2-amino benzophenone UV-absorbers for ophthalmic lens materials

1. A polymeric ophthalmic device material formed by polymerizing a composition comprising

a) 0.1 to 5% (w/w) of a UV absorber of formula (I):

wherein in formula (I):

R is H, C 1 -C 4 alkyl, —C(═O)C(═CH 2 )X, or —C(═O)O—(CH 2 ) n O—C(═O)C(═CH 2 )X;

n is 1-6;

X is H, CH 3 , or CH 2 CH 3 ;

Y 1 , Y 2 independently are H, Br, Cl, F, I, OCH 3 , NO 2 , —C(═O)C(═CH 2 )X, or —C(═O)O—(CH 2 ) n O—C(═O)C(═CH 2 )X; and

Y 3 is H, Br, Cl, F, I, OCH 3 , or NO 2 ;

provided that no more than one of R, Y 1 , and Y 2 may be —C(═O)C(═CH 2 )X or —C(═O)O—(CH 2 ) n O—C(═O)C(═CH 2 )X; and

b) a device-forming monomer selected from the group consisting of acrylic monomers and silicone-containing monomers.

2. The ophthalmic device material of claim 1 wherein in formula (I)

R is H or C 1 -C 4 alkyl;

n is 1-6;

X is H, CH 3 , or CH 2 CH 3 ;

Y 1 , Y 2 independently are H, Br, Cl, F, I, OCH 3 , NO 2 , —C(═O)C(═CH 2 )X, or —C(═O)O—(CH 2 ) n O—C(═O)C(═CH 2 )X; and

Y 3 is Br, Cl, F, I, OCH 3 , or NO 2 ;

provided that no more than one of Y 1 and Y 2 may be —C(═O)C(═CH 2 )X or —C(═O)O—(CH 2 ) n O—C(═O)C(═CH 2 )X.

3. The ophthalmic device material of claim 2 wherein in formula (I)

R is H or C 1 -C 4 alkyl;

n is 1-6;

X is H or CH 3 ;

Y 1 , Y 2 independently are H, Br, Cl, F, I, OCH 3 , NO 2 , —C(═O)C(═CH 2 )X, or —C(═O)O—(CH 2 ) n O—C(═O)C(═CH 2 )X; and

Y 3 is Cl;

provided that no more than one of Y 1 and Y 2 may be —C(═O)C(═CH 2 )X or —C(═O)O—(CH 2 ) n O—C(═O)C(═CH 2 )X.

4. The ophthalmic device material of claim 1 wherein the UV absorber is selected from the group consisting of: 2-amino benzophenone, 2-amino-5-chloro benzophenone, and 2-methylamino-5-chloro benzophenone.

5. The ophthalmic device material of claim 1 wherein the composition comprises from 0.1 to 4% (w/w) of the UV absorber.

6. The ophthalmic device material of claim 5 wherein the composition comprises from 1 to 3% (w/w) of the UV absorber.

7. The ophthalmic device material of claim 1 wherein the composition comprises a device-forming monomer of formula [V]:

where in formula [V]:

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.

8. The ophthalmic device material of claim 7 wherein in formula [V]:

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.

9. The ophthalmic device material of claim 8 wherein the composition comprises a monomer selected from the group consisting of: 2-phenylethyl methacrylate, 4-phenylbutyl methacrylate, 5-phenylpentyl methacrylate, 2-benzyloxyethyl methacrylate, 3-benzyloxypropyl methacrylate, 2-phenylethyl acrylate, 4-phenylbutyl acrylate, 5-phenylpentyl acrylate, 2-benzyloxyethyl acrylate, and 3-benzyloxypropyl acrylate.

10. The ophthalmic device material of claim 1 wherein the composition comprises a cross-linking agent.

11. The ophthalmic device material of claim 1 wherein the composition comprises a reactive blue-light absorbing compound.

12. An ophthalmic device comprising an ophthalmic device material of claim 1 , 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.

13. The ophthalmic device of claim 12 wherein the ophthalmic device is an intraocular lens.