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Hindered phenolic antioxidant having stellate molecular structure, and synthesis method and application thereof

A technology of molecular structure and hindered phenols, which is applied in the field of polyamide resin, can solve the problems of high thermal stability and compatibility of antioxidants, and it is difficult for antioxidants to achieve the desired effect, so as to inhibit the yellowing phenomenon , good compatibility and easy access to raw materials

Active Publication Date: 2019-09-24
CATHAY R&D CENT CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

During the high-temperature melt polymerization process of polyamide (temperature reaches 270°C), the thermal stability and compatibility of the antioxidants used are required to be high, and it is difficult for general antioxidants to achieve the desired effect.

Method used

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  • Hindered phenolic antioxidant having stellate molecular structure, and synthesis method and application thereof
  • Hindered phenolic antioxidant having stellate molecular structure, and synthesis method and application thereof
  • Hindered phenolic antioxidant having stellate molecular structure, and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthetic compound MPCP (n=0)

[0031] Add 100G of methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate and 200G of ethylene glycol into the reaction flask. The temperature was raised to 40° C., stirring was started, and 0.45 g of tetraisopropyl titanate was added. The reaction temperature was raised to 75°C and distillate methanol began to collect. The reaction temperature was raised up to 95°C until there was no methanol distillate, and the reaction lasted for 5 hours. After the reaction was stopped, 200 mL of toluene was added to the reaction mixture, and the organic phase was washed three times with 300 mL of saturated brine, and once with 150 mL of pure water. The collected organic phase was concentrated by vacuum distillation to remove all volatile substances to obtain light yellow viscous liquid (ie compound MPCP) 110G.

[0032] Synthesis of Compound I (n=0)

[0033] 150 mL of dichloromethane, 13 G of TEA and 31 G of trimesoyl chloride were added to the rea...

Embodiment 2

[0035] Synthetic compound MPCP(n=1)

[0036] Add 100G of methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate and 265G of diethylene glycol into the reaction flask. The temperature was raised to 40° C., stirring was started, and 0.45 g of tetrabutyl titanate was added. The reaction temperature was raised to 75°C and distillate methanol began to collect. The reaction temperature was raised up to 105°C until there was no methanol distillate, and the reaction lasted for 5 hours. After the reaction was stopped, 200 mL of toluene was added to the reaction mixture, and the organic phase was washed three times with 300 mL of saturated brine, and once with 150 mL of pure water. The collected organic phase was concentrated by vacuum distillation to remove all volatile substances to obtain light yellow viscous liquid (ie compound MPCP) 126G.

[0037] Synthesis of Compound I (n=1)

[0038] 150 mL of dichloromethane, 13 G of TEA and 31 G of trimesoyl chloride were added to the react...

Embodiment 3

[0040] Synthetic compound MPCP(n=2)

[0041] Add 100G of methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate and 450G of triethylene glycol into the reaction flask. The temperature was raised to 40° C., stirring was started, and 0.75 g of tetraisopropyl titanate was added. The reaction temperature was raised to 75°C and distillate methanol began to collect. The reaction temperature was raised up to 110°C until no methanol distillate was present, and the reaction was carried out for a total of 6 hours. After the reaction stopped, 350 mL of toluene was added to the reaction mixture, and the excess triethylene glycol in the lower layer was separated under heating conditions (temperature 50° C.). The organic phase was washed once with 50 mL of pure water, and the collected organic phase was concentrated by vacuum distillation to remove all volatile substances to obtain a light yellow viscous substance (ie compound MPCP) 145G.

[0042] Synthesis of Compound I (n=2)

[0043] 15...

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Abstract

The present invention provides a hindered phenolic compound having a stellate molecular structure, and a preparation method thereof. The hindered phenolic compound of the present invention is a phenolic ester compound, and the synthetic structural unit of the compound is nontoxic, and so the compound can be used as an environmentally friendly antioxidant. The stellate molecular structure is a highly branched molecular structure and has a good dispersing property, so the compound having the structure has a good compatibility with a product when used in the synthesis or modification process of a polymer as a catalyst or an assistant. The stellate molecular structure compound of the present invention achieves remarkable effects when used in the high-temperature melt polymerization of polyamide as the antioxidant.

Description

technical field [0001] The invention relates to the field of polyamide resins, in particular to a hindered phenolic compound used as an antioxidant in the high-temperature melt polymerization process of polyamide. Background technique [0002] During the high-temperature melt polymerization of polyamide, the yellowing phenomenon caused by the degradation of amide bonds often occurs, which is extremely unfavorable for the subsequent processing of polyamide products. Therefore, it is usually necessary to add an appropriate heat stabilizer during the high-temperature melt polymerization of polyamide to prevent the degradation of the polymer chain under high temperature conditions, thereby reducing or eliminating the occurrence of yellowing. [0003] Hindered phenolic antioxidants have the advantages of good antioxidant effect, high thermal stability, low toxicity and low color pollution, and are widely used in the synthesis and modification process of various polymers. Usually...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/14C07C69/767C08G65/337C08G65/332C08L77/06C08K5/134C08L71/02
CPCC07C67/14C07C67/29C07C69/76C08G65/3326C08G65/337C08K5/1345C08L77/06C08L2201/08C08L71/02C07C69/732
Inventor 樊爱龙秦兵兵刘修才
Owner CATHAY R&D CENT CO LTD