; and
m is an integer from 1 to 20
including cosmetically acceptable salts thereof.
12. A composition according to claim 11 , wherein A′ and A″ are CH 2 .
13. A composition according to claim 11 , wherein X′ and X″ are CH 2 .
14. A composition according to claim 11 , wherein X′ and X″ are O.
15. A composition according to claim 11 , wherein R 5 and R 10 are the same straight or branched chain C 1-30 fluoroalkyl group.
16. A composition according to claim 15 , wherein R 5 and R 10 each have a terminal CHF 2 group.
17. A composition according to claim 11 wherein R 6 , R 7 , R 8 , and R 9 are independently C 1-6 alkyl groups, optionally substituted with a hydroxyl group, carboxyl group, alkoxy group or acyloxy group, and wherein R 6 and R 8 are the same and R 7 and R 9 are the same.
18. A composition according to claim 11 , wherein X′ and X″ are O, A′ and A″ are CH 2 , R 5 and R 10 are the same straight or branched chain C 1-30 fluoroalkyl group having a terminal CHF 2 group, and R 6 and R 8 are the same and R 7 and R 9 are the same.
19. The composition according to claim 18 , wherein the compound has the following structure:
including cosmetically acceptable salts thereof.
20. A composition according to claim 11 , wherein one or more of R 6 , R 7 , R 8 , and R 9 is defined by the following formula:
wherein,
X is O, or —(CH 2 ) q —;
A is CH 2 , CFH or CF 2 ;
R 2′ and R 3′ are independently hydrogen; aliphatic; heteroaliphatic; acyl; aryl; or heteroaryl; any of which may be substituted or unsubstituted; or any of R 2′ , and R 3′ may join to form a ring with a quaternary nitrogen;
p is an integer from 1 to 20; and
q is an integer from 1 to 20.
21. A method of treating hair, comprising applying a composition according to claim 11 to hair.
22. A hair treatment composition comprising the reaction product of a fluorinated epoxide and a tertiary amine, including cosmetically acceptable salts of said reaction product, in a cosmetically acceptable excipient, said reaction product comprising a quaternary ammonium moiety, a hydroxyl group, and containing at least two fluorine atoms.
23. A composition according to claim 22 , wherein said fluorinated epoxide and said reaction product are not perfluorinated.
24. A composition according to claim 23 , wherein said fluorinated epoxide and said reaction product contain a terminal CHF 2 group.
25. A compound according the following formula:
and cosmetically acceptable salts thereof.