Solubilizing agents for UV filters in cosmetic formulations
The present invention relates to the use of the compounds (A) corresponding to formula wherein R 1 is hydrogen; a linear or branched C 1 -C 30 aliphatic hydrocarbon residue comprising 0, 1, 2 or 3 double bonds; R 2 independently from each other are hydrogen; methyl; ethyl; —OH; —COOR 4 ; —CH 2 —OH; and —CH 2 —COOR 4 ; R 4 is hydrogen; or a linear or branched C 1 -C 30 aliphatic hydrocarbon residue comprising 0, 1, 2 or 3 double bonds; R 3 independently from each other are hydrogen; methyl; ethyl; —OH; —COOR 5 ; —CH 2 —OH; and —CH 2 —COOR 5 ; R 5 is hydrogen; or a linear or branched C 1 -C 30 aliphatic hydrocarbon residue comprising 0, 1, 2 or 3 double bonds; n is at least 0.1 on average; m1 and m2 independently from each other are 0; or 1; with the proviso, that at least one of the radicals R 1 , R 4 or R 5 represent a linear or branched C 1 -C 30 aliphatic hydrocarbon residue comprising 0, 1, 2 or 3 double bonds, as solubilizing agent for organic UV filters (B) selected from (B1) benzophenone derivatives; (B2) hydroxyphenyl triazine derivatives; and (B3) trianilino-s-triazine derivatives.
1. A solubilizing agent for an organic UV filter corresponding to formula (1)
wherein
R 1 is hydrogen; or a linear or branched C 1 -C 30 aliphatic hydrocarbon residue comprising 0, 1, 2 or 3 double bonds;
R 2 independently from each other are hydrogen; methyl; ethyl; —OH; —COOR 4 ; —CH 2 —OH; or —CH 2 —COOR 4 ;
R 4 is hydrogen; or a linear or branched C 1 -C 30 aliphatic hydrocarbon residue comprising 0, 1, 2 or 3 double bonds;
R 3 independently from each other are hydrogen; methyl; ethyl; —OH; —COOR 5 ; —CH 2 —OH; or —CH 2 —COOR 5 ;
R 5 is hydrogen; or a linear or branched C 1 -C 30 aliphatic hydrocarbon residue comprising 0, 1, 2 or 3 double bonds;
n is at least 0.1 on average;
m1 and m2 independently from each other are 0 or 1;
with the proviso, that at least one of the radicals R 1 , R 4 or R 5 represent a linear or branched C 1 -C 30 aliphatic hydrocarbon residue comprising 0, 1, 2 or 3 double bonds, wherein the organic UV filter is selected from the group consisting of
(B1) benzophenone derivatives corresponding to the formula
wherein
R 1 and R 2 independently from each other are hydrogen; C 1 -C 20 alkyl; C 3 -C 10 cycloalkyl; or C 3 -C 10 cycloalkenyl, wherein the radicals R 1 and R 2 together with the nitrogen atom, to which they are bonded may form a 5- or 6-membered ring; and
R 3 is C 1 -C 20 alkyl;
(B2) hydroxyphenyl triazine derivatives corresponding to the formula
wherein
R 1 and R 2 independently from each other are C 1 -C 18 alkyl; and
R 3 is C 1 -C 10 alkoxy;
(B3) trianilino-s-triazine derivatives corresponding to the formula
wherein
R 1 , R 2 and R 3 independently from each other are C 1 -C 20 alkyl, C 6 -C 10 aryl or C 6 -C 10 eteroaryl;
X is O; or NR 4 ; and
R 4 is hydrogen; or C1-C20alkyl, aryl or heteroaryl;
and mixtures thereof.
2. The solubilizing agent according to claim 1 , wherein;
m1 and m2 have the same meaning.
3. The solubilizing agent according to claim 1 , wherein the compounds of formula (1) are derived from lactic acid, glycolic acid, malic acid, tartaric acid or mixtures thereof.
4. The solubilizing agent according to claim 1 , wherein the compound of formula (1) corresponds to formula (2)
wherein
R 1 is hydrogen; or a linear or branched C 1 -C 30 aliphatic hydrocarbon residue comprising 0, 1, 2 or 3 double bonds; and
n is at least 0.1 on average.
5. The solubilizing agent according to claim 1 , wherein
n is a value from 0.1 to 100.
6. The solubilizing agent according to claim 1 , wherein
at least one of the radicals R 1 , R 4 and R 5 in formula (1) is methyl; ethyl; n-propyl; isopropyl; n-butyl; isobutyl; sec.-butyl; tert.-butyl; n-pentyl; isoamyl; n-hexyl; 2-ethylhexyl; n-heptyl; n-octyl; n-nonyl, n-decyl, 2-propylheptyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl; n-hexadecyl; n-heptadecyl; n-octadecyl; n-nonadecyl; arachinyl; behenyl; lignocerinyl; melissinyl; isotridecyl; isostearyl; oleyl; linoleyl; linolenyl or a combination of at least two of these radicals.
