UV-absorbing and photostabilizing polymers

1. A polymer comprising a monomer having a formula (I):

wherein:

R 1 and R 2 are each independently selected from the group consisting of C 1 -C 50 alkyl, C 2 -C 50 alkenyl, alkynyl, C 3 -C 8 cycloalkyl, C 2 -C 50 polyether, C 2 -C 500 substituted polyether, C 1 -C 50 substituted alkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkynyl, C 3 -C 8 substituted cycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocycloalkyl, substituted heterocycloalkyl, halo, C(O)OR a , OC(O)R a , C(O)H, C(O)R a , C(O)NR a R b , —C(O)SR a , OR a , —SR a , NR a R b , —CN, and

X is O, S, or NR c ;

W is —C(O)OR z , —C(O)R z —, —C(O)NR d R z —, —C(O)SR z —, —SR z —, —NR e R z —, or a bond;

n is 3 to 30;

k and m are each independently selected from 0 to 5;

R a , R b , R c , R d , and R e are each independently selected from the group consisting of: hydrogen, C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkynyl, C 3 -C 8 cycloalkyl, C 1 -C 50 substituted alkyl, C 2 -C 50 substituted alkenyl, C 1 -C 50 substituted alkynyl, C 3 -C 8 substituted cycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocycloalkyl, and substituted heterocycloalkyl; and

R z alkylene, C 1 -C 50 alkenylene, C 7 -C 50 alkynylene, cycloalkyl, C 1 -C 50 substituted alkylene, C 2 -C 50 substituted alkenylene, C 2 -C 50 substituted alkynylene, C 3 -C 8 substituted cycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocycloalkyl, or substituted heterocycloalkyl;

with the proviso that when W is —C(O)OR z —, n is 8 to 30.

2. A UV-absorbing composition comprising the polymer of claim a dibenzoylmethane derivative, and a cinnamate ester.

3. A method of preparing a UV-absorbing film comprising: providing a solution comprising the polymer of claim 1 and an organic solvent, applying the solution to a surface, and removing the solvent.

4. The method of claim 3 , further comprising a monomer selected from the group consisting of a monomer having a formula (II), a monomer having a formula (III), a monomer having a formula (IIIA), a monomer having a formula (IV), a monomer having a formula (V), a monomer having a formula (VI), and combinations thereof:

wherein:

R 3 and R 5 are each independently selected from the group consisting of: hydrogen, fluoride, chloride, iodide, C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkynyl, C 3 -C 8 cycloalkyl, C 1 -C 50 substituted alkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkynyl, C 3 -C 8 substituted cycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocycloalkyl, substituted heterocycloalkyl, and halo; and

R 4 and R 6 are each independently selected from the group consisting of hydrogen, C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkynyl, C 3 -C 8 cycloalkyl, C 2 -C 50 polyether, C 2 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkynyl, C 3 -C 8 substituted cycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocycloalkyl, substituted heterocycloalkyl, halo, —C(O)OR x , —OC(O)R x , —C(O)H, —C(O)R x , —C(O)NR x R y , —C(O)SR x , —OR x , —SR x , —NR x R y , —CN, and —NO 2 ; or

R 4 and R 6 taken together with the atoms to which they are bonded form a 5 to 7 membered heterocyclic ring or a substituted 5 to 7 membered heterocyclic ring;

R x and R y are each independently selected from the group consisting of: hydrogen, C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkynyl, C 3 -C 8 cycloalkyl, C 1 -C 50 substituted alkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkynyl, C 3 -C 8 substituted cycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocycloalkyl, and substituted heterocycloalkyl;

X 1 , X 2 , X 3 , X 4 , and X 5 are each independently selected from the group consisting O, S, and NR f ; and

R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , and R f are each independently selected from the group consisting of: hydrogen, C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkynyl, C 3 -C 8 cycloalkyl, C 1 -C 50 substituted alkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkynyl, C 3 -C 8 substituted cycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocycloalkyl, and substituted heterocycloalkyl, or R 10 and R f taken together with the atoms to which they are bonded form a 5 or 6 membered ring.

5. The method of claim 3 , further comprising a monomer selected from the group consisting of maleic anhydride monomers, methyl methacrylate monomers, vinyl acetate monomers, C 3 -C 38 alpha-olefin monomers, N-vinyl pyrrolidone monomers, styrene monomers, and combinations thereof.

