Asymmetric aromatic diamine containing 1,3,4-oxadiazole structure and preparation method thereof

An aromatic diamine, asymmetric technology, applied in the field of chemical intermediate synthesis, can solve the problems of high rigidity, poor polymer toughness and solubility, and achieve the effect of good heat resistance and excellent performance

Inactive Publication Date: 2013-04-03
SHENYANG AEROSPACE UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The present invention mainly solves the problem that most of the existing diamines used for synthesizing bismaleimide are symmetrical in structure and high in rigidity, resulting in poor toughness and solubility of polymers

Method used

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  • Asymmetric aromatic diamine containing 1,3,4-oxadiazole structure and preparation method thereof
  • Asymmetric aromatic diamine containing 1,3,4-oxadiazole structure and preparation method thereof
  • Asymmetric aromatic diamine containing 1,3,4-oxadiazole structure and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0033] (A) Add 0.1mol of p-chloronitrobenzene, 0.12mol of anhydrous potassium carbonate, 0.11mol of p-cresol, and 60ml of N,N-dimethylformamide into the reaction kettle, and react 12 at 120°C hour; filtered while hot, cooled the filtrate, added cold water, precipitated, filtered, washed the filter cake three times with distilled water, filtered, and dried in vacuum to obtain light yellow 4-methyl-4'-nitrodiphenyl ether, the yield was 96.3 %, the purity determined by HPLC is 99.6%, and the melting point is 67°C. FT-IR (KBr, cm -1 ): 2946, 2920 (-CH 3 ), 1509, 1343 (-NO 2 ), 1248, 1111 (Ar-O).

[0034] (B) Add 0.1mol of 4-methyl-4'-nitrodiphenyl ether, 0.5mol of sodium hydroxide, 50ml of water, and 100ml of pyridine into the reaction kettle, stir to dissolve, and then add 0.5mol of potassium permanganate Add to the reaction kettle in batches, react at 90°C for 10 hours, cool, filter, acidify the filtrate with acid, a white solid precipitates, filter and dry to obtain 4-p-nit...

Embodiment 2

[0041] (A) Add 0.1mol of p-chloronitrobenzene, 0.12mol of anhydrous potassium carbonate, 0.11mol of m-cresol, and 50ml of N,N-dimethylformamide into the reaction kettle, and react 10 at 125°C hour; filtered while hot, cooled the filtrate, added cold water, precipitated, filtered, washed the filter cake three times with distilled water, filtered, and vacuum-dried to obtain light yellow 3-methyl-4'-nitrodiphenyl ether, yield 97.1 %, the purity determined by HPLC is 99.3%, and the melting point is 62°C. FT-IR (KBr, cm -1 ): 2923, 2951 (-CH 3 ), 1501, 1345 (-NO 2 ), 1250, 1108 (Ar-O).

[0042] (B) Add 0.05mol of 4-methyl-3'-nitrodiphenyl ether, 0.3mol of sodium hydroxide, 30ml of water, and 70ml of pyridine into the reaction kettle, stir to dissolve, and then add 0.3mol of potassium permanganate Add to the reactor in batches, react at 95°C for 9 hours, cool, filter, acidify the filtrate with acid, a white solid precipitates, filter and dry to obtain 3-p-nitrophenoxybenzoic aci...

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Abstract

The invention discloses an asymmetric aromatic diamine containing a 1,3,4-oxadiazole structure and a preparation method thereof, and mainly aims at solving the problems that most of the existing diamines for synthesizing bismaleimide are in a symmetric structure and have high rigidity and consequently the toughness and solubility of the polymer are low. The diamine has a structural formula shown in the specification, wherein the substituent group Ar in the diamine structure is shown in the specification. The preparation method comprises the following steps of: obtaining an N,N'-dihydrazide compound through four steps of main reactions; dehydrating under the effect of a dehydrating agent to obtain an asymmetric aromatic dinitro-compound containing the 1,3,4-oxadiazole structure; and reducing the asymmetric aromatic dinitro-compound containing the 1,3,4-oxadiazole structure to obtain a novel asymmetric aromatic diamine monomer containing the 1,3,4-oxadiazole structure. According to the invention, by introducing an oxadiazole heterocyclic ring and an ether bond, the resin synthesized by taking the asymmetric aromatic diamine containing the 1,3,4-oxadiazole structure as an intermediate has good heat resistance and certain flexibility; and the diamine can be used for synthesizing bismaleimide with excellent performance.

Description

technical field [0001] The invention belongs to the technical field of chemical intermediate synthesis, and in particular relates to a class of asymmetric aromatic diamines containing 1,3,4-oxadiazole structure and a preparation method thereof. Background technique [0002] Aromatic diamines are important intermediates in organic synthesis, and the synthesis and research of new diamines have also attracted widespread attention. Diamine compounds can be used to synthesize new polyimides, polyamides, etc., and can also be used as curing agents for epoxy resins. 1,3,4-Oxadiazole and its derivatives have biological activity and are widely used in medicine, agriculture and other fields. Many literatures have reported the synthesis and performance research of bismaleimides containing 1,3,4-oxadiazole structure, but most of them have symmetrical structures and high rigidity, resulting in poor toughness and solubility of polymers. Designing and synthesizing aromatic diamines with ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D271/107
Inventor 陈平夏连连熊需海卢放于祺
Owner SHENYANG AEROSPACE UNIVERSITY
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