Preparation and Evaluation of Visible Light-Cured Multi-Methacrylates for Dental Composites

Abstract

To explore new VLC oligomers exhibiting low shrinkage, low water sorption, and improved mechanical properties, a family of multi-methacrylates, based on poly(isopropylidenediphenol) resin (BPA), was synthesized, characterized, and evaluated. The BPA resin, having an average of eight phenolic hydroxyl groups per molecule, was treated with ethylene carbonate and the resultant product esterified at four different grafted levels, using methacryloyl chloride. Structures of these EEBPA oligomers, were confirmed by FT-IR and ¹³C NMR. The EEBPA oligomer/TEGDMA (50/50, w/w) blends were combined with 0.5 wt% camphoroquinone(CQ) and 1.0 wt% N,N-dimethylaminoethyl methacrylate (DMAEM). The control was BisGMA/TEGDMA (50/50, w/w) blends having the same levels of CQ/DMAEM. Differential photocalorimetry (DPC) and differential scanning calorimetry (DSC) showed the multi-methacrylate/TEGDMA (neat resin) blends have polymerization characteristics comparable to the BisGMA/TEGDMA control. These multi-functional oligomers have lower polymerization shrinkage and lower uptake of water and other liquids. In addition, two experimental oligomers EEBPA #2 and #3 have higher compressive strength than the BisGMA and comparable diametral tensile strength to the BisGMA control. These results suggest that the new type of multi-functional methacrylate oligomers (EEBPA) have potential application in formulating dental composites with improved properties.     

Syntheses and evaluation of novel biodegradable amino acid based anhydride polymer resins and composites

A novel synthetic biodegradable oligomer based upon methacrylated aminocaproyl maleamic acid (MACMA), was synthesized and characterized. Injectable and in situ crosslinkable polymer networks were formulated by copolymerization of MACMA with triethyleneglycol dimethacrylate (TEGDMA). In addition, composites composed of MACMA, TEGDMA and beta-tricalcium phosphate (β-TCP) were prepared. The networks and composites were initiated by photo- and redox-polymerization, respectively. The initial compressive (CS) and diametral tensile strengths (DTS) of these materials were determined and used to evaluate the effects of MACMA/TEGDMA ratios on the degradation behavior of the materials. The neat resin networks exhibited initial CS values ranging from 6.7 to 284.2 MPa and the composites demonstrated initial DTS values ranging from 2.8 to 20.8 MPa and CS values ranging from 19.1 to 119.5 MPa. During the course of degradation the polymer neat resins lost 51%, 69% and 61% of their initial CS after 3 weeks for the MACMA/TEGDMA ratios at 25/75, 50/50 and 75/25, respectively. The resin with the MACMA/TEGDMA ratio of 75/25 completely degraded after 6 months. The composite with the MACMA/TEGDMA ratio of 25/75 exhibited a significant increase in CS after an initial decrease for 7 days and then lost 57% of its initial CS after 3 months. The composite composed of poly(MACMA) homopolymer showed a complete degradation after 21 days.     

METHACRYLOYL DERIVITIZED HYPERBRANCHED POLYESTER. 2. PHOTO-POLYMERIZATION AND PROPERTIES FOR DENTAL RESIN SYSTEMS

The purpose of this research is to demonstrate the usefulness of the synthesized hyperbranched multi-methacrylates (H-MMAs) in dental applications. We synthesized three hyperbranched multi-methacrylate oligomers and evaluated them as modifiers for use in the dental resin system: bisphenol A glycidyl dimethacrylate (BisGMA)/tri(ethylene glycol) dimethacrylate (TEGDMA). Their photo-polymerization activities, viscosity, mechanical properties, such as compression, diametral tensile, and flexural strength, were evaluated. H-MMAs (10%) modified dental resins have lower polymerization shrinkage and about 15% increase in mechanical strength compared to the Bis-BisGMA control. For example, H30-MMA has compressive, diametral tensile, and flexural strength of 576, 47, and 85 MPa, compared with the BisGMA control having 497, 43, and 77 MPa. In addition, hyperbranched polymer modified resins have higher glass transition temperature (T_g) and lower thermal expansion coefficient (α) than the control. This research is significant both for increasing our knowledge about hyperbranched multi-functional polymers as well as leading to new dental resin systems with better performance.     

