JPWO2008114756A1 - 共役ジオレフィン共重合ゴム、その製造方法、ゴム組成物およびタイヤ - Google Patents
共役ジオレフィン共重合ゴム、その製造方法、ゴム組成物およびタイヤ Download PDFInfo
- Publication number
- JPWO2008114756A1 JPWO2008114756A1 JP2009505210A JP2009505210A JPWO2008114756A1 JP WO2008114756 A1 JPWO2008114756 A1 JP WO2008114756A1 JP 2009505210 A JP2009505210 A JP 2009505210A JP 2009505210 A JP2009505210 A JP 2009505210A JP WO2008114756 A1 JPWO2008114756 A1 JP WO2008114756A1
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- Prior art keywords
- compound
- copolymer rubber
- conjugated diolefin
- rubber
- aromatic vinyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 229920001971 elastomer Polymers 0.000 title claims abstract description 279
- 239000005060 rubber Substances 0.000 title claims abstract description 279
- 229920001577 copolymer Polymers 0.000 title claims abstract description 234
- 239000000203 mixture Substances 0.000 title claims description 80
- 238000000034 method Methods 0.000 title claims description 42
- -1 aromatic vinyl compound Chemical class 0.000 claims abstract description 161
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 98
- 150000001993 dienes Chemical class 0.000 claims abstract description 46
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 34
- 125000005370 alkoxysilyl group Chemical group 0.000 claims abstract description 32
- 238000006116 polymerization reaction Methods 0.000 claims description 120
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 116
- 229920000642 polymer Polymers 0.000 claims description 95
- 150000001875 compounds Chemical class 0.000 claims description 62
- 239000000377 silicon dioxide Substances 0.000 claims description 60
- 238000006243 chemical reaction Methods 0.000 claims description 41
- 229910052757 nitrogen Inorganic materials 0.000 claims description 37
- 239000003999 initiator Substances 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 24
- 125000003277 amino group Chemical group 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 239000003921 oil Substances 0.000 claims description 20
- 239000000945 filler Substances 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 150000003112 potassium compounds Chemical class 0.000 claims description 18
- 229910052783 alkali metal Inorganic materials 0.000 claims description 16
- 150000001340 alkali metals Chemical class 0.000 claims description 16
- 230000009477 glass transition Effects 0.000 claims description 16
- 239000000178 monomer Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 claims description 12
- 239000004215 Carbon black (E152) Substances 0.000 claims description 11
- 229930195733 hydrocarbon Natural products 0.000 claims description 11
- 150000002430 hydrocarbons Chemical class 0.000 claims description 11
