Targeting copolymer composition distribution via model-based monomer feeding policy in semibatch RAFT mini-emulsion copolymerization of styrene and butyl acrylate

Industrial and Engineering Chemistry Research

Volumn 53, Issue 18, 2014, Pages 7321-7332

  Li, Xiaohui ^a   Wang, Wen Jun ^a,b   Weng, Feiyin ^a   Li, Bo Geng ^a   Zhu, Shiping ^c  

^a ZHEJIANG UNIVERSITY   (China)

^b ZHEJIANG UNIVERSITY   (China)

^c MCMASTER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BATCH REACTORS; COPOLYMERIZATION; EMULSIFICATION; EMULSION POLYMERIZATION; KINETIC PARAMETERS; KINETIC THEORY; MONOMERS; POLYMERS; STYRENE;

CONTROLLED/LIVING RADICAL POLYMERIZATION; COPOLYMER COMPOSITIONS; HETEROGENEOUS SYSTEMS; HOMOGENEOUS SYSTEM; MINI-EMULSION POLYMERIZATION; POLYMERIZATION KINETICS; REVERSIBLE ADDITION-FRAGMENTATION TRANSFERS; SEMIBATCH REACTOR;

COPOLYMERS;

EID: 84900418114     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie402799u     Document Type: Article

References (82)

1. Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Narrow Molecular Weight Resins by a Free-Radical Polymerization Process Macromolecules 1993, 26, 2987
2. Moad, G.; Rizzardo, E.; Solomon, D. H. Selectivity of the Reaction of Free Radicals with Styrene Macromolecules 1982, 15, 909
3. Wang, J. S.; Matyjaszewski, K. Controlled Living Radical Polymerization-Atom Transfer Radical Polymerization in the Presence of Transition-Metal Complexes J. Am. Chem. Soc. 1995, 117, 5614
4. Patten, T. E.; Matyjaszewski, K. Atom Transfer Radical Polymerization and the Synthesis of Polymeric Materials Adv. Mater. 1998, 12, 901
5. Li, X.; Wang, W. J.; Li, B. G.; Zhu, S. Kinetic and Modeling of Solution ARGET ATRP of Styrene, Butyl Acrylate, and Methyl Methacrylate Macromol. React. Eng. 2011, 5, 467
6. Chiefari, J.; Chong, Y. K.; Ercole, F.; Krstina, J.; Jeffery, J.; Le, T. P. T.; Mayadunne, R. T. A.; Meijs, G. F.; Moad, C. L.; Moad, G.; Rizzardo, E.; Thang, S. H. Living Free-radical Polymerization by Reversible Addition-fragmentation Chain Transfer: The RAFT Process Macromolecules 1998, 31, 5559
7. Chong, Y. K.; Le, T. P. T.; Moad, G.; Rizzardo, E.; Thang, S. H. A More Versatile Route to Block Copolymers and Other Polymers of Complex Architecture by Living Radical Polymerization: The RAFT Process. Macromolecules 1999, 32, 2071.
8. Wang, D.; Li, X.; Wang, W. J.; Gong, X.; Li, B. G.; Zhu, S. Kinetics and Modeling of Semi-batch RAFT Copolymerization with Hyperbranching Macromolecules 2012, 45, 28
9. Matyjaszewski, K. Architecturally Complex Polymers with Controlled Heterogeneity Science 2011, 333, 1104
10. Matyjaszewski, K.; Xia, J. Atom Transfer Radical Polymerization Chem. Rev. 2001, 101, 2921
11. Wang, W. J.; Liu, P.; Li, B. G.; Zhu, S. One-step Synthesis of Hyperbranched Polyethylene Macroinitiator and Its Block Copolymers with Methyl Methacrylate or Styrene via ATRP J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 3024
12. Wang, W. J.; Wang, D.; Li, B. G.; Zhu, S. Synthesis and Characterization of Hyperbranched Polyacrylamide Using Semibatch Reversible Addition- fragmentation Chain Transfer (RAFT) Polymerization Macromolecules 2010, 43, 4062
13. Wang, D.; Wang, W. J.; Li, B. G.; Zhu, S. Semibatch RAFT Polymerization for Branched Polyacrylamide Production: Effect of Divinyl Monomer Feeding Policies AIChE J. 2013, 59, 1322
14. Ye, Y.; Schork, F. J. Modeling and Control of Sequence Length Distribution for Controlled Radical (RAFT) Copolymerization Ind. Eng. Chem. Res. 2009, 48, 10827
15. Wang, L.; Broadbelt, L. J. Model-Based Design for Preparing Styrene/Methyl Methacrylate Structural Gradient Copolymers Macromol. Theory Simul. 2011, 20, 191
16. Pickett, G. T. Linear Gradient Copolymer Melt Brushes J. Chem. Phys. 2003, 118, 3898
17. Jiang, R.; Jin, Q.; Li, B.; Ding, D.; Wickham, R. A.; Shi, A. C. Phase Behavior of Gradient Copolymers Macromolecules 2008, 41, 5457
18. Matyjaszewski, K. Macromolecular Engineering: From Rational Design through Precise Macromolecular Synthesis and Process to Targeted Macroscopic Material Properties Prog. Polym. Sci. 2005, 30, 858
19. Zhao, Y.; Luo, Y. W.; Li, B. G.; Zhu, S. pH Responsivity and Micelle Formation of Gradient Copolymers of Methacrylic Acid and Methyl Methacrylate in Aqueous Solution Langmuir 2011, 27, 11306
20. Wang, R.; Luo, Y. W.; Li, B. G.; Sun, X.; Zhu, S. Design and Control of Copolymer Composition Distribution in Living Radical Polymerization Using Semi-batch Feeding Policies: A Model Simulation Macromol. Theory Simul. 2006, 15, 356
