Grafting of model primary amine compounds to cellulose nanowhiskers through periodate oxidation

Cellulose

Volumn 19, Issue 6, 2012, Pages 2069-2079

  Dash, Rajalaxmi ^a   Elder, Thomas ^b   Ragauskas, Arthur J ^a  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

^b USDA FOREST SERVICE   (United States)

Author keywords

Amine derivative; Cellulose nanowhiskers; Dialdehyde cellulose nanowhiskers; Periodate oxidation

Indexed keywords

AFM; AMINE COMPOUNDS; AMINE DERIVATIVES; CARBONYL GROUPS; CELLULOSE NANOWHISKERS; CRYSTALLINITIES; DIALDEHYDE CELLULOSE; FTIR SPECTROSCOPY; NMR SPECTRUM; OXIDIZED CELLULOSE; PERIODATE OXIDATION; PRIMARY AMINES; REDUCTION REACTION; REGIOSELECTIVE OXIDATION; SCHIFF BASE REACTION; SODIUM PERIODATE; TITRIMETRIC ANALYSIS;

ALDEHYDES; AMINES; CELLULOSE; CHEMICAL MODIFICATION; FUNCTIONAL GROUPS; NANOWHISKERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; REGIOSELECTIVITY; SODIUM; TITRATION;

GRAFTING (CHEMICAL);

EID: 84868328600     PISSN: 09690239     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10570-012-9769-2     Document Type: Article

References (40)

