Preparation and Characterization of PMMA and its Derivative via RAFT Technique in the Presence of Disulfide as a Source of Chain Transfer Agent
DOI:
https://doi.org/10.6000/1929-6037.2012.01.02.6Keywords:
Reversible addition fragmentation chain transfer (RAFT)polymerization, Theoretical molecular weight, PMMA-b-PDMAEMA, PMMA- b-PDMAEA, Disulfide compoundsAbstract
Poly(methyl methacrylate) (PMMA) were synthesized by using chain transfer agents(CTA), S-1-Dodecyl-S′-(α,α′-dimethyl-α-acetic acid) trithiocarbonate (MTTCD), S,S′-bis (2-hydroxyethyl-2′-dimethylacrylate) trithiocarbonate (BDATC), 2-cyanoprop-2-yl dithiobenzoate (CPDB) respectively, through the reversible addition fragmentation chain transfer (RAFT) polymerization under a range of synthesis conditions. The results indicated that the structure of the end-group of RAFT agents had significant effects on the ability to control polymerization. Compared with MTTCD and CPDB, BDATC can provide better control over the relative molecular mass, distribution and polymerization of PMMA. The derived well-controlled block copolymer PMMA-b-PDMAEMA and PMMA-b-PDMAEA were also successfully prepared by using N, N-dimethylaminoethy acrylate (DMAEA) or N, N-dimethylaminoethyl methacrylate (DMAEMA) as the second monomer. The chemical composition and structure of the products were characterized by FTIR, 1HNMR, XRD and DSC. CO2 and N2 permeation performance of the PMMA-b-PDMAEA/PS composite membranes were tested at different pressure. The results showed that the resulted composited membrane had a CO2 permeation rate of 3.68×10-5cm3 (STP) cm-2s-1cmHg-1, a N2 permeation rate of 1.78×10-7 cm3 (STP) cm-2s-1cmHg-1 and an ideal CO2/ N2 selectivity of 206.6 at a feed gas pressure of 7.6 cmHg and 30 oC.
References
Kaghazchi T, Gorji AH. Mathematical Modelling of Co(2) Facilitated Transport through Liquid Membranes Containing Amines as Carrier. Can J Chem Eng 2008; 86: 1039-46. http://dx.doi.org/10.1002/cjce.20107
Matsuyama H, Terada A, Nakagawara T, Kitamura Y, Teramoto M. Facilitated transport of CO2 through polyethylenimine/poly(vinyl alcohol) blend membrane. J Membrane Sci 1999; 163: 221-7. http://dx.doi.org/10.1016/S0376-7388(99)00183-0
Zhang Y, Wang Z, Wang SC. Synthesis and characteristics of novel fixed carrier membrane for CO2 separation. Chem Lett 2002; 31: 430-1. http://dx.doi.org/10.1246/cl.2002.430
Shen JN, Qiu JH, Wu LG, Gao CJ. Facilitated transport of carbon dioxide through poly (2-N,N-dimethyl aminoethyl methacrylate-co-acrylic acid sodium) membrane. Sep Purif Technol 2006; 51: 345-51. http://dx.doi.org/10.1016/j.seppur.2006.02.015
Kim MJ, Park YI, Youm KH, Lee KH. Facilitated transport of CO2 through ethylenediamine-fixed cation-exchange polysaccharide membranes. J Membrane Sci 2004; 245: 79-86. http://dx.doi.org/10.1016/j.memsci.2004.07.019
Kang SW, Kim JH, Won J, Char K, Kang YS. Effect of amino acids in polymer/silver salt complex membranes on facilitated olefin transport. J Membrane Sci 2005; 248: 201-6. http://dx.doi.org/10.1016/j.memsci.2004.08.028
Zhao J, Wang Z, Wang JX, Wang SC. Influence of heat-treatment on CO2 separation performance of novel fixed carrier composite membranes prepared by interfacial polymerization. J Membrane Sci 2006; 283: 346-56. http://dx.doi.org/10.1016/j.memsci.2006.07.004
Zhang Y, Wang Z, Wang SC. Facilitated transport of CO2 through synthetic polymeric membranes. Chinese J Chem Eng 2002;10: 570-4.
