JP6665145B2 - ブタジエン−スチレン線状共重合体、その調製方法および組成物、ならびに芳香族ビニル樹脂およびその調製方法 - Google Patents
ブタジエン−スチレン線状共重合体、その調製方法および組成物、ならびに芳香族ビニル樹脂およびその調製方法 Download PDFInfo
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- JP6665145B2 JP6665145B2 JP2017207946A JP2017207946A JP6665145B2 JP 6665145 B2 JP6665145 B2 JP 6665145B2 JP 2017207946 A JP2017207946 A JP 2017207946A JP 2017207946 A JP2017207946 A JP 2017207946A JP 6665145 B2 JP6665145 B2 JP 6665145B2
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- butadiene
- solution
- reaction
- styrene
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- 239000000203 mixture Substances 0.000 title claims description 162
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 title claims description 139
- 229920005684 linear copolymer Polymers 0.000 title claims description 138
- 239000011347 resin Substances 0.000 title claims description 134
- 229920005989 resin Polymers 0.000 title claims description 134
- 229920002554 vinyl polymer Polymers 0.000 title claims description 80
- 238000002360 preparation method Methods 0.000 title description 5
- 238000006243 chemical reaction Methods 0.000 claims description 234
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 180
- 229920000642 polymer Polymers 0.000 claims description 176
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 146
- 229920002857 polybutadiene Polymers 0.000 claims description 129
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 128
- 239000005064 Low cis polybutadiene Substances 0.000 claims description 126
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 121
- 238000006116 polymerization reaction Methods 0.000 claims description 98
- 238000000034 method Methods 0.000 claims description 90
- 238000009826 distribution Methods 0.000 claims description 89
- 239000003999 initiator Substances 0.000 claims description 75
- 239000001569 carbon dioxide Substances 0.000 claims description 71
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 71
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 69
- 150000001875 compounds Chemical class 0.000 claims description 63
- 239000012744 reinforcing agent Substances 0.000 claims description 61
- 125000001979 organolithium group Chemical group 0.000 claims description 58
- 239000000178 monomer Substances 0.000 claims description 54
- 230000002902 bimodal effect Effects 0.000 claims description 51
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 49
- 239000002981 blocking agent Substances 0.000 claims description 44
- -1 aluminum compound Chemical class 0.000 claims description 36
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 33
- 230000000977 initiatory effect Effects 0.000 claims description 31
- 150000002901 organomagnesium compounds Chemical class 0.000 claims description 31
- 238000005859 coupling reaction Methods 0.000 claims description 25
- 239000012745 toughening agent Substances 0.000 claims description 18
- 239000007822 coupling agent Substances 0.000 claims description 17
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 12
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims description 11
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 claims description 10
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 230000008878 coupling Effects 0.000 claims description 10
- 239000011777 magnesium Substances 0.000 claims description 10
- 238000010168 coupling process Methods 0.000 claims description 8
- 239000005055 methyl trichlorosilane Substances 0.000 claims description 7
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 230000000379 polymerizing effect Effects 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- 150000002681 magnesium compounds Chemical class 0.000 claims description 5
- 150000003752 zinc compounds Chemical class 0.000 claims description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical group Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims 2
- 239000000243 solution Substances 0.000 description 364
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 124
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 109
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 56
- 239000002904 solvent Substances 0.000 description 50
- 229920005669 high impact polystyrene Polymers 0.000 description 37
- 239000004797 high-impact polystyrene Substances 0.000 description 37
- 230000000052 comparative effect Effects 0.000 description 36
- 229920001971 elastomer Polymers 0.000 description 30
- 239000005060 rubber Substances 0.000 description 30
