Investigations on the Combination of Cationic Ring Opening Polymerization and Single Electron Transfer Living Radical Polymerization to Synthesize 2-Ethyl-2-Oxazoline Block Copolymers
Robert A. Young A , Edward L. Malins A and C. Remzi Becer A BA Department of Chemistry, University of Warwick, CV4 7AL Coventry, UK.
B Corresponding author. Email: c.r.becer@warwick.ac.uk
Australian Journal of Chemistry 65(8) 1132-1138 https://doi.org/10.1071/CH12247
Submitted: 17 May 2012 Accepted: 6 June 2012 Published: 30 July 2012
Abstract
Cationic ring opening polymerization of 2-ethyl-2-oxazoline (EtOx) has been performed using α–bromoisobutyryl bromide (tertiary) and 2-bromopropionyl bromide (secondary) as initiators in acetonitrile. The reaction kinetics have been followed and selected P(EtOx) polymers have been used as macroinitiators for the single electron transfer living radical polymerization (SET-LRP) of methyl acrylate (MA), ethylene glycol methyl ether acrylate and 2-(dimethylamino)ethyl methacrylate. Moreover, the effect of solvent and catalyst concentration have been investigated on the SET-LRP of P(EtOx) initiated MA.
References
[1] J. M. Harris, R. B. Chess, Nat. Rev. Drug Discov. 2003, 2, 214.| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXhsFKrtLs%3D&md5=99f5d43b796808b027a298357dd50409CAS |
[2] R. Haag, F. Kratz, Angew. Chem. Int. Ed. 2006, 45, 1198.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhvFOqu7c%3D&md5=1c66471e7fd594d3673b33b927deea28CAS |
[3] S. N. S. Alconcel, A. S. Baas, H. D. Maynard, Polym. Chem. 2011, 2, 1442.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXotFOktrw%3D&md5=b580561fc0ee91ba2f277a63bd0051adCAS |
[4] N. Larson, H. Ghandehari, Chem. Mater. 2012, 24, 840.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XivVequg%3D%3D&md5=eec7de1d1476ad0798f7176ce0f04725CAS |
[5] H. A. Ravin, A. M. Seligman, J. Fine, New Engl. J. Med. 1952, 247, 921.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG3sXnsVSltg%3D%3D&md5=f400878ec779bf8abe63f853886747dbCAS |
[6] H. Ringsdorf, Journal of Polymer Science: Polymer Symposia 1975, 51, 135.
[7] G. Pasut, F. M. Veronese, Adv. Drug Deliv. Rev. 2009, 61, 1177.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtlWhtL7P&md5=642260ec2488b04dae7cc017cc0feba5CAS |
[8] J. Kopeček, P. Kopečková, Adv. Drug Deliv. Rev. 2010, 62, 122.
| Crossref | GoogleScholarGoogle Scholar |
[9] M. L. Graham, Adv. Drug Deliv. Rev. 2003, 55, 1293.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXnt1yqsbk%3D&md5=267cfd54583fbb9a1d1e2658953f921fCAS |
[10] Y. Levy, M. S. Hershfield, C. Fernandez-Mejia, S. H. Polmar, D. Scudiery, M. Berger, R. U. Sorensen, J. Pediatr. 1988, 113, 312.
| Crossref | GoogleScholarGoogle Scholar | 1:STN:280:DyaL1c3os1alsg%3D%3D&md5=1e90a6060f0f92a9dce41f94b5007cecCAS |
[11] P. Bailon, A. Palleroni, C. A. Schaffer, C. L. Spence, W.-J. Fung, J. E. Porter, G. K. Ehrlich, W. Pan, Z.-X. Xu, M. W. Modi, A. Farid, W. Berthold, M. Graves, Bioconjug. Chem. 2001, 12, 195.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXhtFGlur8%3D&md5=7ed7b20d006de367e02d4bf24d50e95cCAS |
[12] Y.-S. Wang, S. Youngster, M. Grace, J. Bausch, R. Bordens, D. F. Wyss, Adv. Drug Deliv. Rev. 2002, 54, 547.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XktFKhsr8%3D&md5=c1c04ae25a260fba971754dd47188640CAS |
[13] P. J. Trainer, W. M. Drake, L. Katznelson, P. U. Freda, V. Herman-Bonert, A. J. van der Lely, E. V. Dimaraki, P. M. Stewart, K. E. Friend, M. L. Vance, G. M. Besser, M. O. Thorner, C. Parkinson, A. Klibanski, J. S. Powell, A. L. Barkan, M. C. Sheppard, M. Maldonado, D. R. Rose, D. R. Clemmons, G. Johannsson, B.-Å. Bengt-Åke Bengtsson, S. Stavrou, D. L. Kleinberg, D. M. Cook, L. S. Phillips, M. Bidlingmaier, C. J. Strasburger, S. Hackett, K. Zib, W. F. Bennett, R. J. Davis, J. A. Scarlett, New Engl. J. Med. 2000, 342, 1171.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXjtVOkur4%3D&md5=990392c7e7ce9f951187c4e5cddbe2c6CAS |
