Tris(trimethyl siloxyl)silane vinylic monomers and uses thereof

Patent metadata

Field	Value
Publication number	US-9475827-B2
Application number	US-201314651539-A
Country	US
Kind code	B2
Filing date	Dec 13, 2013
Priority date	Dec 14, 2012
Publication date	Oct 25, 2016
Grant date	Oct 25, 2016

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.

First claim

What is claimed is:

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

in which: q1 is an integer of from 6 to 20; R 1 is hydrogen or methyl; R 2 is a diradical of an alkane or cycloalkane which comprises up to 20 carbon atoms and may have one or more ether, thio, amine, carbonyl, or amido linkages in the main chain.

2. The TRIS-containing vinylic monomer of claim 1 , wherein R 2 is a C 2 -C 5 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.

Assignees

• Novartis Ag
• Shin-Etsu Chemical Company Ltd

Inventors

• Chang Frank
• Hagiwara Mamoru
• Ichinohe Shoji

Classifications

• G02B1/043 Primary

  Contact lenses · CPC title

• C08L101/14

  the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels · CPC title

• C08L33/08

  Homopolymers or copolymers of acrylic acid esters · CPC title

• C08F287/00

  Macromolecular compounds obtained by polymerising monomers on to block polymers · CPC title

• C08L51/085

  on to polysiloxanes · CPC title