Novel Urethane-Dimethacrylate Monomers and Compositions for Use as Matrices in Dental Restorative Materials
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 ob...
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| Format: | Article |
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MDPI AG
2020-04-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/21/7/2644 |
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| author | Izabela M. Barszczewska-Rybarek Marta W. Chrószcz Grzegorz Chladek |
| author_facet | Izabela M. Barszczewska-Rybarek Marta W. Chrószcz Grzegorz Chladek |
| author_sort | Izabela M. Barszczewska-Rybarek |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-10T20:32:57Z |
| format | Article |
| id | doaj.art-660faef15d53435b8a73bc66c152ce39 |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-10T20:32:57Z |
| publishDate | 2020-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-660faef15d53435b8a73bc66c152ce392023-11-19T21:15:03ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672020-04-01217264410.3390/ijms21072644Novel Urethane-Dimethacrylate Monomers and Compositions for Use as Matrices in Dental Restorative MaterialsIzabela M. Barszczewska-Rybarek0Marta W. Chrószcz1Grzegorz Chladek2Department of Physical Chemistry and Technology of Polymers, Silesian University of Technology, 44-100 Gliwice, PolandDepartment of Physical Chemistry and Technology of Polymers, Silesian University of Technology, 44-100 Gliwice, PolandInstitute of Engineering Materials and Biomaterials, Silesian University of Technology, 44-100 Gliwice, PolandIn 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.https://www.mdpi.com/1422-0067/21/7/2644dental restorative materialsurethane-dimethacrylatesdegree of conversionpolymerization shrinkagewater sorptionflexural properties |
| spellingShingle | Izabela M. Barszczewska-Rybarek Marta W. Chrószcz Grzegorz Chladek Novel Urethane-Dimethacrylate Monomers and Compositions for Use as Matrices in Dental Restorative Materials International Journal of Molecular Sciences dental restorative materials urethane-dimethacrylates degree of conversion polymerization shrinkage water sorption flexural properties |
| title | Novel Urethane-Dimethacrylate Monomers and Compositions for Use as Matrices in Dental Restorative Materials |
| title_full | Novel Urethane-Dimethacrylate Monomers and Compositions for Use as Matrices in Dental Restorative Materials |
| title_fullStr | Novel Urethane-Dimethacrylate Monomers and Compositions for Use as Matrices in Dental Restorative Materials |
| title_full_unstemmed | Novel Urethane-Dimethacrylate Monomers and Compositions for Use as Matrices in Dental Restorative Materials |
| title_short | Novel Urethane-Dimethacrylate Monomers and Compositions for Use as Matrices in Dental Restorative Materials |
| title_sort | novel urethane dimethacrylate monomers and compositions for use as matrices in dental restorative materials |
| topic | dental restorative materials urethane-dimethacrylates degree of conversion polymerization shrinkage water sorption flexural properties |
| url | https://www.mdpi.com/1422-0067/21/7/2644 |
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