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WO2009118189A1 - Échange basique pour des matériaux de stockage d'oxygène (os) redox évolués destinés à des applications de contrôle des émissions - Google Patents

Échange basique pour des matériaux de stockage d'oxygène (os) redox évolués destinés à des applications de contrôle des émissions Download PDF

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Publication number
WO2009118189A1
WO2009118189A1 PCT/EP2009/002262 EP2009002262W WO2009118189A1 WO 2009118189 A1 WO2009118189 A1 WO 2009118189A1 EP 2009002262 W EP2009002262 W EP 2009002262W WO 2009118189 A1 WO2009118189 A1 WO 2009118189A1
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Prior art keywords
metal
oxide
phase
solution
redox
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PCT/EP2009/002262
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English (en)
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WO2009118189A4 (fr
Inventor
Barry W. L. Southward
Curt Ellis
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Umicore Ag & Co. Kg
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Priority claimed from US12/240,170 external-priority patent/US20090246109A1/en
Priority claimed from US12/363,310 external-priority patent/US9403151B2/en
Priority claimed from US12/363,329 external-priority patent/US20100196217A1/en
Application filed by Umicore Ag & Co. Kg filed Critical Umicore Ag & Co. Kg
Priority to CN2009801108862A priority Critical patent/CN101980778A/zh
Priority to JP2011501154A priority patent/JP2011526197A/ja
Priority to EP09723698.8A priority patent/EP2268394A1/fr
Priority to BRPI0909381A priority patent/BRPI0909381A2/pt
Publication of WO2009118189A1 publication Critical patent/WO2009118189A1/fr
Publication of WO2009118189A4 publication Critical patent/WO2009118189A4/fr

