One-Pot Water-Based Hydrophobic Surface Modification of Cellulose Nanocrystals Using Plant Polyphenols

ACS Sustainable Chemistry and Engineering

Volumn 5, Issue 6, 2017, Pages 5018-5026

  Hu, Zhen ^a   Berry, Richard M ^b   Pelton, Robert ^a   Cranston, Emily D ^a  

^a MCMASTER UNIVERSITY   (Canada)

^b INSTITUTE FOR RESEARCH IN IMMUNOLOGY AND CANCER   (Canada)

Author keywords

cellulose nanocrystals; dispersion; hydrophobicity; plant polyphenols; surface modification; tannic acid

Indexed keywords

CELLULOSE; CELLULOSE DERIVATIVES; DISPERSION (WAVES); FLAVONOIDS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; HYDROPHOBICITY; LIGHT SCATTERING; LIQUID CRYSTALS; NANOCRYSTALS; ORGANIC SOLVENTS; SELF ASSEMBLY; SURFACE CHEMISTRY; SURFACE TREATMENT; SUSPENSIONS (FLUIDS); TANNINS; X RAY DIFFRACTION;

CELLULOSE NANO-CRYSTALS; CELLULOSE NANOCRYSTAL (CNCS); PARTICLE HYDROPHOBICITY; PLANT POLYPHENOLS; RHEOLOGICAL MODIFIERS; SELF-ASSEMBLY BEHAVIORS; TANNIC ACID; TURBIDITY MEASUREMENTS;

X RAY PHOTOELECTRON SPECTROSCOPY;

CELLULOSE DERIVATIVES; LIQUID CRYSTALS; POLYPHENOLS; SOLVENTS; SURFACE TREATMENT; WATER REPELLENCE;

EID: 85020237001     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/acssuschemeng.7b00415     Document Type: Article

References (57)

