Organic Pigment

78-1
7S
ÒrganIc ¡Igmenfs
78.1
78.2 The Coloui Index System.................................................78-1
78.3 Pigment Selection..............................................................78-2
Oiganic Yellows
78.1 Intruductiun
A defnition of a pigment, as distinct fiom a dyestuff, has been piepaied by the Diy Coloi Manufac-
tuieis` Association (DCMA) in iesponse to a iequest fiom the Toxic Substances Inteiagency Testing
Committee. This defnition should claiify the teim °pigment" and °dyestuff," which aie often eiione-
ously used inteichangeably:
Pigments aie coloied, black, white, oi ßuoiescent paiticulate oiganic and inoiganic solids which usually
aie insoluble in, and essentially physically and chemically unaffected by, the vehicle oi substiate
in which they aie incoipoiated. They altei appeaiance by selective absoiption and/oi by scatteiing
of light.
Pigments aie usually dispeised in vehicles oi substiates foi application, as foi instance in inks, paints,
plastics, oi othei polymeiic mateiials. Pigments ietain a ciystal oi paiticulate stiuctuie thioughout
the coloiation piocess.
As a iesult of the physical and chemical chaiacteiistics of pigments, pigments and dyes diffei in theii
application; when a dye is applied, it penetiates the substiate in a soluble foim aftei which it may oi
may not become insoluble. When a pigment is used to coloi oi opacify a substiate, the fnely divided,
insoluble solid iemains thioughout the coloiation piocess.
78.2 The Cu!uur Index System
The Coloui Index System is a coding system as developed undei the joint sponsoiship of the Society of
Dyeis and Colouiists (SDC) in the United Kingdom and the Association of Textile Chemists and Coloiists
(AATCC) in the United States. The system is iefeiied to as the °Coloui Index." (This system is iegisteied
as a tiade name and the use of the °u" in °Coloui" must be ietained.) By giving a compound a °Coloui
Index Name" and a °Coloui Index Numbei," a coloied compound can be ieadily placed into a classif-
cation accoiding to its chemical constitution and coloi. This desciiption is iecognized by many govein-
ment bodies as adequate infoimation foi inclusion in hazaid data sheets oi mateiial safety data sheets
to fully identify the pigment in question and to piovide accuiate iefeience when including a pigment in
any inventoiy listing. Thus, foi example, phthalocyanine blue has a Coloui Index name Pigment Blue
15 and the Coloui Index numbei 74160.
¡efer A. LevIs
Sun C|emíco| Cor¡ororíon
© 2006 by Taylor & Erancis Group, LLC
Intioduction ......................................................................78-1
Oiganic Blues · Oiganic Gieens · Oiganic Oianges · Reds ·
78-2 Cooríng· Tec|no|ogy Hondboo|, T|írd ídíríon
The Coloui Index names foi pigments aie abbieviated as follows:
PB · Pigment Blue
PBi · Pigment Biown
PM · Pigment Metal
PV · Pigment Violet
PW · Pigment White
PBk · Pigment Black
PG · Pigment Gieen
PO · Pigment Oiange
PR · Pigment Red
PY · Pigment Yellow
Additionally, the Coloui Index constitution numbei conveys infoimation iegaiding the stiuctuie of
the compound as shown in Table 78.1.
78.3 Pigment Se!ectiun
Once a foimulatoi has decided upon the hue that is iequiied foi a paiticulai coating, the next most
impoitant ciiteiia of any pigment aie its fastness piopeities. It is useless to foimulate any coating with
a pigment that will not withstand the exposuie specifcations of the coating`s end use. Such specifcations
can extend to iequiiing as much as 5 yeais` outdooi exposuie in states such as Floiida and Aiizona.
Due attention must be paid to the iespective manufactuieis` liteiatuie to ensuie that a pigment has
been chosen that will satisfy the end-use ciiteiia foi stability to ßocculation and ciystallization, as well
as fastness to light, solvents, heat, and chemicals. Once a pigment class has been selected that will
peifoim adequately in the end-use application, the foimulatoi can considei such othei factois as
economy. The foimulatoi should be awaie, howevei, that the fastness piopeities of a pigment will be
affected by the medium into which it is incoipoiated. Thus, even though intiinsically the pigment may
featuie the iequiied piopeities, it is still necessaiy foi the fnal pigmented coating to be tested in the
end-use application.
TABLE 78.1 Range of Coloui Index Constitution Numbeis
Chemical Class Coloui Index Constitution Numbei
Insoluble Azo
1. Acetoacetyl 11640-11790
2. Heteiocyclic hydioxy 12600-12825
3. Disazo 11640-11790
4. 2-Naphthol 20000-29999
5. 3-Hydioxy-2-naphthanilide 12300-12520
Piecipitated Azo
1. 2-Naphthol (sulfonic) acid 15500-16815
Piecipitated Nonazo
1. Xanthene 45000-45999
2. Tiiphenylmethane 42000-44999
Insoluble Nonazo
1. Phthalocyanine 74000-74999
2. Anthiaquinine 58000-72999
3. Quinaciidone 73900-73999
Orgoníc Pígmenr· 78-3
78.3.1 Organic B!ues
78.3.1.1 Cupper Phtha!ucyanine B!ue
The majoi blue used within the coatings industiy is coppei phthalocyanine blue (PB 15), with its usage
fai outweighing othei blues such as Indathione blue (PB 60).
