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Cellulose

, Volume 19, Issue 3, pp 925–932 | Cite as

Homogenous synthesis of 3-allyloxy-2-hydroxypropyl-cellulose in NaOH/urea aqueous system

  • Haisong Qi
  • Tim Liebert
  • Thomas Heinze
Original Paper

Abstract

3-Allyloxy-2-hydroxypropylcelluloses (AHP-celluloses), reactive unsaturated cellulose derivatives, were homogeneously synthesized by the reaction of cellulose with allyl glycidyl ether (AGE) in NaOH/urea aqueous solution. Water-soluble AHP-celluloses with DSNMR = 0.32–0.67 were prepared from microcrystalline cellulose. The degree of substitution (DS) of AHP-celluloses could be controlled by varying the molar ratio of AGE and NaOH to AGU and the reaction conditions. The structure of AHP-cellulose samples were characterized by means of FT-IR, NMR spectroscopy and size exclusion chromatography. The cellulose ether shows thermoreversible flocculation. Bromination reactions were carried out as subsequent functionalization both to illustrate the reactivity of the allyl function and to determine the DS values.

Keywords

3-Allyloxy-2-hydroxypropyl celluloses NaOH/urea Synthesis NMR spectroscopy Thermoreversible gelation 

Notes

Acknowledgments

The research leading to these results has received funding from the European Community’s Seventh Framework Programme (FP7/2007–2013) under grant agreement no. 214653 (surface functionalization of cellulose matrices using coatings of functionalized polysaccharides with embedded nano-particles, SurFunCell).

Supplementary material

10570_2012_9687_MOESM1_ESM.doc (220 kb)
Supplementary material 1 (DOC 219 kb)

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Copyright information

© Springer Science+Business Media B.V. 2012

Authors and Affiliations

  1. 1.Institute of Organic Chemistry and Macromolecular Chemistry, Centre of Excellence for Polysaccharide ResearchFriedrich Schiller University of JenaJenaGermany

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