WO2012011571A1 - ゴム組成物及び空気入りタイヤ - Google Patents
ゴム組成物及び空気入りタイヤ Download PDFInfo
- Publication number
- WO2012011571A1 WO2012011571A1 PCT/JP2011/066705 JP2011066705W WO2012011571A1 WO 2012011571 A1 WO2012011571 A1 WO 2012011571A1 JP 2011066705 W JP2011066705 W JP 2011066705W WO 2012011571 A1 WO2012011571 A1 WO 2012011571A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- formula
- mass
- rubber composition
- polymer
- Prior art date
Links
- 229920001971 elastomer Polymers 0.000 title claims abstract description 65
- 239000005060 rubber Substances 0.000 title claims abstract description 65
- 239000000203 mixture Substances 0.000 title claims abstract description 50
- 229920000642 polymer Polymers 0.000 claims abstract description 142
- 150000001993 dienes Chemical class 0.000 claims abstract description 54
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 53
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 26
- 150000003377 silicon compounds Chemical class 0.000 claims abstract description 20
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 84
- 125000004432 carbon atom Chemical group C* 0.000 claims description 62
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 229920002554 vinyl polymer Polymers 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 244000043261 Hevea brasiliensis Species 0.000 claims description 13
- 239000005062 Polybutadiene Substances 0.000 claims description 13
- 229920003052 natural elastomer Polymers 0.000 claims description 13
- 229920001194 natural rubber Polymers 0.000 claims description 13
- 238000001179 sorption measurement Methods 0.000 claims description 8
- 229920002857 polybutadiene Polymers 0.000 claims description 6
- 239000000470 constituent Substances 0.000 claims description 5
- 239000000446 fuel Substances 0.000 abstract description 35
- -1 dimethylaminoethyl group Chemical group 0.000 description 100
- 238000006116 polymerization reaction Methods 0.000 description 81
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 66
- 239000000243 solution Substances 0.000 description 64
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 62
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 62
- 125000000217 alkyl group Chemical group 0.000 description 52
- 125000003277 amino group Chemical group 0.000 description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 24
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 22
- 239000000178 monomer Substances 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 238000003756 stirring Methods 0.000 description 20
- 238000004519 manufacturing process Methods 0.000 description 19
- 125000001424 substituent group Chemical group 0.000 description 19
- 238000004073 vulcanization Methods 0.000 description 19
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
- 125000004663 dialkyl amino group Chemical group 0.000 description 17
- 238000000034 method Methods 0.000 description 17
- 229910052783 alkali metal Inorganic materials 0.000 description 16
- 150000001340 alkali metals Chemical class 0.000 description 16
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 16
- 125000003545 alkoxy group Chemical group 0.000 description 15
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 14
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 14
- 239000006229 carbon black Substances 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 13
- MQWJCFBYOCOAQO-UHFFFAOYSA-N N-[diethylamino(prop-1-enyl)silyl]-N-ethylethanamine Chemical group C(C)N(CC)[SiH](C=CC)N(CC)CC MQWJCFBYOCOAQO-UHFFFAOYSA-N 0.000 description 12
- 125000002015 acyclic group Chemical group 0.000 description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- 125000002947 alkylene group Chemical group 0.000 description 11
- 150000002430 hydrocarbons Chemical group 0.000 description 11
- 125000004430 oxygen atom Chemical group O* 0.000 description 11
- 239000006087 Silane Coupling Agent Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 10
- 229930195733 hydrocarbon Natural products 0.000 description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 125000004665 trialkylsilyl group Chemical group 0.000 description 10
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 9
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 9
- 230000005484 gravity Effects 0.000 description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
- 239000004215 Carbon black (E152) Substances 0.000 description 8
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 8
- IORUEKDKNHHQAL-UHFFFAOYSA-N [2-tert-butyl-6-[(3-tert-butyl-2-hydroxy-5-methylphenyl)methyl]-4-methylphenyl] prop-2-enoate Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)OC(=O)C=C)=C1O IORUEKDKNHHQAL-UHFFFAOYSA-N 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 238000013329 compounding Methods 0.000 description 8
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
- 229910052710 silicon Inorganic materials 0.000 description 8
- 229910001220 stainless steel Inorganic materials 0.000 description 8
- 239000010935 stainless steel Substances 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 125000002897 diene group Chemical group 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 238000007334 copolymerization reaction Methods 0.000 description 6
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 6
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 6
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 238000005299 abrasion Methods 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 5
- 238000004898 kneading Methods 0.000 description 5
- 125000006606 n-butoxy group Chemical group 0.000 description 5
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 5
- 125000005920 sec-butoxy group Chemical group 0.000 description 5
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 4
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 238000005096 rolling process Methods 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 239000004636 vulcanized rubber Substances 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- KLTSETMIIMRWGO-UHFFFAOYSA-N N-[(dipropylamino)-prop-1-enylsilyl]-N-propylpropan-1-amine Chemical group C(CC)N(CCC)[SiH](C=CC)N(CCC)CCC KLTSETMIIMRWGO-UHFFFAOYSA-N 0.000 description 3
- FQPBBMOBTFSDHU-UHFFFAOYSA-N N-butyl-N-[(dibutylamino)-prop-1-enylsilyl]butan-1-amine Chemical group CC=C[SiH](N(CCCC)CCCC)N(CCCC)CCCC FQPBBMOBTFSDHU-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001339 alkali metal compounds 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
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 3
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- 230000003014 reinforcing effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229940014800 succinic anhydride Drugs 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 2
- WVAFEFUPWRPQSY-UHFFFAOYSA-N 1,2,3-tris(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1C=C WVAFEFUPWRPQSY-UHFFFAOYSA-N 0.000 description 2
- QLLUAUADIMPKIH-UHFFFAOYSA-N 1,2-bis(ethenyl)naphthalene Chemical compound C1=CC=CC2=C(C=C)C(C=C)=CC=C21 QLLUAUADIMPKIH-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 2
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- 0 C*(*NN(*)C(*)*)C(C)=O Chemical compound C*(*NN(*)C(*)*)C(C)=O 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 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
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 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 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-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
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000003712 anti-aging effect Effects 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 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 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002642 lithium compounds Chemical class 0.000 description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- FIRXZHKWFHIBOF-UHFFFAOYSA-N n-(dimethylamino-ethenyl-methylsilyl)-n-methylmethanamine Chemical compound CN(C)[Si](C)(C=C)N(C)C FIRXZHKWFHIBOF-UHFFFAOYSA-N 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- PLGLPMXIBOWGOL-UHFFFAOYSA-N n-methyl-n-(3-triethoxysilylpropyl)propanamide Chemical compound CCO[Si](OCC)(OCC)CCCN(C)C(=O)CC PLGLPMXIBOWGOL-UHFFFAOYSA-N 0.000 description 2
- OCTBQOFPWLCNLD-UHFFFAOYSA-N n-methyl-n-(3-trimethoxysilylpropyl)propanamide Chemical compound CCC(=O)N(C)CCC[Si](OC)(OC)OC OCTBQOFPWLCNLD-UHFFFAOYSA-N 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 2
- 229940080818 propionamide Drugs 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 150000003388 sodium compounds Chemical class 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 229960002447 thiram Drugs 0.000 description 2
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 2
- JPMBLOQPQSYOMC-UHFFFAOYSA-N trimethoxy(3-methoxypropyl)silane Chemical compound COCCC[Si](OC)(OC)OC JPMBLOQPQSYOMC-UHFFFAOYSA-N 0.000 description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
- BYXIHUNXHHGLJN-UHFFFAOYSA-N trimethoxy-[3-(oxolan-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CCCO1 BYXIHUNXHHGLJN-UHFFFAOYSA-N 0.000 description 2
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- MYOKPSNMMVMHBI-UHFFFAOYSA-N 1,1-diethoxyethane;potassium Chemical compound [K].CCOC(C)OCC MYOKPSNMMVMHBI-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 description 1
- DLQFLDJHAGXWMQ-UHFFFAOYSA-N 1-[bis(trimethylsilyl)amino]silyl-2-methylprop-1-ene Chemical compound C[Si](C)(C)N([Si](C)(C)C)[SiH2]C=C(C)C DLQFLDJHAGXWMQ-UHFFFAOYSA-N 0.000 description 1
- DUFYAFHRXCROCT-UHFFFAOYSA-N 1-[bis(trimethylsilyl)amino]silylprop-1-ene Chemical compound C[Si](C)(C)N([Si](C)(C)C)[SiH2]C=CC DUFYAFHRXCROCT-UHFFFAOYSA-N 0.000 description 1
- JNAJROBGNKKASE-UHFFFAOYSA-N 1-[bis[tert-butyl(dimethyl)silyl]amino]silyl-2-methylprop-1-ene Chemical compound C(C)(C)(C)[Si](C)(C)N([Si](C(C)(C)C)(C)C)[SiH2]C=C(C)C JNAJROBGNKKASE-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- KPIIFJXDGKNFNH-UHFFFAOYSA-N 2-[[[tert-butyl(dimethyl)silyl]-[ethenyl(ethyl)silyl]amino]-dimethylsilyl]-2-methylpropane Chemical compound C(C)(C)(C)[Si](C)(C)N([Si](C(C)(C)C)(C)C)[SiH](C=C)CC KPIIFJXDGKNFNH-UHFFFAOYSA-N 0.000 description 1
- GXOWWGBQEWDONC-UHFFFAOYSA-N 2-[[[tert-butyl(dimethyl)silyl]-prop-1-enylsilylamino]-dimethylsilyl]-2-methylpropane Chemical compound [Si](C)(C)(C(C)(C)C)N([Si](C)(C)C(C)(C)C)[SiH2]C=CC GXOWWGBQEWDONC-UHFFFAOYSA-N 0.000 description 1
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 description 1
- DVNPFNZTPMWRAX-UHFFFAOYSA-N 2-triethoxysilylethanethiol Chemical compound CCO[Si](CCS)(OCC)OCC DVNPFNZTPMWRAX-UHFFFAOYSA-N 0.000 description 1
- LOSLJXKHQKRRFN-UHFFFAOYSA-N 2-trimethoxysilylethanethiol Chemical compound CO[Si](OC)(OC)CCS LOSLJXKHQKRRFN-UHFFFAOYSA-N 0.000 description 1
- XYKNGYCQUIQASK-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)propyl-(dimethoxymethyl)silane Chemical compound C1=CC=C2SC(CCC[SiH2]C(OC)OC)=NC2=C1 XYKNGYCQUIQASK-UHFFFAOYSA-N 0.000 description 1
- IABJHLPWGMWHLX-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)propyl-trimethoxysilane Chemical compound C1=CC=C2SC(CCC[Si](OC)(OC)OC)=NC2=C1 IABJHLPWGMWHLX-UHFFFAOYSA-N 0.000 description 1
- QPISLCVEROXXQD-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yltetrasulfanyl)propyl-triethoxysilane Chemical compound C1=CC=C2SC(SSSSCCC[Si](OCC)(OCC)OCC)=NC2=C1 QPISLCVEROXXQD-UHFFFAOYSA-N 0.000 description 1
- HFGLXKZGFFRQAR-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yltetrasulfanyl)propyl-trimethoxysilane Chemical compound C1=CC=C2SC(SSSSCCC[Si](OC)(OC)OC)=NC2=C1 HFGLXKZGFFRQAR-UHFFFAOYSA-N 0.000 description 1
- BKCOOZIJJMZJLU-UHFFFAOYSA-N 3-(2-ethoxyethoxy)propyl-trimethoxysilane Chemical compound CCOCCOCCC[Si](OC)(OC)OC BKCOOZIJJMZJLU-UHFFFAOYSA-N 0.000 description 1
- CBPIBCDYLRRTOI-UHFFFAOYSA-N 3-(3-triethoxysilylpropyl)furan-2,5-dione Chemical compound CCO[Si](OCC)(OCC)CCCC1=CC(=O)OC1=O CBPIBCDYLRRTOI-UHFFFAOYSA-N 0.000 description 1
- GXDMUOPCQNLBCZ-UHFFFAOYSA-N 3-(3-triethoxysilylpropyl)oxolane-2,5-dione Chemical compound CCO[Si](OCC)(OCC)CCCC1CC(=O)OC1=O GXDMUOPCQNLBCZ-UHFFFAOYSA-N 0.000 description 1
- WLKSOUIARBCUFF-UHFFFAOYSA-N 3-(3-trimethoxysilylpropyl)furan-2,5-dione Chemical compound CO[Si](OC)(OC)CCCC1=CC(=O)OC1=O WLKSOUIARBCUFF-UHFFFAOYSA-N 0.000 description 1
- ZADOWCXTUZWAKL-UHFFFAOYSA-N 3-(3-trimethoxysilylpropyl)oxolane-2,5-dione Chemical compound CO[Si](OC)(OC)CCCC1CC(=O)OC1=O ZADOWCXTUZWAKL-UHFFFAOYSA-N 0.000 description 1
- LOOUJXUUGIUEBC-UHFFFAOYSA-N 3-(dimethoxymethylsilyl)propane-1-thiol Chemical compound COC(OC)[SiH2]CCCS LOOUJXUUGIUEBC-UHFFFAOYSA-N 0.000 description 1
- LKORWALJQUXHIQ-UHFFFAOYSA-N 3-(ethoxymethoxy)propyl-trimethoxysilane Chemical compound CCOCOCCC[Si](OC)(OC)OC LKORWALJQUXHIQ-UHFFFAOYSA-N 0.000 description 1
- CQWSKEQAPKFKGM-UHFFFAOYSA-N 3-[[bis(trimethylsilyl)amino]silylmethylidene]pentane Chemical compound C[Si](C)(C)N([Si](C)(C)C)[SiH2]C=C(CC)CC CQWSKEQAPKFKGM-UHFFFAOYSA-N 0.000 description 1
- BUZICZZQJDLXJN-UHFFFAOYSA-N 3-azaniumyl-4-hydroxybutanoate Chemical compound OCC(N)CC(O)=O BUZICZZQJDLXJN-UHFFFAOYSA-N 0.000 description 1
- SGHHJMNTTHMRDX-UHFFFAOYSA-N 3-butan-2-yloxypropyl(trimethoxy)silane Chemical compound CCC(C)OCCC[Si](OC)(OC)OC SGHHJMNTTHMRDX-UHFFFAOYSA-N 0.000 description 1
- UYMVUIBPDVEYKA-UHFFFAOYSA-N 3-butoxypropyl(trimethoxy)silane Chemical compound CCCCOCCC[Si](OC)(OC)OC UYMVUIBPDVEYKA-UHFFFAOYSA-N 0.000 description 1
- HBBBMMMSWKEHKC-UHFFFAOYSA-N 3-ethoxypropyl(trimethoxy)silane Chemical compound CCOCCC[Si](OC)(OC)OC HBBBMMMSWKEHKC-UHFFFAOYSA-N 0.000 description 1
- QWVSDLSUAFWNAV-UHFFFAOYSA-N 3-silylprop-2-ene-1,1-diol Chemical group OC(O)C=C[SiH3] QWVSDLSUAFWNAV-UHFFFAOYSA-N 0.000 description 1
- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 description 1
- URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-UHFFFAOYSA-N 0.000 description 1
- XDQWJFXZTAWJST-UHFFFAOYSA-N 3-triethoxysilylpropyl prop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C=C XDQWJFXZTAWJST-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- AKQWHIMDQYDQSR-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylthiirane-2-carboxylate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C1(C)CS1 AKQWHIMDQYDQSR-UHFFFAOYSA-N 0.000 description 1
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 1
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 1
- 238000004438 BET method Methods 0.000 description 1
- JMOSIEZLPMAFJI-UHFFFAOYSA-N C(C)(C)N(C(C)C)[SiH](C=CCC)N(C(C)C)C(C)C Chemical compound C(C)(C)N(C(C)C)[SiH](C=CCC)N(C(C)C)C(C)C JMOSIEZLPMAFJI-UHFFFAOYSA-N 0.000 description 1
- XMTZBYWCOBIJHY-UHFFFAOYSA-N C(C)(C)N(C(C)C)[SiH](C=CCCC)N(C(C)C)C(C)C Chemical compound C(C)(C)N(C(C)C)[SiH](C=CCCC)N(C(C)C)C(C)C XMTZBYWCOBIJHY-UHFFFAOYSA-N 0.000 description 1
- IXQBXDJRNKVIKN-UHFFFAOYSA-N C(C)N(C(C)C)[SiH](C=CCCC)N(CC)C(C)C Chemical compound C(C)N(C(C)C)[SiH](C=CCCC)N(CC)C(C)C IXQBXDJRNKVIKN-UHFFFAOYSA-N 0.000 description 1
- JPCHAYLGSVKGRK-UHFFFAOYSA-N C(C)N(C)[SiH](C=CC)N(CC)C Chemical compound C(C)N(C)[SiH](C=CC)N(CC)C JPCHAYLGSVKGRK-UHFFFAOYSA-N 0.000 description 1
- DMJHWWRZPPDBPZ-UHFFFAOYSA-N C(C)N(C)[SiH](C=CCC)N(CC)C Chemical compound C(C)N(C)[SiH](C=CCC)N(CC)C DMJHWWRZPPDBPZ-UHFFFAOYSA-N 0.000 description 1
- SZXIQBOBUOIREO-UHFFFAOYSA-N C(C)N(C)[SiH](C=CCCCC)N(CC)C Chemical compound C(C)N(C)[SiH](C=CCCCC)N(CC)C SZXIQBOBUOIREO-UHFFFAOYSA-N 0.000 description 1
- BSLYYOOGCHJASQ-UHFFFAOYSA-N C(C)N(CC)[SiH](C=CCCC)N(CC)CC Chemical compound C(C)N(CC)[SiH](C=CCCC)N(CC)CC BSLYYOOGCHJASQ-UHFFFAOYSA-N 0.000 description 1
- CNTSRNOKUZHWJD-UHFFFAOYSA-N C(C)N(CC)[SiH](C=CCOCC)N(CC)CC Chemical compound C(C)N(CC)[SiH](C=CCOCC)N(CC)CC CNTSRNOKUZHWJD-UHFFFAOYSA-N 0.000 description 1
- GERKIQLNCQDCFK-UHFFFAOYSA-N C(C)N(CCC)[SiH](C=CC)N(CC)CCC Chemical compound C(C)N(CCC)[SiH](C=CC)N(CC)CCC GERKIQLNCQDCFK-UHFFFAOYSA-N 0.000 description 1
- CPDGSOLMMBMFQJ-UHFFFAOYSA-N C(C)N(CCC)[SiH](C=CCCCC)N(CC)CCC Chemical compound C(C)N(CCC)[SiH](C=CCCCC)N(CC)CCC CPDGSOLMMBMFQJ-UHFFFAOYSA-N 0.000 description 1
- BHOWGTFYFBXMOG-UHFFFAOYSA-N C(CCC)N(CCC)[SiH](C=CC)N(CCCC)CCC Chemical compound C(CCC)N(CCC)[SiH](C=CC)N(CCCC)CCC BHOWGTFYFBXMOG-UHFFFAOYSA-N 0.000 description 1
- DSHNSHZISCZYJJ-UHFFFAOYSA-N C(CCC)N(CCC)[SiH](C=CCC)N(CCCC)CCC Chemical compound C(CCC)N(CCC)[SiH](C=CCC)N(CCCC)CCC DSHNSHZISCZYJJ-UHFFFAOYSA-N 0.000 description 1
- BJSPCVQFRDEOIF-UHFFFAOYSA-N C(CCC)N(CCC)[SiH](C=CCCCC)N(CCCC)CCC Chemical compound C(CCC)N(CCC)[SiH](C=CCCCC)N(CCCC)CCC BJSPCVQFRDEOIF-UHFFFAOYSA-N 0.000 description 1
- RFVYQWYNYFCXQL-UHFFFAOYSA-N C1=CC=CC2=CC([Li])=CC=C21 Chemical compound C1=CC=CC2=CC([Li])=CC=C21 RFVYQWYNYFCXQL-UHFFFAOYSA-N 0.000 description 1
- SXLPVOKGQWNWFD-UHFFFAOYSA-N CCO[Si](CC[S+]=C(N(C)C)SSSSC(N(C)C)=[S+]CC[Si](OCC)(OCC)OCC)(OCC)OCC Chemical compound CCO[Si](CC[S+]=C(N(C)C)SSSSC(N(C)C)=[S+]CC[Si](OCC)(OCC)OCC)(OCC)OCC SXLPVOKGQWNWFD-UHFFFAOYSA-N 0.000 description 1
