DE2334604A1 - Polymerisation von cycloocten - Google Patents
Polymerisation von cyclooctenInfo
- Publication number
- DE2334604A1 DE2334604A1 DE19732334604 DE2334604A DE2334604A1 DE 2334604 A1 DE2334604 A1 DE 2334604A1 DE 19732334604 DE19732334604 DE 19732334604 DE 2334604 A DE2334604 A DE 2334604A DE 2334604 A1 DE2334604 A1 DE 2334604A1
- Authority
- DE
- Germany
- Prior art keywords
- cis
- polyoctenamers
- polymerization
- cyclooctene
- double bonds
- 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
- 238000006116 polymerization reaction Methods 0.000 title description 9
- URYYVOIYTNXXBN-UHFFFAOYSA-N cyclooctene Chemical compound [CH]1[CH]CCCCCC1 URYYVOIYTNXXBN-UHFFFAOYSA-N 0.000 title 1
- 229920003245 polyoctenamer Polymers 0.000 claims description 13
- 239000004913 cyclooctene Substances 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- -1 cyclic olefin Chemical class 0.000 claims description 9
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 claims description 9
- 229910052721 tungsten Inorganic materials 0.000 claims description 9
- 239000010937 tungsten Substances 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 5
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- 150000003944 halohydrins Chemical class 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 4
- 229910015900 BF3 Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 150000002902 organometallic compounds Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000009477 glass transition Effects 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 3
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- VZIQXGLTRZLBEX-UHFFFAOYSA-N 2-chloro-1-propanol Chemical compound CC(Cl)CO VZIQXGLTRZLBEX-UHFFFAOYSA-N 0.000 description 1
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- UCIYGNATMHQYCT-OWOJBTEDSA-N cyclodecene Chemical compound C1CCCC\C=C\CCC1 UCIYGNATMHQYCT-OWOJBTEDSA-N 0.000 description 1
- ZOLLIQAKMYWTBR-RYMQXAEESA-N cyclododecatriene Chemical compound C/1C\C=C\CC\C=C/CC\C=C\1 ZOLLIQAKMYWTBR-RYMQXAEESA-N 0.000 description 1
- HYPABJGVBDSCIT-UPHRSURJSA-N cyclododecene Chemical compound C1CCCCC\C=C/CCCC1 HYPABJGVBDSCIT-UPHRSURJSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
- Polymerization Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732334604 DE2334604A1 (de) | 1973-07-07 | 1973-07-07 | Polymerisation von cycloocten |
| US05/485,294 US3939136A (en) | 1973-07-07 | 1974-07-02 | Polymerisation of cyclooctene |
| GB2945874A GB1469149A (en) | 1973-07-07 | 1974-07-03 | Polymerisation of cyclooctene |
| JP49076566A JPS5039398A (OSRAM) | 1973-07-07 | 1974-07-05 | |
| NL7409164A NL7409164A (nl) | 1973-07-07 | 1974-07-05 | Werkwijze voor het polymeriseren van cyclooecteen. |
| AT554874A AT327549B (de) | 1973-07-07 | 1974-07-05 | Verfahren zur herstellung von polyoctenameren |
| FR7423550A FR2235959B1 (OSRAM) | 1973-07-07 | 1974-07-05 | |
| BE146251A BE817292A (fr) | 1973-07-07 | 1974-07-05 | Polymerisation du cyclooctene |
| IT51935/74A IT1016316B (it) | 1973-07-07 | 1974-07-05 | Poliottenameri e procedimento per la loro produzione |
| CA204,173A CA1023497A (en) | 1973-07-07 | 1974-07-05 | Polymerisation of cyclooctene |
| ES428034A ES428034A1 (es) | 1973-07-07 | 1974-07-06 | Procedimiento para la obtencion de un polioctenamero. |
