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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: 2017-05-24
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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  • Modified bismaleimide resin and preparation method thereof
  • Modified bismaleimide resin and preparation method thereof
  • 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 , it is the synthetic reaction formula of preparing 2,5 furandicarboxylic acid chloride in the present embodiment; Concrete reaction condition is 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°C for 3h, and cool naturally After reaching room temperature, thionyl chloride was evaporated in vacuo, 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 , which is the synthesis reaction formula for preparing bis(4-allyl-2-methoxyphenyl)furan-2,5-dicarboxylate based on whole biomass in this example; the specific reaction conditions are as follows:

[0036] Dissolve 31.20g of eugenol and 24.29g of triethylami...

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°C for 3h, and cool naturally After reaching room temperature, thionyl chloride was evaporated in vacuo, 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 a base in 300mL of dichloromethane and stir, and drop into a solution of 2,5 furandicarboxylic acid chloride (19.30g) in dichloromethane (300mL) at -2.5±1°C After the dropwise 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 vacuo, washed with deionized water, and dried to obtain bis(4-allyl- 2-methoxy...

Embodiment 3

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

[0054] Mix 31.20 g of 2,5 furandicarboxylic acid, 35.69 g of thionyl chloride and N,N-dimethylformamide (DMF, catalyst, 0.05 mL) at 70 o The reaction was stirred under the condition of C for 3 h, cooled naturally to room temperature, thionyl chloride was evaporated in vacuum, and 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 base in 500mL dichloromethane and stir at -1±1 o Add a solution of 2,5-furandicarboxylic acid chloride (19.30g) in dichloromethane (500mL) dropwise at C, and after the dropwise addition, the reaction solution slowly rises to 20°C, and the reaction is continued for 4 hours; methane, washed with deionized water, and dried to obtain bis(4-allyl-2-methoxyphenyl)furan-2,5-dicarboxylate in a yield o...

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Abstract

The invention discloses a modified bismaleimide resin and a preparation method thereof. The method comprises the following steps: acidating biomass-based 2, 5-furandicarboxylic acid and thionyl chloride under the condition of using N,N-dimethyl formamide as the catalyst to obtain 2,5-furandicarbonyl dichloride, respectively dissolving the 2,5-furandicarbonyl dichloride and biomass-based eugenol in dichloromethane, and carrying out an esterification reaction under the condition of tertiary amine to obtain bis(4-allyl-2-methoxyphenyl)furan-2,5-dicarboxylic ester based on total biomass, and using the bis(4-allyl-2-methoxyphenyl)furan-2,5-dicarboxylic ester to prepare the modified bismaleimide resin. The modified bismaleimide resin prepared by the invention has excellent thermal performance and rigidity; and the preparation method adopts the biomass-based 2,5-furandicarboxylic acid and the biomass-based eugenol, the raw materials are green, environment-friendly and renewable, and the production process is simple, and the resin has a wide application prospect in the fields of aerospace, electronic information, electrical insulation and the like.

Description

technical field [0001] The invention relates to a modified bismaleimide resin and a preparation method thereof, in particular to a kind of bis(4-allyl-2-formaldehyde) based on whole biomass synthesized by using green renewable biomass resources The invention relates to a bismaleimide resin modified by oxyphenyl)furan-2,5-dicarboxylate, which belongs to the technical field of chemical industry and polymer materials. Background technique [0002] Over 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 human beings. [0003] Biomass has the characteristics of renewable, wide distribution and huge annual output, but its utilization efficiency is very low so far. How to ef...

Claims

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Application Information

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Patent Type & Authority Applications(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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