JP6795962B2 - 窒素基を含有する官能化エラストマー - Google Patents
窒素基を含有する官能化エラストマー Download PDFInfo
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- JP6795962B2 JP6795962B2 JP2016245077A JP2016245077A JP6795962B2 JP 6795962 B2 JP6795962 B2 JP 6795962B2 JP 2016245077 A JP2016245077 A JP 2016245077A JP 2016245077 A JP2016245077 A JP 2016245077A JP 6795962 B2 JP6795962 B2 JP 6795962B2
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- branched alkyl
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- 229920001971 elastomer Polymers 0.000 title claims description 65
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims description 13
- 239000000806 elastomer Substances 0.000 title description 10
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 60
- 239000005060 rubber Substances 0.000 claims description 55
- 239000000178 monomer Substances 0.000 claims description 52
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- 229920001577 copolymer Polymers 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 23
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 22
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- 239000011593 sulfur Substances 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 239000002685 polymerization catalyst Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
- 229920000642 polymer Polymers 0.000 description 32
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 24
- 238000006116 polymerization reaction Methods 0.000 description 21
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 150000001993 dienes Chemical class 0.000 description 17
- 239000000377 silicon dioxide Substances 0.000 description 17
- 238000000034 method Methods 0.000 description 16
- 239000003054 catalyst Substances 0.000 description 15
- 239000003921 oil Substances 0.000 description 15
- 235000019198 oils Nutrition 0.000 description 15
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 12
- -1 trifluoroethoxy-4-oxobutyl Chemical group 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000011777 magnesium Substances 0.000 description 11
- 239000005062 Polybutadiene Substances 0.000 description 10
- 239000006229 carbon black Substances 0.000 description 10
- 235000019241 carbon black Nutrition 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000007334 copolymerization reaction Methods 0.000 description 8
- 150000003961 organosilicon compounds Chemical class 0.000 description 8
- 229920002857 polybutadiene Polymers 0.000 description 8
- ZZAKVYWMARSNNU-UHFFFAOYSA-N 9-[[4-(2-methylidenebut-3-enyl)phenyl]methyl]carbazole Chemical compound C=C(CC1=CC=C(CN2C3=CC=CC=C3C=3C=CC=CC2=3)C=C1)C=C ZZAKVYWMARSNNU-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 239000010734 process oil Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000004073 vulcanization Methods 0.000 description 6
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 5
- VZVOSTHLVPOIQH-UHFFFAOYSA-N 9-(5-methylidenehept-6-enyl)carbazole Chemical compound C=C(CCCCN1C2=CC=CC=C2C=2C=CC=CC1=2)C=C VZVOSTHLVPOIQH-UHFFFAOYSA-N 0.000 description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- AQXDXGPVNIEMPO-UHFFFAOYSA-N N,N-dimethyl-2-(2-methylidenebut-3-enyl)aniline Chemical compound CN(C1=C(C=CC=C1)CC(C=C)=C)C AQXDXGPVNIEMPO-UHFFFAOYSA-N 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 5