- ZZOXWBGGPBLVNQ-UHFFFAOYSA-N CN(C)C(SSSSC(N(C)C)=[S+]CCC[SiH2]C(OC)OC)=[S+]CCC[SiH2]C(OC)OC Chemical compound CN(C)C(SSSSC(N(C)C)=[S+]CCC[SiH2]C(OC)OC)=[S+]CCC[SiH2]C(OC)OC ZZOXWBGGPBLVNQ-UHFFFAOYSA-N 0.000 description 1
- SKFGZHGVWONCTD-UHFFFAOYSA-N CN(C)C(SSSSC(N(C)C)=[S+]CCC[Si](OC)(OC)OC)=[S+]CCC[Si](OC)(OC)OC Chemical compound CN(C)C(SSSSC(N(C)C)=[S+]CCC[Si](OC)(OC)OC)=[S+]CCC[Si](OC)(OC)OC SKFGZHGVWONCTD-UHFFFAOYSA-N 0.000 description 1
- DDMOXZKQNIKRGV-UHFFFAOYSA-N CN(C)[SiH](C=CCCC)N(C)C Chemical compound CN(C)[SiH](C=CCCC)N(C)C DDMOXZKQNIKRGV-UHFFFAOYSA-N 0.000 description 1
- LWXDWMWJONYGML-UHFFFAOYSA-N CN(C)[SiH](C=CCOC)N(C)C Chemical compound CN(C)[SiH](C=CCOC)N(C)C LWXDWMWJONYGML-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000006237 Intermediate SAF Substances 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- JCSXFSMSUPBTKG-UHFFFAOYSA-N N-(2-butylhex-1-enylsilyl)-N-ethylethanamine Chemical compound C(C)N(CC)[SiH2]C=C(CCCC)CCCC JCSXFSMSUPBTKG-UHFFFAOYSA-N 0.000 description 1
- LPRTXRXVYOGRSS-UHFFFAOYSA-N N-(2-butylhex-1-enylsilyl)-N-ethylpropan-1-amine Chemical compound C(C)N(CCC)[SiH2]C=C(CCCC)CCCC LPRTXRXVYOGRSS-UHFFFAOYSA-N 0.000 description 1
- ZNVKJMSBLDXXEB-UHFFFAOYSA-N N-(2-butylhex-1-enylsilyl)-N-ethylpropan-2-amine Chemical compound C(C)N(C(C)C)[SiH2]C=C(CCCC)CCCC ZNVKJMSBLDXXEB-UHFFFAOYSA-N 0.000 description 1
- KQEKDSPNJDBOTJ-UHFFFAOYSA-N N-(2-butylhex-1-enylsilyl)-N-methylethanamine Chemical compound C(C)N(C)[SiH2]C=C(CCCC)CCCC KQEKDSPNJDBOTJ-UHFFFAOYSA-N 0.000 description 1
- OHUNKWHWSAZYLY-UHFFFAOYSA-N N-(2-butylhex-1-enylsilyl)-N-methylmethanamine Chemical compound CN(C)[SiH2]C=C(CCCC)CCCC OHUNKWHWSAZYLY-UHFFFAOYSA-N 0.000 description 1
- BSVXVERXRWWBFK-UHFFFAOYSA-N N-(2-butylhex-1-enylsilyl)-N-propan-2-ylpropan-2-amine Chemical compound C(C)(C)N(C(C)C)[SiH2]C=C(CCCC)CCCC BSVXVERXRWWBFK-UHFFFAOYSA-N 0.000 description 1
- NIIWGFXXXVJYLF-UHFFFAOYSA-N N-(2-butylhex-1-enylsilyl)-N-propylbutan-1-amine Chemical compound C(CCC)N(CCC)[SiH2]C=C(CCCC)CCCC NIIWGFXXXVJYLF-UHFFFAOYSA-N 0.000 description 1
- BYPCYVWVWGPJBM-UHFFFAOYSA-N N-(2-ethylbut-1-enylsilyl)-N-methylethanamine Chemical compound C(C)N(C)[SiH2]C=C(CC)CC BYPCYVWVWGPJBM-UHFFFAOYSA-N 0.000 description 1
- PFFKLWLTKCZTCJ-UHFFFAOYSA-N N-(2-ethylbut-1-enylsilyl)-N-methylmethanamine Chemical compound CN(C)[SiH2]C=C(CC)CC PFFKLWLTKCZTCJ-UHFFFAOYSA-N 0.000 description 1
- KXFDZYMATUCRRH-UHFFFAOYSA-N N-(2-ethylbut-1-enylsilyl)-N-propan-2-ylpropan-2-amine Chemical compound C(C)(C)N(C(C)C)[SiH2]C=C(CC)CC KXFDZYMATUCRRH-UHFFFAOYSA-N 0.000 description 1
- WDXIYDNZVOFMFU-UHFFFAOYSA-N N-(2-ethylbut-1-enylsilyl)-N-propylbutan-1-amine Chemical compound C(CCC)N(CCC)[SiH2]C=C(CC)CC WDXIYDNZVOFMFU-UHFFFAOYSA-N 0.000 description 1
- LJLXNCSVWZLQJQ-UHFFFAOYSA-N N-(2-methylprop-1-enylsilyl)-N-propan-2-ylpropan-2-amine Chemical compound C(C)(C)N(C(C)C)[SiH2]C=C(C)C LJLXNCSVWZLQJQ-UHFFFAOYSA-N 0.000 description 1
- UKJRBHINPAZDKL-UHFFFAOYSA-N N-(2-methylprop-1-enylsilyl)-N-propylbutan-1-amine Chemical compound C(CCC)N(CCC)[SiH2]C=C(C)C UKJRBHINPAZDKL-UHFFFAOYSA-N 0.000 description 1
- FCIZFMMRSZRXHJ-UHFFFAOYSA-N N-(2-methylprop-1-enylsilyl)-N-propylpropan-1-amine Chemical compound C(CC)N(CCC)[SiH2]C=C(C)C FCIZFMMRSZRXHJ-UHFFFAOYSA-N 0.000 description 1
- FDTZELYNVHEOLS-UHFFFAOYSA-N N-(3,3-diethoxyprop-1-enylsilyl)-N-ethylethanamine Chemical compound C(C)N(CC)[SiH2]C=CC(OCC)OCC FDTZELYNVHEOLS-UHFFFAOYSA-N 0.000 description 1
- ANOSQJVWWPOJOQ-UHFFFAOYSA-N N-(3,3-diethoxyprop-1-enylsilyl)-N-methylmethanamine Chemical compound CN(C)[SiH2]C=CC(OCC)OCC ANOSQJVWWPOJOQ-UHFFFAOYSA-N 0.000 description 1
- DQVXYDLLNAUKBN-UHFFFAOYSA-N N-(3,3-dimethoxyprop-1-enylsilyl)-N-methylmethanamine Chemical compound CN(C)[SiH2]C=CC(OC)OC DQVXYDLLNAUKBN-UHFFFAOYSA-N 0.000 description 1
- NWUBOXRXWSLFOX-UHFFFAOYSA-N N-(4,4-diethoxybut-1-enylsilyl)-N-ethylethanamine Chemical compound C(C)N(CC)[SiH2]C=CCC(OCC)OCC NWUBOXRXWSLFOX-UHFFFAOYSA-N 0.000 description 1
- MRLOIESCLGCEEE-UHFFFAOYSA-N N-(4,4-diethoxybut-1-enylsilyl)-N-methylmethanamine Chemical compound CN(C)[SiH2]C=CCC(OCC)OCC MRLOIESCLGCEEE-UHFFFAOYSA-N 0.000 description 1
- IHDQKGLBJSIPIO-UHFFFAOYSA-N N-(4,4-dimethoxybut-1-enylsilyl)-N-ethylethanamine Chemical compound C(C)N(CC)[SiH2]C=CCC(OC)OC IHDQKGLBJSIPIO-UHFFFAOYSA-N 0.000 description 1
- SSCLYBHHCQIZSJ-UHFFFAOYSA-N N-(4,4-dimethoxybut-1-enylsilyl)-N-methylmethanamine Chemical compound CN(C)[SiH2]C=CCC(OC)OC SSCLYBHHCQIZSJ-UHFFFAOYSA-N 0.000 description 1
- JACAVCOKEXKMHH-UHFFFAOYSA-N N-[(dipropylamino)-hex-1-enylsilyl]-N-propylpropan-1-amine Chemical compound C(CC)N(CCC)[SiH](C=CCCCC)N(CCC)CCC JACAVCOKEXKMHH-UHFFFAOYSA-N 0.000 description 1
- ODVGXXCPNVVLNL-UHFFFAOYSA-N N-[(dipropylamino)-pent-1-enylsilyl]-N-propylpropan-1-amine Chemical compound C(CC)N(CCC)[SiH](C=CCCC)N(CCC)CCC ODVGXXCPNVVLNL-UHFFFAOYSA-N 0.000 description 1
- BZWHOGIEBKOASD-UHFFFAOYSA-N N-[[butyl(propyl)amino]-pent-1-enylsilyl]-N-propylbutan-1-amine Chemical compound C(CCC)N(CCC)[SiH](C=CCCC)N(CCCC)CCC BZWHOGIEBKOASD-UHFFFAOYSA-N 0.000 description 1
- JYPQUXUFICEUNV-UHFFFAOYSA-N N-[[di(propan-2-yl)amino]-hex-1-enylsilyl]-N-propan-2-ylpropan-2-amine Chemical compound C(C)(C)N(C(C)C)[SiH](C=CCCCC)N(C(C)C)C(C)C JYPQUXUFICEUNV-UHFFFAOYSA-N 0.000 description 1
- NQKCIEMFVOQKHX-UHFFFAOYSA-N N-[[di(propan-2-yl)amino]-prop-1-enylsilyl]-N-propan-2-ylpropan-2-amine Chemical compound C(C)(C)N(C(C)C)[SiH](C=CC)N(C(C)C)C(C)C NQKCIEMFVOQKHX-UHFFFAOYSA-N 0.000 description 1
- ICZQQAPOIQDAIS-UHFFFAOYSA-N N-[[ethyl(methyl)amino]-pent-1-enylsilyl]-N-methylethanamine Chemical compound C(C)N(C)[SiH](C=CCCC)N(CC)C ICZQQAPOIQDAIS-UHFFFAOYSA-N 0.000 description 1
- YWQYYKAOGYCIBI-UHFFFAOYSA-N N-[but-1-enyl(diethylamino)silyl]-N-ethylethanamine Chemical compound C(C)N(CC)[SiH](C=CCC)N(CC)CC YWQYYKAOGYCIBI-UHFFFAOYSA-N 0.000 description 1
- KCYYLSPCICQIBH-UHFFFAOYSA-N N-[but-1-enyl(dimethylamino)silyl]-N-methylmethanamine Chemical compound CN(C)[SiH](C=CCC)N(C)C KCYYLSPCICQIBH-UHFFFAOYSA-N 0.000 description 1
- BLJBDZBEHVSREZ-UHFFFAOYSA-N N-[but-1-enyl-(dibutylamino)silyl]-N-butylbutan-1-amine Chemical compound C(CCC)N(CCCC)[SiH](C=CCC)N(CCCC)CCCC BLJBDZBEHVSREZ-UHFFFAOYSA-N 0.000 description 1
- XHNXKUYXMCQYOZ-UHFFFAOYSA-N N-[but-1-enyl-(dipropylamino)silyl]-N-propylpropan-1-amine Chemical compound C(CC)N(CCC)[SiH](C=CCC)N(CCC)CCC XHNXKUYXMCQYOZ-UHFFFAOYSA-N 0.000 description 1
- LXSOOHBNENSUFC-UHFFFAOYSA-N N-[but-1-enyl-[ethyl(propan-2-yl)amino]silyl]-N-ethylpropan-2-amine Chemical compound C(C)N(C(C)C)[SiH](C=CCC)N(CC)C(C)C LXSOOHBNENSUFC-UHFFFAOYSA-N 0.000 description 1
- YCXUATGCLPIXPN-UHFFFAOYSA-N N-[but-1-enyl-[ethyl(propyl)amino]silyl]-N-ethylpropan-1-amine Chemical compound C(C)N(CCC)[SiH](C=CCC)N(CC)CCC YCXUATGCLPIXPN-UHFFFAOYSA-N 0.000 description 1
- IPSGSXZPWLRZDZ-UHFFFAOYSA-N N-[diethylamino(3-methoxyprop-1-enyl)silyl]-N-ethylethanamine Chemical compound C(C)N(CC)[SiH](C=CCOC)N(CC)CC IPSGSXZPWLRZDZ-UHFFFAOYSA-N 0.000 description 1
- WFMNSWHOEVVEDU-UHFFFAOYSA-N N-[diethylamino(4-ethoxybut-1-enyl)silyl]-N-ethylethanamine Chemical compound C(C)N(CC)[SiH](C=CCCOCC)N(CC)CC WFMNSWHOEVVEDU-UHFFFAOYSA-N 0.000 description 1
- WISROIVJSSJCSX-UHFFFAOYSA-N N-[diethylamino(4-methoxybut-1-enyl)silyl]-N-ethylethanamine Chemical compound C(C)N(CC)[SiH](C=CCCOC)N(CC)CC WISROIVJSSJCSX-UHFFFAOYSA-N 0.000 description 1
- IFBDAZRGAJQZRD-UHFFFAOYSA-N N-[diethylamino(hex-1-enyl)silyl]-N-ethylethanamine Chemical compound C(C)N(CC)[SiH](C=CCCCC)N(CC)CC IFBDAZRGAJQZRD-UHFFFAOYSA-N 0.000 description 1
- PHCFSXYKVJGGMB-UHFFFAOYSA-N N-[dimethylamino(3-ethoxyprop-1-enyl)silyl]-N-methylmethanamine Chemical compound CN(C)[SiH](C=CCOCC)N(C)C PHCFSXYKVJGGMB-UHFFFAOYSA-N 0.000 description 1
- KQUUEIIAAHCGHI-UHFFFAOYSA-N N-[dimethylamino(4-ethoxybut-1-enyl)silyl]-N-methylmethanamine Chemical compound CN(C)[SiH](C=CCCOCC)N(C)C KQUUEIIAAHCGHI-UHFFFAOYSA-N 0.000 description 1
- CJGHJOSTTCXULV-UHFFFAOYSA-N N-[dimethylamino(4-methoxybut-1-enyl)silyl]-N-methylmethanamine Chemical compound CN(C)[SiH](C=CCCOC)N(C)C CJGHJOSTTCXULV-UHFFFAOYSA-N 0.000 description 1
- MJKOEQDTQBYUSF-UHFFFAOYSA-N N-[dimethylamino(hex-1-enyl)silyl]-N-methylmethanamine Chemical compound CN(C)[SiH](C=CCCCC)N(C)C MJKOEQDTQBYUSF-UHFFFAOYSA-N 0.000 description 1
- AQQCLWZIELXFDV-UHFFFAOYSA-N N-[dimethylamino(prop-1-enyl)silyl]-N-methylmethanamine Chemical group CN(C)[SiH](C=CC)N(C)C AQQCLWZIELXFDV-UHFFFAOYSA-N 0.000 description 1
- VUFPOAHNHNSIBO-UHFFFAOYSA-N N-butyl-N-(2-butylhex-1-enylsilyl)butan-1-amine Chemical compound C(CCC)N(CCCC)[SiH2]C=C(CCCC)CCCC VUFPOAHNHNSIBO-UHFFFAOYSA-N 0.000 description 1
- KEIFEZJTCRKUSQ-UHFFFAOYSA-N N-butyl-N-(2-ethylbut-1-enylsilyl)butan-1-amine Chemical compound C(CCC)N(CCCC)[SiH2]C=C(CC)CC KEIFEZJTCRKUSQ-UHFFFAOYSA-N 0.000 description 1
- DRPMTNBURUYRIE-UHFFFAOYSA-N N-butyl-N-(2-methylprop-1-enylsilyl)butan-1-amine Chemical compound C(CCC)N(CCCC)[SiH2]C=C(C)C DRPMTNBURUYRIE-UHFFFAOYSA-N 0.000 description 1
- CCCFLJFCLCSVFL-UHFFFAOYSA-N N-butyl-N-(2-propylpent-1-enylsilyl)butan-1-amine Chemical compound C(CCC)N(CCCC)[SiH2]C=C(CCC)CCC CCCFLJFCLCSVFL-UHFFFAOYSA-N 0.000 description 1
- IIQDHZVEXIWRLE-UHFFFAOYSA-N N-butyl-N-[(dibutylamino)-hex-1-enylsilyl]butan-1-amine Chemical compound C(CCC)N(CCCC)[SiH](C=CCCCC)N(CCCC)CCCC IIQDHZVEXIWRLE-UHFFFAOYSA-N 0.000 description 1
- CVDYKLPAXWYWMK-UHFFFAOYSA-N N-butyl-N-[(dibutylamino)-pent-1-enylsilyl]butan-1-amine Chemical compound C(CCC)N(CCCC)[SiH](C=CCCC)N(CCCC)CCCC CVDYKLPAXWYWMK-UHFFFAOYSA-N 0.000 description 1
- ODGMPHOXFSFTAE-UHFFFAOYSA-N N-ethyl-N-(2-ethylbut-1-enylsilyl)ethanamine Chemical compound C(C)N(CC)[SiH2]C=C(CC)CC ODGMPHOXFSFTAE-UHFFFAOYSA-N 0.000 description 1
- MCJWAPLDEIFJPC-UHFFFAOYSA-N N-ethyl-N-(2-ethylbut-1-enylsilyl)propan-1-amine Chemical compound C(C)N(CCC)[SiH2]C=C(CC)CC MCJWAPLDEIFJPC-UHFFFAOYSA-N 0.000 description 1
- BLQBRIVPIBJCMT-UHFFFAOYSA-N N-ethyl-N-(2-ethylbut-1-enylsilyl)propan-2-amine Chemical compound C(C)N(C(C)C)[SiH2]C=C(CC)CC BLQBRIVPIBJCMT-UHFFFAOYSA-N 0.000 description 1
- OCTHFCZOQHUXHH-UHFFFAOYSA-N N-ethyl-N-(2-methylprop-1-enylsilyl)ethanamine Chemical compound C(C)N(CC)[SiH2]C=C(C)C OCTHFCZOQHUXHH-UHFFFAOYSA-N 0.000 description 1
- QAJXZYJEEPZWJV-UHFFFAOYSA-N N-ethyl-N-(2-methylprop-1-enylsilyl)propan-1-amine Chemical compound C(C)N(CCC)[SiH2]C=C(C)C QAJXZYJEEPZWJV-UHFFFAOYSA-N 0.000 description 1
- VYXCAPVLTJVYJK-UHFFFAOYSA-N N-ethyl-N-(2-methylprop-1-enylsilyl)propan-2-amine Chemical compound C(C)N(C(C)C)[SiH2]C=C(C)C VYXCAPVLTJVYJK-UHFFFAOYSA-N 0.000 description 1
- URXXIVNUYFEDRQ-UHFFFAOYSA-N N-ethyl-N-(2-propylpent-1-enylsilyl)ethanamine Chemical compound C(C)N(CC)[SiH2]C=C(CCC)CCC URXXIVNUYFEDRQ-UHFFFAOYSA-N 0.000 description 1
- ABUKMYCCFVALTO-UHFFFAOYSA-N N-ethyl-N-(2-propylpent-1-enylsilyl)propan-1-amine Chemical compound C(C)N(CCC)[SiH2]C=C(CCC)CCC ABUKMYCCFVALTO-UHFFFAOYSA-N 0.000 description 1
- IJKKYVVJKIAEJF-UHFFFAOYSA-N N-ethyl-N-(2-propylpent-1-enylsilyl)propan-2-amine Chemical compound C(C)N(C(C)C)[SiH2]C=C(CCC)CCC IJKKYVVJKIAEJF-UHFFFAOYSA-N 0.000 description 1
- AYTWHHCQSMWNGI-UHFFFAOYSA-N N-ethyl-N-[[ethyl(propan-2-yl)amino]-hex-1-enylsilyl]propan-2-amine Chemical compound C(C)N(C(C)C)[SiH](C=CCCCC)N(CC)C(C)C AYTWHHCQSMWNGI-UHFFFAOYSA-N 0.000 description 1
- UNDWUFPTGJXVGV-UHFFFAOYSA-N N-ethyl-N-[[ethyl(propyl)amino]-pent-1-enylsilyl]propan-1-amine Chemical compound C(C)N(CCC)[SiH](C=CCCC)N(CC)CCC UNDWUFPTGJXVGV-UHFFFAOYSA-N 0.000 description 1
- KDKMJJRTZITCRZ-UHFFFAOYSA-N N-methyl-N-(2-methylprop-1-enylsilyl)ethanamine Chemical compound C(C)N(C)[SiH2]C=C(C)C KDKMJJRTZITCRZ-UHFFFAOYSA-N 0.000 description 1
- RNJUVQSLWIPHEO-UHFFFAOYSA-N N-methyl-N-(2-propylpent-1-enylsilyl)ethanamine Chemical compound C(C)N(C)[SiH2]C=C(CCC)CCC RNJUVQSLWIPHEO-UHFFFAOYSA-N 0.000 description 1
- NCFUUIKIEQZOCT-UHFFFAOYSA-N N-methyl-N-(2-propylpent-1-enylsilyl)methanamine Chemical compound CN(C)[SiH2]C=C(CCC)CCC NCFUUIKIEQZOCT-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- QLDDCCNFAQCNND-UHFFFAOYSA-N N-propan-2-yl-N-(2-propylpent-1-enylsilyl)propan-2-amine Chemical compound C(C)(C)N(C(C)C)[SiH2]C=C(CCC)CCC QLDDCCNFAQCNND-UHFFFAOYSA-N 0.000 description 1
- YDRBLKFVVWCPHV-UHFFFAOYSA-N N-propyl-N-(2-propylpent-1-enylsilyl)butan-1-amine Chemical compound C(CCC)N(CCC)[SiH2]C=C(CCC)CCC YDRBLKFVVWCPHV-UHFFFAOYSA-N 0.000 description 1
- DSPWVXMEZWQRBP-UHFFFAOYSA-N N-propyl-N-(2-propylpent-1-enylsilyl)propan-1-amine Chemical compound C(CC)N(CCC)[SiH2]C=C(CCC)CCC DSPWVXMEZWQRBP-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- MXDVGCZHSQBKMG-UHFFFAOYSA-N O1CCN(CC1)[SiH](C=CC)N1CCOCC1 Chemical compound O1CCN(CC1)[SiH](C=CC)N1CCOCC1 MXDVGCZHSQBKMG-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- VSVVZZQIUJXYQA-UHFFFAOYSA-N [3-(3-dodecylsulfanylpropanoyloxy)-2,2-bis(3-dodecylsulfanylpropanoyloxymethyl)propyl] 3-dodecylsulfanylpropanoate Chemical compound CCCCCCCCCCCCSCCC(=O)OCC(COC(=O)CCSCCCCCCCCCCCC)(COC(=O)CCSCCCCCCCCCCCC)COC(=O)CCSCCCCCCCCCCCC VSVVZZQIUJXYQA-UHFFFAOYSA-N 0.000 description 1
- NTYDXFVCCCPXRG-UHFFFAOYSA-N [Li]C(C)(C)CC(C)(C)C Chemical compound [Li]C(C)(C)CC(C)(C)C NTYDXFVCCCPXRG-UHFFFAOYSA-N 0.000 description 1
- NTVIBFNHMURTMP-UHFFFAOYSA-N [Li]CC=CC[Li] Chemical compound [Li]CC=CC[Li] NTVIBFNHMURTMP-UHFFFAOYSA-N 0.000 description 1
- SHJXVDAAVHAKFB-UHFFFAOYSA-N [Li]CCCCCCCCCC Chemical compound [Li]CCCCCCCCCC SHJXVDAAVHAKFB-UHFFFAOYSA-N 0.000 description 1
- 239000006230 acetylene black Substances 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- BBXUCUQMOVNFQV-UHFFFAOYSA-N bis(4,5-dihydro-1h-imidazol-2-yl)-ethenyl-methylsilane Chemical compound N=1CCNC=1[Si](C=C)(C)C1=NCCN1 BBXUCUQMOVNFQV-UHFFFAOYSA-N 0.000 description 1
- ILTZOIGISOYOOV-UHFFFAOYSA-N bis(azepan-1-yl)-ethenyl-methylsilane Chemical compound C1CCCCCN1[Si](C=C)(C)N1CCCCCC1 ILTZOIGISOYOOV-UHFFFAOYSA-N 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 239000006231 channel black Substances 0.000 description 1
- KWTSZCJMWHGPOS-UHFFFAOYSA-M chloro(trimethyl)stannane Chemical compound C[Sn](C)(C)Cl KWTSZCJMWHGPOS-UHFFFAOYSA-M 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000000701 coagulant Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 1
- PKKGKUDPKRTKLJ-UHFFFAOYSA-L dichloro(dimethyl)stannane Chemical compound C[Sn](C)(Cl)Cl PKKGKUDPKRTKLJ-UHFFFAOYSA-L 0.000 description 1
- 229920003244 diene elastomer Polymers 0.000 description 1
- ZMAPKOCENOWQRE-UHFFFAOYSA-N diethoxy(diethyl)silane Chemical compound CCO[Si](CC)(CC)OCC ZMAPKOCENOWQRE-UHFFFAOYSA-N 0.000 description 1
- GSYVJAOBRKCNOT-UHFFFAOYSA-N diethoxymethyl-[3-[3-(diethoxymethylsilyl)propyltetrasulfanyl]propyl]silane Chemical compound CCOC(OCC)[SiH2]CCCSSSSCCC[SiH2]C(OCC)OCC GSYVJAOBRKCNOT-UHFFFAOYSA-N 0.000 description 1
- VSYLGGHSEIWGJV-UHFFFAOYSA-N diethyl(dimethoxy)silane Chemical compound CC[Si](CC)(OC)OC VSYLGGHSEIWGJV-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- JRYKZUSRJQZKOY-UHFFFAOYSA-M dizinc octadecanoate oxygen(2-) Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)[O-].[Zn+2].[O-2].[Zn+2] JRYKZUSRJQZKOY-UHFFFAOYSA-M 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- IQSBKDJPSOMMRZ-UHFFFAOYSA-N ethenyl(methyl)silane Chemical compound C[SiH2]C=C IQSBKDJPSOMMRZ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000006232 furnace black Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 235000013847 iso-butane Nutrition 0.000 description 1
- UREYYHIKHPFJEA-UHFFFAOYSA-N lithium;1h-pyrrole Chemical compound [Li].C=1C=CNC=1 UREYYHIKHPFJEA-UHFFFAOYSA-N 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- RRFBKRFYFCJYFK-UHFFFAOYSA-N lithium;n,n-dimethylpropan-1-amine Chemical compound [Li+].CN(C)CC[CH2-] RRFBKRFYFCJYFK-UHFFFAOYSA-N 0.000 description 1
- DWNRISLZVCBTRN-UHFFFAOYSA-N lithium;piperidin-1-ide Chemical compound [Li]N1CCCCC1 DWNRISLZVCBTRN-UHFFFAOYSA-N 0.000 description 1
- SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 description 1
- XBEREOHJDYAKDA-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].CC[CH2-] XBEREOHJDYAKDA-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000005055 methyl trichlorosilane Substances 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- CDQWREDVZBTNEU-UHFFFAOYSA-N n-[bis(diethylamino)-ethenylsilyl]-n-ethylethanamine Chemical compound CCN(CC)[Si](C=C)(N(CC)CC)N(CC)CC CDQWREDVZBTNEU-UHFFFAOYSA-N 0.000 description 1
- WBVXRXLWILVPMX-UHFFFAOYSA-N n-[bis(dimethylamino)-ethenylsilyl]-n-methylmethanamine Chemical compound CN(C)[Si](C=C)(N(C)C)N(C)C WBVXRXLWILVPMX-UHFFFAOYSA-N 0.000 description 1
- CNUZNKGKACKDTE-UHFFFAOYSA-N n-[bis(dipropylamino)-ethenylsilyl]-n-propylpropan-1-amine Chemical compound CCCN(CCC)[Si](C=C)(N(CCC)CCC)N(CCC)CCC CNUZNKGKACKDTE-UHFFFAOYSA-N 0.000 description 1
- MANGBWHVCZUCCO-UHFFFAOYSA-N n-[bis[butyl(propyl)amino]-ethenylsilyl]-n-propylbutan-1-amine Chemical compound CCCCN(CCC)[Si](C=C)(N(CCC)CCCC)N(CCC)CCCC MANGBWHVCZUCCO-UHFFFAOYSA-N 0.000 description 1
