RU2015104130A - Способ олигомеризации этилена - Google Patents
Способ олигомеризации этилена Download PDFInfo
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- butene
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- 238000000034 method Methods 0.000 title claims abstract 27
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims abstract 17
- 239000005977 Ethylene Substances 0.000 title claims abstract 17
- 230000003606 oligomerizing effect Effects 0.000 title abstract 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims abstract 32
- 239000003054 catalyst Substances 0.000 claims abstract 8
- 239000000203 mixture Substances 0.000 claims abstract 8
- 239000007788 liquid Substances 0.000 claims abstract 6
- 238000006384 oligomerization reaction Methods 0.000 claims abstract 5
- 239000002904 solvent Substances 0.000 claims abstract 5
- 238000006243 chemical reaction Methods 0.000 claims abstract 2
- 238000010926 purge Methods 0.000 claims abstract 2
- 238000004064 recycling Methods 0.000 claims abstract 2
- 238000000926 separation method Methods 0.000 claims abstract 2
- 239000004711 α-olefin Substances 0.000 claims abstract 2
- 239000011651 chromium Substances 0.000 claims 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims 2
- -1 amino, trimethylsilyl Chemical group 0.000 claims 2
- 150000001845 chromium compounds Chemical class 0.000 claims 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims 2
- 239000003446 ligand Substances 0.000 claims 2
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 claims 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims 2
- WVSBQYMJNMJHIM-UHFFFAOYSA-N (benzene)chromium tricarbonyl Chemical compound [Cr].[O+]#[C-].[O+]#[C-].[O+]#[C-].C1=CC=CC=C1 WVSBQYMJNMJHIM-UHFFFAOYSA-N 0.000 claims 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- JCALBVZBIRXHMQ-UHFFFAOYSA-N [[hydroxy-(phosphonoamino)phosphoryl]amino]phosphonic acid Chemical group OP(O)(=O)NP(O)(=O)NP(O)(O)=O JCALBVZBIRXHMQ-UHFFFAOYSA-N 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 229910052804 chromium Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- MGDOJPNDRJNJBK-UHFFFAOYSA-N ethylaluminum Chemical compound [Al].C[CH2] MGDOJPNDRJNJBK-UHFFFAOYSA-N 0.000 claims 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 229910001502 inorganic halide Inorganic materials 0.000 claims 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims 1
- 239000003607 modifier Substances 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 claims 1
- 125000002524 organometallic group Chemical group 0.000 claims 1
- 125000004437 phosphorous atom Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 claims 1
- 238000005829 trimerization reaction Methods 0.000 claims 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical group C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 238000007599 discharging Methods 0.000 abstract 1
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- 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
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- 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
- C07C2/36—Catalytic processes with hydrides or organic compounds as phosphines, arsines, stilbines or bismuthines
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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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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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- 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
- B01J31/1845—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 phosphorus
- B01J31/1865—Phosphonites (RP(OR)2), their isomeric phosphinates (R2(RO)P=O) and RO-substitution derivatives thereof
- B01J31/187—Amide derivatives thereof
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- 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
- B01J31/1845—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 phosphorus
- B01J31/1885—Ligands comprising two different formal oxidation states of phosphorus in one at least bidentate ligand, e.g. phosphite/phosphinite
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- 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
- C07C2/14—Catalytic processes with inorganic acids; with salts or anhydrides of acids
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Abstract
