JP2013082826A - 変性共役ジエン系重合体組成物 - Google Patents
変性共役ジエン系重合体組成物 Download PDFInfo
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- JP2013082826A JP2013082826A JP2011224296A JP2011224296A JP2013082826A JP 2013082826 A JP2013082826 A JP 2013082826A JP 2011224296 A JP2011224296 A JP 2011224296A JP 2011224296 A JP2011224296 A JP 2011224296A JP 2013082826 A JP2013082826 A JP 2013082826A
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- Prior art keywords
- conjugated diene
- modified conjugated
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- compound
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- 150000001993 dienes Chemical class 0.000 title claims abstract description 103
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- 229920001971 elastomer Polymers 0.000 claims abstract description 61
- 239000005060 rubber Substances 0.000 claims abstract description 56
- 239000003607 modifier Substances 0.000 claims abstract description 47
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- 230000009477 glass transition Effects 0.000 claims abstract description 33
- 229920001577 copolymer Polymers 0.000 claims abstract description 22
- 238000006116 polymerization reaction Methods 0.000 claims description 45
- 125000000524 functional group Chemical group 0.000 claims description 29
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- 238000012986 modification Methods 0.000 claims description 19
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- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000005370 alkoxysilyl group Chemical group 0.000 claims description 8
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 5
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
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- 230000037048 polymerization activity Effects 0.000 abstract 2
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- 125000003700 epoxy group Chemical group 0.000 description 6
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- 238000001179 sorption measurement Methods 0.000 description 6
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- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 5
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- 239000004606 Fillers/Extenders Substances 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
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- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
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- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- QIOYHIUHPGORLS-UHFFFAOYSA-N n,n-dimethyl-3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN(C)C QIOYHIUHPGORLS-UHFFFAOYSA-N 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical group OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 4
