EP2403649B1 - Magnetische hydrophobe agglomerate - Google Patents

Magnetische hydrophobe agglomerate Download PDF

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Publication number
EP2403649B1
EP2403649B1 EP10706247.3A EP10706247A EP2403649B1 EP 2403649 B1 EP2403649 B1 EP 2403649B1 EP 10706247 A EP10706247 A EP 10706247A EP 2403649 B1 EP2403649 B1 EP 2403649B1
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EP
European Patent Office
Prior art keywords
particle
active substance
magnetic
particles
agglomerates
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Not-in-force
Application number
EP10706247.3A
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German (de)
English (en)
French (fr)
Other versions
EP2403649A1 (de
Inventor
Imme Domke
Hartmut Hibst
Alexej Michailovski
Norbert Mronga
Werner Hartmann
Wolfgang Krieglstein
Vladimir Danov
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BASF SE
Siemens AG
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BASF SE
Siemens AG
Siemens Corp
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Application filed by BASF SE, Siemens AG, Siemens Corp filed Critical BASF SE
Priority to PL10706247T priority Critical patent/PL2403649T3/pl
Priority to EP10706247.3A priority patent/EP2403649B1/de
Publication of EP2403649A1 publication Critical patent/EP2403649A1/de
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
    • B03C—MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
    • B03C1/00—Magnetic separation
    • B03C1/005—Pretreatment specially adapted for magnetic separation
    • B03C1/015—Pretreatment specially adapted for magnetic separation by chemical treatment imparting magnetic properties to the material to be separated, e.g. roasting, reduction, oxidation

