ES2568429T3 - Composiciones azeotrópicas y similares a azeótropos de Z-1,1,1,4,4,4-hexafluoro-2-buteno - Google Patents
Composiciones azeotrópicas y similares a azeótropos de Z-1,1,1,4,4,4-hexafluoro-2-buteno Download PDFInfo
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- ES2568429T3 ES2568429T3 ES09767799.1T ES09767799T ES2568429T3 ES 2568429 T3 ES2568429 T3 ES 2568429T3 ES 09767799 T ES09767799 T ES 09767799T ES 2568429 T3 ES2568429 T3 ES 2568429T3
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Abstract
Una composición que consiste esencialmente en (a) Z-1,1,1,4,4,4-hexafluoro-2-buteno, y (b) un componente seleccionado del grupo que consiste en éter dietílico, 2-cloropropano, y perfluoro(2-metil-3- pentanona); en donde dicho componente está presente en una cantidad eficaz para formar una combinación azeotrópica con el Z-1,1,1,4,4,4-hexafluoro-2-buteno.
Description
ecuación NRTL.
Las temperaturas medidas frente a las composiciones en la celda PTx para la mezcla de Z-FC-1336mzz/éter dietílico se muestran en la figura 1, que ilustra de forma gráfica la formación de una composición azeotrópica o similar a azeótropo que consiste esencialmente en Z-FC-1336mzz y éter dietílico, indicado por una mezcla de 5 aproximadamente 66,8% en moles de Z-1,1,1,4,4,4-hexafluoro-2-buteno y 33,2% en moles de éter dietílico, que tiene la temperatura más baja (aproximadamente 27,5ºC) del intervalo de composiciones a una presión de 83 kPa (12,0 psia). Basándose en estos descubrimientos, se ha calculado que el Z-FC-1336mzz y éter dietílico forman composiciones azeotrópicas en el intervalo de aproximadamente 46,8% en moles a aproximadamente 97,1% en moles de Z-FC-1336mzz y de aproximadamente 2,9% en moles a aproximadamente 53,2% en moles de éter
10 dietílico (que forman composiciones azeotrópicas que hierven a una temperatura de aproximadamente -50ºC a aproximadamente 160ºC y a una presión de aproximadamente 1,4 kPa (0,2 psia) a aproximadamente 2358 kPa (342 psia)). Por ejemplo, a 33,0ºC y presión atmosférica (101 kPa, 14,7 psia) la composición azeotrópica es de 68,8% en moles de Z-1,1,1,4,4,4-hexafluoro-2-buteno y 31,2% en moles de éter dietílico.
Se indican algunas realizaciones de composiciones azeotrópicas en la tabla 1.
15 Tabla 1. Composiciones azeotrópicas: Z-FC-1336mzz y éter dietílico
- Temperatura
- Presión Z-FC-1336mzz Éter dietílico
- ºC
- kPa (psia) Fracción molar Fracción molar
- -50
- 1,24 (0,18) 0,4676 0,5324
- -40
- 2,55 (0,37) 0,4707 0,5293
- -30
- 4,96 (0,72) 0,4854 0,5146
- -20
- 9,03 (1,31) 0,5085 0,4915
- -10
- 15,65 (2,27) 0,5374 0,4626
- 0
- 25,72 (3,73) 0,5701 0,4299
- 10
- 40,61 (5,89) 0,6050 0,3950
- 20
- 61,71 (8,95) 0,6411 0,3589
- 30
- 90,80 (13,17) 0,6775 0,3225
- 40
- 129,90 (18,84) 0,7137 0,2863
- 50
- 181,00 (26,25) 0,7491 0,2509
- 60
- 246,49 (35,75) 0,7833 0,2167
- 70
- 328,95 (47,71) 0,8161 0,1839
- 80
- 431,07 (62,52) 0,8473 0,1527
- 90
- 555,65 (80,59) 0,8765 0,1235
- 100
- 705,95 (102,39) 0,9035 0,0965
- 110
- 885,22 (128,39) 0,9279 0,0721
- 120
- 1097,02 (159,11) 0,9492 0,0508
- 130
- 1345,44 (195,14) 0,9665 0,0335
- 140
- 1634,75 (237,10) 0,9781 0,0219
- 150
- 1969,76 (285,69) 0,9814 0,0186
- 160
- 2356,15 (341,73) 0,9707 0,0293
Además, también se pueden formar composiciones similares a azeótropos que contienen Z-FC-1336mzz y éter dietílico. Dichas composiciones similares a azeótropos existen alrededor de composiciones azeotrópicas. Algunas realizaciones de composiciones similares a azeótropos se indican en la tabla 2. Se indican algunas realizaciones más de composiciones similares a azeótropos en la tabla 3.
