Grafting of cellulose by ring-opening polymerisation - A review

European Polymer Journal

Volumn 48, Issue 10, 2012, Pages 1646-1659

  Carlmark, Anna ^a   Larsson, Emma ^a   Malmström, Eva ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

Biocomposites; Cellulose; Cellulose derivatives; Ring opening polymerization (ROP); Surface grafting

Indexed keywords

AMPHIPHILIC MATERIALS; BARRIER PROPERTIES; BIO-COMPOSITES; BIORENEWABLE; CAPROLACTONE; CELLULOSE NANOCRYSTALS; CELLULOSE SUBSTRATES; FIBRILLAR STRUCTURES; GRAFTING FROM; INTERFACIAL PROPERTY; L-LACTIDE; MICROFIBRILLATED CELLULOSE; POLYMER MATRICES; REINFORCING ELEMENTS; RING OPENING; SURFACE GRAFTED; SURFACE GRAFTING; SYNTHETIC MATERIALS;

CELLULOSE DERIVATIVES; COMPOSITE MATERIALS; GRAFTING (CHEMICAL); MATERIALS PROPERTIES; MECHANICAL PROPERTIES; POLYMERIZATION; POLYMERS;

CELLULOSE;

CELLULOSE DERIVATIVES; COMPOSITES; MECHANICAL PROPERTIES; POLYMERIZATION; POLYMERS;

EID: 84866058398     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2012.06.013     Document Type: Review

References (56)

