CA2284237C - Catalyse de cycloalcenes en oligomeres polycyclique satures - Google Patents

Catalyse de cycloalcenes en oligomeres polycyclique satures Download PDF

Info

Publication number: CA2284237C
Authority: CA; Canada
Prior art keywords: component; catalyst system; polymerization; group; molar ratio
Prior art date: 1994-01-31
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 - Fee Related

Application number

CA002284237A

Other languages

English (en)

Other versions

CA2284237A1 (fr

Inventor

Jacques Leonard

Claude Guay

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.)

Universite Laval

Original Assignee

Universite Laval

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.)

1994-01-31

Filing date

1994-01-31

Publication date

2002-03-26

1994-01-31 Application filed by Universite Laval filed Critical Universite Laval

1994-01-31 Priority claimed from CA002180725A external-priority patent/CA2180725C/fr

1995-08-03 Publication of CA2284237A1 publication Critical patent/CA2284237A1/fr

2002-03-26 Application granted granted Critical

2002-03-26 Publication of CA2284237C publication Critical patent/CA2284237C/fr

2014-01-31 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

150000001925 cycloalkenes Chemical class 0.000 title claims abstract description 14
125000003367 polycyclic group Chemical group 0.000 title claims abstract description 10
238000006555 catalytic reaction Methods 0.000 title abstract description 3
239000003054 catalyst Substances 0.000 claims abstract description 43
150000003961 organosilicon compounds Chemical class 0.000 claims abstract description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 9
229910052723 transition metal Inorganic materials 0.000 claims abstract description 9
230000000737 periodic effect Effects 0.000 claims abstract description 8
150000003839 salts Chemical class 0.000 claims abstract description 6
150000003624 transition metals Chemical class 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 claims description 32
238000006116 polymerization reaction Methods 0.000 claims description 27
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims description 11
238000000034 method Methods 0.000 claims description 11
229940073561 hexamethyldisiloxane Drugs 0.000 claims description 10
KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 0.000 claims description 10
-1 molybdenum halide Chemical class 0.000 claims description 7
GJWAPAVRQYYSTK-UHFFFAOYSA-N [(dimethyl-$l^{3}-silanyl)amino]-dimethylsilicon Chemical compound C[Si](C)N[Si](C)C GJWAPAVRQYYSTK-UHFFFAOYSA-N 0.000 claims description 5
HTDJPCNNEPUOOQ-UHFFFAOYSA-N hexamethylcyclotrisiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O1 HTDJPCNNEPUOOQ-UHFFFAOYSA-N 0.000 claims description 5
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 5
229910052721 tungsten Inorganic materials 0.000 claims description 5
239000010937 tungsten Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 4
KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 claims description 3
HIMXYMYMHUAZLW-UHFFFAOYSA-N [[[dimethyl(phenyl)silyl]amino]-dimethylsilyl]benzene Chemical compound C=1C=CC=CC=1[Si](C)(C)N[Si](C)(C)C1=CC=CC=C1 HIMXYMYMHUAZLW-UHFFFAOYSA-N 0.000 claims description 3
239000002815 homogeneous catalyst Substances 0.000 claims description 3
229910052750 molybdenum Inorganic materials 0.000 claims description 3
239000011733 molybdenum Substances 0.000 claims description 3
125000005375 organosiloxane group Chemical group 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 description 19
VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 description 14
