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Bio-based dibenzoxazine monomer and preparation method thereof

A benzoxazine and bio-based technology, applied in the field of thermosetting resin and its preparation, can solve the problems of limited application prospects, poor mechanical properties and thermal stability, etc., and achieve simple synthesis process, low equipment requirements, and excellent heat resistance and the effect of flame retardancy

Active Publication Date: 2020-05-05
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because traditional bio-based materials do not contain benzene ring structure, their mechanical properties and thermal stability are poor, and their application prospects are limited.

Method used

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  • Bio-based dibenzoxazine monomer and preparation method thereof
  • Bio-based dibenzoxazine monomer and preparation method thereof
  • Bio-based dibenzoxazine monomer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] (1) 4.966g (0.04mol) of guaiacol, 1.922g (0.02mol) of furfural, and a 20% sodium hydroxide solution (wherein the quality of sodium hydroxide is 0.496g) in the flask are added into the flask, React at 60°C for 8 hours, then raise the temperature to 120°C and continue to react for 12 hours. After the reaction, it was washed with alkali and purified by acidification to obtain 4.89 g of intermediate bio-based bisphenol with a yield of 75%. The chemical reaction equation is as follows:

[0034]

[0035] (2) Add 1.63g (0.005mol) of bio-based bisphenol obtained in step (1), 0.97g (0.01mol) of 2-furylmethylamine, 0.868g (0.0289mol) of paraformaldehyde into the flask, and add 50ml of toluene solution , Connected to a condenser, stirred and reacted at 110°C for 4h. The filtrate after the reaction was rotary evaporated to remove the solvent to obtain 2.27 g of benzoxazine monomer with a yield of 80%. The chemical reaction equation is as follows:

[0036]

[0037] In the ...

Embodiment 2

[0041] The reactant 2-furan methylamine of step (2) in embodiment 1 is replaced with 3-methylaniline, and the amount of reactant is changed accordingly, and other operating steps are with the steps in embodiment 1.

[0042] In the second step reaction, the amount of the reactant was changed to: 1.63g (0.005mol) of bio-based bisphenol obtained from the previous step reaction, 1.07g (0.01mol) of 3-methylaniline and 0.868 (0.0289mol) of paraformaldehyde ) to react, finally obtain product 2.29g, yield 78%.

[0043] Wherein the specific chemical structure of the benzoxazine monomer obtained is:

[0044]

[0045] The exothermic peak temperature of the curing benzoxazine obtained in this example is 251°C. After further curing and cross-linking, the temperature of the polybenzoxazine resin is 366°C when the thermal weight loss is 10%. When the inert gas atmosphere is 800°C, the carbon residue The rate is 61%, and the heat release energy of the flame retardant test result is 89Jg ...

Embodiment 3

[0047] The reactant 2-furyl methylamine in the second step in the embodiment 1 is replaced with 3-fluoroaniline, and the amount of the reactant is changed accordingly, and other operation steps are with the steps in the embodiment 1.

[0048]In the second step reaction, the amount of the reactant was changed to: 1.63g (0.005mol) of bio-based bisphenol obtained from the previous step reaction, 1.11g (0.01mol) of 3-methylaniline and 0.868 (0.0289mol) of paraformaldehyde ) to react to obtain product 2.15g, yield 72%.

[0049] Wherein the specific chemical structure of the benzoxazine monomer obtained is:

[0050]

[0051] The exothermic peak temperature of the curing benzoxazine obtained in this example is 258°C. After further curing and crosslinking, the temperature of the polybenzoxazine resin is 371°C when the thermal weight loss is 10%. When the inert gas atmosphere is 800°C, the carbon residue The rate is 63%, and the heat release energy of the flame retardant test resul...

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Abstract

The invention belongs to the technical field of thermosetting resin and discloses a bio-based dibenzoxazine monomer and a preparation method thereof. The preparation method comprises the following steps: using bio-based guaiacol and furfural as raw materials to prepare a diphenol compound, then mixing the bio-based diphenol compound, an amine compound and paraformaldehyde and then adding into a low-polarity solvent, reacting for 4-14 hours at the temperature of 90-120 DEG C, purifying substances in a reaction liquid after the reaction is stopped, and vacuum-drying to obtain the bio-based dibenzoxazine monomer. The preparation method has the advantages that the bis-benzoxazine monomer is synthesized by using the bio-based raw materials, the synthesis steps are simple, the yield is relatively high, and the cured benzoxazine resin has very excellent thermal and mechanical properties and excellent flame retardance; the synthesis process is simple, has low requirements on equipment, and issuitable for large-scale production.

Description

technical field [0001] The invention belongs to the technical field of thermosetting resin and its preparation, in particular to a method for preparing a bio-based bisbenzoxazine monomer. Background technique [0002] Benzoxazines are a class of thermosetting resins that have developed rapidly in recent years. Compared with traditional resins such as phenolic resin and epoxy resin, benzoxazine has good thermal stability, excellent flame retardancy, high mechanical strength and stable insulation. In addition, during the polymerization process, benzoxazine avoids the disadvantages of the volume shrinkage of the material caused by the formation of small molecules in the process of polycondensation and curing of traditional phenolic resins and the formation of microporous structures in the material. rate is zero. It can take advantage of its excellent molecular design flexibility to prepare the desired benzoxazine resin with specific functions by changing the functional groups...

Claims

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Application Information

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IPC IPC(8): C07D413/14C08G14/073C08K5/357
CPCC07D413/14C08G14/06C08K5/357
Inventor 张侃杨蕊韩梦超郝柏然
Owner JIANGSU UNIV
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