Aminopyrene type benzoxazine compound and preparation method thereof

A technology for benzoxazine and compounds, which is applied in the field of benzoxazine compounds containing pyrene substituents and its preparation, can solve problems affecting the full play of properties, carbon nanotube structure damage, poor compatibility, etc., and achieve a wide range of Application prospects, the effect of good interface compatibility

Active Publication Date: 2014-12-24
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, clay, carbon nanotubes, polyhedral silsesquioxane (POSS) and other modified benzoxazine resins are mostly used to improve the performance of benzoxazine resins, but the improvement is not large, such as strong acid modified carbon nano The structure of carbon nanotubes will be damaged to a certain extent, which will affect the full play of its properties, and there is still a problem of poor compatibility between carbon nanotubes and benzoxazine resins.

Method used

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  • Aminopyrene type benzoxazine compound and preparation method thereof
  • Aminopyrene type benzoxazine compound and preparation method thereof
  • Aminopyrene type benzoxazine compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Adopt solution method to prepare 3,4-dihydro-3-pyrenyl-1,3-benzoxazine, i.e. pyreneamine-phenol type benzoxazine, its structural formula is as follows:

[0057]

[0058] Add pyreneamine (2.17g, 10.0mmol) and phenol (0.94g, 10.0mmol) into a three-necked flask at room temperature, stir to dissolve in about 100ml of toluene. Add paraformaldehyde (0.6g, 20.0mmol) into the three-necked flask in batches, continue to stir to make the mixture uniform, and then gradually raise the temperature to 95°C for reflux. The reaction stopped after 3 hours, and was left to cool to obtain a reddish-brown solution. After washing with 1mol / L NaOH and deionized water, toluene was removed by rotary evaporation, and then vacuum-dried for 24 hours, the obtained reddish-brown crystal product was pyreneamine-phenol-type benzoxazine with a yield of 75.8%.

Embodiment 2

[0060] Prepare 2,2-bis(3,4-dihydro-3-pyrenyl-1,3-benzoxazine) propane by solution method, i.e. pyreneamine-bisphenol A type benzoxazine, its simplified structure as follows:

[0061]

[0062]Add pyreneamine (4.34g, 20.0mmol) and bisphenol A (2.28g, 10.0mmol) into a three-necked flask at room temperature, stir to dissolve in about 96ml of toluene. Add paraformaldehyde (1.2g, 40.0mmol) into the three-necked flask in batches, continue stirring to make the mixture uniform, and then gradually raise the temperature to 95°C for reflux. The reaction stopped after 3 hours, and was left to cool to obtain a reddish-brown solution. After washing with 1mol / L NaOH and deionized water, the toluene was removed by rotary evaporation, and then vacuum-dried for 24 hours. The obtained reddish-brown crystal product was pyrenamine-bisphenol A benzoxazine with a yield of 75.5%.

Embodiment 3

[0063] Embodiment 3 adopts solution method to prepare i.e. pyreneamine-p-cresol type benzoxazine, and its structural formula is as follows:

[0064]

[0065] Add pyreneamine (2.17g, 10.0mmol) and p-cresol (1.08g, 10.0mmol) into a three-necked flask at room temperature, and stir to dissolve in 100ml of toluene. Add paraformaldehyde (0.6g, 20.0mmol) into the three-necked flask in batches, continue to stir to make the mixture uniform, and then gradually raise the temperature to 95°C for reflux. The reaction stopped after 3 hours, and was left to cool to obtain a reddish-brown solution. After washing with 1mol / L NaOH and deionized water, the toluene was removed by rotary evaporation, and then vacuum-dried for 24 hours to obtain a reddish-brown crystal product which was pyreneamine-p-cresol benzoxazine with a yield of 65.5%.

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Abstract

The invention discloses an aminopyrene type benzoxazine compound and a preparation method thereof. The preparation method comprises the following steps: evenly mixing a phenolic hydroxyl-containing phenol compound, aminopyrene and an aldehyde compound through a solvent, then heating to 60-120DEG C for refluxing, reacting for 2-6 hours, and heating, and dehydrating and cyclizing a reaction mixture to obtain the aminopyrene type benzoxazine compound, wherein the mole ratio of the phenol group to amine group to aldehyde group is 1:1:(2-4). The aminopyrene type benzoxazine compound prepared by adopting the preparation method and a carbon material (such as carbon nanotubes and graphene) have excellent phi-phi interaction, and the aminopyrene type benzoxazine compound has excellent interfacial compatibility together with the carbon material.

Description

technical field [0001] The invention relates to the field of benzoxazine resins, in particular to benzoxazine compounds containing pyrene substituents and a preparation method thereof. Background technique [0002] Benzoxazines are intermediates of a class of six-membered heterocyclic compounds composed of nitrogen and oxygen atoms synthesized from phenolic compounds, aldehydes and primary amine compounds. Cyclopolymerization produces nitrogen-containing networks similar to phenolic resins, called benzoxazine resins. In addition to the excellent properties of traditional phenolic resins such as heat resistance, flame retardancy, excellent dielectric properties, chemical properties, low water absorption, and low cost, benzoxazine resin does not emit small molecules during the curing process, and the finished product Zero shrinkage or slight expansion, the polymer has special advantages such as low thermal expansion coefficient, good high temperature resistance and mechanical...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/16C07D413/14C08K5/357C08K5/41C08L79/04
CPCC07D265/16C07D413/14
Inventor 徐日炜
Owner BEIJING UNIV OF CHEM TECH
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