JP2013515162A - 改良されたビニル変性剤組成物および当該組成物の利用方法 - Google Patents
改良されたビニル変性剤組成物および当該組成物の利用方法 Download PDFInfo
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- JP2013515162A JP2013515162A JP2012546196A JP2012546196A JP2013515162A JP 2013515162 A JP2013515162 A JP 2013515162A JP 2012546196 A JP2012546196 A JP 2012546196A JP 2012546196 A JP2012546196 A JP 2012546196A JP 2013515162 A JP2013515162 A JP 2013515162A
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- butadiene
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- 239000000203 mixture Substances 0.000 title claims abstract description 90
- 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 74
- 238000000034 method Methods 0.000 title claims abstract description 65
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title claims abstract description 51
- 239000003607 modifier Substances 0.000 title abstract description 7
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 105
- -1 Oxolanyl compound Chemical class 0.000 claims abstract description 62
- 125000005475 oxolanyl group Chemical group 0.000 claims abstract description 13
- 229920000642 polymer Polymers 0.000 claims description 64
- 239000000178 monomer Substances 0.000 claims description 60
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 52
- 229920001400 block copolymer Polymers 0.000 claims description 44
- 150000001993 dienes Chemical class 0.000 claims description 38
- FZLHAQMQWDDWFI-UHFFFAOYSA-N 2-[2-(oxolan-2-yl)propan-2-yl]oxolane Chemical compound C1CCOC1C(C)(C)C1CCCO1 FZLHAQMQWDDWFI-UHFFFAOYSA-N 0.000 claims description 34
- 229920001577 copolymer Polymers 0.000 claims description 31
- 239000003999 initiator Substances 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 239000003153 chemical reaction reagent Substances 0.000 claims description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 8
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 230000000379 polymerizing effect Effects 0.000 claims description 7
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 claims description 6
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 claims description 4
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims description 4
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 claims description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001979 organolithium group Chemical group 0.000 claims description 2
- QTTAWIGVQMSWMV-UHFFFAOYSA-N 3,4-dimethylhexa-1,3-diene Chemical compound CCC(C)=C(C)C=C QTTAWIGVQMSWMV-UHFFFAOYSA-N 0.000 claims 2
- OCTVDLUSQOJZEK-UHFFFAOYSA-N 4,5-diethylocta-1,3-diene Chemical compound CCCC(CC)C(CC)=CC=C OCTVDLUSQOJZEK-UHFFFAOYSA-N 0.000 claims 2
- UGWOAPBVIGCNOV-UHFFFAOYSA-N 5-ethenyldec-5-ene Chemical compound CCCCC=C(C=C)CCCC UGWOAPBVIGCNOV-UHFFFAOYSA-N 0.000 claims 2
- XZKRXPZXQLARHH-UHFFFAOYSA-N buta-1,3-dienylbenzene Chemical compound C=CC=CC1=CC=CC=C1 XZKRXPZXQLARHH-UHFFFAOYSA-N 0.000 claims 2
- 150000002642 lithium compounds Chemical class 0.000 claims 1
- 125000002734 organomagnesium group Chemical group 0.000 claims 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
- 229920001971 elastomer Polymers 0.000 description 29
