US20080210566A1 - Electrochemical Deposition of Selenium in Ionic Liquids - Google Patents
Electrochemical Deposition of Selenium in Ionic Liquids Download PDFInfo
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- US20080210566A1 US20080210566A1 US12/088,130 US8813006A US2008210566A1 US 20080210566 A1 US20080210566 A1 US 20080210566A1 US 8813006 A US8813006 A US 8813006A US 2008210566 A1 US2008210566 A1 US 2008210566A1
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- hydroxyethyl
- hydroxybutyl
- imidazolium
- methyl
- hydroxypropyl
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- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25D—PROCESSES FOR THE ELECTROLYTIC OR ELECTROPHORETIC PRODUCTION OF COATINGS; ELECTROFORMING; APPARATUS THEREFOR
- C25D3/00—Electroplating: Baths therefor
- C25D3/66—Electroplating: Baths therefor from melts
- C25D3/665—Electroplating: Baths therefor from melts from ionic liquids
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- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25D—PROCESSES FOR THE ELECTROLYTIC OR ELECTROPHORETIC PRODUCTION OF COATINGS; ELECTROFORMING; APPARATUS THEREFOR
- C25D3/00—Electroplating: Baths therefor
- C25D3/02—Electroplating: Baths therefor from solutions
- C25D3/54—Electroplating: Baths therefor from solutions of metals not provided for in groups C25D3/04 - C25D3/50
Definitions
- the invention relates to a process for the electrochemical deposition of selenium on a substrate in an ionic liquid.
- Selenium has a number of properties which make it suitable for many areas of application in photovoltaics and electronics.
- Selenium is a photosemiconductor which changes (increases) its conductivity by a number of orders of magnitude on exposure to visible light.
- selenium is transparent to wavelengths greater than 650 nm.
- Selenium is often employed as a constituent in thin-film solar cells in combination with Cu and indium, as described, for example, in DE 44 47 866 or in DE 199 177 58.
- the production processes usually mentioned for the production of these systems either all film components are deposited by evaporation processes or only copper or indium is applied by electroplating. In both cases, the selenium is preferably applied via the gas phase in an evaporator.
- Electrochemical deposition of copper indium gallium diselenide is described in US 2004/0206390.
- the electrochemical deposition there is carried out in a buffered bath comprising potassium biphthalate and amidosulfuric acid.
- the said components are said to scavenge H + and OH ⁇ ions formed by electrolysis.
- the said process is overall unsuitable for the deposition of a single selenium phase.
- the electrolytic deposition of selenium is described in U.S. Pat. No. 2,414,438.
- the deposition is carried out in aqueous alkaline solutions of ammonium selenides, alkali metal selenides or alkaline earth metal selenides.
- the deposition is made more difficult since amorphous or glass-like red selenium, which has poor electron conductivity, is usually deposited in the room-temperature region. Only at elevated temperature is a grey, metallic phase deposited, but the deposits do not consist uniquely of grey selenium, even at temperatures around 100° C. Higher temperatures, which would promote the deposition of grey selenium, are excluded in open electroplating baths. However, the electrochemical deposition would facilitate continuous operation in the form of vat electroplating without closed evaporators or sputtering devices.
- the object of the invention was to find an alternative method for the electrochemical deposition of grey selenium.
- the object is achieved by the process according to the invention.
- the invention relates to a process for the electrochemical deposition of grey selenium on a substrate in at least one ionic liquid.
- the deposition of grey selenium is carried out on a very wide variety of substrates in a very wide variety of applications.
- the deposition can serve exclusively for the deposition of selenium, but can also be employed in combination with the deposition of further materials, such as, for example, copper or indium.
- the ionic liquids which are suitable for the process according to the invention are highly conductive and are generally thermally stable up to 400° C.
- ionic liquids which are electrochemically stable under the deposition conditions described below They have, for example, an electrochemical window in the cathodic branch which extends from 0 mV to ⁇ 3500 mV against ferrocene/ferrocinium, preferably from ⁇ 2000 mV to ⁇ 3000 mV against ferrocene/ferrocinium.
- suitable ionic liquids have an electrochemical window which extends from 0 mV to +3500 mv against ferrocene/ferrocinium, preferably from +2000 to +3000 mV against ferrocene/ferrocinium.
- the data relate to the measurement arrangements and conditions described below.
