Network polymers containing disulfide bond prepared by addition reactions of multi-functional epoxies, aziridine, or isocyanates with dicarboxylic acids or diols: structure, mechanical properties, and reductive degradation

Network polymers containing disulfide bond prepared by addition reactions of multi-functional epoxies, aziridine, or isocyanates with dicarboxylic acids or diols: structure, mechanical properties, and reductive degradation | 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 Network polymers containing disulfide bond prepared by addition reactions of multi-functional epoxies, aziridine, or isocyanates with dicarboxylic acids or diols: structure, mechanical properties, and reductive degradation Naofumi Naga, Kazumasa Moriyama, Kazuma Hasegawa, Toshiki Tajima, and 1 more This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-7874491/v1 This work is licensed under a CC BY 4.0 License Status: Published Journal Publication published 26 Feb, 2026 Read the published version in Journal of Polymer Research → Version 1 posted 5 You are reading this latest preprint version Abstract Network polymers containing disulfide bonds were synthesized through ring-opening addition reactions of multi-functional epoxides or a tri-aziridine with dithiodicarboxylic acids. Reactions of tri- or tetra-functional epoxide, namely tris(4-hydroxyphenyl) methane triglycidyl ether (TME) and tetraphenylolethane glycidyl ether (TPE), with dithiodicarboxylic acids of varying methylene chain length, dithiodiglycolic acid (DTGA), 3,3'-dithiodipropionic acid (DTPA), or 4,4'-dithiodibutyric acid (DTBA), in the presence of tetrabutylammonium bromide in dimethyl sulfoxide (DMSO) at 85 ºC afforded the corresponding gels. Gels prepared from DTBA exhibited an enhanced Young’s modulus, attributed to the high extent of reaction conversion. These gels underwent reductive degradation upon immersion in a DMSO solution of dithiothreitol (DTT), while subsequent heating of the resulting solutions regenerated the gel structures through oxidation mediated by DMSO. Ring-opening addition reaction of tri-aziridine, 2,2-bishydroxymethylbutanol-tris[3-(1-aziridinyl)propionate] (3AZ) with dithiodicarboxylic acids in methanol successfully yielded porous polymers via polymerization induced phase separation (PIPS). The resulting materials exhibited porous morphologies composed of interconnected particles with diameters ranging from approximately 1 to 4 µm. The particle size increased with the alkyl length of the dithiodicarboxylic acid, concomitant with a reduction in the Young’s modulus of the porous polymers. In addition, the reaction of tri-functional isocyanate, 1,3,5-Tris[6-(isocyanate)hexyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (3I) with bis(2-hydroxyethyl) disulfide (HEDS) or DTGA in DMSO produced the corresponding gels. These gels were susceptible to reductive degradation in DMSO solutions of DTT, and notably, the 3I-HEDS gel was degradable under electrochemical reduction. The reaction of 3I with DTGA in tetrahydrofuran (THF) afforded porous polymers exhibiting co-continuous monolithic morphologies consisting of interconnected particles. The morphology was tunable by varying concentration of triethylamine employed as a catalyst. The 3I-DTGA porous polymer likewise underwent reductive degradation upon immersion in THF solution of DTT. gel porous polymer disulfide bond degradation Full Text Supplementary Files SSnetworkfinalSI.docx Cite Share Download PDF Status: Published Journal Publication published 26 Feb, 2026 Read the published version in Journal of Polymer Research → Version 1 posted Reviewers agreed at journal 05 Nov, 2025 Reviewers invited by journal 05 Nov, 2025 Editor invited by journal 26 Oct, 2025 Editor assigned by journal 17 Oct, 2025 First submitted to journal 16 Oct, 2025 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. As a division of Research Square Company, we’re committed to making research communication faster, fairer, and more useful. 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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-7874491","acceptedTermsAndConditions":true,"allowDirectSubmit":false,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":540214895,"identity":"5a461a5c-5421-4b0f-8185-2f278877a623","order_by":0,"name":"Naofumi 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degradation","fulltext":[],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":false,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":false,"hideJournal":false,"highlight":"","institution":"","isAcceptedByJournal":true,"isAuthorSuppliedPdf":true,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":true,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"journal-of-polymer-research","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"jpol","sideBox":"Learn more about [Journal of Polymer Research](https://www.springer.com/journal/10965)","snPcode":"10965","submissionUrl":"https://www.editorialmanager.com/jpol/","title":"Journal of