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Definitions

  • Oxygen Storage (OS) materials are well known solid electrolytes based on, for example, Ceria-Zirconia (CeO 2 -ZrO 2 ) solid solutions. They are a ubiquitous component of aftertreatment catalysts for gasoline vehicles due to their ability to 'buffer' the active components in the catalyst against local fuel rich (reducing) or fuel lean (oxidising) conditions. OS materials do this by releasing active oxygen from their 3-D structure in a rapid and reproducible manner under oxygen-depleted transients, regenerating this 'lost' oxygen by adsorption from the gaseous phase when oxygen rich conditions arise.
  • This reduction-oxidation (hereafter redox) chemistry is attributed to the Ce 4+ ⁇ -» Ce 3+ redox couple, with the oxidation state of Ce depending upon local O 2 content.
  • This high availability of oxygen is critical for the promotion of generic oxidation / reduction chemistries e.g. CO / NO chemistry for the gasoline three-way catalyst, or more recently for the direct catalytic oxidation of particulate matter (soot) in the catalysed diesel particulate filter (CDPF) e.g. US2005 0282698 Al.
  • a further, and perhaps more significant, drawback of introducing low valent base metal ions within the Cubic Fluorite lattice is that the ions are dispersed throughout the bulk of the crystal structure and thus the surface concentration of the ions may be very low. This in turn limits the extent of the dopant ions to interact directly with the exhaust environment.
  • the ability of these ions to provide additional chemical functionality e.g. as a NOx trap to provide transient adsorption of NO and NO 2 is limited by the available concentrations of ions in the surface and immediate subsurface of the crystal.
  • the basic ion exchange process is a discrete, post-synthetic modification and hence provides for markedly higher flexibility of composition, dopant ion type and concentration as compared to conventional direct synthetic methods as described in previous work (US 6,468,941 and US 6,585,944).
  • the resultant materials demonstrate high activity and hydrothermal durability under all aging conditions examined. This is in contrast to promotion that may be realised by conventional impregnation of an acidic metal e.g. metal nitrate where formation of bulk oxide phases in fresh materials and rapid sintering of such oxide phases, with resultant deactivation, is the norm.
  • an acidic metal e.g. metal nitrate where formation of bulk oxide phases in fresh materials and rapid sintering of such oxide phases, with resultant deactivation, is the norm.
  • the method developed provides a wide, and novel, range of materials of stable and highly active
  • OS materials that may be advantageously applied to a wide range of emission control applications for both gasoline and diesel vehicles.
  • the method of this invention enables choice and tailoring of the base metal promotant to introduce specific chemical synergies to incorporate or enhance additional catalytic functions, e.g. lean NOx control.
  • high redox activity can be obtained by the modification of solid solutions based on Ce-ZrOx by a mechanism which is proposed, while not wishing to be bound by theory, to involve the basic/alkaline exchange of the pre-existing Ce-OH hydroxyl defect sites that exist within all OS materials.
  • the Ce-OH sites are believed to arise at Ce 3+ defect sites within the lattice and the presence of the proton of the hydroxyl group being a requirement for electrical neutrality of the lattice.
  • the proposed exchange of the H + atom by metal ions enables the incorporation and stabilisation of specific mono-valent (e.g. K + ), di-valent (e.g. Cu 2+ ), tri- valent (e.g.
  • base metals to be incorporated within the mixed oxide in this manner can additionally be based upon oxides known to be active for reactions of especial interest or catalytic importance. Examples include, but are not limited to, direct catalytic soot oxidation, low temperature SCR (Selective Catalytic Reduction by urea, NH 3 or hydrocarbons), NOx trapping, low temperature CO-NO or CO-O 2 reaction promoters, hydrocarbon cracking function (e.g. by increasing the acidity of the OS), etc.
  • Metals appropriate to these examples include Ag, Cu, Co, Mn, Fe, alkali metals, alkaline earth metals or transitions metals, or other metal or metalloid known to form a stable nitrate which can undergo subsequent decomposition and reduction N 2 under conditions within the conventional operational window of the vehicle exhaust.
  • transition metal means the 38 elements in Groups 3 to 12 of the Periodic Table of Elements.
  • the association of the promotant occurs post-synthesis, and while not wishing to be bound by theory, via a specific ion exchange mechanism and the ions thus introduced and incorporated in a range of sites associated with the Ce 3+ -OH defects and not in any well defined and unique cationic position.
  • the method of the present invention enables the introduction of higher concentrations of the base metal ions / oxide component since the loading is not limited by its solubility within a well- defined mixed oxide matrix of phase purity.
  • the loading of effective promotant is limited by the concentration of structural hydroxls within the lattice as are typically associated with point defects or surface terminations of primary crystals.
  • Ce in the catalytic oxidation of CO for example is based upon its redox activity as follows: Ce 3+ + O 2 — » O 2 " + Ce 4+ , followed by reaction of the O 2 " anion with CO (NO) to give CO 3 (NO 3 ) and subsequent decomposition to CO 2 (NO 2 ) and O " and finally regeneration of Ce 3+ .