229910009201 Sn(CH3)4 Inorganic materials 0.000 description 12
URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 10
239000004913 cyclooctene Substances 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
229920000642 polymer Polymers 0.000 description 9
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
238000012662 bulk polymerization Methods 0.000 description 8
239000000203 mixture Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
229910003091 WCl6 Inorganic materials 0.000 description 6
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 6
239000000178 monomer Substances 0.000 description 6
238000007151 ring opening polymerisation reaction Methods 0.000 description 6
239000003708 ampul Substances 0.000 description 5
150000002902 organometallic compounds Chemical class 0.000 description 5
229910052786 argon Inorganic materials 0.000 description 4
NEXSMEBSBIABKL-UHFFFAOYSA-N hexamethyldisilane Chemical compound C[Si](C)(C)[Si](C)(C)C NEXSMEBSBIABKL-UHFFFAOYSA-N 0.000 description 4
ZSMNRKGGHXLZEC-UHFFFAOYSA-N n,n-bis(trimethylsilyl)methanamine Chemical compound C[Si](C)(C)N(C)[Si](C)(C)C ZSMNRKGGHXLZEC-UHFFFAOYSA-N 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
230000003213 activating effect Effects 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
230000000694 effects Effects 0.000 description 3
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
229910018557 Si O Inorganic materials 0.000 description 2
230000002411 adverse Effects 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 2
NMVXHZSPDTXJSJ-UHFFFAOYSA-L 2-methylpropylaluminum(2+);dichloride Chemical compound CC(C)C[Al](Cl)Cl NMVXHZSPDTXJSJ-UHFFFAOYSA-L 0.000 description 1
CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
WSWMGHRLUYADNA-UHFFFAOYSA-N 7-nitro-1,2,3,4-tetrahydroquinoline Chemical compound C1CCNC2=CC([N+](=O)[O-])=CC=C21 WSWMGHRLUYADNA-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
YOUIDGQAIILFBW-UHFFFAOYSA-J Tungsten(IV) chloride Inorganic materials Cl[W](Cl)(Cl)Cl YOUIDGQAIILFBW-UHFFFAOYSA-J 0.000 description 1
125000005234 alkyl aluminium group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
125000002091 cationic group Chemical group 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
LSALTGRCOGBBFR-UHFFFAOYSA-L dibromotungsten Chemical compound Br[W]Br LSALTGRCOGBBFR-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
JJSGABFIILQOEY-UHFFFAOYSA-M diethylalumanylium;bromide Chemical compound CC[Al](Br)CC JJSGABFIILQOEY-UHFFFAOYSA-M 0.000 description 1
HRXSKIOIHQEGAI-UHFFFAOYSA-M diethylalumanylium;fluoride Chemical compound CC[Al](F)CC HRXSKIOIHQEGAI-UHFFFAOYSA-M 0.000 description 1
PPQUYYAZSOKTQD-UHFFFAOYSA-M diethylalumanylium;iodide Chemical compound CC[Al](I)CC PPQUYYAZSOKTQD-UHFFFAOYSA-M 0.000 description 1
YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
BMKSRUJKNOBSHP-UHFFFAOYSA-L diiodotungsten Chemical compound I[W]I BMKSRUJKNOBSHP-UHFFFAOYSA-L 0.000 description 1
239000000539 dimer Substances 0.000 description 1
ZMXPNWBFRPIZFV-UHFFFAOYSA-M dipropylalumanylium;chloride Chemical compound [Cl-].CCC[Al+]CCC ZMXPNWBFRPIZFV-UHFFFAOYSA-M 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
MGDOJPNDRJNJBK-UHFFFAOYSA-N ethylaluminum Chemical compound [Al].C[CH2] MGDOJPNDRJNJBK-UHFFFAOYSA-N 0.000 description 1
JFICPAADTOQAMU-UHFFFAOYSA-L ethylaluminum(2+);dibromide Chemical compound CC[Al](Br)Br JFICPAADTOQAMU-UHFFFAOYSA-L 0.000 description 1
UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
238000005227 gel permeation chromatography Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
