Soft contact lenses

• US 20040186248A1
• Filed: 01/28/2004
• Published: 09/23/2004
• Est. Priority Date: 03/02/1998
• Status: Abandoned Application

• Current Assignee: Annie C. Maiden, Azaam Alli, David C. Tumer, Douglas G. Vanderlaan, Frank F. Molock, James D. Ford, John B. Enns, Kevin P. Mccabe, Marcie V. Hargiss, Robert B. Steffen, Robert N. Love
• Original Assignee: Annie C. Maiden, Azaam Alli, David C. Tumer, Douglas G. Vanderlaan, Frank F. Molock, James D. Ford, John B. Enns, Kevin P. Mccabe, Marcie V. Hargiss, Robert B. Steffen, Robert N. Love
• Inventors: McCabe, Kevin P., Steffen, Robert B., Molock, Frank F., Enns, John B., Vanderlaan, Douglas G., Alli, Azaam, Ford, James D., Maiden, Annie C., Hargiss, Marcie V., Love, Robert N., Tumer, David C.
• Application Number:
  US10/766,446
• Publication Number:
  US 20040186248A1
• Time in Patent Office: Days
• US Class Current: 525/474
• CPC Class Codes: C08F 230/08 containing silicon
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: C08L 43/04 Homopolymers or copolymers of monomers containing silicon
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

A soft contact lens containing a silicone-hydrogel made by curing a reaction mixture containing a silicone-containing monomer.

Claims

1. A method of lowering the Young'"'"'s modulus or tan δ

of a silicone hydrogel comprising the step of incorporating in said hydrogel, a mono-alkyl terminated polydimethylsiloxane monomer having the structure;

2. The method of claim 1, wherein b is about 4 to about 16, R₅₈ is a monovalent group containing at least one styryl, vinyl, or methacrylate moiety, R₅₉ is methyl, R₆₀ is C_3-8alkyl group, and R₆₁ is methyl.

3. The method of claim 1, wherein b is about 8 to about 10, R₅₈ is a monovalent group containing at least one styryl, vinyl, or methacrylate moiety, R₅₉ is methyl, R₆₀ is C_3-8alkyl group, and R₆₁ is methyl.

4. The method of claim 1, wherein b is about 4 to about 16, R₅₈ is a methacrylate moiety;

each R₅₉ is methyl; and

R₆₀ is a butyl group.

5. The method of claim 1, wherein b is about 8 to about 10, R₅₈ is a methacrylate moiety;

each R₅₉ is methyl, R₆₀ is a butyl group, and R₆₁ is methyl.

6. The method of claim 1, wherein about 2 to about 70% wt, based on the total weight of reactive monomer, of the mono-alkyl terminated polydimethylsiloxane is incorporated in said silicone hydrogel.

7. The method of claim 1, wherein about 4 to about 50% wt, based on the total weight of reactive monomer, of the mono-alkyl terminated polydimethylsiloxane is incorporated in said silicone hydrogel.

8. The method of claim 1, wherein about 8 to about 40% wt, based on the total weight of reactive monomer, of the mono-alkyl terminated polydimethylsiloxane is incorporated in said silicone hydrogel.

9. The method of claim 1, wherein said silicone hydrogel additionally comprises a silicone-containing monomer other than that of claim 1 and having the structure:

10. The method of claim 1, wherein said silicone hydrogel additionally comprises 3-methacryloxypropyltris (trimethylsiloxy) silane.

11. The method of claim 9, wherein each of R₅₂, R₅₃, and R₅₄ is independently ethyl, methyl, benzyl or phenyl.

76. The method of claim 75, wherein said silicone hydrogel additionally comprises a silicone-containing monomer other than that of claim 1 and having the structure:

78. The method of claim 76, wherein each of R₅₂, R₅₃, and R₅₄ is independently ethyl, methyl, benzyl or phenyl.

12. A silicone hydrogel having a Young'"'"'s modulus of less than about 154 psi and a tan δ

of equal to or less than about 0.3 at a frequency of 1 Hz at 25°

C.

13. The silicone hydrogel of claim 12, wherein the Young'"'"'s modulus is less than about 130 psi.

14. The silicone hydrogel of claim 12, wherein the Young'"'"'s modulus is less than about 100 psi.

15. The silicone hydrogel of claim 12, wherein the Young'"'"'s modulus is less than about 70 psi.

16. The silicone hydrogel of claim 12, wherein the Young'"'"'s modulus is less than about 45 psi.

17. The silicone hydrogel of claim 12, further comprising an O₂ Dk greater than about 40 barrer.

18. The silicone hydrogel of claim 12, 13, or 17, further comprising about 2-70% wt, based on the total weight of reactive monomer, of a mono-alkyl terminated polydimethylsiloxane having the structure:

19. The silicone hydrogel of claim 18, wherein b=4 to 16, R₅₈ is a monovalent group containing at least one styryl, vinyl, or methacrylate moiety, each R₅₉ is methyl, R₆₀ is a C_3-8alkyl group, and R₆₁ is methyl.

