CN111704718B - Preparation method of polyimide electrode material with multilevel structure - Google Patents
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- 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
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
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Abstract
The invention relates to a preparation method of a polyimide electrode material with a multilevel structure, which comprises the following steps: (1) adding diamine and dianhydride monomers with equal mol into a solvent, stirring at room temperature under the protection of nitrogen to react to obtain a polyamic acid solution, and then adding a dehydrating cyclization agent to cause the polyamic acid to be subjected to partial chemical imidization; (2) transferring the partially cyclized polyamic acid solution into a high-pressure reaction kettle, and after high-temperature reaction, cooling, filtering, washing and vacuum drying to obtain powder; and (3) placing the polyimide electrode material in an inert atmosphere for heat treatment to obtain the polyimide electrode material with the multilevel structure. The method combines chemical pre-cyclization and solvent heat treatment to form a multi-stage structure to increase the specific surface area of the polyimide electrode material, so that the utilization efficiency of active sites is improved, and the method has great industrialization potential.
Description
Technical Field
The invention belongs to the field of organic electrode materials, and particularly relates to a preparation method of a polyimide electrode material with a multilevel structure.
Background
The negative electrode material of the current lithium ion battery is mainly a graphite carbon material, however, due to the limitation of capacity, the graphite negative electrode has difficulty in meeting the requirements of high-power equipment. In order to break the limitation of graphite negative electrodes, development of novel negative electrode materials is imperative. At present, the research directions of the cathode materials mainly include metal oxide cathodes, silicon cathodes, organic compound cathode materials and the like. Among various negative electrode materials, the organic conjugated carbonyl compound has become a hotspot of current research in the field of energy storage by virtue of the advantages of structural diversity, environmental friendliness, high theoretical specific capacity and the likeOne of them. The organic conjugated carbonyl compound and the graphite structure both contain aromatic C6 rings, except that the C6 ring can only be inserted with one lithium in the discharge process of the graphite cathode, so the theoretical capacity is not high (372mAh/g), and the aromatic C6 ring of the conjugated carbonyl compound can realize the superlithiation under the low discharge potential (1.0V-0.01V), so that Li is formed6/C6The theoretical specific capacity of the addition complex is generally over 1500mAh/g, and the addition complex has great potential as a negative electrode material of a lithium ion battery.
Polyimide is taken as a typical organic conjugated carbonyl compound, has high theoretical specific capacity, has the advantages of high thermal stability, stable electrochemical structure, fast reaction kinetics, various structures and the like, and is expected to become a lithium ion battery cathode material with application prospect. However, the macromolecular structure chain of the polymer is easy to fold and bend, so that the polymer is subjected to an agglomeration phenomenon on a macroscopic scale. Only the active sites on the surface of the polymer which is closely packed are exposed, and the actual specific capacity is far less than the theoretical capacity. Patent CN106129412A reports a high molecular weight polyimide as a negative electrode material of a lithium ion battery, but it only relies on electrochemical oxidation-reduction of acyl groups in the polyimide molecule to realize energy storage, so the specific capacity is lower than 250 mAh/g. Therefore, a new method for adjusting the morphology structure of the polymer and improving the actual specific capacity needs to be developed.
Disclosure of Invention
The technical problem to be solved by the invention is to provide a preparation method of a polyimide electrode material with a multilevel structure, which adjusts the morphological structure of a polymer by adopting a method of combining chemical pre-cyclization and solvent heat treatment, increases the specific surface area of the polymer and further improves the utilization rate of active sites.
The invention provides a preparation method of a polyimide electrode material with a multilevel structure, which comprises the following steps:
(1) under the protection of inert atmosphere, sequentially adding equimolar diamine monomer and dianhydride monomer into a solvent according to the mass concentration of 7.4-92.6mg/ml, stirring and reacting at room temperature for 6-12h to obtain polyamic acid solution, then adding a chemical cyclization reagent, and continuously stirring for 4-8h to obtain partially cyclized polyamic acid solution;
(2) transferring the partially cyclized polyamic acid solution into a high-pressure reaction kettle, reacting for 2-24h at 150-210 ℃, cooling, filtering, washing, and drying in vacuum to obtain powder; and (3) placing the polyimide electrode material in an inert atmosphere for heat treatment to obtain the polyimide electrode material with a multilevel structure.
