Amphiphilic siloxane-containing vinylic monomers and uses thereof

• US 9,541,676 B2
• Filed: 07/08/2015
• Issued: 01/10/2017
• Est. Priority Date: 12/14/2012
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Chang, Frank
• Primary Examiner(s): Yoon, Tae H
• Application Number:
  US14/793,767
• Publication Number:
  US 20150309213A1
• Time in Patent Office: 552 Days
• Field of Search: 523/107, 525/479, 351/159.02
• US Class Current: 1/1
• CPC Class Codes: B29D 11/00038 Production of contact lenses
• CPC Class Codes: C07F 7/0838 Compounds with one or more Si-O-Si sequences compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21
• CPC Class Codes: C07F 7/089 Treatments not covered by a preceding group
• CPC Class Codes: C08F 30/08 containing silicon
• CPC Class Codes: C08L 101/14 the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
• CPC Class Codes: C08L 33/26 Homopolymers or copolymers of acrylamide or methacrylamide
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

The invention provides an amphiphilic siloxane-containing vinylic monomer which comprises one sole ethylenically unsaturated group and a siloxane-containing group covalently linked to the ethylenically-unsaturated group through a hydrophilic linker. The present invention is also related to a polymer, an actinically-crosslinkable silicone-containing prepolymer, a silicone hydrogel polymeric material, or a silicone hydrogel contact lens, which comprises monomeric units derived from an amphiphilic siloxane-containing vinylic monomer of the invention. In addition, the invention provides a method for making silicone hydrogel contact lenses using a water-based lens-forming formulation comprising an amphiphilic siloxane-containing vinylic monomer of the invention and/or an actinically-crosslinkable silicone-containing prepolymer of the invention.

Claims

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

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

(a) a solvent selected from the group consisting of water, 1,2-propylene glycol, dipropylene glycol, tripropylene glycol, propylene glycol methyl ether, dipropylene glycol methyl ether, tripropylene glycol methyl ether, a polyethyleneglycol having a molecular weight of about 400 Daltons or less, and mixtures thereof,

(b) at least one amphiphilic siloxane-containing vinylic monomer of formula (I)

Q-X₁-hL-X₂—

BSi 

 

(I)

In which;

Q is an ethylenically unsaturated group of formula (II)

2. The method of claim 1, further comprising the step of extracting the molded silicone hydrogel contact lens with water or an aqueous solution.

3. The method of claim 2, wherein the mold is a reusable mold and the lens-forming composition is cured actinically under a spatial limitation of actinic radiation to form the silicone hydrogel contact lens.