- 239000003795 chemical substances by application Substances 0.000 description 21
- 239000005060 rubber Substances 0.000 description 21
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 16
- 239000007822 coupling agent Substances 0.000 description 15
- 239000006229 carbon black Substances 0.000 description 12
- 235000019241 carbon black Nutrition 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000000377 silicon dioxide Substances 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 10
- 239000005062 Polybutadiene Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 229920002857 polybutadiene Polymers 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000004073 vulcanization Methods 0.000 description 8
- 239000004594 Masterbatch (MB) Substances 0.000 description 7
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 7
- 230000008878 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- 239000000945 filler Substances 0.000 description 7
- 125000000962 organic group Chemical group 0.000 description 7
- 229920006216 polyvinyl aromatic Polymers 0.000 description 7
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 7
- 229910052718 tin Inorganic materials 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- KFGFVPMRLOQXNB-UHFFFAOYSA-N 3,5,5-trimethylhexanoyl 3,5,5-trimethylhexaneperoxoate Chemical compound CC(C)(C)CC(C)CC(=O)OOC(=O)CC(C)CC(C)(C)C KFGFVPMRLOQXNB-UHFFFAOYSA-N 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- 125000000129 anionic group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000000806 elastomer Substances 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical class CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 239000006231 channel black Substances 0.000 description 4
- 229910001507 metal halide Inorganic materials 0.000 description 4
- 150000004040 pyrrolidinones Chemical class 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical class Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 3
- 238000002679 ablation Methods 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052732 germanium Inorganic materials 0.000 description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 229910052752 metalloid Inorganic materials 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 150000002900 organolithium compounds Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- 238000010058 rubber compounding Methods 0.000 description 3
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229920003051 synthetic elastomer Polymers 0.000 description 3
- 150000003555 thioacetals Chemical class 0.000 description 3
- LLVWLCAZSOLOTF-UHFFFAOYSA-N 1-methyl-4-[1,4,4-tris(4-methylphenyl)buta-1,3-dienyl]benzene Chemical compound C1=CC(C)=CC=C1C(C=1C=CC(C)=CC=1)=CC=C(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 LLVWLCAZSOLOTF-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical class C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CJSBUWDGPXGFGA-UHFFFAOYSA-N 4-methylpenta-1,3-diene Chemical compound CC(C)=CC=C CJSBUWDGPXGFGA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 239000006057 Non-nutritive feed additive Substances 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
