Thermally cleavable Imine Base / Isocyanate Adducts and Oligomers suitable as Initiators for Radical Homo- and Copolymerization
| Autor: | Polenz, Ingmar, Laue, Andreas, Uhrin, Tamas, Rueffer, Tobias, Lang, Heinrich, Schmidt, Friedrich, Spange, Stefan |
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| Jazyk: | angličtina |
| Rok vydání: | 2014 |
| Předmět: | |
| Zdroj: | Polymer Chemistry, 2014, 1-3, 1759-9962 |
| Druh dokumentu: | Článek |
| ISSN: | 1759-9962 |
| DOI: | 10.1039/C4PY01002G |
| Popis: | The addition of isocyanates to C=N double bonds of imines gives triazindione heterocycle structures; their thermal properties are reported. Mono-isocyanates were used to form 2:1 adducts with the imine bases 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) and 2-tert-butyl-1,1,3,3-tetramethylguanidine (tBuTMG). A 2:1 stoichiometry of the adducts was proven by NMR and IR spectroscopy, and single crystal X-Ray diffraction; certain cleavage temperatures (70 and 160 °C) were measured. Thermal analysis (TG-MS) of adducts indicates the release of free isocyanate during adduct cleavage. Furthermore, a new class of step-growth oligomers (MN = 750–7,000 g∙mol–1) composed of multi-functional isocyanates and these imine bases was introduced. Their systematic spectroscopic and thermal analysis is shown revealing the similarity in their chemical properties to the 2:1 adducts. Radical homo- and copolymerization of acrylates is initiated by the meta-stable adducts and oligomers of this work; the generation of novel telomeric block-copolymer architectures composed of polyacrylate and oligourea building blocks is demonstrated. Dieser Beitrag ist aufgrund einer (DFG-geförderten) Allianz- bzw. Nationallizenz frei zugänglich. |
| Databáze: | Networked Digital Library of Theses & Dissertations |
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