JP6896303B2 - エチレン/アルファ−オレフィン共重合体 - Google Patents
エチレン/アルファ−オレフィン共重合体 Download PDFInfo
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- JP6896303B2 JP6896303B2 JP2019507816A JP2019507816A JP6896303B2 JP 6896303 B2 JP6896303 B2 JP 6896303B2 JP 2019507816 A JP2019507816 A JP 2019507816A JP 2019507816 A JP2019507816 A JP 2019507816A JP 6896303 B2 JP6896303 B2 JP 6896303B2
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- Prior art keywords
- alpha
- ethylene
- group
- olefin copolymer
- olefin
- Prior art date
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- 239000004711 α-olefin Substances 0.000 title claims description 78
- 239000005977 Ethylene Substances 0.000 title claims description 77
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims description 76
- 229920000089 Cyclic olefin copolymer Polymers 0.000 title claims description 57
- 239000013078 crystal Substances 0.000 claims description 69
- 230000006353 environmental stress Effects 0.000 claims description 26
- 229920001577 copolymer Polymers 0.000 claims description 24
- 238000004458 analytical method Methods 0.000 claims description 21
- 238000000235 small-angle X-ray scattering Methods 0.000 claims description 20
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 14
- 238000004364 calculation method Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 description 59
- 150000001875 compounds Chemical class 0.000 description 57
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- -1 Polyethylene Polymers 0.000 description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 125000000217 alkyl group Chemical group 0.000 description 26
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 23
- 241000446313 Lamella Species 0.000 description 22
- 239000000243 solution Substances 0.000 description 18
- 125000003118 aryl group Chemical group 0.000 description 17
- 239000012968 metallocene catalyst Substances 0.000 description 17
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 238000006116 polymerization reaction Methods 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- 239000003426 co-catalyst Substances 0.000 description 11
- 239000000178 monomer Substances 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 10
- 238000009826 distribution Methods 0.000 description 10
- 229910052736 halogen Inorganic materials 0.000 description 10
- 150000002367 halogens Chemical class 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 230000000704 physical effect Effects 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical class C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 8
- 239000003446 ligand Substances 0.000 description 8
- 229920000098 polyolefin Polymers 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- RURFJXKOXIWFJX-UHFFFAOYSA-N (2,3,4,6-tetrafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C=C(F)C(F)=C1F RURFJXKOXIWFJX-UHFFFAOYSA-N 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 125000002877 alkyl aryl group Chemical group 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 229920001903 high density polyethylene Polymers 0.000 description 6
