Controlled synthesis of cellulose-graft-poly[2-(diethylamino)-ethyl methacrylate] by ATRP in ionic liquid [AMIM]Cl and its pH-responsive property

European Polymer Journal

Volumn 66, Issue , 2015, Pages 228-235

  Tang, Erjun ^a   Du, Kaidi ^a   Feng, Xiaoyan ^a   Yuan, Miao ^a   Liu, Shaojie ^a   Zhao, Dishun ^a  

^a HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

ATRP; Cosolvent pH responsive; Ionic liquid; Microcrystalline cellulose

Indexed keywords

BIOMEDICAL ENGINEERING; CELLULOSE; CHLORINE COMPOUNDS; COPOLYMERS; FREE RADICAL REACTIONS; IONIC LIQUIDS; LIQUIDS; MOLECULAR WEIGHT DISTRIBUTION; SYNTHESIS (CHEMICAL);

1-ALLYL-3-METHYLIMIDAZOLIUM CHLORIDES; CONTROLLED SYNTHESIS; ETHYL METHACRYLATES; HETEROGENEOUS SYSTEMS; MICRO-CRYSTALLINE CELLULOSE; OPTIMUM REACTION CONDITIONS; PH-RESPONSIVE; SYNTHETIC MECHANISM;

ATOM TRANSFER RADICAL POLYMERIZATION;

EID: 84923792350     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2015.01.041     Document Type: Article

References (51)