- 10
- 46,61 (6,76) 0,4805 0,5195
- 20
- 70,05 (10,16) 0,4992 0,5008
- 30
- 102,04 (14,80) 0,5170 0,4830
- 40
- 144,51 (20,96) 0,5342 0,4658
- 50
- 199,53 (28,94) 0,5512 0,4488
- 60
- 269,31 (39,06) 0,5684 0,4316
- 70
- 356,05 (51,64) 0,5862 0,4138
- 80
- 462,29 (67,05) 0,6051 0,3949
- 90
- 590,47 (85,64) 0,6258 0,3742
- 100
- 743,05 (107,77) 0,6491 0,3509
- 110
- 922,79 (133,84) 0,6762 0,3238
- 120
- 1132,6 (164,27) 0,7087 0,2913
- 130
- 1375,78 (199,54) 0,7491 0,2509
- 150
- 1979,14 (287,05) 0,8747 0,1253
- 160
- 2355,94 (341,70) 0,9870 0,0130
Además, también se pueden formar composiciones similares a azeótropos que contienen Z-FC-1336mzz y 2cloropropano. Dichas composiciones similares a azeótropos existen alrededor de composiciones azeotrópicas. Se indican algunas realizaciones de composiciones similares a azeótropos en la tabla 5. Se indican algunas realizaciones más de composiciones similares a azeótropos en la tabla 6.
Tabla 5. Composiciones similares a azeótropos
- COMPONENTES
- T (ºC) Intervalo de porcentaje molar
- Z-FC-1336mzz/2-cloropropano
- -40 1-4/96-99 17-67/33-83 87-99/1-23
- Z-FC-1336mzz/2-cloropropano
- 0 1-7/93-99 18-99/1-82
- Z-FC-1336mzz/2-cloropropano
- 20 1-99/1-99
- Z-FC-1336mzz/2-cloropropano
- 40 1-99/1-99
- Z-FC-1336mzz/2-cloropropano
- 80 1-99/1-99
- Z-FC-1336mzz/2-cloropropano
- 120 1-99/1-99
- Z-FC-1336mzz/2-cloropropano
- 160 1-99/1-99
Tabla 6. Composiciones similares a azeótropos
- COMPONENTES
- T (ºC) Intervalo de porcentaje molar
- Z-FC-1336mzz/2-cloropropano
- -40 17-67/33-83 87-95/5-23
- Z-FC-1336mzz/2-cloropropano
- 0 18-95/5-82
- Z-FC-1336mzz/2-cloropropano
- 20 10-90/10-90
- Z-FC-1336mzz/2-cloropropano
- 40 10-90/10-90
- Z-FC-1336mzz/2-cloropropano
- 80 10-90/10-90
- Z-FC-1336mzz/2-cloropropano
- 120 10-90/10-90
- Z-FC-1336mzz/2-cloropropano
- 160 10-90/10-90
Se encontró mediante experimentos, que el Z-FC-1336mzz y el perfluoro(2-metil-3-pentanona) forman composiciones azeotrópicas o similares a azeótropos. Para determinar la volatilidad relativa de este par binario, se usó el método PTx descrito antes. Se midió la presión absoluta total en una celda PTx de volumen conocido a temperatura constante, para diferentes composiciones binarias. Estas mediciones después se redujeron a 5 composiciones de vapor y líquido en equilibrio, en la celda usando la ecuación NRTL.
La presión de vapor medida frente a las composiciones en la celda PTx para la mezcla de Z-FC1336mzz/perfluoro(2-metil-3-pentanona) se muestra en la figura 3, que ilustra de forma gráfica la formación de un azeótropo y composiciones similares a azeótropos de Z-1,1,1,4,4,4-hexafluoro-2-buteno y perfluoro(2-metil-3pentanona) a aproximadamente 50ºC, indicado por una mezcla de aproximadamente 82,7% en moles de Z
10 1,1,1,4,4,4-hexafluoro-2-buteno y 17,3% en moles de perfluoro(2-metil-3-pentanona), que tiene la presión más alta (184 kPa (26,7 psia)) del intervalo de composiciones a esta temperatura.
