Naturally occurring nipagin and eugenol were used as the collaborative starting materials for poly(ether ester) polymers. In this study, two series of nipagin and eugenol-derived copoly(ether ester)s, PHN1 1−x E1 x and PHN1 1−x E2 x (x = 0%, 5%, 10%, 15%, 20%), were prepared with renewable 1,6-hexanediol as a comonomer. The nipagin-derived component acts as the renewable surrogate of petroleum-based dimethyl terephthalate (DMT), while the eugenol-derived component acts as the cooperative property modifier of parent homopoly(ether ester) PHN1. 1,6-Hexanediol was chosen as the spacer because of its renewability, high boiling point, and short chain to enhance the glass transition temperatures ( T g s) of materials. The molecular weights and chemical structures were confirmed by gel permeation chromatograph (GPC), NMR and FTIR spectroscopies. Thermal and crystalline properties were studied by thermal gravimetric analysis (TGA), differential scanning calorimetric (DSC) and wide-angle X-ray diffraction (WXRD). The tensile assays were conducted to evaluate the mechanical properties. The results suggested that properties of this kind of poly(ether ester)s could be finely tuned by the relative content of two components for the desired applications (elastomer, rubbery) suitable for different scenarios from polyethylene glycol terephthalate (PET) and polybutylene terephthalate (PBT).
To improve the crystalline and mechanical properties of bio-based polyester materials, highly symmetrical nipagin-derived dimethyl ester is used for the synthesis of polyesters. Aromatic copolyesters, PDN21−xE1x and PDN21−xE2x (x = 0%, 10%, 20%, 30%, 40%, and 50%), with high crystallinity are synthesized from bio-based 1,10-decanediol, nipagin and eugenol-derived dimethyl esters via a random copolymerization method. The crystallizability of the copolyesters is emphatically investigated by the content of the two asymmetrical eugenol-derived compositions (i.e. E1 and E2). Not only the appearance of the copolyesters, which present a white powder consistently, but also differential scanning calorimetry (DSC), wide-angle X-ray diffraction (WXRD) and isothermal crystallization analyses verify the strong crystallizability of the copolyesters despite the fact that the crystallinity (Xc), melting point (Tm) and corresponding enthalpy (ΔHm) are found to gradually decrease with the increase in the eugenol-based composition. Furthermore, the tensile assays demonstrate brittle characteristics of the copolyesters and further confirm the strong crystallizability of the nipagin-based PDN2, a potential candidate for replacement of the petroleum-based polyethylene (butylene) terephthalate (PET, PBT).
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