WO2012169767A2 - Procédé de production de nanoparticules conductrices pouvant être dispersées dans l'eau - Google Patents

Procédé de production de nanoparticules conductrices pouvant être dispersées dans l'eau Download PDF

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Publication number
WO2012169767A2
WO2012169767A2 PCT/KR2012/004436 KR2012004436W WO2012169767A2 WO 2012169767 A2 WO2012169767 A2 WO 2012169767A2 KR 2012004436 W KR2012004436 W KR 2012004436W WO 2012169767 A2 WO2012169767 A2 WO 2012169767A2
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WO
WIPO (PCT)
Prior art keywords
conductive water
conductive
dispersible nanoparticles
emulsion
producing
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/KR2012/004436
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English (en)
Korean (ko)
Other versions
WO2012169767A3 (fr
Inventor
김중현
김병욱
이선종
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KOREA NTCHEM CO Ltd
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KOREA NTCHEM CO Ltd
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Priority to CN201280028262.8A priority Critical patent/CN103748032A/zh
Publication of WO2012169767A2 publication Critical patent/WO2012169767A2/fr
Publication of WO2012169767A3 publication Critical patent/WO2012169767A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
    • H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
    • H01B1/124—Intrinsically conductive polymers
    • H01B1/127—Intrinsically conductive polymers comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
    • 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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/14—Conductive material dispersed in non-conductive inorganic material
    • H01B1/18—Conductive material dispersed in non-conductive inorganic material the conductive material comprising carbon-silicon compounds, carbon or silicon
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y40/00—Manufacture or treatment of nanostructures

