Synthesis, characterization, and cure reaction of methacrylate-based multifunctional monomers for dental composites (original) (raw)
Related papers
Advances in Polymer Technology, 2014
The objective of this study was to synthesize a dual-functional light curable resin by the reaction between acrylated cycloaliphatic epoxy resin and 3-isocyanatopropyltrimethoxysilane and investigate the performance of this oligomer in the preparation of resin-based composite restoratives. FT-IR and 29 Si-NMR were used to characterize the structure of the hybrids. The char yields of the hybrids increased with inorganic content comes from TEOS (tetraethylorthosilicate) and synthesized SiUA oligomers. Gel content of polymeric films was found to be between 95% and 98%. Swelling was found to be between 3.1% and 3.8%. Weight loss of coated human teeth in synthetic saliva solution was found to be among 1% and 2%. There was a systematic increase in the modulus and tensile strength with the increase of inorganic content. On the other hand, elongation at break did not changed. Prepared hybrid coating materials exhibited improvement in tensile properties and hardness, when photo chemically cured.
Composite resins based on novel and highly reactive bisglycidyl methacrylate monomers
Journal of Applied Polymer Science, 2014
ABSTRACTThree new bisglycidyl monomers; 1,4‐bis((2‐hydroxy‐3‐methacryloxypropoxy) methyl)benzene (MB‐Phe‐OH), 1,4‐bis(2‐hydroxy‐3‐methacryloxypropoxy)2‐cis‐butene (MB‐Cis‐OH), and 1,7‐bis(2‐hydroxy‐3‐methacryloxypropoxy)heptane (MB‐1,7‐OH); were synthesized and used as Bis‐GMA/TEGDMA (bisphenolglycidyl methacrylate/triethylene glycol dimethacrylate) composite resin additives. Flexural properties and double bond conversion of the dental resins composed of silanizated inorganic filler and organic matrices containing new monomers were evaluated. The composite resins formulated, using the monomers MB‐Cis‐OH and MB‐1,7‐OH, have mechanical properties and double bond conversion comparable with those of Bis‐GMA/TEGDMA composite resin used as control. The composite containing the new monomer MB‐Phe‐OH has better flexural properties (flexural strength 65.01 MPa and flexural modulus 5675.91 MPa) than the control composite resin (flexural strength 52.85 MPa and flexural modulus 4879.72 MPa); th...
Synthesis and evaluation of novel dental monomer with branched aromatic carboxylic acid group
Journal of Biomedical Materials Research Part B: Applied Biomaterials, 2012
A new glycerol-based dimethacrylate monomer with an aromatic carboxylic acid, 2-((1,3-bis(methacryloyloxy)propan-2-yloxy)carbonyl)benzoic acid (BMPB), was synthesized, characterized, and proposed as a possible dental co-monomer for dentin adhesives. Dentin adhesives containing 2-hydroxyethyl methacrylate (HEMA) and 2,2-bis[4-(2-hydroxy-3-methacryloxypropoxy) phenyl]propane (BisGMA) in addition to BMPB were formulated with water at 0, 5, 10, and 15 wt % to simulate wet, oral conditions, and photo-polymerized. Adhesives were characterized with regard to viscosity, real-time photopolymerization behavior, dynamic mechanical analysis, and microscale 3D internal morphologies and compared with HEMA/BisGMA controls. When formulated under wet conditions, the experimental adhesives showed lower viscosities (0.04-0.07 Pa s) as compared to the control (0.09-0.12 Pa s). The experimental adhesives showed higher glass transition temperature (146-157 C), degree of conversion (78-89%), and rubbery moduli (33-36 MPa), and improved water miscibility (no voids) as compared to the controls (123-135 C, 67-71%, 15-26 MPa, and voids, respectively). The enhanced properties of these adhesives suggest that BMPB with simple, straightforward synthesis is a promising photocurable co-monomer for dental restorative materials. V C 2011 Wiley Periodicals, Inc. J Biomed Mater Res Part B: Appl Biomater 100B: 569-576, 2012. How to cite this article: Park J, Ye Q, Singh V, Kieweg SL, Misra A, Spencer P. 2012. Synthesis and evaluation of novel dental monomer with branched aromatic carboxylic acid group. J Biomed Mater Res Part B 2012:100B:569-576. V C 2011 WILEY PERIODICALS, INC.
Dental Materials, 2009
Objective-This study evaluates the performance of highly reactive novel monomethacrylates characterized by various secondary moieties as reactive diluent alternatives to TEGDMA in BisGMA filled dental resins. We hypothesize that these monomers improve material properties and kinetics over TEGDMA because of their unique polymerization behavior. Methods-The cure rates and final double bond conversion of the resins were measured using realtime FTIR spectroscopy. The glass transition temperature and storage modulus of the formed polymers were measured using dynamic mechanical analysis. Flexural modulus and flexural strength values were obtained using a three-point bending flexural test carried out with a MTS ® 858 Mini Bionix system. Results-Polymerization kinetics and polymer mechanical properties were evaluated for the novel resin composites. It was observed that upon the use of novel monomethacrylates as reactive diluents, polymerization kinetics increased by up to 3-fold accompanied by increases in the extent of cure from 5% to 13% as compared to the BisGMA/TEGDMA control. Polymer composites formed from resins of BisGMA/novel monomethacrylates exhibited comparable T g values to the control, along with 27-37% reductions in the glass transition half widths indicating the formation of more homogeneous polymeric networks. The BisGMA/monomethacrylate formulations exhibited equivalent flexural modulus and flexural strength values relative to BisGMA/TEGDMA. Significance-Formulations containing novel monovinyl methacrylates exhibit dramatically increased curing rates while also exhibiting superior or at least comparable composite polymer mechanical properties. Thus, these types of materials are attractive for use as reactive diluent alternatives to TEGDMA in dental formulations.
