Interpenetrating polymer network hydrogel contact lenses

• US 7,857,447 B2
• Filed: 12/07/2006
• Issued: 12/28/2010
• Est. Priority Date: 10/05/2004
• Status: Expired due to Fees

• Current Assignee: Board of Trustees of the Leland Stanford Junior University (Stanford University)
• Original Assignee: Board of Trustees of the Leland Stanford Junior University (Stanford University)
• Inventors: Noolandl, Jaan, Ta, Christopher, Frank, Curtis W., Myung, David
• Primary Examiner(s): PREBILIC, PAUL B
• Application Number:
  US11/636,114
• Publication Number:
  US 20070126982A1
• Time in Patent Office: 1,482 Days
• Field of Search: 623/5.16, 623/6.56, 424/427, 351/160.H, 525/903, 523/106
• US Class Current: 351/160.00H
• CPC Class Codes: C08L 51/08 grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

The present invention provides interpenetrating polymer network hydrogels that have high oxygen permeability, strength, water content, and resistance to protein adsorption. The hydrogels include two interpenetrating polymer networks. The first polymer network is based on a hydrophilic telechelic macromonomer. The second polymer network is based on a hydrophilic monomer. The hydrophilic monomer is polymerized and cross-linked to form the second polymer network in the presence of the first polymer network. The telechelic macromonomer preferably has a molecular weight of between about 575 Da and about 20,000 Da. Mixtures of molecular weights may also be used. In a preferred embodiment, the hydrophilic telechelic macromonomer is PEG-diacrylate or PEG-dimethacrylate and the hydrophilic monomer is an acrylic-based monomer. The material is designed to serve as a contact lens.

Claims

1. A contact lens, comprising:

an interpenetrating network hydrogel with a first hydrophilic network interpenetrated with a second hydrophilic network, wherein said first hydrophilic network is an entangled network of self-linked hydrophilic telechelic macromonomers covalently bonded to themselves or other of said macromonomers in said first network, wherein each of said hydrophilic telechelic macromonomers is a poly(ethylene) glycol (PEG) diacrylate or poly(ethylene) glycol (PEG) dimethacrylate based telechelic macromonomer, and wherein said second network is a network of crosslinked poly(acrylic) acid.

2. The contact lens as set forth in claim 1, wherein said first network comprises at least about 50% of the reaction product of said telechelic macromonomer by dry weight.

3. The contact lens as set forth in claim 1, wherein said hydrophilic telechelic macromonomers have a molecular weight between about 575 Da and about 20,000 Da.

4. The contact lens as set forth in claim 1, wherein at least one surface of said interpenetrating polymer network hydrogel is surface modified.

5. The contact lens as set forth in claim 4, wherein said surface is modified with a layer of poly(ethylene) glycol (PEG) macromonomers, polymerized PEG macromonomers, polymerized PEG diacrylate, polymerized PEG dimethacrylate, polymerized PEG-acrylate or polymerized PEG-methacrylate.

6. The contact lens as set forth in claim 1, wherein said first network further comprises a hydrophilic monomer grafted onto said first network.

7. The contact lens as set forth in claim 6, wherein said hydrophilic monomer is acrylic acid, acrylamide, hydroxyethyl acrylamide, N-isopropylacrylamide, methacrylic acid, 2-acrylamido-2-methylpropanesulfonic acid, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate or derivatives thereof.

8. The contact lens as set forth in claim 1, wherein said second network further comprises a hydrophilic telechelic macromonomer grafted onto said second network.

9. The contact lens as set forth in claim 8, wherein said grafted hydrophilic telechelic macromonomer is PEG diacrylate or PEG dimethacrylate.

10. The contact lens as set forth in claim 1, wherein said interpenetrating network hydrogel has a tensile strength of at least about 1 MPa.

11. The contact lens as set forth in claim 1, wherein said interpenetrating network hydrogel has an oxygen permeability of at least about 15 Barrers.

12. The contact lens as set forth in claim 1, wherein said interpenetrating network hydrogel has an equilibrium water content of between about 70% and about 95%.

13. The contact lens as set forth in claim 1, wherein said interpenetrating network hydrogel is at least about 70% transparent.

14. The contact lens as set forth in claim 1, further comprising an additive for UV protection.

28. The contact lens as set forth in claim 1, wherein the molar ratio between said first network and said second network is about 1:

1 to about 1;

5000.

29. The contact lens as set forth in claim 1, wherein the weight ratio between said first network and said second network is about 10:

1 to about 1;

10.

15. An interpenetrating polymer network hydrogel, comprising:

a first hydrophilic network interpenetrated with a second hydrophilic network, wherein said first hydrophilic network is an entangled network of self-linked hydrophilic telechelic macromonomers covalently bonded to themselves or other of said macromonomers in said first network, wherein each of said hydrophilic telechelic macromonomers is a poly(ethylene) glycol (PEG) diacrylate or poly(ethylene) glycol (PEG) dimethacrylate based telechelic macromonomer, and wherein said second network is a network of crosslinked poly(acrylic) acid.

16. The interpenetrating polymer network hydrogel as set forth in claim 15, wherein said first network comprises at least about 50% of the reaction product of said telechelic macromonomer by dry weight.

17. The interpenetrating polymer network hydrogel as set forth in claim 15, wherein said hydrophilic telechelic macromonomer has a molecular weight between about 575 Da to about 20,000 Da.

18. The interpenetrating polymer network hydrogel as set forth in claim 15, wherein at least one surface of said interpenetrating polymer network hydrogel is surface modified.

19. The interpenetrating polymer network hydrogel as set forth in claim 18, wherein said surface is modified with a layer of poly(ethylene) glycol (PEG) macromonomers, polymerized PEG macromonomers, polymerized PEG diacrylate, or polymerized PEG dimethacrylate.

20. The interpenetrating polymer network hydrogel as set forth in claim 15, wherein said first network further comprises a hydrophilic monomer grafted onto said first network.

21. The interpenetrating polymer network hydrogel as set forth in claim 20, wherein said hydrophilic monomer is acrylic acid, acrylamide, hydroxyethyl acrylamide, N-isopropylacrylamide, methacrylic acid, 2-acrylamido-2-methylpropanesulfonic acid, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate or derivatives thereof.

22. The interpenetrating polymer network hydrogel as set forth in claim 15, wherein said second network further comprises a hydrophilic telechelic macromonomer grafted onto said second network.

23. The interpenetrating polymer network hydrogel as set forth in claim 22, wherein said grafted hydrophilic telechelic macromonomers are PEG diacrylate or PEG dimethacrylate.

24. The interpenetrating polymer network hydrogel as set forth in claim 15, wherein said interpenetrating network hydrogel has a tensile strength of at least about 1 MPa.

25. The interpenetrating polymer network hydrogel as set forth in claim 15, wherein said interpenetrating network hydrogel has an oxygen permeability of at least 15 Barrers.

26. The interpenetrating polymer network hydrogel as set forth in claim 15, wherein said interpenetrating network hydrogel has an equilibrium water content of between about 70% and about 95%.

27. The interpenetrating polymer network hydrogel as set forth in claim 15, wherein said interpenetrating network hydrogel is at least about 70% transparent.

30. The interpenetrating polymer network hydrogel as set forth in claim 15, wherein the molar ratio between said first network and said second network is about 1:

1 to about 1;

5000.

31. The interpenetrating polymer network hydrogel as set forth in claim 15, wherein the weight ratio between said first network and said second network is about 10:

1 to about 1;

10.