Microwave‐assisted nitroxide‐mediated radical polymerization of acrylamide in aqueous solution

Rigolini, Julien; Grassl, Bruno; Billon, Laurent; Reynaud, Stéphanie; Donard, O. F. X.

doi:10.1002/pola.23731

Cited by 45 publications

(37 citation statements)

References 48 publications

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“…The same group polymerized acrylamide in water employing a similar initiating system in microwave-assisted NMP. 10 Charleux's group 11 performed nitroxide-mediated copolymerization of methacrylic acid (MA) and sodium 4-styrenesulfonate in acidic conditions (pH = 3.5) in water using the BlocBuilder alkoxyamine and SG1 at a comparatively low temperature (76°C). The short polymerization time and low temperature were considered important parameters in enabling the successful NMP even at low pH.…”

Section: ■ Introductionmentioning

confidence: 99%

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Nitroxide-Mediated Polymerization of 2-(Diethylamino)ethyl Methacrylate (DEAEMA) in Water

et al. 2014

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Nitroxide-mediated polymerization (NMP) of 2-(diethylamino)ethyl methacrylate (DEAEMA) with a small amount of acrylonitrile (AN) as a comonomer was performed for the first time in water at 90°C and atmospheric pressure using n-hydroxysuccinimidyl BlocBuilder (NHS-BB) alkoxyamine without addition of excess nitroxide. The same reaction was carried out using the bicomponent initiating system composed of 2,2′-azobis[2-(2-imidazolin-2-yl)propane]-dihydrochloride (VA-044) as initiator and N-tert-butyl-N-(1-diethylphosphono-2,2-dimethylpropyl) nitroxide (SG1) as nitroxide. Both polymerization reactions were well-controlled and exhibited excellent livingness as evidenced by low molar dispersity and evolution of the molar mass distribution. The hydrolytic stability of DEAEMA at the polymerization conditions and the effects of several parameters including initiating system, temperature, ratio of nitroxide to initiator, initiator and monomer concentrations, and comonomer type were investigated. Chain extension of the synthesized macroinitiator with methyl methacrylate (MMA) and styrene (S) in a one-pot process led to the in situ formation of poly(DEAEMA-co-S)-b-poly(MMA-co-S) diblock copolymers based on the polymerization-induced self-assembly (PISA) process. ■ INTRODUCTIONDevelopment of controlled/living radical polymerization (LRP) has had a major impact on polymer science. 1−3 (The new terminology of reversible deactivation radical polymerization (RDRP) has been proposed by IUPAC for LRP. 4 ) Polymeric architectures with different composition, structures, and functionalities can be prepared in relatively mild conditions by LRP techniques. Of the three main types of LRPs, nitroxidemediated polymerization (NMP) and atom-transfer radical polymerization (ATRP) are based on reversible activation− deactivation cycles of growing polymer chains while reversible addition−fragmentation transfer (RAFT) polymerization is based on reversible chain transfer. 3 NMP is a powerful technique with arguably the simplest mechanisms among all LRP techniques for preparing polymers with a narrow molecular weight distribution (MWD) and low molar dispersity (Đ). 5 Furthermore, there is no concern of residual catalyst, color, or toxicity in the final polymer. LRP can be applied for the preparation of well-defined polymeric architectures in aqueous media which is not possible in ionic polymerization. 1 However, applying LRP in aqueous media (homogeneous or dispersed) is often quite difficult due to problems such as hydrolysis and aminolysis reactions in RAFT polymerization or other side reactions in the case of ATRP. 6,7 There are a very limited number of reports related to NMP in homogeneous aqueous solution. A further difficulty for NMP is the high temperature (>100°C) traditionally required which necessitates using pressurized vessels. However, performing NMP at lower temperatures now is possible with some nitroxide/ monomer combinations. The first example of NMP conducted in homogeneous aqueous solution was with of sodium 4-styrenesulfonate in ...

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Section: ■ Introductionmentioning

confidence: 99%

“…The same group polymerized acrylamide in water employing a similar initiating system in microwave-assisted NMP. 10 …”

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confidence: 97%

Nitroxide-Mediated Polymerization of 2-(Diethylamino)ethyl Methacrylate (DEAEMA) in Water

et al. 2014

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“…To date, NMP has been extended to almost all monomers with the exception of vinyl esters and vinyl chloride. Also, SG1 and SG1-derived initiators (essentially BlocBuilder MA) have been applied to the polymerization of acrylamide- [234][235][236], styrenic- [234], acrylate- [234] and methacrylate-monomers [233,237], directly in homogeneous aqueous solution. Nevertheless, the use of a small fraction of comonomer (typically 8% of acrylonitrile for methacrylates, or sodium 4-styrenesulfonate for methacrylic acid) proved essential for the system to work at T < 100 °C and even then the dispersity index was systematically higher than 1.20.…”

Section: Discussionmentioning

confidence: 99%

Synthesis of Glycopolymer Architectures by Reversible-Deactivation Radical Polymerization

Ghadban

Albertin

2013

Polymers

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This review summarizes the state of the art in the synthesis of well-defined glycopolymers by Reversible-Deactivation Radical Polymerization (RDRP) from its inception in 1998 until August 2012. Glycopolymers architectures have been successfully synthesized with four major RDRP techniques: Nitroxide-mediated radical polymerization (NMP), cyanoxyl-mediated radical polymerization (CMRP), atom transfer radical polymerization (ATRP) and reversible addition-fragmentation chain transfer (RAFT) polymerization. Over 140 publications were analyzed and their results summarized according to the technique used and the type of monomer(s) and carbohydrates involved. Particular emphasis was placed on the experimental conditions used, the structure obtained (comonomer distribution, topology), the degree of control achieved and the (potential) applications sought. A list of representative examples for each polymerization process can be found in tables placed at the beginning of each section covering a particular RDRP technique.

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“…Conversely, Zhang and Schubert reported that the ATRP of MMA with CuBr or CuCl / N-hexy 1-2-py ridy Imethy nimine / ethyl 2-bromoisobutyrate in solution of p-xylene showed no increase in polymerization rate when performed under MW conditions. Leenen et al could successfully perform the NMP of methyl acrylate and tert-butyl acrylate at 120°C in a solution of dioxan under MW conditions [90]. Nicolay et al and Phan et al demonstrated that NMP in homogeneous aqueous solution was possible below the boiling point of water by using second-generation nitroxides, namely N-tert-butyl-N-(l-diethylphosphono-2,2-imethylpropyl)nitroxide [90][91][92].…”

Section: Controlled Radical Polymerizationmentioning

confidence: 99%

Green Polymer Synthesis: An Overview on Use of Microwave‐Irradiation

Mishra

Dubey

2011

Green Chemistry for Environmental Remediation

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Microwave‐assisted nitroxide‐mediated radical polymerization of acrylamide in aqueous solution

Cited by 45 publications

References 48 publications

Nitroxide-Mediated Polymerization of 2-(Diethylamino)ethyl Methacrylate (DEAEMA) in Water

Nitroxide-Mediated Polymerization of 2-(Diethylamino)ethyl Methacrylate (DEAEMA) in Water

Synthesis of Glycopolymer Architectures by Reversible-Deactivation Radical Polymerization

Green Polymer Synthesis: An Overview on Use of Microwave‐Irradiation

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