Polysiloxane composition and contact lens

• US 4,153,641 A
• Filed: 02/21/1978
• Issued: 05/08/1979
• Est. Priority Date: 07/25/1977
• Status: Expired due to Term

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Su, Kai C., Deichert, William G., VAN Buren, Martin F.
• Primary Examiner(s): Marquis, Melvyn I.
• Application Number:
  US05/878,831
• Time in Patent Office: 441 Days
• Field of Search: 351/160, 260/46.56 A, 260/448.2 Q, 260/448.2 B, 260/827, 260/46.5 Y, 260/46.5 H, 26/279, 264/1, 264/2, 528/24, 528/26, 528/27, 528/32, 528/37
• US Class Current: 526/264
• 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 51/085 on to polysiloxanes
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: C08L 83/14 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms C08L83/10 takes precedence
• CPC Class Codes: G02B 1/04 made of organic materials, e.g. plastics G02B1/08 takes precedence
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

Monomeric polysiloxanes end-capped with activated unsaturated groups and polymers and copolymers thereof are disclosed herein for use as contact lenses with improved properties, such as, oxygen transportability, hydrolytic stability, biological inertness, transparency and improved strength without the use of fillers. The polymer composition comprises a poly(organosiloxane) α, ω terminally bonded through a divalent hydrocarbon group to a polymerized activated unsaturated group. Contact lenses made therefrom can be, as commonly referred to, "hard" or "soft". This hardness or softness is a function of the comonomer or the molecular weight of the monomers. Preferable the contact lenses are "soft".

The copolymer compositions of the instant invention comprise the polymerization product of the polysiloxane monomers and monomer or monomers containing an activated vinyl group. These polymers are employed to make optical products, e.g. contact lenses, intraocular implants, etc.

Claims

1. A fillerless, hydrolytically stable, biologically inert, transparent, contact lens with the capability of transporting oxygen sufficiently to meet the requirements of the human cornea comprising a poly(organosiloxane) monomer α

,ω

terminally bonded through divalent hydrocarbon groups to polymerized, free radical polymerizably activated, unsaturated groups forming a polymer in a cross-linked network.

2. The contact lens according to claim 1 wherein the poly(organosiloxane) monomer has the formula:

##STR22## wherein A is an activated unsaturated group, R is a divalent hydrocarbon radical having from 1 to about 22 carbon atoms, R₁, R₂, R₃ and R₄ can be the same or different and is selected from the group consisting of a monovalent hydrocarbon radical or a halogen substituted monovalent hydrocarbon radical each having from 1 to 12 carbon atoms and m is 0 or greater.

3. The contact lens according to claim 2 wherein A is selected from the group consisting of 2-cyanoacryloxy, acrylonitryl, acrylamido, acryloxy, methacryloxy, styryl, N-vinyl-2-pyrrolidinone-3-yl, N-vinyl-2-pyrrolidinone-4-yl and N-vinyl-2-pyrrolidinone-5-yl and R is an alkylene radical and R₁, R₂, R₃ and R₄ is an alkyl radical having from 1 to 10 carbon atoms.

4. The contact lens according to claim 3 wherein m is a number from 0 to about 200.

5. The contact lens according to claim 4 wherein m is a number from 0 to about 50.

6. The contact lens according to claim 5 wherein m is a number from 0 to about 25.

7. The contact lens according to claim 6 wherein the contact lens has a Shore hardness of above 60 on the Shore hardness scale A.

8. The contact lens according to claim 1 wherein the contact lens has a Shore hardness of 60 or below on the Shore hardness scale A.

9. The contact lens according to claim 8 which has a Shore hardness of 25 to 35 on the Shore hardness scale A.

10. The contact lens according to claim 1 which has an oxygen transportability of at least 2×

10^-6 cm³ / (sec. cm² atm).

11. A fillerless, hydrolytically stable, biologically inert, transparent, contact lens with the capability of transporting oxygen sufficiently to meet the requirements of the human cornea comprising a poly(organosiloxane) monomer α

,ω

terminally bonded through divalent hydrocarbon groups to polymerized, free radical polymerizably activated, unsaturated groups copolymerized with one or more monomers selected from the group consisting of a lower ester of acrylic and methacrylic acid, styryls, and N-vinyl pyrrolidinone forming a copolymer in a crosslinked network.