- 239000007789 gas Substances 0.000 description 27
- 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 description 26
- 239000005049 silicon tetrachloride Substances 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 238000001704 evaporation Methods 0.000 description 15
- 230000008020 evaporation Effects 0.000 description 14
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 12
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 12
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 11
- 239000004793 Polystyrene Substances 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 10
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- VCTCXZDCRFISFF-UHFFFAOYSA-N magnesium;butane;butane Chemical compound [Mg+2].CCC[CH2-].CC[CH-]C VCTCXZDCRFISFF-UHFFFAOYSA-N 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 239000011259 mixed solution Substances 0.000 description 10
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 10
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 10
- 229920002223 polystyrene Polymers 0.000 description 10
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 8
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 8
- 238000012662 bulk polymerization Methods 0.000 description 8
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 229910052744 lithium Inorganic materials 0.000 description 8
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 230000015271 coagulation Effects 0.000 description 7
- 238000005345 coagulation Methods 0.000 description 7
- 238000010998 test method Methods 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- FIYMNUNPPYABMU-UHFFFAOYSA-N 2-benzyl-5-chloro-1h-indole Chemical compound C=1C2=CC(Cl)=CC=C2NC=1CC1=CC=CC=C1 FIYMNUNPPYABMU-UHFFFAOYSA-N 0.000 description 6
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 235000019400 benzoyl peroxide Nutrition 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 229910052749 magnesium Inorganic materials 0.000 description 6
- 229910052759 nickel Inorganic materials 0.000 description 6
- 239000004014 plasticizer Substances 0.000 description 6
- 238000010526 radical polymerization reaction Methods 0.000 description 6
- 239000006228 supernatant Substances 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 235000011089 carbon dioxide Nutrition 0.000 description 4
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 4
- 239000002360 explosive Substances 0.000 description 4
- CCZVEWRRAVASGL-UHFFFAOYSA-N lithium;2-methanidylpropane Chemical compound [Li+].CC(C)[CH2-] CCZVEWRRAVASGL-UHFFFAOYSA-N 0.000 description 4
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 4
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910021645 metal ion Inorganic materials 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- HEPBQSXQJMTVFI-UHFFFAOYSA-N zinc;butane Chemical compound [Zn+2].CCC[CH2-].CCC[CH2-] HEPBQSXQJMTVFI-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 2
- VTPNYMSKBPZSTF-UHFFFAOYSA-N 1-ethenyl-2-ethylbenzene Chemical compound CCC1=CC=CC=C1C=C VTPNYMSKBPZSTF-UHFFFAOYSA-N 0.000 description 2
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 2
- XHUZSRRCICJJCN-UHFFFAOYSA-N 1-ethenyl-3-ethylbenzene Chemical compound CCC1=CC=CC(C=C)=C1 XHUZSRRCICJJCN-UHFFFAOYSA-N 0.000 description 2
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 2
- WHFHDVDXYKOSKI-UHFFFAOYSA-N 1-ethenyl-4-ethylbenzene Chemical compound CCC1=CC=C(C=C)C=C1 WHFHDVDXYKOSKI-UHFFFAOYSA-N 0.000 description 2
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
- XPVATDCOZDHQNL-UHFFFAOYSA-N CC(C)(C)[Mg]C(C)(C)C Chemical compound CC(C)(C)[Mg]C(C)(C)C XPVATDCOZDHQNL-UHFFFAOYSA-N 0.000 description 2
- RTAQCQOZRWKSTQ-UHFFFAOYSA-N CC(C)C[Mg]CC(C)C Chemical compound CC(C)C[Mg]CC(C)C RTAQCQOZRWKSTQ-UHFFFAOYSA-N 0.000 description 2
- DFLCBCMZFUSLNE-UHFFFAOYSA-N CC(C)C[Zn]CC(C)C Chemical compound CC(C)C[Zn]CC(C)C DFLCBCMZFUSLNE-UHFFFAOYSA-N 0.000 description 2
- SPXDYPYJHCSREL-UHFFFAOYSA-N CCC(C)[Mg]C(C)CC Chemical compound CCC(C)[Mg]C(C)CC SPXDYPYJHCSREL-UHFFFAOYSA-N 0.000 description 2
- YDNAWKQOSYKOSA-UHFFFAOYSA-N CCC(C)[Zn]C(C)CC Chemical compound CCC(C)[Zn]C(C)CC YDNAWKQOSYKOSA-UHFFFAOYSA-N 0.000 description 2
- QQTGJVBUIOTPGZ-UHFFFAOYSA-N CCC[Zn]CCC Chemical compound CCC[Zn]CCC QQTGJVBUIOTPGZ-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- QTANTQQOYSUMLC-UHFFFAOYSA-O Ethidium cation Chemical compound C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CC)=C1C1=CC=CC=C1 QTANTQQOYSUMLC-UHFFFAOYSA-O 0.000 description 2
