Lenses capable of post-fabrication power modification

• US 20030090013A1
• Filed: 06/18/2002
• Published: 05/15/2003
• Est. Priority Date: 01/12/1999
• Status: Abandoned Application

• Current Assignee: California Institute of Technology, Regents of the University of California (University of California)
• Original Assignee: California Institute of Technology
• Inventors: Grubbs, Robert H., Kornfield, Julia A., Jethmalani, Jagdish M., Sandstedt, Christian A., Schwartz, Daniel M.
• Application Number:
  US10/176,947
• Publication Number:
  US 20030090013A1
• Time in Patent Office: Days
• US Class Current: 264/1.32
• CPC Class Codes: A61F 2/1627 for changing index of refraction, e.g. by external means or by tilting
• CPC Class Codes: A61F 2/1635 for changing shape
• 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: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: G02B 3/00 Simple or compound lenses
• CPC Class Codes: G02C 2202/14 Photorefractive lens material
• CPC Class Codes: G02C 7/04 Contact lenses for the eyes disinfection or sterilisation of contact lenses A61L12/00

Abstract

The present invention relates to lenses that are capable of post-fabrication power modifications. In general, the inventive lenses comprise (i) a first polymer matrix and (ii) a refraction modulating composition that is capable of stimulus-induced polymerization dispersed therein. When at least a portion of the lens is exposed to an appropriate stimulus, the refraction modulating composition forms a second polymer matrix. The amount and location of the second polymer matrix may modify a lens characteristic such as lens power by changing its refractive index and/or by altering its shape. The inventive lenses have a number of applications in the electronics and medical fields as data storage means and as medical lenses, particularly intraocular lenses, respectively.

Claims

1. An optical element comprising:

a first polymer matrix and

a refraction modulating composition dispersed therein wherein the refraction modulating composition is capable of stimulus-induced polymerization.

2. The optical element as in claim 1 wherein the refraction modulating composition is capable of photo-induced polymerization.

3. The optical element as in claim 1 wherein the optical element is a prism.

4. The optical element as in claim 1 wherein the optical element is a lens.

5. A lens comprising:

a first polymer matrix and

a refraction modulating composition dispersed therein wherein the refraction modulating composition is capable of photo-induced polymerization.

6. The lens as in claim 5 wherein the first polymer matrix is selected from the group consisting of poly-acrylate, poly-methacrylate, poly-vinyl, poly-siloxane, and poly-phosphazene.

7. The lens as in claim 5 wherein the refraction modulating composition includes a component selected from the group consisting of an acrylate, methacrylate, vinyl, siloxane, and phosphazine.

8. The lens as in claim 5 wherein the refraction modulating composition comprises a monomer of the formula

X—

Y—

X

and a photoinitiator

wherein Y is

X is

and X¹ is

wherein;

m and n are each independently an integer and

R¹, R², R³, R⁴, R⁵, and R⁶ are each independently selected from the group consisting hydrogen, alkyl, aryl, and heteroaryl; and

Z is a photopolymerizable group.

9. The lens as in claim 6 wherein the first polymer matrix includes a poly-siloxane.

10. The lens as in claim 6 wherein the first polymer matrix includes a poly-acrylate.

11. The lens as in claim 8 wherein

R¹, R², R³, R⁴, R⁵, and R⁶ are each independently a C₁-C₁₀ alkyl or phenyl and

Z is includes a moiety selected from the group consisting of acrylate, allyloxy, cinnamoyl, methacrylate, cinnamoyl, stibenyl, and vinyl.

12. The lens as in claim 11 wherein R¹, R², and R³, R⁵, and R⁶ are selected from the group consisting of methyl, ethyl and propyl and R⁴ is phenyl.

13. The lens as in claim 11 wherein

the monomer is (i) dimethylsiloxane-diphenylsiloxane copolymer endcapped with a vinyldimethylsilane group, (ii) dimethylsiloxane-methylphenylsiloxane copolymer endcapped with a methacryloxypropyldimethylsilane group, or (iii) dimethylsiloxane encapped with a methacryloxypropyldimethylsilane group and

the photoinitiator is 2,2-dimethoxy-2-phenylacetophenone.

14. An intraocular lens comprising:

a polysiloxane matrix and a refraction modulating composition dispersed therein wherein the refraction modulating composition is capable of photo-induced polymerization.

15. The intraocular lens as in claim 14 wherein the polysiloxane matrix is poly-dimethyl siloxane endcapped with diacetoxymethylsilane.

