Enhanced reduction of polymerization-induced shrinkage stress <i>via</i> combination of radical ring opening and addition fragmentation chain transfer

Schoerpf, Sebastian; Catel, Yohann; Moszner, Norbert; Gorsche, Christian; Liska, Robert

doi:10.1039/c8py01540f

Cited by 32 publications

(24 citation statements)

References 35 publications

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“…Moszner, Liska and coworkers investigated the photocuring of vinylcyclopropane-based composites as alternative to methacrylate-based dental fillings [ 51 , 52 , 53 ]. The synthetic focus was directed on various vinylcyclopropane monomers, which contain similar structural units like in commonly used acrylate-based monomers such as urethane dimethacrylate UDMA and tri(ethylene glycol) dimethacrylate TEGDMA ( Figure 8 ).…”

Section: Expanding Cycloalkanes and Cycloalkenesmentioning

confidence: 99%

“…Notably, in this context, bifunctional monomers, of which one of the two functionalities can be cured upon volumetric expansion, have been evaluated for applicability in novel product generations most recently. Prominent research foci comprise photopolymerizations with low or no volumetric shrinkage during curing [ 36 , 50 , 53 , 58 , 59 , 60 , 90 , 91 , 92 , 93 , 94 , 95 , 128 , 129 ], dental fillings with low or no volumetric shrinkage during curing [ 21 , 75 , 98 , 100 , 101 , 102 , 111 ] and the 3D printing with unrivaled alignment of the geometry of the printed object with the CAD drawing [ 51 , 73 ].…”

Section: Applicability Of Expanding Monomers In Novel Products Andmentioning

confidence: 99%

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Expanding Monomers as Anti-Shrinkage Additives

Marx

Wiesbrock

2021

Polymers

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Commonly, volumetric shrinkage occurs during polymerizations due to the shortening of the equilibrium Van der Waals distance of two molecules to the length of a (significantly shorter) covalent bond. This volumetric shrinkage can have severe influence on the materials’ properties. One strategy to overcome this volumetric shrinkage is the use of expanding monomers that show volumetric expansion during polymerization reactions. Such monomers exhibit cyclic or even oligocyclic structural motifs with a correspondingly dense atomic packing. During the ring-opening reaction of such monomers, linear structures with atomic packing of lower density are formed, which results in volumetric expansion or at least reduced volumetric shrinkage. This review provides a concise overview of expanding monomers with a focus on the elucidation of structure-property relationships. Preceded by a brief introduction of measuring techniques for the quantification of volumetric changes, the most prominent classes of expanding monomers will be presented and discussed, namely cycloalkanes and cycloalkenes, oxacycles, benzoxazines, as well as thiocyclic compounds. Spiroorthoesters, spiroorthocarbonates, cyclic carbonates, and benzoxazines are particularly highlighted.

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Section: Expanding Cycloalkanes and Cycloalkenesmentioning

confidence: 99%

Section: Applicability Of Expanding Monomers In Novel Products Andmentioning

confidence: 99%

Expanding Monomers as Anti-Shrinkage Additives

Marx

Wiesbrock

2021

Polymers

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“…The observed shrinkage stress evolves during polymerization reaction upon transitioning of the applied formulation from the liquid to solid-state (i.e., gel point) and is built up upon vitrification until the final conversion is reached. Before free radical photopolymerization, the monomers are situated at van der Waal's distance towards each other (approximately 3.4 Å) [104]. The occurring shrinkage stress upon gelation is partially due to the formation of covalent bonds between the respective monomers, where the revealing distance is only 1.5 Å [105].…”

Section: Monomers For Free Radical Photopolymerization Processes In Dmentioning

confidence: 99%

Moving Towards a Finer Way of Light-Cured Resin-Based Restorative Dental Materials: Recent Advances in Photoinitiating Systems Based on Iodonium Salts

Topa

Ortyl

2020

Materials

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The photoinduced polymerization of monomers is currently an essential tool in various industries. The photopolymerization process plays an increasingly important role in biomedical applications. It is especially used in the production of dental composites. It also exhibits unique properties, such as a short time of polymerization of composites (up to a few seconds), low energy consumption, and spatial resolution (polymerization only in irradiated areas). This paper describes a short overview of the history and classification of different typical monomers and photoinitiating systems such as bimolecular photoinitiator system containing camphorquinone and aromatic amine, 1-phenyl-1,2-propanedione, phosphine derivatives, germanium derivatives, hexaarylbiimidazole derivatives, silane-based derivatives and thioxanthone derivatives used in the production of dental composites with their limitations and disadvantages. Moreover, this article represents the challenges faced when using the latest inventions in the field of dental materials, with a particular focus on photoinitiating systems based on iodonium salts. The beneficial properties of dental composites cured using initiation systems based on iodonium salts have been demonstrated.

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“…Photo-rheometers have also been used to measure UV-curing kinetics in the past quarter of a century [4]. Real-time near infrared spectroscopy, equipped with a photo-rheometer (as developed by Liska's group), has advanced the kinetic study of normal force (shrinkage force) and double bond conversion [5][6][7][8][9][10][11]. A laser displacement sensor has been used in a controlled atmosphere to elucidate the degree of shrinkage, both in air and oxygen-free atmospheres [12].…”

Section: Introductionmentioning

confidence: 99%

Effects of Ultraviolet Intensity and Initial Thickness on Normal Force of Acrylic Ultraviolet Curable Resin

Taki

Sawa

2020

J. Photopol. Sci. Technol.

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Enhanced reduction of polymerization-induced shrinkage stress via combination of radical ring opening and addition fragmentation chain transfer

Abstract: The combination of vinylcyclopropanes with an ester-activated vinyl sulfonate ester in a light-induced radical polymerization shows high reactivity accompanied by a significant increase in conversion and it leads to an enhanced reduction of polymerization-induced shrinkage stress.

Cited by 32 publications

References 35 publications

Expanding Monomers as Anti-Shrinkage Additives

Expanding Monomers as Anti-Shrinkage Additives

Moving Towards a Finer Way of Light-Cured Resin-Based Restorative Dental Materials: Recent Advances in Photoinitiating Systems Based on Iodonium Salts

Effects of Ultraviolet Intensity and Initial Thickness on Normal Force of Acrylic Ultraviolet Curable Resin

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