Recent Applications of the (TMS)3SiH Radical-Based Reagent

Chatgilialoglu, Chryssostomos; Lalevée, Jacques

doi:10.3390/molecules17010527

Cited by 92 publications

(62 citation statements)

References 110 publications

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“…In the literature, the TTMSS-based radicals were reported to possess outstanding reactivity and new photoinitiating systems have been proposed based on TTMSS [19–25]. In the present work, the maximum polymerization rates of methacrylate-based dentin adhesive were reduced dramatically by TTMSS.…”

Section: Discussionmentioning

confidence: 50%

“…It has been reported that the polymerization profiles in the presence of TTMSS for acrylate were better than that obtained in the presence of EDMAB. The profiles showed an increase of both the polymerization rates and final conversions [25]. Based on these results, TTMSS was selected as a co-initiator in the current investigation.…”

Section: Discussionmentioning

confidence: 99%

“…Nearly 20 years later, the Chat-gilialoglu laboratory discovered that TTMSS could serve as a radical-based agent [17,18]. Recently, the TTMSS radical has been characterized for applications in photoinitiation systems by Lalevee et al [19–25]. Lalavee and colleagues reported that TTMSS had the following attributes: (1) a high inherent reactivity for the addition to double bonds, and (2) a low ionization potential which is associated with an oxidation process and the formation of silylium cations.…”

Section: Introductionmentioning

confidence: 99%

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Tris(trimethylsilyl)silane as a co-initiator for dental adhesive: Photo-polymerization kinetics and dynamic mechanical property

Song

et al. 2016

Dental Materials

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Objectives The purpose of this study was to evaluate the polymerization behavior of a model dentin adhesive with tris(trimethylsilyl)silane (TTMSS) as a co-initiator, and to investigate the polymerization kinetics and mechanical properties of copolymers in dry and wet conditions. Methods A co-monomer mixture based on HEMA/BisGMA (45/55, w/w) was used as a model dentin adhesive. The photoinitiator system included camphorquinone (CQ) as the photosensitizer and the co-initiator was ethyl-4-(dimethylamino) benzoate (EDMAB) or TTMSS. Iodonium salt, diphenyliodonium hexafluorophosphate (DPIHP) serving as a catalyst, was selectively added into the adhesive formulations. The control and the experimental formulations were characterized with regard to the degree of conversion (DC) and dynamic mechanical properties under dry and wet conditions. Results In two-component photoinitiator system (CQ/TTMSS), with an increase of TTMSS concentration, the polymerization rate and DC of C═C double bond increased, and showed a dependence on the irradiation time and curing light intensity. The copolymers that contained the three-component photoinitiator system (CQ/TTMSS/DPIHP) showed similar dynamic mechanical properties, under both dry and wet conditions, to the EDMAB-containing system. Significance The DC of formulations using TTMSS as co-initiator showed a strong dependence on irradiation time. With the addition of TTMSS, the maximum polymerization rate can be adjusted and the network structure became more homogenous. The results indicated that the TTMSS could be used as a substitute for amine-type co-initiator in visible-light induced free radical polymerization of methacrylate-based dentin adhesives.

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Section: Discussionmentioning

confidence: 50%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Tris(trimethylsilyl)silane as a co-initiator for dental adhesive: Photo-polymerization kinetics and dynamic mechanical property

Song

et al. 2016

Dental Materials

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“…to connect with the oxygen on the epoxy group to form hydroxyl group (R-OH), which makes the C-O on the epoxy group break to proceed the epoxy ring-opening reaction [26]. The opened epoxy rings can, in turn, connect each other, and the bond can continue to grow, so that the epoxy monomers can form polymer structure through ring-opening reaction [27,28]. This reaction will be terminated by adding in terminator or hydrogen ions completely consumed only.…”

Section: Resultsmentioning

confidence: 99%

Incompatible hazard investigation of a cycloaliphatic epoxy resin using green analytical method

