Copolymers of 2-hydroxyethylacrylate and 2-methoxyethyl acrylate by nitroxide mediated polymerization: Kinetics, SEC-ESI-MS analysis and thermoresponsive properties

Hoogenboom, R., Zorn, A. M., Keul, H., Barner-Kowollik, C., & Moeller, M. (2012) Copolymers of 2-hydroxyethylacrylate and 2-methoxyethyl acrylate by nitroxide mediated polymerization: Kinetics, SEC-ESI-MS analysis and thermoresponsive properties. Polymer Chemistry, 3(2).

View at publisher

Abstract

The nitroxide mediated copolymerization of 2-hydroxyethyl acrylate (HEA) and 2-methoxyethyl acrylate (MEA) is reported. The copolymerization kinetics followed the persistent radical model and revealed the formation of well-defined ideal random copolymers (r HEA = 0.93 ± 0.09; r MEA = 0.95 ± 0.09). SEC-ESI-MS proved the presence of both the initiation fragment and SG1 as chain ends of the polymers. The cloud point temperature of the copolymers increased from 5 °C and 60 °C with increasing HEA content from 0% to 70% and they are discussed in relation to both monomer and end-group structure. © 2012 The Royal Society of Chemistry.

Impact and interest:

25 citations in Scopus
27 citations in Web of Science®
Search Google Scholar™

Citation counts are sourced monthly from Scopus and Web of Science® citation databases.

These databases contain citations from different subsets of available publications and different time periods and thus the citation count from each is usually different. Some works are not in either database and no count is displayed. Scopus includes citations from articles published in 1996 onwards, and Web of Science® generally from 1980 onwards.

Citations counts from the Google Scholar™ indexing service can be viewed at the linked Google Scholar™ search.

