JP2022519243A - 低減されたコールドフローを有するポリジエンの製造方法 - Google Patents
低減されたコールドフローを有するポリジエンの製造方法 Download PDFInfo
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- JP2022519243A JP2022519243A JP2021544458A JP2021544458A JP2022519243A JP 2022519243 A JP2022519243 A JP 2022519243A JP 2021544458 A JP2021544458 A JP 2021544458A JP 2021544458 A JP2021544458 A JP 2021544458A JP 2022519243 A JP2022519243 A JP 2022519243A
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- Prior art keywords
- benzenetricarboxylate
- compound
- polymer
- benzene tricarboxylate
- tri
- 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.)
- Granted
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- 238000000034 method Methods 0.000 title claims description 41
- 229920000642 polymer Polymers 0.000 claims abstract description 102
- -1 trimellitic acid ester compound Chemical class 0.000 claims abstract description 93
- 239000000178 monomer Substances 0.000 claims abstract description 67
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- 229910052747 lanthanoid Inorganic materials 0.000 claims abstract description 53
- 150000002602 lanthanoids Chemical class 0.000 claims abstract description 44
- 239000011230 binding agent Substances 0.000 claims abstract description 41
- 229910052751 metal Inorganic materials 0.000 claims abstract description 34
- 239000002184 metal Substances 0.000 claims abstract description 32
- 150000001993 dienes Chemical class 0.000 claims abstract description 26
- ARCGXLSVLAOJQL-UHFFFAOYSA-N anhydrous trimellitic acid Natural products OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 claims abstract description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 84
- 239000000203 mixture Substances 0.000 claims description 71
- 238000006243 chemical reaction Methods 0.000 claims description 50
- 230000008569 process Effects 0.000 claims description 28
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 19
- 239000005062 Polybutadiene Substances 0.000 claims description 18
- 229920002857 polybutadiene Polymers 0.000 claims description 18
- KRADHMIOFJQKEZ-UHFFFAOYSA-N Tri-2-ethylhexyl trimellitate Chemical compound CCCCC(CC)COC(=O)C1=CC=C(C(=O)OCC(CC)CCCC)C(C(=O)OCC(CC)CCCC)=C1 KRADHMIOFJQKEZ-UHFFFAOYSA-N 0.000 claims description 16
- 239000002168 alkylating agent Substances 0.000 claims description 14
- 229940100198 alkylating agent Drugs 0.000 claims description 14
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 11
- 239000004568 cement Substances 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000007791 liquid phase Substances 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 239000011414 polymer cement Substances 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 6
- MJHNUUNSCNRGJE-UHFFFAOYSA-N trimethyl benzene-1,2,4-tricarboxylate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C(C(=O)OC)=C1 MJHNUUNSCNRGJE-UHFFFAOYSA-N 0.000 claims description 6
