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Polymeric hindered amine light stabilizer HA-88 and preparation method of polymeric hindered amine light stabilizer HA-88 intermediate

A hindered amine light stabilizer, HA-88 technology, applied in the direction of organic chemistry, can solve the problems of adverse effects of HALS light stabilization effect, achieve outstanding application effect, improve molecular weight distribution, and high product quality

Active Publication Date: 2019-03-29
RIANLON +3
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As mentioned above, too high or too low molecular weight will have a bad influence on the light stabilization effect of HALS

Method used

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  • Polymeric hindered amine light stabilizer HA-88 and preparation method of polymeric hindered amine light stabilizer HA-88 intermediate
  • Polymeric hindered amine light stabilizer HA-88 and preparation method of polymeric hindered amine light stabilizer HA-88 intermediate
  • Polymeric hindered amine light stabilizer HA-88 and preparation method of polymeric hindered amine light stabilizer HA-88 intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Disperse 1.84g (10mmol) cyanuric chloride in 20mL toluene, add 4.46g (21mmol) N-butyl-2,2,6,6-tetramethyl-4-piperidinamine dropwise to the system at room temperature After the dropwise addition, add 1.17g of sodium carbonate, heat up to 45°C for reaction, monitor the reaction by HPLC, the content of N-butyl-2,2,6,6-tetramethyl-4-piperidinamine is less than 0.5% The reaction is considered to be complete. After the reaction, the reaction solution was slowly added dropwise to a solution of 0.85 g (4.9 mmol) N,N'-bis(3-aminopropyl)ethylenediamine in 10 mL of toluene. After the dropwise addition, 0.58 g of sodium carbonate was added, and refluxed for dehydration reaction. The reaction was monitored by HPLC, and the reaction was considered as complete when the content of the reaction product in the first step was less than 0.5%. The content of disubstitutes in the intermediate is 87.0%.

[0040] This embodiment also provides a method for preparing HA-88 by using the prepar...

Embodiment 2

[0044] Disperse 1.84g (10mmol) cyanuric chloride in 20mL toluene, add 4.36g (20.5mmol) N-butyl-2,2,6,6-tetramethyl-4-piperidine dropwise to the system at room temperature After completion of the amine, add 2.4mL 30% potassium hydroxide aqueous solution dropwise, heat up to 45°C for reaction, monitor the reaction by HPLC, the content of N-butyl-2,2,6,6-tetramethyl-4-piperidinamine When it is less than 0.5%, the reaction is considered to be over. After the reaction, the reaction solution was slowly added dropwise to a solution of 0.91 g (5.2 mmol) N,N'-bis(3-aminopropyl)ethylenediamine in 10 mL toluene. After completion, 1.2 mL of 30% potassium hydroxide aqueous solution was added dropwise, and refluxed for dehydration reaction. The reaction was monitored by HPLC, and the reaction was considered as complete when the content of the reaction product in the first step was less than 0.5%. The content of disubstitute in the intermediate is 91.1%.

[0045] This embodiment also prov...

Embodiment 3

[0049] Disperse 1.84g (10mmol) of cyanuric chloride in 20mL of xylene, and drop 4.36g (20.5mmol) of N-butyl-2,2,6,6-tetramethyl-4-piperol into the system at room temperature 10mL xylene solution of pyridineamine, after completion, add 2.2mL 30% sodium hydroxide aqueous solution dropwise, heat up to 45°C for reaction, monitor the reaction by HPLC, N-butyl-2,2,6,6-tetramethyl-4 - When the content of piperidinamine is lower than 0.5%, the reaction is considered as complete. After the reaction, the reaction solution was slowly added dropwise to a solution of 0.91 g (5.2 mmol) N,N'-bis(3-aminopropyl)ethylenediamine in 10 mL xylene. After completion, 1.1 mL of 30% sodium hydroxide aqueous solution was added dropwise, and the reaction was refluxed. The reaction was monitored by HPLC, and the reaction was considered as complete when the content of the reaction product in the first step was less than 0.5%. The content of disubstitutes in the intermediate is 82.6%.

[0050] This embo...

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Abstract

The invention relates to a polymeric hindered amine light stabilizer HA-88 and a preparation method of a polymeric hindered amine light stabilizer HA-88 intermediate. The method is characterized in that firstly, N-butyl-2,2,6,6-tetramethyl-4-piperidinamine is reacted with cyanuric chloride; after the reaction is finished, the obtained reaction liquid is dropwise added into an N,N'-bis(3-aminopropyl) ethylenediamine solution; after the dropwise adding is completed, alkali metal hydroxide or salt is added as a catalyst; reaction is performed in a backflow state. The mild reaction conditions areused; by using different feeding methods and sequences, the molecular weight distribution of the intermediate can be obviously improved; the disubstituted substance content of N,N'-bis(3-aminopropyl)ethylenediamine is obviously increased; the condition of mixed ingredients of the product synthesized by the existing process is greatly reduced; the intermediate can be directly applied to HA-88 synthesis without post treatment; the dispersion index of the prepared HA-88 is relatively low; the molecular weight distribution is proper; the product quality is high; the application effect is prominent.

Description

technical field [0001] The invention belongs to the technical field of functional additives for polymer materials, and in particular relates to a preparation method of a polymeric hindered amine light stabilizer HA-88 and an intermediate thereof. Background technique [0002] Hindered Amine Light Stabilizer (HALS for short) is an efficient additive for inhibiting photooxidative degradation of polymer materials, and its light stabilizing effect is 2-4 times that of traditional absorbing light stabilizers. This type of substance has a good synergistic effect with ultraviolet absorbers and antioxidants, and has good compatibility with various polymer materials. Due to its good application performance, HALS has been an important development in the field of polymer anti-aging since its inception, and it is also the fastest-growing class of high-efficiency light stabilizers. [0003] Due to its relatively low molecular weight, the early HALS products have the disadvantages of bei...

Claims

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Application Information

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IPC IPC(8): C07D401/14
CPCC07D401/14
Inventor 王梓范小鹏管波孙春光李海平郭平武
Owner RIANLON
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