CN116874916A - Modified polyaniline conductive plastic and preparation method thereof - Google Patents

Modified polyaniline conductive plastic and preparation method thereof Download PDF

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CN116874916A
CN116874916A CN202311080367.4A CN202311080367A CN116874916A CN 116874916 A CN116874916 A CN 116874916A CN 202311080367 A CN202311080367 A CN 202311080367A CN 116874916 A CN116874916 A CN 116874916A
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parts
acid
aniline polymer
polyaniline conductive
modified polyaniline
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请求不公布姓名
章小婧
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Zhejiang Yongtong New Material Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/04—Homopolymers or copolymers of ethene
    • C08L23/06—Polyethene
    • 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
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
    • 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
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
    • C08G12/06—Amines
    • C08G12/08—Amines aromatic
    • 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
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
    • C08G12/34—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds and acyclic or carbocyclic compounds
    • 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
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/40—Chemically modified polycondensates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08L61/32—Modified amine-aldehyde condensates

Abstract

The invention discloses a modified polyaniline conductive plastic and a preparation method thereof, wherein the modified polyaniline conductive plastic comprises the following components: 50-70 parts of aniline polymer, 10-20 parts of carboxylic acid protonic acid, 5-20 parts of metal salt, 70-120 parts of PE resin, 1-2 parts of talcum powder and 10-15 parts of polyethylene wax; the aniline polymer is prepared by reacting terephthalaldehyde with diamine compounds through Schiff base, and the Schiff base, the protonic acid and the metal salt form a coordination structure, so that the conductivity and the cycling stability of the material can be improved.

