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US3856758A
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Polymers of cyano-substituted norbornene derivatives and method for preparing the same
Assignee: Resonac Holdings Corp
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Filing: 1973-03-27
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Granted: 1974-12-24
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Expires: 1993-03-27
Abstract
Abstract WHERE: W, X, Y and Z radicals selected from the group consisting of hydrogen, nitrile group, substituents including nitrile group, alkyl radical having 1 to 20 carbon carbon atoms, alkenyl radical having 1 to 20 carbon atoms, aryl radical having 6 to 20 carbon atoms and aralkyl radical having 7 to 20 carbon atoms; and at least one of said W, X, Y and Z is the racidical selected from the group consisting of nitrile group and substituents including nitrile group. Polymers prepared with a reduced viscosity of 0.1 to 20 by ringopening polymerization of cyano-substituted norbornene derivatives, whose chemical structure may be expressed by the following general formula:
Inventors
- 👤 T Ueshima
- 👤 S Kobayashi
- 👤 M Matsuoka
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 14:23
CPC Classifications
C; C08; C08G; C08G61/00; C08G61/02; C08G61/04; C08G61/06; C08G61/08
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
23 words
POLYMERS PREPARED WITH A REDUCED VISCOSITY OF 0.1 TO 20 BY RING-OPENING POLYMERIZATION OF CYANO-SUBSTITUTED NORBORNENE DERIVATIVES EXPRESSED BY THE FOLLOWING GENERAL FORMULA
Claim 2
Dependent Claim
23 words
POLYMERS PREPARED WITH A REDUCED VISCOSITY OF 0.1 TO 20 BY RING-OPENING POLYMERIZATION OF CYANO-SUBSTITUTED NORBORNENE DERIVATIVES EXPRESSED BY THE FOLLOWING GENERAL FORMULA
Claim 3
Dependent Claim
33 words
Polymers according to claim 1 wherein the substituents containing nitrile group are selected from the group consisting of the cyanomethyl radical, cyanoethyl radical, cyanopropyl radical, cyano-n-butyl radical, cyano-isobutyl radical and omega -cyano-n-heptyl radical.
Claim 4
Dependent Claim
70 words
Polymers according to claim 1 wherein the cyano-substituted norbornene derivatives are selected from the group consisting of 5-cyano bicyclo (2, 2, 1)-heptene-2, 5-cyano-5-methyl bicyclo (2, 2, 1)-heptene-2, 5-cyano-5-n-octyl bicyclo (2, 2, 1)-heptene-2, 5,5-dicyano bicyclo (2, 2, 1)-heptene-2, 5,6-dicyano bicyclo (2, 2, 1)-heptene-2, 5-cyano -6-phenyl bicyclo (2, 2, 1- omega -heptene-2, and a mixture of 5- -cyano-n-heptyl, 6-n-2-octenyl bicyclo (2, 2, 1)-heptene-2 and 5- omega -cyano-2-decenyl, 6-n-pentyl bicyclo (2, 2, 1)-heptene-2.
Claim 5
Independent Claim
15 words
A method for manufacturing the polymers of cyano-substituted norbornene derivatives expressed by the general formula
Claim 6
Independent Claim
15 words
A method for manufacturing the polymers of cyano-substituted norbornene derivatives expressed by the general formula
Claim 7
Dependent Claim
52 words
A method according to claim 4 wherein the ring-opening polymerization is effected in the presence of a catalytic system prepared by adding to the catalytic system of claim 4 at least one compound selected from the group consisting of water, peroxides, epoxides, organic halides, acetal compounds, orthocarboxylic acid esters and alcoholic compounds.
Claim 8
Dependent Claim
20 words
A method according to claim 4 wherein the ring-opening polymerization is carried out in the presence of an organic solvent.
Claim 9
Dependent Claim
19 words
A method according to claim 5 wherein the ring-opening polymerization is conducted in the presence of an organic solvent.
Claim 10
Dependent Claim
93 words
A method according to claim 4 wherein the organic aluminium compounds are selected from the group consisting of compounds represented by the general formulas AlR3, AlRnX3 n and a mixture of compounds represented by said general formula AlR3 and water (in which the mol ratio of H2O to AlR3 has a value of <1.5) where R is a radical selected from the group consisting of the alkyl radical and aryl radical, X is a radical selected from the group consisting of halogens, hydrogen and alkoxy radical, and n is 1, 1.5 and 2.
