Condensation polymerization of triphenylamine with carbonyl compounds

• Published in: Macromolecular chemistry and physics Vol. 200; no. 1; pp. 65 - 70
• Main Authors: Son, Jhun-Mo, Nakao, Mayumi, Ogino, Kenji, Sato, Hisaya
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag GmbH 01.01.1999; WILEY‐VCH Verlag GmbH; Wiley
• Subjects: Applied sciences; Exact sciences and technology; Organic polymers; Physicochemistry of polymers; Polycondensation; Preparation, kinetics, thermodynamics, mechanism and catalysts; Aniline derivative polymer; Electrochemical properties; Solution polycondensation; Molecular structure; Preparation; Tertiary amine; Soluble compound; Acid catalysis; Aldehyde; Experimental study; Redox polymer; Acetone
• ISSN: 1022-1352; 1521-3935
• DOI: 10.1002/(SICI)1521-3935(19990101)200:1<65::AID-MACP65>3.0.CO;2-S

Triphenylamine (TPA) was reacted with carbonyl compounds such as formaldehyde, butyraldehyde, benzaldehyde, and acetone in the presence of an acid catalyst. 1H and 13C NMR spectra revealed that the carbonyl compounds react only at the p‐position of TPA. The reactivity of formaldehyde with TPA is lower than that with phenol. If equal molar amounts of formaldehyde are reacted, however, TPA condensation proceeds to high molecular weight polymers, while phenol provides only low molecular weight compounds (up to 1 000). TPA‐aldehyde polymers have glass transition temperatures in the range of 135 – 176°C. These polymers show good solubility and sufficient stability after film formation.