T. Nishikubo et al., PHOTOGENERATION OF POLYFUNCTIONAL AMINES AND NOVEL THERMAL CURING REACTIONS OF EPOXY-RESIN AND POLYURETHANE OLIGOMER USING THESE AMINES, Journal of polymer science. Part A, Polymer chemistry, 31(12), 1993, pp. 3013-3020
Photochemical reactions of various blocked polyfunctional amines such
as bis(4-formylaminophenyl)methane (FAPM), bis(4-acetylaminophenyl)met
hane (AAPM), bis(4-benzoylaminophenyl)methane (BAPM), 2,4-diformylamin
otoluene (DFAT), m-xylene diformamide, and is[[(2-nitrobenzyl)oxy]carb
onyl]hexane-1,6-diamine were carried out to give the corresponding fre
e amines in THF solution, in epoxy resin, or in polyurethane oligomer
with terminal isocyanate groups. Photolysis of FAPM and DFAT to produc
e the corresponding polyfunctional amines such as 4,4'-methylenedianil
ine and 2,4-diaminotoluene proceeded with 80 and 75% conversions, resp
ectively, in THF solution under UV irradiation at 5 h. AAPM and BAPM a
lso produced the corresponding photo-Fries rearrangement products with
32 and 38% conversions, respectively, under the same irradiation cond
itions. The photolysis of those compounds also occurred with similar c
onversions in the epoxy resin and in the polyurethane oligomer under U
V irradiation; and the thermal curing reactions of the epoxy resin and
the polyurethane oligomer with photogenerated polyfunctional amines p
roceeded smoothly after heating at 140-degrees-C for 2 hrs. (C) 1993 J
ohn Wiley & Sons, Inc.