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Novel heat-resistant and soluble poly(amide–ether)/zinc oxide nanocomposites: synthesis, characterization and computational study

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Abstract

Novel heat-resistant poly(amide–ether)/zinc oxide nanocomposites containing two different types of ZnO nanoparticles were successfully prepared by a solution intercalation technique. A new poly(amide–ether) (PAE) as a source of polymeric matrix was synthesized by direct polycondensation reaction of new diamine containing 1,3,4-oxadiazole and biphenyl groups with 4,4′-(butane-1,4-diylbis(oxy))dibenzoic acid in a medium consisting of N-methyl-2-pyrrolidone,triphenyl phosphite, calcium chloride, and pyridine. Fourier-transform infrared (FTIR), nuclear magnetic resonance (1H NMR), and UV–Vis technique were used for characterization of as-synthesized PAE. The synthesized PAE revealed good solubility in dipolar aprotic solvents at room temperature and the inherent viscosity of the PAE in DMF at a concentration of 0.01 g dL−1 at 25 °C was 0.34 dL/g. Improved solubility was attributed to the presence of flexible ether linkage in the polyamide backbones that reduce the chain–chain interaction and enhance solubility by penetrating solvent molecules into the polyamide chains. The structural and electronic properties of PAE units were studied by ab initio density functional theory method using the B3LYP/6-31G (d) level of theory. Due to incorporation of biphenyl group as an electron donor on the 1,3,4-oxadiazole ring in the structure of PAE, the highest occupied molecular orbitals (HOMO) are localized mainly on biphenyl group. The calculated absorption spectrum of the studied PAE exhibited the maximum absorption wavelength which corresponds to the electronic transition from the HOMO-1 to LUMO with 92% contribution. Zinc oxide nanoparticles were synthesized by a direct precipitation method from zinc nitrate solution and were modified with 1-methyl-3-(trimethoxysilylpropyl) imidazolium chloride. The PAE/ZnO nanocomposite films were prepared by simple dissolution technique using 3 wt% of ZnO nanoparticles and modified ZnO nanoparticles. The morphology, crystalline phase, and thermal stability of the resultant materials were characterized by field emission scanning electron microscopy (FE-SEM), X-ray diffraction (XRD), energy-dispersive X-ray (EDX), thermal gravimetric analysis (TGA), and FTIR techniques. The FE-SEM analysis showed better dispersion of ZnO@ImCl nanoparticles within the poly(amide–ether) matrix in comparison with ZnO nanoparticles, which arises from high interactions between ZnO@ImCl and the PAE chains. Thermogravimetric analysis results indicated improving on thermal properties of the poly(amide–ether) nanocomposites as compared with the neat poly(amide–ether). The incorporation of functional ZnO@ImCl nanoparticles could further improve the thermal properties of poly(amide–ether). The high interaction between poly(amide–ether) and ZnO@ImCl nanoparticles, the presence of oxadiazole, ether, amide and imidazole content of the ZnO@ImCl nanoparticles seem to be responsible for the improvement of the thermal properties. Furthermore, the presence of oxadiazole, ether, amide and bulky biphenyl groups in the poly(amide–ether) backbone increased the solubility in organic solvents.

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Authors and Affiliations

  1. Department of Chemistry, Dezful Branch, Islamic Azad University, Dezful, Iran

    Shirin Faridi & Hassan Moghanian

  2. Faculty of Chemistry and Petrochemical Engineering, Standard Research Institute (SRI), P.O. Box 31745-139, Karaj, Iran

    Meisam Shabanian

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  1. Shirin Faridi
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  2. Hassan Moghanian
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Correspondence to Hassan Moghanian.

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Faridi, S., Moghanian, H. & Shabanian, M. Novel heat-resistant and soluble poly(amide–ether)/zinc oxide nanocomposites: synthesis, characterization and computational study. Polym. Bull. 75, 4445–4468 (2018). https://doi.org/10.1007/s00289-018-2280-7

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