Macroinitiator containing hydrophobic segment

Patent metadata

Field	Value
Publication number	US-2016194497-A1
Application number	US-201615071752-A
Country	US
Kind code	A1
Filing date	Mar 16, 2016
Priority date	May 4, 2011
Publication date	Jul 7, 2016
Grant date	—

Abstract

The present invention relates to macroinitiators comprising at least one hydrophobic segments in a molecule, wherein a molecular weight of the hydrophobic segment is 300 to 1800. The present invention further relates to block copolymers, wetting agent and polymeric materials having the block copolymers of the present invention associated with, which is suitable for medical devices, particularly for ophthalmic devices, including contact lenses, ophthalmic lenses, punctal plugs and artificial corneas.

First claim

1 - 13 . (canceled)

14 . The medical device according to claim 19 , wherein a weight-average molecular weight of the block copolymer is from approximately 10,000 to approximately 3,000,000.

15 . The medical device according to claim 19 , wherein the block copolymer contains approximately 0.01 to approximately 5 weight % of a hydrophobic segment and approximately 95 to approximately 99.9 weight % of a hydrophilic segment.

16 - 18 . (canceled)

19 . A medical device comprising a silicone hydrogel and a block copolymer expressed by formula (b1) or (b2):

wherein in (b1), R 1 is selected from the group consisting of an alkyl group or an alkoxy group;
R 2 is selected from the group consisting (CH 2 ) n and (CH 2 ) m —O(CH 2 ) n ;
m and n are independent, ranging from 1 to 16; a is from 4 to 19; b is from 1 to 6, c is from 1 to 10,000, X is selected from the group consisting O, NH, and S; and R 3 and R 4 represent hydrophilic groups from hydrophilic monomers expressed by general formula (n)

20 . The medical device according to claim 19 , comprising approximately 0.1 ppm to approximately 30% of the block copolymer.

21 . The medical device according to any one of claims 19 through 20 , wherein the silicone hydrogel is formed from a reactive mixture comprising at least one hydrophilic monomer selected from the group consisting of N,N-dimethyl acrylamide (DMA), 2-hydroxyethyl acrylate, glycerol methacrylate, 2-hydroxyethyl methacrylate amide, polyethylene glycol mono methacrylate, methacrylic acid, acrylic acid, N-vinyl pyrrolidone, N-vinyl-N-methyl acetamide, N-vinyl-N-ethyl acetamide, N-vinyl-N-ethyl form amide, N-vinyl formamide, N-2-hydroxyethyl vinyl carbamate, N-carboxy-beta-alanine N-vinylester, reactive polyethylene polyol, hydrophilic vinyl carbonate, vinyl carbamate monomer, hydrophilic oxazolone monomer, hydrophilic oxazoline monomer, and combinations thereof.

22 . The medical device according to any one of claims 19 through 21 , wherein the silicone hydrogel is formed from a reactive mixture comprising at least one silicone monomer comprising at least one hydroxyl group.

23 . The medical device according to claim 22 , wherein said reactive mixture comprises approximately 5 to approximately 95 weight % silicone containing components.

24 . The medical device according to claim 19 wherein said medical device is an ophthalmic device.

25 . The ophthalmic device according to claim 24 wherein said ophthalmic device is a contact lens.

26 . The medical device of claim 19 wherein the block copolymer is a copolymer of Formula (b1).

27 . The medical device of claim 19 or 24 - 26 wherein said hydrophilic monomer of Formula n is selected from the group consisting of vinyl amides, vinylimides, vinyl lactams, hydrophilic (meth)acrylates, (meth)acrylamides, styrenics, vinyl ethers, vinyl carbonates, vinyl carbamates, vinyl ureas and mixtures thereof.

28 . The medical device of claim 19 or 24 - 26 wherein said hydrophilic monomer reacted to form said block copolymer is selected from the group consisting of N-vinyl pyrrolidone, N-vinyl-2-piperidone, N-vinyl-2-caprolactam, N-vinyl-3-methyl-2-caprolactam, N-vinyl-3-methyl-2-piperidone, N-vinyl-4-methyl-2-piperidone, N-vinyl-4-methyl-2-caprolactam, N-vinyl-3-ethyl-2-pyrrolidone, N-vinyl-4,5-dimethyl-2-pyrrolidone, vinylimidazole, N—N-dimethylacrylamide, acrylamide, N,N-bis(2-hydroxyethyl)acrylamide, acrylonitrile, N-isopropyl acrylamide, vinyl acetate, (meth)acrylic acid, polyethylene glycol (meth)acrylates, 2-ethyl oxazoline, N-(2-hydroxypropyl) (meth)acrylamide, N-(2-hydroxyethyl) (meth)acrylamide, 2-methacryloyloxyethyl phosphorylcholine, 3-(dimethyl(4-vinylbenzyl)ammonio)propane-1-sulfonate (DMVBAPS), 3-((3-acrylamidopropyl)dimethylammonio)propane-1-sulfonate (AMPDAPS), 3-((3-methacrylamidopropyl)dimethylammonio)propane-1-sulfonate (MAMPDAPS), 3-((3-(acryloyloxy)propyl)dimethylammonio)propane-1-sulfonate (APDAPS), 3-((3-methacryloyloxy)propyl)dimethylammonio)propane-1-sulfonate (MAPDAPS), N-vinyl-N-methylacetamide, N-vinylacetamide, N-vinyl-N-methylpropionamide, N-vinyl-N-methyl-2-methylpropionamide, N-vinyl-2-methylpropionamide, N-vinyl-N,N′-dimethylurea, and mixtures thereof.

29 . The medical device of claim 19 or 24 - 26 wherein said hydrophilic monomer comprises at least one monomer selected from the group consisting of N-vinyl pyrrolidone, N-vinyl-N-methylacetamide, 2-methacryloyloxyethyl phosphorylcholine, (meth)acrylic acid, N,N dimethylacrylamide and mixtures thereof.

30 . The medical device of claim 19 or 24 - 26 wherein R 1 is methyl or butyl.

Assignees

• Johnson & Johnson Vision Care

Inventors

• Tamiya Ryuta
• Fujisawa Kazuhiko
• Nakamura Masataka

Classifications

• G02B1/043

  Contact lenses · CPC title

• C08L2201/10

  Transparent films; Clear coatings; Transparent materials · CPC title

• C08L83/10 Primary

  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 title

• C08L2201/54

  Aqueous solutions or dispersions · CPC title

• C08L2203/02

  for biomedical use · CPC title