ID Code: 99313
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :20
Export Date: 5 September 2016
Correspondence Address: Hoogenboom, R.; Supramolecular Chemistry Group, Department of Organic Chemistry, Ghent University, Krijgslaan 281-S4, 9000 Ghent, Belgium; email: richard.hoogenboom@ugent.be
References: Gil, E.S., Hudson, S.M., (2004) Prog. Polym. Sci., 29, p. 1173; De Las, H.A.C., Pennadam, S., Alexander, C., (2004) Chem. Soc. Rev., 34, p. 275; Schmaljohann, D., (2006) Adv. Drug Delivery Rev., 58, p. 1655; Yoshida, R., Sakai, K., Okano, T., Sakurai, Y., (1993) Adv. Drug Delivery Rev., 11, p. 85; Klouda, L., Mikos, A.G., (2008) Eur. J. Pharm. Biopharm., 68, p. 34; Vertommen, M.A.M.E., Cornelissen, H.-J.L., Dietz, C.H.J.T., Hoogenboom, R., Kemmere, M.F., Keurentjes, J.T.F., (2008) J. Membr. Sci., 322, p. 243; Costioli, M.D., Fisch, I., Garret-Flaudy, F., Hilbrig, F., Freitag, R., (2003) Biotechnol. Bioeng., 81, p. 535; Kikuchi, A., Okano, T., (2002) Prog. Polym. Sci., 27, p. 1165; Lavigueur, C., Gonzalez-Garcia, J., Hendriks, L., Hoogenboom, R., Cornelissen, J.J.L.M., Nolte, R.J.M., (2011) Polym. Chem., 2, p. 333; Okano, T., Yamada, N., Okuhara, M., Sakai, H., Sakurai, Y., (1995) Biomaterials, 16, p. 297; Wischerhoff, E., Uhlig, K., Lankenau, A., Börner, H.G., Laschewsky, A., Duschl, C., Lutz, J.-F., (2008) Angew. Chem., Int. Ed., 47, p. 5666; Weinhart, M., Becherer, T., Haag, R., (2011) Chem. Commun., 47, p. 1553; Uchiyama, S., Kawai, N., De Silva, A.P., Iwai, K., (2004) J. Am. Chem. Soc., 126, p. 3032; Pietsch, C., Hoogenboom, R., Schubert, U.S., (2009) Angew. Chem., Int. Ed., 48, p. 5653; Jochum, F.D., Theato, P., (2010) Chem. Commun., 46, p. 6717; Pietsch, C., Schubert, U.S., Hoogenboom, R., (2011) Chem. Commun., 47, p. 8750; Taylor, L.D., Cerankowski, L.D., (1975) J. Polym. Sci., Polym. Chem. Ed., 13, p. 2551; Schild, H.G., (1992) Prog. Polym. Sci., 17, p. 163; Aoshima, S., Kanaoka, S., (2008) Adv. Polym. Sci., 210, p. 169; Lutz, J.-F., Akdemir, O., Hoth, A., (2006) J. Am. Chem. Soc., 128, p. 13046; Lutz, J.-F., (2008) J. Polym. Sci., Part A: Polym. Chem., 46, p. 3459; Becer, C.R., Hahn, S., Fijten, M.W.M., Thijs, H.M.L., Hoogenboom, R., Schubert, U.S., (2008) J. Polym. Sci., Part A: Polym. Chem., 46, p. 7138; Roth, P.J., Jochum, F.D., Forst, F.R., Zentel, R., Theato, P., (2010) Macromolecules, 43, p. 4638; Lutz, J.-F., (2011) Adv. Mater., 23, p. 2237; Hoogenboom, R., (2009) Angew. Chem., Int. Ed., 48, p. 7978; Diehl, C., Schlaad, H., (2009) Macromol. Biosci., 9, p. 157; Diab, C., Akiyama, Y., Kataoka, K., Winnik, F.M., (2004) Macromolecules, 37, p. 2556; Hoogenboom, R., Thijs, H.M.L., Jochems, M.J.H.C., Van Lankvelt, B.M., Fijten, M.W.M., Schubert, U.S., (2008) Chem. Commun., p. 5758; Kempe, K., Neuwirth, T., Czaplewska, J., Gottschaldt, M., Hoogenboom, R., Schubert, U.S., (2011) Polym. Chem., 2, p. 1737; Seifert, L.M., Green, R.T., (1985) J. Biomed. Mater. Res., 19, p. 1043; Okano, T., Aoyagi, T., Kataoka, K., Abe, K., Sakurai, Y., Shimadada, M., Shinohara, I., (1986) J. Biomed. Mater. Res., 20, p. 919; Weaver, J.V.M., Bannister, I., Robinson, K.L., Bories-Azeau, X., Armes, S.P., Smallridge, M., McKenna, P., (2004) Macromolecules, 37, p. 2395; Khutoryanskaya, A.V., Mayeva, Z.A., Mun, G.A., Khutoryanskiy, V.V., (2008) Biomacromolecules, 9, p. 3353; Chan, Y., Wong, T., Byrne, F., Kavallaris, M., Bulmus, V., (2008) Biomacromolecules, 9, p. 1826; Arun, A., Reddy, B.S.R., (2005) Biomaterials, 26, p. 1185; Lück, M., Paulke, B.