Contact lenses comprising water soluble N-(2 hydroxyalkyl) (meth)acrylamide polymers or copolymers

Patent metadata

Field	Value
Publication number	US-9625617-B2
Application number	US-201615045855-A
Country	US
Kind code	B2
Filing date	Feb 17, 2016
Priority date	May 25, 2012
Publication date	Apr 18, 2017
Grant date	Apr 18, 2017

Abstract

The present invention relates to biomedical devices, and particularly contact lenses comprising a polymer having entangled therein at least one polymer comprising repeating units from N-(2-hydroxyalkyl)(meth)acrylamide.

First claim

The invention claimed is:

1. A method comprising contacting a biomedical device formed from a hydrogel with a solution comprising at least one water soluble, non-reactive hydrophilic polymer comprising less than 20 mol % anionic repeating units and repeating units derived from N-(2-hydroxyalkyl)(meth)acrylamide of Formula I

Wherein R 1 is hydrogen or methyl,
R 2 is H or a C1-4 alkyl substituted with at least one hydroxyl group; and
R 3 is a C1-4 alkyl substituted with at least one hydroxyl group;

wherein said water soluble, non-reactive hydrophilic polymer has a degree of polymerization of about 100 to about 100,000 and is free of terminal, hydrophobic polymer blocks under conditions sufficient to incorporate a lubricious effective amount of said non-reactive hydrophilic polymer in said biomedical device.

2. The method of claim 1 wherein said hydrogel is uncharged.

3. The method of claim 1 wherein said device is a contact lens and said hydrogel comprises at least one hydrophilic component.

4. The method of claim 1 wherein said non-reactive hydrophilic polymer has a degree of polymerization between about 500 and about 10,000.

5. The method of claim 1 wherein said non-reactive hydrophilic polymer is linear or branched.

6. The method of claim 1 wherein said non-reactive hydrophilic polymer has a degree of polymerization between about 500 and about 7,500.

7. The method of claim 1 wherein said non-reactive hydrophilic polymer has a degree of polymerization between about 500 and about 2000.

8. The method of claim 1 wherein said non-reactive hydrophilic polymer is not cross-linked.

9. The method of claim 1 wherein said non-reactive hydrophilic polymer is free of repeating units capable of crosslinking under free radical polymerization conditions.

10. The method of claim 1 wherein said non-reactive hydrophilic polymer is free of repeating units derived from bioactive linker group.

11. The method of claim 1 wherein said non-reactive hydrophilic polymer is either a homopolymer or a random copolymer.

12. The method of claim 1 wherein said non-reactive hydrophilic polymer comprises less than about 10 mol % anionic repeating units.

13. The method of claim 1 wherein said non-reactive hydrophilic polymer is non-ionic.

14. The method of claim 1 wherein R 3 is selected from the group consisting of, 2-hydroxypropyl, 3-hydroxypropyl, 2,3-dihydroxypropyl, 4-hydroxy butyl, 2-hydroxy-1,1-bis(hydroxymethyl)ethyl.

15. The method of claim 1 wherein said N-(2-hydroxyalky)(meth)acrylamide is selected from the group consisting of N-(2-hydroxy propyl)(meth)acrylamide, N-(3-hydroxypropyl)(meth)acrylamide, N-(2-hydroxyethyl)(meth)acrylamide, and

And mixtures thereof.

16. The method of claim 1 wherein said N-(2-hydroxyalky)(meth)acrylamide is selected from the group consisting of N-(2-hydroxypropyl)(meth)acrylamide, and N,N-bis(2-hydroxyethyl)acrylamide.

17. The method of claim 1 wherein said N-(2-hydroxyalky)(meth)acrylamide comprises N-(2-hydroxypropyl)methacrylamide.

18. The method of claim 1 wherein said solution comprises between about 0.001 and about 10% N-(2-hydroxyalkyl)(meth)acrylamide polymer, based upon all components in the solution.

19. The method of claim 1 wherein said solution comprises between about 0.005 and about 2% N-(2-hydroxyalkyl)(meth)acrylamide polymer, based upon all components in the solution.

20. The method of claim 1 wherein said contacting step further comprises heating.

21. The method of claim 20 wherein said heating comprising autoclaving.

22. The method of claim 21 wherein said device is a contact lens and said solution is a packing solution.

23. The method of claim 20 wherein said contacting step comprises heating at temperatures between about 40 and about 100° C.

24. The method of claim 1 wherein said solution comprises a buffered solution selected from the group consisting of borate buffer and phosphate buffer.

25. An ophthalmic solution comprising between about 10 ppm and about 10 wt % at least one water soluble, non-reactive hydrophilic polymer comprising less than 20 mol % anionic repeating units and repeating units derived from N-(2-hydroxyalkyl)(meth)acrylamide of Formula I

Wherein R 1 is hydrogen or methyl,
R 2 is H or a C 1-4 alkyl substituted with at least one hydroxyl group; and
R 3 is a C 1-4 alkyl substituted with at least one hydroxyl group;

wherein said water soluble, non-reactive hydrophilic polymer has a degree of polymerization of about 100 to about 100,000 and is free of terminal, hydrophobic polymer blocks.

26. The solution of claim 25 wherein said water soluble, non-reactive hydrophilic polymer is present in a concentration of about 50 ppm and about 2 wt %, based upon all components in the solution.

27. The solution of claim 25 wherein said water soluble, non-reactive hydrophilic polymer is present in a concentration of about 100 ppm and about 5,000 ppm.

28. The solution of claim 25 , wherein said solution is selected from the group consisting of saline solutions, buffered solutions, and deionized water.

29. The solution of 28 , wherein said solution is a saline solution comprising salts selected from the group consisting sodium chloride, sodium borate, sodium phosphate, sodium hydrogenphosphate, sodium dihydrogenphosphate, and corresponding potassium salts thereof.

30. The solution of 28 , wherein said water soluble, non-reactive hydrophilic polymer has a degree of polymerization between about 100 and about 100,000.

Assignees

• Johnson & Johnson Vision Care

Inventors

• Scales Charles W
• Mccabe Kevin P
• Healy Brent Matthew

Classifications

• G02B1/043 Primary

  Contact lenses · CPC title

• C08L101/14

  the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels · CPC title

• C08L33/26

  Homopolymers or copolymers of acrylamide or methacrylamide · CPC title