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Synthesis of Homo-and Copolyesters Using an AB-Type Aromatic Monomer Based on Homovanillic Acid

Nguyen, Tam T; Olsson, Emma; V. Mankar, Smita; Warlin, Niklas; Valsange, Nitin G; Engqvist, Jonas; Rehnberg, Nicola; Jannasch, Patric; Zhang, Baozhong

DOI:

Abstract

There is currently intensive research ongoing with the aim to utilize various lignin-derived molecules to produce aromatic monomers and polymers. In the present work, (HVA), derived from lignin, was used to prepare sustainable polyesters for the first time. An AB-type monomer with an alcohol group and a carboxylate ester group was conveniently synthesized by using and . The monomer was employed in bulk polycondensation to yield the corresponding homopolyester. The polymerization temperature, catalyst, and time were optimized, and it was found that the addition of a small quantity of a dicarboxylate monomer facilitated a stoichiometric balance throughout the homopolycondensation of the AB-type monomer, and thus significantly enhanced the molecular weight of the polyester (Mn = 36 kg mol−1, [η] ∼ 1.1 dL g−1). Copolymerization of the HVA-based monomer with another lignin-based AB monomer, methyl 4-(2-hydroxyethoxy) benzoate, produced a series of copolyesters with high yields and moderate molecular weights (Mn = 9.5−11 kg mol−1, [η] ∼ 0.5 dL g−1). The resulting copolyesters showed a reasonably high thermal stability (Td,5% > 318 °C) and tunable thermal properties, e.g., Tg = 44−72 °C and Tm = 154−200 °C, depending on the monomeric composition. Consequently, the findings of this work demonstrated the great potential of in the development of new biobased aromatic (co)polyesters with modulated crystallinity.

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Homovanillic acid

A215667306-08-195%

Homovanillic acid

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