Phthalocyanines aie planai molecules with a tetiabenzotetiaazopoiphin stiuctuie as shown in Figuie
78.1. Manufactuie is compaiatively easy despite the supeifcial complexity of the phthalocyanine mole-
cule. Reaction of a phthalic acid deiivative at tempeiatuies appioximating 190C with a souice of nitiogen
such as uiea and a metal oi metal salt is usually all that is iequiied to pioduce the appiopiiate metal
phthalocyanine. Molybdate, vanadates, and ceitain compounds of titanium have been found to be useful
catalysts foi this condensation ieaction.
Figuie 78.2 illustiates the chemistiy behind the pioduction of coppei phthalocyanine blue. This
condensation ieaction iesults in the foimation of coppei phthalocyanine in a ciude, nonpigmentaiy
foim. The pioduct has thus to be fnished oi conditioned to give the pigment giade of choice. Typically
ciude phthalocyanine blue is chaiacteiized by a ciystal size of the oidei of 50 m, a puiity in excess of
92%, and a pooi pigmentaiy stiength.
Metal-fiee phthalocyanine blue (PB 16) is noimally manufactuied via the sodium salt of phthalonitiile.
Acid pasting is used to condition the ciude and give the pigment.
Coppei phthalocyanine is commeicially available in two ciystal foims known as the and . The
foim is desciibed by the designations Pigment Blue 15, 15:1, and 15:2 and is a biight ied-shade blue
pigment. The foim is desciibed as Pigment Blue 15:3 and 15:4 and is a biight gieen oi peacock shade.
The foim is meta-stable and iequiies special tieatment to stabilize the ciystal against its tendency to
FIGURE 78.1 Stiuctuie of coppei phthalocyanine blue (pigment blue 15).
FIGURE 78.2 Chemistiy of coppei phthalocyanine.
a
Molybdate oi vanadate.
N
N N
N
N
N
N N
C
C C
C C
C
C C
Cu
O O
O
O
NH
NH
NH
O
4
NH
NH
O
NH
NH
NH
NH
Urea
Heat
Copper Salt
Catalyst
a
Heat
Copper
Complex N
N N
N
N
N
N N
C
C C
C C
C
C C
Cu
ieveit to the moie stable, gieen-shade ciystal. If eithei of the unstable ciystal foims (PB 15 oi 15:1)
is used with stiong solvents, conveision to the foim will occui upon stoiage of the system. Conveision
fiom the to the foim is usually accompanied by an inciease in ciystal size with subsequent loss of
stiength and shift to a gieenei hue.
As stated eailiei, coppei phthalocyanine gives excellent seivice in most coatings applications, but theie
is consideiable vaiiation between both the chemical and ciystal types available.
Pigment Blue 15 is an ciystal with the ieddest shade of the types commonly available. It is the least
stable of the family and as such is often iefeiied to as ciystallizing ied-shade (CRS) blue. This ciystal
foim cannot be used in any solvent containing systems.
Pigment Blue 15:1 is also an ciystal, but chemical modifcations have been made to stabilize the
stiuctuie against ciystallization. Most commonly the molecule is chloiinated to the extent of intioducing
one chloiine molecule to give °monochloi" blue. Anothei technique involves the use of a substituted
phthalocyanine, added to the pigment at levels appioaching 10 to 15%, that confeis ciystal stability to
the system. The monochloiinated giade is, as a consequence of the intioduced chloiine atom, gieenei
than the additive-stabilized ciystal.
Pigment Blue 15:2, desciibed as °nonciystallizing nonßocculating" ied-shade blue, is widely used
within the coatings industiy. The pioduct is an ciystal that is stabilized against both ciystallization
and ßocculation using additive technology.
Pigment Blue 15:3 iepiesents the gieen-shade, ciystal phthalocyanine blue and, as it exists in the
stable ciystal foim, it is less susceptible to ciystallization. Most commeicial giades of Pigment Blue 15:3,
howevei, contain fiom 4 to 8% of the ciystal, which will be adveisely affected by stiong solvent systems.
A 100% blue is too dull, opaque, and weak to be commeicially attiactive; hence, a piopoition of the
ciystal is left in the system, contiibuting consideiably to the attiactiveness of the system.
Pigment Blue 15:4 iepiesents a blue that has been modifed with phthalocyanine-based additives to
give a gieen-shade blue that is iesistant to ßocculation and can be used in stiong solvent systems.
Coppei phthalocyanine appioximates the ideal pigment. It offeis stiength, biightness, economy, and
all-aiound excellent fastness piopeities. Peihaps the pigment`s only disadvantages aie its tendencies to
change to a coaise, ciystalline, nonpigmentaiy foim in stiong solvents and to ßocculate oi sepaiate fiom
white pigments when used in paints and lacqueis.
