Journal of Polymer Science Part A: Polymer Chemistry, Vol.48, No.4, 845-851, 2010
Three-Component Polyaddition of Diamines, Carbon Disulfide, and Diacrylates in Water
The three-component polyaddition of diamines, carbon disulfide (CS2), and diacrylates in water was successfully achieved without the use of a surfactant or catalyst. Appropriate reaction conditions (i.e., reaction temperature, reaction time, and CS2 feed) enabled the polyaddition of 1,3-di-4-piperidylpropane (1a), CS2, and 1,6-hexanediol diacrylate (2a) to afford the corresponding poly(dithiourethane-amine) containing 83% of dithiourethane units in 84% yield. Polyaddition of other monomers also proceeded under the optimum conditions to afford various poly(dithiourethane-amine)s. Unsuccessful results for polyaddition in organic solvents such as toluene, tetrahydrofuran, and N,N-dimethylformamide revealed that the polyaddition is accelerated in water. The obtained poly(dithiourethane-amine)s adsorbed Au (III) efficiently under acidic conditions, due to the strong interaction of the thiocarbonyl sulfur in the dithiourethane unit with Au (III). The poly(dithiourethane-amine)s also showed selective adsorption for Au (III) from a mixture of metal ions [Au (III), Fe (III), Mn (II), and Zn (II)], which indicates their potential utilization for the collection of gold. (C) 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 845-851, 2010