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Multi-cyandiamine monomer and preparation and application thereof

The technology of polycyanodiamine monomer and polycyanopolyimide is applied in the fields of polycyanodiamine-containing monomer and its preparation and application, and can solve the problem of separation of material and matrix, poor adsorption performance, sulfonation high degree issues

Inactive Publication Date: 2013-07-10
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the reported polyimide materials, although the polyimide polymer used as the coating material has excellent thermal stability and mechanical properties, its adsorption performance with the coated substrate is poor, Causes material to separate from matrix in application
However, when polyimide polymer is used as the proton exchange membrane, the sulfonation of the material is too high due to the pursuit of high proton conductivity, so that the water absorption rate of the material is too high at high temperature, and the dimensional stability is greatly reduced.

Method used

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  • Multi-cyandiamine monomer and preparation and application thereof
  • Multi-cyandiamine monomer and preparation and application thereof
  • Multi-cyandiamine monomer and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] (1) Add 3.168g (0.015mol) of 4-cyanophenylhydroquinone, 2-chloro-5-nitrobenzene to a three-necked flask equipped with an electric stirring device, nitrogen protection device and water dispenser Nitrile 5.751g (0.0315mol) and anhydrous potassium carbonate 2.346g (0.017mol), 45mL (43g) DMF and 15mL toluene, stirred and reacted at 132-135°C for 2-3 hours, after the water was completely removed, the water and toluene were released ; Heating to 148-152°C and continuing to stir for 3-4 hours; Pour the reactant into a mixture of ice water and ethanol to obtain a large amount of yellow precipitate; After filtering, wash with pure water several times, and dry the product in vacuum at 80°C to obtain polycyanide Dinitromonomer 2,5-bis(4-nitro-2-cyanophenoxy)-1-benzonitrile, i.e. tricyanodinitromonomer, the yield is 90%~95% ;

[0067] (2) Add the 2,5-bis(4-nitro-2-cyanophenoxy)-1-benzene Formaldehyde 5.03g (0.01mol), 0.2g of 10% palladium carbon catalyst and 100mL of absolute eth...

Embodiment 2

[0071] Change the consumption of reactant, repeat embodiment 1. The consumption of all reactants is 2 times of implementing 1.

[0072] The characterization results of tricyanodinitro monomer and tricyanodiamine monomer are similar to those in Example 1.

Embodiment 3

[0074] Repeat Example 2 with 7.087g (0.03mol) 3,4-2 cyanophenyl hydroquinone instead of 4-cyanophenyl hydroquinone to synthesize tetracyanodiamine monomer 2,5-di( 4-Amino-2-cyanophenoxy)-1-o-dibenzonitrile, in step (2), the intermediate polycyanodinitromonomer 2,5-bis(4-nitro-2 -cyanophenoxy)-1-o-dibenzonitrile (abbreviated as tetracyanodinitromonomer) 10.56g; the tetracyanodiamine monomer 2,5-bis(4-amino-2 -cyanophenoxy)-1-o-dibenzonitrile (i.e. tetracyanodiamine monomer) has a melting point of 236°C and a yield of 82%; its structural formula is as follows:

[0075]

[0076] From Figure 4 It can be seen that the infrared characteristic peaks of tetracyanodinitro monomer and tetracyanodiamine monomer are similar to the tricyano monomer in Example 1, which proves that the present invention has prepared tetracyanodiamine monomer.

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Abstract

The invention relates to a multi-cyandiamine monomer and preparation and application thereof, and belongs to the technical field of polymer materials and synthesis thereof. The multi-cyandiamine monomer includes tricyandiamine monomers and tetrocyandiamine monomers. The multi-cyandiamine monomer is polymerized with anhydride to obtain polyimide. Various multi-cyanpolyimide polymers are obtained by chemistry ring-closure and heat ring-closure methods. The polyimide polymer is dissolved in a solvent and a plate coating method is used for paving a film to obtain a desired polyimide film material. The multi-cyanpolyimide material of the invention possesses high thermal stability, excellent film-forming property and excellent adsorbability and dimension stability caused by microscopic intermolecular interaction. The cyan can also be introduced to a sulfonate polyimide material to enhance intermolecular forces between main chains, reduce a swelling coefficient of the sulfonate polyimide material, and enhance dimension stability of the film material which can be used as a proton conduction film material for a fuel cell.

Description

technical field [0001] The invention belongs to the technical field of polymer materials and their synthesis, and specifically relates to various polycyanodiamine-containing monomers and their preparation and application. Background technique [0002] Polyimide is a kind of heat-resistant polymer material with excellent comprehensive performance. It has the advantages of high heat resistance, high mechanical performance and chemical stability, excellent film-forming performance and low dielectric constant. It is widely used in aerospace industry and Microelectronics industry and other fields. [0003] In the main chain of polyimide, a large number of cyano groups are introduced in the form of diamine monomers. Because the cyano group has a large dipole moment and strong polarity, it is easy to form hydrogen bonds and strong bonds with other groups. The intermolecular force increases the polarity of the polymer material. When used as a coating material, it can form an obviou...

Claims

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Application Information

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IPC IPC(8): C07C255/59C07C253/30C07C315/04C07C317/22C08G73/10
Inventor 刘佰军宋洋金银花姜振华
Owner JILIN UNIV
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