Visible light absorbers for ophthalmic lens materials

1. An azo compound of the formula

wherein

X 1 , X 2 , and X 3 independently=H, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, phenoxy, or benzyloxy;

Y=H, F, Cl, Br, I, or C 1 -C 6 alkyl;

W=nothing or —O—C(═O)—NH—CH 2 —CH 2 —; and

Z=H, CH 3 , C 2 H 5 , or CH 2 OH.

2. The azo compound of claim 1 wherein

X 1 , X 2 , and X 3 independently=H, C 1 -C 4 alkyl, or C 1 -C 4 alkoxy,

Y=H, Cl or C 1 -C 4 alkyl;

W=nothing; and

Z is H or CH 3 .

3. The azo compound of claim 2 wherein the compound is selected from the group consisting of: 2-hydroxy-3-((4-methoxyphenyl)diazenyl)-5-methylbenzyl methacrylate; 2-hydroxy-5-methyl-3-((3,4,5-trimethoxy-phenyl)diazenyl)benzyl methacrylate; and 5-chloro-2-hydroxy-3-((4-methoxyphenyl)diazenyl)benzyl methacrylate.

4. The azo compound of claim 3 wherein the compound is 2-hydroxy-3-((4-methoxyphenyl)diazenyl)-5-methylbenzyl methacrylate.

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

6. The ophthalmic device material of claim 5 wherein the ophthalmic device material comprises from 0.005 to 0.2% (w/w) of the azo compound.

7. The ophthalmic device material of claim 6 wherein the ophthalmic device material comprises from 0.01 to 0.08% (w/w) of the azo compound.

8. The ophthalmic device material of claim 7 wherein the ophthalmic device material comprises from 0.01 to 0.05% (w/w) of the azo compound.

9. The ophthalmic device material of claim 5 wherein the ophthalmic device material comprises a device-forming monomer of formula [II]:

where in formula [II]:

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 (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.

10. The ophthalmic device material of claim 9 wherein in formula [II]:

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.

11. The ophthalmic device material of claim 10 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.

12. The ophthalmic device material of claim 5 wherein the ophthalmic device material comprises a cross-linking agent.

13. The ophthalmic device material of claim 5 wherein the ophthalmic device material comprises a reactive UV absorbing compound.

14. An intraocular lens comprising an azo compound of claim 1 .

15. An intraocular lens comprising an azo compound of claim 2 .

16. An intraocular lens comprising an azo compound of claim 3 .

17. An ophthalmic device comprising the ophthalmic device material of claim 5 .

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; and a corneal inlay or ring.