JP2019522100A - ランタニドベース触媒組成物によって高シス−1,4−ポリジエンを製造するプロセス - Google Patents
ランタニドベース触媒組成物によって高シス−1,4−ポリジエンを製造するプロセス Download PDFInfo
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- JP2019522100A JP2019522100A JP2019504689A JP2019504689A JP2019522100A JP 2019522100 A JP2019522100 A JP 2019522100A JP 2019504689 A JP2019504689 A JP 2019504689A JP 2019504689 A JP2019504689 A JP 2019504689A JP 2019522100 A JP2019522100 A JP 2019522100A
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- Prior art keywords
- silane
- neodymium
- compound
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- tri
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- 239000003054 catalyst Substances 0.000 title claims abstract description 131
- 229910052747 lanthanoid Inorganic materials 0.000 title claims abstract description 52
- 150000002602 lanthanoids Chemical class 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title claims abstract description 47
- 230000008569 process Effects 0.000 title claims abstract description 12
- 239000000203 mixture Substances 0.000 title claims description 82
- 239000000178 monomer Substances 0.000 claims abstract description 100
- 150000001993 dienes Chemical class 0.000 claims abstract description 28
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 166
- 238000006116 polymerization reaction Methods 0.000 claims description 87
- -1 aluminum compound Chemical class 0.000 claims description 85
- 239000003795 chemical substances by application Substances 0.000 claims description 55
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical class 0.000 claims description 34
- 239000002168 alkylating agent Substances 0.000 claims description 29
- 229940100198 alkylating agent Drugs 0.000 claims description 29
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 27
- 229910000077 silane Inorganic materials 0.000 claims description 22
- 229910052782 aluminium Inorganic materials 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 17
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 15
- 125000000962 organic group Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 13
- 150000002601 lanthanoid compounds Chemical class 0.000 claims description 12
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 6
- 150000007942 carboxylates Chemical group 0.000 claims description 5
- 150000004703 alkoxides Chemical group 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- DAIOTEJKUWOIGJ-UHFFFAOYSA-N 2,2-dimethoxyethoxy(ethyl)silane Chemical compound C(C)[SiH2]OCC(OC)OC DAIOTEJKUWOIGJ-UHFFFAOYSA-N 0.000 claims description 2
- ITSKDXURRACCOF-UHFFFAOYSA-N 2,2-dimethoxyethoxy(hexyl)silane Chemical compound C(CCCCC)[SiH2]OCC(OC)OC ITSKDXURRACCOF-UHFFFAOYSA-N 0.000 claims description 2
- KTYPBQYIEGTBNT-UHFFFAOYSA-N 2,2-dimethoxyethoxy(methyl)silane Chemical compound C[SiH2]OCC(OC)OC KTYPBQYIEGTBNT-UHFFFAOYSA-N 0.000 claims description 2
- UOPVAHZRKHBSAZ-UHFFFAOYSA-N 2,2-dimethoxyethoxy(propan-2-yl)silane Chemical compound C(C)(C)[SiH2]OCC(OC)OC UOPVAHZRKHBSAZ-UHFFFAOYSA-N 0.000 claims description 2
- QLCASOSULRITOF-UHFFFAOYSA-N 2,2-dimethoxyethoxy(propyl)silane Chemical compound C(CC)[SiH2]OCC(OC)OC QLCASOSULRITOF-UHFFFAOYSA-N 0.000 claims description 2
- JZGPNMKIIPNQMH-UHFFFAOYSA-N 2,2-dimethylpropyl(triethoxy)silane Chemical compound CCO[Si](CC(C)(C)C)(OCC)OCC JZGPNMKIIPNQMH-UHFFFAOYSA-N 0.000 claims description 2
- WBRUCSICGDSGEV-UHFFFAOYSA-N 2,2-dimethylpropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CC(C)(C)C WBRUCSICGDSGEV-UHFFFAOYSA-N 0.000 claims description 2
- JOHRDHCXAZQKNU-UHFFFAOYSA-N 2,2-dimethylpropyl(triphenoxy)silane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(CC(C)(C)C)OC1=CC=CC=C1 JOHRDHCXAZQKNU-UHFFFAOYSA-N 0.000 claims description 2
- NABUIFHXOUMXRB-UHFFFAOYSA-N 2,2-dimethylpropyl-dimethoxy-phenoxysilane Chemical compound C(C(C)(C)C)[Si](OC1=CC=CC=C1)(OC)OC NABUIFHXOUMXRB-UHFFFAOYSA-N 0.000 claims description 2
- YMJYBUHLJGIAOM-UHFFFAOYSA-N 2,2-diphenoxyethoxy(ethyl)silane Chemical compound C(C)[SiH2]OCC(OC1=CC=CC=C1)OC1=CC=CC=C1 YMJYBUHLJGIAOM-UHFFFAOYSA-N 0.000 claims description 2
- AWENSURFXFRPCR-UHFFFAOYSA-N 2,2-diphenoxyethoxy(methyl)silane Chemical compound C[SiH2]OCC(OC1=CC=CC=C1)OC1=CC=CC=C1 AWENSURFXFRPCR-UHFFFAOYSA-N 0.000 claims description 2
- QGXBFQKGBYTQKH-UHFFFAOYSA-N 2,2-diphenoxyethoxy(phenyl)silane Chemical compound C1(=CC=CC=C1)[SiH2]OCC(OC1=CC=CC=C1)OC1=CC=CC=C1 QGXBFQKGBYTQKH-UHFFFAOYSA-N 0.000 claims description 2
- DAGGOPQICSSNHR-UHFFFAOYSA-N 2,2-diphenylethoxy(ethyl)silane Chemical compound C(C)[SiH2]OCC(C1=CC=CC=C1)C1=CC=CC=C1 DAGGOPQICSSNHR-UHFFFAOYSA-N 0.000 claims description 2
- AQUDJXUZIGQKHD-UHFFFAOYSA-N 2,2-diphenylethoxy(propan-2-yl)silane Chemical compound C(C)(C)[SiH2]OCC(C1=CC=CC=C1)C1=CC=CC=C1 AQUDJXUZIGQKHD-UHFFFAOYSA-N 0.000 claims description 2
- ZNBGSAANFQPPEQ-UHFFFAOYSA-N 2-(1,3-diphenylpropan-2-yloxy)ethoxysilane Chemical compound C(C1=CC=CC=C1)C(OCCO[SiH3])CC1=CC=CC=C1 ZNBGSAANFQPPEQ-UHFFFAOYSA-N 0.000 claims description 2
- PCBUFUDJULPURA-UHFFFAOYSA-N 2-benzhydryloxyethoxysilane Chemical compound C1(=CC=CC=C1)C(OCCO[SiH3])C1=CC=CC=C1 PCBUFUDJULPURA-UHFFFAOYSA-N 0.000 claims description 2
- KVMAQXBSRFDBSI-UHFFFAOYSA-N 2-methoxyethoxy(dimethyl)silane Chemical compound COCCO[SiH](C)C KVMAQXBSRFDBSI-UHFFFAOYSA-N 0.000 claims description 2
- IQVAUSGDJXXPCI-UHFFFAOYSA-N 2-methoxyethoxy(dipentyl)silane Chemical compound C(CCCC)[SiH](OCCOC)CCCCC IQVAUSGDJXXPCI-UHFFFAOYSA-N 0.000 claims description 2
- NTGFGMVYTAPOSF-UHFFFAOYSA-N 2-methoxyethoxy(dipropyl)silane Chemical compound C(CC)[SiH](OCCOC)CCC NTGFGMVYTAPOSF-UHFFFAOYSA-N 0.000 claims description 2
- OUGSKMFDYNNVME-UHFFFAOYSA-N 2-methoxyethoxy-methyl-phenoxysilane Chemical compound C[SiH](OC1=CC=CC=C1)OCCOC OUGSKMFDYNNVME-UHFFFAOYSA-N 0.000 claims description 2
- KRBOVOGLTFZXMC-UHFFFAOYSA-N 2-methoxyethoxy-phenoxy-propylsilane Chemical compound C(CC)[SiH](OC1=CC=CC=C1)OCCOC KRBOVOGLTFZXMC-UHFFFAOYSA-N 0.000 claims description 2