6. The method of claim 3 , wherein n is 8 to 13.

7. The method of claim 3 , wherein X is 0.

8. The method of claim 3 , wherein k and m are both 0.

9. The method of claim 3 , wherein k is 1, m is 0, and R 1 is —OR a ; or k is 0, m is 1, and R 2 is —OR a .

10. The method of claim 9 , wherein R a is C 1 -C 3 alkyl.

11. The method of claim 9 , wherein R 1 is —OCH 3 or R 2 is —OCH 3 .

12. The method of claim 3 , wherein the monomer having a formula (I) is selected from the group consisting of a monomer having a formula (VIII) and a monomer having a formula (IX):

wherein:

k is 0 or 1; and

R 1 is —OR a .

13. The method of claim 12 , wherein R a is C 1 -C 3 alkyl.

14. The method of claim 3 , wherein the weight-average molecular weight of said polymer is in the range of about 1,000 to about 1,000,000.

15. A method of waterproofing a surface comprising: providing a solution comprising the polymer of claim 1 and an organic solvent, applying the solution to a surface, and removing the solvent.

16. The method of claim 15 , further comprising a monomer selected from the group consisting of a monomer having a formula (II), a monomer having a formula (III), a monomer having a formula (IIIA), a monomer having a formula (IV), a monomer having a formula (V), a monomer having a formula (VI), and combinations thereof:

wherein:

R 3 and R 5 are each independently selected from the group consisting of: hydrogen, fluoride, chloride, iodide, C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkynyl, C 3 -C 8 cycloalkyl, C 1 -C 50 substituted alkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkynyl, C 3 -C 8 substituted cycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocycloalkyl, substituted heterocycloalkyl, and halo; and

R 4 and R 6 are each independently selected from the group consisting of hydrogen, C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkynyl, C 3 -C 8 cycloalkyl, C 2 -C 50 polyether, C 2 -C 50 substituted polyether, C 1 -C 50 substituted alkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkynyl, C 3 -C 8 substituted cycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocycloalkyl, substituted heterocycloalkyl, halo, —C(O)OR x , —OC(O)R x , —C(O)H, —C(O)R x , —C(O)NR x R y , —C(O)SR x , —OR x , —SR x , —NR x R y , —CN, and —NO 2 ; or

R 4 and R 6 taken together with the atoms to which they are bonded form a 5 to 7 membered heterocyclic ring or a substituted 5 to 7 membered heterocyclic ring;

R x and R y are each independently selected from the group consisting of: hydrogen, C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkynyl, C 3 -C 8 cycloalkyl, C 1 -C 50 substituted alkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkynyl, C 3 -C 8 substituted cycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocycloalkyl, and substituted heterocycloalkyl;

X 1 , X 2 , X 3 , X 4 , and X 5 are each independently selected from the group consisting O, S, and NR f ; and

R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , and R f are each independently selected from the group consisting of: hydrogen, C 1 -C 50 alkyl, C 2 -C 50 alkenyl, C 2 -C 50 alkynyl, C 3 -C 8 cycloalkyl, C 1 -C 50 substituted alkyl, C 2 -C 50 substituted alkenyl, C 2 -C 50 substituted alkynyl, C 3 -C 8 substituted cycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocycloalkyl, and substituted heterocycloalkyl, or R 10 and R f taken together with the atoms to which they are bonded form a 5 or 6 membered ring.

17. The method of claim 15 , further comprising a monomer selected from the group consisting of maleic anhydride monomers, methyl methacrylate monomers, vinyl acetate monomers, C 3 -C 38 alpha-olefin monomers, N-vinyl pyrrolidone monomers, styrene monomers, and combinations thereof.

18. The method of claim 15 , wherein n is 8 to 13.

19. The method of claim 15 , wherein X is O.

20. The method of claim 15 , wherein k and m are both 0.

21. The method of claim 15 , wherein k is 1, m is 0, and R 1 is —OR a ; or k is 0, m is 1, and R 2 is —OR a .

22. The method of claim 21 , wherein R a is C 1 -C 3 alkyl.

23. The method of claim 21 , wherein R 1 is —OCH 3 or R 2 is —OCH 3 .

24. The method of claim 15 , wherein the monomer having a formula (I) is selected from the group consisting of a monomer having a formula (VIII) and a monomer having a formula (IX):

wherein:

k is 0or 1; and

R 1 is —OR a .

25. The method of claim 24 , wherein R a is C 1 -C 3 alkyl.

26. The method of claim 15 , wherein the weight-average molecular weight of said polymer is in the range of about 1,000 to about 1,000,000.