Reactions of diaminoalkanes with bismaleimides: Synthesis of some unusual polyimides

✍ Scribed by Jerry E. White; Mark D. Scaia; Deborah A. Snider

• Book ID: 102733190
• Publisher: John Wiley and Sons
• Year: 1984
• Tongue: English
• Weight: 505 KB
• Volume: 29
• Category: Article
• ISSN: 0021-8995
• DOI: 10.1002/app.1984.070290317

✦ Synopsis

Michael additions of the secondary diamines N,W-dimethyl-l,6-hexanediamine (14) or piperazine to the electrophilic carbon-carbon double bonds of N,N'bismaleimido-4,4'-diphenylmethane (2) or N , Nbismaleimido-l,8-octane (4) afford four unusual, high-molecular-weight (qinh = 0.49-2.16 dL/g) polyimides (10-13). The most interesting of these, polymer 12 (the product of 4 and 14), is a tough elastomeric resin with a glass transition temperature (T,) near 0°C; in contrast, 10,11, and 13 exhibit Tg > 86°C. Freshly prepared 12 is soluble and thermoplastic (12 is readily compression molded a t llO"C), but the bulk polymer crosslinks slowly under ambient laboratory conditions and eventually (48 days) becomes insoluble, while 10, 11, and 13 remain soluble indefinitely. Along with further comparisons of the properties of 10-13, details of the synthesis and characterization of these new polyimides are described. Also discussed are reactions of bismaleimide 2 with 1,6-diaminohexane, which unlike the formation of linear 10-13, generate crosslinked, insoluble products.