Synthesis of chemically modified BisGMA analog with low viscosity and potential physical and biological properties for dental resin composite
The currently available commercial dental resin composites have limitations in use owing to the high viscosity and water sorption of Bisphenol A glycidyl methacrylate (BisGMA). The objective of this study was to obtain a BisGMA analog with reduced viscosity and hydrophilicity for potential use as an...
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| Veröffentlicht in: | Dental materials 2019-11, Vol.35 (11), p.1532-1544 |
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| creator | Al-Odayni, Abdel-Basit Alfotawi, Randa Khan, Rawaiz Sharaf Saeed, Waseem Al-Kahtani, Abdullah Aouak, Taieb Alrahlah, Ali |
| description | The currently available commercial dental resin composites have limitations in use owing to the high viscosity and water sorption of Bisphenol A glycidyl methacrylate (BisGMA). The objective of this study was to obtain a BisGMA analog with reduced viscosity and hydrophilicity for potential use as an alternative to BisGMA in dental resin composites.
The targeted chlorinated BisGMA (Cl-BisGMA) monomer was synthesized via the Appel reaction. The structural modification was confirmed via 1H- and 13C nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, and mass spectrometry. Five resin mixtures (70:30wt.%: F1=BisGMA/TEGDMA; F2=Cl-BisGMA/TEGDMA; F3=Cl-BisGMA only; F4=Cl-BisGMA/BisGMA; F5 contained 15% TEGDMA with equal amounts of BisGMA and Cl-BisGMA) were prepared. The viscosity, degree of double-bond conversion (DC), water sorption (WSP), and solubility (WSL) were tested. Cell viability and live/dead assays, as well as cell attachment and morphology assessments, were applied for cytotoxicity evaluation.
Cl-BisGMA was successfully synthesized with the viscosity reduced to 7.22 (Pas) compared to BisGMA (909.93,Pas). Interestingly, the DC of the F2 resin was the highest (70.6%). By the addition of equivalence concentration of Cl-BisGMA instead of BisGMA, the WSP was decreased from 2.95% (F1) to 0.41% (F2) with no significant change in WSL. However, the WSL increased with high Cl-BisGMA content. Biological tests revealed that all the resins were biocompatible during CL1 incubation.
The experimental resins based on Cl-BisGMA exhibited improved properties compared with the control samples, e.g., biocompatibility and lower viscosity, indicating that Cl-BisGMA can be considered as a potential monomer for application in dental resin composites. |
| doi_str_mv | 10.1016/j.dental.2019.07.013 |
| format | Article |
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The targeted chlorinated BisGMA (Cl-BisGMA) monomer was synthesized via the Appel reaction. The structural modification was confirmed via 1H- and 13C nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, and mass spectrometry. Five resin mixtures (70:30wt.%: F1=BisGMA/TEGDMA; F2=Cl-BisGMA/TEGDMA; F3=Cl-BisGMA only; F4=Cl-BisGMA/BisGMA; F5 contained 15% TEGDMA with equal amounts of BisGMA and Cl-BisGMA) were prepared. The viscosity, degree of double-bond conversion (DC), water sorption (WSP), and solubility (WSL) were tested. Cell viability and live/dead assays, as well as cell attachment and morphology assessments, were applied for cytotoxicity evaluation.
Cl-BisGMA was successfully synthesized with the viscosity reduced to 7.22 (Pas) compared to BisGMA (909.93,Pas). Interestingly, the DC of the F2 resin was the highest (70.6%). By the addition of equivalence concentration of Cl-BisGMA instead of BisGMA, the WSP was decreased from 2.95% (F1) to 0.41% (F2) with no significant change in WSL. However, the WSL increased with high Cl-BisGMA content. Biological tests revealed that all the resins were biocompatible during CL1 incubation.
