POLYVINYL ULTRAVIOLET LIGHT ABSORBERS FOR PERSONAL CARE
First Claim
Patent Images
1. A UV absorbing polymer, comprising at least one residue of a chromophoric monomer structure depicted by Ia or Ib below or a combination thereof:
- wherein X is hydrogen or one or two groups selected from the group consisting of hydroxy, C1-C6-alkyl, halogen, and —
OR′
;
X1 and X2 are independently selected from the group consisting of cyano, C1-C6-alkoxycarbonyl, C1-C6-alkylsulfonyl, arylsulfonyl, carbamoyl, C1-C6-alkanoyl, aroyl, aryl, heteroaryl, and —
COY;
R and R′
are independently selected from the group consisting of hydrogen, C1-C12-alkyl, substituted C1-C12-alkyl, aryl, C3-C8-cycloalkyl, C3-C8-alkenyl, —
(CHR1CHR2O—
)n—
R3, and -L-Q;
wherein R1 and R2 are independently selected from the group consisting of hydrogen and C1-C6-alkyl;
R3 is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-alkanoyl, aroyl, and aryl;
L is a divalent organic radical selected from the group consisting of C1-C6-alkylene-O—
, C1-C6-alkylene-N(R1)—
, arylene-C1-C6-alkylene-O—
, arylene-C1-C6-alkylene-(NR1)—
, arylene-(OCHR1CHR2O)n—
, C1-C6-alkylene-Y1—
(CHR1CHR2O—
)n—
, and —
(CHR1CHR2O—
)n—
;
n is 1-1000; and
Y1 is selected from the group consisting of —
O—
, —
S—
, —
SO2—
, —
N(SO2R4)—
, and —
N(COR4)—
;
Y is independently selected from the group consisting of —
O-L-Q, —
N(R4)-L-Q, —
N-(L-Q)2, and —
R4;
wherein R4 is selected from the group consisting of C1-C12-alkyl, substituted C1-C12-alkyl, C3-C8-cycloalkyl, C3-C8-alkenyl, and aryl; and
Q is a group that comprises an ethylenically unsaturated polymerizable group;
with the proviso that the monomer molecules each comprise at least one Q group.
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Abstract
UV-absorbing polymers and copolymers suitable for Composition into sunscreens for the protection of human skin. The UV-absorbing chromophoric monomers chosen are simple and easily synthesized. With the correct choice of chromophoric monomer or mixture of monomers, protection against UV-A radiation or against both UV-A and UV-B radiation can be achieved. With the correct choice of comonomer, copolymers produced as aqueous latex emulsions or as Polyethylene Glycol solutions can also be achieved.
69 Citations
24 Claims
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1. A UV absorbing polymer, comprising at least one residue of a chromophoric monomer structure depicted by Ia or Ib below or a combination thereof:
-
wherein X is hydrogen or one or two groups selected from the group consisting of hydroxy, C1-C6-alkyl, halogen, and —
OR′
;X1 and X2 are independently selected from the group consisting of cyano, C1-C6-alkoxycarbonyl, C1-C6-alkylsulfonyl, arylsulfonyl, carbamoyl, C1-C6-alkanoyl, aroyl, aryl, heteroaryl, and —
COY;R and R′
are independently selected from the group consisting of hydrogen, C1-C12-alkyl, substituted C1-C12-alkyl, aryl, C3-C8-cycloalkyl, C3-C8-alkenyl, —
(CHR1CHR2O—
)n—
R3, and -L-Q;wherein R1 and R2 are independently selected from the group consisting of hydrogen and C1-C6-alkyl; R3 is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-alkanoyl, aroyl, and aryl; L is a divalent organic radical selected from the group consisting of C1-C6-alkylene-O—
, C1-C6-alkylene-N(R1)—
, arylene-C1-C6-alkylene-O—
, arylene-C1-C6-alkylene-(NR1)—
, arylene-(OCHR1CHR2O)n—
, C1-C6-alkylene-Y1—
(CHR1CHR2O—
)n—
, and —
(CHR1CHR2O—
)n—
;n is 1-1000; and Y1 is selected from the group consisting of —
O—
, —
S—
, —
SO2—
, —
N(SO2R4)—
, and —
N(COR4)—
;Y is independently selected from the group consisting of —
O-L-Q, —
N(R4)-L-Q, —
N-(L-Q)2, and —
R4;wherein R4 is selected from the group consisting of C1-C12-alkyl, substituted C1-C12-alkyl, C3-C8-cycloalkyl, C3-C8-alkenyl, and aryl; and Q is a group that comprises an ethylenically unsaturated polymerizable group; with the proviso that the monomer molecules each comprise at least one Q group. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 23, 24)
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3. The polymer according to claim 1, wherein Q is one of a-i:
-
wherein; R5 is hydrogen or C1-C6-alkyl; R6 is selected from the group consisting of hydrogen;
C1-C6 alkyl;
phenyl;phenyl substituted with one or more groups selected from C1-C6-alkyl, C1-C6-alkoxy, —
N(C1-C6-alkyl)2, nitro, cyano, C1-C6-alkoxycarbonyl, C1-C6-alkanoyloxy, and halogen;
1- or 2-naphthyl;
1- or 2-naphthyl substituted with C1-C6-alkyl or C1-C6-alkoxy;
2- or 3-thienyl;
2- or 3-thienyl substituted with C1-C6-alkyl or halogen;
2- or 3-furyl;
or 2- or 3-furyl substituted with C1-C6-alkyl;R7 and R8 are independently selected from hydrogen, C1-C6-alkyl, or aryl;
or R7 and R8 are combined to form a
CH2
3-5 radical;R9 is hydrogen, C1-C6-alkyl, C1-C8-alkenyl, C3-C8-cycloalkyl, or aryl; and R10 is hydrogen, C1-C6-alkyl, or aryl.
