EP2142283A2 - Process for enriching a gaseous effluent with acid gases - Google Patents
Process for enriching a gaseous effluent with acid gasesInfo
- Publication number
- EP2142283A2 EP2142283A2 EP08787896A EP08787896A EP2142283A2 EP 2142283 A2 EP2142283 A2 EP 2142283A2 EP 08787896 A EP08787896 A EP 08787896A EP 08787896 A EP08787896 A EP 08787896A EP 2142283 A2 EP2142283 A2 EP 2142283A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- derivatives
- gas
- hydrates
- compounds
- amphiphilic compound
- 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.)
- Withdrawn
Links
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1493—Selection of liquid materials for use as absorbents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1456—Removing acid components
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2257/00—Components to be removed
- B01D2257/50—Carbon oxides
- B01D2257/504—Carbon dioxide
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02C—CAPTURE, STORAGE, SEQUESTRATION OR DISPOSAL OF GREENHOUSE GASES [GHG]
- Y02C20/00—Capture or disposal of greenhouse gases
- Y02C20/20—Capture or disposal of greenhouse gases of methane
Definitions
- the present invention relates to the field of the separation of acidic compounds such as hydrogen sulfide (H 2 S) or carbon dioxide (CO 2 ) contained in a gas flow, for example hydrocarbon natural gas, fumes, or other industrial effluent.
- acidic compounds such as hydrogen sulfide (H 2 S) or carbon dioxide (CO 2 ) contained in a gas flow, for example hydrocarbon natural gas, fumes, or other industrial effluent.
- the present invention proposes to use the formation of gas hydrates in order to remove the most acidic compounds from the gas stream to enrich in acidic compounds another gaseous effluent while having the possibility of increasing the delivery pressure.
- a process for the deacidification of a gas which comprises a step of extracting the acidic compounds contained in the gas to be treated by contacting this gas with the regenerated solvent in an absorber operating at the pressure of the gas to be treated, is followed.
- a thermal regeneration step of the solvent generally operating at a pressure slightly above atmospheric pressure. This thermal regeneration is generally carried out in a column equipped with a bottom reboiler and an overhead condenser for cooling the acidic compounds released by the regeneration and to recycle the condensates at the top of the regenerator as reflux.
- Document US-7128777 discloses a process for separating hydrate formation from acid gases contained in a gas stream. This patent uses water both as a hydrate component and as a transport medium from the hydrate phase to a separator and then to compressors. The dual function of water as a component and transport medium is likely to limit the conversion of water into hydrate and lead to the formation of hydrate blocks that may clog pipes.
- the present invention proposes to use a water-immiscible phase as a water dispersion medium and a hydrate phase transport medium, making it possible at the same time to avoid the risks of clogging during the transport of the hydrate slurry. to improve the transfer of the acidic gas to an aqueous phase, and to increase the rate of conversion of water into hydrates.
- one or more amphiphilic additives optionally having the property of lowering the hydrate formation temperature and / or modifying the formation and agglomeration mechanisms are used.
- the present invention relates to a process for enriching acid compounds with a gaseous effluent that comprises the following steps:
- a charge gas and a mixture of at least two liquid phases which are immiscible with one another, including an aqueous phase, said feed gas containing at least acid compounds, are introduced into a contactor;
- said hydrates are transported in dispersion in the immiscible phase in the aqueous phase by pumping to a hydrate dissociation tank,
- the conditions for dissociation of the hydrates are established in the said flask; the gas resulting from the dissociation is discharged, the said gas being enriched in acidic compounds with respect to the charge gas,
- the pressure of the hydrate dispersion can be increased by a factor between 2 and 200 times the pressure of the feed gas.
- the amphiphilic compound may comprise a hydrophilic part and a part having a high affinity with the phase immiscible with the aqueous phase.
- FIG. 1 shows schematically the method according to the invention
- FIG. 2 shows the test device.
- the acid gas enrichment process of a gaseous effluent using gas hydrates as an enriching agent comprises three main steps illustrated with the aid of FIG.
- a first treatment step for contacting the feed gas containing acidic compounds with a mixture of at least two immiscible liquid phases, at least one of which consists of water, and preferably of amphiphilic molecules .
- the gas and the liquid phases are brought into contact under conditions of pressure and temperature compatible with the formation of a hydrate phase consisting of acidic compounds and water. This formation can be aided by the addition of one or more suitable additives.
- This first step allows the sequestration of a large proportion of acid gas in the hydrate phase.
- the gas hydrate particles thus enriched in acidic compounds are dispersed in the water immiscible liquid and transported in the form of a suspension of solids. The non-hydrated gas is thus depleted of acidic compounds.
