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Synthesis of macroporous polymers with radical scavenging properties by immobilization of polyphenolic compounds

journal contribution
posted on 2023-05-17, 14:24 authored by Arrua, RD, Basbus, JF, Strumia, MC, Alvarez Igarzabal, CI, Nazareno, MA
Solid phase radical scavengers have been prepared by the immobilization of antioxidant (AOX) compounds on macroporous polymers. Poly(glycidylmethacrylate-co-trimethylolpropane trimethacrylate)[poly(GMA-TRIM)] and poly(N-acryloyl-tris(hydroxymethyl)aminomethane-co-glycidylmethacrylateco-N,N0-methylenebisacrylamide) [poly(NAT-GMA-BIS)] were prepared by free radical polymerization using a mixture of dimethylsulfoxide (DMSO)-poly(ethyleneglycol) 6000 (PEG 6000) as a porogenic solvent. The polymers were aminated with ethylenediamine (EDA) and the linkage of the polyphenolic compounds (gallic and caffeic acids) was carried out by two different approaches: through N,N0-dicyclohexylcarbodiimide/4-dimethylaminepyridine (DCC/DMAP) system (one-step method) or through the previous formation of the acyl chloride of the polyphenolic compounds and subsequent amidation reaction (two-step method). The available phenolic groups on the macroporous polymers were determined using the Folin-Ciocalteu method; the radical scavenging properties of the materials prepared were evaluated using the radical species 1,1-diphenyl-2-picrylhydrazyl radical (DPPH.) and 2,20-azinobis-[3-ethylbenzothiazoline-6-sulfonic acid] radical cation (ABTS+). From the results, higher antiradical capacities were obtained with the polymers in which the immobilization of the antioxidant molecules was performed through the two-step method. The polymeric networks prepared in this work yielded up to 13.2 umol AOX/g of dry polymer, which allowed a quantitative removal of the radicals tested in less than 30 min.

History

Publication title

Reactive and Functional Polymers

Volume

72

Issue

11

Pagination

807-813

ISSN

1381-5148

Department/School

School of Natural Sciences

Publisher

Elsevier Science Bv

Place of publication

Po Box 211, Amsterdam, Netherlands, 1000 Ae

Rights statement

Copyright 2012 Elsevier.

Repository Status

  • Restricted

Socio-economic Objectives

Expanding knowledge in the chemical sciences

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