Synthesis and Characterization of Unsaturated Biobased-Polyamides from Plant Oil

Ahmadi, Reza; Ullah, Aman

doi:10.1021/acssuschemeng.0c02692

Cited by 16 publications

(9 citation statements)

References 48 publications

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“…Nomura and Awang reviewed the many contributions available based on the synthesis of 1,ω-fatty acid diesters and diols, which can be used as monomers for the synthesis of long-chain aliphatic polyesters by numerous routes [ 100 ]. A facile route for semi-aromatic polyamides from dimethyl 9-octadecenedioate and p -xylylenediamine or diethylenetriamine was reported, leading to materials with good thermal and mechanical properties [ 101 ].…”

Section: Broadening the Horizon: Bio-based Routes For Original Polymersmentioning

confidence: 99%

Monomers and Macromolecular Materials from Renewable Resources: State of the Art and Perspectives

Gandini

Lacerda

2021

Molecules

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A progressively increasing concern about the environmental impacts of the whole polymer industry has boosted the design of less aggressive technologies that allow for the maximum use of carbon atoms, and reduced dependence on the fossil platform. Progresses related to the former approach are mostly based on the concept of the circular economy, which aims at a thorough use of raw materials, from production to disposal. The latter, however, has been considered a priority nowadays, as short-term biological processes can efficiently provide a myriad of chemicals for the polymer industry. Polymers from renewable resources are widely established in research and technology facilities from all over the world, and a broader consolidation of such materials is expected in a near future. Herein, an up-to-date overview of the most recent and relevant contributions dedicated to the production of monomers and polymers from biomass is presented. We provide some basic issues related to the preparation of polymers from renewable resources to discuss ongoing strategies that can be used to achieve original polymers and systems thereof.

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Section: Broadening the Horizon: Bio-based Routes For Original Polymersmentioning

confidence: 99%

Monomers and Macromolecular Materials from Renewable Resources: State of the Art and Perspectives

Gandini

Lacerda

2021

Molecules

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“…In another publication, linear polyamide films from an unsaturated diester of canola oil, dimethyl 9-octadecenedioate, and p-xylenediamine or diethylenetriamine were synthesized and characterized. The presence of unsaturations in the polymer backbone allowed postpolymerization functionalizations to insert side chains and tune the final properties of the materials [ 92 ]. A very interesting approach for the synthesis of polycarbonates was reported by Cramail’s group, based on the controlled polymerization of a fatty acid-based cyclic carbonate-bearing an unsaturation.…”

Section: Linear Polymers Based On Fatty Acids or Their Ensuing Derivativesmentioning

confidence: 99%

The Prospering of Macromolecular Materials Based on Plant Oils within the Blooming Field of Polymers from Renewable Resources

et al. 2021

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This paper provides an overview of the recent progress in research and development dealing with polymers derived from plant oils. It highlights the widening interest in novel approaches to the synthesis, characterization, and properties of these materials from renewable resources and emphasizes their growing impact on sustainable macromolecular science and technology. The monomers used include unmodified triglycerides, their fatty acids or the corresponding esters, and chemically modified triglycerides and fatty acid esters. Comonomers include styrene, divinylbenzene, acrylics, furan derivatives, epoxides, etc. The synthetic pathways adopted for the preparation of these materials are very varied, going from traditional free radical and cationic polymerizations to polycondensation reactions, as well as metatheses and Diels–Alder syntheses. In addition to this general appraisal, the specific topic of the use of tung oil as a source of original polymers, copolymers, and (nano)composites is discussed in greater detail in terms of mechanisms, structures, properties, and possible applications.

