Browse
Submit Data
Databases
API
Help

Dataset Information

16 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis and characterization of new hydrolytic-resistant dental resin adhesive monomer HMTAF.

ABSTRACT: Hydrolytic and enzymatic degradation of resin adhesives over time has been mainly attributed to secondary caries formation of methacrylate-based tooth-colored resin-based composite restorations. Ability of resin adhesive monomers to infiltrate into demineralized dentin forming stiff polymer matrix and potentially bonding to tooth structure is also a crucial property. The only commercially available antibacterial monomer, 12-methacryloyloxydodecyl pyridinium bromide (MDPB), is a quaternary ammonium methacrylate. This methacrylate monomer undergoes hydrolytic degradation, and could not bond to tooth structure. In this study, a new hydrolytic resistant monomer HMTAF was synthesized. It is methacrylamide-based monomer that, unlike methacrylate, is highly resistant to hydrolysis. Its molecular structure has particular functional groups; quaternary ammonium fluoride salt with potential antibacterial fluoride-releasing activity, hydroxyl and amide group with hydrogen bonding potential to dentin collagen. Hydroxyl group also increases monomer hydrophilicity for better penetration into water-saturated dentin and sufficient resin-dentin bond. The synthesized HMTAF and its polymer showed no hydrolytic degradation in acidic environment, while MDPB and its polymer were partially decomposed under this challenge. The conversion of monomer HMTAF to polymer was illustrated by FT-IR. The results indicated that HMTAF is highly resistant to hydrolysis, polymerizable and non-cytotoxic to Vero cell lines. It is a potential monomer to be incorporated into resin adhesives for improving hydrolytic and enzymatic resistance.

SUBMITTER: Decha N

PROVIDER: S-EPMC6522974 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Probing the neutralization behavior of zwitterionic monomer-containing dental adhesive.

Project description:To investigate the polymerization kinetics, neutralization behavior, and mechanical properties of amine-functionalized dental adhesive cured in the presence of zwitterionic monomer, methacryloyloxyethyl phosphorylcholine (MPC).The control adhesive was a mixture based on HEMA/BisGMA/2-N-morpholinoethyl methacrylate (MEMA) (40/30/30, w/w/w). The control and experimental formulations containing MPC were characterized with regard to water miscibility of liquid resins, photopolymerization kinetics, water sorption and solubility, dynamic mechanical properties and leachables from the polymers (aged in ethanol). The neutralization behavior of the adhesives was determined by monitoring the pH of lactic acid (LA) solution.The water miscibility decreased with increasing MPC amount. The water sorption of experimental copolymer specimen was greater than the control. The addition of 8wt% water led to improved photo-polymerization efficiency for experimental formulations at MPC of 2.5 and 5wt%, and significant reduction in the cumulative amounts of leached HEMA, BisGMA, and MEMA, i.e. 90, 60 and 50% reduction, respectively. The neutralization rate of MPC-containing adhesive was faster than control. The optimal MPC concentration in the formulations was 5wt%.Incompatibility between MEMA and MPC led to a decrease in water miscibility of the liquid resins. Water (at 8wt%) in the MPC-containing formulations (2.5-5wt% MPC) led to higher DC, faster RPmax and significant reduction in leached HEMA, BisGMA, and MEMA. The neutralization rate was enhanced with the addition of MPC in the amine-containing formulation. Promoting the neutralization capability of dentin adhesives could play an important role in reducing recurrent decay at the composite/tooth interface.

| S-EPMC5480395 | biostudies-literature

Preparation of a highly crosslinked biosafe dental nanocomposite resin with a tetrafunctional methacrylate quaternary ammonium salt monomer.

Project description:The design of antimicrobial dental nanocomposite resin to prevent secondary dental caries and minimize biosafety problems is an important endeavor with both fundamental and practical implications. In the present work, a novel tetrafunctional methacrylate-based polymerizable quaternary ammonium monomer (TMQA) was synthesized with the aim of using it as an immobilized antibacterial agent in methacrylate dental composites, and its structure was characterized. The antibacterial action of TMQA and polymerized resin specimens against suspected cariogenic bacteria Streptococcus mutans were evaluated. Furthermore, the double bond conversion, contact angle, water sorption, solubility, heterogeneity, and crosslink density of the experimental resins with different concentrations of TMQA were investigated. CCK-8 and real-time cell analyses were used to evaluate the cytotoxicity of the experimental resins. The results showed that TMQA was successfully synthesized and had strong antibacterial properties against Streptococcus mutans. The experimental resins with different concentrations of TMQA had a similar degree of conversion and contact angle to the neat resin. With the addition of 4% TMQA to the resins, water absorption and solubility were reduced while their heterogeneity and crosslink density increased. The cell viability of each experimental group was similar to that of the neat resin group and was higher than that of the commercial adhesive single bond 2 group. Therefore, TMQA can be used to impart antibacterial properties to resins and increase the crosslink density of dental resin composites.

| S-EPMC9076464 | biostudies-literature

Multifunctional monomer acts as co-initiator and crosslinker to provide autonomous strengthening with enhanced hydrolytic stability in dental adhesives.

