organic pigments – the basics - sii - dec 2008
TRANSCRIPT
Public
ASEAN Regional Technical ServicTim Boyce
Organic Pigments –The Basics
(revised October 2008)
Slide 2
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
Principles of Principles of ColourColour
Types of Inorganic PigmentsTypes of Inorganic Pigments
Properties of Organic PigmentsProperties of Organic Pigments
Types of Organic PigmentsTypes of Organic Pigments
Clariant Product RangeClariant Product Range
Quality AspectsQuality Aspects
Synthesis of Synthesis of AzoAzo PigmentsPigments
Global Pigment MarketGlobal Pigment Market
Product SafetyProduct Safety
Agenda
Definition of Definition of ColourantsColourants
Public
ASEAN Regional Technical ServicCorporate Presentation
Global Pigment Market
Slide 4
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
Phthalo-cyanine
23%
Chromium3%
Iron oxide13%
Complex metal oxide
13%
Azo28%
Other inorganic
6%
High Per-formance
14%
Organic Pigments ~ 65% by value azo pigmentsphthalocyanine pigmentspolycyclics
Inorganic Pigments ~ 35% by value Iron oxidesComplex metal oxidesChrome pigmentsOthers * excluding titanium dioxide/fillers
Global PigmentMarket
Total Pigment Market (Value)(total market 2006 : ~ € 7.5 billion)
Slide 5
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
Organic Pigment Market by Application(total market 2006 : ~ 260,000 T)
Printing Inks56%
NIP1%
Coatings23%
Plastics15%
Special Applications
5%
Printing Inks35%
Coatings33%
Plastics19%
Special Applications
13%
By volumeTotal : ~ 260,000 T
By valueTotal : ~ € 5 billion
Global PigmentMarket
Slide 6
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Organic Pigments -The Basics
Tim Boyce
DIARYLIDE-YELLOW 22
LAKE RED 7
LITHOLRUBINE 12
OTHER LAKED 7
PHTHALOCYANINE 28
OTHER POLYCYCLIC 2QUINACRIDONE 2
SPECIAL AZO 4
NAPHTOL AS 4
TOL.RED / ß-NAPHTOL 4
PYRAZOLONE 2HANSA-YELLOW 3
REFLEX-BLUE 3
DIARYLIDE-YELLOW 18
LAKE RED 3
LITHOLRUBINE 7
OTHER LAKED 5
PHTHALOCYANINE 27OTHER POLYCYCLIC 8
QUINACRIDONE 8
SPECIAL AZO 9
NAPHTOL AS 5
TOL.RED / ß-NAPHTOL 2PYRAZOLONE 2
HANSA-YELLOW 3REFLEX-BLUE 3
Total Market 2006 : ~ 5.0 bn€
Total Market 2006: 260,000 T
Organic Pigment Market by Pigment Types
Global PigmentMarket
Slide 7
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Organic Pigments -The Basics
Tim Boyce
ROW8 %
Asia28 %
Americas34 %
Europe30 %
Organic Pigment Market (Value) by Region
(total market 2006 : ~ € 5.0 billionT)
Global PigmentMarket
Public
ASEAN Regional Technical ServicCorporate Presentation
The Principles of Colour
Slide 9
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
1. What is light?- Factorizing of light- Additive/subtractive mixing of colors
2. Interaction of light and matter
3. The creation of color- Color perception- Metamerism
4. The CIE-Color system- The CIE La*b*-System- Color differences
Principles of Colour
Slide 10
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
1. What is light?- Factorizing of light- Additive/subtractive mixing of colors
2. Interaction of light and matter
3. The creation of color- Color perception- Metamerism
4. The CIE-Color system- The CIE La*b*-System- Color differences
Principles of Colour
Public
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Organic Pigments -The Basics
To see objects we need lightTo see objects we need light.
Of the entire spectrum of waves in the universe, mancan visually perceive only a small wavelength range (400 - 700 nm), which we call light.
Rays with long wavelengths and extremely short wavelengths are invisible to the human being.
Light beam
Colour of light
Absorbing medium
Reflected residual light produces sensation of colour
Illumination
Principles of Colour
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Organic Pigments -The Basics
Spectrum of the electromagnetic waves.Spectrum of the electromagnetic waves.(logarithmic scale)
ultr
avio
let
infr
ared
Radio wavesLight wavesX raysγ- rays
Frequency (Hz)
(► decreasing)
Wavelength (m)(► increasing)
1 Xe 1 nm 1 mm 1 km
1023 1021 1019 1017 1015 1013 1011 109 107 105
visi
ble
mm
W
cmW
dmW
UK
W
KW
MW
LW
10-7 10310110-110-310-510-13 10-11 10-9
400 nm 700 nm
Principles of Colour
Slide 13
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Tim Boyce
Newton’s Experiment (1666)
Light source
PRISM
White Light
VIOLET (400nm)INDIGOBLUEGREEN (540nm)YELLOWORANGERED (700nm)
400 nm - 770 nm WhiteWhite400 nm - 435 nm VioletViolet435 nm - 480 nm BlueBlue500 nm - 560 nm GreenGreen580 nm - 595 nm YellowYellow595 nm - 605 nm OrangeOrange605 nm - 770 nm RedRed
350 nm - 400 nm Ultraviolet> 770 nm Infrared
visible
invisible
1 nm = 10 -9 m
Principles of Colour
Slide 14
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Tim Boyce
blue magenta
whiteyellow
Wavelengths mean colour
Principles of Colour
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Organic Pigments -The Basics
Additive Colour Mixing.In additive colour mixing, the single colours are added together to make white.This is only possible with light – not pigments or dyes.
Principles of Colour
Slide 16
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Tim Boyce
Example of additive mixing
yellow
green red+
The individual wavelengthsare “added” together
Principles of Colour
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Organic Pigments -The Basics
Subtractive Colour Mixing.
yellow cyan magenta
incident light
Absorption and scattering
Principles of Colour
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Organic Pigments -The Basics
Example of Subtractive Colour Mixing
Example: yellow/Cyan greenExample: Yellow + Cyan = Green
0,2
0,4
0,6
0,8
1,0
nm380 440 520 600 680
Tran
smis
sion
greenyellowcyan +
Only the wavelengthscommon to both contributing colours are responsible for the final colour. The final colour will alwaysbe lower in intensity than the initial colours.
Principles of Colour
Slide 19
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Tim Boyce
blue redgreen
yellowmagentacyan
Subtractive primary colours
Additive primary colours
Primary colours
Principles of Colour
Slide 20
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Organic Pigments -The Basics
Tim Boyce
1. What is light?- Factorizing of light- Additive/subtractive mixing of colors
2. Interaction of light and matter
3. The creation of color- Color perception- Metamerism
4. The CIE-Color system- The CIE La*b*-System- Color differences
Slide 21
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absorption(structure)
Reflection(surface)
Interaction of light and matter
scattering(particles /
particle size)
transmission(surface)
When light hits a surface ….
Principles of Colour
Slide 22
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Scattering, absorption, transmission, reflection
Blue lighttransmitted
Some greenLight transmitted
Yellow absorbed Red absorbed
Some red lightscatteredPrinciples of Colour
Slide 23
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Organic Pigments -The Basics
Tim Boyce
1. What is light?- Factorizing of light- Additive/subtractive mixing of colors
2. Interaction of light and matter
3. The creation of color- Color perception- Metamerism
4. The CIE-Color system- The CIE La*b*-System- Color differences
Principles of Colour
Slide 24
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Tim Boyce
Apart from wavelengths and colour physics, some otheraspects can affect the colour perception
opacity
haze
Reflection (flop)
gloss
surface
Principles of Colour
Slide 25
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Tim Boyce
Standardized Illumination D 65, A and C
rela
tive
radi
atio
n in
tens
ity
The standard illumination Acorresponds to An incandescent (tungsten) light bulb (2800 K), also called evening color.
The standard illumination Chas a radiation distribution similar to the northern daylight and was fixed in 1931 using a 2 ° observer
The standard illumination D 65(daylight) corresponds to a black body radiation at 6500 K
In addition there are standard fluorescent illuminations (F11, discontinuous spectrum etc).
Illuminant C was defined in 1931 (CIE 2° standard observer)and illuminant D65 was extended in 1964 (CIE 10° observer).
Principles of Colour
Slide 26
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Tim Boyce
Depending on the illumination the colour impression changes
Principles of Colour
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Metamerism
red
dependent
metamerism - free
metamerism
Light source Viewing angleReflectance
independent
red
Metamerism free Metameric
Spectral Curve same different
Visual perception ofcolour match
same different under different lights
Principles of Colour
Slide 28
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DeceptionsPrinciples of Colour
Slide 29
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InducedInducedColourColour
yelloweryellowerbluerbluer
Principles of Colour
Slide 30
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Principles of Colour
Slide 31
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Tim Boyce
Principles of Colour
Slide 32
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Organic Pigments -The Basics
Tim Boyce
Principles of Colour
Slide 33
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Tim Boyce
Principles of Colour
Slide 34
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Organic Pigments -The Basics
Tim Boyce
Principles of Colour
Slide 35
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Organic Pigments -The Basics
Tim Boyce
Principles of Colour
Slide 36
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Tim Boyce
Principles of Colour
Slide 37
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Tim Boyce
…….. And one last piece of fun
Slide 38
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Tim Boyce
1. What is light?- Factorizing of light- Additive/subtractive mixing of colors
2. Interaction of light and matter
3. The creation of color- Color perception- Metamerism
4. The CIE-Color system- The CIE La*b*-System- Color differences
Principles of Colour
Slide 39
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Tim Boyce
Color impression and color measuring
incident light
Object
absorption, reflection, scattering
emitted light
Eyebright/darkblue, red, green
Brain
color perceptionhues (max. 2 Mio)
Measuring Instrumentcolor intensityspectrum
Colorimetrics
Color description: CIE La*b*-SystemISO 7724-3, DIN 6174
Principles of Colour
Slide 40
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Tim Boyce
The Color Appearance
• Color of light of a light source goes direct to the eye.
• Color of light of a light source goes through a filter and then to the eye.
• Color of light of a light source hits the surface of a body and goes then to the eye.
Principles of Colour
Slide 41
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The human eye
The human eye has 2 different sensors for the detection of light. There are cone cells (3) and rod cells.
• There are 3 types of cones each for blue, red, green detection
• color impression, low light sensitivity
• vision during daytime
• The rod cells are for black & white detection, located in theouter part of the retina
• no color, high light sensitivity
• vision during night
rod cell
cell body
outer segmentsynaptic. region
cone cell
Principles of Colour
Slide 42
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Spectral sensitivity of the human eye
Red sensor
Blue sensor
Green sensorPrinciples of Colour
Slide 43
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THE EYE
RETINACORNEA
LENS
IRIS
LIGHT
PUPIL
LIGHT
Young EyesClear - Supple Lens
RETINA CORNEA
LENS
IRIS
LIGHT
PUPIL
LIGHT
Old Eyes Yellowing -Rigid Lens
Principles of Colour
Slide 44
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Color Vision DefectsMore than 200 million people worldwide have some color vision deficiencyOver 8% of males have this problem but only 0.5% of females
Different Races have different levels of deficiency and types ofdeficiencies
Colour deficiencies in males according to raceNorth America 8.00 %
Europe 8.76 %
Eastern Europe 9.31 %
China 6.15 %
Japan 4.50 %
Asia 6.00 %
Caucasian Population Males Females91.9 % 99.6 %
0.4 %
0.05 %
5.5 %
2.6 %
Normal trichromats
Anomalous trichromats
Dichromats
Principles of Colour
Slide 45
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We need:
1. Light2. Object3. Observer / Spectrophotometer + Software for
comparing the electric signal with the visual perception
incident ligh t
ob jectA bsorption , reflexion , scattering
em itted ligh t
E yebright/darkb lue, red , green
B ra incolour perceptionhues (m ax. 2 M io )
M easuring instrum entcolour in tensityspectrum
C olorim etrics
Color description: CIE La*b*-SystemISO 7724-3, DIN 6174
The human eye is represented by the color matching functions x, y and z
Color measurement
Principles of Colour
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0,1 0,2 0,5 0,60,40,3 0,70,0
0,8
0,9
0,1
0,2
0,5
0,6
0,4
0,3
0,7
xy - Diagram
The chromaticity diagram is a chart of all possible chromaticities in the axis based chart of colour coordinates.
To define the chromaticity only the values x and y are necessary.
CIE - Chromaticity Diagram
Spectral colour co-ordinates :
colour nm x y zRed Orange Yellow Green Blue Violet
670 620 585 525 470 400
0,74 0,69 0,54 0,08 0,12 0,18
0,26 0,31 0,46 0,84 0,07 0,00
0,00 0,00 0,00 0,08 0,81 0,82
The standard tristimulus colour values X, Y and Z are calculated into the standard chromaticity coordinates (x, y and z) as follows :
x = X(X+Y+Z)
y = Y(X+Y+Z)
z = Z(X+Y+Z)
Y is a dimension for the brightness of the colour.
Principles of Colour
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CIE Colour Model of 1931.
The three dimensional colour system defines coloursaccording to brightness and chroma, but does not show colours in the difference from each other in which they are perceived by the eye.
Later the CIE* XYZ Model (“shoe sole”) was developed from this.
Hue Lightness Chroma
*CIE = Commission International de l´Eclairage.
Principles of Colour
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CIE L*a*b* - Colour Model.
GreenGreen--a*a*
Black
WhiteL*
Red+a*
YellowYellow
+b*+b*
Blue-b* The CIE L*a*b* System was
introduced in1976. All modern measurement systems are based on it.
The colours are shown in their difference from one another as they are perceived by the eye.
