project:

Vat dyes

By:
SALMAN ALOUDAH

Supervisor:
Prof/Dr. Hassan Ali Ali Etman

1
Table of Contents
Table of Contents ............................................................................................................................................................... 2

1. Introduction.................................................................................................................................................................. 3

1.1 Functional Groups ................................................................................................................................................. 5

2. Literature Review: ....................................................................................................................................................... 5

2.1 Vat dye application ................................................................................................................................................ 6

2.2 Previous studies ...................................................................................................................................................... 7

2.3 Vat dyes properties ................................................................................................................................................ 9

2.4 Advantages of Vat Dyes .......................................................................................................................................11

3. Methodology:..............................................................................................................................................................12

3.1 Printing technique................................................................................................................................................12

3.2 Analyses and measurements ...............................................................................................................................13

3.3 Determination of antibacterial activity by measuring colony forming unit (CFU) .......................................13

3.4 Colour strength (K/S value) and fastness properties measurements ..............................................................13

3.5 Testing of dye effluent .........................................................................................................................................13

3.6 Analyses of the quality of dyed fabrics ..............................................................................................................14

3.7 Dye effluent analysis ............................................................................................................................................15

4. Result...........................................................................................................................................................................16

5. Conclusion ..................................................................................................................................................................17

6. References ...................................................................................................................................................................17

Table of tables:
Table 1: shows the commercial names and chemical structures of carbocyclic vat dyes. ................................................. 4
Table 2 : Heterocyclic commercial names and chemical structures of vat dyes .............................................................. 4

Table of figures:
Fig 1: The dyeing reactions of vat dye functional groups. ................................................................................................. 6

2
1. Introduction

Dyeing is the process of adding colour to a textile material using a dye (colour). Flowers,
nuts, berries, and other types of vegetables and plants, as well as animal and mineral sources,
are used to make dyes. These are referred to as natural dyes. Synthetic dyes are the other
type of dye. These are based on specific chemical compositions. Acid (anionic) dyes, basic
(cationic) dyes, neutral pre metalized dyes, sulphur dyes, vat dyes, reactive dyes, and
pigment dyes are some of these dyes. Colour is applied to fabric using various dyeing
methods for different types of fibre and at various stages of the textile production process.[1]

With the exception of concentrated sulfuric acid, vat dyes are compounds that are practically
insoluble in water and other solvents. The dye molecules contain chromophoric groups that
promote the colour of the compound (usually carbonyl groups involved in a conjugated bond
system) and auxochromic groups that can change both the absorption wave-length and
intensity.[2]

Because of their low substantivity towards synthetic fabrics and the generally pale shades
that result from their limited diffusion within synthetic fabrics, cotton, vat dyes are not
commonly used on synthetic fabrics.[3]

3
Table 1: shows the commercial names and chemical structures of carbocyclic vat dyes.

Table 2 : Heterocyclic commercial names and chemical structures of vat dyes

4
1.1 Functional Groups

All vat dyes share a chemical property in their insoluble pigmentary form. They are all made
up of one or more pairs of carbon atoms that are doubly bonded to an oxygen atom. These
carbon atoms are always part of a condensed system of benzene or other aromatic ring
structures with a closed system of alternating double and single bonds between adjacent
carbon atoms (which looks like chicken wire when drawn). [4]

The sodium salt of the leuco-vat dye is fully ionised in strongly alkaline solutions (pH 12-
15), yielding a negatively charged dye anion with associated positively charged sodium
cations. Under acidic conditions, this may be converted to the insoluble or sparingly soluble
vat-acid form of the vat dye, vat pigments are dissolved, or the nature and purpose of the
aftertreatment of vat dyeings with chemicals, necessitates at least a rudimentary
understanding of what the terms reducing agents, reduction, potential, oxidising agents,
oxidation, and oxidation potential mean. Redox systems are chemical systems that include
both reduction and oxidation reactions.[5]

2. Literature Review:

Vat dyes are a well-known dyestuff for producing brilliant hues in a variety of colour ranges.

Other useful dyes for camouflage textiles are vat dyes. The most visible colours for
camouflage patterns based on natural objects are olive green, brown, khaki, and black. CIE
colour parameters and spectral reflection properties in the visible and near-infrared spectrum
ranges can be used to measure target colours.[6]

5
The nature and purpose of the aftertreatment of vat dyeings with chemicals, or how vat
pigments are dissolved, necessitates a basic understanding of the terms reducing agents,
reduction, potential, oxidising agents, oxidation, and oxidation potential. Redox systems are
chemical systems that include both reduction and oxidation reactions.[7]

Fig 1: The dyeing reactions of vat dye functional groups.

