DE1961865C3 - Copolymerisation von cyclischen Monoolefinen mit cyclischen Polyolefinen - Google Patents
Copolymerisation von cyclischen Monoolefinen mit cyclischen PolyolefinenInfo
- Publication number
- DE1961865C3 DE1961865C3 DE1961865A DE1961865A DE1961865C3 DE 1961865 C3 DE1961865 C3 DE 1961865C3 DE 1961865 A DE1961865 A DE 1961865A DE 1961865 A DE1961865 A DE 1961865A DE 1961865 C3 DE1961865 C3 DE 1961865C3
- Authority
- DE
- Germany
- Prior art keywords
- cyclic
- tungsten
- polyolefins
- catalyst
- polymerization
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229920000098 polyolefin Polymers 0.000 title claims description 15
- 125000004122 cyclic group Chemical group 0.000 title claims description 10
- 150000005675 cyclic monoalkenes Chemical class 0.000 title claims description 6
- 238000007334 copolymerization reaction Methods 0.000 title description 6
- 229910052721 tungsten Inorganic materials 0.000 claims description 28
- 239000010937 tungsten Substances 0.000 claims description 28
- -1 tungsten halogen compound Chemical class 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 22
- 238000006116 polymerization reaction Methods 0.000 claims description 15
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 4
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 4
- 150000008282 halocarbons Chemical class 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- ZOLLIQAKMYWTBR-MOLCZBCNSA-N (1z,5z,9z)-cyclododeca-1,5,9-triene Chemical compound C\1C\C=C/CC\C=C/CC\C=C/1 ZOLLIQAKMYWTBR-MOLCZBCNSA-N 0.000 claims description 2
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 claims description 2
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 claims description 2
- NYEWDMNOXFGGDX-UHFFFAOYSA-N 2-chlorocyclohexan-1-ol Chemical compound OC1CCCCC1Cl NYEWDMNOXFGGDX-UHFFFAOYSA-N 0.000 claims description 2
- QSECPQCFCWVBKM-UHFFFAOYSA-N 2-iodoethanol Chemical compound OCCI QSECPQCFCWVBKM-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000002524 organometallic group Chemical group 0.000 claims 2
- MCCNFMGRUXKBFV-UHFFFAOYSA-N 2-chlorocyclopentan-1-ol Chemical compound OC1CCCC1Cl MCCNFMGRUXKBFV-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 35
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 17
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 8
- 150000002924 oxiranes Chemical class 0.000 description 8
- 229910052736 halogen Inorganic materials 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 230000007717 exclusion Effects 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000012084 conversion product Substances 0.000 description 3
- 150000001925 cycloalkenes Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 238000007142 ring opening reaction Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 150000003658 tungsten compounds Chemical class 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229950011008 tetrachloroethylene Drugs 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- GICIECWTEWJCRE-UHFFFAOYSA-N 3,4,4,7-tetramethyl-2,3-dihydro-1h-naphthalene Chemical compound CC1=CC=C2C(C)(C)C(C)CCC2=C1 GICIECWTEWJCRE-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- UCIYGNATMHQYCT-OWOJBTEDSA-N cyclodecene Chemical compound C1CCCC\C=C\CCC1 UCIYGNATMHQYCT-OWOJBTEDSA-N 0.000 description 1
- AWSUTSRUDKEWIO-UHFFFAOYSA-N cyclooctadecene Chemical compound C1CCCCCCCCC=CCCCCCCC1 AWSUTSRUDKEWIO-UHFFFAOYSA-N 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 239000004913 cyclooctene Substances 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- UCAOGXRUJFKQAP-UHFFFAOYSA-N n,n-dimethyl-5-nitropyridin-2-amine Chemical compound CN(C)C1=CC=C([N+]([O-])=O)C=N1 UCAOGXRUJFKQAP-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
- C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1961865A DE1961865C3 (de) | 1969-12-10 | 1969-12-10 | Copolymerisation von cyclischen Monoolefinen mit cyclischen Polyolefinen |
| GB5457870A GB1324108A (en) | 1969-12-10 | 1970-11-17 | Copolymerisation of cyclomono olefins with non-conjugated cyclic polyolefines |
| CA099270A CA931691A (en) | 1969-12-10 | 1970-11-27 | Copolymerisation of cyclopentene with polycyclic polyolefines |
| JP45108598A JPS4826399B1 (enExample) | 1969-12-10 | 1970-12-09 | |
| FR7044550A FR2070802B1 (enExample) | 1969-12-10 | 1970-12-10 | |
| NL7018069.A NL162672C (nl) | 1969-12-10 | 1970-12-10 | Werkwijze voor de copolymerisatie van ten minste een cy- clisch monoalkeen en ten minste een cyclisch polyalkeen. |
| BE760149A BE760149A (fr) | 1969-12-10 | 1970-12-10 | Copolymerisation du cyclopentene avec des olefines polycycliques |
