Increasing the environmental impact and biocompatibility of poly(bis-GMA) dental resin using crosslinking with amended cellulose

Increasing the environmental impact and biocompatibility of poly(bis-GMA) dental resin using crosslinking with amended cellulose | Research Square window.SnipcartSettings = { analytics: { enabled: false } }; (function() { var accessVector = localStorage.getItem('access_vector') || ''; window.dataLayer = window.dataLayer || []; if (accessVector) { window.dataLayer.push({ user: { profile: { profileInfo: { snid: accessVector } } } }); } })(); (function(w,d,s,l,i){w[l]=w[l]||[];w[l].push({'gtm.start':new Date().getTime(),event:'gtm.js'});var f=d.getElementsByTagName(s)[0],j=d.createElement(s),dl=l!='dataLayer'?'&l='+l:'';j.async=true;j.src='https://www.googletagmanager.com/gtm.js?id='+i+dl;f.parentNode.insertBefore(j,f);})(window,document,'script','dataLayer','GTM-K279D39R'); Browse Preprints In Review Journals COVID-19 Preprints AJE Video Bytes Research Tools Research Promotion AJE Professional Editing AJE Rubriq About Preprint Platform In Review Editorial Policies Our Team Advisory Board Help Center Sign In Submit a Preprint Cite Share Download PDF Research Article Increasing the environmental impact and biocompatibility of poly(bis-GMA) dental resin using crosslinking with amended cellulose Mehdi Khalaj, Maryam Bakhtiy, Seyed Jalal Hoseyni, Seyed Mahmoud Musavi, and 1 more This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-6378059/v1 This work is licensed under a CC BY 4.0 License Status: Posted Version 1 posted You are reading this latest preprint version Abstract This study investigates the synthesis and characterization of crosslinked poly(Bis-GMA) with cellulose using a chemical modification approach. The preparation involves three key steps: polymerization of bisphenol A glycidyl methacrylate (Bis-GMA), chlorination of poly(Bis-GMA), and crosslinking with cellulose. The resulting materials were characterized using CHN analysis, FT-IR, TGA-DTA, and mechanical testing. CHN analysis revealed changes in elemental composition due to chlorination and cellulose incorporation. At the same time, FT-IR confirmed successful chemical modifications, with the formation of new functional groups such as N-H and C-O bonds. TGA-DTA analysis indicated a decrease in thermal stability after crosslinking, with crosslinked poly(Bis-GMA) with cellulose decomposing at a lower temperature than Bis-GMA. Mechanical testing showed enhanced properties in the crosslinked material, with improved flexural strength, flexural modulus, diametral tensile strength, and compressive strength, likely due to the reinforcing effect of cellulose. Water adsorption studies highlighted the hydrophilic nature of cellulose, leading to increased water uptake in the crosslinked material. These findings suggest that cellulose-crosslinked poly(bis-GMA) offers improved mechanical properties and could be a promising material for applications in dental composites, biomedical coatings, and other polymer-based systems, though further modifications may be necessary to address water stability issues. Biocompatibility poly(Bis-GMA) dental resin cellulose crosslinked polymers Figures Figure 1 Figure 2 Figure 3 Figure 4 Introduction Dental restorative materials based on bisphenol A glycidyl methacrylate (Bis-GMA) have been widely utilized due to their superior mechanical properties, aesthetic advantages, and ease of application. However, their environmental impact and biocompatibility have been subjects of growing concern (Cho et al. 2022 ). Bis-GMA-based resins have been reported to release residual monomers, including bisphenol A (BPA), which has potential estrogenic effects and cytotoxicity, raising concerns about their long-term safety for both patients and dental practitioners. Additionally, conventional polymerization techniques often result in the incomplete conversion of monomers to polymer, leading to compromised mechanical stability and the potential for degradation over time (Cho et al. 2022 , Leisch et al. 2010 ). To overcome the limitations of traditional dental composites, recent research has emphasized the integration of bio-based materials to enhance biocompatibility, mechanical resilience, and sustainability (Andrew et al. 2022). Conventional methacrylate-based monomers, commonly used in dental formulations, undergo radical polymerization to create durable crosslinked structures. However, this process often yields inconsistent polymer networks, leading to undesirable properties such as polymerization shrinkage, water sorption, and high internal stress (Aminoroaya et al. 2021 ). Furthermore, highly viscous monomers, such as Bis-GMA, hinder efficient filler incorporation and reduce overall workability. To address these challenges, researchers have developed bio-derived methacrylate monomers with improved characteristics. High-molecular-weight bio-based monomers have been synthesized to reduce shrinkage strain and enhance structural stability. Some of these features include bulky aliphatic or aromatic ring systems, which contribute to reduced stress development while maintaining optimal mechanical performance (Aminoroaya et al. 2021 , Pfeifer et al. 2011 , Inagaki et al. 2016 , Łukaszczyk et al. 2013 ). Additionally, alternatives to triethylene glycol dimethacrylate (TEGDMA), a commonly used diluent known for its cytotoxic potential and polymerization shrinkage, have been explored. Bio-based low-viscosity monomers such as acetyloxypropylene dimethacrylate (Acet-GDMA), ethoxylated isosorbide dimethacrylate (ISETMDA), and poly(propylene glycol) dimethacrylate (PPGDMA) offer reduced shrinkage and improved biocompatibility while preserving mechanical integrity. Another critical research direction focuses on replacing Bis-GMA to minimize exposure to bisphenol-A derivatives. Bio-derived monomers based on isosorbide have demonstrated lower toxicity while maintaining a balance between rigidity and flexibility, ensuring comparable or superior mechanical properties. Structural modifications of Bis-GMA itself have also yielded promising results, with novel derivatives exhibiting reduced water uptake, enhanced hydrophobicity, and minimized shrinkage. By integrating these bio-based alternatives, dental composites can achieve better performance, increased longevity, and reduced environmental impact, marking a significant step toward safer and more sustainable restorative materials (He et al. 2012 , Gonçalves et al. 2008 , Nie et al. 2001 , Huang et al. 2018 , Schoerpf et al. 2019 , Ligon-Auer et al. 2016 , Nguyen et al. 2018 , Podgórski 2010 , Walters et al. 2016 , Berlanga Duarte et al. 2017 ). Among the promising strategies is the integration of modified cellulose as a crosslinking agent in poly(Bis-GMA) resins. Cellulose, a naturally abundant and renewable biopolymer, possesses high mechanical strength, excellent biocompatibility, and the ability to form hydrogen bonds, which can significantly improve polymer network formation. Recent advancements in cellulose modification techniques, such as surface functionalization and nanoparticle incorporation, have demonstrated their potential to enhance the mechanical, thermal, and biological performance of dental materials (Carolin et al. 2023 , Seddiqi et al. 2021 ). By leveraging cellulose’s unique properties, crosslinking Bis-GMA with modified cellulose can lead