Definitions

  • the present invention relates to a method for producing conductive water-dispersible nanoparticles having a high degree of polymerization by a conventional method, and the conductive polymer produced has excellent processability and high electrical conductivity.
  • the conductive polymer is a material that can simultaneously possess the electrical, magnetic, and optical properties of the metal, the physical properties of the general polymer, and the ease of processing, and is light, flexible, and can freely control the electrical conductivity and the electronic state. Therefore, the scope of application to existing metal replacement and electronic materials, etc. is very wide.
  • Common uses of conductive polymers are as follows. 1) antistatic agent; The coating prevents the generation of static electricity generated on the surface of plastics and polymers. 2) condenser; Use as an electrolyte substitute. 3) printed circuit board (PCB) substrate coating; As a substitute for conventional metal plating, environmental pollution can be minimized. 4) organic electroluminescence (EL) devices; It is used as a hole injecting layer of an indium tin oxide (ITO) substrate.
  • ITO indium tin oxide
  • the conductive polymer has excellent electrical properties, but has a disadvantage in that the mechanical properties such as workability is slightly inferior to the conventional general polymer. That is, they have poor thermal stability, poor solvent resistance (especially base), and long-term limitations.
  • the conductive polymers may have electrical conductivity only in the doped state (p-doped), and do not have electrical conductivity when de-doped (or neutral, n-doped).
  • the role of dopant is important.
  • the polythiophene produced by the oxidative polymer reaction has electrical conductivity because the oxidant used in the manufacturing process plays a role of the dopant.
  • the polythiophene powder prepared in the organic solvent condition by the oxidizing polymer reaction is insoluble, and the doped polythiophene prepared under the aqueous solution is also present in the dispersed state in the aqueous solution by the used surfactant or the like. That is, polythiophene prepared by the oxidizing polymer method is insoluble in any solvent.
  • polypyrrole and polyfuran are not easily dissolved in organic solvents, so they are not easily processed, and the activity of molecules in the polymer backbone is limited, thereby affecting conductivity. Very unstable at
  • Korean Patent Application Nos. 10-2005-0093714 and 10-2008-0064545 describe methods for preparing polythiophene nanoparticles.
  • the present invention was derived to solve the above-mentioned problems, a high polymerization degree, the method of producing a conductive water-dispersible nanoparticles having a high processability and high electrical conductivity of the conductive polymer to be produced and the conductive water-dispersible nanoparticles prepared thereby It aims to provide.
  • the present invention to achieve the above object
  • thiophene, pyrrole or furan monomer in an aqueous solvent Compounds selected from the group consisting of HCl, HF, HBr and HI; Stabilizer; And mixing the first oxidant to prepare an emulsion.
  • step b) mixing the second oxidant into the emulsion of step a) and stirring to prepare conductive particles in an emulsion state;
  • It provides a method for producing a conductive water-dispersible nanoparticles comprising a.
  • the present invention also provides a conductive water-dispersible nanoparticles prepared by the above method.
  • the present invention provides an electronic material, optical material, toner or ink made of the conductive water-dispersible nanoparticles.
  • the conductive water dispersible nanoparticles prepared according to the method of the present invention exhibit excellent processability and high conductivity compared to conventionally prepared conductive nanoparticles.
  • a second oxidant such as a trace amount of iron salts and other oxidants and stabilizers (stabilizer) that can be oxidized again when the second oxidant is reduced.
  • Polythiophene, polypyrrole and polyfuran particles having excellent processability and conductivity can be prepared when the emulsion is granulated in the presence of a substance which simultaneously performs the composition of the acid atmosphere and the dopant function.
  • the present invention has been completed by focusing on the fact that the present invention exists.
  • thiophene, pyrrole or furan monomer in an aqueous solvent Compounds selected from the group consisting of HCl, HF, HBr and HI; Stabilizer; And mixing the first oxidant to prepare an emulsion.
  • step b) mixing the second oxidant into the emulsion of step a) and stirring to prepare conductive particles in an emulsion state;
  • the conductive water dispersible nanoparticles prepared in the present invention may be represented by the following Chemical Formula 1.
  • X represents sulfur, nitrogen, oxygen, phosphorus, silicon, or arsenic
  • R 1 and R 2 are each independently hydrogen, halogen, hydroxy, C1-C10 alkyl, alkoxy, carbonyl
  • 3 to 8 may be alkylene, alkenylene, alkenyloxy, alkenyldioxy, alkynyloxy, alkynyldioxy in the membered alicyclic or aromatic ring structure, and in addition to hydrogen, carbon, oxygen atoms, nitrogen, sulfur And atoms such as phosphorus, selenium, and silicon.
