Visible‐Light Initiated Free‐Radical/Cationic Ring‐Opening Hybrid Photopolymerization of Methacrylate/Epoxy: Polymerization Kinetics, Crosslinking Structure, and Dynamic Mechanical Properties

Ge, Xueping; Ye, Qiang; Song, Linyong; Misra, Anil; Spencer, Paulette

doi:10.1002/macp.201400506

Cited by 35 publications

(21 citation statements)

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“…Real-time in situ monitoring of the photopolymerization of the adhesive formulations was performed using an infrared spectrometer (Spectrum 400 Fourier transform infrared spectrophotometer, Perkin-Elmer, Waltham, MA) at a resolution of 4 cm −1 [17,18,36,37]. One drop of adhesive solution was placed on the diamond crystal top-plate of an attenuated total reflectance (ATR) accessory (Pike, GladiATR, Pike Technology, Madison, WI) and covered with a mylar film.…”

Section: Methodsmentioning

confidence: 99%

Effect of crosslinking density of polymers and chemical structure of amine-containing monomers on the neutralization capacity of dentin adhesives

Song

et al. 2015

Dental Materials

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Objectives Neutralization of the acidic micro-environment at the tooth/material interface is expected to provide enhanced durability for dental composite restorations. The objective of this study is to explore the effect of amine-containing monomer formulations and the crosslinking density of the resultant polymers on the neutralization capacity. Materials and methods The co-monomer system was varied systematically to obtain different proportions of Bisphenol A glycerolate dimethacrylate (BisGMA) and 2-hydroxyethyl methacrylate (HEMA), while maintaining a constant amount of amine-containing methacrylate monomer. A series of amine-containing monomers covering a range of pKa values were examined. Crosslinking density of formed copolymers was controlled by adjusting the weight content of the dimethacrylate monomer BisGMA. Lactic acid (LA) was used as a probe to analyze the effectiveness of the basic polymers to neutralize acid. The neutralization capacity of each amine-containing crosslinked copolymer was characterized by measuring pH as a function of time when the specimens were soaked in 1-mM LA solution, and the results were compared to the control formulations composed solely of BisGMA and HEMA. Polymer surfaces were examined using the methyl orange (MO) assay to quantify the amount of accessible amine groups. Results For each amine-containing crosslinked co-polymer, the neutralization capacity is enhanced by decreasing crosslinking density (e.g., by reducing BisGMA concentration in the formulation). In addition, more amine groups were accessible when crosslinking density was decreased. For different amine-containing polymers with the same BisGMA concentration, the neutralization capacity is higher when the amino monomers with higher pKa values were used in the formulations. Significance This is the first time that the neutralization capacity based on crosslinked dental polymers has been studied. The information is important for future development of durable dentin adhesives.

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Section: Methodsmentioning

confidence: 99%

Effect of crosslinking density of polymers and chemical structure of amine-containing monomers on the neutralization capacity of dentin adhesives

Song

et al. 2015

Dental Materials

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“…The rheological viscosity of composites shows a significant increase with the filler content as well as prepolymerized monomers. The resin viscosity defines the mobility of the CQ and the time to generate a reasonable number of free radicals to promote the polymerization . Thus, the decrease in free radicals can generate a more linear polymeric network structure with lower crosslinking density and, consequently, a composite resin with a lower Knoop microhardness …”

Section: Discussionmentioning

confidence: 99%

Light curing and ratio of glass/fumed silica fillers on degree of conversion and mechanical properties of experimental composite resins

Prezotto

Silva

Vitti

et al. 2018

J of Applied Polymer Sci

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This study evaluated the degree of conversion and mechanical properties of experimental composite resins made with different fillers and light‐curing methods. All composites had the same organic matrix (40% wt) and photoinitiator system (1.2% wt). Experimental composite groups were divided according to ratio (%) of silanated ground glass (0.5 μm) (BaAlSi) and fumed silica (SiO2): 100/0, 90/10, 80/20, and 70/30. Light‐emitting diode light was used in the continuous, soft‐start, and pulse‐delay modes (n = 10). Degree of conversion was determined using attenuated total reflectance–Fourier transform infrared spectroscopy. Flexural strength and modulus were obtained using a universal testing machine, and Knoop microhardness was measured in a Knoop indenter. The data were subjected to a two‐way ANOVA and Tukey's post hoc test (α = 0.05). Continuous‐light exposure of the 100/0 group produced the highest degrees of conversion. Soft‐start exposure of the 70/30 groups produced the highest Knoop microhardness. The pulse‐delay method produced the lowest flexural strength and modulus values. The 100/0 and 70/30 groups had the lowest flexural strength and flexural modulus, respectively. Application of continuous‐light output with composite resins containing a ratio of 80/20 (BaAlSi/SiO2) fillers generated the best results regarding the degree of conversion and mechanical properties. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019, 136, 47008.

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“…The kinetic data were converted to Rp/[M] 0 by taking the first derivative of the time versus conversion curve[28, 32], where Rp and [M] 0 are the rate of polymerization and the initial monomer concentration, respectively.…”

Section: Methodsmentioning

confidence: 99%

“…The preparation of the polymer specimens has been reported[11–14, 25, 32–34]. In brief, round beams with a diameter of 1 mm and a length of at least 15 mm were prepared by injecting the adhesive formulations into glass-tubing molds (Fiber Optic Center, Inc., part no.…”

Section: Methodsmentioning

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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Visible‐Light Initiated Free‐Radical/Cationic Ring‐Opening Hybrid Photopolymerization of Methacrylate/Epoxy: Polymerization Kinetics, Crosslinking Structure, and Dynamic Mechanical Properties

Cited by 35 publications

References 95 publications

Effect of crosslinking density of polymers and chemical structure of amine-containing monomers on the neutralization capacity of dentin adhesives

Effect of crosslinking density of polymers and chemical structure of amine-containing monomers on the neutralization capacity of dentin adhesives

Light curing and ratio of glass/fumed silica fillers on degree of conversion and mechanical properties of experimental composite resins

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

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