UV/visible light absorbers for ophthalmic lens materials

1. A benzotriazole compound of the formula

wherein

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

R 2 ═C 1 -C 4 alkoxy; and

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

2. A benzotriazole compound of claim 1 wherein

R 1 ═H or CH 3 ;

R 2 ═C 1 -C 4 alkoxy; and

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

3. A benzotriazole compound of claim 2 wherein the compound is selected from the group consisting of:

2-hydroxy-5-methoxy-3-(5-(trifluoromethyl)-2H-benzo[d][1,2,3]triazol-2-yl)benzyl methacrylate;

3-(5-fluoro-2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methoxybenzyl methacrylate;

3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methoxybenzyl methacrylate;

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

2-hydroxy-5-methoxy-3-(5-methoxy-2H-benzo[d][1,2,3]triazol-2-yl)benzyl methacrylate; and

2-hydroxy-5-methoxy-3-(5-methyl-2H-benzo[d][1,2,3]triazol-2-yl)benzyl methacrylate.

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

5. A benzotriazole compound of claim 3 wherein the compound is

3-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methoxybenzyl methacrylate.

6. An ophthalmic device material comprising a benzotriazole compound of claim 1 and a device-forming monomer selected from the group consisting of acrylic monomers and silicone-containing monomers.

7. The ophthalmic device material of claim 6 wherein the ophthalmic device material comprises from 0.1 to 3% w/w of a benzotriazole compound of claim 1 .

8. The ophthalmic device material of claim 7 wherein the ophthalmic device material comprises from 0.2 to 2.5% w/w of a benzotriazole compound of claim 1 .

9. The ophthalmic device material of claim 8 wherein the ophthalmic device material comprises from 0.3 to 2% w/w of a benzotriazole compound of claim 1 .

10. The ophthalmic device material of claim 6 wherein the ophthalmic device material 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 ) m or [O(CH 2 ) 2 ] z ;

C is (CH 2 ) w ;

m is 2-6;

z is 1-10;

Y is nothing, 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 wherein 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.

11. The ophthalmic device material of claim 10 wherein in formula [IV]:

A is H or CH 3 ;

B is (CH 2 ) m ;

m is 2-5;

Y is nothing or O;

w is 0-1; and

D is H.

12. The ophthalmic device material of claim 11 wherein the ophthalmic device material 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.

13. The ophthalmic device material of claim 6 wherein the ophthalmic device material comprises a cross-linking agent.

14. The ophthalmic device material of claim 6 wherein the ophthalmic device material comprises a reactive blue-light absorbing compound.

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

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

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

18. An ophthalmic device comprising the ophthalmic device material of claim 6 .

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