DE2332565A1 - Verfahren zur polymerisation von cyclooctadien-(1,5) - Google Patents
Verfahren zur polymerisation von cyclooctadien-(1,5)Info
- Publication number
- DE2332565A1 DE2332565A1 DE2332565A DE2332565A DE2332565A1 DE 2332565 A1 DE2332565 A1 DE 2332565A1 DE 2332565 A DE2332565 A DE 2332565A DE 2332565 A DE2332565 A DE 2332565A DE 2332565 A1 DE2332565 A1 DE 2332565A1
- Authority
- DE
- Germany
- Prior art keywords
- polymerization
- content
- toluene
- double bonds
- cyclooctadiene
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 16
- 238000006116 polymerization reaction Methods 0.000 title description 17
- -1 aluminum halide Chemical class 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 12
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 claims description 8
- 229910052782 aluminium Inorganic materials 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000002118 epoxides Chemical class 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000003657 tungsten Chemical class 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000003944 halohydrins Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- 239000000460 chlorine Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 150000003658 tungsten compounds Chemical class 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 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
- 229920001971 elastomer Polymers 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002589 poly(vinylethylene) polymer Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000010057 rubber processing Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 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
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
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2332565A DE2332565A1 (de) | 1973-06-27 | 1973-06-27 | Verfahren zur polymerisation von cyclooctadien-(1,5) |
| US05/481,208 US3933778A (en) | 1973-06-27 | 1974-06-20 | Process for the polymerisation of cyclooctadiene |
| IT51682/74A IT1016143B (it) | 1973-06-27 | 1974-06-24 | Procedimento per polimerizzare cicloottadiene 1 5 |
| CA203,193A CA1025595A (en) | 1973-06-27 | 1974-06-24 | Process for the polymerisation of cyclooctadiene-(1,5) |
| NL7408470A NL7408470A (enExample) | 1973-06-27 | 1974-06-24 | |
| AT526274A AT326352B (de) | 1973-06-27 | 1974-06-25 | Verfahren zur ringöffnenden polymerisation von cyclooctadien-(1,5) |
| JP49071937A JPS5038799A (enExample) | 1973-06-27 | 1974-06-25 | |
| GB2833474A GB1433573A (en) | 1973-06-27 | 1974-06-26 | Process for the polymerisation of cycloocta-1,5-diene |
| ES427702A ES427702A1 (es) | 1973-06-27 | 1974-06-26 | Procedimiento para la obtencion de polioctadienameros. |
| BE145905A BE816885A (fr) | 1973-06-27 | 1974-06-26 | Procede de polymerisation du cyclooctadiene-(1,5) |
| AU70503/74A AU482679B2 (en) | 1973-06-27 | 1974-06-26 | Process forthe polymerisation of cyclooctadiene (1, 5 |
| FR7422504A FR2235149B1 (enExample) | 1973-06-27 | 1974-06-27 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2332565A DE2332565A1 (de) | 1973-06-27 | 1973-06-27 | Verfahren zur polymerisation von cyclooctadien-(1,5) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2332565A1 true DE2332565A1 (de) | 1975-01-16 |
Family
ID=5885168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2332565A Withdrawn DE2332565A1 (de) | 1973-06-27 | 1973-06-27 | Verfahren zur polymerisation von cyclooctadien-(1,5) |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3933778A (enExample) |
| JP (1) | JPS5038799A (enExample) |
| AT (1) | AT326352B (enExample) |
| BE (1) | BE816885A (enExample) |
| CA (1) | CA1025595A (enExample) |
| DE (1) | DE2332565A1 (enExample) |
| ES (1) | ES427702A1 (enExample) |
| FR (1) | FR2235149B1 (enExample) |
| GB (1) | GB1433573A (enExample) |
| IT (1) | IT1016143B (enExample) |
| NL (1) | NL7408470A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2552616A1 (de) * | 1975-11-24 | 1977-06-02 | Goodyear Tire & Rubber | Verfahren zur herstellung von polyalkenameren mit hohem cis-gehalt |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5143992A (en) * | 1991-07-12 | 1992-09-01 | Shell Oil Company | Methathesis polymerizable adducts of a divinylcyclohydrocarbon and cyclopentadiene |
| US5218065A (en) * | 1991-08-30 | 1993-06-08 | Shell Oil Company | Polymerization process |
| US5278305A (en) * | 1992-12-31 | 1994-01-11 | Shell Oil Company | Catalysts for ring-opening, metathesis polymerization of cyclic olefins |
| US5276118A (en) * | 1992-12-31 | 1994-01-04 | Shell Oil Company | Diaryl carbinol metathesis catalysts for ring-opening polymerization of cyclic olefins |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1915684A1 (de) * | 1969-03-27 | 1970-10-08 | Bayer Ag | Polymerisate von Cyclopenten |
| BE758130A (fr) * | 1969-10-28 | 1970-04-01 | Bayer Ag | Procede de preparation de polymeres greffes et produits obtenuspar ce procede |
| US3657208A (en) * | 1970-11-02 | 1972-04-18 | Goodyear Tire & Rubber | Ternary catalyst systems for the polymerization of cyclic olefins |
| DE2056178A1 (de) * | 1970-11-14 | 1972-05-25 | Bayer | trans-1,5 Polypentenamer mit verbesserten Verarbeitungseigenschaften |
| NO137551C (no) * | 1970-12-16 | 1978-03-15 | Montedison Spa | Fremgangsmaate for polymerisering av cyclopenten og/eller cycloocten |
-
1973
- 1973-06-27 DE DE2332565A patent/DE2332565A1/de not_active Withdrawn
-
1974
- 1974-06-20 US US05/481,208 patent/US3933778A/en not_active Expired - Lifetime
- 1974-06-24 IT IT51682/74A patent/IT1016143B/it active
- 1974-06-24 NL NL7408470A patent/NL7408470A/xx not_active Application Discontinuation
- 1974-06-24 CA CA203,193A patent/CA1025595A/en not_active Expired
- 1974-06-25 AT AT526274A patent/AT326352B/de not_active IP Right Cessation
- 1974-06-25 JP JP49071937A patent/JPS5038799A/ja active Pending
- 1974-06-26 ES ES427702A patent/ES427702A1/es not_active Expired
- 1974-06-26 BE BE145905A patent/BE816885A/xx unknown
- 1974-06-26 GB GB2833474A patent/GB1433573A/en not_active Expired
- 1974-06-27 FR FR7422504A patent/FR2235149B1/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2552616A1 (de) * | 1975-11-24 | 1977-06-02 | Goodyear Tire & Rubber | Verfahren zur herstellung von polyalkenameren mit hohem cis-gehalt |
Also Published As
| Publication number | Publication date |
|---|---|
| BE816885A (fr) | 1974-12-27 |
| GB1433573A (en) | 1976-04-28 |
| ES427702A1 (es) | 1976-08-01 |
| ATA526274A (de) | 1975-02-15 |
| US3933778A (en) | 1976-01-20 |
| AU7050374A (en) | 1976-01-08 |
| FR2235149A1 (enExample) | 1975-01-24 |
| JPS5038799A (enExample) | 1975-04-10 |
| FR2235149B1 (enExample) | 1978-01-13 |
| IT1016143B (it) | 1977-05-30 |
| AT326352B (de) | 1975-12-10 |
| NL7408470A (enExample) | 1974-12-31 |
| CA1025595A (en) | 1978-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8126 | Change of the secondary classification | ||
| 8130 | Withdrawal |