Bisphenol A Dimethacrylate Research Articles

A novel intralamellar semi‐bioresorbable keratoprosthesis—Part A: Design conception, material perspective, and device manufacturing

AbstractCorneal diseases are a significant cause of visual impairment and blindness. The first‐line treatment for corneal opacity is penetrating keratoplasty (human donor cornea transplantation). At present, keratoprosthesis (KPro), an artificial cornea, is the last resort for correcting end‐stage corneal blindness and is usually supported by donor tissue. This article describes a new intralamellar tissue‐free KPro design concept and its preparation method. Wherein, an injection‐molding route is adopted to create a mechanically and structurally stable near‐KPro geometry using a photo‐polymerized poly(2‐hydroxyethyl methacrylate) (pHEMA) with 4% Bisphenol A dimethacrylate (BisMA) crosslinked (PC4) hydrogel composition. Prior to this, the physico‐mechanical properties of crosslinked hydrogels matching corneal tissue are identified, and the surface morphological characteristics of silk cocoon membranes are ascertained in choosing suitable KPro materials. Cytocompatibility tests on PC4 and silk‐incorporated PC4 hydrogels using rabbit corneal fibroblast cell‐line evidenced enhancement in cell growth on silk‐PC4 surfaces. Furthermore, near KPro geometry is surface‐profiled to create a one‐of‐a‐kind design with clear optics and a silk‐bioactivated composite‐based haptic‐flange hydrogel network containing site‐specific submillimeter‐scale perforations to improve tissue integration. Considering this unique KPro geometry, the optic‐haptic‐flange construct is a tissue‐free semi‐bioresorbable hydrogel device presumed to provide stability under the influence of intraocular pressure (IOP) and eyelid shear. Through this study, it is identified new KPro materials facilitate significant cytocompatibility while complimented with site‐specific novel design would offer tissue ingrowth with gradual resorption of silk, leaving behind a stable intralamellar tissue integrated with hydrogel when implanted in the corneal niche.

Non-monotonic effects of Bisphenol A Dimethacrylate on male mouse reproductive system and fertility leads to impaired conceptive performance

As an estrogenic agent, Bisphenol A Dimethacrylate (Bis-DMA) may incite alterations in both the reproductive tract and the neuroendocrine axis, and thus have the potential to affect the proper development, maturity and conceptive performance in animals. We investigated the consequences of 14 weeks of exposure to different concentrations of Bis-DMA on male mouse conceptive performance. Male mice were exposed to Bis-DMA (0, 0.1 mg/L, 1.0 mg/L or 10 mg/L) via drinking water, and the effects on fertility, reproductive organ weights, reproductive hormone levels, sperm counts and testicular histology were assessed. We clearly demonstrate that prolonged exposure of male mice to Bis-DMA negatively affects fertility and reproduction causing significant reductions in sperm counts, non-monotonic effects on serum LH and testosterone levels, increased seminal vesicle weights, lower number of embryonic implantations and viable fetuses, as well as, increased embryonal resorptions in females mated by Bis-DMA treated males. Furthermore, Bis-DMA caused abnormalities in testicular infrastructure with atrophic seminiferous tubules exhibiting intraepithelial vacuolization and disorganization, loss and shedding of germ cells into the lumen, and presence of apoptotic cells. Our data collectively suggest that Bis-DMA adversely affects male fertility and reproduction by interference with normal hormone signaling in the testis, inducing changes in testicular infrastructure and ultimately leading to impaired reproductive function and fertility.

Release Kinetics of Monomers from Dental Composites Containing Fluoride-Doped Calcium Phosphates.

