UV-absorbers for ophthalmic lens materials

1. A UV absorber of the formula

wherein

R 1 and R 3 independently=H; C 1 -C 12 alkyl, optionally substituted; C 1 -C 12 cycloalkyl, optionally substituted; phenyl, optionally substituted; or naphthyl; or R 1 and R 3 are linked through the optional (as designated by the dashed bonds) linking group R 2 where R 2 is a C 1 -C 6 alkylene, optionally substituted; or R 1 , R 2 , and R 3 taken together form an optionally substituted 1,2-phenyl, 1,2-naphthyl, or 2,3-naphthyl, wherein, in each case, the optional substituents are independently C 1 -C 6 alkyl, C 1 -C 6 alkoxy, OH, —Si(CH 3 ) 3 , halogen, —(CH 2 CH 2 O) n —R 10 , or —(CH 2 CH(CH 3 )O) n R 10 ;

R 10 =H, —Si(CH 3 ) 3 , or C 1 -C 6 alkyl;

R 8 =H or C 1 -C 12 alkyl; and

R 9 =H; C 1 -C 12 alkyl, optionally substituted with OH; or

R 4 =C 1 -C 12 alkylene, (CH 2 CH 2 O) n , (CH 2 CH(CH 3 )O) n , or CH 2 CH 2 CH 2 (Si(CH 3 ) 2 O) m Si(CH 3 ) 2 CH 2 CH 2 CH 2 ;

X=nothing, O, NR 7 , or S, provided that if R 4 is (CH 2 CH 2 O) n , or (CH 2 CH(CH 3 )O) n then X is nothing;

R 5 =nothing, C(═O), C(═O)C j H 2j , C 1 -C 6 alkylene, phenyl, or C 1 -C 6 alkylphenyl; C(═O)O, C(═O)OC j H 2j , C(═O)NR 7 , C(═O)NR 7 C j H 2j , C(═S)O, C(═S)OC j H 2j , C(═S)NR 7 , C(═S)NR 7 C j H 2j ,

n=2-10;

j=1-6;

m=1-9;

R 6 =H or methyl; and

R 7 =H, C 1 -C 6 alkyl, or phenyl.

2. The UV absorber of claim 1 wherein

R 1 and R 3 independently=C 1 -C 4 alkyl or phenyl;

R 2 =nothing;

R 9 =

R 4 is C 1 -C 6 alkylene;

X is O or NR 7 ;

R 5 is C(═O) or C 1 -C 6 alkylphenyl;

R 6 is H or methyl;

R 7 is H; and

R 8 is C 4 -C 12 t-alkyl.

3. The UV absorber of claim 2 wherein:

R 1 and R 3 =methyl;

R 2 =nothing;

R 9 =

R 4 is C 2 -C 3 alkylene;

X is O;

R 5 is C(═O),

R 6 is H or methyl;

R 7 is H; and

R 8 is t-butyl.

4. The UV absorber of claim 1 wherein the UV absorber is N-2-[2′-Hydroxy-3′-tert-butyl-5′-(3″-methacryloyloxypropoxy)phenyl]-5,6-dimethoxy-2H-benzotriazole.

5. An ophthalmic device material comprising the UV absorber 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 0.1 to 5% (w/w) of the UV absorber of claim 1 .

7. The ophthalmic device material of claim 6 wherein the ophthalmic device material comprises from 0.1 to 2% (w/w) of the UV absorber of claim 1 .

8. 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.

9. The ophthalmic device material of claim 8 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.

10. 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.

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

12. The ophthalmic device material of claim 5 wherein the ophthalmic device material comprises a reactive blue-light absorbing compound.

13. An intraocular lens comprising the UV absorber of claim 1 .

14. An intraocular lens comprising the UV absorber of claim 2 .

15. An intraocular lens comprising the UV absorber of claim 3 .

16. An intraocular lens comprising the UV absorber of claim 4 .

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.