Synthesis and Copolymerization of Fully Biobased Benzoxazines from Renewable Resources

Abstract

A solventless method was adopted to synthesize two benzoxazine monomers from naturally occurring sources, i.e., eugenol (an extraction from clove), furfurylamine, stearylamine, and paraformaldehyde. The structure of the extracted eugenol and synthesized monomers were supported by FT-IR, 1 H NMR, 13 C NMR, and mass spectral analysis. The monomers were polymerized/copolymerized via ring-opening polymerization by heating as shown by FT-IR (disappearance of the peak due to oxazine ring at 920 cm −1 ) and differential scanning colorimetry (DSC). The exothermic peak associated with curing was observed between 198−254 °C. DSC analysis shows that the onset of curing temperature for the copolymers decreased linearly from 207−202 °C on increasing the content of F-Bz. The results from TGA analysis indicate that PF-Bz shows the maximum thermal stability when compared with PS-Bz and their copolymers. In the case of the copolymers, as the F-Bz content is increased, the thermal stability also increases. All the polymers also exhibit good flame retardant properties as shown by their LOI values (more than 26).

Biobased Benzoxazine Derived from Daidzein and Furfurylamine: Microwave‐Assisted Synthesis and Thermal Properties Investigation

“…[15] Up to now,alarge quantity of biobased benzoxazines have already been prepared from the renewable cardanol, [16,17] diphenolic acid, [18,19] phloretic acid, [20] furfurylamine, [21,22] stearylamine, [23] coumarin, [24,25] umbelliferone, [26] and more recently the lignin derivatives (guaiacol, [27][28][29][30] vanillin, [31][32][33] and eugenol [34][35][36][37][38] ). [15] Up to now,alarge quantity of biobased benzoxazines have already been prepared from the renewable cardanol, [16,17] diphenolic acid, [18,19] phloretic acid, [20] furfurylamine, [21,22] stearylamine, [23] coumarin, [24,25] umbelliferone, [26] and more recently the lignin derivatives (guaiacol, [27][28][29][30] vanillin, [31][32][33] and eugenol [34][35][36]…”

From a bio-based phosphorus-containing epoxy monomer to fully bio-based flame-retardant thermosets

“…Among additives, ame retardants (FR) represent a signicant group whose use is crucial in many sectors where re safety is a major issue (building, transportation, electronics.). 20 Up to now, there have been only a limited number of papers reporting bio-based solutions for epoxy ame retardancy. 9 One promising way consists in preparing FR from renewable resources.…”

Bio‐based benzoxazines based on sesamol: Synthesis and properties

“…bio-based benzoxazines by Ishida, who found that monomers based on coumarin are photopolymerizable and that the surfaces of corresponding polymers have good hydrophobicity. 31 Cádiz synthesized a series of tough benzoxazine resins using castor oil, 32 and eugenol was used to synthesize a series of bio-based benzoxazines and composite materials by Thirukumaran et al 33 Furfurylamine and stearylamine are widely used by researcher to synthesize fully bio-based benzoxazines. It has been reported that furan ring structures can participate in benzoxazine crosslinking reactions and improve the crosslinking density of the system.…”