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1.
J Mater Sci Mater Med ; 32(10): 129, 2021 Oct 03.
Article in English | MEDLINE | ID: mdl-34601653

ABSTRACT

The current study focuses on the fabrication of calcium hydroxyapatite (Ca10(PO4)6(OH)2) (HA) in a nanorange having whiskers- and cubic-shaped uniform particle morphology. The synthesized HA particles hold a promising feature as reinforcement fillers in dental acrylic resin composite. They increase the efficacy of reinforcement by length and aspect ratio, uniformity, and monodispersity. Therefore, the acrylic resin was reinforced with the as-synthesized monodispersed HA filler particles (0.2-1 Wt%). The presence of filler particles in the composite had a noticeable effect on the tribological and mechanical properties of the dental material. The morphological effect of HA particles on these properties was also investigated, revealing that cubic-shaped particles showed better results than whiskers. The as-fabricated composite (0.4 Wt%) of the cubic-shaped filler particles showed maximum hardness and improved antiwear/antifriction properties. Particle loading played its part in determining the optimum condition, whereas particle size also influenced the reinforcement efficiency. The current study revealed that particle morphology, particle size, uniformity, etc., of HA fillers, greatly influenced the tribological and mechanical properties of the acrylic resin-based nanocomposite. Improvement in the tribological properties of HA particle-reinforced acrylic resin composites (HA-acrylic resin) followed the trend as AR < CmC < WC < CC.


Subject(s)
Dental Restoration, Permanent/instrumentation , Durapatite/pharmacology , Resins, Synthetic , Coated Materials, Biocompatible/chemical synthesis , Coated Materials, Biocompatible/chemistry , Composite Resins/chemical synthesis , Composite Resins/chemistry , Durapatite/chemistry , Hardness , Humans , Materials Testing , Microscopy, Electron, Scanning , Nanocomposites/chemistry , Nanoparticles/chemistry , Resins, Synthetic/chemical synthesis , Resins, Synthetic/chemistry , Resins, Synthetic/pharmacology , Surface Properties
2.
Int J Mol Sci ; 22(15)2021 07 28.
Article in English | MEDLINE | ID: mdl-34360861

ABSTRACT

In response to the demand for high-performance materials, epoxy thermosetting and its composites are widely used in various industries. However, their poor toughness, resulting from the high crosslinking density of the epoxy network, must be improved to expand their application to the manufacturing of flexible products. In this study, ductile epoxy thermosetting was produced using thiol compounds with functionalities of 2 and 3 as curing agents. The mechanical properties of the epoxy were further enhanced by incorporating fumed silica into it. To increase the filler dispersion, epoxide-terminated polydimethylsiloxane was synthesized and used as a composite component. Thanks to the polysiloxane-silica interaction, the nanosilica was uniformly dispersed in the epoxy composites, and their mechanical properties improved with increasing fumed silica content up to 5 phr (parts per hundred parts of epoxy resin). The toughness and impact strength of the composite containing 5 phr nanosilica were 5.17 (±0.13) MJ/m3 and 69.8 (±1.3) KJ/m2, respectively.


Subject(s)
Composite Resins/chemical synthesis , Epoxy Resins/chemical synthesis , Dimethylpolysiloxanes/chemistry , Materials Testing , Silicon Dioxide/chemistry , Surface Properties , Tensile Strength
3.
Int J Mol Sci ; 22(7)2021 Apr 03.
Article in English | MEDLINE | ID: mdl-33916847

ABSTRACT

Rigid polyurethane (PUR) foams reinforced with 1, 2, and 5 wt.% of salvia filler (SO filler) and montmorillonite-modified salvia filler (MMT-modified SO filler) were produced in the following study. The impact of 1, 2, and 5 wt.% of SO filler and MMT-modified SO filler on the morphological, chemical, and mechanical properties of PUR composites were examined. In both cases, the addition of 1 and 2 wt.% of SO fillers resulted in the synthesis of PUR composites with improved physicomechanical properties, while the addition of 5 wt.% of SO fillers resulted in the formation of PUR composites with a less uniform structure and, therefore, some deterioration in their physicomechanical performances. Moreover, the results showed that the modification of SO filler with MMT improved the interphase compatibility between filler surface and PUR matrix. Therefore, such reinforced PUR composites were characterized by a well-developed closed-cell structure and improved mechanical, thermal, and flame-retardant performances. For example, when compared with reference foam, the addition of 2 wt.% of MMT-modified SO filler resulted in the formation of PUR composites with greater mechanical properties (compressive strength, flexural strength) and improved dynamic-mechanical properties (storage modulus). The PUR composites were characterized by better thermal stability as well as improved flame retardancy-e.g., decreased peak rate of heat release (pHRR), reduced total smoke release (TSR), and increased limiting oxygen index (LOI).


