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Fully Renewable Non-Isocyanate Polyurethanes via the Lossen Rearrangement [in press]

Filippi, Luca; Meier, Michael A. R.

Abstract:
In this work, a straightforward and efficient synthesis approach to renewable non‐isocyanate polyurethanes (NIPUs) is described. For this purpose, suitable and renewable carbamate monomers, possessing two double bonds, are synthesized from hydroxamic fatty acid derivatives via the Lossen rearrangement in a one‐step synthesis, and sustainable dithiols are synthesized from dialkenes derived from renewable feedstock (i.e., limonene and 1,4‐cyclohexadiene). Subsequently, the comonomers are polymerized with the highly efficient thiol–ene reaction to produce NIPUs with M$_{n}$ values up to 26 kg mol$^{−1}$ bearing thioether linkages. The main side product of the Lossen rearrangement, a symmetric urea, can also be polymerized in the same fashion. Important in the view of sustainability, the monomer mixture can also be used directly, without separation. The obtained polymers are characterized by NMR, attenuated total reflection‐infrared spectroscopy, differential scanning calorimetry, and size exclusion chromatography.

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Verlagsausgabe §
DOI: 10.5445/IR/1000125244
Veröffentlicht am 23.10.2020
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Institut für Biologische und Chemische Systeme (IBCS)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2020
Sprache Englisch
Identifikator ISSN: 0173-2803, 1022-1336, 1521-3927
KITopen-ID: 1000125244
HGF-Programm 47.01.01 (POF III, LK 01)
Biol.Netzwerke u.Synth.Regulat. ITG+ITC
Erschienen in Macromolecular rapid communications
Seiten Art.-Nr.: 2000440
Vorab online veröffentlicht am 16.09.2020
Nachgewiesen in Scopus
Web of Science
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