{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,29]],"date-time":"2026-10-29T18:20:26Z","timestamp":1793298026882,"version":"4.5.0"},"reference-count":35,"publisher":"American Chemical Society (ACS)","issue":"28","license":[{"start":{"date-parts":[[2024,7,4]],"date-time":"2024-07-04T00:00:00Z","timestamp":1720051200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100004704","name":"National Research Council of Thailand","doi-asserted-by":"publisher","award":["N41A640180"],"award-info":[{"award-number":["N41A640180"]}],"id":[{"id":"10.13039\/501100004704","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100007056","name":"National Nanotechnology Center","doi-asserted-by":"publisher","award":["P2150472"],"award-info":[{"award-number":["P2150472"]}],"id":[{"id":"10.13039\/501100007056","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100007056","name":"National Nanotechnology Center","doi-asserted-by":"publisher","award":["P2151043"],"award-info":[{"award-number":["P2151043"]}],"id":[{"id":"10.13039\/501100007056","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100007540","name":"National Metal and Materials Technology Center","doi-asserted-by":"publisher","award":["P2050350"],"award-info":[{"award-number":["P2050350"]}],"id":[{"id":"10.13039\/501100007540","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2024,7,16]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Herein, a furan-based methacrylate oligomer (FBMO) featuring imine functional groups was synthesized for application in stereolithography. The preparation involved the imination reaction of 5-hydroxymethylfurfural (5-HMF) and amino ethanol. Utilizing 5-HMF as a sustainable building block for furan-based polymers, FBMO was formulated and subsequently integrated into photosensitive resin formulations along with methacrylate-containing diluents, such as PEGDMA and TEGDMA. The synthesized furan-based methacrylate oligomers underwent comprehensive characterization using FTIR, 1H NMR spectroscopy, and size exclusion chromatography. The impact of methacrylate-containing diluents on various properties of the formulated resins and the resulting 3D-printed specimens was systematically evaluated. This assessment included an analysis of rheological behavior, printing fidelity, mechanical properties, thermal stability, surface morphology, and cytotoxicity. By adjusting the ratios of FBMO to methacrylate-containing diluents within the range of 50:50 to 90:10, the viscosity of the resulting resins was controlled to fall within 0.04 to 0.28 Pa s at a shear rate of 10 s\u20131. The 3D-printed specimens exhibited precise conformity to the computer-aided design (CAD) model and demonstrated compressive moduli ranging from 0.53 \u00b1 0.04 to 144 \u00b1 6.70 MPa, dependent on the resin formulation and internal structure. Furthermore, cytotoxicity assessments revealed that the 3D-printed specimens were noncytotoxic to porcine chondrocytes. In conclusion, we introduce a new strategy to prepare the furan-based methacrylate oligomer (FBMO) and 3D-printed specimens with adjustable properties using stereolithography, which can be further utilized for appropriate applications.<\/jats:p>","DOI":"10.1021\/acsomega.4c03274","type":"journal-article","created":{"date-parts":[[2024,7,4]],"date-time":"2024-07-04T23:03:43Z","timestamp":1720134223000},"page":"30771-30781","source":"Crossref","is-referenced-by-count":6,"title":["Synthesis and Characterization of Furan-Based Methacrylate\nOligomers Containing the Imine Functional Group for Stereolithography"],"prefix":"10.1021","volume":"9","author":[{"given":"Nuttapol","family":"Risangud","sequence":"first","affiliation":[{"name":"National Science and Technology Development Agency , , 111 Thailand Science