Synthesis and properties of liquid crystalline urethane methacrylates for dental composite applications

Three novel liquid crystalline methacrylates have been synthesized and characterized to be tested as comonomers in light‐curing dental resin‐based composites. The selected formulations consist of an alkylammonium or cholesteryl urethane methacrylate and 2,2‐bis[4‐(2‐hydroxy‐3‐methacryloyloxypropyl)phenyl]propane (BisGMA) or a BisGMA derivate modified with urethane methacrylate groups, further diluted with triethyleneglycol dimethacrylate (TEGDMA) and reinforced with 70% filler (zirconium silicate nanopowder, silanized filler). This study addresses the relationships between the LC monomer structure, photopolymerization rates (by differential scanning photo calorimetry), and specific properties of the dental resin composites (volumetric shrinkage, water sorption, water solubility, and hydrophobicity). The investigation of LC properties by differential scanning calorimetry and polarizing microscopy indicated that the LC mesophase is stable to room temperature (cationic monomers) or at 40 °C (cholesteryl methacrylate). It was found that the polymerization rate for LC urethane methacrylates used in combination with BisGMA/TEGDMA (0.122–0.136 s^?1) is higher than that of the mesogenic monomers alone (0.085–0.107 s^?1). The structures of the urethane monomers and, consequently, the viscosity of the comonomer mixture influence both the rate and the degree of conversion (44.8–67.5 %) of the photopolymerization process. Polymerization shrinkage measured by pycnometry showed lower values for LC monomers (3.25–3.43 vol %) comparatively with the monomer mixture (5.19–6.65 vol %). Preliminarily, the effect of ammonium groups from two resin composites incorporating alkylammonium structures (4.5 wt %) was tested on Streptococcus mutans, and distinct zone of inhibition was observed. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011     

Syntheses of biodegradable polymer networks based on polycaprolactone and glutamic acid

Biodegradable trifunctional oligomer was synthesized from polycaprolactone and glutamic acid and characterized by Fourier‐transform infrared (FTIR) and proton nuclear magnetic resonance (¹H NMR) spectroscopies. Injectable and in situ crosslinkable polymer networks were fabricated by the copolymerization of oligomer with triethylene glycol dimethacrylate (TEGDMA) and used to evaluate the initial compressive strengths, viscosities, shrinkages, thermal stabilities, and biodegradabilities in the forms of polymer network neat resin and their composites with β‐tricalcium phosphate. The initial compressive strengths (CS) values of neat resins ranged from 9.54 to 187.6 MPa. Both neat resins and composites had polymerization shrinkage ranging from 0% to 11.7%, which increased with increasing of TEGDMA contents in resin. Moreover, in polymer composite resins, shrinkage values decreased with increasing filler level from 0% to 4.6%, and exothermic evolution values decreased from 33.5°C to 29.7°C as increasing filler level. The composite with the formulation of (polycaprolactone)‐glutamate triacrylate (PCLGTA)/TEGDMA (25/75) and powder/liquid (P/L) ratio of 1.0 exhibited the highest exothermal and lowest shrinkage values. The increase of oligomer in the formulation led to an increase in viscosity.     

Effect of the Poly(Methyl Methacrylate) Molecular Weight on the Mechanical Properties BisGMA/TEGDMA Semi-interpenetrating Polymer Networks

Abstract

The effect of poly(methyl methacrylate) [PMMA], with different molecular weights on the mechanical properties of a polymerized BisGMA/TEGDMA base monomer resin was investigated. With the aid of acetone solvent, PMMA could be readily dissolved in BisGMA/TEGDMA mixtures. The addition of PMMA can significantly improve the compressive strengths and decrease the Knoop hardness values of the BisGMA/TEGDMA/PMMA semi-IPNs. The thermal expansion coefficients rapidly increased before T_g, and decreased after T _g. The observed properties could be attributed to the effect of the molecular weight of the PMMA on the phase structures of the semi-IPNs.     