Basándose en estos descubrimientos, se ha calculado que el Z-FC-1336mzz y el perfluoro(2-metil-3-pentanona) forman composiciones azeotrópicas en el intervalo de aproximadamente 68,9% en moles a aproximadamente 87,4% en moles de Z-FC-1336mzz y de aproximadamente 12,6% en moles a aproximadamente 31,1% en moles de
15 perfluoro(2-metil-3-pentanona) (que forman composiciones azeotrópicas que hierven a una temperatura de aproximadamente -50ºC a aproximadamente 140ºC y a una presión de aproximadamente 1,4 kPa (0,2 psia) a aproximadamente 1724 kPa (250 psia). Por ejemplo, a 32,6ºC y presión atmosférica (101 kPa, 14,7 psia) la composición azeotrópica es de 82,6% en moles de Z-1,1,1,4,4,4-hexafluoro-2-buteno y 17,4% en moles de perfluoro(2-metil-3-pentanona).
20 Se indican algunas realizaciones de composiciones azeotrópicas en la tabla 7.
Tabla 7. Composiciones azeotrópicas: Z-FC-1336mzz y Perfluoro(2-metil-3-pentanona)
- Temperatura
- Presión Z-FC-1336mzz Perfluoro(2-metil-3-pentanona)
- ºC
- kPa (psia) Fracción molar Fracción molar
- -50
- 1,17 (0,17) 0,8736 0,1264
- -40
- 2,48 (0,36) 0,8595 0,1405
- -30
- 4,83 (0,70) 0,8483 0,1517
- -20
- 8,96 (1,30) 0,8398 0,1602
- -10
- 15,51 (2,25) 0,8335 0,1665
- 0
- 25,72 (3,73) 0,8293 0,1707
- 10
- 40,75 (5,91) 0,8268 0,1732
- 20
- 62,26 (9,03) 0,8257 0,1743
- 30
- 91,91 (13,33) 0,8257 0,1743
- 40
- 131,69 (19,10) 0,8264 0,1736
- 50
- 183,81 (26,66) 0,8275 0,1725
- 60
- 250,62 (36,35) 0,8286 0,1714
- 70
- 334,74 (48,55) 0,8290 0,1710
- 80
- 438,99 (63,67) 0,8282 0,1718
- 90
- 566,47 (82,16) 0,8255 0,1745
- 100
- 720,71 (104,53) 0,8197 0,1803
- 110
- 905,83 (131,38) 0,8094 0,1906
- 120
- 1127,09 (163,47) 0,7919 0,2081
- 130
- 1392,47 (201,96) 0,7615 0,2385
- 140
- 1721,69 (249,71) 0,6890 0,3110
Además, también se pueden formar composiciones similares a azeótropos que contienen Z-FC-1336mzz y perfluoro(2-metil-3-pentanona). Dichas composiciones similares a azeótropos existen alrededor de composiciones azeotrópicas. Se indican algunas realizaciones de composiciones similares a azeótropos en la tabla 8. Se indican 25 algunas realizaciones más de composiciones similares a azeótropos en la tabla 9.