This study analyse the type of release kinetic of specific monomers from dental resin composites containing various fluoride-doped calcium phosphates. The release behavior of urethane dimethacrylate (UDMA), ethoxylated bisphenol-A dimethacrylate (bis-EMA) and 1.6-hexanediol ethoxylate diacrylate (HEDA) was evaluated over a period of 35 days. Two tailored calcium phosphates doped with different concentrations of fluoride salts (VS10% and VS20%) were prepared and incorporated in the dimethacrylate matrix at various concentrations to generate a range of experimental composites. The release kinetics were characterized using mathematical models such as zero-order, first-order, Peppas and Higuchi models. The results showed that the first-order model best described the release kinetics. UDMA and HEDA exhibited significant differences in release compared to bis-EMA from day 1, while no significant differences were observed between UDMA and HEDA, except on day 35, when UDMA exhibited a higher release rate than HEDA. When comparing the release of each monomer, VS20-R20% had the highest total release percentage, with 3.10 ± 0.25%, whereas the composite VS10-R5% showed the lowest release percentage, with a total of 1.66 ± 0.08%. The release kinetics were influenced by the composition of the resin composites and the presence of calcium fluoride and sodium fluoride in the calcium phosphate played a role in the maximum amounts of monomer released. In conclusion, the release of monomers from the tested resin composites followed a first-order kinetic behaviour, with an initial rapid release that decreased over time. The composition of the resin monomers and the presence of fluoride salts influenced the release kinetics. The VS10-R5% and VS10-R10% resin composites exhibited the lowest total monomer release, suggesting its potential favourable composition with reduced monomer elution. These findings contribute to understanding the release behavior of dental resin composites and provide insights for the development of resin-based bioactive dental materials.

Effect of airborne particle abrasion treatment of two types of 3D-printing resin materials for permanent restoration materials on flexural strength.

This study aimed to assess the effects of airborne-particle abrasion (APA) on the flexural strength of two types of 3D-printing resins for permanent restoration. Two types of 3D printing resins (urethane dimethacrylate oligomer; UDMA, ethoxylated bisphenol-A dimethacrylate; BEMA) constituting different components were printed. The specimen surfaces were subjected to APA using 50 and 110µm alumina particles under different pressures. The three-point flexural strength was measured for each surface treatment group, and a Weibull analysis was performed. Surface characteristics were analyzed via surface roughness measurements and scanning electron microscopy. Dynamic mechanical analysis and nano-indentation measurements were limited to the control group. The three-point flexural strength according to the surface treatment was significantly lower in the UDMA group for large particle sizes and at high pressures; the BEMA group demonstrated low flexural strength for large particle sizes regardless of the pressure. After thermocycling, the flexural strengths of UDMA and BEMA significantly decreased in the group subjected to surface treatment. The Weibull modulus and characteristic strength of UDMA were higher than those of BEMA under different APA and thermocycling conditions. As the abrasion pressure and particle size increased, a porous surface formed, and the surface roughness increased. Compared with BEMA, UDMA featured a lower strain, greater strain recovery, and a negligible increase in modulus according to strain. Thus, surface roughness increased with the sandblasting particle size and pressure of the 3D-printing resin. Hence, a suitable surface treatment method to improve adhesion can be determined by considering physical property changes.

Effect of monomer composition and filler fraction on surface microhardness and depth of cure of experimental resin composites.

This study evaluated microhardness profiles and calculated depths of cure at 80% of the surface microhardness of experimental dental resin composites having different base monomer compositions and different filler fractions. Composites were prepared using four different base monomers (bisphenol A-glycidyl methacrylate [Bis-GMA], urethane dimethacrylate [UDMA], ethoxylated bisphenol-A dimethacrylate [Bis-EMA], and Fit-852) with triethylene glycol dimethacrylate (TEGDMA) used as a co-monomer at three filler:resin matrix weight percent fractions (50:50, 60:40, and 70:30). Uncured material was placed in 3D printed molds and light cured for 40 s from the top surface only. Knoop microhardness was measured at the top of the specimen, and at every 0.5mm up to 4mm in depth. Microhardness at the surface increased in all experimental composites as the filler fraction increased. When comparing base monomers, microhardness was the highest in UDMA-based composites, while Bis-GMA-based composites showed the lowest values. When comparing depth of cure as a function of base monomer type, both Bis-GMA and Bis-EMA showed significantly lower values than UDMA or Fit-852. Composites having 50wt% filler showed a significantly higher depth of cure than those with 60 and 70wt% filler. Base monomer and filler fraction significantly influence microhardness and depth of cure in these experimental composites.

