ES2620287T3 - Complejos de guanidinato y su uso como catalizadores de polimerización de transferencia de cadenas - Google Patents
Complejos de guanidinato y su uso como catalizadores de polimerización de transferencia de cadenas Download PDFInfo
- Publication number
- ES2620287T3 ES2620287T3 ES12004263.5T ES12004263T ES2620287T3 ES 2620287 T3 ES2620287 T3 ES 2620287T3 ES 12004263 T ES12004263 T ES 12004263T ES 2620287 T3 ES2620287 T3 ES 2620287T3
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- Prior art keywords
- phenyl
- catalyst
- ortho
- oxygen
- alcohols
- Prior art date
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- 238000012711 chain transfer polymerization Methods 0.000 title description 3
- 239000002685 polymerization catalyst Substances 0.000 title description 3
- 239000003054 catalyst Substances 0.000 claims abstract description 51
- 239000000203 mixture Substances 0.000 claims abstract description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 29
- 229910052751 metal Inorganic materials 0.000 claims abstract description 23
- 239000002184 metal Substances 0.000 claims abstract description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000001301 oxygen Substances 0.000 claims abstract description 22
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000003446 ligand Substances 0.000 claims abstract description 15
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 9
- 150000004696 coordination complex Chemical class 0.000 claims abstract description 8
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 7
- -1 t-butyl phenyl Chemical group 0.000 claims description 48
- 239000003426 co-catalyst Substances 0.000 claims description 45
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 42
- 239000005977 Ethylene Substances 0.000 claims description 42
- 229920000642 polymer Polymers 0.000 claims description 32
- 229910052782 aluminium Inorganic materials 0.000 claims description 31
- 239000012190 activator Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 21
- 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 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 17
- 229910052723 transition metal Inorganic materials 0.000 claims description 16
- 239000011701 zinc Substances 0.000 claims description 16
- 150000001298 alcohols Chemical class 0.000 claims description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- 150000003624 transition metals Chemical class 0.000 claims description 14
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 13
- 229910052725 zinc Inorganic materials 0.000 claims description 13
- 239000002243 precursor Substances 0.000 claims description 11
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 10
- 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 claims description 9
- 229910052726 zirconium Inorganic materials 0.000 claims description 9
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical group [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 8
- 150000001336 alkenes Chemical class 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 150000004678 hydrides Chemical class 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 7
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 7
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- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 238000011065 in-situ storage Methods 0.000 claims description 5
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
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- 230000007062 hydrolysis Effects 0.000 claims description 4
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- OJJVPGJEBAZOIF-UHFFFAOYSA-N (2,3,4,5-tetrafluorophenoxy)boronic acid Chemical compound OB(O)OC1=CC(F)=C(F)C(F)=C1F OJJVPGJEBAZOIF-UHFFFAOYSA-N 0.000 claims 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- NPHLURKGGOFSPO-UHFFFAOYSA-N tris(2,3,4,5-tetrafluorophenyl)borane Chemical compound FC1=C(F)C(F)=CC(B(C=2C(=C(F)C(F)=C(F)C=2)F)C=2C(=C(F)C(F)=C(F)C=2)F)=C1F NPHLURKGGOFSPO-UHFFFAOYSA-N 0.000 claims 1
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 claims 1
- 150000003752 zinc compounds Chemical class 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 106
- 238000006116 polymerization reaction Methods 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 27
- 239000000047 product Substances 0.000 description 17
- 238000007254 oxidation reaction Methods 0.000 description 15
- 230000003647 oxidation Effects 0.000 description 14
- 239000010936 titanium Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 9
- 230000003197 catalytic effect Effects 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000012546 transfer Methods 0.000 description 8
- ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 description 7