The diamine monomer in the step (1) is one or more of p-phenylenediamine PDA, biphenyldiamine BDA, diaminodiphenyl ether ODA, p-aminoanthraquinone DAAQ and benzoquinonyl-containing diamine AQPDA. The structural formula is as follows:
the dianhydride monomer in the step (1) is one or more of 1,2,4, 5-pyromellitic dianhydride PMDA, 3,3,4, 4-benzophenonetetracarboxylic dianhydride BTDA and 2,3,3 ', 4' -biphenyl tetracarboxylic dianhydride BPDA. The structural formula is as follows:
the solvent in the step (1) is one or more of N-methylpyrrolidone NMP, N-dimethylformamide DMF and dimethylacetamide DMAc.
The chemical cyclization reagent in the step (1) is a pyridine/acetic anhydride mixed solution with a molar ratio of 1: 1; the volume ratio of the chemical cyclization reagent to the solvent is 1-2: 25-30.
The vacuum drying in the step (2) comprises the following process parameters: the vacuum drying temperature is 60-85 ℃, and the vacuum drying time is 12-24 h.
The technological parameters of the heat treatment in the step (2) are as follows: the heat treatment temperature is 300-600 ℃, and the heat treatment time is 2-10 h; the inert atmosphere is nitrogen or argon.
The polyimide electrode material with the multilevel structure obtained in the step (2) is used as a negative electrode material of a lithium ion battery. Coating the polyimide electrode material with multilevel structure mixed with Ketjen black and vinylidene chloride on a copper foilRolling into negative plate; the counter electrode adopts a lithium metal sheet, the diaphragm adopts a PP/PET composite material, and the electrolyte is LiPF6The ester solution is assembled into a lithium ion battery, and the specific capacity is 650-1480 mAh/g.
Advantageous effects
(1) Compared with the polyimide electrode material polymerized by a one-step high-temperature method, the polyimide electrode material prepared by the method combining chemical pre-cyclization and solvent heat treatment has an obvious multi-level morphology structure, and the larger specific surface area of the polyimide electrode material can expose more active sites, so that the actual specific capacity is improved.
(2) The specific capacity of a lithium ion battery formed by assembling the polyimide electrode material prepared by the invention as a lithium ion battery cathode material can reach 650-1480 mAh/g, and the polyimide electrode material has the electrochemical characteristics of high multiplying power and high cycling stability.
Drawings
Fig. 1 is an SEM image of the polyimide electrode material having a multilevel structure obtained in example 1.
Detailed Description
The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. Further, it should be understood that various changes or modifications of the present invention may be made by those skilled in the art after reading the teaching of the present invention, and such equivalents may fall within the scope of the present invention as defined in the appended claims.
Example 1
(1) 20ml of NMP is put into a 100ml three-neck flask, and nitrogen is introduced for protection to prevent water vapor from entering a solvent. 320mg of AQPDA and 218mg of 1,2,4, 5-pyromellitic dianhydride (PMDA) are sequentially added into a three-neck flask, and stirred and reacted for 8 hours at room temperature to obtain a polyamic acid solution. 1ml of pyridine/acetic anhydride mixed solution is added dropwise into a three-neck flask, and stirring is continued for 4 hours to obtain a partially cyclized polyamic acid solution.
(2) Transferring the partially cyclized polyamic acid solution into a 50ml high-pressure reaction kettle, putting the reaction kettle into a vacuum drying oven at 180 ℃ for reaction for 2 hours, cooling, filtering, washing, and vacuum drying at 80 ℃ for 12 hours to obtain brown yellow powder; and then placing the polyimide electrode material in nitrogen for heat treatment at 300 ℃ for 6h to obtain the polyimide electrode material with the multilevel structure.
