CA2056209A1 - Solutions de reaction polymerisables en masse - Google Patents

Solutions de reaction polymerisables en masse

Info

Publication number: CA2056209A1
Authority: CA; Canada
Prior art keywords: norbornene; reaction solution; group; monomer; mixtures
Prior art date: 1990-11-28
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 2056209

Other languages

English (en)

Inventor

Kin-Ichi Okumura

Hirotoshi Tanimoto

Tomoo Sugawara

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.)

Zeon Corp

Original Assignee

Individual

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.)

1990-11-28

Filing date

1991-11-26

Publication date

1992-05-29

1991-11-26 Application filed by Individual filed Critical Individual

1992-05-29 Publication of CA2056209A1 publication Critical patent/CA2056209A1/fr

Status Abandoned legal-status Critical Current

Links

238000006243 chemical reaction Methods 0.000 title claims abstract description 48
239000000178 monomer Substances 0.000 claims abstract description 61
239000003054 catalyst Substances 0.000 claims abstract description 42
238000005649 metathesis reaction Methods 0.000 claims abstract description 27
239000003795 chemical substances by application Substances 0.000 claims abstract description 20
230000003213 activating effect Effects 0.000 claims abstract description 19
150000004820 halides Chemical class 0.000 claims abstract description 12
239000010936 titanium Substances 0.000 claims abstract description 9
229910052719 titanium Inorganic materials 0.000 claims abstract description 9
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 7
JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims abstract description 7
239000000203 mixture Substances 0.000 claims description 30
238000000034 method Methods 0.000 claims description 22
239000000376 reactant Substances 0.000 claims description 22
-1 TiH4 Chemical compound 0.000 claims description 15
MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 claims description 11
HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical group C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
150000001875 compounds Chemical class 0.000 claims description 9
229910052750 molybdenum Inorganic materials 0.000 claims description 9
238000006116 polymerization reaction Methods 0.000 claims description 9
PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 claims description 9
229910052721 tungsten Inorganic materials 0.000 claims description 9
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical class [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
239000011733 molybdenum Substances 0.000 claims description 8
239000010937 tungsten Chemical class 0.000 claims description 8
238000012662 bulk polymerization Methods 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical class [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 7
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 6
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 6
GDSGXRQXKTWBOS-UHFFFAOYSA-N n,n-di(tridecyl)tridecan-1-amine Chemical compound CCCCCCCCCCCCCN(CCCCCCCCCCCCC)CCCCCCCCCCCCC GDSGXRQXKTWBOS-UHFFFAOYSA-N 0.000 claims description 6
ABVVEAHYODGCLZ-UHFFFAOYSA-O tridecylazanium Chemical compound CCCCCCCCCCCCC[NH3+] ABVVEAHYODGCLZ-UHFFFAOYSA-O 0.000 claims description 6
XTAZYLNFDRKIHJ-UHFFFAOYSA-O trioctylazanium Chemical compound CCCCCCCC[NH+](CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-O 0.000 claims description 6
239000011609 ammonium molybdate Substances 0.000 claims description 5
229940010552 ammonium molybdate Drugs 0.000 claims description 5
235000018660 ammonium molybdate Nutrition 0.000 claims description 5
150000003863 ammonium salts Chemical class 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
150000002367 halogens Chemical group 0.000 claims description 4
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 4
150000003755 zirconium compounds Chemical class 0.000 claims description 4
OJOWICOBYCXEKR-APPZFPTMSA-N (1S,4R)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound CC=C1C[C@@H]2C[C@@H]1C=C2 OJOWICOBYCXEKR-APPZFPTMSA-N 0.000 claims description 3
YSWATWCBYRBYBO-UHFFFAOYSA-N 5-butylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCC)CC1C=C2 YSWATWCBYRBYBO-UHFFFAOYSA-N 0.000 claims description 3
PSCJIEZOAFAQRM-UHFFFAOYSA-N 5-chlorobicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(Cl)CC1C=C2 PSCJIEZOAFAQRM-UHFFFAOYSA-N 0.000 claims description 3
QHJIJNGGGLNBNJ-UHFFFAOYSA-N 5-ethylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CC)CC1C=C2 QHJIJNGGGLNBNJ-UHFFFAOYSA-N 0.000 claims description 3
WMWDGZLDLRCDRG-UHFFFAOYSA-N 5-hexylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCC)CC1C=C2 WMWDGZLDLRCDRG-UHFFFAOYSA-N 0.000 claims description 3
PCBPVYHMZBWMAZ-UHFFFAOYSA-N 5-methylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C)CC1C=C2 PCBPVYHMZBWMAZ-UHFFFAOYSA-N 0.000 claims description 3
