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Star-type macromolecular hindered phenol antioxidant and preparation method and application thereof

A technology of hindered phenols and macromolecules, used in the field of antioxidants, can solve the problems of reducing the ability to capture free radicals, unclear molecular structure, low effective antioxidant components, etc., and achieve the performance of inhibiting volatilization and migration, and resisting solvent extraction. Excellent effect with excellent thermal oxidation resistance

Inactive Publication Date: 2015-03-25
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the existing macromolecular hindered phenol antioxidants still have some shortcomings: such as low antioxidant efficiency and unclear molecular structure, etc.
Among them, the anti-oxidation efficiency is not high. On the one hand, due to the introduction of non-anti-oxidation groups, the effective anti-oxidation components are low; on the other hand, because most macromolecular antioxidants are based on unsaturated polyolefins or contain Saturated bonds are easy to cross-link with the polymer main chain during the vulcanization process, so that its mobility in the polymer matrix is ​​limited (Studies on polyisobutylene bound paraphenylene diamine antioxidant in natural rubber. Polymer degradation and stability, 1999,63 (2):225‐230.) thereby reducing its ability to capture free radicals

Method used

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  • Star-type macromolecular hindered phenol antioxidant and preparation method and application thereof
  • Star-type macromolecular hindered phenol antioxidant and preparation method and application thereof
  • Star-type macromolecular hindered phenol antioxidant and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] (1) Synthesis of star-shaped macromolecule hindered phenolic antioxidant: the synthesis method is a two-step method.

[0032] The first step, add 1.222g isophorone diisocyanate (IPDI), 0.0012g dibutyltin dilaurate (DBTDL) and 5.00g chlorobenzene in the there-necked flask that is equipped with magnetic stirring, condenser, burette and nitrogen protection, Adjust the temperature to 30°C; dissolve 1.18g of 3,5-di-tert-butyl-4-hydroxymethylphenol (DBHMP) in 30.00g of chlorobenzene, add it dropwise to the reaction system within 1h, and react at constant temperature for 4h. Intermediates containing primary isocyanates are obtained.

[0033]In the second step, the temperature is raised to 70°C, and 0.0024g dibutyltin dilaurate and 0.861g polyhydroxyl initiator (β-CD-core) (synthesized according to the literature: Gou PF, Zhu WP, Xu N, Shen ZQ.Synthesis and characterization of well‐defined cyclodextrin‐centered seven‐arm star poly(e‐caprolactone)s and amphiphilic star poly(e‐c...

Embodiment 2

[0038] The difference between this embodiment and Example 1 is that in the first step, the mol ratio of isophorone diisocyanate and 3,5-di-tert-butyl-4-hydroxymethylphenol is changed to 1.15:1 , that is, the amount of isophorone diisocyanate is changed to 1.278g; the amount of dibutyltin dilaurate is changed to 0.0019g, the constant temperature reaction temperature is 25°C, and the amount of dibutyltin dilaurate in the second step is changed to 0.0026g . FT‐IR and 1 H‐NMR is basically the same as figure 1 , 2 , indicating the successful preparation of star macromolecule hindered phenolic antioxidants.

[0039] The thermo-oxidative aging resistance and extraction resistance of the vulcanizate are shown in Table 1. It can be seen from Table 1 that the k value of natural rubber vulcanizate is 0.51 after thermal oxygen accelerated aging at 100°C for 48 hours; after soaking in 70°C water for 48 hours, and then 100°C thermal oxygen accelerated aging for 48 hours, the k value dro...

Embodiment 3

[0041] The difference between this embodiment and Example 1 is that in the first step, the mol ratio of isophorone diisocyanate and 3,5-di-tert-butyl-4-hydroxymethylphenol is changed to 1.05:1 , that is, the amount of isophorone diisocyanate was changed to 1.167g; the amount of dibutyltin dilaurate was changed to 0.0006g, and the constant temperature reaction temperature was 35°C. The consumption of the dibutyltin dilaurate in the second step is changed into 0.0022g. FT‐IR and 1 H‐NMR is basically the same as figure 1 , 2 , indicating the successful preparation of star macromolecule hindered phenolic antioxidants.

[0042] The thermo-oxidative aging resistance and extraction resistance of the vulcanizate are shown in Table 1. It can be seen from Table 1 that the k value of natural rubber vulcanizate is 0.48 after thermal oxygen accelerated aging at 100°C for 48 hours; after soaking in 70°C water for 48 hours, and then 100°C thermal oxygen accelerated aging for 48 hours, th...

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Abstract

The invention discloses a star-type macromolecular hindered phenol antioxidant and a preparation method and an application thereof. The preparation method comprises the following steps: under the effect of catalyst dibutyltin dilaurate, carrying out reaction on an alcoholic hydroxyl group of a micromolecular antioxidant 3, 5'-di-tertiary butyl-4-methylol phenol and secondary isocyanato of isophorone diisocyanate at 20-40 DEG C to obtain an intermediate containing isocyanato in primary site; and carrying out reaction on the intermediate and primary hydroxyl in a beta-cyclodextrin derivative at 60-80 DEG C to prepare the star-type macromolecular hindered phenol antioxidant. The beta-cyclodextrin derivative has seven primary hydroxyls and 14 acetyls. The star-type macromolecular hindered phenol antioxidant has excellent thermal oxidative aging resistance and extraction resistance and can be widely applied to rubber materials.

Description

technical field [0001] The invention relates to the field of antioxidants, in particular to a star-shaped macromolecular hindered phenolic antioxidant, and the invention also relates to a preparation method and application of the star-shaped macromolecular hindered phenolic antioxidant. Background technique [0002] Hindered phenol antioxidants are widely used in polymer materials, especially rubber materials, to reduce thermal and oxygen aging of polymer materials during storage, processing or use, and to prolong their service life. However, due to the low molecular weight of traditional hindered phenol antioxidants, there are disadvantages such as poor thermal stability and solvent extraction resistance, and are easily lost due to heat volatilization or migration during use, which is not conducive to maintaining long-term antioxidant capacity. . In addition, when polymer materials are used in food packaging, medical care and other fields, low molecular weight antioxidants...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/16C08L7/00C08L5/16C08J3/24
Inventor 李红强谢湖曾幸荣吴文剑赖学军
Owner SOUTH CHINA UNIV OF TECH
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