2.1 Vat dye application

Vat dyes and their derivatives are promising organic electronics materials, with applications
including organic light-emitting diodes, liquid crystal screens, field-effect transistors, and
solar cells. Composite electrodes such as Vat Green 8/graphene, Vat Brown BR/graphene,
and Vat Olive T/graphene have also been shown to improve the specific capacity of Li-ion
batteries (LIBs).[8]

Wearable electronics and smart on-skin biosensors may play an important role in the
advancement of preventive and personalised medicine by enabling continuous monitoring of
human health conditions and controlled drug delivery.Electronics that come into direct
contact with the human body must be both safe and biocompatible. As a result, the organic
semiconductor materials used should be low toxicity and charge stable.[9]

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transport properties and excellent tolerance to mechanical stress ambient atmosphere
conditions. From this vantage point, vat dyes, which are frequently referred to as "green
materials," appear to be prospective semiconductor materials capable of meeting all of the
aforementioned requirements while remaining inexpensive due to mass production.[10]

The dye application method consists of three stages: alkaline reduction and dissolution of the
vat dye (typically using sodium hydroxide and sodium dithionite (hydrosulphite)), absorption
of the substantive leuco compound by the fibre aided by electrolyte (e.g. sodium sulphate
and wetting, dispersing, and levelling agent), and regeneration of the vat dye inside the fibre
via oxidation in air or hydrogen peroxide. To obtain the final colour, the dyed fibre is
thoroughly washed (washed with soap or special detergent at a high temperature) to remove
any surface dye and complete any dye aggregation inside the fibre.[11]

A biocompatible organic electronic device based on PEDOT:PSS has been demonstrated for
the delivery of neurotransmitters in nervous system treatment. Perylendiimides and their
derivatives are another class of compounds with well-studied toxicity profiles, suggesting
their suitability for biosensing applications. The biocompatibility of fullerene C60 and
pentacene, two common organic semiconductors, was investigated.

Cathodic reduction of vat dyes with the addition of a mediator (a soluble reversible redox
system, such as an iron [II/III]-amino complex) has the potential to reduce chemical costs
and chemical load in waste water by 50-75%.

2.2 Previous studies

Extensive study has been conducted on military textile camouflage." It has been discovered
that the optimal reflection spectrums of the colours brown, green, and black are 25%, 40%-
50%, and 10%, respectively.[12]

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Furthermore, vat dyes are highly resistant to washing, sunlight, and chlorine bleaching on
cotton, linen, rayon, and cellulose acetate fabrics.

However, the use of sodium dithionite to reduce vat dye endangers the environment and
eventually raises the cost of wastewater treatment. In recent years, low-impact biotechnology
has introduced new types of treatment in the reduction process of vat dyes with natural
reducers. [13]

Previous studies investigated that vat dyes have several important advantages, including low
toxicity, stability in air/moisture conditions, low cost, and availability in bulk quantities,
making them very appealing for further research. In this paper, we present a systematic
comparison of five vat dyes as semiconductor materials for use in wearable and on-body
electronics. A systematic variation of the dielectric nents enabled us to identify appropriate
material combinations that resulted in good electrical characteristics of OFETs. The data
analysis revealed some correlations between the surface energy of dielectric thin films and
the charge-carrier mobility values achieved in OFET devices.[14, 15]

To gain a market share, several researchers attempted to dye PET fabrics with vat dyes or
indigo. Sugawara investigated vapour phase dyeing on PET fabrics, which necessitates
extremely high temperatures of up to 220-250 °C. Other authors proposed a leuco vat acid
dyeing method in which organic acids were added to the dyeing bath to reduce the pH to less
than 7. However, this dyeing method required the addition of organic acids, which raised the
cost of wastewater treatment. Only a few studies demonstrated that PA, PET, and other
synthetic fibres could be dyed with specific vat dyes using the standard (sodium
hydrosulphite/ sodium hydroxide) reduction system.[16]

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2.3 Vat dyes properties

When compared to the toxic fullerene and pentacene, some vat dyes, such as Vat Blue 20
and Vat Orange 9, have good biocompatibility profiles in contact with human tissue.
Antimicrobial properties are known to exist in some vat dyes.

