Online citations, reference lists, and bibliographies.
← Back to Search

Synthesis And Polymerization Of Vinylcyclopropanes Bearing Urethane Groups For The Development Of Low-shrinkage Composites

Yohann Catel, Pascal Fässler, Urs Karl Fischer, Christian Gorsche, R. Liska, Sebastian Schörpf, Sven Tauscher, N. Moszner
Published 2018 · Materials Science

Cite This
Download PDF
Analyze on Scholarcy
Abstract Polymerization shrinkage of methacrylate-based dental composites remains a major concern in restorative dentistry. Cyclic monomers, such as 1,1-disubstituted 2-vinylcyclopropanes, might represent an interesting alternative to dimethacrylates in order to reduce shrinkage. In this contribution, the synthesis of seven crosslinking vinylcyclopropanes bearing urethane groups is described. These monomers were synthesized by esterification of 1-ethoxycarbonyl-2-vinylcyclopropane-1-carboxylic acid with either ethylene glycol or diethylene glycol, followed by a reaction with selected diisocyanates. In order to evaluate the reactivity of the synthesized vinylcyclopropanes, their photopolymerization behavior was investigated by photo-differential scanning calorimetry. Real-time (RT)-NIR-photorheology measurements were performed to evaluate rheological behavior (i.e. time of gelation, polymerization induced shrinkage force) and chemical conversion (i.e. double bond conversion at the gel point, final double bond conversion) of the vinylcyclopropanes in situ. Composites based on these monomers show good to excellent mechanical properties and exhibit low shrinkage. The presence of urethane groups provides a significant improvement of the mechanical properties. The replacement of methacrylates by urethane vinylcyclopropanes appears to be a promising approach to develop low-shrinkage dental composites without sacrificing the mechanical properties.
This paper references
Synthesis and characterization of a dimethacrylates monomer with low shrinkage and water sorption for dental application
J. He (2012)
Polymerization of cyclic monomers. VII. Synthesis and radical polymerization of 1,3-bis[(1-alkoxycarbonyl-2-vinylcyclopropane-1-yl)carboxy]benzenes
N. Moszner (1999)
The influence of vinyl activating groups on β‐allyl sulfone‐based chain transfer agents for tough methacrylate networks
Paul Gauss (2016)
Synthesis and polymerization of vinylcyclopropanes
N. Moszner (1999)
Resin composite--state of the art.
J. Ferracane (2011)
Siloranes in dental composites.
W. Weinmann (2005)
Real Time-NIR/MIR-Photorheology: A Versatile Tool for the in Situ Characterization of Photopolymerization Reactions.
Christian Gorsche (2017)
Benzoylgermanium Derivatives as Novel Visible‐Light Photoinitiators for Dental Composites
N. Moszner (2009)
Bis(4‐methoxybenzoyl)diethylgermane: A Highly Efficient Photoinitiator for the Polymerization of Vinylcyclopropanes
Yohann Catel (2016)
Role of filler and functional group conversion in the evolution of properties in polymeric dental restoratives.
P. K. Shah (2014)
Synthesis and Photopolymerization of Thiol-Modified Triazine-Based Monomers and Oligomers for the Use in Thiol-Ene-Based Dental Composites
Sebastian Reinelt (2014)
Polymerization shrinkage, stress, and degree of conversion in silorane- and dimethacrylate-based dental composites
J. Xiong (2011)
Renaissance for low shrinking resins: all-in-one solution by bi-functional vinylcyclopropane-amides.
Paul Pineda Contreras (2015)
Ester-free thiol-ene dental restoratives--Part B: Composite development.
M. Podgórski (2015)
Synthesis of glycerol-derived diallyl spiroorthocarbonates and the study of their antishrinking properties in acrylic dental resins.
R. Ortiz (2013)
New polymer-chemical developments in clinical dental polymer materials: Enamel–dentin adhesives and restorative composites
N. Moszner (2012)
Ester-free thiol-ene dental restoratives--Part A: Resin development.
M. Podgórski (2015)
Characterization of a Low Shrinkage Dental Composite Containing Bismethylene Spiroorthocarbonate Expanding Monomer
Jing Fu (2014)
Factors involved in the development of polymerization shrinkage stress in resin-composites: a systematic review.
R. Braga (2005)
Development of low‐shrinkage composites based on novel crosslinking vinylcyclopropanes
Sven Tauscher (2017)
Evaluation of Difunctional Vinylcyclopropanes as Reactive Diluents for the Development of Low‐Shrinkage Composites
Yohann Catel (2017)
Comparison between a silorane-based composite and methacrylate-based composites: shrinkage characteristics, thermal properties, gel point and vitrification point.
Bo-tao Gao (2012)
Allyl sulfides and α‐substituted acrylates as addition–fragmentation chain transfer agents for methacrylate polymer networks
S. Ligon (2016)
Shrinkage properties of a modified dental resin composites containing a novel spiro-orthocarbonate expanding monomer
Xiang Sun (2011)
Stress relaxation via addition-fragmentation chain transfer in high T(g), high conversion methacrylate-based systems.
H. Y. Park (2012)
Synthesis and radical polymerization of 2‐vinylcyclopropanes
N. Moszner (2000)

This paper is referenced by
Semantic Scholar Logo Some data provided by SemanticScholar