JP6498790B2 - アニオン重合開始剤の製造方法、製造装置およびこれから製造されるアニオン重合開始剤 - Google Patents
アニオン重合開始剤の製造方法、製造装置およびこれから製造されるアニオン重合開始剤 Download PDFInfo
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- JP6498790B2 JP6498790B2 JP2017560290A JP2017560290A JP6498790B2 JP 6498790 B2 JP6498790 B2 JP 6498790B2 JP 2017560290 A JP2017560290 A JP 2017560290A JP 2017560290 A JP2017560290 A JP 2017560290A JP 6498790 B2 JP6498790 B2 JP 6498790B2
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- polymerization initiator
- anionic polymerization
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- carbon atoms
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- 239000003505 polymerization initiator Substances 0.000 title claims description 71
- 238000010539 anionic addition polymerization reaction Methods 0.000 title claims description 69
- 238000004519 manufacturing process Methods 0.000 title claims description 42
- -1 amine compounds Chemical class 0.000 claims description 77
- 125000004432 carbon atom Chemical group C* 0.000 claims description 59
- 238000006243 chemical reaction Methods 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 41
- 239000000126 substance Substances 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 230000003068 static effect Effects 0.000 claims description 29
- 150000002902 organometallic compounds Chemical class 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 230000035484 reaction time Effects 0.000 claims description 14
- 229910052744 lithium Inorganic materials 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 150000002736 metal compounds Chemical class 0.000 claims 2
- 239000000243 solution Substances 0.000 description 52
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 38
- 239000003999 initiator Substances 0.000 description 24
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 14
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 13
- CGQMSVZSAGRUJH-UHFFFAOYSA-N 1-(3-ethenylphenyl)-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC(C=C)=C1 CGQMSVZSAGRUJH-UHFFFAOYSA-N 0.000 description 11
- 239000012530 fluid Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 238000003860 storage Methods 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000010586 diagram Methods 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229910052749 magnesium Inorganic materials 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
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- 239000000047 product Substances 0.000 description 6
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- 239000000376 reactant Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
