Method for producing contact lenses with durable lubricious coatings thereon

Patent metadata

Field	Value
Publication number	US-2017068019-A1
Application number	US-201615249587-A
Country	US
Kind code	A1
Filing date	Aug 29, 2016
Priority date	Sep 4, 2015
Publication date	Mar 9, 2017
Grant date	—

Abstract

The invention is related to a method for producing silicone hydrogel contact lenses with a stable lubricious hydrogel coating thereon. A method of the invention comprises forming a plasma-reactive hydrophilic polymer hybrid base coating having reactive functional groups on a silicone hydrogel contact lens and heating the silicone hydrogel contact lens with the hybrid base coating in an aqueous solution of a water-soluble and thermally crosslinkable hydrophilic polymeric material to form a stable lubricious hydrogel coating thereon.

First claim

What is claimed is:

1 . A method for producing soft contact lenses, comprising the steps of:
(1) obtaining a preformed silicone hydrogel contact lens in a dry state; (2) subjecting the preformed silicone hydrogel contact lens in the dry state to a surface treatment to obtain a silicone hydrogel contact lens with a base coating thereon, wherein the base coating comprises a prime plasma layer, a reactive polymer layer on top of the prime plasma layer, and reactive functional groups selected from the group consisting of carboxyl groups, primary amino groups, secondary amino groups, and combinations thereof, wherein the surface treatment comprises the sub-steps of
(a) plasma-treating the surface of the preformed silicone hydrogel contact lens in the dry state with a plasma to obtain a silicone hydrogel contact lens with the prime plasma layer thereon, wherein the plasma is generated in a plasma gas composed of air, N 2 , O 2 , CO 2 , or a mixture of a C 1 -C 6 hydrocarbon and a secondary gas selected from the group consisting of air, N 2 , O 2 , CO 2 , and combinations thereof, wherein the prime plasma layer has a thickness of from about 0.5 nm to about 40 nm, and
(b) contacting the silicone hydrogel contact lens with the prime plasma layer thereon with a first aqueous solution including a reactive hydrophilic polymer having multiple reactive functional groups selected from the group consisting of carboxyl groups, primary amino groups, secondary amino groups, and combinations thereof to form the base coating which include the reactive polymer layer of the reactive hydrophilic polymer on top of the prime plasma layer; and
(3) heating the silicone hydrogel contact lens with the base coating thereon obtained in step (2), in a second aqueous solution which comprises a water-soluble and thermally-crosslinkable hydrophilic polymeric material having azetidinium groups and optionally primary or secondary amino groups and/or carboxyl groups, at a temperature of from about 60° C. to about 140° C. for a time period sufficient long to crosslink the water-soluble thermally-crosslinkable hydrophilic polymeric material and the base coating so as to form a hydrogel coating on the silicone hydrogel contact lens, wherein the silicone hydrogel contact lens in fully hydrated state has a WBUT of at least about 10 seconds and a friction rating of about 3 or lower.

2 . The method of claim 1 , wherein the plasma is generated in a plasma gas compose of CO 2 , or a mixture of methane and CO 2 .

3 . The method of claim 1 , wherein the first aqueous solution has a pH from about 1.0 to about 3.0, and wherein the reactive hydrophilic polymer is a polyanionic polymer comprising carboxyl groups and having a weight average molecular weight of at least 1000 Daltons.

4 . The method of claim 3 , wherein the polyanionic polymer is selected from the group consisting of polyacrylic acid, polymethacrylic acid, polyethylacrylic acid, poly(acrylic acid-co-methacrylic acid), poly(acrylic acid-co-ethacrylic acid), poly(methacrylic acid-co-ethacrylic acid), and a mixture thereof.

5 . The method of claim 1 , wherein the first aqueous solution has a pH from about 9.5 to about 11.0, wherein the reactive hydrophilic polymer is a polycationic polymer comprising primary and/or secondary amino groups and having a weight average molecular weight of at least 1000 Daltons.

6 . The method of claim 5 , wherein the polycationic polymer is selected from the group consisting of polyethyleneimine, polyallylamine, polyvinylamine, polyamidoamine, and a mixture thereof.

7 . The method of claim 1 , wherein the reactive hydrophilic polymer comprises azetidinium groups and reactive functional groups selected from the group consisting of primary groups, secondary amino groups, carboxyl groups, and combinations thereof, wherein the reactive hydrophilic polymer has a weight average molecular weight of at least 1000 Daltons, wherein the first aqueous solution has a pH of less than about 8.0.

