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Imine-bond-containing epoxy resin monomer, and preparation method and application thereof

An epoxy resin and imine bond-containing technology, applied in organic chemistry and other directions, can solve the problems of difficult recycling of thermosetting epoxy resins, and achieve the effects of excellent heat resistance and mechanical properties, good manufacturability, and wide application prospects.

Active Publication Date: 2019-10-29
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is to provide an epoxy resin monomer containing an imine bond and its preparation method and application, which solves the problem that the existing thermosetting epoxy resin is difficult to recycle

Method used

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  • Imine-bond-containing epoxy resin monomer, and preparation method and application thereof
  • Imine-bond-containing epoxy resin monomer, and preparation method and application thereof
  • Imine-bond-containing epoxy resin monomer, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Add 35.6g of aldehyde group-containing epoxy compound 2 and 80mL of anhydrous methanol into a container at room temperature, and stir evenly to obtain a transparent solution. 17.0g Alkanediamine was dissolved in 60mL of anhydrous methanol, and placed in a constant pressure dropping funnel, slowly added dropwise to the above-mentioned aldehyde group-containing epoxy compound 2 solution at room temperature and under rapid stirring conditions, after the dropwise addition, heated to React at 60°C for 4 hours. After the reaction is over, distill off the anhydrous methanol solvent under reduced pressure to obtain an epoxy resin monomer containing an imine bond. The structure is as follows:

[0044]

[0045] Characterization of monomer structure, viscosity and epoxy equivalent of epoxy resin containing imine bond:

[0046] Infrared spectrum (potassium bromide tablet): 1635cm -1 (-CH=N-), 1608cm -1 and 1512cm -1 (benzene ring), 910cm -1 (epoxy).

[0047] 1 HNMR (DMSO-d...

Embodiment 2

[0059] Add 41.6g of aldehyde group-containing epoxy compound 1 and 80mL of absolute ethanol into a container at room temperature, and stir evenly to obtain a transparent solution. Dissolve 17.0g of isophoronediamine in 80mL of absolute ethanol, and place it in a constant pressure dropping funnel, slowly add it dropwise to the above-mentioned aldehyde group-containing epoxy compound 1 solution at room temperature and under rapid stirring conditions, drop After the addition, heat to 40°C to react for 10 hours. After the reaction, distill off the absolute ethanol solvent under reduced pressure to obtain an epoxy resin monomer containing an imine bond. The structure is as follows:

[0060]

[0061] Characterization of monomer structure, viscosity and epoxy equivalent of epoxy resin containing imine bond:

[0062] Infrared spectrum (potassium bromide tablet): 1633cm -1 (-CH=N-), 1606cm -1 and 1510cm -1 (benzene ring), 912cm -1 (epoxy).

[0063] 1 HNMR (DMSO-d6, ppmδ): 8.6-...

Embodiment 3

[0074] Add 35.6g of aldehyde group-containing epoxy compound 2 and 70mL of tetrahydrofuran into a container at room temperature, and stir evenly to obtain a transparent solution. Dissolve 17.0g of methylcyclohexanediamine in 70mL of tetrahydrofuran, place it in a constant pressure dropping funnel, and slowly add it dropwise to the above-mentioned aldehyde group-containing epoxy compound 2 solution at room temperature and under rapid stirring conditions, and the addition ends Afterwards, it was heated to 50°C for 6 hours. After the reaction, the anhydrous ethanol solvent was distilled off under reduced pressure to obtain an epoxy resin monomer containing an imine bond. The structure is as follows:

[0075]

[0076] Characterization of monomer structure, viscosity and epoxy equivalent of epoxy resin containing imine bond:

[0077] Infrared spectrum (potassium bromide tablet): 1636cm -1 (-CH=N-), 1595cm -1 and 1506cm -1 (benzene ring), 908cm -1 (epoxy).

[0078] 1 HNMR (...

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Abstract

The invention relates to an imine-bond-containing epoxy resin monomer, and a preparation method and an application thereof. The imine-bond-containing epoxy resin monomer is prepared from an aldehyde group containing epoxy compound and organic diamine through a Schiff base reaction. The imine-bond-containing epoxy resin monomer provided by the invention is in a liquid state at a normal temperatureand has good process performances; the imine-bond-containing epoxy resin prepared by using a method provided by the invention has excellent heat resistance and mechanical properties and can be subjected to repeated processing molding by hot-press treatment, and the retention rates of thermal properties and mechanical properties of repeatedly-molded epoxy resin are higher than 90%; in addition, theimine-bond-containing epoxy resin monomer can be degraded in an amine solvent, solves the problem of difficult recycling of conventional thermosetting epoxy resin, and has extensive application prospects.

Description

technical field [0001] The invention belongs to the field of epoxy resins, in particular to an epoxy resin monomer containing an imine bond, a preparation method and application thereof. Background technique [0002] Epoxy resin is one of the three general-purpose thermosetting resins. It is widely used in adhesives, coatings, and electronic packaging because of its good bonding performance, dimensional stability, mechanical strength, chemical corrosion resistance, and process performance. , advanced composite materials and other fields. However, traditional epoxy resins have a highly cross-linked structure constructed of irreversible covalent bonds, and their internal molecular topology is almost unchangeable, showing insoluble and infusible properties macroscopically. Therefore, once the traditional epoxy resin products are cured, it is difficult to recycle them, and the increasing amount of epoxy resin waste every year brings challenges to the protection of the ecologica...

Claims

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Application Information

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IPC IPC(8): C07D303/27C07D303/24C08G59/24C08G59/28
CPCC07D303/27C07D303/24C08G59/245C08G59/28Y02W30/62
Inventor 刘万双刘海洋高家蕊魏毅
Owner DONGHUA UNIV
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