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EDC‐Mediated Grafting of Quaternary Ammonium Salts onto Chitosan for Antibacterial and Thermal Properties Improvement
Author(s) -
OyervidesMuñoz Ernesto,
Avérous Luc,
SosaSantillán Gerardo de Jesús,
Pollet Eric,
PérezAguilar Nancy Verónica,
RojasCaldera Claudia Maribel,
FuentesAvilés José Guadalupe,
GarcíaAstrain Clara
Publication year - 2019
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.201800530
Subject(s) - chitosan , chemistry , antibacterial activity , thermogravimetric analysis , ammonium , nuclear chemistry , thermal stability , grafting , antibacterial agent , polymer chemistry , carbodiimide , organic chemistry , bacteria , biochemistry , genetics , antibiotics , biology , polymer
The present study provides antibacterial and thermal improvements of chitosan‐based systems through chemical modification with different quaternary ammonium salts using 1‐ethyl‐3‐(3‐dimethylaminopropyl) carbodiimide (EDC) as mediator. Three different ammonium salts with a carboxylic acid end group are synthesized through a quaternization reaction between bromohexanoic acid and the respective tertiary amines (quinoline, N , N ‐dimethylbenzylamine and pyridine). They are then chemically grafted along the chitosan backbone using EDC as a carboxyl activating agent for the coupling with the primary amine groups. This allows three different chitosan derivatives to be obtained: Quinolinium‐Chitosan (QA‐Cs), Benzalkonium‐Chitosan (BK‐Cs), and Pyridinium‐Chitosan (PA‐Cs), respectively. The chemical structures are characterized by 1 H NMR analysis. The thermal stability is analyzed by thermogravimetric analysis. Antibacterial efficiencies of chitosan derivatives against Pseudomonas aeruginosa and Staphylococcus aureus strains are determined. All the chitosan derivatives show negligible antibacterial activity against Gram‐positive S. aureus strain. However, the antibacterial activity against Gram‐negative P. aeruginosa strain is significantly improved.