WO2010117204A2 - Production method for a metal nanostructure using an ionic liquid - Google Patents
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- WO2010117204A2 WO2010117204A2 PCT/KR2010/002127 KR2010002127W WO2010117204A2 WO 2010117204 A2 WO2010117204 A2 WO 2010117204A2 KR 2010002127 W KR2010002127 W KR 2010002127W WO 2010117204 A2 WO2010117204 A2 WO 2010117204A2
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82B—NANOSTRUCTURES FORMED BY MANIPULATION OF INDIVIDUAL ATOMS, MOLECULES, OR LIMITED COLLECTIONS OF ATOMS OR MOLECULES AS DISCRETE UNITS; MANUFACTURE OR TREATMENT THEREOF
- B82B1/00—Nanostructures formed by manipulation of individual atoms or molecules, or limited collections of atoms or molecules as discrete units
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B22—CASTING; POWDER METALLURGY
- B22F—WORKING METALLIC POWDER; MANUFACTURE OF ARTICLES FROM METALLIC POWDER; MAKING METALLIC POWDER; APPARATUS OR DEVICES SPECIALLY ADAPTED FOR METALLIC POWDER
- B22F9/00—Making metallic powder or suspensions thereof
- B22F9/16—Making metallic powder or suspensions thereof using chemical processes
- B22F9/18—Making metallic powder or suspensions thereof using chemical processes with reduction of metal compounds
- B22F9/24—Making metallic powder or suspensions thereof using chemical processes with reduction of metal compounds starting from liquid metal compounds, e.g. solutions
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82B—NANOSTRUCTURES FORMED BY MANIPULATION OF INDIVIDUAL ATOMS, MOLECULES, OR LIMITED COLLECTIONS OF ATOMS OR MOLECULES AS DISCRETE UNITS; MANUFACTURE OR TREATMENT THEREOF
- B82B3/00—Manufacture or treatment of nanostructures by manipulation of individual atoms or molecules, or limited collections of atoms or molecules as discrete units
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B22—CASTING; POWDER METALLURGY
- B22F—WORKING METALLIC POWDER; MANUFACTURE OF ARTICLES FROM METALLIC POWDER; MAKING METALLIC POWDER; APPARATUS OR DEVICES SPECIALLY ADAPTED FOR METALLIC POWDER
- B22F9/00—Making metallic powder or suspensions thereof
- B22F9/16—Making metallic powder or suspensions thereof using chemical processes
- B22F9/18—Making metallic powder or suspensions thereof using chemical processes with reduction of metal compounds
- B22F9/24—Making metallic powder or suspensions thereof using chemical processes with reduction of metal compounds starting from liquid metal compounds, e.g. solutions
- B22F2009/245—Reduction reaction in an Ionic Liquid [IL]
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B22—CASTING; POWDER METALLURGY
- B22F—WORKING METALLIC POWDER; MANUFACTURE OF ARTICLES FROM METALLIC POWDER; MAKING METALLIC POWDER; APPARATUS OR DEVICES SPECIALLY ADAPTED FOR METALLIC POWDER
- B22F2999/00—Aspects linked to processes or compositions used in powder metallurgy
Definitions
- the present invention relates to a method for producing a nano-sized metal nanostructure, and more specifically, by using an ionic liquid in a polyol reduction reaction using a metal salt as a precursor, various forms such as cubic or octahedral particles and nanowires.
- the present invention relates to a method for uniformly preparing a metal nanostructure.
- metal nanoparticles for various fields such as flat panel displays, touch panels and solar cells. Since these metal nanoparticles can be applied to various fields such as transparent electrodes or conductive inks, there is a need for an invention of mass production of these metal nanoparticles. At this time, since the shape of the metal nanoparticles is an important factor influencing the characteristics of the electrical conductivity and the like, an invention of a technology capable of freely controlling the shape of the metal nanoparticles is required.
- a technique for producing a metal structure in the form of a wire has been reported.
- the technique is called a polyol reduction method, and this method has an advantage that it is relatively easy to prepare a solution-shaped metal nanostructure.
- the metal nanostructures prepared by the above-described methods are often wire-shaped, but the structure having the shape of other nanoparticles as well as the wire is often mixed, and the shape of the nano-structure is reproducible depending on the reaction conditions. There is a disadvantage of being difficult.
