Russian Journal of Applied Chemistry, 2011, Vol. 84, No. 9, pp. 1596−1599.
Pleiades Publishing, Ltd., 2011.
Original Russian Text © M.S. Fedoseev, V.A. Glushkov, L.F. Derzhavinskaya, G.F. Krainova, T.G. Tiunova, 2011, published in Zhurnal Prikladnoi Khimii,
2011, Vol. 84, No. 9, pp. 1547−1550.
AND POLYMERIC MATERIALS
Synthesis and Curing of Epoxy–Anhydride Polymers
Modiﬁ ed with an Oxirane
of the Tetrahydroquinoline Series
M. S. Fedoseev, V. A. Glushkov, L. F. Derzhavinskaya,
G. F. Krainova, and T. G. Tiunova
Institute of Technical Chemistry, Ural Branch, Russian Academy of Sciences, Perm, Russia
Received May 19, 2011
Abstract—Epoxy–anhydride polymers were prepared from diphenylolpropane diglycidyl ether and
isomethyltetrahydrophthalic anhydride in the presence of a chemical modiﬁ er, oxirane of the tetrahydroquinoline
series. The kinetics of the reaction of the modiﬁ er with the anhydride and the curing kinetics of the polymeric
compound containing the modiﬁ er were studied. The thermal properties and water absorption of the polymers
after their curing and structure formation were determined.
Thanks to a favorable combination of physicome-
chanical, adhesion, and insulation properties, polymeric
materials based on epoxy binders are widely used in
spacecraft engineering, in aircraft, machine, and ship
building, in radio electronics, in building, and in homes
. One of the drawbacks of many epoxy materials is
low water resistance. They absorb up to 8–10% water,
which impairs their heat resistance [2, 3].
One of possible ways to enhance the water resistance
of polymers is introduction into their structure of
hydrophobic chemical modiﬁ ers that do not cause phase
segregation of the system in the course of the synthesis,
do not give rise to thermodynamic and aggregative
instability of the system [4, 5], and do not deteriorate
the physicomechanical and thermal properties of the
material under the action of elevated temperatures
and strains. It was shown  that the water resistance
of epoxy–anhydride polymers is enhanced by their
modiﬁ cation with polyﬂ uoroalkyl glycidyl ethers in the
course of curing.
In this study we prepared epoxy–anhydride polymers
modiﬁ ed with an oxirane of the tetrahydroquinoline
series, containing ﬂ uorine atoms in the molecule, and
examined the properties of the products.
We used vinylimidazole produced by Alfa Aesar
(Lancaster). The melting point of the oxirane (OTQ)
was determined with a PTP device. Thin-layer
chromatography was performed with Sorbﬁ l silica gel
plates. The chromatograms were visualized under UV
light. The IR spectrum was recorded with a Bruker IFS
66ps Fourier spectrometer (mull in mineral oil); the
С NMR spectra, with a Varian Mercury+300
spectrometer (300 and 75 MHz), solvent CDCl
references HMDS and residual solvent signal (CHCl
C NMR, δ = 77.0 ppm); and the mass spectrum, with
an Agilent 6890N device equipped with an MSD 5975В
mass detector. Elemental analysis was performed with
a Leco CHNS 9321P device.
(OTQ, mixture of diastereomers) was synthesized
by epoxidation of the corresponding oleﬁ n with
m-chloroperoxybenzoic acid (MCPBA), following the