Synthesis and Evaluation of a Novel Co-Initiator for Dentin Adhesives: Polymerization Kinetics and Leachables Study

Ge, Xueping; Ye, Qiang; Song, Linyong; Laurence, Jennifer S.; Spencer, Paulette

doi:10.1007/s11837-015-1335-6

Cited by 18 publications

(23 citation statements)

References 36 publications

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“…The new co-monomers, SNE/SNM, were synthesized based on the following procedures [48]. Briefly, to a 250–mL, round bottom flask, fitted with a magnetic stirrer and N 2 –purging, MPD (4.20 g, 25 mmol), DBTL (20 µL) and tetrahydrofuran (THF, 50 mL) were added.…”

Section: Methodsmentioning

confidence: 99%

Fabrication of hybrid crosslinked network with buffering capabilities and autonomous strengthening characteristics for dental adhesives

Song

et al. 2018

Acta Biomaterialia

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Ingress of bacteria and fluids at the interfacial gaps between the restorative composite biomaterial and the tooth structure contribute to recurrent decay and failure of the composite restoration. The inability of the material to increase the pH at the composite/tooth interface facilitates the outgrowth of bacteria. Neutralizing the microenvironment at the tooth/composite interface offers promise for reducing the damage provoked by cariogenic and aciduric bacteria. We address this problem by designing a dental adhesive composed of hybrid network to provide buffering and autonomous strengthening simultaneously. Two amino functional silanes, 2-hydroxy-3-morpholinopropyl (3-(triethoxysilyl)propyl) carbamate and 2-hydroxy-3-morpholinopropyl (3-(trimethoxysilyl)propyl) carbamate were synthesized and used as co-monomers. Combining free radical initiated polymerization (polymethacrylate-based network) and photoacid-induced sol-gel reaction (polysiloxane) results in the hybrid network formation. Resulting formulations were characterized with regard to real-time photo-polymerization, water sorption, leached species, neutralization, and mechanical properties. Results from real-time FTIR spectroscopic studies indicated that ethoxy was less reactive than methoxy substituent. The neutralization results demonstrated that the methoxy-containing adhesives have acute and delayed buffering capabilities. The mechanical properties of synthetic copolymers tested in dry conditions were improved via condensation reaction of the hydrolyzed organosilanes. The leaching from methoxy containing copolymers was significantly reduced. The sol-gel reaction provided a chronic and persistent reaction in wet condition-performance that offers potential for reducing secondary decay and increasing the functional lifetime of dental adhesives.

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Section: Methodsmentioning

confidence: 99%

Fabrication of hybrid crosslinked network with buffering capabilities and autonomous strengthening characteristics for dental adhesives

Song

et al. 2018

Acta Biomaterialia

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“…Our former investigation suggested that TUMA is a promising co-initiator[23], which offers comparable photopolymerization efficiency and prevents amine leaching from the adhesive polymers. Since there are three-methacrylate groups in each TUMA molecule, it is very likely that it could serve as a crosslinkable comonomer in dental resins.…”

Section: Discussionmentioning

confidence: 99%

“…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)) was synthesized in our lab and used as the co-monomer with HEMA and BisGMA [23]. Based on our previous studies, [12, 15, 24–27] camphorquinone (CQ), ethyl-4-(dimethylamino) benzoate (EDMAB) and diphenyliodonium hexafluorophosphate (DPIHP) were used as a three-component-photoinitiator system.…”

Section: Methodsmentioning

confidence: 99%

“…A tertiary amine co-initiator (TUMA) containing three methacrylate-urethane groups was synthesized in our laboratory for application in dentin adhesives[23]. The results from an earlier study showed comparable degree of conversion with formulations containing 0.5% or 1.75% TUMA as compared to commercial amine co-initiators ethyl-4-(dimethylamino) benzoate (EDMAB) and 2-(dimethylamino) ethyl methacrylate (DMAEMA).…”

Section: Introductionmentioning

confidence: 99%

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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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“…Therefore, DC, VS, WS, SL, FS, FM, and fracture energy of new FUDMA/ TEGDMA resin system were investigated and compared with Bis-GMA/TEGDMA resin system. The DC of a resin depends on the chemical structure of the monomer (Sideridou et al, 2002), nature and concentration of photoinitiation system (He et al, 2008;Shin and Rawls, 2009;Ge et al, 2015), and polymerization conditions like atmosphere (Chen et al, 2012), temperature (Jafarzadeh-Kashi et al, 2014), light intensity (Jafarzadeh-Kashi et al, 2014;Lovell et al, 2003), irradiation time (Tarle et al, 2015), curing methods (Costa et al, 2011) and so on. In this research, the difference in DC between FUDMA/TEGDMA and Bis-GMA/ TEGDMA resins was due to the difference in structure between FUDMA and Bis-GMA, for all the other conditions were kept the same with each other.…”

Section: Discussionmentioning

confidence: 99%

Synthesis of fluorinated dimethacrylate monomer and its application in preparing Bis-GMA free dental resin

Yin

Guo

Liu

et al. 2015

Journal of the Mechanical Behavior of Biomedical Materials

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Synthesis and Evaluation of a Novel Co-Initiator for Dentin Adhesives: Polymerization Kinetics and Leachables Study

Cited by 18 publications

References 36 publications

Fabrication of hybrid crosslinked network with buffering capabilities and autonomous strengthening characteristics for dental adhesives

Fabrication of hybrid crosslinked network with buffering capabilities and autonomous strengthening characteristics for dental adhesives

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

Synthesis of fluorinated dimethacrylate monomer and its application in preparing Bis-GMA free dental resin

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