Fatty acid derived renewable polyamides via thiol–ene additions

Türünç, Oğuz; Firdaus, Maulidan; Klein, Gregor; Meier, Michael A. R.

doi:10.1039/c2gc35982k

Cited by 86 publications

(51 citation statements)

References 28 publications

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“…Next, ester 1 was treated with 1,1′-azobis(cyclohexanecarbonitrile) (ABCN) and 2-mercaptoethylamine hydrochloride in dioxane/ethanol 70:30 (v:v) to obtain methyl 11-(2-aminoethylthio)undecanoate ( 2 ) in 89% yield. The structures of compounds 1 and 2 were in agreement with the reported literature data [14–15]. …”

Section: Resultssupporting

confidence: 89%

“…This crude product mixture was concentrated and purified by column chromatography with hexane/ethyl acetate (92:8, v/v) to obtain pure methyl 11-(2-aminoethylthio)undecanoate ( 2 ) in 89% yield (7.41 g). The purified product was characterized by 1 H and 13 C NMR, IR and ESIMS spectral studies and the structure was confirmed by comparing the data with those reported in the literature [15]. …”

Section: Methodsmentioning

confidence: 94%

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Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids

Narra¹,

Kaki²,

Misra³

et al. 2017

Beilstein J. Org. Chem.

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The synthesis of five novel methyl 10-undecenoate-based lipoconjugates of phenolic acids from undecenoic acid was carried out. Undecenoic acid was methylated to methyl 10-undecenoate which was subjected to a thiol–ene reaction with cysteamine hydrochloride. Further amidation of the amine was carried out with different phenolic acids such as caffeic, ferulic, sinapic, coumaric and cinnamic acid. All synthesized compounds were fully characterized and their structures were conﬁrmed by spectral data. The anti-oxidant activity of the synthesized lipoconjugates of phenolic acids was studied by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay and also by the inhibition of linoleic acid oxidation in micellar medium by differential scanning calorimetry (DSC). The prepared compounds were also screened for their cytotoxic activity against five cell lines. It was observed that the lipoconjugates of caffeic acid, sinapic acid, ferulic acid, and coumaric acid displayed anticancer and anti-oxidant properties. The anticancer properties of these derivatives have been assessed by their IC50 inhibitory values in the proliferation of MDA-MB231, SKOV3, MCF7, DU 145 and HepG2 cancer cell lines.

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Section: Resultssupporting

confidence: 89%

Section: Methodsmentioning

confidence: 94%

Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids

Narra¹,

Kaki²,

Misra³

et al. 2017

Beilstein J. Org. Chem.

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“…Dimer fatty acid-based polyamides are a special class of biopolymers derived from plant oils [1,18,19]. Compared to other polyamides, they feature lower water uptake and ease of processing (owing to a lower melt viscosity).…”

Section: Introductionmentioning

confidence: 99%

Surfactant-free dimer fatty acid polyamide/montmorillonite bio-nanocomposites

Macheca

Gnanasekaran²,

Focke³

2013

Colloid Polym Sci

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Polyamide bio-nanocomposites were successfully prepared using a surfactant-free approach. The clay morphology was fixed by dispersing the ammonium ion-exchanged clay in acetic acid. This was mixed wi th an aceti c aci d sol uti on of the polyamide and the composite was recovered by precipitation with water. The composites featured a mixed morphology containing some exfoliated clay sheets together with nano-sized clay tactoids.Bio-nanocomposites containing as much as 27.5 wt.% clay were obtained. At this filler level, and depending on the temperature, the modulus was up to nine times higher than that of the parent polymer. Addition of clay also increased the glass transition temperature by as much as 5°C. This indicates that the high interfacial surface area, presented by the clay platelets dispersed in the matrix, significantly impaired the polymer chain mobility.

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“…Another strategy for derivatization of unsaturated fatty acid methyl esters was direct synthesis of keto-fatty acid esters by Wacker oxidations employing oxygen as a sole re-oxidant and amine functionalization of the thus obtained keto-fatty acid esters by reductive amination [41]. In another work, unsaturated bond of fatty acid-derived methyl 10-undecenoate, methyl oleate, and methyl erucate was utilized in the thiol-ene addition reaction of cysteamine hydrochloride to obtain amine functional branched monomers [42]. Monomers were further used to obtain homo and copolymers with adjustable thermal and solubility properties.…”

Section: Synthesis Of Biopolyamides From Other Bio-based Monomersmentioning

confidence: 99%

Modern biopolyamide-based materials: synthesis and modification

2019

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The wider use of renewable feedstock in structural applications, where high mechanical performance is required, can be achieved by the application of recently developed engineering biopolymers and their further modification by micro-and nanoparticles. In this review, we present the current state of the art of biopolyamide materials for structural and functional applications. The overview includes all stages of the manufacturing-from the synthesis of building blocks, through the synthesis of polymers and its physical modification, with special emphasis on the properties of the obtained engineering biocomposites as a final product of modern polymer technology. In the first part, the synthetic routes of bio-derived counterparts of common polyamides as well as specialty polymers with functional properties arising from the complex structure of biochemicals were exemplified. The development of environmentally friendly composites and nanocomposites based on biopolyamides and natural fillers, such as plant fibers or cellulosic nanofibers, was of particular interest due to preserved sustainable character of such materials.

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Fatty acid derived renewable polyamides via thiol–ene additions

Cited by 86 publications

References 28 publications

Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids

Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids

Surfactant-free dimer fatty acid polyamide/montmorillonite bio-nanocomposites

Modern biopolyamide-based materials: synthesis and modification

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