Ultrahigh oxygen-scavenging norbornene copolymers bearing imidazolyl iron complexes for fabricating active and sustainable packaging films

Wang, Yu; Hasegawa, Yui; Serikawa, Takuma; Oyaizu, Kenichi; Nishide, Hiroyuki

doi:10.1039/c9cc08788e

Cited by 3 publications

(1 citation statement)

References 26 publications

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“…This study is based on the idea that functionalization of nonpolar polynorbornene with blocks of Et–VOAc and Et–VOH copolymers can expand the area of its possible application, and in particular can improve the properties of polynorbornene coatings by increasing their gas barrier characteristics. It is worth noting that polynorbornenes were used as matrices for oxygen barrier materials [ 24 , 25 ]. In this paper, we begin with the synthesis of multiblock copolymers from polynorbornene and poly(5-acetoxy-1-octenylene) via the cross-metathesis reaction.…”

Section: Introductionmentioning

confidence: 99%

Olefin-Metathesis-Derived Norbornene–Ethylene–Vinyl Acetate/Vinyl Alcohol Multiblock Copolymers: Impact of the Copolymer Structure on the Gas Permeation Properties

et al. 2022

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Commercial metathesis polynorbornene is used for the fabrication of high-damping coatings and bulk materials that dissipate vibration and impact energies. Functionalization of this non-polar polymer can improve its adhesive, gas barrier, and other properties, thereby potentially expanding its application area. With this aim, the post-modification of polynorbornene was carried out by inserting ethylene–vinyl acetate–vinyl alcohol blocks into its backbone via the cross-metathesis of polynorbornene with poly(5-acetoxy-1-octenylene) and subsequent deacetylation and hydrogenation of the obtained multiblock copolymers. For the first time, epoxy groups were introduced into the main chains of these copolymers, followed by the oxirane ring opening reaction. The influence of post-modification on the thermal, gas separation, and mechanical properties of the new copolymers was studied. It was shown that the gas permeability of the copolymer significantly depends on its composition, as well as on the amounts of hydroxyl and epoxy groups. The developed methods efficiently improve the barrier properties, reducing the oxygen permeability by 15–33 times in comparison with polynorbornene. The obtained results are promising for various applications and can be extended to a broader family of polydienes and other polymers containing backbone double bonds.

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Section: Introductionmentioning

confidence: 99%

Olefin-Metathesis-Derived Norbornene–Ethylene–Vinyl Acetate/Vinyl Alcohol Multiblock Copolymers: Impact of the Copolymer Structure on the Gas Permeation Properties

et al. 2022

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Substituted polynorbornene membranes: a modular template for targeted gas separations

et al. 2021

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Allylic hydrocarbon polymers complexed with Fe(II)(salen) as a ultrahigh oxygen-scavenging and active packaging film

Wang

Oyaizu

Nishide

2020

Pure and Applied Chemistry

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Macromolecular metal complexes provide a molecular-based synergy function of organic polymers and combined metal complexes. A new category of macromolecular complexes includes catalytically active metal complexes immobilized by organic polymers containing reactive substrate moieties in their repeating units. Here, we describe the extremely efficient oxidation of allylic hydrocarbon polymers with the attached iron complex catalyst, as well as the efficient oxygen-consumption or oxygen-scavenging function of the matrix polymer film. The less toxic N,N´-di(salicylaldehyde)ethylenediiminatoiron(II) complex was combined with or fixed onto a series of allylic hydrocarbon polymers as both the oxidative substrate and the film matrix, i.e. poly(1,2-butadiene), polynorbornene, poly(5-vinyl-2-norbornene), poly(2,5-norboenadiene), poly(dicyclopentadiene), and poly(5-ethylidene-2-norbornene). Ultra-high oxygen-scavenging capacity up to 300 mL (oxygen gas at STP)/g(film) was achieved, based on the oxidative consumption of the allylic bond (particularly of poly(5-ethylidene-2-norbornene)), which was more than three times that of the previously reported highest oxygen-scavenging polymers. These oxygen-scavenging films are based on the high reactivity of polymer-metal complexes that provides an innovative development in the area of active packaging polymer films that facilitate cost-effective performance, safety, and sustainability.

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Ultrahigh oxygen-scavenging norbornene copolymers bearing imidazolyl iron complexes for fabricating active and sustainable packaging films

Abstract: A tough and transparent polynorbornene film affixing an iron–salen catalyst exhibited an ultra-high oxygen-scavenging capacity up to 300 mL g−1.

Cited by 3 publications

References 26 publications

Olefin-Metathesis-Derived Norbornene–Ethylene–Vinyl Acetate/Vinyl Alcohol Multiblock Copolymers: Impact of the Copolymer Structure on the Gas Permeation Properties

Olefin-Metathesis-Derived Norbornene–Ethylene–Vinyl Acetate/Vinyl Alcohol Multiblock Copolymers: Impact of the Copolymer Structure on the Gas Permeation Properties

Substituted polynorbornene membranes: a modular template for targeted gas separations

Allylic hydrocarbon polymers complexed with Fe(II)(salen) as a ultrahigh oxygen-scavenging and active packaging film

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