Hydrogen bonding and crystalline structure of bio-based PA56

Yang, Tingting; Gao, Yuanbo; Wang, Xueli; Ma, Bomou; He, Yong

doi:10.1016/j.polymer.2021.124356

Cited by 28 publications

(20 citation statements)

References 36 publications

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“…Moreover, related crystalline bands from the feature of polyamide materials were weakened and even disappear with increasing temperature, which can be observed from the absorptions at 1235, 1185, 937, 721, and 692 cm À1 . [23][24][25] These results further supported the existence of ordered crystalline regions and hydrogenbonding networks in cPAs, and that a "more free" reversible networked structure made cPA materials to exhibit more flexible and adjustable mechanical properties with the evolution of temperature.…”

Section: Dynamic Mechanical Analysis Of Cpasmentioning

confidence: 55%

Synthesis and characterization of ultra‐tough crosslinked polyamide with hybrid polymer networks equipping strong hydrogen bonds

Chen

Chang

Rwei

2022

J of Applied Polymer Sci

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In this work, a novel crosslinked polyamide (cPA) system with hybrid polymer networks was developed. The hexamethylenediamine, acrylic acid (AA), and bis(6-aminohexyl) dodecanediamide (BAHD) were utilized as the main building block in crosslinked polyamide (cPA) system by Michael addition reaction and polycondensation, wherein an amide diamine monomer, BAHD, was utilized as the building provider of hydrogen-bonding networks. Simultaneously, the internal covalent bond networks were constructed by the Michael addition between AA and diamine, resulting in permanent covalent crosslinks. By adjusting the ratio of BAHD content, a series of copolyamides were successfully synthesized, and the thermal, mechanical, and viscoelastic behavior of cPAs were systematically discussed. Based on these results, the best mechanical properties in our cPAs were found in the composition of BH37, which exhibited microcrystalline behavior and outstanding tensile properties with melting temperature of 55 C, tensile strength above 45 MPa, and elongation at break above 1000%. It demonstrated that the adjusting of reversible hydrogen bonds and permanent covalent crosslinks in hybrid polymer networks could effectively endow the cPAs with excellent flexibility and strength. These studies provide useful information for designing novel cPA materials with controlled thermal and mechanical properties, which suggested the potential for use in advanced application fields.

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Section: Dynamic Mechanical Analysis Of Cpasmentioning

confidence: 55%

Synthesis and characterization of ultra‐tough crosslinked polyamide with hybrid polymer networks equipping strong hydrogen bonds

Chen

Chang

Rwei

2022

J of Applied Polymer Sci

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“…In the spectrum of PA56, the characteristic bands around 3300 and 3085 cm −1 are associated with the stretching vibration of NH of amide A and amide B, respectively. The peak around 1642 cm −1 corresponds to the stretching vibration of CO, while the peak at 1548 cm −1 is attributed to the CN stretch vibrations and NH bending 1 . Those characteristic peaks of PA56 (3300, 3085, 1642, and 1548 cm −1 ) all appear in the spectra of FRPA56s.…”

Section: Resultsmentioning

confidence: 95%

“…Recently, polymers derived from renewable resources have attracted much attention as a consequence of the elevated environmental awareness of the public. Biobased polyamide 56 (PA56) is a novel industrial biobased polyamide produced by Cathay Biotechnology Incorporation from its proprietary biobased 1,5‐pentanediamine (PDA) monomer 1 . PA56 displays excellent comprehensive performance.…”

Section: Introductionmentioning

confidence: 99%

“…Biobased polyamide 56 (PA56) is a novel industrial biobased polyamide produced by Cathay Biotechnology Incorporation from its proprietary biobased 1,5-pentanediamine (PDA) monomer. 1 PA56 displays excellent comprehensive performance. Furthermore, PA56 displays high moisture absorption, easy dyeing, and good melt-flowability due to its odd-numbered-carbon molecular structure and is widely used in textiles and engineering materials.…”

Section: Introductionmentioning

confidence: 99%

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Flame‐retardant polyamide 56 with high fire safety and good thermal performance

Yang

Gao

Liu

et al. 2022

Polymers for Advanced Techs

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As a recently developed biobased polyamide, polyamide 56 (PA56) has great potential in the field of fibers and textiles due to its high strength, high moisture absorption, and easy dyeing. However, the application of PA56 is restricted due to its flammability. Flame‐retardant PA56 copolymers (FRPA56s) have been designed and successfully synthesized by the introduction of 2‐carboxyethyl(phenyl)phosphinic acid (CEPPA) monomer. The thermal properties and thermal stability of FRPA56s have been evaluated using DSC and TGA, respectively. The flammability behavior of the resultant copolymer has been investigated using UL94 vertical burning and cone calorimetry tests. The crystallization temperature (Tc), melting temperature (Tm), and crystallinity (Xc) of FRPA56s are reduced and the degradation pathway for PA56 is changed with the introduction of CEPPA. In addition, FRPA56 containing 7.8 mol% CEPPA may be characterized by a V‐0 rating in the UL94 vertical burning test and its total heat release is reduced 20% than that of PA56, reflecting the high flame‐retardant efficiency of CEPPA. Based on the analysis of the residual char and the gas‐phase pyrolysis products for combustion of FRPA56s, it is concluded that the flame‐retardant modes of action for this material mainly include flame inhibition, dilution effect and charring.

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“…The crystalline form of PA5T/56 was consistent with that of PA56. Melt crystallization was γ-crystal form, dilute solution crystallized into α-like crystal form. − PA5T/56 exhibited heteromorphism and had the crystal structure similar to PA56 because terephthalic acid in the 5T structure unit and adipic acid in the 56 structure unit had highly similar molecular conformation and spatial structure in the crystal structure Figure b displays the crystallization curves of PA5T/56 at different cooling rates.…”

Section: Resultsmentioning

confidence: 99%

Bio-Based Pentamethylenediamine-Derived Semiaromatic Copolyamide: Controllable Synthesis and Discoloration Mechanism

Yang

Guo

Liu

et al. 2022

Ind. Eng. Chem. Res.

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The long-ignored discoloration behavior of polyamide during polymerization has a significant impact on its properties and applications. Here, we innovatively analyzed the discoloration behavior of pentamethylenediamine-derived bio-based copolyamide (PA5T/56) and proposed a possible discoloration mechanism. Pentamethylenediamine performed cyclization reactions at high temperature to generate piperidine, which was then combined with terephthalic acid to form dipiperidine terephthalate. After being oxidized, dipiperidine terephthalate was converted to terephthalic acid bis(2-carbonyl substituted piperidine), which was believed to be responsible for the discoloration of polyamide during polymerization. Moreover, it was demonstrated that the discoloration behavior led to poor spinnability and dyeability of ultrafine polyamide fibers. This work will help to optimize the polymerization process of pentamethylenediamine-derived polyamide and expand its applications in high-performance fibers and other fields.

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Hydrogen bonding and crystalline structure of bio-based PA56

Cited by 28 publications

References 36 publications

Synthesis and characterization of ultra‐tough crosslinked polyamide with hybrid polymer networks equipping strong hydrogen bonds

Synthesis and characterization of ultra‐tough crosslinked polyamide with hybrid polymer networks equipping strong hydrogen bonds

Flame‐retardant polyamide 56 with high fire safety and good thermal performance

Bio-Based Pentamethylenediamine-Derived Semiaromatic Copolyamide: Controllable Synthesis and Discoloration Mechanism

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