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WO2011006695A1 - Extraction de métaux étrangers contenus dans des silanes inorganiques - Google Patents

Extraction de métaux étrangers contenus dans des silanes inorganiques Download PDF

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Publication number
WO2011006695A1
WO2011006695A1 PCT/EP2010/056714 EP2010056714W WO2011006695A1 WO 2011006695 A1 WO2011006695 A1 WO 2011006695A1 EP 2010056714 W EP2010056714 W EP 2010056714W WO 2011006695 A1 WO2011006695 A1 WO 2011006695A1
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WO
WIPO (PCT)
Prior art keywords
foreign metal
metal
containing compound
silane
foreign
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.)
Ceased
Application number
PCT/EP2010/056714
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German (de)
English (en)
Inventor
Ekkehard MÜH
Hartwig Rauleder
Jaroslaw Monkiewicz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Evonik Operations GmbH
Original Assignee
Evonik Degussa GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Evonik Degussa GmbH filed Critical Evonik Degussa GmbH
Priority to EP10720760A priority Critical patent/EP2454194A1/fr
Priority to JP2012519942A priority patent/JP5653427B2/ja
Publication of WO2011006695A1 publication Critical patent/WO2011006695A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B33/00—Silicon; Compounds thereof
    • C01B33/08—Compounds containing halogen
    • C01B33/107—Halogenated silanes
    • C01B33/10778—Purification
    • C01B33/10784—Purification by adsorption
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/80—Compositional purity

