JP2021515825A - エチレン/アルファ−オレフィン共重合体及びその製造方法 - Google Patents
エチレン/アルファ−オレフィン共重合体及びその製造方法 Download PDFInfo
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- JP2021515825A JP2021515825A JP2020545271A JP2020545271A JP2021515825A JP 2021515825 A JP2021515825 A JP 2021515825A JP 2020545271 A JP2020545271 A JP 2020545271A JP 2020545271 A JP2020545271 A JP 2020545271A JP 2021515825 A JP2021515825 A JP 2021515825A
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- Prior art keywords
- alpha
- ethylene
- carbon atoms
- olefin copolymer
- molecular weight
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Links
- 239000004711 α-olefin Substances 0.000 title claims abstract description 73
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims abstract description 72
- 239000005977 Ethylene Substances 0.000 title claims abstract description 72
- 229920000089 Cyclic olefin copolymer Polymers 0.000 title claims abstract description 62
- 238000004519 manufacturing process Methods 0.000 title abstract description 16
- 238000009826 distribution Methods 0.000 claims abstract description 35
- 125000000524 functional group Chemical group 0.000 claims abstract description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 99
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 25
- 229920001577 copolymer Polymers 0.000 claims description 24
- 238000005481 NMR spectroscopy Methods 0.000 claims description 16
- 238000002844 melting Methods 0.000 claims description 16
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 16
- 229920002554 vinyl polymer Polymers 0.000 claims description 16
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 14
- 230000008018 melting Effects 0.000 claims description 14
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 12
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 12
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 10
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims description 4
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 claims description 4
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 claims description 4
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 claims description 4
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 claims description 4
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 claims description 4
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 4
- 229940069096 dodecene Drugs 0.000 claims description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 229940095068 tetradecene Drugs 0.000 claims 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 description 44
- 239000001257 hydrogen Substances 0.000 description 40
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 38
- 239000003054 catalyst Substances 0.000 description 35
- 239000000203 mixture Substances 0.000 description 31
- -1 polyethylene Polymers 0.000 description 30
- 239000000126 substance Substances 0.000 description 26
- 150000003623 transition metal compounds Chemical group 0.000 description 26
- 125000000217 alkyl group Chemical group 0.000 description 25
