US4743667A
Expired / Lapsed
US
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Contact lens material
Assignee: Menicon Co Ltd
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Filing: 1986-07-22
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Granted: 1988-05-10
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Expires: 2006-07-22
Abstract
Abstract The invention relates to novel multifunctional organosiloxane monomers which can be represented by the general formulas: ##STR1## wherein, at least one of "X 1 "-"X 7 " is a group of the following structure: ##STR2## and its copolymerization with monofunctional organosiloxane monomers which can be represented by the general formulas: ##STR3## and alkyl and/or cyclic alkyl esters of acrylic, methacrylic acids and/or itaconate esters, and in some cases fluoroalkyl esters of acrylic, methacrylic acids and/or fluoroalkyl itaconate esters to produce excellent oxygen permeable hard contact lens material. Preferably, the copolymer includes cross-linking agents and wetting agents. Contact lenses manufactured from the materials can be easily machined and polished into hard contact lenses having solvent-resistance and sufficient permeabilities.
Inventors
- 👤 Yutaka Mizutani
- 👤 Tatsuo Harata
- 👤 Naokatsu Tanahashi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 07:10
CPC Classifications
C; C08; C08F; C08F230/00; C08F230/04; C08F230/08; G; G02; G02B; G02B1/00; G02B1/04; G02B1/041; G02B1/043
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
311 words
An oxygen-permeable, solvent-resistant, dimensionally stable, hard contact lens material consisting essentially of a copolymer formed by free radical polymerization of (a) at least one multifunctional organosiloxane monomer represented by the formulas: ##STR34## wherein "X 1 "-"X 7 " are selected from the class consisting of C 1 -C 6 alkyl groups, cyclic alkyl groups, phenyl groups and "Y" groups, at least one of "X 1 "-"X 7 " being "Y" group; "Y" is a group of the following structure: ##STR35## "R 1 " is hydrogen or methyl radical; "A 1 "-"A 12 " are selected from the class consisting of C 1 -C 6 alkyl groups, cyclic alkyl groups, phenyl groups and "Z" groups; "Z" is a group of the following structure: ##STR36## "R 2 ", "R 2' " and "R 3 " are selected from the class consisting of C 1 -C 6 alkyl groups, cyclic alkyl groups and phenyl groups; "k", "k'", "l", "l'", "m", "m'" and n are integers from 0 to 10; and mixture thereof, (b) at least one monofunctional organosiloxane monomer represented by the formulas: ##STR37## wherein "R 1 " is hydrogen or methyl radical; "A 1 ", "A 2 ", "A 2' " and "A 3 " are selected from the class consisting of C 1 -C 6 alkyl groups and phenyl groups; "D" and "E" are selected from the class consisting of C 1 -C 6 alkyl groups, phenyl groups and the following groups: ##STR38## "R 2 ", "R 2' " and "R 3 " are selected from the class consisting of C 1 -C 6 alkyl groups and phenyl groups; "q" is an integer from 1 to 3; and mixture thereof, (c) at least one comonomer selected from the class consisting of C 1 -C 10 alkyl, cyclic alkyl or substituted phenyl esters of acrylic, methacrylic acids and itaconate esters and cross-linking agents.
Claim 2
Dependent Claim
311 words
An oxygen-permeable, solvent-resistant, dimensionally stable, hard contact lens material consisting essentially of a copolymer formed by free radical polymerization of (a) at least one multifunctional organosiloxane monomer represented by the formulas: ##STR34## wherein "X 1 "-"X 7 " are selected from the class consisting of C 1 -C 6 alkyl groups, cyclic alkyl groups, phenyl groups and "Y" groups, at least one of "X 1 "-"X 7 " being "Y" group; "Y" is a group of the following structure: ##STR35## "R 1 " is hydrogen or methyl radical; "A 1 "-"A 12 " are selected from the class consisting of C 1 -C 6 alkyl groups, cyclic alkyl groups, phenyl groups and "Z" groups; "Z" is a group of the following structure: ##STR36## "R 2 ", "R 2' " and "R 3 " are selected from the class consisting of C 1 -C 6 alkyl groups, cyclic alkyl groups and phenyl groups; "k", "k'", "l", "l'", "m", "m'" and n are integers from 0 to 10; and mixture thereof, (b) at least one monofunctional organosiloxane monomer represented by the formulas: ##STR37## wherein "R 1 " is hydrogen or methyl radical; "A 1 ", "A 2 ", "A 2' " and "A 3 " are selected from the class consisting of C 1 -C 6 alkyl groups and phenyl groups; "D" and "E" are selected from the class consisting of C 1 -C 6 alkyl groups, phenyl groups and the following groups: ##STR38## "R 2 ", "R 2' " and "R 3 " are selected from the class consisting of C 1 -C 6 alkyl groups and phenyl groups; "q" is an integer from 1 to 3; and mixture thereof, (c) at least one comonomer selected from the class consisting of C 1 -C 10 alkyl, cyclic alkyl or substituted phenyl esters of acrylic, methacrylic acids and itaconate esters and cross-linking agents.
