ZA200900083B - Bulk polymerization process for producing polydienes - Google Patents
Bulk polymerization process for producing polydienes Download PDFInfo
- Publication number
- ZA200900083B ZA200900083B ZA200900083A ZA200900083A ZA200900083B ZA 200900083 B ZA200900083 B ZA 200900083B ZA 200900083 A ZA200900083 A ZA 200900083A ZA 200900083 A ZA200900083 A ZA 200900083A ZA 200900083 B ZA200900083 B ZA 200900083B
- Authority
- ZA
- South Africa
- Prior art keywords
- neodymium
- lanthanide
- phosphonate
- compound
- ethylhexyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 27
- 238000012662 bulk polymerization Methods 0.000 title description 9
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 77
- 150000002602 lanthanoids Chemical class 0.000 claims description 71
- 150000002601 lanthanoid compounds Chemical class 0.000 claims description 48
- 239000000178 monomer Substances 0.000 claims description 43
- -1 lanthanide organophosphonates Chemical class 0.000 claims description 33
- 239000002168 alkylating agent Substances 0.000 claims description 32
- 229940100198 alkylating agent Drugs 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 32
- 239000002904 solvent Substances 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 28
- 238000006116 polymerization reaction Methods 0.000 claims description 26
- 239000003054 catalyst Substances 0.000 claims description 24
- 125000000962 organic group Chemical group 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
- 239000002841 Lewis acid Substances 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 17
- 150000001993 dienes Chemical class 0.000 claims description 17
- 150000007517 lewis acids Chemical class 0.000 claims description 17
- 229910052779 Neodymium Inorganic materials 0.000 claims description 14
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 claims description 11
- 230000003647 oxidation Effects 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 230000000379 polymerizing effect Effects 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 150000001805 chlorine compounds Chemical class 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 3
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- MLCBESZKRKSVFX-UHFFFAOYSA-K 2-ethylhexyl octan-2-yl phosphate neodymium(3+) Chemical compound [Nd+3].CCCCCCC(C)OP([O-])(=O)OCC(CC)CCCC.CCCCCCC(C)OP([O-])(=O)OCC(CC)CCCC.CCCCCCC(C)OP([O-])(=O)OCC(CC)CCCC MLCBESZKRKSVFX-UHFFFAOYSA-K 0.000 claims description 2
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- HMAYLOLHXUPPCA-UHFFFAOYSA-K [Nd+3].[O-]P(=O)Oc1ccccc1.[O-]P(=O)Oc1ccccc1.[O-]P(=O)Oc1ccccc1 Chemical compound [Nd+3].[O-]P(=O)Oc1ccccc1.[O-]P(=O)Oc1ccccc1.[O-]P(=O)Oc1ccccc1 HMAYLOLHXUPPCA-UHFFFAOYSA-K 0.000 claims description 2
- OCLQKMUNLOFINX-UHFFFAOYSA-K [Nd+3].[O-]P(=O)c1ccccc1.[O-]P(=O)c1ccccc1.[O-]P(=O)c1ccccc1 Chemical compound [Nd+3].[O-]P(=O)c1ccccc1.[O-]P(=O)c1ccccc1.[O-]P(=O)c1ccccc1 OCLQKMUNLOFINX-UHFFFAOYSA-K 0.000 claims description 2