Subject(s)
Bentonite/chemistry , Composite Resins , Polyurethanes/chemistry , Salvia officinalis/chemistry , Composite Resins/chemical synthesis , Composite Resins/chemistry
4.
Int J Mol Sci ; 22(16)2021 Aug 17.
Article in English | MEDLINE | ID: mdl-34445545

ABSTRACT

Six novel urethane-dimethacrylate analogues (QAUDMAs) were synthesized and characterized. They consisted of the 2,4,4,-trimethylhexamethylene diisocyanate (TMDI) core and two methacrylate-terminated wings containing quaternary ammonium groups substituted with alkyl chains of 8, 10, 12, 14, 16, or 18 carbon atoms. QAUDMAs, due to the presence of quaternary ammonium groups, may have possible antibacterial effects. Since they showed satisfactory physicochemical properties, they will be subjected to further research towards the development of dental composites with a capacity to reduce secondary caries. The synthesis of QAUDMAs included three stages: (i) transesterification of methyl methacrylate (MMA) with N-methyldiethanolamine (MDEA), (ii) N-alkylation of the tertiary amino group with alkyl bromide, and (iii) addition of TMDI to the intermediate achieved in the second stage. The formation of QAUDMAs was confirmed by 1H and 13C NMR. They were characterized for density (dm), viscosity (η), refractive index (RI), glass transition temperature (Tg), polymerization shrinkage (S), and degree of conversion (DC). QAUDMAs were yellow, viscous resins (the η values ranged from 1.28 × 103 to 1.39 × 104 Pa·s, at 50 °C). Their RI ranged from 1.50 to 1.52, Tg from -31 to -15 °C, DC from 53 to 78%, and S from 1.24 to 2.99%, which is appropriate for dental applications.


Subject(s)
Ammonium Compounds/chemistry , Composite Resins/chemical synthesis , Methacrylates/chemistry , Polyurethanes/chemistry , Materials Testing , Pilot Projects , Polymerization , Surface Properties , Viscosity
5.
Clin Oral Investig ; 23(2): 965-974, 2019 Feb.
Article in English | MEDLINE | ID: mdl-29911287

ABSTRACT

OBJECTIVES: To evaluate the antibacterial activity, bacterial viability, cytotoxicity, and mechanical/physical properties of a novel methacrylate triclosan-derivative monomer (TM) incorporated in dental resin composite. METHODS: TM was synthesized by esterification and, after characterization by FT-IR, was added to an experimental composite. Samples were divided into two groups according to TM presence, i.e., C1 (control) and C2 (C1 + 14.4% TM). Microbiological properties: Specimens (C1 and C2) were prepared and placed on bacterial suspensions of Streptococcus mutans. Antibacterial activity, MTT, and live/dead bacterial viability were used to test the resin composites. All assays were performed in triplicates. Mechanical properties: Specimens underwent compression (CS) and flexural strength (FS) tests conducted in an Instron universal testing machine at a crosshead speed of 0.5 mm/min. Physical properties: Specimens were assessed for Knoop hardness (KHN) and crosslink density (CD). Fourier transform infrared spectroscopy allowed the degree of conversion (DC) to be evaluated. Data were subjected to appropriate statistical tests according to data distribution and assay (p < 0.05). RESULTS: Microbiological properties: C2 showed the lowest biofilm accumulation and the highest membrane-compromised bacteria in the biofilm. Mechanical/physical properties: For CS, FS, KHN, and DC, there was no significant difference between groups C1 and C2; however, significant difference was observed for the CD assay. CONCLUSIONS: The triclosan methacrylate reduces bacterial adhesion of S. mutans and decreased the formation of bacterial biofilm without affecting important polymer properties. The triclosan methacrylate incorporated in resin composite could greatly reduce the live bacterial adhesion of S. mutans and decrease the formation of bacterial biofilm without affecting important polymer properties. CLINICAL SIGNIFICANCE: The resin composites containing triclosan methacrylate could greatly reduce the bacterial adhesion and biofilm formation. That might prevent the secondary caries round the margins of the restorations.


Subject(s)
Acrylic Resins/chemical synthesis , Anti-Bacterial Agents/chemistry , Bacterial Adhesion/drug effects , Biofilms/drug effects , Composite Resins/chemical synthesis , Methacrylates/chemistry , Polyurethanes/chemical synthesis , Triclosan/chemistry , Compressive Strength , Flexural Strength , Hardness , Materials Testing , Spectroscopy, Fourier Transform Infrared , Streptococcus mutans/drug effects
6.
Int J Mol Sci ; 20(23)2019 Nov 30.
Article in English | MEDLINE | ID: mdl-31801235