1. Habibi, Y.; Lucia, L. A.; Rojas, O. J. Cellulose Nanocrystals: Chemistry, Self-Assembly, and Applications Chem. Rev. 2010, 110, 3479-3500 10.1021/cr900339w
2. Eichhorn, S. J. Cellulose Nanowhiskers: Promising Materials for Advanced Applications Soft Matter 2011, 7, 303-315 10.1039/C0SM00142B
3. Moon, R. J.; Martini, A.; Nairn, J.; Simonsen, J.; Youngblood, J. Cellulose Nanomaterials Review: Structure, Properties and Nanocomposites Chem. Soc. Rev. 2011, 40, 3941-3994 10.1039/c0cs00108b
4. Mariano, M.; El Kissi, N.; Dufresne, A. Cellulose Nanocrystals and Related Nanocomposites: Review of Some Properties and Challenges J. Polym. Sci., Part B: Polym. Phys. 2014, 52, 791-806 10.1002/polb.23490
5. Habibi, Y. Key Advances in the Chemical Modification of Nanocelluloses Chem. Soc. Rev. 2014, 43, 1519-1542 10.1039/C3CS60204D
6. Eyley, S.; Thielemans, W. Surface Modification of Cellulose Nanocrystals Nanoscale 2014, 6, 7764-7779 10.1039/C4NR01756K
7. Salajková, M.; Berglund, L. A.; Zhou, Q. Hydrophobic Cellulose Nanocrystals Modified with Quaternary Ammonium Salts J. Mater. Chem. 2012, 22, 19798-19805 10.1039/c2jm34355j
8. Shimizu, M.; Saito, T.; Fukuzumi, H.; Isogai, A. Hydrophobic, Ductile, and Transparent Nanocellulose Films with Quaternary Alkylammonium Carboxylates on Nanofibril Surfaces Biomacromolecules 2014, 15, 4320-4325 10.1021/bm501329v
9. Shimizu, M.; Saito, T.; Isogai, A. Bulky Quaternary Alkylammonium Counterions Enhance the Nanodispersibility of 2,2,6,6-Tetramethylpiperidine-1-Oxyl-Oxidized Cellulose in Diverse Solvents Biomacromolecules 2014, 15, 1904-1909 10.1021/bm500384d
10. Ansari, F.; Salajková, M.; Zhou, Q.; Berglund, L. A. Strong Surface Treatment Effects on Reinforcement Efficiency in Biocomposites Based on Cellulose Nanocrystals in Poly(Vinyl Acetate) Matrix Biomacromolecules 2015, 16, 3916-3924 10.1021/acs.biomac.5b01245
11. Abitbol, T.; Marway, H. S.; Cranston, E. D. Surface Modification of Cellulose Nanocrystals with Cetyltrimethylammonium Bromide Nord. Pulp Pap. Res. J. 2014, 29, 46-57 10.3183/NPPRJ-2014-29-01-p046-057
12. Abraham, E.; Nevo, Y.; Slattegard, R.; Attias, N.; Sharon, S.; Lapidot, S.; Shoseyov, O. Highly Hydrophobic Thermally Stable Liquid Crystalline Cellulosic Nanomaterials ACS Sustainable Chem. Eng. 2016, 4, 1338-1346 10.1021/acssuschemeng.5b01363
13. Girouard, N. M.; Xu, S.; Schueneman, G. T.; Shofner, M. L.; Meredith, J. C. Site-Selective Modification of Cellulose Nanocrystals with Isophorone Diisocyanate and Formation of Polyurethane-Cnc Composites ACS Appl. Mater. Interfaces 2016, 8, 1458-1467 10.1021/acsami.5b10723
14. Shang, W.; Huang, J.; Luo, H.; Chang, P. R.; Feng, J.; Xie, G. Hydrophobic Modification of Cellulose Nanocrystal Via Covalently Grafting of Castor Oil Cellulose 2013, 20, 179-190 10.1007/s10570-012-9795-0
15. Cao, X.; Habibi, Y.; Lucia, L. A. One-Pot Polymerization, Surface Grafting, and Processing of Waterborne Polyurethane-Cellulose Nanocrystal Nanocomposites J. Mater. Chem. 2009, 19, 7137-7145 10.1039/b910517d
16. Fumagalli, M.; Ouhab, D.; Boisseau, S. M.; Heux, L. Versatile Gas-Phase Reactions for Surface to Bulk Esterification of Cellulose Microfibrils Aerogels Biomacromolecules 2013, 14, 3246-3255 10.1021/bm400864z
17. Fumagalli, M.; Sanchez, F.; Boisseau, S. M.; Heux, L. Gas-Phase Esterification of Cellulose Nanocrystal Aerogels for Colloidal Dispersion in Apolar Solvents Soft Matter 2013, 9, 11309-11317 10.1039/c3sm52062e
18. Dash, R.; Elder, T.; Ragauskas, A. J. Grafting of Model Primary Amine Compounds to Cellulose Nanowhiskers through Periodate Oxidation Cellulose 2012, 19, 2069-2079 10.1007/s10570-012-9769-2
19. Lin, N.; Huang, J.; Chang, P. R.; Feng, J.; Yu, J. Surface Acetylation of Cellulose Nanocrystal and Its Reinforcing Function in Poly(Lactic Acid) Carbohydr. Polym. 2011, 83, 1834-1842 10.1016/j.carbpol.2010.10.047
20. de Oliveira Taipina, M.; Ferrarezi, M. M. F.; Yoshida, I. V. P.; Gonçalves, d. M. C. Surface Modification of Cotton Nanocrystals with a Silane Agent Cellulose 2013, 20, 217-226 10.1007/s10570-012-9820-3
