Synthesis and properties of bio-based polyesters from a 2,4-dihydroxyacetophenone derivative

Abstract

A novel diphenyl monomer, dimethyl 2,2'-(((ethane-1,2-diylbis(oxy))bis(4-acetyl-3,1-phenylene))bis(oxy))diacetate (EDPD), was synthesized from methyl 2-(4-acetyl-3-hydroxyphenoxy)acetate (MAHA), a 2,4-dihydroxyacetophenonederivative, and combined with 1,4-butanediol, 1,6-hexanediol, 1,4-cyclohexanedimethanol or p-phenylenedimethanolto afford a series of biodegradable polyesters via melt polymerization. The polyesters were characterized by Fourier transform infrared and proton nuclear magnetic resonance spectroscopy, gel permeation chromatography, differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). The weight-average molecular weight (M_w) of the polyesters varied from 3.2–4.4 × 10⁴ g/mol, the glass transition temperature (T_g) from 52 to 80 °C, and the 5% decomposition temperature (T_d,5%) was in the 334–362 °C range. All the samples exhibited high yield strength (53–68 MPa) and elongation at break (230–330%) values, comparable with poly(ethylene terephthalate) (PET), owing to their aromatic character. Degradability testing of the polyesters in soil yielded mass losses reaching up to 7% after 32 weeks. In ecotoxicity testing, earthworms had a survival rate of more than 80% after 14 d of incubation, indicating relatively low toxicity. Overall, the good thermal and mechanical properties, biodegradability and low ecotoxicity of the polyesters make them promising materials for packaging applications, in replacement for PET, thereby promoting carbon neutrality and sustainable development.

Graphical Abstract

Keywords:

• 2,4-Dihydroxyacetophenone
• ecotoxicity
• biodegradability
• thermal properties
• tensile properties

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

This research was funded by the High-end Foreign Experts Programme of the Bureau of Foreign Experts Program (BG20210227001) of the State Administration of Foreign Experts Affairs and the Coal Conversion and New Carbon Materials Hubei Key Laboratory at Wuhan University of Science and Technology (WKDM202109).