Convenient Synthesis of Hybrid Polymer Materials by AGET-ATRP Polymerization of Pickering Emulsions Stabilized by Cellulose Nanocrystals Grafted with Reactive Moieties

Biomacromolecules

Volumn 20, Issue 1, 2019, Pages 490-501

  Werner, Arthur ^a   Schmitt, Véronique ^a   Sèbe, Gilles ^a   Héroguez, Valérie ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE COMPOUNDS; CELLULOSE; CELLULOSE DERIVATIVES; GRAFTING (CHEMICAL); HYDROPHILICITY; NANOCRYSTALS; POLYMERIZATION; STYRENE;

CELLULOSE NANO-CRYSTALS; CELLULOSE NANOCRYSTAL (CNCS); DOUBLE EMULSIONS; FUNCTIONALIZATIONS; HYBRID POLYMERS; HYDROPHILIC/HYDROPHOBIC; PICKERING EMULSIONS; POLYMERIZATION CONDITIONS;

HYBRID MATERIALS;

ASCORBIC ACID; BROMIDE; CELLULOSE; MONOMER; NANOCRYSTAL; POLYMER; STYRENE; BUTYRIC ACID DERIVATIVE; NANOPARTICLE; STYRENE DERIVATIVE; SURFACTANT;

ARTICLE; ATOM TRANSFER RADICAL POLYMERIZATION; DISPERSITY; FLUORESCENCE MICROSCOPY; FOURIER TRANSFORM INFRARED SPECTROSCOPY; HYDROPHILICITY; HYDROPHOBICITY; IMMOBILIZATION; MOLECULAR WEIGHT; NANOEMULSION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SCANNING ELECTRON MICROSCOPY; SYNTHESIS; CHEMICAL PHENOMENA; CHEMISTRY; EMULSION; POLYMERIZATION;

BROMINE COMPOUNDS; CELLULOSE DERIVATIVES; COPOLYMERIZATION; STYRENE; WATER; WETTABILITY;

BROMIDES; BUTYRATES; CELLULOSE; EMULSIONS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; NANOPARTICLES; POLYMERIZATION; STYRENES; SURFACE-ACTIVE AGENTS;

EID: 85058812797     PISSN: 15257797     EISSN: 15264602     Source Type: Journal    
DOI: 10.1021/acs.biomac.8b01482     Document Type: Article

References (44)