PGNNHYNYFLXKDZ-UHFFFAOYSA-N 5-phenylbicyclo[2.2.1]hept-2-ene Chemical compound C1=CC2CC1CC2C1=CC=CC=C1 PGNNHYNYFLXKDZ-UHFFFAOYSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
229910010342 TiF4 Inorganic materials 0.000 claims description 3
229910007998 ZrF4 Inorganic materials 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000004104 aryloxy group Chemical group 0.000 claims description 3
BMAXQTDMWYDIJX-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-5-carbonitrile Chemical compound C1C2C(C#N)CC1C=C2 BMAXQTDMWYDIJX-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-UHFFFAOYSA-N 0.000 claims description 3
HYPABJGVBDSCIT-UPHRSURJSA-N cyclododecene Chemical compound C1CCCCC\C=C/CCCC1 HYPABJGVBDSCIT-UPHRSURJSA-N 0.000 claims description 3
URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 claims description 3
239000004913 cyclooctene Substances 0.000 claims description 3
JAGHDVYKBYUAFD-UHFFFAOYSA-L cyclopenta-1,3-diene;titanium(4+);dichloride Chemical compound [Cl-].[Cl-].[Ti+4].C1C=CC=[C-]1.C1C=CC=[C-]1 JAGHDVYKBYUAFD-UHFFFAOYSA-L 0.000 claims description 3
HANKSFAYJLDDKP-UHFFFAOYSA-N dihydrodicyclopentadiene Chemical compound C12CC=CC2C2CCC1C2 HANKSFAYJLDDKP-UHFFFAOYSA-N 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
UCQHUEOREKHIBP-UHFFFAOYSA-N heptacyclo[9.6.1.14,7.113,16.02,10.03,8.012,17]icosa-5,14-diene Chemical compound C1C(C23)C4C(C=C5)CC5C4C1C3CC1C2C2C=CC1C2 UCQHUEOREKHIBP-UHFFFAOYSA-N 0.000 claims description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
RMAZRAQKPTXZNL-UHFFFAOYSA-N methyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2C(C(=O)OC)CC1C=C2 RMAZRAQKPTXZNL-UHFFFAOYSA-N 0.000 claims description 3
SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 claims description 3
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 3
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 description 3
UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 claims description 3
XROWMBWRMNHXMF-UHFFFAOYSA-J titanium tetrafluoride Chemical compound [F-].[F-].[F-].[F-].[Ti+4] XROWMBWRMNHXMF-UHFFFAOYSA-J 0.000 claims description 3
OMQSJNWFFJOIMO-UHFFFAOYSA-J zirconium tetrafluoride Chemical compound F[Zr](F)(F)F OMQSJNWFFJOIMO-UHFFFAOYSA-J 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
YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 claims description 2
229910010068 TiCl2 Inorganic materials 0.000 claims 2
229910010062 TiCl3 Inorganic materials 0.000 claims 2
229910003074 TiCl4 Inorganic materials 0.000 claims 2
229910010386 TiI4 Inorganic materials 0.000 claims 2
NLLZTRMHNHVXJJ-UHFFFAOYSA-J titanium tetraiodide Chemical compound I[Ti](I)(I)I NLLZTRMHNHVXJJ-UHFFFAOYSA-J 0.000 claims 2
ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 claims 2
YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 claims 2
FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 claims 1
229910007932 ZrCl4 Inorganic materials 0.000 claims 1
229960005235 piperonyl butoxide Drugs 0.000 claims 1
230000000379 polymerizing effect Effects 0.000 claims 1
DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 claims 1
229910052726 zirconium Inorganic materials 0.000 abstract description 6
230000002411 adverse Effects 0.000 abstract description 4
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 abstract 1
239000000243 solution Substances 0.000 description 38
239000000047 product Substances 0.000 description 12
229920000642 polymer Polymers 0.000 description 9
238000005260 corrosion Methods 0.000 description 8
230000007797 corrosion Effects 0.000 description 8
239000000835 fiber Substances 0.000 description 8
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Substances 0.000 description 8
238000009472 formulation Methods 0.000 description 6
239000003963 antioxidant agent Substances 0.000 description 5
230000009257 reactivity Effects 0.000 description 5
239000012779 reinforcing material Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
229910052782 aluminium Inorganic materials 0.000 description 4
238000005452 bending Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000003365 glass fiber Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
229920000346 polystyrene-polyisoprene block-polystyrene Polymers 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
239000011347 resin Substances 0.000 description 4
229920005989 resin Polymers 0.000 description 4
229910000975 Carbon steel Inorganic materials 0.000 description 3
239000000654 additive Substances 0.000 description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
230000003078 antioxidant effect Effects 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
239000010962 carbon steel Substances 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
229920001971 elastomer Polymers 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