- YPDXSCXISVYHOB-UHFFFAOYSA-N tris(7-methyloctyl) benzene-1,2,4-tricarboxylate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCC(C)C)C(C(=O)OCCCCCCC(C)C)=C1 YPDXSCXISVYHOB-UHFFFAOYSA-N 0.000 claims description 6
- 241001441571 Hiodontidae Species 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 5
- BOEDOBCDGBKPRR-UHFFFAOYSA-N tris(2-ethylhexyl) benzene-1,2,3-tricarboxylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC(C(=O)OCC(CC)CCCC)=C1C(=O)OCC(CC)CCCC BOEDOBCDGBKPRR-UHFFFAOYSA-N 0.000 claims description 4
- HDYJUDNYXOWDOP-UHFFFAOYSA-N tris(2-ethylhexyl) benzene-1,3,5-tricarboxylate Chemical compound CCCCC(CC)COC(=O)C1=CC(C(=O)OCC(CC)CCCC)=CC(C(=O)OCC(CC)CCCC)=C1 HDYJUDNYXOWDOP-UHFFFAOYSA-N 0.000 claims description 4
- SFYUOIZCGBZMSY-UHFFFAOYSA-N 2,4,6-tridodecylbenzene-1,3,5-tricarboxylic acid Chemical compound CCCCCCCCCCCCc1c(C(O)=O)c(CCCCCCCCCCCC)c(C(O)=O)c(CCCCCCCCCCCC)c1C(O)=O SFYUOIZCGBZMSY-UHFFFAOYSA-N 0.000 claims description 3
- QZERFEKFKAOCNQ-UHFFFAOYSA-N 3-tridecoxycarbonylphthalic acid Chemical compound CCCCCCCCCCCCCOC(=O)C1=CC=CC(=C1C(=O)O)C(=O)O QZERFEKFKAOCNQ-UHFFFAOYSA-N 0.000 claims description 3
- CAAJFRTTZWFVFF-UHFFFAOYSA-N 4-tridecoxycarbonylbenzene-1,3-dicarboxylic acid Chemical compound CCCCCCCCCCCCCOC(=O)C1=CC=C(C(O)=O)C=C1C(O)=O CAAJFRTTZWFVFF-UHFFFAOYSA-N 0.000 claims description 3
- HWJAFQXHBANUCW-UHFFFAOYSA-N 5-tridecoxycarbonylbenzene-1,3-dicarboxylic acid Chemical compound CCCCCCCCCCCCCOC(=O)C1=CC(=CC(=C1)C(=O)O)C(=O)O HWJAFQXHBANUCW-UHFFFAOYSA-N 0.000 claims description 3
- ZLGHBJRBMXMXIK-UHFFFAOYSA-N C(C1=CC(C(=O)OCCCCCCC)=CC(C(=O)OCCCCCCC)=C1)(=O)OCCCCCCC Chemical compound C(C1=CC(C(=O)OCCCCCCC)=CC(C(=O)OCCCCCCC)=C1)(=O)OCCCCCCC ZLGHBJRBMXMXIK-UHFFFAOYSA-N 0.000 claims description 3
- IHRQEWBOSXXVRQ-UHFFFAOYSA-N C1(=C(C(=CC=C1)C(=O)OCCCCCC)C(=O)OCCCCCC)C(=O)OCCCCCC Chemical compound C1(=C(C(=CC=C1)C(=O)OCCCCCC)C(=O)OCCCCCC)C(=O)OCCCCCC IHRQEWBOSXXVRQ-UHFFFAOYSA-N 0.000 claims description 3
- QBMDTGWWQCZIJY-UHFFFAOYSA-N CCCCCCCCCCCCC1=C(C(=C(C(=C1CCCCCCCCCCCC)C(=O)O)C(=O)O)C(=O)O)CCCCCCCCCCCC Chemical compound CCCCCCCCCCCCC1=C(C(=C(C(=C1CCCCCCCCCCCC)C(=O)O)C(=O)O)C(=O)O)CCCCCCCCCCCC QBMDTGWWQCZIJY-UHFFFAOYSA-N 0.000 claims description 3
- 150000002798 neodymium compounds Chemical class 0.000 claims description 3
- JYGDRAJZDZUIRE-UHFFFAOYSA-N tricyclohexyl benzene-1,2,3-tricarboxylate Chemical compound C=1C=CC(C(=O)OC2CCCCC2)=C(C(=O)OC2CCCCC2)C=1C(=O)OC1CCCCC1 JYGDRAJZDZUIRE-UHFFFAOYSA-N 0.000 claims description 3
- NGXQRWJDOKUJEN-UHFFFAOYSA-N triethyl benzene-1,2,4-tricarboxylate Chemical compound CCOC(=O)C1=CC=C(C(=O)OCC)C(C(=O)OCC)=C1 NGXQRWJDOKUJEN-UHFFFAOYSA-N 0.000 claims description 3
- KXGOWZRHSOJOLF-UHFFFAOYSA-N triethyl benzene-1,3,5-tricarboxylate Chemical compound CCOC(=O)C1=CC(C(=O)OCC)=CC(C(=O)OCC)=C1 KXGOWZRHSOJOLF-UHFFFAOYSA-N 0.000 claims description 3
