journal article·2014-05Open access

Effect of methylimidazole on cellulose/ionic liquid solutions and regenerated material therefrom

Carina Olsson, Artur Hedlund, Alexander Idström, Gunnar Westman

Journal of Materials Science· Volume 49· Issue 9

Abstract

Cellulose, especially wood-based cellulose, is increasingly important for making everyday materials such as man-made-regenerated textile fibers, produced via dissolution and subsequent precipitation. In this paper, the effect of cosolvents in ionic liquid-facilitated cellulose dissolution is discussed. Both microcrystalline cellulose and dissolving grade hardwood pulp were studied. Three different cosolvents in combination with ionic liquid were evaluated using turbidity measurements and viscosity. The ionic liquid precursor N-methylimidazole proved to be a promising cosolvent candidate and was thus selected for further studies together with the ionic liquid 1-ethyl-3-methylimidazolium acetate. Results show that dissolution rate can be increased by cosolvent addition, and the viscosity can be significantly reduced. The solutions were stable over time at room temperature and could be converted to regenerated textile fibers with good mechanical properties via airgap spinning and traditional wet spinning. Fibers spun from binary solvents exhibited significantly higher crystallinity than the fibers from neat ionic liquid.
Source: openalex_inverted_index · Quality: baseline

Research context

OpenAlex topics: Advanced Cellulose Research Studies · Lignin and Wood Chemistry · Dyeing and Modifying Textile Fibers

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (42)

