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Side reactions of phenylisocyanate in N , N ‐dimethylacetamide
Author(s) -
Matsui Toshimi,
Kamatani Hiroyoshi,
Arimatsu Yoshikazu,
Kaji Atsushi,
Hattori Kazuhiro,
Suzuki Hajime
Publication year - 1991
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.1991.070420910
Subject(s) - phenylisocyanate , dimethylacetamide , isocyanate , chemistry , polymer chemistry , side chain , diphenylmethane , solvent , organic chemistry , polyurethane , polymer , catalysis
Side reactions of isocyanate groups in N,N ‐dimethylacetamide (DMAC) were studied. Although 4,4′‐diphenylmethane diisocyanate (MDI) in DMAC was stable and no changes occurred at 3°C, the isocyanate content decreased and a gel was finally formed at 40°C. Using phenyl isocyanate (PI) as a model compound of MDI, the identification of PI side‐reaction products in DMAC were studied. From these experiments, the following five products were identified; (1) 1,3‐diphenylurea (DPU), (2) 1,3‐diphenyl‐5‐phenylcarbamyl‐6‐dimethylaminouracil (PUR), (3) 1,3,5‐triphenylbiuret (TPB), (4) triphenyl‐ s ‐triazine‐2,4,6‐trione (TTT), and (5) 1,1‐dimethyl‐3‐phenylurea (DMPU). Among these identified products, the novel side reaction product PUR, which was formed between PI and DMAC as solvent, was found along with TPB and TTT, which were already known to cause three‐dimensional network formation.