Disperse red 1 end capped oligoesters. Synthesis by noncatalyzed ring opening oligomerization and structural characterization |
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| Authors: | Cristian Peptu Valeria Harabagiu Bogdan C Simionescu Grazyna Adamus Marek Kowalczuk Jean‐Michel Nunzi |
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| Institution: | 1. Institute of Chemistry and Environmental Protection, “Jan Dlugosz” University of Czestochowa, 13/15 Armii Krajowej Av., 42‐200 Czestochowa, Poland;2. “Petru Poni” Institute of Macromolecular Chemistry, Aleea Grigore Ghica Voda 41A, 700487 Iasi, Romania;3. “Gh. Asachi” Technical University, Department of Natural and Synthetic Polymers, 700050 Iasi, Romania;4. Polish Academy of Sciences, Centre of Polymer and Carbon Materials, 34 M. Sklodowskiej‐Curie, 41‐819 Zabrze, Poland;5. Queen's University, Department of Physics and Chemistry, 90 Bader Lane, Kingston K7L 3N6, Ontario, Canada |
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| Abstract: | The synthesis of novel azofunctional oligoesters through bulk ring opening of ε‐caprolactone and D ,L ‐lactide (LA) at 100 and 130 °C, respectively, mediated by N‐ethyl‐N‐(2‐hydroxyethyl)‐4‐(4‐nitrophenylazo)aniline (Disperse Red 1) (DR1) is described. The synthetic procedure allows “clean” products because no catalysts were used in the reaction. Moreover, DR1 moiety is showed for the first time to promote the ring opening of cyclic esters. The molecular structure of the obtained oligoesters was established by NMR spectroscopy, MALDI ToF MS and electrospray ionization mass spectrometry (ESI MS). ESI‐MS/MS fragmentation experiments were used to demonstrate the nature of the chain end groups (hydroxyl and DR1). Intermolecular transesterification reactions were proved by mass spectrometry studies at least in the case of LA oligomerization. © 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 534–547, 2009 |
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| Keywords: | azofunctional oligoesters disperse red 1 mass spectrometry oligocaprolactone oligolactide polyesters ring opening oligomerization ring opening polymerization |
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