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 ap

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

Example Embodiment

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

[0027] In the first step, under the protection of nitrogen, add n-butyl lithium dropwise to the cyanuric chloride solution in tetrahydrofuran, control the reaction temperature to -78°C, stir for 1 hour, 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 was lowered to -78°C, and trimethyl borate was added dropwise to it, stirred for 70 minutes, and then warmed to room temperature and stirred for 8 hours;

[0029] In the third step, a rotary evaporator was used to remove the tetrahydrofuran and unreacted trimethyl borate in the reaction solution of the second step to obtain a solid product. The solid product was dissolved in dichloromethane, and then a saturated aqueous ammonium chloride solution was added for extraction. The organic phase was collected, dried over anhydrous sodium sulfate and fi...

Example Embodiment

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

[0036] In the first step, under nitrogen protection, add n-butyllithium dropwise to the cyanuric chloride solution in tetrahydrofuran, control the reaction temperature to -78°C, stir for 5 hours, 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 was lowered to -78°C, and trimethyl borate was added dropwise thereto, stirred for 45 minutes, and then warmed to room temperature and stirred for 8 hours;

[0038] In the third step, a rotary evaporator was used to remove the tetrahydrofuran and unreacted trimethyl borate in the reaction solution of the second step to obtain a solid product. The solid product was dissolved in dichloromethane, and then a saturated aqueous ammonium chloride solution was added for extraction. The organic phase was collected, dried over anhydrous sodium sulfate and filtered...

Example Embodiment

[0040] Example 3 Preparation of N,N',N"-tris[(4',6'-diboron)-2'-triazinyl]-1,3,5-benzenetriamine (BTAm-3Tz-6B) :

[0041] In the first step, cyanuric chloride was dissolved in tetrahydrofuran, and the tetrahydrofuran solution of 1,3,5-benzenetriamine was added dropwise with stirring, and the stirring was continued for 1 hour after the drop; the solvent was removed to obtain a solid product, which was The solid product is 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"-tris[(4',6'-dichloro)-2'-triazinyl]-1,3,5-benzenetriamine Add n-butyllithium dropwise to the medium, control the reaction temperature to -78°C, and stir for 1 hour; add trimethyl borate dropwise to it, stir for 80 minutes, then warm to room temperature and stir for 12 hours;

[0043] In the third step, a rotary evaporator was used to remove the tetrahydrofuran and un...

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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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