Claim 3
Dependent Claim
39 words
The oxygen-permeable hard contact lens material according to claim 1, wherein said cross-linking agents include multifunctional compounds such as: ethylene glycol diacrylate and dimethacrylate, diethylene glycol diacrylate and dimethacrylate, triethylene glycol diacrylate and dimethacrylate, tetraethylene glycol diacrylate and dimethacrylate,
Claim 4
Dependent Claim
36 words
3-butanediol diacrylate and dimethacrylate, 1,4-butanediol diacrylate and dimethacrylate, 1,6-hexanediol diacrylate and dimethacrylate, neopentyl glycol diacrylate and dimethacrylate, trimethylol propane triacrylate and trimethacrylate, pentaerythrytol tetraacrylate and tetramethacrylate, diacryloxybenzophenone and dimethacryloxybenzophenone, diacryloxy dimethoxy benzophenone and dimethacryloxy dimethoxy benzophenone.
Claim 5
Dependent Claim
36 words
3-butanediol diacrylate and dimethacrylate, 1,4-butanediol diacrylate and dimethacrylate, 1,6-hexanediol diacrylate and dimethacrylate, neopentyl glycol diacrylate and dimethacrylate, trimethylol propane triacrylate and trimethacrylate, pentaerythrytol tetraacrylate and tetramethacrylate, diacryloxybenzophenone and dimethacryloxybenzophenone, diacryloxy dimethoxy benzophenone and dimethacryloxy dimethoxy benzophenone.
Claim 6
Dependent Claim
64 words
The oxygen-permeable hard contact lens material according to claim 1, wherein said copolymer is formed by free radical polymerization of 2 to 80 parts by weight of said multifunctional organosiloxane monomer 5 to 60 parts by weight of said monofunctional organosiloxane monomer and 0.5 to 95 parts by weight of said C 1 -C 10 alkyl, cyclic alkyl, substituted phenyl esters and/or cross-linking agents.
Claim 7
Dependent Claim
60 words
The oxygen-permeable hard contact lens material according to claim 3, wherein said copolymer further includes at least one wetting agent selected from the class consisting of 2-hydroxy ethyl acrylate and methacrylate, 2-hydroxy propyl acrylate and methacrylate, 2-hydroxy butyl acrylate and methacrylate, diethylene glycol monoacrylate and monomethacrylate, triethylene glycol monoacrylate and monomethacrylate, acrylic acid, methacrylic acid, acrylamide, methacrylamide, N-methylol methacrylamide, N-vinyl-2-pyrrolidone.
Claim 8
Dependent Claim
26 words
The oxygen-permeable hard contact lens material according to claim 4, wherein said copolymer includes 1 to 20% by weight of entire mixture of said wetting agents.
Claim 9
Dependent Claim
65 words
The oxygen-permeable hard contact lens material according to claim 5, wherein said copolymer further includes at least one fluoroalkyl ester monomer represented by the formulas: ##STR39## wherein "U" and "V" are selected from the class consisting of hydrogen and trifluoromethyl radical; "R" is hydrogen or methyl radical; "h" is 1 or 2; "i" is an integer from 1 to 10; "j" is 0 or 1.
Claim 10
Dependent Claim
24 words
The oxygen-permeable hard contact lens material according to claim 6, wherein said copolymer include 5 to 50% by weight of said fluoroalkyl ester monomer.
Claim 11
Dependent Claim
55 words
The oxygen-permeable hard contact lens material according to claim 5, wherein said copolymer further includes at least one fluoro monomer having phenyl group from the class consisting of o-trifluoromethyl benzyl acrylate and methacrylate, bis(o-trifluoromethyl benzyl)itaconate, p-trifluoromethyl benzyl acrylate and methacrylate, bis(p-trifluoromethyl benzyl)itaconate, 2,2,2,2',2',2'-hexafluoro cumyl acrylate and methacrylate, bis(2,2,2,2',2',2'-hexafluoro cumyl)itaconate, 1,3-bis(2-acryloxy hexafluoro isopropyl)benzene, 1,3-bis(2-methacryloxy hexafluoro isopropyl)benzene.
Claim 12
Dependent Claim
25 words
The oxygen-permeable hard contact lens material according to claim 8, wherein said copolymer include 2-50% by weight of entire mixture of said oxygen-permeable rigid modifier.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-05-10 | 1991-11-09 | 1992-05-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-05-10 | 1995-11-09 | 1996-05-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-05-10 | 1999-11-09 | 2000-05-10 | $7700.00 | Window Closed / Lapsed |