to improved polymerization efficiency, reduced monomer release, and enhanced biodegradability, thereby addressing both the biocompatibility and environmental concerns associated with traditional dental resins. This approach aligns with the global movement toward sustainable dentistry, which seeks to minimize the ecological footprint of dental materials while ensuring patient safety and optimal clinical performance. Further exploration of cellulose-based crosslinking mechanisms, along with their impact on the physicochemical properties of Bis-GMA composites, is critical for the next generation of high-performance dental resins. This work aimed to synthesize and characterize crosslinked poly(Bis-GMA) with cellulose using a chemical modification approach. The study focused on enhancing the properties of poly(Bis-GMA) by incorporating cellulose into the polymer network to improve its mechanical performance, hydrophilicity, and biodegradability. The modification process involved three key steps: polymerization of Bis-GMA, chlorination of poly(Bis-GMA), and crosslinking with cellulose. Through various analytical techniques, including CHN analysis, FT-IR, TGA-DTA, and mechanical testing, the study explored the resulting crosslinked material's structural, thermal, and mechanical properties. Experimental 2.1. Reagents and Instrumentation: All solvents, reagents, and specific chemicals from Merck and Sigma-Aldrich companies were purchased from commercial suppliers. he Shimadzu TGA-DTG-60H instrument was used to measure the thermal behavior of the samples . The Bruker IR spectrophotometer was used for the FT-IR analysis on a KBr disk between 400 to 4000 cm -1 . 2.2.Synthesis of Poly(bis-GMA) In a 500 mL balloon equipped with a condenser, 50g of 4,4′-Isopropylidenediphenol dimethacrylate (bis-GMA, Sigma-Aldrich, 98%) was dissolved in toluene and mixed with 0.3 wt.% of 2,2′-azobis(2-methylpropionitrile) (AIBN; Sigma-Aldrich, ≥98.0%). The mixture was stirred at 80°C under a nitrogen atmosphere overnight. The resulting polymer was then dried, ground into a fine powder, and sieved to obtain homogeneous particles. Specimens with diameters of 3 mm and 6 mm were prepared. The samples were then subjected to thermal curing at 120°C for 2 hours. Afterward, the edges of the samples were smoothed using sandpaper. Mechanical tests were conducted using a universal testing machine (Instron 6025) at a speed of 10 mm/min with a force of 100 kN. The diametral tensile strength (DTS) test followed ADA Standard No. 27, while flexural strength (FS), flexural modulus (FM), and compressive strength (CS) measurements adhered to ISO 10477:92 standards. Statistical analysis was performed using ANOVA in Minitab software (p < 0.05). Tukey’s test was used for homogenous data, while the Dunnett post hoc test was applied to analyze non-homogeneous data. Each experiment was repeated three times to ensure accuracy and reliability. 2.3. Water Absorption Analysis The water absorption properties of the samples were evaluated using specimens measuring 10×10×4 mm 3 under ambient conditions. Before testing, all samples were thoroughly dried, and their initial weights were recorded. Each experiment was conducted in triplicate to ensure reliability. A precision digital balance (Denver, model: AA-200, USA) was used for weighing. The samples were then immersed in sealed containers holding 30 mL of distilled water with a neutral pH (pH = 7) at a constant temperature of 25°C. To monitor the absorption process, the samples were periodically taken out, their surfaces were carefully dried, and they were weighed before being placed back into the water. This procedure was repeated until no further weight change was observed, indicating equilibrium moisture content. Each test was performed three times for consistency. The percentage of water absorption was determined using the following formula: Water Absorption (%)=(W t −W i )/W i ×100 where W i represents the initial weight of the sample, and W t denotes its weight at a given time t [20]. Results and discussion 3.1 Characterization of Crosslinked poly(Bis-GMA) with cellulose This study employed a chemical modification approach to synthesize crosslinked poly(bis-GMA) with cellulose, as illustrated in Scheme 1. The preparation process involved three key steps: first, the polymerization of bis-GMA to form the base polymer; second, the chlorination of poly(bis-GMA) to introduce reactive sites; and finally, the crosslinking reaction with cellulose to enhance structural integrity and functionality. The introduction of cellulose into the polymer network likely improves mechanical properties, hydrophilicity, and biodegradability, making the modified material potentially suitable for various applications, such as biomedical coatings, dental composites, and sustainable polymeric materials. Further characterization of the crosslinked structure would provide deeper insights into the extent of modification and its impact on the material’s thermal and mechanical performance. The elemental composition of the prepared polymers was assessed through CHN analysis, as presented in Table 1. Poly(bis-GMA) exhibited a carbon content of 67.94%, hydrogen content of 7.08%, and negligible nitrogen content (0.01%). The introduction of chlorine in poly(chlorinated bis-GMA) led to a reduction in carbon (63.15%) and hydrogen (6.58%), which is consistent with the replacement of hydrogen atoms by chlorine, contributing to an increase in overall molecular weight. In contrast, crosslinking poly(bis-GMA) with cellulose resulted in a slight reduction in carbon content (64.87%) and an increase in hydrogen (7.62%) and nitrogen (0.06%). The presence of nitrogen suggests the incorporation of cellulose-derived moieties, potentially due to residual amines from the initial source. The increased hydrogen content aligns with the hydroxyl-rich structure of cellulose, which introduces additional hydrogen-bearing functional groups into the polymer network. Table 1: CHN analysis of prepared samples Polymer %C %H %N Poly (bis-GMA) 67.94 7.08 0.01 Poly (chlorinated bis-GMA) 63.15 6.58 0.01 Crosslinked poly(bis-GMA) with cellulose 64.87 7.62 0.06 FT-IR spectra (Figure 1) provide further confirmation of chemical modifications. In poly(chlorinated bis-GMA), a characteristic C-Cl stretching band appears at approximately 700–800 cm -1 , confirming the presence of chlorine atoms. The FT-IR spectrum of crosslinked poly(bis-GMA) with cellulose reveals significant structural modifications, confirming successful crosslinking and interaction between the two components. The appearance of a broad absorption peak at 3701 cm -1 , associated with N-H stretching, suggests the formation of new amine groups, while peaks at 3032 cm -1 (=C-H, sp 2 ) and 2884 cm -1 (C-H, sp 3 ) indicate the retention of both aromatic and aliphatic C-H bonds. The presence of C=C stretching vibrations at 1625 and 1575 cm -1 implies benzene rings within the polymer matrix. Additionally, peaks at 1091, 1151, and 1217 cm -1 correspond to C-O, C-N, and C-C bonds. The peak at 1729 cm -1 is due to the presence of ester groups. These spectral changes confirm a successful modification, with strong intermolecular bonding that could influence the material's mechanical and thermal properties. The thermal behavior and stability of bis-GMA and crosslinked poly(bis-GMA) with cellulose were assessed