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- JRFVCFVEJBDLDT-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]-n,n-bis(trimethylsilyl)propan-1-amine Chemical compound CO[Si](C)(OC)CCCN([Si](C)(C)C)[Si](C)(C)C JRFVCFVEJBDLDT-UHFFFAOYSA-N 0.000 claims description 8
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 8
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 6
- 150000002894 organic compounds Chemical class 0.000 claims description 6
- 239000002879 Lewis base Substances 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 150000007527 lewis bases Chemical class 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 239000012429 reaction media Substances 0.000 claims description 5
- DIGKGWWSMMWBIZ-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]-n,n-bis(trimethylsilyl)propan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN([Si](C)(C)C)[Si](C)(C)C DIGKGWWSMMWBIZ-UHFFFAOYSA-N 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- 150000001341 alkaline earth metal compounds Chemical class 0.000 claims description 3
- 238000007334 copolymerization reaction Methods 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 23
- 239000000463 material Substances 0.000 abstract description 10
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 40
- 239000006229 carbon black Substances 0.000 description 30
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 28
- 230000000704 physical effect Effects 0.000 description 27
- 238000013329 compounding Methods 0.000 description 26
- 230000000052 comparative effect Effects 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 125000001302 tertiary amino group Chemical group 0.000 description 20
- 238000009472 formulation Methods 0.000 description 19
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- 238000011156 evaluation Methods 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 15
- 239000003505 polymerization initiator Substances 0.000 description 15
- 238000005096 rolling process Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 14
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 12
- 230000006872 improvement Effects 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- 238000004898 kneading Methods 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 10
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 10
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000000977 initiatory effect Effects 0.000 description 9
- 239000005048 methyldichlorosilane Substances 0.000 description 9
- 229920002545 silicone oil Polymers 0.000 description 9
- 239000012744 reinforcing agent Substances 0.000 description 8
- 238000002156 mixing Methods 0.000 description 7
- 229920003048 styrene butadiene rubber Polymers 0.000 description 7
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 235000010446 mineral oil Nutrition 0.000 description 5
- 150000003335 secondary amines Chemical class 0.000 description 5
