Synthesis and characterization of novel water-soluble 6-deoxy-6-(2-amino-2-(hydroxymethyl)propane-1,3-diol)cellulose derivatives

Amino celluloses are semisynthetic polysaccharide derivatives that are functionalized with amino groups. This class of bio-based polymers has a number of interesting properties for advanced applications such as potential antimicrobial activity and pronounced surface affinity towards various material...

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Bibliographic Details
Main Authors: Annett Pfeifer, Martin Gericke, Thomas Heinze
Format: Article
Language:English
Published: KeAi Communications Co., Ltd. 2020-04-01
Series:Advanced Industrial and Engineering Polymer Research
Online Access:http://www.sciencedirect.com/science/article/pii/S2542504820300129
Description
Summary:Amino celluloses are semisynthetic polysaccharide derivatives that are functionalized with amino groups. This class of bio-based polymers has a number of interesting properties for advanced applications such as potential antimicrobial activity and pronounced surface affinity towards various materials. Herein, the synthesis of a novel type of 6-deoxy-6-amino cellulose derivatives with a polar and highly branched substituent (2-amino-2-(hydroxymethyl)propane-1,3-diol/TRIS) is described for the first time. Fundamental principles for the synthesis by nucleophilic displacement of tosylated intermediates are highlighted, thus, providing access to materials with well-defined molecular structures. TRIS-functionalized cellulose derivatives with degrees of substitution (DS) of up to 0.5 were obtained. The solubility and rheological properties of the products showed a strong dependence on the pH value. Due to the unique structural features of the substituent, TRIS amino cellulose derivatives possess a high application potential. Keywords: Amino celluloses, Water soluble polysaccharide derivatives, 2-Amino-2-(hydroxymethyl)propane-1,3-diol, Nucleophilic displacement, NMR spectroscopy
ISSN:2542-5048