Contact lenses with a lubricious coating thereon

Patent metadata

Field	Value
Publication number	US-10962803-B2
Application number	US-201916260544-A
Country	US
Kind code	B2
Filing date	Jan 29, 2019
Priority date	Jan 30, 2018
Publication date	Mar 30, 2021
Grant date	Mar 30, 2021

Abstract

The invention is generally related to a soft contact lens which comprises a hydrogel lens body and a coating of a hydrophilic copolymer thereon and to a method for producing the same. The hydrogel lens body comprises or is made of a polymeric material having 1,2- and/or 1,3-diol moieties, and the hydrophilic copolymer comprises arylborono-containing repeating units each having a boronic acid group. The coating is covalently-attached to the hydrogel lens body through cyclic boronic ester linkages each formed between one boronic acid group and one 1,2-diol or 1,3-diol group. The soft contact lens has a surface lubricity higher than the surface lubricity of the lens body.

First claim

What is claimed is:

1. A soft contact lens, comprising:
a hydrogel lens body and a coating thereon, wherein the hydrogel lens body comprises or is made of a polymeric material having 1,2- and/or 1,3-diol moieties,

wherein the coating comprises a layer of a hydrophilic copolymer comprising (a) arylborono-containing repeating units each having a boronic acid group and (b) repeating units of at least one hydrophilic vinylic monomer, wherein said at least one hydrophilic vinylic monomer comprises a phosphorylcholine-containing vinylic monomer,
wherein the coating is covalent attached onto the hydrogel lens body through linkages each formed between one of the boronic acid groups of the hydrophilic copolymer and one of the 1,2-diol and 1,3-diol moieties of the polymeric material.

2. The soft contact lens of claim 1 , wherein the soft contact lens has a friction rating of about 2.5 or lower.

3. The soft contact lens of claim 2 , wherein the soft contact lens has an equilibrium water content of from about 15% to about 80% by weight at a temperature of from about 22° C. to 28° C., and/or an elastic modulus of from about 0.2 MPa to about 1.5 MPa when being fully hydrated.

4. The soft contact lens of claim 3 , wherein the hydrogel lens body comprises or is made of a polymeric material comprising at least 50% by mole of repeating units of vinyl alcohol.

5. The soft contact lens of claim 4 , wherein the hydrogel lens body comprises or is made of a polymeric material which is a polymerization product of a water-soluble, actinically-crosslinkable polyvinylalcohol prepolymer which comprises: repeating units of vinyl alcohol and repeating units of formula (I)

in which:
R 3 is hydrogen or a C 1 -C 6 alkyl group;
R 4 is a C 1 -C 6 alkylene divalent radical;
R 5 is hydrogen or C 1 -C 6 alkyl;
R 6 is an ethylenically unsaturated group of

in which q1 and q2 independently of each another are zero or one, and R 7 and R 8 independently of one another are a C 2 -C 8 alkylene divalent radical, R 9 is C 2 -C 8 alkenyl.

6. The soft contact lens of claim 5 , wherein the polyvinylalcohol prepolymer has a weight average molecular weight of at least about 2,000 Daltons, and comprises from about 1% to about 25% by mole of the repeating units of formula (I).

7. The soft contact lens of claim 5 , wherein the arylborono-containing repeating units is derived from at least one arylborono-containing vinylic monomer of formula (II)

in which:
R 1 is H, NO 2 , F, Cl, or CF 3 ; Q is a monovalent radical of

or —CH═CH 2 ; L is a direct bond, a C 1 -C 4 alkylene divalent radical, a divalent radical of

in which Y 1 is CH(OH) or a C 1 -C 4 alkylene divalent radical, Y 2 is a C 1 -C 4 alkylene divalent radical, and R o is H or a C 1 -C 4 alkyl.

8. The soft contact lens of claim 5 , wherein the arylborono-containing repeating units is derived from at least one arylborono-containing vinylic monomer selected from the group consisting of 3-vinylphenylboronic acid, 4-vinylboronic acid, 3-(meth)acrylamidophenylboronic acid, 4-(meth)acrylamidophenylboronic acid, and combinations thereof.

