Hydrophilic copolymer with one thiol-containing terminal group

Patent metadata

Field	Value
Publication number	US-10287370-B2
Application number	US-201715730780-A
Country	US
Kind code	B2
Filing date	Oct 12, 2017
Priority date	Oct 19, 2016
Publication date	May 14, 2019
Grant date	May 14, 2019

Abstract

The invention is related to a class of hydrophilic polymers each comprising one sole thiol-containing terminal group. The hydrophilic polymers are highly reactive towards azetidinium groups of an azetidinium-containing polymer upon heating and can find particular use in for producing water-soluble highly-branched hydrophilic polymeric material useful for producing water gradient contact lenses.

First claim

What is claimed is:

1. A hydrophilic polymer, comprising:
(1) one sole thiol-containing terminal group of

in which R′ is hydrogen or a C 1 -C 6 alkyl group, R a is hydrogen or methyl, and R b is hydrogen, C 1 -C 3 alkyl, acetyl, or C 2 -C 4 alkanoylamino which optionally has a carboxyl group; and
(2) at least about 75% by mole of repeating units of at least one non-reactive vinylic monomer, wherein said at least one non-reactive vinylic monomer is selected from the group consisting of a phosphorylcholine-containing vinylic monomer, (meth)acrylamide, N,N-dimethyl (meth)acrylamide, N-vinylpyrrolidone (NVP), N-vinyl formamide, N-vinyl acetamide, N-vinyl isopropylamide, N-vinyl-N-methyl acetamide, N,N-dimethylaminoethyl (meth)acrylate, N,N-dimethylaminopropyl (meth)acrylamide, glycerol (meth)acrylate, 3-(meth)acryloylamino-1-propanol, N-hydroxyethyl (meth)acrylamide, N-hydroxypropyl (meth)acrylamide, N-[tris(hydroxymethyl)methyl]-acrylamide, 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, 2-hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, C 1 -C 4 -alkoxy polyethylene glycol (meth)acrylate having a weight average molecular weight of up to 1500 Daltons, allyl alcohol, vinyl alcohol, and combinations thereof.

2. The hydrophilic polymer of claim 1 , wherein R a is hydrogen and R b is acetylamino, propionylamino or butyrylamino.

3. The hydrophilic polymer of claim 1 , wherein R a is hydrogen and R b is acetylamino or propionylamino.

4. The hydrophilic polymer of claim 1 , wherein R a is hydrogen and R b is acetylamino.

5. The hydrophilic polymer of claim 1 , wherein said one or more non-reactive hydrophilic vinylic monomer comprises a phosphorylcholine-containing vinylic monomer.

6. The hydrophilic polymer of claim 1 , wherein said one or more non-reactive hydrophilic vinylic monomers comprises one member selected from the group consisting of (meth)acryamide, N,N-dimethyl (meth)acrylamide, N-vinylpyrrolidone, N-vinyl-N-methyl acetamide, glycerol (meth)acrylate, hydroxyethyl (meth)acrylate, N-hydroxyethyl (meth)acrylamide, N-hydroxypropyl (meth)acrylamide, C 1 -C 4 -alkoxy polyethylene glycol (meth)acrylate having a weight average molecular weight of up to 400 Daltons, N-methyl-3-methylene-2-pyrrolidone, 1-methyl-5-methylene-2-pyrrolidone, 5-methyl-3-methylene-2-pyrrolidone, N,N-dimethylaminoethyl (meth)acrylate, N,N-dimethylaminopropyl (metha)crylamide, and combinations thereof.

7. The hydrophilic polymer of claim 1 , wherein the hydrophilic polymer comprises at least about 85% by mole of repeating units of said one or more non-reactive vinylic monomers.

8. A water-soluble thermally-crosslinkable polymeric material, comprising:
(a) one or more first polymer chain of an azetidinium-containing polymer having azetidinium groups;
(b) second polymer chains of a hydrophilic polymer of claim 1 , wherein each second polymer chain is covalently attached to one of said one or more first polymer chains via one sole linkage of

in which R′, R a and R b are as defined in any one of inventions 1 to 4; and
(c) azetidinium groups each of which is embedded in or covalently attached to one of said one or more first polymer chains.

9. The water-soluble thermally-crosslinkable polymeric material of claim 8 , wherein the azetidinium-containing polymer is polyamidoamine-epichlorohydrin (PAE).

10. The water-soluble thermally-crosslinkable polymeric material of claim 8 , wherein the azetidinium-containing polymer is a poly(2-oxazoline-co-ethyleneimine)-epichlorohydrin.

11. The water-soluble thermally-crosslinkable polymeric material of claim 8 , wherein the azetidinium-containing polymer is a homopolymer of an azetidinium-containing vinylic monomer.

12. The water-soluble thermally-crosslinkable polymeric material of claim 8 , wherein the azetidinium-containing polymer is a copolymer of an azetidinium-containing vinylic monomer with one or more hydrophilic vinylic monomers.

13. The water-soluble thermally-crosslinkable polymeric material of claim 8 , wherein the water-soluble thermally-crosslinkable polymeric material comprises (i) from about 20% to about 95% by weight of the first polymer chains and (ii) from about 5% to about 80% by weight of the second polymer chains.

14. A packaging solution, which is an aqueous solution comprising at least one buffering agent for maintaining a pH of from about 6.0 to about 8.5 and from about 0.01% to about 2% by weight of a water-soluble and thermally-crosslinkable hydrophilic polymeric material of claim 8 , wherein the packaging solution has a tonicity of from about 200 to about 450 milliosmol (mOsm) and a viscosity of from about 1 centipoise to about 20 centipoises at 25° C.

15. The packaging solution of claim 14 , wherein the buffering agents are present in a packaging solution in an amount of from 0.01% to 0.8% by weight.

16. The packaging solution of claim 14 , wherein the packaging solution has a viscosity of from about 1 centipoise to about 5 centipoises at 25° C.

Assignees

• Novartis Ag

Inventors

• Chang Frank
• Holland Troy Vernon
• Moy Thomas M

Classifications

• C08F22/38

  Amides · CPC title

• C08F8/34

  Introducing sulfur atoms or sulfur-containing groups · CPC title

• C08F2810/20

  leading to a crosslinking, either explicitly or inherently · CPC title

• G02B1/04

  made of organic materials, e.g. plastics (G02B1/08 takes precedence) · CPC title

• C08F20/56

  Acrylamide; Methacrylamide · CPC title