- BYCGLMSRDWQIBW-UHFFFAOYSA-N triheptyl benzene-1,2,3-tricarboxylate Chemical compound C1(=C(C(=CC=C1)C(=O)OCCCCCCC)C(=O)OCCCCCCC)C(=O)OCCCCCCC BYCGLMSRDWQIBW-UHFFFAOYSA-N 0.000 claims description 3
- MXHBQKVKHGQWRB-UHFFFAOYSA-N trihexyl benzene-1,2,4-tricarboxylate Chemical compound CCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCC)C(C(=O)OCCCCCC)=C1 MXHBQKVKHGQWRB-UHFFFAOYSA-N 0.000 claims description 3
- TVQDRVUAQNFLIE-UHFFFAOYSA-N trihexyl benzene-1,3,5-tricarboxylate Chemical compound CCCCCCOC(=O)C1=CC(C(=O)OCCCCCC)=CC(C(=O)OCCCCCC)=C1 TVQDRVUAQNFLIE-UHFFFAOYSA-N 0.000 claims description 3
- SBOCVSUCRFVXFE-UHFFFAOYSA-N trimethyl benzene-1,2,3-tricarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1C(=O)OC SBOCVSUCRFVXFE-UHFFFAOYSA-N 0.000 claims description 3
- RGCHNYAILFZUPL-UHFFFAOYSA-N trimethyl benzene-1,3,5-tricarboxylate Chemical compound COC(=O)C1=CC(C(=O)OC)=CC(C(=O)OC)=C1 RGCHNYAILFZUPL-UHFFFAOYSA-N 0.000 claims description 3
- YQMVQCLVLBAKBX-UHFFFAOYSA-N trioctyl benzene-1,3,5-tricarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC(C(=O)OCCCCCCCC)=CC(C(=O)OCCCCCCCC)=C1 YQMVQCLVLBAKBX-UHFFFAOYSA-N 0.000 claims description 3
- HQZJWMPXPADGDC-UHFFFAOYSA-N tripentyl benzene-1,2,3-tricarboxylate Chemical compound C1(=C(C(=CC=C1)C(=O)OCCCCC)C(=O)OCCCCC)C(=O)OCCCCC HQZJWMPXPADGDC-UHFFFAOYSA-N 0.000 claims description 3
- OTYZITQZGUUIFO-UHFFFAOYSA-N tripentyl benzene-1,2,4-tricarboxylate Chemical compound CCCCCOC(=O)C1=CC=C(C(=O)OCCCCC)C(C(=O)OCCCCC)=C1 OTYZITQZGUUIFO-UHFFFAOYSA-N 0.000 claims description 3
- NJMZAISYTPAALV-UHFFFAOYSA-N tripentyl benzene-1,3,5-tricarboxylate Chemical compound C1(=CC(=CC(=C1)C(=O)OCCCCC)C(=O)OCCCCC)C(=O)OCCCCC NJMZAISYTPAALV-UHFFFAOYSA-N 0.000 claims description 3
- QEUYMNVHNSOBRS-UHFFFAOYSA-N tripropyl benzene-1,2,4-tricarboxylate Chemical compound CCCOC(=O)C1=CC=C(C(=O)OCCC)C(C(=O)OCCC)=C1 QEUYMNVHNSOBRS-UHFFFAOYSA-N 0.000 claims description 3
- QOINGJHPNJTQGL-UHFFFAOYSA-N 2,4,6-tripropylbenzene-1,3,5-tricarboxylic acid Chemical compound CCCC1=C(C(O)=O)C(CCC)=C(C(O)=O)C(CCC)=C1C(O)=O QOINGJHPNJTQGL-UHFFFAOYSA-N 0.000 claims description 2
- SIKAUAVBFVKZJH-UHFFFAOYSA-N CCCCCCCCCOC(=O)C1=CC=CC(C(=O)OCCCCCCCCC)=C1C(=O)OCCCCCCCCC Chemical compound CCCCCCCCCOC(=O)C1=CC=CC(C(=O)OCCCCCCCCC)=C1C(=O)OCCCCCCCCC SIKAUAVBFVKZJH-UHFFFAOYSA-N 0.000 claims description 2
- QNXIFJUFSSPJAV-UHFFFAOYSA-N tributyl benzene-1,2,3-tricarboxylate Chemical compound CCCCOC(=O)C1=CC=CC(C(=O)OCCCC)=C1C(=O)OCCCC QNXIFJUFSSPJAV-UHFFFAOYSA-N 0.000 claims description 2
- RJIFVNWOLLIBJV-UHFFFAOYSA-N tributyl benzene-1,2,4-tricarboxylate Chemical compound CCCCOC(=O)C1=CC=C(C(=O)OCCCC)C(C(=O)OCCCC)=C1 RJIFVNWOLLIBJV-UHFFFAOYSA-N 0.000 claims description 2
- VSBZHJQRHZBXRY-UHFFFAOYSA-N triethyl benzene-1,2,3-tricarboxylate Chemical compound CCOC(=O)C1=CC=CC(C(=O)OCC)=C1C(=O)OCC VSBZHJQRHZBXRY-UHFFFAOYSA-N 0.000 claims description 2
