CA1215073A - CATALYST ACTIVATOR FOR .alpha. OLEFIN POLYMERIZATION - Google Patents
CATALYST ACTIVATOR FOR .alpha. OLEFIN POLYMERIZATIONInfo
- Publication number
- CA1215073A CA1215073A CA000443256A CA443256A CA1215073A CA 1215073 A CA1215073 A CA 1215073A CA 000443256 A CA000443256 A CA 000443256A CA 443256 A CA443256 A CA 443256A CA 1215073 A CA1215073 A CA 1215073A
- Authority
- CA
- Canada
- Prior art keywords
- chlorine
- hydrogen
- bromine
- compound
- alkyl
- Prior art date
- 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
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 47
- 238000006116 polymerization reaction Methods 0.000 title claims description 23
- 239000012190 activator Substances 0.000 title description 26
- 150000001336 alkenes Chemical class 0.000 title 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title 1
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 63
- 239000000460 chlorine Substances 0.000 claims abstract description 63
- 239000001257 hydrogen Substances 0.000 claims abstract description 59
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 59
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 39
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 26
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 23
- 230000008569 process Effects 0.000 claims abstract description 18
- 125000006575 electron-withdrawing group Chemical group 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 229910052720 vanadium Inorganic materials 0.000 claims abstract description 5
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims abstract description 3
- 229910052794 bromium Chemical group 0.000 claims abstract 28
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract 27
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract 27
- 125000000217 alkyl group Chemical group 0.000 claims abstract 6
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims abstract 5
- 125000002947 alkylene group Chemical group 0.000 claims abstract 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 5
- 238000004519 manufacturing process Methods 0.000 claims abstract 3
- 229920013639 polyalphaolefin Polymers 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- -1 dimethyl 2-trichloromethylbut-2-endioate Chemical compound 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 10
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 8
- 239000002879 Lewis base Substances 0.000 claims description 6
- 150000007527 lewis bases Chemical class 0.000 claims description 6
- UFMFLFREEKBUDS-UHFFFAOYSA-N 2-ethylhexyl 4,4,4-trichlorobut-2-enoate Chemical compound CCCCC(CC)COC(=O)C=CC(Cl)(Cl)Cl UFMFLFREEKBUDS-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- PTQHHFNTRMFDLV-UHFFFAOYSA-N methyl 4,4,4-trichlorobut-2-enoate Chemical compound COC(=O)C=CC(Cl)(Cl)Cl PTQHHFNTRMFDLV-UHFFFAOYSA-N 0.000 claims description 4
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims description 3
- 230000003213 activating effect Effects 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims description 3
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 3
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- SNFGYHXDYWUXIA-UHFFFAOYSA-N methyl 4,4,4-trichloro-2-methylbut-2-enoate Chemical compound COC(=O)C(C)=CC(Cl)(Cl)Cl SNFGYHXDYWUXIA-UHFFFAOYSA-N 0.000 claims description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- 101100277337 Arabidopsis thaliana DDM1 gene Proteins 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 101150113676 chr1 gene Proteins 0.000 claims description 2
- WIWBLJMBLGWSIN-UHFFFAOYSA-L dichlorotris(triphenylphosphine)ruthenium(ii) Chemical compound [Cl-].[Cl-].[Ru+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 WIWBLJMBLGWSIN-UHFFFAOYSA-L 0.000 claims description 2
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims description 2
- IZIBACDHNNVHQA-UHFFFAOYSA-N ethyl 4,4,4-trichlorobut-2-enoate Chemical compound CCOC(=O)C=CC(Cl)(Cl)Cl IZIBACDHNNVHQA-UHFFFAOYSA-N 0.000 claims description 2
- 230000006872 improvement Effects 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 239000002685 polymerization catalyst Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- YKQFRTQUUWZPEP-VOTSOKGWSA-N butyl (E)-4,4,4-trichloro-2-methylbut-2-enoate Chemical compound CCCCOC(=O)C(\C)=C\C(Cl)(Cl)Cl YKQFRTQUUWZPEP-VOTSOKGWSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 230000036647 reaction Effects 0.000 claims 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 abstract description 2
- 229940074995 bromine Drugs 0.000 abstract 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 28
- 150000002431 hydrogen Chemical class 0.000 description 24
- 229920000642 polymer Polymers 0.000 description 22
- 229920000180 alkyd Polymers 0.000 description 15
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 13
- 239000004711 α-olefin Substances 0.000 description 12
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- SHXWCVYOXRDMCX-UHFFFAOYSA-N 3,4-methylenedioxymethamphetamine Chemical compound CNC(C)CC1=CC=C2OCOC2=C1 SHXWCVYOXRDMCX-UHFFFAOYSA-N 0.000 description 8
- 229920002943 EPDM rubber Polymers 0.000 description 8
- 241000110847 Kochia Species 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 7
- 239000005977 Ethylene Substances 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 229950005499 carbon tetrachloride Drugs 0.000 description 6
- 125000001495 ethyl group Chemical class [H]C([H])([H])C([H])([H])* 0.000 description 5
- 230000011514 reflex Effects 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 230000001755 vocal effect Effects 0.000 description 4
- MZTRYMYPEIBMGG-UHFFFAOYSA-M 2-bromo-3,4-dimethyl-1,3-thiazol-3-ium;bromide Chemical compound [Br-].CC1=CSC(Br)=[N+]1C MZTRYMYPEIBMGG-UHFFFAOYSA-M 0.000 description 3
- 241000282320 Panthera leo Species 0.000 description 3
