KR20170092343A - Synthesis method of metal-polyaniline composite - Google Patents
Synthesis method of metal-polyaniline composite Download PDFInfo
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- KR20170092343A KR20170092343A KR1020160013566A KR20160013566A KR20170092343A KR 20170092343 A KR20170092343 A KR 20170092343A KR 1020160013566 A KR1020160013566 A KR 1020160013566A KR 20160013566 A KR20160013566 A KR 20160013566A KR 20170092343 A KR20170092343 A KR 20170092343A
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- 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
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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
- C08J3/20—Compounding polymers with additives, e.g. colouring
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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
- C08J3/28—Treatment by wave energy or particle radiation
Abstract
The present invention relates to a method for synthesizing a metal-polyaniline composite, and more particularly, to a method for synthesizing a metal-polyaniline composite, which comprises mixing pure pure aniline monomer in liquid state with a metal precursor without additional oxidizing agent, Polyaniline composite which can appropriately determine and control the shape of the polyaniline composite, increase the uniformity of the shape, and prevent the decrease in physical properties of the polyaniline due to the use of an excessive amount of the oxidant.
The metal-polyaniline composite synthesized in a certain shape according to the present invention can be utilized as materials in various fields including electronic devices, optical devices, catalysts, and energy-related devices.
Description
The present invention relates to a method for synthesizing a metal-polyaniline composite, and more particularly, to a method for synthesizing a metal-polyaniline composite, which comprises mixing pure pure aniline monomer in liquid state with a metal precursor without additional oxidizing agent, Polyaniline composite which can appropriately determine and control the shape of the polyaniline composite, increase the uniformity of the shape, and prevent the decrease in physical properties of the polyaniline due to the use of an excessive amount of the oxidant.
The metal-polyaniline composite synthesized in a certain shape according to the present invention can be utilized as materials in various fields including electronic devices, optical devices, catalysts, and energy-related devices.
Polymers are used in a variety of fields, from everyday life to engineering. The reason for this is that it is stable, has chemical properties, and exhibits various properties depending on the monomer, degree of polymerization and polymerization method. In addition, in the case of engineering plastics added with carbon fiber or glass fiber, the physical properties can be dramatically increased, so that they can be used as components and building materials for precision machinery requiring higher physical properties. In particular, the invention of conductive polymer has been a catalyst for overcoming the limit of application range of polymer. As the polymer becomes electrically conductive and can be used as a material for electronic devices replacing existing metal materials, the conductive polymer becomes a key material in organic electronic devices such as flexible displays.
Unlike general polymer materials, polyaniline is not only environmentally stable, but also exhibits electrical, thermoelectric and optical performance, and thus has attracted great attention as a material for next generation electronic devices. In particular, conductive polyaniline is expected to be widely used as a material for various electronic devices such as a secondary battery, a solar cell, a sensor, and a light emitting diode.
These polyanilines are mainly synthesized by oxidizing the unit aniline (aniline). Two types of chemical synthesis and electrochemical synthesis are largely performed according to the method of oxidizing aniline. The chemical synthesis is generally a method of polymerizing aniline using an oxidizing agent such as ammonium persulfate under an aqueous solution. If necessary, various acids such as hydrochloric acid, sulfuric acid, and nitric acid may be added. In contrast, in the electrochemical synthesis method, polyaniline is synthesized by electrochemically oxidizing aniline without a separate oxidant. However, the electrochemical synthesis method is relatively low in productivity due to the nature of the method, and is mainly used for a specific purpose such as polyaniline thin film formation.
That is, for the commercialization of polyaniline, a chemical synthesis method having a relatively simple polymerization method and a high yield is advantageous. In order to improve the electrical / optical properties of polyaniline, it is necessary to change the structure of the polyaniline by doping the polyaniline. Doping is a method of increasing conductivity by protonating a proton to an imino group through acid treatment of polyaniline, and it is also possible to change the characteristics depending on the kind of acid used in the acid treatment have.
