Pendant adamantyl poly(ether imide)s: synthesis and a preliminary study of properties

Adamantyl-substituted dihydroxybenzenes were prepared by reacting 1-bromoadamantane with dihydroxybenzenes. The major products were 4-(adamantyl-l)-1,2-dihpdroxybenzene, 4-(adamantyl-1)-1,3-dihydroxybenzene and 2-(adamantyl-1)-1,4-dihydroxybenzene. The first was not isomerically pure and the third was contaminated with a small proportion of di(adamantyl-1)-1,4-dihydroxybenzene. These adamantyl-substituted diols were converted to bis(ether anhydride)s. Poly(ether imide)s were prepared by reacting the adamantyl-substituted bis(ether anhydride)s with aromatic diamines. Solubilities and thermal transition temperatures of the poly(ether imide)s were compared with data for poly(ether imide)s with other alkyl-substituents and with main-chain adamantyl units. (C) 1999 Elsevier Science Ltd. All rights reserved.