- 239000004700 high-density polyethylene Substances 0.000 description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 229910052723 transition metal Inorganic materials 0.000 description 6
- 150000003624 transition metals Chemical class 0.000 description 6
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 239000012018 catalyst precursor Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000005314 correlation function Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer 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
- 230000037048 polymerization activity Effects 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000004279 X-ray Guinier Methods 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000005234 alkyl aluminium group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 125000005353 silylalkyl group Chemical group 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- JNBVLGDICHLLTN-DZUOILHNSA-N (2s)-2-acetamido-n-[(2s,3s)-4-[[[(2s)-2-acetamido-3-methylbutanoyl]amino]-(cyclohexylmethyl)amino]-3-hydroxy-1-phenylbutan-2-yl]-3-methylbutanamide Chemical compound C([C@H](NC(=O)[C@@H](NC(C)=O)C(C)C)[C@@H](O)CN(CC1CCCCC1)NC(=O)[C@@H](NC(C)=O)C(C)C)C1=CC=CC=C1 JNBVLGDICHLLTN-DZUOILHNSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-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
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 229910007926 ZrCl Inorganic materials 0.000 description 2
- 125000005103 alkyl silyl group Chemical group 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 125000005131 dialkylammonium group Chemical class 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-O diethyl(phenyl)azanium Chemical compound CC[NH+](CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-O 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-O dimethyl(phenyl)azanium Chemical compound C[NH+](C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-O 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052735 hafnium Inorganic materials 0.000 description 2
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 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 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- RXXXUIOZOITBII-UHFFFAOYSA-N indeno[1,2-g]indole Chemical class C1=C2C=CC=CC2=C2C1=C1N=CC=C1C=C2 RXXXUIOZOITBII-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000006263 metalation reaction Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 229920006126 semicrystalline polymer Polymers 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- WCFQIFDACWBNJT-UHFFFAOYSA-N $l^{1}-alumanyloxy(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]O[Al] WCFQIFDACWBNJT-UHFFFAOYSA-N 0.000 description 1
- 125000006657 (C1-C10) hydrocarbyl group Chemical group 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- YEKDCFFOCHECCJ-UHFFFAOYSA-N 1-chloro-5,5-dimethylhexane Chemical compound CC(C)(C)CCCCCl YEKDCFFOCHECCJ-UHFFFAOYSA-N 0.000 description 1