230000008569 process Effects 0.000 description 3
238000010107 reaction injection moulding Methods 0.000 description 3
230000000391 smoking effect Effects 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 3
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 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
229920002943 EPDM rubber Polymers 0.000 description 2
239000005062 Polybutadiene Substances 0.000 description 2
239000012190 activator Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
239000000806 elastomer Substances 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000003517 fume Substances 0.000 description 2
239000000499 gel Substances 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000000463 material Substances 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
229920002857 polybutadiene Polymers 0.000 description 2
230000002787 reinforcement Effects 0.000 description 2
229910052710 silicon Inorganic materials 0.000 description 2
239000005049 silicon tetrachloride Substances 0.000 description 2
239000000779 smoke Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
229920003048 styrene butadiene rubber Polymers 0.000 description 2
229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 2
229910052718 tin Inorganic materials 0.000 description 2
PYSUIEFOHAWWDU-UHFFFAOYSA-L 2-propoxyethylaluminum(2+);dichloride Chemical compound [Cl-].[Cl-].CCCOCC[Al+2] PYSUIEFOHAWWDU-UHFFFAOYSA-L 0.000 description 1
OBYOFMNDYOOIPV-UHFFFAOYSA-N 3-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C=C1C(C)(C)C OBYOFMNDYOOIPV-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
CSRQAJIMYJHHHQ-UHFFFAOYSA-N 9-ethylidenetetracyclo[6.2.1.13,6.02,7]dodec-4-ene Chemical compound C1C(C23)C=CC1C3C1CC2CC1=CC CSRQAJIMYJHHHQ-UHFFFAOYSA-N 0.000 description 1
239000004925 Acrylic resin Substances 0.000 description 1
229920000178 Acrylic resin Polymers 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
229920000049 Carbon (fiber) Polymers 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
244000043261 Hevea brasiliensis Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
235000010678 Paulownia tomentosa Nutrition 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
229910003910 SiCl4 Inorganic materials 0.000 description 1
239000006087 Silane Coupling Agent Substances 0.000 description 1
229910008046 SnC14 Inorganic materials 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
239000002174 Styrene-butadiene Substances 0.000 description 1
229910010061 TiC13 Inorganic materials 0.000 description 1
229910010066 TiC14 Inorganic materials 0.000 description 1
244000153888 Tung Species 0.000 description 1
239000004699 Ultra-high molecular weight polyethylene Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000004760 aramid Substances 0.000 description 1
229920006231 aramid fiber Polymers 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
239000004917 carbon fiber Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000011109 contamination Methods 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
NJLLQSBAHIKGKF-UHFFFAOYSA-N dipotassium dioxido(oxo)titanium Chemical compound [K+].[K+].[O-][Ti]([O-])=O NJLLQSBAHIKGKF-UHFFFAOYSA-N 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000003063 flame retardant Substances 0.000 description 1
239000004088 foaming agent Substances 0.000 description 1
229910052732 germanium Inorganic materials 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000009477 glass transition Effects 0.000 description 1
239000011964 heteropoly acid Chemical class 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229920003052 natural elastomer Polymers 0.000 description 1
229920001194 natural rubber Polymers 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920001195 polyisoprene Polymers 0.000 description 1
230000037048 polymerization activity Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002028 premature Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
239000012744 reinforcing agent Substances 0.000 description 1
238000007151 ring opening polymerisation reaction Methods 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
239000005060 rubber Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000010703 silicon Substances 0.000 description 1
HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
229910010271 silicon carbide Inorganic materials 0.000 description 1
FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000002411 thermogravimetry Methods 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
229920000785 ultra high molecular weight polyethylene Polymers 0.000 description 1
238000009834 vaporization Methods 0.000 description 1
230000008016 vaporization Effects 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000002023 wood Substances 0.000 description 1