- the formation of hydrate is done in the contactor R1 in which the charge gas enters via the pipe 2, after compression of the inlet gas through the pipe 1 with the aid of the compressor K1.
- the conduit 7 supplies the fluid mixture contactor with two immiscible liquid phases, one of which is water, and preferably with at least one amphiphilic compound.
- the depleted gas is discharged through line 9, while the hydrate slurry exits the bottom of the contactor via line 3.
- the gas stream thus obtained has a content and a partial pressure of acid gas from two to one hundred times greater than that of the feed gas.
- the pump P1 pressurises the slurry through line 4 into the dissociation tank R2.
- the gas enriched in acidic compounds is evacuated via line 5, and optionally compressed by compressor K2 to be injected, for example into an underground reservoir via line 8.
- step (3) the mixture of liquids resulting from step (2), and comprising predominantly the two immiscible liquids, the amphiphilic compound (s), and / or possibly other additives which can help to formation of a suspension of hydrates in the form of dispersed particles, is expanded / cooled to be returned by the conduits 6 and 7 in the contactor Rl of step 1.
- At least one amphiphilic compound which has the property of lowering the formation temperature of the hydrates and / or modify the mechanisms of formation and agglomeration. These modifications can be used particularly for the transport of the hydrate dispersion.
- the proportions of the water / solvent mixture may be between 0.5 / 99.5% and 60% by volume, and preferably between 10/90 and 50/50%, and more particularly between 20/80 and 40% by weight. 60% in volume.
- amphiphilic compounds are chemical compounds (monomer or polymer) having at least one hydrophilic or polar chemical group, having a high affinity with the aqueous phase and at least one chemical group having high affinity with the solvent
- hydrophobic (commonly referred to as hydrophobic).
- non-aggregated hydrate particles are obtained in the solvent.
- the hydrate block formation is thus avoided and the dispersion of the hydrate particles remains pumpable, the use of a water-immiscible solvent optionally makes it possible to limit the residual water content of the enriched acid compounds released during dissociation of hydrates.
- the amphiphilic compound may be added to said mixture in a proportion of between 0.1 and 10% by weight, and preferably between 0.1 and 5% by weight, relative to the immiscible phase in the aqueous phase. i.e. the solvent.
- the solvent used for the process can be chosen from several families: hydrocarbon solvents, silicone type solvents, halogenated or perhalogenated solvents. In the case of hydrocarbon solvents.
- the solvent may be selected from
- aliphatic cuts for example isoparaffinic sections having a flash point sufficiently high to be compatible with the process according to the invention
- organic solvents such as aromatic cuts or naphthenic cuts may also be used with the same flash point conditions,
- the hydrocarbon solvent for the process is characterized in that its flash point is greater than 40 ° C., and preferably greater than 75 ° C. and more precisely greater than 100 ° C. Its crystallization point is less than -5 ° C.
- Solvents of silicone type are chosen for example from:
- PDMS linear polydimethylsiloxane
- the unit D represents the dimethylsiloxane monomer unit, poly (trifluoropropyl methyl siloxane).
- the halogenated or perhalogenated solvents for the process are chosen from perfluorocarbons (PFCs), hydrofluoroethers (HFE) and perfluoropolyethers (PFPE).
- PFCs perfluorocarbons
- HFE hydrofluoroethers
- PFPE perfluoropolyethers
- the halogenated or perhalogenated solvent for the process is characterized in that its boiling point is greater than or equal to 70 ° C. under pressure atmospheric and that its viscosity is less than 1 Pa. s at ambient temperature and at atmospheric pressure.
- amphiphilic compounds include a hydrophilic moiety which can be either neutral, anionic, cationic, or even zwitterionic.
- the part having a high affinity with the solvent (designated as hydrophobic) can be either hydrocarbon-based, or silicone or fluoro-silicone, or still halogenated or perhalogenated.
- hydrocarbon amphiphilic compounds used alone, or in mixtures, to facilitate the formation and / or transport of the hydrates according to the present invention are chosen from nonionic, anionic, cationic or zwitterionic amphiphilic compounds.
- the nonionic compounds are characterized in that they contain: a hydrophilic part comprising either alkylene oxide groups, hydroxyl groups or even amino alkylene groups,
- hydrophobic part comprising a hydrocarbon chain derived from an alcohol, a fatty acid, an alkylated derivative of a phenol or a polyolefin, for example derived from isobutene or butene.
- the bond between the hydrophilic part and the hydrophobic part may, for example be an ether, ester or amide function. This bond can also be obtained by a nitrogen or sulfur atom.
