Synthesis of new ferrocene containing diamines and their use in epoxy resins
摘要:
Treatment of 4,4-bis(ferrocenyl)heptane-1,7-diol (1) with benzenesulfonyl chloride afforded after workup and crystallization, 4,4-bis(ferrocenyl)-heptane-1,7-bis(benzenesulfonate) (2) in 67% isolated yield. Compound 2 was reacted with sodium 3-aminophenoxide or sodium 4-aminophenoxide in DMF to afford 1,7-bis(3-aminophenoxy)-4,4-bis(ferrocenyl)heptane (3a) (80%) and 1,7-bis(4-aminophenoxy)-4,4-bis(ferrocenyl)heptane (3b) (88%), respectively. Compounds 3a and 3b were copolymerized with methylenedianiline (MDA) and Epon (R) Resin 828 to afford fully cured epoxy resins. We found 3b to cure faster than 3a by DSC analysis. Samples of the cured resins with 20 mol% of 3a and without ferrocene monomer were prepared with engineered defects (polypropylene letters 3 mm thick) and subjected to X-ray analysis. The samples containing ferrocene show good contrast of the defects under mild X-ray imaging conditions; whereas, non-ferrocene containing samples did not allow detection of the engineered defects. (C) 2001 Elsevier Science B.V. All rights reserved.