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Cyanuric chloride-based quaternary ammonium salt compound and preparation method thereof

A technology of quaternary ammonium salt compound and cyanuric chloride, which is applied in the field of quaternary ammonium salt compound and its preparation, can solve the problem of not being able to graft onto the surface of materials, and achieve high charge density, cheap and easy-to-obtain raw materials, and convenient operation Effect

Active Publication Date: 2014-07-09
SHANGHAI UNIV OF ENG SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The quaternary ammonium salt compounds prepared in the above two patents are optical brighteners, although they also have a high charge density, they generally cannot be used for grafting onto the surface of materials

Method used

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  • Cyanuric chloride-based quaternary ammonium salt compound and preparation method thereof
  • Cyanuric chloride-based quaternary ammonium salt compound and preparation method thereof
  • Cyanuric chloride-based quaternary ammonium salt compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Accurately weigh 5.536g of cyanuric chloride and dissolve it in tetrahydrofuran with a volume of 100ml at a temperature of 0°C, and add 7ml of 3-aminopropyltriethoxysilane with a concentration of 98%, and stir for 3 hours. The chemical reaction formula as follows:

[0021]

[0022] Then the system was heated up to 30° C., stirred for 10 minutes, and then 10 ml of triethylamine with a concentration of 99% was added to react for 12 hours to obtain a light yellow suspension. The chemical reaction formula is as follows:

[0023]

[0024] The above light yellow suspension was centrifuged to obtain a light yellow solid, washed three times with tetrahydrofuran, and finally dried in vacuum at 80°C to obtain a quaternary ammonium compound based on cyanuric chloride,

[0025]

[0026] The product identification results are as follows:

[0027] to CDCl 3 The chemical shift (δ / ppm) of the hydrogen in the target product structure is as follows, 4.1~4.2 (1H, 6, singlet), ...

Embodiment 2

[0030] A kind of preparation method based on the quaternary ammonium salt compound of cyanuric chloride, replaces a chlorine on the cyanuric chloride with 3-aminopropyltriethoxysilane, reduces the activity of cyanuric chloride, and then with triethyl Amine reaction sloughs other two chlorines on cyanuric chloride and forms quaternary ammonium compound; Preparation method comprises the following steps:

[0031] (1) At 0°C, stir and react cyanuric chloride and 3-aminopropyltriethoxysilane in tetrahydrofuran for 5 hours, wherein, 3-aminopropyltriethoxysilane and cyanuric chloride The molar ratio is 0.8:1;

[0032] (2) Warm up the system obtained in step (1) to 25°C, stir for 15 minutes, then add triethylamine, the molar ratio of triethylamine to cyanuric chloride is 2:1, continue stirring for 8 hours to obtain light yellow suspension;

[0033] (3) Centrifuge the suspension obtained in step (2) to obtain a light yellow solid, wash it 3 times with tetrahydrofuran, and finally dry...

Embodiment 3

[0036] A kind of preparation method based on the quaternary ammonium salt compound of cyanuric chloride, replaces a chlorine on the cyanuric chloride with 3-aminopropyltriethoxysilane, reduces the activity of cyanuric chloride, and then with triethyl Amine reaction sloughs other two chlorines on cyanuric chloride and forms quaternary ammonium compound; Preparation method comprises the following steps:

[0037] (1) At 2°C, stir and react cyanuric chloride and 3-aminopropyltriethoxysilane in tetrahydrofuran for 4 hours, wherein the cyanuric chloride and cyanuric chloride The molar ratio is 1:1;

[0038] (2) Warm up the system obtained in step (1) to 35°C, stir for 12 minutes, then add triethylamine, the molar ratio of triethylamine to cyanuric chloride is 2.5:1, continue stirring for 10 hours to obtain light yellow suspension;

[0039] (3) Centrifuge the suspension obtained in step (2) to obtain a light yellow solid, wash it 4 times with tetrahydrofuran, and finally dry it in ...

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Abstract

The invention relates to a cyanuric chloride-based quaternary ammonium salt compound and a preparation method thereof. The preparation method comprises the following steps of 1, stirring cyanuric chloride and 3-aminopropyltriethoxysilane in an organic solvent at a temperature of 0-5 DEG C for a reaction for 3-5h, 2, heating the system obtained by the step 1 to 25-40 DEG C, carrying out stirring for 10-15min, adding triethylamine into the system, and sequentially carrying out stirring reaction for 8-12h to obtain a flavescent suspending liquid, and 3, carrying out centrifugal separation on the flavescent suspending liquid obtained by the step 2 to obtain flavescent solids, carrying out washing 3-5 times by an organic solvent and carrying out vacuum drying at a temperature of 60-90 DEG C to obtain the cyanuric chloride-based quaternary ammonium salt compound. Compared with the common quaternary ammonium salt compound, the cyanuric chloride-based quaternary ammonium salt compound has high charge density and can be stably grafted to the material surface by covalent bond effects. The preparation method does not need other assistants, utilizes cheap and easily available raw materials, has mild reaction conditions and can be operated conveniently.

Description

technical field [0001] The invention relates to a quaternary ammonium salt compound and a preparation method thereof, in particular to a cyanuric chloride-based quaternary ammonium salt compound and a preparation method thereof. Background technique [0002] Cyanuric chloride is an important intermediate in organic synthesis. Among them, the three chlorines on cyanuric chloride are relatively active and are easily replaced to form new compounds. However, through literature research, it is found that the method of dechlorinating cyanuric chloride and generating quaternary ammonium compounds is rarely reported. The main reason is that after the dechlorination of cyanuric chloride to form a quaternary ammonium salt, the quaternary ammonium functional group is unstable due to the accumulation of charges. [0003] Chinese patent CN102863813A announced the synthesis and application of a series of quaternary ammonium salts containing dodecyl / tetradecyl, hexadecyl / octadecyl dimeth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/18
Inventor 饶品华姚伟张文启杜永涛王鸾娇徐美燕李英杰
Owner SHANGHAI UNIV OF ENG SCI
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