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Degradable mixed polyamine epoxy resin curing agent, and preparation and composite material recovery thereof

A technology of epoxy resin curing and curing agent, which is applied in the direction of plastic recycling, chemical recycling, recycling technology, etc., and can solve the problems of inability to re-melt, difficult post-processing, and low operating safety

Inactive Publication Date: 2013-04-03
ADESSO ADVANCED MATERIALS WUXI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, the cross-network structure of cured epoxy makes it particularly difficult to remove, recycle and reuse
The cross-linking reactions that typically occur with polyamines compounded with epoxy resins are inherently irreversible, therefore, the material cannot be remelted, reshaped without loss, or easily dissolved
Fiber-reinforced composite materials can be prepared by combining thermosetting epoxy resin matrix with fibers. The cured epoxy resin is difficult to decompose and melt. Correspondingly, fiber-reinforced epoxy resin composite materials are not easy to recycle.
[0006] At present, there are roughly the following recycling processes for fiber-reinforced composite materials: 1. High-temperature thermal degradation (Thermochimica Acta 2007 (454): 109-115), clean fillers and fibers can be recovered, but it needs to be carried out under high temperature conditions , high requirements on equipment; 2. Fluidized bed (Applied surface science 2008(254): 2588-2593) also requires high temperature to recover clean fibers; 3. Supercritical fluid (water (Materials and design 2010(31) : 999-1002), alcohol (Ind.eng.chem.res.2010 (49): 4535-4541), carbon dioxide (CN102181071), etc.) have also achieved the degradation of the redox resin system, but they are all in the laboratory stage , there is still a long distance from real industrialization; 4. Use nitric acid (Journal of applied polymer science, 2004 (95): 1912-1916) to degrade epoxy resin and recover fibers with clean surfaces, but strong acids such as nitric acid Strong corrosiveness, high requirements on equipment, low operation safety, high recycling cost, and difficult post-processing
In general, these methods have their limitations to varying degrees, such as fiber shortening, performance degradation, environmental pollution, and high recycling costs.

Method used

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  • Degradable mixed polyamine epoxy resin curing agent, and preparation and composite material recovery thereof
  • Degradable mixed polyamine epoxy resin curing agent, and preparation and composite material recovery thereof
  • Degradable mixed polyamine epoxy resin curing agent, and preparation and composite material recovery thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0122] Embodiment 1: the synthesis of two (2-chloroethoxy) methane

[0123] 346 grams of toluene and 800 grams of 2-chloroethanol were successively put into the reaction flask, and 164 grams of paraformaldehyde and 4.8 grams of p-toluenesulfonic acid were put into the reaction flask while stirring, the temperature of the system was raised slowly, and the Dean-Stark refluxed to separate the water. When no water droplets were separated, the reaction was extended for another 1 hour, which was the end of the reaction. After the reaction, lower the temperature to below 40°C, add an appropriate amount of sodium carbonate to the reaction bottle, adjust the pH value of the reaction liquid system to be close to neutral, then concentrate the reaction liquid under reduced pressure, recover all the toluene, vacuum distill the residue, and collect 60-75 °C / 200pa, about 753 grams of bis(2-chloroethoxy)methane was obtained, and the yield was 87.6%.

Embodiment 2

[0124] Embodiment 2: the synthesis of two (2-chloroethoxy) methane

[0125] 346 grams of toluene and 800 grams of 2-chloroethanol were successively put into the reaction flask, and 164 grams of paraformaldehyde and 4.8 grams of p-toluenesulfonic acid were put into the reaction flask while stirring, and the temperature of the system was raised slowly, and the Dean-Stark refluxed to separate the water. When no water droplets were separated, the reaction was extended for another 1 hour, which was the end of the reaction. After the reaction, lower the temperature to below 40°C, add an appropriate amount of sodium carbonate to the reaction bottle, adjust the pH value of the reaction liquid system to be close to neutral, then concentrate the reaction liquid under reduced pressure, recover all the toluene, vacuum distill the residue, and collect 60-75 °C / 200pa, about 733 grams of bis(2-chloroethoxy)methane was obtained, and the yield was 85.3%.

Embodiment 3

[0126] Embodiment 3: the synthesis of curing agent 1

[0127] Put 960 grams of concentrated ammonia water and 150 grams of ammonium chloride into the autoclave, stir and dissolve, then add 5 grams of bis(2-chloroethoxy)methane prepared in Example 1 at 150°C, and then heat up to 180°C , stirred and reacted for 2 hours, and TLC detected the end point of the reaction. After the reaction was completed, most of the solution was concentrated under reduced pressure, and the residual solution was transferred to a reaction bottle. 300 ml of mixed solvent of chloroform and ethanol (volume ratio 3:1), extract the aqueous phase 3 times, combine the organic phase, dry the organic phase with anhydrous sodium sulfate, filter, wash the filter cake once with a small amount of solvent, and concentrate the filtrate to Dry to obtain about 3 grams of curing agent I, and its total amine value is 14.9 mmol / g (mmol / g).

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Abstract

The invention provides a novel degradable oligomer (polymer) mixed polyamine epoxy resin curing agent and a synthesis method thereof. The curing agent can react with an epoxy resin system to generate a polymerized substance which can be recovered through degradation; the curing agent, the epoxy resin system, reinforcing materials and auxiliary materials can be prepared into a reinforced composite material; and the material can be recovered through degradation. The synthesis method of the degradable oligomer (polymer) mixed polyamine curing agent provided by the invention is mild in reaction conditions, short in production cycle and suitable for industrial mass production; and the cured substance and the reinforced composite material generated by the reaction of the degradable oligomer (polymer) mixed polyamine curing agent and the epoxy resin can be degraded under normal-pressure mild but specific conditions, the degradation process is simple to operate, and industrial mass recovery can be easily realized.

Description

technical field [0001] The invention relates to the technical field of epoxy resin curing agents, in particular to a novel degradable oligomeric (oligomeric, polymeric) mixed polyamine epoxy resin curing agent and its preparation method, as well as the reinforcement prepared by the curing agent. Composite materials and their degradation and recycling methods. Background technique [0002] Epoxy resin is widely used in the fields of composite materials, castings, electronic appliances, coatings and adhesives due to its excellent physical and mechanical properties, electrical insulation properties, bonding properties with various materials and its flexibility in use and processing , plays an important role in various fields of the national economy. [0003] Epoxy resin curing agent is an additive that chemically reacts with epoxy resin to form a network-like three-dimensional polymer, making the linear resin into a tough solid body. As a thermosetting resin, epoxy resin requ...

Claims

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Application Information

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IPC IPC(8): C08G59/50C08L63/00C08J11/16C08J11/26C08J11/28
CPCY02P20/582Y02W30/62
Inventor 覃兵李欣梁波
Owner ADESSO ADVANCED MATERIALS WUXI CO LTD
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