Park, Phahonyothin Road , , ,","place":["Klong Luang, Pathum Thani, Thailand, 12120"]},{"name":"Chulalongkorn University , , ,","place":["Bangkok, Thailand, 10330"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jittima","family":"Mama","sequence":"additional","affiliation":[{"name":"National Science and Technology Development Agency , , 111 Thailand Science Park, Paholyothin Road, Klong 1 , , ,","place":["Klong Luang, Pathumthani, Thailand, 12120"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Piyarat","family":"Sungkhaphan","sequence":"additional","affiliation":[{"name":"National Science and Technology Development Agency , , 111 Thailand Science Park, Phahonyothin Road , , ,","place":["Klong Luang, Pathum Thani, Thailand, 12120"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Puttipong","family":"Pananusorn","sequence":"additional","affiliation":[{"name":"Vidyasirimedhi Institute of Science and Technology (VISTEC) , , Wangchan , ,","place":["Rayong, Thailand, 21210"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Orawan","family":"Termkunanon","sequence":"additional","affiliation":[{"name":"National Science and Technology Development Agency , , 111 Thailand Science Park, Paholyothin Road, Klong 1 , , ,","place":["Klong Luang, Pathumthani, Thailand, 12120"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Muhammad Sulthan","family":"Arkana","sequence":"additional","affiliation":[{"name":"Chulalongkorn University , , ,","place":["Bangkok, Thailand, 10330"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Supang","family":"Sripraphot","sequence":"additional","affiliation":[{"name":"National Science and Technology Development Agency , , 111 Thailand Science Park, Paholyothin Road, Klong 1 , , ,","place":["Klong Luang, Pathumthani, Thailand, 12120"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5606-5493","authenticated-orcid":true,"given":"Tareerat","family":"Lertwimol","sequence":"additional","affiliation":[{"name":"National Science and Technology Development Agency , , 111 Thailand Science Park, Phahonyothin Road , , ,","place":["Klong Luang, Pathum Thani, Thailand, 12120"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9938-6788","authenticated-orcid":true,"given":"Somprasong","family":"Thongkham","sequence":"additional","affiliation":[{"name":"National Science and Technology Development Agency , , 111 Thailand Science Park, Paholyothin Road, Klong 1 , , ,","place":["Klong Luang, Pathumthani, Thailand, 12120"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2024,7,4]]},"reference":[{"key":"2026081708345928900_cit1","doi-asserted-by":"publisher","first-page":"625","DOI":"10.3390\/polym14030625","article-title":"Recent Progress\non Bio-Based Polyesters Derived from 2,5-Furandicarbonxylic\nAcid (FDCA)","volume":"14","author":"Fei","year":"2022","journal-title":"Polymers"},{"issue":"3","key":"2026081708345928900_cit2","doi-asserted-by":"publisher","first-page":"796","DOI":"10.1021\/ma3023298","article-title":"Poly\u00ad(Butylene 2,5-Furan Dicarboxylate), a biobased\nAlternative to PBT: Synthesis, Physical Properties, and Crystal Structure","volume":"46","author":"Zhu","year":"2013","journal-title":"Macromolecules"},{"key":"2026081708345928900_cit3","doi-asserted-by":"publisher","first-page":"28","DOI":"10.1016\/j.polymer.2015.01.080","article-title":"Synthesis of the\nBio-Based Polyester Poly\u00ad(Propylene 2,5-Furan Dicarboxylate). Comparison\nof Thermal Behavior and Solid State Structure with Its Terephthalate\nand Naphthalate Homologues","volume":"62","author":"Papageorgiou","year":"2015","journal-title":"Polymer (Guildf)"},{"key":"2026081708345928900_cit4","doi-asserted-by":"publisher","first-page":"379","DOI":"10.1016\/j.eurpolymj.2018.10.014","article-title":"Highly Crystalline\nPolyesters Synthesized from Furandicarboxylic Acid (FDCA): Potential\nBio-Based Engineering Plastic","volume":"109","author":"Wang","year":"2018","journal-title":"Eur. Polym. J."