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

Abstract

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.

Synthesis of macroreticular copolymer beads having various phenolic derivatives immobilized via different bond and their radical scavenging activity

“… via amide bond : Macroreticular copolymer beads (RCS‐4G) (CMS:4G = 90:10 molar ratio) were prepared by suspension copolymerization of CMS and 4G using AIBN as an initiator as described already 9. The RCS‐4G had 1.1 cm 3 /g of pore volume, 500 Å of average pore radius, and 30 m 2 /g of specific surface area.…”

“…And we have previously reported that the macroreticular copolymer beads having phenolic derivatives immobilized via amide bond exhibited an antibacterial activity against bacteria such as E. coli or S. aureus. 8 Recently we found that the copolymer beads had also an inhibition activity against the generation of 1,4‐dioxane hydroperoxide in the presence of oxygen by UV irradiation and the copolymer beads could be easily reused without a decrease of the inhibition activity 9. And the relationship between the antibacterial activity or the inhibition activity and the structure of phenolic derivatives immobilized has also been discussed 8, 9.…”

“…8 Recently we found that the copolymer beads had also an inhibition activity against the generation of 1,4‐dioxane hydroperoxide in the presence of oxygen by UV irradiation and the copolymer beads could be easily reused without a decrease of the inhibition activity 9. And the relationship between the antibacterial activity or the inhibition activity and the structure of phenolic derivatives immobilized has also been discussed 8, 9. So far many researchers have studied the antioxidation mechanism by phenolic compounds from the theoretical or experimental point of view 10–13.…”

Synthesis of copolymer beads with various phenolic derivatives attached via different linkages and their antioxidation activity

“…[21][22][23][24][25][26] In our previous studies, 27,28 copolymer beads containing various phenolic derivatives were synthesized, and the radical quenching abilities were evaluated. In the results, the radical quenching abilities were much affected by the position of the hydroxy group and the type of linkage between the phenolic moiety and polymer matrices.…”

Synthesis, Characterization and Radical Scavenging Ability of 3,5-di-tert-Butyl-4-hydroxyphenoxy-Functionalized Polynorbornenes Synthesized Using Ring-Opening Metathesis Polymerization

“…Among these, radical scavenging functional polymers have emerged as powerful tools that are suitable for polymeric stabilizers, self-stabilized materials, biomedical materials and packing materials [2][3][4][5][6]. Our interest in the development of radical scavenging polymer based on sterically hindered phenol (SHP) function-alized norbornene derivatives and ring-opening metathesis polymerization (ROMP) strategies had led us to recently communicate a series of polymers bearing SHP group in the side-chain and their performance in the scavenging of radicals.…”