JPS6111245B2 - - Google Patents

Info

Publication number: JPS6111245B2
Authority: JP; Japan
Prior art keywords: group; polymerization; cyclopentene; catalyst; tungsten
Prior art date: 1977-09-07
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

Application number

JP53109526A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5450598A (en

Inventor

Ei Ofusuteedo Eraato

Daburyuu Donbaa Ken

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Goodyear Tire and Rubber Co

Original Assignee

Goodyear Tire and Rubber Co

Priority date (The priority date 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 date listed.)

1977-09-07

Filing date

1978-09-06

Publication date

1986-04-02

1977-09-07 Priority claimed from US05/831,201 external-priority patent/US4137390A/en

1977-09-07 Priority claimed from US05/831,200 external-priority patent/US4172932A/en

1978-09-06 Application filed by Goodyear Tire and Rubber Co filed Critical Goodyear Tire and Rubber Co

1979-04-20 Publication of JPS5450598A publication Critical patent/JPS5450598A/ja

1986-04-02 Publication of JPS6111245B2 publication Critical patent/JPS6111245B2/ja

Status Granted legal-status Critical Current

Links

239000003054 catalyst Substances 0.000 claims description 43
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 39
238000000034 method Methods 0.000 claims description 38
238000006116 polymerization reaction Methods 0.000 claims description 36
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 24
239000000178 monomer Substances 0.000 claims description 17
239000002904 solvent Substances 0.000 claims description 17
IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 claims description 14
125000001931 aliphatic group Chemical group 0.000 claims description 13
-1 transition metal salt Chemical class 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 10
229910052721 tungsten Inorganic materials 0.000 claims description 10
239000010937 tungsten Substances 0.000 claims description 10
229920000642 polymer Polymers 0.000 claims description 9
150000001875 compounds Chemical class 0.000 claims description 8
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
150000002989 phenols Chemical class 0.000 claims description 7
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 7
229910052723 transition metal Inorganic materials 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 4
229920001577 copolymer Polymers 0.000 claims description 3
229930195733 hydrocarbon Natural products 0.000 claims description 3
SVHOVVJFOWGYJO-UHFFFAOYSA-N pentabromophenol Chemical compound OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br SVHOVVJFOWGYJO-UHFFFAOYSA-N 0.000 claims description 3
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
150000001334 alicyclic compounds Chemical class 0.000 claims 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
239000007809 chemical reaction catalyst Substances 0.000 claims 1
229920006395 saturated elastomer Polymers 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
150000001336 alkenes Chemical class 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
235000019441 ethanol Nutrition 0.000 description 8
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 8
238000007151 ring opening polymerisation reaction Methods 0.000 description 8
UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
230000032683 aging Effects 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
238000011065 in-situ storage Methods 0.000 description 5
230000008569 process Effects 0.000 description 5
239000000047 product Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
150000001925 cycloalkenes Chemical class 0.000 description 4
150000002440 hydroxy compounds Chemical class 0.000 description 4
239000002685 polymerization catalyst Substances 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
125000003158 alcohol group Chemical group 0.000 description 3
125000002723 alicyclic group Chemical group 0.000 description 3
238000005865 alkene metathesis reaction Methods 0.000 description 3
239000003849 aromatic solvent Substances 0.000 description 3
239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000000463 material Substances 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
150000003624 transition metals Chemical class 0.000 description 3
KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 0.000 description 3
BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 2
LINPIYWFGCPVIE-UHFFFAOYSA-N 2,4,6-trichlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1Cl LINPIYWFGCPVIE-UHFFFAOYSA-N 0.000 description 2
SSIZLKDLDKIHEV-UHFFFAOYSA-N 2,6-dibromophenol Chemical compound OC1=C(Br)C=CC=C1Br SSIZLKDLDKIHEV-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000007334 copolymerization reaction Methods 0.000 description 2
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
150000001993 dienes Chemical class 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
230000006872 improvement Effects 0.000 description 2
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
229930195734 saturated hydrocarbon Natural products 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
150000003657 tungsten Chemical class 0.000 description 2
YEUZDWLVCVNEAO-UITAMQMPSA-N (1z)-3-phenylcyclooctene Chemical compound C1CCCC\C=C/C1C1=CC=CC=C1 YEUZDWLVCVNEAO-UITAMQMPSA-N 0.000 description 1
HOEFIGOFJSMARD-FUOWLQLWSA-N (1z,5z)-1-methylcycloocta-1,5-diene Chemical compound C\C1=C\CC\C=C/CC1 HOEFIGOFJSMARD-FUOWLQLWSA-N 0.000 description 1
QCSDLMPAQMQZOE-QSWGICILSA-N (1z,9z)-cyclohexadeca-1,9-diene Chemical compound C1CCC\C=C/CCCCCC\C=C/CC1 QCSDLMPAQMQZOE-QSWGICILSA-N 0.000 description 1