Development of hesperetin methacrylates and their high performance thermosets

AbstractHesperetin based monomers substituted to varying degrees of methacrylate functionality were synthesized namely trimethacrylate, dimethacrylate and monomethacrylated hesperetin monomers, HTM, HDM and HMM respectively. Resins employing reactive diluents 4‐acryloylmorpholine (4AM) and styrene (Sty) were formulated. Resin formulations were determined to be Newtonian fluids with viscosities below 800 cP. Thermosets of hesperetin monomers were produced with glass transition temperature (Tg) values up to 225°C. Ultimate strength up to 20 MPa and tensile modulus of 5.0 GPa were also observed. Additionally, thermosets with char yield near 30% were measured. Char yield, ultimate strength and tensile modulus of hesperetin based thermosets were superior to those derived from the petrochemical bisphenol A dimethacrylate (BPAM). However, thermosets that employed hesperetin derived monomers displayed properties that were less than expected compared to Bicerano model predictions. Also, select HTM:Sty thermosets displayed a noticeable holographic type morphology. Reactivity ratios, spectroscopy, microscopy and structure property relationships indicated that poor copolymerization behavior during cure and high degrees of crosslinking during postcure were responsible for the microcrack formation in the material. This also caused the observed morphology and resulted in reduced properties relative to Bicerano predictions.

Effect of Adhesion Conditions on the Shear Bond Strength of 3D Printing Resins after Thermocycling Used for Definitive Prosthesis.

Three-dimensional (3D) printing polymers such as urethane dimethacrylate (UDMA) and ethoxylated bisphenol A dimethacrylate (Bis-EMA) are typically used in definitive prosthesis and require surface treatments before bonding. However, surface treatment and adhesion conditions often affect long-term use. Herein, polymers were divided into Groups 1 and 2 for the UDMA and Bis-EMA components, respectively. The shear bond strength (SBS) between two types of 3D printing resins and resin cements was measured using Rely X Ultimate Cement and Rely X U200, according to adhesion conditions such as single bond universal (SBU) and airborne-particle abrasion (APA) treatments. Thermocycling was performed to evaluate the long-term stability. Sample surface changes were observed using a scanning electron microscope and surface roughness measuring instrument. The effect of interaction between the resin material and adhesion conditions on the SBS was analyzed via a two-way analysis of variance. The optimal adhesion condition for Group 1 was achieved when U200 was used after APA and SBU, whereas Group 2 was not significantly affected by the adhesion conditions. After thermocycling, the SBS significantly decreased in Group 1 without APA treatment and in the entire Group 2. Additionally, porosity, along with increased roughness, was observed on both material surfaces after APA.

New Molecular Imprinting Nano Polymer Synthesis And Characterization As A Biocompatible For Drug Delivery Applications

New polymeric nanoparticles were to be developed for biomedical purposes as the purpose of this study. It was thought that theproduction of materials with novel properties and functions could be accomplished by meticulous design and synthesis, as well as theresearch of structure-property connections. A novel method that we developed has excellent sensitivity, cheap cost, and high stability.The molecularly imprinted polymer (MIP) used in this method, which is based on a functional monomer named polylactic acid(PLA), Acrylic acid (AA) , Methylacrylate (MA) Chitosan (Cs), Bisphenol A dimethacrylate(BADMA) , N,Ndimethylacrylamide(DMA), Polyvinylpyrrolidone (PVP), Ethylene glycol(EG), Methyl Methacrylate(MMA). To search into thepotential use of these hydrogels in controlled drug delivery systems, were crosslinked by 1,6 hexanedioldiacrylate (HDODA) andphotoinitiated by 1-hydroxycyclohexyl phenyl ketone before being polymerized using free radical polymerization.We synthesized the water-insoluble, amphiphilic polymer MIPs and for the first time described its structure and characteristics. Thispolymer, which has a nanostructure with a size of about 40-88 nm, is the ideal biocompatible polymer for nanobioapplications.Atenolol was loaded onto a produced hydrogel, and the drug release of such hydrogels in vitro and in vivo was studied. According tothe results, raising the pH accelerated the rate of drug release. Fourier transform infrared and 1HNMR spectroscopy, thermalgravimetric measurement, and scanning electron microscopy were used to analyze the produced hydrogels. I have been studyingabout the TGA and DSC utilizing argon medium gas and a 10 oC/min heating rate. The effect of TGA shows% residue between 2-12% at 500oC and char yield between 26- 50% at 400oC. Nanocopolymer hydrogels' glass transition values (Tg) ranged from 120 to275 °C.The faculty of biological science and biotechnology at Shahid Beheshti University also conducted studies on the efficiency of thesenanocopolymers using laboratory rats., Tehran, Iran on 18 Male Wistar rats weighing 200–240 g and divided rats into several groups,a group of natural control, and other groups for the induction of high pressure by Nacl (1%) and Dexamethasone, which includes ahigh pressure control group, , groups of treatment with polymers loaded with (Atenolol), and high pressure control groups, where Theresults showed that polymers have an obvious effect on lowering blood pressure levels in rats. Additionally, to avoid the issue ofincreased loading (Atenolol) caused by the treatment process (Atenolol), which is normally what happens as a result of an overdose,as well as to reduce the number of periodic blood pressure checks.

