Polysiloxane with polycyclic modifier composition and biomedical devices

• US 4,355,147 A
• Filed: 02/26/1981
• Issued: 10/19/1982
• Est. Priority Date: 02/26/1981
• Status: Expired due to Fees

• Current Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Original Assignee: Bausch & Lomb Incorporated (Bausch Health Cos., Inc.)
• Inventors: Park, Joon S., Friends, Gary D., Melpolder, John B., Deichert, William G.
• Primary Examiner(s): BRIGGS SR, WILBERT
• Application Number:
  US06/238,524
• Time in Patent Office: 600 Days
• Field of Search: 528/26, 528/29, 528/24, 526/264, 526/263, 526/279, 204/159.13
• US Class Current: 526/264
• CPC Class Codes: C08F 283/124 on to polysiloxanes having carbon-to-carbon double bonds
• CPC Class Codes: Y10S 128/21 Silicone

Abstract

Monomeric polysiloxanes endcapped with activated unsaturated groups are copolymerized with polycyclic 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 polycyclic modulus modifier and (c) a tear film stabilizer to form a crosslinked three-dimensional polymeric network,

said modulus modifier being selected from the group consisting of isobornyl acrylate, isobornyl methacrylate, dicyclopentandienyl acrylate, dicyclopentadienyl methacrylate, adamantanyl acrylate, adamantanyl methacrylate, isopinocamphyl acrylate and isopinocamphyl methacrylate and 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,

said stabilizer being selected from the group consisting of hydroxyethylmethacrylate, hydroxyethylacrylate, hydroxypropylmethacrylate, hydroxypropylacrylate and mixtures thereof and is present in an amount from 2 to 20 parts per 100 parts of modulus modifier and polysiloxane monomers,

said polymer having a flexural modulus of at least 1,500 Kg/cm².

2. The article according to claim 1 wherein from 90 to 40 parts of modifier are present.

3. The article according to claim 2 wherein the modifier is isobornyl methacrylate.

4. The article according to claim 1 wherein 3 to 12 parts of tear film stabilizer are employed.

5. The article according to claim 1 wherein from 5 to 9 parts of tear film stabilizer are present.

6. The article according to claim 1 wherein the tear film stabilizer is hydroxyethylmethacrylate.

7. 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 modifier and polysiloxane.

8. The article according to claim 7 wherein from zero to 10 parts of auxiliary modifier are present per 100 parts of modifier and polysiloxane.

9. The article according to claim 1 wherein the polysiloxane is a poly(organosiloxane) of the formula ##STR4## 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 or a halogen substituted monovalent hydrocarbon radical each having from 1 to about 12 carbon atoms and m is an integer from 0 to 100.

10. The article according to claim 9 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 a 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.

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

12. The article according to claim 11 wherein m is a number from 0 to about 25.

13. The article according to claim 1 wherein the polysiloxane is a polyparaffinsiloxane of the formula ##STR5## 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 are each 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;

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, 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 about 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.

14. The article according to claim 4 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.

15. The article according to claim 14 wherein n is a number from 1 to about 25 and x is an integer from 2 to 10.

16. The article according to claim 15 wherein x is 2 or 3.

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