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- 238000010517 secondary reaction Methods 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229920003048 styrene butadiene rubber Polymers 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 150000001993 dienes Chemical class 0.000 description 4
- 229910001623 magnesium bromide Inorganic materials 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- YVLKCQAGVDGTRH-UHFFFAOYSA-N 1-(2-ethenylphenyl)-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC=C1C=C YVLKCQAGVDGTRH-UHFFFAOYSA-N 0.000 description 3
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 238000010923 batch production Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 description 2
- XQBHAZDVLGNSOJ-UHFFFAOYSA-N 1-(4-ethenylphenyl)-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=C(C=C)C=C1 XQBHAZDVLGNSOJ-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
- FZLHAQMQWDDWFI-UHFFFAOYSA-N 2-[2-(oxolan-2-yl)propan-2-yl]oxolane Chemical compound C1CCOC1C(C)(C)C1CCCO1 FZLHAQMQWDDWFI-UHFFFAOYSA-N 0.000 description 2
- CSBDTEMAXHVRBB-UHFFFAOYSA-N 2-ethoxy-n,n-dimethylethanamine Chemical compound CCOCCN(C)C CSBDTEMAXHVRBB-UHFFFAOYSA-N 0.000 description 2
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001339 alkali metal compounds Chemical class 0.000 description 2
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical class NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 238000004891 communication Methods 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 230000002779 inactivation Effects 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 238000005304 joining Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 2
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000003512 tertiary amines Chemical group 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 2
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- GNLJBJNONOOOQC-UHFFFAOYSA-N $l^{3}-carbane;magnesium Chemical compound [Mg]C GNLJBJNONOOOQC-UHFFFAOYSA-N 0.000 description 1
- BOGRNZQRTNVZCZ-AATRIKPKSA-N (3e)-3-methylpenta-1,3-diene Chemical compound C\C=C(/C)C=C BOGRNZQRTNVZCZ-AATRIKPKSA-N 0.000 description 1
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- BOGRNZQRTNVZCZ-UHFFFAOYSA-N 1,2-dimethyl-butadiene Natural products CC=C(C)C=C BOGRNZQRTNVZCZ-UHFFFAOYSA-N 0.000 description 1
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
- ZWPUOFSQNASCII-UHFFFAOYSA-N 1-(2-ethoxyethoxy)butane Chemical group CCCCOCCOCC ZWPUOFSQNASCII-UHFFFAOYSA-N 0.000 description 1
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229940043430 calcium compound Drugs 0.000 description 1
- 150000001674 calcium compounds Chemical class 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
