Extended wear ophthalmic lens

• US 7,468,398 B2
• Filed: 06/07/2005
• Issued: 12/23/2008
• Est. Priority Date: 09/06/1994
• Status: Expired due to Fees

• Current Assignee: Novartis Ag
• Original Assignee: CIBA Vision Corporation (Bayer AG)
• Inventors: Court, John, Winterton, Lynn Cook, Ho, Arthur, Lohmann, Dieter, Chabrecek, Peter, Liu, Qin, Meijs, Gordon Francis, Schindhelm, Klaus, Laycock, Bronwyn Glenice, Domschke, Angelika, Nicolson, Paul Clement, Baron, Richard Carlton, Sweeney, Deborah, Terry, Wilson Leonard Jr., Hopken, Jens, Griesser, Hans Jorg, Vogt, Jurgen, Smith Riffle, Judy, Papspiliotopoulos, Eric
• Primary Examiner(s): Cain; Edward J
• Application Number:
  US11/146,586
• Publication Number:
  US 20050228065A1
• Time in Patent Office: 1,295 Days
• Field of Search: 523/106, 523/107, 523/108
• US Class Current: 523/107
• CPC Class Codes: A61L 27/26 Mixtures of macromolecular compounds
• 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: 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 2666/20 Macromolecular compounds having nitrogen in the main chain according to C08L75/00 - C08L79/00; Derivatives thereof
• 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 43/04 Homopolymers or copolymers of monomers containing silicon
• 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 75/04 Polyurethanes
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 : Contact lenses

Abstract

An ophthalmic lens suited for extended-wear periods of at least one day on the eye without a clinically significant amount of corneal swelling and without substantial wearer discomfort. The lens has a balance of oxygen permeability and ion or water permeability, with the ion or water permeability being sufficient to provide good on-eye movement, such that a good tear exchange occurs between the lens and the eye. A preferred lens is a copolymerization product of a oxyperm macromer and an ionoperm monomer. The invention encompasses extended wear contact lenses, which include a core having oxygen transmission and ion transmission pathways extending from the inner surface to the outer surface.

Claims

1. A contact lens comprising a polymeric material formed from a prepolymerization mixture including:

(a) at least one siloxane-containing macromer, wherein said at least one siloxane-containing macromer comprises at least two different hydrophilic groups and a poly(disubstituted siloxane) segment, wherein said hydrophilic groups are selected from the group consisting of polyoxyethylene, urethane, urea, amide, amine, hydroxyl and combinations thereof;

(b) at least one hydrophilic monomer selected from the group consisting of N, N-dimethylacrylamide, hydroxyl-substituted C₁-C₆ alkylacrylate, hydroxyl-substituted C₁-C₆ alkylmethacrylate, N-vinylpyrrolidone, and combinations thereof; and

(c) a cross-linking agent,

the contact lens characterized by having a tensile modulus of less than about 3.0 MPa and producing less than 10% corneal swelling after a period of wear of 7 days including normal sleep periods.

2. The contact lens of claim 1, wherein the cross-linking 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.

3. The contact lens of claim 1, wherein the at least one hydrophilic monomer comprises N-vinylpyrrolidone.

4. The contact lens of claim 1, wherein said at least one siloxane-containing macromer comprises a polydimethylsiloxane segment.

5. The contact lens of claim 4, wherein said at least one siloxane-containing macromer comprises a poly(di-substituted siloxane) segment which includes a substituent selected from the group consisting of a partly fluorinated alkyl, an aminoalkyl, an alkenyl, an aryl, a cyanoalkyl, a hydroxyalkyl, -alk-NH-alk-NH₂, -alk-(OCH₂CH₂)_m—

(OCH₂)_p—

OR₇, and combinations thereof, wherein alk is alkylene, R₇ is hydrogen or C₁-C₆ alkyl, m and p independently of one another are an integer from 0 to 10.

6. The contact lens of claim 5, wherein the tensile modulus is between about 0.5 to about 1.5 MPa.

7. The contact lens of claim 5, wherein the contact lens is coated with a layer of a hydrophilic polymeric material.

8. The contact lens of claim 5, wherein the prepolymerization mixture comprises at least one hydrophobic monomer selected from the group consisting of methyl acrylate, ethyl acrylate, propyl acrylate, isopropyl acrylate, isobutyl acrylate, isooctyl acrylate, isodecyl acrylate, cyclohexyl acrylate, 2-ethylhexyl acrylate, methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl acrylate, vinyl acetate, vinyl propionate, vinyl butyrate, vinyl valerate, styrene, chloroprene, vinyl chloride, vinylidene chloride, acrylonitrile, 1-butene, butadiene, methacrylonitrile, vinyl toluene, vinyl ethyl ether, perfluorohexylethylthiocarbonylaminoethyl methacrylate, isobomyl methacrylate, trifluoroethyl methacrylate, hexafluoroisopropyl methacrylate, hexafluorobutyl (meth)acrylate, tris-trimethylsilyloxy-silyl-propylmethacrylate, 3-methacryloxypropylpentamethyldisiloxane, bis(methacryloxypropyl) tetramethyldisiloxane and combinations thereof.

9. The contact lens of claim 8 wherein the hydrophobic monomer is isobomyl methacrylate or tris-trimethylsilyloxy-silyl-propyl methacrylate.

10. The contact lens of claim 8, wherein the hydrophilic monomer comprises N-vinylpyrrolidone.

11. The contact lens of claim 8 producing less than 7% corneal swelling after a period of wear of 7 days including normal sleep periods.

12. The contact lens of claim 8 producing less than 5% corneal swelling after a period of wear of 7 days including normal sleep periods.