CA2005688A1 - Cocataslyseurs a base d'oxyde pour la polymerisation de poly(olefines cycliques) avec ouverture de cycle - Google Patents

Cocataslyseurs a base d'oxyde pour la polymerisation de poly(olefines cycliques) avec ouverture de cycle

Info

Publication number: CA2005688A1
Authority: CA; Canada
Prior art keywords: carbon atoms; catalyst; cocatalyst; monomer; radicals
Prior art date: 1988-12-29
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.): Abandoned

Application number

CA 2005688

Other languages

English (en)

Inventor

Brian L. Goodall

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.)

Goodrich Corp

Original Assignee

BF Goodrich Corp

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.)

1988-12-29

Filing date

1989-12-15

Publication date

1990-06-29

1989-12-15 Application filed by BF Goodrich Corp filed Critical BF Goodrich Corp

1990-06-29 Publication of CA2005688A1 publication Critical patent/CA2005688A1/fr

Status Abandoned legal-status Critical Current

Links

238000007151 ring opening polymerisation reaction Methods 0.000 title claims abstract description 5
229920003050 poly-cycloolefin Polymers 0.000 title description 2
239000003054 catalyst Substances 0.000 claims abstract description 55
150000001925 cycloalkenes Chemical class 0.000 claims abstract description 25
238000005649 metathesis reaction Methods 0.000 claims abstract description 18
239000000203 mixture Substances 0.000 claims abstract description 13
125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 claims abstract description 9
239000000178 monomer Substances 0.000 claims description 65
125000004432 carbon atom Chemical group C* 0.000 claims description 37
238000000034 method Methods 0.000 claims description 26
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 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 20
238000006116 polymerization reaction Methods 0.000 claims description 20
239000002904 solvent Substances 0.000 claims description 19
OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 14
229910052721 tungsten Inorganic materials 0.000 claims description 14
239000010937 tungsten Substances 0.000 claims description 14
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 9
229910052782 aluminium Chemical group 0.000 claims description 9
150000004820 halides Chemical class 0.000 claims description 9
229910052750 molybdenum Inorganic materials 0.000 claims description 9
239000011733 molybdenum Substances 0.000 claims description 9
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 8
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
229930195733 hydrocarbon Natural products 0.000 claims description 8
150000003658 tungsten compounds Chemical class 0.000 claims description 8
150000002430 hydrocarbons Chemical class 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
239000000460 chlorine Chemical group 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
229910052710 silicon Inorganic materials 0.000 claims description 5
239000010703 silicon Substances 0.000 claims description 5
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000004122 cyclic group Chemical group 0.000 claims description 4
229910052732 germanium Inorganic materials 0.000 claims description 4
GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 4
229920000642 polymer Polymers 0.000 claims description 4
229910052718 tin Inorganic materials 0.000 claims description 4
239000013638 trimer Substances 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
230000000379 polymerizing effect Effects 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
INYHZQLKOKTDAI-UHFFFAOYSA-N 5-ethenylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=C)CC1C=C2 INYHZQLKOKTDAI-UHFFFAOYSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
239000005046 Chlorosilane Substances 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
YGHUUVGIRWMJGE-UHFFFAOYSA-N chlorodimethylsilane Chemical group C[SiH](C)Cl YGHUUVGIRWMJGE-UHFFFAOYSA-N 0.000 claims description 2
KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical group Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 claims description 2
OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 claims description 2
LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 claims description 2
150000003482 tantalum compounds Chemical class 0.000 claims description 2
RMDKEBZUCHXUER-UHFFFAOYSA-N 4-methylbicyclo[2.2.1]hept-2-ene Chemical compound C1CC2C=CC1(C)C2 RMDKEBZUCHXUER-UHFFFAOYSA-N 0.000 claims 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
125000001153 fluoro group Chemical group F* 0.000 claims 1
229910052740 iodine Chemical group 0.000 claims 1
239000011630 iodine Chemical group 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000005078 molybdenum compound Substances 0.000 claims 1
150000002752 molybdenum compounds Chemical group 0.000 claims 1
JFNLZVQOOSMTJK-UHFFFAOYSA-N norbornene Chemical class C1C2CCC1C=C2 JFNLZVQOOSMTJK-UHFFFAOYSA-N 0.000 claims 1
XBFJAVXCNXDMBH-UHFFFAOYSA-N tetracyclo[6.2.1.1(3,6).0(2,7)]dodec-4-ene Chemical compound C1C(C23)C=CC1C3C1CC2CC1 XBFJAVXCNXDMBH-UHFFFAOYSA-N 0.000 claims 1
229920001187 thermosetting polymer Polymers 0.000 claims 1
239000000243 solution Substances 0.000 description 34
-1 tungsten halide Chemical class 0.000 description 25
YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 12
229910000086 alane Inorganic materials 0.000 description 11
238000002360 preparation method Methods 0.000 description 9
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 8
125000005234 alkyl aluminium group Chemical group 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000004215 Carbon black (E152) Substances 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 4
239000012190 activator Substances 0.000 description 4