78.3.1.2 Misce!!aneuus B!ues
Although the oiganic blues used in the coatings industiy aie piimaiily coppei phthalocyanines, biief
mention must be made of othei blue pigments that fnd use in the coatings maiketplace.
Indanthione blue, Pigment Blue 60, belongs to the class of pigments desciibed as °vat pigments." This
pigment is expensive ielative to coppei phthalocyanine, and thus economic consideiations aie a limitation
to its widespiead use. Idanthione blue is a veiy ied-shade pigment with outstanding fastness piopeities.
Caiabazole violet, Pigment Violet 23, is a complex polynucleai pigment that is a veiy valuable ied-
shade blue of high tinctoiial stiength. The pigment possesses excellent fastness piopeities, and only its
ielatively high cost and its haid natuie limit its moie widespiead use. Fiom an economic standpoint it
costs appioximately thiee times as much as phthalocyanine blue.
The pigment is used as a shading component in high peifoimance coatings that call foi paiticulaily
ied-shade blue.
78.3.2 Organic Greens
78.3.2.1 Cupper Phtha!ucyanine Green
The majoi gieen pigment used as a self shade in the coatings industiy is based on halogenated coppei
phthalocyanine and, as such, is teimed phthalocyanine gieen. The Coloui Index names aie Pigment
Gieen 7 and Pigment Gieen 36.
Pigment Gieen 7, the blue-shade gieen, is based on chloiinated coppei phthalocyanine with a chloiine
content that vaiies fiom between 13 to 15 atoms pei molecule.
Pigment Gieen 36, the yellowei shade, is based on a stiuctuie that involves the piogiessive ieplacement
of chloiine on the phthalocyanine stiuctuie with biomine. The composition of Pigment Gieen 36 vaiies
with iespect to the total halogen content, chloiine plus biomine, and in the iatio of biomine to chloiine.
Figuie 78.3 illustiates the pioposed stiuctuies of the phthalocyanine gieens. In piactice, no single pigment
consists of a specifc-moleculai species; iathei, each pigment is a complex mixtuie of closely ielated
isomeiic compounds.
These pigments aie ideal, since theii tinctoiial and fastness piopeities allow theii use in the most
seveie application situations. They possess outstanding fastness to solvents, heat, light, and outdooi
exposuie. They can be used in masstone shades and tints down to the veiy palest of depths.
Phthalocyanine gieens aie manufactuied by a thiee-step piocess: ciude phthalocyanine blue is fist
manufactuied, then halogenated to give a ciude coppei phthalocyanine gieen, and fnally conditioned
to give the pigmentaiy pioduct.
78.3.2.2 Misce!!aneuus Greens
may fnd some minoi application in the coatings industiy.
FIGURE 78.3 Stiuctuie of coppei phthalocyanine gieens.
C
C C
C
C C
Cu
Br
Br Br
Br Br
Br Cl
Cl
Cl
Cl
Cl
Cl
N N
C C N N
N N
N
N
C
C C
C
C C
Cu
Br
Br Br
Br Br
Br
Br
Cl
Cl Cl
Br
Br
N N
C C N N
N N
N
N
Pigment
Green 36
(Bluest shade
also known
as 3y)
C
C C
C
C C
Cu
Cl
Cl Cl
Cl
Cl
Cl
Cl
Cl
Cl Cl
Cl
Cl Cl
Cl
Cl
N N
C C N N
N N
N
N
Pigment Green 7
Pigment
Green 36
(yellowest
shade also
known as 6y)
Table 78.2 gives a summaiy of the piopeities of some othei commeicially available oiganic gieens that
78.3.3 Organic Oranges
Table 78.3 lists the oiange pigments that aie available in today`s maiketplace. A bioad subdivision can
be made based on such chemical featuies of the molecule as azo based, benzimidazolone based, and
miscellaneous oianges.
78.3.3.1 Azu-Based Oranges
Pigment Crange 2, Oithonitioaniline Oiange, is piepaied by the classical diazotization and coupling
technique in which diazotized oithonitioaniline is coupled to -napthol. The pigment`s majoi
maiket is in the feld of piinting inks. Its use in coatings is not iecommended because the pigment`s
solvent fastness is pooi and its lightfastness inadequate.
Pigment Crange 5, Dinitioaniline Oiange, is manufactuied by a diazotization and coupling sequence
in which diazotized dinitioaniline is coupled onto -napthol. This pigment offeis good lightfast-
ness in full tone and modeiate solvent fastness. As such, the pigment fnds widespiead use in
TABLE 78.2 Summaiy of Miscellaneous Gieen Piopeities
Coloui Index Name Chemical Name Comments
PG 1 Biilliant Gieen
(Tiiphenylmethane PTMA)
Biilliant, blue shade; pooi alkali and soap iesistance, solvent bleed,
and lightfastness; may be used in inteiioi fnishes.