1. Foster, E. J.; Moon, R. J.; Agarwal, U. P.; Bortner, M. J.; Bras, J.; Camarero-Espinosa, S.; Chan, K. J.; Clift, M. J. D.; Cranston, E. D.; Eichhorn, S. J. et al. Current Characterization Methods for Cellulose Nanomaterials. Chem. Soc. Rev. 2018, 47 (8), 2609-2679, 10.1039/C6CS00895J
2. Habibi, Y.; Lucia, L. A.; Rojas, O. J. Cellulose Nanocrystals: Chemistry, Self-Assembly, and Applications. Chem. Rev. 2010, 110 (6), 3479-3500, 10.1021/cr900339w
3. Azizi Samir, M. A. S.; Alloin, F.; Dufresne, A. Review of Recent Research into Cellulosic Whiskers, Their Properties and Their Application in Nanocomposite Field. Biomacromolecules 2005, 6 (2), 612-626, 10.1021/bm0493685
4. Lin, N.; Dufresne, A. Surface Chemistry, Morphological Analysis and Properties of Cellulose Nanocrystals with Gradiented Sulfation Degrees. Nanoscale 2014, 6 (10), 5384-5393, 10.1039/C3NR06761K
5. Capron, I.; Cathala, B. Surfactant-Free High Internal Phase Emulsions Stabilized by Cellulose Nanocrystals. Biomacromolecules 2013, 14 (2), 291-296, 10.1021/bm301871k
6. Sèbe, G.; Ham-Pichavant, F.; Pecastaings, G. Dispersibility and Emulsion-Stabilizing Effect of Cellulose Nanowhiskers Esterified by Vinyl Acetate and Vinyl Cinnamate. Biomacromolecules 2013, 14 (8), 2937-2944, 10.1021/bm400854n
7. Werner, A.; Schmitt, V.; Sèbe, G.; Héroguez, V. Synthesis of Surfactant-Free Micro- and Nanolatexes from Pickering Emulsions Stabilized by Acetylated Cellulose Nanocrystals. Polym. Chem. 2017, 8 (39), 6064-6072, 10.1039/C7PY01203A
8. Miao, C.; Tayebi, M.; Hamad, W. Y. Investigation of the Formation Mechanisms in High Internal Phase Pickering Emulsions Stabilized by Cellulose Nanocrystals. Philos. Trans. R. Soc., A 2018, 376 (2112), 20170039, 10.1098/rsta.2017.0039
9. Binks, B. P. Particles as Surfactants-similarities and Differences. Curr. Opin. Colloid Interface Sci. 2002, 7 (1-2), 21-41, 10.1016/S1359-0294(02)00008-0
10. Zhai, X.; Lin, D.; Liu, D.; Yang, X. Emulsions Stabilized by Nanofibers from Bacterial Cellulose: New Potential Food-Grade Pickering Emulsions. Food Res. Int. 2018, 103, 12-20, 10.1016/j.foodres.2017.10.030
11. Hedjazi, S.; Razavi, S. H. A Comparison of Canthaxanthine Pickering Emulsions, Stabilized with Cellulose Nanocrystals of Different Origins. Int. J. Biol. Macromol. 2018, 106, 489-497, 10.1016/j.ijbiomac.2017.08.030
12. Kalashnikova, I.; Bizot, H.; Bertoncini, P.; Cathala, B.; Capron, I. Cellulosic Nanorods of Various Aspect Ratios for Oil in Water Pickering Emulsions. Soft Matter 2013, 9 (3), 952-959, 10.1039/C2SM26472B
13. Wen, C.; Yuan, Q.; Liang, H.; Vriesekoop, F. Preparation and Stabilization of D-Limonene Pickering Emulsions by Cellulose Nanocrystals. Carbohydr. Polym. 2014, 112, 695-700, 10.1016/j.carbpol.2014.06.051
14. Kasiri, N.; Fathi, M. Production of Cellulose Nanocrystals from Pistachio Shells and Their Application for Stabilizing Pickering Emulsions. Int. J. Biol. Macromol. 2018, 106, 1023-1031, 10.1016/j.ijbiomac.2017.08.112
15. 2 -Switchable Pickering Emulsifiers. Polym. Chem. 2018, 9 (28), 3864-3872, 10.1039/C8PY00417J
16. Saidane, D.; Perrin, E.; Cherhal, F.; Guellec, F.; Capron, I. Some Modification of Cellulose Nanocrystals for Functional Pickering Emulsions. Philos. Trans. R. Soc., A 2016, 374 (2072), 20150139, 10.1098/rsta.2015.0139
17. Hu, Z.; Ballinger, S.; Pelton, R.; Cranston, E. D. Surfactant-Enhanced Cellulose Nanocrystal Pickering Emulsions. J. Colloid Interface Sci. 2015, 439, 139-148, 10.1016/j.jcis.2014.10.034
18. Cunha, A. G.; Mougel, J.-B.; Cathala, B.; Berglund, L. A.; Capron, I. Preparation of Double Pickering Emulsions Stabilized by Chemically Tailored Nanocelluloses. Langmuir 2014, 30 (31), 9327-9335, 10.1021/la5017577
19. He, Y. Preparation of Polyaniline/Nano-ZnO Composites via a Novel Pickering Emulsion Route. Powder Technol. 2004, 147 (1-3), 59-63, 10.1016/j.powtec.2004.09.038
20. Liu, H.; Wang, C.; Gao, Q.; Chen, J.; Liu, X.; Tong, Z. One-Pot Fabrication of Magnetic Nanocomposite Microcapsules. Mater. Lett. 2009, 63 (11), 884-886, 10.1016/j.matlet.2009.01.034
21. Bon, S. A. F.; Colver, P. J. Pickering Miniemulsion Polymerization Using Laponite Clay as a Stabilizer. Langmuir 2007, 23 (16), 8316-8322, 10.1021/la701150q
22. Kedzior, S. A.; Marway, H. S.; Cranston, E. D. Tailoring Cellulose Nanocrystal and Surfactant Behavior in Miniemulsion Polymerization. Macromolecules 2017, 50 (7), 2645-2655, 10.1021/acs.macromol.7b00516
23. Werner, A.; Sèbe, G.; Héroguez, V. A New Strategy to Elaborate Polymer Composites via Pickering Emulsion Polymerization of a Wide Range of Monomers. Polym. Chem. 2018, 9, 5043-5050, 10.1039/C8PY01022F