ABSTRACT

Fiber-reinforced composite (FRC) retainers are an aesthetic alternative to conventional Stainless Steel splints. They are generally used with a full bonded technique, but some studies demonstrated that they could be managed with a spot bonding technique to significantly decrease their rigidity. In order to propose this FRC spot bonding technique for clinical use, the aim of this study was to evaluate mechanical properties and surface wear of fibers left uncovered. Tests were made by simulating tooth brushing, comparing FRC spot bonding technique splints with stainless steel and FRC traditional technique splints. Specimens were tested both at 0.1 mm of deflection and at maximum load, showing higher values of rigidity for the FRC full bonded technique. After tooth brushing, no significant reduction in values at 0.1 mm deflection was reported, while we found a similar reduction in these values for the Stainless Steel and FRC spot bonding technique at maximum load, and no significant variation for the FRC full bonded technique. SEM images after tooth brushing showed wear for FRC fibers left uncovered, while no relevant wear signs in metal and conventional FRC fibers were noticed. Results showed that FRC spot bonding technique has advantages in mechanical properties when compared to the FRC traditional full bonding technique, also after tooth brushing. However, the surface wear after tooth brushing in the FRC spot bonding technique is considerable and other tests must be performed before promoting this technique for routine clinical use.


Subject(s)
Composite Resins/analysis , Dental Materials/analysis , Mineral Fibers/analysis , Stainless Steel/analysis , Composite Resins/chemical synthesis , Dental Bonding/methods , Dental Materials/chemistry , Humans , Materials Testing/methods , Stress, Mechanical , Surface Properties
7.
Int J Mol Sci ; 17(12)2016 Dec 01.
Article in English | MEDLINE | ID: mdl-27916947

ABSTRACT

With the aim of reducing human exposure to Bisphenol A (BPA) derivatives in dentistry, a fluorinated dimethacrylate monomer was synthesized to replace 2,2-bis[4-(2-hydroxy-3-methacryloy-loxypropyl)-phenyl]propane (Bis-GMA) as the base monomer of dental resin. After mixing with reactive diluent triethyleneglycol dimethacrylate (TEGDMA), fluorinated dimethacrylate (FDMA)/TEGDMA was prepared and compared with Bis-GMA/TEGDMA in physicochemical properties, such as double bond conversion (DC), volumetric shrinkage (VS), water sorption (WS) and solubility (WSL), flexural strength (FS) and modulus (FM). The results showed that, when compared with Bis-GMA based resin, FDMA-based resin had several advantages, such as higher DC, lower VS, lower WS, and higher FS after water immersion. All of these revealed that FDMA had potential to be used as a substitute for Bis-GMA. Of course, many more studies, such as biocompatibility testing, should be undertaken to prove whether FDMA could be applied in clinic.


Subject(s)
Biocompatible Materials/chemistry , Dental Materials/chemistry , Polyethylene Glycols/chemistry , Polymethacrylic Acids/chemistry , Resins, Synthetic/chemistry , Benzhydryl Compounds/chemistry , Benzhydryl Compounds/therapeutic use , Biocompatible Materials/chemical synthesis , Biocompatible Materials/therapeutic use , Composite Resins/chemical synthesis , Composite Resins/chemistry , Dental Materials/chemical synthesis , Dental Materials/therapeutic use , Halogenation , Humans , Phenols/chemistry , Phenols/therapeutic use , Polyethylene Glycols/chemical synthesis , Polymethacrylic Acids/chemical synthesis , Resins, Synthetic/chemical synthesis , Resins, Synthetic/therapeutic use , Solubility , Water/chemistry
8.
Molecules ; 21(3): 292, 2016 Feb 29.
Article in English | MEDLINE | ID: mdl-26938511

ABSTRACT

Polyacrylic acid (PAA) is an important industrial chemical, which has been extensively applied in various fields, including for several biomedical purposes. In this study, we report the synthesis and modification of this polymer with various phenol imides, such as succinimide, phthalimide and 1,8-naphthalimide. The as-synthesized derivatives were used to prepare polymer metal composites by the reaction with Zn(+2). These composites were characterized by using various techniques, including NMR, FT-IR, TGA, SEM and DSC. The as-prepared PAA-based composites were further evaluated for their anti-microbial properties against various pathogens, which include both Gram-positive and Gram-negative bacteria and different fungal strains. The synthesized composites have displayed considerable biocidal properties, ranging from mild to moderate activities against different strains tested.


