Lesson

1 Chemicals found in Dyes

LEARNING COMPETENCY: Describe
the composition, properties and uses
What’s In of chemicals found in dyes, insect
repellants and their impact on the
environment
In the previous module, you
were able to discover the chemistry behind soap and detergent. You studied the
differences between soap and detergent regarding chemical compositions,
production, properties, and cleaning performance. You also learned about the power
of surfactant and builders to support the function of the two most commonly used
cleaning products.

To check the extent of your understanding of soap and detergent, answer the
simple activity below. Write a FACT if the statement is correct, and write BLUFF if
the statement is incorrect.

1. Soap and detergent have the same chemical composition.

2. Soap is not effective on hard water because it forms scum or film.
3. Detergents are made up of natural raw material.
4. Surfactants reduce water hardness.
5. Detergent thick foam is mostly non-biodegradable.

If you got all the answers to this quick review, you are now ready for the next
lesson. In this module, you will learn the chemistry behind dyes and insect
repellants. You will study the different chemical compositions found on common
insect repellants and their possible environmental effects.

What’s New

According to the article by artTECA,

people are exposed to color psychology as soon
as they are born. For example, baby girls’
dresses are commonly in pink while boys are in
blue. Colors also reflect the deeper character of
a person than simply following a specific fashion
trend. Colors have the power to reveal one’s
feelings, emotions, identity, and taste in fashion.
A Canadian study found out that 90% of
consumers’ first impressions of clothes are
Photo Source:
https://www.bluemagnetinteractive.com/blog/color- based on color alone. There are also times when
psychology-boosting-web-conversion/
your dressing choices influence what others
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think of you and influence what you think of yourself. For instance, a black suit
shows authority and power while others wear a red dress to captivate people and to
show energy and strength. These are why the textile industries continuously try to
improve their technology on coloring fabric through time.

Direction: Answer the following questions:

1. What color of clothes do you usually wear? Why do you like those colors?
2. What is the importance of color to fabrics and textiles?
3. In Color Psychology, colors have a different meaning. Choose 3 colors and
identify the moods, feelings, or meanings related to them according to your
interpretation.

What is It

Dyes are organic compounds that are widely used for imparting color to
textiles. They are produced either from natural or synthetic resources. Unlike paint
(pigments), they do not build upon the material’s surface but are absorbed in the
fibers’ pores. It is possible because of the following reasons:

a. The dye molecules are smaller than the size of the pores of the fibers. The
planar shape of its molecules with a little thickness helps to slip into the
fiber’s polymer system.
b. There is an affinity between the dye and the fiber due to the force of
attraction.

The Unique Properties of Dyes

Unlike most organic compounds, dyes possess color due to the following
reasons: (If one of these features is lacking, the color will be lost.)

a. Dyes absorb light in the visible spectrum (400-700 nm)

Wavelength of Light Absorption and the Colors in Organic Dyes

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 b. They have at least one chromophore (color-bearing group)

Examples of Chromophores Present in Dyes

c. They have a conjugated system – a structure with alternating double and

single bonds.

Examples of Conjugated System of Vitamin A and β-carotene

d. They exhibit resonance of electrons, the stabilizing force in organic

compounds.

A Resonance Structure of Malachite Green

The chromophore must be a part of the conjugated system. Just like the
figure below:
1. The first example shows a colorless compound because the
chromophore – the azo group is attached in between two methyl
group (not conjugated system)
2. The second example obtained an orange color because the
chromophore – the azo group is attached between two benzene rings
(a conjugates system)

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Auxochromes (color helpers)
● Can shift the color of the dye
● Attach the dyes to the fibers
● Most often used to influence the dye solubility
● Examples: carboxylic acid, sulfonic acid, amino (NH2), and hydroxyl (OH)
groups

Bathochromic shift (redshift)

● The position shift of a peak or signal to a longer wavelength (lower energy)
● Increases absorption and intensity (darker) of the color

Hypsochromic shift (blue shift)

● The position shift of a peak or signal to a shorter wavelength (high energy)
● Decreases absorption and intensity of the color

Factors that can intensify the color of the Dye

a. Doubling the length of the conjugated system causes a bathochromic effect.
b. Adding groups of electron-donating (auxochromes) has a bathochromic
effect.
c. Electron-donating (NH2) and electron-accepting (NO2) provide a
bathochromic effect.
d. Increasing the number of electron-attracting groups (chromophores)
conjugated with electron-donor (auxochromes) has a bathochromic effect.
e. The electron-donating effect of an amino group is enhanced by adding alkyl
groups to the N- atom.