- PEDPZOJOTKHTBP-UHFFFAOYSA-N 2-phenoxyethoxy(diphenyl)silane Chemical compound C1(=CC=CC=C1)[SiH](OCCOC1=CC=CC=C1)C1=CC=CC=C1 PEDPZOJOTKHTBP-UHFFFAOYSA-N 0.000 claims description 2
- VTGNLFOIRAQHTF-UHFFFAOYSA-N C(C(C)(C)C)[SiH2]OCC(OC)OC Chemical compound C(C(C)(C)C)[SiH2]OCC(OC)OC VTGNLFOIRAQHTF-UHFFFAOYSA-N 0.000 claims description 2
- DUTGKIZYZRNIDR-UHFFFAOYSA-N C(C(C)(C)C)[SiH2]OCC(OC1=CC=CC=C1)OC1=CC=CC=C1 Chemical compound C(C(C)(C)C)[SiH2]OCC(OC1=CC=CC=C1)OC1=CC=CC=C1 DUTGKIZYZRNIDR-UHFFFAOYSA-N 0.000 claims description 2
- CBEXFINPRFXISA-UHFFFAOYSA-N C(C(C)(C)C)[SiH](OC1=CC=CC=C1)OCCOC Chemical compound C(C(C)(C)C)[SiH](OC1=CC=CC=C1)OCCOC CBEXFINPRFXISA-UHFFFAOYSA-N 0.000 claims description 2
- HIQZNHHLMZDWAO-UHFFFAOYSA-N C(C(C)(C)C)[SiH](OCCOC)CC(C)(C)C Chemical compound C(C(C)(C)C)[SiH](OCCOC)CC(C)(C)C HIQZNHHLMZDWAO-UHFFFAOYSA-N 0.000 claims description 2
- UKXBFDYLINTJPO-UHFFFAOYSA-N C(C(C)(C)C)[SiH](OCCOC1=CC=CC=C1)CC(C)(C)C Chemical compound C(C(C)(C)C)[SiH](OCCOC1=CC=CC=C1)CC(C)(C)C UKXBFDYLINTJPO-UHFFFAOYSA-N 0.000 claims description 2
- XRVCTOHFEIQUFS-UHFFFAOYSA-N C(C)(C)(C)[SiH2]OCC(OC)OC Chemical compound C(C)(C)(C)[SiH2]OCC(OC)OC XRVCTOHFEIQUFS-UHFFFAOYSA-N 0.000 claims description 2
- PNIRQQROOAVUJP-UHFFFAOYSA-N C(C)(C)(C)[SiH2]OCC(OC1=CC=CC=C1)OC1=CC=CC=C1 Chemical compound C(C)(C)(C)[SiH2]OCC(OC1=CC=CC=C1)OC1=CC=CC=C1 PNIRQQROOAVUJP-UHFFFAOYSA-N 0.000 claims description 2
- UDJBWDQYIZTZQX-UHFFFAOYSA-N C(C)(C)(C)[SiH](OC1=CC=CC=C1)OCCOC Chemical compound C(C)(C)(C)[SiH](OC1=CC=CC=C1)OCCOC UDJBWDQYIZTZQX-UHFFFAOYSA-N 0.000 claims description 2
- QGECZDJYCWYWOJ-UHFFFAOYSA-N C(C)(C)(C)[SiH](OCCOC)C(C)(C)C Chemical compound C(C)(C)(C)[SiH](OCCOC)C(C)(C)C QGECZDJYCWYWOJ-UHFFFAOYSA-N 0.000 claims description 2
- QLZFABFKRDSFPW-UHFFFAOYSA-N C(C)(C)(C)[SiH](OCCOC1=CC=CC=C1)C(C)(C)C Chemical compound C(C)(C)(C)[SiH](OCCOC1=CC=CC=C1)C(C)(C)C QLZFABFKRDSFPW-UHFFFAOYSA-N 0.000 claims description 2
- FWYDWYSTULJHFC-UHFFFAOYSA-N C(C)(C)[SiH2]OCC(OC1=CC=CC=C1)OC1=CC=CC=C1 Chemical compound C(C)(C)[SiH2]OCC(OC1=CC=CC=C1)OC1=CC=CC=C1 FWYDWYSTULJHFC-UHFFFAOYSA-N 0.000 claims description 2
- VXMJBIUQMYDRRZ-UHFFFAOYSA-N C(C)(C)[SiH](OC1=CC=CC=C1)OCC1=CC=CC=C1 Chemical compound C(C)(C)[SiH](OC1=CC=CC=C1)OCC1=CC=CC=C1 VXMJBIUQMYDRRZ-UHFFFAOYSA-N 0.000 claims description 2
- NXBYZWXBLOWOQI-UHFFFAOYSA-N C(C)(C)[SiH](OC1=CC=CC=C1)OCCOC Chemical compound C(C)(C)[SiH](OC1=CC=CC=C1)OCCOC NXBYZWXBLOWOQI-UHFFFAOYSA-N 0.000 claims description 2
- ZIAUJMMNQYDTKY-UHFFFAOYSA-N C(C)(C)[SiH](OCCOC)C(C)C Chemical compound C(C)(C)[SiH](OCCOC)C(C)C ZIAUJMMNQYDTKY-UHFFFAOYSA-N 0.000 claims description 2
- LLOLAGQYIKBKDJ-UHFFFAOYSA-N C(C)(C)[SiH](OCCOC1=CC=CC=C1)C(C)C Chemical compound C(C)(C)[SiH](OCCOC1=CC=CC=C1)C(C)C LLOLAGQYIKBKDJ-UHFFFAOYSA-N 0.000 claims description 2
- SPRQFIYFGPITHF-UHFFFAOYSA-N C(C)(C)[SiH](OCCOC1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C(C)(C)[SiH](OCCOC1=CC=CC=C1)C1=CC=CC=C1 SPRQFIYFGPITHF-UHFFFAOYSA-N 0.000 claims description 2
- RAJNJRKDIONGHB-UHFFFAOYSA-N C(C)(C)[SiH](OCCOC1=CC=CC=C1)CC Chemical compound C(C)(C)[SiH](OCCOC1=CC=CC=C1)CC RAJNJRKDIONGHB-UHFFFAOYSA-N 0.000 claims description 2
- IXGUQRUJRKWVAR-UHFFFAOYSA-N C(C)[SiH](OC1=CC=CC=C1)OCC1=CC=CC=C1 Chemical compound C(C)[SiH](OC1=CC=CC=C1)OCC1=CC=CC=C1 IXGUQRUJRKWVAR-UHFFFAOYSA-N 0.000 claims description 2
- LSJPMKUZJFHLHM-UHFFFAOYSA-N C(C)[SiH](OCCOC1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C(C)[SiH](OCCOC1=CC=CC=C1)C1=CC=CC=C1 LSJPMKUZJFHLHM-UHFFFAOYSA-N 0.000 claims description 2
- YFXLUTGRZOMFDT-UHFFFAOYSA-N C(C)[SiH](OCCOC1=CC=CC=C1)C1CCCCC1 Chemical compound C(C)[SiH](OCCOC1=CC=CC=C1)C1CCCCC1 YFXLUTGRZOMFDT-UHFFFAOYSA-N 0.000 claims description 2
- FXQRYDSQXFNPJZ-UHFFFAOYSA-N C(C)[SiH](OCCOC1=CC=CC=C1)CC Chemical compound C(C)[SiH](OCCOC1=CC=CC=C1)CC FXQRYDSQXFNPJZ-UHFFFAOYSA-N 0.000 claims description 2
- LSVIISFRSKMBJU-UHFFFAOYSA-N C(C1=CC=CC=C1)[SiH2]OCC(OC)OC Chemical compound C(C1=CC=CC=C1)[SiH2]OCC(OC)OC LSVIISFRSKMBJU-UHFFFAOYSA-N 0.000 claims description 2
- LTCGMPRWTQSZAP-UHFFFAOYSA-N C(C1=CC=CC=C1)[SiH2]OCC(OC1=CC=CC=C1)OC1=CC=CC=C1 Chemical compound C(C1=CC=CC=C1)[SiH2]OCC(OC1=CC=CC=C1)OC1=CC=CC=C1 LTCGMPRWTQSZAP-UHFFFAOYSA-N 0.000 claims description 2
- DOSOSNGSQAVYMN-UHFFFAOYSA-N C(C1=CC=CC=C1)[SiH](OCCOC1=CC=CC=C1)CC1=CC=CC=C1 Chemical compound C(C1=CC=CC=C1)[SiH](OCCOC1=CC=CC=C1)CC1=CC=CC=C1 DOSOSNGSQAVYMN-UHFFFAOYSA-N 0.000 claims description 2
- KVLSCIYIYPJXMS-UHFFFAOYSA-N C(CC)[SiH](OCCOC1=CC=CC=C1)CCC Chemical compound C(CC)[SiH](OCCOC1=CC=CC=C1)CCC KVLSCIYIYPJXMS-UHFFFAOYSA-N 0.000 claims description 2
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- CFPFSGNIHZMRRQ-UHFFFAOYSA-N C(CCC)[SiH](OC1=CC=CC=C1)OCCOC Chemical compound C(CCC)[SiH](OC1=CC=CC=C1)OCCOC CFPFSGNIHZMRRQ-UHFFFAOYSA-N 0.000 claims description 2
- QSGSXOKEFULGNO-UHFFFAOYSA-N C(CCC)[SiH](OCCOC1=CC=CC=C1)CCCC Chemical compound C(CCC)[SiH](OCCOC1=CC=CC=C1)CCCC QSGSXOKEFULGNO-UHFFFAOYSA-N 0.000 claims description 2
- ZBTZKPSEUNLADJ-UHFFFAOYSA-N C(CCCC)[SiH2]OCC(OC)OC Chemical compound C(CCCC)[SiH2]OCC(OC)OC ZBTZKPSEUNLADJ-UHFFFAOYSA-N 0.000 claims description 2
- GXRHITAXDONGJE-UHFFFAOYSA-N C(CCCC)[SiH](OCCOC1=CC=CC=C1)CCCCC Chemical compound C(CCCC)[SiH](OCCOC1=CC=CC=C1)CCCCC GXRHITAXDONGJE-UHFFFAOYSA-N 0.000 claims description 2
- BWZQEKWQUDYHEX-UHFFFAOYSA-N C(CCCCC)[SiH](OC1=CC=CC=C1)OCCOC Chemical compound C(CCCCC)[SiH](OC1=CC=CC=C1)OCCOC BWZQEKWQUDYHEX-UHFFFAOYSA-N 0.000 claims description 2
- WSIOSYBRBKXPTR-UHFFFAOYSA-N C(CCCCC)[SiH](OCCOC)CCCCCC Chemical compound C(CCCCC)[SiH](OCCOC)CCCCCC WSIOSYBRBKXPTR-UHFFFAOYSA-N 0.000 claims description 2
- HNJYRJKGGJTOGM-UHFFFAOYSA-N C(CCCCC)[SiH](OCCOC1=CC=CC=C1)CCCCCC Chemical compound C(CCCCC)[SiH](OCCOC1=CC=CC=C1)CCCCCC HNJYRJKGGJTOGM-UHFFFAOYSA-N 0.000 claims description 2
- DEYGRYQMTWOUDM-UHFFFAOYSA-N C1(=CC=CC=C1)C(O[SiH2]OC1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C(O[SiH2]OC1=CC=CC=C1)C1=CC=CC=C1 DEYGRYQMTWOUDM-UHFFFAOYSA-N 0.000 claims description 2