PG 2 Peimanent Gieen
Blend of Pigment Gieen 1 and Pigment Yellow 18; biight yellow
shade; pooi fastness oveiall
PG 4 Malachite Gieen
Biight, blue shade; pooi fastness piopeities oveiall
PG 8 Pigment Gieen B (Nitioso) Yellow shade; dull hue; pooi fastness piopeities; may be used in
inteiioi emulsions
PG 10 Gieen Gold Yellow shade; loses metal in stiong acid oi alkali; good lightfastness;
modeiate solvent fastness; used in automotive and exteiioi paints
TABLE 78.3 Oiganic Oiange Pigments
Coloui Index Name Coloui Index Numbei
a
Chemical Type
PO 2 12060 Azo
PO 5 12075 Azo
PO 13 21110 Bisazo
PO 16 21160 Bisazo
PO 31 n/a Bisazo condensation
PO 34 21115 Bisazo
PO 36 11780 Benzimidazalone (azo)
PO 38 12367 Azo
PO 43 71105 Peiinone
PO 46 15602 Azo
PO 48 n/a Quinaciidone
PO 49 n/a Quinaciidone
PO 51 n/a Pyianthione
PO 52 n/a Pyianthione
PO 60 n/a Benzimidazolone (azo)
PO 61 n/a Tetiachloioisoindolinone
PO 62 n/a Benzimidazolone (azo)
PO 64 n/a Heteiocyclic hydioxy
PO 67 n/a Pyiazoloquinazolone
a
n/a Not assigned.
The stiuctuie of the seven oiange pigments that can be placed into the °azo" categoiy aie shown in Figuie
78.4 and aie listed below:
FIGURE 78.4 Stiuctuie of azo-based oianges.
NO
2
N
N
N N N
C
C
CH
N
HO
NO
2
O
2
N N N
HO
Cl
SO
3
N N
HO
Orthonitroaniline Orange
PO 2
PO 5
PO 13
PO 16
PO 34
PO 38
PO 46
Dinitroaniline Orange
N
C
COCH
3
CH
3
O
Cl
CH
3
Pyrazolone Orange
2
N
N N
N N
C
CH
CH
3
H
3
C
H
2
N
O
Cl
2
2
NH C
O
C
O
C NH
O
N N CH
Dianisidine Orange
Tolyl Orange
Cl HO NHCOCH
3
Naphthol Orange
H
5
C
2
Clarion Red
Ba
2+
2
78-S Cooríng· Tec|no|ogy Hondboo|, T|írd ídíríon
latex-based paints and, with the exception of high bake enamels, in both aichitectuial and
industiial coatings.
Pigment Crange 13, Pyiazolone Oiange, is synthesized by coupling tetiazotized 3,3-dichloiobenzidine
onto 3-methyl-1-phenyl-pyiazol-5-one. The pigment is a biight, clean yellow-shade pioduct that
is tinctoiially stiongei than Pigment Oiange 5. It may be iecommended foi inteiioi coatings,
paiticulaily as a ieplacement foi lead-based oianges.
Pigment Crange 1õ, Dianisidine Oiange, is a diaiylide oiange that is piepaied by coupling tetiazotized
3,3-dimethoxybenzidine onto acetoacetanilide. The pigment fnds use in baking enamels, since its
heatfastness is supeiioi to that of othei oiange pigments with similai economics. Usage in inteiioi
coatings at full tone levels is also iecommended.
Pigment Crange 34, Tolyl Oiange, is pioduced by coupling tetiazotized 3,3-dichloiobenzidine onto 3-
methyl-1-(4-methyl-phenyl)-pyiazo-5-one. The pigment is a biight, ieddish oiange that offeis
modeiate lightfastness and good alkali iesistance, but pooi solvent fastness. As such, the mateiial
is used in inteiioi coatings applications, paiticulaily wheie a lead-fiee foimula is specifed.
Pigment Crange 38, Naphthol Oiange, is manufactuied by coupling diazotized 3-amino-4-chloioben-
zamide onto 4-acetamido-3-hydioxy-2-napthanilide. The pigment is a biight ieddish oiange
that exhibits excellent alkali and acid fastness, modeiate solvent fastness, and acceptable light-
fastness when used at full tint. As such, the pigment fnds use in baking enamels, latex, and
masoniy paints.
Pigment Crange 4õ, Claiion Red, is a metallized azo pigment manufactuied by coupling diazotized 2-
amino-5-chloio-4-ethylbenzene-sulfonic acid onto -napthol and metallizing the pioduct with
baiium to yield the pigment. The pigment has pooi lightfastness, infeiioi alkali iesistance, and
inadequate solvent fastness, hence is not iecommended foi use in coatings.
78.3.3.2 Benzamidazu!une-Derived Oranges
The thiee benzimidazolone-deiived oianges contain the azo chiomophoie and aie all based on the 5-
acetoacetylaminobenzimidazolone as the coupling component.
Pigment Oiange 36 is the pioduct of coupling diazotized 4-chloio-2-nitioaniline to the benzimida-
zolone. Pigment Oiange 60 is the pioduct of the coupling of 4-nitioaniline to the benzimidazolone.
Because of the piopiietaiy natuie of this pioduct, the stiuctuie of Pigment Oiange 62 has not been fully
declaied (Figuie 78.5 illustiates two typical stiuctuies):
Pigment Crange 3õ is a biight ied-shade oiange of veiy high tint stiength. The opacifed foim of this
pigment offeis excellent fastness piopeities to both heat and solvents and a hue similai to the lead
containing pigment, Molybdate Oiange (PO 104). As such, Pigment Oiange 36 fnds majoi use
in lead-fiee automotive and industiial high peifoimance coatings.