Vat dyes are insoluble in water when oxidised, but dissolve in water when reduced. As a
result, they can be precipitated on the fibre surface via a series of reduction and oxidation
reactions. Furthermore, due to the presence of anthraquinone units, vat dyes such as
Indanthrenes are thermally stable. Because of their excellent resistance to acid, alkali, and
bleaching, vat dyes were used to dye 40-50% of all cellulosics in the 1960s. Vat dyeing is
still used today for textile products that must withstand harsh conditions.[17]

Cotton can be successfully dyed with a variety of natural and synthetic dyes, including
direct, reactive, sulphur, vat, and azoic dyes. The dye chosen is determined by the desired
shade and its fastness.[18]

Vat dyes continue to account for a sizable portion of the dyestuff market in the coloration of
cellulose fibers/cotton; approximately 120,000 tonnes of vat dyes are used annually in the
global market. They have excellent all-around colour fastness, including washing, light,
perspiration, chlorine bleaching, and rubbing fastness, among other desirable properties for
cotton garments. They are also the only dye class that does not undergo significant shade
changes during the application of topical, cellulose reactive, flame retardant finishes. Vat
dyestuffs have a slight advantage over reactive dyestuffs in terms of environmental costs,
fewer CO2 molecules, lower water and energy consumption, and the ability to reuse treated
effluent, which has a decolorisation efficiency of more than 99%.[19]

The process of dying, to obtain solutions containing individual molecules or molecular ions,
vat dyes must be converted into a water soluble form (leuco form) by reducing agents in

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alkaline medium. Hydrose is the most commonly used reducing agent in vat dyeing.
Unfortunately, is being chastised for producing non-environmental decomposition products
such as sulphite, sulphate, thiosulphate, and toxic sulphur.[20]

Water-insoluble vat dyes are first converted into water-soluble leuco dyes by reduction with
a strong reducing agent, typically sodium dithionate. The vat dye exhibits substantivity
towards cellulosic fabrics in its reduced form and, after absorption, is re-oxidized to the
original water-insoluble form (in situ) in the fabric.[21] Whereas sodium dithionate is
commonly used to reduce vat dyes, it produces hazardous byproducts such as sulphite,
sulphate, thiosulphate, and toxic sulphur during the vat dyeing process. Many studies have
been conducted to replace sodium dithionite with more environmentally friendly alternatives.
Following on from this, some work was done with a hydroxyketone that meets the
requirements of the vat dye reduction process in terms of reductive efficiency and
biodegradability. However, due to the formation of strong smelling condensation products in
an alkaline solution, this compound is expensive and its use is limited to closed systems. [22]

Other sulphur-containing compounds used to reduce vat dye include hydroxyalkyl sulphinate
and thiourea. Furthermore, these compounds have a low sulphur content and equivalent
mass, which results in lower sulphur-based salt in wastewater. However, because Fe(OH)2 is
a strong reducing agent in alkaline medium, the possibility of using it for reducing organic
dyestuffs has been investigated. With increasing pH, the reducing effect of Fe(OH)2
accelerates. However, while vat dyeing occurs in alkaline medium, Fe(OH)2 is fairly soluble
in an alkaline solution and has a tendency to precipitate. As a result, it must be complexed in
order to remain in solution.[23]

Many studies see electrochemical reduction of vat dyes as an alternative route for
environmental reasons. Electrochemical reduction can be accomplished either directly or
indirectly. Direct electrochemical reduction replaces reducing agents with electrons from an

10
electric current, and effluent contaminating substances can be eliminated entirely. Although
this technique is ideal, the stability of reduced dye species is poor, which has an impact on
the technique.[24,25]

Among the dye classes used to colour cotton, vat dye is the most common. They account for
24% of the cellulose fibre dyestuff market in terms of value, and their application on
nanofibers has yet to be investigated. [26]

2.4 Advantages of Vat Dyes

Vat dyes are highly resistant to fading, making them ideal for use in textiles that will be
exposed to sunlight or frequent washing.

High wash fastness: Because vat dyes form strong chemical bonds with the fibres, they are
.highly resistant to washing. This ensures that the colour is retained even after several washes

Light resistance: Because vat dyes are highly light resistant, the colours do not fade even
.after prolonged exposure to sunlight.