using TGA-DTA analysis, revealing a one-step decomposition process primarily associated with the degradation of the organic polymer chain. An initial weight loss of approximately 2% is observed, corresponding to the removal of adsorbed water and impurities, likely due to the hydrophobic nature of hydroxyl groups in the polymer structure. The main decomposition phase occurs between 350°C and 420°C (Figure 2), indicating the breakdown of the organic backbone, with DTA confirming that this process is exothermic. Notably, the decomposition temperature differs between the two materials, with bis-GMA decomposing at approximately 468°C, whereas the crosslinked poly(bis-GMA) with cellulose decomposes at a lower temperature of 398°C. The reduction in thermal stability after crosslinking suggests that the incorporation of cellulose alters the polymer network, potentially introducing weaker bonds or increasing structural heterogeneity. However, the exothermic nature of degradation indicates that energy is released during polymer breakdown, which is characteristic of crosslinked systems. These findings provide insight into the thermal stability of the material, which could be further explored for applications requiring controlled thermal degradation, such as biomedical, coating, or composite applications. The mechanical performance of poly(bis-GMA), poly(chlorinated bis-GMA), and crosslinked poly(bis-GMA) with cellulose was assessed based on flexural strength (FS), flexural modulus (FM), diametral tensile strength (DTS), and compressive strength (CS), as presented in Table 2. Poly(bis-GMA) exhibited moderate mechanical properties, with FS of 106.3 MPa, FM of 3.97 GPa, DTS of 24.5 MPa, and CS of 153.2 MPa. Chlorination of bis-GMA resulted in a notable decline in all mechanical parameters, with FS decreasing to 94.4 MPa, FM to 3.19 GPa, DTS to 19.8 MPa, and CS to 139.8 MPa. The reduction in mechanical properties may be attributed to the altered polymer network due to chlorine incorporation, potentially introducing structural defects or reducing crosslink density. In contrast, crosslinking bis-GMA with cellulose significantly enhanced all mechanical properties. The FS increased to 123.36 MPa, FM to 4.67 GPa, DTS to 31.5 MPa, and CS to 186.3 MPa, demonstrating improved load-bearing capacity and fracture resistance. The incorporation of cellulose likely contributed to this enhancement by reinforcing the polymer matrix, increasing rigidity, and improving stress distribution. These findings suggest that cellulose crosslinking effectively strengthens poly(bis-GMA) and could be a promising strategy for improving the mechanical performance of dental resins. Table 2: Mechanical properties Polymer FS [MPa] FM [GPa] DTS [MPa] CS [MPa] Poly (bis-GMA) 106.3 3.97 24.5 153.2 Poly (chlorinated bis-GMA) 94.4 3.19 19.8 139.8 Crosslinked poly(bis-GMA) with cellulose 123.36 4.67 31.5 186.3 3.2. Water Adsorption Water adsorption behavior was evaluated over 64 hours, as shown in Figure 3. Poly(bis-GMA) demonstrated a gradual increase in water adsorption, reaching 4.39% at 64 hours. Chlorination of bis-GMA led to a substantial reduction in water uptake, with adsorption values stabilizing at 1.93% at 64 hours. This reduction may be due to the increased hydrophobicity of the polymer following chlorine substitution, limiting water penetration into the polymer matrix. Conversely, crosslinked poly(bis-GMA) with cellulose exhibited the highest water adsorption, reaching 20.18% at 64 hours. The significant increase in water uptake can be attributed to the hydrophilic nature of cellulose, which contains hydroxyl groups capable of forming hydrogen bonds with water molecules. Although cellulose reinforcement enhanced mechanical properties, the increased water adsorption may raise concerns about long-term stability and degradation in aqueous environments. Future modifications, such as surface treatments or hybrid crosslinking strategies, could help mitigate excessive water uptake while maintaining the mechanical advantages provided by cellulose reinforcement. 3.3. CO 2 adsorption-desorption studies The CO 2 adsorption capacity of crosslinked poly(bis-GMA) with cellulose was measured using the mass-increasing method, with the results detailed in Figure 4. The functional groups present, such as NH and OH, were key in enhancing the adsorbent's efficiency in capturing CO 2 gas. The adsorption-desorption process was conducted in three stages. Initially, the sample was degassed at 145°C under N 2 gas flow, then cooled to 45°C and purged with N 2 for 30 minutes. The CO 2 adsorption phase followed, using a CO 2 /N 2 mixture (30% CO 2 ) at a flow rate of 60 mL/min. In the final stage, CO 2 desorption was facilitated by passing N 2 over the sample at a reduced temperature of 10°C/min, aiding the release of CO 2 from the material's surface. The data showed that crosslinked poly(bis-GMA) with cellulose could adsorb up to 403 mg of CO 2 per gram of adsorbent, indicating substantial adsorption potential Conclusion In this study, crosslinked poly(bis-GMA) with cellulose was successfully synthesized through a three-step chemical modification process involving polymerization, chlorination, and crosslinking. The incorporation of cellulose into the poly(bis-GMA) network significantly enhanced the material's mechanical properties, as evidenced by increased flexural strength, flexural modulus, diametral tensile strength, and compressive strength. FT-IR analysis confirmed the formation of new functional groups, while TGA-DTA analysis revealed that crosslinking with cellulose reduces thermal stability, suggesting structural changes in the polymer matrix. Water adsorption studies indicated that cellulose introduces increased water uptake due to its hydrophilic nature, which could affect the material’s long-term performance in aqueous environments. Despite the higher water absorption, the enhanced mechanical properties of the crosslinked material suggest its potential for use in dental resins, biomedical coatings, and other advanced polymer applications. Future work could focus on improving water stability through further modifications or surface treatments, thereby optimizing the material for real-world applications. Declarations Acknowledgments The laboratory support by the Islamic Azad University, Najafabad Branch is highly acknowledged. Data availability Data will be made available on request. Declarations of Competing Interests The authors declare no competing interests. Declarations of Conflict of Interest The authors declared no potential conflicts of interest concerning this article’s research, authorship, and/ or publication. Ethics approval Not Applicable. Consent for publication Not Applicable. Author Contributions Statement Mehdi Khalaj: Supervisor Maryam Bakhtiy: Methodology, formal analysis Seyed Jalal Hoseyni: Investigation, writing the paper Seyed Mahmoud Musavi: Perform experiments Majid Ghashang: Methodology Funding No funding was received to conduct this study. References Cho, K., Rajan, G., Farrar, P., Prentice, L., & Prusty, B. G. (2022). Dental resin composites: A review on materials to product realizations. Composites Part B: Engineering, 230, 109495. https://doi.org/10.1016/j.compositesb.2021.109495 Leisch, A. F., Sheffield, P. E., Chinn, C., Edelstein, B. L., & Landrigan, P. J. (2010). Bisphenol A and related compounds in dental materials. Pediatrics, 126(4), 760–768. https://doi.org/10.1542/peds.2009-2693 Andrew, J. J., & Dhakal, H. N. (2022). Sustainable biobased composites for advanced applications: Recent trends and future opportunities – A critical review. 