- 238000006116 polymerization reaction Methods 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 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
- 125000003118 aryl group Chemical group 0.000 description 19
- 229910052736 halogen Inorganic materials 0.000 description 19
- 150000002367 halogens Chemical class 0.000 description 19
- 229920000642 polymer Polymers 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 16
- 125000000753 cycloalkyl group Chemical group 0.000 description 16
- 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 15
- 125000003342 alkenyl group Chemical group 0.000 description 15
- 230000008859 change Effects 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- 230000000704 physical effect Effects 0.000 description 13
- 239000000178 monomer Substances 0.000 description 12
- 125000003545 alkoxy group Chemical group 0.000 description 11
- 125000002877 alkyl aryl group Chemical group 0.000 description 11
- 125000003710 aryl alkyl group Chemical group 0.000 description 11
- 239000003426 co-catalyst Substances 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000004831 Hot glue Substances 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- 239000012968 metallocene catalyst Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 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 5
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 238000000113 differential scanning calorimetry Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000007774 longterm Effects 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000001291 vacuum drying Methods 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 238000002845 discoloration Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000003780 insertion Methods 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000005234 alkyl aluminium group Chemical group 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 3
- 150000001642 boronic acid derivatives Chemical class 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 229920000092 linear low density polyethylene Polymers 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- OMJKVIFSWSQTGQ-UHFFFAOYSA-N 6,7-bis(aziridin-1-yl)quinazoline-5,8-dione Chemical compound C1CN1C=1C(=O)C2=NC=NC=C2C(=O)C=1N1CC1 OMJKVIFSWSQTGQ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000011954 Ziegler–Natta catalyst Substances 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 125000005131 dialkylammonium group Chemical group 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000004707 linear low-density polyethylene Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 2
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 2
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 2
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 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
- WCFQIFDACWBNJT-UHFFFAOYSA-N $l^{1}-alumanyloxy(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]O[Al] WCFQIFDACWBNJT-UHFFFAOYSA-N 0.000 description 1
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 description 1