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- 239000011593 sulfur Substances 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- 235000014692 zinc oxide Nutrition 0.000 description 4
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- NGHSBFGVILHRKO-UHFFFAOYSA-N dimethoxymethyl-[3-(2-methoxy-2-methylazasilolidin-1-yl)propyl]silane Chemical compound CO[Si]1(N(CCC1)CCC[SiH2]C(OC)OC)C NGHSBFGVILHRKO-UHFFFAOYSA-N 0.000 description 1
- VNGOYPQMJFJDLV-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1 VNGOYPQMJFJDLV-UHFFFAOYSA-N 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
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- 230000007613 environmental effect Effects 0.000 description 1
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- 125000004185 ester group Chemical group 0.000 description 1
- ALSOCDGAZNNNME-UHFFFAOYSA-N ethene;hex-1-ene Chemical compound C=C.CCCCC=C ALSOCDGAZNNNME-UHFFFAOYSA-N 0.000 description 1
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- ZRIOTQSEPKLXSZ-UHFFFAOYSA-N ethyl N-[3-[diethoxy(propan-2-yloxy)silyl]propyl]-N-methylcarbamate Chemical compound CCOC(=O)N(CCC[Si](OC(C)C)(OCC)OCC)C ZRIOTQSEPKLXSZ-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
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- 238000011010 flushing procedure Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 150000008282 halocarbons Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 230000005660 hydrophilic surface Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
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- 239000012948 isocyanate Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229920003049 isoprene rubber Polymers 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- UIDWHMKSOZZDAV-UHFFFAOYSA-N lithium tin Chemical compound [Li].[Sn] UIDWHMKSOZZDAV-UHFFFAOYSA-N 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- AHNJTQYTRPXLLG-UHFFFAOYSA-N lithium;diethylazanide Chemical compound [Li+].CC[N-]CC AHNJTQYTRPXLLG-UHFFFAOYSA-N 0.000 description 1
- HOLCSXZMVPOUQR-UHFFFAOYSA-N lithium;dihexylazanide Chemical compound [Li+].CCCCCC[N-]CCCCCC HOLCSXZMVPOUQR-UHFFFAOYSA-N 0.000 description 1
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- YNXURHRFIMQACJ-UHFFFAOYSA-N lithium;methanidylbenzene Chemical compound [Li+].[CH2-]C1=CC=CC=C1 YNXURHRFIMQACJ-UHFFFAOYSA-N 0.000 description 1
- AXSMTZCJJBPZAA-UHFFFAOYSA-N lithium;morpholin-4-ide Chemical compound [Li]N1CCOCC1 AXSMTZCJJBPZAA-UHFFFAOYSA-N 0.000 description 1
- DWNRISLZVCBTRN-UHFFFAOYSA-N lithium;piperidin-1-ide Chemical compound [Li]N1CCCCC1 DWNRISLZVCBTRN-UHFFFAOYSA-N 0.000 description 1
- FJDQVJUXXNIHNB-UHFFFAOYSA-N lithium;pyrrolidin-1-ide Chemical compound [Li+].C1CC[N-]C1 FJDQVJUXXNIHNB-UHFFFAOYSA-N 0.000 description 1