  • This reaction cycle can occur on pure CeO 2 and the nature / energy barrier of the Ce 4+ ⁇ Ce 3+ redox cycle can be probed using TPR (Temperature Programmed Reduction) with reduction peaks for surface CeO 2 at 350-60O 0 C.
  • the present invention relates to a method of making a OIC/OS host material for treatment of exhaust gases comprising forming a solid solution of a substantially cubic fluorite Ce-ZrOx material as determined by conventional XRD, introducing a base metal element in said material by exchanging pre-existing hydroxyl sites in said Ce-ZrOx material, under high pH conditions, to thereby incorporate and stabilize said base metal element in high dispersion within said Ce-ZrOx material.
  • the Ce-ZrOx material of the invention is an OIC/OS material having about 0.5 to about 95 mole % zirconium, about 0.5 to about 90 mole % cerium, and optionally about 0.1 to about 20 mole % R, wherein R is selected from the group consisting of rare earth metal(s), alkaline earth metal(s), and combinations comprising at least one of the foregoing, based upon 100 mole % metal component in the material.
  • the Ce-ZrOx material is an OIC/OS material based upon 100 mole % of the material comprising up to about 95 mole % zirconium; up to about 90 mole % cerium; up to about 25 mole % of a stabiliser selected from the group defined in the standard Periodic Table as rare earths, and combinations thereof comprising at least one of the stabilisers.
  • the base i.e. non Precious Group metal element is prepared as an alkaline solution, for example as an ammoniacal solution (ammonium hydroxide based solution) with a high pH as for example 8.0 to 9.5.
  • the base metal can be a member selected from the group consisting of transition metals, alkali metals, and alkaline earth metals.
  • the base metal element can also be introduced as a base metal complex with an organic amine in such cases where stable ammoniacal base metal solutions cannot be prepared.
  • a platinum / precious group metal can be added to the OIC/OS material in the conventional way.
  • Benefits and features of the present invention include: a) Provision of an OS material with enhanced low temperature reactivity and excellent hydrothermal durability; b) No disruption of activity and ancillary catalytic functions of the ion- exchanged adatoms e.g. NOx trap/ SCR, etc; c) Improved performance due to the enhanced stability, higher dispersion and hence higher accessibility of the gaseous reactants to the redox active elements; d) Advantage of pre-formed OS materials with desirable structural and textural properties e.g.
  • OS materials used to date present limitations with regard to their total Oxygen Storage Capacity, that is to say the amount of available oxygen as measured by TPR is typically lower than that expected from consideration of the total Ce IV content of the OS material.
  • Many data available to date are consistent with as little as only ca. 50% of the total Ce IV available undergoing reduction. At this time it is uncertain whether this is due to a fundamental issue, or due to limitations with the current synthetic method(s) employed in the manufacture of the OS material leading to a mixed Ce FV / Ce EU valency or whether a combination of additional chemical, structural or textural limitations are responsible.
  • OS materials provide only limited, if any, additional synergies to the emission control system.
  • ideal material components provide additional integrated chemical mechanisms to further enhance emissions control, e.g. NOx scavenging and reduction to N 2 .
  • OS materials are key components in realising highly active and durable vehicular exhaust emissions systems
  • the pre-existing synthesis methods and materials present significant limitations to development of the next generation of exhaust catalyst that will be required to comply with newer and ever more stringent emission targets.
  • What is required is a new class of OS materials that are active at lower temperatures, especially the Cold Start portion of vehicular applications to promote catalytic function.
  • These OS materials should also display high hydrothermal durability and be tolerant to potential exhaust poisons in order to enable then- use in the wide range of demanding exhaust environments.
  • Figure 1 compares the normalised mass loss response from a newly synthesised OS material versus its subsequent H 2 uptake response from H 2 TPR. The data shows a correlation between a mass loss feature (peak at ca. 45O 0 C) on the onset of redox activity.
  • Figure 2 shows a CO TPR experiment performed using a mass spectrometer as the detector. During the temperature ramp the onset of production of CO 2 , from the oxidation of CO by the active oxygen of the OS, is seen to correlate with a peak of water evolution / desorption from the OS. The water evolution is ascribed to de-hydroxylation of 2 * Ce 3+ -OH defect sites with the subsequent generation of H 2 O and an oxygen vacancy within the OS lattice. The formation of these oxygen vacancies are required to enable oxygen ion transport from the bulk to the surface to enable the OS to be redox active.
  • Figure 3 shows the dramatic promotion of H 2 TPR characteristics of a CeZrLaPrO 2 OS (OSl) by the post-synthetic modification by basic ion exchange of 2% Silver (Ag). Without wishing to be bound by theory, it is argued that this benefit arises from the exchange of the proton of the Ce 3+ -OH by Ag, with a resultant promotion of the oxygen ion conductivity of the material. This is ascribed to the elimination of the de-hydroxylation (and subsequent generation of lattice vacancies) phenomenon illustrated in Fig 1 and 2 which appears to be a requirement for the activation of the bulk of the crystal lattice to become redox active. The extent of this promotion is comparable to that noted for impregnation of PGM e.g. Pt, but at a fraction of the cost.
