Emulsion copolymerization of vinyl monomers from soybean and olive oil: Effect of counterpart aqueous solubility

Kingsley, Kyle; Shevchuk, Oleh; Kirianchuk, Vasylyna; Kohut, Ananiy; Voronov, Stanislav; Voronov, Аndriy

doi:10.1016/j.eurpolymj.2019.07.008

Cited by 6 publications

(4 citation statements)

References 33 publications

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“…Because of the highly hydrophobic nature of HOSBM, its incorporation at high levels (above 35 wt % in the monomer feed) into biobased latexes remains a challenge. , Finite levels of aqueous solubility are required for HOSBM to be diffused from the emulsified monomer droplets through the aqueous phase into growing polymer particles during emulsion polymerization. This transport and thus HOSBM incorporation into the resulting latexes are limited by this monomer very low solubility in water.…”

Section: Resultsmentioning

confidence: 99%

Evaluation of 3-Allyl-5-vinylveratrole in Latex Copolymerization with an Acrylic Monomer from High Oleic Soybean Oil

Polunin

Burns

Serum

et al. 2021

ACS Sustainable Chem. Eng.

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Renewable 3-allyl-5-vinylveratrole (AVV) has been evaluated and classified as a biobased cross-linkable vinyl monomer in free-radical chain polymerization. AVV can be readily synthesized in four steps from vanillin, a compound available from lignin. Retained during macromolecular backbone formation, allylic unsaturation can be utilized in post-polymerization crosslinking and contribute to polymer network formation. The glasstransition temperature of the homopolymer from AVV (T g = 77 °C) indicates that incorporating its fragments into copolymers might considerably change the intermolecular interactions and physicochemical properties of the resulting materials. Reactivity ratios (r 1 , r 2 ) obtained in AVV copolymerization with styrene and calculated Q − e parameters of AVV confirm that this monomer copolymerization is described with the classical Mayo−Lewis equation. In this work, latexes from AVV and a renewable acrylic monomer from high oleic soybean oil were synthesized using the miniemulsion process. When the resulting biobased latex films are oxidatively cured, thermomechanical properties of the latex network are determined by the cross-link density, controlled by the ratio of "rigid" and "soft" fragments of AVV and the high oleic soybean oil-based monomer, respectively. Depending on the monomer ratio in the feed, polymeric materials with essentially different viscoelastic behaviors were obtained. Being a structural analogue to styrene, 3-allyl-5-vinylveratrole may function as its renewable replacement in free-radical polymerization, particularly in sustainable latexes. Assuming a variety of plant/vegetable oil-based acrylic monomers available, combining such monomers with AVV can become a promising platform for controlling properties of biobased latex polymer networks and their performance.

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Section: Resultsmentioning

confidence: 99%

Evaluation of 3-Allyl-5-vinylveratrole in Latex Copolymerization with an Acrylic Monomer from High Oleic Soybean Oil

Polunin

Burns

Serum

et al. 2021

ACS Sustainable Chem. Eng.

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“…For the emulsion copolymerization of methyl methacrylate with OVM and SBM, the reaction orders with respect to emulsifier and initiator are 0.33–0.67 and 0.56–0.69, respectively. It was shown that upon adding the highly hydrophobic POBMs into the monomer mixture, the latex polymer particles originating from micellar nucleation essentially increases [ 15 ].…”

Section: Features Of Homo- and Copolymerization Of Plant Oil-basedmentioning

confidence: 99%

“…The average molecular weight of the synthesized polymers varies in the range of 30,000–391,500. It was found that the molecular weight of the latex copolymers decreases with increasing unsaturation degree of the POBMs and their content in the reaction mixture, which is explained by degradative chain transfer to unsaturated fatty acid chains [ 15 , 33 ].…”

Section: Features Of Homo- and Copolymerization Of Plant Oil-basedmentioning

confidence: 99%

“…It should be noted that methods for the synthesis of vinyl monomers based on soybean, olive, and linseed oils through plant oil direct transesterification with N -(hydroxyethyl)acrylamide [ 10 , 12 , 13 ] has been recently developed along with methods of their copolymerization [ 14 ]. The ability of these plant oil-based monomers (POBMs) to undergo free radical (co)polymerization reactions has been confirmed and demonstrated [ 12 , 14 , 15 ]. The conversion, polymerization rate, and molecular weight of the polymers have been shown to depend on unsaturation of the plant oil chosen for POBMs synthesis [ 12 , 14 ].…”

Section: Introductionmentioning

confidence: 99%

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Non-Conventional Features of Plant Oil-Based Acrylic Monomers in Emulsion Polymerization

et al. 2020

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In recent years, polymer chemistry has experienced an intensive development of a new field regarding the synthesis of aliphatic and aromatic biobased monomers obtained from renewable plant sources. A one-step process for the synthesis of new vinyl monomers by the reaction of direct transesterification of plant oil triglycerides with N-(hydroxyethyl)acrylamide has been recently invented to yield plant oil-based monomers (POBMs). The features of the POBM chemical structure, containing both a polar (hydrophilic) fragment capable of electrostatic interactions, and hydrophobic acyl fatty acid moieties (C15-C17) capable of van der Waals interactions, ensures the participation of the POBMs fragments of polymers in intermolecular interactions before and during polymerization. The use of the POBMs with different unsaturations in copolymerization reactions with conventional vinyl monomers allows for obtaining copolymers with enhanced hydrophobicity, provides a mechanism of internal plasticization and control of crosslinking degree. Synthesized latexes and latex polymers are promising candidates for the formation of hydrophobic polymer coatings with controlled physical and mechanical properties through the targeted control of the content of different POBM units with different degrees of unsaturation in the latex polymers.

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Chemical Routes for the Transformation of Bio‐monomers into Polymers

Gomes,

Bzainia,

Almeida

et al. 2024

Plant Biomass Derived Materials

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Emulsion copolymerization of vinyl monomers from soybean and olive oil: Effect of counterpart aqueous solubility

Cited by 6 publications

References 33 publications

Evaluation of 3-Allyl-5-vinylveratrole in Latex Copolymerization with an Acrylic Monomer from High Oleic Soybean Oil

Evaluation of 3-Allyl-5-vinylveratrole in Latex Copolymerization with an Acrylic Monomer from High Oleic Soybean Oil

Non-Conventional Features of Plant Oil-Based Acrylic Monomers in Emulsion Polymerization

Chemical Routes for the Transformation of Bio‐monomers into Polymers

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