8 . The method of claim 7 , wherein the reactive hydrophilic polymer is a chemically-modified poly(2-oxazoline-co-ethyleneimine)-epichlorohydrin, a chemically-modified polyamidoamine-epichlorohydrin, or combinations thereof, wherein the chemically-modified poly(2-oxazoline-co-ethyleneimine)-epichlorohydrin or the chemically-modified polyamidoamine-epichlorohydrin comprises (i) from about 20% to about 95% by weight of first polymer chains derived from a polyamidoamine-epichlorohydrin or a poly(2-oxazoline-co-ethyleneimine)-epichlorohydrin, (ii) from about 5% to about 80% by weight of hydrophilic moieties or second polymer chains derived from at least one hydrophilicity-enhancing agent having at least two reactive functional groups selected from the group consisting of amino group, carboxyl group, and combination thereof, wherein the hydrophilic moieties or second polymer chains are covalently attached to the first polymer chains through one or more covalent linkages each formed between one azetitdinium group of the polyamidoamine-epichlorohydrin or the poly(2-oxazoline-co-ethyleneimine)-epichlorohydrin and one amino, carboxyl or thiol group of the hydrophilicity-enhancing agent, and (iii) azetidinium groups which are parts of the first polymer chains or pendant or terminal groups covalently attached to the first polymer chains.

9 . The method of claim 1 , wherein the water-soluble thermally crosslinkable hydrophilic polymeric material is a poly(2-oxazoline-co-ethyleneimine)-epichlorohydrin, a chemically-modified poly(2-oxazoline-co-ethyleneimine)-epichlorohydrin, a chemically-modified polyamidoamine-epichlorohydrin, or combinations thereof, wherein the chemically-modified poly(2-oxazoline-co-ethyleneimine)-epichlorohydrin or the chemically-modified polyamidoamine-epichlorohydrin comprises (i) from about 20% to about 95% by weight of first polymer chains derived from a polyamidoamine-epichlorohydrin or a poly(2-oxazoline-co-ethyleneimine)-epichlorohydrin, (ii) from about 5% to about 80% by weight of hydrophilic moieties or second polymer chains derived from at least one hydrophilicity-enhancing agent having at least one reactive functional group selected from the group consisting of amino group, carboxyl group, thiol group, and combination thereof, wherein the hydrophilic moieties or second polymer chains are covalently attached to the first polymer chains through one or more covalent linkages each formed between one azetitdinium group of the polyamidoamine-epichlorohydrin or the poly(2-oxazoline-co-ethyleneimine)-epichlorohydrin and one amino, carboxyl or thiol group of the hydrophilicity-enhancing agent, and (iii) azetidinium groups which are parts of the first polymer chains or pendant or terminal groups covalently attached to the first polymer chains.

10 . The method of claim 9 , wherein the water-soluble thermally crosslinkable hydrophilic polymeric material is a chemically-modified poly(2-oxazoline-co-ethyleneimine)-epichlorohydrin or a chemically-modified polyamidoamine-epichlorohydrin, wherein the chemically-modified poly(2-oxazoline-co-ethyleneimine)-epichlorohydrin and the chemically-modified polyamidoamine-epichlorohydrin independently of each other comprise:
(i) from about 20% to about 95% by weight of first polymer chains derived from a polyamidoamine-epichlorohydrin or a poly(2-oxazoline-co-ethyleneimine)-epichlorohydrin; (ii) from about 5% to about 80% by weight of hydrophilic moieties or second polymer chains derived from at least one hydrophilicity-enhancing agent having at least one reactive functional group selected from the group consisting of amino group, carboxyl group, thiol group, and combination thereof; and (iii) positively-charged azetidinium groups which are parts of the f

Assignees

• Novartis Ag

Inventors

• Qian Xinming
• Chang Frank
• Matsuzawa Yasuo
• Shankar Venkat

Classifications

• C08J2383/08

  containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen · CPC title

• C08J2433/02

  Homopolymers or copolymers of acids; Metal or ammonium salts thereof · CPC title

• C08J7/123

  Treatment by wave energy or particle radiation (C08J7/18 takes precedence) · CPC title

• B29D11/00125

  Auxiliary operations, e.g. removing oxygen from the mould, conveying moulds from a storage to the production line in an inert atmosphere · CPC title

• C08J2471/00

  Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers · CPC title