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Bio-based epoxy resin based on natural amino acids, and preparation method and application thereof

A technology of natural amino acid and epoxy resin, applied in the direction of organic chemistry, etc., to achieve the effect of saving petroleum resources, good controllability and simple process

Inactive Publication Date: 2019-02-26
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

At present, there is no report on the preparation of epoxy resins with natural amino acids

Method used

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  • Bio-based epoxy resin based on natural amino acids, and preparation method and application thereof
  • Bio-based epoxy resin based on natural amino acids, and preparation method and application thereof
  • Bio-based epoxy resin based on natural amino acids, and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0038] Dissolve 1 mol of alanine, 1.2 mol of vanillin, and 1 mol of KOH in 250 mL of ethanol, react at 30°C for 24 hours, add 3 mol of sodium borohydride and control the reaction temperature at 10°C, at this temperature The reaction was continued for 36 hours to finally obtain the alanine-vanillin multifunctional monomer with a yield of 89%.

[0039] React 1 mol of alanine-vanillin multifunctional monomer and 5 mol of epichlorohydrin in the presence of 0.1 mol of tetrabutylammonium bromide at 100°C for 2 hours, then remove the solvent by rotary evaporation under reduced pressure, wash with water And after drying, the epoxidized alanine-vanillin compound was obtained with a yield of 93%. H NMR spectrum 1 H-NMR such as figure 1 As shown, each peak on the figure is in one-to-one correspondence with the hydrogen atoms on the epoxidized alanine-vanillin dicyanide compound structure.

[0040]Mix the obtained epoxidized alanine-vanillin compound and curing agent DDS in acetone acc...

Embodiment 2

[0042] Dissolve 1 mol of lysine, 2.5 mol of vanillin, and 1.1 mol of KOH in 200 mL of ethanol, react at 50°C for 16 hours, add 4 mol of sodium borohydride and control the reaction temperature at 20°C, at this temperature The reaction was continued for 24 hours to finally obtain a lysine-vanillin multifunctional monomer with a yield of 81%.

[0043] React 1mol lysine-vanillin multifunctional monomer and 8mol epichlorohydrin in the presence of 0.15mol tetrabutylammonium bromide at 80°C for 5 hours, then remove the solvent by rotary evaporation under reduced pressure, wash with water And after drying, the epoxidized lysine-vanillin compound was obtained with a yield of 91%. H NMR spectrum 1 H-NMR such as figure 2 As shown, each peak on the figure is in one-to-one correspondence with the hydrogen atoms on the epoxidized lysine-vanillin dicyanide compound structure.

[0044] Mix the obtained epoxidized lysine-vanillin compound and the curing agent DDS in acetone according to th...

Embodiment 3

[0046] Dissolve 1 mol of tyrosine, 1.5 mol of vanillin, and 1.5 mol of KOH in 180 mL of ethanol, react at 80°C for 12 hours, add 2 mol of sodium borohydride and control the reaction temperature at 30°C, at this temperature The reaction was continued for 12 hours to finally obtain a tyrosine-vanillin multifunctional monomer with a yield of 79%.

[0047] React 1mol tyrosine-vanillin multifunctional monomer and 12mol epichlorohydrin in the presence of 0.2mol tetrabutylammonium bromide at 70°C for 8 hours, then remove the solvent by rotary evaporation under reduced pressure, wash with water And after drying, the epoxidized tyrosine-vanillin compound was obtained with a yield of 87%.

[0048] Mix the obtained epoxidized tyrosine-vanillin compound and the curing agent DDS in acetone according to the molar ratio of epoxy and NH one to one, then heat and pre-cure in a blast oven, and finally carry out at 180°C After curing for 2 hours, a cured product of tyrosine-vanillin-DDS epoxy r...

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Abstract

The invention discloses a bio-based epoxy resin based on a natural amino acid compound. The structural formula of the bio-based epoxy resin comprises natural amino acids and an aldehyde group compound. The invention also discloses a preparation method for the above bio-based epoxy resin. The preparation method comprises the following steps: subjecting natural amino acid monomers and the aldehyde group compound to a condensation reaction in an alkaline ethanol environment under heating; subjecting bio-based Schiff base polyfunctional monomers obtained in the previous step and sodium borohydrideto a reduction reaction in an ethanol solution; and subjecting bio-based polyfunctional monomers to an epoxidation reaction in an epichlorohydrin solution to prepare the bio-based epoxy resin. The preparation method provided by the invention is simple in process flow, easy and convenient to operate, good in controllability, easy to implement and suitable for large-scale industrial production. Thermosetting epoxy resin prepared from the bio-based epoxy resin based on the natural amino acid compound and an amine or acid anhydride curing agent in the invention has excellent thermal properties and mechanical properties, and is possible to replace conventional petroleum-based products.

Description

technical field [0001] The invention belongs to the technical field of thermosetting epoxy resins, in particular to bio-based epoxy resins based on natural amino acids and their preparation methods and applications. Background technique [0002] Epoxy resin refers to the general term for a class of polymers containing two or more epoxy groups in the molecular structure. It is the polycondensation product of epichlorohydrin and bisphenol A or other polyols. Due to the high chemical activity of the epoxy group in its structure, it can react with a variety of compounds containing active hydrogen, thereby curing and crosslinking to form a network structure, so it is a thermosetting resin. Epoxy resin is a general-purpose thermosetting resin with a very wide range of uses. It is widely used in aerospace, coatings, adhesives, circuit packaging and other fields because of its excellent comprehensive properties. It is a very important class of polymer materials. . However, at thi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D301/28C07D301/30C07D303/23C07D405/12C08G59/28
CPCC07D301/28C07D301/30C07D303/23C07D405/12C08G59/28
Inventor 代金月刘小青腾娜朱锦
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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