- the present invention is a method for producing a metal nanostructure of various shapes by mixing and reacting an ionic liquid, a metal salt and a reducing solvent.
- the present invention is characterized in that the shape structure of the metal nanostructure is determined by the chemical bonding structure of the cation and anion constituting the ionic liquid by mixing and reacting the ionic liquid, the metal salt and the reducing solvent.
- the present invention is a method for producing a metal nanostructure by mixing and reacting an ionic liquid, a metal salt and a reducing solvent, wherein the metal nanostructure by the ionic liquid various structures including a one-dimensional, two-dimensional or three-dimensional shape Characterized in that to have.
- a method of changing the shape of the metal nanoparticles by using an ionic liquid in the polyol reduction reaction of the precursor of the metal salt and changing the anion component of the ionic liquid.
- the present invention is to prepare a metal particle through a polyol reduction reaction by mixing and reacting an ionic liquid, a metal salt and a reducing solvent, to prepare metal nanoparticles of different shapes by varying the type of anion of the ionic liquid. It is done.
- the metal salt may be AgNO 3 , Ag (CH 3 COO) 2 , AgClO 4 , Au (ClO 4 ) 3 , PdCl 2 , NaPdCl 4 , PtCl 2, SnCl 4 , HAuCl 4 , FeCl 2 , FeCl 3 , Fe (CH 3 COO ) 2 , CoCl 2 , K 4 Fe (CN) 6 , K 4 Co (CN) 6 , K 4 Mn (CN) 6, K 2 CO 3, including most metal cations and organic or inorganic anions, Most metal salts can be used without being limited to metal elements.
- the metal salt is converted into the corresponding metal nanoparticles such as silver, gold, palladium, tin, iron, and cobalt through a reduction reaction.
- the reducing solvent is a polar solvent capable of dissolving a metal salt, and refers to a solvent such as diol, polyol, or glycol having at least two hydroxyl groups in a molecule. Specific examples thereof include ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, glycerin, glycerol, polyethylene glycol, polypropylene glycol, and the like.
- the polyol reducing solvent serves to induce a reduction reaction of the metal salt to generate metal elements.
- the ionic liquid is a compound composed of an organic cation and an organic or inorganic anion, and is characterized in that it is an imidazolium ionic liquid of Formula 1a and / or a pyridinium ionic liquid of Formula 1b.
- R 1 and R 2 are the same or different, and represent hydrogen or a hydrocarbon group having 1 to 16 carbon atoms, and may include a heteroatom.
- X ⁇ represents an anion of an ionic liquid.
- R 3 and R 4 are the same or different, and represent hydrogen or a hydrocarbon group having 1 to 16 carbon atoms, and may include heteroatoms.
- X ⁇ represents an anion of an ionic liquid.
- Specific examples of the cation of the imidazolium ionic liquid represented by the formula (1a) include 1,3-dimethylimidazolium, 1,3-diethylimidazolium, 1-ethyl-3-methylimidazolium , 1-butyl-3-methylimidazolium, 1-hexyl-3-methylimidazolium, 1-octyl-3-methylimidazolium, 1-decyl-3-methylimidazolium, 1-dodecyl- 3-methylimidazolium, 1-tetradecyl-3-methylimidazolium, and the like.
- Examples of the pyridinium-based ionic liquid cation represented by Formula 1b include 1-methylpyridinium, 1-ethylpyridinium, 1-butylpyridinium, 1-ethyl-3-methylpyridinium, 1-butyl-3-methylpyridinium, 1-hexyl-3-methylpyridinium, 1-butyl-3,4-dimethylpyridinium .
- the ionic liquid cation of the present invention includes not only the ionic liquid of the monomolecular form represented by the formula (1a) or the formula (1b) but also the ionic liquid of the polymer form, for example, poly (1-vinyl-3-alkylimide). Jolium), poly (1-vinyl-pyridinium), poly (1-vinyl-alkylpyridinium), poly (1-allyl-3-alkylimidazolium), poly (1- (meth) acryloyloxy- 3-alkylimidazolium), and the like, and are not limited to any particular compound.
