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Simple synthesis of mixed cellulose acylate phosphonates applying n-propyl phosphonic acid anhydride

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Abstract

Cellulose mixed esters containing alkylphosphonate and carboxylate groups were prepared homogeneously by a new one-pot method using n-propyl phosphonic acid anhydride (T3P®) in LiCl/N-methyl-2-pyrrolidone (NMP). n-Propyl phosphonic acid anhydride acts as both an activating agent for carboxylic acids and phosphonation reagent. Cellulose mixed esters with DSacyl ranging from 1.4 to 1.8, and DSphos up to 0.7 could be prepared. The structure of the cellulose mixed esters was elucidated by FTIR- and NMR spectroscopy, as well as by GPC and solubility tests.

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References

  • Edgar KJ, Buchanan CM, Debenham JS, Rundquist PA, Seiler BD, Shelton MC, Tindall D (2001) Advances in cellulose ester performance and application. Prog Polym Sci 26:1605–1688

    Article  CAS  Google Scholar 

  • Glasser WG (2004) Prospects for future applications of cellulose acetate. Macromol Symp 208:371–394

    Article  CAS  Google Scholar 

  • Glasser WG, Becker U, Todd JG (2000) Novel cellulose derivatives. Part VI. Preparation and thermal analysis of two novel cellulose esters with fluorine-containing substituents. Carbohydr Polym 42:393–400

    Article  CAS  Google Scholar 

  • Gräbner D, Liebert T, Heinze T (2002) Synthesis of novel adamantoyl cellulose using differently activated carboxylic acid derivatives. Cellulose 9:193–201

    Article  Google Scholar 

  • Granja PL, De Jéso B, Bareille R, Rouais F, Baquey C, Barbosa MA (2006) Cellulose phosphates as biomaterials. In vitro biocompatibility studies. React Funct Polym 66:728–739

    Article  CAS  Google Scholar 

  • Heinze T, Liebert T, Koschella A (2006) Esterification of polysaccharides. Springer, Berlin

    Google Scholar 

  • Holla W, Napierski B, Rebenstock HP (1999) Preparation of imidazole derivatives, useful as intermediates for angiotensin II receptor antagonists, by cyclization of aminoacrylate esters. DE 19802969. CAN 131:131507

    Google Scholar 

  • Hussain MA, Liebert T, Heinze T (2004) Acylation of cellulose with N,N′-carbonyldiimidazole-activated acids in the novel solvent dimethyl sulfoxide/tetrabutylammonium fluoride. Macromol Rapid Commun 25:916–920

    Article  CAS  Google Scholar 

  • Inagaki N, Katsuura K (1980) Reaction of cellulose phosphonate with N-Vinyl-2- pyrrolidone and flame-retardant properties of the product. J Polym Sci Polym Chem Ed 18:441–448

    Article  CAS  Google Scholar 

  • Meudt A, Scherer S, Nerdinger S (2005) Method for producing nitriles and isonitriles by using dehydration reactors with propanephosphonic anhydrides. WO 2005070879. CAN 143:172649

    Google Scholar 

  • Monge S, Cannicioni B, Graillot A, Robin JJ (2011) Phosphorus-containing polymers: a great opportunity for the biomedical field. Biomacromolecules 12:1973–1982

    Article  CAS  Google Scholar 

  • Nagel MCV, Heinze T (2010) Esterification of cellulose with acyl-1H-benzotriazole. Polym Bul 65:873–881

    Article  CAS  Google Scholar 

  • Nehls I, Loth F (1991) 13C-NMR-spektroskopische untersuchungen zur phosphatierung von celluloseprodukten im system H3PO4/harnstoff. Acta Polym 42:233–235

    Article  CAS  Google Scholar 

  • Nuessle AC, Ford FM, Hall WP, Lippert AL (1956) Some aspects of the cellulose-phosphate-urea reaction. Text Res J 26:32–39