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 229920003244 diene elastomer Polymers 0.000 description 4
- 230000009977 dual effect Effects 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 4
- 239000010734 process oil Substances 0.000 description 4
- 150000003606 tin compounds Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- 235000014692 zinc oxide Nutrition 0.000 description 4
- IPKOJSMGLIKFLO-UHFFFAOYSA-N 2,2,5,5-tetramethyl-1,2,5-azadisilolidine Chemical compound C[Si]1(C)CC[Si](C)(C)N1 IPKOJSMGLIKFLO-UHFFFAOYSA-N 0.000 description 3
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
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- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- 125000001979 organolithium group Chemical group 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
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- 239000011593 sulfur Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 3
- 238000004073 vulcanization Methods 0.000 description 3
- 239000004636 vulcanized rubber Substances 0.000 description 3
- AGJAUFUNZWHLKE-UHFFFAOYSA-N (2E,4E)-N-isobutyl-2,4-tetradecadienamide Natural products CCCCCCCCCC=CC=CC(=O)NCC(C)C AGJAUFUNZWHLKE-UHFFFAOYSA-N 0.000 description 2
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
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- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CLSYMLFZZWDOLE-UHFFFAOYSA-N C=CC1=CC=CC=C1.C(CCCCCCCCCCC)OS(=O)(=O)C1=CC=CC=C1.[K] Chemical compound C=CC1=CC=CC=C1.C(CCCCCCCCCCC)OS(=O)(=O)C1=CC=CC=C1.[K] CLSYMLFZZWDOLE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
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- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 238000005299 abrasion Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 230000003712 anti-aging effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- WTWBUQJHJGUZCY-UHFFFAOYSA-N cuminaldehyde Chemical compound CC(C)C1=CC=C(C=O)C=C1 WTWBUQJHJGUZCY-UHFFFAOYSA-N 0.000 description 2
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
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- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 150000002642 lithium compounds Chemical class 0.000 description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
- PDZGAEAUKGKKDE-UHFFFAOYSA-N lithium;naphthalene Chemical compound [Li].C1=CC=CC2=CC=CC=C21 PDZGAEAUKGKKDE-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- DRXHEPWCWBIQFJ-UHFFFAOYSA-N methyl(triphenoxy)silane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(C)OC1=CC=CC=C1 DRXHEPWCWBIQFJ-UHFFFAOYSA-N 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 2
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- JLSBBCYKZLAADL-UHFFFAOYSA-N n-benzylmethanimine Chemical compound C=NCC1=CC=CC=C1 JLSBBCYKZLAADL-UHFFFAOYSA-N 0.000 description 1