Synthesis,characterization and polymerization characteristics of new dimethacrylates,derived from 3,3,5‐trimethylcyclohexan‐1‐one–phenol adducts,as monomers for dental composites

The object of this study was to synthesize, characterize and evaluate several new dimethacrylate monomers, in order to discover new compositions for possible formulation of improved dental restoratives. Dimethacrylates derived from the 3,3,5‐trimethylcyclohexan‐1‐one–phenol reaction products were prepared and characterized by Fourier transform infrared and nuclear magnetic resonance. Thermal‐ and photopolymerization characteristics of these experimental monomers, in blends with triethyleneglycol dimethacrylate (TEGDMA), were evaluated by differential scanning calorimetry and differential photocalorimetry. An additional dimethacrylate derived from the 3,3,5‐trimethylcyclohexanone–phenol adduct, supplied by Bayer AG, was also evaluated during the study. A control for comparison consisted of a 2,2‐bis[4‐(2‐hydroxy‐3‐methacryloyloxy‐propyl) phenyl]propane (BisGMA) blend with TEGDMA. It was found that the polymerization behavior and properties of the visible light‐cured neat resins were dependent on their chemical structures. The experimental resins exhibited comparable curing characteristics, lower water sorption, higher wet glass transition temperature, and other improved properties, compared with the polymerized BisGMA/TEGDMA control. The more rigid and hydrophobic nature of the experimental resins, accomplished by incorporation of the bulky trimethyl‐substituted cyclohexyl moiety in the novel dimethacrylates, was considered to be the major factor contributing to the improved properties. These new dimethacrylates, for formulating thermosets with lower water sorption and higher glass transition temperature, may offer a path to improving composites for a variety of applications, including such things as dental restoratives and bone cements. Copyright © 1999 John Wiley & Sons, Ltd.     

Thermal degradation and isoconversional kinetic analysis of light-cured dimethacrylate copolymers

Thermal degradation kinetics of copolymers based on bis-phenol A ethoxylated dimethacrylate (Bis-EMA) with triethylene glycol dimethacrylate (TEGDMA), and urethane dimethacrylate (UDMA) with TEGDMA in wt/wt ratios 30/70, 50/50, or 70/30 were investigated using thermogravimetric analysis as a means to provide specific information regarding the internal structures of these resins. Thermogravimetric scans were taken at four different heating rates to perform an isoconversional analysis to determine the change of the effective activation energy as a function of conversion. A two-step degradation mechanism was found to occur in almost all copolymer compositions attributed to the existence of inhomogeneities in the macromolecular structure and the formation of weak links inside the polymeric network.     

Preparation of Low-dielectric Permittivity Polyimide Resins with High Surface Activity from Chemically Bonded Hyperbranched Polysiloxane

Thermosetting resin matrix is the key component of advanced wave-transparent composites,where low dielectric constant,excellent processability,high thermal stability,as well as good bonding ability are required for resins.Herein,we prepared a series of phenylethynyl terminated polyimide(PI)resins by grafting amine-functionalized hyperbranched polysiloxane(HBPSi)to PI chains during the in situ polymerization.The effects of HBPSi on the processability of oligomers,molecular packing,thermal stability,dielectric property and bonding ability to reinforce Kevlar fibers of the cured PI/HBPSi composite resins have been examined in detail.The dielectric constants of the cured composite resins were greatly reduced from 3.29 to 2.19 without compromising its processability and thermal stability.Meanwhile,the 10 wt％HBPSi-containing PI resin demonstrated better bonding ability to reinforce fibers with the interfacial shear strength(IFSS)of 37.64 MPa,compared with that of neat PI-6 matrix(27.34 MPa),and better adhesion to metal with the lap shear strength of 10.48 MPa,50％higher than that of neat resin PI-6(6.98 MPa).These resultant PI/HBPSi composite resins exhibit excellent comprehensive properties,indicating their great potential as low-dielectric constant resin matrix in radar radome.     

