Biomedical devices containing internal wetting agents

• US 7,052,131 B2
• Filed: 09/06/2002
• Issued: 05/30/2006
• Est. Priority Date: 09/10/2001
• Status: Active Grant

• Current Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Original Assignee: J&J Vision Care Incorporated
• Inventors: McCabe, Kevin P., Steffen, Robert B., Molock, Frank F., Hill, Gregory A., Vanderlaan, Douglas G., Alli, Azaam, Ford, James D., Young, Kent A
• Primary Examiner(s): Robertson, Jeffrey B.
• Application Number:
  US10/236,762
• Publication Number:
  US 20030125498A1
• Time in Patent Office: 1,362 Days
• Field of Search: 525/474, 528/25, 528/28, 528/33, 526/279, 524/588, 351/160.H
• US Class Current: 351/160.00H
• CPC Class Codes: A61L 27/18 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61L 27/26 Mixtures of macromolecular compounds
• CPC Class Codes: A61L 27/52 Hydrogels or hydrocolloids
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

This invention includes a wettable biomedical device containing a high molecular weight hydrophilic polymer and a hydroxyl-functionalized silicone-containing monomer.

Claims

1. A wettable silicone hydrogel comprising the reaction product of

at least one siloxane containing macromer;

at least one high molecular weight hydrophilic polymer; and

at least one compatibilizing component in an amount effective to compatibilize said at least one siloxane-containing macromer and said at least one high molecular weight hydrophilic polymer wherein said at least one compatibilizing component is selected from the group consisting of 2-propenoic acid, 2-methyl-2-hydroxy-3-[3-[1,3,3,3-tetramethyl-1-[trimethylsilyl)oxy]disiloxanyl]propoxy]propyl ester, (3-methacryloxy-2-hydroxypropyloxy)propyltris(trimethylsiloxy)silane, (2-methacryloxy-3-hydroxypropyloxy)propylbis(trimethylsiloxy)methylsilane and compounds of Formula III;

IWA-HB-[IWA-HB]_x-IWA

Wherein x is 1 to 10;

IWA is a difunctional hydrophilic polymer having a number average molecular weight of between about 1000 and about 50,000 Daltons; and

HB is a difunctional moiety comprising at least one N which is capable of hydrogen bonding and mixtures thereof.

2. The hydrogel of claim 1 wherein said siloxane containing macromer is present in an amount between about 5% to about 50%.

3. The hydrogel of claim 1 wherein the siloxane containing macromer or prepolymer is present in an amount between about 10% to about 50%.

4. The hydrogel of claim 1 wherein the siloxane containing macromer or prepolymer is present in an amount between about 15% to about 45%.

5. The hydrogel of claim 1 wherein said at least on siloxane containing macromer comprises at least one siloxane group, and at least one second group selected from the group consisting of urethane groups, alkylene groups, alkylene oxide groups, polyoxyalkalene groups, arylene groups, alkyl esters, amide groups, carbamate groups, perfluoroalkoxy groups, isocyanate groups, combinations thereof.

6. The hydrogel of claim 5 wherein said at least one siloxane containing macromers is formed via polymerizing said siloxane group with at least one acrylic or methacrylic compound.

7. The hydrogel of claim 5 wherein said at least one siloxane containing macromer is selected from the group consisting of methacrylate functionalized, silicone-fluoroether urethane macromers, methacrylate functionalized, silicone urethane macromers, styrene functionalized prepolymers of hydroxyl functional methacrylates and silicone methacrylates and vinyl carbamate functionalized polydimethylsiloxane.

8. The hydrogel of claim 1 comprising about 1% to about 15% high molecular weight hydrophilic polymer.

9. The hydrogel of claim 1 comprising about 3% to about 15% high molecular weight hydrophilic polymer.

10. The hydrogel of claim 1 comprising about 5% to about 12% high molecular weight hydrophilic polymer.

11. The silicone hydrogel of claim 10 wherein said hydrophilic polymer is selected from the group consisting of polyamides, polylactones, polyimides, polylactams, functionalized polyamides, functionalized polylactones, functionalized polyimides, functionalized polylactams, and mixtures thereof.

