CA1108797A - Copolymeres a structure desordonnee de dicyclopentadienes et de composes monocycliques insatures - Google Patents

Copolymeres a structure desordonnee de dicyclopentadienes et de composes monocycliques insatures

Info

Publication number: CA1108797A
Authority: CA; Canada
Prior art keywords: dicyclopentadiene; alkyl; general formula; radical; random copolymers
Prior art date: 1977-09-16
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

CA308,454A

Other languages

English (en)

Inventor

Anthony J. Bell

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.)

1977-09-16

Filing date

1978-07-31

Publication date

1981-09-08

1978-07-31 Application filed by Goodyear Tire and Rubber Co filed Critical Goodyear Tire and Rubber Co

1981-09-08 Application granted granted Critical

1981-09-08 Publication of CA1108797A publication Critical patent/CA1108797A/fr

Status Expired legal-status Critical Current

Links

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 title claims abstract description 31
229920005604 random copolymer Polymers 0.000 title claims abstract description 10
125000002950 monocyclic group Chemical group 0.000 title claims abstract description 6
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims abstract description 19
-1 aralkyl radicals Chemical class 0.000 claims abstract description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 14
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims abstract description 12
239000003054 catalyst Substances 0.000 claims abstract description 11
239000004912 1,5-cyclooctadiene Substances 0.000 claims abstract description 9
239000000203 mixture Substances 0.000 claims abstract description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
238000000034 method Methods 0.000 claims abstract description 8
VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims abstract description 7
150000003961 organosilicon compounds Chemical class 0.000 claims abstract description 6
ZOLLIQAKMYWTBR-RYMQXAEESA-N cyclododecatriene Chemical compound C/1C\C=C\CC\C=C/CC\C=C\1 ZOLLIQAKMYWTBR-RYMQXAEESA-N 0.000 claims abstract description 4
URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 claims abstract description 4
239000004913 cyclooctene Substances 0.000 claims abstract description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims abstract description 3
125000003118 aryl group Chemical group 0.000 claims abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
125000001424 substituent group Chemical group 0.000 claims abstract description 3
229920002554 vinyl polymer Polymers 0.000 claims abstract description 3
ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 claims abstract description 3
KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 0.000 claims abstract 3
150000001923 cyclic compounds Chemical class 0.000 claims abstract 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 6
OLLFKUHHDPMQFR-UHFFFAOYSA-N dihydroxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](O)(O)C1=CC=CC=C1 OLLFKUHHDPMQFR-UHFFFAOYSA-N 0.000 claims description 3
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 3
230000000379 polymerizing effect Effects 0.000 claims description 2
AFCAKJKUYFLYFK-UHFFFAOYSA-N tetrabutyltin Chemical compound CCCC[Sn](CCCC)(CCCC)CCCC AFCAKJKUYFLYFK-UHFFFAOYSA-N 0.000 claims description 2
RWWNQEOPUOCKGR-UHFFFAOYSA-N tetraethyltin Chemical compound CC[Sn](CC)(CC)CC RWWNQEOPUOCKGR-UHFFFAOYSA-N 0.000 claims description 2
VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 claims description 2
229910003091 WCl6 Inorganic materials 0.000 claims 1
JRMHUZLFQVKRNB-UHFFFAOYSA-N bis(ethenyl)-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C=C)(C=C)C1=CC=CC=C1 JRMHUZLFQVKRNB-UHFFFAOYSA-N 0.000 claims 1
238000010528 free radical solution polymerization reaction Methods 0.000 claims 1
NLSXASIDNWDYMI-UHFFFAOYSA-N triphenylsilanol Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(O)C1=CC=CC=C1 NLSXASIDNWDYMI-UHFFFAOYSA-N 0.000 claims 1
238000006116 polymerization reaction Methods 0.000 abstract description 22
238000002360 preparation method Methods 0.000 abstract description 6
239000000243 solution Substances 0.000 description 29
229920001577 copolymer Polymers 0.000 description 13
239000000306 component Substances 0.000 description 9
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
229920000642 polymer Polymers 0.000 description 7
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
239000000178 monomer Substances 0.000 description 6
150000002500 ions Chemical class 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 4
150000001925 cycloalkenes Chemical class 0.000 description 4
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
239000004416 thermosoftening plastic Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZMJBYMUCKBYSCP-UHFFFAOYSA-N Hydroxycitric acid Chemical compound OC(=O)C(O)C(O)(C(O)=O)CC(O)=O ZMJBYMUCKBYSCP-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
150000001993 dienes Chemical class 0.000 description 3
229910001873 dinitrogen Inorganic materials 0.000 description 3
229920001971 elastomer Polymers 0.000 description 3
239000007789 gas Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
238000007151 ring opening polymerisation reaction Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
229920001169 thermoplastic Polymers 0.000 description 3
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000007334 copolymerization reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000806 elastomer Substances 0.000 description 2
230000009477 glass transition Effects 0.000 description 2
230000000977 initiatory effect Effects 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920000136 polysorbate Polymers 0.000 description 2
RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
VYXHVRARDIDEHS-QGTKBVGQSA-N (1z,5z)-cycloocta-1,5-diene Chemical compound C\1C\C=C/CC\C=C/1 VYXHVRARDIDEHS-QGTKBVGQSA-N 0.000 description 1
PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
QWQNFXDYOCUEER-UHFFFAOYSA-N 2,3-ditert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1C(C)(C)C QWQNFXDYOCUEER-UHFFFAOYSA-N 0.000 description 1
101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
102100024133 Coiled-coil domain-containing protein 50 Human genes 0.000 description 1
229920008712 Copo Polymers 0.000 description 1
229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
239000004713 Cyclic olefin copolymer Substances 0.000 description 1
101000910772 Homo sapiens Coiled-coil domain-containing protein 50 Proteins 0.000 description 1
101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
238000005865 alkene metathesis reaction Methods 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000012668 chain scission Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000011010 flushing procedure Methods 0.000 description 1
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000003607 modifier Substances 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
150000003254 radicals Chemical class 0.000 description 1
230000036647 reaction Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
238000012216 screening Methods 0.000 description 1
238000007789 sealing Methods 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
229920003048 styrene butadiene rubber Polymers 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
MZIYQMVHASXABC-UHFFFAOYSA-N tetrakis(ethenyl)stannane Chemical compound C=C[Sn](C=C)(C=C)C=C MZIYQMVHASXABC-UHFFFAOYSA-N 0.000 description 1
CRHIAMBJMSSNNM-UHFFFAOYSA-N tetraphenylstannane Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CRHIAMBJMSSNNM-UHFFFAOYSA-N 0.000 description 1
QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
WVMSIBFANXCZKT-UHFFFAOYSA-N triethyl(hydroxy)silane Chemical compound CC[Si](O)(CC)CC WVMSIBFANXCZKT-UHFFFAOYSA-N 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

