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Chitosan-based multifunctional macromolecular rubber anti-aging agent, and preparation method and application thereof

A rubber antioxidant and multi-functional technology, which is applied in the field of rubber additives to achieve the effects of good compatibility, high reactivity and easy access

Active Publication Date: 2021-06-15
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to solve the significant shortcomings of existing rubber antioxidants, the primary purpose of the present invention is to provide a preparation method of chitosan-based multifunctional macromolecular rubber antioxidants

Method used

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  • Chitosan-based multifunctional macromolecular rubber anti-aging agent, and preparation method and application thereof
  • Chitosan-based multifunctional macromolecular rubber anti-aging agent, and preparation method and application thereof
  • Chitosan-based multifunctional macromolecular rubber anti-aging agent, and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Embodiment 1: the synthesis of chitosan-based multifunctional macromolecular rubber antioxidant COS-AO-1

[0048] (1) In a 250mL three-neck flask equipped with mechanical stirring and nitrogen protection, add 3.0g (mole number of chain link 18.0mmol) chitosan (COS) (number average molecular weight is 3000), 2.5g (9.0mmol) carboxyl group-containing Phenolic antioxidant 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid (AO-1) and 100ml dimethyl sulfoxide were stirred for 24 hours, then 1.9g (9.0mmol) of dehydrating agent di Cyclohexylcarbodiimide and 0.11g (0.9mmol) catalyst 4-dimethylaminopyridine were reacted at 20°C for 96h to end the reaction;

[0049] (2) The reaction product obtained in step (1) was purified by post-processing such as filtration and washing, and then vacuum-dried to constant weight at 40°C to obtain chitosan-based multifunctional macromolecular rubber additive COS-AO-1.

[0050] COS-AO-1 was characterized by infrared spectroscopy and hydrogen nuc...

Embodiment 2

[0051] Embodiment 2: the synthesis of chitosan-based multifunctional macromolecular rubber antioxidant COS-AO-2

[0052] (1) In a 250mL three-neck flask equipped with mechanical stirring and nitrogen protection, add 3.0g (mole number of chain links: 18.0mmol) chitosan (COS) (number average molecular weight: 3000), 4.5g (27.0mmol) carboxyl-containing Phenolic antioxidant 3-(3,5-dimethyl-4-hydroxyphenyl) formic acid (AO-2) and 150ml N-methylpyrrolidone were stirred for 12h, then 3.4g (40.5mmol) dehydrating agent N,N '-Diisopropylcarbodiimide and 0.64g (8.1mmol) catalyst pyridine were reacted at 40°C for 48h to end the reaction;

[0053] (2) After the reaction product obtained in step (1) is filtered, washed and purified, it is vacuum-dried to constant weight at 40°C to obtain chitosan-based multifunctional macromolecular rubber additive COS-AO-2.

[0054] COS-AO-2 was characterized by infrared spectroscopy and hydrogen nuclear magnetic resonance spectroscopy. Compared with chi...

Embodiment 3

[0055] Embodiment 3: the synthesis of chitosan-based multifunctional macromolecule rubber antioxidant COS-AO-3

[0056] (1) In a 250mL three-necked flask equipped with mechanical stirring and nitrogen protection, add 3.0g (molar number of chain segments: 18.0mmol) chitosan (COS) (number average molecular weight: 3000), 15.1g (54.0mmol) carboxyl group-containing Phenolic antioxidant 3-(3-methoxy-5-tert-butyl-4-hydroxyphenyl)valeric acid (AO-3) and 100ml N,N-dimethylformamide and 100ml dimethyl sulfoxide After stirring the mixed solvent for 12 hours, add 18.2g (135.0mmol) dehydrating agent 1-hydroxybenzotriazole and 2.73g (27.0mmol) catalyst triethylamine, react at 60°C for 24h, and end the reaction;

[0057] (2) After the reaction product obtained in step (1) was purified by post-processing such as filtration and washing, it was vacuum-dried to constant weight at 40° C. to obtain chitosan-based multifunctional macromolecular rubber additive COS-AO-3.

[0058] COS-AO-3 was char...

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Abstract

The invention discloses a chitosan-based multifunctional macromolecular rubber anti-aging agent, and a preparation method and application thereof. The chitosan-based multifunctional macromolecular rubber anti-aging agent is prepared by carrying out chemical reaction on active amino groups on chitosan and a carboxyl-containing phenolic anti-aging agent in the presence of a solvent, a dehydrating agent and a catalyst. The chitosan-based multifunctional macromolecular rubber anti-aging agent provided by the invention is environment-friendly and not easy to migrate, not only can remarkably improve the thermo-oxidative aging resistance of a rubber material, but also has excellent extraction resistance, can play a lasting thermo-oxidative aging resistance role on the rubber material, can also promote rubber vulcanization and remarkably reduce the positive vulcanization time TC90, and reduces the consumption of a vulcanization accelerator.

Description

technical field [0001] The invention belongs to the technical field of rubber additives, and in particular relates to a chitosan-based multifunctional macromolecular rubber antioxidant and a preparation method and application thereof. Background technique [0002] There are many kinds of rubber additives, including vulcanizing agents, vulcanization accelerators, antioxidants, reinforcing agents, etc. Among them, rubber antioxidants are indispensable rubber additives in the rubber material formulation system, but traditional rubber antioxidants usually have a single function. Moreover, the molecular weight is low, and there are disadvantages such as easy volatilization and migration, poor thermal stability, poor compatibility, and intolerant to solvent extraction. , exposure to solvent extraction and other reasons, resulting in a significant decrease in the performance and service life of the rubber material; at the same time, due to the migration of the rubber antioxidant to...

Claims

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Application Information

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IPC IPC(8): C08B37/08C08L9/06C08L5/08
CPCC08B37/003C08L9/06C08L2201/08C08L5/08
Inventor 刘芳何经纬丁盼
Owner SOUTH CHINA UNIV OF TECH
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