Abstract
Cellulose, a fascinating biopolymer and the most common organic compound on earth, is comprehensively reviewed. Details of its crystalline phases are given, starting with a description of molecular and supramolecular structures, including the hydrogen bond systems. Sources of this ubiquitous biopolymer are mentioned, with attention to the special properties of bacterially synthesized nanofibrous cellulose. Nanostructures obtained by disintegration of cellulose fibers (top-down approach) yielding nano- or microfibrillated cellulose and cellulose whiskers are the basis for novel materials with extraordinary properties. Moreover, nanofibers and nanoparticles can be made by special techniques applying the bottom-up approach. Efficient systems to dissolve cellulose by destruction of the hydrogen bond systems using ionic liquids and systems based on polar aprotic solvent and salt are described. Novel cellulose derivatives are available by chemical modification under heterogeneous or homogeneous conditions, depending on the cellulose reactivity. In particular, unconventional nucleophilic displacement reactions yielding products for high-value applications are highlighted. Novel amino cellulose derivatives showing fully reversible aggregation behavior and nanostructure formation on various materials are the focus of interest. Finally, “click chemistry” for the synthesis of novel cellulose derivatives is discussed.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Similar content being viewed by others
References
Klemm D, Heublein B, Fink H-P et al (2005) Cellulose: fascinating biopolymer and sustainable raw material. Angew Chem Int Ed 44:3358–3393
Mohanty AK, Misra M, Hinrichsen G (2000) Biofibres, biodegradable polymers and biocomposites. An overview. Macromol Mater Eng 276(277):1–24
Heinze T, Liebert T (2012) Celluloses and polyoses/hemicelluloses. In: Matyjaszewski K, Möller M (eds) Polymer science: a comprehensive reference, vol 10. Elsevier, Amsterdam, pp 83–152
Payen A (1839) Composition de la matière ligneuse. Comptes Rendus 8:51–53
Young RA (1994) Comparison of the properties of chemical cellulose pulps. Cellulose 1:107–130
Sixta H (ed) (2006) Handbook of pulp. Wiley-VCH, Weinheim
Schubert S, Schlufter K, Heinze T (2011) Configurations, structures, and morphologies of cellulose. In: Popa V (ed) Polysaccharides in medicinal and pharmaceutical applications. iSmithers, Shrewsbury, pp 1–55
Hon DN-S (1996) Cellulose and its derivatives: structures, reactions, and medical uses. In: Dumitriu S (ed) Polysaccharides in medical applications. Marcel Dekker, New York, pp 87–105
Eichhorn SJ, Baillie CA, Zafeiropoulos N et al (2001) Current international research into cellulosic fibers and composites. J Mater Sci 36:2107–2131
Vandamme EJ, De Baets S, Vanbaelen A et al (1998) Improved production of bacterial cellulose and its application potential. Polym Degrad Stab 59:93–99
Jonas R, Farah LF (1998) Production and application of microbial cellulose. Polym Degrad Stab 59:101–106
Rao VSR, Sundararajan PR, Ramakrishnan C et al (1967) Conformational studies of amylose. In: Ramachandran GN (ed) Conformation of biopolymers, vol 2. Academic, London, pp 721–737
Krässig HA (1993) Cellulose: structure, accessibility and reactivity. Gordon and Breach Science, Yverdon
Perez S, Mazeau K (2005) Conformations, structures, and morphologies of celluloses. In: Dumitriu S (ed) Polysaccharides: structural diversity and functional versatility. Marcel Dekker, New York, pp 41–68
Kondo T (1997) The relationship between intramolecular hydrogen bonds and certain physical properties of regioselectively substituted cellulose derivatives. J Polym Sci A Polym Chem 35:717–723
Liang CY, Marchessault RH (1959) Infrared spectra of crystalline polysaccharides. I. Hydrogen bonds in native celluloses. J Polym Sci 37:385–395
Michell AJ (1988) Second derivative FTIR spectra of celluloses I and II and related mono- and oligosaccharides. Carbohydr Res 173:185–195