- OBYVIBDTOCAXSN-UHFFFAOYSA-N n-butan-2-ylbutan-2-amine Chemical compound CCC(C)NC(C)CC OBYVIBDTOCAXSN-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical class CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- IJJSYKQZFFGIEE-UHFFFAOYSA-N naphthalene;potassium Chemical compound [K].C1=CC=CC2=CC=CC=C21 IJJSYKQZFFGIEE-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- FABOKLHQXVRECE-UHFFFAOYSA-N phenyl(tripropoxy)silane Chemical compound CCCO[Si](OCCC)(OCCC)C1=CC=CC=C1 FABOKLHQXVRECE-UHFFFAOYSA-N 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- LDIPVKABLDWRGC-UHFFFAOYSA-N phenylmethoxymethylbenzene;potassium Chemical compound [K].C=1C=CC=CC=1COCC1=CC=CC=C1 LDIPVKABLDWRGC-UHFFFAOYSA-N 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 125000005543 phthalimide group Chemical class 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- HSJXWMZKBLUOLQ-UHFFFAOYSA-M potassium;2-dodecylbenzenesulfonate Chemical compound [K+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HSJXWMZKBLUOLQ-UHFFFAOYSA-M 0.000 description 1
- ZRLVQFQTCMUIRM-UHFFFAOYSA-N potassium;2-methylbutan-2-olate Chemical compound [K+].CCC(C)(C)[O-] ZRLVQFQTCMUIRM-UHFFFAOYSA-N 0.000 description 1
- WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical compound NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 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
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- ADLSSRLDGACTEX-UHFFFAOYSA-N tetraphenyl silicate Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 ADLSSRLDGACTEX-UHFFFAOYSA-N 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- RYFIHIMBHQWVNQ-UHFFFAOYSA-N tributoxy(chloro)silane Chemical compound CCCCO[Si](Cl)(OCCCC)OCCCC RYFIHIMBHQWVNQ-UHFFFAOYSA-N 0.000 description 1
- SGCFZHOZKKQIBU-UHFFFAOYSA-N tributoxy(ethenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C=C SGCFZHOZKKQIBU-UHFFFAOYSA-N 0.000 description 1
- GIHPVQDFBJMUAO-UHFFFAOYSA-N tributoxy(ethyl)silane Chemical compound CCCCO[Si](CC)(OCCCC)OCCCC GIHPVQDFBJMUAO-UHFFFAOYSA-N 0.000 description 1
- GYZQBXUDWTVJDF-UHFFFAOYSA-N tributoxy(methyl)silane Chemical compound CCCCO[Si](C)(OCCCC)OCCCC GYZQBXUDWTVJDF-UHFFFAOYSA-N 0.000 description 1
- INUOIYMEJLOQFN-UHFFFAOYSA-N tributoxy(phenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C1=CC=CC=C1 INUOIYMEJLOQFN-UHFFFAOYSA-N 0.000 description 1
- MTLNOUGNCGMFMH-UHFFFAOYSA-H trichloro(2-trichlorostannylethyl)stannane Chemical compound Cl[Sn](Cl)(Cl)CC[Sn](Cl)(Cl)Cl MTLNOUGNCGMFMH-UHFFFAOYSA-H 0.000 description 1
- BCMNMJSREMRSFP-UHFFFAOYSA-H trichloro(4-trichlorostannylbutyl)stannane Chemical compound Cl[Sn](Cl)(Cl)CCCC[Sn](Cl)(Cl)Cl BCMNMJSREMRSFP-UHFFFAOYSA-H 0.000 description 1
- BOEGBYDAWIJZGT-UHFFFAOYSA-N trichloromethyltin Chemical compound ClC(Cl)(Cl)[Sn] BOEGBYDAWIJZGT-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-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
