Extended wear ophthalmic lens

Patent metadata

Field	Value
Publication number	US-9612455-B2
Application number	US-201314033986-A
Country	US
Kind code	B2
Filing date	Sep 23, 2013
Priority date	Apr 4, 1995
Publication date	Apr 4, 2017
Grant date	Apr 4, 2017

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.

First claim

What is claimed is:

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 −6 cm 2 /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 −6 cm 2 /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 comb

Assignees

• Ciba Vision Corp
• Novartis 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 Jr Wilson Leonard
• Vogt Jurgen
• Winterton Lynn Cook

Classifications

• B29L2011/0041

  Contact lenses · CPC title

• C08G18/63

  Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers · CPC title

• B05D1/62

  Plasma-deposition of organic layers (plasma deposition in general C23C14/00, C23C16/00) · CPC title

• B29D11/00076

  enabling passage of fluids, e.g. oxygen, tears, between the area under the lens and the lens exterior · CPC title

• A61L2430/16

  for reconstruction of eye parts, e.g. intraocular lens, cornea · CPC title