IP Library Granted Patent US 12,449,674
Granted Patent B2
US 12,449,674 · App. 17/455,879 · Granted Oct 21, 2025

Contact lens with a hydrophilic layer

Inventors: Karen L. Havenstrite (Saratoga, 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: Tangible Science, Inc.
G02C7/049C08L5/08C08L71/00C09D105/08C09D171/00G02B1/043C08L2203/02C08L2205/025G02C2202/16
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Quick Facts
Patent No.
US 12,449,674
App. No.
17/455,879
Granted
Oct 21, 2025
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 (30)

1. A method of making a hydrogel coated contact lens comprising:

reacting an outer surface of a contact lens with a first polymer species of a hydrophilic polymer solution,

wherein the first polymer species comprises an electron pair accepting moiety and a first portion of the electron pair accepting moiety forms a covalent attachment to the outer surface of the contact lens through a first nucleophilic conjugate reaction; and

reacting the first polymer species of the hydrophilic polymer solution with a second polymer species of the hydrophilic polymer solution,

wherein the second polymer species comprises a nucleophilic reactive moiety adapted to covalently link to a second portion of the electron pair accepting moiety of the first polymer species in a second nucleophilic conjugate reaction to at least partially cross-link the first polymer species and second polymer species,

wherein the first and second nucleophilic conjugate reactions are 1,4-nucleophilic addition reactions, and

wherein a hydrogel coating is formed and covalently attached to the outer surface of the contact lens by the first and second nucleophilic conjugate reactions.

2. The method of claim 1 , further comprising modifying the outer surface of the contact lens to form a plurality of reactive nucleophilic sites on the outer surface.

3. The method of claim 2 , wherein the modifying step comprises exposing the outer surface of the contact lens to a gas plasma treatment.

4. The method of claim 2 , wherein reacting the outer surface of the contact lens with the first polymer species comprises reacting at least a portion of the plurality of reactive nucleophilic sites on the outer surface with the first portion of the electron pair accepting moiety on the first polymer species.

5. The method of claim 1 , wherein the first and second nucleophilic conjugate reactions are both a Michael-type reaction.

6. The method of claim 1 , wherein both of the first and second nucleophilic conjugate reactions are click reactions.

7. The method of claim 1 , wherein the nucleophilic reactive moiety of the second polymer species is an amine group and the electron pair accepting moiety of the first polymer species is a carboxyl group, such that the first polymer species and the second polymer species are cross-linked through an amide moiety.

8. The method of claim 1 , wherein the hydrophilic polymer solution comprises substantially equivalent concentrations of the first polymer species and the second polymer species.

9. The method of claim 1 , wherein a concentration of the electron pair accepting moiety of the first polymer species exceeds a concentration of the nucleophilic reactive moiety of the second polymer species by about 1% to about 30%.

10. The method of claim 1 , wherein the reacting steps are performed at a temperature between about 20 degrees Celsius and about 40 degrees Celsius.

11. The method of claim 1 , wherein the reacting steps are performed at a pH between about 7 and about 11.

12. The method of claim 1 , wherein the hydrogel coating is substantially optically clear.

13. The method of claim 1 , wherein the contact lens comprises a core consisting of silicone.

14. The method of claim 1 , wherein the contact lens comprises a core comprising silicone.

15. The method of claim 1 , wherein the contact lens comprises a hydrogel core.

16. The method of claim 1 , wherein the first and second polymer species are 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, and dextran.

17. The method of claim 1 , wherein the hydrogel coating layer comprises a thickness between about 0.01 microns and about 0.05 microns.

18. A method of making a hydrogel coated contact lens comprising:

reacting an outer surface of a contact lens with a first polymer species of a hydrophilic polymer solution,

wherein the first polymer species comprises an electron pair accepting moiety and a first portion of the electron pair accepting moiety forms a covalent attachment to the outer surface of the contact lens through a first nucleophilic conjugate reaction; and

reacting the first polymer species of the hydrophilic polymer solution with a second polymer species of the hydrophilic polymer solution,

wherein the second polymer species comprises a nucleophilic reactive moiety adapted to covalently link to a second portion of the electron pair accepting moiety of the first polymer species in a second nucleophilic conjugate reaction to at least partially cross-link the first polymer species and second polymer species,

wherein the first and second nucleophilic conjugate reactions are Michael-type reactions, and

wherein a hydrogel coating is formed and covalently attached to the outer surface of the contact lens by the first and second nucleophilic conjugate reactions.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 30, 2024
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: TANGIBLE SCIENCE, INC.
Reel/Frame 069076/0578 →
Continuity (8)
Continuation 16593664 · Oct 4, 2019
Continuation 15206103 · Jul 8, 2016
Continuation 13975868 · Aug 26, 2013
Provisional Application 61834813 · Jun 13, 2013
Provisional Application 61800835 · Mar 15, 2013
Provisional Application 61800959 · Mar 15, 2013
Provisional Application 61693689 · Aug 27, 2012
Related Publication 20220075208A1 · Mar 10, 2022
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