Organic Pigments for Industrial Applications

Coatings

Coatings

Decorative Industrial

Water Solvent Powder Metal

Automotive Industrial Marine
Based Based Coatings decorative

2
 Coatings Industry End User Mix in
Dollar terms
Aerospace Packaging
Protective and 2% 3%
Marine
13%

OEM Architectural
6% 43%

Refinish
7%

Industrial
26%

3
 Automotive Coatings

Automotive

•OEM
•Refinish

4
 Automotive Coatings-OEM

• Aesthetic Appeal
• Long term protection
• Long term color retention

Complex Resin systems

Metallic Shades
Transparent Pigments
Effects are very important
Guaranteed performance

5
 Automotive Coatings-
Refinish
• Aesthetic Appeal
• Short term protection
• Hiding of defects
• Short term color retention

Complex Resin systems

Metallic Shades
Transparent Pigments
Effects are very important
Lower Guaranteed
performance

6
 Qualification Process-OEM

• Selection process based on

– Color space Timeline ~ 2.5
years, minimum
– Florida durability
– Universal usage in solvent borne and
waterborne
– Physical properties
– Heat stability
– Bleeding < DE1
– Marking resistance

7
 Metal Coatings

• Used for Industrial applications

Coil •
•
Roofing;
White Goods
Coatings • Building Cladding

• Used for Food Packaging cans

Packaging •
•
Canning Industry
Metal Can exteriors
Coatings • Direct food contact metal interior

8
 Coil Coatings
Total coating thickness is
less than 30 microns

Baking temp – 280 deg 1

mins. Effective 180 deg for
30 mins

• Advantages
– Flexibility of the coating allows for
fabrication operations post
coatings( post formation)
– Long term exterior durability

9
 Packaging Coatings

10
 Packaging Coatings
Characteristics

Coatings add additional

functionality to the can

Add barrier and aesthetics

to the Can

Provide protection and cost

advantage to the metal

11
 Packaging Coatings

• Most of the coating resin is Epoxy

• Polyester for exterior
• Stoving alkyd for low end applications

• Sterilization stability
• Good weather fastness
• Compliance to FDA

12
 Powder Coatings

Powder Coatings are becoming popular

because of the 5 ‘E’s
– Excellence of finish
– Environmental friendliness
– Economics
– Energy saving characteristics
– Ease of application

•Resin systems
•Pure Epoxy
•Epoxy Polyester
•Acrylic( Mostly Europe)
•Polyurethanes
 General Industrial Coatings

• Major Purpose of these coatings

is to protect
– Stoving Enamels
– Floor Coatings
– Underground Pipe Coatings
– Ship Bottom Coatings
– Chemical protection coatings
– Anti corrosive primers
– Road Marking Paints

14
 General Industrial Coatings

• Resin systems
– Polyester
– Stoving Alkyds
– Epoxy
– Poly urethane
– Acrylic
– ….many more

15
 General Industrial Coatings

• Key Properties
– Aesthetics
– Protection
– Identification
– Functional

16
 General Organic Pigment
Manufacturing Process

NH 2 + NaNO2 + HCl

+
N N + OH N=N OH
Cl-
General Organic Pigment Mfg Process

Dryer
 Naphthol AS
• History

• Discovered by Schöpf in 1892

• Color ranges from yellowish to
very blue shade reds O H
O HO N OC2 H5
• Bleeding risk N
• Industrial and ink applications H2N N

Diazonium
+
Coupling component
Naphthol AS

Mono Azo Pigment

 Naphthol AS
• Pigment Red 170
• Hue
– Saturated mid shade red
– Opaque
O
– Transparent H
O HO N OC2 H5
• Borderline bleeding property
N
• Good chemical and heat H N N
2
resistance
• Darkening after exposure
 Benzimidazolone
• Pigment Orange 36

• Hue H3C
O 2N
– Orange N
N
O
H
• Unsaturated N H
O N
• Opaque O
• Excellent durability Diazonium N
H
• Pigment chemistry of choice
for lead free coatings
Benzimidazolone
 Benzimidazolone
• Pigment Yellow 151 / 154

• Hue
– Greenish / Reddish
• Opaque
• Excellent durability PY 151
• Poor alkali stability vis-vis PY
154
• Pigment chemistry of choice for
lead free coatings