Subject(s)
Acrylic Resins/chemical synthesis , Acrylic Resins/pharmacology , Anti-Infective Agents/chemical synthesis , Anti-Infective Agents/pharmacology , Zinc/chemistry , Acrylic Resins/chemistry , Anti-Infective Agents/chemistry , Composite Resins/chemical synthesis , Composite Resins/chemistry , Composite Resins/pharmacology , Fungi/drug effects , Gram-Negative Bacteria/drug effects , Gram-Positive Bacteria/drug effects , Magnetic Resonance Imaging , Microbial Sensitivity Tests , Molecular Structure
9.
Biomacromolecules ; 16(8): 2265-75, 2015 Aug 10.
Article in English | MEDLINE | ID: mdl-26176305

ABSTRACT

This study reports a synthetic polymer functionalized with catechol groups as dental adhesives. We hypothesize that a catechol-functionalized polymer functions as a dental adhesive for wet dentin surfaces, potentially eliminating the complications associated with saliva contamination. We prepared a random copolymer containing catechol and methoxyethyl groups in the side chains. The mechanical and adhesive properties of the polymer to dentin surface in the presence of water and salivary components were determined. It was found that the new polymer combined with an Fe(3+) additive improved bond strength of a commercial dental adhesive to artificial saliva contaminated dentin surface as compared to a control sample without the polymer. Histological analysis of the bonding structures showed no leakage pattern, probably due to the formation of Fe-catechol complexes, which reinforce the bonding structures. Cytotoxicity test showed that the polymers did not inhibit human gingival fibroblast cells proliferation. Results from this study suggest a potential to reduce failure of dental restorations due to saliva contamination using catechol-functionalized polymers as dental adhesives.


Subject(s)
Catechols/chemistry , Dental Cements/chemistry , Methacrylates/chemistry , Polymers/chemistry , Catechols/chemical synthesis , Composite Resins/chemical synthesis , Composite Resins/chemistry , Dental Bonding , Dental Cements/chemical synthesis , Dentin/chemistry , Humans , Materials Testing , Polymers/chemical synthesis , Surface Properties , Tensile Strength
10.
Biomacromolecules ; 16(4): 1442-7, 2015 Apr 13.
Article in English | MEDLINE | ID: mdl-25738936

ABSTRACT

N-bromo-dimethylhydantoin polystyrene beads were synthesized and tested as antimicrobial agents for water microbial decontamination. Optimization of synthetic process was thoroughly investigated, including solvents used, ratio of reactants and reaction conditions, kilogram scale production, and detailed spectral analysis. The microbial inactivation efficiency was studied according to the NSF-231 Guide Standard and Protocol for Testing Microbiological Water Purifiers against Escherichia coli and MS2 phage. The tested resins maintained their activity for 550 L. Thus, N-bromo-dimethylhydantoin-polystyrene beads synthesized under optimized conditions at kilogram quantities have a potential use in water purification filters.


Subject(s)
Anti-Infective Agents/chemistry , Bromine/chemistry , Composite Resins/chemistry , Hydantoins/chemistry , Polystyrenes/chemistry , Water Purification/methods , Anti-Infective Agents/chemical synthesis , Anti-Infective Agents/pharmacology , Composite Resins/chemical synthesis , Composite Resins/pharmacology , Escherichia coli/drug effects
11.
Cell Mol Biol (Noisy-le-grand) ; 61(5): 52-7, 2015 Oct 16.
Article in English | MEDLINE | ID: mdl-26475389

ABSTRACT

A novel biocompatible resin monomer 4—3—(acryloyloxy)—2—hydroxypropoxy) phenyl 4—(3—(acryloyloxy)—2—hydroxypropoxy) benzoate, as an oral restorative — acrylate liquid crystalline resin monomer (ALCRM) was synthesized. The intermediate product and the final product were characterized by differential scanning calorimetry (DSC), polarized optical microscope (POM), and nuclear magnetic resonance (NMR). A resin matrix which has a potential application in dental composites was prepared by photopolymerizing ALCRM and triethylene glycol dimethacrylate (TEGDMA) as a primary and diluted monomer with a photosensitizer of camphorquinone (CQ) and 2—(Dimethylamino)ethyl methacrylate (DMAEMA) mixture. The molar ratio of ALCRM and TEGDMA was 7:3. The properties such as the curing depth, curing time, and the volumetric shrinkage of the resin matrix were investigated and compared with a traditional composite resin matrix Bis—GMA. After photocuring polymerization, the conversion degree of the resin matrix is 68.06%, higher than Bis—GMA/TEGDMA; the curing time is 4.08±0.20min, the curing depth is 2.10±0.17mm, and the volumetric shrinkage is 3.62%±0.26%. All the properties exhibit a better performance of the prepared resin matrix than Bis—GMA.


