US4208506A
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Polyparaffinsiloxane shaped article for use in biomedical applications
Assignee: Bausch and Lomb Inc
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Filing: 1979-02-22
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Granted: 1980-06-17
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Expires: 1999-02-22
Abstract
Abstract Monomeric polyparaffinsiloxanes end-capped with activated unsaturated groups and polymers and copolymers thereof are disclosed herein for use as contact lenses and biomedical devices with improved properties, such as, oxygen transportability, hydrolytic stability, biological inertness, transparency and improved strength without the use of fillers. The polymer composition comprises a poly(organoparaffinsiloxane) monomer α,ω terminally bonded through divalent hydrocarbon groups to polymerized free radical polymerizably activated unsaturated groups.
Inventors
- 👤 William G. Deichert
- 👤 Kai C. Su
- 👤 Martin F. vanBuren
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 04:33
CPC Classifications
G; G02; G02B; G02B1/00; G02B1/04; G02B1/041; G02B1/043; C; C08; C08G; C08G77/00; C08G77/04; C08G77/20; C08L; C08L83/00; C08L83/14; Y; Y10; Y10S; Y10S128/00; Y10S128/21
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
229 words
A fillerless, hydrolytically stable, biologically inert, transparent, oxygen transporting, polymeric, shaped article for use in biomedical applications comprising polymerizing a poly(organoparaffinsiloxane) monomer represented by the following formula: ##STR28## 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 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 ##STR29## 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 ##STR30## 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, forming a polymer in a crosslinked network.
Claim 2
Dependent Claim
229 words
A fillerless, hydrolytically stable, biologically inert, transparent, oxygen transporting, polymeric, shaped article for use in biomedical applications comprising polymerizing a poly(organoparaffinsiloxane) monomer represented by the following formula: ##STR28## 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 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 ##STR29## 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 ##STR30## 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, forming a polymer in a crosslinked network.
Claim 3
Dependent Claim
59 words
The shaped article for use in biomedical applications according to claim 1 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 R 1 , R 2 , R 3 and R 4 are alkyl radicals having from 1 to 10 carbon atoms.
Claim 4
Dependent Claim
23 words
The shaped article for use in biomedical applications according to claim 2 wherein m is a number of from 1 to about 200.
Claim 5
Dependent Claim
22 words
The shaped article for use in biomedical applications according to claim 3 wherein m is a number from 1 to about 50.
Claim 6
Dependent Claim
22 words
The shaped article for use in biomedical applications according to claim 4 wherein m is a number from 1 to about 25.
Claim 7
Dependent Claim
21 words
The shaped article for use in biomedical applications according to claim 1 wherein x is a number from 2 to 3.
Claim 8
Dependent Claim
16 words
The shaped article for use in biomedical applications according to claim 1 is a contact lens.
Claim 9
Dependent Claim
253 words
A fillerless, hydrolytically stable, biologically inert, transparent, oxygen transporting, polymeric shaped article for use in biomedical applications comprising a poly (organoparaffinsiloxane) monomer represented by the following formula: ##STR31## 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 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 ##STR32## 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 ##STR33## 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, copolymerized with one or more monomers selected from the group consisting of a lower ester of acrylic and methacrylic acid, styryls, and N-vinyl pyrrolidinone forming a copolymer in a crosslinked network.
Claim 10
Dependent Claim
253 words
A fillerless, hydrolytically stable, biologically inert, transparent, oxygen transporting, polymeric shaped article for use in biomedical applications comprising a poly (organoparaffinsiloxane) monomer represented by the following formula: ##STR31## 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 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 ##STR32## 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 ##STR33## 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, copolymerized with one or more monomers selected from the group consisting of a lower ester of acrylic and methacrylic acid, styryls, and N-vinyl pyrrolidinone forming a copolymer in a crosslinked network.
Claim 11
Dependent Claim
31 words
The shaped article for use in biomedical applications according to claim 8 wherein the monomers are selected from the group consisting of tertiary butyl styrene, propyl styrene, styrene and N-vinyl pyrrolidone.
Claim 12
Dependent Claim
48 words
The shaped article for use in biomedical applications according to claim 8 wherein the monomer is selected from the group consisting of allyl methacrylate, butoxyethylmethacrylate, cyclohexyl methacrylate, ethyl methacrylate, methylmethacrylate, ethyl hexyl acrylate, n-butyl acrylate, butyl acrylate, N-vinyl pyrrolidinone, isobornyl acrylate, menthyl acrylate, adamantanyl acrylate and isopinocamphyl acrylate.
