Cyclic dithia/diaza with dual Schiff base linkage functionalized polymers for heavy metal adsorption

Three new types of functionalized polystyrene-divinylbenzene resins containing two sulfur and two nitrogen atoms and four nitrogen atoms in cyclic form were prepared by using two lab-synthesized ligands; 2-[3-(2-amino ethylsulfanyl)-propylsulfanyl]-ethylamine (AEPE) and 2-[2-(2-amino-ethylsulfanyl)-ethylsulfanyl]-ethylamine (AEEE), and a commercial one; triethylenetetramine (TETA). Chloromethylated polystyrene-divinylbenzene copolymer (Cl-PS-DVB) was initially oxidized to aldehydic polystyrene-divinylbenzene (CHO-PS-DVB) with approximately 57% yield. CHO-PS-DVB was subsequently reacted with the ligands through dual Schiff base linkage. The products were named AEPE-PS-DVB, AEEE-PS-DVB and TETA-PS-DVB, respectively. The optimum coupling reaction times and temperatures were 6 h at 50°C for AEPE-PS-DVB, AEEE-PS-DVB and 6 h at room temperature for TETA-PS-DVB. The appropriate amount of the three ligands was 2.65 mmol/g CHO-PS-DVB corresponding to the mole ratio between the chelating ligand and aldehyde group of 1 : 2. All derivative resins were characterized by elemental analysis, thermogravimetry, FT-IR and FT-Raman spectroscopy and Ninhydrin test. The adsorption properties of the synthesized resins towards Pb(II), Cu(II), Cd(II), Zn(II), Ni(II), Co(II) and Cr(III) ions in aqueous solution were preliminarily investigated by batch method. AEPE-PS-DVB and AEEE-PS-DVB showed the same sorption behavior. Their selectivity order was Pb(II) > Zn(II) > Cu(II) > Cd(II) and no significant adsorption for Co(II), Ni(II), Cr(III) was observed. In addition, TETA-PS-DVB showed a selectivity toward only Pb(II). © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2010

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