-R., Schröder, W., Blunk, T., Müller, R.H., (1998) J. Biomed. Mater. Res., 39, p. 478; McAllister, K., Sazani, P., Adam, M., Cho, M.J., Rubinstein, M., Samulski, R.J., Desimone, J.M., (2002) J. Am. Chem. Soc., 124, p. 15198; Martinez-Ramos, C., Lainez, S., Sancho, F., Esparza, M.A.G., Planells-Cases, R., Verdugo, J.M.G., Ribelles, J.L.G., Soria, J.M., (2008) Tissue Eng. A, 14, p. 1365; Valles Lluch, A., Campillo Frenandez, A., Gallego Ferrer, G., Monleon Pradas, M., (2009) J. Biomed. Mater. Res., Part B, 90, p. 182; Mun, G.A., Nurkeeva, Z.S., Akhmetkalieva, G.T., Shmakov, S.N., Khutoyanskiy, V.V., Lee, S.C., Park, K., (2006) J. Polym. Sci., Part B: Polym. Phys., 44, p. 195; Mun, G.A., Nurkeeva, Z.S., Beissegul, A.B., Dubolazov, A.V., Urkimbaeva, P.I., Park, K., Khutoyanskiy, V.V., (2007) Macromol. Chem. Phys., 208, p. 979; Khutoryanskaya, A.V., Mayeva, Z.A., Mun, G.A., Khutoryanskiy, V.V., (2008) Biomacromolecules, 9, p. 3353; Wang, J.S., Matyjaszewski, K., (1995) Macromolecules, 28, p. 7901; Kamigaito, M., Ando, T., Sawamoto, M., (2001) Chem. Rev., 101, p. 3689; Chiefari, J., Chong, Y.K., Ercole, F., Krstina, J., Jeffery, J., Le, T.P.T., Mayadunne, R.T., Thang, S.H., (1998) Macromolecules, 31, p. 5559; Barner-Kowollik, C., Davis, T.P., Heuts, J.P.A., Stenzel, M.H., Vana, P., Whittaker, M., (2003) J. Polym. Sci., Part A: Polym. Chem., 41, p. 365; Veregin, R.P.N., Georges, M.K., Hamer, G.K., Kazmaier, P.M., (1995) Macromolecules, 28, p. 4391; Fukuda, T., Terauchi, T., Goto, A., Ohno, K., Tsujii, Y., Miyamoto, T., Kobatake, S., Yamada, B., (1996) Macromolecules, 29, p. 6393; Hawker, C.J., Bosman, A.W., Harth, E., (2001) Chem. Rev., 101, p. 3661; Lai, J.T., Filla, D., Shea, R., (2002) Macromolecules, 35, p. 6754; Lizotte, J.R., Long, T.E., (2004) Macromol. Chem. Phys., 205, p. 692; Wang, Y., Armitage, B.A., Berry, G.C., (2005) Macromolecules, 38, p. 5846; Bian, K., Cunningham, M.F., (2005) Macromolecules, 38, p. 695; Clement, B., Trimaille, T., Alluin, O., Gigmes, D., Mabrouk, K., Feron, F., Decherchi, P., Bertin, D., (2009) Biomacromolecules, 10, p. 1436; Hoogenboom, R., Popescu, D., Steinhauer, W., Keul, H., Moeller, M., (2009) Macromol. Rapid Commun., 30, p. 2042; Popescu, D., Hoogenboom, R., Keul, H., Moeller, M., (2010) Polym. Chem., 1, p. 878; Steinhauer, W., Hoogenboom, R., Keul, H., Moeller, M., (2010) Macromolecules, 43, p. 7041; Le Mercier, C., Acerbis, S., Bertin, D., Chauvin, F., Gigmes, D., Guerret, O., Lansalot, M., Tordo, P., (2002) Macromol. Symp., 182, p. 225; Nicolas, J., Charleux, B., Guerret, O., Magnet, S., (2004) Macromolecules, 37, p. 4453; Nicolas, J., Dire, C., Mueller, L., Belleney, J., Charleux, B., Marque, S.R.A., Bertin, D., Couvreur, L., (2006) Macromolecules, 39, p. 8274; Nicolas, J., Charleux, B., Guerret, O., Magnet, S., (2004) Angew. Chem., Int. Ed., 43, p. 6186; Lacroix-Desmazes, P., Lutz, J.-F., Chauvin, F., Severac, R., Boutevin, B., (2001) Macromolecules, 34, p. 8866; Becer, C.R., Paulus, R.M., Hoogenboom, R., Schubert, U.S., (2006) J. Polym. Sci., Part A: Polym. Chem., 44, p. 6202; Grimaldi, S., Finet, J.-P., Le Moigne, F., Zeghdaoui, A., Tordo, P., Benoit, D., Fontanille, M., Gnanou, Y., (2000) Macromolecules, 33, p. 1141; Eggenhuisen, T.M., Becer, C.R., Fijten, M.W.M., Eckardt, R., Hoogenboom, R., Schubert, U.S., (2008) Macromolecules, 41, p. 5132; Gründling, T., Guilhaus, M., Barner-Kowollik, C., (2008) Anal. Chem., 80, p. 6915; Barner-Kowollik, C., Davis, T.P., Stenzel, M.H., (2004) Polymer, 45, p. 7791; Delaittre, G., Rieger, J., Charleux, B., (2011) Macromolecules, 44, p. 417; Fischer, H., (1997) Macromolecules, 30, pp. 5666-5672; Lutz, J.-F., Lacroix-Desmazes, P., Boutevin, B., (2001) Macromol. Rapid Commun., 22, p. 189; Junkers, T., Barner-Kowollik, C., (2008) J. Polym. Sci., Part A: Polym. Chem., 46, p. 7585
Keywords: 2-hydroxyethylacrylate, Chain-ends, Cloud point temperature, End groups, Nitroxide mediated polymerization, Nitroxides, Random copolymer, Thermo-responsive, Acrylics, Copolymerization, Polymers, Copolymers
DOI: 10.1039/c1py00344e
ISSN: 17599954
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > Institutes > Institute for Future Environments
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 22 Sep 2016 04:50
Last Modified: 04 Oct 2016 05:08

Export: EndNote | Dublin Core | BibTeX

Repository Staff Only: item control page