1. Alonso D, Gimeno M, Olayo R, Vazquez-Torres H, Sepulveda-Sanchez JD, Shirai K (2009) Cross-linking chitosan into UV-irradiated cellulose fibers for the preparation of antimicrobial-finished textiles. Carbohydr Polym 77(3): 536-543. doi: 10. 1016/j. carbpol. 2009. 01. 027.
2. Angellier H, Molina-Boisseau S, Belgacem MN, Dufresne A (2005) Surface chemical modification of waxy maize starch nanocrystals. Langmuir 21(6): 2425-2433. doi: 10. 1021/la047530j.
3. Araki J, Wada M, Kuga S (2001) Steric stabilization of a cellulose microcrystal suspension by poly(ethylene glycol) grafting. Langmuir 17(1): 21-27. doi: 10. 1021/la001070m.
4. Azizi Samir MAS, Alloin F, Dufresne A (2005) Review of recent research into cellulosic whiskers, their properties and their application in nanocomposite field. Biomacromolecules 6(2): 612-626. doi: 10. 1021/bm0493685.
5. Beck-Candanedo S, Roman M, Gray DG (2005) Effect of reaction conditions on the properties and behavior of wood cellulose nanocrystal suspensions. Biomacromolecules 6(2): 1048-1054. doi: 10. 1021/bm049300p.
6. Bondeson D, Mathew A, Oksman K (2006) Optimization of the isolation of nanocrystals from microcrystalline cellulose by acid hydrolysis. Cellulose 13(2): 171-180. doi: 10. 1007/s10570-006-9061-4.
7. Cassano R, Trombino S, Ferrarelli T, Muzzalupo R, Tavano L, Picci N (2009) Synthesis and antibacterial activity evaluation of a novel cotton fiber (Gossypium barbadense) ampicillin derivative. Carbohydr Polym 78(3): 639-641. doi: 10. 1016/j. carbpol. 2009. 05. 030.
8. Cetin NS, Tingaut P, Ozmen N, Henry N, Harper D, Dadmun M, Sebe G (2009) Acetylation of cellulose nanowhiskers with vinyl acetate under moderate conditions. Macromol Biosci 9(10): 997-1003. doi: 10. 1002/mabi. 200900073.
9. Dash R, Ragauskas AJ (2012) Synthesis of a novel cellulose nanowhisker-based drug delivery system. RSC Adv 2(8): 3403-3409. doi: 10. 1039/c2ra01071b.
10. Dufresne A (2008) Polysaccharide nano crystal reinforced nanocomposites. Can J Chem 86(6): 484-494. doi: 10. 1139/v07-152.
11. Eichhorn SJ (2011) Cellulose nanowhiskers: promising materials for advanced applications. Soft Matter 7(2): 303-315. doi: 10. 1039/c0sm00142b.
12. El-Tahlawy KF, El-Bendary MA, Elhendawy AG, Hudson SM (2005) The antimicrobial activity of cotton fabrics treated with different crosslinking agents and chitosan. Carbohydr Polym 60(4): 421-430. doi: 10. 1016/j. carbpol. 2005. 02. 019.
13. Fujisawa S, Saito T, Isogai A (2012) Nano-dispersion of TEMPO-oxidized cellulose/aliphatic amine salts in isopropyl alcohol. Cellulose 19(2): 459-466. doi: 10. 1007/s10570-011-9648-2.
14. Gousse C, Chanzy H, Excoffier G, Soubeyrand L, Fleury E (2002) Stable suspensions of partially silylated cellulose whiskers dispersed in organic solvents. Polymer 43(9): 2645-2651. doi: 10. 1016/s0032-3861(02)00051-4.
15. Habibi Y, Chanzy H, Vignon MR (2006) TEMPO-mediated surface oxidation of cellulose whiskers. Cellulose 13(6): 679-687. doi: 10. 1007/s10570-006-9075-y.
16. Habibi Y, Lucia LA, Rojas OJ (2010) Cellulose nanocrystals: chemistry, self-assembly, and applications. Chem Rev 110(6): 3479-3500. doi: 10. 1021/cr900339w.
17. Harrisson S, Drisko GL, Malmstrom E, Hult A, Wooley KL (2011) Hybrid rigid/soft and biologic/synthetic materials: polymers grafted onto cellulose microcrystals. Biomacromolecules 12(4): 1214-1223. doi: 10. 1021/bm101506j.
18. Hasani M, Cranston ED, Gray DG (2009) Cationic surface functionalization of cellulose nanocrystals. Abstracts of Papers of the American Chemical Society 237.
19. Huang JG, Ichinose I, Kunitake T (2006) Biomolecular modification of hierarchical cellulose fibers through titania nanocoating. Angew Chem Int Ed Engl 45(18): 2883-2886. doi: 10. 1002/anie. 200503867.
20. John MJ, Thomas S (2008) Biofibres and biocomposites. Carbohydr Polym 71(3): 343-364. doi: 10. 1016/j. carbpol. 2007. 05. 040.
21. Johnson R, Zink-Sharp A, Glasser W (2011) Preparation and characterization of hydrophobic derivatives of TEMPO-oxidized nanocelluloses. Cellulose 18(6): 1599-1609. doi: 10. 1007/s10570-011-9579-y.
