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

Abstract

The synthesis of a functionalized calix[4]arene bearing 1,3-dipolaric nitrone groups (5) has been carried out. The reaction of N-methylhydroxylamine or N-propylhydroxylamine with the carbonyl group of 5,11,7,23-tetraformyl-25,26,27,28tetraalkoxycalix[4]arene leads to calix[4]arenes bearing a nitrone function at each of the four para-positions. Via 1,3-dipolar cyclo-addition of acrylic acid methyl ester with the nitrone functions of 5, subsequently an upper rim-substituted tetraisoxalidinecalix[4]arene is quantitatively synthesized. Further, the minimization of shrinkage of a dental filling depending on the amount of calix[4]arene-tetranitrone is discussed.

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.…”

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

“…142 A functionalized calix [4]arene CA4N bearing 1,3-dipolaric nitrone groups was prepared by the reaction of N-methylhydroxylamine with the carbonyl groups of 5,11,17,23-tetraformyl-25,26,27,28-tetrabutoxycalix [4]arene. 143 The nitrone groups may undergo a 1,3-dipolar addition reaction with (meth)acrylic double bonds. Thus, calixarene nitrones were able to react with typical dental dimethacrylates under formation of new multifunctional cross-linkers of higher molecular weight.…”

Patient‐reported outcome measures suitable to assessment of patient navigation

“…Furthermore, we also observed the same effects for polymerizable calixarenes in composites based on calix[4]arene‐dimethacrylate derivatives CA4DMA (Scheme : (b)), which we synthesized by dialkylation of p‐ tert‐ butyl‐calix[4]arene followed by diacylation with methacryloyl chloride 142. A functionalized calix[4]arene CA4N bearing 1,3‐dipolaric nitrone groups was prepared by the reaction of N ‐methylhydroxylamine with the carbonyl groups of 5,11,17,23‐tetraformyl‐25,26,27,28‐tetrabutoxycalix[4]arene 143. The nitrone groups may undergo a 1,3‐dipolar addition reaction with (meth)acrylic double bonds.…”