XDBUHVQGOZJAHE-UHFFFAOYSA-N 1,2-dimethylcycloocta-1,5-diene Chemical compound CC1=C(C)CCC=CCC1 XDBUHVQGOZJAHE-UHFFFAOYSA-N 0.000 description 1
VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
239000004912 1,5-cyclooctadiene Substances 0.000 description 1
PHQVPLFRGMMSCP-UHFFFAOYSA-N 1-chlorocycloocta-1,5-diene Chemical compound ClC1=CCCC=CCC1 PHQVPLFRGMMSCP-UHFFFAOYSA-N 0.000 description 1
RULKYXXCCZZKDZ-UHFFFAOYSA-N 2,3,4,5-tetrachlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C(Cl)=C1Cl RULKYXXCCZZKDZ-UHFFFAOYSA-N 0.000 description 1
VGVRPFIJEJYOFN-UHFFFAOYSA-N 2,3,4,6-tetrachlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1Cl VGVRPFIJEJYOFN-UHFFFAOYSA-N 0.000 description 1
XGCHAIDDPMFRLJ-UHFFFAOYSA-N 2,3,6-trichlorophenol Chemical compound OC1=C(Cl)C=CC(Cl)=C1Cl XGCHAIDDPMFRLJ-UHFFFAOYSA-N 0.000 description 1
STCITVXZHAUCDV-UHFFFAOYSA-N 2,6-dibromo-3-butylphenol Chemical compound CCCCC1=CC=C(Br)C(O)=C1Br STCITVXZHAUCDV-UHFFFAOYSA-N 0.000 description 1
HKKATEWBBPEIKB-UHFFFAOYSA-N 2,6-dichloro-3,4,5-trimethylphenol Chemical compound CC1=C(C)C(Cl)=C(O)C(Cl)=C1C HKKATEWBBPEIKB-UHFFFAOYSA-N 0.000 description 1
YXEOEPYIBGTLML-UHFFFAOYSA-N 2,6-dichloro-4-methylphenol Chemical compound CC1=CC(Cl)=C(O)C(Cl)=C1 YXEOEPYIBGTLML-UHFFFAOYSA-N 0.000 description 1
HOLHYSJJBXSLMV-UHFFFAOYSA-N 2,6-dichlorophenol Chemical compound OC1=C(Cl)C=CC=C1Cl HOLHYSJJBXSLMV-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
FCMQLFSNSPWIAZ-UHFFFAOYSA-N 2-bromo-6-chloro-4-ethylphenol Chemical compound CCC1=CC(Cl)=C(O)C(Br)=C1 FCMQLFSNSPWIAZ-UHFFFAOYSA-N 0.000 description 1
LUECOFFMVWPWDR-UHFFFAOYSA-N 2-bromo-6-chlorophenol Chemical compound OC1=C(Cl)C=CC=C1Br LUECOFFMVWPWDR-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
229940093475 2-ethoxyethanol Drugs 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
WDNBURPWRNALGP-UHFFFAOYSA-N 3,4-Dichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1 WDNBURPWRNALGP-UHFFFAOYSA-N 0.000 description 1
SCWBSTVOWDDYHH-UHFFFAOYSA-N 4-amino-2,6-dichlorophenol;4-aminophenol Chemical compound NC1=CC=C(O)C=C1.NC1=CC(Cl)=C(O)C(Cl)=C1 SCWBSTVOWDDYHH-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004129 EU approved improving agent Substances 0.000 description 1
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
QRSFFHRCBYCWBS-UHFFFAOYSA-N [O].[O] Chemical compound [O].[O] QRSFFHRCBYCWBS-UHFFFAOYSA-N 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000007824 aliphatic compounds Chemical class 0.000 description 1
125000001118 alkylidene group Chemical group 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
HQMRIBYCTLBDAK-UHFFFAOYSA-M bis(2-methylpropyl)alumanylium;chloride Chemical compound CC(C)C[Al](Cl)CC(C)C HQMRIBYCTLBDAK-UHFFFAOYSA-M 0.000 description 1
238000009835 boiling Methods 0.000 description 1
NZIXICKPQWIFAU-UHFFFAOYSA-K bromo(dimethyl)alumane;dibromo(methyl)alumane Chemical compound C[Al](C)Br.C[Al](Br)Br NZIXICKPQWIFAU-UHFFFAOYSA-K 0.000 description 1
JKRAPJXEWBPBTP-UHFFFAOYSA-M bromo(dipropyl)alumane Chemical compound [Br-].CCC[Al+]CCC JKRAPJXEWBPBTP-UHFFFAOYSA-M 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
OCFSGVNHPVWWKD-UHFFFAOYSA-N butylaluminum Chemical compound [Al].[CH2]CCC OCFSGVNHPVWWKD-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
230000008859 change Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000003426 co-catalyst Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
125000004966 cyanoalkyl group Chemical group 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
ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-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
XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
WAUAJTBCLLNWQZ-UHFFFAOYSA-L dibromo(2-methylpropyl)alumane Chemical compound [Br-].[Br-].CC(C)C[Al+2] WAUAJTBCLLNWQZ-UHFFFAOYSA-L 0.000 description 1
RFUDQCRVCDXBGK-UHFFFAOYSA-L dichloro(propyl)alumane Chemical compound [Cl-].[Cl-].CCC[Al+2] RFUDQCRVCDXBGK-UHFFFAOYSA-L 0.000 description 1
HRXSKIOIHQEGAI-UHFFFAOYSA-M diethylalumanylium;fluoride Chemical compound CC[Al](F)CC HRXSKIOIHQEGAI-UHFFFAOYSA-M 0.000 description 1
YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
238000007323 disproportionation reaction Methods 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
150000002085 enols Chemical class 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
239000000835 fiber Substances 0.000 description 1
238000010528 free radical solution polymerization reaction Methods 0.000 description 1
OQVJXQJWYQNWTI-UHFFFAOYSA-H hexabromotungsten Chemical compound Br[W](Br)(Br)(Br)(Br)Br OQVJXQJWYQNWTI-UHFFFAOYSA-H 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000005649 metathesis reaction Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
150000002751 molybdenum Chemical class 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
238000006213 oxygenation reaction Methods 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
229920003246 polypentenamer Polymers 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000005215 recombination Methods 0.000 description 1
230000006798 recombination Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000008521 reorganization Effects 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003623 transition metal compounds Chemical class 0.000 description 1
VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
NXHILIPIEUBEPD-UHFFFAOYSA-H tungsten hexafluoride Chemical compound F[W](F)(F)(F)(F)F NXHILIPIEUBEPD-UHFFFAOYSA-H 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-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)
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)
Polymerization Catalysts (AREA)

