CA1053850A - Procede pour la preparation d'elastomeres de type cyclorene - Google Patents

Procede pour la preparation d'elastomeres de type cyclorene

Info

Publication number: CA1053850A
Authority: CA; Canada
Prior art keywords: group; cyclopolyene; compound; carbon atoms; chlorine
Prior art date: 1975-01-02
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

CA240,398A

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.)

1975-01-02

Filing date

1975-11-25

Publication date

1979-05-01

1975-11-25 Application filed by Goodyear Tire and Rubber Co filed Critical Goodyear Tire and Rubber Co

1979-05-01 Application granted granted Critical

1979-05-01 Publication of CA1053850A publication Critical patent/CA1053850A/fr

Status Expired legal-status Critical Current

Links

229920001971 elastomer Polymers 0.000 title abstract description 6
239000000806 elastomer Substances 0.000 title abstract 2
238000004519 manufacturing process Methods 0.000 title abstract 2
239000003054 catalyst Substances 0.000 claims abstract description 22
239000000460 chlorine Substances 0.000 claims abstract description 18
238000005865 alkene metathesis reaction Methods 0.000 claims abstract description 11
150000001875 compounds Chemical class 0.000 claims abstract description 10
238000000034 method Methods 0.000 claims abstract description 10
229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 8
VUNCWTMEJYMOOR-UHFFFAOYSA-N hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-UHFFFAOYSA-N 0.000 claims abstract description 8
238000010438 heat treatment Methods 0.000 claims abstract description 7
238000011065 in-situ storage Methods 0.000 claims abstract description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 17
-1 tungsten halide salt Chemical class 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 8
229910052782 aluminium Inorganic materials 0.000 claims description 7
229910052721 tungsten Inorganic materials 0.000 claims description 7
239000010937 tungsten Substances 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
150000002736 metal compounds Chemical class 0.000 claims description 3
239000003381 stabilizer Substances 0.000 claims description 3
AFCAKJKUYFLYFK-UHFFFAOYSA-N tetrabutyltin Chemical compound CCCC[Sn](CCCC)(CCCC)CCCC AFCAKJKUYFLYFK-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
ZOLLIQAKMYWTBR-RYMQXAEESA-N cyclododecatriene Chemical compound C/1C\C=C\CC\C=C/CC\C=C\1 ZOLLIQAKMYWTBR-RYMQXAEESA-N 0.000 claims description 2
125000004438 haloalkoxy group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000005386 organosiloxy group Chemical group 0.000 claims description 2
KEMUGHMYINTXKW-NQOXHWNZSA-N (1z,5z)-cyclododeca-1,5-diene Chemical compound C1CCC\C=C/CC\C=C/CC1 KEMUGHMYINTXKW-NQOXHWNZSA-N 0.000 claims 1
HQGYGGZHZWXFSI-UHFFFAOYSA-N 1,4-cycloheptadiene Chemical compound C1CC=CCC=C1 HQGYGGZHZWXFSI-UHFFFAOYSA-N 0.000 claims 1
VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 claims 1
239000004912 1,5-cyclooctadiene Substances 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
238000006116 polymerization reaction Methods 0.000 description 8
239000000243 solution Substances 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 5
229960004132 diethyl ether Drugs 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
238000007151 ring opening polymerisation reaction Methods 0.000 description 5
QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000000178 monomer Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
150000001925 cycloalkenes Chemical class 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000014759 maintenance of location Effects 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000007142 ring opening reaction Methods 0.000 description 2
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
SXIFNAOBIAIYJO-SXVCMZJPSA-N (1E,3E,7E)-cyclododeca-1,3,7-triene Chemical compound C/1=C\CCCC\C=C\C=C\CC\1 SXIFNAOBIAIYJO-SXVCMZJPSA-N 0.000 description 1
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical compound CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
GAXYCNAZQSPXMB-UHFFFAOYSA-K CCO[W](Cl)(Cl)(Cl)(OCC)OCC Chemical compound CCO[W](Cl)(Cl)(Cl)(OCC)OCC GAXYCNAZQSPXMB-UHFFFAOYSA-K 0.000 description 1
RYMRAPBZJXNGGK-UHFFFAOYSA-H Cl[W](Cl)(Cl)(Cl)(Cl)OC1=CC=CC=C1 Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)OC1=CC=CC=C1 RYMRAPBZJXNGGK-UHFFFAOYSA-H 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
238000005698 Diels-Alder reaction Methods 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
230000001112 coagulating effect Effects 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000010528 free radical solution polymerization reaction Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
239000002685 polymerization catalyst Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical compound [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000007789 sealing Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
230000002311 subsequent effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
RWWNQEOPUOCKGR-UHFFFAOYSA-N tetraethyltin Chemical compound CC[Sn](CC)(CC)CC RWWNQEOPUOCKGR-UHFFFAOYSA-N 0.000 description 1
230000009466 transformation Effects 0.000 description 1
VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 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
238000010626 work up procedure Methods 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)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA240,398A 1975-01-02 1975-11-25 Procede pour la preparation d'elastomeres de type cyclorene Expired CA1053850A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US53804475A	1975-01-02	1975-01-02