The characteristics of the polyaniline vary depending on the conditions of the chemical synthesis method such as the reaction temperature, the concentration of the reactant, and the additives. However, it is difficult to predict the physical properties of the synthesized polyaniline because the ionic strength of the excessively added oxidizing agent and the solution has a large influence on the polyaniline synthesis. In particular, it is known that the oxidant added more than necessary in the synthesis reaction significantly lowers the physical properties of polyaniline. Therefore, it is very important to control the concentration of the oxidizing agent.
On the other hand, in order to actually use polyaniline as an electronic material, it is necessary to control its size and shape. Generally known polyaniline forms are amorphous, small fragments and spherical forms which have no uniform form, and they have been reported to be made into fibers in accordance with the synthesis method. A basic method for controlling the shape of polyaniline is a method using a template. These templates are roughly classified into two types: a hard template such as a zeolite, an opal and a membrane; a soft template such as a block polymer and a surfactant; template). The synthesis of polyaniline using this template makes a great contribution to the formation of micro or nano-sized shapes and enables control of shape. However, the method using a template has a problem that it is difficult to obtain a highly pure polyaniline, and a process for removing a template after polyaniline polymerization is required, which is troublesome.
Recently, methods for controlling the shape without using a template such as an interfacial polymerization method have been studied, but the process is complicated and the yield is low. In particular, the synthetic methods until now still remain simple shapes such as dots and lines, but they do not reach a perfect planar or three-dimensional structure, which hinders the expansion of polyaniline utilization.
In addition, in order to completely replace the existing electronic materials, polyaniline needs to further improve its physical / electrical properties, and there is a method of mixing polyaniline and metal to achieve this. The mixing of these metals can impart additional functions to the polyaniline, which can broaden its application range. However, most of the metal-polyaniline mixtures are often close to amorphous, which does not show a uniform shape, and it is difficult to control the shape, so that practical application to electronic materials is limited.
DISCLOSURE Technical Problem The present invention has been made to overcome the problems of the prior art as described above, and it is an object of the present invention to provide a method of manufacturing a metal-polyaniline composite which is based on the chemical synthesis method of polyaniline, It is a technical object of the present invention to provide a novel and simple method of synthesizing a metal-polyaniline composite which can greatly improve uniformity of size and maximize utilization in various fields such as electronic devices.
In order to accomplish the above object, the present invention provides a method for preparing a composite material, comprising the steps of: a) mixing pure aniline monomer in a liquid state as a reactant with metal salt as a metal precursor and forming a complex through oxidation- step; b) radiating ultrasound to the mixture of monomer and metal precursor in reaction to maintain uniformity of the composite shape; And c) terminating the polymerization reaction and increasing the molecular weight by placing a rest period, wherein the shape of the metal-polyaniline composite synthesized according to the kind of the metal precursor used in step a) Wherein the metal-polyaniline composite is a metal-polyaniline composite.
According to another aspect of the present invention, there is provided a multi-functional metal-polyaniline composite which is synthesized by the above-described method and whose shape is controlled uniformly and uniformly.
According to the present invention, in the polymer polymerization of polyaniline, it is possible to synthesize an aniline monomer and a metal salt through a redox reaction (electron exchange) without using an oxidizing agent like the conventional synthetic method, Negative effects can be ruled out.
In particular, since the shape of the metal-polyaniline composite can be controlled according to the added metal salt, it is possible to realize diversification of the shape of the polyaniline which has remained in the prior art or the prior art, and the shape (shape and size) And also has the advantage of being able to increase the uniformity of the light.
In addition, unlike the conventional method of controlling the shape of polyaniline using a template, a metal-polyaniline complex having an effectively controlled shape can be synthesized through a simple process.
As described above, the metal-polyaniline composite synthesized according to the present invention can be used as a material for various electronic devices or optical devices such as a flexible display, and further, by using a metal material contained therein as a catalyst It can also be applied to energy related fields.
1 is a block diagram schematically showing a process for synthesizing a metal-polyaniline composite according to the present invention.
2 is a schematic view of an ultrasonic horn device used in the synthesis of a metal-polyaniline composite according to an embodiment of the present invention.
3 is a schematic view of an ultrasonic cleaner device used in the synthesis of a metal-polyaniline complex according to an embodiment of the present invention.
4 is a scanning electron micrograph of a platinum-polyaniline composite synthesized according to an embodiment of the present invention.