12. The silicone hydrogel of claim 10 wherein said hydrophilic polymer is selected from the group consisting of poly-N-vinyl pyrrolidone, poly-N-vinyl-2-piperidone, poly-N-vinyl-2-caprolactam, poly-N-vinyl-3-methyl-2-caprolactam, poly-N-vinyl-3-methyl-2-piperidone, poly-N-vinyl-4-methyl-2-piperidone, poly-N-vinyl-4-methyl-2-caprolactam, poly-N-vinyl-3-ethyl-2-pyrrolidone, and poly-N-vinyl-4,5-dimethyl-2-pyrrolidone, polyvinylimidazole, poly-N-N-dimethylacrylamide, polyvinyl alcohol, polyacrylic acid, polyethylene oxide, poly 2 ethyl oxazoline, heparin polysaccharides, polysaccharides, mixtures and copolymers thereof.

13. The hydrogel of claim 1, wherein the high molecular weight hydrophilic polymer is poly-N-vinylpyrrolidone.

14. The silicone hydrogel of claim 1 wherein said compatibilzing component is a compound of Formula I or II

15. The hydrogel of claim 1 wherein said IWA is derived from {acute over (α

)},ω

-hydroxyl terminated poly-N-vinyl pyrrolidone and {acute over (α

)},ω

-hydroxyl terminated polyoxyalkylene glycols.

16. The hydrogel of claim 1 wherein HB is a difunctional group selected from the group consisting of amides, imides, carbamates ureas, and combinations thereof.

17. The hydrogel of claim 1 wherein said compatibilizing component is present in an amount between about 5 and about 90 weight %.

18. The hydrogel of claim 1 further comprising at least one oxygen permeable component in addition to said siloxane containing macromer or prepolymer.

19. The hydrogel of claim 18 wherein said oxygen permeable component is selected from the group consisting of amide analogs of 3-methacryloxypropyltris(trimethylsiloxy)silane;

siloxane vinyl carbamate analogs, siloxane vinyl carbonate analogs, and siloxane containing monomers, combinations and oligomers thereof.

20. The hydrogel claim 18 wherein said oxygen permeable component is selected from the group consisting of 3-methacryloxypropyltris(trimethylsiloxy)silane, monomethacryloxypropyl terminated polydimethylsiloxanes, polydimethylsiloxanes, 3-methacryloxypropylbis(trimethylsiloxy)methylsilane, methacryloxypropylpentamethyl disiloxane and combinations thereof.

21. The hydrogel of claim 18 wherein said oxygen permeable component is present in an amount of 0 to about 80 weight %.

23. The hydrogel of claim 18 wherein said oxygen permeable component is present in an amount of about 10 to about 40%.

24. The hydrogel of claim 1 further comprising at least one hydrophilic monomer.

25. The hydrogel claim 24 wherein said at least one hydrophilic monomer comprises at least one acrylic group, vinyl group or a combination thereof.

26. The hydrogel of claim 27 wherein said acrylic group has the formula CH₂═

CRCOX, where R is hydrogen or C_1-6alkyl and X is O or N.

27. The hydrogel of claim 24 wherein said at least one hydrophilic monomer is selected from the group consisting of N,N-dimethylacrylamide, 2-hydroxyethyl methacrylate, glycerol methacrylate, 2-hydroxyethyl methacrylamide, polyethyleneglycol monomethacrylate, methacrylic acid, acrylic acid, N-vinyl pyrrolidone, N-vinyl-N-methyl acetamide, N-vinyl-N-ethyl acetamide, N-vinyl-N-ethyl formamide, N-vinyl formamide, hydrophilic vinyl carbonate monomers, vinyl carbamate monomers, hydrophilic oxazolone monomers, polydextran and copolymers and combinations thereof.

