Synthesis of water soluble hyperbranched polyurethanes using selective activation of AB2 monomers

Macromolecules

Volumn 37, Issue 25, 2004, Pages 9418-9430

  Rannard, Steve P ^a   Davis, Nicola J ^a   Herbert, Ian ^a  

^a UNILEVER RESEARCH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; DATA REDUCTION; DENDRIMERS; ESTERS; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; POLYURETHANES; PROTONS; PYROLYSIS; SYNTHESIS (CHEMICAL); UREA;

BRANCHING; DETECTABLE REACTIONS; MODEL REACTIONS; SELECTIVE ACTIVATION;

MONOMERS;

EID: 10844249454     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma0489218     Document Type: Article

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22. During our studies of carboxamide formation, we have observed that the addition of primary amines to stirred suspensions of CDI in toluene at room temperature form clear solutions very quickly. However, when secondary amines are added at room temperature, the suspension remains unchanged, and TLC analysis of the supernatant shows no formation of carboxamde. When the suspensions containing secondary amine are heated to 50 °C, they become clear very quickly and produce carboxamide in moderate yields (>70%). Interestingly, the carboxamides that are formed from secondary amines do not readily react with alcohols to form urethanes, or with amines to form ureas, under the conditions that we have studied. This suggests that the pathway leading to possible isocyanate intermediate formation and subsequent imidazole liberation may involve the carboxamide NH proton that is not present in examples derived from secondary amines.