WO2004083283A1 - Procede de preparation de nanoparticules de polyaniline allongees de conductivite elevee par polymerisation microemulsionnee - Google Patents

Procede de preparation de nanoparticules de polyaniline allongees de conductivite elevee par polymerisation microemulsionnee Download PDF

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Publication number
WO2004083283A1
WO2004083283A1 PCT/KR2004/000602 KR2004000602W WO2004083283A1 WO 2004083283 A1 WO2004083283 A1 WO 2004083283A1 KR 2004000602 W KR2004000602 W KR 2004000602W WO 2004083283 A1 WO2004083283 A1 WO 2004083283A1
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Prior art keywords
surfactant
polyaniline
polyaniline nanoparticles
micelle
preparing
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PCT/KR2004/000602
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English (en)
Inventor
Jyongsik Jang
Jung-Suk Ha
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Dongjin Semichem Co. Ltd.
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Publication of WO2004083283A1 publication Critical patent/WO2004083283A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/12—Powdering or granulating
    • C08J3/14—Powdering or granulating by precipitation from solutions
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/02—Polyamines
    • C08G73/026—Wholly aromatic polyamines
    • C08G73/0266—Polyanilines or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
    • C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors

Definitions

  • the present invention relates to a method for preparing polyaniline nanoparticles, and more particularly, to a method for preparing polyaniline nanoparticles having rod shapes and high conductivity using low-temperature micro-emulsion polymerization.
  • the conductive polymer can be utilized in various areas, such as an electromagnetic shielding, an alternative material of Indium tin oxide(ITO), an alternative material of carbon fiber, a magnetic recording medium, an optical storage, a light emitting device(LED), a cathode material of lithium ion battery, a light transmission material, and so on.
  • ITO Indium tin oxide
  • LED light emitting device
  • the polymer When the conductive polymer is produced in the form of nanoparticles, the polymer has more desirable physical properties due to the small sizes of the nanoparticles than a conductive polymer of a bulk form.
  • the nanoparticle is a material having the size of between a molecule and a bulk solid, and generally has the size of 1 to 100 nanometers.
  • the nanoparticle has different magnetic, optical and electrical properties from a molecule and/or a bulk solid, and the specific properties of the nanoparticle are sometimes called as 'Quantum size effect'.
  • the nanoparticle is also sometimes called as 'Quantum dot'.
  • Polyaniline one of the representative conductive polymers, is a black colored polymer which is produced by oxidation-polymerization of aniline monomer in acidic solution, and conventionally called as 'aniline black'.
  • 'aniline black' the conductivity of polyaniline dramatically increases when protonic acid is doped into the polyaniline.
  • polyaniline have attracted much attention in the art as a desirable conductive polymer.
  • polyaniline and its derivatives have further advantages in that they are easy to produce, inexpensive, and have desirable atmospheric and thermal stabilities.
  • polyaniline When an electromagnetic shielding is produced by dispersing polyaniline into other non-conductive polymer matrix, polyaniline should be uniformly dispersed into the matrix, and the two materials should form a uniform complex without inducing phase separations between the two polymers. If polyaniline in the form of nanoparticles is used for this purpose, polyaniline is more uniformly dispersed in the matrix than polyaniline of micro-size particles, and more uniform polyaniline filler/matrix complex can be formed. In addition, as the conductivity of polyaniline filler increases, the conductivity of the complex increases, and more desirable electromagnetic shielding can be obtained. Therefore, there is an increasing need in the art for polyaniline of high conductivity and nanoparticle size. Disclosure of Invention