Zhang Y, Wang Z, Wang SC. Selective permeation of CO2 through new facilitated transport membranes. Desalination 2002; 145: 385-8. http://dx.doi.org/10.1016/S0011-9164(02)00441-1
Yi CH, Wang Z, Li M, Wang JX, Wang SC. Facilitated transport of CO2 through polyvinylamine/polyethlene glycol blend membranes. Desalination 2006; 193: 90-6. http://dx.doi.org/10.1016/j.desal.2005.04.139
Shen JN, Wu LG, Chen HL, Gao CJ. Separation cyclohexene/cyclohexane mixtures with facilitated transport membrane of poly(vinyl alcohol)-Co2+. Sep Purif Technol 2005; 45: 103-8. http://dx.doi.org/10.1016/j.seppur.2005.02.013
Matsuyama H, Teramoto M, Matsui K, Kitamura Y. Preparation of poly(acrylic acid)/poly(vinyl alcohol) membrane for the facilitated transport of CO2. J Appl Polym Sci 2001; 81: 936-42. http://dx.doi.org/10.1002/app.1514
Gaillard N, Claverie J, Guyot A. Synthesis and characterization of block-copolymer surfactants with specific interactions with associative thickeners. Prog Org Coat 2006; 57: 98-109. http://dx.doi.org/10.1016/j.porgcoat.2006.05.006
Gaillard N, Guyot A, Claverie J. Block copolymers of acrylic acid and butyl acrylate prepared by reversible addition-fragmentation chain transfer polymerization: Synthesis, characterization, and use in emulsion polymerization. J Polym Sci Pol Chem 2003; 41: 684-98. http://dx.doi.org/10.1002/pola.10606
Garnier S, Laschewsky A. Synthesis of new amphiphilic diblock copolymers and their self-assembly in aqueous solution. Macromolecules 2005; 38: 7580-92. http://dx.doi.org/10.1021/ma0506785
Chiefari J, Chong YK, Ercole F, et al. Living free-radical polymerization by reversible addition-fragmentation chain transfer: The RAFT process. Macromolecules 1998; 31: 5559-62. http://dx.doi.org/10.1021/ma9804951
Wang Y, Li X, Hong CY, Pan CY. Synthesis and Micellization of Thermoresponsive Galactose-Based Diblock Copolymers. J Polym Sci Pol Chem 2011; 49: 3280-90. http://dx.doi.org/10.1002/pola.24763
Song XM, Zhang YQ, Yang D, et al. Convenient Synthesis of Thermo-Responsive PtBA-g-PPEGMEMA Well-Defined Amphiphilic Graft Copolymer Without Polymeric Functional Group Transformation. J Polym Sci Pol Chem 2011; 49: 3328-37. http://dx.doi.org/10.1002/pola.24769
Boisse S, Rieger J, Pembouong G, Beaunier P, Charleux B. Influence of the Stirring Speed and CaCl2 Concentration on the Nano-Object Morphologies Obtained via RAFT-Mediated Aqueous Emulsion Polymerization in the Presence of a Water-Soluble macroRAFT Agent. J Polym Sci Pol Chem 2011; 49: 3346-54. http://dx.doi.org/10.1002/pola.24771
Mayadunne RTA, Rizzardo E, Chiefari J, et al. Living polymers by the use of trithiocarbonates as reversible addition-fragmentation chain transfer (RAFT) agents: ABA triblock copolymers by radical polymerization in two steps. Macromolecules 2000; 33: 243-5. http://dx.doi.org/10.1021/ma991451a
Mueller AHE, Schilli C, Lanzendoerfer M. Kinetic and MALDI-ToF MS investigation of the raft polymerization of n-isopropylacrylamide. Abstr Pap Am Chem S 2002; 224: 475-6.
