Green and Efficient Modification of Grape Seed Oil to Synthesize Renewable Monomers

Gaglieri, Caroline; Alarcon, Rafael Turra; Moura, Aniele de; Magri, Raquel; Silva‐Filho, Luiz Carlos da; Bannach, Gilbert

doi:10.21577/0103-5053.20210104

Cited by 9 publications

(22 citation statements)

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“…However, no exothermic event was observed in both cooling stages. A possible explanation could be that the material is too viscous and slowly solidifies during the cooling process, releasing low amounts of heat which were undetectable via DSC equipment [25]. This was further confirmed by the broad signals between 20 and -15 °C in the first cooling stage and between 15 and -20 °C in the second cooling stage.…”

Section: Uv-vis Liquid State Analysis and Amwo Photolysismentioning

confidence: 79%

A new acrylated monomer from macaw vegetable oil that polymerizes without external photoinitiators

et al. 2021

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The photopolymerization process has been widely studied due to its use in painting/coating, dentistry, creating photoresist materials and more recently in 3D printing. Therefore, new monomers have been synthesized to be used in this growing area. Here, a new Brazilian biomass derived, renewable monomer from macaw vegetable oil is presented. This monomer can self-polymerize without photoinitiation under UV light, reaching a monomer conversion of 75% and a conversion of 88% when ethyl 4-(dimethylamino)benzoate is present as a coinitiator. Furthermore, the final polymer has an orange color under visible light and exhibits fluorescence (a blue color) under UV radiation. Monomers and polymers formed from macaw vegetable oil are thermally stable up to 220 °C, as evidenced by thermogravimetry (TG). The polymers formed also exhibited a glass transition temperature of 2.6 °C, as observed in differential scanning calorimetry (DSC) curves and dynamic-mechanical analysis (DMA). This new monomer presents an alternative monomer to be used in 3D printing, in a similar manner to other vegetable oils such as soybean and linseed.

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Section: Uv-vis Liquid State Analysis and Amwo Photolysismentioning

confidence: 79%

A new acrylated monomer from macaw vegetable oil that polymerizes without external photoinitiators

et al. 2021

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“…In addition, some VOs are not used in the food industry and present elevated unsaturation degree (iodine value, IV) or are a waste from some industrial process; such as the grape seed oil (GSO) that presents both properties. 20 In a previous paper, 21 it was reported the evaluation of maleic anhydride (MA, Figure 1b) incorporation into soybean VO using microwave irradiation; it was verified that the most elevated incorporation into soybean VO (1.45 × 10 -3 mol of MA per gram of soybean oil) occurred at 235 °C for 15 min. Thus, the reaction was extended to GSO, using same conditions, then, observing a similar amount of MA (1.79 × 10 -3 mol of MA per gram of GSO).…”

Section: Introductionmentioning

confidence: 86%

“…Thus, the reaction was extended to GSO, using same conditions, then, observing a similar amount of MA (1.79 × 10 -3 mol of MA per gram of GSO). 20 Although both VO presented similar IV and it was used the same anhydride (MA), properties such as viscosity were significant different.…”

Section: Introductionmentioning

confidence: 99%

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Effect of Isomerization and Copolymerization of Itaconic Anhydride During the Synthesis of Renewable Monomers Using Vegetable Oils

Gaglieri¹,

Alarcon²,

Moura³

et al. 2023

J. Braz. Chem. Soc.

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Vegetable oils are alternatives to producing renewable monomers since they are biomass. It is possible to react them with anhydrides by heating to provide monomers with high reactivity. However, after the reaction of grape seed oil with itaconic anhydride, it was observed the occurrence of parallel reactions that had not been observed when the same oil was reacted with maleic anhydride. Some articles in the literature have reported that temperature and bases can isomerize itaconic anhydride into citraconic anhydride, which is more stable at room temperature. However, they have not focused on completely understanding how this phenomenon occurred nor studied it in processes that involve microwave irradiation. Therefore, this paper presents a complete characterization and investigation about the thermal behavior of itaconic anhydride and how it can affect the monomer synthesis performed under heating.

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“…In the present paper, grapeseed oil (GSO) extracted from grape seeds, a by‐product from the wine and grape juice industries, is used. In a previous paper, two independent modification reactions of GSO were demonstrated to provide two monomers: epoxidized grape seed oil (EGSO, from the epoxidation reaction) and malenized grape seed oil (MGSO, from the maleinization reaction) 14 . Both reactions, follow the green chemistry and green engineering principles 15,16 .…”

Section: Introductionmentioning

confidence: 99%

Development of renewable thermosetting polymers based on grape seed oil derivatives

Gaglieri

Alarcon

Magri

et al. 2022

J of Applied Polymer Sci

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The demand for polymeric materials increases year by year, and most of them are derived from nonrenewable sources, and their consume has been increasing year by year. Therefore, there is a demand for research on bioderived polymers that are viable to be produced on an industrial scale. Based on the lack of polymers produced exclusively using monomers derived from vegetable oils, this paper shows the syntheses of renewable thermosetting polymers derived exclusively from grape seed oil, which is a by-product from the wine and grape juice industries. After the evaluation of the effect of using or not catalyst, it was determined that increasing 1-methylimidazole amount in the monomer mixture provides the decreasing of parallel reactions. However, thermal and mechanical properties, as well as the crosslinking density of polymers do not change significantly using 1.0% or 5.0% of catalyst (the minimal amounts needed to favor the esterification). Based on the characterization, the final polymers are not favorable in applications that require high mechanical impacts. However, they would be excellent as coatings due to their elevated crosslinking density, hydrophobic properties and homogenous surface. In addition, based on the properties observed under UV-light, they can also be used as luminescent materials.

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Green and Efficient Modification of Grape Seed Oil to Synthesize Renewable Monomers

Cited by 9 publications

References 0 publications

A new acrylated monomer from macaw vegetable oil that polymerizes without external photoinitiators

A new acrylated monomer from macaw vegetable oil that polymerizes without external photoinitiators

Effect of Isomerization and Copolymerization of Itaconic Anhydride During the Synthesis of Renewable Monomers Using Vegetable Oils

Development of renewable thermosetting polymers based on grape seed oil derivatives

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