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Dyes
Are substances that can be used to impart color to other materials,
such as textiles, foodstuffs, and paper. Unlike pigments, dyes are absorbed
to a certain extent by the material to which they are applied. The colors from
some dyes are more stable than others, however. A dye that does not fade
when the material it was applied to is exposed to conditions associated with
its intended use is called a fast dye. Contrariwise, a dye that loses its
coloring during proper usage is referred to as a fugitive dye. Some of the
conditions that could cause such a change in the properties of a dye include
exposure to acids, sunlight, or excessive heat as well as various washing and
cleaning procedures. Certain dyes may be considered both fast and fugitive,
depending on the material with which they are used.
The first man made organic dye, mauveine, was discovered by William
Henry Perkin in 1856. Many thousands of dyes have since been prepared
and because of vastly improved properties imparted upon the dyed materials
quickly replaced the traditional natural dyes. Dyes are now classified
according to how they are used in the dyeing process.
Acid dye - Water soluble anionic dyes that are applied to fibres such as
silk, wool, nylon and modified acrylic fibres from neutral to acid dyebaths.
Attachment to the fibre is attributed, at least partly, to salt formation
between anionic groups in the dyes and cationic groups in the fibre. Acid
dyes are not substantive to cellulosic fibres.
Basic dye - Water soluble cationic dyes that are applied to wool, silk,
cotton and modified acrylic fibres. Usually acetic acid is added to the
dyebath to help the take up of the dye onto the fibre. Basic dyes are also
used in the coloration of paper.
Mordant dye - As the name suggests these dyes require a mordant. This
improves the fastness of the dye on the fibre such as water, light and
perspiration fastness. The choice of mordant is very important as different
mordants can change the final colour significantly. Most natural dyes are
mordant dyes and there is therefore a large literature base describing dyeing
techniques.
Vat dye - These dyes are essentially insoluble in water and incapable of
dyeing fibres directly. However, reduction in alkaline liquor produces the
water soluble alkali metal salt of the dye. In this leuco form these dyes have
an affinity for the textile fibre. Subsequent oxidation reforms the original
insoluble dye.
One other class which describes the role dyes have rather than their mode of
use is food dyes. This is a special class of dyes of very high purity. They
include direct, mordant and vat dyes. Their use is strictly controlled by
legislation. Many are azo dyes but anthraquinone and triphenylmethane
compounds are used for colours such as green and blue. Some naturally
occurring dyes are also used.
Pigments:
Are the basis of all paints, and have been used for millennia.
They are ground colored material. Early pigments were simply as ground
earth or clay, and were made into paint with spit or fat. Modern pigments are
often sophisticated masterpieces of chemical engineering. In biology,
pigment is any color in plant or animal cells. Nearly all types of cells, such
as skin, eyes, fur and hair contain pigment. Creatures that have deficient
pigmentation are called albinos.
In the coloring of paint, ink, plastic, fabric and other material, a pigment is a
dry colorant, usually an insoluble powder. There are both natural and
synthetic pigments, both organic and inorganic ones. Pigments work by
selectively absorbing some parts of the visible spectrum (see light) whilst
reflecting others.
There are several kinds of chlorophyll, the most important being chlorophyll
"a". This is the molecule which makes photosynthesis possible, by passing
its energized electrons on to molecules which will manufacture sugars. All
plants, algae, and cyanobacteria which photosynthesize contain chlorophyll
"a". A second kind of chlorophyll is chlorophyll "b", which occurs only in
"green algae" and in the plants. A third form of chlorophyll which is
common is (not surprisingly) called chlorophyll "c", and is found only in the
photosynthetic members of the Chromista as well as the dinoflagellates. The
differences between the chlorophylls of these major groups was one of the
first clues that they were not as closely related as previously thought.
Carotenoids are usually red, orange, or yellow pigments, and include the
familiar compound carotene, which gives carrots their color. These
compounds are composed of two small six-carbon rings connected by a
"chain" of carbon atoms. As a result, they do not dissolve in water, and must
be attached to membranes within the cell. Carotenoids cannot transfer
sunlight energy directly to the photosynthetic pathway, but must pass their
absorbed energy to chlorophyll. For this reason, they are called accessory
pigments. One very visible accessory pigment is fucoxanthin the brown
pigment which colors kelps and other brown algae as well as the diatoms.
O N
H
SO2CH2CH2OSO3Na
Vinyl sulphone dye (Remazol Brilliant Blue R, C.I. Reactive Blue 19)
2. Monochloro-s-triazine dyes:
Cl
SO3Na N N
OH HN N N
N H
N
NaSO3 SO3Na
SO3Na N N N N NaSO3
OH HN N N N N NH OH
N H H N
N N
Nucleophilic addition:
H H
O - NaHSO O
4
DYE S C C OSO3Na DYE S CH CH2
O H H O
O H - O
- +Cellulose O +
DYE S CH C O Cellulose DYE S CH CH2
O H O
H2O
O H H
DYE S C C O Cellulose + OH-
O H H
• Semi-Continuous:
– eg. Pad - Batch
• Batchwise Exhaustion:
– eg. Winch, Jet, Package and Beam Dyeing
• Printing:
– eg. Print - Thermofix
“Usage”
Reactive dyes are used to dye cellulosic fibres. The dyes contain a reactive
group, either a haloheterocycle or an activated double bond, that, when
applied to a fibre in an alkaline dye bath, forms a chemical bond with an
hydroxyl group on the cellulosic fibre. Reactive dyeing is now the most
important method for the coloration of cellulosic fibres. Reactive dyes can
also be applied on wool and nylon; in the latter case they are applied under
weakly acidic conditions. Reactive dyes have a low utilization degree
compared to other types of dyestuff, since the functional group also bonds to
water, creating hydrolysis.
“Hot And Cold Dyeing Brands”
Cold reactive dyes are very reliable and used throughout the global clothing
and textile industries to permanently colour fabrics made from plant fibres.
The dyes react with the fibre on a molecular level to produce a permanent
bond that withstands wash after wash. The colour becomes part of the fabric.
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 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.
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.
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.
· hydrogen bonds
· dipole-dipole interactions
Disperse dyes have hydrogen atoms in their molecule, which are capable of
forming hydrogen bonds with oxygen and nitrogen atoms 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
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;
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".
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.
The temperature and chemical requirements for the dye reaction of fiber
reactive dyes, versus the dye deposition of disperse dye, are so different that
the idea of combining both in one step seems bizarre. Disperse dye is
applied at a boil, using a chemical to reduce the temperature needed for dye
transfer, while reactive dyes, unlike direct dyes, are generally applied at
considerably lower temperatures, and may actually degrade quickly when
boiled.