Methacrylate Polymers With “Flipped External” Ester Groups: A Review
Frontiers in Dental Medicine
Current resin composites have favorable handling and upon polymerization initial physical properties that allow for efficient material replacement of removed carious tooth structure. Dental resin composites have long term durability limitations due to the hydrolysis of ester bonds within the methacrylate based polymer matrix. This article outlines the importance of ester bonds positioned internal to the carbon-carbon double bond in current methacrylate monomers. Water and promiscuous salivary/bacterial esterase activity can initiate ester bond hydrolysis that can sever the polymer backbone throughout the material. Recent studies have custom synthesized, with the latest advances in modern organic chemical synthesis, a novel molecule named ethylene glycol bis (ethyl methacrylate) (EGEMA). EGEMA was designed to retain the reactive acrylate units. Upon intermolecular polymerization of vinyl groups, EGEMA ester groups are positioned outside the backbone of the polymer chain. This review ...
Journal of Applied Polymer Science, 2016
In this study, a new biobased isosorbide urethane methacrylic monomer [isosorbide-derived urethane dimethacrylate (Is-UDMA)] was evaluated as a replacement for currently used bisphenol A glycerolate dimethacrylate (Bis-GMA) based dental restorative materials. Dental composites were prepared at different Is-UDMA and Bis-GMA concentrations. For these composites, the photocuring kinetics, volumetric shrinkage, viscoelastic properties, water sorption, and solubility were evaluated. The photocuring kinetics, followed by real-time IR spectroscopy, showed higher double-bond conversion (DC) values for the formulations containing the Is-UDMA monomer; the highest DC (82%) was achieved by the formulation prepared with only the Is-UDMA monomer. The volumetric shrinkage was reduced to 23.7% as compared with the dental resin formulated with Bis-GMA. The viscoelastic properties of the formulations containing both Is-UDMA and Bis-GMA monomers in a 50:50 composition were superior to the rest of the tested formulations, including those prepared with pure polymers. This behavior was explained in terms of a compromise between crosslinking and rigidity (or flexibility) of the resulting polymer network. A preliminary test on microleakage in a dental enamel demonstrated that the new Is-UDMA monomer is a potential replacement for the Bis-GMA monomer in dental restorative materials.
Synthesis and characterization of curable methacrylate-based monomers
Journal of Applied Polymer Science, 2010
The synthesis of new methacrylate-based, curable macromonomers, 4,4′-bis[2-hydroxy-3-aminopropylmethacrylate] diphenyl ether (BHAPE) and 4,4′-bis[2-hydroxy-3-aminopropylmethacrylate] diphenyl methane (BHAPM), is reported. BHAPE and BHAPM were prepared by the reaction of glycidyl methacrylate (GMA) with 4,4′-diaminodiphenyl ether and 4,4′-diaminodiphenyl methane, respectively. The progress of the reaction was monitored by thin-layer chromatography (TLC), and the structure of the monomers was characterized by Fourier transform infrared (FTIR) and 1H-NMR spectroscopy. Thermal curing of the monomers was conducted in a differential scanning calorimeter (DSC) with peroxide as the initiator. Thermal curing of the monomers showed the highest rate at 100°C with the activation energy value in the range 80–90 kJ distilled/mol. The water absorption properties of the cured samples in water, acidic, and basic solutions were studied. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2010
Development of reactive methacrylates based on glycidyl methacrylate
Journal of Polymer …, 2010
Six methacrylate monomers have been synthesized for use as reactive diluents in dental composites and evaluated to investigate the relationship between molecular structure and monomer reactivity. Four were synthesized by reactions of glycidyl methacrylate (GMA) with various acids, 2-(2-methoxyethoxy)acetic acid (1), 2-(2-(2-methoxyethoxy)ethoxy)acetic acid (2), cyanoacetic acid , and benzoic acid (4); others were synthesized by reactions of GMA with diethyl hydrogen phosphate (5) or methanol . Monomers 1 and 2 are novel, 3 seems to be novel, 4 and 6 were synthesized via a novel method, and the synthesis of 5 was described in the literature. The monomers showed high crosslinking tendencies during thermal bulk polymerizations. The photo-, homo-, and copolymerization behavior of the monomers with 2,2-bis[4-(2-hydroxy-3-methacryloyloxy)phenyl]propane (Bis-GMA) were investigated. The maximum rate of polymerizations of monomers 2-6 was found to be greater than triethyleneglycol dimethacrylate, Bis-GMA, 2-hydroxyethyl methacrylate, and glycerol dimethacrylate. For the more reactive monomers , the oxygen sensitivity of polymerization was found to be low due to a hydrogen abstraction/chain transfer reaction. The computationally calculated dipole moment and lowest unoccupied molecular orbital energies indicated that there seems to be a correlation between these quantities and reactivity for ester linked monomers (1-5), which was also supported by 13 C NMR data.