Contact lens with a hydrophilic layer

• US 9,395,468 B2
• Filed: 08/26/2013
• Issued: 07/19/2016
• Est. Priority Date: 08/27/2012
• Status: Active Grant

• Current Assignee: Tangible Science, Llc
• Original Assignee: Ocular Dynamics, LLC
• Inventors: Havenstrite, Karen L., McCray, Victor Wayne, Felkins, Brandon McNary, Ackermann, Douglas Michael, Smith, Garrett Cale, Cook, Paul A., Luxon, Evan S., McGibbon, Andrew A.
• Primary Examiner(s): Greece, James
• Application Number:
  US13/975,868
• Publication Number:
  US 20140055741A1
• Time in Patent Office: 1,058 Days
• Field of Search: 351/159.01, 351/159.33, 351/159.73, 351/159.74
• US Class Current: 1/1
• CPC Class Codes: B29D 11/00038 Production of contact lenses
• CPC Class Codes: B29D 11/00865 Applying coatings; tinting; colouring printing, marking or copying processes B41M; identification in general G09F3/00; producing decorative effects in general B44C; positioning or marking of lenses B24B13/0055
• 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 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.