Chemical resistance: Vat dyes are also resistant to chemicals like bleach, which can cause
.colour fading in other types of dyes.

Vat dyes are available in a variety of colours, ranging from bright and vibrant shades to
.more muted tones [27]

2.5 Disadvantages of Vat Dyes

The dyeing process for vat dyes is more complex and time-consuming than for other types of
dyes. It entails a number of steps, such as reduction, oxidation, and washing, which can be
labor-intensive and raise production costs.

Concerns about the environment: The production of vat dyes necessitates the use of harsh
chemicals and solvents that can be harmful to the environment if not properly managed. If
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waste generated during the dyeing process is not properly treated and disposed of, it can
.become a source of pollution

Chemicals used in vat dye production can be hazardous to workers' health, especially if
they are not properly trained and outfitted with protective gear. Skin irritation, respiratory
problems, and other health problems can result from exposure to these chemicals.

High cost: Due to the complex dyeing process and chemicals used in their production,
VAT dyes are generally more expensive than other types of dyes. This may limit their use in
certain markets and make them less accessible to small-scale textile manufacturers [28]

3. Methodology:

3.1 Printing technique

The aforementioned four fabrics, cotton, polyester, cotton/polyester 50/50, and

cotton/polyester 35/65, were printed using the flat silk screen printing technique. After
.printing and drying, the printed fabrics were steamed for 10 minutes at 100-102°C

The washing procedure

The washing procedure was as follows:

Following fixation, all printed samples were washed to remove excess material from the
fabric surface and to ensure the printed material's stability, as follows:

.Cold water was used to rinse the samples

.Hot water should be used to rinse the samples

Soap samples were treated for 15 minutes at 60°C with a solution containing 2 g/L
(TERGITOLTM NP-9 Surfactant) (non-ionic detergent). Wash samples in hot water first,
.then in cold water

.The washed samples are allowed to dry at room temperature

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Finally, fabrics were evaluated for colour strength (K/S), fastness properties, antibacterial
.properties, UV protection, and other factors [29]

3.2 Analyses and measurements

The colour strength of printed samples is measured as K/S and overall fastness properties
(washing, rubbing, and perspiration) according to standard methods after finishing the
treatment of the fabrics with conventional heat method and ultrasonic method and printing
them with the previously specified dyes.[30]

3.3 Determination of antibacterial activity by measuring colony forming unit (CFU)

Using the forming method (CFU), the antibacterial properties of treated textiles with
chitosan and chitosan nanoparticles against Staphylococcus aureus and Escherichia coli were
investigated. The number of active bacteria on the agar plate was counted under treated and
untreated conditions, and bacteria decrease was calculated using the equation R (%) = B-A/B
x 100. Where A is the CFU/ml of the treated sample after 16 hours of incubation and B is the
CFU/ml of the untreated sample after the same time period.[31]

3.4 Colour strength (K/S value) and fastness properties measurements

The colour strength (K/S) of the samples was determined using a Shimadzu UV/Visible
spectrophotometer and the light reflectance method. K/S, where K and S are absorption and
scattering coefficients, respectively. The printed samples were subjected to rubbing,
washing, sweating, and light exposure.[32]

3.5 Testing of dye effluent

The effluent was tested for TDS (total dissolved solids), TSS (total suspended solids), EC
(electrical conductivity), and pH after the dyeing process to determine the amount of these

13
compounds present in the effluent. Because large amounts of these compounds have a
negative impact on the environment. The effluent was diluted at a concentration of 0.5% for
this purpose, and the results were compared to standard results.[33]

Fast fashion has changed the perception of clothing from a valuable, long-lasting product to
a disposable, short-term item.

