High refractive index hydrogel compositions for ophthalmic implants

• US 20020049290A1
• Filed: 10/10/2001
• Published: 04/25/2002
• Est. Priority Date: 12/11/1998
• Status: Active Grant

• Current Assignee: David P. Vanderbilt
• Original Assignee: David P. Vanderbilt
• Inventors: Vanderbilt, David P.
• Granted Patent: US 6,657,029 B2
• Time in Patent Office: Days
• US Class Current: 526/264
• CPC Class Codes: A61L 2430/16 for reconstruction of eye parts, e.g. intraocular lens, cornea
• CPC Class Codes: A61L 27/16 obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C08F 220/26 Esters containing oxygen in addition to the carboxy oxygen
• CPC Class Codes: C08L 33/02 Homopolymers or copolymers of acids; Metal or ammonium salts thereof
• CPC Class Codes: C08L 33/14 of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

Optically transparent, high refractive index hydrogels and intraocular lenses fabricated therefrom. The preferred hydrogels have a refractive index of 1.45 or above and a water content of approximately 5 to 30 percent by weight.

Claims

1. A hydrogel composition comprising:

a high refractive index monomer;

a hydrophilic monomer present in said composition in an amount greater than that of said high refractive index monomer;

a crosslinker; and

an initiator;

whereby said hydrogel composition has a water content of approximately 5 to 30 percent by weight and a refractive index of approximately 1.45 or greater.

2. The hydrogel composition of claim 1 wherein said composition includes an ultraviolet light absorbing material.

3. The hydrogel composition of claim 1 wherein said composition includes an ultraviolet light absorbing material selected from the group consisting of beta-(4-benzotriazoyl-3-hydroxyphenoxy) ethyl acrylate, 4-(2-acryloxyethoxy)-2-hydroxybenzophenone, 4-methacryloxy-2-hydroxybenzophenone, 2-(2′

-methacryloxy-5′

-methylphenyl) benzotriazole, 2-(2′

-hydroxy-5′

-methacryoxyethylphenyl)-2H-benzotriazole, 2-[3′

-tert-Butyl -2′

-hydroxy-5′

-(3″

-methacyloyloxypropyl) phenyl]-5-chlorobenzotriazole, 2-(3′

-tert-Butyl-5′

-(3-dimethylvinylsilylpropoxy)-2′

-hydroxyphenyl]-5-methoxybenzotriazole, 2-(3′

-Allyl-2′

-hydroxy-5′

-methylphenyl)benzotriazole, 2-[3′

-tert-Butyl-2′

-hydroxy-5′

-[3″

-methacryloyloxypropoxy) phenyl]-5-methoxybenzotriazole and 2-[3′

-tert-Butyl-2′

-hydroxy-5′

-(3″

-methacryloyloxypropoxy) phenyl]-5-chlorobenzotriazole.

4. The hydrogel composition of claim 1 wherein said composition includes beta-(4-benzotriazoyl-3-hydroxyphenoxy)ethyl acrylate as an ultraviolet light absorbing material.

5. The hydrogel composition of claim 1 wherein said initiator is selected from the group consisting of azobis(isobutyronitrile), 2,2′

-azobis(2,4-dimethylvaleronitrile), 2,2′

-azobis(methylbutyronitrile), 1,1′

-azobis(cyanocyclohexane), di-t-butyl peroxide, dicumyl peroxide, t-butylcumyl peroxide, 2,5-dimethyl-2,5-bis(2-ethylhexanoylperoxy)hexane, t-butylperoxyneodecanote, t-butyl peroxy 2-ethylhexanoate, di(4-t-butyl cyclohexyl) peroxydicarbonate, t-butyl peroxypivalate, decanoyl peroxide, lauroyl peroxide, benzoyl peroxide, 2,4-pentanedione peroxide, di(n-propyi) peroxydicarbonate, t-amyl peroxyneodecanoate and t-butyl peroxyacetate.

6. The hydrogel composition of claim 1 wherein said initiator is azobis(isobutyronitrile).

7. The composition of claim 1 wherein said crosslinker is selected from the group consisting of ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate and poly(ethylene glycol) dimethacrylate.

8. The composition of claim 1 wherein said crosslinker is ethylene glycol dimethacrylate.

9. The composition of claim 1 wherein said hydrophilic monomer is a monomer represented by the formula

10. The composition of claim 1 wherein said hydrophilic monomer is selected from the group consisting of 2-hydroxyethyl methacrylate, hydroxyethoxyethyl methacrylate, hydroxydiethoxyethyl methacrylate, methoxyethyl methacrylate, methoxyethoxyethyl methacrylate, methoxydiethoxyethyl methacrylate, poly(ethylene glycol) methacrylate, methoxy-poly(ethylene glycol) methacrylate, methacrylic acid, sodium methacrylate, glycerol methacrylate, hydroxypropyl methacrylate, and hydroxybutyl methacrylate.

11. The composition of claim 1 wherein said hydrophilic monomer is 2-hydroxyethyl methacrylate.

12. The composition of claim 1 wherein said high refractive index monomer is a monomer represented by one of the formulas