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- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
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- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- FQEKAFQSVPLXON-UHFFFAOYSA-N butyl(trichloro)silane Chemical compound CCCC[Si](Cl)(Cl)Cl FQEKAFQSVPLXON-UHFFFAOYSA-N 0.000 description 2
- YMLFYGFCXGNERH-UHFFFAOYSA-K butyltin trichloride Chemical compound CCCC[Sn](Cl)(Cl)Cl YMLFYGFCXGNERH-UHFFFAOYSA-K 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
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- 238000005516 engineering process Methods 0.000 description 2
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- 125000005843 halogen group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 150000002483 hydrogen compounds Chemical class 0.000 description 2
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000005055 methyl trichlorosilane Substances 0.000 description 2
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
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- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 description 1
- BOGRNZQRTNVZCZ-AATRIKPKSA-N (3e)-3-methylpenta-1,3-diene Chemical compound C\C=C(/C)C=C BOGRNZQRTNVZCZ-AATRIKPKSA-N 0.000 description 1
- BOGRNZQRTNVZCZ-UHFFFAOYSA-N 1,2-dimethyl-butadiene Natural products CC=C(C)C=C BOGRNZQRTNVZCZ-UHFFFAOYSA-N 0.000 description 1
- CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical compound C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 description 1
- CBXRMKZFYQISIV-UHFFFAOYSA-N 1-n,1-n,1-n',1-n',2-n,2-n,2-n',2-n'-octamethylethene-1,1,2,2-tetramine Chemical compound CN(C)C(N(C)C)=C(N(C)C)N(C)C CBXRMKZFYQISIV-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
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- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- IGLWCQMNTGCUBB-UHFFFAOYSA-N 3-methylidenepent-1-ene Chemical compound CCC(=C)C=C IGLWCQMNTGCUBB-UHFFFAOYSA-N 0.000 description 1
- YJRQBOOMJGYUPI-UHFFFAOYSA-N 4-methyl-2,3-dihydro-1,4-benzoxazine Chemical compound C1=CC=C2N(C)CCOC2=C1 YJRQBOOMJGYUPI-UHFFFAOYSA-N 0.000 description 1
- ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical class OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 description 1
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
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- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
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- 229910021623 Tin(IV) bromide Inorganic materials 0.000 description 1
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- CHWQTJXSOADSSD-UHFFFAOYSA-N [Li]C1(C(C=CC=C1)C1SCCCS1)N1CCN(CC1)C Chemical compound [Li]C1(C(C=CC=C1)C1SCCCS1)N1CCN(CC1)C CHWQTJXSOADSSD-UHFFFAOYSA-N 0.000 description 1
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Images
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- 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
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/12—Radicals substituted by oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- 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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- 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