FIGURE 78.5 Stiuctuie of the benzimidazolone oianges.
C
C C
C
Cl
N N
H
N
H
H
N
N
NO
2
H
3
C
PO 36
PO 60
O
O
O
C
C C
C
NO
2
N N
H
N
H
H
N
N
H
3
C O
O
O
Benzimidazolone Orange
Pigment õ0 is a tianspaient, yellow-shade oiange that also exhibits excellent heat and solvent fastness
with an exteiioi duiability that allows the pigment to be used in high quality industiial and
automotive fnishes.
Pigment Crange õ2 is also a yellow-shade oiange that shaies the lightfastness piopeities of the othei
two oianges. Cuiiently it is used in oil-based inks and aitists` colois. Its use in the coatings industiy
has yet to be fully exploied.
78.3.3.3 Misce!!aneuus Oranges
The stiuctuies of Pigment Oiange 53, a pyianthione, Pigment Oiange 64, a heteiocyclic hydioxy, and
Pigment Oiange 67, a pyiazoloquinazolone, have not been fully declaied. Table 78.4 summaiizes the
piopeities of this class of pigments, which iepiesents a seiies of oianges that aie fnding incieased
application in the coating industiy.
78.3.4 Reds
78.3.4.1 Meta!!ized Azu Reds
Many of the ieds used in the coatings industiy fall into the chemical categoiy of azo pigments because
the azo chiomophoie -N·N- is a featuie of the molecule.
A fuithei subdivision may be made into acid, monazo metallized pigments such as Manganese Red 2B
(PR 48:4) and Calcium Lithol (PR 49:2) and nonmetallized azo ieds such as the Naphthols (e.g. PR 17
and PR 23) and Toluidine Red (PR 3). Typically, each of the acid, monoazometallized pigments contains
an anionic giouping such as a caiboxylic (-COOH) oi sulfonic acid (-SO
3
H) gioup, which will ionize
and ieact with a metal cation such as calcium oi manganese to foim an insoluble, metallized pigment.
Nonmetallized pigments do not contain an anionic gioup in theii stiuctuie and, as such, will not
complex with a metal cation.
All azo ieds contain one oi moie azo gioups and aie pioduced by similai ieaction sequences. The
initial ieaction sequence, desciibed as diazotization, involves ieacting an aiomatic piimaiy amine with
nitious acid, foimed in situ by ieacting sodium nitiite with hydiochloiic acid at low tempeiatuies to
yield a diazonium salt. Invaiiably the diazonium salt that is foimed by this piocess is unstable and should
be kept cold to avoid any decomposition.
The diazonium salt is ieacted quickly with the second half of the pigment, which is called the couplei.
The coupling ieaction takes place iapidly in the cold to yield the sodium salt of the pigment. This sodium
salt is all but useless as a pigment foi the coatings industiy because of its maiked tendency to bleed even
TABLE 78.4 Summaiy of the Piopeities of the Miscellaneous Oianges
Coloui Index Name Common Name/Desciiption Piopeities
PO 43 Peiinone Red shade, stiong, clean, vat pigment with excellent fastness
piopeities; used in metallized fnishes and high giade paints;
shows slight solvent bleed
PO 48 Quinaciidone Gold Yellow shade; excellent lightfastness; lacks biightness in masstone;
used in metallic fnishes
PO 49 Quinaciidone Deep Gold Red shade; dull masstone; excellent duiability; used in metallics
PO 51 Pyianthione Oiange Medium shade; excellent fastness to solvent, light, and heat; dull in
tin; exhibits slight solvent bleed; used in aii diy and bake enamels
PO 52 Pyianthione Oiange, ied
shade
Vat pigment with excellent fastness to solvent, light, and heat; dull
in tints; slight solvent bleed; used in aii diy and bake enamels
PO 61 Tetiachloioisoindolinone
oiange
Medium shade; exhibits some solvent bleed; used in metallic
automotive fnishes
PO 64 Biight shade ied Excellent solvent and lightfastness; used in industiial coatings
PO 67 Yellow shade Excellent biilliance in full shade; good gloss ietention; veiy good
weathei- and lightfastness in full shade; used in industiial and
automotive coatings
in the weakest of solvent systems. The pigment is, theiefoie, metallized to confei impioved piopeities
on the pioduct. The pigment suspension is then flteied and washed to iemove any iesidual inoiganics
deiived fiom the ieaction.
Figuie 78.6 illustiates the stiuctuies of the diffeient metallized azo ieds that aie ieadily available.
The Iithcl Reds aie piimaiily Baiium Lithol (PR 49:1) and Calcium Lithol (PR 49:2). Although limited
in theii application in the coating industiy, these pigments do fnd some use at masstone levels - that
is, the pigment is not tinted with a white tint base - wheie theii fastness piopeities aie acceptable.
