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Reactions of diaminoalkanes with bismaleimides: Synthesis of some unusual polyimides
Author(s) -
White Jerry E.,
Scaia Mark D.,
Snider Deborah A.
Publication year - 1984
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.1984.070290317
Subject(s) - diphenylmethane , piperazine , glass transition , polymer , polymer chemistry , materials science , elastomer , carbon fibers , polyimide , alicyclic compound , diamine , electrophile , organic chemistry , chemistry , composite material , catalysis , composite number , layer (electronics)
Michael additions of the secondary diamines N , N ′‐dimethyl‐1,6‐hexanediamine ( 14 ) or piperazine to the electrophilic carbon–carbon double bonds of N , N ′‐bismaleimido‐4,4′‐diphenylmethane ( 2 ) or N , N ′‐bismaleimido‐1,8‐octane ( 4 ) afford four unusual, high‐molecular‐weight (η inh = 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 g ) near 0°C; in contrast, 10, 11, and 13 exhibit T g >86°C. Freshly prepared 12 is soluble and thermoplastic ( 12 is readily compression molded at 110°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.