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Degradable cyclic acetal and cyclic ketal diamine epoxy resin curing agent and application thereof

An epoxy resin curing and cyclic acetal technology, which is applied in the fields of organic chemistry, fiber chemistry, textiles and papermaking, etc., can solve the problems of difficult recycling of composite materials, environmental pollution, and lack of degradation function.

Active Publication Date: 2013-08-14
ADESSO ADVANCED MATERIALS WUHU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The mixed system of latent curing agent and epoxy resin currently used in composite materials has no degradation function, which makes it difficult to recycle waste composite materials, and simple incineration or landfill treatment will cause huge pollution to the environment

Method used

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  • Degradable cyclic acetal and cyclic ketal diamine epoxy resin curing agent and application thereof
  • Degradable cyclic acetal and cyclic ketal diamine epoxy resin curing agent and application thereof
  • Degradable cyclic acetal and cyclic ketal diamine epoxy resin curing agent and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0142] Embodiment 1: the preparation of curing agent I

[0143]

[0144] Curing agent Ⅰ

[0145] Method 1: 189 grams of N-(2-acetaldehyde)phthalimide, 221 grams of N-(2,3-propanediol)phthalimide, 5 grams of anhydrous p-toluenesulfonic acid, 1 liter of toluene was mixed at room temperature, DEAN-STARK refluxed to separate water, reacted for 20 hours, the reaction was completed, lowered to room temperature, added 2 liters of petroleum ether with a boiling range of 60-90, filtered, and used 1 liter of petroleum ether with a boiling range of 60-90°C Wash the solid with ether, dry the solid to obtain 950 g of crude product, add 3.4 liters of 20% NaOH solution, heat and reflux for 10 hours, cool, add chloroform / isopropanol for extraction, separate layers, dry the organic phase with anhydrous sodium sulfate, and distill under reduced pressure , Obtain 80 grams of curing agent I.

[0146] Method 2: Put 800 grams of toluene and 440 grams of 3-chloroglycerin into the reaction flask...

Embodiment 2

[0150] Embodiment 2: the preparation of curing agent II

[0151]

[0152] Curing agent Ⅱ

[0153] (1) In a 5-liter stirred tank, dissolve 221 grams of sodium hydroxide in 1.5L of ethanol, control the temperature below 40°C, add 700 grams of ethanol (3L) solution of p-nitrophenol dropwise at this temperature, drop During the addition process, a solid was produced. After the dropping, reacted at 40°C for 2 hours, and spin-dried to obtain a solid that was p-nitrophenol sodium salt.

[0154] (2) Put 800 grams of toluene and 480 grams of 3-chloroglycerin into the reaction flask, add 660 grams of m-nitroacetophenone and 1.5 grams of p-toluenesulfonic acid under stirring, the system is heated up slowly, and the Dean-Stark refluxes to separate water. TLC detects the end point of the reaction. After the reaction is over, cool down to below 40°C, add an appropriate amount of sodium carbonate to the reaction bottle to adjust the pH value of the reaction solution system to near neutra...

Embodiment 3

[0159] Embodiment 3: the preparation of curing agent III

[0160]

[0161] Curing agent Ⅲ

[0162] (1) Put 800 grams of toluene and 440 grams of 3-chloroglycerin into the reaction bottle, add 600 grams of p-nitrobenzaldehyde and 3 grams of p-toluenesulfonic acid under stirring, the system is heated up slowly, Dean-Stark reflux water separation, TLC detection At the end of the reaction, after the reaction is over, 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 solution system to be close to neutral, then concentrate the reaction solution under reduced pressure, recover most of the toluene, and heat the residue with water. The precipitated solid was filtered and dried to obtain about 1000 g of solid, which was directly carried out to the next step without purification.

[0163] (2) In a 1-liter three-necked round-bottom flask, put 400 milliliters of N,N-dimethylformamide (DMF) int...

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PUM

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Abstract

The invention provides a degradable cyclic acetal and cyclic ketal diamine epoxy resin curing agent. The curing agent can be polymerized with an epoxy resin so as to generate a degradable cross-linking polymer, wherein the degradable cross-linking polymer can be degraded in a mixing system of acid and solvents under the heating and stirring condition. The invention further provides an enhanced composite material which is prepared from the curing agent, the epoxy resin, auxiliary materials and enhancing materials; and the enhanced composite material can be degraded in the mixing system of acid and solvents under the heating and stirring condition, and can be recycled and reused after being neutralized. The enhanced composite material has excellent mechanical properties, is applicable to application fields of different composite materials, and the degrading and recycling method 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 cyclic acetal, cyclic ketal diamine epoxy resin curing agent, and the polymer and reinforced composite material synthesized by the curing agent and epoxy resin and degradation of said polymers and reinforced composites. Background technique [0002] Epoxy resin is an important thermosetting compound. They are widely used in adhesives, structural materials, painting, ceramic manufacturing, printed circuit boards, microelectronics packaging, aerospace industry, etc. Epoxy resins can undergo curing or hardening crosslinking reactions by one of the three methods described below, and the curing chemical reaction mechanism is explained in detail in the Composite Materials Handbook (published by Chapman & Hall in 1998, edited by S.T.Peter, 3rd Chapter, 48-74 pages), the choice of curing agent structure and curing method has a great influence on the proper...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G59/50C07D317/28C08L63/00C08J11/16C08J11/26C08J11/28
CPCC08G59/5046C07D317/28C08J11/24C08K7/06D01F9/12
Inventor 覃兵李欣梁波
Owner ADESSO ADVANCED MATERIALS WUHU CO LTD
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