- YVSMQHYREUQGRX-UHFFFAOYSA-N 2-ethyloxaluminane Chemical compound CC[Al]1CCCCO1 YVSMQHYREUQGRX-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- JZJDQBZDSBCARL-UHFFFAOYSA-N CC1=C(CC2=C1C1=C(S2)C=CC=C1)C Chemical compound CC1=C(CC2=C1C1=C(S2)C=CC=C1)C JZJDQBZDSBCARL-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-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
- 239000004793 Polystyrene Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000705989 Tetrax Species 0.000 description 1
- 229910003074 TiCl4 Inorganic materials 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 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
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000002902 bimodal effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000000071 blow moulding Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052795 boron group element Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 238000012888 cubic function Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- GNEPOXWQWFSSOU-UHFFFAOYSA-N dichloro-methyl-phenylsilane Chemical compound C[Si](Cl)(Cl)C1=CC=CC=C1 GNEPOXWQWFSSOU-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-O dicyclohexylazanium Chemical compound C1CCCCC1[NH2+]C1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-O 0.000 description 1
- MYBJXSAXGLILJD-UHFFFAOYSA-N diethyl(methyl)alumane Chemical compound CC[Al](C)CC MYBJXSAXGLILJD-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- JGHYBJVUQGTEEB-UHFFFAOYSA-M dimethylalumanylium;chloride Chemical compound C[Al](C)Cl JGHYBJVUQGTEEB-UHFFFAOYSA-M 0.000 description 1
- MWNKMBHGMZHEMM-UHFFFAOYSA-N dimethylalumanylium;ethanolate Chemical compound CCO[Al](C)C MWNKMBHGMZHEMM-UHFFFAOYSA-N 0.000 description 1
- ORVACBDINATSAR-UHFFFAOYSA-N dimethylaluminum Chemical compound C[Al]C ORVACBDINATSAR-UHFFFAOYSA-N 0.000 description 1
- HKUFIYBZNQSHQS-UHFFFAOYSA-O dioctadecylazanium Chemical compound CCCCCCCCCCCCCCCCCC[NH2+]CCCCCCCCCCCCCCCCCC HKUFIYBZNQSHQS-UHFFFAOYSA-O 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- DKQVJMREABFYNT-UHFFFAOYSA-N ethene Chemical compound C=C.C=C DKQVJMREABFYNT-UHFFFAOYSA-N 0.000 description 1
- SHGOGDWTZKFNSC-UHFFFAOYSA-N ethyl(dimethyl)alumane Chemical compound CC[Al](C)C SHGOGDWTZKFNSC-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910021482 group 13 metal Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052752 metalloid Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- CAKOOJUEUVRZLR-UHFFFAOYSA-N methyl(dioctadecyl)phosphane Chemical compound CCCCCCCCCCCCCCCCCCP(C)CCCCCCCCCCCCCCCCCC CAKOOJUEUVRZLR-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- OXQMIXBVXHWDPX-UHFFFAOYSA-N n,n,2-trimethylpropan-2-amine Chemical compound CN(C)C(C)(C)C OXQMIXBVXHWDPX-UHFFFAOYSA-N 0.000 description 1
- 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
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-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
- 230000007935 neutral effect Effects 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical group 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- NDUUEFPGQBSFPV-UHFFFAOYSA-N tri(butan-2-yl)alumane Chemical compound CCC(C)[Al](C(C)CC)C(C)CC NDUUEFPGQBSFPV-UHFFFAOYSA-N 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 1
