Thioetherglycidyl resins. I. Products of condensation of 1-mercaptomethylnaphthalene and 1,4-, 1,5-di-(mercaptomethyl) naphthalene and their mixtures with epichlorohydrin

New thioetherglycidyl resins produced by condensation of 1-mercaptomethylnaphthalene, 1,4-di(mercaptomethyl)naphthalene, 1,5-di(mercaptomethyl)naphthalene, and their mixture of 1,4- and 1,5-di(mercaptomethyl)naphthalene with epichlorohydrin were obtained. The condensation was carried out in two ways. In the first way, potassium salt of mercaptans and epichlorohydrin were used. In the second, epichlorohydrin was added to mercaptans and then the obtained chlorohydrin thioether was dehydrohalogenated by the alkaline hydroxide in water and n-butanol or isopropyl alcohol solution. The method of heterogeneous condensation of dithiol with epichlorohydrin in water and isopropyl alcohol solution proved to be the most effective. Yield, the epoxide content, and the total chlorine content for all resins were found. The structure of thioetherglycidyl resins with the highest epoxide content was determined by elementary analysis, and infrared (IR) and NMR spectra. Thermal stability of resins was studied during long controlled heating at unchanged temperature and short heating carrying the thermal gravimetric analysis (TGA) mainly in air. As follows from the studies, thioetherglycidyl resins can be cured both chemically and thermally.