- the monomolecular or ionic liquid in a polymer form having an organic or inorganic anion for example, Br -, Cl -, I - , BF 4 -, PF 6 -, ClO 4 -, NO 3 -, AlCl 4 -, Al 2 Cl 7 -, AsF 6 -, SbF 6 -, CH 3 COO -, CF 3 COO -, CH 3 SO 3 -, C 2 H 5 SO 3 -, CH 3 SO 4 -, C 2 H 5 SO 4 -, CF 3 SO 3 -, (CF 3 SO 2) 2 N -, (CF 3 SO 2) 3 C -, (CF 3 CF 2 SO 2) 2 N -, C 4 F 9 SO 3 -, C 3 F 7 COO -, (CF 3 SO 2) (CF 3 CO) N - and the like, and is not limited to any particular compound.
- an organic or inorganic anion for example, Br -, Cl -, I - , BF 4 -
- the ionic liquid in the form of a single molecule or a polymer can be configured with various physical and chemical properties depending on the combination of cations and anions.
- the ionic liquid has a high compatibility with metal salts and reducing solvents.
- the ionic liquid serves to help the metal element to grow one-dimensional, two-dimensional, or three-dimensional by chemically interacting with the metal ion or the metal element when the metal salt is converted into the metal element by the polyol reduction reaction. Finally, metal particles having a uniform shape are produced.
- the anion component of the ionic liquid determines the shape of the finally prepared metal nanoparticles, for example, an ionic having an anion of a sulfur compound such as alkyl sulfate (RSO 4 ⁇ ) or alkyl sulfonate (RSO 3 ⁇ ).
- metal nanoparticles having different shapes can be selectively produced.
- the final shape of the nanostructures is that the growth direction of the metal nanoparticles is changed by the interaction between the metal nanoparticles and the ionic liquid in the initial stage of the reaction, so the anion of the ionic liquid plays an important role in this step. . That is, at the beginning of the reaction, metal salts are first formed by the reducing solvent, and metal nanoparticles are first formed, and the metal nanoparticles interact with the anions (Cl-, Br-, CH3SO4-) of the ionic liquid to help growth in a certain direction. Thus, the metal nanostructures of various shapes can be manufactured.
- a specific method of manufacturing a metal nanostructure having a nanowire shape is as follows. First, the ionic liquid consisting of the metal salt, the reducing solvent and the sulfide anion is mixed at an appropriate ratio and stirred at room temperature for a certain time. When uniform mixing is achieved, the metal nanowires are manufactured by continuing the reaction by raising the reaction temperature of the mixture to 150-200 degrees Celsius. The metal nanowires thus prepared have almost no nanoparticle shape, and have a nanowire shape having an average diameter of 0.01 to 0.1 micron and an average length of 5 to 100 microns.
- the concentration of the metal salt is 1 mol or more, the content of the metal salt is so high that the resulting metal particles stick to each other or the particle size is disadvantageous, or if the content of the ionic liquid is 1 mol or more, the total solution Too high a viscosity of the metal nanowires synthesis is difficult and rather disadvantageous.
- R 5 , R 6 , R 7 and R 8 are the same or different, represent a hydrocarbon group having 1 to 20 carbon atoms, and may include a hetero atom.
- Y ⁇ represents an organic or inorganic anion.
- R represents a hydrocarbon group in the form of a single molecule or a polymer, and may include a heteroatom.
- Y ⁇ represents an organic or inorganic anion.
- Examples of the nitrogen compound represented by Formula 2a include tetrabutylammonium chloride, cetyltrimethylammonium bromide, tetrabutylphosphonium chloride and the like.
- Examples of the sulfur compound represented by Formula 2b include sodium dodecyl sulfate, dodecylbenzenesulfonate, Polystyrenesulfonate, poly (sodium-4-styrenesulfonate), and the like.
- metal nanostructures of various shapes can be prepared by mixing and reacting ionic liquids, metal salts and reducing solvents.
- metal nanoparticles having different shapes can be selectively and reproducibly produced.
- Example 4 A metal nanostructure was prepared in the same manner as in Example 1, except that 1-ethyl-3-methylpyridinium methyl sulfate was used as the ionic liquid. The solution was filtered through a filter having a pore size of 1 micron, and observed with an electron scanning microscope to confirm that nanowires were formed. The diameter of the nanowires was about 320 nanometers and the length was observed to be about 5 microns.