13. The composition of claim 1 wherein said high refractive index monomer is selected from the group consisting of phenyl acrylate, phenyl methacrylate, benzyl acrylate, benzyl methacrylate, 2-phenylethyl acrylate, 2-phenylethyl methacrylate, 2-phenoxyethyl acrylate, 2-phenoxyethyl methacrylate, phenythioethyl acrylate, phenylthioethyl methacrylate, 2,4,6-tribromophenyl acrylate, 2,4,6-tribromophenyl methacrylate, pentabromophenyl acrylate, pentabromophenyl methacrylate, pentachlorophenyt acrylate, pentachlorophenyl methacrylate, 2,3-dibromopropyl acrylate, 2,3-dibromopropyl methacrylate, 2-naphthyl acrylate, 2-naphthyl methacrylate, 4-methoxybenzyl acrylate, 4-methoxybenzyl methacrylate, 2-benzylioxyethyl acrylate, 2-benzyloxyethyl methacrylate, 4-chlorophenoxyethyl acrylate, 4-chlorophenoxyethyl methacrylate, 2-phenoxyethoxyethyl acrylate, 2-phenoxyethoxyethyl methacrylate, N-phenyl acrylamide, N-phenyl methacrylamide, N-benzyl acrylamide, N-benzyl methacrylamide, N,N-dibenzyl acrylamide, N,N-dibenzyl methacrylamide, N-diphenylmethyl acrylamide, N-(4-methylphenyl)methyl acrylamide, N-1-naphthyl acrylamide, N-4-nitrophenyl acrylamide, N-(2-phenylethyl) acrylamide, N-triphenylmethyl acrylamide, N-(4-hydroxyphenyl) acrylamide, N,N-methylphenyl acrylamide, N,N-phenyl phenylethyl acrylamide, N-diphenylmethyl methacrylamide, N-(4-methyl phenyl)methyl methacrylamide, N-1-naphthyl methacrylamide, N-4-nitrophenyl methacrylamide, N-(2-phenylethyl) methacrylamide, N-triphenylmethyl methacrylamide, N-(4-hydroxyphenyl) methacrylamide, N,N-methylphenyl methacrylamide, N,N′

-phenyl phenylethyl methacrylamide, N-vinylcarbazole, 4-vinylpyridine, 2-vinylpyridine, styrene, 2-chlorostyrene, 3-chlorostyrene, 4-chlorostyrene, 2-bromostyrene, 3-bromostyrene, 4-bromostyrene, 2,6-dichlorostyrene, 2-iodostyrene, 3-iodostyrene, 4-iodostyrene, pentabromostyrene, 4-phenylstyrene, 1-vinyinaphthalene, 2-vinyinaphthalene, 9-vinylanthracene and 4-phenoxystyrene.

14. The composition of claim 1 wherein said high refractive index monomer and said hydrophilic monomer comprise at least about 70 percent by weight of said composition.

15. The composition of claim 1 wherein said high refractive index monomer and said hydrophilic monomer comprise approximately 75 percent by weight of said composition.

16. A composition poly(2-hydroxyethyl methacrylate-co-phenyl methacrylate).

17. A composition poly(2-hydroxyethyl methacrylate benzyl acrylate).

18. A composition poly(2-hydroxyethyl methacrylate-co-benzyl methacrylate).

19. A composition poly(2-hydroxyethyl methacrylate-co-2-phenylethyl acrylate).

20. A composition poly(2-hydroxyethyl methacrylate-co-2-phenylethyl methacrylate).

21. A composition poly(2-hydroxyethyl methacrylate-co-2-phenoxyethyl acrylate).

22. A composition poly(2-hydroxyethyl methacrylate-co-2-phenoxyethyl methacrylate).

26. The medical device of claim 25 wherein said composition includes an ultraviolet light absorbing material.

27. The medical device of claim 25 wherein said composition includes an ultraviolet light absorbing material selected from the group consisting of beta-(4-benzotriazoyl-3-hydroxyphenoxy) ethyl acrylate, 4-(2-acryloxyethoxy)-2-hydroxybenzophenone, 4-methacryloxy-2-hydroxybenzophenone, 2-(2′

-methacryloxy-5′

-methylphenyl) benzotriazole, 2-(2′

-hydroxy-5′

-methacryoxyethylphenyl)-2H-benzotriazole, 2-[3′

-tert-Butyl-2′

-hydroxy-5′

-[3″

-methacyloyloxypropyl) phenyl]-5-chlorobenzotriazole, 2-(3′

-tert-Butyl-5′

-(3-dimethylvinyisilylpropoxy)-2′

-hydroxyphenyl]-5-methoxybenzotriazole, 2-(3′

-Allyl-2′

-hydroxy-5′

-methylphenyl) benzotriazole, 2′

-[3′

-tert-Butyl-2′

-hydroxy-5′

-(3″

-methacryloyloxypropoxy) phenyl]-5-methoxybenzotriazole and 2′

-[3′

-tert-Butyl-2′

-hydroxy-5′

-(3″

-methacryloyloxypropoxy)phenyl]-5-chlorobenzotriazole.

28. The medical device of claim 25 wherein said composition includes beta-(4-benzotriazoyl-3-hydroxyphenoxy)-ethyl acrylate as an ultraviolet light absorbing material.

29. The medical device of claim 25 wherein said initiator is selected from the group consisting of azobis(isobutyronitrile), 2,2′

-azobis(2,4-dimethylvaleronitrile), 2,2′

-azobis(methylbutyronitrile), 1,1′

-azobis(cyanocyclohexane), di-t-butyl peroxide, dicumyl peroxide, t-butylcumyl peroxide, 2,5-dimethyl-2,5-bis(2-ethylhexanoylperoxy)hexane, t-butylperoxyneodecanote, t-butyl peroxy 2-ethylhexanoate, di(4-t-butyl cyclohexyl) peroxydicarbonate, t-butyl peroxypivalate, decanoyl peroxide, lauroyl peroxide, benzoyl peroxide, 2,4-pentanedione peroxide, di(n-propyl) peroxydicarbonate, t-amyl peroxyneodecanoate and t-butyl peroxyacetate.

30. The medical device of claim 25 wherein said initiator is azobis(isobutyronitrile).

31. The medical device of claim 25 wherein said crosslinker is selected from the group consisting of ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate and poly(ethylene glycol) dimethacrylate.

