Abstract
Environmental and health concerns force the search for sustainable super engineering plastics (SEPs) that utilise bio-derived cyclic monomers, e.g. isosorbide instead of restricted petrochemicals. However, previously reported bio-derived thermosets or thermoplastics rarely offer thermal/mechanical properties, scalability, or recycling that match those of petrochemical SEPs. Here we use a phase transfer catalyst to synthesise an isosorbide-based polymer with a high molecular weight >100 kg mol−1, which is reproducible at a 1-kg-scale production. It is transparent and solvent/melt-processible for recycling, with a glass transition temperature of 212 °C, a tensile strength of 78 MPa, and a thermal expansion coefficient of 23.8 ppm K−1. Such a performance combination has not been reported before for bio-based thermoplastics, petrochemical SEPs, or thermosets. Interestingly, quantum chemical simulations show the alicyclic bicyclic ring structure of isosorbide imposes stronger geometric restraint to polymer chain than the aromatic group of bisphenol-A.
Highlights
Environmental and health concerns force the search for sustainable super engineering plastics (SEPs) that utilise bio-derived cyclic monomers, e.g. isosorbide instead of restricted petrochemicals
A typical synthesis route of aromatic Poly (arylene ether)s (PAEs) is based on nucleophilic aromatic substitution (SNAr)
BPA forms a complex consisting of K+ and nucleophile [phenoxide]−, which displaces the halogen of DFPS59
Summary
Environmental and health concerns force the search for sustainable super engineering plastics (SEPs) that utilise bio-derived cyclic monomers, e.g. isosorbide instead of restricted petrochemicals. Previously reported bio-derived thermosets or thermoplastics rarely offer thermal/mechanical properties, scalability, or recycling that match those of petrochemical SEPs. Here we use a phase transfer catalyst to synthesise an isosorbide-based polymer with a high molecular weight >100 kg mol−1, which is reproducible at a 1-kg-scale production. The many environmental concerns associated with plastic’s constituents have led to the search for sustainable highperformance thermoplastics that are entirely or partially derived from bio-derived feedstocks, instead of petrochemicals, and match those that they replace in terms of thermomechanical properties[1] Aromatic petrochemicals such as bisphenol-A (BPA), biphenols, styrenes, and terephthalates are key monomers in determining the thermal and mechanical properties of EPs and SEPs; many of them are toxic and pollute the environment. A French agricultural company recently has achieved the world’s highest annual high-purity ISB production of 20,000 tons
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