  • the thiophene, pyrrole or furan monomer as the starting material is a starting material prepared from polythiophene, polypyrrole and polyfuran through a polymerization reaction, and any thiophene, pyrrole and furan commonly used in the art may be used. It may be used, for example, it may be represented by the following formula (2), preferably thiophene, pyrrole or furan substituted with an alkyl ethoxy, carboxyl sulfone group or at least one substituent selected from them.
  • the compound selected from the group consisting of HCl, HF, HBr and HI makes the reaction solution acid (pH 1-6) and at the same time acts as a dopant (dopant), especially HCl is preferred.
  • the conductive polymer can be produced significantly improved electrical conductivity and processability of the conductive water-dispersible nanoparticles prepared by the present invention compared to the conventional conductive polymer.
  • the amount of the compound such as HCl is preferably used in 1 to 100 mole ratio (mole ratio) of the monomer. In the case where the molar ratio is less than 1, the progress of the reaction is delayed, the yield is low, and the electrical conductivity of the reaction product is low. When the molar ratio is more than 100, the acid value of the product is high, which makes it difficult to neutralize and wash the production cost. This increase is somewhat problematic for commercial use.
  • the solvent used in the present invention is one selected from the group consisting of C 6 -C 20 aliphatic and aromatic hydrocarbons, halogen-containing hydrocarbons, ketones, ethers, C 2 -C 20 alcohols, sulfoxides, amides, and water or You may mix and use 2 or more.
  • C 6 -C 20 aliphatic and aromatic hydrocarbons are alkanes giant amphipods hexane, heptane, octane, nonane, decane, and alkylbenzene giant amphipods benzene, toluene, xylene, cumene (cumene), champignon ethylene (mesitylene), Phenol, cresol, and the like
  • halogen-containing hydrocarbons include carbon tetrachloride, chloroform, dichloromethane, dichloroethane, dibromoethane, trichloroethane, tribromoethane, and halobenzenes such as dichlorobenzene and chlorobenzene, and ketones include acetone.
  • ethers are diethyl ether, tetrahydro hulan (THF), dipropyl ether, dibutyl ether, methyl butyl ether , Diphenyl ether, dioxane, diglyme, diethylene glycol, ethylene glycol (EG), and C2-C20 alcohols and sulfoxides include dimethylsulfoxide (DMSO).
  • Amide series are N, N-dimethylformamide (NMF), N-methylacetamide (NMAA), N, N-dimethylacetamide (DMA), N-methylpropionamide (NMPA), N Methylpyrrolidinone (NMP).
  • the solvent is used in an amount of 1,000 to 3,000 parts by weight based on 100 parts by weight of the monomer, water having a temperature range of 0-180 °C and C 2 -C 20 alcohols, DMSO, DMF, NMP, ether, Polar solvents such as ethylene glycol and the like are suitable.
  • the stabilizer (Stabilizer) according to the present invention is to be mixed with the pyrrole and furan or derivatives thereof to impart the stability of the particles, any stabilizer (stabilizer) commonly used in the art to achieve this purpose.
  • the stabilizer may be polystyrene sulfonic acid [poly (4-styrene sulfonic acid)], polyacrylic acid [poly (acrylic acid)], polymethacrylic acid [poly (methacrylic acid)] polymaleic acid [poly (maleic) acid)], poly (vinyl sulfonic acid), dodecyl trimethyl ammonium bromide, cetyl trimethlammonium bromide, dodecyl dimethyl ammonium bromide didodcyl dimethl ammonium bromide], Span 80], Tween 20 [Tween 20, polyoxyethylene (20) sorbitanmonolaurate], Perfluorooctnoic acid, Cety
  • the amount of the stabilizer used is preferably 0.01 to 2,000 parts by weight based on 100 parts by weight of the monomer. If the content is less than 0.01 parts by weight, the micelle formation concentration does not function as a stabilizer, so it is not possible to induce the polymerization of the chain-type nanoparticles, and the aggregation of the particles occurs. The amount of c) may be so excessive that formation of the chained nanoparticles may be difficult.
  • the first oxidizing agent according to the present invention is to oxidize the reduced second oxidant when the second oxidant is reduced by oxidizing the thiophene, pyrrole or furan monomer, so that the second oxidant has an oxidizing power.
  • Any object can be used as long as the object can be achieved, but an oxidizing agent having a relatively higher oxidizing power than that of the second oxidizing agent is preferable, and preferably peroxides [H 2 O 2 , (NH 4 ) 2 S 2 O 8 , O 2 ] or oxygen acids [HMnO 4 , HNO 3 , HClO 4 ], halogens [F 2 , Cl 2 , Br 2 ] or mixtures thereof are preferably used.
  • the amount of the first oxidizing agent added is preferably 0.01 to 10 mole ratio of the monomer. If the content of the first oxidant is less than 0.01 molar ratio, the reaction for reducing the second oxidant may not occur well, and thus the degree of polymerization of the chain-type nanoparticles may be lowered. Can be.
  • the second oxidizing agent is for oxidizing the monomer, and any oxidizing agent capable of achieving this object may be used, but preferably, a metal oxide such as FeCl 3 , Fe (SO 4 ) 2.
  • Iron (III) complexes such as 6H 2 O, iron (II) complexes, or mixtures thereof may be used, and the amount of use thereof is preferably 0.001 to 5 mole ratio with respect to the monomers.
  • the amount of the second oxidant is less than 0.001 mole ratio of the monomer, the polymerization rate is very slow. If the amount of the second oxidant is more than 5 mole ratio, the rate of polymerization and the electrical conductivity are increased, but the physical properties of the produced conductive polymer are decreased.
