Russian Journal of Applied Chemistry, 2012, Vol. 85, No. 8, pp. 1225−1231.
Pleiades Publishing, Ltd., 2012.
Original Russian Text © E.V. Fomina, L.P. Korovin, V.A. Fomin, 2012, published in Zhurnal Prikladnoi Khimii, 2012, Vol. 85, No. 8, pp. 1288−1294.
AND INDUSTRIAL ORGANIC CHEMISTRY
Conditions of Synthesis and Properties of Dimethacrylate
Derivatives Containing a Fragment
of a Dimerized Fatty Acid
E. V. Fomina, L. P. Korovin, and V. A. Fomin
Kargin Research Institute of Polymers, Dzerzhinsk, Nizhni Novgorod oblast, Russia
Received January 10, 2012
Abstract—A series of dimethacrylate esters of a dimerized fatty acid were prepared. The dependence of their
formation rate on the kind of the glycol used was examined. The correlation between the molecular-weight char-
acteristics of the esters and their synthesis conditions is discussed.
Recently there has been particular interest in products
based on a dimerized fatty acid (DFA) [1–4]. Thanks to
the high reactivity of DFA, it is possible to prepare a wide
range of products ﬁ nding use in diverse ﬁ elds of industry
[5–7]. The unique physicochemical properties and ser-
vice characteristics of DFA derivatives, determined by
the presence of bulky cycloaliphatic substituents in acid
residues, make their studies topical.
Another important factor making DFA attractive is its
production from renewable plant materials.
Previously [8–11] we reported on the synthesis of DFA
oligo- and (co)polyamides, which are base raw materi-
als for preparing hot-melt adhesives with high adhesion
As a continuation of studies in the ﬁ eld of synthesis
of DFA derivatives, it was interesting to introduce into
a molecule containing a bulky DFA fragment methacrylate
groups capable of subsequent polymerization in the
presence of free-radical initiators or under UV irradiation,
to obtain polymeric adhesives with internal plasticization.
Combination of properties of the DFA cycloaliphatic
substituent and high capability of methacrylates for
polymerization will expand the applications of DFA
derivatives as adhesives and binders in production of
various composite materials, anaerobic sealants, and
The goal of this study was to synthesize new DFA
dimethacrylate derivatives and to examine how their
properties depend on the starting reactants and on the
conditions of synthesis and isolation.
We used the following chemicals: Pripol-1013 dimer-
ized fatty acid (linoleic acid dimer containing no less than
97% main substance, CAS no. 61788-89-4); DFA dichlo-
ride (DFA DC) synthesized according to ; methacrylic
acid [MAA, TU (Technical Speciﬁ cation) 6-01-914–79];
freshly distilled glycols and their monoesters: ethylene
glycol [EG, GOST (State Standard) 19710–83], diethyl-
ene glycol (DEG, GOST 10136–77), triethylene glycol
(TEG, TU 6-01-5–88 with revisions 1, 2), butylene glycol
(BG, TU 64-5-105–86), ethylene glycol monomethac-
rylate (EGM, TU 6-01-1240–80), and propylene glycol
monomethacrylate [PGM, STP (Enterprise Standard)
70–2005, Research Institute of Polymers]; preliminar-
ily distilled toluene (GOST 5789–78) and triethylamine
(GOST 9966–88); hydroquinone (GOST 2549–60); p-
methoxyphenol (TU 6-09-1248–71); p-toluenesulfonic
acid (p-TSA, TU 6-09-3668–77); sodium hydroxide
(GOST 4328–77 with revisions 1, 2); sodium chloride
(GOST 4233–77); distilled water (GOST 6709–72); and
copper(I) chloride (GOST 4164–79).