EFFECTS OF SUBSTITUENTS TO THE INTENSITY OF AZO-DYE SYSTEM

Different Types of Dyes

There are things needed to consider in the development of dyes. A specific
type of dye can only absorb in a specific type of substrate or textile. A dye should
also have a greater affinity to the substrate (a type of fabric) than its medium
(acid, base, water). Different dyes also have a degree of permanence under the end -
use application, like stability to fading upon exposure to water (water fast) and/or
sunlight (lightfast). Therefore, you should know the different types of dyes and
their properties

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Natural Dyes
● Are obtained from natural sources like vegetable matter, mineral, insects or
are manufactured in the factory from petrochemical feedstock
Examples:

o Mauveine – first synthetic dye made from coal tar

o Indigo – brilliant blue color made from fermented leaves of a plant
o Red Lac dye – extracted from lac, a resinous protective secretion of a
tiny insect
o Iron oxide – gives a brown color
o Buff – derived from ferrous sulfate
Synthetic Dyes
● Acid Dyes (Anionic Dyes)
o Suitable substrates: polyamides like nylon
and proteins like wool, silk, and leather
o Acid dyes carry a negative charge (anionic) are
used to polyamides and proteins that carry a
positive charge (cationic) during the dyeing
process
o Applied in acidic conditions
o Inexpensive, lightfast but not wet fast
Example: Acid Black 1

● Basic Dyes (Cationic Dyes)

o Suitable substrates: polyacrylics
o Basic dyes carry a positive charge (cationic) are
used to polyacrylics that carry a negative
charge (anionic) during the dyeing process
o The basic dyes derived their name from the fact
that they possess a cationic group
o Good fastness and bright shades
Example: Mauveine (first synthetic dye), Basic Red 18

● Disperse Dyes
o Suitable substrates: Hydrophobic substrates
like polyesters and acetate
o Involve dissolving the dye in a polymer matrix
to form a solid-solid solution
o They are dispersed in water rather than fully
dissolved to carry out the dyeing process
o Since polyesters are hydrophobic and have
crystalline content, high temperature, pressure,
and carrier assistance lead to satisfactory
dyeing.
Example: Disperse Blue 165

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Dyes for Cellulosic Polymers

● Direct Dyes
o Suitable substrates: cellulosic polymers like
cotton, viscose rayon, and vegetable fibers
o Water-soluble and applied in the absence of a
binding agent, mordant
o Water-soluble and low fastness
o Gain proximity to the cellulose chain to
maximize the effects of intermolecular
interactions such as H- bonding
o Cheap, easy to apply but low fastness quality
o Add sodium chloride to accelerate absorption rate, sodium
bicarbonate to warm colors, and copper sulfate to cool colors
Example: Benzidine-based direct dyes

● Vat Dyes and Sulfur Dyes

o Suitable substrates: cotton, linen, rayon
o Used to enhance wet fastness of cellulosic
substrates (prevent color removal upon
water exposure
o Water-insoluble dye, but made soluble by
the use of sodium hydrosulfite dissolved in
a sodium hydroxide
o Vat dyes: Name derived from the vatting process during application
o Sulfur dyes: Name derived from the essential use of sulfur in their
synthesis
o Expensive and also called hot water dyes

Example: Vat dye - Natural dye indigo (dye for denim fabric)

● Azoic Dyes (Naphthol dye)

o Suitable substrates: cotton and nylon
o The color development takes place in a
coupling reaction between naphthol and diazo
component
o Wet fast but low lightfast
o Bright and high-intensity colors
o Also called cold water dyes
Example: Tie-dye (Fast dye or jobus)

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 ● Reactive Dyes
o Suitable substrates: natural and synthetic
cellulosic fibers
o Undergo chemical reaction with cellulose to
form a covalent bond
o Excellent and bright wet-fast shades on
cellulosic fibers
Example: Reactive Blue 19

What’s More

Activity1

Choose five items from the given scientific terms about dyes below. Then,
provide definitions of each based on what you have previously learned.

