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A kind of furyl glycidyl ether and its synthesis method and application

A technology of glycidyl ether and synthesis method, applied in the direction of organic chemistry, etc., can solve problems such as easy cracks, brittleness, and large internal stress

Active Publication Date: 2018-02-23
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] Due to the rigidity of the benzene ring, the internal stress of the bisphenol A type epoxy resin is large, brittle, and prone to cracks after curing, which limits its application in certain technical fields. In practical applications, bisphenol A type epoxy resin Resins often require toughening modification, and furan-type epoxy resins with similar structures also have similar problems
However, the above-mentioned applications and studies have not discussed and solved this problem.

Method used

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  • A kind of furyl glycidyl ether and its synthesis method and application
  • A kind of furyl glycidyl ether and its synthesis method and application
  • A kind of furyl glycidyl ether and its synthesis method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0049] (1) Mix 100g of maleic anhydride, 1000g of dichloromethane, and 100g of n-hexylamine evenly, react at 30°C for 8 hours, add 150g of oxalyl chloride dropwise to the reaction solution, react at 30°C for 168 hours, and finally in the reaction solution 150g of triethylamine was added dropwise, reacted at 30°C for 24 hours, extracted three times with dichloromethane, washed with saturated brine three times, dried, and dichloromethane was distilled off under reduced pressure to obtain N-hexylmaleimide;

[0050] The proton nuclear magnetic resonance spectrum of the N-hexylmaleimide that prepares is as figure 2 shown;

[0051] (2) 100g N-hexylmaleimide, 500g chloroform and 150g furandimethanol glycidyl ether were reacted at 30°C for 24 hours, and the chloroform was removed by distillation under reduced pressure to obtain the formula (I) The furyl glycidyl ether shown, wherein the R group is n-hexyl.

[0052] The yield of the product was 70%, and the epoxy value of the product ...

Embodiment 2

[0055] (1) Mix 100g maleic anhydride, 1000g dichloromethane, and 100g n-hexylamine evenly, react at 40°C for 6 hours, add 200g of oxalyl chloride dropwise to the reaction solution, react at 40°C for 120 hours, and finally in the reaction solution 200g of triethylamine was added dropwise, reacted at 40°C for 24 hours, extracted three times with dichloromethane, washed with saturated brine three times, dried, and dichloromethane was distilled off under reduced pressure to obtain N-hexylmaleimide;

[0056] (2) 100g N-hexylmaleimide, 500g chloroform and 150g furandimethanol glycidyl ether were reacted at 30°C for 24 hours, and the chloroform was removed by distillation under reduced pressure to obtain the formula (I) The furyl glycidyl ether shown, wherein the R group is n-hexyl.

[0057] The yield of the product was 58%, and the epoxy value of the product was 0.46 (theoretical epoxy value was 0.475).

Embodiment 3

[0059] (1) Mix 100g maleic anhydride, 700g acetone, and 150g n-decylamine evenly, react at 40°C for 8 hours, add 100g of acetyl chloride dropwise to the reaction solution, react at 40°C for 240 hours, and finally drop in the reaction solution Add 150g of acetic anhydride, react at 40°C for 50 hours, obtain N-decylmaleimide after extraction, washing with water, drying, and distillation under reduced pressure to remove the solvent;

[0060] (2) 100g N-decylmaleimide, 300g ethyl acetate and 100g furandimethanol glycidyl ether were reacted at 50°C for 24 hours, and the ethyl acetate was distilled off under reduced pressure to obtain formula (I) Shown furyl glycidyl ether, wherein the R group is n-decyl.

[0061] The yield of the product was 55%, and the epoxy value of the product was 0.41 (theoretical epoxy value was 0.419).

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Abstract

The invention discloses furyl glycidyl ether of which the structural formula (I) is as shown in the specification. In the formula (I), R is C1-C2 alkyl or as shown in formula (II); and in the formula (II), n is 1-10, and R1 is H, methyl or ethyl. The invention further discloses a preparation method of the furyl glycidyl ether. The furyl glycidyl ether has a long-chain structure, so that epoxy resin has excellent toughness; Diels-Alder reaction of furan and maleimide has thermal reversibility, the toughness of the epoxy resin can be adjusted through thermal treatment, and the furyl glycidyl ether can be applied to toughness improvement on the epoxy resin.

Description

technical field [0001] The invention relates to a bio-based epoxy resin, in particular to a furyl glycidyl ether, a synthesis method and an application thereof. Background technique [0002] Epoxy resin is one of the most widely used thermosetting resins. At present, the global annual output is about 2 million tons, of which bisphenol A epoxy resin accounts for more than 85%. Bisphenol A epoxy resin is mainly made from bisphenol A and epichlorohydrin. However, studies have shown that bisphenol A, which accounts for more than 67% of the molecular weight of bisphenol A epoxy resin, can stimulate the growth of estrogen receptor protein, damage the androgen receptor protein, and threaten human health. Therefore, European and American countries have gradually introduced relevant laws and regulations to prohibit the use of bisphenol A in children's containers, food and beverage containers, etc. Moreover, as environmental problems and energy problems become increasingly prominent...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/18C08G59/32
CPCC07D491/18C08G59/3245
Inventor 沈潇斌刘小青马松琪朱锦
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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