OQVJXQJWYQNWTI-UHFFFAOYSA-H hexabromotungsten Chemical compound Br[W](Br)(Br)(Br)(Br)Br OQVJXQJWYQNWTI-UHFFFAOYSA-H 0.000 description 1
239000003446 ligand Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000002751 molybdenum Chemical class 0.000 description 1
GICWIDZXWJGTCI-UHFFFAOYSA-I molybdenum pentachloride Chemical compound Cl[Mo](Cl)(Cl)(Cl)Cl GICWIDZXWJGTCI-UHFFFAOYSA-I 0.000 description 1
OYMJNIHGVDEDFX-UHFFFAOYSA-J molybdenum tetrachloride Chemical compound Cl[Mo](Cl)(Cl)Cl OYMJNIHGVDEDFX-UHFFFAOYSA-J 0.000 description 1
ZSSVQAGPXAAOPV-UHFFFAOYSA-K molybdenum trichloride Chemical compound Cl[Mo](Cl)Cl ZSSVQAGPXAAOPV-UHFFFAOYSA-K 0.000 description 1
GMMJTCLAKDKBCZ-UHFFFAOYSA-L molybdenum(ii) bromide Chemical compound Br[Mo]Br GMMJTCLAKDKBCZ-UHFFFAOYSA-L 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
BGRYSGVIVVUJHH-UHFFFAOYSA-N prop-2-ynyl propanoate Chemical compound CCC(=O)OCC#C BGRYSGVIVVUJHH-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
239000005060 rubber Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
229920003051 synthetic elastomer Polymers 0.000 description 1
239000005061 synthetic rubber Substances 0.000 description 1
NJASUIDIZMMYED-UHFFFAOYSA-N tetra(propan-2-yl)stannane Chemical compound CC(C)[Sn](C(C)C)(C(C)C)C(C)C NJASUIDIZMMYED-UHFFFAOYSA-N 0.000 description 1
WWJBJTBTXOHQAZ-UHFFFAOYSA-J tetrabromomolybdenum Chemical compound Br[Mo](Br)(Br)Br WWJBJTBTXOHQAZ-UHFFFAOYSA-J 0.000 description 1
AFCAKJKUYFLYFK-UHFFFAOYSA-N tetrabutyltin Chemical compound CCCC[Sn](CCCC)(CCCC)CCCC AFCAKJKUYFLYFK-UHFFFAOYSA-N 0.000 description 1
DNVMCVHRVFLVJM-UHFFFAOYSA-N tetrahexylstannane Chemical compound CCCCCC[Sn](CCCCCC)(CCCCCC)CCCCCC DNVMCVHRVFLVJM-UHFFFAOYSA-N 0.000 description 1
MMCXETIAXNXKPE-UHFFFAOYSA-J tetraiodotungsten Chemical compound I[W](I)(I)I MMCXETIAXNXKPE-UHFFFAOYSA-J 0.000 description 1
CKPJWJGGZOJURQ-UHFFFAOYSA-N tetrakis(2-methylpropyl)stannane Chemical compound CC(C)C[Sn](CC(C)C)(CC(C)C)CC(C)C CKPJWJGGZOJURQ-UHFFFAOYSA-N 0.000 description 1
JTGNPNLBCGBCMP-UHFFFAOYSA-N tetraoctylstannane Chemical compound CCCCCCCC[Sn](CCCCCCCC)(CCCCCCCC)CCCCCCCC JTGNPNLBCGBCMP-UHFFFAOYSA-N 0.000 description 1
OIQCWAIEHVRCCG-UHFFFAOYSA-N tetrapropylstannane Chemical compound CCC[Sn](CCC)(CCC)CCC OIQCWAIEHVRCCG-UHFFFAOYSA-N 0.000 description 1
150000003606 tin compounds Chemical class 0.000 description 1
YPFBRNLUIFQCQL-UHFFFAOYSA-K tribromomolybdenum Chemical compound Br[Mo](Br)Br YPFBRNLUIFQCQL-UHFFFAOYSA-K 0.000 description 1
SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-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
239000013638 trimer Substances 0.000 description 1
JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-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
UXVOMHPBSSIGNQ-UHFFFAOYSA-I tungsten(v) bromide Chemical compound Br[W](Br)(Br)(Br)Br UXVOMHPBSSIGNQ-UHFFFAOYSA-I 0.000 description 1
WIDQNNDDTXUPAN-UHFFFAOYSA-I tungsten(v) chloride Chemical compound Cl[W](Cl)(Cl)(Cl)Cl WIDQNNDDTXUPAN-UHFFFAOYSA-I 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/69—Chromium, molybdenum, tungsten or compounds thereof
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F132/00—Homopolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F132/02—Homopolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings
- C08F132/04—Homopolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings having one carbon-to-carbon double bond
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F132/00—Homopolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F132/08—Homopolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having condensed rings
- 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

