UV/visible light absorbers for ophthalmic lens materials

1. A benzotriazole compound of the formula

wherein

X═C 3 -C 4 alkenyl, C 3 -C 4 alkyl, CH 2 CH 2 CH 2 SCH 2 CH 2 or CH 2 CH 2 CH 2 SCH 2 CH 2 CH 2 ;

Y=nothing if X═C 3 -C 4 alkenyl, otherwise

Y═—O—C(═O)—C(R 1 )═CH 2 , —O—C(═O)NHCH 2 CH 2 OC(═O)—C(R 1 )═CH 2 , or —O—C(═O)NHC(CH 3 ) 2 (C 6 H 4 )C(CH 3 )═CH 2 ;

R 1 ═H, CH 3 , CH 2 CH 3 , or CH 2 OH;

R 2 ═C 1 -C 4 alkyl; and

R 3 ═H, CH 3 , CH 3 O, F, Cl, Br, I, or CF 3 .

2. The benzotriazole compound of claim 1 , wherein

X═C 3 -C 4 alkenyl, C 3 -C 4 alkyl, or CH 2 CH 2 CH 2 SCH 2 CH 2 ;

Y=nothing if X═C 3 -C 4 alkenyl, otherwise Y═—O—C(═O)—C(R 1 )═CH 2 ;

R 1 ═H or CH 3 ;

R 2 ═C 1 -C 2 alkyl; and

R 3 ═CH 3 , CH 3 O, F, Cl, or CF 3 .

3. An intraocular lens comprising a benzotriazole compound of claim 2 .

4. The benzotriazole compound of claim 2 , wherein the compound is selected from the group consisting of:

2-(3-(3-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxy-5-methoxy-phenyl)propylthio)ethyl methacrylate;

4-allyl-2-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-6-methoxyphenol;

3-(3-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxy-5-methoxyphenyl)-propyl methacrylate;

4-allyl-2-methoxy-6-(5-(trifluoromethyl)-2H-benzo[d][1,2,3]-triazol-2-yl)phenol; and

3-(4-hydroxy-3-methoxy-5-(5-(trifluoromethyl)-2H-benzo[d][1,2,3]triazol-2-yl)phenyl)propyl methacrylate.

5. The benzotriazole compound of claim 4 , wherein the compound is 2-(3-(3-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxy-5-methoxy-phenyl)propylthio)ethyl methacrylate.

6. The benzotriazole compound of claim 4 , wherein the compound is 3-(4-hydroxy-3-methoxy-5-(5-(trifluoromethyl)-2H-benzo[d][1,2,3]triazol-2-yl)phenyl)propyl methacrylate.

7. An intraocular lens comprising a benzotriazole compound of claim 4 .

8. A copolymeric ophthalmic device material formed by copolymerizing a composition comprising a benzotriazole compound of claim 1 and a device-forming monomer selected from the group consisting of acrylic monomers and silicone-containing monomers.

9. The ophthalmic device material of claim 8 , wherein the composition comprises from 0.1 to 5% w/w of the benzotriazole compound.

10. The ophthalmic device material of claim 9 , wherein the composition comprises from 0.5 to 4% w/w of the benzotriazole compound.

11. The ophthalmic device material of claim 10 , wherein the composition comprises from 1 to 3% w/w of the benzotriazole compound.

12. The ophthalmic device material of claim 8 , wherein the composition comprises a device-forming monomer of formula [IV]:

where in formula [IV]:

A is H, CH 3 , CH 2 CH 3 , or CH 2 OH;

B is (CH 2 ), or [O(CH 2 ) 2 ] z ;

C is (CH 2 ) w ;

m is 2-6;

z is 1-10;

Y is a direct bond, O, S, or NR′, provided that if Y is O, S, or NR′, then B is (CH 2 ) m ;

R′ is H, CH 3 , C n ′H 2n+1 (n′=1-10), iso-OC 3 H 7 , C 6 H 5 , or CH 2 C 6 H 5 ;

w is 0-6, provided that m+w≦8; and

D is H, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 6 H 5 , CH 2 C 6 H 5 or halogen.

13. The ophthalmic device material of claim 12 , wherein in formula [IV]:

A is H or CH 3 ;

B is (CH 2 ) m ;

m is 2-5;

Y is a direct bond or O;

w is 0-1; and

D is H.

14. The ophthalmic device material of claim 13 , wherein the composition comprises a monomer selected from the group consisting of: 2-phenylethyl methacrylate; 4-phenylbutyl methacrylate; 5-phenylpentyl methacrylate; 2-benzyloxyethyl methacrylate; and 3-benzyloxypropyl methacrylate; and their corresponding acrylates.

15. The ophthalmic device material of claim 8 , wherein the composition comprises a cross-linking agent.

16. The ophthalmic device material of claim 8 , wherein the composition comprises a reactive blue-light absorbing compound.

17. An ophthalmic device comprising the ophthalmic device material of claim 8 .

18. The ophthalmic device of claim 17 , wherein the ophthalmic device is selected from the group consisting of an intraocular lens; a contact lens; a keratoprosthesis; a corneal inlay; and a corneal ring.

19. An intraocular lens comprising a benzotriazole compound of claim 1 .