- Suitable ionic liquids contain, in particular, at least one tetraalkylammonium or tetraalkylphosphonium cation, where the alkyl groups may each, independently of one another, have 1 to 10 C atoms, or a heterocyclic cation selected from
- R 1 ′ to R 4 ′ each, independently of one another, denote
- R 1 ′, R 2 ′, R 3 ′ and/or R 4 ′ together may also form a ring system
- substituents R 1 ′, to R 4 ′ may be partially or fully substituted by halogens, in particular —F and/or —Cl, or —OR′, —CN, —C(O)OH, —C(O)NR′ 2 , —SO 2 NR′ 2 , —C(O)X, —SO 2 OH, —SO 2 X, —NO 2 , but where R 1 ′ and R 4 ′ cannot simultaneously be fully substituted by halogens, and where one or two non-adjacent and non-heteroatom-bonded carbon atoms of the substituents R 1 ′ to R 4 ′ may be replaced by atoms and/or atomic groups selected from —O—, —S—, —S(O)—, —SO 2 —, —C(O)—, —N + R′ 2 —, —C(O)NR′—, —SO 2 NR′—, —P(O)(
- R 2 ′ or R 3 ′ is in each case, independently of one another, in particular hydrogen, methyl, ethyl, isopropyl, propyl, butyl, sec-butyl, tert-butyl, cyclohexyl, phenyl or benzyl.
- R 2 ′ is particularly preferably hydrogen, methyl, ethyl, isopropyl, propyl, butyl or secbutyl.
- R 2 ′ and R 3 ′ are very particularly preferably hydrogen.
- the C 1 -C 12 -alkyl group is, for example, methyl, ethyl, isopropyl, propyl, butyl, sec-butyl or tert-butyl, furthermore also pentyl, 1-, 2- or 3-methylbutyl, 1,1-, 1,2- or 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl or dodecyl.
- a straight-chain or branched alkenyl having 2 to 20 C atoms, in which, in addition, a plurality of double bonds may be present, is, for example, allyl, 2- or 3-butenyl, isobutenyl, sec-butenyl, furthermore 4-pentenyl, isopentenyl, hexenyl, heptenyl, octenyl, —C 9 H 17 , —C 10 H 19 to —C 20 H 39 ; preferably allyl, 2- or 3-butenyl, isobutenyl, sec-butenyl, preference is furthermore given to 4-pentenyl, isopentenyl or hexenyl.
- a straight-chain or branched alkynyl having 2 to 20 C atoms, in which, in addition, a plurality of triple bonds may be present, is, for example, ethynyl, 1- or 2-propynyl, 2- or 3-butynyl, furthermore 4-pentynyl, 3-pentynyl, hexynyl, heptynyl, octynyl, —C 9 H 15 , —C 10 H 17 to —C 20 H 37 , preferably ethynyl, 1- or 2-propynyl, 2- or 3-butynyl, 4-pentynyl, 3-pentynyl or hexynyl.
- Aryl-C 1 -C 6 -alkyl denotes, for example, benzyl, phenylethyl, phenylpropyl, phenylbutyl, phenylpentyl or phenylhexyl, where both the phenyl ring and also the alkylene chain may, as described above, be partially or fully substituted by halogens, in particular —F and/or —Cl, or partially by —OR′, —CN, —C(O)OH, —C(O)NR′ 2 , —SO 2 NR′ 2 , —C(O)X, —SO 2 OH, —SO 2 X, —NO 2 .
- Unsubstituted saturated or partially or fully unsaturated cycloalkyl groups having 3-7 C atoms are therefore cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclopenta-1,3-dienyl, cyclohexenyl, cyclohexa-1,3-dienyl, cyclohexa-1,4-dienyl, phenyl, cycloheptenyl, cyclohepta-1,3-dienyl, cyclohepta-1,4-dienyl or cyclohepta-1,5-dienyl, each of which may be substituted by C 1 — to C 6 -alkyl groups, where the cycloalkyl group or the cycloalkyl group which is substituted by C 1 — to C 6 -alkyl groups may in turn also be substituted by hal
- substituents R 1 ′ to R 4 ′ modified in this way are: —OCH 3 , —OCH(CH 3 ) 2 , —CH 2 OCH 3 , —CH 2 —CH 2 —O—CH 3 , —C 2 H 4 OCH(CH 3 ) 2 , —C 2 H 4 SC 2 H 5 , —C 2 H 4 SCH(CH 3 ) 2 , —S(O)CH 3 , —SO 2 CH 3 , —SO 2 C 6 H 5 , —SO 2 C 3 H 7 , —SO 2 CH(CH 3 ) 2 , —SO 2 CH 2 CF 3 , —CH 2 SO 2 CH 3 , —O—C 4 H 8 —O—C 4 H 9 , —CF 3 , —C 2 F 5 , —C 3 F 7 , —C 4 F 9 , —C(CF 3 ) 3 , —CF 2 SO 2 CF 3
- C 3 — to C 7 -cycloalkyl is, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl.