Influence of Alumina Nanoparticles on the Mechanical Properties of a Bioresin Composite

A significant part of the research and production activities is represented in the field of bioengineering by the biomaterials used in hard tissue restorations. They are of great interest in dental science, intending to improve technological aspects, monitoring their biological responses to the living organisms, but also to redesign economic aspects, beginning with the choice of raw materials. In the present work, light-curing composite biomaterials were made from a composite polymer matrix consisting of specific concentrations of bisphenol A-glycidyl methacrylate base monomer (Bis-GMA), a mixture of two co-monomers, triethylene glycol dimethacrylate and ethoxylated bisphenol A-dimethacrylate (TEGDMA/BisEMA), and two alumina nanopowder concentrations (5 wt.% and 10 wt.%). These materials were mechanically tested for flexural strength and compressive strength. The structural analysis of these materials consisted of SEM microscopy and EDX elementary mapping. In order to extract 3D projections of sample surfaces, but also to produce indicative values of their roughness, the SEM micrographs were processed with open-source software. In order to observe a clear evolution of the mentioned properties, the composite biomaterials were compared with materials formed only with the Bis-GMA/TEGDMA/BisEMA composite, and with a commercial composite resin, Filtek™ Supreme Ultra Universal Restorative, also. The findings showed an increase in the mechanical properties of the materials manufactured concerning the concentration of nanoparticles of aluminum. EDX analyzes confirmed the good homogeneity of nanoparticles in the polymer matrix. Mechanical properties of the manufactured nanocomposite biomaterials were reported 28.8 % higher than the control biomaterial. The comparison results with the commercial resin composite are encouraging.

An Evaluation of the Properties of Urethane Dimethacrylate-Based Dental Resins.

Most of the dental materials available on the market are still based on traditional monomers such as bisphenol A-glycidyl methacrylate (Bis-GMA), urethane dimethacrylate (UDMA), triethyleneglycol dimethacrylate (TEGDMA), and ethoxylated bisphenol-A dimethacrylate (Bis-EMA). The interactions that arise in the monomer mixture and the characteristics of the resulting polymer network are the most important factors, which define the final properties of dental materials. The use of three different monomers in proper proportions may create a strong polymer matrix. In this paper, fourteen resin materials, based on urethane dimethacrylate with different co-monomers such as Bis-GMA or Bis-EMA, were evaluated. TEGDMA was used as the diluting monomer. The flexural strength (FS), diametral tensile strength (DTS), and hardness (HV) were determined. The impacts of material composition on the water absorption and dissolution were evaluated as well. The highest FS was 89.5 MPa, while the lowest was 69.7 MPa. The median DTS for the tested materials was found to range from 20 to 30 MPa. The hardness of the tested materials ranged from 14 to 16 HV. UDMA/TEGDMA matrices were characterized by the highest adsorption values. The overall results indicated that changes in the materials’ properties are not strictly proportional to the material’s compositional changes. The matrices showed good properties when the composite contained an equal mixture of Bis-GMA/Bis-EMA and UDMA or the content of the UDMA monomer was higher.

