A kind of modified bismaleimide resin and preparation method thereof

A bismaleimide resin, bismaleimide technology, applied in organic chemistry and other directions, can solve the problem that the BEG conversion rate is only 60%, the thermal performance and flexural modulus are reduced, and the crosslinking density of the cured product is reduced, etc. problems, to achieve the effect of easy industrial production, excellent thermal properties and rigidity, and high crosslinking density

Active Publication Date: 2019-04-12
SUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

5,5'-Dieugenol (BEG) is the only raw material of whole biomass-based allylphenyl compounds reported so far for BMI modification (see literature: Mitsuhiro Shibata, Naozumi Tetramoto, Ayumi Imada, Makiyo Neda, Shimon Sugimoto. Reactive & Functional Polymers, 2013, 73, 1086-1095), but the conversion rate of the synthesized BEG is only 60%
This is because BEG is obtained by directly linking two molecules of eugenol, the molecular structure presents a biphenyl structure, and the steric hindrance is large, which makes it more difficult for the Diels-Alder addition reaction between BDM and the double bond of the intermediate to occur, resulting in a cured product Reduced crosslink density, which reduces thermal properties and flexural modulus

Method used

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  • A kind of modified bismaleimide resin and preparation method thereof
  • A kind of modified bismaleimide resin and preparation method thereof
  • A kind of modified bismaleimide resin and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] 1) Preparation of 2,5 furandicarboxylic acid chloride

[0032] See attached figure 1 , Which is the synthesis reaction formula for preparing 2,5 furandicarboxylic acid chloride in this example; the specific reaction conditions are as follows:

[0033] Mix 31.20g of 2,5 furandicarboxylic acid, 35.69g of thionyl chloride and N,N-dimethylformamide (DMF, catalyst, 0.05mL), stir and react at 80℃ for 3h, and cool naturally. At room temperature, the thionyl chloride was evaporated in a vacuum, and after drying, 2,5 furandicarboxylic acid chloride was obtained with a yield of 99.5%.

[0034] 2) Preparation of bis(4-allyl-2-methoxyphenyl)furan-2,5-dicarboxylate based on whole biomass

[0035] See attached figure 2 , It is the synthesis reaction formula for preparing all biomass-based bis(4-allyl-2-methoxyphenyl)furan-2,5-dicarboxylate in this embodiment; the specific reaction conditions are as follows:

[0036] Dissolve 31.20g of eugenol and 24.29g of triethylamine as bases in 200mL of...

Embodiment 2

[0046] 1) Preparation of 2,5 furandicarboxylic acid chloride

[0047] Mix 31.20g of 2,5 furandicarboxylic acid, 35.69g of thionyl chloride and N,N-dimethylformamide (DMF, catalyst, 0.05mL), stir and react at 80℃ for 3h, and cool naturally. At room temperature, the thionyl chloride was evaporated in a vacuum, and after drying, 2,5 furandicarboxylic acid chloride was obtained with a yield of 99.5%.

[0048] 2) Preparation of bis(4-allyl-2-methoxyphenyl)furan-2,5-dicarboxylate based on whole biomass

[0049] Dissolve 32.84g of eugenol and 27.33g of triethylamine as bases in 300mL of dichloromethane and stir, add dropwise a solution of 2,5 furandicarboxylic acid chloride (19.30g) in dichloromethane (300mL) at -2.5±1℃ After the addition, the reaction solution was slowly raised to 20°C, and the reaction was continued for 3 hours; after the reaction, the dichloromethane was evaporated in a vacuum, washed with deionized water, and dried to obtain a total biomass-based bis(4-allyl- The yiel...

Embodiment 3

[0053] 1) Preparation of 2,5 furandicarboxylic acid chloride

[0054] 31.20g 2,5 furandicarboxylic acid, 35.69g thionyl chloride and N,N-dimethylformamide (DMF, catalyst, 0.05mL) were mixed, and the temperature was 70 o The reaction was stirred for 3 hours under the condition of C, cooled to room temperature naturally, and the thionyl chloride was evaporated in a vacuum. After drying, 2,5 furandicarboxylic acid chloride was obtained with a yield of 99.6%.

[0055] 2) Preparation of bis(4-allyl-2-methoxyphenyl)furan-2,5-dicarboxylate based on whole biomass

[0056] Dissolve 34.48g eugenol and 30.36g triethylamine as alkali in 500mL dichloromethane and stir, at -1±1 o Add a solution of 2,5 furandicarboxylic acid chloride (19.30g) in dichloromethane (500mL) under C. After the addition is complete, the reaction solution is slowly raised to 20°C, and the reaction is continued for 4 hours; after the reaction is complete, the dichloride is evaporated by vacuum Methane was washed with deioni...

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Abstract

The invention discloses a modified bismaleimide resin and a preparation method thereof. Biomass-based 2,5 furandicarboxylic acid and thionyl chloride were acylated under the condition of N,N-dimethylformamide as a catalyst to obtain 2,5 furandicarboxylic acid chloride, which was combined with biomass-based clove Phenols were dissolved in dichloromethane, respectively, and esterified under the conditions of tertiary amines to obtain bis(4‑allyl‑2‑methoxyphenyl)furan‑2,5‑dicarboxylates based on whole biomass Ester, which is used to prepare modified bismaleimide resin. The modified bismaleimide resin prepared by the present invention has excellent thermal properties and rigidity; the preparation method adopts 2,5 furandicarboxylic acid and eugenol from biomass, and the raw materials are green, environmentally friendly and renewable, and the production process is simple It has broad application prospects in aerospace, electronic information, electrical insulation and other industrial fields.

Description

Technical field [0001] The present invention relates to a modified bismaleimide resin and a preparation method thereof, in particular to a whole biomass-based bis(4-allyl-2-methyl) synthesized by using green renewable biomass resources. Oxyphenyl) furan-2,5-dicarboxylate modified bismaleimide resin belongs to the technical field of chemical industry and polymer materials. Background technique [0002] In the past few decades, petroleum and coal have been important raw materials for the production of fuels, chemicals, and polymer materials. However, the non-renewability of petroleum and coal resources and the urgency of human sustainable development require the development of a new type of renewable material, and biomass materials just meet the urgent needs of mankind. [0003] Biomass has the characteristics of being renewable, widely distributed and huge annual output, but the utilization efficiency of it has been very low so far. How to efficiently convert renewable biomass res...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G73/12C07D307/54
CPCC07D307/54C08G73/12
Inventor 顾嫒娟缪佳涛梁国正袁莉
Owner SUZHOU UNIV
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