Removal of allergens from natural oils by selective binding to polymer supports. II. Application of aminated resins to isoalantolactone and costus oil

A number of crosslinked polymers containing primary or secondary amine functional groups were prepared by chemical modification of styrene–divinylbenzene or styrene–acrylonitrile–divinylbenzene resins. The polymers were tested in the binding of α-methylene-γ-butyrolactone allergens via Michael addition of their nucleophilic ends with the conjugated system of the lactones. Best results were obtained using 1% crosslinked poly(aminoethylstyrene) in ethanol; polymers with higher crosslinking or other functional groups were somewhat less reactive. This technique for the removal of α,β-unsaturated lactones from solution was applied successfully to the selective removal of the allergenic components of costus oil, a natural oil of plant origin used in the cosmetics industry. After purification of the costus extracts, the allergens which were retained by the polymer could be cleaved by permethylation followed by base treatment, and characterized. The polymer-treated natural oil had lost its allergenic properties while the polymer-retained materials were found to be powerful allergens.