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Trifunctional benzoxazine monomer based on resveratrol and preparation method of trifunctional benzoxazine monomer

A technology of resveratrol and benzoxazine, which is applied in the field of trifunctional benzoxazine monomer and its preparation, can solve the problem of long reaction time of biological benzoxazine, insufficient heat resistance, and insufficient thermal performance and other problems, to achieve the effect of being suitable for large-scale production, low equipment requirements and high yield

Active Publication Date: 2019-04-26
成都科宜高分子科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The benzoxazine prepared by the patent number (CN108250382A) uses bisphenolic acid, a bio-based material, but its heat resistance is not good enough, and the carbon residue rate only reaches 50%.
Patent No. (CN107459512A) The reaction time of synthetic biological benzoxazine is too long, it needs to consume a lot of heat energy, and the thermal performance is not excellent enough

Method used

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  • Trifunctional benzoxazine monomer based on resveratrol and preparation method of trifunctional benzoxazine monomer
  • Trifunctional benzoxazine monomer based on resveratrol and preparation method of trifunctional benzoxazine monomer
  • Trifunctional benzoxazine monomer based on resveratrol and preparation method of trifunctional benzoxazine monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] 2-furylamine was used as the amine source.

[0030] Add 1 g (0.0044 mol) of resveratrol, 1.276 g (0.0132 mol) of 2-furan methylamine, and 0.868 g (0.0289 mol) of paraformaldehyde into the flask, add 50 ml of toluene solution, connect a condenser tube, and stir at 110 ° C And react for 4h. The filtrate after the reaction was rotary evaporated to remove the solvent to obtain 1.8 g of benzoxazine monomer with a yield of 68%. The chemical reaction equation is as follows:

[0031]

[0032] In the present embodiment, the obtained oxazine product structure is:

[0033]

[0034] The proton nuclear magnetic resonance spectrum, Fourier transform infrared transform spectrum, DSC curve and thermogravimetric curve of this product are shown in the appendix figure 1 , attached figure 2 , attached image 3 And attached Figure 4 .

[0035] attached figure 1 Proton NMR spectrum. Chemical shifts around 4.8ppm and 3.9ppm are characteristic peaks of methylene on the oxazine...

Embodiment 2

[0037] The amine source compound 2-furylmethylamine in Example 1 was replaced by aniline. Other steps are the same as those in Example 1.

[0038] Wherein the specific chemical structural formula of aniline is: The amount of reactants was changed to: weigh 1.14g (0.005mol) of resveratrol, 1.40g (0.015mol) of aniline, and 0.99g (0.033mol) of paraformaldehyde, with a yield of 79%.

[0039]

[0040] The curing exothermic peak temperature of the trifunctional benzoxazine monomer obtained in this example is 230°C. After further curing and crosslinking, the temperature of the polybenzoxazine resin is 353°C when the thermal weight loss is 5%, and the inert gas atmosphere is 800°C. , the carbon residue rate is 61%, and the heat release energy of the flame retardant test result is 79Jg -1 K -1 .

Embodiment 3

[0042] The amine source compound 2-furylmethylamine in Example 1 was replaced by 4-chloroaniline. Other steps are the same as those in Example 1.

[0043] Wherein the concrete chemical structural formula of 4-chloroaniline is: The amount of reactants was changed to: weigh 1.14g (0.005mol) of resveratrol, 1.91g (0.015mol) of 4-chloroaniline, and 0.99g (0.033mol) of paraformaldehyde, with a yield of 75%.

[0044]

[0045] The exothermic peak temperature of the benzoxazine obtained in this example is 233°C. After further curing and crosslinking, the temperature of the polybenzoxazine resin is 357°C when the thermal weight loss is 5%, and the carbon residue is 800°C in an inert gas atmosphere The rate is 62%, and the heat release energy of the flame retardant test result is 73Jg -1 K -1 .

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Abstract

The invention belongs to the technical field of thermosetting resin, and provides a trifunctional benzoxazine monomer based on resveratrol and a preparation method of the trifunctional benzoxazine monomer. The method comprises the following steps: mixing resveratrol, an amine compound and paraformaldehyde, adding a low-polarity solvent as a reaction solvent, reacting for 2 to 6 hours at 80 to 130DEG C, filtering after reaction, washing filter liquor with water, and performing rotary evaporation and drying to obtain a product. The method has the advantages that bio-based phenol is utilized, asynthesized target product is the trifunctional benzoxazine monomer, the synthesis steps are simple, the yield is relatively high, cured benzoxazine resin has very excellent thermal property and mechanical property, the flame resistance is excellent, the synthesis technology is simple, the requirements on equipment are low, and the method is suitable for scale production.

Description

technical field [0001] The invention belongs to the technical field of thermosetting resins, in particular to a bio-based resveratrol-based trifunctional benzoxazine monomer and a preparation method thereof. Background technique [0002] Benzoxazine polymers are a class of thermosetting polymers developed in recent years, and they have attracted people's attention due to their obvious advantages over traditional thermosetting resins. Benzoxazine resin has excellent properties such as excellent heat resistance, good mechanical properties, close to zero polymerization shrinkage, very flexible molecular design, high coke yield, and low surface energy. After complete curing, the glass transition temperature is high and has good heat resistance; after the ring-opening polymerization of benzoxazine, it has a structure similar to that of phenolic resin, which makes its electrical insulation performance good; When the oxazine resin is at a certain temperature, it can be cured witho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/04
CPCC07D498/04
Inventor 张侃韩梦超刘宇奇
Owner 成都科宜高分子科技有限公司
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