Multi-purpose Bonding Performance of Newly Synthesized Phosphonic Acid Monomers

Abstract

Multi-purpose bonding performance of three kinds of newly synthesized phosphonic acid monomers was investigated. Methacryloxyalkyl or acryloxyalkyl phosphonoacetates of 6-MHPA, 6-AHPA, 10-MDPA were synthesized in 42.8-51.9％ yields with a light yellow viscous liquid, and identified as new compounds by 1 H NMR, IR, and elemental analysis. Conventional adhesive monomers, namely VBPA, 4-META, and 4-AETA, and CEBA-p-TSMo-t-BPMA initiator were also used. Seven experimental composite-type adhesive resins comprising these six kinds of adhesive monomers and None (control) with the initiator were prepared. Tensile bond strengths of adhesive resins to unetched ground enamel and dentin, ground porcelain, and sandblasted Ni-Cr alloy were measured at a crosshead speed of 1.0 mm/min. Results showed that except with VBPA, there were no significant differences among 6-MHPA, 6-AHPA, 10-MDPA, 4-AETA, and 4-META in bonding performance to the adherends (p<0.01). It was found that the new phosphonic acid monomers provided good multipurpose adhesion to all adherends tested.

Is the Ditio-Octonoate Monomer the Ideal for Adhesion to Precious Metals and their Alloys?

“…It is at the end of the 70 when the first generation of adhesives appears; These monomers were 4-META (4-methacryloyloxyethyl trimellitate anhydride) and 10-MDP (10-methacryloyloxydecyl dihydrogen phosphate). These were effective for use with non-precious metal alloys [4]. At the end of the 80 appears the second generation of adhesives, which were effective with precious or noble metal alloys.…”

“…Examples of adhesion of enamel or dentin to metals, orthodontic bands and brackets, or Maryland type adhesive bridges. It may be necessary to attach a metal to ceramics in the case of a metal crown, which by aesthetics will be covered or another metal (such as a cast post) to the metal of the crown and / or ceramics thereof, or even when it is free of metal [4].…”

“…Examples of adhesion of enamel or dentin to metals, orthodontic bands and brackets, or Maryland type adhesive bridges. It may be necessary to attach a metal to ceramics in the case of a metal crown, which by aesthetics will be covered or another metal (such as a cast post) to the metal of the crown and / or ceramics thereof, or even when it is free of metal [4].The first and foremost objective of dental adhesives is the long-lasting attachment to their substrates or adhesives, whether hard dental tissues or a wide range of materials (some new and others already contaminated when already in the mouth). The adhesive system, already discovered by Bouncoure and Bowen in the 1960s, has meant an improvement in speed, efficiency and convenience by simplifying the joining steps of two bodies of disparate origin and nature and reducing the time in the clinician's working time.…”

Design of a metal primer containing a dithiooctanoate monomer and a phosphonic acid monomer for bonding of prosthetic light-curing resin composite to gold, dental precious and non-precious metal alloys

“…In the course of our development of a multi-purpose adhesive, several acidic adhesive monomers bearing carboxylic acid (-COOH) or its anhydride group 26) and phosphonic acid group 19,27) were previously developed. Besides, eight kinds of acryloyloxyalkyl and methacryloyloxyalkyl 6,8-dithiooctanoates (dithiooctanoate monomers) as novel sulfur-containing monomers were also developed 28) .…”

“…For phosphonic acid monomers ( Fig. 1(b)) -namely, 6-MHPA and 6-MHPP, they were synthesized via an esterification reaction between 6-hydroxyhexyl methacrylate and phosphonoacetic acid or 2-carboxyethylphosphonic acid as previously described 19,27) .…”