- VVZWJYBBBQFKSR-UHFFFAOYSA-N n-[ethenyl(diethyl)silyl]-n-propylpropan-1-amine Chemical compound CCCN(CCC)[Si](CC)(CC)C=C VVZWJYBBBQFKSR-UHFFFAOYSA-N 0.000 description 1
- FHYTZITXNBWWNN-UHFFFAOYSA-N n-[ethenyl(dimethyl)silyl]-n-methylmethanamine Chemical compound CN(C)[Si](C)(C)C=C FHYTZITXNBWWNN-UHFFFAOYSA-N 0.000 description 1
- ZRQZPBXNRJHJTF-UHFFFAOYSA-N n-[ethenyl-bis[ethyl(methyl)amino]silyl]-n-methylethanamine Chemical compound CCN(C)[Si](C=C)(N(C)CC)N(C)CC ZRQZPBXNRJHJTF-UHFFFAOYSA-N 0.000 description 1
- YQSINIFBRWCTHO-UHFFFAOYSA-N n-[ethenyl-bis[ethyl(propyl)amino]silyl]-n-ethylpropan-1-amine Chemical compound CCCN(CC)[Si](C=C)(N(CC)CCC)N(CC)CCC YQSINIFBRWCTHO-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- RKTDYMCMXBYRGU-UHFFFAOYSA-N n-butyl-n-[(dibutylamino)-ethenyl-methylsilyl]butan-1-amine Chemical compound CCCCN(CCCC)[Si](C)(C=C)N(CCCC)CCCC RKTDYMCMXBYRGU-UHFFFAOYSA-N 0.000 description 1
- RAOYTBVFGGKPKG-UHFFFAOYSA-N n-methyl-n-(2-triethoxysilylethyl)acetamide Chemical compound CCO[Si](OCC)(OCC)CCN(C)C(C)=O RAOYTBVFGGKPKG-UHFFFAOYSA-N 0.000 description 1
- YSVWSPIZAAWEBR-UHFFFAOYSA-N n-methyl-n-(2-triethoxysilylethyl)propanamide Chemical compound CCO[Si](OCC)(OCC)CCN(C)C(=O)CC YSVWSPIZAAWEBR-UHFFFAOYSA-N 0.000 description 1
- ZPMDCFTYXXAWKD-UHFFFAOYSA-N n-methyl-n-(2-trimethoxysilylethyl)acetamide Chemical compound CO[Si](OC)(OC)CCN(C)C(C)=O ZPMDCFTYXXAWKD-UHFFFAOYSA-N 0.000 description 1
- QRVUJGHCYUDDGB-UHFFFAOYSA-N n-methyl-n-(2-trimethoxysilylethyl)propanamide Chemical compound CCC(=O)N(C)CC[Si](OC)(OC)OC QRVUJGHCYUDDGB-UHFFFAOYSA-N 0.000 description 1
- WZFBEHLZOVJRGY-UHFFFAOYSA-N n-methyl-n-(3-triethoxysilylpropyl)acetamide Chemical compound CCO[Si](OCC)(OCC)CCCN(C)C(C)=O WZFBEHLZOVJRGY-UHFFFAOYSA-N 0.000 description 1
- RSOQGAOPMJGECD-UHFFFAOYSA-N n-methyl-n-(3-trimethoxysilylpropyl)acetamide Chemical compound CO[Si](OC)(OC)CCCN(C)C(C)=O RSOQGAOPMJGECD-UHFFFAOYSA-N 0.000 description 1
- WRGOOHULDXJZRK-UHFFFAOYSA-N n-methyl-n-(triethoxysilylmethyl)acetamide Chemical compound CCO[Si](OCC)(OCC)CN(C)C(C)=O WRGOOHULDXJZRK-UHFFFAOYSA-N 0.000 description 1
- KTFLSJWHWYSJNF-UHFFFAOYSA-N n-methyl-n-(triethoxysilylmethyl)propanamide Chemical compound CCO[Si](OCC)(OCC)CN(C)C(=O)CC KTFLSJWHWYSJNF-UHFFFAOYSA-N 0.000 description 1
- LDTKKHAKHFHXAJ-UHFFFAOYSA-N n-methyl-n-(trimethoxysilylmethyl)acetamide Chemical compound CO[Si](OC)(OC)CN(C)C(C)=O LDTKKHAKHFHXAJ-UHFFFAOYSA-N 0.000 description 1
- KUGXDAILFIENCV-UHFFFAOYSA-N n-methyl-n-(trimethoxysilylmethyl)propanamide Chemical compound CCC(=O)N(C)C[Si](OC)(OC)OC KUGXDAILFIENCV-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- CAZVNFHXWQYGPD-UHFFFAOYSA-N oxolane;potassium Chemical compound [K].C1CCOC1 CAZVNFHXWQYGPD-UHFFFAOYSA-N 0.000 description 1
- LGOPTUPXVVNJFH-UHFFFAOYSA-N pentadecanethioic s-acid Chemical compound CCCCCCCCCCCCCCC(O)=S LGOPTUPXVVNJFH-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 125000005353 silylalkyl group Chemical group 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- QLUMLEDLZDMGDW-UHFFFAOYSA-N sodium;1h-naphthalen-1-ide Chemical compound [Na+].[C-]1=CC=CC2=CC=CC=C21 QLUMLEDLZDMGDW-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229920003048 styrene butadiene rubber 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
- 238000010059 sulfur vulcanization Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- 239000006234 thermal black Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-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
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- RWJUTPORTOUFDY-UHFFFAOYSA-N triethoxy-[2-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CCO[Si](OCC)(OCC)CCOCC1CO1 RWJUTPORTOUFDY-UHFFFAOYSA-N 0.000 description 1
- QZUTWXSGNMUZBM-UHFFFAOYSA-N triethoxy-[2-(oxolan-2-ylmethoxy)ethyl]silane Chemical compound CCO[Si](OCC)(OCC)CCOCC1CCCO1 QZUTWXSGNMUZBM-UHFFFAOYSA-N 0.000 description 1
- MISUCTGXHWAUER-UHFFFAOYSA-N triethoxy-[3-(2-ethoxyethoxy)propyl]silane Chemical compound CCOCCOCCC[Si](OCC)(OCC)OCC MISUCTGXHWAUER-UHFFFAOYSA-N 0.000 description 1
- VQFCQIBNDODVOM-UHFFFAOYSA-N triethoxy-[3-(2-methoxyethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCCOC VQFCQIBNDODVOM-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
- KLFNHRIZTXWZHT-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltrisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSCCC[Si](OCC)(OCC)OCC KLFNHRIZTXWZHT-UHFFFAOYSA-N 0.000 description 1
- NSAGBLCZIZOQLH-UHFFFAOYSA-N triethoxy-[3-(ethoxymethoxy)propyl]silane Chemical compound CCOCOCCC[Si](OCC)(OCC)OCC NSAGBLCZIZOQLH-UHFFFAOYSA-N 0.000 description 1
- OMHOCEUKGBUUBP-UHFFFAOYSA-N triethoxy-[3-(methoxymethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCOC OMHOCEUKGBUUBP-UHFFFAOYSA-N 0.000 description 1
- VNMQOCYXFWAWMZ-UHFFFAOYSA-N triethoxy-[3-(oxolan-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CCCO1 VNMQOCYXFWAWMZ-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- VHXAXVOGSZEZKH-UHFFFAOYSA-N trimethoxy(3-propan-2-yloxypropyl)silane Chemical compound CO[Si](OC)(OC)CCCOC(C)C VHXAXVOGSZEZKH-UHFFFAOYSA-N 0.000 description 1
- NLSFXUALGZKXNV-UHFFFAOYSA-N trimethoxy(3-propoxypropyl)silane Chemical compound CCCOCCC[Si](OC)(OC)OC NLSFXUALGZKXNV-UHFFFAOYSA-N 0.000 description 1
- JSXKIRYGYMKWSK-UHFFFAOYSA-N trimethoxy-[2-(2-trimethoxysilylethyltetrasulfanyl)ethyl]silane Chemical compound CO[Si](OC)(OC)CCSSSSCC[Si](OC)(OC)OC JSXKIRYGYMKWSK-UHFFFAOYSA-N 0.000 description 1
- ZNXDCSVNCSSUNB-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CO[Si](OC)(OC)CCOCC1CO1 ZNXDCSVNCSSUNB-UHFFFAOYSA-N 0.000 description 1
- IWUSCXAORAAWIO-UHFFFAOYSA-N trimethoxy-[2-(oxolan-2-ylmethoxy)ethyl]silane Chemical compound CO[Si](OC)(OC)CCOCC1CCCO1 IWUSCXAORAAWIO-UHFFFAOYSA-N 0.000 description 1
- BJTBHSSNDGKAJO-UHFFFAOYSA-N trimethoxy-[3-(2-methoxyethoxy)propyl]silane Chemical compound COCCOCCC[Si](OC)(OC)OC BJTBHSSNDGKAJO-UHFFFAOYSA-N 0.000 description 1
- JTTSZDBCLAKKAY-UHFFFAOYSA-N trimethoxy-[3-(3-trimethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CO[Si](OC)(OC)CCCSSSSCCC[Si](OC)(OC)OC JTTSZDBCLAKKAY-UHFFFAOYSA-N 0.000 description 1
- YFFNIIAVGWYOQJ-UHFFFAOYSA-N trimethoxy-[3-(methoxymethoxy)propyl]silane Chemical compound COCOCCC[Si](OC)(OC)OC YFFNIIAVGWYOQJ-UHFFFAOYSA-N 0.000 description 1
- SAKLXMOLLSWVHU-UHFFFAOYSA-N trimethoxy-[3-[(2-methylpropan-2-yl)oxy]propyl]silane Chemical compound CO[Si](OC)(OC)CCCOC(C)(C)C SAKLXMOLLSWVHU-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L15/00—Compositions of rubber derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L7/00—Compositions of natural rubber
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/22—Incorporating nitrogen atoms into the molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/25—Incorporating silicon atoms into the molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
- C08C19/42—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups
- C08C19/44—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups of polymers containing metal atoms exclusively at one or both ends of the skeleton
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/42—Introducing metal atoms or metal-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
- C08L9/06—Copolymers with styrene
Definitions
- the present invention relates to a rubber composition and a pneumatic tire produced using the rubber composition.
- rubber compositions used for automobile tires are also required to have excellent fuel efficiency.
- rubber compositions for automobile tires rubber compositions containing conjugated diene polymers such as polybutadiene and butadiene-styrene copolymers and fillers such as carbon black and silica are used.
- Patent Document 1 proposes a method using a diene rubber modified with an organosilicon compound containing an amino group and an alkoxy group.
- the performance required for rubber compositions for automobile tires includes wet grip performance and wear resistance, but these performances are generally in contradiction to low fuel consumption. It was difficult to obtain a high dimension and good balance.
- An object of the present invention is to solve the above-mentioned problems and to provide a rubber composition that can improve fuel economy, wet grip performance, and wear resistance in a well-balanced manner, and a pneumatic tire using the same.
- the present invention is a conjugated diene polymer containing a rubber component and silica and having a structural unit based on a conjugated diene and a structural unit represented by the following formula (I) in 100% by mass of the rubber component.
- the content of the conjugated diene polymer obtained by modifying at least one end of the polymer with a silicon compound having a group represented by the following formula (II) and / or a group represented by the following formula (III) is 5% by mass: % Of the rubber component, and the silica content is 5 to 150 parts by mass with respect to 100 parts by mass of the rubber component.
- X 1 , X 2 and X 3 each independently represent a group represented by the following formula (Ia), a hydroxyl group, a hydrocarbyl group or a substituted hydrocarbyl group, and at least one of X 1 , X 2 and X 3 One is a group or a hydroxyl group represented by the following formula (Ia).
- R 1 and R 2 each independently represent a hydrocarbyl group having 1 to 6 carbon atoms, a substituted hydrocarbyl group having a carbon number of 1-6, a silyl group, or a substituted silyl group, R 1 and R 2 may be bonded to form a ring structure with the nitrogen atom.
- R 1 and R 2 in formula (Ia) are preferably hydrocarbyl groups having 1 to 6 carbon atoms.
- Two of X 1 , X 2 and X 3 in the formula (I) are preferably a group or a hydroxyl group represented by the formula (Ia).
- the silicon compound has a group represented by the following formula (IV). [Wherein R 3 , R 4 and R 5 each independently represents a hydrocarbyl group having 1 to 4 carbon atoms or a hydrocarbyloxy group having 1 to 4 carbon atoms, and R 3 , R 4 and R 5 At least one of 5 is a hydrocarbyloxy group. ]
- the silicon compound has a group represented by the following formula (IIa). [Wherein, m represents an integer of 1 to 10, and R 6 , R 7 and R 8 each independently represents a hydrocarbyl group having 1 to 4 carbon atoms or a hydrocarbyloxy group having 1 to 4 carbon atoms. And at least one of R 6 , R 7 and R 8 is a hydrocarbyloxy group. ]
- the vinyl bond content of the conjugated diene polymer is preferably 10 mol% or more and 80 mol% or less, with the content of the constituent unit based on the conjugated diene being 100 mol%.
- the rubber composition preferably contains natural rubber and / or butadiene rubber.
- the silica preferably has a nitrogen adsorption specific surface area of 40 to 400 m 2 / g.
- the rubber composition is preferably used as a tread rubber composition.
- the present invention also relates to a pneumatic tire produced using the rubber composition.
- the present invention since it is a rubber composition containing a specific conjugated diene polymer and silica, it is possible to provide a pneumatic tire with improved fuel economy, wet grip performance and wear resistance in a well-balanced manner. .
- the rubber composition of the present invention is a conjugated diene polymer having a structural unit based on a conjugated diene and a structural unit represented by the following formula (I), wherein the group represented by the following formula (II) and / or Alternatively, it includes a conjugated diene polymer in which at least one end of the polymer is modified with a silicon compound having a group represented by the following formula (III), and silica.
- X 1 , X 2 and X 3 each independently represent a group represented by the following formula (Ia), a hydroxyl group, a hydrocarbyl group or a substituted hydrocarbyl group, and at least one of X 1 , X 2 and X 3 One is a group or a hydroxyl group represented by the following formula (Ia).
- R 1 and R 2 each independently represent a hydrocarbyl group having 1 to 6 carbon atoms, a substituted hydrocarbyl group having a carbon number of 1-6, a silyl group, or a substituted silyl group, R 1 and R 2 may be bonded to form a ring structure with the nitrogen atom.
- conjugated diene based on the conjugated diene examples include 1,3-butadiene, isoprene, 1,3-pentadiene, 2,3-dimethyl-1,3-butadiene, 1,3-hexadiene, and the like. These may be one type or two or more types. From the viewpoint of availability, 1,3-butadiene and isoprene are preferred.
- X 1 , X 2 and X 3 in formula (I) of the structural unit represented by formula (I) each independently represent a group represented by formula (Ia), a hydroxyl group, a hydrocarbyl group or a substituted hydrocarbyl group.
- X 1 , X 2 and X 3 are a group represented by the formula (Ia) or a hydroxyl group.
- R 1 and R 2 of formula (Ia) represent each independently, a hydrocarbyl group having 1 to 6 carbon atoms, a substituted hydrocarbyl group having a carbon number of 1-6, a silyl group, or a substituted silyl group, R 1 And R 2 may be bonded together to form a ring structure together with the nitrogen atom.
- a hydrocarbyl group represents a hydrocarbon residue.
- the hydrocarbon residue represents a monovalent group obtained by removing hydrogen from a hydrocarbon.
- a substituted hydrocarbyl group represents a group in which one or more hydrogen atoms of a hydrocarbon residue are substituted with a substituent.
- the hydrocarbyloxy group represents a group in which a hydrogen atom of a hydroxyl group is substituted with a hydrocarbyl group
- the substituted hydrocarbyloxy group represents a group in which one or more hydrogen atoms of the hydrocarbyloxy group are substituted with a substituent.
- the substituted silyl group represents a group in which one or more hydrogen atoms of the silyl group are substituted with a substituent.
- Examples of the hydrocarbyl group having 1 to 6 carbon atoms in R 1 and R 2 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, n- Examples thereof include alkyl groups such as pentyl group, neopentyl group, isopentyl group and n-hexyl group; cycloalkyl groups such as cyclohexyl group; phenyl groups and the like.
- the substituted hydrocarbyl group having 1 to 6 carbon atoms in R 1 and R 2 is at least one group selected from the group consisting of a group having a nitrogen atom, a group having an oxygen atom, and a group having a silicon atom.
- the substituted hydrocarbyl group which has as a substituent can be mentioned.
- Examples of the group having a nitrogen atom group as a substituent include dialkylaminoalkyl groups such as a dimethylaminoethyl group and a diethylaminoethyl group.
- Examples of the group having an oxygen atom group as a substituent include methoxymethyl Group, methoxyethyl group, ethoxymethyl group, alkoxyalkyl group such as ethoxyethyl group, and the like.
- a silicon atom group as a substituent a trialkylsilylalkyl group such as trimethylsilylmethyl group, etc. Can be mentioned.
- Examples of the substituted silyl group for R 1 and R 2 include trialkylsilyl groups such as a trimethylsilyl group, a triethylsilyl group, and a t-butyldimethylsilyl group.
- the group to which R 1 and R 2 are bonded is a divalent group having 1 to 12 carbon atoms which may have at least one atom selected from the group consisting of a nitrogen atom, an oxygen atom and a silicon atom.
- Groups for example, an alkylene group such as a trimethylene group, a tetramethylene group, a pentamethylene group, or a hexamethylene group; an oxydialkylene group such as an oxydiethylene group or an oxydipropylene group; —CH 2 CH 2 —NH—CH 2 — And a nitrogen-containing group such as a group represented by —CH 2 CH 2 —N ⁇ CH—.
- the group to which R 1 and R 2 are bonded is preferably a nitrogen-containing group, a group represented by —CH 2 CH 2 —NH—CH 2 —, a group represented by —CH 2 CH 2 —N ⁇ CH—. Is more preferable.
- the hydrocarbyl group of R 1 and R 2 is preferably an alkyl group, more preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group, an ethyl group, an n-propyl group, or an n-butyl group. And the group n-butyl is particularly preferred.
- the substituted hydrocarbyl group for R 1 and R 2 is preferably an alkoxyalkyl group, more preferably an alkoxyalkyl group having 1 to 4 carbon atoms.
- the substituted silyl group for R 1 and R 2 is preferably a trialkylsilyl group, and more preferably a trimethylsilyl group.
- R 1 and R 2 are preferably an alkyl group, an alkoxyalkyl group, a substituted silyl group, or a nitrogen-containing group to which R 1 and R 2 are bonded, more preferably an alkyl group, still more preferably carbon. It is an alkyl group having 1 to 4 atoms, and more preferably a methyl group, an ethyl group, an n-propyl group, or an n-butyl group.
