A comprehensive kinetic model for high-temperature free radical production of styrene/methacrylate/acrylate resins

AIChE Journal

Volumn 57, Issue 1, 2011, Pages 227-238

  Wang, Wei ^a,b   Hutchinson, Robin A ^a  

^a QUEEN S UNIVERSITY   (Canada)

^b PPG INDUSTRIES   (United States)

Author keywords

Acrylate; Chain scission; Depropagation; Intramolecular transfer to polymer; Kinetics (polym.); Macromonomer reactions; Mechanistic model; Methacrylate; Midchain radical; Styrene; Terpolymerization

Indexed keywords

ACRYLATE; CHAIN SCISSION; DEPROPAGATION; INTRAMOLECULAR TRANSFER; KINETICS (POLYM.); MACROMONOMER; MECHANISTIC MODELS; METHACRYLATE; MID-CHAIN RADICALS;

FREE RADICAL POLYMERIZATION; FREE RADICALS; GROWTH KINETICS; POLYMERS; RESINS; STYRENE;

TERPOLYMERIZATION;

EID: 78650056306     PISSN: 00011541     EISSN: 15475905     Source Type: Journal    
DOI: 10.1002/aic.12258     Document Type: Article

References (58)

1. Wang W, Hutchinson RA. Recent advances in the study of high-temperature free radical acrylic solution copolymerization. Macromol React Eng. 2008; 2: 199-214.
2. Grady MC, Simosick WJ, Hutchinson RA. Studies of higher temperature polymerization of n-butyl methacrylate and n-butyl acrylate. Macromol Symp. 2002; 182: 149-168.
3. Adamsons K, Blackman G, Gregorovick B, Lin L, Matheson R. Oligomers in the evolution of automotive clearcoats: mechanical performance testing as a function of exposure. Prog Org Coat. 1998; 34: 64-74.
4. Buder-Stroisznigg M, Wallner GM, Straub B, Jandel L, Lang RW. Structure-property correlations of flexible clear coats. Prog Org Coat. 2009; 65: 328-332.
5. Bywater S. Photosensitized polymerization of methyl methacrylate in dilute solution above 100 °C. Trans Faraday Soc. 1955; 51: 1267-1273.
6. Hutchinson RA, Paquet DA Jr., Beuermann S, McMinn JH. Investigation of methacrylate free-radical depropagation kinetics by pulsed-laser polymerization. Ind Eng Chem Res. 1998; 37: 3567-3574.
7. O'Driscoll KF, Burczyk AF. Kinetics of styrene and methyl methacrylate polymerizations in a starved feed reactor. Polym React Eng. 1992; 1: 111-144.
8. Li D, Grady MC, Hutchinson RA. High-temperature semibatch free radical copolymerization of butyl methacrylate and butyl acrylate. Ind Eng Chem Res. 2005; 44: 2506-2517.
9. Wang W, Hutchinson RA, Grady MC. Study of butyl methacrylate depropagation behavior using batch experiments in combination with modeling. Ind Eng Chem Res. 2009; 48: 4810-4816.
10. Ivin KJ. Thermodynamics of addition polymerization. J Polym Sci A: Polym Chem. 2000; 38: 2137-2146.
11. Li D, Hutchinson RA. High temperature semibatch free radical copolymerization of butyl methacrylate and styrene. Macromol Symp. 2006; 243: 24-34.
12. Wang W, Hutchinson RA. High temperature semibatch free radical copolymerization of dodecyl methacrylate and styrene. Macromol Symp. 2008; 261: 64-73.
13. Lowry GG. Effect of depropagation on copolymer composition. I. General theory for one depropagating monomer. J Polym Sci. 1960; 42: 463-477.
14. Li D, Li N, Hutchinson RA. High-temperature free radical copolymerization of styrene and butyl methacrylate with depropagation and penultimate kinetic effects. Macromolecules. 2006; 39: 4366-4373.
15. Li D, Leiza JR, Hutchinson RA. High temperature free radical copolymerization with depropagation and penultimate kinetic effects. Macromol Theory Simul. 2005; 14: 554-559.
16. Ahmad NM, Heatley F, Lovell PA. Chain transfer to polymer in free-radical solution polymerization of n-butyl acrylate studied by NMR spectroscopy. Macromolecules. 1998; 31: 2822-2827.
17. Plessis C, Arzamendi G, Leiza JR, Schoonbrood AS, Charmot D, Asua JM. A decrease in effective acrylate propagation rate constants caused by intramolecular chain transfer. Macromolecules. 2000; 33: 4-7.
18. Yamada B, Azukizawa M, Yamazoe H, Hill D, Pomery P. Free radical polymerization of cyclohexyl acrylate involving interconversion between propagating and mid-chain radicals. Polymer. 2000; 41: 5611-5618.