- substituted phenyl denotes phenyl which is substituted by C 1 — to C 6 -alkyl, C 1 — to C 6 -alkenyl, NO 2 , F, Cl, Br, I, C 1 -C 6 -alkoxy, SCF 3 , SO 2 CF 3 , COOH, SO 2 X′, SO 2 NR′′ 2 or SO 3 H, where X′ denotes F, Cl or Br and R′′ denotes a non-, partially or perfluorinated C 1 — to C 6 -alkyl or C 3 — to C 7 -cycloalkyl as defined for R′, for example, o-, m- or p-methylphenyl, o-, m- or p-ethylphenyl, o-, m- or p-propylphenyl, o-, m- or p-isopropylphenyl, o-, m- or p-
- heteroaryl is taken to mean a saturated or unsaturated mono- or bicyclic heterocyclic radical having 5 to 13 ring members, where 1, 2 or 3 N and/or 1 or 2 S or O atoms may be present and the heterocyclic radical may be mono- or polysubstituted by C 1 — to C 6 -alkyl, C 1 — to C 6 -alkenyl, NO 2 , F, Cl, Br, I, C 1 -C 6 -alkoxy, SCF 3 , SO 2 CF 3 , COOH, SO 2 X′, SO 2 NR′′ 2 or SO 3 H, where X′ and R′′ have a meaning indicated above.
- the heterocyclic radical is preferably substituted or unsubstituted 2- or 3-furyl, 2- or 3-thienyl, 1-, 2- or 3-pyrrolyl, 1-, 2-, 4- or 5-imidazolyl, 3-, 4- or 5-pyrazolyl, 2-, 4- or 5-oxazolyl, 3-, 4- or 5-isoxazolyl, 2-, 4- or 5-thiazolyl, 3-, 4- or 5-isothiazolyl, 2-, 3- or 4-pyridyl, 2-, 4-, 5- or 6-pyrimidinyl, furthermore preferably 1,2,3-triazol-1-, -4- or -5-yl, 1,2,4-triazol-1-, -4- or -5-yl, 1- or 5-tetrazolyl, 1,2,3-oxadiazol-4- or -5-yl 1,2,4-oxadiazol-3- or -5-yl, 1,3,4-thiadiazol-2- or -5-yl, 1,2,4-thiadiazol-3- or -5-yl, 1,
- Heteroaryl-C 1 -C 6 -alkyl is now, analogously to aryl-C 1 -C 6 -alkyl, taken to mean for example pyridinylmethyl, pyridinylethyl, pyridinylpropyl, pyridinylbutyl, pyridinylpentyl, pyridinylhexyl, where furthermore the heterocyclic radicals described above may be linked to the alkylene chain in this way.
- R 1 ′ to R 4 ′ are, in particular, alkyl groups having 1 to 10 C atoms or hydroxyalkyl groups having 1 to 10 C atoms.
- Particularly suitable ionic liquids contain a tetraalkylammonium, tetraalkylphosphonium, 1,1-dialkylpyrrolidinium, 1-hydroxyalkyl-1-alkylpyrrolidinium, 1-hydroxyalkyl-3-alkylimidazolium or 1,3-bis(hydroxyalkyl)imidazolium cation, where the alkyl groups or the alkylene chain of the hydroxyalkyl group may each, independently of one another, have 1 to 10 C atoms.
- alkyl group having 1 to 10 C atoms is taken to mean, for example, methyl, ethyl, isopropyl, propyl, butyl, sec-butyl or tert-butyl, furthermore also pentyl, 1-, 2- or 3-methylbutyl, 1,1-, 1,2- or 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, heptyl, octyl, nonyl or decyl.
- the alkyl groups may also be partially or fully substituted by fluorine.
- Fluorinated alkyl groups are, for example, difluoromethyl, trifluoromethyl, pentafluoroethyl, pentafluoropropyl, heptafluoropropyl, heptafluorobutyl or nonafluorobutyl.
- a hydroxyalkyl group having 1 to 10 C atoms is taken to mean, for example, 1-hydroxymethyl, 2-hydroxyethyl, 3-hydroxyropyl, 4-hydroxybutyl, furthermore also 5-hydroxypentyl, 6-hydroxyhexyl, 7-hydroxyheptyl, 8-hydroxyoctyl, 9-hydroxynonyl or 10-hydroxydecyl.