Definitions

  • the present invention relates to an agglomerate of at least one particle P, which is hydrophobized on the surface with at least one first surfactant, and at least one magnetic particle MP, which is hydrophobized on the surface with at least one second surfactant, a process for producing these agglomerates and the use of the agglomerates to separate a particle P from mixtures containing these particles P and other components.
  • Agglomerates containing at least one magnetic particle and at least one further component are already known from the prior art.
  • US 4,643,822 A discloses a method for separating desired substances from mixtures of substances.
  • an agglomerate of at least one magnetic material and the desired material is produced by coordinated zeta potentials of the respective surfaces.
  • a mixture of metallic copper and lead granules is separated by reacting the amine-dispersed colloid with US 4,643,822 A is added.
  • the amine-dispersed colloid is prepared by mixing a magnetite suspension dissolved in hydrochloric acid with dodecylamine.
  • WO 2009/010422 A1 discloses a process for ore enrichment by means of hydrophobic solid surfaces.
  • a slurry or dispersion of the mixture to be treated is prepared, which is brought into contact with at least one solid hydrophobic surface for attachment of the at least one hydrophobic substance to be separated and the solid hydrophobic surface to which the at least one hydrophobic substance is attached. is removed from the dispersion or slurry.
  • Solid hydrophobic surface means according to WO 2009/010422 A1 For example, a plate or a treadmill, or the sum of the surfaces of many moving particles, for example, the individual surfaces of a plurality of balls.
  • US 4,657,666 discloses a method for enrichment of ores where the ginger ore is reacted with magnetic particles to form agglomerates due to the hydrophobic interactions.
  • the magnetic particles are hydrophobized by treatment with hydrophobic compounds on the surface, so that a connection to the value ore takes place.
  • the agglomerates are then separated from the mixture by a magnetic field.
  • the document also discloses that the ores are treated with a surface activating solution of 1% sodium ethylxanthogenate before the magnetic particle is added.
  • US 4,834,898 discloses a method of separating nonmagnetic materials by contacting them with magnetic reagents encased in two layers of surfactants. US 4,834,898 further discloses that the surface charge of the non-magnetic particles to be separated may be affected by various types and concentrations of electrolyte reagents. For example, the surface charge is altered by the addition of multivalent anions, for example tripolyphosphate ions.
  • WO 2007/008322 A1 discloses a magnetic particle hydrophobized on the surface for separating impurities from mineral substances by magnetic separation techniques.
  • a dispersing agent selected from sodium silicate, sodium polyacrylate or sodium hexametaphosphate may be added to the solution or dispersion.
  • the object of the present invention is to provide agglomerates of at least one magnetic particle and at least one further particle, wherein the at least one further particle is preferably a value component.
  • the agglomerates according to the invention should be distinguished by a high stability in water or polar media, but should not be stable in non-polar media. Furthermore, these agglomerates should have a hydrophobic character.
  • a further object of the present invention is to provide corresponding agglomerates which, due to their magneticity, can be separated by a magnetic field from further, non-magnetic and non-hydrophobic components.
  • hydrophobic means that the corresponding particle can be hydrophobized subsequently by treatment with the at least one surface-active substance. It is also possible that a per se hydrophobic particle is additionally hydrophobized by treatment with the at least one surface-active substance.
  • Hydrophobic in the context of the present invention means that the surface of a corresponding "hydrophobic substance” or a “hydrophobized substance” has a contact angle of> 90 ° with water against air.
  • Hydrophobic in the context of the present invention means that the surface of a corresponding “hydrophilic substance” has a contact angle of ⁇ 90 ° with water against air.
  • At least one particle P is present, which is hydrophobized on the surface with at least one first surface-active substance.
  • the at least one particle P contains at least one metal compound and / or carbon.
  • the at least one particle P contains a metal compound selected from the group of sulfidic ores, oxidic and / or carbonate-containing ores, for example azurite [Cu 3 (CO 3 ) 2 (OH) 2 ], or malachite [Cu 2 [. (OH) 2
  • the at least one particle P consists of said metal compounds.
  • sulfide ores which can be used according to the invention are selected, for example, from the group of copper ores consisting of covellite CuS, molybdenum (IV) sulfide, chalcopyrite (copper gravel) CuFeS 2 , bornite Cu 5 FeS 4 , chalcocite (copper luster) Cu 2 S, sulfides iron, lead, zinc or molybdenum, ie FeS / FeS 2 , PbS, ZnS or MoS 2 and mixtures thereof.
  • copper ores consisting of covellite CuS, molybdenum (IV) sulfide, chalcopyrite (copper gravel) CuFeS 2 , bornite Cu 5 FeS 4 , chalcocite (copper luster) Cu 2 S, sulfides iron, lead, zinc or molybdenum, ie FeS / FeS 2 , PbS, ZnS or MoS 2 and mixtures thereof.
