Russian Journal of Applied Chemistry, 2013, Vol. 86, No. 9, pp. 1441−1446.
Pleiades Publishing, Ltd., 2013.
Original Russian Text © M.S. Fedoseev, D.M. Devyaterikov, G.V. Rybina, A.E. Meshechkina, 2013, published in Zhurnal Prikladnoi Khimii, 2013, Vol. 86,
No. 9, pp. 1474−1479.
AND POLYMERIC MATERIALS
Curing of Oligo(Diene–Isoprene–Urethane–Epoxy)
Oligomer in the Presence of an Active Plasticizer,
1,2-Epoxycyclopentane, and of Its Adducts with Imidazoles
M. S. Fedoseev
, D. M. Devyaterikov
, G. V. Rybina
, and A. E. Meshechkina
Institute of Technical Chemistry, Ural Branch, Russian Academy of Sciences, Perm, Russia
Yaroslavl State Technical University, Yaroslavl, Russia
Received May 16, 2013
Abstract—Curing of a high-molecular-weight low-polarity oligo(diene–isoprene–urethane–epoxy) oligomer
PDI-3AK with methylendic anhydride and isophoronediamine in the presence of an active plasticizer, 1,2-epoxy-
cyclopentane, and of its adducts with imidazoles acting simultaneously as catalysts and plasticizers was studied
by differential scanning calorimetry in the dynamic mode. The glass transition points and physicomechanical
properties of the elastomers were determined.
Low-polarity high-molecular-weight oligo(diene–
isoprene–urethane–epoxy) oligomer PDI-3AK is used
for sealing of electrical items  and in adhesive  and
impregnation formulations . The oligomer curing is
mainly performed with diamines and acid anhydrides
via polyaddition to terminal epoxy groups. However,
poor physicomechanical characteristics of the polymers
obtained and high viscosity of the mixture do not meet the
modern technological requirements. Various plasticizers
are used for decreasing the viscosity: dibutyl phthalate,
dioctyl sebacate, and a mixture of derivatives of 1,3-di-
oxane alcohols and of their high-boiling ethers or esters
(EDOAs) [4, 5]. However, not all of these compounds
are effective. Many of them are poorly compatible with
PDI-3AK, deteriorate the physicomechanical properties,
and can undergo exudation in the course of storage, which
shortens the warranted service life of items.
Therefore, active efforts are made to ﬁ nd new plasti-
cizers that would be chemically and thermodynamically
compatible with PDI-3AK and would actively participate
in the formation of the polymer structure. Their incorpo-
ration into the polymer matrix in the course of oligomer
curing can fully exclude exudation in storage. One of
such active plasticizers is 1,2-epoxycyclopentane, which
is prepared by oxidation of cyclopentene, a hydrocarbon
recovered from the С
fraction of naphtha pyrolysis,
with an aqueous solution of hydrogen peroxide [6, 7].
An increase in the volume of pyrolysis production makes
topical the problem of utilization of pyrolysis products,
in particular, of cyclopentene.
Oxygen-containing alicyclic compounds such as
1,2-epoxycyclopentane, 1,2-cyclopentanediol, and cy-
clopentanone are used for preparing macromolecular
compounds, plasticizers, fragrances, pharmaceuticals,
bactericidal agents, and agricultural chemicals.
Alicyclic epoxides are used for preparing polymeric
materials based on epoxy and phenolic resins and exhibit-
ing high heat resistance, good insulating properties, and
enhanced mechanical strength.
In this study, we examined a new cyclic monomer,
1,2-epoxycyclopentane (ECP) , as an active plasticizer
and it adducts with imidazoles as catalysts of curing of
Curing of PDI-3AK in the presence of 1,2-epoxycy-
clopentane and its adducts with imidazoles was also per-
formed with cyclic curing agents: methylendic anhydride
(MEA) and isophoronediamine (IPD).