7. The solubilizing agent according to claim 1 , wherein
at least one of the radicals R 1 , R 4 and R 5 is derived from a mixture of linear saturated C 12 -C 14 -alcohols.
8. The solubilizing agent according to claim 1 , wherein the organic UV filters (B) are used in admixtures of at least two different UV filters selected from (B1), (B2) and (B3).
9. The solubilizing agent according to claim 1 , wherein the organic UV filter (B) is a benzophenone derivative (B1).
10. The solubilizing agent according to claim 1 , wherein the benzophenone derivatives (B1) correspond to the formula
11. The solubilizing agent according to claim 1 , wherein the organic UV filter (b) is a hydroxyphenyl triazine derivative (B2).
12. The solubilizing agent according to claim 1 , wherein the hydroxyphenyl triazine derivatives (B2) correspond to formula
13. The solubilizing agent according to claim 1 , wherein the hydroxyphenyl triazine derivatives (B2) correspond to formula
14. The solubilizing agent according to claim 1 , wherein the organic UV filter (B) is a trianilino-s-triazine derivative (B3).
15. The solubilizing agent according to claim 1 , wherein the trianilino-s-triazine derivatives (B3) correspond to the formula
16. The solubilizing agent according to claim 1 , wherein the organic UV filter is a mixture of a benzophenone derivative corresponding to the formula
a hydroxyphenyl triazine derivative corresponding to formula
and a trianilino-s-triazine derivative corresponding to the formula
17. The solubilizing agent according to claim 1 , wherein the organic UV filter is a mixture of
a benzophenone derivative corresponding to the formula
and a hydroxyphenyl triazine derivative corresponding to formula
18. The solubilizing agent according to claim 1 , wherein the organic UV filter is a mixture of
a benzophenone derivative corresponding to the formula
and a trianilino-s-triazine derivative corresponding to the formula
19. The solubilizing agent according to claim 1 , wherein the organic UV filter is a mixture of
a hydroxyphenyl triazine derivative corresponding to formula
a trianilino-s-triazine derivative corresponding to the formula
20. The solubilizing agent according to claim 1 , wherein the solubilizing agent is a compound of formula
wherein
R 1 is hydrogen; or a linear or branched C 1 -C 30 aliphatic hydrocarbon residue comprising 0, 1, 2 or 3 double bonds; and
n is at least 0.1 on average;
and the organic UV filter is selected from the group consisting of:
a benzophenone derivative corresponding to the formula
a hydroxyphenyl triazine derivative corresponding to formula
a trianilino-s-triazine derivative corresponding to the formula
and mixtures thereof.
21. A cosmetic composition comprising
(A) a compound of formula
wherein
R 1 is hydrogen; or a linear or branched C 1 -C 30 aliphatic hydrocarbon residue comprising 0, 1, 2 or 3 double bonds;
R 2 independently from each other are hydrogen; methyl; ethyl, —OH; —COOR 4 ; —CH 2 —OH; or —CH 2 —COOR 4 ;
R 4 is hydrogen; or a linear or branched C 1 -C 30 aliphatic hydrocarbon residue comprising 0, 1, 2 or 3 double bonds;
R 3 independently from each other are hydrogen; methyl; ethyl; —OH; —COOR 5 ; —CH 2 —OH; or —CH 2 —COOR 5 ;
R 5 is hydrogen; or a linear or branched C 1 -C 30 aliphatic hydrocarbon residue comprising 0, 1, 2 or 3 double bonds;
n is at least 0.1;
m1 and m2 independently from each other are 0 or 1;
with the proviso, that at least one of the radicals R1, R4 or R5 are a linear or branched C1-C30 aliphatic hydrocarbon residue comprising 0, 1, 2 or 3 double bonds; and
(B) an organic UV filter selected from the group consisting of
(B1) benzophenone derivatives corresponding to the formula
wherein
R 1 and R 2 independently from each other are hydrogen; C 1 -C 20 alkyl; C 3 -C 10 cycloalkyl; or C 3 -C 10 cycloalkenyl, wherein the radicals R 1 and R 2 together with the nitrogen atom, to which they are bonded may form a 5- or 6-membered ring; and
R 3 is C 1 -C 20 alkyl,
(B2) hydroxyphenyl triazine derivatives corresponding to the formula
wherein
R 1 and R 2 independently from each other are C 1 -C 18 alkyl; and
R 3 is C 1 -C 10 alkoxy;
(B3) trianilino-s-triazine derivatives corresponding to the formula
wherein
R 1 , R 2 and R 3 independently from each other are C 1 -C 20 alkyl, C 6 -C 10 aryl or C 6 -C 10 eteroaryl;
X is O; or NR 4 ; and
R 4 is hydrogen; or C1-C20alkyl, aryl or heteroaryl,
and mixtures thereof.
22. The composition according to claim 21 , wherein the solubilizing agent (A) corresponds to formula
wherein
R 1 is hydrogen; or a linear or branched C 1 -C 30 aliphatic hydrocarbon residue comprising 0, 1, 2 or 3 double bonds; and
n is at least 0.1 on average.