Show source-provided references
1. Lindman B, Karlström G, Stigsson L (2010) On the mechanism of dissolution of cellulose. J Mol Liq 156:76–8110.1016/j.molliq.2010.04.016 ↗
2. Biermann O, Hädicke E, Koltzenburg S, Müller-Plathe F (2001) Hydrophilicity and lipophilicity of cellulose crystal surfaces. Angew Chem Int Ed 40:3822–382510.1002/1521-3773(20011015)40:20<3822::AID-ANIE3822>3.0.CO;2-V ↗
3. Meindersma GW, Maase M, Haan ABD (2007) Ionic liquids. In: Ullman Encyclopedia, (online encyclopedia) p. 1–3310.1002/14356007.l14_l01 ↗
4. Forsyth SA, Pringle JM, MacFarlane DR (2004) Ionic liquids: an overview. Aust J Chem 57:113–11910.1071/CH03231 ↗
5. Zavrel M, Bross D, Funke M, Büchs J, Spiess AC (2009) High-throughput screening for ionic liquids dissolving (ligno-) cellulose. Bioresour Technol 100:2580–258710.1016/j.biortech.2008.11.052 ↗
6. Hauru LKJ, Hummel M, King AWT, Kilpeläinen I, Sixta H (2012) Role of solvent parameters in the regeneration of cellulose from ionic liquid solutions. Biomacromolecules 13:2896–290510.1021/bm300912y ↗
7. Budtova T, Egal M, Gavillon R, Gericke M, Heinze T, Liebert T, Roy C, Schlufter K, Navard P (2010) Comparison of solution-state properties of cellulose dissolved in NaOH/water and in ionic liquid (EMIMAc). In: Liebert T, Heinze T, Edgar KJ (eds) Cellulose solvents: for analysis, shaping and chemical modification. American Chemical Society, Washington, pp 179–19610.1021/bk-2010-1033.ch010 ↗
8. Swatloski RP, Spear SK, Holbrey JD, Rogers RD (2002) Dissolution of cellose with ionic liquids. J Am Chem Soc 124:4974–497510.1021/ja025790m ↗
9. Viswanathan G, Murugesan S, Pushpraj V, Nalamasu O, Ajayan PM, Linhardt RJ (2006) Preparation of biopolymer fibers by electrospinning from room temperature ionic liquids. Biomacromolecules 7:415–41810.1021/bm050837s ↗
10. Kosan B, Michels C, Meister F (2008) Dissolution and forming of cellulose with ionic liquids. Cellulose 15:59–6610.1007/s10570-007-9160-x ↗
11. Wu J, Zhang J, Zhang H, He J, Ren Q, Guo M (2004) Homogeneous acetylation of cellulose in a new ionic liquid. Biomacromolecules 5:266–26810.1021/bm034398d ↗
12. Heinze T, Schwikal K, Barthel S (2005) Ionic liquids as reaction medium in cellulose functionalization. Macromol Biosci 5:520–52510.1002/mabi.200500039 ↗
13. Kilpeläinen I, Xie H, King A, Granstrom M, Heikkinen S, Argyropoulus DS (2007) Dissolution of wood in ionic liquids. Agric Food Chem 55:9142–914810.1021/jf071692e ↗
14. Fort DA, Remsing RC, Swatloski RP, Moyna P, Rogers GMRD (2007) Can ionic liquids dissolve wood? Processing and analysis of lignocellulosic materials with 1-N-butyl-3-methylimidazolium chloride. Green Chem 9:63–6910.1039/B607614A ↗
15. Sun N, Rahman M, Qin Y, Maxim ML, Rodriguez H, Rogers RD (2009) Complete dissolution and partial delignification of wood in the ionic liquid 1-ethyl-3-methylimidazolium acetate. Green Chem 11:646–65510.1039/b822702k ↗
16. Heinze T, Dorn S, Schöbitz M, Liebert T, Köhler S, Meister F (2008) Interactions of ionic liquids with polysaccharides—2: cellulose. Macromol Sympos 262:8–2210.1002/masy.200850202 ↗
17. Ebner G, Schiehser S, Potthast A, Rosenau T (2008) Side reaction of cellulose with common 1-alkyl-3-methylimidazolium-based ionic liquids. Tetrahedron Lett 49:7322–732410.1016/j.tetlet.2008.10.052 ↗
18. Liebert T (2008) Innovative concepts for the shaping and modification of cellulose. Macromol Symp 262:28–3810.1002/masy.200850204 ↗
19. Froschauer C, Hummel M, Iakovlev M, Roselli A, Schottenberger H, Sixta H (2013) Separation of hemicellulose and cellulose from wood pulp by means of ionic liquid/cosolvent systems. Biomacromolecules 14:1741–175010.1021/bm400106h ↗
20. Gericke M, Liebert T, El SOA, Heinze T (2011) Tailored media for homogeneous cellulose chemistry: ionic liquid/co-solvent mixtures. Macromol Mater Eng 296:483–49310.1002/mame.201000330 ↗
21. Gericke M, Schaller J, Liebert T, Fardim P, Meister F, Heinze T (2012) Studies on the tosylation of cellulose in mixtures of ionic liquids and a co-solvent. Carbohydr Polym 89:526–53610.1016/j.carbpol.2012.03.040 ↗
22. Gericke M, Liebert T, Heinze T (2009) Interaction of ionic liquids with polysaccharides, 8—synthesis of cellulose sulfates suitable for polyelectrolyte complex formation. Macromol Biosci 9:343–35310.1002/mabi.200800329 ↗
