Synthesis and Characterization of Poly(amide-ester)s Containing Naphthalene Pendent Groups and Urazole Rings

4-(3-Hydroxy-naphthalene)-1,2,4-triazolidine-3,5-dione (3HNTD) was synthesized in six steps starting from 3-hydroxy-2-naphthalene carboxylic acid. The reaction of monomer 3HNTD with acetyl chloride was performed in N,N-dimethylacetamide (DMAc) solution at different molar ratios, and the resulting mono-, di- and trisubstituted derivatives were obtained in high yields and were finally used as models for polymerization reactions. A series of novel aliphatic–aromatic poly(amide-ester)s (PAE)s containing a naphthalene pendent moiety were prepared from 3HNTD and various diacid chlorides (including succinyl chloride, adipoyl chloride and sebacoyl chloride) by polycondensation reactions with three methods: low-temperature solution polycondensation, solution polymerization under gradual heating and reflux conditions in the presence of pyridine and triethylamine as a proton scavenger and without a proton scavenger, respectively. PAEs from aliphatic diacid chlorides and 3HNTD have been studied in great detail via th...