- 238000010551 living anionic polymerization reaction Methods 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
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- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 150000002681 magnesium compounds Chemical class 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- VAJRBVISIJKTLZ-UHFFFAOYSA-N n,n,n',n'-tetramethylhexanediamide Chemical compound CN(C)C(=O)CCCCC(=O)N(C)C VAJRBVISIJKTLZ-UHFFFAOYSA-N 0.000 description 1
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 description 1
- ZLDHYRXZZNDOKU-UHFFFAOYSA-N n,n-diethyl-3-trimethoxysilylpropan-1-amine Chemical compound CCN(CC)CCC[Si](OC)(OC)OC ZLDHYRXZZNDOKU-UHFFFAOYSA-N 0.000 description 1
- XTOSZDRAGWRSBP-UHFFFAOYSA-N n,n-dimethyl-2-triethoxysilylethanamine Chemical compound CCO[Si](OCC)(OCC)CCN(C)C XTOSZDRAGWRSBP-UHFFFAOYSA-N 0.000 description 1
- RKOBOSOXEJGFTF-UHFFFAOYSA-N n,n-dimethyl-2-trimethoxysilylethanamine Chemical compound CO[Si](OC)(OC)CCN(C)C RKOBOSOXEJGFTF-UHFFFAOYSA-N 0.000 description 1
- AQIQPUUNTCVHBS-UHFFFAOYSA-N n,n-dimethyl-3-triethoxysilylpropan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCN(C)C AQIQPUUNTCVHBS-UHFFFAOYSA-N 0.000 description 1
- CNBZTHQYUOSCDJ-UHFFFAOYSA-N n-(3-triethoxysilylpropyl)butan-2-imine Chemical compound CCO[Si](OCC)(OCC)CCCN=C(C)CC CNBZTHQYUOSCDJ-UHFFFAOYSA-N 0.000 description 1
- PHYRCSSYBSJTMI-UHFFFAOYSA-N n-(3-triethoxysilylpropyl)ethanimine Chemical compound CCO[Si](OCC)(OCC)CCCN=CC PHYRCSSYBSJTMI-UHFFFAOYSA-N 0.000 description 1
- MPKNGASSKGJBSA-UHFFFAOYSA-N n-(3-triethoxysilylpropyl)propan-2-imine Chemical compound CCO[Si](OCC)(OCC)CCCN=C(C)C MPKNGASSKGJBSA-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- DLAUQJZKDAKQGO-UHFFFAOYSA-N n-butyl-n-(3-triethoxysilylpropyl)butan-1-amine Chemical compound CCCCN(CCCC)CCC[Si](OCC)(OCC)OCC DLAUQJZKDAKQGO-UHFFFAOYSA-N 0.000 description 1
- IJJSYKQZFFGIEE-UHFFFAOYSA-N naphthalene;potassium Chemical compound [K].C1=CC=CC2=CC=CC=C21 IJJSYKQZFFGIEE-UHFFFAOYSA-N 0.000 description 1
- URXNVXOMQQCBHS-UHFFFAOYSA-N naphthalene;sodium Chemical compound [Na].C1=CC=CC2=CC=CC=C21 URXNVXOMQQCBHS-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000005475 oxolanyl group Chemical group 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- UBOGEXSQACVGEC-UHFFFAOYSA-K phenyltin(3+);trichloride Chemical compound Cl[Sn](Cl)(Cl)C1=CC=CC=C1 UBOGEXSQACVGEC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 125000002270 phosphoric acid ester group Chemical group 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000768 polyamine Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000346 polystyrene-polyisoprene block-polystyrene Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 150000003112 potassium compounds Chemical class 0.000 description 1