},{"issue":"2","key":"2026081708345928900_cit5","doi-asserted-by":"publisher","first-page":"455","DOI":"10.1007\/s12010-020-03325-7","article-title":"Bioconversion of 5-Hydroxymethylfurfural\n(HMF) to 2,5-Furandicarboxylic Acid (FDCA) by a Native Obligate Aerobic\nBacterium, Acinetobacter Calcoaceticus NL14","volume":"192","author":"Sheng","year":"2020","journal-title":"Appl. Biochem. Biotechnol."},{"issue":"24","key":"2026081708345928900_cit6","doi-asserted-by":"publisher","first-page":"15940","DOI":"10.1021\/acsomega.1c01607","article-title":"High-Yield\nand High-Efficiency Conversion of HMF to levulinic Acid in a Green\nand Facile Catalytic Process by a Dual-Function Bro\u0337nsted-Lewis\nAcid HScCl4Catalyst","volume":"6","author":"Liu","year":"2021","journal-title":"ACS Omega"},{"key":"2026081708345928900_cit7","doi-asserted-by":"publisher","first-page":"30875","DOI":"10.1039\/C8RA05308A","article-title":"Efficient Conversion\nof 5-Hydroxymethylfurfural to High-Value Chemicals by Chemo- and Bio-Catalysis","volume":"8","author":"Xia","year":"2018","journal-title":"RSC Adv."},{"issue":"6","key":"2026081708345928900_cit8","doi-asserted-by":"publisher","first-page":"3585","DOI":"10.1039\/D0RA10307A","article-title":"Efficient Synthesis of 5-Ethoxymethylfurfural\nfrom Biomass-Derived 5-Hydroxymethylfurfural over Sulfonated Organic\nPolymer Catalyst","volume":"11","author":"Xiang","year":"2021","journal-title":"RSC Adv."},{"issue":"3","key":"2026081708345928900_cit9","doi-asserted-by":"publisher","first-page":"664","DOI":"10.1007\/s10971-019-05047-7","article-title":"The Hydrogenation\nof 5-Hydroxymethylfurfural (HMF) to 2,5-Dimethylfuran (DMF) with Sol\u2013Gel\nRu-Co\/SiO2 Catalyst","volume":"91","author":"Esen","year":"2019","journal-title":"J. Solgel Sci. Technol."},{"key":"2026081708345928900_cit10","doi-asserted-by":"publisher","first-page":"8991","DOI":"10.1021\/acsomega.2c07629","article-title":"biobased 2,5-Bis\u00ad(Hydroxymethyl)\u00adFuran as a Versatile Building Block\nfor Sustainable Polymeric Materials","volume":"8","author":"Post","year":"2023","journal-title":"ACS Omega"},{"issue":"12","key":"2026081708345928900_cit11","doi-asserted-by":"publisher","DOI":"10.1016\/j.Heliyon.2022.e12081","article-title":"Hydroxymethyl\nFurfural (HMF) a High Strength Cellulose Resin for Wood Composite\nLaminates","volume":"8","author":"Moses","year":"2022","journal-title":"Heliyon"},{"issue":"20","key":"2026081708345928900_cit12","doi-asserted-by":"publisher","first-page":"5532","DOI":"10.1039\/C9GC01859J","article-title":"Synthesis of Biomass-Derived\nFeedstocks for the Polymers and Fuels Industries from 5-(Hydroxymethyl)\u00adFurfural\n(HMF) and Acetone","volume":"21","author":"Chang","year":"2019","journal-title":"Green Chem."},{"key":"2026081708345928900_cit13","doi-asserted-by":"publisher","first-page":"16641","DOI":"10.1021\/acsomega.1c02075","article-title":"Sulfuric\nAcid-Catalyzed Dehydratization of Carbohydrates for the Production\nof Adhesive Precursors","volume":"6","author":"Sailer-Kronlachner","year":"2021","journal-title":"ACS Omega"},{"issue":"11","key":"2026081708345928900_cit14","doi-asserted-by":"publisher","first-page":"9659","DOI":"10.1021\/acsapm.3c02207","article-title":"Furanic\n(Meth)\u00adacrylate Monomers as Sustainable Reactive\nDiluents for stereolithography","volume":"5","author":"Hevus","year":"2023","journal-title":"ACS Appl. Polym.\nMater."},{"key":"2026081708345928900_cit15","doi-asserted-by":"publisher","DOI":"10.1016\/j.eurpolymj.2023.111872","article-title":"Bio-Based Additive\nManufacturing Materials: An in-Depth Structure-Property Relationship\nStudy of UV-Curing Polyesters from itaconic Acid","volume":"186","author":"Papadopoulos","year":"2023","journal-title":"Eur. Polym. J."