PREPARATION OF AMPHIPHILIC POLYISOBUTYLENES-B-POLYETHYLENAMINES BY MANNICH REACTION .2. STUDY OF MANNICH REACTION ON MODEL SYSTEMS

The study of the reactions which take place when alpha-methyl-omega-phenolpolyisobutylene is polycondensed with triethylenetetramine (TETA) and para-formaldehyde (Mannich condensation) is carried out on model systems including monofunctional [ 2,4-di-tert-butylphenol (A), dibutylamine (B), and dodecylamine (B')] and difunctional reactants [4-tert-butylphenol (A') and 1,6-hexamethylenediamine (B'')]. With the exception of the A + B system which gives only Mannich condensation, all the systems including at least one difunctional reactant are characterized by side reactions which accompany the Mannich condensation. However, when one of the compounds is monofunctional (A + B'; A'+ B') only nonpolymeric molecules are formed; their structures were determined by H-1- and C-13-NMR spectroscopy. On the other hand, when both reactants are bifunctional (A' + B''; A' + TETA) polymers are formed whose monomer units were identified by comparison of their spectra with those of the nonpolymeric molecules.