UV-absorbers for ophthalmic lens materials

1. A 1,4-disubstituted-1,2,3-triazole compound of the formula

where

x is 1-12;

Y is H, CH 3 , CH 2 OH, or CH 3 CH 2 ;

Z is O, NH, N(CH 3 ), or N(CH 2 CH 3 );

Z′ is O, NH, N(CH 3 ), or N(CH 2 CH 3 );

R″ is H, F, Cl, Br, I, O(CH 2 ) x H, NH 2 , NH(CH 3 ), N(CH 3 ) 2 , CH 3 , CH 2 CH 3 , CH(CH 3 ) 2 , C(CH 3 ) 3 , C 6 H 5 , or OC 6 H 5 ; and

R″′ is CH 2 ═CH—, CH 2 ═C(CH 3 )—, or

provided that one, but not both, of R and R′ is

2. The 1,4-disubstituted-1,2,3-triazole compound of claim 1 wherein the compound has the formula

where in formula [1]

x is 1-12;

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

Z is O, NH, N(CH 3 ), or N(CH 2 CH 3 ); and

R 2 is H, F, Cl, Br, I, O(CH 2 ) x H, NH 2 , NH(CH 3 ), N(CH 3 ) 2 , CH 3 , CH 2 CH 3 , CH(CH 3 ) 2 , C(CH 3 ) 3 , C 6 H 5 , or OC 6 H 5 .

3. The 1,4-disubstituted-1,2,3-triazole compound of claim 1 wherein the compound has the formula

where in formula [2]

R 3 is H, F, Cl, Br, I, O(CH 2 ) x H, NH 2 , NH(CH 3 ), N(CH 3 ) 2 , CH 3 , CH 2 CH 3 , CH(CH 3 ) 2 , C(CH 3 ) 3 , C 6 H 5 , or OC 6 H 5 ;

R 4 is

x is 1-12;

Y is H, CH 3 , or CH 3 CH 2 ; and

Z is O, NH, N(CH 3 ), or N(CH 2 CH 3 ).

4. An ophthalmic device material comprising the 1,4-disubstituted-1,2,3-triazole compound of claim 1 and a device-forming monomer selected from the group consisting of acrylic monomers and silicone-containing monomers.

5. The ophthalmic device material of claim 4 wherein the ophthalmic device material comprises from 0.1 to 5% (w/w) of the 1,4-disubstituted-1,2,3-triazole compound.

6. The ophthalmic device material of claim 5 wherein the ophthalmic device material comprises from 0.5 to 3% (w/w) of the 1,4-disubstituted-1,2,3-triazole compound.

7. The ophthalmic device material of claim 4 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 (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 [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.

9. The ophthalmic device material of claim 8 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.

10. The ophthalmic device material of claim 4 wherein the ophthalmic device material comprises a cross-linking agent.

11. The ophthalmic device material of claim 4 wherein the ophthalmic device material comprises a reactive blue-light absorbing compound.

12. An intraocular lens comprising the 1,4-disubstituted-1,2,3-triazole compound of claim 1 .

13. An intraocular lens comprising the 1,4-disubstituted-1,2,3-triazole compound of claim 2 .

14. An intraocular lens comprising the 1,4-disubstituted-1,2,3-triazole compound of claim 3 .

15. An ophthalmic device comprising the ophthalmic device material of claim 4 .

16. The ophthalmic device of claim 15 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.