JP5718543B2 - 機能化したゴム状重合体 - Google Patents
機能化したゴム状重合体 Download PDFInfo
- Publication number
- JP5718543B2 JP5718543B2 JP2006318745A JP2006318745A JP5718543B2 JP 5718543 B2 JP5718543 B2 JP 5718543B2 JP 2006318745 A JP2006318745 A JP 2006318745A JP 2006318745 A JP2006318745 A JP 2006318745A JP 5718543 B2 JP5718543 B2 JP 5718543B2
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen atom
- alkyl group
- carbon atoms
- monomer
- polymerization
- 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.)
- Expired - Fee Related
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- 229920001971 elastomer Polymers 0.000 title claims description 85
- 239000000178 monomer Substances 0.000 claims description 145
- 125000004432 carbon atom Chemical group C* 0.000 claims description 74
- 125000000217 alkyl group Chemical group 0.000 claims description 71
- 238000006116 polymerization reaction Methods 0.000 claims description 65
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 64
- 239000000203 mixture Substances 0.000 claims description 63
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 48
- 229920000642 polymer Polymers 0.000 claims description 38
- 150000001993 dienes Chemical class 0.000 claims description 37
- 239000003999 initiator Substances 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 37
- 239000007822 coupling agent Substances 0.000 claims description 36
- 239000006229 carbon black Substances 0.000 claims description 27
- 239000000377 silicon dioxide Substances 0.000 claims description 24
- 239000000945 filler Substances 0.000 claims description 14
- 239000011324 bead Substances 0.000 claims description 9
- 150000003254 radicals Chemical class 0.000 claims description 9
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 6
- 230000000379 polymerizing effect Effects 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 230000002194 synthesizing effect Effects 0.000 claims description 4
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 3
- 235000012489 doughnuts Nutrition 0.000 claims 1
- -1 heterocyclic aromatic nitrogen-containing compound Chemical class 0.000 description 55
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 53
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 41
- 239000005060 rubber Substances 0.000 description 32
- 229910052744 lithium Inorganic materials 0.000 description 29
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 28
- 235000019241 carbon black Nutrition 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 229910052710 silicon Inorganic materials 0.000 description 21
- 239000010703 silicon Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 229920002554 vinyl polymer Polymers 0.000 description 19
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 16
- 229910052751 metal Inorganic materials 0.000 description 16
- 239000002184 metal Substances 0.000 description 16
- 150000003839 salts Chemical class 0.000 description 14
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 13
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 13
