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Carbanilation of cellulose in the paraformaldehyde–dimethyl sulfoxide solvent system
Author(s) -
Miyagi Yoshifumi,
Young Raymond A.
Publication year - 1982
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.1982.070270230
Subject(s) - cellulose , dimethyl sulfoxide , differential scanning calorimetry , chemistry , polymer chemistry , decomposition , side chain , dissolution , paraformaldehyde , solvent , phenylisocyanate , nuclear magnetic resonance spectroscopy , materials science , organic chemistry , polymer , physics , thermodynamics
Methylol cellulos carbanilate (methylol cellulose phenylcarbamate) was prepared under homogeneous conditions with phenylisocyanate following the dissolution of cellulose into the paraformaldehyde–dimethyl sulfoxide system. Previously reported procedures were utilized to control the oligo‐oxymethylene side chain length of the dissolved cellulose. Methylol cellulose carbanilates with different side chain lengths were characterized by infrared spectroscopy, proton nuclear magnetic resonance spectroscopy, and differential scanning calorimetry. The homogeneous carbanilation reaction was found to be completed with a degree of substitution of around 2.4 within 3 h at room temperature, which is substantially faster than heterogeneous carbanilation. Methylol cellulose carbanilates were found to have lower heats of decomposition (23.5–32.2 kcal/mol, depending upon the side chain length) and lower heats of decomposition temperatures (236°C) under air compared with conventional cellulose carbanilate. This suggests that the decomposition mechanism of the methylol cellulose carbanilate is through decomposition of the oligo‐oxymethylene side chains, while cellulose carbanilate decomposes by rupture of the cellulose carbamate linkage.