Hydrogen‐bonding,crystallinity, and morphological properties of poly(silicic acid)/waterborne polyurethane nanocomposites

Unique nanocomposites consisting of poly(silicic acid) nanoparticles (PNs) and waterborne polyurethane (WPU) were prepared. The aliphatic WPU prepared in this study was end‐capped with a silanol group, which could react with PNs via a sol–gel process. PNs were modified with phenyltrimethoxysilane (PTMS) and 3‐(trimethoxysilyl)propyl ester (TMPE) and then blended with WPU. The structure–property relationships were examined. Solid‐state ²⁹Si NMR spectra of WPU showed that structures T₁, T₂, and T₃ of WPU decreased and structures Q₃ and Q₄ of PN/WPU nanocomposites increased gradually. When the PN concentration increased to 10 wt %, PN/WPU nanocomposites exhibited the maximum fraction of hydrogen‐bonded carbonyl groups. In the PTMS–PN and TMPE–PN systems, the fraction of hydrogen‐bonded carbonyl groups fluctuated stably when the concentrations of PTMS–PN and TMPS–PN exceeded 5 wt %. The X‐ray diffraction results revealed that α‐form, γ‐form, or triclinic crystallization could be found in the WPU matrix. A differential scanning calorimetry spectrum showed that the crystalline structure of the hard segment of WPU was influenced by the nanoparticle concentration. The degrees of crystallinity were 88% for the PN/WPU nanocomposites, 41% for the PTMS–PN/WPU nanocomposites, and 54% for the TMPE–PN/WPU nanocomposites when the PN, PTMS–PN, and TMPE–PN concentrations were 5 wt %. © 2005 Wiley Periodicals, Inc. J Polym Sci Part B: Polym Phys 43: 1076–1089, 2005     

Characterization of dimethacrylate polymeric networks: a study of the crosslinked structure formed by monomers used in dental composites

The resin phase of dental composites is mainly composed of combinations of dimethacrylate comonomers, with final polymeric network structure defined by monomer type/reactivity and degree of conversion. This fundamental study evaluates how increasing concentrations of the flexible triethylene glycol dimethacrylate (TEGDMA) influences void formation in bisphenol A diglycidyl dimethacrylate (BisGMA) co-polymerizations and correlates this aspect of network structure with reaction kinetic parameters and macroscopic volumetric shrinkage. Photopolymerization kinetics was followed in real-time by a near-infrared (NIR) spectroscopic technique, viscosity was assessed with a viscometer, volumetric shrinkage was followed with a linometer, free volume formation was determined by positron annihilation lifetime spectroscopy (PALS) and the sol–gel composition was determined by extraction with dichloromethane followed by ¹H NMR analysis. Results show that, as expected, volumetric shrinkage increases with TEGDMA concentration and monomer conversion. Extraction/¹H NMR studies show increasing participation of the more flexible TEGDMA towards the limiting stages of conversion/crosslinking development. As the conversion progresses, either based on longer irradiation times or greater TEGDMA concentrations, the network becomes more dense, which is evidenced by the decrease in free volume and weight loss after extraction in these situations. For the same composition (BisGMA/TEGDMA 60–40 mol%) light-cured for increasing periods of time (from 10 to 600 s), free volume decreased and volumetric shrinkage increased, in a linear relationship with conversion. However, the correlation between free volume and macroscopic volumetric shrinkage was shown to be rather complex for variable compositions exposed for the same time (600 s). The addition of TEGDMA decreases free-volume up to 40 mol% (due to increased conversion), but above that concentration, in spite of the increase in conversion/crosslinking, free volume pore size increases due to the high concentration of the more flexible monomer. In those cases, the increase in volumetric shrinkage was due to higher functional group concentration, in spite of the greater free volume. Therefore, through the application of the PALS model, this study elucidates the network formation in dimethacrylates commonly used in dental materials.     