19. Nikitin AN, Hutchinson RA. The effect of intramolecular transfer to polymer on stationary free radical polymerization of alkyl acrylates. Macromolecules. 2005; 38: 1581-1590.
20. Chiefari J, Jeffery J, Mayadunne RTA, Moad G, Rizzardo E, Thang SH. Chain transfer to polymer: a convenient route to macromonomers. Macromolecules. 1999; 32: 7700-7702.
21. Hirano T, Yamada B. Stereospecificity in radical polymerization of methyl α-(chloromethyl)acrylate. Polymer. 2003; 44: 4481-4486.
22. Peck ANF, Hutchinson RA. Secondary reactions in the high-temperature free radical polymerization of butyl acrylate. Macromolecules. 2004; 37: 5944-5951.
23. Busch M, Müller M. Simulating acrylate polymerization reactions: toward improved mechanistic understanding and reliable parameter estimates. Macromol Symp. 2004; 206: 399-418.
24. Quan C, Soroush M, Grady MC, Hansen JE. High-temperature homopolymerization of ethyl acrylate and n-butyl acrylate: polymer characterization. Macromolecules. 2005; 38: 7619-7628.
25. Rantow FS, Soroush M, Grady MC, Kalfas GA. Spontaneous polymerization and chain microstructure evolution in high-temperature solution polymerization of n-butyl acrylate. Polymer. 2006; 47: 1423-1435.
26. Junkers T, Koo SPS, Davis TP, Stenzel MH, Barner-Kowollik C. Mapping poly(butyl acrylate) product distributions by mass spectrometry in a wide temperature range: suppression of midchain radical side reactions. Macromolecules. 2007; 40: 8906-8912.
27. Junkers T, Barner-Kowollik C. The role of mid-chain radicals in acrylate free radical polymerization: branching and scission. J Polym Sci Part A: Polym Chem. 2008; 46: 7585-7605.
28. Yamada B, Oku F, Harada T. Substituted propenyl end groups as reactive intermediates in radical polymerization. J Polym Sci Part A: Polym Chem. 2003; 41: 645-654.
29. Harada T, Zetterlund PB, Yamada B. Preparation of macromonomers by copolymerization of methyl acrylate dimer involving β-fragmentation. J Polym Sci Part A: Polym Chem. 2004; 42: 597-607.
30. Wang W, Nikitin AN, Hutchinson RA. Consideration of macromonomer reactions in butyl acrylate free radical polymerization. Macromol Rapid Commun. 2009; 30: 2022-2027.
31. Wang W, Hutchinson RA. High temperature semibatch free radical copolymerization of styrene and butyl acrylate. Macromol Symp. 2010; 289: 33-42.
32. Plessis C, Arzamendi G, Leiza JR, Schoonbrood HAS, Charmot D, Asua JM. Kinetics and polymer microstructure of the seeded semibatch emulsion copolymerization of n-butyl acrylate and styrene. Macromolecules. 2001; 34: 5147-5157.
33. González I, Asua JM, Leiza JR. The role of methyl methacrylate on branching and gel formation in the emulsion copolymerization of BA/MMA. Polymer. 2007; 48: 2542-2547.
34. Gao J, Penlidis A. A comprehensive simulator/database package for bulk/solution free-radical terpolymerizations. Macromol Chem Phys. 2000; 201: 1176-1184.
35. Dubé MA, Soares JBP, Penlidis A, Hamielec AE. Mathematical modeling of multicomponent chain-growth polymerizations in batch, semibatch, and continuous reactors: a review. Ind Eng Chem Res. 1997; 36: 966-1015.
36. Keramopoulos A, Kiparissides C. Mathematical modeling of diffusion-controlled free-radical terpolymerization reactions. J Appl Polym Sci. 2003; 88: 161-176.
37. McManus NT, Hsieh G, Penlidis A. Free radical terpolymerization of butyl acrylate/methyl methacrylate and alpha methyl styrene at high temperature. Polymer. 2004; 45: 5837-5845.
38. Leamen MJ, McManus NT, Penlidis A. Terpolymerization with depropagation: modelling the copolymerization of the methyl methacrylate/alpha-methylstyrene/butyl acrylate system. Chem Eng Sci. 2006; 61: 7774-7785.
39. Wulkow M. Computer aided modeling of polymer reaction engineering-the status of Predici, 1 - simulation. Macromol React Eng. 2008; 2: 461-494.
40. Wang W, Hutchinson RA. PLP/SEC/NMR study of free radical copolymerization of styrene and glycidyl methacrylate. Macromolecules. 2008; 41: 9011-9018.
