Polymerizable blockers of high energy light
Described are high energy light blocking compounds and ophthalmic devices containing the compounds. In particular, described are hydroxybiphenyl benzotriazole structures with polymerizable functionality that block high energy light and are visibly transparent. The hydroxybiphenyl benzotriazole structures can be incorporated into ophthalmic devices, such as hydrogel contact lenses, to protect eyes from high energy light radiation.
1. A compound selected from: 2-(3-(5-(2H-benzo[d][1,2,3]triazol-2-yl)-6-hydroxy-[1,1′-biphenyl]-3-yl)propanamido)ethyl methacrylate, 2-(3-(3′-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-2′-hydroxy-[1,1′-biphenyl]-4-yl)propanamido)ethyl methacrylate, and 2-(3-(5′-(tert-butyl)-3′-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-2′-hydroxy-[1,1′-biphenyl]-4-yl)propanamido)ethyl methacrylate.
2. An ophthalmic device comprising a free radical reaction product of:
a compound of formula I:
wherein:
R 1 at each occurrence is independently H, halo, amino, or hydroxyl; and at least one of R 2 or R 3 is a group of formula R g -L, wherein R g is a polymerizable group and L is a linking group, and the remaining R 2 and R 3 are independently at each occurrence R g -L, H, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, or C 3 -C 7 cycloalkyl, wherein each alkyl and cycloalkyl may be unsubstituted or substituted; and
one or more monomers suitable for making the ophthalmic device.
3. The ophthalmic device of claim 2 wherein the monomer suitable for making the ophthalmic device comprises a hydrophilic monomer, a silicone-containing component, or mixtures thereof.
4. The ophthalmic device of claim 2 that is a contact lens, a corneal onlay, a corneal inlay, an intraocular lens, or an overlay lens.
5. A hydrogel formed from a reactive mixture comprising: a compound of formula I:
wherein:
R 1 at each occurrence is independently H, halo, amino, or hydroxyl; and at least one of R 2 or R 3 is a group of formula R g -L, wherein R g is a polymerizable group and L is a linking group, and the remaining R 2 and R 3 are independently at each occurrence R g -L, H, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, or C 3 -C 7 cycloalkyl, wherein each alkyl and cycloalkyl may be unsubstituted or substituted; and
one or more monomers suitable for making the hydrogel.
6. The hydrogel of claim 5 wherein the monomer suitable for making the hydrogel comprises a hydrophilic monomer, a silicone-containing component, or mixtures thereof.
7. The hydrogel of claim 5 wherein the monomer suitable for making the hydrogel comprises a hydrophilic monomer and a silicone-containing component.
8. A contact lens comprising the hydrogel of claim 5 .
9. A method for making the ophthalmic device of claim 2 , the method comprising:
(a) providing a reactive mixture containing the compound of formula I, one or more monomers, and a radical initiator; and
(b) polymerizing the reactive mixture to form the ophthalmic device.
10. A composition selected from: 3-(5-(2H-benzo[d][1,2,3]triazol-2-yl)-6-hydroxy-[1,1′-biphenyl]-3-yl)propanoic acid, methyl 3-(3′-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-2′-hydroxy-[1,1′-biphenyl]-4-yl)propanoate, and methyl 3-(5′-(tert-butyl)-3′-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-2′-hydroxy-[1,1′-biphenyl]-4-yl)propanoate.
11. The ophthalmic device of claim 2 wherein R 1 is at each occurrence is independently H or halo.
12. The ophthalmic device of claim 2 wherein R 2 and R 3 at each occurrence are independently H, C 1 -C 6 alkyl, or Rg-L.
13. The ophthalmic device of claim 2 wherein Rg comprises styryl, vinyl carbonate, vinyl ether, vinyl carbamate, N-vinyl lactam, N-vinylamide, (meth)acrylate, or (meth)acrylamide.
14. The ophthalmic device of claim 2 wherein the linking group comprises C 1 -C 8 alkylene, C 1 -C 8 oxaalkylene, C 1 -C 8 thiaalkylene, C 1 -C 8 alkylene-carboxylate-C 1 -C 8 alkylene, C 1 -C 8 alkylene-amide-C 1 -C 8 alkylene, or C 1 -C 8 alkylene-amine-C 1 -C 8 alkylene.
15. The ophthalmic device of claim 2 wherein the compound of formula I is selected from: 2-(3-(5-(2H-benzo[d][1,2,3]triazol-2-yl)-6-hydroxy-[1,1′-biphenyl]-3-yl)propanamido)ethyl methacrylate, 2-(3-(3′-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-2′-hydroxy-[1,1′-biphenyl]-4-yl)propanamido)ethyl methacrylate, and 2-(3-(5′-(tert-butyl)-3′-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-2′-hydroxy-[1,1′-biphenyl]-4-yl)propanamido)ethyl methacrylate.