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Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)

CA002284237A 1994-01-31 1994-01-31 Catalyse de cycloalcenes en oligomeres polycyclique satures Expired - Fee Related CA2284237C (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA002180725A CA2180725C (fr)	1994-01-31	1994-01-31	Polymerisation de cycloalcenes

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002180725A Division CA2180725C (fr)	1994-01-31	1994-01-31	Polymerisation de cycloalcenes

Publications (2)

Publication Number	Publication Date
CA2284237A1 CA2284237A1 (fr)	1995-08-03
CA2284237C true CA2284237C (fr)	2002-03-26

Family

ID=4158564

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002284237A Expired - Fee Related CA2284237C (fr)	1994-01-31	1994-01-31	Catalyse de cycloalcenes en oligomeres polycyclique satures

Country Status (1)

Country	Link
CA (1)	CA2284237C (fr)

1994
- 1994-01-31 CA CA002284237A patent/CA2284237C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2284237A1 (fr)	1995-08-03

Legal Events

Date	Code	Title	Description
1999-10-01	EEER	Examination request
2007-01-31	MKLA	Lapsed

Publication	Publication Date	Title
US4380617A (en)	1983-04-19	Preparation of polymers from cycloolefins
US5194534A (en)	1993-03-16	Tungsten-imido catalysts for ring-opening metathesis polymerization of cycloolefins
EP0424833A2 (fr)	1991-05-02	Fibres d'reenforcement couverts avec catalysateur d'methathesis
US4020254A (en)	1977-04-26	Metathesis polymerization of cycloolefins
US3935179A (en)	1976-01-27	Cycloolefin metathesis
US5155188A (en)	1992-10-13	Oxide cocatalysts in ring opening polymerization of polycycloolefins
US4981931A (en)	1991-01-01	Discrete tungsten complexes as oxygen and water resistant DCPD polymerization catalysts
US5459213A (en)	1995-10-17	Catalyst system for olefin polymerization
US3597406A (en)	1971-08-03	Polymers of hydrocarbon substituted 1,5-cyclooctadienes and methods for their polymerization
CA2284237C (fr)	2002-03-26	Catalyse de cycloalcenes en oligomeres polycyclique satures
CA2180725C (fr)	2000-06-13	Polymerisation de cycloalcenes
US5278305A (en)	1994-01-11	Catalysts for ring-opening, metathesis polymerization of cyclic olefins
JPH02215827A (ja)	1990-08-28	重合体成形物を製造する方法
JP2520671B2 (ja)	1996-07-31	シクロオレフィン重合体成型品の製法
JPH02191625A (ja)	1990-07-27	ジシクロペンタジエン重合のためのゆつくりしたゲル化／硬化系
EP0324979B1 (fr)	1994-03-23	Mélange de norbornène à durée d'emploi prolongée
US3997471A (en)	1976-12-14	Cycloolefin metathesis catalyst
US4923939A (en)	1990-05-08	Ring opening polymerization with organophosphonium and organoarsonium metathesis catalysts
JP3207857B2 (ja)	2001-09-10	重合方法及び触媒
EP0435146A2 (fr)	1991-07-03	Catalyseur de métathèse à base de pyridinium pour polymériser de cyclooléfines
US5120806A (en)	1992-06-09	Mixed activators for stabilized metathesis catalysts
JPH02185521A (ja)	1990-07-19	成形物の製造方法およびそのための重合用原料組成物
US5075272A (en)	1991-12-24	Mixed activators for stabilized metathesis catalysts
JPH05178970A (ja)	1993-07-20	ジシクロペンタジエン重合体の加熱撓み温度及びガラス転移温度を高める塩素化重合体の使用
Guay et al.	1995	Siloxanes and silazanes as activators for metathesis polymerizations