Viscosity, Degree of Polymerization, Water Uptake, and Water Solubility Studies on Experimental Dichloro-BisGMA-Based Dental Composites

The objective of this work was to investigate the advantages of using dichloro bisphenol A-glycidyl methacrylate (dCl-BisGMA) as a potential matrix for dental resin composites. A series of model composites containing 65 wt% resin (urethane dimethacrylate/triethylene glycol dimethacrylate/BisGMA as 1:3:1) and 35 wt% silanated silica were prepared. Thus, BisGMA was replaced by dCl-BisGMA as 0, 25, 50, and 100 wt% to obtain UTBC0, UTBC25, UTBC50, and UTBC100, respectively. The composites’ rheological properties, degree of double-bond conversion (DC), water sorption (WSP), and water solubility (WSL) were examined. The data revealed a statistically significant reduction in the complex viscosity of composites containing dCl-BisGMA, compared with UTBC0. No significant differences between DCs were detected (p < 0.05). A significant enhancement in the reduction of the dCl-BisGMA composite WSP was also detected, and conversely, WSL was increased. Although the viscosity, DC, and WSP characters were enhanced, a WSL increase is an undesirable development. However, WSL is supposedly caused by cyclization of small flexible chains, which is more likely to occur in the presence of hydrophobic monomers such as dCl-BisGMA and more prone to leaching than are crosslinked networks. We concluded that dCl-BisGMA is a monomer that could potentially be used as an alternative or in combination with traditional monomers, including BisGMA, in resin-based dental composites, and it deserves further investigation.

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

Materials ◽

10.3390/ma14112817 ◽

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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Controlled Release of Chlorhexidine from UDMA-TEGDMA Resin

Journal of Dental Research ◽

10.1177/154405910608501016 ◽

2006 ◽

Vol 85 (10) ◽

pp. 950-954 ◽

Cited By ~ 52

Author(s):

K.J. Anusavice ◽

N.-Z. Zhang ◽

C. Shen

Keyword(s):

Triethylene Glycol ◽

Filler Loading ◽

Degree Of Polymerization ◽

Fickian Diffusion ◽

Release Mechanism ◽

Glycol Dimethacrylate ◽

Release Rates ◽

Triethylene Glycol Dimethacrylate ◽

Urethane Dimethacrylate ◽

Dental Applications

Chlorhexidine salts are available in various formulations for dental applications. This study tested the hypothesis that the release of chlorhexidine from a urethane dimethacrylate and triethylene glycol dimethacrylate resin system can be effectively controlled by the chlorhexidine diacetate content and pH. The filler concentrations were 9.1, 23.1, or 33.3 wt%, and the filled resins were exposed to pH 4 and pH 6 acetate buffers. The results showed that Fickian diffusion was the dominant release mechanism. The rates of release were significantly higher in pH 4 buffer, which was attributed to the increase of chlorhexidine diacetate solubility at lower pH. The higher level of filler loading reduced the degree of polymerization, leading to a greater loss of organic components and higher chlorhexidine release rates.

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Correlation between the degree of conversion and the elution of leachable components from dental resin-based cements

Journal of the Serbian Chemical Society ◽

10.2298/jsc100610113o ◽

2011 ◽

Vol 76 (9) ◽

pp. 1307-1323 ◽

Cited By ~ 4

Author(s):

Kosovka Obradovic-Djuricic ◽

Vesna Medic ◽

Marina Radisic ◽

Mila Lausevic

Keyword(s):

Triethylene Glycol ◽

Degree Of Conversion ◽

Cement Matrix ◽

Dental Resin ◽

Resin Cements ◽

Triethylene Glycol Dimethacrylate ◽

Urethane Dimethacrylate ◽

Post Hoc ◽

Composite Cements ◽

One Way Anova

This study examined the possible correlation between the degree of conversion (DC) and the amount of substances eluted from three commercial cured resin-based cements. The DC of the various resin-based cements was measured by Raman spectroscopy, while the quantity of unreacted monomers released from the cement matrix (triethylene glycol dimethacrylate, TEGDMA, urethane dimethacrylate, UDMA, 2- hydroxyethyl methacrylate, HEMA and bis phenol A) was determined by high pressure liquid chromatography (HPLC). The obtained results, after multiple statistical evaluation (one way ANOVA, LSD post hoc test), showed no significant differences in the DC values between the resin cements. On the contrary, the results of the HPLC analysis depicted statistically significant differences between the three materials with respect to the amount of leached monomers. In addition, no correlation between the DC and the amount of eluted substances from the tested cured composite cements was found.

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

International Journal of Molecular Sciences ◽

10.3390/ijms21072644 ◽

2020 ◽

Vol 21 (7) ◽

pp. 2644 ◽

Cited By ~ 5

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.