- HCJRWNXZNBNZBW-UHFFFAOYSA-N C1(CCCCC1)C(OCCO[SiH3])C1CCCCC1 Chemical compound C1(CCCCC1)C(OCCO[SiH3])C1CCCCC1 HCJRWNXZNBNZBW-UHFFFAOYSA-N 0.000 claims description 2
- BKTVGRGNQVQUKS-UHFFFAOYSA-N C1(CCCCC1)[SiH2]OCC(OC1=CC=CC=C1)OC1=CC=CC=C1 Chemical compound C1(CCCCC1)[SiH2]OCC(OC1=CC=CC=C1)OC1=CC=CC=C1 BKTVGRGNQVQUKS-UHFFFAOYSA-N 0.000 claims description 2
- ZUASYXSEPGXVKI-UHFFFAOYSA-N C1(CCCCC1)[SiH](OCCOC1=CC=CC=C1)C1CCCCC1 Chemical compound C1(CCCCC1)[SiH](OCCOC1=CC=CC=C1)C1CCCCC1 ZUASYXSEPGXVKI-UHFFFAOYSA-N 0.000 claims description 2
- MPGSZCUOCZXINF-UHFFFAOYSA-N C1CCCCC1C(C1CCCCC1)(CO[SiH3])C1CCCCC1 Chemical compound C1CCCCC1C(C1CCCCC1)(CO[SiH3])C1CCCCC1 MPGSZCUOCZXINF-UHFFFAOYSA-N 0.000 claims description 2
- VDNLLHMLTVHGSC-UHFFFAOYSA-N C[SiH](OC1=CC=CC=C1)OCC1=CC=CC=C1 Chemical compound C[SiH](OC1=CC=CC=C1)OCC1=CC=CC=C1 VDNLLHMLTVHGSC-UHFFFAOYSA-N 0.000 claims description 2
- MHTKASPNMGBHNS-UHFFFAOYSA-N C[SiH](OCCOC)C(C)C Chemical compound C[SiH](OCCOC)C(C)C MHTKASPNMGBHNS-UHFFFAOYSA-N 0.000 claims description 2
- IMDVCXKVIVEROU-UHFFFAOYSA-N C[SiH](OCCOC1=CC=CC=C1)C(C)C Chemical compound C[SiH](OCCOC1=CC=CC=C1)C(C)C IMDVCXKVIVEROU-UHFFFAOYSA-N 0.000 claims description 2
- FQARIBYWQSPYPZ-UHFFFAOYSA-N benzhydryloxy(ethyl)silane Chemical compound C(C)[SiH2]OC(C1=CC=CC=C1)C1=CC=CC=C1 FQARIBYWQSPYPZ-UHFFFAOYSA-N 0.000 claims description 2
- AUJBFOAFSMIJQP-UHFFFAOYSA-N benzhydryloxy(propan-2-yl)silane Chemical compound C=1C=CC=CC=1C(O[SiH2]C(C)C)C1=CC=CC=C1 AUJBFOAFSMIJQP-UHFFFAOYSA-N 0.000 claims description 2
- CPLASELWOOUNGW-UHFFFAOYSA-N benzyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CC1=CC=CC=C1 CPLASELWOOUNGW-UHFFFAOYSA-N 0.000 claims description 2
- GQVVQDJHRQBZNG-UHFFFAOYSA-N benzyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CC1=CC=CC=C1 GQVVQDJHRQBZNG-UHFFFAOYSA-N 0.000 claims description 2
- WYPVCNAWOFJQTA-UHFFFAOYSA-N benzyl(triphenoxy)silane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(OC=1C=CC=CC=1)CC1=CC=CC=C1 WYPVCNAWOFJQTA-UHFFFAOYSA-N 0.000 claims description 2
- YMMZXIUYTWRDGL-UHFFFAOYSA-N benzyl-dimethoxy-phenoxysilane Chemical compound C=1C=CC=CC=1O[Si](OC)(OC)CC1=CC=CC=C1 YMMZXIUYTWRDGL-UHFFFAOYSA-N 0.000 claims description 2
- LJZANYXLJBPXJL-UHFFFAOYSA-N bis(2,2-dimethylpropyl)-diphenoxysilane Chemical compound C(C(C)(C)C)[Si](OC1=CC=CC=C1)(OC1=CC=CC=C1)CC(C)(C)C LJZANYXLJBPXJL-UHFFFAOYSA-N 0.000 claims description 2
- WTKYFMFHWGZJFH-UHFFFAOYSA-N bis(2,2-dimethylpropyl)-methoxy-phenoxysilane Chemical compound C(C(C)(C)C)[Si](OC1=CC=CC=C1)(OC)CC(C)(C)C WTKYFMFHWGZJFH-UHFFFAOYSA-N 0.000 claims description 2
- ZPWWJMULPQKGQK-UHFFFAOYSA-N butyl(2,2-dimethoxyethoxy)silane Chemical compound C(CCC)[SiH2]OCC(OC)OC ZPWWJMULPQKGQK-UHFFFAOYSA-N 0.000 claims description 2
- XGZGKDQVCBHSGI-UHFFFAOYSA-N butyl(triethoxy)silane Chemical compound CCCC[Si](OCC)(OCC)OCC XGZGKDQVCBHSGI-UHFFFAOYSA-N 0.000 claims description 2
- SXPLZNMUBFBFIA-UHFFFAOYSA-N butyl(trimethoxy)silane Chemical compound CCCC[Si](OC)(OC)OC SXPLZNMUBFBFIA-UHFFFAOYSA-N 0.000 claims description 2
- OGCNPMTZBJEZKT-UHFFFAOYSA-N butyl(triphenoxy)silane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(CCCC)OC1=CC=CC=C1 OGCNPMTZBJEZKT-UHFFFAOYSA-N 0.000 claims description 2
- PNJFAHGOTMPLGN-UHFFFAOYSA-N butyl-dimethoxy-phenoxysilane Chemical compound C(CCC)[Si](OC1=CC=CC=C1)(OC)OC PNJFAHGOTMPLGN-UHFFFAOYSA-N 0.000 claims description 2
- RNAWUQLXHGVHDQ-UHFFFAOYSA-N cyclohexyl(2,2-dimethoxyethoxy)silane Chemical compound COC(CO[SiH2]C1CCCCC1)OC RNAWUQLXHGVHDQ-UHFFFAOYSA-N 0.000 claims description 2
- ATGKAFZFOALBOF-UHFFFAOYSA-N cyclohexyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C1CCCCC1 ATGKAFZFOALBOF-UHFFFAOYSA-N 0.000 claims description 2
- MEWFSXFFGFDHGV-UHFFFAOYSA-N cyclohexyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C1CCCCC1 MEWFSXFFGFDHGV-UHFFFAOYSA-N 0.000 claims description 2
- XARPZDLCPBWSCT-UHFFFAOYSA-N cyclohexyl(triphenoxy)silane Chemical compound C1CCCCC1[Si](OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 XARPZDLCPBWSCT-UHFFFAOYSA-N 0.000 claims description 2
- SFEWPQUOONCGJP-UHFFFAOYSA-N cyclohexyl-diethoxy-ethylsilane Chemical compound CCO[Si](CC)(OCC)C1CCCCC1 SFEWPQUOONCGJP-UHFFFAOYSA-N 0.000 claims description 2
- QQMPKEQPHWEWPI-UHFFFAOYSA-N cyclohexyl-diethyl-phenoxysilane Chemical compound C(C)[Si](OC1=CC=CC=C1)(C1CCCCC1)CC QQMPKEQPHWEWPI-UHFFFAOYSA-N 0.000 claims description 2
- SJJCABYOVIHNPZ-UHFFFAOYSA-N cyclohexyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C1CCCCC1 SJJCABYOVIHNPZ-UHFFFAOYSA-N 0.000 claims description 2
- BBILQZQIPCABRH-UHFFFAOYSA-N cyclohexyl-dimethoxy-phenoxysilane Chemical compound C1(CCCCC1)[Si](OC1=CC=CC=C1)(OC)OC BBILQZQIPCABRH-UHFFFAOYSA-N 0.000 claims description 2
- GUKACAXTTXKTBN-UHFFFAOYSA-N cyclohexyl-dimethyl-phenoxysilane Chemical compound C1CCCCC1[Si](C)(C)OC1=CC=CC=C1 GUKACAXTTXKTBN-UHFFFAOYSA-N 0.000 claims description 2
- ITLGODSMZYIBRF-UHFFFAOYSA-N cyclohexyl-ethoxy-methoxy-methylsilane Chemical compound CCO[Si](C)(OC)C1CCCCC1 ITLGODSMZYIBRF-UHFFFAOYSA-N 0.000 claims description 2
- VVYHLAFQVXSUOR-UHFFFAOYSA-N cyclohexyl-ethoxy-methyl-phenoxysilane Chemical compound C[Si](OCC)(OC1=CC=CC=C1)C1CCCCC1 VVYHLAFQVXSUOR-UHFFFAOYSA-N 0.000 claims description 2
- QEPVYYOIYSITJK-UHFFFAOYSA-N cyclohexyl-ethyl-dimethoxysilane Chemical compound CC[Si](OC)(OC)C1CCCCC1 QEPVYYOIYSITJK-UHFFFAOYSA-N 0.000 claims description 2
- YOLAWMDIIPORDU-UHFFFAOYSA-N cyclohexyl-ethyl-diphenoxysilane Chemical compound C(C)[Si](OC1=CC=CC=C1)(OC1=CC=CC=C1)C1CCCCC1 YOLAWMDIIPORDU-UHFFFAOYSA-N 0.000 claims description 2
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- IEBSAWPPCGOABJ-UHFFFAOYSA-N cyclohexyl-methyl-diphenoxysilane Chemical compound C[Si](OC1=CC=CC=C1)(OC1=CC=CC=C1)C1CCCCC1 IEBSAWPPCGOABJ-UHFFFAOYSA-N 0.000 claims description 2