  • the present invention provides a method for preparing polyaniline nanoparticles by using microemulsion polymerization, which comprises the steps of adding a surfactant into a mixed solvent including water and an organic solvent, and stirring the surfactant to form a micelle; adding aniline monomer into a reaction solution containing the micelle, and polymerizing the aniline monomer with a dopant and an oxidizing agent to form polyaniline; and adding excess organic solvent to the reaction solution to separate the polyaniline and the micelle.
  • the micelle formation step is carried out at the temperature of -30 to 0 ° C
  • the organic solvent in the mixed solvent can be selected from the group consisting of methanol, ethanol, butanol, octanol, decanol and the mixtures thereof, and the amount of the organic solvent is 20 to 40 weight% in the mixed solvent.
  • the method for preparing polyaniline nanoparticles according to the present invention produces polyaniline by carrying out a microemulsion polymerization at very low temperature, and thereby reduces the amount of the surfactant required in the microemulsion polymerization, and improves the conductivity and the yield of the produced polyaniline.
  • micelles should be formed by adding a surfactant into a reaction solvent at the temperature of less than 0 ° C, preferably at the temperature of -30 to -10 ° C, and more preferably at the temperature of about -20 ° C, and stirring the surfactant for 20 to 40 minutes, and preferably for about 30 minutes.
  • the micelle formation step is carried out at the very low temperature. Therefore, in order to prevent the freezing of the solvent, a mixed solvent including water and an organic solvent is used for the micelle formation step.
  • the preferable organic solvent includes methanol, ethanol, butanol, octanol, decanol or the mixtures thereof, and the preferable water is distilled water.
  • the ratio of the organic solvent and water can be varied under the condition that the freezing of the solvent is prevented at the reaction temperature.
  • the preferable and exemplary amount of the organic solvent is 20 to 40 weight% in the mixed solvent, and more preferably about 30 weight%.
  • the amount of the organic solvent is less than 20 weight%, the temperature of the micelle formation step cannot be sufficiently lowered.
  • the amount of the organic solvent is more than 40 weight%, the micelles formation may not be sufficiently carried out.
  • the temperature of the micelle formation step is less than -30 ° C, the micelles formation may not be sufficiently carried out.
  • the temperature of the micelle formation step is more than 0 ° C, the amount of the necessary surfactant cannot be reduced sufficiently.
  • the surfactant which is added to the mixed solvent, can be a cationic surfactant, an anionic surfactant, or the mixtures thereof.
  • the preferable examples of the cationic surfactant include octyltrimethylammonium bromide (OTAB), decyltrimethy- lammonium bromide (DeTAB), dodecyltrimethylammonium bromide (DTAB), and the mixtures thereof.
  • the preferable examples of the anionic surfactant include sodium dodecylsulfate(SDS), sodium dioctylsulfosuccinate and the mixtures thereof.
  • the preferable amount of the surfactant is 0.8 to 2.5 weight part for 100 weight part of the mixed solvent.
  • the micelle When the amount of the surfactant is less than 0.8 weight part, the micelle may not be properly formed. When the amount of the surfactant is more than 2.5 weight part, the micelle may be transformed into undesirable shapes from the rod shape.
  • the amount of the surfactant used in the present invention is about 1/10 compared to the amount of the surfactant used in a microemulsion polymerization at room temperature. This might be due to the fact that (i) CMC decreases at low temperature, and thereby, the concentration of the surfactant can be greater than CMC 2 even when a small amount of the surfactant is used, and (ii) the organic solvent, which is included in the mixed solvent for preventing the solvent from being freezing, works as a cosurfactant.
