Extended wear ophthalmic lens

• US 8,568,626 B2
• Filed: 10/16/2008
• Issued: 10/29/2013
• Est. Priority Date: 09/06/1994
• Status: Expired due to Fees

• Current Assignee: Novartis Ag
• Original Assignee: CIBA Vision Corporation (Bayer AG)
• Inventors: Nicolson, Paul Clement, Baron, Richard Carlton, Chabrecek, Peter, Court, John, Domschke, Angelika, Griesser, Hans Jorge, Ho, Arthur, Hopken, Jens, Laycock, Bronwyn Glenice, Liu, Qin, Lohmann, Dieter, Meijs, Gordon Francis, Papaspiliotopoulos, Eric, Riffle, Judy Smith, Schindhelm, Klaus, Sweeney, Deborah, Terry, Wilson Leonard Jr., Vogt, Jurgen, Winterton, Lynn Cook
• Primary Examiner(s): SANDERS, JAMES M
• Application Number:
  US12/252,406
• Publication Number:
  US 20090039535A1
• Time in Patent Office: 1,839 Days
• Field of Search: 264/1.32, 264/2.5, 425/808
• US Class Current: 264/1.32
• CPC Class Codes: A61L 2430/16 for reconstruction of eye parts, e.g. intraocular lens, cornea
• CPC Class Codes: A61L 27/26 Mixtures of macromolecular compounds
• CPC Class Codes: A61L 27/34 Macromolecular materials
• CPC Class Codes: B05D 1/62 Plasma-deposition of organic layers plasma deposition in general C23C14/00, C23C16/00
• CPC Class Codes: B29C 39/42 Casting under special conditions, e.g. vacuum
• CPC Class Codes: B29C 71/00 After-treatment of articles without altering their shape; Apparatus therefor B29C44/56, B29C73/00 take precedence; surface shaping B29C59/00 ; for joined or sealed parts B29C66/03; after-treatment specially adapted for vulcanising tyres B29D30/0633
• CPC Class Codes: B29D 11/00076 enabling passage of fluids, e.g. oxygen, tears, between the area under the lens and the lens exterior
• CPC Class Codes: B29L 2011/0041 Contact lenses
• CPC Class Codes: C08G 18/10 Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
• CPC Class Codes: C08G 18/48 Polyethers
• CPC Class Codes: C08G 18/4833 Polyethers containing oxyethylene units
• CPC Class Codes: C08G 18/5015 having fluorine atoms
• CPC Class Codes: C08G 18/61 Polysiloxanes
• CPC Class Codes: C08G 18/63 Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers
• CPC Class Codes: C08G 18/672 Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
• CPC Class Codes: C08G 18/8116 esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group
• CPC Class Codes: C08G 18/8175 with esters of acrylic or alkylacrylic acid having only one group containing active hydrogen
• CPC Class Codes: C08L 33/00 Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 39/06 Homopolymers or copolymers of N-vinyl-pyrrolidones
• CPC Class Codes: C08L 51/08 grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
• CPC Class Codes: C08L 51/085 : on to polysiloxanes
• CPC Class Codes: C08L 83/04 : Polysiloxanes
• CPC Class Codes: G02B 1/043 : Contact lenses
• CPC Class Codes: G02C 7/049 : Contact lenses having special fitting or structural features achieved by special materials or material structures
• CPC Class Codes: Y10S 525/903 : Interpenetrating network
• CPC Class Codes: Y10S 525/936 : Encapsulated chemical agent
• CPC Class Codes: Y10S 525/937 : Utility as body contact e.g. implant, contact lens or I.U.D.

Abstract

A method for making a silicone hydrogel contact lens is provided. In one embodiment, a prepolymer mixture is polymerized in a lens mold in an atmosphere having less than about 10000 ppm oxygen to form a silicone hydrogel contact lens suitable for extended wear as characterized by producing less than 10% corneal swelling after a period of continuous wear of 7 days including normal sleep periods. In one embodiment, the prepolymer mixture comprises at least one oxyperm material containing hydrophilic groups, wherein the at least one oxyperm material is a siloxane-containing macromer or monomer, at least one ionoperm material, and a cross-linking agent. In certain embodiments, the polymerization of the prepolymer mixture may be carried out in an atmosphere having less than about 1000 ppm oxygen.

Claims

1. A method for making a silicone hydrogel contact lens, comprising a step of:

polymerizing a prepolymer mixture in a lens mold in an atmosphere having less than about 10000 ppm oxygen to form a silicone hydrogel contact lens suitable for extended wear as characterized by having on-eye movement with blinking and producing less than 10% corneal swelling after a period of continuous wear of 7 days including normal sleep periods,

wherein the prepolymer mixture comprises

(a) at least one oxyperm material containing hydrophilic groups, wherein the at least one oxyperm material is a siloxane-containing macromer or monomer;

(b) at least one ionoperm material selected from the group consisting of acrylates, 2-hydroxyethyl methacrylate, acrylamide, methacrylamide, dimethylacrylate, poly(ethyleneglycol), N-vinylpyrrolidone, and mixtures thereof, and

(c) a cross-linking agent, and the method further comprising

extracting the silicone hydrogel contact lens with a solvent to remove unreacted monomers, wherein the mold includes at least two mold halves.

2. The method of claim 1, wherein the polymerization of the prepolymer mixture is carried out in an atmosphere having less than about 1000 ppm oxygen.

3. The method of claim 1, wherein the method further comprises (1) degassing the prepolymer mixture, (2) filling the degassed prepolymer mixture in the mold, (3) sealing the mold halves to one another.

4. The method of claim 1, wherein the mold is stored in nitrogen.

5. The method of claim 1, wherein the crosslinking agent is selected from the group consisting of allyl(meth)acrylate, lower alkylene glycol di(meth)acrylate, poly lower alkylene glycol di(meth)acrylate, lower alkylene di(meth)acrylate, divinyl ether, divinyl sulfone, divinylbenzene, trivinylbenzene, trimethylolpropane tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, bisphenol A di(meth)acrylate, methylenebis(meth)acrylamide, triallyl phthalate, and diallyl phthalate.