JP4523410B2 - 共役ジエン及びビニル芳香族化合物を用いたポリメリセートの生成方法、それによって生成されるポリメリセート、及びその使用 - Google Patents
共役ジエン及びビニル芳香族化合物を用いたポリメリセートの生成方法、それによって生成されるポリメリセート、及びその使用 Download PDFInfo
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- JP4523410B2 JP4523410B2 JP2004528431A JP2004528431A JP4523410B2 JP 4523410 B2 JP4523410 B2 JP 4523410B2 JP 2004528431 A JP2004528431 A JP 2004528431A JP 2004528431 A JP2004528431 A JP 2004528431A JP 4523410 B2 JP4523410 B2 JP 4523410B2
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- Prior art keywords
- organic compound
- lithium
- polymerization
- polymerisate
- carbon atoms
- 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.)
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- 150000001993 dienes Chemical class 0.000 title claims abstract description 12
- -1 vinyl aromatic compound Chemical class 0.000 title claims description 31
- 229920002554 vinyl polymer Polymers 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 238000000034 method Methods 0.000 claims abstract description 44
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims abstract description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 32
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 30
- 229910052744 lithium Inorganic materials 0.000 claims description 21
- 239000000178 monomer Substances 0.000 claims description 20
- 238000006116 polymerization reaction Methods 0.000 claims description 18
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 16
- 229910052783 alkali metal Inorganic materials 0.000 claims description 11
- 150000001340 alkali metals Chemical class 0.000 claims description 11
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 10
- 239000003513 alkali Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 150000002894 organic compounds Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000001983 dialkylethers Chemical class 0.000 claims description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 239000007810 chemical reaction solvent Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000003431 cross linking reagent Substances 0.000 claims description 2
- BDLXTDLGTWNUFM-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxy]ethanol Chemical compound CC(C)(C)OCCO BDLXTDLGTWNUFM-UHFFFAOYSA-N 0.000 claims 1
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 claims 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims 1
- 239000005049 silicon tetrachloride Substances 0.000 claims 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 10
- 239000003426 co-catalyst Substances 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 50
- 239000003607 modifier Substances 0.000 description 21
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 20
- 229920000642 polymer Polymers 0.000 description 17
- 239000000243 solution Substances 0.000 description 15
- 229920003048 styrene butadiene rubber Polymers 0.000 description 14
- 230000000694 effects Effects 0.000 description 13
- 229920001971 elastomer Polymers 0.000 description 13
- 239000005060 rubber Substances 0.000 description 13
- 239000002174 Styrene-butadiene Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 238000010348 incorporation Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000005096 rolling process Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- WEERVPDNCOGWJF-UHFFFAOYSA-N 1,4-bis(ethenyl)benzene Chemical compound C=CC1=CC=C(C=C)C=C1 WEERVPDNCOGWJF-UHFFFAOYSA-N 0.000 description 3
- 239000002879 Lewis base Substances 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 3
- 150000007527 lewis bases Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000002900 organolithium compounds Chemical class 0.000 description 3
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 2