The polyimide electrode material with the multilevel structure obtained in the embodiment is used as a negative electrode material of a lithium ion battery, mixed Ketjen black and vinylidene chloride are coated on a copper foil, and the copper foil is rolled into a negative electrode sheet; the counter electrode adopts a lithium metal sheet, the diaphragm adopts a PP/PET composite material, and the electrolyte is LiPF6The ester solution is assembled into a lithium ion battery, and the specific capacity is 1480 mAh/g. As can be seen from fig. 1, the polyimide electrode material having a multi-level structure obtained in this example has a distinct multi-layer sheet structure.
Example 2
(1) 50ml of DMF was placed in a 100ml three-necked flask and protected with nitrogen to prevent the ingress of water vapor into the solvent. 1191mg of p-aminoanthraquinone (DAAQ) and 1611mg of 3,3,4, 4-benzophenonetetracarboxylic dianhydride (BTDA) were sequentially added to a three-necked flask, and stirred at room temperature for 12 hours to obtain a polyamic acid solution. 2ml of pyridine/acetic anhydride mixed solution is added dropwise into the three-necked flask, and stirring is continued for 6 hours to obtain a partially cyclized polyamic acid solution.
(2) Transferring the partially cyclized polyamic acid solution into a 100ml high-pressure reaction kettle, putting the reaction kettle into a vacuum drying oven at 180 ℃ for reaction for 10 hours, cooling, filtering, washing, and vacuum drying at 80 ℃ for 12 hours to obtain dark yellow powder; and then placing the polyimide electrode material in nitrogen for heat treatment at 400 ℃ for 8h to obtain the polyimide electrode material with the multilevel structure.
The polyimide electrode material with the multilevel structure obtained in the embodiment is used as a negative electrode material of a lithium ion battery, mixed Ketjen black and vinylidene chloride are coated on a copper foil, and the copper foil is rolled into a negative electrode sheet; the counter electrode adopts a lithium metal sheet, the diaphragm adopts a PP/PET composite material, and the electrolyte is LiPF6The ester solution is assembled into the lithium ion battery, and the specific capacity is 1322 mAh/g.
Example 3
(1) 30ml of DMF was placed in a 100ml three-necked flask and protected with nitrogen to prevent water vapor from entering the solvent. 270mg of p-Phenylenediamine (PDA) and 545mg of 1,2,4, 5-pyromellitic dianhydride (PMDA) are sequentially added into a three-neck flask, and stirred and reacted for 8 hours at room temperature to obtain a polyamic acid solution. 1ml of pyridine/acetic anhydride mixed solution is added dropwise into a three-neck flask, and stirring is continued for 4 hours to obtain a partially cyclized polyamic acid solution.
(2) Transferring the partially cyclized polyamic acid solution into a 50ml high-pressure reaction kettle, putting the reaction kettle into a vacuum drying oven at the temperature of 210 ℃ for reaction for 12 hours, cooling, filtering and washing the reaction kettle, and performing vacuum drying at the temperature of 80 ℃ for 12 hours to obtain brown yellow powder; and then placing the polyimide electrode material in nitrogen for heat treatment at 300 ℃ for 8h to obtain the polyimide electrode material with the multilevel structure.
The polyimide electrode material with the multilevel structure obtained in the embodiment is used as a negative electrode material of a lithium ion battery, mixed Ketjen black and vinylidene chloride are coated on a copper foil, and the copper foil is rolled into a negative electrode sheet; the counter electrode adopts a lithium metal sheet, the diaphragm adopts a PP/PET composite material, and the electrolyte is LiPF6The ester solution is assembled into a lithium ion battery, and the specific capacity is 680 mAh/g.
Example 4
(1) 50ml of DMF was placed in a 100ml three-necked flask and protected with nitrogen to prevent the ingress of water vapor into the solvent. 920mg of Biphenyldiamine (BDA) and 1470mg of 1,2,4, 5-pyromellitic dianhydride (PMDA) are sequentially added into a three-neck flask, and stirred and reacted for 8 hours at room temperature to obtain a polyamic acid solution. 2ml of pyridine/acetic anhydride mixed solution is added dropwise into a three-neck flask, and stirring is continued for 8 hours to obtain a partially cyclized polyamic acid solution.