- 241001441571 Hiodontidae Species 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- KYHHMFUFEIHUHB-UHFFFAOYSA-N di-tert-butylzinc Chemical compound CC(C)(C)[Zn]C(C)(C)C KYHHMFUFEIHUHB-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- QUBBAXISAHIDNM-UHFFFAOYSA-N ethyldimethylbenzene Natural products CCC1=CC=CC(C)=C1C QUBBAXISAHIDNM-UHFFFAOYSA-N 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 description 2
- XBEREOHJDYAKDA-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].CC[CH2-] XBEREOHJDYAKDA-UHFFFAOYSA-N 0.000 description 2
- KJJBSBKRXUVBMX-UHFFFAOYSA-N magnesium;butane Chemical compound [Mg+2].CCC[CH2-].CCC[CH2-] KJJBSBKRXUVBMX-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 230000003014 reinforcing effect Effects 0.000 description 2
- 238000005728 strengthening Methods 0.000 description 2
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- VALAJCQQJWINGW-UHFFFAOYSA-N tri(propan-2-yl)alumane Chemical compound CC(C)[Al](C(C)C)C(C)C VALAJCQQJWINGW-UHFFFAOYSA-N 0.000 description 2
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 2
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 2
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 2
- ZICNIEOYWVIEQJ-UHFFFAOYSA-N (2-methylbenzoyl) 2-methylbenzenecarboperoxoate Chemical compound CC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1C ZICNIEOYWVIEQJ-UHFFFAOYSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- FACXGONDLDSNOE-UHFFFAOYSA-N buta-1,3-diene;styrene Chemical compound C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 FACXGONDLDSNOE-UHFFFAOYSA-N 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 238000005453 pelletization Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
- C08F279/02—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00 on to polymers of conjugated dienes
- C08F279/04—Vinyl aromatic monomers and nitriles as the only monomers
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- C08F136/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F136/02—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F136/04—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F136/06—Butadiene
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
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- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
- C08F212/10—Styrene with nitriles
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- 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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- 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
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- C08L25/02—Homopolymers or copolymers of hydrocarbons
- C08L25/04—Homopolymers or copolymers of styrene
- C08L25/08—Copolymers of styrene
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- C08L47/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Compositions of derivatives of such polymers
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- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/04—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to rubbers
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- C08L55/00—Compositions of homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C08L23/00 - C08L53/00
- C08L55/02—ABS [Acrylonitrile-Butadiene-Styrene] polymers
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- C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
- C08F2500/03—Narrow molecular weight distribution, i.e. Mw/Mn < 3
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- C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
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| CN201710822652.7A CN109485791B (zh) | 2017-09-13 | 2017-09-13 | 线形丁苯共聚物及其制备方法和组合物以及芳族乙烯基树脂及其制备方法 |
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| KR102277132B1 (ko) * | 2019-12-03 | 2021-07-15 | 금호석유화학 주식회사 | 공중합체 및 그 제조방법 |
| CN111057190A (zh) * | 2019-12-11 | 2020-04-24 | 北方华锦化学工业股份有限公司 | 一种高光泽本体abs树脂的制备方法 |
| CN113621108B (zh) * | 2020-05-09 | 2024-09-17 | 中国石油化工股份有限公司 | 溶聚丁苯橡胶及其制备方法和应用 |
| CN113698558B (zh) * | 2020-05-20 | 2024-07-02 | 中国石油化工股份有限公司 | 丁苯共聚物及其制备方法与应用 |
| EP4029889A4 (de) * | 2020-07-08 | 2023-01-25 | LG Chem, Ltd. | Verfahren zur herstellung eines pfropfcopolymers und nach diesem verfahren hergestelltes pfropfcopolymer |
| CN114478917B (zh) * | 2020-10-23 | 2024-07-02 | 中国石油化工股份有限公司 | 丁苯橡胶及其制备方法和应用 |
| TW202330677A (zh) * | 2021-12-10 | 2023-08-01 | 義大利商佛沙里斯股份有限公司 | 橡膠強化的乙烯芳香族(共)聚合物及其製備方法 |