- NBHLGURMXJHIOD-UHFFFAOYSA-N dibenzyl(dimethoxy)silane Chemical compound C=1C=CC=CC=1C[Si](OC)(OC)CC1=CC=CC=C1 NBHLGURMXJHIOD-UHFFFAOYSA-N 0.000 claims description 2
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- DGPFXVBYDAVXLX-UHFFFAOYSA-N dibutyl(diethoxy)silane Chemical compound CCCC[Si](OCC)(OCC)CCCC DGPFXVBYDAVXLX-UHFFFAOYSA-N 0.000 claims description 2
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- QDMXGHLVHDTPAA-UHFFFAOYSA-N dibutyl(diphenoxy)silane Chemical compound C=1C=CC=CC=1O[Si](CCCC)(CCCC)OC1=CC=CC=C1 QDMXGHLVHDTPAA-UHFFFAOYSA-N 0.000 claims description 2
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- CGYGEZLIGMBRKL-UHFFFAOYSA-N dicyclohexyl(diethoxy)silane Chemical compound C1CCCCC1[Si](OCC)(OCC)C1CCCCC1 CGYGEZLIGMBRKL-UHFFFAOYSA-N 0.000 claims description 2
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- ZMAPKOCENOWQRE-UHFFFAOYSA-N diethoxy(diethyl)silane Chemical compound CCO[Si](CC)(CC)OCC ZMAPKOCENOWQRE-UHFFFAOYSA-N 0.000 claims description 2
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- VDXFKFNGIDWIQQ-UHFFFAOYSA-N diethoxy(dipentyl)silane Chemical compound CCCCC[Si](OCC)(OCC)CCCCC VDXFKFNGIDWIQQ-UHFFFAOYSA-N 0.000 claims description 2
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- MNFGEHQPOWJJBH-UHFFFAOYSA-N diethoxy-methyl-phenylsilane Chemical compound CCO[Si](C)(OCC)C1=CC=CC=C1 MNFGEHQPOWJJBH-UHFFFAOYSA-N 0.000 claims description 2
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- JCBICQPQDXICCD-UHFFFAOYSA-N diethyl(2-methoxyethoxy)silane Chemical compound C(C)[SiH](OCCOC)CC JCBICQPQDXICCD-UHFFFAOYSA-N 0.000 claims description 2
- VSYLGGHSEIWGJV-UHFFFAOYSA-N diethyl(dimethoxy)silane Chemical compound CC[Si](CC)(OC)OC VSYLGGHSEIWGJV-UHFFFAOYSA-N 0.000 claims description 2
- UFWOWQYGXPYINE-UHFFFAOYSA-N diethyl(diphenoxy)silane Chemical compound C=1C=CC=CC=1O[Si](CC)(CC)OC1=CC=CC=C1 UFWOWQYGXPYINE-UHFFFAOYSA-N 0.000 claims description 2
- QGGXICROBGLDJO-UHFFFAOYSA-N diethyl-methoxy-phenoxysilane Chemical compound C(C)[Si](OC1=CC=CC=C1)(OC)CC QGGXICROBGLDJO-UHFFFAOYSA-N 0.000 claims description 2
- ITXWIQSMBXVEFT-UHFFFAOYSA-N diethyl-methoxy-propan-2-ylsilane Chemical compound CC[Si](CC)(OC)C(C)C ITXWIQSMBXVEFT-UHFFFAOYSA-N 0.000 claims description 2
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- CYICXDQJFWXGTC-UHFFFAOYSA-N dihexyl(dimethoxy)silane Chemical compound CCCCCC[Si](OC)(OC)CCCCCC CYICXDQJFWXGTC-UHFFFAOYSA-N 0.000 claims description 2
- PREPMXBOIFNENA-UHFFFAOYSA-N dihexyl(diphenoxy)silane Chemical compound C=1C=CC=CC=1O[Si](CCCCCC)(CCCCCC)OC1=CC=CC=C1 PREPMXBOIFNENA-UHFFFAOYSA-N 0.000 claims description 2
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- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 claims description 2
- LXAPXYULCIKKNK-UHFFFAOYSA-N dimethoxy(dipentyl)silane Chemical compound CCCCC[Si](OC)(OC)CCCCC LXAPXYULCIKKNK-UHFFFAOYSA-N 0.000 claims description 2
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 claims description 2
- JVUVKQDVTIIMOD-UHFFFAOYSA-N dimethoxy(dipropyl)silane Chemical compound CCC[Si](OC)(OC)CCC JVUVKQDVTIIMOD-UHFFFAOYSA-N 0.000 claims description 2
- IWYYJESDAIBNJJ-UHFFFAOYSA-N dimethoxy-methyl-phenoxysilane Chemical compound CO[Si](C)(OC)OC1=CC=CC=C1 IWYYJESDAIBNJJ-UHFFFAOYSA-N 0.000 claims description 2
- CVQVSVBUMVSJES-UHFFFAOYSA-N dimethoxy-methyl-phenylsilane Chemical compound CO[Si](C)(OC)C1=CC=CC=C1 CVQVSVBUMVSJES-UHFFFAOYSA-N 0.000 claims description 2
- XZFXULUXIPPWEW-UHFFFAOYSA-N dimethoxy-methyl-propan-2-ylsilane Chemical compound CO[Si](C)(OC)C(C)C XZFXULUXIPPWEW-UHFFFAOYSA-N 0.000 claims description 2
- PXVCUWJWHYYFEY-UHFFFAOYSA-N dimethoxy-pentyl-phenoxysilane Chemical compound C(CCCC)[Si](OC1=CC=CC=C1)(OC)OC PXVCUWJWHYYFEY-UHFFFAOYSA-N 0.000 claims description 2
- SZEPYCRHBJIIQP-UHFFFAOYSA-N dimethoxy-phenoxy-propan-2-ylsilane Chemical compound C(C)(C)[Si](OC1=CC=CC=C1)(OC)OC SZEPYCRHBJIIQP-UHFFFAOYSA-N 0.000 claims description 2
- ULABDCHEKCEDON-UHFFFAOYSA-N dimethoxy-phenyl-propan-2-ylsilane Chemical compound CO[Si](OC)(C(C)C)C1=CC=CC=C1 ULABDCHEKCEDON-UHFFFAOYSA-N 0.000 claims description 2
- RJQDIIOADIEYLW-UHFFFAOYSA-N dimethyl(2-phenoxyethoxy)silane Chemical compound C[SiH](OCCOC1=CC=CC=C1)C RJQDIIOADIEYLW-UHFFFAOYSA-N 0.000 claims description 2
- DVYUOQXRGHUWKE-UHFFFAOYSA-N dimethyl(2-phenylethoxy)silane Chemical compound C[SiH](C)OCCC1=CC=CC=C1 DVYUOQXRGHUWKE-UHFFFAOYSA-N 0.000 claims description 2
- SWLVAJXQIOKFSJ-UHFFFAOYSA-N dimethyl(diphenoxy)silane Chemical compound C=1C=CC=CC=1O[Si](C)(C)OC1=CC=CC=C1 SWLVAJXQIOKFSJ-UHFFFAOYSA-N 0.000 claims description 2
- SZPIKCAXBLKNNK-UHFFFAOYSA-N dimethyl-phenoxy-phenylsilane Chemical compound C=1C=CC=CC=1[Si](C)(C)OC1=CC=CC=C1 SZPIKCAXBLKNNK-UHFFFAOYSA-N 0.000 claims description 2
- DNXRKJUPQDVPKP-UHFFFAOYSA-N dimethyl-phenoxy-propan-2-ylsilane Chemical compound CC(C)[Si](C)(C)OC1=CC=CC=C1 DNXRKJUPQDVPKP-UHFFFAOYSA-N 0.000 claims description 2
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 claims description 2
- VZRFBNIRAWEORG-UHFFFAOYSA-N dipentyl(diphenoxy)silane Chemical compound C=1C=CC=CC=1O[Si](CCCCC)(CCCCC)OC1=CC=CC=C1 VZRFBNIRAWEORG-UHFFFAOYSA-N 0.000 claims description 2
- YLDKQPMORVEBRU-UHFFFAOYSA-N diphenoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1O[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)OC1=CC=CC=C1 YLDKQPMORVEBRU-UHFFFAOYSA-N 0.000 claims description 2
- JFCVQVCWZYWWPV-UHFFFAOYSA-N diphenoxy(dipropyl)silane Chemical compound C=1C=CC=CC=1O[Si](CCC)(CCC)OC1=CC=CC=C1 JFCVQVCWZYWWPV-UHFFFAOYSA-N 0.000 claims description 2
- JPKFEPIUGPNLAR-UHFFFAOYSA-N diphenoxy-di(propan-2-yl)silane Chemical compound C=1C=CC=CC=1O[Si](C(C)C)(C(C)C)OC1=CC=CC=C1 JPKFEPIUGPNLAR-UHFFFAOYSA-N 0.000 claims description 2
- PBHPGPBQCUZMRJ-UHFFFAOYSA-N diphenoxy-phenyl-propan-2-ylsilane Chemical compound C=1C=CC=CC=1O[Si](C=1C=CC=CC=1)(C(C)C)OC1=CC=CC=C1 PBHPGPBQCUZMRJ-UHFFFAOYSA-N 0.000 claims description 2
- GWCASPKBFBALDG-UHFFFAOYSA-N ditert-butyl(diethoxy)silane Chemical compound CCO[Si](C(C)(C)C)(C(C)(C)C)OCC GWCASPKBFBALDG-UHFFFAOYSA-N 0.000 claims description 2