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- 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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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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Abstract
Description
本開示は、特定の構造の1種以上のオキソラニル化合物のメソ−異性体を特定量含むオキソラニル化合物含有組成物と、重合方法におけるビニル含有量変性剤としての斯かる組成物の使用とに関する。そのメソ−異性体が、市販されて従来より用いられていたD体、L体およびメソ体の混合物よりも、重合反応においてビニル含有量変性剤として用いられた際に、より活性であることが、予想外に見出された。そのメソ−異性体の向上した活性により、比較的少ないオキソラニル化合物の使用で、市販されているD形、L形およびメソ体の異性体の混合物と同じ結果を達成できる。2,2−ジ(2−テトラヒドロフリル)プロパン等のオキソラニル化合物の市販されている組成物は、約50%(すなわち、50%+/−1%)のD形,L形異性体と、約50%(すなわち、50%+/−1%)のメソ異性体との混合物を含む。
α−V−D−ω’・・・(I)
式中、Vは、ポリビニル芳香族ブロックであり、Dは、ポリジエンブロックであり、αとω’は、各々独立して、水素原子、官能基、または重合セグメントもしくは重合ブロックであり、Dは、少なくとも50%のビニル含有量により特徴づけられる。
d−V−D−ω’
式中、dは、ジエンモノマーの重合から誘導されるポリジエンブロックであり、V、Dおよびω’は、式Iに関する上記規定と同様であり、Dおよびdは、少なくとも50%のビニル含有量により特徴づけられる。
α−Vo−D−V'−ω’
式中、各Vは、独立して、ポリビニル芳香族ブロックであり、Dは、ポリジエンブロックであり、αとω’は、各々独立して、水素原子、官能基、または重合セグメントもしくは重合ブロックであり、Dは、少なくとも50%のビニル含有量により特徴づけられる。
d−Vo−D−V'−ω’
式中、dは、ポリジエンブロックであり、Vo、V'、D、およびω’は、式IIIに関する上記規定と同様であり、Dおよびdは、少なくとも50%のビニル含有量により特徴づけられる。
1,3−ブタジエン、イソプレン、1,3−ペンタジエン、1,3−ヘキサジエン、2,3−ジメチル−1,3−ブタジエン、2−エチル−1,3−ブタジエン、2−メチル−1,3−ペンタジエン、3−メチル−1,3−ペンタジエン、4−メチル−1,3−ペンタジエン、および2,4−ヘキサジエンを含む。2種以上の共役ジエンの混合物を共重合に用いてもよい。好適な共役ジエンは、1,3−ブタジエン、イソプレン、1,3−ペンタジエン、および1,3−ヘキサジエンである。
商業的に得られる量の2,2−ジ(2−テトラヒドロフリル)プロパン(Penn Specialty Chemicals)をカラムクロマトグラフィーを用いて精製し、ジアステレオ異性体を単離した。230〜400メッシュサイズのシリカゲル(Fisher Scientificから入手可能)固定相と、20%ジエチルエーテルおよび80%n−ペンタンの移動相とを具えるカラムを準備した。25mL反復量の移動相を用いた。純粋なメソ−2,2−ジ(2−テトラヒドロフリル)プロパンが、第一留分として単離された。そのメソ−異性体の収率は、2,2−ジ(2−テトラヒドロフリル)プロパンの元の量の約20%だった。純粋なD,L−2,2−ジ(2−テトラヒドロフリル)プロパンが第二留分として単離され、その収率も2,2−ジ(2−テトラヒドロフリル)プロパンの元の量の約20%だった。出発時の2,2−ジ(2−テトラヒドロフリル)プロパンと2つのジアステレオ異性体のGC−FID分析が、初めの2つの留分の純度を確認した。条件は以下のとおりである:SupelcoのEquity 1 column(30m×0.32mm×5.0μm)を使用;GC−インジェクションポート温度:260℃;インジェクションポート分割比:20:1;キャリアガスを1.5mL/分のコンスタントフローモードで流した;FID温度:280℃;サンプルサイズ:1μL。
カラムオーブンプログラム:
クリンプシールキャップを具えた窒素パージした800mLの容器に、ヘキサン中の1,3−ブタジエン21.8重量%(183.5g)、ヘキサン中のn−ブチルリチウム1.65Mを0.24mL、および、種々のメソ、DLまたは市販されている2,2−ジ(2−テトラヒドロフリル)プロパン(51重量%のメソ異性体と約49重量%のDおよびL異性体とを含有、以下「混合物」という)の種々の量(以下の表1)を加えた。その容器を50℃の湯浴に4時間置いた。2,2−ジ(2−テトラヒドロフリル)プロパン(「DTHFP」)の濃度をGCにより測定し、ビニル含有量を1H−NMRにより測定し、そして分子量を適切なMark−Houwink定数を用いたGPC(ポリスチレン標準)により測定した。
クリンプシールキャップを具えた窒素パージした800mLの容器に、ヘキサン中のスチレン34重量%を23.5g、ヘキサン中の1,3−ブタジエン22.3重量%を14.35g、ヘキサン中のn−ブチルリチウム1.65Mを0.24mL、および種々のメソ(メソ100%)、純粋なDL(DL100%)または市販されている2,2−ジ(2−テトラヒドロフリル)プロパン(約50重量%のメソ異性体と約50重量%のDおよびL異性体とを含有、以下「混合物」という)の種々の量(以下の表2)を加えた。その容器を50℃の湯浴に4時間置いた。2,2−ジ(2−テトラヒドロフリル)プロパンの濃度をGCにより測定し、ビニル含有量を1H−NMRにより測定し、そして分子量を適切なMark−Houwink定数を用いたGPC(ポリスチレン標準)により測定した。
窒素パージした800mLの容器に、ヘキサン214gおよびヘキサン中の21.5重量%のブタジエン186gを加えた。次いで、種々のメソ濃度(99.8%、88.1%、87.3%、75%、65.3%、54.9%、44.9%、そして5.8%)の約0.4Mの2,2−ジテトラヒドロフリルプロパンの0.08mL、0.15mL、0.30mL、0.60mLまたは1.0mLのいずれかを加えた。その後、ヘキサン中のn−ブチルリチウム1.65Mを0.24mL加え、その容器を50℃まで4時間加熱した。ポリブタジエンサンプル中のビニル含有量を測定するために1H−NMRを用いて、2,2−ジテトラヒドロフリルプロパンの濃度を測定するためにGCを用いた。
次に、アニオン性ブタジエン重合の速度を、99.8%のメソ2,2−ジテトラヒドロフリルプロパンと49.7%のメソ2,2−ジテトラヒドロフリルプロパンの存在下における改良された重合について調査した。