20. The silicone hydrogel of claim 18, wherein b=8 to 10, R₅₈ is a methacrylate moiety;

each R₅₉ is methyl;

R₆₀ is a butyl group, and R₆₁ is methyl.

21. The silicone hydrogel of claim 18, wherein the mono-alkyl terminated polydimethylsiloxane is a monomethacryloxypropyl terminated polydimethylsiloxane.

22. The silicone hydrogel of claim 18, having a Young'"'"'s modulus of about 30-160 psi.

23. The silicone hydrogel of claim 18, having a Young'"'"'s modulus of about 40-130 psi.

24. A contact lens comprising a silicone hydrogel having a Young'"'"'s modulus less than about 180 psi and a tan δ

of equal to or less than about 0.25 at a frequency of 1 Hz at 25°

C.

25. The contact lens of claim 24, having a Young'"'"'s modulus of less than about 100 psi.

26. The contact lens of claim 24, further comprising an O₂ Dk greater than about 40 barrer.

27. The contact lens of claim 24, 25, or 26, further comprising about 2-70% wt, based on the total weight of reactive monomer, of a mono-alkyl terminated polydimethylsiloxane having the structure:

28. The contact lens of claim 27, wherein b=4 to 16, R₅₈ is a monovalent group containing at least one styryl, vinyl, or methacrylate moiety, each R₅₉ is methyl, R₆₀ is C_3-8alkyl group, and R₆₁ is methyl.

29. The contact lens of claim 27, wherein b=8 to 10, R₅₈ is a methacrylate moiety;

each R₅₉ is methyl, R₆₀ is a butyl group, and R₆₁ is methyl.

30. The contact lens of claim 27, wherein the mono-alkyl terminated polydimethylsiloxane is a monomethacryloxypropyl terminated polydimethylsiloxane.

31. The contact lens of claim 27, wherein said silicone hydrogel has a Young'"'"'s modulus of about 30-160 psi.

32. The contact lens of claim 27, wherein said silicone hydrogel has a Young'"'"'s modulus of about 40-130 psi.

33. The contact lens of claim 27, further comprising a surface layer that is more hydrophilic than said silicone hydrogel.

34. The contact lens of claim 33, further comprising a coating that is more hydrophilic than said silicone hydrogel.

35. The contact lens of claim 33, wherein the surface layer comprises poly(acrylic acid).

36. A silicone hydrogel contact lens comprising a (CT) of about 50 to about 160 μ

m and a Young'"'"'s modulus (E) of about 40 to about 300 pSi, wherein (E)(CT)² is less than about 1 psi·

mm².

37. The silicone hydrogel contact lens of claim 36, further comprising a tan δ

of equal to or less than about 0.3 at a frequency of 1 Hz at 25°

C.

38. The silicone hydrogel contact lens of claim 36, further comprising a O₂Dk greater than about 40 barrer.

39. The silicone hydrogel contact lens of claim 36, 37, or 38, further comprising at least 5% wt of a mono-alkyl terminated polydimethylsiloxane having the structure:

40. The silicone hydrogel contact lens of claim 39, wherein b=4 to 16, R₅₈ is a monovalent group containing at least one styryl, vinyl, or methacrylate moiety, each R₅₉ is methyl, and R₆₀ is C_3-8alkyl group.

41. The silicone hydrogel contact lens of claim 39, wherein b=8 to 10, R₅₈ is a methacrylate moiety;

each R₅₉ is methyl;

R₆₀ is a butyl group, and R₆₁ is methyl.

42. The silicone hydrogel contact lens of claim 39, wherein the mono-alkyl terminated polydimethylsiloxane is a monomethacryloxypropyl terminated polydimethylsiloxane.

43. The silicone hydrogel contact lens of claim 39, wherein the center thickness is less than about 85 μ

m.

44. The silicone hydrogel contact lens of claim 39 wherein the thickness is less than about 100 μ

m and the Young'"'"'s modulus is less than about 100 psi.

45. The silicone hydrogel contact lens of claim 39, wherein the amount of mono-alkyl terminated polydimethylsiloxane is about 20% wt.

46. The silicone hydrogel contact lens of claim 39, wherein the center thickness is less than 129 μ

m and the Young'"'"'s modulus is less than about 60 psi.

47. The silicone hydrogel contact lens of claim 39, wherein the amount of mono-alkyl terminated polydimethylsiloxane is about 30% wt.