- OANIYCQMEVXZCJ-UHFFFAOYSA-N ditert-butyl(dimethoxy)silane Chemical compound CO[Si](OC)(C(C)(C)C)C(C)(C)C OANIYCQMEVXZCJ-UHFFFAOYSA-N 0.000 claims description 2
- WOMHHBWXYINIPW-UHFFFAOYSA-N ditert-butyl(diphenoxy)silane Chemical compound C=1C=CC=CC=1O[Si](C(C)(C)C)(C(C)(C)C)OC1=CC=CC=C1 WOMHHBWXYINIPW-UHFFFAOYSA-N 0.000 claims description 2
- URXQKROOPZXLIA-UHFFFAOYSA-N ditert-butyl-methoxy-phenoxysilane Chemical compound C(C)(C)(C)[Si](OC1=CC=CC=C1)(OC)C(C)(C)C URXQKROOPZXLIA-UHFFFAOYSA-N 0.000 claims description 2
- DFJDZTPFNSXNAX-UHFFFAOYSA-N ethoxy(triethyl)silane Chemical compound CCO[Si](CC)(CC)CC DFJDZTPFNSXNAX-UHFFFAOYSA-N 0.000 claims description 2
- MMEIWOLDAQXGAR-UHFFFAOYSA-N ethoxy(trihexyl)silane Chemical compound CCCCCC[Si](CCCCCC)(CCCCCC)OCC MMEIWOLDAQXGAR-UHFFFAOYSA-N 0.000 claims description 2
- RSIHJDGMBDPTIM-UHFFFAOYSA-N ethoxy(trimethyl)silane Chemical compound CCO[Si](C)(C)C RSIHJDGMBDPTIM-UHFFFAOYSA-N 0.000 claims description 2
- AIQINSYMXZQEBE-UHFFFAOYSA-N ethoxy(tripentyl)silane Chemical compound CCCCC[Si](CCCCC)(CCCCC)OCC AIQINSYMXZQEBE-UHFFFAOYSA-N 0.000 claims description 2
- ZVJXKUWNRVOUTI-UHFFFAOYSA-N ethoxy(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(OCC)C1=CC=CC=C1 ZVJXKUWNRVOUTI-UHFFFAOYSA-N 0.000 claims description 2
- TXLQMNVUTSCJOB-UHFFFAOYSA-N ethoxy-diethyl-propan-2-ylsilane Chemical compound CCO[Si](CC)(CC)C(C)C TXLQMNVUTSCJOB-UHFFFAOYSA-N 0.000 claims description 2
- FKDLBUPSJQZYFZ-UHFFFAOYSA-N ethoxy-ethyl-dimethylsilane Chemical compound CCO[Si](C)(C)CC FKDLBUPSJQZYFZ-UHFFFAOYSA-N 0.000 claims description 2
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 claims description 2
- HGWSCXYVBZYYDK-UHFFFAOYSA-N ethyl(triphenoxy)silane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(CC)OC1=CC=CC=C1 HGWSCXYVBZYYDK-UHFFFAOYSA-N 0.000 claims description 2
- CMKWTALNNHIPBQ-UHFFFAOYSA-N ethyl-(2-methoxyethoxy)-phenoxysilane Chemical compound C(C)[SiH](OC1=CC=CC=C1)OCCOC CMKWTALNNHIPBQ-UHFFFAOYSA-N 0.000 claims description 2
- MKHRQNSNGGSFPO-UHFFFAOYSA-N ethyl-(2-methoxyethoxy)-propan-2-ylsilane Chemical compound C(C)[SiH](OCCOC)C(C)C MKHRQNSNGGSFPO-UHFFFAOYSA-N 0.000 claims description 2
- HTSRFYSEWIPFNI-UHFFFAOYSA-N ethyl-dimethoxy-methylsilane Chemical compound CC[Si](C)(OC)OC HTSRFYSEWIPFNI-UHFFFAOYSA-N 0.000 claims description 2
- COIHYPMFNWPRSV-UHFFFAOYSA-N ethyl-dimethoxy-phenoxysilane Chemical compound CC[Si](OC)(OC)OC1=CC=CC=C1 COIHYPMFNWPRSV-UHFFFAOYSA-N 0.000 claims description 2
- OWFNNCHTAVHPBL-UHFFFAOYSA-N ethyl-dimethoxy-phenylsilane Chemical compound CC[Si](OC)(OC)C1=CC=CC=C1 OWFNNCHTAVHPBL-UHFFFAOYSA-N 0.000 claims description 2
- JNGLVADKXYIWAE-UHFFFAOYSA-N ethyl-dimethoxy-propan-2-ylsilane Chemical compound CC[Si](OC)(OC)C(C)C JNGLVADKXYIWAE-UHFFFAOYSA-N 0.000 claims description 2
- SHGFHXXFGSYRPM-UHFFFAOYSA-N ethyl-dimethyl-phenoxysilane Chemical compound CC[Si](C)(C)OC1=CC=CC=C1 SHGFHXXFGSYRPM-UHFFFAOYSA-N 0.000 claims description 2
- RKSPWRTZCCQTFC-UHFFFAOYSA-N ethyl-diphenoxy-propan-2-ylsilane Chemical compound C(C)(C)[Si](OC1=CC=CC=C1)(OC1=CC=CC=C1)CC RKSPWRTZCCQTFC-UHFFFAOYSA-N 0.000 claims description 2
- SUHRFYWSDBWMFS-UHFFFAOYSA-N ethyl-methoxy-dimethylsilane Chemical compound CC[Si](C)(C)OC SUHRFYWSDBWMFS-UHFFFAOYSA-N 0.000 claims description 2
- PJFNABSHHQQWEA-UHFFFAOYSA-N ethyl-methoxy-methyl-phenoxysilane Chemical compound CC[Si](C)(OC)Oc1ccccc1 PJFNABSHHQQWEA-UHFFFAOYSA-N 0.000 claims description 2
- DPIZYYFAOIZTTG-UHFFFAOYSA-N ethyl-methoxy-phenoxy-propan-2-ylsilane Chemical compound C(C)(C)[Si](OC1=CC=CC=C1)(OC)CC DPIZYYFAOIZTTG-UHFFFAOYSA-N 0.000 claims description 2
- GIOUGOVEOZETDS-UHFFFAOYSA-N ethyl-methyl-(2-phenoxyethoxy)silane Chemical compound C(C)[SiH](OCCOC1=CC=CC=C1)C GIOUGOVEOZETDS-UHFFFAOYSA-N 0.000 claims description 2
- DNZFXAXSKBVILN-UHFFFAOYSA-N ethyl-phenoxy-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(CC)OC1=CC=CC=C1 DNZFXAXSKBVILN-UHFFFAOYSA-N 0.000 claims description 2
- CZWLNMOIEMTDJY-UHFFFAOYSA-N hexyl(trimethoxy)silane Chemical compound CCCCCC[Si](OC)(OC)OC CZWLNMOIEMTDJY-UHFFFAOYSA-N 0.000 claims description 2
- UJINUQJBFQVWEW-UHFFFAOYSA-N hexyl(triphenoxy)silane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(CCCCCC)OC1=CC=CC=C1 UJINUQJBFQVWEW-UHFFFAOYSA-N 0.000 claims description 2
- IMSRDAUGQHERCT-UHFFFAOYSA-N hexyl-dimethoxy-phenoxysilane Chemical compound C(CCCCC)[Si](OC1=CC=CC=C1)(OC)OC IMSRDAUGQHERCT-UHFFFAOYSA-N 0.000 claims description 2
- POPACFLNWGUDSR-UHFFFAOYSA-N methoxy(trimethyl)silane Chemical compound CO[Si](C)(C)C POPACFLNWGUDSR-UHFFFAOYSA-N 0.000 claims description 2
- RRZGEHWVNQWBLW-UHFFFAOYSA-N methoxy(tripentyl)silane Chemical compound CCCCC[Si](CCCCC)(CCCCC)OC RRZGEHWVNQWBLW-UHFFFAOYSA-N 0.000 claims description 2
- BKXVGDZNDSIUAI-UHFFFAOYSA-N methoxy(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(OC)C1=CC=CC=C1 BKXVGDZNDSIUAI-UHFFFAOYSA-N 0.000 claims description 2
- FUMSHFZKHQOOIX-UHFFFAOYSA-N methoxy(tripropyl)silane Chemical compound CCC[Si](CCC)(CCC)OC FUMSHFZKHQOOIX-UHFFFAOYSA-N 0.000 claims description 2
- NHDNAWSZKWNPIN-UHFFFAOYSA-N methoxy-dimethyl-phenoxysilane Chemical compound CO[Si](C)(C)OC1=CC=CC=C1 NHDNAWSZKWNPIN-UHFFFAOYSA-N 0.000 claims description 2
- REQXNMOSXYEQLM-UHFFFAOYSA-N methoxy-dimethyl-phenylsilane Chemical compound CO[Si](C)(C)C1=CC=CC=C1 REQXNMOSXYEQLM-UHFFFAOYSA-N 0.000 claims description 2
- JEVKJXTUCCLSOP-UHFFFAOYSA-N methoxy-dipentyl-phenoxysilane Chemical compound C(CCCC)[Si](OC1=CC=CC=C1)(OC)CCCCC JEVKJXTUCCLSOP-UHFFFAOYSA-N 0.000 claims description 2
- BGDIYFASEYXOQB-UHFFFAOYSA-N methoxy-methyl-phenoxy-propan-2-ylsilane Chemical compound C[Si](OC1=CC=CC=C1)(OC)C(C)C BGDIYFASEYXOQB-UHFFFAOYSA-N 0.000 claims description 2
- IXFWOXNNHKWXAM-UHFFFAOYSA-N methoxy-phenoxy-di(propan-2-yl)silane Chemical compound C(C)(C)[Si](OC1=CC=CC=C1)(OC)C(C)C IXFWOXNNHKWXAM-UHFFFAOYSA-N 0.000 claims description 2