- Example 5 was a metal nanostructure was prepared in the same manner as in Example 1, except that 1-butyl-3-methylimidazolium chloride was used as the ionic liquid. Finally, the resulting reaction solvent was filtered through a 0.2 micron Teflon filter, and then observed with an electron scanning microscope, and as shown in FIG. 2, silver nanoparticles having a cube shape of about 400 nanometers were formed.
- Example 6 A metal structure was prepared in the same manner as in Example 1 except that 1-butyl-3-methylimidazolium bromide was used as the ionic liquid. Finally, the resultant reaction solvent was filtered through a 1 micron filter, and then observed with an electron scanning microscope to confirm that silver particles having an octahedral shape of about 5 microns were formed as shown in FIG. 3.
- the metal nanostructures prepared according to the present invention can be used in various industrial fields such as flat panel displays, touch panels, and solar cells.
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Abstract
Description
Claims (12)
- 이온성 액체, 금속염 및 환원용매를 혼합, 반응시킴으로써 다양한 형상의 금속 나노구조체를 제조하는 금속 나노구조체 제조방법.Metal nanostructure manufacturing method for producing metal nanostructures of various shapes by mixing and reacting an ionic liquid, a metal salt and a reducing solvent.
- 제1항에 있어서, 상기 이온성 액체를 구성하는 양이온 및 음이온의 화학적 결합 구조에 의해 금속 나노구조체의 형상 구조가 결정되는 것을 특징으로 하는 금속 나노구조체 제조방법.The method of claim 1, wherein the shape structure of the metal nanostructure is determined by the chemical bonding structure of the cation and anion constituting the ionic liquid.
- 제1항 또는 제2항에 있어서, 상기 이온성 액체를 구성하는 음이온 성분이 알킬설페이트(RSO4 -)나 알킬설포네이트(RSO3 -)를 포함하는 황화합물의 음이온을 가진 이온성 액체를 사용하여 나노와이어 형태와 같은 1차원 형상의 구조를, 할라이드(Halide)계 음이온을 가진 이온성 액체를 사용하여 3차원 형상의 구조를, 염소 음이온 (Cl-)의 경우 큐브형태 구조를, 그리고 브롬 음이온 (Br-)의 경우 팔면체의 입자 형상의 구조를, 가지도록 하는 것을 특징으로 하는 금속 나노구조체 제조방법.The method of claim 1 or claim 2, wherein the anion component constituting the ionic liquid alkyl sulfate with an ionic liquid having an anion of the sulfur compounds comprising the (RSO 4 - -) or alkyl sulfonate (RSO 3) One-dimensional structure such as nanowire form, three-dimensional structure using ionic liquid with halide-based anion, cube-shaped structure for chlorine anion (Cl − ), and bromine anion ( Br - manufacturing method is characterized in that so as to have the structure of the particle shape of octahedral metal nanostructure case).
- 제1항 내지 제3항 중 어느 한 항에 있어서, 상기 이온성 액체는 유기 양이온 및 유기 또는 무기 음이온으로 구성된 화합물로서 단분자 형태이거나 또는 고분자 형태임을 특징으로 하는 금속 나노구조체 제조방법.The method according to any one of claims 1 to 3, wherein the ionic liquid is composed of an organic cation and an organic or inorganic anion and is in the form of a single molecule or a polymer.
- 제1항 내지 제4항 중 어느 한 항에 있어서, 상기 이온성 액체의 양이온으로는 하기 화학식 1a의 이미다졸리움계 양이온, 하기 화학식 1b의 피리디늄계 양이온을 포함하는 것으로서 단분자 형태 이거나 또는 고분자 형태임을 특징으로 하는 금속 나노구조체 제조방법.The method according to any one of claims 1 to 4, wherein the cation of the ionic liquid includes an imidazolium-based cation of Formula 1a and a pyridinium-based cation of Formula 1b, and is in a monomolecular form or a polymer. Metal nanostructure manufacturing method characterized in that the form.<화학식 1a><Formula 1a>상기 화학식 1a에서 R1 및 R2 는 동일하거나 또는 상이하며, 수소 또는 탄소수 1 내지 16의 탄화수소기를 나타내고, 헤테로원자를 포함할 수도 있다. 또한 X-는 이온성 액체의 음이온을 나타낸다. In Formula 1a, R 1 and R 2 are the same or different, and represent hydrogen or a hydrocarbon group having 1 to 16 carbon atoms, and may include a heteroatom. And X − represents an anion of an ionic liquid.<화학식 1b><Formula 1b>상기 화학식 1b에서 R3 및 R4 는 동일하거나 또는 상이하며, 수소 또는 탄소수 1 내지 16의 탄화수소기를 나타내고, 헤테로원자를 포함할 수도 있다. 또한 X-는 이온성 액체의 음이온을 나타낸다.In Formula 1b, R 3 and R 4 are the same or different, and represent hydrogen or a hydrocarbon group having 1 to 16 carbon atoms, and may include heteroatoms. And X − represents an anion of an ionic liquid.