28. The hydrogel of claim 24 wherein said at least one hydrophilic monomer comprises at least one polyoxyethylene polyols having one or more of the terminal hydroxyl groups replaced with a functional group containing a polymerizable double bond.

29. The hydrogel of claim 24 wherein said at least one hydrophilic monomer is selected from the group consisting of polyethylene glycol, ethoxylated alkyl glucoside, and polyethylene polyols having one or more terminal polymerizable olefinic groups bonded to the polyethylene polyol.

30. The hydrogel of claim 24 wherein said at least one hydrophilic monomer is selected from the group consisting of N,N-dimethylacrylamide, 2-hydroxyethyl methacrylate, glycerol methacrylate, 2-hydroxyethyl methacrylamide, N-vinylpyrrolidone, polyethyleneglycol monomethacrylate, methacrylic acid, acrylic acid and combinations thereof.

31. The hydrogel of claim 24 wherein said at least one hydrophilic monomer comprises N,N-dimethylacrylamide.

32. The hydrogel of claim 24 wherein said at least one hydrophilic monomer is present in amounts of about 0 to about 70 weight %.

33. The hydrogel of claim 24 wherein said at least one hydrophilic monomer is present in amounts of about 5 to about 60 weight %.

34. The hydrogel of claim 24 wherein said at least one hydrophilic monomer is present in amounts of about 10 to 50 weight %.

35. The hydrogel of claim 1 comprising about 1 to about 15 weight % high molecular weight hydrophilic polymer and about 5 to about 90 weight % hydroxyl-functionalized silicone-containing monomer.

36. The hydrogel of claim 1 comprising about 1% to about 15% high molecular weight hydrophilic polymer;

about 5 to about 90 weight % compatibilizing component;

about 5 to about 50 weight % said siloxane containing macromer, 0 to about 80 weight % siloxane containing monomer and 0 to about 70 weight % hydrophilic monomer.

37. The hydrogel of claim 1 comprising about 3% to about 15% high molecular weight hydrophilic polymer;

about 10 to about 80 weight % compatibilizing component;

about 10 to about 50 weight % said siloxane containing macromer or prepolymer, 5 to about 60 weight % siloxane containing momoner and 5 to about 60 weight % hydrophilic monomer.

38. The hydrogel of claim 1 comprising about 5% to about 12% high molecular weight hydrophilic polymer;

about 15 to about 55 weight % compatibilizing component;

about 15 to about 45 weight % said siloxane containing macromer, 10 to about 40 weight % oxygen permeable component and 10 to about 50 weight % hydrophilic monomer.

39. A silicone hydrogel contact lens comprising the hydrogel of claim 1 and wherein said contact lens is not surface modified.

40. The lens of of claim 39, wherein the contact lens is a soft contact lens.

41. The lens of claim 39 wherein said lens has an advancing dynamic contact angle of less than about 70°

.

42. The lens of claim 39 wherein said lens has an advancing dynamic contact angle of less than about 60°

.

43. The lens of claim 39 wherein said lens, after about one day of wear, has a tear film break up time of at least about 7 seconds.

44. The lens of claim 39 wherein said lens further comprises a modulus of less than about 90 psi.

45. The lens of claims 39 wherein said lens further comprises a water content between about 10 and about 60%.

46. The hydrogel of claim 1 wherein said high molecular weight hydrophilic polymer is present in an amount sufficient to provide an article formed from said hydrogel with an advancing dynamic contact angle which is at least about 10% lower than a hydrogel without said hydrophilic polymer.

47. The hydrogel of claim 1 wherein said hydrogel is an interpenetrating network or a semi-interpenetrating network.

22. The hydrogel of 18 wherein said oxygen permeable component is present in an amount of about 5 to about 60%.