Claim 11
Dependent Claim
93 words
A method according to claim 5 wherein the organic aluminium compounds are selected from the group consisting of compounds represented by the general formulas AlR3, AlRnX3 n and a mixture of compounds represented by said general formula AlR3 and water (in which the mol ratio of H2O to AlR3 has a value of <1.5) where R is a radical selected from the group consisting of the alkyl radical and aryl radical, X is a radical selected from the group consisting of halogens, hydrogen and alkoxy radical, and n is 1, 1.5 and 2.
Claim 12
Dependent Claim
40 words
A method according to claim 8 wherein compounds expressed by the general formula AlR3 are selected from the group consisting of trimethyl aluminium, triethyl aluminium, tri-n-propyl aluminium, tri-isopropyl aluminium, tri-isobutyl aluminium, trihexyl aluminium, trioctyl aluminium, tribenzyl aluminium, and triphenyl aluminium.
Claim 13
Dependent Claim
40 words
A method according to claim 9 wherein compounds expressed by the general formula AlR3 are selected from the group consisting of trimethyl aluminium, triethyl aluminium, tri-n-propyl aluminium, tri-isopropyl aluminium, tri-isobutyl aluminium, trihexyl aluminium, trioctyl aluminium, tribenzyl aluminium, and triphenyl aluminium.
Claim 14
Dependent Claim
102 words
A method according to claim 8 wherein the compounds expressed by the general formula AlRnX3 n are selected from the group consisting of diethyl aluminium monochloride, di-n-propyl aluminium monochloride, diisobutyl aluminium monochloride, di-n-butyl aluminium monochloride, diethyl aluminium monobromide, diethyl aluminium monoiodide, diethyl aluminium monohydride, di-n-propyl aluminium monohydride, diisobutyl aluminium monohydride, dibenzyl aluminium monochloride, diphenyl aluminium monochloride, dibenzyl aluminium monobromide, ditolyl aluminium monochloride, diethyl aluminium monoethoxide, diisobutyl aluminium monobutoxide, ethyl aluminium sesquichloride, ethyl aluminium sesquibromide, isobutyl aluminium sesquichloride, ethyl aluminium dichloride, ethyl aluminium dibromide, propyl aluminium dichloride, isobutyl aluminium dichloride, ethyl aluminium diiodide, benzyl aluminium dichloride, benzyl aluminium dibromide, and ethyl aluminium diethoxide.
Claim 15
Dependent Claim
102 words
A method according to claim 9 wherein the compounds expressed by the general formula AlRnX3 n are selected from the group coNsisting of diethyl aluminium monochloride, di-n-propyl aluminium monochloride, diisobutyl aluminium monochloride, di-n-butyl aluminium monochloride, diethyl aluminium monobromide, diethyl aluminium monoiodide, diethyl aluminium monohydride, di-n-propyl aluminium monohydride, diisobutyl aluminium monohydride, dibenzyl aluminium monochloride, diphenyl aluminium monochloride, dibenzyl aluminium monobromide, ditolyl aluminium monochloride, diethyl aluminium monoethoxide, diisobutyl aluminium monobutoxide, ethyl aluminium sesquichloride, ethyl aluminium sesquibromide, isobutyl aluminium sesquichloride, ethyl aluminium dichloride, ethyl aluminium dibromide, propyl aluminium dichloride, isobutyl aluminium dichloride, ethyl aluminium diiodide, benzyl aluminium dichloride, benzyl aluminium dibromide, and ethyl aluminium diethoxide.
Claim 16
Dependent Claim
32 words
A method according to claim 8 wherein the mixture of compounds expressed by the general formula AlR3 and water consists of triethyl aluminium and water mixed in the mol ratio of 1:0.5.
Claim 17
Dependent Claim
32 words
A method according to claim 9 wherein the mixture of compounds expressed by the general formula AlR3 and water consists of triethyl aluminium and water mixed in the mol ratio of 1:0.5.
Claim 18
Dependent Claim
42 words
A method according to claim 4 wherein the compounds of tungsten are selected from the group consisting of tungsten pentachloride, tungsten hexachloride, tungsten pentafluoride, tungsten hexafluoride, tungsten oxytetrachloride, tungsten oxytetrabromide, tungsten oxydichloride, tungsten hexaalcoholate, tungsten hexaphenolate, tetrachlorotungsten diphenolate, tetrachlorotungsten dialcoholate, and Al4W3Cl18.
Claim 19
Dependent Claim
42 words
A method according to claim 5 wherein the compounds of tungsten are selected from the group consisting of tungsten pentachloride, tungsten hexachloride, tungsten pentafluoride, tungsten hexafluoride, tungsten oxytetrachloride, tungsten oxytetrabromide, tungsten oxydichloride, tungsten hexaalcoholate, tungsten hexaphenolate, tetrachlorotungsten diphenolate, tetrachlorotungsten dialcoholate, and Al4W3Cl18.
