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Malic acid radical water-borne epoxy resin and preparation method thereof

A water-based epoxy resin, malic acid-based technology, applied in organic chemistry and other directions, can solve unseen problems and achieve the effect of saving resources, good glass transition temperature, and broad application prospects

Active Publication Date: 2013-12-11
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] So far, there are no literature and patent reports that directly utilize malic acid to synthesize epoxy resin in the prior art

Method used

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  • Malic acid radical water-borne epoxy resin and preparation method thereof
  • Malic acid radical water-borne epoxy resin and preparation method thereof
  • Malic acid radical water-borne epoxy resin and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] 1) Mix 100g malic acid, 1200g dioxane, 800g allyl chloride and 60g sodium hydroxide, react at 80°C for 8 hours, filter, wash with water, distill under reduced pressure to remove solvent, water, etc. to obtain diallyl malate base ester.

[0034] The diallyl malate of 1 H NMR spectrum as figure 1 as shown, figure 1 The appearance of 5.88-5.97ppm and 5.18-5.37ppm in the middle represents the H on the allyl double bond, about 4.57-4.66ppm represents the H added to the methylene adjacent to the double bond on the allyl group, and 2.84ppm represents - The H on OH, and other peaks are consistent with the H proton shift of diallyl malate, which proves that the obtained diallyl malate has the structure of formula II.

[0035]

[0036] 2) Mix 100g of diallyl malate prepared above, 30g of hydrogen peroxide, 20g of formic acid, 5g of Amberlite-120 (Amberlite series ion exchange resin produced by Rohm and Haas Company) and 50g of dioxane at 60 After reacting at ℃ for 60 hours...

Embodiment 2

[0041] 1) Mix 100g malic acid, 900g tetrahydrofuran, 400g allyl chloride and 400g potassium carbonate, react at 40°C for 72 hours, filter, wash with water, distill under reduced pressure to remove solvent, water, etc. to obtain diallyl malate.

[0042] According to the diallyl malate 1The H NMR spectrum shows that 5.88-5.97ppm and 5.18-5.37ppm in the figure represent the H on the allyl double bond, and about 4.57-4.66ppm represents the methylene adjacent to the double bond on the allyl plus H, 2.84ppm represents the H on the -OH, and other peaks are consistent with the H proton displacement of diallyl malate, which proves that the obtained diallyl malate has the structure of formula II.

[0043]

[0044] 2) Mix 100g of diallyl malate prepared above, 700g of m-chloroperoxybenzoic acid and 2500g of dichloromethane, react at 25°C for 200 hours, then wash 5 times with 5% sodium sulfite aqueous solution, and then Wash with 15% sodium carbonate aqueous solution for 5 times, then...

Embodiment 3

[0049] 1) Mix 100g malic acid, 100g dimethyl sulfoxide, 300g allyl bromide and 300g 1,8-diazabicyclo[5.4.0]undec-7-ene, react at 0℃ for 0.5 hours, Filtrate, wash with water, and distill off the solvent and water under reduced pressure to obtain diallyl malate.

[0050] According to the diallyl malate 1 The H NMR spectrum shows that 5.88-5.97ppm and 5.18-5.37ppm in the figure represent the H on the allyl double bond, and about 4.57-4.66ppm represents the methylene adjacent to the double bond on the allyl plus H, 2.84ppm represents the H on the -OH, and other peaks are consistent with the H proton displacement of diallyl malate, which proves that the obtained diallyl malate has the structure of formula II.

[0051]

[0052] 2) Mix 100g of diallyl malate prepared above, 400g of hydrogen peroxide, 120g of formic acid, 180g of sulfuric acid and 900g of butanone, react at 70°C for 10 hours, and then wash with 20% by mass aqueous solution of sodium dithionite 1 time, then wash w...

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Abstract

The invention discloses malic acid radical water-borne epoxy resin (shown in a formula I) and a preparation method thereof. The preparation method of the malic acid radical water-borne epoxy resin comprises the following steps: firstly, an malic acid and an allyl reagent react through dehydrohalogenation under the condition that an acid-binding agent exists to obtain malic acid diallyl ester (shown in a formula II); then the malic acid diallyl ester reacts with a peralcohol to obtain the malic acid radical water-borne epoxy resin. The malic acid radical water-borne epoxy resin uses the malic acid which is rich in biological resource as the raw material, is favorable for lowering the amount of oil resources consumed by a high polymer material and lowering the emission of CO2, and opens up a new approach to prepare the water-borne epoxy resin. The malic acid radical water-borne epoxy resin has the characteristic of water-solubility, can be applied in the field where water is used as a resolvent, and has a wide application prospect.

Description

technical field [0001] The invention relates to the field of bio-based polymer materials, in particular to a malic acid-based waterborne epoxy resin and a preparation method thereof. Background technique [0002] With the depletion of petroleum resources, finding sustainable, high-quality and cheap petroleum substitutes is the key to the existence and development of the polymer industry. Bio-based polymer materials use renewable resources as the main raw material. While reducing the consumption of petrochemical products in the plastics industry, it also reduces the environmental pollution during the production of petroleum-based raw materials. It is an important development direction of current polymer materials. Important practical value and broad development space. [0003] Malic acid is one of the intermediates of the tricarboxylic acid cycle, and it exists in various fruits such as apples, grapes, and hawthorns. As its raw material, fumaric acid, can be converted from b...

Claims

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Application Information

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IPC IPC(8): C07D303/16C07D301/12C07D301/14C07D301/19
Inventor 马松琪刘小青朱锦樊利波
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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