-
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4. The polymer according to claim 3, wherein Q is
wherein R5 is hydrogen or methyl and R7 and R8 are methyl. -
5. The polymer according to claim 3, wherein Q is
—- C(O)C(R5)═
CHR6wherein R5 is hydrogen or methyl; and
R6 is hydrogen.
- C(O)C(R5)═
-
6. The polymer according to claim 1, further comprising at least one other ethylenically unsaturated copolymerized monomer.
-
7. The polymer according to claim 6, wherein the other ethylenically unsaturated copolymerized monomer is selected from n-butyl acrylate, methyl methacrylate, ethyl methacrylate, or methacrylic acid.
-
8. The polymer according to claim 2, wherein Q is one of a-i:
-
wherein; R5 is hydrogen or C1-C6-alkyl; R6 is selected from the group consisting of hydrogen;
C1-C6 alkyl;
phenyl;
phenyl substituted with one or more groups selected from C1-C6-alkyl, C1-C6-alkoxy, —
N(C1-C6-alkyl)2, nitro, cyano, C1-C6-alkoxycarbonyl, C1-C6-alkanoyloxy, and halogen;
1- or 2-naphthyl;
1- or 2-naphthyl substituted with C1-C6-alkyl or C1-C6-alkoxy;
2- or 3-thienyl;
2- or 3-thienyl substituted with C1-C6-alkyl or halogen;
2- or 3-furyl;
or 2- or 3-furyl substituted with C1-C6-alkyl;R7 and R8 are independently selected from hydrogen, C1-C6-alkyl, or aryl;
or R7 and R8 are combined to form a
CH2
3-5 radical;R9 is hydrogen, C1-C6-alkyl, C1-C8-alkenyl, C3-C8-cycloalkyl, or aryl; and R10 is hydrogen, C1-C6-alkyl, or aryl.
-
-
9. The polymer according to claim 8, wherein Q is
wherein R5 is hydrogen or methyl and R7 and R8 are methyl. -
10. The polymer according to claim 8, wherein Q is
—- C(O)C(R5)═
CHR6wherein R5 is hydrogen or methyl; and
R6 is hydrogen.
- C(O)C(R5)═
-
11. The polymer according to claim 2, further comprising at least one other ethylenically unsaturated copolymerized monomer.
-
12. The polymer according to claim 11, wherein the other ethylenically unsaturated copolymerized monomer is selected from n-butyl acrylate, methyl methacrylate, ethyl methacrylate, or methacrylic acid.
-
13. A polymeric UV absorbing composition, comprising the polymer according to claim 2, and a cosmetically acceptable carrier, wherein
the polymer comprises residues of monomer Ia and residues of at least one of Ib Ic, and Id, and said residues are present in a ratio of Ia/In by weight of about 99/1 to about 60/40, where In is Ib, Ic, Id, or any combination thereof. -
14. The composition according to claim 13, wherein said residues are present in a ratio of Ia/In by weight of about 99/5 to about 85/15, where In is Ib, Ic, and Id or any combination thereof.
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15. A polymeric UV absorbing composition, comprising the polymer according to claim 1 and a cosmetically acceptable carrier.
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16. The composition according to claim 15, wherein said composition contains a latex emulsion polymer.
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17. The composition according to claim 16, wherein said polymeric emulsion includes a latex dispersion of the UV absorbing polymer.
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18. A polymeric UV absorbing composition, comprising the polymer according to claim 2 and a cosmetically acceptable carrier.
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19. The composition according to claim 18, wherein said composition contains a latex emulsion polymer.
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20. The composition according to claim 19, wherein said polymeric emulsion includes a latex dispersion of the UV absorbing polymer.
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23. A composition, comprising a latex emulsion and the polymer according to claim 1.
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24. A composition, comprising a latex emulsion and the polymer according to claim 2.
-
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21. A chromophoric monomer comprising a structure depicted by Formula Ia.
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22. A chromophoric monomer comprising a structure depicted by Formula Ib
Specification