Lee Schechtman - Hydrophilization of Polydiene Surfaces by Low-Temperature Ene Reactions

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  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