32. The medical device of claim 25 wherein said crosslinker is ethylene glycol dimethacrylate.

33. The medical device of claim 25 wherein said hydrophilic monomer is a monomer represented by the formula

34. The medical device of claim 25 wherein said hydrophilic monomer is selected from the group consisting of 2-hydroxyethyl methacrylate, hydroxyethoxyethyl methacrylate, hydroxydiethoxyethyl methacrylate. methoxyethyl methacrylate, methoxyethoxyethyl methacrylate , methoxydiethoxyethyl methacrylate, poly(ethylene glycol) methacrylate, methoxy-poly(ethylene glycol) methacrylate, methacrylic acid, sodium methacrylate, glycerol methacrylate, hydroxypropyl methacrylate, and hydroxybutyl methacrylate.

35. The medical device of claim 25 wherein said hydrophilic monomer is 2-hydroxyethyl methacrylate.

36. The medical device of claim 25 wherein said high refractive index monomer is a monomer represented by one of the formulas

37. The medical device of claim 25 wherein said high refractive index monomer is selected from the group consisting of phenyl acrylate, phenyl methacrylate, benzyl acrylate, benzyl methacrylate, 2-phenylethyl acrylate, 2-phenylethyl methacrylate, 2-phenoxyethyl acrylate, 2-phenoxyethyl methacrylate, phenylthioethyl acrylate, phenylthioethyl methacrylate, 2,4,6-tribromophenyl acrylate, 2,4,6-tribromophenyl methacrylate, pentabromophenyl acrylate, pentabromophenyl methacrylate, pentachlorophenyt acrylate, pentachlorophenyl methacrylate, 2,3-dibromopropyl acrylate, 2,3-dibromopropyl methacrylate, 2-naphthyl acrylate, 2-naphthyl methacrylate, 4-methoxybenzyl acrylate, 4-methoxybenzyl methacrylate, 2-benzyloxyethyl acrylate, 2-benzyloxyethyl methacrylate, 4-chlorophenoxyethyl acrylate, 4-chlorophenoxyethyl methacrylate, 2-phenoxyethoxyethyl acrylate, 2-phenoxyethoxyethyl methacrylate, N-phenyl acrylamide, N-phenyl methacrylamide, N-benzyl acrylamide, N-benzyl methacrylamide, N,N-dibenzyl acrylamide, N,N-dibenzyl methacrylamide, N-diphenylmethyl acrylamide, N-(4-methylphenyl)methyl acrylamide, N-1-naphthyl acrylamide, N-4-nitrophenyl acrylamide, N-(2-phenylethyl) acrylamide, N-triphenylmethyl acrylamide, N-(4-hydroxyphenyl) acrylamide, N,N-methylphenyl acrylamide, N,N-phenyl phenylethyl acrylamide, N-diphenylmethyl methacrylamide, N-(4-methyl phenyl)methyl methacrylamide, N-1-naphthyl methacrylamide, N-4-nitrophenyl methacrylamide, N-(2-phenylethyl) methacrylamide, N-triphenylmethyl methacrylamide, N-(4-hydroxyphenyl) methacrylamide, N,N-methylphenyl methacrylamide, N,N′

-phenyl phenylethyl methacrylamide, N-vinylcarbazole, 4-vinylpyridine, 2-vinylpyridine, styrene, 2-chlorostyrene, 3-chlorostyrene, 4-chlorostyrene, 2-bromostyrene, 3-bromostyrene, 4-bromostyrene, 2,6-dichlorostyrene, 2-iodostyrene, 3-iodostyrene, 4-iodostyrene, pentabromostyrene, 4-phenylstyrene, 1-vinylnaphthalene, 2-vinylnaphthalene, 9-vinylanthracene and 4-phenoxystyrene.

38. The medical device of claim 25 wherein said high refractive index monomer and said hydrophilic monomer comprise at least about 70 percent by weight of said composition.

39. The medical device of claim 25 wherein said high refractive index monomer and said hydrophilic monomer comprise approximately 75 percent by weight of said composition.

40. The medical device of claim 25 wherein said hydrophilic monomer is 2-hydroxyethyl methacrylate and said high refractive index monomer is phenyl methacrylate.

41. The medical device of claim 25 wherein said hydrophilic monomer is 2-hydroxyethyl methacryate and said high refractive index monomer is benzyl acrylate.

42. The medical device of claim 25 wherein said hydrophilic monomer is 2-hydroxyethyl methacrylate and said high refractive index monomer is benzyl methacrylate.

43. The medical device of claim 25 wherein said hydrophilic monomer is 2-hydroxyethyl methacrylate and said high refractive index monomer is 2-phenylethyl acrylate.

44. The medical device of claim 25 wherein said hydrophilic monomer is 2-hydroxyethyl methacrylate and said high refractive index monomer is 2-phenylethyl methacrylate.

45. The medical device of claim 25 wherein said hydrophilic monomer is 2-hydroxyethyl methacrylate and said high refractive index monomer is 2-phenoxyethyl acrylate.

46. The medical device of claim 25 wherein said hydrophilic monomer is 2-hydroxyethyl methacrylate and said high refractive index monomer is 2-phenoxyethyl methacrylate.

47. The medical device of claim 25 wherein said hydrophilic monomer is 2-hydroxyethyl methacrylate and said high refractive index monomer is N-benzyl methacrylamide.

48. The medical device of claim 25 wherein said hydrophilic monomer is 2-hydroxyethyl methacrylate and said high refractive index monomer is N-vinylcarbazole.

50. The intraocular lens of claim 49 wherein said composition includes an ultraviolet light absorbing material.

51. The intraocular lens of claim 49 wherein said composition includes an ultraviolet light absorbing material selected from the group consisting of beta-(4-benzotriazoyl-3-hydroxyphenoxy) ethyl acrylate, 4-(2-acryloxyethoxy)-2-hydroxybenzophenone, 4-methacryloxy-2-hydroxybenzophenone, 2-(2′

-methacryloxy-5′

-methylphenyl) benzotriazole, 2-(2′

-hydroxy-5′

-methacryoxyethylphenyl)-2H-benzotriazole, 2-[3′

-tert-But-2′

-hydroxy-5′

-[3″

-methacyloyloxypropyl) phenyl]-5-chlorobenzotriazole, 2-(3′

-tert-Butyl-5′

-(3-dimethylvinylsilylpropoxy)-2′

-hydroxyphenyl]-5-methoxybenzotriazole, 2-(3′

-Allyl-2′

-hydroxy-5′

-methylphenyl)benzotriazole, 2-[3′

-tert-Butyl-2′

-hydroxy-5′

-(3″

-methacryloyloxypropoxy) phenyl]-5-methoxybenzotriazole and 2-[3′

-tert-Butyl-2′

-hydroxy-5′

-(3″

-methacryloyloxypropoxy)phenyl]-5-chlorobenzotriazole.