5
10
15
20
25
30
Tabla 8. Composiciones similares a azeótropos
- COMPONENTES
- T (ºC) Intervalo de porcentaje molar
- Z-FC-1336mzz/perfluoro(2-metil-3-pentanona)
- -40 71-99/1-29
- Z-FC-1336mzz/perfluoro(2-metil-3-pentanona)
- 0 64-99/1-36
- Z-FC-1336mzz/perfluoro(2-metil-3-pentanona)
- 20 61-99/1-39
- Z-FC-1336mzz/perfluoro(2-metil-3-pentanona)
- 40 59-99/1-41
- Z-FC-1336mzz/perfluoro(2-metil-3-pentanona)
- 80 52-99/1-48
- Z-FC-1336mzz/perfluoro(2-metil-3-pentanona)
- 120 42-99/1-58
Tabla 9. Composiciones similares a azeótropos
- COMPONENTES
- T (ºC) Intervalo de porcentaje molar
- Z-FC-1336mzz/perfluoro(2-metil-3-pentanona)
- -40 71-95/5-29
- Z-FC-1336mzz/perfluoro(2-metil-3-pentanona)
- 0 64-95/5-36
- Z-FC-1336mzz/perfluoro(2-metil-3-pentanona)
- 20 61-95/5-39
- Z-FC-1336mzz/perfluoro(2-metil-3-pentanona)
- 40 59-95/5-41
- Z-FC-1336mzz/perfluoro(2-metil-3-pentanona)
- 80 52-95/5-48
- Z-FC-1336mzz/perfluoro(2-metil-3-pentanona)
- 120 42-95/5-58
Las composiciones azeotrópicas o similares a azeótropos de la presente invención se pueden preparar por cualquier método conveniente que incluye la mezcla o combinación de las cantidades deseadas. En una realización de esta invención, una composición azeotrópica o similar a azeótropo se puede preparar pesando las cantidades de los componentes deseados y después combinándolos en una recipiente adecuado.
Las composiciones azeotrópicas o similares a azeótropos de la presente invención se pueden usar en una amplia variedad de aplicaciones, incluyendo su uso como propulsores de aerosoles, disolventes refrigerantes, agentes de limpieza, agentes de soplado (agentes de expansión de espumas) para espumas termoplásticas y termoestables, medios de transferencia de calor, dieléctricos gaseosos, agentes de extinción y supresión de incendios, fluidos de trabajo de ciclos de energía, medios de polimerización, fluidos de eliminación en partículas, fluidos transportadores, agentes abrasivos de pulido, y agentes de secado de desplazamiento.
Una realización de esta invención proporciona un procedimiento para preparar una espuma termoplástica o termoestable. El procedimiento comprende usar una composición azeotrópica o similar a azeótropo como un agente de soplado, en donde dicha composición azeotrópica o similar a azeótropo consiste esencialmente en Z-1,1,1,4,4,4hexafluoro-2-buteno y un componente seleccionado del grupo que consiste en éter dietílico, 2-cloropropano, y perfluoro(2-metil-3-pentanona).
Otra realización de esta invención proporciona un procedimiento para producir refrigeración. El procedimiento comprende condensar una composición azeotrópica o similar a azeótropo y después evaporar dicha composición azeotrópica o similar a azeótropo en las proximidades del cuerpo a enfriar, en donde dicha composición azeotrópica
o similar a azeótropo consiste esencialmente en Z-1,1,1,4,4,4-hexafluoro-2-buteno y un componente seleccionado del grupo que consiste en éter dietílico, 2-cloropropano, y perfluoro(2-metil-3-pentanona).
Otra realización de esta invención proporciona un procedimiento que usa una composición azeotrópica o similar a azeótropo como un disolvente, en donde dicha composición azeotrópica o similar a azeótropo consiste esencialmente en Z-1,1,1,4,4,4-hexafluoro-2-buteno y un componente seleccionado del grupo que consiste en éter dietílico, 2-cloropropano, y perfluoro(2-metil-3-pentanona).
Otra realización de esta invención proporciona un procedimiento para producir un producto en aerosol. El procedimiento comprende usar una composición azeotrópica o similar a azeótropo como un propulsor, en donde dicha composición azeotrópica o similar a azeótropo consiste esencialmente en Z-1,1,1,4,4,4-hexafluoro-2-buteno y un componente seleccionado del grupo que consiste éter dietílico, 2-cloropropano, y perfluoro(2-metil-3-pentanona).
Otra realización de esta invención proporciona un procedimiento que usa una composición azeotrópica o similar a azeótropo como medio de transferencia de calor, en donde dicha composición azeotrópica o similar a azeótropo consiste esencialmente en Z-1,1,1,4,4,4-hexafluoro-2-buteno y un componente seleccionado del grupo que consiste éter dietílico, 2-cloropropano, y perfluoro(2-metil-3-pentanona).
