Amino-modified cellulose nanocrystals with adjustable hydrophobicity from combined regioselective oxidation and reductive amination

Carbohydrate Polymers

Volumn 136, Issue , 2016, Pages 581-587

  Sirviö, Juho Antti ^a   Visanko, Miikka ^a   Laitinen, Ossi ^a   Ämmälä, Ari ^a   Liimatainen, Henrikki ^a  

^a UNIVERSITY OF OULU   (Finland)

Author keywords

Cellulose nanocrystalsa; Hydrophobicity; Modifiable properties; Periodate oxidation; Reductive amination

Indexed keywords

AMINATION; AMINES; CELLULOSE; CELLULOSE DERIVATIVES; CHAIN LENGTH; CHAINS; DISPERSIONS; NANOCRYSTALS; OXIDATION; POLYELECTROLYTES; REGIOSELECTIVITY;

AMPHIPHILIC POLYELECTROLYTES; CELLULOSE NANOCRYSTAL (CNCS); HIGH PRESSURE HOMOGENIZER; MODIFIABLE PROPERTIES; PERIODATE OXIDATION; POTENTIAL TECHNIQUES; REDUCTIVE AMINATION; REGIOSELECTIVE OXIDATION;

HYDROPHOBICITY;

AMINATION; CELLULOSE DERIVATIVES; OXIDATION; WATER REPELLENCE;

AMINE; CELLULOSE; NANOPARTICLE; SURFACTANT;

ANALOGS AND DERIVATIVES; CHEMICAL PHENOMENA; CHEMISTRY; OXIDATION REDUCTION REACTION;

AMINES; CELLULOSE; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; NANOPARTICLES; OXIDATION-REDUCTION; SURFACE-ACTIVE AGENTS;

EID: 84943374511     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2015.09.089     Document Type: Article

References (38)