16. The intraocular lens as in claim 14 wherein the refraction modulating composition comprises:

dimethylsiloxane-diphenylsiloxane copolymer endcapped with a vinyldimethylsilane group;

dimethylsiloxane-methylphenylsiloxane copolymer endcapped with a methacryloxypropyldimethylsilane group;

or dimethylsiloxane encapped with a methacryloxypropyldimethylsilane group; and

,

2,2-dimethoxy-2-phenylacetophenone.

17. A method of implementing an optical element having a refractive modulating composition dispersed therein, comprising:

(a) exposing at least a portion of the optical element to a stimulus whereby the stimulus induces the polymerization of the refraction modulating composition.

18. The method as in claim 17 wherein the optical element is a prism or a lens.

19. The method as in claim 17 wherein the exposed portion represents the entire optical element.

20. The method as in claim 17 further comprising

(b) waiting an interval of time;

and

(c) re-exposing the portion of the optical element to the stimulus to induce the further polymerization of the refraction modulating composition within said portion.

21. The method as in claim 20 further comprising

repeating steps (b) and (c).

22. The method as in claim 20 further comprising:

exposing the entire optical element to the stimulus.

23. A method of implementing an intraocular lens having a refractive modulating composition dispersed therein and implanted within the eye, comprising:

(a) exposing at least a portion of the lens to a light source whereby the light source induces the polymerization of the refraction modulating composition.

24. The method as in claim 23 wherein the exposed portion represents the entire intraocular lens.

25. The method as in claim 23 further comprising:

(b) waiting an interval of time; and

(c) re-exposing the portion of the lens to the light source to induce the further polymerization of the refraction modulating composition within said portion.

26. The method as in claim 23 further comprising

repeating steps (b) and (c).

27. The method as in claim 23 further comprising:

exposing the entire lens to the light source.

28. The method as in claim 23 wherein the exposed portion is the optical zone of the lens.

29. The method as in claim 23 wherein the exposed portion is the outer rim of the lens.

30. The method as in claim 23 wherein the exposed portion is along a meridian of the lens.

31. A method of implementing an intraocular lens having a refractive modulating composition dispersed therein and implanted within the eye, comprising:

(a) exposing a first portion of the lens to a light source whereby the light source induces the polymerization of the refraction modulating composition and

(b) exposing a second portion of the lens to the light source.

32. The method as in claim 31 further comprising exposing a third portion of the lens to a light source.

33. The method as in claim 31 further comprising exposing the entire lens to the light source.

34. A method for fabricating an optical element, comprising:

mixing a first polymer matrix composition with a refraction modulating composition to form a reaction mixture;

placing the reaction mixture into a mold;

polymerizing the first polymer matrix composition to form a first polymer matrix with the refraction modulating composition dispersed therein; and

,

removing said optical element from the mold.

35. A silicon compound having the general formula:

X—

Y—

X¹

wherein X and X¹ independently comprise a terminal siloxane moiety containing a group capable of stimulus induced polymerization and Y is a siloxane having the general formulas;

wherein m and n are integers and R¹, R², R³ and R⁴ are independently selected from the group consisting of hydrogen, alkyl, aryl and substituted aryl wherein said compound has a number average molecular weight of from about 100 to about 100,000.

36. The compound of claim 35 wherein Z contains a photopolymerizable group.

37. The compound of claim 35 wherein X and X¹ are selected from groups having the formulas:

38. The compound of claim 35 wherein R1, R2, R3 and R4 are independently selected from the group consisting of C1 to C10 alkyls and aryl.

39. The compound of claim 35 wherein R1, and R2 are independently selected from the group consisting of C1 to C10 alkyls and R3 and R4 are aryl.

40. The compound of claim 37 wherein R5 and R6 are independently selected from the group consisting of C1 to C10 alkyls and aryls.

41. The compound of claim 37 wherein Z contains a group selected from the group consisting of acrylate, methacrylate, allyloxy, cinnamoyl, stibenyl and vinyl.

42. The compound of claim 35 wherein Y has the formula:

43. The compound of claim 35 wherein R1, R2, R3, and R4 are methyl.

44. The compound of claim 35 wherein R1, R2, and R3 are methyl and R4 is phenyl.

45. The compound of claim 35 wherein R1, and R2 are methyl and R3, and R4 are phenyl.

46. The compound of claim 44 wherein the phenyl groups comprises about 0.0 to about 10.0 mole percent of the compound.

47. The compound of claim 44 having a number average molecular weight of about 1000 to about 15,500.

48. A compound capable of stimulus induced polymerization having the general formula:

X—

Y—

X¹

wherein X and X¹ are independently selected from the class of compounds having the formulas;

wherein Z contains a group capable of stimulus induced polymerization and R⁵ and R⁶ are independently selected from the group consisting of hydrogen, alkyl, aryl and heteoaryl; and

Y has the general formula;

wherein m and n are integers and R¹, R², R³ and R⁴ are independently selected from the group consisting of hydrogen, alkyl, aryl and substituted aryl wherein said compound has a number average molecular weight of from about 700 to about 36,000.