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 150000002170 ethers Chemical class 0.000 description 7
- 229940052303 ethers for general anesthesia Drugs 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 229910052719 titanium Inorganic materials 0.000 description 7
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000012986 chain transfer agent Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 6
- XLDBGFGREOMWSL-UHFFFAOYSA-N n,n'-bis[2,6-di(propan-2-yl)phenyl]methanediimine Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N=C=NC1=C(C(C)C)C=CC=C1C(C)C XLDBGFGREOMWSL-UHFFFAOYSA-N 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 239000001993 wax Substances 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 238000003379 elimination reaction Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000012041 precatalyst Substances 0.000 description 5
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 4
- 125000003368 amide group Chemical group 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-O diethylammonium Chemical compound CC[NH2+]CC HPNMFZURTQLUMO-UHFFFAOYSA-O 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-O dimethyl(phenyl)azanium Chemical compound C[NH+](C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-O 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
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- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
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- 238000005481 NMR spectroscopy Methods 0.000 description 3
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- 125000005234 alkyl aluminium group Chemical group 0.000 description 3
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- 239000013078 crystal Substances 0.000 description 3
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
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- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 3
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 3
- WYXIGTJNYDDFFH-UHFFFAOYSA-Q triazanium;borate Chemical compound [NH4+].[NH4+].[NH4+].[O-]B([O-])[O-] WYXIGTJNYDDFFH-UHFFFAOYSA-Q 0.000 description 3
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 3
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- 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 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- JBKVKRHXJZYMTE-UHFFFAOYSA-N 2,3-bis[2,6-di(propan-2-yl)phenyl]-1,1-diethylguanidine Chemical compound CCN(CC)C(Nc1c(cccc1C(C)C)C(C)C)=N/c1c(cccc1C(C)C)C(C)C JBKVKRHXJZYMTE-UHFFFAOYSA-N 0.000 description 2
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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- 125000004122 cyclic group Chemical group 0.000 description 2
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- KVBQLZFARKMMEZ-UHFFFAOYSA-N [Zr+6] Chemical compound [Zr+6] KVBQLZFARKMMEZ-UHFFFAOYSA-N 0.000 description 1
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
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- NTBYNMBEYCCFPS-UHFFFAOYSA-N azane boric acid Chemical class N.N.N.OB(O)O NTBYNMBEYCCFPS-UHFFFAOYSA-N 0.000 description 1
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- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
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- PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 1
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- 125000005131 dialkylammonium group Chemical group 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-O dicyclohexylazanium Chemical compound C1CCCCC1[NH2+]C1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-O 0.000 description 1
- 229960004132 diethyl ether Drugs 0.000 description 1
- HJXBDPDUCXORKZ-UHFFFAOYSA-N diethylalumane Chemical compound CC[AlH]CC HJXBDPDUCXORKZ-UHFFFAOYSA-N 0.000 description 1
- UAGOIYVTYUSMIF-UHFFFAOYSA-N dimethyl-(2,3,4,5,6-pentafluorophenyl)-[2,3,4-tris(2,3,4,5,6-pentafluorophenyl)phenyl]azanium borate Chemical compound B([O-])([O-])[O-].FC1=C(C(=C(C(=C1C1=C(C(=C([N+](C)(C)C2=C(C(=C(C(=C2F)F)F)F)F)C=C1)C1=C(C(=C(C(=C1F)F)F)F)F)C1=C(C(=C(C(=C1F)F)F)F)F)F)F)F)F.FC1=C(C(=C(C(=C1C1=C(C(=C([N+](C2=C(C(=C(C(=C2F)F)F)F)F)(C)C)C=C1)C1=C(C(=C(C(=C1F)F)F)F)F)C1=C(C(=C(C(=C1F)F)F)F)F)F)F)F)F.FC1=C(C(=C(C(=C1C1=C(C(=C([N+](C2=C(C(=C(C(=C2F)F)F)F)F)(C)C)C=C1)C1=C(C(=C(C(=C1F)F)F)F)F)C1=C(C(=C(C(=C1F)F)F)F)F)F)F)F)F UAGOIYVTYUSMIF-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 1
- NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical class CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 150000002362 hafnium Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- NRQNMMBQPIGPTB-UHFFFAOYSA-N methylaluminum Chemical compound [CH3].[Al] NRQNMMBQPIGPTB-UHFFFAOYSA-N 0.000 description 1
- PVSYUABXYMZSHY-UHFFFAOYSA-N n'-[2,6-di(propan-2-yl)phenyl]benzenecarboximidamide Chemical compound CC(C)C1=CC=CC(C(C)C)=C1NC(=N)C1=CC=CC=C1 PVSYUABXYMZSHY-UHFFFAOYSA-N 0.000 description 1