- Examples of the group represented by the formula (Ia) include an acyclic amino group and a cyclic amino group.
- acyclic amino group include dimethylamino group, diethylamino group, di (n-propyl) amino group, di (isopropyl) amino group, di (n-butyl) amino group, di (sec-butyl) amino group, di ( dialkylamino groups such as tert-butyl) amino group, di (neopentyl) amino group, ethylmethylamino group; di (methoxymethyl) amino group, di (methoxyethyl) amino group, di (ethoxymethyl) amino group, di ( And di (alkoxyalkyl) amino groups such as ethoxyethyl) amino group; and di (trialkylsilyl) amino groups such as di (trimethylsilyl) amino group and di (t-butyldimethylsilyl) amino group.
- Examples of the cyclic amino group include 1-pyrrolidinyl group, 1-piperidino group, 1-hexamethyleneimino group, 1-heptamethyleneimino group, 1-octamethyleneimino group, 1-decamethyleneimino group, 1-dodecamethyleneimino group. Mention may be made of 1-polymethyleneimino groups such as groups.
- Examples of the cyclic amino group include 1-imidazolyl group, 4,5-dihydro-1-imidazolyl group, 1-imidazolidinyl group, 1-piperazinyl group, morpholino group and the like.
- the group represented by the formula (Ia) is preferably an acyclic amino group, more preferably a dialkylamino group, and still more preferably a carbon atom number of 1 to 1, in view of economy and availability.
- Examples of the hydrocarbyl group of X 1 , X 2 and X 3 in the formula (I) include alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group and tert-butyl group. The group can be mentioned.
- examples of the substituted hydrocarbyl group include alkoxyalkyl groups such as a methoxymethyl group, an ethoxymethyl group, a methoxyethyl group, and an ethoxyethyl group.
- the hydrocarbyl group of X 1 , X 2 and X 3 is preferably an alkyl group, more preferably an alkyl group having 1 to 4 carbon atoms, and still more preferably a methyl group or an ethyl group.
- the substituted hydrocarbyl group of X 1 , X 2 and X 3 is preferably an alkoxyalkyl group, more preferably an alkoxyalkyl group having 1 to 4 carbon atoms.
- the hydrocarbyl group and substituted hydrocarbyl group of X 1 , X 2 and X 3 are preferably an alkyl group or an alkoxyalkyl group, more preferably an alkyl group having 1 to 4 carbon atoms or a carbon atom number of 1
- An alkoxyalkyl group having 4 to 4 more preferably an alkyl group having 1 to 4 carbon atoms, and still more preferably a methyl group or an ethyl group.
- At least one of X 1 , X 2 and X 3 in the formula (I) is a group or a hydroxyl group represented by the formula (Ia).
- X 1 , X 2 and X 3 are a group or a hydroxyl group represented by the formula (Ia), more preferably two of X 1 , X 2 and X 3 are represented by the formula (Ia ) Or a hydroxyl group.
- At least one of X 1 , X 2, and X 3 is a hydroxyl group from the viewpoint that low fuel consumption, wet grip performance, and wear resistance can be obtained in a high-order and well-balanced manner, and X 1 , X 2 and It is more preferable that two or more of X 3 are hydroxyl groups, and it is still more preferable that two of X 1 , X 2 and X 3 are hydroxyl groups.
- X 1 , X 2 and X 3 are acyclic amino groups or hydroxyl groups.
- a structural unit is preferred.
- X 1 , X 2 and X 3 are acyclic amino groups
- bis (dialkylamino) alkylvinylsilane units are preferred, bis (dimethylamino) methylvinylsilane units, bis (diethylamino) methylvinylsilane units, Bis (di (n-propyl) amino) methylvinylsilane units and bis (di (n-butyl) amino) methylvinylsilane units are more preferred.
- X 1 , X 2 and X 3 are hydroxyl groups
- a dihydroxyalkylvinylsilane unit is preferable, and a dihydroxymethylvinylsilane unit is more preferable.
- the content of the structural unit represented by the formula (I) in the conjugated diene polymer is preferably 0 per unit mass of the polymer from the viewpoint of improving fuel economy, wet grip performance and wear resistance in a balanced manner. It is 0.001 mmol / g polymer or more and 0.1 mmol / g polymer or less. More preferably, it is 0.002 mmol / g polymer or more and 0.07 mmol / g polymer or less. More preferably, it is 0.003 mmol / g polymer or more and 0.05 mmol / g polymer or less.
- the conjugated diene polymer is a polymer obtained by modifying at least one end of a polymer with a silicon compound having a group represented by the following formula (II) and / or a group represented by the following formula (III). .
- Examples of the group having a group represented by the formula (II) include an amide group, a carboxylic acid ester group, a methacryloyl group, and an acryloyl group.
- Examples of the group having a group represented by the formula (III) include oxydialkylene groups such as oxydimethylene group and oxydiethylene group; alkylene oxide groups such as epoxy group and tetrahydrofuranyl group.
- the alkylene oxide group represents a monovalent group obtained by removing a hydrogen atom from a ring of a cyclic ether compound.
- the silicon compound preferably has a group represented by the following formula (IV). [Wherein R 3 , R 4 and R 5 each independently represents a hydrocarbyl group having 1 to 4 carbon atoms or a hydrocarbyloxy group having 1 to 4 carbon atoms, and R 3 , R 4 and R 5 At least one of 5 is a hydrocarbyloxy group. ]
- the hydrocarbyl group of R 3 , R 4 and R 5 includes a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, and the like.
- An alkyl group etc. can be mentioned.
- Examples of the hydrocarbyloxy group of R 3 , R 4 and R 5 include alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, and t-butoxy group. Can be mentioned.
- the hydrocarbyl group of R 3 , R 4 and R 5 is preferably an alkyl group, more preferably an alkyl group having 1 to 3 carbon atoms, still more preferably a methyl group or an ethyl group.
- the hydrocarbyloxy group of R 3 , R 4 and R 5 is preferably an alkoxy group, more preferably an alkoxy group having 1 to 3 carbon atoms, still more preferably a methoxy group, ethoxy group It is a group.
- R 3 , R 4 and R 5 from the viewpoint of enhancing fuel economy, preferably at least two of R 3 , R 4 and R 5 are hydrocarbyloxy groups, and more preferably R 3 , R 4 and Three of R 5 are hydrocarbyloxy groups.
- Examples of the silicon compound having a group represented by the formula (II) and a group represented by the formula (IV) include a silicon compound having a group represented by the following formula (IIa).
- m represents an integer of 1 to 10
- R 6 , R 7 and R 8 each independently represents a hydrocarbyl group having 1 to 4 carbon atoms or a hydrocarbyloxy group having 1 to 4 carbon atoms.
- at least one of R 6 , R 7 and R 8 is a hydrocarbyloxy group.
- n represents an integer of 1 to 10. From the viewpoint of improving fuel economy, it is preferably 2 or more, and from the viewpoint of improving economy during production, it is preferably 4 or less. Particularly preferred is 3.
- Examples of the silicon compound having a group represented by the formula (IIa) include compounds represented by the following formula (IIb) or the following formula (IIc).
- n represents an integer of 1 to 10
- R 11 , R 12 and R 13 each independently represents a hydrocarbyl group having 1 to 4 carbon atoms or a hydrocarbyloxy group having 1 to 4 carbon atoms.
- R 14 and R 15 each independently represents a hydrocarbyl group having 1 to 10 carbon atoms, and 1 to 10 carbon atoms.
- a substituted hydrocarbyl group, a hydrocarbyloxy group having 1 to 10 carbon atoms or a substituted hydrocarbyloxy group having 1 to 10 carbon atoms, and R 14 and R 15 may be bonded to each other.
- R 21 to R 29 each independently represents a hydrocarbyl group having 1 to 4 carbon atoms or 1 carbon atom.
- R 21 , R 22 and R 23 is a hydrocarbyloxy group
- at least one of R 24 , R 25 and R 26 is a hydrocarbyloxy group
- R 27 , R 28 And at least one of R 29 is a hydrocarbyloxy group.
- N in the formula (IIb) represents an integer of 1 to 10. From the viewpoint of improving the fuel efficiency, wet grip performance and wear resistance in a balanced manner, it is preferably 2 or more, and preferably 4 or less from the viewpoint of improving economics during production. Particularly preferred is 3.
- examples of the hydrocarbyl group of R 11 , R 12 and R 13 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group.
- An alkyl group etc. can be mentioned.
- the hydrocarbyloxy group of R 11 , R 12 and R 13 is an alkoxy group such as a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group or a t-butoxy group. Can be mentioned.
- the hydrocarbyl group of R 11 , R 12 and R 13 is preferably an alkyl group, more preferably an alkyl group having 1 to 3 carbon atoms, still more preferably a methyl group or an ethyl group.
- the hydrocarbyloxy group of R 11 , R 12 and R 13 is preferably an alkoxy group, more preferably an alkoxy group having 1 to 3 carbon atoms, and still more preferably a methoxy group, ethoxy group It is a group.
- R 11 , R 12 and R 13 are preferably at least two of R 11 , R 12 and R 13 are hydrocarbyloxy groups from the viewpoint of improving the fuel economy, wet grip performance and wear resistance in a balanced manner. More preferably, three of R 11 , R 12 and R 13 are hydrocarbyloxy groups.
- Examples of the hydrocarbyl group of R 14 and R 15 include alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group.
- the substituted hydrocarbyl group of R 14 and R 15 is a substituted hydrocarbyl group having at least one group selected from the group consisting of a group having a nitrogen atom, a group having an oxygen atom and a group having a silicon atom as a substituent.
- a group having a nitrogen atom group as a substituent include dialkylaminoalkyl groups such as a dimethylaminoethyl group and a diethylaminoethyl group.
- Examples of the group having an oxygen atom group as a substituent include methoxymethyl Groups, methoxyethyl groups, ethoxymethyl groups, alkoxyalkyl groups such as ethoxyethyl groups, etc., and groups having silicon atoms as substituents include trialkylsilylmethyl groups, triethylsilylmethyl groups, etc.
- a silylalkyl group etc. can be mentioned.
- Examples of the hydrocarbyloxy group of R 14 and R 15 include alkoxy groups such as a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, and a t-butoxy group.
- Examples of the substituted hydrocarbyloxy group for R 14 and R 15 include alkoxyalkoxy groups such as a methoxymethoxy group, a methoxyethoxy group, an ethoxymethoxy group, and an ethoxyethoxy group.
- the group to which R 14 and R 15 are bonded is a divalent group having 2 to 12 carbon atoms which may have at least one atom selected from the group consisting of a nitrogen atom, an oxygen atom and a silicon atom.
- Groups for example, an alkylene group such as a trimethylene group, a tetramethylene group, a pentamethylene group, or a hexamethylene group; an oxydialkylene group such as an oxydiethylene group or an oxydipropylene group; —CH 2 CH 2 —NH—CH 2 — And a nitrogen-containing group such as a group represented by —CH 2 CH 2 —N ⁇ CH—.
- R 14 is preferably an alkyl group, more preferably an alkyl group having 1 to 4 carbon atoms, and still more preferably a methyl group or an ethyl group.
- R 15 is preferably an alkyl group, more preferably an alkyl group having 1 to 4 carbon atoms, and still more preferably a methyl group or an ethyl group.
- P, q and r in the formula (IIc) each independently represents an integer of 1 to 10. From the viewpoint of improving the fuel efficiency, wet grip performance and wear resistance in a balanced manner, it is preferably 2 or more, and preferably 4 or less from the viewpoint of improving economics during production. Particularly preferred is 3.
- examples of the hydrocarbyl group of R 21 to R 29 include alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group. Can be mentioned.
- examples of the hydrocarbyloxy group of R 21 to R 29 include alkoxy groups such as a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, and a t-butoxy group. Can do.
- the hydrocarbyl group of R 21 to R 29 is preferably an alkyl group, more preferably an alkyl group having 1 to 3 carbon atoms, and still more preferably a methyl group or an ethyl group. Further, the hydrocarbyloxy group of R 21 to R 29 is preferably an alkoxy group, more preferably an alkoxy group having 1 to 3 carbon atoms, and still more preferably a methoxy group or an ethoxy group. .
- R 21 , R 22 and R 23 preferably, at least two of R 21 , R 22 and R 23 are hydrocarbyloxy groups from the viewpoint of improving the fuel efficiency, wet grip performance and wear resistance in a balanced manner. More preferably, three of R 21 , R 22 and R 23 are hydrocarbyloxy groups.
- R 24 , R 25 and R 26 preferably, at least two of R 24 , R 25 and R 26 are hydrocarbyloxy groups from the viewpoint of improving the fuel economy, wet grip performance and wear resistance in a balanced manner. More preferably, three of R 24 , R 25 and R 26 are hydrocarbyloxy groups.
- R 27 , R 28 and R 29 are preferably at least two of R 27 , R 28 and R 29 are hydrocarbyloxy groups from the viewpoint of improving fuel economy, wet grip performance and wear resistance in a balanced manner. More preferably, three of R 27 , R 28 and R 29 are hydrocarbyloxy groups.
- N-alkyl-N-trialkoxysilylalkyl-substituted carboxylic acid amide More preferably, N-alkyl-N-trialkoxysilylalkyl-propionamide, More preferably, N-methyl-N- (3-trimethoxysilylpropyl) -propionamide, N-methyl-N- (3-triethoxysilylpropyl) -propionamide.
- the compound represented by the formula (IIc) preferably 1,3,5-tris (3-trimethoxysilylpropyl) isocyanurate, 1,3,5-tris (3-triethoxysilylpropyl) isocyanurate.
- Examples of the silicon compound having a group represented by the formula (III) and a group represented by the formula (IV) include a silicon compound represented by the following formula (IIIa).
- s represents an integer of 1 to 10
- R 31 , R 32 and R 33 each independently represents a hydrocarbyl group having 1 to 4 carbon atoms or a hydrocarbyloxy group having 1 to 4 carbon atoms.
- at least one of R 31 , R 32 and R 33 is a hydrocarbyloxy group
- R 34 represents a hydrocarbyl group having 1 to 10 carbon atoms or a substituted hydrocarbyl group having 1 to 10 carbon atoms.
- s represents an integer of 1 to 10. From the viewpoint of improving the fuel efficiency, wet grip performance and wear resistance in a balanced manner, it is preferably 2 or more, and preferably 4 or less from the viewpoint of improving economics during production. Particularly preferred is 3.
- examples of the hydrocarbyl group of R 31 , R 32 and R 33 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group.
- An alkyl group etc. can be mentioned.
- the hydrocarbyloxy group of R 31 , R 32 and R 33 is an alkoxy group such as a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group or a t-butoxy group. Can be mentioned.
- the hydrocarbyl group of R 31 , R 32 and R 33 is preferably an alkyl group, more preferably an alkyl group having 1 to 3 carbon atoms, still more preferably a methyl group or an ethyl group.
- the hydrocarbyloxy group of R 31 , R 32 and R 33 is preferably an alkoxy group, more preferably an alkoxy group having 1 to 3 carbon atoms, and still more preferably a methoxy group, ethoxy group It is a group.
- R 31 , R 32 and R 33 are preferably at least two of R 31 , R 32 and R 33 are hydrocarbyloxy groups from the viewpoint of improving fuel economy, wet grip performance and wear resistance in a balanced manner. More preferably, three of R 31 , R 32 and R 33 are hydrocarbyloxy groups.
- hydrocarbyl group of R 34 examples include alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, and tert-butyl group.
- Examples of the substituted hydrocarbyl group of R 34 include a substituted hydrocarbyl group having as a substituent at least one group selected from the group consisting of a group having a nitrogen atom, a group having an oxygen atom, and a group having a silicon atom. it can.
- Examples of the group having a nitrogen atom group as a substituent include dialkylaminoalkyl groups such as a dimethylaminoethyl group and a diethylaminoethyl group.
- Examples of the group having an oxygen atom group as a substituent include methoxymethyl Groups, methoxyethyl groups, ethoxymethyl groups, alkoxyalkyl groups such as ethoxyethyl groups; alkylene oxide alkyl groups such as glycidyl groups, tetrahydrofurfuryl groups, etc., and groups having silicon atom groups as substituents May include a trialkylsilylalkyl group such as a trimethylsilylmethyl group.
- the alkylene oxide alkyl group represents a group in which one or more hydrogen atoms of the alkyl group are substituted with an alkylene oxide group.
- R 34 is preferably an alkylene oxide alkyl group, more preferably a glycidyl group or a tetrahydrofurfuryl group.
- R 34 is an alkyl group
- 3- (methoxy) propyltrimethoxysilane, 3- (ethoxy) propyltrimethoxysilane, 3- (n-propoxy) propyltrimethoxysilane, 3- (isopropoxy) propyltrimethoxysilane, 3- (n-butoxy) propyltrimethoxysilane, 3- (sec-butoxy) propyltrimethoxysilane Mention may be made of 3- (alkoxy) propyltrialkoxysilanes such as 3- (t-butoxy) propyltrimethoxysilane.
- R 34 is an alkylene oxide alkyl group
- 2-glycidoxyethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 2-glycidoxyethyl triethoxysilane Glycidoxyalkyltrialkoxysilanes such as 3-glycidoxypropyltriethoxysilane; 2-tetrahydrofurfuryloxyethyltrimethoxysilane, 3-tetrahydrofurfuryloxypropyltrimethoxysilane, 2-tetrahydrofurfuryloxyethyl triethoxysilane, Mention may be made of tetrahydrofurfuryloxyalkyltrialkoxysilanes such as 3-tetrahydrofurfuroxylpropyl ethoxytriethoxysilane.
- R 34 is an alkoxyalkyl group
- the compound represented by the formula (IIIa) is preferably a compound in which R 34 is an alkylene oxide alkyl group, more preferably 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-tetrahydrofurfuryloxypropyltrimethoxysilane, 3-tetrahydrofurfuryloxypropyltriethoxysilane.
- Examples of the silicon compound having a group represented by the formula (II), a group represented by the formula (III), and a group represented by the formula (IV) include 3-acryloxyalkyltrialkoxysilane and 3-methacryloxyalkyltrialkoxysilane. Can be mentioned.
- Examples of the 3-acryloxyalkyltrialkoxysilane include 3-acryloxypropyltrialkoxysilane such as 3-acryloxypropyltrimethoxysilane and 3-acryloxypropyltriethoxysilane.
- Examples of the 3-methacryloxyalkyltrialkoxysilane include 3-methacryloxypropyltrialkoxysilane such as 3-methacryloxypropyltrimethoxysilane and 3-methacryloxypropyltriethoxysilane.
- Examples of the silicon compound having a group represented by the formula (II), a group represented by the formula (III), and a group represented by the formula (IV) include trialkoxysilylalkyl succinic anhydride and trialkoxysilylalkyl maleic anhydride. Can be mentioned.
- trialkoxysilylalkyl succinic anhydride examples include 3-trialkoxysilylpropyl succinic anhydride such as 3-trimethoxysilylpropyl succinic anhydride and 3-triethoxysilylpropyl succinic anhydride.
- trialkoxysilylalkyl maleic anhydride examples include 3-trialkoxysilylpropyl maleic anhydride such as 3-trimethoxysilylpropyl maleic anhydride and 3-triethoxysilylpropyl maleic anhydride.
- the conjugated diene polymer may have a constituent unit based on another monomer in addition to the constituent unit based on the conjugated diene (conjugated diene unit).
- the other monomer include aromatic vinyl, vinyl nitrile, and unsaturated carboxylic acid ester.
- the aromatic vinyl include styrene, ⁇ -methylstyrene, vinyl toluene, vinyl naphthalene, divinyl benzene, trivinyl benzene, and divinyl naphthalene.
- Examples of the vinyl nitrile include acrylonitrile, and examples of the unsaturated carboxylic acid ester include methyl acrylate, ethyl acrylate, methyl methacrylate, and ethyl methacrylate. Among these, aromatic vinyl is preferable, and styrene is more preferable.
- the conjugated diene polymer preferably has a structural unit based on aromatic vinyl (aromatic vinyl unit) from the viewpoint of wear resistance.
- the content of the aromatic vinyl unit is preferably a conjugated diene unit.
- the total amount of aromatic vinyl units is 100% by mass, preferably 10% by mass or more (conjugated diene unit content is 90% by mass or less), more preferably 15% by mass or more (conjugate diene unit content) Is 85% by mass or less).
- the content of the aromatic vinyl unit is preferably 50% by mass or less (the content of the conjugated diene unit is 50% by mass or more), more preferably 45% by mass or less (conjugated diene).
- the unit content is 55% by mass or more).
- the vinyl bond content of the conjugated diene polymer is preferably 80 mol% or less, more preferably 70 mol% or less from the viewpoint of fuel efficiency, with the content of the conjugated diene unit being 100 mol%. Moreover, from a viewpoint of wet grip performance, Preferably it is 10 mol% or more, More preferably, it is 15 mol% or more, More preferably, it is 20 mol% or more, Most preferably, it is 40 mol% or more.
- the vinyl bond amount is determined from the absorption intensity in the vicinity of 910 cm ⁇ 1, which is the absorption peak of the vinyl group, by infrared spectroscopy.
- the molecular weight distribution of the conjugated diene polymer is preferably 1 to 5 and more preferably 1 to 2 from the viewpoint of low fuel consumption.
- the molecular weight distribution is obtained by measuring the number average molecular weight (Mn) and the weight average molecular weight (Mw) by gel permeation chromatography (GPC) method and dividing Mw by Mn.
- Step A A monomer containing a conjugated diene and a vinyl compound represented by the following formula (V) is polymerized with an alkali metal catalyst in a hydrocarbon solvent, and a monomer unit based on the conjugated diene and A step of obtaining a polymer having an alkali metal derived from the catalyst at at least one end of a polymer chain having a monomer unit based on the vinyl compound represented by the formula (V).
- Step B A step of reacting the polymer obtained in Step A with a silicon compound having a group represented by the following formula (II) and / or a group represented by the following formula (III).
- Examples of the alkali metal catalyst used in (Step A) include an alkali metal, an organic alkali metal compound, a complex of an alkali metal and a polar compound, an oligomer having an alkali metal, and the like.
- Examples of the alkali metal include lithium, sodium, potassium, rubidium, cesium and the like.
- organic alkali metal compound examples include ethyl lithium, n-propyl lithium, iso-propyl lithium, n-butyl lithium, sec-butyl lithium, t-octyl lithium, n-decyl lithium, phenyl lithium, 2-naphthyl lithium, 2 -Butylphenyllithium, 4-phenylbutyllithium, cyclohexyllithium, 4-cyclopentyllithium, dimethylaminopropyllithium, diethylaminopropyllithium, t-butyldimethylsiloxypropyllithium, N-morpholinopropyllithium, lithium hexamethyleneimide, lithium pyrrole Zido, lithium piperidide, lithium heptamethylene imide, lithium dodecamethylene imide, 1,4-dilithio-2-butene, sodium naphthalenide, sodium Bifenirido, such as potassium napthalenide can be
- Examples of the complex of alkali metal and polar compound include potassium-tetrahydrofuran complex and potassium-diethoxyethane complex.
