Novel 2-(ω-phosphonooxy-2-oxaalkyl)acrylate monomers for self-etching self-priming one part adhesive

• Joachim E. Klee and
• Uwe Lehmann

Beilstein J. Org. Chem. 2010, 6, 766–772, doi:10.3762/bjoc.6.95

• acrylate and formaldehyde, and subsequent etherification of the obtained product with diols and phosphorylation using POCl3. The polymerization enthalpy of 2-(ω-phosphonooxy-2-oxaalkyl)acrylates 3 as measured by DSC ranges from −29 to −53 kJ·mol−1. The shear bond strength of adhesive compositions 4

• , comprising of polymerizable acids 3, ranges from 5.8 to 19.3 MPa on enamel and from 8.7 to 16.9 MPa on dentin. Keywords: adhesion to enamel and dentin; hydrolysis stable 2-(ω-phosphonooxy-2-oxaalkyl)acrylates; phosphorylation using POCl3; polymerization enthalpy; shear bond strength; Introduction Dental

• bond conversion of 87.3% at 37 °C. Adhesion of phosphoric acids 3 The shear bond strength of adhesive compositions 4 [11], comprising of polymerizable acids 3, ranges from 5.8 to 19.3 MPa on enamel and from 8.7 to 16.9 MPa on dentin (Table 3, Figure 1). With increasing length of the aliphatic spacers

Synthesis of bis(3-{[2-(allyloxy)ethoxy]methyl}-2,4,6-trimethylbenzoyl)(phenyl)phosphine oxide – a tailor-made photoinitiator for dental adhesives

• Norbert Moszner,
• Iris Lamparth,
• Jörg Angermann,
• Urs Karl Fischer,
• Frank Zeuner,
• Thorsten Bock,
• Robert Liska and
• Volker Rheinberger

Beilstein J. Org. Chem. 2010, 6, No. 26, doi:10.3762/bjoc.6.26

• -dentin adhesive is mainly based on an aqueous mixture of the hydrolytically stable cross-linker DEBAMP and the strongly acidic adhesive monomer BMAMHP. For the investigation of the adhesive properties, the shear bond strength of corresponding compositions containing different PIs was measured as a

• Vivadent AG) and an irradiation time of 180 s at 37 °C. For the measurement of the shear bond strength of the corresponding dentin adhesives, freshly extracted bovine lower incisors were embedded in unsaturated polyester resin (Castolite, Buehler, USA) in cylindrical molds. Flat dentinal surfaces were

• specimens were immersed in water at 37 °C for 24 h prior to testing. Then the shear bond strength was measured using a universal testing machine (Zwick Z010, Germany) at a cross-head speed of 1.0 mm/min. 1H NMR spectra (400 MHz, CDCl3) of BAPO and WBAPO. UV–vis absorption spectra of WBAPO and CQ dissolved

N-alkyl-N-(phosphonoethyl) substituted (meth)acrylamides – new adhesive monomers for self-etching self-priming one part dental adhesive

• Joachim E. Klee and
• Uwe Lehmann

Beilstein J. Org. Chem. 2009, 5, No. 72, doi:10.3762/bjoc.5.72

• phosphonomethyl ester (4) after storage in aqueous solution at 50 °C. Etch pattern of enamel etched with a) Conditioner 36, magnification 11 × 103, b) acidic monomer 3g (c = 0.5 mol/l) in ethanol/water 1:1, magnification 11 × 103, c) Clearfil SE Primer, magnification 11 × 103. Shear bond strength (SBS) of