Making vinyl ester resin greener: Succinic acid–glycerol‐derived reactive diluent as an alternative to styrene

Abstract

A bio‐based reactive diluent (BRD) was synthesized from succinic acid and glycerol, and successfully copolymerized with epoxy acrylate (EA). Chemical structure of BRD was studied by nuclear magnetic resonance and Fourier transform infrared. The performance of vinyl ester resin compositions has been examined through differential scanning calorimetry, thermogravimetric analysis, and dynamic mechanical analysis, as well as tensile and flexural tests. Results demonstrated good compatibility between EA and the BRD. Compared to styrene, the BRD contribution of 50 wt% enhanced the elastic modulus (~40%). Samples copolymerized with BRD or styrene, have shown a similar thermal stability. Mechanical properties of cured blends, containing up to 25 wt% of BRD, found to be superior than styrene‐diluted compartments. Viscosities of EA–BRD blends were in range of 3.25–0.43 Pa/s at 30°C. Inexpensive bio‐based source, good thermomechanical and rheological properties, and great compatibility with EA are of advantages of these BRD‐containing formulations.

Quick and green toward conductive thermally‐stable biobasedstar‐shapedoligomers

“…The SSB structure have additionally been investigated (Figure 2B) and peaks were assigned based on former studies 15,17,56 : the broad peak between 2800–3460 cm −1 is assigned to the OH stretching of the hydroxyl groups of the carboxylic acid‐available functional groups on succinate arms and the transmittance of CH 2 (of succinic acid) and CH (of glycerol) bonds(stretching vibrations) between 2900 and 3000 cm −1 can deform the broad band into multiple peak signal; the left shoulder on hydroxyl band at 3460 cm −1 is assigned to the alcohol hydroxyl group of the short arm of SSB; the carbonyl stretched band (CO) has presented a peak at 1737 cm −1 and a right shoulder at 1720 cm −1 which are related to the ester and acid groups, respectively. Two signals at 1210–1320 and the strong peak at 1160 cm −1, is related to the stretching of CO and COC groups.…”

“…Also peak at 3.9 ppm (marked as D) can be attributed to the methine of glycerol, and the methylene protons of succinic acid is appeared at 2.48 ppm (marked as E) near the peak of DMSO at 2.5 ppm. As glycerol has three hydroxyl groups, two secondary and one primary, more likely due to less steric hindrance the primary hydroxyls are more reactive than the secondary ones, although it cannot be generalized 17 . Therefore, based on this possibility that the primary hydroxyls have more reactivity, in the presence of 2 equiv of succinic acid it is considered that two primary hydroxyls react with this 2 equiv of succinic acid.…”

“…[11][12][13] The nature of core molecule, length of arms, architecture of the network, and method used for end-functionalization are directly affect properties of resin. 14 Hydrophilic multi-hydroxyl core molecules, including glycerol, xylitol, ethylene glycol, and erythritol were used for different applications, 15 whereas dicarboxylic acids, such as succinic acid, [15][16][17] lactic acid, 11,12,18,19 and itaconic acid, 13,20 were used as arms. Succinic acid and glycerol are biobased molecules, considered as members of the list of the 12 building block chemicals by the US department of Energy, which are producible from renewable raw resource via bioconversion or chemical production to deal with the shortage of petroleum-based resource.…”

Low volatile monofunctional reactive diluents for radiation curable formulations

“…Recently, Palmese et al modified plant‐based carvacrol, thymol, and menthol with methacrylates and successfully used them as reactive dilutents for vinyl ester thermosetting resins 12 . Another approach was the synthesis of new succinic acid‐glycerol derived thinners 13 …”

Functional Properties of Kenaf Bast Fibre Anhydride Modification Enhancement with Bionanocarbon in Polymer Nanobiocomposites

“…On the other hand, vinyl ester has been widely utilised for liquid-moulding formulations due to its low weight, good chemical resistance, low cost, high toughness, low volume shrinkage, and low exothermal heat [ 19 ]. Consequently, it has been employed in many industrial-scale applications such as coatings, adhesives, structural laminates, military/aerospace, surface vehicles, moulding compounds, and automobile parts [ 20 ]. However, a neat composite of the vinyl ester is brittle.…”