ISSN 1070-4272, Russian Journal of Applied Chemistry, 2006, Vol. 79, No. 6, pp. 997!1000. + Pleiades Publishing, Inc., 2006.
Original Russian Text + A.I. Vorob’eva, M.N. Gorbunova, S.V. Kolesov, Yu.B. Monakov, 2006, published in Zhurnal Prikladnoi Khimii, 2006,
Vol. 79, No. 6, pp. 1007!1010.
AND POLYMERIC MATERIALS
Copolymerization of N-Vinylpyrrolidone
with 3-Methacryloyloxytetrahydrothiophene 1,1<-Dioxide
A. I. Vorob’eva, M. N. Gorbunova, S. V. Kolesov, and Yu. B. Monakov
Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, Ufa, Bashkorkostan, Perm, Russia
Institute of Technical Chemistry, Ural Division, Russian Academy of Sciences, Russia
Received December 13, 2005; in final form, February 2006
Abstract-Radical copolymerization of N-vinylpyrrolidone with 3-methacryloyloxytetrahydrothiophene
1,1`-dioxide in the bulk and in dimethyl sulfoxide in the range of low conversions was studied. The kinetic
features of copolymerization were examined. The relative activities of monomers and the structure and some
characteristics of the copolymers were determined.
Poly-N-vinylpyrrolidone (PVP) is of prime im-
portance among other macromolecular compounds.
A combination of practically valuable characteristics
of PVP: solubility in water and in most of organic
solvents, absence of toxicity, biological compatibility,
immune inactivity, and also clearly pronounced capa-
bility for complex formation with a wide variety of
inorganic and organic compounds and biological sys-
tems, allows use of this compound as a disintoxica-
tion agent and prolongation agent for drugs [1, 2].
Copolymers of N-vinylpyrrolidone (VP) have a still
wider set of valuable characteristics. The copolymer-
ization reactions allow modification of PVP charac-
teristics and therefore acquire growing practical im-
portance. Copolymers based on VP are components of
a great number of drugs, act as carriers of biologically
active substances, and are the base of membranes,
sorbents, coagulants, flocculants, etc. . Copoly-
mers of VP with 3-methacryloyloxytetrahydrothio-
phene 1,1`-oxide (MAHTO) can be of some interest
for medical purposes. MAHTO is nontoxic, has clear-
ly pronounced antimicrobial, antiphlogistic, and
wound-healing effects, and enters into the composi-
tion of the medicinal glue widely used in surgery for
gluing of soft tissues of a living body [8, 9]. It is well
known that MAHTO is highly active in radical homo-
and copolymerization with vinyl monomers, methyl
methacrylate, methacrylic acid, and styrene [10, 11].
There are no published data on copolymerization of
MAHTO with VP; at the same time, it is our opinion
that copolymerization of VP with MAHTO could
widen the set of valuable characteristics and the range
of application of copolymers based on VP in medicine
Our aims were to study the copolymerization of
VP with MAHTO, namely, to determine the activities
of monomers and to examine the kinetic features of
the reaction and some characteristics of the resulting
N-Vinylpyrrolidone of chemically pure grade was
dried with potassium hydroxide and distilled in a vac-
uum. For polymerization we used the fraction with
bp 65oC at a pressure of 200 Pa, n
was synthesized by the procedure described in .
The purity was monitored by the elemental analysis,
determination of the content of double bonds, and
Found (%): C 47.25, H 6.11, S 15.41, C=C 11.80.
Calculated (%): C 47.06, H 5.88, S 15.69, C=C 11.76.
Chemical shifts d (ppm) and multiplicity of signals
for the indicated atoms are presented below.
109.5 153.0 20.4 164.5
70.3 28.3 48.5 55.8