Polymer Research","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false},"keywords":"gel, porous polymer, disulfide bond, degradation","lastPublishedDoi":"10.21203/rs.3.rs-7874491/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-7874491/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eNetwork polymers containing disulfide bonds were synthesized through ring-opening addition reactions of multi-functional epoxides or a tri-aziridine with dithiodicarboxylic acids. Reactions of tri- or tetra-functional epoxide, namely tris(4-hydroxyphenyl) methane triglycidyl ether (TME) and tetraphenylolethane glycidyl ether (TPE), with dithiodicarboxylic acids of varying methylene chain length, dithiodiglycolic acid (DTGA), 3,3'-dithiodipropionic acid (DTPA), or 4,4'-dithiodibutyric acid (DTBA), in the presence of tetrabutylammonium bromide in dimethyl sulfoxide (DMSO) at 85 \u0026ordm;C afforded the corresponding gels. Gels prepared from DTBA exhibited an enhanced Young\u0026rsquo;s modulus, attributed to the high extent of reaction conversion. These gels underwent reductive degradation upon immersion in a DMSO solution of dithiothreitol (DTT), while subsequent heating of the resulting solutions regenerated the gel structures through oxidation mediated by DMSO. Ring-opening addition reaction of tri-aziridine, 2,2-bishydroxymethylbutanol-tris[3-(1-aziridinyl)propionate] (3AZ) with dithiodicarboxylic acids in methanol successfully yielded porous polymers via polymerization induced phase separation (PIPS). The resulting materials exhibited porous morphologies composed of interconnected particles with diameters ranging from approximately 1 to 4 \u0026micro;m. The particle size increased with the alkyl length of the dithiodicarboxylic acid, concomitant with a reduction in the Young\u0026rsquo;s modulus of the porous polymers. In addition, the reaction of tri-functional isocyanate, 1,3,5-Tris[6-(isocyanate)hexyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (3I) with bis(2-hydroxyethyl) disulfide (HEDS) or DTGA in DMSO produced the corresponding gels. These gels were susceptible to reductive degradation in DMSO solutions of DTT, and notably, the 3I-HEDS gel was degradable under electrochemical reduction. The reaction of 3I with DTGA in tetrahydrofuran (THF) afforded porous polymers exhibiting co-continuous monolithic morphologies consisting of interconnected particles. The morphology was tunable by varying concentration of triethylamine employed as a catalyst. The 3I-DTGA porous polymer likewise underwent reductive degradation upon immersion in THF solution of DTT.\u003c/p\u003e","manuscriptTitle":"Network polymers containing disulfide bond prepared by addition reactions of multi-functional epoxies, aziridine, or isocyanates with dicarboxylic acids or diols: structure, mechanical properties, and reductive degradation","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2025-11-14 14:34:29","doi":"10.21203/rs.3.rs-7874491/v1","editorialEvents":[{"type":"communityComments","content":0},{"type":"reviewerAgreed","content":"","date":"2025-11-05T11:34:26+00:00","index":0,"fulltext":""},{"type":"reviewersInvited","content":"","date":"2025-11-05T07:19:04+00:00","index":"","fulltext":""},{"type":"editorInvited","content":"Journal of Polymer Research","date":"2025-10-26T19:43:41+00:00","index":"","fulltext":""},{"type":"editorAssigned","content":"","date":"2025-10-17T04:07:04+00:00","index":"","fulltext":""},{"type":"submitted","content":"Journal of Polymer Research","date":"2025-10-16T23:32:18+00:00","index":"","fulltext":""}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"journal-of-polymer-research","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"jpol","sideBox":"Learn more about [Journal of Polymer Research](https://www.springer.com/journal/10965)","snPcode":"10965","submissionUrl":"https://www.editorialmanager.com/jpol/","title":"Journal of Polymer Research","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"em","reportingPortfolio":"Springer Hybrid","inReviewEnabled":true,"inReviewRevisionsEnabled":false}}],"origin":"","ownerIdentity":"76c5b6af-76c1-4782-8881-d0a4c2fcf5a5","owner":[],"postedDate":"November 14th, 2025","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"published-in-journal","subjectAreas":[],"tags":[],"updatedAt":"2026-03-02T16:10:26+00:00","versionOfRecord":{"articleIdentity":"rs-7874491","link":"https://doi.org/10.1007/s10965-026-04811-y","journal":{"identity":"journal-of-polymer-research","isVorOnly":false,"title":"Journal of Polymer Research"},"publishedOn":"2026-02-26 15:57:22","publishedOnDateReadable":"February 26th, 2026"},"versionCreatedAt":"2025-11-14 14:34:29","video":"","vorDoi":"10.1007/s10965-026-04811-y","vorDoiUrl":"https://doi.org/10.1007/s10965-026-04811-y","workflowStages":[]},"version":"v1","identity":"rs-7874491","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-7874491","identity":"rs-7874491","version":["v1"]},"buildId":"8U1c8b4HqxoKbykW_rLl7","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}