A facile one-pot route to cationic cellulose nanocrystals

Abstract

Pyridinium-grafted-cellulose nanocrystals were prepared by a simple one-pot reaction using 4-(1-bromoethyl/bromomethyl)benzoic acid, pyridine and cellulose nanocrystals (CNCs). The grafting consists of an esterification reaction between 4-(1-bromoethyl/bromomethyl)benzoic acid and CNCs and a nucleophilic attack on the C-Br bond of 4-(1-bromoethyl/bromomethyl)benzoic acid by pyridine. This reaction simplifies existing cationization methods, which leads to a higher grafting density while retaining the CNC crystallinity.

Preparation and characterization of thermally stable cellulose nanocrystals via a sustainable approach of FeCl3-catalyzed formic acid hydrolysis

“…In the present study, a simple cationic modification process was carried out. The cationized CNCs has good application prospect in papermaking, dyeing industries, cosmetics and drug delivery (Jasmani et al 2013).…”

Cationic Poly(2-aminoethylmethacrylate) and Poly(N-(2-aminoethylmethacrylamide) Modified Cellulose Nanocrystals: Synthesis, Characterization, and Cytotoxicity

“…29 The same group recently reported the preparation of cationized pyridinium CNCs with a high degree of substitution via a one-pot esterification/nucleophilic displacement reaction. 30 In this work, our intent was to graft cationic polymers from CNC surfaces by the surface-initiated single-electron-transfer living radical polymerization (SI-SET-LRP) approach using cationic monomers, namely, 2-aminoethyl methacrylate (AEM) hydrochloride and 2-aminoethylmethacrylamide (AEMA) hydrochloride. The choice of these monomers was guided in part by our future interest in developing cationic CNC-based materials for biomedical applications.…”

Synthetic Strategies for the Fabrication of Cationic Surface-Modified Cellulose Nanocrystals

“…Purification of the resulting cationic CNCs was achieved by Soxhlet extraction with dichloromethane and ethanol for 24 h to get rid of any unbound reactants. The success of the surface covalent grafting was confirmed by IR spectroscopy (the presence of the typical carbonyl stretching peak of the ester functionality at ~1720 cm −1 ) and XPS (appearance of In a further attempt to decrease the number of synthetic steps and make the synthetic design more amenable for potential industrial applications, the Thielemans group also developed a simple and heterogeneous one-pot synthetic route for the preparation of cationic pyridinium-grafted CNCs [63]. Unmodified CNCs were treated with 4-(bromomethyl)-or 4-(1-bromoethyl)benzoic acid in the presence of p-toluenesulfonyl chloride and pyridine to append the cationic pyridinium groups on the CNCs' surface (Scheme 8).…”

“…One-pot synthetic route for the design of pyridinium-grafted CNCs. (Adapted from reference [63] with permission from the Royal Society of Chemistry, copyright 2013).…”

“…Furthermore, it was possible to exchange the bromide anion with bistriflimide and the monoanionic orange II dye, thereby allowing the design of a number of ion exchange systems or catalysts using CNCs as a support template. In a further attempt to decrease the number of synthetic steps and make the synthetic design more amenable for potential industrial applications, the Thielemans group also developed a simple and heterogeneous one-pot synthetic route for the preparation of cationic pyridinium-grafted CNCs [63]. Unmodified CNCs were treated with 4-(bromomethyl)-or 4-(1-bromoethyl)benzoic acid in the presence of p-toluenesulfonyl chloride and pyridine to append the cationic pyridinium groups on the CNCs' surface (Scheme 8).…”