Project description:ObjectiveThe purpose of this study was to evaluate a new synthesized multifunctional monomer, aminosilane functionalized methacrylate (ASMA), containing polymerizable methacrylate, tertiary amine, and methoxysilane functionalities in dental adhesive formulations, and to investigate the polymerization kinetics, leachates, thermal and mechanical properties of copolymers.MethodsAdhesive contained HEMA/BisGMA (45/55, w/w) was used as a control, and mixtures based on HEMA/BisGMA/ASMA at the mass ratio of 45/(55-x)/x were used as experimental adhesive. Adhesives were characterized with regard to water miscibility, photo-polymerization behavior (Fourier transform infrared spectroscopy, FTIR), leached co-monomers (high performance liquid chromatography, HPLC), thermal properties (modulated differential scanning calorimeter, MDSC), and mechanical properties (dynamic mechanical analyzer, DMA). Stress relaxation times and the corresponding moduli, obtained from stress relaxation tests, are used in a simulated linear loading case.ResultsAs compared to the control, ASMA-containing adhesives showed higher water miscibility, lower viscosity, improved monomer-to-polymer conversion, significantly greater Tg and rubbery modulus. HPLC results indicated a substantial reduction of leached HEMA (up to 85wt%) and BisGMA (up to 55wt%) in ethanol. The simulation reveals that the ASMA-containing adhesive becomes substantially stiffer than the control.SignificanceASMA monomer plays multiple roles, i.e. it serves as both a co-initiator and crosslinker while also providing autonomous strengthening and enhanced hydrolytic stability in the adhesive formulations. This multifunctional monomer offers significant promise for improving the durability of the adhesive at the composite/tooth interface.

| S-EPMC7012759 | biostudies-literature

Preparation of Dental Resins Resistant to Enzymatic and Hydrolytic Degradation in Oral Environments.

Project description:The short average service life of traditional dental composite restorative materials and increasing occurrence of secondary caries adjacent to composite restorations and sealants are necessitating the development of new, longer lasting compositions. Novel monomers and their polymers, reinforcing fillers, and adhesive components are needed. The goal of this research is to develop resin systems for use in restorations, sealants, and other dental services that are superior in properties and endurance to currently used bisphenol A glycidyl dimethacrylate/triethylene glycol dimethacrylate (Bis-GMA/TEGDMA) and urethane-dimethacrylate products. Ether-based monomers and their polymers that were not susceptible to enzymatic or hydrolytic degradation were prepared and characterized. They showed no degradation under hydrolytic and enzymatic challenges, whereas the hydrolysis of ester links weakened contemporary resins within 16 days under these challenges. The success of the ether-based materials is promising in making durable systems that are subjected to long-term biochemical and hydrolytic challenges in oral environments.

| S-EPMC4788384 | biostudies-literature

Nano-CT as tool for characterization of dental resin composites.

Project description:Technological advances have made it possible to examine dental resin composites using 3D nanometer resolution. This investigation aims to characterize existing dental nano-hybrid and micro-hybrid resin composites through comparing and contrasting nano-computed tomography (nano-CT) with micro-CT and high-resolution SEM images. Eight commercially available and widely used dental resin composites, 2 micro-hybrid and 6 nano-hybrid were researched. Cured samples were examined and characterized using nano-CT (resolution 450 nm) and compared with micro-CT images (resolution 2 µm). Acquired images were reconstructed and image analysis was carried out to determine porosity and pore morphology. A comprehensive comparison of scanning micrograph images unsurprisingly revealed that the nano-CT images displayed greater detail of the ultrastructure of cured dental resin composites. Filler particle diameters and its volumes were lower when measured using nano-CT, porosity being higher where analysed at higher resolution. There were large variations between the examined materials. Fewer voids were found in Tetric EvoCeram and IPS Empress Direct, the smallest pores being found in Universal XTE and Tetric EvoCeram. Nano-CT was successfully used to investigate the morphology of dental resin composites and showed that micro-CT gives a lower porosity and pore size but overestimates filler particle size. There were large discrepancies between the tested composites. Evidence of porosities and pores within a specimen is a critical finding and it might have a detrimental effect on a material's clinical performance.

| S-EPMC7511412 | biostudies-literature

Impact of Irradiation on the Adhesive Performance of Resin-Based Dental Biomaterials: A Systematic Review of Laboratory Studies.

Project description:Head and neck cancers are a significant global health burden, with radiation therapy being a frequently utilized treatment. The aim of this systematic review was to provide a critical appraisal of laboratory studies that assessed the effect of irradiation on the adhesive performance of resin-based biomaterials. The analysis included 23 laboratory studies obtained from five databases, with most studies using human enamel, dentin, or both, and bonding procedures involving the fabrication of direct restorations, standardized specimens, bonding of orthodontic brackets, and luting of endodontic fiber posts. The protocols used for irradiation varied, with most studies exposing specimens made from extracted teeth to irradiation using cabinet irradiators to simulate treatment of head and neck cancer. The findings indicate that irradiation reduces the bond strength of dental adhesives and resin-based composites on flat, ground enamel and dentin specimens, with different adhesives and timing of irradiation having a significant impact on adhesive performance. Irradiation also increased microleakage in most studies. The effect of irradiation on marginal adaptation of direct resin-based composite restorations was inconclusive. This systematic review indicates that irradiation has detrimental effects on the adhesive performance of resin-based biomaterials and highlights the need for further clinical and laboratory studies evaluating the performance of adhesive materials and approaches to improve it.

| S-EPMC10095157 | biostudies-literature

Characteristics of 10-Methacryloyloxidecyl Dihydrogen Phosphate Monomer in Self-Etching Two-Bottled Dental Adhesive System: Comparison with Commercial Products.

