Visible light absorbers for ophthalmic lens materials

1. An azo compound of the formula

wherein

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

R 2 =H, C 1 -C 4 alkyl, or C 1 -C 4 alkoxy;

R 3 =H, C 1 -C 4 alkyl, F, Cl, Br, CN, NO 2 , COOR 4 ; XOC(O)CH═CH 2 , XOC(O)C(CH 3 )═CH 2 , XOC(O)NHCH 2 CH 2 OC(O)C(CH 3 )═CH 2 , or XOC(O)NHC(CH 3 ) 2 C 6 H 4 C(CH 3 )═CH 2 ;

R 4 =H or C 1 -C 4 alkyl; and

X=C 1 -C 4 alkyl or C 2 -C 4 alkenyl.

2. The azo compound of claim 1 wherein

R 1 =C(O)CH═CH 2 , C(O)C(CH 3 )═CH 2 , C(O)NHCH 2 CH 2 OC(O)C(CH 3 )═CH 2 ;

R 2 =H or C 1 -C 4 alkyl;

R 3 =H, C 1 -C 4 alkyl, F, Cl, Br, CN, NO 2 , COOR 4 ; XOC(O)CH═CH 2 , XOC(O)C(CH 3 )═CH 2 , or XOC(O)NHCH 2 CH 2 OC(O)C(CH 3 )═CH 2 ;

R 4 =C 1 -C 4 alkyl; and

X=C 1 -C 4 alkyl.

3. The azo compound of claim 2 wherein

R 1 =C(O)C(CH 3 )═CH 2 or C(O)NHCH 2 CH 2 OC(O)C(CH 3 )═CH 2 ;

R 2 =H;

R 3 =H, C 1 -C 4 alkyl, F, Cl, Br, XOC(O)C(CH 3 )═CH 2 or XOC(O)NHCH 2 CH 2 OC(O)C(CH 3 )═CH 2 ; and

X=C 1 -C 4 alkyl.

4. The azo compound of claim 2 wherein the compound is selected from the group consisting of (E)-4-((2-hydroxy-5-methylphenyl)diazenyl)phenethyl methacrylate and (E)-4-hydroxy-3-((4-(2-(methacryloyloxy)ethyl)phenyl)diazenyl)phenethyl methacrylate.

5. An ophthalmic device material comprising the 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 of claim 1 .

7. The ophthalmic device material of claim 6 wherein the ophthalmic device material comprises from 0.01 to 0.1% (w/w) of the azo compound of claim 1 .

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 of claim 1 .

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 9 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 the azo compound of claim 1 .

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

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

17. An intraocular lens comprising the azo compound of claim 4 .

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

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.