Biomedical devices containing internal wetting agents

• US 9,958,577 B2
• Filed: 06/25/2015
• Issued: 05/01/2018
• Est. Priority Date: 09/10/2001
• Status: Expired due to Term

• Current Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Original Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Inventors: McCabe, Kevin P., Molock, Jr., Frank F., Hill, Gregory A., Alli, Azaam, Steffen, Robert B., Vanderlaan, Douglas G., Ford, James D.
• Primary Examiner(s): Figueroa, John J
• Application Number:
  US14/750,475
• Publication Number:
  US 20150293266A1
• Time in Patent Office: 1,041 Days
• Field of Search: None
• CPC Class Codes: A61L 2430/16 for reconstruction of eye parts, e.g. intraocular lens, cornea
• 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: C08F 251/00 Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof
• CPC Class Codes: C08F 265/04 on to polymers of esters
• CPC Class Codes: C08F 271/00 Macromolecular compounds obtained by polymerising monomers on to polymers of nitrogen-containing monomers as defined in group C08F26/00
• CPC Class Codes: C08F 271/02 on to polymers of monomers containing heterocyclic nitrogen
• CPC Class Codes: C08F 283/06 on to polyethers, polyoxymethylenes or polyacetals C08F283/004 takes precedence
• CPC Class Codes: C08F 283/12 on to polysiloxanes
• CPC Class Codes: C08F 290/06 Polymers provided for in subclass C08G
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: C08F 291/00 Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: G02C 7/022 Ophthalmic lenses having special refractive features achieved by special materials or material structures G02C7/049 takes precedence

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 silicone hydrogel formed from a reaction mixture comprising a high molecular weight hydrophilic polymer;

an effective amount of an hydroxyl-functionalized silicone-containing monomer, and a mixture of crosslinkers comprising at least one hydrophilic crosslinker with two or more polymerizable functional groups and at least one hydrophobic crosslinker with two or more polymerizable functional groups.

2. The silicone hydrogel of claim 1 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.

3. The silicone hydrogel of claim 1 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.

4. The silicone hydrogel of claim 1 wherein said hydrophilic polymer comprises poly-N-vinylpyrrolidone.

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

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

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

8. The silicone hydrogel of claim 1 wherein said hydroxyl-functionalized silicone-containing monomer is a compound of Formula I or II

9. The silicone hydrogel of claim 8 wherein said hydroxyl-functionalized silicone-containing monomer 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 mixtures thereof.

10. The silicone hydrogel of claim 1 wherein the effective amount of hydroxyl-functionalized silicone-containing monomer is about 20% to about 50%.

11. The silicone hydrogel of claim 1 further comprising at least one additional silicone containing monomer.

12. The silicone hydrogel of claim 11, wherein said additional silicone containing monomers are 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.

13. The silicone hydrogel of claim 11 wherein said additional silicone containing monomers are selected from the group consisting of 3-methacryloxypropyltris(trimethylsiloxy)silane, monomethacryloxypropyl terminated polydimethylsiloxanes, polydimethylsiloxanes, 3-methacryloxypropylbis(trimethylsiloxy)methylsilane, methacryloxypropylpentamethyl disiloxane and combinations thereof.

14. The silicone hydrogel of claim 11 wherein said additional silicone containing monomers are present in an amount of 0 to about 80 weight %.

15. The silicone hydrogel of claim 11 wherein said additional silicone containing monomers are present in an amount of about 5 to about 60%.

16. The silicone hydrogel of claim 11 wherein said additional silicone containing monomers are present in an amount of about 10 to about 40%.

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

18. The silicone hydrogel of claim 11 wherein said at least one hydrophilic monomer comprises at least one acrylic group, vinyl group or a combination thereof.

19. The silicone hydrogel of claim 18 wherein said acrylic group has the formula CH₂═

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

20. The silicone hydrogel of claim 17 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.

21. The silicone hydrogel of claim 17 wherein said at least one hydrophilic monomer comprises at least one polyoxyethylene polyol having one or more of the terminal hydroxyl groups replaced with a functional group containing a polymerizable double bond.

22. The silicone hydrogel of claim 21 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.

23. The silicone hydrogel of claim 17 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.

24. The silicone hydrogel of claim 17 wherein said at least one hydrophilic monomer comprises N,N-dimethylacrylamide.

25. The silicone hydrogel of claim 17 wherein said at least one hydrophilic monomer is present in amounts of about 0 to about 70 weight %.

26. The silicone hydrogel of claim 17 wherein said at least one hydrophilic monomer is present in amounts of about 5 to about 60 weight %.

27. The silicone hydrogel of claim 17 wherein said at least one hydrophilic monomer is present in amounts of about 10 to 50 weight %.

28. The silicone 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.

29. The silicone hydrogel of claim 1 comprising about 3 to about 15 weight % high molecular weight hydrophilic polymer and about 10 to about 80 weight % hydroxyl-functionalized silicone-containing monomer.