},{"issue":"7","key":"2026081708345928900_cit16","doi-asserted-by":"publisher","first-page":"1069","DOI":"10.1007\/s10118-023-2904-8","article-title":"Modifying\nPoly\u00ad(Propylene Carbonate) with Furan-Based Non-Isocyanate Polyurethanes","volume":"41","author":"Li","year":"2023","journal-title":"Chinese Journal of Polymer Science (English Edition)"},{"issue":"8","key":"2026081708345928900_cit17","doi-asserted-by":"publisher","first-page":"698","DOI":"10.3390\/toxics11080698","article-title":"Synthesis and Biodegradation Test\nof a New polyether Polyurethane Foam Produced from PEG 400, L-Lysine\nEthyl Ester Diisocyanate (L-LDI) and Bis-Hydroxymethyl Furan (BHMF)","volume":"11","author":"Olivito","year":"2023","journal-title":"Toxics"},{"issue":"9","key":"2026081708345928900_cit18","doi-asserted-by":"publisher","first-page":"895","DOI":"10.1007\/s13233-019-7123-3","article-title":"Thermally\nhealable Polyurethanes Based on Furfural-Derived Monomers via Baylis-Hillman\nReaction","volume":"27","author":"Huang","year":"2019","journal-title":"Macromol. Res."},{"key":"2026081708345928900_cit19","doi-asserted-by":"publisher","first-page":"172","DOI":"10.1016\/j.compositesb.2018.02.012","article-title":"Additive Manufacturing\n(3D Printing): A Review of Materials, Methods Applications and Challenges","volume":"143","author":"Ngo","year":"2018","journal-title":"Composites Part B: Engineering"},{"key":"2026081708345928900_cit20","doi-asserted-by":"publisher","DOI":"10.1016\/j.polymer.2023.126657","article-title":"A photocurable\nPolyurethane Elastomer for Digital Light Processing with Comprehensive\nReusability Based on Dynamic Hindered Urea Bonds","volume":"292","author":"Zhang","year":"2024","journal-title":"Polymer (Guildf)"},{"key":"2026081708345928900_cit21","doi-asserted-by":"publisher","DOI":"10.1016\/j.matdes.2019.107905","article-title":"3D Printed\nCork\/Polyurethane Composite\nFoams","volume":"179","author":"Gama","year":"2019","journal-title":"Mater. Des"},{"key":"2026081708345928900_cit22","doi-asserted-by":"publisher","first-page":"68","DOI":"10.1038\/s41529-022-00277-7","article-title":"Recent Advances\nin Biodegradable Polymers for Sustainable Applications","volume":"6","author":"Samir","year":"2022","journal-title":"npj Mater. Degrad."},{"key":"2026081708345928900_cit23","doi-asserted-by":"publisher","first-page":"331","DOI":"10.1007\/s40964-022-00336-0","article-title":"Additive Manufacturing by Digital Light Processing:\nA Review","volume":"8","author":"Chaudhary","year":"2023","journal-title":"Progress in Additive Manufacturing"},{"key":"2026081708345928900_cit24","doi-asserted-by":"publisher","first-page":"593","DOI":"10.1021\/acsapm.8b00165","article-title":"photopolymerization\nin 3D Printing","volume":"1","author":"Bagheri","year":"2019","journal-title":"ACS Applied\nPolymer Materials"},{"key":"2026081708345928900_cit25","doi-asserted-by":"publisher","DOI":"10.1016\/j.cej.2022.139401","article-title":"Recyclable and Reprintable biobased photopolymers for Digital Light\nProcessing 3D Printing","volume":"452","author":"Zhu","year":"2023","journal-title":"Chemical Engineering\nJournal"},{"issue":"24","key":"2026081708345928900_cit26","doi-asserted-by":"publisher","first-page":"7818","DOI":"10.1021\/acssuschemeng.2c01806","article-title":"3D Printable Sustainable Composites with Thermally Tunable Properties\nEntirely from Corn-Based Products","volume":"10","author":"Islam","year":"2022","journal-title":"ACS Sustain\nChem. Eng."