1070-4272/02/7502-0276 $27.00 C 2002 MAIK [Nauka/Interperiodica]
Russian Journal of Applied Chemistry, Vol. 75, No. 2, 2002, pp. 276!280. Translated from Zhurnal Prikladnoi Khimii, Vol. 75, No. 2, 2002,
Original Russian Text Copyright + 2002 by Solovskii, Pavlov, Korneeva, Harding, Denisov, Nikol’skaya.
AND POLYMERIC MATERIALS
Synthesis of N-Vinylpyrrolidone!Crotonic
Acid!2-Hydroxyethyl Methacrylate Terpolymers
as Carriers of Biologically Active Substances
M. V. Solovskii, G. M. Pavlov, E. V. Korneeva, S. E. Harding,
V. M. Denisov, and N. V. Nikol’skaya
Institute of Macromolecular Compounds, Russian Academy of Sciences, St. Petersburg, Russia
Research Institute of Physics, St. Petersburg State University, St. Petersburg, Russia
National Centre of Macromolecular Hydrodynamics, Nottingham University, Nottingham, UK
Received November 2, 2001
Abstract-Water-soluble N-vinylpyrrolidone3crotonic acid32-hydroxyethyl methacrylate terpolymers, po-
tential polymeric carriers for biologically active substances, were prepared. The composition of the terpoly-
mers was determined, their chemical structure was confirmed, and their hydrodynamic characteristics and
structural features in aqueous solutions were studied.
N-Vinyl-2-pyrrolidone (VP) terpolymers containing
two types of monomeric units with reactive functional
groups are of indubitable interest for development of
polymeric carriers for biologically active substances
(BASs) . Such terpolymers can serve as a basis for
preparing hydrophilic polymers with polyfunctional
activity by covalent (or ionic and covalent) binding of
two BASs with different mechanisms of the biological
effect. It is interesting to consider in this respect VP
terpolymers I containing carboxy and primary hy-
In this work, we prepared and studied such terpoly-
mers. These substances were synthesized by ternary
radical copolymerization of VP with crotonic acid
(CA) and 2-hydroxyethyl methacrylate (2-HEMA). The
interest in 2-HEMA is due to the fact that polymers
based on it (hydrogels) are biologically compatible
with a living body and are used for immobilization of
various BASs and fabrication of contact lenses .
At the same time, VP3CA copolymers are also used
for modification of various BASs [7, 8]. Furthermore,
CA acts as a chain-terminating agent in the polymeriz-
ing monomer mixture.
The kinetics of terpolymerization of VP (M
) and 2-HEMA (M
) was studied in ethanol
at 343 K; the monomer molar ratio was [M
] = 65.5 : 14.5 : 20.0, and the concentration of the
initiatior, azobis(isobutyronitrile) (AIBN), 1.5 wt %.
The total initial concentration of the monomers was
20 wt %. For comparison, we studied under the same
conditions the binary copolymerization of VP with
2-HEMA at the molar ratio [M
] = 80 : 20.
Copolymerization of VP with 2-HEMA under these
Fig. 1. Conversion a vs. time t in copolymerization of
monomers in ethanol at 343 K in the presence of 1.5 wt %
AIBN. Initial concentration of the monomers 20 wt %.
Copolymer and molar ratio of monomers: (1)VP32-HEMA,
] = 75 : 25; (2, 3)VP3CA32-HEMA, [M
] = 65.5 : 14.5 : 20.0 and 77.0 : 14.5 : 8.5,