- BKBIWOCOMPSUFK-UHFFFAOYSA-N trioctyl benzene-1,2,3-tricarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=CC(C(=O)OCCCCCCCC)=C1C(=O)OCCCCCCCC BKBIWOCOMPSUFK-UHFFFAOYSA-N 0.000 claims description 2
- WUMQFQTUGXZOSD-UHFFFAOYSA-N tripropyl benzene-1,2,3-tricarboxylate Chemical compound CCCOC(=O)C1=CC=CC(C(=O)OCCC)=C1C(=O)OCCC WUMQFQTUGXZOSD-UHFFFAOYSA-N 0.000 claims description 2
- JCNQIHJXXHDJNK-UHFFFAOYSA-N 2,4,6-tricyclohexylbenzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=C(C2CCCCC2)C(C(O)=O)=C(C2CCCCC2)C(C(=O)O)=C1C1CCCCC1 JCNQIHJXXHDJNK-UHFFFAOYSA-N 0.000 claims 1
- 229920002959 polymer blend Polymers 0.000 abstract description 3
- 238000010586 diagram Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 35
- 239000003054 catalyst Substances 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 229910052779 Neodymium Inorganic materials 0.000 description 19
- 229920001971 elastomer Polymers 0.000 description 13
- 239000005060 rubber Substances 0.000 description 13
- 230000003197 catalytic effect Effects 0.000 description 12
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 12
- 229930195733 hydrocarbon Natural products 0.000 description 10
- 238000009739 binding Methods 0.000 description 9
- 238000010791 quenching Methods 0.000 description 8
- 230000000171 quenching effect Effects 0.000 description 8
- 229920013730 reactive polymer Polymers 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 238000012662 bulk polymerization Methods 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 239000002841 Lewis acid Substances 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 150000007517 lewis acids Chemical class 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 229920003193 cis-1,4-polybutadiene polymer Polymers 0.000 description 5
- 239000012967 coordination catalyst Substances 0.000 description 5
- 150000002601 lanthanoid compounds Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 4
- RCJMVGJKROQDCB-UHFFFAOYSA-N 2-methylpenta-1,3-diene Chemical compound CC=CC(C)=C RCJMVGJKROQDCB-UHFFFAOYSA-N 0.000 description 4
- CJSBUWDGPXGFGA-UHFFFAOYSA-N 4-methylpenta-1,3-diene Chemical compound CC(C)=CC=C CJSBUWDGPXGFGA-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- PSCMQHVBLHHWTO-UHFFFAOYSA-K indium(iii) chloride Chemical compound Cl[In](Cl)Cl PSCMQHVBLHHWTO-UHFFFAOYSA-K 0.000 description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- 239000005063 High cis polybutadiene Substances 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 238000012718 coordination polymerization Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229910001510 metal chloride Inorganic materials 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000012991 xanthate Substances 0.000 description 3
- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 description 2
- BOGRNZQRTNVZCZ-AATRIKPKSA-N (3e)-3-methylpenta-1,3-diene Chemical compound C\C=C(/C)C=C BOGRNZQRTNVZCZ-AATRIKPKSA-N 0.000 description 2
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- BOGRNZQRTNVZCZ-UHFFFAOYSA-N 1,2-dimethyl-butadiene Natural products CC=C(C)C=C BOGRNZQRTNVZCZ-UHFFFAOYSA-N 0.000 description 2
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 description 2
- LQIIEHBULBHJKX-UHFFFAOYSA-N 2-methylpropylalumane Chemical compound CC(C)C[AlH2] LQIIEHBULBHJKX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 229910052772 Samarium Inorganic materials 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- HYZXMVILOKSUKA-UHFFFAOYSA-K chloro(dimethyl)alumane;dichloro(methyl)alumane Chemical compound C[Al](C)Cl.C[Al](Cl)Cl HYZXMVILOKSUKA-UHFFFAOYSA-K 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 2
- VTZJFPSWNQFPCQ-UHFFFAOYSA-N dibutylaluminum Chemical compound CCCC[Al]CCCC VTZJFPSWNQFPCQ-UHFFFAOYSA-N 0.000 description 2
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 2
- JGHYBJVUQGTEEB-UHFFFAOYSA-M dimethylalumanylium;chloride Chemical compound C[Al](C)Cl JGHYBJVUQGTEEB-UHFFFAOYSA-M 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 229910001504 inorganic chloride Inorganic materials 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 229910052746 lanthanum Inorganic materials 0.000 description 2
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 2
- 235000011147 magnesium chloride Nutrition 0.000 description 2
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- 239000003350 kerosene Substances 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- IWCVDCOJSPWGRW-UHFFFAOYSA-M magnesium;benzene;chloride Chemical compound [Mg+2].[Cl-].C1=CC=[C-]C=C1 IWCVDCOJSPWGRW-UHFFFAOYSA-M 0.000 description 1
- QUXHCILOWRXCEO-UHFFFAOYSA-M magnesium;butane;chloride Chemical compound [Mg+2].[Cl-].CCC[CH2-] QUXHCILOWRXCEO-UHFFFAOYSA-M 0.000 description 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 description 1
- SCEZYJKGDJPHQO-UHFFFAOYSA-M magnesium;methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC=C1 SCEZYJKGDJPHQO-UHFFFAOYSA-M 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 239000005055 methyl trichlorosilane Substances 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- NRQNMMBQPIGPTB-UHFFFAOYSA-N methylaluminum Chemical compound [CH3].[Al] NRQNMMBQPIGPTB-UHFFFAOYSA-N 0.000 description 1
- XBKBZMOLSULOEA-UHFFFAOYSA-L methylaluminum(2+);dibromide Chemical compound C[Al](Br)Br XBKBZMOLSULOEA-UHFFFAOYSA-L 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910052590 monazite Inorganic materials 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 238000010068 moulding (rubber) Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- AAIPJXDONHAQHJ-UHFFFAOYSA-K neodymium(3+) tricarbamate Chemical compound [Nd+3].NC([O-])=O.NC([O-])=O.NC([O-])=O AAIPJXDONHAQHJ-UHFFFAOYSA-K 0.000 description 1