- 125000002947 alkylene group Chemical group 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 229910052708 sodium Inorganic materials 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 125000004122 cyclic group Chemical group 0.000 description 12
- 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 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 239000003607 modifier Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 229910052783 alkali metal Inorganic materials 0.000 description 10
- 125000000129 anionic group Chemical group 0.000 description 10
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- 229910052700 potassium Inorganic materials 0.000 description 9
- FXWRUNXMOLCZEE-UHFFFAOYSA-N 2-(4-ethenylphenyl)ethanamine Chemical compound NCCC1=CC=C(C=C)C=C1 FXWRUNXMOLCZEE-UHFFFAOYSA-N 0.000 description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 239000011591 potassium Substances 0.000 description 8
- KOYRSFAGDDMDTH-UHFFFAOYSA-N 2-(3-ethenylphenyl)ethanamine Chemical compound NCCC1=CC=CC(C=C)=C1 KOYRSFAGDDMDTH-UHFFFAOYSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 229920003051 synthetic elastomer Polymers 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- 239000005062 Polybutadiene Substances 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical class [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 6
- 229920002857 polybutadiene Polymers 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 229920003048 styrene butadiene rubber Polymers 0.000 description 6
- 239000005061 synthetic rubber Substances 0.000 description 6
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 238000011068 loading method Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 239000011414 polymer cement Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 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 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- 229920005683 SIBR Polymers 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000006231 channel black Substances 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification 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
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 239000011954 Ziegler–Natta catalyst Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 3
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000002738 chelating agent Substances 0.000 description 3
- 230000015271 coagulation Effects 0.000 description 3
- 238000005345 coagulation Methods 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 239000002563 ionic surfactant Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-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
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 239000006238 High Abrasion Furnace Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-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
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 229920000459 Nitrile rubber Polymers 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000006236 Super Abrasion Furnace Substances 0.000 description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000006294 amino alkylene group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 125000002993 cycloalkylene group Chemical group 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical class OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- DLAHAXOYRFRPFQ-UHFFFAOYSA-N dodecyl benzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=CC=C1 DLAHAXOYRFRPFQ-UHFFFAOYSA-N 0.000 description 2