Molecular motion,morphology, and thermal properties of multiwall carbon nanotube/polysilsesquioxane composite

Diglycidyl ether of bisphenol A (DGEBA)‐bridged polyorganosiloxane precursors have been prepared successfully by reacting diglycidyl ether of bisphenol A epoxy resin with 3‐aminopropyltriethoxysilane. Acid‐modified and unmodified multiwalled carbon nanotube (MWCNT) were dispersed in the diglycidyl ether of bisphenol A‐bridged polyorganosiloxane precursors and cured to prepare the carbon nanotube/diglycidyl ether of bisphenol A‐bridged polysilsesquioxane (MWCNT/DGEBA‐PSSQ) composites. The molecular motion of MWCNT/DGEBA‐PSSQ nanocomposites was studied by high‐resolution solid‐state ¹³C NMR. Acid‐modification can improve the affinity between MWCNT and the polymer matrix. The molecular motion of the DGEBA‐PSSQ decreased with acid‐modified MWCNT content. However, when unmodified MWCNT was used, the molecular motion of the DGEBA‐PSSQ was increased. SEM and TEM microphotographs confirm that acid‐modified MWCNT exhibits better dispersion than unmodified MWCNT in DGBEA‐PSSQ. The dynamic mechanical properties of acid‐modified MWCNT/DGBEA‐PSSQ composites are more favorable than those of unmodified MWCNT. T_g of the DGEBA‐PSSQ decreased from 174.0 °C (neat DGEBA‐PSSQ) to 159.0 °C (1 wt % unmodified MWCNT) and 156.0 °C (1 wt % acid‐modified MWCNT). The storage modulus (at 30 °C) of the DGEBA‐PSSQ increased from 1.23 × 10⁹ Pa (neat DGEBA‐PSSQ) to 1.65 × 10⁹ Pa (1 wt % acid‐modified MWCNT). However, when unmodified MWCNT was used, the storage modulus of the DGEBA‐PSSQ decreased to 6.88 × 10⁸ Pa (1 wt % unmodified MWCNT). At high temperature, above 150 °C, storage modulus of nanocomposites was higher than that of neat polymer system. © 2008 Wiley Periodicals, Inc. J Polym Sci Part B: Polym Phys 46: 472–482, 2008     

Free volume hole size of Cyanate ester resin/Epoxy resin interpenetrating networks and its correlations with physical properties

Cyanate ester (CE) resin was blended with epoxy resin (EP) at different mass ratios (CE/EP: 100/0, 90/10, 70/30, 50/50, 30/70, 10/90, and 0/100). The curing process of the blend system was characterized by Fourier transform infrared spectrometry (FTIR) and differential scanning calorimetry (DSC). Examination of the mechanical properties, thermal stability, and morphology of the blend systems showed that addition of epoxy resin resulted in improved toughness but a little sacrifice in thermal stability when compared with neat CE. The free volume size of the blend system determined by positron annihilation lifetime spectroscopy (PALS) decreased with the epoxy resin content, which is consistent with the chemical structure changes for the copolymerization between CE and EP. The crosslinking units of curing products (oxazoline, oxazolidinone, and polyether network) of the blends are all smaller in size than those of triazine ring structure from neat CE. Therefore, the free volume size of the blends decreases with increase of EP content. The correlations between the free volume properties and other physical properties (thermal stability and mechanical properties) have also been discussed.     

Direct patterning of poly(amic acid) and low‐temperature imidization using a crosslinker,a photoacid generator,and a thermobase generator

A positive‐type photosensitive polyimide (PSPI) based on poly(amic acid) (PAA), a crosslinker 1,1,1‐tris{4‐[2‐(vinyloxy)ethoxy]phenyl}ethane (TVPE), a photoacid generator (PAG) (5‐propylsulfonyloxyimino‐5H‐thiophen‐2‐ylidene)‐2‐(methylphenyl)acetonitrile (PTMA), and a thermobase generator (TBG) t‐butyl 2,6‐dimethylpiperidine‐1‐carboxylate (BDPC) has been developed as a promising material in microelectronics. The PAA was prepared from 3,3′,4,4′‐biphenyltetracarboxylic dianhydride (BPDA) and 4,4′‐oxydianiline (ODA) in dimethyl sulfoxide (DMSO). The PSPI, consisting of PAA (69 wt %), TPVE (21 wt %), PTMA (3 wt %), and BDPC (7 wt %), showed high sensitivity of 21 mJ/cm² and a high contrast of 6.8 when it was exposed to a 436‐nm line (g‐line), postbaked at 90 °C for 5 min, and developed with 1.69 wt % TMAHaq. A clear positive image of 8 μm line and space pattern was printed on film, which was exposed to 50 mJ/cm² of g‐line by a contact printing mode and fully converted to the corresponding polyimide (PI) pattern on heating at 200 °C, confirmed by FTIR spectroscopy. Thus, this system will be a good candidate for next generation PSPIs. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 3362–3369, 2009     