- SIINVGJQWZKNSJ-UHFFFAOYSA-K neodymium(3+);octadecanoate Chemical compound [Nd+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O SIINVGJQWZKNSJ-UHFFFAOYSA-K 0.000 description 1
- MHJIJZIBANOIDE-UHFFFAOYSA-K neodymium(3+);prop-2-enoate Chemical compound [Nd+3].[O-]C(=O)C=C.[O-]C(=O)C=C.[O-]C(=O)C=C MHJIJZIBANOIDE-UHFFFAOYSA-K 0.000 description 1
- HPCGPGSYNUPEKZ-UHFFFAOYSA-K neodymium(3+);tribenzoate Chemical compound [Nd+3].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 HPCGPGSYNUPEKZ-UHFFFAOYSA-K 0.000 description 1
- AARCLZBTVAUMJK-UHFFFAOYSA-K neodymium(3+);triformate Chemical compound [Nd+3].[O-]C=O.[O-]C=O.[O-]C=O AARCLZBTVAUMJK-UHFFFAOYSA-K 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JXRJZEIFKKYMBS-UHFFFAOYSA-N octyl(phenyl)alumane Chemical compound C1(=CC=CC=C1)[AlH]CCCCCCCC JXRJZEIFKKYMBS-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002899 organoaluminium compounds Chemical class 0.000 description 1
- 150000002901 organomagnesium compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- QDUCABQBSRSYCO-UHFFFAOYSA-N phenyl(propan-2-yl)alumane Chemical compound C1(=CC=CC=C1)[AlH]C(C)C QDUCABQBSRSYCO-UHFFFAOYSA-N 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
- 239000005054 phenyltrichlorosilane Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
- 238000012673 precipitation polymerization Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- VQMWBBYLQSCNPO-UHFFFAOYSA-N promethium atom Chemical compound [Pm] VQMWBBYLQSCNPO-UHFFFAOYSA-N 0.000 description 1
- 230000001902 propagating effect Effects 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000013040 rubber vulcanization Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- LNBXMNQCXXEHFT-UHFFFAOYSA-N selenium tetrachloride Chemical compound Cl[Se](Cl)(Cl)Cl LNBXMNQCXXEHFT-UHFFFAOYSA-N 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 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
- NJPOTNJJCSJJPJ-UHFFFAOYSA-N tributyl benzene-1,3,5-tricarboxylate Chemical compound CCCCOC(=O)C1=CC(C(=O)OCCCC)=CC(C(=O)OCCCC)=C1 NJPOTNJJCSJJPJ-UHFFFAOYSA-N 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- HNKJQEHAZFEDJD-UHFFFAOYSA-N tricyclohexyl benzene-1,2,4-tricarboxylate Chemical compound C=1C=C(C(=O)OC2CCCCC2)C(C(=O)OC2CCCCC2)=CC=1C(=O)OC1CCCCC1 HNKJQEHAZFEDJD-UHFFFAOYSA-N 0.000 description 1
- ZIYNWDQDHKSRCE-UHFFFAOYSA-N tricyclohexylalumane Chemical compound C1CCCCC1[Al](C1CCCCC1)C1CCCCC1 ZIYNWDQDHKSRCE-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- SYKYENWAGZGAFV-UHFFFAOYSA-N triheptyl benzene-1,2,4-tricarboxylate Chemical compound CCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCC)C(C(=O)OCCCCCCC)=C1 SYKYENWAGZGAFV-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
