Retention behavior of hydroxybenzene derivatives on polymer resin immobilized with macrocyclic polyamines

Four kinds of macrocyclic polyamine (MCPA)-immobilized polymer resins were prepared by reacting macroreticular-type chloromethylated polystyrene (CPS) with [9]aneN3, [14]aneN4, [15]aneN5 and [18]aneN6. The retention times of the solutes (dihydroxybenzene, hydroxybenzoic acid and dihydroxybenzoic acid isomers) were measured for a column packed with the MCPA-immobilized polymer resin by using a liquid-chromatographic method. Phosphate buffer solutions of pH 1.8, 4.5 and 6.8 were used as eluents. The distribution coefficients of the solutes on the MCPA-immobilized polymer resin were calculated from the capacity factors obtained by the retention time and volume of the resin and liquid phases in the column. Linear polyamines, such as diethylenetriamine and triethylenetetramine, were immobilized on the polymer resin, and the distribution coefficients of the solutes on these resins were measured as well as the unmodified resin for a comparison with the MCPA-immobilized polymer resin. The MCPA-immobilized polymer resins showed higher adsorptivity for the solutes than did the linear polyamine-immobilized polymer resin. Especially, the [15] aneN5-immobilized polymer resin showed selective adsorptivity for the isomers of dihydroxybenzene among the MCPA-immobilized polymer resin. The distribution coefficients of the MCPA-immobilized polymer resin for hydroxybenzene isomers increased in the order para