Definitions

  • the invention relates to a process for the treatment of a composition containing inorganic silanes and at least one foreign metal and / or a
  • a foreign metal-containing compound wherein the composition is contacted with at least one organic, amino-functionalized, polymeric adsorbent, in particular an organic aminoalkyl-functionalized polymeric adsorbent, and recovering the composition in which the content of the foreign metal and / or the foreign metal-containing compound is reduced and the
  • Silicon compounds used in microelectronics such as
  • Silicon nitride (SiN), silicon oxide (SiO), silicon oxynitride (SiON), silicon oxycarbide (SiOC) or silicon carbide (SiC) have to fulfill very high purity requirements. This is especially true in the production of thin layers of these materials. In chip production, contamination of the silicon compounds with metallic impurities results in undesirable doping of the epitaxial layers, e.g. Epitaxial silicon layers.
  • silicon tetrachloride SiCl 4
  • SiCI 4 is required in very high purity.
  • halosilanes and / or hydrogenhalosilanes are higher Purity, in the field of electronics, the semiconductor industry as well as in the pharmaceutical industry wished starting compounds.
  • tetrachlorosilane or trichlorosilane of silicon usually also has the chlorinated impurities present in silicon, which are sometimes carried off into the subsequent synthesis steps.
  • these chlorinated metallic impurities have a disadvantageous effect in the production of components in the field of electronics.
  • WO 2009049944 A1 discloses a method for the reduction of metals or semi-metals such as iron, aluminum, and boron, from trichlorosilane with Amberlite ® XAD-4 resin or montmorillonite K 10 TM.
  • Amberlite ® XAD-4 is a divinylbenzene cross-linked polystyrene with no functional groups and montmorillonite is a clay mineral that belongs to the phyllosilicates.
  • the content of boron and iron should be reduced inexpensively and easily handled in inorganic silanes.
  • Adsorbent in particular an alkylamino-functionalized, polymeric
  • the adsorbent is used according to the invention substantially anhydrous and / or free of organic solvents for the treatment of the composition. It is further preferred when the substantially water-free and solvent-free adsorbent such as Amberlyst ® A21 is inserted into the reactor to treat the composition.
  • the conversion into the reactor can preferably be carried out under an inert gas atmosphere, such as under nitrogen, argon or alternatively under dry air. Preference may also be given to using a mixture of said adsorbents or with further adsorbents in order to obtain an optimum
  • the adsorbent is preferably used purified so as not to contribute to contamination by additional impurities.
  • the abovementioned high-purity adsorbents are used in the process according to the invention.
  • Adsorbents which can be used at the same time as catalysts or have been used and are consumed can also be used appropriately
  • inventive methods are used, provided that they do not contribute to any additional contamination of the treated compositions.
  • the invention therefore relates to a method for the treatment of a
  • composition with at least one organic amino-functionalized, in particular aminoalkylfunktionalformaten, polymeric adsorbent is brought into contact and a composition is obtained, the content of
  • Foreign metal and / or at least one foreign metal-containing compound is reduced. It is of particular advantage that the foreign metal content and / or the content of the foreign metal-containing compound, - is usually a residual content of foreign metal or foreign metal-containing
  • the degree of reduction of the foreign metal content is also determined by the ratio of adsorbent to composition and the contact time. The person skilled in the art knows how to determine the optimum treatment conditions.
  • the adsorbent according to the invention is outstandingly suitable for the adsorptive separation of distillatively poorly separable foreign metal-containing compounds which dissolve in the composition or are completely dissolved therein.
  • the adsorptive separation of the foreign metal-containing compounds is believed to occur by complex formation of the foreign metal-containing compound and the adsorbent. Particulate foreign metals are presumably retained mechanically by the adsorbent.
  • the determination of the foreign metals or of the foreign metal-containing compounds can generally be carried out by quantitative analysis methods, as known to those skilled in the art, for example by atomic absorption spectroscopy (AAS) or photometry, in particular by inductively coupled plasma mass spectrometry (ICP -MS) and Inductively Coupled Plasma Optical Emission Spectrometry (ICP-OES) - to name but a few.
  • AAS atomic absorption spectroscopy
  • ICP -MS inductively coupled plasma mass spectrometry
  • ICP-OES Inductively Coupled Plasma Optical Emission Spectrometry
  • Adsorbent is essentially anhydrous and solvent-free. About Karl-Fischer (DIN 51 777), the water content in the adsorbent can be determined and the solvent content, for example by means of TGA-MS, TGA-IR or other, the
  • Solvents are alcohols, such as methanol, ethanol, or acetone and aromatic solvents, such as toluene.
  • An essentially adsorbent whose water content or solvent content of organic solvents is in each case less than 2.5% by weight to, for example, 0.0001% by weight, in particular less than 1, with respect to the total weight of the adsorbent is regarded as substantially anhydrous and / or solvent-free , 5 wt .-%, preferably less than 1, 0 wt .-%, preferably less than 0.5 wt .-%, particularly preferably 0.3 wt .-%, better less than 0.1 or ideally less than 0.01 wt. % to the detection limit, for example up to 0.0001% by weight.