Description

Modified polyaniline conductive plastic and preparation method thereof
Technical Field
The invention belongs to the field of conductive polymer materials, and particularly relates to a modified polyaniline conductive plastic and a preparation method thereof.
Background
Polyaniline, polypyrrole and polythiophene are common conductive polymers in the prior art, and polyaniline has better biocompatibility because of wide and easily available raw material sources, thus becoming popular research and development. Polyaniline has the following disadvantages as a conductive material and an electrode material: (1) poor durability and stability: polyaniline conductive materials are susceptible to air oxidation, solvent burning, humidity and temperature, resulting in reduced conductive properties; (2) acid-base vulnerability: polyaniline conductive materials are sensitive to acid-base environments and are easy to be chemically corroded, so that the conductivity is reduced; (3) poor mechanical properties: the polyaniline conductive material has poor mechanical strength and rigidity and is easy to break and deform; (4) poor cycle stability: because polyaniline materials are easy to agglomerate, expansion or shrinkage is easy to occur in the circulation process. In the prior art, aiming at the defects of polyaniline conductive materials, the following strategies are mainly adopted for modification: (1) composite modification: by carrying out composite modification on polyaniline and other materials (such as carbon nano tubes and metal oxide nano particles), the conductivity, stability and mechanical property of the conductive material can be improved. (2) nanocrystallization reduces material agglomeration. (3) modification of molecular chain: by regulating and controlling the molecular structure of polyaniline, such as introducing conjugated structure, organic semiconductor micromolecules and the like, the photoelectric conversion efficiency, photosensitivity and luminescence performance of the polyaniline conductive material can be improved, and the application potential of the polyaniline conductive material in the field of photoelectric devices is expanded.
Disclosure of Invention
According to the defects in the prior art of the polyaniline conductive material, the invention provides a modification strategy which takes molecular chain modification and doping modification into consideration, and the modified polyaniline plastic with good processability, circulation stability, mechanical property and high conductivity is obtained.
The invention provides a modified polyaniline conductive plastic, which comprises the following components: aniline polymer, proton acid and metal salt.
As a further improvement of the invention, the polyaniline conductive plastic also comprises PE resin, talcum powder and polyethylene wax.
The aniline polymer has the following structural formula:
wherein R isThe value of x is 0-20, and the value of y is 0-10.
The protonic acid is selected from carboxylic acids such as oxalic acid and acetic acid.
The metal salt is selected from one or more of transition metal water-soluble salts such as cobalt nitrate, ferric chloride, manganese chloride, lithium chloride, cupric chloride and cupric nitrate.
The invention provides a preparation method of an aniline polymer, which comprises the following steps: dissolving terephthalaldehyde in absolute ethanol, adding acid to adjust the pH to 4.5-7, heating to 60-90 ℃, dropwise adding diamine compound solution into a solution system, and carrying out heat preservation reflux reaction for 12-20 h to obtain the aniline polymer.
The acid is selected from glacial acetic acid and hydrochloric acid.
The diamine compound is selected from one or more of 2, 5-diaminopyridine, terephthalic acid dihydrazide and p-phenylenediamine.
The molar ratio of terephthalaldehyde to diamine compound is 1:1.5.
The invention provides a preparation method of polyaniline conductive plastic, which comprises the following steps: (1) Mixing aniline polymer, protonic acid and metal salt in deionized water, then filling into a stainless steel reaction kettle with a polytetrafluoroethylene lining for hydrothermal reaction, specifically heating to 60-120 ℃ for reaction for 2 days, and drying to obtain a metal complex of the aniline polymer; (2) Heating and melting metal complex of aniline polymer, PE resin and polyethylene wax, adding talcum powder, mixing for 2-4 h, extruding and granulating to obtain the conductive plastic.
Preferably, the polyaniline conductive plastic provided by the invention comprises the following components in parts by weight: 50-70 parts of aniline polymer, 10-20 parts of oxalic acid, 5-20 parts of metal salt, 70-120 parts of PE resin, 1-2 parts of talcum powder and 10-15 parts of polyethylene wax.
The complex of the aniline polymer and the metal can be prepared into powder and film materials, and can be modified on other carbon materials such as graphene, carbon cloth, carbon nano tubes, carbon nano fibers and the like by a deposition method.
The invention has the following advantages and beneficial effects:
the aniline polymer provided by the invention has conjugated large pi bond, so that electrons can move in a large area in a delocalization way, and a precondition is provided for conductivity. Further, the aniline polymer reacts with oxalic acid and metal ion brine to form a complex, and the complex has excellent conductivity; in addition, the coordination structure enables the material to have a mesoporous structure, so that the structural stability of the complex is greatly improved, and the cycle performance is improved.
Drawings
Fig. 1 is an infrared spectrogram of example 2 and example 3.
FIG. 2 is an ultraviolet absorption spectrum of example 2 and example 5.
FIG. 3 is an ultraviolet absorption spectrum of example 3 and example 6.
Fig. 4 is a scanning electron microscope image of examples 2,5 and comparative example 2.
FIG. 5 is the CV curves of examples 2,5 and comparative example 4.
Detailed Description
The present invention will be described in further detail with reference to the following examples, which are not intended to limit the invention in any way. Unless specifically stated otherwise, the reagents, methods and apparatus employed in the present invention are those conventional in the art.
Example 1
Preparation of Aniline Polymer 1
Weighing terephthalaldehyde, dissolving in absolute ethanol, adding into a reaction kettle, adding a 4A molecular sieve (sodium-A molecular sieve, the adding amount of which is 0.2 times of the mass of terephthalaldehyde) and hydrochloric acid to adjust pH=5.8, heating to 60 ℃, opening condensation reflux, starting dropwise adding an ethanol solution of a diamine compound, heating to 80 ℃, reacting for 20 hours, filtering while the solution is hot, concentrating the filtrate, re-crystallizing with DMF, and drying to obtain the aniline polymer.
The feeding mole ratio of the terephthalaldehyde to the p-phenylenediamine to the 2, 5-diaminopyridine is 1:1.05:0.45.
example 2
Preparation of Aniline Polymer 2
Weighing terephthalaldehyde, dissolving in absolute ethanol, adding into a reaction kettle, adding a 4A molecular sieve (sodium-A molecular sieve, the adding amount of which is 0.2 times of the mass of terephthalaldehyde) and hydrochloric acid to adjust pH=5.2, heating to 60 ℃, opening condensation reflux, starting dropwise adding an ethanol solution of a diamine compound, heating to 80 ℃, reacting for 20 hours, filtering while the solution is hot, concentrating the filtrate, re-crystallizing with DMF, and drying to obtain the aniline polymer.
The molar ratio of paraphthalaldehyde to p-phenylenediamine to 2, 5-diaminopyridine is 1:0.75:0.75.
