Biomimetic design of chelating interfaces

Abstract

Siderophores are naturally occurring small molecules with metal binding constants greater than many synthetic chelators. Herein, we report a two‐step process to graft a siderophore‐mimetic metal chelating polymer from a polypropylene (PP) surface. Poly(methyl acrylate) was first grafted from the PP surface by photoinitiated graft polymerization, followed by the conversion into poly(hydroxamic acid) (PHA) to obtain PP‐g‐PHA films. ATR/FTIR, contact angle, SEM, and AFM were performed to characterize surface properties of films. Iron binding kinetics and the influence of pH (3.0–5.0) on the chelating ability of films were determined. PP‐g‐PHA exhibited significant iron chelating activity (∼80 nmol/cm2) with an equilibration time of 24 h. The materials retained 50% chelating ability at pH 3.0 compared with pH 5.0, almost double the retention of previously reported polycarboxylate chelating interfaces. By using siderophore‐mimetic surface chemistry, such effective metal chelating interfaces can extend the applications of metal chelating polymers in environmental remediation, water purification, and active packaging areas. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015, 132, 41231.

Performance of Nonmigratory Iron Chelating Active Packaging Materials in Viscous Model Food Systems

“…Iron chelating active packaging material was synthesized via photoinitiated graft polymerization of methyl acrylate onto polypropylene (PP) and conversion of grafted poly(methyl acrylate) (PMA) to poly(hydroxamic acid) (PHA) using a method previously reported by Tian and others (). A 2‐step grafting process was used to introduce PMA to the surface of PP films.…”

“…Our research group has developed nonmigratory iron chelating active packaging that is synthesized by polymerization of metal chelating ligands from the surface of packaging materials (Tian and others ; Roman and others ; Tian and others ). This active packaging functions by removing iron from a food to inhibit its reactivity.…”

“…Potent iron chelators, such as EDTA, have demonstrated high efficacy in inhibiting metal‐promoted oxidation in food emulsions (Shimoni and others ; Mei and others ; Mei and others ). The most recent generation of nonmigratory iron chelating active packaging is a polypropylene film from which poly(hydroxamic acid) has been grafted (PP ‐g ‐PHA) (Tian and others ). Hydroxamate‐type chelators have high specificity for iron (for example, deferoxamine B binding constant for ferric iron is 30.4) and maintain activity over a wide range of pH values (Farkas and others ).…”

Synthetic Methodologies for Chelating Polymer Ligands: Recent Advances and Future Development

“…Pre‐irradiation, peroxidation and the method of simultaneous irradiation are used to implement the grafting . For example, grafted siderophore‐mimetic CPLs on the surface of PP and poly(ethylene terephthalate) were obtained by a two‐stage method (Scheme ) …”

“…[53] Pre-irradiation, peroxidation and the method of simultaneous irradiation are used to implement the grafting. [54] For example, grafted siderophore-mimetic CPLs on the surface of PP [55] and poly(ethylene terephthalate) were obtained by a twostage method (Scheme 8). [56] IDA-functionalized materials were prepared using photografting PAA onto PP films followed by a second photo-grafting process to graft-polymerize an IDA functionalized vinyl monomer glycidyl methacrylate (GMA-IDA).…”