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- ROPPTGKKZZDFJN-UHFFFAOYSA-N trinonyl benzene-1,2,4-tricarboxylate Chemical compound CCCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCCC)C(C(=O)OCCCCCCCCC)=C1 ROPPTGKKZZDFJN-UHFFFAOYSA-N 0.000 description 1
- YAJSFGLBTBIDSV-UHFFFAOYSA-N trinonyl benzene-1,3,5-tricarboxylate Chemical compound CCCCCCCCCOC(=O)C1=CC(C(=O)OCCCCCCCCC)=CC(C(=O)OCCCCCCCCC)=C1 YAJSFGLBTBIDSV-UHFFFAOYSA-N 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- JOJQVUCWSDRWJE-UHFFFAOYSA-N tripentylalumane Chemical compound CCCCC[Al](CCCCC)CCCCC JOJQVUCWSDRWJE-UHFFFAOYSA-N 0.000 description 1
- 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
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-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
- 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
- 239000003039 volatile agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
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- C08F136/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F136/02—Homopolymers 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
- C08F136/04—Homopolymers 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
- C08F136/06—Butadiene
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- 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
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- C08F4/54—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 together with other compounds thereof
- C08F4/545—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 together with other compounds thereof rare earths being present, e.g. triethylaluminium + neodymium octanoate
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- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
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Abstract
Description
式中、R、R’、及びR’’は、独立して、1~20個の炭素を含有するヒドロカルビル基から選択される。式(2)の化合物の例としては、トリメチル1,2,3-ベンゼントリカルボキシレート、トリエチル1,2,3-ベンゼントリカルボキシレート、トリプロピル1,2,3-ベンゼントリカルボキシレート、トリブチル1,2,3-ベンゼントリカルボキシレート、トリペンチル1,2,3-ベンゼントリカルボキシレート、トリヘキシル1,2,3-ベンゼントリカルボキシレート、トリヘプチル1,2,3-ベンゼントリカルボキシレート、トリシクロヘキシル1,2,3-ベンゼントリカルボキシレート、トリオクチル1,2,3-ベンゼントリカルボキシレート、トリ(2-エチルヘキシル)1,2,3-ベンゼントリカルボキシレート、トリノニル1,2,3-ベンゼントリカルボキシレート、トリデシル1,2,3-ベンゼントリカルボキシレート、トリドデシル1,2,3-ベンゼントリカルボキシレート、ブチルジメチル1,2,3-ベンゼントリカルボキシレート、及びブチルジエチル1,2,3-ベンゼントリカルボキシレートが挙げられる。非有機金属トリメリット酸エステル結合剤の他の例は、トリ(2-エチルヘキシル)1,2,3-ベンゼントリカルボキシレートとしても知られているトリ-2-エチルヘキシルヘミメリテート又はトリノニル1,2,3-ベンゼントリカルボキシレートとしても知られているトリイソノニルヘミメリテートである。
式中、R、R’、及びR’’は、独立して、1~20個の炭素を含有するヒドロカルビル基から選択される。式(3)の化合物の例としては、トリメチル1,3,5-ベンゼントリカルボキシレート、トリエチル1,3,5-ベンゼントリカルボキシレート、トリプロピル1,3,5-ベンゼントリカルボキシレート、トリブチル1,3,5-ベンゼントリカルボキシレート、トリペンチル1,3,5-ベンゼントリカルボキシレート、トリヘキシル1,3,5-ベンゼントリカルボキシレート、トリヘプチル1,3,5-ベンゼントリカルボキシレート、トリシクロヘキシル1,3,5-ベンゼントリカルボキシレート、トリオクチル1,3,5-ベンゼントリカルボキシレート、トリ(2-エチルヘキシル)1,3,5-ベンゼントリカルボキシレート、トリノニル1,3,5-ベンゼントリカルボキシレート、トリデシル1,3,5-ベンゼントリカルボキシレート、トリドデシル1,3,5-ベンゼントリカルボキシレート、ブチルジメチル1,3,5-ベンゼントリカルボキシレート、及びブチルジエチル1,3,5-ベンゼントリカルボキシレートが挙げられる。非有機金属トリメリット酸エステル結合剤の他の例は、トリ(2-エチルヘキシル)1,3,5-ベンゼントリカルボキシレートとしても知られているトリ-2-エチルヘキシルトリメシテート又はトリノニル1,3,5-ベンゼントリカルボキシレートとしても知られているトリイソノニルトリメシテートである。
