Formation of N-acylureas on the surface of TEMPO-oxidized cellulose nanofibril with carbodiimide in DMF

Cellulose

Volumn 18, Issue 5, 2011, Pages 1191-1199

  Fujisawa, Shuji ^a   Okita, Yusuke ^a   Saito, Tsuguyuki ^a   Togawa, Eiji ^b   Isogai, Akira ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b FORESTRY AND FOREST PRODUCTS RESEARCH INSTITUTE   (Japan)

Author keywords

Carbodiimide; N acylurea; Nano dispersion; Nanofibril; TEMPO

Indexed keywords

CARBODIIMIDES; N-ACYLUREA; NANO-DISPERSIONS; NANOFIBRIL; TEMPO;

CELLULOSE; CONTACT ANGLE; CRYSTAL STRUCTURE; DIMETHYLFORMAMIDE; ETHERS; KRAFT PROCESS; KRAFT PULP; ORGANIC SOLVENTS; X RAY DIFFRACTION; X RAY DIFFRACTION ANALYSIS;

WOOD;

CARBOXYL GROUPS; CELLULOSE; CONTACT ANGLE; CRYSTAL STRUCTURE; ETHERS; KRAFT PULPS; SOLVENTS; WOOD; X RAY DIFFRACTION;

EID: 79961207948     PISSN: 09690239     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10570-011-9578-z     Document Type: Article

References (27)

1. Angelova P, Kostova K, Tsankov D (2005) A convenient synthesis of long-chain 4-substituted benzyloxycarbonyl alkanethiols for the formation of self assembled monolayers on metal substrates. Cent Eur J Chem 3: 658-667.
2. Azzam F, Heux L, Putaux JL, Jean B (2010) Preparation by grafting onto, characterization, and properties of thermally responsive polymer-decorated cellulose nanocrystals. Biomacromolecules 11: 3652-3659.
3. Berlioz S, Boisseau SM, Nishiyama Y, Heux L (2009) Gas-phase surface esterification of cellulose microfibrils and whiskers. Biomacromolecules 10: 2144-2151.
4. Buchanan GW, Rastegar MF, Enright G (2007) Reaction of RF-palmitic acid-F13 with dicyclohexylcarbodiimide. J Fluor Chem 128: 1026-1028.
5. Chazeau L, Cavaille JY, Canova G, Dendievel R, Boutherin B (1999) Viscoelastic properties of plasticized PVC reinforced with cellulose whiskers. J Appl Polym Sci 71: 1797-1808.
6. Costanzo PJ, Beyer FL (2007) Thermoresponsive, optically active films based on Diels-Alder chemistry. Chem Matter 19: 6168-6173.
7. DeTer DF, Silverstein R (1965) Reactions of carbodiimides. I. The mechanisms of the reactions of acetic acid with dicyclohexylcarbodiimide. J Am Chem Soc 88: 1013-1019.
8. Fujisawa S, Okita Y, Fukuzumi H, Saito T, Isogai A (2011) Preparation and characterization of TEMPO-oxidized cellulose nanofibril films with free carboxyl groups. Carbohydr Polym 84: 579-583.
9. Fukuzumi H, Saito T, Iwata T, Kumamoto Y, Isogai A (2009) Transparent and high gas barrier films of cellulose nanofibers prepared by TEMPO-mediated oxidation. Biomacromolecules 10: 162-165.
10. 13C CP-MAS NMR. Carbohydr Polym 40: 115-124.
11. Hirota M, Furihata K, Saito T, Kawada T, Isogai A (2010) Glucose/glucuronic acid alternating co-polysaccharides prepared from TEMPO-oxidized native celluloses by surface peeling. Angew Chem Int Ed 49: 7670-7672.
12. Isogai A, Saito T, Fukuzumi H (2011) TEMPO-oxidized cellulose nanofibers. Nanoscale 3: 71-85.
13. Iwatake A, Nogi M, Yano H (2008) Cellulose nanofiber-reinforced polylactic acid. Compos Sci Technol 68: 2103-2106.
14. Khorana HG (1953) The chemistry of carbodiimides. Chem Rev 53: 145-166.
15. Kim DY, Nishiyama Y, Kuga S (2002) Surface acetylation of bacterial cellulose. Cellulose 9: 361-367.
16. Lasseuguette E (2008) Grafting onto microfibrils of native cellulose. Cellulose 15: 571-580.
17. Mohanty AK, Misra M, Drzal LT (2002) Sustainable bio-composites from renewable resources: opportunities and challenges in the green materials world. J Polym Environ 10: 19-26.
18. Okita Y, Saito T, Isogai A (2010) Entire surface oxidation of various cellulose microfibrils by TEMPO-mediated oxidation. Biomacromolecules 11: 1696-1700.
19. Okita Y, Fujisawa S, Saito T, Isogai A (2011) TEMPO-oxidized cellulose nanofibrils dispersed in organic solvents. Biomacromolecules 12: 518-522.
20. Saito T, Nishiyama Y, Putaux JL, Vignon M, Isogai A (2006) Homogeneous suspensions of individualized microfibrils from TEMPO-catalyzed oxidation of native cellulose. Biomacromolecules 7: 1687-1691.
21. Saito T, Kimura S, Nishiyama Y, Isogai A (2007) Cellulose nanofibers prepared by TEMPO-mediated oxidationof native cellulose. Biomacromolecules 8: 2485-2491.
22. Saito T, Hirota M, Tamura N, Kimura S, Fukuzumi H, Heux L, Isogai A (2009) Individualization of nano-sized plant cellulose fibrils by direct surface carboxylation using TEMPO catalyst under neutral conditions. Biomacromolecules 1: 1992-1996.
23. Sheehan JC, Hess GP (1955) A new method of forming peptide bonds. J Am Chem Soc 77: 1067-1068.
24. Siqueira G, Bras J, Dufresne A (2009) New process of chemical grafting of cellulose nanoparticles with a long chain isocyanate. Langmuir 26: 402-411.
25. Smith M, Moffatt JG, Khorana HG (1958) Carbodiimides 8. Observations on the reactions of carbodiimides with acids and some new applications in the synthesis of phosphoric acid esters. J Am Chem Soc 80: 6204-6212.
26. Viëtor RJ, Newman RH, Ha MA, Apperley DC, Jarvis MC (2002) Conformational features of crystal-surface cellulose from higher plants. Plant J 30: 721-731.
27. Yokum TS, Alsina J, Barany G (2000) Solid-phase syntheses of heterocycles containing the 2-aminothiophenol moiety. J Comb Chem 2: 282-292.