Bio‐ and Water‐Based Reversible Covalent Bonds Containing Polymers (Vitrimers) and Their Relevance to Adhesives – A Critical Review

Jarach, Natanel; Zuckerman, Racheli; Naveh, Naum; Dodiuk, H.; Kenig, S.

doi:10.1002/9781119846703.ch13

Cited by 7 publications

(8 citation statements)

References 114 publications

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“…Reversible covalent-bond-containing polymers (RCBPs), also known as vitrimers, covalent adaptable networks (CANs), or reorganizable polymers, are a new class of polymers that share a three-dimensional (3D) network-like structure with thermosets while having reprocessability and recyclability due to their dynamic or reversible cross-links. − Among the reversible bonds studied in the literature, [2 + 2] and [4 + 4] cycloadditions are unique in having potential use in irradiation-based applications, such as photocuring of adhesives and stereolithography-based 3D printing. This potential results from the adduct formation under irradiation at specific wavelengths and dissociation under shorter ones .…”

Section: Introductionmentioning

confidence: 99%

Tetra-Dentate Cycloaddition Catalysts for Rapid Photopolymerization Reactions

et al. 2023

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Metrics & MoreArticle Recommendations * sı Supporting InformationABSTRACT: [4 + 4] and [2 + 2] cycloadditions are unique reactions since they form and deform cycloadducts under irradiation due to their inherent reversible nature. Whereas promising for the field of recycling, these reactions usually suffer from two major shortcomings: long reaction durations (hours) and the requirement of high-intensity light (∼100 W/cm 2 ), typically at a short wavelength (<330 nm). We demonstrate several tetra-dentate catalysts that can overcome these fundamental limitations. Among them is a tin complex that enables 76% conversion within only 2 min of irradiation at 395 nm, much faster than the known ruthenium-based catalyst, under irradiation with light intensity two orders of magnitude lower than that reported in the literature. Due to the short photopolymerization time, low intensity (27 mW/cm 2 ), and long UV light (395 nm), this unique complex opens new avenues for recycling three-dimensional printing products based on photopolymerization of cycloaddition reactions.

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Section: Introductionmentioning

confidence: 99%

Tetra-Dentate Cycloaddition Catalysts for Rapid Photopolymerization Reactions

et al. 2023

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“…As a result, these networks possess ideal properties to be used in applications such as soft robotics 20 or reversible adhesives. 21 However, when used in commercial applications, additional information on the stability of the networks is required, but this has not yet been investigated for these networks.…”

Section: ■ Introductionmentioning

confidence: 99%

“…The networks showed, besides promising healing and recycling properties, improved thermal and mechanical properties directly related to the lignin incorporation. As a result, these networks possess ideal properties to be used in applications such as soft robotics or reversible adhesives . However, when used in commercial applications, additional information on the stability of the networks is required, but this has not yet been investigated for these networks.…”

Section: Introductionmentioning

confidence: 99%

Bioaromatic-Associated Multifunctionality in Lignin-Containing Reversible Elastomers

Thys

Kaya

Soetemans

et al. 2023

ACS Appl. Polym. Mater.

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The unique molecular structure of lignin, intrinsically rich in bioaromatic groups (phenolic hydroxyls), gives it, e.g., antioxidant, antistatic, antimicrobial, UV-blocking, hydrophobic, or even flame-retardant properties, which are highly interesting. An attractive strategy to use lignin as a macro-monomer for the design of functional materials that retain certain of these lignin-specific properties is to partially preserve some phenolic groups during the synthesis. In this work, we explore the properties of reversible elastomers containing a lignin fraction whose phenolic groups have only been partially modified. To do so, Kraft lignin was first fractionated and partially (89%) modified with furan groups, allowing its homogeneous incorporation in Diels–Alder formulations. The effect of the residual phenolic groups embedded in the polymer matrix was then systematically studied, focusing on the specific material properties associated with lignin. The obtained lignin-containing networks notably showed increased radical scavenging activity (which directly resulted in improved antistatic and antioxidant properties), displayed improved UV absorbance due to the presence of multiple lignin chromophores, and were even able to inhibit the growth of bacteria. This article demonstrates that tailored and partially modified lignin fractions could be used as multi-functional building blocks for the design of complex (and reversible) polymer architectures, mimicking some of the unique lignin functionalities found in nature, and this without the need to add specific additives.

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“…[ 4,5 ] and Li et al., [ 6 ] or require high temperatures for a long time, sometimes even hours, during (re) printing (120–200 °C). [ 1,3,7 ] This limits the number of recycling cycles due to degradation of the printed polymer or due to irreversible side reactions, as well as high energy consumption during the recycling and reprinting processes.…”

Section: Introductionmentioning

confidence: 99%

“…Such materials incorporate dynamic and reversible bonds; thus, they can be processed despite their network structure composed of cross-linked polymers (thermosets). [1][2][3] In general, RCBPs are divided into two types of bonds: dynamic bonds, also known as associative CANs, and general bonds, also known as dissociative CANs. [1] Dynamic bonds, like the thermal-triggered transesterification of 𝛽-hydroxy esters, react to a similar factor to form or break the bonds.…”

Section: Introductionmentioning

confidence: 99%

Fully Recyclable Cured Polymers for Sustainable 3D Printing

Jarach,

Dodiuk,

Kenig

et al. 2023

Advanced Materials

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The most prevalent materials used in the Additive Manufacturing era are polymers and plastics. Unfortunately, these materials are recognized for their negative environmental impact as they are primarily non‐recyclable, resulting in environmental pollution. In recent years, a new sustainable alternative to these materials has been emerging: reversible covalent bond‐containing polymers (RCBPs). These materials can be recycled, reprocessed, and reused multiple times without losing their properties. Nonetheless, they have two significant drawbacks when used in 3D printing. First, some require adding new materials every reprinting cycle, and second, others require high temperatures for (re)printing, limiting recyclability and increasing energy consumption. This study, thus, introduces fully recyclable RCBPs as a sustainable approach for radiation‐based printing technologies. This approach enables multiple (re)printing cycles at low temperatures (50 °C lower than the lowest reported) without adding new materials. It involves purposefully synthesized polymers that undergo reversible photopolymerization, composed of a tin‐based catalyst. An everyday microwave oven quickly de‐polymerized these polymers, obtaining complete reversibility.This article is protected by copyright. All rights reserved

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Bio‐ and Water‐Based Reversible Covalent Bonds Containing Polymers (Vitrimers) and Their Relevance to Adhesives – A Critical Review

Cited by 7 publications

References 114 publications

Tetra-Dentate Cycloaddition Catalysts for Rapid Photopolymerization Reactions

Tetra-Dentate Cycloaddition Catalysts for Rapid Photopolymerization Reactions

Bioaromatic-Associated Multifunctionality in Lignin-Containing Reversible Elastomers

Fully Recyclable Cured Polymers for Sustainable 3D Printing

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