5 is an optical microscope photograph of a platinum-polyaniline composite synthesized according to an embodiment of the present invention.
6 is a scanning electron micrograph of a palladium-polyaniline composite synthesized according to an embodiment of the present invention.
FIG. 7 is a scanning electron microscope (SEM) image of a platinum-polyaniline composite according to an embodiment of the present invention.
Hereinafter, the present invention will be described in detail.
The method of synthesizing a metal-polyaniline composite according to the present invention is a method of synthesizing a metal-
a) mixing a pure aniline monomer in a liquid state as a reactant with a metal salt as a metal precursor to form a complex through oxidation-reduction reaction without adding an oxidizing agent;
b) radiating ultrasound to the mixture of monomer and metal precursor in reaction to maintain uniformity of the composite shape; And
c) placing a rest period, terminating the polymerization reaction and increasing the molecular weight,
The shape of the metal-polyaniline composite synthesized according to the kind of the metal precursor used in the step a) is controlled differently (see FIG. 1).
The step a) is a step of mixing only an aniline monomer and a metal precursor as a reactant, forming a complex through reduction of a metal and oxidation of aniline without addition of an oxidizer, The shape of the metal-polyaniline complex is specifically determined depending on the type.
The aniline is an aniline salt such as aniline hydrochloride or an aniline solution in which aniline is dissolved in a solvent. It is a pure aniline monomer and is present as a liquid at room temperature. It is used as a solvent for dissolving metal salts and as a monomer for polyaniline polymerization. The aniline refers to a benzene ring having an amine group, and a benzene ring or an alkyl chain may be added to the aniline if necessary. In addition, the present invention exemplifies aniline monomers for synthesizing metal-polyaniline complexes. However, in addition to the aniline monomers, monomers of conductive polymers such as pyrrole and thiophene; And monomers of all polymers polymerized by polymerisation through oxidation polymerization, pure organic substances present in a liquid state at a certain temperature can be a substitute for the aniline monomers.
The metal precursor is a reactant and is an element for controlling the shape of a metal-polyaniline composite to be synthesized. The metal precursor is a metal precursor of iron, cobalt, nickel, copper, zinc, ruthenium Ru, Rh, Pd, Ag, Cd, Os, Ir, Pt, Au, Zr, Bi, tantalum (Ta), manganese (Mn), aluminum (Al) and cerium (Ce) may be used singly or in combination of two or more.
In one embodiment, the metal precursor may be a chlorinated platinic acid (chloroplatinic acid hexahydrate, H 2 PtCl 6 .6H 2 O). In this case, the metal precursor may be a hexagonal plate- A polyaniline composite is finally obtained.
In another embodiment, the metal precursor may be potassium tetrachloropalladate (K 2 PdCl 4 ). In this case, a palladium-polyaniline complex whose shape is controlled in the form of a hexahedron is finally obtained.
This step may further include a step of mixing the aniline monomer and the metal precursor and then removing dissolved oxygen through air purging. At this time, the air exhaust can be performed using at least one inert gas selected from nitrogen (N 2 ), argon (Ar), helium (He), xenon (Xe), krypton (Kr) and neon (Ne).
Specifically, this step is carried out by mixing 10 mM to 500 mM of the metal salt of the above-mentioned kind with aniline in a liquid state, stirring the mixture at 0 ° C to 50 ° C for 30 minutes or more, To maintain the temperature constant at 0 占 폚 to 180 占 폚 and, at the same time, air venting for 10 minutes to 500 minutes using an inert gas as described above.
The complex formed in this step may be a metal-polyaniline complex or a metal-oligomer complex. That is, the polyaniline itself may be synthesized through this step, or an oligomeric material may be synthesized. In any case, the polyaniline is finally obtained as a metal-polyaniline complex after the durability step described later.
The step b) is a step of increasing the uniformity of the shape of the composite (e.g., metal-polyaniline complex) by applying ultrasonic waves to the mixture of the monomer and the metal precursor in the reaction.
In this step, the ultrasonic waves can be radiated using various ultrasonic generators such as an ultrasound horn or an ultrasonic horn or an ultrasonic cleaner.
