Hindered amine light stabilizer intermediate and preparation method of hindered amine light stabilizer

A hindered amine light stabilizer and intermediate technology, which is applied in the field of polymer material functional additives, can solve the problems of large amount of formaldehyde-containing wastewater and affect product purity, and achieve reduced post-treatment procedures, short melting range, and simplified reactions Process effect

Active Publication Date: 2021-01-19
RIANLON +1
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  • Application Information

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Problems solved by technology

[0012] The main purpose of the present invention is to provide a hindered amine light stabilizer intermediate and a preparation method of the hindered amine light stabilizer, to solve the problem of using formaldehyde or formic acid to carry out N-methylation when producing hindered amine light stabilizer 119 in the prior art The resulting large amount of formaldehyde-containing wastewater is treated and affects the purity of the product

Method used

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  • Hindered amine light stabilizer intermediate and preparation method of hindered amine light stabilizer
  • Hindered amine light stabilizer intermediate and preparation method of hindered amine light stabilizer
  • Hindered amine light stabilizer intermediate and preparation method of hindered amine light stabilizer

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preparation example Construction

[0031] In order to solve the above problems, the present invention provides a preparation method of a hindered amine light stabilizer intermediate, the hindered amine light stabilizer intermediate 2-chloro-4,6-bis(N-butyl-N-1,2 ,2,6,6-pentamethyl-4-piperidinylamino)-1,3,5-triazine, whose structural formula is The preparation method comprises the following steps: in the presence of hydrogen, 1,2,2,6,6-pentamethyl-4-piperidone and n-butylamine undergo hydrogenation substitution reaction to obtain intermediate 1, intermediate 1 has the following structure:

[0032]

[0033] Substitution of intermediate 1 with cyanuric chloride gave 2-chloro-4,6-di(N-butyl-N-1,2,2,6,6-pentamethyl-4-piperidinyl amino)-1,3,5-triazine.

[0034] Above-mentioned reaction route is as follows:

[0035]

[0036] Different from the need to use formaldehyde or formic acid for N-methylation in the traditional preparation process, the present invention uses 1,2,2,6,6-pentamethyl-4-piperidone as the ...

Embodiment 1

[0055] Put 33.8g (0.2mol) 1,2,2,6,6-pentamethyl-4-piperidone, 14.6g (0.2mol) n-butylamine, 5.0g skeleton nickel catalyst and 200ml toluene into the autoclave , replace the air with nitrogen and hydrogen successively, react at 90°C and 3.0 MPa until the hydrogen pressure no longer decreases, the reaction is completed, and the catalyst is removed by filtration to obtain the reaction solution of intermediate 1;

[0056] Dissolve 18.4g (0.1mol) of cyanuric chloride in 300ml of toluene, cool down in an ice-water bath to below 10°C, add the reaction solution of Intermediate 1 dropwise, after the dropwise addition, stir for 1 hour, then add dropwise 36ml of 20% hydrogen Sodium oxide aqueous solution, wherein the molar ratio of sodium hydroxide to intermediate 1 is 1.1:1, and the molar ratio of cyanuric chloride to intermediate 1 is 1:2; the temperature is raised to 60°C for 8 hours, and the liquid is separated after the reaction, organic The phase was washed with water to obtain 2-ch...

Embodiment 2

[0061] Put 33.8g (0.2mol) 1,2,2,6,6-pentamethyl-4-piperidone, 15.3g (0.21mol) n-butylamine, 6.0g skeleton nickel catalyst and 300ml xylene into the autoclave In the process, the air was replaced with nitrogen and hydrogen successively, and the reaction was carried out at 100°C and 4.0 MPa until the hydrogen pressure no longer decreased. After the reaction was completed, the catalyst was removed by filtration to obtain the reaction solution of intermediate 1;

[0062] Dissolve 18.4g (0.1mol) of cyanuric chloride in 200ml of xylene, cool down in an ice-water bath to below 10°C, add the reaction solution of intermediate 1 dropwise, after the dropwise addition, stir for 1 hour, then add dropwise 20.5ml of 30 % sodium hydroxide aqueous solution, wherein the molar ratio of sodium hydroxide to intermediate 1 is 1.1:1, and the molar ratio of cyanuric chloride to intermediate 1 is 1:2; the temperature is raised to 80°C for 12 hours, and the liquid is separated after the reaction , the ...

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Abstract

The invention provides a hindered amine light stabilizer intermediate and a preparation method of a hindered amine light stabilizer. The hindered amine light stabilizer intermediate is 2-chloro-4,6-di(N-butyl-N-1,2,2,6,6-pentamethyl-4-piperidyl amino)-1,3,5-triazine, and the preparation method comprises the following steps: in the presence of hydrogen, carrying out hydrogenation substitution reaction on 1,2,2,6,6-pentamethyl-4-piperidone and n-butyl amine, carrying out substitution reaction on the obtained intermediate 1 and cyanuric chloride to obtain 2-chloro-4,6-di(N-butyl-N-1,2,2,6,6-pentamethyl-4-piperidyl amino)-1,3,5-triazine. Formaldehyde or formic acid does not need to be adopted in the preparation process, the method has the advantages of being small in environmental pollution and equipment corrosion, and after the method is used for reaction preparation of the hindered amine light stabilizer, the target product is high in purity, good in color and luster and short in meltingrange.

Description

technical field [0001] The invention relates to the technical field of polymer material functional additives, in particular to a hindered amine light stabilizer intermediate and a preparation method of the hindered amine light stabilizer. Background technique [0002] Hindered Amine Light Stabilizer (Hindered Amine Light Stabilizer, referred to as HALS) contains hindered piperidinyl in the molecule, which can capture the free radicals produced by the aging of polymer materials and prevent the aging chain reaction of polymer materials; its photostabilization effect It is several times that of traditional light stabilizers, and has a good synergistic effect with ultraviolet absorbers and antioxidants. It is because of its excellent light stability and compatibility with polymer materials that it has become the most widely used at present. A new type of high-efficiency light stabilizer with the highest market share. [0003] HALS products with low relative molecular weight hav...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14
CPCC07D401/14
Inventor 宋歌张会京范小鹏孙春光李海平
Owner RIANLON
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