- SYENRPHLJLKTED-UHFFFAOYSA-N 1,3,5-tris(ethenyl)benzene Chemical compound C=CC1=CC(C=C)=CC(C=C)=C1 SYENRPHLJLKTED-UHFFFAOYSA-N 0.000 description 2
- RCJMVGJKROQDCB-UHFFFAOYSA-N 2-methylpenta-1,3-diene Chemical compound CC=CC(C)=C RCJMVGJKROQDCB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- CGRKYEALWSRNJS-UHFFFAOYSA-N sodium;2-methylbutan-2-olate Chemical compound [Na+].CCC(C)(C)[O-] CGRKYEALWSRNJS-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-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 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- PRJNEUBECVAVAG-UHFFFAOYSA-N 1,3-bis(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1 PRJNEUBECVAVAG-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- VDNSZPNSUQRUMS-UHFFFAOYSA-N 1-cyclohexyl-4-ethenylbenzene Chemical compound C1=CC(C=C)=CC=C1C1CCCCC1 VDNSZPNSUQRUMS-UHFFFAOYSA-N 0.000 description 1
- WJNKJKGZKFOLOJ-UHFFFAOYSA-N 1-dodecyl-4-ethenylbenzene Chemical compound CCCCCCCCCCCCC1=CC=C(C=C)C=C1 WJNKJKGZKFOLOJ-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- JHTICDZLXFNVKL-UHFFFAOYSA-N 1-ethenyl-4-(4-phenylbutyl)benzene Chemical compound C1=CC(C=C)=CC=C1CCCCC1=CC=CC=C1 JHTICDZLXFNVKL-UHFFFAOYSA-N 0.000 description 1
- VVTGQMLRTKFKAM-UHFFFAOYSA-N 1-ethenyl-4-propylbenzene Chemical compound CCCC1=CC=C(C=C)C=C1 VVTGQMLRTKFKAM-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- HOFBOABHMRNQJZ-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxy]butan-1-ol Chemical compound CCC(CO)OC(C)(C)C HOFBOABHMRNQJZ-UHFFFAOYSA-N 0.000 description 1
- KXYAVSFOJVUIHT-UHFFFAOYSA-N 2-vinylnaphthalene Chemical compound C1=CC=CC2=CC(C=C)=CC=C21 KXYAVSFOJVUIHT-UHFFFAOYSA-N 0.000 description 1
- IGLWCQMNTGCUBB-UHFFFAOYSA-N 3-methylidenepent-1-ene Chemical compound CCC(=C)C=C IGLWCQMNTGCUBB-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- DXFURPHVJQITAC-UHFFFAOYSA-N 4-benzyl-1-ethenyl-2-ethylbenzene Chemical compound C1=C(C=C)C(CC)=CC(CC=2C=CC=CC=2)=C1 DXFURPHVJQITAC-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- FHQRDEDZJIFJAL-UHFFFAOYSA-N 4-phenylmorpholine Chemical compound C1COCCN1C1=CC=CC=C1 FHQRDEDZJIFJAL-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910003902 SiCl 4 Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- NTYDXFVCCCPXRG-UHFFFAOYSA-N [Li]C(C)(C)CC(C)(C)C Chemical compound [Li]C(C)(C)CC(C)(C)C NTYDXFVCCCPXRG-UHFFFAOYSA-N 0.000 description 1
- SHJXVDAAVHAKFB-UHFFFAOYSA-N [Li]CCCCCCCCCC Chemical compound [Li]CCCCCCCCCC SHJXVDAAVHAKFB-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- RTACIUYXLGWTAE-UHFFFAOYSA-N buta-1,3-diene;2-methylbuta-1,3-diene;styrene Chemical compound C=CC=C.CC(=C)C=C.C=CC1=CC=CC=C1 RTACIUYXLGWTAE-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- IQIWJEAPUNWDLC-UHFFFAOYSA-N lithium;octane Chemical compound [Li+].CCCCCCC[CH2-] IQIWJEAPUNWDLC-UHFFFAOYSA-N 0.000 description 1
- SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910052700 potassium Chemical group 0.000 description 1
- 239000011591 potassium Chemical group 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
- C08F236/10—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 with vinyl-aromatic monomers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/46—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 alkali metals
- C08F4/48—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 alkali metals selected from lithium, rubidium, caesium or francium
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- 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
- C08C19/44—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 of polymers containing metal atoms exclusively at one or both ends of the skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerization Catalysts (AREA)
- Polyesters Or Polycarbonates (AREA)
- Graft Or Block Polymers (AREA)