Claims (1)
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imagen1
Applications Claiming Priority (7)
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US74181 | 2008-06-20 | ||
PCT/US2009/047912 WO2009155490A1 (en) | 2008-06-20 | 2009-06-19 | Azeotropic and azeotrope-like compositions of z-1,1,1,4,4,4-hexafluoro-2-butene |
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EP (1) | EP2285930B1 (es) |
JP (3) | JP5806111B2 (es) |
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CN (1) | CN102066521B (es) |
AU (1) | AU2009259965B2 (es) |
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CA (2) | CA2725404A1 (es) |
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MX (1) | MX2010014094A (es) |
PL (1) | PL2285930T3 (es) |
WO (1) | WO2009155490A1 (es) |
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SG176231A1 (en) | 2009-06-02 | 2011-12-29 | Du Pont | Azeotropic and azeotrope-like compositions of z-1,1,1,4,4,4-hexafluoro-2-butene |
US8846754B2 (en) | 2009-12-16 | 2014-09-30 | Honeywell International Inc. | Azeotrope-like compositions of cis-1,1,1,4,4,4-hexafluoro-2-butene |
US20110144216A1 (en) * | 2009-12-16 | 2011-06-16 | Honeywell International Inc. | Compositions and uses of cis-1,1,1,4,4,4-hexafluoro-2-butene |
AU2015234339B2 (en) * | 2009-12-16 | 2017-03-16 | Honeywell International Inc. | Azeotrope-like compositions of cis-1,1,1,4,4,4-hexafluoro-2-butene |
AU2013204160B2 (en) * | 2009-12-16 | 2015-07-02 | Honeywell International Inc. | Azeotrope-like compositions of cis-1,1,1,4,4,4-hexafluoro-2-butene |
US8821749B2 (en) * | 2010-04-26 | 2014-09-02 | E I Du Pont De Nemours And Company | Azeotrope-like compositions of E-1,1,1,4,4,4-hexafluoro-2-butene and 1-chloro-3,3,3-trifluoropropene |
JP6271115B2 (ja) * | 2010-06-11 | 2018-01-31 | 株式会社ダイゾー | エアゾール製品 |
US8066901B1 (en) | 2011-01-19 | 2011-11-29 | Honeywell International Inc. | Azeotrope-like compositions of trans-1,1,1,4,4,4-hexafluoro-2-butene and water |
TWI573971B (zh) | 2011-01-31 | 2017-03-11 | 杜邦股份有限公司 | 使用包含z-1,1,1,4,4,4-六氟-2-丁烯之工作流體製熱 |
CN103517963B (zh) * | 2011-02-04 | 2016-11-09 | 纳幕尔杜邦公司 | 涉及某些卤代烯烃的共沸和类共沸组合物及其用途 |
JP6158182B2 (ja) * | 2011-08-19 | 2017-07-05 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーE.I.Du Pont De Nemours And Company | 熱から機械的エネルギーを発生させるための有機ランキンサイクルのための方法および組成物 |
EP2794806A4 (en) * | 2011-12-22 | 2015-10-14 | Honeywell Int Inc | AZEOTROPÄHNLICHE COMPOSITIONS WITH CIS-1-CHLORO-3,3,3-TRIFLUORPROPEN |
CN104114243A (zh) * | 2012-02-17 | 2014-10-22 | 纳幕尔杜邦公司 | Z-1,1,1,4,4,4-六氟-2-丁烯和e-1,1,1,4,4,4-六氟-2-丁烯的类共沸组合物及其用途 |
WO2016043934A1 (en) * | 2014-09-16 | 2016-03-24 | The Chemours Company Fc, Llc | Azeotropic and azeotrope-like compositions comprising z-1,1,1,4,4,4-hexafluoro-2-butene and methyl perfluoropropyl ether |
CN107207948B (zh) * | 2015-02-06 | 2021-08-06 | 科慕埃弗西有限公司 | 包含z-1,1,1,4,4,4-六氟-2-丁烯的组合物及其用途 |
JP5805345B1 (ja) * | 2015-06-04 | 2015-11-04 | 積水化学工業株式会社 | フェノール樹脂発泡体 |
CN104927775B (zh) * | 2015-07-01 | 2016-08-24 | 西安科技大学 | 煤矿地热利用中的高温热泵混合工质 |
PL3824021T3 (pl) * | 2018-07-16 | 2024-03-04 | The Chemours Company Fc, Llc | Mieszanki środków porotwórczych |
JP2022517068A (ja) * | 2019-01-17 | 2022-03-04 | ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー | (e)-1,1,1,4,4,4-ヘキサフルオロブタ-2-エンの共沸混合物及び共沸混合物様組成物 |
