Methacrylated Calix[6]arenes as Low Shrinking Additives for Dental Restorative Composites

Abstract

p‐tert‐Butylcalix[6]arene was acylated with different carboxylic acid anhydrides to improve their solubility in dimethacrylate cross‐linkers. An esterification of p‐tert‐butylcalix[6]arene 1 with octanoic anhydride followed by methacrylation of the residual hydroxy groups with methacrylic anhydride resulted mainly in the formation of a pentaoctanoatemonomethacrylate 2a. In the radical polymerization of methyl methacrylate the inhibition effect of residual hydroxy groups in 2a was evaluated. Dimethacrylate containing composites based on a monomer matrix of cross‐linking dimethacrylates and 0–30 wt.% of 2a were prepared. The addition of 2a resulted in a significant decrease of the polymerization shrinkage, whereas the modulus of elasticity of the visible light cured composites was not affected.

New calix[4]arenedimethacrylate derivatives for dental composites

“…Calixarenes are cyclic oligomers of para ‐ tert ‐butylphenol and formaldehyde 8, 9. Calixarenemethacrylates are known in polymer chemistry,10 and some of them have been employed and patent‐registered in dental materials11–13 leading to a lower polymerization shrinkage in comparison to conventional linear dimethacrylates 14–18. However, the solubility of simple calixarenemethacrylates in monomer matrices is a problem.…”

Calix[4]arene‐tetranitrone as crosslinker in dental composite materials

“…Surprisingly, up to now, there have been only two publications dealing with the synthesis and applications of calixarenes bearing 1,3‐dipolar nitrones 17, 18. Thus, in the present paper, we present our results dealing with the synthesis and modification via cyclo‐addition of new calix[4]arene derivatives bearing four nitrone functions in the ‘upper rim’.…”

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

“…Accordingly, an acid-catalyzed esterification of p-tert-butylcalix [6]arene with octanoic anhydride followed by the methacrylation of the residual hydroxy groups with methacrylic anhydride (Scheme 30: (a)) mainly resulted in the formation of a pentaoctanoatemonomethacrylate CAOMA, which showed a significantly improved solubility, for example, in TEGDMA. 140,141 Dimethacrylate-containing composites with a filler load of 60 or 85 wt % based on a monomer matrix of cross-linking dimethacrylates and 0-30 wt % CAOMA were prepared. The addition of CAOMA to the dental composite formulations resulted in a significant decrease of the polymerization shrinkage, whereas the modulus of elasticity of the visible light-cured composites was not affected.…”