21. Ljungberg, N.; Bonini, C.; Bortolussi, F.; Boisson, C.; Heux, L. Cavaillé. New Nanocomposite Materials Reinforced with Cellulose Whiskers in Atactic Polypropylene: Effect of Surface and Dispersion Characteristics Biomacromolecules 2005, 6, 2732-2739 10.1021/bm050222v
22. Harrisson, S.; Drisko, G. L.; Malmström, E.; Hult, A.; Wooley, K. L. Hybrid Rigid/Soft and Biologic/Synthetic Materials: Polymers Grafted onto Cellulose Microcrystals Biomacromolecules 2011, 12, 1214-1223 10.1021/bm101506j
23. Pei, A.; Malho, J.-M.; Ruokolainen, J.; Zhou, Q.; Berglund, L. A. Strong Nanocomposite Reinforcement Effects in Polyurethane Elastomer with Low Volume Fraction of Cellulose Nanocrystals Macromolecules 2011, 44, 4422-4427 10.1021/ma200318k
24. Rosilo, H.; Kontturi, E.; Seitsonen, J.; Kolehmainen, E.; Ikkala, O. Transition to Reinforced State by Percolating Domains of Intercalated Brush-Modified Cellulose Nanocrystals and Poly(Butadiene) in Cross-Linked Composites Based on Thiol-Ene Click Chemistry Biomacromolecules 2013, 14, 1547-1554 10.1021/bm400185z
25. Labet, M.; Thielemans, W.; Dufresne, A. Polymer Grafting onto Starch Nanocrystals Biomacromolecules 2007, 8, 2916-2927 10.1021/bm700468f
26. Habibi, Y.; Goffin, A.-L.; Schiltz, N.; Duquesne, E.; Dubois, P.; Dufresne, A. Bionanocomposites Based on Poly(E-Caprolactone)-Grafted Cellulose Nanocrystals by Ring-Opening Polymerization J. Mater. Chem. 2008, 18, 5002-5010 10.1039/b809212e
27. Peltzer, M.; Pei, A.; Zhou, Q.; Berglund, L.; Jiménez, A. Surface Modification of Cellulose Nanocrystals by Grafting with Poly(Lactic Acid) Polym. Int. 2014, 63, 1056-1062 10.1002/pi.4610
28. Tian, C.; Fu, S.; Habibi, Y.; Lucia, L. A. Polymerization Topochemistry of Cellulose Nanocrystals: A Function of Surface Dehydration Control Langmuir 2014, 30, 14670-14679 10.1021/la503990u
29. Goffin, A.-L.; Raquez, J.-M.; Duquesne, E.; Siqueira, G.; Habibi, Y.; Dufresne, A.; Dubois, P. From Interfacial Ring-Opening Polymerization to Melt Processing of Cellulose Nanowhisker-Filled Polylactide-Based Nanocomposites Biomacromolecules 2011, 12, 2456-2465 10.1021/bm200581h
30. Morandi, G.; Heath, L.; Thielemans, W. Cellulose Nanocrystals Grafted with Polystyrene Chains through Surface-Initiated Atom Transfer Radical Polymerization (Si-Atrp) Langmuir 2009, 25, 8280-8286 10.1021/la900452a
31. Li, S.; Xiao, M.; Zheng, A.; Xiao, H. Cellulose Microfibrils Grafted with Pba Via Surface-Initiated Atom Transfer Radical Polymerization for Biocomposite Reinforcement Biomacromolecules 2011, 12, 3305-3312 10.1021/bm200797a
32. Boujemaoui, A.; Mongkhontreerat, S.; Malmström, E.; Carlmark, A. Preparation and Characterization of Functionalized Cellulose Nanocrystals Carbohydr. Polym. 2015, 115, 457-464 10.1016/j.carbpol.2014.08.110
33. Yin, Y.; Tian, X.; Jiang, X.; Wang, H.; Gao, W. Modification of Cellulose Nanocrystal Via Si-Atrp of Styrene and the Mechanism of Its Reinforcement of Polymethylmethacrylate Carbohydr. Polym. 2016, 142, 206-212 10.1016/j.carbpol.2016.01.014
34. Wang, H.-D.; Roeder, R. D.; Whitney, R. A.; Champagne, P.; Cunningham, M. F. Graft Modification of Crystalline Nanocellulose by Cu(0)-Mediated Set Living Radical Polymerization J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 2800-2808 10.1002/pola.27754
35. Kan, K. H. M.; Li, J.; Wijesekera, K.; Cranston, E. D. Polymer-Grafted Cellulose Nanocrystals as pH-Responsive Reversible Flocculants Biomacromolecules 2013, 14, 3130-3139 10.1021/bm400752k
36. Kedzior, S. A.; Graham, L.; Moorlag, C.; Dooley, B. M.; Cranston, E. D. Poly(Methyl Methacrylate)-Grafted Cellulose Nanocrystals: One-Step Synthesis, Nanocomposite Preparation, and Characterization Can. J. Chem. Eng. 2016, 94, 811-822 10.1002/cjce.22456
37. Yoo, Y.; Youngblood, J. P. Green One-Pot Synthesis of Surface Hydrophobized Cellulose Nanocrystals in Aqueous Medium ACS Sustainable Chem. Eng. 2016, 4, 3927-3938 10.1021/acssuschemeng.6b00781
38. Lee, H.; Dellatore, S. M.; Miller, W. M.; Messersmith, P. B. Mussel-Inspired Surface Chemistry for Multifunctional Coatings Science 2007, 318, 426-430 10.1126/science.1147241
