<i>N</i>‑Methylmelamines: Synthesis, Characterization, and Physical Properties
Manuela List
Helmut Puchinger
Herbert Gabriel
Uwe Monkowius
Clemens Schwarzinger
10.1021/acs.joc.6b00355.s001
https://acs.figshare.com/articles/journal_contribution/_i_N_i_Methylmelamines_Synthesis_Characterization_and_Physical_Properties/3257179
<i>N</i>-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 <i>N</i>-methylmelamines were prepared, and reaction
progress was monitored by GC/MS. 2,4,6-TrisÂ(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 p<i>K</i><sub>b</sub> 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 p<i>K</i><sub>b</sub> 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.
2016-04-21 00:00:00
Methylmelamine
polymerization processes
melamine derivatives
solubility
GC
compound
dimethylamino groups
mass spectrometry
temperature ranges
form hydrogen bonds
novel materials
polymerization reaction
IR spectroscopy
building blocks
Physical Properties N
reaction progress
NMR
reaction conditions
melamine formaldehyde resins
p K b increase
methylamino groups
synthesis routes
polymer building blocks
point shifts
p K b values