Ivan Hevus, Sandip Tiwari, Sagar Thorat, Luke R. Gibbon, John J. La Scala, Chad A. Ulven, Mukund P. Sibi and Dean C. Webster*,
{"title":"立体光刻中的香兰素衍生维拉特罗反应稀释剂","authors":"Ivan Hevus, Sandip Tiwari, Sagar Thorat, Luke R. Gibbon, John J. La Scala, Chad A. Ulven, Mukund P. Sibi and Dean C. Webster*, ","doi":"10.1021/acsapm.4c01183","DOIUrl":null,"url":null,"abstract":"<p >We demonstrated the applicability of two vanillin-derived veratrole monomers, 4-vinyl veratrole (VV) and 3-allyl-5-vinyl veratrole (AVV), as reactive diluents for stereolithography (SLA). As structural analogues of styrene, these nonvolatile biobased monomers enable expanding the applications of styrenics to photocurable systems. Both monomers reduced the viscosity of a commercial oligomeric urethane acrylate resin to the levels acceptable for high-resolution SLA three-dimensional (3D) printing. Compared to two petrochemical controls, 2-phenoxyethyl acrylate and <i>N</i>-vinylpyrrolidone, the veratrole monomers required higher laser exposure to polymerize but allowed achieving high conversion of styrenic double bonds in the SLA process. Participation of the allyl group of AVV in polymerization increased the cross-link density of the 3D printed material, resulting in improved thermal stability and strength characteristics, whereas the VV-containing formulation yielded samples with superior ductility and toughness. Both vanillin-derived monomers demonstrated a significant advantage over 2-phenoxyethyl acrylate, a commercial aromatic diluent, in the thermomechanical properties of the printed materials. Furthermore, VV-based materials had higher elongation at break than the high-performing <i>N</i>-vinylpyrrolidone-containing formulation, whereas AVV showed superior Young’s modulus. We expect that the performance demonstrated by the veratrole monomers will accelerate the introduction of biobased styrenics into SLA resin formulations.</p>","PeriodicalId":7,"journal":{"name":"ACS Applied Polymer Materials","volume":null,"pages":null},"PeriodicalIF":4.4000,"publicationDate":"2024-06-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Vanillin-Derived Veratrole Reactive Diluents in Stereolithography\",\"authors\":\"Ivan Hevus, Sandip Tiwari, Sagar Thorat, Luke R. Gibbon, John J. La Scala, Chad A. Ulven, Mukund P. Sibi and Dean C. Webster*, \",\"doi\":\"10.1021/acsapm.4c01183\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >We demonstrated the applicability of two vanillin-derived veratrole monomers, 4-vinyl veratrole (VV) and 3-allyl-5-vinyl veratrole (AVV), as reactive diluents for stereolithography (SLA). As structural analogues of styrene, these nonvolatile biobased monomers enable expanding the applications of styrenics to photocurable systems. Both monomers reduced the viscosity of a commercial oligomeric urethane acrylate resin to the levels acceptable for high-resolution SLA three-dimensional (3D) printing. Compared to two petrochemical controls, 2-phenoxyethyl acrylate and <i>N</i>-vinylpyrrolidone, the veratrole monomers required higher laser exposure to polymerize but allowed achieving high conversion of styrenic double bonds in the SLA process. Participation of the allyl group of AVV in polymerization increased the cross-link density of the 3D printed material, resulting in improved thermal stability and strength characteristics, whereas the VV-containing formulation yielded samples with superior ductility and toughness. Both vanillin-derived monomers demonstrated a significant advantage over 2-phenoxyethyl acrylate, a commercial aromatic diluent, in the thermomechanical properties of the printed materials. Furthermore, VV-based materials had higher elongation at break than the high-performing <i>N</i>-vinylpyrrolidone-containing formulation, whereas AVV showed superior Young’s modulus. We expect that the performance demonstrated by the veratrole monomers will accelerate the introduction of biobased styrenics into SLA resin formulations.</p>\",\"PeriodicalId\":7,\"journal\":{\"name\":\"ACS Applied Polymer Materials\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.4000,\"publicationDate\":\"2024-06-26\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"ACS Applied Polymer Materials\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acsapm.4c01183\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"MATERIALS SCIENCE, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Applied Polymer Materials","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acsapm.4c01183","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"MATERIALS SCIENCE, MULTIDISCIPLINARY","Score":null,"Total":0}
Vanillin-Derived Veratrole Reactive Diluents in Stereolithography
We demonstrated the applicability of two vanillin-derived veratrole monomers, 4-vinyl veratrole (VV) and 3-allyl-5-vinyl veratrole (AVV), as reactive diluents for stereolithography (SLA). As structural analogues of styrene, these nonvolatile biobased monomers enable expanding the applications of styrenics to photocurable systems. Both monomers reduced the viscosity of a commercial oligomeric urethane acrylate resin to the levels acceptable for high-resolution SLA three-dimensional (3D) printing. Compared to two petrochemical controls, 2-phenoxyethyl acrylate and N-vinylpyrrolidone, the veratrole monomers required higher laser exposure to polymerize but allowed achieving high conversion of styrenic double bonds in the SLA process. Participation of the allyl group of AVV in polymerization increased the cross-link density of the 3D printed material, resulting in improved thermal stability and strength characteristics, whereas the VV-containing formulation yielded samples with superior ductility and toughness. Both vanillin-derived monomers demonstrated a significant advantage over 2-phenoxyethyl acrylate, a commercial aromatic diluent, in the thermomechanical properties of the printed materials. Furthermore, VV-based materials had higher elongation at break than the high-performing N-vinylpyrrolidone-containing formulation, whereas AVV showed superior Young’s modulus. We expect that the performance demonstrated by the veratrole monomers will accelerate the introduction of biobased styrenics into SLA resin formulations.
期刊介绍:
ACS Applied Polymer Materials is an interdisciplinary journal publishing original research covering all aspects of engineering, chemistry, physics, and biology relevant to applications of polymers.
The journal is devoted to reports of new and original experimental and theoretical research of an applied nature that integrates fundamental knowledge in the areas of materials, engineering, physics, bioscience, polymer science and chemistry into important polymer applications. The journal is specifically interested in work that addresses relationships among structure, processing, morphology, chemistry, properties, and function as well as work that provide insights into mechanisms critical to the performance of the polymer for applications.