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Side imidazolyl-containing benzidine derivatives and preparation method thereof

A technology of base benzidine and side imidazole, which is applied in the field of side imidazole group-containing benzidine derivatives and their preparation, can solve the problems of restricting the development of imidazole group-containing polymer varieties, few types of imidazole group-containing diamines, and the like, and achieves a rich variety. , good hydrolysis stability, the effect of improving performance

Active Publication Date: 2009-12-02
上海东赤电子科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, due to the very few types of imidazole-based diamines, the development of imidazole-based polymers is limited.

Method used

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  • Side imidazolyl-containing benzidine derivatives and preparation method thereof
  • Side imidazolyl-containing benzidine derivatives and preparation method thereof
  • Side imidazolyl-containing benzidine derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] First, under ice bath conditions, 2.42 g (10 mmol) of raw material 2,2'-dicarboxybiphenyl was dissolved in 25 ml of concentrated sulfuric acid with a mass concentration of 98%, and then 1.4 ml (20.4 mmol) was added dropwise to the solution. ) concentrated nitric acid with a mass concentration of 65%. After the dropwise addition, the reaction condition was maintained at 0°C-5°C, and the reaction was stirred for 10 hours. After the reaction, slowly inject the reaction solution into crushed ice to obtain a yellow solid, which is repeatedly filtered and washed with water to weak acidity, and the solid is collected. The initial product is mixed with ethanol and water (the volume ratio of ethanol / water is 3 / 7-4 / 6) 90 milliliters of mixed solvents were recrystallized to obtain pure 2,2'-dicarboxy 4,4'-dinitrobiphenyl, which was collected by filtration and vacuum-dried for 6 hours at 50°C. The product quality was 2.2 grams, and the yield was 65 %.

[0024] Secondly, under the...

Embodiment 2

[0030]First, under ice-bath conditions, 2.42 grams (10 mmol) of raw material 2,2'-dicarboxybiphenyl was dissolved in 12 milliliters of concentrated sulfuric acid with a mass concentration of 98%, and then 2.1 milliliters (30.6 mmol) were added dropwise to the solution. ) concentrated nitric acid with a mass concentration of 65%. After the dropwise addition, the reaction condition was maintained at 0°C-5°C, and the reaction was stirred for 10 hours. After the reaction, slowly inject the reaction solution into crushed ice to obtain a yellow solid, which is repeatedly filtered and washed with water to weak acidity, and the solid is collected. The initial product is mixed with ethanol and water (the volume ratio of ethanol / water is 3 / 7-4 / 6) 90 milliliters of mixed solvents were recrystallized to obtain pure 2,2'-dicarboxy 4,4'-dinitrobiphenyl, which was collected by filtration and vacuum-dried for 6 hours at 50°C. The product quality was 2.5 grams, and the yield was 74 %.

[003...

Embodiment 3

[0035] First, under ice bath conditions, 2.42 grams (10 mmol) of raw material 2,2'-dicarboxybiphenyl was dissolved in 8 milliliters of concentrated sulfuric acid with a mass concentration of 98%, and then 1.4 milliliters (20.4 mmol) was added dropwise to the solution. ) concentrated nitric acid with a mass concentration of 65%. After the dropwise addition, the reaction condition was maintained at 0°C-5°C, and the reaction was stirred for 10 hours. After the reaction, slowly inject the reaction solution into crushed ice to obtain a yellow solid, which is repeatedly filtered and washed with water to weak acidity, and the solid is collected. The initial product is mixed with ethanol and water (the volume ratio of ethanol / water is 3 / 7-4 / 6) 90 milliliters of mixed solvents were recrystallized to obtain pure 2,2'-dicarboxy 4,4'-dinitrobiphenyl, which was collected by filtration and vacuum-dried for 6 hours at 50°C. The product quality was 2.3 grams, and the yield was 68 %.

[0036...

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Abstract

The invention discloses side imidazolyl-containing benzidine derivatives and a preparation method thereof. In the method, biphenyl-2,2'-dicarboxylic acid serving as a raw material undergoes a nitratlon reaction, a reduction reaction and a imidazole ring-forming reaction to form a 2,2'-diphenyl benzimidazolyl benzidine or a 2,2'-dinaphthyl benzimidazolyl benzidine which is a novel side imidazolyl-containing aromatic diamine. The novel side imidazolyl-containing aromatic diamine is an important monomer raw material for preparing a plurality of polyamides and polyimide, diversifies imidazolyl-containing diamines and polymers, improves the performance of the polymers and has wide application prospects in fields of high-performance fibers, fuel batteries and the like.

Description

technical field [0001] The invention relates to a class of benzidine derivatives containing pendant imidazole groups and a preparation method thereof. Using such substances as monomer raw materials, various high-performance polymers containing pendant imidazole groups, such as polyamides and polyimides, can be prepared. . Background technique [0002] Publication number is that the Chinese invention patent of CN101200822A has reported that the polyimide fiber containing imidazole group has better mechanical properties and heat resistance than the corresponding polyimide fiber without imidazole group; in addition, document J.Membr. Sci.2009, 326, 708-713 reported that the introduction of imidazole group can also endow polyimide film with better anti-free radical oxidation performance, and imidazole group is a basic group that can interact with acid Therefore, introducing imidazole groups into polymers can make polymers absorb acidic substances and endow polymers with more sp...

Claims

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Application Information

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IPC IPC(8): C07D235/18C07D235/02
Inventor 房建华徐楠徐宏郭晓霞徐宏杰印杰
Owner 上海东赤电子科技有限公司
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