Abstract
ABSTRACTLactam groups were introduced onto the backbone of hydroxyethyl cellulose (HEC) to modify properties, such as solubility in organic solvents and solution viscosity and to introduce possible antibacterial activity. Functionalization was achieved using 1‐(hydroxymethyl)‐2‐pyrrolidinone (HMP), and the functionalization reactions were investigated using NMR spectroscopy. The covalent attachment between HEC and HMP was confirmed using 1H‐13C correlated NMR experiments. Degrees of functionalization were calculated using integrated 13C NMR spectra, with values of up to 0.9 being demonstrated on the primary alcohol functionality of HEC. The functionalized HECs showed markedly different properties to unfunctionalized HEC, including the ability to swell considerably in water. Functionalized HEC displayed increased thermal stability and reduced solution viscosity compared with unfunctionalized HEC. Moreover, functionalization altered the bacterial adhesion characteristics compared with unfunctionalized HEC. © 2014 The Authors. Journal of Polymer Science Part A: Polymer Chemistry Published by Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 68–78
Highlights
Cellulose, which is a linear assembly of b-Danhydroglucopyranose units (AGU units), is the most abundant biopolymer on Earth with an estimated 1011 tons produced annually.[1,2,3] AGU units are covalently bonded together via the linkage between the C1 anomeric carbon and the C4 carbon atom providing b-1,4-glycosidic bonds.[4]
The E. coli bacteria used in this study present a predominantly negatively charged, hydrophilic surface composed of lipopolysaccharides and outer membrane proteins, whereas S. aureus, possessing a negatively-charged surface composed of peptidoglycan, techoic acids, and surface proteins, is radically different in character.[38]
The incomplete functionalization of the primary alcohols of hydroxyethyl cellulose (HEC) is consistent with the particular structure of the cellulose, notably the presence of intramolecular and intermolecular hydrogen bonding which blocks the accessibility of the primary alcohols to the functionalizing agent
Summary
Cellulose, which is a linear assembly of b-Danhydroglucopyranose units (AGU units), is the most abundant biopolymer on Earth with an estimated 1011 tons produced annually.[1,2,3] AGU units are covalently bonded together via the linkage between the C1 anomeric carbon and the C4 carbon atom providing b-1,4-glycosidic bonds.[4]. DS represents the average number of modified hydroxyl groups per AGU unit, where DS values can range from 0 to 3.8,9 Hydroxyethyl cellulose (HEC) is a widely used, chemically modified cellulosic material that is produced from the etherification reaction between cellulose and ethylene oxide. HEC-type materials have a wide range of applications as thickeners, cosmetic film formers, and stabilizers and suspending agents in the paint industry.[10,11,12] HEC’s insolubility in organic solvents and the absence of chemically distinct functional groups limit considerably its use in industry
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