- 208000037062 Polyps Diseases 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000011345 viscous material Substances 0.000 description 3
- RWUHMISXOUGVKX-OWOJBTEDSA-N (e)-2,3,4,4,4-pentachlorobut-2-enoic acid Chemical compound OC(=O)C(\Cl)=C(/Cl)C(Cl)(Cl)Cl RWUHMISXOUGVKX-OWOJBTEDSA-N 0.000 description 2
- 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 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 2
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- VAGAHQGPIKRLLK-UHFFFAOYSA-N diplamine Chemical compound C1=NC(C(C(SC)=C2CCNC(C)=O)=O)=C3C2=NC2=CC=CC=C2C3=C1 VAGAHQGPIKRLLK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000001052 transient effect Effects 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- ZWVMLYRJXORSEP-LURJTMIESA-N (2s)-hexane-1,2,6-triol Chemical compound OCCCC[C@H](O)CO ZWVMLYRJXORSEP-LURJTMIESA-N 0.000 description 1
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical class CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 description 1
- NXERUYGRZMHUMK-UHFFFAOYSA-N 4,4,4-trichlorobut-2-enoic acid Chemical compound OC(=O)C=CC(Cl)(Cl)Cl NXERUYGRZMHUMK-UHFFFAOYSA-N 0.000 description 1
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 241000700115 Myocastoridae Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 1
- 239000002253 acid Substances 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
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- XNNQFQFUQLJSQT-UHFFFAOYSA-N bromo(trichloro)methane Chemical compound ClC(Cl)(Cl)Br XNNQFQFUQLJSQT-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- GGNALUCSASGNCK-UHFFFAOYSA-N carbon dioxide;propan-2-ol Chemical compound O=C=O.CC(C)O GGNALUCSASGNCK-UHFFFAOYSA-N 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007269 dehydrobromination reaction Methods 0.000 description 1
- LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 description 1
- 229960004419 dimethyl fumarate Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229930190788 diplamine Natural products 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 229920001198 elastomeric copolymer Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 150000002681 magnesium compounds Chemical class 0.000 description 1
- 238000004890 malting Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229940082615 organic nitrates used in cardiac disease Drugs 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000002311 subsequent effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Landscapes
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44936882A | 1982-12-14 | 1982-12-14 | |
| US44981182A | 1982-12-14 | 1982-12-14 | |
| US449,368 | 1982-12-14 | ||
| US449,811 | 1982-12-14 | ||
| US52802083A | 1983-08-31 | 1983-08-31 | |
| US52820283A | 1983-08-31 | 1983-08-31 | |
| US528,202 | 1983-08-31 | ||
| US528,020 | 1990-05-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1215073A true CA1215073A (en) | 1986-12-09 |
Family
ID=27503969
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000443256A Expired CA1215073A (en) | 1982-12-14 | 1983-12-14 | CATALYST ACTIVATOR FOR .alpha. OLEFIN POLYMERIZATION |
| CA000443255A Expired CA1242550A (en) | 1982-12-14 | 1983-12-14 | Catalyst for alpha-olefin polymerization |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000443255A Expired CA1242550A (en) | 1982-12-14 | 1983-12-14 | Catalyst for alpha-olefin polymerization |
Country Status (4)
| Country | Link |
|---|---|
| AU (2) | AU573196B2 (enrdf_load_stackoverflow) |
| BR (2) | BR8306822A (enrdf_load_stackoverflow) |
| CA (2) | CA1215073A (enrdf_load_stackoverflow) |
| IN (2) | IN160181B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5786504A (en) * | 1996-05-15 | 1998-07-28 | Uniroyal Chemical Company, Inc. | Polymerization catalyst promoter |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2640978B1 (enrdf_load_stackoverflow) * | 1988-12-22 | 1991-04-19 | Bp Chimie Sa |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU459046B2 (en) * | 1970-08-11 | 1975-03-13 | Ciba-Geigy Ag | Process forthe manufacture of tertiary butylates |
| US4189558A (en) * | 1977-02-14 | 1980-02-19 | Bayer Aktiengesellschaft | Process for the production of butadiene-propylene copolymers |
| DE2933885C3 (de) * | 1979-08-22 | 1982-05-06 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur Herstellung von Copolymeren des Ethylens mit mindestens einem anderen 1-Monoolefin und ggf. einem nicht-konjugierten Dien |
| AU1587683A (en) * | 1983-06-17 | 1984-12-20 | Merck & Co., Inc. | 2,3-dihalo-2,3-disubstituted propanoates |
-
1983
- 1983-12-05 IN IN818/DEL/83A patent/IN160181B/en unknown
- 1983-12-05 IN IN819/DEL/83A patent/IN160356B/en unknown
- 1983-12-05 AU AU21990/83A patent/AU573196B2/en not_active Ceased
- 1983-12-05 AU AU21989/83A patent/AU575547B2/en not_active Ceased
- 1983-12-12 BR BR8306822A patent/BR8306822A/pt unknown
- 1983-12-12 BR BR8306821A patent/BR8306821A/pt not_active IP Right Cessation
- 1983-12-14 CA CA000443256A patent/CA1215073A/en not_active Expired
- 1983-12-14 CA CA000443255A patent/CA1242550A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5786504A (en) * | 1996-05-15 | 1998-07-28 | Uniroyal Chemical Company, Inc. | Polymerization catalyst promoter |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2199083A (en) | 1984-06-21 |
| AU2198983A (en) | 1984-06-21 |
| BR8306822A (pt) | 1984-11-13 |
| AU573196B2 (en) | 1988-06-02 |
| CA1242550A (en) | 1988-09-27 |
| BR8306821A (pt) | 1984-11-13 |
| IN160181B (enrdf_load_stackoverflow) | 1987-06-27 |
| AU575547B2 (en) | 1988-08-04 |
| IN160356B (enrdf_load_stackoverflow) | 1987-07-11 |
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Legal Events
| Date | Code | Title | Description |
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| MKEX | Expiry |