Polysiloxane/acrylic acid/polcyclic esters of methacrylic acid polymer contact lens

• US 4,276,402 A
• Filed: 09/13/1979
• Issued: 06/30/1981
• Est. Priority Date: 09/13/1979
• Status: Expired due to Term

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Chromecek, Richard C., Deichert, William G., VanBuren, Martin F., Falcetta, Joseph J.
• Primary Examiner(s): Marquis, Melvyn I.
• Application Number:
  US06/075,365
• Time in Patent Office: 656 Days
• Field of Search: 526/279, 526/264, 526/270, 528/23, 528/24, 528/32, 528/33, 528/26, 351/160 R, 351/160 H, 204/159.13, 204/159.23, 204/159.24, 556/416, 556/417, 556/418, 556/419, 556/440
• US Class Current: 526/264
• CPC Class Codes: C08F 283/124 on to polysiloxanes having carbon-to-carbon double bonds
• CPC Class Codes: C08G 77/50 by carbon linkages C08G77/485 takes precedence
• CPC Class Codes: C08L 43/04 Homopolymers or copolymers of monomers containing silicon

Abstract

Monomeric polysiloxanes end-capped with activated unsaturated groups polymerized with acrylic acid and a comonomer comprising a polycyclic ester of acrylic acid or methacrylic acid to form a hydrophilic, water absorbing contact lens is disclosed. These polysiloxane polymer contact lenses are unexpectedly capable upon hydration of retaining from 1 percent to about 99 percent by weight of water, based upon the total weight of the dry, i.e., unhydrated polymer.

Claims

1. A soft, hydrophilic, water absorbing, flexible, fillerless, hydrolytically stable, biologically inert contact lens with the capability of transporting oxygen sufficiently to meet the requirements of the human cornea made from a polymer comprising polymerizing a polysiloxane monomer α

,ω

terminally bonded through divalent hydrocarbon groups to polymerizable, free radical polymerizably activated, unsaturated groups with from 1.0 weight percent to about 30.0 weight percent based on the total weight of the polymer of acrylic acid and 5.0 weight percent of about 50.0 weight percent based on the total weight of the polymer of a material selected from the group of a polycyclic ester of acrylic acid and a polycyclic ester of methacrylic acid forming a polymer in a crosslinked network, said polymer capable upon saturation with water of retaining from about 1 percent by weight to about 99 percent by weight, based on the total weight of the dry polymer, of water.

2. The contact lens according to claim 1 wherein the polycyclic ester of acrylic acid is selected from the group consisting of isobornyl acrylate, adamantanyl acrylate, dicyclopentadienyl acrylate and isopinocamphyl acrylate.

3. The contact lens according to claim 2 wherein the polycyclic ester of acrylic acid is isobornyl acrylate.

4. The contact lens according to claim 1 wherein acrylic acid is present in amounts from about 5.0 weight percent to about 15.0 weight percent.

5. The contact lens according to claim 1 wherein the polycyclic ester of acrylic acid or methacrylic acid is present in amounts from about 10.0 weight percent to about 40.0 weight percent.

6. The contact lens according to claim 1 wherein the tensile modulus of elasticity is from about 50 g/mm² to about 8000 g/mm².

7. The contact lens according to claim 1 wherein the lens is substantially transparent.

8. The contact lens according to claim 1 wherein the polysiloxane monomer is selected from the group consisting of a poly(organosiloxane) monomer having the formula ##STR35## 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 and a polyparaffinpolysiloxane monomer having the formula ##STR36## wherein A₁ is an activated unsaturated group;

R'"'"' is a divalent hydrocarbon radical having from 1 to about 22 carbon atoms;

R'"'"'₁, R'"'"'₂, R'"'"'₃ and R'"'"'₄ can be the same or different and are selected from the group consisting of a monovalent hydrocarbon radical having from 1 to about 12 carbon atoms and a halogen substituted monovalent hydrocarbon radical having from 1 to about 12 carbon atoms;

