of N,N-Diallyl-N,N-dimethylammonium Chloride
and Maleic Acid in Various Solvents
A. I. Vorob’eva, D. R. Sagitova, S. V. Kolesov, and Yu. B. Monakov
Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, Ufa, Bashkortostan, Russia
Received January 13, 2009
Abstract—Radical copolymerization of N,N-diallyl-N,N-dimethylammonium chloride with maleic acid in
various solvents was studied. The solvent effect on the relative activity of the monomers and the possibility of
preparing copolymers of preset composition were examined.
AND POLYMERIC MATERIALS
ISSN 1070-4272, Russian Journal of Applied Chemistry, 2009, Vol. 82, No. 6, pp. 1046–1051. © Pleiades Publishing, Ltd., 2009.
Original Russian Text © A.I. Vorob’eva, D.R. Sagitova, S.V. Kolesov, Yu.B. Monakov, 2009, published in Zhurnal Prikladnoi Khimii, 2009, Vol. 82, No. 6,
Polyfunctional water-soluble copolymers whose
macromolecules contain both cationic and anionic
groups exhibit amphoteric properties and form one of
the most interesting and promising classes of
polymers. By varying the ratio of cationic and anionic
groups, it is possible to control the total charge of the
macromolecule and hence to vary in a wide range the
service properties of copolymers such as the solubility,
molecular weight, and reactivity toward natural
compounds and in polymer-analogous transformations.
Therefore, a problem of preparing copolymers of
preset composition arises. This problem can be solved
only by studying the process in detail and revealing
factors affecting the reactivity of the comonomers.
It is known that the radical polymerization of
ionizable monomers is strongly affected by the solvent
[1–3]. Even relatively weak chemical interaction of
functional groups of monomers or radicals with the
solvent in the course of copolymerization can
significantly affect the copolymer composition and
distribution of comonomer units in the macrochain.
In this connection, it is interesting to study
copolymerization in various solvents of maleic acid
(MA) with N,N-diallyl-N,N-dimethylammonium chloride
(AMAC) whose copolymers exhibit bactericidal,
growth-stimulating, and catalytic activity [4–6].
Previously copolymerization of AMAC (М
) was studied in aqueous solution in the
presence of potassium persulfate as initiator .
Copolymerization occurs with the formation of random
copolymers, and AMAC is considerably more active
than MA. The copolymers obtained act as high-
performance hardeners in leather production .
In this study we examined the copolymerization of
AMAC with MA in various organic solvents with the
aim to find the possibility of controlling the com-
position and structure of the copolymers.
N,N-Diallyl-N,N-dimethylammonium chloride was
prepared from dimethylamine and allyl chloride as
described in . Its purity was checked by elemental
analysis, analysis for the content of double bonds, and
С NMR spectroscopy. Maleic acid of analytically
pure grade was recrystallized from acetone and
vacuum-dried to constant weight. The initiator, azobis
(isobutyronitrile) (AIBN) of analytically pure grade,
was recrystallized three times from methanol and
vacuum-dried. All the chemicals used in the study
(monomers, initiator, solvents) after purification by
common procedures had the characteristics consistent
with published data.
The copolymerization was performed in organic
solvents in a vacuum in the presence of AIBN to low
conversions and was monitored gravimetrically. On
reaching a definite conversion (5–10%), the poly-