Kamide K, Okajima K, Kowsaka K et al (1985) CP/MASS (cross-polarization/magic angle sample spinning] carbon-13 NMR spectra of cellulose solids: an explanation by the intramolecular hydrogen bond concept. Polym J 17:701–706
Gardner KH, Blackwell J (1974) Structure of native cellulose. Biopolymers 13:1975–2001
Nishiyama Y, Langan P, Chanzy H (2002) Crystal structure and hydrogen-bonding system in cellulose Iβ from synchrotron x-ray and neutron fiber diffraction. J Am Chem Soc 124:9074–9082
Kondo T (2005) Hydrogen bonds in cellulose and cellulose derivatives. In: Dumitriu S (ed) Polysaccharides: structural diversity and functional versatility, 2nd edn. Marcel Dekker, New York, pp 69–98
Tashiro K, Kobayashi M (1991) Theoretical evaluation of three-dimensional elastic constants of native and regenerated celluloses: role of hydrogen bonds. Polymer 32:1516–1526
Sarko A, Muggli R (1947) Packing analysis of carbohydrates and polysaccharides. III. Valonia cellulose and cellulose II. Macromolecules 7:486–494
Atalla RH, VanderHart DL (1984) Native cellulose: a composite of two distinct crystalline forms. Science 223:283–285
Isogai A, Usuda M, Kato T et al (1989) Solid-state CP/MAS carbon-13 NMR study of cellulose polymorphs. Macromolecules 22:3168–3172
Zugenmaier P (2001) Conformation and packing of various crystalline cellulose fibers. Prog Polym Sci 26:1341–1417
Langan P, Nishiyama Y, Chanzy H (1999) A revised structure and hydrogen-bonding system in cellulose II from a neutron fiber diffraction analysis. J Am Chem Soc 121:9940–9946
Wada M, Heux L, Isogai A et al (2001) Improved structural data of cellulose IIII prepared in supercritical ammonia. Macromolecules 34:1237–1243
Gardiner ES, Sarko A (1985) Packing analysis of carbohydrates and polysaccharides. 16. The crystal structures of celluloses IVI and IVII. Can J Chem 63:173–180
Isogai A (1994) Allomorphs of cellulose and other polysaccharides. In: Gilbert RD (ed) Cellulosic polymers: blends and composites. Hanser, Munich, p 1
Hermans PH, Weidinger A (1946) Recrystallization of amorphous cellulose. J Am Chem Soc 68:1138
Wadehra IL, Manley RSJ (1965) Recrystallization of amorphous cellulose. J Appl Polym Sci 9:2627–2630
Schroeder LR, Gentile VM, Atalla RH (1986) Nondegradative preparation of amorphous cellulose. J Wood Chem Technol 6:1–14
Atalla RH, Ellis JD, Schroeder LR (1984) Some effects of elevated temperatures on the structure of cellulose and its transformation. J Wood Chem Technol 4:465–482
de Souza Lima MM, Borsali R (2004) Rodlike cellulose microcrystals: structure, properties, and applications. Macromol Rapid Commun 25:771–787
Ioelovich M, Leykin A (2008) Cellulose as a nanostructured polymer: a short review. Bioresources 3:1403–1418
Welch LM, Roseveare WE, Mark H (1946) Fibrillar structure of rayon fibers. Ind Eng Chem 38:580–582
Sisson WA (1940) X-ray studies of crystallite orientation in cellulose fibers. III. Fiber structures from coagulated cellulose. J Phys Chem 44:513–529
Klemm D, Schumann D, Udhardt U et al (2001) Bacterial synthesized cellulose – artificial blood vessels for microsurgery. Prog Polym Sci 26:1561–1603
Yoshinaga F, Tonouchi N, Watanabe K (1997) Research progress in the production of bacterial cellulose by aeration and agitation culture and its application as a new industrial material. Biosci Biotechnol Biochem 61:219–224
Kongruang S (2008) Bacterial cellulose production by Acetobacter xylinum strains from agricultural waste products. Appl Biochem Biotechnol 148:245–256
Ring DF, Nashed W, Dow T (1987) Microbial polysaccharide articles and methods of production. US Patent 4,655,758, 7 Apr 1987
Ring DF, Nashed W, Dow T (1986) Liquid loaded pad for medical applications. US Patent 4,588,400, 13 May 1986
Farah LF (1990) Process for the preparation of cellulose film, cellulose film produced thereby, artificial skin graft and its use. US Patent 4,912,049, 27 Mar 1990
Czaja W, Krystynowicz A, Bielecki S et al (2006) Microbial cellulose-the natural power to heal wounds. Biomaterials 27:145–151