  • 'CMC represents 'Critical Micelle Concentration' which is a concentration capable of forming micelle by surfactant association, and the shape of the micelle varies according to the type and concentration of the surfactant. Generally, when the concentration of the surfactant is more than CMCl, sphere shaped micelles are formed, and when the concentration of the surfactant is more than CMC2, rod shaped or hexagonal shaped micelles are formed. Meanwhile, when the concentration of the surfactant is between the CMCl and CMC2, the produced micelles are transparent in the solution and invisible by a naked eye. When the concentration of the surfactant is more than CMC2, the produced micelles are invisible by the naked eye and the solution becomes opaque.
  • the shapes of the micelles are difficult to determine by the naked eye. Therefore, the shape of the polymer polymerized in the micelles is observed with apparatus, such as TEM(Transmission Electron Microscope), SEM(Scanning Electron Microscope) and so on, to determine the concentration of the surfactant.
  • apparatus such as TEM(Transmission Electron Microscope), SEM(Scanning Electron Microscope) and so on, to determine the concentration of the surfactant.
  • the CMC 1 and CMC 2 of a surfactant at room temperature are known, the CMC 1 and CMC 2 can be referenced for the purpose of the present invention.
  • stirring of the reaction solution is carried out while adding aniline monomer as the monomer of the conductive polymer.
  • a dopant and an oxidizing agent are added thereto to initiate the polymerization reaction.
  • the preferable amount of the aniline monomer is about 0.75 to 2.5 weight part for 100 weight part of the mixed solution containing micelles.
  • the amount of the aniline monomer is less than 0.75 weight part, all of the micelle may not be used as a nano-reactor.
  • the amount of the aniline monomer is more than 2.5 weight part, the micelles may not receive all of the aniline monomer, and the deformation of micelles may occur.
  • the dopant is used to increase the conductivity of the polymerized polyaniline, and to adjust the acidic condition of the reaction solution for rapid and stable reaction.
  • exemplary dopant includes protonic acid such as hydrochloric acid, sulfuric acid, phosphoric acid, the mixtures thereof, and so on.
  • sulfuric acid is more preferable than hydrochloric acid as the dopant.
  • the preferable amount of the dopant is 1 to 3 moles for 1 mole of the aniline monomer. When the amount of the dopant is less than 1 mole, the conductivity of the produced polymer may not be satisfactory. When the amount of the dopant is more than 3 moles, the conductivity of the produced polymer does not additionally increase, but the phase of the polymer may be deformed.
  • the oxidizing agent is used to polymerize the aniline monomer, and the examples of the oxidizing agent includes ammonium persulfate ((NH ) S O ), potassium perox-
  • the preferable amount of the oxidizing agent is 0.2 to
  • the more preferable amount is about 0.5 mole for 1 mole of the aniline monomer.
  • the amount of the oxidizing agent is less than 0.2 mole, the polymerization of the aniline monomer may not be satisfactory. Even when the amount of the oxidizing agent is more than 0.8 mole, the polymerization speed of the aniline monomer and the polymerization efficiency may not further increase.
  • the oxidizing agent can be added to the reaction solution containing the aniline monomer and the dopant.
  • the oxidizing agent can be dissolved with a dopant, such as hydrochloric acid, sulfuric acid, and so on, and the mixture of the oxidizing agent and the dopant can be added to the reaction solution containing the aniline monomer. More preferably, the oxidizing agent and the dopant are added to the reaction solution after stirring the solution containing micelles and the aniline monomer for about 30 minutes. During the stirring, the aniline monomers are fully incorporated into the interior of the micelles.
  • the reaction time of the polymerization reaction is about 8 to 16 hours, and preferably about 12 hours, and the reaction temperature is preferably maintained to be same with the reaction initiation temperature.
