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

• ) and in the 31P NMR spectra at 0.16 ppm (3h) and −0.11/0.07 ppm (3i). DSC Investigation of 3 The polymerization behavior of 2-(ω-phosphonooxy-2-oxaalkyl)acrylates 3 was investigated by photo-polymerization using a DSC 7/DPA 7 unit. The polymerization enthalpy of 2-(ω-phosphonooxy-2-oxaalkyl)acrylates 3

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

• substrates, namely 15.3 ± 3.4 MPa to enamel and 18.5 ± 2.3 MPa to dentin. Keywords: adhesion to enamel and dentin; hydrolytic stability; N-alkyl-N-(phosphonoethyl) substituted (meth)acrylamides; polymerization enthalpy; REM investigation; Introduction In the past decades dental adhesives have been employed

• polymerization enthalpy of acrylamides 3 (Table 2) is ranging from −50 to −70 kJ·mol−1 per double bond. It is only slightly lower compared to the polymerization enthalpy of acrylamide which was measured with −75.4 [10] and −82.9 kJ·mol−1 [11] and to acrylic esters (−77.5 to −80.5 kJ·mol−1 [12][13]). The longer

• the alkyl substituent and the higher the steric hindrance, the lower is the polymerization enthalpy of N-alkyl-N-(phosphonoethyl)acrylamides in the order of 3c, 3e and 3f. The diacrylamide 3g shows a relatively low polymerization enthalpy of −21.5 kJ·mol−1 per double bond when polymerized