Extended wear ophthalmic lens

• US 9,612,455 B2
• Filed: 09/23/2013
• Issued: 04/04/2017
• Est. Priority Date: 04/04/1995
• Status: Expired due to Fees

• Current Assignee: Novartis Ag
• Original Assignee: Novartis Ag
• Inventors: Terry, Jr., Wilson Leonard, 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, Vogt, Jurgen, Winterton, Lynn Cook
• Primary Examiner(s): Salamon, Peter A
• Application Number:
  US14/033,986
• Publication Number:
  US 20140022507A1
• Time in Patent Office: 1,289 Days
• Field of Search: None
• 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 ionperm 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 contact lens, comprising a polymeric material which is a polymerization product of a prepolymerization mixture including N-vinylpyrrolidone and at least one siloxane-containing macromer having a polydimethylsiloxane segment,

wherein the contact lens is characterized by having a lens center thickness of about 30 to about 200 microns, a tensile modulus of from about 0.5 to about 1.5 MPa and by producing less than 8% corneal swelling after a period of wear of about 24 hours including normal sleep periods, and

wherein the contact lens has an Ionoton Ion Permeability Coefficient of greater than about 0.3×

10<sup>−

6</sup> cm²/sec.

2. The contact lens of claim 1, wherein said prepolymerization mixture comprises a crosslinking agent 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 2, wherein said prepolymerization mixture further comprises N,N-dimethylacrylamide and/or hydroxyethylmethacrylate.

4. The contact lens of claim 1, wherein said prepolymerization mixture further comprises N,N-dimethylacrylamide and/or hydroxyethylmethacrylate.

5. The contact lens of claim 4, wherein said prepolymerization mixture further 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, isobornyl methacrylate, trifluoroethyl methacrylate, hexafluoroisopropyl methacrylate, hexafluorobutyl (meth)acrylate, tri s-trimethyl silyloxy-silyl-propyl methacrylate, 3-methacryloxypropylpentamethyldisiloxane, bis(methacryloxypropyl) tetramethyldisiloxane and combinations thereof.

6. The contact lens of claim 3, wherein said prepolymerization mixture further 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, isobornyl methacrylate, trifluoroethyl methacrylate, hexafluoroisopropyl methacrylate, hexafluorobutyl (meth)acrylate, tri s-trimethyl silyloxy-silyl-propyl methacrylate, 3-methacryloxypropylpentamethyldisiloxane, bis(methacryloxypropyl) tetramethyldisiloxane and combinations thereof.

7. The contact lens of claim 2, wherein said prepolymerization mixture further 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, isobornyl methacrylate, trifluoroethyl methacrylate, hexafluoroisopropyl methacrylate, hexafluorobutyl (meth)acrylate, tri s-trimethyl silyloxy-silyl-propyl methacrylate, 3-methacryloxypropylpentamethyldisiloxane, bis(methacryloxypropyl) tetramethyldisiloxane and combinations thereof.

8. A contact lens, comprising a polymeric material which is a polymerization product of a prepolymerization mixture including N-vinylpyrrolidone and at least one siloxane-containing macromer having a polydimethylsiloxane segment and, wherein the contact lens is characterized by having a lens center thickness of about 30 to about 200 microns, a tensile modulus of from about 0.5 to about 1.5 MPa and by producing less than 6% corneal swelling after a period of wear of about 24 hours including normal sleep periods, and

wherein the contact lens has an Ionoton Ion Permeability Coefficient of greater than about 0.3×

10<sup>−

6</sup> cm²/sec.

9. The contact lens of claim 8, wherein said prepolymerization mixture comprises a crosslinking agent 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.

10. The contact lens of claim 9, wherein said prepolymerization mixture further comprises N,N-dimethylacrylamide and/or hydroxyethylmethacrylate.

11. The contact lens of claim 8, wherein said prepolymerization mixture further comprises N,N-dimethylacrylamide and/or hydroxyethylmethacrylate.

12. The contact lens of claim 11, wherein said prepolymerization mixture further 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, isobornyl methacrylate, trifluoroethyl methacrylate, hexafluoroisopropyl methacrylate, hexafluorobutyl (meth)acrylate, tri s-trimethyl silyloxy-silyl-propyl methacrylate, 3-methacryloxypropylpentamethyldisiloxane, bis(methacryloxypropyl) tetramethyldisiloxane and combinations thereof.

13. The contact lens of claim 10, wherein said prepolymerization mixture further 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, isobornyl methacrylate, trifluoroethyl methacrylate, hexafluoroisopropyl methacrylate, hexafluorobutyl (meth)acrylate, tri s-trimethyl silyloxy-silyl-propyl methacrylate, 3-methacryloxypropylpentamethyldisiloxane, bis(methacryloxypropyl) tetramethyldisiloxane and combinations thereof.

14. The contact lens of claim 9, wherein said prepolymerization mixture further 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, isobornyl methacrylate, trifluoroethyl methacrylate, hexafluoroisopropyl methacrylate, hexafluorobutyl (meth)acrylate, tri s-trimethyl silyloxy-silyl-propyl methacrylate, 3-methacryloxypropylpentamethyldisiloxane, bis(methacryloxypropyl) tetramethyldisiloxane and combinations thereof.

15. A contact lens, comprising a polymeric material which is a polymerization product of a prepolymerization mixture including N-vinylpyrrolidone and at least one siloxane-containing macromer having a polydimethylsiloxane segment and, wherein the contact lens is characterized by having a lens center thickness of about 30 to about 200 microns, a tensile modulus of from about 0.5 to about 1.5 MPa and by producing less than 4% corneal swelling after a period of wear of about 24 hours including normal sleep periods, and

wherein the contact lens has an Ionoton Ion Permeability Coefficient of greater than about 0.3×

10<sup>−

6</sup> cm²/sec.

16. The contact lens of claim 15, wherein said prepolymerization mixture comprises a crosslinking agent 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.

17. The contact lens of claim 16, wherein said prepolymerization mixture further comprises N,N-dimethylacrylamide and/or hydroxyethylmethacrylate.

18. The contact lens of claim 15, wherein said prepolymerization mixture further comprises N,N-dimethylacrylamide and/or hydroxyethylmethacrylate.

19. The contact lens of claim 18, wherein said prepolymerization mixture further 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, isobornyl methacrylate, trifluoroethyl methacrylate, hexafluoroisopropyl methacrylate, hexafluorobutyl (meth)acrylate, tri s-trimethyl silyloxy-silyl-propyl methacrylate, 3-methacryloxypropylpentamethyldisiloxane, bis(methacryloxypropyl) tetramethyldisiloxane and combinations thereof.

20. The contact lens of claim 17, wherein said prepolymerization mixture further 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, isobornyl methacrylate, trifluoroethyl methacrylate, hexafluoroisopropyl methacrylate, hexafluorobutyl (meth)acrylate, tri s-trimethyl silyloxy-silyl-propyl methacrylate, 3-methacryloxypropylpentamethyldisiloxane, bis(methacryloxypropyl) tetramethyldisiloxane and combinations thereof.