Method of making silicone hydrogel contact lenses

• US 7,858,000 B2
• Filed: 06/06/2007
• Issued: 12/28/2010
• Est. Priority Date: 06/08/2006
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Winterton, Lynn Cook
• Primary Examiner(s): Vargot; Mathieu D.
• Application Number:
  US11/810,601
• Publication Number:
  US 20080174035A1
• Time in Patent Office: 1,301 Days
• Field of Search: 264/1.1, 264/1.36, 264/1.38, 264/1.7, 264/2.5, 425/810
• US Class Current: 264/1.38
• CPC Class Codes: B29D 11/00038 Production of contact lenses
• 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: B29D 11/00865 Applying coatings; tinting; colouring printing, marking or copying processes B41M; identification in general G09F3/00; producing decorative effects in general B44C; positioning or marking of lenses B24B13/0055
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

The invention provides a cost-effective method for making a silicone hydrogel contact lens which has a good wettable coating with a good durability.

Claims

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

(a) obtaining a mold having a first mold half and a second mold half, wherein the first mold half includes a first molding surface and the second mold half includes a second molding surface, wherein the first and second mold halves are configured to receive each other such that a lens-forming cavity is formed between the first molding surface and the second molding surface;

(b) applying a first transferable LbL coating to the first molding surface and a second transferable LbL coating to the second molding surface, wherein each of the first and second transferable LbL coatings comprises at least one layer of a first polyionic polymeric material and optionally at least one layer of a second polyionic material or a non-charged hydrophilic polymer with a hydrophobic backbone, wherein the first and second polyionic material each have a hydrophobic backbone and multiple ionizable or charged pendant groups, wherein the first and second polyionic materials have charges opposite to each other;

(c) dispensing a silicone hydrogel lens-forming fluid material into the lens-forming cavity of the mold with the first and second transferable LbL coatings on their molding surfaces, wherein the silicone-hydrogel lens-forming material comprises a non-crosslinkable hydrophilic polymer and at least one member selected from the group consisting of a silicone-containing vinylic monomer, a silicone-containing macromer with ethylenically unsaturated groups, a crosslinkable silicone-containing prepolymer, and mixtures thereof, wherein the non-crosslinkable hydrophilic polymer is capable of forming an interfacial film at an interface between the coated molding surfaces and the lens-forming fluid material;

(d) soaking the transferable LbL coatings with the lens-forming fluid material for a time period sufficient both to allow the non-crosslinkable hydrophilic polymer in the interface film to penetrate into the transferable LbL coatings and to entangle with coating materials in the transferable LbL coatings; and

(e) curing the lens-forming material within the lens-forming cavity to form the silicone hydrogel contact lens, whereby the transferable LbL coatings detach from the molding surfaces and reattach to the formed silicone hydrogel contact lens such that said silicone hydrogel contact lens becomes coated with the transferable LbL coatings,

wherein the non-crosslinkable hydrophilic polymer has a molecular weight or structure that promotes entanglement of the non-crosslinkable hydrophilic polymer in the interfacial film with the polymer matrix of the formed lens so as to obtain a wettable surface coating with a good coating durability characterized by surviving at least five consecutive digital rubbing tests.

2. The method of claim 1, wherein the silicone hydrogel lens-forming fluid material has a temperature of from about 45°

C. to about 95°

C.

3. The method of claim 2, wherein each of the first and second transferable LbL coatings comprises at least one layer of the first polyionic polymeric material and at least one layer of the second polyionic material.

4. The method of claim 2, wherein each of the first and second transferable LbL coatings comprises at least one layer of the first polyionic polymeric material and at least one layer of the non-charged hydrophilic polymer with a hydrophobic backbone, wherein the non-charged hydrophilic polymer is selected from the group consisting of a polyvinyl alcohol, a homopolymer of a vinyl lactam, a copolymer of at least one vinyl lactam with one or more hydrophilic vinylic comonomers, and mixtures thereof.

5. The method of claim 4, wherein the non-charged hydrophilic polymer is a polyvinyl alcohol, polyvinylpyrrolidone, or a mixture thereof.