- Examples of the oligomer having alkali metal include sodium salt of ⁇ -methylstyrene tetramer. Can do. Among these, an organic lithium compound or an organic sodium compound is preferable, and an organic lithium compound or an organic sodium compound having 2 to 20 carbon atoms is more preferable.
- the hydrocarbon solvent used in (Step A) is a solvent that does not deactivate the organic alkali metal compound catalyst, and examples thereof include aliphatic hydrocarbons, aromatic hydrocarbons, and alicyclic hydrocarbons.
- examples of the aliphatic hydrocarbon include propane, n-butane, iso-butane, n-pentane, iso-pentane, n-hexane, propene, 1-butene, iso-butene, trans-2-butene, cis-2- Examples include butene, 1-pentene, 2-pentene, 1-hexene, and 2-hexene.
- examples of the aromatic hydrocarbon include benzene, toluene, xylene, and ethylbenzene
- examples of the alicyclic hydrocarbon include cyclopentane and cyclohexane. These may be used alone or in combination of two or more. Of these, hydrocarbons having 2 to 12 carbon atoms are preferable.
- a monomer containing a conjugated diene and a vinyl compound represented by the formula (V) is polymerized, and a conjugated diene polymer having an alkali metal derived from the above-mentioned alkali metal catalyst at the end of the polymer chain.
- the conjugated diene include 1,3-butadiene, isoprene, 1,3-pentadiene, 2,3-dimethyl-1,3-butadiene, and 1,3-hexadiene. Used in combination of more than one species. Of these, 1,3-butadiene and isoprene are preferred from the viewpoint of availability.
- X 4 , X 5 and X 6 in the formula (V) each independently represent a group represented by the formula (Va), a hydrocarbyl group or a substituted hydrocarbyl group, and at least one of X 4 , X 5 and X 6 Is a group represented by the formula (Va).
- R 9 and R 10 of formula (Va) each independently represent a hydrocarbyl group having 1 to 6 carbon atoms, a substituted hydrocarbyl group having a carbon number of 1-6, a silyl group, or a substituted silyl group, R 9 And R 10 may combine with each other to form a ring structure together with the nitrogen atom.
- Examples of the hydrocarbyl group having 1 to 6 carbon atoms of R 9 and R 10 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, n- Examples thereof include alkyl groups such as pentyl group, neopentyl group, isopentyl group and n-hexyl group; cycloalkyl groups such as cyclohexyl group; phenyl groups and the like.
- the substituted hydrocarbyl group having 1 to 6 carbon atoms in R 9 and R 10 is at least one group selected from the group consisting of a group having a nitrogen atom, a group having an oxygen atom, and a group having a silicon atom.
- the substituted hydrocarbyl group which has as a substituent can be mentioned.
- Examples of the group having a nitrogen atom group as a substituent include dialkylaminoalkyl groups such as a dimethylaminoethyl group and a diethylaminoethyl group.
- Examples of the group having an oxygen atom group as a substituent include methoxymethyl Group, methoxyethyl group, ethoxymethyl group, alkoxyalkyl group such as ethoxyethyl group, and the like.
- a silicon atom group as a substituent a trialkylsilylalkyl group such as trimethylsilylmethyl group, etc. Can be mentioned.
- Examples of the substituted silyl group for R 9 and R 10 include trialkylsilyl groups such as a trimethylsilyl group, a triethylsilyl group, and a t-butyldimethylsilyl group.
- the group to which R 9 and R 10 are bonded is a divalent group having 1 to 12 carbon atoms which may have at least one atom selected from the group consisting of a nitrogen atom, an oxygen atom and a silicon atom.
- Groups for example, an alkylene group such as a trimethylene group, a tetramethylene group, a pentamethylene group, or a hexamethylene group; an oxydialkylene group such as an oxydiethylene group or an oxydipropylene group; —CH 2 CH 2 —NH—CH 2 — And a nitrogen-containing group such as a group represented by —CH 2 CH 2 —N ⁇ CH—.
- the group to which R 9 and R 10 are bonded is preferably a nitrogen-containing group, a group represented by —CH 2 CH 2 —NH—CH 2 —, a group represented by —CH 2 CH 2 —N ⁇ CH—. Is more preferable.
- the hydrocarbyl group of R 9 and R 10 is preferably an alkyl group, more preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group, an ethyl group, an n-propyl group, or an n-butyl group. And the group n-butyl is particularly preferred.
- the substituted hydrocarbyl group for R 9 and R 10 is preferably an alkoxyalkyl group, more preferably an alkoxyalkyl group having 1 to 4 carbon atoms.
- the substituted silyl group for R 9 and R 10 is preferably a trialkylsilyl group, more preferably a trimethylsilyl group.
- R 9 and R 10 are preferably an alkyl group, an alkoxyalkyl group, a substituted silyl group, or a nitrogen-containing group to which R 9 and R 10 are bonded, more preferably an alkyl group, still more preferably carbon. It is an alkyl group having 1 to 4 atoms, and more preferably a methyl group, an ethyl group, an n-propyl group, or an n-butyl group.
- Examples of the group represented by the formula (Va) include an acyclic amino group and a cyclic amino group.
- acyclic amino group include dimethylamino group, diethylamino group, di (n-propyl) amino group, di (isopropyl) amino group, di (n-butyl) amino group, di (sec-butyl) amino group, di ( dialkylamino groups such as tert-butyl) amino group, di (neopentyl) amino group, ethylmethylamino group; di (methoxymethyl) amino group, di (methoxyethyl) amino group, di (ethoxymethyl) amino group, di ( And di (alkoxyalkyl) amino groups such as ethoxyethyl) amino group; and di (trialkylsilyl) amino groups such as di (trimethylsilyl) amino group and di (t-butyldimethylsilyl) amino group.
- Examples of the cyclic amino group include 1-pyrrolidinyl group, 1-piperidino group, 1-hexamethyleneimino group, 1-heptamethyleneimino group, 1-octamethyleneimino group, 1-decamethyleneimino group, 1-dodecamethyleneimino group. Mention may be made of 1-polymethyleneimino groups such as groups.
- Examples of the cyclic amino group include 1-imidazolyl group, 4,5-dihydro-1-imidazolyl group, 1-imidazolidinyl group, 1-piperazinyl group, morpholino group and the like.
- the group represented by the formula (Va) is preferably an acyclic amino group, more preferably a dialkylamino group, and still more preferably a carbon atom number of 1 to 1, in view of economy and availability.
- Examples of the hydrocarbyl group of X 4 , X 5 and X 6 in the formula (V) include alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group and tert-butyl group. The group can be mentioned.
- examples of the substituted hydrocarbyl group include alkoxyalkyl groups such as a methoxymethyl group, an ethoxymethyl group, a methoxyethyl group, and an ethoxyethyl group.
- the hydrocarbyl group of X 4 , X 5 and X 6 is preferably an alkyl group, more preferably an alkyl group having 1 to 4 carbon atoms, and still more preferably a methyl group or an ethyl group.
- the substituted hydrocarbyl group of X 4 , X 5 and X 6 is preferably an alkoxyalkyl group, more preferably an alkoxyalkyl group having 1 to 4 carbon atoms.
- the hydrocarbyl group and substituted hydrocarbyl group of X 4 , X 5 and X 6 are preferably an alkyl group or an alkoxyalkyl group, more preferably an alkyl group having 1 to 4 carbon atoms or a carbon atom number of 1
- An alkoxyalkyl group having 4 to 4 more preferably an alkyl group having 1 to 4 carbon atoms, and still more preferably a methyl group or an ethyl group.
- At least one of X 4 , X 5 and X 6 in the formula (V) is a group represented by the formula (Va).
- X 4 , X 5 and X 6 are groups represented by the formula (Va), more preferably two of X 4 , X 5 and X 6 are represented by the formula (Va). It is a group represented.
- one of X 4 , X 5 and X 6 is an acyclic amino group represented by the formula (Va), and two are hydrocarbyl groups.
- examples of the compound that is a substituted hydrocarbyl group include (dialkylamino) dialkylvinylsilane, ⁇ di (trialkylsilyl) amino ⁇ dialkylvinylsilane, (dialkylamino) dialkoxyalkylvinylsilane, and the like.
- (Dialkylamino) dialkylvinylsilanes include (dimethylamino) dimethylvinylsilane, (ethylmethylamino) dimethylvinylsilane, (diethylamino) dimethylvinylsilane, (ethyl-n-propylamino) dimethylvinylsilane, (ethylisopropylamino) dimethylvinylsilane, ( Di (n-propyl) amino) dimethylvinylsilane, (diisopropylamino) dimethylvinylsilane, (n-butyl-n-propylamino) dimethylvinylsilane, (di (n-butyl) amino) dimethylvinylsilane, (Dimethylamino) diethylvinylsilane, (ethylmethylamino) diethylvinylsilane, (diethylamino) diethyl
- ⁇ Di (trialkylsilyl) amino ⁇ dialkylvinylsilane includes ⁇ di (trimethylsilyl) amino ⁇ dimethylvinylsilane, ⁇ di (t-butyldimethylsilyl) amino ⁇ dimethylvinylsilane, ⁇ di (trimethylsilyl) amino ⁇ diethylvinylsilane, ⁇ di And (t-butyldimethylsilyl) amino ⁇ diethylvinylsilane.
- (Dialkylamino) dialkoxyalkylvinylsilane includes (dimethylamino) dimethoxymethylvinylsilane, (dimethylamino) dimethoxyethylvinylsilane, (dimethylamino) diethoxymethylvinylsilane, (dimethylamino) diethoxyethylvinylsilane, (diethylamino) dimethoxymethyl Examples include vinylsilane, (diethylamino) dimethoxyethylvinylsilane, (diethylamino) diethoxymethylvinylsilane, (diethylamino) diethoxyethylvinylsilane, and the like.
- X 4 , X 5 and X 6 are acyclic amino groups represented by the formula (Va) and one is a hydrocarbyl group or a substituted hydrocarbyl group, bis (dialkylamino) alkylvinylsilane, bis ⁇ di (Trialkylsilyl) amino ⁇ alkylvinylsilane, bis (dialkylamino) alkoxyalkylvinylsilane, and the like.
- Bis (dialkylamino) alkylvinylsilanes include bis (dimethylamino) methylvinylsilane, bis (ethylmethylamino) methylvinylsilane, bis (diethylamino) methylvinylsilane, bis (ethyl-n-propylamino) methylvinylsilane, and bis (ethylisopropyl).
- bis ⁇ di (trialkylsilyl) amino ⁇ alkylvinylsilane examples include bis ⁇ di (trimethylsilyl) amino ⁇ methylvinylsilane, bis ⁇ di (t-butyldimethylsilyl) amino ⁇ methylvinylsilane, bis ⁇ di (trimethylsilyl) amino ⁇ ethyl
- examples thereof include vinyl silane and bis ⁇ di (t-butyldimethylsilyl) amino ⁇ ethyl vinyl silane.
- bis (dialkylamino) alkoxyalkylvinylsilane examples include bis (dimethylamino) methoxymethylvinylsilane, bis (dimethylamino) methoxyethylvinylsilane, bis (dimethylamino) ethoxymethylvinylsilane, bis (dimethylamino) ethoxyethylvinylsilane, Examples thereof include bis (diethylamino) methoxymethylvinylsilane, bis (diethylamino) methoxyethylvinylsilane, bis (diethylamino) ethoxymethylvinylsilane, and bis (diethylamino) ethoxyethylvinylsilane.
- Examples of the compound in which three of X 4 , X 5 and X 6 are acyclic amino groups represented by the formula (Va) include tri (dialkylamino) vinylsilane.
- tri (dimethylamino) vinylsilane, tri (ethylmethylamino) vinylsilane, tri (diethylamino) vinylsilane, tri (ethylpropylamino) vinylsilane, tri (dipropylamino) vinylsilane, tri (butylpropylamino) vinylsilane Can do.
- Compounds in which two of X 4 , X 5 and X 6 are cyclic amino groups represented by the formula (Va) and one is a hydrocarbyl group or a substituted hydrocarbyl group include bis (morpholino) methylvinylsilane, bis (piperidino) methyl Examples thereof include vinyl silane, bis (4,5-dihydroimidazolyl) methyl vinyl silane, and bis (hexamethyleneimino) methyl vinyl silane.
- bis (diethylamino) methylvinylsilane and bis (di (n-butyl) amino) methylvinylsilane are preferable from the viewpoint of availability of the compound.
- polymerization may be performed by combining the conjugated diene and the vinyl compound represented by the formula (V) with another monomer.
- Other monomers include aromatic vinyl, vinyl nitrile, unsaturated carboxylic acid ester, and the like.
- aromatic vinyl include styrene, ⁇ -methylstyrene, vinyl toluene, vinyl naphthalene, divinyl benzene, trivinyl benzene, and divinyl naphthalene.
- vinyl nitrile include acrylonitrile
- examples of the unsaturated carboxylic acid ester include methyl acrylate, ethyl acrylate, methyl methacrylate, and ethyl methacrylate.
- aromatic vinyl is preferable, and styrene is more preferable.
- Polymerization in (Step A) is an agent that adjusts the vinyl bond amount of the conjugated diene unit, and an agent that adjusts the distribution of constituent units based on monomers other than the conjugated diene unit and the conjugated diene in the conjugated diene polymer chain. (Hereinafter collectively referred to as “regulator”) or the like.
- regulatory include ether compounds, tertiary amines, and phosphine compounds.
- the ether compound examples include cyclic ethers such as tetrahydrofuran, tetrahydropyran, and 1,4-dioxane; aliphatic monoethers such as diethyl ether and dibutyl ether; ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, and diethylene glycol diethyl ether. And aliphatic diethers such as diethylene glycol dibutyl ether; aromatic ethers such as diphenyl ether and anisole.
- cyclic ethers such as tetrahydrofuran, tetrahydropyran, and 1,4-dioxane
- aliphatic monoethers such as diethyl ether and dibutyl ether
- ethylene glycol dimethyl ether ethylene glycol diethyl ether
- ethylene glycol dibutyl ether ethylene glycol dibutyl ether
- Examples of the tertiary amine include triethylamine, tripropylamine, tributylamine, N, N, N ′, N′-tetramethylethylenediamine, N, N-diethylaniline, pyridine, quinoline and the like.
- Examples of the phosphine compound include trimethylphosphine, triethylphosphine, triphenylphosphine, and the like. These may be used alone or in combination of two or more.
- the polymerization temperature in (Step A) is usually 25 to 100 ° C., preferably 35 to 90 ° C. More preferably, it is 50 to 80 ° C.
- the polymerization time is usually 10 minutes to 5 hours.
- the amount of the silicon compound having the group represented by the formula (II) and / or the group represented by the formula (III) to be brought into contact with the polymer prepared in the step A is In terms of moles of silicon atoms, particularly silicon atoms having a group represented by formula (IV), it is usually 0.1 to 3 moles, preferably 0, per mole of alkali metal derived from the alkali metal catalyst. 0.5 to 2 mol, and more preferably 0.6 to 1.5 mol.
- the temperature at which the polymer prepared in Step A is brought into contact with the silicon compound having the group represented by Formula (II) and / or the group represented by Formula (III) is usually 25 to 100 ° C., preferably 35 to 90 ° C. More preferably, it is 50 to 80 ° C.
- the contact time is usually 60 seconds to 5 hours, preferably 5 minutes to 1 hour, more preferably 15 minutes to 1 hour.
- a coupling agent may be added to the hydrocarbon solution of the conjugated diene polymer in the polymerization termination from the start of polymerization of the monomer using an alkali metal catalyst, if necessary. Good.
- the coupling agent include compounds represented by the following formula (VI).
- R 41 a ML 4-a (VI) (Wherein R 41 represents an alkyl group, an alkenyl group, a cycloalkenyl group or an aromatic residue, M represents a silicon atom or a tin atom, L represents a halogen atom or a hydrocarbyloxy group, and a represents 0 to 2) Represents an integer.)
- the aromatic residue represents a monovalent group obtained by removing hydrogen bonded to an aromatic ring from an aromatic hydrocarbon.
- silicon tetrachloride methyltrichlorosilane, dimethyldichlorosilane, trimethylchlorosilane, tin tetrachloride, methyltrichlorotin, dimethyldichlorotin, trimethylchlorotin, tetramethoxysilane, methyl
- Examples include trimethoxysilane, dimethoxydimethylsilane, methyltriethoxysilane, ethyltrimethoxysilane, dimethoxydiethylsilane, diethoxydimethylsilane, tetraethoxysilane, ethyltriethoxysilane, and diethoxydiethylsilane.
- the addition amount of the coupling agent is preferably 0.03 mol or more, more preferably 0.05 mol or more, from the viewpoint of processability of the conjugated diene polymer per 1 mol of alkali metal derived from the alkali metal catalyst. is there. Moreover, from a viewpoint of low fuel consumption, Preferably it is 0.4 mol or less, More preferably, it is 0.3 mol or less.
- Conjugated diene polymers can be collected by known recovery methods, for example, (1) a method of adding a coagulant to a hydrocarbon solution of a conjugated diene polymer, and (2) adding steam to a hydrocarbon solution of a conjugated diene polymer.
- the conjugated diene polymer can be recovered from the hydrocarbon solution.
- the recovered conjugated diene polymer may be dried by a known dryer such as a band dryer or an extrusion dryer.
- the treatment may be performed in the state of the polymer alone or in the state of the composition as described below.
- Examples of the hydrolysis method include known methods such as a method by steam stripping.
- the above-described processing, the X 1, X 2 and X 3 of the formula (I) may be a hydroxyl group, fuel economy can be further improved in a balanced wet grip performance and abrasion resistance.
- the conjugated diene polymer can be used in the rubber composition of the present invention as a rubber component, and is preferably used in combination with other rubber components and additives.
- Examples of other rubber components include conventional styrene-butadiene copolymer rubber, polybutadiene rubber (BR), butadiene-isoprene copolymer rubber, and butyl rubber.
- natural rubber NR
- ethylene-propylene copolymer ethylene-octene copolymer and the like can also be mentioned. Two or more of these rubber components may be used in combination.
- it is preferable to use NR and / or BR and it is more preferable to use both components of NR and BR from the point that low-fuel-consumption property, wet grip performance, and abrasion resistance can be improved with good balance.
- the content of the conjugated diene polymer in 100% by mass of the rubber component is preferably 5% by mass or more, more preferably 10% by mass or more, still more preferably 30% by mass or more, and particularly preferably 50% by mass or more.
- the content of the conjugated diene polymer is preferably 90% by mass or less, more preferably 80% by mass or less, and still more preferably 70% by mass or less.
- the NR is not particularly limited.
- SIR20, RSS # 3, TSR20, deproteinized natural rubber (DPNR), high-purity natural rubber (HPNR), etc. which are common in the tire industry can be used.
- the content of NR in 100% by mass of the rubber component is preferably 5% by mass or more, more preferably 10% by mass or more, and further preferably 15% by mass or more. If it is less than 5% by mass, the wear resistance tends to decrease.
- the NR content is preferably 70% by mass or less, more preferably 60% by mass or less. If it exceeds 70% by mass, the wet grip performance tends to decrease.
- the BR is not particularly limited.
- BR1220 manufactured by Nippon Zeon Co., Ltd., BR130B manufactured by Ube Industries, Ltd., BR150B having a high cis content such as BR150B, VCR412 manufactured by Ube Industries, Ltd.
- Commonly used in the tire industry, such as BR containing syndiotactic polybutadiene crystals, can be used.
- the content of BR in 100% by mass of the rubber component is preferably 5% by mass or more, more preferably 10% by mass or more, and further preferably 15% by mass or more. If it is less than 5% by mass, the wear resistance tends to decrease.
- the BR content is preferably 60% by mass or less, more preferably 50% by mass or less. If it exceeds 60% by mass, the wet grip performance tends to decrease.
- the total content of NR and BR in 100% by mass of the rubber component is preferably 10% by mass or more, more preferably 20% by mass or more, and further preferably 30% by mass or more. If it is less than 10% by mass, the wear resistance tends to decrease.
- the total content is preferably 70% by mass or less, more preferably 50% by mass or less. If it exceeds 70% by mass, the wet grip performance tends to decrease.
- the rubber composition of the present invention is characterized by compounding silica as a reinforcing agent.
- the compounding amount (content) of the silica is preferably 5 to 150 parts by mass, more preferably 10 to 100 parts by mass with respect to 100 parts by mass of the rubber component.
- Silica may be used alone or in combination of two or more.
- the nitrogen adsorption specific surface area (N 2 SA) of the silica is preferably 40 to 400 m 2 / g, and more preferably 60 to 360 m 2 / g.
- Silica having a nitrogen adsorption specific surface area of less than 40 m 2 / g has a small reinforcing effect and tends to have low wear resistance, and silica having a nitrogen adsorption specific surface area of more than 400 m 2 / g has poor dispersibility, increases hysteresis loss, and lowers fuel efficiency.
- the nitrogen adsorption specific surface area of silica is a value measured by the BET method according to ASTM D3037-81.
- the content of silica in a total of 100% by mass of silica and carbon black is preferably 60% by mass or more, more preferably 85% by mass or more, preferably 98% by mass or less, more preferably 95% by mass or less. . If it is in the said range, low-fuel-consumption property, wet-grip performance, and abrasion resistance can be improved with a high dimension in a well-balanced manner.
- a silane coupling agent may be used in combination with the silica.
- silane coupling agents include bis (3-triethoxysilylpropyl) tetrasulfide, bis (3-triethoxysilylpropyl) trisulfide, bis (3-triethoxysilylpropyl) disulfide, and bis (2-triethoxy).
- Silylethyl) tetrasulfide bis (3-trimethoxysilylpropyl) tetrasulfide, bis (2-trimethoxysilylethyl) tetrasulfide, 3-mercaptopropyltrimethoxysilane, 3-mercaptopropyltriethoxysilane, 2-mercaptoethyl Trimethoxysilane, 2-mercaptoethyltriethoxysilane, 3-trimethoxysilylpropyl-N, N-dimethylthiocarbamoyl tetrasulfide, 3-triethoxysilylpropyl-N, N-dimethylthiocarb Moyl tetrasulfide, 2-triethoxysilylethyl-N, N-dimethylthiocarbamoyl tetrasulfide, 3-trimethoxysilylpropylbenzothiazole tetrasulfide
- silane coupling agents may be used alone or in combination of two or more.