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
- C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Polymerization Catalysts (AREA)
Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)

CA308,454A 1977-09-16 1978-07-31 Copolymeres a structure desordonnee de dicyclopentadienes et de composes monocycliques insatures Expired CA1108797A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US83385077A	1977-09-16	1977-09-16
US833,850		1992-02-11

Publications (1)

Publication Number	Publication Date
CA1108797A true CA1108797A (fr)	1981-09-08

Family

ID=25265436

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA308,454A Expired CA1108797A (fr)	1977-09-16	1978-07-31	Copolymeres a structure desordonnee de dicyclopentadienes et de composes monocycliques insatures

Country Status (10)

Country	Link
JP (1)	JPS5454200A (fr)
BE (1)	BE869987A (fr)
BR (1)	BR7805927A (fr)
CA (1)	CA1108797A (fr)
DE (1)	DE2838304A1 (fr)
FR (1)	FR2403352A1 (fr)
GB (1)	GB2005280B (fr)
IT (1)	IT1107698B (fr)
MX (1)	MX147648A (fr)
NL (1)	NL7808808A (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4400340A (en) *	1982-01-25	1983-08-23	Hercules Incorporated	Method for making a dicyclopentadiene thermoset polymer
US4701510A (en) *	1985-12-16	1987-10-20	The B.F. Goodrich Company	Polycycloolefins resistant to solvents
GB8822911D0 (en) *	1988-09-29	1988-11-02	Shell Int Research	Polymerization of norbornene derivatives & catalytic system suitable for use therein
US5248745A (en) *	1988-11-22	1993-09-28	Shell Oil Company	Copolymerization of dicyclopentadiene with norbornene derivatives
GB8827320D0 (en) *	1988-11-23	1988-12-29	Shell Int Research	Process for polymerization of structurally different monomers
GB9117744D0 (en) *	1991-08-16	1991-10-02	Shell Int Research	Polymerization of cycloolefins and catalytic system suitable for use therein
DE10393129T5 (de) *	2002-08-16	2005-09-01	Johnson & Johnson Vision Care, Inc., Jacksonville	Formen für die Herstellung von Kontaktlinsen
US11724250B2 (en)	2018-09-20	2023-08-15	Exxonmobil Chemical Patents Inc.	Metathesis catalyst system for polymerizing cycloolefins
WO2021188332A1 (fr) *	2020-03-19	2021-09-23	The Board Of Trustees Of The University Of Illinois	Élastomère à propriétés ajustables et procédé de formation rapide de l'élastomère

