Poly[(3‐hydroxypropyl) oxirane] and poly[(4‐hydroxybutyl)oxirane]: New hydrophilic polyether elastomers

Abstract

AbstractPreparations of poly[(3‐hydroxypropyl)oxirane] and poly[(4‐hydroxybutyl)oxirane] are described. Three routes to poly[(3‐hydroxypropyl)oxirane] are discussed, each of which involves the methanolysis of a polymeric ester. (3‐Acetoxypropyl)oxirane, [3‐(m‐chlorobenzoyloxy)propyl]oxirane, and (3‐chloropropyl)oxirane were polymerized using the AIEt3/H2O/AcAc initiator system. Poly[(3‐acetoxypropyl)oxirane] and poly{[3‐(m‐chlorobenzoyloxy)propyl]oxirane} were converted directly to poly[(3‐hydroxypropyl)oxirane] by methanolysis, the former under either acidic or basic conditions only. Poly[(3‐chloropropyl)oxirane] was first converted to poly[(3‐benzoyloxypropyl)oxirane] by treatment with tetrabutylammonium benzoate; subsequent basic methanolysis then afforded poly[(3‐hydroxypropyl)oxirane]. Poly[(3‐hydroxypropyl)oxirane] is a colorless elastomer which can be cast into tough, clear films from water or methanol. Poly[(4‐hydroxybutyl)oxirane] was prepared from poly[(4‐chlorobutyl)oxirane] by benzoyloxylation and subsequent methanolysis. Poly[(4‐hydroxybutyl)oxirane] is insoluble in water, but is hydrophilic and can be cast into tough films from methanol or dimethylsulfoxide.