Wholly aromatic poly(azomethine)s with 1,5‐ or 2,6‐substituted naphthalene moiety in the main chains were prepared in aprotic polar solvents or m‐cresol under various reaction conditions. In the polymerization of 1,5‐diaminonaphthalene with terephthalaldehyde, the polymer that synthesized in (HMPA/DMSO) at room temperature for 24 h by adding 5 wt % of calcium chloride and a very small amount of p‐toluenesulfonic acid showed the highest reduced viscosity in all of the polymers from 1,5‐diaminonaphthalene. The reduced viscosity of poly(azomethine)s synthesized from 2,6‐diaminonaphthalene with 2,6‐diformylnaphthalene in m‐cresol and with terephthalaldehyde in HMPA/DMSO were ηred = 0.35 and 0.36, respectively. The thermal analysis showed the poly(azomethine)s had high thermal stability and the glass‐transition temperatures of these polymers are about 250 °C. The X‐ray diffraction showed that they are partially crystalline. They could be polymerized again by second stage polycondensation in polyphosphoric acid. The reduced viscosities of the obtained polymers were about 2–5 times as high as that of the pristine polymers. © 2000 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 38: 1064–1072, 2000
Model reaction of bis(4‐nitrophenyl) β‐truxinate (BNPT) with aliphatic amines proceeded quantitatively at room temperature. Accordingly, polycondensation of BNPT with various diamines was carried out at room temperature or 80°C. During the polycondensation of BNPT with diamines, the precipitation of polymer or the observed gelation of polymerization solution occurred, which may limit the molecular weight of the polymer. On the other hand, the reaction of BNPT with 1,3‐(4‐piperidyl)propane (DPP) proceeded homogeneously to give the polymer with relatively high molecular weight, and the obtained polyamide (P‐1e) showed excellent solubility in many solvents. The study of TG and DTA indicated that the obtained polymers were stable at lower temperature than around 270°C. The polymer prepared from the polycondensation of BNPT with hexamethylenediamine showed melting point and decomposition due to the imidation at 282°C. The photochemical reaction of these polymers was carried out in the film state. The irradiation of 254 nm light caused an absorption at 272 nm to appear and the molecular weight to decrease. This meant that the scission of cyclobutane ring in the main chain occurred to give cinnamamide structures. Also, the absorption at 272 nm decreased by the irradiation of 302.5 nm light. However, the UV spectrum of irradiated polymer did not agree with that of the original polymer. These results suggested that the dimerization of the resulting cinnamamide moieties occurred in the competition of their trans–cis‐isomerization. On the other hand, the rate of scission of cyclobutane ring of P‐1e was faster than that of the corresponding polyamide containing α‐truxillamide structure.
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