  • Figure 4 compares the H 2 TPR performance of a second CeZrLaPrO 2 mixed oxide (OS2) before and after post-synthetic basic exchange of l%Cu.
  • OS2 CeZrLaPrO 2 mixed oxide
  • Cu Copper
  • Figure 5 illustrates the impact of exchanged Cu loading on the redox performance of the OS2 versus the activity with a 2.21% CuO - SiO 2 reference powder.
  • the dramatic enhancement of redox activity is observed with increasing levels of Cu resulting in an increase of the large redox feature centred at 225-250 0 C.
  • This higher temperature peak is ascribed to CuO ensembles with a redox character more similar to bulk CuO, as can be seen by comparison with the CuO-SiO 2 .
  • the data again confirms a synergistic coupling of the redox chemistries of the OS and the dopant ion.
  • Figure 6 demonstrates the impact of low, but increasing, levels of Cobalt (Co) ion exchange on the redox performance of OS2. Benefits / decreased redox temperature are seen for Co levels as low as 0.02% by mass and the promotion continues at 0.1 and 1% with the latter showing a decrease of ca. 150°C in the temperature for peak redox.
  • Co Cobalt
  • Figure 7a confirms that the enhancement of redox properties may also be achieved using Iron (Fe).
  • Fe Iron
  • the performance of a CeZrLaYO 2 (OS3) undergoes dramatic promotion by the incorporation of Fe at either 2.5 or 5%.
  • comparison of the 2.5% exchanged Fe-OS3 versus an analogous composition, prepared by a commercial supplier in a manner similar to that described in US 6,585,944 Bl shows the comparable performance for the exchanged OS3 ( Figure 7b).
  • the exchanged sample prepared by a significantly simpler method, shows a small improvement in redox characteristic with a Ce reduction maximum ca. 40 °C lower than that for sample prepared by the deliberate synthesis method.
  • Figure 8 reflects the hydrothermal durability of the 2.5%Cu-exchanged OS2 material. This sample was subjected to two aging cycles, the first at 800 0 C / 10% steam / Air for 6h (an aging condition relevant to Diesel aftertreatment applications) and the second at 1100 0 C / dry air for 6h (to mimic a gasoline aging). After both aging cycles the low temperature redox feature is retained, even after the very severe HOO 0 C aging. This is consistent with a strong interaction between the exchanged cation and the OS lattice.
  • Figure 9 summarises a detailed X-ray Diffraction (XRD) characterisation study of Cu-exchanged OS2 as both a function of Cu loading and as a function of aging cycle.
  • the data confirms that for the 1 and 2.5% Cu exchange there is no discrete CuO formed, consistent with the proposed high dispersion. Only at 5%Cu is the presence of CuO recorded, consistent with an 'over-exchange' of the OS.
  • the XRD data corroborate the hydrothermal durability suggested by the TPR data in Fig. 8, with only significant changes in structure seen for aging at 800°C / 10% steam / Air / 6h. It is only after the severe 1100 0 C aging that structural changes are evident, but these changes are more consistent with phase disproportionation of the 'parent' OS and again for the 1 and 2.5% Cu samples there is no evidence for XRD discrete Cu-containing phases.
  • Figure 10 shows the impact of a typical 'Diesel' aging cycle (800 0 C/ 10% steam / Air for 6h) on the redox activity of 2.5%Fe-OS3. Again the material retains high redox function after aging, indeed after aging the peak redox temperature is now seen at lower temperatures (325 0 C vs 425 0 C fresh) and the redox feature associated with bulk Fe 2 O 3 is markedly attenuated suggesting an increased interaction and re-dispersion of the cations during the aging cycle.
  • FIG. 11 summarises a detailed X-ray Diffraction (XRD) characterisation study of Fe-exchanged OS3 as both a function of Fe loading and as a function of aging cycle.
  • Triethanolamine (TEA) was employed to generate the basic / alkaline precursor complex.
  • the data suggests that no discrete metal oxide (Fe 2 O 3 ) is formed within the range examined, again consistent with the proposed high dispersion.
  • Similar results are recorded after the aging at 800 0 C in air and steam, although significant sintering of the cubic phase crystals are recorded. Again it is only after the severe 110O 0 C aging that gross structural changes are evident. Firstly gross sintering of the cubic phase is evident with crystal diameters > 1000 A.
  • FIGS 12 and 13 illustrate a comparison between 2Ag-OSl compositions arrived by either exchange route or by a standard precipitation synthesis route.
  • These data reflect one of the strengths of the exchange method for OS promotion, i.e. the flexibility of the method to arrive at active and phase pure compositions normally difficult to achieve by direct synthesis.
  • the 2Ag-OSl sample produced by exchange demonstrates both phase purity and excellent low temperature redox, the same is not true for the sample produced by direct synthesis.
  • the latter material exhibits ca. 50% of the redox activity for the fresh sample, and with a shift of about 50 °C+ in temperature for the redox peaks.
  • the present invention relates to a modified host for an emission treatment catalyst and method for making the same.
  • the host is a substantially phase pure cubic fluorite (as determined by XRD method) of the Ce-ZrOx type which is well known in the art.
  • the modification is proposed to arise, whilst not wishing to be bound by theory, from an ion exchange of the Ce 3+ -OH hydroxyls, present in both the surface and to a lesser extent in the bulk of the crystal, by the base metal element / ion selected for this purpose.
