IP Library Granted Patent US 9,395,468
Granted Patent B2
US 9,395,468 · App. 13/975,868 · Granted Jul 19, 2016

Contact lens with a hydrophilic layer

Inventors: Karen L. Havenstrite (San Francisco, CA); Victor Wayne McCray (San Jose, CA); Brandon McNary Felkins (Half Moon Bay, CA); Douglas Michael Ackermann (San Francisco, CA); Garrett Cale Smith (San Francisco, CA); Paul A. Cook (Palo Alto, CA); Evan S. Luxon (San Francisco, CA); Andrew A. McGibbon (San Francisco, CA)
Assignee: Ocular Dynamics, LLC
G02B1/043G02C7/049G02C2202/16
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Quick Facts
Patent No.
US 9,395,468
App. No.
13/975,868
Granted
Jul 19, 2016
Kind
B2
Abstract

Embodiments of the technology relate to a contact lens having a core that is covalently coated by a hydrogel layer, and to methods of making such a lens. In one aspect, embodiments provide for a coated contact lens comprising a lens core comprising an outer surface; and a hydrogel layer covalently attached to at least a portion of the outer surface, the hydrogel layer adapted to contact an ophthalmic surface, wherein the hydrogel layer comprises a hydrophilic polymer population having a first PEG species and a second PEG species, the first PEG species being at least partially cross-linked to the second PEG species.

Claims (37)

1. A coated contact lens comprising:

a lens core comprising an outer surface; and

a hydrogel layer covalently attached to at least a portion of the outer surface, the hydrogel layer adapted to contact an ophthalmic surface, wherein the hydrogel layer comprises a hydrophilic polymer population having a first PEG species and a second polymer species, the first PEG species being at least partially cross-linked to the second polymer species, wherein the first PEG species comprises a reactive electron pair accepting group and the second polymer species comprises a reactive nucleophilic group, the reactive electron pair accepting group and the reactive nucleophilic group adapted to react to thereby form cross-links between the first PEG species and the second polymer species.

2. The lens of claim 1 , wherein the hydrogel layer and core are covalently attached at the outer surface by a sulfonyl moiety.

3. The lens of claim 1 , wherein the hydrogel layer and core are covalently attached at the outer surface by a thioether moiety.

4. The lens of claim 1 , wherein the hydrogel layer and core are covalently attached at the outer surface by a sulfonyl moiety and a thioether moiety.

5. The lens of claim 1 , wherein the hydrogel layer substantially surrounds the outer surface of the core.

6. The lens of claim 1 , wherein the hydrogel layer and core are substantially optically clear.

7. The lens of claim 1 , wherein the hydrogel layer is adapted to allow optical transmission through the hydrogel layer to the ophthalmic surface.

8. The lens of claim 1 , wherein the hydrogel layer comprises a thickness between about 50 nm to about 500 nm.

9. The lens of claim 1 , wherein the hydrogel layer comprises a thickness below about 100 nm.

10. The lens of claim 1 , wherein each of the first PEG species and second polymer species is a branched species having a branch count between two to twelve branch arms.

11. The lens of claim 1 , wherein the reactive electron pair accepting group is a sulfone moiety.

12. The lens of claim 1 , wherein the reactive nucleophilic group is a thiol moiety.

13. The lens of claim 1 , wherein the reactive electron pair accepting group of the first PEG species is covalently linked to the outer surface of the core.

14. The lens of claim 1 , further comprising an advancing contact angle between about 20 degrees to about 50 degrees.

15. The lens of claim 1 , further comprising an advancing contact angle between about 25 degrees to about 35 degrees.

16. The lens of claim 1 , wherein the hydrogel layer comprises between about 80% to about 98% water by weight.

17. The lens of claim 1 , wherein the core consists of silicone.

18. The lens of claim 1 , wherein the core comprises silicone.

19. The lens of claim 1 , wherein the core is substantially free of silicone.

20. The lens of claim 1 , wherein the core comprises a hydrogel.

21. The lens of claim 1 , wherein the hydrogel layer further comprises at least one active agent.

22. The lens of claim 21 , wherein the at least one active agent is selected from the group consisting of a UV-absorbing agent, a visibility tinting agent, an antimicrobial agent, a bioactive agent, a leachable lubricant, a leachable tear-stabilizing agent, or any mixture thereof.

23. The lens of claim 1 , wherein the second polymer species is polyethylene glycol (PEG) or polyacrylamide (PAM).

24. The lens of claim 1 , wherein the hydrogel layer comprises a thickness between about 0.01 microns and about 0.05 microns.

25. A coated contact lens comprising:

a lens core comprising an outer surface; and

a hydrogel layer covalently attached to at least a portion of the outer surface, the hydrogel layer adapted to contact an ophthalmic surface, wherein the hydrogel layer comprises a hydrophilic polymer population having a first PEG species and a second polymer species the first PEG species being at least partially cross-linked to the second polymer species, wherein the first PEG species comprises a reactive sulfonyl group and the second polymer species comprises a reactive amine group, and the first PEG species and second polymer species are cross-linked by a sulfonamide covalent linkage between the first PEG species and the second polymer species.

26. The lens of claim 25 , wherein the hydrogel layer comprises a thickness below about 100 nm.

27. The lens of claim 25 , wherein the second polymer species is polyethylene glycol (PEG) or polyacrylamide (PAM).

28. The lens of claim 25 , wherein the hydrogel layer comprises a thickness between about 0.01 microns and about 0.05 microns.

29. The lens of claim 25 , wherein the hydrogel layer further comprises at least one active agent.

30. The lens of claim 25 , wherein the at least one active agent is selected from the group consisting of a UV-absorbing agent, a visibility tinting agent, an antimicrobial agent, a bioactive agent, a leachable lubricant, a leachable tear-stabilizing agent, or any mixture thereof.

31. The lens of claim 25 , wherein the core layer consists of silicone.

32. The lens of claim 25 , wherein the core layer comprises silicone.

33. The lens of claim 25 , wherein the core layer is substantially free of silicone.

Assignments (4)
CHANGE OF NAME Recorded Jul 20, 2021
From: TANGIBLE SCIENCE, LLC
To: TANGIBLE SCIENCE, INC.
Reel/Frame 056913/0728 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE NAME PREVIOUSLY RECORDED AT REEL: 039216 FRAME: 0142. ASSIGNOR(S) HEREBY CONFIRMS THE CHANGE OF NAME. Recorded Sep 23, 2016
From: OCULAR DYNAMICS, LLC
To: TANGIBLE SCIENCE, LLC
Reel/Frame 040132/0120 →
CHANGE OF NAME Recorded Jul 21, 2016
From: OCULAR DYNAMICS, LLC
To: TANGIBLE SCIENCE LLC
Reel/Frame 039216/0142 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 5, 2014
From: HAVENSTRITE, KAREN L.; MCCRAY, VICTOR WAYNE; FELKINS, BRANDON MCNARY; ACKERMANN, DOUGLAS MICHAEL; SMITH, GARRETT CALE; COOK, PAUL A.; LUXON, EVAN S.; MCGIBBON, ANDREW A.
To: OCULAR DYNAMICS, LLC
Reel/Frame 032354/0626 →
Continuity (5)
Provisional Application 61693689 · Aug 27, 2012
Provisional Application 61800835 · Mar 15, 2013
Provisional Application 61800959 · Mar 15, 2013
Provisional Application 61834813 · Jun 13, 2013
Related Publication 20140055741A1 · Feb 27, 2014