Synthesis and evaluation of novel dental monomer with branched carboxyl acid group

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.

Section: Methodsmentioning

confidence: 99%

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

et al. 2018

Acta Biomaterialia

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“…Mixtures of monomers/photoinitiators are prepared in a brown glass vial under amber light. The preparation of adhesive formulations has been reported Previously [16]. …”

Section: Methodsmentioning

confidence: 99%

“…The experimental protocol for the water sorption analyses has been reported [16,34]. In brief, water sorption and solubility were measured using rectangular beam specimens (1 mm × 1 mm × 15 mm).…”

Section: Methodsmentioning

confidence: 99%

“…The LA damages the adjacent tooth surface by demineralization. Although numerous monomers have been investigated [10–16], the lack of dentin adhesives that are both effective and durable continues to be a major problem in restorative dentistry. Different strategies have been developed to enhance the hydrolytic stability of dentin adhesive resins.…”

Section: Introductionmentioning

confidence: 99%

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Compositional design and optimization of dentin adhesive with neutralization capability

et al. 2015

Journal of Dentistry

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Objectives The objective of this work was to investigate the polymerization behavior, neutralization capability, and mechanical properties of dentin adhesive formulations with the addition of the tertiary amine co-monomer, 2-N-morpholinoethyl methacrylate (MEMA). Methods A co-monomer mixture based on HEMA/BisGMA (45/55, w/w) was used as a control adhesive. Compared with the control formulation, the MEMA-containing adhesive formulations were characterized comprehensively with regard to water miscibility of liquid resin, water sorption and solubility of cured polymer, real-time photopolymerization kinetics, dynamic mechanical analysis (DMA), and modulated differential scanning calorimetry (MDSC). The neutralization capacity was characterized by monitoring the pH shift of 1 mM lactic acid (LA) solution, in which the adhesive polymers were soaked. Results With increasing MEMA concentrations, experimental copolymers showed higher water sorption, lower glass transition temperature and lower crosslinking density compared to the control. The pH values of LA solution gradually increased from 3.5 to about 6.0–6.5 after 90 days. With the increase in crosslinking density of the copolymers, the neutralization rate was depressed. The optimal MEMA concentration was between 20 and 40 wt%. Conclusions As compared to the control, the results indicated that the MEMA-functionalized copolymer showed neutralization capability. The crosslinking density of the copolymer networks influenced the neutralization rate.

“…The procedure to prepare the resin formulations has been reported[26–28]. The formulations consisted of HEMA and BisGMA with a mass ratio of 45/55, which is similar to widely used commercial dentin adhesives.…”

Section: Methodsmentioning

confidence: 99%

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

et al. 2015

JOM

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A new tertiary amine co-initiator (TUMA) containing three methacrylate-urethane groups was synthesized for application in dentin adhesives. The photopolymerization kinetics and leaching of unreacted components from methacrylate-based dental polymers formulated with this new co-initiator were determined. The newly synthesize co-initiator showed good chemical stability and decreased amine release from the initiator system. This study provides important information for the future development of biocompatible dentin adhesives/composites.