Mild and selective oxidation of cellulose fibers in the presence of N-hydroxyphthalimide.

Abstract:

:The oxidation reaction of regenerated cellulose fibers mediated by N-hydroxyphthalimide (NHPI) and various cocatalysts at room temperature for different time intervals and various amounts of low concentration sodium hypochlorite solution has been investigated to produce oxidized cellulose (OC), a biocompatible and bioresorbable polymer. The results revealed that the nonpersistent phthalimide-N-oxyl (PINO) radical generated in situ from NHPI in both, metallic or metal-free systems, is a powerful agent in this kind of transformation. Moreover, the reaction converts highly selectively C(6) primary hydroxyl groups to carboxylic groups under mild reaction conditions and shorter reaction times than previously reported. The amounts of negatively charged groups in OC were determined by means of potentiometric titration. Further characterization of the products were accomplished by using Fourier transform infrared spectroscopy/attenuated total internal reflection spectroscopy (FT-IR/ATR), environmental scanning electron microscopy (ESEM), and X-ray and energy-dispersive X-ray (EDX) spectroscopy. Notably, water retention values of the oxidized fibers increased by 30% in comparison with the original nonoxidized sample, as a result of the introduction of hydrophilic carboxylate groups.

journal_name

Biomacromolecules

journal_title

Biomacromolecules

authors

Coseri S,Nistor G,Fras L,Strnad S,Harabagiu V,Simionescu BC

doi

10.1021/bm9004854

subject

Has Abstract

pub_date

2009-08-10 00:00:00

pages

2294-9

issue

8

eissn

1525-7797

issn

1526-4602

journal_volume

10

pub_type

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