{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T14:06:35Z","timestamp":1788444395634,"version":"build-2803163510"},"reference-count":72,"publisher":"MDPI AG","issue":"23","license":[{"start":{"date-parts":[[2024,12,7]],"date-time":"2024-12-07T00:00:00Z","timestamp":1733529600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Materials"],"abstract":"<jats:p>Billions of patients struggle with dental diseases every year. These mainly comprise caries and related diseases. This results in an extremely high demand for innovative, polymer composite filling materials that meet a number of dental requirements. The aim of the study was to modify the light-cured composition of permanent dental fillings by changing the composition of the liquid organic matrix. New photoinitiators (DQ1-DQ5) based on a quinoline or quinoxaline skeleton and a co-initiator-(phenylthio)acetic acid (PhTAA) were used. In addition, monomers that have been traditionally used in dental materials were replaced by trimethylolpropane triacrylate (TMPTA). The neutral dental glass IDG functioned as an inorganic filler. The influence of the storage conditions of the developed composites in solutions simulating the natural oral environment during the consumption of different meals on sorption, solubility, and mass changes was assessed. For the tests, fifty-four cylindrical composite samples were prepared according to ISO 4049 guidelines and stored in different solutions. Distilled water, artificial saliva, heptane, 10% ethanol, and 3% acetic acid, as well as solutions containing pigments such as coffee, tea, red wine, and Coca-Cola, were used for the studies. The samples were stored in these solutions for 7, 14, 28, 35, 42, 49, 56, and 63 days at 37 \u00b0C. The sorption, solubility, and mass changes in the tested samples were determined, and the trend of these changes as a function of storage time was presented. The results were analyzed considering the nature of the solution used, i.e., aqueous, hydrophobic, and acidic. The properties evaluated changed in a different way, characteristic for each of the abovementioned solution groups. It was found that the type of solution simulating the natural environment of the oral cavity has the greatest influence on the sorption, solubility, and changes in the mass of the tested material.<\/jats:p>","DOI":"10.3390\/ma17236003","type":"journal-article","created":{"date-parts":[[2024,12,9]],"date-time":"2024-12-09T10:11:47Z","timestamp":1733739107000},"page":"6003","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Modification of Light-Cured Composition for Permanent Dental Fillings; Mass Stability of New Composites Containing Quinoline and Quinoxaline Derivatives in Solutions Simulating the Oral Cavity Environment"],"prefix":"10.3390","volume":"17","author":[{"given":"Ilona","family":"Pyszka","sequence":"first","affiliation":[{"name":"Faculty of Chemical Technology and Engineering, Bydgoszcz University of Science and Technology, 85-326 Bydgoszcz, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3406-5828","authenticated-orcid":false,"given":"Beata","family":"J\u0119drzejewska","sequence":"additional","affiliation":[{"name":"Faculty of Chemical Technology and Engineering, Bydgoszcz University of Science and Technology, 85-326 Bydgoszcz, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,12,7]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"380","DOI":"10.1177\/0022034517693566","article-title":"Global, Regional, and National Prevalence, Incidence, and Disability-Adjusted Life Years for Oral Conditions for 195 Countries, 1990\u20132015: A Systematic Analysis for the Global Burden of Diseases, Injuries, and Risk Factors","volume":"96","author":"Kassebaum","year":"2017","journal-title":"J. Dent. Res."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"250","DOI":"10.1177\/0022034513517901","article-title":"Scaffoldless Tissue-Engineered Dental Pulp Cell Constructs for Endodontic Therapy","volume":"93","author":"Ray","year":"2014","journal-title":"J. Dent. Res."},{"key":"ref_3","unstructured":"Sakaguchi, R.L., and Powers, J.M. (2012). Craig\u2019s Restorative Dental Materials. Elsevier eBook on VitalSource, Elsevier. [13th ed.]."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1177\/1758736014555246","article-title":"Comparative Study of Mechanical Properties of Dental Restorative Materials and Dental Hard Tissues in Compressive Loads","volume":"5","author":"Chun","year":"2014","journal-title":"J. Dent. Biomech."