Hydrophilized carbosiloxane vinylic monomers

• US 9,684,095 B2
• Filed: 04/23/2015
• Issued: 06/20/2017
• Est. Priority Date: 04/25/2014
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Chang, Frank, Huang, Jinyu
• Primary Examiner(s): Yoon, Tae H
• Application Number:
  US14/694,150
• Publication Number:
  US 20150309210A1
• Time in Patent Office: 789 Days
• Field of Search: 523107, 528 32
• CPC Class Codes: C07F 7/1804 Compounds having Si-O-C linkages Si-O-acyl linkages C07F7/1896
• CPC Class Codes: C07F 9/09 Esters of phosphoric acids
• CPC Class Codes: C07F 9/092 substituted by B, Si or a metal
• CPC Class Codes: C08F 230/08 containing silicon
• CPC Class Codes: C08F 283/124 on to polysiloxanes having carbon-to-carbon double bonds
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/38 Polysiloxanes modified by chemical after-treatment C08G77/045 takes precedence
• CPC Class Codes: C08G 77/388 containing nitrogen
• CPC Class Codes: C08G 77/392 containing sulfur
• CPC Class Codes: C08G 77/395 containing phosphorus
• CPC Class Codes: C08G 77/50 by carbon linkages C08G77/485 takes precedence
• CPC Class Codes: C08L 101/14 the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
• CPC Class Codes: C08L 33/10 Homopolymers or copolymers of methacrylic acid esters
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: C08L 83/14 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms C08L83/10 takes precedence
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

The invention provides a hydrophilized carbosiloxane vinylic monomer which comprises (1) a poly(carbosiloxane) segment, (2) one sole ethylenically unsaturated group, and (3) at least one terminal or pendant group which is a hydrophilic group or hydrophilic polymer chain. 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 hydrophilized carbosiloxane vinylic monomer of the invention.

Claims

1. A carbosiloxane vinylic monomer of formula (I)

2. The carbosiloxane vinylic monomer of claim 1, wherein Q is a (meth)acryloyloxy or (meth)acrylamido group.

3. The carbosiloxane vinylic monomer of claim 1, wherein the carbosiloxane vinylic monomer is represented by one of formula (I-1-c)-(I-1-f), (I-2-c)-(I-2-f), (I-3-c)-(I-3-h), (I-4-c)-(I-4-h), and (I-5-c)-(I-5-h)

4. The carbosiloxane vinylic monomer of claim 1, wherein G₁, G₂, G₃, and G₄ are phosphocholine groups.

5. The carbosiloxane vinylic monomer of claim 1, wherein G₁, G₂, G₃, and G₄ are poly(oxazoline) chains.

6. The carbosiloxane vinylic monomer of claim 1, wherein G₁, G₂, G₃, and G₄ are poly(ethyleneglycol) chains.

7. The carbosiloxane vinylic monomer of claim 1, wherein G₁, G₂, G₃, and G₄ independent of one another are selected from the group consisting of a poly(N-vinylpyrrolidone) chain, a poly[N,N-dimethyl (meth)acrylamide] chain, a poly[(meth)acrylamide] chain, a poly(N-vinyl-N-methyl acetamide) chain, a poly(N-vinyl acetamide) chain, a poly(N-vinyl formamide) chain, and a poly(N-methyl-3-methylene-2-pyrrolidone).

8. A carbosiloxane vinylic monomer of any one of formula (I-1-g), (I-1-h), (I-1-i), (I-2-g), and (I-2-h)