JP2010506002A - 分岐重合体、並びにその合成方法及び使用方法 - Google Patents
分岐重合体、並びにその合成方法及び使用方法 Download PDFInfo
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- JP2010506002A JP2010506002A JP2009531480A JP2009531480A JP2010506002A JP 2010506002 A JP2010506002 A JP 2010506002A JP 2009531480 A JP2009531480 A JP 2009531480A JP 2009531480 A JP2009531480 A JP 2009531480A JP 2010506002 A JP2010506002 A JP 2010506002A
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- Prior art keywords
- polymer
- nickel
- skeleton
- neodymium
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- NTIWOYZPHSWEAP-UHFFFAOYSA-M (4-methylphenyl)-(2-methylpropyl)alumanylium;chloride Chemical compound [Cl-].CC(C)C[Al+]C1=CC=C(C)C=C1 NTIWOYZPHSWEAP-UHFFFAOYSA-M 0.000 description 1
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- FCULJJOWPNXTTG-UHFFFAOYSA-L dipentyl phosphate;nickel(2+) Chemical compound [Ni+2].CCCCCOP([O-])(=O)OCCCCC.CCCCCOP([O-])(=O)OCCCCC FCULJJOWPNXTTG-UHFFFAOYSA-L 0.000 description 1
- BUHQQXGTFKPOJT-UHFFFAOYSA-K diphenyl phosphate;neodymium(3+) Chemical compound [Nd+3].C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1.C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1.C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 BUHQQXGTFKPOJT-UHFFFAOYSA-K 0.000 description 1
- RIARDECMAOPYBG-UHFFFAOYSA-L diphenyl phosphate;nickel(2+) Chemical compound [Ni+2].C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1.C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 RIARDECMAOPYBG-UHFFFAOYSA-L 0.000 description 1
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- FNFSVRHAXXUJAX-UHFFFAOYSA-L diphenylphosphinate;nickel(2+) Chemical compound [Ni+2].C=1C=CC=CC=1P(=O)([O-])C1=CC=CC=C1.C=1C=CC=CC=1P(=O)([O-])C1=CC=CC=C1 FNFSVRHAXXUJAX-UHFFFAOYSA-L 0.000 description 1
- XOCWTYIVWYOSGQ-UHFFFAOYSA-N dipropylalumane Chemical compound C(CC)[AlH]CCC XOCWTYIVWYOSGQ-UHFFFAOYSA-N 0.000 description 1
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- 238000007306 functionalization reaction Methods 0.000 description 1
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- WXXZSFJVAMRMPV-UHFFFAOYSA-K gallium(iii) fluoride Chemical compound F[Ga](F)F WXXZSFJVAMRMPV-UHFFFAOYSA-K 0.000 description 1
- DWRNSCDYNYYYHT-UHFFFAOYSA-K gallium(iii) iodide Chemical compound I[Ga](I)I DWRNSCDYNYYYHT-UHFFFAOYSA-K 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
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- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
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- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
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- 230000000977 initiatory effect Effects 0.000 description 1
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- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 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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- 125000000468 ketone group Chemical group 0.000 description 1
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- 239000007791 liquid phase Substances 0.000 description 1
- OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- 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
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- LZFCBBSYZJPPIV-UHFFFAOYSA-M magnesium;hexane;bromide Chemical compound [Mg+2].[Br-].CCCCC[CH2-] LZFCBBSYZJPPIV-UHFFFAOYSA-M 0.000 description 1
