Influence of monomeric and polymeric structure on the physical properties of thermoplastic polyesters derived from hydroxy fatty acids

Jose, Jesmy; Pourfallah, Ghazaleh; Leão, Alcides Lopes; Narine, Suresh S.

doi:10.1002/pi.4714

Cited by 9 publications

(10 citation statements)

References 42 publications

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“…Preliminary tensile tests revealed fiber tensile strengths up to 0.74 GPa depending on the crystal orientation and thus already compare to common polyethylene fibers, which typically exhibit tensile strength between 1.0 and 3.0 GPa . Narine and co-workers recently reported tensile properties of PE-9, PE-13, and PE-18 over a range of molecular weights, generated from the AB polycondensation of the corresponding ω-hydroxy esters, as well as related molecular weights, tensile strength, and crystallinity to each other …”

Section: Long-chain Aliphatic Polymersmentioning

confidence: 99%

“…281 Narine and co-workers recently reported tensile properties of PE-9, PE-13, and PE-18 over a range of molecular weights, generated from the AB polycondensation of the corresponding ω-hydroxy esters, as well as related molecular weights, tensile strength, and crystallinity to each other. 260 Concerning the mechanical properties of linear long-chain A 2 + B 2 type polyesters, Cho and Lee investigated PE-30.30. 167 However, an elongation of break of only 5% was found, indicating that the molecular weight of the material was likely insufficient.…”

Section: Typical Properties Of Long-chain Aliphatic Polyestersmentioning

confidence: 99%

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Long-Chain Aliphatic Polymers To Bridge the Gap between Semicrystalline Polyolefins and Traditional Polycondensates

2016

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Other than their established short-chain congeners, polycondensates based on long-chain difunctional monomers are often dominated by the long methylene sequences of the repeat units in their solid-state structures and properties. This places them between traditional polycondensates and polyethylenes. The availability of long-chain monomers as a key prerequisite has benefited much from advances in the catalytic conversion of plant oils, via biotechnological and purely chemical approaches, likewise. This has promoted studies of, among others, applications-relevant properties. A comprehensive account is given of long-chain monomer syntheses and the preparation and physical properties, morphologies, mechanical behavior, and degradability of long-chain polyester, polyamides, polyurethanes, polyureas, polyacetals, and polycarbonates.

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Section: Long-chain Aliphatic Polymersmentioning

confidence: 99%

Section: Typical Properties Of Long-chain Aliphatic Polyestersmentioning

confidence: 99%

Long-Chain Aliphatic Polymers To Bridge the Gap between Semicrystalline Polyolefins and Traditional Polycondensates

2016

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“…[2][3][4][5][6] Unsaturated fatty compounds are particularly interesting since they can be cleaved to shorter fragments that could be used in the preparation of bio-based surfactants [7][8][9][10] and polymers. 11,12 Besides the specific thermal cracking of ricinoleic derivatives [13][14][15] and the crossmetathesis with ethylene derivatives, [16][17][18][19] most of the reported cleavage methods rely on the use of oxidants (oxidative cleavage). Therefore, they involve the formation of oxidized intermediates that are produced in-situ or prepared on purposes.…”

Section: Introductionmentioning

confidence: 99%

“…In contrast, with the development of green and sustainable chemistry, the use of renewable resources is now often requiring the development of cleavage methods to produce chemicals with higher added-value . Among the primary components of biomass, vegetable oils and fatty acid derivatives have attracted a lot of attention due to their wide availability, low cost and low toxicity. − Unsaturated fatty compounds are particularly interesting since they can be cleaved to shorter fragments that could be used in the preparation of biobased surfactants − and polymers. , Besides the specific thermal cracking of ricinoleic derivatives − and the cross-metathesis with ethylene derivatives, − most of the reported cleavage methods rely on the use of oxidants (oxidative cleavage). Therefore, they involve the formation of oxidized intermediates that are produced in situ or prepared on purposes.…”

Section: Introductionmentioning

confidence: 99%

Organocatalytic Cleavage of Fatty 1,2-Diketones to Esters

Chavallard

Miguel

et al. 2019

ACS Sustainable Chem. Eng.

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The cleavage of a fatty 1,2-diketone derived from methyl oleate into the corresponding esters, i.e., methyl nonanoate and dimethyl azelate was studied by organocatalysis using oxygen as a clean oxidant. Only carbene generated from thiazolium salts and K 2 CO 3 could efficiently catalyze this transformation. It was found that, under the optimized conditions, the oxidative cleavage leads to the formation of a 1:1 mixture of esters and potassium carboxylates.An acidic treatment of the mixture, followed by esterification with methanol, led to the desired 2 esters with 75 and 77% yield. This protocol was extended to a range of symmetrical and unsymmetrical fatty 1,2-diketones and the corresponding esters were isolated with 61-84% yield.

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“…Vegetable oils are a high‐class renewable source for synthesis of various polymers, including polyesters . Among them, the materials resulted by polycondensation of hydroxy‐fatty acids proved to be sustainable replacements for fossil‐based polymers and were suitable for specialty and commodity applications . Notwithstanding of these benefits, improvement of catalysts and process conditions is still needed, as suggested by several reports …”

Section: Introductionmentioning

confidence: 99%

Biocatalytic Route for the Synthesis of Oligoesters of Hydroxy-Fatty acids and ϵ-Caprolactone

et al. 2018

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Developments of past years placed the bio-based polyesters as competitive substitutes for fossil-based polymers. Moreover, enzymatic polymerization using lipase catalysts has become an important green alternative to chemical polymerization for the synthesis of polyesters with biomedical applications, as several drawbacks related to the presence of traces of metal catalysts, toxicity and higher temperatures could be avoided. Copolymerization of ϵ-caprolactone (CL) with four hydroxy-fatty acids (HFA) from renewable sources, 10-hydroxystearic acid, 12-hydroxystearic acid, ricinoleic acid, and 16-hydroxyhexadecanoic acid, was carried out using commercially available immobilized lipases from Candida antarctica B, Thermomyces lanuginosus, and Pseudomonas stutzeri, as well as a native lipase. MALDI-TOF-MS and 2D-NMR analysis confirmed the formation of linear/branched and cyclic oligomers with average molecular weight around 1200 and polymerization degree up to 15. The appropriate selection of the biocatalyst and reaction temperature allowed the tailoring of the non-cyclic/cyclic copolymer ratio and increase of the total copolymer content in the reaction product above 80%. The catalytic efficiency of the best performing biocatalyst (Lipozyme TL) is evaluated during four reaction cycles, showing excellent operational stability. The thermal stability of the reaction products is assessed based on TG and DSC analysis. This new synthetic route for biobased oligomers with novel functionalities and properties could have promising biomedical applications.

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Influence of monomeric and polymeric structure on the physical properties of thermoplastic polyesters derived from hydroxy fatty acids

Abstract: Novel biodegradable thermoplastic poly(ω‐hydroxyfatty acid) polyesters that are functional equivalents of fossil‐fuel based polyethylene are synthesised from bio based vegetable oil feedstock.

Cited by 9 publications

References 42 publications

Long-Chain Aliphatic Polymers To Bridge the Gap between Semicrystalline Polyolefins and Traditional Polycondensates

Long-Chain Aliphatic Polymers To Bridge the Gap between Semicrystalline Polyolefins and Traditional Polycondensates

Organocatalytic Cleavage of Fatty 1,2-Diketones to Esters

Biocatalytic Route for the Synthesis of Oligoesters of Hydroxy-Fatty acids and ϵ-Caprolactone

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