Watanabe K, Tabuchi M, Morinaga Y et al (1998) Structural features and properties of bacterial cellulose produced in agitated-culture. Cellulose 5:187–200
Klemm D, Schumann D, Kramer F et al (2006) Nanocelluloses as innovative polymers in research and application. Adv Polym Sci 205:49–96
Pääkköö M, Ankerfors M, Kosonen H et al (2007) Enzymatic hydrolysis combined with mechanical shearing and high-pressure homogenization for nanoscale cellulose fibrils and strong gels. Biomacromolecules 8:1934–1941
Samir MASA, Alloin F, Dufresne A (2005) Review of recent research into cellulosic whiskers, their properties and their application in nanocomposite field. Biomacromolecules 6:612–626
Dufresne A (2008) Polysaccharide nano crystal reinforced nanocomposites. Can J Chem 86:484–494
Steege H-H, Philipp B (1974) Production, characterization, and use of microcrystalline cellulose. Zellst Pap 23:68–73
Bondeson D, Mathew A, Oksman K (2006) Optimization of the isolation of nanocrystals from microcrystalline cellulose by acid hydrolysis. Cellulose 13:171–180
Araki J, Wada M, Kuga S et al (1998) Flow properties of microcrystalline cellulose suspension prepared by acid treatment of native cellulose. Colloid Surf A Physicochem Eng Asp 142:75–82
Dong XM, Revol JF, Gray DG (1998) Effect of microcrystallite preparation conditions on the formation of colloid crystals of cellulose. Cellulose 5:19–32
Araki J, Wada M, Kuga S et al (1999) Influence of surface charge on viscosity behavior of cellulose microcrystal suspension. J Wood Sci 45:258–261
de Vries HI (1951) Rotatory power and other optical properties of certain liquid crystals. Acta Crystallogr 4:219–226
Revol J-F, Bradford H, Giasson J et al (1992) Helicoidal self-ordering of cellulose microfibrils in aqueous suspension. Int J Biol Macromol 14:170–172
Kroon-Batenburg LMJ, Kroon J, Northolt MG (1986) Chain modulus and intramolecular hydrogen bonding in native and regenerated cellulose fibers. Polym Commun 27:290–292
Nishino T, Matsuda I, Hirao K (2004) All-cellulose composite. Macromolecules 37:7683–7687
Odijk T, Lekkerkerker HNW (1985) Theory of the isotropic-liquid crystal phase separation for a solution of bidisperse rodlike macromolecules. J Phys Chem 89:2090–2096
de Souza Lima MM, Borsali R (2002) Static and dynamic light scattering from polyelectrolyte microcrystal cellulose. Langmuir 18:992–996
Angellier H, Putaux J-L, Molina-Boisseau S et al (2005) Starch nanocrystal fillers in an acrylic polymer matrix. Macromol Symp 221:95–104
Marchessault RH, Morehead FF, Walter NM (1959) Liquid crystal systems from fibrillar polysaccharides. Nature 184:632–633
Revol JF, Godbout L, Dong XM et al (1994) Chiral nematic suspensions of cellulose crystallites; phase separation and magnetic field orientation. Liq Cryst 16:127–134
Revol JF, Godbout L, Gray DG (1998) Solid self-assembled films of cellulose with chiral nematic order and optically variable properties. J Pulp Paper Sci 24:146–149
Orts WJ, Godbout L, Marchessault RH et al (1998) Enhanced ordering of liquid crystalline suspensions of cellulose microfibrils: a small-angle neutron scattering study. Macromolecules 31:5717–5725
Favier V, Canova GR, Cavaillé JY et al (1995) Nanocomposite materials from latex and cellulose whiskers. Polym Adv Technol 6:351–355
Favier V, Chanzy H, Cavaillé JY (1995) Polymer nanocomposites reinforced by cellulose whiskers. Macromolecules 28:6365–6367
Viet D, Beck-Candanedo S, Gray DG (2007) Dispersion of cellulose nanocrystals in polar organic solvents. Cellulose 14:109–113
Dubief D, Samain E, Dufresne A (1999) Polysaccharide microcrystals reinforced amorphous poly(β-hydroxyoctanoate) nanocomposite materials. Macromolecules 32:5765–5771
Dufresne A, Kellerhals MB, Witholt B (1999) Transcrystallization in Mcl-PHAs/cellulose whiskers composites. Macromolecules 32:7396–7401
Angles NM, Dufresne A (2000) Plasticized starch/tunicin whiskers nanocomposites. 1. Structural analyses. Macromolecules 33:8344–8353
Grunert M, Winter WT (2002) Nanocomposites of cellulose acetate butyrate reinforced with cellulose nanocrystals. J Polym Environ 10:27–30