Example 3
Preparation of Aniline Polymer 3
Weighing terephthalaldehyde, dissolving in absolute ethanol, adding into a reaction kettle, adding a 4A molecular sieve (sodium-A molecular sieve, the adding amount of which is 0.2 times of the mass of terephthalaldehyde) and glacial acetic acid, regulating pH=6.2, heating to 60 ℃, opening condensation reflux, starting dropwise adding an ethanol solution of a diamine compound, heating to 80 ℃, reacting for 12 hours, filtering while the mixture is hot, concentrating filtrate, re-crystallizing with DMF, and drying to obtain the aniline polymer.
The feeding mole ratio of the terephthalaldehyde to the p-phenylenediamine to the terephthalic acid dihydrazide is 1:1:0.5.
Comparative example 1
Weighing terephthalaldehyde, dissolving in absolute ethanol, adding into a reaction kettle, adding a 4A molecular sieve (sodium-A molecular sieve, the adding amount of which is 0.2 times of the mass of terephthalaldehyde) and glacial acetic acid to regulate pH=6.5, heating to 60 ℃, opening condensation reflux, starting to dropwise add an ethanol solution of p-phenylenediamine, heating to 80 ℃, reacting for 12 hours, filtering while the solution is hot, concentrating the filtrate, re-crystallizing with DMF, and drying to obtain the aniline polymer.
The feeding mole ratio of the terephthalaldehyde to the p-phenylenediamine is 1:1.5.
Comparative example 2
And preparing polyaniline by an electrochemical method.
250ml of 0.2M aniline and 1M H were prepared beforehand in a volumetric flask 2 SO 4 The solution is taken as electrolyte solution, a proper amount of the electrolyte solution is taken in a small beaker, a weighed carbon paper is taken as a working electrode, a Saturated Calomel Electrode (SCE) is taken as a reference electrode, a platinum wire electrode is taken as a counter electrode, a three-electrode system is formed, a cyclic voltammetry technology is selected on a CHI660d electrochemical workstation, the working voltage range is-0.2-1.25V (vs SCE), and the scanning rate is 50mV s -1 The aniline monomer is polymerized at room temperature to generate a product which is deposited on a working electrode, the electrode is taken out, washed by distilled water, dried in vacuum for 24 hours to constant weight at 80 ℃, and the required powder is scraped from the working electrode.
The polymers prepared in examples 1 to 3 and comparative example 1 above were doped with a metal salt and a protonic acid.
The polymer powder, protonic acid and metal salt are weighed according to the feeding ratio and mixed in deionized water, then the mixture is put into a stainless steel reaction kettle with a polytetrafluoroethylene lining, the temperature is raised to 100 ℃ for hydrothermal reaction for 2d, and the mixture is kept stand and cooled to obtain complex crystals, wherein the formula of the complex is shown in table 1.
TABLE 1
Test example 1 gel chromatography (GPC)
The test was performed using a GPC tester model TDA305MAX manufactured by ATI corporation, U.S.A., with NMP phase as the mobile phase and 0.5mL/min flow rate, 100. Mu.L sample intake volume, and 50 ℃.
TABLE 2
Project Example 1 Example 2 Example 3 Comparative example 1
Mn 2868 2864 4010 3843.675
Mw 5190 6473 8903 6419
PDI 1.81 2.26 2.22 1.67
Test example 2FT-IR Spectroscopy
The test shows that the proper amount of aniline polymer powder and KBr tablet are fully ground in an agate mortar to obtain a uniformly mixed powder tablet, and the result is shown in figure 1.
Test example 3 ultraviolet absorption Spectrum
The aniline polymer and its complex were tested for ultraviolet absorption spectrum in 200 to 400nm using DMF as solvent and an ultraviolet-visible spectrophotometer (Shimadzu, UV-2600), and the results are shown in FIGS. 2 and 3.
In the figure, 226nm or 269nm corresponds to benzene ring pi-pi electron transition; 334nm or 327nm is the n-pi electron transition of the imino group; 291nm corresponds to a pyridine pi-pi electron transition.
Test example 4 Scanning Electron Microscope (SEM)
A small amount of the complex/polyaniline powder to be measured was taken and subjected to ultrasonic dispersion in a proper amount of pure ethanol solution, a small amount of the mixed dispersion was sucked by a dropper and was dripped onto a square copper sheet having a size of 1cm×1cm, and after drying at 80 ℃, the morphology and structure of the sample were observed under SEM (FEI company, nova400 NanoSEM, usa) and the results are shown in fig. 4.
Test example 5 electrochemical Performance test
(1) Resistivity test
The four-probe instrument is adopted for testing, aniline polymer or the complex powder thereof is pressed into a sheet with the thickness of 1-2 mm on a proper grinding tool, the needle tips of the four probes simultaneously contact the sheet during testing, the two probes on the outer side are connected to a constant current source, and the two probes on the inner side are connected with a voltmeter. The conductivity of the sheet was calculated by the following formula:
wherein d is the thickness of the sheet, cm; i is the current flowing through the sheet, A; v is the voltage across the foil, V.
TABLE 3 Table 3
(2) Cyclic voltammetry test (CV)
Preparation of aniline polymer electrode: the mass of the aniline polymer or the complex powder thereof is as follows: acetylene black fine powder: PTFE emulsion=90:5:5, weighing a proper amount of aniline polymer complex and acetylene black fine powder, adding into a mortar, then dripping a proper amount of absolute ethyl alcohol, and starting grinding to enable the aniline polymer complex and the acetylene black fine powder to be mixed more finely and uniformly; and (3) dropwise adding PTFE emulsion serving as a binder into a mortar in proportion, continuously grinding until the mixture in the mortar is pasty, coating the mixture on a dried and weighed carbon paper working electrode, and drying the mixture in a vacuum drying oven at 80 ℃ for 24 hours to constant weight.
Test conditions: in a three-electrode system, the scanning voltage ranges from-0.2V to 0.6V, the scanning speed is 5mV/s, and the result is shown in figure 5.
(3) Cycle performance test
The electrode material prepared by the method is 5A g -1 1000 cycle life tests were performed, and the cycle stability of the materials was evaluated with the capacity retention rates of the three electrodes, and the results are shown in Table 4.
TABLE 4 Table 4
Plastics of different formulations were prepared and are listed in Table 3.
Heating and melting the complex powder of the aniline polymer, PE resin and polyethylene wax, adding talcum powder, mixing for 2-4 h, extruding and granulating to obtain the conductive plastic.
PE resin, brand PE-L M2750, available from China petrochemical Co., ltd; polyethylene wax, trademark HoneywellA-C540A, available from Shanghai Zhen Li Ji Gao Techno Co., ltd
TABLE 3 Table 3
Test example 6
(1) Resistivity: tested according to the method of ISO 3915;
(2) Tensile strength and elongation at break: testing according to the method of GB/T1040.2-2022; the sample sizes were 130mm by 6mm by 3mm.
(3) Limiting oxygen index: tested according to the method of GB/T2406-1993.
The test results are shown in Table 4.
TABLE 4 Table 4
The above is a further detailed description of the invention in connection with specific preferred embodiments, and it is not to be construed as limiting the practice of the invention to these descriptions. It will be apparent to those skilled in the art that several simple deductions or substitutions may be made without departing from the spirit of the invention, and these shall be considered to be within the scope of the invention.