21. Wang, R.; Luo, Y. W.; Li, B. G.; Zhu, S. Control of Gradient Copolymer Composition in ATRP Using Semi-batch Feeding Policy AIChE J. 2007, 53, 174
22. Sun, X.; Luo, Y.; Wang, R.; Li, B. G.; Liu, B.; Zhu, S. Programmed Synthesis of Copolymer with Controlled Chain Composition Distribution via Semibatch RAFT Copolymerization Macromolecules 2007, 40, 849
23. Sun, X.; Luo, Y.; Wang, R.; Li, B. G.; Zhu, S. Semibatch RAFT Polymerization for Producing ST/BA Copolymers with Controlled Gradient Composition Profiles AIChE J. 2008, 54, 1073
24. Zhao, Y.; Luo, Y. W.; Ye, C.; Li, B. G.; Zhu, S. Model-based Design and Synthesis of Gradient MMA/tBMA Copolymers by Computer-programmed Semibatch Atom Transfer Radical Copolymerization J. Polym. Sci., Part A: Polym. Chem. 2009, 47, 69
25. Asua, J. M. Miniemulsion Polymerization Prog. Polym. Sci. 2002, 27, 1283
26. Zetterlund, P. B.; Kagawa, Y.; Okubo, M. Controlled/living Radical Polymerization in Dispersed Systems Chem. Rev. 2008, 108, 3747
27. Monteiro, M. J.; Cunningham, M. F. Polymer Nanoparticles via Living Radical Polymerization in Aqueous Dispersion: Design and Applications Macromolecules 2012, 45, 4939
28. Farcet, C.; Lansalot, M.; Pirri, R.; Vairon, J. P.; Charleux, B. Polystyrene-block-poly(butyl acrylate) and Polystyrene-block-poly[(butyl acrylate)-co-styrene] Block Copolymers Prepared via Controlled Free-radical Miniemulsion Polymerization Using Degenerative Iodine Transfer Macromol. Rapid Commun. 2000, 21, 921
29. Luo, Y.; Liu, X. Reversible Addition-fragmentation Transfer (RAFT) Copolymerization of Methyl methacrylate and Styrene in Miniemulsion J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 6248
30. Zhang, Q.; Zhan, X.; Chen, F.; Shi, Y.; Wang, Q. Block Copolymers of Dodecafluoroheptyl Methacrylate and Butyl Methacrylate by RAFT Miniemulsion Polymerization J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 1585
31. Min, K.; Oh, J. K.; Matyjaszewski, K. Preparation of Gradient Copolymers via ATRP in Miniemulsion. II. Forced Gradient J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 1413
32. Urretabizkaia, A.; Leiza, J. R.; Asua, J. M. On-Line Terpolymer Composition Control in Semicontinuous Emulsion Polymerization AIChE J. 1994, 40, 1850
33. de Buruaga, I. S.; Echevarría, A.; Armitage, P. D.; de la Cal, J. C.; Leiza, J. R.; Asua, J. M. On-Line Control of a Semibatch Emulsion Polymerization Reactor Based on Calorimetry AIChE J. 1997, 43, 1069
34. de Buruaga, I. S.; Leiza, J. R.; Asua, J. M. Model-based Control of Emulsion Terpolymers Based on Calorimetric Measurements Polym. React. Eng. 2000, 8, 39
35. Vicente, M.; Leiza, J. R.; Asua, J. M. Simultaneous Control of Copolymer Composition and MWD in Emulsion Copolymerization AIChE J. 2001, 47, 1594
36. Arzamendi, G.; Asua, J. M. Monomer Addition Policies for Copolymer Composition Control in Semicontinuous Emulsion Copolymerization J. Appl. Polym. Sci. 1989, 38, 2019
37. Canu, P.; Canegallo, S.; Morbidelli, M.; Storti, G. Composition Control in Emulsion Copolymerization. I. Optimal Monomer Feed Policies J. Appl. Polym. Sci. 1994, 54, 1899
38. Canegallo, S.; Canu, P.; Morbidelli, M.; Storti, G. Composition Control in Emulsion Copolymerization. II. Application to Binary and Ternary J. Appl. Polym. Sci. 1994, 54, 1919
39. Saldivar, E.; Ray, W. H. Control of Semicontinuous Emulsion Copolymerization Reactors AIChE J. 1997, 43, 2021
40. Ma, J. W.; Smith, J. A.; McAuley, K. B.; Cunningham, M. F.; Keoshkerian, B.; Georges, M. K. Nitroxide-mediated Radical Polymerization of Styrene in Miniemulsion: Model Studies of Alkoxyamine-initiated Systems Chem. Eng. Sci. 2003, 58, 1163