52. The intraocular lens of claim 49 wherein said composition includes beta-(4-benzotriazoyl-3-hydroxyphenoxy)-ethyl acrylate as an ultraviolet light absorbing material.

53. The intraocular lens of claim 49 wherein said initiator is selected from the group consisting of azobis(isobutyronitrile), 2,2′

-azobis(2,4-dimethylvaleronitrile), 2,2′

-azobis(methylbutyronitrile), 1,1′

-azobis(cyanocyclohexane), di-butyl peroxide, dicumyl peroxide, t-butylcumyl peroxide, 2,5-dimethyl-2,5-bis(2-ethylhexanoylperoxy)hexane, t-butylperoxyneodecanote, t-butyl peroxy 2-ethylhexanoate, di(4-t-butyl cyclohexyl) peroxydicarbonate, t-butyl peroxypivalate, decanoyl peroxide, lauroyl peroxide, benzoyl peroxide, 2,4-pentanedione peroxide, di(n-propyl) peroxydicarbonate, t-amyl peroxyneodecanoate and t-butyl peroxyacetate.

54. The intraocular lens of claim 49 wherein said initiator is azobis(isobutyronitrile).

55. The intraocular lens of claim 49 wherein said crosslinker is selected from the group consisting of ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate and poly(ethylene glycol) dimethacrylate.

56. The intraocular lens of claim 49 wherein said crosslinker is ethylene glycol dimethacrylate.

57. The intraocular lens of claim 49 wherein said hydrophilic monomer is a monomer represented by the formula

58. The intraocular lens of claim 49 wherein said hydrophilic monomer is selected from the group consisting of 2-hydroxyethyl methacrylate, hydroxyethoxyethyl methacrylate, hydroxydiethoxyethyl methacrylate, methoxyethyl methacrylate, methoxyethoxyethyl methacrylate, methoxydiethoxyethyl methacrylate, poly(ethylene glycol) methacrylate, methoxy-poly(ethylene glycol) methacrylate, methacrylic acid, sodium methacrylate, glycerol methacrylate, hydroxypropyl methacrylate, and hydroxybutyl methacrylate.

59. The intraocular lens of claim 49 wherein said hydrophilic monomer is 2-hydroxyethyl methacrylate.

60. The intraocular lens of claim 49 wherein said high refractive index monomer is a monomer represented by one of the formulas

61. The intraocular lens of claim 49 wherein said high refractive index monomer is selected from the group consisting of phenyl acrylate, phenyl methacrylate, benzyl acrylate, benzyl methacrylate, 2-phenylethyl acrylate, 2-phenylethyl methacrylate, 2-phenoxyethyl acrylate, 2-phenoxyethyl methacrylate, phenylthioethyl acrylate, phenylthioethyl methacrylate, 2,4,6-tribromophenyl acrylate, 2,4,6-tribromophenyl methacrylate, pentabromophenyl acrylate, pentabromophenyl methacrylate, pentachlorophenyl acrylate, pentachlorophenyl methacrylate, 2,3-dibromopropyl acrylate, 2,3-dibromopropyl methacrylate, 2-naphthyl acrylate, 2-naphthyl methacrylate, 4-methoxybenzyl acrylate, 4-methoxybenzyl methacrylate, 2-benzyloxyethyl acrylate, 2-benzyloxyethyl methacrylate, 4-chlorophenoxyethyl acrylate, 4-chlorophenoxyethyl methacrylate, 2-phenoxyethoxyethyl acrylate, 2-phenoxyethoxyethyl methacrylate, N-phenyl acrylamide, N-phenyl methacrylamide, N-benzyl acrylamide, N-benzyl methacrylamide, N,N-dibenzyl acrylamide, N,N-dibenzyl methacrylamide, N-diphenylmethyl acrylamide, N-(4-methylphenyl)methyl acrylamide, N-1-naphthyl acrylamide, N-4-nitrophenyl acrylamide, N-(2-phenylethyl) acrylamide, N-triphenylmethyl acrylamide, N-(4-hydroxyphenyl) acrylamide, N,N-methylphenyl acrylamide, N,N-phenyl phenylethyl acrylamide, N-diphenylmethyl methacrylamide, N-(4-methyl phenyl)methyl methacrylamide, N-1-naphthyl methacrylamide, N-4-nitrophenyl methacrylamide, N-(2-phenylethyl) methacrylamide, N-triphenylmethyl methacrylamide, N-4-hydroxyphenyl) methacrylamide, N,N-methylphenyl methacrylamide, N,N′

-phenyl phenylethyl methacrylamide, N-vinylcarbazole, 4-vinylpyridine, 2-vinylpyridine, styrene, 2-chlorostyrene, 3-chlorostyrene, 4-chlorostyrene, 2-bromostyrene, 3-bromostyrene, 4-bromostyrene, 2,6-dichlorostyrene, 2-iodostyrene, 3-iodostyrene, 4-iodostyrene, pentabromostyrene, 4-phenylstyrene, 1-vinylnaphthalene, 2-vinylnaphthalene, 9-vinylanthracene and 4-phenoxystyrene.

62. The intraocular lens of claim 49 wherein said high refractive index monomer and said hydrophilic monomer comprise at least about 70 percent by weight of said composition.