Subject(s)
Acrylates/chemical synthesis , Benzoates/chemical synthesis , Composite Resins/chemical synthesis , Dental Restoration Repair/methods , Acrylates/chemistry , Benzoates/chemistry , Calorimetry, Differential Scanning , Camphor/analogs & derivatives , Camphor/chemistry , Composite Resins/chemistry , Magnetic Resonance Spectroscopy , Methacrylates/chemistry , Microscopy, Polarization , Polyethylene Glycols/chemistry , Polymethacrylic Acids/chemistry
12.
Lasers Med Sci ; 30(5): 1497-503, 2015 Jul.
Article in English | MEDLINE | ID: mdl-25895056

ABSTRACT

The selection of a light-curing unit for the curing composite resins is important to achieve best outcomes. The purpose of the present study was to test lasers of 457 and 473 nm alone or in combination under different light conditions with respect to the cure of composite resins. Four different composite resins were light cured using five different laser combinations (530 mW/cm(2) 457 nm only, 530 mW/cm(2) 473 nm only, 177 mW/cm(2) 457 + 177 mW/cm(2) 473 nm, 265 mW/cm(2) 457 + 265 mW/cm(2) 473 nm, and 354 mW/cm(2) 457 + 354 mW/cm(2) 473 nm). Microhardness and polymerization shrinkage were evaluated. A light-emitting diode (LED) unit was used for comparison purposes. On top surfaces, after aging for 24 h, microhardness achieved using the LED unit and the lasers with different conditions ranged 42.4-65.5 and 38.9-67.7 Hv, respectively, and on bottom surfaces, corresponding ranges were 25.2-56.1 and 18.5-55.7 Hv, respectively. Of the conditions used, 354 mW/cm(2) 457 nm + 354 mW/cm(2) 473 nm produced the highest bottom microhardness (33.8-55.6 Hv). On top and bottom surfaces, microhardness by the lowest total light intensity, 354 (177 × 2) mW/cm(2), ranged 39.0-60.5 and 18.5-52.8 Hv, respectively. Generally, 530 mW/cm(2) at 457 nm produced the lowest polymerization shrinkage. However, shrinkage values obtained using all five laser conditions were similar. The study shows the lasers of 457 and 473 nm are useful for curing composite resins alone or in combination at much lower light intensities than the LED unit.


Subject(s)
Composite Resins/chemical synthesis , Curing Lights, Dental , Lasers, Semiconductor , Bisphenol A-Glycidyl Methacrylate/chemistry , Hardness , Materials Testing , Polymerization
13.
J Mater Sci Mater Med ; 25(4): 1183-94, 2014 Apr.
Article in English | MEDLINE | ID: mdl-24435527

ABSTRACT

The aim of this study was to prepare urethane dimethacrylates containing quaternary alkyl (C16, C12) ammonium and polyethylene glycol short sequences (Mn, 400 g/mol) and to investigate their behaviour in some experimental formulations in order to evaluate their potential applicability in the dental composites field. The structure of urethane dimethacrylates has been confirmed by (1)H ((13)C) NMR and FTIR spectra, as well as by electrospray ionization tandem mass spectroscopy, and gel permeation chromatography measurements. The effects of the cationic macromers on the properties of the filled/non-filled composites were examined through FTIR, photoDSC, and specific measurements as volumetric polymerization shrinkage, water sorption/solubility, contact angle, mechanical parameters, and morphology. The monomer compositions based on cationic dimethacrylate (6.88-27.52 wt%), BisGMA-analogue (48.18-68.82 wt%) and TEGDMA (23.3 wt%) showed a good photoreactivity in terms of double bond conversion (DC, 50.07-68.81 %) and polymerization rate (Rp, 0.099-0.141 s(-1)) measured by photoDSC compared to a control sample (BisGMA-1/TEGDMA: DC, 45.91 %; Rp, 0.162 s(-1)), while the polymerization shrinkage increased in acceptable limits (5.37-7.74 vol%). The mechanical properties (compressive, flexural and diametral tensile strength) of the composite resin incorporating 70 wt% silanized zirconium silicate micro/nanopowder can be modulated by the initial co-monomer concentrations.


Subject(s)
Composite Resins/chemistry , Methacrylates/chemistry , Polyurethanes/chemistry , Composite Resins/chemical synthesis , Magnetic Resonance Spectroscopy , Materials Testing , Mechanical Phenomena , Microscopy, Electron, Scanning , Molecular Structure , Photochemical Processes , Polymethacrylic Acids/chemistry , Quaternary Ammonium Compounds/chemistry , Solubility , Surface Properties
14.
J Formos Med Assoc ; 113(4): 242-8, 2014 Apr.
Article in English | MEDLINE | ID: mdl-24685300

ABSTRACT

BACKGROUND/PURPOSE: Polymerization shrinkage is one of the main causes of dental restoration failure. This study tried to conjugate two diisocyanate side chains to dimethacrylate resins in order to reduce polymerization shrinkage and increase the hardness of composite resins. METHODS: Diisocyanate, 2-hydroxyethyl methacrylate, and bisphenol A dimethacrylate were reacted in different ratios to form urethane-modified new resin matrices, and then mixed with 50 wt.% silica fillers. The viscosities of matrices, polymerization shrinkage, surface hardness, and degrees of conversion of experimental composite resins were then evaluated and compared with a non-modified control group. RESULTS: The viscosities of resin matrices increased with increasing diisocyanate side chain density. Polymerization shrinkage and degree of conversion, however, decreased with increasing diisocyanate side chain density. The surface hardness of all diisocyanate-modified groups was equal to or significantly higher than that of the control group. CONCLUSION: Conjugation of diisocyanate side chains to dimethacrylate represents an effective means of reducing polymerization shrinkage and increasing the surface hardness of dental composite resins.


