Phenylethynyl containing imide-silanes were prepared from aminoalkyl and aminoaryl alkoxy silanes and 4-phenyletbynylphthalic anhydride in toluene to form the imide in one step or in N-methyl-2-pyrrolidinone (NMP) to form the amide acid intermediate. Controlled molecular weight pendent phenylethynyl amide acid oligomers terminated with aminoaryl alkoxy silanes were prepared in NMP from aromatic dianhydrides, aromatic diamines, diamines containing pendent phenylethynyl groups and aminoaryl alkoxy silanes. The phenylethynyl containing imide-silanes and controlled molecular weight pendent phenylethynyl amide acid oligomers terminated with aminoaryl alkoxy silanes were used to improve the adhesion between phenylethynyl containing imide adhesives and inorganic substrates (i.e. metal). Hydrolysis of the alkoxy silane moiety formed a silanol functionality which reacted with the metal surface to form a metal-oxygen-silicon (oxane) bond under the appropriate reaction conditions. Upon thermal cure, the phenylethynyl group of the coupling agent reacts with the phenylethynyl functionality of phenylethynyl containing imide adhesives and becomes chemically bonded to the matrix. The resultant adhesive bond is more durable (i.e. hot-wet environmental resistance) than adhesive bonds made without the use of the coupling agent due to covalent bond formation between the phenylethynyl containing imide-silane coupling agent or the controlled molecular weight pendent phenylethynyl amide acid oligomers terminated with aminoaryl alkoxy silanes and both the metal substrate and phenylethynyl containing imide adhesives.
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