Lanthanide–imidazole complexes as latent curing agents for epoxy resins

Abstract

AbstractImidazoles have for some time been recognized as curing agents for epoxy resins. Once the resin and the imidazole compound are mixed there is a relatively short time in which the mixture can be used, since the polymerization (curing) reaction occurs to some extent even at room temperature causing the reaction mixture to thicken. In order to circumvent this problem we have found that imidazoles can be complexed with organo‐lanthanide compounds thereby tying up the imidazole and retarding its rate of reaction in the cure of epoxy materials at ambient temperatures. When it is desired to enhance the rate of cure the temperature of the mixture is simply raised. This paper concerns studies of the epoxy cure reaction with the M(THD)3–IM series. M represents the lanthanide metals Eu, Ho, Pr, Dy, Yb, and Gd, and THD is 2,2,6,6‐tetramethyl‐3,5‐heptanedione. Cure reactions were followed by differential scanning calorimetry and in some cases by infrared spectroscopy. We have demonstrated that these organo‐lanthanide–imidazole complexes are effective thermally latent curing agents for epoxy resins. At a temperature of 150°C cure is quite rapid. In the course of these studies it has also been determined that there is an inverse correlation between the lanthanide ionic radius in the complex and the temperature at which the cure reaction occurs. Thus the Yb compound, where the imidazole is most strongly bound, cures at the highest temperature and Pr, where imidazole is bound most weakly, at the lowest. Consistent with these facts is the observation that the Yb compound also gives the longest latency period when mixed with epoxy resin.