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Benzothiadiazole modified imidazole compound as well as preparation method and application thereof

A technology of benzothiadiazoles and benzothiadiazoles, which is applied in the field of benzothiadiazole-modified imidazole compounds and its preparation, can solve the problem of high curing temperature of benzoxazines, which is unfavorable to actual industrial production and affects Material physical properties and other issues, to achieve the effect of easy to obtain raw materials, improve latent properties, and overcome short pot life

Pending Publication Date: 2021-09-24
CHANGCHUN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although this method can optimize the storage time at room temperature, the reaction of imidazole at the curing temperature will also be affected, and the curing time will be prolonged, which does not meet the requirements of rapid curing in industrial production; secondly, there is also the use of microcapsule technology to prepare latent curing agent, patent 201911235546.4 discloses a latent curing agent prepared by the microcapsule method, the microcapsule latent curing agent of the present invention uses the active curing agent as the core material and the thermoplastic high polymer polyethylene glycol as the wall material, wherein the The active curing agent is imidazole or its derivatives, and the wall material is carboxyl-modified PEG-2000
In this method, there are many factors affecting the formation of microcapsules during the preparation process, and the reaction is not easy to control; and after the epoxy resin is cured, the microcapsule wall material remains in the epoxy resin system, which affects the physical properties of the material.
Patent 202010289178.8 discloses a benzoxazine epoxy resin copolymer containing phenolic hydroxyl groups and its preparation method. The phenolic hydroxyl groups of benzoxazine containing phenolic hydroxyl groups are protected by intramolecular hydrogen bonds, which can impart The benzoxazine epoxy blend resin has the characteristics of easy storage and latent curing at room temperature, but the curing temperature of benzoxazine is too high, which is not conducive to the application in actual industrial production

Method used

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  • Benzothiadiazole modified imidazole compound as well as preparation method and application thereof
  • Benzothiadiazole modified imidazole compound as well as preparation method and application thereof
  • Benzothiadiazole modified imidazole compound as well as preparation method and application thereof

Examples

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preparation example Construction

[0038] The invention provides a kind of preparation method of benzothiadiazole modified imidazole compound, comprising:

[0039] Under nitrogen atmosphere, under the effect of catalyst, solvent and acid-binding agent, react the imidazole of formula 2 structure and the 4,7-dibromo-2 of formula 3 structure, 1,3-benzothiadiazole compound, The solvent is preferably selected from one of N,N-dimethylformamide, dimethyl sulfoxide or N,N-dimethylacetamide; the catalyst is preferably cuprous iodide, and the The acid-binding agent is preferably selected from one of anhydrous potassium carbonate, triethylamine, sodium hydroxide or potassium hydroxide, the reaction temperature is preferably 140-155°C, the reaction time is preferably 48-72h, and the reaction ends After that, it is preferably cooled to room temperature, diluted with water, filtered, washed and dried to obtain a crude product, dissolved in a solvent, ultrasonically filtered, the filtrate is rotary evaporated, and dried to ob...

Embodiment 1

[0052] 1. Add 15.03g of 2,1,3-benzothiadiazole, 40.62g of N-bromosuccinimide, and 150ml of concentrated sulfuric acid into a 500ml single-necked flask; after mixing evenly, react the mixed solution in an oil bath at 60°C 3h; after the reaction, cool to room temperature, wash with concentrated sulfuric acid in an ice-water bath, filter and dry to obtain 4,7-dibromo-2,1,3-benzothiadiazole.

[0053] 2. Add 31.38g 4,7-dibromo-2,1,3-benzothiadiazole and excess imidazole to a 500ml three-necked flask to meet the requirements of imidazole and 4,7-dibromo-2,1,3-benzene The molar ratio of thiadiazole is 1:3, 2.474g cuprous iodide, 17.756g anhydrous potassium carbonate, 120ml N,N-dimethylformamide, react at 150℃ for three days under nitrogen atmosphere; after the reaction Cool to room temperature, dilute with water, filter, wash and dry to obtain the crude product, dissolve the crude product in dichloromethane, filter with ultrasonic for 30 minutes, spin the filtrate at 45°C, and dry to...

Embodiment 2

[0059] The preparation method and conditions of this example are the same as in Example 1, the difference is that in application, the benzothiadiazole modified imidazole compound BTD-MZ 2 The mass ratio of epoxy resin and E51 type epoxy resin is 10:100 to obtain a latent epoxy resin one-component curing system. It can be stored for more than 850min at 60°C (such as Figure 4 ), the viscosity remained basically unchanged. According to DSC detection, the exothermic temperature of the initial curing reaction is 145.7°C, the highest peak is at 167.9°C, and the exotherm ends at 190.5°C (such as Figure 5 ).

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Abstract

The invention provides a benzothiadiazole modified imidazole compound as well as a preparation method and application thereof, and belongs to the technical field of epoxy resin curing agents. The structural formula of the compound is as shown in formula 1, in the formula 1, N is nitrogen, and R1, R2, R3 and R4 are respectively and independently selected from hydrogen, alkyl chains or phenyl. The invention provides a preparation method of a benzothiadiazole modified imidazole compound and also provides application of the compound as a latent curing agent in curing epoxy resin. The compound is used as a curing agent, a single-component system formed by the compound and epoxy resin is long in storage period, and the epoxy resin can be rapidly cured under medium and high temperature conditions; moreover, the compound and 4,4'-diaminodiphenylmethane can also be used as a co-curing agent of epoxy resin, so that the reaction temperature is reduced, and the reaction rate is increased.

Description

technical field [0001] The invention belongs to the technical field of epoxy resin curing agents, and in particular relates to a benzothiadiazole-modified imidazole compound and a preparation method and application thereof. Background technique [0002] Epoxy resin is a kind of thermosetting resin, which has excellent mechanical properties, chemical resistance, electrical insulation and bonding properties, and is widely used in coatings, adhesives, electronic packaging materials, composite materials and other fields. Epoxy resins are generally low-molecular compounds at room temperature. When used, a curing agent must be added to cause a cross-linking reaction to form a product with a three-dimensional network structure, which is of value for use. Therefore, the curing agent is indispensable in the application of epoxy resin, and even plays a decisive role to some extent. There are many curing agents for epoxy resins, such as amines, acid anhydrides, mercaptans, phenols, im...

Claims

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Application Information

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IPC IPC(8): C07D417/14C08G59/50
CPCC07D417/14C08G59/5073
Inventor 李明张洁尚垒敖玉辉郭宗伟张辉马金鹏
Owner CHANGCHUN UNIV OF TECH
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