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Synthetic method of hindered phenol/hindered amine intramolecular compound anti-oxidant

A synthesis method and hindered amine technology, which are applied in the fields of fine chemicals and polymer materials, can solve the problems of few reports on the compounding of hindered phenols and hindered amine light stabilizers, and achieve a product with excellent performance, high yield, and easy operation Effect

Inactive Publication Date: 2012-06-27
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] There are few reports on the combination of hindered phenol and hindered amine light stabilizer

Method used

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  • Synthetic method of hindered phenol/hindered amine intramolecular compound anti-oxidant
  • Synthetic method of hindered phenol/hindered amine intramolecular compound anti-oxidant
  • Synthetic method of hindered phenol/hindered amine intramolecular compound anti-oxidant

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Accurately weigh 5.56g (0.02mol) of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid, put it into a three-necked bottle, add 50mL of chloroform to dissolve, and then place it at a constant temperature of 50°C In a magnetically stirred water bath, slowly add 3.6 mL (0.05 mol) of thionyl chloride dropwise with a constant pressure dropping funnel to carry out a substitution reaction, stop the reaction after 5 hours, and distill under reduced pressure to remove chloroform and unreacted thionyl chloride. Pale yellow crystals of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyl chloride were obtained with a yield of 98.2%.

[0045] Dissolve 5.94g (0.02mol) of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyl chloride in 50mL of acetone and put it into a three-neck flask, cool to 0-5°C in an ice bath, and stir Slowly add 3.95g (0.01mol) of N,N'-bis(2,2,6,6-tetramethyl-4-piperidinyl)-1,6-hexanediamine in acetone solution, after the addition After reacting for 1 h, 4 mL of aqueous...

Embodiment 2

[0051] Accurately weigh 5.56g (0.02mol) of β-(3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid, put it into a three-necked bottle, add 50mL of dichloromethane to dissolve, and then place it at a constant temperature of 50°C In a magnetic stirring water bath, slowly add 2.88mL (0.04mol) thionyl chloride dropwise with a constant pressure dropping funnel to carry out the substitution reaction, stop the reaction after 4.5h, and distill under reduced pressure to remove dichloromethane and unreacted thionyl chloride , to obtain β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyl chloride as pale yellow crystals with a yield of 98.6%.

[0052] Dissolve 5.94g (0.02mol) of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyl chloride in 50mL of toluene and put it into a three-neck flask, cool it down to 0-5°C in an ice bath, and stir Slowly add 3.95g (0.01mol) of N,N'-bis(2,2,6,6-tetramethyl-4-piperidinyl)-1,6-hexanediamine in toluene solution, after the addition React for 2 hours; then slowly ...

Embodiment 3

[0054] Accurately weigh 5.28g (0.02mol) β-(3,5-di-tert-butyl-4-hydroxyphenyl) acetic acid, put it into a three-necked bottle, add 50mL N, N'-dimethylformamide to dissolve, and then Place in a constant temperature magnetically stirred water bath at 60°C, slowly add 2.16mL (0.03mol) thionyl chloride dropwise with a constant pressure dropping funnel to carry out the substitution reaction, stop the reaction after 4h, and distill under reduced pressure to remove N,N'-dichloride Methylformamide and unreacted thionyl chloride gave light yellow crystals of β-(3,5-di-tert-butyl-4-hydroxyphenyl)acetyl chloride with a yield of 96.7%.

[0055] Dissolve 5.64g (0.02mol) of β-(3,5-di-tert-butyl-4-hydroxyphenyl) acetyl chloride in 50mL of acetone and put it into a three-neck flask, cool to 0-5°C in an ice bath, and stir Slowly add 3.95g (0.01mol) of N,N'-bis(2,2,6,6-tetramethyl-4-piperidinyl)-1,6-hexamethylenediamine in acetone solution, after the addition After reacting for 1 h, 4.5 mL of a...

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Abstract

The invention provides a synthetic method of a hindered phenol / hindered amine intramolecular compound anti-oxidant, comprising the following steps of: dissolving a compound I in a solvent A, adding thionyl chloride, performing substitution reaction, carrying out underpressure distillation to remove the solvent A and unreacted thionyl chloride so as to obtain a compound II, respectively dissolvingthe compound II and a compound III by the use of a solvent B, mixing, performing amidation reaction, adding an acid binding agent, continuously reacting, filtering after the reaction, washing, and carrying out vacuum drying to obtain the hindered phenol / hindered amine intramolecular compound anti-oxidant. According to the invention, the reaction raw materials are easily available, the method is simple, and the yield is high. As the product molecule contains hindered phenol antioxidation group and hindered amine light stabilizer function group, oxidation resistance of a polymer is raised.

Description

technical field [0001] The invention relates to the fields of fine chemicals and polymer materials, in particular to a synthesis method of a hindered phenol / hindered amine intramolecular composite antioxidant. Background technique [0002] During the processing, storage or use of polymer materials, oxidation reactions are prone to occur, especially when heated, exposed to light or in the presence of heavy metal ions, the automatic oxidation reaction will be accelerated, which will cause the degradation and crosslinking of polymer molecular chains, making Changes in the appearance, physical properties, and mechanical properties of materials affect their use value. There are many ways to prevent polymer oxidation, and adding antioxidants is the most effective and convenient method. Antioxidants are substances that can slow down the automatic oxidation reaction speed of polymers. There are many kinds of them, and their applications involve almost all polymer products. At pres...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/58C08K5/3435C08L77/00C08L23/06C08L23/12C08L25/06
Inventor 夏雷申屠宝卿翁志学
Owner ZHEJIANG UNIV
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