- the alkylene chain of the hydroxyl group may also be partially or fully substituted by fluorine.
- Fluorinated hydroxyalkyl groups can be described, for example, by the sub-formulae —(CHF) n —OH or —(CF 2 ) n —OH, where n can denote 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.
- Suitable anions which, in combination with the cations according to the invention, satisfy the above-mentioned condition with respect to stability can be selected from the group PF 6 , BF 4 , alkylsulfate, perfluoroalkylsulfonate, perfluoroacetate, bis(fluorosulfonyl)imide, bis(perfluoroalkylsulfonyl)imide, tris(perfluoroalkyl)trifluorophosphate, bis(perfluoroalkyl)tetrafluorophosphate, tris(perfluoroalkylsulfonyl)methide or perfluoroalkylborate.
- perfluoroalkyl group means that all H atoms of the corresponding alkyl group have been replaced by F atoms.
- the alkyl or perfluoroalkyl groups in the anions indicated preferably each, independently of one another, have 1 to 10 C atoms, particularly preferably 1, 2, 3 or 4 C atoms.
- Anions which are suitable in accordance with the invention can be selected, from the group trifluoromethylsulfonate, pentafluoroethylsulfonate, heptafluoropropylsulfonate, nonafluorobutylsulfonate, bis(fluorosulfonyl)imide, perfluoroacetate, bis(trifluoromethylsulfonyl)imide, bis(pentafluoroethylsulfonyl)imide, bis(heptafluoropropylsulfonyl)imide, bis(nonafluorobutylsulfonyl)imide, tris(trifluoromethylsulfonyl)methide, tris(pentafluoroethylsulfonyl)methide, tris(heptafluoropropylsulfonyl)methide, tris(nonafluorobuty
- perfluoroalkyl groups can denote, independently of one another, different perfluoroalkyl groups.
- the above-mentioned definition therefore also covers, for example, mixed anions, such as trifluoromethylsulfonyl-pentafluoroethylsulfonylimide, bis(trifluoromethyl)sulfonyl-pentafluoroethylsulfonylmethide.
- the anions are particularly preferably selected from the group trifluoromethanesulfonate, bis(trifluoromethylsulfonyl)imide or tris(pentafluoroethyl)trifluorophosphate.
- Suitable cations are, in particular, optionally linear or branched, tetramethylammonium, tetraethylammonium, tetrapropylammonium, tetrabutylammonium, tetrapentylammonium, tetrahexylammonium, tetraheptylammonium, tetraoctylammonium, tetranonylammonium, tetradecylammonium, trimethylalkylammonium, trimethyl(ethyl)ammonium, triethyl(methyl)ammonium, trihexylammonium, methyl(trioctyl)ammonium, tetramethylphosphonium, tetraethylphosphonium, tetrapropylphosphonium, tetrabutylphosphonium, tetrapentylphosphonium, tetrahexylphosphonium,
- Particularly suitable cations are tetramethylammonium, trimethylalkylammonium, where the alkyl group can have 1 to 10 C atoms, in particular trihexyltetradecylphosphonium, triisobutyl(methyl)phosphonium, tributyl(ethyl)phosphonium, tributyl(methyl)phosphonium, in addition preferably 1-butyl-1-methylpyrrolidinium, 1-butyl-1-ethylpyrrolidinium, 1-hexyl-1-methylpyrrolidinium, 1-methyl-1-octylpyrrolidinium or 1-(2-hydroxyethyl)-3-methylimidazolium, very particularly suitable cations are 1-butyl-1-methylpyrrolidinium, 1-hexyl-1-methylpyrrolidinium, 1-methyl-1-octylpyrrolidinium or 1-(2-hydroxyethyl)-3-methyl-imidazolium.
- selenium ions are dissolved in a suitable ionic liquid, as described above.
- Suitable selenium salts are, for example, selenium tetrahalides, for example selenium tetrachloride or selenium tetrabromide, but also selenium dioxide. In principle, any selenium salt which facilitates selenium deposition under the said conditions is suitable.
- the ion concentration in the ionic liquid for the deposition of metal is preferably 10 ⁇ 5 to 10 mol/l.
- An ion concentration of 10 ⁇ 3 to 10 ⁇ 1 mol/l is preferably used.
- the deposition according to the invention is carried out in a protective-gas atmosphere, for example under argon, where the oxygen and water content and in particular the water content should be below 1 ppm.
