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article
Semi-Crystalline and Amorphous Polyesters Derived from Biobased Tri-Aromatic Dicarboxylates and Containing Cleavable Acylhydrazone Units for Short-Loop Chemical Recycling
Abstract
Recycling polymers by site-specific scission into short-chain oligomers/polymers, followed by recoupling these to form the original polymer presents an energetically more favorable shorter-loop chemical recycling in comparison to recycling into monomers. Here, we present the synthesis and polymerization of triaromatic diesters to prepare polyesters with acylhydrazone units as weak structural links. Two diester monomers were prepared by combining methyl 5-chloromethyl-2-furoate, obtained from 5-chloromethylfurfural (CMF), with potentially biobased hydroquinone and resorcinol, respectively. The two diesters having a central phenyl ring flanked by two furan rings were polymerized with 1,6-hexanediol and 1,4-butanediol, respectively, together with controlled amounts of monofunctional ethyl levulinate to form telechelic ketone-terminated polyesters. Subsequent reactions of these telechelic polyesters with adipic dihydrazide yielded corresponding chain-extended polyesters with increased molecular weights ([η] = 0.29−0.52 dL g<sup>−1</sup>) with acylhydrazone units in the backbone. Thermogravimetric analysis showed a high thermal stability of the polyesters with thermal decomposition only above 275 °C. The polyesters containing the linear hydroquinone units were found to be semicrystalline materials with melting points at 158 and 192 °C, respectively, while those containing the kinked resorcinol units were fully amorphous with glass transition temperatures at 35 and 44 °C, respectively. Initial investigations of the chemical recyclability of the polyesters demonstrated that acylhydrazone units could be selectively cleaved to recover the original telechelic ketone-terminated polyesters, which could again be chain-extended to obtain a recycled polymer with molecular weights and properties very similar to those of the original polymer.<br/>