  • Suitable oxidic compounds are those of metals and semimetals, for example silicates or borates or other salts of metals and semimetals, for example phosphates, sulfates or oxides / hydroxides / carbonates and further salts, for example azurite [Cu 3 (CO 3 ) 2 (OH ) 2 ], malachite [Cu 2 [(OH) 2 (CO 3 )]], barite (BaSO 4 ), monacite ((La-Lu) PO 4 ).
  • metals and semimetals for example silicates or borates or other salts of metals and semimetals, for example phosphates, sulfates or oxides / hydroxides / carbonates and further salts, for example azurite [Cu 3 (CO 3 ) 2 (OH ) 2 ], malachite [Cu 2 [(OH) 2 (CO 3 )]], barite (BaSO 4 ), monacite ((La-Lu) PO 4 ).
  • Suitable noble metals are, for example, Au, Pt, Pd, Rh, etc., where Pt is mainly alloyed.
  • Suitable Pt / Pd ores are Sperrlith PtAs 2 , Cooperit PtS or Braggit (Pt, Pd, Ni) S.
  • the at least one particle P present in the agglomerate according to the invention is hydrophobized on the surface with at least one first surface-active substance and the at least one magnetic particle MP is hydrophobicized with at least one second surface-active substance.
  • the at least one first and the at least one second surface-active substance are different.
  • the at least one first and the at least one second surface-active substance are identical.
  • surface-active substance means a substance which is capable of changing the surface of the particle P so that it becomes hydrophobic in the sense of the abovementioned definition.
  • A is a linear or branched C 4 -C 12 -alkyl, very particularly preferably a linear C 4 - or C 8 -alkyl.
  • optionally present heteroatoms according to the invention are selected from N, O, P, S and halogens such as F, Cl, Br and I.
  • A is preferably a linear or branched, preferably linear, C 6 -C 20 -alkyl.
  • A is preferably a branched C 6 -C 14 -alkyl, wherein the at least one substituent, preferably having 1 to 6 carbon atoms, preferably in the 2-position, is present, for example 2-ethylhexyl and / or 2-propylheptyl.
  • n 2 in the abovementioned formulas, then two identical or different, preferably identical, groups A are bound to a group Z.
  • Preferred counterions in these compounds are cations selected from the group consisting of hydrogen, NR 4 + where R is independently hydrogen and / or C 1 -C 8 -alkyl, alkali or alkaline-earth metals, in particular sodium or potassium.
  • Very particularly preferred compounds of general formula (I) are selected from the group consisting of sodium or potassium n-octylxanthate, sodium or potassium butylxanthate, sodium or potassium di-n-octyl dithiophosphinate, sodium or potassium di -n-octyl dithiophosphate, octanethiol and mixtures of these compounds.
  • particularly preferred surface-active substances are xanthates, thiocarbamates or hydroxamates.
  • Other suitable surface-active substances are, for example, in EP 1200408 B1 described.
  • metal oxides for example FeO (OH), Fe 3 O 4 , ZnO etc.
  • carbonates for example azurite [Cu (CO 3 ) 2 (OH) 2 ], malachite [Cu 2 [(OH) 2 CO 3 ]] particularly preferred surface-active substances octylphosphonic acid (OPS), (EtO) 3 Si-A, (MeO) 3 Si-A, having the abovementioned meanings for A.
  • particularly preferred surface-active substances are mono-, di- and trithiols or xanthates.
  • Z is - (X) n -CS 2 - , - (X) n -PO 2 - or - (X) n -S - where X is O and n is 0 or 1 and one Cation selected from hydrogen, sodium or potassium.
  • Very particularly preferred surface-active substances are 1-octanethiol, potassium n-octyl xanthate, potassium butylxanthate, octylphosphonic acid or a compound of the following formula (IV)
  • At least one particle P is present, which is hydrophobized with at least one surface-active substance.
  • P is Cu 2 S, which is hydrophobized with the potassium salts of ethyl, butyl octyl or other aliphatic or branched xanthates or mixtures thereof.
  • the particle P is a Pd-containing alloy, preferably with the Potassium salts of ethyl, butyl octyl or other aliphatic or branched xanthates or mixtures thereof is hydrophobized, most preferably, this particle is hydrophobicized with mixtures of these Kaliumxanthate and thiocarbamates.
  • agglomerates are preferred in which the particle contains P Rh, Pt, Pd, Au, Ag, Ir or Ru.
  • the surface-active hydrophobization is adapted to the corresponding mineral surface, so that it comes to an optimal interaction between surface-active substance and the particle P, which contains Rh, Pt, Pd, Au, Ag, Ir or Ru.
  • Methods for hydrophobizing the surface of the particles P which can be used in the agglomerates according to the invention are known to the person skilled in the art, for example by contacting the particles P with the at least one first surface-active substance, for example in bulk or in dispersion.
  • the particles P and the at least one surfactant are added and mixed together without additional dispersant in the appropriate amounts.
  • Suitable mixing apparatuses are known to the person skilled in the art, for example mills, such as ball mill (planetary vibrating mills).
  • the components are combined in a dispersion, preferably in suspension.
  • Suitable dispersants are, for example, water, water-soluble organic compounds, for example alcohols having 1 to 4 carbon atoms, and mixtures thereof.
  • the at least one first surface-active substance is generally present on the at least one particle P in an amount of 0.01 to 5% by weight, preferably 0.01 to 0.1% by weight, based on the sum of at least a first surfactant and at least one particle P.