- Tires In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10234746A DE10234746B4 (de) | 2002-07-30 | 2002-07-30 | Verfahren zur Herstellung von Polymerisaten unter Verwendung von konjugierten Dienen und vinylaromatischen Verbindungen, nach diesem Verfahren hergestellte Polymerisate und deren Verwendung |
| PCT/DE2003/002490 WO2004016666A1 (de) | 2002-07-30 | 2003-07-24 | Verfahren zur herstellung von polymerisaten unter verwendung von konjugierten dienen und vinylaromatischen verbindungen, nach diesem verfahren hergestellte polymerisate und deren verwendung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006500435A JP2006500435A (ja) | 2006-01-05 |
| JP2006500435A5 JP2006500435A5 (https=) | 2006-09-07 |
| JP4523410B2 true JP4523410B2 (ja) | 2010-08-11 |
Family
ID=7714810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004528431A Expired - Fee Related JP4523410B2 (ja) | 2002-07-30 | 2003-07-24 | 共役ジエン及びビニル芳香族化合物を用いたポリメリセートの生成方法、それによって生成されるポリメリセート、及びその使用 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7151147B2 (https=) |
| EP (1) | EP1525239B1 (https=) |
| JP (1) | JP4523410B2 (https=) |
| KR (1) | KR100897844B1 (https=) |
| CN (1) | CN1303119C (https=) |
| AT (1) | ATE373027T1 (https=) |
| AU (1) | AU2003258461A1 (https=) |
| BR (1) | BR0312910B8 (https=) |
| CA (1) | CA2493620A1 (https=) |
| DE (2) | DE10234746B4 (https=) |
| ES (1) | ES2294353T3 (https=) |
| MX (1) | MXPA05001225A (https=) |
| NO (1) | NO20050777L (https=) |
| PL (1) | PL373291A1 (https=) |
| RU (1) | RU2326895C2 (https=) |
| WO (1) | WO2004016666A1 (https=) |
| ZA (1) | ZA200500814B (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5357012B2 (ja) * | 2007-03-26 | 2013-12-04 | 旭化成ケミカルズ株式会社 | 熱可塑性組成物及びその成形体 |
| DE102009009531A1 (de) * | 2009-02-18 | 2010-08-19 | Lanxess Deutschland Gmbh | Initiatorsystem zur Synthese von Hochvinyl-Dienkautschuken, ein Verfahren zur Herstellung und dessen Verwendung zur Herstellung von Hochvinyl-Dienkautschuken |
| CN103459431B (zh) | 2011-05-27 | 2015-01-21 | 旭化成化学株式会社 | 氢化共轭二烯系共聚物的制造方法 |
| ES2695042T3 (es) | 2011-06-22 | 2018-12-28 | Trinseo Europe Gmbh | Caucho estireno-butadieno con alto contenido de estireno y vinilo con distribución de peso molecular estrecha y procedimientos para su preparación |
| CN102977268B (zh) * | 2011-09-05 | 2015-04-15 | 中国石油化工股份有限公司 | 共轭二烯烃聚合物和合成橡胶及其制备方法和应用 |
| CN104098810B (zh) * | 2013-04-12 | 2016-02-24 | 中国石油化工股份有限公司 | 一种组合物及其在制备阻尼材料中的应用和一种阻尼材料及其制备方法 |
| CA2960005C (en) * | 2014-09-04 | 2023-02-14 | Kuraray Co., Ltd. | Method for producing anionic polymer |
| KR102464763B1 (ko) | 2017-11-17 | 2022-11-08 | 주식회사 엘지화학 | 블록 공중합체 조성물 제조방법, 이로부터 제조된 블록 공중합체 조성물을 포함하는 아스팔트 조성물 |
| EP4148075A4 (en) * | 2020-05-21 | 2023-11-08 | China Petroleum & Chemical Corporation | LIQUID BUTYLBENZENE POLYMER, PRODUCTION PROCESS THEREOF AND APPLICATION THEREOF, AS WELL AS COMPOSITION, POLYMER COATING, ADHESIVE AND CROSSLINKING AGENT |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3294768A (en) * | 1963-11-14 | 1966-12-27 | Phillips Petroleum Co | Preparation of conjugated diene polymers |
| US3496154A (en) * | 1965-10-15 | 1970-02-17 | Phillips Petroleum Co | Random copolymerization |
| US3781261A (en) * | 1972-02-03 | 1973-12-25 | Firestone Tire & Rubber Co | Metalating rubber polymers |
| JPS5465787A (en) * | 1977-11-07 | 1979-05-26 | Denki Kagaku Kogyo Kk | Preparation of conjugated diolefin polymer |
| JPS57100112A (en) * | 1980-12-16 | 1982-06-22 | Asahi Chem Ind Co Ltd | Perfectly random styrene-butadiene copolymer rubber |
| GB8316052D0 (en) * | 1983-06-13 | 1983-07-20 | Shell Int Research | Elastomeric copolymers |
| DE3724870A1 (de) * | 1987-07-28 | 1989-02-09 | Huels Chemische Werke Ag | Verfahren zur herstellung von polymerisaten auf basis von konjugierten dienen und ggf. monovinylaromatischen verbindungen |