48. A method of making a polymer comprising preparing a silicone based macromer by Group Transfer Polymerization and reacting said macromer with a polymerization mixture comprising a mono-alkyl terminated polydimethylsiloxane monomer having the structure:

49. The method of claim 48 wherein said silicone based macromer comprises a mono-alkyl terminated polydimethylsiloxane monomer having the structure:

50. The method of claim 48 wherein said polymerizable mixture comprises Si_8-10 monomethacryloxy terminated polydimethyl siloxane, a polydimethylsiloxane other than Si_8-10 monomethacryloxy terminated polydimethyl siloxane, and a hydrophilic monomer.

51. The method of claim 48, wherein said macromer is the reaction product of a reaction mixture comprising 2-(trimethylsiloxy)ethyl methacrylate, methyl methacrylate, methacryloxypropyltris(trimethylsiloxy)silane, and mono-methacryloxypropyl terminated mono-butyl terminated polydimethylsiloxane.

52. The method of claim 48, wherein the macromer is functionalized with a free radical polymerizable group.

53. The method of claim 48, wherein the reaction mixture of claim 48 is treated with a catalyst and a molecule containing both an isocyanate group and a free radical polymerizable group.

54. The method of claim 53 wherein said catalyst comprises, tin, bismuth or a tertiary amine and said molecule containing both an isocyanate group and said free radical polymerizable group is dimethyl meta-isopropenyl benzyl isocyanate.

55. A macromer useful for making silicone hydrogels comprising a Group Transfer Polymerization product of a reaction mixture comprising 2-(trimethylsiloxy)ethyl methacrylate, methyl methacrylate, methacryloxypropyltris(trimethylsiloxy)silane, and mono-methacryloxypropyl terminated mono-butyl terminated polydimethylsiloxane.

56. The macromer of claim 55, wherein the Group Transfer Polymerization product reaction mixture comprises about 19.1 moles of 2-(trimethylsiloxy)ethyl methacrylate, about 2.8 moles of methyl methacrylate, about 7.9 moles of methacryloxypropyltris(trimethylsiloxy)silane, and about 3.3 moles of mono-methacryloxypropyl terminated mono-butyl terminated polydimethylsiloxane.

57. A silicone hydrogel comprising the reaction product of a silicone based macromer Group Transfer Polymerization product and a polymerizable mixture comprising Si_8-10 monomethacryloxy terminated polydimethyl siloxane, a polydimethylsiloxane other than Si_8-10 monomethacryloxy terminated polydimethyl siloxane, and a hydrophilic monomer.

58. The silicone hydrogel of claim 57, wherein the macromer is the Group Transfer Product of a reaction mixture 2-(trimethylsiloxy)ethyl methacrylate, methyl methacrylate, methacryloxypropyltris(trimethylsiloxy)silane, and mono-methacryloxypropyl terminated mono-butyl terminated polydimethylsiloxane.

59. The silicone hydrogel of claim 57, wherein the macromer is the Group Transfer Polymerization product of reaction mixture comprising about 19.1 moles of 2-(trimethylsiloxy)ethyl methacrylate, about 2.8 moles of methyl methacrylate, about 7.9 moles of methacryloxypropyltris(trimethylsiloxy)silane, and about 3.3 moles of mono-methacryloxypropyl terminated mono-butyl terminated polydimethylsiloxane

60. The silicone hydrogel of claim 57, 58, or 59 wherein the polymerizable mixture comprises Si_8-10 monomethacryloxy terminated polydimethyl siloxane;

methacryloxypropyl tris(trimethyl siloxy) silane;

N,N-dimethyl acrylamide;

2-(trimethylsiloxy)ethyl methacrylate; and

tetraethyleneglycol dimethacrylate.

61. The silicone hydrogel of claim 60, wherein the macromer is present in an amount of about 10 to about 60 wt percent, the Si_8-10 monomethacryloxy terminated polydimethyl siloxane is present in an amount of about 0 to about 45 wt percent;

the methacryloxypropyl tris(trimethyl siloxy) silane is present in an amount of about 0 to about 40 wt percent;

the N,N-dimethyl acrylamide is present in an amount of about 5 to about 40 wt percent;

the 2-hydroxy ethyl methacrylate is present in an amount of about 0 to about 10 wt percent; and

the tetraethyleneglycol dimethacrylate is present in an amount of about 0 to about 5 wt percent.

62. The silicone hydrogel of claim 60, wherein the macromer is present in an amount of about 15 to about 25 wt percent, the Si_8-10 monomethacryloxy terminated polydimethyl siloxane is present in an amount of about 20 to about 30 wt percent;

the methacryloxypropyl tris(trimethyl siloxy) silane is present in an amount of about 15 to about 25 wt percent;

the N,N-dimethyl acrylamide is present in an amount of about 20 to about 30 wt percent;

the 2-hydroxy ethyl methacrylate is present in an amount of about 2 to about 7 wt percent; and

the tetraethyleneglycol dimethacrylate is present in an amount of about 0 to about 5 wt percent.

