A model study for coatings containing hexamethoxymethylmelamine

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    The crosslinking chem. of hydroxy-functional polymers and hexamethoxymethylmelamine (I) was studied using a model reaction. The transetherification of optically active monofunctional alcs. and I was monitored with polarimetry and 1H-NMR. The reaction rate consts. for both the forward and the backward reaction of the p-toluenesulfonic acid [104-15-4] catalyzed alcoholysis were detd. Primary [(l)-2-methyl-1-butanol [1565-80-6]] and secondary [(d)-2-octanol [6169-06-8]] alcs. showed the same reaction rate and activation energy (Ea = 96 kJ/mol) for the forward reaction. However, the backward reaction in the equil. was considerably slower for the primary alcs. than for the secondary alc., with activation energies of Ea= 96 and 79 kJ/mol, resp. When 4-dodecylbenzenesulfonic acid pyridine salt [105093-19-4] was used as a catalyst, the Ea increased from 97 to 116 kJ/mol in the case of the primary alc. In concd. aprotic solns. the reaction order in acid was 2.5. The same order in acid was found for the alcoholysis of acetaldehyde di-Et acetal [105-57-7]. All the results strongly supported the statement that the crosslinking reaction proceeded by an SN1 mechanism. [on SciFinder (R)]
    Original languageEnglish
    Pages (from-to)2199-2208
    Number of pages10
    JournalJournal of Polymer Science, Part A: Polymer Chemistry
    Issue number9
    Publication statusPublished - 1986


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