- ZRLVQFQTCMUIRM-UHFFFAOYSA-N potassium;2-methylbutan-2-olate Chemical compound [K+].CCC(C)(C)[O-] ZRLVQFQTCMUIRM-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- ZMYXZXUHYAGGKG-UHFFFAOYSA-N propoxysilane Chemical compound CCCO[SiH3] ZMYXZXUHYAGGKG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003298 rubidium compounds Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- AIFMYMZGQVTROK-UHFFFAOYSA-N silicon tetrabromide Chemical compound Br[Si](Br)(Br)Br AIFMYMZGQVTROK-UHFFFAOYSA-N 0.000 description 1
- 239000005049 silicon tetrachloride Substances 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
- 150000003388 sodium compounds Chemical class 0.000 description 1
- PDEFQWNXOUGDJR-UHFFFAOYSA-M sodium;2,2-dichloropropanoate Chemical compound [Na+].CC(Cl)(Cl)C([O-])=O PDEFQWNXOUGDJR-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
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- 235000012424 soybean oil Nutrition 0.000 description 1
- 150000003438 strontium compounds Chemical class 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram 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
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- KBSUPJLTDMARAI-UHFFFAOYSA-N tribromo(methyl)silane Chemical compound C[Si](Br)(Br)Br KBSUPJLTDMARAI-UHFFFAOYSA-N 0.000 description 1
- QCYLWGCOMDCVLQ-UHFFFAOYSA-N tribromomethoxysilane Chemical compound [SiH3]OC(Br)(Br)Br QCYLWGCOMDCVLQ-UHFFFAOYSA-N 0.000 description 1
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 description 1
- MEBRQLCKPRKBOH-UHFFFAOYSA-K trichloro(ethyl)stannane Chemical compound CC[Sn](Cl)(Cl)Cl MEBRQLCKPRKBOH-UHFFFAOYSA-K 0.000 description 1
- LFXJGGDONSCPOF-UHFFFAOYSA-N trichloro(hexyl)silane Chemical compound CCCCCC[Si](Cl)(Cl)Cl LFXJGGDONSCPOF-UHFFFAOYSA-N 0.000 description 1
- YFRLQYJXUZRYDN-UHFFFAOYSA-K trichloro(methyl)stannane Chemical compound C[Sn](Cl)(Cl)Cl YFRLQYJXUZRYDN-UHFFFAOYSA-K 0.000 description 1
- OEBWMIHWFIEUFN-UHFFFAOYSA-N trichloromethoxysilane Chemical compound [SiH3]OC(Cl)(Cl)Cl OEBWMIHWFIEUFN-UHFFFAOYSA-N 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- LENYMJLFWIMHEP-UHFFFAOYSA-N triethoxy(3-pyrrolidin-1-ylpropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN1CCCC1 LENYMJLFWIMHEP-UHFFFAOYSA-N 0.000 description 1
- ASAOXGWSIOQTDI-UHFFFAOYSA-N triethoxy-[2-(2-triethoxysilylethyltetrasulfanyl)ethyl]silane Chemical compound CCO[Si](OCC)(OCC)CCSSSSCC[Si](OCC)(OCC)OCC ASAOXGWSIOQTDI-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- HPDURSIFGBKQQA-UHFFFAOYSA-N triethoxy-[3-(2-ethoxy-2-ethylazasilolidin-1-yl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCN1CCC[Si]1(CC)OCC HPDURSIFGBKQQA-UHFFFAOYSA-N 0.000 description 1
- LUHSQMWOOCBXIL-UHFFFAOYSA-N triethoxy-[3-(3-methyl-1,3-diazinan-1-yl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCN1CCCN(C)C1 LUHSQMWOOCBXIL-UHFFFAOYSA-N 0.000 description 1
