Abstract
Attempts to modify the surface of oxidized cellulose microfibrils were made using amine terminated molecules. First, native cellulose was oxidized with catalytic amounts of 2,2,6,6-tetramethylpiperidine-1-oxyl radical (TEMPO), sodium hypochlorite and sodium bromide in water. The primary alcohol moieties were selectively oxidized into carboxyl groups. Then, the oxidized cellulose was coupled with amines derivatives by a peptidic reaction by using carbodiimide and hydroxysuccimide as catalyst and amidation agent. The obtained coupled cellulose showed low polarity, with stability in non-polar solvents. The products were characterized by FTIR, 13C NMR, rheology and conductometric titration as well as transmission electron microscopy. Their hydrophobic character was evaluated by observing their behavior in polar and non-polar solvents.
Similar content being viewed by others
References
Abdelmouleh M, Boufi S, ben Salah A, Belgacem MN, Gandini A (2002) Interaction of silane coupling agents with cellulose. Langmuir 18:3203–3208
Araki J, Wada M, Kuga S (2001) Steric stabilization of a cellulose microcrystal suspension by poly(ethylene glycol) grafting. Langmuir 17:21–27
Azizi Samir MAS, Alloin F, Dufresne A (2005) Review of recent research into cellulosic whiskers, their properties and their application in nanocomposite field. Biomacromolecules 6:612–626
Bragd PL, van Bekkum H, Besemer AC (2004) TEMPO-mediated oxidation of polysaccharides: survey of methods and applications. Top Catal 27:49–66
Bulpitt P, Aeschlimann D (1999) New strategy for chemical modification of hyaluronic acid: preparation of functionalized derivatives and their use in the formation of novel biocompatible hydrogels. J Biomed Mater Res 47:152–169
Chanzy H (1990) Aspects of cellulose structure. In: Kennedy JF, Phillips GO, Williams PA (eds) Cellulose sources and exploitation. Ellis Horwood Ltd., NY, pp 3–12
da Silva Perez D, Montanari S, Vignon MR (2003) TEMPO-mediated oxidation of cellulose III. Biomacromolecules 4:1417–1425
de Nooy AEJ, Besemer AC, van Bekkum H (1995) Highly selective nitroxyl radical-mediated oxidation of primary alcohol groups in water-soluble glucans. Carbohydr Res 269:89–98
Heux L, Dinand E, Vignon MR (1999) Structural aspects in ultrathin cellulose microfibrils followed by 13C CP-MAS NMR. Carbohydr Polym 40:115–124
Ichazo MN, Albano C, González J, Perera R, Candal MV (2001) Polypropylene/wood flour composites: treatments and properties. Compos Struct 54:207–214
Isogai A, Kato Y (1998) Preparation of polyuronic acid from cellulose by TEMPO-mediated oxidation. Cellulose 5:153–164
Lasseuguette E, Roux D, Nishiyama Y (2007) Rheological properties of microfibrillar suspension of TEMPO oxidized pulp. Cellulose. doi:10.1007/s10570-007-9184-2
Mahlberg R, Niemi HE-M, Denes F, Rowell RM (1998) Effect of oxygen and hexamethyldisiloxane plasma on morphology, wettability and adhesion properties of polypropylene and lignocellulosics. Int J Adhes Adhes 18:283–297
Mohanty AK, Khan MA, Hinrichsen G (2000) Influence of chemical surface modification on the properties of biodegradable jute fabrics-polyester amide composites. Composites Part A 31:143–150
Montanari S, Roumani M, Heux L, Vignon MR (2005) Topochemistry of carboxylated cellulose nanocrystals resulting from TEMPO-mediated oxidation. Macromolecules 38:1665–1691
Nitz H, Semke H, Landers R, Mülhaupt R (2001) Reactive extrusion of polycaprolactone compounds containing wood flour and lignin. J Appl Polym Sci 81:1972–1984
Orts WJ, Shey J, Imam SH, Glenn GM, Guttman ME, Revol JF (2005) Application of cellulose microfibrils in polymer nanocomposites. J Polym Environ 13:301–306
Saito T, Nishiyama Y, Putaux JL, Vignon MR, Isogai A (2006) Homogeneous suspensions of individualized microfibrils from TEMPO-catalyzed oxidation of native cellulose. Biomacromolecules 7:1687–1691
Tserki V, Zafeiropoulos NE, Simon F, Panayiotou C (2005) A study of the effect of acetylation and propionylation surface treatments on natural fibers. Composites Part A 36:1110–1118
Valadez-Gonzalez A, Cervantes-Uc JM, Olayo R, Herrera-Franco PJ (1999) Chemical modification of henequén fibers with an organosilane coupling agent. Composites Part B 30:321–331
Yuan H, Nishiyama Y, Wada M, Kuga S (2006) Surface acylation of cellulose whiskers by drying aqueous emulsion. Biomacromolecules 7:696–700
Zafeiropoulos NE, Williams DR, Baillie CA, Matthews FL (2002) Engineering and characterisation of the interface in flax fibre/polypropylene composite materials. Part I. Development and investigation of surface treatments. Composites Part A 33:1083–1093
Acknowledgments
We thank Dr. Laurent Heux and Dr. Jean-Luc Puteaux of CERMAV for respectively 13C NMR and TEM experiments.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Lasseuguette, E. Grafting onto microfibrils of native cellulose. Cellulose 15, 571–580 (2008). https://doi.org/10.1007/s10570-008-9200-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10570-008-9200-1