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- QGEFGPVWRJCFQP-UHFFFAOYSA-M magnesium;methanidylbenzene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C1=CC=CC=C1 QGEFGPVWRJCFQP-UHFFFAOYSA-M 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
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- UEBCFKSPKUURKQ-UHFFFAOYSA-L methylaluminum(2+);difluoride Chemical compound [F-].[F-].[Al+2]C UEBCFKSPKUURKQ-UHFFFAOYSA-L 0.000 description 1
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- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
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- 238000010068 moulding (rubber) Methods 0.000 description 1
- SQUOJZZETZQEOF-UHFFFAOYSA-K n,n-di(propan-2-yl)carbamodithioate;neodymium(3+) Chemical compound [Nd+3].CC(C)N(C(C)C)C([S-])=S.CC(C)N(C(C)C)C([S-])=S.CC(C)N(C(C)C)C([S-])=S SQUOJZZETZQEOF-UHFFFAOYSA-K 0.000 description 1
- PYLMYJVNPREXPE-UHFFFAOYSA-L n,n-di(propan-2-yl)carbamodithioate;nickel(2+) Chemical compound [Ni+2].CC(C)N(C(C)C)C([S-])=S.CC(C)N(C(C)C)C([S-])=S PYLMYJVNPREXPE-UHFFFAOYSA-L 0.000 description 1
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- ZVFKOPAELLPDTR-UHFFFAOYSA-L n,n-dibenzylcarbamodithioate;nickel(2+) Chemical compound [Ni+2].C=1C=CC=CC=1CN(C(=S)[S-])CC1=CC=CC=C1.C=1C=CC=CC=1CN(C(=S)[S-])CC1=CC=CC=C1 ZVFKOPAELLPDTR-UHFFFAOYSA-L 0.000 description 1
- UKJJHVZVXZCPRF-UHFFFAOYSA-K n,n-dibutylcarbamodithioate;neodymium(3+) Chemical compound [Nd+3].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC UKJJHVZVXZCPRF-UHFFFAOYSA-K 0.000 description 1
- SZBUPRSARRAZQN-UHFFFAOYSA-K n,n-diethylcarbamodithioate;neodymium(3+) Chemical compound [Nd+3].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S.CCN(CC)C([S-])=S SZBUPRSARRAZQN-UHFFFAOYSA-K 0.000 description 1
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- IQILFJXGSRKIIW-UHFFFAOYSA-N neodymium(3+) triazide Chemical compound [Nd+3].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-] IQILFJXGSRKIIW-UHFFFAOYSA-N 0.000 description 1
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- FJWHSHNHTPHETF-UHFFFAOYSA-N neodymium(3+) tricyanide Chemical compound [Nd+3].[C-]#N.[C-]#N.[C-]#N FJWHSHNHTPHETF-UHFFFAOYSA-N 0.000 description 1
- HCOLBMWNEVUKDB-UHFFFAOYSA-K neodymium(3+) trithiocyanate Chemical compound [Nd+3].[S-]C#N.[S-]C#N.[S-]C#N HCOLBMWNEVUKDB-UHFFFAOYSA-K 0.000 description 1
- MPKWOMQKNIDCKY-UHFFFAOYSA-K neodymium(3+);2-nonylphenolate Chemical compound [Nd+3].CCCCCCCCCC1=CC=CC=C1[O-].CCCCCCCCCC1=CC=CC=C1[O-].CCCCCCCCCC1=CC=CC=C1[O-] MPKWOMQKNIDCKY-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
- HZHUIQPXRWTHNF-UHFFFAOYSA-N neodymium(3+);propan-2-olate Chemical compound [Nd+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] HZHUIQPXRWTHNF-UHFFFAOYSA-N 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
- LBWLQVSRPJHLEY-UHFFFAOYSA-K neodymium(3+);tribromide Chemical compound Br[Nd](Br)Br LBWLQVSRPJHLEY-UHFFFAOYSA-K 0.000 description 1
- SXSPKVLHGFYNGI-UHFFFAOYSA-K neodymium(3+);tricarbamodithioate Chemical class [Nd+3].NC([S-])=S.NC([S-])=S.NC([S-])=S SXSPKVLHGFYNGI-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
- DKSXWSAKLYQPQE-UHFFFAOYSA-K neodymium(3+);triiodide Chemical compound I[Nd](I)I DKSXWSAKLYQPQE-UHFFFAOYSA-K 0.000 description 1
- TZNZEEADHYGQQO-UHFFFAOYSA-K neodymium(3+);triphenoxide Chemical compound [Nd+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 TZNZEEADHYGQQO-UHFFFAOYSA-K 0.000 description 1