- ATQXJRZEZJQPIK-UHFFFAOYSA-K bis(2-ethylhexyl) phosphate;neodymium(3+) Chemical compound [Nd+3].CCCCC(CC)COP([O-])(=O)OCC(CC)CCCC.CCCCC(CC)COP([O-])(=O)OCC(CC)CCCC.CCCCC(CC)COP([O-])(=O)OCC(CC)CCCC ATQXJRZEZJQPIK-UHFFFAOYSA-K 0.000 claims description 2
- JVUAGBYDIROHRJ-UHFFFAOYSA-K bis(2-ethylhexyl)phosphinate;neodymium(3+) Chemical compound [Nd+3].CCCCC(CC)CP([O-])(=O)CC(CC)CCCC.CCCCC(CC)CP([O-])(=O)CC(CC)CCCC.CCCCC(CC)CP([O-])(=O)CC(CC)CCCC JVUAGBYDIROHRJ-UHFFFAOYSA-K 0.000 claims description 2
- JDRFLZCXGCAYAP-UHFFFAOYSA-K bis(4-nonylphenyl) phosphate;neodymium(3+) Chemical compound [Nd+3].C1=CC(CCCCCCCCC)=CC=C1OP([O-])(=O)OC1=CC=C(CCCCCCCCC)C=C1.C1=CC(CCCCCCCCC)=CC=C1OP([O-])(=O)OC1=CC=C(CCCCCCCCC)C=C1.C1=CC(CCCCCCCCC)=CC=C1OP([O-])(=O)OC1=CC=C(CCCCCCCCC)C=C1 JDRFLZCXGCAYAP-UHFFFAOYSA-K 0.000 claims description 2
- WCDXURCGEDAEPN-UHFFFAOYSA-K bis(4-nonylphenyl)phosphinate;neodymium(3+) Chemical compound [Nd+3].C1=CC(CCCCCCCCC)=CC=C1P([O-])(=O)C1=CC=C(CCCCCCCCC)C=C1.C1=CC(CCCCCCCCC)=CC=C1P([O-])(=O)C1=CC=C(CCCCCCCCC)C=C1.C1=CC(CCCCCCCCC)=CC=C1P([O-])(=O)C1=CC=C(CCCCCCCCC)C=C1 WCDXURCGEDAEPN-UHFFFAOYSA-K 0.000 claims description 2
- ILGRJWRWHVWPIO-UHFFFAOYSA-K butyl 2-ethylhexyl phosphate neodymium(3+) Chemical compound [Nd+3].CCCCOP([O-])(=O)OCC(CC)CCCC.CCCCOP([O-])(=O)OCC(CC)CCCC.CCCCOP([O-])(=O)OCC(CC)CCCC ILGRJWRWHVWPIO-UHFFFAOYSA-K 0.000 claims description 2
- VHMIGTCFDWJUOY-UHFFFAOYSA-K butyl(2-ethylhexyl)phosphinate;neodymium(3+) Chemical compound [Nd+3].CCCCC(CC)CP([O-])(=O)CCCC.CCCCC(CC)CP([O-])(=O)CCCC.CCCCC(CC)CP([O-])(=O)CCCC VHMIGTCFDWJUOY-UHFFFAOYSA-K 0.000 claims description 2
- 239000013066 combination product Substances 0.000 claims description 2
- ZTVNMDOSBVIJFG-UHFFFAOYSA-K di(octan-2-yl)phosphinate;neodymium(3+) Chemical compound [Nd+3].CCCCCCC(C)P([O-])(=O)C(C)CCCCCC.CCCCCCC(C)P([O-])(=O)C(C)CCCCCC.CCCCCCC(C)P([O-])(=O)C(C)CCCCCC ZTVNMDOSBVIJFG-UHFFFAOYSA-K 0.000 claims description 2
- XYBPXKSKJGTKJB-UHFFFAOYSA-K dibutylphosphinate;neodymium(3+) Chemical compound [Nd+3].CCCCP([O-])(=O)CCCC.CCCCP([O-])(=O)CCCC.CCCCP([O-])(=O)CCCC XYBPXKSKJGTKJB-UHFFFAOYSA-K 0.000 claims description 2
- KQSNBEOLWQQQBT-UHFFFAOYSA-K didecylphosphinate;neodymium(3+) Chemical compound [Nd+3].CCCCCCCCCCP([O-])(=O)CCCCCCCCCC.CCCCCCCCCCP([O-])(=O)CCCCCCCCCC.CCCCCCCCCCP([O-])(=O)CCCCCCCCCC KQSNBEOLWQQQBT-UHFFFAOYSA-K 0.000 claims description 2
- BRJZEGHWEPTWAX-UHFFFAOYSA-K didodecylphosphinate;neodymium(3+) Chemical compound [Nd+3].CCCCCCCCCCCCP([O-])(=O)CCCCCCCCCCCC.CCCCCCCCCCCCP([O-])(=O)CCCCCCCCCCCC.CCCCCCCCCCCCP([O-])(=O)CCCCCCCCCCCC BRJZEGHWEPTWAX-UHFFFAOYSA-K 0.000 claims description 2
- JTGUKNQMNXAFIS-UHFFFAOYSA-K diheptylphosphinate;neodymium(3+) Chemical compound [Nd+3].CCCCCCCP([O-])(=O)CCCCCCC.CCCCCCCP([O-])(=O)CCCCCCC.CCCCCCCP([O-])(=O)CCCCCCC JTGUKNQMNXAFIS-UHFFFAOYSA-K 0.000 claims description 2
- AXEOTJPPNKRJOQ-UHFFFAOYSA-K dihexyl phosphate;neodymium(3+) Chemical compound [Nd+3].CCCCCCOP([O-])(=O)OCCCCCC.CCCCCCOP([O-])(=O)OCCCCCC.CCCCCCOP([O-])(=O)OCCCCCC AXEOTJPPNKRJOQ-UHFFFAOYSA-K 0.000 claims description 2
