scholarly journals Novel Urethane-Dimethacrylate Monomers and Compositions for Use as Matrices in Dental Restorative Materials

2020 ◽  
Vol 21 (7) ◽  
pp. 2644 ◽  
Author(s):  
Izabela M. Barszczewska-Rybarek ◽  
Marta W. Chrószcz ◽  
Grzegorz Chladek
Keyword(s):  
Water Sorption ◽  
Water Solubility ◽  
Triethylene Glycol ◽  
Degree Of Conversion ◽  
Dental Composite ◽  
Polymerization Shrinkage ◽  
Dental Restorative Materials ◽  
Restorative Materials ◽  
Urethane Dimethacrylate ◽  
Dental Restorative

In this study, novel urethane-dimethacrylate monomers were synthesized from 1,3-bis(1-isocyanato-1-methylethyl)benzene (MEBDI) and oligoethylene glycols monomethacrylates, containing one to three oxyethylene groups. They can potentially be utilized as matrices in dental restorative materials. The obtained monomers were used to prepare four new formulations. Two of them were solely composed of the MEBDI-based monomers. In a second pair, a monomer based on triethylene glycol monomethacrylate, used in 20 wt.%, was replaced with triethylene glycol dimethacrylate (TEGDMA), a reactive diluent typically used in dental materials. For comparison purposes, two formulations, using typical dental dimethacrylates (bisphenol A glycerolate dimethacrylate (Bis-GMA), urethane-dimethacrylate (UDMA) and TEGDMA) were prepared. The monomers and mixtures were tested for the viscosity and density. The homopolymers and copolymers, obtained via photopolymerization, were tested for the degree of conversion, polymerization shrinkage, water sorption and solubility, hardness, flexural strength and modulus. The newly developed formulations achieved promising physico-chemical and mechanical characteristics so as to be suitable for applications as dental composite matrices. A combination of the MEBDI-based urethane-dimethacrylates with TEGDMA resulted in copolymers with a high degree of conversion, low polymerization shrinkage, low water sorption and water solubility, and good mechanical properties. These parameters showed an improvement in relation to currently used dental formulations.

scholarly journals Monomers used in resin composites: degree of conversion, mechanical properties and water sorption/solubility

2012 ◽  
Vol 23 (5) ◽  
pp. 508-514 ◽  
Author(s):  
Vinícius E. S. Gajewski ◽  
Carmem S. Pfeifer ◽  
Nívea R. G. Fróes-Salgado ◽  
Letícia C. C. Boaro ◽  
Roberto R. Braga
Keyword(s):  
Mechanical Properties ◽  
Water Sorption ◽  
Flexural Modulus ◽  
Triethylene Glycol ◽  
Degree Of Conversion ◽  
Resin Composites ◽  
Triethylene Glycol Dimethacrylate ◽  
Three Point Bending ◽  
Rate Of Polymerization ◽  
Urethane Dimethacrylate

The organic phase of resin composites is constituted by dimethacrylate resins, the most common monomers being the bisphenol A diglycidildimethacrylate (BisGMA), its ethoxylated version (BisEMA), triethylene glycol dimethacrylate (TEGDMA) and urethane dimethacrylate (UDMA). This study compared the homopolymers formed from the monomers used in restorative dental composites in terms of their degree of conversion (DC) and reaction kinetics (by near infra-red spectroscopy, n=3), mechanical properties (flexural modulus and strength in three point-bending, FM and FS, respectively, n=15), water sorption and solubility (WS and SL, respectively - ISO 4049, n=5). Materials were made photopolymerizable by the addition of camphoroquinone/dimethylamine ethyl methacrylate. TEGDMA showed the highest DC, followed by BisEMA, UDMA and BisGMA, both at 10 min and at 24h (p<0.001). UDMA showed the highest rate of polymerization, followed by TEGDMA, BisEMA and BisGMA (H0=13.254, p<0.001). UDMA and TEGDMA presented similar FM, significantly higher (p<0.001) than BisEMA and BisGMA, which in turn present statistically similar values (p>0.001). For FS, UDMA presented the highest value (p<0.001), followed by TEGDMA, then by BisEMA and BisGMA, which were statistically similar (p>0.001). BisGMA showed the highest WS, and TEGDMA and BisEMA the lowest. UDMA was statistically similar to all (H0=16.074, p<0.001). TEGDMA presented the highest SL, followed by UDMA, BisGMA and BisEMA (p<0.001). The tested homopolymers presented different behaviors in terms of polymerization kinetics, flexural properties, water sorption and solubility. Therefore, the use of copolymers is justified in order to obtain high DC and mechanical properties, as well as good resistance to water degradation.