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- RSWAJWUBVSLITB-UHFFFAOYSA-N N-(5-methylidenehept-6-enyl)-N-phenylaniline Chemical compound C=C(CCCCN(C1=CC=CC=C1)C1=CC=CC=C1)C=C RSWAJWUBVSLITB-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000007720 emulsion polymerization reaction Methods 0.000 description 4
- 150000004795 grignard reagents Chemical class 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
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- 239000007787 solid Substances 0.000 description 4
- 230000000930 thermomechanical effect Effects 0.000 description 4
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 3
- QVDVATMGFDDWPU-UHFFFAOYSA-N 4-buta-1,3-dien-2-yl-n,n-dimethylaniline Chemical compound CN(C)C1=CC=C(C(=C)C=C)C=C1 QVDVATMGFDDWPU-UHFFFAOYSA-N 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- FXKAQTPVBKDEOS-UHFFFAOYSA-N [Li]CC1=CC=CC=C1N(C)C Chemical compound [Li]CC1=CC=CC=C1N(C)C FXKAQTPVBKDEOS-UHFFFAOYSA-N 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 3
- 229920003211 cis-1,4-polyisoprene Polymers 0.000 description 3
- 239000012967 coordination catalyst Substances 0.000 description 3
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 238000010058 rubber compounding Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 229920001897 terpolymer Polymers 0.000 description 3
- ZGHFDIIVVIFNPS-UHFFFAOYSA-N 3-Methyl-3-buten-2-one Chemical compound CC(=C)C(C)=O ZGHFDIIVVIFNPS-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- RTACIUYXLGWTAE-UHFFFAOYSA-N buta-1,3-diene;2-methylbuta-1,3-diene;styrene Chemical compound C=CC=C.CC(=C)C=C.C=CC1=CC=CC=C1 RTACIUYXLGWTAE-UHFFFAOYSA-N 0.000 description 2
- 229920005549 butyl rubber Polymers 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 229920003193 cis-1,4-polybutadiene polymer Polymers 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000012990 dithiocarbamate Substances 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
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- 239000012535 impurity Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- DQEUYIQDSMINEY-UHFFFAOYSA-M magnesium;prop-1-ene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C=C DQEUYIQDSMINEY-UHFFFAOYSA-M 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
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- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- CBXRMKZFYQISIV-UHFFFAOYSA-N 1-n,1-n,1-n',1-n',2-n,2-n,2-n',2-n'-octamethylethene-1,1,2,2-tetramine Chemical compound CN(C)C(N(C)C)=C(N(C)C)N(C)C CBXRMKZFYQISIV-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
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- LLMLGZUZTFMXSA-UHFFFAOYSA-N 2,3,4,5,6-pentachlorobenzenethiol Chemical class SC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LLMLGZUZTFMXSA-UHFFFAOYSA-N 0.000 description 1
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- XYZWMVYYUIMRIZ-UHFFFAOYSA-N 4-bromo-n,n-dimethylaniline Chemical compound CN(C)C1=CC=C(Br)C=C1 XYZWMVYYUIMRIZ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- URUMPUZGKXOPRI-UHFFFAOYSA-N 9-(4-chlorobutyl)carbazole Chemical compound C1=CC=C2N(CCCCCl)C3=CC=CC=C3C2=C1 URUMPUZGKXOPRI-UHFFFAOYSA-N 0.000 description 1
