Recent advances in RAFT polymerization of monomers derived from renewable resources

Hatton, Fiona L.

doi:10.1039/c9py01128e

Cited by 55 publications

(51 citation statements)

References 67 publications

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“…With great urgency, the social responsibility of polymer chemists to address the intensifying issue of plastic pollution must also be acknowledged. In this regard, progress with sustainable sources of vinyl monomers, [ 175,176 ] and building‐in degradability into vinyl polymers should take precedence. [ 177 ] Parallel progress in machine learning and automated synthetic chemistry will also inevitably impact the study of RAFT.…”

Section: Future Outlookmentioning

confidence: 99%

Progress and Perspectives Beyond Traditional RAFT Polymerization

et al. 2020

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The development of advanced materials based on well-defined polymeric architectures is proving to be a highly prosperous research direction across both industry and academia. Controlled radical polymerization techniques are receiving unprecedented attention, with reversible-deactivation chain growth procedures now routinely leveraged to prepare exquisitely precise polymer products. Reversible addition-fragmentation chain transfer (RAFT) polymerization is a powerful protocol within this domain, where the unique chemistry of thiocarbonylthio (TCT) compounds can be harnessed to control radical chain growth of vinyl polymers. With the intense recent focus on RAFT, new strategies for initiation and external control have emerged that are paving the way for preparing well-defined polymers for demanding applications. In this work, the cutting-edge innovations in RAFT that are opening up this technique to a broader suite of materials researchers are explored. Emerging strategies for activating TCTs are surveyed, which are providing access into traditionally challenging environments for reversible-deactivation radical polymerization. The latest advances and future perspectives in applying RAFT-derived polymers are also shared, with the goal to convey the rich potential of RAFT for an ever-expanding range of high-performance applications.

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Section: Future Outlookmentioning

confidence: 99%

Progress and Perspectives Beyond Traditional RAFT Polymerization

et al. 2020

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“…[ 320–323 ] Hatton also recently covered its application to biobased monomers. [ 24 ] Applied to various (meth)acrylic and styrenic monomers, RAFT polymerization exhibits living characteristics and proceeds via a degenerative transfer of growing polymer chains ( Figure ). Various chain transfer agents (CTAs) have been developed for RAFT polymerization, the most common being dithiobenzoates and trithiocarbonates.…”

Section: Polymerization Of (Meth)acrylic Monomers and Analogsmentioning

confidence: 99%

“…The objective of the present review is therefore to provide an overview of the different methodologies and strategies that have been employed to synthesize acrylates and analogs from bioresources. In order to avoid duplicity with existing literature, [ 16–25 ] herein, we will focus on the path from renewable feedstocks to the vinylic moiety of the biobased monomers ( Figure ) and the multiple molecular structures that have been obtained by different synthetic routes. We will also emphasize important advances in the polymerization of these monomers.…”

Section: Introductionmentioning

confidence: 99%

Production and Polymerization of Biobased Acrylates and Analogs

Fouilloux

Thomas

2021

Macromol. Rapid Commun.

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To prepare biobased polymers, particular attention must be paid to the obtention of the monomers from which they are derived. (Meth)acrylates and their analogs constitute such a class of monomers that have been extensively studied due to the wide range of polymers accessible from them. This review therefore aims to highlight the progresses made in the production and polymerization of (meth)acrylates and their analogs. Acrylic acid production from biomass is close to commercialization, as three different high‐potential intermediates are identified: glycerol, lactic acid, and 3‐hydroxypropionic acid. Biobased methacrylic acid is less common, but several promising options are available, such as the decarboxylation of itaconic acid or the dehydration of 2‐hydroxyisobutyric acid. Itaconic acid is also a vinylic monomer of great interest, and polymers derived from it have already found commercial applications. Methylene butyrolactones are promising monomers, obtained from bioresources via three different intermediates: levulinic, succinic, or itaconic acid. Although expensive, methylene butyrolactones have a strong potential for the production of high‐performance polymers. Finally, β‐substituted acrylic monomers, such as cinnamic, fumaric, muconic, or crotonic acid, are also examined, as they provide an original access to biobased materials from various renewable raw materials, such as protein waste, lignin, or wastewater.

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“…In the context of improving product sustainability, itaconic acid (2‐methylene butane‐1,4‐dicarboxylic acid) is lately receiving increased attention. [ 1–3 ] Itaconic acid and some of its derivatives are industrially important co‐monomers used in the synthesis of methacrylate‐ and acrylate‐based copolymers by free radical polymerizations (FRP). Depending on their exact structure and composition, these copolymers can be anything from water‐soluble to rock‐solid.…”

Section: Introduction and Scopementioning

confidence: 99%

Progress in the Free and Controlled Radical Homo‐ and Co‐Polymerization of Itaconic Acid Derivatives: Toward Functional Polymers with Controlled Molar Mass Distribution and Architecture

Sollka

Lienkamp

2020

Macromol. Rapid Commun.

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Polymeric derivatives of itaconic acid are becoming increasingly more interesting for research and industry because itaconic acid is accessible from renewable resources. In spite of the structural similarity of poly(itaconic acid derivatives) to poly(methacrylates), they are much less reactive, homopolymerize only sluggishly by free radical polymerization (FRP), and are often obtained with low molar masses and conversions. This has so far limited their use. The reasons for the low reactivity of itaconic acid derivatives (including itaconimides, diitaconates, and diitaconamides) are combined steric and electronic effects, as demonstrated by the body of literature on the FRP homopolymerization kinetics of these monomers which is summarized herein. These problems can be solved to a large extent by using controlled radical polymerization (CRP) techniques, notably atom transfer radical polymerization (ATRP) and reversible addition and fragmentation chain transfer radical polymerization (RAFT). By optimizing the reaction conditions for the ATRP and RAFT of itaconic acid derivatives, in particular the reaction temperature, linear relations between molar mass and conversion are obtained in many cases, and homopolymers with high molar masses and reasonably narrow polydispersity indices become accessible. This review presents the state‐of‐the‐art FRP and CRP of itaconic acid derivatives, and highlights functional polymers obtained by these methods.

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Recent advances in RAFT polymerization of monomers derived from renewable resources

Abstract: In this Minireview, RAFT polymerization of monomers derived from renewable resources is explored. Methods used to prepare these monomers are discussed, and potential applications of the resulting renewable polymers are highlighted.

Cited by 55 publications

References 67 publications

Progress and Perspectives Beyond Traditional RAFT Polymerization

Progress and Perspectives Beyond Traditional RAFT Polymerization

Production and Polymerization of Biobased Acrylates and Analogs

Progress in the Free and Controlled Radical Homo‐ and Co‐Polymerization of Itaconic Acid Derivatives: Toward Functional Polymers with Controlled Molar Mass Distribution and Architecture

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