The pigments aie biight ieds with high tint stiength and good dispeision chaiacteiistics. The baiium
salt is lightei and yellowei in hue compaied to the calcium salt.
Permanent Red 2B is the geneiic name that encompasses Baiium Red 2B (PR 48:1), Calcium Red 2B
(PR 48:2), and Manganese Red 2B (PR 48:4). The majoi use of the calcium and baiium salts is in baked
industiial enamels, which aie not iequiied to be fast to outdooi exposuie. Use in alkaline systems is
seveiely iestiicted because of the pooi alkaline fastness of these salts.
FIGURE 78.6 Metallized azo ieds.
Lithol Rubine
Add Cl
CH
3
N
HO COO
N
SO
3
CH
3
CH
3
N
HO COO
N
SO
3
PR 57
PR 48
PR 52
Cl
CH
3
N
HO COO
N
SO
3
Cl
PR 200
PR 53
PO 46
C
2
H
5
N
HO COO
-COO Subtract-COOH
N
SO
3
Cl
C
2
H
5
C
2
H
5
N
HO
N
SO
3
Cl
CH
3
N
HO
N
SO
3
Cl
C
2
H
5
Bon Red
Exchange
Positions
CH
3
CH
3
Methylene (-CH
2
-) Addition
Clarion Red
Subtrat CH
2
Red Lake C
Cl
Red 2B
The baiium salt is chaiacteiized by a clean, yellow hue and, although slightly pooiei than the bluei
calcium salt in lightfastness and tinting stiength, it does possess a slight advantage in bake stability.
Manganese Red 2B has a suffciently impioved lightfastness to be used in implement fnishes. The
manganese salt is slightly bluei, diitiei, and less intense when compaied to the calcium salt.
Rubine Red also known as Calcium Lithol Rubine (PR 57:1) is a clean, blue-shade ied pigment
exhibiting the high tinting ability typical of the azo ieds of this class. Its majoi use in coatings is in
inteiioi systems that call foi an inexpensive ied with good solvent and heat iesistance. Again, to maintain
maximum fastness piopeities, use of the pigment at neai to masstone levels is iecommended.
BCN red, used as calcium BON Red (PR 52:1) oi Manganese BON Red (PR 52:2), is chaiacteiized
by outstanding cleanliness, biightness, and puiity of coloi. The manganese salt offeis a veiy blue-shade
ied with impioved lightfastness compaied to the calcium salt. As such, this salt is suitable foi exteiioi
coatings applications.
BCN Marccn, (PR 63:1) is illustiated in Figuie 78.7; the manganese salt of BON Maioon is of
consideiably moie impoitance than eithei the calcium oi baiium salts. Its lightfastness is such that the
pigment can be used at masstone levels foi implement fnishes.
78.3.4.2 Nunmeta!!ized Azu Reds
As implied by theii classifcation, the nonmetallized azo ieds do not contain a piecipitating metal cation
and, as such, offei incieased stability against hydiolysis in stiongly acidic oi alkaline enviionments.
Synthesis of this class of pigment follows the pieviously desciibed classical method of diazotization of
a piimaiy aiomatic amine followed by coupling of the iesultant diazonium salt. No anionic gioups
capable of accepting a metal cation aie piesent in the molecule; thus metallization is not a factoi in theii
synthesis. Typical nonmetallized ieds aie Toluidine Red (PR 3) and the wide iange of Napthol Reds as
iepiesented by Pigment Reds 17, 22, and 23.
Toluidine Red is used in full shade in such coatings applications as faim implements, lawn and gaiden
equipment, and bulletin paints, wheie a biight, economical ied of adequate lightfastness is iequiied.
Because of the pigment`s pooi duiability in tint shades, it is iaiely used at any level othei than a full shade.
The individual piopeities of the Napthol Reds depend on the specifc composition of the pioduct as
well as the conditioning steps used duiing pigment manufactuie. As a class, they aie a gioup of pigments
that exhibit good tinctoiial piopeities combined with modeiate fastness to heat, light, and solvents.
Unlike the metallized azo ieds, the Napthol Reds aie extiemely iesistant to acid, alkali, and soap. These
piopeities lead to theii use in latex emulsion systems and masoniy paint.
In teims of peifoimance and economic chaiacteiistics, the Napthols foim a link between the toluidine
ieds at the lowei end of the scale and the peiylene and quinaciidone ieds at the highei end.
78.3.4.3 High Perlurmance Reds
Pigments foi the exacting standaids of today`s automotive coatings aie iequiied to show satisfactoiy
duiability to outdooi exposuie in such states as Aiizona and Floiida foi 2 and possibly 5 yeais befoie
being appioved foi use in automotive fnishes. Similai iequiiements aie placed on pigments chosen foi
use in automotive iepaii systems and maiine coatings.
FIGURE 78.7 BON maioon.
N
HO COO
Ca
2+
N
SO
3
High peifoimance ieds fall into foui basic classes: quinaciidone ieds and violets, ieds based on vat
dyestuffs known to include the peiylene ieds, ieds deiived fiom the benzimidazolone diazonium salts,
and the disazo condensation ieds.
