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US4276402A Expired / Lapsed US ⏱️ 0.0 years remaining

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

Assignee: Bausch and Lomb Inc
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Filing: 1979-09-13
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Granted: 1981-06-30
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Expires: 1999-09-13
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Abstract

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.

Inventors

  • 👤 Richard C. Chromecek
  • 👤 William G. Deichert
  • 👤 Joseph J. Falcetta
  • 👤 Martin F. vanBuren

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-26 12:28
CPC Classifications
C; C08; C08L; C08L43/00; C08L43/04; C08F; C08F283/00; C08F283/12; C08F283/124; C08G; C08G77/00; C08G77/48; C08G77/50

Claims Analysis

Total Claims: 32
Claim 1
Independent Claim 150 words
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.
Claim 2
Dependent Claim 150 words
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.
Claim 3
Dependent Claim 30 words
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.
Claim 4
Dependent Claim 17 words
The contact lens according to claim 2 wherein the polycyclic ester of acrylic acid is isobornyl acrylate.
Claim 5
Dependent Claim 24 words
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.
Claim 6
Dependent Claim 31 words
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.
Claim 7
Dependent Claim 25 words
The contact lens according to claim 1 wherein the tensile modulus of elasticity is from about 50 g/mm 2 to about 8000 g/mm 2 .
Claim 8
Dependent Claim 13 words
The contact lens according to claim 1 wherein the lens is substantially transparent.
Claim 9
Dependent Claim 295 words
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, R 1 , R 2 , R 3 and R 4 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 A 1 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.
Claim 10
Dependent Claim 17 words
The contact lens according to claim 8 wherein m is a number from 50 to about 800.
Claim 11
Dependent Claim 19 words
The contact lens according to claim 9 wherein m is a number of from about 50 to about 200.
Claim 12
Dependent Claim 22 words
The contact lens according to claim 10 which has a Shore hardness of 80 or below on the Shore hardness scale A.
Claim 13
Dependent Claim 22 words
The contact lens according to claim 11 which has a Shore hardness of 45 to 55 on the Shore hardness scale A.
Claim 14
Dependent Claim 22 words
The contact lens according to claim 8 which has an oxygen transportability of at least 2×10 -6 cm 3 /(sec.cm 2 atm.).
Claim 15
Dependent Claim 54 words
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 R 1 , R 2 , R 3 and R 4 are alkyl radicals having from 1 to 10 carbon atoms.
Claim 16
Dependent Claim 20 words
The contact lens according to claim 14 wherein the alkylene radical has from about 1 to about 4 carbon atoms.
Claim 17
Dependent Claim 20 words
The contact lens according to claim 16 wherein the alkylene radical has from about 3 to about 4 carbon atoms.
Claim 18
Dependent Claim 33 words
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.
Claim 19
Dependent Claim 22 words
The contact lens according to claim 17 wherein R 1 , R 2 , R 3 and R 4 are methyl radicals.
Claim 20
Dependent Claim 18 words
The contact lens according to claim 8 wherein m' is a number of from 1 to about 800.
Claim 21
Dependent Claim 17 words
The contact lens according to claim 19 wherein m' is a number from about 20 to 500.
Claim 22
Dependent Claim 19 words
The contact lens according to claim 20 wherein m' is a number of from about 20 to about 200.
Claim 23
Dependent Claim 21 words
The contact lens according to claim 8 wherein the oxygen transportability is at least 2×10 -6 cm 3 /(sec.cm 2 atm.).
Claim 24
Dependent Claim 22 words
The contact lens according to claim 22 which has a Shore hardness of 80 or below on the Shore hardness scale A.
Claim 25
Dependent Claim 16 words
The contact lens according to claim 8 wherein x is a number from 2 to 3.
Claim 26
Dependent Claim 52 words
The contact lens according to claim 8 wherein A 1 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.
Claim 27
Dependent Claim 20 words
The contact lens according to claim 25 wherein the alkylene radical has from about 1 to about 4 carbon atoms.
Claim 28
Dependent Claim 20 words
The contact lens according to claim 26 wherein the alkylene radical has from about 3 to about 4 carbon atoms.
Claim 29
Dependent Claim 33 words
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.
Claim 30
Dependent Claim 22 words
The contact lens according to claim 28 wherein R' 1 , R' 2 , R' 3 and R' 4 are methyl radicals.
Claim 31
Dependent Claim 23 words
The contact lens according to claim 29 wherein R' 5 and R' 6 are selected from the group consisting of hydrogen and methyl.
Claim 32
Dependent Claim 16 words
The contact lens according to claim 30 wherein x is a number from 2 to 3.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-06-29 1984-12-29 1985-06-30 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-06-29 1988-12-29 1989-06-30 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-06-29 1992-12-29 1993-06-30 $7700.00 Window Closed / Lapsed

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