1. N. Kar, H.Y. Liu, and K.J. Edgar Synthesis of cellulose adipate derivatives Biomacromolecules 12 4 2011 1106 1115 10.1021/bm101448f
2. C.F. Hsu, and P.A. Kilmartin Antioxidant capacity of robust polyaniline-ethyl cellulose films React Funct Polym 72 11 2012 814 822 10.1016/j.reactfunctpolym.2012.07.015
3. Y. Guo, J.P. Zhou, Y.B. Song, and L.N. Zhang An efficient and environmentally friendly method for the synthesis of cellulose carbamate by microwave heating Macromol Rapid Commun 30 17 2009 1504 15086 10.1002/marc.200900238
4. X. Yin, A. Koschella, and Th. Heinze Regioselectively oxidized 3-O-alkyl ethers of cellulose: synthesis and characterization React Funct Polym 69 6 2009 341 346 10.1016/j.reactfunctpolym.2009.02.010
5. M. Wang, J. Yuan, X.B. Huang, X.M. Cai, L. Li, and J. Shen Grafting of carboxybetaine brush onto cellulose membranes via surface-initiated ARGET-ATRP for improving blood compatibility Colloid Surf B 103 2013 52 58 10.1016/j.colsurfb.2012.10.025
6. W.Y. Li, A.X. Jin, C.F. Liu, R.C. Sun, A.P. Zhang, and J.F. Kennedy Homogeneous modification of cellulose with succinic anhydride in ionic liquid using 4-dimethylaminopyridine as a catalyst Carbohydr Polym 78 2009 389 395 10.1016/j.carbpol.2009.04.028
7. A.J. Carmichael, D.M. Haddleton, and S.A.F. Bon Copper(I) mediated living radical polymerisation in an ionic liquid Chem Commun 14 2005 1237 1238 10.1039/B003335I
8. J. Wu, J. Zhang, H. Zhang, J.S. He, Q. Ren, and M.L. Guo Homogeneous acetylation of cellulose in a new ionic liquid Biomacromolecules 5 2004 266 268 10.1021/bm034398d
9. H. Zhang, J. Wu, J. Zhang, and J.S. He 1-Allyl-3-methylimidazolium chloride room temperature ionic liquid: a new and powerful nonderivatizing solvent for cellulose Macromolecules 38 2005 8272 8277 10.1021/ma0505676
10. P.S. Richard, K.S. Scott, D.H. John, and R.D. Rogers Dissolution of cellulose with ionic liquids J Am Chem Soc 124 2002 4974 4985 10.1021/ja025790m
11. Q. Ren, J. Wu, J. Zhang, J.S. He, and M.L. Guo Synthesis of 1-allyl-3-methylimidazolium- based room-temperature ionic liquid and preliminary study of its dissolving cellulose Acta Polym Sin 3 2003 448 451
12. S.J. Zhang, and X.M. Lv The ionic liquids-from basic research to industrial application 2006 Science Press Beijing p. 6
13. L. Leclercq, and A. Schmitzer Supramolecular effects involving the incorporation of guest substrates in imidazolium ionic liquid networks: recent advances and future developments Supramol Chem 21 2009 245 263 10.1002/chin.201001251
14. A.R. Xu, J.J. Wang, and H.Y. Wang Effects of anionic structure and lithium salts addition on the dissolution of cellulose in 1-butyl-3-methylimidazolium-based ionic liquid solvent systems Green Chem 12 2010 268 275 10.1039/b916882f
15. H.W. Clare, T.C. Kristina, G.M. Milena, J.P. Rachel, G.M. Janis, and C. Stephen Surface modification of commercial cellulose acetate membranes using surface-initiated polymerization of 2-hydroxyethyl methacrylate to improve membrane surface biofouling resistance J Membr Sci 385-386 2011 30 39 10.1016/j.memsci.2011.09.017
16. K.C. Gupta, and Keerti Khandekar Temperature-responsive cellulose by ceric (iv)ion-initiated graft copolymerization of n-isopropylacrylamide Biomacromolecules 4 3 2003 758 765 10.1021/bm020135s
17. Yoshiyuki Nishio Material functionalization of cellulose and related polysaccharides via diverse microcompositions Adv Polym Sci 205 2006 97 151 10.1007/12 095
18. C.X. Lin, H.Y. Zhan, M.H. Liu, S.Y. Fu, and J.J. Zhang Preparation of cellulose graft poly(methyl methacrylate) copolymers by atom transfer radical polymerization in an ionic liquid Carbohydr Polym 78 3 2009 432 438 10.1016/j.carbpol.2009.04.032
19. K. Matyjaszewski, and N.V. Tsarevsky Nanostructured functional materials prepared by atom transfer radical polymerization Nat Chem 22 2009 276 288 DOI:1.138/NCHEM.257
20. W. Li, and K. Matyjaszewski Uniform PEO star polymers synthesized in water via free radical polymerization or atom transfer radical polymerization Macromol Rapid Commun 32 1 2011 74 81 10.1002/marc.201000477
21. P. Polanowski, J.K. Jeszka, and K. Matyjaszewski Synthesis of star polymers by "core-first" one-pot method via ATRP: Monte Carlo simulations Polymer 55 2014 2552 2561 10.1016/j.polymer.2014.03.049
22. K. Mukumoto, M.J. Zhong, and K. Matyjaszewski Atom transfer radical polymerization of dimethyl(methacryloyloxymethyl) phosphonate Eur Polym J 56 2014 11 16 10.1016/j.eurpolymj.2014.03.029
23. A. Boujemaoui, S. Mongkhontreerat, E. Malmström, and A. Carlmark Preparation and characterization of functionalized cellulose nanocrystals Carbohydr Polym 115 2015 457 464 10.1016/j.carbpol.2014.08.110
24. G. Morandi, L. Heath, and W. Thielemans Cellulose nanocrystals grafted with polystyrene chains through surface-initiated atom transfer radical polymerization (SI-ATRP) Langmuir 25 14 2009 8280 8286 10.1021/la900452a
25. E. Östmark, S. Harrisson, K.L. Wooley, and E.E. Malmström Comb polymers prepared by ATRP from hydroxypropyl cellulose Biomacromolecules 8 2007 1138 1148 10.1021/bm061043w
26. T. Meng, X. Gao, J. Zang, J.Y. Yuan, Y.Z. Zhang, and J.S. He Graft copolymers prepared by atom transfer radical polymerization (ATRP) from cellulose Polymer 50 2009 447 454 10.1016/j.polymer.2008.11.011
27. V. Castelvetro, M. Geppi, S. Giaiacopi, and G. Mollica Cotton fibers encapsulated with homo- and block copolymers: synthesis by the atom transfer radical polymerization grafting-from technique and solid-state NMR dynamic investigations Biomacromolecules 8 2007 498 508 10.1021/bm060602w