| ES386316A ES386316A1 (es) | 1969-12-10 | 1970-12-10 | Procedimiento para la copolimerizacion de al menos una mo- noolefina ciclica y al menos una poliolefina ciclica. |
| US00204372A US3781257A (en) | 1969-12-10 | 1971-12-02 | Copolymerization of cyclopentene with polycyclic polyolefines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1961865A DE1961865C3 (de) | 1969-12-10 | 1969-12-10 | Copolymerisation von cyclischen Monoolefinen mit cyclischen Polyolefinen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1961865A1 DE1961865A1 (de) | 1971-06-16 |
| DE1961865B2 DE1961865B2 (de) | 1979-09-20 |
| DE1961865C3 true DE1961865C3 (de) | 1980-06-12 |
Family
ID=5753441
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1961865A Expired DE1961865C3 (de) | 1969-12-10 | 1969-12-10 | Copolymerisation von cyclischen Monoolefinen mit cyclischen Polyolefinen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3781257A (enExample) |
| JP (1) | JPS4826399B1 (enExample) |
| BE (1) | BE760149A (enExample) |
| CA (1) | CA931691A (enExample) |
| DE (1) | DE1961865C3 (enExample) |
| ES (1) | ES386316A1 (enExample) |
| FR (1) | FR2070802B1 (enExample) |
| GB (1) | GB1324108A (enExample) |
| NL (1) | NL162672C (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3867361A (en) * | 1966-03-28 | 1975-02-18 | Goodyear Tire & Rubber | A process for the polymerization of cyclic olefins |
| US3974094A (en) * | 1970-06-11 | 1976-08-10 | Chemische Werke Huls Aktiengesellschaft | Catalyst system for the production of polyalkenamers |
| IT948018B (it) * | 1971-03-01 | 1973-05-30 | Ici Ltd | Processo per la produzione di polimeri |
| US4046710A (en) * | 1973-06-27 | 1977-09-06 | Bayer Aktiengesellschaft | Polymerization of cyclic olefins |
| US3859263A (en) * | 1973-07-27 | 1975-01-07 | Goodyear Tire & Rubber | Preparation of unsaturated copolymers |
| GB1553673A (en) * | 1975-07-30 | 1979-09-26 | Bp Chem Int Ltd | Polymerisation catalyst |
| US4136249A (en) * | 1977-12-05 | 1979-01-23 | The B. F. Goodrich Company | Ring-opened copolymers of dihydrodiclopentadiene, norbornene or alkylnorbornene, and acyclic olefin |
| DE3568176D1 (en) * | 1984-11-16 | 1989-03-16 | Hercules Inc | Catalyst composition for polymerization of cycloolefins |
| US5011730A (en) * | 1987-08-14 | 1991-04-30 | The B. F. Goodrich Company | Bulk polymerized cycloolefin circuit boards |
| US4899005A (en) * | 1987-11-19 | 1990-02-06 | The B. F. Goodrich Company | Method for preparing cycloolefin copolymers with improved heat stability |
| US4843185A (en) * | 1988-04-08 | 1989-06-27 | The B. F. Goodrich Company | Method for enhancing the polymerization activity of crude cycloolefin monomers for bulk polymerization |
| US4943621A (en) * | 1988-08-04 | 1990-07-24 | The B. F. Goodrich Company | Storage stable components of reactive formulations for bulk polymerization of cycloolefin monomers |
| FR2650760B1 (fr) * | 1989-08-08 | 1991-10-31 | Inst Francais Du Petrole | Nouvelle composition catalytique et sa mise en oeuvre pour l'oligomerisation des monoolefines |
| WO2018173968A1 (ja) * | 2017-03-24 | 2018-09-27 | 日本ゼオン株式会社 | シクロペンテン開環共重合体及びその製造方法 |
| WO2021113503A1 (en) * | 2019-12-04 | 2021-06-10 | Exxonmobil Chemical Patents Inc. | Polymers prepared by ring opening metathesis polymerization |
| JP2023516712A (ja) * | 2020-03-03 | 2023-04-20 | エクソンモービル ケミカル パテンツ インコーポレイテッド | 大型トラックおよびバスタイヤトレッドのためのゴム配合物ならびにそれに関する方法 |
| JP2023516400A (ja) * | 2020-03-03 | 2023-04-19 | エクソンモービル ケミカル パテンツ インコーポレイテッド | パッセンジャータイヤトレッドのためのゴム配合物およびそれに関する方法 |
-
1969
- 1969-12-10 DE DE1961865A patent/DE1961865C3/de not_active Expired
-
1970
- 1970-11-17 GB GB5457870A patent/GB1324108A/en not_active Expired
- 1970-11-27 CA CA099270A patent/CA931691A/en not_active Expired
- 1970-12-09 JP JP45108598A patent/JPS4826399B1/ja active Pending
- 1970-12-10 BE BE760149A patent/BE760149A/xx unknown
- 1970-12-10 NL NL7018069.A patent/NL162672C/xx not_active IP Right Cessation
- 1970-12-10 ES ES386316A patent/ES386316A1/es not_active Expired
- 1970-12-10 FR FR7044550A patent/FR2070802B1/fr not_active Expired
-
1971
- 1971-12-02 US US00204372A patent/US3781257A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE1961865A1 (de) | 1971-06-16 |
| NL162672B (nl) | 1980-01-15 |
| FR2070802B1 (enExample) | 1977-01-21 |
| NL7018069A (enExample) | 1971-06-14 |
| FR2070802A1 (enExample) | 1971-09-17 |
| JPS4826399B1 (enExample) | 1973-08-09 |
| US3781257A (en) | 1973-12-25 |
| ES386316A1 (es) | 1973-03-16 |
| NL162672C (nl) | 1980-06-16 |
| CA931691A (en) | 1973-08-07 |
| GB1324108A (en) | 1973-07-18 |
| DE1961865B2 (de) | 1979-09-20 |
| BE760149A (fr) | 1971-05-17 |
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