- FBBATURSCRIBHN-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSCCC[Si](OCC)(OCC)OCC FBBATURSCRIBHN-UHFFFAOYSA-N 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- SPABUJYCCHPCCW-UHFFFAOYSA-N triethoxy-[3-(3-trimethylsilyl-1,3-diazinan-1-yl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCN1CCCN([Si](C)(C)C)C1 SPABUJYCCHPCCW-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- AOKNSKHTJMRBHF-UHFFFAOYSA-N triethoxy-[3-[4-(3-triethoxysilylpropyl)piperazin-1-yl]propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCN1CCN(CCC[Si](OCC)(OCC)OCC)CC1 AOKNSKHTJMRBHF-UHFFFAOYSA-N 0.000 description 1
- NGLLPRYTJGRGEU-UHFFFAOYSA-N trimethoxy(3-pyrrolidin-1-ylpropyl)silane Chemical compound CO[Si](OC)(OC)CCCN1CCCC1 NGLLPRYTJGRGEU-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- RKOJULISMXLJRL-UHFFFAOYSA-N trimethoxy-[3-(3-methylimidazolidin-1-yl)propyl]silane Chemical compound CO[Si](OC)(OC)CCCN1CCN(C)C1 RKOJULISMXLJRL-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
- XNWCJGVZGOCGBT-UHFFFAOYSA-N trimethoxy-[3-[4-(3-trimethoxysilylpropyl)piperazin-1-yl]propyl]silane Chemical compound CO[Si](OC)(OC)CCCN1CCN(CCC[Si](OC)(OC)OC)CC1 XNWCJGVZGOCGBT-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Tires In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
〔1〕
重合活性末端を持つ共役ジエン系重合体の該重合活性末端に、下記式(1)で表される変性剤を反応させて得られ、ガラス転移温度が−120〜−60℃である(A)変性共役ジエン系重合体と、
ガラス転移温度が−50〜−5℃である(B)変性共役ジエン−芳香族ビニル系共重合体と、を含むゴム成分、及び
(C)シリカ
を含有する、変性共役ジエン系重合体組成物。
〔2〕
前記(B)成分は、窒素原子及び/又は酸素原子を有する官能基を含有し、かつ、アルコキシシリル基を含有する変性剤で共重合体末端が変性されている、〔1〕に記載の変性共役ジエン系重合体組成物。
〔3〕
前記ゴム成分100質量部中の前記(A)成分と前記(B)成分の合計含有量が、50〜100質量部であり、
前記(B)成分に対する前記(A)成分の質量比((A)/(B))が、5/95〜70/30である、〔1〕又は〔2〕に記載の変性共役ジエン系重合体組成物。
〔4〕
前記ゴム成分100質量部に対する、前記(C)シリカの含有量が、20〜150質量部である、〔1〕〜〔3〕のいずれか一項に記載の変性共役ジエン系重合体組成物。
重合活性末端を持つ共役ジエン系共重合体の該重合活性末端に、下記式(1)で表される変性剤を反応させて得られ、ガラス転移温度が−120〜−60℃である(A)変性共役ジエン系重合体と、
ガラス転移温度が−50〜−5℃である(B)変性共役ジエン−芳香族ビニル系共重合体と、を含むゴム成分、及び、
(C)シリカ、を含有する。
その他の軟化剤としては、公知の軟化剤を用いることができる。
その他の充填剤としては、例えば、炭酸カルシウム、炭酸マグネシウム、硫酸アルミニウム、硫酸バリウム等が挙げられる。
耐熱安定剤、帯電防止剤、耐候安定剤、老化防止剤、着色剤、滑剤としては、それぞれ公知の材料を用いることができる。
試料100mgをクロロホルムで100mLにメスアップし、クロロホルムに溶解させて測定サンプルとした。測定サンプルについて、スチレンのフェニル基によるUV254nmの吸収により結合スチレン量(質量%)を測定した(島津製作所社製、紫外可視分光光度計「UV−2450」)。
試料50mgを10mLの二硫化炭素に溶解して測定サンプルとした。溶液セルを用いて、赤外線スペクトルを600〜1000cm-1の範囲で測定して所定の波数における吸光度によりハンプトンの方法の計算式に従いブタジエン部分のミクロ構造を求めた(日本分光社製、フーリエ変換赤外分光光度計「FT−IR230」)。
ムーニー粘度計(上島製作所社製、「VR1132」)を用い、JIS K6300に準拠しL形ロータを用いて、ムーニー粘度を測定した。測定温度は100℃で、まず、試料を1分間予熱した後、2rpmでローターを回転させ、4分後のトルクを測定してムーニー粘度(ML1+4)とした。
ISO 22768:2006に準拠して、マックサイエンス社製、示差走査熱量計「DSC3200S」を用い、ヘリウム50mL/分の流通下、−100℃、あるいはガラス転移温度よりも30℃以上低い温度のいずれかの、より低い温度から、20℃/分で昇温しながらDSC曲線を記録し、DSC微分曲線のピークトップ(Inflection point)をガラス転移温度とした。
