Skip to main content
Erschienen in: Cellulose 2/2012

01.04.2012

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

verfasst von: Thomas Heinze, Velina Sarbova, Matilde Calado Vieira Nagel

Erschienen in: Cellulose | Ausgabe 2/2012

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

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.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Literatur
Zurück zum Zitat 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 26:1605–1688CrossRef 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 26:1605–1688CrossRef
Zurück zum Zitat Glasser WG (2004) Prospects for future applications of cellulose acetate. Macromol Symp 208:371–394CrossRef Glasser WG (2004) Prospects for future applications of cellulose acetate. Macromol Symp 208:371–394CrossRef
Zurück zum Zitat 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 42:393–400CrossRef 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 42:393–400CrossRef
Zurück zum Zitat Gräbner D, Liebert T, Heinze T (2002) Synthesis of novel adamantoyl cellulose using differently activated carboxylic acid derivatives. Cellulose 9:193–201CrossRef Gräbner D, Liebert T, Heinze T (2002) Synthesis of novel adamantoyl cellulose using differently activated carboxylic acid derivatives. Cellulose 9:193–201CrossRef
Zurück zum Zitat 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 66:728–739CrossRef 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 66:728–739CrossRef
Zurück zum Zitat Heinze T, Liebert T, Koschella A (2006) Esterification of polysaccharides. Springer, Berlin Heinze T, Liebert T, Koschella A (2006) Esterification of polysaccharides. Springer, Berlin
Zurück zum Zitat 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 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
Zurück zum Zitat 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 25:916–920CrossRef 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 25:916–920CrossRef
Zurück zum Zitat 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 18:441–448CrossRef 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 18:441–448CrossRef
Zurück zum Zitat 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 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
Zurück zum Zitat Monge S, Cannicioni B, Graillot A, Robin JJ (2011) Phosphorus-containing polymers: a great opportunity for the biomedical field. Biomacromolecules 12:1973–1982CrossRef Monge S, Cannicioni B, Graillot A, Robin JJ (2011) Phosphorus-containing polymers: a great opportunity for the biomedical field. Biomacromolecules 12:1973–1982CrossRef
Zurück zum Zitat Nagel MCV, Heinze T (2010) Esterification of cellulose with acyl-1H-benzotriazole. Polym Bul 65:873–881CrossRef Nagel MCV, Heinze T (2010) Esterification of cellulose with acyl-1H-benzotriazole. Polym Bul 65:873–881CrossRef
Zurück zum Zitat Nehls I, Loth F (1991) 13C-NMR-spektroskopische untersuchungen zur phosphatierung von celluloseprodukten im system H3PO4/harnstoff. Acta Polym 42:233–235CrossRef Nehls I, Loth F (1991) 13C-NMR-spektroskopische untersuchungen zur phosphatierung von celluloseprodukten im system H3PO4/harnstoff. Acta Polym 42:233–235CrossRef
Zurück zum Zitat Nuessle AC, Ford FM, Hall WP, Lippert AL (1956) Some aspects of the cellulose-phosphate-urea reaction. Text Res J 26:32–39CrossRef Nuessle AC, Ford FM, Hall WP, Lippert AL (1956) Some aspects of the cellulose-phosphate-urea reaction. Text Res J 26:32–39CrossRef
Zurück zum Zitat Pieschel F, Lange E, Camacho J, Fieseler C, Ikier H (1999) Biosorbents and process for producing the same. WO 9928372. CAN 131:33163 Pieschel F, Lange E, Camacho J, Fieseler C, Ikier H (1999) Biosorbents and process for producing the same. WO 9928372. CAN 131:33163
Zurück zum Zitat Samaranayake G, Glasser WG (1993) Cellulose derivatives with low DS. I. A novel acylation system. Carbohydr Polym 22:1–7CrossRef Samaranayake G, Glasser WG (1993) Cellulose derivatives with low DS. I. A novel acylation system. Carbohydr Polym 22:1–7CrossRef
Zurück zum Zitat 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 38:486–494CrossRef 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 38:486–494CrossRef
Zurück zum Zitat Shimizu Y, Hayashi J (1988) A new method for cellulose acetylation with acetic acid. Sen-I Gakkaishi 44:451–456CrossRef Shimizu Y, Hayashi J (1988) A new method for cellulose acetylation with acetic acid. Sen-I Gakkaishi 44:451–456CrossRef
Zurück zum Zitat Tesoro GC, Sello SB, Willard JJ (1968) Flame-retardant properties of phosphonate derivatives of cotton cellulose. Text Res J 38:245–255CrossRef Tesoro GC, Sello SB, Willard JJ (1968) Flame-retardant properties of phosphonate derivatives of cotton cellulose. Text Res J 38:245–255CrossRef
Zurück zum Zitat Touey GP (1956) Preparation of cellulose phosphates. US 2759924. CAN 51:3440 Touey GP (1956) Preparation of cellulose phosphates. US 2759924. CAN 51:3440
Zurück zum Zitat 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 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
Zurück zum Zitat Ueda M, Honma T (1988) Synthesis of polyamides by direct polycondensation with propylphosphonic anhydride as an activating agent. Polym J 20:477–483CrossRef Ueda M, Honma T (1988) Synthesis of polyamides by direct polycondensation with propylphosphonic anhydride as an activating agent. Polym J 20:477–483CrossRef
Zurück zum Zitat 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 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
Zurück zum Zitat Vigo TL, Welch CM (1973) Recent advances in the reaction of cotton. Textilveredlung 8:93–97 Vigo TL, Welch CM (1973) Recent advances in the reaction of cotton. Textilveredlung 8:93–97
Zurück zum Zitat Wedel M, Walter A, Montforts FP (2001) Synthesis of metalloporphyrins and metallochlorins for immobilization on electrode surfaces. Eur J Org Chem 2001:1681–1687CrossRef Wedel M, Walter A, Montforts FP (2001) Synthesis of metalloporphyrins and metallochlorins for immobilization on electrode surfaces. Eur J Org Chem 2001:1681–1687CrossRef
Zurück zum Zitat Wissmann H (1987) Synthesis of peptides and amides with alkylphosphonic-and dialkylphosphinic anhydrides. Phosphorous Sulfur 30:645–648CrossRef Wissmann H (1987) Synthesis of peptides and amides with alkylphosphonic-and dialkylphosphinic anhydrides. Phosphorous Sulfur 30:645–648CrossRef
Zurück zum Zitat Wissmann H, Kleiner HJ (1980) New peptide synthesis. Angew Chem Int Ed 19:133–134CrossRef Wissmann H, Kleiner HJ (1980) New peptide synthesis. Angew Chem Int Ed 19:133–134CrossRef
Metadaten
Titel
Simple synthesis of mixed cellulose acylate phosphonates applying n-propyl phosphonic acid anhydride
verfasst von
Thomas Heinze
Velina Sarbova
Matilde Calado Vieira Nagel
Publikationsdatum
01.04.2012
Verlag
Springer Netherlands
Erschienen in
Cellulose / Ausgabe 2/2012
Print ISSN: 0969-0239
Elektronische ISSN: 1572-882X
DOI
https://doi.org/10.1007/s10570-011-9646-4

Weitere Artikel der Ausgabe 2/2012

Cellulose 2/2012 Zur Ausgabe