ISSN 1070-4272, Russian Journal of Applied Chemistry, 2014, Vol. 87, No. 4, pp. 474−479. © Pleiades Publishing, Ltd., 2014.
Original Russian Text © A.V. Pestov, I.S. Puzyrev, A.V. Mekhaev, T.I. Gorbunova, V.I. Saloutin, S.V. Smirnov, D.I. Vichuzhanin, P.P. Matafonov, 2014, published
in Zhurnal Prikladnoi Khimii, 2014, Vol. 87, No. 4, pp. 482−487.
AND POLYMERIC MATERIALS
Modiﬁ cation of Adhesive Materials Based on Epoxy Oligomers
with Fluorinated Organic Compounds
A. V. Pestov
, I. S. Puzyrev
, A. V. Mekhaev
, T. I. Gorbunova
, V. I. Saloutin
, S. V. Smirnov
D. I. Vichuzhanin
, and P. P. Matafonov
Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences,
ul. S. Kovalevskoi 22, Yekaterinburg, 620137 Russia
Institute of Engineering Science, Ural Branch, Russian Academy of Sciences,
skaya 34, Yekaterinburg, 620949 Russia
Received April 24, 2014
Abstract—N-Containing perﬂ uoropentanoic acid derivatives were used as modifying additives to commercial
epoxy resins. As shown by differential thermal analysis, the ﬂ uorinated organic derivatives exhibit catalytic
activity in curing of epoxy resins. The following characteristics of the adhesive compounds in the cured state
were determined: degree of swelling, gel fraction content, ultimate shear strength of the adhesive joint, adhesion
to low-carbon St.3 steel and AMg-6 aluminum–magnesium alloy, and corrosion-protective properties with respect
to these materials.
Modiﬁ cation of epoxy oligomers with inorganic [1–4]
or organic [5–8] compounds is an advantageous pathway
of the development of promising adhesive materials, as
it does not require preparation of new epoxy oligomers
[9, 10] and involves the use of commercially available
products. The role of organic compounds in chemical
modiﬁ cation of epoxy oligomers consists, as a rule, in
using their potential as curing agents for epoxy oligomers.
Organic compounds are effective modiﬁ ers of epoxy
resins, enhancing the service properties of adhesive and
paint-and-varnish compounds. Their use allows enhance-
ment of the heat and ﬂ ame resistance [7, 11–15], electrical
[16–20] and mechanical [5, 8, 21–24] properties, adhesion
[25–28], and corrosion-protective properties [29–33].
It is known that introduction of ﬂ uoroalkyl substituents
into the monomer structure allows preparation of poly-
meric materials with a valuable set of properties: frost and
heat resistance, resistance to aggressive media and sol-
vents, and oleo- and hydrophobicity [34–36]. Apparently,
incorporation of a ﬂ uorinated organic modiﬁ er into the
polymer network formed by curing of epoxy oligomers
will also impart additional positive properties to the new
materials . The necessary condition of modiﬁ cation of
commercial epoxy oligomers with ﬂ uorinated substances
is the compatibility of the base materials and curing agent.
Partially ﬂ uorinated compounds are commonly used for
these purposes [37–39].
The known mechanism of curing of an epoxy resin
with polyethylenepolyamines (PEPAs) [40, 41] suggests
the possibility of using such reaction centers as tertiary
amino group or quaternary ammonium. Under certain
conditions, both functional groups will act as Lewis bases
in reaction with the epoxy ring of the base oligomers.
The most readily available agents for this purpose are
perﬂ uorocarboxylic acid amides and their quaternary
ammonium salts (F-QASs).
There are only a few examples in the literature illus-
trating the approach in which the curing agent simultane-
ously imparts new useful properties to the epoxy resin
[7, 8, 24]. Thus study further develops the methodology
of ﬁ lling of epoxy resins with organic compounds, in
particular, with ﬂ uorinated organic compounds, with
the aim to prepare new high-performance adhesive and