ポリスチレン系ゲルを充填剤としたカラムを3本連結したGPC測定装置を使用して、クロマトグラムを測定し、標準ポリスチレンを使用した検量線に基づいて重量平均分子量(Mw)と数平均分子量(Mn)を求めた。溶離液はテトラヒドロフラン(THF)を使用した。カラムは、ガードカラム:東ソー社製 TSKguardcolumn HHR−H、カラム:東ソー社製 TSKgel G6000HHR、TSKgel G5000HHR、TSKgel G4000HHRを使用した。オーブン温度40℃、THF流量1.0mL/分の条件で、RI検出器(東ソー社製、「HLC8020」)を用いた。測定用の試料10mgを20mLのTHFに溶解して測定溶液とし、測定溶液200μLをGPC測定装置に注入して測定した。
シリカ系ゲルを充填剤としたGPCカラムに変性した成分が吸着する特性を応用することにより測定した。試料及び低分子量内部標準ポリスチレンを含む試料溶液を、ポリスチレン系ゲルカラムで測定したクロマトグラムと、シリカ系カラムで測定したクロマトグラムの差分よりシリカカラムへの吸着量を測定し変性率を求めた。
・試料溶液の調製:
試料10mg及び標準ポリスチレン5mgを20mLのTHFに溶解させて、試料溶液とした。
・ポリスチレン系カラムを用いたGPC測定条件:
THFを溶離液として用い、試料溶液200μLを装置に注入して測定した。カラムは、ガードカラム:東ソー社製 TSKguardcolumn HHR−H、カラム:東ソー TSKgel G6000HHR、TSKgel G5000HHR、TSKgel G4000HHRを使用した。カラムオーブン温度40℃、THF流量1.0mL/分の条件で、RI検出器(東ソー社製 「HLC8020」)を用いて測定し、クロマトグラムを得た。
・シリカ系カラムを用いたGPC測定条件:
THFを溶離液として用い、試料溶液200μLを装置に注入して測定した。カラムは、ガードカラム:DIOL 4.6×12.5mm 5micron、カラム:Zorbax PSM−1000S、PSM−300S、PSM−60Sを使用した。カラムオーブン温度40℃、THF流量0.5mL/分で、東ソー社製 「CCP8020シリーズ」 ビルドアップ型GPCシステム:AS−8020、SD−8022、CCPS、CO−8020、RI−8021で、RI検出器を用いて測定し、クロマトグラムを得た。
・変性率の計算方法:
ポリスチレン系カラムを用いたクロマトグラムのピーク面積の全体を100として、試料のピーク面積をP1、標準ポリスチレンのピーク面積をP2、シリカ系カラムを用いたクロマトグラムのピーク面積の全体を100として、試料のピーク面積をP3、標準ポリスチレンのピーク面積をP4として、下記式より変性率(%)を求めた。
変性率(%)=[1−(P2×P3)/(P1×P4)]×100
(ただし、P1+P2=P3+P4=100)
内容積10Lで、撹拌機及びジャケットを具備する温度制御が可能なオートクレーブを反応器として使用し、予め不純物を除去した、1,3−ブタジエン1050g、シクロヘキサン4800g、極性物質として2,2−ビス(2−オキソラニル)プロパン0.09gを反応器へ入れ、反応器内温を47℃に保持した。重合開始剤として、n−ブチルリチウム16.15mmolを含むシクロヘキサン溶液を反応器に供給した。重合反応開始後、重合による発熱で反応器内の温度は上昇を始め、最終的な反応器内の温度は82℃に達した。反応温度のピーク到達2分後、反応器に変性剤として2,2−ジメトキシ−1−(3−トリメトキシシリルプロピル)−1−アザ−2−シラシクロペンタンを3.23mmol添加し、80℃で5分間変性反応を実施して、変性重合体溶液を得た。
この変性重合体溶液に、酸化防止剤(2,6−ジ−tert−ブチル−4−ヒドロキシトルエン;BHT)2.1gを添加した後、スチームストリッピングにより溶媒を除去し、乾燥機により乾燥処理を施して、変性共役ジエン系重合体(試料a)を得た。
試料aを分析した結果、100℃でのムーニー粘度は65、ブタジエン結合単位中のビニル結合量(1,2−結合量)は18モル%、ガラス転移温度は−90℃、変性率は88%であった。試料aの分析結果を表1に示した。
モノマーとして1,3−ブタジエンの添加量を945gとし、スチレンを105g用いて重合を行い、変性剤として2,2−ジメトキシ−1−(3−トリメトキシシリルプロピル)−1−アザ−2−シラシクロペンタンに替えて、2,2−ジメトキシ−1−(4−トリメトキシシリルブチル)−1−アザ−2−シラシクロヘキサンを使用した以外は製造例1と同様にして、変性共役ジエン系重合体(試料b)を得た。
試料bを分析した結果、100℃でのムーニー粘度は60、結合スチレン量は10質量%、ブタジエン結合単位中のビニル結合量(1,2−結合量)は17モル%、ガラス転移温度は−75℃、変性率は86%であった。試料bの分析結果を表1に示した。
内容積10Lで、内部の高さと直径の比(L/D)が4であり、底部に入り口、頂部に出口を有し、撹拌機及び温度調整用のジャケットを有するオートクレーブを2基直列に連結し、1基目を重合反応器として、2基目を変性反応器とした。
予め、水分等の不純物を除去した、1,3−ブタジエンを32.5g/分、n−ヘキサンを138.6g/分、及び重合開始剤としてn−ブチルリチウムを0.964mmol/分の速度で、1基目反応器の底部へ供給し、反応器頂部での反応器内の重合体溶液の温度が100℃となるように重合反応を継続させた。
1基目の反応器頂部より連続的に流出する重合体溶液を2基目の反応器底部に供給し、更に、変性剤として2,2−ジメトキシ−1−(3−トリメトキシシリルプロピル)−1−アザ−2−シラシクロペンタンを0.24mmol/分の速度で2基目反応器の底部から添加し、2基目の反応器内部の重合体溶液の温度を90℃に保ちながら変性反応を実施した。2基目反応器の頂部から流出した変性重合体溶液に酸化防止剤(BHT)のn−ヘキサン溶液を、変性重合体100gあたり酸化防止剤0.2gとなるように連続的に添加し、変性反応を終了させ、その後溶媒を除去し、変性共役ジエン系重合体(試料c)を得た。
試料cを分析した結果、100℃のムーニー粘度は61であった。ブタジエン結合単位中のビニル結合量(1,2−結合量)は13モル%、ガラス転移温度は−94℃、変性率は82%であった。試料cの分析結果を表1に示す。
