Phosphonated Polyethyleneimines (PEIP) as Multi-Use Polymers

Villemin, Didier; Monteil, C.; Bar, Nathalie; Didi, Mohamed Amine

doi:10.1080/10426507.2014.981633

Cited by 12 publications

(14 citation statements)

References 37 publications

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“…The Moedritzer–Irani reaction was also applied to introduce phosphonic acid functions on polymer or dendrimers possessing reactive amine. Accordingly, phosphonic acids were introduced on polyethyleneglycol 113 [ 188 ], polyethylene imine 114 [ 224 ] or chitosan 115 [ 225 ]. The functionalization of polyacrylamide obtained by reversible addition-fragmentation chain transfer (RAFT) polymerization was also recently reported to produce 116 ( Fig.…”

Section: Reviewmentioning

confidence: 99%

Phosphonic acid: preparation and applications

Sevrain¹,

Berchel²,

Couthon³

et al. 2017

Beilstein J. Org. Chem.

147

103

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The phosphonic acid functional group, which is characterized by a phosphorus atom bonded to three oxygen atoms (two hydroxy groups and one P=O double bond) and one carbon atom, is employed for many applications due to its structural analogy with the phosphate moiety or to its coordination or supramolecular properties. Phosphonic acids were used for their bioactive properties (drug, pro-drug), for bone targeting, for the design of supramolecular or hybrid materials, for the functionalization of surfaces, for analytical purposes, for medical imaging or as phosphoantigen. These applications are covering a large panel of research fields including chemistry, biology and physics thus making the synthesis of phosphonic acids a determinant question for numerous research projects. This review gives, first, an overview of the different fields of application of phosphonic acids that are illustrated with studies mainly selected over the last 20 years. Further, this review reports the different methods that can be used for the synthesis of phosphonic acids from dialkyl or diaryl phosphonate, from dichlorophosphine or dichlorophosphine oxide, from phosphonodiamide, or by oxidation of phosphinic acid. Direct methods that make use of phosphorous acid (H3PO3) and that produce a phosphonic acid functional group simultaneously to the formation of the P–C bond, are also surveyed. Among all these methods, the dealkylation of dialkyl phosphonates under either acidic conditions (HCl) or using the McKenna procedure (a two-step reaction that makes use of bromotrimethylsilane followed by methanolysis) constitute the best methods to prepare phosphonic acids.

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Section: Reviewmentioning

confidence: 99%

Phosphonic acid: preparation and applications

Sevrain¹,

Berchel²,

Couthon³

et al. 2017

Beilstein J. Org. Chem.

147

103

View full text Add to dashboard Cite

show abstract

“…Phosphorus-based resins were also reported as promising sorbents for Ag(I) in nitric acid solutions. Villemin et al [17] prepared phosphonate-polyethyleneimine resins (PEI), by controlled reaction of phosphorous acid with PEI, for preparing ionexchange resins and Ag-based antimicrobial polymers. A series of imidazole-based and polyamine resins was designed for the sorption of silver from HCl solutions [18]: imidazole-based resins reveal more efficient than polyamine-based resins.…”

Section: Introductionmentioning

confidence: 99%

2-Mercaptobenzimidazole derivative of chitosan for silver sorption – Contribution of magnetite incorporation and sonication effects on enhanced metal recovery

Elwakeel

Al‐Bogami

Guibal

2021

Chemical Engineering Journal

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“…Metal-chelating polymers have great potential in REE-extraction applications due to their low cost and high affinity for target elements. As a result, metal-chelating polymers are used in several current REE extraction and separation technologies such as ion-exchange resins, polymer-enhanced ultrafiltration, and macromolecular sorbants. − In addition, metal-chelating polymers can be tuned to have a high affinity for target elements by incorporating ligands that specifically chelate a desired metal. − REEs are hard Lewis acids; thus, these metals preferentially coordinate with hard Lewis basic ligands such as those with oxygen-donor atoms (e.g., amides, malonamides, and phosphine oxides). , In particular, phosphonate-containing polymers are often effective at binding REEs. − For example, branched poly(ethylenimine methylenephosphonate) (PEI-MP) has shown promise in several metal-chelation applications, including lanthanide/actinide separation, actinide exposure treatment, and internal radionuclide therapy. − …”

Section: Introductionmentioning

confidence: 99%

Synthesis and Rare-Earth-Element Chelation Properties of Linear Poly(ethylenimine methylenephosphonate)

et al. 2020

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Rare-earth elements (REEs) are indispensable for modern technology; consequently, effective materials for REE extraction and separation are in demand. Polymeric chelators polymers with metal binding functional groupsare often used in these applications due to their low cost and high selectivity for target ions, with phosphonate-containing polymers often proving particularly effective. We synthesized linear poly(ethylenimine methylenephosphonate), a material previously made only with a branched architecture, and studied its rare-earth-element chelation properties as a function of molecular weight (7−680 kDa) and degree of phosphonation (0−85%) using isothermal titration calorimetry (ITC). ITC enabled the determination of the full thermodynamic profile (ΔG, ΔH, ΔS, K a , and stoichiometry) for each polymer−REE interaction in aqueous solution. We observed entropically driven metal−polymer binding with five REEs, independent of polymer molecular weight and degree of functionalization. Finally, we characterized the metal-ion-induced aggregation behavior of these polymers using dynamic light scattering.

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Phosphonated Polyethyleneimines (PEIP) as Multi-Use Polymers

Cited by 12 publications

References 37 publications

Phosphonic acid: preparation and applications

Phosphonic acid: preparation and applications

2-Mercaptobenzimidazole derivative of chitosan for silver sorption – Contribution of magnetite incorporation and sonication effects on enhanced metal recovery

Synthesis and Rare-Earth-Element Chelation Properties of Linear Poly(ethylenimine methylenephosphonate)

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