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Triazine boric acid derivatives and preparation methods thereof

A technology of boric acid derivatives and triazines, which is applied in the field of triazine boric acid derivatives and their preparation, can solve the problems of insufficient environmental protection of organic flame retardants, and achieve the effect of solving high toxicity

Active Publication Date: 2013-10-30
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to solve the defects of insufficient environmental protection of existing organic flame retardants and expand the types and application fields of boric acid derivatives, the present invention provides three triazine boric acid derivatives and their preparation methods

Method used

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  • Triazine boric acid derivatives and preparation methods thereof
  • Triazine boric acid derivatives and preparation methods thereof
  • Triazine boric acid derivatives and preparation methods thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 12

[0026] Example 12, Preparation of 4,6-triboronic acid group-1,3,5-triazine (Tz-3B):

[0027] In the first step, under the protection of nitrogen, add n-butyllithium dropwise to the tetrahydrofuran solution of cyanuric chloride, control the reaction temperature at -78°C, stir for 1 hour, and then raise the temperature to room temperature and stir for 60 minutes;

[0028] In the second step, the temperature of the reaction solution obtained in the first step is lowered to -78°C, and trimethyl borate is added dropwise therein, stirred for 70 minutes, then warmed up to room temperature and stirred for 8 hours;

[0029] In the third step, a rotary evaporator is used to remove tetrahydrofuran and unreacted trimethyl borate in the reaction liquid of the second step to obtain a solid product. Dissolve the solid product with dichloromethane, then add saturated aqueous ammonium chloride for extraction, collect the organic phase, dry with anhydrous sodium sulfate and filter, and remove t...

Embodiment 22

[0035] Example 22, Preparation of 4,6-triboronic acid group-1,3,5-triazine (Tz-3B):

[0036] In the first step, under the protection of nitrogen, add n-butyllithium dropwise to the tetrahydrofuran solution of cyanuric chloride, control the reaction temperature to -78°C, stir for 5 hours, and then raise the temperature to room temperature and stir for 45 minutes;

[0037] In the second step, the temperature of the reaction solution obtained in the first step is lowered to -78°C, and trimethyl borate is added dropwise therein, stirred for 45 minutes, then warmed up to room temperature and stirred for 8 hours;

[0038] In the third step, a rotary evaporator is used to remove tetrahydrofuran and unreacted trimethyl borate in the reaction liquid of the second step to obtain a solid product. Dissolve the solid product with dichloromethane, then add saturated aqueous ammonium chloride for extraction, collect the organic phase, dry with anhydrous sodium sulfate and filter, and remove ...

Embodiment 3

[0040]Example 3N, N', N "-three [(4', 6'-diboronic acid base) -2'-triazinyl] -1,3, the preparation of 5-benzenetriamine (BTAm-3Tz-6B) :

[0041] In the first step, dissolve cyanuric chloride in tetrahydrofuran, add dropwise a solution of 1,3,5-benzenetriamine in tetrahydrofuran under stirring, and continue stirring for 1 hour after dropping; remove the solvent to obtain a solid product, and use ethyl acetate to The solid product was recrystallized to obtain pure N,N',N"-tris[(4',6'-dichloro)-2'-triazinyl]-1,3,5-benzenetriamine;

[0042] The second step is under the protection of nitrogen, to the tetrahydrofuran solution of N, N', N"-three [(4', 6'-dichloro)-2'-triazinyl]-1,3,5-benzenetriamine Add n-butyllithium dropwise to the mixture, control the reaction temperature to -78°C, and stir for 1 hour; add trimethyl borate dropwise therein, stir for 80 minutes, then raise the temperature to room temperature and stir for 12 hours;

[0043] In the third step, a rotary evaporator i...

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Abstract

The invention provides triazine boric acid derivatives and preparation methods thereof. The derivatives are Tz-3B, BTAm-3Tz-6B and BTHo-3Tz-6B. The Tz-3B is obtained by firstly enabling cyanuric chloride to react with n-butyl lithium, then performing nucleophilic substitution reaction with borate ester, and finally performing acid hydrolysis by using dilute hydrochloric acid; the BTAm-3Tz-6B is obtained by enabling the cyanuric chloride to react with 1, 3, 5-benzene triamine, then enabling an obtained product to react with the n-butyl lithium, further performing the nucleophilic substitution reaction with the borate ester, and finally performing acid hydrolysis by using dilute hydrochloric acid; and the BTHo-3Tz-6B is obtained by enabling the cyanuric chloride to react with 1, 3, 5-benzene triol, then enabling the obtained product to react with the n-butyl lithium, further performing the nucleophilic substitution reaction with the borate ester, and finally performing acid hydrolysis by using dilute hydrochloric acid. The obtained products are expected to become excellent environment-friendly organic flame retardants.

Description

technical field [0001] The invention relates to the technical field of flame retardancy of organic polymer synthetic materials, in particular to triazine boric acid derivatives and a preparation method thereof. Background technique [0002] With the development of modern science and technology, polymer materials have played a huge role in the national economy and people's lives. Due to the flammability of polymer materials, fire accidents have increasingly become a social issue of concern to people, so flame retardants continue to develop with the development of polymer materials. As the most active field of flame retardants, organic flame retardants have a wide variety, including halogenated flame retardants, organophosphorus flame retardants, etc., but because of their shortcomings such as large smoke generation, high toxicity, and poor thermal stability , so it is imperative to seek new flame retardants. [0003] In view of the fact that boronic acid derivatives are a c...

Claims

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Application Information

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IPC IPC(8): C07F5/02C08K5/55
Inventor 刘平王美晓彭朝阳
Owner SOUTH CHINA UNIV OF TECH
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