Principles of Colour
Slide 49
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Colour measurement
greenish yellow
yellowish green
greenish blue reddish blue
reddish yellow
bluish redbluish green
yellowish red
CIElab - System DIN 6174
Greenish yellow
Yellowish green
Bluish red
Reddish blue
Bluish green
Greenish blue
Yellow
Red
Blue
Green
Reddish yellow
Yellowish red
Principles of Colour
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The CIE Lab Formula
a*C* = “intensity” differenceH* = shade differenceL* = lightness difference
a* = red/ green - Colourfulnessb* = yellow/blue- Colourfulness
L* = Lightness
Derived designation:
L*
b*
E*ab = ( L*)2 + ( a*)2 + ( b*)2
E*ab = ( L*)2 + ( H*)2 + ( C*)2
22 *)(*)(* baC +=
Chroma Shade/Hue angle
⎟⎠⎞
⎜⎝⎛= −
**1
abtanh ab
Principles of Colour
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CIElab System
- dH + Tolerances
dC dH/=/ Equal 0.00 – 0.10 0.00 – 0.10
1 Trace 0.11 – 0.30 0.11 – 0.20
2 Slightly 0.31 – 0.80 0.21 – 0.50
3 Noticeably 0.81 – 1.40 0.51 – 0.80
4 Distinctly 1.40 – 2.20 0.81 – 1.40
5 Considerably 2.21 – 3.00 1.41 – 2.00
6 substantially > 3.01 > 2.00
Chroma & Lightnessgreener Blue redder
Lighter + dL - Darker+ dC -yellower Green Dullerbluer Brighter
bluer Violet redder
bluer Red yellower
redder Orange yellower
redder Yellow greener
Colour measurement
Principles of Colour
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Definition of Colourants
Slide 53
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Definition of Definition of ColourantsColourants
Bulls and horses in a cave near
Lascaux (France)
Egyptian receptaclewith painted boatand ornaments
Definition of Colourants
Slide 54
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Egypt 1500 bc . Painting on limestone.
Definition of Colourants
Slide 55
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Egypt 1500 bc . Painting on limestone.
Definition of Colourants
Slide 56
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Egypt 1500 bc . Painting on limestone.
Definition of Colourants
Slide 57
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A modern pigment shop in Venice, Italy, where the "traditional" painter/artist can buy pigments to mix into paints themselves.
Definition of Colourants
Slide 58
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PigmentsInsoluble in mediumHigher light/weather fastnessBetter chemical resistanceMore opaque
DyestuffsSoluble in mediumLimited light/weather fastnessHigh colour strengthLimited chemical fastnessLimited migration fastnessHigh transparency
What’s the
What’s the
difference
difference ??
Pigments and dyes
Definition of Colourants
Slide 59
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according to shade (DIN 55944)
organic
Pigments
White Pigments
Colored Pigments
Black Pigments
Lustre Pigments
Fluorescent Pigments
Dyes
inorganic
Colorants
Pigments Dyes
no commercialprominence
Colored PIgments
Black Pigments
Lustre Pigments
physicallyimpossible
Colored Dyestuffs
Black Dyestuffs
physicallyimpossible
Classification of Colorants
Fluorescent Dyestuffs
Fluorescent Pigments
Definition of Colourants
Slide 60
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Characteristics of Inorganic & Organic Pigments
Characteristics of Organic & Inorganic PigmentsCharacteristic Organic Pigments Inorganic Pigments
Primary particles Small LargeScattering Weak StrongAbsorption High LowSurface High area / hydrophobic Small area / hydrophilicColour (hue) Bright Dull ► brightLight/weatherfastness Poor ► excellent Good ► excellentTinting strength Strong WeakOpacity Transparent ► opaque OpaqueSolvent fastness Poor ► excellent ExcellentChemical fastness Good ► excellent Poor ► excellentDispersibility Fair ► excellent Good ► excellentHeat stability Good ► excellent Good ► excellentToxicology Mostly excellent Heavy metals
Definition of Colourants
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Types of Inorganic Pigments
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White pigments.
*Organic coating is destroyed at over 280°C .
Titanium dioxide - rutile
Titanium Dioxide - anatase Zinc sulphide
Colour-Index P.White 6 P.White 6 P.White 7Formula TiO2 TiO2 ZnSHeat resistance °C 280/300 280/300 300Refraction index n 2,75 2,55 2,35Scattering index 1 1,5 2Dispersibility very good good very goodAbrasion abrasive less abrasive low abrasiveParticle size (µ) 0,1-1,0 0,1-1,0 1Coating * organic/inorganic organic/inorganic no
Manufacturing process Sulphate/Chloride Sulphate chemical reaction
Shade a little yellowish a little bluish bluish
Types of Inorganic pigments
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Lead chromate pigments
Colour area
Name Formula Colour-Index
Chrome yellow Pb(Cr,S)O4 P. Yellow 34 0,5-1,0
Chrome yellow PbCrO4 P. Yellow 34 0,5-1,0
Molybdate red Pb(Cr,Mo,S)O4 P. Red 104 0,5-1,0
Particle size (µ)
Properties: Lead chromate pigments have different crystal modifications: rhombic-monoclinic-tetragonal. They are distinguished by medium to high heat resistance, high covering power and brilliant shades. For fastness properties, they are coated with inorganic compounds e.g. silicates, alumina. This allows improvements on their resistance to light, heat, weathering and chemicals which varies from good to excellent. Their resistance to acid/alkaline is moderate.
Disadvantage:Disadvantage: Not for food packaging materials, environmentNot for food packaging materials, environment--polluting, toxicpolluting, toxic
Types of Inorganic pigments
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Cadmium pigments
NameName FormulaFormula ColourColour--IndexIndex particle size (µ)particle size (µ)
Cadmium yellow greenish (Cd,Zn)S P. Yellow 35 0.2-2
Cadmium yellow reddish CdS P. Yellow 37 0.2-2
Cadmium orange Cd(S,Se) P. Orange 20 0.2-2Cadmium red Cd(S,Se) P. Red 108 0.2-2
Properties: Excellent general properties.Bright, clean fullshades.Lithopone types contain BaSO4Greenish types have lower weather resistance.
Manufacturing is carried out in a calcining process at 500-650°C.
Colour area
Disadvantage:Disadvantage: Not for food packaging materials, Not for food packaging materials, environmentenvironment-- polluting.polluting.
Main usage is in plastics or ceramics.
Types of Inorganic pigments
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Mixed phase / Metal complex pigmentsMixed phase / Metal complex pigmentsName Formula Colour-Index Particle size (µ)
Nickel titanium yellow
(Ti,Ni,Sb)O2 P. Yellow 53 0.4-0.7
Chrome titaniumyellow
(Ti,Cr,Sb)O2 P. Brown 24 0.2-0.4
Cobalt blue Co(Al,Cr)O4 P. Blue 36 0.2
Cobalt green (Co,Ni,Zn)(Ti,Al)O4 P: Green 50 0.5
Zinc iron brown ZnFe2O4 P. Yellow 119 1.0-2.6
Spinel black Cu(Fe,Cr)2O4 P. Black 22 1.4-3.9
Properties: Excellent fastness properties in all concentrations
Manufacturing is carried out in a calcining process at approx. 1000°C.
Types of Inorganic pigments
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Oxide Pigments
Colour area
Name Formula Colour-Index particle size (µ)
Iron oxide yellow FeOOH P. Yellow 42 0.1-0.6
Iron oxide red Fe2O3 P. Red 101 0.1-0.6
Iron oxide black
Fe3O4 P. Black 11 0.6-1.6
Chrome oxide greenCr2O3 P. Green 17 0.3-2.0
Properties: Iron oxide yellow is limited in heat stability (180°C). All others have excellent fastness properties. All pigments are abrasive.
Disadvantage: The thermal ageing of polypropylene and PVC is negatively affected by the use of iron oxide pigments.
Types of Inorganic pigments
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Ultramarine/ Manganese pigments
Excellent light fastnessExcellent heat resistanceShading pigment
Properties: Manganese violet
Excellent light fastnessExcellent heat resistanceDispersibility difficult
Properties: Ultramarine blue
Sensitivity to acid and alkalisVery weak tinting power
Sensitivity to acidRelatively high water contentModerate weather fastness
Colour area
Name Formula Colour IndexParticle size (µ)
Ultramarine blue Na6Al6Si6O24(Na S2-4) P. Blue 29 0.3-8.0
Ultramarine violet Na6Al6Si6O24(NA S2-4 ) P. Violet 15 0.3-8.0
Manganese violet NH4Mn P2O7 P. Violet 16 0.3-8.0
Types of Inorganic pigments
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Black pigments
Properties: Carbon black.
Improves the fastness to weathering of polymers
Multipurpose applicationsLow cost pigmentExcellent fastness properties
Improves the electrical conductivity of polymers
HygroscopicDispersibility is difficultThe tenacity of polymers is negatively affected
Carbon black C P. Black 7 0.01-0.1
Iron oxide black Fe3O4 P. Black 11 0.6-1.6
Spinel black Cu(Fe,Cr)2O4
P. Black 28 1.4-3.9
Name Formula Colour Index Particle size (µ)Types of Inorganic pigments
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Name Formula Colour-IndexAluminium Al P. Metal 1Copper Cu P. Metal 2
Cooper/Zinc-alloy Cu-Zn P. Metal 2
Metal pigments
Aluminium powder is explosive in mixturewith air, dust-free metal pastes are availableSolvents where used smell like white spirit.The particle size and shape is variedLarge size particle - good metal effectSmall particle - high covering power
Properties:
Disadvantage:Due to their flake structure, all metal pigments are shear sensitive.Bronze pigments can oxidise/tarnish
Types of Inorganic pigments
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Effect pigments
Mica with TiO2-coating Pearl effect pigmentsPearl effect pigments
Mica with iron oxide andtitanium dioxide coatings
Interference pigmentsInterference pigments
Disadvantage: Because of their flake structure, all micaceous pigments are shear sensitive.Require high loadings to be effective
Types of Inorganic pigments
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Fillers
1.Carbonates1.Carbonatesnatural calcium carbonate from fossilsnatural calcium carbonate, crystallinechemical calcium carbonatenatural calcium-magnesium carbonate
2. 2. SulphatesSulphatesnatural barium saltssynthetic barium salts
3. Silicates3. Silicatesnatural magnesium silicate hydratenatural aluminium silicate hydrate
natural calcium aluminium silicate hydrate
ChalkCalcite, MarbleCCPDolomite
BarytesBlanc fix
French chalkKaolin, China ClayMuscovite (Glimmer)
Types of Inorganic pigments
Public
ASEAN Regional Technical ServicCorporate Presentation
Types of Organic Pigments
Slide 74
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
History and Chemistry of Organic Pigments
1899 Pigment Red 1. The first true organic pigment.1900 to 1930’s. Huge range of azo pigments
developed. These products met the demands of the colour using industries.
1950’s. The discovery of plastics and the requirement for automotive stoving paints led to the development of polycyclic and higher fastness azo pigments.
1960’s to the present saw the improvement in the physical characteristics of pigments like improved opacity, better dispersion properties etc. A few new chromophores were also developed.
Types of Organic pigments
Slide 75
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
What are organic pigments?Organic pigments are a system of conjugated double bonds connected by chromophores and modified by substituent groups
Chromophores : - N = N - - C = N -- C = O - N = O- C = C -
Substituent Groups ::Auxchromes : electron donors : CHCH33 OH OH
ArNHArNH22electron acceptors : COOH SOCOOH SO2 2
COORCOORHypsochromes : BrBr ClCl
Types of Organic pigments
Slide 76
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
A chromophore complex formsthe basic organic pigment
molecule
- -- - N = N -
NO2
NO2
OH
2,4 - Dinitroaniline+
B -Naphtol
Pigment Orange 5
Types of Organic pigments
Slide 77
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
There are 5 basic raw materials :
-H3C -H3C - CH3
Benzene
C6H6
Naphthalene
C10 H8
o, m, p - Xylene
C8H10
Toluene
C7H8
Anthracene
C14H10
Types of Organic pigments
Slide 78
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
Modified by a variety of chemical processes e.g.
Substitution AdditionNitration SulphonationOxidation ReductionHalogenation Alkali fusionHydrolysis AcylationAlkylation
In many cases there can be multiple reactions required in the preliminary synthesis of the raw materials as well as the finalpigment synthesis
Types of Organic pigments
Slide 79
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
And further modified by a series of physical processes ……….
• Heat• Dissolution and re-precipitation in
organic solvent or aqueous media• Pressure• Surface treatment
These are usually carried out under carefully controlled conditions and can affect :
Types of Organic pigments
Slide 80
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
Size and distribution
Equivalent diameter (µm) Equivalent diameter (µm)
Vol
ume
porti
on (%
per
siz
e cl
ass)
Vol
ume
porti
on (%
per
siz
e cl
ass)
Vol
ume
dist
ribut
ion
(%)
Vol
ume
dist
ribut
ion
(%)
Narrow particle size distribution achieved by lower finishtemperature for ink jet application
Types of Organic pigments
Slide 81
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
Shape
P.R.122Mixed crystal
P.R.122Surface modified
Rod likeTransparentLow viscosity
cubicHighly transparentHigher viscosity
Viscosity design by modified shape
Types of Organic pigments
Slide 82
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
The Surface• Influence of the polarity of the pigment on the wetting behaviour
Type A – hydrophobic – floating on thewater surface
Type B – hydrophillic – excellent wettingin water
Surface design for perfect fit
Types of Organic pigments
Slide 83
Public
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Organic Pigments -The Basics
Tim Boyce
Intermediates Derived From NitrobenzeneIntermediates Derived From Nitrobenzene
Slide 84
Public
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Organic Pigments -The Basics
Tim Boyce
Pigments or Dyes ???
