Polyamides from unsaturated acids. I. Polyfumaramides from unsubstituted aliphatic diamines

Mortillaro, Luigi; Russo, Mario Vincenzo; Credali, Lino; Guidotti, Vincenzo

doi:10.1002/macp.1969.021260126

Cited by 18 publications

(5 citation statements)

References 4 publications

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“…The absence of the absorption band in the 980–960 cm −1 region corresponding to the trans configuration also suggests that ROPA retained the cis geometry of the isomaleimide monomer, as was also mentioned in the literature 13, 14…”

Section: Methodssupporting

confidence: 67%

Polymaleamide–polymaleimide networks

Ivanov¹,

Găină²,

Grigoraş³

2003

J of Applied Polymer Sci

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Polymaleamide-polymaleimide networks were obtained as films by the thermal treatment of mixtures with different ratios of an aliphatic-aromatic polymaleamide (PMA) and 4,4Ј-bis(maleimidodiphenylmethane) (BMI), in N-methyl-2-pyrolidinone (NMP) as a solvent. The polymaleamides were synthesized by ring-opening polyaddition of 1,6-hexamethylene-bisisomaleimide with 4,4Ј-diaminodiphenylmethane in NMP at room temperature. The networks are infusible and insoluble in organic solvents; therefore, they were studied by solid-state techniques such as IR, DSC, thermooptical analysis (TOA), TG/DTG analysis, and TEM. Thermal treatment of pure PMA and BMI occurs with the formation of crosslinked structures as proved by IR spectra. DSC and TOA curves show the appearance of chemical interactions between PMA and BMI in cured films and the formation of ordered morphologies, especially when BMI is the major component. TG/DTG and TEM results supported these observations. The PMA-polymaleimide network films present electrical insulator properties superior to individual polyamides or polyimides.

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Section: Methodssupporting

confidence: 67%

Polymaleamide–polymaleimide networks

Ivanov¹,

Găină²,

Grigoraş³

2003

J of Applied Polymer Sci

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“…Poly (Ira-nylylenerrLesu~onurnide) (MF-X D) 1 3 2 0 (250 ml) containing n-xylylcnediaminc (5.82 g) and KOII (4.96 g) was poured into a 1-1. three-nrcked flask cooled in a water bath. at 50°C.…”

Section: Polyhexurnettiylcnenlcsaconclrrli~e (Mf-hji)mentioning

confidence: 99%

Polyamides from unsaturated acids IV. Polyfumaramides from methyl‐substituted fumaric acids

1971

Self Cite

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S UMlM A R Y :Unsaturated polyamides from methyl-fumaric (2-methyl-fumaric and 2.3-dimethylfumaric) acid dichlorides and diamines, i.e. 1.6-hexamethylenediamine, 1.10-decamethylenediamine, rn-xylylenediamine, piperazine and trans-2.5-dimethylpiperazine were synthesized by low-temperature polycondensation.The polymer structures and properties were investigated by IR, X-ray, NMR, DSC, and TGA analyses.All polyamides were found t o be soluble in several volatile organic solvents : furthermore unlike polyamides derived from unsubstituted fumaric acidpolyamides from substituted fumaric acid derived from primary diamines showed melting or softening points. ZUSAMMENFASSUNG: Ungesattigte Polyamide aus 2-Methyl-und 2.3-Dimethylfumarsaure-dichloriden und Diaminen, z.B. Hexamethylendiamin, 1 .LO-Decamethylendiamin, rn-Xylylendiamin, Piperazin nnd truns-2.5-Dimethylpiperazin, wurden durch Tieftemperatur-Polykondensation synthetisiert. Die Struktur und die Eigenschaften der Polymeren wurden mittels IR-, Kontgenstrahlen, NMR-, DSC-und TGA-Analyse untersucht.Alle Polyamide sind in verschiedenen fliichtigen Losungsmitteln Ioslich. AuBerdem zeigen alle Polyamide aus substituierten Fumarsluren und prirnaren Diaminen, im Gegensatz zu denen a m unsubstituierter Fumarsaure, Schmelz-nnd Erweichungspunkte.

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“…Unsaturated polymers (UPs) are of special interest because of their possible postsynthetic modifications, , cross-linking via further radical polymerization, vulcanization, and applications thereof in 3D printed scaffolds, , bone-tissue engineering, drug carriers, bone cement, etc. Several renewable precursors such as maleic acid, muconic acid, and fumaric acid are used for the synthesis of UPs. − However, the conventional solution-phase polycondensation approach requires the byproducts generated in the reaction to be removed from the reaction mixture to enhance the polymer yield . Also, solution-state synthesis requires other reagents, activators, catalysts, and large volume of solvents for reaction and purification, which are against the concepts of green protocols and sustainability.…”

Section: Introductionmentioning

confidence: 99%

Solvent-Free and Catalyst-Free Synthesis of Cross-Linkable Polyfumaramides via Topochemical Azide-Alkyne Cycloaddition Polymerization

Pathan

Sureshan

2021

ACS Sustainable Chem. Eng.

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Unsaturated polymers are important materials having a lot of applications. Among polymers, polyamides possess a prime position due to their thermal and chemical stability. Herein, we report a simple, greener, catalyst-free, and solid-state synthesis of two unsaturated polyamides via a topochemical azidealkyne cycloaddition reaction. Two designed fumaramide monomers M1 and M2, functionalized with complementary azide and alkyne reactive motifs at the termini, reacted upon heating their crystalline powders and resulted in the formation of triazolyl-linked unsaturated polyfumaramides P1 and P2, respectively. We have characterized the reaction using various time-dependent techniques such as NMR, FTIR, PXRD, and DSC measurements. Interestingly, the monomer M1 resulted in 1,5-disubstituted triazole-linked unsaturated polyfumaramide (P1), whereas the monomer M2 polymerized into a polyfumaramide having both 1,4-disubstituted and 1,5-disubstituted triazole linkages (P2). Also, the trans-olefinic bond of both the fumaramide monomers was unaffected in the polymerization process and hence yielded unsaturated polymers having trans-olefin units in the repeating unit. Demonstrating the scope of postsynthetic modification, we have shown that unsaturation can be exploited for cross-linking via a light-induced [2 + 2] cycloaddition reaction. This first report on the solid-state synthesis of unsaturated polyfumaramides will be of great interest.

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Polyamides from unsaturated acids. I. Polyfumaramides from unsubstituted aliphatic diamines

Cited by 18 publications

References 4 publications

Polymaleamide–polymaleimide networks

Polymaleamide–polymaleimide networks

Polyamides from unsaturated acids IV. Polyfumaramides from methyl‐substituted fumaric acids

Solvent-Free and Catalyst-Free Synthesis of Cross-Linkable Polyfumaramides via Topochemical Azide-Alkyne Cycloaddition Polymerization

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