Silicone-containing contact lens material and contact lenses made thereof

• US 4,463,149 A
• Filed: 03/29/1982
• Issued: 07/31/1984
• Est. Priority Date: 03/29/1982
• Status: Expired due to Term

• Current Assignee: B&L International Holdings Corp.
• Original Assignee: Polymer Technology Group, Inc. (DSM-Firmenich AG)
• Inventors: Ellis, Edward J.
• Primary Examiner(s): Schofer, Joseph L.
• Assistant Examiner(s): Reddick, J. M.
• Application Number:
  US06/363,073
• Time in Patent Office: 855 Days
• Field of Search: 526/279, 523/106, 523/107
• 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 283/124 on to polysiloxanes having carbon-to-carbon double bonds
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: C08L 43/04 Homopolymers or copolymers of monomers containing silicon
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

According to the invention contact lenses are formed of polymerizable substituted alkyl and aryl siloxanes having one or more unsaturated, polymerizable groups. These compounds preferably contain substituted acetoxy or carbomethoxy groups which confer inherent wettability and high polarity. Novel organosiloxanes are provided particularly adaptable for use in forming contact lenses by themselves or copolymerized with other monomeric materials to form useful polymeric materials for contact lenses.

Claims

1. A contact lens material formed of a siloxane containing one or more unsaturated polymerizable groups for use in contact lens having high oxygen permeability, dimensional stability, inherent wettability, high light transmission, durability, biocompatibility, non-hydrating, chemical stability, and high resistance to proteinaceous accumulation as well as being scratch resistant having the following formula:

##STR4## wherein;

X is selected from the group consisting essentially of unsaturated polymerizable methacrylate, acrylate, hydrogen or "Z" groups and mixtures thereof,

R is selected from the group consisting essentially of alkylene, cycloalkylene groups having from 1 to about 10 carbon atoms, arylene groups and mixtures thereof,

a is an integer from 0 to about 10 where each "a" may be the same or different,

n is an integer from 0 to about 10,

Z groups are selected from the group consisting essentially of acetoxy, carbomethoxy, glycidoxy, glyceryl, and carboxy with at least one "X" being a "Z" group.

2. A contact lens material in accordance with claim 1 wherein said siloxane is 1,3-bis(γ

-methacryloxypropyl-1,1,3,3-tetra(3-acetoxypropyldimethylsiloxy)disiloxane.

3. A contact lens material in accordance with claim 1 wherein said siloxane is γ

-methacryloxypropyl-tris(4-acetoxyphenyldimethylsiloxy)silane.

4. A contact lens material in accordance with claim 1 wherein said siloxane is γ

-methacryloxypropyl-tris(2-carboxyethyldimethylsiloxy)silane.

5. A contact lens material in accordance with claim 1 wherein said siloxane is γ

-methacryloxypropyl-tris(2-acetoxyethyldimethylsiloxy)silane.

6. A contact lens material in accordance with claim 1 wherein said siloxane is 1-γ

-methacryloxymethyl-3-(3-acetoxypropyl)-1,1,3,3-tetramethyldisiloxane.

7. A contact lens material in accordance with claim 1 wherein said siloxane is γ

-methacryloxypropyl-bis(trimethylsiloxy)-(3-acetoxypropyldimethylsiloxy)silane.

8. A contact lens material in accordance with claim 1 wherein said siloxane is γ

-methacryloxypropyl-bis(trimethylsiloxy)-(3-carbomethoxypropyldimethylsiloxy)silane.

9. A contact lens material in accordance with claim 1 wherein said siloxane is γ

-methacryloxypropyl-bis(trimethylsiloxy)-(3-hydroxypropyldimethylsiloxy)silane.

10. A contact lens material in accordance with claim 1 wherein said siloxane is γ

-methacryloxypropyl-bis(trimethylsiloxy)-(3-carboxypropyldimethylsiloxy)silane.

11. A contact lens material in accordance with claim 1 wherein said siloxane is γ

-methacryloxypropyl-bis(3-acetoxypropyldimethylsiloxy)-(trimethylsiloxy)silane.