41. Penzel E, Götz N. Solution properties of polyacrylic esters. I. Light scattering and viscosity measurements in tetrahydrofuran. Angew Makromol Chem. 1990; 178: 191-200.
42. Hutchinson RA, McMinn JH, Paquet DA Jr., Beuermann S, Jackson C. A pulsed-laser study of penultimate copolymerization propagation kinetics for methyl methacrylate/n-butyl acrylate. Ind Eng Chem Res. 1997; 36: 1103-1113.
43. Seferis JC. Refractive indices of polymers. In: Brandrup J, Immergut EH, Grulke EA, editors. Polymer Handbook, 4th ed. New York: Wiley, 1999.
44. Li D. Modeling of Kinetic Complexities in High Temperature Free Radical Polymerization for Production of Acrylic Coatings Resins. PhD Thesis, Kingston, ON: Queen's University, 2006.
45. Buback M, Klingbeil S, Sandmann J, Sderra MB, Vögele HP, Wackerbarth H, Wittkowski L. Pressure and temperature dependence of the decomposition rate of tert-butyl peroxyacetate and of tert-butyl peroxypivalate. Z Phys Chem (Muenchen, Ger.). 1999; 210: 199-221.
46. Beuermann S, Buback M, Davis TP, Gilbert RG, Hutchinson RA, Kajiwara A, Klumpermann B, Russell GT. Critically evaluated rate coefficients for free-radical polymerization, 3a: propagation rate coefficients for alkyl methacrylates. Macromol Chem Phys. 2000; 201: 1355-1364.
47. Buback M, Gilbert RG, Hutchinson RA, Klumpermann B, Kuchta F, Manders BG, O'Driscoll KF, Russell GT, Schweer J. Critically evaluated rate coefficients for free-radical polymerization. 1. Propagation rate coefficient for styrene. Macromol Chem Phys. 1995; 196: 3267-3280.
48. Asua JM, Beuermann S, Buback M, Castignolles P, Charleus B, Gilbert RG, Hutchinson RA, Leiza JR, Nikitin AN, Vairon JP, van Herk AM. Critically evaluated rate coefficients for free-radical polymerization. 5. Propagation rate coefficient for butyl acrylate. Macromol Chem Phys. 2004; 205: 2151-2160.
49. Hakim M, Verhoeven V, Mcmanus NT, Dubé MA, Penlidis A. High-temperature solution polymerization of butyl acrylate/methyl methacrylate: reactivity ratio estimation. J Appl Polym Sci. 2000; 77: 602-609.
50. Li D, Hutchinson RA. Penultimate propagation kinetics of butyl methacrylate, butyl acrylate, and styrene terpolymerization. Macromol Rapid Commun. 2007; 28: 1213-1218.
51. Barth J, Buback M, Hesse P, Sergeeva T. Chain-length-dependent termination in n-butyl methacrylate and tert-butyl methacrylate bulk homopolymerizations studied via SP-PLP-ESR. Macromolecules. 2009; 42: 481-488.
52. Beuermann, S, Buback M. Rate coefficients of free-radical polymerization deduced from pulsed laser experiments. Prog Polym Sci. 2002; 27: 191-254.
53. Nikitin AN, Hutchinson RA, Wang W, Kalfas GA, Richards JR, Bruni C. Effect of intramolecular transfer to polymer on stationary free radical polymerization of alkyl acrylates, 5-consideration of solution polymerization up to high temperatures. Macromol React Eng. In press 2010.
54. Nikitin AN, Hutchinson RA, Kalfas GA, Richards JR, Bruni C. The effect of intramolecular transfer to polymer on stationary free-radical polymerization of alkyl acrylates, 3-consideration of solution polymerization up to high conversions. Macromol Theory Simul. 2009; 18: 247-258.
55. Wang W, Hutchinson RA. Evidence of scission products from peroxide-initiated higher temperature polymerization of alkyl methacrylates. Macromolecules. 2009; 42: 4910-4913.
56. Buback M, Sandmann J. Pressure and temperature dependence of the decomposition rate of aliphatic tert-butyl peroxyesters. Z Phys Chem (Muenchen, Ger). 2000; 214: 583-607.
57. Buback M, Kowollik C. Termination kinetics in free-radical bulk copolymerization: the systems dodecyl acrylate-dodecyl methacrylate and dodecyl acrylate-methyl acrylate. Macromolecules. 1999; 32: 1445-1452.
58. Buback M, Feldermann A. Termination kinetics of free-radical methyl methacrylate-dodecyl acrylate and dodecyl methacrylate-methyl acrylate copolymerizations. Aust J Chem. 2002; 55: 475-481.