Pigments and dyes often have a similar molecular structure
Solubilising or insolubilising constituents determine the category
Insolubilising groups : carbonamide groups, nitro groups or chlorine (azo pigments), nitrogen, chlorine and bromine for polycyclic pigments. Polar substituents decrease solubility in non polar solvents whilst increased substitution increases insolubility
Solubilising groups : long chain alkyl, alkoxy or alkylamino groups and sulphonic acid functions
Many pigments have partial solubility depending on the application medium,solvents and the processing conditions (particularly temperature)
For pigments, fastness properties are a function of both their chemical structure and, most importantly, their physical characteristics (crystallinity, particle size and distribution etc) whereas for dyes it is purely their chemical structure
Types of Organic pigments
Slide 85
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
Pigment Chemistry
Three options to reduce solubility:
Laked pigments : Chromophore F with acidic groups. SO3- / CO2
-
Reaction with metal salt
Large molecules : From Monoazo to Dis-azo
F-SO3- / F-CO2
- M+
------>F-SO3
- M+ / F-CO2- M+
---->-N=N- -N=N-A-N=N-
New Substitutients for example: -CONH- group
-CONH- group
Types of Organic pigments
Slide 86
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce NN
OHCH3
NO2
NN
OH
OCH3
Cl
NO2
CH3
H
ON
O
N NH
HHCONH2
HOC2H5
H
ON
O
N NH
HH NO2
OCH3
N N
O N
NON
OH
H H
H
Solvent Red 1 Pigment Red 3 Pigment Red 14 Pigment Red 170 Pigment Red 171Fat Red G Hansa Red B Permanent Novoperm Red Permanent
Bordeaux FGR F5RK Bordeaux HFM
FullshadeLightfastness 7Overspray 2
FullshadeLightfastness 6-7Overspray 3
1:85 TiO2Lightfastness 4
FullshadeLightfastness 7-8Overspray 5
1:46 TiO2Lightfastness -
1:55 TiO2Lightfastness 4-5
FullshadeLightfastness 6Overspray 5
1:80 TiO2Lightfastness 6
Effect of substitution on colour and fastness properties
Slide 87
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
Effects of Pigment Chemistry
Improve fastness propertiese.g. increased substitution
Shade e.g. new chromophores
Types of Organic pigments
Slide 88
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
Classical Azo
Laked
Quinacridone
Phthalocyanine
Perylene
Anthraquinone
Dioxazine
Isoindolinone
Thioindigo
DPP
Lake Red C
Toners
Unlaked
Hansa
Diazo
Monoazo
Special Azo
Naphtols
Azo condensation
Benzimidazolone
Triphenylmethane
Classes of synthetic organic pigments
Azo Polycyclic
Types of Organic pigments
Slide 89
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
Chemistry Yellow Orange Red Brown Violet Blue Green Black
AZO
Monoazo X X X X X
Diazo X X X X X
Azo condensation X X X X
Azo salt X X X X
Azo metal complex X X X
Benzimidazolone X X X X
POLYCYCLIC
Phthalocyanone X X
Anthraquinone X X X X X X X
Quinacridone X X X
Dioxazine X
Perylene X X
Perinone X
Pyranthrone X
Indigoid X X X X
Thioindigo X
Isoindolinone X X X
MISCELLANEOUS
Nitro X
Nitroso X
Quinoline X
Azine X
Basic dye complexes X X X X X X X
Types of Organic pigments
Slide 90
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
Azo Pigments Polycyclic Pigments
MonoazoDisazoBeta-NaphtholNaphthol ASRed Azo LakesBenzimidazoloneDisazo Condensation
PhthalocyanineQuinacridonePerylene/PerinoneIsoindolinone/IsoindolineDioxazineTriphenylmethaneDiketo-Pyrrolopyrrole DPP
Pigment classes
Types of Organic pigments
Slide 91
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
Azo-Pigments
Monoazo : R2-N=N-R3 C.I.CH3
NN
+
O O
NNH
O
O
NN
NOH
O
CH3
O
NN
NOH
O
Cl
ONH
OCH3
NN
OH O
OS
CH3
OOO
Mn2+
NN
OH NH
O
NO
OO
CH3NH
NH O
Monoazo-Yellow
Naphtol AS
Benzimidazolone
β-Naphtol
BONS laked
Pigment Yellow 1
Pigment Red 14
Pigment Red 171
Pigment Red 3
Pigment Red 48:4
Types of Organic pigments
Slide 92
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
Azo-Pigments
Dis-Azo : R2-N=N-R3-N=N- R2 C.I.
Diarylyellow
Disazo-konden-sation
Pigment Yellow 83
Pigment Red 144
Cl
Cl
NNN
NNH
O
CH3
O
OCH3
NH
OO
O Cl
Cl
O
O
CH3CH3
CH3
CH3
Cl
Cl
NN
OH O
NH
NH
ClO
NN
Cl
Cl
OH
Types of Organic pigments
Slide 93
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
Polycyclic Pigments
Phthalocyanin Pigment Blue 15
Pigment Red 254
N
N
N
N
N
N
N
N
Cu
Chinacridone
Dioxazine
Diketo-Pyrrolopyrrol DPP
NH
NH
O
O
Pigment Violet 19
Pigment Violet 23
O
N
N
O
Cl
Cl
N
N
H5C2
C2H5
NH
NH
O
O
Cl
Cl
Types of Organic pigments
Slide 94
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
Polycyclic Pigments
Isoindolin Pigment Yellow 139
Pigment Red 179
NH
NH
NH NH
NHO
O
OO
O
O
Isoindolinon
Perylene
N NCl
Cl
ClCl
O OCl
Cl
Cl
Cl Pigment Yellow 110
N N
O
O
O
O
CH3CH3
Types of Organic pigments
Slide 95
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
Azo PigmentsChemical structure and fastness properties
Pigment Class Lightfastness Migration fastness
monoazo fair ►very good poor
Β-Naphtol good ►very good poor
Naphtol AS good ►very good poor ►good
BONA, laked good ►very good good
Benzimidazolone excellent excellent
Diarylide fair ►very good good ►very good
Disazocondensation good ►very good Very good ►excellent
Triphenylmethane poor poor
Types of Organic pigments
Slide 96
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
Polycyclic PigmentsChemical structure and fastness properties
Pigment Class Lightfastness Migration fastness
Dibromoanthanthrone excellent excellent
Phthalocyanine excellent excellent
Quinacridone excellent excellent
Diketo-Pyrrolopyrrole excellent excellent
Isoindolinone Very good ►excellent Very good ►excellent
Perylene/Perinone Very good ►excellent Very good ►excellent
Dioxazine Very good ►excellent Very good ►excellent
Isoindoline Very good ►excellent Very good ►excellent
Types of Organic pigments
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Their fastness properties vary considerably.Only few pigments are suitable for shading.
Colour area
Monoazo pigments range from greenish yellow to bluish red. Can be pure monoazo (Hansa, Naphtol) or laked/toner.
The dispersibility is generally good.
P.Y.1, P.Y.3, P.Y.73, P.Y.74, P.Y.75, P.Y.97, P.O.5, P.Y.191, P.R.3, P.R.48, P.R.49, P.R.53, P.R.57, P.R.112, P.R.170, P.R.9, P.R.146, P.R.12
Monoazo pigments
Types of Organic pigments
Slide 98
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce Pigment Red 112 ( C.I. : 12370 )
3
CONH
CH
HOCl
Cl
Cl
N = N
2,4,5 - trichloraniline
2-hydroxy-2-naphtho-ortho-toluidide
Monoazo pigments
Types of Organic pigments
Slide 99
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
N
RD5
RD4
RD2
H RK2
RK5
O O
CH3
N N
RK4
C.I. Name Const. No. R2 R4 R5 R2 R4 R5
P.Y.1 11680 NO 2 CH 3 H H H H
P.Y.3 11710 NO 2 Cl H Cl H H
P.Y.73 11738 NO 2 Cl H OCH 3 H H
P.Y.74 11741 OCH 3 NO2 H OCH 3 H H
P.Y.97 11767 OCH 3SO 2 NH-C 6 H 5
OCH3 OCH 3 Cl OCH 3
D D D K K K
Monoazo (Hansa) yellow pigments
Types of Organic pigments
Slide 100
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
NN
OH
R4
R2
C.I. Name Const. No. R2 R4
P.O.5 12075 NO2 NO2
P.R.4 12085 Cl NO2
P.R.3 12120 NO2 CH3
Monoazo (Hansa) red pigments(β Naphtols)
Types of Organic pigments
Slide 101
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
RD5
RD4
RD2
R2K
R4K
ON
O
N NH
R5K
H
C.I. Nam e Const. No. R 2 R 4 R 5 R 2 R 4 R 5
P.R.9 12460 Cl H Cl O CH 3 H H
P.R.12 12385 CH 3 NO 2 H CH 3 H H
P.R.14 12380 NO 2 Cl H CH 3 H H
P.R.112 12370 Cl C l C l CH 3 H H
P.R.5 12490 O CH 3 H SO 2N(C 2H 5)2 O CH 3 O CH 3 Cl
P .R.146 12485 O CH 3 H CO NHC 6H 5 O CH 3 Cl O CH 3
P.R.170 12475 H CO NH 2 H O C 2H 5 H H
P.R.188 12467 CO O CH 3 H CO NHC 6H 3-C l2(2 ,5) O CH 3 H H
P.R. 253 Cl SO 2NHCH 3 Cl CH 3 C l H
P.O . 74 C l SO 2NHCH 3SO 2N(CH 3)2
C l H Cl H
D D D K K K
Monoazo pigments -Naphtols AS
Types of Organic pigments
Slide 102
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
NOH
NS
O
O
O
CH3Cl
Ba2+
OH O
NH
NN
CH3
NH
O
SO
OO
OCH3
Ca2+
NN
OHR4
P.R. 53:1 ( 15585:1 )
P.R. 247 ( 15915 )
R2
R5
O
O
M2+
C.I. Name Const. No. R2 R4 R5 M
P.R.48:2 15865:2 SO 3- CH3 Cl Ca
P.R.48:3 15865:3 SO 3- CH3 Cl Sr
P.R.48:4 15865:4 SO 3- CH3 Cl Mn
P.R.57:1 15850:1 SO 3- CH3 H Ca
Monoazo red pigments -red azo lakes
Types of Organic pigments
Slide 103
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
Colour area
Disazo pigments
Not recommended for use in applications where the processing temperature exceeds 200°C.
P.Y.12, P.Y.13, P.Y.14, P.Y.17, P.Y.174, P.Y.176, P.Y.188, P.Y.83, P.O.34, P.R.38
Disazo pigments are in the same colour range as monoazo pigments.The lightfastness is good to very good.Very high colour strength i.e. excellent in ink applications.Not suitable in low concentrations in plastics due to high solubility of the pigments.The dispersibility is normally good.
Types of Organic pigments
Slide 104
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
Pigment Yellow 13 ( C.I. : 21100 )
3,3-dichlorobenzidine(3,3-dcb)
2,4- acetoacet -meta-xylidide(aamx)
Disazo pigments
Types of Organic pigments
Slide 105
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
C.I. Name Const. No. R2 R4 R5
P.Y.12 21090 H H H
P.Y.13 21100 CH3 CH3 H
P.Y.14 21095 CH3 H H
P.Y.17 21105 OCH3 H H
P.Y.83 21108 OCH3 Cl OCH3
P.Y.127 21102CH3
OCH3
CH3
H
H
H
P.Y.176 21103CH3
OCH3
CH3
Cl
H
OCH3
P.Y.188 11767CH3
H
CH3
H
H
H
Cl
O
NH
CH3 O
NN
R2
R4
R5
N
CH3
N
O
NH
O
R5R4
R2
Cl
Disazo pigments -AAA arylide
Types of Organic pigments
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Thermal decomposition of diarylide pigments.
• Diarylide pigments partly dissolve above 200°C and split off into a soluble monoazo compound.
•The monoazo compound starts to decompose above 240°C to produce DCB.
• Monoazo dyes and DCB are considered carcinogenic in tests on animals.
A B C>200 °C >240 °C
Diarylidepigment
soluble monoazocompound (coloured)
Note : below 200’C diaryl pigments meet consumer goods regulations
DichlorbenzidineDCB
Types of Organic pigments
Public
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Organic Pigments -The Basics
Colour area
Benzimidazolone pigments range from greenish yellow, orange to bluish red.Mostly high fastness properties. Some pigments have very good weathering fastness.Good to excellent migration fastness.
The dispersibility is generally very good
P.Y.120, P.Y.151, P.Y.154, P.Y.180, P.Y.181,P.O.36, P.O.62, P.R.175, P.R.176, P.R.185,P.R.208, P.V.32, P.Br.25
Benzimidazolone pigments
Types of Organic pigments
Slide 108
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
RD5
RD4
RD2 CH3
N
O
NO N
NO
NR3D
H H
H
C.I. Name Const. No. R2 R3 R4 R5
P.Y.120 11783 H COOCH3 H COOCH3
P.Y.151 13980 COOH H H H
P.Y.154 11781 CF3 H H H
P.Y.175 11784 COOCH3 H H COOCH3
P.Y.194 11785 OCH3 H H H
P.O.36 11780 NO 2 H Cl H
P.O.62 11775 H H NO 2 H
D D D D
Benzimidazolone yellow and orange pigments
Types of Organic pigments
Slide 109
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
RD5
RD4
RD2
N N
O N
NON
OH
H H
H
C.I. Name Const. No. R2 R4 R5
P.R.175 12513 COOCH3 H H
P.R.176 12515 OCH3 H CONHPh
P.R.185 12516 OCH3 SO 2NHCH3 CH3
P.R.208 12514 COOC4H9 H H
P.V.32 12517 OCH3 SO 2NHCH3 OCH3
P.Br.25 12510 Cl H Cl
D D D
Benzimidazolone red and brown pigments
Types of Organic pigments
Public
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Organic Pigments -The Basics
Azo condensation pigments range from greenish yellow to bluish red.
