Effect of nature and extent of functional group modification on properties of thermosets from methacrylated epoxidized sucrose soyate

Yu, Arvin Z.; Sahouani, Jonas M.; Setien, Raul A.

doi:10.1016/j.reactfunctpolym.2018.05.003

Cited by 9 publications

(7 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Motivated by a desire to innovate novel and practical solutions, some of our interest in sustainable thermosets has focused on utilizing epoxidized sucrose soyate (ESS) , and its methacrylated derivatives, including dimethacrylated epoxidized sucrose soyate (DMESS). − Notably, the high degree of functionality combined with rigid sucrose core impart high performance in terms of thermomechanical properties to DMESS-based thermosets as compared with traditional soybean oil derived resins. Vinyl ester resins in general are well-known for their robust performance in a variety of applications and are generally more reactive than unsaturated polyester resins due to the substitution pattern of the vinyl moiety .…”

Section: Introductionmentioning

confidence: 99%

Renewable Reactive Diluents as Practical Styrene Replacements in Biobased Vinyl Ester Thermosets

Serum

Renner

et al. 2018

ACS Sustainable Chem. Eng.

Self Cite

View full text Add to dashboard Cite

A concise series of renewable vinyl compounds has been prepared from benign biosourced precursors, vanillin and eugenol, in fair overall yield. These were evaluated against styrene as reactive diluents in a renewable high-performance vinyl ester resin thermoset: dimethacrylated-epoxidized-sucrose-soyate (DMESS). Each diluent contained a 1,2-dimethoxybenzene or veratrole core structure that connotes a decreased vapor pressure and thereby reduced exposure hazard. Viscosities for formulations (10, 20, and 30% by weight of diluents) with styrene and all three veratrole-diluents were evaluated. Veratrole-diluents were comparable to styrene at similar molar concentration. Thermosets formulated with 30% by weight of diluents were prepared and characterized by thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), and dynamic mechanical thermal analysis (DMTA); the most promising thermoset was prepared using 3-allyl-1,2-dimethoxy-5-vinylbenzene-diluted-DMESS and closely matched the performance of the styrene-diluted thermoset in terms of thermal stability, glass transition temperature, toughness, and tensile strength.

show abstract

Section: Introductionmentioning

confidence: 99%

Renewable Reactive Diluents as Practical Styrene Replacements in Biobased Vinyl Ester Thermosets

Serum

Renner

et al. 2018

ACS Sustainable Chem. Eng.

Self Cite

View full text Add to dashboard Cite

show abstract

“…These signals, as observed in prior studies, indicate the presence of oligomers which likely formed due to hydroxyl–epoxy alkoxylation during synthesis. This is more extensive for AESS since there is more hydroxyl content formed during the reaction. − The solid contents of the resins show AESS, MBSS, and ESS to be very high, while DMESS is around 90%. This is most likely due to unreacted methacrylic acid monomer since the reaction was stopped at an acid number of 15 to keep it consistent with the other resins and prevent gelation that could occur at longer reaction times.…”

Section: Resultsmentioning

confidence: 99%

“…AESS (acrylated ESS) is synthesized from the reaction of acrylic acid with ESS where 90% of the epoxy groups are reacted . DMESS (dimethacrylated ESS) is synthesized from the reaction of methacrylic anhydride and methacrylic acid with ESS, where the epoxy and subsequent hydroxyl groups are reacted (2 equiv acid:1 equiv oxirane, with an acid to anhydride molar ratio of 1:9) . MBSS (methacrylated butylated ESS) is synthesized by reacting both methacrylic anhydride and butyric anhydride with ESS where the epoxy and subsequent hydroxyl groups are reacted (2 equiv acid:1 equiv oxirane, with butyric anhydride to methacrylic anhydride molar ratio of 1:9) .…”

Section: Experimental Sectionmentioning

confidence: 99%

Exploration of Bio-Based Functionalized Sucrose Ester Resins for Additive Manufacturing via Stereolithography

Silbert

Simpson

Setien

et al. 2020

ACS Appl. Polym. Mater.

