Monomers for adhesive polymers, 18. Synthesis, photopolymerization and adhesive properties of polymerizable α-phosphonooxy phosphonic acids

Abstract

Four polymerizable α-phosphonooxy phosphonic acids 7a, 7b, 9 and 16 were synthesized in seven steps. They were characterized by 1H, 13C and 31P NMR spectroscopy and by high-resolution mass spectroscopy. The copolymerization of acidic monomers 7a, 7b, 9 and 16 with 2-hydroxyethyl methacrylate was studied using a differential scanning calorimeter. Due to the presence of two acidic groups, those monomers are significantly more reactive than 10-methacryloyloxydecylphosphonic acid (MDPA) and 10-methacryloyloxydecyl dihydrogen phosphate (MDP). Self-etch adhesives based on monomers 7a, 7b, 9 and 16 were formulated and used to mediate a bond between a dental composite and the dental hard tissues (dentin and enamel). These adhesives exhibit excellent performances and provide significantly higher dentin and enamel shear bond strength than adhesives based on MDP or MDPA.

Enhanced reduction of polymerization-induced shrinkage stress via combination of radical ring opening and addition fragmentation chain transfer

“…VCP or EVS). Therefore, calculating the double bond conversion (DBC) via the recorded heat of polymerization can only be achieved with the pure MA (65%, 54.8 kJ mol −1 for a monofunctional MA giving a theoretical heat for the MA mixture of 263.9 J g −1 ) 33 and VCP resins (58%, 98 kJ mol −1 for a monofunctional VCP giving a theoretical heat for the VCP mixture of 401.5 J g −1 ). 34 However, as stated in the photoreactor studies of the monofunctional VCP/EVS system a good coreactivity of EVS with crosslinking VCPs can be assumed.…”

Synthesis and photopolymerizations of first monomers with phosphonate and bisphosphonate or phosphonic and bisphosphonic acid functionalities for potential dental applications

“…In dentistry, composites and self‐etching adhesive resin formulations contain about 15 wt % of adhesive monomers, and similar formulations are investigated in the literature . Therefore, we also investigated copolymerizations of HEMA:M1 (90:10 and 80:20 mol %) and HEMA:M2 (90:10 and 70:30 mol %) mixtures (Figs.…”

Combination of nuclear magnetic resonance spectroscopy and nonlinear methods to analyze the copolymerization of phosphonic acid derivatives

“…Acrylates and methacrylates with phosphonic acid‐containing substituents are important monomers for dental applications, for instance as enamel/dentin adhesives . Adhesive formulations normally contain several comonomers as mixture.…”

“…Acrylates and methacrylates with phosphonic acid-containing substituents are important monomers for dental applications, for instance as enamel/dentin adhesives. [1][2][3][4] Adhesive formulations normally contain several comonomers as mixture. Often used are 2-hydroxyethyl methacrylate (HEMA), an acidic monomer as key component for etching, for example, (2-{[2-(ethoxycarbonyl)prop-2-en-1-yl]oxy} ethyl) phosphonic acid (ECPPA), and crosslinkers, for instance 2,2-bis[4-(2-hydroxy-3-methacryloyl-oxypropoxy)phenyl]propane.…”