- ATINCSYRHURBSP-UHFFFAOYSA-K neodymium(iii) chloride Chemical compound Cl[Nd](Cl)Cl ATINCSYRHURBSP-UHFFFAOYSA-K 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002815 nickel Chemical group 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 229940116232 nickel gluconate Drugs 0.000 description 1
- MLAOBUNVZFBLLT-UHFFFAOYSA-N nickel propan-2-ol Chemical compound [Ni].CC(C)O.CC(C)O MLAOBUNVZFBLLT-UHFFFAOYSA-N 0.000 description 1
- JRUBGUVYQMKOMK-UHFFFAOYSA-N nickel(2+) diazide Chemical compound [Ni+2].[N-]=[N+]=[N-].[N-]=[N+]=[N-] JRUBGUVYQMKOMK-UHFFFAOYSA-N 0.000 description 1
- DVQYNXRSNFYQRW-IYEMJOQQSA-L nickel(2+);(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanoate Chemical compound [Ni+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O DVQYNXRSNFYQRW-IYEMJOQQSA-L 0.000 description 1
- SXWNIROSIVQDIZ-UHFFFAOYSA-L nickel(2+);(4-nonylphenyl)-dioxido-oxo-$l^{5}-phosphane Chemical compound [Ni+2].CCCCCCCCCC1=CC=C(P([O-])([O-])=O)C=C1 SXWNIROSIVQDIZ-UHFFFAOYSA-L 0.000 description 1
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 1
- LVBIMKHYBUACBU-CVBJKYQLSA-L nickel(2+);(z)-octadec-9-enoate Chemical compound [Ni+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O LVBIMKHYBUACBU-CVBJKYQLSA-L 0.000 description 1
- FPOBXNYAWLLCGZ-UHFFFAOYSA-N nickel(2+);1,2,3,4,5-pentamethylcyclopenta-1,3-diene Chemical compound [Ni+2].CC=1C(C)=C(C)[C-](C)C=1C.CC=1C(C)=C(C)[C-](C)C=1C FPOBXNYAWLLCGZ-UHFFFAOYSA-N 0.000 description 1
- CHPLEWYRKUFKQP-UHFFFAOYSA-N nickel(2+);1,2,3,5,5-pentamethylcyclopenta-1,3-diene Chemical compound [Ni+2].CC1=[C-]C(C)(C)C(C)=C1C.CC1=[C-]C(C)(C)C(C)=C1C CHPLEWYRKUFKQP-UHFFFAOYSA-N 0.000 description 1
- IFVKQLYUZCWJSI-UHFFFAOYSA-L nickel(2+);2-nonylphenolate Chemical compound [Ni+2].CCCCCCCCCC1=CC=CC=C1[O-].CCCCCCCCCC1=CC=CC=C1[O-] IFVKQLYUZCWJSI-UHFFFAOYSA-L 0.000 description 1
- WTNNDNBKPMUIQG-UHFFFAOYSA-N nickel(2+);5-propan-2-ylcyclopenta-1,3-diene Chemical compound [Ni+2].CC(C)[C-]1C=CC=C1.CC(C)[C-]1C=CC=C1 WTNNDNBKPMUIQG-UHFFFAOYSA-N 0.000 description 1
- GAIQJSWQJOZOMI-UHFFFAOYSA-L nickel(2+);dibenzoate Chemical compound [Ni+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 GAIQJSWQJOZOMI-UHFFFAOYSA-L 0.000 description 1
- IPLJNQFXJUCRNH-UHFFFAOYSA-L nickel(2+);dibromide Chemical compound [Ni+2].[Br-].[Br-] IPLJNQFXJUCRNH-UHFFFAOYSA-L 0.000 description 1
- UJZUVEGMICTCJB-UHFFFAOYSA-L nickel(2+);dicyanate Chemical compound N#CO[Ni]OC#N UJZUVEGMICTCJB-UHFFFAOYSA-L 0.000 description 1
- NLEUXPOVZGDKJI-UHFFFAOYSA-N nickel(2+);dicyanide Chemical compound [Ni+2].N#[C-].N#[C-] NLEUXPOVZGDKJI-UHFFFAOYSA-N 0.000 description 1
- HZPNKQREYVVATQ-UHFFFAOYSA-L nickel(2+);diformate Chemical compound [Ni+2].[O-]C=O.[O-]C=O HZPNKQREYVVATQ-UHFFFAOYSA-L 0.000 description 1
- QTOJRHLRJFVPJN-UHFFFAOYSA-L nickel(2+);diphenoxide Chemical compound C=1C=CC=CC=1O[Ni]OC1=CC=CC=C1 QTOJRHLRJFVPJN-UHFFFAOYSA-L 0.000 description 1
- ALYMILAYQDOMFU-UHFFFAOYSA-L nickel(2+);dithiocyanate Chemical compound [Ni+2].[S-]C#N.[S-]C#N ALYMILAYQDOMFU-UHFFFAOYSA-L 0.000 description 1
- JMWUYEFBFUCSAK-UHFFFAOYSA-L nickel(2+);octadecanoate Chemical compound [Ni+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O JMWUYEFBFUCSAK-UHFFFAOYSA-L 0.000 description 1
- DOLZKNFSRCEOFV-UHFFFAOYSA-L nickel(2+);oxalate Chemical compound [Ni+2].[O-]C(=O)C([O-])=O DOLZKNFSRCEOFV-UHFFFAOYSA-L 0.000 description 1
- XNTIUKWGWWSKLH-UHFFFAOYSA-L nickel(2+);pentanoate Chemical compound [Ni+2].CCCCC([O-])=O.CCCCC([O-])=O XNTIUKWGWWSKLH-UHFFFAOYSA-L 0.000 description 1