The ultrasonic wave emission frequency of the ultrasonic wave generating device may be 20 kHz to 100 kHz, the ultrasonic wave output may be 1 W to 100 W, and the ultrasonic wave irradiation time may be 1 to 500 hours. In the ultrasonic wave irradiation, , 0 占 폚 to 90 占 폚).
In the step c), the reaction product after the step b) is subjected to a resting period at a predetermined temperature and for a period of time so that the polymerization reaction is terminated and the molecular weight is increased.
In one embodiment, this step can be performed by storing the resultant ultrasonic wave treated at a constant temperature of 10 ° C to 180 ° C (for example, 10 ° C to 100 ° C) for 12 hours to 500 hours without any additional chemical treatment.
Further, a step of adding a metal salt to induce further polymerization reaction may be further performed after this step. The metal salt to be added at this time may be the same or different from the metal salt used in step a), preferably the same kind of metal salt is used again.
After the steps a) to c), a separation step and a collection step for substantially ensuring the synthesized metal-polyaniline composite may be additionally performed.
The separation of the synthesized metal-polyaniline complex can be performed using a centrifugal separator. For example, the product can be separated by centrifugation at a rate of 100 rpm to 10000 rpm for 10 minutes to 300 minutes for 1 to 10 times have. As the solvent, deionized water or an organic solvent such as ethanol, acetone, or isopropanol may be used.
The step of collecting the synthesized metal-polyaniline complex may be carried out using a membrane filter. For example, the separated product may be collected using a membrane filter having a pore size of 0.1 μm to 10 μm . The synthesis process according to the present invention can also be completed by drying the metal-polyaniline composite thus collected at a temperature of 10 ° C to 50 ° C under atmospheric or vacuum conditions.
According to another aspect of the present invention, there is provided a metal-polyaniline composite synthesized according to the above-described method of the present invention.
The metal-polyaniline composite of the present invention has a specific shape according to the metal salt used in the synthesis, and the uniformity in shape and size is greatly improved through the ultrasonic treatment. The metal-polyaniline composite of the present invention can be used not only as a material for an organic electronic device and an organic optical device, but also as a catalyst for a chemical reaction.
Hereinafter, the present invention will be described more specifically by way of examples. However, these examples are provided only for the understanding of the present invention, and the scope of the present invention is not limited to these examples in any sense.
Example 1: Synthesis of platinum-polyaniline complex controlled in hexagonal plate shape
(1) Mixing of aniline and metal precursor
20 mM chloroplatinic acid (H 2 PtCl 6 .6H 2 O) and 10 ml of aniline (liquid) were mixed and stirred at room temperature for 30 minutes. After stirring, the color of the mixture changed from transparent orange to dark black. The completely mixed mixture was air-evacuated for 30 minutes using argon (Ar) as an inert gas.
(2) Ultrasonic radiation and rest
(1), ultrasonic waves were emitted for 3 hours at an output of 8 W using an ultrasonic horn (generated at 20 kHz). During the ultrasonic irradiation, the temperature of the solution was kept constant at 10 ° C by using a thermostat, and after the ultrasonic irradiation, the solution was stored at room temperature for about 24 hours.
(3) Separation and collection
The platinum-polyaniline composite synthesized through the above-described ultrasonic irradiation and the rest period was separated from the unreacted material for 30 minutes using a centrifuge (10000 rpm). After centrifugation, the separated platinum-polyaniline complex was redispersed in ethanol, and the platinum-polyaniline complex was collected by filtration using a membrane filter (pore size: 0.45 μm), and then dried completely at room temperature. The color of the dried platinum-polyaniline complex was confirmed to be purple.
Example 2: Synthesis of palladium-polyaniline complex having a shape controlled in hexahedral form
Except that potassium palladium tetrachloride (K 2 PdCl 4 ) was used instead of the hexachloroplatinic acid as the metal precursor.
Experimental Example: Confirmation of shape and uniformity of synthesized metal-polyaniline composite
(1) Scanning electron microscope photograph of platinum-polyaniline composite
Scanning electron micrographs of the platinum-polyaniline composite synthesized and collected according to Example 1 are shown in FIG.