Visible Spectrum Conjugated system

Auxochrome Chromophore
Resonance of electrons Bathochromic shift
Hypsochromic shift Auxochrome

TERMS DEFINITION
1.
2.
3.
4.
5.

Assessment 1
Direction: Answer the following questions:

1. What is the difference between dye and pigment?

2. Why is it vital for a chromophore to be a part of a conjugated system in a
dye?
3. What is color intensity? What is the importance of this in dyeing a fabric?
4. How can you intensify the color of a dye?

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Activity 2

Complete the table below with information about the different types of dyes.

TYPES OF SUITABLE MEDIUM/

FASTNESS EXAMPLE
DYES SUBSTRATE SOLVENT
Poor light and Mauveine
Natural Not stated Water wet fast Red Lac dye
Buff
Synthetic
1) Light fast but
Acid Dye Acid Acid Black 1
not wet fast
2) 3)
Basic Dye Good fastness Basic Red 18
4) Disperse Blue
Disperse Dye Water Good fastness
165
5) Cellulosic 6)
Water Poor fastness
polymers
Vat and Sulfur Cotton, linen, 7) Natural dye
Wet fast
Dye rayon Indigo
8) Wet fast but 9)
Cotton, nylon Water
poor light fast
Cellulosic 10) Reactive Blue
Reactive Dye Water
fibers 19

Assessment 2

Direction: Answer the following questions:

1. What are the differences between natural and synthetic dyes?

2. Why is it important to choose a specific dye to a particular substrate or
fabric/textile type?
3. What does dye fastness mean? What is wet fast? What is light fast?
4. Which do you think is more environment-friendly? Is it natural or synthetic
dyes? Why?

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 What I Have Learned

To test whether you learned something from this module, answer briefly the
following questions below:

1. What is the difference between dye and pigment?

2. What are the benefits of using dye?
3. What makes dye unique compared to other organic compounds?
4. Choose one type of dye. Explain its composition, properties, and fastness.
5. What are the pieces of advice or tips you can give in choosing and using
perfect dye in a particular fabric?

What I Can Do

What is Tie-Dye?
It is a method of producing textile patterns by tying parts of the fabric to
shield it from the dye.

Procedures:

1. Prepare the following materials:

● Soda ash or washing soda (if available) - It will serve as
dye fixer.
● Azoic dye or fast dye (locally known as jobus) – Colors
of your choice
● White shirt (Best result can be attained if you will use
100% cotton) Note: If a white shirt is not available,
you may use a white handkerchief as an alternative.
● Rubber bands
● Strainer or rack for the dyeing process
● Plastic Bin to catch the dye
● A squirt bottle or Nozzle container
● Water

2. Cover your workplace with newspaper to protect it from

spills. It is also advisable for you to wear rubber gloves in doing
the tie-dye shirt.

