Triazine derivatives as UV absorbers
The present invention relates to new compounds of formula (I), wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 independently from each other are hydrogen; C 1 -C 18 alkyl; C 2 -C 18 alkenyl; C 5 -C 7 , cycloalkyl; C 1 -C 6 alkylene-C 5 -C 7 , cycloalkyl; R 9 is hydrogen; C 1 -C 18 alkyl; C 2 -C 18 alkenyl; C 5 -C 7 cycloalkyl; C 1 -C 6 alkylene-C 5 -C 7 cycloalkyl; C 6 -C 10 aryl; A is —S—; —O— or —NR 10 —, wherein R 10 has the same meanings as R 9 ; X is COOR 11 ; CONR 12 R 13 ; SO 3 , R 14 ; or SO 2 NR 15 R 16 , wherein R 11 , R 12 , R 13 , R 14 , R 15 , and R 16 , have independently from each other the same meanings as R 9 ; to their preparation and to their use as UV absorbers in cosmetic and pharmaceutical formulations.
1. A UV absorber represented by compound of formula (1)
wherein
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 independently from each other are hydrogen; C 1 -C 18 alkyl; C 2 -C 18 alkenyl; C 5 -C 7 cycloalkyl or C 1 -C 6 alkylene-C 5 -C 7 cycloalkyl;
R 9 is C 1 -C 18 alkyl; C 2 -C 18 alkenyl; C 5 -C 7 cycloalkyl; C 1 -C 6 alkylene-C 5 -C 7 cycloalkyl or C 6 -C 10 aryl;
A is —S—; or —NR 10 —, wherein R 10 is hydrogen, C 1 -C 18 alkyl; C 2 -C 18 alkenyl; C 5 -C 7 cycloalkyl; C 1 -C 6 alkylene-C 5 -C 7 cycloalkyl or C 6 -C 10 aryl;
and
X is COOR 11 ; CONR 12 R 13 ; SO 3 R 14 or SO 2 NR 15 R 16 , wherein R 11 , R 12 , R 13 , R 14 , R 15 and R 16 are independently from each other hydrogen, C 1 -C 18 alkyl; C 2 -C 18 alkenyl; C 5 -C 7 cycloalkyl; C 1 -C 6 alkylene-C 5 -C 7 cycloalkyl or C 6 -C 10 aryl.
2. A compound according to claim 1 , wherein
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 independently from each other are hydrogen; C 1 -C 10 alkyl; C 2 -C 10 alkenyl; C 5 -C 7 cycloalkyl or C 1 -C 4 alkylene-C 5 -C 7 cycloalkyl;
R 5 is hydrogen; C 1 -C 10 alkyl; C 2 -C 10 alkenyl; C 5 -C 7 cycloalkyl; C 1 -C 4 alkylene-C 5 -C 7 cycloalkyl; naphthyl or phenyl;
A is —S—; or —NR 10 —, wherein R 10 is hydrogen, C 1 -C 18 alkyl; C 2 -C 18 alkenyl; C 5 -C 7 cycloalkyl; C 1 -C 6 alkylene-C 5 -C 7 cycloalkyl or C 6 -C 10 aryl;
and
X is COOR 11 ; CONR 12 R 13 ; SO 3 R 14 or SO 2 NR 15 R 16 , wherein R 11 , R 12 , R 13 , R 14 , R 15 and R 16 have independently from each other are hydrogen, C 1 -C 18 alkyl; C 2 -C 18 alkenyl; C 5 -C 7 cycloalkyl; C 1 -C 6 alkylene-C 5 -C 7 cycloalkyl or C 6 -C 10 aryl.
3. A compound according to claim 1 , wherein
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are hydrogen.
4. A compound according to claim 1 , wherein
R 11 , R 12 , R 13 , R 14 , R 15 and R 16 are hydrogen or C 1 -C 12 alkyl.
5. A compound according to claim 1 , wherein
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , are hydrogen; and
R 10 , R 11 , R 12 , R 13 , R 14 , R 15 and R 16 are hydrogen or C 1 -C 12 alkyl.
6. A compound according to claim 1 of formula (2)
7. A compound of formula (3)
R 9 is C 1 -C 5 alkyl; and
R 17 is hydrogen; C 1 -C 12 alkyl or —NH 2 .
8. A process for the preparation of a compound of formula (1) according to claim 1 , which process comprises reacting one mol of at least one compound of formula (4)
wherein
Y is halogen;
with at least two mols of at least one compound of formula (5)
where
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 independently from each other are hydrogen; C 1 -C 18 alkyl; C 2 -C 18 alkenyl; C 5 -C 7 cycloalkyl or C 1 -C 6 alkylene-C 5 -C 7 cycloalkyl;
R 9 is C 1 -C 18 alkyl; C 2 -C 18 alkenyl; C 5 -C 7 cycloalkyl; C 1 -C 6 alkylene-C 5 -C 7 cycloalkyl or C 6 -C 10 aryl;
A is —S—; or —NR 10 —, wherein R 10 is hydrogen, C 1 -C 18 alkyl; C 2 -C 18 alkenyl; C 5 -C 7 cycloalkyl; C 1 -C 6 alkylene-C 5 -C 7 cycloalkyl or C 6 -C 10 aryl; and
X is COOR 11 ; CONR 12 R 13 ; SO 3 R 14 or SO 2 NR 15 R 16 , wherein R 11 , R 12 , R 13 , R 14 , R 15 and R 16 are independently hydrogen, C 1 -C 18 alkyl; C 2 -C 18 alkenyl; C 5 -C 7 cycloalkyl; C 1 -C 6 alkylene-C 5 -C 7 cycloalkyl or C 6 -C 10 aryl.
9. A cosmetic preparation comprising at least one or more compounds of formula (1) according to claim 1 together with cosmetically tolerable carriers or adjuvants.
10. A preparation according to claim 9 that further comprises in addition to the UV absorber of formula (1) further UV protective agents.
11. A preparation according to claim 9 wherein the compound of formula (1) is in micronised form having an average particle size from 0.02 to 2 micrometers.