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"5897","DOI":"10.1016\/j.biomaterials.2009.07.027","article-title":"On the Nature of Biomaterials","volume":"30","author":"Williams","year":"2009","journal-title":"Biomaterials"},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Schmalz, G., and Arenholt-Bindslev, D. (2009). Determination of Biocompatibility. Biocompatibility of Dental Materials, Springer.","DOI":"10.1007\/978-3-540-77782-3_2"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"453","DOI":"10.1080\/01694243.2021.1924499","article-title":"Current Modifications of Dental Adhesive Systems for Composite Resin Restorations: A Review in Literature","volume":"36","author":"Dionysopoulos","year":"2022","journal-title":"J. Adhes. Sci. Technol."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"44","DOI":"10.1177\/08959374920060011601","article-title":"Dental Composites\/Glass Ionomers: The Materials","volume":"6","author":"Bowen","year":"1992","journal-title":"Adv. Dent. Res."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"302","DOI":"10.1177\/10454411950060040301","article-title":"Current Trends in Dental Composites","volume":"6","author":"Ferracane","year":"1995","journal-title":"Crit. Rev. Oral Biol. Med."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"535","DOI":"10.1016\/S0079-6700(01)00005-3","article-title":"New Developments of Polymeric Dental Composites","volume":"26","author":"Moszner","year":"2001","journal-title":"Prog. Polym. Sci."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"29","DOI":"10.1016\/j.dental.2010.10.020","article-title":"Resin Composite\u2014State of the Art","volume":"27","author":"Ferracane","year":"2011","journal-title":"Dent. Mater."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1001","DOI":"10.1016\/j.dental.2009.02.009","article-title":"Future Perspectives of Resin-Based Dental Materials","volume":"25","author":"Jandt","year":"2009","journal-title":"Dent. Mater."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1228","DOI":"10.3390\/ma3021228","article-title":"Review: Resin Composite Filling","volume":"3","author":"Chan","year":"2010","journal-title":"Materials"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"549","DOI":"10.1177\/0022034510363765","article-title":"Update on Dental Nanocomposites","volume":"89","author":"Chen","year":"2010","journal-title":"J. Dent. Res."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"97","DOI":"10.1111\/j.1600-0722.1997.tb00188.x","article-title":"Resin Composites in Dentistry: The Monomer Systems","volume":"105","author":"Peutzfeldt","year":"1997","journal-title":"Eur. J. Oral Sci."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"300","DOI":"10.1111\/j.1708-8240.2000.tb00239.x","article-title":"Curing Dental Resins and Composites by Photopolymerization","volume":"12","author":"STANSBURY","year":"2000","journal-title":"J. Esthet. Restor. Dent."},{"key":"ref_17","unstructured":"P\u0105czkowski, J., and Neckers, D.C. (2008). Photoinduced Electron Transfer Initiating Systems for Free-Radical Polymerization. Electron Transfer in Chemistry, Wiley."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"2371","DOI":"10.1002\/macp.200400218","article-title":"Reinvestigation of the Mechanism of the Free Radical Polymerization Photoinitiation Process by Camphorquinone\u2013Coinitiator Systems: New Results","volume":"205","author":"Pyszka","year":"2004","journal-title":"Macromol. Chem. Phys."},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Allen, N.S. (2010). Photochemistry and Photophysics of Polymer Materials, Wiley.","DOI":"10.1002\/9780470594179"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"600","DOI":"10.1016\/0032-3861(92)90738-I","article-title":"Photopolymerization Kinetics of Dimethacrylates Using the Camphorquinone\/Amine Initiator System","volume":"33","author":"Cook","year":"1992","journal-title":"Polymer"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"47","DOI":"10.1002\/(SICI)1522-9505(19980601)257:1<47::AID-APMC47>3.0.CO;2-Z","article-title":"Photocuring Kinetic Studies of New Dental Restorative Resins Based on Poly(Ethylene Glycol) Diacrylate and Tris[2-(Acryloyloxy)-Ethyl]Isocyanurate","volume":"257","author":"Nie","year":"1998","journal-title":"Angew. Makromol. Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"490","DOI":"10.1111\/j.1600-0722.1982.tb00767.x","article-title":"Factors Affecting the Quantity of Remaining Double Bonds in Restorative Resin Polymers","volume":"90","author":"ASMUSSEN","year":"1982","journal-title":"Eur. J. Oral Sci."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"317","DOI":"10.32383\/farmpol\/153049","article-title":"Bis-GMA Monomer Elution from Modern Resin-Based Composites\u2014Preliminary in Vitro Study","volume":"78","author":"Rogocka","year":"2022","journal-title":"Farm. Pol."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"199","DOI":"10.1016\/j.reprotox.2007.06.004","article-title":"In Vivo Effects of Bisphenol A in Laboratory Rodent Studies","volume":"24","author":"Richter","year":"2007","journal-title":"Reprod. Toxicol."