By S. S. Labana (Auth.)
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E. Sepulveda, ACS Polym. , 16 (1), 628 (1975) . 20. G. Pifferi, L. Fontaneila, E. Ocelli, R. Monguzzi, J^. Hetero. , 9, 1209 (1972). 21. R. Pschorr and H. , 38, 2067 (1905). 22. H. Ulrich, Brit. 1,153,261, May 1969; U. S. 3,488,376; Fr. 1,554,979 to Upjohn Co. 23. Y. Iwakura, Chem. High Polym (Japan), 2, 305 (1945); CA 44, 5103 (1950). 24. C. F. H. Allen and E. W. Magder, J_. Hetero. , 6, 349 (1969). CONTROLLABLE REACTIVITY EPOXY RESIN HARDENERS Mark Markovitz General Electric Company Epoxy resin hardeners having a wide reactivity range were prepared from organometallic compounds plus a phenolic compound or a phenolic resin.
The carbonyl absorption matches that of the linear model phenyl carbanilate rather than that of 2-benzoxazolinone, suggesting the structure of Polymer I. 0 and 10μ is very dissimilar to that of three carbamate models: 2benzoxazolinone, phenyl carbanilate, and poly-p-phenylene urethane (Polymer VI discussed later). (Oj^C=0
Polymer III Again, the Curtius route formed predominately cyclic carbamate - in this case l,3-benzoxazin-2-one. Only 6% of soluble polymer III was formed upon decomposition of the azide at 80°. Polymer III prepared in this way contained some isocyanurate, but no urea linkages. Because of overlapping absorptions, isocyanurate cannot be quantitated and diarylmethane cannot be detected in the presence of carbamate linkages of the N-benzyl-O-phenyl type. CO CJ1 TABLE 6 . ^Heating II,bulk 176-185° II,reflux quinoline (237°) 2 2 N of 10° per 490 378 312 260 323 485 360 246 275 525 427 219 465 330 210 minute 55 45 70 77 66 6 238 1 228 220 210 196 185 Residue 400°(%; at 400°(%) of 33l-Benzoxazin-2-one Temp, at wt.