},{"key":"2026081708345928900_cit27","doi-asserted-by":"publisher","DOI":"10.3389\/fbioe.2023.1234340","article-title":"Biomaterials-Based\nAdditive Manufacturing for Customized Bioengineering in Management\nof Otolaryngology: A Comprehensive Review","volume":"11","author":"Vyas","year":"2023","journal-title":"Front.\nBioeng. Biotechnol."},{"issue":"22","key":"2026081708345928900_cit28","doi-asserted-by":"publisher","first-page":"27110","DOI":"10.1021\/acsami.3c01669","article-title":"biobased photopolymer Resin for 3D\nPrinting Containing Dynamic Imine Bonds for Fast Reprocessability","volume":"15","author":"Stouten","year":"2023","journal-title":"ACS Appl. Mater. Interfaces"},{"issue":"18","key":"2026081708345928900_cit29","doi-asserted-by":"publisher","first-page":"5455","DOI":"10.3390\/molecules26185455","article-title":"Rubber Seed Oil-Based\nUv-Curable Polyurethane acrylate Resins for Digital Light Processing\n(Dlp) 3d Printing","volume":"26","author":"Hu","year":"2021","journal-title":"Molecules"},{"issue":"9","key":"2026081708345928900_cit30","doi-asserted-by":"publisher","first-page":"1886","DOI":"10.3390\/polym14091886","article-title":"Preparation\nand Characterization of 3D-Printed biobased Composites Containing\nMicro-or Nanocrystalline Cellulose","volume":"14","author":"Rosa","year":"2022","journal-title":"Polymers\n(Basel)"},{"key":"2026081708345928900_cit31","doi-asserted-by":"publisher","first-page":"209","DOI":"10.1016\/j.addma.2018.03.013","article-title":"Hot Lithography\nvs. Room Temperature DLP 3D-Printing of a dimethacrylate","volume":"21","author":"Steyrer","year":"2018","journal-title":"Addit Manuf"},{"issue":"42","key":"2026081708345928900_cit32","doi-asserted-by":"publisher","DOI":"10.1002\/app.51391","article-title":"Poly\u00ad(Ester-Co-Glycidyl\nMethacrylate)\nfor Digital Light Processing in Biomedical Applications","volume":"138","author":"Risangud","year":"2021","journal-title":"J. Appl. Polym. Sci."},{"key":"2026081708345928900_cit33","doi-asserted-by":"publisher","DOI":"10.1016\/j.coco.2023.101506","article-title":"Methacrylated Wood Flour-Reinforced \u201cAll-Wood\u201d\nDerived Resin for Digital Light Processing (DLP) 3D Printing","volume":"38","author":"Yao","year":"2023","journal-title":"Compos. Commun."},{"key":"2026081708345928900_cit34","doi-asserted-by":"publisher","DOI":"10.1016\/j.apmt.2021.101060","article-title":"DLP 3D \u2013\nPrinting of Shape Memory Polymers Stabilized by Thermoreversible Hydrogen\nBonding Interactions","volume":"23","author":"Cosola","year":"2021","journal-title":"Appl. Mater. Today"},{"issue":"21","key":"2026081708345928900_cit35","doi-asserted-by":"publisher","first-page":"4518","DOI":"10.3390\/polym14214518","article-title":"The 3D\nprintability and Mechanical Properties of Polyhydroxybutyrate (PHB)\nas Additives in Urethane dimethacrylate (UDMA) Blends Polymer for\nMedical Application","volume":"14","author":"Abu\nBakar","year":"2022","journal-title":"Polymers (Basel)"}],"container-title":["ACS Omega"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acsomega.4c03274","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/9\/28\/30771\/4829260\/ao4c03274.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/9\/28\/30771\/4829260\/ao4c03274.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T12:46:04Z","timestamp":1786970764000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/acsodf\/article\/9\/28\/30771\/460532\/Synthesis-and-Characterization-of-Furan-Based"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,7,4]]},"references-count":35,"journal-issue":{"issue":"28","published-online":{"date-parts":[[2024,7,4]]},"published-print":{"date-parts":[[2024,7,16]]}},"URL":"https:\/\/doi.org\/10.1021\/acsomega.4c03274","relation":{},"ISSN":["2470-1343"],"issn-type":[{"value":"2470-1343","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,7,4]]}}}