6. The method of claim 2, wherein the first and second transferable LbL coatings are different from each other.

7. The method of claim 2, wherein the silicone hydrogel lens-forming fluid material comprises from about 1% to about 8.0% by weight of the non-crosslinkable hydrophilic polymer, wherein the non-crosslinkable hydrophilic polymer is selected from the group consisting of a polyvinylalcohol, polyethylene oxide, a polyethylene-polypropylene block copolymers, polyamides, a polyimides, a polylactone, a homopolymer of a vinyl lactam, a copolymer of a vinyl lactam, a homopolymer of acrylamide, a homopolymer of methaacrylamide, a copolymer of acrylamide, a copolymer of methacrylamide with one or more hydrophilic vinylic monomers, and mixtures thereof, wherein the number-average molecular weight M_n of a non-crosslinkable hydrophilic polymer is at least 40000 daltons.

8. The method of claim 2, wherein the silicone hydrogel lens-forming material further comprises silver nanoparticles in an amount sufficient to impart to the resultant silicone hydrogel contact lens an antimicrobial activity characterized by having at least a 5-fold reduction (≧

80% inhibition).

9. The method of claim 1, wherein the silicone hydrogel lens-forming material comprises a crosslinkable silicone-containing prepolymer and is substantially free of vinylic monomer, wherein the crosslinkable silicone-containing prepolymer is substantially purified prior to preparation of the silicone-hydrogel lens-forming fluid material, wherein the step of curing is carried out under a spatial limitation of actinic radiation to form the contact lens.

10. The method of claim 1, wherein each of the first and second transferable LbL coatings comprises at least one layer of the first polyionic polymeric material and at least one layer of the second polyionic material.

11. The method of claim 1, wherein each of the first and second transferable LbL coatings comprises at least one layer of the first polyionic polymeric material and at least one layer of the non-charged hydrophilic polymer with a hydrophobic backbone, wherein the non-charged hydrophilic polymer is selected from the group consisting of a polyvinyl alcohol, a homopolymer of a vinyl lactam, a copolymer of at least one vinyl lactam with one or more hydrophilic vinylic comonomers, and mixtures thereof.

12. The method of claim 11, wherein the non-charged hydrophilic polymer is a polyvinyl alcohol, polyvinylpyrrolidone, or a mixture thereof.

13. The method of claim 1, wherein the first and second transferable LbL coatings are different from each other.

14. The method of claim 1, wherein the silicone hydrogel lens-forming fluid material comprises from about 1% to about 8.0% by weight of the non-crosslinkable hydrophilic polymer, wherein the non-crosslinkable hydrophilic polymer is selected from the group consisting of a polyvinylalcohol, polyethylene oxide, a polyethylene-polypropylene block copolymers, polyamides, a polyimides, a polylactone, a homopolymer of a vinyl lactam, a copolymer of a vinyl lactam, a homopolymer of acrylamide, a homopolymer of methaacrylamide, a copolymer of acrylamide, a copolymer of methacrylamide with one or more hydrophilic vinylic monomers, and mixtures thereof, wherein the number-average molecular weight M_n of a non-crosslinkable hydrophilic polymer is at least 40000 daltons.

15. The method of claim 1, wherein the silicone hydrogel lens-forming material further comprises silver nanoparticles in an amount sufficient to impart to the resultant silicone hydrogel contact lens an antimicrobial activity characterized by having at least a 5-fold reduction (≧

80% inhibition).

16. The method of claim 9, wherein the silicone hydrogel lens-forming fluid material has a temperature of from about 45°

C. to about 95°

C.

17. The method of claim 16, wherein each of the first and second transferable LbL coatings comprises at least one layer of the first polyionic polymeric material and at least one layer of the second polyionic material.

18. The method of claim 16, wherein each of the first and second transferable LbL coatings comprises at least one layer of the first polyionic polymeric material and at least one layer of the non-charged hydrophilic polymer with a hydrophobic backbone, wherein the non-charged hydrophilic polymer is selected from the group consisting of a polyvinyl alcohol, a homopolymer of a vinyl lactam, a copolymer of at least one vinyl lactam with one or more hydrophilic vinylic comonomers, and mixtures thereof.

19. The method of claim 18, wherein the non-charged hydrophilic polymer is a polyvinyl alcohol, polyvinylpyrrolidone, or a mixture thereof.

20. The method of claim 16, wherein the first and second transferable LbL coatings are different from each other.