TWI607026B - Modified conjugated diene polymer, process for producing the same, and modified conjugated diene polymer composition - Google Patents
Modified conjugated diene polymer, process for producing the same, and modified conjugated diene polymer composition Download PDFInfo
- Publication number
- TWI607026B TWI607026B TW105105015A TW105105015A TWI607026B TW I607026 B TWI607026 B TW I607026B TW 105105015 A TW105105015 A TW 105105015A TW 105105015 A TW105105015 A TW 105105015A TW I607026 B TWI607026 B TW I607026B
- Authority
- TW
- Taiwan
- Prior art keywords
- conjugated diene
- carbon atoms
- group
- diene polymer
- modified conjugated
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims description 303
- 150000001993 dienes Chemical class 0.000 title claims description 255
- 238000000034 method Methods 0.000 title claims description 84
- 239000000203 mixture Substances 0.000 title claims description 64
- 230000008569 process Effects 0.000 title description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 186
- -1 diene compound Chemical class 0.000 claims description 133
- 229910052757 nitrogen Inorganic materials 0.000 claims description 99
- 125000000217 alkyl group Chemical group 0.000 claims description 91
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 85
- 238000006116 polymerization reaction Methods 0.000 claims description 85
- 229920001971 elastomer Polymers 0.000 claims description 81
- 239000005060 rubber Substances 0.000 claims description 69
- 150000002900 organolithium compounds Chemical class 0.000 claims description 65
- 229910052744 lithium Inorganic materials 0.000 claims description 62
- 150000001875 compounds Chemical class 0.000 claims description 54
- 239000002904 solvent Substances 0.000 claims description 49
- 239000003607 modifier Substances 0.000 claims description 48
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 43
- 229920002554 vinyl polymer Polymers 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 239000011256 inorganic filler Substances 0.000 claims description 36
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 36
- 125000002947 alkylene group Chemical group 0.000 claims description 35
- 238000004519 manufacturing process Methods 0.000 claims description 34
- 150000002430 hydrocarbons Chemical group 0.000 claims description 33
- 125000004122 cyclic group Chemical group 0.000 claims description 30
- 239000004215 Carbon black (E152) Substances 0.000 claims description 27
- 239000003795 chemical substances by application Substances 0.000 claims description 27
- 229930195733 hydrocarbon Natural products 0.000 claims description 27
- 230000004048 modification Effects 0.000 claims description 27
- 238000012986 modification Methods 0.000 claims description 27
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 26
- 238000005227 gel permeation chromatography Methods 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Chemical group CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 24
- 125000000524 functional group Chemical group 0.000 claims description 21
- 238000000149 argon plasma sintering Methods 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 19
- 239000000178 monomer Substances 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 claims description 10
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 230000000379 polymerizing effect Effects 0.000 claims description 9
- 238000007334 copolymerization reaction Methods 0.000 claims description 5
- 125000001302 tertiary amino group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 3
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical group CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 239000000523 sample Substances 0.000 description 90
- 229910000420 cerium oxide Inorganic materials 0.000 description 47
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 47
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 36
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 32
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 32
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 29
- 238000005259 measurement Methods 0.000 description 29
- 230000000704 physical effect Effects 0.000 description 29
