Water-processable silicone-containing prepolymers and uses thereof

• US 9,921,340 B2
• Filed: 10/14/2015
• Issued: 03/20/2018
• Est. Priority Date: 10/06/2010
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Huang, Jinyu, Chang, Frank, Scott, Robert, Medina, Arturo Norberto, Shankar, Venkat, Kuyu, Selma, Smith, Dawn Alison, Wu, Daqing
• Primary Examiner(s): PEPITONE, MICHAEL F
• Application Number:
  US14/883,142
• Publication Number:
  US 20160033683A1
• Time in Patent Office: 888 Days
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/42 Block-or graft-polymers containing polysiloxane sequences polymerising aliphatic unsaturated monomers on to a polysiloxane C08F283/12
• CPC Class Codes: C08G 77/442 containing vinyl polymer sequences
• CPC Class Codes: C08J 2343/04 Homopolymers or copolymers of monomers containing silicon
• CPC Class Codes: C08J 2383/08 containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
• CPC Class Codes: C08J 3/075 Macromolecular gels
• CPC Class Codes: C08L 101/14 the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: C08L 83/10 Block- or graft-copolymers containing polysiloxane sequences obtained by polymerising a compound having a carbon-to-carbon double bond on to a polysiloxane C08L51/08, C08L53/00
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

The invention provide a class of water-processable polymerizable prepolymers which comprises (1) siloxane-containing monomeric units derived at least one siloxane containing monomer having one hydrophilic group or chain and/or polysiloxane-containing crosslinking units derived from at least one hydrophilized polysiloxane or chain-extended polysiloxane crosslinker; (2) hydrophilic monomeric units derived from one or more hydrophilic vinylic monomers; and (3) from about 0.05% to about 5% by weight of polymerizable units each having a pendant or terminal, ethylenically-unsaturated group and free of any polysiloxane segment. The prepolymer comprises from about 20% to about 50% by weight of silicone relative to the total weight of the prepolymer and has a high water solubility or dispersibility of at least about 5% by weight in water and suitable for making silicone hydrogel contact lenses.

Claims

1. A silicone hydrogel contact lens obtained by curing a lens forming formulation including a water-processable prepolymer which comprises:

(1) polysiloxane-containing crosslinking units, wherein the polysiloxane-containing crosslinking units are derived from at least one hydrophilized polysiloxane crosslinker and/or chain-extended hydrophilized polysiloxane crosslinker of formula (7) or (8);

(2) hydrophilic monomeric units derived from one or more hydrophilic vinylic monomers;

(3) from about 0.05% to about 5% by weight of polymerizable units each having a pendant or terminal, ethylenically-unsaturated group and free of any polysiloxane segment; and

(4) optionally hydrophobic units derived from at least one hydrophobic vinylic monomer free of silicone,

2. A method for making silicone hydrogel contact lenses, comprising the steps of:

(1) introducing a lens formulation into a mold for making contact lenses, wherein the lens-forming formulation comprises

(a) a mixture including a hydrophilic vinylic monomer and a polymerizable component selected from the group consisting of a crosslinker of formula (7), a crosslinker of formula (8), and combinations thereof,

3. The method of claim 2, further comprising a step of extracting the formed silicone hydrogel contact lens with water or an aqueous solution.

4. The method of claim 2, wherein the mold is a reusable mold, wherein the lens-forming composition is cured actinically under a spatial limitation of actinic radiation to form the silicone hydrogel contact lens, and wherein the reusable mold is cleaned with an ophthalmically compatible solvent.

5. The method of claim 4, wherein the mold is made of quartz, glass, sapphire, CaF₂, a cyclic olefin copolymer, polymethylmethacrylate (PMMA), polyoxymethylene, polyetherimide, and combinations thereof.