- XHFZHPQZVCWVBA-UHFFFAOYSA-K dihexylphosphinate;neodymium(3+) Chemical compound [Nd+3].CCCCCCP([O-])(=O)CCCCCC.CCCCCCP([O-])(=O)CCCCCC.CCCCCCP([O-])(=O)CCCCCC XHFZHPQZVCWVBA-UHFFFAOYSA-K 0.000 claims description 2
- DEYSFYUFFGZQQG-UHFFFAOYSA-K dioctadecylphosphinate;neodymium(3+) Chemical compound [Nd+3].CCCCCCCCCCCCCCCCCCP([O-])(=O)CCCCCCCCCCCCCCCCCC.CCCCCCCCCCCCCCCCCCP([O-])(=O)CCCCCCCCCCCCCCCCCC.CCCCCCCCCCCCCCCCCCP([O-])(=O)CCCCCCCCCCCCCCCCCC DEYSFYUFFGZQQG-UHFFFAOYSA-K 0.000 claims description 2
- JAGXRFFDUAYIAG-UHFFFAOYSA-K dioctan-2-yl phosphate;neodymium(3+) Chemical compound [Nd+3].CCCCCCC(C)OP([O-])(=O)OC(C)CCCCCC.CCCCCCC(C)OP([O-])(=O)OC(C)CCCCCC.CCCCCCC(C)OP([O-])(=O)OC(C)CCCCCC JAGXRFFDUAYIAG-UHFFFAOYSA-K 0.000 claims description 2
- UZSAHKACJKVKEK-UHFFFAOYSA-K dioctylphosphinate;neodymium(3+) Chemical compound [Nd+3].CCCCCCCCP([O-])(=O)CCCCCCCC.CCCCCCCCP([O-])(=O)CCCCCCCC.CCCCCCCCP([O-])(=O)CCCCCCCC UZSAHKACJKVKEK-UHFFFAOYSA-K 0.000 claims description 2
- CMISOYBKHBNISI-UHFFFAOYSA-K dipentylphosphinate;neodymium(3+) Chemical compound [Nd+3].CCCCCP([O-])(=O)CCCCC.CCCCCP([O-])(=O)CCCCC.CCCCCP([O-])(=O)CCCCC CMISOYBKHBNISI-UHFFFAOYSA-K 0.000 claims description 2
- BUHQQXGTFKPOJT-UHFFFAOYSA-K diphenyl phosphate;neodymium(3+) Chemical compound [Nd+3].C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1.C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1.C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 BUHQQXGTFKPOJT-UHFFFAOYSA-K 0.000 claims description 2
- QJXQMMHNTBZSOF-UHFFFAOYSA-K diphenylphosphinate;neodymium(3+) Chemical compound [Nd+3].C=1C=CC=CC=1P(=O)([O-])C1=CC=CC=C1.C=1C=CC=CC=1P(=O)([O-])C1=CC=CC=C1.C=1C=CC=CC=1P(=O)([O-])C1=CC=CC=C1 QJXQMMHNTBZSOF-UHFFFAOYSA-K 0.000 claims description 2
- 125000001117 oleyl 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])/C([H])=C([H])\C([H])([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 claims description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 2
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- YFMDSORVVIWIHS-UHFFFAOYSA-K [Nd+3].CCCCC(CC)CP([O-])=O.CCCCC(CC)CP([O-])=O.CCCCC(CC)CP([O-])=O Chemical compound [Nd+3].CCCCC(CC)CP([O-])=O.CCCCC(CC)CP([O-])=O.CCCCC(CC)CP([O-])=O YFMDSORVVIWIHS-UHFFFAOYSA-K 0.000 claims 1
- YSULVSCKDWCVQT-UHFFFAOYSA-K [Nd+3].CCCCCCC(C)OP([O-])(=O)C(C)CCCCCC.CCCCCCC(C)OP([O-])(=O)C(C)CCCCCC.CCCCCCC(C)OP([O-])(=O)C(C)CCCCCC Chemical compound [Nd+3].CCCCCCC(C)OP([O-])(=O)C(C)CCCCCC.CCCCCCC(C)OP([O-])(=O)C(C)CCCCCC.CCCCCCC(C)OP([O-])(=O)C(C)CCCCCC YSULVSCKDWCVQT-UHFFFAOYSA-K 0.000 claims 1
- UOKRBSXOBUKDGE-UHFFFAOYSA-N butylphosphonic acid Chemical compound CCCCP(O)(O)=O UOKRBSXOBUKDGE-UHFFFAOYSA-N 0.000 claims 1
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- VMIKHUFFDFLOJC-UHFFFAOYSA-M 2-methylpropyl(phenyl)alumanylium;chloride Chemical compound [Cl-].CC(C)C[Al+]C1=CC=CC=C1 VMIKHUFFDFLOJC-UHFFFAOYSA-M 0.000 description 1
