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US4355147A Expired / Lapsed US ⏱️ 0.0 years remaining

Polysiloxane with polycyclic modifier composition and biomedical devices

Assignee: Bausch and Lomb Inc
•
Filing: 1981-02-26
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Granted: 1982-10-19
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Expires: 2001-02-26
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Abstract

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.

Inventors

  • 👤 William G. Deichert
  • 👤 Gary D. Friends
  • 👤 John B. Melpolder
  • 👤 Joon S. Park

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-25 04:15
CPC Classifications
C; C08; C08F; C08F283/00; C08F283/12; C08F283/124; Y; Y10; Y10S; Y10S128/00; Y10S128/21

Claims Analysis

Total Claims: 18
Claim 1
Independent Claim 154 words
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/cm 2 .
Claim 2
Dependent Claim 154 words
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/cm 2 .
Claim 3
Dependent Claim 16 words
The article according to claim 1 wherein from 90 to 40 parts of modifier are present.
Claim 4
Dependent Claim 12 words
The article according to claim 2 wherein the modifier is isobornyl methacrylate.
Claim 5
Dependent Claim 17 words
The article according to claim 1 wherein 3 to 12 parts of tear film stabilizer are employed.
Claim 6
Dependent Claim 18 words
The article according to claim 1 wherein from 5 to 9 parts of tear film stabilizer are present.
Claim 7
Dependent Claim 13 words
The article according to claim 1 wherein the tear film stabilizer is hydroxyethylmethacrylate.
Claim 8
Dependent Claim 60 words
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.
Claim 9
Dependent Claim 24 words
The article according to claim 7 wherein from zero to 10 parts of auxiliary modifier are present per 100 parts of modifier and polysiloxane.
Claim 10
Dependent Claim 86 words
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, R 1 , R 2 , R 3 and R 4 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.
Claim 11
Dependent Claim 77 words
The article according to claim 9 wherein A is methacryloxy, 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 or a halogen substituted monovalent hydrocarbon radical each having from 1 to 12 carbon atoms and m is an integer from 0 to 50.
Claim 12
Dependent Claim 36 words
The article according to claim 10 wherein R is an alkylene radical and R 1 , R 2 , R 3 and R 4 are each an alkyl radical having from 1 to 10 carbon atoms.
Claim 13
Dependent Claim 16 words
The article according to claim 11 wherein m is a number from 0 to about 25.
Claim 14
Dependent Claim 212 words
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; R 1 , R 2 , R 3 and R 4 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; 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, carboxylic acid ester group represented by the formula --C(O)OR 7 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 --C(O)NR 8 R 9 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 n is an integer of 1 to about 100.
Claim 15
Dependent Claim 55 words
The article according to claim 4 wherein R is an alkylene radical, R 1 , R 2 , R 3 and R 4 are each an alkyl radical having from 1 to 10 carbon atoms and R 5 and R 6 are each hydrogen or methyl and n is an integer from 1 to 50.
Claim 16
Dependent Claim 25 words
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.
Claim 17
Dependent Claim 12 words
The article according to claim 15 wherein x is 2 or 3.
Claim 18
Dependent Claim 14 words
Wherein the article according to claim 1 is a gas permeable hard contact lens.

References Cited (Backward Citations)

US3639362A Cited
US3808178A Cited
US4153641A Cited
US4208506A Cited
US4152508A Cited
US4228269A Cited
GB2036765A Cited
US4276402A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1985-10-18 1986-04-19 1986-10-19 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-10-18 1990-04-19 1990-10-19 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-10-18 1994-04-19 1994-10-19 $7700.00 Window Closed / Lapsed

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