- ASCJVQUJOIYDBI-UHFFFAOYSA-N n,n'-bis(2-methoxyphenyl)methanediimine Chemical compound COC1=CC=CC=C1N=C=NC1=CC=CC=C1OC ASCJVQUJOIYDBI-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
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- 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 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 150000003608 titanium Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- ANEFWEBMQHRDLH-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl) borate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1OB(OC=1C(=C(F)C(F)=C(F)C=1F)F)OC1=C(F)C(F)=C(F)C(F)=C1F ANEFWEBMQHRDLH-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
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- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
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- B01J31/122—Metal aryl or alkyl compounds
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
- B01J31/143—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron of aluminium
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- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/26—Catalytic processes with hydrides or organic compounds
- C07C2/32—Catalytic processes with hydrides or organic compounds as complexes, e.g. acetyl-acetonates
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
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- C07C31/20—Dihydroxylic alcohols
- C07C31/202—Ethylene glycol
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
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- C07C31/20—Dihydroxylic alcohols
- C07C31/205—1,3-Propanediol; 1,2-Propanediol
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/003—Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/28—Titanium compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
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- B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
- B01J2231/12—Olefin polymerisation or copolymerisation
- B01J2231/122—Cationic (co)polymerisation, e.g. single-site or Ziegler-Natta type
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- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/46—C-H or C-C activation
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- B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
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- B01J2231/76—Dehydrogenation
- B01J2231/766—Dehydrogenation of -CH-CH- or -C=C- to -C=C- or -C-C- triple bond species
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/001—General concepts, e.g. reviews, relating to catalyst systems and methods of making them, the concept being defined by a common material or method/theory
- B01J2531/002—Materials
- B01J2531/007—Promoter-type Additives
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
- B01J2531/46—Titanium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
- B01J2531/48—Zirconium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
- B01J2531/49—Hafnium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/22—Organic complexes
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/52—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides selected from boron, aluminium, gallium, indium, thallium or rare earths
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12004263.5A EP2671639B1 (en) | 2012-06-04 | 2012-06-04 | Guanidinate complexes and their use as chain transfer polymerization catalysts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2620287T3 true ES2620287T3 (es) | 2017-06-28 |
Family
ID=48570057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES12004263.5T Active ES2620287T3 (es) | 2012-06-04 | 2012-06-04 | Complejos de guanidinato y su uso como catalizadores de polimerización de transferencia de cadenas |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9579640B2 (enExample) |
| EP (2) | EP2671639B1 (enExample) |
| JP (1) | JP2015525268A (enExample) |
| CN (1) | CN104349840A (enExample) |
| BR (1) | BR112014030113A2 (enExample) |
| CA (1) | CA2874682A1 (enExample) |
| ES (1) | ES2620287T3 (enExample) |
| PL (1) | PL2671639T3 (enExample) |
| RU (1) | RU2014149897A (enExample) |
| WO (1) | WO2013182290A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2857423B1 (en) * | 2013-10-07 | 2020-09-16 | Arlanxeo Netherlands B.V. | Catalyst system |
| BR112016012971B1 (pt) * | 2013-12-19 | 2021-06-08 | Dow Global Technologies Llc | complexo de metal-ligante, catalisador e processo para preparar uma poliolefina |
| EP3037437A1 (en) * | 2014-12-23 | 2016-06-29 | SABIC Global Technologies B.V. | Process for the preparation of a polyolefin having one or multiple end-functionalized branches. |
