Synthesis of chloromethylstyrene-tetraethyleneglycol dimethacrylate copolymer beads having various phenolic derivatives immobilized via amide bond and their antioxidation activity

Resins having phenolic derivatives were prepared by treating a resin (RAS-4G), having benzylamino groups, with benzoic acids containing phenolic hydroxyl groups. The RAS-4G was prepared by treating macroreticular chloromethylstyrene-tetraethyleneglycol dimethacrylate (4G) copolymer beads with potassium phthalimide in N,N-dimethylformamide, followed by reflux in an ethanol/hydrazine monohydrate mixture. 4-Hydroxy benzoic acid, (2,4-, 3,4-, and 3,5-)dihydroxy benzoic acids, 3,4,5-trihydroxy benzoic acid, etc., were used as benzoic acids with phenolic hydroxyl groups. The antioxidation ability of the resins having phenolic derivatives was investigated against the generation of 1,4-dioxane hydroperoxide. The resins showed high inhibition ability against the generation of hydroperoxide. In particular, the resin (RAS-4G-3,4-DHBA) having two phenolic hydroxyl groups had the highest inhibition ability. The resins were found to act as radical scavengers during the generation of 1,4-dioxane hydroperoxide by UV irradiation in the presence of oxygen.