Study of the Condensation Reaction of 2-Allylphenol With Formaldehyde and Methylamine and the Functional Properties of the Obtained Products

Abstract

By triple condensation of 2-allylphenol with formaldehyde and methylamine (at a ratio of 1:1:1 and 1:2:1 mol, at 800C for 3 hours) a number of compounds (I-III) of various structures was prepared. It has been established that, depending on the ratio of the taken reagents, compounds of various structures are formed. By the reaction of compound I - 8-allyl-substituted 1,3-benzoxazine with HBr quaternary ammonium salt (IV) was obtained. Antimicrobial activity of 8-allyl-substituted 1,3-benzoxazine (I) and ammonium salt (IV) against microorganisms: Staphylococcus aureus NCTC 6571, Staphylococcus aureus ATCC®25923, Escherichia coli ATCC®25922, Candida albicans NSTC-3255/ATCC2091, Shigella flexneri ATCC®12022, Salmonella enterica ATCC®13076, and Aspergillus niger (aquatic isolate) was studied. It was found that compounds I and IV at a concentration of 30 mg/L in comparison with the references (amoxicillin and fluconazole) have the highest bactericidal and fungicidal properties. By thermal treatment of compound I cross-linked copolymer V was synthesized. While studying the thermal properties of copolymer V their sufficient thermal stability (up to ~4500C) was established. Copolymer V also has a sorption property for the extraction of uranyl ions from aqueous systems (the degree of extraction at pH 7 is ~70%, the sorption capacity – 178 mg/g). The structures of the obtained compounds were confirmed by IR and NMR spectroscopy