Wettable silicone hydrogel contact lenses

• US 9,164,298 B2
• Filed: 02/23/2012
• Issued: 10/20/2015
• Est. Priority Date: 02/28/2011
• Status: Active Grant

• Current Assignee: Coopervision International Limited (The Cooper Cos., Inc.)
• Original Assignee: Coopervision International Holding Company LP (The Cooper Cos., Inc.)
• Inventors: Hong, Ye, Yao, Li, Liu, Yuwen, Chen, Charlie, Back, Arthur
• Primary Examiner(s): PEPITONE, MICHAEL F
• Application Number:
  US13/983,577
• Publication Number:
  US 20140022506A1
• Time in Patent Office: 1,335 Days
• US Class Current: 1/1
• CPC Class Codes: C08L 101/14 the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: C08L 83/12 containing polyether sequences
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: G02C 7/049 Contact lenses having special fitting or structural features achieved by special materials or material structures

Abstract

Silicone hydrogel contact lenses are formed from the reaction product of a polymerizable composition comprising at least one acrylate-containing siloxane monomer, at least one hydrophilic vinyl-containing monomer, and at least one vinyl-containing cross-linking agent, wherein the polymerizable composition has a molar ratio of total amount of hydrophilic vinyl-containing monomer to total amount of acrylate-containing siloxane monomer of from 5:1 to 30:1, respectively. The silicone hydrogel contact lenses have good manufacturing processability, can be manufactured without the use of alcohol solvents, and have excellent surface wettability.

Claims

1. A silicone hydrogel contact lens comprising:

a polymeric lens body that is the reaction product of a polymerizable composition comprising;

a) at least one mono-functional acrylate-containing siloxane monomer having a molecular weight of less than 1000;

b) at least one bi-functional acrylate-containing siloxane monomer represented by formula (II),

2. The contact lens of claim 1, wherein the at least one hydrophilic vinyl-containing monomer is selected from N-vinyl-N-methyl acetamide (VMA), or N-vinyl pyrrolidone (NVP), or 1,4-butanediol vinyl ether (BVE), or ethylene glycol vinyl ether (EGVE), or diethylene glycol vinyl ether (DEGVE), or any combination thereof.

3. The contact lens of claim 1, wherein the at least one vinyl-containing cross-linking agent is selected from divinyl ether, or divinyl sulfone, or triallyl phthalate, or triallyl isocyanurate, or diallyl phthalate, or diethyleneglycol divinyl ether, or triethyleneglycol divinyl ether, or any combination thereof.

4. The contact lens of claim 1, wherein the at least one vinyl-containing cross-linking agent is a divinyl ether.

5. The contact lens of claim 1, wherein the bi-functional acrylate-containing siloxane monomer has a molecular weight of at least 3,000.

6. The contact lens of claim 1, wherein the bi-functional acrylate-containing siloxane monomer has a molecular weight of at least 5,000.

7. The contact lens of claim 1, wherein the mono-functional acrylate-containing siloxane monomer and the bi-functional acrylate-containing siloxane monomer are present in the polymerizable composition at a molar ratio of at least 30:

1, respectively.

8. The contact lens of claim 1, wherein the polymerizable composition further comprises at least one non-siloxane acrylate-containing monomer.

9. The contact lens of claim 8, wherein the at least one non-siloxane acrylate-containing monomer is selected from methyl methacrylate (MMA), or 2-hydroxybutyl methacrylate (HOB), or tert butyl methacrylate (tBMA), or N,N-dimethylacrylamide (DMA), or 2-hydroxyethyl methacrylate (HEMA), or ethoxyethyl methacrylamide (EOEMA), or ethylene glycol methyl ether methacrylate (EGMA), or isobornyl methacrylate (IBM), or any combination thereof.

10. The contact lens of claim 1, wherein the polymerizable composition further comprises at least one acrylate-containing cross-linking agent.

11. The contact lens of claim 10, wherein the at least one acrylate-containing cross-linking agent is selected from triethylene glycol dimethacrylate, or ethylene glycol dimethacrylate, or a combination thereof.

12. The contact lens of claim 10, wherein the polymerizable composition has a molar ratio of total amount of acrylate-containing cross-linking agent to total amount of vinyl-containing cross-linking agent of at least 3:

2, respectively.

13. The contact lens of claim 12, wherein the polymerizable composition has a molar ratio of total amount of acrylate-containing cross-linking agent to total amount of vinyl-containing cross-linking agent of from 3:

1 to 10;

1, respectively.

14. The contact lens of claim 1, wherein the polymerizable composition is substantially free of hydrophilic polymer.

15. The contact lens of claim 1 that is free of post-polymerization surface modification.

16. The contact lens of claim 1 having a wet extractable component of 2 to 8 wt. %.

17. The contact lens of claim 1 characterized by one or more of the following physical characteristics:

a) a dynamic advancing contact angle of ≦

70°

as determined using a captive bubble method;

b) an oxygen permeability of at least 60 barrers;

c) a tensile modulus from about 0.2 MPa to about 0.9 MPa;

d) an equilibrium water content from about 30% wt/wt to about 70% wt/wt;

e) an ionoflux of less than 6×

10<sup>−

3</sup> mm²/min; and

f) an energy loss from about 27 to about 45%.

18. The contact lens of claim 17, wherein the contact angle is ≦

60° and

the equilibrium water content is at least about 40% wt/wt.

19. A method of making the silicone hydrogel contact lens of claim 1 comprising:

a) polymerizing the polymerizable composition to form the polymeric lens body;

b) contacting the polymeric lens body with a washing liquid to remove unreacted or partially reacted components from the polymeric lens body; and

c) sealing the washed polymeric lens body in a package comprising a packaging solution; and

d) sterilizing the sealed package.

20. The method of claim 19, wherein the washing liquid and any other liquid used for washing the polymeric lens body are substantially free of volatile organic solvents.