Synthesis,characterization, and thermal degradation of oligo‐2‐(morpholinoiminomethyl)phenol and its Pb(II) complex compound

The oxidative polycondensation reaction conditions of 2‐(morpholinoiminomethyl)phenol were studied with H₂O₂, air O₂, and sodium hypochloride (NaOCl) oxidants in an aqueous alkaline medium between 40 and 90°C. The structure of oligo‐2‐(morpholinoiminomethyl)phenol was characterized with ¹H‐ and ¹³C‐NMR, Fourier transform infrared, ultraviolet–visible, size exclusion chromatography, and elemental analysis techniques. Under the optimum reaction conditions, the yield of oligo‐2‐(morpholinoiminomethyl)phenol was 28% for the H₂O₂ oxidant, 12% for the air O₂ oxidant, and 58% for the NaOCl oxidant. According to the size exclusion chromatography analysis, the number‐average molecular weight, weight‐average molecular weight, and polydispersity index of oligo‐2‐(morpholinoiminomethyl)phenol were 2420 g/mol, 2740 g/mol, and 1.187 with H₂O₂, 1425 g/mol, 2060 g/mol, and 1.446 with air O₂, and 1309 g/mol, 1401 g/mol, and 1.070 with NaOCl, respectively. Thermogravimetry/dynamic thermal analysis showed that the oligo‐2‐(morpholinoiminomethyl)phenol–lead complex compound was more stable than 2‐(morpholinoiminomethyl)phenol and oligo‐2‐(morpholinoiminomethyl)phenol against thermal degradation. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 102:3795–3804, 2006