Mostly high fastness properties. Some pigments have very good weathering fastness.
Good to excellent migration fastness.
Colour area
The dispersibility in some cases is not easy.
P.Y.93, P.Y.94, P.Y.95, P.Y.128, P.R.144, P.R.166, P.R.214, P.R.220, P.R.242, P.R.248
Azo condensation pigments
Types of Organic pigments
Slide 111
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
N
NH
NH
R4
R2O
N
CH3O
NO
N
CH3
A
AQ
O
Q
OO
C.I. Name Const. No. R2 R4 A Q
P.Y.93 20710 Cl Cl Cl NH-C6H3-2- CH3,3-Cl
P.Y.95 20038 Cl CH3 Cl NH-C6H3-2- CH3,5-Cl
P.Y.128 20037 Cl CH3 Cl NH-C6H3-2-OAr,5-CF3
P.Y.155 200310 H H COOCH3 OCH3
Ar = C6H4-4-Cl
Disazo :Bis AAA Arylide / Yellow azo condensationpigments
Types of Organic pigments
Slide 112
Public
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Organic Pigments -The Basics
Tim Boyce
R2K
R4K
NH
O
NH
O
OHN
OH N
N
N RD2
RD2
RD4
RD4
RD5
RD5
C.I. Name Const. No. R2 R4 R5 R2 R4
P.R.144 20735 Cl H Cl Cl H
P.R.166 20730 Cl H Cl H H
P.R.214 200660 Cl H Cl Cl Cl
P.R.220 20055 CH3 H COOCH2CH2Cl CH3 CH3
P.R.221 20065 Cl H COOCH(CH3)2 Cl Cl
P.R.242 20065 Cl H CF3 Cl Cl
P.R.262 - Cl H Cl CN H
P.Br.23 20060 NO2 Cl H Cl H
D D D K K
Disazo : Red azo condensation pigments
Types of Organic pigments
Public
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Organic Pigments -The Basics
Colour areaColour area
Deep blue shade with excellent colour strength.
The fastness properties are very poor
The dispersibility is very poor and thus they are normally supplied as flushpastes or powder preparations
P.B.56, P.B.61
Used to tone black printing inks for offset applications
Triphenylmethane
Types of Organic pigments
Slide 114
Public
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Organic Pigments -The Basics
Tim Boyce
NH
C+
NH
NH
R2
R2
R2
-O3S
C.I. Name Const. No. R2
P.Bl.56 42800 CH3
P.Bl.61 42765:1 H
Triphenylmethane : Reflex (Alkali) blue
Types of Organic pigments
Public
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Organic Pigments -The Basics
Colour area
Shade from yellow to orange to red , good colourstrength.
The fastness properties are good to excellent.
The dispersibility is generally good.
Reaction with alkaline additives can cause discoloration and a reduction in fastness properties.
P.Y.109, P.Y.110, P.Y.139, P.Y.173, P.Y.185 P.O.61, P.O.66, P.O.69, P.R.260
Isoindolinone / Isoindoline
Types of Organic pigments
Slide 116
Public
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Organic Pigments -The Basics
Tim Boyce
Isoindolinone :
NHCl
Cl
ClCl N
N
CH3
N
NH
ClCl
ClClO
NHCl
Cl
ClCl O
N N
NH
ClCl
ClClO
P.Y. 109 ( 56284 )
P.Y. 110 ( 56280 )
Isoindoline :
H
HN
NO
O
O
N
N
NO
O
O
H H
H
NH
NH
O
O
NH N
H
OO
N
CH3
P.Y. 139 ( 56298 )
P.Y. 185 ( 56290 )
Isoindolinone / Isoindoline
Types of Organic pigments
Public
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Organic Pigments -The Basics
Greenish yellow pigments.
Excellent fastness properties.
Colour area
P.Y.138
Quinophthalone
Types of Organic pigments
Public
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Organic Pigments -The Basics
Yellowish to bluish red, pink and redYellowish to bluish red, pink and red--violet violet pigments.pigments.
Excellent fastness properties.Excellent fastness properties.
Suitable as shading pigment.Suitable as shading pigment.
Colour area
Optimum dispersion is often difficult.Optimum dispersion is often difficult.
P.R.122, P.R.202, P.R.207, P.R.209, P.V.19,P.R.206, P.O.48, P.O.49, P.V.42
Quinacridone
Types of Organic pigments
Slide 119
Public
ASEAN Regional Technical Service
Organic Pigments -The Basics
Tim Boyce
N
N
RR
RR O
R
R
RR
OH
H
1
2
3
4
11
10
9
8
C.I. Name Const. No. R2 R3 R4 R9 R10 R11
P.V.19 73900 H H H H H H
P.R.122 73915 CH3 H H CH3 H H
P.R.202 73907 Cl H H Cl H H
P.R.207 73905 H H Cl H H Cl
P.R.209 73905 H Cl H H Cl H
P.O.49 - unsubst. Quinacridone+ Quinacridonequinone
Quinacridone
Types of Organic pigments
Public
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Organic Pigments -The Basics
Yellowish to bluish red shade.Excellent fastness properties.Suitable as shading pigment.
Colour area
The dispersibility is generally fair to good
P.R.123, P.R.149, P.R.178, P.R.179, P.R.190,P.R.224, P.V.29
Perylene
Types of Organic pigments
Public
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Organic Pigments -The Basics
Brilliant orange pigment.
Excellent lightfastness.High weathering resistance in reduced shades.
Colour area
Not suitable as shading pigment Not suitable as shading pigment in plasticsin plastics( solubility) but ( solubility) but in paintsin paints is best suited for is best suited for shading.shading.
The dispersion is generally good.
P.O.43, P.R.194
Perinone
Types of Organic pigments
Slide 122
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Organic Pigments -The Basics
Tim Boyce
Perylene :
NN
O
OO
O
C.I. Name Const. No. Q
P.R.149 71137 3,5Me2-Ph
P.R.178 71155 4-Ph-N=N-Ph
P.R.179 71130 Me
Perinone :
N O
N
N
NO
P.O. 43( 71105 )
Perylene / Perinone
Types of Organic pigments
Public
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Organic Pigments -The Basics
Brilliant yellowish red pigment.
Excellent light and weathering resistanceat all shade depths
Colour area
The dispersion is generally good.
P.R.168
O
O
Dibromoanthranone
Types of Organic pigments
Public
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Organic Pigments -The Basics
Reddish blue shade.Excellent fastness properties.
Colour area
P.B.60
Optimum dispersion is often difficult.
Indanthrone
Types of Organic pigments
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Organic Pigments -The Basics
Orange to bluish red pigments.
Excellent fastness properties.
The dispersion is generally good.
P.O.71, P.O.73, P.R.254, P.R.255, P.R.64, P.R.270, P.R.272
Colour area
Diketo-pyrrolopyrrole
Types of Organic pigments
Slide 126
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Organic Pigments -The Basics
Tim Boyce
NH
NH
O
O
R3
R3
R4
R4
C.I. Name Const. No. R3 R4
P.O.71 561200 CN H
P.O.73 561170 H C(CH3 )3
P.R.254 56110 H Cl
P.R.255 561050 H H
P.R.264 561300 H Ph
Diketo-pyrrolopyrrole
Types of Organic pigments
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Organic Pigments -The Basics
Reddish and greenish blue pigments.Yellowish and bluish green pigments.Excellent fastness properties.Universal suitability, low coloration costs
Colour area
The dispersibility can be difficult.
P.B.15, P.B.15:1, P.B.15:2, P.B.15:3,P.B.15:4, P.B.15:6, P.G.7, P.G.36
Phthalocyanine
Types of Organic pigments
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Tim Boyce
N
N N
N
NNNN
Cu
N
N N
N
NNNN
Cu
N
N N
N
NNNN
Cu
C .I. N a m e m o d if ic a tio n H a lo g e n s m o d . s ta b il iz e d flo c c u la t io n
P .B l. 1 5 α - n o -
P .B l. 1 5 :1 α 0 .5 -1 C l y e s u n s ta b le
P .B l. 1 5 :2 α 0 .5 -1 C l y e s s ta b le
P .B l. 1 5 :3 β t ra c e s - u n s ta b le
P .B l. 1 5 :4 β t ra c e s - s ta b le
P .B l. 1 5 :6 ε t ra c e s y e s
P .G r. 7 - 1 4 -1 5 C l
P .G r. 3 6 - 4 -9 B r,8 -2 C l
Copper (II) complex oftetraazatetrabenzoporphine
Phthalocyanine
Types of Organic pigments
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Very reddish violet pigment.Excellent fastness properties.
Colour area
Not suitable in low concentration Not suitable in low concentration in plastics due to solubility.in plastics due to solubility.
The dispersion is often difficult.The dispersion is often difficult.
P.V.23
Dioxazine
Types of Organic pigments
Slide 130
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Tim Boyce
N O
N
N
O N
Cl
Cl
P.V. 23 ( 51319 )
Dioxazine
Types of Organic pigments
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ASEAN Regional Technical ServicCorporate Presentation
Synthesis and Production of Azo
Pigments
Slide 132
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Organic Pigments -The Basics
Tim Boyce
Azo pigments are named for containing an azo-group
-N=N-Two nitrogen-atoms are
connected with a double bond.
Synthesis and Production of AzoPigments
Slide 133
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Tim Boyce
There can be one Azo group in so called monoazo pigments
NNCH3
OHNO2
Hansa Red BPigment Red 3
Synthesis and Production of AzoPigments
Slide 134
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Tim Boyce
or two azo groups, then it is called a disazopigment (also called diaryl or diarylide)
NH
O
CH 3
O
NN N
NC H 3
O
ONH
Cl Cl
Permanent Yellow DHGPigment Yellow 12
You can also think about molecules with more then two Azo-groups. This is actually done in the
synthesis of azo dyes
Synthesis and Production of AzoPigments
Slide 135
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Tim Boyce
Diazotization of an aromatic amine to form the diazonium compound
CH3
NN
NO2
+
Cl- + NaCl + 2 H2O
NH2
CH3
NO2
+ 2 HCl + NaNO2
The unstable diazonium compound has to be cooled with ice to 5-7°C to avoid any side reaction
Synthesis and Production of AzoPigments
Slide 136
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Tim Boyce
Dissolving of the coupling component
ONa
+ H2O
There is a huge variety of coupling components but the technically most significant groups are :•compounds containing activated methylene groups•pyrazolone derivates and•2-Hydroxynaphthalene and its 3-carboxylic acid derivatives
+ NaOH
OHSynthesis and Production of AzoPigments
Slide 137
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Organic Pigments -The Basics
Tim Boyce
CH3
NN
NO2
+
Cl-ONa
NNCH3
OHNO2
+ NaCl
Hansa Red B, P.R. 3
Synthesis of the pigment
By coupling the two components, the pigment precipitates as primary particles.There is no longer a solution but a suspension.
couplingSynthesis and Production of AzoPigments
Slide 138
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Tim Boyce
Disazo Pigment
+ +
Coupling kettle
Dissolving kettle
Diazokettle
+
+
KETTLE 2
CHC=OCH
2
3
NH C=O O=C NHCHC=OCH AAA
2
3
KETTLE 2
Cl_ +
N ≡ N
Cl Cl
N ≡ N
+
Cl_
DCB
KETTLE 1
DIARYLIDE YELLOW ( P.Y.12 )
ClClHN C=O
C=O
CH CH
O=C NH
C=O
HC N = N N N CH=
3 3
PRECIPITATION
2 NaOH
2 NaCl
2 H2O
+
Dissolving kettle
Synthesis and Production of AzoPigments
Slide 139
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Organic Pigments -The Basics
Tim Boyce
Reactor vessel –Normally a sealedunit and as fully automated as possible
Synthesis and Production of AzoPigments
Slide 140
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Tim Boyce
During coupling process, different conditions have to be control
TemperaturepH valueTime
These controlled conditions will have major effects on the synthesis, and therefore on the quality of the pigment
Synthesis and Production of AzoPigments
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Tim Boyce
important process to reach optimum application properties
thermal treatmentheating the crude pigment
suspension in water and/or organic solvents
surface treatmentadding appropriate auxiliaries
with different chemical structures
Optimizing the physical properties of the pigment, such as:Crystal shapeCrystal sizeCrystal qualityParticle size distribution
Finishing
Synthesis and Production of AzoPigments
Slide 142
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Organic Pigments -The Basics
Tim Boyce
Slide 143
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Organic Pigments -The Basics
Tim Boyce
Synthesis and Production of AzoPigments
Slide 144
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Organic Pigments -The Basics
Tim Boyce
VAPOUR
FILTRATION
H2 O
NaOHCOUPLING COMPONENT
HCl
+ ICE
AROMATIC AMINE
Na NO2
DIAZOTISATIONKETTLE
DISSOLVING OF COUPLING COMPONENT
FILTRATION
COUPLING KETTLE
Synthesis and Production of AzoPigments
Slide 145
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Organic Pigments -The Basics
Tim Boyce PRESSCAKEGRANULES
VAPOUR
PUMP
NAUTA BLENDER
DRYING
DRYING OVEN
FILTRATIONFILTER
GRANULATOR
FINISHKETTLE
Synthesis and Production of AzoPigments
Slide 146
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Tim Boyce
Filterpress with falling filtercakeBy opening the filterplates,the filtercake falls to a beltand is transferred to thenauta-blender.
Drum filter withfiltercake
The filter sucks up thesuspension, the liquor moves through the clothand leaves behind the filtercake.