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000002432 hydroperoxides Chemical class 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 229920003049 isoprene rubber Polymers 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 150000002641 lithium Chemical group 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 150000002900 organolithium compounds Chemical class 0.000 description 2
- 125000005702 oxyalkylene group Chemical group 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- DOHQKCXFKFANER-UHFFFAOYSA-M potassium;2-methoxyphenolate Chemical compound [K+].COC1=CC=CC=C1[O-] DOHQKCXFKFANER-UHFFFAOYSA-M 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 150000004040 pyrrolidinones Chemical class 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 229910052701 rubidium Inorganic materials 0.000 description 2
- 239000005049 silicon tetrachloride Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- QPBYLOWPSRZOFX-UHFFFAOYSA-J tin(iv) iodide Chemical compound I[Sn](I)(I)I QPBYLOWPSRZOFX-UHFFFAOYSA-J 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- MGAXYKDBRBNWKT-UHFFFAOYSA-N (5-oxooxolan-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC(=O)CC1 MGAXYKDBRBNWKT-UHFFFAOYSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- UWTUEMKLYAGTNQ-OWOJBTEDSA-N (e)-1,2-dibromoethene Chemical compound Br\C=C\Br UWTUEMKLYAGTNQ-OWOJBTEDSA-N 0.000 description 1
- LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical compound ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 description 1
- HIACAHMKXQESOV-UHFFFAOYSA-N 1,2-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC=C1C(C)=C HIACAHMKXQESOV-UHFFFAOYSA-N 0.000 description 1
- KFUSEUYYWQURPO-UHFFFAOYSA-N 1,2-dichloroethene Chemical compound ClC=CCl KFUSEUYYWQURPO-UHFFFAOYSA-N 0.000 description 1
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- 230000000737 periodic effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- LWDIVQRCGZJURD-UHFFFAOYSA-M potassium;2-ethoxyphenolate Chemical compound [K+].CCOC1=CC=CC=C1[O-] LWDIVQRCGZJURD-UHFFFAOYSA-M 0.000 description 1
- FDOIUSSCASVIGM-UHFFFAOYSA-N potassium;2-methylbutan-2-ol Chemical compound [K+].CCC(C)(C)O FDOIUSSCASVIGM-UHFFFAOYSA-N 0.000 description 1
- QYOPKBHBMWMNAO-UHFFFAOYSA-N potassium;2-methylpentan-2-olate Chemical compound [K+].CCCC(C)(C)[O-] QYOPKBHBMWMNAO-UHFFFAOYSA-N 0.000 description 1
- DMERGXDBCIXRCA-UHFFFAOYSA-N potassium;3-methylbutan-2-olate Chemical compound [K+].CC(C)C(C)[O-] DMERGXDBCIXRCA-UHFFFAOYSA-N 0.000 description 1
- QIBTYXXMIVLDLM-UHFFFAOYSA-M potassium;4-dodecylphenolate Chemical compound [K+].CCCCCCCCCCCCC1=CC=C([O-])C=C1 QIBTYXXMIVLDLM-UHFFFAOYSA-M 0.000 description 1
- NOCQQZLSUGMTIS-UHFFFAOYSA-M potassium;4-methoxyphenolate Chemical compound [K+].COC1=CC=C([O-])C=C1 NOCQQZLSUGMTIS-UHFFFAOYSA-M 0.000 description 1
- RRAHCFJFWDVGGZ-UHFFFAOYSA-M potassium;4-methylphenolate Chemical compound [K+].CC1=CC=C([O-])C=C1 RRAHCFJFWDVGGZ-UHFFFAOYSA-M 0.000 description 1