Novel Crown Cement Containing Antibacterial Monomer and Calcium Phosphate Nanoparticles.

Oral biofilm accumulation at the tooth–restoration interface often leads to recurrent dental caries and restoration failure. The objectives of this study were to: (1) develop a novel bioactive crown cement containing dimethylaminohexadecyl methacrylate (DMAHDM) and nano-sized amorphous calcium phosphate (NACP), and (2) investigate the mechanical properties, anti-biofilm activity, and calcium (Ca2+) and phosphate (PO43−) ion release of the crown cement for the first time. The cement matrix consisted of pyromellitic glycerol dimethacrylate and ethoxylated bisphenol-A dimethacrylate monomers and was denoted PEHB resin matrix. The following cements were tested: (1) RelyX luting cement (commercial control); (2) 55% PEHB + 45% glass fillers (experimental control); (3) 55% PEHB + 20% glass + 25% NACP + 0% DMAHDM; (4) 52% PEHB + 20% glass + 25% NACP + 3% DMAHDM; (5) 51% PEHB + 20% glass + 25% NACP + 4% DMAHDM; (6) 50% PEHB + 20% glass + 25% NACP + 5% DMAHDM. Mechanical properties and ion release were measured. Streptococcus mutans (S. mutans) biofilms were grown on cements, and colony-forming units (CFUs) and other biofilm properties were measured. The novel bioactive cement demonstrated strong antibacterial properties and high levels of Ca2+ and PO43− ion release to remineralize tooth lesions. Adding NACP and DMAHDM into the cement did not adversely affect the mechanical properties and dentin bonding strength. In conclusion, the novel NACP + DMAHDM crown cement has excellent potential for restoration cementation to inhibit caries by suppressing oral biofilm growth and increasing remineralization via Ca2+ and PO43− ions. The NACP + DMAHDM composition may have wide applicability to other biomaterials to promote hard-tissue formation and combat bacterial infection.

Molecularly imprinted polymer thin-film as a micro-extraction adsorbent for selective determination of trace concentrations of polycyclic aromatic sulfur heterocycles in seawater

A tailor-made porous molecularly imprinted polymer (MIP) thin-film was prepared by in situ photo-radical polymerization on a glass slide and used as a microextraction adsorbent. Detection was carried out using gas chromatography-mass spectrometry (GC–MS) to afford a method suitable for the selective determination of trace concentrations of polycyclic aromatic sulfur heterocycles (PASHs) in seawater. PASHs are one of the most problematic aromatic organic pollutants, as they are considered more persistent and toxic compared to other analogous aromatic compounds in the environment. The optimized thin-film consisted of a 2-thiophenecarboxaldehyde pseudo-template with 1-vinylimidazole (1-Vim) as the functional monomer, bisphenol A dimethacrylate (BPADMA) as the cross-linker, acetonitrile as the porogen, and polyethylene glycol to boost porosity through formation of interpenetrating polymer networks. The adsorption behaviours of the thin-film, including adsorption kinetics, binding isotherms, and selectivity of MIP thin-film were investigated in detail. The highest imprinting factors (2.3–3.0) and adsorption capacity for targeted PASHs were achieved at a template:monomer:cross-linker ratio of 1:4:8. The method with no sample or film pretreatment showed very good reproducibility for the extraction of PASHs from spiked seawater samples (RSDs ≤ 6.0%, n = 3), was linear (R2 > 0.9960) over a range of 0.5–40 µg L−1, and gave limits of detection n the range of 0.029–0.166 µg L−1.

Degree of conversion of experimental resin composites containing bioactive glass 45S5: the effect of post-cure heating

