The Development of Epoxidized Hemp Oil Prepolymers for the Preparation of Thermoset Networks

Omonov, Tolibjon S.; Patel, Vinay R.; Curtis, Jonathan M.

doi:10.1002/aocs.12290

Cited by 15 publications

(12 citation statements)

References 49 publications

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“…Detailed interpretations of the FTIR spectra of plant oils and oil derivatives can be found in the literature. 27,44 For LO, Figure 3 shows the C�C−H double bond stretch at 3006 cm −1 and C�C vibrations at 1655 cm −1 ; these disappear in the epoxidized oil derivatives. The transformation of double bonds into epoxy groups is confirmed by the appearance of the new band at 826 cm −1 , which corresponds to the C−O−C stretching from the oxirane vibration.…”

Section: Resultsmentioning

confidence: 99%

Biobased Thermosets from Epoxidized Linseed Oil and its Methyl Esters

Omonov

Patel

Curtis

2022

ACS Appl. Polym. Mater.

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This work describes a model biobased epoxy thermoset resin incorporating epoxidized linseed oil fatty acid methyl esters (ELOMEs) with trimellitic anhydride (TMA) as a curing agent. Unlike epoxidized linseed oil (ELO), ELOME acts as a solvent at moderate temperatures and can dissolve the curing agent. Thermosets were prepared using a range of molar ratios of ELOME, or ELOME/ELO mixtures, to TMA. It was found that the storage moduli and glass-transition temperatures of the resulting thermosets increase with the increasing concentration of the curing agent due to enhanced crosslinking. On the other hand, the dynamic mechanical analysis demonstrated that an increase in the curing agent content, especially above the stoichiometric ratios of reactive moieties, hinders the formation of the cross-linked network when an excessive amount of TMA esters of ELOME are formed. These consume a large proportion of the available epoxy moieties and consequently limit further cross-linking and polymer network growth. The glass-transition temperature (T g ) of these resins was between 80 and 86 °C, depending on the stoichiometric ratio of the reactive moieties. In thermoset systems prepared with ELOME/ ELO mixtures, an improvement in the thermomechanical properties (increase of T g up to 102 °C) was observed, which was associated with the increase in cross-linking density resulting from the branched triacylglycerol structure of epoxidized linseed oil.

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Section: Resultsmentioning

confidence: 99%

Biobased Thermosets from Epoxidized Linseed Oil and its Methyl Esters

Omonov

Patel

Curtis

2022

ACS Appl. Polym. Mater.

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“…Compared to the nontechnical challenges, the authors of this manuscript feel that the technical challenges that face the development of cannabis-based bioproducts are much more readily apparent as they incorporate many of the same issues that face other bioproducts. For example, like other plant oils, hemp seed oil has a high oxygen content which in turn makes it susceptible to oxidation. , Other technical challenges facing cannabis, which are also common to other biorefinery crops, include ensuring uniformity of feedstock and reducing overall water and energy consumption. In light of the above, the authors have identified the following specific technical opportunities:…”

Section: Challenges and Opportunities In The Development Of Hemp-base...mentioning

confidence: 99%

“…Omonov et al 33 blended epoxidized hempseed oil with one of two different curing agents (trimetallic anhydride (TMA) and citric acid (CA)) in order to prepare epoxy thermosets. Compared to the processes used by Surender et al 122 and Shuttleworth et al 123 the process used by Omonov et al 26 differed mainly in the choice of curing agents.…”

Section: Solid Materials From Hempmentioning

confidence: 99%

“…For example, like other plant oils, hemp seed oil has a high oxygen content which in turn makes it susceptible to oxidation. 123,33 Other technical challenges facing cannabis, which are also common to other biorefinery crops, include ensuring uniformity of feedstock and reducing overall water and energy consumption. In light of the above, the authors have identified the following specific technical opportunities:…”

