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Degradable hydrazide latent epoxy resin curing agent and application thereof

An epoxy resin curing, latent technology, applied in the preparation of hydrazide, organic chemistry, chemical recycling, etc., can solve the problems of not representing recycling, occupying land, performance degradation, etc.

Active Publication Date: 2014-07-30
芜湖天道绿色新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, the landfill method is to directly bury waste composite materials into the ground, which is simple and easy to implement, and the cost is extremely low, but it occupies land and the source of pollution remains the same.
Although the incineration method can recover part of the energy, the incineration process consumes a lot of energy, and there are still problems from an environmental point of view.
A new technology for recycling carbon fiber composites enables the plastic matrix in the composite to be removed through a special incinerator, and the remaining carbon fibers can be recycled for reuse. Although this method is a step towards sustainable development, it does not represent Fully recyclable, as the plastic matrix is ​​destroyed during the recycling process and cannot be recycled
The fiber material recovered by the pulverization method is reused as an additive, and when added to a certain proportion, the relevant mechanical properties of the material will be reduced
In general, these methods have their limitations to varying degrees, and have disadvantages such as fiber shortening, performance degradation, environmental pollution, and high recycling costs. Therefore, an effective and feasible method for recycling waste composite materials is still an unsolved problem in the field of composite materials.

Method used

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  • Degradable hydrazide latent epoxy resin curing agent and application thereof
  • Degradable hydrazide latent epoxy resin curing agent and application thereof
  • Degradable hydrazide latent epoxy resin curing agent and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0110] Embodiment 1: the preparation of curing agent I

[0111]

[0112] In a 250-ml three-neck round-bottomed flask equipped with a condenser, dissolve 10 g of methylparaben, 6.8 g of dibromomethane, and 3.9 g of sodium hydroxide in 25 ml of N,N-dimethylformamide (DMF ), heated and refluxed for 5 hours, cooled to room temperature, concentrated the mother liquor, added water to precipitate the solid, filtered it with suction, and dried the solid to obtain 3 grams of the intermediate.

[0113] In a 250ml three-necked round-bottomed flask equipped with a condenser, dissolve the intermediate in 10ml of ethanol, add 1.4g of hydrazine hydrate, heat up to 78°C and reflux for 2 hours, cool to below 5°C, solids precipitate out, and filter out The solid was washed with ethanol to obtain 1.5 g of white solid product.

[0114] Melting point: 248-249°C

[0115] 1H-NMR(400MHz,d6-DMSO):9.66(s,2H),7.81(d,4H),7.14(d,4H),5.96(s,2H),4.45(s,4H);

[0116] LC / MS (M+H + ):317.

Embodiment 2

[0117] Embodiment 2: the preparation of curing agent II

[0118]

[0119] In a 250 milliliter three-neck round bottom flask equipped with a condenser, 10 gram of methyl salicylate, 6.8 gram of dibromomethane and 3.9 gram of sodium hydroxide were dissolved in 25 milliliters of DMF, and after reflux for 5 hours, the temperature dropped to At room temperature, the mother liquor was concentrated, and the solid was precipitated by adding water, and the solid was filtered and dried to obtain 3 g of the intermediate.

[0120] In a 250ml three-necked round-bottomed flask equipped with a condenser, dissolve the intermediate in 10ml of ethanol, add 1.4g of hydrazine hydrate, heat up to 78°C and reflux for 2 hours, cool to below 5°C, precipitate a solid, and filter it out The solid was washed with ethanol to obtain 1.1 g of a white solid product.

[0121] Melting point: 174-180°C

[0122] 1H-NMR(400MHz,d6-DMSO):9.32(s,2H),7.59(d,2H),7.46(t,2H),7.39(d,2H),7.12(t,2H),5.95(s, 2H), 4.49(...

Embodiment 3

[0124] Embodiment 3: the preparation of curing agent III

[0125]

[0126] Put 300 grams of toluene, 150 grams of ethyl lactate, 20 grams of paraformaldehyde and 2.2 grams of p-toluenesulfonic acid into a 500 milliliter three-necked round-bottom reaction flask equipped with a water separator, heat up and stir to reflux, and divide the water for 7 hours , the reaction solution was washed 8 times with 100 ml of saturated brine, the organic phase was concentrated, the residue was distilled under reduced pressure, and the fraction before 60° C. was evaporated to obtain 90 g of a residue.

[0127] Dissolve the residue with ethanol, then add 86 g of 85% hydrazine hydrate, heat and reflux for 4 hours, cool, and concentrate the solution under reduced pressure to obtain an oil, freeze, crystallize, filter, wash with ethanol until the filtrate is colorless, and dry to obtain 15 g White solid product.

[0128] Melting point: 138-139°C

[0129] 1H-NMR (400MHz, d6-DMSO): 9.1 (s, 2H), ...

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Abstract

The invention provides a degradable hydrazide latent epoxy resin curing agent. The curing agent can be polymerized with epoxy resin to generate a degradable crosslinked polymer; and the degradable crosslinked polymer can be degraded in a mixed system of an acid and a solvent under the conditions of heating and stirring. The invention also provides a prepreg, consisting of the curing agent, the epoxy resin, an auxiliary material and a reinforcing material. The invention also provides a reinforcing composite material which is prepared from the curing agent, the epoxy resin, the auxiliary material and the reinforcing material. The reinforcing composite material can be prepared by a prepreg forming method. The reinforcing composite material can be degraded in the mixed system of the acid and the solvent under the conditions of heating and stirring, and can be recycled and reused after being neutralized. The reinforcing composite material has excellent mechanical property and is suitable for the field of application of different composite materials; and the degrading and recycling method of the reinforcing composite material is simple, economic, mild in condition and easy to control.

Description

technical field [0001] The present invention relates to epoxy resin curing agent and its application, especially to degradable hydrazide type latent epoxy resin curing agent, as well as the polymer synthesized by the curing agent and epoxy resin, reinforced composite material and the polymer and degradation of reinforced composites. Background technique [0002] Epoxy resins have a large global market as adhesives and coatings, and are one of the industry-standard thermoplastic matrices used to manufacture fiber-reinforced plastics (FRP). FRPs are composite materials composed of a polymer matrix and fibers such as carbon, glass, aramid, natural or other fibers. Fibers help strengthen plastics in terms of strength and elasticity. FRPs are also commonly referred to as "plastic composites," or simply "composites." "Plastic composites" also include non-fibrous materials such as metals or nanomaterials. Plastic composites are widely used in the automotive, aerospace, marine c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G59/40C07C243/38C07C243/28C07C241/04C08G59/20C08J11/16C08J11/26C08J11/28C08L63/00
CPCY02P20/582Y02W30/62
Inventor 李欣覃兵梁波
Owner 芜湖天道绿色新材料有限公司
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