Ring‐opening bulk polymerization of five‐ and six‐membered cyclic phosphonates using maghnite, a nontoxic proton exchanged montmorillonite clay

Karima, Oussadi; Montembault, Véronique; Belbachir, Mohammed; Fontaine, Laurent

doi:10.1002/app.34193

Cited by 15 publications

(9 citation statements)

References 59 publications

(70 reference statements)

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“…In some cases, the synthesis of cyclic phosphates is based on reverse reaction sequence, i.e., substitution of Cl in chlorophosphite followed by oxidation ( Scheme 9 c) [ 62 ]. Cyclic phosphonates can also be synthesized by the reaction of diols with dialkyl phosphonates [ 63 , 64 ] ( Scheme 9 d).…”

Section: Design and Synthesis Of Polyphosphodiestersmentioning

confidence: 99%

Design, Synthesis and Actual Applications of the Polymers Containing Acidic P–OH Fragments: Part 1. Polyphosphodiesters

Nifant’ev

Ivchenko

2022

IJMS

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Among natural and synthetic polymers, main-chain phosphorus-containing polyacids (PCPAs) (polyphosphodiesters), stand in a unique position at the intersection of chemistry, physics, biology and medicine. The structural similarity of polyphosphodiesters PCPAs to natural nucleic and teichoic acids, their biocompatibility, mimicking to biomolecules providing the ‘stealth effect’, high bone mineral affinity of polyphosphodiesters resulting in biomineralization at physiological conditions, and adjustable hydrolytic stability of polyphosphodiesters are the basis for various biomedical, industrial and household applications of this type of polymers. In the present review, we discuss the synthesis, properties and actual applications of polyphosphodiesters.

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Section: Design and Synthesis Of Polyphosphodiestersmentioning

confidence: 99%

Design, Synthesis and Actual Applications of the Polymers Containing Acidic P–OH Fragments: Part 1. Polyphosphodiesters

Nifant’ev

Ivchenko

2022

IJMS

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“…It necessitated the implementation of a stepwise protocol, via the corresponding allyl phosphonate ester 6. The latter was successfully derived from either the cyclic dialkylphosphite 4 25,26 or the trialkylphosphite 5, then epoxidized to the target structure 1b using MCPBA. Originally, we conducted the epoxidation process at ambient temperature, in THF, following the procedure of Perie et al 18 However, the product mixtures contained large amounts of unreacted starting material.…”

Section: Synthesismentioning

confidence: 99%

Synthesis and flammability testing of epoxy functionalized phosphorous‐based flame retardants

Benin

Cui

Morgan

et al. 2015

J of Applied Polymer Sci

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Several potential new phosphorus-containing flame retardant molecules were evaluated for heat release reduction potential by incorporation of the molecules into a polyurethane, generated from methylene diphenyl diisocyanate and 1,3-propane diol. The heat release reduction potential of these substances was evaluated using the pyrolysis combustion flow calorimeter (PCFC). The polyurethanes were prepared in the presence of the potential flame retardants via solvent mixing and copolymerization methods to qualitatively evaluate their potential reactivity into the polyurethane prior to heat release testing. The functionality of the flame retardants was epoxide based that would potentially react with the diol during polyurethane synthesis. Flammability testing via PCFC showed that the heat release reduction potential of each of the flame retardants was structure dependent, with phosphates tending to show more effectiveness than phosphonates in this study, and alkyl functionalized phosphorus groups (phosphate or phosphonate) being more effective at heat release reduction than cyclic functionalized groups.

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“…Polycondensation as a process for the preparation of amphiphilic polyphosphoesters has significant advantages compared to the polymerization process, namely (i) different starting hydroxyl-containing compounds can be used; (ii) synthesis can proceed without a catalyst; (iii) there is no need for the purification of the reaction product; (iv) degraded products can be designed in advance; (v) copolymers can be obtained; and (vi) there are commercially available starting monomers. Poly(alkylene H-phosphonate)s offers a unique opportunity to introduce various modifications at the phosphorus center through different reaction schemes [2][3][4][5][6][7][8][9][10][11]. Poly(oxyethylene H-phosphonate)s are multifunctional drug carriers, capable of converting into (i) hydrophilic; (ii) hydrophobic; (iii) amphiphilic, micelles, and (iv) stimuli-responsive poly(alkyloxyethylene phosphate)s. The drug can be carried (v) chemically (covalent bond), due to the presence of a highly reactive P-H group [12]; (vi) via ionic bonds (P-OH group) [12,13]; (vii) physically, due to the presence of a strong proton acceptor-P=O group [14], and via micelles [15,16].…”

Section: Introductionmentioning

confidence: 99%

pH-Sensitive Amphiphilic Diblock Polyphosphoesters with Lactate Units: Synthesis and Application as Drug Carriers

Mochizuki,

Mitova,

Makino

et al. 2024

IJMS

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pH-sensitive amphiphilic diblock polyphosphoesters containing lactic acid units were synthesized by multistep one-pot polycondensation reactions. They comprise acid-labile P(O)-O-C and C(O)-O-C bonds, the cleavage of which depends on the pH of the medium. The structure of these copolymers was characterized by 1H, 13C {H}, 31P NMR, and size exclusion chromatography (SEC). The newly synthesized polymers self-assembled into the micellar structure in an aqueous solution. The effects of the molecular weight of the copolymer and the length of the hydrophobic chain on micelle formation and stabilityand micelle size were studied via dynamic light scattering (DLS). Drug loading and encapsulation efficiency tests using doxorubicin revealed that hydrophobic drugs can be delivered by copolymers. It was established that the molecular weight of the copolymer, length of the hydrophobic chain and content of lactate units affects the size of the micelles, drug loading, and efficiency of encapsulation. A copolymer with 10.7% lactate content has drug loading (3.2 ± 0.3) and efficiency of encapsulation (57.4 ± 3.2), compared to the same copolymer with 41.8% lactate content (1.63%) and (45.8%), respectively. It was demonstrated that the poly[alkylpoly(ethylene glycol) phosphate-b-alkylpoly(ethylene glycol)lactate phosphate] DOX system has a pH-sensitive response capability in the result in which DOX was selectively accumulated into the tumor, where pH is acidic. The results obtained indicate that amphiphilic diblock polyphosphoesters have potential as drug carriers.

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Ring‐opening bulk polymerization of five‐ and six‐membered cyclic phosphonates using maghnite, a nontoxic proton exchanged montmorillonite clay

Abstract: International audienc

Cited by 15 publications

References 59 publications

Design, Synthesis and Actual Applications of the Polymers Containing Acidic P–OH Fragments: Part 1. Polyphosphodiesters

Design, Synthesis and Actual Applications of the Polymers Containing Acidic P–OH Fragments: Part 1. Polyphosphodiesters

Synthesis and flammability testing of epoxy functionalized phosphorous‐based flame retardants

pH-Sensitive Amphiphilic Diblock Polyphosphoesters with Lactate Units: Synthesis and Application as Drug Carriers

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