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Cellulose, 28, 1893–1931. https://doi.org/10.1007/s10570-020-03674-w Torkian, P., Mortazavi Najafabadi, S., Grzelczyk, D., & Ghashang, M. (2024). TiO 2 bonded SiO 2 -alkyl-NH 2 grafted cellulose for improving thermal stability, mechanical strength characteristics, and water adsorption capacity. Cellulose 31, 1801-1812. https://doi.org/10.1007/s10570-023-05718-3 Additional Declarations No competing interests reported. Scheme 1 is available in the Supplementary Files section. Supplementary Files Scheme1.png Scheme 1: Preparation of Poly (bis-GMA), Poly (chlorinated bis-GMA), and crosslinked poly(bis-GMA) with cellulose Cite Share Download PDF Status: Posted Version 1 posted You are reading this latest preprint version Research Square lets you share your work early, gain feedback from the community, and start making changes to your manuscript prior to peer review in a journal. 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Also discoverable on Platform About Our Team In Review Editorial Policies Advisory Board Help Center Resources Author Services Accessibility API Access RSS feed Manage Cookie Preferences © Research Square 2026 | ISSN 2693-5015 (online) Privacy Policy Terms of Service Do Not Sell My Personal Information {"props":{"pageProps":{"initialData":{"identity":"rs-6378059","acceptedTermsAndConditions":true,"allowDirectSubmit":true,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":448703008,"identity":"aa1b5141-6739-476f-9c57-67f9f31d7fbd","order_by":0,"name":"Mehdi 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University","correspondingAuthor":false,"prefix":"","firstName":"Majid","middleName":"","lastName":"Ghashang","suffix":""}],"badges":[],"createdAt":"2025-04-04 17:38:16","currentVersionCode":1,"declarations":"","doi":"10.21203/rs.3.rs-6378059/v1","doiUrl":"https://doi.org/10.21203/rs.3.rs-6378059/v1","draftVersion":[],"editorialEvents":[],"editorialNote":"","failedWorkflow":false,"files":[{"id":84816302,"identity":"f5d84987-4fcf-418c-a569-ec9b0ece677d","added_by":"auto","created_at":"2025-06-17 15:39:12","extension":"png","order_by":1,"title":"Figure 1","display":"","copyAsset":false,"role":"figure","size":79340,"visible":true,"origin":"","legend":"\u003cp\u003eFT-IR analysis of chlorinated bis-GMA and crosslinked poly(bis-GMA) with cellulose\u003c/p\u003e","description":"","filename":"1.png","url":"https://assets-eu.researchsquare.com/files/rs-6378059/v1/f1a3ca036133b5849a91d74a.png"},{"id":84816305,"identity":"5f3fc53d-54a4-418a-92bc-fa8d78fe2249","added_by":"auto","created_at":"2025-06-17 15:39:12","extension":"png","order_by":2,"title":"Figure 2","display":"","copyAsset":false,"role":"figure","size":43845,"visible":true,"origin":"","legend":"\u003cp\u003eTGA-DTA analysis of bis-GMA (Right) and crosslinked poly(bis-GMA) with cellulose (Left)\u003c/p\u003e","description":"","filename":"2.png","url":"https://assets-eu.researchsquare.com/files/rs-6378059/v1/f8660a0863eebc2a387195a7.png"},{"id":84816304,"identity":"315039ba-639b-4401-a180-7e5cd2b37892","added_by":"auto","created_at":"2025-06-17 15:39:12","extension":"png","order_by":3,"title":"Figure 3","display":"","copyAsset":false,"role":"figure","size":50958,"visible":true,"origin":"","legend":"\u003cp\u003eWater adsorption of Poly (bis-GMA), Poly (chlorinated bis-GMA), and crosslinked poly(bis-GMA) with cellulose\u003c/p\u003e","description":"","filename":"3.png","url":"https://assets-eu.researchsquare.com/files/rs-6378059/v1/a0b2f54860df0558d6bc288e.png"},{"id":84816306,"identity":"2e6640ef-ae01-4c3a-9d98-16ec9e4df1d5","added_by":"auto","created_at":"2025-06-17 15:39:12","extension":"png","order_by":4,"title":"Figure 4","display":"","copyAsset":false,"role":"figure","size":93232,"visible":true,"origin":"","legend":"\u003cp\u003eCO\u003csub\u003e2\u003c/sub\u003e adsorption-desorption capacity\u003c/p\u003e","description":"","filename":"4.png","url":"https://assets-eu.researchsquare.com/files/rs-6378059/v1/206485e0bdac553f511d77f2.png"},{"id":86550289,"identity":"69a83ebc-76a3-43bc-a2bd-1714fc0051ab","added_by":"auto","created_at":"2025-07-12 03:31:28","extension":"pdf","order_by":0,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":770345,"visible":true,"origin":"","legend":"","description":"","filename":"manuscript.pdf","url":"https://assets-eu.researchsquare.com/files/rs-6378059/v1/d0b6e3e7-36b9-4e38-a5ba-fed7d516ceff.pdf"},{"id":85057789,"identity":"a3a78075-f9e9-4d9a-9717-48a716b15f63","added_by":"auto","created_at":"2025-06-20 13:15:41","extension":"png","order_by":1,"title":"","display":"","copyAsset":false,"role":"supplement","size":77099,"visible":true,"origin":"","legend":"\u003cp\u003e\u003cstrong\u003eScheme 1: \u003c/strong\u003ePreparation of Poly (bis-GMA), Poly (chlorinated bis-GMA), and crosslinked poly(bis-GMA) with cellulose\u003c/p\u003e","description":"","filename":"Scheme1.png","url":"https://assets-eu.researchsquare.com/files/rs-6378059/v1/a6e18886264851a2347cc392.png"}],"financialInterests":"\u003cp\u003eNo competing interests reported.\u003c/p\u003e\n\u003cp\u003e\u003cbr\u003e\u003c/p\u003e\n\u003cp\u003eScheme 1 is available in the Supplementary Files section.\u003c/p\u003e","formattedTitle":"Increasing the environmental impact and biocompatibility of poly(bis-GMA) dental resin using crosslinking with amended cellulose","fulltext":[{"header":"Introduction","content":"\u003cp\u003eDental restorative materials based on bisphenol A glycidyl methacrylate (Bis-GMA) have been widely utilized due to their superior mechanical properties, aesthetic advantages, and ease of application. However, their environmental impact and biocompatibility have been subjects of growing concern (Cho et al. \u003cspan citationid=\"CR5\" class=\"CitationRef\"\u003e2022\u003c/span\u003e). Bis-GMA-based resins have been reported to release residual monomers, including bisphenol A (BPA), which has potential estrogenic effects and cytotoxicity, raising concerns about their long-term safety for both patients and dental practitioners. Additionally, conventional polymerization techniques often result in the incomplete conversion of monomers to polymer, leading to compromised mechanical stability and the potential for degradation over time (Cho et al. \u003cspan citationid=\"CR5\" class=\"CitationRef\"\u003e2022\u003c/span\u003e, Leisch et al. \u003cspan citationid=\"CR10\" class=\"CitationRef\"\u003e2010\u003c/span\u003e). To overcome the limitations of traditional dental composites, recent research has emphasized the integration of bio-based materials to enhance biocompatibility, mechanical resilience, and sustainability (Andrew et al. 2022). Conventional methacrylate-based monomers, commonly used in dental formulations, undergo radical polymerization to create durable crosslinked structures. However, this process often yields inconsistent polymer networks, leading to undesirable properties such as polymerization shrinkage, water sorption, and high internal stress (Aminoroaya et al. \u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e2021\u003c/span\u003e). Furthermore, highly viscous monomers, such as Bis-GMA, hinder