Synthesis and evaluation of new phosphonic, bisphosphonic and difluoromethylphosphonic acid monomers for dental application

Yohann Catel (1) , Vincent Besse , Anaïs Zulauf (1) , David Marchat (2) , Emmanuel Pfund (1) , Thi-Nhàn Pham (1) , Didier Bernache-Assollant (2) , Michel Degrange (3) , Thierry Lequeux (1) , Pierre-Jean Madec (1) , Loïc Le Pluart (1)

1 LCMT - Laboratoire de chimie moléculaire et thioorganique
2 CIS-ENSMSE - Centre Ingénierie et Santé
3 URB2i - EA 4462 - Unité de Recherche Biomatériaux Innovants et Interfaces

Syntheses of novel 5-(methacryloyloxy)pentylphosphonic acid 1, 5-(methacryloyloxy)pentylidenebisphosphonic acid 2 and 1,1-difluoro-5-(methacryloyloxy)pentylphosphonic acid 3 are described. The ability of these monomers to adhere to hydroxyapatite was demonstrated using 31P CP-MAS NMR spectroscopy. Their copolymerization with N,N′-diethyl-1,3-bis(acrylamido)propane (DEBAAP) was investigated with photo differential scanning calorimetry. These mixtures exhibit a significantly higher reactivity than DEBAAP alone. Bisphosphonic acid 2 was shown to be significantly more reactive than monomers 1 and 3. Adhesive properties of these monomers were also studied. Adhesives based on bisphosphonic acid 2 and difluoromethylphosphonic acid 3 provide significantly higher dentin shear bond strength than the one based on phosphonic acid 1.

Mots clés: Dental adhesives; Synthesis; Hydroxyapatite; Photopolymerization; Adhesion

Domaines: Polymères

Yohann Catel, Vincent Besse, Anaïs Zulauf, David Marchat, Emmanuel Pfund, et al.. Synthesis and evaluation of new phosphonic, bisphosphonic and difluoromethylphosphonic acid monomers for dental application. European Polymer Journal, 2012, 48 (2), pp.318. ⟨10.1016/j.eurpolymj.2011.09.020⟩. ⟨hal-00839843⟩