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- GNOMLLKHNCKJRX-UHFFFAOYSA-N 2-phenylethylalumane Chemical compound C1(=CC=CC=C1)CC[AlH2] GNOMLLKHNCKJRX-UHFFFAOYSA-N 0.000 description 1
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- 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
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- OYRHKHOWCLRGCQ-UHFFFAOYSA-M butyl-(4-methylphenyl)alumanylium;chloride Chemical compound [Cl-].CCCC[Al+]C1=CC=C(C)C=C1 OYRHKHOWCLRGCQ-UHFFFAOYSA-M 0.000 description 1
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- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- IKNAJTLCCWPIQD-UHFFFAOYSA-K cerium(3+);lanthanum(3+);neodymium(3+);oxygen(2-);phosphate Chemical compound [O-2].[La+3].[Ce+3].[Nd+3].[O-]P([O-])([O-])=O IKNAJTLCCWPIQD-UHFFFAOYSA-K 0.000 description 1
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- LKRBKNPREDAJJQ-UHFFFAOYSA-M chloro-di(propan-2-yl)alumane Chemical compound [Cl-].CC(C)[Al+]C(C)C LKRBKNPREDAJJQ-UHFFFAOYSA-M 0.000 description 1
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- 125000005724 cycloalkenylene group Chemical group 0.000 description 1
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- RQXXJDTUITUSMU-UHFFFAOYSA-M dibenzyl(chloro)alumane Chemical compound [Cl-].C=1C=CC=CC=1C[Al+]CC1=CC=CC=C1 RQXXJDTUITUSMU-UHFFFAOYSA-M 0.000 description 1
- OTACYDLCOLOKPA-UHFFFAOYSA-N dibenzyl(ethyl)alumane Chemical compound C=1C=CC=CC=1C[Al](CC)CC1=CC=CC=C1 OTACYDLCOLOKPA-UHFFFAOYSA-N 0.000 description 1
- DODCHQVKECHKRP-UHFFFAOYSA-N dibenzylalumane Chemical compound C(C1=CC=CC=C1)[AlH]CC1=CC=CC=C1 DODCHQVKECHKRP-UHFFFAOYSA-N 0.000 description 1
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 1
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- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
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- 239000004615 ingredient Substances 0.000 description 1
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- XBKBZMOLSULOEA-UHFFFAOYSA-L methylaluminum(2+);dibromide Chemical compound C[Al](Br)Br XBKBZMOLSULOEA-UHFFFAOYSA-L 0.000 description 1
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- 239000003607 modifier Substances 0.000 description 1
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- KMKBWZXSKDYZDZ-UHFFFAOYSA-M octyl(phenyl)alumanylium;chloride Chemical compound [Cl-].CCCCCCCC[Al+]C1=CC=CC=C1 KMKBWZXSKDYZDZ-UHFFFAOYSA-M 0.000 description 1
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- CUIJJJLOSZSJRO-UHFFFAOYSA-M phenyl(propan-2-yl)alumanylium;chloride Chemical compound [Cl-].CC(C)[Al+]C1=CC=CC=C1 CUIJJJLOSZSJRO-UHFFFAOYSA-M 0.000 description 1
- ZKGDHJAHOGRQEP-UHFFFAOYSA-N phenyl(propyl)alumane Chemical compound C1(=CC=CC=C1)[AlH]CCC ZKGDHJAHOGRQEP-UHFFFAOYSA-N 0.000 description 1
- AAQNAPUTWYBWOV-UHFFFAOYSA-M phenyl(propyl)alumanylium;chloride Chemical compound [Cl-].CCC[Al+]C1=CC=CC=C1 AAQNAPUTWYBWOV-UHFFFAOYSA-M 0.000 description 1
