SYNTHESIS OF GLYCIDYL AND THIOGLYCIDYL ETHERS OF DIACETYLENE SERIES AND THEIR USE AS A MODIFIER OF PHENOL-FORMALDEHYDE OLIGOMERS

It has been shown that the chlorine-containing unconjugated enyne alcohols react with epichlorohydrin in the presence of boron trifluoride etherate with formation of chlorohydrines, which further without their isolation, under the action of potassium hydrochloride are dehydrochlorinated with formation of the corresponding glycidyl ethers. Under the action of an alcoholic solution of potassium hydroxide at temperature of 75-80 °С on synthesized chlorine-containing ethers the dehydrochlorination reaction on double С=С bond proceeds and glycidyl ethers of 1,4-diine series are formed. It has been revealed that the synthesized glycidyl ethers are the very reactive compounds. In patricular, it has been shown that the ethers of 1,4-diine series with the participation of oxirane ring undergo the reaction with thiurea medium of methanol at 30-35 °С, forming the corresponding tyrants. The data of IR- and NMR-spectra of the prepared compounds have been presented and their modifying properties in relation to phenol-formaldehyde oligomers in acidic and alkaline media have been revealed. The prepared modified oligomers are the products of liquid-viscous consistency, soluble in acetone, tetrahydrofuran, dimethyl formamide and dioxane. It has been proved by the carried out analyses that the prepared PhFOs, modified by glycidyl and thiglycidyl ethers of diacetylene series are not mechanical mixtures of phenol, formaldehyde and modifier. On the basis of obtained results the formation mechanism of modified resol and novolac PhFO has been also revealed. It has been established that the physical-chemical and physical-mechanical parameters of the prepared phenol-formaldehyde oligomers modified by modifiers proposed by us, in comparison with unmodified ones, are improved. From the proposed diglycidyl and thiodiglycidyl ethers for the modification of PhFO the best results on all parameters are achieved at modification with thioglycidyl ether of diacetylene series.