Contact lens with a hydrophilic layer

• US 10,330,951 B2
• Filed: 04/11/2016
• Issued: 06/25/2019
• Est. Priority Date: 11/15/2013
• Status: Active Grant

• Current Assignee: Tangible Science, Llc
• Original Assignee: Tangible Science, Llc
• Inventors: Havenstrite, Karen L., McCray, Victor Wayne, Felkins, Brandon McNary, Cook, Paul A.
• Primary Examiner(s): Deherrera, Kristina M
• Application Number:
  US15/095,759
• Publication Number:
  US 20160223836A1
• Time in Patent Office: 1,170 Days
• Field of Search: 35115904, 35115902
• CPC Class Codes: A61B 5/01 Measuring temperature of body parts ; Diagnostic temperature sensing, e.g. for malignant or inflamed tissue clinical contact thermometers G01K13/20
• CPC Class Codes: A61B 5/02 Detecting, measuring or recording pulse, heart rate, blood pressure or blood flow; Combined pulse/heart-rate/blood pressure determination; Evaluating a cardiovascular condition not otherwise provided for, e.g. using combinations of techniques provided for in this group with electrocardiography or electroauscultation; Heart catheters for measuring blood pressure
• CPC Class Codes: A61B 5/14507 specially adapted for measuring characteristics of body fluids other than blood devices for taking samples of body liquids A61B10/0045
• CPC Class Codes: A61B 5/14532 for measuring glucose, e.g. by tissue impedance measurement
• CPC Class Codes: B29D 11/00 Producing optical elements, e.g. lenses or prisms grinding or polishing of optical elements B24B; constructional form of optical elements G02B; optical parts of spectacles G02C7/00
• CPC Class Codes: B29D 11/00038 Production of contact lenses
• CPC Class Codes: B29D 11/00788 Producing optical films
• 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 33/10 Homopolymers or copolymers of methacrylic acid esters
• CPC Class Codes: C08L 33/26 Homopolymers or copolymers of acrylamide or methacrylamide
• CPC Class Codes: C08L 83/04 Polysiloxanes
• 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 7/04 Contact lenses for the eyes disinfection or sterilisation of contact lenses A61L12/00
• 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 coated by a hydrogel layer, and to methods of making such a lens. The coated lens can include a rigid gas permeable contact lens. The coated lens can also include a hybrid silicone and rigid gas permeable contact lens. In one aspect, embodiments provide for a coated contact lens comprising a lens core with a water equilibrium constant of less than about 2% 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 of one or more species.

Claims

1. A coated contact lens comprising:

a lens core with an equilibrium water content of less than about 2%, the 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 of one or more species.

2. The lens of claim 1, wherein the one or more species are at least partially cross-linked.

3. The lens of claim 1, wherein the lens core is substantially free of water.

4. The lens of claim 1, wherein the hydrophilic polymer population includes a first species selected from the group consisting of:

polyethylene glycol (PEG), phosphorylcholine, poly(vinyl alcohol), poly(vinylpyrrolidinone), poly(N-isopropylacrylamide) (PNIPAM), polyacrylamide (PAM), poly(2-oxazoline), polyethylenimine (PEI), poly(acrylic acid), polymethacrylate, polyelectrolytes, hyaluronic acid, chitosan, chondroitin sulfate, alginate, hydroxypropylmethylcellulose, and dextran.

5. The lens of claim 1, wherein the hydrophilic polymer population includes a second species selected from the group consisting of:

polyethylene glycol (PEG), phosphorylcholine, poly(vinyl alcohol), poly(vinylpyrrolidinone), poly(N-isopropylacrylamide) (PNIPAM), polyacrylamide (PAM), poly(2-oxazoline), polyethylenimine (PEI), poly(acrylic acid), polymethacrylate, polyelectrolytes, hyaluronic acid, chitosan, chondroitin sulfate, alginate, hydroxypropylmethylcellulose, and dextran.

6. The lens of claim 1, wherein the hydrophilic polymer population includes a first species comprising PEG.

7. The lens of claim 1, wherein the hydrophilic polymer population includes a second species comprising polyacrylamide.

8. The lens of claim 1, wherein the contact lens is a rigid gas permeable contact lens.

9. The lens of claim 1, wherein the lens core comprises a rigid gas permeable material.

10. The lens of claim 1, wherein the lens core consists essentially of a cross-linked polysiloxane.

11. The lens of claim 1, wherein the lens core is a soft contact lens.

12. The lens of claim 1, wherein the hydrogel layer has a thickness less than about 5 micron.

13. The lens of claim 1, wherein the hydrogel layer comprises a thickness less than about 50 nm.

14. The lens of claim 1, wherein the one or more species comprises a first species comprising a reactive electrophilic group or a reactive nucleophilic group and a second species comprising a reactive electrophilic group or a reactive nucleophilic group complementary to the first species, the reactive electrophilic group and the reactive nucleophilic group adapted to react to thereby form cross-links between the first species and the second species.

15. The lens of claim 14, wherein the reactive electrophilic group is selected from the group consisting of:

amino-reactive groups, sulfhydryl-reactive groups, carboxyl groups, hydroxyl groups, haloalkyl groups, dienophile groups, aldehyde or ketone groups, alkenes, epoxides, and phosphoramidites.

16. The lens of claim 14, wherein the reactive nucleophilic group is selected from the group consisting of:

amines, amino-reactive groups, sulfhydryl, sulfhydryl-reactive groups, carboxyl groups, hydroxyl groups, haloalkyl groups, dienophile groups, aldehyde or ketone groups, alkenes, epoxides, and phosphoramidites.

17. The lens of claim 14, wherein at least one of the reactive electrophilic group of the first species or the reactive electrophilic group of the second species is covalently linked to the outer surface of the lens core.

18. The lens of claim 1, wherein the lens has an advancing contact angle as measured by a captive bubble test of less than about 35 degrees.

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

20. The lens of claim 1, wherein the lens has a critical coefficient of friction of less than about 0.05.

21. The lens of claim 1, wherein the lens has a water break up time of greater than about 20 seconds.

22. The lens of claim 1, wherein the lens does not substantially denature proteins.

23. The lens of claim 1, wherein the hydrophilic polymer population further comprises at least one active agent.

24. The lens of claim 23, 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.

25. The lens of claim 1, wherein the lens has an oxygen transmissibility (DK/t) of greater than 200.

26. The lens of claim 1, wherein the lens core has a thickness of less than about 50 nm.

27. The lens of claim 1, wherein the lens core has a refractive index greater than about 1.360.

28. The lens of claim 1, wherein the lens core has a refractive index greater than about 1.420.

29. The lens of claim 1, wherein coated contact lens has a thickness of less than about 50 microns.