Russian Journal of Applied Chemistry, 2013, Vol. 86, No. 10, pp. 1610−1616.
Pleiades Publishing, Ltd., 2013.
Original Russian Text © B.A. Mamedov, R.A. Akhmedova, S.S. Mashaeva, M.Sh. Gurbanov, A.M. Guliev, 2013, published in Zhurnal Prikladnoi Khimii, 2013,
Vol. 86, No. 10, pp. 1659−1665.
Synthesis of Polyfunctional Polyconjugated Oligomers
of 4-Aminophenol and Their Use in Obtaining
of Antistatic Composite Materials
B. A. Mamedov, R. A. Akhmedova, S. S. Mashaeva, M. Sh. Gurbanov, and A. M. Guliev
Institute of Polymer Materials, National Academy of Sciences of Azerbaijan, Sumgait, Azerbaijan
e-mail: email@example.com, firstname.lastname@example.org
Received October 18, 2013
Abstract—Polyconjugated oligomers containing aromatic links with hydroxyl and amino functional groups were
synthesized by oxidative polycondensation of 4-aminophenol. They exhibit solubility and fusibility, heat resis-
tant, paramagnetic and semiconductor properties, and also high reactivity in reactions characteristic for aromatic
hydroxyl groups. These oligomers were used as supplements to industrial polymers. Composite materials were
obtained including a rubber with high physico-mechanical, thermal, and electrical properties.
Various types of conductive or antistatic polymer
composite materials are widely used in various ﬁ elds of
technology and industry, where electrostatic charges are
required, which arise from friction and deformation .
The preparation of such polymer composite materials is
possible using electrically conductive ﬁ llers, since com-
mercially available large-tonnage polymers are inherently
insulators of electrical current. Metal powders, various
carbon blacks, and powdered graphite are commonly used
as such ﬁ llers [2 , 3]. However, polymeric compositions
produced using the metal powders do not possess the
necessary elastic properties and good compatibility of
the polymer matrix to metal particles that presumably
leads to a rapid breakdown of conductive structures dur-
ing operation of products . At the same time, the use
of conductive ﬁ llers of polymeric or oligomeric nature is
more expedient, since in addition to conductivity they im-
part to composite materials valuable physico-mechanical
properties due to good compatibility of the components.
It is known that aromatic polyfunctional aromatic
polyconjugated oligomers possess a set of speciﬁ c prop-
erties (thermal and radiation resistance, paramagnetism,
semiconducting, catalytic, stabilizung and antistatic activ-
ity), as well as solubility and high reactivity in various
chemical reactions [5–8] .
Thus, oligoaminophenols (OAP) were synthesized
in the study, which contain reactive phenolic hydroxyl
groups in each elementary link. The resulting compounds
were further used as additive to produce heat-resistant
conductive polymer compositions for special purposes.
In a three-necked 500 mL ﬂ ask equipped with mechan-
ical stirrer, reﬂ ux condenser, thermometer, and bubbler
54.5 g (0.5 mol) 4-aminophenol and 28.0 g (0.5 mol) of
KOH and 250 mL (13.9 mL) of water were charged, the
mixture was heated to 368–371 K and purged with puri-
ﬁ ed oxygen for 8 h. The reaction mixture was cooled to
room temperature and neutralized with 10% hydrochloric
acid. KCl formed and unreacted monomer were washed
with hot distilled water on a glass ﬁ lter, OAP was dried
in vacuo (13.3 Pa) at 393 K to a constant weight.
The kinetics of the oxidative polycondensation and
oxidation of OAP was examined by a volumetric method
by measuring the volume of oxygen absorbed by the reac-
tion mixture at its constant pressure of 98.066 kPa [9, 10].
IR spectra were recorded on a spectrophotometer IR
Specord M-80, the samples of an oligomer in the form
lms deposited on single crystal NaCl; UV spectra, in