ABSTRACT: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,Ndimethylformamide, 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.
Macroporous copolymer beads with various phenolic derivatives introduced via three types of linkages-amide, methylene, and ether-were prepared from chloromethyl styrene/tetra(ethylene glycol) dimethacrylate copolymer beads. The antioxidation activity of these phenolic copolymer beads was investigated by the measurement of the inhibition activity against the hydroperoxidation of 1,4-dioxane. The phenolic copolymer beads with the dihydroxybenzene moiety exhibited the highest antioxidation activity, and the antioxidation activity of methylene-or ether-linked phenolic copolymer beads was higher than that of amide-linked copolymer beads. Thus, the antioxidation activity of the phenolic copolymer beads was affected by not only the kinds of phenolic moieties attached but also the type of linkage group. In addition, the swelling of the copolymer beads in an organic solvent was greatly affected by the linkage type of the phenolic copolymer beads.
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