Polymerization and complexation of methacryloylglycine

Masuda, Seizo; Miyahara, Tomiharu; Minagawa, Keiji; Tanaka, Masami

doi:10.1002/(sici)1099-0518(19990501)37:9<1303::aid-pola10>3.3.co;2-n

Cited by 3 publications

(4 citation statements)

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“…There are two potential explanations for achieving a ligand/metal ratio near 1 as observed in this study. It has been reported that ligand–metal complexes with a net cationic charge can be formed in a 1:1 ratio of COOH:Fe 2+ as illustrated in Figure B. , It is also possible that the steric restriction of the PP substrate and the surrounding carboxylic acids in the PAA grafts inhibit the formation of an octahedral complex structure . Therefore, it is possible to “incompletely” bind iron ions by less than the six total coordination sites.…”

Section: Resultsmentioning

confidence: 93%

“…46,47 It is also possible that the steric restriction of the PP substrate and the surrounding carboxylic acids in the PAA grafts inhibit the formation of an octahedral complex structure. 48 Therefore, it is possible to "incompletely" bind iron ions by less than the six total coordination sites. In this case, while the metal ions retain some activity, it will be inhibited to some extent.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Control of Lipid Oxidation by Nonmigratory Active Packaging Films Prepared by Photoinitiated Graft Polymerization

Tian

Decker

Goddard

2012

J. Agric. Food Chem.

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Transition metal-promoted oxidation impacts the quality, shelf life, and nutrition of many packaged foods. Metalchelating active packaging therefore offers a means to protect foods against oxidation. Herein, we report the development and characterization of nonmigratory metal-chelating active packaging. To prepare the films, carboxylic acids were grafted onto the surfaces of polypropylene films by photoinitiated graft polymerization of acrylic acid. Attenuated total reflectance/Fourier transform infrared spectroscopy, contact angle, scanning electron microscopy, and iron-chelating assay were used to characterize film properties. Graft polymerization yielded a carboxylic acid density of 68.67 ± 9.99 nmol per cm 2 film, with ferrous ironchelating activity of 71.07 ± 12.95 nmol per cm 2 . The functionalized films extended the lag phase of lipid oxidation in a soybean oil-in-water emulsion system from 2 to 9 days. The application of such nonmigratory active packaging films represents a promising approach to reduce additive use while maintaining food quality.

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Section: Resultsmentioning

confidence: 93%

Section: ■ Results and Discussionmentioning

confidence: 99%

Control of Lipid Oxidation by Nonmigratory Active Packaging Films Prepared by Photoinitiated Graft Polymerization

Tian

Decker

Goddard

2012

J. Agric. Food Chem.

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“…Poly(BA- co -SCMHB MA) ([SCMHB MA] = 0−10 mol %) ( II ) was synthesized via free radical copolymerization of I with BA at 3.3 vol % monomer concentration in DMSO in the presence of 0.5 mol % AIBN. DMSO was successfully used as the polymerization solvent in a similar fashion as reported in the earlier literature. − The solution was stirred for 24 h at 60 °C, then precipitated into MeOH, redissolved in CHCl 3 , reprecipitated in MeOH, and dried under vacuum at 60 °C. The SCMHB MA monomer was incorporated in a predictable and quantitative fashion based on 1 H NMR analysis.…”

Section: Methodsmentioning

confidence: 99%

Thermoreversible Poly(alkyl acrylates) Consisting of Self-Complementary Multiple Hydrogen Bonding

2003

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The synthesis and characterization of novel self-complementary multiple hydrogen-bonded (SCMHB) polymers containing pendant 2-ureido-4[1H]-pyrimidone (UPy) units are described. SCMHB pendant polymers, poly(butyl acrylate-co-SCMHB methacrylate), were prepared via free radical copolymerization of butyl acrylate (BA) and a novel SCMHB methacrylate (SCMHB MA) monomer, which was synthesized via a quantitative coupling reaction between 2-isocyanatoethyl methacrylate (ICEMA) and methyl isocytosine (MIS) in DMSO. The glass transition temperatures of poly(BA-co-SCMHB MA) increased in a linear fashion as the SCMHB MA content increased. Thermogravimetric analysis of the copolymers exhibited an onset of weight loss at 217 °C. Solution viscosity analysis indicated that SCMHB pendant polymers strongly aggregated in nonpolar solvents, such as toluene and CHCl3, and dissociated in polar solvents, such as THF. Based on melt rheological characterization, the melt viscosity of soluble SCMHB pendant polymers was an order of magnitude higher than that of PBA due to strong aggregation in the melt state. SCMHB pendant polymers exhibited thermoreversible characteristics, and complete dissociation in the melt state was observed at 80 °C, which was consistent with our earlier studies involving SCMHB-terminated poly(styrene) (PS), poly(isoprene) (PI), and PS-b-PI block copolymers. In addition, SCMHB units completely dissociated at 80 °C in toluene on the basis of 1H NMR measurements. The 90° peel strength values for SCMHB-containing polymers increased as the SCMHB units increased due to the strong interaction of SCMHB units with the glass surface. Thin-layer chromatography indicated that the interaction of SCMHB pendant polymers with silica was more favorable compared to PBA homopolymer.

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“…Even though amide groups formed between cross-linking agents and PAA have oxygen and nitrogen atoms, which could donate a pair of electrons for the formation of a bond with ferrous iron, they may not have been involved in the complexation reaction. The research of Masuda et al 27 indicated that the abilities of polymethacryloylglycine and poly(acrylic acid) to chelate divalent metal ions had no difference, and no additive effect of amide and carboxyl groups was found on the complexation.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Development of an Iron Chelating Polyethylene Film for Active Packaging Applications

Tian

Decker

Goddard

2012

J. Agric. Food Chem.

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Metal-promoted oxidation reactions are a major cause of food quality deterioration. Active packaging offers novel approaches to controlling such oxidation for the purpose of extending shelf life. Herein, we report modification of the surface of polyethylene (PE) films to possess metal chelating activity. Metal chelating carboxylic acids were introduced to the film surface using cross-linking agents [polyethylenimine (PEI) or ethylenediamine (ED)] to increase the number of available carboxylic acids. ATR-FTIR, contact angle, dye assay, and iron chelating assay were used to characterize changes in surface chemistry after each functionalization step. The chelator poly(acrylic acid) (PAA) was attached to the surface at a density of 9.12 ± 0.71 nmol carboxyl groups/cm², and exhibited an iron chelating activity. The results indicate that PAA-modified PE films might have a higher affinity to Fe³⁺ than Fe²⁺ with the optimum binding pH at 5.0. Such inexpensive active packaging materials are promising in food industry for the preservation of liquid and semiliquid food products and have application in heavy metal chelation therapy for biomedical materials as well.

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Polymerization and complexation of methacryloylglycine

Cited by 3 publications

References 0 publications

Control of Lipid Oxidation by Nonmigratory Active Packaging Films Prepared by Photoinitiated Graft Polymerization

Control of Lipid Oxidation by Nonmigratory Active Packaging Films Prepared by Photoinitiated Graft Polymerization

Thermoreversible Poly(alkyl acrylates) Consisting of Self-Complementary Multiple Hydrogen Bonding

Development of an Iron Chelating Polyethylene Film for Active Packaging Applications

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