Disperse Dye

Disperse dye is originally developed for the dyeing of cellulose acetate.

They are substantially water insoluble. The dyes are finely ground in the
presence of a dispersing agent then sold as a paste or spray dried and sold as
a powder. They can also be used to dye nylon, triacetate, polyester and
acrylic fibres. In some cases a dyeing temperature of 130 deg C is required
and a pressurized dyebath is used. The very fine particle size gives a large
surface area that aids dissolution to allow uptake by the fibre. The dyeing
rate can be significantly influenced by the choice of dispersing agent used
during the grinding.

Disperse dyes have low solubility in water, but they can interact with the
polyester chains by forming dispersed particles. Their main use is the dyeing
of polyesters, and they find minor use dyeing cellulose acetates and
polyamides. The general structure of disperse dyes is small, planar and non-
ionic, with attached polar functional groups like -NO2 and -CN. The shape
makes it easier for the dye to slide between the tightly-packed polymer
chains, and the polar groups improve the water solubility, improve the
dipolar bonding between dye and polymer and affect the colour of the dye.
However, their small size means that disperse dyes are quite volatile, and
tend to sublime out of the polymer at sufficiently high temperatures.

The dye is generally applied under pressure, at temperatures of about 130oC.

At this temperature, thermal agitation causes the polymer's structure to
become looser and less crystalline, opening gaps for the dye molecules to
enter. The interactions between dye and polymer are thought to be Van-der-
Waals and dipole forces.

The volatility of the dye can cause loss of colour density, and staining of
other materials at high temperatures. This can be counteracted by using
larger molecules or making the dye more polar (or both). This has a
drawback, however, in that this new larger, more polar molecule will need
more extreme forcing conditions to dye the polymer2.
The most important class is the azo class. This class of azo disperse dyes
may be further sub-divided into four groups, the most numerous of which is
the aminoazobenzene class. This class of dye can be altered as mentioned
before, to produce bathochromic shifts. A range of heterocyclic
aminoazobenzene dyes are also available. These give bright dyes, and are
bathochromically shifted to give blues. The third class of disperse dye is
based on heterocyclic coupling components, which produce bright yellow
dyes. The fourth class are disazo dyes. These tend to be quite simple in
structure. Other than these, there are disperse dyes of the carbonyl class, and
a few from the nitro and polymethine classes.

Common and Generic Names for Disperse Dyes

Colour Index Names for PROSperse Disperse Dyes

PRO chem # Name Colour Index Name

D118 Bright Yellow Disperse Yellow 218
D225 Clear Orange Disperse Orange 25
D333 Fuchsia Disperse Violet 33
D350 Flame Scarlet Disperse Red 325
D360 Bright Red Disperse Red 60
D426 Turquoise Disperse Blue 26
D450 National Blue Disperse Blue C-4RA (manufacturer's mix?)
D459 Bright Blue Disperse Blue 56
D460 Deep Navy Disperse Navy 35
D650 Cool Black Disperse Black C-MDA (manufacturer's mix?)
D770 Meadow In House Mix
D773 Sage In House Mix
D880 Iris In House Mix
D885 Lilac In House Mix
D125 Buttercup In House Mix
 APPLICATION OF DISPERSE DYES:

Dyeing Polyester with Disperse Dyes

Polyester requires the use of disperse dyes. Other types of dyes leave the
color of polyester almost entirely unchanged. While novices happily charge
into dyeing with acid dyes (for wool or nylon) and fiber reactive dyes (for
cotton and rayon), often with excellent results, the immersion dyeing of
polyester is a different story.
However, disperse dye can be used by even young children to make designs
on paper, which can then be transferred to polyester fabric, or other
synthetics, with a hot iron. The possibilities are endless, using fabric
crayons, rubber stamps, painting, and even screen printing.

Stamp Pad Ink

Disperse dye can be applied to paper with rubber stamps, and then ironed on
to polyester, just like the crayons. You can use special, large-scale fabric
stamps to apply other dyes to fabric, but only disperse dyes allow such fine
lines that almost any rubber stamp designed for use on paper will work, if
your fabric is smooth enough. Look for a product called "Heat Set Ink" at
companies that sell rubber stamping supplies. Caroline Dahl's wonderful
book Transforming Fabric gives source information for this material, in
addition to many project ideas and beautiful inspiring photographs of works
made with disperse dye on polyester.

PROPERTIES OF DISPERSE DYE:

Fastness to light is generally quite good, while fastness to washing is highly
dependent on the fibre. In particular, in polyamides and acrylics they are
used mostly for pastel shades because in dark shades they have limited
build-up properties and poor wash fastness.
Chemical characteristics and general application
conditions
Disperse dyes are characterised by the absence of solubilising groups and
low molecular weight. From a chemical point of view more than 50 % of
disperse dyes are simple azo compounds, about 25 % are anthraquinones and
the rest are methine, nitro and naphthoquinone dyes.

The dye-fibre affinity is the result of different types of interactions:

· hydrogen bonds

· dipole-dipole interactions

· Van der Waals forces.

Disperse dyes have hydrogen atoms in their molecule, which are capable of
forming hydrogen bonds with oxygen and nitrogen atoms on the fibre.

Dipole-dipole interactions result from the asymmetrical structure of the dye

molecules, which makes possible electrostatic interactions between dipoles
on the dye molecules and polarised bonds on the fibre.