- nonionic amphiphilic hydrocarbon compounds mention may be made of oxyethylated fatty alcohols, alkylphenol alkoxylates, oxyethylated and / or oxypropylated derivatives, sugar ethers, polyol esters, such as glycerol, polyethylene glycol, sorbitol and sorbitan, the mono and diethanol amides, carboxylic acid amides, sulfonic acids or amino acids.
- the anionic amphiphilic hydrocarbon compounds are characterized in that they contain one or more functional groups ionizable in the aqueous phase to form negatively charged ions. These anionic groups bringing the surface activity of the molecule.
- Such functional group is an acidic group ionized by a metal or an amine.
- the acid may for example be a carboxylic, sulfonic, sulfuric or phosphoric acid.
- anionic amphiphilic hydrocarbon compounds mention may be made of:
- carboxylates such as metal soaps, alkaline soaps, or organic soaps (such as N-acyl amino acids, N-acyl sarcosinates, N-acyl glutamates and N-acyl polypeptides),
- sulfonates such as alkylbenzenesulphonate (ie alkoxylated alkylbenzene sulphonates), paraffins and olefin sulphonates, ligosulphonates or sulphonuccinic derivatives (such as sulphosuccinates, hemisulfosuccinates, dialkylsulphosuccinates, for example dioctyl sodium sulphosuccinate).
- alkylbenzenesulphonate ie alkoxylated alkylbenzene sulphonates
- paraffins and olefin sulphonates ligosulphonates or sulphonuccinic derivatives (such as sulphosuccinates, hemisulfosuccinates, dialkylsulphosuccinates, for example dioctyl sodium sulphosuccinate).
- sulphates such as alkyl sulphates, alkyl ether sulphates and phosphates.
- the cationic amphiphilic hydrocarbon compounds are characterized in that they contain one or more functional groups ionizable in the aqueous phase to form positively charged ions. These cationic groups bringing the surface activity of the molecule.
- cationic hydrocarbon compounds mention may be made of:
- alkylamine salts such as
- Quaternary ammonium salts such as alkyl trimethylammonium derivatives or tetraalkylammonium derivatives or else alkyl dimethyl benzylammonium derivatives,
- sulfonium or phosphonium derivatives for example tetraalkylphosphonium derivatives.
- heterocyclic derivatives such as pyridinium, imidazolium, quinolinium, piperidinium or morpholinium derivatives.
- the zwitterionic hydrocarbon compounds are characterized in that they possess at least two ionizable groups, such that at least one is positively charged and at least one is negatively charged.
- the groups being chosen from the anionic and cationic groups described above, such as, for example, betaines, alkyl amido betaine derivatives, sulfobetaine, phosphobetaines or even carboxybetaines.
- amphiphilic compounds comprising a neutral, anionic, cationic or zwitterionic hydrophilic part
- a hydrophobic part defined as having a high affinity with the water-immiscible solvent
- silicone, oligomeric or polymeric amphiphilic compounds may also be used for the water / organic solvent or water / halogenated or perhalogenated solvent or water / silicone solvent mixtures.
- the neutral silicone amphiphilic compounds may be oligomers or copolymers of the PDMS type in which the methyl groups are partially replaced by polyalkylene oxide groups (of the polyethylene oxide, propylene polyoxide or a polyoxide-mixed polymer type).
- polyalkylene oxide groups of the polyethylene oxide, propylene polyoxide or a polyoxide-mixed polymer type.
- ethylene and propylene) or pyrrolidone such as PDMS / hydroxyalkyleneoxypropylmethylsiloxane derivatives or alternatively alkylmethylsiloxane / hydroxyalkyleneoxypropylmethylsiloxane derivatives.
- These copolyols obtained by hydrosilylation reaction have reactive hydroxyl end groups. They can therefore be used to carry out ester groups, for example by reacting a fatty acid, or else alkanolamide groups, or even glycoside groups.
- Silicone polymers having lateral (hydrophobic) alkyl groups directly attached to the silicon atom can also be modified by reaction with fluoro (hydrophilic) type molecules to form amphiphilic compounds.
- the surfactant properties are adjusted with the ratio hydrophilic group / hydrophobic group.
- the PDMS copolymers can also be rendered amphiphilic by anionic groups such as phosphate, carboxylate, sulfate or sulphosuccinate groups. These polymers are generally obtained by reaction of acids with the final hydroxyl end groups of alkylene polyoxide side chains of polysiloxane.