Structural,dielectric and conductivity behaviours of cetyltrimethylammonium bromide/ethylene glycol-based quenched lyotropic mesophases

The present study highlights the effect of quenching on the structural, textural and dielectric dynamics of cetyltrimethylammonium bromide/ethylene glycol binary mixtures of varying concentrations 30:70, 50:50 and 75:25 wt.%. No mesomorphism is seen in the as-prepared binary mixtures as X-ray diffraction and polarisation optical microscopy studies reveal the crystalline-like structures for the studied concentrations. With the effect of quenching, lyotropic hexagonal phase is obtained at 30:70, 50:50 wt.% concentration; however, mixture with higher 75:25 wt.% concentrations exhibit crystalline-like phase. The obtained hexagonal lyotropic phases restrain the mesomorphism up to ≈340 K and then show crystalline-like structures with the further increase in the temperature. Dielectric and relaxation behaviours of hexagonal lyotropic phases are presented in this study. The relaxation parameters of lyotropic phases are also discussed. Interestingly, the hexagonal lyotropic phases obtained for 30:70 and 50:50 wt.% concentrations exhibit ac conductivity of the order of 10^–5 S/m, which can be seen as a significant result of this study.     

METHACRYLOYL DERIVITIZED HYPERBRANCHED POLYESTER. 1. SYNTHESIS,CHARACTERIZATION, AND COPOLYMERIZATION

Three hyperbranched multi-methacrylates (H20-MMA, H30-MMA and H40-MMA) have been synthesized by reacting Boltorn dendritic polyols with methacrylic anhydride and methacryloyl chloride. Their structures were characterized by FT-IR and NMR (¹H and ¹³C) and molecular weights were measured by GPC. These multi-methacrylates (H-MMAs) mixed well with a variety of monomers such as acrylic acid (AA), methacrylic acid (MA), methyl methacrylate (MMA), 2-hydroxy-ethyl methacrylate (HEMA), tri(ethylene glycol) dimethdimethacrylate (TEGDMA), and bisphenol A glycidyl dimethacrylate (BisGMA). The initial studies on thermal polymerization activities of 10% of H-MMAs with AA, MA, and MMA showed that they gave higher polymerization enthalpy than the corresponding homopolymerization. The resulting materials showed one glass transition temperature, indicating a typical single-phase resin. The H-MMAs can effectively copolymerize with AA, MA, and MMA, with essentially no homopolymers produced, as indicated by acetone extraction studies. This indicated that the hyperbranched multi-methacrylates have the potential to be used as crosslinking agents or modifiers with a number of monomers to produce new thermosets.     

Resin impregnation of cellulose nanofibril films facilitated by water swelling

Flexible composite films were produced by impregnating aqueous phenol formaldehyde (PF) resin into water-swollen cellulose nanofibril (CNF) films. CNF films were prepared using a pressurized filtration method in combination with freeze drying. The freeze-dried films were swollen with water then impregnated with PF resin by soaking in aqueous resin solutions of varying concentrations. Small amounts of PF slightly enhanced the tensile properties of CNF films. The formulation with the best mechanical properties was CNF/PF films with 8 wt % resin exhibiting tensile stress and toughness of 248 MPa and 26 MJ/m³, respectively. Resin concentrations higher than about 8 % resulted in composites with decreased tensile properties as compared to neat CNF films. The wet strength of the composite films was significantly higher than that of the neat CNF films. The resulting composites showed greater resistance to moisture absorption accompanied by reduced thickness swelling when soaked in water as compared to neat CNF films. The composites also showed decreased oxygen permeability at low humidity compared to neat films, but the composites did not show improved barrier properties at high humidity.     