Synthesis and Production of AzoPigments
Slide 147
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Tim Boyce
Granulation in frontof belt dryerTo give a large surface area to the filtercake it is granulatedbefore drying.
Dry pigment granules After being dried, the priment granulesfall from the beltdryerto the mill.
Synthesis and Production of AzoPigments
Slide 148
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Organic Pigments -The Basics
Tim Boyce
1 2 3 4
BLENDER
MILLING
STORAGE BINS
PIGMENT POWDER
JET - MILL
Synthesis and Production of AzoPigments
Public
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Properties of Organic Pigments
Slide 150
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Organic Pigments -The Basics
Tim Boyce
Properties of organic pigmentsPattern card dataColour IndexStandard Shade DepthTinting StrengthPigment Physics
– Particle size and distribution– Crystallography and shape– Specific surface area
Dispersion of organic pigmentsFlocculationFastness properties
– Migration / solvent fastness– Heat stability– Lightfastness– weatherfastness
Properties ofOrganic Pigments
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Tim Boyce
☺ Colour Index
☺ Tint Strength☺ Physical Properties
☺ Colour & Shade Depth
☺ Fastness Properties
Pattern Card Data
Properties ofOrganic Pigments
Slide 152
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Organic Pigments -The Basics
Tim Boyce
Properties ofOrganic Pigments
Slide 153
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Organic Pigments -The Basics
Tim Boyce
Properties ofOrganic Pigments
Slide 154
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Organic Pigments -The Basics
Tim Boyce
Properties ofOrganic Pigments
Public
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Organic Pigments -The Basics
By producer, with trade nameStructure (optional)PropertiesApplication field
Report to Colour Index :
Constitution numberGeneric nameTrade name
Listing in Colour Index :
According to application, properties, shade and structure.
Classification in Colour Index :
Generic name
Constitution number
Nomenclature system for pigments and dyestuffs
The Colour Index is published by the Society of Dyers and Colorists (GB) and the American Association of Textile Chemists and Colorists.
Colour Index
4th EDITION: online ( www.colour-index.org )different search modes
Properties ofOrganic Pigments
Public
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Organic Pigments -The Basics
Colour Index
Generic Names
CI Class Shade Number
PigmentSolvent
VioletRed
19135
PigmentCI Class
Dye Solvent, reactive, vat, basic,Acid, direct, disperse
Shade yellow, orange, red, violet, blue, green,brown, black, white
Number continuous
Generic NameProperties ofOrganic Pigments
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Tim Boyce
Chemical Constitution Constitution Number
Nitroso 10000 – 10299
Nitro 10300 – 10999
Monoazo 11000 – 19999
Disazo 20000 – 29999
Stilbene 40000 – 40799
Diphenylmethane 41000 – 41999
Triphenylmethane 42000 – 44999
Xanthene 45000 – 45999
Acridine 46000 – 46999
Quinoline 47000 – 47999
Methine 48000 – 48999
Thiazole 49000 – 49399
Indamine 49400 – 49699
Indophenol 49700 – 49999
Azine 50000 – 50999
Oxazine 51000 – 51999
Thiazine 52000 – 52999
Anthraquinone 58000 – 72999
Indigoid 73000 – 73999
Phthalocyanine 74000 – 74999
Inorganic pigments 77000 - 77999
Colour Index –Constitution Numbers
Properties ofOrganic Pigments
Slide 158
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Organic Pigments -The Basics
Tim Boyce
Same Colour Index but .......
Permanent Yellow NCG Permanent Yellow NCG 71 Permanent Yellow NCG Permanent Yellow NCG 71
Hansa Brilliant Yellow 5GX Hansa Brilliant Yellow 2GX 70
Novoperm Yellow HR 02 Novoperm Yellow HR 70
Hansa Brilliant Yellow 5GX Hansa Brilliant Yellow 2GX 70
Novoperm Yellow HR 02 Novoperm Yellow HR 70
P.Y.16
P.Y.83
P.Y.74
Properties ofOrganic Pigments
Slide 159
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Tim Boyce
Standard Shade Depth (SD) - DIN 53235
The “depth of shade” is a degree of intensity of visual colourperception. It denotes the visual spacing between a given coloration and a pure white specimen.
With increasing saturation the intensity is higher and with increasing luminosity the intensity of colour perception in general will decrease.
“Standard depth of shade” (SD) is a level of depth of colourwhich is settled by convention.
1/1 SD, 1/3 SD or 1/25 SD which are used for illustration ortesting procedure are standardised according to DIN 53235
The colorimetric calculation is according to CIE-lab system(standardised in DIN 6174)
Properties ofOrganic Pigments
Slide 160
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Tim Boyce
P.Y. 3 P.Y. 83 P.R. 112 P.B. 15:1 P.V. 23
Fullshade Fullshade Fullshade Fullshade Fullshade
1:2.5 TiO2 1:15.3 TiO2 1: 5.5 TiO2 1:12.3 TiO2 1:19.7 TiO2
1:29 TiO2 1:200 TiO2 1: 70 TiO2 1:175 TiO2 1:265 TiO2
1/3 SD
1/25 SD
FS
Standard Shade Depth (SD) - DIN 53235
Properties ofOrganic Pigments
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Tim Boyce
•PRINTING INK : Pigment concentration required to give indicated shade depth at 1.5 g/m2. The lower the figure, the stronger the pigment.
e.g. 7.0g strong (GRX 80) ; > 25g weak (H4G)
•PAINT : Parts of TiO2 needed to bring 1 part of colouredpigment to the indicated shade depth. The larger the figure, the stronger the pigment.
e.g. 1:132 strong (5GX 02) ; 1:26 weak (H3G)
•PLASTIC : The grams of pigment / kg plastic with either5% TiO2 (PVC) or 1% TiO2 (PO) needed to reach the indicated depth
e.g. 2.5g strong (HR) ; 14.59 weak (H3R)
Tinting strengthThe evaluation method is depending very much on the application, thus the information varies in different pattern cards .
Properties ofOrganic Pigments
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Tim Boyce
can influence
can influence
can influence
particle composition
particle size
crystal structure
primary particlesaggregatesagglomerates
colourcolour purityfastness properties
tinting strengthshadehiding power
Pigment physics
Properties ofOrganic Pigments
Public
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Organic Pigments -The Basics
Pigment Green 7 Pigment Orange 43
Pigment Red 247 Pigment Red 144
Enlargement 32 000 X
Organic pigment crystals
Properties ofOrganic Pigments
Public
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Organic Pigments -The Basics
Primary particle
Agglomerates
Aggregates
Smallest unit of a material. Has its properties. In this case a mono crystal.
Bundle of primary particles, coupled on the surface (face to face). The surface is smaller than the surface of all single primary particles together. There is no inner accessible surface.
Primary particles and aggregates coupled at the corners and edges. The surface is not much different from the sum of the surface of all particles. The inner surface is accessible.
Particle composition of pigments
Properties ofOrganic Pigments
Slide 165
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Tim Boyce
C.I. Pigment Blue 15
α-modification β-modification
Crystals in same directionSpacing is smallerAngle is smaller
Crystals in alternate directionSpacing is biggerAngle is greater
Crystal modifications
Properties ofOrganic Pigments
P.B.15:1Red shade
P.B.15:3Blue shade
Slide 166
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Tim Boyce
white reduction
β γ
full shade
β γ
Hostaperm RedViolet ER 02 / ERX
Hostaperm RedE3B / E5B 02
Hostaperm RedViolet ER 02 / ERX
Hostaperm RedE3B / E5B 02
C.I. Pigment Violet 19
Crystal modifications
Properties ofOrganic Pigments
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Tim Boyce
SEM-micrograph of powder pigmentsC.I. Pigment Yellow 83
®Novoperm Yellow HRSpecific surface area 69 m2/gAverage partice size 40 nm
®Novoperm Yellow HR 70Specific surface area 22 m2/gAverage partice size 325 nm
Properties ofOrganic Pigments
Slide 168
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Tim Boyce
Relationship between particle size and shade, opacity and tint strength
Novoperm YellowHR 02
(P.Y.83)
Novoperm YellowHR 70
(P.Y.83)
Novoperm YellowHR 02
(P.Y.83)
Novoperm YellowHR 70
(P.Y.83)Properties ofOrganic Pigments
Slide 169
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Tim Boyce
Relationship between particle size and surface area …………..Cubic dimension Number of particles
in basic cubeSurface Area (m2)
1 cm 1 6 cm2
1 mm 103 60 cm2
1 nm 1012 60000 cm2
Assuming a spherical shape ………….Particle diameter in µ Surface Area (m2/g)
0.4 150.3 200.2 300.1 60
Specific surface area
Properties ofOrganic Pigments
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Tim Boyce
0.000.050.100.150.200.250.300.350.400.450.50
0.1 0.2 0.3 0.4 0.5 0.6microns (u)
K/SP.Y.17P.G.7
Effect of particle size on tint strength
Properties ofOrganic Pigments
Slide 171
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Tim Boyce
Most Monoazo Grades, 70 Series
< 25 sq m/g
Some Quinacridones, Dioxazine Violet,Phthalocyanines
> 55 sq m/g
25-55 sq m/g
Naphtol Grades, some Quinacridones
Typical surface areas
Properties ofOrganic Pigments
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Tim Boyce
Dispersion of Pigments
Pigment Powder
DecreasingParticle
size
Agglomerates
Aggregates
Primary Particles
Properties ofOrganic Pigments
Slide 173
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Tim Boyce
1. 1. DeagglomerationDeagglomeration -- premixing of single pigments to premixing of single pigments to break down larger, softer agglomerates. Initialbreak down larger, softer agglomerates. Initialwetting out.wetting out.
2. Dispersion2. Dispersiona) a) WettingWetting –– most important stepmost important step. Often requires use . Often requires use of auxiliaries to improve pigment wetting. of auxiliaries to improve pigment wetting. Solvent and resin should cover entire pigment Solvent and resin should cover entire pigment surface. Polar carriers and solvents have surface. Polar carriers and solvents have better wetting power.better wetting power.b) b) DispersionDispersion –– all pigment agglomerates are broken all pigment agglomerates are broken down. This is done by friction and pressure down. This is done by friction and pressure (shear forces).(shear forces).c) c) DistributionDistribution –– optimal statistical distribution of the optimal statistical distribution of the
dispersed pigment within the carrier materialdispersed pigment within the carrier materiald) d) StabilisationStabilisation –– protection of the system against protection of the system against
reagglomerationreagglomeration or flocculationor flocculation
Dispersion of organic pigments
Properties ofOrganic Pigments
Slide 174
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Tim Boyce
Step 1> 100 u
Step 250 - 100 u
Step 7< 1 u
Step 61 - 5 u
Step 55 - 10 u
Step 410 - 20 u
Step 320 -50 u
Microscopic DispersionEvaluationScale (x 110 times)
Properties ofOrganic Pigments
Slide 175
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Tim Boyce
Dispersion of pigments – relative particle size of some inorganic and organic pigments
Colour Index Pigment Type Particle Size (µm)Inorganic pigments
Pigment Black 7 Carbon black 0.01 – 1.0
Organic pigments
Pigment Yellow 180 Benzimidazolone 0.18
Pigment White 6 Titanium dioxide 0.1 – 1.0Pigment Yellow 34 / Pigment Red 104
Lead chromates / molybdates
0.5 – 1.0
Pigment Blue 29 Ultramarine blue 0.3 – 8.0
Pigment Yellow 13 Diarylide yellow 0.06
Pigment Orange 43 Perinone 0.15Pigment Red 254 Diketopyrrolopyrrole 0.2Pigment Violet 23 Dioxazine 0.06Pigment Blue 15:3 Β-phthalocyanine 0.09
Pigment Red 101 Iron oxide red 0.1 – 0.6
Properties ofOrganic Pigments
Slide 176
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Tim Boyce
Effects of FlocculationLoss of colour strengthPoor levelling (in paints)Poor flowReduced glossHazingShade variation
Flocculation
Properties ofOrganic Pigments
Slide 177
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Tim Boyce
0 min 25 min
40 min 60 min
90 min 120 min
Flocculation v’s time
Test system
CPP gravure ink5% pigment conc.
Magnification x 110
Properties ofOrganic Pigments
Slide 178
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Tim Boyce
particle size
moreopaque
lowstrength
lowvisc.
higherfastness
higherloading
lowSpecificSurface
Area
lower fastness
lowerloading
highSpecificSurface
Area
highvisc.
highstrength
moretrans.
trans
pare
ncy
/
opac
itytin
t
stre
ngth
visc
osity
(flow
)
spec
ific
Sur
face
are
a
millb
ase
conc
entra
tion
fast
ness
prop
ertie
s
large
small
Particle size & distribution – general rules
* these are guidelines only and other factors may need to be considered
Properties ofOrganic Pigments
Public
ASEAN Regional Technical ServicTim BoycePigment Technical Service Laboratory – ASEAN Region
Key fastness propertiesof organic pigments
MigrationHeat stabilityLightfastnessWeatherfastness
Public
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Migration fastnessof organic colourants
Solvent fastnessBleedingOversprayBlooming
Slide 181
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Tim Boyce
• Paint : This is tested on the pigment powder itself, using individual solvents or a solvent mixture.
• Ink : For offset ink, this is tested on the print application using either individual solvents or a solvent mixture.For gravure pigments it is tested on the individual pigments using either individual solvents or a solvent mixture.