The experimental resins based on Cl-BisGMA exhibited improved properties compared with the control samples, e.g., biocompatibility and lower viscosity, indicating that Cl-BisGMA can be considered as a potential monomer for application in dental resin composites.</description><identifier>ISSN: 0109-5641</identifier><identifier>EISSN: 1879-0097</identifier><identifier>DOI: 10.1016/j.dental.2019.07.013</identifier><identifier>PMID: 31421956</identifier><language>eng</language><publisher>England: Elsevier Inc</publisher><subject>Biocompatibility ; Biological properties ; BisGMA derivative ; Bisphenol A ; Bisphenol A glycidyl methacrylate ; Cell adhesion ; Cell viability ; Composite materials ; Composite Resins ; Cytology ; Cytotoxicity ; Dental cement ; Dental material ; Dental materials ; Dental resin composite ; Dental restorative materials ; Dentistry ; Fourier transforms ; Infrared spectroscopy ; Low viscosity ; Magnetic resonance spectroscopy ; Mass spectrometry ; Mass spectroscopy ; Materials Testing ; Methacrylates ; Morphology ; NMR ; Nuclear magnetic resonance ; Organic chemistry ; Phenols ; Polyethylene Glycols ; Polymer matrix composites ; Polymethacrylic Acids ; Resins ; Solubility ; Sorption ; Toxicity ; Triethylene glycol dimethacrylate ; Viscosity</subject><ispartof>Dental materials, 2019-11, Vol.35 (11), p.1532-1544</ispartof><rights>2019 The Academy of Dental Materials</rights><rights>Copyright © 2019 The Academy of Dental Materials. Published by Elsevier Inc. All rights reserved.</rights><rights>Copyright Elsevier BV Nov 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c305t-b2c516ba5bfb60432a822354143ab022c2e60c7b4c94a3b70ddfbc660f8b68fa3</citedby><cites>FETCH-LOGICAL-c305t-b2c516ba5bfb60432a822354143ab022c2e60c7b4c94a3b70ddfbc660f8b68fa3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S010956411930689X$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31421956$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Al-Odayni, Abdel-Basit</creatorcontrib><creatorcontrib>Alfotawi, Randa</creatorcontrib><creatorcontrib>Khan, Rawaiz</creatorcontrib><creatorcontrib>Sharaf Saeed, Waseem</creatorcontrib><creatorcontrib>Al-Kahtani, Abdullah</creatorcontrib><creatorcontrib>Aouak, Taieb</creatorcontrib><creatorcontrib>Alrahlah, Ali</creatorcontrib><title>Synthesis of chemically modified BisGMA analog with low viscosity and potential physical and biological properties for dental resin composite</title><title>Dental materials</title><addtitle>Dent Mater</addtitle><description>The currently available commercial dental resin composites have limitations in use owing to the high viscosity and water sorption of Bisphenol A glycidyl methacrylate (BisGMA). The objective of this study was to obtain a BisGMA analog with reduced viscosity and hydrophilicity for potential use as an alternative to BisGMA in dental resin composites.
The targeted chlorinated BisGMA (Cl-BisGMA) monomer was synthesized via the Appel reaction. The structural modification was confirmed via 1H- and 13C nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, and mass spectrometry. Five resin mixtures (70:30wt.%: F1=BisGMA/TEGDMA; F2=Cl-BisGMA/TEGDMA; F3=Cl-BisGMA only; F4=Cl-BisGMA/BisGMA; F5 contained 15% TEGDMA with equal amounts of BisGMA and Cl-BisGMA) were prepared. The viscosity, degree of double-bond conversion (DC), water sorption (WSP), and solubility (WSL) were tested. Cell viability and live/dead assays, as well as cell attachment and morphology assessments, were applied for cytotoxicity evaluation.
Cl-BisGMA was successfully synthesized with the viscosity reduced to 7.22 (Pas) compared to BisGMA (909.93,Pas). Interestingly, the DC of the F2 resin was the highest (70.6%). By the addition of equivalence concentration of Cl-BisGMA instead of BisGMA, the WSP was decreased from 2.95% (F1) to 0.41% (F2) with no significant change in WSL. However, the WSL increased with high Cl-BisGMA content. Biological tests revealed that all the resins were biocompatible during CL1 incubation.
