Synthesis of n‐alkylated quaternary ammonium chitosan and its long‐term antibacterial finish for rabbit hair fabric

Abstract

In this work, n-alkyl chitosan (N-CTS) was obtained by alkylation modification of chitosan with n-butylaldehyde using Schiff alkali method. The etherifying agent 3-chloro-2-hydroxypropyl triethylammonium chloride (CHPTAC-ethyl) was synthesized from triethylamine and epichlorohydrin. The N-CTS and CHPTAC-ethyl were etherized to finally synthesize n-alkyl quaternary ammonium chitosan (N-CCTS). Scanning electron microscope, X-ray diffractometer, Fourier transform infrared, X-ray photoelectron spectroscopy, and 13 CNMR were used to characterize the surface morphology and chemical structure. Viscosity method and spectrophotometry were used to determine its physical and chemical properties. The etherification reaction mechanism was studied systematically and the influence of reaction conditions on the degree of substitution and solubility of N-CCTS was investigated. The minimum inhibitory concentration (MIC) of N-CCTS against Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) was both 0.15 g/L, which was superior to the MIC value of natural chitosan. N-CCTS was used to finish rabbit hair fabric with citric acid as cross-linking agent and sodium hypophosphite as catalyst. The antibacterial and washing resistance of the product were investigated. After 25 times of washing, the antibacterial rate of N-CCTS against E. coli and S. aureus remained stable at about 90%, and the antibacterial rate was higher than that of N-CTS and natural chitosan, and it was a kind of natural polymer longacting antibacterial finishing agent for rabbit hair fabric.

Green biomanufacturing in recombinant collagen biosynthesis: trends and selection in various expression systems

“…146 Collagen is one of the major substances in edible coating blends, and other antioxidant substances can also be added. 147,148 Turmeric–starch–gelatin, 149 gelatin–chitosan–pectin–rosemary essential oil, 150 chitosan–gelatin–phenolic extracts of grape seed and jabuticaba peel, 151 oregano essential oil ( Origanum vulgare )–gelatin–chia mucilage, 152 and tea polyphenol–gelatin films 153 have achieved certain effects in antibacterial, slow-release and antioxidant areas and so on. In addition, natural sheep casings and artificial films prepared from natural collagen with various crosslinking treatments showed excellent performance.…”

Strategies for the Preparation of Chitosan Derivatives for Antimicrobial, Drug Delivery, and Agricultural Applications: A Review

“…The advantages of do ble-quaternary ammonium salt include making CS more cationic and highly soluble water. While developing the novel derivatives of quaternary ammonium CS, the w ter-soluble (3-Chloro-2-hydroxypropyl) trimethy/triethyl ammonium chloride (CHTA or glycidyl trimethyl ammonium chloride serves as an excellent quaternary ammoniu source, which has been employed in nucleophilic substitution reactions, either C2-N or C6-OH, of CS (Scheme 5) [100][101][102][103][104][105][106][107][108]. In recent years, n-alkyl quaternary ammonium (3i) and 2-hydroxypropyl trimethyl ammonium chloride CS (3j') were synthesiz through the reaction of n-alkyl CS or CS with a quaternary ammonium source, CHTA The n-alkyl CS was initially obtained through the alkylation of CS with n-butylaldehy using the Schiff alkali method, followed by reduction using sodium borohydride [10 The optimal synthesis condition for a higher DS (70-90%) of 3i was optimized in vario temperatures, molar ratios of chemicals, and reaction times.…”

“…While developing the novel derivatives of quaternary ammonium CS, the watersoluble (3-Chloro-2-hydroxypropyl) trimethy/triethyl ammonium chloride (CHTAC) or glycidyl trimethyl ammonium chloride serves as an excellent quaternary ammonium source, which has been employed in nucleophilic substitution reactions, either C2-NH 2 or C6-OH, of CS (Scheme 5) [100][101][102][103][104][105][106][107][108]. In recent years, n-alkyl quaternary ammonium CS (3i) and 2-hydroxypropyl trimethyl ammonium chloride CS (3j') were synthesized through the reaction of n-alkyl CS or CS with a quaternary ammonium source, CHTAC.…”

“…In recent years, n-alkyl quaternary ammonium CS (3i) and 2-hydroxypropyl trimethyl ammonium chloride CS (3j') were synthesized through the reaction of n-alkyl CS or CS with a quaternary ammonium source, CHTAC. The n-alkyl CS was initially obtained through the alkylation of CS with n-butylaldehyde using the Schiff alkali method, followed by reduction using sodium borohydride [100]. The optimal synthesis condition for a higher DS (70-90%) of 3i was optimized in various temperatures, molar ratios of chemicals, and reaction times.…”

“…While the extended n-alkyl chain notably reduces the intermolecular hydrogen bonds in CS, it alone does not lead to complete dissolution in water. However, when combined with quaternary ammonium salt, it significantly enhances water solubility [100]. On the other hand, 3j' was further dialyzed with carboxymethyl insulin [101] and other acetate derivatives against deionized water [102], followed by lyophilization to obtain the desired quaternary ammonium CS derivatives (3j; DS: 17.5-40.9% and 46-81%).…”