jo6b00355_si_005.cif (12.91 kB)
N‑Methylmelamines: Synthesis, Characterization, and Physical Properties
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posted on 2016-04-21, 00:00 authored by Manuela List, Helmut Puchinger, Herbert Gabriel, Uwe Monkowius, Clemens SchwarzingerN-Methylmelamines have recently gained importance as valuable
compounds for manufacturing modified melamine formaldehyde resins
and other polymer building blocks. A great advantage of these polymers
is the reduction of the carcinogenic formaldehyde. Selecting the polymerization
processes (e.g., substance polymerization, polymerization in solution)
and controlling the polymerization reaction and properties of these
novel materials requires knowledge of the properties of the individual
melamine derivatives used as new building blocks. All possible permutations
of N-methylmelamines were prepared, and reaction
progress was monitored by GC/MS. 2,4,6-Tris(dimethylamino)-1,3,5-triazine
was prepared to complete the series; this is, however, also a possible
byproduct in various synthesis routes. The reaction conditions were
optimized to obtain high yields of each derivative with the highest
possible purity. The substances were characterized by NMR and IR spectroscopy,
mass spectrometry, elemental analysis, and single-crystal X-ray diffraction.
In addition, physical properties, such as solubility, melting points,
and pKb values, were determined. The number
of amino-, methylamino-, and dimethylamino groups has a significant
effect on these properties. In summary, we found that by increasing
the number of amino- and methylamino groups, solubility and pKb increase. With increasing number of amino
groups, the compounds tend to form hydrogen bonds, and thus, the melting
point shifts to higher temperature ranges where they start to decompose.
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Methylmelaminepolymerization processesmelamine derivativessolubilityGCcompounddimethylamino groupsmass spectrometrytemperature rangesform hydrogen bondsnovel materialspolymerization reactionIR spectroscopybuilding blocksPhysical Properties Nreaction progressNMRreaction conditionsmelamine formaldehyde resinsp K b increasemethylamino groupssynthesis routespolymer building blockspoint shiftsp K b values
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