JP10952678A 1977-09-07 1978-09-06 Cyclopentene polymer and preparation thereof Granted JPS5450598A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US05/831,201 US4137390A (en)	1977-09-07	1977-09-07	Process for the polymerization of cycloolefins
US05/831,200 US4172932A (en)	1977-09-07	1977-09-07	Process for the preparation of polymers of cyclopentene or copolymers of cyclopentene with unsaturated alicyclic compounds

Publications (2)

Publication Number	Publication Date
JPS5450598A JPS5450598A (en)	1979-04-20
JPS6111245B2 true JPS6111245B2 (de)	1986-04-02

Family

ID=27125420

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP10952678A Granted JPS5450598A (en)	1977-09-07	1978-09-06	Cyclopentene polymer and preparation thereof

Country Status (8)

Country	Link
JP (1)	JPS5450598A (de)
BR (1)	BR7805776A (de)
DE (1)	DE2838303A1 (de)
FR (1)	FR2402670A1 (de)
GB (1)	GB2003894B (de)
IT (1)	IT1106123B (de)
MX (1)	MX152257A (de)
NL (1)	NL7808806A (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS636642U (de) *	1986-06-30	1988-01-18
JPS63116940U (de) *	1987-01-20	1988-07-28

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4260702A (en) *	1979-11-26	1981-04-07	Minnesota Mining And Manufacturing Company	Polymers containing cyclic ether units joined through 2,6-diyl linkages
AU602424B2 (en) *	1987-08-24	1990-10-11	Hercules Incorporated	Strained ring cycloolefin polymer and catalyst and method for making same
US8889786B2 (en)	2010-09-30	2014-11-18	Zeon Corporation	Cyclopentene ring-opening polymer and method of production of same
US10400060B2 (en)	2014-06-19	2019-09-03	Zeon Corporation	Cyclopentene ring-opening polymer and method of production of same, polymer composition, and cross-linked polymer
CN116253971B (zh) *	2023-01-13	2024-05-31	浙江吉利控股集团有限公司	一种轻量化材料、导流罩的制备方法、导流罩组件以及汽车

