CONTACT LENSES AND METHODS OF MAKING CONTACT LENSES
Contact lenses with hydrophilic polymer coatings are described herein along with methods of making such lenses. The contact lenses can include a lens core that comprises about 75% to about 100% silicone. The hydrophilic polymer coating can include polyethylene glycol and polyacrylamide.
1 . A contact lens comprising:
a. a contact lens core comprising about 75% to about 100% silicone and;
b. a coating layer covalently attached to at least a portion of an outer surface of the contact lens core, the coating layer adapted to contact an ophthalmic surface, wherein the coating layer comprises a cross-linked, hydrophilic polymer, wherein the contact lens has an oxygen permeability Dk greater than 200*10̂-11 (cm/sec)(ml 02/m1 x mm Hg).
2 . The lens of claim 1 , wherein the contact lens core comprises about 98% to about 100% silicone.
3 . The lens of claim 1 , wherein the contact lens core consists of silicone.
4 . The lens of claim 1 , wherein the contact lens has an oxygen permeability Dk greater than 250*10̂-11 (cm/sec)(ml O2/ml×mm Hg).
5 . The lens of claim 1 , wherein the contact lens has an oxygen permeability Dk greater than 300*10̂-11 (cm/sec)(ml O2/ml×mm Hg).
6 . The lens of claim 1 , wherein a surface of the contact lens has an advancing contact angle<65 degrees.
7 . The lens of claim 1 , wherein a surface of the contact lens has an advancing contact angle<60 degrees.
8 . The lens of claim 1 , wherein a surface of the contact lens has an advancing contact angle between<55 degrees.
9 . The lens of claim 1 , wherein a surface of the contact lens has an advancing contact angle<50 degrees.
10 . The lens of claim 1 , wherein a surface of the contact lens has an advancing contact angle<45 degrees.
11 . The lens of claim 1 , wherein the contact lens surface has an advancing contact angle<40 degrees.
12 . The lens of claim 1 , wherein the contact lens surface has an advancing contact angle<35 degrees.
13 . The lens of claim 1 , wherein the contact lens surface has an advancing contact angle<30 degrees.
14 . The lens of claim 1 , wherein the coating layer and core are covalently attached at the outer surface by an amine moiety.
15 . The lens of claim 1 , wherein the coating layer and core are covalently attached at the outer surface by an epoxide moiety.
16 . The lens of claim 1 , wherein the hydrophilic polymer comprises a first polymer species with a reactive sulfonyl group and a second polymer species with a reactive thiol, and the first polymer species and second polymer species are cross-linked by a thioether linkage.
17 . The lens of claim 1 , wherein the hydrophilic polymer comprises a first polymer species with a reactive sulfonyl group and a second polymer species with a reactive amine, and the first polymer species and second polymer species are cross-linked by a aminoether linkage.
18 . The lens of claim 1 , wherein the coating layer substantially surrounds an outer surface of the core.
19 . The lens of claim 1 , wherein the coating layer and core are substantially optically clear.
20 . The lens of claim 1 , wherein the coating layer is adapted to allow optical transmission through the coating layer to the ophthalmic surface.
21 . The lens of claim 1 , wherein the coating layer comprises a thickness between about 5 nm to about 30 nm.
22 . The lens of claim 1 , wherein the coating layer comprises a thickness between about 10 nm to about 50 nm.
23 . The lens of claim 1 , wherein the coating layer has a maximum thickness of less than about 10 microns.
24 . The lens of claim 1 , wherein a first portion of the coating layer comprises a first thickness different from a second thickness of a second portion of the coating layer.
25 . The lens of claim 1 , wherein the hydrophilic polymer comprises a branched species having a branch count between two to twelve branch arms.
26 . The lens of claim 1 , wherein the hydrophilic polymer includes a polymer species with a reactive electron pair accepting group and a polysaccharide species with a reactive nucleophilic group, the reactive electron pair accepting group and the reactive nucleophilic group adapted to react to thereby form cross-links between the polymer species to the polysaccharide species.
27 . The lens of claim 26 , wherein the reactive electron pair accepting group is a sulfonyl moiety.
28 . The lens of claim 26 , wherein the reactive nucleophilic group is an amine moiety.
29 . The lens of claim 26 , wherein the reactive electron pair accepting group of the polysaccharide species is covalently linked to the outer surface of the core.
30 . The lens of claim 1 , wherein the coating layer comprises between about 80% to about 98% water by weight.
31 . The lens of claim 1 , wherein the hydrophilic polymer comprises polyethylene glycol.
32 . The lens of claim 1 , wherein the hydrophilic polymer comprises polyacrylamide.
33 . The lens of claim 1 , wherein the hydrophilic polymer comprises a polysaccharide.
34 . The lens of claim 33 , wherein the polysaccharide comprises Chondroitin.
35 . The lens of claim 33 , wherein the polysaccharide comprises Chondroitin sulfate.