(2) Transferring the partially cyclized polyamic acid solution into a 50ml high-pressure reaction kettle, putting the reaction kettle into a 180 ℃ vacuum drying oven for reaction for 12 hours, cooling, filtering and washing the reaction kettle, and performing vacuum drying for 12 hours at 80 ℃ to obtain dark brown powder; and then placing the polyimide electrode material in nitrogen for heat treatment at 400 ℃ for 8h to obtain the polyimide electrode material with the multilevel structure.
The polyimide electrode material with the multilevel structure obtained in the embodiment is used as a negative electrode material of a lithium ion battery, mixed Ketjen black and vinylidene chloride are coated on a copper foil, and the copper foil is rolled into a negative electrode sheet; the counter electrode adopts a lithium metal sheet, the diaphragm adopts a PP/PET composite material, and the electrolyte is LiPF6The ester solution is assembled into a lithium ion battery, and the specific capacity is 1284 mAh/g.
Claims (6)
1. A preparation method of a polyimide electrode material with a multilevel structure comprises the following steps:
(1) under the protection of inert atmosphere, sequentially adding equimolar diamine monomer and dianhydride monomer into a solvent according to the total mass concentration of 7.4-92.6mg/ml, stirring and reacting at room temperature for 6-12h to obtain polyamic acid solution, then adding a chemical cyclization reagent, and continuously stirring for 4-8h to obtain partially cyclized polyamic acid solution; wherein the chemical cyclization reagent is pyridine/acetic anhydride mixed solution with the molar ratio of 1: 1; the volume ratio of the chemical cyclization reagent to the solvent is 1-2: 25-30;
(2) transferring the partially cyclized polyamic acid solution into a high-pressure reaction kettle, reacting for 2-24h at 150-210 ℃, cooling, filtering, washing, and drying in vacuum to obtain powder; placing the polyimide electrode material in an inert atmosphere for heat treatment to obtain a polyimide electrode material with a multilevel structure; the polyimide electrode material with the multilevel structure is used as a negative electrode material of a lithium ion battery.
2. The method of claim 1, wherein: the diamine monomer in the step (1) is one or more of p-phenylenediamine PDA, biphenyldiamine BDA, diaminodiphenyl ether ODA, p-aminoanthraquinone DAAQ and 2, 5-bis (1, 4-phenylenediamine) -1, 4-benzoquinone AQPDA.
3. The method of claim 1, wherein: the dianhydride monomer in the step (1) is one or more of 1,2,4, 5-pyromellitic dianhydride PMDA, 3,3 ', 4, 4' -benzophenonetetracarboxylic dianhydride BTDA and 2,3,3 ', 4' -biphenyltetracarboxylic dianhydride BPDA.
4. The method of claim 1, wherein: the solvent in the step (1) is one or more of N-methylpyrrolidone NMP, N-dimethylformamide DMF and dimethylacetamide DMAc.
5. The method of claim 1, wherein: the vacuum drying in the step (2) comprises the following process parameters: the vacuum drying temperature is 60-85 ℃, and the vacuum drying time is 12-24 h.
6. The method of claim 1, wherein: the technological parameters of the heat treatment in the step (2) are as follows: the heat treatment temperature is 300-600 ℃, and the heat treatment time is 2-10 h; the inert atmosphere is nitrogen or argon.
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| CN114927686A (en) * | 2022-05-27 | 2022-08-19 | 哈尔滨工程大学 | Preparation method and application of novel aqueous magnesium-sodium mixed ion battery cathode material |
| CN115197082B (en) * | 2022-05-31 | 2023-09-22 | 上海交通大学 | Anthraquinone diamine monomer, magenta intrinsic polyimide derived from anthraquinone diamine monomer and preparation method of magenta intrinsic polyimide |
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