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DEGREE OF POLYMERIZATION OF DUAL CURE RESIN CEMENT MEASURED BY FTIR

Contemporary Materials ◽

10.7251/comen1801016m ◽

2018 ◽

Vol 9 (1) ◽

Author(s):

Aleksandra Maletin ◽

Dubravka Marković ◽

Isidora Nešković ◽

Branislava Petronijević ◽

Tanja Veljović ◽

...

Keyword(s):

Clinical Success ◽

Triethylene Glycol ◽

Mean Value ◽

Degree Of Polymerization ◽

Resin Cement ◽

Polymerization Reaction ◽

Dental Resin ◽

Triethylene Glycol Dimethacrylate ◽

High Degree

Introduction: The degree of polymerization of dental resin cement materi- als is very important for the longevity and quality of the clinical success of the restorative procedure. Insufficiently effective polymerization reaction of dental resin cement materials may result in adverse effects on the mechanical and adhesive performance of the material. It is believed that the proportion of triethylene glycol dimethacrylate (TEGDMA) mono- mers in the chemical structure of the material significantly influences the polymerization reaction. With the increase in TEGDMA, the degree of conversion of monomers into the polymer increases. Aim: The aim of this study has been to determine the degree of polymerization of dual cure dental resin cement. Material and methods: For the analysis of the degree of polymerization, Fourier transform infrared (FTIR) spectroscopy was used. 10 samples of dual cure resin based cement Variolink II were prepared in accordance with the manufacturer's instructions. Analysis was performed 24 hours after polymerization procedure. Results: Degree of polymerization of Variolink II resin based cement ranged from 69.2% to 98.7% with a mean value of 85.81%. Conclusion: Variolink II dual cure resin cement contains a significant percentage of TEGDMA which can be the cause of high degree of polymerization. The minimum accep- table percentage of the degree of polymerization of dental resin cement has not yet been established.

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

Journal of Composite Materials ◽

10.1177/0021998317729004 ◽

2017 ◽

Vol 52 (12) ◽

pp. 1579-1588 ◽

Cited By ~ 4

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.

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A Low-Viscosity BisGMA Derivative for Resin Composites: Synthesis, Characterization, and Evaluation of Its Rheological Properties

Materials ◽

10.3390/ma14020338 ◽

2021 ◽

Vol 14 (2) ◽

pp. 338

Author(s):

Ali Alrahlah ◽

Abdel-Basit Al-Odayni ◽

Haifa Fahad Al-Mutairi ◽

Bashaer Mousa Almousa ◽

Faisal S. Alsubaie ◽

...

Keyword(s):

Substantial Reduction ◽

Triethylene Glycol ◽

High Viscosity ◽

Resin Matrix ◽

Resonance Spectroscopy ◽

Dental Resin ◽

Triethylene Glycol Dimethacrylate ◽

Oh Groups ◽

Low Viscosity ◽

13C Nuclear Magnetic Resonance

This study aimed to synthesize new bisphenol A-glycidyl methacrylate (BisGMA) derivatives, targeting a reduction in its viscosity by substituting one of its OH groups, the leading cause of its high viscosity, with a chlorine atom. Hence, this monochloro-BisGMA (mCl-BisGMA) monomer was synthesized by Appel reaction procedure, and its structure was confirmed using Fourier transform infrared spectroscopy, 1H and 13C-nuclear magnetic resonance spectroscopy, and mass spectroscopy. The viscosity of mCl-BisGMA (8.3 Pa·s) was measured under rheometry conditions, and it was found to be more than 65-fold lower than that of BisGMA (566.1 Pa·s) at 25 °C. For the assessment of the viscosity changes of model resins in the presence of mCl-BisGMA, a series of resin matrices, in which, besides BisGMA, 50 wt % was triethylene glycol dimethacrylate, were prepared and evaluated at 20, 25, and 35 °C. Thus, BisGMA was incrementally replaced by 25% mCl-BisGMA to obtain TBC0, TBC25, TBC50, TBC75, and TBC100 blends. The viscosity decreased with temperature, and the mCl-BisGMA content in the resin mixture increased. The substantial reduction in the viscosity value of mCl-BisGMA compared with that of BisGMA may imply its potential use as a dental resin matrix, either alone or in combination with traditional monomers. However, the various properties of mCl-BisGMA-containing matrices should be evaluated.

