Synthesis and application of epoxy resin based on catechuic acid

A technology of catechin epoxy resin and epoxy resin, applied in the direction of organic chemistry, etc., can solve many problems such as use

Pending Publication Date: 2020-04-21
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Although epoxy resin has a wide range of uses, there are still many problems in its use

Method used

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  • Synthesis and application of epoxy resin based on catechuic acid
  • Synthesis and application of epoxy resin based on catechuic acid
  • Synthesis and application of epoxy resin based on catechuic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] The synthesis of embodiment 1 protocatechuic acid epoxy monomer

[0052] Under the protection of nitrogen gas, add magneton, 100mmol protocatechuic acid and 94mL epichlorohydrin to a 250ml dry three-necked bottle. Then 5 mmol of triethylbenzylammonium chloride was added. Raise the temperature to 100°C and react for 2 hours, cool to room temperature, add 120 mL of 20 wt% sodium hydroxide aqueous solution, react at room temperature for 2 hours, add water to wash, extract with ethyl acetate several times, dry with anhydrous sodium sulfate, concentrate, and column chromatography to obtain the target 6.4 g of a colorless oily epoxy compound monomer.

[0053] 1 H NMR (400MHz, DMSO-d 6 )δ7.62(dd, J=8.4,2.0Hz,1H),7.52(d,J=2.1Hz,1H),7.14(d,J=8.6Hz,1H),4.61(dd,J=12.4,2.7 Hz,1H),4.50–4.39(m,2H),4.06(dd,J=12.4,6.4Hz,1H),3.92(dddd,J=21.9,11.4,6.6,1.8Hz,2H),3.39(dqd, J=7.9,4.0,2.2Hz,3H),2.90–2.81(m,3H),2.74(ddt,J=7.3,5.0,2.7Hz,3H). 13 C NMR (101MHz, CDCl 3 )δ165.71, 152.74, 14...

Embodiment 2

[0054] The synthesis of embodiment 2 protocatechuic acid epoxy monomer

[0055] The experimental method was the same as that in Example 1, except that tetraethylammonium chloride was used instead of triethylbenzylammonium chloride, and 5.2 g of the target monomer was obtained by column chromatography.

Embodiment 3

[0056] The synthesis of embodiment 3 protocatechuic acid epoxy monomer

[0057] The experimental method was the same as that in Example 1, except that tetrabutylammonium chloride was used instead of triethylbenzylammonium chloride, and 5.1 g of the target monomer was obtained by column chromatography.

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Abstract

The invention provides synthesis and application of epoxy resin based on catechuic acid, and particularly provides a catechuic acid epoxidation monomer. The catechuic acid epoxidation monomer has a structure represented by formula I in the specification. The monomer can be cured to form catechuic acid epoxy resin, so that the catechuic acid epoxy resin is used for preparing aerospace special materials.

Description

technical field [0001] The invention relates to the technical field of high-performance polymer production, in particular to a method for preparing epoxy resin with high glass transition temperature starting from protocatechuic acid, a fermentation product of glucose. Background technique [0002] Epoxy resin, as a thermosetting resin, achieved its first commercial application in 1947 as a surface coating. Due to the wide selection of curing agents, from alkylamines, alcohols, mercaptans to aromatic amines, phenols, etc., the cured epoxy resin has a wide range of adjustable thermodynamics and mechanical properties. Therefore, it means that epoxy resin has the potential to be used in different application scenarios. Currently, epoxy resins are commonly used as base resins, adhesives, and surface coatings, as well as in aerospace applications. The largest proportion of its application is still surface coatings. In addition, composite materials prepared by epoxy resin doped ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G59/32C07D301/28C07D301/30C07D303/30
CPCC07D301/28C07D301/30C07D303/30C08G59/3218
Inventor 房强陈星融王钦宏孙晶顾群侯加仁高俊飞方林玄
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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