Resin composites containing reinforcing inert glass fillers combined with bioactive glass (BG) can aid in the prevention of secondary caries, which is a major cause of failure of contemporary composite restorations. A series of previous studies on experimental resin composites filled with BG 45S5 has demonstrated that methacrylate resin polymerization can be impaired by the addition of unsilanized BG, leading to lower degrees of conversion (DC). In order to distinguish whether the polymerization inhibition is caused by a direct (temperature-independent) effect of BG or an indirect (temperature-dependent) effect of restricted mobility of reactive species, this study used Raman spectroscopy to evaluate the DC values of experimental composites post-cured at 37 °C and 150 °C. The potential of BG to adversely affect DC was highly dependent on the resin system. The highest DC reduction was observed in the resin system based on ethoxylated bisphenol A dimethacrylate (Bis-EMA), followed by bisphenol A glycidyl methacrylate (Bis-GMA). In contrast, the DC for urethane dimethacrylate (UDMA) was not compromised by BG. Increasing the mobility of reactive species by heating at 150 °C showed limited potential for increasing the DC in the Bis-EMA and Bis-GMA resin systems, indicating a direct inhibitory effect of BG on polymerization.

Mechanical properties, accuracy, and cytotoxicity of UV-polymerized 3D printing resins composed of Bis-EMA, UDMA, and TEGDMA

Statement of problemThree-dimensional printing has the potential for clinical applications, and additive manufacturing materials for dental use merit further investigation. PurposeThe purpose of this in vitro study was to evaluate the properties of materials formulated with ethoxylated bisphenol A-dimethacrylate (Bis-EMA), urethane dimethacrylate (UDMA), and triethylene glycol dimethacrylate (TEGDMA) as 3D printing resins for ultraviolet digital light processing (UV-DLP) 3D printers and to characterize the mechanical and biological properties and accuracy of the printed objects. Material and methodsTen different light-polymerized resins were formulated using Bis-EMA, UDMA, and TEGDMA. Their viscosities were measured, and only 7 resins with viscosities lower than 1500 centipoise (cP) were selected for 3D printing and further material characterization. The light-polymerized resins were printed into representative shapes using a custom-made 3D printer equipped with a 405-nm UV-DLP projector as the light source. The printed specimens were subjected to biologic, mechanical, and accuracy tests, and the data were submitted to 1-way ANOVA and Tukey post hoc comparisons (α=.05). ResultsPhotopolymerizable resins made of Bis-EMA, UDMA, and TEGDMA were successfully formulated for 3D printing to fabricate objects of various shapes and sizes. TEGDMA served as the diluent to reduce the viscosity and increase the degree of conversion, while UDMA and Bis-EMA provided strength as demonstrated by the mechanical testing. All the printed objects passed cytotoxicity testing. The flexural strengths of the printed specimens ranged between 60 MPa and 90 MPa; flexural modulus ranged between 1.7 GPa and 2.1 GPa; and surface hardness ranged between 14.5 HV and 24.6 HV. These represent similar mechanical properties to those of currently used clinical resin materials. In the accuracy test, the resin mixture composed of 80% Bis-EMA, 10% UDMA, and 10% TEGDMA had the highest accuracy, with a 0.051-mm deviation from the original design. ConclusionsBis-EMA, UDMA, and TEGDMA are good candidates for the formulation of 3D printing resins for dental use. The printed objects demonstrated favorable biological and mechanical properties. Further, the accuracy of the printed specimens showed potential for clinical application.

Modification of filler surface treatment of composite resins using alternative silanes and functional nanogels

ObjectivesThis study probes how modifiedapproaches for filler surface treatment in dental composites based on alternative silanes and functional nanogel additives affects physicochemical properties of these materials with a focus on polymerization stress development. MethodsNanogels were synthesized from isobornyl methacrylate, ethoxylated bisphenol-A dimethacrylate and isocyanatoethyl methacrylate followed by partial further reaction with 2-hydroxyethyl methacrylate to provide both isocyanate and methacrylate functionalization. A barium glass filler (˜1 μm particle size) was treated with either γ-methacryloxypropyltrimethoxysilane (MPS), N-methylaminopropyltrimethoxy (MAP) or N-allylaminopropyltrimethoxy (AAP) silanes. The reactive nanogels were then covalently attached to the aminosilane-treated fillers. Surface treatment was characterized by thermogravimetric analysis (TGA) and diffuse reflectance infrared spectroscopy (DR-IR). Composites were formulated with 60 wt% of the various functionalized fillers and the materials were evaluated for polymerization kinetics, polymerization stress (PS), volumetric shrinkage, mechanical properties and photorheology. Data were evaluated by one-way ANOVA and Tukey’s test at 5% significance level. ResultsFiller surface treatments were confirmed by TGA and DR-IR analyses. Nanogel-functionalized fillers significantly reduced PS up to 20%, while the degree of conversion and elastic modulus were not compromised. Similar storage modulus development during polymerization was observed among materials by photorheology although the rate of polymerization was significantly increased for nanogel-based treatments. A significant decrease in flexural strength was observed for amino functional silane groups; however, there was no statistical difference in strength for the MPS control group compared with the nanogel-modified composites. SignificanceFiller surface treatment modified with a reactive nanogel enables significant PS reduction, without compromise to degree of conversion or mechanical properties of dental composites.