49. The compound of claim 48 wherein R1, R2, R3, R4, R5 and R6 are independently selected from the group consisting of C1 to C10 alkyls and phenyl

50. The compound of claim 48 wherein Z contains a photopolyrnerizable group.

51. The compound of claim 48 wherein Z contains a group selected from the group consisting of acrylate, methacrylate, allyloxy, cinnamoyl, stibenyl and vinyl.

52. The compound of claim 48 wherein R1, R2, R3, R5, and R6 are independently selected from the group consisting of methyl, ethyl and propyl and R⁴ is phenyl.

53. The compound of claim 48 wherein R1, R2, R5, and R6 are independently selected from the group consisting of methyl, ethyl and propyl and R3 and R4 is phenyl.

54. The compound of claim 49 wherein the phenyl groups comprise from about 3 to about 6 mole percent of the compound.

55. The compound of claim 49 having a number average molecular weight of from about 1000 to about 15,500.

56. A compound capable of photopolymerization having the general formula:

X—

Y—

X¹

wherein X and X¹ independently comprise a terminal siloxane moiety containing a group capable of photopolymerization and Y is a siloxane having the general formulas;

wherein m and n are integers and R¹, R², R³ and R⁴ are independently selected from the group consisting of hydrogen, alkyl, aryl and substituted aryl wherein said compound has a number average molecular weight of from about 700 to about 36,000.

57. The compound of claim 56 wherein X and X¹ are selected from groups having the formulas:

58. The compound of claim 57 wherein Z contains a group selected from the group consisting of acrylate, methacrylate, allyloxy, cinnamoyl, stibenyl and vinyl.

59. The compound of claim 57 wherein R1, R2, R3, R4, R5 and R6 are independently selected from the group consisting of C1 to C10 alkyls and aryl.

60. The compound of claim 57 wherein R1, R2, R3, R5, and R6 are independently selected from the group consisting of methyl, ethyl and propyl and R4 is aryl.

61. The compound of claim 57 wherein R1, R2, R5, and R6 are independently selected from the group consisting of methyl, ethyl and propyl and R3 and R4 is phenyl.

62. The compound of claim 60 wherein the phenyl groups comprise from about 3 to about 6 mole percent of the compound.

63. The compound of claim 60 having a number average molecular weight of from about 1000 to about 15,500.

64. A silicon based compound having the general formula.

X—

Y—

X¹

wherein X and X¹ have the general formula

wherein R⁵ and R⁶ are independently selected from the group consisting of hydrogen, alkyl, aryl and heteroaryls and Z contains a group capable of stimulus induced polymerization and Y is a siloxane having the formula

wherein m and n are intergers and R¹, R², R³ and R⁴ are independently selected from the group consisting of hydrogen, alkyl, aryl and substituted aryl.

65. The compound of claim 64 having a number average molecular weight of from about 100 to 100,000.

66. The compound of claim 64 wherein R1, R2, R3, R4, R5 and R6 are independently selected from the group consisting of C1 to C10 and aryls.

67. The compound of claim 64 wherein R1, R2, R3, R5 and R6 are independently selected from the group consisting of methyl, ethyl and propyl and R4 is phenyl.

68. The compound of claim 64 having a number averaging molecular weight of from about 1000 to 15,500.

69. A polymeric composition comprising a first polymer matrix and a silicon compound having the general formula:

X—

Y—

X¹

dispersed in the first polymer matrix wherein X and X¹ independently comprise a terminal siloxane moiety containing a group capable of stimulus induced polymerization and Y is a siloxane having the general formulas;

wherein m and n are integers and R¹, R^2, R³ and R⁴ are independently selected from the group consisting of hydrogen, alkyl, aryl and substituted aryl wherein said compound has a number average molecular weight of from about 100 to about 100,000.

70. The composition of claim 69 wherein Z contains a photopolymerizable group.

71. The composition of claim 69 wherein X and X1 are selected from groups having the formulas:

72. The composition of claim 69 wherein R1, R2, R3 and R4 are independently selected from the group consisting of C1 to C10 alkyls and phenyl.

73. The composition of claim 69 wherein R1, and R2 are independently selected from the group consisting of C1 to C10 alkyls and R3 and R4 are aryl.

74. The composition of claim 71 wherein R5 and R6 are independently selected from the group consisting of C1 to C10 alkyls and phenyl.

75. The composition of claim 71 wherein Z contains a group selected from the group consisting of acrylate, methacrylate, allyloxy, cinnamoyl, stibenyl and vinyl.

