Three kinds of bio-based epoxy resins based on furan ring structure and their preparation methods and applications

A technology based on epoxy resin and furan ring, which is applied in the field of bio-based polymer materials, can solve the problems of poor heat resistance of materials, influence on material preparation, and decrease in mechanical properties of materials, and achieve the effects of reducing pollution, easy implementation and simple operation.

Active Publication Date: 2018-01-02
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The compound with furan ring can prepare epoxy resin through Diels-Alder reaction (US Patent, US6337384B1), but due to the reversibility of Diels-Alder reaction, the epoxy resin prepared by Diels-Alder reaction will be about 120 ℃. The reverse Diels-Alder reaction occurs, which leads to poor heat resistance of the material. At the same time, the reverse Diels-Alder reaction also occurs when the epoxy resin is cured, which affects the preparation of the material and leads to a decrease in the mechanical properties of the material.

Method used

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  • Three kinds of bio-based epoxy resins based on furan ring structure and their preparation methods and applications
  • Three kinds of bio-based epoxy resins based on furan ring structure and their preparation methods and applications
  • Three kinds of bio-based epoxy resins based on furan ring structure and their preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] (1) Dissolve 10g of maleic anhydride and 4.8g of methanolamine in 10ml of tetrahydrofuran, react at 10°C for 72h, cool to room temperature overnight to precipitate a white precipitate, filter it with suction, wash with a small amount of ethanol, and dry it to obtain N-hydroxy Methylmaleimide. Then furan and N-methylolmaleimide were stirred at room temperature for 24h to obtain furan N-hydroxymethylmaleimide.

[0050](2) Dissolve 10 g of furan N-methylol maleimide and 4.3 g of acryloyl chloride in 5 ml of butyl acetate, and stir with a magnet. Subsequently, 0.48 g of triethylamine was dissolved in 5 ml of butyl acetate, and added dropwise through a constant pressure separatory funnel for 1 hour, and then the temperature was raised to 10° C. for 72 hours. After the reaction is complete, add 10ml of sodium bicarbonate aqueous solution and stir for half an hour to remove excess acryloyl chloride, then pour the mixed solution into a separatory funnel and wash with water thr...

Embodiment 2

[0055] (1) Dissolve 10g of maleic anhydride and 14.4g of ethanolamine in 30ml of dioxane, react at 20°C for 65h, cool to room temperature overnight to precipitate a white precipitate, filter with suction, wash with a small amount of ethanol, and dry it to obtain N -Hydroxyethylmaleimide, 1 H-NMR such as image 3 As shown, each peak on the figure is in one-to-one correspondence with the hydrogen atoms on the N-hydroxyethylmaleimide structure, 13 C-NMR such as Figure 4 As shown, each peak on the figure corresponds to the carbon atom above the N-hydroxyethylmaleimide structure. Then furan and N-hydroxyethylmaleimide were stirred at room temperature for 24h to obtain furan N-hydroxyethylmaleimide.

[0056] (2) Dissolve 10 g of furan N-hydroxyethylmaleimide and 12.9 g of acryloyl chloride in 15 ml of ethanol, and stir with a magnet. Subsequently, 4.8 g of triethylamine was dissolved in 15 ml of ethanol, and added dropwise through a constant pressure separatory funnel for 1 hou...

Embodiment 3

[0061] (1) Dissolve 10g of maleic anhydride and 24g of ethanolamine in 50ml of ether, react at 30°C for 55h, cool to room temperature overnight to precipitate a white precipitate, filter it with suction, wash with a small amount of ethanol, and dry it to obtain N-hydroxypropyl maleimide. Then furan and N-hydroxypropylmaleimide were stirred at room temperature for 24h to obtain furan N-hydroxypropylmaleimide.

[0062] (2) Dissolve 10 g of furan N-hydroxypropylmaleimide and 21.5 g of acryloyl chloride in 25 ml of tetrahydrofuran, and stir with a magnet. Subsequently, 14.4 g of triethylamine was dissolved in 25 ml of tetrahydrofuran, added dropwise through a constant pressure separatory funnel, and the drop was completed in 1 hour, and then the temperature was raised to 30° C. for 55 hours. After the reaction is complete, add 30ml of sodium bicarbonate aqueous solution and stir for half an hour to remove excess acryloyl chloride, then pour the mixed solution into a separatory fu...

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Abstract

The invention discloses three types of bio-based epoxy resin with furan ring structures. The structures are represented as a formula I, a formula II and a formula III respectively, and in the formulae, R1, R2 and R3 are independently selected from at least one of CH2, C2H4, C3H6, C4H8, C5H10, C6H12, C7H14, C8H16 and C9H18. The invention further discloses a preparation method of the bio-based epoxy resin. The process is simple, industrial production is facilitated, and a product prepared with the method has excellent mechanical property and heat resistance, has higher glass-transition temperature and heat deflection temperature and can be applied to the fields of paint, adhesives and aerospace.

Description

technical field [0001] The invention relates to the field of bio-based polymer materials, in particular to three bio-based epoxy resins based on a furan ring structure, a preparation method and an application in the field of coatings. Background technique [0002] Epoxy resins are widely used in various fields such as aerospace, construction and transportation, and electronic appliances because of their excellent mechanical properties, thermal properties, and corrosion resistance. However, commonly used epoxy resins generally use petroleum-based compounds such as bisphenol A or bisphenol F as raw materials, because they contain structural units such as aromatic benzene rings, which will cause poor aging resistance and UV resistance. [0003] In addition, as petroleum resources are increasingly depleted, finding sustainable, high-quality, and cheap petroleum substitutes is the key to the existence and development of the polymer industry. Bio-based polymer materials use renew...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G59/26C08G59/32C07D491/22C09D163/00C09J163/00
CPCC07D491/22C08G59/26C08G59/3236C09D163/00C09J163/00
Inventor 王胜马松琪代金月沈潇斌李鹏刘小青朱锦
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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