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"298","DOI":"10.1289\/ehp.96104298","article-title":"Estrogenicity of Resin-Based Composites and Sealants Used in Dentistry","volume":"104","author":"Olea","year":"1996","journal-title":"Environ. Health Perspect."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"660","DOI":"10.1002\/jbm.a.20077","article-title":"Genotoxicity Assessment of Oxirane-Based Dental Monomers in Mammalian Cells","volume":"68A","author":"Kostoryz","year":"2004","journal-title":"J. Biomed. Mater. Res. A"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"12","DOI":"10.1016\/S0109-5641(03)00053-8","article-title":"Resin Composite Monomers Alter MTT and LDH Activity of Human Gingival Fibroblasts In Vitro","volume":"20","author":"Issa","year":"2004","journal-title":"Dent. Mater."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1335","DOI":"10.1016\/j.dental.2015.08.156","article-title":"Dental Composite Components Induce DNA-Damage and Altered Nuclear Morphology in Gingiva Fibroblasts","volume":"31","author":"Styllou","year":"2015","journal-title":"Dent. Mater."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"81","DOI":"10.1016\/S0022-3913(03)00178-1","article-title":"Monomer Permeability of Disposable Dental Gloves","volume":"90","author":"Nakamura","year":"2003","journal-title":"J. Prosthet. Dent."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"2202352","DOI":"10.1002\/admi.202202352","article-title":"The Blue-LED-Sensitive Naphthoquinone-Imidazolyl Derivatives as Type II Photoinitiators of Free Radical Photopolymerization","volume":"10","author":"Borjigin","year":"2023","journal-title":"Adv. Mater. Interfaces"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1313","DOI":"10.1016\/j.dental.2006.11.010","article-title":"Effect of Different Photoinitiator Systems on Conversion Profiles of a Model Unfilled Light-Cured Resin","volume":"23","author":"Schroeder","year":"2007","journal-title":"Dent. Mater."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1565","DOI":"10.1016\/j.jdent.2015.08.015","article-title":"Effect of Different Photoinitiators and Reducing Agents on Cure Efficiency and Color Stability of Resin-Based Composites Using Different LED Wavelengths","volume":"43","author":"Rocha","year":"2015","journal-title":"J. Dent."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"750","DOI":"10.1039\/b604149c","article-title":"Identification of Organic Extractables from Commercial Resin-Modified Glass-Ionomers Using HPLC-MS","volume":"8","author":"Rogalewicz","year":"2006","journal-title":"J. Environ. Monit."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"103894","DOI":"10.1016\/j.jdent.2021.103894","article-title":"Bisphenol A Release from Short-Term Degraded Resin-Based Dental Materials","volume":"116","author":"Duca","year":"2022","journal-title":"J. Dent."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1146","DOI":"10.1016\/j.dental.2012.08.006","article-title":"Correlation of the Degree of Conversion with the Amount of Elutable Substances in Nano-Hybrid Dental Composites","volume":"28","author":"Durner","year":"2012","journal-title":"Dent. Mater."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"211","DOI":"10.1016\/j.dental.2005.05.005","article-title":"Hygroscopic and Hydrolytic Effects in Dental Polymer Networks","volume":"22","author":"Ferracane","year":"2006","journal-title":"Dent. Mater."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"1003","DOI":"10.1016\/j.dental.2011.06.007","article-title":"Sorption of Water, Ethanol or Ethanol\/Water Solutions by Light-Cured Dental Dimethacrylate Resins","volume":"27","author":"Sideridou","year":"2011","journal-title":"Dent. Mater."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"e63","DOI":"10.1016\/j.dental.2012.03.011","article-title":"Water Sorption Characteristics of Restorative Dental Composites Immersed in Acidic Drinks","volume":"28","author":"Rahim","year":"2012","journal-title":"Dent. Mater."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"1106","DOI":"10.1046\/j.1365-2842.2001.00802.x","article-title":"Water Sorption and Solubility of Dental Composites and Identification of Monomers Released in an Aqueous Environment","volume":"28","author":"Wellendorf","year":"2001","journal-title":"J. Oral Rehabil."