Cotton is considered a renewable resource, but its environmental impact is equal to or even
greater than that of polyester. Cotton recycling, on the other hand, can cut its carbon
footprint in half by reducing further cotton cultivation.[34]

3.6 Analyses of the quality of dyed fabrics

Shade characteristics (K/S value, colour difference, and uniformity): Colour eye-3100
Spectrophotometer was used to determine the color/shade strength K/S Value, colour
difference, and shade uniformity at 600 nm for Bezathren Blue RS and 480 nm for Bezathren
Red LGG vat dye. The vat dyed samples were folded four times and exposed to two times
(front and back) after calibration of the Colour eye-3100 Spectrophotometer using reducing
agents such as ferrous sulphate and hydrose combination and conventional reducing agent
(hydrose).[35]

Colour fastness: The colour fastness to washing can be tested using the ISO-2 test in a
launder-o-meter under the following conditions. A 10 x 4 cm swatch of the dyed fabric is cut
and stitched between two adjacent fabrics. The sample and adjacent fabric were washed for
45 minutes with 5g/l soap in a solution with a liquor ratio of 50:1 at 50°C. Following the
soaping treatment, the specimen is removed and rinsed twice in cold water, followed by a
rinse in cold running tap water. At 60°C, it was squeezed and dried. Colour fastness can be
tested using the AATCC Test Method-8-2005 and a Crock metre. The staining on cotton
rubbed fabric can be evaluated using a staining grey scale.[36]

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AATCC Test Method 16-2004 can be used to determine colour fastness to light. Colour
fastness to light is determined using a Carbon Arc or Xenon Arc Lamp source. The rate of
fading of eight AATCC blue-dyed wool standard samples is used to calculate the light
fastness system. To determine the colour change, the samples were exposed for 10 hours.[37]

Tensile strength: The dyed fabrics were tested for strength in both the warp and weft
directions using a universal Strength Tester.

ASTM D5034 random sampling method yielded a size of 100 mm x 150 mm.

3.7 Dye effluent analysis

The pH, total dissolved solids, BOD, and COD were all important parameters to consider in
this study. The vat dyed bath effluent was used to test the effluent parameters. Following
dyeing, the dye effluents were evaluated or analysed. Each stage's effluent was collected and
equalised to create a model effluent composition. The samples were collected in
polyethylene bottles. [37]

Over the last few decades, various strategies for converting cotton waste garments into new
value-added products have been developed. They are primarily classified as chemical and
mechanical approaches. Cotton waste is shredded, opened, and carded in the latter to recover
single cotton fibres. These can be pretreated or bleached before being spun into new yarns,
depending on their final application. However, strategies for preserving and reusing the
original colour are urgently needed to avoid the generation of additional effluents from
dyeing, such as wastewater. [38]

Furthermore, the textile colouring industry is currently concerned about economic and
environmental issues. As a result, it is always preferable to drain as few dyes as possible
from effluent. As a result, ensuring maximum dye uptake in a short period of time would
address these issues. In this regard, Vat dye, an anthraquinone-based water insoluble dye

15
with a coplanar and multi-ring system, is an ideal potential dye stuff capable of successfully
overcoming the major issues associated with reactive dyes. The chemical structure of the
reduced vat dyes facilitates dye molecule diffusion into the substrate surface. The dye
molecules are oxidised after being adsorbed on the substrate by Vander Waals forces and
diffused in the substrate to permanently trap them in the fibre polymer matrix. When
compared to reactive dyes, this permanent retention of dye molecules within the substrate
provides excellent fastness properties. Furthermore, vat dyes have long been used
commercially to dye various cellulosic fibres due to their wide shade range, excellent
reproducibility, and exceptional fastness properties.[39]

4. Result

Because of their more planar structure, vat dyes have a high affinity for cellulosic fibres and
provide the best fastness properties. These dyes are water-insoluble and cannot be used
directly on fabrics. To adhere to fibre, vat dyes require a vatting process that involves the
conversion of water-insoluble dyes into water-soluble leuco form. During the vatting
process, reducing agents such as sodium hydrosulfite and sodium hydroxide reduce the
carbonyl group. Finally, the absorbed water-soluble dye reverts to its original insoluble form
via oxidation with air or other oxidising regents, providing the dyed fabric with excellent
washing fastness (S).

Because vat dyes are insoluble in water, they are typically converted to soluble leuco states
by using sodium hydrosulphite (hydros) as a reductant in the presence of hydrated oxide
(NaOH), i.e. in an alkaline reducing solution.

Vat dyes are extremely washable and lightweight fast.

Vat dyes are more expensive than other types of dyes.

They are commercially available in a variety of forms, including powder fine.

16
5. Conclusion

In conclusion, we successfully developed a strategy for successful uniform dyeing of lyocell

fabric with vat dyes using a conventional high temperature dyeing technique. Three
commercial vat dyes were used to examine the dyeing behaviour of lyocell fabric in various
shades.[40]

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