✓Both dyes and pigments fall under the umbrella

term of “colorants.”

✓Dyes and pigments are both used to color

materials, although the way in which the coloring
process takes place is different for each.
✓Dyes require some sort of physical or chemical reaction

in order for the dyeing process to occur.

✓Pigments themselves are actual particles of color.

✓Unlike dyes, the coloring process with pigments requires

a binding agent in which the pigment itself is suspended.

Pigments are organic or inorganic, colored, white or
black materials that are practically insoluble in the
medium in which they are dispersed. They are distinct
particles, which gives the medium their color and
opacity.

Dyes are soluble in the medium in which they are

dispersed. This means that there are no visible particles
and the transparency of the medium is unchanged.
✓Pigments are insoluble in, and essentially physically and
chemically unaffected by the vehicle or substrate in
which they are incorporated and remain unaffected by
the surface or media on which it is applied or dispersed.
✓The coloring process with pigments occurs when the
binding agent, in which the pigment is suspended,
attaches to the material being colored.
✓The binding agent works as a vehicle in which pigments
can achieve the coloring process.
✓Pigments are materials that change the color of
transmitted or reflected light due to wavelength
selective absorption.
✓When white light falls on a sample, the light may be
totally reflected, in which case the substance appears
white or
✓the light may be totally absorbed, in which case the
substance will appear black.
✓If only a portion of the light is absorbed and the balance
is reflected, the color of the sample is determined by the
reflected light, i.e. if violet is absorbed, the sample
appears yellow-green and if yellow is absorbed, the
sample appears blue.
✓The colors are described as complementary.
Uses of Pigments:
✓The most important role of pigment is providing color
on any surface or for any item.
✓Apart from this, there are many more functions of
pigments. Some of them include:

❑Providing resistance against corrosion

❑ For improving surface strength

❑ For improving durability and weathering properties

✓Pigments are used in the manufacture or inks, paints,
plastics or other polymeric materials.
✓Pigments retain a crystal or particulate structure
throughout the coloration process.
 Difference between Dyes & Pigments

DYES PIGMENTS
Dyes are either water Pigments are insoluble in
soluble or soluble in water as well as most other
another type of solvent. solvents.
“Dye-bath” is typically The coloring of materials
where the reactions of the with pigments takes place
dyeing process occurs. on “the surface” of the
product being colored.
 Difference between Dyes & Pigments

DYES PIGMENTS
Particle size of dyes are less Particle size of pigments are
than 1 µ. more than 1 µ.
Dyes are absorbed by the Pigments are adsorbed by the
fabric. fabric.
Dyes have more attraction Pigments have less attraction
towards fabric as compare towards fabric as compare to
to pigments. dyes.
 Classification of Pigments

✓Pigments are classified into organic and inorganic

pigments.
❑Organic pigments: based on carbon chains and carbon
rings. However, they can also contain metallic
(inorganic) elements.
❑Inorganic pigments: chemical compounds not based on
carbon, are usually metallic salts precipitated from
solutions.
 Difference between Organic & Inorganic Pigments

ORGANIC PIGMENTS INORGANIC PIGMENTS

Organic pigments are brighter Inorganic pigments are dark and
compare to inorganic pigments. lower brighter compare to organic
pigments.

Plants and plant products are the Inorganic pigments are made from
base from which organic chemical and artificial components
pigments are made. only.
Organic pigments are safe on Inorganic pigments come with
use. serious side effects and might be
unsafe for use.
 Difference between Organic & Inorganic Pigments

ORGANIC PIGMENTS INORGANIC PIGMENTS

Smaller particle size compared to Larger particle size compared to
inorganic pigment. organic pigment.

Not preferred for long lasting Preferred for long lasting products.
products.

Fading and exposure to sunlight Have resistance against fading and

or chemicals can take away the exposure to sunlight or chemicals.
bright colour of organic
pigments.
 Difference between Organic & Inorganic Pigments
ORGANIC PIGMENTS INORGANIC PIGMENTS
More varieties, wider spectrum Less variety, narrow spectrum

High tinting strength Low tinting strength

Excellent acid and alkali Medium to fine acid and alkali

resistance resistance
Medium to fine solvent Excellent solvent resistance
resistance
Non-toxic, low toxicity Some varieties of high toxicity
(lead, chromium, mercury, etc.)
Higher cost Lower cost
 Different Classes of Organic Pigments
It is possible to classify organic pigments in the following groups:
Low Grade Pigments:
(1) Lakes of acid or Anionic dyes:
✓ These pigments are precipitated from the solution of anionic dyes of
the type
D-X+: Where D- = dye molecule having anionic groups &
X+ = metal ion eg. Sodium atom
✓ The precipitation is done with salt of heavy metals such as calcium
(Ca) or Barium (Ba). Eg. Lithol Rubine BK
COO
HO