9. The soft contact lens of claim 5 , wherein the arylborono-containing repeating units is derived from at least one arylborono-containing vinylic monomer selected from the group consisting of a reaction production of an amino-containing phenylboronic acid derivative with (meth)acrylic acid halide, a reaction product of an amino-containing phenylboronic acid derivative with a carboxy-containing vinylic monomer in the presence of a carbodiimide and N-hydroxysuccinimide, a reaction production of a carboxy-containing phenylboronic acid derivative with an amino-containing vinylic monomer in the presence of a carbodiimide and N-hydroxysuccinimide, and combinations thereof, wherein the carboxy-containing phenylboronic acid derivative is selected from the group consisting of 3-carboxyphenylboronic acid, 4-carboxyphenylboronic acid, 3-boronophenylacetic acid, 4-boronophenylacetic acid, 2-(4-boronophenyl)-2-methylpropanoic acid, 3-(4-boronophenyl)propanoic acid, 3-(3-boronophenyl)propanoic acid, 5-(3-boronophenyl)pentanoic acid, 5-(4-boronophenyl)pentanoic acid, 4-(2-carboxyethyl)-3-nitrophenylboronic acid, 3-(3-carboxypropyonylamino)phenylboronic acid, 3-amino-3-(4-boronophenyl)propanoic acid, and combinations thereof, wherein the amino-containing phenylboronic acid derivative is selected from the group consisting of 3-aminophenylboronic acid, 4-aminophenylboronic acid, 4-amino-3-nitrophenylboronic acid, 4-amino-4-fluorophenylboronic acid, 2-(aminomethyl)-5-nitrophenylboronic acid, 3-(aminomethyl)-phenylboronic acid, 3-amino-5-nitrophenylboronic acid, 3-amino-3-(4-boronophenyl)propanoic acid, and combinations thereof,
wherein the carboxy-containing vinylic monomer is selected from the group consisting of 2-acrylamidoglycolic acid, 3-acrylamidopropionic acid, 4-acrylamidobutanoic acid, 5-acrylamidopentanoic acid, 3-acryloyloxypropanoic acid, 4-acryloyloxybutanoic acid, 5-acryloyloxypentanoic acid, and combinations thereof,
wherein the amino-containing vinylic monomers is selected from the group consisting of amino-C 2 -C 4 alkyl (meth)acrylate, C 1 -C 3 alkylamino-C 2 -C 4 alkyl (meth)acrylate, amino-C 2 -C 4 alkyl (meth)acrylamide, C 1 -C 3 alkylamino-C 2 -C 4 alkyl (meth)acrylamide, vinylamine, allylamine, and combinations thereof.

10. The soft contact lens of claim 5 , wherein said at least one hydrophilic vinylic monomer further comprises at least one vinylic monomer selected from the group consisting of (meth)acrylamide, N,N-dimethyl (meth)acrylamide, N-ethyl (meth)acrylamide, N,N-diethyl (meth)acrylamide, N-propyl (meth)acrylamide, N-isopropyl (meth)acrylamide, N-3-methoxypropyl (meth)acrylamide, N-2-hydroxylethyl (meth)acrylamide, N,N-bis(hydroxyethyl) (meth)acrylamide, N-3-hydroxypropyl (meth)acrylamide, N-2-hydroxypropyl (meth)acrylamide, 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, di(ethylene glycol) (meth)acrylate, tri(ethylene glycol) (meth)acrylate, tetra(ethylene glycol) (meth)acrylate, poly(ethylene glycol) (meth)acrylate having a number average molecular weight of up to 1500, poly(ethylene glycol)ethyl (meth)acrylamide having a number average molecular weight of up to 1500, N-2-aminoethyl (meth)acrylamide, N-2-methylaminoethyl (meth)acrylamide, N-2-ethylaminoethyl (meth)acrylamide, N-2-dimethylaminoethyl (meth)acrylamide, N-3-aminopropyl (meth)acrylamide, N-3-methylaminopropyl (meth)acrylamide, N-3-dimethylaminopropyl (meth)acrylamide, 2-aminoethyl (meth)acrylate, 2-methylaminoethyl (meth)acrylate, 2-ethylaminoethyl (meth)acrylate, 3-aminopropyl (meth)acrylate, 3-methylaminopropyl (meth)acrylate, 3-ethylaminopropyl (meth)acrylate, 3-amino-2-hydroxypropyl (meth)acrylate, trimethylammonium 2-hydroxy propyl (meth)acrylate hydrochloride, dimethylaminoethyl (meth)acrylate, 2-(meth)acrylamidoglycolic acid, (meth)acrylic acid, ethylacrylic acid, propylacrylic acid, 3-(meth)acrylamidopropionic acid, 4-(meth)acrylamidobutanoic acid, 5-(meth)acrylamidopentanoic acid, 3-(meth)acryloyloxypropanoic acid, 4-(meth)acryloyloxybutanoic acid, 5-(meth)acryloyloxypentanoic a

Assignees

• Novartis Ag
• Alcon Inc

Inventors

• Zhang Steve Yun
• Wu Daqing
• Breitkopf Richard Charles
• Lang Weihong
• Ge Junhao
• Gubitosi Raspino Maria F
• Chang Frank
• Moy Thomas M
• Holland Troy Vernon

Classifications

• C08J7/056

  Forming hydrophilic coatings · CPC title

• C09D143/00

  Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Coating compositions based on derivatives of such polymers · CPC title

• G02B1/043

  Contact lenses · CPC title

• C08F230/00

  Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal · CPC title

• G02C7/049 Primary

  Contact lenses having special fitting or structural features achieved by special materials or material structures · CPC title