76. The composition of claim 69 wherein Y has the formula:

77. The composition of claim 69 wherein R1, R2, R3, and R4 are methyl.

78. The composition of claim 69 wherein R1, R2, and R3 are methyl and R4 is phenyl.

79. The composition of claim 69 wherein R1, and R2 are methyl and R3, and R4 are phenyl.

80. The composition of claim 79 wherein the phenyl groups comprises about 0.0 to about 10.0 mole percent of the compound.

81. The composition of claim 79 having a number average molecular weight of about 1000 to about 15,500.

82. A polymeric composition comprising a first polymer maxtrix and a silicon compound capable of stimulus induced polymerization having the general formula:

X—

Y—

X¹

dispersed in the first polymer matrix, wherein X and X¹ are independently selected from the class of compounds having the formulas;

wherein Z contains a group capable of stimulus induced polymerization and R⁵ and R⁶ are independently selected from the group consisting of hydrogen, alkyl, aryl and heteoaryl; and

Y has the general formula;

wherein m and n are integers and R¹, R², R³ and R⁴ are independently selected from the group consisting of hydrogen, alkyl, aryl and substituted aryl wherein said compound has a number average molecular weight of from about 700 to about 36,000.

83. The composition of claim 82 wherein R1, R2, R3, R4, R5 and R6 are independently selected from the group consisting of C1 to C10 alkyls and aryl.

84. The composition of claim 82 wherein Z contains a photopolymerizable group.

85. The composition of claim 82 wherein Z contains a group selected from the group consisting of acrylate, methacrylate, allyloxy, cinnamoyl, stibenyl and vinyl.

86. The composition of claim 82 wherein R1, R2, R3, R5, and R6 are independently selected from the group consisting of methyl, ethyl and propyl and R4 is phenyl.

87. The composition of claim 82 wherein R1, R2, R5, and R6 are independently selected from the group consisting of methyl, ethyl and propyl and R3 and R4 is phenyl

88. The composition of claim 83 wherein the phenyl groups comprise from about 3 to about 6 mole percent of the compound.

89. The composition of claim 83 having a number average molecular weight of from about 1000 to about 15,500.

90. A polymeric composition comprising a first polymer matrix and a silicon compound capable of photopolymerization having the general formula:

X—

Y—

X¹

dispersed in the first polymer matrix, wherein X and X¹ independently comprise a terminal siloxane moiety containing a group capable of photopolymerization and Y is a siloxane having the general formulas;

wherein m and n are integers and R¹, R², R³ and R⁴ are independently selected from the group consisting of hydrogen, alkyl, aryl and substituted aryl wherein said compound has a number average molecular weight of from about 700 to about 36,000.

91. The composition of claim 90 wherein X and X¹ are selected from groups having the formulas:

92. The composition of claim 91 wherein Z contains a group selected from the group consisting of acrylate, methacrylate, allyloxy, cinnamoyl, stibenyl and vinyl.

93. The composition of claim 92 wherein R1, R2, R3, R4, R5 and R6 are independently selected from the group consisting of C1 to C10 alkyls and phenyl.

94. The composition of claim 93 wherein R1, R2, R3, R5, and R6 are independently selected from the group consisting of methyl, ethyl and propyl and R4 is phenyl.

95. The composition of claim 94 wherein R1, R2, R5, and R6 arc independently selected from the group consisting of methyl, ethyl and propyl and R3 and R4 is phenyl.

96. The composition of claim 94 wherein the phenyl groups comprise from about 3 to about 6 mole percent of the compound.

97. The composition of claim 94 having a number average molecular weight of from about 1000 to about 15,500.

98. A polymeric composition comprising a first polymer matrix and a silicon based compound having the general formula:

X—

Y—

X¹

dispersed within the matrix, wherein X and X¹ have the general formula

Wherein R⁵ and R⁶ are independently selected from the group consisting of hydrogen, alkyl, aryl and heteroaryls and Z contains a group capable of stimulus induced polymerization and Y is a siloxane having the formula

Wherein m and n are integers and R¹, R², R³ and R⁴ are independently selected from the group consisting of hydrogen, alkyl, aryl and substituted aryl.

99. The composition of claim 98 having a number average molecular weight of from about 100 to 100,000.

100. The composition of claim 98 wherein R1, R2, R3, R4, R5 and R6 are independently selected from the group consisting of C1 to C10 and phenyl.

101. The composition of claim 98 wherein R1, R2, R3, R5 and R6 are independently selected from the group consisting of methyl, ethyl and propyl and R4 is phenyl.

102. The composition of claim 98 having a number averaging molecular weight of from about 1000 to 15,5000.