- LCKGXHKATMVYGO-UHFFFAOYSA-M potassium;4-nonylphenolate Chemical compound [K+].CCCCCCCCCC1=CC=C([O-])C=C1 LCKGXHKATMVYGO-UHFFFAOYSA-M 0.000 description 1
- KXPNDAJGKXDUDY-UHFFFAOYSA-M potassium;4-octylphenolate Chemical compound [K+].CCCCCCCCC1=CC=C([O-])C=C1 KXPNDAJGKXDUDY-UHFFFAOYSA-M 0.000 description 1
- ZUPDNLCLXSWMAE-UHFFFAOYSA-N potassium;butan-2-olate Chemical compound [K+].CCC(C)[O-] ZUPDNLCLXSWMAE-UHFFFAOYSA-N 0.000 description 1
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000012673 precipitation polymerization Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 238000010074 rubber mixing Methods 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- AIFMYMZGQVTROK-UHFFFAOYSA-N silicon tetrabromide Chemical compound Br[Si](Br)(Br)Br AIFMYMZGQVTROK-UHFFFAOYSA-N 0.000 description 1
- ABTOQLMXBSRXSM-UHFFFAOYSA-N silicon tetrafluoride Chemical compound F[Si](F)(F)F ABTOQLMXBSRXSM-UHFFFAOYSA-N 0.000 description 1
- JHGCXUUFRJCMON-UHFFFAOYSA-J silicon(4+);tetraiodide Chemical compound [Si+4].[I-].[I-].[I-].[I-] JHGCXUUFRJCMON-UHFFFAOYSA-J 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- MLUSGSAOOAWMFU-UHFFFAOYSA-M sodium;2-ethoxyphenolate Chemical compound [Na+].CCOC1=CC=CC=C1[O-] MLUSGSAOOAWMFU-UHFFFAOYSA-M 0.000 description 1
- QATMABZDQQPJGE-UHFFFAOYSA-M sodium;2-methoxyphenolate Chemical compound [Na+].COC1=CC=CC=C1[O-] QATMABZDQQPJGE-UHFFFAOYSA-M 0.000 description 1
- CGRKYEALWSRNJS-UHFFFAOYSA-N sodium;2-methylbutan-2-olate Chemical compound [Na+].CCC(C)(C)[O-] CGRKYEALWSRNJS-UHFFFAOYSA-N 0.000 description 1
- NOBCJNBWINPTEJ-UHFFFAOYSA-N sodium;2-methylpentan-2-olate Chemical compound CCCC(C)(C)O[Na] NOBCJNBWINPTEJ-UHFFFAOYSA-N 0.000 description 1
- IJXIZPHVQAOCSM-UHFFFAOYSA-N sodium;3-methylbutan-2-olate Chemical compound [Na+].CC(C)C(C)[O-] IJXIZPHVQAOCSM-UHFFFAOYSA-N 0.000 description 1
- GUSLDHIGLVOREE-UHFFFAOYSA-M sodium;4-dodecylphenolate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=C([O-])C=C1 GUSLDHIGLVOREE-UHFFFAOYSA-M 0.000 description 1
- MYMOTVMHKLYQCM-UHFFFAOYSA-M sodium;4-methoxyphenolate Chemical compound [Na+].COC1=CC=C([O-])C=C1 MYMOTVMHKLYQCM-UHFFFAOYSA-M 0.000 description 1
- ZECBPBHBGNLLMU-UHFFFAOYSA-M sodium;4-methylphenolate Chemical compound [Na+].CC1=CC=C([O-])C=C1 ZECBPBHBGNLLMU-UHFFFAOYSA-M 0.000 description 1
- GRHLOHHSYRUYNE-UHFFFAOYSA-M sodium;4-nonylphenolate Chemical compound [Na+].CCCCCCCCCC1=CC=C([O-])C=C1 GRHLOHHSYRUYNE-UHFFFAOYSA-M 0.000 description 1
- ITBBQYJVKRRIEE-UHFFFAOYSA-M sodium;4-octylphenolate Chemical compound [Na+].CCCCCCCCC1=CC=C([O-])C=C1 ITBBQYJVKRRIEE-UHFFFAOYSA-M 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- VSCLJRSWEGZJNY-UHFFFAOYSA-N sodium;butan-2-olate Chemical compound [Na+].CCC(C)[O-] VSCLJRSWEGZJNY-UHFFFAOYSA-N 0.000 description 1
- AJXVJQAPXVDFBT-UHFFFAOYSA-M sodium;naphthalen-2-olate Chemical compound [Na+].C1=CC=CC2=CC([O-])=CC=C21 AJXVJQAPXVDFBT-UHFFFAOYSA-M 0.000 description 1
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 1
- YUOWTJMRMWQJDA-UHFFFAOYSA-J tin(iv) fluoride Chemical compound [F-].[F-].[F-].[F-].[Sn+4] YUOWTJMRMWQJDA-UHFFFAOYSA-J 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