- ZZGKNPBZECSTOY-UHFFFAOYSA-N 9-[[4-(chloromethyl)phenyl]methyl]carbazole Chemical compound ClCC1=CC=C(CN2C3=CC=CC=C3C=3C=CC=CC2=3)C=C1 ZZGKNPBZECSTOY-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 238000004438 BET method Methods 0.000 description 1
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
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- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 description 1
- RVZIFMHGRUYFJH-UHFFFAOYSA-N N-(4-bromobutyl)-N-phenylaniline Chemical compound BrCCCCN(C1=CC=CC=C1)C1=CC=CC=C1 RVZIFMHGRUYFJH-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
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- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
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- HFKJQIJFRMRSKM-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenoxy]boronic acid Chemical compound OB(O)OC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 HFKJQIJFRMRSKM-UHFFFAOYSA-N 0.000 description 1
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- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
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- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
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- 229910052744 lithium Inorganic materials 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000004200 microcrystalline wax Substances 0.000 description 1
- 235000019808 microcrystalline wax Nutrition 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- JDEJGVSZUIJWBM-UHFFFAOYSA-N n,n,2-trimethylaniline Chemical compound CN(C)C1=CC=CC=C1C JDEJGVSZUIJWBM-UHFFFAOYSA-N 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 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 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N penta-1,3-diene Chemical compound CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- JPPLPDOXWBVPCW-UHFFFAOYSA-N s-(3-triethoxysilylpropyl) octanethioate Chemical compound CCCCCCCC(=O)SCCC[Si](OCC)(OCC)OCC JPPLPDOXWBVPCW-UHFFFAOYSA-N 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical group [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F36/14—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated containing elements other than carbon and hydrogen
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
- C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C1/0016—Compositions of the tread
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- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F36/06—Butadiene
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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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
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F36/08—Isoprene
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- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/72—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from metals not provided for in group C08F4/44
- C08F4/80—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from metals not provided for in group C08F4/44 selected from iron group metals or platinum group metals
