Fluorophosphonylated Monomers for Dental Applications

Abstract

International audienceThe synthesis of acrylate derivatives bearing a difluorophosphonic acid function has been realized by ring-opening reaction of oxacycles and alkylation of fluorinated carbanions. Their use in self-etch adhesives is reported. The resulting adhesives based on difluorophosphonic acid monomers provide significantly higher dentin shear bond strength (SBS) than the one based on phosphonic acid, mainly due to the presence of fluorine atoms

A straightforward synthesis of well‐defined difluorophosphonylated terminated poly(ε‐caprolactone) for grafting onto iron oxide magnetic nanoparticles

“…1,4 However, the low pKa 2 value of phosphonic acid and the hydrolyzable phosphate or phosphoric acid could limit their use for medicinal applications. 5 To address these issues, the difluoromethylphosphonate (or difluorophosphonate, pCF 2 ) derivatives and difluorophosphonic acid have been considered as interesting candidates for pharmaceutical and biomaterials applications [5][6][7][8][9] due to their resistance toward enzyme degradation and water hydrolysis. 6,[10][11][12] Additionally, difluorophosphonic acid is a stronger acid than phosphonic or phosphoric acids.…”

“…10 As long-standing interest in our laboratory, we were pioneers in the development of pCF 2 -functionalized monomers and polymers as potent self etching primers for dental applications. 5,9 Recently, we reported well-defined pCF 2 -functionalized polymers synthesized by reversible additionfragmentation chain transfer polymerization, in which the pCF 2 group was not only introduced into the polymer backbone but also at the macromolecular chain-ends. 13 Most polymers bearing pCF 2 groups are based on poly(meth)acrylic backbones which are not degradable at physiological pH (7.4).…”

“…Moreover, block copolymer based on PCL bearing phosphorous groups have been synthesized. 24 Beside the interest of pCF 2 function in term of stability, 5,6,[10][11][12][13] to the best of our knowledge, no previous studies have been reported on the synthesis of pCF 2 -functionalized PCL.…”

Synthesis and characterization of innovative well-defined difluorophosphonylated-(co)polymers by RAFT polymerization

“…They would be capable of forming stronger bindings with calcium ions, the main inorganic component of the dental hard tissue hydroxyapatite (HAp) and oxide surfaces than phosphate group. 27 Thanks to their good adhesive and biocompatible properties, we have successfully demonstrated that pCF 2 -functionalized (meth)acrylate monomers can be used as etching adhesive-primer for dental applications. [27][28][29] Besides, polymers bearing difluorophosphonic groups show a high proton conductivity for replacing perfluorosulfonic acid based polymer such as Nafion.…”

“…27 Thanks to their good adhesive and biocompatible properties, we have successfully demonstrated that pCF 2 -functionalized (meth)acrylate monomers can be used as etching adhesive-primer for dental applications. [27][28][29] Besides, polymers bearing difluorophosphonic groups show a high proton conductivity for replacing perfluorosulfonic acid based polymer such as Nafion. 30,31 However, up to now, only a few examples of pCF 2 group introduction in materials science were reported in the literature.…”