Polysiloxane with cycloalkyl modifier composition and biomedical devices

• US 4,327,203 A
• Filed: 02/26/1981
• Issued: 04/27/1982
• Est. Priority Date: 02/26/1981
• Status: Expired due to Fees

• Current Assignee: Kbausch & LOMB Incorporated
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Friends, Gary D., Melpolder, John B., Deichert, William G., Park, Joon S.
• Primary Examiner(s): Marquis, Melvyn I.
• Application Number:
  US06/238,522
• Time in Patent Office: 425 Days
• Field of Search: 526/279, 528/32, 528/26, 351/160 R, 351/160 H
• US Class Current: 526/279
• CPC Class Codes: C08F 283/124 on to polysiloxanes having carbon-to-carbon double bonds
• CPC Class Codes: C08F 30/08 containing silicon
• 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: 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 endcapped with activated unsaturated groups are copolymerized with cycloalkyl modulus modifiers and tear film stabilizers to form hard, gas permeable, polysiloxane contact lenses and other biomedical devices.

Claims

1. A shaped article suitable for use in biomedical applications being a polymer formed by polymerizing (a) one or more polysiloxane monomers α

,ω

terminally bonded through divalent hydrocarbon groups to an activated unsaturated group with (b) a cycloalkyl modulus modifier and (c) a tear film stabilizer to form a crosslinked three-dimensional polymeric network.

2. The article of claim 1 wherein the modulus modifier is present in an amount from 90 to 30 parts per 10 to 70 parts of polysiloxane monomers and the sum of parts equals 100.

3. The article according to claim 2 wherein from 70 to 40 parts of modulus modifier are present.

4. The article according to claim 3 wherein 55 parts of modulus modifier are present.

5. The article according to claim 1 wherein the cycloalkyl modifier is of the formula ##STR5## wherein:

D is branched or normal alkyl of 3 to 6 carbon atoms

E is H or CH₃

Z is H or CH₃

n is an integer from 3 to 8.

6. The article according to claim 5 wherein D is a branched alkyl of 3 or 4 carbon atoms and n is an integer from 4 to 6.

7. The article according to claim 6 wherein the modifier is tertiarybutylcyclohexyl methacrylate.

8. The article according to claim 2 wherein 2 to 20 parts of tear film stabilizer are present per 100 parts of modulus modifier and polysiloxane monomer.

9. The article according to claim 8 wherein 3 to 12 parts of tear film stabilizer are employed.

10. The article according to claim 9 wherein from 5 to 9 parts of tear film stabilizer are present.

11. The article according to claim 1 wherein the tear film stabilizer is selected from the group consisting of hydroxyethylmethacrylate, hydroxyethylacrylate, hydroxypropylmethacrylate, hydropropylacrylate and mixtures thereof.

12. The article according to claim 11 wherein the tear film stabilizer is hydroxyethylmethacrylate.

13. The article according to claim 1 wherein an auxiliary modifier selected from the group consisting of tertiary-butyl acrylate, polyethylene glycol methacrylate, polyethylene glycol dimethacrylate, 1,3-bis(4-methacryloxybutyl) tetramethyl disiloxane, polyethylene glycol acrylate, polyethylene glycol diacrylate, divinyl benzene, divinyl alkyl benzene mixtures thereof is present in an amount of up to 20 parts by weight per 100 parts of tertiary-butyl styrene and polysiloxane.

14. The article according to claim 13 wherein from zero to 10 parts auxiliary modifier are present.

15. The article according to claim 1 wherein the polysiloxane is a poly(organosiloxane) of the formula ##STR6## 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 each is a monovalent hydrocarbon radical each having from 1 to about 12 carbon atoms and m is an integer from 0 to 100.

16. The article according to claim 15 wherein A is methacryloxy, 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 are selected from the group consisting of monovalent hydrocarbon radical or a halogen substituted monovalent hydrocarbon radical each having from 1 to 12 carbon atoms and m is an integer from 0 to 50.

17. The article according to claim 16 wherein R is an alkylene radical and R¹, R², R³ and R⁴ are each analkyl radical having from 1 to 10 carbon atoms.

18. The article according to claim 17 wherein m is a number from 0 to about 25.

19. The article according to claim 1 wherein the polysiloxane is a polyparaffinsiloxane of the formula ##STR7## where 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 are ach independently 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 and a halogen substituted monovalent hydrocarbon radical having from 1 to about 12 carbon atoms;

R⁵ and R⁶ 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 --C(O)OR⁷ wherein R⁷ is selected from the group consisting of a hydrocarbon group containing from 1 to 12 carbon atoms and a carboxylic acid amide represented by the formula --C(O)NR⁸ R⁹ wherein R⁸ and R⁹ 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 n is an integer of 1 to about 100.

20. The article according to claim 19 wherein R is an alkylene radical, R¹, R², R³ and R⁴ are each an alkyl radical having from 1 to 10 carbon atoms and R⁵ and R⁶ are each hydrogen or methyl and n is an integer from 1 to 50.

21. The article according to claim 20 wherein n is a number from 1 to about 25 and x is an integer from 2 to 10.

22. The article according to claim 21 wherein x is 2 or 3.

23. The article according to claim 1 has a flexural modulus of at least 1,000 Kg/cm².

24. Wherein the article according to claim 1 is a gas permeable hard contact lens.