Hindered phenol antioxidant and preparation method thereof

A technology of hindered phenols and antioxidants, applied in the field of hindered phenols antioxidants and its preparation, can solve the problems of polymer antioxidants, the inability to use antioxidant substances, and the impact of antioxidant effects, etc., to achieve improved Heat stability and anti-oxidation performance, improvement of heat resistance stability, effect of enhancing anti-oxidation effect

Active Publication Date: 2020-03-06
SHANDONG LINYI SUNNY WEALTH CHEM CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, it is very difficult to develop new antioxidants for polymers. Not all substances can be used as long as they have antioxidant properties. There is a specific match between polymer materials and antioxidants. Not all substances with antioxidant properties are equal. It can be used as an antioxidant for polymer materials. Due to various complex factors such as molecular weight, melting point, compatibility with polymers, and dispersibility, antioxidant substances may not be used in polymer materials.
Moreover, even if antioxidant substances can be used in polymer materials, problems such as migration, volatilization and extraction of antioxidants in polymer materials need to be considered. If better resistance to migration, volatilization and extraction cannot be achieved , the antioxidant effect of antioxidants cannot be fully exerted, affecting the antioxidant effect
Therefore, it is very difficult to develop antioxidants that can be used in polymers and to fully exert the antioxidant effect.
On this basis, it is more difficult to overcome the defects of existing antioxidants, improve heat resistance stability, and further improve antioxidant performance

Method used

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  • Hindered phenol antioxidant and preparation method thereof
  • Hindered phenol antioxidant and preparation method thereof
  • Hindered phenol antioxidant and preparation method thereof

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preparation example Construction

[0036] The present invention also provides a method for preparing the hindered phenolic antioxidant described in the above technical scheme, including the following steps:

[0037] Under the action of a catalyst, β-(3,5-di-tert-butyl-4-hydroxyphenyl) methyl acrylate is esterified with xylitol to form the hindered phenolic antioxidant represented by formula (1) .

[0038] The reaction route is as follows:

[0039]

[0040] In the present invention, the source of the methyl β-(3,5-di-tert-butyl-4-hydroxyphenyl)acrylate is not particularly limited, and is generally commercially available or prepared according to a preparation method well known to those skilled in the art That's it.

[0041] In the present invention, a specific xylitol is used to react with β-(3,5-di-tert-butyl-4-hydroxyphenyl) methyl acrylate to prepare an antioxidant. Compared with other alcohols, xylitol is used with the above The product made by acrylate can have more suitable molecular weight, melting point, good c...

Embodiment 1

[0058] 1.1 Preparation

[0059] Add 84.8g (0.29mol) of β-(3,5-di-tert-butyl-4-hydroxyphenyl)methyl acrylate into a 250mL four-necked flask equipped with an electric stirrer, thermometer, condenser and methanol receiver. , Xylitol 7.6g (0.05mol), catalyst sodium methoxide 0.10g, heating and stirring, control the temperature at 180±5℃, first react at normal pressure for 6h, then react under reduced pressure for 2h, extract the methanol gas generated by the reaction, and react to No more methanol is formed. The temperature is lowered, the product is recrystallized with isopropanol, filtered, washed with isopropanol, and dried to obtain the product, which has a white solid appearance.

[0060] 1.2 Characterization and testing

[0061] (1) Perform FTIR test and 1H-NMR test on the obtained product, the results are as follows: figure 1 with figure 2 As shown, figure 1 Is the FTIR spectrum of the product obtained in Example 1 of the present invention, figure 2 This is the 1H-NMR spectrum...

Embodiment 2

[0065] Add 84.8g (0.29mol) of β-(3,5-di-tert-butyl-4-hydroxyphenyl)methyl acrylate into a 250mL four-necked flask equipped with an electric stirrer, thermometer, condenser and methanol receiver. , Xylitol 7.6g (0.05mol), catalyst sodium methoxide 0.20g, heating and stirring, control the temperature at 190±5℃, first react at normal pressure for 6h, then react under reduced pressure for 2h, extract the methanol gas generated by the reaction, and react to No more methanol is formed. The temperature is lowered, the product is recrystallized with isopropanol, filtered, washed with isopropanol, and dried to obtain the product, which has a white solid appearance.

[0066] The product was tested according to the characterization and testing of Example 1, and the result showed that the product obtained had the structure of formula (1). The product yield was 92%, and the purity was 98.6%. The melting point of the product is 75.2~76.6℃.

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Abstract

The invention provides a hindered phenol antioxidant and a preparation method thereof. The antioxidant provided by the invention has proper molecular weight and melting point, and good compatibility and combinability with polymers, can be uniformly dispersed in a high polymer material matrix, and can be used as an antioxidant of polymer materials; meanwhile, the antioxidant also has the advantagesof good extraction resistance, volatilization resistance, migration resistance and the like, and can give full play to the antioxidant effect when applied to polymer materials, thus enhancing the antioxidant effect. Moreover, compared with an antioxidant 1010, the antioxidant provided by the invention can improve the heat-resistant stability. In addition, the antioxidant provided by the inventionhas the characteristics of low raw material cost and high reaction yield, and can realize industrial production.

Description

Technical field [0001] The invention relates to an antioxidant for polymer materials, in particular to a hindered phenol antioxidant and a preparation method thereof. Background technique [0002] During the process of polymerization, granulation, storage, processing, and long-term use, polymers are susceptible to light and heat, and are oxidized by oxygen in the air. The mechanical properties of the polymer are lost, and changes such as discoloration, cracking, and loss of gloss occur. Therefore, it is necessary to add antioxidants to improve the processing stability and long-term stability of the polymer. [0003] The types of antioxidants are: hindered phenol antioxidants, phosphite antioxidants, thioester antioxidants, etc. Among them, hindered phenolic antioxidants are one of the most widely used and effective antioxidants. They are widely used because of their advantages of giving protons to terminate the auto-oxidation chain reaction of free radicals, and good synergy with ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/03C07C69/732C08K5/134C08L23/12
CPCC07C67/03C07C69/732C08K5/1345C08L23/12C08L2201/08Y02P20/52
Inventor 李中映付建英刘明月张永兴
Owner SHANDONG LINYI SUNNY WEALTH CHEM CO LTD
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