N
2+
N Ca
H3C
SO 3

Lithol Rubine BK

✓ These pigments have poor fastness property due to high sensitivity

to acids and alkalis.
✓They are resistant to solvents.
 Different Classes of Organic Pigments
Low Grade Pigments:
(2) Lakes of basic or Cationic dyes:
✓ These pigments are precipitated from the solution of cationic dyes
of the type
D+X-: Where D+ = dye molecule having cationic groups &
X- = negative ion eg. Chlorine atom or salt
✓ Eg. Pigment Violet - 3 +
(H 3C) 2N N(CH 3)2

–
Cl

Pigment violet - 3
N
H CH3

✓These pigments have superior fastness properties.

 Different Classes of Organic Pigments
Low Grade Pigments:
(3) Metal complexes:
✓ This group of pigments have excellent light fastness property but
other fastness properties are inferior.
✓ These are co-ordination or chelate compounds and require for their
formation dye molecules which contain oxygen or nitrogen atom to
donate electrons to the metal atom.
✓ Eg. Pigment Green - B
 Different Classes of Organic Pigments
Low Grade Pigments:
(4) Neutral, metal free compounds:
✓ This is a large group of pigments consisting of mono azo and bis azo
compounds with a few vat dyes.
✓ These are mostly dye molecule not containing solubilizing groups
such as –SO3H or –COOH.
✓ They provide full range of hues (colour/shade).
✓ These pigments have good fastness to acids and alkalis but have
poor fastness to solvent and plasticizers.
 Different Classes of Organic Pigments
Neutral metal free compounds:
Monoazo Pigments:

O
H3C NH2
+
H3C NH
NO 2 O
4-methyl-2-nitroaniline 3-oxo-N-phenylbutanamide

-HCl

H3C N N CH2 NH
O
NO 2

Hansa yellow G
 Different Classes of Organic Pigments
Neutral metal free compounds:
Bisazo Pigments:
O

H2N NH2 + H3C

2
O NH
Cl Cl
3,3'-dichloro[1,1'-biphenyl]-4,4'-diamine 3-oxo-N-phenylbutanamide

-2HCl

O
NH Cl
N H3C
HO N N OH
CH3 N
Cl COHN

Pigment Yellow - 12
 Different Classes of Organic Pigments
(5) Nitro dyes:

H3C O O O
N NO 2 NO 2

O N NH NH
N
NH
CH3
Cl Cl

Hansa yellow G Pigment chlorine GG

 Different Classes of Organic Pigments
Modern High Grade Pigments:
✓In 1935, Monastral Blue was marketed by ICI.
✓This was first pigment with high all around fastness properties.
✓Copper phthalocyanine is an excellent example of this class.
 Different Classes of Organic Pigments
Modern High Grade Pigments:

(1) Azo Pigments:

✓ These have been obtained by using more complex diazo and

coupling components and in some cases by forming metal
complexes.
✓These show excellent fastness properties.
✓Eg. Nickel Azo Yellow
 Different Classes of Organic Pigments
Modern High Grade Pigments:
Azo Pigments:
Cl OH

2 + 2 + NiCl 2

N OH
NH2
4-chloroaniline quinoline-2,4-diol

OH

Cl N N

N
O
Ni

N O

N N Cl

OH Nickel Azo Yellow

 Different Classes of Organic Pigments
Modern High Grade Pigments:
(2) Azo Methine Pigments:

✓ Copper complexes of 2,2’-dihydroxy azomethine dyes possess

excellent light and heat fastness.

Azomethine Pigments:

N CH N CH

Cu

OH HO X O O

(X = H or Cl)
 Different Classes of Organic Pigments
Modern High Grade Pigments:
(3) Azo Condensation Pigments:

✓ CIBA prepared these pigments by condensing two mono azo

pigments.
✓ Eg. Pigment Red - 344 and Pigment Orange - 31
✓ These pigments are used in mass colouration of polymers and
high grade lacquers for automobiles.
 Different Classes of Organic Pigments
Modern High Grade Pigments:
Azocondensation Pigments:
COCl
HO
Cl

N + H2N NH2
N
2
Cl

2-chlorobenzene-1,4-diamine
Cl

-2HCl Condensation

CONH HNOC
HO OH
Cl Cl Cl

N N
N N

Cl Cl
 Different Classes of Organic Pigments
Modern High Grade Pigments:
PIGMENT ORANGE-31/CHRAMOPTHAL ORANGE
Synthesis:
HO COOH
HO COOH
Cl Cl