Tsai

Lin

Tong

et al. 2015

J Therm Anal Calorim

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A green analytical method was applied to evaluate the incompatible hazard for 3,4-epoxycyclohexane methyl-3 0 4 0 -epoxycyclohexyl-carboxylate (EEC) mixed with its synthetic materials. During the manufacturing process, numerous accidents of human poisoning, explosion, or fire have been reported due to the chemical's incompatible reaction. A calorimetric application and product's analysis approach have been employed to obtain related information for the incompatible hazard investigations of chemicals. This study also used nonlinear regression analysis to establish a kinetic model. The results proved that H 2 SO 4 can cause an abnormal curing reaction and release significant amounts of heat of the curing reaction for EEC, increasing the occurrence probability of accidents.Keywords Calorimetric application Á Curing reaction Á 3,4-Epoxycyclohexane methyl-3 0 4 0 -epoxycyclohexylcarboxylate (EEC) Á Kinetic model Á Product's analysis approach List of symbols APre-exponential factor (m 3 mol -1 s -1 ) E a Apparent activation energy (kJ mol -1 ) k 0 Frequency factor (m 3 mol -1 s -1 ) n i Reaction order of the stage, dimensionless,Autocatalytic constant, dimensionless da/dt Conversion rate (s -1 ) DH c Heat of curing reaction (kJ kg -1 )Greek letters a Degree of conversion, dimensionless b Scanning rate (°C min -1 )

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“…Silane is reported to be more efficient than an amine in FRP or free radical promoted cationic polymerization (FRPCP). 37–40 For the TTMSS silyl radical, a high reactivity with addition rate constant ( k add ~ 2:2×10 7 M −1 s −1 ) to methylacrylate was noted 38 . For the EDMAB generated radical, this value was 5 × 10 5 M −1 s −1 .…”

Section: Discussionmentioning

confidence: 98%

Development of methacrylate/silorane hybrid monomer system: Relationship between photopolymerization behavior and dynamic mechanical properties

Song

et al. 2015

J Biomed Mater Res

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Resin chemistries for dental composite are evolving as noted by the introduction of silorane-based composites in 2007. This shift in the landscape from methacrylate-based composites has fueled the quest for versatile methacrylate-silorane adhesives. The objective of this study was to evaluate the polymerization behavior and structure/property relationships of methacrylate-silorane hybrid systems. Amine compound ethyl-4-(dimethylamino) benzoate (EDMAB) or silane compound tris(trimethylsilyl) silane (TTMSS) was selected as coinitiators. The mechanical properties of the copolymer were improved significantly at low concentrations (15, 25, or 35 wt %) of silorane when EDMAB was used as coinitiator. The rubbery moduli of these experimental copolymers were increased by up to 260%, compared with that of the control (30.8 ± 1.9 MPa). Visible phase separation appeared in these formulations if the silorane concentrations in the formulations were 50–75 wt %. The use of TTMSS as coinitiator decreased the phase separation, but there was a concomitant decrease in mechanical properties. In the neat methacrylate formulations, the maximum rates of free-radical polymerization with EDMAB or TTMSS were 0.28 or 0.06 s−1, respectively. In the neat silorane resin, the maximum rates of cationic ring-opening polymerization with EDMAB or TTMSS were 0.056 or 0.087 s−1, respectively. The phase separation phenomenon may be attributed to differences in the rates of free-radical polymerization of methacrylates and cationic ring-opening polymerization of silorane. In the hybrid systems, free-radical polymerization initiated with EDMAB led to higher crosslink density and better mechanical properties under dry/wet conditions. These beneficial effects were, however, associated with an increase in heterogeneity in the network structure.

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Recent Applications of the (TMS)3SiH Radical-Based Reagent

Cited by 92 publications

References 110 publications

Tris(trimethylsilyl)silane as a co-initiator for dental adhesive: Photo-polymerization kinetics and dynamic mechanical property

Tris(trimethylsilyl)silane as a co-initiator for dental adhesive: Photo-polymerization kinetics and dynamic mechanical property

Incompatible hazard investigation of a cycloaliphatic epoxy resin using green analytical method

Development of methacrylate/silorane hybrid monomer system: Relationship between photopolymerization behavior and dynamic mechanical properties

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