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3. Prepare the shirt.
✔ It is best if your shirt is freshly laundered to make sure it is free from dirt,
soils, and other stains. This is to prepare the shirt for dyeing absorption.
Tie-dying is best done on damp fabric.
✔ If you have soda ash available, soak the shirt for about one to two hours
before applying the dye. Use one cup of soda ash for one gallon of warm
water. It allows the garment to have brilliant color and improve its
fastness.
4. Tie the shirt.
✔ This will give your tie-dye shirt the design. Lay your
shirt flat on a table or any surface.
✔ Example: Spiral Tie-dye pattern – You can use a
pencil, fork, or your thumb and index finger on this
step. Put it in the middle of the shirt or wherever
you want to have the design, and then twist it
continuously until the folds in the shirt form a circle.
✔ Use rubber bands to hold the design in place. The number of bands will
depend on you depending on the pattern and colors that you want to apply
on your shirt.
5. Prepare the Dye.
✔ Put your azoic or fast dye in a squirt bottle or
nozzle container. One bottle per color that you
desire.
✔ Then, add warm water to the bottle to dissolve the
fast dye. The amount of water will depend on the
color you want to achieve, or you can also follow
the manufacturer’s instructions on the dye’s packaging.
6. Start Dyeing the Shirt.
✔ Put your tied shirt on a strainer or rack with a
basin below. This is to make sure that the shirt
will not become too drippy wet with dye.
✔ Start to apply the dyes in a pattern that you desire.
You can alternately put the dye color according to
your choice of design. Dye both sides of the tied
shirt.
7. Shirt dripping, drying, and washing
✔ Let the dye sit on the shirt for a maximum of 24
hours.
✔ Then, wash the tied shirt with running water.
✔ Remove the rubber band and then rewash it with
water.
✔ Let it dry.
✔ Proceed with regular washing with detergent.
Photo sources from abs-pointilisim, How
to Tie Dye Your Shirts @steemit.com

Your output will be graded using the rubric below.

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 Criteria Points
4 3 2 1
Planned The artwork The student The
carefully, shows that did the assignment
made the student assignment was turned
sketches, and applied the adequately, in, but
showed an principles yet shows a showed little
advanced of design lack of evidence of
awareness of while using planning and any
the elements one or more little evidence understandi
and elements that an ng of the
Elements &
principles of effectively. overall element and
Principles of
design. Student composition principle of
Design
Student went met was planned. art; No
above and expectation evidence of
beyond s. planning.
expectations. Student did
the
minimum of
work
required.

All aspects of With a little The student Below

the artwork more effort showed average
were in finishing average craftsmansh
considered techniques, craftsmanshi ip, lack of
and patiently the artwork p; adequate, pride in
completed. could be or not as finished
The finished outstanding good as the product.
product is a . Overall, student’s Showed little
result of the project previous evidence of
Craftsmanshi
careful, is clean and abilities, a bit effort and/or
p & Neatness meticulous without careless. lack of
planning. The major Minor defects understandi
craftsmanshi mistakes. may be ng. Includes
p is present. obvious
outstanding. defects,
Project is
pristine and
well kept.

Submitted Submitted Submitted Submitted

the finished the finished the finished the finished
product on product 1 product 2-3 product 4
the set day after days after the and more
deadline. the deadline. days after
Time
deadline. the deadline.
Management

Execution, The product The product The product The

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 Originality was was was partially products
and successfully successfully successfully was started,
Uniqueness executed executed executed with but never
from concept from a few unique fully
to concept to aspects. completed.
completion, completion. No unique
with a novel Unique and features and
and original original clear copy of
approach. with some other’s work.
evidence
from
samples.
All All One More than
requirements requiremen requirement one
Requirements
are met and ts are met. was not met requirement
exceeded. completely. was not met.
Points x 5 =

Assessment 2 Assessment 1
1. Natural from nature sources while synthetic a. Dye absorbs in fabric while pigment just
are chemical -based set above the surface of the material
2. For the dye to effectively absorb on fabric b. To produce color
with excellent fastness c. Color becomes darker or lighter.
3. Degree of permanence under end-use d. By adding chromophores, auxochromes
application; light fast if not fading in and conjugates system
exposure to sunlight; wet fast when exposed
to water
4. Natural dyes What’s More
Activity 1
Activity 2 Answers may vary.
a. Polyamides
b. Polyacrylics What’s New
c. Base
d. Hydrophobic substrates like polyesters Q1. Answers may vary.
and acetate Q2. Enhance design/marketable value clothes
e. Direct dye Q3. Answers may vary.
f. Benzidine-based
g. Water with sodium hydrosulfite in sodium
hydroxide What’s In
h. Azoic dye 1. Bluff
i. Fast dye or jobus 2. Fact
j. Excellent fastness 3. Bluff
4. Bluff
5. Fact

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