It can be confirmed that the synthesized platinum-polyaniline composite is relatively uniform in size and shape. The average size of the single platinum-polyaniline complex crystals was about 1 μm in width, about 4.7 μm in length, and about 0.3 μm in height.
(2) Optical microscope photograph of platinum-polyaniline composite
An optical microscope photograph of the platinum-polyaniline composite synthesized and collected according to Example 1 is shown in FIG.
An optical microscope photograph also confirmed that the platinum-polyaniline complex was uniformly formed.
(3) Scanning electron microscope photograph of the palladium-polyaniline complex
SEM photographs of the palladium-polyaniline composite synthesized and collected according to Example 2 are shown in FIG.
It was confirmed that, when a palladium salt was used as a metal precursor, a shape different from that in the case of using a platinum salt was obtained. That is, the shape of the platinum-polyaniline composite synthesized according to Example 1 was controlled by a hexagonal plate shape, while the shape of the palladium-polyaniline composite synthesized according to Example 2 was controlled by a hexahedron.
These results indicate that the shape of the polyaniline is determined by the metal salt in the synthesis of the metal-polyaniline composite according to the present invention, and the shape of the polyaniline can be controlled by changing the metal salt.
(4) Difference in uniformity depending on presence or absence of ultrasonic treatment
FIG. 7 is a scanning electron micrograph of a platinum-polyaniline composite prepared by the addition of an ultrasonic wave and that of a synthesized platinum-polyaniline composite.
In the case of not applying ultrasonic waves (left drawing), a part of the hexagonal plate could be confirmed, but the shape was very irregular. On the other hand, a platinum-polyaniline composite in the form of a hexagonal plate having a comparatively uniform shape and size was obtained when ultrasonic waves were synthesized (right drawing).
These results show that ultrasonic waves can increase the uniformity of the shape.
(5) Review the results
The present invention is advantageous in that a metal-polyaniline complex can be formed using an aniline monomer and a metal precursor without a separate oxidant, and there is no influence of reduction of physical properties due to an excessive oxidant.
In addition, according to the synthesis method of the present invention, the polyaniline is out of the conventional fiber (straight line) shape due to the metal precursor, and has a three-dimensional (or completely flat) shape, and its shape can be controlled according to the incorporated metal salt .
Furthermore, it has been suggested that the uniformity of the shape can be improved by using ultrasonic waves during synthesis.
That is, the metal-polyaniline composite whose shape is controlled through the synthesis method according to the present invention can be used as a material for various electronic devices and can be applied to the energy related field by using a metal contained in the metal-polyaniline composite as a catalyst It is expected that the possibility is high.
Claims (16)
b) radiating ultrasound to the mixture of monomer and metal precursor in reaction to maintain uniformity of the composite shape; And
c) placing a rest period, terminating the polymerization reaction and increasing the molecular weight,
Characterized in that the shape of the metal-polyaniline composite synthesized according to the kind of the metal precursor used in the step a) is controlled differently.
Synthesis method of metal-polyaniline complex.
The metal precursor of step a) may be at least one selected from the group consisting of Fe, Co, Ni, Cu, Zn, Ru, Rh, Pd, Ag, cadmium, osmium, iridium, platinum, gold, zirconium, bismuth, tantalum, manganese, Wherein the metal salt is at least one metal selected from the group consisting of aluminum (Al) and cerium (Ce).
Wherein the metal precursor is chloroplatinic acid hexahydrate (H 2 PtCl 6揃 6H 2 O), and the shape of the hexagonal plate-shaped platinum-polyaniline complex is obtained.
Wherein the metal precursor is potassium tetrachloropalladate (K 2 PdCl 4 ), and the palladium-polyaniline complex having a shape controlled in a hexahedral form is obtained.
Wherein the step a) further comprises a step of mixing the aniline monomer and the metal precursor and then removing dissolved oxygen through air purging.
Characterized in that the air exhaust is carried out using at least one inert gas selected from nitrogen (N 2 ), argon (Ar), helium (He), xenon (Xe), krypton (Kr) - polyaniline complex.
Wherein the composite formed in step a) is a metal-polyaniline composite or a metal-oligomer composite.
Wherein the ultrasound emission in the step b) is performed using an ultrasound horn or an ultrasonic cleaner.
