Materials for use in ophthalmic applications and methods

• US 8,646,907 B2
• Filed: 09/21/2010
• Issued: 02/11/2014
• Est. Priority Date: 09/22/2009
• Status: Active Grant

• Current Assignee: Coopervision International Limited (The Cooper Cos., Inc.)
• Original Assignee: Coopervision International Holding Company LP (The Cooper Cos., Inc.)
• Inventors: Zhang, Yun, Chen, Charlie, Zhu, Peter, Ye, Ying, Qiu, Hongjin
• Primary Examiner(s): Mack, Ricky
• Assistant Examiner(s): ALEXANDER, WILLIAM R
• Application Number:
  US13/395,134
• Publication Number:
  US 20120194779A1
• Time in Patent Office: 1,239 Days
• Field of Search: 351/159.33, 351/159.62, 424/78.04, 523/106
• US Class Current: 351/159.33
• CPC Class Codes: C08J 7/16 with polymerisable compounds

Abstract

A lens body comprising at least one form of boronic acid, boronic ester or boronic anhydride is provided. The lens body is contacted with a solution comprising at least one form of TRIS. A contact lens package including the contact lens, and methods of producing and using the contact lens, are also provided.

Claims

1. A method of manufacturing a hydrogel contact lens body, comprising:

providing a lens body comprising at least one form of boronic acid, boronic ester, boronic anhydride or combination thereof; and

contacting the lens body with a contacting solution comprising at least one form of tris(hydroxymethyl)aminomethane (TRIS), and a form of poly(vinyl alcohol) (PVOH), wherein the at least one form of TRIS is present in the solution at a concentration effective to prevent gelation of the form of PVOH.

2. The method of claim 1, wherein the at least one form of the boronic acid, boronic ester, boronic anhydride or combination thereof is a boronic acid having the structure:

3. The method of claim 1, wherein the hydrogel lens body is a polymerized reaction product of a polymerizable composition, the polymerizable composition comprising at least one hydrophilic monomer, and at least one crosslinking agent;

and the polymerized reaction product is a polymer formed of polymerized units of the at least one hydrophilic monomer, and crosslinks formed by the at least one crosslinking agent.

4. The method of claim 1, wherein the at least one form of TRIS comprises a TRIS buffer system comprising at least one form of tris(hydroxymethyl)aminomethane (TRIS), and at least one form of ethylenediaminetetraacetic acid (EDTA).

5. The method of claim 1, wherein the contacting solution further comprises a tonicity adjusting agent.

6. The method of claim 1, wherein the contacting solution has an osmolarity from about 100 mOsm to about 400 mOsm.

7. The method of claim 1, wherein the contacting solution further comprises at least one surfactant.

8. The method of claim 1, wherein the at least one form of TRIS is present in the contacting solution at a concentration effective to lower an effective pKa of boronic acid moieties present on at least a surface of the lens body.

9. The method of claim 1, wherein the step of contacting the lens body with the contacting solution further comprises complexing at least a portion of boronic acid moieties present in the lens body with at least a portion of PVOH moieties present in solution.

10. The method of claim 1, wherein the step of contacting the lens body with the contacting solution comprises soaking the lens body in the contacting solution, rinsing the lens body with the contacting solution, or both soaking and rinsing the lens body.

11. The method of claim 1, wherein the step of contacting the lens body with the contacting solution comprises placing the lens body in a contact lens package with the solution, sealing the package, and sterilizing the package.

12. The method of claim 11, wherein the at least one form of TRIS is present in the solution at a concentration effective to prevent gelation of the form of PVOH over a shelf life of the sterilized package.

18. The method of claim 1, wherein the concentration of TRIS is from about 0.01% to about 10%.

13. A method of treating a hydrogel contact lens comprising:

(i) providing a contact lens comprising at least one form of boronic acid, boronic ester, boronic anhydride or combination thereof;

(ii) prior to the contact lens being worn by a user, contacting the lens body with a first contacting solution comprising at least one form of tris(hydroxymethyl)aminomethane (TRIS) and a form of poly(vinyl alcohol) (PVOH), wherein the at least one form of TRIS is present in the solution at a concentration effective to prevent gelation of the form of PVOH; and

(iii) subsequently to the contact lens being worn by the user, contacting the lens body with a second contacting solution comprising at least one form of TRIS.

14. The method of claim 13, wherein the at least one form of TRIS of the first contacting solution is the same as the at least one form of TRIS of the second contacting solution.

19. The method of claim 13, wherein the concentration of TRIS is from about 0.01% to about 10%.

15. A hydrogel contact lens product, comprising:

(i) a lens body comprising at least one form of boronic acid, boronic ester, boronic anhydride or combination thereof;

(ii) a packaging solution comprising at least one form of tris(hydroxymethyl)aminomethane (TRIS) and a form of poly(vinyl alcohol) (PVOH), wherein the at least one form of TRIS is present in the solution at a concentration effective to prevent gelation of the form of PVOH for a duration of time equivalent to a shelf life of a sterilized contact lens package;

(iii) a contact lens package base member with a cavity configured to hold the lens body and the packaging solution; and

(iv) a seal attached to the base member configured to maintain the lens body and the packaging solution in a sterile condition for the duration of time equivalent to the shelf life of the sterilized contact lens package.

16. The hydrogel contact lens product of claim 15, wherein the at least one form of TRIS is present in the packaging solution at a concentration effective to lower an effective pKa of boronic acid moieties present on at least a surface of the lens body.

17. The hydrogel contact lens product of claim 15, wherein at least a portion of boronic acid moieties present on at least a surface of the lens body are complexed with at least a portion of PVOH moieties present in the packaging solution.

20. The hydrogel contact lens product of claim 15, wherein the concentration of TRIS is from about 0.01% to about 10%.