Polysiloxane shaped article for use in biomedical applications

• US 4,189,546 A
• Filed: 12/05/1978
• Issued: 02/19/1980
• 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: Deichert, William G., Su, Kai C., van Buren, Martin F.
• Primary Examiner(s): Marquis, Melvyn I.
• Application Number:
  US05/964,761
• Time in Patent Office: 441 Days
• Field of Search: 3/1.4, 3/1, 3/36, 32/1, 128/130, 128/348, 128/349 R, 128/350 R, 128/351, 128/DIG. 21, 128/260, 351/160 H, 526/279, 528/32, 528/33, 528/24, 528/12, 528/37, 528/42, 528/26, 528/27
• US Class Current: 528/26
• 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 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
• CPC Class Codes: Y10S 128/21 Silicone

Abstract

Monomeric polysiloxanes end-capped with activated unsaturated groups and polymers and copolymers thereof are disclosed herein for use as contact lenses and biomedical devices 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) monomer α,ω terminally bonded through divalent hydrocarbon groups to polymerized free radical polymerizably activated unsaturated groups. Contact lenses and biomedical devices i.e. shaped article for use in biomedical applications made therefrom can be "hard" or "soft". This hardness or softness is a function of the comonomer or the molecular weight of the monomers. Preferably the contact lenses and biomedical devices 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 biomedical devices and optical products, e.g. contact lenses, intraocular implants, etc.

Claims

1. A fillerless, hydrolytically stable, biologically inert, transparent, oxygen transporting, polymeric, shaped article for use in biomedical applications other than as contact lenses comprising a poly(organosiloxane) monomer α

,ω

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

2. The polymeric, shaped article for use in biomedical applications 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 shaped article for use in biomedical applications 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 shaped article for use in biomedical applications according to claim 3 wherein m is a number of from 0 to about 200.

5. The shaped article for use in biomedical applications according to claim 4 wherein m is a number from 0 to about 50.

6. The shaped article for use in biomedical applications according to claim 5 wherein m is a number from 0 to abot 25.

7. A fillerless, hydrolytically stable, biologically inert, transparent, oxygen transporting, polymeric shaped article for use in biomedical applications other than as contact lenses 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 cross-linked network.

8. The shaped article for use in biomedical applications according to claim 7 wherein the monomers are selected from the group consisting of styrene and N-vinyl pyrrolidone.

9. The shaped article for use in biomedical applications according to claim 7 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.

10. A fillerless, flexible, hydrolytically stable, biologically inert, transparent, resilient, soft, oxygen transporting, polymeric, shaped article for use in biomedical applications other than as contact lenses comprising a poly (organosiloxane) monomer α

,ω

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

11. The shaped article for use in biomedical applications according to claim 10 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.

12. The shaped article for use in biomedical applications according to claim 11 wherein m is a number of from abot 50 to abot 800.

13. The shaped article for use in biomedical applications according to claim 12 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.

14. The shaped article for use in biomedical applications according to claim 13 wherein the alkylene adical has from about 1 to about 4 carbon atoms.

15. The shaped article for use in biomedical applications according to claim 14 wherein the alkylene radical has from about 3 to abot 4 carbon atoms.

16. The shaped article for use in biomedical applications according to claim 15 wherein R₁, R₂, R₃ and R₄ are selected from the group consisting of a methyl radical and a phenyl radical.

17. The shaped article for use in biomedical applications according to claim 16 wherein R₁, R₂, R₃ and R₄ are methyl radicals.

18. The shaped article for use in biomedical applications according to claim 10 wherein the contact lens comprises a poly(organosiloxane) terminally bonded through a divalent hydrocarbon group to an activated unsaturated group 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.

19. The shaped article for use in biomedical applications according to claim 18 wherein the monomers are selected from the group consisting of styrene and N-vinyl pyrrolidone.

20. A fillerless, flexible, hydrolytically stable, biologically inert, transparent, resilient, soft, oxygen transporting, polymeric, shaped article for use in biomedical applications other than as contact lenses comprising a poly (organosiloxane) monomer α

,ω

terminally bonded through divalent hydrocarbon groups to polymerized, free radical polymerizably activated, unsaturated grops 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.

21. The shaped article for use in biomedical applications according to claim 20 wherein the monomers are selected from the group consisting of styrene and N-vinyl pyrrolidone.

22. The shaped article for use in biomedical applications according to claim 20 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.