  • Inorganic silane is understood to mean, in particular, halosilanes, hydrohalosilanes, halosilanes which are substituted by at least one organic radical and / or hydrohalosilanes which are substituted by at least one organic radical and also mixtures comprising at least one of these silanes.
  • pure hydrogen silanes may also be included.
  • each halogen independently of other halogen atoms can be selected from the group fluorine, chlorine, bromine or iodine, so that, for example, mixed halosilanes such as SiBrCI 2 F or SiBr 2 CIF can be included.
  • the inorganic silanes preferably include the chlorine-substituted silanes, predominantly monomeric silanes, such as, for example, tetrachlorosilane, trichlorosilane, dichlorosilane, monochlorosilane, methyltrichlorosilane, trichloromethylsilane,
  • Trimethylchlorosilane dimethyldichlorosilane, phenylmethyldichlorosilane, phenyltrichlorosilane, vinyltrichlorosilane, dihydrodichlorosilane.
  • monomeric silanes such as tetramethylsilane, trimethylsilane, dimethylsilane, methylsilane, monosilane or
  • Organohydrogensilanes or also disilane, trisilane, tetrasilane and / or pentasilane and higher homologous silanes can be reduced in their foreign metal content according to the method according to the invention.
  • Pentachlorhydrogendisilan or Tetrachlordihydrogendisilan and
  • the cyclic oligomeric inorganic silanes include compounds of the type Si n X 2n, with n> 3, such as Si 5 CliO, and to the polymeric inorganic compounds, for example, halopolysilanes, ie
  • a halogen such as F, Cl, Br, J, especially Cl.
  • the process according to the invention is particularly suitable for the treatment of
  • foreign metals and / or foreign metal-containing compounds are considered those in which the metal or semimetal does not correspond to silicon.
  • Adsorption of the at least one foreign metal and / or the foreign metal-containing compound is carried out in particular selectively from the inorganic silane-containing composition, while the adsorption can be carried out both in solution and in the gas phase.
  • foreign metals or foreign metal-containing compounds are also understood half metals or compounds containing semimetals, such as boron and boron trichloride.
  • the foreign metals and / or foreign metal-containing compounds to be reduced are metal halides
  • Examples include aluminum trichloride or iron (III) -chlohd as well as entrained particulate metals, which can come from continuous processes.
  • Magnesium, calcium and / or iron are reduced, particularly preferably, the content of boron and iron in the composition or in the inorganic silane be significantly reduced, in particular, based on these metals
  • the inventive method is particularly suitable for the separation or
  • Azeotrope would pass. These foreign metal-containing compounds can sometimes be difficult to remove by distillation or not at all.
  • a boiling point which is in the range of the boiling point of an inorganic silane compound, a boiling point is considered, which is in the range of ⁇ 20 0 C of the boiling point of one of the inorganic silanes at atmospheric pressure (about 1013.25 hPa or 1013.25 mbar).
  • the compounds to be adsorbed are distinguished by the fact that they are generally completely dissolved in the composition and can only be separated off poorly by distillation.
  • Compound be reduced by 50 to 99 wt .-%.
  • the st .-% Preferably, the
  • the process allows a reduction of the residual content by 70 wt .-%, preferably 95 to 99 wt .-%.
  • the iron content of a composition of inorganic silanes by 50 to 99 wt .-%, preferably 70 to 99 wt .-% and the boron content by at least 90 wt .-%, preferably by 95 to 99.5 wt .-% be reduced, especially in one process step.
  • the foreign metal content and / or the content of the foreign metal-containing compound in a composition may preferably be in the range from below 100 ⁇ g / kg to the detection limit, in particular below 25 ⁇ g / kg, with respect to the metallic compound, in particular independently , preferably below 15 ⁇ g / kg, more preferably 0.1 to 10 ⁇ g / kg, down to the respective limit of detection.
  • the alkyl groups may be linear, branched or cyclic, preferably methyl or ethyl.
  • amino-functionalized divinylbenzene-styrene copolymers can be used, i. H. Divinylbenzene crosslinked polystyrene resins, wherein the from the group of dialkylamino or dialkylaminomethylenfunktionalinstrumenten divinylbenzene-styrene copolymers or thalkylammonium- or trialkylammoniummethylen- functionalized divinylbenzene-styrene copolymers are particularly preferred, in particular with alkyl is methyl or ethyl, preferably dimethyl- or trimethylaminomethyl-functionalized copolymers.
  • porous polystyrene resins for the treatment of inorganic silanes can be used.
  • Adsorbents are all characterized by a high specific surface area and porosity.
  • Polystyrene ie divinylbenzene-styrene copolymer
  • a ⁇ is independently an anion, for example but not limited to the series OH ⁇ (hydroxy), Cl “ (chloride), CH 3 COO " (acetate) or HCOO " (formate) is, in particular OH ⁇
  • Adsorbents such as Amberlyst ® A 21 an ion exchange resin based on cross-linked polystyrene divinylbenzene resin having dimethylamino groups on the polymeric backbone of the resin.
  • Amberlyst ® A21 is a weakly basic
  • Anion exchange resin which can be purchased in the form of free base and in spherical beads having an average diameter of about 0.49 to 0.69 mm and a water content of up to 54 to 60 wt .-% in relation to the total weight.
  • the surface area is about 25 m 2 / g and the mean pore diameter is 400
  • Amberlyst ® A 26 OH which is based on a quaternary trimethylammonium functionalized divinylbenzene-styrene copolymer and having a highly porous structure can be used for treatment according to the invention in the process.
  • the average particle diameter of the adsorbent is usually 0.5 to 0.7 mm.
  • the resin is sold as an ionic form (called “hydroxide” form, "OH").
  • the water content may be 66 to 75% by weight based on the total weight.
  • the surface area is about 30 m 2 / g with an average pore diameter of 290 angstroms.