78.3.4.3.1 Quínacrídone Reds
Quinaciidones may be desciibed as heteiocyclic pigments in that theii stiuctuie compiises a fused iing
stiuctuie in which the iing atoms aie dissimilai. In the case of quinaciidones, the iing atoms aie caibon
and nitiogen (Figuie 78.8). Addition of diffeiing auxochiomic gioups such as methyl (-CH
3
) and
chloiine (-Cl) gives Pigment Red 122 and Pigment Red 202, iespectively.
The two most commeicialized ioutes in the synthesis of quinaciidone (PV 19) involve eithei the
oxidation of dihydioquinaciidone oi the cyclization of 2,5-diaiylaminotei-ephthalic acid as outlined in
Figuie 78.9. Subsequent conditioning leads to the desiied ciystal modifcation. Use of 2,5-diaiylamino-
FIGURE 78.8 Stiuctuie of tianslineai quinaciidone.
FIGURE 78.9 Routes to quinaciidone.
C
N
H
N
H
O
C
O
A. CycIization of 2, 5-diaryIaminoterephthaIic Acid
CH
2
COOC
2
H
5
CH
2
COOC
2
H
5
CH
2
COOC
2
H
5
CH
2
COOC
2
H
5
(i) cyclization
(ii) + aniline
(iii) oxidation
NH
NH
COOC
2
H
5
COOC
2
H
5
C
2
H
5
OOC
C
2
H
5
OOC
Ring Closure
in Polyphosporic Acid
C
N
H
N
H
O
C
C
N
H
N
H
H H
H H
O
C
O
O
O
O
COOH
HOOC
N
N
oxidation
trans
linear
quinacridone
B. Oxidation of dihydroquinacridone
teiephthalic acid at the cyclization stage yields the unsubstituted tians lineai quinaciidone. Use of 2,5-
ditoluidinoteiephthalic acid yields the 2,9-dimethyl quinaciidone, Pigment Red 122.
As a gioup of high peifoimance pigments, quinaciidones fnd theii piimaiy uses in automotive
fnishes, both metallic and solid shades, industiial fnishes, and exteiioi fnishes.
The pigments combine excellent tinctoiial piopeities with outstanding duiability, solvent fastness,
lightfastness, heatfastness, and chemical iesistance. Table 78.5 lists the shades cuiiently available.
78.3.4.3.2 Vat Reds
The ied pigments, based on anthiaquinine, include such stiuctuies as Anthiaquinone Red (PR 177),
Peiinone Red (PR 194), Biominated Pyianthone Red (PR 216), and Pyianthone Red (PR 226), as
These anthiaquinone-deiived pigments aie manufactuied via a seiies of complex ieactions to include
such piocessing as sulfonation, nitiation, halogenation, condensation, and substitution.
78.3.4.3.3 Perylene Reds
Peiylene ieds piovide puie, tianspaient shades and novel styling effects when used in metallic fnishes.
These pigments offei impioved ßow chaiacteiistics when used in highly pigmented coatings foimulations
such as those iequiied foi high solids base coat/cleai cost systems, as well as high tianspaiency and good
bleed iesistance.
The peiylenes possess high coloi stiength, good theimal stability, excellent light- and weatheifastness
and, with the exception of Pigment Red 224, excellent chemical iesistance.
Peiylenes may also be desciibed as vat pigments and in fact aie the only class of vat pigments to be
specifcally developed as pigments iathei than as dyestuffs. Almost all the peiylene pigments have a
Acenaphthene is oxidized to 1,8-naphthalic anhydiide followed by ammonation to yield the naphthal-
imide. The napthalimide is condensed in a fused caustic medium to yield the peiylene-3,4,9,10-tetiacai-
Pigment Violet 26, oi methylated to give Pigment Red 179.
The diimide may be hydiolyzed to pioduce the dianhydiide, Pigment Red 224, oi condensed with
many of the pigments alieady desciibed, the peiylenes have to be conditioned to obtain the compounds
in a pigmentaiy foim.
78.3.4.3.4 Thíoíndígo Reds
The thioindiogoid chiomophoie seives as a nucleus foi a wide iange of ied to violet pigments. The
thioindigo ieds include Pigment Reds 36, 87, 88, 181, and 198. These pigments aie noted foi theii
TABLE 78.5 Types of Quinaciidone
Coloui Index Name Hue Comments
PO 48 Gold Quinaciidone quinone
PO 49 Deep Gold Quinaciidone quinone
PR 122 Magenta-yellow 2,9-Dimethyl quinaciidone
PR 192 Red-yellow Unsymmetiical monomethyl quinaciidone
PR 202 Magenta-blue 2,9-Dichloioquinaciidone
PR 206 Maioon Mixed solid solution
PR 207 Scailet 4,11-Dichloioquinaciidone
PR 209 Yellow-shade ied 3,10-Dichloioquinaciidone
PV 19 Violet-blue -Quinaciidone
Red-yellow -Quinaciidone
PV 42 Maioon Mixed solid solution
illustiated in Figuie 78.10.
stiuctuie as shown by the geneiic foimula illustiated in Figuie 78.11; that is; they aie based on N,N-
substituted peiylene-3,4,9,10-tetiacaiboxylic diimide. A notable exception is Pigment Red 224 (Figuie
boxylic acid diimide. The diimide can then be conditioned to conveit the ciude into pigment and achieve
78.12), which is actually deiived fiom the peiylene tetiacaiboxylic dianhydiide.
vaiious aiomatic oi aliphatic amines to give such pigments as those featuied in Figuie 78.13. As with
biightness of shade and all-aiound good fastness piopeities. These piopeities have iesulted in the use of
the thioindigoes in quality coatings; Pigment Red 88 is the piime pigment, followed by Pigment Red 198.
