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 phosphorylationusingPOCl3. 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; phosphorylationusingPOCl3; polymerization enthalpy; shear bond strength; Introduction
Dental
, comprising of phosphoric acid ester moieties, were synthesized via a three step synthesis via Baylis–Hillman reaction of ethyl acrylate and formaldehyde, and subsequent etherification of the obtained product with diols and phosphorylationusingPOCl3 (Scheme 1, Table 1).
The double bonds in 3 are evident in
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Graphical Abstract
Scheme 1:
Synthesis of novel ethyl 2-(ω-phosphonooxy-2-oxaalkyl)acrylates 3.