1070-4272/04/7710-1675 C 2004 MAIK [Nauka/Interperiodica]
Russian Journal of Applied Chemistry, Vol. 77, No. 10, 2004, pp. 1675!1678. Translated from Zhurnal Prikladnoi Khimii, Vol. 77, No. 10, 2004,
Original Russian Text Copyright + 2004 by Nikitina, Zhunusova, Shoinbekova, Mukhitdinova, Ergozhin.
AND POLYMERIC MATERIALS
Radical Copolymerization of Acrylic Acid with Derivatives
of Monoethanolamine Vinyl Ether and o- and p-Chloranil
A. I. Nikitina, G. N. Zhunusova, S. A. Shoinbekova, B. A. Mukhitdinova, and E. E. Ergozhin
Bekturov Institute of Chemical Sciences, Ministry of Education and Science of the Republic of Kazakhstan, Almaty, Kazakhstan
Received July 20, 2004
Abstract-Radical copolymerization of derivatives of monoethanolamine vinyl ether and o- and p-chloranil
with acrylic acid was studied. The parameter p for this system was determined by the Shtraikhman analytical
graphic method; the copolymerization constants, Alfrey3Price specific activity and polarity parameters,
probabilities of formation of various unit sequences in the macromolecular chain, lengths of sequences of
similar monomeric units, and Harwood block structure parameters were calculated.
Although widely diverse synthetic ion exchangers
are available today, improving their production pro-
cesses and physicochemical characteristics and lover-
ing of the production cost remain problems of current
Previously, we have reported data on preparation of
new quinoid derivatives of monoethanolamine vinyl
ether (MEAVE)  and on their radical homopoly-
merization and copolymerization with available vinyl
monomers . In contrast to MEAVE, which shows
virtually no tendency toward polymerization , and
to quinones, which inhibit the polymerization, the
redox monomers synthesized fairly readily enter rad-
ical homoand copolymerization. However, quinones
differ in reactivity, depending on their structure.
The use of o- and p-chloranils for preparing redox
ion exchangers is of large interest due to strong oxida-
tive power of these compounds containing four chlo-
rine atoms; the activity and redox potential of o-qui-
nones are higher than those of their p-isomers .
In this study, we analyzed how the chemical struc-
ture (namely, position of carbonyl groups) affects the
reactivity of redox monomers in copolymerization
with acrylic acid (AA).
(mp 1253130oC) was prepared as described in .
(mp 289oC) was purchased from Aldrich and used
without additional purification.
Redox monomers (C
) prepared accord-
ing to  were cherry-lilac powders. The elemental
composition and some physicochemical properties
of derivatives of MEAVE and o- and p-chloranils
(MEAVE31,2-CA and MEAVE31,4-CA), M 296.53,
are listed in Table 1.
Azobis(isobutyronitrile) (AIBN) was recrystallized
from absolute methanol, mp 1023103oC.
Table 1. Elemental composition and selected physicochemical properties of new redox monomers
³ C ³ H ³ N ³ Cl ³³³
ÃÄÄÄÄÄÄÄÄÁÄÄÄÄÄÄÄÄÁÄÄÄÄÄÄÄÄÁÄÄÄÄÄÄÄÄ´ ³ ³Monomer ³³r,gcm
³ mp, oC ³ Yield, %
³ % ³³³
³ 2.70 ³ 4.73 ³ 35.90 ³³³
MEAVE-1,2-CA ³ ÄÄÄÄÄ ³ ÄÄÄÄÄ ³ ÄÄÄÄÄ ³ ÄÄÄÄÄ ³ 3 ³ 1383140 ³ 43.60
MEAVE-1,4-CA ³ ÄÄÄÄÄ ³ ÄÄÄÄÄ ³ ÄÄÄÄÄ ³ ÄÄÄÄÄ ³ 0.6111 ³ 1683170 ³ 67.10
Numerator, calculated; denominator, found.