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- C08F4/00—Polymerisation catalysts
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- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
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- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/619—Component covered by group C08F4/60 containing a transition metal-carbon bond
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Description
立体規則ジエンポリマーは、タイヤコンパウンドの重要な成分として工業的に大規模に製造及び使用されている。高レベルの立体規則性を有するジエンポリマーは、ほぼ例外なく配位重合触媒を用いて製造されるが、配位重合触媒は一般に極性官能基によって害されやすい。この有害作用のために、配位触媒と適合可能なモノマーの種類は通常、単純な炭化水素に限定される。タイヤ業界では周知のことであるが、たとえ低レベルの官能性でも、ある種のタイヤポリマー(アニオン重合又は乳化重合により製造)に組み込まれると、そのようなポリマーを含有するタイヤの性能が著しく改良される。残念なことに、この官能化技術を立体規則ジエンポリマーに適用するための確かな方法は現在のところない。しかしながら、そのようなポリマーがあれば、おそらく公知の非官能化ポリマーに優る優れたタイヤ特性を示すであろう。
さらに、そのようなコポリマーの製造法も開示する。
一態様において、非官能化ジエンモノマーは、1,3−ブタジエン又はイソプレンである。
コポリマーは高度の立体規則性を有している。一態様において、コポリマーは、コポリマーのポリブタジエン含量を基にして80重量パーセントを超えるシス1,4ミクロ構造含量を有している。一態様において、コポリマーは、コポリマーのポリブタジエン含量を基にして95重量パーセントを超えるシス1,4ミクロ構造含量を有している。
(アリル)(アレーン)Ni(II)触媒を用いる重合は、O’Connorら(Journal of Applied Polymer Science,Part A:Polymer Chemistry,Vol.48,1901−1912(2010))に記載の方法に従って実施することができる。共重合は、0〜60℃の範囲の温度で溶液重合によって実施することができる。溶液重合のための適切な溶媒は、トルエン、塩化メチレン、及びヘプタンなどである。
ゴム組成物は、官能化コポリマーに加えて、任意にオレフィン性不飽和を含有する一つ又は複数のゴム又はエラストマーを含んでいてもよい。“オレフィン性不飽和を含有するゴム又はエラストマー”又は“ジエン系エラストマー”という語句は、天然ゴム及びその各種未加工形及び再生形、ならびに各種合成ゴムのどちらも含むものとする。本発明の記載において、“ゴム”及び“エラストマー”という用語は、別段の規定のない限り互換的に使用されうる。“ゴム組成物”、“配合ゴム”及び“ゴムコンパウンド”という用語は、各種成分及び材料とブレンド又は混合されているゴムのことを言うのに互換的に使用され、そのような用語はゴム混合又はゴム配合分野の当業者には周知である。代表的な合成ポリマーは、ブタジエン及びその同族体及び誘導体、例えばメチルブタジエン、ジメチルブタジエン及びペンタジエンのホモ重合生成物、ならびにブタジエン又はその同族体もしくは誘導体とその他の不飽和モノマーとから形成されるようなコポリマーである。後者に含まれるものとしては、アセチレン、例えばビニルアセチレン;オレフィン、例えばイソブチレン(イソプレンと共重合してブチルゴムを形成する);ビニル化合物、例えばアクリル酸、アクリロニトリル(ブタジエンと重合してNBRを形成する)、メタクリル酸及びスチレン(後者の化合物はブタジエンと重合してSBRを形成する)のほか、ビニルエステル及び各種不飽和アルデヒド、ケトン及びエーテル、例えばアクロレイン、メチルイソプロペニルケトン及びビニルエチルエーテルなどが挙げられる。合成ゴムの具体例は、ネオプレン(ポリクロロプレン)、ポリブタジエン(シス−1,4−ポリブタジエンを含む)、ポリイソプレン(シス−1,4−ポリイソプレンを含む)、ブチルゴム、ハロブチルゴム、例えばクロロブチルゴム又はブロモブチルゴム、スチレン/イソプレン/ブタジエンゴム、1,3−ブタジエン又はイソプレンとスチレン、アクリロニトリル及びメチルメタクリレートなどのモノマーとのコポリマー、ならびにエチレン/プロピレンターポリマー(エチレン/プロピレン/ジエンモノマー(EPDM)としても知られる)、特にエチレン/プロピレン/ジシクロペンタジエンターポリマーなどである。使用できるゴムの追加例は、アルコキシ−シリル末端官能化溶液重合ポリマー(SBR、PBR、IBR及びSIBR)、ケイ素結合及びスズ結合星状枝分れポリマーなどである。好適なゴム又はエラストマーはポリイソプレン(天然又は合成)、ポリブタジエン及びSBRである。
本明細書中で使用され、従来の慣例に従う用語“phr”は、“100重量部のゴム、又はエラストマーあたりの各材料の重量部”を意味する。
ゴム組成物は、約1〜約150phrのシリカを含みうる。別の態様においては、10〜100phrのシリカが使用されうる。
従来型シリカは、電子顕微鏡による測定で例えば0.01〜0.05ミクロンの範囲の平均極限粒径を有すると予測されうるが、シリカ粒子は、それよりさらに小さい、又はおそらくは大きいサイズであってもよい。
他のフィラーもゴム組成物に使用できる。例えば、超高分子量ポリエチレン(UHMWPE)などの粒子状フィラー、米国特許第6,242,534号;6,207,757号;6,133,364号;6,372,857号;5,395,891号;又は6,127,488号に開示されているような架橋粒子状ポリマーゲル、及び米国特許第5,672,639号に開示されているような可塑化デンプン複合フィラーなどであるが、これらに限定されない。そのようなその他のフィラーは1〜30phrの範囲の量で使用されうる。
Ni触媒IIの合成は文献に記載されている(O’Connorら,Organometallics 2009,28 2372−2384)。あるいは、この錯体のMg塩と過剰のNaBArF 4の混合物を実施例2で概要を示した手順に従って製造することもできる。
本実施例では、Ni(II)配位触媒の合成について説明する。式IIIの化合物は以下のようにして式IIの化合物に変換された。化合物III(8mmol)をNaBArF 4(8mmol)及びメシチレン(20mmol)と、100mlシュレンクチューブ内の40mlジエチルエーテル中で混合し、−78℃に冷却した。5分後、ジエチルエーテル中1Mのアリルマグネシウムブロミド8mlを撹拌下で滴加し、アリルマグネシウムブロミドの添加完了後、冷却浴の交換により、温度を−20℃に上げた。−20℃で60分後、冷却浴を取り除き、混合物を25℃に温めた。この温度でエーテルは蒸留除去され、粗固体が残った。次に、塩化メチレン(30ml)を加え、混合物を撹拌した後、固体をろ過した。ヘプタン(10mL)を塩化メチレン溶液に加え、得られた混合物を高真空下で濃縮乾固し、約50%の収率のNiベースの触媒IIを含有する6.85gの固体を得た。
