Functional Polymers Bearing Reactive Azetidinium Groups: Synthesis and Characterization

• Published in: Macromolecular chemistry and physics Vol. 213; no. 5; pp. 500 - 512
• Main Authors: Chattopadhyay, Subrata, Keul, Helmut, Moeller, Martin
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 16.03.2012; WILEY‐VCH Verlag; Wiley
• Subjects: Applied sciences; azetidinium functionalized polymer; Chemical modifications; Chemical reactions and properties; Exact sciences and technology; functionalization of polymers; Organic polymers; Physical Sciences; Physicochemistry of polymers; Polymer Science; reactions of azetidinium compounds with nucleophiles; Reactions of epichlorohydrin with amines; Science & Technology; azetidinium functionalized polymer; AMINES; Reactions of epichlorohydrin with amines; functionalization of polymers; CHEMISTRY; EPICHLOROHYDRIN; reactions of azetidinium compounds with nucleophiles; Intramolecular reaction; Amino group; End group; Molecular structure; Epichlorhydrin; Telechelic polymer; Epoxy resin; Experimental study; Tetrahydrofuran polymer; Quaternary ammonium compound; Structure processing relationship; Chemical modification; Cyclization; Azetidine derivatives; Preparation; Addition reaction; Hydroxyl group; Reaction mechanism; Model reaction
• ISSN: 1022-1352; 1521-3935
• DOI: 10.1002/macp.201100480

Functional polymers with azetidinium groups in the backbone are synthesized via the reaction of aminotelechelic polymers, containing primary and secondary amino groups, with epichlorohydrin. During the reaction, the secondary amino groups are transformed into azetidinium groups and the primary amino groups are transformed into amino‐chlorohydrin, amino‐epoxide, and azetidinium groups. The formation of desired functional groups in the polymer is controlled by tuning the reaction conditions. To understand the influence of reaction conditions generating the desired functional groups, model reactions of primary and secondary amines with epichlorohydrin are studied in detail, including the influence of the mole ratio of the starting materials, effect of solvent, effect of pH, and reaction kinetics. The synthesis of functional polymers with azetidinium groups in combination with other reactive groups via the reaction of aminotelechelic polytetrahydrofuran with epichlorohydrin is reported. The secondary amino groups are transformed into azetidinium groups and the primary amino groups are transformed into amino‐chlorohydrin, amino‐epoxide, and azetidinium groups.