- the deposition is carried out in a 3-electrode cell, as known to the person skilled in the art (for example from A. J. Bard, L. R. Faulkner, Electrochemical Methods, Wiley).
- platinum or selenium electrodes are preferably used as counter- and reference electrodes.
- all metals or carbon can be employed as electrode materials so long as the products formed at the counterelectrode do not interfere with the processes at the working electrode, i.e. so long as the electrode materials are not deposited together with selenium under the experimental conditions.
- the choice of suitable materials is made within the expert knowledge of the person skilled in the art.
- the process according to the invention is preferably carried out potentiostatically, at electrode potentials between 0 and ⁇ 2000 mV and at temperatures between 10° C. and 230° C., preferably between 100° C. to 150° C.
- the process according to the invention can also be carried out by means of pulsed techniques, as are known to the person skilled in the art, for example as described in J.-C. Puippe, F. Leaman, Pulse-Plating: Elektrolytician Metallabscheidung mit Pulsstrom [Pulse Plating: Electrolytic Deposition of Metal by Means of a Pulsed Current], Eugen G. Leuze Verlag, 1990.
- the process according to the invention enables grey selenium to be deposited in any desired layer thicknesses, for example between 200 ⁇ m and 300 ⁇ m, in continuous layers made up of micro- or nanocrystals.
- the desired layer thickness is controlled via the electrode potential and the charge that has flowed as well as the electrochemical parameters.
- the layer thickness can be set via the current and time.
- FIG. 1 shows a cyclic voltammogram of an approximately 0.1 molar solution of SeCl 4 in 1-butyl-1-methylpyrrolid inium bis(trifluoromethylsulfonyl)imide (BMP Tf 2 N) at room temperature on Au(111).
- a first reduction peak occurs at ⁇ 1 V vs. Pt quasi-reference and a second occurs at ⁇ 1.75 V.
- An oxidation process is evident at +0.5 volt, where the ratio of the anodic to the cathodic currents that have flowed is significantly less than 1.
- FIG. 3 shows the morphology of selenium deposits which have been deposited from SeCl 4 in BMP Tf2N. at 150° C.
- XRD X-ray diffraction, cobalt K alpha as X-ray
- a wide variety of substrates which can be employed as cathode are possible for the electrochemical deposition of selenium according to the invention.
- the geometry of the substrates is freely selectable and is not subject to any restriction.
- Suitable substrates can be selected, for example, from all categories, for example non-metals, semi-metals, metals, metal alloys, conductive or metallized ceramics or conductive or metallized plastics are possible.
- a preferred non-metal is, for example, graphite.
- a preferred semi-metal is, for example, silicon.
- Preferred metals are, for example, gold, platinum, copper, iron, cobalt, nickel or molybdenum.
- Preferred metal alloys are, for example, a very wide variety of steels or nickel alloys.
- Suitable substrates may also already consist, for example, of a plurality of layers to which a further layer of selenium is applied as interlayer or final layer by the process according to the invention.
- the list of substrates should therefore in no way be regarded as limiting. The person skilled in the art in the respective area of application will be able to select the suitable substrate without further information.
- the ionic liquid can be washed out using organic solvents.
- organic solvents are, for example, toluene, benzene, methylene chloride, acetonitrile, acetone, methanol, ethanol or isopropanol.
- selenium tetrachloride this can also be removed, for example, from the ionic liquid by heating under reduced pressure by distillation.
- the present invention likewise relates to substrates which are coated using the process according to the invention.
- the present invention furthermore relates to the use of ionic liquids for the deposition, preferably for the electrochemical deposition, of grey selenium on a substrate.
- a solution of SeCl 4 in the ionic liquid 1-butyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide is prepared and transferred into the 3-electrode measurement cell at room temperature under a protective-gas atmosphere.
- a typical 3-electrode measurement cell was used, as described, for example, in A. J. Bard and L. R. Faulkner, Electrochemical Methods, Wiley.
- the 3-electrode measurement cell has a gold electrode as working electrode (cathode), and platinum wires serve as quasi-reference and counter-electrode.
- the electrode potential is set to ⁇ 1500 mV vs. platinum quasi-reference.
- the deposition of selenium begins at ⁇ 1000 mV.
- a 0.25 molar solution of SeBr 4 in the ionic liquid 1-butyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide is prepared analogously to Example 1 and transferred into the 3-electrode measurement cell at room temperature under a protective-gas atmosphere.