- 제1항 내지 제5항 중 어느 한 항에 있어서, 상기 이온성 액체의 음이온으로는 The anion of the ionic liquid according to any one of claims 1 to 5, whereinBr-, Cl-, I-, BF4 -, PF6 -, ClO4 -, NO3 -, AlCl4 -, Al2Cl7 -, AsF6 -, SbF6 -, CH3COO-, CF3COO-, CH3SO3 -, C2H5SO3 -, CH3SO4 -, C2H5SO4 -, CF3SO3 -, (CF3SO2)2N-, (CF3SO2)3C-, (CF3CF2SO2)2N-, C4F9SO3 -, C3F7COO-, (CF3SO2)(CF3CO)N- 중 어느 하나를 사용하는 것을 특징으로 하는 금속 나노구조체 제조방법. Br -, Cl -, I - , BF 4 -, PF 6 -, ClO 4 -, NO 3 -, AlCl 4 -, Al 2 Cl 7 -, AsF 6 -, SbF 6 -, CH 3 COO -, CF 3 COO -, CH 3 SO 3 - , C 2 H 5 SO 3 -, CH 3 SO 4 -, C 2 H 5 SO 4 -, CF 3 SO 3 -, (CF 3 SO 2) 2 N -, (CF 3 SO 2) 3 C -, ( CF 3 CF 2 SO 2) 2 N -, C 4 F 9 SO 3 -, C 3 F 7 COO -, (CF 3 SO 2) (CF 3 CO) N - either the Metal nanostructures manufacturing method characterized in that using.
- 제1항 내지 제6항 중 어느 한 항에 있어서, 상기 금속염은 금속 양이온 및 유기 또는 무기 음이온으로 이루어진 것으로서 AgNO3, Ag(CH3COO)2, AgClO4, Au(ClO4)3, PdCl2, NaPdCl4, PtCl2, SnCl4, HAuCl4, FeCl2, FeCl3, Fe(CH3COO)2, CoCl2, K4Fe(CN)6, K4Co(CN)6, K4Mn(CN)6, K2CO3 중 어느 하나를 사용하는 것을 특징으로 하는 금속 나노구조체 제조방법.The method according to any one of claims 1 to 6, wherein the metal salt is composed of a metal cation and an organic or inorganic anion, AgNO 3 , Ag (CH 3 COO) 2 , AgClO 4 , Au (ClO 4 ) 3 , PdCl 2 , NaPdCl 4 , PtCl 2, SnCl 4 , HAuCl 4 , FeCl 2 , FeCl 3 , Fe (CH 3 COO) 2 , CoCl 2 , K 4 Fe (CN) 6 , K 4 Co (CN) 6 , K 4 Mn ( CN) Method for producing a metal nanostructure, characterized in that using any one of 6, K 2 CO 3 .
- 제1항 내지 제7항 중 어느 한 항 에 있어서, 환원용매는 분자내에 히드록시기를 적어도 2개 이상 가지는 다이올, 폴리올 또는 글리콜등의 용매로서 에틸렌 글리콜, 1,2-프로필렌글리콜, 1,3-프로필렌글리콜, 글리세린, 글리세롤, 폴리에틸렌글리콜, 폴리프로필렌글리콜 중 어느 하나를 사용하는 것을 특징으로 하는 금속 나노구조체 제조방법.8. The reducing solvent according to any one of claims 1 to 7, wherein the reducing solvent is a solvent such as diol, polyol or glycol having at least two or more hydroxyl groups in the molecule, and ethylene glycol, 1,2-propylene glycol, 1,3- Method for producing a metal nanostructure, characterized in that any one of propylene glycol, glycerin, glycerol, polyethylene glycol, polypropylene glycol.
