Contact lens with a hydrophilic layer

• US 10,451,896 B2
• Filed: 07/08/2016
• Issued: 10/22/2019
• Est. Priority Date: 08/27/2012
• Status: Active Grant

• Current Assignee: Tangible Science, Llc
• Original Assignee: Tangible Science, Llc
• Inventors: Havenstrite, Karen L., McCray, Victor W., Felkins, Brandon M., Ackermann, Douglas M., Smith, Garrett C., Cook, Paul A., Luxon, Evan S., McGibbon, Andrew A.
• Primary Examiner(s): Greece, James R
• Application Number:
  US15/206,103
• Publication Number:
  US 20160320635A1
• Time in Patent Office: 1,201 Days
• Field of Search: 35915933
• CPC Class Codes: C08L 101/14 the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
• CPC Class Codes: C08L 2203/02 for biomedical use
• CPC Class Codes: C08L 2205/025 containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
• CPC Class Codes: C08L 5/08 Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
• CPC Class Codes: C08L 71/00 Compositions of polyethers obtained by reactions forming an ether link in the main chain of polyacetals C08L59/00; of epoxy resins C08L63/00; of polythioether-ethers C08L81/02; of polyether-sulfones C08L81/06; Compositions of derivatives of such polymers
• CPC Class Codes: C09D 105/08 Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
• CPC Class Codes: C09D 171/00 Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain based on polyacetals C09D159/00; based on epoxy resins C09D163/00; based on polythioether-ethers C09D181/02; based on polyethersulfones C09D181/06; Coating compositions based on derivatives of such polymers
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: G02C 2202/16 Laminated or compound lenses
• CPC Class Codes: G02C 7/049 Contact lenses having special fitting or structural features achieved by special materials or material structures

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

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 polyacrylamide species with a reactive electron pair accepting group and a second polyacrylamide species with a reactive nucleophilic group, the first polyacrylamide species being at least partially cross-linked to the second polyacrylamide species through the reactive electron pair accepting group of the first polyacrylamide species and the reactive nucleophilic group through the second polyacrylamide species.

2. The lens of claim 1, wherein the hydrogel layer has a substantially uniform chemical composition.

3. The lens of claim 1, wherein the hydrogel layer is covalently attached to the core by a sulfonyl moiety, a thioether moiety, or a sulfonyl moiety and a thioether moiety.

4. The lens of claim 1, wherein the hydrogel layer has a substantially uniform water content.

5. The lens of claim 1, wherein a thickness of the hydrogel layer is greater than a monolayer of the first polyacrylamide species.

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

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

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

9. 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.

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

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

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

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

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

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

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

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

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

19. The lens of claim 1, wherein the coated contact lens is characterized as comprising an advancing contact angle between about 20 degrees to about 50 degrees.

20. The lens of claim 1, wherein the coated contact lens is characterized as comprising an advancing contact angle between about 25 degrees to about 35 degrees.

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

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

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

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

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

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

27. The lens of claim 26, wherein the at least one active agent comprises one or more of a UV-absorbing agent, a visibility tinting agent, an antimicrobial agent, a bioactive agent, a leachable lubricant, a leachable tear-stabilizing agent, and any mixture thereof.

28. 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 polyacrylamide species with a reactive sulfonyl group and a second polyacrylamide species with a reactive amine group, the first polyacrylamide species being at least partially cross-linked to the second polyacrylamide species through a sulfonamide covalent linkage between the reactive sulfonyl group of the first polyacrylamide species and the reactive amine group of the second polyacrylamide species.

29. The lens of claim 28, wherein the hydrogel layer has a substantially uniform chemical composition.

30. The lens of claim 29, wherein the hydrogel layer is covalently attached to the core by a sulfonyl moiety, a thioether moiety, or a sulfonyl moiety and a thioether moiety.

31. The lens of claim 29, wherein at least one of the first polyacrylamide species is a branched polymer.

32. The lens of claim 28, wherein a thickness of the hydrogel layer is greater than a monolayer of the first polyacrylamide species.

33. The lens of claim 28, wherein the hydrogel layer comprises a thickness below about 100 nm.

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

35. The lens of claim 28, wherein the hydrogel layer further comprises at least one active agent.

36. The lens of claim 28, wherein the at least one active agent comprises one or more of a UV-absorbing agent, a visibility tinting agent, an antimicrobial agent, a bioactive agent, a leachable lubricant, a leachable tear-stabilizing agent, and any mixture thereof.

37. The lens of claim 28, wherein the core layer consists of silicone.

38. The lens of claim 28, wherein the core layer comprises a hydrogel.

39. The lens of claim 28, wherein the core layer is substantially free of silicone.

40. 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 comprising a first polyacrylamide species with a reactive amine group and a second polyacrylamide species with a reactive carboxyl group, the first polyacrylamide species being at least partially cross-linked to the second polyacrylamide species through an amide covalent linkage between the reactive amine group of the first polyacrylamide species and the reactive carboxyl group of the second polyacrylamide species.

41. The lens of claim 40, wherein the hydrogel layer comprises a thickness between about 0.01 microns and about 0.05 microns.

42. The lens of claim 40, wherein the hydrogel layer comprises a thickness below about 100 nm.