- LQWWFXYINKSKLF-UHFFFAOYSA-N methoxy-phenoxy-dipropylsilane Chemical compound C(CC)[Si](OC1=CC=CC=C1)(OC)CCC LQWWFXYINKSKLF-UHFFFAOYSA-N 0.000 claims description 2
- YKFVVAUPACHDIG-UHFFFAOYSA-N methoxy-tri(propan-2-yl)silane Chemical compound CO[Si](C(C)C)(C(C)C)C(C)C YKFVVAUPACHDIG-UHFFFAOYSA-N 0.000 claims description 2
- WJOUKUZVWNZOSE-UHFFFAOYSA-N methyl(2-phenylmethoxyethoxy)silane Chemical compound C[SiH2]OCCOCC1=CC=CC=C1 WJOUKUZVWNZOSE-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 150000002513 isocyanates Chemical class 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
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- 239000006233 lamp black Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
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- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 229910012375 magnesium hydride Inorganic materials 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
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- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- WRYKIHMRDIOPSI-UHFFFAOYSA-N magnesium;benzene Chemical compound [Mg+2].C1=CC=[C-]C=C1.C1=CC=[C-]C=C1 WRYKIHMRDIOPSI-UHFFFAOYSA-N 0.000 description 1
- KJJBSBKRXUVBMX-UHFFFAOYSA-N magnesium;butane Chemical compound [Mg+2].CCC[CH2-].CCC[CH2-] KJJBSBKRXUVBMX-UHFFFAOYSA-N 0.000 description 1
- QUXHCILOWRXCEO-UHFFFAOYSA-M magnesium;butane;chloride Chemical compound [Mg+2].[Cl-].CCC[CH2-] QUXHCILOWRXCEO-UHFFFAOYSA-M 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- DLPASUVGCQPFFO-UHFFFAOYSA-N magnesium;ethane Chemical compound [Mg+2].[CH2-]C.[CH2-]C DLPASUVGCQPFFO-UHFFFAOYSA-N 0.000 description 1
- RVOYYLUVELMWJF-UHFFFAOYSA-N magnesium;hexane Chemical compound [Mg+2].CCCCC[CH2-].CCCCC[CH2-] RVOYYLUVELMWJF-UHFFFAOYSA-N 0.000 description 1
- LZFCBBSYZJPPIV-UHFFFAOYSA-M magnesium;hexane;bromide Chemical compound [Mg+2].[Br-].CCCCC[CH2-] LZFCBBSYZJPPIV-UHFFFAOYSA-M 0.000 description 1
- GBRJQTLHXWRDOV-UHFFFAOYSA-M magnesium;hexane;chloride Chemical compound [Mg+2].[Cl-].CCCCC[CH2-] GBRJQTLHXWRDOV-UHFFFAOYSA-M 0.000 description 1
- WCFJMDWWJOCLSJ-UHFFFAOYSA-N magnesium;methanidylbenzene Chemical compound [Mg+2].[CH2-]C1=CC=CC=C1.[CH2-]C1=CC=CC=C1 WCFJMDWWJOCLSJ-UHFFFAOYSA-N 0.000 description 1
- QGEFGPVWRJCFQP-UHFFFAOYSA-M magnesium;methanidylbenzene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C1=CC=CC=C1 QGEFGPVWRJCFQP-UHFFFAOYSA-M 0.000 description 1
- DQZLQYHGCKLKGU-UHFFFAOYSA-N magnesium;propane Chemical compound [Mg+2].C[CH-]C.C[CH-]C DQZLQYHGCKLKGU-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 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
- 229910052752 metalloid Inorganic materials 0.000 description 1
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- CBNHBSGOXOSEAO-UHFFFAOYSA-N methanolate neodymium(3+) Chemical compound [Nd+3].[O-]C.[O-]C.[O-]C CBNHBSGOXOSEAO-UHFFFAOYSA-N 0.000 description 1
- NEMYBHYAISOMTI-UHFFFAOYSA-N methanolate;2-methylpropylaluminum(2+) Chemical compound [O-]C.[O-]C.CC(C)C[Al+2] NEMYBHYAISOMTI-UHFFFAOYSA-N 0.000 description 1
- DKUIXLPCCDROFD-UHFFFAOYSA-N methanolate;methylaluminum(2+) Chemical compound [O-]C.[O-]C.[Al+2]C DKUIXLPCCDROFD-UHFFFAOYSA-N 0.000 description 1
- BQBCXNQILNPAPX-UHFFFAOYSA-N methoxy(dimethyl)alumane Chemical compound [O-]C.C[Al+]C BQBCXNQILNPAPX-UHFFFAOYSA-N 0.000 description 1
- RWIKCBHOVNDESJ-NSCUHMNNSA-N methyl (e)-4-bromobut-2-enoate Chemical compound COC(=O)\C=C\CBr RWIKCBHOVNDESJ-NSCUHMNNSA-N 0.000 description 1
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
- SWGQITQOBPXVRC-UHFFFAOYSA-N methyl 2-bromobenzoate Chemical compound COC(=O)C1=CC=CC=C1Br SWGQITQOBPXVRC-UHFFFAOYSA-N 0.000 description 1
- UFQQDNMQADCHGH-UHFFFAOYSA-N methyl 2-bromobutanoate Chemical compound CCC(Br)C(=O)OC UFQQDNMQADCHGH-UHFFFAOYSA-N 0.000 description 1
- ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 description 1
- KMFJVYMFCAIRAN-UHFFFAOYSA-N methyl 3-bromobenzoate Chemical compound COC(=O)C1=CC=CC(Br)=C1 KMFJVYMFCAIRAN-UHFFFAOYSA-N 0.000 description 1
- KQEVIFKPZOGBMZ-UHFFFAOYSA-N methyl 3-bromopropanoate Chemical compound COC(=O)CCBr KQEVIFKPZOGBMZ-UHFFFAOYSA-N 0.000 description 1
- CZNGTXVOZOWWKM-UHFFFAOYSA-N methyl 4-bromobenzoate Chemical compound COC(=O)C1=CC=C(Br)C=C1 CZNGTXVOZOWWKM-UHFFFAOYSA-N 0.000 description 1
- VHQJZYCGDGGQCN-UHFFFAOYSA-N methyl bromate Chemical compound COBr(=O)=O VHQJZYCGDGGQCN-UHFFFAOYSA-N 0.000 description 1
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- 150000002828 nitro derivatives Chemical class 0.000 description 1
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- 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000001993 wax Substances 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
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
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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
- C08F36/06—Butadiene
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- 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
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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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- 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
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—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
- C08F236/04—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
- C08F236/06—Butadiene
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- C08F2410/00—Features related to the catalyst preparation, the catalyst use or to the deactivation of the catalyst
- C08F2410/01—Additive used together with the catalyst, excluding compounds containing Al or B
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- C08F4/00—Polymerisation catalysts
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- C08F4/52—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 selected from boron, aluminium, gallium, indium, thallium or rare earths