12. A contact lens material in accordance with claim 1 wherein said siloxane is γ

-methacryloxypropyl-bis(3-carbomethoxypropyldimethylsiloxy)-(trimethylsiloxy)silane.

13. A contact lens material in accordance with claim 1 wherein said siloxane is γ

-methacryloxypropyl-bis(3-hydroxypropyldimethylsiloxy)-(trimethylsiloxy)silane.

14. A contact lens material in accordance with claim 1 wherein said siloxane is γ

-methacryloxypropyl-bis(3-carboxypropyldimethylsiloxy)-(trimethylsiloxy)silane.

15. A contact lens material in accordance with claim 1 wherein said siloxane is γ

-methacryloxypropyl-tris(3-acetoxypropyldimethylsiloxy)silane.

16. A contact lens material in accordance with claim 1 wherein said siloxane is γ

-methacryloxypropyl-tris(3-carbomethoxypropyldimethylsiloxy)silane.

17. A contact lens material in accordance with claim 1 wherein said siloxane is γ

-methacryloxypropyl-tris(3-hydroxypropyldimethylsiloxy)silane.

18. A contact lens material in accordance with claim 1 wherein said siloxane is γ

-methacryloxypropyl-bis(pentamethyldisiloxanyl)-(3-acetoxypropyldimethylsiloxy)silane.

19. A contact lens material in accordance with claim 1 wherein said siloxane is γ

-methacryloxypropyl-bis(pentamethyldisiloxyanyl)-(3-carbomethoxypropyldimethylsiloxy)silane.

20. A contact lens material in accordance with claim 1 wherein said siloxane is γ

-methacryloxypropyl-bis(pentamethyldisiloxanyl)-(3-hydroxypropyldimethylsiloxy)silane.

21. A contact lens material in accordance with claim 1 wherein said siloxane is γ

-methacryloxypropyl-bis(pentamethyldisiloxanyl)-(3-carboxypropyldimethylsiloxy)silane.

22. A contact lens material in accordance with claim 1 wherein said siloxane is 1-(γ

-methacryloxypropyl)-3-(3-acetoxypropyl)-tetra(trimethylsiloxy)disiloxane.

23. A contact lens material in accordance with claim 1 wherein said siloxane is 1-(γ

-methacryloxypropyl)-3-(3-carbomethoxypropyl)-tetra(trimethylsiloxy)disiloxane.

24. A contact lens material in accordance with claim 1 wherein said siloxane is 1-(γ

-methacryloxypropyl)-3-(3-hydroxypropyl)-tetra(trimethylsiloxy)disiloxane.

25. A contact lens material in accordance with claim 1 wherein said siloxane is 1-(γ

-methacryloxypropyl)-3-(3-carboxypropyl)-tetra(trimethylsiloxy)disiloxane.

26. A contact lens formed of a siloxane containing one or more unsaturated polymerizable groups having the following formula:

##STR5## wherein;

X is selected from the group consisting essentially of unsaturated polymerizable methacrylate, acrylate, hydrogen or "Z" groups and mixtures thereof,

R is selected from the group consisting essentially of alkylene, cycloalkylene groups having from 1 to about 10 carbon atoms, arylene groups and mixtures thereof,

a is an integer from 0 to about 10 where each "a" may be the same or different,

n is an integer from 0 to about 10,

Z groups are selected from the group consisting essentially of acetoxy, carbomethoxy, glycidoxy, glyceryl, and carboxy with at least one "X" being a "Z" group.

27. A contact lens in accordance with claim 26 wherein said siloxane is copolymerized with a hardening agent.

28. A contact lens in accordance with claim 26 wherein said siloxane is copolymerized with a wetting agent.

29. A contact lens in accordance with claim 28 and further including a hardening agent.

30. A contact lens in accordance with claim 29 wherein said hardening agent is selected from the group consisting of acrylic, methacrylic acid itaconic acid derivatives including esters of a C₁ -C₂₀ monohydric or polyhydric alkanol, phenol and an acid selected from the class consisting essentially of acrylic and methacrylic acid, itaconate mono and diester.

31. A contact lens in accordance with claim 30 wherein said wetting agent is selected from the group consisting of neutral monomers, hydrophilic cationic monomers and hydrophilic anionic monomers.