以下の実施例において、1,3-ブタジエン及びイソプレンと、9−(5−メチレンヘプタ−6−エン−1−イル)−9H−カルバゾール(式IV)との共重合を示す。官能性モノマーの9−(5−メチレンヘプタ−6−エン−1−イル)−9H−カルバゾールは以下のようにして合成した。
1H NMR (400 MHz, C6D6) δ = 8.06 (m, 2H, H13), 7.41 (m, 2H, H11), 7.23 (m, 2H, H12), 7.16 (m, 2H, H10), 6.27 (dd, J = 17.6, 10.8 Hz, 1H, H13), 5.05 (d, J = 17.6 Hz, 1H, H4), 4.92 (d, J = 10.8 Hz, 1H, H4), 4.89 (s, 1H, H1), 4.77 (s, 1H, H1), 3.76 (t, J= 7.2 Hz, 2H, H8), 1.92 (t, J = 7.6 Hz, 2H, H5), 1.48 (m, 2H, H6), 1.28 (m, 2H, H7)。
13C NMR (100 MHz, C6D6) δ = 146.0 (C2), 140.8 (C9, 139.1 (C3), 125.9 (C12), 123.5 (C14), 120.8 (C13), 119.2 (C11), 116.9 (C1), 113.2 (C4), 108.9 (C10), 42.7 (C8), 31.1 (C5), 28.8 (C6), 25.7 (C7)。
トルエン中での化合物IIを用いる1,3-ブタジエンと9−(5−メチレンヘプタ−6−エン−1−イル)−9H−カルバゾールの共重合
式IVの官能性モノマーは実施例3に記載のようにして合成した。
本実施例では、9−(4−(2−メチレンブタ−3−エン−1−イル)ベンジル)−9H−カルバゾールの合成を示す。官能性モノマーの9−(4−(2−メチレンブタ−3−エン−1−イル)ベンジル)−9H−カルバゾール(式V)は、以下のようにして合成した。
1H NMR (400 MHz, C6D6) δ = 8.06 (d, J = 7.9 Hz, 2H, H17 及び H20), 7.31 (vt, J = 7.5 Hz, 2H, H15 及び H22), 7.21 (vt, J = 7.5 Hz, 2H, H16 及び 21), 7.10 (d, J = 8.2 Hz, 2H, H14 及び H23), 6.85 (d, J = 7.8 Hz, 2H, H7 及び 11), 6.80 (d, J = 7.8 Hz, 2H, H8 及び 10), 6.29 (dd, J = 17.5, 10.8 Hz, 1H, H3), 5.07 (d, J = 17.5 Hz, 1H, H4), 4.98 (s, 1H, H1), 4.93 (s, 2H, H12), 4.88 (d, J = 10.8 Hz, 1H, H4), 4.75 (s, 1H, H1), 3.27 (s, 2H, H5)。
13C NMR (100 MHz, C6D6) δ = 145.5 (C2), 141.2 (C13 及び C24), 138.8 (C3), 138.7 (C6), 135.4 (C9), 129.5 (C7 及び C11), 126.5 (C8 及び C10), 126.2 (C15 及びC22), 123.7 (C18 及び C19), 120.8 (C17 及び C20), 119.6 (C16 及び C21), 118.3 (C1), 114.5 (C4), 109.3 (C14 及び C23), 46.2 (C12), 37.9 (C5)。
トルエン中での化合物IIを用いる1,3-ブタジエンと9−(4−(2−メチレンブタ−3−エン−1−イル)ベンジル)−9H−カルバゾールの共重合
式Vの官能性モノマーは実施例5に記載のようにして合成した。
本実施例では、N−(5−メチレンヘプタ−6−エン−1−イル)−N−フェニルアニリンの合成を示す。官能性モノマーのN−(5−メチレンヘプタ−6−エン−1−イル)−N−フェニルアニリン(式VI)は、以下のようにして合成した。
1H-NMR (400 MHz, C6D6): δ = 7.15 - 7.10 (m, 4H, H10, H14, H16, 及び H20), 6.98 - 6.95 (m, 4H, H11, H13, H17, 及び H19), 6.86 - 6.82 (m, 2H, H12 及び H18), 6.29 (dd, 3J = 17.6 及び 10.8 Hz, 1H, H3), 5.08 (d, J = 17.6 Hz, 1H, H4), 4.93 (m, 1H, H4), 4.92 (m, 1H, H1), 4.85 (m, 1H, H1), 3.49 (t, J = 7.5 Hz, 2H, H8), 2.01 (td, 3J = 7.6 及び 4J = 1.2 Hz, 2H, H5), 1.53 (m, 2H, H7), 1.35 (m, 2H, H6)。
13C-NMR (100 MHz, C6D6): δ = 148.7 (C19 及び C20), 146.5 (C2), 139.2 (C3), 129.5 (C11, C13, C17, 及び C19) 121.5 (C12 及び C18), 121.4 (C10, C14, C16, 及び C20), 115.8 (C4), 113.2 (C1), 52.3 (C8), 31.3 (C5), 27.7 (C7), 25.8 (C6)
トルエン中での化合物IIを用いる1,3-ブタジエンとN−(5−メチレンヘプタ−6−エン−1−イル)−N−フェニルアニリンの共重合
式VIの官能性モノマーは実施例7に記載のようにして合成した。
本実施例では、4−(ブタ−1,3−ジエン−2−イル)−N,N−ジメチルアニリンの合成を示す。官能性モノマーの4−(ブタ−1,3−ジエン−2−イル)−N,N−ジメチルアニリン(式VII)は、以下のようにして合成した。
1H NMR (400 MHz, C6D6): d 7.36 (m, 2H, H6 及び H10), 6.66 (dd, 3J = 17.6 及び 10.8 Hz, 1H, H3), 6.56 (m, 2H, H7 及び H9), 5.45 (d, , 3J = 17.6, 1H, H4), 5.25 (s, 1H, H1), 5.20 (s, 1H, H1), 5.14 (d, 3J = 10.8, 1H, H4), 2.50 (s, 6H, H11 及び H12)。
本実施例では、1,3-ブタジエンと4−(ブタ−1,3−ジエン−2−イル)−N,N−ジメチルアニリンの共重合を示す。