- PYLGJXLKFZZEBJ-UHFFFAOYSA-N tricyclopentylalumane Chemical compound C1CCCC1[Al](C1CCCC1)C1CCCC1 PYLGJXLKFZZEBJ-UHFFFAOYSA-N 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical compound CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- JOJQVUCWSDRWJE-UHFFFAOYSA-N tripentylalumane Chemical compound CCCCC[Al](CCCCC)CCCCC JOJQVUCWSDRWJE-UHFFFAOYSA-N 0.000 description 1
- JQPMDTQDAXRDGS-UHFFFAOYSA-N triphenylalumane Chemical compound C1=CC=CC=C1[Al](C=1C=CC=CC=1)C1=CC=CC=C1 JQPMDTQDAXRDGS-UHFFFAOYSA-N 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
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- ZMPKTELQGVLZTD-UHFFFAOYSA-N tripropylborane Chemical compound CCCB(CCC)CCC ZMPKTELQGVLZTD-UHFFFAOYSA-N 0.000 description 1
- RERMPCBBVZEPBS-UHFFFAOYSA-N tris(2,6-dimethylphenyl)phosphane Chemical compound CC1=CC=CC(C)=C1P(C=1C(=CC=CC=1C)C)C1=C(C)C=CC=C1C RERMPCBBVZEPBS-UHFFFAOYSA-N 0.000 description 1
- XDSSGQHOYWGIKC-UHFFFAOYSA-N tris(2-methylpropyl)borane Chemical compound CC(C)CB(CC(C)C)CC(C)C XDSSGQHOYWGIKC-UHFFFAOYSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
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Abstract
Description
本出願は、2018年5月4日付韓国特許出願2018−0052045に基づいた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全ての内容は本明細書の一部として含まれる。
以下、本発明のエチレン/アルファ−オレフィン共重合体を詳しく説明する。
本発明の一実施形態によるエチレン/アルファ−オレフィン共重合体は、下記i)からiv)の条件を満たす:
i)粘度:180℃の温度で測定時6,000cPから40,000cP、
ii)分子量分布(MWD):1.5から3.0、
iii)炭素原子1,000個当たりの総不飽和官能基の数:0.8個以下、
iv)下記数式1によるRvd値:0.5以下
i)粘度:180℃の温度で測定時6,000cPから40,000cP、
ii)密度:0.85から0.89g/cc,
iii)分子量分布(MWD):1.5から3.0,
iv)炭素原子1000個当たりの総不飽和官能基の数:0.8個以下、
v)数平均分子量(Mn):9,000から25,000,
vi)ASTM D1238による190℃、2.16kg荷重での溶融指数(MI):200から1,300dg/分、及び
vii)下記数式1によるRvd値:0.5以下
一方、前記のような物性特徴を有するエチレン/アルファ−オレフィン共重合体は、下記化学式1の遷移金属化合物を含む触媒組成物の存在下で、水素を45から100cc/分で投入し、エチレン及びアルファ−オレフィン系単量体を重合する段階を含む製造方法によって製造されてよい。これにより、本発明の他の一実施形態によれば、前記のエチレン/アルファ−オレフィン共重合体の製造方法が提供される:
R2aからR2eは、それぞれ独立して、水素;ハロゲン;炭素数1から20のアルキル;炭素数3から20のシクロアルキル;炭素数2から20のアルケニル;炭素数1から20のアルコキシ;又は炭素数6から20のアリールであり、
R3は、水素;ハロゲン;炭素数1から20のアルキル;炭素数3から20のシクロアルキル;炭素数2から20のアルケニル;炭素数6から20のアリール;炭素数7から20のアルキルアリール;炭素数7から20のアリールアルキル;炭素数1から20のアルキルアミド;又は炭素数6から20のアリールアミド;ハロゲン、炭素数1から20のアルキル、炭素数3から20のシクロアルキル、炭素数2から20のアルケニル、炭素数1から20のアルコキシ及び炭素数6から20のアリールでなる群から選択された1種以上で置換されたフェニルであり、
R4からR9は、それぞれ独立して、水素;シリル;炭素数1から20のアルキル;炭素数3から20のシクロアルキル;炭素数2から20のアルケニル;炭素数6から20のアリール;炭素数7から20のアルキルアリール;炭素数7から20のアリールアルキル;又は炭素数1から20のヒドロカルビルで置換された14族金属のメタロイドラジカルであり;前記R6からR9のうち互いに隣接する2個以上は、互いに連結されて環を形成してよく、
Qは、Si又はCであり、
Mは、4族の遷移金属であり、
X1及びX2は、それぞれ独立して、水素;ハロゲン;炭素数1から20のアルキル;炭素数3から20のシクロアルキル;炭素数2から20のアルケニル;炭素数6から20のアリール;炭素数7から20のアルキルアリール;炭素数7から20のアリールアルキル;炭素数1から20のアルキルアミノ;又は炭素数6から20のアリールアミノである。
より具体的に、前記R3は、水素;炭素数1から12のアルキル;又はフェニルであってよい。
前記R6からR9のうち互いに隣接する2個以上は、互いに連結されて炭素数5から20の脂肪族環又は炭素数6から20の芳香族環を形成してよく;前記脂肪族環又は芳香族環は、ハロゲン、炭素数1から20のアルキル、炭素数2から12のアルケニル、又は炭素数6から12のアリールで置換されてよい。
より具体的に、前記X1及びX2は、それぞれ独立して水素又は炭素数1から12のアルキルであってよい。
R41−[Al(R42)−O]n−R43
前記化学式2において、
R41、R42及びR43は、それぞれ独立して、水素、ハロゲン、炭素数1から20のヒドロカルビル基及びハロゲンで置換された炭素数1から20のヒドロカルビル基のうち何れか一つであり、
nは2以上の整数であり、
[化学式3]
D(R44)3
前記化学式3において、Dはアルミニウム又はホウ素であり、