- the compounding amount of the silane coupling agent is preferably 1 part by mass or more and more preferably 2 parts by mass or more with respect to 100 parts by mass of the silica. If the compounding amount of the silane coupling agent is less than 1 part by mass, the viscosity of the unvulcanized rubber composition tends to be high and the processability tends to be poor. Moreover, it is preferable that it is 20 mass parts or less with respect to 100 mass parts of said silica, and, as for the compounding quantity of a silane coupling agent, it is more preferable that it is 15 mass parts or less. When the compounding quantity of a silane coupling agent exceeds 20 mass parts, the compounding effect of the silane coupling agent as the compounding quantity will not be acquired, and there exists a tendency for cost to become high.
- additives can be used, such as sulfur vulcanizing agents; thiazole vulcanization accelerators, thiuram vulcanization accelerators, sulfenamide vulcanization accelerators, guanidine vulcanization accelerators.
- Vulcanization accelerators such as stearic acid and zinc oxide; organic peroxides; fillers such as carbon black, calcium carbonate, talc, alumina, clay, aluminum hydroxide, mica; silane coupling Agents; processing aids such as extender oils and lubricants; anti-aging agents can be exemplified.
- Examples of the carbon black include furnace black (furness carbon black) such as SAF, ISAF, HAF, MAF, FEF, SRF, GPF, APF, FF, CF, SCF and ECF; acetylene black (acetylene carbon black); FT and Examples thereof include thermal black (thermal carbon black) such as MT; channel black (channel carbon black) such as EPC, MPC and CC; graphite. These can be used alone or in combination of two or more.
- the content of carbon black is preferably 1 part by mass or more, more preferably 3 parts per 100 parts by mass of the rubber component from the viewpoint that fuel economy, wet grip performance and wear resistance can be improved in a high-dimensional and well-balanced manner. It is at least part by mass, preferably at most 30 parts by mass, more preferably at most 10 parts by mass.
- Nitrogen adsorption specific surface area (N 2 SA) of carbon black is usually 5 ⁇ 200m 2 / g, the lower limit is preferably 50 m 2 / g, the upper limit is 150 meters 2 / g.
- Carbon black has a dibutyl phthalate (DBP) absorption of usually 5 to 300 ml / 100 g, preferably a lower limit of 80 ml / 100 g and an upper limit of 180 ml / 100 g. If the N 2 SA or DBP absorption amount of the carbon black is less than the lower limit of the above range, the reinforcing effect tends to be small and the wear resistance tends to decrease.
- DBP dibutyl phthalate
- the extending oil examples include aromatic mineral oil (viscosity specific gravity constant (VGC value) 0.900 to 1.049), naphthenic mineral oil (VGC value 0.850 to 0.899), paraffinic mineral oil (VGC value 0.790 to 0.849), and the like.
- the polycyclic aromatic content of the extender oil is preferably less than 3% by mass, more preferably less than 1% by mass.
- the polycyclic aromatic content is measured according to the British Petroleum Institute 346/92 method.
- the aromatic compound content (CA) of the extending oil is preferably 20% by mass or more. These extending oils may be used in combination of two or more.
- vulcanization accelerator examples include thiazole vulcanization accelerators such as 2-mercaptobenzothiazole, dibenzothiazyl disulfide, and N-cyclohexyl-2-benzothiazylsulfenamide; tetramethylthiuram monosulfide, tetramethylthiuram Thiuram vulcanization accelerators such as disulfides; N-cyclohexyl-2-benzothiazole sulfenamide, Nt-butyl-2-benzothiazole sulfenamide, N-oxyethylene-2-benzothiazole sulfenamide, N -Sulfenamide vulcanization accelerators such as oxyethylene-2-benzothiazole sulfenamide, N, N'-diisopropyl-2-benzothiazole sulfenamide; diphenylguanidine, diortolylguanidine, orthotolylbiguanidine, etc. No Mention may
- a known method for example, using a known mixer such as a roll or a banbury for each component.
- a kneading method can be used.
- the kneading temperature is usually 50 to 200 ° C., preferably 80 to 190 ° C., and the kneading time is usually 30 seconds. -30 minutes, and preferably 1-30 minutes.
- the kneading temperature is usually 100 ° C. or lower, preferably room temperature to 80 ° C.
- a composition containing a vulcanizing agent and a vulcanization accelerator is usually used after vulcanization treatment such as press vulcanization.
- the vulcanization temperature is usually 120 to 200 ° C, preferably 140 to 180 ° C.
- the rubber composition of the present invention is excellent in the balance of low fuel consumption, wet grip performance and wear resistance, and can achieve a remarkable improvement effect of these performances.
- the rubber composition of the present invention can be suitably used for each member of a tire, and can be particularly suitably used for a tread.
- the pneumatic tire of the present invention is produced by a usual method using the rubber composition. That is, a rubber composition containing various additives as necessary is extruded in accordance with the shape of the tread of the tire at an unvulcanized stage, molded by a normal method on a tire molding machine, etc. The tire members are bonded together to form an unvulcanized tire. This unvulcanized tire can be heated and pressurized in a vulcanizer to produce the pneumatic tire of the present invention.
- the pneumatic tire of the present invention can be suitably used as a tire for passenger cars and a tire for trucks and buses (heavy load tire).
- Vinyl bond amount (unit: mol%) The amount of vinyl bonds in the polymer was determined from the absorption intensity near 910 cm ⁇ 1, which is the absorption peak of the vinyl group, by infrared spectroscopy.
- Styrene unit content (unit: mass%) According to JIS K6383 (1995), the content of styrene units in the polymer was determined from the refractive index.
- tan ⁇ A strip-shaped test piece having a width of 1 mm or 2 mm and a length of 40 mm was punched out of the sheet-like vulcanized rubber composition and subjected to the test. Using a spectrometer manufactured by Ueshima Seisakusho, tan ⁇ was measured at a dynamic strain amplitude of 1%, a frequency of 10 Hz, and a temperature of 50 ° C. The reciprocal value of tan ⁇ was expressed as an index with the reference comparative example being 100. The larger the value, the lower the rolling resistance and the lower the fuel consumption.
- Rolling resistance Using a rolling resistance tester, measure the rolling resistance when the test tire was run at a rim (15 ⁇ 6JJ), internal pressure (230 kPa), load (3.43 kN), speed (80 km / h). Indicated as an index when the reference comparative example is 100. A larger index is better (low fuel consumption).
- LAT abrasion test Using a LAT tester (Laboratory Abrasion and Skid Tester), the volume loss of each vulcanized rubber composition was measured under the conditions of a load of 50 N, a speed of 20 km / h, and a slip angle of 5 °.
- the numerical values (LAT index) in Tables 2 and 3 are relative values when the volume loss amount of the reference comparative example is 100. The larger the value, the better the wear resistance.
- Production Example 1 (Synthesis of Polymer 1) 5. The inside of a stainless steel polymerization reactor having an internal volume of 20 liters was washed, dried, and replaced with dry nitrogen, and hexane (specific gravity 0.68 g / cm 3 ) 10.2 kg, 1,3-butadiene 547 g, styrene 173 g, tetrahydrofuran 6. 1 ml and ethylene glycol diethyl ether 5.0 ml were charged into the polymerization reaction vessel.
- the obtained polymer solution was stirred at a stirring speed of 130 rpm, and 4.0 mmol of 1,3,5-tris (3-trimethoxysilylpropyl) isocyanurate was added and stirred for 15 minutes.
- 20 ml of hexane solution containing 0.80 ml of methanol was added to the polymer solution, and the polymer solution was further stirred for 5 minutes.
- the stirring speed was 130 rpm
- the temperature in the polymerization reactor was 65 ° C.
- the monomer was continuously fed into the polymerization reaction vessel.
- 14.4 mmol of bis (diethylamino) methylvinylsilane was added as a cyclohexane solution, and the mixture was charged into the polymerization reactor under the conditions of a stirring speed of 130 rpm and a polymerization reactor temperature of 65 ° C.
- the monomer was continuously fed into the polymerization reactor, and 1,3-butadiene and styrene were copolymerized for 0.5 hour.
- the stirring speed was 130 rpm, and the temperature in the polymerization reactor was 65 ° C.
- 14.4 mmol of bis (diethylamino) methylvinylsilane was added as a cyclohexane solution, and the mixture was charged into the polymerization reactor under the conditions of a stirring speed of 130 rpm and a polymerization reactor internal temperature of 65 ° C.
- the monomer was continuously fed into the polymerization reactor, and 1,3-butadiene and styrene were copolymerized for 0.5 hour.
- the stirring speed was 130 rpm, and the temperature in the polymerization reactor was 65 ° C.
- the amount of 1,3-butadiene supplied in the entire polymerization was 821 g, and the amount of styrene supplied was 259 g.
- the obtained polymer solution was stirred at a stirring rate of 130 rpm, and 3.6 mmol of 1,3,5-tris (3-trimethoxysilylpropyl) isocyanurate was added and stirred for 15 minutes.
- 20 ml of hexane solution containing 0.80 ml of methanol was added to the polymer solution, and the polymer solution was further stirred for 5 minutes.
- the stirring speed was 130 rpm
- the temperature in the polymerization reactor was 65 ° C.
- the monomer was continuously fed into the polymerization reaction vessel.
- the amount of 1,3-butadiene supplied was 205 g
- the amount of styrene supplied was 65 g.
- 2.8 mmol of bis (diethylamino) methylvinylsilane as a cyclohexane solution was added into the polymerization reactor under a stirring speed of 130 rpm and a polymerization reactor temperature of 65 ° C., and stirred for 30 minutes. did.
- 20 ml of a hexane solution containing 0.14 ml of methanol was put into the polymerization reactor, and the polymer solution was stirred for 5 minutes.
- the stirring rate was 130 rpm
- the temperature in the polymerization reactor was 65 ° C.
- copolymerization of 1,3-butadiene and styrene was carried out for 3 hours while continuously supplying the monomer into the polymerization reaction vessel.
- the amount of 1,3-butadiene supplied in the entire polymerization was 821 g
- the amount of styrene supplied was 259 g.
- the obtained polymer solution was stirred at a stirring speed of 130 rpm, and 4.0 mmol of 1,3,5-tris (3-trimethoxysilylpropyl) isocyanurate was added and stirred for 15 minutes.
- 20 ml of hexane solution containing 0.80 ml of methanol was added to the polymer solution, and the polymer solution was further stirred for 5 minutes.
- the stirring rate was 130 rpm, the temperature in the polymerization reactor was 65 ° C., and copolymerization of 1,3-butadiene and styrene was carried out for 3 hours while continuously supplying the monomer into the polymerization reaction vessel.
- the amount of 1,3-butadiene supplied in the entire polymerization was 821 g, and the amount of styrene supplied was 259 g.
- 20 ml of hexane solution containing 0.80 ml of methanol was added to the polymer solution, and the polymer solution was further stirred for 5 minutes.
- Production Example 7 (Synthesis of Polymer 7) 5. The inside of a stainless steel polymerization reactor having an internal volume of 20 liters was washed, dried, and replaced with dry nitrogen, and hexane (specific gravity 0.68 g / cm 3 ) 10.2 kg, 1,3-butadiene 547 g, styrene 173 g, tetrahydrofuran 6. 1 ml and ethylene glycol diethyl ether 5.0 ml were charged into the polymerization reaction vessel.
- the obtained polymer solution was stirred at a stirring speed of 130 rpm, and 4.0 mmol of 1,3,5-tris (3-trimethoxysilylpropyl) isocyanurate was added and stirred for 15 minutes.
- 20 ml of hexane solution containing 0.80 ml of methanol was added to the polymer solution, and the polymer solution was further stirred for 5 minutes.
- the evaluation results of the polymer 7 are shown in Table 1.
- the content of the structural unit represented by the formula (I) in the polymer calculated from the input amount and the supply amount of the raw material into the polymerization reactor is 0.009 mmol / g polymer per polymer unit mass. there were.
- Production Example 8 (Synthesis of Polymer 8) 5.
- the inside of a stainless steel polymerization reactor having an internal volume of 20 liters was washed, dried, and replaced with dry nitrogen, and hexane (specific gravity 0.68 g / cm 3 ) 10.2 kg, 1,3-butadiene 547 g, styrene 173 g, tetrahydrofuran 6.
- 1 ml and ethylene glycol diethyl ether 5.0 ml were charged into the polymerization reaction vessel.
- the obtained polymer solution was stirred at a stirring speed of 130 rpm, and 4.0 mmol of 3- (methoxy) propyltrimethoxysilane was added and stirred for 15 minutes.
- 20 ml of hexane solution containing 0.80 ml of methanol was added to the polymer solution, and the polymer solution was further stirred for 5 minutes.
- Natural rubber RSS # 3 Butadiene rubber: Ubepol BR150B manufactured by Ube Industries, Ltd.
- Polymers 1 to 8 Production examples 1 to 8 above Silica: Ultrasil VN3-G manufactured by Degussa (N 2 SA: 175 m 2 / g) Silane coupling agent: Si69 (bis (3-triethoxysilylpropyl) tetrasulfide) manufactured by Degussa Carbon black: Dia Black N339 manufactured by Mitsubishi Chemical Corporation (N 2 SA: 96 m 2 / g, DBP absorption: 124 ml / 100 g) Oil: X-140 manufactured by Japan Energy Co., Ltd.
- Anti-aging agent Antigen 3C manufactured by Sumitomo Chemical Co., Ltd.
- Stearic acid Beads manufactured by NOF Corporation
- Zinc oxide Zinc flower No. 1 manufactured by Mitsui Kinzoku Mining Co., Ltd.
- Wax Sunnock N manufactured by Ouchi Shinsei Chemical Co., Ltd.
- Sulfur Powder sulfur vulcanization accelerator manufactured by Tsurumi Chemical Industry Co., Ltd. 1: Soxinol CZ manufactured by Sumitomo Chemical Co., Ltd.
- Vulcanization accelerator 2 Soxinol D manufactured by Sumitomo Chemical Co., Ltd.