ヘプタン溶液中の式VIIのモノマー(1mmol/1.17gヘプタン溶液)を、14mLのトルエンを含有する火炎乾燥シュレンクフラスコに加え、次いでフラスコをゴムセプタムで密封した。ブタジエンを、反応温度及び1.05barの圧力でのトルエンの飽和により添加した。トルエン(5mL)中触媒を示された反応温度で添加することにより重合を開始した。重合は、示された時間、その温度で行わせた。0.5mLのNEt3を加えて重合を終了させた。残留ブタジエンを減圧下で注意深く除去し、ポリマーを、BHTの存在下(約100mg/100mL)、MeOH中に沈殿させた。形成されたポリマーを減圧下50℃で一晩乾燥させ、示された収量gのポリ(ブタジエン−コ−4−(ブタ−1,3−ジエン−2−イル)−N,N−ジメチルアニリン)を得た。サンプルを分析し、結果を表4に示した。分子量Mn及び多分散性(PDI)は、THF中でのGPCを用い、ポリスチレン標準に対して測定した。ガラス転移温度TgはDSCを用いて測定した。ポリマーのミクロ構造は、NMR分析(1H及び13C)により決定した。
本実施例では、N,N−ジメチル−2−(2−メチレンブタ−3−エン−1−イル)アニリンの合成を示す。官能性モノマーのN,N−ジメチル−2−(2−メチレンブタ−3−エン−1−イル)アニリン(式VIII)は、以下のようにして合成した。
1H NMR (400 MHz, C6D6/thf-h8): d 7.13 (m, 1H, H7), 7.05 (m, 1H, H9), 6.94 (m, 1H, H10), 6.88 (m, 1H, H8), 6.35 (dd, 3J = 17.6 及び 10.8 Hz, 1H, H3), 5.20 (d, 3J = 17.6,Hz, 1H, H4), 5.04 (s, 1H, H1), 4.89 (d, 3J = 10.8 Hz, 1H, H4), 4.87 (s, 1H, H1), 3.62 (s, 2H, H5), 2.45 (s, 6H, H11 及び H12)。
本実施例では、1,3-ブタジエンとN,N−ジメチル−2−(2−メチレンブタ−3−エン−1−イル)アニリンの共重合を示す。
式VIIIのモノマーのヘプタン溶液を、15mLのトルエンを含有する火炎乾燥シュレンクフラスコに加え、次いでフラスコをゴムセプタムで密封した。ブタジエンを、反応温度及び1.05barの圧力でのトルエンの飽和により添加した。トルエン(5mL)中触媒を示された反応温度で添加することにより重合を開始した。重合は、示された時間、その温度で行わせた。0.5mLのNEt3を加えて重合を終了させた。残留ブタジエンを減圧下で注意深く除去し、ポリマーを、BHTの存在下(約100mg/100mL)、MeOH中に沈殿させた。形成されたポリマーを減圧下50℃で一晩乾燥させ、示された収量gのポリ(ブタジエン−コ−N,N−ジメチル−2−(2−メチレンブタ−3−エン−1−イル)アニリン)を得た。サンプルを分析し、結果を表5に示した。分子量Mn及び多分散性(PDI)は、THF中でのGPCを用い、ポリスチレン標準に対して測定した。ガラス転移温度TgはDSCを用いて測定した。ポリマーのミクロ構造は、NMR分析(1H及び13C)により決定した。
1.1,3−ブタジエン及びイソプレンからなる群から選ばれるモノマーと、式I:
4.少なくとも95重量パーセントのシス1,4ミクロ構造含量を含む、1記載のコポリマー。
6.0.5〜20重量パーセントの、式Iのモノマーから誘導された単位を含む、1記載のコポリマー。
8.式Iのモノマーが、構造:
10.1記載のコポリマーを含むゴム組成物。
11.10記載のゴム組成物を含む空気入りタイヤ。
14.重合触媒が、式II:
15.窒素含有ヘテロサイクリック基が、構造:
Claims (5)
- 1,3−ブタジエン及びイソプレンからなる群から選ばれるモノマーと、式I:
[式中、R1は、フェニレン、又は2〜10個の炭素原子を含有する直鎖又は分枝アルカンジイル基、又は一つもしくは複数のフェニレン基と一つもしくは複数の1〜10個の炭素原子を含有する直鎖又は分枝アルカンジイル基との組合せであり;R2及びR3は、独立に、フェニル又は1〜10個の炭素原子を含有する直鎖又は分枝アルキル基であるか、又はR2及びR3の一方は水素で、他方はフェニル又は1〜10個の炭素原子を含有する直鎖又は分枝アルキル基であるか、又はR2及びR3は窒素原子と一緒になって、4〜12個の炭素原子を含有する窒素含有ヘテロサイクリック基を表し;そしてR4は、水素又は1〜10個の炭素原子を含有する直鎖又は分枝アルキル基である]のモノマーとのコポリマー。 - 請求項1に記載のコポリマーを含むゴム組成物を特徴とする空気入りタイヤ。
- 1,3−ブタジエン及びイソプレンからなる群から選ばれるモノマーと、式I:
[式中、R1は、フェニレン、又は2〜10個の炭素原子を含有する直鎖又は分枝アルカンジイル基、又は一つもしくは複数のフェニレン基と一つもしくは複数の1〜10個の炭素原子を含有する直鎖又は分枝アルカンジイル基との組合せであり;R2及びR3は、独立に、フェニル又は1〜10個の炭素原子を含有する直鎖又は分枝アルキル基であるか、又はR2及びR3の一方は水素で、他方はフェニル又は1〜10個の炭素原子を含有する直鎖又は分枝アルキル基であるか、又はR2及びR3は窒素原子と一緒になって、4〜12個の炭素原子を含有する窒素含有ヘテロサイクリック基を表し;そしてR4は、水素又は1〜10個の炭素原子を含有する直鎖又は分枝アルキル基である]のモノマーとを(アリル)(アレーン)Ni(II)重合触媒の存在下で重合させる工程を特徴とするコポリマーの製造法。
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US9580532B1 (en) * | 2016-07-12 | 2017-02-28 | The Goodyear Tire & Rubber Company | Functionalized elastomer via allylboration |
US9574024B1 (en) * | 2016-07-12 | 2017-02-21 | The Goodyear Tire & Rubber Company | Method of making a functionalized elastomer via allylboration |
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US10301400B2 (en) | 2017-08-15 | 2019-05-28 | The Goodyear Tire & Rubber Company | Method of making a functionalized elastomer |
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US10919989B2 (en) | 2017-10-20 | 2021-02-16 | Iowa State University Research Foundation, Inc. | End group functionalization agents for polydiene |
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US11492426B2 (en) | 2020-08-07 | 2022-11-08 | The Goodyear Tire & Rubber Company | Functionalized polymer, rubber composition and pneumatic tire |
