Three-component polyaddition of diamines, carbon disulfide, and diacrylates in water

Abstract

The three-component polyaddition of diamines, carbon disulfide (CS 2), 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-piperi- dylpropane (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(di- thiourethane-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(dithiour-ethane-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. © 2010 Wiley Periodicals, Inc.