Star-shaped macromolecular antioxidant containing seven hindered phenolic groups and its preparation method and application
A technology of macromolecular antioxidants and hindered phenols, which is 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, not easy to play, and inhibition of volatilization and migration
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Embodiment 1
[0036] (1) Synthesis of star-shaped macromolecular antioxidants containing seven hindered phenolic groups
[0037] In the first step, 4.14g of 3,5-di-tert-butyl-4-hydroxycinnamic acid (DBHCA), 20mL of chloroform and 8mL of chlorinated Sulfoxide, heated up to 50°C, dripped 0.12g dimethylformamide, reacted for 5 hours, and distilled under reduced pressure to remove chloroform and excess thionyl chloride to obtain DBHCA-Cl;
[0038] In the second step, under the protection of nitrogen, weigh 1.476g per-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 20 mL of tetrahydrofuran was used to dissolve the first step product DBHCA‐Cl, and was added dropwise to the reaction system through a constant pressure funnel within 2.0 hours, and the temperature was raised to 30°C to continue the reaction for 48 hours. Rotary evaporation after the completion of the reaction to obtain a light y...
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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