Hydroxyphenyl phenanthrolines as polymerizable blockers of high energy light
Described are high energy light blocking compounds and ophthalmic devices containing the compounds. In particular, described are hydroxyphenyl phenanthroline structures with polymerizable functionality that block high energy light and are visibly transparent. The hydroxyphenyl phenanthroline structures can be incorporated into ophthalmic devices, such as hydrogel contact lenses, to protect eyes from high energy light radiation.
1. A compound of formula I:
wherein:
R 1 at each occurrence is independently H, halo, C 1 -C 6 alkyl, C 3 -C 12 cycloalkyl, aryl, or aryl-C 1 -C 6 -alkyl;
at least one R 2 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 are independently at each occurrence R g -L, H, C 1 -C 6 alkyl, C 3 -C 12 cycloalkyl, aryl, or aryl-C 1 -C 6 -alkyl,
wherein each alkyl, cycloalkyl, and aryl group is unsubstituted or substituted.
2. The compound of claim 1 wherein R 1 is at each occurrence is independently H or halo.
3. The compound of claim 1 wherein one R 2 is H and remaining R 2 are independently H, C 1 -C 6 alkyl, or Rg-L.
4. The compound of claim 1 wherein Rg comprises styryl, vinyl carbonate, vinyl ether, vinyl carbamate, N-vinyl lactam, N-vinylamide, (meth)acrylate, or (meth)acrylamide.
5. The compound of claim 1 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.
6. The compound of claim 1 that is selected from: 2-(2-(3-(tert-butyl)-4-hydroxy-5-(1,10-phenanthrolin-2-yl)phenyl)acetoxy)ethyl methacrylate; 2-(2-(4-hydroxy-3-(1,10-phenanthrolin-2-yl)phenyl)acetoxy)ethyl methacrylate; 2-(2-(3-(tert-butyl)-4-hydroxy-5-(1,10-phenanthrolin-2-yl)phenyl)acetamido)ethyl methacrylate; and 2-(2-(4-hydroxy-3-(1,10-phenanthrolin-2-yl)phenyl)acetamido)ethyl methacrylate.
7. An ophthalmic device comprising a free radical reaction product of the compound of claim 1 and one or more monomers suitable for making the ophthalmic device.
8. The ophthalmic device of claim 7 wherein the monomer suitable for making the ophthalmic device comprises a hydrophilic monomer, a silicone-containing component, or mixtures thereof.
9. The ophthalmic device of claim 7 that is a contact lens, a corneal onlay, a corneal inlay, an intraocular lens, or an overlay lens.
10. A hydrogel formed from a reactive mixture comprising: the compound of claim 1 ; and one or more monomers suitable for making the hydrogel.
11. The hydrogel of claim 10 wherein the monomer suitable for making the hydrogel comprises a hydrophilic monomer, a silicone-containing component, or mixtures thereof.
12. The hydrogel of claim 10 wherein the monomer suitable for making the hydrogel comprises a hydrophilic monomer and a silicone-containing component.
13. A contact lens comprising the hydrogel of claim 10 .
14. A method for making an ophthalmic device, the method comprising:
(a) providing a reactive mixture containing the compound of claim 1 , one or more monomers, and a radical initiator; and
(b) polymerizing the reactive mixture to form the ophthalmic device.
15. A compound that is 2-(3-(tert-butyl)-4-hydroxy-5-(1,10-phenanthrolin-2-yl)phenyl)acetic acid or salt thereof.