Polymerization-crosslinking of renewable itaconic acid in water and in deep eutectic solvents

Bednarz, Szczepan; Półćwiartek, Katarzyna; Wityk, Joanna; Strachota, Beata; Kredatusová, Jana; Beneš, Hynek; Wesołowska-Piętak, Angelika; Kowalski, Grzegorz

doi:10.1016/j.eurpolymj.2017.08.020

Cited by 36 publications

(26 citation statements)

References 58 publications

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“…That is why, some research groups use it in polymerization reactions in combination with DESs, where it serves as HBD. A number of publications have reported the use of itaconic acid, along with choline chloride or tetraethylammonium chloride, in free-radical polymerization [64,67,70,71,72].…”

Section: Research On Polymerization In Deep Eutectic Solventsmentioning

confidence: 99%

“…As a result, the formation of xerogels, with the yield of the gel fraction of 29‒100% for the systems without poly(ethyleneglycol), and of 64, 74% for the systems containing poly(ethyleneglycol), was observed. The following year, Bednarz et al reported on the formation of polymeric products at pre- (nanogel-like networks) and post-gel stages (macrogels) [72].…”

Section: Research On Polymerization In Deep Eutectic Solventsmentioning

confidence: 99%

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Use of Deep Eutectic Solvents in Polymer Chemistry–A Review

2019

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This review deals with two overlapping issues, namely polymer chemistry and deep eutectic solvents (DESs). With regard to polymers, specific aspects of synthetic polymers, polymerization processes producing such polymers, and natural cellulose-based nanopolymers are evaluated. As for DESs, their compliance with green chemistry requirements, their basic properties and involvement in polymer chemistry are discussed. In addition to reviewing the state-of-the-art for selected kinds of polymers, the paper reveals further possibilities in the employment of DESs in polymer chemistry. As an example, the significance of DES polarity and polymer polarity to control polymerization processes, modify polymer properties, and synthesize polymers with a specific structure and behavior, is emphasized.

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Section: Research On Polymerization In Deep Eutectic Solventsmentioning

confidence: 99%

Section: Research On Polymerization In Deep Eutectic Solventsmentioning

confidence: 99%

Use of Deep Eutectic Solvents in Polymer Chemistry–A Review

2019

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“…The acid is also a well‐known low reactive vinyl monomer, and its free radical polymerization typically requires long reaction times and high amounts of an initiator . Based on our previous experience with persulphate‐initiated polymerization of the acid in aqueous media and in choline‐based DESs, we have asked ourselves whether it would be possible to prepare itaconic polymers via initiator‐free radical polymerization. It is well known that spontaneous thermal radical polymerization at temperature >100 °C is possible for several reactive vinyl monomers, including styrene and acrylic monomers .…”

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confidence: 99%

High‐Molecular‐Weight Polyampholytes Synthesized via Daylight‐Induced, Initiator‐Free Radical Polymerization of Renewable Itaconic Acid

Mielczarek

Łabanowska

Kurdziel

et al. 2020

Macromol. Rapid Commun.

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Herein, it is reported for the first time that when mixed with choline chloride, itaconic acid (IA), normally a low‐reactive vinyl monomer, undergoes initiator‐free radical polymerization under normal daylight. Furthermore, the process results in the formation of abnormally high‐molecular‐weight poly(itaconic acid) derivatives with Mw greater than ≈800 000 g mol−1. Detailed 1D/2D NMR studies indicate that the polymers have two types of ionizable moieties, that is, anionic carboxylic and cationic choline ester groups in an average molar ratio of 12:1. Potentiometric titration shows polyampholyte behavior of the polymers. Tentative mechanistic studies reveal that the daylight‐induced polymerization is initiated by species generated via interactions of near UV light with IA. However, EPR findings show that choline also participates in secondary radical reactions. The obtained polyampholytes are useful bio‐based materials for fast and straightforward fabrication of polymer–clay nanocomposite hydrogels with excellent mechanical properties.

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“…Several examples of gels prepared from polymerizable eutectics have been reported. Bednarz et al [ 101 , 102 ] used a 1:1 itaconic acid (IA):ChCl DES to prepare cross-linked poly(itaconic acid– co – N,N’ -methylenebisacrylamide (BIS)) hydrogels. A comparative study for gel synthesis in water was performed using potassium persulfate (KPS) as initiator at 65 °C, which proceeded to completion within 2 h in the eutectic, but only ~50% conversion in water.…”

Section: Des Systems In Polymer and Materials Sciencementioning

confidence: 99%

Greener, Faster, Stronger: The Benefits of Deep Eutectic Solvents in Polymer and Materials Science

2021

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Deep eutectic solvents (DESs) represent an emergent class of green designer solvents that find numerous applications in different aspects of chemical synthesis. A particularly appealing aspect of DES systems is their simplicity of preparation, combined with inexpensive, readily available starting materials to yield solvents with appealing properties (negligible volatility, non-flammability and high solvation capacity). In the context of polymer science, DES systems not only offer an appealing route towards replacing hazardous volatile organic solvents (VOCs), but can serve multiple roles including those of solvent, monomer and templating agent—so called “polymerizable eutectics.” In this review, we look at DES systems and polymerizable eutectics and their application in polymer materials synthesis, including various mechanisms of polymer formation, hydrogel design, porous monoliths, and molecularly imprinted polymers. We provide a comparative study of these systems alongside traditional synthetic approaches, highlighting not only the benefit of replacing VOCs from the perspective of environmental sustainability, but also the materials advantage with respect to mechanical and thermal properties of the polymers formed.

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Polymerization-crosslinking of renewable itaconic acid in water and in deep eutectic solvents

Cited by 36 publications

References 58 publications

Use of Deep Eutectic Solvents in Polymer Chemistry–A Review

Use of Deep Eutectic Solvents in Polymer Chemistry–A Review

High‐Molecular‐Weight Polyampholytes Synthesized via Daylight‐Induced, Initiator‐Free Radical Polymerization of Renewable Itaconic Acid

Greener, Faster, Stronger: The Benefits of Deep Eutectic Solvents in Polymer and Materials Science

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