63. The intraocular lens of claim 49 wherein said high refractive index monomer and said hydrophilic monomer comprise approximately 75 percent by weight of said composition.

64. The intraocular lens of claim 49 wherein said hydrophilic monomer is 2-hydroxyethyl methacrylate and said high refractive index monomer is phenyl methacrylate.

65. The intraocular lens of claim 49 wherein said hydrophilic monomer is 2-hydroxyethyl methacrylate and said high refractive index monomer is benzyl acrylate.

66. The intraocular lens of claim 49 wherein said hydrophilic monomer is 2-hydroxyethyl methacrylate and said high refractive index monomer is benzyl methacrylate.

67. The intraocular lens of claim 49 wherein said hydrophilic monomer is 2-hydroxyethyl methacrylate and said high refractive index monomer is 2-phenylethyl acrylate.

68. The intraocular lens of claim 49 wherein said hydrophilic monomer is 2-hydroxyethyl methacrylate and said high refractive index monomer is 2-phenylethyl methacrylate.

69. The intraocular lens of claim 49 wherein said hydrophilic monomer is 2-hydroxyethyl methacrylate and said high refractive index monomer is 2-phenoxyethyl acrylate.

70. The intraocular lens of claim 49 wherein said hydrophilic monomer is 2-hydroxyethyl methacrylate and said high refractive index monomer is 2-phenoxyethyl methacrylate.

71. The intraocular lens of claim 49 wherein said hydrophilic monomer is 2-hydroxyethyl methacrylate and said high refractive index monomer is N-benzyl methacrylamide.

72. The intraocular lens of claim 49 wherein said hydrophilic monomer is 2-hydroxyethyl methacrylate and said high refractive index monomer is N-vinylcarbazole.

23. A composition poly(2-hydroxyethyl methacrylate-co-N-benzyl methacrylamide).

24. A composition poly(2-hydroxyethyl methacrylate-co-N-vinylcarbazole).

25. A medical device manufactured from a composition comprising:

a high refractive index monomer;

a hydrophilic monomer present in said composition in an amount greater than that of said high refractive index monomer;

a crosslinker; and

an initiator;

whereby said hydrogel composition has a water content of approximately 5 to 30 percent by weight and a refractive index of approximately 1.45 or greater.

49. An intraocular lens manufactured from a composition comprising:

a high refractive index monomer;

a hydrophilic monomer present in said composition in an amount greater than that of said high refractive index monomer;

a crosslinker; and

an initiator;

whereby said hydrogel composition has a water content of approximately 5 to 30 percent by weight and a refractive index of approximately 1.45 or greater.

73. A method of making a hydrogel composition comprising:

polymerizing polymerization materials which include a high refractive index monomer, a hydrophilic monomer present in an amount greater than that of said high refractive index monomer, an initiator and a crosslinker;

whereby said hydrogel composition has a water content of approximately 5 to 30 percent by weight and a refractive index of approximately 1.45 or greater.

74. The method of claim 73 wherein said polymerization materials include an ultraviolet light absorbing material.

75. The method of claim 73 wherein said polymerization materials include an ultraviolet light absorbing material selected from the group consisting of beta-(4-benzotriazoyl-3-hydroxyphenoxy) ethyl acrylate, 4-(2-acryloxyethoxy)-2-hydroxybenzophenone, 4-methacryloxy-2-hydroxybenzophenone, 2-(2′

-methacryloxy-5′

-methylphenyl) benzotriazole, 2-(2′

-hydroxy-5′

-methacryoxyethylphenyl)-2H-benzotriazole, 2-[3′

-tert-Butyl-2′

-hydroxy-5′

-(3″

-methacyloyloxypropyl)phenyl]-5-chlorobenzotriazole, 2-(3′

-tert-Butyl-5′

-[3-dimethylvinylsilylpropoxy)-2′

-hydroxyphenyl]-5-methoxybenzotriazole, 2-(3′

-Allyl-2′

-hydroxy-5′

-methylphenyl) benzotriazole, 2-[3′

-tert-Butyl-2′

-hydroxy-5′

-(3″

-methacryloyloxypropoxy) phenyl]-5-methoxybenzotriazole and 2-[3′

-tert-Butyl-2′

-hydroxy-5′

-(3″

-methacryloyloxypropoxy)phenyl]-5-chlorobenzotriazole.

76. The method of claim 73 wherein said polymerization materials include beta-(4-benzotriazoyl-3-hydroxyphenoxy)-ethyl acrylate as an ultraviolet light absorbing material.

77. The method of claim 73 wherein said initiator is selected from the group consisting of azobis(isobutyronitrile), 2,2′

-azobis(2,4-dimethylvaleronitrile), 2,2′

-azobis(methylbutyronitrile), 1,1′

-azobis(cyanocyclohexane), di-t-butyl peroxide, dicumyl peroxide, t-butylcumyl peroxide, 2,5-dimethyl-2,5-bis(2-ethylhexanoylperoxy) hexane, t-butylperoxyneodecanote, t-butyl peroxy 2-ethylhexanoate, di(4-t-butyl cyclohexyl) peroxydicarbonate, t-butyl peroxypivalate, decanoyl peroxide, lauroyl peroxide, benzoyl peroxide, 2,4-pentanedione peroxide, di(n-propyl)peroxydicarbonate, t-amyl peroxyneodecanoate and t-butyl peroxyacetate.

78. The method of claim 73 wherein said initiator is azobis(isobutyronitrile).

79. The method of claim 73 wherein said crosslinker is selected from the group consisting of ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate and poly(ethylene glycol) dimethacrylate.