- 239000003505 polymerization initiator Substances 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 28
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 25
- 229920001577 copolymer Polymers 0.000 description 25
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 21
- 238000004073 vulcanization Methods 0.000 description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
- 239000003921 oil Substances 0.000 description 16
- 241001441571 Hiodontidae Species 0.000 description 15
- 239000004793 Polystyrene Substances 0.000 description 15
- 238000005984 hydrogenation reaction Methods 0.000 description 15
- 238000004898 kneading Methods 0.000 description 15
- 229920002223 polystyrene Polymers 0.000 description 15
- 238000006276 transfer reaction Methods 0.000 description 15
- 238000002407 reforming Methods 0.000 description 13
- 239000006229 carbon black Substances 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000005299 abrasion Methods 0.000 description 11
- 239000012535 impurity Substances 0.000 description 11
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 11
- 238000002156 mixing Methods 0.000 description 11
- 230000009257 reactivity Effects 0.000 description 11
- JLZJTHTZQYTEMJ-UHFFFAOYSA-N 6,6-dimethylundecane-4,8-dione Chemical compound O=C(CC(C)(C)CC(CCC)=O)CCC JLZJTHTZQYTEMJ-UHFFFAOYSA-N 0.000 description 10
- 229920001400 block copolymer Polymers 0.000 description 10
- 230000007423 decrease Effects 0.000 description 10
- 229920003244 diene elastomer Polymers 0.000 description 10
- 239000000945 filler Substances 0.000 description 10
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000007822 coupling agent Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000000499 gel Substances 0.000 description 9
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- 230000003993 interaction Effects 0.000 description 9
- 229920005604 random copolymer Polymers 0.000 description 9
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000012545 processing Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 239000000446 fuel Substances 0.000 description 7
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 7
- 230000003068 static effect Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000004606 Fillers/Extenders Substances 0.000 description 6
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 6
- 150000004678 hydrides Chemical class 0.000 description 6
- 230000001976 improved effect Effects 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 239000011259 mixed solution Substances 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
- GRUPMVYXIWKMKX-UHFFFAOYSA-N COC(CCCCCCCCCCCCN(CCCCCCCCCCCCC(OC)(OC)OC)CCCCCCCCCCCCC(OC)(OC)OC)(OC)OC Chemical compound COC(CCCCCCCCCCCCN(CCCCCCCCCCCCC(OC)(OC)OC)CCCCCCCCCCCCC(OC)(OC)OC)(OC)OC GRUPMVYXIWKMKX-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 229910002090 carbon oxide Inorganic materials 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000001179 sorption measurement Methods 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- XQOHGUZOLKLXLU-NSCUHMNNSA-N 1-[(e)-but-2-enyl]piperidine Chemical compound C\C=C\CN1CCCCC1 XQOHGUZOLKLXLU-NSCUHMNNSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 235000021355 Stearic acid Nutrition 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000003712 anti-aging effect Effects 0.000 description 4
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 4
- 150000002642 lithium compounds Chemical class 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000008117 stearic acid Substances 0.000 description 4
- 239000001993 wax Substances 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- 235000014692 zinc oxide Nutrition 0.000 description 4
- NIDSRGCVYOEDFW-UHFFFAOYSA-N 1-bromo-4-chlorobutane Chemical compound ClCCCCBr NIDSRGCVYOEDFW-UHFFFAOYSA-N 0.000 description 3
- JTYUIAOHIYZBPB-UHFFFAOYSA-N 1-bromo-6-chlorohexane Chemical compound ClCCCCCCBr JTYUIAOHIYZBPB-UHFFFAOYSA-N 0.000 description 3