- NKLYMYLJOXIVFB-UHFFFAOYSA-N triethoxymethylsilane Chemical compound CCOC([SiH3])(OCC)OCC NKLYMYLJOXIVFB-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ZYMHKOVQDOFPHH-UHFFFAOYSA-N trimethoxy(oct-1-enyl)silane Chemical compound CCCCCCC=C[Si](OC)(OC)OC ZYMHKOVQDOFPHH-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- IXJNGXCZSCHDFE-UHFFFAOYSA-N triphenoxy(phenyl)silane Chemical compound C=1C=CC=CC=1O[Si](C=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 IXJNGXCZSCHDFE-UHFFFAOYSA-N 0.000 description 1
- FPKMSRRUOFZBQR-UHFFFAOYSA-N triphenoxymethylsilane Chemical compound O(C1=CC=CC=C1)C(OC1=CC=CC=C1)(OC1=CC=CC=C1)[SiH3] FPKMSRRUOFZBQR-UHFFFAOYSA-N 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- B60—VEHICLES IN GENERAL
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- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
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- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/02—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type
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- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
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Abstract
Description
(1)共重合体鎖に結合した第1級アミノ基とアルコキシシリル基とを有しており、
(2)芳香族ビニル化合物の重合単位の含有量が共重合ゴムの5重量%以上60重量%以下であり、
(3)芳香族ビニル化合物が共重合ゴムの共重合体鎖の片方の端部に密に、他方の端部に粗に分布しており、かつ
(4)差動走査熱量計(DSC)によって分析される吸熱曲線におけるガラス転移温度域での変曲点間の温度差(△Tg)が25℃以上、
である、共役ジオレフィン共重合ゴム。
または下記式(2)
で表わされる、上記[1]〜[5]のいずれかに記載の共役ジオレフィン共重合ゴム。
または下記式(4)
で表わされる少なくとも1つのアミノ基含有アルコキシシラン化合物を反応させ、しかる後加水分解することにより、共役ジオレフィン共重合ゴムを製造する、上記[7]に記載の方法(以下、「第1製造法」という)。
(R4R5R6Si)2−N−R1−Li (5)
[ここで、R1の定義は上記式(1)に同じであり、R4,R5およびR6の定義は、上記式(3)に同じである]、
または、下記式(6)
で表わされるリチウムアミド開始剤を用いて、共役ジオレフィンと芳香族ビニル化合物をアニオン重合させるに際し、反応媒体中にカリウム化合物を添加するとともに、重合反応の開始時に芳香族ビニル化合物と共役ジオレフィンとのモル比が0.5以上の割合となるモノマー組成で重合反応を行い、
そのようにして得られた重合活性末端と、
下記式(7)
で表わされるアルコキシシラン化合物を反応させることにより、共役ジオレフィン共重合ゴムを製造する、上記[7]に記載の方法(以下、「第2製造法」という)。
または、次の式(2)
によって表わすことができる。そして、この式(1)または式(2)中の共重合体鎖のPが、上述のような芳香族ビニル化合物単位が共重合体鎖の中でその片方の端部に密に偏在している共役ジオレフィン芳香族ビニル化合物共重合体鎖である。
(R4R5R6Si)2−N−R1−Li (5)
[ここで、R1,R4,R5およびR6の定義は、上記式(3)に同じである]、
または、下記式(6)
で表されるアルコキシシラン化合物を添加してリビング重合鎖末端に反応せしめることにより製造することができる。
(R4R5R6Si)2−N−R1−X (8)
ここで、R1、R4、R5およびR6の定義は、上記式(3)に同じである、Xはハロゲン原子である、
または下記式(9)
を挙げることができる。
エポキシ基含有化合物:ブチルグリシジルエーテル、ジグリシジルエーテル、酸化プロピレン、ネオペンチルグリコールシグリシジルエーテル、エポキシ樹脂、エポキシ化大豆油、エポキシ化脂肪酸エステルなど。
カルボン酸化合物:アジピン酸、オクチル酸、メタクリル酸など。
カルボン酸エステル化合物:アクリル酸エステル、アクリル酸ジエチレン、メタクリル酸エチル、オルト酢酸エステル、アセト酢酸エチル、酢酸ブチル、酢酸イソプロピル、ジメチルカーボネート、p−ヒドロキシフェニル酢酸、ポリエステル系可塑剤、ステアリン酸系可塑剤など。
エーテル化合物:イソプロピルエーテル、ジブチルエーテルなど。
アルデヒド化合物:ウンデシレンアルデヒド、デシルアルデヒド、バニリン、3,4−ジメトキシベンズアルデヒド、クミンアルデヒドなど。
アミノ基含有化合物:イソプロピルアミン、ジイソプロピルアミン、トリエチルアミン、3−エトキシプロピルアミン、2−エチルヘキシルアミン、イソプロパノールアミン、N−エチルエチレンジアミン、エチレンイミン、ヘキサメチレンジアミン、3−ラウリルオキシプロピルアミン、アミノフェノール、アニリン、3−イソプロポキシアニリン、フェニレンジアミン、アミノピリジン、N−メチルジエタノールアミン、N−メチルエタノールアミン、3−アミノ−1−プロパノール、塩酸エチルアミン、塩酸−n−ブチルアミンなど。