Publications (1)

Publication Number	Publication Date
CA1053850A true CA1053850A (fr)	1979-05-01

Family

ID=24145197

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA240,398A Expired CA1053850A (fr)	1975-01-02	1975-11-25	Procede pour la preparation d'elastomeres de type cyclorene

Country Status (5)

Country	Link
JP (1)	JPS6033845B2 (fr)
CA (1)	CA1053850A (fr)
DE (1)	DE2553954A1 (fr)
GB (1)	GB1485595A (fr)
IT (1)	IT1052548B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1108797A (fr) *	1977-09-16	1981-09-08	Anthony J. Bell	Copolymeres a structure desordonnee de dicyclopentadienes et de composes monocycliques insatures

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3634374A (en) *	1969-10-01	1972-01-11	Goodyear Tire & Rubber	Polymerization of chlorine containing unsaturated polymers and products thereof

1975
- 1975-11-25 CA CA240,398A patent/CA1053850A/fr not_active Expired
- 1975-12-01 GB GB4923875A patent/GB1485595A/en not_active Expired
- 1975-12-01 DE DE19752553954 patent/DE2553954A1/de not_active Ceased
- 1975-12-09 IT IT5258775A patent/IT1052548B/it active
- 1975-12-18 JP JP50151200A patent/JPS6033845B2/ja not_active Expired

Also Published As

Publication number	Publication date
DE2553954A1 (de)	1976-07-08
JPS6033845B2 (ja)	1985-08-05
JPS5190399A (fr)	1976-08-07
GB1485595A (en)	1977-09-14
IT1052548B (it)	1981-07-20

Publication	Publication Date	Title
CA1222597A (fr)	1987-06-02	Preparation de polymeres a partir d'olefines cycliques
KR950000038B1 (ko)	1995-01-07	용매에 대한 폴리시클로 올레핀의 저항성
KR0156842B1 (ko)	1998-12-01	올레핀의 중합(삼량체화 포함)을 수행하는데 있어 촉매로서 유용한 크롬-함유 화합물의 제조방법
KR0150204B1 (ko)	1998-10-15	폴리에틸렌 및 그의 제법
US4020254A (en)	1977-04-26	Metathesis polymerization of cycloolefins
CA1045295A (fr)	1978-12-26	Double decomposition de cycloolefines
US3781257A (en)	1973-12-25	Copolymerization of cyclopentene with polycyclic polyolefines
EP0002279B1 (fr)	1983-01-26	Procédé pour préparation des polymères à partir de mélanges de cyclopentadiène et de bicycloheptène
CA1053850A (fr)	1979-05-01	Procede pour la preparation d'elastomeres de type cyclorene
US3853830A (en)	1974-12-10	Process for preparing polymers of cyclopentene
CA1103845A (fr)	1981-06-23	Procede d'obtention de copolymeres de cyclopentene et de composes alicycliques insatures
US3846392A (en)	1974-11-05	Method of manufacturing cycloolefines
US5028672A (en)	1991-07-02	Catalyst and process for polymerization of norbornene derivatives
CA2113188A1 (fr)	1993-01-21	Procede de polymerisation et produits connexes
US4137390A (en)	1979-01-30	Process for the polymerization of cycloolefins
EP0269948B1 (fr)	1995-03-22	Procédé pour préparer des polycyclo-oléfines modifiées
CA1042594A (fr)	1978-11-14	Double decomposition de cycloolefines
EP0067784B1 (fr)	1985-11-13	Catalyseurs pour la copolymérisation par ouverture du cycle de cycloalcènes
CA1087154A (fr)	1980-10-07	Polymerisation cationique
JPS5946525B2 (ja)	1984-11-13	共重合体およびその製造方法
US3966637A (en)	1976-06-29	Catalysts
US3772255A (en)	1973-11-13	Ring-opening polymerization of cycloolefins
US4415715A (en)	1983-11-15	Catalysts for ring-opening copolymerization of cycloolefins
KR920004600B1 (ko)	1992-06-11	α, ω-디인의 중합 방법
SU476282A1 (ru)	1975-07-05	Способ получени полиалкенамеров