1. Способ олигомеризации этилена, предусматривающий стадии:a) подачи этилена, растворителя и каталитической композиции, содержащей катализатор и сокатализатор, в реактор,b) олигомеризации этилена в реакторе,c) выгрузки выходящего потока реактора, содержащего линейные альфа-олефины, включая 1-бутен, растворитель, неизрасходованный этилен, растворенный в выходящем потоке реактора, и каталитическую композицию, из реактора,d) отделения этилена и 1-бутена совместно от остального выходящего потока реактора иe) рециркуляции, по меньшей мере, части этилена и 1-бутена, отделенных на стадии d), в реактор.2. Способ по п. 1, в котором рециркулирующий поток этилена и 1-бутена со стадии е) продувают, по меньшей мере, частично при помощи продувочного потока.3. Способ по п. 1 или 2, в котором количество 1-бутена в реакторе составляет по меньшей мере 1 массовый процент, более предпочтительно 5 массовых процентов, более предпочтительно 10 массовых процентов, более предпочтительно 25 массовых процентов, на основе всей массы жидкостей в реакторе.4. Способ по п. 1 или 2, в котором 1-бутен находится в реакторе в максимальном количестве 30 массовых процентов на основе всей массы жидкостей в реакторе.5. Способ по п. 1 или 2, в котором стадию b) проводят при температуре 10-100°С, предпочтительно 30-70°С, и/или давлении приблизительно 10-100 бар.6. Способ по п. 1 или 2, в котором дополнительный 1-бутен подают в реактор из внешнего источника предпочтительно в начальный пусковой период способа олигомеризации.7. Способ по п. 1 или 2, в котором отделение на стадии d) проводят при давлении ниже давления реакции стадии b).8. Способ по п. 1 или 2, в котором этилен и 1-бутен рециркулируют в реактор в жидкой форме.9. Способ по п. 1 или 2, который представляет собой
Claims (15)
1. Способ олигомеризации этилена, предусматривающий стадии:
a) подачи этилена, растворителя и каталитической композиции, содержащей катализатор и сокатализатор, в реактор,
b) олигомеризации этилена в реакторе,
c) выгрузки выходящего потока реактора, содержащего линейные альфа-олефины, включая 1-бутен, растворитель, неизрасходованный этилен, растворенный в выходящем потоке реактора, и каталитическую композицию, из реактора,
d) отделения этилена и 1-бутена совместно от остального выходящего потока реактора и
e) рециркуляции, по меньшей мере, части этилена и 1-бутена, отделенных на стадии d), в реактор.
2. Способ по п. 1, в котором рециркулирующий поток этилена и 1-бутена со стадии е) продувают, по меньшей мере, частично при помощи продувочного потока.
3. Способ по п. 1 или 2, в котором количество 1-бутена в реакторе составляет по меньшей мере 1 массовый процент, более предпочтительно 5 массовых процентов, более предпочтительно 10 массовых процентов, более предпочтительно 25 массовых процентов, на основе всей массы жидкостей в реакторе.
4. Способ по п. 1 или 2, в котором 1-бутен находится в реакторе в максимальном количестве 30 массовых процентов на основе всей массы жидкостей в реакторе.
5. Способ по п. 1 или 2, в котором стадию b) проводят при температуре 10-100°С, предпочтительно 30-70°С, и/или давлении приблизительно 10-100 бар.
6. Способ по п. 1 или 2, в котором дополнительный 1-бутен подают в реактор из внешнего источника предпочтительно в начальный пусковой период способа олигомеризации.
7. Способ по п. 1 или 2, в котором отделение на стадии d) проводят при давлении ниже давления реакции стадии b).
8. Способ по п. 1 или 2, в котором этилен и 1-бутен рециркулируют в реактор в жидкой форме.
9. Способ по п. 1 или 2, который представляет собой тримеризацию.
10. Способ по по п. 1, в котором каталитическая композиция содержит катализатор, содержащий соединение хрома и лиганд общей структуры (A) R1R2P-N(R3)-P(R4)-N(R5)-H или (В) R1R2P-N(R3)-P(R4)-N(R5)-PR6R7, где R1-R7 независимо выбирают из галогена, амино, триметилсилила, С1-С10-алкила, С6-С20-арила или любых циклических производных (А) или (В), где по меньшей мере один из атомов Р или N PNPN-звена или PNPNP-звена представляет собой член кольцевой системы, причем кольцевая система образована из одного или нескольких составляющих соединений структур (А) или (В) путем замещения.
11. Способ по п. 10, в котором соединение хрома выбирают из органических или неорганических солей, координационных комплексов и металлорганических комплексов Cr (II) или Cr (III), предпочтительно CrCl3(THF)3, ацетилацетоната Cr (III), октаноата Cr (III), гексакарбонила хрома, Cr (III)-2-этилгексаноата, бензол(трикарбонил)-хрома или хлорида Cr (III).
12. Способ по любому из пп. 1 или 2, 10 или 11, в котором сокатализатор выбирают из триметилалюминия, триэтилалюминия, триизопропилалюминия, триизобутилалюминия, полуторного хлорида этилалюминия, хлорида диэтилалюминия, дихлорида этилалюминия, метилалюмоксана (МАО) или их смесей.
13. Способ по любому из пп. 1 или 2, 10 или 11, в котором каталитическая композиция дополнительно содержит модификатор, содержащий органический или неорганический галогенид.
14. Способ по любому из пп. 10 или 11, в котором лиганд выбирают из Ph2P-N(i-Pr)-P(Ph)-N(i-Pr)-H, Ph2P-N(i-Pr)-P(Ph)-N(Ph)-H, Ph2P-N(i-Pr)-P(Ph)-N(трет-бутил)-Н и Ph2P-N(i-Pr)-P(Ph)-N(CH(CH3)(Ph))-H.
