IP Library Granted Patent US 9,625,617
Granted Patent B2
US 9,625,617 · App. 15/045,855 · Granted Apr 18, 2017

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

Inventors: Charles W. Scales (St. Augustine, FL); Kevin P. McCabe (St. Augustine, FL); Brent Matthew Healy (Jacksonville, FL)
Assignee: Johnson & Johnson Vision Care, Inc.
G02B1/043
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Quick Facts
Patent No.
US 9,625,617
App. No.
15/045,855
Granted
Apr 18, 2017
Kind
B2
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.

Claims (39)

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.

Continuity (4)
Division 13899676 · May 22, 2013
Provisional Application 61651767 · May 25, 2012
Provisional Application 61771959 · Mar 4, 2013
Related Publication 20160161639A1 · Jun 9, 2016