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- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 239000000446 fuel Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 150000002681 magnesium compounds Chemical class 0.000 description 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- HQHSMYARHRXIDS-UHFFFAOYSA-N n,n-dimethyl-1-phenylprop-2-en-1-amine Chemical class CN(C)C(C=C)C1=CC=CC=C1 HQHSMYARHRXIDS-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 150000003438 strontium compounds Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Description
下記化学式1および2の化合物の中から選ばれる1種以上のアミン化合物および有機金属化合物を連続式反応器に投入し、反応させる段階を含むアニオン重合開始剤の製造方法を提供する:
R1、R2、R3、R5、R6、R7、R8およびR9は、独立して、水素または炭素数1〜6のアルキル基を示し、
RaおよびRbは、独立して、水素または炭素数1〜5のアルキル基を示し、
nおよびmは、0〜20の整数であり、
R11、R12、R13およびR14は、独立して、水素、炭素数1〜6のアルキル基、炭素数1〜6のアルケニル基または炭素数1〜6のアルキニル基を示し、
X1、X2、X3、X4およびX5は、独立して、窒素または炭素を示し、且つ、少なくとも一つは窒素であり、
aは、0〜20の整数である。
混合器と、
前記混合器に連結される第1流入ラインおよび第2流入ラインと、を含み、
第1流入ラインは、請求項1に記載の化学式1および2の化合物の中から選ばれる1種以上のアミン化合物を供給し、第2流入ラインは、有機金属化合物を供給することを特徴とするアニオン重合開始剤の製造装置を提供する。
下記化学式9および10の化合物の中から選ばれるアニオン重合開始剤を提供する:
R4は、炭素数1〜20のアルキルリチウム、炭素数1〜20のアルキルソジウム、炭素数1〜20のアルキルカリウム、炭素数1〜6のアルキルマグネシウムブロミドまたは炭素数1〜6のアルキルマグネシウムクロリドを示し、
R5、R6、R7、R8およびR9は、水素または炭素数1〜6のアルキル基を示し、
RaおよびRbは、独立して、水素または炭素数1〜5のアルキル基を示し、
mおよびnは、0〜20の整数であり、
R14は、水素または炭素数1〜6のアルキル基を示し、
R15は、炭素数1〜20のアルキルリチウム、炭素数1〜20のアルキルソジウム、炭素数1〜20のアルキルカリウム、炭素数1〜6のアルキルマグネシウムブロミドまたは炭素数1〜6のアルキルマグネシウムクロリドを示し、
X1、X2、X3、X4およびX5は、独立して、窒素または炭素を示し、且つ、少なくとも一つは、窒素であり、
aは、0〜20の整数である。
下記化学式1および2の化合物の中から選ばれる1種以上のアミン化合物および有機金属化合物を連続式反応器に投入して反応させる段階を含むアニオン重合開始剤の製造方法を提供する:
R1、R2、R3、R5、R6、R7、R8およびR9は、独立して、水素または炭素数1〜6のアルキル基を示し、
RaおよびRbは、独立して、水素または炭素数1〜5のアルキル基を示し、
nおよびmは、0〜20の整数であり、
R11、R12、R13およびR14は、独立して、水素、炭素数1〜6のアルキル基、炭素数1〜6のアルケニル基または炭素数1〜6のアルキニル基を示し、
X1、X2、X3、X4およびX5は、独立して、窒素または炭素を示し、且つ、少なくとも一つは、窒素であり、
aは、0〜20の整数である。
RaおよびRbは、独立して、水素または炭素数1〜5のアルキル基を示し、
mは、0〜20の整数である。
R11、R12、R13およびR14は、水素、炭素数1〜6のアルキル基、炭素数1〜6のアルケニル基または炭素数1〜6のアルキニル基を示し、
a1は、0〜10の整数である。
R11、R12、R13およびR14は、水素または炭素数1〜6のアルキル基、炭素数1〜6のアルケニル基または炭素数1〜6のアルキニル基を示す。
混合器と、
前記混合器に連結される第1流入ラインおよび第2流入ラインと、を含み、
第1流入ラインは、請求項1に記載の化学式1および2の化合物の中から選ばれる1種以上のアミン化合物を供給し、第2流入ラインは、有機金属化合物を供給することを特徴とするアニオン重合開始剤の製造装置を提供する。
第3流入ラインは、共役ジエン化合物を供給できる。
下記化学式9および化学式10の化合物の中から選ばれるアニオン重合開始剤を提供する:
R4は、炭素数1〜20のアルキルリチウム、炭素数1〜20のアルキルソジウム、炭素数1〜20のアルキルカリウム、炭素数1〜6のアルキルマグネシウムブロミドまたは炭素数1〜6のアルキルマグネシウムクロリドを示し、
R5、R6、R7、R8およびR9は、水素または炭素数1〜6のアルキル基を示し、
RaおよびRbは、独立して、水素または炭素数1〜5のアルキル基を示し、
nおよびmは、0〜20の整数であり、
R14は、水素または炭素数1〜6のアルキル基を示し、
R15は、炭素数1〜20のアルキルリチウム、炭素数1〜20のアルキルソジウム、炭素数1〜20のアルキルカリウム、炭素数1〜6のアルキルマグネシウムブロミドまたは炭素数1〜6のアルキルマグネシウムクロリドを示し、
X1、X2、X3、X4およびX5は、独立して、窒素または炭素を示し、且つ、少なくとも一つは窒素であり、
aは、0〜20の整数である。
R10は、炭素数1〜20のアルキルリチウムを示し、
RaおよびRbは、独立して、水素または炭素数1〜5のアルキル基を示し、
m1は、0〜10の整数である。
