Crosslinking reactions of oxidized cellulose fiber. II. Reactions between dialdehyde cellulose and chito‐oligosaccharides on lyocell fabric

Abstract

Antimicrobial nonfibrillated lyocell fibers were developed by crosslinking reactions between dialdehyde cellulose and chito-oligosaccharides. Partially oxidized lyocell fibers with sodium metaperiodate were successfully crosslinked with two water-soluble chito-oligosaccharides with different molecular weights by Schiff base formation and were reduced with sodium borohydride. Infrared spectroscopy measurements showed the characteristic absorption bands caused by the functional groups of each reaction product. The surface chemical compositions of the modified fibers were analyzed with electron spectroscopy. O 1s intensities decreased with the oxidation and crosslinking reaction, whereas N 1s intensities increased with the crosslinking reaction. According to the curve fittings, C 1s spectra were divided into ACH, ACOA/ACNA, AC¼ ¼O, and ACOOA peaks, and their relative peak areas confirmed the reaction results. The degree of fibrillation of the crosslinked fibers decreased with the oxidation levels and chito-oligosaccharide concentrations and increased with the molecular weight of the chito-oligosaccharide. Furthermore, the chito-oligosaccharide-treated lyocell fibers exhibited antimicrobial activity, especially when treated with a chitooligosaccharide of a low weight-average molecular weight.

Antibacterial modification of Lyocell fiber: A review

“…Antibacterial activity of chitosan-coated Lyocell fibers against Escherichia coli and Staphylococcus aureus was confirmed by in vitro experiments. Effectiveness was found to be higher with increasing chitosan molecular weight, in contrast to Han's results (Han and Lee, 2009).…”

“…A disadvantage of periodate oxidation approaches is that they open some of the glucose rings of the polysaccharide main chain, reducing chain rigidity, reducing molecular weight (by oxidation side reactions and by instability of the oxidized products), and by introducing possibly undesired reactivity. Han et al reported crosslinking reactions between dialdehyde cellulose and chitooligosaccharides (Han & Lee, 2009;Han, Lee, & Kim, Fig. 2.…”

“…First, Lyocell fibers were oxidized by potassium periodate to introduce ring-opened 2, 3-dialdehyde monosaccharides. Then the oxidized Lyocell fibers were reacted with chitosan in acetic acid solution to form Schiff's base crosslinks; the method differed from that of Han and Lee (2009) in that there was no reduction step, thus bonds to chitosan were imines (dynamic) rather than amines (stable). This preparation process for chitosan-coated antibacterial Lyocell fibers is illustrated in Fig.…”

Mechanochemical Transformations of Biomass into Functional Materials

“…DAC is amenable to a whole range of reactions from modification with small aliphatic [417] or aromatic [418] amines to reacting with amino-functionalized biopolymers including collagen [419] and chitosan. [420,421] Such reactions are mainly based on Schiff base reactions. [422,423] Cross-linked DAC have been used in a wide range of applications, for example, as an adsorbent of dyes, [424,425] heavy metals [426,427] and DNA, [428] protein immobilization, [429,430] chromatography, [418] nanoparticle carries, and drug delivery.…”

Resource‐Saving Production of Dialdehyde Cellulose: Optimization of the Process at High Pulp Consistency

“…In principle, DAC is amenable to the whole range of reactions and derivatizations known fora ldehydes from organic chemistry textbooks. DAC can be modified with small aromatic [6] or aliphatic amines, [7] and can also react with amino-functionalized biopolymers, such as chitosan [8,9] and collagen. [10] These modifications are mostly based on Schiff base reactions.…”