Synthesis of N,N-Diethyl, N-Methyl Chitosan Chloride with Certain Quaternization Degree and Molecular Spectroscopic and Thermo-Morphological Study of the Alkylation

Abstract

The quartenizeid chloride derivative of natural polyaminosaccharide chitosan was synthesized in two stages with acetate aldehyde and methyl iodide chemical reaction and ion replacement, which could be soluble in the water and wide pH ranges. The synthesis of the homopolymer was initially carried out with acetate aldehyde in Schiff reaction, and reduction was held on with the presence of NaBH4. The quaternization was accomplished in the acetonitrile medium with methyl iodine by continuous exposure of N2.7-8% quartenized N,N-diethyl, N-methyl chitosan iodine were synthesized with 89-91% yield, obtained by deprotonation of amine groups, with reaction of CH3J and N,N-diethyl chitosan. The ion exchange was carried out at 10% NaCl solution during 24 hours and N,N-diethyl, N-methyl chitosan chloride was obtained. Synthesis was performed with simpler and chemically effective methods compared to previous studies. The structure of product was characterized by FT-IR, UV-Vis, NMR, SEM, TGA, DTA and elemental analysis was determined. Functional changes in the structure of macromolecules were monitored with NMR and UV-Vis, and it was proved that, the main intermediate product was composed to be N,N-diethyl carbocation carrying >C=N-chromophore group. The increasing percent of carbon in content while alkylation is depeering and the presence of halogenated ions (Cl-or J-) after quaternization were observed. It has been determined that, the solubility of N,N-diethyl,N-methyl chitosan chloride or iodide in water and in pH =1-10 increased frequently. Key words. Chitosan; alkylation; diethylmethyl chitosan iodine; quartenization; UV-Vis; NMR

Recent advances of chitosan-based polymers in biomedical applications and environmental protection

“…Chitosan reacts readily with most aliphatic and aromatic aldehydes to produce Schiff bases—imines. The Schiff base formed after the reaction of aldehyde and chitosan could be reduced by sodium borohydride to synthesize N -derivatives of chitosan [ 66 , 67 ]. They could chelate transition metal ions in aqueous solution to form insoluble metal chelates, which could be separated.…”

Immobilization of Levothyroxine in Quaternized N,n-Dietyl N-Methyl Chitosan Hydrogel and Chemical Nature of the Interaction

“…Chitosan average molecular weight 35 kDa (deacetylation degree 85-87%), acetaldehyde (≥99.0%), NaBH 4 (chemically pure ≥96%), acetic acid (Glacial), ethanol (95%), acetone (≥99.9%), diethyl ether (1 ppm inhibitor, anhydrous, ≥99.7%), NaCl (BioXtra, ≥99.5%), Synthesis of N, N-diethyl, N-methyl chitosan chloride (DEMX) was synthesized according to the methodology [23]. The synthesis of DEMX-based hydrogel was performed according to the appropriate methodology.…”

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

“…The diffraction peak of N-CTS at about 10 appears, and the relative intensity of the diffraction peak at about 20 is significantly reduced. After alkylation, the original crystal region ofF I G U R E 2The synthetic route of N-CCTS chitosan is destroyed, and then the macromolecules are reconstituted by hydrogen bond, which changes the original aggregation state and crystal structure of chitosan macromolecules 27. While the diffraction peak of N-CCTS at about 10 almost disappears, the relative strength of the diffraction peak at about 20 further decreases significantly, and the amorphous area increases relatively, indicating that the crystallinity decreases and the product is generated.…”