Chazeau L, Cavaillé JY, Perez J (2000) Plasticized PVC reinforced with cellulose whiskers. II. Plastic behavior. J Polym Sci B Polym Phys 38:383–392
Revol JF (1982) On the cross-sectional shape of cellulose crystallites in Valonia ventricosa. Carbohydr Polym 2:123–134
Correa AC, Morais Teixeira E, Carmona VB et al (2014) Obtaining nanocomposites of polyamide 6 and cellulose whiskers via extrusion and injection molding. Cellulose 21:311–322
Mathew AP, Dufresne A (2002) Morphological investigation of nanocomposites from sorbitol plasticized starch and tunicin whiskers. Biomacromolecules 3:609–617
Turbak AF, Snyder FW, Sandberg KR (1982) Suspensions containing microfibrillated cellulose. EP 19810108847, 12 May 1982
Wagberg L, Decher G, Norgren M et al (2008) The build-up of polyelectrolyte multilayers of microfibrillated cellulose and cationic polyelectrolytes. Langmuir 24:784–795
Li Y, Li G, Zou Y et al (2014) Preparation and characterization of cellulose nanofibers from partly mercerized cotton by mixed acid hydrolysis. Cellulose 21:301–309
Werner O, Persson L, Nolte M et al (2008) Patterning of surfaces with nanosized cellulosic fibrils using microcontact printing and a lift-off technique. Soft Matter 4:1158–1160
Siqueira G, Bras J, Dufresne A (2009) Cellulose whiskers versus microfibrils: influence of the nature of the nanoparticle and its surface functionalization on the thermal and mechanical properties of nanocomposites. Biomacromolecules 10:425–432
Stenstad P, Andresen M, Tanem BS et al (2008) Chemical surface modifications of microfibrillated cellulose. Cellulose 15:35–45
Dong S, Sapieha S, Schreiber HP (1993) Mechanical properties of corona-modified cellulose/polyethylene composites. Polym Eng Sci 33:343–346
Cavaille JY, Chanzy H, Fleury E et al (1997) Surface-modified cellulose microfibrils, method for making the same, and use thereof as a filler in composite material. US Patent 6,117,545, 12 Sept 2000
Cash MJ, Chan AN, Conner HT et al (1999) Derivatized microfibrillar polysaccharide. US Patent 6,602,994, 5 Aug 2003
Gousse C, Chanzy H, Excoffier G et al (2002) Stable suspensions of partially silylated cellulose whiskers dispersed in organic solvents. Polymer 43:2645–2651
Agarwal M, Lvov Y, Varahramyan K (2006) Conductive wood microfibres for smart paper through layer-by-layer nanocoating. Nanotechnology 17:5319–5325
Greiner A, Wendorff JH (2007) Electrospinning: a fascinating method for the preparation of ultrathin fibers. Angew Chem Int Ed 46:5670
Reneker DH, Chun I (1996) Nanometer diameter fibers of polymer, produced by electrospinning. Nanotechnology 7:216–223
Frenot A, Chronakis IS (2003) Polymer nanofibers assembled by electrospinning. Curr Opin Colloid Interface Sci 8:64–75
Xie J, Li X, Xia Y (2008) Putting electrospun nanofibers to work for biomedical research. Macromol Rapid Commun 29:1775–1792
Li F, Zhao Y, Song Y (2010) Core-shell nanofibers: nano channel and capsule by coaxial electrospinning. In: Kumar A (ed) Nanofibers. InTech, Rijeka, pp 419–438
Scholten E, Bromberg L, Rutledge GC, Hatton TA (2011) Electrospun polyurethane fibers for absorption of volatile organic compounds from air. ACS Appl Mater Interfaces 10:3902–3909
Kim C-W, Kim D-S, Kang S-Y et al (2006) Structural studies of electrospun cellulose nanofibers. Polymer 47:5097–5107
Viswanathan G, Murugesan S, Pushparaj V et al (2006) Preparation of biopolymer fibers by electrospinning from room temperature ionic liquids. Biomacromolecules 7:415–418
Qi H, Sui X, Yuan J et al (2010) Electrospinning of cellulose-based fibers from NaOH/urea aqueous system. Macromol Mater Eng 295:695–700
Römhild K, Wiegand C, Hipler UC et al (2013) Novel bioactive amino-functionalized cellulose nanofibers. Macromol Rapid Commun 34:1767–1771
Hornig S, Heinze T (2008) Efficient approach to design stable water-dispersible nanoparticles of hydrophobic cellulose esters. Biomacromolecules 9:1487–1492
Wondraczek H, Petzold-Welcke K, Fardim P et al (2013) Nanoparticles from conventional cellulose esters: evaluation of preparation methods. Cellulose 20:751–760
