In this study, azomethine polyphosphonates were synthesized by solution polycondensation of phenylphosphonic dichloride with various azomethine diols such as [4-(4-hydroxy phenyl) iminomethyl] phenol, [(4-(4-hydroxy-3-methoxy phenyl) iminomethyl)] phenol and [4-(4-hydroxy-3-ethoxy phenyl) iminomethyl] phenol using triethylamine catalyst at ambient temperature. The structure of the synthesized polymers was confirmed by Fourier transform infrared and 1H-, 13C- and 31P- nuclear magnetic resonance spectroscopic techniques. Thermal properties of the polymers were studied by thermogravimetric analysis (TGA) and differential scanning calorimetry under nitrogen atmosphere. The TGA data showed that the synthesized polyphosphonates produce high char yield at 600°C due to the presence of phosphorous atom in the polymer chain and hence have good flame-retardant properties. One of the synthesized polyphosphonate was blended with commercial diglycidyl ether of bisphenol-A (DGEBA) resin in various weight percentage and cured with commercial curing agent triethylene tetramine (TETA). The polyphosphonates-blended epoxy thermosets have tensile strength in the range of 5–41 MPa and the percentage of elongation at breaks was 4–18. It was found that the incorporation of polyphosphonates into epoxy thermoset decreased the tensile strength from 41 MPa to 5 MPa, whereas the elongation at break value increased with increase in the weight percentage of polyphosphonate. The influence of polyphosphonates on the flame retardancy of blended thermosets was examined by limiting oxygen index (LOI) and vertical burning (UL-94) tests and found that the polymer samples achieved an increased UL-94 rating and the LOI values were in the range of 24–26. Broido and Horowitz–Metzger methods have been used to study the thermal degradation kinetic parameters.
Poly(ether–ester)s containing azomethine group in the main chain were synthesized by solution polycondensation of 4,4′-bis(3-hydroxypropyloxy)- N-benzylidene aniline with adipoyl and terephthaloyl diacid chlorides. The synthesized poly(ether–ester)s were characterized by Fourier transform infrared and proton, and carbon-13 nuclear magnetic resonance spectroscopic techniques. Thermal properties were studied using thermogravimetric analysis (TGA) and differential scanning calorimetry. Thermal degradation kinetics of poly(ether–ester)s were characterized by TGA at various heating rates (5°C min−1, 10°C min−1, and 20°C min−1). The apparent activation energy for the degradation of both the polymers was determined by three different non-isothermal model-free kinetics methods (Friedmann, Flynn–Wall Ozawa, and Kissinger–Akahira–Sunose). The photoisomerization property was examined with ultraviolet (UV) spectroscopy, and the polymer PEE1 showed a rate of trans to cis isomerization ranging 10–20 s, whereas reverse process took around 100 min in solution. UV studies suggested that this material may be used in the field of rewritable applications.
Various aliphatic and aromatic diacidchlorides were solution polycondensed with azomethine diol, [(4-(4-hydroxy-3-ethoxy phenyl) iminomethyl)] phenol (HEPIMP), in the presence of triethylamine catalyst at room temperature to produce a series of aliphatic and aromatic azomethine polyesters. Fourier Transform IR and NMR spectroscopy techniques were utilised to analyse the diol monomer HEPIMP. UV-Visible spectroscopy was used to investigate their photoisomerization behaviour in solution. The structure and thermal behaviour of prepared aliphatic and aromatic azomethine polyesters were studied. Limiting oxygen index values were calculated from the Van Krevelen equation to investigate the self-extinguishing character of the synthesised azomethine polyesters, and it was noticed that aromatic polyesters have greater Limiting Oxygen Index value than aliphatic polyesters. The pre exponentional factor (A) and activation energy (Ea) were determined using the Arrhenius, Horowitz-Metzger and Broido models for studying decomposition kinetics.
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