Wherein the ultrasonic wave irradiation in step b) is performed at an ultrasonic frequency of 20 kHz to 100 kHz, an ultrasonic output of 1 W to 100 W, an ultrasonic wave irradiation time of 1 minute to 500 hours, and a constant temperature of 0 ° C to 180 ° C. Synthesis method of polyaniline complex.
Wherein the step c) is performed by storing the resultant of ultrasonic wave irradiation treatment at a constant temperature of 10 ° C to 180 ° C for 12 hours to 500 hours without any chemical treatment.
Further comprising the step of adding a metal salt to induce further polymerization reaction after the step c).
And separating and collecting the metal-polyaniline composite synthesized after the step c).
Separating the metal-polyaniline complex using a centrifugal separator, and collecting the metal-polyaniline composite using a membrane filter.
Wherein the metal-polyaniline composite is used as a material of an organic electronic device or an organic optical device.
Wherein the metal-polyaniline composite is used as a catalyst for a chemical reaction.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20190066257A (en) | 2017-12-05 | 2019-06-13 | 주식회사 파라 | A method for preparing a polyaniline complex for removing antimicrobial and heavy metals in which a polyaniline conductive polymer is doped with an organic acid and a metal ion in a predetermined order, and a polyaniline complex manufactured using thereof |
| KR20190089576A (en) | 2018-01-23 | 2019-07-31 | 주식회사 파라 | A method for preparing a polyaniline complex for removing antimicrobial and heavy metals in which a polyaniline conductive polymer is doped with an organic acid and a metal ion in a predetermined order, and a polyaniline complex manufactured using thereof |
| CN110922589A (en) * | 2019-12-06 | 2020-03-27 | 河南科技大学 | Liquid-liquid interface preparation method of micro-nano structure poly (o-ethoxyaniline) |
| KR20200048706A (en) | 2018-10-30 | 2020-05-08 | 주식회사 파라 | Filter using nanoporous polyaniline complex |
| CN114937766A (en) * | 2022-05-31 | 2022-08-23 | 济宁学院 | Preparation method of transition metal doped poly (m-phenylenediamine) -coated positive electrode material |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2013018732A1 (en) * | 2011-08-01 | 2013-02-07 | 独立行政法人物質・材料研究機構 | Precipitation method for conductive polymer-metal complex, and conductive polymer-metal complex |
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| KR20190066257A (en) | 2017-12-05 | 2019-06-13 | 주식회사 파라 | A method for preparing a polyaniline complex for removing antimicrobial and heavy metals in which a polyaniline conductive polymer is doped with an organic acid and a metal ion in a predetermined order, and a polyaniline complex manufactured using thereof |
| KR20190089576A (en) | 2018-01-23 | 2019-07-31 | 주식회사 파라 | A method for preparing a polyaniline complex for removing antimicrobial and heavy metals in which a polyaniline conductive polymer is doped with an organic acid and a metal ion in a predetermined order, and a polyaniline complex manufactured using thereof |
| US10829592B2 (en) | 2018-01-23 | 2020-11-10 | Para Co., Ltd. | Method for preparing polyaniline complex with antimicrobial activity and heavy metal removal efficiency using conductive poly aniline polymer doped with organic acid and metal ion in defined order |
| KR20200048706A (en) | 2018-10-30 | 2020-05-08 | 주식회사 파라 | Filter using nanoporous polyaniline complex |
| CN110922589A (en) * | 2019-12-06 | 2020-03-27 | 河南科技大学 | Liquid-liquid interface preparation method of micro-nano structure poly (o-ethoxyaniline) |
| CN110922589B (en) * | 2019-12-06 | 2022-05-03 | 河南科技大学 | Liquid-liquid interface preparation method of micro-nano structure poly (o-ethoxyaniline) |
| CN114937766A (en) * | 2022-05-31 | 2022-08-23 | 济宁学院 | Preparation method of transition metal doped poly (m-phenylenediamine) -coated positive electrode material |
| CN114937766B (en) * | 2022-05-31 | 2023-10-31 | 济宁学院 | Preparation method of transition metal doped poly (m-phenylenediamine) coated positive electrode material |
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