150000001721 carbon Chemical group 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 4
239000011133 lead Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
239000005049 silicon tetrachloride Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
229910020175 SiOH Inorganic materials 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000010528 free radical solution polymerization reaction Methods 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
125000002524 organometallic group Chemical group 0.000 description 3
150000002989 phenols Chemical class 0.000 description 3
VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 3
SBXWFLISHPUINY-UHFFFAOYSA-N triphenyltin Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 SBXWFLISHPUINY-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
239000002879 Lewis base Substances 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
240000001987 Pyrus communis Species 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
229940010552 ammonium molybdate Drugs 0.000 description 2
235000018660 ammonium molybdate Nutrition 0.000 description 2
239000011609 ammonium molybdate Substances 0.000 description 2
238000012662 bulk polymerization Methods 0.000 description 2
239000013522 chelant Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 2
239000004914 cyclooctane Substances 0.000 description 2
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
150000007527 lewis bases Chemical class 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000003607 modifier Substances 0.000 description 2
MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 2
GDSGXRQXKTWBOS-UHFFFAOYSA-N n,n-di(tridecyl)tridecan-1-amine Chemical compound CCCCCCCCCCCCCN(CCCCCCCCCCCCC)CCCCCCCCCCCCC GDSGXRQXKTWBOS-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
150000002848 norbornenes Chemical class 0.000 description 2
QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
238000010107 reaction injection moulding Methods 0.000 description 2
239000011135 tin Substances 0.000 description 2
WVMSIBFANXCZKT-UHFFFAOYSA-N triethyl(hydroxy)silane Chemical compound CC[Si](O)(CC)CC WVMSIBFANXCZKT-UHFFFAOYSA-N 0.000 description 2
RZUNIXAGSKNOIB-HSFFGMMNSA-N (1z,3e)-cyclododeca-1,3-diene Chemical compound C1CCCC\C=C/C=C/CCC1 RZUNIXAGSKNOIB-HSFFGMMNSA-N 0.000 description 1
LGAQJENWWYGFSN-PLNGDYQASA-N (z)-4-methylpent-2-ene Chemical compound C\C=C/C(C)C LGAQJENWWYGFSN-PLNGDYQASA-N 0.000 description 1
NJECQESCCSENHG-UHFFFAOYSA-N 1,1,2,2,3,3,4,4-octamethyltetrasiletane Chemical compound C[Si]1(C)[Si](C)(C)[Si](C)(C)[Si]1(C)C NJECQESCCSENHG-UHFFFAOYSA-N 0.000 description 1
IFDLXKQSUOWIBO-UHFFFAOYSA-N 1,3-dichloropropan-1-ol Chemical compound OC(Cl)CCCl IFDLXKQSUOWIBO-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-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
QIJNJJZPYXGIQM-UHFFFAOYSA-N 1lambda4,2lambda4-dimolybdacyclopropa-1,2,3-triene Chemical compound [Mo]=C=[Mo] QIJNJJZPYXGIQM-UHFFFAOYSA-N 0.000 description 1
LAZHUUGOLCHESB-UHFFFAOYSA-N 2,3-dimethylbicyclo[2.2.1]hept-5-ene Chemical compound C1C2C(C)C(C)C1C=C2 LAZHUUGOLCHESB-UHFFFAOYSA-N 0.000 description 1
SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
YSWATWCBYRBYBO-UHFFFAOYSA-N 5-butylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCC)CC1C=C2 YSWATWCBYRBYBO-UHFFFAOYSA-N 0.000 description 1
VVKPRHOUENDOED-UHFFFAOYSA-N 5-dodecylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCCCCCCCC)CC1C=C2 VVKPRHOUENDOED-UHFFFAOYSA-N 0.000 description 1
QHJIJNGGGLNBNJ-UHFFFAOYSA-N 5-ethylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CC)CC1C=C2 QHJIJNGGGLNBNJ-UHFFFAOYSA-N 0.000 description 1
PCBPVYHMZBWMAZ-UHFFFAOYSA-N 5-methylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C)CC1C=C2 PCBPVYHMZBWMAZ-UHFFFAOYSA-N 0.000 description 1
GOLQZWYZZWIBCA-UHFFFAOYSA-N 5-octylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCCCC)CC1C=C2 GOLQZWYZZWIBCA-UHFFFAOYSA-N 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
101100234002 Drosophila melanogaster Shal gene Proteins 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
101150046160 POL1 gene Proteins 0.000 description 1
244000166071 Shorea robusta Species 0.000 description 1
235000015076 Shorea robusta Nutrition 0.000 description 1
101100117436 Thermus aquaticus polA gene Proteins 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000000654 additive Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-UHFFFAOYSA-N 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
ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
230000009849 deactivation Effects 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
CQYBWJYIKCZXCN-UHFFFAOYSA-N diethylaluminum Chemical group CC[Al]CC CQYBWJYIKCZXCN-UHFFFAOYSA-N 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000005538 encapsulation Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
PHTXVQQRWJXYPP-UHFFFAOYSA-N ethyltrifluoromethylaminoindane Chemical compound C1=C(C(F)(F)F)C=C2CC(NCC)CC2=C1 PHTXVQQRWJXYPP-UHFFFAOYSA-N 0.000 description 1
BFWMWWXRWVJXSE-UHFFFAOYSA-M fentin hydroxide Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(O)C1=CC=CC=C1 BFWMWWXRWVJXSE-UHFFFAOYSA-M 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 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
239000011414 polymer cement Substances 0.000 description 1
230000002028 premature Effects 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
239000011343 solid material Substances 0.000 description 1
230000007928 solubilization Effects 0.000 description 1
238000005063 solubilization Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
AFCAKJKUYFLYFK-UHFFFAOYSA-N tetrabutyltin Chemical compound CCCC[Sn](CCCC)(CCCC)CCCC AFCAKJKUYFLYFK-UHFFFAOYSA-N 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
230000008719 thickening Effects 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Landscapes

Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)

CA 2005688 1988-12-29 1989-12-15 Cocataslyseurs a base d'oxyde pour la polymerisation de poly(olefines cycliques) avec ouverture de cycle Abandoned CA2005688A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US29034588A	1988-12-29	1988-12-29
US07/290,345		1988-12-29

Publications (1)

Publication Number	Publication Date
CA2005688A1 true CA2005688A1 (fr)	1990-06-29

Family

ID=23115566

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2005688 Abandoned CA2005688A1 (fr)	1988-12-29	1989-12-15	Cocataslyseurs a base d'oxyde pour la polymerisation de poly(olefines cycliques) avec ouverture de cycle

Country Status (2)

Country	Link
JP (1)	JP2826754B2 (fr)
CA (1)	CA2005688A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR101573707B1 (ko)	2014-02-06	2015-12-02	경상대학교 산학협력단	ｐ―ＤＣＰＤ 성형품의 고속 압축 성형 방법

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2241569B1 (fr)	1973-08-21	1979-03-02	Ethylene Plastique Sa
US4380617A (en)	1982-01-20	1983-04-19	The B. F. Goodrich Company	Preparation of polymers from cycloolefins
DE3835044A1 (de)	1988-10-14	1990-04-19	Hoechst Ag	Verfahren zur herstellung von cycloolefinpolymeren

1989
- 1989-12-15 CA CA 2005688 patent/CA2005688A1/fr not_active Abandoned
1990
- 1990-01-04 JP JP3390A patent/JP2826754B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
JPH02283721A (ja)	1990-11-21
JP2826754B2 (ja)	1998-11-18

Legal Events

Date	Code	Title	Description
1996-06-16	FZDE	Dead

Publication	Publication Date	Title
CA1222597A (fr)	1987-06-02	Preparation de polymeres a partir d'olefines cycliques
US4899005A (en)	1990-02-06	Method for preparing cycloolefin copolymers with improved heat stability
CA1338482C (fr)	1996-07-23	Composantes, stables au stoackage, de formulations reactives pour polymerisation en masse de monomeres cycloolefiniques
CA1282545C (fr)	1991-04-02	Polycyclo-olefines resistant aux solvants
US5155188A (en)	1992-10-13	Oxide cocatalysts in ring opening polymerization of polycycloolefins
US4923936A (en)	1990-05-08	Heteropolymetallate metathesis catalysts for cycloolefin polymerization
EP0281086B1 (fr)	1994-04-20	Alliages de polymères polycyclo-oléfine utilisant des polymères fonctionnels dispersés à base d'éthylène
US5143992A (en)	1992-09-01	Methathesis polymerizable adducts of a divinylcyclohydrocarbon and cyclopentadiene
CA1330377C (fr)	1994-06-21	Polycycloolefines modifiees
US5066740A (en)	1991-11-19	Pyridinium metathesis catalysts for cycloolefin polymerization
US4923939A (en)	1990-05-08	Ring opening polymerization with organophosphonium and organoarsonium metathesis catalysts
US3997471A (en)	1976-12-14	Cycloolefin metathesis catalyst
JP2826754B2 (ja)	1998-11-18	シクロオレフィンの開環重合法およびそれに用いる触媒
CA1326734C (fr)	1994-02-01	Polymerisation avec un cocatalyseur ouvrant les anneaux
EP0226954A2 (fr)	1987-07-01	Polymérisation de cyclooléfines avec cocatalyseurs non halogénés
CA2152930A1 (fr)	1994-07-21	Hydrures de cuivre, co-catalyseurs de polymerisation
CA2284237C (fr)	2002-03-26	Catalyse de cycloalcenes en oligomeres polycyclique satures
NO175595B (no)	1994-07-25	Fremgangsmåte for fremstilling av en polymer ved ringåpningspolymerisering