Thiourethane thermoset coatings from bio-based thiols

Abstract

Three bio-based thiols were synthesized via the thermal thiol-ene reactions between sucrose soya ester (SSE) and multifunctional thiols; then, thiourethane coatings were produced from these thiols and their coating properties were studied. A series of high bio-renewable content thiol oligomers were synthesized according to the previously reported thermal thiol-ene reaction. Fourier transform infrared spectra (FTIR) confirmed the complete consumption of the double bonds in SSE, and gel permeation chromatography confirmed the formation of high-molecular-weight oligomers. The viscosity of these oligomers remained low due to their compact and branched structures. Thermoset thiourethane coatings were prepared from these thiol oligomers and polyisocyanate trimer resins with dibutyltin diacetate as the catalyst. FTIR spectra confirmed the formation of the thiourethane group. However, coatings based on isophorone diisocyanate (IPDI) polyisocyanate resin showed a lower degree of cure because of the decreased resin mobility due to the rigid cyclohexane ring. Generally, all the coatings showed good adhesion to aluminum panels, and had high gloss. However, they exhibited low tensile strength, modulus and chemical resistance due to the flexibility of the fatty acid chain. Coatings based on more rigid IPDI-based polyisocyanate showed higher T g, hardness and direct impact resistance compared with the hexamethylene-diisocyanate (HDI) based polyisocyanate counterparts. Thermogravimetric analysis results showed that coatings based on mercaptanized soybean oil have better thermal stability than those from di-pentene dimercaptan or glycol di-3-mercaptopropionate. Two T g values were found by both differential scanning calorimetry and dynamic mechanical thermal analysis of thiourethanes from HDI-based polyisocyanate and di-pentene dimercaptan or glycol di-3-mercaptopropionate based oligomers due to phase separation resulting from the poor compatibility between HDI-based polyisocyanate and the respective oligomers. Three bio-based thiols were synthesized based on the thermal thiol-ene reactions between sucrose soya ester (SSE) and multifunctional thiols; then, thiourethane coatings were produced from these bio-based thiols and their coating properties were studied. © 2011 Society of Chemical Industry.