DE1920500A1 - Katalysator fuer die ringoeffnende Polymerisation von Cyclopenten - Google Patents
Katalysator fuer die ringoeffnende Polymerisation von CyclopentenInfo
- Publication number
- DE1920500A1 DE1920500A1 DE19691920500 DE1920500A DE1920500A1 DE 1920500 A1 DE1920500 A1 DE 1920500A1 DE 19691920500 DE19691920500 DE 19691920500 DE 1920500 A DE1920500 A DE 1920500A DE 1920500 A1 DE1920500 A1 DE 1920500A1
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- cyclopentene
- solution
- tungsten
- 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.)
- Pending
Links
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 title claims description 26
- 239000003054 catalyst Substances 0.000 title claims description 18
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 title claims description 13
- 238000007151 ring opening polymerisation reaction Methods 0.000 title description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 8
- KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 4
- YOUIDGQAIILFBW-UHFFFAOYSA-J tetrachlorotungsten Chemical compound Cl[W](Cl)(Cl)Cl YOUIDGQAIILFBW-UHFFFAOYSA-J 0.000 claims description 4
- 238000007142 ring opening reaction Methods 0.000 claims description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims 1
- 238000007334 copolymerization reaction Methods 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 8
- 238000000034 method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- -1 polycyclic olefins Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 2
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 2
- 229920003246 polypentenamer Polymers 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 229950011008 tetrachloroethylene Drugs 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 2
- 150000003658 tungsten compounds Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- 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 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
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-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
- WXLHSHWRIUJYSN-UHFFFAOYSA-N CC1=CC=CC=C1.Cl.Cl.Cl.Cl.Cl.Cl Chemical compound CC1=CC=CC=C1.Cl.Cl.Cl.Cl.Cl.Cl WXLHSHWRIUJYSN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 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
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-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
- 150000001993 dienes Chemical class 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002927 oxygen compounds Chemical class 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- 150000003657 tungsten Chemical class 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691920500 DE1920500A1 (de) | 1969-04-23 | 1969-04-23 | Katalysator fuer die ringoeffnende Polymerisation von Cyclopenten |
| CA080373A CA922301A (en) | 1969-04-23 | 1970-04-17 | Catalyst for the ring opening polymerisation of cyclopentene |
| AT362670A AT298793B (de) | 1969-04-23 | 1970-04-21 | Verfahren zur ringöffnenden Homo- oder Copolymerisation von Cyclopenten |
| NL7005768A NL7005768A (enrdf_load_stackoverflow) | 1969-04-23 | 1970-04-21 | |
| GB1256650D GB1256650A (enrdf_load_stackoverflow) | 1969-04-23 | 1970-04-22 | |
| ES378900A ES378900A1 (es) | 1969-04-23 | 1970-04-22 | Procedimiento de obtencion de catalizadores para la homo y copolimerizacion de ciclopenteno con apertura de anillo. |
| BE749406D BE749406A (fr) | 1969-04-23 | 1970-04-23 | Catalyseur pour la polymerisation avec ouverture du cycle du cyclopentene |
| FR7014894A FR2046441A5 (enrdf_load_stackoverflow) | 1969-04-23 | 1970-04-23 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691920500 DE1920500A1 (de) | 1969-04-23 | 1969-04-23 | Katalysator fuer die ringoeffnende Polymerisation von Cyclopenten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1920500A1 true DE1920500A1 (de) | 1970-11-05 |