アルコキシシラン化合物:トリメチルメトキシシラン、トリメチルエトキシシラン、ジメチルジメトキシシラン、メチルトリエトキシシラン、メチルトリフェノキシシラン、テトラエトキシシラン、メチルジエトキシシラン、ビニルトリメトキシシランなど。
シロキサン化合物:ジメチルシロキサンオリゴマー、シリコーンオイル、アミノ変性シリコーンオイル、エポキシ変性シリコーンオイル、カルボキシル変性シリコーンオイル、ポリエーテル変性シリコーンオイル、アルキル変性シリコーンオイル、高級脂肪酸エステル変性シリコーンオイル、高級アルコキシ変性シリコーンオイル、高級脂肪酸含有シリコーンオイルなど。
アミノシラン化合物:ヘキサメチルジシラザン、ノナメチルトリシラザン、アニリトリメチルシラン、ビス(ジメチルアミノ)ジメチルシラン、ビス(ジエチルアミノ)ジメチルシラン、トリエチルアミノシランなど。
(1)結合スチレン含量:
270MHz1H−NMRによって求めた。
(2)共役ジオレフィン部分のビニル含量:
270MHz1H−NMRによって求めた。
田中らの方法〔Polymer, 22, 1721(1981)〕にしたがって、スチレンブタジエン共重合
ゴムをオゾンによって分解した後、ゲルパーミエーションクロマトグラフィー(GPC)によって分析した。
ASTM D3418に従ってガラス転移点を測定した。測定されたガラス転移域でのTf(extrapolated onset temperature; ℃)とTe(extrapolated end temperature; ℃)の温度差をもって 「ガラス転移温度域での変曲点間の温度差」とした。
(5)ムーニー粘度(ML1+4、100℃):
JIS K6300-1に従って、Lローター、予熱1分、ローター作動時間4分、温
度100℃で求めた。
まず重合体をトルエンに溶解した後、大量のメタノール中で沈殿させることにより共重合ゴムに結合していないアミノ基含有化合物をゴムから分離した後、乾燥した。本処理を施した共重合ゴムを試料として、JIS K7237に記載された「全アミン価試験方法」により全アミノ基含有量を定量した。続けて、上記処理を施した共重合ゴムを試料として「アセチルアセトンブロックド法」により第2アミノ基および第3アミノ基の含有量を定量した。試料を溶解させる溶媒には、o−ニトロトルエンを使用、アセチルアセトンを添加し、過塩素酢酸溶液で電位差滴定を行った。全アミノ基含有量から第2アミノ基および第3アミノ基の含有量を引いて第1アミノ基含有量(mmol)を求め、分析に使用したポリマー重量を割ることで重合体に結合した第1級アミノ基含有量(mmol/kg)を求めた。
まず重合体をトルエンに溶解した後、大量のメタノール中で沈殿させることにより共重合ゴムに結合していないアミノ基含有化合物をゴムから分離した後、乾燥した。本処理を施した共重合ゴムを試料として、 「アセチル化法」により第3アミノ基含有量を定量した。試料を溶解させる溶媒には、o−ニトロトルエン+酢酸を使用、ギ酸無水酢酸混合溶液を添加し、過塩素酢酸溶液で電位差滴定を行った。定量値、第3アミノ基含有量(mmol)を分析に使用したポリマー重量を割り返すことで重合体に結合した第3級アミノ基含有量(mmol/kg)を求めた。
赤外吸収スペクトルにより、Si−C結合に起因する1,160cm−1の吸収量により求めた。
以下の実施例及び比較例で製造した共重合ゴムを用い、表2に示す配合処方に従って、250ccラボプラストミルで混練りしたのち、145℃で所定時間、加硫を行った加硫ゴムを用いて、下記(イ)〜(ニ)の各種ゴム物性の測定を行った。
(ロ)DIN摩耗指数:JIS K 6264に従って測定した。測定値を指数で表示し、数値が大きいほど摩耗量が少なく、耐摩耗性は良好であることを示す。
(ハ)反発弾性:トリプソ式反発弾性試験機を使用して、JIS K 6255に従って測定した。測定温度は25℃、50℃、80℃とした。一般に、25℃の反発弾性はウエットスキッドの指標として用いられ、数値が小さいほどウエットスキッドが良好である。一方、50℃、80℃の反発弾性は転がり抵抗の指標として用いられ、数値が大きいほど転がり抵抗が少なく、タイヤ用のゴムとして良好である。
(ニ)tanδ(70℃):米国レオメトリックス社製の動的スペクトロメーターを使用し、引張動歪0.7%、周波数15.9Hz、70℃で測定した。この数値が小さいほど、ゴム組成物のヒステリシスロスが小さく、タイヤにしたときの転がり抵抗が低減できる。
窒素置換された内容積5リットルのオートクレーブ反応器に、シクロヘキサン3,000g、テトラヒドロフラン30.0g、ドデシルベンゼンスルホン酸カリウム12.4g(0.034mmol)、スチレン205g(1.97mol)、1,3−ブタジエン145g(2.68mol)を仕込んだ。反応器内容物の温度を40℃に調整した後、重合開始剤としてn−ブチルリチウム360mg(5.62mmol)を添加して重合を開始した。重合温度が55℃に到達した時点から、ブタジエン150g(2.77mol)を15分間かけて連続的に追加し重合反応を継続した。反応器内容物の最高温度は85℃に達した。
窒素置換された内容積5リットルのオートクレーブ反応器に、シクロヘキサン3,000g、テトラヒドロフラン30.0g、スチレン200g(1.92mol)、1,3−ブタジエン150g(2.77mol)を仕込んだ。反応器内容物の温度を40℃に調整した後、重合開始剤としてn−ブチルリチウム360mg(5.62mmol)を添加して重合を開始した。重合温度が68℃に到達した時点から、ブタジエン150g(2.77mol)を10分間かけて連続的に追加し重合を継続した。反応器内容物の最高温度は80℃に達した。
窒素置換された内容積5リットルのオートクレーブ反応器に、シクロヘキサン3,000g、テトラヒドロフラン27.0g、ドデシルベンゼンスルホン酸カリウム0.05g(0.137mmol)、スチレン205g(1.97mol)、1,3−ブタジエン220g(4.07mol)を仕込んだ。反応器内容物の温度を40℃に調整した後、n−ブチルリチウム360mg(5.62mmol)を添加して重合を開始した。
重合転化率が99%に達した時点で、メチルジクロロシラン207mgを加えて15分間反応を行った。反応後の重合体溶液に、2,6−ジ−tert−ブチル−p−クレゾールを添加した後、スチームストリッピングにより脱溶媒を行った。得られた重合物を、110℃に調温された熱ロールにより乾燥して共重合ゴムを得た。このゴムを共重合ゴムCとする。得られた共重合ゴムCの組成および性質を表1に示す。