41. Ma, J. W.; Cunningham, M. F.; McAuley, K. B.; Keoshkerian, B.; Georges, M. Nitroxide-mediated Living Radical Polymerization of Styrene in Miniemulsion-Modelling Persulfate-initiated Systems Chem. Eng. Sci. 2003, 58, 1177
42. Ma, J. W.; Cunningham, M. F.; McAuley, K. B.; Keoshkerian, B.; Georges, M. K. Model Studies of Nitroxide-mediated Styrene Miniemulsion Polymerization-Opportunities for Process Improvement Macromol. Theory Simul. 2003, 12, 72
43. Luo, Y.; Wang, R.; Yang, L.; Yu, B.; Li, B.; Zhu, S. Effect of Reversible Addition-fragmentation Transfer (RAFT) Reactions on (Mini)emulsion Polymerization Kinetics and Estimate of RAFT Equilibrium Constant Macromolecules 2006, 39, 1328
44. Zetterlund, P. B.; Okubo, M. Compartmentalization in Nitroxide-mediated Radical Polymerization in Dispersed Systems Macromolecules 2006, 39, 8959
45. Zetterlund, P. B.; Okubo, M. Compartmentalization in TEMPO-mediated Radical Polymerization in Dispersed Systems: Effects of Macroinitiator Concentration Macromol. Theory Simul. 2007, 16, 221
46. Zetterlund, P. B.; Kagawa, Y.; Okubo, M. Compartmentalization in Atom Transfer Radical Polymerization of Styrene in Dispersed System: Effects of Target Molecular Weight and Halide End Group Macromolecules 2009, 42, 2488
47. Zetterlund, P. B. Compartmentalization in Atom Transfer Radical Polymerization to High Conversion in Dispersed Systems: Effects of Diffusion-controlled Reactions Macromolecules 2010, 43, 1387
48. Thomson, M. E.; Cunningham, M. F. Compartmentalization Effects on the Rate of Polymerization and the Degree of Control in ATRP Dispersed Phase Polymerization Macromolecules 2010, 43, 2772
49. Tobita, H. RAFT Miniemulsion Polymerization Kinetics, 1-Polymerization Rate Macromol. Theory Simul. 2009, 18, 108
50. Tobita, H. RAFT Miniemulsion Polymerization Kinetics, 2-Molecular Weight Distribution Macromol. Theory Simul. 2009, 18, 120
51. Tobita, H. Fundamentals of RAFT Miniemulsion Polymerization Kinetics Macromol. Symp. 2010, 288, 16
52. Tobita, H. Modeling Controlled/living Radical Polymerization Kinetics: Bulk and Miniemulsion Macromol. React. Eng. 2010, 4, 643
53. Tobita, H. Effects of Fluctuation and Segregation in the Rate Acceleration of ATRP Miniemulsion Polymerization Macromol. Theory Simul. 2011, 20, 179
54. Jung, S. M.; Gomes, V. G. Miniemulsion Polymerization via Reversible Addition-fragmentation Chain Transfer in Pseudo-bulk Regime Macromol. React. Eng. 2011, 5, 303
55. Davis, T. P.; O'Driscoll, K. F.; Piton, M. C.; Winnik, M. A. Copolymerization Propagation Kinetics of Styrene with Alkyl Acrylates Polym. Int. 1991, 24, 65
56. Coote, M. L.; Davis, T. P. The Mechanism of the Propagation Step in Free-Radical Copolymerization Prog. Polym. Sci. 1999, 24, 1217
57. Li, B.; Brooks, B. W. Prediction of Average Number of Radicals per Particle for Emulsion Polymerization J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 2397
58. Forcada, J.; Asua, J. M. Modeling of Unseeded Emulsion Copolymerization of Styrene and Methyl Methacrylate J. Polym. Sci., Part A: Polym. Chem. 1990, 28, 987
59. Nomura, M. Emulsion Polymerization; Academic Press: New York, 1982.
60. Delgado, J.; El-Aasser, M. S.; Vanderhoff, J. W. Miniemulsion Copolymerization of Vinyl Acetate and Butyl Acrylate. I. Different between the Miniemulsion Copolymerization and the Emulsion Copolymerization Processes J. Polym. Sci., Part A: Polym. Chem. 1986, 24, 861
61. Delgado, J.; El-Aasser, M. S.; Silebi, C. A.; Vanderhoff, J. W.; Guillot, J. Miniemulsion Copolymerization of Vinyl Acetate and Butyl Acrylate. II. Mathematical Model for the Monomer Transport J. Polym. Sci., Part B: Polym. Phys. 1988, 26, 1495