  • the optimum content of surfactant generally depends on the size of the particles P.
  • the particles P may generally be regularly shaped, for example spherical, cylindrical, cuboidal, or irregular, for example splintered.
  • Particle P 2 may be selected from the group referred to particle P.
  • Particle P 2 may also be selected from the group of oxidic metal or semimetal compounds, for example SiO 2 .
  • the at least one particle P which is hydrophobized on the surface with at least one first surface-active substance, generally has a diameter of 1 nm to 10 mm, preferably 10 to 100 ⁇ m. In asymmetrically shaped Particles are considered the diameter of the longest distance in the particle.
  • the agglomerate according to the invention further comprises at least one magnetic particle MP, which is hydrophobized on the surface with at least one second surface-active substance.
  • the magnetic particles MP can generally be regularly shaped, for example, spherical, cylindrical, cuboidal, or irregular, for example splinter-shaped.
  • the at least one magnetic article MP which is hydrophobized on the surface with at least one second surface-active substance, generally has a diameter of 10 nm to 1000 mm, preferably 100 nm to 1 mm, particularly preferably 500 nm to 500 ⁇ m, very particularly preferably 1 up to 100 ⁇ m, on.
  • the diameter considered to be the longest distance in the particle.
  • magnétique particles MP which have a similar particle size distribution as the particles P. These size distributions may be mono-, bi- or trimodal.
  • the magnetic particles MP may, if appropriate, be converted into the appropriate size prior to the use according to the invention using methods known to those skilled in the art, for example by grinding.
  • the magnetic particles MP which can be used according to the invention preferably have a BET specific surface area of from 0.01 to 50 m 2 / g, particularly preferably from 0.1 to 20 m 2 / g, very particularly preferably from 0.2 to 10 m 2 / g.
  • the magnetic particles MP which can be used according to the invention preferably have a density (measured to DIN 53193) of 3 to 10 g / cm 3 , particularly preferably 4 to 8 g / cm 3 .
  • B is a linear or branched C 6 -C 18 -alkyl, preferably linear C 8 -C 12 -alkyl, very particularly preferably a linear C 12 -alkyl.
  • optionally present heteroatoms according to the invention are selected from N, O, P, S and halogens such as F, Cl, Br and I.
  • Y is selected from the group consisting of - (X) n -SiHal 3 , - (X) n -SiHHal 2 , - (X) n -SiH 2 Hal where Hal is equal to F, Cl, Br, I, and anionic groups such as - (X) n -SiO 3 3- , - (X) n -CO 2 - , - (X) n -PO 3 2- , - (X) n -PO 2 S 2 - , - (X) n -POS 2 2- , - (X) n -PPS 3 2- , - (X) n -PPS 2 - , - (X) n -POS - , - (X) n -PO 2 - , - (X) n -CO 2 - , - (X) n -CS 2 - , - (X) n -CO 2 -
  • n 2 in the abovementioned formulas, then two identical or different, preferably identical, groups B are bound to a group Y.
  • Very particularly preferred hydrophobizing substances of the general formula (III) are alkyltrichlorosilanes (alkyl group having 6-12 carbon atoms), alkyltrimethoxysilanes (alkyl group having 6-12 carbon atoms), octylphosphonic acid, lauric acid, oleic acid, stearic acid or mixtures thereof.
  • the at least one second surface-active substance is present on the at least one magnetic particle MP, preferably in an amount of from 0.01 to 0.1% by weight, based on the sum of at least one second surface-active substance and at least one magnetic particle MP.
  • the optimum amount of at least one second surface-active substance is dependent on the size of the magnetic particle MP.
  • At least one magnetic particle MP which is hydrophobicized with at least one second surface-active substance, magnetite, hydrophobed with dodecyltrichlorosilane and / or magnetite, hydrophobicized with octylphosphonic acid.
  • the magnetic particles MP rendered hydrophobic with at least one second surface-active substance can be prepared by all processes known to those skilled in the art, preferably as described with regard to the hydrophobized particles P.
  • the at least one particle P which is hydrophobized on the surface with at least one first surface-active substance
  • the at least one magnetic particle MP which is hydrophobized on the surface with at least one second surface-active substance
  • the at least one particle P is present on the surface with at least one first surface active substance Substance is hydrophobicized, at 10 to 90 wt .-%, preferably 20 to 80 wt .-%, particularly preferably 40 to 60 wt .-%, and the at least one magnetic particle MP, which hydrophobicized at the surface with at least one second surfactant is, to 10 to 90 wt .-%, preferably 20 to 80 wt .-%, particularly preferably 40 to 60 wt .-%, before, in each case based on the total agglomerate, the sum in each case 100 wt .-% results.
  • the agglomerate according to the invention at least one particle P, which is hydrophobized on the surface with at least one first surface-active substance, and 50% by weight at least one magnetic particle MP, which at least with the surface a second surfactant is hydrophobized before. It must be ensured that, depending on the magnetic properties of the magnetic particles MP, the agglomerate as a whole can still be deflected magnetically under the influence of an external magnetic field.