窒素置換された内容積5リットルのオートクレーブ反応器に、シクロヘキサン3,000g、テトラヒドロフラン57.0g、スチレン205g(1.97mol)、1,3−ブタジエン245g(4.53mol)を仕込んだ。反応器内容物の温度を30℃に調整した後、n−ブチルリチウム360mg(5.62mmol)を添加して重合を開始した。重合温度が70℃に到達した時点から、ブタジエン50g(0.92mol)を10分間かけて連続的に追加し重合を継続した。反応器内容物の最高温度は85℃に達した。
実施例1において、重合開始末端に第3級アミノ基を導入する目的で重合初期に2級アミンとしてのピペリジン431mg(5.06mmol)を添加し、また重合転化率が99%に達した時点で末端変性剤として添加する物質として、メチルジクロロシラン207mgに代えて、N,N−ビス(トリメチルシリル)アミノプロピルメチルジメトキシシラン1.799g(5.06mmol)を用いたこと以外は、実施例1と同様にして、共重合ゴムEを得た。得られた共重合ゴムEの組成および性質を表1に示す。この共重合ゴムEを用いて、表2に示す配合処方により調製した配合ゴムを加硫して、物性評価を行った。その結果を表3に示す。
実施例1において、重合転化率が99%に達した時点で末端変性剤として添加する物質として、メチルジクロロシラン207mgに代えて、N,N−ビス(トリメチルシリル)アミノプロピルメチルジメトキシシラン1.799gを用いたこと以外は、実施例1と同様にして、共重合ゴムFを得た。得られた共重合ゴムFの組成および性質を表1に示す。
実施例1において、重合開始末端に第3級アミノ基を導入する目的で重合初期に2級アミンとしてのピペリジン431mgを添加したこと以外は、実施例1と同様にして、共重合ゴムGを得た。得られた共重合ゴムGの組成および性質を表1に示す。
比較例3において、重合開始末端に第3級アミノ基を導入する目的で重合初期に2級アミンとしてのピペリジン431mgを添加し、また重合転化率が99%に達した時点で末端変性剤として添加する物質として、メチルジクロロシラン207mgに代えて、N,N−ビス(トリメチルシリル)アミノプロピルメチルジメトキシシラン1.799gを用いたこと以外は、比較例3と同様にして、共重合ゴムHを得た。得られた共重合ゴムHの組成および性質を表1に示す。
窒素置換された内容積5リットルのオートクレーブ反応器に、シクロヘキサン3,000g、テトラヒドロフラン30.0g、スチレン200g(1.92mol)、1,3−ブタジエン150g(2.77mol)を仕込んだ。反応器内容物の温度を40℃に調整した後、重合開始剤としてn−ブチルリチウム360mg(5.62mmol)を添加して重合を開始した。重合温度が68℃に到達した時点から、ブタジエン150g(2.77mol)を10分間かけて連続的に追加し重合反応を継続した。反応器内容物の最高温度は80℃に達した。
ルメチルジメトキシシラン1.799g(5.06mmol)を加えて15分間反応を行った。15分の反応終了後の重合体溶液に、2,6−ジ−tert−ブチル−p−クレゾールを添加した後、スチームストリッピングにより脱溶媒を行った。得られた重合物を、110℃に調温された熱ロールにより乾燥して共重合ゴムを得た。このゴムを共重合ゴムJとする。得られた共重合ゴムJの組成および性質を表4に示す。
窒素置換された内容積5リットルのオートクレーブ反応器に、シクロヘキサン3,000g、テトラヒドロフラン27.0g、スチレン205g(1.97mol)、1,3−ブタジエン245g(4.53mol)を仕込んだ。反応器内容物の温度を30℃に調整した後、n−ブチルリチウム360mg(5.62mmol)を添加して重合を開始した。重合温度が70℃に到達した時点でから、ブタジエン50g(0.92mol)を10分間かけて連続的に追加し重合を継続した。反応器内容物の最高温度は85℃に達した。
実施例5において、重合開始末端に第3級アミノ基を導入する目的で重合初期に2級アミンとしてのピペリジン431mgを添加したこと以外は、実施例5と同様にして、共重合ゴムLを得た。得られた共重合ゴムLの組成および性質を表4に示す。
この共重合ゴムLを用いて、表2に示す配合処方により調製した配合ゴムを加硫して、物性評価を行った。その結果を表5に示す。
窒素置換された内容積5リットルのオートクレーブ反応器に、シクロヘキサン3,000g、テトラヒドロフラン27.0g、ドデシルベンゼンスルホン酸カリウム0.05g(0.137mmol)、ピペリジン431mg、スチレン205g(1.97mol)、1,3−ブタジエン220g(4.07mol)を仕込んだ。反応器内容物の温度を40℃に調整した後、n−ブチルリチウム360mg(5.62mmol)を添加して重合を開始した。
窒素置換された内容積5リットルのオートクレーブ反応器に、シクロヘキサン3,000g、テトラヒドロフラン30.0g、ピペリジン431mg、スチレン200g(1.92mol)、1,3−ブタジエン150g(2.77mol)を仕込んだ。反応器内容物の温度を40℃に調整した後、重合開始剤としてn−ブチルリチウム360mg(5.62mmol)を添加して重合を開始した。重合温度が68℃に到達した時点から、ブタジエン150g(2.77mol)を10分間かけて連続的に追加し重合反応を継続した。反応器内容物の最高温度は80℃に達した。
窒素置換された内容積5リットルのオートクレーブ反応器に、シクロヘキサン3,000g、テトラヒドロフラン57.0g、ピペリジン431mg、スチレン205g(1.97mol)、1,3−ブタジエン245g(4.53mol)を仕込んだ。反応器内容物の温度を30℃に調整した後、重合開始剤としてn−ブチルリチウム360mg(5.62mmol)を添加して重合を開始した。重合温度が70℃に到達した時点から、ブタジエン50g(0.92mol)を10分間かけて連続的に追加し重合を継続した。反応器内容物の最高温度は85℃に達した。
窒素置換された内容積5リットルのオートクレーブ反応器に、シクロヘキサン3,000g、テトラヒドロフラン27.0g、ドデシルベンゼンスルホン酸カリウム0.05g(0.137mmol)、スチレン205g(1.97mol)、1,3−ブタジエン220g(4.07mol)を仕込んだ。反応器内容物の温度を40℃に調整した後、n−ブチルリチウム360mg(5.62mmol)を添加して重合を開始した。重合温度が55℃に到達した時点から、ブタジエン75g(1.39mol)を10分間かけて連続的に追加し重合を継続した。最高温度は83℃に達した。重合転化率が99%に達した時点で、N,N−ビス(トリメチルシリル)アミノプロピルメチルジメトキシシラン1.799g(5.06mmol)を加えて15分間反応を行った。反応終了後の重合体溶液に、2,6−ジ−tert−ブチル−p−クレゾールを添加した後、スチームストリッピングにより脱溶媒を行った。得られた共重合物を110℃に調温された熱ロールによりゴムを乾燥した。このゴムを共重合ゴムQとする。得られた共重合ゴムQの組成および物性を表6に示す。