Nikolajski M, Wotschadlo J, Clement JH et al (2012) Amino-functionalized cellulose nanoparticles: preparation, characterization, andinteractions with living cells. Macromol Biosci 12:920–925
Kostag M, Köhler S, Liebert T et al (2010) Pure cellulose nanoparticles from trimethylsilyl cellulose. Macromol Symp 294(2):96–106
Liebert T, Kostag M, Wotschadlo J et al (2011) Stable cellulose nanospheres for cellular uptake. Macromol Biosci 11:1387–1392
Heinze T, Liebert T (2001) Unconventional methods in cellulose functionalization. Prog Polym Sci 26:1689–1762
Heinze T, Dicke R, Koschella A et al (2000) Effective preparation of cellulose derivatives in a new simple cellulose solvent. Macromol Chem Phys 201:627–631
El Seoud OA, Heinze T (2005) Organic esters of cellulose: new perspectives for old polymers. In: Heinze T (ed) Polysaccharides I, structure, characterization and use, vol 186, Advances in polymer science. Springer, Berlin, pp 103–149
Morgenstern B, Berger W (1993) Investigations about dissolution of cellulose in the lithium chloride/N, N-dimethylformamide system. Acta Polym 44:100–102
Silva AA, Laver ML (1997) Molecular weight characterization of wood pulp cellulose: dissolution and size exclusion chromatographic analysis. Tappi J 80:173–180
Striegel A (1998) Theory and applications of DMAc/LiCl in the analysis of polysaccharides. Carbohydr Polym 34:267–274
Kostag M, Liebert T, El Seoud OA et al (2013) Efficient cellulose solvent: quaternary ammonium chlorides. Macromol Rapid Commun 34:1580–1584
Gericke M, Liebert T, El Seoud OA et al (2011) Tailored media for homogeneous cellulose chemistry: ionic liquid/co-solvent mixtures. Macromol Mater Eng 296:483–493
Berger W, Keck M, Philipp B (1988) On the mechanism of cellulose dissolution in nonaqueous solvents, especially in O-basic systems. Cellul Chem Technol 22:387–397
Ciacco GT, Liebert TF, Frollini E et al (2003) Application of the solvent dimethyl sulfoxide/tetrabutyl-ammonium fluoride trihydrate as reaction medium for the homogeneous acylation of Sisal cellulose. Cellulose 10:125–132
Sharma RK, Fry JL (1983) Instability of anhydrous tetra-n-alkylammonium fluorides. J Org Chem 48:2112–2114
Sun H, DiMagno SG (2005) Anhydrous tetrabutylammonium fluoride. J Am Chem Soc 127:2050–2051
Köhler S, Heinze T (2007) New solvents for cellulose: dimethyl sulfoxide/ammonium fluorides. Macromol Biosci 7:307–314
Casarano R, Pires PAR, El Seoud OA (2014) Acylation of cellulose in a novel solvent system: solution of dibenzyldimethylammonium fluoride in DMSO. Carbohydr Polym 101:444–450
Burchard W (1993) Macromolecular association phenomena. A neglected field of research? Trends Polym Sci 1:192–198
Schulz L, Burchard W, Dönges R (1998) Evidence of supramolecular structures of cellulose derivatives in solution. In: Heinze T, Glasser WG (eds) Cellulose derivatives: modification, characterization, and nanostructures, vol 688, ACS symposium series. American Chemical Society, Washington DC, pp 218–238
Morgenstern B, Kammer H-W (1999) On the particulate structure of cellulose solutions. Polymer 40:1299–1304
Menger FM (1993) Enzyme reactivity from an organic perspective. Acc Chem Res 26:206–212
Husemann E, Siefert E (1969) N-Ethylpyridinium chloride as solvent and reaction medium for cellulose. Makromol Chem 128:288–291
Swatloski RP, Spear SK, Holbrey JD et al (2002) Dissolution of cellulose with ionic liquids. J Am Chem Soc 24:4974–4975
Swatloski RP, Rogers RD, Holbrey JD (2003) Dissolution and processing of cellulose using ionic liquids, cellulose solution, and regenerating cellulose. World Patent 2003029329 A2, 10 April 2003
Gericke M, Fardim P, Heinze T (2012) Ionic liquids – promising but challenging solvents for homogeneous derivatization of cellulose. Molecules 17:7458–7502
El Seoud OA, Koschella A, Fidale LC et al (2007) Applications of ionic liquids in carbohydrate chemistry: a window of opportunities. Biomacromolecules 8:2629–2647
