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Bio-acrylic acid ester based on schiff base structure and preparation method and application thereof

A bio-based acrylate and Schiff base technology, applied in the preparation of imino compounds, organic chemistry, coatings, etc., to achieve the effects of good controllability, easy implementation, high glass transition temperature and heat distortion temperature

Inactive Publication Date: 2017-07-04
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

So far, there is no patent report on utilizing vanillin to prepare acrylate monomer by Schiff base reaction in the prior art

Method used

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  • Bio-acrylic acid ester based on schiff base structure and preparation method and application thereof
  • Bio-acrylic acid ester based on schiff base structure and preparation method and application thereof
  • Bio-acrylic acid ester based on schiff base structure and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] (1) Dissolve 10g of vanillin and 1.8g of ethylenediamine in 15ml of tetrahydrofuran, react at 10°C for 72 hours, cool to room temperature to precipitate a yellow precipitate, filter it with suction, wash with a small amount of ethanol, and dry it to obtain vanillin ethylenediamine Amine Schiff base. The structural formula is shown in the following formula II-1, and the yield is 95%. 1 H-NMR such as figure 1 As shown, there is a one-to-one correspondence between each peak on the figure and the hydrogen above the structure of formula II-1.

[0032]

[0033] (2) Dissolve 10 g of vanillin ethylenediamine Schiff base and 12.3 g of acryloyl chloride in 7 ml of butyl acetate, and stir with a magnet. Subsequently, 0.48g of triethylamine was dissolved in 7ml of butyl acetate, and added dropwise through a constant pressure separatory funnel. After 1h, the temperature was raised to 10°C for 70h. After the reaction is complete, add 10ml of sodium bicarbonate aqueous solution ...

Embodiment 2

[0036] (1) Dissolve 10g of vanillin and 1.4g of butanediamine in 30ml of tetrahydrofuran, react at 20°C for 60h, cool to room temperature to precipitate a yellow precipitate, filter with suction, wash with a small amount of ethanol, and dry it to obtain butanediamine mat husband base. The structural formula is shown in the following formula II-2, and the yield is 92%.

[0037]

[0038] (2) Dissolve 10g of Schiff's base and 20.5g of acryloyl chloride in 15ml of ethanol, and stir with a magnet. Subsequently, 0.8 g of triethylamine was dissolved in 15 ml of ethanol, and added dropwise through a constant pressure separatory funnel. After 1 hour, the temperature was raised to 20° C. for 65 hours. After the reaction is complete, add 20ml 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 three times to remove acrylic acid and triethylamine, and then distill...

Embodiment 3

[0041] (1) Dissolve 10g of vanillin and 0.76g of hexamethylenediamine in 50ml of tetrahydrofuran, react at 30°C for 50h, cool to room temperature to precipitate a yellow precipitate, filter with suction, wash with a small amount of ethanol, and dry it to obtain hexamethylenediamine mat husband base. The structural formula is shown in the following formula II-3, and the yield is 91%.

[0042]

[0043] (2) Dissolve 10 g of hexamethylenediamine Schiff base and 44.9 g of acryloyl chloride in 25 ml of tetrahydrofuran, and stir with a magnet. Subsequently, 0.86 g of triethylamine was dissolved in 25 ml of tetrahydrofuran, and added dropwise through a constant pressure separatory funnel. After 1 hour, 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 funnel and wash with water three times to r...

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Abstract

The invention discloses a bio-acrylic acid ester based on a schiff base structure, the structure is shown as a formula I, in the formula, R<1> is one of C2H4, C4H8, C6H4, C6H12, C8H16, C10H20, and C13H10, and R<2> is hydrogen or methyl. The invention also discloses a preparation method of bio-acrylic acid ester, and an application of the bio-acrylic acid ester in the field of a paint, the process is simple, industrialization production is easy, the prepared product has better excellent mechanical properties and hear resistance, the bio-acrylic acid ester has high glass-transition temperature and thermal deformation temperature and degradation performance, and can be used for the fields of the paint, an adhesive and aviation spaceflight.

Description

technical field [0001] The invention relates to the field of bio-based polymer materials, in particular to a bio-based acrylate based on a Schiff base structure, a preparation method and an application in the field of coatings. Background technique [0002] Over the past century, due to the vigorous development of the petrochemical industry, the application of petroleum products has become increasingly widespread. Various products and their derivatives produced by petroleum have brought great convenience to people's life and production, and promoted the development of society and the progress of human civilization, but at the same time, various environmental problems cannot be ignored. . At the same time, petroleum resources are an unsustainable and non-renewable resource. With the increasing depletion of its reserves, the cost of polymer materials derived from petroleum will inevitably increase. Recently, under the pressure of protecting the environment, reducing producti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C249/02C07C251/24C09D4/02
CPCC07C249/02C07C251/24C09D4/00
Inventor 王胜马松琪代金月沈潇斌韦静静刘小青朱锦
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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