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

Abstract

AbstractResins 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. © 2005 Wiley Periodicals, Inc. J Appl Polym Sci 97: 2097–2104, 2005