23. Härdelin L, Thunberg J, Perzon E, Westman G, Walkenström P, Gatenholm P (2012) Electrospinning of cellulose nanofibers from ionic liquids: the effect of different cosolvents. J Appl Polym Sci 125:1901–190910.1002/app.36323 ↗
24. Vitz J, Yevlampieva NP, Rjumtsev E, Schubert US (2010) Cellulose molecular properties in 1-alkyl-3-methylimidazolium-based ionic liquid mixtures with pyridine. Carbohydr Polym 82:1046–105310.1016/j.carbpol.2010.06.016 ↗
25. Rinaldi R (2011) Instantaneous dissolution of cellulose in organic electrolyte solutions. Chem Commun 47:511–51310.1039/C0CC02421J ↗
26. Liu Z, Wang H, Li Z, Lu X, Zhang X, Zhang S, Zhou K (2011) Characterization of the regenerated cellulose films in ionic liquids and rheological properties of the solutions. Mater Chem Phys 128:220–22710.1016/j.matchemphys.2011.02.062 ↗
27. Köhler S, Liebert T, Heinze T (2008) Interactions of ionic liquids with polysaccharides. VI pure cellulose nanoparticles from trimethylsilyl cellulose synthesized in ionic liquids. J Polym Sci Part A 46:4070–408010.1002/pola.22749 ↗
28. Mormann W, Wezstein M (2009) Trimethylsilylation of cellulose in ionic liquids. Macromol Biosci 9:369–37510.1002/mabi.200800192 ↗
29. Gericke M, Schlufter K, Liebert T, Heinze T, Budtova T (2009) Rheological properties of cellulose/ionic liquid solutions: from dilute to concentrated states. Biomacromolecules 10:1188–119410.1021/bm801430x ↗
30. Sescousse R, Le KA, Ries ME, Budtova T (2010) Viscosity of cellulose-imidazolium-based ionic liquid solutions. J Phys Chem B 114:7222–722810.1021/jp1024203 ↗
31. Idström A, Brelid H, Nydén M, Nordstierna L (2013) CP/MAS 13C NMR study of pulp hornification using nanocrystalline cellulose as a model system. Carbohydr Polym 92:881–88410.1016/j.carbpol.2012.09.097 ↗
32. Navard P, Wendler F, Meister F, Bercea M, Budtova T (2012) Preparation and properties of cellulose solutions. In: Navard P (ed) The European Polysaccharide Network of Excellence (EPNOE): research initiatives and results. Springer, Vienna, pp 91–152 Google eBook10.1007/978-3-7091-0421-7_5 ↗
33. Lovell CS, Walker A, Damion RA, Radhi A, Tanner SF, Budtova T, Ries ME (2010) Influence of cellulose on ion diffusivity in 1-ethyl-3-methyl-imidazolium acetate cellulose solutions. Biomacromolecules 11:2927–293510.1021/bm1006807 ↗
34. Kwei TK (1979) Macromolecules in solution. In: Bovey FA, Winslow FH (eds) Macromolecules. An introduction to polymer science. Academic Press, Inc, New York, pp 273–316
35. Le K, Sescousse R, Budtova T (2012) Influence of water on cellulose-EMIMAc solution properties: a viscometric study. Cellulose 19:45–5410.1007/s10570-011-9610-3 ↗
36. Chen M, Bomble YJ, Himmel ME, Brady JW (2012) Molecular dynamics simulations of the interaction of glucose with imidazole in aqueous solution. Carbohydr Res 349:73–7710.1016/j.carres.2011.12.008 ↗
37. Cho HM, Gross AS, Chu J-W (2011) Dissecting force interactions in cellulose deconstruction reveals the required solvent versatility for overcoming biomass recalcitrance. J Am Chem Soc 133:14033–1404110.1021/ja2046155 ↗
38. Röder T, Moosbauer J, Wöss K, Schlader S, Kraft G (2013) Man-made cellulose fibres—a comparison based on morphology and mechanical properties. Lenzinger Berichte 91:7–12
39. Zuckerstätter G, Terinte N, Sixta H, Schuster KC (2013) Novel insight into cellulose supramolecular structure through 13C CP-MAS NMR spectroscopy and paramagnetic relaxation enhancement. Carbohydr Polym 93:122–12810.1016/j.carbpol.2012.05.019 ↗
40. Newman R, Davidson T (2004) Molecular conformations at the cellulose–water interface. Cellulose 11:23–3210.1023/B:CELL.0000014778.49291.c6 ↗
41. Ibbett RN, Domvoglou D, Fasching M (2007) Characterisation of the supramolecular structure of chemically and physically modified regenerated cellulosic fibres by means of high-resolution carbon-13 solid-state NMR. Polymer 48:1287–129610.1016/j.polymer.2006.12.034 ↗
42. King AWT, Parviainen A, Karhunen P, Matikainen J, Hauru LKJ, Sixta H, Kilpelainen I (2012) Relative and inherent reactivities of imidazolium-based ionic liquids: the implications for lignocellulose processing applications. RSC Adv 2:8020–802610.1039/c2ra21287k ↗