Syntheses of Polymers Containing 1, 2-Diphenoxyethane

Abstract

Syntheses of polymers using 1, 2-diphenoxyethane (1) as the starting naterial are descrided. (1) was prepared in an excellent yield by the condensation of phenol with ethylene bromide in the prsence of NaOH using dimethyl sulfoxide (DMSO) -H2O medium1, 2-Diphenoxyethane-p, p'-diethylene oxide (4) was obtained by the attack of sulfonium-ylide on p, p'-diformyl-1, 2-diphenoxyethane (3), which was prepared by the condensation of p-hydroxybenzaldehyde with ethylene bromide.p, p'-Dichloromethyl-1, 2-diphenoxyethane (2), obtained by the dichloromethylation of (1) with formaldehyde and HCl, was converted to bisphenol (5), and (5) was converted further to polyester (6) and diglycidyl ether (7).(2) was treated with triphenylphosphine to give quaternary phosphonium salt (10), which was reacted with (3) as an example of Wittig reaction.Furthermore, polyether (8) or polysulfide (9) was synthesized by the condensation of (2) with phenolphthalein or Na2S p, p'-Dicyanomethy1-1, 2-diphenoxyethane (12), derived from (2), was treated with formaldehyde to give dimethylol compound (14) and a cross-linked polymer (15).Polyester (13) was also obtained by the reaction of (12) with 1, 6-hexanediol.Lastly, (12) was condensed with (2) in the presence of potassium tert-butoxide in tert-butyl alcohol to give a polymer (16) which has no solvent.