Dentsply De Trey, De-Trey-Str. 1, 78467 Konstanz, Germany.
Beilstein J Org Chem. 2010 Sep 7;6:766-72. doi: 10.3762/bjoc.6.95.
Novel hydrolysis stable 2-(ω-phosphonooxy-2-oxaalkyl)acrylate monomers 3 with phosphoric acid moieties were synthesized by a three step synthesis via Baylis-Hillman reaction of ethyl acrylate and formaldehyde, and subsequent etherification of the obtained product with diols and phosphorylation using POCl(3). 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.
新型水解稳定的 2-（ω-膦酸氧基-2-氧代烷基）丙烯酸酯单体 3 具有磷酸部分，通过 Baylis-Hillman 反应由丙烯酸乙酯和甲醛合成，然后通过与二醇的醚化和使用 POCl(3)的磷酸化得到产物。通过 DSC 测量，2-（ω-膦酸氧基-2-氧代烷基）丙烯酸酯 3 的聚合焓值范围为-29 至-53 kJ·mol(-1)。包含可聚合酸 3 的粘合剂组合物 4 的剪切结合强度在牙釉质上为 5.8 至 19.3 MPa，在牙本质上为 8.7 至 16.9 MPa。