efficient filler incorporation and reduce overall workability. To address these challenges, researchers have developed bio-derived methacrylate monomers with improved characteristics. High-molecular-weight bio-based monomers have been synthesized to reduce shrinkage strain and enhance structural stability. Some of these features include bulky aliphatic or aromatic ring systems, which contribute to reduced stress development while maintaining optimal mechanical performance (Aminoroaya et al. \u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e2021\u003c/span\u003e, Pfeifer et al. \u003cspan citationid=\"CR15\" class=\"CitationRef\"\u003e2011\u003c/span\u003e, Inagaki et al. \u003cspan citationid=\"CR9\" class=\"CitationRef\"\u003e2016\u003c/span\u003e, Łukaszczyk et al. \u003cspan citationid=\"CR12\" class=\"CitationRef\"\u003e2013\u003c/span\u003e). Additionally, alternatives to triethylene glycol dimethacrylate (TEGDMA), a commonly used diluent known for its cytotoxic potential and polymerization shrinkage, have been explored. Bio-based low-viscosity monomers such as acetyloxypropylene dimethacrylate (Acet-GDMA), ethoxylated isosorbide dimethacrylate (ISETMDA), and poly(propylene glycol) dimethacrylate (PPGDMA) offer reduced shrinkage and improved biocompatibility while preserving mechanical integrity. Another critical research direction focuses on replacing Bis-GMA to minimize exposure to bisphenol-A derivatives. Bio-derived monomers based on isosorbide have demonstrated lower toxicity while maintaining a balance between rigidity and flexibility, ensuring comparable or superior mechanical properties. Structural modifications of Bis-GMA itself have also yielded promising results, with novel derivatives exhibiting reduced water uptake, enhanced hydrophobicity, and minimized shrinkage. By integrating these bio-based alternatives, dental composites can achieve better performance, increased longevity, and reduced environmental impact, marking a significant step toward safer and more sustainable restorative materials (He et al. \u003cspan citationid=\"CR7\" class=\"CitationRef\"\u003e2012\u003c/span\u003e, Gon\u0026ccedil;alves et al. \u003cspan citationid=\"CR6\" class=\"CitationRef\"\u003e2008\u003c/span\u003e, Nie et al. \u003cspan citationid=\"CR14\" class=\"CitationRef\"\u003e2001\u003c/span\u003e, Huang et al. \u003cspan citationid=\"CR8\" class=\"CitationRef\"\u003e2018\u003c/span\u003e, Schoerpf et al. \u003cspan citationid=\"CR17\" class=\"CitationRef\"\u003e2019\u003c/span\u003e, Ligon-Auer et al. \u003cspan citationid=\"CR11\" class=\"CitationRef\"\u003e2016\u003c/span\u003e, Nguyen et al. \u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e2018\u003c/span\u003e, Podg\u0026oacute;rski \u003cspan citationid=\"CR16\" class=\"CitationRef\"\u003e2010\u003c/span\u003e, Walters et al. \u003cspan citationid=\"CR20\" class=\"CitationRef\"\u003e2016\u003c/span\u003e, Berlanga Duarte et al. \u003cspan citationid=\"CR3\" class=\"CitationRef\"\u003e2017\u003c/span\u003e).\u003c/p\u003e \u003cp\u003eAmong the promising strategies is the integration of modified cellulose as a crosslinking agent in poly(Bis-GMA) resins. Cellulose, a naturally abundant and renewable biopolymer, possesses high mechanical strength, excellent biocompatibility, and the ability to form hydrogen bonds, which can significantly improve polymer network formation. Recent advancements in cellulose modification techniques, such as surface functionalization and nanoparticle incorporation, have demonstrated their potential to enhance the mechanical, thermal, and biological performance of dental materials (Carolin et al. \u003cspan citationid=\"CR4\" class=\"CitationRef\"\u003e2023\u003c/span\u003e, Seddiqi et al. \u003cspan citationid=\"CR18\" class=\"CitationRef\"\u003e2021\u003c/span\u003e).\u003c/p\u003e \u003cp\u003eBy leveraging cellulose\u0026rsquo;s unique properties, crosslinking Bis-GMA with modified cellulose can lead to improved polymerization efficiency, reduced monomer release, and enhanced biodegradability, thereby addressing both the biocompatibility and environmental concerns associated with traditional dental resins. This approach aligns with the global movement toward sustainable dentistry, which seeks to minimize the ecological footprint of dental materials while ensuring patient safety and optimal clinical performance. Further exploration of cellulose-based crosslinking mechanisms, along with their impact on the physicochemical properties of Bis-GMA composites, is critical for the next generation of high-performance dental resins.\u003c/p\u003e \u003cp\u003eThis work aimed to synthesize and characterize crosslinked poly(Bis-GMA) with cellulose using a chemical modification approach. The study focused on enhancing the properties of poly(Bis-GMA) by incorporating cellulose into the polymer network to improve its mechanical performance, hydrophilicity, and biodegradability. The modification process involved three key steps: polymerization of Bis-GMA, chlorination of poly(Bis-GMA), and crosslinking with cellulose. Through various analytical techniques, including CHN analysis, FT-IR, TGA-DTA, and mechanical testing, the study explored the resulting crosslinked material's structural, thermal, and mechanical properties.\u003c/p\u003e"},{"header":"Experimental","content":"\u003cp\u003e\u003cstrong\u003e2.1. Reagents and Instrumentation:\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eAll solvents, reagents, and specific chemicals from Merck and Sigma-Aldrich companies were purchased from commercial suppliers. he Shimadzu TGA-DTG-60H instrument was used to measure the thermal behavior of the samples\u003csub\u003e.\u0026nbsp;\u003c/sub\u003eThe Bruker IR spectrophotometer was used for the\u0026nbsp;FT-IR analysis on a KBr disk between 400 to 4000 cm\u003csup\u003e-1\u003c/sup\u003e.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e2.2.Synthesis of Poly(bis-GMA)\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eIn a 500 mL balloon equipped with a condenser, 50g of 4,4′-Isopropylidenediphenol dimethacrylate (bis-GMA, Sigma-Aldrich, 98%) was dissolved in toluene and mixed with 0.3 wt.% of 2,2′-azobis(2-methylpropionitrile) (AIBN; Sigma-Aldrich, ≥98.0%). The mixture was stirred at 80°C under a nitrogen atmosphere overnight. The resulting polymer was then dried, ground into a fine powder, and sieved to obtain homogeneous particles.\u003c/p\u003e\n\u003cp\u003eSpecimens with diameters of 3 mm and 6 mm were prepared. The samples were then subjected to thermal curing at 120°C for 2 hours. Afterward, the edges of the samples were smoothed using sandpaper.\u003c/p\u003e\n\u003cp\u003eMechanical tests were conducted using a universal testing machine (Instron 6025) at a speed of 10 mm/min with a force of 100 kN. The diametral tensile strength (DTS) test followed ADA Standard No. 27, while flexural strength (FS), flexural modulus (FM), and compressive strength (CS) measurements adhered to ISO 10477:92 standards.\u003c/p\u003e\n\u003cp\u003eStatistical analysis was performed using ANOVA in Minitab software (p \u0026lt; 0.05). Tukey’s test was used for homogenous data, while the Dunnett post hoc test was applied to analyze non-homogeneous data. Each experiment was repeated three times to ensure accuracy and reliability.