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US5531916A (en) * | 1990-10-03 | 1996-07-02 | E. I. Du Pont De Nemours And Company | Hydrofluorocarbon cleaning compositions |
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TW201815923A (zh) | 2005-06-24 | 2018-05-01 | 美商哈尼威爾國際公司 | 含有經氟取代之烯烴之發泡劑及組合物,及發泡方法 |
US8420706B2 (en) | 2005-06-24 | 2013-04-16 | Honeywell International Inc. | Foaming agents, foamable compositions, foams and articles containing halogen substituted olefins, and methods of making same |
CA2855233A1 (en) * | 2005-11-01 | 2007-05-10 | E.I. Du Pont De Nemours And Company | Blowing agents for forming foam comprising unsaturated fluorocarbons |
US8287752B2 (en) | 2005-11-01 | 2012-10-16 | E I Du Pont De Nemours And Company | Fire extinguishing and fire suppression compositions comprising unsaturated fluorocarbons |
CA3148429A1 (en) | 2005-11-01 | 2007-05-10 | The Chemours Company Fc, Llc | Compositions comprising fluoroolefins and uses thereof |
MY151990A (en) * | 2005-11-01 | 2014-07-31 | Du Pont | Solvent compositions comprising unsaturated fluorinated hydrocarbons |
US7498296B2 (en) | 2006-02-28 | 2009-03-03 | E. I. Dupont De Nemours And Company | Azeotropic compositions comprising fluorinated compounds for cleaning applications |
FR2899233B1 (fr) | 2006-03-31 | 2010-03-12 | Arkema | Composition d'agent d'expansion |
WO2008134061A2 (en) * | 2007-04-27 | 2008-11-06 | E. I. Du Pont De Nemours And Company | Azeotropic and azeotrope-like compositions of z-1,1,1,4,4,4-hexafluoro-2-butene |
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2009
- 2009-06-19 MX MX2010014094A patent/MX2010014094A/es active IP Right Grant
- 2009-06-19 EP EP09767799.1A patent/EP2285930B1/en active Active
- 2009-06-19 KR KR1020117001387A patent/KR101618900B1/ko not_active IP Right Cessation
- 2009-06-19 BR BRPI0909619A patent/BRPI0909619A2/pt not_active IP Right Cessation
- 2009-06-19 JP JP2011514830A patent/JP5806111B2/ja not_active Expired - Fee Related
- 2009-06-19 CN CN2009801233453A patent/CN102066521B/zh active Active
- 2009-06-19 CA CA2725404A patent/CA2725404A1/en not_active Abandoned
- 2009-06-19 WO PCT/US2009/047912 patent/WO2009155490A1/en active Application Filing
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Also Published As
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AU2009259965A1 (en) | 2009-12-23 |
MX2010014094A (es) | 2011-01-21 |
KR101618900B1 (ko) | 2016-05-09 |
CN102066521A (zh) | 2011-05-18 |
WO2009155490A1 (en) | 2009-12-23 |
CO6280546A2 (es) | 2011-05-20 |
AU2009259965B2 (en) | 2015-08-27 |
CA2944302C (en) | 2017-11-21 |
JP2015227467A (ja) | 2015-12-17 |
BRPI0909619A2 (pt) | 2015-09-22 |
KR20110038044A (ko) | 2011-04-13 |
PL2285930T3 (pl) | 2016-07-29 |
JP2014224267A (ja) | 2014-12-04 |
CA2725404A1 (en) | 2009-12-23 |
EP2285930A1 (en) | 2011-02-23 |
CN102066521B (zh) | 2013-11-13 |
JP6051281B2 (ja) | 2016-12-27 |
KR20160040314A (ko) | 2016-04-12 |
JP5957493B2 (ja) | 2016-07-27 |
EP2285930B1 (en) | 2016-01-27 |
JP2011525209A (ja) | 2011-09-15 |
JP5806111B2 (ja) | 2015-11-10 |
CA2944302A1 (en) | 2009-12-23 |
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