Synthesis of poly(oxyethylene phosphonate)s bearing oxirane groups in the side chain

Tzevi, R.; Novakov, P.; Troev, K.; Roundhill, D. Max

doi:10.1002/(sici)1099-0518(199703)35:4<625::aid-pola4>3.0.co;2-o

Cited by 18 publications

(8 citation statements)

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“…The following four important methods for the polymeric phosphonate esters preparation have been used during past decades: – polycondensation, – polyaddition, – the ROP of cyclic phosphonate monomers, and – transesterification …”

Section: Discussionmentioning

confidence: 99%

“…A typical reaction of the P–H group is the addition reaction to unsaturated carbonyl group C=O (Abramov reaction), to C=C (Pudovik reaction), or to the more unsaturated C≡C, resulting into P–C bond formation . The addition of the P–H groups of poly(oxyethylene H‐phosphonate)s to 1,2‐epoxy‐7‐octene in the presence of the catalyst benzoylperoxide leads to a poly(oxyethylene phosphonate)s bearing oxirane cycle in the side chain . If in the same precursor polymers react with chloroacetone under phase‐transfer catalysis conditions, the addition reaction will produce polymers bearing hydroxyl and oxirane groups …”

Section: Methods To Obtain Ppesmentioning

confidence: 99%

“…One of the possibility to avoid this is to convert the highly reactive P-H bond to P-C or P-O bonds, for example. 44 If in the same precursor polymers react with chloroacetone under phase-transfer catalysis conditions, the addition reaction will produce polymers bearing hydroxyl and oxirane groups. 9,26,[32][33][34] The synthesis of reactive polymers is one of the most challenging, interesting, and important areas in the research of polymer science.…”

Section: Transesterificationmentioning

confidence: 99%

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The Use of Transesterification Method for Obtaining Phosphorus‐Containing Polymers

et al. 2014

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An introduction and overview of the transesterification method is presented in this review. This method is a very convenient way to obtain polyphosphoesters (PPEs). It can be simply described as a chemical reaction in which an ester is transformed into another one by the exchange of alkoxy groups. In this review, we will refer to the synthesis of PPEs via transesterification. In other words, it is focused on the applications of the transesterification method in phosphorus chemistry to obtain polymers (PPEs). The PPEs are an interesting class of organophosphorus polymers. These compounds are important for biological applications because of their biocompatibility and similarity to biopolymers. When the products are polymers, the chemical reaction is called polytransesterification. This method has also several applications in industry (esters of oil, paint industry). C

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Section: Discussionmentioning

confidence: 99%

Section: Methods To Obtain Ppesmentioning

confidence: 99%

Section: Transesterificationmentioning

confidence: 99%

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The Use of Transesterification Method for Obtaining Phosphorus‐Containing Polymers

et al. 2014

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“…Phosphonylation decreased the crystallinity of polyethylene as well as increased water sorption. Pretula et al and later on Bezdushna et al have introduced dimethyl hydrogen phosphonate into a polyethylene glycol chain by trans‐esterification 4–7. For the latter team, the random copolymers exhibiting POCH 3 functions on both ends were hydrolyzed into phosphonic acid groups, whereas hydrogen phosphonate PH inner groups could be derived into oxirane groups by radical or phase transfer catalysis.…”

Section: Introductionmentioning

confidence: 99%

Phosphonic acid functionalized polyethylene glycol and derivatives

Essahli¹,

Ganachaud²,

Martin³

et al. 2008

J of Applied Polymer Sci

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This article describes the functionalization of polyethylene glycol, mono or bifunctional, and a nonionic surfactant by phosphonic acids without the need for protection of the functional group. The functionalization is performed in two steps, first an esterification by thioglycolic acid, secondly a radical addition of vinyl phosphonic acid on the thiol group. All products were obtained quantitatively and characterized by 1 H-, 13 C-, 31 P-NMR spectroscopy techniques, MALDI, and step-by-step chemical titrations. Enhanced thermal properties were found while phosphonylating polyethylene glycol, particularly when the sulfur atom was oxidized into a sulfone group.

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“…The other major disadvantage is the low drug-loading capacity of this polymer, limited by the availability of only two attachment sites at the termini of the linear PEG molecule. Promising candidates for an immobilization template are the poly(oxyalkylene phosphates), POAP, a family of biodegradable, hydrophilic, and nontoxic polymers that contain PEG moieties and suitable multifunctional sites for immobilization …”

Section: Introductionmentioning

confidence: 99%

Immobilization of Aminothiols on Poly(oxyalkylene phosphates). Formation of Poly(oxyethylene phosphates)/Cysteamine Complexes and Their Radioprotective Efficiency

Georgieva

Tsevi²,

Titorenkova³

et al. 2002

J. Med. Chem.

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The necessity to apply near-toxic amounts of radioprotective drugs to achieve adequate protection during radiation treatments represents a major problem in human medicine. One of the promising strategies to suppress the toxicity of these drugs involves their incorporation into biocompatible polymers. In this study cysteamine (Cy) was attached to poly(oxyethylene phosphate), POEP, via an ionic bond. Radioprotection of E. coli B cells by this substance and its acute toxicity on male C57 BL mice were measured. The toxicity of Cy immobilized within the poly(oxyethylene phosphate) was significantly lower in comparison to pure Cy while its radioprotective efficiency remained high at half the maximum tolerable dose. The high radioprotective efficiency of the Cy/POEP complexes was further confirmed on mice at different polymer molecular weight characteristics, drug immobilization degrees, application times, and doses. It was found that POEP with molecular weight 4700 Da and containing 24% repeating units with attached Cy has the highest protection potential combined with a depot effect.

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Synthesis of poly(oxyethylene phosphonate)s bearing oxirane groups in the side chain

Cited by 18 publications

References 0 publications

The Use of Transesterification Method for Obtaining Phosphorus‐Containing Polymers

The Use of Transesterification Method for Obtaining Phosphorus‐Containing Polymers

Phosphonic acid functionalized polyethylene glycol and derivatives

Immobilization of Aminothiols on Poly(oxyalkylene phosphates). Formation of Poly(oxyethylene phosphates)/Cysteamine Complexes and Their Radioprotective Efficiency

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