Russian Journal of Applied Chemistry, 2009, Vol. 82, No. 7, pp. 1263−1267.
Pleiades Publishing, Ltd., 2009.
Original Russian Text
A.A. Mamutova, E.V. Balashov, 2009, published in Zhurnal Prikladnoi Khimii, 2009, Vol. 82, No. 7, pp. 1167−1171.
AND INDUSTRIAL ORGANIC CHEMISTRY
Synthesis and Modiﬁ cation of Sulfur Dyes
A. A. Mamutova and E. V. Balashov
Al-Farabi Kazakh National University, Almaty, Kazakhstan
Received August 18, 2008
Abstract—An integrated approach to sulfur utilization by synthesis of sulfur dyes derived from m- and
p-phenylenediamine was suggested. The sulfur dyes obtained were modiﬁ ed by the reaction with butyl bromide.
The possibility of dyeing cotton fabrics by the dyes prepared was examined, and the coloration fastness was
An important line of scientiﬁ c and technical progress is
the development of new processes ensuring protection of
the environment from pollution with industrial discharges
and wastes. Of particular importance is utilization of
sulfur from petroleum-extracting industry.
Vast world’s resources of sulfur, need for sulfur
utilization, and development of textile industry are
decisive factors stimulating production of sulfur dyes.
Sulfur dyes, which are the cheapest among synthetic
organic dyes, give fairly fast coloration, but the majority
of them have dull tints . The assortment of sulfur
dyes is restricted to black, blue, brown, olive green,
violet, green, and yellow colors. Red and ruby colors
are lacking. The dyeing power of sulfur dyes is poor,
which leads to large dye expenditure . On the other
hand, with respect to resistance to various factors (except
chlorine), sulfur dyes are among valuable products of
dye chemistry . They are used for dyeing cotton and
viscose staple ﬁ ber, yarns, fabrics, and tricot. Despite
the above-indicated drawbacks, interest in sulfur dyes in
the world has not disappeared. Sulfur Black is the ﬁ rst
black dye. Only the empirical formula of Sulfur Black
is known: C
. It is also
used in ball pen inks. Studies are made to reduce to
a minimum the content of insoluble particles in aqueous
inks, which tend to accumulate at the pen ball. To this
end, Sulfur Black dye before use is either oxidized with
hydrogen peroxide or treated with 6 M HCl.
Along with cotton dyeing, the possibility of Nylon-6,6
dyeing with various types of sulfur dyes using sugars was
examined. In this case, deeper tints were obtained than in
dyeing by traditional procedures [5, 6]. Silk dyeing with
sulfur dyes using Na
S for mordanting was examined.
The resulting coloration on various substrates shows high
More than 90% efﬁ ciency of the process is attained
in reduction of sulfur dyes with environmentally friendly
agents: isomaltose, trehalulose, fructose, and sucrose,
with the subsequent oxidation of the material .
A novel procedure was developed for dyeing with
reduced sulfur dyes at 5–120°C, followed by oxidation
in the presence of enzymes such as bilirubin oxidase,
catechol oxidase, laccase, polyphenol oxidase, and
ascorbate oxidase .
An ozone–air mixture is used for intensiﬁ cation of
the dyeing process and improvement of the parameters
of cotton fabric dyeing, with simultaneous treatment of
wash waters .
A protective system for sulfur-containing textile
dyes against oxidants, especially bleaching agents, has
been developed. A dyed fabric is washed with a solution
, and Gd
ions or their combinations
. Recently an interest in the synthesis of styryl sulfur
dyes has been observed [12, 13].
The phenothiazine moiety is the main structural
unit of many sulfur dyes prepared from aromatic
amines. Phenothazinyl-containing aromatic amines
themselves found use as amorphous molecular materials
for optoelectronics, exhibiting high heat resistance