Reactive Diluent Derived from Ferulic Acid for the Preparation of a Fully Biobased Unsaturated Polyester Resin

Abstract

A reactive diluent for the preparation of a fully biobased unsaturated polyester resin (UPR) was developed and is presented here. The diluent, 4-vinylguaiacol acetyl ester (AC4VG), was obtained via a simple two-step synthesis: decarboxylation from ferulic acid (FA) and acetylation of the decarboxylated product, 4-vinylguaiacol (4VG). This diluent shows excellent miscibility with biobased unsaturated polyester prepolymer (UPP) that had been synthesized from succinic acid (SA), 1,3-dihydroxypropane (PD), and itaconic acid (IA). A mixed solution of these possessed a very low viscosity at 174 mPa·s at room temperature when 40 wt% AC4VG was added. Moreover, its vinyl group brought high reactivity for free radical copolymerization with the UPP, and the benzene ring structure enabled a high glass transition temperature (T g) of the cured UPR. When the fully biobased UPR was reinforced by cotton fabric, a strong tensile strength at the break of approximately 65.8 MPa, a T g of 135 °C, and a T d5% of 276 °C were achieved. This work suggests that the fully biobased UPR reported here is a promising candidate for replacing petroleum-based ones, and the diluent AC4VG played an important role in the performance of this biobased UPR.

Highly Bio‐Based Unsaturated Polyester Resins with Improved Performance by Incorporating Isosorbide into the Polyester Prepolymer

“…These resins start thermal degradation at ≈250 °C, and reach the maximum decomposition rates at ≈400 °C. Further, these resins exhibit higher T d5% and R 600 values shown in Tables S4 and S5 (Supporting Information) when compared to the previous works, [ 25,61,63,64 ] this is mainly attributed to the ISO monomer used to prepare the UPs. Among the four resins, the highest T d5% of 320 °C was obtained at the ACVG/PIOSE20 resin, which can be explained by its highest gel content and highest content of the isosorbide units.…”

“…Synthesis of Acetylated 2-Methoxy-4-Vinylphenol (ACVG): As reactive monomer for the cross-linking of the bio-based UPs, ACVG was synthesized according to a cross linking of the bio-based UPs, ACVG was synthesized according to a previous work. [25] Briefly, FA was decarboxylated at 100 °C to obtain 4-vinylphenol (VG), then acylated with acetic anhydride to obtain the active diluent acetylated 2-methoxy-4-vinylphenol (ACVG) as shown in Figure S2 (Supporting Information).…”

“…With increasing environmental concerns on both the depletion of petroleum source and the burdensome waste treatment, design, and synthesize of renewable polymers have been presented as a new development direction of polymer chemistry. [1][2][3][4][5] After successful commercialization of several bio-based thermoplastics such as polylactic acid (PLA), [6,7] polyhydroxyalkanoates DOI: 10.1002/mame.202200203 (PHA), [8,9] and polybutylene succinate (PBS), [10] polymerization of bio-based thermosetting resins like epoxy resins, [11,12] furan resins, [13,14] benzoxazine resins, [15][16][17][18][19][20][21] urea-formaldehyde resins, [22,23] and unsaturated polyester resins (UPRs) [24,25] have been reported extensively.…”

“…Previously, we developed a polymerizable diluent, 4‐vinylguaiacol acetyl ester (ACVG), through a green route sourcing from ferulic acid. [ 25 ] This diluent was very miscible with the UP that obtained from succinic acid, 1, 3‐dihydroxypropane and IA. The ACVG/UP mixture was demonstrated to be a promising combination for preparing highly bio‐based thermosetting.…”

Preparation of SnO2‐Based Composite Gas‐Sensitive Material and Its Effect on the Membrane Treatment Process of Volatile Organic Compounds

“…In order to explore the pollution mechanism of ultrafiltration under different pretreatment conditions, the experiment refers to the Darcy resistance model [11] and analyzes each part of the resistance generated during the ultrafiltration process. The formula is as follows:…”