Family
ID=5731985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691920500 Pending DE1920500A1 (de) | 1969-04-23 | 1969-04-23 | Katalysator fuer die ringoeffnende Polymerisation von Cyclopenten |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT298793B (enrdf_load_stackoverflow) |
| BE (1) | BE749406A (enrdf_load_stackoverflow) |
| CA (1) | CA922301A (enrdf_load_stackoverflow) |
| DE (1) | DE1920500A1 (enrdf_load_stackoverflow) |
| ES (1) | ES378900A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2046441A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1256650A (enrdf_load_stackoverflow) |
| NL (1) | NL7005768A (enrdf_load_stackoverflow) |
-
1969
- 1969-04-23 DE DE19691920500 patent/DE1920500A1/de active Pending
-
1970
- 1970-04-17 CA CA080373A patent/CA922301A/en not_active Expired
- 1970-04-21 AT AT362670A patent/AT298793B/de not_active IP Right Cessation
- 1970-04-21 NL NL7005768A patent/NL7005768A/xx unknown
- 1970-04-22 ES ES378900A patent/ES378900A1/es not_active Expired
- 1970-04-22 GB GB1256650D patent/GB1256650A/en not_active Expired
- 1970-04-23 FR FR7014894A patent/FR2046441A5/fr not_active Expired
- 1970-04-23 BE BE749406D patent/BE749406A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1256650A (enrdf_load_stackoverflow) | 1971-12-08 |
| BE749406A (fr) | 1970-10-01 |
| AT298793B (de) | 1972-05-25 |
| CA922301A (en) | 1973-03-06 |
| ES378900A1 (es) | 1972-08-01 |
| FR2046441A5 (enrdf_load_stackoverflow) | 1971-03-05 |
| NL7005768A (enrdf_load_stackoverflow) | 1970-10-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Calderon et al. | Ring‐opening polymerization of unsaturated alicyclic compounds | |
| DE69025144T2 (de) | Hydrogenierte, durch Ringöffnung erhaltene Polymere und Verfahren zu ihrer Herstellung | |
| US3631010A (en) | Process for the production of transpolypentenamers | |
| Gaylord et al. | Poly-2, 3-and 2, 7-Bicyclo [2.2. 1] hept-2-enes: Preparation and Structures of Polynorbornenes | |
| US3459725A (en) | High molecular weight unsaturated hydrocarbon homopolymers and process for preparing them | |
| DE1961865C3 (de) | Copolymerisation von cyclischen Monoolefinen mit cyclischen Polyolefinen | |
| DE2028935A1 (de) | Polyalkenamere und Verfahren zu deren Herstellung | |
| US3549607A (en) | High cis polypentenamers | |
| US3707520A (en) | Polymers of cyclopentene obtained by polymerizing to a predetermined conversion and adding mono or diolefin thereto | |
| US3974094A (en) | Catalyst system for the production of polyalkenamers | |
| US3367924A (en) | Polymerization of bicyclo[2.2.1]-hept-2-ene compounds in aqueous emulsion | |
| US4239874A (en) | Cyclopentene copolymerization process | |
| EP0002279B1 (en) | Process for preparing polymers of cyclopentadiene and bicycloheptene mixtures | |
| US3464965A (en) | Process for producing polybutadienes having reduced cold flow tendency | |
| US3836593A (en) | Polyalkenamers and process for the preparation thereof | |
| US3816382A (en) | Polyalkenamers and process for the preparation thereof | |
| US3366616A (en) | Novel polymeric compositions obtained by the polymerization of 1-phenylcyclobutene or bicyclo(4.2.0)oct-7-ene | |
| US3816384A (en) | Polyalkenamers and process for the preparation thereof | |
| DE2106302B2 (de) | Verfahren zur Polymerisation von alicyclischen Verbindungen | |
| CA1103845A (en) | Process for the preparation of copolymers of cyclopentene with unsaturated alicyclic compounds | |
| CA1106542A (en) | Process for the polymerization of cycloolefins | |
| US3849509A (en) | Polyalkenamers and process for the preparation thereof | |
| DE3751186T2 (de) | Verfahren zur Herstellung von modifizierten Polycycloolefinen. | |
| DE1920500A1 (de) | Katalysator fuer die ringoeffnende Polymerisation von Cyclopenten | |
| Bell | Polymerization of conjugated trienes |