Amphiphilic siloxane-containing vinylic monomers and uses thereof

Patent metadata

Field	Value
Publication number	US-9541676-B2
Application number	US-201514793767-A
Country	US
Kind code	B2
Filing date	Jul 8, 2015
Priority date	Dec 14, 2012
Publication date	Jan 10, 2017
Grant date	Jan 10, 2017

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.

First claim

What is claimed is:

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-X 1 - h L-X 2 —BSi  (I)

In which:
Q is an ethylenically unsaturated group of formula (II)

in which
R 12 is hydrogen or C 1 -C 4 alkyl,
Z 1 is a linear or branched C 1 -C 12 alkylene radical, —O—, or —NH—,
Z 2 is a direct bond or a linear or branched C 1 -C 12 alkylene radical,
A is —O— or —NH—,
q 1 and q 2 independent of each other are an integer of 0 or 1;

X 1 and X 2 independent of each other are a direct bond or a cross linkage of formula (III)
—X 3 —R′ 1 —X 4 -E-X 5 —R′ 2 —X 6   (III)

in which
X 3 , X 4 , X 5 , and X 5 independent of one other are a linkage selected from the group consisting of a direct bond, —O—, —NR′—, —CO—NR′—, —NR′—CO—, —NR′—CO—NH—, —NH—CO—NR′—, —O—CO—NH—, —NH—CO—O—, —S—CO—NH—, —O—CO—, —CO—O—, —S—, and —NH—CO—S— in which R′ is H or C 1 -C 4 alkyl,
E is a linear or branched alkylene, cycloalkane diradical or arene diradical with up to 40 carbon atoms,
R′ 1 and R′ 2 independent of each other is a direct bond, a linear or branched C 1 -C 10 alkylene divalent radical, or a divalent radical of —R′ 3 —X 4 -E-X 5 —R′ 4 — in which E, X 4 and X 5 are as defined above and R′ 3 and R′ 4 independent of each other are a direct bond or a linear or branched C 1 -C 10 alkylene radical;

hL is a hydrophilic oligomeric segment selected from the group consisting of (1) polyoxazoline (—[(N(COR″)C 2 H 4 — in which R″ is H, methyl or ethyl) which is obtained in a ring-opening polymerization of oxazoline, (2) a polypeptide segment composed of at least one amino acid selected from the group consisting of asparagine, glutamine, alanine, glycine, and combinations thereof, and (3) a hydrophilic polymer segment composed of hydrophilic monomeric units derived from at least one hydrophilic vinylic monomer selected from the group consisting of (meth)acrylamide, N,N-dimethyl (meth)acrylamide, dimethylaminoethyl (meth)acrylate, dimethylaminoethyl (meth)acrylamide, N-vinyl-2-pyrrolidone, N-vinyl-N-methyl isopropylamide, N-vinyl-N-methyl acetamide, N-vinyl formamide, N-vinyl acetamide, N-vinyl isopropylamide, N-vinyl-N-methyl acetamide, N-methyl-3-methylene-2-pyrrolidone, 1-ethyl-3-methylene-2-pyrrolidone, 1-methyl-5-methylene-2-pyrrolidone, 1-ethyl-5-methylene-2-pyrrolidone, 5-methyl-3-methylene-2-pyrrolidone, 5-ethyl-3-methylene-2-pyrrolidone, 1-n-propyl-3-methylene-2-pyrrolidone, 1-n-propyl-5-methylene-2-pyrrolidone, 1-isopropyl-3-methylene-2-pyrrolidone, 1-isopropyl-5-methylene-2-pyrrolidone, 1-n-butyl-3-methylene-2-pyrrolidone, 1-tert-butyl-3-methylene-2-pyrrolidone, and mixtures thereof;
BSi is a monovalent radical of formula (1A) or (1B)

in which
Y is a C 1 -C 6 alkylene radical or a C 1 -C 6 substituted alkylene radical containing one or more hydroxyl groups,
B 1 and B 2 independent of each other are C 1 -C 6 alkyl, phenyl, or benzyl,
T is a C 1 -C 12 alkyl or an alkoxyalkyl radical having 3 to 8 carbon atoms,
m is an integer of 0 to 3,
p is an integer of 1 to 6,
r is an integer of 2 to 20,
A 1 , A 2 and A 3 independent of each other are C 1 -C 6 alkyl, phenyl, benzyl, or a radical of formula (2)

in which B 3 , B 4 and B 5 independent of each other are C 1 -C 6 alkyl, phenyl, or benzyl, provided that at least two of A 1 , A 2 and A 3 are radicals of formula (2),

(c) at least one hydrophilic vinylic monomer, and
(d) at least one component selected from the group consisting of a hydrophilized polysiloxane-containing crosslinker, a hydrophilic crosslinker, a photoinitiator, a thermal initiator, a UV-absorbing vinylic monomer, a visibility tinting agent, an antimicrobial agent, a bioactive agent, a leachable lubricant, a leachable tear-stabilizing agent, and mixtures thereof; polymerizing the lens-forming formulation in the mold to form a silicone hydrogel contact lens, wherein the formed silicone hydrogel 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 40 barrers, and an elastic modulus of from about 0.1 MPa to about 2.0 MPa.

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.

Assignees

• Novartis Ag

Inventors

• Chang Frank

Classifications

• G02B1/043 Primary

  Contact lenses · CPC title

• C07F7/0838

  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 title

• B29D11/00038

  Production of contact lenses · CPC title

• C07F7/089

  Treatments not covered by a preceding group · CPC title

• C08F30/08

  containing silicon · CPC title