22. Kim UJ, Kuga S, Wada M, Okano T, Kondo T (2000) Periodate oxidation of crystalline cellulose. Biomacromolecules 1(3): 488-492. doi: 10. 1021/bm0000337.
23. Klemm D, Kramer F, Moritz S, Lindstrom T, Ankerfors M, Gray D, Dorris A (2011) Nanocelluloses: a new family of nature-based materials. Angew Chem Int Ed Engl 50(24): 5438-5466. doi: 10. 1002/anie. 201001273.
24. Kristiansen KA, Potthast A, Christensen BE (2010) Periodate oxidation of polysaccharides for modification of chemical and physical properties. Carbohydr Res 345(10): 1264-1271. doi: 10. 1016/j. carres. 2010. 02. 011.
25. Larsson PT, Hult EL, Wickholm K, Pettersson E, Iversen T (1999) CP/MAS C-13-NMR spectroscopy applied to structure and interaction studies on cellulose I. Solid State Nucl Magn Reson 15(1): 31-40. doi: 10. 1016/s0926-2040(99)00044-2.
26. Lima MMD, Borsali R (2004) Rodlike cellulose microcrystals: structure, properties, and applications. Macromol Rapid Commun 25(7): 771-787. doi: 10. 1002/marc. 200300268.
27. Majoinen J, Walther A, McKee JR, Kontturi E, Aseyev V, Malho JM, Ruokolainen J, Ikkala O (2011) Polyelectrolyte brushes grafted from cellulose nanocrystals using Cu-mediated surface-initiated controlled radical polymerization. Biomacromolecules 12(8): 2997-3006. doi: 10. 1021/bm200613y.
28. Montanari S, Rountani M, Heux L, Vignon MR (2005) Topochemistry of carboxylated cellulose nanocrystals resulting from TEMPO-mediated oxidation. Macromolecules 38(5): 1665-1671. doi: 10. 1021/ma048396c.
29. Morandi G, Heath L, Thielemans W (2009) Cellulose nanocrystals grafted with polystyrene chains through surface-initiated atom transfer radical polymerization (SI-ATRP). Langmuir 25(14): 8280-8286. doi: 10. 1021/la900452a.
30. Nair KG, Dufresne A, Gandini A, Belgacem MN (2003) Crab shell chitin whiskers reinforced natural rubber nanocomposites. 3. effect of chemical modification of chitin whiskers. Biomacromolecules 4(6): 1835-1842. doi: 10. 1021/bm030058g.
31. Park S, Baker JO, Himmel ME, Parilla PA, Johnson DK (2010) Cellulose crystallinity index: measurement techniques and their impact on interpreting cellulase performance. Biotechnology for Biofuels 3. doi: 10. 1186/1754-6834-3-10.
32. Peng BL, Dhar N, Liu HL, Tam KC (2011) Chemistry and applications of nanocrystalline cellulose and its derivatives: a nanotechnology perspective. Can J Chem Eng 89(5): 1191-1206. doi: 10. 1002/cjce. 20554.
33. Peresin MS, Habibi Y, Zoppe JO, Pawlak JJ, Rojas OJ (2010) Nanofiber composites of polyvinyl alcohol and cellulose nanocrystals: manufacture and characterization. Biomacromolecules 11(3): 674-681. doi: 10. 1021/bm901254n.
34. Potthast A, Kostic M, Schiehser S, Kosma P, Rosenau T (2007) Studies on oxidative modifications of cellulose in the periodate system: molecular weight distribution and carbonyl group profiles. Holzforschung 61(6): 662-667. doi: 10. 1515/hf. 2007. 099.
35. Ringot C, Sol V, Barriere M, Saad N, Bressollier P, Granet R, Couleaud P, Frochot C, Krausz P (2011) Triazinyl porphyrin-based photoactive cotton fabrics: preparation, characterization, and antibacterial activity. Biomacromolecules 12(5): 1716-1723. doi: 10. 1021/bm200082d.
36. Rohrling J, Potthast A, Rosenau T, Lange T, Borgards A, Sixta H, Kosma P (2002) A novel method for the determination of carbonyl groups in cellulosics by fluorescence labeling. 2. validation and applications. Biomacromolecules 3(5): 969-975. doi: 10. 1021/bm020030p.
37. Sassi JF, Chanzy H (1995) Ultrastructural aspects of the acetylation of cellulose. Cellulose 2(2): 111-127. doi: 10. 1007/bf00816384.
38. Siqueira G, Bras J, Dufresne A (2009) Cellulose Whiskers versus microfibrils: influence of the nature of the nanoparticle and its surface functionalization on the thermal and mechanical properties of nanocomposites. Biomacromolecules 10(2): 425-432. doi: 10. 1021/bm801193d.
39. Yuan HH, Nishiyama Y, Wada M, Kuga S (2006) Surface acylation of cellulose whiskers by drying aqueous emulsion. Biomacromolecules 7(3): 696-700. doi: 10. 1021/bm050828j.
40. Zhang J, Jiang N, Dang Z, Elder TJ, Ragauskas AJ (2008) Oxidation and sulfonation of cellulosics. Cellulose 15(3): 489-496. doi: 10. 1007/s10570-007-9193-1.