- LQSLIVBRDRMOPF-UHFFFAOYSA-N 1-but-2-enylazepane Chemical compound CC=CCN1CCCCCC1 LQSLIVBRDRMOPF-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- 239000006236 Super Abrasion Furnace Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- OQWGPAUHCNJJML-UHFFFAOYSA-N [Li]CCCN1CCCCC1 Chemical compound [Li]CCCN1CCCCC1 OQWGPAUHCNJJML-UHFFFAOYSA-N 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 150000001339 alkali metal compounds Chemical class 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- 150000004292 cyclic ethers Chemical class 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000006011 modification reaction Methods 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 150000002902 organometallic compounds Chemical class 0.000 description 3
- 125000003544 oxime group Chemical group 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- HBOZHTSTTRVJNT-UHFFFAOYSA-N 1-(3-chloropropyl)azepane Chemical compound ClCCCN1CCCCCC1 HBOZHTSTTRVJNT-UHFFFAOYSA-N 0.000 description 2
- AMJBCNIDVLQCBR-UHFFFAOYSA-N 1-bromo-10-chlorodecane Chemical compound ClCCCCCCCCCCBr AMJBCNIDVLQCBR-UHFFFAOYSA-N 0.000 description 2
- PHHNNDKXQVKJEP-UHFFFAOYSA-N 1-bromo-5-chloropentane Chemical compound ClCCCCCBr PHHNNDKXQVKJEP-UHFFFAOYSA-N 0.000 description 2
- YEXRJDRHGBFDDA-UHFFFAOYSA-N 1-chloropentan-3-amine Chemical compound CCC(N)CCCl YEXRJDRHGBFDDA-UHFFFAOYSA-N 0.000 description 2
- FRAKHUZTNLUGPB-UHFFFAOYSA-N 3,3,5-trimethyl-7-azabicyclo[3.2.1]octane Chemical compound C1C2NCC1(C)CC(C)(C)C2 FRAKHUZTNLUGPB-UHFFFAOYSA-N 0.000 description 2
- IDWRJRPUIXRFRX-UHFFFAOYSA-N 3,5-dimethylpiperidine Chemical compound CC1CNCC(C)C1 IDWRJRPUIXRFRX-UHFFFAOYSA-N 0.000 description 2
- GWDKGEXAGYTRFW-UHFFFAOYSA-N 5-(2-chloroethyl)nonan-5-amine Chemical compound CCCCC(N)(CCCl)CCCC GWDKGEXAGYTRFW-UHFFFAOYSA-N 0.000 description 2
- JIGKHPDEYQTSEM-UHFFFAOYSA-N C(C)OC(CCCCCCCCCCCCN(CCCCCCCCCCCCC(OCC)(OCC)OCC)CCCCCCCCCCCCC(OCC)(OCC)OCC)(OCC)OCC Chemical compound C(C)OC(CCCCCCCCCCCCN(CCCCCCCCCCCCC(OCC)(OCC)OCC)CCCCCCCCCCCCC(OCC)(OCC)OCC)(OCC)OCC JIGKHPDEYQTSEM-UHFFFAOYSA-N 0.000 description 2
- SZVYBVKQCKAKOY-UHFFFAOYSA-N C1CCCCCCC1.[N] Chemical compound C1CCCCCCC1.[N] SZVYBVKQCKAKOY-UHFFFAOYSA-N 0.000 description 2
- JPZDHMXFYZKTLI-UHFFFAOYSA-N C1CCCCCCC1.[N].[Li] Chemical compound C1CCCCCCC1.[N].[Li] JPZDHMXFYZKTLI-UHFFFAOYSA-N 0.000 description 2
- ATDCCNMSIUEZKJ-UHFFFAOYSA-N CCCC(CCCCCCCCCC(OCC)OCC)N(C(CCC)CCCCCCCCCC(OCC)OCC)C(CCC)CCCCCCCCCC(OCC)OCC Chemical compound CCCC(CCCCCCCCCC(OCC)OCC)N(C(CCC)CCCCCCCCCC(OCC)OCC)C(CCC)CCCCCCCCCC(OCC)OCC ATDCCNMSIUEZKJ-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
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 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
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 239000006240 Fast Extruding Furnace Substances 0.000 description 2
- 239000006238 High Abrasion Furnace Substances 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OUBMGJOQLXMSNT-UHFFFAOYSA-N N-isopropyl-N'-phenyl-p-phenylenediamine Chemical compound C1=CC(NC(C)C)=CC=C1NC1=CC=CC=C1 OUBMGJOQLXMSNT-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000006242 Semi-Reinforcing Furnace Substances 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- GRORYRKNHPLGCF-UHFFFAOYSA-N [Li].CN(C)c1ccccc1C Chemical compound [Li].CN(C)c1ccccc1C GRORYRKNHPLGCF-UHFFFAOYSA-N 0.000 description 2
- LTVDQDKMLGXKGD-UHFFFAOYSA-N [Li].N[Li] Chemical compound [Li].N[Li] LTVDQDKMLGXKGD-UHFFFAOYSA-N 0.000 description 2
- ANGAPPADVYSUPS-UHFFFAOYSA-N [Li]CCCN1CCC=CC1 Chemical compound [Li]CCCN1CCC=CC1 ANGAPPADVYSUPS-UHFFFAOYSA-N 0.000 description 2
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000010692 aromatic oil Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical group CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
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- 238000000746 purification Methods 0.000 description 1
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- 238000011002 quantification Methods 0.000 description 1
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- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
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- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
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- 229910052723 transition metal Inorganic materials 0.000 description 1
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- 230000004580 weight loss Effects 0.000 description 1
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Classifications
