Russian Journal of Applied Chemistry, 2009, Vol. 82, No. 10, pp. 1882−1889.
Pleiades Publishing, Ltd., 2009.
Original Russian Text
E.V. Chernikova, P.S. Terpugova, A.N. Filippov, E.S. Garina, V.B. Golubev, A.I. Gostev, E.V. Sivtsov, 2009, published in Zhurnal
Prikladnoi Khimii, 2009, Vol. 82, No. 10, pp. 1730−1737.
AND POLYMERIC MATERIALS
Controlled Radical Polymerization of N-Vinylpyrrolidone
and N-Vinylsuccinimide under the Conditions of Reversible
Chain Transfer by the Addition–Fragmentation Mechanism
E. V. Chernikova
, P. S. Terpugova
, A. N. Filippov
, E. S. Garina
, V. B. Golubev
A. I. Gostev
, and E. V. Sivtsov
Lomonosov Moscow State University, Moscow, Russia
St. Petersburg State Institute of Technology, St. Petersburg, Russia
Received June 30, 2009
Abstract—Regular trends in controlled radical polymerization of N-vinylpyrrolidone and N-vinylsuccinimide
by the mechanism of reversible chain transfer in the presence of a series of dithiobenzoates and trithiocarbonates
were studied. The possibility of preparing soluble poly-N-vinylsuccinimide in concentrated solutions using benzyl
benzodithioate as reversible chain-transfer agent was demonstrated.
Polymers based on N-vinylpyrrolidone (VP) and
N-vinylsuccinimide (VSI) ﬁ nd wide use as hydrophilic
nontoxic materials in medicine and biology. They are
permitted for use in contact with physiological media
of a living body and can perform various functions as
components of materials for medicobiological purpose
[1–3]. Aqueous solutions of poly-N-vinylpyrrolidone
(PVP) are used as blood substitute and as a base for
infusion and peroral preparations exhibiting high
sorption properties, binding toxic substances, and
favoring their rapid elimination from the living body.
N-Vinylpyrrolidone copolymers act as auxiliary substances
in the development of drug forms (thickeners for pastes
and ointments, stabilizers for emulsions and suspensions,
substitutes of fat bases and Vaseline, tablet shells, etc.).
Complexes of poly-N-vinylpyrrolidone with iodine are
used in antiseptic preparations. Polymers based on VP are
used for modiﬁ cation of anionic surfactants exhibiting
high bactericidal activity . VP can be successfully used
in the development of polymeric derivatives of antibiotics
for decreasing their toxicity, improving the solubility and
pharmacokinetics, and controlling the rate of supply into
the living body . A number of copolymers of VP with
ionic comonomers exhibits intrinsic antimicrobial activity
and exerts immunostimulating and immunomodulating
VSI-based polymers also show promise for medicine
[3, 6]. Base hydrolysis allows poly-VSI (PVSI) to be
readily converted to poly(N-vinylamidosuccinic acid)
salt, which, in turn, can be converted to the acid form
with a cation exchanger (KU-2) (Scheme 1).
The thus modiﬁ ed homo- and copolymers of VSI are
capable of ionic binding of antibiotic bases. Depending
on the comonomer, they can be water-soluble or soluble
only in organic media. In the ﬁ rst case, they are used as a
polymeric matrix for prolonging the action of drugs ,