Soybean oil based thermoset networks via photoinduced CuAAC click chemistry

• Published in: Polymer international 2017-07, Vol.66 (7), p.999-1004
• Main Authors: Uysal, Naci, Acik, Gokhan, Tasdelen, Mehmet Atilla
• Format: Article
• Language: English
• Subjects: Alkynes; Chemical industry; Chemical reactions; Chemical synthesis; click chemistry; Copper; copper‐catalyzed azide − alkyne cycloaddition; Crosslinking; Cycloaddition; Damping; Density; Formulations; Glass transition temperature; Mechanical properties; Monomers; Networks; photochemistry; Propargyl alcohol; Renewable resources; Sodium; Sodium azide; Soybean oil; Soybeans; Storage modulus; Sustainable yield; Temperature effects; thermosets; Thermosetting resins; vegetable oil; Vegetable oils
• ISSN: 0959-8103; 1097-0126
• DOI: 10.1002/pi.5346

A simple method based on photochemically induced copper(I)‐catalyzed azide − alkyne cycloaddition click reaction (CuAAC) is developed for the preparation of thermoset networks from soybean oils as renewable resources. The incorporation of clickable azide and alkyne functionalities into epoxidized soybean oils is done by simultaneous ring‐opening reactions between the epoxide group of soybean oils and sodium azide and propargyl alcohol, respectively. The obtained azide‐ and alkyne‐functionalized soybean oils are easily transformed crosslinked networks via the photoinduced CuAAC reaction in ambient conditions. The introduction of additional multifunctional monomers in the formulation not only increases the crosslinking density but also improves the mechanical properties of the thermoset material obtained. In a comparison of the two formulations, the sample containing additional multifunctional monomers has a higher glass transition temperature, storage modulus and damping properties. © 2017 Society of Chemical Industry Soybean oil based thermoset was successfully prepared by photoinduced CuAAC click reaction under mild conditions using azide‐ and alkyne‐functional precursors in the presence of DMPA/CuBr2/PMDETA as catalyst. The highly crosslinked thermoset formations are primarily confirmed by FTIR spectroscopy. The samples obtained have higher thermal and mechanical properties such as glass transition temperature, storage modulus and damping properties.