- a typical 3-electrode measurement cell was used, as described, for example, in A. J. Bard and L. R. Faulkner, Electrochemical Methods, Wiley.
- the 3-electrode measurement cell has a platinum electrode as working electrode (cathode), and platinum wires serve as quasi-reference and counterelectrode.
- the electrode potential is set to ⁇ 1500 mV vs. platinum quasi-reference.
- the deposition of selenium begins at ⁇ 1000 mV.
- a 0.25 molar solution of SeBr 4 in the ionic liquid 1-butyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide is prepared analogously to Example 1 and transferred into the 3-electrode measurement cell at room temperature under a protective-gas atmosphere.
- a typical 3-electrode measurement cell was used, as described, for example, in A. J. Bard and L. R. Faulkner, Electrochemical Methods, Wiley.
- the 3-electrode measurement cell has an indium electrode as working electrode (cathode), and platinum wires serve as quasi-reference and counterelectrode.
- the electrode potential is set to ⁇ 1500 mV vs. platinum quasi-reference.
- the deposition of selenium begins at ⁇ 1000 mV.
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Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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DE102005046908.6 | 2005-09-30 | ||
DE102005046908A DE102005046908A1 (de) | 2005-09-30 | 2005-09-30 | Elektrochemische Abscheidung von Selen in ionischen Flüssigkeiten |
PCT/EP2006/008631 WO2007039035A1 (de) | 2005-09-30 | 2006-09-05 | Elektrochemische abscheidung von selen in ionischen flüssigkeiten |
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US12/088,130 Abandoned US20080210566A1 (en) | 2005-09-30 | 2006-09-05 | Electrochemical Deposition of Selenium in Ionic Liquids |
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US (1) | US20080210566A1 (de) |
EP (1) | EP1951934B1 (de) |
JP (1) | JP2009510261A (de) |
AT (1) | ATE440157T1 (de) |
DE (2) | DE102005046908A1 (de) |
TW (1) | TW200728516A (de) |
WO (1) | WO2007039035A1 (de) |
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WO2013173006A1 (en) * | 2012-05-14 | 2013-11-21 | United Technologies Corporation | Method for making metal plated gas turbine engine components |
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DE102009055828A1 (de) | 2008-12-19 | 2010-07-01 | Merck Patent Gmbh | Verfahren zur Herstellung metallbeschichteter Partikel |
GB2473285A (en) * | 2009-09-08 | 2011-03-09 | Astron Advanced Materials Ltd | Low temperature joining process |
DE102011080230A1 (de) | 2011-08-01 | 2013-02-07 | Helmholtz-Zentrum Dresden - Rossendorf E.V. | Extraktion von Edelmetall(ionen) mittels ionischer Flüssigkeiten |
WO2017099189A1 (ja) * | 2015-12-09 | 2017-06-15 | 学校法人 慶應義塾 | イオン液体を用いた放射性廃棄物からの長寿命核分裂生成物の分離および回収方法 |
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- 2006-09-05 AT AT06791833T patent/ATE440157T1/de active
- 2006-09-05 EP EP06791833A patent/EP1951934B1/de not_active Not-in-force
- 2006-09-05 JP JP2008532621A patent/JP2009510261A/ja active Pending
- 2006-09-05 WO PCT/EP2006/008631 patent/WO2007039035A1/de active Application Filing
- 2006-09-05 DE DE502006004616T patent/DE502006004616D1/de active Active
- 2006-09-05 US US12/088,130 patent/US20080210566A1/en not_active Abandoned
- 2006-09-29 TW TW095136252A patent/TW200728516A/zh unknown
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20110086272A1 (en) * | 2009-10-13 | 2011-04-14 | Kepler Keith D | Li-ion battery and its preparation method |
WO2013173006A1 (en) * | 2012-05-14 | 2013-11-21 | United Technologies Corporation | Method for making metal plated gas turbine engine components |
CN103122471A (zh) * | 2013-03-01 | 2013-05-29 | 沈阳师范大学 | 一种无氰镀铟的电镀液 |
Also Published As
Publication number | Publication date |
---|---|
DE102005046908A1 (de) | 2007-04-05 |
EP1951934B1 (de) | 2009-08-19 |
ATE440157T1 (de) | 2009-09-15 |
WO2007039035A1 (de) | 2007-04-12 |
JP2009510261A (ja) | 2009-03-12 |
DE502006004616D1 (de) | 2009-10-01 |
EP1951934A1 (de) | 2008-08-06 |
TW200728516A (en) | 2007-08-01 |
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