Synthesis of polyesters mimicking polyethylene terephthalate and their thermal and mechanical properties
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ORIGINAL PAPER
Synthesis of polyesters mimicking polyethylene terephthalate and their thermal and mechanical properties Gulsah Kurt1 · Ersen Gokturk2 Received: 17 June 2020 / Accepted: 10 September 2020 © The Polymer Society, Taipei 2020
Abstract Poly (dihydroferulic acid) (PHFA) from biorenewable vanillin was reported before as an alternative replacement of polyethylene terephthalate (PET). Thermal properties of PHFA were found to be very close to those of commercial polyethylene terephthalate (PET). However, PHFA was insoluble in common organic solvents, and it was difficult to measure molecular weight of the obtained polymer due to difficulty of performing gel permeation chromatography (GPC) analysis. In order to modulate the physical properties of PHFA, here we report a new kind of polyester synthesized from ethyl vanillin instead of vanillin as a starting material. Ethyl group on the monomer was found to disrupt the crystallinity, improve the thermal properties and increase the solubility of the obtained polymer. 3-(4-acetoxy)-3-ethoxyphenyl) propanoic acid (AEPPA) was obtained from the reaction between ethyl vanillin and acetic anhydride through Perkin reaction and subsequent hydrogenation. Polycondensation of AEPPA was achieved using zinc acetate catalyst and resulted in poly (3-(4-acetoxy)-3-ethoxyphenyl) propanoic acid) with 75% yield and high solubility in common organic solvents. Thermal transition temperatures of the obtained polymer are very close to those of commercial PET. Polycondensation was further extended to copolymerization of AEPPA and monomers derived from vanillin and syringaldehyde. Synthesized copolymers also showed higher solubility and tunable thermal properties compared to the PHFA from vanillin. Keywords Biorenewable · Polyester · Ethyl vanillin · Zinc acetate · Polyethylene terephthalate
Introduction Thermoplastics enter into our daily life as a variety of products including bottles, packaging materials, consumer products, etc. [1]. The dominated commercial polymers used in the plastic market mainly consist of polyethylene (PE), polystyrene (PS), polyvinylchloride (PVC), polypropylene (PP), polycarbonate (PC), and PET [2, 3]. These thermoplastics have some good properties; such as, low cost, resistance to chemical materials, unique thermal and mechanical Electronic supplementary material The online version of this article (https://doi.org/10.1007/s10965-020-02285-0) contains supplementary material, which is available to authorized users. * Gulsah Kurt [email protected] 1
Department of Chemistry, Faculty of Arts and Sciences, Aksaray University, 68100 Aksaray, Turkey
Department of Chemistry, Hatay Mustafa Kemal University, 31001 Hatay, Turkey
2
properties. However, these polymers are mostly produced from finite fossil fuel resources [2, 3]. Despite being the most valuable products in the plastic industry, thermoplastics have some major problems due to the limited supplies of petroleum based materials, difficulties in recycling and environmental pollution since their
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