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"1187","DOI":"10.1016\/S0142-9612(99)00003-4","article-title":"Water Sorption, Solubility and Effect of Post-Curing of Glass Fibre Reinforced Polymers","volume":"20","author":"Miettinen","year":"1999","journal-title":"Biomaterials"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"1695","DOI":"10.1016\/j.biomaterials.2005.09.037","article-title":"Effect of Resin Hydrophilicity and Temperature on Water Sorption of Dental Adhesive Resins","volume":"27","author":"Yiu","year":"2006","journal-title":"Biomaterials"},{"key":"ref_42","doi-asserted-by":"crossref","unstructured":"Pyszka, I., and J\u0119drzejewska, B. (2024). Design of Dyes Based on the Quinoline or Quinoxaline Skeleton towards Visible Light Photoinitiators. Int. J. Mol. Sci., 25.","DOI":"10.3390\/ijms25084289"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"2115","DOI":"10.3390\/molecules20022115","article-title":"Synthesis, Crystal Structure, Spectroscopic Properties and Potential Biological Activities of Salicylate\u2013Neocuproine Ternary Copper(II) Complexes","volume":"20","author":"Valko","year":"2015","journal-title":"Molecules"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"40","DOI":"10.1016\/j.molstruc.2017.04.048","article-title":"New Mixed Ligand Cobalt(II\/III) Complexes Based on the Drug Sodium Valproate and Bioactive Nitrogen-Donor Ligands. Synthesis, Structure and Biological Properties","volume":"1142","author":"Kamel","year":"2017","journal-title":"J. Mol. Struct."},{"key":"ref_45","first-page":"504","article-title":"Synthesis, Characterization and Biological Studies of Co(II), Ni(II), Cu(II) and Zn(II) Complexes of Schiff Bases Derived from 3-Formyl-2-Mercaptoquinolines","volume":"3","author":"Dhumwad","year":"2011","journal-title":"J. Chem. Pharm. Res."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"214","DOI":"10.4236\/ijoc.2013.33029","article-title":"Synthesis of 5-Substituted 2, 9-Dimethyl-1,10-Phenanthroline Dialdehydes and Their Schiff Bases with Sulfur-Containing Amines","volume":"3","author":"Jaman","year":"2013","journal-title":"Int. J. Org. Chem."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"136","DOI":"10.1016\/j.ejmech.2018.11.059","article-title":"Antitumoral Activity of Quinoxaline Derivatives: A Systematic Review","volume":"163","author":"Montana","year":"2019","journal-title":"Eur. J. Med. Chem."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"249","DOI":"10.1016\/j.poly.2016.06.003","article-title":"New Zinc(II) Complexes of the Non-Steroidal Anti-Inflammatory Drug (Indomethacin) and Various Nitrogen Donor Ligands. Synthesis, Characterization and Biological Activity","volume":"117","author":"Jabali","year":"2016","journal-title":"Polyhedron"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"664","DOI":"10.1016\/j.ejmech.2014.06.058","article-title":"Quinoxaline, Its Derivatives and Applications: A State of the Art Review","volume":"97","author":"Pereira","year":"2015","journal-title":"Eur. J. Med. Chem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"269","DOI":"10.1021\/ma00105a036","article-title":"Generalization of the Kinetic Scheme for a Dye-Photosensitized Free-Radical Polymerization Initiating System via an Intermolecular Electron-Transfer Process. Application of Marcus Theory","volume":"28","author":"Paczkowski","year":"1995","journal-title":"Macromolecules"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"300","DOI":"10.1111\/jerd.12119","article-title":"Water Sorption, Solubility, and Color Stability of Giomer Restoratives","volume":"27","author":"Gonulol","year":"2015","journal-title":"J. Esthet. Restor. Dent."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"139","DOI":"10.4012\/dmj.27.139","article-title":"Color Stability of Different Denture Teeth Materials against Various Staining Agents","volume":"27","author":"KOKSAL","year":"2008","journal-title":"Dent. Mater. J."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"371","DOI":"10.4012\/dmj.25.371","article-title":"Color Stability of Resin Composites after Immersion in Different Drinks","volume":"25","author":"ERTAS","year":"2006","journal-title":"Dent. Mater. J."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"279","DOI":"10.1111\/jerd.12106","article-title":"Color Stability Over Time of Three Resin-Based Restorative Materials Stored Dry and in Artificial Saliva","volume":"26","author":"Uchimura","year":"2014","journal-title":"J. Esthet. Restor. Dent."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"70","DOI":"10.1016\/j.prosdent.2004.09.025","article-title":"Color Stability of Provisional Crown and Fixed Partial Denture Resins","volume":"93","author":"Haselton","year":"2005","journal-title":"J. Prosthet. Dent."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"533","DOI":"10.1016\/S0022-3913(98)70028-9","article-title":"Color Stability of Provisional Resin Restorative Materials","volume":"80","author":"Yannikakis","year":"1998","journal-title":"J. Prosthet. Dent."},{"key":"ref_57","unstructured":"(2019). Dentistry\u2014Polymer-Based Restorative Materials, Ed. 5 (Standard No. PN-EN ISO 4049:2019)."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"663","DOI":"10.1016\/j.dental.2003.08.008","article-title":"Physical and Mechanical Properties of an Experimental Dental Composite Based on a New Monomer","volume":"20","author":"Atai","year":"2004","journal-title":"Dent. Mater."