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The Photoinitiators Used in Resin Based Dental Composite—A Review and Future Perspectives

Polymers ◽

10.3390/polym13030470 ◽

2021 ◽

Vol 13 (3) ◽

pp. 470

Author(s):

Andrea Kowalska ◽

Jerzy Sokolowski ◽

Kinga Bociong

Keyword(s):

Current Knowledge ◽

Biomechanical Properties ◽

Degree Of Conversion ◽

Dental Composite ◽

Polymerization Process ◽

Dental Composites ◽

Dental Resin ◽

Dental Resins ◽

Light Curing

The presented paper concerns current knowledge of commercial and alternative photoinitiator systems used in dentistry. It discusses alternative and commercial photoinitiators and focuses on mechanisms of polymerization process, in vitro measurement methods and factors influencing the degree of conversion and hardness of dental resins. PubMed, Academia.edu, Google Scholar, Elsevier, ResearchGate and Mendeley, analysis from 1985 to 2020 were searched electronically with appropriate keywords. Over 60 articles were chosen based on relevance to this review. Dental light-cured composites are the most common filling used in dentistry, but every photoinitiator system requires proper light-curing system with suitable spectrum of light. Alternation of photoinitiator might cause changing the values of biomechanical properties such as: degree of conversion, hardness, biocompatibility. This review contains comparison of biomechanical properties of dental composites including different photosensitizers among other: camphorquinone, phenanthrenequinone, benzophenone and 1-phenyl-1,2 propanedione, trimethylbenzoyl-diphenylphosphine oxide, benzoyl peroxide. The major aim of this article was to point out alternative photoinitiators which would compensate the disadvantages of camphorquinone such as: yellow staining or poor biocompatibility and also would have mechanical properties as satisfactory as camphorquinone. Research showed there is not an adequate photoinitiator which can be as sufficient as camphorquinone (CQ), but alternative photosensitizers like: benzoyl germanium or novel acylphosphine oxide photoinitiators used synergistically with CQ are able to improve aesthetic properties and degree of conversion of dental resin.

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Commercial Dental Composite: Determination of Reaction Advancement and Study of the Migration of Organic Compounds

Polymers and Polymer Composites ◽

10.1177/096739110501300302 ◽

2005 ◽

Vol 13 (3) ◽

pp. 223-234

Author(s):

C. Sanglar ◽

M. Defay ◽

H. Waton ◽

A. Bonhomme ◽

S. Alamercery ◽

...

Keyword(s):

Artificial Saliva ◽

Aqueous Media ◽

Dental Composite ◽

Dental Composites ◽

Hydrophilic Monomer ◽

Methacrylate Monomers ◽

Urethane Dimethacrylate ◽

Hydrolysis Of

This work on organic dental composites was undertaken to determine the role of residual reactive methacrylate functions at the end of the photopolymerization cycle, and to investigate the fate of the residual monomers and oligomers in organic (ethanol) and aqueous (water and artificial saliva) media. The results show that all the methacrylate monomers present in dentine migrate into ethanol (about 1% (w/w)). In aqueous media on the other hand, only the most hydrophilic monomer (UDMA) migrates (0.05% (w/w)) into water and 0.03% into artificial saliva (pH = 9). This desorption in the three media is accompanied by the hydrolysis of monomers, leading to the formation of monohydrolyzed urethane dimethacrylate (UDMA) and bis-phenyl glycidyl dimethacrylate (BISGMA); UDMA and BISGMA are completely hydrolyzed in artificial saliva. The alkalinity of the milieu apparently favours the hydrolysis of methacrylate functions.

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Studies on the dehydrogenative polymerizations of monolignol β-glycosides. Part 2: Horseradish peroxidase-catalyzed dehydrogenative polymerization of isoconiferin

Holzforschung ◽

10.1515/hf.2006.085 ◽

2006 ◽

Vol 60 (5) ◽

pp. 513-518 ◽

Cited By ~ 13

Author(s):

Yuki Tobimatsu ◽

Toshiyuki Takano ◽

Hiroshi Kamitakahara ◽

Fumiaki Nakatsubo

Keyword(s):

Horseradish Peroxidase ◽

Water Solubility ◽

Homogeneous System ◽

Degree Of Polymerization ◽

Coniferyl Alcohol ◽

Water Soluble ◽

Optimum Conditions ◽

Spectroscopic Analyses ◽

Dehydrogenation Polymer ◽

Dehydrogenative Polymerization

Abstract Dehydrogenative polymerization of isoconiferin (IC; coniferyl alcohol γ-O-β-D-glucopyranoside) catalyzed by horseradish peroxidase (HRP) was carried out. The polymerization of IC proceeded in a homogeneous system, resulting in a water-soluble dehydrogenation polymer (IC-DHP). The degree of polymerization (DP) of IC-DHP was significantly higher than that of a standard dehydrogenative polymer (CA-DHP) obtained from coniferyl alcohol (CA) in a heterogeneous system. Under optimum conditions, the DP of IC-DHP was 44 (M n=1.5×104), whereas that for CA-DHP was only 11 (M n=3.0×103, as acetate). Spectroscopic analyses confirmed that IC-DHP has a lignin-like structure containing D-glucose moieties attached to the lignin side-chains. The D-glucose unit introduced into γ-O position of CA essentially influenced the water solubility and molecular mass of the resulting DHP.

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