63. The silicone hydrogel of claim 60, 61, or 62 wherein the polymerizable mixture further comprises poly(N-vinyl pyrrolidinone).

64. The silicone hydrogel of claim 61, wherein the polymerizable mixture further comprises about 0 to about 10 wt percent poly(N-vinyl pyrrolidinone).

65. The silicone hydrogel of claim 62, wherein the polymerizable mixture further comprises about 2 to about 7 wt percent poly(N-vinyl pyrrolidinone).

66. A contact lens comprising the reaction product of a silicone based macromer Group Transfer Polymerization product and a polymerizable mixture comprising Si_8-10 monomethacryloxy terminated polydimethyl siloxane, a polydimethylsiloxane other than Si_8-10 monomethacryloxy terminated polydimethyl siloxane, and a hydrophilic monomer.

67. The contact lens of claim 66, wherein the macromer is the Group Transfer Product of a reaction mixture, comprising 2-(trimethylsiloxy)ethyl methacrylate, methyl methacrylate, methacryloxypropyltris(trimethylsiloxy)silane, and mono-methacryloxypropyl terminated mono-butyl terminated polydimethylsiloxane.

68. The contact lens of claim 66, wherein the macromer is the Group Transfer Polymerization product of reaction mixture comprising about 19.1 moles of 2-(trimethylsiloxy)ethyl methacrylate, about 2.8 moles of methyl methacrylate, about 7.9 moles of methacryloxypropyltris(trimethylsiloxy)silane, and about 3.3 moles of mono-methacryloxypropyl terminated mono-butyl terminated polydimethylsiloxane

69. The contact lens of claim 66, 67, or 68 wherein the polymerizable mixture comprises Si_8-10 monomethacryloxy terminated polydimethyl siloxane;

methacryloxypropyl tris(trimethyl siloxy) silane;

N,N-dimethyl acrylamide;

2-hydroxy ethyl methacrylate; and

tetraethyleneglycol dimethacrylate.

70. The contact lens of claim 69, wherein the macromer is present in an amount of about 10 to about 60 wt percent, the Si_5-10monomethacryloxy terminated polydimethyl siloxane is present in an amount of about 0 to about 45 wt percent;

the methacryloxypropyl tris(trimethyl siloxy) silane is present in an amount of about 0 to about 40 wt percent;

the N,N-dimethyl acrylamide is present in an amount of about 5 to about 40 wt percent;

the 2-hydroxy ethyl methacrylate is present in an amount of about 0 to about 10 wt percent; and

the tetraethyleneglycol dimethacrylate is present in an amount of about 0 to about 5 wt percent.

71. The contact lens of claim 69, wherein the macromer is present in an amount of about 15 to about 25 wt percent, the Si_8-10 monomethacryloxy terminated polydimethyl siloxane is present in an amount of about 20 to about 30 wt percent;

the methacryloxypropyl tris(trimethyl siloxy) silane is present in an amount of about 15 to about 25 wt percent;

the N,N-dimethyl acrylamide is present in an amount of about 20 to about 30 wt percent;

the 2-hydroxy ethyl methacrylate is present in an amount of about 2 to about 7 wt percent; and

the tetraethyleneglycol dimethacrylate is present in an amount of about 0 to about 5 wt percent.

72. The contact lens of claim 69, wherein the polymerizable mixture further comprises poly(N-vinyl pyrrolidinone).

73. The contact lens of claim 70, wherein the polymerizable mixture further comprises about 0 to about 10 wt percent poly(N-vinyl pyrrolidinone).

74. The contact lens of claim 71, wherein the polymerizable mixture further comprises about 2 to about 7 wt percent poly(N-vinyl pyrrolidinone).

75. A method of lowering the Young'"'"'s modulus and tan δ

of a silicone hydrogel comprising the step of incorporating in said hydrogel, a mono-alkyl terminated polydimethylsiloxane monomer having the structure;

77. The method of claim 75, wherein said silicone hydrogel additionally comprises 3-methacryloxypropyltris (trimethylsiloxy) silane.

79. The method of claim 75 wherein Young'"'"'s modulus is lowered to less than about 100 psi and tan δ

of equal to or less than about 0.25 at a frequency of 1 Hz at 25°

C.

80. The method of claim 75 wherein Young'"'"'s modulus is lowered to less than about 80 psi and tan δ

of equal to or less than about 0.25 at a frequency of 1 Hz at 25°

C.