Section: Challenges and Opportunities In The Development Of Hemp-base...mentioning

confidence: 99%

“…To date, scientists and engineers have found numerous applications for hemp stems and hemp seeds, including in pulp and paper making, ,, building materials, − textiles, − porous carbon, − composite polymers, − biofuels, − essential oils, and chemical precursors. − Given the number of products that can be produced from cannabis, plus the expected worldwide growth in the legal supply of legal cannabis, it is becoming increasingly possible to envision cannabis as a feedstock in a circular economy, whose key characteristics include the increased use of renewable resources and the valorization of process waste streams. However, the current knowledge base of cannabis-derived bioproducts is spread out over a wide range of academic disciplines that spans science, engineering, agriculture, forestry, medicine, and public policy.…”

Section: Introductionmentioning

confidence: 99%

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Cannabis as a Feedstock for the Production of Chemicals, Fuels, and Materials: A Review of Relevant Studies To Date

Gomez

Clarke

2021

Energy Fuels

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As societies place greater emphasis on sustainability, there is a move toward creating a circular economy in which renewable resources, such as agriculture and forestry residues, serve as feedstocks in the production of energy and chemicals. One emerging agricultural commodity that may potentially serve as a feedstock for numerous chemicals and materials is cannabis. For most of the last one hundred years the use of cannabis as a biomass feedstock has been all but impossible, due to its legal status. However, over the last 20 years the changing legal status of cannabis has resulted in a large number of studies which have investigated cannabis as a feedstock for diverse bioproducts, including polymers, pulp, and biofuels. Being a relatively new agricultural commodity, the literature on chemicals, fuels, and materials derived from cannabis is spread across numerous disparate disciplines, such as engineering, agriculture, chemistry, and biology. Thus, the purpose of this review is to compile and summarize the relevant studies that illustrate the use of cannabis as a feedstock in the production of chemicals, fuels, and materials as well as to highlight the challenges and possibilities for future research opportunities.

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A review of fatty epoxide ring opening reactions: Chemistry, recent advances, and applications

Moser

Cermak

Doll

et al. 2022

J Americ Oil Chem Soc

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Fatty epoxides are produced from the corresponding alkenes by oxidation in the presence of peracids or other oxidants. The classic method is the Prilezhaev epoxidation in which peracids are generated by in situ oxidation of formic or acetic acids with hydrogen peroxide. Epoxidized vegetable oils and esters are used directly as biobased plasticizers and stabilizers for poly(vinyl chloride) or as important platform chemicals for the oleochemical industry. Nucleophilic attack at the oxirane moiety affords a variety of ring opened monomeric or polymeric products, which in many cases undergo further synthetic modification to yield finished products. The most common nucleophiles include water, alcohols, carboxylic acids, acid anhydrides, and amines, although numerous others can also lead to valuable functionalized fatty derivatives. This review summarizes the chemistry of fatty epoxide ring opening reactions as well as applications of the resultant products. Literature from the last 20 years will be emphasized, although older publications of particular significance will be included. Important applications include biobased lubricants as well as polyols for subsequent production of polyurethanes. In addition, ring-opening reactions hitherto unreported on fatty oxiranes will be suggested to facilitate further advancements in the chemistry and utility of fatty epoxides. Finally, interest in fatty epoxides and their consequent products will continue to grow due to the simplicity, efficiency, and versatility of oxirane formation and ring opening as well as the continued societal transition away from petroleum to a sustainable, circular, low-carbon, and biobased economy.

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The Development of Epoxidized Hemp Oil Prepolymers for the Preparation of Thermoset Networks

Cited by 15 publications

References 49 publications

Biobased Thermosets from Epoxidized Linseed Oil and its Methyl Esters

Biobased Thermosets from Epoxidized Linseed Oil and its Methyl Esters

Cannabis as a Feedstock for the Production of Chemicals, Fuels, and Materials: A Review of Relevant Studies To Date

A review of fatty epoxide ring opening reactions: Chemistry, recent advances, and applications

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