  • the treatment according to the invention will be at least one
  • inorganic silane-containing compositions carried out such that first the adsorbent is dried thoroughly to prevent hydrolysis of the silanes to be purified.
  • the drying of the adsorbent is preferably carried out under vacuum, for example at elevated temperature and below 175 0 C.
  • the dried adsorbent for example, under an inert gas atmosphere in the reactor, and brought into contact with the composition, optionally stirred.
  • the treatment is carried out at room temperature and atmospheric pressure for several hours.
  • the composition is contacted with the adsorbent for between 1 minute to 10 hours, typically up to 5 hours.
  • the recovery or separation of the purified composition is usually carried out by filtration, centrifugation or sedimentation.
  • the pretreatment of the absorbent takes place outside the reactor, thereby indicating the use of organic
  • Solvents are not needed for cleaning the adsorbent and for removing adhering water.
  • the process of the treatment can be discontinuous or continuous as needed.
  • the treatment can be carried out in a reactor, for example with stirring, or in a continuous
  • Treatment may include treatment in a flow-through reactor, e.g. B. one
  • Inorganic silane has a reduced by 50 to 99 wt .-% of foreign metal content and / or content of foreign metal-containing compound.
  • the invention likewise provides a method for treating a
  • composition comprising at least one inorganic silane and at least one foreign metal and / or a foreign metal-containing compound, according to the above described method, wherein at least one inorganic silane corresponds to the general formula I,
  • the treatment of trichlorosilane is optionally carried out in mixtures with monosilane, dichlorosilane and / or tetrachlorosilane in a continuously operated reactor.
  • the method is also suitable for the treatment of compositions containing compounds of the type of general formula I,
  • aryl group also alkyl-substituted aryls, with linear, branched or cyclic alkyl groups having 1 to 8 carbon atoms, understood.
  • n 3, 0 ⁇ a ⁇ 8, O ⁇ b ⁇ 8, where the substitution pattern of X and R may be as listed above.
  • the foreign metal content and / or the content of the foreign metal-containing compound of this composition may preferably in each case with respect to the metallic compound, in each case to a content in the range of below 100 ug / kg, in particular of less than 75 ug / kg, preferably below 25 ⁇ g / kg, preferably below 15 ⁇ g / kg, more preferably below 10 ⁇ g / kg.
  • the invention also provides the use of an organic compound
  • amino-functionalized polymeric adsorbent for reducing the content of at least one foreign metal and / or at least one foreign metal-containing compound from compositions comprising at least one inorganic silane, in particular a silane of the general formula I,
  • the use for reducing the content is at least one
  • Foreign metal and / or at least one foreign metal-containing compound comprising compositions comprising at least one silane selected from monosilane, monochlorosilane, dichlorosilane, trichlorosilane, tetrachlorosilane, methyltrichlorosilane,
  • the use is preferably carried out in a continuously operated reactor.
  • the adsorbent is used substantially anhydrous and solvent-free, in particular by being optionally washed with ultrapure water as described above and subsequently treated under vacuum and / or elevated temperature.
  • the adsorbents are carefully dried prior to use in the process to prevent hydrolysis of the silanes to be purified.
  • a defined amount of adsorbent is placed in a 500 ml stirred apparatus comprising a glass four-necked flask with condenser (water, dry ice), dropping funnel, stirrer, thermometer and nitrogen inlet and under vacuum ( ⁇ 1 mbar) (rotary vane pump) and at 95 0 C. dried over 5 hours, then slowly aerated with dry nitrogen and cooled.
  • condenser water, dry ice
  • dropping funnel stirrer
  • thermometer and nitrogen inlet and under vacuum ⁇ 1 mbar
  • rotary vane pump rotary vane pump
  • the adsorbent is separated from the silane by passing it through a frit (Por. 4) into an evacuated 500 ml glass flask with a vent. Subsequently, the glass flask is vented with nitrogen and flushed with nitrogen
  • Amberlite ® XAD4 used in Comparative Example is based on cross-linked polystyrene with divinylbenzene, and in the form of small beads (mean 0 0.5 mm) is supplied wasserbefeuchtet.
  • Amberlite XAD4 ® has no additional functional groups on the polymeric backbone on, it is suitable, as outlined in the above reference, as adsorbent for the separation of metallic contaminants from chlorosilanes. The ability to adsorb is due to the absence of further functional groups due to the porous structure or interactions with the aromatic-rich polymer backbone.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Silicon Compounds (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé de traitement d'une composition contenant au moins un silane inorganique et au moins un métal étranger et/ou un composé contenant un métal étranger. Le procédé consiste à mettre la composition en contact avec un agent d'adsorption polymère, aminofonctionnel, organique, et à obtenir une composition dans laquelle la teneur en métal étranger et/ou en composé contenant le métal étranger est réduite. L'invention concerne également l'utilisation de l'agent d'adsorption pour la réduction de métaux étrangers et/ou de composés contenant des métaux étrangers dans des compositions de silanes inorganiques.
PCT/EP2010/056714 2009-07-15 2010-05-17 Extraction de métaux étrangers contenus dans des silanes inorganiques Ceased WO2011006695A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP10720760A EP2454194A1 (fr) 2009-07-15 2010-05-17 Extraction de métaux étrangers contenus dans des silanes inorganiques
JP2012519942A JP5653427B2 (ja) 2009-07-15 2010-05-17 無機シランからの異種金属の除去

