Extended wear ophthalmic lens

• US 8,415,404 B2
• Filed: 06/04/2010
• Issued: 04/09/2013
• Est. Priority Date: 09/06/1994
• Status: Expired due to Fees

• Current Assignee: Novartis Ag
• Original Assignee: CIBA Vision Corporation (Novartis Ag)
• Inventors: Nicolson, Paul Clement, Baron, Richard Carlton, Chabrecek, Peter, Court, John, Domschke, Angelika, Griesser, Hans Jorg, 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): CAIN, EDWARD J
• Application Number:
  US12/794,333
• Publication Number:
  US 20100238398A1
• Time in Patent Office: 1,040 Days
• Field of Search: 523/106
• US Class Current: 523/106
• 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. In one embodiment, an ophthalmic lens is a copolymerization product of at least one oxyperm, at least one ionoperm, and a crosslinker. In one embodiment, a lens has a tensile modulus of less than about 3.0 MPa, yet in another embodiment, the tensile modulus is between about 0.5 to about 1.5 MPa.

Claims

1. A contact lens, comprising:

a core polymeric material formed from polymerization of a prepolymerization mixture including;

(i) one or more oxyperm macromers or monomers selected from the group consisting of siloxane-containing macromers and monomers, fluorine-containing macromers and monomers, carbon-carbon triple bond-containing macromers and monomers, and combinations thereof;

(ii) an ionoperm polymerizable material including at least one hydrophilic monomer;

(iii) less than 5% by weight of a cross-linking agent other than component (i); and

(iv) a solvent,

wherein the contact lens has a diameter of 13 to 15 mm and a center thickness of 40 to 150 microns, and wherein the one or more oxyperm macromers or monomers and the ionoperm polymerizable material are present in the prepolymerization mixture in an amount sufficient to provide the contact lens an oxygen transmissibility of at least 70 barrers/mm, an ion permeability characterized by an Ionoflux Ion Permeability Coefficient of greater than 6.4×

10<sup>−

6</sup> mm²/min, and a tensile modulus of 0.5 to 1.5 MPa, and to provide the contact lens with an ability to be worn for a continuous period of at least 24 hours including a normal sleep period and during which the lens exhibits on-eye movement with blinking and produces less than 8% corneal swelling after the continuous period of wear.

2. The contact lens of claim 1, wherein said one or more oxyperm macromers or monomers are siloxane-containing macromers or monomers.

3. The contact lens of claim 2, wherein the siloxane-containing macromers or monomers contain one or more hydrophilic groups.

4. The contact lens of claim 3, wherein the hydrophilic groups are selected from the group consisting of:

polyoxyethylene, urethane, urea, amide, amine, hydroxyl and combinations thereof.

5. The contact lens of claim 4, wherein said at least one hydrophilic monomer is selected from the group consisting of hydroxyl-substituted lower alkyl acrylate and methacrylate, acrylamide, methacrylamide, (lower alkyl)-acrylamide and -methacrylamide, ethoxylated acrylate and methacrylate, hydroxyl-substituted (lower alkyl)-acrylamide and -methacrylamide, hydroxyl-substituted lower alkyl vinyl ether, sodium vinylsulfonate, sodium styrenesulfonate, 2-acrylamido-2-methylpropanesulfonic acid, N-vinylpyrrole, N-vinyl-2-pyrrolidone, 2-vinyloxazoline, 2-vinyl-4,4′

-dialkyloxazolin-5-one, 2- and 4-vinylpyridine, vinylically unsaturated carboxylic acids having a total of 3 to 5 carbon atoms, amino(lower alkyl)-acrylate and methacrylate, mono(lower alkylamino)(lower alkyl)-acrylate and methacrylate, di(lower alkylamino)(lower alkyl)-acrylate and methacrylate, allyl alcohol, and combinations thereof.

6. The contact lens of claim 3, wherein said at least one hydrophilic monomer is hydroxyethyl methacrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, trimethylammonium 2-hydroxy propylmethacrylate hydrochloride, dimethylaminoethyl methacrylate, dimethylaminoethylmethacrylamide, acrylamide, methacrylamide, N,N-dimethylacrylamide, allyl alcohol, vinylpyridine, glycerol methacrylate, N-(1,1-dimethyl-3-oxobutyl)acrylamide, N-vinyl-2-pyrrolidone, acrylic acid, or methacrylic acid.

7. The contact lens of claim 6, wherein said at least one hydrophilic monomer is hydroxyethyl methacrylate, N,N-dimethylacrylamide, or N-vinyl-2-pyrrolidone.

8. The contact lens of claim 6, wherein the cross-linking agent is selected from the group consisting of allyl(meth)acrylate, C₁-C₆ alkylene glycol di(meth)acrylate, poly C₁-C₆ alkylene glycol di(meth)acrylate, C₁-C₆ 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, diallyl phthalate and combinations thereof.

9. The contact lens of claim 8, wherein the cross-linking agent is present in the prepolymerization mixture in an amount of less than 2% by weight.

10. The contact lens of claim 6, 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, isobornyl methacrylate, trifluoroethyl methacrylate, hexafluoroisopropyl methacrylate, hexafluorobutyl(meth)acrylate, tris-trimethylsilyloxy-silyl-propyl methacrylate (TRIS), 3-methacryloxypropylpentamethyldisiloxane, bis(methacryloxypropyl) tetramethyldisiloxane and combinations thereof.

11. The contact lens of claim 10, wherein the hydrophobic monomer is tris-trimethylsilyloxy-silyl-propyl methacrylate (TRIS).

12. The contact lens of claim 6, wherein the contact lens includes a surface that is more hydrophilic than the core polymeric material of the contact lens.

13. The contact lens of claim 12, wherein one or more surface properties of the contact lens are altered by a surface treatment process.

14. The contact lens of claim 13, wherein the surface treatment process is performed prior to and/or posterior to complete polymerization of the prepolymerization mixture.

15. The contact lens of claim 12, wherein the contact lens has an ability to be worn for a continuous period of wear of at least 24 hours including a normal sleep period during which the lens exhibits on-eye movement with blinking and produces less than 6% corneal swelling after the continuous period of wear.

16. The contact lens of claim 15, wherein the contact lens has an ability to be worn for a continuous period of wear of at least 24 hours including a normal sleep period during which the lens exhibits on-eye movement with blinking and produces less than 4% corneal swelling after the continuous period of wear.