Van der Waals forces take effect when the molecules of the fibre and
colourant are aligned and close to each other. These forces are very
important in polyester fibres because they can take effect between the
aromatic groups of the fibre and those of the colourant.

Disperse dyes are supplied as powder and liquid products. Powder dyes
contain 40 - 60 % of dispersing agents, while in liquid formulations the
content of these substances is in the range of 10 - 30 %. Formaldehyde
condensation products and ligninsulphonates are widely used for this
purpose.
Dyeing with disperse dyes may require the use of the following
chemicals and auxiliaries:
· dispersants: although all disperse dyes already have a high content of
dispersants, they are further added to the dyeing liquor and in the final
washing step

· carriers: for some fibres, dyeing with disperse dyes at temperatures below
100 °C requires the use of carriers. This is the case with polyester, which
needs the assistance of carriers to enable an even penetration of disperse
dyes below boiling temperature. Because of environmental problems
associated with the use of these substances, polyester is preferably dyed
under pressure at temperature >100 °C without carriers. However, carrier
dyeing is still important for polyester-wool blends, as wool must not be
submitted to wet treatment at temperatures significantly above 100 °C

· thickeners: polyacrylates or alginates are usually added to the dye liquor in

padding processes. Their function is to prevent migration of the dye liquor
on the surface during drying

· reducing agents (mainly sodium hydrosulphite): they are added in solution

with alkali in the final washing step.

Disperse dyes are widely used not only for dyeing, but also for printing
synthetic fibres.

Environmental issues:
The environmental properties of disperse dyes are assessed under the
following parameters

Parameters of Comments
concern
Bio-eliminability Owing to their low water-solubility, they are largely
eliminated by absorption on activated sludge in the
waste water treatment plant
Organic halogens Some disperse dyes can contain organic halogens, but
(AOX) they are not expected to be found in the effluent after
waste water treatment (because they are easily
eliminated by absorption on the activated sludge) (see
also Section 2.7.8.1)
Toxicology The following disperse dyes potentially have an
allergenic effect: Disperse Red 1, 11, 17, 15; Disperse
Blue 1, 3, 7, 26, 35, 102, 124;

Disperse Orange 1, 3, 76; Disperse Yellow 1, 9, 39, 49,

54, 64.
Heavy metals
Aromatic amines These dyes are still offered by some Far East dealers and
manufacturers [294, ETAD, 2001]
Unfixed colourant Level of fixation is in the range of 88 - 99 % for
continuous dyeing and 91 - 99 % for printing
Effluent Conventional dispersants (formaldehyde condensation
contamination by compounds, lignosulphonates, etc.) are poorly
additives in the dye biodegradable (<30 % according to [186, Ullmann's,
formulation 2000], ca. 15 % according to [18, VITO, 1998]). Some
dyes are formulated with more readily eliminable
dispersants (albeit not suitable for all formulations).
More information is reported in Section 4.6.3
 Classes of disperse dye:

Azo Disperse Dye:

The most important class of disperse dye is the azo class. This class of azo
disperse dyes may be further sub-divided into four groups, the most
numerous of which is the aminoazobenzene class. This class of dye can be
altered as mentioned before, to produce bathochromic shifts. A range of
heterocyclic aminoazobenzene dyes are also available. These give bright
dyes, and are bathochromically shifted to give blues. The third class of
disperse dye is based on heterocyclic coupling components, which produce
bright yellow dyes. The fourth class are disazo dyes. These tend to be quite
simple in structure. Other than these, there are disperse dyes of the carbonyl
class, and a few from the nitro and polymethine classes. Below is an
example of a disperse dye2
Anthraquinone Disperse Dye:
Anthraquinone disperse dyes lack the water-solubilizing groups of the acid dyes, but they
are adsorbed by hydrophobic fibres such as nylon or acetate rayon with the aid of soap or
other agents that keep the dye suspended in the application bath.

In the synthetic dye field, many hundreds of individual products are manufactured. Of
these, a small number become established as market leaders in their particular area of
utility. Factors influencing the attainment of this status by a particular dye include hue,
brightness, ease of manufacture, dyeing properties and fastness properties. One dye that
has reached this position for the production of blue shades on polyester fibers is CI
Disperse Blue 56 which has a simple anthraquinone structure and is easily applied giving
bright blue colorations of high fastness.

Dyes of the anthraquinone series are noted for their brilliance of hue, especially in the
blue region, and also for their excellent fastness properties, especially fastness to light.
Unfortunately, they have relatively low tinctorial strength compared with all other major
classes of dye and they are costly to manufacture. The replacement of anthraquinone dyes
by other chromophores, because of their low cost-effectiveness, has been described by
Renfrew (Rev.Prog.Coloration, 15, 1985, 15) as "a commercially attractive but
technically difficult objective for dye manufacturers".

Thiocyanomethyl substituted anthraquinone disperse dyes

The present invention relates to disperse dyestuffs of the anthraquinone series which
contain at least one group of formula --Y--CH2 (SCN) where Y is a mono- or binuclear
aryl group, which dyestuffs are useful for dyeing or printing textile substrates consisting
of or comprising synthetic or semi-synthetic, hydrophobic high molecular weight organic
materials.

Light fastness:
The photofading behaviors of anthraquinone disperse dyes on polylactide fabrics were
investigated. The fabrics which had been dyed with 13 commercial dyes were exposed to
a carbon arc light source. The polylactide fabrics dyed with Disperse Red 127 or Violet
26, which have phenoxy substituents, showed the light fastness higher than 4 grade.