Family Cites Families (45)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1450271A (fr) * | 1964-10-29 | 1966-05-06 | Stauffer Chemical Co | Alcadiényl silanes et leurs dérivés polysiloxanes |
DE2031213C3 (de) | 1970-06-20 | 1978-09-14 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Verfahren zur Herstellung von Dimethylsulfonium-butadien-halogeniden |
US4147880A (en) | 1971-06-15 | 1979-04-03 | The Goodyear Tire & Rubber Company | Age resisters and age resistant polymeric compositions |
CA1014296A (en) * | 1973-11-08 | 1977-07-19 | Ernest J. Buckler | Amine modified polymers |
DE3670642D1 (de) | 1985-01-23 | 1990-05-31 | Nissan Chemical Ind Ltd | Polymere von substituierten 1,3-butadienverbindungen und verfahren zu deren herstellung. |
GB2217705A (en) | 1988-04-25 | 1989-11-01 | Bayer Ag | 1-Thio-substituted butadienes |
FR2669341A1 (fr) * | 1990-11-15 | 1992-05-22 | Rhone Poulenc Chimie | Polyorganosiloxane a reste(s) butadienyle(s), ses procedes de preparation et les compositions qui en derivent reticulables en un elastomere. |
DE4220563A1 (de) | 1992-06-24 | 1994-01-13 | Bayer Ag | Kautschukmischungen enthaltend Polybutadien-Gel |
JPH0980752A (ja) * | 1995-09-18 | 1997-03-28 | Japan Synthetic Rubber Co Ltd | 水現像性感光性樹脂組成物 |
US5672639A (en) | 1996-03-12 | 1997-09-30 | The Goodyear Tire & Rubber Company | Starch composite reinforced rubber composition and tire with at least one component thereof |
DE19701488A1 (de) | 1997-01-17 | 1998-07-23 | Bayer Ag | SBR-Kautschukgele enthaltende Kautschukmischungen |
ATE239737T1 (de) | 1997-08-21 | 2003-05-15 | Crompton Corp | Blockierte merkaptosilane als kupplungsmittel für gefüllte kautschukzusammensetzung |
DE19834802A1 (de) | 1998-08-01 | 2000-02-03 | Continental Ag | Kautschukmischung |
DE19834804A1 (de) | 1998-08-01 | 2000-02-03 | Continental Ag | Kautschukmischung |
DE19834803A1 (de) | 1998-08-01 | 2000-02-03 | Continental Ag | Kautschukmischung |
US6344538B1 (en) * | 1998-08-24 | 2002-02-05 | Iowa State University Research Foundation, Inc. | Functionalized diene monomers and polymers containing functionalized dienes and methods for their preparation |
DE19942620A1 (de) | 1999-09-07 | 2001-03-08 | Bayer Ag | Mikrogelhaltige Kautschukmischungen mit verkappten bifunktionellen Mercaptanen und hieraus hergestellte Vulkanisate |
KR100344230B1 (ko) * | 1999-10-13 | 2002-07-24 | 금호석유화학 주식회사 | 산소분자를 이용한 하이드록시 고 1,4-시스 폴리부타디엔의 제조방법 |
JP3357325B2 (ja) * | 1999-11-01 | 2002-12-16 | 株式会社クラレ | 反応性オレフィン系重合体 |
DE60041550D1 (de) * | 1999-11-12 | 2009-03-26 | Bridgestone Corp | Modifizierte polymere hergestellt mit katalysator auf basys von lanthaniden |
US6627721B1 (en) | 2002-09-19 | 2003-09-30 | The Goodyear Tire & Rubber Company | Functionalized elastomers |
US6627722B2 (en) * | 2000-12-05 | 2003-09-30 | Stephan Rodewald | Functionalized elastomers |
ATE311396T1 (de) | 2001-08-06 | 2005-12-15 | Degussa | Organosiliciumverbindungen |
CA2433042A1 (en) | 2001-11-16 | 2003-05-30 | E.I. Du Pont De Nemours And Company | Copolymers of olefins and vinyl- and allylsilanes |
ES2200698B1 (es) | 2002-07-10 | 2005-06-01 | Consejo Sup. Investig. Cientificas | Catalizador para la polimerizacion de estireno y dienos, procedimiento de preparacion y utilizacion. |