1. A.F. Bettencourt, C.B. Neves, M.S. de Almeida, L.M. Pinheiro, S.A. e Oliveira, L.P. Lopes, and et al. Biodegradation of acrylic based resins: A review Dental Materials 26 5 2010 e171 e180 10.1016/j.dental.2010.01.006
2. W.-P. Cheng, C. Thompson, S.M. Ryan, T. Aguirre, L. Tetley, and D.J. Brayden In vitro and in vivo characterisation of a novel peptide delivery system: Amphiphilic polyelectrolyte-salmon calcitonin nanocomplexes Journal of Controlled Release 147 2 2010 289 297 10.1016/j.jconrel.2010.07.128
3. E.M. Dangerfield, S.A. Gulab, C.H. Plunkett, M.S.M. Timmer, and B.L. Stocker A fast, efficient and stereoselective synthesis of hydroxy-pyrrolidines Carbohydrate Research 345 10 2010 1360 1365 10.1016/j.carres.2010.03.016
4. J. Galindo-Alvarez, K.-A. Le, V. Sadtler, P. Marchal, P. Perrin, C. Tribet, and et al. Enhanced stability of nanoemulsions using mixtures of non-ionic surfactant and amphiphilic polyelectrolyte Colloids and Surfaces A: Physicochemical and Engineering Aspects 389 1-3 2011 237 245 10.1016/j.colsurfa.2011.08.021
5. S. Genest, S. Schwarz, K. Petzold-Welcke, T. Heinze, and B. Voit Characterization of highly substituted, cationic amphiphilic starch derivatives: Dynamic surface tension and intrinsic viscosity Starch 65 11-12 2013 999 1010 10.1002/star.201200295
6. L. Ghimici, and M. Nichifor Novel biodegradable flocculanting agents based on cationic amphiphilic polysaccharides Bioresource Technology 101 22 2010 8549 8554 10.1016/j.biortech.2010.06.049
7. L. Ghimici, and M. Nichifor Flocculation by cationic amphiphilic polyelectrolyte: Relating efficiency with the association of polyelectrolyte in the initial solution Colloids and Surfaces A: Physicochemical and Engineering Aspects 415 2012 142 147 10.1016/j.colsurfa.2012.09.016
8. A. Guyomard, E. Dé, T. Jouenne, J.-J. Malandain, G. Muller, and K. Glinel Incorporation of a hydrophobic antibacterial peptide into amphiphilic polyelectrolyte multilayers: A bioinspired approach to prepare biocidal thin coatings Advanced Functional Materials 18 5 2008 758 765 10.1002/adfm.200700793
9. M. Henriksson, G. Henriksson, L.A. Berglund, and T. Lindström An environmentally friendly method for enzyme-assisted preparation of microfibrillated cellulose (MFC) nanofibers European Polymer Journal 43 8 2007 3434 3441 10.1016/j.eurpolymj.2007.05.038
10. S. Hokkanen, E. Repo, and M. Sillanpää Removal of heavy metals from aqueous solutions by succinic anhydride modified mercerized nanocellulose Chemical Engineering Journal 223 2013 40 47 10.1016/j.cej.2013.02.054
11. P. Huang, W. Wang, J. Zhou, F. Zhao, Y. Zhang, J. Liu, and et al. Amphiphilic polyelectrolyte/prodrug nanoparticles constructed by synergetic electrostatic and hydrophobic interactions with cooperative pH-sensitivity for controlled doxorubicin delivery ACS Applied Materials & Interfaces 7 11 2015 6340 6350 10.1021/acsami.5b00962
12. D. Jańczewski, N. Tomczak, M.-Y. Han, and G.J. Vancso Synthesis of functionalized amphiphilic polymers for coating quantum dots Nature Protocols 6 10 2011 1546 1553 10.1038/nprot.2011.381
13. F. Jiang, and Y.-L. Hsieh Amphiphilic superabsorbent cellulose nanofibril aerogels Journal of Materials Chemistry A 2 18 2014 6337 6342 10.1039/C4TA00743C
14. L. Jin, Y. Wei, Q. Xu, W. Yao, and Z. Cheng Cellulose nanofibers prepared from TEMPO-oxidation of kraft pulp and its flocculation effect on kaolin clay Journal of Applied Polymer Science 131 12 2014 10.1002/app.40450
15. U.-J. Kim, S. Kuga, M. Wada, T. Okano, and T. Kondo Periodate oxidation of crystalline cellulose Biomacromolecules 1 3 2000 488 492 10.1021/bm0000337
16. D. Klemm, F. Kramer, S. Moritz, T. Lindström, M. Ankerfors, D. Gray, and et al. Nanocelluloses: A new family of nature-based materials Angewandte Chemie International Edition 50 24 2011 5438 5466 10.1002/anie.201001273
17. A. Lafuma, and D. Quéré Superhydrophobic states Nature Materials 2 7 2003 457 460 10.1038/nmat924
18. O. Laitinen, K. Kemppainen, A. Ämmälä, J.A. Sirviö, H. Liimatainen, and J. Niinimäki Use of chemically modified nanocelluloses in flotation of hematite and quartz Industrial & Engineering Chemistry Research 53 52 2014 20092 20098 10.1021/ie503415t
