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Aromatic diamine containing imidazolyl and preparation method thereof

A technology containing imidazole-based aromatic diamines and aromatic tetramines, which is applied in organic chemistry and other fields, can solve the problems of few types of imidazole-based diamine-containing monomers and limit the development of imidazole-based polymer varieties, and achieve rich types, Effects of improved performance and broad application prospects

Inactive Publication Date: 2011-09-14
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Polyimide containing imidazole group is usually formed by polycondensation of dibasic acid anhydride and diamine monomer containing imidazole group, and polyamide containing imidazole group can be formed by polycondensation of aromatic dibasic anhydride and diamine monomer containing imidazole group. Imidazole-based diamine is the key monomer raw material for the preparation of these two types of materials, but so far, there are very few types of imidazole-based diamine-containing monomers, which limits the development of imidazole-based polymer varieties

Method used

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  • Aromatic diamine containing imidazolyl and preparation method thereof
  • Aromatic diamine containing imidazolyl and preparation method thereof
  • Aromatic diamine containing imidazolyl and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] In a 100mL dry three-necked flask, add 100g of polyphosphoric acid with a mass concentration (calculated as phosphorus pentoxide) of 86%, 5.486g (40mmol) of 4-aminobenzoic acid and 4.2854g (20mmol) of 3,3'- Diaminobenzidine. Under the protection of nitrogen, the temperature was raised to 150 ° C, and after 2 hours of reaction, the temperature was raised to 190 ° C, and the reaction was completed for 20 hours. The product was poured into crushed ice to obtain a light yellow solid, which was fully washed with 0.1M sodium bicarbonate solution. Remove residual phosphoric acid in the solid, then wash with deionized water until neutral, and dry in vacuum at 60°C. The yield is about 85%.

[0031] Spectroscopic characterization of the as-prepared product was carried out. figure 1 It is the nuclear magnetic resonance spectrum of 2,2'-bis(4-aminophenyl)-5,5'-bibenzimidazole (solvent: DMSO-d 6 ), the attribution of each peak is marked in the spectrum respectively: δ=12.4ppm (b,...

Embodiment 2

[0034] In a 100mL dry three-necked flask, add 100g of polyphosphoric acid with a mass concentration (calculated as phosphorus pentoxide) of 86%, 10.972g (80mmol) of 4-aminobenzoic acid and 4.2854g (20mmol) of 3,3'- Diaminobenzidine. Under the protection of nitrogen, the temperature was raised to 150°C, and after 2 hours of reaction, the temperature was raised to 190°C, and the reaction was completed for 20 hours. The product was poured into crushed ice to obtain a light yellow solid, which was fully washed with 0.1M sodium hydroxide solution. Remove residual phosphoric acid in the solid, then wash with deionized water until neutral, and dry in vacuum at 60°C. The yield is about 87%.

[0035] The prepared product has been carried out spectroscopic characterization, and the nuclear magnetic resonance spectrogram and infrared spectrum that record are identical with embodiment 1 ( figure 1 with 2 ).

Embodiment 3

[0037]In a 100mL dry three-necked flask, add 100g of polyphosphoric acid with a mass concentration (calculated as phosphorus pentoxide) of 86%, 5.486g (40mmol) of 3-aminobenzoic acid and 4.2854g (20mmol) of 3,3'- Diaminobenzidine. Under the protection of nitrogen, the temperature was raised to 140°C, and after 3 hours of reaction, the temperature was raised to 190°C, and the reaction was completed for 20 hours. After the reaction was completed, the product was poured into crushed ice to obtain a light yellow solid, which was placed in 1M ammonia water, stirred and washed thoroughly. Remove residual phosphoric acid in the solid, then wash with deionized water until neutral, and dry in vacuum at 60°C. The yield is about 80%.

[0038] Spectroscopic characterization of the as-prepared product was carried out. image 3 It is the nuclear magnetic resonance spectrum of 2,2'-bis(3-aminophenyl)-5,5'-bibenzimidazole (solvent: DMSO-d 6 ), the attribution of each peak is marked in the ...

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Abstract

The invention discloses an aromatic diamine containing imidazolyl and a preparation method thereof. Tetramines aromatic and aminobenzoic acid are taken as raw materials, and an imidazole ring is formed by reaction between carboxyl and o-amino in a polyphosphoric acid medium, thus preparing 2,2'-bi(4-amino phenyl)-5,5'-bisbenzimidazole, 2,2'-bi(3-amino phenyl)-5,5'-bisbenzimidazole, 2,2'-bi(4-amino phenyl)bisbenzimidazole, 2,2'-bi(3-amino phenyl)bisbenzimidazole, 2,2'-bi(4-amino phenyl)imidazopyridine or 2,2'-bi(3-amino phenyl)imidazopyridine which belong to a novel aromatic diamine containing imidazolyl that is an important monomer raw material for preparing various polyamides and polyimides, so as to enrich the variety of the aromatic diamine containing imidazolyl and polymers, and have broad application prospect in the fields of high-performance fibers, fuel cells and the like.

Description

technical field [0001] The present invention relates to a new type of imidazole group-containing aromatic diamine and its preparation method. Using the prepared substance as a monomer raw material, various high-performance polymers containing imidazole group can be prepared, such as polyamide and polyimide Wait. Background technique [0002] Polybenzimidazole is a class of polybenzimidazoles with excellent thermal stability, high mechanical strength and modulus, excellent chemical stability (especially acid and alkali resistance), good flame retardancy, spinning and film-forming properties High-performance polymer materials have been widely researched and applied in aerospace, military, fire protection, fuel cells and other fields. However, polybenzimidazole is insoluble, infusible, and has poor processability, which limits its industrial application. Although the introduction of groups such as ether bonds or chain hydrocarbons into the polymer structure can improve its pr...

Claims

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Application Information

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IPC IPC(8): C07D235/18C07D487/04C08G69/00C08G73/10
Inventor 房建华郭晓霞徐楠徐宏范晨亮李威
Owner SHANGHAI JIAO TONG UNIV
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