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e2.3. Water Absorption Analysis\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThe water absorption properties of the samples were evaluated using specimens measuring 10×10×4 mm\u003csup\u003e3\u003c/sup\u003e under ambient conditions. Before testing, all samples were thoroughly dried, and their initial weights were recorded. Each experiment was conducted in triplicate to ensure reliability. A precision digital balance (Denver, model: AA-200, USA) was used for weighing. The samples were then immersed in sealed containers holding 30 mL of distilled water with a neutral pH (pH = 7) at a constant temperature of 25°C. To monitor the absorption process, the samples were periodically taken out, their surfaces were carefully dried, and they were weighed before being placed back into the water. This procedure was repeated until no further weight change was observed, indicating equilibrium moisture content. Each test was performed three times for consistency.\u003c/p\u003e\n\u003cp\u003eThe percentage of water absorption was determined using the following formula:\u003c/p\u003e\n\u003cp\u003eWater Absorption (%)=(W\u003csub\u003et\u003c/sub\u003e−W\u003csub\u003ei\u003c/sub\u003e)/W\u003csub\u003ei\u003c/sub\u003e×100\u003c/p\u003e\n\u003cp\u003ewhere \u003cem\u003eW\u003csub\u003ei\u003c/sub\u003e\u003c/em\u003e represents the initial weight of the sample, and \u003cem\u003eW\u003csub\u003et\u003c/sub\u003e\u003c/em\u003e denotes its weight at a given time \u003cem\u003et\u003c/em\u003e [20].\u003c/p\u003e"},{"header":"Results and discussion","content":"\u003cdiv id=\"Sec7\" class=\"Section2\"\u003e \u003cp\u003e3.1 Characterization of Crosslinked poly(Bis-GMA) with cellulose\u003c/p\u003e \n\u003cp\u003eThis study employed a chemical modification approach to synthesize crosslinked poly(bis-GMA) with cellulose, as illustrated in Scheme 1. The preparation process involved three key steps: first, the polymerization of bis-GMA to form the base polymer; second, the chlorination of poly(bis-GMA) to introduce reactive sites; and finally, the crosslinking reaction with cellulose to enhance structural integrity and functionality. The introduction of cellulose into the polymer network likely improves mechanical properties, hydrophilicity, and biodegradability, making the modified material potentially suitable for various applications, such as biomedical coatings, dental composites, and sustainable polymeric materials. Further characterization of the crosslinked structure would provide deeper insights into the extent of modification and its impact on the material\u0026rsquo;s thermal and mechanical performance.\u003c/p\u003e\n\u003cp\u003eThe elemental composition of the prepared polymers was assessed through CHN analysis, as presented in Table 1. Poly(bis-GMA) exhibited a carbon content of 67.94%, hydrogen content of 7.08%, and negligible nitrogen content (0.01%). The introduction of chlorine in poly(chlorinated bis-GMA) led to a reduction in carbon (63.15%) and hydrogen (6.58%), which is consistent with the replacement of hydrogen atoms by chlorine, contributing to an increase in overall molecular weight. In contrast, crosslinking poly(bis-GMA) with cellulose resulted in a slight reduction in carbon content (64.87%) and an increase in hydrogen (7.62%) and nitrogen (0.06%). The presence of nitrogen suggests the incorporation of cellulose-derived moieties, potentially due to residual amines from the initial source. The increased hydrogen content aligns with the hydroxyl-rich structure of cellulose, which introduces additional hydrogen-bearing functional groups into the polymer network.\u003c/p\u003e\n\u003ctable border=\"1\" cellspacing=\"0\" cellpadding=\"0\" width=\"516\"\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"4\" valign=\"top\" style=\"width: 516px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eTable 1:\u003c/strong\u003e CHN analysis of prepared samples\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 317px;\"\u003e\n \u003cp\u003ePolymer\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 72px;\"\u003e\n \u003cp\u003e%C\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 60px;\"\u003e\n \u003cp\u003e%H\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 67px;\"\u003e\n \u003cp\u003e%N\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 317px;\"\u003e\n \u003cp\u003ePoly (bis-GMA)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 72px;\"\u003e\n \u003cp\u003e67.94\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 60px;\"\u003e\n \u003cp\u003e7.08\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 67px;\"\u003e\n \u003cp\u003e0.01\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 317px;\"\u003e\n \u003cp\u003ePoly (chlorinated bis-GMA)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 72px;\"\u003e\n \u003cp\u003e63.15\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 60px;\"\u003e\n \u003cp\u003e6.58\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 67px;\"\u003e\n \u003cp\u003e0.01\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 317px;\"\u003e\n \u003cp\u003eCrosslinked poly(bis-GMA) with cellulose\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 72px;\"\u003e\n \u003cp\u003e64.87\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 60px;\"\u003e\n \u003cp\u003e7.62\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 67px;\"\u003e\n \u003cp\u003e0.06\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n\u003c/table\u003e\n\u003cp\u003eFT-IR spectra (Figure 1) provide further confirmation of chemical modifications. In poly(chlorinated bis-GMA), a characteristic C-Cl stretching band appears at approximately 700\u0026ndash;800 cm\u003csup\u003e-1\u003c/sup\u003e, confirming the presence of chlorine atoms. The FT-IR spectrum of crosslinked poly(bis-GMA) with cellulose reveals significant structural modifications, confirming successful crosslinking and interaction between the two components. The appearance of a broad absorption peak at 3701 cm\u003csup\u003e-1\u003c/sup\u003e, associated with N-H stretching, suggests the formation of new amine groups, while peaks at 3032 cm\u003csup\u003e-1\u003c/sup\u003e (=C-H, sp\u003csup\u003e2\u003c/sup\u003e) and 2884 cm\u003csup\u003e-1\u003c/sup\u003e (C-H, sp\u003csup\u003e3\u003c/sup\u003e) indicate the retention of both aromatic and aliphatic C-H bonds. The presence of C=C stretching vibrations at 1625 and 1575 cm\u003csup\u003e-1\u003c/sup\u003e implies benzene rings within the polymer matrix. Additionally, peaks at 1091, 1151, and 1217 cm\u003csup\u003e-1\u0026nbsp;\u003c/sup\u003ecorrespond to C-O, C-N, and C-C bonds. The peak at 1729 cm\u003csup\u003e-1\u003c/sup\u003e is due to the presence of ester groups. These spectral changes confirm a successful modification, with strong intermolecular bonding that could influence the material\u0026apos;s mechanical and thermal properties.