SYNTHESIS OF A NONIONIC POLYMER SURFACTANT FROM CYCLIC IMINO ETHERS BY THE TERMINATOR METHOD

A nonionic polymer surfactant having a hydrophilic poly(N-acylalkylenimine) segment has been synthesized from a cyclic imino ether monomer, in which a hydrophobic group was introduced by terminating the living end of the propagating polymer (“terminator method”). Monomers used for construction of the hydrophilic segment are 2-methyl- and 2-ethyl-2-oxazolines and 2-methyl-5,6-dihydro-4H-l,3-oxazine. The surfactant properties of the product polymers were evaluated by the surface tension ( ) of the aqueous polymer solution. Three kinds of terminator were employed: (i) With 2-(higher alkyl)- or 2-[3-(perfluorooctyl)propyl]-4,4-dimethyl-2-oxazoline having reduced polymerizability, the living end of the propagating polymer was terminated, followed by hydrolysis to give the nonionic polymer surfactant having a higher alkyl or 3-(perfluorooctyl)propyl group, (ii) 2-n-Octyl- or 2-n-undecyl-5-methyl-2-oxazoline was used as the terminator in a similar method, (iii) With a primary or secondary (higher alkyl)amine and (perfluoroheptyl)methylamine, the living end of the polymer was terminated, followed by deionization to produce the polymer surfactant. Using a primary (higher alkyl)amine or (perfluoroheptyl)methylamine gave a versatile method for producing effective nonionic polymer surfactants. The lowest y value via (iii) reached 19.5 dyn/cm for a polymer sample from 2-methyl-2-oxazoline monomer/(perfluoroheptyl)methylamine terminator. © 1990, American Chemical Society. All rights reserved.