- Examples 1 to 7 and Comparative Examples 1 to 5 In accordance with the contents shown in Tables 2 and 3, materials other than sulfur and a vulcanization accelerator were kneaded for 5 minutes at 150 ° C. using a 1.7 L Banbury mixer manufactured by Kobe Steel, Ltd., and mixed. A kneaded paste was obtained. Next, sulfur and a vulcanization accelerator were added to the obtained kneaded product, and kneaded for 5 minutes under the condition of 80 ° C. using an open roll to obtain an unvulcanized rubber composition. The obtained unvulcanized rubber composition was press vulcanized with a 0.5 mm thick mold at 170 ° C. for 20 minutes to obtain a vulcanized rubber composition.
- the obtained unvulcanized rubber composition is molded into a tread shape and bonded together with other tire members on a tire molding machine to form an unvulcanized tire, which is vulcanized at 170 ° C. for 12 minutes, and tested.
- Tires (size: 195 / 65R15) were manufactured.
- the obtained vulcanized rubber composition and test tire were used for evaluation by the above test method.
- the test results are shown in Tables 2 and 3.
- the terminal is modified by a compound having a structural unit based on a conjugated diene and a structural unit represented by the above formula (I) and having a group represented by the above formula (II).
- the rubber compositions of Examples including the prepared polymers (Polymers 1, 2, 7, and 8) have a better balance of fuel efficiency, wet grip performance and wear resistance than the rubber compositions of Comparative Examples. Improved.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Tires In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
該非環状アミノ基としては、ジメチルアミノ基、ジエチルアミノ基、ジ(n-プロピル)アミノ基、ジ(イソプロピル)アミノ基、ジ(n-ブチル)アミノ基、ジ(sec-ブチル)アミノ基、ジ(tert-ブチル)アミノ基、ジ(ネオペンチル)アミノ基、エチルメチルアミノ基などのジアルキルアミノ基;ジ(メトキシメチル)アミノ基、ジ(メトキシエチル)アミノ基、ジ(エトキシメチル)アミノ基、ジ(エトキシエチル)アミノ基などのジ(アルコキシアルキル)アミノ基;ジ(トリメチルシリル)アミノ基、ジ(t-ブチルジメチルシリル)アミノ基などのジ(トリアルキルシリル)アミノ基などを挙げることができる。
なお、本明細書において、アルキレンオキシド基は、環状エーテル化合物の環から水素原子を除いた1価の基を表す。
N-メチル-N-(トリメトキシシリルメチル)-アセトアミド、
N-メチル-N-(トリエトキシシリルメチル)-アセトアミド、
N-メチル-N-(2-トリメトキシシリルエチル)-アセトアミド、
N-メチル-N-(2-トリエトキシシリルエチル)-アセトアミド、
N-メチル-N-(3-トリメトキシシリルプロピル)-アセトアミド、
N-メチル-N-(3-トリエトキシシリルプロピル)-アセトアミド
などのN-アルキル-N-トリアルコキシシリルアルキル-アセトアミド;
N-メチル-N-(トリメトキシシリルメチル)-プロピオンアミド、
N-メチル-N-(トリエトキシシリルメチル)-プロピオンアミド、
N-メチル-N-(2-トリメトキシシリルエチル)-プロピオンアミド、
N-メチル-N-(2-トリエトキシシリルエチル)-プロピオンアミド、
N-メチル-N-(3-トリメトキシシリルプロピル)-プロピオンアミド、
N-メチル-N-(3-トリエトキシシリルプロピル)-プロピオンアミド
などのN-アルキル-N-トリアルコキシシリルアルキル-プロピオンアミド等、
N-アルキル-N-トリアルコキシシリルアルキル置換カルボン酸アミドを挙げることができる。
N-アルキル-N-トリアルコキシシリルアルキル置換カルボン酸アミドであり、
より好ましくは、
N-アルキル-N-トリアルコキシシリルアルキル-プロピオンアミドであり、
更に好ましくは、
N-メチル-N-(3-トリメトキシシリルプロピル)-プロピオンアミド、
N-メチル-N-(3-トリエトキシシリルプロピル)-プロピオンアミドである。
1,3,5-トリス(3-トリメトキシシリルメチル)イソシアヌレート、
1,3,5-トリス(3-トリエトキシシリルメチル)イソシアヌレート、
1,3,5-トリス(3-トリメトキシシリルエチル)イソシアヌレート、
1,3,5-トリス(3-トリエトキシシリルエチル)イソシアヌレート、
1,3,5-トリス(3-トリメトキシシリルプロピル)イソシアヌレート、
1,3,5-トリス(3-トリエトキシシリルプロピル)イソシアヌレート
などの1,3,5-トリス(トリアルコキシアルキル)イソシアヌレートを挙げることができる。
1,3,5-トリス(3-トリメトキシシリルプロピル)イソシアヌレート、
1,3,5-トリス(3-トリエトキシシリルプロピル)イソシアヌレートである。
なお、本明細書において、アルキレンオキシドアルキル基は、アルキル基の1つ以上の水素原子がアルキレンオキシド基で置換されている基を表す。
R34がアルキル基である化合物として、
3-(メトキシ)プロピルトリメトキシシラン、
3-(エトキシ)プロピルトリメトキシシラン、
3-(n-プロポキシ)プロピルトリメトキシシラン、
3-(イソプロポキシ)プロピルトリメトキシシラン、
3-(n-ブトキシ)プロピルトリメトキシシラン、
3-(sec-ブトキシ)プロピルトリメトキシシラン、
3-(t-ブトキシ)プロピルトリメトキシシラン
などの3-(アルコキシ)プロピルトリアルコキシシランを挙げることができる。
2-グリシドキシエチルトリメトキシシラン、
3-グリシドキシプロピルトリメトキシシラン、
2-グリシドキシエチルトリエトキシシラン、
3-グリシドキシプロピルトリエトキシシラン
などのグリシドキシアルキルトリアルコキシシラン;
2-テトラヒドロフルフリロキシエチルトリメトキシシラン、
3-テトラヒドロフルフリロキシプロピルトリメトキシシラン、
2-テトラヒドロフルフリロキシエチルトリエトキシシラン、
3-テトラヒドロフルフリロキシプロピルトリエトキシシラン
などのテトラヒドロフルフリロキシアルキルトリアルコキシシランを挙げることができる。
3-(メトキシメトキシ)プロピルトリメトキシシラン、
3-(メトキシエトキシ)プロピルトリメトキシシラン、
3-(エトキシメトキシ)プロピルトリメトキシシラン、
3-(エトキシエトキシ)プロピルトリメトキシシラン、
3-(メトキシメトキシ)プロピルトリエトキシシラン、
3-(メトキシエトキシ)プロピルトリエトキシシラン、
3-(エトキシメトキシ)プロピルトリエトキシシラン、
3-(エトキシエトキシ)プロピルトリエトキシシラン
などの3-(アルコキシアルコキシ)プロピルトリアルコキシシランを挙げることができる。
3-グリシドキシプロピルトリメトキシシラン、
3-グリシドキシプロピルトリエトキシシラン、
3-テトラヒドロフルフリロキシプロピルトリメトキシシラン、
3-テトラヒドロフルフリロキシプロピルトリエトキシシランである。
3-メタクリロキシアルキルトリアルコキシシランとしては、3-メタクリロキシプロピルトリメトキシシラン、3-メタクリロキシプロピルトリエトキシシランなどの3-メタクリロキシプロピルトリアルコキシシランを挙げることができる。
トリアルコキシシリルアルキル無水マレイン酸としては、3-トリメトキシシリルプロピル無水マレイン酸、3-トリエトキシシリルプロピル無水マレイン酸などの3-トリアルコキシシリルプロピル無水マレイン酸を挙げることができる。
(工程A):炭化水素溶媒中で、アルカリ金属触媒により、共役ジエンと下式(V)で表されるビニル化合物とを含む単量体を重合させ、共役ジエンに基づく単量体単位と下式(V)で表されるビニル化合物に基づく単量体単位とを有する重合体鎖の少なくとも一端に、該触媒由来のアルカリ金属を有する重合体を得る工程。
(工程B):工程Aで得られた重合体と下式(II)で表される基及び/又は下式(III)で表される基を有するケイ素化合物とを反応させる工程。
該非環状アミノ基としては、ジメチルアミノ基、ジエチルアミノ基、ジ(n-プロピル)アミノ基、ジ(イソプロピル)アミノ基、ジ(n-ブチル)アミノ基、ジ(sec-ブチル)アミノ基、ジ(tert-ブチル)アミノ基、ジ(ネオペンチル)アミノ基、エチルメチルアミノ基などのジアルキルアミノ基;ジ(メトキシメチル)アミノ基、ジ(メトキシエチル)アミノ基、ジ(エトキシメチル)アミノ基、ジ(エトキシエチル)アミノ基などのジ(アルコキシアルキル)アミノ基;ジ(トリメチルシリル)アミノ基、ジ(t-ブチルジメチルシリル)アミノ基などのジ(トリアルキルシリル)アミノ基などを挙げることができる。
(ジアルキルアミノ)ジアルキルビニルシランとしては、(ジメチルアミノ)ジメチルビニルシラン、(エチルメチルアミノ)ジメチルビニルシラン、(ジエチルアミノ)ジメチルビニルシラン、(エチル-n-プロピルアミノ)ジメチルビニルシラン、(エチルイソプロピルアミノ)ジメチルビニルシラン、(ジ(n-プロピル)アミノ)ジメチルビニルシラン、(ジイソプロピルアミノ)ジメチルビニルシラン、(n-ブチル-n-プロピルアミノ)ジメチルビニルシラン、(ジ(n-ブチル)アミノ)ジメチルビニルシラン、
(ジメチルアミノ)ジエチルビニルシラン、(エチルメチルアミノ)ジエチルビニルシラン、(ジエチルアミノ)ジエチルビニルシラン、(エチル-n-プロピルアミノ)ジエチルビニルシラン、(エチルイソプロピルアミノ)ジエチルビニルシラン、(ジ(n-プロピル)アミノ)ジエチルビニルシラン、(ジイソプロピルアミノ)ジエチルビニルシラン、(n-ブチル-n-プロピルアミノ)ジエチルビニルシラン、(ジ(n-ブチル)アミノ)ジエチルビニルシラン、
(ジメチルアミノ)ジプロピルビニルシラン、(エチルメチルアミノ)ジプロピルビニルシラン、(ジエチルアミノ)ジプロピルビニルシラン、(エチル-n-プロピルアミノ)ジプロピルビニルシラン、(エチルイソプロピルアミノ)ジプロピルビニルシラン、(ジ(n-プロピル)アミノ)ジプロピルビニルシラン、(ジイソプロピルアミノ)ジプロピルビニルシラン、(n-ブチル-n-プロピルアミノ)ジプロピルビニルシラン、(ジ(n-ブチル)アミノ)ジプロピルビニルシラン、
(ジメチルアミノ)ジブチルビニルシラン、(エチルメチルアミノ)ジブチルビニルシラン、(ジエチルアミノ)ジブチルビニルシラン、(エチル-n-プロピルアミノ)ジブチルビニルシラン、(エチルイソプロピルアミノ)ジブチルビニルシラン、(ジ(n-プロピル)アミノ)ジブチルビニルシラン、(ジイソプロピルアミノ)ジブチルビニルシラン、(n-ブチル-n-プロピルアミノ)ジブチルビニルシラン、(ジ(n-ブチル)アミノ)ジブチルビニルシランなどを挙げることができる。
{ジ(トリアルキルシリル)アミノ}ジアルキルビニルシランとしては、{ジ(トリメチルシリル)アミノ}ジメチルビニルシラン、{ジ(t-ブチルジメチルシリル)アミノ}ジメチルビニルシラン、{ジ(トリメチルシリル)アミノ}ジエチルビニルシラン、{ジ(t-ブチルジメチルシリル)アミノ}ジエチルビニルシランなどを挙げることができる。
(ジアルキルアミノ)ジアルコキシアルキルビニルシランとしては、(ジメチルアミノ)ジメトキシメチルビニルシラン、(ジメチルアミノ)ジメトキシエチルビニルシラン、(ジメチルアミノ)ジエトキシメチルビニルシラン、(ジメチルアミノ)ジエトキシエチルビニルシラン、(ジエチルアミノ)ジメトキシメチルビニルシラン、(ジエチルアミノ)ジメトキシエチルビニルシラン、(ジエチルアミノ)ジエトキシメチルビニルシラン、(ジエチルアミノ)ジエトキシエチルビニルシランなどを挙げることができる。
ビス(ジアルキルアミノ)アルキルビニルシランとしては、ビス(ジメチルアミノ)メチルビニルシラン、ビス(エチルメチルアミノ)メチルビニルシラン、ビス(ジエチルアミノ)メチルビニルシラン、ビス(エチル-n-プロピルアミノ)メチルビニルシラン、ビス(エチルイソプロピルアミノ)メチルビニルシラン、ビス(ジ(n-プロピル)アミノ)メチルビニルシラン、ビス(ジイソプロピルアミノ)メチルビニルシラン、ビス(n-ブチル-n-プロピルアミノ)メチルビニルシラン、ビス(ジ(n-ブチル)アミノ)メチルビニルシラン、
ビス(ジメチルアミノ)エチルビニルシラン、ビス(エチルメチルアミノ)エチルビニルシラン、ビス(ジエチルアミノ)エチルビニルシラン、ビス(エチル-n-プロピルアミノ)エチルビニルシラン、ビス(エチルイソプロピルアミノ)エチルビニルシラン、ビス(ジ(n-プロピル)アミノ)エチルビニルシラン、ビス(ジイソプロピルアミノ)エチルビニルシラン、ビス(n-ブチル-n-プロピルアミノ)エチルビニルシラン、ビス(ジ(n-ブチル)アミノ)エチルビニルシラン、
ビス(ジメチルアミノ)プロピルビニルシラン、ビス(エチルメチルアミノ)プロピルビニルシラン、ビス(ジエチルアミノ)プロピルビニルシラン、ビス(エチル-n-プロピルアミノ)プロピルビニルシラン、ビス(エチルイソプロピルアミノ)プロピルビニルシラン、ビス(ジ(n-プロピル)アミノ)プロピルビニルシラン、ビス(ジイソプロピルアミノ)プロピルビニルシラン、ビス(n-ブチル-n-プロピルアミノ)プロピルビニルシラン、ビス(ジ(n-ブチル)アミノ)プロピルビニルシラン、
ビス(ジメチルアミノ)ブチルビニルシラン、ビス(エチルメチルアミノ)ブチルビニルシラン、ビス(ジエチルアミノ)ブチルビニルシラン、ビス(エチル-n-プロピルアミノ)ブチルビニルシラン、ビス(エチルイソプロピルアミノ)ブチルビニルシラン、ビス(ジ(n-プロピル)アミノ)ブチルビニルシラン、ビス(ジイソプロピルアミノ)ブチルビニルシラン、ビス(n-ブチル-n-プロピルアミノ)ブチルビニルシラン、ビス(ジ(n-ブチル)アミノ)ブチルビニルシランなどを挙げることができる。
ビス{ジ(トリアルキルシリル)アミノ}アルキルビニルシランとしては、ビス{ジ(トリメチルシリル)アミノ}メチルビニルシラン、ビス{ジ(t-ブチルジメチルシリル)アミノ}メチルビニルシラン、ビス{ジ(トリメチルシリル)アミノ}エチルビニルシラン、ビス{ジ(t-ブチルジメチルシリル)アミノ}エチルビニルシランなどを挙げることができる。
ビス(ジアルキルアミノ)アルコキシアルキルビニルシランとしては、ビス(ジメチルアミノ)メトキシメチルビニルシラン、ビス(ジメチルアミノ)メトキシエチルビニルシラン、ビス(ジメチルアミノ)エトキシメチルビニルシラン、ビス(ジメチルアミノ)エトキシエチルビニルシラン、
ビス(ジエチルアミノ)メトキシメチルビニルシラン、ビス(ジエチルアミノ)メトキシエチルビニルシラン、ビス(ジエチルアミノ)エトキシメチルビニルシラン、ビス(ジエチルアミノ)エトキシエチルビニルシランなどを挙げることができる。
例えば、トリ(ジメチルアミノ)ビニルシラン、トリ(エチルメチルアミノ)ビニルシラン、トリ(ジエチルアミノ)ビニルシラン、トリ(エチルプロピルアミノ)ビニルシラン、トリ(ジプロピルアミノ)ビニルシラン、トリ(ブチルプロピルアミノ)ビニルシランなどを挙げることができる。
R41 aML4-a(VI)
(式中、R41はアルキル基、アルケニル基、シクロアルケニル基または芳香族残基を表し、Mはケイ素原子またはスズ原子を表し、Lはハロゲン原子またはヒドロカルビルオキシ基を表し、aは0~2の整数を表す。)
ここで、芳香族残基は、芳香族炭化水素から芳香環に結合している水素を除いた1価の基を表す。
なお、シリカの窒素吸着比表面積は、ASTM D3037-81に準じてBET法で測定される値である。
加硫剤、加硫促進剤を配合する場合、混練温度は、通常100℃以下であり、好ましくは室温~80℃である。また、加硫剤、加硫促進剤を配合した組成物は、通常、プレス加硫などの加硫処理を行って用いられる。加硫温度としては、通常120~200℃、好ましくは140~180℃である。
物性評価は次の方法で行った。なお、以下の評価においては、実施例1~6及び比較例2~4は比較例1を基準比較例とし、実施例7は比較例5を基準比較例とした。
赤外分光分析法により、ビニル基の吸収ピークである910cm-1付近の吸収強度より重合体のビニル結合量を求めた。
JIS K6383(1995)に従って、屈折率から重合体のスチレン単位の含量を求めた。
下記の条件(1)~(8)でゲル・パーミエイション・クロマトグラフ(GPC)法により、重量平均分子量(Mw)と数平均分子量(Mn)を測定した。そして、測定したMw、Mnから重合体の分子量分布(Mw/Mn)を求めた。
(1)装置:東ソー(株)製HLC-8020
(2)分離カラム:東ソー(株)製GMH-XL(2本直列)
(3)測定温度:40℃
(4)キャリア:テトラヒドロフラン
(5)流量:0.6mL/分
(6)注入量:5μL
(7)検出器:示差屈折
(8)分子量標準:標準ポリスチレン
シート状の加硫ゴム組成物から幅1mmまたは2mm、長さ40mmの短冊状試験片を打ち抜き、試験に供した。(株)上島製作所製スペクトロメーターを用いて、動的歪振幅1%、周波数10Hz、温度50℃でtanδを測定した。tanδの逆数の値について基準比較例を100として指数表示した。数値が大きいほど転がり抵抗が小さく、低燃費性であることを示している。
転がり抵抗試験機を用い、試験用タイヤを、リム(15×6JJ)、内圧(230kPa)、荷重(3.43kN)、速度(80km/h)で走行させたときの転がり抵抗を測定し、基準比較例を100とした時の指数で表示した。指数は大きい方が良好(低燃費性)である。
各試験用タイヤを車両(国産FF2000cc)の全輪に装着して、湿潤アスファルト路面にて初速度100km/hからの制動距離を求めた。結果は指数で表し、数字が大きいほどウェットスキッド性能(ウェットグリップ性能)が良好である。指数は次の式で求めた。
ウェットスキッド性能=(基準比較例の制動距離)/(各実施例又は各比較例の制動距離)×100
LAT試験機(Laboratory Abrasion and Skid Tester)を用い、荷重50N、速度20km/h、スリップアングル5°の条件にて、各加硫ゴム組成物の容積損失量を測定した。表2及び3の数値(LAT指数)は、基準比較例の容積損失量を100としたときの相対値である。当該数値が大きいほど耐摩耗性に優れている。
内容積20リットルのステンレス製重合反応器内を洗浄、乾燥し、乾燥窒素で置換し、ヘキサン(比重0.68g/cm3)10.2kg、1,3-ブタジエン547g、スチレン173g、テトラヒドロフラン6.1ml、エチレングリコールジエチルエーテル5.0mlを重合反応容器内に投入した。次に、ビス(ジエチルアミノ)メチルビニルシラン16.0mmol及びn-ブチルリチウム18.5mmolを、それぞれ、シクロヘキサン溶液及びn-ヘキサン溶液として投入し、重合を開始した。
撹拌速度を130rpm、重合反応器内温度を65℃とし、単量体を重合反応容器内に連続的に供給しながら、1,3-ブタジエンとスチレンの共重合を3時間行った。全重合での1,3-ブタジエンの供給量は821g、スチレンの供給量は259gであった。
次に、得られた重合体溶液を130rpmの撹拌速度で撹拌し、1,3,5-トリス(3-トリメトキシシリルプロピル)イソシアヌレート4.0mmolを添加し、15分間撹拌した。重合体溶液にメタノール0.80mlを含むヘキサン溶液20mlを加えて、更に重合体溶液を5分間撹拌した。
内容積20リットルのステンレス製重合反応器内を洗浄、乾燥し、乾燥窒素で置換し、ヘキサン(比重0.68g/cm3)10.2kg、1,3-ブタジエン547g、スチレン173g、テトラヒドロフラン6.1ml、エチレングリコールジエチルエーテル5.0mlを重合反応容器内に投入した。次に、n-ブチルリチウム17.3mmolをn-ヘキサン溶液として投入し、1,3-ブタジエンとスチレンの共重合を1時間行った。重合中、撹拌速度を130rpm、重合反応器内温度を65℃とし、単量体を重合反応容器内に連続的に供給した。
該1時間の重合後、ビス(ジエチルアミノ)メチルビニルシラン14.4mmolをシクロヘキサン溶液として、撹拌速度を130rpm、重合反応器内温度を65℃の条件下で、重合反応器内に投入した。
次に、重合反応器内に連続的に単量体を供給し、1,3-ブタジエンとスチレンの共重合を0.5時間行った。重合中、撹拌速度を130rpm、重合反応器内温度を65℃とした。
該0.5時間の重合後、ビス(ジエチルアミノ)メチルビニルシラン14.4mmolをシクロヘキサン溶液として、撹拌速度を130rpm、重合反応器内温度を65℃の条件下で、重合反応器内に投入した。
次に、重合反応器内に連続的に単量体を供給し、1,3-ブタジエンとスチレンの共重合を0.5時間行った。重合中、撹拌速度を130rpm、重合反応器内温度を65℃とした。
該0.5時間の重合後、ビス(ジエチルアミノ)メチルビニルシラン14.4mmolをシクロヘキサン溶液として、撹拌速度を130rpm、重合反応器内温度を65℃の条件下で、重合反応器内に投入した。
次に、重合反応器内に連続的に単量体を供給し、1,3-ブタジエンとスチレンの共重合を0.5時間行った。重合中、撹拌速度を130rpm、重合反応器内温度を65℃とした。全重合での1,3-ブタジエンの供給量は821g、スチレンの供給量は259gであった。
次に、得られた重合体溶液を130rpmの撹拌速度で撹拌し、1,3,5-トリス(3-トリメトキシシリルプロピル)イソシアヌレート3.6mmolを添加し、15分間撹拌した。重合体溶液にメタノール0.80mlを含むヘキサン溶液20mlを加えて、更に重合体溶液を5分間撹拌した。
内容積5リットルのステンレス製重合反応器内を洗浄、乾燥し、乾燥窒素で置換し、ヘキサン(比重0.68g/cm3)2.55kg、1,3-ブタジエン137g、スチレン43g、テトラヒドロフラン1.5ml、エチレングリコールジエチルエーテル1.2mlを重合反応容器内に投入した。次に、n-ブチルリチウム3.6mmolをn-ヘキサン溶液として投入し、1,3-ブタジエンとスチレンの共重合を2.5時間行った。重合中、撹拌速度を130rpm、重合反応器内温度を65℃とし、単量体を重合反応容器内に連続的に供給した。1,3-ブタジエンの供給量は205g、スチレンの供給量は65gであった。
該2.5時間の重合後、ビス(ジエチルアミノ)メチルビニルシラン2.8mmolをシクロヘキサン溶液として、撹拌速度130rpm、重合反応器内温度を65℃の条件下で、重合反応器内に投入し30分間撹拌した。
次に、メタノール0.14mlを含むヘキサン溶液20mlを重合反応器内に投入し、重合体溶液を5分間撹拌した。
内容積20リットルのステンレス製重合反応器内を洗浄、乾燥し、乾燥窒素で置換し、ヘキサン(比重0.68g/cm3)10.2kg、1,3-ブタジエン547g、スチレン173g、テトラヒドロフラン6.1ml、エチレングリコールジエチルエーテル5.0mlを重合反応容器内に投入した。次に、ビス(ジエチルアミノ)メチルビニルシラン16.0mmol及びn-ブチルリチウム18.5mmolを、それぞれ、シクロヘキサン溶液及びn-ヘキサン溶液として投入し、重合を開始した。
撹拌速度を130rpm、重合反応器内温度を65℃とし、単量体を重合反応容器内に連続的に供給しながら、1,3-ブタジエンとスチレンの共重合を3時間行った。全重合での1,3-ブタジエンの供給量は821g、スチレンの供給量は259gであった。
次に、重合体溶液にメタノール0.80mlを含むヘキサン溶液20mlを加えて、更に重合体溶液を5分間撹拌した。
内容積20リットルのステンレス製重合反応器内を洗浄、乾燥し、乾燥窒素で置換し、ヘキサン(比重0.68g/cm3)10.2kg、1,3-ブタジエン547g、スチレン173g、テトラヒドロフラン6.1ml、エチレングリコールジエチルエーテル5.0mlを重合反応容器内に投入した。次に、n-ブチルリチウム18.5mmolをn-ヘキサン溶液として投入し、重合を開始した。
撹拌速度を130rpm、重合反応器内温度を65℃とし、単量体を重合反応容器内に連続的に供給しながら、1,3-ブタジエンとスチレンの共重合を3時間行った。全重合での1,3-ブタジエンの供給量は821g、スチレンの供給量は259gであった。
次に、得られた重合体溶液を130rpmの撹拌速度で撹拌し、1,3,5-トリス(3-トリメトキシシリルプロピル)イソシアヌレート4.0mmolを添加し、15分間撹拌した。重合体溶液にメタノール0.80mlを含むヘキサン溶液20mlを加えて、更に重合体溶液を5分間撹拌した。
内容積20リットルのステンレス製重合反応器内を洗浄、乾燥し、乾燥窒素で置換し、ヘキサン(比重0.68g/cm3)10.2kg、1,3-ブタジエン547g、スチレン173g、テトラヒドロフラン6.1ml、エチレングリコールジエチルエーテル5.0mlを重合反応容器内に投入した。次に、n-ブチルリチウム18.5mmolをn-ヘキサン溶液として投入し、重合を開始した。
撹拌速度を130rpm、重合反応器内温度を65℃とし、単量体を重合反応容器内に連続的に供給しながら、1,3-ブタジエンとスチレンの共重合を3時間行った。全重合での1,3-ブタジエンの供給量は821g、スチレンの供給量は259gであった。
次に、重合体溶液にメタノール0.80mlを含むヘキサン溶液20mlを加えて、更に重合体溶液を5分間撹拌した。
内容積20リットルのステンレス製重合反応器内を洗浄、乾燥し、乾燥窒素で置換し、ヘキサン(比重0.68g/cm3)10.2kg、1,3-ブタジエン547g、スチレン173g、テトラヒドロフラン6.1ml、エチレングリコールジエチルエーテル5.0mlを重合反応容器内に投入した。次に、ビス(ジエチルアミノ)メチルビニルシラン16.0mmol及びn-ブチルリチウム18.5mmolを、それぞれ、シクロヘキサン溶液及びn-ヘキサン溶液として投入し、重合を開始した。
撹拌速度を130rpm、重合反応器内温度を65℃とし、単量体を重合反応容器内に連続的に供給しながら、1,3-ブタジエンとスチレンの共重合を3時間行った。全重合での1,3-ブタジエンの供給量は821g、スチレンの供給量は259gであった。
次に、得られた重合体溶液を130rpmの撹拌速度で撹拌し、1,3,5-トリス(3-トリメトキシシリルプロピル)イソシアヌレート4.0mmolを添加し、15分間撹拌した。重合体溶液にメタノール0.80mlを含むヘキサン溶液20mlを加えて、更に重合体溶液を5分間撹拌した。
内容積20リットルのステンレス製重合反応器内を洗浄、乾燥し、乾燥窒素で置換し、ヘキサン(比重0.68g/cm3)10.2kg、1,3-ブタジエン547g、スチレン173g、テトラヒドロフラン6.1ml、エチレングリコールジエチルエーテル5.0mlを重合反応容器内に投入した。次に、ビス(ジエチルアミノ)メチルビニルシラン16.0mmol及びn-ブチルリチウム18.5mmolを、それぞれ、シクロヘキサン溶液及びn-ヘキサン溶液として投入し、重合を開始した。
撹拌速度を130rpm、重合反応器内温度を65℃とし、単量体を重合反応容器内に連続的に供給しながら、1,3-ブタジエンとスチレンの共重合を3時間行った。全重合での1,3-ブタジエンの供給量は821g、スチレンの供給量は259gであった。
次に、得られた重合体溶液を130rpmの撹拌速度で撹拌し、3-(メトキシ)プロピルトリメトキシシラン4.0mmolを添加し、15分間撹拌した。重合体溶液にメタノール0.80mlを含むヘキサン溶液20mlを加えて、更に重合体溶液を5分間撹拌した。
天然ゴム:RSS#3
ブタジエンゴム:宇部興産(株)製のウベポールBR150B
重合体1~8:上記製造例1~8
シリカ:デグッサ社製のウルトラシルVN3-G(N2SA:175m2/g)
シランカップリング剤:デグッサ社製のSi69(ビス(3-トリエトキシシリルプロピル)テトラスルフィド)
カーボンブラック:三菱化学(株)製のダイアブラックN339(N2SA:96m2/g、DBP吸収量:124ml/100g)
オイル:(株)ジャパンエナジー製のX-140
老化防止剤:住友化学(株)製のアンチゲン3C
ステアリン酸:日油(株)製のビーズステアリン酸つばき
酸化亜鉛:三井金属鉱業(株)製の亜鉛華1号
ワックス:大内新興化学工業(株)製のサンノックN
硫黄:鶴見化学工業(株)製の粉末硫黄
加硫促進剤1:住友化学(株)製のソクシノールCZ
加硫促進剤2:住友化学(株)製のソクシノールD
表2及び3に示す配合内容に従い、(株)神戸製鋼所製の1.7Lバンバリーミキサーを用いて、硫黄及び加硫促進剤以外の材料を150℃の条件下で5分間混練りし、混練り物を得た。次に、得られた混練り物に硫黄及び加硫促進剤を添加し、オープンロールを用いて、80℃の条件下で5分間練り込み、未加硫ゴム組成物を得た。得られた未加硫ゴム組成物を170℃で20分間、0.5mm厚の金型でプレス加硫し、加硫ゴム組成物を得た。
また、得られた未加硫ゴム組成物をトレッドの形状に成形し、タイヤ成型機上で他のタイヤ部材とともに貼り合わせて未加硫タイヤを形成し、170℃で12分間加硫し、試験用タイヤ(サイズ:195/65R15)を製造した。
Claims (10)
- ゴム成分及びシリカを含有し、
前記ゴム成分100質量%のうち、共役ジエンに基づく構成単位と下式(I)で表される構成単位とを有する共役ジエン系重合体であって、下式(II)で表される基及び/又は下式(III)で表される基を有するケイ素化合物によって重合体の少なくとも一端が変性されてなる共役ジエン系重合体の含有量が5質量%以上であり、
前記ゴム成分100質量部に対する前記シリカの含有量が5~150質量部であることを特徴とするゴム組成物。
- 式(Ia)のR1及びR2が炭素原子数1~6のヒドロカルビル基であることを特徴とする請求項1に記載のゴム組成物。
- 式(I)のX1、X2及びX3の2つが式(Ia)で表される基又は水酸基であることを特徴とする請求項1又は2に記載のゴム組成物。
- 共役ジエン系重合体のビニル結合量が、共役ジエンに基づく構成単位の含有量を100モル%として、10モル%以上80モル%以下であることを特徴とする請求項1~5のいずれかに記載のゴム組成物。
- 天然ゴム及び/又はブタジエンゴムを含有することを特徴とする請求項1~6のいずれかに記載のゴム組成物。
- 前記シリカの窒素吸着比表面積が40~400m2/gであることを特徴とする請求項1~7のいずれかに記載のゴム組成物。
- トレッド用ゴム組成物として用いられることを特徴とする請求項1~8のいずれかに記載のゴム組成物。
- 請求項1~9のいずれかに記載のゴム組成物を用いて作製した空気入りタイヤ。
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201180035191.XA CN103003346B (zh) | 2010-07-23 | 2011-07-22 | 橡胶组合物和充气轮胎 |
US13/700,382 US20130085225A1 (en) | 2010-07-23 | 2011-07-22 | Rubber composition and pneumatic tire |
EP11809741.9A EP2597116B1 (en) | 2010-07-23 | 2011-07-22 | Rubber composition and pneumatic tire |
BR112012031641A BR112012031641A2 (pt) | 2010-07-23 | 2011-07-22 | composição de borracha e pneu pneumático |
JP2012525447A JP5715628B2 (ja) | 2010-07-23 | 2011-07-22 | ゴム組成物及び空気入りタイヤ |
KR1020137000657A KR20130093587A (ko) | 2010-07-23 | 2011-07-22 | 고무 조성물 및 공기 타이어 |
