High refractive index ophthalmic device materials
View Patent ↗High refractive index copolymers suitable for use in ophthalmic devices are disclosed. The copolymers comprise a single aryl hydrophobic monomer as a device forming monomer. In addition, the copolymers comprise a non-polymerizable block copolymer surfactant. The copolymers have a reduced tendency to form glistenings when stored in water at physiological temperatures.
1. An ophthalmic device material comprising
a) device-forming monomers consisting essentially of a single polymerizable monomer of the structure:
wherein:
Z is H or CH 3 ;
X is (CH2) m or O(CH 2 CH 2 O) n ;
m is 2-6;
n is 1-6; and
Ar is phenyl which can be unsubstituted or substituted with CH3, C2H5, n-C3H7, iso-C3H7, OCH3, C6H11, Cl, Br, C6H5, or CH2C6H5;
b) a polymerizable cross-linking agent; and
c) a non-polymerizable block copolymer surfactant selected from the group consisting of: a propylene oxide-ethylene oxide-propylene oxide block copolymer surfactant having an average molecular weight of approximately 3600 and an ethylene oxide unit content of approximately 40% by weight, and an ethylene oxide-propylene oxide-ethylene oxide block copolymer surfactant having an average molecular weight of approximately 5900 and a ethylene oxide unit content of approximately 40% by weight.
2. The ophthalmic device material of claim 1 wherein the monomer of structure (I) is selected from the group consisting of: 2-phenoxyethyl acrylate; 3-phenoxypropyl acrylate; 4-phenoxybutyl acrylate; polyethylene glycol phenyl ether acrylate; and their corresponding methacrylates.
3. The ophthalmic device material of claim 1 wherein X is (CH 2 ) m ; m is 2-4; and Ar is phenyl.
4. The ophthalmic device material of claim 3 wherein the single monomer of structure (I) is 2-phenyloxyethyl acrylate.
5. The ophthalmic device material of claim 1 wherein the amount of monomer of structure (I) is at least 75% by weight.
6. The ophthalmic device material of claim 5 wherein the amount of monomer of structure (I) is 80-90% by weight.
7. The ophthalmic device material of claim 6 wherein the amount of monomer of structure (I) is 87-90% by weight.
8. The ophthalmic device material of claim 5 wherein the amount of non-polymerizable block copolymer surfactant is 5-15% by weight.
9. The ophthalmic device material of claim 8 wherein the amount of non-polymerizable block copolymer surfactant is 9-11% by weight.
10. The ophthalmic device material of claim 1 wherein the non-polymerizable block copolymer surfactant is a propylene oxide-ethylene oxide-propylene oxide block copolymer surfactant having an average molecular weight of approximately 3600 and an ethylene oxide unit content of approximately 40% by weight.
11. The ophthalmic device material of claim 1 wherein the non-polymerizable block copolymer surfactant is an ethylene oxide-propylene oxide-ethylene oxide block copolymer surfactant having an average molecular weight of approximately 5900 and an ethylene oxide unit content of approximately 40% by weight.
12. The ophthalmic device material of claim 1 further comprising an ultraviolet absorbing compound.
13. The ophthalmic device material of claim 1 further comprising a yellow dye.
14. An ophthalmic device comprising the ophthalmic device material of claim 1 , wherein the ophthalmic device is selected from the group consisting of: intraocular lenses; contact lenses; keratoprostheses; intracorneal lenses; and corneal inlays or rings.