| CN114784282A (zh) * | 2022-05-26 | 2022-07-22 | 湖北亿纬动力有限公司 | 一种负极材料及其制备方法和应用 |
| CN114874389B (zh) * | 2022-06-14 | 2023-08-22 | 宁波新溶聚企业管理合伙企业(有限合伙) | 一种低引发剂残留的溶聚丁苯橡胶的生产方法及产品 |
| CN114957562A (zh) * | 2022-07-01 | 2022-08-30 | 北方华锦化学工业股份有限公司 | 一种高光泽高抗冲聚苯乙烯复合材料及制备方法 |
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| DE1694059C3 (de) | 1966-01-03 | 1974-02-28 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von mikroporösen, wasserdampfdurchlässigen Flächengebilden |
| ZA735903B (en) * | 1972-09-14 | 1974-07-31 | Uniroyal Inc | Solution diene elastomers by alkyl lithium catalysis |
| US4302568A (en) * | 1980-02-25 | 1981-11-24 | The General Tire & Rubber Co. | Solution polymerization |
| JPS5753507A (en) * | 1980-09-17 | 1982-03-30 | Asahi Chem Ind Co Ltd | Butadiene polymer and its preparation |
| JPH0621135B2 (ja) * | 1985-03-05 | 1994-03-23 | 電気化学工業株式会社 | ゴム変性スチレン系樹脂の製造方法 |
| JPH0794518B2 (ja) * | 1988-04-11 | 1995-10-11 | 旭化成工業株式会社 | 複合重合法 |
| JPH0234612A (ja) * | 1988-07-25 | 1990-02-05 | Nippon Porisuchiren Kogyo Kk | ゴム変性スチレン系樹脂 |
| US5274106A (en) * | 1991-12-30 | 1993-12-28 | Bridgestone Corporation | Amino-substituted aryllithium compounds as anionic polymerization initiators |
| ES2116199B1 (es) * | 1995-07-17 | 1999-04-01 | Repsol Quimica Sa | Procedimiento de preparacion de copolimeros de 1,3 butadieno y estireno utiles para la fabricacion de neumaticos con baja resistencia a la rodadura y copolimeros de 1,3-butadieno y estireno asi obtenidos, |
| US5807937A (en) * | 1995-11-15 | 1998-09-15 | Carnegie Mellon University | Processes based on atom (or group) transfer radical polymerization and novel (co) polymers having useful structures and properties |
| ES2178784T5 (es) * | 1996-08-19 | 2008-02-01 | Basf Aktiengesellschaft | Procedimiento para la polimerizacion anionica. |
| JP3603294B2 (ja) * | 1996-08-21 | 2004-12-22 | 日本ゼオン株式会社 | ポリブタジエンゴム及び耐衝撃性芳香族ビニル系樹脂組成物 |
| US5985997A (en) * | 1997-05-23 | 1999-11-16 | Chevron Chemical Company | In situ process for making a bimodal HIPS having both high gloss and high impact strength |
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| AU766724B2 (en) * | 1999-05-17 | 2003-10-23 | Styron Europe Gmbh | Bimodal rubbers and rubber modified high impact monovinylidene aromatic polymers produced therefrom |
| EP1423442B1 (de) * | 2001-07-16 | 2012-09-12 | Compagnie Generale Des Etablissements Michelin | Verfahren zur kontinuierlichen Herstellung von einem Dienelastomer mit cyclischen Vinyleinheiten |
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| KR100751020B1 (ko) * | 2005-12-29 | 2007-08-22 | 제일모직주식회사 | 내열특성과 표면광택도 및 실용충격강도가 우수한 고충격폴리스티렌 수지의 연속 제조방법 |
| US7321017B1 (en) * | 2006-08-24 | 2008-01-22 | The Goodyear Tire & Rubber Company | Amine containing catalyst system and methods of use thereof |
| US7396887B1 (en) * | 2006-12-29 | 2008-07-08 | Bridgestone Corporation | Insitu removal of chelator from anionic polymerization reactions |
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| TW201211083A (en) * | 2010-06-15 | 2012-03-16 | Styron Europe Gmbh | Low vinyl styrene-butadiene polymers and methods of making the same |
| EP2495266A1 (de) * | 2011-03-04 | 2012-09-05 | Styron Deutschland GmbH | Styrol-Butadien Kautschuk mit hohem Styrol- sowie hohem Vinyl-Gehalt und Herstellungsverfahren dafür |
| WO2012165038A1 (ja) | 2011-05-30 | 2012-12-06 | 住友ゴム工業株式会社 | トレッド用ゴム組成物及び空気入りタイヤ |
| EP2607381B1 (de) * | 2011-12-21 | 2018-01-24 | The Goodyear Tire & Rubber Company | Funktionalisierten elastomer, gummi zusammensetzung und reifen. |
| KR101555085B1 (ko) * | 2012-01-11 | 2015-09-23 | 금호석유화학 주식회사 | 스티렌-부타디엔 고무를 이용한 고무변성 스티렌계 수지의 연속 제조 방법 |
| CN103374102B (zh) * | 2012-04-20 | 2015-09-16 | 中国石油化工股份有限公司 | 1,3-共轭二烯烃/单乙烯基芳烃共聚物及其连续聚合的生产方法 |
| CN103467666A (zh) * | 2012-06-08 | 2013-12-25 | 上海华谊聚合物有限公司 | 一种制备高抗冲abs聚合物混合体的工艺 |
| CN102898584A (zh) * | 2012-10-09 | 2013-01-30 | 大连理工大学 | 苯乙烯-丁二烯-异戊二烯三元共聚物集成胶乳及其制备方法 |
| CN106589247B (zh) * | 2015-10-16 | 2018-12-28 | 中国石油化工股份有限公司 | 低顺式聚丁二烯橡胶及其制备方法和应用 |
| CN106699967B (zh) | 2015-11-13 | 2020-04-14 | 中国石油化工股份有限公司 | 一种采用钼系催化体系制备高乙烯基丁苯共聚物的方法 |
| CN109485772B (zh) * | 2017-09-13 | 2021-10-19 | 中国石油化工股份有限公司 | 低顺式聚丁二烯橡胶及其制备方法和组合物以及芳族乙烯基树脂及其制备方法 |
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| DE102017219342B4 (de) | 2021-01-21 |
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| JP2019052283A (ja) | 2019-04-04 |
| BE1025614A1 (de) | 2019-04-29 |
| DE102017219342A1 (de) | 2019-03-14 |
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