Mayadunne RTA, Rizzardo E, Chiefari J, Chong YK, Moad G, Thang SH. Living radical polymerization with reversible addition-fragmentation chain transfer (RAFT polymerization) using dithiocarbamates as chain transfer agents. Macromolecules 1999; 32: 6977-80. http://dx.doi.org/10.1021/ma9906837
Destarac M, Charmot D, Franck X, Zard SZ. Dithiocarbamates as universal reversible addition-fragmentation chain transfer agents. Macromol Rapid Comm 2000; 21: 1035-9. http://dx.doi.org/10.1002/1521-3927(20001001)21:15<1035::AID-MARC1035>3.0.CO;2-5
Hua DB, Zhang JX, Bai R, Lu WQ, Pan CY. Controlled/living free-radical polymerization in the presence of benzyl 9H-carbazole-9-carbodithioate under (60)CO gamma-ray irradiation. Macromol Chem Phys 2004; 205: 1125-30. http://dx.doi.org/10.1002/macp.200300191
Chiefari J, Mayadunne RTA, Moad CL, et al. Thiocarbonylthio compounds (S=C(Z)S-R) in free radical polymerization with reversible addition-fragmentation chain transfer (RAFT polymerization). Effect of the activating group Z. Macromolecules 2003; 36: 2273-83. http://dx.doi.org/10.1021/ma020883+
Chong YK, Krstina J, Le TPT, et al. Thiocarbonylthio compounds [S=C(Ph)S-R] in free radical polymerization with reversible addition-fragmentation chain transfer (RAFT polymerization): Role of the free-radical leaving group (R). Macromolecules 2003; 36: 2256-72. http://dx.doi.org/10.1021/ma020882h
Hua DB, Bai RK, Lu WQ, Pan CY. Dithiocarbamate mediated controlled/living free radical polymerization of methyl acrylate under Co-60 gamma-ray irradiation: Conjugation effect of N-group. J Polym Sci Pol Chem 2004; 42: 5670-77. http://dx.doi.org/10.1002/pola.20394
Jitchum V, Perrier S. Living radical polymerization of isoprene via the RAFT process. Macromolecules 2007; 40: 1408-12. http://dx.doi.org/10.1021/ma061889s
Lai JT, Filla D, Shea R. Functional polymers from novel carboxyl-terminated trithiocarbonates as highly efficient RAFT agents. Macromolecules 2002; 35: 6754-6. http://dx.doi.org/10.1021/ma020362m
Moad G, Chiefari J, Chong YK, et al. Living free radical polymerization with reversible addition-fragmentation chain transfer (the life of RAFT). Polym Int 2000; 49: 993-1001. http://dx.doi.org/10.1002/1097-0126(200009)49:9<993::AID-PI506>3.0.CO;2-6
Smith AE, Xu XW, Mccormick CL. Stimuli-responsive amphiphilic (co)polymers via RAFT polymerization. Prog Polym Sci 2010; 35: 45-93. http://dx.doi.org/10.1016/j.progpolymsci.2009.11.005
Loiseau J, Doerr N, Suau JM, Egraz JB, Llauro MF, Ladaviere C. Synthesis and characterization of poly(acrylic acid) produced by RAFT polymerization. Application as a very efficient dispersant of CaCO3, kaolin, and TiO2. Macromolecules 2003; 36: 3066-77. http://dx.doi.org/10.1021/ma0256744
Uzulina I, Kanagasabapathy S, Claverie J. Reversible addition fragmentation transfer (RAFT) polymerization in emulsion. Macromol Symp 2000; 150: 33-38. http://dx.doi.org/10.1002/1521-3900(200002)150:1<33::AID-MASY33>3.0.CO;2-C
An QF, Qian JW, Yu LY, Luo YW, Liu XZ. Study on kinetics of controlled/living radical polymerization of acrylonitrile by RAFT technique. J Polym Sci Pol Chem 2005; 43: 1973-7. http://dx.doi.org/10.1002/pola.20622
Huang XY, Huang ZH, Huang JL. Copolymerization of styrene and vinyl acetate by successive photoinduced charge-transfer polymerization. J Polym Sci Pol Chem 2000; 38: 914-20. http://dx.doi.org/10.1002/(SICI)1099-0518(20000301)38:5<914::AID-POLA16>3.0.CO;2-K
Xue XQ, Zhu JA, Zhang ZB, Cheng ZP, Tu YF, Zhu XL. Synthesis and characterization of azobenzene-functionalized poly(styrene)-b-poly(vinyl acetate) via the combination of RAFT and "click" chemistry. Polymer 2010; 51: 3083-90. http://dx.doi.org/10.1016/j.polymer.2010.04.052
Donovan MS, Lowe AB, Sanford TA, McCormick CL. Sulfobetaine-containing diblock and triblock copolymers via reversible addition-fragmentation chain transfer polymerization in aqueous media. J Polym Sci Pol Chem 2003; 41: 1262-81. http://dx.doi.org/10.1002/pola.10658
Downloads
Published
How to Cite
Issue
Section
License
Policy for Journals/Articles with Open Access
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
- Authors are permitted and encouraged to post links to their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work
Policy for Journals / Manuscript with Paid Access
Authors who publish with this journal agree to the following terms:
- Publisher retain copyright .
- Authors are permitted and encouraged to post links to their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work .
