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Preparation of a triphenylcarbinol moiety‐containing cellulose derivative and its properties
Author(s) -
Arai Kenichiro,
Kawabata Yumi
Publication year - 1995
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.1995.021960705
Subject(s) - moiety , chemistry , cellulose , microcrystalline cellulose , polymer chemistry , alkali metal , amine gas treating , bromide , solvent , derivative (finance) , sodium bromide , organic chemistry , sodium , financial economics , economics
A triphenylcarbinol (TPC) moiety‐containing cellulose derivative (TPC‐Cell) was prepared by a two‐step reaction. First, microcrystalline cellulose was dissolved in SO 2 ‐diethyl‐amine‐dimethyl sulfoxide and homogeneously reacted with p ‐bromobenzyl bromide to obtain tri‐ O ‐( p ‐bromobenzyl)cellulose (BB‐Cell). Second, the BB‐Cell was reacted with butyllithium and then with Michler's ketone. The degree of substitution (DS) of the obtained ethanol‐soluble TPC‐Cell was up to 0,56. The leuco form of TPC moiety in TPC‐Cell showed a small extent of ionic dissociation in ethanol under irradiation with UV light of λ > 290 nm, accompanied by a large extent of decomposition of the structure. With additions of acid and then of alkali, the TPC structure was reversibly isomerized from the leuco form to the colored from and then from the colored from to the leuco form. However, repeated cycles of the additions of acid and alkali resulted in considerable fatigue with the number of cycles.