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Calixarene-based hindered phenol antioxidant and preparation method and application thereof

A hindered phenolic and aromatic hydrocarbon-based technology, which is applied in ether preparation, organic chemistry, etc., can solve the problems affecting the anti-oxidation performance of polymer materials, affecting the anti-oxidation ability, and compatibility limitations, so as to improve the thermal-oxidative aging resistance. , Inhibit volatilization and migration, the effect that is not easy to play

Inactive Publication Date: 2017-04-19
SOUTH CHINA UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, there are still deficiencies in the application of calixarene to antioxidants: first, calixarene has certain polarity, and the compatibility with non-polar natural rubber materials is limited, which affects the performance of its antioxidant capacity. The steric hindrance of the phenolic hydroxyl group on the calixarene reported to be used in antioxidants is small, which also affects its further improvement of the antioxidant properties of polymer materials to a certain extent

Method used

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  • Calixarene-based hindered phenol antioxidant and preparation method and application thereof
  • Calixarene-based hindered phenol antioxidant and preparation method and application thereof
  • Calixarene-based hindered phenol antioxidant and preparation method and application thereof

Examples

Experimental program
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Embodiment 1

[0028] (1) Synthesis of calixarene-based hindered phenolic antioxidants:

[0029] 0.5g C‐methyl resorcinol calix[4]arene (synthesized according to literature: Ito H, Nakayama T, SherwoodM, Miller D, Ueda M.Characterization and lithographic application of calix[4]resorcinarene derivatives.Chemistry of Materials, 2008,20(1):341‐356) and 0.5g of iminodiacetic acid were added to 12g of absolute ethanol, until the dissolution of C‐methylresorcinol calix[4]arene was completed, and 0.4g of mass concentration was added 37% formaldehyde solution. Then, under the condition of blowing nitrogen, the temperature was raised to 75° C. for 9 hours. After the reaction solution was cooled to room temperature, suction filtration was performed, and the filter residue was dissolved in 35 g of chloroform, and then insoluble iminodiacetic acid was removed by suction filtration to obtain a colorless filtrate. The filtrate was rotary evaporated, and vacuum-dried at 70° C. for 24 hours to obtain a ca...

Embodiment 2

[0034] The difference between this embodiment and Example 1 is: the mass ratio of C‐methylresorcinol calix[4]arenes and absolute ethanol is changed to 1:15, that is, the consumption of absolute ethanol is changed to 7.5 g; the mass ratio of C‐methylresorcinol calix[4]arenes and 37% formaldehyde solution is changed to 1:0.5, that is, the quality of 37% formaldehyde solution is changed to 0.25g; C‐methylresorcinol The mass ratio of calix[4]arene and iminodiacetic acid is changed to 1:0.5, that is, the quality of iminodiacetic acid is changed to 0.25g; the quality of chloroform is changed to C‐methylresorcinol calix[4] 120 times the mass of the aromatic hydrocarbon, that is, changed to 60g; the reaction temperature was changed to 60°C, and the reaction time was changed to 24 hours. FT-IR and mass spectrometry are basically the same figure 1 , 2 , indicating the successful preparation of calixarene-based hindered phenolic antioxidants.

[0035] The thermo-oxidative aging resist...

Embodiment 3

[0037] The difference between this embodiment and Example 1 is: the mass ratio of C-methylresorcinol calix[4]arene and absolute ethanol is changed to 1:20, that is, the consumption of absolute ethanol is changed to 10g ; The mass ratio of C‐methylresorcinols calix [4]arene and 37% formaldehyde solution is changed to 1:3, that is, the quality of 37% formaldehyde solution is changed to 1.5g; C‐methylresorcinols The mass ratio of calix[4]arene to iminodiacetic acid was changed to 1:1, that is, the mass of iminodiacetic acid was changed to 0.5 g; the reaction temperature was changed to 78°C, and the reaction time was changed to 6 hours. FT-IR and mass spectrometry are basically the same figure 1 , 2 , indicating the successful preparation of calixarene-based hindered phenolic antioxidants.

[0038] The thermo-oxidative aging resistance and extraction resistance of natural rubber vulcanizates are shown in Table 1. It can be seen from Table 1 that the k value of natural rubber vu...

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Abstract

The invention discloses a calixarene-based hindered phenol antioxidant and a preparation method and application thereof. The preparation method includes the steps that C-methyl resorcinol Calix [4] arene and iminodiacetic acid are added in absolute ethyl alcohol, an excessive quantity of formaldehyde solution is added after the C-methyl resorcinol Calix [4] arene is completely dissolved, and then under the condition of nitrogen, the temperature rises to 60-78 DEG C and the mixture reacts for 6-24 hours; and the reaction liquid is cooled to the room temperature and then subjected to suction filtration, filter residues are dissolved in chloroform, suction filtration continues to be conducted so that insoluble imido-acetic acid can be removed, then, obtained colorless filtrate is subjected to rotary evaporation and dried, and the calixarene-based hindered phenol antioxidant is obtained. The antioxidant has 8 hindered phenol hydroxide radicals, the molecular weight is 766, and the antioxidant has a good heat and oxygen aging prevention effect and very good extraction prevention performance and can be widely applied in rubber materials.

Description

technical field [0001] The invention relates to the field of antioxidants, in particular to a calixarene-based hindered phenolic antioxidant, and the invention also relates to a preparation method and application of the calixarene-based hindered phenolic antioxidant. Background technique [0002] As an important additive, antioxidants are currently widely used in polymer materials, especially rubber materials, which can reduce thermal-oxidative aging of polymer materials during storage, processing or use, and prolong their service life. However, due to the low molecular weight of traditional antioxidants, there are disadvantages such as poor thermal stability and solvent extraction resistance, and they are easily lost due to heat volatilization or migration during use, which is not conducive to maintaining long-term antioxidant capacity. [0003] Calixarene is the third-generation supramolecular host compound after crown ether and cyclodextrin, and is usually prepared by con...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/178C07C41/01C08L7/00C08K5/13
CPCC07C41/01C07C43/1785C08K5/13C08L2201/08C08L7/00
Inventor 李红强曾幸荣钟勇赖学军
Owner SOUTH CHINA UNIV OF TECH
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