  • the surfactant is removed to separate the polyaniline nanoparticles produced in the micelles.
  • the reaction solution is poured into a separatory funnel, and excess organic solvent such as methanol, acetone, the mixtures thereof, and so on, is added thereto. Then the surfactant and the reaction by-products dissolve and are moved into the organic layer. By discarding the upper organic layer, an aqueous solution containing precipitated polyaniline nanoparticles is obtained. Then, by evaporating the aqueous solution at room temperature, the target polyaniline nanoparticles can be obtained.
  • reaction temperature was maintained to -20 ° C with a temperature controlling bath, and a mixed solvent including 40 mi of distilled water and 20 mi of ethanol was used as a reaction medium.
  • a mixed solvent including 40 mi of distilled water and 20 mi of ethanol was used as a reaction medium.
  • 0.5g of decyltrimethylammonium bromide was added to the mixed solvent, and stirred for about 20 minutes to form micelles.
  • lg of aniline monomer was dropwisely added to the reaction solution by a pipette. The added aniline monomer further stirred for 30 minutes to fully insert the aniline monomer into the interior of the micelles.
  • the upper layer of the reaction solution i.e., the methanol layer was removed by using a pipette, and the remaining layer containing nanoparticles was evaporated at room temperature.
  • the formation of the polyaniline nanoparticles was confirmed with FT-IR analysis. From the TEM(Transmission Electron Microscopy) analysis of the obtained polyaniline nanoparticles, it is confirmed that the rod shaped nanoparticle having the width of about 20 nanometers and the length of about several hundreds nanometer is produced.
  • the conductivity of the obtained nanoparticle was 50 to 80 S/cm.
  • polyaniline nanoparticles were produced according to the method described in Example 1. The formation of the polyaniline nanoparticles was confirmed with FT-IR analysis. From the TEM(Transmission Electron Microscopy) analysis of the obtained polyaniline nanoparticles, it is confirmed that the rod shaped nanoparticle having the width of several tens nanometers and the length of about several hundreds nanometer is produced.
  • polyaniline nanoparticles were produced according to the method described in Example 1.
  • the formation of the polyaniline nanoparticles was confirmed with FT-IR analysis. From the TEM(Transmission Electron Microscopy) analysis of the obtained polyaniline nanoparticles, it is confirmed that the rod shaped nanoparticle having the width of several tens nanometers and the length of about several hundreds nanometer is produced.
  • the conductivity of the obtained nanoparticle was 150 to 200 S/ ⁇ which is much higher than the conductivity of polyaniline nanoparticles produced with a cationic surfactant.
  • the method for preparing polyaniline nanoparticles according to the present invention performs the microemulsion polymerization at very low temperature of about -20 ° C. Therefore, the amount of the surfactant required for the microemulsion polymerization is reduced to about 1/10 compared to the amount of the surfactant used in a microemulsion polymerization at room temperature, which reduces the cost for producing polyaniline nanoparticles, and increases the yield of the polyaniline nanoparticles. Since the small amount of the surfactant is used in the present invention, the washing step for removing the micelles, which is produced with the surfactant, from the produced polyaniline nanoparticles can be greatly simplified.
  • the polyaniline nanoparticles produced according to the present invention has the high conductivity of 200 to 300 S/ ⁇ and is useful as an electro ⁇ nagnetic material, such as an anti-static agent, an electromagnetic shielding, a magnetic recording medium, a gas sensor, an electron transport layer of a light emitting device, and so on, and is particularly suitable as a nano-cable, an alternative material of carbon fiber, and so on due to its rod shape.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

