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 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.
2 . The method of claim 1 , further comprising modifying an outer surface of the lens core to form a plurality of chemically reactive nucleophilic sites on the outer surface.
3 . The method of claim 1 , 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.
4 . The method of claim 1 , 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.
5 . The method of claim 1 , further comprising exposing the outer surface of the contact lens to a gas plasma treatment.
6 . The method of claim 2 , wherein the reactive nucleophilic sites on the outer surface include amines.
7 . The method of claim 3 , wherein the moieties on the outer surface include carboxylic acids.
8 . The method of claim 1 , 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.
9 . The method of claim 8 , wherein the activator participates in a radical polymerization process of the chemical mix during fabrication of the lens core.
10 . The method of claim 8 , wherein the activator is a bifunctional polyethylene glycol.
11 . The method of claim 10 , wherein at least one moiety of the bifunctional activator does not participate in the radical polymerization process of the core lens during fabrication.
12 . The method of claim 8 , wherein the activator covalently bonds to a silane backbone of the lens core.
13 . The method of claim 8 , wherein the activator is N-(3-Aminopropyl)methacrylamide hydrochloride.
14 . The method of claim 1 , 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.
15 . The method of claim 1 , wherein the nucleophilic conjugate reactions are 1,4-nucleophilic addition reactions.
16 . The method of claim 1 , wherein the nucleophilic conjugate reactions are Michael-type reactions.
17 . The method of claim 1 , wherein the nucleophilic conjugate reactions are click reactions.
18 . The method of claim 1 , 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.
19 . The method of claim 1 , wherein the first polymer species and the second polymer species are cross-linked through an aminoether moiety.
20 . The method of claim 1 , 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.
21 . The method of claim 1 , wherein the first polymer species and the second polymer species are cross-linked through an aminoether moiety.
22 . The method of claim 1 , 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.
23 . The method of claim 1 , wherein the first polymer species and the polysaccharide species are cross-linked through an aminoether moiety.
24 . The method of claim 1 , wherein the hydrophilic polymer solution comprises substantially equivalent concentrations of the reactive moieties of the first polymer species and second polymer species.
25 . The method of claim 1 , 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%.
26 . The method of claim 1 , wherein the reacting steps are performed at a temperature between about 15 degrees Celsius and about 60 degrees Celsius.
27 . The method of claim 1 , wherein the reacting steps are performed at a temperature of 120 degrees Celsius and 17 barr pressure
28 . The method of claim 1 , wherein the reacting steps are performed at a pH between about 7 and about 12.
29 . The method of claim 1 , wherein the polymer hydrogel coating is substantially optically clear.
30 . The method of claim 1 , wherein the contact lens comprises a core consisting of silicone.