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- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
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- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
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- OBRKWFIGZSMARO-UHFFFAOYSA-N propylalumane Chemical compound [AlH2]CCC OBRKWFIGZSMARO-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
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- 150000003624 transition metals Chemical class 0.000 description 1
- MCWWHQMTJNSXPX-UHFFFAOYSA-N tribenzylalumane Chemical compound C=1C=CC=CC=1C[Al](CC=1C=CC=CC=1)CC1=CC=CC=C1 MCWWHQMTJNSXPX-UHFFFAOYSA-N 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
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- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-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
- 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
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- JQPMDTQDAXRDGS-UHFFFAOYSA-N triphenylalumane Chemical compound C1=CC=CC=C1[Al](C=1C=CC=CC=1)C1=CC=CC=C1 JQPMDTQDAXRDGS-UHFFFAOYSA-N 0.000 description 1
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- QDHQENQYSFSSQA-UHFFFAOYSA-N tris(1-methylcyclopentyl)alumane Chemical compound C1CCCC1(C)[Al](C1(C)CCCC1)C1(C)CCCC1 QDHQENQYSFSSQA-UHFFFAOYSA-N 0.000 description 1
- MYWRONRUDLXRGX-UHFFFAOYSA-N tris(2,2-dimethylpropyl)alumane Chemical compound CC(C)(C)C[Al](CC(C)(C)C)CC(C)(C)C MYWRONRUDLXRGX-UHFFFAOYSA-N 0.000 description 1
- ZHRAFNQICZNWIK-UHFFFAOYSA-N tris(2,6-dimethylphenyl)alumane Chemical compound CC1=CC=CC(C)=C1[Al](C=1C(=CC=CC=1C)C)C1=C(C)C=CC=C1C ZHRAFNQICZNWIK-UHFFFAOYSA-N 0.000 description 1
- FHAOCGKAMRAFMM-UHFFFAOYSA-N tris(2-ethylhexyl)alumane Chemical compound CCCCC(CC)C[Al](CC(CC)CCCC)CC(CC)CCCC FHAOCGKAMRAFMM-UHFFFAOYSA-N 0.000 description 1
- WSITXTIRYQMZHM-UHFFFAOYSA-N tris(4-methylphenyl)alumane Chemical compound C1=CC(C)=CC=C1[Al](C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WSITXTIRYQMZHM-UHFFFAOYSA-N 0.000 description 1
- RTAKQLTYPVIOBZ-UHFFFAOYSA-N tritert-butylalumane Chemical compound CC(C)(C)[Al](C(C)(C)C)C(C)(C)C RTAKQLTYPVIOBZ-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000003911 water pollution Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/02—Polymerisation in bulk
-
- 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
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
-
- 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
- C08F4/06—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen
-
- 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
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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)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Polymerization Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1785507P | 2007-12-31 | 2007-12-31 |
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| ZA200900083B true ZA200900083B (en) | 2010-03-31 |
