Abstract <p><b>Objective:</b> The study aims to investigate the solid-state modification of chitosan (Chs) by sorbic acid (SA) through a mechanochemical reaction using a twin-screw extruder under pressure and shear deformation. The goal is to prepare chitosan derivatives with enhanced antifungal properties, particularly against <i>A. niger</i>, to improve their potential applications in food preservation and other industrial fields. <b>Methods:</b> The reaction was carried out in a twin-screw extruder at 80°C, using varying molar ratios of chitosan to sorbic acid (1 : 0.5, 1 : 1, 1 : 1.5). The products were characterized using FT-IR, elemental analysis, thermal analysis (DSC and TGA), dynamic light scattering, and mechanical testing. The antifungal activity of the modified chitosan derivatives was evaluated against <i>A. niger</i>. <b>Results and Discussion:</b> The study found that the degree of substitution (DS) of chitosan derivatives ranged from 0.08 to 0.33, depending on the molar ratio of chitosan to sorbic acid. The FT-IR spectra revealed that the reaction involved both ionic interactions and covalent amide bond formation. The solubility of the derivatives in 2% acetic acid decreased with higher DS values, indicating successful modification. The modified chitosan derivatives exhibited increased antifungal activity against <i>A. niger</i>, with the most effective derivative showing a DS of 0.14. The mechanical properties of films made from the derivatives showed a decrease in elongation at break, suggesting changes in polymer structure due to the acylation process. Thermal stability was also affected, with the insoluble derivatives showing improved thermal stability compared to the unmodified chitosan. <b>Conclusions:</b> The solvent-free mechanochemical acylation of chitosan with sorbic acid in a twin-screw extruder effectively produces chitosan derivatives with enhanced antifungal activity, making them suitable for applications in food preservation and other fields requiring antimicrobial properties. The approach provides a safe, environmentally friendly method for modifying chitosan, expanding its potential uses in various industries such as food, pharmaceuticals, and cosmetics.</p>

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Solid-State Modification of Chitosan by Sorbic Acid

  • М. А. Khavpachev,
  • I. V. Shelomentsev,
  • P. L. Ivanov,
  • Т. А. Akopova,
  • V. V. Potseleev,
  • G. P. Goncharuk,
  • I. O. Kuchkina,
  • M. Z. Bekanova,
  • T. A. Cherdyntseva,
  • A. N. Zelenetskii

摘要

Abstract

Objective: The study aims to investigate the solid-state modification of chitosan (Chs) by sorbic acid (SA) through a mechanochemical reaction using a twin-screw extruder under pressure and shear deformation. The goal is to prepare chitosan derivatives with enhanced antifungal properties, particularly against A. niger, to improve their potential applications in food preservation and other industrial fields. Methods: The reaction was carried out in a twin-screw extruder at 80°C, using varying molar ratios of chitosan to sorbic acid (1 : 0.5, 1 : 1, 1 : 1.5). The products were characterized using FT-IR, elemental analysis, thermal analysis (DSC and TGA), dynamic light scattering, and mechanical testing. The antifungal activity of the modified chitosan derivatives was evaluated against A. niger. Results and Discussion: The study found that the degree of substitution (DS) of chitosan derivatives ranged from 0.08 to 0.33, depending on the molar ratio of chitosan to sorbic acid. The FT-IR spectra revealed that the reaction involved both ionic interactions and covalent amide bond formation. The solubility of the derivatives in 2% acetic acid decreased with higher DS values, indicating successful modification. The modified chitosan derivatives exhibited increased antifungal activity against A. niger, with the most effective derivative showing a DS of 0.14. The mechanical properties of films made from the derivatives showed a decrease in elongation at break, suggesting changes in polymer structure due to the acylation process. Thermal stability was also affected, with the insoluble derivatives showing improved thermal stability compared to the unmodified chitosan. Conclusions: The solvent-free mechanochemical acylation of chitosan with sorbic acid in a twin-screw extruder effectively produces chitosan derivatives with enhanced antifungal activity, making them suitable for applications in food preservation and other fields requiring antimicrobial properties. The approach provides a safe, environmentally friendly method for modifying chitosan, expanding its potential uses in various industries such as food, pharmaceuticals, and cosmetics.