R'"'"'₅ and R'"'"'₆ can be the same or different and are selected from the group consisting of hydrogen, a hydrocarbon radical containing from 1 to about 12 carbon atoms, a carboxylic acid ester group represented by the formula ##STR37## wherein R'"'"'₇ is selected from the group consisting of a hydrocarbon group containing from 1 to about 12 carbon atoms and a carboxylic acid amide represented by the formula ##STR38## wherein R'"'"'₈ and R'"'"'₉ can be the same or different and each is selected from the group consisting of hydrogen and a hydrocarbon group containing from 1 to about 12 carbon atoms;

x is 12 or greater and m'"'"' is 1 or greater.

9. The contact lens according to claim 8 wherein m is a number from 50 to about 800.

10. The contact lens according to claim 9 wherein m is a number of from about 50 to about 200.

11. The contact lens according to claim 10 which has a Shore hardness of 80 or below on the Shore hardness scale A.

12. The contact lens according to claim 11 which has a Shore hardness of 45 to 55 on the Shore hardness scale A.

13. The contact lens according to claim 8 which has an oxygen transportability of at least 2×

10^-6 cm³ /(sec.cm² atm.).

14. The contact lens according to claim 8 wherein A is selected from the group consisting of 2-cyanoacryloxy, acrylonitryl, acrylamido, acryloxy, methacryloxy, styryl, N-vinyl-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 are alkyl radicals having from 1 to 10 carbon atoms.

15. The contact lens according to claim 14 wherein the alkylene radical has from about 1 to about 4 carbon atoms.

17. The contact lens according to claim 8 wherein R₁, R₂, R₃ and R₄ are selected from the group consisting of a methyl radical and a phenyl radical.

18. The contact lens according to claim 17 wherein R₁, R₂, R₃ and R₄ are methyl radicals.

19. The contact lens according to claim 8 wherein m'"'"' is a number of from 1 to about 800.

20. The contact lens according to claim 19 wherein m'"'"' is a number from about 20 to 500.

21. The contact lens according to claim 20 wherein m'"'"' is a number of from about 20 to about 200.

22. The contact lens according to claim 8 wherein the oxygen transportability is at least 2×

10^-6 cm³ /(sec.cm² atm.).

23. The contact lens according to claim 22 which has a Shore hardness of 80 or below on the Shore hardness scale A.

24. The contact lens according to claim 8 wherein x is a number from 2 to 3.

25. The contact lens according to claim 8 wherein A₁ is selected from the group consisting of 2-cyanoacryloxy, acrylonitryl, acrylamido, acryloxy, methacryloxy, styryl, N-vinyl-2-pyrrolidinone-3-yl, N-vinyl-2-pyrrolidinone-5-yl and R'"'"' is an alkylene radical and R'"'"'₁, R'"'"'₂, R'"'"'₃ and R'"'"'₄ are alkyl radicals having from 1 to 10carbon atoms.

26. The contact lens according to claim 25 wherein the alkylene radical has from about 1 to about 4 carbon atoms.

27. The contact lens according to claim 26 wherein the alkylene radical has from about 3 to about 4 carbon atoms.

28. The contact lens according to claim 8 wherein R'"'"'₁, R'"'"'₂, R'"'"'₃ and R'"'"'₄ are selected from the group consisting of a methyl radical and a phenyl radical.

29. The contact lens according to claim 28 wherein R'"'"'₁, R'"'"'₂, R'"'"'₃ and R'"'"'₄ are methyl radicals.

30. The contact lens according to claim 29 wherein R'"'"'₅ and R'"'"'₆ are selected from the group consisting of hydrogen and methyl.

31. The contact lens according to claim 30 wherein x is a number from 2 to 3.

16. The contact lens according to claim 16 wherein the alkylene radical has from about 3 to about 4 carbon atoms.