  • the second oxidant may be directly incorporated into a mixture of starting materials for polymerization, for example, a monomer, a compound such as HCl, a stabilizer, a first oxidant, and a solvent, but preferably deionized water. (Deionized water, DI Water) and / or mixed in a mixture of the starting materials in a state dissolved in an organic solvent.
  • a monomer for example, a monomer, a compound such as HCl, a stabilizer, a first oxidant, and a solvent, but preferably deionized water. (Deionized water, DI Water) and / or mixed in a mixture of the starting materials in a state dissolved in an organic solvent.
  • DI Water DI Water
  • the reaction temperature of the polymer polymerization reaction is preferably 0-180 ° C., or the temperature at which the solvent is used, and is stirred for 6 to 24 hours at a temperature of 0 to 180 ° C. to conduct conductive water dispersibility through the emulsion oxidation polymerization step.
  • Nanoparticles can be prepared.
  • the present invention comprises i) 0.01 to 2,000 parts by weight of a stabilizer relative to 100 parts by weight of a substituted or unsubstituted thiophene, pyrrole or furan monomer and 0.01 to 10 mole ratio of the first oxidizing agent of the monomer.
  • Emulsion preparation step of mixing an acidic aqueous solution of pH 1 to 6 by adding HCl having a temperature range of 0 to 180 °C of 1,000 to 2,000 parts by weight of ii) the second oxidizing agent in the emulsion of step i) 0.001
  • a seed emulsion preparation step of mixing at a molar ratio of about 5.0 to 5.0 and then stirring at 0 to 180 ° C.
  • the conductive water-dispersible nanoparticles may be prepared including an emulsion oxidation polymerization step.
  • drying of the step c) in the present invention may be dried at room temperature-70 ° C. as a step of drying the conductive particles in an emulsion state.
  • the present invention provides a conductive water-dispersible nanoparticles prepared by the above method, wherein the conductive water-dispersible nanoparticles have a size of 10 nm to 1 ⁇ m, and have good processability and high conductivity compared to conventional conductive polymers.
  • the present invention provides an electronic material, an optical material, a toner, and / or an ink prepared from the conductive water dispersible nanoparticles, wherein the polypyrrole, polyfuran, or polythiophene nanoparticles prepared by the present invention have good processability. It can be used in electronic materials, optical materials, toners and / or inks because of its conductivity, and can also be used in energy conversion and energy storage materials, antistatic materials, charge control materials, electrically conductive layer materials, pattern manufacturing materials, printing ink materials, etc. Can be applied.
  • the electronic materials, toners and / or inks according to the present invention mean electronic materials, toners and / or inks including polypyrrole, polyfuran or polythiophene prepared by the present invention, and include such a configuration.
  • Any product in the art would correspond to the electronic materials, toners and / or inks according to the present invention, and preferred electronic materials include photovoltaic cells, capacitors (used as electrolytes) and printed circuit boards (PCBs).
  • Substrate coatings can minimize environmental pollution
  • antistatic agents preventing static electricity generated on surfaces of plastics, polymers, etc. through coating, etc.).
  • the mixture was then mixed with 0.3 g of an aqueous 30% by weight aqueous hydrogen peroxide solution as a first oxidant and 7 mg of ferric sulfate [Fe 2 (SO 4 ) 3 ] as a second oxidant to 5 g of deionized water.
  • a mixed solution containing a second oxidizing agent and the seed emulsion mixture was stirred for 12 hours at a temperature of 25 °C to prepare poly (3.4-ethylenedioxythiophene) particles in the emulsion state.
  • polypyrrole particles in the emulsion state prepared above were dried in a range of room temperature to 70 ° C. to prepare poly (3.4-ethylenedioxythiophene) particles.
  • the conversion rate of the poly (3.4-ethylenedioxythiophene) emulsion was 99%, and the average polypyrrole particle size was 50 nm, which was obtained by using a bar coating method (# 7 bar) to form a conductive film. As a result, 10 5.0 ohm / sq. was obtained.
  • Example 2 In the same manner as in Example 1, 69 g of a 18% by weight polystyrene sulfonic acid solution as a stabilizer was used, and 7 mg of ferric sulfate, a second oxidant, was mixed with 5 g of deionized water as an initiator. After preparing a mixed solution containing the mixture was mixed with the emulsion and reacted for about 30 minutes at a temperature of 25 °C to prepare a seed emulsion.
  • the seed emulsion mixture was then stirred for 12 hours at a temperature of 25 ° C. in a closed reactor to prepare poly (3.4-ethylenedioxythiophene) particles in emulsion state.
  • the conversion rate of the poly (3,4-ethylenedioxythiophene) emulsion was 96%, and the prepared polypyrrole particle size was 10-50 nm, which was obtained by the bar coating method (# 7 bar).
  • the bar coating method # 7 bar.
  • the conductive water dispersible nanoparticles prepared according to the method of the present invention exhibit excellent processability and high conductivity compared to conventionally prepared conductive nanoparticles.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Nanotechnology (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Dispersion Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Conductive Materials (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)