Claims (15)
- ポリジエンを調製するためのプロセスであって、
a.共役ジエンモノマーを液相重合混合物内で60%以上の転化率に重合して、中間体ポリマーを形成する工程であって、前記液相重合混合物が、共役ジエンモノマー、ランタニド含有化合物、及びアルキル化剤を含み、前記中間体ポリマーが、ベースムーニー粘度を含む、形成する工程と、
b.前記中間体ポリマーに、結合剤として非有機金属芳香族トリエステル化合物を約0.02~約0.12phmの量で添加する工程であって、前記非有機金属トリメリット酸エステル化合物の前記添加が、前記中間体ポリマーの前記ベースムーニー粘度を約30~約80%の範囲で増加させる、添加する工程と、を含む、プロセス。 - 工程(a)の前記中間体ポリマーが、ベースコールドフロー値を含み、前記非有機金属芳香族トリエステル化合物の前記添加が、前記中間体ポリマーの前記ベースコールドフロー値を約20~約50%の範囲で増加させる、請求項1に記載のプロセス。
- 前記ランタニド含有化合物が、ネオジム化合物である、請求項1に記載のプロセス。
- 前記非有機金属芳香族トリムエステル化合物が、トリメチル1,2,4-ベンゼントリカルボキシレート、トリエチル1,2,4-ベンゼントリカルボキシレート、トリプロピル1,2,4-ベンゼントリカルボキシレート、トリブチル1,2,4-ベンゼントリカルボキシレート、トリペンチル1,2,4-ベンゼントリカルボキシレート、トリヘキシル1,2,4-ベンゼントリカルボキシレート、トリヘプチル1,2,4-ベンゼントリカルボキシレート、トリシクロヘキシル1,2,4-ベンゼントリカルボキシレート、トリオクチル1,2,4-ベンゼントリカルボキシレート、トリ(2-エチルヘキシル)1,2,4-ベンゼントリカルボキシレート、トリノニル1,2,4-ベンゼントリカルボキシレート、トリデシル1,2,4-ベンゼントリカルボキシレート、トリドデシル1,2,4-ベンゼントリカルボキシレート、ブチルジメチル1,2,4-ベンゼントリカルボキシレート、ブチルジエチル1,2,4-ベンゼントリカルボキシレート、トリ-2-エチルヘキシルトリメリテート及びトリイソノニルトリメリテートからなる群から選択される、請求項4に記載のプロセス。
- 前記非有機金属芳香族トリムエステル化合物が、トリメチル1,2,3-ベンゼントリカルボキシレート、トリエチル1,2,3-ベンゼントリカルボキシレート、トリプロピル1,2,3-ベンゼントリカルボキシレート、トリブチル1,2,3-ベンゼントリカルボキシレート、トリペンチル1,2,3-ベンゼントリカルボキシレート、トリヘキシル1,2,3-ベンゼントリカルボキシレート、トリヘプチル1,2,3-ベンゼントリカルボキシレート、トリシクロヘキシル1,2,3-ベンゼントリカルボキシレート、トリオクチル1,2,3-ベンゼントリカルボキシレート、トリ(2-エチルヘキシル)1,2,3-ベンゼントリカルボキシレート、トリノニル1,2,3-ベンゼントリカルボキシレート、トリデシル1,2,3-ベンゼントリカルボキシレート、トリドデシル1,2,3-ベンゼントリカルボキシレート、ブチルジメチル1,2,3-ベンゼントリカルボキシレート、ブチルジエチル1,2,3-ベンゼントリカルボキシレート、トリ-2-エチルヘキシルヘミメリテート及びトリイソノニルヘミメリテートからなる群から選択される、請求項6に記載のプロセス。
- 前記非有機金属芳香族トリムエステル化合物が、トリメチル1,3,5-ベンゼントリカルボキシレート、トリエチル1,3,5-ベンゼントリカルボキシレート、トリプロピル1,3,5-ベンゼントリカルボキシレート、トリブチル1,3,5-ベンゼントリカルボキシレート、トリペンチル1,3,5-ベンゼントリカルボキシレート、トリヘキシル1,3,5-ベンゼントリカルボキシレート、トリヘプチル1,3,5-ベンゼントリカルボキシレート、トリシクロヘキシル1,3,5-ベンゼントリカルボキシレート、トリオクチル1,3,5-ベンゼントリカルボキシレート、トリ(2-エチルヘキシル)1,3,5-ベンゼントリカルボキシレート、トリノニル1,3,5-ベンゼントリカルボキシレート、トリデシル1,3,5-ベンゼントリカルボキシレート、トリドデシル1,3,5-ベンゼントリカルボキシレート、ブチルジメチル1,3,5-ベンゼントリカルボキシレート、ブチルジエチル1,3,5-ベンゼントリカルボキシレート、トリ-2-エチルヘキシルトリメシテート及びトリイソノニルトリメシテートからなる群から選択される、請求項8に記載のプロセス。
- 前記非有機金属芳香族トリエステル化合物が、前記中間体ポリマーに約0.035~約0.085phmの量で添加され、前記ランタニド含有化合物の量が、共役ジエンモノマー100g当たり約0.001~約2mmolの量で存在する、請求項1に記載のプロセス。
- 請求項1に記載のプロセスで調製されるポリジエンポリマーであって、約35~約45(ML1+4)の範囲のムーニー粘度を有する、ポリジエンポリマー。
- ポリブタジエンを調製するためのプロセスであって、
a.ブタジエンモノマーをランタニド含有化合物及びアルキル化剤の存在下で反応容器内で80%以上の転化率に重合して、中間体ポリマーを形成する工程と、
b.前記中間体ポリマーを第2の反応容器に移動させる工程と、
c.前記第2の反応容器内のポリマーセメントに、結合剤として非有機金属芳香族トリエステル化合物を約0.02~約0.12phmの量で添加して、ポリブタジエンセメントを形成する工程であって、前記ポリブタジエンセメントが、約35~約45(ML1+4)の範囲のムーニー粘度を含む、形成する工程と、を含む、プロセス。 - 前記非有機金属芳香族トリエステル化合物が、トリ-2-エチルヘキシルトリメリテート又はトリイソノニルトリメリテートからなる群から選択されるトリメリット酸エステル化合物である、請求項12に記載のプロセス。
- 前記第2の反応容器に移動した前記中間体ポリマーが、約20~約30(ML1+4)の範囲のムーニー粘度を含む、請求項12に記載のプロセス。
- 前記工程aが、前記反応容器内にハロゲン含有化合物を更に含む、請求項12に記載のプロセス。
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