•• evaluation is against the 5 step Grey Scale (DIN 54002)
The pigment is dissolved by the solvent, thereby discolouring the solvent
The pigment is dissolved by the solvent, thereby discolouring the solvent
Solvent fastness
Properties ofOrganic Pigments
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Toluene
IPA
Toluene/IPA(70/30)
GR200 P-GRL 06 DHG SPL MXSTD STD STD STDP.Y.12 P.Y.13 P.Y.12 P.Y.13
Solvent Fastness Test - tested on pigment powder
Solvent fastness
Properties ofOrganic Pigments
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Tim Boyce
Bleeding pigment moves from the colouredmaterial to directly contacting material
Overspraypigment moves into subsequentpaint layers thereby discolouring them
Bloomingpigment migrates to the surfaceand can be wiped off
Migration fastness
Properties ofOrganic Pigments
Public
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Bleeding / Blooming.
White contact film
Red coloured filmWhite paper covered with colour
Plaques with coloured dust on the surface.
► Incorrect pigment selection► Dyestuff used in partly crystalline polymers► Pigments soluble in the binder or polymer► Pigments soluble in the solvent or plasticiser► High processing temperatures / poor heat stability
Properties ofOrganic Pigments
Slide 185
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Tim Boyce
Migration fastness - bleeding
Retort fastness – 120’C / 30 minutes
Properties ofOrganic Pigments
Slide 186
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Tim Boyce
P.R.170 P.R.3
► Bleeding in an overspray application(tested in thermosetting acrylic)
Migration fastness - overspray
Properties ofOrganic Pigments
Slide 187
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Tim Boyce
Example of blooming inLow Density Polyethylene
Migration fastness - blooming
Properties ofOrganic Pigments
Slide 188
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Tim Boyce
Recrystallisation due to poor solvent fastnessin aromatic solvents (tested in medium oil alkyd)
Aromatic solvents or high heat (above 200’C) cause a crystal shift resulting in a greener, weaker product
Non flocculating version ofPigment Blue 15:1 i.e.it is a non-recrystallising or flocculatinggrade
Control 1 week aged Control 1 week aged
Pigment Blue 15:0 Pigment Blue 15:2
Solvent fastness - Recrystallisation
Properties ofOrganic Pigments
Public
ASEAN Regional Technical ServicTim BoycePigment Technical Service Laboratory – ASEAN Region
Heat stability /Limit concentration
Slide 190
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Pigment is either discoloured or destroyed depending on the conditions and / or the nature of the pigment
Properties ofOrganic Pigments
Heat stability
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Tim Boyce
Pigment is “burnt out” in polypropylene polymer and colour “disappears”
Heat stability
Initial matching designed for applicationat 240’C maximum
Final colour when processed at280’C
Properties ofOrganic Pigments
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Tim Boyce
Heat stability - 0.5% pigment, 5 minute dwell timePigment discolours
Heat stability
Properties ofOrganic Pigments
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Tim Boyce
Heat resistance (DIN EN 12877)Heat resistance test
Properties ofOrganic Pigments
Public
ASEAN Regional Technical ServicTim BoycePigment Technical Service Laboratory – ASEAN Region
Lightfastness –resistance to UV radiation
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Tim Boyce
Is a measure of the resistance to UV radiation ONLY i.e. It is not a measure of exterior durability
Can be accelerated or actual exposure under glassEvaluated against the Blue Wool Scale according to
DIN EN ISO 105-BO 2Blue Wool Scale must be exposed at same time
as sample and result must specify timeand conditions
Blue Wool Scale is geometric - each successivestep is twice the previous step
Limited rating system of 1 (very poor) to 8 (very good)Final lightfastness is system dependent
Lightfastness
Properties ofOrganic Pigments
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Tim Boyce
Global radiation in Kly (DIN EN ISO 4892)
70
70
70
70
60 60
60
8080
80
80 100
100
100100
100
120120
120
120
120120
140
140 140
160
160160160
160 160
160-180
180180180
180
160
200
Properties ofOrganic Pigments
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Tim Boyce
160160
170
170
180
180190
190
200
200
160160
150150
140140
160150140
130
120
160
150140
130
120
Kilolangleys/year of radiation in Australia
Lightfastness – variation in radiation levels
Properties ofOrganic Pigments
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Tim Boyce
1 Langley = 1 cal/cm2 = 4,188 J/cm2
1 W/m2 = 0,0001 W/cm2
1 Luxh = 0,581 x 10-3 cal/cm2 = 0,581 x 10-3 Ly = 2,433 x 10-3 J/cm2
1 J/cm2 = 10 KJ/m2 = 0,2388 Ly = 411 Luxh
1 Lux = 0,161 x 10-6 cal/(cm2 x s) = 0,676 x 10-6 W/cm2
Conversion Table
1 Langley = 4,18 Joule/cm2
= 4,18 Ws/cm2
= 1,00 cal/cm2
The light energy of 1 year in Frankfurt is approximately 80 Kly = 3350 MJ/m2
Properties ofOrganic Pigments
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Tim Boyce
Lightfastness – Blue Wool Scale
Step 1
Step 8
Step 2
Step 3
Step 4
Step 5
Step 6
Step 7
Exposed section250 hours
Rating
4 – 5
6
8
Properties ofOrganic Pigments
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Tim Boyce
Properties ofOrganic Pigments
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Types of Accelerated UV/Weathering Apparatus
Properties ofOrganic Pigments
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Tim Boyce
3. Light fastness (DIN EN ISO 4892)Different types of exposure
Blue wool scale
Accelerated exposure* in hours
(in Xenotest X 1200 W)
Normal daylight exposure* in days
(in Frankfurt-Liederbach Germany)
1 6 h 5 days
2 10 h 10 days
3 25 h 20 days
4 120 h 40 days
5 200 h 80 days
6 400 h 160 days
7 800 h 350 days
8 1.600 h 700 days (16.800 hours)
*test with a glass filter / behind glass
Properties ofOrganic Pigments
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Tim Boyce
Light fastness (DIN EN ISO 4892)Comparison of various accelerated exposures
Blue Wool Scale
Normal daylight
exposure in days *
Accelerated exposure in
hours in XenotestX 1200 W
Accelerated exposure in
hours in Xenotest XE
1200 GL
Accelerated exposure in
hours in Weathero-
meter
Accelerated exposure in
hours in Suntest
2.5 hrs 2.5 hrs
6.5 hrs
9 hrs
41 hrs
80 hrs
130 hrs
260 hrs
520 hrs
8 hrs
20 hrs
75 hrs
160 hrs
270 hrs
540 hrs
1100 hrs
2.5 hrs
6.5 hrs
15 hrs
60 hrs
110 hrs
200 hrs
400 hrs
800 hrs
1 4 days 5.4 hrs
2 14 days 15 hrs
3 28 days 34 hrs
4 70 days 100 hrs
5 100 days 240 hrs
6 140 days 400 hrs
7 160 days 800 hrs
8 360 days 1600 hrs
Note : The time for outdoor exposure of stages 1 – 7 is very dependent on thetime of year at which the test began.
* The outdoor exposure test is tested behind window glass
Properties ofOrganic Pigments
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Tim Boyce
Blue wool scale
Exposure time Xenotest X 1200 W
Exposure in daylight in days (in Liederbach)
Dyestuff
1 6 h 5 Acilan Br. Blue FRR (Bayer)
2 15 h 10 Acilan Br. Blue FFB (Bayer)
3 34 h 20 Sypranolcyanine 6B (Bayer Bencylcyanine (Ciba)
4 120 h 40 Supramin Blue EG (Bayer)
5 240 h 80 Solmay Blue RN (ICI) Acilan Fast Blue RX (Bayer)
6 400 h 160 Alicarin Lightblue 4GL (Clariant)
7 800 h 350 Soledon Blue 4BC (ICI) Indigosol Blue 04B (Durand) Anthrasol Blue 04B (DyStar)
8 1.600 h 700 Indigosol Blue AGG (DyStar)
Dyes used in Blue Wool Scale
Properties ofOrganic Pigments
Public
ASEAN Regional Technical ServicTim BoycePigment Technical Service Laboratory – ASEAN Region
Resistance to Weathering
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Tim Boyce
It is a measure of all exposure conditionse.g. UV, rain, snow, industrial atmosphere etc
Can be accelerated e.or actual exposuree.g. Florida or Allunga, Xenotest or QUV
Evaluated against the Grey Scale and/or bycolour difference measurement
Carried out as per DIN 54001
Results can be different to lightfastness
Results are highly system dependent
Properties ofOrganic Pigments
Weatherfastness
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Tim Boyce
Global Climate Classification (Koeppen)
Properties ofOrganic Pigments
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Tim Boyce
Primary effectsSolar radiation (light energy)Temperature and temperature differencesWater (moisture)
Secondary effectsAirborne pollutantsAcid rainBiological effects (mold, mildew)
Weatherfastness factors
Primary + Secondary effects
Weathering
Properties ofOrganic Pigments
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Tim Boyce
The result is unwanted and premature product failures
This could mean:
Effects of weathering
Discoloration
Cracking Peeling Paint
Rust
Properties ofOrganic Pigments
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Tim Boyce
The weather fastness properties of a colorant are a feature of molecular structure and particle size. Many factors, most importantly polymer stabilization, pigment concentration and thestrength of UV radiation can influence the result. Accelerated weathering in a weather-o-meter can provide a good indication of the performance of a given formulation however, a pre-test under the applied conditions of use is always recommended.Visual evaluation with the 5-step grey scale for assessing change in color in accordance with ISO 105-A02 : 1993→ 5 = very good; 1 = very bad
The test can be run until Stage 3 of the Grey Scale is reached. The hours of the exposure or the energy values (Kly) can be recorded and compared. Alternatively a fixed exposure time e.g. 3000 hours can be used and results rated on the Grey Scale
Properties ofOrganic Pigments
Fastness to weathering (accelerated ageing, DIN EN ISO 4892)
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Tim Boyce
Fastness to weathering Test machine: accelerated weathering (DIN EN ISO 4892)
Machine Energy (1 h)
Xenotest 1200 W (rotating panel) 1,764 MJ/m2
Relative Humidity 60 % Black Panel = 60 °C
1 Langley = 4,18 Joule/cm2
= 4,18 Ws/cm2
= 1,00 cal/cm2
The light energy of 1 year inFrankfurt is 80 Kly = 3350 MJ/m2
Accelerated test cyclesEurope South East Asia
Wet Dry Wet Dry18 mins 102 mins 240 mins 240 mins
Properties ofOrganic Pigments
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Tim Boyce
. Fastness to weathering ISO 105-A02: 1993Grey scale for assessing change in color
Properties ofOrganic Pigments
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Tim Boyce
Fastness to weathering Summary (DIN EN ISO 4892)
It is a total system test, where all components and exposure conditions must be taken into account- polymer/binder type and stabilization- pigment type and concentration- UV radiation, temperature, moisture etc
The important criteria is how long the final article is in actual outdoor use and where it is placed –locally and in the world (Global radiation and climate conditions vary considerably)
Testing should be carried out as per the final pigment formulation in the defined polymer/binder system, including stabilization
Properties ofOrganic Pigments
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Tim Boyce
Various fastness properties depend on :
• Entire system e.g. resin,additives,pigments,fillers• Pigment concentration / film thickness• Pigment type (chemical constitution)• Shade depth / pigment mixtures• Temperature• Time• Nature of process e.g. dispersion method, solvents
Parameters affecting fastness properties – general rules
Properties ofOrganic Pigments
Public
ASEAN Regional Technical ServicCorporate Presentation
Quality Aspects
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Tim Boyce
Reference standards
* Exist for all sales products* Represent average production quality* Tested together with each production batch* Used in all decisions regarding quality* For new standards - everyone is notified* Customers must be notified* Sample stock is held for customers
Quality aspects
Quality aspects
You should know that ……
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Tim Boyce
Volatile matter (moisture)Sieve residuepH valueSpecific conductivitySolvent fastnessViscositySpecific gravity
ColourStrengthOpacity / TransparencyGlossDispersibilityMigration fastness RheologySpecific customer tests
Pigment / Preparation
Application
Quality aspectsWhat do we standardise ?
Quality aspects
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Tim Boyce
• Description of test conditions :• type of binder• dispersion method and conditions• application• evaluation criteria
• Test methods based on :• DIN or ISO or ASTM Standards• specific requirements
Test methods
Quality aspects
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Tim Boyce
dH (Hue)
Adjustment of shade depth :• relative tinctorial strength (+/- 5% or 105%)• residual dH, dC, dL, and dE (at dL = 0)• “ d ” means difference against standard
Note : only used with reduced shade
CIElab system
dL (Lightness)
dC (Chroma)
Colour measurement
Quality aspects
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Tim Boyce
Colour measurement
greenish yellow
yellowish green
greenish blue reddish blue
reddish yellow
bluish redbluish green
yellowish red
CIElab - System DIN 6174
Greenish yellow
Yellowish green
Bluish red
Reddish blue
Bluish green
Greenish blue
Yellow
Red
Blue
Green
Reddish yellow
Yellowish red
Quality aspects
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Tim Boyce
CIElab System
- dH + Tolerances
dC dH/=/ Equal 0.00 – 0.10 0.00 – 0.10
1 Trace 0.11 – 0.30 0.11 – 0.20
2 Slightly 0.31 – 0.80 0.21 – 0.50
3 Noticeably 0.81 – 1.40 0.51 – 0.80
4 Distinctly 1.40 – 2.20 0.81 – 1.40
5 Considerably 2.21 – 3.00 1.41 – 2.00
6 substantially > 3.01 > 2.00
Chroma & Lightnessgreener Blue redder
Lighter + dL - Darker+ dC -yellower Green Dullerbluer Brighter
bluer Violet redder
bluer Red yellower
redder Orange yellower
redder Yellow greener
Colour measurement
Quality aspects
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Tim Boyce
Up to 6% Up to 11% Up to ?? %
Total cost
Planning
Auditing
Training
Quality Assurance
PreventionDesign
Inspection
Test equipment
Evaluation
Record Storage
Replacement
Rework
Repair
Re-inspection
Downtime
Scrap
Diagnosis
FailureAppraisal
Quality costs
Quality aspects
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Tim Boyce
We need : - Sample and lot number of pigment ex delivery- Customer’s evaluation- ALL details of customer’s test method and
application- Method of processing
We check :Method of standardisation + customer’s application method
Technical decision Additional information
Commercial decision
Technical & Quality complaint procedures
Quality aspects
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Tim Boyce
• Product Reports : specific, new release, deletions, changes….