R14は、水素または炭素数1〜6のアルキル基を示し、
R16は、炭素数1〜20のアルキルリチウムを示し、
a1は、0〜10の整数である。
真空乾燥させた3つのステンレススチール圧力容器を準備した。第1の圧力容器にヘキサン47g、3−ビニル−N、N−ジメチルベンジルアミン100gおよびテトラメチルエチレンジアミン101gを入れ、3−ビニル−N、N−ジメチルベンジルアミン溶液を製造した。そして、他の圧力容器に2.5M液相n−ブチルリチウム171gおよびヘキサン77gを入れ、n−ブチルリチウム溶液を製造した。
3−ビニル−N、N−ジメチルベンジルアミン溶液の他に、2−ビニル−N、N−ジメチルベンジルアミン、3−ビニル−N、N−ジメチルベンジルアミンおよび4−ビニル−N、N−ティメティルベンジラミンの異性体が混合された混合溶液を使用したことを除いて、実施例1と同一に製造した。
チューブ反応器でなく、スタティックミキサーを使用したことを除いて、実施例1と同一に製造した。
真空乾燥させた3つのステンレススチール圧力容器を準備した。 第1の圧力容器にヘキサン1000g、2−ビニルピリジン82gおよびテトラメチルエチレンジアミン911gを入れ、2−ビニルピリジン溶液を製造した。そして、他の圧力容器に2.0M液相n−ブチルリチウム484gおよびシクロヘシサン981gを入れ、n−ブチルリチウム溶液を製造した。
2−ビニルピリジンの代わりに、2−ビニルピリジンおよび4−ビニルピリジンを含む異性体混合溶液を使用したことを除いて、実施例4と同一に製造した。
チューブ反応器およびスタティックミキサーを混合して使用したことを除いて、実施例4と同一に製造した。
実施例1〜6のアミン化合物および共役ジエン化合物の転換率を気体クロマトグラフィー(GC)で分析し、次の数式1で計算した。
アミン化合物または共役ジエン化合物の転換率(%)=100×(初期アミン化合物または共役ジエン化合物の濃度−反応後のアミン化合物または共役ジエン化合物の濃度)/初期アミン化合物または共役ジエン化合物の濃度
Claims (12)
- 下記化学式2および3の化合物の中から選ばれる1種以上のアミン化合物および有機金属化合物を連続式反応器に投入し、反応させる段階;および
前記化学式2および3の化合物の中から選ばれる1種以上のアミン化合物および有機金属化合物を反応させる段階後に、共役ジエン化合物を連続式反応器に供給する段階
を含むアニオン重合開始剤の製造方法。
前記化学式2で、
R11、R12、R13およびR14は、独立して、水素、炭素数1〜6のアルキル基、炭素数1〜6のアルケニル基または炭素数1〜6のアルキニル基を示し、
X1、X2、X3、X4およびX5は、独立して、窒素または炭素を示し、且つ、少なくとも一つは、窒素であり、
aは、0〜20の整数である。
前記化学式3で、
R a およびR b は、独立して、水素または炭素数1〜5のアルキル基を示し、
mは、0〜20の整数である。 - 化学式2の化合物は、下記化学式4または5の化合物であることを特徴とする請求項1に記載のアニオン重合開始剤の製造方法。
前記化学式4および5で、
R11、R12、R13およびR14は、水素、炭素数1〜6のアルキル基、炭素数1〜6のアルケニル基または炭素数1〜6のアルキニル基を示し、
a1は、0〜10の整数である。 - 有機金属化合物は、有機アルカリ金属化合物および有機アルカリ土類金属化合物よりなる群から選ばれる1種以上を含むことを特徴とする請求項1または2に記載のアニオン重合開始剤の製造方法。
- 前記化学式3および2の化合物の中から選ばれる1種以上のアミン化合物と有機金属化合物のモル比は、5:1〜1:5であることを特徴とする請求項1〜3のいずれか一項に記載のアニオン重合開始剤の製造方法。
- 前記化学式3および2の化合物の中から選ばれる1種以上のアミン化合物と共役ジエン化合物のモル比は、1:1〜1:100であることを特徴とする請求項1〜4のいずれか一項に記載のアニオン重合開始剤の製造方法。
- 直列に連結される第1混合器および第2混合器と、
前記第1混合器に連結される第1流入ラインおよび第2流入ラインと、
前記第2混合器に連結される第3流入ラインとを含み、
前記第1流入ラインは、請求項1に記載の化学式2および3の化合物の中から選ばれる1種以上のアミン化合物を供給し、
前記第2流入ラインは、有機金属化合物を供給し、
前記第3流入ラインは、共役ジエン化合物を供給することを特徴とするアニオン重合開始剤の製造装置。 - 第1および第2混合器のいずれか一つ以上は、スタティックミキサーであることを特徴とする請求項6に記載のアニオン重合開始剤の製造装置。
- スタティックミキサーは、それぞれ独立して、プレートミキサー、ケニクス(Kenics)ミキサーおよびスルザー(Sulzer)ミキサーよりなる群から選ばれる1種以上であることを特徴とする請求項7に記載のアニオン重合開始剤の製造装置。
- 第1および第2混合器のいずれか一つ以上は、マイクロ反応器であり、
前記マイクロ反応器は、分岐および合流を繰り返す複数の微細チャネルを含むことを特徴とする請求項6に記載のアニオン重合開始剤の製造装置。 - 第1および第2混合器のいずれか一つ以上は、スタティックミキサーおよびマイクロ反応器が連結された構造であることを特徴とする請求項6に記載のアニオン重合開始剤の製造装置。
- 第1混合器の反応温度は、−80℃〜100℃であり、反応時間は、0.001〜90分であり、
第2混合器の反応温度は、10℃〜100℃であり、反応時間は、1〜60分であることを特徴とする請求項6〜10のいずれか一項に記載のアニオン重合開始剤の製造装置。 - 下記化学式11、14および15の化合物の中から選ばれるアニオン重合開始剤。
R 10 は、炭素数1〜20のアルキルリチウムを示し、
R a およびR b は、独立して、水素または炭素数1〜5のアルキル基を示し、
m 1 は、0〜10の整数である。
R 14 は、水素または炭素数1〜6のアルキル基を示し、
R 16 は、炭素数3〜20のアルキルリチウムを示し、
a 1 は、0〜10の整数である。
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