Classifications
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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
- 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
- C08F236/12—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 nitriles
-
- 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
- B60C1/0016—Compositions of the tread
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
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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
- 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
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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
- C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
- C08F212/26—Nitrogen
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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
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Description
タイヤ、ホース、伝動ベルトおよびその他の工業製品において用いられるゴム状重合体については、カーボンブラックやシリカなどの充填剤と良好な相溶性を有することが重要である。充填剤との改善された相互作用を得るために、そのようなゴム状重合体は、アミンなどの様々な化合物で機能化することができる。米国特許第4,935,471号は、カーボンブラックに対して高いレベルの親和性を有するポリジエンを調製するための方法を開示し、この方法は、金属を末端基とするポリジエンを、(a)構造式X-A-C≡Nを有するハロゲン化ニトリル(ここでXはハロゲン原子を表わし、Aは1〜20の炭素原子を含むアルキレン基を表わす)、(b)複素環式芳香族窒素含有化合物、および(c)アルキルベンゾエート、からなる群から選択されるキャッピング剤(capping agent)と反応させることを含む。米国特許第4,935,471号で開示されたキャッピング剤は金属を末端基とするポリジエンと反応し、そしてその金属を、末端のシアン化物基、複素環式芳香族窒素含有基またはアルキルベンゾエートから誘導される末端基と置換させる。例えば、金属を末端基とするポリジエンがニトリルでキャップ(cap)されると、シアン化物基が末端となったポリジエン鎖が生じるだろう。複素環式芳香族窒素含有化合物をキャッピング剤として使用すると、ピロリル基、イミダゾリル基、ピラゾリル基、ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、インドリジニル基、イソインドリル基、3-H-インドリル基、シノリニル基、ピリジニル基、ベータ-カルボリニル基、ペリミジニル基、フェナントロリニル基、またはその種の他のものが末端となったポリジエン鎖が生じうる。
合成ゴムについては、低いレベルのヒステリシスを示すことも望ましい。このことは、タイヤトレッド化合物で用いられるゴムの場合に特に重要である。そのような重合体は通常、硫黄、カーボンブラック、促進剤、分解防止剤およびその他の所望のゴム薬品と配合され、続いて有用な物品の形状に加硫または硬化される。そのような硬化したゴムの物理的特性は、カーボンブラックがポリジエンゴムの全体にわたって均質に分散している度合いに依存する、ということが確立されている。このことはひいては、ゴムに対してカーボンブラックが有する親和性のレベルに関係する。このことは、ポリジエンゴムを利用して製造されるゴム製品の物理的性質を改善する際に、実際に重要になることがある。例えば、タイヤの回転抵抗性とトレッドの摩耗特性は、カーボンブラックが中に添加されているゴム状重合体に対するそのカーボンブラックの親和性を増大させることによって改善されうる。従って、カーボンブラックおよび/またはシリカに対する所定のポリジエンゴムの親和性を改善することが、非常に望ましいであろう。というのは、タイヤトレッド組成物を配合するのに用いられるポリジエンゴムの全体にわたってカーボンブラックの分散性が良好であれば、より低いヒステリシス値が得られ、その結果、その組成物から製造されるタイヤは低い回転抵抗を有するからである。また、ヒステリシスの主な原因は、十分に弾性回復をすることのできないポリマー鎖の末端によるものである、ということも知られている。従って、充填剤に対するゴム鎖の末端の親和性を改善することが、ヒステリシスを低減させるのに非常に重要である。
発明の概要
本発明は、低いヒステリシスおよびカーボンブラックやシリカなどの充填剤との良好な相溶性を有するゴム状重合体に重合させることのできる機能化した単量体に関する。本発明の機能化した単量体は典型的に、1以上の共役ジオレフィン単量体および場合によってビニル芳香族単量体などの共重合性の他の単量体と共重合させることによって、ゴム状重合体に組み込まれる。いずれの場合であっても、本発明の機能化した単量体はカーボンブラックやシリカなどのゴムコンパウンドにおいて典型的に用いられるタイプの充填剤とのゴムの相溶性を改善するので、重合体の特性が改善されることが認められる。
本発明の機能化した単量体は、共重合させて実質的にあらゆるタイプの合成ゴムにすることができる。たいていの場合、その機能化した単量体は、少なくとも一つの共役ジオレフィン単量体と共重合するだろう。場合によって、共役ジオレフィン単量体と共重合しうるビニル芳香族単量体などの他の単量体も、重合に組み込むことができる。いずれの場合であっても、典型的に約0.1phm(100重量部の単量体当りの重量部)から約100phmまでの機能化した単量体が、重合に組み込まれるだろう。より典型的には、約0.05phmから約10phmまでの機能化した単量体が、ゴム状重合体に含まれるだろう。良好な結果は通常、0.1phm〜5phmの機能化した単量体をゴム状重合体中に含めることによって得られる。最も典型的には、機能化した単量体はゴム状重合体に0.5phm〜2phmの範囲内の量で組み込まれるだろう。