(i) Diazotisation N
NH2
+ N
(ii) Coupling

2-chloroaniline

3-hydroxynaphthalene Azo compound

-2-carboxylic acid
 Different Classes of Organic Pigments
Modern High Grade Pigments:
PIGMENT ORANGE-31/CHRAMOPTHAL ORANGE
Synthesis:
HO COOH Cl HOOC OH
Cl Cl
N N
+ H2N NH2 +
N N

Cl

-2H 2O Condensation

Cl
HO OH
Cl COHN NHOC Cl
N N
N Cl N

Pigment Orange - 31
 Different Classes of Organic Pigments
Modern High Grade Pigments:
(4) Tetrachloro isoindolin-1-one Pigments:

✓ These pigments have a new chromophoric system.

✓ These are prepared by condensing phthalimide derivative with p-
phenylene diamine.
✓ By using other diamines a full range of shades from greenish
yellow to orange, red, brown are obtained.
✓ Their fastness properties are very good.
 Different Classes of Organic Pigments
Modern High Grade Pigments:
Tetrachloro iso - indoline - 1 - one Pigments:
Isoindoline-1-one
Cl Cl
Cl
Cl
+ H2N NH2
2 NH
Cl
benzene-1,4-diamine
Cl O

3,3,4,5,6,7-hexachloro-2,3-dihydro-1H-
isoindol-1-one

Cl Cl
Cl N N Cl

Cl NH HN Cl

Cl O O Cl
 Different Classes of Organic Pigments
Indolinone Pigments:
Cl Cl
Cl N R N Cl

Cl NH HN Cl

Cl O O Cl

Indolinone Pigments

O O

NH NH
N
O H O
N N
H O O H

Pigment yellow 139

 Different Classes of Organic Pigments
Modern High Grade Pigments:
(5) Perinone and perylene Pigments:
✓ The perinone pigments are derived from Naphthalene-1,4,5,8-
tetra carboxylic acid and o-phenylene diamine.

NH2 H2N
HOOC COOH
+ +
NH2 HOOC COOH H2N

benzene-1,2-diamine benzene-1,2-diamine
naphthalene-1,4,5,8-tetracarboxylic acid

N O O O

N N N N
+
O N N N

Perinone orange Perylene Pigment (Perinone red)

 Different Classes of Organic Pigments
Modern High Grade Pigments:
Perinone and perylene Pigments:

✓ The orange has superior fastness to light, heat and solvents while
the red is inferior by reason of solvent bleed and migration.
 Different Classes of Organic Pigments
Modern High Grade Pigments:
(6) Quinacridone Pigments:

✓ The colour of the pigment depends on the different crystal

modifications.
✓ γ-modification is red while β-modification is violet.
✓ The excellent fastness property may be due to H-bonding
between neighboring molecules.
 Different Classes of Organic Pigments
Modern High Grade Pigments:
Quinacridone Pigments:
H3C H3C Br

+ Br2
CH3 Br CH3
1,4-xylene 1,4-dibromo-2,5-dimethylbenzene

NH2 Oxidation

O
H
N 2 HOOC Br

-2HBr Br COOH
N
H
O 2,5-dibromobenzene-1,4-dicarboxylic acid
Pigment violet 19
 Different Classes of Organic Pigments
Modern High Grade Pigments:

Quinacridone Pigments:
O
NH2 H
HOOC Br N
H3PO4

2 + Br COOH
AlCl 3
HN

2,5-dibromobenzene-1,4- O
aniline
dicarboxylic acid
O

NH

N
H
O
Pigment Violet - 19
 Different Classes of Organic Pigments
Quinacridone Pigments: H
N CH3
O

O
H3C N
H
Pigment red 122

H
N Cl
O

O
Cl N
H
Pigment red 202
Cl

H
N
O

O
N
H
Pigment red 209
Cl
 Different Classes of Organic Pigments
Modern High Grade Pigments:
(7) Thioindigo Pigments:

✓ Many derivatives of thioindigo prepared but only those that

contain methyl or chloro groups (or both) have been found to be
useful as organic pigments.
✓ These pigments are characterised by their clear red and orange
colours.
✓ One example is Thioindigo bordeaux.
 Different Classes of Organic Pigments
Modern High Grade Pigments:

Thioindigo Pigments:

✓ It has light fastness comparable with Phthalocyanine pigments.