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"197","DOI":"10.1016\/j.dental.2010.10.014","article-title":"Diffusion and Concurrent Solubility of Self-Adhering and New Resin\u2013Matrix Composites during Water Sorption\/Desorption Cycles","volume":"27","author":"Wei","year":"2011","journal-title":"Dent. Mater."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"39856","DOI":"10.1002\/app.39856","article-title":"Sorption, Solubility, and Mass Changes of Hydroxyapatite-Containing Composites in Artificial Saliva, Food Simulating Solutions, Tea, and Coffee","volume":"131","author":"Okulus","year":"2014","journal-title":"J. Appl. Polym. Sci."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"478","DOI":"10.1016\/S0109-5641(02)00093-3","article-title":"Hydrolytic Stability of Experimental Hydroxyapatite-Filled Dental Composite Materials","volume":"19","author":"Domingo","year":"2003","journal-title":"Dent. Mater."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"343","DOI":"10.1016\/S0142-9612(96)00124-X","article-title":"Water Sorption Characteristics of Resin-Modified Glass-Ionomer Cements","volume":"18","author":"Kanchanavasita","year":"1997","journal-title":"Biomaterials"},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"7739","DOI":"10.1016\/S0032-3861(01)00278-6","article-title":"Mechanical Characterization and Morphology of Carboxyl Randomized Poly(2-Ethyl Hexyl Acrylate) Liquid Rubber Toughened Epoxy Resins","volume":"42","author":"Ratna","year":"2001","journal-title":"Polymer"},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"1704486","DOI":"10.1002\/adma.201704486","article-title":"Synthetic Light-Curable Polymeric Materials Provide a Supportive Niche for Dental Pulp Stem Cells","volume":"30","author":"Vining","year":"2018","journal-title":"Adv. Mater."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"5506","DOI":"10.1021\/ma048569y","article-title":"UV-Induced Frontal Polymerization of Multifunctional (Meth)Acrylates","volume":"38","author":"Nason","year":"2005","journal-title":"Macromolecules"},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"747","DOI":"10.1177\/0022034517702620","article-title":"Randomized Clinical Trials on Deep Carious Lesions: 5-Year Follow-Up","volume":"96","author":"Fransson","year":"2017","journal-title":"J. Dent. Res."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"2542","DOI":"10.1002\/adma.201204936","article-title":"Discovery of Novel Materials with Broad Resistance to Bacterial Attachment Using Combinatorial Polymer Microarrays","volume":"25","author":"Hook","year":"2013","journal-title":"Adv. Mater."},{"key":"ref_68","first-page":"244","article-title":"Organotin (IV) Derivative of Piperic Acid and Phenylthioacetic Acid: Synthesis, Crystal Structure, Spectroscopic Characterizations and Biological Activities","volume":"8","author":"Dahmani","year":"2020","journal-title":"Moroc. J. Chem."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"225","DOI":"10.1007\/s10870-020-00847-0","article-title":"Synthesis, Characterization and Biological Activity of (Phenylthio)Acetic Acid:Theophylline Cocrystal","volume":"51","author":"Velmurugan","year":"2021","journal-title":"J. Chem. Crystallogr."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"367","DOI":"10.1016\/S0142-9612(03)00529-5","article-title":"Water Sorption Characteristics of Light-Cured Dental Resins and Composites Based on Bis-EMA\/PCDMA","volume":"25","author":"Sideridou","year":"2004","journal-title":"Biomaterials"},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"375","DOI":"10.1177\/0885328206064823","article-title":"Dental Composites Based on Amorphous Calcium Phosphate\u2014Resin Composition\/Physicochemical Properties Study","volume":"21","author":"Skrtic","year":"2007","journal-title":"J. Biomater. Appl."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"394","DOI":"10.1016\/S0109-5641(00)00097-X","article-title":"Water Sorption and Mechanical Behaviour of Cosmetic Direct Restorative Materials in Artificial Saliva","volume":"17","author":"Musanje","year":"2001","journal-title":"Dent. Mater."}],"container-title":["Materials"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1996-1944\/17\/23\/6003\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T16:49:29Z","timestamp":1760114969000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1996-1944\/17\/23\/6003"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,12,7]]},"references-count":72,"journal-issue":{"issue":"23","published-online":{"date-parts":[[2024,12]]}},"alternative-id":["ma17236003"],"URL":"https:\/\/doi.org\/10.3390\/ma17236003","relation":{},"ISSN":["1996-1944"],"issn-type":[{"value":"1996-1944","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,12,7]]}}}