28. J. Lindqvist, D. Nyström, E. Östmark, P. Antoni, A. Carlmark, and M. Johansson Intelligent dual-responsive cellulose surfaces via surface-initiated ATRP Biomacromolecules 9 8 2008 2139 2145 10.1021/bm800193n
29. G. Zampano, M. Bertoldo, and S. Bronco Poly(ethyl acrylate) surface-initiated ATRP grafting from wood pulp cellulose fibers Carbohydr Polym 75 2009 22 31 10.1016/j.carbpol.2008.06.005
30. H.F. Li, H. Li, X. Zhong, X.D. Li, M.E. Gibril, and Y. Zhang Study on the chemical modification of cellulose in ionic liquid with maleic anhydride Adv Mater Res 581-582 2012 287 291 10.4028/www.scientific.net/AMR.581-582.287
31. R. Westlund, A. Carlmark, A. Hult, E. Malmstrom, and I.M. Saez Grafting liquid crystalline polymers from cellulose substrates using atom transfer radical polymerization Soft Matter 3 2007 866 871 10.1039/B700630F
32. Murat Barsbay, Olgun Gueven, H. Stenzel, and Davis Martina Verification of controlled grafting of styrene from cellulose via radiation-induced raft polymerization Macromolecules 40 20 2007 7140 7147 10.1021/ma070825u
33. D. Plackett, K. Jankova, H. Egsgaard, and S. Hvilsted Modification of jute fibers with polystyrene via atom transfer radical polymerization Biomacromolecules 6 2005 2474 2484 10.1021/bm050184f
34. L.F. Yan, and K. Ishihara Graft copolymerization of 2-methacryloyloxyethyl phosphorylcholine to cellulose in homogeneous media using atom transfer radical polymerization for providing new hemocompatible coating materials J Polym Sci A: Polym Chem 46 2008 3306 3313 10.1002/pola.22670
35. Y.Z. Guo, Q.L. Liu, H. Chen, X.H. Wang, Z.G. Shen, and X.C. Shu Direct grafting modification of pulp in ionic liquids and self-assembly behavior of the graft copolymers Cellulose 20 2013 873 884 10.1007/s10570-012-9847-5
36. S. Wan, M. Jiang, and G.Z. Zhang Dual temperature- and pH-dependent self-assembly of cellulose-based copolymer with a pair of complementary grafts Macromolecules 40 15 2007 5552 5558 10.1021/ma070147b
37. F. Bougard, M. Jeusette, L. Mespouille, P. Dubois, and R. Lazzaroni Synthesis and supramolecular organization of amphiphilic diblock and graft copolymers combining poly(N, N-dimethylamino-2-ethyl methacrylate and poly(e-caprolactone) Langmuir 23 5 2007 2339 2345 10.1021/la0620657
38. C. Gualandi, C. Duan, M.L. Focarete, M. Scandola, A. Pollicino, and G.D. Silvestro Advantages of surface-initiated ATRP (SI-ATRP) for the functionalization of electrospun materials Macromol Rapid Commun 34 1 2013 51 56 10.1002/marc.201200648
39. W.Z. Yuan, J.Y. Yuan, S.X. Zheng, and X.Y. Hong Synthesis, characterization, and controllable drug release of dendritic star-block copolymer by ring-opening polymerization and atom transfer radical polymerization Polymer 48 9 2007 2585 2594 10.1016/j.polymer.2007.03.039
40. H.H. Sokker, E.S. Abdel-Halim, A.S. Aly, and A. Hashem Cellulosic fabric wastes grafted with DMAEMA for the removal of direct dyes Adsorpt Sci Technol 22 2005 679 691 10.1260/0263617043026497
41. D. Roy, J.T. Guthrie, and S. Perrier Synthesis of natural-synthetic hybrid materials from cellulose via the RAFT process Soft Matter 4 2008 145 155 10.1039/b711248n
42. D. Roy, J.S. Knapp, J.T. Guthrie, and S. Perrier Antibacterial cellulose fiber via RAFT surface graft polymerization Biomacromolecules 9 1 2008 91 99 10.1021/bm700849j
43. S. Ananda, S. Amarasekara, Onome, and Owereh Homogeneous phase synthesis of cellulose carbamate silica hybrid materials using 1-n-butyl-3- methylimidazolium chloride ionic liquid medium Carbohydr Polym 78 2009 635 638 10.1016/j.carbpol.2009.05.032
44. Y. Li, Y.M. He, and Q.H. Fan Ionic liquids in transition metal-catalyzed enantioselective reactions Top Organomet Chem 28 2013 1436 1445 10.1007/3418-2013-60
45. D.Q. Wang, J.J. Tan, H.L. Kang, L. Ma, X. Jin, and R.G. Liu Synthesis, self-assembly and drug release behaviors of pH-responsive copolymers ethyl cellulose-graft-PDEAEMA through ATRP Carbohydr Polym 84 2011 195 202 10.1016/j.carbpol.2010.11.023
46. M. Jovanovic, Z. Grbavcic, N. Rajic, and B. Obradovic Removal of Cu(II) from aqueous solutions by using fluidized zeolite A beads: hydrodynamic and sorption studies Chem Eng Sci 117 2014 10.1016/j.ces.2014.06.017 85-72
47. Q.Y. Shang, F.Y. Yan, S.Q. Xia, Q. Wang, and P.S. Ma Predicting the surface tensions of ionic liquids by the quantitative structure property relationship method using a topological index Chem Eng Sci 101 2013 266 270 10.1016/j.ces.2013.05.053
48. T.I. Ladaa, C.M. Lee, J.T. Coates, and R.W. Falta Jr. Cosolvent effects of alcohols on the Henry's law constant and aqueous solubility of tetrachloroethylene (PCE) Chemosphere 44 2001 1137 1143 10.1016/S0045-6535(00)00472-0
49. O. Glaied, M. Dubé, C. Chabot, and Daneault Synthesis of cationic polymer-grafted cellulose by aqueous ATRP J Colloid Terf Sci 333 1 2009 145 151 10.1016/j.jcis.2009.01.050
50. A. Anastasaki, A.J. Haddleton, Q. Zhang, A. Simula, M. Droesbeke, and P. Wilson Aqueous copper-mediated living radical polymerisation of N-acryloylmorpholine, SET-LRP in water Macromol Rapid Commun 35 10 2014 965 970 10.1002/marc.201400024
51. W.Z. Yuan, J.C. Zhang, H. Zou, T.X. Shen, and J. Ren Amphiphilic ethyl cellulose brush polymers with mono and dual side chains: facile synthesis, self-assembly, and tunable temperature-pH responsivities Polymer 53 2012 956 966 10.1016/j.polymer.2012.01.003