Publication Details (including relevant citation information):
Schechtman, Lee A. 1988 364 219-228-
Abstract: The low temperature ene reactions of 4-substituted-1,2,4-triazoline-3,5-diones (RTD) were used to modify polydiene surfaces. Hydrophilic surfaces (contact angles with water of 30-50°) were obtained on polybutadiene, polyisoprene and styrene-butadiene copolymers by first treating the polymer at room temperature with RTD (R=Ph, Me, NO2Ph, ClSO2Ph) and then with aqueous base. The use of the difunctional bis(p-1,2,4-triazoline-3,5-dione-4-ylphenyl)methane, (TD)2DPM, also produced hydrophilic surfaces. However, except for the (TD)2DPM treated surfaces, the hydrophilicity of the treated surfaces decreased after 5-10 days. The (TD)2DPM surfaces are presumably crosslinked and remain hydrophilic for at least one year. The degree of reaction, as indicated by contact angle measurements, obtained under these heterogeneous reaction conditions suggest that the relative reactivity of the various RTDs and polydienes parallel the analogous reactions under homogeneous conditions. An ESCA study of ClSO2PhTD treated surfaces confirms that the RTD is a surface species. The transformations of the surface species upon treatment with warm water and then aqueous base, -SO2Cl → -SO3H → -SO3-, were also substantiated by ESCA.
Address (URL): http://dx.doi.org/10.1021/bk-1988-0364.ch016