Onium salt improves the polymerization kinetics in an experimental dental adhesive resin

Ogliari, Fabrício Aulo; Ely, Caroline; Petzhold, César Liberato; Demarco, Flávio Fernando; Piva, Evandro

doi:10.1016/j.jdent.2007.04.001

Cited by 88 publications

(111 citation statements)

References 15 publications

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“…At the same time, with the addition of DIPHP, there was no significant difference in DC or polymerization rate with an increase in irradiation intensity. Although, the reaction mechanism using a three-component PI system is more complex, it was postulated that these results can be attributed to the generation of higher activity phenyl free radical [62] (see Scheme 1). …”

Section: Discussionmentioning

confidence: 99%

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: 99%

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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“…This free radical reacts with tertiary amines present in the composite, making it an efficient photo-initiator for polymerization. 35 However, these free radicals formed can then react with remaining tertiary amines, subtracting a proton and generating a new amine radical. 36 Thermally or photo-chemically induced color alteration has generally been attributed to the oxidation of this amine accelerator.…”

Section: Discussionmentioning

confidence: 99%

Color stability of silorane-based composites submitted to accelerated artificial ageing—An in situ study

Pires‐de‐Souza

Garcia

Roselino

et al. 2011

Journal of Dentistry

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“…The durability of composite restorations does not, however, match that of dental amalgam[2–6]. The average clinical lifetime of posterior composite resin restorations is just 5.7 years due to secondary decay or fracture [7, 8]. The dominant reason for failure of composite restorations is secondary decay and clinically, the failure occurs most often at the composite/tooth interface [9, 10].…”

Section: Introductionmentioning

confidence: 99%

“…CQ is a light absorbing photosensitizer and the amine compound is an electron donor serving as co-initiator. Recently, a third component (often a daryliodonium or sulfonium salt) is applied into the CQ/amine photoinitiating system to improve the visible light induced photopolymerization [7, 16–20]. …”

Section: Introductionmentioning

confidence: 99%

Probing the dual function of a novel tertiary amine compound in dentin adhesive formulations

Song

et al. 2016

Dental Materials

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Objectives A novel tertiary amine compound containing three methacrylate-urethane groups was synthesized for application in dentin adhesives. The synthesis, photopolymerization kinetics, and leaching were examined in an earlier study using this novel compound as the co-initiator (0.5 and 1.75 wt% based on the total resin mass). The objective of this work was to investigate the potential of TUMA (8-(2-(((2-(methacryloyloxy)ethyl)carbamoyl)oxy)propyl)-6,10-dimethyl-4,12-dioxo-5,11-dioxa-3,8,13-triazapentadecane-1,15-diyl bis(2-methylacrylate)) to serve simultaneously as a co-initiator and co-monomer (15 to 45 wt% based on the total resin mass) in dentin adhesive formulations. The polymerization kinetics, water sorption and dynamic mechanical properties of these novel formulations were determined. Materials and method The monomer system contained Bisphenol A glycerolate dimethacrylate (BisGMA), 2-hydroxyethylmethacrylate (HEMA) and TUMA (synthesized in our lab) at the mass ratio of 45/55-x/x. Two photoinitiator (PI) systems were compared. One initiator system contains three components: camphorquinone (CQ), diphenyliodonium hexafluorophosphate (DPIHP) and ethyl-4-(dimethylamino) benzoate (EDMAB) and the second initiator system contains CQ and DPIHP. The control adhesive formulations are: C0-3: HEMA/BisGMA 45/55 w/w and 3-component PI and C0-2: HEMA/BisGMA 45/55 w/w and 2-component PI. These controls were used as a comparison to the experimental adhesive resins (Ex-3 or Ex-2), in which x represents the weight percentage of synthesized co-monomer (TUMA) to replace part of BisGMA. The control and experimental adhesive formulations were photo-polymerized and compared with regard to the degree of conversion (DC), polymerization rate (Rp), water sorption and dynamic mechanical analysis (DMA) under both dry and wet conditions. Results C0-3 and Ex-3 formulations had similar DC, while the DC of Ex-2 formulation was higher than C0-2. The DC was similar when comparing the two- component with the three-component photoinitiator system when TUMA was used at the same concentration. DMA under dry conditions shows higher rubbery storage modulus for all experimental formulations, while storage modulus at rubbery region under wet conditions was decreased as compared with control (C0-3). There was no statistically significant difference for the DMA results under both dry and wet conditions when comparing two- and three-component initiator systems with the same TUMA concentration. Significance The newly synthesized TUMA could serve simultaneously as a co-monomer and co-initiator in the absence of commercial co-initiator. This study provides information for the future development of new co-monomer/co-initiator for dentin adhesives and dental composites.

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Onium salt improves the polymerization kinetics in an experimental dental adhesive resin

Cited by 88 publications

References 15 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

Color stability of silorane-based composites submitted to accelerated artificial ageing—An in situ study

Probing the dual function of a novel tertiary amine compound in dentin adhesive formulations

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