• Pattern cards : specific applications, sales range, product information & illustration,
fastness properties
• Technical specifications : QC, product quality, fastness properties
• Certificates of analysis : certification, test results,
• Safety data sheets : chemistry, safety, transport, toxicology, ecology, accidents, health
Literature & information
• It is important that these are up to date• It is important that the information is clearly understood
Quality aspects
Public
ASEAN Regional Technical ServicCorporate Presentation
Clariant Product Range
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Tim Boyce
Hostaperm Highest Quality
Novoperm Very High Quality
Permanent Very Good / Good quality
Hansa Specific Range with very good specific properties
Reflex Blue Specific Range
PV Fast Highest quality selectively tested for plastics
Graphtol Very Good / Good quality selectively tested for plastics
Clariant product ranges –Pigments
Clariant ProductRange
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Tim Boyce
Savinyls range of solvent dyes
Solvaperm range of solvent dyes for plastics
Polysynthren range of solvent dyes for plastics
Fat range of solvent dyes
Hostasols range of fluorescent solvent dyes for plastics
Duasyn range of water soluble dyes
Vitasyn range of water soluble food dyes
Cartasol range of water soluble dyes
others range of water soluble dyes
Clariant product ranges –Dyestuffs
Clariant ProductRange
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Tim Boyce
Colourants
Pigment
powdergranulespresscake
Dyestuff
powderliquid
Preparation
powderpastefine granulesgranulesflush pastes
Clariant product ranges –Supply forms
Clariant ProductRange
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Standard Range
Properties Chemistry
QuinacridonePhthalocyanineDioxazineBenzimidazoloneDibromoanthranthrone
Naphtol AS
Diarylide
BenzimdazoloneNovoperm Very good fastness
Naphtol ASPermanent Average to good fastness. High colourstrength
Hostaperm Excellent fastness properties
Clariant product ranges –Pigments
Clariant ProductRange
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Tim Boyce
Most commonly used in High Quality applications such as :
• Automotive Paints (OEM & Refinish)
• High quality industrial paints
• Decorative paints (where light and weatherfastness are critical)
• Inks (where high fastness properties are required - metal dec)
Clariant ProductRange
Hostaperm
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Tim Boyce
Most commonly used in High Quality applications such as :
• Automotive paints (mainly Refinish)
• High quality industrial paints
• Decorative paints (where light and weatherfastnessare critical)
• Inks (where high fastness properties are required - metal dec)
Clariant ProductRange
Novoperm
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Tim Boyce
These grades are most commonly used in ink applications although a number are suitable for paint applications (mainly reds) :
• Offset inks (Sheetfed, Heatset, Coldset)
• Solvent & water based liquid inks (Gravure, Flexo)
• General industrial paints
• Decorative paints
Permanent
Clariant ProductRange
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Standard Range
Properties Chemistry
MonoazoHansa Good fastness to light but poor solvent fastness Beta naphtol
Reflex Blue
Low fastness. High colour strength
Triphenylmethane
PV Fast High thermal stability and fastness
Selected Hostaperm and Novoperm grades
Graphtol Moderate thermal stability and fair to good fastness
Selected Novoperm and Permanent grades
Clariant product ranges –Pigments (continued)
Clariant ProductRange
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Tim Boyce
These grades are most commonly used in decorative paint applications although a some are used in ink applications.
They are sensitive to strong solvents e.g.aromatics
• Screen inks
• Solvent & water based liquid inks (gravure, flexo)
• General industrial paints
• Decorative paints
Hansa
Clariant ProductRange
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Tim Boyce
These grades are almost exclusively used in offset ink applications although some are used in other ink
applications or special fields. They are sensitive to strong solvents e.g.aromatics
• Offset inks (Sheetfed, Heatset, Coldset)
• Water based flexo inks (Powder grades only)
• Special applications (carbon paper etc)
Permanent
Clariant ProductRange
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Tim Boyce
These grades are primarily used for plastics applications. Selected pigments are from Hostaperm, Novoperm and Permanent ranges with all grades standardised in PVC
• Polyolefines & PVC
• Elastomers
• Engineering resins
• Powder coatings
PV Fast & Graphtol
Clariant ProductRange
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Tim Boyce
Clariant product ranges –Dyestuffs
Standard range Application field Properties
Hostasol Plastics Fluorescent
Solvaperm Plastics Good fastness
Polysynthren Higher performance plastics
High fastness
Fat Solvent systems, waxes
Multiple applications
Duasyn Special applications Multiple applications
Vitasyn Foodstuffs, cosmetics Registered products
Savinyl Ink, coatings, Special applications
Multiple applications
Clariant ProductRange
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Tim Boyce
Paint Printing Ink Plastics Specialised
Colanyl 100 Traditional Hostaprint Flexonyl
Colanyl 500 Flexonyl WF Hostasin Viscofil
Hostatint Flexonyl A Viscofil A
Hostatint E NIP Viscofil S
Hostatint A Permajet liquid
Cosmenyl
Hostafine Permajet 30 Cosmenyl gran.
Renol HW Hostajet
Hostacopy
Clariant product ranges –Preparations
Clariant ProductRange
Public
ASEAN Regional Technical ServicTim BoycePigment Technical Service Laboratory – ASEAN Region
Product safety
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Tim Boyce
Product Safety
Prior to marketing a product all legal requirements must be fulfilled!
Worldwide Chemical Legislation- Chemical Registration- Quantity Monitoring- Classification and Labeling of hazardous substances and
preparations
Transport Classification
Special Regulations- Chemical Prohibition Ordinance- Consumer Goods Ordinance- Positive/Negative Lists
REACH
Mandatory Regulations:
Product safety
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Tim Boyce
International Environmental LabelsUSA: Green SealJapan: Eco MarkScandinavia: White SwanCanada: Environmental ChoiceGermany: Blue AngelEurope: Flower
EU-Eco-Labels- Textile products- Footwear- Bed mattresses- Indoor paints- Bed linen and T-shirts- Copy paper
Internal StandardsDIN EN ISO 9001DIN EN ISO 14001
Voluntary Regulations:
Product Safety
Product safety
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Tim Boyce
In Force In Preparation European Union Switzerland USA Canada Australia Japan New Zealand Philippines South Korea China (partly) Czech Republic (partly) Hungary (partly) Poland (partly)
Eastern Europe Russia, Baltic States, Bulgaria, Romania, Slowenia, Slovac Republic
Mexico Malaysia Singapore Taiwan Thailand South Africa
Worldwide Chemical Legislation
Product safety
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Tim Boyce
Chemical Legislation Inventories
EINECS European Inventory of Existing Commercial Substances
REACH Registration, Evaluation, Authorisation and Restriction of Chemicals
USA TSCA Toxic Substances Control Act
Canada DSL Domestic Substances List
Japan ENCS Japanese Existing and New Chemical Substances
Australia AICS Australian Inventory of Chemical Substances
Korea ECL Existing Chemicals List
Philippines PICCS Philippines Inventory of Chemicals and Chemical Substances
China ECSC Inventory of Existing Chemical Substances in China
EU
Product safety
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Tim Boyce
Austrian Approval (AT)ASTM: Safety of Toys (US)BfR Requirements (G)CONEG-Regulation (US)Consumer Goods Ordinance (G)Chemical Prohibition (G)EU-Resolution AP (89) I (EU)EU-Toys Standard EN 71/3 (EU)EU-Preparations Directive 1999/45/ECFDA-Approval (US)French Positive List (FR)JHOSPA (JP)JHPA (JP)REACHStandard 2070.6 (AU)
Major worldwide regulations affecting pigments
Product safety
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Tim Boyce
PurityMigration fastnessToxicological properties
For colorants that are used for coloring consumer goods, food packaging and toys the parameters relating to
are of essential importance.
With these criteria the risk evaluation of colorants serves as the basis for the suitability of the colorants for specific areas of application.
Colorants for the coloration of consumer goods, food packaging and
toys
Product safety
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Tim Boyce
Recommendation IX of BfR (former BgVV)
Purity criteria for colorants for the coloration of plastic materials and other polymers for consumer goods- Heavy metal limits- Limit for primary aromatic amines
Heavy metal limitsThe following limiting values must not be exceeded (extractable in 0.1 N HCl)
As 100 ppmBa 100 ppmCd 100 ppmCr 1000 ppm
Hg 50 ppmPb 100 ppmSb 500 ppmSe 100 ppm
Colorants for the coloration of consumer goods, food packaging and
toys
Product safety
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Tim Boyce
European Resolution AP (89) I"On the use of colorants in plastic materials coming into contact with food"
Purity criteria for colorants- Heavy metal limits- Limit for primary aromatic amines- Limit for polychlorinated biphenyls (PCB)Heavy metal limitsThe following limiting values must not be exceeded (extractable in 0.1 N HCl)
Primary aromatic aminesThe content of unsulphonated primary aromatic amines soluble in 1N HCl should not exceed 500 ppm (calculated as aniline)The content of sulphonated aromatic amines should not exceed 500 ppm (calculated as aniline sulphonic acid)The content of benzidine, ß-naphthylamine and 4-aminobiphenyl, singly or in total, should not exceed 10 ppm2-methyl-4-chloroaniline should be treated in the same wayThe content of polychlorinated biphenyls (PCB) should not exceed 25 ppm
As 100 ppmBa 100 ppmCd 100 ppmCr 1000 ppm
Hg 50 ppmPb 100 ppmSb 500 ppmSe 100 ppm
Colorants for the coloration of consumer goods, food packaging and toys
Product safety
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Tim Boyce
Heavy metal limits (ppm*) for colorants in food packaging –Country overview
Country/Metal As Ba Cd Cr Hg Pb Sb Se Zn Australia 100 100 100 1000 50 100 500 100 Belgium 100 100 100 1000 50 100 500 100 Germany (Rec. IX) 100 100 100 1000 50 100 500 100 EU/AP (89) I 100 100 100 1000 50 100 500 100 France 100 100 100 1000 50 100 500 100 Great Britain 100 100 100 1000 50 100 500 100 Greece 100 100 100 1000 50 100 500 100 Italy 50 100 100 1000 50 100 500 100 Japan (JHPA)** 50 100 50 100 Japan (JHOSPA) 50** 100 100** 1000 50** 100* 250 100 Netherlands 100 100 1000 1000 50 100 2000 100 Portugal 100 100 100 1000 50 100 500 100 2000 Switzerland 100 100 100 1000 50 100 500 100
* Soluble contents in diluted HCl ** Total content
Colorants for the coloration of consumer goods, food packaging and
toys
Product safety
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Heavy metal limit values for toys (ppm) - Country overview
Country/Metal As Ba Cd Cr Hg Ni Pb Sb Se Sr Australia (toy coatings) 25 500 75 60 60 90 60 500 Australia (modeling clay,
finger paints) 25 250 50 25 25 90 60 500
Australia (total content in modeling compounds)
1,0 1,0 0,05 1,0 0,03 1,0 1,5 1,5 1,0 1,0
EU EN 71/3 Tab. 1 (surface coatings etc.)
25 1000 75 60 60 90 60 500
EU EN 71/3 Tab. 2 (modeling clay) 25 250 50 25 25 90 60 500 EU EN 71/7 (finger paints) 10 350 15 25 10 25 10 50 United Kingdom (coatings of
pencils, pens, etc.)
100 1000 100 100 [Cr(VI)]
100 250 250
Switzerland (Art. 31) (coatings of paints, drawing etc.)
25 1000 75 60 60 90 60
Switzerland (Art. 32) (water colors) 25 1000 75 60 60 90 60 USA ASTM F 963-96a (surface coatings) 25 1000 75 60 60 90 60 500
Colorants for the coloration of consumer goods, food packaging and
toys
Product safety
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Purity of our products
Colorants for the coloration of consumer goods, food packaging and
toys
Antimony 60 ppm (EN 71-3)Arsenic 25 ppmBarium 100 ppmCadmium 50 ppmChromium 60 ppmLead 90 ppm (EN 71-3)Mercury 25 ppmSelenium 100 ppmZinc 1000 ppm
Primary aromatic amines 500 ppm*
4-aminobiphenyl, benzidine2-naphthylamine, 2-methyl-4-chloroaniline 10 ppm
* = calculated as aniline
Products which are subject to regular analytical tests meet the following purity criteria:
The maximum soluble content (in 0.1 N respect. 1N HCl) of the following elements is:
Product safety
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Tim Boyce
Migration fastness
Colorants for the coloration of consumer goods, food packaging and
toys
For the suitability of colorants for the coloration of food packaging, consumer goods and toys lowest possible migration from the colored article onto the food is of essential importance.The migration is among others dependent upon
the properties of the packaging material usedthe type and quantity of other additives (and their possible interaction with the colorant) contained in the packaging material such as anti-oxidizing agents etc.the concentration and the properties of the colorantsthe application procedurethe food and the storage conditions
Product safety
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Tim Boyce
Toxicological Properties
Important toxicological tests for pigments are:
acute toxicityirritation of skin and mucous membranetoxicity after repeated applicationsensitizationmutagenicitychronic toxicity, especially carcinogenicity
The most important property of organic pigments is their extremeinsolubility in water and the application media.