✓ If the positions of any of the four chloride atoms are altered or
one of the chlorine atom is removed or one more chlorine atom is
introduced, there occurs solvent bleeding in the products.
 Different Classes of Organic Pigments
Modern High Grade Pigments:
(8) Dioxazine Pigments: 1,4-Oxazine

✓ In 1952, Hoechst introduced Carbazol Dioxazine Violet.

✓ It has good light fastness.

✓ However, its fastness to solvents and plasticizers is inferior to
other pigments.
 Different Classes of Organic Pigments
Modern High Grade Pigments:
Dioxazine Pigments:
SO3Na
Cl C2H5
HO 3S N O N

N O N
H5C2 Cl
SO3Na
Direct blue 108
 Different Classes of Organic Pigments
Modern High Grade Pigments:
(9) Phthalocyanine Pigments:

Phthalocyanine

✓ The Phthalocyanine are very near to ideal pigment as they show

all around fastness and comparatively cheap.
✓ The blue and green phthalocyanine pigments have an excellent
fastness properties.
✓ It has been prepared from chelate metal.
✓ Eg. Copper phthalocyanine
 Different Classes of Organic Pigments
Modern High Grade Pigments:

Phthalocyanine Pigments:

CN CuCl
Cuprous chloride
4
180 - 300 C
CN 1 hr

benzene-1,2-dicarbonitrile

Copper phthalocyanine
 Different Classes of Organic Pigments
Modern High Grade Pigments:
(10) High Grade Anthraquinone Pigments:

✓ Several vat dyes are used as high grade anthraquinone pigments.

✓ Eg. Indanthrone, Flavanthrone, Halogeno dibenzanthrone,
Sulphonamide, Halogen-iso-dibenzanthrone etc.
 Different Classes of Organic Pigments
Modern High Grade Pigments:
High grade Anthraquinone Pigments:
O
Cl
NH
Cl
O O

NH
Cl
B. P. 984 110 (CIBA)
O
Cl O S N

O HN

O
N S

O
NH

O
B. P. 998 704 (BASF)
O
 Different Classes of Organic Pigments
Modern High Grade Pigments:
High grade Anthraquinone Pigments:
O

O HN
NH O

Indanthrone

O
O

N
Flavanthrone
Dyeing with Organic Pigments:

✓Organic pigments are dyes that are insoluble in water

and dissolve with great difficulty in organic solvents.
✓They can be applied as metal-free, neutral compounds,
as metal chelate complexes or as sparingly soluble salts
(Lakes).
✓Organic pigments are commercially available as
dispersion (pastes) or easily dispersible powders, tablets
or flakes.
Uses of Organic Pigments:

✓Surface coating agent.

✓In cosmetics, soap, wax, chalks, crayons, artist’s colours
and so on.
✓In printing and textiles in combination with a resin
(binder – a solid or liquid synthetic organic polymer).
✓Pigments are incorporated in cellulose pulp to obtain
coloured paper.
✓In mass colouration of synthetic fibres, plastics and
rubber.
Different areas of application of pigments
✓There are different kinds of pigment preparations for
both organic and inorganic variants.
✓These are used in different kinds of applications.
✓Some of the most important areas are as follows:

Printing inks – The printouts that we take from printers

also have colored pigments. Infect all kinds of printing inks
contain pigments in some form or the other.
Different areas of application of pigments
Paints – Pigment paste is quite commonly used in paints
of all varieties. Right from protective coating paints to
decorative coating paints, pigments are used in almost all
segments.

Textile and leather paints – Various kinds of paints are

used for garment printing and leather printing. Polyesters
and nylons absorb colours in the best manner and retain
the same for long period of time.
Different areas of application of pigments
✓Due to the presence of toxic heavy metals in some of the
inorganic compounds used as pigments, a number of
them have limited or entirely prohibited use.
✓For example, chromate pigments are rarely used, due to
environmental problems associated with chromium.
✓Similarly, cadmium compounds have been mostly
phased out to their high toxicity.
✓Clearly, this rules out a number of the pigments featured
in the graphic for use – hence the utility of organic
pigments!
✓Inorganic pigments originally derived from colored
minerals.
✓While inorganic pigments are still used in traditional
applications, such as paints, ceramics and cement, their
resistance to the effects of radiation, temperature and
chemical attack has also led to use in high technology
applications, such as fibers, engineering plastics and
even space equipment.
✓Inorganic pigment particles maintain their physical form,

unlike dyes that dissolve in the substrate that they color.

✓These particles are typically larger and more color stable

in different applications than organic pigments.

✓However, organic pigments tend to have higher strength

and often provide more vibrant colors.