- the PDMS copolymers can also be rendered amphiphilic by cationic groups such as quaternary ammonium groups, quaternized alkylamido amine groups, or quaternized alkyl alkoxy amine groups or a quaternized amino imidazoline amine. It is possible to use, for example, the PDMS / benzyltrimethylammoniummethylsiloxane copolymer or the halogeno-N-alkyl-N, N-dimethyl- (3-siloxanylpropyl) ammonium derivatives.
- the PDMS copolymers may also be rendered amphiphilic by betaine-type groups such as carboxybetaine, an alkyl amido betaine, a phosphobetaine or a sulfobetaine.
- the copolymers will comprise a hydrophobic siloxane chain and for example a hydrophilic organobetaine part of general formula: (Me 3 SiO) (SiMe 2 O) 3 (SiMeRO) SiMe 3
- amphiphilic compounds comprising a neutral, anionic, cationic or zwitterionic hydrophilic part, may also have a hydrophobic part (defined as having a high affinity with the water immiscible solvent) halogenated or perhalogenated.
- hydrophobic part defined as having a high affinity with the water immiscible solvent
- amphiphilic compounds halogens, oligomers or polymers can also be used for mixtures water / organic solvent or water / halogenated or perhalogenated solvent or water / silicone solvent.
- Halogenated amphiphilic compounds such as, for example, fluorinated compounds may be ionic or nonionic.
- fluorinated compounds may be ionic or nonionic.
- nonionic amphiphilic halogen or perhalogenated compounds such as the compounds corresponding to the general formula Rf (CH 2 ) (OC 2 H 4 ) n OH, in which Rf is a partially hydrogenated perfluorocarbon or fluorocarbon chain in which n is a whole number at least 1, fluorinated nonionic surfactants of polyoxyethylene-fluoroalkyl ether type,
- ionizable amphiphilic compounds for forming anionic compounds such as perfluorocarboxylic acids, and their salts, or perfluorosulphonic acids and their salts, perfluorophosphate compounds, mono and dicarboxylic acids deriving from perfluoro polyethers, and their salts, mono acids; and disulfonic compounds derived from perfluoro polyethers, and their salts, perfluoro polyether phosphate amphiphilic compounds and perfluoro polyether diphosphate amphiphilic compounds,
- the device comprises a reactor of 1.5 liters of capacity comprising an inlet 11 and an outlet for the gas, a suction 12 and a discharge 13 for the liquid. These liquid inlet and outlet are connected to a circulation loop 14 of 10 meters consisting of tubes of internal diameter equal to 7.7 mm. Tubes of diameter similar to those of the loop ensure the flow of fluids from the loop to the reactor, and vice versa, via a gear pump 15 placed between the two.
- a sapphire cell C integrated in the circuit allows a visualization of the circulating liquid, and therefore hydrates, if they have formed.
- the liquid or liquids (water or water + solvent + additive) are introduced into the reactor at a volume of 1.4 L.
- the plant is then pressurized to 7 MPa. using the study gas. Homogenization of the liquids is ensured by their circulation in the loop and the reactor.
- a rapid temperature decrease of 17 ° C. to 4 ° C. is imposed (temperature below the formation temperature of the hydrates). The temperature is then maintained at this value.
- the duration of the tests can vary from a few minutes to several hours.
- the conversion rate of water to hydrate is calculated and the transportability of the hydrate slurry once formed is studied, when transport is possible. In this case, the pressure drop DP and the flow rate F in the loop are stable.
- Example 1 is given for comparison.
- Example 1 is given for comparison.
- EXAMPLE 2 The procedure is as in Comparative Example 1, but with a fluid composed, by volume, of 10% of water and 90% of solvent to which an amphiphilic compound obtained by reaction between a polyisobutenyl succinic anhydride and polyethylene is added. glycol. The amphiphilic compound is added at a concentration of 0.17% by weight relative to the volume of solvent.
