ISSN 1070-3632, Russian Journal of General Chemistry, 2014, Vol. 84, No. 6, pp. 1091–1094. © Pleiades Publishing, Ltd., 2014.
Original Russian Text © M.A. Paserb, I.N. Bakirova, 2014, published in Zhurnal Obshchei Khimii, 2014, Vol. 84, No. 6, pp. 908–911.
Oligoesters on the Basis of Hydroxyethylated Derivatives
of 4,4'-(Propan-2,2-diyl)diphenol
M. A. Paserb and I. N. Bakirova
Kazan National Research Uiversity of Technology, ul. K. Marksa 68, Kazan, Tatarstan, 420015 Russia
e-mail: paserbm@mail.ru
Received October 28, 2013
Abstract—Equilibrium melt polycondensation was used to synthesize a series of oligoethers containing end
hydroxy groups, starting with hydroxyethylated derivatives of 4,4'-(propan-2,2-diyl)diphenol and saturated
aliphatic dicarboxylic acids. The structure of the oligoethers was assigned, and their physicochemical
characteristics and thermal stability were determined.
Keywords: 4,4'-(propan-2,2-diyl)diphenol derivatives, aromatic oligoesters, physicochemical properties,
thermal stability
DOI: 10.1134/S1070363214060061
Synthesis of polyfunctional reactive oligomers is an
important task of modern macromolecular chemistry.
One of the lines of activities in this field relates to the
synthesis of oligoesters which can be further used as
starting materials for heat- and fire-resistant poly-
urethane materials. Phosphorus- and halogen-
containing oligoesters for production of fire-resistant
polyurethanes have been described in [1, 2]. However,
such polymers have a fairly low thermal stability. One
of the synthetic approaches to materials combining fire
resistance and a high thermal stability consists in the
introduction into the polymer chain of benzene rings,
using aromatic oligoesters as the starting materials.
Oligoesters on the basis of phthalic anhydride and
diethylene glycol have been prepared [3]. Probably,
the thermal stability of oligoesters can be further en-
hanced using monomers with coupled aromatic
moieties as the component, containing hydroxyl groups.
The choice of compounds I and II is motivated by
the fact that they contain two hydroxy groups capable
of reacting with carboxylic acids to form ester bonds.
The presence of benzene rings in monomers I and II
makes it possible to include fragments containing two
aromatic rings into the oligoester to be synthesized.
The introduction of such fragments into the oligoester
chain gives us grounds to expect that the polyurethane
on its basis will feature enhanced thermal stability.
Moreover, by varying the degree of hydroxyethylation
of diphenol one will be able to vary the flexibility of
oligoester units, which, in its turn, will open access to
polymers with varied degree of flexibility.
Aromatic oligoesters were synthesized by poly-
condensation of aliphatic dicarboxylic acids with ex-
cess of compounds I and II. As the dicarboxylic acids
we took adipic and sebacic acids, which have different
numbers of methylene units between the carboxy
groups. The temperature and time regimes of the syn-
thesis and the characteristics of aromatic oligoesters
are presented in the table.
In the present work we used hydroxy-ethylated 4,4'-
(
propan-2,2-diyl)diphenol derivatives I and II to
synthesize oligoesters (Scheme 1).
Scheme 1.
CH3
H
O
CH2 CH2
O
C
O
CH2 CH2 O n H
n
CH3
I, II
n = 1 (I), 3 (II).
1
091