R44は、それぞれ独立して、ハロゲン、炭素数1から20のヒドロカルビル基、及びハロゲンで置換された炭素数1から20のヒドロカルビル基のうち何れか一つであり、
[化学式4]
[L−H]+[Z(A)4]−又は[L]+[Z(A)4]−
前記化学式4において、
Lは、中性又は陽イオン性ルイス塩基であり、Hは、水素原子であり、
Zは、13族元素であり、Aは、それぞれ独立して、炭素数1から20のヒドロカルビル基;炭素数1から20のヒドロカルビルオキシ基;及びこれら置換基の1以上の水素原子が、ハロゲン、炭素数1から20のヒドロカルビルオキシ基及び炭素数1から20のヒドロカルビルシリル基のうち1以上の置換基で置換された置換基のうち何れか一つである。
段階1:リガンド化合物(1a−1)の製造
250mLのシュレンクフラスコに1,2−ジメチル−3H−ベンゾ[b]シクロペンタ[d]チオフェン10g(1.0eq、49.925mmol)と100mLのTHFを入れ、n−BuLi 22 mL(1.1eq、54.918mmol、2.5M inヘキサン)を−30℃で滴加した後、常温で3時間撹拌した。撹拌したLi−complex THF溶液をジクロロ(メチル)(フェニル)シラン8.1mL(1.0eq、49.925mmol)と70mLのTHFが入っているシュレンクフラスコに−78℃でカニュレーション後、常温で一晩中撹拌した。撹拌してから真空乾燥した後、ヘキサン100mLで抽出した。
100mLのシュレンクフラスコに前記化学式1a−1のリガンド化合物4.93g(12.575mmol、1.0eq)とトルエン50mL(0.2M)を入れ、n−BuLi 10.3mL(25.779mmol、2.05eq、2.5M inヘキサン)を−30℃で滴加した後、常温で一晩中撹拌した。撹拌後にMeMgBr 12.6mL(37.725mmol、3.0 eq、3.0M inジエチルエーテル)を滴加した後、TiCl4 13.2mL(13.204mmol、1.05eq、1.0M inトルエン)を順に入れて常温で一晩中撹拌した。撹拌してから真空乾燥した後、ヘキサン150 mLで抽出し、50mLまで溶媒を除去してからDME 4mL(37.725mmol、3.0eq)を滴加した後、常温で一晩中撹拌した。再び真空乾燥した後、ヘキサン150mLで抽出した。溶媒乾燥してから茶色の固体2.23g(38%、dr=1:0.5)を得た。
実施例1
1.5Lのオートクレーブ連続工程反応器にヘキサン溶媒(5.0kg/h)と1−オクテン(1.00kg/h)を満たした後、反応器上部の温度を150℃に予熱した。トリイソブチルアルミニウム化合物(0.05mmol/分)、触媒として前記合成例で製造した遷移金属化合物(1a)(0.40μmol/分)、ジメチルアニリニウムテトラキス(ペンタフルオロフェニル)ボレート助触媒(1.20μmol/分)を同時に反応器へ投入した。次いで、前記オートクレーブ反応器の中にエチレン(0.87kg/h)及び水素ガス(50cc/分)を投入し、89barの圧力及び重合温度125℃で60分以上維持しながら共重合反応を連続進行して共重合体を製造した。
下記の表1に記載された含量で反応物質を投入することを除いては、前記実施例1と同一の方法で行い重合体を製造した。
実験例1
前記実施例及び比較例で製造したエチレン/アルファ−オレフィン共重合体に対し、下記の方法で物性を測定して表2に示した。
−カラム:PL Olexis
−溶媒:TCB(トリクロロベンゼン;Trichlorobenzene)
−流速:1.0ml/分
−試料濃度:1.0mg/ml
−注入量:200μl
−カラム温度:160℃
−検出器(Detector):Agilent High Temperature RI detector
−標準(Standard):ポリスチレン(Polystyrene)(3次関数で補正)
Claims (9)
- 密度が0.85から0.89g/cc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。
- 重量平均分子量が17,000から40,000g/molである、請求項1又は2に記載のエチレン/アルファ−オレフィン共重合体。
- 粘度が180℃の温度で測定時、8,500から35,000cPである、請求項1〜3のいずれか一項に記載のエチレン/アルファ−オレフィン共重合体。
- 前記数式1によるRvd値が0.3以下である、請求項1〜4のいずれか一項に記載のエチレン/アルファ−オレフィン共重合体。
- 前記アルファ−オレフィンは、プロピレン、1−ブテン、1−ペンテン、4−メチル−1−ペンテン、1−ヘキセン、1−ヘプテン、1−オクテン、1−デセン、1−ウンデセン、1−ドデセン、1−テトラデセン、1−ヘキサデセン及び1−エイコセンで構成される群から選択される1種以上を含む、請求項1〜5のいずれか一項に記載のエチレン/アルファ−オレフィン共重合体。
- 前記アルファ−オレフィンは、1−ブテン、1−ヘキセン及び1−オクテンでなる群から選択される1種以上である、請求項1〜6のいずれか一項に記載のエチレン/アルファ−オレフィン共重合体。
- 前記アルファ−オレフィンは、共重合体の総重量に対して0超過99モル%以下の含量で含まれる、請求項1〜7のいずれか一項に記載のエチレン/アルファ−オレフィン共重合体。
- 下記v)からvii)の条件をさらに満たす、請求項1〜8のいずれか一項に記載のエチレン/アルファ−オレフィン共重合体:
v)炭素原子1000個当たりの総不飽和官能基の数:0.8個以下、
vi)数平均分子量(Mn):9,000から25,000、
vii)ASTM D1238による190℃、2.16kg荷重での溶融指数(MI):200から1,300dg/分。
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CN111788239A (zh) | 2020-10-16 |
EP3747916A1 (en) | 2020-12-09 |
US20210024729A1 (en) | 2021-01-28 |
CN112105655A (zh) | 2020-12-18 |
KR102282281B1 (ko) | 2021-07-27 |
US20210230460A1 (en) | 2021-07-29 |
EP3778669A4 (en) | 2021-07-28 |
CN111788239B (zh) | 2023-08-18 |
EP3778669A1 (en) | 2021-02-17 |
KR102282280B1 (ko) | 2021-07-27 |
JP7276963B2 (ja) | 2023-05-18 |
EP3747916A4 (en) | 2021-04-14 |
KR20190127590A (ko) | 2019-11-13 |
JP2021515828A (ja) | 2021-06-24 |
US11718738B2 (en) | 2023-08-08 |
US11718737B2 (en) | 2023-08-08 |
WO2019212308A1 (ko) | 2019-11-07 |
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