  • the ratio P to MP is particularly preferred if an external magnetic field (which can be generated, for example, by a strong CoSm permanent magnet) can still magnetically deflect these particles if the agglomerates move with a flow of 300 mm / sec. at a 90 ° angle to the external magnet. Further, it is most preferred that the hydrophobic interactions between P and MP are strong enough that they are not torn apart at this flow rate.
  • the bond between the at least one particle P, which is hydrophobized on the surface with at least one first surface-active substance, and the at least one magnetic particle, which is hydrophobized on the surface with at least one second surface-active substance, takes place in the agglomerate according to the invention by hydrophobic interactions.
  • the diameter of the agglomerates according to the invention is dependent on the percentage of the particles P and the magnetic particles MP, the diameters of the particles P and magnetic particles MP, as well as the spaces between the particles, which are dependent on the type and amount of surface-active substances.
  • the agglomerates according to the invention generally have a magneticity, so that an external magnetic field, which can be generated, for example, by a strong CoSm permanent magnet, can at least still magnetically deflect these agglomerates if the agglomerates move with a flow of 300 mm / sec. at a 90 ° angle to the external magnet.
  • the hydrophobic interactions between P and MP within the agglomerates are generally strong enough that they remain stable at said flow rate, ie, are not torn apart.
  • the agglomerates according to the invention can be cleaved in a non-polar medium, for example diesel or acetone, preferably without the at least one particle P or the at least one magnetic particle MP being destroyed.
  • a non-polar medium for example diesel or acetone
  • the agglomerates according to the invention can be prepared, for example, by contacting the particles P which have been rendered hydrophobic with the at least one first surface-active substance, and the hydrophobicized with the at least one second surface-active substance MP, for example, in bulk or in dispersion.
  • the hydrophobized particles P and the hydrophobized magnetic particles MP are added and mixed together without additional dispersant in the appropriate amounts.
  • the particles P and the magnetic particles MP are added and mixed together in the corresponding amounts in the presence of the at least one first and at least one second surface-active substance without further dispersing agent.
  • Suitable mixing apparatuses are known to the person skilled in the art, for example mills, such as ball mill.
  • Dispersants suitable for the process according to the invention are, for example, water, water-soluble organic compounds, for example alcohols having 1 to 4 carbon atoms, and mixtures thereof.
  • the present invention also relates to a method for producing agglomerates according to the invention comprising contacting the particles P hydrophobized with the at least one first surfactant, and the magnet article MP hydrophobized with the at least one second surfactant, to obtain the agglomerates.
  • the process according to the invention is generally carried out at a temperature of 5 to 50 ° C., preferably at ambient temperature.
  • the process according to the invention is generally carried out at atmospheric pressure.
  • agglomerates After obtaining the agglomerates according to the invention, these can be separated from an optionally present solvent or dispersion medium by methods known to the person skilled in the art, for example by filtration, decanting, sedimentation and / or magnetic processes.
  • the agglomerates according to the invention can be used to separate corresponding particles P from mixtures containing these particles P and further components.
  • particle P may be an ore and the other components may be gait.
  • the agglomerates can be cleaved after separation by methods known to those skilled in the art.
  • the present invention also relates to the use of the agglomerates according to the invention for the separation of a particle P from mixtures containing these particles P and other components, for example for the separation of ores from raw ores containing the gangue.
  • the system is poured into water.
  • the hydrophobic agglomerates according to the invention are formed between the hydrophobic magnetite and the selectively hydrophobized copper sulfide. These agglomerates can by the action of a strong permanent magnet at flow rates greater than 320 mm / sec. are held perpendicular to the magnet without the hydrophobic agglomerates are destroyed.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Manufacture And Refinement Of Metals (AREA)
  • Soft Magnetic Materials (AREA)
  • Powder Metallurgy (AREA)
  • Hard Magnetic Materials (AREA)
  • Compounds Of Iron (AREA)
  • Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)
  • Separation Of Suspended Particles By Flocculating Agents (AREA)
  • Glanulating (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Extraction Or Liquid Replacement (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
EP10706247.3A 2009-03-04 2010-03-03 Magnetische hydrophobe agglomerate Not-in-force EP2403649B1 (de)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PL10706247T PL2403649T3 (pl) 2009-03-04 2010-03-03 Magnetyczne aglomeraty hydrofobowe
EP10706247.3A EP2403649B1 (de) 2009-03-04 2010-03-03 Magnetische hydrophobe agglomerate

