Hydrophilic siloxane monomers and dimers for contact lens materials, and contact lenses fabricated therefrom

• US 4,711,943 A
• Filed: 04/26/1985
• Issued: 12/08/1987
• Est. Priority Date: 04/26/1985
• Status: Expired due to Term

• Current Assignee: Novartis Ag
• Original Assignee: Sola U.S.A. Inc.
• Inventors: Harvey, Thomas B. III
• Primary Examiner(s): Kulkosky, Peter F.
• Application Number:
  US06/727,501
• Time in Patent Office: 956 Days
• Field of Search: 523/107, 526/279, 556/420
• US Class Current: 526/279
• CPC Class Codes: C07F 7/0838 Compounds with one or more Si-O-Si sequences compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21
• CPC Class Codes: C08F 230/08 containing silicon
• CPC Class Codes: C08L 43/04 Homopolymers or copolymers of monomers containing silicon
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

A monomer for making a contact lens with improved oxygen permeability and stability is disclosed as having a first portion for increasing wettability and a second portion for increasing oxygen permeability. The first portion includes a side-chain functionality of the structural formula: ##STR1## and is hydrophilic. The second portion includes a siloxane moiety, and is usually hydrophobic.

Also disclosed is a cross-linking agent, a polymeric material for making contact lenses, a method for making the polymeric material, and a method for making contact lenses from the material.

Claims

1. A non-fibrous polymeric contact lens material having improved oxygen permeability and stability, said polymeric contact lens material comprising a monomer having the following structural formula:

first portion for increasing wettability, said first portion being hydrophilic and including a side-chain functionality selected from the group including the following structural formulae;

##STR51## and a second portion for increasing oxygen permeability, said second portion including a siloxane;

wherein;

said material has a water content of about 15-60%;

DK greater than or equal to about 25×

10^-10 ;

tear strength greater than or equal to about 1.0 g/mm² ; and

percent elongation greater than or equal to about 80%.

2. The contact lens material of claim 1 wherein said first portion comprises an acrylamide or a methacrylamide.

3. The contact lens material of claim 1 wherein said second portion comprises an alkyl siloxane.

4. The contact lens material of claim 2 wherein said second portion comprises an alkyl siloxane.

5. The contact lens material of claim 1 wherein said first portion comprises the following structural formula:

##STR52## wherein;

X¹ is CH₃ or H;

X² is CH₃ or H;

m is 0 or 1; and

Y is selected from the group consisting of the following structural formulae, the radical shown on the left of each formula being bonded to the carbon shown on the left of Y in the above formula;

##STR53##

6. The contact lens material of claim 1 wherein said first portion comprises the following structural formula:

##STR54## wherein X is CH₃ or H.

7. The contact lens material of claim 1 wherein said second portion comprises the following structural formula:

##STR55## wherein;

n is an integer from 1 to 6;

A¹ and A² are the same or different and are selected from lower alkyl and B groups; and

B has the following structural formula;

##STR56## wherein;

Z¹, Z² and Z³ are the same or different and are selected from the group consisting of lower alkyl, phenyl, benzyl and tri-alkylsiloxy substituents.

8. The contact lens material of claim 5 wherein said second portion comprises the following structural formula:

##STR57## wherein;

n is an integer from 1 to 6;

A¹ and A² are the same or different and are selected from lower alkyl and B groups; and

B has the following structural formula;

##STR58## wherein;

Z¹, Z² and Z³ are the same or different and are selected from the group consisting of lower alkyl, phenyl, benzyl and tri-alkylsiloxy substituents.

9. The contact lens material of claim 7 wherein:

n is 3; and

Z¹, Z² and Z³ are lower alkyl.

10. The contact lens material of claim 8 wherein:

n is 3; and

Z¹, Z² and Z³ are lower alkyl.