Zhu S, Wu Y, Chen Q et al (2006) Dissolution of cellulose with ionic liquids and its application: a mini-review. Green Chem 8:325–327
Barthel S, Heinze T (2006) Acylation and carbanilation of cellulose in ionic liquids. Green Chem 8:301–306
Liebert T (2008) Innovative concepts for the shaping and modification of cellulose. Macromol Symp 262:28–38
Ebner G, Schiehser S, Potthast A et al (2008) Side reaction of cellulose with common 1-alkyl-3-methylimidazolium-based ionic liquids. Tetrahedron Lett 49:7322–7324
Handy ST, Okello M (2005) The 2-position of imidazolium ionic liquids: substitution and exchange. J Org Chem 70:1915–1918
Erdmenger T, Haensch C, Hoogenboom R et al (2007) Homogeneous tritylation of cellulose in 1-butyl-3-methylimidazolium chloride. Macromol Biosci 7:440–445
Sobue H, Kiessig H, Hess K (1939) The system: cellulose-sodium hydroxide-water in relation to the temperature. Z Phys Chem B43:309–328
Isogai A, Atalla RH (1998) Dissolution of cellulose in aqueous NaOH solutions. Cellulose 5:309–319
Yamashiki T, Kamide K, Okajima K (1990) New cellulose fiber from aqueous alkali cellulose solution. In: Kennedy JF, Phillips GO, Williams PA (eds) Cellulose sources and exploitation. Ellis Horwood, London, pp 197–202
Yamashiki T, Matsui T, Saitoh M et al (1990) Characterization of cellulose treated by the steam explosion method. Part 1. Influence of cellulose resources on changes in morphology, degree of polymerization, solubility and solid structure. Br Polym J 22:73–83
Yamashiki T, Matsui T, Saitoh M et al (1990) Characterization of cellulose treated by the steam explosion method. Part 2: effect of treatment conditions on changes in morphology, degree of polymerization, solubility in aqueous sodium hydroxide, and supermolecular structure of soft wood pulp during steam explosion. Br Polym J 22:121–128
Yamashiki T, Matsui T, Saitoh M et al (1990) Characterization of cellulose treated by the steam explosion method. Part 3: effect of crystal forms (cellulose I, II and III) of original cellulose on changes in morphology, degree of polymerization, solubility and supermolecular structure by steam explosion. Br Polym J 22:201–212
Yamashiki T, Matsui T, Kowsaka K et al (1992) New class of cellulose fiber spun from the novel solution of cellulose by wet spinning method. J Appl Polym Sci 44:691–698
Zhou J, Zhang L (2000) Solubility of cellulose in sodium hydroxide/urea aqueous solution. Polym J 32:866–870
Cai J, Zhang L (2005) Rapid dissolution of cellulose in LiOH/urea and NaOH/urea aqueous solutions. Macromol Biosci 5:539–548
Cai J, Liu Y, Zhang L (2006) Dilute solution properties of cellulose in LiOH/urea aqueous system. J Polym Sci B Polym Phys 44:3093–3101
Egal M, Budtova T, Navard P (2008) The dissolution of microcrystalline cellulose in sodium hydroxide-urea aqueous solutions. Cellulose 15:361–370
Cai J, Zhang L, Liu S et al (2008) Dynamic self-assembly induced rapid dissolution of cellulose at low temperatures. Macromolecules 41:9345–9351
Cai J, Zhang L (2006) Unique gelation behavior of cellulose in NaOH/Urea aqueous solution. Biomacromolecules 7:183–189
Qi H, Chang CY, Zhang L (2008) Effects of temperature and molecular weight on dissolution of cellulose in NaOH/urea aqueous solution. Cellulose 15:779–787
Liu S, Zhang L (2009) Effects of polymer concentration and coagulation temperature on the properties of regenerated cellulose films prepared from LiOH/urea solution. Cellulose 16:189–198
Cai J, Zhang L, Chang C et al (2007) Hydrogen-bond-induced inclusion complex in aqueous cellulose/LiOH/urea solution at low temperature. ChemPhysChem 8:1572–1579
Ruan D, Lue A, Zhang L (2008) Gelation behaviors of cellulose solution dissolved in aqueous NaOH/thiourea at low temperature. Polymer 49:1027–1036
Balser K, Hoppe L, Eicher T et al (1986) Cellulose esters. In: Gerhartz W, Yamamoto YS, Campbell FT et al (eds) Ullmanns’s encyclopedia of industrial chemistry, vol A5, 5th edn. Wiley-VCH, Weinheim, p 419
