Abstract

Τhe production of most polymers depends on fossil resources, which are finite raw materials. In a quest towards more sustainable polymers, natural feedstocks have been explored for the production of monomers for the synthesis of bio-based polymers, mainly cellulose, lignin and polysaccharides [1]. After cellulose, lignin is the second most abundant natural polymer and an important source of aromatic monomers and among them vanillin is a versatile building block for polymer synthesis [2]. Vanillic acid or 4-hydroxy-3-methoxybenzoic acid, obtained by vanillin oxidation, is a potentially bio-based building block, which has recently regained attention. Poly(ethylene vanillate) was thus synthesized and studied, exhibiting promising characteristics [3]. Poly(ethylene furanoate) (PEF) is the most prominent member of the family of furandicarboxylate-based polyesters and is considered as a potential substitute of poly(ethylene terephthalate) (PET). In the present work, the preparation of poly(ethylene furanoate-co-ethylene vanillate) copolymers (PEFV) will be presented. PEFV copolymers were obtained by the traditional two-step melt polycondensation method. PEFV copolymers were structurally characterized by nuclear magnetic resonance spectroscopy (NMR), while their thermal behavior and thermal stability was studied by differential scanning calorimetry and thermogravimetric analysis. [1] Hillmyer, M.A. The promise of plastics from plants. Science 2017, 358, 868 [2] Fache, M.; Darroman, E.; Besse, V.; Auvergne, R.; Caillol, S.; Boutevin, B. Vanillin, a promising biobased building-block for monomer synthesis. Green Chem. 2014, 16, 1987 [3] Zamboulis, A.; Papadopoulos, L.; Terzopoulou, Z.; Bikiaris, D.N.; Patsiaoura, D.; Chrissafis, K.; Gazzano, M.; Lotti, N.; Papageorgiou, G.Z. Synthesis, Thermal Properties and Decomposition Mechanism of Poly(Ethylene Vanillate) Polyester, Polymers 2019, 11, 1672

Highlights

  • Sustainable polymers & Lignin Monomers based on renewable sources afford green polymers Lignin is the second most abundant natural polymer Source of aromatic monomersVanillic acid Produced by vanillin oxidation Biobased aromatic building block Poly(ethylene vanillate) has comparable thermal properties to PETPoly(ethylene furanoate) (PEF) One of the most important biobased polymers Exceptional barrier properties (O2 and CO2) Superior thermal stability and lower melting temperature than PETOur goals Prepare poly(ethylene furanoate)/poly(ethylene copolymers (PEFV) Study the thermal behavior and stability vanillate) SynthesisSynthesis of 2-hydroxyethyl vanillic acidSynthesis of copolymers by two-step melt polycondensation: i. transesterification ii. polycondensation.Synthesis of poly(ethylene 2,5-furandicarboxylate) oligomersMolar ratio F/V units: 95:05, 90:10, 80:20

  • Thermal stability decreases with increasing vanillic content

  • ✓ PEFV block copolymers were successfully synthesized. ✓ Composition is consistent with the feed ratio. ✓ As received samples were completely amorphous. ✓ Tg temperatures range around 80 °C

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Summary

Introduction

Synthesis of 2-hydroxyethyl vanillic acidSynthesis of copolymers by two-step melt polycondensation: i. transesterification ii. polycondensation.Synthesis of poly(ethylene 2,5-furandicarboxylate) oligomersMolar ratio F/V units: 95:05, 90:10, 80:20. [1] Department of Chemistry, Aristotle University of Thessaloniki, GR-541 24, Thessaloniki, Greece [2] Chemistry Department, University of Ioannina, P.O. Box 1186, GR-45110, Ioannina, Greece Monomers based on renewable sources afford green polymers

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