Self Cite

View full text Add to dashboard Cite

Highly functional bio-based methacrylate and acrylate resins were synthesized from epoxidized sucrose soyate (ESS) and incorporated into formulations for stereolithographic (SLA) printing. These formulations were compared to a commercial SLA resin and with formulations where the bioderived resins were replaced with commercial urethane acrylates. The tensile, flexural, rheological, and thermomechanical performances of the respective formulations and their prints were compared. All of the formulations were able to be printed satisfactorily with a Peopoly Moai SLA 3D printer. The acrylated ESS resin showed the highest viscosity while the methacrylated ESS resins had lower viscosities than the control urethane acrylates. The prints made from the formulations containing the methacrylated ESS resins had similar T g s to that of the urethane acrylate control formulations while the prints from the acrylated ESS resin had a lower T g . The tensile and flexural properties were consistent with the T g values in terms of modulus, but some of the prints showed surface cracking that compromised the strength properties. This study demonstrated the ability of a bio-derived material to be functionally modified and incorporated into an SLA formulation and printed in different orientations.

show abstract

“…The Webster group has extensively researched the many different applications of this type of molecule and its functional derivatives in comparison to other vegetable-oil-based starting materials. 20,21,[26][27][28][29] Traditionally, these epoxidized vegetable-oil-based resins are synthesized using a peracid generated in situ to undergo epoxidation. 30 This process includes the use of hydrogen peroxide, an ion exchange resin and acetic acid in order to generate peracid, which is then used to convert unsaturated sites into oxirane rings (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

“…The sucrose core along with the highly branched long carbon chain structure gives sucrose soyate unique mechanical properties compared to soybean oil. The Webster group has extensively researched the many different applications of this type of molecule and its functional derivatives in comparison to other vegetable‐oil‐based starting materials 20,21,26–29 …”

Section: Introductionmentioning

confidence: 99%

Comparison of epoxidation methods for biobased oils: dioxirane intermediates generated from Oxone versus peracid derived from hydrogen peroxide

Setien

Ghasemi

Pourhashem

2021

Polymer International

View full text Add to dashboard Cite

A study was carried out to compare the epoxidation of unsaturated vegetable oils using dioxirane intermediates generated in situ using Oxone to that by the peracid/hydrogen peroxide method. Epoxidized oils are typically synthesized using hydrogen peroxide, as well as acetic or formic acid. This synthesis requires heating and catalysts and generates acidic waste. Recently, advances have been made in the process of using Oxone (potassium peroxymonosulfate) and ketones to generate in situ dioxiranes to epoxidize alkenes. The dioxirane method allows for room temperature reactions and eliminates the use of peroxides and acids. Epoxidation of soybean oil, hempseed oil and sucrose soyate using in situ generated dioxiranes was carried out and parameters such as molar ratios and addition rates were studied. The data show that optimum reaction conditions are reached when molar ratios of Oxone and unsaturation are 1.6:1 and the Oxone addition rate is 1 mL min -1 . As a comparison, epoxidations using the acetic acid/hydrogen peroxide method were carried out and cured materials were prepared from the epoxidized compounds. Negligible differences were identified in the materials prepared from both synthetic pathways. An environmental sustainability assessment using green chemistry principles was also conducted for both methods to evaluate their safety and efficiency with respect to multiple criteria including minimizing waste generation and energy consumption. The analysis shows that, although the peracid method is atom economic and generates less waste, the dioxirane method offers better occupational safety and requires less energy, demonstrating the tradeoffs involved with either pathway if one is to be selected.

show abstract

Effect of nature and extent of functional group modification on properties of thermosets from methacrylated epoxidized sucrose soyate

Cited by 9 publications

References 36 publications

Renewable Reactive Diluents as Practical Styrene Replacements in Biobased Vinyl Ester Thermosets

Renewable Reactive Diluents as Practical Styrene Replacements in Biobased Vinyl Ester Thermosets

Exploration of Bio-Based Functionalized Sucrose Ester Resins for Additive Manufacturing via Stereolithography

Comparison of epoxidation methods for biobased oils: dioxirane intermediates generated from Oxone versus peracid derived from hydrogen peroxide

Contact Info

Product

Resources

About