1. D. Roy, M. Semsarilar, J.T. Guthrie, and S. Perrier Cellulose modification by polymer grafting: a review Chem Soc Rev 38 7 2009 2046 2064
2. D. Klemm, B. Heublein, H.-P. Fink, and A. Bohn Cellulose: fascinating biopolymer and sustainable raw material Angew Chem Int Ed 44 22 2005 3358 3393
3. S.J. Eichhorn, A. Dufresne, M. Aranguren, N.E. Marcovich, J.R. Capadona, and S.J. Rowan Review: current international research into cellulose nanofibres and nanocomposites J Mater Sci 45 1 2010 1 33
4. D.N. Saheb, and J.P. Jog Natural fiber polymer composites: a review Adv Polym Technol 18 4 1999 351 363
5. Lönnberg H. Ring-Opening Polymerization from Cellulose for Biocomposite Applications [Doctoral Thesis]. Stockholm: KTH Royal Institute of Technolology; 2009.
6. S.J. Eichhorn, C.A. Baillie, N. Zafeiropoulos, L.Y. Mwaikambo, M.P. Ansell, and A. Dufresne Review: current international research into cellulosic fibres and composites J Mater Sci 36 9 2001 2107 2131
7. M. Tizzotti, A. Charlot, E. Fleury, M. Stenzel, and J. Bernard Modification of polysaccharides through controlled/living radical polymerization grafting-towards the generation of high performance hybrids Macromol Rapid Commun 31 20 2010 1751 1772
8. J. George, M.S. Sreekala, and S. Thomas A review on interface modification and characterization of natural fiber reinforced plastic composites Polym Eng Sci 41 9 2001 1471 1485
9. E. Malmström, and A. Carlmark Controlled grafting of cellulose fibres - an outlook beyond paper and cardboard Polym Chem 3 3 2012 727 733
10. I. Siro, and D. Plackett Microfibrillated cellulose and new nanocomposite materials: a review Cellulose 17 3 2010 459 494
11. D. Klemm, F. Kramer, S. Moritz, T. Lindström, M. Ankerfors, and D. Gray Nanocelluloses: a new family of nature-based materials Angew Chem Int Ed 50 24 2011 5438 5466
12. J. Zhu, W.-T. Wang, X.-L. Wang, B. Li, and Y.-Z. Wang Green synthesis of a novel biodegradable copolymer base on cellulose and poly(p-dioxanone) in ionic liquid Carbohydrate Polym 76 1 2009 139 144
13. C. Yan, J. Zhang, Y. Lv, J. Yu, J. Wu, and J. Zhang Thermoplastic cellulose-graft-poly (l-lactide) copolymers homogeneously synthesized in an ionic liquid with 4-dimethylaminopyridine catalyst Biomacromolecules 10 8 2009 2013 2018
14. A.K. Bledzki, and J. Gassan Composites reinforced with cellulose based fibres Prog Polym Sci 24 1999 221 274
15. C. Jerome, and P. Lecomte Recent advances in the synthesis of aliphatic polyesters by ring-opening polymerization Adv Drug Deliv Rev 60 9 2008 1056 1076
16. Dubois P, Coulembier O, Raquez J.-M, editors. Handbook of Ring-Opening Polymerization, 2009.
17. O. Dechy-Cabaret, B. Martin-Vaca, and D. Bourissou Controlled ring-opening polymerization of lactide and glycolide Chem Rev (Washington, DC, United States) 104 12 2004 6147 6176
18. J. Hafren, and A. Cordova Direct organocatalytic polymerization from cellulose fibers Macromol Rapid Commun 26 2 2005 82 86
19. A. Cordova, and J. Hafren Direct organic acid-catalyzed polyester derivatization of lignocellulosic material Nord Pulp Pap Res J l 20 4 2005 477 480
20. J. Hafren, and A. Cordova Direct Bronsted acid-catalyzed derivatization of cellulose with poly(l-lactic acid) and d-mandelic acid Nord Pulp Pap Res 22 2 2007 184 187
21. H. Lönnberg, Q. Zhou, H. Brumer III, T. Teeri, E. Malmström, and A. Hult Grafting of cellulose fibers with poly (Îμ-caprolactone) and poly (l-lactic acid) via ring-opening polymerization Biomacromolecules 7 7 2006 2178 2185
22. Q. Zhou, L. Greffe, M.J. Baumann, E. Malmström, T.T. Teeri, and H. Brumer III Use of xyloglucan as a molecular anchor for the elaboration of polymers from cellulose surfaces: a general route for the design of biocomposites Macromolecules 38 9 2005 3547 3549
23. Q. Yang, X. Pan, F. Huang, and K. Li Synthesis and characterization of cellulose fibers grafted with hyperbranched poly(3-methyl-3-oxetanemethanol) Cellulose (Dordrecht, Netherlands) 18 6 2011 1611 1621
24. H. Lönnberg, L. Fogelström, L. Berglund, E. Malmström, and A. Hult Surface grafting of microfibrillated cellulose with poly (Îμ-caprolactone) - Synthesis and characterization Eur Polym J 44 9 2008 2991 2997
25. H. Lönnberg, L. Fogelström, Q. Zhou, A. Hult, L. Berglund, and E. Malmström Investigation of the graft length impact on the interfacial toughness in a cellulose/poly(epsilon-caprolactone) bilayer laminate Comp Sci Technol 71 1 2011 9 12
26. H. Lönnberg, K. Larsson, T. Lindström, A. Hult, and E. Malmström Synthesis of polycaprolactone-grafted microfibrillated cellulose for use in novel bionanocomposites-influence of the graft length on the mechanical properties Acs Appl Mater Interface 3 5 2011 1426 1433
27. A.-L. Goffin, J.-M. Raquez, E. Duquesne, G. Siqueira, Y. Habibi, and A. Dufresne From interfacial ring-opening polymerization to melt processing of cellulose nanowhisker-filled polylactide-based nanocomposites Biomacromolecules 12 7 2011 2456 2465
28. N. Lin, G. Chen, J. Huang, A. Dufresne, and P.R. Chang Effects of polymer-grafted natural nanocrystals on the structure and mechanical properties of poly(lactic acid): a case of cellulose whisker-graft-polycaprolactone J Appl Polym Sci 113 5 2009 3417 3425
29. M. Labet, and W. Thielemans Improving the reproducibility of chemical reactions on the surface of cellulose nanocrystals: ROP of -caprolactone as a case study Cellulose (Dordrecht, Netherlands) 18 3 2011 607 617
30. N. Nordgren, H. Lönnberg, A. Hult, E. Malmström, and M.W. Rutland ACS Appl Mater Interfaces 1 10 2009 2098 2103
