Syntheses of rigid-rod but degradable biopolyamides from itaconic acid with aromatic diamines

Ali, Mohamed E.A.; Tateyama, Seiji; Kaneko, Tatsuo

doi:10.1016/j.polymdegradstab.2014.05.031

Cited by 26 publications

(41 citation statements)

References 27 publications

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“…IA has also been reported as a potential raw material for synthesis various resin such as epoxy,[ 29 ] polyesteramine,[ 30 ] polyester,[ 27–31 ] polyamide. [ 32 ] A variety of biorenewable raw materials (such as vegetable oils, polysaccharides, natural rubbers, and their derivatives) is used for producing UV-curable coatings. Therefore, the combination of renewable resource and UV-curing method will provide us a ‘green+green’ strategy to prepare the thermosetting resins derived from biomass, which should have a bright future.…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of bio-based UV curable PU acrylate resin from itaconic acid for coating applications

Patil

Phalak

Mhaske

2016

Designed Monomers and Polymers

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UV curable PUA resin was successfully synthesized from polyol based on sustainable resource originated from itaconic acid (IA), isophorone diisocyanate (IPDI) and 2-hydroxyethyl methacrylate (HEMA). A polyol was synthesized by condensation reaction of IA with 16-hexanediol in the presence of p-Toluenesulfonic acid (pTSA). The synthesized PUA resin was characterized for its structural elucidation by using Fourier Transform Infrared Spectrophotometer (FTIR), 1H and 13C NMR spectroscopy. The synthesized UV curable PUA resin was incorporated in varying concentrations in conventional PUA coating system. The effects of varying concentration of synthesized UV curable PUA resin on rheology, crystallinity, thermal and coating properties were evaluated. The rheological behavior of the resins were evaluated at variable stress and result showed decrease in viscosity of resin as concentration of synthesized UV curable PUA resin increases in conventional PUA resin. The cured coatings have been evaluated for glass transition temperature (T g) and thermal behavior by differential scanning calorimeter and thermogravimetric analysis respectively. The degree of crystallinity of the coatings was determined from X-ray diffraction patterns using the PFM program. It was found that increase in the mass proportion of IA based PUA in coatings, the coating becomes more rigid and crystalline. The synthesized UV curable PUA coatings showed interesting mechanical, chemical, solvent and thermal properties as compared to the conventional PUA. Further, cured coatings were also evaluated for gel content and water absorption.

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Section: Introductionmentioning

confidence: 99%

Design and synthesis of bio-based UV curable PU acrylate resin from itaconic acid for coating applications

Patil

Phalak

Mhaske

2016

Designed Monomers and Polymers

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“…There is also a protocol for biopolyamides synthesis using bio-monomer-itaconic acid, produced by the fermentation of Aspergillus terreus. Bio-derived itaconic acid was also used in polycondensation reactions with aromatic diamines by Ali et al to produce degradable biopolyamies [49][50][51]. Another recently raised building block for sustainable polymers is succinic acid derived from glucose.…”

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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“…In particular, the aza-Michael addition between the α,β-unsaturation of itaconic acid with an alkyl-amine can be used to generate renewable pyrrolidone-based dicarboxylic acid (BPDA) monomers. In turn, these BPDA monomers have successfully been used for the synthesis of polyesters [18,19], polyamides [20,21,22,23], and poly(ester-amide)s [24,25,26]. Though the presence of the cyclic pyrrolidone moieties are generally used to enhance the glass transition temperature [18], they also enhance the polymer’s affinity to water, resulting in an increased moisture uptake.…”

Section: Introductionmentioning

confidence: 99%

Improving the Hydrolysis Rate of the Renewable Poly(hexamethylene sebacate) Through Copolymerization of a Bis(pyrrolidone)-Based Dicarboxylic Acid

et al. 2019

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In this work, we report on the synthesis of a series of polyesters based on 1,6-hexanediol, sebacic acid, and N,N’-dimethylene-bis(pyrrolidone-4-carboxylic acid) (BP-C2), of which the latter is derived from renewable itaconic acid and 1,2-ethanediamine. Copolymers with a varying amount of BP-C2 as dicarboxylic acid are synthesized using a melt-polycondensation reaction with the aim of controlling the hydrolysis rate of the polymers in water or under bioactive conditions. We demonstrate that the introduction of BP-C2 in the polymer backbone does not limit the molecular weight build-up, as polymers with a weight average molecular weight close to 20 kg/mol and higher are obtained. Additionally, as the BP-C2 moiety is excluded from the crystal structure of poly(hexamethylene sebacate), the increase in BP-C2 concentration effectively results in a suppression in both melting temperature and crystallinity of the polymers. Overall, we demonstrate that the BP-C2 moiety enhances the polymer’s affinity to water, effectively improving the water uptake and rate of hydrolysis, both in demineralized water and in the presence of a protease from Bacillus licheniformis.

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Syntheses of rigid-rod but degradable biopolyamides from itaconic acid with aromatic diamines

Cited by 26 publications

References 27 publications

Design and synthesis of bio-based UV curable PU acrylate resin from itaconic acid for coating applications

Design and synthesis of bio-based UV curable PU acrylate resin from itaconic acid for coating applications

Modern biopolyamide-based materials: synthesis and modification

Improving the Hydrolysis Rate of the Renewable Poly(hexamethylene sebacate) Through Copolymerization of a Bis(pyrrolidone)-Based Dicarboxylic Acid

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