Synthesis and photopolymerization of piperonylamine derivatives as a polymerizable cyclic acetals co‐initiator for light‐cured unfilled dental resins

The aim of this study was to synthesize and characterize N,N‐di(methacryly‐ethoxycarbonyl‐ethyl)‐N‐(1,3‐benzodioxole‐ 5‐methylene)(DMEBM) to replace both triethylene glycol dimethylacrylate(TEGDMA) as a dilute and the non‐polymerizable amine, which is added as a co‐initiator in dental resin mixtures. 2,2‐bis[4‐(2‐Hydroxy‐3‐methacryloxypropoxy) phenyl]‐propane (Bis‐GMA) and camphorquinone (CQ) were used as monomer and photoinitiator in these model dental resin systems, in contrast to ethyl 4‐dimethylaminobenzoate (EDMAB) which was usually used as a co‐initiator. DMEBM was synthesized via Michael‐Addition reaction and characterized using ¹H NMR spectroscopy. A mixture of Bis‐GMA/DMEBM/CQ was found to reach the double bond conversion of 67.5%, slightly higher than that of Bis‐GMA/TEGDMA/CQ/EDMAB (66.8%) and Bis‐GMA/TEGDMA/CQ/DMEBM (64.8%). In addition, the glass transition temperature of Bis‐GMA/TEGDMA/CQ/EDMAB (93.4°C) were higher than that of Bis‐GMA/TEGDMA/CQ/DMEBM (89.3 °C) and Bis‐GMA/DMEBM/CQ (80.4°C). The water sorption and solubility of Bis‐GMA/TEGDMA/CQ/DMEBM were higher than that of Bis‐GMA/TEGDMA/CQ/EDMAB and Bis‐GMA/DMEBM/CQ. However, the values were still within the range of the ISO 4049 standards. DMEBM could be used as a potential co‐initiator and diluent for dental composite. Copyright © 2009 John Wiley & Sons, Ltd.     

The Curing Efficiency and Mechanical Properties of Light-Activated Acrylic Resin

The aim of this investigation was to determine degree of conversion, and flexural and compressive strength of photocurable acrylic resin. The acrylic resins based on bis-phenol A glycidyl dimethacrylate (BisGMA) and triethylene glycol dimethacrylate (TEGDMA) were formulated and then irradiated with red light to form a solid crosslinked polymer. Various post curing conditions were studied to investigate their effects on curing efficiency. Degree of conversion was analyzed by means of Fourier Transform Infrared Spectroscopy (FTIR) to monitor the quantity of remaining acrylic double bond in the cured resin. Three-point bending and compressive strength were tested using Universal Testing Machine (UTM) to evaluate the mechanical performance. Our investigation demonstrated that the formulated acrylic resins were possibly polymerized under irradiation with red light and degree of conversion and mechanical properties were closely correlated.     

Supercritical fluid extraction for the separation of organochlorine pesticides residue in Angelica sinensis

A method involving the simultaneous extraction and separation of 12 organochlorine pesticides (OCPs) from Angelicae sinensis was developed using supercritical fluid extraction (SFE). The pesticides in the study were alpha-, beta-, gamma- and delta-benzene hexachloride, PCNB (pentachloro- nitrobenzene), PCA (pentachloroaniline), HEPT (heptachlor), MPCPS (methyl-pentachlorophenyl sulfide), pp'-DDE [1,1-dichloro-2,2-bis (p-chlorophenyl) ethylene], op'-DDT [1,1,1,-trichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl) ethane], pp'-DDD [1,1-dichloro-2,2-bis(p-chlorophenyl) ethane], and pp'-DDT [1,1,1,-trichloro-2,2-bis (p-chlorophenyl)ethane]. The extraction conditions were optimized as follows: pure CO(2), extraction pressure 15 MPa, extraction temperature 60 degrees C, extraction time 20 min, and flow-rate 1.5 mL/min. A GC method with electron capture detection was employed to determine the OCPs in Angelicae sinensis. An HPLC method was developed for the quantitative determination of active constituents. The SFE provided high decontamination rate of OCPs and low loss of active constituents in Angelicae sinensis.