One-pot functionalization of cellulose nanocrystals with various cationic groups
Source abstract
Abstract
After successful cationization of cellulose nanocrystals (CNCs) to produce pyridinium-grafted-CNCs, a variety of different cationic CNCs were prepared using a similar procedure, thus unlocking access to a wide variety of cationized cellulose nanocrystals through a simple one-pot reaction. In this study, cationic CNCs were prepared through the use of 4-(1-bromoethyl)benzoic acid or 4-bromomethylbenzoic acid, p-toluenesulfonyl chloride, CNCs, and two different amines, 1-methylimidazole and 4-dimethylaminopyridine. The amines acted as both the base catalyst for the esterification and the nucleophile to form the cationic charge. This method offers a versatile and straightforward route to prepare a variety of different cationic nanocrystals and therefore tailor their interaction with their environment.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Advanced Cellulose Research Studies · Polysaccharides and Plant Cell Walls · Lignin and Wood Chemistry
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (28)
Show source-provided references
1. Beamson G, Briggs D (eds) (2000) XPS of polymers database. SurfaceSpectra, Manchester
2. Beck-Candanedo S, Roman M, Gray DG (2005) Effect of reaction conditions on the properties and behavior of wood cellulose nanocrystal suspensions. Biomacromolecules 6:1048–105410.1021/bm049300p ↗
3. Caporali S, Bardi U, Lavacchi A (2006) X-ray photoelectron spectroscopy and low energy ion scattering studies on 1-buthyl-3-methyl-imidazolium bis(trifluoromethane) sulfonimide. J Electron Spectrosc Relat Phenom 151:4–810.1016/j.elspec.2005.09.010 ↗
4. de la Motte H, Hasani M, Brelid H, Westman G (2011) Molecular characterization of hydrolyzed cationized nanocrystalline cellulose, cotton cellulose and softwood kraft pulp using high resolution 1D and 2D NMR. Carbohydr Polym 85:738–74610.1016/j.carbpol.2011.03.038 ↗
5. Dufresne A (2012) Nanocellulose, from nature to high performance tailored materials. De Gruyter, Berlin10.1515/9783110254600 ↗
6. Eichhorn SJ, Dufresne A, Aranguren M, Marcovich NE, Capadona JR, Rowan SJ, Weder C, Thielemans W, Roman M, Renneckar S, Gindl W, Veigel S, Keckes J, Yano H, Abe K, Nogi M, Nakagaito AN, Mangalam A, Simonsen J, Benight AS, Bismarck A, Berglund LA, Peijs T (2010) Review: current international research into cellulose nanofibres and nanocomposites. J Mater Sci 45:1–3310.1007/s10853-009-3874-0 ↗
7. Elazzouzi-Hafraoui S, Nishiyama Y, Putaux J, Heux L, Dubreuil F, Rochas C (2008) The shape and size distribution of crystalline nanoparticles prepared by acid hydrolysis of native cellulose. Biomacromolecules 9:57–6510.1021/bm700769p ↗
8. Eyley S, Thielemans W (2011) Imidazolium grafted cellulose nanocrystals for ion exchange applications. Chem Commun 47:4177–417910.1039/c0cc05359g ↗
9. Goussé C, Chanzy H, Excoffier G, Soubeyrand L, Fleury E (2002) Stable suspensions of partially silylated cellulose whiskers dispersed in organic solvents. Polymer 43:2645–265110.1016/S0032-3861(02)00051-4 ↗
10. Habibi Y, Chanzy H, Vignon MR (2006) Tempo-mediated surface oxidation of cellulose whiskers. Cellulose 13:679–68710.1007/s10570-006-9075-y ↗
11. Habibi Y, Lucia LA, Rojas OJ (2010) Cellulose nanocrystals: chemistry, self-assembly and applications. Chem Rev 110:3479–350010.1021/cr900339w ↗