12. The contact lens according to claim 11 wherein the monomers are selected from the group consisting of styrene and N-vinyl pyrrolidone.

13. The contact lens according to claim 11 wherein the monomer is selected from the group consisting of allyl methacrylate, butoxyethylmethacrylate, cyclohexyl methacrylate, ethyl methacrylate, methylmethacrylate, ethyl hexyl acrylate, n-butyl acrylate, butyl acrylate and N-vinyl pyrrolidinone.

14. A fillerless, flexible, hydrolytically stable, biologically inert, transparent, resilient, soft, polymeric contact lens with the capability of transporting oxygen sufficiently to meet the requirements of the human cornea comprising a poly(organosiloxane) monomer α

,ω

terminally bonded through divalent hydrocarbon groups to polymerized, free radical polymerizably activated, unsaturated groups forming a polymer in a crosslinked network.

15. The contact lens according to claim 14 wherein the contact lens has a Shore hardness of 60 or below on the Shore hardness scale A.

16. The contact lens according to claim 15 which has a Shore hardness of 25 to 35 on the Shore hardness acale A.

17. The contact lens according to claim 14 wherein the contact lens has a tensile modulus of elasticity of about 400 g/mm/mm² or less.

18. The contact lens according to claim 14 wherein the oxygen transportability is at least 2×

10^-6 cm³ / (sec. cm² atm).

19. The contact lens according to claim 14 wherein the lens is made by spin casting.

20. The contact lens according to claim 14 wherein the poly(organosiloxane) monomer has the formula:

##STR23## wherein A is an activated unsaturated group, R is a divalent hydrocarbon radical having from 1 to about 22 carbon atoms, R₁, R₂, R₃ and R₄ can be the same or different and is selected from the group consisting of a monovalent hydrocarbon radical or a halogen substituted monovalent hydrocarbon radical each having from 1 to 12 carbon atoms and m is 50 or greater.

21. The contact lens according to claim 20 wherein m is a number of from about 50 to about 800.

22. The contact lens according to claim 21 wherein A is selected from the group consisting of 2-cyanoacryloxy, acrylonitryl, acrylamido, acryloxy, methacryloxy, styryl, N-vinyl-2-pyrrolidinone-3-yl, N-vinyl-2-pyrrolidinone-4-yl and N-vinyl-2-pyrrolidinone-5-yl and R is an alkylene radical and R₁, R₂, R₃ and R₄ is an alkyl radical having from 1 to 10 carbon atoms.

23. The contact lens according to claim 22 wherein the alkylene radical has from about 1 to about 4 carbon atoms.

24. The contact lens according to claim 23 wherein the alkylene radical has from about 3 to about 4 carbon atoms.

25. The contact lens according to claim 24 wherein R₁, R₂, R₃ and R₄ are selected from the group consisting of a methyl radical and a phenyl radical.

26. The contact lens according to claim 25 wherein R₁, R₂, R₃ and R₄ are methyl radicals.

27. A fillerless, flexible, hydrolytically stable, biologically inert, transparent, resilient, soft, polymeric contact lens with the capability of transporting oxygen sufficiently to meet the requirements of the human cornea comprising a poly(organosiloxane)monomer α

,ω

terminally bonded through divalent hydrocarbon groups to polymerized, free radical polymerizably activated, unsaturated groups copolymerized with one or more monomers selected from the group consisting of a lower ester of acrylic and methacrylic acid, styryls, and N-vinyl pyrrolidone forming a copolymer in a crosslinked network.

28. The contact lens according to claim 27 wherein the monomers are selected from the group consisting of styrene and N-vinyl pyrrolidone.

29. The contact lens according to claim 27 wherein the monomer is selected from the group consisting of allyl methacrylate, butoxyethylmethacrylate, cyclohexyl methacrylate, ethyl methacrylate, methylmethacrylate, ethyl hexyl acrylate, n-butyl acrylate, butyl acrylate and N-vinyl pyrrolidone.