An investigation of novel biodegradable flexible copolyester derived from bio-based isosorbide: Synthesis and characterization of poly(butylene-co-isosorbide sebacate)

Abstract

A series of fully bio-based poly(butylene-co-isosorbide sebacate) (PBISe) copolyesters are synthesized from sebacic acid (Se), 1,4-butanediol (BDO), and isosorbide (IS) via a two-step melt polycondensation method. The synthesized PBISe copolyesters are characterized using various techniques, including 1H NMR spectroscopy; GPC; FT-IR spectroscopy; HR-XRD; DSC; TGA; transparency, tensile, and tear strength testing; and rheological property analysis. The Mw and Mn values of the PBISe copolyesters are 126,000–148,000 and 50,000–63,500, respectively. The introduction of the rigid, bulky, and asymmetric IS unit disrupts the regularity and mobility of the polymer chain, resulting in a nearly linear reduction of the melting temperature, enthalpy, and crystallinity, from 66 to 42 °C, 81 to 37 J/g, and 41.4 to 19.0%, respectively, with an increase in the IS content from 0 to 30 mol% relative to the total diol concentration. The reduction of crystallinity without the formation of new crystal planes with the poly(butylene sebacate (PBSe) copolyester containing 30 mol% IS resulted in improved transparency (73.8% transmittance at 600 nm). Additionally, the PBISe copolyesters exhibit Tonset and Tmax in excess of 405 °C and 425 °C, respectively, as well as shear-thinning and viscous melt-flow behaviors, making them suitable for melt processing. The tensile strength and elongation at break of the hot-pressed films of the IS-added PBISe copolyesters with ≤16% content are 31.6–36.3 MPa and 639.2–809.9%, respectively. The developed PBISe copolyesters have great potential as bio-based, biodegradable, and flexible materials for packaging and coating applications with low processing temperatures.