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This work synthesized a series of symmetrical methylated dialkoxydivanillic acid monomers (Me-RDVAs) with different side-chain lengths (meaning the number of carbons, n, in alkoxy groups, where n = 1, 2, 3 or 4) and methyl (Me), ethyl, propyl or butyl R groups. Homopolyesters were obtained from Me-RDVAs and 1,4-benzenedimethanol, 1,4-cyclohexanedimethanol and 4,4ʹ-biphenyldimethanol, with the aim of producing improved thermal properties. Copolyesters composed of Me-MeDVA together with aliphatic linear diols and cyclic diols were also synthesized. The weight average molecular weights of the resulting polyesters ranged from 1.5 to 11.0 × 104 g/mol and all were thermally stable. Glass transition temperatures varied from 58 to 134 °C. A semi-crystalline polyester with a high melting point of 220 °C was obtained from Me-MeDVA and trans-1,4-cyclohexanedimethanol, and was assessed using polarized optical microscopy and one-dimensional wide-angle X-ray diffraction. Self-standing films of several high molecular weight polyesters were prepared and their mechanical properties assessed.
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•A series of symmetrical methylated dialkoxydivanillic acid (DVA) monomers with varied side-chain lengths were synthesized.•Homo- and copolyesters composed of DVA monomers and cyclic diols (and aliphatic diols for copolyesters) were synthesized.•A semi-crystalline DVA polyester with a melting point of 220 °C was first obtained.•Cast or thermopressing films of DVA polyesters were prepared and their mechanical properties assessed.