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200910027729 DE102009027729A1 (de) 2009-07-15 2009-07-15 Entfernung von Fremdmetallen aus anorganischen Silanen
DE102009027729.3 2009-07-15

Publications (1)

Publication Number Publication Date
WO2011006695A1 true WO2011006695A1 (fr) 2011-01-20

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EP (1) EP2454194A1 (fr)
JP (1) JP5653427B2 (fr)
DE (1) DE102009027729A1 (fr)
TW (1) TW201125821A (fr)
WO (1) WO2011006695A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9221689B2 (en) 2011-02-14 2015-12-29 Evonik Degussa Gmbh Monochlorosilane, process and apparatus for the preparation thereof
WO2016037601A1 (fr) * 2014-09-08 2016-03-17 Psc Polysilane Chemicals Gmbh Procédé de purification d'oligosilanes halogénés
CN108408729A (zh) * 2018-05-02 2018-08-17 西安蓝深环保科技有限公司 一种三氯氢硅中分离重金属的方法
WO2022096098A1 (fr) * 2020-11-05 2022-05-12 Wacker Chemie Ag Procédé d'élimination d'une impureté d'un mélange de chlorosilane
US12209019B2 (en) 2018-11-28 2025-01-28 Hysilabs, Sas Catalysed process of production of hydrogen from silylated derivatives as hydrogen carrier compounds

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102014206875A1 (de) * 2014-04-09 2015-10-15 Wacker Chemie Ag Verfahren zur Reinigung von technischen Anlagenteilen von Metallhalogeniden
DE102016206090A1 (de) 2016-04-12 2017-10-12 Wacker Chemie Ag Verfahren zur Abtrennung von Aluminiumchlorid aus Silanen
DE102016014900A1 (de) 2016-12-15 2018-06-21 Psc Polysilane Chemicals Gmbh Verfahren zur Erhöhung der Reinheit von Oligosilanen und Oligosilanverbindungen
KR102072547B1 (ko) * 2018-01-26 2020-02-04 오션브릿지 주식회사 헥사클로로디실란의 정제 방법
EP4017861B8 (fr) 2019-08-22 2023-08-16 Dow Silicones Corporation Procédé de purification de composés de silicium