- QFVGCVZHAQQIMT-UHFFFAOYSA-L nickel(2+);prop-2-enoate Chemical compound [Ni+2].[O-]C(=O)C=C.[O-]C(=O)C=C QFVGCVZHAQQIMT-UHFFFAOYSA-L 0.000 description 1
- JFNOTRAFTNLNOK-UHFFFAOYSA-L nickel(2+);pyridine-2-carboxylate Chemical compound [Ni+2].[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1 JFNOTRAFTNLNOK-UHFFFAOYSA-L 0.000 description 1
- DBJLJFTWODWSOF-UHFFFAOYSA-L nickel(ii) fluoride Chemical compound F[Ni]F DBJLJFTWODWSOF-UHFFFAOYSA-L 0.000 description 1
- BFSQJYRFLQUZKX-UHFFFAOYSA-L nickel(ii) iodide Chemical compound I[Ni]I BFSQJYRFLQUZKX-UHFFFAOYSA-L 0.000 description 1
- JUJLDYVCLNLGTH-UHFFFAOYSA-N nickel;1,2,3,4-tetramethylcyclopentane Chemical compound [Ni].C[C]1[CH][C](C)[C](C)[C]1C.C[C]1[CH][C](C)[C](C)[C]1C JUJLDYVCLNLGTH-UHFFFAOYSA-N 0.000 description 1
- MLAAJSDYNMCCHJ-UHFFFAOYSA-N nickel;1-pentoxyphosphonoyloxypentane Chemical compound [Ni].CCCCCOP(=O)OCCCCC MLAAJSDYNMCCHJ-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- ZWWQICJTBOCQLA-UHFFFAOYSA-N o-propan-2-yl (propan-2-yloxycarbothioyldisulfanyl)methanethioate Chemical compound CC(C)OC(=S)SSC(=S)OC(C)C ZWWQICJTBOCQLA-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000005474 octanoate group Chemical group 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
- KMKBWZXSKDYZDZ-UHFFFAOYSA-M octyl(phenyl)alumanylium;chloride Chemical compound [Cl-].CCCCCCCC[Al+]C1=CC=CC=C1 KMKBWZXSKDYZDZ-UHFFFAOYSA-M 0.000 description 1
- SOEVKJXMZBAALG-UHFFFAOYSA-N octylalumane Chemical compound CCCCCCCC[AlH2] SOEVKJXMZBAALG-UHFFFAOYSA-N 0.000 description 1
- RBLGTYCOUOIUNY-UHFFFAOYSA-L octylaluminum(2+);dichloride Chemical compound CCCCCCCC[Al](Cl)Cl RBLGTYCOUOIUNY-UHFFFAOYSA-L 0.000 description 1
- CBFCDTFDPHXCNY-UHFFFAOYSA-N octyldodecane Natural products CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 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
- CUIJJJLOSZSJRO-UHFFFAOYSA-M phenyl(propan-2-yl)alumanylium;chloride Chemical compound [Cl-].CC(C)[Al+]C1=CC=CC=C1 CUIJJJLOSZSJRO-UHFFFAOYSA-M 0.000 description 1
- ZKGDHJAHOGRQEP-UHFFFAOYSA-N phenyl(propyl)alumane Chemical compound C1(=CC=CC=C1)[AlH]CCC ZKGDHJAHOGRQEP-UHFFFAOYSA-N 0.000 description 1
- AAQNAPUTWYBWOV-UHFFFAOYSA-M phenyl(propyl)alumanylium;chloride Chemical compound [Cl-].CCC[Al+]C1=CC=CC=C1 AAQNAPUTWYBWOV-UHFFFAOYSA-M 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000005054 phenyltrichlorosilane Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
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- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-M pivalate Chemical compound CC(C)(C)C([O-])=O IUGYQRQAERSCNH-UHFFFAOYSA-M 0.000 description 1
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- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
- 238000012673 precipitation polymerization Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
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- 239000001294 propane Substances 0.000 description 1
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- 230000001681 protective effect Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
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- 239000004576 sand Substances 0.000 description 1
- VTQZBGAODFEJOW-UHFFFAOYSA-N selenium tetrabromide Chemical compound Br[Se](Br)(Br)Br VTQZBGAODFEJOW-UHFFFAOYSA-N 0.000 description 1
- LNBXMNQCXXEHFT-UHFFFAOYSA-N selenium tetrachloride Chemical compound Cl[Se](Cl)(Cl)Cl LNBXMNQCXXEHFT-UHFFFAOYSA-N 0.000 description 1