- 제1항 내지 제8항 중 어느 한 항 에 있어서, 이온성 액체, 금속염 및 환원 용매의 혼합비율은 환원용매에 대해 금속염 0.01 내지 1 몰농도 및 이온성 액체 (고분자 형태의 이온성 액체인 경우에는 반복단위 기준으로) 0.001 내지 1 몰농도을 특징으로 하는 금속 나노구조체 제조방법.The method according to any one of claims 1 to 8, wherein the mixing ratio of the ionic liquid, the metal salt and the reducing solvent is 0.01 to 1 molar concentration of the metal salt and the ionic liquid (in the case of the ionic liquid in the form of polymer) Method of manufacturing a metal nanostructure, characterized in that the molar concentration of 0.001 to 1).
- 제1항 내지 제9항 중 어느 한 항에 있어서, 이온성 액체, 금속염 및 환원용매 이외에 하기 화학식 2a의 질소화합물 및 화학식 2b의 황화합물을 추가로 포함하는 것을 특징으로 하는 금속 나노구조체 제조방법.10. The method of claim 1, further comprising a nitrogen compound of Formula 2a and a sulfur compound of Formula 2b in addition to an ionic liquid, a metal salt, and a reducing solvent.<화학식 2a><Formula 2a>여기서, R5, R6, R7 및 R8은 동일하거나 또는 상이하며, 탄소수 1 내지 20의 탄화수소기를 나타내고, 헤테로 원자를 포함할 수 도 있다. 또한 Y-는 유기 또는 무기 음이온을 나타낸다.Here, R 5 , R 6 , R 7 and R 8 are the same or different, represent a hydrocarbon group having 1 to 20 carbon atoms, and may include a hetero atom. And Y − represents an organic or inorganic anion.<화학식 2b> <Formula 2b>여기서, R은 단분자 또는 고분자형태의 탄화수소기를 나타내고, 헤테로원자를 포함할 수도 있다. 또한 Y-는 유기 또는 무기 음이온을 나타낸다.Here, R represents a hydrocarbon group in the form of a single molecule or a polymer, and may include a heteroatom. And Y − represents an organic or inorganic anion.
- 제10항에 있어서, 상기 질소화합물 및 황화합물의 농도가 금속염 100 중량부를 기준으로 0.1 내지 100 중량부임을 특징으로 하는 금속 나노구조체 제조방법.The method of claim 10, wherein the concentration of the nitrogen compound and the sulfur compound is 0.1 to 100 parts by weight based on 100 parts by weight of the metal salt.
- 제1항 내지 제11항의 방법을 이용하여 제조된 금속 나노구조체.Metal nanostructures prepared using the method of claim 1.
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CN201080014483.0A CN102369154B (en) | 2009-04-08 | 2010-04-07 | Production method for a metal nanostructure using an ionic liquid |
US13/263,350 US20120034129A1 (en) | 2009-04-08 | 2010-04-07 | Production method for a metal nanostructure using an ionic liquid |
JP2012504611A JP6041138B2 (en) | 2009-04-08 | 2010-04-07 | Method for producing metal nanostructure using ionic liquid |
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KR20090030599A KR101479788B1 (en) | 2009-04-08 | 2009-04-08 | Method for producing metal nano structures using ionic liquid |
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JP (1) | JP6041138B2 (en) |
KR (1) | KR101479788B1 (en) |
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CN103459622A (en) * | 2010-12-17 | 2013-12-18 | 南澳大利亚大学 | Extraction of gold |
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TW201100558A (en) | 2011-01-01 |
US20120034129A1 (en) | 2012-02-09 |
KR20100112049A (en) | 2010-10-18 |
JP2012523499A (en) | 2012-10-04 |
CN102369154A (en) | 2012-03-07 |
KR101479788B1 (en) | 2015-01-06 |
JP6041138B2 (en) | 2016-12-07 |
CN102369154B (en) | 2015-02-18 |
WO2010117204A3 (en) | 2011-01-20 |
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