The oxidative polycondensation of benzylidene-4 '-hydroxyanilene using air O-2, NaOCl and H2O2: Synthesis and characterization

Kaya I., Culhaoglu S.

JOURNAL OF POLYMER RESEARCH, vol.12, no.2, pp.113-119, 2005 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 12 Issue: 2
  • Publication Date: 2005
  • Doi Number: 10.1007/s10965-004-2502-6
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.113-119
  • Keywords: air O-2, H2O2, NaOCl, oligo-benzylidene-4 '-hydroxyanilene, oxidative polycondensation, thermal analysis, SCHIFF-BASE OLIGOMERS
  • Çanakkale Onsekiz Mart University Affiliated: Yes


In this work, the oxidative polycondensation reaction conditions of benzylidene-4'-hydroxyanilene (B-4'-HA) were studied using oxidants such as air O-2, H2O2 and NaOCl in an aqueous alkaline medium between 40 and 95 degrees C. Oligo-benzyfidene4'-hydroxyanilene was characterized by H-1-NMR, FT-IR, UV-Vis, size exclusion chromatography (SEC) and elemental analysis techniques. The solubility of oligomer using organic solvents such as DMF, THF, DMSO, methanol, ethanol, CHCl3, CCl4, toluene, acetonitrile, ethyl acetate was investigated. According to air O-2 oxidant (flow rate 8.5 L/h), the conversion of B-4'-HA was 82.0% in optimum conditions such as [B-4'-HA](0) = [KOH](0) = 0.1015 mol/L at 50 degrees C for 25 h. According to the SEC analysis, the number-average molecular weight (M-n), weight-average molecular weight (M-w) and polydispersity index (PDI) values of O-B-4'-HA were found to be 1852 gmol(-1), 3101 gmol(-1) and 1.675; 2123 gmol(-1), 4073 g mol(-1) and 1.919; 2155 gmol(-1), 4164 gmol(-1) and 1.932, using air oxygen, NaOCl and H2O2 oxidants, respectively. Also, Thermo gravimetric analysis (TGA) showed oligo-benzylidene-4'-hydroxyanilene to be unstable against thermo-oxidative decomposition. The weight loss of O-B-4'-HA was found to be 95.87% at 1000 degrees C.