12. Hasani M, Cranston ED, Westman G, Gray DG (2008) Cationic surface functionalization of cellulose nanocrystals. Soft Matter 4:2238–224410.1039/B806789A ↗
13. Heux L, Chauve G, Bonini C (2000) Nonflocculating and chiral-nematic self-ordering of cellulose microcrystals suspensions in nonpolar solvents. Langmuir 16:8210–821210.1021/la9913957 ↗
14. Jasmani L, Eyley S, Wallbridge R, Thielemans W (2013) A facile one-pot route to cationic cellulose nanocrystals. Nanoscale 5:10,207–10,21110.1039/c3nr03456a ↗
15. Klemm D, Kramer F, Moritz S, Lindström T, Ankerfors M, Gray D, Dorris A (2011) New materials from nature. Angew Chem Int Ed 50:5438–546610.1002/anie.201001273 ↗
16. Kolbeck C, Cremer T, Lovelock KRJ, Paape N, Schulz PS, Wasserscheid P, Maier F, Steinrück HP (2009) Influence of different anions on the surface composition of ionic liquids studied using arxps. J Phys Chem B 113:8682–868810.1021/jp902978r ↗
17. Labet M, Thielemans W (2011) Improving the reproducibility of chemical reactions on the surface of cotton nanocrystals: rop of caprolactone as a case study. Cellulose 18:607–61710.1007/s10570-011-9527-x ↗
18. Lovelock KRJ, Villar-Garcia IJ, Maier F, Steinrück HP, Licence P (2010) Photoelectron spectroscopy of ionic liquid-based interfaces. Chem Rev 110:5158–519010.1021/cr100114t ↗
19. Montanari S, Roumani M, Heux L, Vignon MR (2005) Topochemistry of carboxylated cellulose nanocrystals resulting from tempo-mediated oxidation. Macromolecules 38:1665–167110.1021/ma048396c ↗
20. Morandi G, Heath L, Thielemans W (2009) Cellulose nanocrystals grafted with polystyrene chains through surface-initiated atom transfer radical polymerization. Langmuir 25:8280–828610.1021/la900452a ↗
21. Nishiyama Y, Langan P, Chanzy H (2002) Crystal structure and hydrogen-bonding system in cellulose I $$\beta$$ β from synchrotron X-ray and neutron fiber diffraction. J Am Chem Soc 124:9074–908210.1021/ja0257319 ↗
22. Song Y, Sun Y, Zhang X, Zhou J, Zhang L (2008) Homogeneous quaternization of cellulose in NaOH/urea aqueous solutions as gene carriers. Biomacromolecules 9:2259–226410.1021/bm800429a ↗
23. Song Y, Zhou J, Li Q, Guo Y, Zhang L (2009) Preparation and characterization of novel quaternized cellulose nanoparticles as protein carriers. Macromol Biosci 9:857–86310.1002/mabi.200800371 ↗
24. Thygesen A, Oddershede J, Lilholt H, Thomsen AB, Ståhl K (2005) On the determination of crystallinity and cellulose content in plant fibres. Cellulose 12:563–57610.1007/s10570-005-9001-8 ↗
25. Vandamme D, Eyley S, Van den Mooter G, Muylaert K, Thielemans W (2015) Highly charged cellulose-based nanocrystals as flocculants for harvesting chlorella vulgaris. Bioresour Technol. doi: 10.1016/j.biortech.2015.07.03910.1016/j.biortech.2015.07.039 ↗
26. Yuan H, Nishiyama Y, Wada M, Kuga S (2006) Surface acylation of cellulose whiskers by drying aqueous emulsion. Biomacromolecules 7:696–70010.1021/bm050828j ↗
27. Zaman M, Xiao H, Chibante F, Ni Y (2012) Synthesis and characterization of cationically modified nanocrystalline cellulose. Carbohydr Polym 89:163–17010.1016/j.carbpol.2012.02.066 ↗
28. Zoppe JO, Habibi Y, Rojas OJ, Venditti RA, Johansson LS, Efimenko K, Österberg M, Laine J (2010) Poly(n-isopropylacrylamide) brushes grafted from cellulose nanocrystals via surface-initiated single-electron transfer living radical polymerization. Biomacromolecules 11:2683–269110.1021/bm100719d ↗