scholarly journals Novel dental restorative materials having low polymerization shrinkage stress via stress relaxation by addition-fragmentation chain transfer

2012 ◽  
Vol 28 (11) ◽  
pp. 1113-1119 ◽  
Author(s):  
Hee Young Park ◽  
Christopher J. Kloxin ◽  
Ahmed S. Abuelyaman ◽  
Joe D. Oxman ◽  
Christopher N. Bowman
Keyword(s):  
Stress Relaxation ◽  
Chain Transfer ◽  
Shrinkage Stress ◽  
Polymerization Shrinkage ◽  
Dental Restorative Materials ◽  
Restorative Materials ◽  
Dental Restorative

A triethylene glycol dimethacrylate- free dental composite for reduced water-sorption and shrinkage

2017 ◽  
Vol 52 (12) ◽  
pp. 1579-1588 ◽  
Author(s):  
Yuling Xu ◽  
Dong Xie
Keyword(s):  
Water Sorption ◽  
Triethylene Glycol ◽  
Dental Composite ◽  
Dental Composites ◽  
Screen Tool ◽  
Glycol Dimethacrylate ◽  
Triethylene Glycol Dimethacrylate ◽  
Commercial Resin ◽  
Urethane Dimethacrylate ◽  
Reduced Water

A number of new liquid urethane-based oligomers were synthesized, characterized and used to formulate the dental composites. Compressive strength and viscosity were used as a screen tool to evaluate the formed composites. Commercial available bisphenol A glycidyl methacrylate and urethane dimethacrylate-based systems were used as controls. Degree of conversion, shrinkage, water-sorption, solubility, flexural strength and diametrial tensile strength were evaluated. The results show that using mixed acrylate/methacrylate or methacrylates with different length to derivatize diisocyanates could be a good strategy to synthesize urethane-based oligomers in a liquid state. The developed triethylene glycol dimethacrylate-free urethane-based composites showed significantly reduced water sorption and solubility, decreased shrinkage and enhanced mechanical strength as compared to commercial resin-based ones.

scholarly journals Enhancing Toughness and Reducing Volumetric Shrinkage for Bis-GMA/TEGDMA Resin Systems by Using Hyperbranched Thiol Oligomer HMDI-6SH

Materials ◽  
2021 ◽  
Vol 14 (11) ◽  
pp. 2817
Author(s):  
Biao Yu ◽  
Jingwei He ◽  
Sufyan Garoushi ◽  
Pekka K. Vallittu ◽  
Lippo Lassila
Keyword(s):  
Water Sorption ◽  
Water Solubility ◽  
Click Reaction ◽  
Raw Materials ◽  
Triethylene Glycol ◽  
Bending Test ◽  
Volumetric Shrinkage ◽  
Dental Resin ◽  
System A ◽  
Double Bond Conversion

In order to improve the toughness and reduce polymerization shrinkage of traditional bisphenol A-glycidyl methacrylate (Bis-GMA)/triethylene glycol dimethacrylate (TEGDMA) based dental resin system, a hyperbranched thiol oligomer (HMDI-6SH) was synthesized via thiol-isocyanate click reaction using pentaerythritol tetra(3-mercaptopropionate (PETA) and dicyclohexylmethane 4,4′-diisocyanate (HMDI) as raw materials. Then HMDI-6SH was mixed with 1,3,5-Triallyl-1,3,5-Triazine-2,4,6(1H,3H,5H)-Trione (TTT) to prepare thiol-ene monomer systems, which were added into Bis-GMA/TEGDMA resins with different mass ratio from 10 wt% to 40 wt% to serve as anti-shrinking and toughening agent. The physicochemical properties of these thiol-ene-methacrylate ternary resins including functional groups conversion, volumetric shrinkage, flexural properties, water sorption, and water solubility were evaluated. The results showed that the incorporation of HMDI/TTT monomer systems into Bis-GMA/TEGDMA based resin could improve C=C double bond conversion from 62.1% to 82.8% and reduced volumetric shrinkage from 8.53% to 4.92%. When the mass fraction of HMDI/TTT monomer systems in the resins was no more than 20 wt%, the flexural strength of the resin was higher or comparable to Bis-GMA/TEGDMA based resins (p > 0.05). The toughness (it was measured from the stress–strain curves of three-point bending test) of the resins was improved. Water sorption and water solubility tests showed that the hydrophobicity of resin was enhanced with increasing the content of thioester moiety in resin.

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