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“…Conventional polyamide-11 derived from α-amino acid monomers can be obtained from renewable castor oils and is highly desirable for industrial applications as an environment-friendly engineering polymer. [3,4] Sugar-derived polyamides are containing a heterocyclic ring with tunable T g have been prepared using monomers such as 1,4;3,6-dianhydro-d-glucidol (isosorbide), biodegradation. Additionally, it is notable that the N-substituted pyrrolidone ring has a mixture of R/S configurations (stereo random), which affects stereoregularity for a more extended chain order in the polymer backbone.…”

Section: Introductionmentioning

confidence: 99%

“…[5][6][7][8] However, low T g values of biobased polyamides restrict their application. [3][4][5][6][7][8] On the other hand, considerable progress has been made in the syntheses of enantiomeric d-and l-poly(hexamethylene di-Omethyltartaramide)s {P6DMT(d-/l-)} a pair of stereoregular polyamides is reported. [9][10][11] The (+)-3-carene based chiral polyamides such as poly-3R-caranamide and poly-3S-caranamide have high T g (70-100 °C).…”

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confidence: 99%

High‐Performance BioNylons from Itaconic and Amino Acids with Pepsin Degradability

Ali

Kaneko

2021

Advanced Sustainable Systems

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dianhydro-d-mannitol (isomannide), and 1,4,3,6-dianhydro-l-iditol (isoidide). [5][6][7][8] However, low T g values of biobased polyamides restrict their application. [3][4][5][6][7][8] On the other hand, considerable progress has been made in the syntheses of enantiomeric d-and l-poly(hexamethylene di-Omethyltartaramide)s {P6DMT(d-/l-)} a pair of stereoregular polyamides is reported. [9][10][11] The (+)-3-carene based chiral polyamides such as poly-3R-caranamide and poly-3S-caranamide have high T g (70-100 °C). [2] Besides, terpenes-based chiral polyamide, which were derived from (R)-(+)-, (S)-(-)limonene, and (-)-β-pinene showed the T g value in the range of 40-42 °C. [2,12,13] Enhancement of interchain interaction based on chirality should be effective on increasing the softening temperature of the polymers. The polyamides have a synergistic effect on chiral interaction and hydrogen bonding between the different moieties. [11,14,15] Recently, we have reported the preparation of polyamides with heterocyclic amide ring such as pyrrolidone to increase the T g , owing to the rigidity and interchain hydrogen bonding. [16][17][18] The pyrrolidone ring was derived from itaconic acid (IA), which is a notable bio-renewable resource that can be mass-produced from Aspergillus terreus via fermentation using glucose. [17][18][19] IA reacted with amine compounds through its corresponding salt monomer to form heterocyclic pyrrolidone by aza-Michael addition of amines to IA's double bond successive ring-closing condensation with a carboxylic acid upon heating. [20,21] N-substituted amide linkage restricts water absorption, which can contribute to reducing the thermal and mechanical properties of the resulting polymer. [22] The pyrrolidone ring-based polyamides showed corrosive behavior in soil and photo-induced solubilization under UV light, which induce hydrolytic ring-opening. [21,23,24] In particular, symmetrical bis(pyrrolidone)-based dicarboxylic acids prepared from itaconic acid are polymerized and yield amorphous and degradable polymers with low T g values that are susceptible to enzymatic depolymerization. [25,26] However, conventional nonchiral polyamides such as nylon 6, nylon 66, and nylon 11 are not degradable whereas polyamides (nylon 4 and its copolymer nylon-4,4 and -5,4), which were derived from γ-aminobutyric acid (GABA) are biodegradable. [27][28][29] The polyamides from symmetrical monomers were studied, but monomers having head-tail asymmetry such as amino acids should be effective on The use of renewable feedstock for polymers has led to poor thermomechanical properties with high production costs. Herein, the production of novel chiral dicarboxylic acids derived from renewable itaconic and amino acids (d-or l-leucine) is reported. In this study, rigid chiral heterocyclic dicarboxylic acid monomers are obtained with high purity from itaconic acid-derived dimethyl itaconate as a starting material. Chirally interactive polyamides are prepared via melt polycondensation of hexamethylenediamine with heterocycl...

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Synthesis and Characterization of Unsaturated Biobased-Polyamides from Plant Oil

Cited by 16 publications

References 48 publications

Monomers and Macromolecular Materials from Renewable Resources: State of the Art and Perspectives

Monomers and Macromolecular Materials from Renewable Resources: State of the Art and Perspectives

The Prospering of Macromolecular Materials Based on Plant Oils within the Blooming Field of Polymers from Renewable Resources

High‐Performance BioNylons from Itaconic and Amino Acids with Pepsin Degradability

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