Synthesis of a macromonomer library from high-temperature acrylate polymerization

Zorn, A. M., Junkers, T., & Barner-Kowollik, C. (2009) Synthesis of a macromonomer library from high-temperature acrylate polymerization. Macromolecular Rapid Communications, 30(23).

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The auto-initiated high temperature acrylate polymerization represents a versatile route for the synthesis of macromonomer building blocks. Various macromonomers were synthesized via this route based on methyl, ethyl, n-butyl, t-butyl, 2-ethylhexyl, isobornyl and 2-[[(butylamino) carbonyl]oxy]ethyl acrylate. The synthesis requires a temperature of 140°C and is carried out in a 5 wt.-% solution of hexyl acetate. The macromonomer library is fully characterized via electrospray ionization mass spectrometry (ESI-MS). The amount of macromonomers containing the geminal double bond lies in between 82 and 95%, depending on the monomer type. The achievable molecular weight of the macromonomers is located between 800 and 2 000 g·mol-1 with a polydispersity of close to 1.6. In addition, it is demonstrated that radical initiators are useful add-ons (to circumvent the inhibition time observed during initiator-free synthesis) without interfering in the actual polymerization as no initiator-fragment containing products are identified via high resolution mass spectrometry. (Figure Presented). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

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24 citations in Web of Science®
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ID Code: 99230
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :23
Export Date: 5 September 2016
Correspondence Address: Junkers, T.; Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstr. 18, 76128 Karlsruhe, Germany; email:
References: Chiefari, J., Chong, Y.K., Ercole, F., Krstina, J., Jeffery, J., Le, T.P.T., Mayadunne, R.T.A., Thang, S.H., (1998) Macromolecules, 31, p. 5559; Moad, G., Barner-Kowollik, C., The Mechanism and Kinetics of the RAFT Process (2008) Handbook of RAFT Polymerization, , C. Barner-Kowollik, Ed., Wiley-VCH, Weinheim; Matyjaszewski, K., Xia, J., (2001) Chem. Rev., 101, p. 2921; Hawker, C.J., Bosman, A.W., Harth, E., (2001) Chem. Rev., 301, p. 3661; Barner-Kowollik, C., Inglis, A.J., (2009) Macromol. Chem. Phys., 201, p. 987; Chiefari, J., Jeffery, J., Mayadunne, R.T.A., Moad, G., Rizzardo, E., Thang, S.H., (1999) Macromolecules, 32, p. 7700; (1998), US 98/47927Junkers, T., Barner-Kowollik, C., (2008) J. Polym. Sci. Polym. Chem., 46, p. 7585; Willemse, R.X.E., Van Herk, A.M., Panchenko, E., Junkers, T., Buback, M., (2005) Macromolecules, 38, p. 5098; Nikitin, A.N., Hutchinson, R.A., Buback, M., Hesse, P., (2007) Macromolecules, 40, p. 8631; Barner-Kowollik, C., Davis, T.P., Stenzel, M.H., (2004) Polymer, 45, pp. 7791-7805; Junkers, T., Bennet, F., Koo, S.P.S., Barner-Kowollik, C., (2008) J. Polym. Sci. Polym. Chem., 46, p. 3433; Hadjichristidis, N., Pitsikalis, M., Iatrou, H., Pispas, S., (2003) Macromol. Rapid Commun., 4, p. 979; Li, D., Grady, M.C., Hutchinson, R.A., (2005) Ind. Eng. Chem. Res., 44, p. 2506; Quan, C., Soroush, M., Grady, M.C., Hansen, J.E., Simonsick, W.J., (2005) Macromolecules, 38, p. 7619; Grady, M.C., Simonsick, W.J., Hutchinson, R.A., (2002) Macromol. Symp., 182, p. 149; Junkers, T., Barner-Kowollik, C., (2009) Macromol. Theory Simul., , DOI:10.1002/mats.200900025; Strazielle, C., Benoit, H., Vogl, O., (1978) Eur. Polym. J., 14, p. 331; Penzel, E., Götz, N., (1990) Angew. Makromol. Chem., 178, p. 191; Dervaux, B., Junkers, T., Schneider-Baumann, M., Du Prez, F.E., Barner-Kowollik, C., (2009) J. Polym. Sci., Part A, , DOI:10.1002/pola.23706; Gruendling, T., Junkers, T., Guilhaus, M., Barner-Kowollik, C., (2009) Macromol. Chem. Phys., , DOI:10.1002/macp.200900323; Van Hook, J.P., Tobolsky, A.V., (1958) J. Am. Chem. Soc., 80, p. 779; Overberger, C.G., Biletch, H., Finestone, A.B., Lilker, J., Herbert, J., (1953) J. Am. Chem. Soc., 75, p. 2078; Zorn, A.-M., Diploma thesis (2009) Karlsruhe University, Karlsruhe; Junkers, T., (2008) Aust. J. Chem., 61, p. 646; Koo, S.P.S., Junkers, T., Barner-Kowollik, C., (2009) Macromolecules, 42, p. 62; Junkers, T., Koo, S.P.S., Davis, T.P., Stenzel, M.H., Barner-Kowollik, C., (2007) Macromolecules, 40, p. 8906; Müller, M., (2005) Dissertation, , Göttingen University, Göttingen
Keywords: β-scission, Acrylates, Macromonomers, Mass spectrometry, Radical polymerization, Self-initiated polymerization, [carbonyl, Building blockes, Double bonds, Electrospray ionization mass spectrometry, Ethyl acrylates, Hexyl acetate, High resolution mass spectrometry, High temperature, In-between, Inhibition time, Macromonomer, Monomer types, Radical initiators, Atom transfer radical polymerization, Electrospray ionization, Mass spectrometers, Monomers, Polydispersity, Polymers, Salts, Synthesis (chemical), Free radical polymerization
DOI: 10.1002/marc.200900536
ISSN: 10221336
Divisions: Current > Institutes > Institute for Future Environments
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 22 Sep 2016 04:50
Last Modified: 28 Jun 2017 15:01

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