Claim 20
Dependent Claim
42 words
A method according to claim 4 wherein the compounds of molybdenum are selected from the group consisting of molybdenum pentachloride, molybdenum hexachloride, molybdenum pentafluoride, molybdenum hexafluoride, molybdenum pentabromochloride, molybdenum pentabromide, molybdenum oxytrichloride, molybdenum oxytetrachloride, molybdenum dioxydiacetyl acetonate, dichloromolybdenum dialcoholate, and dichloromolybdenum triphenolate.
Claim 21
Dependent Claim
42 words
A method according to claim 5 wherein the compounds of molybdenum are selected from the group consisting of molybdenum pentachloride, molybdenum hexachloride, molybdenum pentafluoride, molybdenum hexafluoride, molybdenum pentabromochloride, molybdenum pentabromide, molybdenum oxytrichloride, molybdenum oxytetrachloride, molybdenum dioxydiacetyl acetonate, dichloromolybdenum dialcoholate, and dichloromolybdenum triphenolate.
Claim 22
Dependent Claim
38 words
A method according to claim 5 wherein the peroxides are selected from the group consisting of t-butyl peroxide, benzoyl peroxide, t-butyl hydroperoxide, cumene hydroperoxide, hydrogen peroxide, peracetic acid, and esters, ketones and aldehydes all derived from peracetic acid.
Claim 23
Dependent Claim
29 words
A method according to claim 5 wherein the epoxides are selected from the group consisting of ethylene oxide, propylene oxide, butene-1 oxide, epichlorohydrin, allyl glycidyl ethers, and butadiene monoxide.
Claim 24
Dependent Claim
27 words
A method according to claim 5 wherein the organic halides are selected from the group consisting of t-butyl hypoharites, allyl chloride, t-butyl chloride, Alpha -chloroacetone, and 2-chloroethanol.
Claim 25
Dependent Claim
29 words
A method according to claim 5 wherein the acetal compounds are selected from the group consisting of acetaldehyde diethyl acetal, diethoxy methane, acetone dimethyl acetal, and dichloroacetaldehyde dimethyl acetal.
Claim 26
Dependent Claim
29 words
A method according to claim 5 wherein the alcoholic compounds are selected from the group consisting of methyl alcohol, ethyl alcohol, n-propyl alcohol, n-butyl alcohol, isobutyl alcohol, and phenol.
Claim 27
Dependent Claim
23 words
A method according to claim 5 wherein the orthocarboxylic acid esters are selected from the group consisting of orthomethyl formate, and orthoethyl formate.
Claim 28
Dependent Claim
38 words
A method according to claim 6 wherein the organic solvents are selected from the group consisting of pentane, hexane, petroleum ethers, decane, benzene, toluene, xylene, cyclohexane, decalin, cyclooctane, methylene chloride, 1,2-dichloroethane, 1, 2-dichloropropane, chloroform, chlorobenzene, and carbon tetrachloride.
Claim 29
Dependent Claim
38 words
A method according to claim 7 wherein the organic solvents are selected from the group consisting of pentane, heptane, hexane, petroleum ethers, decane, benzene, toluene, xylene, cyclohexane, decalin, cyclooctane, methylene chloride, 1,2-dichloroethane, 1,2-dichloropropane, chloroform, chlorobenzene, and carbon tetrachloride.
Claim 30
Dependent Claim
34 words
A method according to claim 4 which comprises further adding to the reaction system a molecular weight controlling agent selected from the group consisting of Alpha -olefins, internal olefins, conjugate diolefins, and nonconjugate diolefins.
Claim 31
Dependent Claim
34 words
A method according to claim 5 which comprises further adding to the reaction system a molecular weight controlling agent selected from the group consisting of Alpha -olefins, internal olefins, conjugate diolefins, and nonconjugate diolefins.
Claim 32
Dependent Claim
21 words
A method according to claim 4 wherein the ring-opening polymerization is carried out at a temperature ranging from -100*C to +200*C.
Claim 33
Dependent Claim
21 words
A method according to claim 5 wherein the ring-opening polymerization is carried out at a temperature ranging from -100*C to +200*C.
References Cited (Backward Citations)
US2721189A
Cited
US2932630A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1977-12-23 | 1978-06-24 | 1978-12-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1981-12-23 | 1982-06-24 | 1982-12-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1985-12-23 | 1986-06-24 | 1986-12-24 | $7700.00 | Window Closed / Lapsed |