RU2012156033/05A RU2573870C2 (ru) | 2010-07-23 | 2011-07-22 | Резиновая смесь и пневматическая шина |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2010-166248 | 2010-07-23 | ||
JP2010166248 | 2010-07-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2012011571A1 true WO2012011571A1 (ja) | 2012-01-26 |
Family
ID=45496988
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2011/066705 WO2012011571A1 (ja) | 2010-07-23 | 2011-07-22 | ゴム組成物及び空気入りタイヤ |
Country Status (8)
Country | Link |
---|---|
US (1) | US20130085225A1 (ja) |
EP (1) | EP2597116B1 (ja) |
JP (1) | JP5715628B2 (ja) |
KR (1) | KR20130093587A (ja) |
CN (1) | CN103003346B (ja) |
BR (1) | BR112012031641A2 (ja) |
RU (1) | RU2573870C2 (ja) |
WO (1) | WO2012011571A1 (ja) |
Cited By (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012131891A (ja) * | 2010-12-21 | 2012-07-12 | Sumitomo Rubber Ind Ltd | ゴム組成物及びスタッドレスタイヤ |
JP2012201699A (ja) * | 2011-03-23 | 2012-10-22 | Sumitomo Rubber Ind Ltd | ゴム組成物及び空気入りタイヤ |
JP2012255076A (ja) * | 2011-06-08 | 2012-12-27 | Sumitomo Rubber Ind Ltd | ゴム組成物及び空気入りタイヤ |
JP2012255074A (ja) * | 2011-06-08 | 2012-12-27 | Sumitomo Rubber Ind Ltd | ゴム組成物及び空気入りタイヤ |
JP2012255075A (ja) * | 2011-06-08 | 2012-12-27 | Sumitomo Rubber Ind Ltd | ゴム組成物及び空気入りタイヤ |
JP2013006902A (ja) * | 2011-06-22 | 2013-01-10 | Sumitomo Rubber Ind Ltd | ゴム組成物及び空気入りタイヤ |
JP2013006904A (ja) * | 2011-06-22 | 2013-01-10 | Sumitomo Rubber Ind Ltd | ゴム組成物及びそれを用いて作製した空気入りタイヤ |
WO2013077017A1 (ja) * | 2011-11-24 | 2013-05-30 | 住友ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
WO2013077020A1 (ja) * | 2011-11-24 | 2013-05-30 | 住友ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
WO2013077015A1 (ja) * | 2011-11-24 | 2013-05-30 | 住友ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
WO2013077016A1 (ja) * | 2011-11-24 | 2013-05-30 | 住友ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
WO2013077021A1 (ja) * | 2011-11-24 | 2013-05-30 | 住友ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
WO2013077019A1 (ja) * | 2011-11-24 | 2013-05-30 | 住友ゴム工業株式会社 | ゴム組成物及びスタッドレスタイヤ |
WO2013077018A1 (ja) * | 2011-11-24 | 2013-05-30 | 住友ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
WO2013099325A1 (ja) * | 2011-12-26 | 2013-07-04 | 住友ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
WO2013099324A1 (ja) * | 2011-12-26 | 2013-07-04 | 住友ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
JP2013203903A (ja) * | 2012-03-28 | 2013-10-07 | Sumitomo Rubber Ind Ltd | トラック・バスタイヤ用ゴム組成物及びトラック・バスタイヤ |
JP2013221102A (ja) * | 2012-04-17 | 2013-10-28 | Sumitomo Rubber Ind Ltd | スタッドレスタイヤ用ゴム組成物及びスタッドレスタイヤ |
JP2013221101A (ja) * | 2012-04-17 | 2013-10-28 | Sumitomo Rubber Ind Ltd | サイドウォール用ゴム組成物及び空気入りタイヤ |
JP2013241527A (ja) * | 2012-05-21 | 2013-12-05 | Sumitomo Rubber Ind Ltd | サイドウォール用ゴム組成物及び空気入りタイヤ |
JP2013245263A (ja) * | 2012-05-24 | 2013-12-09 | Sumitomo Rubber Ind Ltd | サイドウォール用ゴム組成物及び空気入りタイヤ |
JP2013249423A (ja) * | 2012-06-01 | 2013-12-12 | Sumitomo Rubber Ind Ltd | スタッドレスタイヤ用ゴム組成物及びスタッドレスタイヤ |
JP2013249420A (ja) * | 2012-06-01 | 2013-12-12 | Sumitomo Rubber Ind Ltd | スタッドレスタイヤ用ゴム組成物及びスタッドレスタイヤ |
JP2013249422A (ja) * | 2012-06-01 | 2013-12-12 | Sumitomo Rubber Ind Ltd | トラック・バスタイヤ用ゴム組成物及びトラック・バスタイヤ |
JP2013253207A (ja) * | 2012-06-08 | 2013-12-19 | Sumitomo Rubber Ind Ltd | トラック・バスタイヤ用ゴム組成物及びトラック・バスタイヤ |
JP2014001303A (ja) * | 2012-06-18 | 2014-01-09 | Sumitomo Rubber Ind Ltd | サイドウォール用ゴム組成物及び空気入りタイヤ |
US9284433B2 (en) | 2011-08-03 | 2016-03-15 | Sumitomo Rubber Industries, Ltd. | Rubber composition and pneumatic tire |
KR20170074677A (ko) * | 2015-12-22 | 2017-06-30 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이의 제조방법 |
JP2019048925A (ja) * | 2017-09-08 | 2019-03-28 | 横浜ゴム株式会社 | ゴム組成物及び空気入りタイヤ |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6181529B2 (ja) * | 2013-11-25 | 2017-08-16 | 住友ゴム工業株式会社 | 空気入りタイヤ |
US11124590B2 (en) * | 2016-11-02 | 2021-09-21 | Public Joint Stock Company “SIBUR Holding” | Method of producing a modified diene-containing rubber, the rubber and a composition based thereon |
JP7403297B2 (ja) * | 2019-12-10 | 2023-12-22 | 株式会社ブリヂストン | 組成物及びポリマー成形体 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000344955A (ja) | 1999-06-04 | 2000-12-12 | Sumitomo Rubber Ind Ltd | 変性ジエン系ゴム組成物 |
JP2010077416A (ja) * | 2008-08-27 | 2010-04-08 | Sumitomo Chemical Co Ltd | 共役ジエン系重合体及び共役ジエン系重合体組成物 |
JP2010077412A (ja) * | 2008-08-27 | 2010-04-08 | Sumitomo Chemical Co Ltd | 共役ジエン系重合体、共役ジエン系重合体組成物及び共役ジエン系重合体の製造方法 |
JP2010077414A (ja) * | 2008-08-27 | 2010-04-08 | Sumitomo Chemical Co Ltd | 共役ジエン系重合体、共役ジエン系重合体組成物及び共役ジエン系重合体の製造方法 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3937681A (en) * | 1969-02-07 | 1976-02-10 | Chemische Werke Huels Aktiengesellschaft | Tire tread of homopolymers of butadiene |
US4836262A (en) * | 1986-08-08 | 1989-06-06 | Bridgestone Corporation | Metal cords and pneumatic tires using the same |
BR9916543B1 (pt) * | 1998-12-22 | 2008-11-18 | processo para a produÇço de pneus para as rodas de veÍculos, composiÇço compreendendo um polÍmero elastomÉrico, processo para a preparaÇço de uma composiÇço elastomÉrica, produto reticulado manufaturado, e, pneu para rodas de veÍculos. | |
US20020011293A1 (en) * | 1999-03-02 | 2002-01-31 | David John Zanzig | Tire with reinforced rubber sidewall |
US20050272852A1 (en) * | 2004-06-02 | 2005-12-08 | Sandstrom Paul H | Natural rubber-rich composition and tire with tread thereof |
US7625981B2 (en) * | 2004-06-04 | 2009-12-01 | Sumitomo Chemical Company, Limited | Process for producing modified polymer rubber |
EP1932869B1 (en) * | 2005-10-05 | 2013-12-11 | JSR Corporation | Process for producing modified conjugated diene polymer, modified conjugated diene polymer obtained by the process, and rubber composition containing the same |
JP5745733B2 (ja) * | 2006-10-25 | 2015-07-08 | Jsr株式会社 | 変性重合体の製造方法、その方法により得られた変性重合体とそのゴム組成物 |
JP5756248B2 (ja) * | 2008-04-28 | 2015-07-29 | 株式会社ブリヂストン | タイヤ |
TW201022301A (en) * | 2008-08-27 | 2010-06-16 | Sumitomo Chemical Co | Conjugated diene polymer, conjugated diene polymer composition, and method for producing conjugated diene polymer |
SG159479A1 (en) * | 2008-08-27 | 2010-03-30 | Sumitomo Chemical Co | Conjugated diene polymer, conjugated diene polymer composition, and method for producing conjugated diene polymer |
CN101724184B (zh) * | 2008-10-29 | 2013-05-01 | 住友橡胶工业株式会社 | 橡胶组合物及轮胎 |
WO2012011570A1 (ja) * | 2010-07-23 | 2012-01-26 | 住友ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
-
2011
- 2011-07-22 CN CN201180035191.XA patent/CN103003346B/zh not_active Expired - Fee Related
- 2011-07-22 RU RU2012156033/05A patent/RU2573870C2/ru not_active IP Right Cessation
- 2011-07-22 EP EP11809741.9A patent/EP2597116B1/en not_active Not-in-force
- 2011-07-22 JP JP2012525447A patent/JP5715628B2/ja active Active
- 2011-07-22 WO PCT/JP2011/066705 patent/WO2012011571A1/ja active Application Filing
- 2011-07-22 BR BR112012031641A patent/BR112012031641A2/pt not_active IP Right Cessation
- 2011-07-22 US US13/700,382 patent/US20130085225A1/en not_active Abandoned
- 2011-07-22 KR KR1020137000657A patent/KR20130093587A/ko not_active Application Discontinuation
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000344955A (ja) | 1999-06-04 | 2000-12-12 | Sumitomo Rubber Ind Ltd | 変性ジエン系ゴム組成物 |
JP2010077416A (ja) * | 2008-08-27 | 2010-04-08 | Sumitomo Chemical Co Ltd | 共役ジエン系重合体及び共役ジエン系重合体組成物 |
JP2010077412A (ja) * | 2008-08-27 | 2010-04-08 | Sumitomo Chemical Co Ltd | 共役ジエン系重合体、共役ジエン系重合体組成物及び共役ジエン系重合体の製造方法 |
JP2010077414A (ja) * | 2008-08-27 | 2010-04-08 | Sumitomo Chemical Co Ltd | 共役ジエン系重合体、共役ジエン系重合体組成物及び共役ジエン系重合体の製造方法 |
Non-Patent Citations (1)
Title |
---|
See also references of EP2597116A4 |
Cited By (40)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012131891A (ja) * | 2010-12-21 | 2012-07-12 | Sumitomo Rubber Ind Ltd | ゴム組成物及びスタッドレスタイヤ |
JP2012201699A (ja) * | 2011-03-23 | 2012-10-22 | Sumitomo Rubber Ind Ltd | ゴム組成物及び空気入りタイヤ |
JP2012255076A (ja) * | 2011-06-08 | 2012-12-27 | Sumitomo Rubber Ind Ltd | ゴム組成物及び空気入りタイヤ |
JP2012255074A (ja) * | 2011-06-08 | 2012-12-27 | Sumitomo Rubber Ind Ltd | ゴム組成物及び空気入りタイヤ |
JP2012255075A (ja) * | 2011-06-08 | 2012-12-27 | Sumitomo Rubber Ind Ltd | ゴム組成物及び空気入りタイヤ |
JP2013006902A (ja) * | 2011-06-22 | 2013-01-10 | Sumitomo Rubber Ind Ltd | ゴム組成物及び空気入りタイヤ |
JP2013006904A (ja) * | 2011-06-22 | 2013-01-10 | Sumitomo Rubber Ind Ltd | ゴム組成物及びそれを用いて作製した空気入りタイヤ |
US9284433B2 (en) | 2011-08-03 | 2016-03-15 | Sumitomo Rubber Industries, Ltd. | Rubber composition and pneumatic tire |
WO2013077016A1 (ja) * | 2011-11-24 | 2013-05-30 | 住友ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
WO2013077015A1 (ja) * | 2011-11-24 | 2013-05-30 | 住友ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
US9006326B2 (en) | 2011-11-24 | 2015-04-14 | Sumitomo Rubber Industries, Ltd. | Rubber composition and pneumatic tire |
WO2013077021A1 (ja) * | 2011-11-24 | 2013-05-30 | 住友ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
WO2013077019A1 (ja) * | 2011-11-24 | 2013-05-30 | 住友ゴム工業株式会社 | ゴム組成物及びスタッドレスタイヤ |
WO2013077018A1 (ja) * | 2011-11-24 | 2013-05-30 | 住友ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
US9428641B2 (en) | 2011-11-24 | 2016-08-30 | Sumitomo Rubber Industries, Ltd. | Rubber composition, and pneumatic tire |
US9290644B2 (en) | 2011-11-24 | 2016-03-22 | Sumitomo Rubber Industries, Ltd. | Rubber composition, and pneumatic tire |
WO2013077020A1 (ja) * | 2011-11-24 | 2013-05-30 | 住友ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
WO2013077017A1 (ja) * | 2011-11-24 | 2013-05-30 | 住友ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
US9221964B2 (en) | 2011-11-24 | 2015-12-29 | Sumitomo Rubber Industries, Ltd. | Rubber composition and pneumatic tire |
US9120890B2 (en) | 2011-11-24 | 2015-09-01 | Sumitomo Rubber Industries, Ltd. | Rubber composition and pneumatic tire |
US9284438B2 (en) | 2011-12-26 | 2016-03-15 | Sumitomo Rubber Industries, Ltd. | Rubber composition and pneumatic tire |
WO2013099325A1 (ja) * | 2011-12-26 | 2013-07-04 | 住友ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
US9359491B2 (en) | 2011-12-26 | 2016-06-07 | Sumitomo Rubber Industries, Ltd. | Rubber composition and pneumatic tire |
WO2013099324A1 (ja) * | 2011-12-26 | 2013-07-04 | 住友ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
JP2013203903A (ja) * | 2012-03-28 | 2013-10-07 | Sumitomo Rubber Ind Ltd | トラック・バスタイヤ用ゴム組成物及びトラック・バスタイヤ |
JP2013221102A (ja) * | 2012-04-17 | 2013-10-28 | Sumitomo Rubber Ind Ltd | スタッドレスタイヤ用ゴム組成物及びスタッドレスタイヤ |
JP2013221101A (ja) * | 2012-04-17 | 2013-10-28 | Sumitomo Rubber Ind Ltd | サイドウォール用ゴム組成物及び空気入りタイヤ |
JP2013241527A (ja) * | 2012-05-21 | 2013-12-05 | Sumitomo Rubber Ind Ltd | サイドウォール用ゴム組成物及び空気入りタイヤ |
JP2013245263A (ja) * | 2012-05-24 | 2013-12-09 | Sumitomo Rubber Ind Ltd | サイドウォール用ゴム組成物及び空気入りタイヤ |
JP2013249422A (ja) * | 2012-06-01 | 2013-12-12 | Sumitomo Rubber Ind Ltd | トラック・バスタイヤ用ゴム組成物及びトラック・バスタイヤ |
JP2013249423A (ja) * | 2012-06-01 | 2013-12-12 | Sumitomo Rubber Ind Ltd | スタッドレスタイヤ用ゴム組成物及びスタッドレスタイヤ |
JP2013249420A (ja) * | 2012-06-01 | 2013-12-12 | Sumitomo Rubber Ind Ltd | スタッドレスタイヤ用ゴム組成物及びスタッドレスタイヤ |
JP2013253207A (ja) * | 2012-06-08 | 2013-12-19 | Sumitomo Rubber Ind Ltd | トラック・バスタイヤ用ゴム組成物及びトラック・バスタイヤ |
JP2014001303A (ja) * | 2012-06-18 | 2014-01-09 | Sumitomo Rubber Ind Ltd | サイドウォール用ゴム組成物及び空気入りタイヤ |
KR20170074677A (ko) * | 2015-12-22 | 2017-06-30 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이의 제조방법 |
JP2018530526A (ja) * | 2015-12-22 | 2018-10-18 | エルジー・ケム・リミテッド | 変性共役ジエン系重合体およびその製造方法 |
KR102021844B1 (ko) * | 2015-12-22 | 2019-09-17 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이의 제조방법 |
US10604591B2 (en) | 2015-12-22 | 2020-03-31 | Lg Chem, Ltd. | Modified and conjugated diene-based polymer and method for preparing thereof |
JP2019048925A (ja) * | 2017-09-08 | 2019-03-28 | 横浜ゴム株式会社 | ゴム組成物及び空気入りタイヤ |
JP7027739B2 (ja) | 2017-09-08 | 2022-03-02 | 横浜ゴム株式会社 | ゴム組成物及び空気入りタイヤ |
Also Published As
Publication number | Publication date |
---|---|
BR112012031641A2 (pt) | 2016-11-08 |
EP2597116A4 (en) | 2014-07-02 |
EP2597116A1 (en) | 2013-05-29 |
RU2573870C2 (ru) | 2016-01-27 |
JPWO2012011571A1 (ja) | 2013-09-09 |
RU2012156033A (ru) | 2014-08-27 |
CN103003346A (zh) | 2013-03-27 |
CN103003346B (zh) | 2015-12-02 |
EP2597116B1 (en) | 2015-09-09 |
US20130085225A1 (en) | 2013-04-04 |
KR20130093587A (ko) | 2013-08-22 |
JP5715628B2 (ja) | 2015-05-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5715628B2 (ja) | ゴム組成物及び空気入りタイヤ | |
JP5767639B2 (ja) | ゴム組成物及び空気入りタイヤ | |
JP5632917B2 (ja) | ゴム組成物及び空気入りタイヤ | |
JP5762412B2 (ja) | ゴム組成物及び空気入りタイヤ | |
JP5623986B2 (ja) | ゴム組成物及び空気入りタイヤ | |
JP5623972B2 (ja) | ゴム組成物及び空気入りタイヤ | |
WO2012011569A1 (ja) | ゴム組成物及び空気入りタイヤ | |
JP5628750B2 (ja) | ゴム組成物及び空気入りタイヤ | |
JP5628759B2 (ja) | ゴム組成物及び空気入りタイヤ | |
JP2012229385A (ja) | ゴム組成物及び空気入りタイヤ | |
JP2012233069A (ja) | ゴム組成物及び空気入りタイヤ | |
JP2013107989A (ja) | ゴム組成物及び空気入りタイヤ | |
JP5628751B2 (ja) | ゴム組成物及び空気入りタイヤ | |
JP5623946B2 (ja) | ゴム組成物及び空気入りタイヤ | |
JP2012255075A (ja) | ゴム組成物及び空気入りタイヤ | |
JP2013006904A (ja) | ゴム組成物及びそれを用いて作製した空気入りタイヤ | |
JP5628743B2 (ja) | ゴム組成物及び空気入りタイヤ | |
JP2013018812A (ja) | ゴム組成物及び空気入りタイヤ | |
JP2013100425A (ja) | ゴム組成物及び空気入りタイヤ | |
JP2013091735A (ja) | ゴム組成物及び空気入りタイヤ | |
JP2012233094A (ja) | ゴム組成物及び空気入りタイヤ | |
JP2013006902A (ja) | ゴム組成物及び空気入りタイヤ | |
JP2012246476A (ja) | ゴム組成物及び空気入りタイヤ | |
JP2013091736A (ja) | ゴム組成物及び空気入りタイヤ | |
JP2013018811A (ja) | ゴム組成物及び空気入りタイヤ |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 201180035191.X Country of ref document: CN |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 11809741 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2012525447 Country of ref document: JP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 3655/KOLNP/2012 Country of ref document: IN |
|
WWE | Wipo information: entry into national phase |
Ref document number: 13700382 Country of ref document: US |
|
ENP | Entry into the national phase |
Ref document number: 20137000657 Country of ref document: KR Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2011809741 Country of ref document: EP |
|
ENP | Entry into the national phase |
Ref document number: 2012156033 Country of ref document: RU Kind code of ref document: A |
|
REG | Reference to national code |
Ref country code: BR Ref legal event code: B01A Ref document number: 112012031641 Country of ref document: BR |
|
ENP | Entry into the national phase |
Ref document number: 112012031641 Country of ref document: BR Kind code of ref document: A2 Effective date: 20121211 |