n−ブチルリチウムの添加量を6.52mmol、2,2−ビス(2−オキソラニル)プロパンの添加量を0.03gとし、変性剤として2,2−ジメトキシ−1−(3−トリメトキシシリルプロピル)−1−アザ−2−シラシクロペンタンに替えて、[3−(ジメチルアミノ)プロピル]トリメトキシシランを4.35mmol添加した以外は製造例1と同様にして、変性共役ジエン系重合体(試料d)を得た。
試料dを分析した結果、100℃でのムーニー粘度は61、ブタジエン結合単位中のビニル結合量は18モル%、ガラス転移温度は−90℃、変性率は89%であった。試料dの分析結果を表2に示した。
市販の非変性高シスポリブタジエンゴム(宇部興産社製、「UBEPOL BR150」)(試料e)を用意した。試料eの分析結果を表2に示した。
内容積10Lで、撹拌機及びジャケットを具備する温度制御が可能なオートクレーブを反応器として使用し、予め不純物を除去した、1,3−ブタジエン777g、スチレン273g、シクロヘキサン4800g、極性物質として2,2−ビス(2−オキソラニル)プロパン0.63gを反応器へ入れ、反応器内温を42℃に保持した。重合開始剤として、n−ブチルリチウム6.52mmolを含むシクロヘキサン溶液を反応器に供給した。重合反応開始後、重合による発熱で反応器内の温度は上昇を始め、最終的な反応器内の温度は77℃に達した。反応温度のピーク到達2分後、反応器に変性剤として1−[3−(トリエトキシシリル)プロピル]−4−メチルピペラジンを3.91mmol添加し、75℃で5分間変性反応を実施して、変性共重合体溶液を得た。
この変性共重合体溶液に、酸化防止剤(2,6−ジ−tert−ブチル−4−ヒドロキシトルエン;BHT)2.1gを添加した後、スチームストリッピングにより溶媒を除去し、乾燥機により乾燥処理を施して、変性共役ジエン−芳香族ビニル系共重合体(試料f)を得た。
試料fを分析した結果、100℃でのムーニー粘度は59、結合スチレン量は26質量%、ブタジエン結合単位中のビニル結合量(1,2−結合量)は56モル%、ガラス転移温度は−25℃、変性率は89%であった。試料fの分析結果を表3に示した。
1,3-ブタジエンの添加量を756g、スチレンの添加量を294g、2,2−ビス(2−オキソラニル)プロパンの添加量を1.85g、n−ブチルリチウムの添加量を15.1mmolとし、変性剤として1−[3−(トリエトキシシリル)プロピル]−4−メチルピペラジンに替えて2,2−ジメトキシ−1−(3−トリメトキシシリルプロピル)−1−アザ−2−シラシクロペンタンを2.72mmol使用した以外は製造例5と同様にして、変性共役ジエン−芳香族ビニル系共重合体(試料g)を得た。
試料gを分析した結果、100℃でのムーニー粘度は62、結合スチレン量は28質量%、ブタジエン結合単位中のビニル結合量(1,2−結合量)は60モル%、ガラス転移温度は−19℃、変性率は88%であった。試料gの分析結果を表3に示した。
1,3-ブタジエンの添加量を892g、スチレンの添加量を158g、2,2−ビス(2−オキソラニル)プロパンの添加量を0.52g、とし、変性剤として1−[3−(トリエトキシシリル)プロピル]−4−メチルピペラジンに替えて[3−(ジメチルアミノ)プロピル]トリメトキシシランを3.91mmol使用した以外は製造例5と同様にして、変性共役ジエン−芳香族ビニル系共重合体(試料h)を得た。
試料hを分析した結果、100℃でのムーニー粘度は57、結合スチレン量は15質量%、ブタジエン結合単位中のビニル結合量(1,2−結合量)は52モル%、ガラス転移温度は−42℃、変性率は88%であった。試料hの分析結果を表3に示した。
MSPASP:2,2−ジメトキシ−1−(3−トリメトキシシリルプロピル)−1−アザ−2−シラシクロペンタン
MSBASH:2,2−ジメトキシ−1−(4−トリメトキシシリルブチル)−1−アザ−2−シラシクロヘキサン
DMATMS:[3−(ジメチルアミノ)プロピル]トリメトキシシラン
TESMP:1−[3−(トリエトキシシリル)プロピル]−4−メチルピペラジン
*2
宇部興産社製の非変性高シスポリブタジエンゴム 「UBEPOL BR150」
表1〜3に示す試料(試料a〜h)を原料ゴムとして、以下に示す配合に従い、それぞれの原料ゴムを含有するゴム組成物を得た。
変性共役ジエン系重合体(A成分)、変性共役ジエンジエン−芳香族ビニル系共重合体(B成分)の合計:100.0質量部
シリカ(エボニック デグサ社製、Ultrasil 7000GR、窒素吸着比表面積:175m2/g):75.0質量部
カーボンブラック(東海カーボン社製、シーストKH(N339)):5.0質量部
シランカップリング剤(エボニック デグサ社製、Si75):6.0質量部
S−RAEオイル(JX日鉱日石エネルギー社製、JOMOプロセスNC140):30.0質量部
亜鉛華:2.5質量部
ステアリン酸:2.0質量部
老化防止剤(N−イソプロピル−N’−フェニル−p−フェニレンジアミン):2.0質量部
硫黄:1.7質量部
加硫促進剤(N−シクロヘキシル−2−ベンゾチアジルスルフィンアミド):1.7質量部
加硫促進剤(ジフェニルグアニジン):2.0質量部
合計:227.9質量部
上記した材料を下記の方法により混練してゴム組成物を得た。
温度制御装置を具備する密閉混練機(内容量0.3L)を使用し、第一段の混練として、充填率65%、ローター回転数50/57rpmの条件で、原料ゴム(試料a〜h)、充填剤(シリカ、カーボンブラック)、有機シランカップリング剤、プロセスオイル、亜鉛華、ステアリン酸を混練した。このとき、密閉混合機の温度を制御し、排出温度は155〜160℃でゴム組成物(配合物)を得た。
(1)配合物ムーニー粘度
ムーニー粘度計を使用し、JIS K6300−1に準拠してL形ロータを用い、130℃、1分間の予熱を行った後に、ローターを毎分2回転で4分間回転させた後の粘度を測定した。値が小さいほど加工性に優れることを示す。
JIS K6251の引張試験法に準拠して測定し、比較例1の結果を100として指数化した。
レオメトリックス・サイエンティフィック社製の粘弾性試験機「ARES」を使用し、ねじりモードで粘弾性パラメータを測定した。各々の測定値は比較例1を100として指数化した。0℃において周波数10Hz、ひずみ1%で測定したtanδをウェットスキッド抵抗性の指標とした。値が大きいほどウェットスキッド抵抗性が良好であることを示す。また、50℃において周波数10Hz、ひずみ3%で測定したtanδを低発熱性の指標とした。値が小さいほど低発熱で、省燃費性能が良好であることを示す。