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1029897A (fr) *	1973-11-05	1978-04-18	Robert J. Minchak	Synthese de copolymeres de cyclopentene et de dicyclopentadiene en presence d'une olefine acylique non conjuguee
CA1053850A (fr) *	1975-01-02	1979-05-01	Anthony J. Bell	Procede pour la preparation d'elastomeres de type cyclorene
CA1074949A (fr) *	1975-04-03	1980-04-01	B.F. Goodrich Company (The)	Preparation de copolymeres de cyclopentene et de dicyclopentadiene
FR2333816A1 (fr) *	1975-12-05	1977-07-01	Goodyear Tire & Rubber	Procede de preparation de polyalcenameres a forte teneur en doubles liaisons cis

1978
- 1978-07-31 CA CA308,454A patent/CA1108797A/fr not_active Expired
- 1978-08-11 GB GB7833140A patent/GB2005280B/en not_active Expired
- 1978-08-23 FR FR7824472A patent/FR2403352A1/fr active Granted
- 1978-08-25 BE BE190083A patent/BE869987A/fr not_active IP Right Cessation
- 1978-08-25 NL NL7808808A patent/NL7808808A/xx not_active Application Discontinuation
- 1978-09-01 DE DE19782838304 patent/DE2838304A1/de not_active Withdrawn
- 1978-09-08 MX MX174818A patent/MX147648A/es unknown
- 1978-09-11 IT IT51038/78A patent/IT1107698B/it active
- 1978-09-12 BR BR7805927A patent/BR7805927A/pt unknown
- 1978-09-14 JP JP11351278A patent/JPS5454200A/ja active Pending

Also Published As

Publication number	Publication date
JPS5454200A (en)	1979-04-28
MX147648A (es)	1982-12-30
GB2005280A (en)	1979-04-19
IT7851038A0 (it)	1978-09-11
BR7805927A (pt)	1979-05-02
FR2403352A1 (fr)	1979-04-13
DE2838304A1 (de)	1979-03-29
BE869987A (fr)	1978-12-18
IT1107698B (it)	1985-11-25
FR2403352B1 (fr)	1980-07-18
GB2005280B (en)	1982-03-17
NL7808808A (nl)	1979-03-20

Legal Events

Date	Code	Title	Description
1998-09-08	MKEX	Expiry

Publication	Publication Date	Title
CA1061047A (fr)	1979-08-21	Procede pour la polymerisation de la norbornene avec le dicyclopentadiene, avec formation de tres peu de gel
US4002815A (en)	1977-01-11	Cyclopentene-dicyclopentadiene copolymers and method of making same
CA1115895A (fr)	1982-01-05	Copolymeres d'alkylnorbornene a cycle ouvert
EP0002278B1 (fr)	1983-09-07	Copolymérisation du diméthylnorbornène et de l'isopropylnorbornène par ouverture du cycle
US3804803A (en)	1974-04-16	Polyalkenamers and process for the preparation thereof
CA1115896A (fr)	1982-01-05	Copolymeres a chaines ouvertes de dihydrodicyclopentadiene et de norbornene ou d'alkylnorbornene et d'une olefine acyclique
CA1064009A (fr)	1979-10-09	Methode de polymerisation de diolefines conjuguees basee sur l'utilisation de catalyseurs au fer et de complexes azotes
US3798175A (en)	1974-03-19	Catalysts for the ring opening polymerization of cyclic olefins
JPS591508A (ja)	1984-01-06	共役ジエン重合のための触媒
CA1108797A (fr)	1981-09-08	Copolymeres a structure desordonnee de dicyclopentadienes et de composes monocycliques insatures
US3549607A (en)	1970-12-22	High cis polypentenamers
CA1074949A (fr)	1980-04-01	Preparation de copolymeres de cyclopentene et de dicyclopentadiene
US3471462A (en)	1969-10-07	Catalytic production of polybutadiene and catalysts therefor
CA1116792A (fr)	1982-01-19	Procede de preparation de polymeres a partir de melanges de cyclopentadiene et de bicycloheptene
US3816382A (en)	1974-06-11	Polyalkenamers and process for the preparation thereof
US3597403A (en)	1971-08-03	Novel catalysts for the ring-opening polymerization of unsaturated alicyclic compounds
US3853830A (en)	1974-12-10	Process for preparing polymers of cyclopentene
US4025708A (en)	1977-05-24	Process for polymerizing cyclopentene
US3247175A (en)	1966-04-19	Process for preparing high cis-1, 4-polybutadiene
US3849509A (en)	1974-11-19	Polyalkenamers and process for the preparation thereof
US5595951A (en)	1997-01-21	Process for preparing a multilithio initiator for improved tire rubbers
CA1134098A (fr)	1982-10-19	Copolymeres solubles dans les hydrocarbures de bicycloheptenes et de 1,3-butadiene
CA1134550A (fr)	1982-10-26	Procede de copolymerisation du cyclopentene
US3577400A (en)	1971-05-04	Novel catalysts for the polymerization of alicyclic olefins
US3772255A (en)	1973-11-13	Ring-opening polymerization of cycloolefins