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Synthesis of new Biginelli polycondensates: renewable materials with tunable high glass transition temperatures

Windbiel, Julian T. 1; Meier, Michael A. R. 1,2
1 Laboratorium für Applikationen der Synchrotronstrahlung (LAS), Karlsruher Institut für Technologie (KIT)
2 Institut für Organische Chemie (IOC), Karlsruher Institut für Technologie (KIT)


The Biginelli reaction was applied as a simple one‐pot multicomponent polycondensation approach to efficiently synthesize a set of 15 new and fully renewable poly(3,4‐dihydropyrimidin‐2(1H)‐one)s. One of six bis‐acetoacetates or three bis‐acetoacetamides, terephthalic aldehyde and (methyl‐)urea were used as renewable starting materials in various combinations, hence significantly expanding the known set of monomers as well as polymer structures. The bis‐acetoacetates and bis‐acetoacetamides with different spacer lengths were synthesized in yields of up to 99% in a one‐step process. Thermal analysis of the obtained set of polymers revealed high glass transition temperatures (T$_{g}$) ranging from 160 to 308 °C. The T$_{g}$ was tunable in small steps of 10 °C by simple variation of bis‐acetoacetate or bis‐acetoacetamide monomers as well as the choice of (methyl‐)urea. The poly(3,4‐dihydropyrimidin‐2(1H)‐one)s showed good thermal stability with T$_{d5%}$ values well above the respective high T$_{g}$ values.

Verlagsausgabe §
DOI: 10.5445/IR/1000124422
Veröffentlicht am 13.10.2020
DOI: 10.1002/pi.6106
Zitationen: 4
Web of Science
Zitationen: 3
Zitationen: 4
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Biologische und Chemische Systeme (IBCS)
Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsmonat/-jahr 05.2021
Sprache Englisch
Identifikator ISSN: 0959-8103, 1097-0126
KITopen-ID: 1000124422
HGF-Programm 47.01.01 (POF III, LK 01) Biol.Netzwerke u.Synth.Regulat. ITG+ITC
Weitere HGF-Programme 43.33.11 (POF IV, LK 01) Adaptive and Bioinstructive Materials Systems
Erschienen in Polymer international
Verlag John Wiley and Sons
Band 70
Heft 5
Seiten 506-513
Vorab online veröffentlicht am 14.09.2020
Nachgewiesen in Web of Science
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