- HOPKIAZSJPYWMF-UHFFFAOYSA-N 2-[4-[(2-methylpropan-2-yl)oxy]butyl]cyclopenta-1,3-diene Chemical compound C(C)(C)(C)OCCCCC1=CCC=C1 HOPKIAZSJPYWMF-UHFFFAOYSA-N 0.000 description 1
- YVSMQHYREUQGRX-UHFFFAOYSA-N 2-ethyloxaluminane Chemical compound CC[Al]1CCCCO1 YVSMQHYREUQGRX-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000002879 Lewis base Substances 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- MKJDNIZTFUOTNB-UHFFFAOYSA-N OB(O)O.C(CC1)CCC1NC1CCCCC1.C(CC1)CCC1NC1CCCCC1.C(CC1)CCC1NC1CCCCC1 Chemical class OB(O)O.C(CC1)CCC1NC1CCCCC1.C(CC1)CCC1NC1CCCCC1.C(CC1)CCC1NC1CCCCC1 MKJDNIZTFUOTNB-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000005370 alkoxysilyl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
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- 230000003467 diminishing effect Effects 0.000 description 1
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- SRLHDBRENZFCIN-UHFFFAOYSA-N n,n-di(butan-2-yl)butan-2-amine Chemical compound CCC(C)N(C(C)CC)C(C)CC SRLHDBRENZFCIN-UHFFFAOYSA-N 0.000 description 1
- VFLWKHBYVIUAMP-UHFFFAOYSA-N n-methyl-n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCCCC VFLWKHBYVIUAMP-UHFFFAOYSA-N 0.000 description 1
- KUFYUMSBZMUWAN-UHFFFAOYSA-N n-methyl-n-tetradecyltetradecan-1-amine Chemical compound CCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCC KUFYUMSBZMUWAN-UHFFFAOYSA-N 0.000 description 1
- HSUGDXPUFCVGES-UHFFFAOYSA-N n-tetradecyltetradecan-1-amine Chemical compound CCCCCCCCCCCCCCNCCCCCCCCCCCCCC HSUGDXPUFCVGES-UHFFFAOYSA-N 0.000 description 1
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- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- FGTJJHCZWOVVNH-UHFFFAOYSA-N tert-butyl-[tert-butyl(dimethyl)silyl]oxy-dimethylsilane Chemical group CC(C)(C)[Si](C)(C)O[Si](C)(C)C(C)(C)C FGTJJHCZWOVVNH-UHFFFAOYSA-N 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
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
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Description
本出願は、2016年11月8日付の韓国特許出願第10−2016−0148267号に基づく優先権の利益を主張し、当該韓国特許出願の文献に開示されたすべての内容は本明細書の一部として含まれる。
ラメラ(lamellar)結晶を含む結晶性部分と、前記ラメラ結晶間の結合を媒介する連結分子を含む無定形部分とを含む結晶構造を有し、
SAXS(Small Anlge X−ray Scattering)分析結果から算出された前記ラメラ結晶の厚さ(dc)は12.0〜16.0nmであり、前記無定形部分の厚さ(da)は4.0〜5.3nmであり、前記da/dcの式から算出される厚さ比は0.3〜0.4であるエチレン/アルファ−オレフィン共重合体を提供する。
ラメラ(lamellar)結晶を含む結晶性部分と、前記ラメラ結晶間の結合を媒介する連結分子を含む無定形部分とを含む結晶構造を有し、
SAXS(Small Anlge X−ray Scattering)分析結果から算出された前記ラメラ結晶の厚さ(dc)は12.0〜16.0nmであり、前記無定形部分の厚さ(da)は4.0〜5.3nmであり、前記da/dcの式から算出される厚さ比は0.3〜0.4であるエチレン/アルファ−オレフィン共重合体が提供される。
dcおよびdaは、前記ラメラ結晶の厚さ(dc)および前記無定形部分の厚さ(da)を示し、
<r>は、分子量(Mw)に応じたランダムコイルの両末端間の距離(end−to−end distance of a random coil)を示し、
b2は、3/(2<r>2)である。
dcおよびdaは、前記ラメラ結晶の厚さ(dc)および前記無定形部分の厚さ(da)を示し、
<r>は、分子量(Mw)に応じたランダムコイルの両末端間の距離(end−to−end distance of a random coil)を示し、
b2は、3/(2<r>2)である。
Mは、4族遷移金属であり;
B1は、炭素、ケイ素、またはゲルマニウムであり;
Q1およびQ2は、互いに同一または異なり、それぞれ独立に、水素、ハロゲン、C1〜C20のアルキル基、C2〜C20のアルケニル基、C6〜C20のアリール基、C7〜C20のアルキルアリール基、C7〜C20のアリールアルキル基、C1〜C20のアルコキシ基、C2〜C20のアルコキシアルキル基、C3〜C20のヘテロシクロアルキル基、またはC5〜C20のヘテロアリール基であり;