80. The method of claim 73 wherein said crosslinker is ethylene glycol dimethacrylate.

81. The method of claim 73 wherein said hydrophilic monomer is a monomer represented by the formula

82. The method of claim 73 wherein said hydrophilic monomer is selected from the group consisting of 2-hydroxyethyl methacrylate, hydroxyethoxyethyl methacrylate, hydroxydiethoxyethyl methacrylate, methoxyethyl methacrylate, methoxyethoxyethyl methacrylate, methoxydiethoxyethyl methacrylate, poly(ethylene glycol) methacrylate, methoxy-poly(ethylene glycol) methacrylate, methacrylic acid, sodium methacrylate, glycerol methacrylate, hydroxypropyl methacrylate, and hydroxybutyl methacrylate.

83. The method of claim 73 wherein said hydrophilic monomer is 2-hydroxyethyl methacrylate.

84. The method of claim 73 wherein said high refractive index monomer is a monomer represented by one of the formulas

85. The method of claim 73 wherein said high refractive index monomer is selected from the group consisting of phenyl acrylate, phenyl methacrylate, benzyl acrylate, benzyl methacrylate, 2-phenylethyl acrylate, 2-phenylethyl methacrylate, 2-phenoxyethyl acrylate, 2-phenoxyethyl methacrylate, phenylthioethyl acrylate, phenylthioethyl methacrylate, 2,4,6-tribromophenyl acrylate, 2,4,6-tribromophenyl methacrylate, pentabromophenyl acrylate, pentabromophenyl methacrylate, pentachlorophenyl acrylate, pentachlorophenyl methacrylate, 2,3-dibromopropyl acrylate, 2,3-dibromopropyl methacrylate, 2-naphthyl acrylate, 2-naphthyl methacrylate, 4-methoxybenzyl acrylate, 4-methoxybenzyl methacrylate, 2-benzyloxyethyl acrylate, 2-benzyloxyethyl methacrylate, 4-chlorophenoxyethyl acrylate, 4-chlorophenoxyethyl methacrylate, 2-phenoxyethoxyethyl acrylate, 2-phenoxyethoxyethyl methacrylate, N-phenyl acrylamide, N-phenyl methacrylamide, N-benzyl acrylamide, N-benzyl methacrylamide, N,N-dibenzyl acrylamide, N,N-dibenzyl methacrylamide, N-diphenylmethyl acrylamide, N-(4-nitrophenyl)methyl acrylamide, N-(2-naphthyl acrylamide, N-4-nitrophenyl acrylamide, N-(2-phenylethyl) acrylamide, N-triphenylmethyl acrylamide, N-(4-hydroxyphenyl) acrylamide, N,N-methylphenyl acrylamide, N,N-phenyl phenylethyl acrylamide, N-diphenylmethyl methacrylamide, N-(4-methyl phenyl)methyl methacrylamide, N-1-naphthyl methacrylamide, N-4-nitrophenyl methacrylamide, N-(2-phenylethyl) methacrylamide, N-triphenylmethyl methacrylamide, N-4-hydroxyphenyl) methacrylamide, N,N-methylphenyl methacrylamide, N,N′

- phenyl phenylethyl methacrylamide, N-vinylcarbazole, 4-vinylpyridine, 2-vinylpyridine, styrene, 2-chlorostyrene, 3-chlorostyrene, 4-chlorostyrene, 2-bromostyrene, 3-bromostyrene, 4-bromostyrene, 2,6-dichlorostyrene, 2-iodostyrene, 3-iodostyrene, 4-iodostyrene, pentabromostyrene, 4-phenylstyrene, 1-vinylnaphthalene, 2-vinylnaphthalene, 9-vinylanthracene and 4-phenoxystyrene.

86. The method of claim 73 wherein said high refractive index monomer and said hydrophilic monomer comprise at least about 70 percent by weight of said composition.

87. The method of claim 73 wherein said high refractive index monomer and said hydrophilic monomer comprise approximately 75 percent by weight of said composition.

88. A method of making an intraocular lens from a hydrogel composition comprising:

lathing a hydrogel composition, polymerized from polymerization materials including a high refractive index monomer, a hydrophilic monomer present in an amount greater than that of said high refractive index monomer, an initiator and a crosslinker, into the form of an intraocular lens;

whereby said intraocular lens has a water content of approximately 5 to 30 percent by weight and a refractive index of approximately 1.45 or greater.

89. The method of claim 88 wherein said polymerization materials include an ultraviolet light absorbing material.

90. The method of claim 88 wherein said polymerization materials include an ultraviolet light absorbing material selected from the group consisting of beta-(4-benzotriazoyl-3-hydroxyphenoxy) ethyl acrylate, 4-(2-acryloxyethoxy)-2-hydroxybenzophenone, 4-methacryloxy-2-hydroxybenzophenone, 2-(2′

-methacryloxy-5′

-methylphenyl) benzotriazole, 2-(2-hydroxy-5′

-methacryoxyethylphenyl)-2H-benzotriazole, 2-[3′

-tert-Butyl-2′

-hydroxy-5′

-(3″

-methacyloyloxypropyl) phenyl]-5-chlorobenzotriazole, 2-[3′

-tert-Butyl-5′

-(3-dimethylvinyisilylpropoxy)-2′

-hydroxyphenyl]-5-methoxybenzotriazole, 2-(3′

-Allyl-2′

-hydroxy-5′

-methylphenyl)benzotriazole, 2-[3′

-tert-Butyl-2′

hydroxy-5′

-(3″

-methacryloyloxypropoxy)phenyl]-5-methoxybenzotriazole and 2-[3′

-tert-Butyl-2′

-hydroxy-5′

-(3″

-methacryloxypropoxy)phenyl]-5-chlorobenzotriazole.

91. The method of claim 88 wherein said polymerization materials include beta-(4-benzotriazoyl-3-hydroxyphenoxy)-ethyl acrylate as an ultraviolet light absorbing material.

