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

Abstract

SummaryNovel 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 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.

Synthesis and Properties of Novel Surface Active Monomers Based on Derivatives of 4‐Hydroxybutyric Acid and 6‐Hydroxyhexanoic Acid

“…As it can be concluded, the introduction of hydrophilic groups of various natures and hydrophobic chains of different lengths gives an opportunity to vary the surface active properties of the synthesized surfmers over a wide range. It is worth mentioning that values of CMC reported in the literature for various types of surfmers vary over a wide range [27,28,33,34,40,42]. Such values are significant for an insight into the interfacial behavior of amphiphiles according to previously published papers.…”

“…Variation of nature of polymerizable unit impacts on the polymerization capability of surfmers and on the microstructure of the copolymer backbone respectively. Nowadays, a wide range of maleate [33][34][35][36][37], (meth)acrylate [38][39][40][41][42] and styrene [43][44][45][46] surfmers have been synthesized.…”

New polymer‐chemical developments in clinical dental polymer materials: Enamel–dentin adhesives and restorative composites

“…28,33,34 Furthermore, novel 2-(x-phosphonooxy-2oxaalkyl)acrylate monomers (POAA; Scheme 10) with improved hydrolytic stability were synthesized by a four-step synthesis involving a Baylis-Hillmann reaction between ethyl acrylate and formaldehyde, followed by halogenation, a subsequent etherification with various diols and a phosphorylation. 35 Compared to the (meth)acrylamido dihydrogen phosphates, however, these monomers are still less hydrolytically stable because of the presence of terminal ester groups.…”

Patient‐reported outcome measures suitable to assessment of patient navigation

“…Thus, a new hydrolytically stable one‐component SEA, which can be stored at room temperature, was successfully developed using BMAPDP, the cross‐linker DEBAAP (Scheme ), and the hydrolytically stable N ‐(5‐hydroxypentyl)methacrylamide as alternative to HEMA 28,33,34. Furthermore, novel 2‐(ω‐phosphonooxy‐2‐oxaalkyl)acrylate monomers (POAA; Scheme ) with improved hydrolytic stability were synthesized by a four‐step synthesis involving a Baylis–Hillmann reaction between ethyl acrylate and formaldehyde, followed by halogenation, a subsequent etherification with various diols and a phosphorylation 35. Compared to the (meth)acrylamido dihydrogen phosphates, however, these monomers are still less hydrolytically stable because of the presence of terminal ester groups.…”