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- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/25—Incorporating silicon atoms into the molecule
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/06—Butadiene
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
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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
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- 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
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- 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
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- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
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- 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
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/544—Silicon-containing compounds containing nitrogen
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- 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
- C08K5/00—Use of organic ingredients
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- C08K5/544—Silicon-containing compounds containing nitrogen
- C08K5/5445—Silicon-containing compounds containing nitrogen containing at least one Si-N bond
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- 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
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- C08K5/5477—Silicon-containing compounds containing nitrogen containing nitrogen in a heterocyclic ring
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L47/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Compositions of derivatives of such polymers
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L9/06—Copolymers with styrene
Landscapes
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
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- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerization Catalysts (AREA)
- Tires In General (AREA)
Applications Claiming Priority (1)
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| JP2015031082 | 2015-02-19 |
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| EP3345933A4 (en) * | 2015-08-31 | 2018-09-05 | Bridgestone Corporation | Method for producing modified diene rubber, rubber composition, and tire |
| KR102143416B1 (ko) * | 2016-08-19 | 2020-08-11 | 아사히 가세이 가부시키가이샤 | 변성 공액 디엔계 중합체, 그의 제조 방법, 고무 조성물, 타이어 |
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| JP2018123225A (ja) * | 2017-01-31 | 2018-08-09 | 旭化成株式会社 | ヒステリシスロスが改良されたゴム組成物、加硫物、及びゴム組成物の製造方法 |
| US11292862B2 (en) * | 2017-03-07 | 2022-04-05 | Asahi Kasei Kabushiki Kaisha | Modified conjugated diene-based polymer, polymer composition, and rubber composition |
| EP3617237B1 (en) | 2017-04-28 | 2021-08-25 | Asahi Kasei Kabushiki Kaisha | Modified conjugated diene polymer, polymer composition, and rubber composition |
| CN110740845B (zh) * | 2017-07-06 | 2021-08-27 | 三菱重工机械系统株式会社 | 混炼机控制装置、混炼机控制方法及程序 |
| KR102328792B1 (ko) * | 2017-09-18 | 2021-11-22 | 주식회사 엘지화학 | 연속식 중합에 의한 공액디엔계 중합체의 제조방법 |
| KR102167122B1 (ko) | 2017-12-05 | 2020-10-16 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
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| KR102323810B1 (ko) * | 2017-12-05 | 2021-11-10 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
| WO2019112261A1 (ko) * | 2017-12-05 | 2019-06-13 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
| KR102122471B1 (ko) * | 2017-12-05 | 2020-06-26 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
| KR102179487B1 (ko) * | 2017-12-05 | 2020-11-16 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
| KR102288852B1 (ko) * | 2018-05-25 | 2021-08-12 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
| WO2019225824A1 (ko) * | 2018-05-25 | 2019-11-28 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
| JP7280115B2 (ja) * | 2018-06-28 | 2023-05-23 | 旭化成株式会社 | 変性共役ジエン系重合体混合物の製造方法 |
| CN110684154B (zh) * | 2018-07-04 | 2022-05-17 | 旭化成株式会社 | 改性共轭二烯系聚合物、改性共轭二烯系聚合物组合物以及橡胶组合物 |
| KR102035177B1 (ko) * | 2018-07-11 | 2019-11-08 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
| JP7161883B2 (ja) * | 2018-07-27 | 2022-10-27 | 旭化成株式会社 | 変性共役ジエン系重合体、その製造方法、変性共役ジエン系組成物、及びタイヤ |
| JP7385394B2 (ja) * | 2018-08-30 | 2023-11-22 | 旭化成株式会社 | 変性共役ジエン系重合体組成物、ゴム組成物、ゴム組成物の製造方法、及びタイヤ |
| JP7574179B2 (ja) * | 2018-09-03 | 2024-10-28 | シントス エス．アー． | アミノシリル官能化共役ジエン、その調製、およびゴムの製造におけるその使用方法 |
| WO2020071557A1 (ja) * | 2018-10-04 | 2020-04-09 | 株式会社ブリヂストン | ゴム組成物、トレッドゴムおよびタイヤ |
| EP4026704B1 (en) * | 2019-09-05 | 2024-09-04 | Asahi Kasei Kabushiki Kaisha | Conjugated diene polymer, method for producing conjugated diene polymer, conjugated diene polymer composition, and rubber composition |
| KR102533014B1 (ko) | 2019-09-11 | 2023-05-17 | 주식회사 엘지화학 | 변성 공액디엔계 중합체, 이의 제조방법 및 이를 포함하는 고무 조성물 |
| TW202122426A (zh) | 2019-09-11 | 2021-06-16 | 南韓商Ｌｇ化學股份有限公司 | 改質之共軛二烯系聚合物、其製備方法及包含彼之橡膠組成物 |
| JP7280972B2 (ja) | 2019-09-11 | 2023-05-24 | エルジー・ケム・リミテッド | 変性共役ジエン系重合体、その製造方法、およびそれを含むゴム組成物 |
| KR102800784B1 (ko) * | 2019-09-27 | 2025-04-29 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
| TW202128798A (zh) * | 2019-09-30 | 2021-08-01 | 南韓商Ｌｇ化學股份有限公司 | 經改質之以共軛二烯為底的聚合物、其製備方法及含彼的橡膠組成物 |
| WO2021085829A1 (ko) * | 2019-10-30 | 2021-05-06 | 주식회사 엘지화학 | 변성 공액디엔계 중합체 및 이를 포함하는 고무 조성물 |
| WO2021187270A1 (ja) * | 2020-03-17 | 2021-09-23 | Jsr株式会社 | 全固体二次電池用バインダー、全固体二次電池用バインダー組成物、全固体二次電池用スラリー、全固体二次電池用固体電解質シート及びその製造方法、並びに全固体二次電池及びその製造方法 |
| JP7526270B2 (ja) | 2020-08-11 | 2024-07-31 | 旭化成株式会社 | 包装成形体、架橋用ゴム組成物、包装成形体の製造方法、架橋用ゴム組成物の製造方法、及びタイヤ用トレッド |
| CN118215687A (zh) | 2021-12-07 | 2024-06-18 | 阿朗新科德国有限责任公司 | 用不饱和的基于硅氧烷的偶联剂制备的官能化二烯橡胶 |
| EP4570827A4 (en) * | 2022-08-12 | 2025-11-26 | Asahi Chemical Ind | Conjugated diene polymer, molded body, process for producing conjugated diene polymer, rubber and tire composition |
| JP7581541B2 (ja) * | 2022-08-24 | 2024-11-12 | 旭化成株式会社 | ゴム改質用マスターバッチ、及び分岐共役ジエン系重合体組成物 |
| WO2025150432A1 (ja) * | 2024-01-12 | 2025-07-17 | 旭化成株式会社 | 変性共役ジエン系重合体、及び変性共役ジエン系重合体の製造方法 |
| WO2025181638A1 (en) | 2024-02-26 | 2025-09-04 | Versalis S.P.A. | Functionalized styrene-butadiene random copolymers and process for the preparation thereof |
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| TW201204746A (en) * | 2010-04-16 | 2012-02-01 | Asahi Kasei Chemicals Corp | Process for producing modified conjugated diene polymer, modified conjugated diene polymer, and composition of modified conjugated diene polymer |
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| JP3441201B2 (ja) | 1993-12-29 | 2003-08-25 | 株式会社ブリヂストン | 重合体及びその重合体組成物 |
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| JP5576020B2 (ja) * | 2005-09-22 | 2014-08-20 | 旭化成ケミカルズ株式会社 | 共役ジエン系重合体およびその製造方法 |
| JP5568860B2 (ja) | 2006-03-31 | 2014-08-13 | 日本ゼオン株式会社 | タイヤ用ゴム組成物の製造方法、タイヤ用ゴム組成物、及びタイヤ |
| JP5127521B2 (ja) * | 2008-03-24 | 2013-01-23 | 旭化成ケミカルズ株式会社 | 変性共役ジエン系重合体及びその製造方法、並びに重合体組成物 |
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| JP5964571B2 (ja) * | 2011-10-12 | 2016-08-03 | 旭化成株式会社 | 変性共役ジエン系重合体の製造方法、変性共役ジエン系重合体、及び変性共役ジエン系重合体組成物、及びタイヤ |
| JP6032882B2 (ja) * | 2011-10-19 | 2016-11-30 | 旭化成株式会社 | サイドウォール用ゴム組成物 |
| JP2013129693A (ja) | 2011-12-20 | 2013-07-04 | Asahi Kasei Chemicals Corp | 変性共役ジエン重合体の製造方法及び変性共役ジエン重合体の組成物 |
| JP6106476B2 (ja) * | 2013-03-13 | 2017-03-29 | 旭化成株式会社 | 変性共役ジエン系重合体組成物、トレッド、サイドウォール及びタイヤ |
| JP2015113437A (ja) * | 2013-12-13 | 2015-06-22 | 旭化成ケミカルズ株式会社 | 変性共役ジエン系重合体組成物の製造方法 |
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| TW201204746A (en) * | 2010-04-16 | 2012-02-01 | Asahi Kasei Chemicals Corp | Process for producing modified conjugated diene polymer, modified conjugated diene polymer, and composition of modified conjugated diene polymer |
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|---|---|
| EP3260476A1 (en) | 2017-12-27 |
| JP6908662B2 (ja) | 2021-07-28 |
| TW201708272A (zh) | 2017-03-01 |
| KR20190060893A (ko) | 2019-06-03 |
| JP2019206723A (ja) | 2019-12-05 |
| CN107250172B (zh) | 2021-04-09 |
| HUE044416T2 (hu) | 2019-10-28 |
| EP3260476B1 (en) | 2019-05-08 |
| WO2016133202A1 (ja) | 2016-08-25 |
| BR112017016522A2 (pt) | 2018-04-10 |
| KR102160548B9 (ko) | 2022-02-18 |
| US20180037674A1 (en) | 2018-02-08 |
| JPWO2016133202A1 (ja) | 2017-11-02 |
| KR102160548B1 (ko) | 2020-09-28 |
| KR20170102320A (ko) | 2017-09-08 |
| JP6607916B2 (ja) | 2019-11-20 |
| SG11201706426YA (en) | 2017-09-28 |
| CN107250172A (zh) | 2017-10-13 |
| EP3260476A4 (en) | 2018-01-03 |
| US10766972B2 (en) | 2020-09-08 |
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