Colorants for the coloration of consumer goods, food packaging and
toys
Product safety
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Organic Pigments -The Basics
Tim Boyce
The Issue of HCB (hexachlorobenzene) and TCPA (tetrachlorophthalicanhydride)A) IntroductionOn February 24, 2006 the Japanese Authorities published an official letter announcing the prohibition of the use of Tetra Chloro Phthalic Anhydride (TCPA) due to its contamination with Hexachlorobenzene(HCB). Additionally the industry has been asked to stop using TCPA and also to stop the distribution of products made from TCPA
In Japan HCB is a Class I specified substance under the ChemicalSubstances Control Law. In the scope of this law the production, import and usage of HCB is prohibited.
Moreover HCB belongs to the "dirty dozen" which have been prohibited in the scope of the international POP’s convention.
The authorities have identified Solvent Red 135 as a colorant containing HCB impurities due the manufacturing process using TCPA.
No official limit with regard to trace impurities of HCB in colorants has been published yet.
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B) Actions taken by the industry for the time being
Because of the complexity of the whole matter a task force of the Japanese industry has been formed to develop a common strategy.
As an initial step the authorities have been informed that also other colorants than those based on TCPA may contain HCB impurities.
The HCB content of a colorant is related to the raw materials and solvents used for the production and the production process. The first step is to define voluntary HCB limits for the individual colorants and to harmonize the limits with the authorities followed by a stepwise reduction of the impurity levels.
The Issue of HCB (hexachlorobenzene) and TCPA (tetrachlorophthalicanhydride)
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C) Clariant products affected
We generally do not use any HCB for the manufacturing of our colorants.
1. TCPA based colorants within our range are Solvent Red 135 (Solvaperm Red G / Polysynthren Red GFP) Pigment Red 257 (Hostaperm Red Violet 3RL)
2. Other colorants of concernPigment Green 7 (e.g. PV Fast Green GNX / Hostaperm Green GNX)
The Issue of HCB (hexachlorobenzene) and TCPA (tetrachlorophthalicanhydride)
Note : this is an issue in Japan only and currently does not have relevance in any other country
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Chlorine Free Pigments for Plastics
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Chlorine free pigments/dyes (less than 1% chlorine)Pigment Colour Index Chemical classification
Graphtol Yellow 3GP P.Y.155 Bisacetoacetarylide
Benzimidazolone
Benzimidazolone
Benzimidazolone
Isoindolinone
Benzimidazolone
Perinone
Naphtol
Naphtol
Naphtol
Monoazo
Benzimidazolone
Benzimidazolone
β Quinacridone
β Quinacridone
Benzimidazolone
Benzimidazolone
PV Fast Yellow H2G P.Y.120
PV Fast Yellow HG 01 P.Y.180
PV Fast Yellow HG P.Y.180
Graphtol Yellow H2R P.Y.139
PV Fast Yellow H3R P.Y.181
PV Fast Orange GRL P.O.43
PV Fast Red HB P.R.247
Graphtol Red F3RK 70 P.R.170
Graphtol Red F5RK P.R.170
Graphtol Rubine 6BP P.R.57:1
PV Fast Red HFT P.R.175
Graphtol Red HF2B P.R.208
PV Fast Red E3B P.V.19
PV Fast Red E5B P.V.19
Graphtol Carmine HF3C P.R.176
Graphtol Carmine HF4C P.R.185
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Chlorine free pigments/dyes (less than 1% chlorine)Pigment Colour Index Chemical classification
PV Fast Pink E P.R.122 Dimethyl Quinacridone
Dimethyl Quinacridone
Benzimidazolone
γ Quinacridone
α Phthalocyanine
β Phthalocyanine
Chemical classification
Quinoline
Methine
Anthraquinone
Perinone
Perinone
Monoazo
PV Fast Pink E 01 P.R.122
Graphtol Bordeaux HF3R P.V.32
PV Fast Violet ER P.V.19
Graphtol Blue AN P.B.15:0
PV Fast Blue BG P.B.15:3
Dyes Colour Index
Sandoplast Yellow 2G S.Y.114
Polysynthren Yellow GG S.Y.133
Polysynthren Yellow NG P.Y.147
Sandoplast Orange 3G S.O.60
Sandoplast Red 2G S.R.179
Sandoplast Red BB S.R.195
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FDA Compliant Colorants from Clariant
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1. General remarksThe Food and Drug Administration (FDA) regulates cosmetics, medical devices, drugs (including food additives and food packaging) in the United States.FDA regulations are compiled in Title 21 of the Code of Federal Regulations(21 CFR). These regulations can be amended in the Federal Register, or as described below.
FDA regulations are organised in Parts.The parts that are most relevant to food contact are :> Part 175 – Adhesives and Coatings> Part 176 – Paper and Paperboard> Part 177 – Polymers> Part 178 –Adjuvants, Production Aids, Sanitisers> Part 181 – Prior Sanctions> Part 184 – Affirmed GRAS Substances> Part 186 – Food Contact Substances Affirmed as GRAS
Detailed regulatory information is found in paragraphs such as § 178.3297, Colorants for Polymers
FDA ApprovalSummary of the regulations concerning food packaging
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2. Legal and Regulatory Background – FDA Compliance for Food AdditivesA food additive is a substance which, when used as intended, is reasonably expected to become a component of food. Afood additive must be already regulated, exempt or precleared.
Three types of food additives are recognised :> Direct (food ingredients)> Secondary Direct (added to food during processing but removed)> Indirect (food packaging and other food contact)
An indirect food additive, also called a food contact substance, is any substance intended for use as a component of materials used in manufacturing, packaging, transporting orHolding food. Such use is not intended to have a technical effect in food.Food contact substances must also be already regulated, exempt or precleared. However, food contact substances are likely to have exemptions or preclearances.
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2.1 Regulated Colorants for Polymers2.1.1 21 CFR, § 178.3297, Colorants for Polymers
Colorants for polymers are listed in 21 CFR § 178.3297, Colorants for Polymers.The colorants are listed with their chemical names and/or with their Colour Index generic Names. Many of the colorants are subject to restrictions on :
> Upper limit colour concentrations in the polymer> Polymer types> Food types (aqueous, acidic, fatty, low alcohol, high alcohol) and/or> Conditions of use
Conditions of use describe the temperature conditions the coloured polymer may be subjectto and are described as follows :
A – High temperature heat sterilised e.g. > 100’C / 212’ FB – Boiling water sterilisedC – Hot filled or pasteurised above 66’C ( 150’ F)D – Hot filled or pasteurised below 68’C (150’ F)E – Room temperature filled and stored (no thermal treatment in the container)F – Refrigerated storage (no thermal treatment in the container)G – Frozen storage (no thermal treatment in the container)H – Frozen or refrigerated storage : ready prepared foods intended to be reheated in
the container at time of use
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2.1 Regulated Colorants for Polymers2.1.2 Food contact Notifications
As of January, 2000, the FDA no longer lists cleared substances in 21 CFR § 178.3297.Rather, substances cleared by the FDA as food contact substances will be listed on theFDA webpage. For a complete listing of FDA cleared substances, both 21 CFR § 178.3297and the FDA webpage must be researched.
The same restrictions as are found in 21 CFR § 178.3297 would be utilised in substances cleared by food contact notifications. It is important to note that only thecompany who is listed with the cleared substance on the FDA webpage may declaretheir product as FDA compliantProduct safety
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PY214PV Fast Yellow
H9G
PB15:1PV Fast Blue A4R
PG7PV Fast Green
GNX
PV19PV Fast Violet
ER
PR122PV Fast Pink
E 01
PR122PVFast Pink
E
PV19PV Fast Red
E5B
PV19PV Fast Red
E3B
PR187PV Fast Red
HF4B
PY254PV Fast Red
D3G
PY242PV Fast Scarlet
4RF
PY181PV Fast Yellow
H3R
PY191PV Fast Yellow
HGR
PY191PV Fast Yellow
H2GR
PY180PV Fast Yellow
HG
PR122DrizPearl Pink
E
PV19DrizPearl Red
E5B
PY181DrizPearl Yellow
H3R
PY180DrizPearl Yellow
HG
PB15:0Graphtol Blue
AN
PB15:3PV Fast Blue
BG
PB15:1PV Fast Blue A2R
Powder pigments
DrizPearls
FDA Compliant Products(coloration at SD1/3 + 1% TiO2)
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FDA Compliant Colorants with prescribed limitations
Product Colour Index Polymer % upper concentration Conditions of Use 21 CFR176.170 Food types
DrizPearl Yellow HG P.Y.180 All 1 B – G All foods
DrizPearl Yellow H3R P.Y.181 All 1 B – H All foods
DrizPearl Red E5B P.V.19 All 1 A – H All foods
1 D – G Aqueous, acidic,low alcohol
0.5 D – G
0.2 A - H
Graphtol Blue AN P.B.15:0 FDA compliant colour without limitation in 21 CFR 178.3297
PV Fast Yellow H9G P.Y.214 All 1 A – H All foods
PV Fast Yellow HG P.Y.180 All 1 B - G All foods
PV Fast Red E5B P.V.19 FDA compliant colour without limitation in 21 CFR 178.3297
1 D – G Aqueous, acidic,low alcohol
PV Fast Yellow H2GR P.Y.181 All 1 B - H All foods
PV Fast Red HF4B P.R.187 All 1 B – H All foods
PV Fast Red E3B P.V.19 FDA compliant colour without limitation in 21 CFR 178.3297
PV Fast Yellow HGR P.Y.191 All 1 B – H All foods
PV Fast Yellow H3R P.Y.181 All 1 B – H All foods
PV Fast Scarlet 4RF P.R.242 All 2 Maximum thickness 2 mm A - H Aqueous, acidic,low alcohol
PV Fast Red D3G P.R.254 All 1 B – h All foods
0.5 D – G Fatty foods
0.2 A - H All foods
1 D – G Aqueous, acidic,low alcohol
0.5 D – G Fatty foods
0.2 A - H All foods
PV Fast Violet ER P.V.19 FDA compliant colour without limitation in 21 CFR 178.3297
PV Fast Blue A4R P.B.15:1 FDA compliant colour without limitation in 21 CFR 178.3297
PV Fast Blue A2R P.B.15:1 FDA compliant colour without limitation in 21 CFR 178.3297
PV Fast Blue BG P.B.15:3 FDA compliant colour without limitation in 21 CFR 178.3297
PV Fast Green GNX P.G.7 FDA compliant colour without limitation in 21 CFR 178.3297
PV Fast Pink E 01 P.R.122 All
PV Fast Pink E P.R.122 All
DrizPearl Pink E P.R.122 All
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SBr53Polysynthren Brown
R
DY164Solvaperm Yellow
G
PY147Polysynthren Yellow
NG
PY151Hostaperm Yellow
H4G
SY133Polysynthren Yellow
GG
Colorants in PET
Optical Brighteners
LeucopureEGM
Hosta;uxKS 1
HostaluxKS
SG28Sandoplast Green
G
SB104Solvaperm Blue
2B
SB104Polysynthren Blue
RBL
SR195Solvaperm Red
BB
SR135Solvaperm Red
G
SR135Polysynthren Red
GFP
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FDA Compliant Colorants with prescribed limitations
Product Colour Index Polymer % upper concentration Conditions of Use 21 CFR176.170 Food types
Polysynthren Red GFP S.R.135 PET
High alcohol, fatty foods
0.2 E – F – G Aqueous, acidic,low alcohol
0.05 D – E – F – G All foods
Hostalux KS 1 N/A All
OlefineLeucopure EGM FB238
Hostaperm Yellow H4G P.Y.151 PET 0.01 E – F – G Aqueous, acidic,low alcohol
Polysynthren Yellow GG S.Y.133 PET 0.2 E - F - G Aqueous, acidic,low alcohol
0.25 E – F – G All foods
0.25 D – E – F - G Food types III, IV-A, VI
0.2 E – F - G Aqueous, acidic,low alcohol
Aqueous, acidic,low alcohol0.045 C – D
Polysynthren Blue RBL S.B.104 PET 0.2 E – F – G Aqueous, acidic,low alcohol
Polysynthren Brown R S.Br.53 PET 0.2 E – F – G Aqueous, acidic,low alcohol
PVCHostalux KS N/A
0.03 D – E – F – G All foods
Solvent Yellow G D.Y.64 PET 0.2 E – F – G Aqueous, acidic,low alcohol
Solvaperm Blue 2B S.B.104 PET 0.2 E – F – G Aqueous, acidic,low alcohol
Sandoplast Green G S.G.28 PET
0.2 E – F – G Aqueous, acidic,low alcohol
Aqueous, acidic,low alcohol0.045 C – D
High alcohol, fatty foods
Solvaperm Red BB S.R.135 PET 0.2 E – F – G Aqueous, acidic,low alcohol
All
0.025 B – H < 275’F Food types I, II, VI-A, VII-B, VIII
E – F – G All foods
PET 0.035 A – H All foods
Solvaperm Red G S.R.135 PET
Polysynthren Yellow NG P.Y.147 PET
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Food contact conditions :A – Container is sterilised over 212’FB – Container is sterilised with boiling waterC – Container is hot filled or pasteurised above 150’FD – Container is hot filled or pasteurised below 150’FE – Room temperature filled and stored. No thermal treatment in the containerF – Refrigerated storage. No thermal treatment in the containerG – Frozen storage. No thermal treatment in the containerH – Frozen or refrigerated storage. Ready prepared foods intended to be reheated
or microwaved in container at time of use
Food types :I – Non acid,aqueous: may contain salt/sugar (pH above 5.0)II – Acid, aqueuous; may contain salt/sugar and oil-in-water emulsions of low
or high fat contentIV-B – Oil-in-water emulsions, high or low fatVI-A – Beverages containing up to 8 percent alcoholVI-B – Beverages, non alcoholicVII-B – Moist bakery products with surface containing no free fat or oilVIII – Dry solids with the surface containing no free fat or oil (no end test required)
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Principles Behind REACH
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