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Amide-containing polysubstituted aromatic diamine monomer and preparation method thereof

An aromatic diamine and multi-substitution technology, which is applied in the field of diamine monomer preparation, can solve the problems of inorganic alkali mechanical equipment corrosion, release huge heat, environmental pollution, etc., and achieve the effects of good solubility, low energy consumption and simple operation.

Pending Publication Date: 2022-05-20
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, in the process of synthesizing diamine monomers of existing polyimides, the addition of a large amount of inorganic bases will cause corrosion of mechanical equipment, and a huge amount of heat will be released during the reaction process, which is difficult to control and has certain dangers. , but also cause environmental pollution

Method used

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  • Amide-containing polysubstituted aromatic diamine monomer and preparation method thereof
  • Amide-containing polysubstituted aromatic diamine monomer and preparation method thereof
  • Amide-containing polysubstituted aromatic diamine monomer and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0075] (1) Under the protection of nitrogen, add the substituent R with a molar ratio of 3.0:1.0 into a three-necked flask equipped with mechanical stirring. 1 The p-aminophenol A and m-dihalobenzamide compound B were further added with an appropriate amount of organic solvent and basic catalyst, stirred at room temperature for half an hour, then heated to 100°C for 10 hours, and then the reaction was terminated.

[0076] (2) White aromatic diamine monomer can be obtained after precipitation, filtration, drying and recrystallization.

[0077] Among them, the organic solvent selected in this embodiment is a mixture of 1,4-dioxane and N,N-dimethylformamide in a mass ratio of 4:6, and its dosage is the same as that of the para-amino The mass ratio of the amount of phenol and the m-dihalobenzamide compound is 3.0:1.0; the basic catalyst is potassium carbonate, and the mass ratio of its amount to the amount of p-aminophenol is 2.0:1.0; The alcohol that adopts during recrystallizat...

Embodiment 2-9

[0081] The specific implementation method is consistent with Example 1, except that the reaction temperature, reaction time and molar ratio of raw materials will be somewhat different. The specific setting parameters and the purity of the target product are shown in Table 1.

Embodiment 10

[0083] (1) Under the protection of ammonia gas, in a three-necked flask equipped with mechanical stirring, add a molar ratio of 2.0:1.0 with substituent R 1 The p-aminophenol A and m-dihalobenzamide compound B were further added with ionic liquid catalysts respectively, stirred at room temperature for half an hour, then heated to 60°C for 7 hours, and then the reaction was terminated.

[0084] (2) The product obtained by the reaction is centrifuged, and the solid obtained by the centrifugation is washed, dried and recrystallized to obtain a white aromatic diamine monomer.

[0085] Wherein, the rotating speed of centrifugal is 5000rpm, and the time of centrifugal is 30min, and the ion catalyst selected is ion catalyst 1, and the structural formula of described ion catalyst 1 is The mass ratio of its amount to the amount of the p-aminophenol and the m-dihalobenzamide compound is 2.0:1.0; the alcohol used for recrystallization is methanol; Ar1 Choose as: Ar 2 choose as The ...

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Abstract

The invention provides an amide-containing polysubstituted aromatic diamine monomer and a preparation method thereof, the structural formula of the amide-containing polysubstituted aromatic diamine monomer is shown in the specification, R1 and R2 are one of-H,-CF3,-OCH3 or alkyl, R3 is one of aryl or alkyl, and Ar1 and Ar2 are aromatic rings or aromatic heterocyclic rings. The invention provides two preparation methods, one is a base catalysis synthesis method, and the other is an ionic liquid catalysis method. The diamine monomer can be applied to the preparation of a high-performance polyimide film material containing an amide structure, and can further improve the potential application values of dissolution film-forming property, optical transparency, tensile strength property, dielectric loss property and the like of the prepared polyimide film material.

Description

technical field [0001] The invention relates to the field of diamine monomer preparation, in particular to an amide-containing multi-substituted aromatic diamine monomer and a preparation method thereof. Background technique [0002] Polyimide film is made by casting polyamic acid solution, stretching, and imidizing at high temperature. The film is yellow and transparent, and has outstanding high temperature resistance, radiation resistance, and Chemical corrosion and electrical insulation properties, especially suitable for flexible printed circuit board substrates and electrical insulation materials for various high temperature resistant motors. [0003] Thermal recovery polyimide has excellent thermal stability, chemical corrosion resistance and mechanical properties, high tensile strength, and a wide range of applications. It can be used from minus one hundred degrees to two or three hundred degrees. , At the same time, the chemical properties of polyimide are stable, a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C07C215/76C07C235/64C07D213/81C07D239/52C07D239/80C07D307/66C07D403/14C07D405/14C07D409/14C07D413/14C07D417/14C08G73/10
CPCC07D213/81C07D413/14C07D417/14C07D401/14C07C235/64C07D239/52C07D403/14C07D239/80C07D405/14C07D409/14C07D307/66C07C215/76C08G73/1085C08G73/1046Y02P20/54
Inventor 谢劲夏嗣禹朱成建
Owner NANJING UNIV
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