Claims (17)
- 共役ジオレフィンと芳香族ビニル化合物との共重合ゴムであって、
(1)共重合体鎖に結合した第1級アミノ基とアルコキシシリル基とを有しており、
(2)芳香族ビニル化合物の重合単位の含有量が共重合ゴムの5重量%以上60重量%以下であり、
(3)芳香族ビニル化合物が共重合ゴムの共重合体鎖の片方の端部に密に、他方の端部に粗に分布しており、かつ
(4)差動走査熱量計(DSC)によって分析される吸熱曲線におけるガラス転移温度域での変曲点間の温度差(△Tg)が25℃以上、
である、共役ジオレフィン共重合ゴム。 - 芳香族ビニル化合物の重合単位が1個の芳香族ビニル化合物単鎖が全結合芳香族ビニル化合物の40質量%未満であり、かつ芳香族ビニル化合物単位が2〜7個連なった芳香族ビニル化合物連鎖が全結合芳香族ビニル化合物の50質量%以上である、請求項1に記載の共役ジオレフィン共重合ゴム。
- ヘテロ原子として窒素を含む有機化合物を開始剤として、共役ジオレフィンと芳香族ビニル化合物との共重合によって得られる、請求項1に記載の共役ジオレフィン共重合ゴム。
- 第1級アミノ基の含有量が0.5〜200mmol/kg・共重合ゴムポリマーであり、そしてアルコキシシリル基の含有量が0.5〜200mmol/kg・共重合ゴムポリマーである、請求項1に記載の共役ジオレフィン共重合ゴム。
- ガラス転移温度域での変曲点間の温度差△Tgが、30℃以上である、請求項1〜4のいずれか1項に記載の共役ジオレフィン共重合ゴム。
- ルイス塩基を含有する炭化水素溶媒中で、有機アルカリ金属化合物および有機アルカリ土類金属化合物、リチウムアミド化合物よりなる群から選ばれる少なくとも1種の化合物を開始剤として用いて、共役ジオレフィンと芳香族ビニル化合物を共重合するに際して、反応媒体中にカリウム化合物を添加するとともに、重合反応の開始時に芳香族ビニル化合物と共役ジオレフィンとのモル比が0.5以上の割合となるモノマー組成で重合反応を行うことを含む、共役ジオレフィン共重合ゴムを製造する方法。
- さらに、重合反応により得られた重合活性末端と下記式(3)
または下記式(4)
で表わされる少なくとも1つのアミノ基含有アルコキシシラン化合物を反応させ、しかる後加水分解することにより、共役ジオレフィン共重合ゴムを製造する、請求項7に記載の方法。 - 上記アミノ基含有アルコキシシラン化合物が、N,N−ビス(トリメチルシリル)アミノプロピルメチルジメトキシシラン、N,N−ビス(トリメチルシリル)アミノプロピルメチルジエトキシシランまたは1−トリメチルシリル−2,2−ジメトキシ−1−アザ−2−シラシクロペンタンである、請求項8に記載の方法。
- ルイス塩基を含有する炭化水素溶媒中で、下記式(5)
(R4R5R6Si)2−N−R1−Li (5)
[ここで、R1の定義は上記式(1)に同じであり、R4,R5およびR6の定義は、上記式(3)に同じである]、
または、下記式(6)
で表わされるリチウムアミド開始剤を用いて、共役ジオレフィンと芳香族ビニル化合物をアニオン重合させるに際し、反応媒体中にカリウム化合物を添加するとともに、重合反応の開始時に芳香族ビニル化合物と共役ジオレフィンとのモル比が0.5以上の割合となるモノマー組成で重合反応を行い、
そのようにして得られた重合活性末端と、
下記式(7)
で表わされるアルコキシシラン化合物を反応させることにより、共役ジオレフィン共重合ゴムを製造する、請求項7に記載の方法。 - 重合反応の初期に芳香族ビニル化合物が過剰の状態で反応を行い、重合反応の後半に全モノマーの30モル%以上の共役ジオレフィンを追加添加する、請求項7〜10のいずれかに記載の方法。
- カリウム化合物が、有機スルホン酸カリウム塩、有機カルボン酸カリウム塩、カリウムアルコキシド、カリウムフェノキシド及び有機亜燐酸エステルのカリウム塩からなる群から選ばれる化合物であることを特徴とする、請求項7〜11のいずれかに記載の方法。
- カリウム化合物を、開始剤の有機アルカリ金属、有機アルカリ土類金属、又はリチウムアミドから選ばれる開始剤の1g原子あたり0.01〜0.5モル用いる、請求項7〜12に記載の方法。
- 請求項1〜6のいずれかに記載の共役ジオレフィン共重合ゴム100質量部に対し、伸展油10〜100質量部を含有してなる、油展共重合ゴム。
- 請求項1〜6のいずれかに記載の共役ジオレフィン共重合ゴムが全ゴム成分の30重量%以上を占める全ゴム成分100質量部に対し、フィラー20〜120質量部を含有してなる、ゴム組成物。
- 上記フィラーの少なくとも1質量部がシリカであり、さらにシリカ100質量部に対してシランカップリング剤を0.5〜20重量部含有する請求項15に記載のゴム組成物。
- 請求項15または16に記載のゴム組成物をトレッド部材に用いたタイヤ。
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US20160009903A1 (en) * | 2013-02-28 | 2016-01-14 | Jsr Corporation | Modified conjugated diene polymer and method for producing same, polymer composition, crosslinked polymer, and tire |
US20160122501A1 (en) * | 2013-03-25 | 2016-05-05 | Etic Inc. | Rubber composition comprising emulsion-polymerized conjugated diene polymer and silica suspension, and method for producing same |
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WO2015199226A1 (ja) * | 2014-06-27 | 2015-12-30 | 日本ゼオン株式会社 | 共役ジエン系ゴムの製造方法 |
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