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Bismaleimide containing fluorenyl group and aryl ether bond structure and preparation method thereof

A technology of bismaleimide and bismaleimide acid is applied in the field of bismaleimide and its preparation, and can solve the problems of high melting temperature of bismaleimide, difficulty in melting processing, and the like, Achieving the effect of lowering melting point, broadening the melt processing window, and increasing solubility

Active Publication Date: 2015-10-28
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Document 1 (Journal of Applied Polymer Science, 2008, 107) reported three chain-extended fluorenyl bismaleimide monomers containing imide bonds, whose solubility has been significantly improved and can be dissolved in chloroform , dichloromethane, tetrahydrofuran, N,N-dimethylformamide and other solvents, but the melting temperature of bismaleimide with this structure is still high, and the melting peak is a broad peak, which is between 240-300 ° C The melting point and solidification temperature are relatively close, so that melting and solidification occur together, and the heat release of solidification is concentrated, making melting processing difficult
However, bismaleimides containing both high heat-resistant oxidative fluorene rings and rotatable aryl ether linkages and their preparation methods have not yet been published in patents or literature reports.

Method used

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  • Bismaleimide containing fluorenyl group and aryl ether bond structure and preparation method thereof
  • Bismaleimide containing fluorenyl group and aryl ether bond structure and preparation method thereof
  • Bismaleimide containing fluorenyl group and aryl ether bond structure and preparation method thereof

Examples

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Embodiment 1

[0028] Example 1: 9,9-bis[4-(4-maleimidophenoxy)phenyl]fluorene

[0029] (1) Dissolve maleic anhydride (0.21mol) in 20ml of acetone and stir to dissolve. Dissolve aromatic diamine I (0.1mol) containing fluorenyl group and aryl ether bond structure in 80ml of acetone, slowly drop into the acetone solution of maleic anhydride, and react at room temperature for 8 hours. After the reaction, the resulting yellow solid was filtered, and the filter cake was vacuum-dried to obtain bismaleimide acid II containing a fluorenyl group and an aryl ether bond structure, with a yield of 92.7% and a purity of 99.5% as determined by HPLC. FT-IR (KBr, cm -1 ): 3288, 1543 (-NH), 1712 (-C=O).

[0030] (2) Suspend bismaleimide acid II (0.1mol) generated in the previous step in 200ml of acetone, add 0.15g of sodium acetate, heat to 50°C, add dropwise 18ml of triethylamine and 40ml of acetic anhydride, and wait for the reaction After the solution became homogeneous, it was reacted at constant temp...

Embodiment 2

[0032] Example 2: 9,9-bis[4-(4-maleimidophenoxy)-3-methylphenyl]fluorene

[0033] (1) Dissolve maleic anhydride (0.21mol) in 20ml of acetone and stir to dissolve. Dissolve aromatic diamine I' (0.1mol) containing methylfluorene and aryl ether bond structure in 80ml of acetone, slowly add it dropwise into the acetone solution of maleic anhydride, and react at room temperature for 8 hours. After the reaction, the resulting yellow solid was filtered, and the filter cake was vacuum-dried to obtain bismaleimide acid II' containing methylfluorene and aryl ether bond structure, with a yield of 91.2% and a purity of 99.5% as determined by HPLC. FT-IR (KBr, cm -1 ): 3282, 1550 (-NH), 2958, 2916 (-CH 3 ), 1707 (-C=O).

[0034] (2) Suspend the bismaleimide acid II' (0.1mol) generated in the previous step in 200ml of acetone, add 0.15g of sodium acetate, heat to 50°C, add dropwise 18ml of triethylamine and 40ml of acetic anhydride, and wait After the reaction liquid became homogeneous,...

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Abstract

The present invention provides a kind of bismaleimide containing fluorenyl group and aryl ether bond structure and its preparation method. The bismaleimide containing fluorenyl group and aryl ether bond structure has the following structural formula: the substituent R1 in the formula , R2 are each independently selected from a hydrogen atom, a halogen atom, a nitro group, a C1-C20 aliphatic alkyl group or a derivative thereof, or a C6-C12 aromatic hydrocarbon alkyl group or a derivative thereof.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, and in particular relates to a bismaleimide containing a fluorenyl group and an aryl ether bond structure and a preparation method thereof. Background technique [0002] Bismaleimide is an important thermosetting resin with good high temperature resistance, radiation resistance, heat and humidity resistance, chemical corrosion resistance, high strength, high modulus and high temperature resistance and other excellent properties. However, bismaleimide is insoluble in common solvents, its high melting point and brittleness after curing limit its application. There are many ways to improve the toughness of bismaleimide resin, and designing and synthesizing a new type of bismaleimide with flexible chain and aromatic ring structure in the main chain is one of the effective methods to improve its performance. [0003] Because polymers containing fluorenyl structures have high glass transitio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/452
Inventor 张丽影陈平赵小菁夏连连熊需海范圣第
Owner DALIAN UNIV OF TECH