Landscapes

Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)

CA 2056209 1990-11-28 1991-11-26 Solutions de reaction polymerisables en masse Abandoned CA2056209A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP3311590		1990-11-28
JP2-33115		1990-11-28

Publications (1)

Publication Number	Publication Date
CA2056209A1 true CA2056209A1 (fr)	1992-05-29

Family

ID=12377643

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2056209 Abandoned CA2056209A1 (fr)	1990-11-28	1991-11-26	Solutions de reaction polymerisables en masse

Country Status (1)

Country	Link
CA (1)	CA2056209A1 (fr)

1991
- 1991-11-26 CA CA 2056209 patent/CA2056209A1/fr not_active Abandoned

Legal Events

Date	Code	Title	Description
1996-05-26	FZDE	Dead

Publication	Publication Date	Title
JP2933952B2 (ja)	1999-08-16	保存安定性に優れたシクロオレフィンのバルク重合用共触媒含有原料の製法、およびバルク重合法
JPH05222168A (ja)	1993-08-31	反応射出成形用反応原液
KR0179039B1 (ko)	1999-05-15	필름성형용 고결정성 폴리프로필렌
JPH0613564B2 (ja)	1994-02-23	耐衝撃性が改良されたポリシクロオレフィン成形体およびその製造法
JPH0557288B2 (fr)	1993-08-23
US4808635A (en)	1989-02-28	Method for making a dicyclopentadiene cross-linked polymer and the product thereof
IE914107A1 (en)	1992-06-03	Bulk polymerizable reaction solutions
EP0281086B1 (fr)	1994-04-20	Alliages de polymères polycyclo-oléfine utilisant des polymères fonctionnels dispersés à base d'éthylène
US5204427A (en)	1993-04-20	Method of making ring-opened polynorbornene polymers using pot life extending agents
CA1258745A (fr)	1989-08-22	Methode d'obtention d'un polymere de dicyclopentadiene reticule
CA2056209A1 (fr)	1992-05-29	Solutions de reaction polymerisables en masse
EP0269948B1 (fr)	1995-03-22	Procédé pour préparer des polycyclo-oléfines modifiées
US3830877A (en)	1974-08-20	Copolyalkenamers having a sequential structure,and method for preparing same
EP0534482B1 (fr)	1997-07-23	Système de catalysateur métathesis
KR970001540B1 (ko)	1997-02-11	열 경화성 수지의 제조방법
EP0324979B1 (fr)	1994-03-23	Mélange de norbornène à durée d'emploi prolongée
JPS61293208A (ja)	1986-12-24	開環共重合体の製造方法
US5438093A (en)	1995-08-01	Modified polycycloolefins
EP0426142B1 (fr)	1995-09-20	Procédé de préparation, par ouverture de cycle, de polymères de norbornène utilisant des agents de stabilisation à l'entreposage
US4853435A (en)	1989-08-01	Process for preparing thermosetting resin
JPH04279628A (ja)	1992-10-05	ノルボルネン系ポリマーの製造方法
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
EP0585887A2 (fr)	1994-03-09	Système catalytique de métathèse activé
JP2892714B2 (ja)	1999-05-17	強化ノルボルネン系ポリマーの製造方法
JPH03146516A (ja)	1991-06-21	ノルボルネン系ポリマーの製造方法