- AIFMYMZGQVTROK-UHFFFAOYSA-N silicon tetrabromide Chemical compound Br[Si](Br)(Br)Br AIFMYMZGQVTROK-UHFFFAOYSA-N 0.000 description 1
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- 238000006467 substitution reaction Methods 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
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- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 1
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- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
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- 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
- JKNHZOAONLKYQL-UHFFFAOYSA-K tribromoindigane Chemical compound Br[In](Br)Br JKNHZOAONLKYQL-UHFFFAOYSA-K 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
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- FVRKTAOFDKFAMI-UHFFFAOYSA-M tributylstannanylium;bromide Chemical compound [Br-].CCCC[Sn+](CCCC)CCCC FVRKTAOFDKFAMI-UHFFFAOYSA-M 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
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-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
- KQPIFPBKXYBDGV-UHFFFAOYSA-M triethylstannanylium;bromide Chemical compound CC[Sn](Br)(CC)CC KQPIFPBKXYBDGV-UHFFFAOYSA-M 0.000 description 1
- JNLSTWIBJFIVHZ-UHFFFAOYSA-K trifluoroindigane Chemical compound F[In](F)F JNLSTWIBJFIVHZ-UHFFFAOYSA-K 0.000 description 1
- XRADHEAKQRNYQQ-UHFFFAOYSA-K trifluoroneodymium Chemical compound F[Nd](F)F XRADHEAKQRNYQQ-UHFFFAOYSA-K 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- RMUKCGUDVKEQPL-UHFFFAOYSA-K triiodoindigane Chemical compound I[In](I)I RMUKCGUDVKEQPL-UHFFFAOYSA-K 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
- MZGUIAFRJWSYJJ-UHFFFAOYSA-M trimethylstannanylium;bromide Chemical compound C[Sn](C)(C)Br MZGUIAFRJWSYJJ-UHFFFAOYSA-M 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
- 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
- 239000001993 wax Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 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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- B60—VEHICLES IN GENERAL
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- B60C1/0016—Compositions of the tread
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- C08C19/00—Chemical modification of rubber
- C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
- C08C19/42—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups
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- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
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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
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Abstract
Description
一つ又はそれ以上の実施態様において、分岐重合体には、複数枝分れした重合体が含まれる。多分岐重合体は、骨格と、少なくとも二つの分岐点と、該少なくとも二つの分岐点から伸びる少なくとも二つの枝とを含む。例えば、一つ又はそれ以上の実施態様の多分岐重合体を、下記式:
(β)n−φ−π−φ−(β)n
で表すことができる。
一つ又はそれ以上の実施態様において、分岐重合体には、官能化された枝分れ重合体が含まれる。官能化分岐重合体は、骨格と、該骨格の一方の末端に官能基と、該骨格の他方の末端に位置する分岐点と、該分岐点から伸びる少なくとも二つの枝とを含む。
(β)n−φ−π−α
で表すことができる。
一つ又はそれ以上の実施態様において、分岐重合体には、星型に枝分れしたランダム重合体が含まれる。星形に枝分れしたランダム重合体は、超分岐重合体と称されることがある。一つ又はそれ以上の実施態様において、星形に枝分れしたランダム重合体を単一の式で表すことは容易でないが、分子量及び分子構造の統計的分布である場合がある。一つ又はそれ以上の実施態様において、星形に枝分れしたランダム重合体は、一つ又はそれ以上の骨格と、二つ以上の枝と、二つ以上の分岐点と、一つ又はそれ以上の官能基とを含むことができる。
一つ又はそれ以上の実施態様において、分岐重合体には、樹枝状にグラフトした(dendrigraft)重合体が含まれる。一般に、樹枝状にグラフトした重合体は、星形に枝分れしたランダム重合体に比べてより規則正しい構造を示すことができるが、それにもかかわらず、樹枝状にグラフトした重合体を単一の式で表すことは容易でない。
一つ又はそれ以上の実施態様において、多分岐重合体は、モノ-リビング重合体を分岐剤と反応させ、分岐停止剤を形成し、次いで、多分岐重合体を形成させるために該分岐停止剤をジ-リビング重合体と反応させることで調製できる。