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Abstract
Description
以下の一般式によって表わすことができるオリゴマー環式アルミノキサン
(式中、xは1〜約100、又は約10〜約50の範囲の整数であってもよく、yは2〜約100、又は約3〜約20の範囲の整数であってもよく、各Rは独立に、アルミニウム原子に炭素原子を介して結合される一価の有機基であってもよい)と、を含めることができる。一実施形態では、各Rは独立に、ヒドロカルビル基、例えば、限定するものではないが、アルキル基、シクロアルキル基、置換シクロアルキル基、アルケニル基、シクロアルケニル基、置換シクロアルケニル基、アリール基、置換アリール基、アラルキル基、アルカリル基、アリル基、及びアルキニル基であってもよく、各基は、1個の炭素原子(又は基を形成するのに適切な最小数の炭素原子)から最大で約20個の炭素原子を含有している。これらのヒドロカルビル基はまた、へテロ原子、例えば、限定するものではないが、窒素原子、酸素原子、ホウ素原子、ケイ素原子、硫黄原子、及びリン原子を含有していてもよい。なお、本出願で用いるアルミノキサンのモル数とは、オリゴマーアルミノキサン分子のモル数ではなく、アルミニウム原子のモル数を指すことに留意すべきである。この慣習は、アルミノキサンを用いる触媒系の技術分野において広く用いられている。
Si(OR1)xR2 4−x
式中、xは、1〜4の整数であり、各R1は、独立して、ヒドロカルビル基であり、各R2は、独立して、水素原子、ハロゲン原子、若しくは一価の有機基であり、又は、2つ以上のR2基が結合し、多価の有機基を形成してもよい。本明細書の目的において、多価の有機基は、二価、三価又は四価の有機基などの2つ以上の価数を有する有機基を指す。1つ以上の実施形態では、2つ以上のR2基が互いに結合するとき、形成されるヒドロカルビルオキシシラン化合物は、単環式、二環式、三環式、又は多環式であってよい。
200mL容の窒素をパージした乾燥容器に、40.7gの20.3%ヘキサン中ブタジエン溶液、7.7mLの0.50Mバーサチック酸ネオジム、19.3mLの未希釈トリイソブチルアルミニウム(3.96M)を加えた。混合物を30分間撹拌した後、5.6mLの1.02Mヘキサン中エチルアルミニウムジクロリドを加えた。次に、混合物を室温で熟成させ、予備形成した触媒溶液を形成した。触媒溶液のNd濃度は、0.041Mであった。
窒素をパージした6本の乾燥容器に、ヘキサン中のヘキサンと1,3−ブタジエンのブレンドを加え、300gの15.0%ヘキサン中ブタジエン溶液を得た。4本の容器に、0.65mLの1.18Mヘキサン中PhMe2SiOEt溶液、0.56mLの1.37Mヘキサン中Me3SiOCH2Ph溶液、0.49mLのヘキサン中1.56M Me3SiOPh溶液、及び0.67mLのヘキサン中1.18M Me3SiOEt溶液を、それぞれ投入した。続いて、1.88mLの予備形成した触媒溶液(1日熟成)を各容器に加えた後、0.00mL、0.28mL、0.28mL、0.28mL、0.28mL、及び0.28mLの1.09Mヘキサン中水素化ジ−イソブチルアルミニウムをそれぞれ加えた。容器を80℃の水浴内に置き、30分間混転した後、1.2mLの1.0Mトルエン中4,4’−ビス(ジエチルアミノ)ベンゾフェノンをポリマー溶液に加えた。これらの容器を80℃の水浴中に置き、更に約15分間混転した。得られたポリマーセメントを、2,6−ジ−tert−ブチル−4−メチルフェノールを含有する3mLのイソプロパノールでクエンチし、イソプロパノールで凝固させた。続いて、得られたポリマーを120℃のドラム乾燥器で乾燥し、これらの特性を表1にまとめた。
Claims (21)
- ポリジエンを製造するための方法であって、
ヒドロカルビルオキシシランの存在下でランタニドベース触媒系によって共役ジエンモノマーを重合する工程を含む、方法。 - 前記ランタニドベース触媒が、(a)ランタニド化合物、(b)アルキル化剤、及び(c)ハロゲン源の組み合わせ又はこれらの反応生成物である、請求項1に記載の方法。
- 前記アルキル化剤が、(i)式AlRnX3−nで定義される有機アルミニウム化合物であって、式中、各Rは、独立して、アルミニウム原子に炭素原子を介して結合される一価の有機基であり、各Xは、独立して、水素原子、ハロゲン原子、カルボキシレート基、アルコキシド基、又はアリールオキシド基であり、nは1〜3の範囲の整数である、有機アルミニウム化合物と、(ii)アルミノキサンと、の両方を含む、請求項2に記載の方法。
- 前記ヒドロカルビルオキシシラン化合物がアリル基を含まない、請求項1に記載の方法。
- 前記ヒドロカルビルオキシシラン化合物が、式Iで定義されてよく、
Si(OR1)xR2 4−x
式中、xは、1〜4の整数であり、各R1は、独立して、ヒドロカルビル基であり、各R2は、独立して、水素原子、ハロゲン原子、若しくは一価の有機基であり、又は、2つ以上のR2基が結合し、多価の有機基を形成してもよい、請求項1に記載の方法。 - 一価の有機基が、それぞれ独立して、アルキル、シクロアルキル、アリール、アラルキル、又はアルカリル基から選択される炭化水素基である、請求項5に記載の方法。
- 前記ヒドロカルビルオキシシラン化合物が、トリヒドロカルビルヒドロカルビルオキシシラン、ジヒドロカルビルジヒドロカルビルオキシシラン、及びヒドロカルビルトリヒドロカルビルオキシシランから選択される、請求項1に記載の方法。
- 前記ヒドロカルビルオキシシラン化合物が、トリアルキルアルキルオキシシラン、トリアルキルシクロアルキルオキシシラン、トリアルキルアリールオキシシラン、トリアルキルアラルキルオキシシラン、トリアルキルアルカリルオキシシラン、トリシクロアルキルアルキルオキシシラン、トリシクロアルキルシクロアルキルオキシシラン、トリシクロアルキルアリールオキシシラン、トリシクロアルキルアラルキルオキシシラン、トリシクロアルキルアルカリルオキシシラン、トリアリールアルキルオキシシラン、トリアリールシクロアルキルオキシシラン、トリアリールアリールオキシシラン、トリアリールアラルキルオキシシラン、トリアリールアルカリルオキシシラン、トリアラルキルアルキルオキシシラン、トリアラルキルシクロアルキルオキシシラン、トリアラルキルアリールオキシシラン、トリアラルキルアラルキルオキシシラン、トリアラルキルアルカリルオキシシラン、トリアルカリルアルキルオキシシラン、トリアルカリルシクロアルキルオキシシラン、トリアルカリルアリールオキシシラン、トリアルカリルアラルキルオキシシラン、トリアルカリルアルカリルオキシシラン、ジアルキルシクロアルキルアルキルオキシシラン、ジアルキルシクロアルキルシクロアルキルオキシシラン、ジアルキルシクロアルキルアリールオキシシラン、ジアルキルシクロアルキルアラルキルオキシシラン、ジアルキルシクロアルキルアルカリルオキシシラン、アルキルジシクロアルキルアルキルオキシシラン、アルキルジシクロアルキルシクロアルキルオキシシラン、アルキルジシクロアルキルアリールオキシシラン、アルキルジシクロアルキルアラルキルオキシシラン、アルキルジシクロアルキルアルカリルオキシシラン、ジアルキルアリールアルキルオキシシラン、ジアルキルアリールシクロアルキルオキシシラン、ジアルキルアリールアリールオキシシラン、ジアルキルアリールアラルキルオキシシラン、ジアルキルアリールアルカリルオキシシラン、アルキルジアリールアルキルオキシシラン、アルキルジアリールシクロアルキルオキシシラン、アルキルジアリールアリールオキシシラン、アルキルジアリールアラルキルオキシシラン、アルキルジアリールアルカリルオキシシラン、アルキルアリールシクロアルキルアルキルオキシシラン、アルキルアリールシクロアルキルシクロアルキルオキシシラン、アルキルアリールシクロアルキルアリールオキシシラン、アルキルアリールシクロアルキルアラルキルオキシシラン、及びアルキルアリールシクロアルキルアルカリルオキシシランから選択されるトリヒドロカルビルヒドロカルビルオキシシラン化合物である、請求項1に記載の方法。
- 前記ヒドロカルビルオキシシラン化合物が、ジアルキルジアルキルオキシシラン、ジアルキルジシクロアルキルオキシシラン、ジアルキルジアリールオキシシラン、ジアルキルジアラルキルオキシシラン、ジアルキルジアルカリルオキシシラン、ジアルキルアルキルオキシシクロアルキルオキシシラン、ジアルキルアルキルオキシアリールオキシシラン、ジアルキルアリールオキシシクロアルキルオキシシラン、ジシクロアルキルジアルキルオキシシラン、ジシクロアルキルジシクロアルキルオキシシラン、ジシクロアルキルジアリールオキシシラン、ジシクロアルキルジアラルキルオキシシラン、ジシクロアルキルジアルカリルオキシシラン、ジシクロアルキルアルキルオキシシクロアルキルオキシシラン、ジシクロアルキルアルキルオキシアリールオキシシラン、ジシクロアルキルアリールオキシシクロアルキルオキシシラン、ジアリールジアルキルオキシシラン、ジアリールジシクロアルキルオキシシラン、ジアリールジアリールオキシシラン、ジアリールジアラルキルオキシシラン、ジアリールジアルカリルオキシシラン、ジアリールアルキルオキシシクロアルキルオキシシラン、ジアリールアルキルオキシアリールオキシシラン、ジアリールアリールオキシシクロアルキルオキシシラン、ジアラルキルジアルキルオキシシラン、ジアラルキルジシクロアルキルオキシシラン、ジアラルキルジアリールオキシシラン、ジアラルキルジアラルキルオキシシラン、ジアラルキルジアルカリルオキシシラン、ジアラルキルアルキルオキシシクロアルキルオキシシラン、ジアラルキルアルキルオキシアリールオキシシラン、ジアラルキルアリールオキシシクロアルキルオキシシラン、ジアルカリルジアルキルオキシシラン、ジアルカリルジシクロアルキルオキシシラン、ジアルカリルジアリールオキシシラン、ジアルカリルジアラルキルオキシシラン、ジアルカリルジアルカリルオキシシラン、ジアルカリルアルキルオキシシクロアルキルオキシシラン、ジアルカリルアルキルオキシアリールオキシシラン、ジアルカリルアリールオキシシクロアルキルオキシシラン、アルキルシクロアルキルジアルキルオキシシラン、アルキルシクロアルキルジシクロアルキルオキシシラン、アルキルシクロアルキルジアリールオキシシラン、アルキルシクロアルキルジアラルキルオキシシラン、アルキルシクロアルキルジアルカリルオキシシラン、アルキルシクロアルキルアルキルオキシシクロアルキルオキシシラン、アルキルシクロアルキルアルキルオキシアリールオキシシラン、アルキルシクロアルキルアリールオキシシクロアルキルオキシシラン、アルキルアリールジアルキルオキシシラン、アルキルアリールジシクロアルキルオキシシラン、アルキルアリールジアリールオキシシラン、アルキルアリールジアラルキルオキシシラン、アルキルアリールジアルカリルオキシシラン、アルキルアリールアルキルオキシシクロアルキルオキシシラン、アルキルアリールアルキルオキシアリールオキシシラン、アルキルアリールアリールオキシシクロアルキルオキシシラン、アリールシクロアルキルジアルキルオキシシラン、アリールシクロアルキルジシクロアルキルオキシシラン、アリールシクロアルキルジアリールオキシシラン、アリールシクロアルキルジアラルキルオキシシラン、アリールシクロアルキルジアルカリルオキシシラン、アリールシクロアルキルアルキルオキシシクロアルキルオキシシラン、アリールシクロアルキルアルキルオキシアリールオキシシラン、及びアリールシクロアルキルアリールオキシシクロアルキルオキシシランから選択されるジヒドロカルビルジヒドロカルビルオキシシラン化合物である、請求項1に記載の方法。
- 前記ヒドロカルビルオキシシラン化合物が、アルキルトリアルキルオキシシラン、アルキルトリシクロアルキルオキシシラン、アルキルトリアリールオキシシラン、アルキルトリアラルキルオキシシラン、アルキルトリアルカリルオキシシラン、アルキルジアルキルオキシシクロアルキルオキシシラン、アルキルアルキルオキシジシクロアルキルオキシシラン、アルキルジアルキルオキシアリールオキシシラン、アルキルアルキルオキシジアリールオキシシラン、アルキルアルキルオキシアリールオキシシクロアルキルオキシシラン、シクロアルキルトリアルキルオキシシラン、シクロアルキルトリシクロアルキルオキシシラン、シクロアルキルトリアリールオキシシラン、シクロアルキルトリアラルキルオキシシラン、シクロアルキルトリアルカリルオキシシラン、シクロアルキルジアルキルオキシシクロアルキルオキシシラン、シクロアルキルアルキルオキシジシクロアルキルオキシシラン、シクロアルキルジアルキルオキシアリールオキシシラン、シクロアルキルアルキルオキシジアリールオキシシラン、シクロアルキルアルキルオキシアリールオキシシクロアルキルオキシシラン、アリールトリアルキルオキシシラン、アリールトリシクロアルキルオキシシラン、アリールトリアリールオキシシラン、アリールトリアラルキルオキシシラン、アリールトリアルカリルオキシシラン、アリールジアルキルオキシシクロアルキルオキシシラン、アリールアルキルオキシジシクロアルキルオキシシラン、アリールジアルキルオキシアリールオキシシラン、アリールアルキルオキシジアリールオキシシラン、アリールアルキルオキシアリールオキシシクロアルキルオキシシラン、アラルキルトリアルキルオキシシラン、アラルキルトリシクロアルキルオキシシラン、アラルキルトリアリールオキシシラン、アラルキルトリアラルキルオキシシラン、アラルキルトリアルカリルオキシシラン、アラルキルジアルキルオキシシクロアルキルオキシシラン、アラルキルアルキルオキシジシクロアルキルオキシシラン、アラルキルジアルキルオキシアリールオキシシラン、アラルキルアルキルオキシジアリールオキシシラン、アラルキルアルキルオキシアリールオキシシクロアルキルオキシシラン、アルカリルトリアルキルオキシシラン、アルカリルトリシクロアルキルオキシシラン、アルカリルトリアリールオキシシラン、アルカリルトリアラルキルオキシシラン、アルカリルトリアルカリルオキシシラン、アルカリルジアルキルオキシシクロアルキルオキシシラン、アルカリルアルキルオキシジシクロアルキルオキシシラン、アルカリルジアルキルオキシアリールオキシシラン、アルカリルアルキルオキシジアリールオキシシラン、及びアルカリルアルキルオキシアリールオキシシクロアルキルオキシシランから選択されるヒドロカルビルトリヒドロカルビルオキシシラン化合物である、請求項1に記載の方法。