\u003c/p\u003e\n\u003cp\u003eThe thermal behavior and stability of bis-GMA and crosslinked poly(bis-GMA) with cellulose were assessed using TGA-DTA analysis, revealing a one-step decomposition process primarily associated with the degradation of the organic polymer chain. An initial weight loss of approximately 2% is observed, corresponding to the removal of adsorbed water and impurities, likely due to the hydrophobic nature of hydroxyl groups in the polymer structure. The main decomposition phase occurs between 350\u0026deg;C and 420\u0026deg;C (Figure 2), indicating the breakdown of the organic backbone, with DTA confirming that this process is exothermic. Notably, the decomposition temperature differs between the two materials, with bis-GMA decomposing at approximately 468\u0026deg;C, whereas the crosslinked poly(bis-GMA) with cellulose decomposes at a lower temperature of 398\u0026deg;C. The reduction in thermal stability after crosslinking suggests that the incorporation of cellulose alters the polymer network, potentially introducing weaker bonds or increasing structural heterogeneity. However, the exothermic nature of degradation indicates that energy is released during polymer breakdown, which is characteristic of crosslinked systems. These findings provide insight into the thermal stability of the material, which could be further explored for applications requiring controlled thermal degradation, such as biomedical, coating, or composite applications.\u003c/p\u003e\n\u003cp\u003eThe mechanical performance of poly(bis-GMA), poly(chlorinated bis-GMA), and crosslinked poly(bis-GMA) with cellulose was assessed based on flexural strength (FS), flexural modulus (FM), diametral tensile strength (DTS), and compressive strength (CS), as presented in Table 2. Poly(bis-GMA) exhibited moderate mechanical properties, with FS of 106.3 MPa, FM of 3.97 GPa, DTS of 24.5 MPa, and CS of 153.2 MPa. Chlorination of bis-GMA resulted in a notable decline in all mechanical parameters, with FS decreasing to 94.4 MPa, FM to 3.19 GPa, DTS to 19.8 MPa, and CS to 139.8 MPa. The reduction in mechanical properties may be attributed to the altered polymer network due to chlorine incorporation, potentially introducing structural defects or reducing crosslink density. In contrast, crosslinking bis-GMA with cellulose significantly enhanced all mechanical properties. The FS increased to 123.36 MPa, FM to 4.67 GPa, DTS to 31.5 MPa, and CS to 186.3 MPa, demonstrating improved load-bearing capacity and fracture resistance. The incorporation of cellulose likely contributed to this enhancement by reinforcing the polymer matrix, increasing rigidity, and improving stress distribution. These findings suggest that cellulose crosslinking effectively strengthens poly(bis-GMA) and could be a promising strategy for improving the mechanical performance of dental resins.\u003c/p\u003e\n\u003ctable border=\"1\" cellspacing=\"0\" cellpadding=\"0\" width=\"602\"\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd colspan=\"5\" valign=\"top\" style=\"width: 602px;\"\u003e\n \u003cp\u003e\u003cstrong\u003eTable 2:\u003c/strong\u003e Mechanical properties \u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 306px;\"\u003e\n \u003cp\u003ePolymer\u0026nbsp;\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 60px;\"\u003e\n \u003cp\u003eFS [MPa]\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 60px;\"\u003e\n \u003cp\u003eFM [GPa]\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 90px;\"\u003e\n \u003cp\u003eDTS [MPa]\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 86px;\"\u003e\n \u003cp\u003eCS [MPa]\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 306px;\"\u003e\n \u003cp\u003ePoly (bis-GMA)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 60px;\"\u003e\n \u003cp\u003e106.3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 60px;\"\u003e\n \u003cp\u003e3.97\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 90px;\"\u003e\n \u003cp\u003e24.5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 86px;\"\u003e\n \u003cp\u003e153.2\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 306px;\"\u003e\n \u003cp\u003ePoly (chlorinated bis-GMA)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 60px;\"\u003e\n \u003cp\u003e94.4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 60px;\"\u003e\n \u003cp\u003e3.19\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 90px;\"\u003e\n \u003cp\u003e19.8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 86px;\"\u003e\n \u003cp\u003e139.8\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd valign=\"top\" style=\"width: 306px;\"\u003e\n \u003cp\u003eCrosslinked poly(bis-GMA) with cellulose\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 60px;\"\u003e\n \u003cp\u003e123.36\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 60px;\"\u003e\n \u003cp\u003e4.67\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 90px;\"\u003e\n \u003cp\u003e31.5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd valign=\"top\" style=\"width: 86px;\"\u003e\n \u003cp\u003e186.3\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n\u003c/table\u003e\n\u003cp\u003e\u003cstrong\u003e3.2. Water Adsorption\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eWater adsorption behavior was evaluated over 64 hours, as shown in Figure 3. Poly(bis-GMA) demonstrated a gradual increase in water adsorption, reaching 4.39% at 64 hours. Chlorination of bis-GMA led to a substantial reduction in water uptake, with adsorption values stabilizing at 1.93% at 64 hours. This reduction may be due to the increased hydrophobicity of the polymer following chlorine substitution, limiting water penetration into the polymer matrix. Conversely, crosslinked poly(bis-GMA) with cellulose exhibited the highest water adsorption, reaching 20.18% at 64 hours. The significant increase in water uptake can be attributed to the hydrophilic nature of cellulose, which contains hydroxyl groups capable of forming hydrogen bonds with water molecules. Although cellulose reinforcement enhanced mechanical properties, the increased water adsorption may raise concerns about long-term stability and degradation in aqueous environments. Future modifications, such as surface treatments or hybrid crosslinking strategies, could help mitigate excessive water uptake while maintaining the mechanical advantages provided by cellulose reinforcement.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003e3.3. CO\u003csub\u003e2\u003c/sub\u003e adsorption-desorption studies\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThe CO\u003csub\u003e2\u003c/sub\u003e adsorption capacity of crosslinked poly(bis-GMA) with cellulose was measured using the mass-increasing method, with the results detailed in Figure 4. The functional groups present, such as NH and OH, were key in enhancing the adsorbent\u0026apos;s efficiency in capturing CO\u003csub\u003e2\u003c/sub\u003e gas. The adsorption-desorption process was conducted in three stages. Initially, the sample was degassed at 145\u0026deg;C under N\u003csub\u003e2\u003c/sub\u003e gas flow, then cooled to 45\u0026deg;C and purged with N\u003csub\u003e2\u003c/sub\u003e for 30 minutes. The CO\u003csub\u003e2\u003c/sub\u003e adsorption phase followed, using a CO\u003csub\u003e2\u003c/sub\u003e/N\u003csub\u003e2\u003c/sub\u003e mixture (30% CO\u003csub\u003e2\u003c/sub\u003e) at a flow rate of 60 mL/min. In the final stage, CO\u003csub\u003e2\u003c/sub\u003e desorption was facilitated by passing N\u003csub\u003e2\u003c/sub\u003e over the sample at a reduced temperature of 10\u0026deg;C/min, aiding the release of CO\u003csub\u003e2\u003c/sub\u003e from the material\u0026apos;s surface. The data showed that crosslinked poly(bis-GMA) with cellulose could adsorb up to 403 mg of CO\u003csub\u003e2\u003c/sub\u003e per gram of adsorbent, indicating substantial adsorption potential\u003c/p\u003e"},{"header":"Conclusion","content":"\u003cp\u003eIn