Contact lens made from polymers of polysiloxane and polycyclic esters of acrylic acid or methacrylic acid

• US 4,254,248 A
• Filed: 09/13/1979
• Issued: 03/03/1981
• 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: Friends, Gary D., VanBuren, Martin F.
• Primary Examiner(s): Briggs, Sr., Wilbert J.
• Application Number:
  US06/074,922
• Time in Patent Office: 537 Days
• Field of Search: 525/479, 528/26, 526/279, 526/282
• US Class Current: 526/279
• CPC Class Codes: C08F 220/1811 C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate
• CPC Class Codes: C08F 230/08 containing silicon
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

Monomeric polysiloxanes end-capped with activated unsaturated groups polymerized with a comonomer comprising a polycyclic ester of acrylic acid or methacrylic acid to form a soft contact lens is disclosed. These instant polysiloxane copolymer contact lenses have unexpectedly high tear strengths and unexpectedly high modulus of elasticity.

Claims

1. A soft, flexible, 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 polysiloxane monomer, α

,ω

terminally bonded through divalent hydrocarbon groups to polymerized, free radical polymerizably activated, unsaturated groups copolymerized with from about 20 percent by weight to about 80 percent by weight, based on the total weight of the solution, of a monomer selected from the group consisting of a polycyclic ester of acrylic acid and a polycyclic ester of methacrylic acid, forming a polymer in a crosslinked network having a tensile modulus of elasticity of at least about 200 g/mm² with a tear strength of at least about 5.0 g/mm thickness.

2. A contact lens according to claim 1 wherein the polycyclic ester monomer is a polycyclic ester of acrylic acid.

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

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

5. The contact len according to claim 4 wherein isobornyl acrylate is present in amounts from about 20 weight percent to about 80 weight percent.

6. The contact lens according to claim 1 wherein the tensile modulus of elasticity is from about 200 g/mm² to about 100,000 5/mm².

7. The contact lens according to claim 1 wherein the tear strength is from about 5.0 g/mm to about 250 g/mm thickness.

8. The contact lens according to claim 1 wherein the polysiloxane monomer is selected from the group consisting of a 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 the 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 group, a carboxylic acid 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 2 or greater and m'"'"' is 1 or greater.

9. The contact lens according to claim 8 wherein the polysiloxane monomer has the formula ##STR39## 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 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.

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

11. The contact lens according to claim 10 wherein m is a number of from about 50 to about 700.

12. The contact lens according to claim 11 which has a Shore hardness of 60 or below on the Shore hardness scale A.

13. The contact lens according to claim 12 which has a Shore hardness of 25 to 35 on the Shore hardness scale A.

14. The contact lens according to claim 9 which has an oxygen transportability of at least 2×

10^-6 cm³ /(sec. cm² atm).

15. The contact lens according to claim 9 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.

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

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

18. The contact lens according to claim 9 wherein R₁, R₂, R₃ and R₄ are selected from the group consisting of a methyl radical and a phenyl radical.

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

20. The contact lens according to claim 8 wherein the polysiloxane monomer has the formula ##STR40## 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 group, a carboxylic acid ester group represented by the formula ##STR41## wherein R'"'"'₇ is selected from the group containing from 1 to about 12 carbon atoms and a carboxylic acid amide represented by the formula ##STR42## 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 2 or greater and m'"'"' is 1 or greater.

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

22. The contact lens according to claim 20 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 60 or below on the Shore hardness scale A.

24. The contact lens according to claim 20 wherein x is a number from 2 to 3.

25. The contact lens according to claim 20 where 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-4-yl and 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 10 carbon 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 20 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.