| AU71421/74A AU488815B2 (en) | 1974-07-19 | Polymerisatin of cyclooctene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732334604 DE2334604A1 (de) | 1973-07-07 | 1973-07-07 | Polymerisation von cycloocten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2334604A1 true DE2334604A1 (de) | 1975-01-30 |
Family
ID=5886218
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732334604 Pending DE2334604A1 (de) | 1973-07-07 | 1973-07-07 | Polymerisation von cycloocten |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3939136A (OSRAM) |
| JP (1) | JPS5039398A (OSRAM) |
| AT (1) | AT327549B (OSRAM) |
| BE (1) | BE817292A (OSRAM) |
| CA (1) | CA1023497A (OSRAM) |
| DE (1) | DE2334604A1 (OSRAM) |
| ES (1) | ES428034A1 (OSRAM) |
| FR (1) | FR2235959B1 (OSRAM) |
| GB (1) | GB1469149A (OSRAM) |
| IT (1) | IT1016316B (OSRAM) |
| NL (1) | NL7409164A (OSRAM) |
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 (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0129474B1 (fr) * | 1983-06-15 | 1986-04-23 | Societe Nationale Elf Aquitaine | Catalyseur perfectionné pour la métathèse d'oléfines |
| JPS63135238A (ja) * | 1986-11-28 | 1988-06-07 | ダイセル・ヒユルス株式会社 | 振動減衰性複合金属板 |
| JPS63209834A (ja) * | 1987-02-25 | 1988-08-31 | ダイセル・ヒユルス株式会社 | 軽量複合金属板 |
| US5369195A (en) * | 1988-11-30 | 1994-11-29 | Shell Oil Company | Polymerization of cyclic olefins |
| US5254629A (en) * | 1988-11-30 | 1993-10-19 | Shell Oil Company | Polymerization of cyclic olefins |
| DE102010030510A1 (de) * | 2010-06-25 | 2011-12-29 | Evonik Degussa Gmbh | Verfahren zur Herstellung von flüssigem und farblosem Polyoctenamer durch ringöffnende, metathetische Polymerisation von Cycloocten |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL144291B (nl) * | 1965-02-11 | 1974-12-16 | Montedison Spa | Werkwijze om lineaire homopolymeren van cycloalkenen te bereiden. |
| DE2106302C3 (de) * | 1971-02-10 | 1979-06-07 | Bayer Ag, 5090 Leverkusen | Verfahren zur Polymerisation von acyclischen Verbindungen |
-
1973
- 1973-07-07 DE DE19732334604 patent/DE2334604A1/de active Pending
-
1974
- 1974-07-02 US US05/485,294 patent/US3939136A/en not_active Expired - Lifetime
- 1974-07-03 GB GB2945874A patent/GB1469149A/en not_active Expired
- 1974-07-05 NL NL7409164A patent/NL7409164A/xx not_active Application Discontinuation
- 1974-07-05 IT IT51935/74A patent/IT1016316B/it active
- 1974-07-05 BE BE146251A patent/BE817292A/xx unknown
- 1974-07-05 CA CA204,173A patent/CA1023497A/en not_active Expired
- 1974-07-05 FR FR7423550A patent/FR2235959B1/fr not_active Expired
- 1974-07-05 JP JP49076566A patent/JPS5039398A/ja active Pending
- 1974-07-05 AT AT554874A patent/AT327549B/de not_active IP Right Cessation
- 1974-07-06 ES ES428034A patent/ES428034A1/es 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 |
|---|---|
| FR2235959B1 (OSRAM) | 1978-03-24 |
| AT327549B (de) | 1976-02-10 |
| GB1469149A (en) | 1977-03-30 |
| AU7142174A (en) | 1976-01-22 |
| ATA554874A (de) | 1975-04-15 |
| IT1016316B (it) | 1977-05-30 |
| US3939136A (en) | 1976-02-17 |
| ES428034A1 (es) | 1976-09-01 |
| FR2235959A1 (OSRAM) | 1975-01-31 |
| BE817292A (fr) | 1975-01-06 |
| NL7409164A (nl) | 1975-01-09 |
| JPS5039398A (OSRAM) | 1975-04-11 |
| CA1023497A (en) | 1977-12-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |