WO2021049906A1 - Modified conjugated diene-based polymer, method for producing same, and rubber composition comprising same - Google Patents
Modified conjugated diene-based polymer, method for producing same, and rubber composition comprising same Download PDFInfo
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- WO2021049906A1 WO2021049906A1 PCT/KR2020/012312 KR2020012312W WO2021049906A1 WO 2021049906 A1 WO2021049906 A1 WO 2021049906A1 KR 2020012312 W KR2020012312 W KR 2020012312W WO 2021049906 A1 WO2021049906 A1 WO 2021049906A1
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- WO
- WIPO (PCT)
- Prior art keywords
- carbon atoms
- group
- conjugated diene
- formula
- substituent
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract description 163
- 150000001993 dienes Chemical class 0.000 title claims abstract description 116
- 229920001971 elastomer Polymers 0.000 title claims abstract description 64
- 239000005060 rubber Substances 0.000 title claims abstract description 64
- 239000000203 mixture Substances 0.000 title claims abstract description 38
- 238000004519 manufacturing process Methods 0.000 title claims description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 75
- 239000003607 modifier Substances 0.000 claims abstract description 63
- 239000000178 monomer Substances 0.000 claims abstract description 58
- 125000004432 carbon atom Chemical group C* 0.000 claims description 298
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 125000001424 substituent group Chemical group 0.000 claims description 58
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- 229920002554 vinyl polymer Polymers 0.000 claims description 26
- 125000002947 alkylene group Chemical group 0.000 claims description 25
- 239000003398 denaturant Substances 0.000 claims description 24
- 238000006116 polymerization reaction Methods 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 125000000304 alkynyl group Chemical group 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 22
- 239000000945 filler Substances 0.000 claims description 21
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 16
- 239000003505 polymerization initiator Substances 0.000 claims description 16
- 150000002430 hydrocarbons Chemical class 0.000 claims description 13
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 12
- 125000000732 arylene group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 239000004215 Carbon black (E152) Substances 0.000 claims description 10
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000006735 (C1-C20) heteroalkyl group Chemical group 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 5
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 3
- 150000002900 organolithium compounds Chemical class 0.000 claims description 3
- -1 alkoxy silane Chemical compound 0.000 abstract description 23
- 239000000126 substance Substances 0.000 abstract description 11
- 229910000077 silane Inorganic materials 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 50
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 36
- 125000000524 functional group Chemical group 0.000 description 34
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 34
- 229920003048 styrene butadiene rubber Polymers 0.000 description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 29
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 25
- 230000000694 effects Effects 0.000 description 22
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 125000003545 alkoxy group Chemical group 0.000 description 18
- 239000003795 chemical substances by application Substances 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 239000000377 silicon dioxide Substances 0.000 description 15
- 125000004429 atom Chemical group 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 239000000654 additive Substances 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 11
- 238000009826 distribution Methods 0.000 description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 11
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- 244000043261 Hevea brasiliensis Species 0.000 description 9
- 229920003052 natural elastomer Polymers 0.000 description 9
- 229920001194 natural rubber Polymers 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 8
- 239000002174 Styrene-butadiene Substances 0.000 description 7
- 239000003963 antioxidant agent Substances 0.000 description 7
- 230000003078 antioxidant effect Effects 0.000 description 7
- 230000008859 change Effects 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 230000001965 increasing effect Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 6
- 238000004925 denaturation Methods 0.000 description 6
- 230000036425 denaturation Effects 0.000 description 6
- 238000009616 inductively coupled plasma Methods 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 239000010734 process oil Substances 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 6
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000005062 Polybutadiene Substances 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000000446 fuel Substances 0.000 description 5
- 238000004898 kneading Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000001294 propane Substances 0.000 description 5
- 238000005096 rolling process Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 239000006087 Silane Coupling Agent Substances 0.000 description 4
- 238000005299 abrasion Methods 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 238000011088 calibration curve Methods 0.000 description 4
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 4
- 230000020169 heat generation Effects 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- XOAJIYVOSJHEQB-UHFFFAOYSA-N trimethyl trimethoxysilyl silicate Chemical compound CO[Si](OC)(OC)O[Si](OC)(OC)OC XOAJIYVOSJHEQB-UHFFFAOYSA-N 0.000 description 4
- 238000004073 vulcanization Methods 0.000 description 4
- 239000004636 vulcanized rubber Substances 0.000 description 4
- KHLWLJFRUQJJKQ-UHFFFAOYSA-N 3-trimethoxysilyl-n,n-bis(3-trimethoxysilylpropyl)propan-1-amine Chemical compound CO[Si](OC)(OC)CCCN(CCC[Si](OC)(OC)OC)CCC[Si](OC)(OC)OC KHLWLJFRUQJJKQ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 0 CC(*)=C(*)*c1ccccc1 Chemical compound CC(*)=C(*)*c1ccccc1 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 230000003712 anti-aging effect Effects 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- PQZTVWVYCLIIJY-UHFFFAOYSA-N diethyl(propyl)amine Chemical compound CCCN(CC)CC PQZTVWVYCLIIJY-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 238000006011 modification reaction Methods 0.000 description 3
- UVBMZKBIZUWTLV-UHFFFAOYSA-N n-methyl-n-propylpropan-1-amine Chemical compound CCCN(C)CCC UVBMZKBIZUWTLV-UHFFFAOYSA-N 0.000 description 3
- IPJPAQIHUIKFLV-UHFFFAOYSA-N n-trimethylsilylaniline Chemical compound C[Si](C)(C)NC1=CC=CC=C1 IPJPAQIHUIKFLV-UHFFFAOYSA-N 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 3
- 229920005604 random copolymer Polymers 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-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
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- VUFKMYLDDDNUJS-UHFFFAOYSA-N 2-(ethoxymethyl)oxolane Chemical compound CCOCC1CCCO1 VUFKMYLDDDNUJS-UHFFFAOYSA-N 0.000 description 2
- ZMRPAKWTPKQKIG-UHFFFAOYSA-N 3-[[3-(dipropylamino)propyl-diethoxysilyl]oxy-diethoxysilyl]-N,N-dipropylpropan-1-amine Chemical compound C(C)O[Si](O[Si](OCC)(OCC)CCCN(CCC)CCC)(OCC)CCCN(CCC)CCC ZMRPAKWTPKQKIG-UHFFFAOYSA-N 0.000 description 2
- XHQGVGCNYIYYEE-UHFFFAOYSA-N 3-imidazol-1-ylpropyl-[3-imidazol-1-ylpropyl(dipropoxy)silyl]oxy-dipropoxysilane Chemical compound N1(C=NC=C1)CCC[Si](O[Si](OCCC)(OCCC)CCCN1C=NC=C1)(OCCC)OCCC XHQGVGCNYIYYEE-UHFFFAOYSA-N 0.000 description 2
- BIGOJJYDFLNSGB-UHFFFAOYSA-N 3-isocyanopropyl(trimethoxy)silane Chemical group CO[Si](OC)(OC)CCC[N+]#[C-] BIGOJJYDFLNSGB-UHFFFAOYSA-N 0.000 description 2
- GQWAOUOHRMHSHL-UHFFFAOYSA-N 4-ethenyl-n,n-dimethylaniline Chemical compound CN(C)C1=CC=C(C=C)C=C1 GQWAOUOHRMHSHL-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- ZATOFRITFRPYBT-UHFFFAOYSA-N C1=CC=C2C([Li])=CC=CC2=C1 Chemical compound C1=CC=C2C([Li])=CC=CC2=C1 ZATOFRITFRPYBT-UHFFFAOYSA-N 0.000 description 2
- XXKXZTMYBPAGIB-UHFFFAOYSA-N CO[Si](CCCN(CCC[Si](OC)(OC)OC)CCC[Si](OC)(OC)OC)(OC)OC.CO[Si](CCCN(CCC[Si](OC)(OC)OC)CCC[Si](OC)(OC)OC)(OC)OC Chemical compound CO[Si](CCCN(CCC[Si](OC)(OC)OC)CCC[Si](OC)(OC)OC)(OC)OC.CO[Si](CCCN(CCC[Si](OC)(OC)OC)CCC[Si](OC)(OC)OC)(OC)OC XXKXZTMYBPAGIB-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000005103 alkyl silyl group Chemical group 0.000 description 2
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 2
- 229920005549 butyl rubber Polymers 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 2
- CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 description 2
- SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 description 2
- XBEREOHJDYAKDA-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].CC[CH2-] XBEREOHJDYAKDA-UHFFFAOYSA-N 0.000 description 2
- 238000010551 living anionic polymerization reaction Methods 0.000 description 2
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- HQHSMYARHRXIDS-UHFFFAOYSA-N n,n-dimethyl-1-phenylprop-2-en-1-amine Chemical compound CN(C)C(C=C)C1=CC=CC=C1 HQHSMYARHRXIDS-UHFFFAOYSA-N 0.000 description 2
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 2
- 229920001195 polyisoprene Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000005077 polysulfide Substances 0.000 description 2
- 229920001021 polysulfide Polymers 0.000 description 2
- 150000008117 polysulfides Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000003014 reinforcing effect Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- HTMDLQGFGSQOLM-YMQJAAJZSA-N sodium (1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexan-1-olate Chemical compound [Na+].CC(C)[C@@H]1CC[C@@H](C)C[C@H]1[O-] HTMDLQGFGSQOLM-YMQJAAJZSA-N 0.000 description 2
- 239000010421 standard material Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- QLNOVKKVHFRGMA-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical group [CH2]CC[Si](OC)(OC)OC QLNOVKKVHFRGMA-UHFFFAOYSA-N 0.000 description 2
- 229910021642 ultra pure water Inorganic materials 0.000 description 2
- 239000012498 ultrapure water Substances 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
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- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 229920003211 cis-1,4-polyisoprene Polymers 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- PUJYFNMXCFLEDM-UHFFFAOYSA-N cyclopentane Chemical compound C1CC[CH+]C1 PUJYFNMXCFLEDM-UHFFFAOYSA-N 0.000 description 1
- BOTLEXFFFSMRLQ-UHFFFAOYSA-N cyclopentyloxycyclopentane Chemical compound C1CCCC1OC1CCCC1 BOTLEXFFFSMRLQ-UHFFFAOYSA-N 0.000 description 1
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 1
- GSYVJAOBRKCNOT-UHFFFAOYSA-N diethoxymethyl-[3-[3-(diethoxymethylsilyl)propyltetrasulfanyl]propyl]silane Chemical compound CCOC(OCC)[SiH2]CCCSSSSCCC[SiH2]C(OCC)OCC GSYVJAOBRKCNOT-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 229920005558 epichlorohydrin rubber Polymers 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 description 1
- 235000019285 ethoxyquin Nutrition 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- ZONYXWQDUYMKFB-UHFFFAOYSA-N flavanone Chemical compound O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 229920005555 halobutyl Polymers 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- NRUBUZBAZRTHHX-UHFFFAOYSA-N lithium;propan-2-ylazanide Chemical compound [Li+].CC(C)[NH-] NRUBUZBAZRTHHX-UHFFFAOYSA-N 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical compound CNCCN KFIGICHILYTCJF-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- ASAOXGWSIOQTDI-UHFFFAOYSA-N triethoxy-[2-(2-triethoxysilylethyltetrasulfanyl)ethyl]silane Chemical compound CCO[Si](OCC)(OCC)CCSSSSCC[Si](OCC)(OCC)OCC ASAOXGWSIOQTDI-UHFFFAOYSA-N 0.000 description 1
- FBBATURSCRIBHN-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSCCC[Si](OCC)(OCC)OCC FBBATURSCRIBHN-UHFFFAOYSA-N 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical group CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- KLFNHRIZTXWZHT-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltrisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSCCC[Si](OCC)(OCC)OCC KLFNHRIZTXWZHT-UHFFFAOYSA-N 0.000 description 1
- QKJGTZOWMVHEHS-UHFFFAOYSA-N triethoxy-[3-(phenyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSC1=CC=CC=C1 QKJGTZOWMVHEHS-UHFFFAOYSA-N 0.000 description 1
- JSXKIRYGYMKWSK-UHFFFAOYSA-N trimethoxy-[2-(2-trimethoxysilylethyltetrasulfanyl)ethyl]silane Chemical compound CO[Si](OC)(OC)CCSSSSCC[Si](OC)(OC)OC JSXKIRYGYMKWSK-UHFFFAOYSA-N 0.000 description 1
- UMKAXYIUADSMOD-UHFFFAOYSA-N trimethoxy-[3-trimethoxysilyl-2,2-bis(trimethoxysilylmethyl)propyl]silane Chemical compound CO[Si](OC)(OC)CC(C[Si](OC)(OC)OC)(C[Si](OC)(OC)OC)C[Si](OC)(OC)OC UMKAXYIUADSMOD-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- 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
-
- 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
- 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
- C08F236/10—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 with vinyl-aromatic monomers
-
- 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
- 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
- C08F236/14—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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/08—Epoxidation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/42—Introducing metal atoms or metal-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L15/00—Compositions of rubber derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
- C08L9/06—Copolymers with styrene
Definitions
- R 1a to R 1c are each independently a hydrogen atom; An alkyl group having 1 to 20 carbon atoms; An alkenyl group having 2 to 20 carbon atoms; An alkynyl group having 2 to 20 carbon atoms; A C1-C20 heteroalkyl group, a C2-C20 heteroalkenyl group; A heteroalkynyl group having 2 to 20 carbon atoms; A cycloalkyl group having 5 to 20 carbon atoms; Aryl group having 6 to 20 carbon atoms; Or a heterocyclic group having 3 to 20 carbon atoms,
- the term'aralkyl' is also called aralkyl and may mean a combination of an alkyl group and an aryl group formed by replacing a hydrogen atom bonded to a carbon constituting an alkyl group with an aryl group.
- the modified conjugated diene-based polymer according to an embodiment of the present invention includes a first chain including a repeating unit derived from a conjugated diene-based monomer; A second chain comprising a repeating unit derived from a compound represented by the following formula (1); And a unit derived from an alkoxysilane modifier, wherein the first chain and the second chain are coupled by a unit derived from the modifier.
- the modified conjugated diene-based polymer has a residue derived from a denaturant, such as an alkoxy group (-OR, where R is a hydrocarbon group) or a hydroxyl group (-OH), and condensation reaction or
- a denaturant such as an alkoxy group (-OR, where R is a hydrocarbon group) or a hydroxyl group (-OH)
- the storage stability decreases due to hydrolysis reaction, etc., resulting in an increase in Mooney viscosity and an increase in molecular weight distribution. Accordingly, the excellent properties of the blended properties of the modified conjugated diene-based polymer are not maintained. There is a problem that cannot be obtained.
- the modified conjugated diene-based polymer according to an embodiment of the present invention has the advantage of being able to introduce more functional groups than when only a modifier having a large number of functional groups is used by being prepared by a manufacturing method described below.
- the alkoxy group of the active polymer and the modifier is difficult to bind two or more polymer chains to one molecule of the modifier due to steric hindrance of the polymer, and although three or more chains may be bonded, a modified polymer in which three or more chains are coupled. Is bound to be a trace amount.
- the modified conjugated diene-based polymer according to an embodiment of the present invention further includes a second chain in addition to the first chain, and the second chain is from a macromonomer containing a repeating unit derived from a compound represented by Formula 1 As derived, the main unit may be a repeating unit derived from a compound represented by Formula 1.
- the compound represented by Formula 1 may be a compound represented by Formulas 1-1 to 1-3 below.
- the compound represented by Formula 2 may be one or more selected from compounds represented by the following Formulas 2-1 to 2-6.
- R 5 , R 6 and R 9 may each independently be an alkylene group having 1 to 10 carbon atoms
- R 7 , R 8 , R 10 and R 11 may each independently be an alkyl group having 1 to 10 carbon atoms
- R 12 may be hydrogen or an alkyl group having 1 to 10 carbon atoms
- b and c may each independently be 1, 2 or 3, b+c ⁇ 4, and A is or
- R 13 , R 14 , R 15 and R 16 may each independently be hydrogen or an alkyl group having 1 to 10 carbon atoms.
- the compound represented by Formula 3 is N-(3-(1H-imidazol-1-yl)propyl)-3-(triethoxysilyl)-N-(3-(triethoxysilyl)propyl Propan-1-amine (N-(3-(1H-imidazol-1-yl)propyl)-3-(triethoxysilyl)-N-(3-(triethoxysilyl)propyl)propan-1-amine) and 3-(4 ,5-dihydro-1H-imidazol-1-yl)-N,N-bis(3-(triethoxysilyl)propyl)propan-1-amine (3-(4,5-dihydro-1H-imidazol) It may be one selected from the group consisting of -1-yl)-N,N-bis(3-(triethoxysilyl)propyl)propan-1-amine).
- the compound represented by Formula 4 is 3,3'-(1,1,3,3-tetramethoxydisiloxane-1,3-diyl)bis(N,N-dimethylpropan-1-amine)( 3,3'-(1,1,3,3-tetramethoxydisiloxane-1,3-diyl)bis(N,N-dimethylpropan-1-amine), 3,3'-(1,1,3,3-tetra Ethoxydisiloxane-1,3-diyl)bis(N,N-dimethylpropan-1-amine)(3,3'-(1,1,3,3-tetraethoxydisiloxane-1,3-diyl)bis(N ,N-dimethylpropan-1-amine), 3,3'-(1,1,3,3-tetrapropoxydisiloxane-1,3-diyl)bis(N,N-dimethylpropan-1-amine)( 3,3'-(1,1,3,3-tetraprop
- the compound represented by Formula 4 may be a compound represented by Formula 4-1 below.
- Me is a methyl group.
- R b2 to R b4 are each independently an alkylene group having 1 to 10 carbon atoms
- R b5 to R b8 are each independently an alkyl group having 1 to 10 carbon atoms
- R b13 and R b14 are independently of each other It is an alkylene group of 1 to 10
- R b15 to R b18 are each independently an alkyl group having 1 to 10 carbon atoms
- m 1, m 2 , m 3 and m 4 are each independently an integer of 1 to 3.
- the amine-free alkoxysilane modifier may be a compound represented by Formula 8 below.
- the amine-free alkoxysilane modifier may be a compound represented by Formula 9 below.
- the content of N atoms in the polymer according to NSX analysis is 150 ppm or more by weight, and the content of Si atoms in the polymer according to ICP analysis is based on weight. It may be more than 180 ppm.
- the Mooney viscosity change rate may be an indicator that not only processability but also the increase in Mooney viscosity occurring during storage after manufacture is small.
- the polymer according to the present invention includes a repeating unit derived from a compound represented by Formula 1 Due to the structural characteristics in which the second chain, the denaturant-derived unit, and the first chain of the polymer are bonded to each other in a specific structure, the processability is improved, and even when stored for a long time, the change rate of Mooney viscosity is low, so storage stability can be excellent.
- the polymerization initiator is not particularly limited, for example, methyllithium, ethyllithium, propyllithium, isopropyllithium, n-butyllithium, s-butyllithium, t-butyllithium, hexyllithium, n-decyllithium, t-octyl Lithium, phenyllithium, 1-naphthyllithium, n-eicosyllithium, 4-butylphenyllithium, 4-tolyllithium, cyclohexyllithium, 3,5-di-n-heptylcyclohexyllithium, 4-cyclopentyllithium , Naphthyl sodium, naphthyl potassium, lithium alkoxide, sodium alkoxide, potassium alkoxide, lithium sulfonate, sodium sulfonate, potassium sulfonate, lithium amide, sodium amide, potassium amide and lithium is
- the polymerization in step (S1) may be an anionic polymerization as an example, and a specific example may be a living anionic polymerization having an anionic active site at the polymerization end by a growth polymerization reaction by an anion.
- the polymerization in step (S1) may be elevated temperature polymerization, isothermal polymerization, or constant temperature polymerization (insulation polymerization), and the constant temperature polymerization includes polymerization by self-reaction heat without optionally applying heat after the polymerization initiator is added.
- the elevated-temperature polymerization may mean a polymerization method in which heat is arbitrarily applied after the polymerization initiator is added to increase the temperature, and the isothermal polymerization is heated by applying heat after the polymerization initiator is added. It may mean a polymerization method in which the temperature of the polymerized product is kept constant by increasing or taking away heat.
- the step (S2) is a step for preparing a denatured active first chain by reacting the active first chain with a denaturant, wherein the reaction may be a denaturation or a coupling reaction, wherein the denaturant is a total of 100 g of monomers It can be used in an amount of 0.01 mmol to 10 mmol based on.
- the modifier may be used in a molar ratio of 1:0.1 to 10, 1: 0.1 to 5, or 1:0.1 to 1:3, based on 1 mole of the polymerization initiator in step (S1).
- step (S3) is a step for preparing a modified conjugated diene-based polymer by reacting a macromonomer including an active first chain and a repeating unit derived from the compound represented by Chemical Formula 1.
- the macromonomer may further include a unit derived from a conjugated diene-based monomer.
- condensation reaction in which the active polymer is modified with a modifier and a compound capable of condensation with the Si-O bond of the modifier has been applied as a way to additionally introduce a functional group into the polymer.
- the condensation reaction is used in this way, the bond between the substance having an additional functional group and the modified active polymer is formed into -Si-O-Si-, and hydrolysis may occur during the subsequent steam stripping step, washing step, or storage. Is present, and thus there is a problem in that the bond is separated at the condensation bonding site, resulting in a problem in which a functional group is lost.
- the present invention provides a rubber composition comprising the modified conjugated diene-based polymer.
- the Mooney viscosity (MV, (ML1+4, @100°C) MU) was measured using a Rotor Speed 2 ⁇ 0.02 rpm, Large Rotor at 100°C using MV-2000 (ALPHA Technologies). Samples were left at room temperature (23 ⁇ 3°C) for at least 30 minutes, and then 27 ⁇ 3 g was collected, filled in the die cavity, and platen was operated to measure for 4 minutes.
- TMQ(RD) (2,2,4-trimethyl-1,2-dihydroquinoline polymer)
- anti-aging agent (6PPD ((dimethylbutyl)-N-phenyl-phenylenediamine)
- wax Merocrystaline Wax
- Examples 1 to 4 exhibited remarkably improved tensile properties and processability properties while exhibiting viscoelastic properties equal to or higher than Comparative Example 3, and in this case, Comparative Example 3 used the macromonomer in Example 1 as a denaturation initiator, and modified reaction It is a modified styrene-butadiene copolymer prepared in the same manner as in Example 1, except that the step of reacting with the macromonomer was not performed thereafter.
- the present invention-modified conjugated diene-based polymer through the difference in the manufacturing method of Example 1 and Comparative Example 3 and the remarkable difference in effect between Example 1 and Comparative Example 3 despite the fact that the Si atom and N atom in the polymer are contained at the same level.
- a copolymer having a structure different from that of Comparative Example 3 for example, a second chain containing a repeating unit derived from a compound represented by Formula 1 derived from a macromonomer is coupled to the first chain of a modified polymer by a unit derived from a denaturant.
- n-hexane 3 kg of n-hexane, 215 g of styrene, 745 g of 1,3-butadiene, and 1.29 g of 2,2-bis(2-oxoranyl)propane as a polar additive were added, and then n-butyl Lithium 3.2 g (10wt% in n-hexane) was added, and the internal temperature of the reactor was adjusted to 60°C, and an adiabatic heating reaction was performed.
- Example 5 a solution containing the macromonomer prepared in Preparation Example 3 instead of n-butyllithium was added in an amount such that n-butyllithium of Example 5 and the macromonomer became equimolar to proceed with an adiabatic heating reaction. Then, a modified styrene-butadiene copolymer was prepared in the same manner as in Example 5, except that the step of adding and reacting a denaturant and a macromonomer was not performed, and the reaction was stopped after capping butadiene.
- the styrene unit content, vinyl content, and weight average molecular weight (Mw, X10 3 g/mol), number average molecular weight (Mn, X10 3 g) in the polymer, respectively. /mol), molecular weight distribution (PDI, MWD), Mooney viscosity (MV), Si atom and N atom content were measured in the same manner as in Experiment #1, respectively. The results are shown in Table 4 below.
- the modified conjugated diene-based polymer of the present invention is a copolymer having a structure different from that of Comparative Examples 7 and 8, for example, a polymer in which a second chain including a repeating unit derived from a compound represented by Formula 1 derived from a macromonomer is modified.
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Abstract
Description
Claims (13)
- 공액디엔계 단량체 유래 반복단위를 포함하는 제1사슬; 하기 화학식 1로 표시되는 화합물 유래 반복단위를 포함하는 제2사슬; 및 알콕시실란계 변성제 유래 단위를 포함하고, A first chain comprising a repeating unit derived from a conjugated diene-based monomer; A second chain comprising a repeating unit derived from a compound represented by the following formula (1); And a unit derived from an alkoxysilane modifier,상기 제1사슬과 제2사슬은 변성제 유래 단위에 의하여 커플링 결합되어 있는 것인 변성 공액디엔계 중합체:The modified conjugated diene-based polymer wherein the first chain and the second chain are coupled by a unit derived from a denaturant:[화학식 1][Formula 1]상기 화학식 1에서, In Formula 1,R1a 내지 R1c는 서로 독립적으로 수소 원자; 탄소수 1 내지 20의 알킬기; 탄소수 2 내지 20의 알케닐기; 탄소수 2 내지 20의 알카이닐기; 탄소수 1 내지 20의 헤테로알킬기, 탄소수 2 내지 20의 헤테로알케닐기; 탄소수 2 내지 20의 헤테로알카이닐기; 탄소수 5 내지 20의 시클로알킬기; 탄소수 6 내지 20의 아릴기; 또는 탄소수 3 내지 20의 헤테로고리기이며,R 1a to R 1c are each independently a hydrogen atom; An alkyl group having 1 to 20 carbon atoms; An alkenyl group having 2 to 20 carbon atoms; An alkynyl group having 2 to 20 carbon atoms; A C1-C20 heteroalkyl group, a C2-C20 heteroalkenyl group; A heteroalkynyl group having 2 to 20 carbon atoms; A cycloalkyl group having 5 to 20 carbon atoms; Aryl group having 6 to 20 carbon atoms; Or a heterocyclic group having 3 to 20 carbon atoms,R1d는 단일결합, 치환기로 치환되거나 비치환된 탄소수 1 내지 20의 알킬렌기; 치환기로 치환 또는 비치환된 탄소수 5 내지 20의 시클로알킬렌기; 또는 치환기로 치환 또는 비치환된 탄소수 6 내지 20의 아릴렌기이고, 여기에서 상기 치환기는 탄소수 1 내지 10의 알킬기, 탄소수 5 내지 10의 시클로알킬기, 또는 탄소수 6 내지 20의 아릴기이고, R 1d is a single bond, an alkylene group having 1 to 20 carbon atoms unsubstituted or substituted with a substituent; A cycloalkylene group having 5 to 20 carbon atoms substituted or unsubstituted with a substituent; Or an arylene group having 6 to 20 carbon atoms substituted or unsubstituted with a substituent, wherein the substituent is an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, or an aryl group having 6 to 20 carbon atoms,R1e는 탄소수 1 내지 20의 알킬기; 탄소수 2 내지 20의 알케닐기; 탄소수 2 내지 20의 알카이닐기; 탄소수 1 내지 20의 헤테로알킬기; 탄소수 2 내지 20의 헤테로알케닐기; 탄소수 2 내지 20의 헤테로알카이닐기; 탄소수 5 내지 20의 시클로알킬기; 탄소수 6 내지 20의 아릴기; 탄소수 3 내지 20의 헤테로고리기; 또는 하기 화학식 1a로 표시되는 치환기이며, R 1e is an alkyl group having 1 to 20 carbon atoms; An alkenyl group having 2 to 20 carbon atoms; An alkynyl group having 2 to 20 carbon atoms; A heteroalkyl group having 1 to 20 carbon atoms; A heteroalkenyl group having 2 to 20 carbon atoms; A heteroalkynyl group having 2 to 20 carbon atoms; A cycloalkyl group having 5 to 20 carbon atoms; Aryl group having 6 to 20 carbon atoms; A heterocyclic group having 3 to 20 carbon atoms; Or a substituent represented by the following formula 1a,[화학식 1a][Formula 1a]상기 화학식 1a에서, In Formula 1a,R1f는 단일결합, 치환기로 치환 또는 비치환된 탄소수 1 내지 20의 알킬렌기; 치환기로 치환 또는 비치환된 탄소수 5 내지 20의 시클로알킬렌기; 또는 치환기로 치환 또는 비치환된 탄소수 6 내지 20의 아릴렌기이고, 여기에서 상기 치환기는 탄소수 1 내지 10의 알킬기, 탄소수 5 내지 10의 시클로알킬기, 또는 탄소수 6 내지 20의 아릴기이고, R 1f is a single bond, an alkylene group having 1 to 20 carbon atoms unsubstituted or substituted with a substituent; A cycloalkylene group having 5 to 20 carbon atoms substituted or unsubstituted with a substituent; Or an arylene group having 6 to 20 carbon atoms substituted or unsubstituted with a substituent, wherein the substituent is an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, or an aryl group having 6 to 20 carbon atoms,R1g 및 R1h는 서로 독립적으로 탄소수 1 내지 20의 알킬기; 탄소수 2 내지 20의 알케닐기; 탄소수 2 내지 20의 알카이닐기; 탄소수 1 내지 20의 헤테로알킬기; 탄소수 2 내지 20의 헤테로알케닐기; 탄소수 2 내지 20의 헤테로알카이닐기; 탄소수 5 내지 20의 시클로알킬기; 탄소수 6 내지 20의 아릴기; 또는 탄소수 3 내지 20의 헤테로고리기이거나, 또는 R1g 및 R1h는 서로 연결되어 N과 함께 탄소수 2 내지 10의 헤테로고리기를 형성하는 것이다.R 1g and R 1h are each independently an alkyl group having 1 to 20 carbon atoms; An alkenyl group having 2 to 20 carbon atoms; An alkynyl group having 2 to 20 carbon atoms; A heteroalkyl group having 1 to 20 carbon atoms; A heteroalkenyl group having 2 to 20 carbon atoms; A heteroalkynyl group having 2 to 20 carbon atoms; A cycloalkyl group having 5 to 20 carbon atoms; Aryl group having 6 to 20 carbon atoms; Or a heterocyclic group having 3 to 20 carbon atoms, or R 1g and R 1h are connected to each other to form a heterocyclic group having 2 to 10 carbon atoms together with N.
- 청구항 1에 있어서, The method according to claim 1,상기 화학식 1에서, In Formula 1,R1a 내지 R1c는 서로 독립적으로 수소 원자; 탄소수 1 내지 10의 알킬기; 탄소수 2 내지 10의 알케닐기; 탄소수 2 내지 10의 알카이닐기; 탄소수 1 내지 10의 헤테로알킬기, 탄소수 2 내지 10의 헤테로알케닐기; 탄소수 2 내지 10의 헤테로알카이닐기; 탄소수 5 내지 10의 시클로알킬기; 탄소수 6 내지 10의 아릴기; 또는 탄소수 3 내지 10의 헤테로고리기이며,R 1a to R 1c are each independently a hydrogen atom; An alkyl group having 1 to 10 carbon atoms; An alkenyl group having 2 to 10 carbon atoms; An alkynyl group having 2 to 10 carbon atoms; A C1-C10 heteroalkyl group, a C2-C10 heteroalkenyl group; A heteroalkynyl group having 2 to 10 carbon atoms; A cycloalkyl group having 5 to 10 carbon atoms; Aryl group having 6 to 10 carbon atoms; Or a heterocyclic group having 3 to 10 carbon atoms,R1d는 단일결합 또는 비치환된 탄소수 1 내지 10의 알킬렌기이고, R 1d is a single bond or an unsubstituted C 1 to C 10 alkylene group,R1e는 탄소수 1 내지 10의 알킬기; 탄소수 2 내지 10의 알케닐기; 탄소수 2 내지 10의 알카이닐기; 탄소수 1 내지 10의 헤테로알킬기; 탄소수 2 내지 10의 헤테로알케닐기; 탄소수 2 내지 10의 헤테로알카이닐기; 탄소수 5 내지 10의 시클로알킬기; 탄소수 6 내지 10의 아릴기; 탄소수 3 내지 10의 헤테로고리기; 또는 화학식 1a로 표시되는 치환기이며, R 1e is an alkyl group having 1 to 10 carbon atoms; An alkenyl group having 2 to 10 carbon atoms; An alkynyl group having 2 to 10 carbon atoms; A heteroalkyl group having 1 to 10 carbon atoms; A heteroalkenyl group having 2 to 10 carbon atoms; A heteroalkynyl group having 2 to 10 carbon atoms; A cycloalkyl group having 5 to 10 carbon atoms; Aryl group having 6 to 10 carbon atoms; A heterocyclic group having 3 to 10 carbon atoms; Or a substituent represented by Formula 1a,상기 화학식 1a에서, In Formula 1a,R1f는 단일결합 또는 비치환된 탄소수 1 내지 10의 알킬렌기이고. R 1f is a single bond or an unsubstituted C 1 to C 10 alkylene group.R1g 및 R1h는 서로 독립적으로 탄소수 1 내지 10의 알킬기; 탄소수 2 내지 10의 알케닐기; 탄소수 2 내지 10의 알카이닐기; 탄소수 1 내지 10의 헤테로알킬기; 탄소수 2 내지 10의 헤테로알케닐기; 탄소수 2 내지 10의 헤테로알카이닐기; 탄소수 5 내지 10의 시클로알킬기; 탄소수 6 내지 10의 아릴기; 또는 탄소수 3 내지 10의 헤테로고리기이거나, 또는 R1g 및 R1h는 서로 연결되어 N과 함께 탄소수 2 내지 10의 헤테로고리기를 형성하는 것인 변성 공액디엔계 중합체.R 1g and R 1h are each independently an alkyl group having 1 to 10 carbon atoms; An alkenyl group having 2 to 10 carbon atoms; An alkynyl group having 2 to 10 carbon atoms; A heteroalkyl group having 1 to 10 carbon atoms; A heteroalkenyl group having 2 to 10 carbon atoms; A heteroalkynyl group having 2 to 10 carbon atoms; A cycloalkyl group having 5 to 10 carbon atoms; Aryl group having 6 to 10 carbon atoms; Or a C3-C10 heterocyclic group, or R 1g and R 1h are connected to each other to form a C2-C10 heterocyclic group with N to form a modified conjugated diene-based polymer.
- 제1항에 있어서,The method of claim 1,상기 화학식 1에서, In Formula 1,R1a 내지 R1c는 서로 독립적으로 수소 원자; 또는 탄소수 1 내지 6의 알킬기이고, R 1a to R 1c are each independently a hydrogen atom; Or an alkyl group having 1 to 6 carbon atoms,R1d는 단일결합 또는 비치환된 탄소수 1 내지 6의 알킬렌기이고, R 1d is a single bond or an unsubstituted C 1 to C 6 alkylene group,R1e는 탄소수 1 내지 10의 알킬기 또는 화학식 1a로 표시되는 치환기이며, R 1e is an alkyl group having 1 to 10 carbon atoms or a substituent represented by Formula 1a,상기 화학식 1a에서, In Formula 1a,R1f는 단일결합 또는 비치환된 탄소수 1 내지 6의 알킬렌기이고. R 1f is a single bond or an unsubstituted C 1 to C 6 alkylene group.R1g 및 R1h는 서로 독립적으로 탄소수 1 내지 10의 알킬기 이거나; 또는 R1g 및 R1h는 서로 연결되어 N과 함께 탄소수 2 내지 6의 헤테로고리기를 형성하는 것인 변성 공액디엔계 중합체.R 1g and R 1h are each independently an alkyl group having 1 to 10 carbon atoms; Or R 1g and R 1h are connected to each other to form a C2-C6 heterocyclic group with N.
- 제1항에 있어서, The method of claim 1,상기 제1사슬은 방향족 비닐계 단량체 유래 반복단위를 더 포함하는 것인 변성 공액디엔계 중합체.The first chain is a modified conjugated diene-based polymer further comprising a repeating unit derived from an aromatic vinyl-based monomer.
- 제1항에 있어서, The method of claim 1,상기 제2사슬은 공액디엔계 단량체 유래 단위를 더 포함하는 것인 변성 공액디엔계 중합체.The second chain is a modified conjugated diene-based polymer further comprising a unit derived from a conjugated diene-based monomer.
- 제1항에 있어서, The method of claim 1,상기 변성 공액디엔계 중합체는 수평균 분자량(Mn)이 1,000 g/mol 내지 2,000,000 g/mol이고, 중량평균 분자량(Mw)이 1,000 g/mol 내지 3,000,000 g/mol이고, 피크평균 분자량(Mp)이 1,000 g/mol 내지 3,000,000 g/mol인 변성 공액디엔계 중합체.The modified conjugated diene-based polymer has a number average molecular weight (Mn) of 1,000 g/mol to 2,000,000 g/mol, a weight average molecular weight (Mw) of 1,000 g/mol to 3,000,000 g/mol, and a peak average molecular weight (Mp) A modified conjugated diene-based polymer of 1,000 g/mol to 3,000,000 g/mol.
- 탄소 용매 중에서, 중합 개시제 존재 하에 공액디엔계 단량체 또는 공액디엔계 단량체와 방향족 비닐계 단량체를 중합하여 활성 제1사슬을 제조하는 단계(S1); Preparing an active first chain by polymerizing a conjugated diene-based monomer or a conjugated diene-based monomer and an aromatic vinyl-based monomer in a carbon solvent in the presence of a polymerization initiator (S1);상기 활성 제1사슬과 알콕시실란계 변성제를 반응시켜 변성된 활성 제1사슬을 제조하는 단계(S2); 및Preparing a modified active first chain by reacting the active first chain with an alkoxysilane-based modifier (S2); And상기 변성된 활성 제1사슬과 하기 화학식 1로 표시되는 화합물 유래 반복단위를 포함하는 마크로모노머를 반응시키는 단계(S3)를 포함하는 제1항의 변성 공액디엔계 중합체의 제조방법:A method for preparing a modified conjugated diene-based polymer of claim 1, comprising reacting (S3) a macromonomer including a repeating unit derived from a compound represented by the following formula (1) with the modified active first chain:[화학식 1][Formula 1]상기 화학식 1에서, In Formula 1,R1a 내지 R1c는 서로 독립적으로 수소 원자; 탄소수 1 내지 20의 알킬기; 탄소수 2 내지 20의 알케닐기; 탄소수 2 내지 20의 알카이닐기; 탄소수 1 내지 20의 헤테로알킬기, 탄소수 2 내지 20의 헤테로알케닐기; 탄소수 2 내지 20의 헤테로알카이닐기; 탄소수 5 내지 20의 시클로알킬기; 탄소수 6 내지 20의 아릴기; 또는 탄소수 3 내지 20의 헤테로고리기이며,R 1a to R 1c are each independently a hydrogen atom; An alkyl group having 1 to 20 carbon atoms; An alkenyl group having 2 to 20 carbon atoms; An alkynyl group having 2 to 20 carbon atoms; A C1-C20 heteroalkyl group, a C2-C20 heteroalkenyl group; A heteroalkynyl group having 2 to 20 carbon atoms; A cycloalkyl group having 5 to 20 carbon atoms; Aryl group having 6 to 20 carbon atoms; Or a heterocyclic group having 3 to 20 carbon atoms,R1d는 단일결합, 치환기로 치환되거나 비치환된 탄소수 1 내지 20의 알킬렌기; 치환기로 치환 또는 비치환된 탄소수 5 내지 20의 시클로알킬렌기; 또는 치환기로 치환 또는 비치환된 탄소수 6 내지 20의 아릴렌기이고, 여기에서 상기 치환기는 탄소수 1 내지 10의 알킬기, 탄소수 5 내지 10의 시클로알킬기, 또는 탄소수 6 내지 20의 아릴기이고, R 1d is a single bond, an alkylene group having 1 to 20 carbon atoms unsubstituted or substituted with a substituent; A cycloalkylene group having 5 to 20 carbon atoms substituted or unsubstituted with a substituent; Or an arylene group having 6 to 20 carbon atoms substituted or unsubstituted with a substituent, wherein the substituent is an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, or an aryl group having 6 to 20 carbon atoms,R1e는 탄소수 1 내지 20의 알킬기; 탄소수 2 내지 20의 알케닐기; 탄소수 2 내지 20의 알카이닐기; 탄소수 1 내지 20의 헤테로알킬기; 탄소수 2 내지 20의 헤테로알케닐기; 탄소수 2 내지 20의 헤테로알카이닐기; 탄소수 5 내지 20의 시클로알킬기; 탄소수 6 내지 20의 아릴기; 탄소수 3 내지 20의 헤테로고리기; 또는 하기 화학식 1a로 표시되는 치환기이며, R 1e is an alkyl group having 1 to 20 carbon atoms; An alkenyl group having 2 to 20 carbon atoms; An alkynyl group having 2 to 20 carbon atoms; A heteroalkyl group having 1 to 20 carbon atoms; A heteroalkenyl group having 2 to 20 carbon atoms; A heteroalkynyl group having 2 to 20 carbon atoms; A cycloalkyl group having 5 to 20 carbon atoms; Aryl group having 6 to 20 carbon atoms; A heterocyclic group having 3 to 20 carbon atoms; Or a substituent represented by the following formula 1a,[화학식 1a][Formula 1a]상기 화학식 1a에서, In Formula 1a,R1f는 단일결합, 치환기로 치환 또는 비치환된 탄소수 1 내지 20의 알킬렌기; 치환기로 치환 또는 비치환된 탄소수 5 내지 20의 시클로알킬렌기; 또는 치환기로 치환 또는 비치환된 탄소수 6 내지 20의 아릴렌기이고, 여기에서 상기 치환기는 탄소수 1 내지 10의 알킬기, 탄소수 5 내지 10의 시클로알킬기, 또는 탄소수 6 내지 20의 아릴기이고, R 1f is a single bond, an alkylene group having 1 to 20 carbon atoms unsubstituted or substituted with a substituent; A cycloalkylene group having 5 to 20 carbon atoms substituted or unsubstituted with a substituent; Or an arylene group having 6 to 20 carbon atoms substituted or unsubstituted with a substituent, wherein the substituent is an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, or an aryl group having 6 to 20 carbon atoms,R1g 및 R1h는 서로 독립적으로 탄소수 1 내지 20의 알킬기; 탄소수 2 내지 20의 알케닐기; 탄소수 2 내지 20의 알카이닐기; 탄소수 1 내지 20의 헤테로알킬기; 탄소수 2 내지 20의 헤테로알케닐기; 탄소수 2 내지 20의 헤테로알카이닐기; 탄소수 5 내지 20의 시클로알킬기; 탄소수 6 내지 20의 아릴기; 또는 탄소수 3 내지 20의 헤테로고리기이거나, 또는 R1g 및 R1h는 서로 연결되어 N과 함께 탄소수 2 내지 10의 헤테로고리기를 형성하는 것이다.R 1g and R 1h are each independently an alkyl group having 1 to 20 carbon atoms; An alkenyl group having 2 to 20 carbon atoms; An alkynyl group having 2 to 20 carbon atoms; A heteroalkyl group having 1 to 20 carbon atoms; A heteroalkenyl group having 2 to 20 carbon atoms; A heteroalkynyl group having 2 to 20 carbon atoms; A cycloalkyl group having 5 to 20 carbon atoms; Aryl group having 6 to 20 carbon atoms; Or a heterocyclic group having 3 to 20 carbon atoms, or R 1g and R 1h are connected to each other to form a heterocyclic group having 2 to 10 carbon atoms together with N.
- 제7항에 있어서, The method of claim 7,상기 마크로모노머는 공액디엔계 단량체 유래 단위를 더 포함하는 것인 변성 공액디엔계 중합체의 제조방법,The method for producing a modified conjugated diene-based polymer wherein the macromonomer further comprises a unit derived from a conjugated diene-based monomer,
- 제7항에 있어서, The method of claim 7,상기 마크로모노머는 탄화수소 용매 중에서 유기리튬 화합물 존재 하에 화학식 1로 표시되는 화합물 또는 화학식 1로 표시되는 화합물과 공액디엔계 단량체를 저중합 반응시켜 제조하는 것인 변성 공액디엔계 중합체의 제조방법. The macromonomer is a method for producing a modified conjugated diene-based polymer to be prepared by a low polymerization reaction of a compound represented by Formula 1 or a compound represented by Formula 1 and a conjugated diene-based monomer in the presence of an organolithium compound in a hydrocarbon solvent.
- 제7항에 있어서, The method of claim 7,상기 변성제는 중합 개시제 1몰 대비 0.1몰 내지 10몰로 사용하는 것인 변성 공액디엔계 중합체의 제조방법.The method for producing a modified conjugated diene-based polymer to be used in an amount of 0.1 to 10 mol relative to 1 mol of the polymerization initiator.
- 제7항에 있어서, The method of claim 7,상기 마크로모노머는 중합 개시제 1몰 대비 0.1 내지 2.0 몰로 사용하는 것인 변성 공액디엔계 중합체의 제조방법. The method for producing a modified conjugated diene-based polymer, wherein the macromonomer is used in an amount of 0.1 to 2.0 moles relative to 1 mole of the polymerization initiator.
- 제1항의 변성 공액디엔계 중합체 및 충전제를 포함하는 고무 조성물.A rubber composition comprising the modified conjugated diene-based polymer of claim 1 and a filler.
- 제12항에 있어서, The method of claim 12,변성 공액디엔계 중합체 100 중량부를 기준으로 0.1 중량부 내지 200 중량부의 충전제를 포함하는 것인 고무 조성물.A rubber composition comprising 0.1 parts by weight to 200 parts by weight of a filler based on 100 parts by weight of the modified conjugated diene-based polymer.
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