  • the modified host materials may be applied advantageously to a wide range of emission control catalysts serving both gasoline (stoichiometric) and diesel (or other fuel lean) applications.
  • One particular example described herein is for the application of these materials is in the area of catalytic oxidation / regeneration of diesel particulate matter captured and 'stored' on a conventional wall flow filter.
  • This new generation of modified OS materials has been demonstrated as having particular benefit in affecting either lower temperature regeneration / oxidation of soot or an increased regeneration efficiency at a 'conventional' temperature as compared to non-modified OS materials.
  • This example is not exclusive, merely illustrative of the potential benefits that may be realised by employing active materials produced by this novel post-synthetic modification method.
  • the basic exchange for enhanced redox process describes a method for the modification of conventional cerium-zirconium-based mixed oxides, also known as, oxygen storage materials (OSM).
  • OSM oxygen storage materials
  • the process involves the treatment of the OSM with a basic, where possible preferentially ammoniacal metal solution.
  • Base metals i.e. common metals, currently being employed in this process include, but are not limited to, transition metals, e.g. silver, copper and cobalt, alkali metals e.g. potassium, alkaline earth metals e.g .calcium, strontium, barium.
  • transition metal as used herein means the 38 elements in groups 3 through 12 of the Periodic Table of the Elements.
  • the variables in the process include (1) the OSM / mixed oxide selected, (2) the metal used, and (3) the concentration of that metal.
  • Metal concentrations successfully employed have ranged from 0.02 to 5.0 weight-percent. However, at higher metal exchange levels bulk metal oxides may be formed which do not retain the synergistic coupling with the OSM. Hence, the most preferred range for ion exchange is 0.1 to 2.5 weight-percent.
  • the base metals are typically received as a metal salt or solution of salt e.g. nitrate. As indicated, most base metals form a water-soluble complex with ammonium hydroxide. In those instances wherein the ammoniacal complex is unstable an organic amine e.g. tri-ethanolamine may be employed instead.
  • the solution of an acidic metal solution is converted to a chemically basic form by addition of the ammoniacal base. The chemistry and amounts of base used vary with the metal used.
  • the resulting solution is then used to impregnate the mixed oxide powder, thereby ion-exchanging the surface and sub-surface Ce- OH hydroxyls (surface terminations and bulk defects which act as acidic centres under the conditions of synthesis).
  • the mixed oxide / OSM material of this invention comprises any known or predicted Cerium-containing or Ce-Zr-based stable solid solution.
  • the solid solution contains a cationic lattice with a single-phase, as determined by standard X-ray Diffraction method. More preferably this single-phase is a cubic structure, with a cubic fluorite structure being most preferred.
  • the ion exchange process may be performed without formation of additional bulk phase, as determined by XRD, providing the concentration of exchanged cation does not exceed the Ce-OH 'concentration' of the cubic fluorite lattice.
  • the OS material may include those OS materials disclosed in U.S. Pat.
  • the OS materials modified by the basic exchange method comprise a composition having a balance of sufficient amount of zirconium to decrease the reduction energies of Ce 4+ and the activation energy for mobility of 'O' within the lattice and a sufficient amount of cerium to provide the desired oxygen storage capacity.
  • the OS shall contain a sufficient amount of stabiliser e.g. yttrium, rare earth (La/Pr etc.) or combination thereof to stabilise the solid solution in the preferred cubic crystalline phase.
  • the OS materials modified by the basic exchange method should preferably be characterised by a substantially cubic fluorite structure, as determined by conventional XRD methods.
  • the percentage of the OS material having the cubic structure, both prior and post exchange, is preferably greater than about 95%, with greater than about 99% typical, and essentially 100% cubic structure generally obtained (i.e. an immeasurable amount of tetragonal phase based upon current measurement technology).
  • the exchanged OS material is further characterised in that it possesses large improvements in durable redox activity with respect to facile oxygen storage and increased release capacity e.g as determined by conventional Temperature Programmed Reduction (TPR) method.
  • TPR Temperature Programmed Reduction
  • the reduction of Ce+Cu is observed to occur at a temperature of about 300 to about 35O 0 C lower than would occur in the absence of the Cu dopant ( Figure 4).
  • the Ce+Fe reduction is shifted to lower temperatures by about 100 to about 200°C.
  • the OS material based upon 100 mole% of the material preferably comprises up to about 95 mole % zirconium; up to about 95 mole % cerium; up to about 20 mole % of a stabiliser or stabilisers selected from the group consisting yttrium, rare earths and combinations comprising at least one of the stabilisers.
  • the OS material prior to exchange is a solid solution of Ce-Zr-R-Nb, wherein "R” is a rare earth metal or a combination comprising at least one of the following metals yttrium, lanthanum, praseodymium, neodymium and combinations comprising at least one of these metals preferred.
  • R is a rare earth metal or a combination comprising at least one of the following metals yttrium, lanthanum, praseodymium, neodymium and combinations comprising at least one of these metals preferred.