Project description:Dentin bonding is a key in restorative dentistry. Here, we developed a self-etching two-bottle adhesive system containing 10-methacryloyloxidecyl dihydrogen phosphate monomer (MDP) and the physical, mechanical, and biocompatible properties were evaluated. The characteristics of MDP were analyzed using nuclear magnetic resonance (NMR). Tests for water sorption and solubility, the shear-bond strengths to dentin and enamel, and cytotoxicity were performed. The newly-blended experimental group showed the lowest thickness and water sorption and solubility values. The shear bond strength of enamel and dentin were comparable to control groups (the three other products were ClearfilTM, UniFil®, and AdheSE®). All test groups showed 60% of cell viability. In this study, the properties of the newly-synthesized adhesive are comparable with the others. The fundamental goal of this study is to get the MDP patent released, as it is intended for domestic production. For this purpose, this dentin adhesive was developed and compared with the commercial product.

| S-EPMC7475973 | biostudies-literature

Influence of Curing Mode on the Surface Energy and Sorption/Solubility of Dental Self-Adhesive Resin Cements.

Project description:This study investigated the influence of curing mode (dual- or self-cure) on the surface energy and sorption/solubility of four self-adhesive resin cements (SARCs) and one conventional resin cement. The degree of conversion (DC) and surface energy parameters including degree of hydrophilicity (DH) were determined using Fourier transform infrared spectroscopy and contact angle measurements, respectively (n = 5). Sorption and solubility were assessed by mass gain or loss after storage in distilled water or lactic acid for 60 days (n = 5). A linear regression model was used to correlate between the results (%DC vs. DH and %DC/DH vs. sorption/solubility). For all materials, the dual-curing consistently produced significantly higher %DC values than the self-curing (p < 0.05). Significant negative linear regressions were established between the %DC and DH in both curing modes (p < 0.05). Overall, the SARCs showed higher sorption/solubility values, in particular when immersed in lactic acid, than the conventional resin cement. Linear regression revealed that %DC and DH were negatively and positively correlated with the sorption/solubility values, respectively. Dual-curing of SARCs seems to lower the sorption and/or solubility in comparison with self-curing by increased %DC and occasionally decreased hydrophilicity.

| S-EPMC5459112 | biostudies-other

Synthesis and Characterization of Allyl Terpene Maleate Monomer.

Project description:Terpenes and their derivatives are sustainable, renewable chemicals that can be used as a complementary hydrocarbon. The exceptions are fossil-based feedstocks and lignin-based feedstocks. A simple method has been found to prepare allyl terpene maleate monomer by substitution reaction at lower reaction temperatures. Using terpenes from turpentine, maleic anhydride and allyl chloride as reactants, the synthesized monomer, terpene-diallyl maleate adduct, was prepared by D-A addition, hydrolysis, and substitution reaction. The resultant monomer was characterized for the first time. The synthesized product will be a versatile monomer and a very important intermediate, having broad application prospects. The synthesized monomer will replace similar aromatic compounds in certain applications because of its low-toxicity and sustainability. The synthesized monomer with two terminal olefin structures has great free radical polymerization potential, according to its physical and chemical properties and exploratory experimentation.

| S-EPMC6914792 | biostudies-literature

Hydrolysis-resistant and stress-buffering bifunctional polyurethane adhesive for durable dental composite restoration.

Project description:A new elastic polyurethane (PU) adhesive was reported in this study to improve the stability and durability of the dental adhesion interface. A polyurethane oligomer was synthesized by the solution polymerization method, and a diluent and solvent were added to prepare PU adhesives. The water sorption, water solubility, contact angle, thermal stability, degree of conversion and mechanical properties of the PU adhesives were evaluated. Experimental applications for tooth restoration (microtensile bond strength and microleakage) were also performed, and cytotoxicity test was carried out. The water sorption and solubility of the PU adhesives were significantly lower than those of three commercial adhesives. The microtensile bond strength of the PU adhesives was improved after thermocycling test, and the extent of microleakage was diminished when compared with that of commercial adhesives. Biocompatibility testing demonstrated that the PU adhesive was non-toxic to L929 fibroblasts. This study shows the ability of PU adhesive to improve the stability and durability of the dental adhesion interface and may refocus the attention of scientists from rigid bonding to flexible bonding for dental adhesion, and it sheds light on a new strategy for the stable and durable bonding interface of dentine adhesives.

| S-EPMC7428285 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data