Subject(s)
Acrylic Resins/chemical synthesis , Composite Resins/chemical synthesis , Isocyanates/chemistry , Methacrylates/chemistry , Polyurethanes/chemical synthesis , Acrylic Resins/chemistry , Composite Resins/chemistry , Hardness , Polymerization , Polyurethanes/chemistry
15.
Dent Mater ; 40(6): 941-950, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38719709

ABSTRACT

OBJECTIVE: Bisphenol A glycidyl methacrylate (Bis-GMA) is of great importance for dental materials as the preferred monomer. However, the presence of bisphenol-A (BPA) core in Bis-GMA structure causes potential concerns since it is associated with endocrine diseases, developmental abnormalities, and cancer lesions. Therefore, it is desirable to develop an alternative replacement for Bis-GMA and explore the intrinsic relationship between monomer structure and resin properties. METHODS: Here, the betulin maleic diester derivative (MABet) was synthesized by a facile esterification reaction using plant-derived betulin and maleic anhydride as raw materials. Its chemical structure was confirmed by 1H and 13C NMR spectra, FT-IR spectra, and HR-MS, respectively. The as-synthesized MABet was then used as polymerizable comonomer to partially or completely substitute Bis-GMA in a 50:50 Bis-GMA: TEGDMA resin (5B5T) to formulate dental restorative resins. These were then determined for the viscosity behavior, light transmittance, real-time degree of conversion, residual monomers, mechanical performance, cytotoxicity, and antibacterial activity against Streptococcus mutans (S. mutans) in detail. RESULTS: Among all experimental resins, increasing the MABet concentration to 50 wt% made the resultant 5MABet5T resin have a maximum in viscosity and appear dark yellowish after polymerization. In contrast, the 1MABet4B5T resin with 10 wt% MABet possessed comparable shear viscosity and polymerization conversion (46.6 ± 1.0% in 60 s), higher flexural and compressive strength (89.7 ± 7.8 MPa; 345.5 ± 14.4 MPa) to those of the 5B5T control (48.5 ± 0.6%; 65.7 ± 6.7 MPa; 223.8 ± 57.1 MPa). This optimal resin also had significantly lower S. mutans colony counts (0.35 ×108 CFU/mL) than 5B5T (7.6 ×108 CFU/mL) without affecting cytocompatibility. SIGNIFICANCE: Introducing plant-derived polymerizable MABet monomer into dental restorative resins is an effective strategy for producing antibacterial dental materials with superior physicochemical property.


Subject(s)
Anti-Bacterial Agents , Bisphenol A-Glycidyl Methacrylate , Materials Testing , Streptococcus mutans , Triterpenes , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/chemical synthesis , Triterpenes/chemistry , Triterpenes/pharmacology , Streptococcus mutans/drug effects , Bisphenol A-Glycidyl Methacrylate/chemistry , Viscosity , Dental Materials/chemistry , Dental Materials/pharmacology , Dental Materials/chemical synthesis , Polymerization , Polymethacrylic Acids/chemistry , Polymethacrylic Acids/pharmacology , Composite Resins/chemistry , Composite Resins/chemical synthesis , Composite Resins/pharmacology , Polyethylene Glycols/chemistry , Spectroscopy, Fourier Transform Infrared , Betulinic Acid
16.
Biomacromolecules ; 14(3): 771-80, 2013 Mar 11.
Article in English | MEDLINE | ID: mdl-23323677