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US2877097A (en) * 1958-05-06 1959-03-10 Guenter A Wolff Method of purification of silicon compounds
US3414603A (en) * 1965-03-16 1968-12-03 Tyco Laboratories Inc Method of purifying organochlorosilanes
DE2852598A1 (de) 1977-12-05 1979-06-07 Smiel Spa Verfahren zur reinigung von chlorsilanen
US4676967A (en) * 1978-08-23 1987-06-30 Union Carbide Corporation High purity silane and silicon production
US4713230A (en) * 1982-09-29 1987-12-15 Dow Corning Corporation Purification of chlorosilanes
DE10057482A1 (de) * 2000-11-20 2002-05-23 Solarworld Ag Verfahren zur Reinigung von Trichlorsilan
US20050054211A1 (en) * 2003-09-04 2005-03-10 Mindi Xu Purification of silicon-containing materials
DE102007050199A1 (de) * 2007-10-20 2009-04-23 Evonik Degussa Gmbh Entfernung von Fremdmetallen aus anorganischen Silanen

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US2877097A (en) * 1958-05-06 1959-03-10 Guenter A Wolff Method of purification of silicon compounds
US3414603A (en) * 1965-03-16 1968-12-03 Tyco Laboratories Inc Method of purifying organochlorosilanes
DE2852598A1 (de) 1977-12-05 1979-06-07 Smiel Spa Verfahren zur reinigung von chlorsilanen
US4224040A (en) * 1977-12-05 1980-09-23 Smiel S.P.A. Process for the purification of chlorosilanes
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DE10057482A1 (de) * 2000-11-20 2002-05-23 Solarworld Ag Verfahren zur Reinigung von Trichlorsilan
US20050054211A1 (en) * 2003-09-04 2005-03-10 Mindi Xu Purification of silicon-containing materials
DE102007050199A1 (de) * 2007-10-20 2009-04-23 Evonik Degussa Gmbh Entfernung von Fremdmetallen aus anorganischen Silanen
WO2009049944A1 (fr) 2007-10-20 2009-04-23 Evonik Degussa Gmbh Élimination de métaux exogènes contenus dans des silanes inorganiques

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9221689B2 (en) 2011-02-14 2015-12-29 Evonik Degussa Gmbh Monochlorosilane, process and apparatus for the preparation thereof
WO2016037601A1 (fr) * 2014-09-08 2016-03-17 Psc Polysilane Chemicals Gmbh Procédé de purification d'oligosilanes halogénés
US10457559B2 (en) 2014-09-08 2019-10-29 Psc Polysilane Chemicals Gmbh Method for purifying halogenated oligosilanes
CN108408729A (zh) * 2018-05-02 2018-08-17 西安蓝深环保科技有限公司 一种三氯氢硅中分离重金属的方法
US12209019B2 (en) 2018-11-28 2025-01-28 Hysilabs, Sas Catalysed process of production of hydrogen from silylated derivatives as hydrogen carrier compounds
WO2022096098A1 (fr) * 2020-11-05 2022-05-12 Wacker Chemie Ag Procédé d'élimination d'une impureté d'un mélange de chlorosilane
CN115023407A (zh) * 2020-11-05 2022-09-06 瓦克化学股份公司 用于从氯硅烷混合物中除去杂质的方法
CN115023407B (zh) * 2020-11-05 2024-05-24 瓦克化学股份公司 用于从氯硅烷混合物中除去杂质的方法
US12391559B2 (en) 2020-11-05 2025-08-19 Wacker Chemie Ag Process for removing an impurity from a chlorosilane mixture

Also Published As

Publication number Publication date
EP2454194A1 (fr) 2012-05-23
JP5653427B2 (ja) 2015-01-14
TW201125821A (en) 2011-08-01
DE102009027729A1 (de) 2011-01-27
JP2012532827A (ja) 2012-12-20

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