11. The contact lens material of claim 9 wherein Z¹, Z² and Z³ are CH₃.

12. The contact lens material of claim 10 wherein Z¹, Z² and Z³ are CH₃.

13. The contact lens material of claim 6 wherein said second portion has the following structural formula:

##STR59##

14. A contact lens formed from the contact lens material of claim 1.

15. A contact lens formed from the contact lens material of claim 5.

16. A contact lens formed from the contact lens material of claim 7.

17. A contact lens formed from the contact lens material of claim 8.

18. A contact lens formed from the contact lens material of claim 13.

19. A non-fibrous polymeric material for making a contact lens with improved oxygen permeability and stability, said contact lens material comprising a monomer having the following structural formula:

##STR60## wherein;

X¹ is CH₃ or H;

X² is CH₃ or H;

m is 0 or 1; and

Y is selected from the group consisting of the following structural formulae, the radical shown on the left of each formula being bonded to the carbon shown on the left of Y in the above formula;

##STR61## wherein;

n is an integer from 1 to 6;

A¹ and A² are the same or different and are selected from lower alkyl and B groups; and

B has the following structural formula;

##STR62## wherein;

Z¹, Z² and Z³ are the same or different and are selected from the group consisting of lower alkyl, phenyl, benzyl and tri-alkyl-siloxy substituents;

and

wherein;

said material has a water content of about 15-60%;

DK greater than or equal to about 25×

10^-10 ;

tear strength greater than or equal to about 1.0 g/mm² ; and

percent elongation greater than or equal to about 80%.

20. The contact lens material of claim 19 wherein:

m is 0;

n is 3; and

Z¹, Z² and Z³ are CH₃.

21. The contact lens material of claim 20 wherein X¹ is CH₃.

22. The contact lens material of claim 20 wherein X² is H.

23. The contact lens material of claim 21 wherein X² is H.

24. A contact lens made from the contact lens material of claim 19.

25. A non-fibrous contact lens material for making a contact lens with improved oxygen permeability and stability, said contact lens material comprising a polymer formed from at least a monomer having the following structural formula:

##STR63## wherein;

said material has a water content of about 15-60%;

DK greater than or equal to about 24×

10^-10 ;

tear strength greater than or equal to about 1.0 g/mm² ; and

percent elongation greater than or equal to about 80%.

26. A non-fibrous contact lens material for making a contact lens with improved oxygen permeability and stability, said contact lens material comprising a polymer formed from at least a monomer having the following structural formula:

##STR64## wherein;

said material has a water content of about 15-60%;

DK greater than or equal to about 25×

10^-10 ;

tear strength greater than or equal to about 1.0 g/mm² ; and

percent elongation greater than or equal to about 80%.

27. A non-fibrous contact lens material comprising the copolymerization product of:

(a) a first monomer having;

a first portion for increasing wettability, said first portion being hydrophilic and including a side-chain functionality selected from the group consisting of the following structural formulae;

##STR65## and a second portion for increasing oxygen permeability, said second portion including a siloxane;

(b) a second monomer, copolymerizable with said first monomer;

(c) a crosslinking agent; and

(d) a polymerization initiator; and

wherein;

said material has a water content of about 15-60%;

DK greater than or equal to about 25×

10^-10 ;

tear strength greater than or equal to about 1.0 g/mm² ; and

percent elongation greater than or equal to about 80%.

28. The contact lens material of claim 27 comprising the copolymerization product of:

(a) 30-100 wt/wt% of said first monomer;

(b) 0-70 wt/wt% of said second monomer;

(c) 0-10 wt/wt% of said crosslinking agent;

(d) 0-5 wt/wt% of said polymerization initiator; and

(e) 0-20 wt/wt% of a diluent.

29. The contact lens material of claim 28 comprising the copolymerization product of:

(a) 35-45 wt/wt% of said first monomer;

(b) 45-55 wt/wt% of said second monomer;

(c) 0-10 wt/wt% of said crosslinking agent;

(d) 0-5 wt/wt% of said polymerization initiator; and

(e) 0-10 wt/wt% of a diluent.

30. The contact lens material of claim 28 comprising the copolymerization product of:

(a) 38-44 wt/wt% of said first monomer;

(b) 47-52 wt/wt% of said second monomer;

(c) 3-8 wt/wt% of said crosslinking agent;

(d) 0-1 wt/wt% of said polymerization initiator; and

(e) 0-7 wt/wt% of a diluent.

31. The contact lens material of claim 28 comprising the copolymerization product of:

(a) 41 wt/wt% of said first monomer;

(b) 49 wt/wt% of said second monomer;

(c) 5.5 wt/wt% of said crosslinking agent;

(d) 0.5 wt/wt% of said polymerization initiator; and

(e) 4.0 wt/wt% of said diluent.