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| ZA200900083A ZA200900083B (en) | 2007-12-31 | 2009-01-05 | Bulk polymerization process for producing polydienes |
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| US (1) | US8188201B2 (de) |
| EP (1) | EP2075266B1 (de) |
| JP (3) | JP5345835B2 (de) |
| KR (2) | KR101628356B1 (de) |
| CN (1) | CN101525396B (de) |
| BR (1) | BRPI0812683B1 (de) |
| ES (1) | ES2457848T3 (de) |
| RU (1) | RU2515980C2 (de) |
| ZA (1) | ZA200900083B (de) |
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| US8324329B2 (en) * | 2007-08-07 | 2012-12-04 | Bridgestone Corporation | Process for producing functionalized polymers |
| US8314189B2 (en) | 2007-10-12 | 2012-11-20 | Bridgestone Corporation | Polymers functionalized with heterocyclic nitrile compounds |
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| US8268933B2 (en) * | 2007-12-31 | 2012-09-18 | Bridgestone Corporation | Polymers functionalized with polyimine compounds |
| US7906592B2 (en) * | 2008-07-03 | 2011-03-15 | Bridgestone Corporation | Polymers functionalized with imide compounds containing a protected amino group |
| US8188195B2 (en) | 2008-12-31 | 2012-05-29 | Bridgestone Corporation | Polymers functionalized with nitroso compounds |
| WO2010085631A2 (en) | 2009-01-23 | 2010-07-29 | Bridgestone Corporation | Polymers functionalized with polycyano compounds |
| EP2382240B1 (de) | 2009-01-23 | 2014-04-16 | Bridgestone Corporation | Durch nitrilverbindungen mit einer geschützten aminogruppe funktionalisierte polymere |
| US8338544B2 (en) | 2009-12-21 | 2012-12-25 | Bridgestone Corporation | Polymers functionalized with polyoxime compounds and methods for their manufacture |
| RU2456292C2 (ru) * | 2010-08-12 | 2012-07-20 | Федеральное государственное бюджетное учреждение науки Ордена Трудового Красного Знамени Институт нефтехимического синтеза им. А.В. Топчиева Российской академии наук (ИНХС РАН) | Арилфосфаты неодима и катализатор полимеризации сопряженных диенов с их использованием |
| CN101914183B (zh) * | 2010-09-04 | 2012-08-15 | 大连理工大学 | 稀土催化体系苯乙烯/异戊二烯/丁二烯三元无规共聚物及其制备方法 |
| WO2012040026A1 (en) | 2010-09-23 | 2012-03-29 | Bridgestone Corporation | Process for producing polydienes |
| KR101279977B1 (ko) * | 2010-10-18 | 2013-07-05 | 제일모직주식회사 | 공액 디엔으로부터 고무변성 방향족 비닐중합체를 연속적으로 제조하는 방법 |
| US8748531B2 (en) | 2010-12-10 | 2014-06-10 | Bridgestone Corporation | Polymers functionalized with oxime compounds containing an acyl group |
| US8962766B2 (en) | 2011-09-15 | 2015-02-24 | Bridgestone Corporation | Polymers functionalized with polyhydrazone compounds |
| RU2605552C2 (ru) * | 2011-11-17 | 2016-12-20 | Бриджстоун Корпорейшн | Способ получения полидиенов |
| JP6209582B2 (ja) * | 2012-03-14 | 2017-10-04 | 株式会社ブリヂストン | ポリジエン製造プロセス |
| JP6318142B2 (ja) * | 2012-03-30 | 2018-04-25 | 株式会社ブリヂストン | ホスフィド開始剤を用いる機能性ポリマーの調製 |
