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Novel free radical monomer containing diphenylamine structure, polymer and preparation method thereof, and preparation method and application of polymer

A free radical and diphenylamine technology, applied in the field of material science, can solve the problems of short cycle time, high price, and flammability, and achieve the effects of improved redox ability, theoretical specific capacity, and easy purification

Active Publication Date: 2020-02-25
WUHAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The positive electrode active materials of traditional lithium-ion batteries usually use transition metal oxides such as LiCoO2, which have low energy density and discharge capacity, difficulty in fast charging and discharging, short cycle time, and high price. Toxic, flammable, explosive, poor battery safety and other disadvantages

Method used

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  • Novel free radical monomer containing diphenylamine structure, polymer and preparation method thereof, and preparation method and application of polymer
  • Novel free radical monomer containing diphenylamine structure, polymer and preparation method thereof, and preparation method and application of polymer
  • Novel free radical monomer containing diphenylamine structure, polymer and preparation method thereof, and preparation method and application of polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Synthesis of poly N1,N1-bis(4-aminophenyl)-N4,N4-diphenylbenzene-1,4-diamine-PROXYL

[0049]

[0050] (1) Synthesis of intermediate 4-nitro-N, N-diphenylaniline:

[0051] Add 4.23g (0.025mol) of diphenylamine, 0.600g (0.025mol) of sodium hydride and 200ml of DMF into a 500ml three-neck flask, and stir at room temperature for 10min. Add 2.65ml (0.025mol) of p-fluoronitrobenzene to react for 15h during the heating process. Pour the reaction solution into ice water, extract with dichloromethane, evaporate the solvent under reduced pressure, and the product is dichloromethane : n-hexane=1:2 (volume ratio) as the mobile phase, silica gel as the stationary phase for column chromatography purification, the product was collected and spin-dried, and dried in vacuum at 80°C for 24h to obtain 5.961g of the product with a yield of 82%. The intermediate structure is as follows:

[0052]

[0053] (2) Synthesis of intermediate N1, N1-diphenylbenzene-1,4-diamine:

[0054] Add ...

Embodiment 2

[0066] Synthesis of poly N1,N1-bis(4-aminophenyl)-N4,N4-diphenylbenzene-1,4-diamin-e-PROXYL

[0067]

[0068] (1) Synthesis of intermediate 5-nitro-N, N-diphenylpyrimidin-2-amine:

[0069] Add 4.230g (0.025mol) of diphenylamine, 0.600g (0.025mol) of sodium hydride and 200ml of DMF into a 500ml three-neck flask, and stir at room temperature for 10min. Then add the temperature to 110 ° C, add 3.570g (0.025mol) 2-fluoro-5-nitropyrimidine during the heating process and react for 15h. The reaction solution is poured into ice water, extracted with dichloromethane, and the solvent is evaporated under reduced pressure to obtain the product Using dichloromethane:n-hexane=1:2.5 (volume ratio) as the mobile phase and silica gel as the stationary phase for column chromatography purification, the product was collected and spin-dried, and dried in vacuum at 80°C for 24h to obtain 6.060g of the product. The yield was 83%. The intermediate structure is as follows:

[0070]

[0071] 2...

Embodiment 3

[0086] Synthesis of poly N1,N1-bis(4-aminophenyl)-N4,N4-diphenylbenzene-1,4-diamin-e-PROXYL

[0087]

[0088] (1) Synthesis of intermediate 4-nitro-N, N-diphenylnaphthalen-1-amine:

[0089] Add 4.230g (0.025mol) of diphenylamine, 0.600g (0.025mol) of sodium hydride and 250ml of DMF into a 500ml three-necked flask, and stir at room temperature for 10min. Then add the temperature to 110 ° C, add 4.775g (0.025mol) 1-fluoro-4-nitronaphthalene during the heating process and react for 15h. The reaction solution is poured into ice water, extracted with dichloromethane, and the solvent is evaporated under reduced pressure, the product Using dichloromethane:n-hexane=1:2.5 (volume ratio) as the mobile phase and silica gel as the stationary phase for column chromatography purification, the product was collected and spin-dried, and dried in vacuum at 80°C for 24h to obtain 6.800g of the product. The yield was 80%. The intermediate structure is as follows:

[0090]

[0091] 2) Syn...

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Abstract

The invention discloses a novel free radical monomer containing a diphenylamine structure, a polymer and a preparation method thereof, and a preparation method and an application of the polymer. Diphenylamine is used as a raw material to prepare the novel free radical material containing the diphenylamine structure; and the synthesis method of the free radical monomer has the advantages of simpleprocess, high yield, easiness in purification, and suitableness for industrial production. The obtained free radical compound monomer is dissolved in chloroform, anhydrous ferric trichloride with themole being 2-5 times that of the monomer is added as an oxidant, and an oxidative polymerization reaction is carried out in a protective atmosphere to prepare the free radical polymer containing the polydiphenylamine skeleton. The main chain of the polymer has good conductivity, the polymer has better rate capability and cycling stability than other free radical polymer materials, and the theoretical specific capacity of a free radical polymer battery is greatly higher than that of other free radical polymers of a single electron reaction.

Description

technical field [0001] The invention relates to the field of material science, in particular to a novel radical monomer containing a diphenylamine structure and a polymer preparation method thereof. The monomer can be used to synthesize polymers such as functionalized polydiphenylamine, and particularly relates to the preparation and application of a free radical polymer battery material. Background technique [0002] As an important energy storage device, lithium-ion batteries have been widely used in portable consumer electronics, electric vehicles, and hybrid electric vehicles. The growing application of energy storage not only requires electrochemical batteries to have sufficient energy density, but also their price As well as material sustainability and environmental hazards put forward certain requirements. The positive electrode active materials of traditional lithium-ion batteries usually use transition metal oxides such as LiCoO2, which have low energy density and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01M4/60H01M10/0525
CPCC08G61/12C08G2261/11C08G2261/1432C08G2261/1434C08G2261/3162H01M4/602H01M10/0525Y02E60/10
Inventor 董丽杰熊宇风袁野欧颖张扬琚艳云
Owner WUHAN UNIV OF TECH
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