62. Gao, J.; Penlidis, A. Mathematical Modeling and Computer Simulation/database for Emulsion Polymerizations Prog. Polym. Sci. 2002, 27, 403
63. Wang, A. R.; Zhu, S. Modeling the Reversible Addition-Fragmentation Transfer Polymerization Process J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 1553
64. Wang, A. R.; Zhu, S. Effects of Diffusion-Controlled Radical Reactions on RAFT Polymerization Macromol. Theory Simul. 2003, 12, 196
65. Tobita, H.; Hamielec, A. E. A Kinetic Model for Network Formation in Free Radical Polymerization Makromol. Chem., Macromol. Symp. 1988, 20/21, 501
66. Jesberger, M.; Barner, L.; Stenzel, M. H.; Malmstrom, E.; Davis, T. P.; Barner-Kowollik, C. Hyperbranched Polymers as Scaffolds for Multifunctional Reversible Addition-fragmentation Chain-transfer Agents: A Route to Polystyrene-core-polyesters and Polystyrene-block-poly(butyl acrylate)-core-polyesters J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 3847
67. Li, D.; Hutchinson, R. A. Penultimate Propagation Kinetics of Butyl Methacrylate, Butyl Acrylate, and Styrene Terpolymerization Macromol. Rapid Commun. 2007, 28, 1213
68. Gilbert, R. G. Emulsion Polymerization: A Mechanistic Approach; Academic Press: London, 1995.
69. Buback, M.; Gilbert, R. G.; Hutchinson, R. A.; Klumperman, B.; Kuchta, F.; Mander, B. G.; O'Driscoll, K. F.; Russell, G. T.; Schweer, J. Critically Evaluated Rate Coefficient for Styrene Macromol. Chem. Phys. 1995, 196, 3267
70. Beuermann, S.; Paquet, D. A., Jr.; McMinn, J. H.; Hutchinson, R. A. Determination of Free-Radical Propagation Rate Coefficient of Butyl, 2-Ethylhexyl, and Dodecyl Acrylates by Pulsed-Laser Polymerization Macromolecules 1996, 29, 4206
71. Hui, A. W.; Hamiclec, A. E. Thermal Polymerization of Styrene at High Conversions and Temperatures: An Experimental Study J. Appl. Polym. Sci. 1972, 16, 749
72. Li, D.; Grady, M. C.; Hutchinson, R. A. High-temperature Semibatch Free Radical Copolymerization of Butyl Methacrylate and Butyl Acrylate Ind. Eng. Chem. Res. 2005, 44, 2506
73. Keramopoulos, A.; Kiparissides, C. Development of a Comprehensive Model for Diffusion-Controlled Free-Radical Copolymerization Reactions Macromolecules 2002, 35, 4155
74. Keramopoulos, A.; Kiparissides, C. Mathematical Modeling of Diffusion-Controlled Free-Radical Terpolymerization Reactions J. Appl. Polym. Sci. 2003, 88, 161
75. Zhang, M.; Ray, W. H. Modeling of "Living" Free-Radical Polymerization Processes. I. Batch, Semibatch, and Continuous Tank Reactors J. Appl. Polym. Sci. 2002, 86, 1630
76. Walling, C. Copolymerization. XIII. Overall Rates in Copolymerization. Polar Effects in Chain Initiation and Termination J. Am. Chem. Soc. 1949, 71, 1930
77. Penboss, I. A.; Gilbert, R. G.; Napper, D. H. Entry Rate Coefficients in Emulsion Polymerization Systems J. Chem. Soc. Faraday Trans. 1986, 82, 2247
78. Kostanski, L. K.; Hamiclec, A. E. Influence of Temperature on Butyl Acrylate-Styrene Copolymerization Parameters Polymer 1992, 33, 3706
79. Prindle, J. C., Jr. Dynamics and Stability of Emulsion Polymerization Reactors. Ph.D. Thesis, University of Wisconsin-Madison: Madison, WI, 1989.
80. Unzueta, E.; Forcada, J. Modeling the Effect of Mixed Emulsifier Systems in Emulsion Copolymerization J. Appl. Polym. Sci. 1997, 66, 445
81. Asua, J. M.; Sudol, E. D.; El-Aasser, M. S. Radical Desorption in Emulsion Polymerization J. Polym. Sci., Part A: Polym. Chem. 1989, 27, 3903
82. Wilke, C. R.; Chang, P. Correlation of Diffusion Coefficients in Dilute Solutions AIChE J. 1955, 1, 264