Tris(trimethyl siloxyl)silane vinylic monomers and uses thereof

• US 9,475,827 B2
• Filed: 12/13/2013
• Issued: 10/25/2016
• Est. Priority Date: 12/14/2012
• Status: Active Grant

• Current Assignee: Alcon Incorporated, Shin-Etsu Chemical Company Limited
• Original Assignee: Novartis Ag, Shin-Etsu Chemical Company Limited
• Inventors: Chang, Frank, Hagiwara, Mamoru, Ichinohe, Shoji
• Primary Examiner(s): Salamon, Peter A
• Application Number:
  US14/651,539
• Publication Number:
  US 20150315213A1
• Time in Patent Office: 1,047 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: C07F 7/0834 Compounds having one or more O-Si linkage for compounds with C-O-Si linkages see C07F7/18
• 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 7/0889 Reactions not involving the Si atom of the Si-O-Si sequence
• CPC Class Codes: C08F 287/00 Macromolecular compounds obtained by polymerising monomers on to block polymers
• CPC Class Codes: C08L 101/14 the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
• CPC Class Codes: C08L 33/08 Homopolymers or copolymers of acrylic acid esters
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

The invention provides a TRIS-containing vinylic monomer which comprises one sole (meth)acryloyloxy group and a tris(trimethylsiloxy)silyl group covalently linked to the ethylenically-unsaturated group through a polyoxyethylene 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 a TRIS-containing vinylic monomer of the invention. In addition, the invention provides a method for making a TRIS-containing vinylic monomer of the invention.

Claims

1. A TRIS-containing vinylic monomer, being represented by formula (I)

2. The TRIS-containing vinylic monomer of claim 1, wherein R₂ is a C₂-C₅ alkane diradical.

3. The TRIS-containing vinylic monomer of claim 1, wherein the TRIS-containing vinylic monomer has a water solubility or dispersibility of at least about 5% by weight in water.

4. An actinically-crosslinkable silicone-containing prepolymer having a water solubility or dispersibility of at least about 5% by weight in water and comprising monomeric units derived from a TRIS-containing vinylic monomer of claim 1.

5. The prepolymer of claim 4, which further comprises:

(1) crosslinking units derived from at least one polysiloxane-containing crosslinker and/or polysiloxane units derived from a polysiloxane-containing vinylic monomer;

(2) hydrophilic units derived from at least one hydrophilic vinylic monomer;

(3) polymerizable units derived from a chain transfer agent having a first reactive functional group other than thiol group and/or a vinylic monomer having a second reactive functional group other than ethylenically-unsaturated group, wherein the polymerizable units each comprise an ethylenically unsaturated group covalently attached to one polymerizable unit through the first or second reactive functional group;

(4) optionally non-silicone crosslinking units derived from at least one non-silicone crosslinker; and

(5) optionally UV-absorbing units derived from a UV-absorbing vinylic monomer.

6. A silicone-hydrogel material comprising hydrophilic monomeric units derived from a hydrophilic vinylic monomer and monomeric units derived from a TRIS-containing vinylic monomer of claim 1.

7. A soft contact lens comprising a silicone hydrogel material of claim 6, wherein the soft contact lens has a water content of from about 20% to about 75% by weight when fully hydrated, an oxygen permeability (Dk) of at least about 40 barrers, and an elastic modulus of from about 0.1 MPa to about 2.0 MPa.