- 前記ヒドロカルビルオキシシラン化合物が、トリメチルメトキシシラン、トリメチルエトキシシラン、トリメチルフェノキシシラン、トリエチルメトキシシラン、トリエチルエトキシシラン、トリエチルフェノキシシラン、トリ−n−プロピルメトキシシラン、トリ−n−プロピルエトキシシラン、トリ−n−プロピルフェノキシシラン、トリイソプロピルメトキシシラン、トリイソプロピルエトキシシラン、トリイソプロピルフェノキシシラン、トリ−n−ブチルメトキシシラン、トリ−n−ブチルエトキシシラン、トリ−n−ブチルフェノキシシラン、トリ−t−ブチルメトキシシラン、トリ−t−ブチルエトキシシラン、トリ−t−ブチルフェノキシシラン、トリネオペンチルメトキシシラン、トリネオペンチルエトキシシラン、トリネオペンチルフェノキシシラン、トリ−n−ペンチルメトキシシラン、トリ−n−ペンチルエトキシシラン、トリ−n−ペンチルフェノキシシラン、トリ−n−ヘキシルメトキシシラン、トリ−n−ヘキシルエトキシシラン、トリ−n−ヘキシルフェノキシシラン、トリベンジルメトキシシラン、トリベンジルエトキシシラン、トリベンジルフェノキシシラン、トリシクロヘキシルメトキシシラン、トリシクロヘキシルエトキシシラン、トリシクロヘキシルフェノキシシラン、トリフェニルメトキシシラン、トリフェニルエトキシシラン、トリフェニルフェノキシシラン、ジメチルエチルメトキシシラン、ジメチルエチルエトキシシラン、ジメチルエチルフェノキシシラン、ジメチルイソプロピルメトキシシラン、ジメチルイソプロピルエトキシシラン、ジメチルイソプロピルフェノキシシラン、ジメチルフェニルメトキシシラン、ジメチルフェニルエトキシシラン、ジメチルフェニルフェノキシシラン、エチルジフェニルメトキシシラン、エチルジフェニルエトキシシラン、エチルジフェニルフェノキシシラン、イソプロピルジフェニルメトキシシラン、イソプロピルジフェニルエトキシシラン、イソプロピルジフェニルフェノキシシラン、イソプロピルジエチルメトキシシラン、イソプロピルジエチルエトキシシラン、イソプロピルジエチルフェノキシシラン、ジメチルシクロヘキシルメトキシシラン、ジメチルシクロヘキシルエトキシシラン、ジメチルシクロヘキシルフェノキシシラン、ジエチルシクロヘキシルメトキシシラン、ジエチルシクロヘキシルエトキシシラン、及びジエチルシクロヘキシルフェノキシシランから選択されるトリヒドロカルビルヒドロカルビルオキシシラン化合物である、請求項1に記載の方法。
- 前記ヒドロカルビルオキシシラン化合物が、ジメチルジメトキシシラン、ジメチルジエトキシシラン、ジメチルジフェノキシシラン、ジメチルメトキシエトキシシラン、ジメチルメトキシフェノキシシラン、ジメチルフェノキシエトキシシラン、ジエチルジメトキシシラン、ジエチルジエトキシシラン、ジエチルジフェノキシシラン、ジエチルメトキシエトキシシラン、ジエチルメトキシフェノキシシラン、ジエチルフェノキシエトキシシラン、ジ−n−プロピルジメトキシシラン、ジ−n−プロピルジエトキシシラン、ジ−n−プロピルジフェノキシシラン、ジ−n−プロピルメトキシエトキシシラン、ジ−n−プロピルメトキシフェノキシシラン、ジ−n−プロピルフェノキシエトキシシラン、ジイソプロピルジメトキシシラン、ジイソプロピルジエトキシシラン、ジイソプロピルジフェノキシシラン、ジイソプロピルメトキシエトキシシラン、ジイソプロピルメトキシフェノキシシラン、ジイソプロピルフェノキシエトキシシラン、ジ−n−ブチルジメトキシシラン、ジ−n−ブチルジエトキシシラン、ジ−n−ブチルジフェノキシシラン、ジ−n−ブチルメトキシエトキシシラン、ジ−n−ブチルメトキシフェノキシシラン、ジ−n−ブチルフェノキシエトキシシラン、ジ−t−ブチルジメトキシシラン、ジ−t−ブチルジエトキシシラン、ジ−t−ブチルジフェノキシシラン、ジ−t−ブチルメトキシエトキシシラン、ジ−t−ブチルメトキシフェノキシシラン、ジ−t−ブチルフェノキシエトキシシラン、ジネオペンチルジメトキシシラン、ジネオペンチルジエトキシシラン、ジネオペンチルジフェノキシシラン、ジネオペンチルメトキシエトキシシラン、ジネオペンチルメトキシフェノキシシラン、ジネオペンチルフェノキシエトキシシラン、ジ−n−ペンチルジメトキシシラン、ジ−n−ペンチルジエトキシシラン、ジ−n−ペンチルジフェノキシシラン、ジ−n−ペンチルメトキシエトキシシラン、ジ−n−ペンチルメトキシフェノキシシラン、ジ−n−ペンチルフェノキシエトキシシラン、ジ−n−ヘキシルジメトキシシラン、ジ−n−ヘキシルジエトキシシラン、ジ−n−ヘキシルジフェノキシシラン、ジ−n−ヘキシルメトキシエトキシシラン、ジ−n−ヘキシルメトキシフェノキシシラン、ジ−n−ヘキシルフェノキシエトキシシラン、ジベンジルジメトキシシラン、ジベンジルジエトキシシラン、ジベンジルジフェノキシシラン、ジベンジルメトキシエトキシシラン、ジベンジルメトキシフェノキシシラン、ジベンジルフェノキシエトキシシラン、ジフェニルジメトキシシラン、ジフェニルジエトキシシラン、ジフェニルジフェノキシシラン、ジフェニルメトキシエトキシシラン、ジフェニルメトキシフェノキシシラン、ジフェニルフェノキシエトキシシラン、ジシクロヘキシルジメトキシシラン、ジシクロヘキシルジエトキシシラン、ジシクロヘキシルジフェノキシシラン、ジシクロヘキシルメトキシエトキシシラン、ジシクロヘキシルメトキシフェノキシシラン、ジシクロヘキシルフェノキシエトキシシラン、メチルエチルジメトキシシラン、メチルエチルジエトキシシラン、メチルエチルジフェノキシシラン、メチルエチルメトキシエトキシシラン、メチルエチルメトキシフェノキシシラン、メチルエチルフェノキシエトキシシラン、メチルイソプロピルジメトキシシラン、メチルイソプロピルジエトキシシラン、メチルイソプロピルジフェノキシシラン、メチルイソプロピルメトキシエトキシシラン、メチルイソプロピルメトキシフェノキシシラン、メチルイソプロピルフェノキシエトキシシラン、メチルフェニルジメトキシシラン、メチルフェニルジエトキシシラン、メチルフェニルジフェノキシシラン、メチルフェニルメトキシエトキシシラン、メチルフェニルメトキシフェノキシシラン、メチルフェニルフェノキシエトキシシラン、エチルフェニルジメトキシシラン、エチルフェニルジエトキシシラン、エチルフェニルジフェノキシシラン、エチルフェニルメトキシエトキシシラン、エチルフェニルメトキシフェノキシシラン、エチルフェニルフェノキシエトキシシラン、イソプロピルフェニルジメトキシシラン、イソプロピルフェニルジエトキシシラン、イソプロピルフェニルジフェノキシシラン、イソプロピルフェニルメトキシエトキシシラン、イソプロピルフェニルメトキシフェノキシシラン、イソプロピルフェニルフェノキシエトキシシラン、イソプロピルエチルジメトキシシラン、イソプロピルエチルジエトキシシラン、イソプロピルエチルジフェノキシシラン、イソプロピルエチルメトキシエトキシシラン、イソプロピルエチルメトキシフェノキシシラン、イソプロピルエチルフェノキシエトキシシラン、メチルシクロヘキシルジメトキシシラン、メチルシクロヘキシルジエトキシシラン、メチルシクロヘキシルジフェノキシシラン、メチルシクロヘキシルメトキシエトキシシラン、メチルシクロヘキシルメトキシフェノキシシラン、メチルシクロヘキシルフェノキシエトキシシラン、エチルシクロヘキシルジメトキシシラン、エチルシクロヘキシルジエトキシシラン、エチルシクロヘキシルジフェノキシシラン、エチルシクロヘキシルメトキシエトキシシラン、エチルシクロヘキシルメトキシフェノキシシラン、及びエチルシクロヘキシルフェノキシエトキシシランから選択されるジヒドロカルビルジヒドロカルビルオキシシラン化合物である、請求項1に記載の方法。
- 前記ヒドロカルビルオキシシラン化合物が、メチルトリメトキシシラン、メチルトリエトキシシラン、メチルトリフェノキシシラン、メチルジメトキシエトキシシラン、メチルジメトキシフェノキシシラン、メチルジフェノキシエトキシシラン、メチルメトキシエトキシフェノキシシラン、エチルトリメトキシシラン、エチルトリエトキシシラン、エチルトリフェノキシシラン、エチルジメトキシエトキシシラン、エチルジメトキシフェノキシシラン、エチルジフェノキシエトキシシラン、エチルメトキシエトキシフェノキシシラン、n−プロピルトリメトキシシラン、n−プロピルトリエトキシシラン、n−プロピルトリフェノキシシラン、n−プロピルジメトキシエトキシシラン、n−プロピルジメトキシフェノキシシラン、n−プロピルジフェノキシエトキシシラン、n−プロピルメトキシエトキシフェノキシシラン、イソプロピルトリメトキシシラン、イソプロピルトリエトキシシラン、イソプロピルトリフェノキシシラン、イソプロピルジメトキシエトキシシラン、イソプロピルジメトキシフェノキシシラン、イソプロピルジフェノキシエトキシシラン、イソプロピルメトキシエトキシフェノキシシラン、n−ブチルトリメトキシシラン、n−ブチルトリエトキシシラン、n−ブチルトリフェノキシシラン、n−ブチルジメトキシエトキシシラン、n−ブチルジメトキシフェノキシシラン、n−ブチルジフェノキシエトキシシラン、n−ブチルメトキシエトキシフェノキシシラン、t−ブチルトリメトキシシラン、t−ブチルトリエトキシシラン、t−ブチルトリフェノキシシラン、t−ブチルジメトキシエトキシシラン、t−ブチルジメトキシフェノキシシラン、t−ブチルジフェノキシエトキシシラン、t−ブチルメトキシエトキシフェノキシシラン、ネオペンチルトリメトキシシラン、ネオペンチルトリエトキシシラン、ネオペンチルトリフェノキシシラン、ネオペンチルジメトキシエトキシシラン、ネオペンチルジメトキシフェノキシシラン、ネオペンチルジフェノキシエトキシシラン、ネオペンチルメトキシエトキシフェノキシシラン、n−ペンチルトリメトキシシラン、n−ペンチルトリエトキシシラン、n−ペンチルトリフェノキシシラン、n−ペンチルジメトキシエトキシシラン、n−ペンチルジメトキシフェノキシシラン、n−ペンチルジフェノキシエトキシシラン、n−ペンチルメトキシエトキシフェノキシシラン、n−ヘキシルトリメトキシシラン、n−ヘキシルトリエトキシシラン、n−ヘキシルトリフェノキシシラン、n−ヘキシルジメトキシエトキシシラン、n−ヘキシルジメトキシフェノキシシラン、n−ヘキシルジフェノキシエトキシシラン、n−ヘキシルメトキシエトキシフェノキシシラン、ベンジルトリメトキシシラン、ベンジルトリエトキシシラン、ベンジルトリフェノキシシラン、ベンジルジメトキシエトキシシラン、ベンジルジメトキシフェノキシシラン、ベンジルジフェノキシエトキシシラン、ベンジルメトキシエトキシフェノキシシラン、フェニルトリメトキシシラン、フェニルトリエトキシシラン、フェニルトリフェノキシシラン、フェニルジメトキシエトキシシラン、フェニルジメトキシフェノキシシラン、フェニルジフェノキシエトキシシラン、フェニルメトキシエトキシフェノキシシラン、シクロヘキシルトリメトキシシラン、シクロヘキシルトリエトキシシラン、シクロヘキシルトリフェノキシシラン、シクロヘキシルジメトキシエトキシシラン、シクロヘキシルジメトキシフェノキシシラン、シクロヘキシルジフェノキシエトキシシラン、及びシクロヘキシルメトキシエトキシフェノキシシランから選択されるヒドロカルビルトリヒドロカルビルオキシシラン化合物である、請求項1に記載の方法。
- ポリジエンを製造するための方法であって、
(i)ランタニド含有化合物、アルキル化剤、及びハロゲン源を組み合わせることによって活性触媒を形成する工程と、
(ii)前記活性触媒及びヒドロカルビルオキシシラン化合物の存在下で共役ジエンモノマーを重合する工程と、を含む、方法。 - 前記活性触媒が予備形成されている、請求項14に記載の方法。
- 前記重合工程が、重合混合物の総重量に基づいて20重量%未満の有機溶媒を含む前記重合混合物中で行われる、請求項14に記載の方法。
- 前記重合工程が、反応性鎖末端を有するポリジエンを生成し、官能化剤を前記反応性鎖末端と反応させる工程を更に含む、請求項14に記載の方法。
- 前記重合工程の前に、前記ヒドロカルビルオキシシラン化合物を前記活性触媒に導入する工程を更に含む、請求項14に記載の方法。
- 前記ヒドロカルビルオキシシラン化合物を前記共役ジエンモノマーに、直接かつ個々に導入する工程を更に含む、請求項14に記載の方法。
- 前記ヒドロカルビルオキシシラン化合物を前記共役ジエンモノマーに、5%の前記モノマーが重合される前に導入する、請求項19に記載の方法。
- 前記活性触媒がモノマーの存在下で予備形成されている、請求項15に記載の方法。
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JP6811841B2 (ja) | 2021-01-13 |
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