15. Способ по любому из пп. 1 или 2, 10 или 11, в котором растворитель выбирают из ароматических углеводородов, с прямой цепью и циклических алифатических углеводородов и эфиров, предпочтительно толуола, бензола, этилбензола, кумола, ксилола, мезитилена, гексана, октана, циклогексана, метилциклогексана, диэтилового эфира, тетрагидрофурана и их смесей, наиболее предпочтительно толуола.
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EP12175732.2 | 2012-07-10 | ||
EP12175732.2A EP2684857A1 (en) | 2012-07-10 | 2012-07-10 | Method for oligomerization of ethylene |
PCT/EP2013/001658 WO2014008964A1 (en) | 2012-07-10 | 2013-06-05 | Method for oligomerization of ethylene |
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US (1) | US9896392B2 (ru) |
EP (2) | EP2684857A1 (ru) |
JP (1) | JP6081590B2 (ru) |
KR (1) | KR101719221B1 (ru) |
CN (1) | CN104661989B (ru) |
BR (1) | BR112015000387B1 (ru) |
CA (1) | CA2878634C (ru) |
ES (1) | ES2651154T3 (ru) |
IN (1) | IN2014DN10972A (ru) |
MX (1) | MX362715B (ru) |
RU (1) | RU2616602C2 (ru) |
SG (1) | SG11201408518WA (ru) |
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WO (1) | WO2014008964A1 (ru) |
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-
2012
- 2012-07-10 EP EP12175732.2A patent/EP2684857A1/en not_active Withdrawn
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2013
- 2013-06-05 JP JP2015520830A patent/JP6081590B2/ja not_active Expired - Fee Related
- 2013-06-05 ES ES13727521.0T patent/ES2651154T3/es active Active
- 2013-06-05 BR BR112015000387-7A patent/BR112015000387B1/pt not_active IP Right Cessation
- 2013-06-05 CN CN201380035491.7A patent/CN104661989B/zh not_active Expired - Fee Related
- 2013-06-05 IN IN10972DEN2014 patent/IN2014DN10972A/en unknown
- 2013-06-05 US US14/414,403 patent/US9896392B2/en not_active Expired - Fee Related
- 2013-06-05 SG SG11201408518WA patent/SG11201408518WA/en unknown
- 2013-06-05 WO PCT/EP2013/001658 patent/WO2014008964A1/en active Application Filing
- 2013-06-05 MX MX2015000216A patent/MX362715B/es active IP Right Grant
- 2013-06-05 CA CA2878634A patent/CA2878634C/en not_active Expired - Fee Related
- 2013-06-05 KR KR1020157003434A patent/KR101719221B1/ko active IP Right Grant
- 2013-06-05 RU RU2015104130A patent/RU2616602C2/ru active
- 2013-06-05 EP EP13727521.0A patent/EP2872468B1/en not_active Not-in-force
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KR101719221B1 (ko) | 2017-03-23 |
CA2878634C (en) | 2019-07-16 |
KR20150043313A (ko) | 2015-04-22 |
EP2872468B1 (en) | 2017-11-15 |
JP6081590B2 (ja) | 2017-02-15 |
US20150203418A1 (en) | 2015-07-23 |
JP2015527311A (ja) | 2015-09-17 |
WO2014008964A8 (en) | 2015-02-19 |
BR112015000387A2 (pt) | 2017-06-27 |
MX2015000216A (es) | 2015-04-10 |
EP2684857A1 (en) | 2014-01-15 |
MX362715B (es) | 2019-01-25 |
TW201406704A (zh) | 2014-02-16 |
WO2014008964A1 (en) | 2014-01-16 |
SG11201408518WA (en) | 2015-02-27 |
IN2014DN10972A (ru) | 2015-09-18 |
BR112015000387A8 (pt) | 2019-02-19 |
CN104661989A (zh) | 2015-05-27 |
TWI582063B (zh) | 2017-05-11 |
RU2616602C2 (ru) | 2017-04-18 |
US9896392B2 (en) | 2018-02-20 |
BR112015000387B1 (pt) | 2020-11-10 |
CA2878634A1 (en) | 2014-01-16 |
CN104661989B (zh) | 2018-05-22 |
EP2872468A1 (en) | 2015-05-20 |
ES2651154T3 (es) | 2018-01-24 |
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