Claims (4)
- 前記(B)成分は、窒素原子及び/又は酸素原子を有する官能基を含有し、かつ、アルコキシシリル基を含有する変性剤で共重合体末端が変性されている、請求項1に記載の変性共役ジエン系重合体組成物。
- 前記ゴム成分100質量部中の前記(A)成分と前記(B)成分の合計含有量が、50〜100質量部であり、
前記(B)成分に対する前記(A)成分の質量比((A)/(B))が、5/95〜70/30である、請求項1又は2に記載の変性共役ジエン系重合体組成物。 - 前記ゴム成分100質量部に対する、前記(C)シリカの含有量が、20〜150質量部である、請求項1〜3のいずれか一項に記載の変性共役ジエン系重合体組成物。
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JP2016017097A (ja) * | 2014-07-04 | 2016-02-01 | 旭化成ケミカルズ株式会社 | 変性共役ジエン系重合体組成物 |
EP3059260A4 (en) * | 2013-10-17 | 2016-08-24 | Lg Chemical Ltd | CONJUGATED DYE POLYMER FUNCTIONALIZED IN CHAIN END AND PROCESS FOR PRODUCING THE SAME |
WO2016133202A1 (ja) * | 2015-02-19 | 2016-08-25 | 旭化成株式会社 | 変性共役ジエン系重合体及びその製造方法、並びに変性共役ジエン系重合体組成物 |
JP2016196547A (ja) * | 2015-04-03 | 2016-11-24 | 横浜ゴム株式会社 | タイヤ用ゴム組成物 |
JP2017002168A (ja) * | 2015-06-09 | 2017-01-05 | 株式会社ブリヂストン | ポリブタジエンの製造方法 |
EP3103816A4 (en) * | 2014-11-27 | 2017-01-18 | LG Chem, Ltd. | End-functional conjugated diene-based polymer and method of preparing same |
CN113372630A (zh) * | 2020-03-10 | 2021-09-10 | 旭化成株式会社 | 共轭二烯系聚合物组合物以及轮胎 |
KR20210125427A (ko) * | 2020-04-08 | 2021-10-18 | 아사히 가세이 가부시키가이샤 | 공액 디엔계 중합체 및 그의 제조 방법, 그리고 고무 조성물 |
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EP3059260A4 (en) * | 2013-10-17 | 2016-08-24 | Lg Chemical Ltd | CONJUGATED DYE POLYMER FUNCTIONALIZED IN CHAIN END AND PROCESS FOR PRODUCING THE SAME |
US9644045B2 (en) | 2013-10-17 | 2017-05-09 | Lg Chem, Ltd. | End-functionalized conjugated diene-based polymer and process for producing same |
JP2016017097A (ja) * | 2014-07-04 | 2016-02-01 | 旭化成ケミカルズ株式会社 | 変性共役ジエン系重合体組成物 |
EP3103816A4 (en) * | 2014-11-27 | 2017-01-18 | LG Chem, Ltd. | End-functional conjugated diene-based polymer and method of preparing same |
US10023661B2 (en) | 2014-11-27 | 2018-07-17 | Lg Chem, Ltd. | End-functional conjugated diene-based polymer and method of preparing same |
US10766972B2 (en) | 2015-02-19 | 2020-09-08 | Asahi Kasei Kabushiki Kaisha | Modified conjugated diene-based polymer and method for producing the same, and modified conjugated diene-based polymer composition |
JPWO2016133202A1 (ja) * | 2015-02-19 | 2017-11-02 | 旭化成株式会社 | 変性共役ジエン系重合体及びその製造方法、並びに変性共役ジエン系重合体組成物 |
WO2016133202A1 (ja) * | 2015-02-19 | 2016-08-25 | 旭化成株式会社 | 変性共役ジエン系重合体及びその製造方法、並びに変性共役ジエン系重合体組成物 |
JP2016196547A (ja) * | 2015-04-03 | 2016-11-24 | 横浜ゴム株式会社 | タイヤ用ゴム組成物 |
JP2017002168A (ja) * | 2015-06-09 | 2017-01-05 | 株式会社ブリヂストン | ポリブタジエンの製造方法 |
CN113372630A (zh) * | 2020-03-10 | 2021-09-10 | 旭化成株式会社 | 共轭二烯系聚合物组合物以及轮胎 |
KR20210125427A (ko) * | 2020-04-08 | 2021-10-18 | 아사히 가세이 가부시키가이샤 | 공액 디엔계 중합체 및 그의 제조 방법, 그리고 고무 조성물 |
KR102527631B1 (ko) * | 2020-04-08 | 2023-05-03 | 아사히 가세이 가부시키가이샤 | 공액 디엔계 중합체 및 그의 제조 방법, 그리고 고무 조성물 |
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