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP09154285 2009-03-04
PCT/EP2010/052667 WO2010100180A1 (de) 2009-03-04 2010-03-03 Magnetische hydrophobe agglomerate
EP10706247.3A EP2403649B1 (de) 2009-03-04 2010-03-03 Magnetische hydrophobe agglomerate

Publications (2)

Publication Number Publication Date
EP2403649A1 EP2403649A1 (de) 2012-01-11
EP2403649B1 true EP2403649B1 (de) 2013-08-28

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EP10706247.3A Not-in-force EP2403649B1 (de) 2009-03-04 2010-03-03 Magnetische hydrophobe agglomerate

Country Status (17)

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US (1) US8377313B2 (enExample)
EP (1) EP2403649B1 (enExample)
JP (1) JP5683498B2 (enExample)
CN (1) CN102341179B (enExample)
AR (1) AR076077A1 (enExample)
AU (1) AU2010220284B2 (enExample)
BR (1) BRPI1011516A8 (enExample)
CA (1) CA2752881C (enExample)
EA (1) EA020958B1 (enExample)
ES (1) ES2435631T3 (enExample)
MX (1) MX2011009082A (enExample)
PE (1) PE20120731A1 (enExample)
PL (1) PL2403649T3 (enExample)
PT (1) PT2403649E (enExample)
UA (1) UA103077C2 (enExample)
WO (1) WO2010100180A1 (enExample)
ZA (1) ZA201107236B (enExample)

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PE20170804A1 (es) 2014-11-27 2017-07-04 Basf Se Mejora de la calidad del concentrado
CA2966807C (en) 2014-11-27 2023-05-02 Basf Se Energy input during agglomeration for magnetic separation
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CN106076602A (zh) * 2016-06-29 2016-11-09 昆明理工大学 一种磁介质团聚弱磁选富集氧化锌矿的方法
WO2018006959A1 (de) * 2016-07-06 2018-01-11 Friedrich-Alexander-Universität Erlangen-Nürnberg Kern-hülle-partikel
AU2018309321A1 (en) * 2017-08-03 2020-02-27 Basf Se Separation of a mixture using magnetic carrier particles
HUE061858T2 (hu) * 2017-09-29 2023-08-28 Basf Se Grafitrészecskék koncentrálása hidrofób mágneses részecskékkel történõ agglomerációval
JP7152003B2 (ja) * 2018-08-22 2022-10-12 河合石灰工業株式会社 高熱伝導性無機フィラー複合粒子及びその製造方法
CN109078761B (zh) * 2018-09-27 2020-11-27 江西理工大学 一种利用磁性疏水颗粒强化难处理硫化镍矿浮选的方法
CN109078760B (zh) * 2018-09-27 2020-07-31 江西理工大学 用带磁性疏水颗粒提高微细粒硫化铜矿浮选回收率的方法
CN110216020B (zh) * 2019-04-23 2020-11-03 中南大学 一种荷电磁性疏水材料及其制备方法和应用

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US20110309003A1 (en) 2011-12-22
PT2403649E (pt) 2013-11-07
JP5683498B2 (ja) 2015-03-11
CA2752881C (en) 2017-07-04
WO2010100180A1 (de) 2010-09-10
CN102341179A (zh) 2012-02-01
AR076077A1 (es) 2011-05-18
ES2435631T3 (es) 2013-12-20
AU2010220284A1 (en) 2011-09-08
PL2403649T3 (pl) 2014-01-31
CN102341179B (zh) 2014-08-13
AU2010220284B2 (en) 2016-02-18
MX2011009082A (es) 2011-09-27
JP2012519073A (ja) 2012-08-23
PE20120731A1 (es) 2012-06-15
BRPI1011516A2 (pt) 2016-03-29
EA201190196A1 (ru) 2012-06-29
EA020958B1 (ru) 2015-03-31
EP2403649A1 (de) 2012-01-11
CA2752881A1 (en) 2010-09-10
US8377313B2 (en) 2013-02-19
UA103077C2 (uk) 2013-09-10
ZA201107236B (en) 2012-12-27
BRPI1011516A8 (pt) 2017-10-03

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