19. W.-M. Li, D.-M. Liu, and S.-Y. Chen Amphiphilically-modified gelatin nanoparticles: Self-assembly behavior, controlled biodegradability, and rapid cellular uptake for intracellular drug delivery Journal of Materials Chemistry 21 33 2011 12381 12388 10.1039/C1JM10188A
20. Y. Li, H. Zhu, F. Shen, J. Wan, S. Lacey, Z. Fang, and et al. Nanocellulose as green dispersant for two-dimensional energy materials Nano Energy 13 2015 346 354 10.1016/j.nanoen.2015.02.015
21. H. Liimatainen, J. Sirviö, A. Haapala, O. Hormi, and J. Niinimäki Characterization of highly accessible cellulose microfibers generated by wet stirred media milling Carbohydrate Polymers 83 4 2011 2005 2010 10.1016/j.carbpol.2010.11.007
22. H. Liimatainen, J. Sirviö, H. Pajari, O. Hormi, and J. Niinimäki Regeneration and recycling of aqueous periodate solution in dialdehyde cellulose production Journal of Wood Chemistry and Technology 33 4 2013 258 266 10.1080/02773813.2013.783076
23. H. Liimatainen, T. Suopajärvi, J. Sirviö, O. Hormi, and J. Niinimäki Fabrication of cationic cellulosic nanofibrils through aqueous quaternization pretreatment and their use in colloid aggregation Carbohydrate Polymers 103 2014 187 192 10.1016/j.carbpol.2013.12.042
24. H.J. Lim, E.C. Cho, J. Shim, D.-H. Kim, E.J. An, and J. Kim Polymer-associated liposomes as a novel delivery system for cyclodextrin-bound drugs Journal of Colloid and Interface Science 320 2 2008 460 468 10.1016/j.jcis.2008.01.025
25. C.-A.J. Lin, R.A. Sperling, J.K. Li, T.-Y. Yang, P.-Y. Li, M. Zanella, and et al. Design of an amphiphilic polymer for nanoparticle coating and functionalization Small 4 3 2008 334 341 10.1002/smll.200700654
26. 3+ from industrial effluents Journal of Hazardous Materials 294 2015 177 185 10.1016/j.jhazmat.2015.04.001
27. +) from water via surface adsorption Cellulose 21 1 2013 449 461 10.1007/s10570-013-0139-5
28. R. Nakao, H. Rhee, and Y. Uozumi Hydrogenation and dehalogenation under aqueous conditions with an amphiphilic-polymer-supported nanopalladium catalyst Organic Letters 7 1 2005 163 165 10.1021/ol047670k
29. T. Saito, S. Kimura, Y. Nishiyama, and A. Isogai Cellulose nanofibers prepared by TEMPO-mediated oxidation of native cellulose Biomacromolecules 8 8 2007 2485 2491 10.1021/bm0703970
30. S. Schwarz, W. Jaeger, B.-R. Paulke, S. Bratskaya, N. Smolka, and J. Bohrisch Cationic flocculants carrying hydrophobic functionalities: Applications for solid/liquid separation Journal of Physical Chemistry B 111 29 2007 8649 8654 10.1021/jp070358i
31. J.A. Sirviö, H. Liimatainen, J. Niinimäki, and O. Hormi Sustainable packaging materials based on wood cellulose RSC Advances 3 37 2013 16590 10.1039/c3ra43264e
32. J.A. Sirviö, M. Visanko, and H. Liimatainen Deep eutectic solvent system based on choline chloride-urea as a pre-treatment for nanofibrillation of wood cellulose Green Chemistry 17 6 2015 3401 3406 10.1039/C5GC00398A
33. J. Sirvio, U. Hyvakko, H. Liimatainen, J. Niinimaki, and O. Hormi Periodate oxidation of cellulose at elevated temperatures using metal salts as cellulose activators Carbohydrate Polymers 83 3 2011 1293 1297 10.1016/j.carbpol.2010.09.036
34. B.C. Smith Infrared spectral interpretation: A systematic approach 1998 CRC Press
35. T. Suopajärvi, E. Koivuranta, H. Liimatainen, and J. Niinimäki Flocculation of municipal wastewaters with anionic nanocelluloses: Influence of nanocellulose characteristics on floc morphology and strength Journal of Environmental Chemical Engineering 2 4 2014 2005 2012 10.1016/j.jece.2014.08.023
36. T. Suopajärvi, H. Liimatainen, O. Hormi, and J. Niinimäki Coagulation-flocculation treatment of municipal wastewater based on anionized nanocelluloses Chemical Engineering Journal 231 2013 59 67 10.1016/j.cej.2013.07.010
37. M. Visanko, H. Liimatainen, J.A. Sirviö, J.P. Heiskanen, J. Niinimäki, and O. Hormi Amphiphilic cellulose nanocrystals from acid-free oxidative treatment: Physicochemical characteristics and use as an oil-water stabilizer Biomacromolecules 15 7 2014 2769 2775 10.1021/bm500628g
38. M. Visanko, H. Liimatainen, J.A. Sirviö, K.S. Mikkonen, M. Tenkanen, R. Sliz, and et al. Butylamino-functionalized cellulose nanocrystal films: Barrier properties and mechanical strength RSC Advances 5 20 2015 15140 15146 10.1039/C4RA15445B