32. The contact lens material of claim 28 wherein said first monomer is N-[tris(trimethylsiloxy)silylpropyl]methacrylamide.

33. The contact lens material of claim 29 wherein said first monomer is N-[tris(trimethylsiloxy)silylpropyl]methacrylamide.

34. The contact lens material of claim 32 wherein said first monomer is N-[tris(trimethylsiloxy)silylpropyl]methacrylamide.

35. The contact lens material of claim 28 wherein said crosslinking agent is 1,3-Bis(methacrylamidopropyl)-1,1,3,3-tetrakis(trimethylsiloxy)disiloxane.

36. The contact lens material of claim 29 wherein said crosslinking agent is 1,3-Bis(methacrylamidopropyl)-1,1,3,3-tetrakis(trimethylsiloxy)disiloxane.

37. The contact lens material of claim 32 wherein said crosslinking agent is 1,3-Bis(methacrylamidopropyl)-1,1,3,3-tetrakis(trimethylsiloxy)disiloxane.

38. The contact lens material of claim 33 wherein said crosslinking agent is 1,3-Bis(methacrylamidopropyl)-1,1,3,3-tetrakis(trimethylsiloxy)disiloxane.

39. The contact lens material of claim 34 wherein said crosslinking agent is 1,3-Bis(methacrylamidopropyl)-1,1,3,3-tetrakis(trimethylsiloxy)disiloxane.

40. The contact lens material of claim 35 wherein said crosslinking agent is 1,3-Bis(methacrylamidopropyl)-1,1,3,3-tetrakis(trimethylsiloxy)disiloxane.

41. The contact lens material of claim 28 wherein said first monomer has the following structural formula:

##STR66## wherein;

X¹ is CH₃ or H;

X² is CH₃ or H;

m is 0 or 1;

n is an integer from 1 to 6;

Y is selected from the group consisting of the following structural formulae, the radical shown on the left of each formula being bonded to the carbon shown on the left of Y in the above formula;

##STR67## A¹ and A² are the same or different and are selected from lower alkyl and B groups; and

B has the following structural formula;

##STR68## wherein;

Z¹, Z² and Z³ are the same or different and are selected from the group consisting of lower alkyl, phenyl, benzyl and tri-alkylsiloxy substituents.

42. The contact lens material of claim 41 wherein:

m is 0;

n is 3; and

Z¹, Z² and Z³ are CH₃.

43. The contact lens material of claim 42 wherein X¹ is CH₃.

44. The contact lens material of claim 42 wherein X² is H.

45. The contact lens material of claim 44 wherein X¹ is CH₃.

46. The contact lens material of claim 32 wherein said crosslinking agent is ethyleneglycoldimethacrylate or tetraethyleneglycoldimethacrylate.

47. The contact lens material of claim 28 wherein said second monomer is selected from the group consisting of:

methyl methacrylate, hydroxyethyl methacrylate, glyceryl methacrylate, N,N-dimethylacrylamide, N-Vinyl pyrrolidone, α

-Methylglucoside-6-methacrylate, and methacrylic acid.

48. The contact lens material of claim 27 wherein said crosslinking agent comprises the following structural formula:

##STR69## wherein;

X¹ is CH₃ or H;

X² is CH₃ or H;

m is 0 or 1;

n is an integer from 1 to 6;

A¹ to A³ are the same or different and are selected from lower alkyl, phenyl, benzyl, and tri-substituted-siloxy; and

Y is selected from the group consisting of the following structural formulae, the radical shown on the left of each formula being bonded to a carbon bearing an X¹ substituent in the above formula;

##STR70##

49. The contact lens material of claim 41 wherein said crosslinking agent comprises the following structural formula:

##STR71## wherein;

X¹ is CH₃ or H;

X² is CH₃ or H;

m is 0 or 1;

n is an integer from 1 to 6;

A¹ to A³ are the same or different and are selected from lower alkyl, phenyl, benzyl, and tri-substituted-siloxy; and

Y is selected from the group consisting of the following structural formulae, the radical shown on the left of each formula being bonded to a carbon bearing an X¹ substituent in the above formula;

##STR72##

50. A non-fibrous contact lens material having improved oxygen permeability and stability, said contact lens material comprising a polymer formed from at least a monomer having:

a first portion for increasing wettability, said first portion being hydrophilic and including a side-chain functionality selected from the group including the following structural formulae;

##STR73## and a second portion for increasing oxygen permeability, said second portion including a siloxane;

wherein;

said material has a water content of about 15-60%;

DK greater than or equal to about 25×

10^-10 ;

tear strength greater than or equal to about 1.0 g/mm² ; and

percent elongation greater than or equal to about 80%.

