A review of the developments of multi-purpose primers and adhesives comprising novel dithiooctanoate monomers and phosphonic acid monomers

Abstract

This paper reviews the developments of dithiooctanoate monomers and acidic adhesive monomers, and their roles in multi-purpose primers and adhesives in promoting adhesion to multiple substrate materials. Novel dithiooctanoate monomers exhibited excellent bonding to precious metals and alloys when compared against conventional sulfur-containing monomers. Newly developed phosphonic acid monomers, endowed with a water-soluble nature, enabled sufficient demineralization of dental hard tissues and thus improved bonding to both ground enamel and dentin. The optimal combination for bonding to dental hard tissues and precious and non-precious metals and alloys was 5.0 wt% 10-methacryloyloxydecyl 6,8-dithiooctanoate (10-MDDT) and 1.0 wt% 6-methacryloyloxyhexyl phosphonoacetate (6-MHPA). For bonding to dental porcelain, alumina, zirconia, and gold (Au) alloy, a ternary combination of silane coupling agent, acidic adhesive monomers, and dithiooctanoate monomers seemed promising. The latest development was a singlebottle, multi-purpose, self-etching adhesive which contained only acidic adhesive monomers and dithiooctanoate monomers but which produced strong adhesion to ground enamel and dentin, sandblasted zirconia, and Au alloy.

Bonding Strength of Universal Adhesives to Indirect Substrates: A Meta‐Analysis of in Vitro Studies

“…Although it may affect the mechanical strength of some materials, an optimal bond could be achieved by roughening the intaglio surface of the restoration, a procedure that could be carried out by means of air abrasion, sandblasting, or etching with a hydrofluoric acid 7 . The application of a specific coupling agent on the pretreated surface improved the formation of chemical bonds between the components of the material and the cement 70,71 . Choosing between one or another mechanism, or a combination of both, depended on the chemical conformation and microstructure of each substrate 7 …”

Phosphonate‐Containing Polymeric Networks: Swelling in Water Controlled by Metal Ions

“…In medical and pharmaceutical applications, the phosphonates can regulate the calcium phosphate metabolism . They are used to combine organic materials like polymer‐based dental materials with the dentin surface strongly . In presence of suitable metal ions, the formation of soluble and insoluble complexes are possible …”

Monomers for Adhesive Polymers 12 Synthesis and Free‐Radical Homo‐ and Copolymerization of 2‐Ethoxycarbonylallyl 5‐(1,2‐dithiolane‐3‐yl)‐pentanoate

“…A number of polymerizable disulfides used as adhesive promoters for noble metal alloys are described in the patent literature and include, for example, bis(2‐methacryloyloxyethyl)disulfide, 2‐methacryloyloxyethyl 1,2‐dithiolane‐3‐pentanoate, and bis[( N ‐methacryloyl)‐cysteine ethyl ester]disulfide 9–11. Recently, a review described the development of dithiooctanoate monomers and acidic adhesive monomers and their roles in multi‐purpose primers and adhesives in promoting adhesion to multiple substrate materials 12…”