PY 154
PY 151 v/s PY 154
 Quinacridones
History
– Chemical structure O H
discovered in 1935 by H.
Liebermann N
– Manufacturing processes
established in 1955
N
– 1958 first pigments
commercially available H O
– Standard pigment chemistry
for the Violet and Magenta
area in all application areas
 Quinacridone
• Pigment Violet 19

• Polymorphism: Different crystal

structures give different hues:

– alpha, not stable, leads to… O H

– beta, violet-blue N

– gamma, red-yellow
N
• Transparent & Opaque
H O
linear trans-Quinacridone
 Quinacridone
• Pigment Violet 19

• Polymorphism:
 Quinacridone
Pigment Red 122

• Hue: High saturated bluish red,

so called “Magenta”
• Highly transparent to semi CH3 O H
opaque grades available N CH3
• Rheology sensitive
• Excellent durability
N
• Used in all industry areas
H O

2,9- di-methyl Quinacridone

 Isoindolinone
• Pigment Yellow 109 / 110 Cl
Cl Cl
• Tetrachloroisoindolinone CH3 H
N O
• Hue Cl N N
– PY 109 green shade yellow
N Cl
– PY 110 red shade yellow O H Cl
• Durability Cl
Cl
– PY 109 good only at higher levels PY109
– PY 110 excellent in all areas
• No bleeding
Cl Cl
• Used in all industry areas
Cl Cl Cl Cl

Cl N N Cl
N N
O H H O

PY 110
 Isoindoline
Pigment Yellow 139

• Hue
– Red shade yellow O O
• Durability
HN NH
– Good weatherfastness N
– Darkens in masstone O H O
N N
• Good solvent and migration H O O H
resistance PY139
• Used in all industry areas
 Diketo – Pyrrolo- Pyrrole (DPP)
• History
• Discovered in the early 80s
• Last new chromophore with high
success in the HPP as well as in H R
the industrial / architectural area
O N
• Hue
– Deep bluish red, medium red to
orange
• High saturation O
• Opaque and transparent N
R H
• Excellent durability
 Diketo – Pyrrolo- Pyrrole (DPP)
• Pigment Red 254

• Hue H Cl
N
– Saturated medium O
red
• Opaque O
• Excellent durability
N
Cl H
 Diketo – Pyrrolo- Pyrrole (DPP)
• Pigment Red 264

• Hue
– Deep saturated H
O N
blue shade red
• Transparent
• Excellent durability
N O
H
 Indanthrone
• Pigment Blue 60
– Hue
• Very red shade
– High transparency
– Less saturation than PB15:1 Indanthrone
PB 60
– Excellent durability
O

O HN
NH O

O
 Anthraquinone
• Pigment Red 177
– Hue
• Blue shade red
– High transparency
– Acceptable durability

O NH2

O
O

Anthraquinone NH2 O
PR 177
 Dioxazines

Cl
N O N
C2H5
C2H5
N O N
Cl

PV 23
• Unique, very blue-shade red
• Very high color strength
• High chroma
• Bleed resistant
• Fair weatherfastness
• Used as a shading component for
blues
Metal Complex Pigments
 Phthalocyanine
R R
• History
• Beginning of the 19th century blue R R
substances discovered, but structure
only elucidated in 1933 by ICI R N N R
N
R R
• First pigments were commercialized
in 1935 by ICI N Cu N
R R
• Non-polar structure N N N
R R
• Flocculation
• Wetting behavior R R

R R

R = H, Cl, Br
 Phthalocyanine Blue
R R

• R = 0-8 Cl R R
• Different crystal structures give
different hues R R
N N
• alpha PB15, PB15:1, PB15:2 R
N
R
red shade blue N Cu N
• beta PB15:3, PB 15:4 R R
green shade blue (most stable form) R N N N R
• gamma PB 15:5
red shade blue R R
• epsilon PB 15:6
very red shade R R

R = H, Cl
 Phthalocyanine Green
Cl Cl
• Pigment Green 7 Cl Cl
Cl Cl
– R= 14-15 Cl N

– Hue Cl N N
• Blue shade green N Cu N
N N
– Good durability Cl Cl
N
– Used in all industries Cl
Cl Cl
Cl Cl
 Phthalocyanine Green
Br4-0 Br4-0

• Pigment Green 36 Cl0-4

Cl0-4
– R= 4-9 Br, 8-2 Cl N
– Hue N N
• Yellow shade green N Cu N
– Mainly used in coatings N N
N
Cl0-4 Cl0-4
Br4-0 Br4-0
 Thank You

41