Robust Amidation Transformation of Plant Oils into Fatty Derivatives for Sustainable Monomers and Polymers

Yuan, Liang; Wang, Zhongkai; Trenor, Nathan M.; Tang, Chuanbing

doi:10.1021/acs.macromol.5b00091

Cited by 90 publications

(61 citation statements)

References 68 publications

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“…Tang et al [ 16 ] reported on the synthesis of N -hydroxyalkylamides and methacrylate hydrophobic monomers through the interaction of plant oil triglycerides with amino alcohols ( Figure 1 ). They developed a new interesting approach that involves the use of a two-step process.…”

Section: Features Of Synthesis Of Vinyl Monomers From Plant Oilsmentioning

confidence: 99%

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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Section: Features Of Synthesis Of Vinyl Monomers From Plant Oilsmentioning

confidence: 99%

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

et al. 2020

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“…Diels−Alder reactions can also be exploited as a tool for post‐polymerization of bio‐derived polymers. Tang and co‐workers developed fatty‐acid‐derived poly(meth)acrylates by a transesterification of vegetable oil with ethanol amine . The unsaturated fatty acid pendants were modified via thiol‐ene click chemistry to introduce furan moieties, which can be used as dienes in Diels−Alder reactions (Scheme ) .…”

Section: Post‐polymerization Modification Via Ccmentioning

confidence: 99%

Post‐polymerization modification of bio‐based polymers: maximizing the high functionality of polymers derived from biomass

Farmer

Comerford

Pellis

et al. 2018

Polymer International

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The renaissance of the bio-based chemical industry over the last 20 years has seen an ever growing interest in the synthesis of new bio-based polymers. The building blocks of these new polymers, so called platform molecules, contain significantly more chemical functionality than their petrochemical counterparts (such as ethene, propene and para-xylene). As a result bio-based polymers often contain greater residual chemical functionality in their chains, with groups such as alkenes and hydroxyls commonly observed. These functional groups can act as sites for post-polymerization modification (PPM), thus further extending the range of applications for bio-based polymers by tailoring the polymers' final properties. This mini-review highlights some of the most recent and compelling examples of how to make use of bio-based polymers with residual functional groups for PPM. It also looks at how the emerging interdisciplinary field of enzymatic polymer synthesis allows for increased functionality in polymers by avoiding side-reactions as a result of milder reaction conditions, and additionally offers an alternative means of polymer surface modification.

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“…Indeed, recently, Maiti et al reported a new method of functionalization involving Steglich esterification of various FA (caprylic, capric, lauric, myristic, palmitic, stearic, and oleic acids [OLA]) to provide partially biobased methacrylate monomers in a one‐step method (Maiti et al, ; Maiti and De, ). Another synthetic route based on a two‐step method through amidation followed by (meth)acrylation has been recently reported by Yuan et al to provide monomers for radical polymerization (Yuan et al, ). Similarly, to find other bioalternatives, our previous work focused on the synthesis of an OLA‐based monomer, 2‐(methacryloyloxy)ethyl oleate (MAEO), which was successfully involved in free radical polymerization (FRP) and evaluated as VII (Lomège et al, ).…”

Section: Introductionmentioning

confidence: 99%

Epoxidized Oleic Acid‐Based Polymethacrylates as Viscosity Index Improvers

Lomège

Lapinte

Négrell

et al. 2019

J Americ Oil Chem Soc

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This study reports two routes for the synthesis of epoxidized oleic acid (OLA)‐based polymethacrylates. The first one consisted of the synthesis followed by epoxidation of the OLA‐based methacrylate, 2‐(methacryloyloxy)ethyl oleate (MAEO), prior to its radical polymerization. In the second pathway, MAEO was first homopolymerized to afford poly(2‐(methacryloyloxy)ethyl oleate) (PMAEO) and, then, the internal double bonds of the oleate were epoxidized at different yields ranging from 20% to 100%. All polymeric structures were confirmed using 1H nuclear magnetic resonance (NMR), and characterized through size‐exclusion chromatography (SEC), thermogravimetric analysis (TGA), and differential scanning calorimetry (DSC) analyses. The resulting polymers were then blended at 5 wt.% in a mineral paraffinic oil (MPO) and in a biobased organic triacylglycerol oil (OTO) to be evaluated as viscosity index improvers (VII). The partially epoxidized polymers up to 40% were soluble in MPO. According to a rheological study, the oil‐soluble epoxidized polymers resulting from the epoxidation of PMAEO exhibited a much higher influence on oil viscosities at high temperatures than at low temperatures compared to the low‐epoxidized PMAEO molecular weight obtained by the first strategy. Additionally, the viscosity indices of both lubricating oils were significantly improved with the addition of the epoxidized OLA‐based polymers resulting from the epoxidation of PMAEO, which confirmed their efficiency as VII.

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Robust Amidation Transformation of Plant Oils into Fatty Derivatives for Sustainable Monomers and Polymers

Cited by 90 publications

References 68 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

Post‐polymerization modification of bio‐based polymers: maximizing the high functionality of polymers derived from biomass

Epoxidized Oleic Acid‐Based Polymethacrylates as Viscosity Index Improvers

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