Linear polyurethanes with imidazoquinazoline rings: preparation and properties evaluation

Abstract

Abstract: In this work, research concerning the synthesis and properties of linear polyurethanes (PUs) with the imidazoquinazoline rings was represented. Reaction conditions of 2,6-bis(2-hydroxyethyl)-1-phenylimida-zo[1,5-c]quinazoline-3,5-dione (BHPIQ) with 1,6-hexamethylene diisocyanate were determined and optimized. These conditions are adapted to reaction of BHPIQ with 4,4′-diphenylmethane diisocyanate and 2,4-toluene diisocyanate. New PUs with imidazoquinazoline rings were characterized by spectral methods ( 1 H-NMR and IR spectroscopies), which confirm their structures. Their molar masses and dispersity index were measured by size exclusion chromatography method. The wide-angle X-ray scattering and differential scanning calorimetry (DSC) studies have shown that all PUs based on BHPIQ are amorphous. Moreover, thermal properties of PUs were investigated by thermogravimetry analysis, standard DSC, and temperature-modulated DSC methods. During thermogravimetric measurements, the exhaust gases were analyzed by FTIR method. Incorporation of imidazoquinazoline ring into the PU chains escalates their glass transition temperature; thus, their heat resistance was enhanced. Furthermore, their degradation rate and the amount of released degradation products were reduced. The investigated properties of the obtained PUs with imidazoquinazoline rings were compared with those ones of suitable PUs based on 1,4-butanediol. Graphical abstract: Linear polyurethanes were obtained in reaction of 1-phenyl-2,6-bis(2-hydroxyethylimidazo[1,5-c]quinazoline-3,5-dione with hexamethylene 1,6-diisocyanate, 4,4′-diphenylmethane diisocyanate and toluene 2,4-diisocyanate. Their composition and structure were confirmed. The phase contents and thermal properties were investigated[Figure not available: see fulltext.]. © 2019, The Author(s).