Lanthanum sulfonate-calixarene complex antioxidant, and preparation method and application thereof

A technology of lanthanum sulfonate-cup and antioxidant, which is applied in the preparation of sulfonate, organic chemistry, etc., can solve the problems of small steric hindrance of phenolic hydroxyl groups and affect the anti-oxidation performance of polymer materials, and achieve high ratio and excellent anti-oxidation Oxidation ability, effect of inhibiting volatilization and migration

Inactive Publication Date: 2017-03-22
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the steric hindrance of the phenolic hydroxyl group on the calixarene reported to be used as an antioxidant is relatively small, which affects its further improvement of the antioxidant properties of polymer materials to a certain extent.

Method used

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  • Lanthanum sulfonate-calixarene complex antioxidant, and preparation method and application thereof
  • Lanthanum sulfonate-calixarene complex antioxidant, and preparation method and application thereof
  • Lanthanum sulfonate-calixarene complex antioxidant, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] (1) Synthesis of lanthanum sulfonate-calixarene complex antioxidant:

[0032] 1g of 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 1g of anhydrous sodium sulfite were dissolved in 5g of water, 1g of formaldehyde solution with a mass concentration of 37% was added, and reacted at 90°C for 4 hours under nitrogen, then cooled to room temperature, dropwise Add concentrated hydrochloric acid solution to adjust the pH value to 7, add acetone to obtain a precipitate, filter the precipitate and dry it in vacuum at 60°C to constant weight to obtain a sodium sulfonate-calixarene complex intermediate.

[0033] Dissolve 1g of sodium sulfonate-calixarene complex intermediate and 2g of lanthanum chloride hydrate in water, react at 80°C under nitrogen for 8 hours, then cool to room te...

Embodiment 2

[0039] The difference between this embodiment and Example 1 is: the mass ratio of C‐methylresorcinol calix[4]arene and anhydrous sodium sulfate is changed to 1:2, that is, the consumption of anhydrous sodium sulfate is changed The mass ratio of C‐methylresorcinol calix[4]arene and 37% formaldehyde solution is changed to 1:0.5, that is, the quality of 37% formaldehyde solution is changed to 0.5g; C‐methylresorcinol The mass ratio of phenolic calix[4]arene and water is changed to 1:3, that is, the quality of water is changed to 3g; the quality of lanthanum chloride hydrate is changed to 0.5 times of the quality of sodium sulfonate-calixarene complex intermediate, That is, change it to 0.5g; change the reaction temperature in the first step to 80°C, and change the reaction time to 6 hours; change the reaction temperature to 85°C in the second step, and change the reaction time to 4 hours; the first and second steps of vacuum drying The temperature was changed to 50°C. FT-IR and ...

Embodiment 3

[0042] The difference between this embodiment and Example 1 is: the mass ratio of C‐methylresorcinol calix[4]arenes and anhydrous sodium sulfate is changed to 1:0.5, that is, the amount of anhydrous sodium sulfate is changed The mass ratio of C‐methylresorcinol calix[4]arene and 37% formaldehyde solution was changed to 1:2, that is, the quality of 37% formaldehyde solution was changed to 2g; C‐methylresorcinol The mass ratio of phenolic calix[4]arenes and water is changed to 1:5, that is, the quality of water is changed to 5g; That is, change it to 3g; change the reaction temperature in the first step to 95°C, and change the reaction time to 2 hours; change the reaction temperature to 70°C, and change the reaction time to 10 hours in the second step. FT-IR and mass spectrometry are basically the same figure 1 , 2 , indicating the successful preparation of lanthanum sulfonate-calixarene complex antioxidant.

[0043] The thermal and oxidative aging resistance properties of na...

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Abstract

The invention discloses a lanthanum sulfonate-calixarene complex antioxidant, and a preparation method and application thereof. The preparation method comprises the following steps: by using C-methylresorcinol calix[4]arene and a formaldehyde solution as raw material, firstly preparing a sodium sulfonate-calixarene intermediate under the action of anhydrous sodium sulfate, and carrying out reaction on the sodium sulfonate-calixarene intermediate and lanthanum chloride hydrate to obtain the lanthanum sulfonate-calixarene complex antioxidant. The antioxidant has high phenolic hydroxyl proportion; the contained lanthanum element has long atomic radius and abundant empty tracks, thereby being beneficial to removing free radicals generated in the ageing process; and the antioxidant has favorable thermal oxidative aging resistance, and can be widely used in rubber materials.

Description

technical field [0001] The invention relates to an antioxidant, in particular to a lanthanum sulfonate-calixarene complex antioxidant, and also relates to a preparation method and application of the lanthanum sulfonate-calixarene complex antioxidant. Background technique [0002] Antioxidant is an important additive widely used in polymer materials, especially rubber materials, which can reduce the thermo-oxidative aging of these materials during storage, processing or use, and prolong their service life. However, due to the low molecular weight of traditional antioxidants, their thermal stability is poor, 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 condensation reaction of phenols (such as p-tert-butylphenol and resorcinol) and aldehydes. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08K5/42C08K13/02C08K5/09C08K3/22C08K3/26C08K3/06C07C303/32C07C309/24
CPCC08K5/42C07C303/32C08K3/06C08K3/22C08K3/26C08K5/09C08K13/02C08K2003/265C08K2201/011C08L2201/08
Inventor 李红强曾幸荣钟勇赖学军
Owner SOUTH CHINA UNIV OF TECH
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