Claim 13
Dependent Claim
21 words
The shaped article for use in biomedical applications according to claim 8 wherein x is a number from 2 to 3.
Claim 14
Dependent Claim
16 words
The shaped article for use in biomedical applications according to claim 8 is a contact lens.
Claim 15
Dependent Claim
232 words
A fillerless, flexible, hydrolytically stable, biologically inert, transparent, resilient, soft, oxygen transporting, polymeric, shaped article for use in biomedical applications comprising polymerizing a poly(organosiloxane) monomer represented by the following formula: ##STR34## 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 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 ##STR35## 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 ##STR36## 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 forming a polymer in a crosslinked network.
Claim 16
Dependent Claim
232 words
A fillerless, flexible, hydrolytically stable, biologically inert, transparent, resilient, soft, oxygen transporting, polymeric, shaped article for use in biomedical applications comprising polymerizing a poly(organosiloxane) monomer represented by the following formula: ##STR34## 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 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 ##STR35## 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 ##STR36## 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 forming a polymer in a crosslinked network.
Claim 17
Dependent Claim
24 words
The shaped article for use in biomedical applications according to claim 13 wherein m is a number of from about 50 to about 800.
Claim 18
Dependent Claim
60 words
The shaped article for use in biomedical applications according to claim 14 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 R 1 , R 2 , R 3 and R 4 is an alkyl radical having from 1 to 10 carbon atoms.
Claim 19
Dependent Claim
25 words
The shaped article for use in biomedical applications according to claim 15 wherein the alkylene radical has from about 1 to about 4 carbon atoms.
Claim 20
Dependent Claim
25 words
The shaped article for use in biomedical applications according to claim 16 wherein the alkylene radical has from about 3 to about 4 carbon atoms.
Claim 21
Dependent Claim
38 words
The shaped article for use in biomedical applications according to claim 17 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 22
Dependent Claim
28 words
The shaped article for use in biomedical applications according to claim 18 wherein R 1 , R 2 , R 3 , and R 4 are methyl radicals.
Claim 23
Dependent Claim
23 words
The contact lens according to claim 19 wherein R 5 and R 6 are selected from the group consisting of hydrogen and methyl.
Claim 24
Dependent Claim
21 words
The shaped article for use in biomedical applications according to claim 13 wherein x is a number from 2 to 3.
Claim 25
Dependent Claim
16 words
The shaped article for use in biomedical applications according to claim 13 is a contact lens.
Claim 26
Dependent Claim
255 words
A fillerless, flexible, hydrolytically stable, biologically inert, transparent, resilient, soft, oxygen transporting, polymeric, shaped article for use in biomedical applications comprising a poly(organosiloxane) monomer represented by the following formula: ##STR37## 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 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 ##STR38## 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 ##STR39## 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 copolymerized with one or more monomers selected from the group consisting of a lower ester of acrylic and methacrylic acid, styryls, and N-vinyl pyrrolidone forming a polymer in a crosslinked network.
Claim 27
Dependent Claim
255 words
A fillerless, flexible, hydrolytically stable, biologically inert, transparent, resilient, soft, oxygen transporting, polymeric, shaped article for use in biomedical applications comprising a poly(organosiloxane) monomer represented by the following formula: ##STR37## 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 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 ##STR38## 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 ##STR39## 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 copolymerized with one or more monomers selected from the group consisting of a lower ester of acrylic and methacrylic acid, styryls, and N-vinyl pyrrolidone forming a polymer in a crosslinked network.
Claim 28
Dependent Claim
31 words
The shaped article for use in biomedical applications according to claim 23 wherein the monomers are selected from the group consisting of tertiary butyl styrene, propyl styrene, styrene and N-vinyl pyrrolidone.
Claim 29
Dependent Claim
44 words
The shaped article for use in biomedical applications according to claim 23 wherein the monomer is selected from the group consisting of allyl methacrylate, butoxyethylmethacrylate, ethyl hexyl acrylate, n-butyl acrylate, butyl acrylate and N-vinyl pyrrolidone, isobornyl acrylate, menthyl acrylate, adamantanyl acrylate and isopinocamphyl acrylate.
Claim 30
Dependent Claim
21 words
The shaped article for use in biomedical applications according to claim 25 wherein x is a number from 2 to 3.
Claim 31
Dependent Claim
16 words
The shaped article for use in biomedical applications according to claim 26 is a contact lens.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-06-17 | 1983-12-17 | 1984-06-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-06-17 | 1987-12-17 | 1988-06-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-06-17 | 1991-12-17 | 1992-06-17 | $7700.00 | Window Closed / Lapsed |