The experimental resins based on Cl-BisGMA exhibited improved properties compared with the control samples, e.g., biocompatibility and lower viscosity, indicating that Cl-BisGMA can be considered as a potential monomer for application in dental resin composites.</description><subject>Biocompatibility</subject><subject>Biological properties</subject><subject>BisGMA derivative</subject><subject>Bisphenol A</subject><subject>Bisphenol A glycidyl methacrylate</subject><subject>Cell adhesion</subject><subject>Cell viability</subject><subject>Composite materials</subject><subject>Composite Resins</subject><subject>Cytology</subject><subject>Cytotoxicity</subject><subject>Dental cement</subject><subject>Dental material</subject><subject>Dental materials</subject><subject>Dental resin composite</subject><subject>Dental restorative materials</subject><subject>Dentistry</subject><subject>Fourier transforms</subject><subject>Infrared spectroscopy</subject><subject>Low viscosity</subject><subject>Magnetic resonance spectroscopy</subject><subject>Mass spectrometry</subject><subject>Mass spectroscopy</subject><subject>Materials Testing</subject><subject>Methacrylates</subject><subject>Morphology</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Organic chemistry</subject><subject>Phenols</subject><subject>Polyethylene Glycols</subject><subject>Polymer matrix composites</subject><subject>Polymethacrylic Acids</subject><subject>Resins</subject><subject>Solubility</subject><subject>Sorption</subject><subject>Toxicity</subject><subject>Triethylene glycol dimethacrylate</subject><subject>Viscosity</subject><issn>0109-5641</issn><issn>1879-0097</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9UcFu1DAUtBCIbhf-ACFLXLgkPDuOvbkgtRW0SEUcgLNlOy-sV0kc7GyrfAT_jLcpHDhwsmzPzJs3Q8grBiUDJt8dyhbH2fQlB9aUoEpg1ROyYTvVFACNeko2wKApainYGTlP6QAAgjfsOTmrmOCsqeWG_Pq6jPMek080dNTtcfDO9P1Ch9D6zmNLL326_nxBzWj68IPe-3lP-3BP73xyIfl5yT8tncKczXjT02m_pJPEw7P1IZMerlMME8bZY6JdiHT1TmOePFIXhumkhS_Is870CV8-nlvy_eOHb1c3xe2X609XF7eFq6CeC8tdzaQ1te2sBFFxs-O8qgUTlbHAueMowSkrXCNMZRW0bWedlNDtrNx1ptqSt6tudvXziGnWQ14H-96MGI5Jc67qpuZCiAx98w_0EI4xh5FRFZNKCZWD3xKxolwMKUXs9BT9YOKiGehTXfqg15X1qS4NSmdWpr1-FD_aAdu_pD_9ZMD7FYA5jTuPUSfncXTY-ohu1m3w_5_wG-yAqow</recordid><startdate>201911</startdate><enddate>201911</enddate><creator>Al-Odayni, Abdel-Basit</creator><creator>Alfotawi, Randa</creator><creator>Khan, Rawaiz</creator><creator>Sharaf Saeed, Waseem</creator><creator>Al-Kahtani, Abdullah</creator><creator>Aouak, Taieb</creator><creator>Alrahlah, Ali</creator><general>Elsevier Inc</general><general>Elsevier BV</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QF</scope><scope>7QO</scope><scope>7QP</scope><scope>7QQ</scope><scope>7SC</scope><scope>7SE</scope><scope>7SP</scope><scope>7SR</scope><scope>7TA</scope><scope>7TB</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>F28</scope><scope>FR3</scope><scope>H8D</scope><scope>H8G</scope><scope>JG9</scope><scope>JQ2</scope><scope>K9.</scope><scope>KR7</scope><scope>L7M</scope><scope>L~C</scope><scope>L~D</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>201911</creationdate><title>Synthesis of chemically modified BisGMA analog with low viscosity and potential physical and biological properties for dental resin composite</title><author>Al-Odayni, Abdel-Basit ; Alfotawi, Randa ; Khan, Rawaiz ; Sharaf Saeed, Waseem ; Al-Kahtani, Abdullah ; Aouak, Taieb ; Alrahlah, Ali</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c305t-b2c516ba5bfb60432a822354143ab022c2e60c7b4c94a3b70ddfbc660f8b68fa3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Biocompatibility</topic><topic>Biological properties</topic><topic>BisGMA derivative</topic><topic>Bisphenol A</topic><topic>Bisphenol A glycidyl methacrylate</topic><topic>Cell adhesion</topic><topic>Cell viability</topic><topic>Composite materials</topic><topic>Composite Resins</topic><topic>Cytology</topic><topic>Cytotoxicity</topic><topic>Dental cement</topic><topic>Dental material</topic><topic>Dental materials</topic><topic>Dental resin composite</topic><topic>Dental restorative materials</topic><topic>Dentistry</topic><topic>Fourier transforms</topic><topic>Infrared spectroscopy</topic><topic>Low viscosity</topic><topic>Magnetic resonance spectroscopy</topic><topic>Mass spectrometry</topic><topic>Mass spectroscopy</topic><topic>Materials Testing</topic><topic>Methacrylates</topic><topic>Morphology</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Organic chemistry</topic><topic>Phenols</topic><topic>Polyethylene Glycols</topic><topic>Polymer matrix composites</topic><topic>Polymethacrylic Acids</topic><topic>Resins</topic><topic>Solubility</topic><topic>Sorption</topic><topic>Toxicity</topic><topic>Triethylene glycol dimethacrylate</topic><topic>Viscosity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Al-Odayni, Abdel-Basit</creatorcontrib><creatorcontrib>Alfotawi, Randa</creatorcontrib><creatorcontrib>Khan, Rawaiz</creatorcontrib><creatorcontrib>Sharaf