36 . The lens of claim 33 , wherein the polysaccharide comprises Dextran.
37 . The lens of claim 33 , wherein the polysaccharide comprises Dextran sulfate.
38 . The lens of claim 33 , wherein the polysaccharide comprises Hydroxyl propyl methyl cellulose.
39 . A method of coating a contact lens core comprising:
a. Reacting an outer surface of the contact lens core with a first polymer species of a hydrophilic polymer solution, wherein the lens core is about 75% to about 100% silicone, wherein the first polymer species comprises an electron pair accepting moiety and a first portion of the electron pair accepting moiety forms a covalent attachment to the outer surface of the contact lens through a first nucleophilic conjugate reaction; and
b. Reacting the first polymer species of the hydrophilic polymer solution with a second polymer species of the hydrophilic polymer solution, the second polymer species comprising a nucleophilic reactive moiety adapted to covalently link to a second portion of the electron pair accepting moiety of the first polymer species in a second nucleophilic conjugate reaction to thereby at least partially cross-link the first and second polymer species, wherein a polymer hydrogel coating is formed and covalently attached to the outer surface of the contact lens core by the first and second nucleophilic conjugate reactions.
40 . The method of claim 39 , further comprising modifying an outer surface of the lens core to form a plurality of chemically reactive nucleophilic sites on the outer surface.
41 . The method of claim 39 , further comprising modifying an outer surface of the lens core to form a plurality of moieties that physically attract the polymer species to the lens surface.
42 . The method of claim 39 , further comprising modifying an outer surface of the lens core to form a combination of a plurality of chemically reactive sites as well as a plurality of physically attractive sites on the outer surface.
43 . The method of claim 39 , further comprising exposing the outer surface of the contact lens to a gas plasma treatment.
44 . The method of claim 40 , wherein the reactive nucleophilic sites on the outer surface include amines.
45 . The method of claim 41 , wherein the moieties on the outer surface include carboxylic acids.
46 . The method of claim 39 , further comprising modifying an outer surface of the lens core, wherein modifying includes the addition of an activator to a chemical mix used to form the lens core.
47 . The method of claim 46 , wherein the activator participates in a radical polymerization process of the chemical mix during fabrication of the lens core.
48 . The method of claim 46 , wherein the activator is a bifunctional polyethylene glycol.
49 . The method of claim 48 , wherein at least one moiety of the bifunctional activator does not participate in the radical polymerization process of the core lens during fabrication.
50 . The method of claim 46 , wherein the activator covalently bonds to a silane backbone of the lens core.
51 . The method of claim 46 , wherein the activator is N-(3-Aminopropyl)methacrylamide hydrochloride.
52 . The method of claim 39 , wherein reacting an outer surface of the contact lens with the first polymer species comprises reacting at least a portion of the plurality of reactive nucleophilic sites on the outer surface with a first portion of the electron pair accepting moiety on the first polymer species.
53 . The method of claim 39 , wherein the nucleophilic conjugate reactions are 1,4-nucleophilic addition reactions.
54 . The method of claim 39 , wherein the nucleophilic conjugate reactions are Michael-type reactions.
55 . The method of claim 39 , wherein the nucleophilic conjugate reactions are click reactions.
56 . The method of claim 39 , wherein the nucleophilic reactive moiety of the second polymer species is a thiol group and the electron pair accepting moiety of the first polymer species is a sulfonyl group.
57 . The method of claim 39 , wherein the first polymer species and the second polymer species are cross-linked through an aminoether moiety.
58 . The method of claim 39 , wherein the nucleophilic reactive moiety of the second polymer species is an amine group and the electron pair accepting moiety of the first polymer species is a sulfonyl group.
59 . The method of claim 39 , wherein the first polymer species and the second polymer species are cross-linked through an aminoether moiety.
60 . The method of claim 39 , wherein the nucleophilic reactive moiety of the second polymer species is an amine group and the electron pair accepting moiety of the polysaccharide species is a sulfonyl group.
61 . The method of claim 39 , wherein the first polymer species and the polysaccharide species are cross-linked through an aminoether moiety.
62 . The method of claim 39 , wherein the hydrophilic polymer solution comprises substantially equivalent concentrations of the reactive moieties of the first polymer species and second polymer species.
63 . The method of claim 39 , wherein the concentrations of the reactive moieties of the first polymer species exceeds the concentration of the nucleophilic reactive moiety of the second polymer species by about 1% to about 50%.
64 . The method of claim 39 , wherein the reacting steps are performed at a temperature between about 15 degrees Celsius and about 60 degrees Celsius.
65 . The method of claim 39 , wherein the reacting steps are performed at a temperature of 120 degrees Celsius and 17 barr pressure
66 . The method of claim 39 , wherein the reacting steps are performed at a pH between about 7 and about 12.
67 . The method of claim 39 , wherein the polymer hydrogel coating is substantially optically clear.
68 . The method of claim 39 , wherein the contact lens comprises a core consisting of silicone.