(ρ)m−χ−(γ)n
によって定義されることができる。
一つ又はそれ以上の実施態様において、官能化分岐重合体は、上記したもの等の分岐剤をリビング重合体の混合物と反応させることにより調製でき、ここで、該混合物には、複数のリビング重合体と複数の非官能性リビング重合体(即ち、官能基のないリビング重合体)とが含まれる。官能基を含む複数のリビング重合体は、複数の第一重合体と称される場合があり、官能基のない複数の重合体は、複数の第二リビング重合体と称される場合がある。
一つ又はそれ以上の実施態様においては、星形に枝分れしたランダム重合体は、分岐重合体を含む組成物にフリーラジカル源を与えることにより調製できる。
一つ又はそれ以上の実施態様において、複数枝分れして樹枝状にグラフトした重合体は、リビング重合体をグラフト化剤及び連鎖移動剤と反応させることで調製できる。
更に他の実施態様においては、特定の分岐重合体を合成し、追加的なカップリング又は枝分れを誘起するフリーラジカル源で該分岐重合体を処理することによって、有用な分岐重合体を調製することができる。一つ又はそれ以上の実施態様においては、ランタニド系の触媒系を用いることで、特定の分岐重合体を調製することができ、該重合体のフリーラジカル源での処理は、重合体に導入される過酸化物によって行われる。特定の実施態様においては、溶液中にて重合体を過酸化物で処理する。
で表されるオリゴマー状の線状アルミノキサン、及び一般式:
で表されるオリゴマー状の環状アルミノキサンを含む。ここで、xは1〜約100、好ましくは約10〜約50の整数であり;yは2〜約100、好ましくは約3〜約20の整数であり;各R1は、同一でも異なってもよいが、炭素原子を介してアルミニウム原子に結合する一価の有機基である。好ましくは、各R1は、限定されないが、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、アルカリール基、アリル基、アルキニル基等のヒドロカルビル基であり、ここで、各基は、1個の炭素原子又は該基を形成するのに妥当な最小数の炭素原子から約20個までの炭素原子を含有することが好ましい。これらヒドロカルビル基は、限定されないが、窒素原子、酸素原子、ホウ素原子、ケイ素原子、硫黄原子、リン原子等のヘテロ原子を含んでもよい。本願で使用されるアルミノキサンのモル数は、オリゴマー状のアルミノキサン分子のモル数というよりもアルミニウム原子のモル数を指すことに注意すべきである。この慣行は、アルミノキサンを利用する触媒の技術分野において一般に採用されている。
更に、本発明の一つ又はそれ以上の実施態様に従って調製された分岐重合体を処理し、該重合体を水素化することができる。これは、上記重合体の特定の使用において有利なことがある。
一つ又はそれ以上の実施態様においては、本願に開示の分岐重合体をタイヤ部品の製造に使用することができる。該タイヤ部品は、本発明の分岐重合体を単独で又は他のゴム状重合体と共に用いることによって製造できる。使用できる他のゴム状エラストマーには、天然エラストマー及び合成エラストマーが含まれる。合成エラストマーは、典型的に、共役ジエン単量体の重合から得られる。該共役ジエン単量体を、ビニル芳香族単量体等の他の単量体と共に共重合することができる。他のゴム状エラストマーは、エチレンを一種又はそれ以上のα-オレフィンと、任意には一種又はそれ以上のジエン単量体と共に重合することによって得ることができる。
多分岐重合体を、分岐停止剤を用いて調製した。8オンスのボトルに、ジイソプロペニルベンゼン0.58mLと、トリエチルアミン0.95mlと、1.33Mのs-ブチルリチウム5.1mLを加えた。該ボトルを50℃の水浴中で1時間混転した。この混転の後、1Mのリチウム-tert-ブトキシド7mLを加えた。同時に、24オンスのボトル11個に、ヘキサン154gと1,3-ブタジエン/ヘキサンブレンド(1,3-ブタジエンを21.7重量%含有)131gを投入した。各ボトルに、1.68Mのn-ブチルリチウム1.7mLを加えて、次に、50℃の水浴中に1時間置いた。次いで、該ボトルを室温の浴槽中で30分間混転した。その後、特性決定のため、ボトルの一つをイソプロパノール−BHT溶液で停止した。各ボトルに、1.29Mの四塩化ケイ素0.66mLを加えた。再度、ボトルを室温の浴槽中で30分間混転した。
様々な段階でのサンプルの分析は、以下に示すデータを与える。GPC分子量の結果は、線状重合体のみが絶対値であり、枝分れした種のMnデータは(少なく見積もった)近似値でしかないことに注意すべきである。
例1で調製された多分岐重合体を、50対50の重量比で線状重合体とブレンドした。線状重合体は、開始剤としてn-ブチルリチウムを、停止剤として水を用いてアニオン重合技術により調製された。線状重合体は、ビニルが7.4%で、Tgが-90℃で、Mnが37kg/モルで、Mw/Mnが1.04であることを特徴とした。
多分岐重合体を、分岐停止剤を用いて調製した。8オンスのボトルに、ジイソプロペニルベンゼン0.35mLと、トリエチルアミン0.57mlと、1.33Mのs-ブチルリチウム3.1mLを加えた。該ボトルを50℃の水浴中で1時間混転した。この混転の後、1Mのリチウム-tert-ブトキシド4.1mLを加えた。同時に、24オンスのボトル12個に、ヘキサン148gと1,3-ブタジエン/ヘキサンブレンド(1,3-ブタジエンを20.8重量%含有)137gを投入した。各ボトルに、1.54Mのn-ブチルリチウム0.93mLを加えて、次に、50℃の水浴中に1時間置いた。次いで、該ボトルを室温の浴槽中で30分間混転した。その後、特性決定のため、ボトルの一つをイソプロパノール−BHT溶液で停止した。他のボトルそれぞれに、1.29Mの四塩化ケイ素0.33mLを加えた。再度、ボトルを室温の浴槽中で30分間混転した。
官能化分岐重合体を以下のように調製した。2ガロンのステンレス鋼製反応器に、ヘキサン2.88lbsと1,3-ブタジエン/ヘキサンブレンド(1,3-ブタジエンを22重量%含有)4.75lbsを投入した。該反応器のジャケットを150°Fに加熱した。そのバッチが138°Fに達したとき、1.23Mのトリブチルスズリチウム4.3mLを加えて、ヘキサン約20mLで希釈した。重合は、反応の16分後に174.5°Fで発熱した。25分後、分析のためサンプルを落とした。該反応器に、第二開始剤であるn-ブチルリチウム(1.54Mのもの10.2mL)を加え、続けて1,3-ブタジエン/ヘキサンブレンド(1,3-ブタジエンを22重量%含有)2.10lbsを加えた。第二発熱ピークが、16分後に159.6°Fで観察された。分析のため、20分後にサンプルを落とし、該反応器に0.86Mの四塩化ケイ素6.0mLを加えた。1時間後、分析のため、サンプルを落とし、該反応器にn-ブチルリチウム2.0mLを加えた。反応の1.5時間後、反応混合物を冷却し、BHT含有イソプロパノール中に落とした。その後、凝固した重合体を単離してドラム乾燥させた。
官能化分岐重合体を以下のように調製した。2ガロンのステンレス鋼製バッチ反応器に、ヘキサン2.94lbsと1,3-ブタジエン/ヘキサンブレンド(1,3-ブタジエンを22重量%含有)4.34lbsを投入した。該反応器のジャケットを150°Fに加熱した。そのバッチが138°Fに達したとき、1.23Mのトリブチルスズリチウム3.9mLを加えて、ヘキサン約20mLで希釈した。重合は、反応の16分後に167.5°Fで発熱した。20分後、分析のためサンプルを落とした。該反応器に、第二開始剤であるn-ブチルリチウム(1.54Mのもの18.5mL)を加え、続けて1,3-ブタジエン/ヘキサンブレンド(1,3-ブタジエンを22重量%含有)2.43lbsを加えた。第二発熱ピークが、15分後に160.5°Fで観察された。分析のため、18分後にサンプルを落とし、該反応器に0.86Mの四塩化ケイ素6.9mLを加えた。1.5時間後、分析のため、サンプルを落とし、該反応器にn-ブチルリチウム2.3mLを加えた。反応の1.5時間後、反応混合物を冷却し、BHT含有イソプロパノール中に落とした。その後、凝固した重合体を単離してドラム乾燥させた。