Synthesis and characterization of molecularly hybrid bisphenols derived from lignin and CNSL: Application in thermosetting resins

Commercially available methacrylates often contain derivates of bisphenol A (BPA), a known human endocrine disruptor and petrochemical derived compound; therefore, alternatives are being investigated to increase sustainability and reduce toxicity. An asymmetric, bio-based bisphenol, VAC, was synthesized via an electrophilic aromatic condensation of vanillyl alcohol and cardanol. The alkyl side chain of VAC was subsequently hydrogenated to yield VAHC to determine the effects of side chain unsaturation on material properties. These bisphenols were methacrylated to prepare VACDM and VAHCDM, blended with a reactive diluent, cured, and compared to BPA dimethacrylate (BPADM), bio-based bisguaiacol dimethacrylate (BGDM), and a commercial BPA based vinyl ester (VE828). Resins containing VACDM and VAHCDM have reduced viscosities relative to BGDM and both BPA-based dimethacrylates, and the unsaturation on the side chain was shown to provide further reduced viscosities. Cured resins with VACDM and VAHCDM exhibit directly comparable thermal stability in both inert and oxidative environments, and decreased glass-transition temperatures due to increased aliphatic character relative to BPA-based resins. The toughness of the thermosets comprised of the bio-based bisphenols were greater than that of BPADM, where the alkyl substituent was shown to impart toughness into the network, yet the level of side chain saturation shows minimal effect on fracture toughness.

Protein-repelling adhesive resin containing calcium phosphate nanoparticles with repeated ion-recharge and re-releases

ObjectivesThe objectives were to develop a calcium (Ca) and phosphate (P) ion-rechargeable and protein-repellent adhesive containing nanoparticles of amorphous calcium phosphate (NACP) and 2-methacryloyloxyethyl phosphorylcholine (MPC), and investigate the MPC effects on ion recharge and re-releases for the first time. MethodsPyromellitic glycerol dimethacrylate and ethoxylated bisphenol-A dimethacrylate were used to fabricate adhesive PEHB. Six adhesives were tested: (1) Scotchbond (SBMP); (2) PEHB, (3) PEHB + 20%NACP; (4) PEHB + 30%NACP; (5) PEHB + 20%NACP+3%MPC; (6) PEHB + 30%NACP+3%MPC. Dentin shear bond strength, Ca/P ion release, recharge and re-release, and protein adsorption were measured. A microcosm biofilm model was tested for lactic-acid production and colony-forming units (CFU). ResultsAdding NACP + MPC did not negatively affect dentin bond strength (p > 0.1). With increasing the number of recharge/re-release cycles, the Ca/P ion re-release reached similarly higher levels (p > 0.1), indicating long-term remineralization capability. One recharge enabled the adhesives to have continued re-releases for 21 days. Incorporation of 3% MPC yielded 10-fold decrease in protein adsorption, and 1–2 log decrease in biofilm CFU. ConclusionsThe new rechargeable adhesive with MPC + 30%NACP greatly reduced protein adsorption, biofilm growth and lactic acid. Incorporation of MPC did not compromise the excellent Ca/P ion release, rechargeability, and dentin bond strength. Clinical significanceNovel bioactive adhesive containing MPC + NACP is promising to repel proteins and bacteria, and inhibit secondary caries at the restoration margins. The method of NACP + MPC to combine CaP-recharge and protein-repellency is applicable to the development of a new generation of materials including composites and cements to suppress oral biofilms and plaque formation and protect tooth structures.

