Preparation of Fully Aromatic Poly (Schiff base) and Cyclopolycondensation Reactions

Yoda, Naoya; Kurihara, Masaru; Bamba, Yasuo; Nakanishi, Ryoji

doi:10.1246/nikkashi1898.70.11_2057

Cited by 5 publications

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“…Yoda and co-workers [8] reacted 3,3'-benzidinedicarboxilic acid or benzidine with aromatic dialdehydes in dimethylformamide, pyridine or polyphosphoric acid and obtained only low molecular weight oligomers.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of aromatic polyimines by the condensation of aromatic dialdehyde and diamine

Suematsu

Nakamura

Takeda

1983

Colloid & Polymer Sci

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Abstra~: Film-forming aromatic polyimines were prepared by low temperature solution polymerization of aromatic dialdehyde and aromatic diamine using m-cresoL The polymerization proceeded rapidly to give high molecular weight polyimine solutions. Fibrous polymers were precipitated by pouring the solutions into anhydrous methanol. Lemon yellow-to-orange films were cast in situ from the reaction solutions. The polymers showed typical C=N stretching absorption near 1620 cm -1 in infrared spectra and had high glass transitions of over 200 ~ but showed low crystallinity.

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Section: Introductionmentioning

confidence: 99%

Synthesis of aromatic polyimines by the condensation of aromatic dialdehyde and diamine

Suematsu

Nakamura

Takeda

1983

Colloid & Polymer Sci

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New organic polymers, I. Synthesis and characterization of poly Schiff bases from benzidine‐3,3′‐dicarboxylic acid

Suthar

Patel

1981

Angew. Makromol. Chem.

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Thermally stable and semiconducting polymers are synthesized by condensing benzidine-3,3 '-dicarboxylic acid (BDC), with dicarbonyl compounds like glyoxal, cyclohexane-1,4-dione, 4,4'-diacetyl diphenyl ether and benzil under different experimental conditions. These poly Schiff bases are insoluble in common organic solvents. They are characterized by IR-and viscosity studies, thermal analysis, and the study of electrical properties at various temperatures. Variation of the electrical conductivity, o, with temperature was found to confirm with the empirical relation: = oo . e-E/kT ZUSAMMENFASSUNG:Thermisch bestiindige und halbleitende Polymere wurden durch Kondensation von Benzidin-3.3 'dicarbondure mit Dicarbonylverbindungen wie Glyoxal, Cyclohexan-1,4dion, 4,4 '-Diacetyldiphenylether und Benzil bei unterschiedlichen experimentellen Bedingungen hergestellt. Diese Poly-Schiff-Basen sind in herkOmmlichen organischen LOsungsmitteln unlOslich. Sie wurden mittels IR-und Viskositltsuntersuchungen, thermischer Analyse und Untersuchung der elektrischen Eigenschaften bei verschiedenen Temperaturen charakterisiert. Die Temperaturabhiingigkeit der elektrischen Leitfiihigkeit o ergab eine Bestatigung der empirischen Beziehung:

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Cyclopolycondensation. XII. Polymerization mechanism of polybenzoxazinones in polyphosphoric acid medium

Kurihara

Saitô

Nukada

et al. 1969

J. Polym. Sci. A‐1 Polym. Chem.

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The polymerization mechanism of polyphosphoric acid (PPA) solution polymerization of an aromatic diaminodicarboxylic acid with aromatic dicarboxylic acid derivatives was studied. By means of NMR methods, the initiation process for the polymerization of polybenzoxazinone in PPA medium was elucidated. The NMR spectra of a series of compounds were taken, and the salt formation of amino groups of monomer with PPA and the equilibrium between the salt and the free amino group were determined. It was established that the polymerization proceeded through the formation of phosphorylated intermediates to give the salt of amino groups of monomer with PPA. In the second step, the amine–PPA salt dissociates into the free amino group and PPA at the polymerization temperature above 140°C. Polymerization proceeds through the attack of “free” amino on phosphorylated carbonyl compounds to form polyamide acid of high molecular weight, and on subsequently being heated in PPA at higher temperatures, it undergoes an intramolecular cyclodehydration along the polymer chain to form polybenzoxazinones.

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Preparation of Fully Aromatic Poly (Schiff base) and Cyclopolycondensation Reactions

Cited by 5 publications

References 0 publications

Synthesis of aromatic polyimines by the condensation of aromatic dialdehyde and diamine

Synthesis of aromatic polyimines by the condensation of aromatic dialdehyde and diamine

New organic polymers, I. Synthesis and characterization of poly Schiff bases from benzidine‐3,3′‐dicarboxylic acid

Cyclopolycondensation. XII. Polymerization mechanism of polybenzoxazinones in polyphosphoric acid medium

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