Dual role of methyl-β-cyclodextrin in the emulsion polymerization of highly hydrophobic plant oil-based monomers with various unsaturations

Kohut, Ananiy; Demchuk, Zoriana; Kingsley, Kyle; Voronov, Stanislav; Voronov, Аndriy

doi:10.1016/j.eurpolymj.2018.09.010

Cited by 15 publications

(13 citation statements)

References 38 publications

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“… General formula of the plant oil-based monomers. Reprinted from [ 32 ]. Copyright (2018), with permission from Elsevier.…”

Section: Figurementioning

confidence: 99%

“… PXRD spectra of POBMs, methyl-β-cyclodextrin, their physical mixture, and inclusion complexes ( A ) – H-SBM, ( B ) – HO-SBM. Reprinted from [ 32 ]. Copyright (2018), with permission from Elsevier.…”

Section: Figurementioning

confidence: 99%

“… DSC thermograms of hydrogenated soybean monomer, methyl-β-cyclodextrin, their physical mixture, and inclusion complex. Reprinted from [ 32 ]. Copyright (2018), with permission from Elsevier.…”

Section: Figurementioning

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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“… General formula of the plant oil-based monomers. Reprinted from [ 32 ]. Copyright (2018), with permission from Elsevier.…”

Section: Figurementioning

confidence: 99%

Section: Figurementioning

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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“…Amidst the properties of the binder, resistance to water is of particular relevance due to its pervasiveness in most applications, both in liquid and vapor form. Generally speaking, the water resistance of an emulsion polymer has been inversely related to the presence of hydrophilic components in the polymer matrix, and directly associated to the hydrophobic nature of the polymers produced . Among the hydrophilic species present in emulsion polymers, emulsifiers commonly make up the largest fraction.…”

Section: Introductionmentioning

confidence: 99%

“…However, due to the extremely low water solubility of this kind of monomers (at least three orders of magnitude lower that styrene solubility in water), which has led to call them very insoluble monomers, these studies have been confined to high‐shear miniemulsion polymerization or working in high‐pressure systems . Other alternatives rely on using significant amounts of hydrophilic species to improve aqueous phase transport of the very insoluble monomers such as cyclodextrins, or using aqueous blends of organic solvents as the continuous phase . However, these alternatives introduce their own sets of problems, such as the hydrophilic character of the cyclodextrins added that would remain on the final latex, or the additional separation stages necessary to eliminate the organic solvents used, that are considered volatile organic compounds (VOC) and should therefore be avoided.…”

Section: Introductionmentioning

confidence: 99%

Incorporation of Very Insoluble Monomers in Waterborne Coatings

Boscán

Meeuwisse

Mestach

et al. 2019

Macro Materials & Eng

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The benefits of polymerizing very insoluble monomers in aqueous media, avoiding the use of energy‐intensive procedures, by implementing two novel synthesis techniques based on the emulsifier combination in emulsion polymerization and on miniemulsification by phase inversion temperature are investigated. The performance of standalone polymers consisting of monomers, namely lauryl methacrylate, isobornyl acrylate, and 1H,1H,2H,2H‐perfluorodecyl acrylate, and of formulated binders with these monomers incorporated either through blending or in situ polymerization, is evaluated with special emphasis on their water‐barrier properties (e.g., uptake, whitening, immersion, and vapor resistance) and on their chemical resistance. The performance of the standalone polymers is found to be similar to that of polymers prepared by high‐shear miniemulsion polymerization, while the performance of the formulated binders is generally superior to a commercial coating formulation based on a binder recommended for water resistance.

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Derivatives of linseed oil and camelina oil as monomers for emulsion polymerization

Kolář,

Honzíček,

Podzimek

et al. 2023

J Mater Sci

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Acrylated methyl esters of higher fatty acids derived from camelina oil and linseed oil were synthesized through transesterification, epoxidation, and subsequent acrylation. Methyl methacrylate and butyl acrylate were copolymerized with various amounts of bio-based derivatives (5 – 30 wt% in monomer mixture) to obtain polymeric latexes for coating applications. Successful emulsion polymerizations with up to 25 wt% of the bio-based derivatives were performed with low coagulum (below 2%) and high monomer conversion (around 95%). The incorporation of bio-based derivatives into polymeric latexes was confirmed with infrared spectroscopy. Asymmetric flow field flow fractionation coupled with a multi-angle light scattering was used to analyze the synthesized copolymers in terms of their molar mass distribution. The results revealed that copolymerizing the bio-based derivatives resulted in ultra-high molar mass nanogel fractions formed because of multi-acrylated ingredients derived from polyunsaturated fatty acids. The phenomenon of nanogel formation became more pronounced for the linseed oil-based derivative. Evaluated coating properties showed that latexes comprising the bio-based derivatives provided increased water repellence (about 10° higher water contact angles were achieved for all bio-based coating compositions in contrast to a reference latex). Moreover, latexes comprising chemically modified oils in the content of 25 and 30 wt% provided water whitening-resistant coatings, making the bio-based derivatives promising candidates for replacing petroleum-based monomers in the production of sustainable latex coatings. Graphical abstract

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Dual role of methyl-β-cyclodextrin in the emulsion polymerization of highly hydrophobic plant oil-based monomers with various unsaturations

Cited by 15 publications

References 38 publications

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

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

Incorporation of Very Insoluble Monomers in Waterborne Coatings

Derivatives of linseed oil and camelina oil as monomers for emulsion polymerization

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