31. L. Carlsson, S. Utsel, L. Wågberg, E. Malmström, and A. Carlmark Surface-initiated ring-opening polymerization from cellulose model surfaces monitored by a quartz crystal microbalance Soft Matter 8 2 2012 512 517
32. N. Tsubokawa, T. Iida, and T. Takayama Modification of cellulose powder surface by grafting of polymers with controlled molecular weight and narrow molecular weight distribution J Appl Polym Sci 75 4 2000 515 522
33. G.L. Zhao, J. Hafren, L. Deiana, and A. Cordova Heterogeneous "organoclick" derivatization of polysaccharides: photochemical thiol-ene click modification of solid cellulose Macromol Rapid Commun 31 8 2010 740 744
34. J. Kahovec, M. Jelinkova, and V. Janout Polymer-supported oligo(N-acetyliminoethylenes). New phase-transfer catalysts Polym Bull (Berlin, Germany) 15 6 1986 485 490
35. U. Mais, W.H. Binder, S. Knaus, and H. Gruber Synthesis and 13C CP MAS NMR spectroscopy of cellulose-graft-poly(N-acetylethylenimine) Macromol Chem Phys 201 16 2000 2115 2122
36. Y. Teramoto, and Y. Nishio Cellulose diacetate-graft-poly (lactic acid)s: synthesis of wide-ranging compositions and their thermal and mechanical properties Polymer 44 9 2003 2701 2709
37. Y. Teramoto, and Y. Nishio Biodegradable cellulose diacetate-graft- poly(l-lactide)s: thermal treatment effect on the development of supramolecular structures Biomacromolecules 5 2 2004 397 406
38. Y. Teramoto, S. Ama, T. Higeshiro, and Y. Nishio Cellulose acetate-graft-poly (hydroxyalkanoate)s: synthesis and dependence of the thermal properties on copolymer composition Macromol Chem Phys 205 14 2004 1904 1915
39. M. Yoshioka, N. Hagiwara, and N. Shiraishi Thermo-plasticization of cellulose acetates by grafting of cyclic esters Cellulose (Dordrecht, Netherlands) 6 3 1999 193 212
40. Deng W, Zhuang X, Guan K, Cheng B. Structure and thermal properties of cellulose diacetate-graft-poly(lactic acid) copolymer. Adv Mater Res (Durnten-Zurich, Switzerland). 2011;221(Advanced Polymer Science and Engineering):85-89.
41. P. Vlcek, M. Janata, P. Latalova, J. Dybal, M. Spirkova, and L. Toman Bottlebrush-shaped copolymers with cellulose diacetate backbone by a combination of ring opening polymerization and ATRP J Polym Sci Part A: Polym Chem 46 2 2007 564 573
42. F. Chang, K. Yamabuki, K. Onimura, and T. Oishi Modification of cellulose by using atom transfer radical polymerization and ring-opening polymerization Polym J (Tokyo, Japan) 40 12 2008 1170 1179
43. H.K. Reimschuessel Glass transition temperature of comblike polymers: effects of side chain length and backbone chain structure J Polym Sci Polym Chem Edition 17 8 1979 2447 2457
44. W. Xie, D. Chen, X. Fan, J. Li, P.G. Wang, and H.N. Cheng Lithium chloride as catalyst for the ring-opening polymerization of lactide in the presence of hydroxyl-containing compounds J Polym Sci Part A: Polym Chem 37 17 1999 3486 3491
45. R. Shi, and H.M. Burt Synthesis and characterization of amphiphilic hydroxypropylcellulose-graft-poly(-caprolactone) J Appl Polym Sci 89 3 2003 718 727
46. C. Wang, Y. Dong, and H. Tan Biodegradable brushlike graft polymers. I. Polymerization of -caprolactone onto water-soluble hydroxypropyl cellulose as the backbone by the protection of the trimethylsilyl group J Polym Sci Part A: Polym Chem 41 2 2002 273 280
47. C. Jiang, X. Wang, P. Sun, and C. Yang Synthesis and solution behavior of poly(-caprolactone) grafted hydroxyethyl cellulose copolymers Int J Biol Macromol 48 1 2011 210 214
48. D.L. Berthier, A. Herrmann, and L. Ouali Synthesis of hydroxypropyl cellulose derivatives modified with amphiphilic diblock copolymer side-chains for the slow release of volatile molecules Polym Chem 2 9 2011 2093 2101
49. Östmark E, Nyström D, Malmström E. Unimolecular nanocontainers prepared by ROP and subsequent ATRP from hydroxypropylcellulose. Macromolecules (Washington, DC, United States). 2008;41(12):4405-4415.
50. W. Yuan, J. Yuan, F. Zhang, and X. Xie Syntheses, characterization, and in vitro degradation of ethyl cellulose-graft-poly (-caprolactone)-block-poly (l-lactide) copolymers by sequential ring-opening polymerization Biomacromolecules 8 4 2007 1101 1108
51. Q. Yan, J. Yuan, Y. Kang, and Y. Yin Dynamic supramacromolecular self-assembly: deformable polymer fabricated nanostructures through a host-controlled approach Polym Chem 1 4 2010 423 425
52. J. Zhu, X.-T. Dong, X.-L. Wang, and Y.-Z. Wang Preparation and properties of a novel biodegradable ethyl cellulose grafting copolymer with poly (p-dioxanone) side-chains Carbohydrate Polym 80 2 2010 350 359
53. Q. Yan, J. Yuan, F. Zhang, X. Sui, X. Xie, and Y. Yin Cellulose-based dual graft molecular brushes as potential drug nanocarriers: stimulus-responsive micelles, self-assembled phase transition behavior, and tunable crystalline morphologies Biomacromolecules 10 8 2009 2033 2042
54. J. Li, W. Xie, H.N. Cheng, R.G. Nickol, and P.G. Wang Polycaprolactone-modified hydroxyethyl cellulose films prepared by lipase-catalyzed ring-opening polymerization Macromolecules 32 8 1999 2789 2792
55. T. Gustavsson Malin, V. Persson Per, T. Iversen, K. Hult, and M. Martinelle Polyester coating of cellulose fiber surfaces catalyzed by a cellulose-binding module-Candida antarctica lipase B fusion protein Biomacromolecules 5 1 2004 106 112
56. N. Petersen, and P. Gatenholm Bacterial cellulose-based materials and medical devices: current state and perspectives Appl Microbiol Biotechnol 91 5 2011 1277 1286