this study, crosslinked poly(bis-GMA) with cellulose was successfully synthesized through a three-step chemical modification process involving polymerization, chlorination, and crosslinking. The incorporation of cellulose into the poly(bis-GMA) network significantly enhanced the material\u0026apos;s mechanical properties, as evidenced by increased flexural strength, flexural modulus, diametral tensile strength, and compressive strength. FT-IR analysis confirmed the formation of new functional groups, while TGA-DTA analysis revealed that crosslinking with cellulose reduces thermal stability, suggesting structural changes in the polymer matrix. Water adsorption studies indicated that cellulose introduces increased water uptake due to its hydrophilic nature, which could affect the material\u0026rsquo;s long-term performance in aqueous environments. Despite the higher water absorption, the enhanced mechanical properties of the crosslinked material suggest its potential for use in dental resins, biomedical coatings, and other advanced polymer applications. Future work could focus on improving water stability through further modifications or surface treatments, thereby optimizing the material for real-world applications.\u003c/p\u003e"},{"header":"Declarations","content":"\u003cp\u003e\u003cstrong\u003eAcknowledgments\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThe laboratory support by the\u0026nbsp;Islamic Azad University, Najafabad Branch is highly acknowledged.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eData availability\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eData will be made available on request.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eDeclarations of Competing Interests\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThe authors declare no competing interests.\u0026nbsp;\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eDeclarations of Conflict of Interest\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThe authors declared no potential conflicts of interest concerning this article’s research, authorship, and/ or publication.\u0026nbsp;\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eEthics approval\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eNot Applicable.\u0026nbsp;\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eConsent for publication\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eNot Applicable.\u0026nbsp;\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eAuthor Contributions Statement\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eMehdi Khalaj: Supervisor\u003c/p\u003e\n\u003cp\u003eMaryam Bakhtiy: Methodology, formal analysis\u003c/p\u003e\n\u003cp\u003eSeyed Jalal Hoseyni: Investigation, writing the paper\u003c/p\u003e\n\u003cp\u003eSeyed Mahmoud Musavi: Perform experiments\u003c/p\u003e\n\u003cp\u003eMajid Ghashang: Methodology\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eFunding\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eNo funding was received to conduct this study.\u003c/p\u003e"},{"header":"References","content":"\u003col\u003e\n\u003cli\u003eCho, K., Rajan, G., Farrar, P., Prentice, L., \u0026amp; Prusty, B. 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TiO\u003csub\u003e2\u003c/sub\u003e bonded SiO\u003csub\u003e2\u003c/sub\u003e-alkyl-NH\u003csub\u003e2\u003c/sub\u003e grafted cellulose for improving thermal stability, mechanical strength characteristics, and water adsorption capacity. Cellulose 31, 1801-1812. https://doi.org/10.1007/s10570-023-05718-3\u003c/li\u003e\n\u003c/ol\u003e"}],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":true,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":false,"hideJournal":true,"highlight":"","institution":"","isAcceptedByJournal":false,"isAuthorSuppliedPdf":false,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":false,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"researchsquare","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":true,"externalIdentity":"","sideBox":"","snPcode":"","submissionUrl":"/submission","title":"Research Square","twitterHandle":"researchsquare","acdcEnabled":true,"dfaEnabled":false,"editorialSystem":"","reportingPortfolio":"","inReviewEnabled":false,"inReviewRevisionsEnabled":true},"keywords":"Biocompatibility, poly(Bis-GMA), dental resin, cellulose, crosslinked polymers","lastPublishedDoi":"10.21203/rs.3.rs-6378059/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-6378059/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eThis study investigates the synthesis and characterization of crosslinked poly(Bis-GMA) with cellulose using a chemical modification approach. The preparation involves three key steps: polymerization of bisphenol A glycidyl methacrylate (Bis-GMA), chlorination of poly(Bis-GMA), and crosslinking with cellulose. The resulting materials were characterized using CHN analysis, FT-IR, TGA-DTA, and mechanical testing. CHN analysis revealed changes in elemental composition due to chlorination and cellulose incorporation. At the same time, FT-IR confirmed successful chemical modifications, with the formation of new functional groups such as N-H and C-O bonds. TGA-DTA analysis indicated a decrease in thermal stability after crosslinking, with crosslinked poly(Bis-GMA) with cellulose decomposing at a lower temperature than Bis-GMA. Mechanical testing showed enhanced properties in the crosslinked material, with improved flexural strength, flexural modulus, diametral tensile strength, and compressive strength, likely due to the reinforcing effect of cellulose. Water adsorption studies highlighted the hydrophilic nature of cellulose, leading to increased water uptake in the crosslinked material. These findings suggest that cellulose-crosslinked poly(bis-GMA) offers improved mechanical properties and could be a promising material for applications in dental composites, biomedical coatings, and other polymer-based systems, though further modifications may be necessary to address water stability issues.\u003c/p\u003e","manuscriptTitle":"Increasing the environmental impact and biocompatibility of poly(bis-GMA) dental resin using crosslinking with amended cellulose","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2025-06-17 15:39:08","doi":"10.21203/rs.3.rs-6378059/v1","editorialEvents":[{"type":"communityComments","content":0}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"researchsquare","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":true,"externalIdentity":"","sideBox":"","snPcode":"","submissionUrl":"/submission","title":"Research Square","twitterHandle":"researchsquare","acdcEnabled":true,"dfaEnabled":false,"editorialSystem":"","reportingPortfolio":"","inReviewEnabled":false,"inReviewRevisionsEnabled":true}}],"origin":"","ownerIdentity":"9e769e65-ce2a-45ec-86bf-03371cf1bb14","owner":[],"postedDate":"June 17th, 2025","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"posted","subjectAreas":[],"tags":[],"updatedAt":"2025-07-12T03:23:17+00:00","versionOfRecord":[],"versionCreatedAt":"2025-06-17 15:39:08","video":"","vorDoi":"","vorDoiUrl":"","workflowStages":[]},"version":"v1","identity":"rs-6378059","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-6378059","identity":"rs-6378059","version":["v1"]},"buildId":"8U1c8b4HqxoKbykW_rLl7","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}