Vanillin-based low-viscosity bio-based epoxy resin and preparation method thereof

A technology based on epoxy resin and vanillin, which is applied in the field of low-viscosity bio-based epoxy resin and its preparation, can solve problems such as difficult application, poor resin processing performance, and unstable performance, and achieve low-viscosity thermodynamic properties and reaction process Simple, low toxicity, and good industrial application value

Active Publication Date: 2020-02-25
CHANGCHUN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the large and complex molecular structure of lignin, the resin directly obtained from it has poor processability, unstable performance, and is difficult to apply

Method used

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  • Vanillin-based low-viscosity bio-based epoxy resin and preparation method thereof
  • Vanillin-based low-viscosity bio-based epoxy resin and preparation method thereof
  • Vanillin-based low-viscosity bio-based epoxy resin and preparation method thereof

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preparation example Construction

[0034] The present invention also provides a kind of preparation method of low-viscosity bio-based epoxy resin based on vanillin, comprising the following steps:

[0035] Step 1. Under nitrogen protection, add solvent, glycerin, itaconic acid and methanesulfonic acid into the reaction vessel, and then react at 140-160°C for 5-10 hours. The molar ratio of glycerol to itaconic acid is preferably 1:3-5, the quality of catalyzer methanesulfonic acid is 0.15wt%; The selected solvent is preferably toluene, and reaction route is as follows:

[0036]

[0037] Step 2: Add product 1, solvent and DMF to the reaction vessel and place it in an ice-water bath at 0°C for stirring. The stirring rate is preferably 300-400r / min, then drop in oxalyl chloride, slowly heat the reaction mixture and set it at 20- React at 70°C for 3-5 hours until the solid is completely dissolved, and then rotate the obtained solution preferably at 40-60°C to obtain product 2; the molar ratio of the product 1 to ...

Embodiment 1

[0046] Step 1. Add 0.3mol powdered itaconic acid, 0.1mol glycerin, 50ml toluene, and 5wt% catalyst methanesulfonic acid into a three-neck round bottom flask, one of which is equipped with a stirrer and the other for nitrogen flow, a third neck toluene reflux and azeotropic distillation apparatus, the internal temperature was set to 150 °C and the reaction was continued for 10 hours. From toluene, gradually extract the condensed release water (1.5mol); Anhydrous toluene is continuously refluxed in the reactor to obtain product 1; the nuclear magnetic spectrum is as figure 2 shown.

[0047] Step 2. Add the mixture of product 1 (0.1mol), THF (100ml) and DMF (catalyst, 0.05ml) to a round-bottomed flask, and add oxalyl chloride (0.3mol) drop by drop within 20min in an ice-water bath at 0°C . The reaction mixture was slowly heated and reacted at 50 °C for 4 hours until the solid was completely dissolved. The resulting solution was then rotatably steamed to obtain product 2;

[...

Embodiment 2

[0059] Step 1. Add 0.5mol powdered itaconic acid, 0.1mol glycerol, 50ml toluene, and 5wt% catalyst methanesulfonic acid into a three-neck round bottom flask, one of which is equipped with a stirrer and the other for nitrogen flow, a third neck toluene reflux and azeotropic distillation apparatus, set the internal temperature to 160 °C and continue the reaction for 5 hours. Condensed liberated water (1.5 mol) was gradually extracted from toluene; anhydrous toluene was continuously refluxed into the reactor to obtain product 1;

[0060] Step 2. Add the mixture of product 1 (0.1mol), THF (100ml) and DMF (catalyst, 0.05ml) to a round-bottomed flask, and add oxalyl chloride (0.4mol) drop by drop within 20min in an ice-water bath at 0°C . The reaction mixture was slowly heated and reacted at 25°C for 4 hours until the solid was completely dissolved. The resulting solution was then rotatably steamed to obtain product 2;

[0061] Step 3, add product 2 (0.1mol) into 100ml ethyl acet...

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Abstract

The invention provides a vanillin-based low-viscosity bio-based epoxy resin and a preparation method thereof, and belongs to the field of epoxy resins. The epoxy resin has a structure represented by formula (1). The invention also provides a preparation method of the vanillin-based low-viscosity bio-based epoxy resin. The structure is a dendritic molecular structure, so the space free volume is increased, the viscosity of a bio-based epoxy resin monomer is reduced, and the processability of the resin is improved; and the quantity o epoxy groups in the epoxy monomer is large, so that the crosslinking density of the epoxy resin is improved, and the aromatic structure is also beneficial to the improvement of the thermal stability and mechanical properties of the material. The main raw materials are from renewable resources, so the preparation method has the advantages of low price, environmental friendliness, energy saving, simplicity and low toxicity in the whole reaction process, and noharsh reaction condition; and the bio-based epoxy resin has low viscosity, excellent thermodynamic properties and excellent mechanical properties, so the bio-based epoxy resin has excellent industrial application values.

Description

technical field [0001] The invention belongs to the field of epoxy resins, and in particular relates to a low-viscosity bio-based epoxy resin based on vanillin and a preparation method thereof. Background technique [0002] Epoxy resin is a polymer oligomer that contains two or more epoxy groups, has aliphatic or aromatic backbone, and can react with other active groups to form thermosetting products. Epoxy resin has a large number of active and polar groups. As a thermosetting resin, epoxy resin has excellent comprehensive properties, good adhesion, excellent mechanical properties, small curing shrinkage, good manufacturability, and excellent Electrical insulation and corrosion resistance are widely used in coatings, composite materials, adhesives, electronic packaging materials, engineering plastics, civil engineering materials and other fields. [0003] However, at this stage, most epoxy resins are derived from petroleum resources, especially bisphenol A epoxy resin, and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G59/06C08G59/02C07D301/28C07D303/24
CPCC08G59/063C08G59/027C07D303/24C07D301/28
Inventor 敖玉辉郭宗伟尚垒庄海林刘浏杜巍峰迟至远
Owner CHANGCHUN UNIV OF TECH
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