L'invention concerne un procédé de préparation de nanoparticules de polyaniline de forme allongée et de conductivité élevée par polymérisation microémulsionnée. Ledit procédé consiste à ajouter un tensioactif dans un solvant mélangé comprenant de l'eau et un solvant organique, et agiter le tensioactif pour former une micelle, de préférence à la température entre -30 et O °C ; à ajouter un monomère d'aniline dans une solution réactionnelle contenant la micelle et polymériser ledit monomère avec un dopant et un agent oxydant pour former la polyaniline ; et à ajouter un solvant organique en excès à la solution réactionnelle pour séparer la polyaniline et la micelle.
PCT/KR2004/000602 2003-03-20 2004-03-19 Procede de preparation de nanoparticules de polyaniline allongees de conductivite elevee par polymerisation microemulsionnee WO2004083283A1 (fr)

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KR10-2003-0017516 2003-03-20
KR1020030017516A KR100858839B1 (ko) 2003-03-20 2003-03-20 초저온 마이크로에멀젼 중합을 이용한 고전도성 막대형폴리아닐린 나노 입자의 제조 방법

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Cited By (9)

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Publication number Priority date Publication date Assignee Title
EP1736137A1 (fr) * 2005-06-22 2006-12-27 L'Oréal Particule colorée optiquement et une structure optique
CN100402583C (zh) * 2006-03-03 2008-07-16 扬州大学 聚苯胺纳米粒子合成方法
CN100497440C (zh) * 2005-04-19 2009-06-10 中国科学院金属研究所 一种聚苯胺微/纳米纤维的制备方法
US7683124B2 (en) 2004-01-23 2010-03-23 Ormecon Gmbh Dispersions of intrinsically conductive polymers, and methods for the production thereof
US7718164B2 (en) 2005-06-22 2010-05-18 L'oreal S.A. Optically colored body and optical structure
US7947199B2 (en) * 2005-03-02 2011-05-24 Ormecon Gmbh Conductive polymers consisting of anisotropic morphology particles
CN102702516A (zh) * 2012-05-28 2012-10-03 东华大学 一种多元掺杂制备聚苯胺的方法
CN104629071A (zh) * 2015-02-03 2015-05-20 中南大学 一种表面负载有稀土铈离子的聚苯胺中空微球的制备方法
CN111234525A (zh) * 2020-02-18 2020-06-05 浙江理工大学 一种掺杂型聚苯胺/纳米微晶纤维素复合材料的制备方法

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CN112778969A (zh) * 2020-12-21 2021-05-11 安徽理工大学 一种凹凸棒/聚苯胺复合材料的制备方法

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KR100656872B1 (ko) * 2001-02-07 2006-12-12 주식회사 새 한 유기용매 가용성 폴리아닐린의 제조방법

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US5240797A (en) * 1988-04-30 1993-08-31 Seiko Epson Corporation Thin film device and method of manufacture
US5242558A (en) * 1988-04-30 1993-09-07 Seiko Epson Corporation Method for forming a thin film device
KR20030021278A (ko) * 2001-09-05 2003-03-15 주식회사 포스코 가용성 폴리(아닐린-공-안트라닐산) 마이크로 에멀션중합체 제조방법, 이로부터 제조된 마이크로 에멀션중합체 및 이러한 마이크로에멀션 중합체가 적용된 철강또는 금속 제품

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7683124B2 (en) 2004-01-23 2010-03-23 Ormecon Gmbh Dispersions of intrinsically conductive polymers, and methods for the production thereof
US7947199B2 (en) * 2005-03-02 2011-05-24 Ormecon Gmbh Conductive polymers consisting of anisotropic morphology particles
CN101133104B (zh) * 2005-03-02 2011-06-29 沃明创有限公司 由具有各向异性形态粒子构成的导电聚合物
CN100497440C (zh) * 2005-04-19 2009-06-10 中国科学院金属研究所 一种聚苯胺微/纳米纤维的制备方法
EP1736137A1 (fr) * 2005-06-22 2006-12-27 L'Oréal Particule colorée optiquement et une structure optique
US7718164B2 (en) 2005-06-22 2010-05-18 L'oreal S.A. Optically colored body and optical structure
CN100402583C (zh) * 2006-03-03 2008-07-16 扬州大学 聚苯胺纳米粒子合成方法
CN102702516A (zh) * 2012-05-28 2012-10-03 东华大学 一种多元掺杂制备聚苯胺的方法
CN104629071A (zh) * 2015-02-03 2015-05-20 中南大学 一种表面负载有稀土铈离子的聚苯胺中空微球的制备方法
CN104629071B (zh) * 2015-02-03 2018-05-15 中南大学 一种表面负载有稀土铈离子的聚苯胺中空微球的制备方法
CN111234525A (zh) * 2020-02-18 2020-06-05 浙江理工大学 一种掺杂型聚苯胺/纳米微晶纤维素复合材料的制备方法

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TWI282345B (en) 2007-06-11
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TW200420617A (en) 2004-10-16

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