| FR2998895B1 (fr) * | 2012-12-04 | 2015-07-31 | Michelin & Cie | Nouveau systeme catalytique multi-composants, son procede de preparation et procede de polymerisation de l'isoprene le mettant en œuvre |
| CN105814132A (zh) * | 2013-12-03 | 2016-07-27 | 株式会社普利司通 | 用于制备顺式-1，4-聚丁二烯和间同立构1，2-聚丁二烯的共混物的方法 |
| US20170335032A1 (en) * | 2014-11-17 | 2017-11-23 | Bridgestone Corporation | Bulk polymerization of polyisoprene with preformed catalyst |
| EP4047049A1 (de) | 2014-12-23 | 2022-08-24 | Bridgestone Americas Tire Operations, LLC | Ölhaltigen kautschukzusammensetzungen und zugehörige verfahren |
| CN108219046A (zh) * | 2016-12-15 | 2018-06-29 | 中国石油天然气股份有限公司 | 一种稀土催化剂及其制备方法和应用 |
| RU2660414C1 (ru) * | 2017-05-29 | 2018-07-06 | Федеральное государственное унитарное предприятие "Ордена Ленина и ордена Трудового Красного Знамени научно-исследовательский институт синтетического каучука имени академика С.В. Лебедева" (ФГУП "НИИСК") | Способ получения катализатора полимеризации изопрена |
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| CN116023533A (zh) * | 2021-10-25 | 2023-04-28 | 中国石油化工股份有限公司 | 膦酸酯钕溶液及其制备方法和应用 |
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- 2008-12-26 JP JP2008334062A patent/JP5345835B2/ja active Active
- 2008-12-26 RU RU2008151974/04A patent/RU2515980C2/ru active
- 2008-12-29 BR BRPI0812683-6A patent/BRPI0812683B1/pt active IP Right Grant
- 2008-12-30 EP EP08254179.8A patent/EP2075266B1/de active Active
- 2008-12-30 ES ES08254179.8T patent/ES2457848T3/es active Active
- 2008-12-30 KR KR1020080137306A patent/KR101628356B1/ko active IP Right Grant
- 2008-12-30 US US12/345,901 patent/US8188201B2/en active Active
- 2008-12-31 CN CN200810192997.XA patent/CN101525396B/zh active Active
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2009
- 2009-01-05 ZA ZA200900083A patent/ZA200900083B/en unknown
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2013
- 2013-06-12 JP JP2013123902A patent/JP2013237843A/ja active Pending
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2015
- 2015-07-28 JP JP2015148689A patent/JP2016028141A/ja active Pending
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2016
- 2016-01-18 KR KR1020160005865A patent/KR101692793B1/ko active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| JP2009161757A (ja) | 2009-07-23 |
| JP2013237843A (ja) | 2013-11-28 |
| EP2075266A3 (de) | 2009-08-12 |
| KR20160011691A (ko) | 2016-02-01 |
| CN101525396B (zh) | 2015-07-01 |
| RU2008151974A (ru) | 2010-07-10 |
| JP5345835B2 (ja) | 2013-11-20 |
| KR101692793B1 (ko) | 2017-01-04 |
| CN101525396A (zh) | 2009-09-09 |
| US20100004413A1 (en) | 2010-01-07 |
| EP2075266A2 (de) | 2009-07-01 |
| BRPI0812683A2 (pt) | 2010-08-10 |
| BRPI0812683A8 (pt) | 2019-01-08 |
| RU2515980C2 (ru) | 2014-05-20 |
| JP2016028141A (ja) | 2016-02-25 |
| BRPI0812683B1 (pt) | 2019-05-28 |
| KR20090073989A (ko) | 2009-07-03 |
| ES2457848T3 (es) | 2014-04-29 |
| KR101628356B1 (ko) | 2016-06-08 |
| EP2075266B1 (de) | 2014-01-15 |
| US8188201B2 (en) | 2012-05-29 |
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