US6933358B2 (en) * | 2002-08-16 | 2005-08-23 | The Goodyear Tire & Rubber Company | Functionalized monomers for synthesis of rubbery polymers |
US6693160B1 (en) * | 2002-08-16 | 2004-02-17 | The Goodyear Tire & Rubber Company | Functionalized monomers for synthesis of rubbery polymers |
US6753447B2 (en) * | 2002-08-16 | 2004-06-22 | The Goodyear Tire & Rubber Company | Functionalized monomers for synthesis of rubbery polymers |
JP4117834B2 (ja) * | 2002-12-20 | 2008-07-16 | 電気化学工業株式会社 | 4−メチレン−5−ヘキセニルトリアルコキシシラン及びその製造方法 |
JP4342800B2 (ja) * | 2003-01-07 | 2009-10-14 | 電気化学工業株式会社 | ポリクロロプレン系ゴム組成物及びその架橋成形物 |
JP4651921B2 (ja) * | 2003-07-17 | 2011-03-16 | 株式会社ブリヂストン | 空気入りタイヤ |
US8063152B2 (en) * | 2008-03-17 | 2011-11-22 | The Goodyear Tire & Rubber Company | Boron containing functionalizing agent |
SG155870A1 (en) * | 2008-03-31 | 2009-10-29 | Sumitomo Chemical Co | Conjugated diene polymer, process for producing same, and conjugated diene polymer composition and vulcanizate |
KR101152672B1 (ko) | 2009-11-30 | 2012-06-15 | 금호석유화학 주식회사 | 친수성 티오 에테르기로 말단변성된 스티렌-부타디엔 공중합체 및 이의 실리카 복합재 |
US8859687B2 (en) | 2011-12-21 | 2014-10-14 | The Goodyear Tire & Rubber Company | Functiontionalized elastomer |
EP2607381B1 (en) * | 2011-12-21 | 2018-01-24 | The Goodyear Tire & Rubber Company | Functionalized elastomer, rubber composition and tire |
JP5768788B2 (ja) * | 2012-09-21 | 2015-08-26 | 信越化学工業株式会社 | レジスト保護膜材料及びパターン形成方法 |
SG2013072061A (en) | 2012-09-26 | 2014-04-28 | Sumitomo Chemical Co | Method for producing modified conjugated diene-based polymer, and method for producing polymer composition |
CN102942656B (zh) * | 2012-10-31 | 2014-06-25 | 大连理工大学 | 含氮功能化稀土异戊橡胶及其制备方法 |
US8598286B1 (en) * | 2012-11-05 | 2013-12-03 | The Goodyear Tire & Rubber Company | High cis diene/phenylbutadiene copolymers prepared using a Ziegler/Natta neodymium catalyst |
JPWO2014088092A1 (ja) * | 2012-12-06 | 2017-01-05 | 横浜ゴム株式会社 | ジエン系ゴム組成物 |
CN104098744B (zh) | 2013-04-09 | 2018-02-16 | 住友化学株式会社 | 共轭二烯系聚合物,和含有该聚合物的聚合物组合物 |
JP2014227458A (ja) * | 2013-05-21 | 2014-12-08 | 株式会社ブリヂストン | 変性剤及びその変性剤を用いた変性共役ジエン系重合体、並びにその変性共役ジエン系重合体の製造方法 |
US9574024B1 (en) * | 2016-07-12 | 2017-02-21 | The Goodyear Tire & Rubber Company | Method of making a functionalized elastomer via allylboration |
US9580532B1 (en) * | 2016-07-12 | 2017-02-28 | The Goodyear Tire & Rubber Company | Functionalized elastomer via allylboration |
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US20160177008A1 (en) | 2016-06-23 |
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JP2017160413A (ja) | 2017-09-14 |
CN106905484B (zh) | 2019-05-21 |
CN105713137A (zh) | 2016-06-29 |
BR102016029677A2 (pt) | 2017-06-27 |
JP6795963B2 (ja) | 2020-12-02 |
CN106905485B (zh) | 2019-06-25 |
CN107011486A (zh) | 2017-08-04 |
US9969831B2 (en) | 2018-05-15 |
US9994663B2 (en) | 2018-06-12 |
JP2017149934A (ja) | 2017-08-31 |
US20160177009A1 (en) | 2016-06-23 |
BR102016028549A2 (pt) | 2017-06-27 |
EP3042786A1 (en) | 2016-07-13 |
CN107011486B (zh) | 2020-01-14 |
JP2017160412A (ja) | 2017-09-14 |
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