o-, mand p-aminobenzotrifluoride have been converted into 7-, 4-and 5-trifluoromethylisatin, respectively, through Derivatives of the isatins Two additional trifluoromethyl compounds, 5,7-bis-( trifiuoromethy1)-quinoline and m-trifluoromethy1-N-the corresponding isonitrosoacetanilides, by reactions analogous to those of unsubstituted aniline. were prepared. phenylglycine were prepared from 3,5-bis-( trifluoromethy1)-aniline and m-aminobenzotrifluoride, respectively.Aromatic and heterocyclic trifluoromethyl compounds, particularly those related to ortho and para substituted benzotrifluorides, have not been extensively studied. Normal methods of introducing the trifluoromethyl group into a heterocyclic compound could be expected to decompose all but the most stable rings.Among the heterocyclic compounds of this type may be mentioned the quinoline derivatives prepared by Andersag, Breitner and Jung2 and by Gilman and c o -~o r k e r s ,~ 4-Trifluoromethylisatin-3-( 2 ,4-dinitro)-phenylhydrazone was made from the isatin and 2,4-dinitrophenylhydrazine,
SynopsisPrevious studim by Black and Blomquist on the degradative failure of polymer-metal adhesive bonds have shown that composite failure depends largely on the type of metal substrate employed. In the work reported herein, metal powders of high surface area have been employed to maximize the metal-polymer interface. The composite systems studied consisted for aluminum and iron with polycondensates of bisphenol A-diglycidyl ether, phenol-formaldehyde and poly-2,2'-(m-phenylene)-5,5'-bibenimidazole. The composites were prepared in the absence of air and thermally degraded in a time-offlight mas3 spectrometer while t,he degradation products were continuously monitnred from mass 1 to 200. In the polymer and polymer-metal systems investigated, iron accelerated the decomposition of all polymers studied. This was determined by plotting m/e against degradation temperature for the more common m a s peaks such as hydrogen and carbon monoxide for the carbon-hydrogen-xygen-containing polymer and hydrogen cyanide and ammonia for the carbon-hydrogen-nitrogen-containing polymer. This technique offers promise in determining the nature of the interface as well as the effect of the interface on polymer degradation.
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