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Methylated melamines are widely used as anti-tumor drugs, insect sterilants, and as monomers for modified melamine-formaldehyde-polymers. Hydroxymethyl(methylmelamines) are metabolites of antitumor agents such as altretamine (hexamethylmelamine) and trimelamol trimethylol(trimethylmelamine)), formed by oxidation of a methyl group and subsequent elimination of formaldehyde. N-vinylmelamine derivatives offer a broad range of industrial applications, not only homopolymerization but also copolymerization with other monomers currently being under investigation. Our recent studies have used methylmelamines as building blocks for the synthesis of functional acrylyate monomers for coatings or in the synthesis of polymer additives.
In attempt to produce new melamine polymers we have prepared different functional triazine compounds for further vinylation and then polymerization. The vinylgroup is usually attached to a free NH-group – the influence of different substituents on the Nitrogen on the rate of vinylation has been investigated and found to be of great importance. All substances were produced by a single-, two- or three step synthesis using cyanuric chloride as starting material. The products were analyzed with GC, mass spectrometry, and NMR and thus full structural elucidation achieved.
At the moment copolymerization of the vinyl melamines with commercially available monomers, such as ethylene, styrene, or methylmethacrylate is being done. Depending on the selected melamine derivative basic polymerization parameters such as catalysts, concentration of reactants, temperature, solvent and reaction time have been studied and optimized.
In order to characterize these new polymer products different analytical approaches were applied. The nitrogen content, as a measure of melamine incorporation, was determined with elemental analysis (CHN). But as this method does not give structural information on the molecular level, we also have used methods such as FTIR, NMR, analytical pyrolysis, or MALDI mass spectrometry for the characterization of our copolymers.
