Synthesis of some multifunctional crosslinking agents for polyurethane

Abstract

Five compounds, Bis-(3-allyloxy-2-hydroxy-1-propoxy)diphenoxypropane (3), Bis-[3-(4-allyloxy-2-methoxy)phenoxy-2-hydroxy-1-propoxy]diphenoxypropane (7), 2,7-Bis-(3-allyloxy-2-hydroxy-1-propoxy)naphthalene (9),Bis-(3-N,N-diallylamino-2-hydroxy-1-propoxy)diphenoxypropan(11) and N,N,N',N'-tetrakis-(3-allyloxy-2-hydroxy-1-propoxy)ethylenediamine (13) were synthesized by ring opening of epoxides with nucleophiles. Compounds (7) and (10) were synthesized by the reaction of diglycidyl ether of bisphenol A (6) with eugenol (5) and diallylamine (10), respectively Compounds (3), (9), and (13) were obtained from the reaction of allyl glycidyl ether (2) with bisphenol-A (1), 2,7-dihydroxynaphthalene (8) and ethylenediamine (12), respectively. These compounds, which contain multiple hydroxyl and vinyl groups, were characterized by ¹H NMR and ¹³C NMR spectroscopy, mass spectrometry, infrared spectroscopy and elemental analysis. The reactivity of the hydroxyl and vinyl groups of compounds (3), (9), (11), and (13) were studied. It was found that the hydroxyl groups of compounds (3), (9), (11), and (13) could react with the isocyanate group of MDI to give a urethane linkage. It was also found that the vinyl groups of compounds (3), (9), (11), and (13) can undergo free radical reactions in the presence of benzoyl peroxide. These results suggest that compounds (3), (9), (11), and (13) may be used as crosslinking agents in the preparation of polyurethane elastomers.