    Article  CAS  Google Scholar 

  • Pieschel F, Lange E, Camacho J, Fieseler C, Ikier H (1999) Biosorbents and process for producing the same. WO 9928372. CAN 131:33163

    Google Scholar 

  • Samaranayake G, Glasser WG (1993) Cellulose derivatives with low DS. I. A novel acylation system. Carbohydr Polym 22:1–7

    Article  CAS  Google Scholar 

  • Sealey JE, Frazier CE, Samaranayake G, Glasser WG (2000) Novel cellulose derivatives. V. Synthesis and thermal properties of esters with trifluoroethoxy acetic acid. J Polym Sci Part B Polym Phys 38:486–494

    Article  Google Scholar 

  • Shimizu Y, Hayashi J (1988) A new method for cellulose acetylation with acetic acid. Sen-I Gakkaishi 44:451–456

    Article  CAS  Google Scholar 

  • Tesoro GC, Sello SB, Willard JJ (1968) Flame-retardant properties of phosphonate derivatives of cotton cellulose. Text Res J 38:245–255

    Article  CAS  Google Scholar 

  • Touey GP (1956) Preparation of cellulose phosphates. US 2759924. CAN 51:3440

  • Tsang J, Madden O, Coughlin M, Maiorana A, Watson J, Little NC, Speakman RJ (2009) Degradation of ‘Lumarith’ cellulose acetate. Stud Conserv 54:90–105

    CAS  Google Scholar 

  • Ueda M, Honma T (1988) Synthesis of polyamides by direct polycondensation with propylphosphonic anhydride as an activating agent. Polym J 20:477–483

    Article  CAS  Google Scholar 

  • Vasantha B, Hemantha HP, Sureshbabu VV (2010) 1-Propanephosphonic acid cyclic anhydride (T3P) as an efficient promoter for the lossen rearrangement: application to the synthesis of urea and carbamate derivatives. Synthesis 17:2990–2996

    Google Scholar 

  • Vigo TL, Welch CM (1973) Recent advances in the reaction of cotton. Textilveredlung 8:93–97

    CAS  Google Scholar 

  • Wedel M, Walter A, Montforts FP (2001) Synthesis of metalloporphyrins and metallochlorins for immobilization on electrode surfaces. Eur J Org Chem 2001:1681–1687

    Article  Google Scholar 

  • Wissmann H (1987) Synthesis of peptides and amides with alkylphosphonic-and dialkylphosphinic anhydrides. Phosphorous Sulfur 30:645–648

    Article  CAS  Google Scholar 

  • Wissmann H, Kleiner HJ (1980) New peptide synthesis. Angew Chem Int Ed 19:133–134

    Article  Google Scholar 

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Acknowledgments

The authors thank EC FP project SurFunCell (Surface functionalization of cellulose matrices using coatings of functionalized polysaccharides with embedded nanoparticles), grant agreement Nr. 21653 for financial support. The authors are grateful to Mister J. Brockmann Archimica GmbH (Industriepark Höchst, D-65926 Frankfurt am Main, Germany) for the generous gift of T3P®.

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Authors and Affiliations

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

    Thomas Heinze, Velina Sarbova & Matilde Calado Vieira Nagel

  2. Fibre and Cellulose Technology, Åbo Akademi University, Porthansgatan 3, 20500, Åbo, Finland

    Thomas Heinze

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  1. Thomas Heinze
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  2. Velina Sarbova
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  3. Matilde Calado Vieira Nagel
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Correspondence to Thomas Heinze.

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Thomas Heinze—Member of the European Polysaccharide Network of Excellence (EPNOE). http://www.epnoe.de.eu.

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Heinze, T., Sarbova, V. & Nagel, M.C.V. Simple synthesis of mixed cellulose acylate phosphonates applying n-propyl phosphonic acid anhydride. Cellulose 19, 523–531 (2012). https://doi.org/10.1007/s10570-011-9646-4

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  • DOI: https://doi.org/10.1007/s10570-011-9646-4

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