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Synthesis and characterization of aminocellulose sulfates as novel ampholytic polymers

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Abstract

Amino cellulose sulfate (ACS); namely 6-deoxy-6-(ω-aminoethyl) amino cellulose-2,3(6)-O-sulfate (AECS) and 6-deoxy-6-(2-(bis-N′,N′-(2-aminoethyl)aminoethyl)) amino cellulose-2,3(6)-O-sulfate (BAECS) were prepared by a three step synthesis starting with the functionalization of microcrystalline cellulose with p-toluenesulfonyl (tosyl) groups (degree of substitution, DSTos between 0.55 and 1.37). Subsequently the introduction of the sulfate moieties was carried out (DSSulf between 1.09 and 1.27) and the tosyl groups at position 6 were replaced by a nucleophilic substitution reaction. As nucleophilic agents 1,2-diaminoethane and tris-(2-aminoethyl)amine were applied, yielding AECS (DSAEA values between 0.41 and 0.86) and BAECS (DSBAEA values between 0.32 and 0.74), respectively. The ACS samples were characterized by means of elemental analysis, 13C-NMR-, FT-IR-, and UV–Vis spectroscopy. Moreover, the solubility of the samples in water at different pH values and the molecular weights of the samples in aqueous solution were studied.

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Acknowledgments

The research leading to these work received funding from European Community’s Seventh Framework program [FP7/2007-2013] under grant agreement no. 214015. We would like to thank Dr. Wolfgang Guenther (NMR measurements) and Dr. Grit Festag (SEC measurements), Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University Jena for their contributions.

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Authors and Affiliations

  1. Institute of Organic Chemistry and Macromolecular Chemistry, Center of Excellence for Polysaccharide Research, Friedrich Schiller University of Jena, Humboldtstraße 10, 07743, Jena, Germany

    Thomas Heinze, Taha Genco, Katrin Petzold-Welcke & Holger Wondraczek

  2. Laboratory of Fiber and Cellulose Technology, Åbo Akademi University, Porthansgatan 3, 20500, Åbo, Finland

    Thomas Heinze

Authors
  1. Thomas Heinze
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  2. Taha Genco
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  3. Katrin Petzold-Welcke
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  4. Holger Wondraczek
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Correspondence to Thomas Heinze.

Additional information

T. Heinze et al.: Member of the European Polysaccharide Network of Excellence (EPNOE), http://www.epnoe.eu.

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Heinze, T., Genco, T., Petzold-Welcke, K. et al. Synthesis and characterization of aminocellulose sulfates as novel ampholytic polymers. Cellulose 19, 1305–1313 (2012). https://doi.org/10.1007/s10570-012-9725-1

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  • DOI: https://doi.org/10.1007/s10570-012-9725-1

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