本発明に従う重合反応は、反応条件の下で液体であって比較的不活性な適当な溶剤中で実施することができる。溶剤はジエン反応物質と同数の1分子当りの炭素原子を有していてもよく、あるいはそれは異なる沸点範囲のものであってもよい。好ましい溶剤はアルカン炭化水素およびシクロアルカン炭化水素である。適当な溶剤は例えば、ヘキサン、シクロヘキサン、メチルシクロヘキサン、または様々な飽和炭化水素の混合物である。ベンゼン、トルエン、イソプロピルベンゼン、キシレンなどの芳香族炭化水素あるいはクロロベンゼン、ブロモベンゼン、またはオルトジクロロベンゼンなどのハロゲン化芳香族化合物を用いてもよい。その他の有用な溶剤としてはテトラヒドロフラン、ジオキサン等がある。
この一連の実験においては、10℃においてn-ブチル-リチウムの存在下でヘキサン溶液中のジビニルベンゼンの混合物に適当な第一アミンまたは第二アミンを添加することによって、3-(2-N-アルキルアミノエチル)スチレンと4-(2-N-アルキルアミノエチル)スチレンとの混合物が調製された。
この実験においては、3-(2-N-メチルアミノエチル)スチレンと4-(2-N-メチルアミノエチル)スチレンとの混合物単量体の上のアミン基がクロロトリメチルシランを用いて保護され、それによってそれが溶液重合の条件下で陰イオン開始剤を用いて重合されうるようにした。用いられた手順において、三つ口フラスコに1リットルのヘキサンと実施例2で合成された1モルの3,4-(2-アミノエチル)スチレン単量体が装填され、そして室温まで冷却された。次いで、2モルのトリメチルクロロシランが混合物に非常にゆっくりした速度で滴下して添加された。添加が完了した後、反応混合物は炭酸ナトリウムを用いて中和された。ヘキサン溶剤が除去され、そして残留物は真空蒸留された。得られた生成物は、C13NMRによって、3-(2-N,N-ジ-トリメチルシリルアミノエチル)スチレンと4-(2-N,N-ジ-トリメチルシリルアミノエチル)スチレンとの混合物であることが同定された。次いで、保護されたアミン基を有するこの単量体は、陰イオン重合において用いることができた。
ヘキサン中の19.50重量パーセントのスチレンと1,3-ブタジエンを含む2350gのシリカ/アルミナ/モレキュラーシーブ乾燥プレミックスを1ガロン(3.8リットル)の反応器の中に装填することによって、3,4-(2-アミノエチル)スチレン単量体で機能化されたスチレンブタジエンゴムを陰イオン溶液重合によって調製することができる。そのような重合においては、4.6グラムのニートな3-(2-N,N-ジ-トリメチルシリルアミノエチル)スチレンと4-(2-N,N-ジ-トリメチルシリルアミノエチル)スチレンとの混合物を、スチレン単量体とブタジエン単量体を収容した反応器の中に装填することができる。次いで、ヘキサン中のN,N,N’,N’-テトラメチルエチレンジアミン(TMEDA)の1M溶液2.9mlと1.6Mのn-ブチルリチウム(n-BuLi)2.3mlが、それぞれ反応器に添加された。そのような重合は70℃において90分間行なうことができる。全ての利用可能な単量体はその時間で消費され、次いで重合を停止させるためにエタノールが添加された。次いで、機能化したスチレンブタジエンゴムを反応器から取り出し、そして1phmの酸化防止剤を用いて安定化することができる。ヘキサン溶剤を蒸発させた後、得られた重合体を真空炉中で50℃において乾燥することができる。3-(2-N,N-ジ-トリメチルシリルアミノエチル)スチレンと4-(2-N,N-ジ-トリメチルシリルアミノエチル)スチレンとの混合物単量体の上の保護されたアミン基は、溶液から重合体を回収する間に脱保護され、3-(2-アミノエチル)スチレンと4-(2-アミノエチル)スチレンとの混合物が形成された。
この手順においては、実施例7で説明したのと同じ方法を繰り返すことができるが、ただし3-(2-N,N-ジ-トリメチルシリルアミノエチル)スチレンと4-(2-N,N-ジ-トリメチルシリルアミノエチル)スチレンとの混合物単量体は、反応器の中に装填される前にスチレン単量体およびブタジエン単量体とプレミックスされる。このような手順によって高いレベルの単量体の転化がもたらされるだろう。そして、製造された機能化したスチレンブタジエンゴムは、実施例7で説明したようにして回収することができる。
Claims (21)
- ゴム状組成物であって、(A)シリカ充填剤、(B)場合によってシリカカップリング剤(このシリカカップリング剤は5phr未満の量で存在する)、および(C)(1)少なくとも一つの共役ジオレフィン単量体と(2)次の構造式を有する機能化した単量体:
とから誘導された繰返し単位を含むゴム状重合体、
を含むゴム状組成物。 - 前記組成物はシリカカップリング剤を含んでいない、請求項1に記載のゴム状組成物。
- 前記ゴム状組成物は硬化される、請求項2に記載のゴム状組成物。
- 前記ゴム状組成物は硫黄を用いて硬化される、請求項3に記載のゴム状組成物。
- 前記シリカカップリング剤は1phr〜4phrの範囲内の量で存在する、請求項1に記載のゴム状組成物。
- 前記シリカカップリング剤は1phr〜2phrの範囲内の量で存在する、請求項1に記載のゴム状組成物。
- 機能化した単量体はゴム状重合体中に0.1重量パーセント〜5重量パーセントの範囲内の量で存在する、請求項1に記載のゴム状組成物。
- 外周のトレッドを伴う概ねドーナツ形をしたカーカス、間隔をおいた二つのビード、ビードからビードまで延びる少なくとも一つのプライ、および前記トレッドから放射状に延びていてトレッドを前記ビードに接続しているサイドウォールを含むタイヤであって、前記トレッドは接地するように適用され、このとき前記トレッドは(I)充填剤と(II)請求項1に記載のゴム状組成物を含む、前記タイヤ。
- 充填剤はシリカであり、そして前記トレッドはシリカカップリング剤を含んでいない、請求項8に記載のタイヤ。
- 前記トレッドは硬化される、請求項9に記載のタイヤ。
- 前記トレッドは硫黄を用いて硬化される、請求項10に記載のタイヤ。
- シリカカップリング剤は1phr〜4phrの範囲内の量で存在する、請求項8に記載のタイヤ。
- 前記シリカカップリング剤は1phr〜2phrの範囲内の量で存在する、請求項8に記載のタイヤ。
- トレッドはカーボンブラックをさらに含む、請求項8に記載のタイヤ。
- 機能化した単量体はゴム状重合体中に0.1重量パーセント〜5重量パーセントの範囲内の量で存在する、請求項8に記載のタイヤ。
- 乳化重合によってゴム状重合体を合成するための方法であって、(1)共役ジオレフィン単量体と(2)全単量体100重量部あたり0.1〜5重量部の次の構造式を有する機能化した単量体:
とを重合させることを含み、
前記重合は水性媒体中で行なわれ、そして前記重合は遊離基開始剤を用いて開始される、前記方法。 - 該機能化した単量体がパラ異性体とメタ異性体の混合物である、請求項1に記載のゴム状組成物。
- R 3 は水素原子であり、R 4 は水素原子である、請求項16に記載の重合体。
- R 3 は水素原子であり、R 4 は水素原子である、請求項17に記載の方法。
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US20070123631A1 (en) | 2007-05-31 |
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