X1およびX2は、互いに同一または異なり、それぞれ独立に、ハロゲン、C1〜C20のアルキル基、C2〜C20のアルケニル基、C6〜C20のアリール基、ニトロ基、アミド基、C1〜C20のアルキルシリル基、C1〜C20のアルコキシ基、またはC1〜C20のスルホネート基であり;
C1およびC2は、互いに同一または異なり、それぞれ独立に、下記化学式2a、化学式2b、化学式2c、または化学式2dのうちの1つで表され、ただし、C1およびC2のうちの1つ以上は、化学式2aで表され;
R1〜R28は、互いに同一または異なり、それぞれ独立に、水素、ハロゲン、C1〜C20のアルキル基、C2〜C20のアルケニル基、C1〜C20のアルキルシリル基、C1〜C20のシリルアルキル基、C1〜C20のアルコキシシリル基、C1〜C20のエーテル基、C1〜C20のシリルエーテル基、C1〜C20のアルコキシ基、C6〜C20のアリール基、C7〜C20のアルキルアリール基、またはC7〜C20のアリールアルキル基であり、
R’1〜R’3は、互いに同一または異なり、それぞれ独立に、水素、ハロゲン、C1〜C20のアルキル基、C2〜C20のアルケニル基、C6〜C20のアリール基であり、
前記R1〜R28のうち互いに隣接する2つ以上が互いに連結されて置換もしくは非置換の脂肪族または芳香族環を形成してもよい。
R31〜R38のうちのいずれか1つ以上は、−(CH2)n−OR(この時、Rは、C1〜C6の直鎖もしくは分枝鎖アルキル基であり、nは、2〜4の整数である。)であり、
残りは、互いに同一または異なり、それぞれ独立に、水素、C1〜C20のアルキル基、C2〜C20のアルケニル基、C6〜C20のアリール基、C7〜C20のアルキルアリール基、およびC7〜C20のアリールアルキル基からなる群より選択された官能基であるか、または互いに隣接する2つ以上が互いに連結されてC1〜C10のヒドロカルビル基で置換もしくは非置換の脂肪族または芳香族環を形成してもよく、
Q3およびQ4は、互いに同一または異なり、それぞれ独立に、ハロゲン、または炭素数1〜20のアルキル基であり;
M’は、4族遷移金属であり、
X3およびX4は、互いに同一または異なり、それぞれ独立に、ハロゲン、またはC1〜C20のアルキル基であり、
mは、0または1の整数である。
R31〜R38のうちのいずれか1つ以上は、−(CH2)n−OR(この時、Rは、C1〜C6の直鎖もしくは分枝鎖アルキル基であり、nは、2〜4の整数である。)であり、残りは、互いに同一または異なり、それぞれ独立に、水素、C1〜C20のアルキル基、C2〜C20のアルケニル基、C6〜C20のアリール基、C7〜C20のアルキルアリール基、およびC7〜C20のアリールアルキル基からなる群より選択された官能基であるか、または互いに隣接する2つ以上が互いに連結されてC1〜C10のヒドロカルビル基で置換もしくは非置換の脂肪族または芳香族環を形成してもよく、
Q3およびQ4は、互いに同一または異なり、それぞれ独立に、ハロゲン、またはC1〜C20のアルキル基であり;
M’は、4族遷移金属であり、
X3およびX4は、互いに同一または異なり、それぞれ独立に、ハロゲン、または炭素数1〜20のアルキル基であり、
mは、0または1の整数である。
−[Al(R39)−O−]k−
T+[BG4]−
<メタロセン化合物および担持触媒の製造実施例>
合成例1:第1メタロセン化合物の合成
乾燥した250mLのシュレンクフラスコ(schlenk flask)に2.331g(10mmol)のIndenoindoleを入れて、アルゴン下で40mLのエーテルを注入した。エーテル溶液を0℃まで冷却した後、4.8mL(12mmol)の2.5M nBuLi ヘキサン溶液をゆっくり滴加した。反応混合物はゆっくり常温に上げてから翌日まで撹拌した。他の250mLのシュレンクフラスコにエーテル20mLを満たした後、3.6mL(30mmol)のdichloromethyl(tertbutoxyhexyl)silaneを注入した。このフラスコを−78℃まで冷却した後、これにIndenoindoleのlithiated solutionをcannulaを通して注入した。注入が終わった混合物は常温にゆっくり上げてから約5時間撹拌させた後、1日間撹拌後、フラスコ内に50mlの水を入れてクエンチングし、有機層を分離してMgSO4で乾燥した。減圧下で溶媒として使用されたエーテルを除去した。これをNMRで確認して、約95%以上の純度の10−((6−(tert−butoxy)hexyl)chloro(methyl)silyl)−5,8−dimethyl−5,10−dihydroindeno[1,2−b]indoleを得た。
オーブンに乾燥した250mLのシュレンクフラスコにリガンドを入れてエーテルに溶かした後、2.1当量のnBuLi 溶液を加えて翌日までlithiationをさせた。グローブボックス内で1当量のZrCl4(THF)2を取って250mlのシュレンクフラスコに入れて、エーテルまたはトルエンを入れたsuspensionを準備した。前記2つのフラスコとも−78℃まで冷却させた後、ligand anionをゆっくりZr suspensionに加えた。注入が終わった後、反応混合物はゆっくり常温まで上げた。この過程でメタレーションが成功的に進行している場合、触媒前駆体特有の色である赤紫色が現れることが確認された。これを1日間撹拌後、混合物内のトルエンまたはエーテルを約1/5volumeまで真空減圧により除去し、残っている溶媒の5倍程度のvolumeのヘキサンを加えた。この時、ヘキサンを加える理由は、合成された触媒前駆体がヘキサンに対する溶解度が低下するため、結晶化を促進させるためである。このヘキサンスラリーをアルゴン下でフィルタし、ろ過後、フィルタされた固体とろ過液をすべて真空減圧下で蒸発させた。前記で残ったfilter cakeをグローブボックス内で計量し、サンプリングして、合成の有無と収率、純度を確認した。メタレーションの溶媒としてはエーテルを使用し、6.4g(10mmol)のリガンドから6.08g(76.5%)の赤紫色固体が得られた。
乾燥した250mLのシュレンクフラスコに10.8g(100mmol)のchlorobutanolを入れた後、10gのmolecular sieveと100mLのMTBEを加えた後、20gの硫酸を30分かけてゆっくり加えた。反応混合物は時間とともにゆっくりピンク色に変わり、16時間後に氷で冷たく冷やした飽和sodium bicarbonate溶液に注いだ。この混合物にエーテル(100mL×4)を加えて数回抽出し、集められた有機層はMgSO4で乾燥し、ろ過を経た後、真空減圧下で溶媒を除去して、黄色の液体形態の1−(tert butoxy)−4−chlorobutane10g(60%収率)を得た。
乾燥した250mLのシュレンクフラスコに1−1で合成したリガンド化合物4.3g(23mmol)を入れて、60mLのTHFに溶かした。これに11mLのn−BuLi 2.0M ヘキサン溶液(28mmol)を加えて1日間撹拌させた後、この溶液を、ZrCl4(THF)2 3.83g(10.3mmol)を50mLのエーテルに分散させたフラスコに、−78℃でゆっくり加えた。