| EP3093280A1 (en) | 2015-05-13 | 2016-11-16 | Sasol Performance Chemicals GmbH | Process for the oligomerisation of olefins by coordinative chain transfer polymerisation and catalyst synthesis |
| WO2016180539A1 (en) * | 2015-05-13 | 2016-11-17 | Sasol Performance Chemicals Gmbh | PROCESS FOR THE MANUFACTURE OF A ZIRCONIUM GUANIDINATO ALKYL COMPOUND AND A DI-μ-HALOGEN-BRIDGED BIS GUANIDINATO TETRAHALOGEN DI ZIRCONIUM COMPOUND |
| CN104857989B (zh) * | 2015-05-27 | 2017-03-01 | 山西大学 | 一种双胍基铝金属催化剂及其制备方法和应用 |
| JP6916808B2 (ja) * | 2016-03-31 | 2021-08-11 | ダウ グローバル テクノロジーズ エルエルシー | オレフィン重合触媒 |
| US11939137B2 (en) | 2018-11-30 | 2024-03-26 | Dow Global Technologies Llc | Flexible container with dispensing pump |
| SG11202112062PA (en) | 2019-05-31 | 2021-11-29 | Dow Global Technologies Llc | Monobindentate, bis-bidentate, and tetrabidentate guanidine group iv transition metal olefin copolymerization catalysts |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3419352A (en) | 1964-12-02 | 1968-12-31 | Continental Oil Co | Process for producing alpha alumina monohydrate |
| US3641085A (en) | 1969-05-01 | 1972-02-08 | Continental Oil Co | Oxidation of aluminum alkyls |
| US3660447A (en) | 1969-07-18 | 1972-05-02 | Ethyl Corp | Process of oxidizing aluminum alkyls |
| US5153157A (en) | 1987-01-30 | 1992-10-06 | Exxon Chemical Patents Inc. | Catalyst system of enhanced productivity |
| PL276385A1 (en) | 1987-01-30 | 1989-07-24 | Exxon Chemical Patents Inc | Method for polymerization of olefines,diolefins and acetylene unsaturated compounds |
| EP0329891A2 (en) | 1988-02-23 | 1989-08-30 | Petrolite Corporation | End-functionalized low molecular weight polymers of ethylene |
| US5043515A (en) * | 1989-08-08 | 1991-08-27 | Shell Oil Company | Ethylene oligomerization catalyst and process |
| US5064802A (en) | 1989-09-14 | 1991-11-12 | The Dow Chemical Company | Metal complex compounds |
| JP2545006B2 (ja) | 1990-07-03 | 1996-10-16 | ザ ダウ ケミカル カンパニー | 付加重合触媒 |
| US5721185A (en) | 1991-06-24 | 1998-02-24 | The Dow Chemical Company | Homogeneous olefin polymerization catalyst by abstraction with lewis acids |
| US5502128A (en) | 1994-12-12 | 1996-03-26 | University Of Massachusetts | Group 4 metal amidinate catalysts and addition polymerization process using same |
| FI102476B1 (fi) | 1996-05-31 | 1998-12-15 | Borealis As | Uudet siirtymämetallikompleksit ja menetelmä niiden valmistamiseksi |
| JP3588665B2 (ja) * | 1996-06-04 | 2004-11-17 | 東ソー株式会社 | 遷移金属錯体を用いたオレフィン重合触媒およびそれを用いたポリオレフィンの製造法 |
| US5777120A (en) | 1997-03-14 | 1998-07-07 | University Of Iowa Research Foundation | Cationic aluminum alkyl complexes incorporating amidinate ligands as polymerization catalysts |
| US7589150B2 (en) * | 2000-12-12 | 2009-09-15 | Baker Hughes Incorporated | Low molecular weight isotactic polypropylene polymers, copolymers and derivatives and materials prepared therewith |
| DE102004030080A1 (de) * | 2004-06-22 | 2006-01-12 | Sasol Germany Gmbh | Verfahren zur Herstellung primärer langkettiger Alkohole |
| US20100209610A1 (en) * | 2007-07-16 | 2010-08-19 | Advanced Technology Materials, Inc. | Group iv complexes as cvd and ald precursors for forming metal-containing thin films |
| CN102432700A (zh) | 2011-09-01 | 2012-05-02 | 山西大学 | 桥联双脒基钛金属催化剂及其制备方法和应用 |
| US20130131294A1 (en) * | 2011-11-21 | 2013-05-23 | John R. Hagadorn | Amidinate Catalyst Compounds, Process for Their Use and Polymers Produced Therefrom |
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2012
- 2012-06-04 ES ES12004263.5T patent/ES2620287T3/es active Active
- 2012-06-04 PL PL12004263T patent/PL2671639T3/pl unknown
- 2012-06-04 EP EP12004263.5A patent/EP2671639B1/en not_active Not-in-force
-
2013
- 2013-06-03 US US14/405,505 patent/US9579640B2/en not_active Expired - Fee Related
- 2013-06-03 WO PCT/EP2013/001614 patent/WO2013182290A1/en not_active Ceased
- 2013-06-03 CA CA2874682A patent/CA2874682A1/en not_active Abandoned
- 2013-06-03 CN CN201380029386.2A patent/CN104349840A/zh active Pending
- 2013-06-03 EP EP13726429.7A patent/EP2855015A1/en not_active Withdrawn
- 2013-06-03 JP JP2015515416A patent/JP2015525268A/ja active Pending
- 2013-06-03 RU RU2014149897A patent/RU2014149897A/ru not_active Application Discontinuation
- 2013-06-03 BR BR112014030113A patent/BR112014030113A2/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2015525268A (ja) | 2015-09-03 |
| US9579640B2 (en) | 2017-02-28 |
| US20150148505A1 (en) | 2015-05-28 |
| RU2014149897A (ru) | 2016-08-10 |
| PL2671639T3 (pl) | 2017-07-31 |
| BR112014030113A2 (pt) | 2017-06-27 |
| EP2671639A1 (en) | 2013-12-11 |
| EP2855015A1 (en) | 2015-04-08 |
| CA2874682A1 (en) | 2013-12-12 |
| CN104349840A (zh) | 2015-02-11 |
| EP2671639B1 (en) | 2017-01-11 |
| WO2013182290A1 (en) | 2013-12-12 |
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