24. Meng, T.; Gao, X.; Zhang, J.; Yuan, J.; Zhang, Y.; He, J. Graft Copolymers Prepared by Atom Transfer Radical Polymerization (ATRP) from Cellulose. Polymer 2009, 50 (2), 447-454, 10.1016/j.polymer.2008.11.011
25. Labet, M.; Thielemans, W. Improving the Reproducibility of Chemical Reactions on the Surface of Cellulose Nanocrystals: ROP of ϵ-Caprolactone as a Case Study. Cellulose 2011, 18 (3), 607-617, 10.1007/s10570-011-9527-x
26. Zoppe, J. O.; Venditti, R. A.; Rojas, O. J. Pickering Emulsions Stabilized by Cellulose Nanocrystals Grafted with Thermo-Responsive Polymer Brushes. J. Colloid Interface Sci. 2012, 369 (1), 202-209, 10.1016/j.jcis.2011.12.011
27. Tang, J.; Berry, R. M.; Tam, K. C. Stimuli-Responsive Cellulose Nanocrystals for Surfactant-Free Oil Harvesting. Biomacromolecules 2016, 17 (5), 1748-1756, 10.1021/acs.biomac.6b00144
28. Chen, T.; Colver, P. J.; Bon, S. A. F. Organic-Inorganic Hybrid Hollow Spheres Prepared from TiO 2-Stabilized Pickering Emulsion Polymerization. Adv. Mater. 2007, 19 (17), 2286-2289, 10.1002/adma.200602447
29. Wu, M.; Forero Ramirez, L. M.; Rodriguez Lozano, A.; Quémener, D.; Babin, J.; Durand, A.; Marie, E.; Six, J.-L.; Nouvel, C. First Multi-Reactive Dextran-Based Inisurf for Atom Transfer Radical Polymerization in Miniemulsion. Carbohydr. Polym. 2015, 130, 141-148, 10.1016/j.carbpol.2015.05.002
30. Chen, Y.; Wang, C.; Chen, J.; Liu, X.; Tong, Z. Growth of Lightly Crosslinked PHEMA Brushes and Capsule Formation Using Pickering Emulsion Interface-Initiated ATRP. J. Polym. Sci., Part A: Polym. Chem. 2009, 47 (5), 1354-1367, 10.1002/pola.23244
31. Bondeson, D.; Mathew, A.; Oksman, K. Optimization of the Isolation of Nanocrystals from Microcrystalline Cellulose by Acid Hydrolysis. Cellulose 2006, 13 (2), 171, 10.1007/s10570-006-9061-4
32. Brand, J.; Pecastaings, G.; Sèbe, G. A Versatile Method for the Surface Tailoring of Cellulose Nanocrystal Building Blocks by Acylation with Functional Vinyl Esters. Carbohydr. Polym. 2017, 169, 189-197, 10.1016/j.carbpol.2017.03.077
33. Min, K. et al. AGET ATRP in the Presence of Air in Miniemulsion and in Bulk. Macromol. Rapid Commun. 2006, 27 (8), 594-598, 10.1002/marc.200600060
34. Morandi, G.; Heath, L.; Thielemans, W. Cellulose Nanocrystals Grafted with Polystyrene Chains through Surface-Initiated Atom Transfer Radical Polymerization (SI-ATRP). Langmuir 2009, 25 (14), 8280-8286, 10.1021/la900452a
35. Tesch, S.; Gerhards, C.; Schubert, H. Stabilization of Emulsions by OSA Starches. J. Food Eng. 2002, 54 (2), 167-174, 10.1016/S0260-8774(01)00206-0
36. Zhang, Z.; Tam, K. C.; Wang, X.; Sèbe, G. Inverse Pickering Emulsions Stabilized by Cinnamate Modified Cellulose Nanocrystals as Templates To Prepare Silica Colloidosomes. ACS Sustainable Chem. Eng. 2018, 6 (2), 2583-2590, 10.1021/acssuschemeng.7b04061
37. Zhang, Z.; Tam, K. C.; Sèbe, G.; Wang, X. Convenient Characterization of Polymers Grafted on Cellulose Nanocrystals via SI-ATRP without Chain Cleavage. Carbohydr. Polym. 2018, 199, 603-609, 10.1016/j.carbpol.2018.07.060
38. Finkle, P.; Hildebrand, J. H. et al. The Theory of Emulsification. J. Am. Chem. Soc. 1923, 45, 2780-2788, 10.1021/ja01665a002
39. Destribats, M.; Gineste, S.; Laurichesse, E.; Tanner, H.; Leal-Calderon, F.; Héroguez, V.; Schmitt, V. Pickering Emulsions: What Are the Main Parameters Determining the Emulsion Type and Interfacial Properties?. Langmuir 2014, 30 (31), 9313-9326, 10.1021/la501299u
40. Arditty, S.; Whitby, C. P.; Binks, B. P.; Schmitt, V.; Leal-Calderon, F. Some General Features of Limited Coalescence in Solid-Stabilized Emulsions. Eur. Phys. J. E: Soft Matter Biol. Phys. 2003, 11 (3), 273-281, 10.1140/epje/i2003-10018-6
41. Bombalski, L.; Min, K.; Dong, H.; Tang, C.; Matyjaszewski, K. Preparation of Well-Defined Hybrid Materials by ATRP in Miniemulsion. Macromolecules 2007, 40 (21), 7429-7432, 10.1021/ma071408k
42. Min, K.; Gao, H.; Matyjaszewski, K. Preparation of Homopolymers and Block Copolymers in Miniemulsion by ATRP Using Activators Generated by Electron Transfer (AGET). J. Am. Chem. Soc. 2005, 127 (11), 3825-3830, 10.1021/ja0429364
43. Gillies, M. B.; Matyjaszewski, K.; Norrby, P.-O.; Pintauer, T.; Poli, R.; Richard, P. A DFT Study of R-X Bond Dissociation Enthalpies of Relevance to the Initiation Process of Atom Transfer Radical Polymerization. Macromolecules 2003, 36 (22), 8551-8559, 10.1021/ma0351672
44. Drappier, C. Biofunctional self-assemblies from polymer-b-peptide conjugates; Bordeaux: Bordeaux, 2013.