ABSTRACT

A series of renewable bis(cyanate) esters have been prepared from bisphenols synthesized by condensation of 2-methoxy-4-methylphenol (creosol) with formaldehyde, acetaldehyde, and propionaldehyde. The cyanate esters have been fully characterized by infrared spectroscopy, (1)H and (13)C NMR spectroscopy, and single crystal X-ray diffraction. These compounds melt from 88 to 143 °C, while cured resins have glass transition temperatures from 219 to 248 °C, water uptake (96 h, 85 °C immersion) in the range of 2.05-3.21%, and wet glass transition temperatures from 174 to 193 °C. These properties suggest that creosol-derived cyanate esters may be useful for a wide variety of military and commercial applications. The cure chemistry of the cyanate esters has been studied with FTIR spectroscopy and differential scanning calorimetry. The results show that cyanate esters with more sterically demanding bridging groups cure more slowly, but also more completely than those with a bridging methylene group. In addition to the structural differences, the purity of the cyanate esters has a significant effect on both the cure chemistry and final Tg of the materials. In some cases, post-cure of the resins at 350 °C resulted in significant decomposition and off-gassing, but cure protocols that terminated at 250-300 °C generated void-free resin pucks without degradation. Thermogravimetric analysis revealed that cured resins were stable up to 400 °C and then rapidly degraded. TGA/FTIR and mass spectrometry results showed that the resins decomposed to phenols, isocyanic acid, and secondary decomposition products, including CO2. Char yields of cured resins under N2 ranged from 27 to 35%, while char yields in air ranged from 8 to 11%. These data suggest that resins of this type may potentially be recycled to parent phenols, creosol, and other alkylated creosols by pyrolysis in the presence of excess water vapor. The ability to synthesize these high temperature resins from a phenol (creosol) that can be derived from lignin, coupled with the potential to recycle the composites, provides a possible route to the production of sustainable, high-performance, thermosetting resins with reduced environmental impact.


Subject(s)
Composite Resins/chemical synthesis , Cresols/chemistry , Cyanates/chemical synthesis , Esters/chemical synthesis , Acetaldehyde/chemistry , Benzhydryl Compounds/chemistry , Calorimetry, Differential Scanning , Hot Temperature , Lignin/chemistry , Magnetic Resonance Spectroscopy , Phenols/chemistry , Spectroscopy, Fourier Transform Infrared , Thermogravimetry , Transition Temperature , X-Ray Diffraction
17.
J Mater Sci Mater Med ; 24(5): 1145-52, 2013 May.
Article in English | MEDLINE | ID: mdl-23440429

ABSTRACT

The purpose of this study was to investigate the effect of fiber orientation of a fiber-reinforced composite (FRC) made of poly-methyl-methacrylate (PMMA) and E-glass to the surface fabrication process by solvent dissolution. Intention of the dissolution process was to expose the fibers and create a macroporous surface onto the FRC to enhance bone bonding of the material. The effect of dissolution and fiber direction to the bone bonding capability of the FRC material was also tested. Three groups of FRC specimens (n = 18/group) were made of PMMA and E-glass fiber reinforcement: (a) group with continuous fibers parallel to the surface of the specimen, (b) continuous fibers oriented perpendicularly to the surface, (c) randomly oriented short (discontinuous) fibers. Fourth specimen group (n = 18) made of plain PMMA served as controls. The specimens were subjected to a solvent treatment by tetrahydrofuran (THF) of either 5, 15 or 30 min of time (n = 6/time point), and the advancement of the dissolution (front) was measured. The solvent treatment also exposed the fibers and created a surface roughness on to the specimens. The solvent treated specimens were embedded into plaster of Paris to simulate bone bonding by mechanical locking and a pull-out test was undertaken to determine the strength of the attachment. All the FRC specimens dissolved as function of time, as the control group showed no marked dissolution during the study period. The specimens with fibers along the direction of long axis of specimen began to dissolve significantly faster than specimens in other groups, but the test specimens with randomly oriented short fibers showed the greatest depth of dissolution after 30 min. The pull-out test showed that the PMMA specimens with fibers were retained better by the plaster of Paris than specimens without fibers. However, direction of the fibers considerably influenced the force of attachment. The fiber reinforcement increases significantly the dissolution speed, and the orientation of the glass fibers has great effect on the dissolving depth of the polymer matrix of the composite, and thus on the exposure of fibers. The glass fibers exposed by the solvent treatment enhanced effectively the attachment of the specimen to the bone modeling material.


Subject(s)
Bone Substitutes/chemistry , Coated Materials, Biocompatible/chemical synthesis , Composite Resins/chemical synthesis , Glass/chemistry , Polymethyl Methacrylate/chemistry , Bone Substitutes/chemical synthesis , Coated Materials, Biocompatible/chemistry , Composite Resins/chemistry , Materials Testing/instrumentation , Materials Testing/methods , Microscopy, Electron, Scanning , Polymers/chemical synthesis , Polymers/chemistry , Polymethyl Methacrylate/chemical synthesis , Stress, Mechanical , Surface Properties , Tensile Strength/physiology
18.
J Mater Sci Mater Med ; 23(5): 1149-55, 2012 May.
Article in English | MEDLINE | ID: mdl-22407000