Claims (6)

1. The modified polyaniline conductive plastic is characterized by comprising the following components in parts by weight: 50-70 parts of aniline polymer, 10-20 parts of carboxylic acid protonic acid, 5-20 parts of metal salt, 70-120 parts of PE resin, 1-2 parts of talcum powder and 10-15 parts of polyethylene wax; the preparation method of the aniline polymer comprises the following steps: dissolving terephthalaldehyde in absolute ethanol, adding a molecular sieve and acid to adjust the pH value to 4.5-7, heating to 60-90 ℃, dropwise adding diamine compound solution into a solution system, and carrying out heat preservation reflux reaction for 12-20 h to obtain an aniline polymer; the diamine compound is p-phenylenediamine and 2, 5-diaminopyridine or terephthalic acid dihydrazide; the metal salt is selected from one or more water soluble salts in Co, mn, fe, cu.
2. The modified polyaniline conductive plastics as described in claim 1, wherein the carboxylic acid protonic acid is selected from oxalic acid and acetic acid.
3. The modified polyaniline conductive plastics as described in claim 1, wherein the metal salt is selected from one or more of cobalt nitrate, ferric chloride, manganese chloride, cupric chloride, and cupric nitrate.
4. The modified polyaniline conductive plastics as described in claim 1, wherein the acid is one selected from glacial acetic acid and hydrochloric acid.
5. The modified polyaniline conductive plastic according to claim 1, wherein the molar ratio of terephthalaldehyde to diamine compound is 1:1.5.
6. The method for preparing the modified polyaniline conductive plastic according to claim 1, comprising the steps of: (1) Mixing aniline polymer, protonic acid and metal salt in deionized water, then filling into a stainless steel reaction kettle with a polytetrafluoroethylene lining for hydrothermal reaction, specifically heating to 60-120 ℃ for reaction for 2 days, and drying to obtain a metal complex of the aniline polymer; (2) Heating and melting metal complex of aniline polymer, PE resin and polyethylene wax, adding talcum powder, mixing for 2-4 h, extruding and granulating to obtain the conductive plastic.
CN202311080367.4A 2023-08-25 2023-08-25 Modified polyaniline conductive plastic and preparation method thereof Pending CN116874916A (en)

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20180019156A1 (en) * 2016-07-15 2018-01-18 Brewer Science Inc. Laser ablative dielectric material

Patent Citations (1)

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Publication number Priority date Publication date Assignee Title
US20180019156A1 (en) * 2016-07-15 2018-01-18 Brewer Science Inc. Laser ablative dielectric material

Non-Patent Citations (3)

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Title
尤玲丽: "共轭聚席夫碱及其盐的合成及性能研究", 中国优秀硕士学位论文全文数据库（工程科技Ⅰ辑）, no. 2018, pages 12 - 29 *
徐桠楠: "聚席夫碱的合成与表征", 天津理工大学学报, vol. 26, no. 3, pages 40 - 42 *
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