| CA2035229A1 (en) * | 1990-10-22 | 1992-04-23 | Wen-Liang Hsu | Process for preparing a rubbery terpolymer of styrene, isoprene and butadiene |
| US5534592A (en) * | 1995-09-22 | 1996-07-09 | The Goodyear Tire & Rubber Company | High performance blend for tire treads |
| EP0798339B1 (en) | 1996-03-29 | 2002-06-05 | Bridgestone Corporation | Styrene-butadiene copolymer and rubber composition comprising the copolymer |
| DE19613195A1 (de) * | 1996-04-02 | 1997-10-09 | Huels Chemische Werke Ag | Reifenlaufflächen mit geringem Rollwiderstand und verbessertem ABS-Bremsen |
| DE19941314A1 (de) * | 1999-08-31 | 2001-03-01 | Bayer Ag | Verfahren zur Herstellung eines Copolymerisats auf der Basis von vinylaromatischen Verbindungen und konjugierten Dienen sowie dessen Verwendung zur Herstellung von Vulkanisaten mit einem hervorragenden Dämpfungsverhalten |
| DE10036055A1 (de) * | 2000-07-25 | 2002-02-07 | Bayer Ag | Verfahren zur Herstellung von di- oder trifunktionellen Initiatorsystemen auf Lithiumbasis sowie deren Verwendung |
| DE10053324A1 (de) * | 2000-10-27 | 2002-05-08 | Basf Ag | Verfahren zum Kettenabbruch bei der anionischen Polymerisation |
| DE10105401A1 (de) * | 2001-02-07 | 2002-08-22 | Bayer Ag | Kontinuierliches Verfahren zur Herstellung von Elastomeren |
| EP1453869A2 (de) * | 2001-11-23 | 2004-09-08 | Walter Hellermann | Mikrostrukturregler für die anionische polymerisation |
-
2002
- 2002-07-30 DE DE10234746A patent/DE10234746B4/de not_active Expired - Fee Related
-
2003
- 2003-07-24 KR KR1020057001690A patent/KR100897844B1/ko not_active Expired - Fee Related
- 2003-07-24 DE DE50308182T patent/DE50308182D1/de not_active Expired - Lifetime
- 2003-07-24 CN CNB038182807A patent/CN1303119C/zh not_active Expired - Fee Related
- 2003-07-24 WO PCT/DE2003/002490 patent/WO2004016666A1/de not_active Ceased
- 2003-07-24 EP EP03787730A patent/EP1525239B1/de not_active Expired - Lifetime
- 2003-07-24 AT AT03787730T patent/ATE373027T1/de not_active IP Right Cessation
- 2003-07-24 MX MXPA05001225A patent/MXPA05001225A/es active IP Right Grant
- 2003-07-24 PL PL03373291A patent/PL373291A1/xx unknown
- 2003-07-24 US US10/523,180 patent/US7151147B2/en not_active Expired - Fee Related
- 2003-07-24 RU RU2005105558/04A patent/RU2326895C2/ru not_active IP Right Cessation
- 2003-07-24 BR BRPI0312910-1A patent/BR0312910B8/pt not_active IP Right Cessation
- 2003-07-24 AU AU2003258461A patent/AU2003258461A1/en not_active Abandoned
- 2003-07-24 ES ES03787730T patent/ES2294353T3/es not_active Expired - Lifetime
- 2003-07-24 CA CA002493620A patent/CA2493620A1/en not_active Abandoned
- 2003-07-24 JP JP2004528431A patent/JP4523410B2/ja not_active Expired - Fee Related
-
2005
- 2005-01-27 ZA ZA200500814A patent/ZA200500814B/xx unknown
- 2005-02-14 NO NO20050777A patent/NO20050777L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| RU2326895C2 (ru) | 2008-06-20 |
| BR0312910B8 (pt) | 2013-02-19 |
| ATE373027T1 (de) | 2007-09-15 |
| CN1303119C (zh) | 2007-03-07 |
| KR20050033638A (ko) | 2005-04-12 |
| ZA200500814B (en) | 2006-07-26 |
| RU2005105558A (ru) | 2005-08-10 |
| WO2004016666A1 (de) | 2004-02-26 |
| CA2493620A1 (en) | 2004-02-26 |
| DE50308182D1 (de) | 2007-10-25 |
| KR100897844B1 (ko) | 2009-05-15 |
| CN1671760A (zh) | 2005-09-21 |
| US7151147B2 (en) | 2006-12-19 |
| BR0312910B1 (pt) | 2013-01-08 |
| US20060122343A1 (en) | 2006-06-08 |
| NO20050777L (no) | 2005-02-14 |
| DE10234746A1 (de) | 2003-02-27 |
| DE10234746B4 (de) | 2004-04-29 |
| JP2006500435A (ja) | 2006-01-05 |
| PL373291A1 (en) | 2005-08-22 |
| AU2003258461A1 (en) | 2004-03-03 |
| MXPA05001225A (es) | 2005-10-18 |
| EP1525239A1 (de) | 2005-04-27 |
| ES2294353T3 (es) | 2008-04-01 |
| BR0312910A (pt) | 2005-06-14 |
| EP1525239B1 (de) | 2007-09-12 |
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