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1770491C3 (de) *	1968-05-24	1982-07-08	Bayer Ag, 5090 Leverkusen	Verfahren zur Herstellung von trans-Polynentenamer
US3790545A (en) *	1972-05-18	1974-02-05	Goodrich Co B F	Preparation of high cis-content polypentenamer polymers
US4038471A (en) *	1976-10-29	1977-07-26	The Goodyear Tire & Rubber Company	Method for preparing high-cis polyalkenamers

1978
- 1978-08-21 GB GB7834035A patent/GB2003894B/en not_active Expired
- 1978-08-23 MX MX174615A patent/MX152257A/es unknown
- 1978-08-25 NL NL7808806A patent/NL7808806A/xx not_active Application Discontinuation
- 1978-09-01 DE DE19782838303 patent/DE2838303A1/de not_active Withdrawn
- 1978-09-04 FR FR7825399A patent/FR2402670A1/fr active Granted
- 1978-09-05 BR BR7805776A patent/BR7805776A/pt unknown
- 1978-09-06 JP JP10952678A patent/JPS5450598A/ja active Granted
- 1978-09-06 IT IT50994/78A patent/IT1106123B/it active

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS636642U (de) *	1986-06-30	1988-01-18
JPS63116940U (de) *	1987-01-20	1988-07-28

Also Published As

Publication number	Publication date
IT1106123B (it)	1985-11-11
NL7808806A (nl)	1979-03-09
FR2402670B1 (de)	1980-07-04
GB2003894B (en)	1982-03-24
BR7805776A (pt)	1979-04-24
FR2402670A1 (fr)	1979-04-06
DE2838303A1 (de)	1979-03-15
IT7850994A0 (it)	1978-09-06
GB2003894A (en)	1979-03-21
MX152257A (es)	1985-06-14
JPS5450598A (en)	1979-04-20

Publication	Publication Date	Title
US3974092A (en)	1976-08-10	Catalyst for the preparation of polyalkenamers
US3798175A (en)	1974-03-19	Catalysts for the ring opening polymerization of cyclic olefins
US5519101A (en)	1996-05-21	Process for preparation of unsaturated oligomers or polymers by acyclic olefin metathesis
US3935179A (en)	1976-01-27	Cycloolefin metathesis
US3522332A (en)	1970-07-28	Process for the preparation of 1,2-polybutadiene
US4020254A (en)	1977-04-26	Metathesis polymerization of cycloolefins
US4239874A (en)	1980-12-16	Cyclopentene copolymerization process
US3974094A (en)	1976-08-10	Catalyst system for the production of polyalkenamers
US4038471A (en)	1977-07-26	Method for preparing high-cis polyalkenamers
US4172932A (en)	1979-10-30	Process for the preparation of polymers of cyclopentene or copolymers of cyclopentene with unsaturated alicyclic compounds
US5403904A (en)	1995-04-04	Process for preparation of telechelic difunctional unsaturated oligomers or polymers by acyclic olefin metathesis
US4137390A (en)	1979-01-30	Process for the polymerization of cycloolefins
JPS6111245B2 (de)	1986-04-02
US3853830A (en)	1974-12-10	Process for preparing polymers of cyclopentene
KR100203193B1 (ko)	1999-06-15	알파-올레핀의 중합에 이용할 수 있는 혼합촉매 조성물
US5028672A (en)	1991-07-02	Catalyst and process for polymerization of norbornene derivatives
US3228917A (en)	1966-01-11	Method of polymerizing olefins with nickel or cobalt salt-organophosphine complex and an acidic metal halide
US5369195A (en)	1994-11-29	Polymerization of cyclic olefins
CA1042594A (en)	1978-11-14	Metathesis of cycloolefins
CA1134550A (en)	1982-10-26	Cyclopentene copolymerization process
US3691144A (en)	1972-09-12	Olefin polymerization using complexes of mo and w, containing no with organoaluminums
US3849509A (en)	1974-11-19	Polyalkenamers and process for the preparation thereof
US3538171A (en)	1970-11-03	Process for the isomerization of 5-vinylbicyclo(2.2.1)hept-2-ene
EP0677074B1 (de)	1997-04-16	Kupferhydride als co-katalysatoren für die polymerisation von cycloolefinen
US3997471A (en)	1976-12-14	Cycloolefin metathesis catalyst

JPS6111245B2 - - Google Patents

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ID=27125420

Family Applications (1)

Country Status (8)

Cited By (2)

Families Citing this family (5)

Family Cites Families (3)

Cited By (2)

Also Published As

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