51. The contact lens material of claim 50 wherein said first portion comprises an acrylamide or a methacrylamide.

52. The contact lens material of claim 50 wherein said second portion comprises an alkyl silyl siloxane.

53. The contact lens material of claim 51 wherein said second portion comprises an alkyl silyl siloxane.

54. The contact lens material of claim 50 wherein said first portion comprises the following structural formula:

##STR74## wherein;

X¹ is CH₃ or H;

X² is CH₃ or H;

m is 0 or 1; and

Y is selected from the group consisting of the following structural formulae, the radical shown on the left of each formula being bonded to the carbon shown on the left of Y in the above formula;

##STR75##

55. The contact lens material of claim 50 wherein said first portion comprises the following structural formula:

##STR76## wherein X is CH₃ or H.

56. The contact lens material of claim 50 wherein said second portion comprises the following structural formula:

##STR77## wherein;

n is an integer from 1 to 6;

A¹ and A² are the same or different and are selected from lower alkyl and B groups; and

B has the following structural formula;

##STR78## wherein;

Z¹, Z² and Z³ are the same or different and are selected from the group consisting of lower alkyl, phenyl, benzyl and tri-alkylsiloxy substituents.

57. The contact lens material of claim 54 wherein said second portion comprises the following structural formula:

##STR79## wherein;

n is an integer from 1 to 6;

A¹ and A² are the same or different and are selected from lower alkyl and B groups; and

B has the following structural formula;

##STR80## wherein;

Z¹, Z² and Z³ are the same or different and are selected from the group consisting of lower alkyl, phenyl, benzyl and tri-alkylsiloxy substituents.

58. The contact lens material of claim 56 wherein:

n is 3; and

Z¹, Z² and Z³ are lower alkyl.

59. The contact lens material of claim 57 wherein:

n is 3; and

Z¹, Z² and Z³ are lower alkyl.

60. The contact lens material of claim 58 wherein Z¹, Z² and Z³ are CH₃.

61. The contact lens material of claim 59 wherein Z¹, Z² and Z³ are CH₃.

62. The contact lens material of claim 55 wherein said second portion has the following structural formula:

##STR81##

63. A contact lens formed from the contact lens material of claim 50.

64. A contact lens formed from the contact lens material of claim 54.

65. A contact lens formed from the contact lens material of claim 56.

66. A contact lens formed from the contact lens material of claim 57.

67. A contact lens formed from the contact lens material of claim 62.

68. A non-fibrous material for working a contact lens with improved oxygen permeability and stability, said contact lens material comprising a polymer formed from at least a monomer having the following structural formula:

##STR82## wherein;

X¹ is CH₃ or H;

X² is CH₃ or H;

m is 0 or 1; and

Y is selected from the group consisting of the following structural formulae, the radical shown on the left of each formula being bonded to the carbon shown on the left of Y in the above formula, ##STR83## wherein;

n is an integer from 1 to 6;

A¹ and A² are the same or different and are selected from lower alkyl and B groups; and

B has the following structural formula;

##STR84## wherein;

Z¹, Z² and Z³ are the same or different and are selected from the group consisting of lower alkyl, phenyl, benzyl and tri-alkyl-siloxy substituents; and

wherein;

said material has a water content of about 15-60%;

DK greater than or equal to about 25×

10^-10 ;

tear strength greater than or equal to about 1.0 g/mm² ; and

percent elongation greater than or equal to about 80%.

69. The contact lens material of claim 68 wherein:

m is 0;

n is 3; and

Z¹, Z² and Z³ are CH₃.

70. The contact lens material of claim 69 wherein X¹ is CH₃.

71. The contact lens material of claim 69 wherein X² is H.

72. The contact lens material of claim 70 wherein X² is H.

73. A contact lens made from the contact lens material of claim 69.