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Abstract

La présente invention concerne un matériau conducteur d'ion oxygène (OIC)/de stockage d'oxygène (OS), plus particulièrement un OIC/OS présentant une structure cristalline cubique stable, associé à une méthode permettant d'activer les propriétés catalytiques du OIC/OS grâce à l'introduction post-synthèse de métaux non précieux, par le biais d'un processus d'échange basique (alcalin). L'invention concerne également l'application desdits matériaux pour contrôler des émissions de gaz d'échappement de véhicules.
PCT/EP2009/002262 2008-03-27 2009-03-27 Échange basique pour des matériaux de stockage d'oxygène (os) redox évolués destinés à des applications de contrôle des émissions WO2009118189A1 (fr)

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CN2009801108862A CN101980778A (zh) 2008-03-27 2009-03-27 用于排放控制应用的增强氧化还原os材料的碱性交换
JP2011501154A JP2011526197A (ja) 2008-03-27 2009-03-27 排出物質浄化用途のための強化されたレドックスｏｓ材料のための塩基性交換
EP09723698.8A EP2268394A1 (fr) 2008-03-27 2009-03-27 Échange basique pour des matériaux de stockage d'oxygène (os) redox évolués destinés à des applications de contrôle des émissions
BRPI0909381A BRPI0909381A2 (pt) 2008-03-27 2009-03-27 troca básica para intensificar os materiais "os" da redox para emissão de aplicações controle

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US3987908P 2008-03-27 2008-03-27
US61/039,879 2008-03-27
US61/308,879 2008-03-27
US12/240,170 2008-09-29
US12/240,170 US20090246109A1 (en) 2008-03-27 2008-09-29 Solid solutions and methods of making the same
US12/363,329 2009-01-30
US12/363,310 US9403151B2 (en) 2009-01-30 2009-01-30 Basic exchange for enhanced redox OS materials for emission control applications
US12/363,329 US20100196217A1 (en) 2009-01-30 2009-01-30 Application of basic exchange os materials for lower temperature catalytic oxidation of particulates
US12/363,310 2009-01-30

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PCT/EP2009/002261 WO2009118188A1 (fr) 2008-03-27 2009-03-27 Solutions solides et procédés de fabrication correspondant
PCT/EP2009/002263 WO2009118190A2 (fr) 2008-03-27 2009-03-27 Application de matériaux de stockage d'oxygène (os) d'échange basique pour une oxydation catalytique de matières particulaires à basse température
PCT/EP2009/002262 WO2009118189A1 (fr) 2008-03-27 2009-03-27 Échange basique pour des matériaux de stockage d'oxygène (os) redox évolués destinés à des applications de contrôle des émissions

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PCT/EP2009/002261 WO2009118188A1 (fr) 2008-03-27 2009-03-27 Solutions solides et procédés de fabrication correspondant
PCT/EP2009/002263 WO2009118190A2 (fr) 2008-03-27 2009-03-27 Application de matériaux de stockage d'oxygène (os) d'échange basique pour une oxydation catalytique de matières particulaires à basse température

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JP2011526198A (ja) 2011-10-06
BRPI0909381A2 (pt) 2016-05-17
EP2259870A2 (fr) 2010-12-15
KR20100135858A (ko) 2010-12-27
CN102006923A (zh) 2011-04-06
WO2009118190A4 (fr) 2010-03-18
WO2010002486A3 (fr) 2010-03-25
WO2009118188A1 (fr) 2009-10-01
JP2011515221A (ja) 2011-05-19
CN101980778A (zh) 2011-02-23
WO2009118190A2 (fr) 2009-10-01
WO2009118190A3 (fr) 2010-01-21
CN102006923B (zh) 2014-08-27
BRPI0909377A2 (pt) 2017-06-13
JP2011526197A (ja) 2011-10-06
BRPI0909386A2 (pt) 2015-10-06
WO2010002486A2 (fr) 2010-01-07
WO2009118189A4 (fr) 2009-11-19
EP2268395A2 (fr) 2011-01-05
EP2259870A4 (fr) 2017-11-15
KR20160129913A (ko) 2016-11-09
CN102112223A (zh) 2011-06-29
KR20110008190A (ko) 2011-01-26

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