官能化分岐重合体を以下のように調製した。2ガロンのステンレス鋼製バッチ反応器に、ヘキサン2.94lbsと1,3-ブタジエン/ヘキサンブレンド(1,3-ブタジエンを21.9重量%含有)4.40lbsを投入した。該反応器のジャケットを150°Fに加熱した。そのバッチが130°Fに達したとき、1.23Mのトリブチルスズリチウム3.9mLを加えて、ヘキサン約20mLで希釈した。重合は、反応の17分後に177.3°Fで発熱した。23分後、分析のためサンプルを落とした。該反応器に、第二開始剤であるn-ブチルリチウム(1.54Mのもの18.5mL)を加え、続けて1,3-ブタジエン/ヘキサンブレンド(1,3-ブタジエンを21.9重量%含有)2.45lbsを加えた。第二発熱ピークが、15分後に162.5°Fで観察された。分析のため、30分後にサンプルを落とし、該反応器に0.86Mの四塩化ケイ素9.7mLを加えた。1時間後、分析のため、サンプルを落とし、該反応器にn-ブチルリチウム2.3mLを加えた。反応の1.5時間後、反応混合物を冷却し、BHT含有イソプロパノール中に落とした。その後、凝固した重合体を単離してドラム乾燥させた。
星形重合体を以下のように調製した。2ガロンのステンレス鋼製バッチ反応器に、ヘキサン2.82lbsと1,3-ブタジエン/ヘキサンブレンド(1,3-ブタジエンを22.9重量%含有)5.90lbsを投入した。該反応器のジャケットを150°Fに加熱した。そのバッチが141°Fに達したとき、1.68Mのn-ブチルリチウム10.5mLを加えて、ヘキサン約20mLで希釈した。重合は、反応の13分後に189.6°Fで発熱した。17分後、分析のためサンプルを落とした。該反応器に、OOPS調整剤(1.60M;10mL)を加え、続けて0.87Mの四塩化ケイ素5mLを加えた。3.5時間後、分析のためサンプルを落とし、該反応器にn-ブチルリチウム2.0mLを加えた(依然としてそこに存在し、後処理の後に重合体中にゲルの形成を支持する塩化ケイ素をいずれも停止させる)。反応の1時間後、反応混合物を冷却し、BHT含有イソプロパノール中に落とした。その後、凝固した重合体を単離してドラム乾燥させた。重合体はゲルを1.5%含有した。
多分岐重合体(カップリングした星形)を以下のように調製した。ブラベンダーミキサー中120℃で5分間50RPMの混合速度によって、例7の星形重合体を2,2'-アゾビス-(2-イソブチロニトリル)(AIBN)0.5phrと反応させた。この反応の後、該ブラベンダー中の変性重合体に、ブチル化ヒドロキシルトルエン(BHT)酸化防止剤1.0phrを加え、50RPM及び120℃にて1分間混合した。最終変性重合体のGPC結果は、最初の星型分子の32%がこの方法によって無作為に一体となってカップリングされたことを示す。最終重合体は、ゲルを2.0%含有した。
多分岐重合体(カップリングした星形)を以下のように調製した。ブラベンダーミキサー中120℃で5分間50RPMの混合速度によって、例5の星形重合体を2,2'-アゾビス-(2-イソブチロニトリル)(AIBN)2.0phrと反応させた。この反応の後、該ブラベンダー中の変性重合体に、ブチル化ヒドロキシルトルエン(BHT)酸化防止剤1.0phrを加え、50RPM及び120℃にて1分間混合した。最終変性重合体のGPC結果は、最初の星型分子の47%がこの方法によって無作為に一体となってカップリングされたことを示す。最終重合体は、ゲルを11.5%含有した。
例9で調製した多分岐重合体(カップリングした星形)を、50対50の重量比で線状重合体とブレンドした。線状重合体は、開始剤としてn-ブチルリチウムを、停止剤として水を用いてアニオン重合技術により調製された。線状重合体は、ビニルが7.4%で、Tgが-90℃で、Mnが37kg/モルで、Mw/Mnが1.04であることを特徴とした。
樹枝状にグラフトした重合体を、以下に示す方法に従って調製した。1ガロンのステンレス鋼製反応器に、工業銘柄ヘキサン(水を<5ppmに乾燥し、N2圧を受けたもの)2.0lbsを投入した。次いで、該反応器に、nBuLi4.62mmolとK-t-アミレート0.18mmolとを投入した。分離充填型タンクに、ヘキサン1.0lb、1,3-ブタジエン22%のヘキサン溶液のブレンド3.15lb、ジビニルベンゼン6.1mmol及びジブチルアミン3.1mmolの重さを量って供給した。反応器の加熱ジャケットを160°Fに設定した。該反応器が120°Fに達したとき、単量体、架橋剤及び移動剤のブレンドを0.06lb/分で計量しながら反応器に供給した。計量時間は85分であり、反応器は158°Fの温度に達した。計量が完了してから15分後に、酸化防止剤のジブチル-p-クレゾールを含有するイソプロパノール中で重合体溶液を沈殿させた。沈殿した重合体をドラム乾燥し、収率92%を得た。重合体の1,2-付加(ビニル含有量)は8%であった。重合体のGPC特性は、Mn=82.1kg/mol及びMw/Mn=2.50を与えた。GPC分子量の結果は、線状重合体のみが絶対値であり、枝分れした種のMnデータは(少なく見積もった)近似値でしかないことに注意すべきである。
K-t-アミレートの代わりに2,2-ビス(テトラヒドロフリル)プロパン0.4mmolを用いた以外は、例11と同様な手順に従った。重合体の1,2-付加(ビニル含有量)は27%であった。重合体のGPC特性は、Mn=83.2kg/mol及びMw/Mn=2.99を与えた。GPC分子量の結果は、線状重合体のみが絶対値であり、枝分れした種のMnデータは(少なく見積もった)近似値でしかないことに注意すべきである。
K-t-アミレートの代わりに2,2-ビス(テトラヒドロフリル)プロパン2.56mmolを用いた以外は、例11と同様な手順に従った。重合体の1,2-付加(ビニル含有量)は53%であった。重合体のGPC特性は、Mn=62.6kg/mol及びMw/Mn=2.09を与えた。GPC分子量の結果は、線状重合体のみが絶対値であり、枝分れした種のMnデータは(少なく見積もった)近似値でしかないことに注意すべきである。
例2の多分岐重合体ブレンドを用いて、ゴム組成物を調製し、ゴム加硫物に硬化させた。また、比較のサンプルを調製して試験した。組成物の処方を表Iに与える。該表に与えられる量は、特定の定めがない限り、重量部で示される。
先の例と同様な方法で、表IIIに示す官能化分岐重合体及び多分岐重合体(カップリングした星形)を用いて、ゴム組成物及び加硫ゴムを調製した。各サンプルの重合体成分を、該サンプルに行った各種試験結果と共に表IIIに示す。
先の例と同様な方法で、例11〜13の樹枝状にグラフトした重合体を用いて、ゴム組成物及び加硫ゴムを調製した。各サンプルの重合体成分を、該サンプルに行った各種試験結果と共に表IVに示す。
2ガロンの反応器に、ヘキサン3.05lbsとブタジエンブレンド(ヘキサン中22wt%)6.45lbsとを投入した。反応器のジャケットを80°Fに加熱した。バッチが74°Fに達したとき、1Mの水素化ジイソブチルアルミニウム(DIBAH)11mL、0.588Mのネオジムバーサチック酸塩1.87mL、0.09Mのニッケルオクトアート0.24mL及び1Mのジエチルアルミニウムクロリド3.3mLを同時に加えて、ヘキサン約20mLで希釈した。次に、反応器のジャケットを150°Fに加熱した。重合は、反応の35分後に188.1°Fに発熱した。30分後、バッチを210°Fに加熱した。分析のため、サンプルを落とした。反応器に過酸化ラウロイル溶液(0.044g/mLで203mL)を加えた。1時間後、バッチを冷却し、ブチル化ヒドロキシトルエン(BHT)を含有するイソプロパノール中に落とした。その後、生成物を単離し、ドラム乾燥させた。以下に示すGPCの結果は、線状重合体のみが有効であり、従って、Mw及びMnの値は、近似値でしかない。
