Health & Environmental Research Online (HERO)


Print Feedback Export to File
1792718 
Journal Article 
Preparation of a C6 quaternary ammonium chitosan derivative through a chitosan schiff base with click chemistry 
Chen, Yu; Wang, F; Yun, D; Guo, Y; Ye, Y; Wang, Y; Tan, H 
2013 
Yes 
Journal of Applied Polymer Science
ISSN: 0021-8995
EISSN: 1097-4628 
129 
6 
3185-3191 
WOS:000320615200013 
In this study, we explored a new method for preparing C6
quaternary ammonium chitosan (CTS) derivatives. The C2NH2 of CTS was first protected by
benzaldehyde. The C6OH of CTS was then transformed into a sulfonyl ester, which was then reacted
with NaN3 through nucleophilic substitution to introduce the N3 group at the CTS C6 position.
This intermediate was reacted in a click chemistry reaction with a terminal alkynyl quaternary
ammonium salt; this was followed by the deprotection of C2NH2 with acid to furnish the C6
quaternary ammonium CTS derivative. The structures and properties of synthesized products in the
reactions were characterized by Fourier transform infrared spectroscopy, NMR, X-ray diffraction,
and thermogravimetric analysis, respectively. The effects of the reaction conditions on the
degree of Schiff-base CTS quaternization were evaluated by elemental analysis. The largest
inhibition zone test and the minimum inhibitory concentration test showed that compared with CTS,
the prepared CTS derivative had significantly improved antibacterial activity toward
Staphylococcus aureus and Escherichia coli. (c) 2013 Wiley Periodicals, Inc. J. Appl. Polym.
Sci., 2013 
functionalization of polymers; modification; polysaccharides