DE2437104A1 - Verfahren zur herstellung von cyclopenten-copolymeren - Google Patents
Verfahren zur herstellung von cyclopenten-copolymerenInfo
- Publication number
- DE2437104A1 DE2437104A1 DE2437104A DE2437104A DE2437104A1 DE 2437104 A1 DE2437104 A1 DE 2437104A1 DE 2437104 A DE2437104 A DE 2437104A DE 2437104 A DE2437104 A DE 2437104A DE 2437104 A1 DE2437104 A1 DE 2437104A1
- Authority
- DE
- Germany
- Prior art keywords
- polymerization
- cyclopentene
- catalyst
- copolymer
- tungsten
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 39
- 229920001577 copolymer Polymers 0.000 title claims description 36
- 230000008569 process Effects 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentenylidene Natural products C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 title description 67
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 title description 36
- 239000003054 catalyst Substances 0.000 claims description 34
- 238000006116 polymerization reaction Methods 0.000 claims description 34
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 23
- 229910052721 tungsten Inorganic materials 0.000 claims description 23
- 239000010937 tungsten Substances 0.000 claims description 23
- -1 polycyclic olefin Chemical class 0.000 claims description 15
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 12
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 7
- 239000012442 inert solvent Substances 0.000 claims description 7
- 229910052750 molybdenum Inorganic materials 0.000 claims description 7
- 239000011733 molybdenum Substances 0.000 claims description 7
- 229910000765 intermetallic Inorganic materials 0.000 claims description 3
- 150000005673 monoalkenes Chemical class 0.000 claims description 3
- 150000002902 organometallic compounds Chemical class 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 23
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- 229920001519 homopolymer Polymers 0.000 description 19
- 229920000642 polymer Polymers 0.000 description 19
- 238000007334 copolymerization reaction Methods 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 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 description 14
- 229920001971 elastomer Polymers 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000005060 rubber Substances 0.000 description 7
- 239000000806 elastomer Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 238000007086 side reaction Methods 0.000 description 5
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
- 230000003712 anti-aging effect Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000001941 cyclopentenes Chemical class 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 229920003246 polypentenamer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 238000006462 rearrangement reaction Methods 0.000 description 2
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229910001930 tungsten oxide Inorganic materials 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000006237 Intermediate SAF Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000010692 aromatic oil Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 150000002901 organomagnesium compounds Chemical class 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP48086502A JPS5034699A (enExample) | 1973-07-31 | 1973-07-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2437104A1 true DE2437104A1 (de) | 1975-02-20 |
Family
ID=13888741
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2437104A Pending DE2437104A1 (de) | 1973-07-31 | 1974-07-30 | Verfahren zur herstellung von cyclopenten-copolymeren |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3941757A (enExample) |
| JP (1) | JPS5034699A (enExample) |
| DE (1) | DE2437104A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4262103A (en) * | 1977-12-05 | 1981-04-14 | The B. F. Goodrich Company | Hydrocarbon-soluble copolymers of bicycloheptenes and 1,3-butadiene |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4138448A (en) * | 1977-12-05 | 1979-02-06 | The B. F. Goodrich Company | Process for preparing polymers of cyclopentadiene and bicycloheptene mixtures |
| US4239874A (en) * | 1979-02-21 | 1980-12-16 | The Goodyear Tire & Rubber Company | Cyclopentene copolymerization process |
| JPS5763349A (en) * | 1980-10-03 | 1982-04-16 | Kanegafuchi Chem Ind Co Ltd | Composition |
| RU2453566C2 (ru) * | 2006-10-17 | 2012-06-20 | Файэрстоун Полимерс, Ллк | Эластомеры, способы их получения и их использование |
| JP6390609B2 (ja) | 2013-02-26 | 2018-09-19 | 日本ゼオン株式会社 | シクロペンテン開環共重合体、その製造方法およびゴム組成物 |
| EP3822317B1 (en) * | 2018-07-13 | 2025-02-26 | Zeon Corporation | Ring-opening copolymer composition |
| 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 |
| WO2021188337A1 (en) | 2020-03-19 | 2021-09-23 | Exxonmobil Chemical Patents Inc. | Pentavalent dimeric group 6 transition metal complexes and methods for use thereof |
| JP2023518292A (ja) | 2020-03-19 | 2023-04-28 | 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 | 環状オレフィン重合のための改善された開環メタセシス触媒系 |
| US11912861B2 (en) | 2020-10-29 | 2024-02-27 | ExxonMobil Engineering & Technology Co. | Rubber composition for lighter weight tires and improved wet traction |
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 |
| BE755884A (fr) * | 1969-09-08 | 1971-02-15 | Huels Chemische Werke Ag | Polyalkenameres et procede pour les preparer |
| DE2105161C3 (de) * | 1971-02-04 | 1978-06-08 | Chemische Werke Huels Ag, 4370 Marl | Verfahren zur Herstellung von flussigen Polybutenameren |
| BE787030A (fr) * | 1971-08-02 | 1973-02-01 | Montedison Spa | Copolyalcenameres ayant une structure sequentielle et procede pour les preparer |
| US3772255A (en) * | 1972-06-07 | 1973-11-13 | Goodyear Tire & Rubber | Ring-opening polymerization of cycloolefins |
-
1973
- 1973-07-31 JP JP48086502A patent/JPS5034699A/ja active Pending
-
1974
- 1974-07-30 DE DE2437104A patent/DE2437104A1/de active Pending
- 1974-07-31 US US05/493,387 patent/US3941757A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4262103A (en) * | 1977-12-05 | 1981-04-14 | The B. F. Goodrich Company | Hydrocarbon-soluble copolymers of bicycloheptenes and 1,3-butadiene |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5034699A (enExample) | 1975-04-03 |
| US3941757A (en) | 1976-03-02 |
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