Thermotropic Behavior of Cholesterol-Linked
Polysaccharides
V. A. E. SHAIKH,
1
N. N. MALDAR,
1
S. V. LONIKAR,
1
C. R. RAJAN,
2
S. PONRATHNAM
2
1
Shivaji University Centre for Postgraduate Studies, Medical College old Campus, Solapur 413003, India
2
Division of Chemical Engineering, National Chemical Laboratory, Pune 411008, India
Received 21 August 1997; accepted 24 March 1998
ABSTRACT: Cholesterol-linked polysaccharides were prepared by reacting monocho-
lesterylsuccinate (ChMS) with cellulose acetate [AC; degree of substitution (DS) 1.00,
1.80, and 2.33], ethyl cellulose (EC; DS 2.46), starch, and hydroxyethyl starch (HES;
molar substitution, 0.05– 0.07). The degree of ChMS substitution ranged from 0.27 to
1.29. The polymers were characterized by IR, NMR, DSC, and hot-stage coupled
polarizing microscopy. Polymers with a higher DS of ChMS showed a thermotropic
liquid crystalline behavior. © 1998 John Wiley & Sons, Inc. J Appl Polym Sci 70: 195–201, 1998
Key words: thermotropic; polysaccharides; cholesterol; cellulosics; polarizing optical
microscopy
INTRODUCTION
Cellulosic polymers display liquid crystalline
properties. The first cellulose derivative reported
to exhibit lyotropic liquid crystalline behavior
was hydroxypropyl cellulose.
1
Several reviews on
cellulosic liquid crystals have appeared.
2–4
Hy-
droxypropyl cellulose
5
and its derivatives
6–8
have
been shown to be thermotropic materials. Re-
cently, mesophase formation in hydroxyethyl cel-
lulose acetate
9
and fully decanoated cellulose
10
was reported. Tri-o-benzylcellulose, prepared in a
homogeneous medium, with a DP w of 130 showed
characteristics of a thermotropic liquid crystal.
11
In all these investigations, the substituents in-
troduced onto the cellulose backbone are nonme-
sogenic. Here, we report on the synthesis and
mesomorphic behavior of monocholesterylsucci-
nate derivatives of acetyl cellulose (AC), ethyl
cellulose (EC), starch, and hydroxyethyl starch
(HES). The effect of the degree of substitution
(DS) on the mesomorphic behavior of a monocho-
lesterylsuccinate derivative of hydroxyethyl cellu-
lose forms the basis of another communication.
Cholesterol is important in the field of liquid crys-
tals and biological materials. Side-chain liquid
crystalline polymers where cholesterol is used as
mesogenic units have been reported.
12–14
It is not
necessary that the mesogenic group is present at
every repeating unit as is indicated by the real-
ization of a mesophase in the copolymer of the
cholesteryl monomer with nonmesogenic mono-
mers.
14
Combined liquid crystalline polymers
containing mesogenic units in both the main
chain and side chains with the side chains at-
tached to rigid rodlike polymer main chain are
known.
15
This suggests that introducing a bulky
substituent onto a semirigid backbone would not
necessarily preclude mesophase formation. The
intended application for the monocholesterylsuc-
cinate derivatives of polysaccharide is as bile acid/
cholesterol sequestrants. Many studies describe
the use of a variety of carbohydrate-derived ma-
terials including hydroxypropyl methyl cellulose
Correspondence to: S. V. Lonikar.
Contract grant sponsor: Department of Science and Tech-
nology (DST), New Delhi; contract grant number: SP/S1/G-72/
90.
Journal of Applied Polymer Science, Vol. 70, 195–201 (1998)
© 1998 John Wiley & Sons, Inc. CCC 0021-8995/98/010195-07
195