Star macromolecular antioxidant containing seven hindered phenol groups as well as preparation method and application of star macromolecular antioxidant

A technology of macromolecular antioxidants and hindered phenols, applied in the field of antioxidants, can solve the problems of unclear molecular structure and reduction of effective antioxidant components, and achieve the effect of clear molecular structure, difficult to exert, and high proportion

Inactive Publication Date: 2015-11-18
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the introduction of non-effective antioxidant segments, the effective antioxidant components in macromolecular antioxidants are reduced
In addition, most macromolecular antioxidants are prepared by grafting method, and their molecular structure is not clear

Method used

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  • Star macromolecular antioxidant containing seven hindered phenol groups as well as preparation method and application of star macromolecular antioxidant
  • Star macromolecular antioxidant containing seven hindered phenol groups as well as preparation method and application of star macromolecular antioxidant
  • Star macromolecular antioxidant containing seven hindered phenol groups as well as preparation method and application of star macromolecular antioxidant

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] (1) Synthesis of star-shaped macromolecular antioxidants containing seven hindered phenolic groups

[0037] In the first step, add 4.14g of 3,5-di-tert-butyl-4-hydroxycinnamic acid (DBHCA), 20 mL of chloroform and 8 mL of Sulfone, warming up to 50°C, dripping 0.12g dimethylformamide, reacting for 5 hours, distilling under reduced pressure, removing chloroform and excess thionyl chloride, to obtain DBHCA‐Cl;

[0038] In the second step, under the protection of nitrogen, weigh 1.476gper‐2,3‐acetyl‐β‐CD, 0.04g 4‐dimethylaminopyridine (DMAP) and 2g triethylamine and dissolve them in 24mL THF. The system was lowered to 0°C and stirred; then 20mL of tetrahydrofuran was used to dissolve the first step product DBHCA‐Cl, and was added dropwise to the reaction system within 2.0 hours through a constant pressure funnel, and the temperature was raised to 30°C to continue the reaction for 48h. Rotary evaporation after the completion of the reaction to obtain a light yellow solid, w...

Embodiment 2

[0046] The difference between this embodiment and Example 1 is that in the first step, the consumption of thionyl chloride is changed to 12mL, and the consumption of dimethylformamide is changed to 0.16g; the reaction time is changed to 4h; the second step In the process, the amount of 4‐dimethylaminopyridine was changed to 0.08g, the amount of triethylamine was changed to 4g, and the reaction time and temperature were changed to 40°C and 24h, respectively. pass 1 H-NMR and mass spectrometry (basically the same figure 1 , 2 ) and other analyzes proved that the star-shaped macromolecular antioxidant was successfully prepared.

[0047] 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 retention of tensile strength and elongation at break of the natural rubber vulcanizate added with a star-shaped macromolecular antioxidant containing seven hindered phenolic groups after agin...

Embodiment 3

[0049] The difference between this example and Example 1 is that in the first step, the amount of chloroform is changed to 16mL, the amount of thionyl chloride is changed to 6mL, the reaction temperature is changed to 40°C, and the amount of dimethylformamide Change it into 0.08g, change the reaction time into 6h; in the second step, change the consumption of 4-dimethylaminopyridine into 0.06g, change the consumption of triethylamine into 3g, change the dropping time into 3h, change the reaction time into 72h . pass 1 H-NMR and mass spectrometry (basically the same figure 1 , 2 ) and other analyzes proved that the star-shaped macromolecular antioxidant was successfully prepared.

[0050] 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 retention of tensile strength and elongation at break of the natural rubber vulcanizate added with a star-shaped macromolecular antioxid...

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Abstract

The invention discloses a star macromolecular antioxidant containing seven hindered phenol groups as well as a preparation method and application of the star macromolecular antioxidant. The preparation method comprises the following steps: mixing 3,5-di-tert-butyl-4-hydroxycinnamic acid, chloroform and thionyl chloride, heating to 40-60 DEG C, dropping dimethylformamide, reacting for 4-6 h and distilling at reduced pressure so as to obtain DBHCA-Cl; under nitrogen protection, dissolving a polyhydroxyl initiator, 4-dimethylaminopyridine and 2-4 g of triethylamine in tetrahydrofuran, cooling the reaction system to 0-5 DEG C by ice-bath and stirring; dissolving DBHCA-Cl by tetrahydrofuran, dropwise adding dissolved DBHCA-Cl in the reaction system through a constant-pressure funnel within 1.5-3.0 h, heating to 30-40 DEG C and continuously reacting for 24-72 h; collecting and treating so as to obtain the star macromolecular antioxidant containing seven hindered phenol groups. The antioxidant has good thermo-oxidative aging resistance and excellent extraction resistance and can be widely applied to rubber materials.

Description

technical field [0001] The present invention relates to the field of antioxidants, in particular to a star-shaped macromolecular antioxidant containing seven hindered phenolic groups and its preparation method and application. The present invention also relates to a preparation method of the star-shaped macromolecular antioxidant and apply. Background technique [0002] During processing or use, polymer materials, especially rubber materials, are susceptible to aging due to light, heat, oxygen, etc., resulting in a significant decline in their mechanical properties. At present, the most effective way to overcome the aging phenomenon of polymer materials is to add antioxidants. However, the molecular weight of traditional antioxidants is small, generally between 200-600, and they are easy to volatilize or migrate out of the material matrix during long-term use, and have poor solvent extraction resistance, which is likely to cause physical loss and prevent them from fully exe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/16C08L7/00C08L5/16C08K13/02C08K5/09C08K3/22C08K3/26C08K3/06
Inventor 李红强曾幸荣谢湖赖学军吴文剑
Owner SOUTH CHINA UNIV OF TECH
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