ABSTRACT

The aim of this work was to synthesize and investigate properties of a novel dimethacrylic monomer based on bioderived alicyclic diol--isosorbide. Its potential as a possible substitute of 2,2-bis[4-(2-hydroxy-3-methacryloyloxypropoxy)phenyl]propane (BISGMA), widely used in dental restorative materials and suspected for toxicity was assessed. The novel monomer was obtained in a three-step synthesis. First, isosorbide was etherified by a Williamson nucleophilic substitution and subsequently oxidized to isosorbide diglycidyl ether (ISDGE). A triphenyl phosphine catalyzed addition of methacrylic acid to ISDGE resulted in 2,5-bis(2-hydroxy-3-methacryloyloxypropoxy)- 1,4:3,6-dianhydro-sorbitol (ISDGMA). The monomer obtained was photopolymerized using camphorquinone/2-(dimethylamino)ethyl methacrylate initiating system. Next, compositions with triethylene glycol dimethacrylate (TEGDMA) were prepared and polymerized. Double bond conversion, polymerization shrinkage and water sorption of resulting polymers were determined. Selected mechanical (flexular strength and modulus, Brinell hardness) and thermomechanical (DMA analysis) properties were also investigated. BISGMA based materials were prepared as reference for comparison of particular properties.


Subject(s)
Bisphenol A-Glycidyl Methacrylate/chemistry , Dental Materials/chemistry , Dental Materials/chemical synthesis , Isosorbide/analogs & derivatives , Adsorption , Biomechanical Phenomena , Bisphenol A-Glycidyl Methacrylate/chemical synthesis , Composite Resins/chemical synthesis , Composite Resins/chemistry , Elastic Modulus , Hardness/physiology , Isosorbide/chemical synthesis , Isosorbide/chemistry , Materials Testing , Models, Biological , Polymerization , Specific Gravity , Water/metabolism , Wettability
19.
J Mater Sci Mater Med ; 23(6): 1553-61, 2012 Jun.
Article in English | MEDLINE | ID: mdl-22466818

ABSTRACT

A novel furanone-containing antibacterial resin composite has been prepared and evaluated. compressive strength (CS) and Streptococcus mutans viability were used to evaluate the mechanical strength and antibacterial activity of the composites. The modified resin composites showed a significant antibacterial activity without substantially decreasing the mechanical strengths. With 5-30 % addition of the furanone derivative, the composite kept its original CS unchanged but showed a significant antibacterial activity with a 16-68 % reduction in the S. mutans viability. Further, the antibacterial function of the new composite was not affected by human saliva. The aging study indicates that the composite may have a long-lasting antibacterial function. Within the limitations of this study, it appears that the experimental antibacterial resin composite may potentially be developed into a clinically attractive dental restorative due to its high mechanical strength and antibacterial function.


Subject(s)
Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/therapeutic use , Composite Resins/chemistry , Composite Resins/therapeutic use , Dental Restoration, Permanent/methods , Anti-Bacterial Agents/chemical synthesis , Composite Resins/chemical synthesis , Compressive Strength , Humans , In Vitro Techniques , Materials Testing , Microbial Sensitivity Tests , Saliva/physiology , Spectroscopy, Fourier Transform Infrared , Streptococcus mutans/drug effects , Tensile Strength
20.
Am J Dent ; 25(4): 220-6, 2012 Aug.
Article in English | MEDLINE | ID: mdl-23082386

ABSTRACT

PURPOSE: To estimate the surface gloss of various dental nano composites by using the correlation between deltaE* specular component excluded (SCE) - specular component included (SCI) and surface roughness (Ra). METHODS: Two brands of commercial and two experimental light-cured resin composites were used. Resin composite discs were prepared 10 mm in diameter and 3 mm in thickness. 56 subgroups (n=5) were designed according to two different curing conditions (hand light curing and additional post-heat curing) and seven different polishing methods (Mylar, 4000-, 2400-, 1200- and 320- SiC paper, rubber-based silicone, three-step polishing kit). deltaE*SCE-SCI and Ra measurements were done. Two specimens in each subgroup were analyzed by SEM. Multifactorial ANOVA and post hoc Tukey test were applied for the evaluation of the deltaE*SCE-SCI and Ra data (P<0.05). Moreover, Spearman's rank correlation test was used to determine the correlation between deltaE*SCE-SCI and Ra results (P<0.01). RESULTS: A strong correlation was found between deltaE*(SCE-SCI) and Ra results indicating the surface gloss of the tested composite resin materials after different curing and surface polishing methods. A three-factor interaction was found between curing conditions, surface polishing methods and resin composites (P<0.05) in deltaE*SCE-SCI and Ra results. Additionally, significant differences were found between composites and between polishing methods (P<0.05). Furthermore, there were significant differences between curing conditions in Ra results (P<0.05).


Subject(s)
Color , Composite Resins , Nanocomposites , Analysis of Variance , Bisphenol A-Glycidyl Methacrylate , Colorimetry , Composite Resins/chemical synthesis , Composite Resins/chemistry , Dental Polishing/methods , Light-Curing of Dental Adhesives/methods , Nanocomposites/chemistry , Optical Phenomena , Polyethylene Glycols , Polymethacrylic Acids , Spectrophotometry/methods , Statistics, Nonparametric , Surface Properties
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