| In this work several new biocidal materials were produced. A new synthetic pathway was developed in order to synthesize asymmetric 1,3-dichloro-2,2,5,5-tetra- substituted-imidazolidin-4-one monomeric biocides. The constructed route consisted of five synthetic steps. First, a symmetric 2,2,5,5-tetrasubstituted-imidazolidin-4-thione was produced. This compound was subjected to acid hydrolysis forming an acyclic aminothioamide. The aminothioamide was then condensed with a ketone to produce the desired cyclic asymmetric 2,2,5,5-tetrasubstituted-imidazolidin-4-thione. The last two steps involved oxidation to the corresponding 2,2,5,5-tetrasubstituted- imidazolidin-4-one, and finally chlorination to the desired asymmetric 1,3-dichloro- 2,2,5,5-tetrasubstituted-imidazolidin-4-one analog which displayed extraordinary biocidal activity.; A biocidal polymer was produced by reacting 2,2,5,5-tetramethylimidazolidin-4-one with para-vinylbenzyl chloride, polymerizing the resulting monomer, and then chlorinating the polymer, imparting to it biocidal properties. A biocidal copolymer was also synthesized in this work. 5-methyl-5-(4'-vinylbenzyl)barbituric acid was produced by synthesizing 5-methylbarbituric acid salt and reacting it with para-vinylbenzyl chloride. The resulting monomer was then copolymerized with acrylonitrile producing a copolymer which upon chlorination displayed antibacterial activity.; Finally, a biocidal elastomer was produced by chemical modification of a commercially available thermoplastic elastomer. The thermoplastic elastomer was a block copolymer consisting of polystyrene end blocks and a rubber midblock of polyethylene and polybutylene. This thermoplastic elastomer was made biocidal by a three step synthetic process. First, a Friedel Crafts acylation reaction was performed to introduce a ketone functionality to the para position of the benzene ring in the polystyrene portion of the block copolymer, followed by hydantoin ring formation at the same position, and finally, chlorination of the attached hydantoin moiety to produce biocidal activity in the material. |
