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Sulfonyl-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 single polyimide functional group type, polyimide film is easy to break, polyimide development restrictions, etc., to achieve good solubility The effect of safety, cost saving and simple operation

Pending Publication Date: 2022-05-27
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the polyimide prepared by it is relatively single due to the type of functional groups on it, which leads to the easy fracture of the prepared polyimide film during use; meanwhile, although polyimide has great excellent performance, However, compared with other polymers, the cost is too high, which leads to great limitations in the development of polyimides.

Method used

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

Examples

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Effect test

Embodiment 1

[0076] (1) under the protection of nitrogen, into the three-necked flask equipped with mechanical stirring, add the molar ratio of 2.0:1.0 with substituent R 1 The obtained p-aminophenol A and m-dihalobenzenesulfonyl compound B were further added with an appropriate amount of organic solvent and basic catalyst, stirred at room temperature for half an hour, and then heated to 70 °C for 7 hours to complete the reaction.

[0077] (2) A white aromatic diamine monomer can be obtained after precipitation, filtration, drying and recrystallization.

[0078] The specific results are Figure 1-2 shown.

[0079] Wherein, 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 the amount thereof is the same as that of the p-amino group. The mass ratio of the amount and the amount of the phenol and the m-dihalobenzenesulfonyl compound is 3.0: 1.0; the basic catalyst is selected as potassium hydroxide, and the mass ...

Embodiment 2-9

[0085] The specific embodiment is the same as Example 1, the difference is that the reaction temperature, reaction time and the molar ratio of the raw materials will be somewhat different. The specific setting parameters and the purity of the target product are shown in Table 1.

Embodiment 10

[0087] (1) Under the protection of ammonia gas, in a three-necked flask equipped with mechanical stirring, add a molar ratio of 3.0:1.0 with substituent R 1 The p-aminophenol A and the m-dihalobenzenesulfonyl compound B were further added with an ionic liquid catalyst, stirred at room temperature for half an hour, heated to 80 °C and reacted for 10 hours, and the reaction was terminated.

[0088] (2) The product obtained by the reaction is centrifuged, and the solid obtained by centrifugation is washed, dried and recrystallized to obtain a white aromatic diamine monomer.

[0089] Wherein, the rotating speed of centrifugation is 5000rpm, the time of centrifugation is 30min, and the selected ionic catalyst is ionic catalyst 1, and the structural formula of described ionic catalyst 1 is The mass ratio of its consumption to the consumption of the p-aminophenol and the m-dihalobenzenesulfonyl compound is 3.0:1.0; the alcohol used during recrystallization is methanol; Ar 1 Select ...

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Abstract

The invention provides a sulfonyl-containing polysubstituted aromatic diamine monomer and a preparation method thereof, the structural formula of the sulfonyl-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 a sulfuryl structure, and can further improve the potential application values of dissolving 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 preparation of diamine monomers, in particular to a sulfone group-containing polysubstituted aromatic diamine monomer and a preparation method thereof. Background technique [0002] Polyimide is an organic polymer material, its high temperature resistance is above 400 ℃, the long-term use temperature range is between 200-300 ℃, and it has high insulation performance, and because polyimide has such good performance, its It has become a special engineering material widely used in aviation, aerospace, microelectronics, nano, liquid crystal, separation membrane and laser. [0003] The polyimide prepared by the prior art is mainly by introducing hexafluoroisopropyl into the molecular chain of the polymer. Due to the large free volume of hexafluoroisopropyl, the intermolecular force of the polymer can be reduced. , while also increasing the solubility of the polymer. [0004] However, the polyimide prepared by it has a...

Claims

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Application Information

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IPC IPC(8): C07D239/80C07D401/14C07D413/14C07D417/14C08G73/10C08J5/18C08L79/08
CPCC07D417/14C07D413/14C07D401/14C07D239/80C08G73/1007C08G73/1085C08J5/18C08J2379/08Y02P20/54
Inventor 谢劲吴晓鹏朱成建
Owner NANJING UNIV
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