Brandt L (1986) Cellulose ethers. In: Gerhartz W, Yamamoto YS, Campbell FT et al (eds) Ullmann’s encyclopedia of industrial chemistry, vol A5, 5th edn. Wiley-VCH, Weinheim, p 461
Wu J, Zhang J, Zhang H et al (2004) Homogeneous acetylation of cellulose in a new ionic liquid. Biomacromolecules 5:266–268
Klohr EA, Koch W, Klemm D et al (2000) Manufacture of regioselectively substituted esters of oligo- and polysaccharides. DE Patent 19951734, 07 Sept 2000
Ibrahim AA, Nada AMA, Hagemann U et al (1996) Preparation of dissolving pulp from sugarcane bagasse, and its acetylation under homogeneous solution condition. Holzforschung 50:221–225
Heinze T, Liebert TF, Pfeiffer KS et al (2003) Unconventional cellulose esters: synthesis, characterization, and structure property relations. Cellulose 10:283–296
Takaragi A, Minoda M, Miyamoto T et al (1999) Reaction characteristics of cellulose in the lithium chloride/1,3-dimethyl-2-imidazolidinone solvent system. Cellulose 6:93–102
Heinze T, Glasser WG (1998) The role of novel solvents and solution complexes for the preparation of highly engineered cellulose derivatives. ACS Symp Ser 688:2–18
Heinze T, Liebert T, Koschella A (2006) Esterification of polysaccharides. Springer, Berlin
Staab HA (1962) New methods of preparative organic chemistry IV. Syntheses using heterocyclic amides (azolides). Angew Chem Int Ed 1:351–367
Gericke M, Liebert T, Heinze T (2009) Interaction of ionic liquids with polysaccharides – 8. Synthesis of cellulose sulfates suitable for symplex formation. Macromol Biosci 9:343–353
Wang Z-M, Li L, Xiao K-J et al (2009) Homogeneous sulfation of bagasse cellulose in an ionic liquid and anticoagulation activity. Bioresour Technol 100:1687–1690
Gericke M, Liebert T, Heinze T (2009) Polyelectrolyte synthesis and in situ complex formation in ionic liquids. J Am Chem Soc 131:13220–13221
Petzold-Welcke K, Michaelis N, Heinze T (2009) Unconventional cellulose products through nucleophilic displacement reactions. Macromol Symp 280:72–85
Heinze T, Petzold-Welcke K (2012) Recent advances in cellulose chemistry. In: Habibi Y, Lucia LA (eds) Polysaccharide building blocks: a sustainable approach to the development of renewable biomaterials. Wiley, Hoboken, pp 1–50
Klemm D (1998) Regiocontrol in cellulose chemistry: principles and examples of etherification and esterification. In: Heinze TJ, Glasser EG (eds) Cellulose derivatives: modification, characterisation, and nanostructures, vol 688. American Chemical Society, Washington DC, pp 19–37
Wenz G, Liepold P, Bordeanu N (2005) Synthesis and SAM formation of water soluble functional carboxymethylcelluloses: thiosulfates and thioethers. Cellulose 12:85–96
Arai K, Aoki F (1994) Preparation and identification of sodium deoxycellulosesulfonate. Sen’i Gakkaishi 50:510–514
Arai K, Yoda N (1998) Preparation of water-soluble sodium deoxycellulose sulfonate from homogeneously prepared tosyl cellulose. Cellulose 5:51–58
Liu C, Baumann H (2002) Exclusive and complete introduction of amino groups and their N-sulfo and N-carboxymethyl groups into the 6-position of cellulose without the use of protecting groups. Carbohydr Res 337:1297–1307
Heinze T (1998) New ionic polymers by cellulose functionalization. Macromol Chem Phys 199:2341–2364
Koschella A, Heinze T (2001) Novel regioselectively 6-functionalized cationic cellulose polyelectrolytes prepared via cellulose sulfonates. Macromol Biosci 1:178–184
Heinze T, Koschella A, Magdaleno-Maiza L et al (2001) Nucleophilic displacement reactions on tosyl cellulose by chiral amines. Polym Bull 46:7–13
Knaus S, Mais U, Binder WH (2003) Synthesis, characterization and properties of methylaminocellulose. Cellulose 10:139–150
Tiller J, Berlin P, Klemm D (1999) Soluble and film-forming cellulose derivatives with redox-chromogenic and enzyme immobilizing 1,4-phenylenediamine groups. Macromol Chem Phys 200:1–9
Tiller J, Berlin P, Klemm D (2000) Novel matrices for biosensor application by structural design of redox-chromogenic aminocellulose esters. J Appl Polym Sci 75:904–915