- the weight composition of the solvent is:
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Gas Separation By Absorption (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0702495A FR2914565B1 (en) | 2007-04-05 | 2007-04-05 | PROCESS FOR ENRICHING ACIDIC GASES WITH GASEOUS EFFLUENT |
PCT/FR2008/000457 WO2008142262A2 (en) | 2007-04-05 | 2008-04-03 | Process for enriching a gaseous effluent with acid gases |
Publications (1)
Publication Number | Publication Date |
---|---|
EP2142283A2 true EP2142283A2 (en) | 2010-01-13 |
Family
ID=38720375
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP08787896A Withdrawn EP2142283A2 (en) | 2007-04-05 | 2008-04-03 | Process for enriching a gaseous effluent with acid gases |
Country Status (6)
Country | Link |
---|---|
US (1) | US20100200809A1 (en) |
EP (1) | EP2142283A2 (en) |
JP (1) | JP5096555B2 (en) |
CA (1) | CA2681245A1 (en) |
FR (1) | FR2914565B1 (en) |
WO (1) | WO2008142262A2 (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2228117B1 (en) * | 2009-02-25 | 2015-04-15 | Siemens Aktiengesellschaft | Absorber liquid, method for producing same and application of same |
EP2228118A1 (en) * | 2009-02-25 | 2010-09-15 | Siemens Aktiengesellschaft | Absorber liquid, method for producing same and application of same |
JP5489150B2 (en) * | 2009-02-26 | 2014-05-14 | 学校法人日本大学 | Production method of clathrate hydrate |
FR2960447B1 (en) * | 2010-05-27 | 2012-07-20 | Inst Francais Du Petrole | PROCESS FOR ENRICHING ACIDIC GASES WITH GASEOUS EFFLUENT |
FR2976190B1 (en) | 2011-06-10 | 2013-06-28 | IFP Energies Nouvelles | METHOD OF CAPTURING ACIDIC COMPOUNDS BY FORMATION OF HYDRATES WITH A DEMIXING STEP. |
WO2015091477A1 (en) * | 2013-12-20 | 2015-06-25 | Solvay Specialty Polymers Italy S.P.A. | Method for removing carbon dioxide from gas mixtures |
CN106566494B (en) * | 2016-11-07 | 2020-02-04 | 天津天诚拓源科技发展有限公司 | High-temperature-resistant fluid loss additive for oil-based drilling fluid and preparation method thereof |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2625547B1 (en) * | 1987-12-30 | 1990-06-22 | Inst Francais Du Petrole | PROCESS FOR DELAYING FORMATION AND / OR REDUCING THE TENDENCY TO AGGLOMERATION OF HYDRATES |
JPH06205937A (en) * | 1993-01-11 | 1994-07-26 | Ishikawajima Harima Heavy Ind Co Ltd | Flue gas decarboxylation device |
US5434330A (en) * | 1993-06-23 | 1995-07-18 | Hnatow; Miguel A. | Process and apparatus for separation of constituents of gases using gas hydrates |
US6106595A (en) * | 1996-04-30 | 2000-08-22 | Spencer; Dwain F. | Methods of selectively separating CO2 from a multicomponent gaseous stream |
JP3983910B2 (en) * | 1998-11-12 | 2007-09-26 | 千代田化工建設株式会社 | Method for producing gas hydrate |
US7128777B2 (en) * | 2004-06-15 | 2006-10-31 | Spencer Dwain F | Methods and systems for selectively separating CO2 from a multicomponent gaseous stream to produce a high pressure CO2 product |
JP4930963B2 (en) * | 2005-04-25 | 2012-05-16 | 独立行政法人産業技術総合研究所 | Continuous gas separation method and apparatus using hydrate generation by static mixer |
JP5334279B2 (en) * | 2007-03-19 | 2013-11-06 | 東京瓦斯株式会社 | Gas clathrate production accelerator and gas clathrate production method |
FR2960447B1 (en) * | 2010-05-27 | 2012-07-20 | Inst Francais Du Petrole | PROCESS FOR ENRICHING ACIDIC GASES WITH GASEOUS EFFLUENT |
-
2007
- 2007-04-05 FR FR0702495A patent/FR2914565B1/en not_active Expired - Fee Related
-
2008
- 2008-04-03 US US12/594,627 patent/US20100200809A1/en not_active Abandoned
- 2008-04-03 EP EP08787896A patent/EP2142283A2/en not_active Withdrawn
- 2008-04-03 WO PCT/FR2008/000457 patent/WO2008142262A2/en active Application Filing
- 2008-04-03 CA CA002681245A patent/CA2681245A1/en not_active Abandoned
- 2008-04-03 JP JP2010501551A patent/JP5096555B2/en not_active Expired - Fee Related
Non-Patent Citations (1)
Title |
---|
See references of WO2008142262A2 * |
Also Published As
Publication number | Publication date |
---|---|
WO2008142262A3 (en) | 2009-02-19 |
FR2914565B1 (en) | 2009-05-22 |
JP2010523310A (en) | 2010-07-15 |
FR2914565A1 (en) | 2008-10-10 |
US20100200809A1 (en) | 2010-08-12 |
WO2008142262A2 (en) | 2008-11-27 |
CA2681245A1 (en) | 2008-11-27 |
JP5096555B2 (en) | 2012-12-12 |
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