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Polythionourethane Thermoset Synthesis via Activation of Elemental Sulfur in an Efficient Multicomponent Reaction Approach
Institute of Organic Chemistry (IOC), Materialwissenschaftliches Zentrum MZE, Karlsruhe Institute of Technology (KIT), Straße am Forum 7, 76131 Karlsruhe, Germany, Straße am Forum 7.
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology. KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Centres, Wallenberg Wood Science Center.ORCID iD: 0000-0002-8127-9183
Institute of Organic Chemistry (IOC), Materialwissenschaftliches Zentrum MZE, Karlsruhe Institute of Technology (KIT), Straße am Forum 7, 76131 Karlsruhe, Germany, Straße am Forum 7; Institute of Biological and Chemical Systems − Functional Molecular Systems (IBCS-FMS), Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany, Hermann-von-Helmholtz-Platz 1.ORCID iD: 0000-0002-4448-5279
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology. KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Centres, Wallenberg Wood Science Center.ORCID iD: 0000-0003-3201-5138
2023 (English)In: ACS Sustainable Chemistry and Engineering, E-ISSN 2168-0485, Vol. 11, no 9, p. 3952-3962Article in journal (Refereed) Published
Abstract [en]

For the transition toward a safer and more sustainable production of polymeric materials, new synthetic concepts need to be developed. Herein, we describe a catalytic, solvent-free synthesis approach for novel thionourethane thermoset materials, in which the diisothiocyanate reactant is generated in situ via a sulfurization of isocyanides with elemental sulfur, preventing the exposure and handling of the diisothiocyanate. In this one-pot procedure, castor oil fulfills a dual role: (i) acting as the solvent for the in situ diisothiocyanate synthesis in the first step and (ii) reacting as the polyol component in the subsequent thionourethane thermoset formation. The kinetics of the consecutive two steps were studied in detail via real-time IR measurements, and the thermoset crosslinking step was found to be thermally triggerable after the diisothiocyanate reactant is quantitatively formed, enabling high control over the curing process of the system. Differential scanning calorimetry, thermogravimetric analysis, and rheological measurements were performed to investigate the thermal and mechanical properties of the novel thionourethane thermosets and then compared to analogous polyurethane materials. Our results demonstrate an unprecedented approach for thermoset synthesis via an in situ reagent synthesis, i.e., the generation of isothiocyanates from isocyanides by catalytic activation of elemental sulfur, and subsequent thermally triggerable thermosetting with a polyol, resulting in materials with appealing properties.

Place, publisher, year, edition, pages
American Chemical Society , 2023. Vol. 11, no 9, p. 3952-3962
Keywords [en]
castor oil, DBU, isocyanide, isothiocyanate, multicomponent reaction, organocatalysis, sulfur, thermoset, thiourethane
National Category
Polymer Chemistry Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-330957DOI: 10.1021/acssuschemeng.3c00143ISI: 000935519600001Scopus ID: 2-s2.0-85148872086OAI: oai:DiVA.org:kth-330957DiVA, id: diva2:1781245
Note

QC 20230707

Available from: 2023-07-07 Created: 2023-07-07 Last updated: 2023-07-07Bibliographically approved

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Ribca, IulianaJohansson, Mats

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Ribca, IulianaMeier, Michael A.R.Johansson, Mats
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