92. The method of claim 88 wherein said initiator is selected from the group consisting of azobis(isobutyronitrile), 2,2′

-azobis(2,4-dimethylvaleronitrile), 2,2′

-azobis(methylbutyronitrile), 1,1′

-azobis(cyanocyclohexane), di-t-butyl peroxide, dicumyl peroxide, t-butylcumyl peroxide, 2,5-dimethyl-2,5-bis(2-ethylhexanoylperoxy) hexane, t-butylperoxyneodecanote, t-butyl peroxy 2-ethylhexanoate, di(4-t-butyl cyclohexyl) peroxydicarbonate, t-butyl peroxypivalate, decanoyl peroxide, lauroyl peroxide, benzoyl peroxide, 2,4-pentanedione peroxide, di(n-propyl)peroxydicarbonate, t-amyl peroxyneodecanoate and t-butyl peroxyacetate.

93. The method of claim 88 wherein said initiator is azobis(isobutyronitrile).

94. The method of claim 88 wherein said crosslinker is selected from the group consisting of ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate and poly(ethylene glycol) dimethacrylate.

95. The method of claim 88 wherein said crosslinker is ethylene glycol dimethacrylate.

96. The method of claim 88 wherein said hydrophilic monomer is a monomer represented by the formula

97. The method of claim 88 wherein said hydrophilic monomer is selected from the group consisting of 2-hydroxyethyl methacrylate, hydroxyethoxyethyl methacrylate, hydroxydiethoxyethyl methacrylate, methoxyethyl methacrylate, methoxyethoxyethyl methacrylate, methoxydiethoxyethyl methacrylate, poly(ethylene glycol) methacrylate, methoxy-poly(ethylene glycol) methacrylate, methacrylic acid, sodium methacrylate, glycerol methacrylate, hydroxypropyl methacrylate, and hydroxybutyl methacrylate.

98. The method of claim 88 wherein said hydrophilic monomer is 2-hydroxyethyl methacrylate.

99. The method of claim 88 wherein said high refractive index monomer is a monomer represented by one of the formulas

100. The method of claim 88 wherein said high refractive index monomer is selected from the group consisting of phenyl acrylate, phenyl methacrylate, benzyl acrylate, benzyl methacrylate, 2-phenylethyl acrylate, 2-phenylethyl methacrylate, 2-phenoxyethyl acrylate, 2-phenoxyethyl methacrylate, phenylthioethyl acrylate, phenylthioethyl methacrylate, 2,4,6-tribomophenyl acrylate, 2,4,6-tibromophenyl methacrylate, pentabromophenyl acrylate, pentabromophenyl methacrylate, pentachlorophenyl acrylate, pentachlorophenyl methacrylate, 2,3-dibromopropyl acrylate, 2,3-dibromopropyl methacrylate, 2-naphthyl acrylate, 2-naphthyl methacrylate, 4-methoxybenzyl acrylate, 4-methoxybenzyl methacrylate, 2-benzyloxyethyl acrylate, 2-benzyloxyethyl methacrylate, 4-chlorophenoxyethyl acrylate, 4-chlorophenoxyethyl methacrylate, 2-phenoxyethoxyethyl acrylate, 2-phenoxyethoxyethyl methacrylate, N-phenyl acrylamide, N-phenyl methacrylamide, N-benzyl acrylamide, N-benzyl methacrylamide, N,N-dibenzyl acrylamide, N,N-dibenzyl methacrylamide, N-diphenylmethyl acrylamide, N-(4-methylphenyl)methyl acrylamide, N-1-naphthyl acrylamide, N-4-nitrophenyl acrylamide, N-(2-phenylethyl) acrylamide, N-triphenylmethyl acrylamide, N-(4-hydroxyphenyl) acrylamide, N,N-methylphenyl acrylamide, N,N-phenyl phenylethyl acrylamide, N-diphenylmethyl methacrylamide, N(4-methyl phenyl)methyl methacrylamide, N-1-naphthyl methacrylamide, N-4-nitrophenyl methacrylamide, N-(2-phenylethyl) methacrylamide, N-triphenylmethyl methacrylamide, N-(4-hydroxyphenyl) methacrylamide, N,N-methylphenyl methacrylamide, N,N′

-phenyl phenylethyl methacrylamide, N-vinylcarbazole, 4-vinylpyridine, 2-vinylpyridine, styrene, 2-chlorostyrene, 3-chlorostyrene, 4-chlorostyrene, 2-bromostyrene, 3-bromostyrene, 4-bromostyrene, 2,6-dichlorostyrene, 2-iodostyrene, 3-iodostyrene, 4-iodostyrene, pentabromostyrene, 4-phenylstyrene, 1-vinylnaphthalene, 2-vinylnaphthalene, 9-vinylanthracene and 4-phenoxystyrene.

101. The method of claim 88 wherein said high refractive index monomer and said hydrophilic monomer comprise at least about 70 percent by weight of said composition.

102. The method of claim 88 wherein said high refractive index monomer and said hydrophilic monomer comprise approximately 75 percent by weight of said composition.

103. A method of using an intraocular lens manufactured from a hydrogel composition polymerized from polymerization materials including a high refractive index monomer, a hydrophilic monomer present in an amount greater than that of said high refractive index monomer, an initiator and a crosslinker, having a water content of approximately 5 to 30 percent by weight and a refractive index of approximately 1.45 or greater, comprising:

placing said intraocular lens within an eye through an incision in the cornea of an eye.

104. The method of claim 103 wherein said polymerization materials include an ultraviolet light absorbing material.

105. The method of claim 103 wherein said polymerization materials include an ultraviolet light absorbing material selected from the group consisting of beta-(4-benzotriazoyl-3-hydroxyphenoxy)ethyl acrylate, 4-(2-acryloxyethoxy)-2-hydroxybenzophenone, 4-methacryloxy-2-hydroxybenzophenone, 2-(2′

-methacryloxy-5′

-methylphenyl)benzotriazole, 2-(2′

-hydroxy-5′

-methaoryoxyethylphenyl)-2H-benzotriazole, 2-[3′

-tert-Butyl-2′

-hydroxy-5′

-(3″

-methacyloyloxypropyl) phenyl]-5-chlorobenzotriazole, 2-[3′

-tert-Butyl-5′

-(3-dimethylvinylsilylpropoxy)-2′

-hydroxyphenyl]-5-methoxybenzotriazole, 2-(3′

-Allyl-2′

-hydroxy-5′

-methylphenyl)benzotriazole, 2-[3′

-tert-Butyl-2′

-hydroxy-5′

-(3″

-methacryloyloxypropoxy)phenyl]-5-methoxybenzotriazole and 2-[3′

-tert-Butyl-2′

-hydroxy-5′

-(3″

-methacryloyloxypropoxy) phenyl]-5-chlorobenzotriazole.

