Polymerization of 4,6-diaminoisophthalic acid-type monomers bearing anthranilic acid ester and isatoic anhydride moieties

Yokoyama, Akihiro; Karasawa, Makoto; Kiyota, Ryohei; Taniguchi, Masahisa; Hirano, Yoshitaka; Ohta, Yoshihiro; Yokozawa, Tsutomu

doi:10.1038/pj.2014.105

Cited by 2 publications

(2 citation statements)

References 12 publications

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“…37,38 Furthermore, ladder polymer synthesis was attempted by means of polymerization of 4, bearing both o-aminobenzoic acid ester and isatonic anhydride moieties, with LiHMDS, but a linear polymer was obtained, as well as the cyclized products (Scheme 5). 39…”

Section: Monomers Based On the Resonance Effectmentioning

confidence: 68%

Transformation of Step-Growth Polymerization into Living Chain-Growth Polymerization

2015

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Section: Monomers Based On the Resonance Effectmentioning

confidence: 68%

Transformation of Step-Growth Polymerization into Living Chain-Growth Polymerization

2015

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“…In the presence of LiHMDS, the polymerization of 4 proceeded to yield polyamides with moderate molecular weight ( M n = 3350, M w = 6760). However, the matrix‐assisted laser desorption/ionization time‐of‐flight (MALDI‐TOF) mass spectrum suggested that the polymer was composed primarily of linear and cyclized compounds and did not exhibit a ladder structure . Because the positions para to the electron‐donating nitrogen atoms of 4 are substituted by electron‐withdrawing carbonyl groups, the nucleophilicity of the amino nitrogens and the electrophilicity of the carbonyl carbons are both weakened owing to the resonance effect shown in Scheme , which might impede the polymerization.…”

Section: Introductionmentioning

confidence: 99%

Polymerization of 2,5‐diaminoterephthalic acid‐type monomers for the synthesis of polyamides containing ladder unit

Yokoyama

Kuramochi

Kiyota

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

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To synthesize ladder‐type polyamides by construction of two amide bonds successively, 2,5‐diaminoterephthalic acid derivatives bearing anthranilic acid ester and isatoic anhydride moieties were synthesized and their polymerization was investigated. Polymerization of the methyl ester monomer proceeded in the presence of lithium hexamethyldisilazide (LiHMDS) as a base in tetrahydrofuran (THF). However, mass spectroscopic analysis of the product suggested that not only the bis(trimethylsilyl)amide anion of LiHMDS but also the methoxide anion eliminated at the second amide‐linkage formation reaction decomposed the isatoic anhydride unit of the growing oligomer by nucleophilic attack to disturb the polymerization. To reduce the nucleophilicity of the eliminated anion, methyl ester of the monomer was changed to phenyl ester and its polymerization was studied. The reaction conditions were optimized, and the best result was obtained when the polymerization was conducted in the presence of 1.0 equivalent of LiHMDS without additives in THF at 50 °C. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 2365–2372

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Polymerization of 4,6-diaminoisophthalic acid-type monomers bearing anthranilic acid ester and isatoic anhydride moieties

Cited by 2 publications

References 12 publications

Transformation of Step-Growth Polymerization into Living Chain-Growth Polymerization

Transformation of Step-Growth Polymerization into Living Chain-Growth Polymerization

Polymerization of 2,5‐diaminoterephthalic acid‐type monomers for the synthesis of polyamides containing ladder unit

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