30. The silicone hydrogel of claim 1 comprising about 5 to about 12 weight % high molecular weight hydrophilic polymer and about 20 to about 50 weight % hydroxyl-functionalized silicone-containing monomer.

31. The silicone hydrogel of claim 1 further comprising 0 to about 80 weight % at least one additional silicone containing monomer.

32. The silicone hydrogel of claim 1 further comprising about 0 to about 70 weight % at least one hydrophilic monomer.

33. The silicone hydrogel of claim 31 comprising about 5 to about 60 weight % of said at least one additional silicone containing monomer.

34. The silicone hydrogel of claim 31 comprising about 10 to about 40 weight % of said at least one additional silicone containing monomer.

35. The silicone hydrogel of claim 32 comprising about 5 to about 60 weight % of said at least one hydrophilic monomer.

36. The silicone hydrogel of claim 32 comprising about 10 to about 50 weight % of said at least one hydrophilic monomer.

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

about 5 to about 90 weight % hydroxyl-functionalized silicone containing monomer;

5 to about 60 weight % additional silicone containing monomer and 5 to about 60 weight % hydrophilic monomer.

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

about 10 to about 80 weight % hydroxyl-functionalized silicone containing monomer;

5 to about 60 weight % additional silicone containing monomer and 5 to about 60 weight % hydrophilic monomer.

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

about 20 to about 50 weight % hydroxyl-functionalized silicone containing monomer;

5 to about 60 weight % additional silicone containing monomer and 50 to about 60 weight % hydrophilic monomer.

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

about 20 to about 50 weight % hydroxyl-functionalized silicone containing monomer;

10 to about 40 weight % additional silicone containing monomer and 10 to about 50 weight % hydrophilic monomer.

41. The silicone hydrogel of claim 1 wherein said hydrophilic polymer has a weight average molecular weight of at least about 10,000 daltons.

42. The silicone hydrogel of claim 1 wherein said hydrophilic polymer comprises at least one cyclic moiety along a backbone portion of said hydrophilic polymer.

43. The silicone hydrogel of claim 1 wherein said hydrophilic polymer is selected from the group consisting of polymers comprising cyclic amides, cyclic imides and combinations thereof.

44. An ophthalmic device comprising the silicone hydrogel of claim 1.

45. The ophthalmic I-device of claim 44 further comprising an advancing dynamic contact angle of less than about 70°

.

46. The ophthalmic device of claim 44 further comprising an advancing dynamic contact angle of less than about 60°

.

47. The ophthalmic device of claim 44 further comprising, after about one day of wear, a tear film break up time of at least about 7 seconds and an oxygen permeability of at least about 50 barrers.

48. The ophthalmic device of claim 45 further comprising a modulus of less than about 90 psi.

49. The ophthalmic device of claim 45 further comprising a water content between about 10 and about 60%.

50. The ophthalmic device of claim 45 further comprising a water content between about 20 and about 55%.

51. The ophthalmic device of claim 45 further comprising a water content between about 25 and about 40%.

52. The ophthalmic device of claim 47 wherein said tear film breakup time is at least about 7 seconds after about 7 days of wear.

53. The silicone hydrogel of claim 1 wherein said hydrophilic crosslinker comprises at least one hydrophilic functional groups selected from the group consisting of polyether, amide, hydroxyl groups and combinations thereof.

54. The silicone hydrogel of claim 1 wherein said hydrophilic crosslinker is selected from tetraethyleneglycol dimethacrylate, triethyleneglycol dimethacrylate, ethyleneglycol dimethacylate, ethylenediamine dimethyacrylamide, glycerol dimethacrylate and combinations thereof.

55. The silicone hydrogel of claim 1 wherein said hydrophobic crosslinker is selected from the group consisting of multifunctional hydroxyl-functionalized silicone containing monomer, multifunctional polyether-polydimethylsiloxane block copolymers, combinations thereof and the like.

56. The silicone hydrogel of claim 1 wherein said hydrophobic crosslinker is selected from the group consisting of acryloxypropyl terminated polydimethylsiloxane (n=10 or 20), hydroxylacrylate functionalized siloxane macromer, methacryloxypropyl terminated PDMS, butanediol dimethacrylate, divinyl benzene, 1,3-bis(3-methacryloxypropyl)tetrakis(trimethylsiloxy) disiloxane and mixtures thereof.

57. The silicone hydrogel of claim 1 wherein said reaction mixture comprises from about 0.5 to about 2 weight % hydrophilic crosslinker and from about 0.01 to about 0.2 mmole/gm hydrophobic crosslinker.

58. The silicone hydrogel of claim 1 wherein said reaction mixture comprises from about 0.5 to about 2 weight % hydrophilic crosslinker and from about 0.03 to about 0.6 mmole/gm hydrophobic crosslinker.