[14] R. Hoogenboom, Angew. Chem. Int. Ed. 2009, 48, 7978.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXht1Kju7%2FP&md5=c67d933e984087b73c2ddb1a558df256CAS |
[15] P. Goddard, L. E. Hutchinson, J. Brown, L. J. Brookman, J. Control. Release 1989, 10, 5.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXkt1ensQ%3D%3D&md5=0f733fb03ad089ee90c82a4abae2535cCAS |
[16] M. Miyamoto, K. Naka, M. Shiozaki, Y. Chujo, T. Saegusa, Macromolecules 1990, 23, 3201.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXktVams7c%3D&md5=e482f94543caeb121424ea4227919002CAS |
[17] C. Weber, T. Neuwirth, K. Kempe, B. Ozkahraman, E. Tamahkar, H. Mert, C. R. Becer, U. S. Schubert, Macromolecules 2012, 45, 20.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhs1SmtbjL&md5=dca3c3e7af98f70e0b3bcc3d70610ceaCAS |
[18] R. M. Paulus, C. R. Becer, R. Hoogenboorn, U. S. Schubert, Macromol. Chem. Phys. 2008, 209, 794.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXlvFeksLg%3D&md5=5a74fddf3a79357cbcfca8b581db9a74CAS |
[19] K. V. Bernaerts, F. E. Du Prez, Prog. Polym. Sci. 2006, 31, 671.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtFSnt77O&md5=9544263798a994088d6b18b7a318c37dCAS |
[20] M. A. Tasdelen, M. U. Kahveci, Y. Yagci, Prog. Polym. Sci. 2011, 36, 455.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtlKltbc%3D&md5=18397357422cead59c6dac49c10cee8fCAS |
[21] C. R. Becer, R. M. Paulus, S. Hoppener, R. Hoogenboom, C. A. Fustin, J. F. O. Gohy, U. S. Schubert, Macromolecules 2008, 41, 5210.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXnvVKlu78%3D&md5=4de6a0cfe45e15e9b44a04279a35beadCAS |
[22] V. Percec, T. Guliashvili, J. S. Ladislaw, A. Wistrand, A. Stjerndahl, M. J. Sienkowska, M. J. Monteiro, S. Sahoo, J. Am. Chem. Soc. 2006, 128, 14156.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtVaqs7jK&md5=2c1d0794956b41daeb48d5821bafd0faCAS |
[23] C. R. Becer, R. Hoogenboom, D. Fournier, U. S. Schubert, Macromol. Rapid Commun. 2007, 28, 1161.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXmtlKnurc%3D&md5=d619521aec6da02d9cceab7319d98555CAS |
[24] M. E. Levere, I. Willoughby, S. O'Donohue, A. de Cuendias, A. J. Grice, C. Fidge, C. R. Becer, D. M. Haddleton, Polym. Chem. 2010, 1, 1086.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtl2ms7fJ&md5=f67b8b4d30267a4f419913f0a723b1e0CAS |
[25] C. R. Becer, C. Haensch, S. Hoeppener, U. S. Schubert, Small 2007, 3, 220.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhvFWhsbs%3D&md5=afc58c046fde4cd3156f3eeb18e1d3e4CAS |
[26] M. E. Levere, I. Willoughby, S. O'Donohue, P. M. Wright, A. J. Grice, C. Fidge, C. R. Becer, D. M. Haddleton, J. Polym. Sci. A Polym. Chem. 2011, 49, 1753.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXjt1Ghs7c%3D&md5=0b4a326d923de8dcb7de403d25cc3f49CAS |
[27] N. H. Nguyen, M. E. Levere, V. Percec, J. Polym. Sci. A Polym. Chem. 2012, 50, 860.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhsFWqtLvI&md5=b8f607b62f6829388cbfc74f5cf6e71aCAS |
[28] K. Kempe, C. R. Becer, U. S. Schubert, Macromolecules 2011, 44, 5825.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXovVOju7k%3D&md5=c731e3b36325471e671d6a2764db6d1dCAS |
[29] C. Boyer, A. Derveaux, P. B. Zetterlund, M. R. Whittaker, Polym. Chem. 2012, 3, 117.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhsFGjsb3E&md5=da942f11992ecd94035a35d9e716dcd3CAS |