Saeed, Waseem</creatorcontrib><creatorcontrib>Al-Kahtani, Abdullah</creatorcontrib><creatorcontrib>Aouak, Taieb</creatorcontrib><creatorcontrib>Alrahlah, Ali</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Aluminium Industry Abstracts</collection><collection>Biotechnology Research Abstracts</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Ceramic Abstracts</collection><collection>Computer and Information Systems Abstracts</collection><collection>Corrosion Abstracts</collection><collection>Electronics & Communications Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>Materials Business File</collection><collection>Mechanical & Transportation Engineering Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>ANTE: Abstracts in New Technology & Engineering</collection><collection>Engineering Research Database</collection><collection>Aerospace Database</collection><collection>Copper Technical Reference Library</collection><collection>Materials Research Database</collection><collection>ProQuest Computer Science Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Civil Engineering Abstracts</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Computer and Information Systems Abstracts Academic</collection><collection>Computer and Information Systems Abstracts Professional</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Dental materials</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Al-Odayni, Abdel-Basit</au><au>Alfotawi, Randa</au><au>Khan, Rawaiz</au><au>Sharaf Saeed, Waseem</au><au>Al-Kahtani, Abdullah</au><au>Aouak, Taieb</au><au>Alrahlah, Ali</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of chemically modified BisGMA analog with low viscosity and potential physical and biological properties for dental resin composite</atitle><jtitle>Dental materials</jtitle><addtitle>Dent Mater</addtitle><date>2019-11</date><risdate>2019</risdate><volume>35</volume><issue>11</issue><spage>1532</spage><epage>1544</epage><pages>1532-1544</pages><issn>0109-5641</issn><eissn>1879-0097</eissn><abstract>The currently available commercial dental resin composites have limitations in use owing to the high viscosity and water sorption of Bisphenol A glycidyl methacrylate (BisGMA). The objective of this study was to obtain a BisGMA analog with reduced viscosity and hydrophilicity for potential use as an alternative to BisGMA in dental resin composites.
The targeted chlorinated BisGMA (Cl-BisGMA) monomer was synthesized via the Appel reaction. The structural modification was confirmed via 1H- and 13C nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, and mass spectrometry. Five resin mixtures (70:30wt.%: F1=BisGMA/TEGDMA; F2=Cl-BisGMA/TEGDMA; F3=Cl-BisGMA only; F4=Cl-BisGMA/BisGMA; F5 contained 15% TEGDMA with equal amounts of BisGMA and Cl-BisGMA) were prepared. The viscosity, degree of double-bond conversion (DC), water sorption (WSP), and solubility (WSL) were tested. Cell viability and live/dead assays, as well as cell attachment and morphology assessments, were applied for cytotoxicity evaluation.
Cl-BisGMA was successfully synthesized with the viscosity reduced to 7.22 (Pas) compared to BisGMA (909.93,Pas). Interestingly, the DC of the F2 resin was the highest (70.6%). By the addition of equivalence concentration of Cl-BisGMA instead of BisGMA, the WSP was decreased from 2.95% (F1) to 0.41% (F2) with no significant change in WSL. However, the WSL increased with high Cl-BisGMA content. Biological tests revealed that all the resins were biocompatible during CL1 incubation.
The experimental resins based on Cl-BisGMA exhibited improved properties compared with the control samples, e.g., biocompatibility and lower viscosity, indicating that Cl-BisGMA can be considered as a potential monomer for application in dental resin composites.</abstract><cop>England</cop><pub>Elsevier Inc</pub><pmid>31421956</pmid><doi>10.1016/j.dental.2019.07.013</doi><tpages>13</tpages></addata></record> |
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| ispartof | Dental materials, 2019-11, Vol.35 (11), p.1532-1544 |
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| subjects | Biocompatibility Biological properties BisGMA derivative Bisphenol A Bisphenol A glycidyl methacrylate Cell adhesion Cell viability Composite materials Composite Resins Cytology Cytotoxicity Dental cement Dental material Dental materials Dental resin composite Dental restorative materials Dentistry Fourier transforms Infrared spectroscopy Low viscosity Magnetic resonance spectroscopy Mass spectrometry Mass spectroscopy Materials Testing Methacrylates Morphology NMR Nuclear magnetic resonance Organic chemistry Phenols Polyethylene Glycols Polymer matrix composites Polymethacrylic Acids Resins Solubility Sorption Toxicity Triethylene glycol dimethacrylate Viscosity |
| title | Synthesis of chemically modified BisGMA analog with low viscosity and potential physical and biological properties for dental resin composite |
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