Synthesis, characterization, and computational study of potential itaconimide-based initiators for atom transfer radical polymerization

Deoghare, Chetana; Baby, C.; Nadkarni, Vishnu S.; Behera, Raghu Nath; Chauhan, Rashmi

doi:10.1039/c4ra08981b

Cited by 12 publications

(9 citation statements)

References 86 publications

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“…To obtain an ATRP initiator that is optimized for itaconimides, [ N ‐phenyl(3‐bromo‐3‐methyl)succinimide, N ‐phenyl(3‐bromo‐4‐methyl)succinimide, and N ‐phenyl(3‐bromomethyl)succinimide] were synthesized ( Figure a). [ 124 ] The N ‐phenyl(3‐bromo‐3‐methyl)succinimide initiator was used to synthesize copolymers of N ‐phenylitaconimide and MMA (Figure 3b). AGET‐ATRP conditions were used.…”

Section: Controlled Radical Polymerization Of Itaconic Acid and Its Dmentioning

confidence: 99%

“…The resulting copolymers had a linear increase of M n with conversion, indicating that the reaction was well controlled, even to near‐quantitative conversion (Figure 3c). [ 124 ] The obtained M n was 13 200 g mol −1 , with a PDI of 1.3, which was better than the reaction control obtained with the commercially available ATRP initiator ethyl‐α‐bromoisobutyrate (EBiB). [ 124 ] In the same study, structural and thermodynamic properties of these initiators were modeled by density functional theory (DFT).…”

Section: Controlled Radical Polymerization Of Itaconic Acid and Its Dmentioning

confidence: 99%

“…[ 124 ] The obtained M n was 13 200 g mol −1 , with a PDI of 1.3, which was better than the reaction control obtained with the commercially available ATRP initiator ethyl‐α‐bromoisobutyrate (EBiB). [ 124 ] In the same study, structural and thermodynamic properties of these initiators were modeled by density functional theory (DFT). [ 124 ] In a study where the entire polymerization process was modelled by DFT, and the modeled polymer tacticity matched the experimentally determined one.…”

Section: Controlled Radical Polymerization Of Itaconic Acid and Its Dmentioning

confidence: 99%

“…[ 124 ] In the same study, structural and thermodynamic properties of these initiators were modeled by density functional theory (DFT). [ 124 ] In a study where the entire polymerization process was modelled by DFT, and the modeled polymer tacticity matched the experimentally determined one. [ 125,126 ] Further, copolymers of N ‐(4‐chlorophenyl)itaconimide, N ‐phenylitaconimide, and N ‐(4‐methoxyphenyl)itaconimide with MMA were synthesized by ATRP (CuBr/Bby/EBiB, in anisol at 80 °C) with 20 to 30 mol% itaconimide content.…”

Section: Controlled Radical Polymerization Of Itaconic Acid and Its Dmentioning

confidence: 99%

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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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Section: Controlled Radical Polymerization Of Itaconic Acid and Its Dmentioning

confidence: 99%

Section: Controlled Radical Polymerization Of Itaconic Acid and Its Dmentioning

confidence: 99%

Section: Controlled Radical Polymerization Of Itaconic Acid and Its Dmentioning

confidence: 99%

Section: Controlled Radical Polymerization Of Itaconic Acid and Its Dmentioning

confidence: 99%

See 2 more Smart Citations

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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“…itaconic, 52 citraconic, 36,37 or dimethylmaleic anhydrides 39 ; phenylisocyanide 53,54 ; or phenyliminovinylidenphosphoran. 51 Scheme 1 Present work.…”

Section: Introductionmentioning

confidence: 99%

One-step Barton decarboxylation by micellar catalysis – application to the synthesis of maleimide derivatives

2015

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Maleimides being studied or used in various applications, for the first time, a facile entry to Barton decarboxylation in aqueous media is described to obtain in one step substituted N-phenylmaleimide synthons. The radicals, generated by the ultrasonic lysis of N-hydroxy-2-thiopyridone esters, reacted respectively with electron deficient olefin phenylmaleimide in a one-step radical addition. These esters were obtained from natural fatty acid derivatives including unsaturated ones. Various activating conditions (UV, sonication, heating, microwaves), reactants and solvent adjustment, as well as surfactants were tested to improve the yield of the reaction. One of the products obtained was then transformed into a new electron-trap monosubstituted maleimide and was able to react again to obtain a disubstituted N-phenylmaleimide derived from biomass.

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RDRP (Meth)acrylic Homo and Block Polymers from Lignocellulosic Sugar Derivatives

Palà

Woods

Hatton

et al. 2022

Macro Chemistry & Physics

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Currently, most commodity chemicals and polymers are manufactured from nonrenewable petroleum-based resources. However, due to its finite nature and social claims about environment preservation, alternative sources of value-added and building block chemicals are being intensively studied. Renewable lignocellulosic biomass has offered an attractive replacement for fossil-based chemicals. Lignin and C5/C6 sugars obtained from lignocellulosic biomass through chemical and enzymatic methods can be further transformed to targeted chemical platforms. In the present review, synthetic pathways for well-defined poly(meth)acrylates obtained from C5/C6 sugar-derived platforms in which the sugar structure is not retained are discussed. While bio-based polymers from these monomers are investigated using a wide range of polymerization techniques, this study focuses on precise synthesis of macromolecular structures taking advantage of reversible-deactivation radical polymerization methods and their applications.

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Synthesis, characterization, and computational study of potential itaconimide-based initiators for atom transfer radical polymerization

Abstract: We report synthesis of potential initiators1a-Br,2a-Br, and3a-Br for the ATRP ofN-phenylitaconimide and MMA. We find (i) good agreement between experimentally determined and calculatedKATRPvalues (ii)3a-Br performs better than the commercially available initiator.

Cited by 12 publications

References 86 publications

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

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

One-step Barton decarboxylation by micellar catalysis – application to the synthesis of maleimide derivatives

RDRP (Meth)acrylic Homo and Block Polymers from Lignocellulosic Sugar Derivatives

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