Claims (14)
- (a)骨格と、少なくとも二つの分岐点と、該分岐点のそれぞれから伸びる少なくとも二つの枝とを含む重合体であって、前記骨格が該骨格の絡み合い分子量の少なくとも2.5倍の長さであり、前記枝がそれぞれ該枝の絡み合い長さの少なくとも1倍の長さであり、前記骨格のガラス転移温度が0℃未満であり、前記骨格及び前記枝が互いに混和できる重合体、及び
(b)対向した末端を有する骨格と、一方の対向末端に位置する少なくとも一つの分岐点と、該少なくとも一つの分岐点から伸びる少なくとも二つの枝と、他方の対向末端にて充填剤と相互作用する官能基とを含む重合体であって、前記骨格が該骨格の絡み合い長さの少なくとも2.5倍の長さであり、前記枝がそれぞれ該枝の絡み合い長さの少なくとも1倍の長さであり、前記骨格のガラス転移温度が0℃未満であり、前記骨格及び前記枝が互いに混和できる重合体
よりなる群から選択される重合体の加硫物を含むタイヤ部品。 - 重合体を製造する方法であって、
(a)モノ-リビング重合体であって、該モノ-リビング重合体の絡み合い長さの少なくとも1倍の長さである重合体を用意する工程と、
(b)前記モノ-リビング重合体を分岐剤と反応させる工程であって、前記分岐剤が少なくとも三つの反応部位を含み、前記反応部位の当量がモノ-リビング重合体のモルを超え、それにより、分岐停止剤を形成する工程と、
(c)前記分岐停止剤をジ-リビング重合体と反応させる工程であって、前記ジ-リビング重合体が該ジ-リビング重合体の絡み合い長さの少なくとも2.5倍の長さである工程と
を含む方法。 - 重合体を製造する方法であって、
(a)単量体を、官能基を有するアニオン重合開始剤と接触させ、重合媒体を形成し、官能化リビング重合体を合成する工程と、
(b)前記官能化リビング重合体の合成を、該官能化リビング重合体が該官能化リビング重合体の絡み合い分子量の少なくとも2.5倍の長さとなるまで進めさせる工程と、
(c)前記工程(b)の後、前記重合媒体に、追加の単量体と、非官能性のアニオン重合開始剤とを加えて、非官能化リビング重合体を合成する工程と、
(d)前記非官能化リビング重合体の合成を、該非官能化リビング重合体が該非官能化リビング重合体の絡み合い分子量の少なくとも1倍の長さとなるまで進めさせる工程と、
(e)前記工程(d)の後、前記重合媒体に、カップリング剤を加える工程であって、前記カップリング剤が少なくとも三つの反応部位を含む工程と
を含む方法。 - 重合体を製造する方法であって、
(a)複数の重合体分子を用意する工程であって、前記重合体分子が、少なくとも一つの分岐点を有する枝分れ分子を含み、少なくとも三つの枝が前記少なくとも一つの分岐点から伸び、前記枝が該枝の絡み合い分子量の少なくとも1倍の長さである工程と、
(b)重合媒体にフリーラジカル開始剤を加える工程と
を含む方法。 - 重合体を製造する方法であって、
(a)単量体を、アニオン重合開始剤と接触させ、重合媒体を形成し、リビング重合体を合成する工程と、
(b)前記リビング重合体の合成を、該リビング重合体が該リビング重合体の絡み合い分子量の少なくとも1倍の長さとなるまで進めさせる工程と、
(c)前記重合媒体に、グラフト化剤と、連鎖移動剤と、任意に追加の単量体とを加える工程であって、グラフト化剤対アニオン重合開始剤の比が約0.1対1〜約2対1であり、連鎖移動剤対グラフト化剤の比が約0.25対1〜約2対1である工程と
を含む方法。 - 分岐重合体を製造する方法であって、
(a)共役ジエン単量体を、(i)ランタニド化合物、(ii)アルキル化剤、(iii)ニッケル含有化合物及び(iv)ハロゲン源の組み合わせ又は反応生成物である触媒系で重合させて、高シスポリジエンを形成させる工程と、
(b)前記高シスポリジエンをフリーラジカル源でカップリングする工程と
を含む方法。 - 更に、得られる重合体を水素化する工程を含むことを特徴とする請求項2〜6のいずれかに記載の方法。
- 請求項1に記載のタイヤ又は請求項2〜7のいずれかに記載の方法によって調製した重合体の加硫物を含むタイヤ部品。
- 前記カップリング工程が、高シスポリジエンを溶解する有機溶媒中で行われることを特徴とする請求項6に記載の方法。
- 前記重合工程が有機溶媒中で行われ、前記高シスポリジエン及び触媒を前記カップリング工程の前に失活させることを特徴とする請求項6に記載の方法。
- 前記骨格が該骨格の絡み合い長さの少なくとも3倍の長さであり、前記枝がそれぞれ該枝の絡み合い長さの少なくとも1.5倍の長さであることを特徴とする請求項1に記載のタイヤ。
- 前記骨格が該骨格の絡み合い長さの少なくとも4倍の長さであり、前記枝がそれぞれ該枝の絡み合い長さの少なくとも2倍の長さであることを特徴とする請求項11に記載のタイヤ。
- (a)骨格と、少なくとも二つの分岐点と、該分岐点のそれぞれから伸びる少なくとも二つの枝とを含む重合体であって、前記骨格が該骨格の絡み合い分子量の少なくとも2.5倍の長さであり、前記枝がそれぞれ該枝の絡み合い長さの少なくとも1倍の長さであり、前記骨格のガラス転移温度が0℃未満であり、前記骨格及び前記枝が互いに混和できる重合体、及び
(b)対向した末端を有する骨格と、一方の対向末端に位置する少なくとも一つの分岐点と、該少なくとも一つの分岐点から伸びる少なくとも二つの枝と、他方の対向末端にて充填剤と相互作用する官能基とを含む重合体であって、前記骨格が該骨格の絡み合い長さの少なくとも2.5倍の長さであり、前記枝がそれぞれ該枝の絡み合い長さの少なくとも1倍の長さであり、前記骨格のガラス転移温度が0℃未満であり、前記骨格及び前記枝が互いに混和できる重合体
よりなる群から選択される分岐重合体を含む重合体組成物の加硫物を含むタイヤ部品。 - ゴム組成物が、前記分岐重合体に加えて、不飽和重合体を含み、前記分岐重合体が水素化されることを特徴とする請求項13に記載のタイヤ。
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JP2014513741A (ja) * | 2011-05-09 | 2014-06-05 | 株式会社ブリヂストン | 高シスポリジエンの調製方法 |
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JP5829297B2 (ja) | 2015-12-09 |
WO2008045372A2 (en) | 2008-04-17 |
US20120108755A1 (en) | 2012-05-03 |
JP5508016B2 (ja) | 2014-05-28 |
BRPI0717496A2 (pt) | 2014-06-24 |
CN101563398B (zh) | 2012-10-24 |
US20100137520A1 (en) | 2010-06-03 |
US8933181B2 (en) | 2015-01-13 |
KR101457981B1 (ko) | 2014-11-05 |
EP2066735A2 (en) | 2009-06-10 |
WO2008045372A3 (en) | 2009-03-26 |
BRPI0717496B1 (pt) | 2018-06-26 |
KR20090085610A (ko) | 2009-08-07 |
ZA200902284B (en) | 2010-07-28 |
CN101563398A (zh) | 2009-10-21 |
US8119736B2 (en) | 2012-02-21 |
JP2014159571A (ja) | 2014-09-04 |
BR122018004305B1 (pt) | 2019-02-19 |
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