Suppressing Thermally Induced Fullerene Aggregation in Organic Solar Cells by Employing Plastic Network

Thermally induced fullerene aggregation restricts the long-term stability in organic solar cells. Herein, we demonstrate an effective method of incorporating cross-linkable small-molecule ethoxylated (2) bisphenol-A dimethacrylate (BPA2EODMA) into poly(3-hexylthiophene-2,5-diyl):[6,6]-phenyl C61 butyric acid methyl ester (P3HT:PCBM) blends to form an insoluble framework and inhibit fullerene aggregation. The BPA2EODMA exhibits excellent heat and flexural endurance characteristics, which enhance the thermal and morphological stabilities of the active layer. By systematic research with time-resolved optical spectroscopy and microscopy, the morphological changes and charge-transfer dynamics in P3HT:PCBM blends are explored to unravel the underlying mechanisms for improved photovoltaic efficiency by incorporating the cross-linker. The power conversion efficiency (PCE) increased from 3.6 to 4.2% due to the BPA2EODMA incorporation into the active layer, which is ascribed to the enhancement of exciton dissociati...

Methacrylate based cross-linkers for improved thermomechanical properties and retention of radiation detection response in plastic scintillators

Pulse shape discrimination (PSD) is an important method that can efficiently sort and separate neutron and gamma radiation signals. PSD is currently achieved in plastic scintillators by over-doping poly(vinyl toluene) (PVT) matrices with fluorescent molecules. Meaningful separation of the signals requires addition of >20 wt% 2,5-diphenyloxazole (PPO) fluor in PVT. At these concentrations PPO acts as a plasticizer, negatively affecting the physical properties of the final plastic such as hardness, machinability, and thermomechanical stability. This work addresses these issues by implementing a cost-effective solution using cross-linking chemistry via commercially available bisphenol A dimethacrylate (BPA-DM), and a synthesized fluorinated analogue. Both improve the physical properties of over-doped PPO based plastic scintillators without degrading the measured light yield or PSD and Figure of Merit (FoM). In addition, the fluorinated analogue appears to enhance the hydrophobicity of the surface of the plastic scintillators, which may improve the scintillators’ resistance to water diffusion and subsequent radiation response degradation. The new formulations improve the feasibility of widely deploying long lifetime PSD capable plastic scintillators in large area coverage assemblies.

Influence of bioactive particles on the chemical-mechanical properties of experimental enamel resin infiltrants.

This study aimed at evaluating the chemophysical properties of experimental resin infiltrants (ERIs) doped with different bioactive particles. A control resin infiltrant (CR) was formulated using triethylene glycol dimethacrylate (TEGDMA) and ethoxylated bisphenol A dimethacrylate (BisEMA). Moreover, five experimental ERIs were also created by incorporating the following bioactive fillers (10wt%) into the CR: hydroxyapatite (Hap), amorphous calcium phosphate (ACP), zinc-polycarboxylated bioactive glass (BAG-Zn), bioactive glass 45S5 (BAG 45S5), and calcium silicate modified with beta tricalcium phosphate (β-TCP). ICON® resin infiltrant was also used as control. All the ERIs used in this study were assessed for degree of conversion (DC), Knoop microhardness (KHN), softening ratio (SR), tensile cohesive strength (TCS), modulus of elasticity (E-modulus), water sorption (WS), and solubility (SL). Data were subjected to ANOVA and Tukey's test (α=5%). ICON® presented the lowest DC, KHN, TCS, E-modulus, and SR. Incorporation of bioactive fillers into CR caused significant increase in the KHN. Conversely, no significant effect was observed on DC, TCS, and E-modulus. The resin infiltrant containing Hap showed a significant increase in softening ratio, while, ICON® presented the highest WS and SL. The WS of ACP-doped resin infiltrant was significantly higher than that of the Hap-doped infiltrant. The SL of the ACP-doped infiltrant was higher than CR BAG-Zn or BAG 45S5. The incorporation of bioactive particles into experimental resin infiltrants can improve the chemomechanical properties and reduce water sorption and solubility. Resin infiltrants doped with bioactive particles may improve the long-term performance of the treatment of white-spot lesions.