Homopolymerization and copolymerization of salt formed from a new diethyl styrenic phosphonate monomer

Boutevin, Bernard; Hamoui, Bachar; Parisi, Jean-Pierre; Améduri, Bruno

doi:10.1016/0014-3057(95)00132-8

Cited by 27 publications

(22 citation statements)

References 9 publications

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“…It was obtained after two steps in 42.9 gram scale and in an overall yield of 71%. The building block was prepared according to literature . First, the building block was converted with 4‐methoxybenzaldehyde or 4‐(dimethylamino)benzaldehyde in a HWE reaction.…”

Section: Liquid‐phase Synthesis Of Sequence‐defined Macromoleculesmentioning

confidence: 99%

Recent Progress in the Design of Monodisperse, Sequence-Defined Macromolecules

Solleder

Schneider

Wetzel

et al. 2017

Macromol. Rapid Commun.

181

173

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This review describes different synthetic strategies towards sequence-defined, monodisperse macromolecules, which are built up by iterative approaches and lead to linear non-natural polymer structures. The review is divided in three parts: solution phase-, solid phase-, and fluorous- and polymer-tethered approaches. Moreover, synthesis procedures leading to conjugated and non-conjugated macromolecules are considered and discussed in the respective sections. A major focus in the evaluation is the applicability of the different approaches in polymer chemistry. In this context, simple procedures for monomer and oligomer synthesis, overall yields, scalability, purity of the oligomers, and the achievable level of control (side-chains, backbone, stereochemistry) are important benchmarks.

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Section: Liquid‐phase Synthesis Of Sequence‐defined Macromoleculesmentioning

confidence: 99%

Recent Progress in the Design of Monodisperse, Sequence-Defined Macromolecules

Solleder

Schneider

Wetzel

et al. 2017

Macromol. Rapid Commun.

181

173

View full text Add to dashboard Cite

show abstract

“…However, the attempts in this direction described in the literature have mostly led to oligomeric products due to side-reactions. [8,9] Therefore, we have worked on the subsequent phosphonation of suitable commercial aromatic polymers. In the present article, we describe the first successful functionalization of polyarylsulfone with phosphonic acid pendant groups without using alkylene spacer units.…”

Section: Introductionmentioning

confidence: 99%

Palladium‐Catalyzed Phosphonation of Polyphenylsulfone

Jakoby

Peinemann

Nunes

2003

Macro Chemistry & Physics

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An efficient synthetic procedure for the phosphonation of aromatic polymers was developed and is here exemplified for polyphenylsulfone. This procedure involved the bromination of the polymer and the subsequent bromine‐phosphorus exchange by means of a Pd(0)‐catalyzed PC coupling reaction. In the resulting product, the phosphonate ester pendant groups were attached to aromatic rings of the polymer chain without alkylene spacer units. A substitution degree of almost one phosphonate moiety per repeating unit of the polymer was achieved in the presence of Pd2(dba)3 · CHCl3 as catalyst at 120 °C. Polymers with free phosphonic acid groups were prepared by ester hydrolysis. magnified image

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“…On the other hand, increasing the distance between the phosphonated group and the double bond leads to better reactivity of the double bond and decreases the steric effect. This can be achieved by introducing the phosphorus group in the para position of styrene type monomers, as reported by Boutevin27 and Garner 28. Thus, the aromatic ring served as a bulky and electron rich spacer between the double bond and the phosphorus groups.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of hydroxy‐bisphosphonate micrometer‐sized particles by dispersion polymerization of a new styrylbisphosphonate monomer

Chen

Goldshtein

Margel

2013

J. Polym. Sci. A Polym. Chem.

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Bisphosphonates (BPs) are nonhydrolyzable pyrophosphate (P‐O‐P) analogs possessing two phosphonate groups linked to a single carbon (P‐C‐P). The hydroxy‐bisphosphonates (hydroxyBPs) are obtained when the hydroxy group is also linked to this bridging carbon. Their ability to form bidentate or tridentate chelates with calcium ions results in a high affinity to hydroxyapatite (HAP) in dentin, enamel and bones. In this study, we designed and prepared crosslinked poly(styrylbisphosphonate) (PStBP) micrometer‐sized particles by dispersion polymerization of the styrylbisphosphonate (StBP) and ethylene glycol dimethacrylate (EDMA) monomers. The new StBP monomer was synthesized in an efficient one‐pot synthesis using tris(trimethylsilyl)phosphite as the phosphorus source followed by methanolysis. The StBP monomer was successfully isolated and characterized as tri‐sodium salt. Polymerization of the StBP monomer was carried out in two steps: in situ conversion of the tri‐sodium StBP monomer back to its acid form, followed by radical dispersion polymerization in the presence of the crosslinker EDMA monomer. The resulting crosslinked PStBP micrometer‐sized particles retained the unique high affinity of the hydroxy‐bisphosphonate side groups to calcium ions and exhibited good adhesive properties to HAP. © 2013 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013

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Homopolymerization and copolymerization of salt formed from a new diethyl styrenic phosphonate monomer

Cited by 27 publications

References 9 publications

Recent Progress in the Design of Monodisperse, Sequence-Defined Macromolecules

Recent Progress in the Design of Monodisperse, Sequence-Defined Macromolecules

Palladium‐Catalyzed Phosphonation of Polyphenylsulfone

Synthesis and characterization of hydroxy‐bisphosphonate micrometer‐sized particles by dispersion polymerization of a new styrylbisphosphonate monomer

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