300mLのガラス反応器にトルエン溶液50mLを入れて乾燥したシリカ(Grace Davison社製造、SP2410)10gを投入した後、反応器の温度を40℃に上げながら撹拌した。10重量%メチルアルミノキサン(MAO)/トルエン溶液を60mL投入し、60℃に温度を上げた後、200rpmで12時間撹拌した。反応器の温度を40℃に下げてから撹拌を中止し、10分間settlingした後、反応溶液をデカンテーション(decantation)した。再びトルエン100mLを投入し、10分間撹拌してから撹拌を中止し、10分間settlingした後、トルエン溶液をデカンテーションした。
実施例1
前記製造例1で製造した担持触媒50mgをドライボックスで定量して50mLのガラス瓶にそれぞれ入れた後、ゴム隔膜で密封してドライボックスから取り出して、注入する触媒を準備した。重合は、機械式撹拌機付きの、温度調節が可能で高圧で用いられる2L金属合金反応器で行った。
1−ブテンの注入量を30mLに変更したことを除けば、前記実施例1と同様の方法でエチレン/アルファ−オレフィン共重合体を製造した。
1−ブテンの注入量を5mLに変更したことを除けば、前記実施例1と同様の方法でエチレン/アルファ−オレフィン共重合体を製造した。
気体エチレン単量体の圧力を8Kgf/cm2に変更したことを除けば、前記実施例1と同様の方法でエチレン/アルファ−オレフィン共重合体を製造した。
気体エチレン単量体の圧力を7Kgf/cm2に変更したことを除けば、前記実施例1と同様の方法でエチレン/アルファ−オレフィン共重合体を製造した。
SAXS分析は、浦項加速器(PAL)、4Cビームラインを用いた。このようなSAXS分析により、実施例1に対する図2AのSAXS分析結果を導出し、実施例2に対しても同様の分析結果を導出した。
前記(3)のdcおよびdaの測定値と、下記式1の計算結果から、実施例/比較例の共重合体に含まれる連結分子の含有量比率(Tie Molecule fraction)を算出した。参照として、この式1中、分母の数式は、全体高分子鎖(ランダムコイル)の両末端の距離の分布を意味し、これにより、式1は、全体高分子鎖(ランダムコイル)の両末端の距離の分布において、2つのラメラ結晶とその間の無定形部分との距離に高分子鎖の両末端がある確率(つまり、連結分子の含有量比率として称される存在確率)を意味する。
dcおよびdaは、前記ラメラ結晶の厚さ(dc)および前記無定形部分の厚さ(da)を示し、
<r>は、分子量(Mw)に応じたランダムコイルの両末端間の距離(end−to−end distance of a random coil)を示し、
b2は、3/(2<r>2)である。
前記実施例および比較例で製造されたエチレン/アルファ−オレフィン共重合体に対して、下記の方法で物性を測定した。
Claims (4)
- エチレン繰り返し単位およびアルファ−オレフィン繰り返し単位を含むエチレン/アルファ−オレフィン共重合体であって、
前記アルファ−オレフィンは、1−ブテンであり、
ラメラ(lamellar)結晶を含む結晶性部分と、前記ラメラ結晶間の結合を媒介する連結分子を含む無定形部分とを含む結晶構造を有し、
SAXS(Small Anlge X−ray Scattering)分析結果から算出された前記ラメラ結晶の厚さ(dc)は12.0〜16.0nmであり、前記無定形部分の厚さ(da)は4.0〜5.3nmであり、前記da/dcの式から算出される厚さ比は0.3〜0.4であり、
前記共重合体の密度が0.934g/cm 3 〜0.938g/cm 3 であるエチレン/アルファ−オレフィン共重合体。 - 重量平均分子量(Mw)が85000g/mol〜150000g/molである、請求項1に記載のエチレン/アルファ−オレフィン共重合体。
- ASTM D1693により測定された耐環境応力亀裂性(ESCR、environmental stress crack resistance)が100時間以上である、請求項1に記載のエチレン/アルファオレフィン共重合体。
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KR101747401B1 (ko) * | 2014-12-08 | 2017-06-14 | 주식회사 엘지화학 | 가공성이 우수한 에틸렌/알파-올레핀 공중합체 |
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KR20160121940A (ko) * | 2015-04-13 | 2016-10-21 | 주식회사 엘지화학 | 내환경 응력 균열성이 우수한 에틸렌/알파-올레핀 공중합체 |
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KR102048521B1 (ko) | 2016-10-20 | 2019-11-25 | 주식회사 엘지화학 | 내환경 응력 균열성이 우수한 에틸렌/알파-올레핀 공중합체 |
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- 2017-10-25 CN CN202210387777.2A patent/CN114752010A/zh active Pending
- 2017-10-25 CN CN201780054787.1A patent/CN109890854A/zh active Pending
- 2017-10-25 US US16/323,991 patent/US10858465B2/en active Active
- 2017-10-25 JP JP2019507816A patent/JP6896303B2/ja active Active
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US10858465B2 (en) | 2020-12-08 |
CN114752010A (zh) | 2022-07-15 |
CN109890854A (zh) | 2019-06-14 |
EP3480221A1 (en) | 2019-05-08 |
KR20180051223A (ko) | 2018-05-16 |
EP3480221A4 (en) | 2019-07-17 |
US20190211122A1 (en) | 2019-07-11 |
KR101958015B1 (ko) | 2019-07-04 |
JP2019524963A (ja) | 2019-09-05 |
EP3480221B1 (en) | 2023-03-22 |
WO2018088725A1 (ko) | 2018-05-17 |
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