New calix[4]arenedimethacrylate derivatives for dental composites

Tabatabai, Monir; Garska, Bernd; Fischer, Urs; Moszner, Norbert; Utterodt, Andreas; Ritter, Helmut

doi:10.1002/pi.3208

Cited by 6 publications

(4 citation statements)

References 24 publications

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“…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. 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.…”

Section: Restorative Compositessupporting

confidence: 61%

Patient‐reported outcome measures suitable to assessment of patient navigation

Fiscella

Ransom

Jean‐Pierre

et al. 2011

Cancer

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In the past 10 years, many new components were synthesized and evaluated for an application in enamel–dentin adhesives and direct composite restoratives. New bisacrylamide cross‐linkers with improved hydrolytic stability and new strongly acidic polymerizable phosphonic acids and dihydrogen phosphates, as well as novel photoinitator systems, in combination with the implementation of novel application devices, have significantly improved the performance of the current enamel–dentin adhesives. The currently used resins for direct composite restoratives are mainly based on methacrylate chemistry to this day. A continuous improvement of the properties of current composites was achieved with the use of new tailor‐made methacrylate cross‐linkers, new additives, and photoinitiators as well as tailor‐made fillers. Nowadays, dental adhesives and methacrylate‐based direct restorative materials have found wide‐spread acceptance. Nevertheless, future developments in the field of dental adhesives and direct composite restoratives will focus on improving durability and biocompatibility as well as the development of materials with a broader application spectrum and of smart adhesives or composites. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012

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Section: Restorative Compositessupporting

confidence: 61%

Patient‐reported outcome measures suitable to assessment of patient navigation

Fiscella

Ransom

Jean‐Pierre

et al. 2011

Cancer

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“…[ 1,[5][6][7][8][9] Two strategies are predominant in order to come up against the shrinkage stress: (i) the design of tailor made, bulky dimethacrylates and (ii) the use of alternative polymerization mechanisms such as polyaddition or ring-opening polymerization. [ 10 ] With respect to the fi rst approach tailor-made dimethacrylates with diverse backbone chemistry such as tricyclodecane, [ 11,12 ] bile acid, [ 13 ] calix [4]arene, [ 14,15 ] spirobisindane, [ 16 ] and others [17][18][19] have been synthesized and investigated. Regarding the alternative polymerization mechanism, the ring-opening polymerization of cyclopropane-derivatives, [ 20,21 ] epoxy-based siloranes, [ 22,23 ] as well as spiroorthocarbonates [23][24][25] has been investigated and led to improvements.…”

mentioning

confidence: 99%

Synthesis and Photopolymerization of Thiol‐Modified Triazine‐Based Monomers and Oligomers for the Use in Thiol‐Ene‐Based Dental Composites

Reinelt

Tabatabai

Moszner

et al. 2014

Macro Chemistry & Physics

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Thiol‐ene photopolymerizations combine the unique features of step‐growth reactions and photoinitiated polymerizations, so that they experience a growing interest for applications such as coatings or dental restoratives. Most studies have making use of a relatively flexible ester and the hydrolytically labile derivative pentaerythritoltetra(3‐mercaptopropionate) (PETMP) as the thiol component in common. In this study, the performance of hydrolytically stable 1,3,5‐tris(3‐mercaptopropyl)‐1,3,5‐triazine‐2,4,6‐trione (4a), 1,3,5‐tris(2‐methyl‐3‐mercapto‐propyl)‐1,3,5‐triazine‐2,4,6‐trione (4b), and oligomers thereof in thiol‐ene photopolymerizations is investigated. The oligomers are prepared via thiol‐Michael or thiol‐isocyanate additions by using 4a and suitable diacrylates or diisocyanates containing a rigid core structure. Compared with PETMP, the thiol derivative 4a shows better flexural strength and modulus of elasticity in thiol‐ene photopolymerizations with 1,3,5‐triallyl‐1,3,5‐triazine‐2,4,6‐trione (TATATO) as the‐ene derivative. This phenomenon becomes especially evident after storage in water at 37 °C for 24 h. Furthermore, the performance regarding the flexural strength, the Young's modulus of elasticity, the polymerization shrinkage stress of 4a, and the polyadducts thereof in dental filling composites is evaluated and discussed.

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“…Furthermore, we also observed the same effects for polymerizable calixarenes in composites based on calix [4]arene-dimethacrylate derivatives CA4DMA (Scheme 30: (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.…”

Section: Methacrylate Monomersmentioning

confidence: 99%

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

Moszner

Hirt

2012

J. Polym. Sci. A Polym. Chem.

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128

125

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In the past 10 years, many new components were synthesized and evaluated for an application in enamel-dentin adhesives and direct composite restoratives. New bisacrylamide cross-linkers with improved hydrolytic stability and new strongly acidic polymerizable phosphonic acids and dihydrogen phosphates, as well as novel photoinitator systems, in combination with the implementation of novel application devices, have significantly improved the performance of the current enamel-dentin adhesives. The currently used resins for direct composite restoratives are mainly based on methacrylate chemistry to this day. A continuous improvement of the properties of current composites was achieved with the use of new tailor-made methacrylate cross-linkers, new additives, and photoinitiators as well as tailor-made fillers. Nowadays, dental adhesives and methacrylate-based direct restorative materials have found wide-spread acceptance. Nevertheless, future developments in the field of dental adhesives and direct composite restoratives will focus on improving durability and biocompatibility as well as the development of materials with a broader application spectrum and of smart adhesives or composites. V C 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 50: 2012

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New calix[4]arenedimethacrylate derivatives for dental composites

Cited by 6 publications

References 24 publications

Patient‐reported outcome measures suitable to assessment of patient navigation

Patient‐reported outcome measures suitable to assessment of patient navigation

Synthesis and Photopolymerization of Thiol‐Modified Triazine‐Based Monomers and Oligomers for the Use in Thiol‐Ene‐Based Dental Composites

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

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