106. The method of claim 103 wherein said polymerization materials include beta-(4-benzotriazoyl-3-hydroxyphenoxy)-ethyl acrylate as an ultraviolet light absorbing material.

107. The method of claim 103 wherein said initiator is selected from the group consisting of azobis(isobutyronitrile), 2,2′

-azobis(2,4-dimethylvaleronitrile), 2,2′

-azobis(methylbutyronitrile), 1,1′

-azobis(cyanocydohexane), di-t-butyl peroxide, dicumyl peroxide, t-butylcumyl peroxide, 2,5-dimethyl-2,5-bis-2-ethylhexanoylperoxy) hexane, t-butylperoxyneodecanote, t-butyl peroxy 2-ethylhexanoate, di(4-t-butyl cyclohexyl) peroxydicarbonate, t-butyl peroxypivalate, decanoyl peroxide, lauroyl peroxide, benzoyl peroxide, 2,4-pentanedione cyanocyclohexane peroxide, di(n-propyl)peroxydicarbonate, t-amyl peroxyneodecanoate and t-butyl peroxyacetate.

108. The method of claim 103 wherein said initiator is azobis(isobutyronitrile).

109. The method of claim 103 wherein said crosslinker is selected from the group consisting of ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate and poly(ethylene glycol) dimethacrylate.

110. The method of claim 103 wherein said crosslinker is ethylene glycol dimethacrylate.

111. The method of claim 103 wherein said hydrophilic monomer is a monomer represented by the formula

112. The method of claim 103 wherein said hydrophilic monomer is selected from the group consisting of 2-hydroxyethyl methacrylate, hydroxyethoxyethyl methacrylate, hydroxydiethoxyethyl methacrylate, methoxyethyl methacrylate, methoxyethoxyethyl methacrylate, methoxydiethoxyethyl methacrylate, poly(ethylene glycol) methacrylate, methoxy-poly(ethylene glycol) methacrylate, methacrylic acid, sodium methacrylate, glycerol methacrylate, hydroxypropyl methacrylate, and hydroxybutyl methacrylate.

113. The method of claim 103 wherein said hydrophilic monomer is 2-hydroxyethyl methacrylate.

114. The method of claim 103 wherein said high refractive index monomer is a monomer represented by one of the formulas

115. The method of claim 103 wherein said high refractive index monomer is selected from the group consisting of phenyl acrylate, phenyl methacrylate, benzyl acrylate, benzyl methacrylate, 2-phenylethyl acrylate, 2-phenylethyl methacrylate, 2-phenoxyethyl acrylate, 2-phenoxyethyl methacrylate, phenylthioethyl acrylate, phenythioethyl methacrylate, 2,4,6-tribromophenyl acrylate, 2,4,6-tribromophenyl methacrylate, pentabromophenyl acrylate, pentabromophenyl methacrylate, pentachlorophenyl acrylate, pentachlorophenyl methacrylate, 2,3-dibromopropyl acrylate, 2,3-dibromopropyl methacrylate, 2-naphthyl acrylate, 2-naphthyl methacrylate, 4-methoxybenzyl acrylate, 4-methoxybenzyl methacrylate, 2-benzyloxyethyl acrylate, 2-benzyloxyethyl methacrylate, 4-chlorophenoxyethyl acrylate, 4-chlorophenoxyethyl methacrylate, 2-phenoxyethoxyethyl acrylate, 2-phenoxyethoxyethyl methacrylate, N-phenyl acrylamide, N-phenyl methacrylamide, N-benzyl acrylamide, N-benzyl methacrylamide, N,N-dibenzyl acrylamide, N,N-dibenzyl methacrylamide, N-diphenylmethyl acrylamide, N-(4-methylphenyl)methyl acrylamide, N-1-naphthyl acrylamide, N-4-nitrophenyl acrylamide, N-(2-phenylethyl) acrylamide, N-triphenylmethyl acrylamide, N-(4-hydroxyphenyl) acrylamide, N,N-methylphenyl acrylamide, N,N-phenyl phenylethyl acrylamide, N-diphenylmethyl methacrylamide, N-(4-methyl phenyl)methyl methacrylamide, N-1-naphthyl methacrylamide, N-4-nitrophenyl methacrylamide, N-(2-phenylethyl) methacrylamide, N-triphenylmethyl methacrylamide, N-(4-hydroxyphenyl) methacrylamide, N,N-methylphenyl methacrylamide, N,N′

-phenyl phenylethyl methacrylamide, N-vinylcarbazole, 4-vinylpyridine, 2-vinylpyridine, styrene, 2-chlorostyrene, 3-chlorostyrene, 4-chlorostyrene, 2-bromostyrene, 3-bromostyrene, 4-bromostyrene, 2,6-dichlorostyrene, 2-iodostyrene, 3-iodostyrene, 4-iodostyrene, pentabromostyrene, 4-phenylstyrene, 1-vinylnaphthalene, 2-vinylnaphthalene, 9-vinylanthracene and 4-phenoxystyrene.

116. The method of claim 103 wherein said high refractive index monomer and said hydrophilic monomer comprise at least about 70 percent by weight of said composition.

117. The method of claim 103 wherein said high refractive index monomer and said hydrophilic monomer comprise approximately 75 percent by weight of said composition.