Merocyanine derivatives for cosmetic use
Described are merocyanine derivatives of formula wherein R 2 is hydrogen; C 1 -C 22 alkyl; cyclo-C 3 -C 8 alkyl; unsubstituted or C 1 -C 6 alkyl- or C 1 -C 6 alkoxy-substituted C 6 -C 20 aryl; a cyano group; or R 1 and R 2 together with the nitrogen atom linking them form a —(CH 2 ) m — ring which is optionally interrupted by —O— or by —NR 7 —; R 4 is a cyano group; or -Q 1 -R 5 ; Q 1 is —COO—; —CONH—; —CO—; —SO 2 —; or —CONR 6 —; R 5 is C 1 -C 22 alkyl; cyclo-C 3 -C 8 alkyl; or unsubstituted or C 1 -C 6 alkyl-substituted C 6 -C 20 aryl; R 6 is hydrogen; C 1 -C 22 alkyl; cyclo-C 3 -C 8 alkyl; unsubstituted or C 1 -C 6 alkyl- or C 1 -C 6 alkoxy-substituted C 6 -C 20 aryl; R 7 is hydrogen; C 1 -C 22 alkyl; cyclo-C 3 -C 8 alkyl; unsubstituted or C 1 -C 6 alkyl- or C 1 -C 6 alkoxy-substituted C 6 -C 20 aryl; the cyclohexene radical C is not substituted or substituted by one or more C 1 -C 5 alkyl; m is from 3 to 7; n is from 2 to 4; and o is from 2 to 4. Said merocyanine derivatives are useful in protecting human and animal hair and skin from UV radiation and to cosmetic compositions comprising said derivatives.
1. Compounds of formula
wherein
R 2 is hydrogen; C 1 -C 22 alkyl; cyclo-C 3 -C 8 alkyl; unsubstituted or C 1 -C 6 alkyl- or C 1 -C 6 alkoxy-substituted C 6 -C 20 aryl; or R 1 and R 2 together with the nitrogen atom linking them form a —(CH 2 ) m — ring which is optionally interrupted by —O— or —NR 3 —;
R 3 is hydrogen; C 1 -C 22 alkyl; cyclo-C 3 -C 8 alkyl; or unsubstituted or C 1 -C 6 alkyl-substituted C 6 -C 20 aryl;
m is from 3 to 7;
n is from 2 to 4;
the cyclohexene radical C is unsubstituted or substituted by one or more C 1 -C 5 alkyl;
when n=2, in formula (4)
R 1 and R 2 simultaneously form an alkylene, cycloalkylene or phenylene radical;
when n=3, in formula (4)
R 1 is a trivalent alkyl group, which is optionally interrupted by one or more —O— or —NR 3 -groups;
when n=4, in formula (4)
R 1 is a tetravalent alkyl group which is optionally interrupted by one or more —O— or —NR 3 -groups
R′ 2 is hydrogen; C 1 -C 22 alkyl; cyclo-C 3 -C 8 alkyl; unsubstituted or C 1 -C 6 alkyl- or C 1 -C 6 alkoxy-substituted C 6 -C 20 aryl; a cyano group; or R′ 1 and R′ 2 together with the nitrogen atom linking them form a —(CH 2 ) m — ring which is optionally interrupted by —O— or by —NR′ 7 —;
R′ 4 is -Q′ 1 -R′ 5 ;
Q′ 1 is —COO—; —CONH—; —CO—; —SO 2 —; or —CONR′ 6 —;
R′ 5 is C 1 -C 22 alkyl; cyclo-C 3 -C 8 alkyl; or unsubstituted or C 1 -C 6 alkyl-substituted C 6 -C 20 aryl;
R′ 6 is hydrogen; C 1 -C 22 alkyl; cyclo-C 3 -C 8 alkyl; unsubstituted or C 1 -C 6 alkyl- or C 1 -C 6 alkoxy-substituted C 6 -C 20 aryl;
R′ 7 is hydrogen; C 1 -C 22 alkyl; cyclo-C 3 -C 8 alkyl; unsubstituted or C 1 -C 6 alkyl- or C 1 -C 6 alkoxy-substituted C 6 -C 20 aryl;
o is from 2 to 4;
if n=2, in formula (1′a)
R′ 1 is an alkylene, cycloalkylene or phenylene-radical; or R′ 1 and R′ 2 simultaneously form an alkylene, cycloalkylene or phenylene radical; and
R′ 3 is a cyano group or -Q′ 1 -R′ 5 ; or R′ 3 and R′ 4 together form a 5- to 7-membered, monocyclic carbocyclic ring;
If o=2, in formula (1′b)
R′ 3 is an alkylene, cycloalkylene or phenylene radical; and
R′ 1 is hydrogen; a cyano group; C 1 -C 22 alkyl; cyclo-C 3 -C 8 alkyl; unsubstituted or C 1 -C 6 alkyl- or C 1 -C 6 alkoxy-substituted C 6 -C 20 aryl; or R 1 and R 2 together with the nitrogen atom linking them form a —(CH 2 ) m — ring which is optionally interrupted by —O— or by —NR′ 7 —;
if n=3, in formula (1′a)
R′ 1 is a trivalent alkyl group, which is optionally interrupted by one or more —O— or —NR′ 7 -groups; and
R′ 3 is a cyano group or -Q′ 1 -R′ 5 ; or R′ 3 and R′ 4 together form a 5- to 7-membered, monocyclic carbocyclic ring;
if o=3, in formula (1′b)
R′ 3 is an alkylidene, cycloalkylidene or phenylidene radical; and
R′ 1 is hydrogen; a cyano group; C 1 -C 22 alkyl; cyclo-C 3 -C 8 alkyl; unsubstituted or C 1 -C 6 alkyl- or C 1 -C 6 alkoxy-substituted C 6 -C 20 aryl; or R′ 1 and R′ 2 together with the nitrogen atom linking them form a —(CH 2 ) m — ring which is optionally interrupted by —O— or by —NR′ 7 —;
if n=4, in formula (1′a)
R′ 1 is a tetravalent alkyl group; and
R′ 3 is a cyano group or -Q′ 1 -R′ 5 ; or R′ 3 and R′ 4 together form a 5- to 7-membered, monocyclic carbocyclic ring;
if o=4, in formula (1′b)
R′ 3 is a tetravalent alkyl group; and
R′ 1 is hydrogen; a cyano group; C 1 -C 22 alkyl; cyclo-C 3 -C 8 alkyl; unsubstituted or C 1 -C 6 alkyl- or C 1 -C 6 alkoxy-substituted C 6 -C 20 aryl; or R′ 1 and R′ 2 together with the nitrogen atom linking them form a —(CH 2 ) m — ring which is optionally interrupted by —O— or by —NR′ 7 —.