Berlin P, Klemm D, Tiller J et al (2000) A novel soluble aminocellulose derivative type: its transparent film-forming properties and its efficient coupling with enzyme proteins for biosensors. Macromol Chem Phys 201:2070–2082
Berlin P, Klemm D, Jung A et al (2003) Film-forming aminocellulose derivatives as enzyme-compatible support matrices for biosensor developments. Cellulose 10:343–367
Becher J, Liebegott H, Berlin P et al (2004) Novel xylylene diaminocellulose derivatives for enzyme immobilization. Cellulose 11:119–126
Jung A, Berlin P (2005) New water-soluble and film-forming aminocellulose tosylates as enzyme support matrices with Cu2+-chelating properties. Cellulose 12:67–84
Dam J, Schuck P (2005) Sedimentation velocity analysis of heterogeneous protein-protein interactions: sedimentation coefficient distributions c(s) and asymptotic boundary profiles from Gilbert-Jenkins theory. Biophys J 89:651–666
Heinze T, Nikolajski M, Daus S et al (2011) Protein-like oligomerisation of carbohydrates. Angew Chem Int Ed 50:8602–8604
Ferrone FA, Hofrichter J, Eaton WA (1985) Kinetics of sickle hemoglobin polymerization. II. A double nucleation mechanism. J Mol Biol 183:611–631
Teif VB, Bohinc K (2011) Condensed DNA: condensing the concepts. Prog Biophys Mol Biol 105:208–222
Nikolajski M, Heinze T, Adams GG et al (2014) Protein–like fully reversible tetramerisation and super-association of an aminocellulose. Sci Rep 4:3861
Liebert T, Hänsch C, Heinze T (2006) Click chemistry with polysaccharides. Macromol Rapid Commun 27:208–213
Koschella A, Richter M, Heinze T (2010) Novel cellulose-based polyelectrolytes synthesized via the click reaction. Carbohydr Res 345:1028–1033
Pohl M, Schaller J, Meister F et al (2008) Selectively dendronized cellulose: synthesis and characterization. Macromol Rapid Commun 29:142–148
Heinze T, Schöbitz M, Pohl M et al (2008) Interactions of ionic liquids with polysaccharides: IV. Dendronization of 6-azido-6-deoxy cellulose. J Polym Sci A Polym Chem 46:3853–3859
Schöbitz M, Meister F, Heinze T (2009) Unconventional reactivity of cellulose dissolved in ionic liquids. Macromol Symp 280:102–111
Pohl M, Morris GA, Harding SE et al (2009) Studies on the molecular flexibility of novel dendronized carboxymethyl cellulose derivatives. Eur Polym J 45:1098–1110
Pohl M, Heinze T (2008) Novel biopolymer structures synthesized by dendronization of 6-deoxy-6-aminopropargyl cellulose. Macromol Rapid Commun 29:1739–1745
Fenn D, Pohl M, Heinze T (2009) Novel 3-O-propargyl cellulose as a precursor for regioselective functionalization of cellulose. React Funct Polym 69:347–352
Elschner T, Ganske K, Heinze T (2013) Synthesis and aminolysis of polysaccharide carbonates. Cellulose 20:339–353
Pourjavadi A (2011) Synthesis of soluble N-functionalized polysaccharide derivatives using phenyl carbonate precursor and their application as catalysts (Erratum to document cited in CA156:339191]. Starch 63:820
Hayashi S (2002) Synthesis and properties of cellulose carbonate derivatives. Kobunshi Ronbunshu 59:1–7
Sanchez Chaves M, Arranz F (1985) Water-insoluble dextrans by grafting, 2. Reaction of dextrans with n-alkyl chloroformates. Chemical and enzymic hydrolysis. Makromol Chem 186:17–29
Elschner T, Kötteritzsch M, Heinze T (2014) Synthesis of cellulose tricarbonates in 1-butyl-3-methylimidazolium chloride/pyridine. Macromol Biosci 14:161–165
Acknowledgements
Dr. Andreas Koschella is thankfully acknowledged for his efforts in preparing the manuscript.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2015 Springer International Publishing Switzerland
About this chapter
Cite this chapter
Heinze, T. (2015). Cellulose: Structure and Properties. In: Rojas, O. (eds) Cellulose Chemistry and Properties: Fibers, Nanocelluloses and Advanced Materials. Advances in Polymer Science, vol 271. Springer, Cham. https://doi.org/10.1007/12_2015_319
Download citation
DOI: https://doi.org/10.1007/12_2015_319
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-26013-6
Online ISBN: 978-3-319-26015-0
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)