Abstract

Cette invention concerne un procédé de production de nanoparticules conductrices pouvant être dispersées dans l'eau, et plus spécifiquement, un procédé de production de nanoparticules conductrices pouvant être dispersées dans l'eau caractérisé en ce qu'il comprend les étapes suivantes : (a) formation d'une émulsion par mélange d'une solution aqueuse de monomères de thiophène, furanne ou pyrrole ; un composé choisi dans le groupe constitué par HCl, HF, HBr et HI ; un stabilisant ; et un premier oxydant ; (b) incorporation par mélange d'un second oxydant dans l'émulsion de l'étape (a), puis formation des particules conductrices pendant agitation du mélange à l'état d'émulsion ; et (c) séchage des particules conductrices à l'état d'émulsion de l'étape (b). Comparativement à des nanoparticules conductrices pouvant être dispersées dans l'eau préparées par des procédés classiques, les nanoparticules conductrices pouvant être dispersées dans l'eau obtenues selon cette invention font preuve d'une conductivité électrique élevée et d'une excellente aptitude à la mise en œuvre.
PCT/KR2012/004436 2011-06-07 2012-06-05 Procédé de production de nanoparticules conductrices pouvant être dispersées dans l'eau Ceased WO2012169767A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201280028262.8A CN103748032A (zh) 2011-06-07 2012-06-05 导电性水分散性纳米粒子的制造方法

Applications Claiming Priority (2)

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KR1020110054542A KR20120135690A (ko) 2011-06-07 2011-06-07 전도성 수분산성 나노입자의 제조방법
KR10-2011-0054542 2011-06-07

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WO2012169767A2 true WO2012169767A2 (fr) 2012-12-13
WO2012169767A3 WO2012169767A3 (fr) 2013-04-04

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CN (1) CN103748032A (fr)
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Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7338620B2 (en) * 2004-03-17 2008-03-04 E.I. Du Pont De Nemours And Company Water dispersible polydioxythiophenes with polymeric acid colloids and a water-miscible organic liquid
US7351358B2 (en) * 2004-03-17 2008-04-01 E.I. Du Pont De Nemours And Company Water dispersible polypyrroles made with polymeric acid colloids for electronics applications
KR100684913B1 (ko) * 2005-10-06 2007-02-20 연세대학교 산학협력단 티오펜 에멀젼의 산화중합에 의한 폴리티오펜 나노입자와이의 유도체 및 이의 제조방법
CN100590139C (zh) * 2007-04-04 2010-02-17 同济大学 用二苯胺磺酸共聚法合成聚吡咯纳米粒子的方法
KR101003531B1 (ko) * 2008-07-03 2010-12-28 주식회사 제이앤드제이 캐미칼 폴리티오펜 또는 폴리티오펜 유도체가 전도성 유화제로둘러싸여 있는 나노입자 및 그 제조방법
KR101000496B1 (ko) * 2008-09-19 2010-12-14 (주)폴리메리츠 가용성 폴리(3,4-에틸렌다이옥시싸이오펜) 나노분말의 제조방법

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Publication number Publication date
CN103748032A (zh) 2014-04-23
KR20120135690A (ko) 2012-12-17
WO2012169767A3 (fr) 2013-04-04
TW201302844A (zh) 2013-01-16

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