Photo‐Curable Metal‐Chelating Coatings Offer a Scalable Approach to Production of Antioxidant Active Packaging

Lin, Zhuangsheng; Goddard, Julie M.

doi:10.1111/1750-3841.14051

Cited by 30 publications

(26 citation statements)

References 52 publications

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“…The ability of granulated PLA, cross-linked PLA, and antioxidant functionalized PLA films to prevent oxidative degradation of ascorbic acid was measured as performed in Herskovitz & Goddard, 2020 39 and others. 36,62 Briefly, 1 x 1 cm 2 film samples were incubated with 1 ml of 20 mM ascorbic acid solution in 10 mM sodium acetateimidazole buffer, pH 4 within 10 ml glass GC vials and aluminum septum caps at 37 C for 9 days. Samples were assessed for ascorbic acid concentration at specified timepoints (day 0, day 1, day 3, day 5, and day 9) using a modified version of the Association of Official Analytical Chemists method 967.21.38.…”

Section: Accelerated Ascorbic Acid Degradation Studymentioning

confidence: 99%

Antioxidant functionalization of biomaterials via reactive extrusion

Herskovitz

Goddard

2021

J of Applied Polymer Sci

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Concern over environmental contamination and the need for industrially produced functional biopolymers motivates the utilization of reactive extrusion for functional grafting. Antioxidant nonmigratory active materials were synthesized through 1,3-bis(4,5-dihydro-2-oxazolyl)benzene ring opening polymerization with bio-based poly(lactic acid) (PLA) and antioxidant nitrilotriacetic acid (NTA). Grafting was confirmed through the introduction of new alkyl stretching, disappearance of the characteristic 1,3-bis(4,5-dihydro-2-oxazolyl)benzene band, and emergence of new amide band on attenuated total reflectance Fourier transform infrared spectroscopy. X-ray photoelectron spectroscopy (XPS) showed stepwise increases in atomic nitrogen percentage and shifts in proportion of CC:CO bonding, confirming grafting and surface orientation. Antioxidant samples exhibited significant increases in carboxylate density, ranging from 0.75 ± 0.04 to 3.11 ± 0.04 nmol/cm 2. Functionalized films demonstrated significant antioxidant properties with Trolox (eq) ranging from 0.36 ± 0.02 to 0.89 ± 0.07 nmol/cm 2 according to radical scavenging studies and delayed greater than 52% of ascorbic acid degradation. This work develops a rapid functionalization method for biopolymers and displays efficacy in producing sustainable nonmigratory active materials.

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Section: Accelerated Ascorbic Acid Degradation Studymentioning

confidence: 99%

Antioxidant functionalization of biomaterials via reactive extrusion

Herskovitz

Goddard

2021

J of Applied Polymer Sci

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“…Moreover, the aqueous composition (for example, metal ions and oxygen) can be controlled to inhibit lipid oxidation. Metal chelators such as EDTA have been widely used to inhibit lipid oxidation (Alamed, Mcclements, & Decker, 2006;Lee & Decker, 2011;Nielsen, Petersen, Meyer, Timm-Heinrich, & Jacobsen, 2004), but an increasing demand for clean-label products has advanced recent researches on natural metal chelators (Todokoro, Fukuda, Matsumura, Irie, & Hata, 2016) and active packaging with metal-chelating properties (Lin & Goddard, 2018;Tian, Decker, Mcclements, & Goddard, 2014). Unabsorbed emulsifiers available in the aqueous phase are also believed to be able to inhibit oxidation (Berton-Carabin et al, 2014).…”

Section: Physical Statementioning

confidence: 99%

Synthesis, physicochemical properties, and health aspects of structured lipids: A review

Guo

Cai

Xie

et al. 2020

Comp Rev Food Sci Food Safe

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Structured lipids (SLs) refer to a new type of functional lipids obtained by chemically, enzymatically, or genetically modifying the composition and/or distribution of fatty acids in the glycerol backbone. Due to the unique physicochemical characteristics and health benefits of SLs (for example, calorie reduction, immune function improvement, and reduction in serum triacylglycerols), there is increasing interest in the research and application of novel SLs in the food industry. The chemical structures and molecular architectures of SLs define mainly their physicochemical properties and nutritional values, which are also affected by the processing conditions. In this regard, this holistic review provides coverage of the latest developments and applications of SLs in terms of synthesis strategies, physicochemical properties, health aspects, and potential food applications. Enzymatic synthesis of SLs particularly with immobilized lipases is presented with a short introduction to the genetic engineering approach. Some physical features such as solid fat content, crystallization and melting behavior, rheology and interfacial properties, as well as oxidative stability are discussed as influenced by chemical structures and processing conditions. Health‐related considerations of SLs including their metabolic characteristics, biopolymer‐based lipid digestion modulation, and oleogelation of liquid oils are also explored. Finally, potential food applications of SLs are shortly introduced. Major challenges and future trends in the industrial production of SLs, physicochemical properties, and digestion behavior of SLs in complex food systems, as well as further exploration of SL‐based oleogels and their food application are also discussed.

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“…Copolymers enable combining the functional or mechanical properties of more than one homopolymer in a single material [4] making them useful in a wide array of applications that require multiple polymer characteristics such as clothing, rubbers, latex paints, materials for automobiles, electronics, furniture, construction materials, packaging, adhesives and biomedical applications [5] . For example, some polymer functionalities useful for applications in active packaging could include a metal chelating ligand that improves the food's shelf-stability and a UV-curable moiety that promotes its application in high-throughput industrial processes because they do not require solvents nor high energy inputs to cure [6] , [7] , [8] .…”

Section: Additional Informationmentioning

confidence: 99%

General method for emulsion polymerization to yield functional terpolymers

2020

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Copolymerization methods are used to impart specific, desired functional properties (e.g. mechanical or bioactive) to a material for targeted applications in biomedicine, food and agriculture, consumer products, advanced manufacturing, and more. Many polymerization methods exist to achieve tailored copolymer architectures. Of them, emulsion polymerization offers unique and industrially convenient features that make for easily scalable processes because the synthesis occurs in water and the latexes usually do not need further purification. Because of the breadth of copolymer architectures and thus wide range of potential applications for latexes produced by emulsion polymerization, there is great value in defining general methods for emulsion polymerizations to yield copolymers, including routes for synthesis of functional monomer building blocks, to permit consistency and optimization of these processes. Herein we present a general emulsion polymerization method for synthesis of a copolymer consisting of three functional monomers, suitable for adaptation to alternate base chemistries, curing chemistries, and functional ligands. This protocol includes the synthesis of the functional monomers glycidyl methacrylate-iminodiacetic acid (GMA-IDA) and 4-benzolylphneyl methacrylate (BPM). Our synthesized copolymer includes a glycidyl methacrylate (GMA) monomer functionalized with a metal-chelating iminodiacetic acid (IDA) ligand, a UV-curable monomer, 4-benzoylphenyl methacrylate (BPM), and an inert hydrophobic monomer, n‑ butyl acrylate (BA). The presented synthesis route demonstrates a general polymerization method that can be modified to copolymerize alternative functional monomers to create multi-functional polymers.

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Photo‐Curable Metal‐Chelating Coatings Offer a Scalable Approach to Production of Antioxidant Active Packaging

Cited by 30 publications

References 52 publications

Antioxidant functionalization of biomaterials via reactive extrusion

Antioxidant functionalization of biomaterials via reactive extrusion

Synthesis, physicochemical properties, and health aspects of structured lipids: A review

General method for emulsion polymerization to yield functional terpolymers

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