窒素パージした7.57Lのステンレス鋼反応器に無水ヘキサン0.54kgおよびヘキサン中の20.9重量%の1,3−ブタジエン1.63kgを加えた。次いで、0.36Mの2,2−ジテトラヒドロフリルプロパン(メソ99.8%)5.73mLおよびヘキサン中の1.65Mのブチルリチウム1.37mLを11.7℃で加えた。(上述したカラムクロマトグラフィー方法を用いてメソ99.8%の2,2−ジテトラヒドロフリルプロパンが単離された)反応器のジャケットを71.1℃に設定した。5,10,15,20,25,30,45,60,および90分におけるサンプルを採取し、変換率および分子量を測定した。20,30および60分におけるサンプルについて1H−NMRによりビニル含有量を調べた。GCを用いて、反応における1,3−ブタジエンおよび2,2−ジテトラヒドロフリルプロパン(124ppm)の濃度を測定した。
窒素パージした7.57Lのステンレス鋼反応器に無水ヘキサン0.54kgおよびヘキサン中の20.9重量%の1,3−ブタジエン1.63kgを加えた。次いで、1.6Mの2,2−ジテトラヒドロフリルプロパン(メソ49.7%)0.82mLおよびヘキサン中の1.65Mのブチルリチウム1.37mLを12.1℃で加えた。(供給業者から受領したメソ49.7%の2,2−ジテトラヒドロフリルプロパンを用いた。)反応器のジャケットを71.1℃に設定した。5,10,15,20,25,30,45,60,および90分におけるサンプルを採取し、重合率および分子量を測定した。20,30および60分におけるサンプルについて1H−NMRによりビニル含有量を調べた。GCを用いて、反応における1,3−ブタジエンおよび2,2−ジテトラヒドロフリルプロパン(176ppm)の濃度を測定した。
Claims (25)
- 前記メソ−異性体が、少なくとも1種のオキソラニル化合物の少なくとも60重量%を含む、請求項1に記載の組成物。
- 前記メソ−異性体が、少なくとも1種のオキソラニル化合物の少なくとも90重量%を含む、請求項1に記載の組成物。
- 前記オキソラニル化合物が、2,2−ジ(2−テトラヒドロフリル)プロパンを含む、請求項1に記載の組成物。
- 前記組成物が、精製された混合物である、請求項1に記載の組成物。
- 前記メソ−異性体が、前記組成物の少なくとも60重量%ある、請求項6に記載の方法。
- 前記メソ−異性体が、前記組成物の少なくとも90重量%ある、請求項6に記載の方法。
- 前記オキソラニル化合物が、2,2−ジ(2−テトラヒドロフリル)プロパンを含む、請求項6に記載の方法。
- 前記メソ−異性体が、前記組成物の少なくとも90重量%ある、請求項9に記載の方法。
- 少なくとも1種のビニル芳香族モノマーの重合工程をさらに含む、請求項6に記載の方法。
- 前記少なくとも1種のビニル芳香族モノマーが、スチレン、α−メチルスチレン、p−メチルスチレン、ビニルナフタレン、およびそれらの混合物からなる群より選択される、請求項11に記載の方法。
- 前記少なくとも1種の共役ジエンモノマーが、1,3−ブタジエン、イソプレン、1,3−ペンタジエン、2,3−ジメチル−1,3−ブタジエン、1,3−ヘキサジエン、2−メチル−1,3−ペンタジエン、3,4−ジメチル−1,3−ヘキサジエン、4,5−ジエチル−1,3−オクタジエン、3−ブチル−1,3−オクタジエン、フェニル−1,3−ブタジエン、およびそれらの混合物からなる群より選択される、請求項11に記載の方法。
- 結果物のポリジエン重合体が、10%以上100%未満のビニル含有量を有するブロック共重合体である、請求項11に記載の方法。
- 少なくとも1種の有機金属アニオン性開始剤の使用をさらに含む、請求項6に記載の方法。
- 前記少なくとも1種の有機金属アニオン性開始剤が、有機リチウム、有機マグネシウム、有機ナトリウム、有機カリウム、トリ有機スズリチウム化合物、およびそれらの混合物からなる群より選択される、請求項15に記載の方法。
- 少なくとも1種の停止試薬の使用をさらに含む、請求項6に記載の方法。
- 前記少なくとも1種の共役ジエンモノマーが、1,3−ブタジエン、イソプレン、1,3−ペンタジエン、2,3−ジメチル−1,3−ブタジエン、1,3−ヘキサジエン、2−メチル−1,3−ペンタジエン、3,4−ジメチル−1,3−ヘキサジエン、4,5−ジエチル−1,3−オクタジエン、3−ブチル−1,3−オクタジエン、フェニル−1,3−ブタジエン、およびそれらの混合物からなる群より選択される、請求項6に記載の方法。
- 前記メソ−異性体の前記有機金属アニオン性開始剤に対するモル比が、0.001:1〜1:1である、請求項6に記載の方法。
- 請求項6に記載の方法により調製される、ポリジエン重合体または共重合体。
- 請求項6に記載の方法により調製されるポリジエン重合体または共重合体を含む、タイヤ製品。
- オキソラニル化合物2,2−ジ(2−テトラヒドロフリル)プロパンの存在下、1,3−ブタジエンを重合する工程を含む重合方法であって、前記オキソラニル化合物が、少なくとも52重量%のメソ−異性体を含み、
前記方法が、10〜65%のビニル含有量を有するポリジエン重合体を製造し、
前記方法が、有機リチウムアニオン性開始剤の使用を含み、かつ
前記重合方法が、ピーク重合温度が85℃〜120℃で行われる、重合方法。 - 前記方法が、スチレンと1,3−ブタジエンとを重合し、共重合体を製造する工程をさらに含む、請求項22に記載の重合方法。
- 少なくとも1種の停止試薬の使用をさらに含む、請求項22に記載の重合方法。
- 請求項22に記載の方法により調製されるポリジエン重合体または共重合体を含む、タイヤ製品。
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US9309330B2 (en) | 2016-04-12 |
US20160237181A1 (en) | 2016-08-18 |
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US20120259082A1 (en) | 2012-10-11 |
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JP2015017258A (ja) | 2015-01-29 |
EP2516410B1 (en) | 2014-04-23 |
KR101890097B1 (ko) | 2018-08-20 |
BR112012015120B1 (pt) | 2020-07-21 |
US20180134815A1 (en) | 2018-05-17 |
EP2516410A1 (en) | 2012-10-31 |
KR20180019769A (ko) | 2018-02-26 |
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KR20120106851A (ko) | 2012-09-26 |
KR101830872B1 (ko) | 2018-02-26 |
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CN102770418A (zh) | 2012-11-07 |
US10723817B2 (en) | 2020-07-28 |
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