39. Sileika, T. S.; Barrett, D. G.; Zhang, R.; Lau, K. H. A.; Messersmith, P. B. Colorless Multifunctional Coatings Inspired by Polyphenols Found in Tea, Chocolate, and Wine Angew. Chem., Int. Ed. 2013, 52, 10766-10770 10.1002/anie.201304922
40. Ejima, H.; Richardson, J. J.; Liang, K.; Best, J. P.; van Koeverden, M. P.; Such, G. K.; Cui, J.; Caruso, F. One-Step Assembly of Coordination Complexes for Versatile Film and Particle Engineering Science 2013, 341, 154-157 10.1126/science.1237265
41. Hu, Z.; Marway, H. S.; Kasem, H.; Pelton, R.; Cranston, E. D. Dried and Redispersible Cellulose Nanocrystal Pickering Emulsions ACS Macro Lett. 2016, 5, 185-189 10.1021/acsmacrolett.5b00919
42. Hu, Z.; Cranston, E. Surface Modification of Cellulose Nanocrystals. U.S. Patent 20150368367, 2015.
43. Reid, M. S.; Villalobos, M.; Cranston, E. D. Benchmarking Cellulose Nanocrystals: From the Laboratory to Industrial Production Langmuir 2017, 33, 1583 10.1021/acs.langmuir.6b03765
44. Beck, S.; Bouchard, J.; Berry, R. Dispersibility in Water of Dried Nanocrystalline Cellulose Biomacromolecules 2012, 13, 1486-1494 10.1021/bm300191k
45. Tang, H. R.; Covington, A. D.; Hancock, R. A. Structure-Activity Relationships in the Hydrophobic Interactions of Polyphenols with Cellulose and Collagen Biopolymers 2003, 70, 403-413 10.1002/bip.10499
46. Hu, Z.; Cranston, E. D.; Ng, R.; Pelton, R. Tuning Cellulose Nanocrystal Gelation with Polysaccharides and Surfactants Langmuir 2014, 30, 2684-2692 10.1021/la404977t
47. Kim, S.; Gim, T.; Kang, S. M. Versatile, Tannic Acid-Mediated Surface Pegylation for Marine Antifouling Applications ACS Appl. Mater. Interfaces 2015, 7, 6412-6416 10.1021/acsami.5b01304
48. Wang, Z.; Xu, Y.; Liu, Y.; Shao, L. A Novel Mussel-Inspired Strategy toward Superhydrophobic Surfaces for Self-Driven Crude Oil Spill Cleanup J. Mater. Chem. A 2015, 3, 12171-12178 10.1039/C5TA01767J
49. Chen, S.; Li, X.; Yang, Z.; Zhou, S.; Luo, R.; Maitz, M. F.; Zhao, Y.; Wang, J.; Xiong, K.; Huang, N. A Simple One-Step Modification of Various Materials for Introducing Effective Multi-Functional Groups Colloids Surf., B 2014, 113, 125-133 10.1016/j.colsurfb.2013.08.041
50. Johansson, L.-S.; Campbell, J. M. Reproducible Xps on Biopolymers: Cellulose Studies Surf. Interface Anal. 2004, 36, 1018-1022 10.1002/sia.1827
51. Liebscher, J.; Mrówczyński, R.; Scheidt, H. A.; Filip, C.; Hǎdade, N. D.; Turcu, R.; Bende, A.; Beck, S. Structure of Polydopamine: A Never-Ending Story? Langmuir 2013, 29, 10539-10548 10.1021/la4020288
52. Lopez-Martinez, L. M.; Santacruz-Ortega, H.; Navarro, R. E.; Sotelo-Mundo, R. R.; Gonzalez-Aguilar, G. A. A H-1 Nmr Investigation of the Interaction between Phenolic Acids Found in Mango (Manguifera Indica Cv Ataulfo) and Papaya (Carica Papaya Cv Maradol) and 1,1-Diphenyl-2-Picrylhydrazyl (Dpph) Free Radicals PLoS One 2015, 10, e0140242 10.1371/journal.pone.0140242
53. Ariga, K. Manipulation of Nanoscale Materials: An Introduction to Nanoarchitectonics; RSC Publications: Cambridge, U.K., 2012.
54. Spinella, S.; Maiorana, A.; Qian, Q.; Dawson, N. J.; Hepworth, V.; McCallum, S. A.; Ganesh, M.; Singer, K. D.; Gross, R. A. Concurrent Cellulose Hydrolysis and Esterification to Prepare a Surface-Modified Cellulose Nanocrystal Decorated with Carboxylic Acid Moieties ACS Sustainable Chem. Eng. 2016, 4, 1538-1550 10.1021/acssuschemeng.5b01489
55. Huang, Y.; He, M.; Lu, A.; Zhou, W.; Stoyanov, S. D.; Pelan, E. G.; Zhang, L. Hydrophobic Modification of Chitin Whisker and Its Potential Application in Structuring Oil Langmuir 2015, 31, 1641-1648 10.1021/la504576p
56. Pan, L.; Wang, H.; Wu, C.; Liao, C.; Li, L. Tannic-Acid-Coated Polypropylene Membrane as a Separator for Lithium-Ion Batteries ACS Appl. Mater. Interfaces 2015, 7, 16003-16010 10.1021/acsami.5b04245
57. Dankovich, T. A.; Gray, D. G. Contact Angle Measurements on Smooth Nanocrystalline Cellulose (I) Thin Films J. Adhes. Sci. Technol. 2011, 25, 699-708 10.1163/016942410X525885