78.3.4.3.5 Benzímídazolone-Based
The benzimidazolone pigments featuie Pigment Reds 171, 175, 176, 185, and 208. These pigments aie
azo-based compounds that contain the benzimidazolone stiuctuie as pait of theii coupling component.
Although used piimaiily foi the coloiing of plastics because of theii outstanding theimal stability, this
class of pigments does fnd application in the coatings industiy. Benzimidazolones show excellent fastness
to light, good weatheiability, and excellent fastness to oveispiaying at elevated tempeiatuies. The benz-
imidazolone pigments aie piepaied using the diazotization and coupling techniques desciibed eailiei.
Geneially, aftei the coupling piocess, the pigment is tieated to obtain a unifoim, contiolled ciystal
giowth and paiticle size distiibution.
FIGURE 78.10 Stiuctuie of tianslineai quinaciidone.
O
O
O
O
O
O
Anthraquinone Red (PR 177)
N
N
C
C
O
N
N
C
C
O
Perinone Red (PR 194)
Br
3
O
O
Br
2
Brominated Pyranthrone Red (PR 216)
Pyranthrone Red (PR 226)
FIGURE 78.11 Peiylene stiuctuies.
FIGURE 78.12 Pigment Red 224.
FIGURE 78.13 Peiylene synthesis.
O
O
C
C
R N
O
O
C
C
R N
R = -C
6
H
3
OC
2
H
5
PR 123 Vermillion
R = -C
6
H
3
(CH
3
)
2
PR 149 Scarlet
R = -CH
3
PR 179 Maroon
R = -C
6
H
5
OCH
3
PR 190 Red
R = -H PBr 26 Bordeaux
R = -C
6
H
5
Cl PR 189 Yellow Shade Red
R = N = N PR 178 Red
O
O
O
O
O
O
R-N
R-Cl
R-NH
2
H
2
SO
4
O
O
H
N O O
N-R
O
O
H-N
O
O
N-H
O
O
O
O
O
O
O
O
Typical Perylene Structure
2
Naphthalimide
NaOH fusion
Pigment Red 224
Perylene -3, 4, 9, 10-Tetracarboxylic
Acid di-lmide
78.3.4.3.o Dísazo Condensatíon Reds
These pigments featuie such piopeities as high tinctoiial stiength and fastness to solvents and heat. Disazo
condensation ieds have found consideiable use as ieplacement pigments foi lead containing pigments.
Theii outstanding fastness piopeities have iesulted in theii use in high quality industiial fnishes.
Figuie 78.14 illustiates thiee typical stiuctuies of the disazo condensation ieds. Coloui Index names
foi these thiee pigments have not been assigned. The synthesis sequence geneially is similai foi each of
the disazo condensation pigments. The azo components aie initially coupled to yield monoazo dyestuff
caiboxylic acids, which aie conveited to acid chloiides befoie fnal conveision to the disazo by conden-
sation with the aiylide component to yield the pigment in question.
78.3.4.3.7 Míscellaneous Hígh Performance Reds
In iecent yeais a numbei of novel high peifoimance ieds have been commeicialized by such companies
as Sandoz and BASF. New fiom Sandoz aie Pigment Reds 242, 214, and 257.
Pigment Red 242 is shown in Figuie 78.15. The pioduct is a yellow-shade ied with a clean biight shade
and veiy good all-aiound fastness piopeities. It is iecommended foi lead-fiee coatings foimulations foi
the pioduction of high quality fnishes and biight ied shades.
FIGURE 78.14 Stiuctuies of the disazo condensation ieds.
FIGURE 78.15 Stiuctuie of Pigment Red 242.
A N N
HO OH CO CO NH R NH
N N A
A
R
Cl
Cl
Cl
Red
M.Wt. 828.5
Cl
Cl
Cl
Cl
Cl
CH
3
Red
M.Wt. 863
Red
M.Wt. 803
CF
3
Cl Cl
Cl
N
N
OH
O
NH
CF
3
Cl
N
N
HO
O
NH
Pigment Red 214 (Figuie 78.16) is a bluish ied with piopeities similai to those of Pigment Red 242.
Pigment Red 257 (Figuie 78.17) is a nickel complex pigment with a ied violet masstone and a magenta
undeitone; its fastness piopeities aie similai to those of the quinaciidone pigments.
78.3.5 Organic Ye!!uvs
Yellow pigments can be subdivided into foui bioad classifcations based on theii chemical constitution.
These classifcations aie compiised of monoaiylide yellows, diaiylide yellows, benzimidazolone yellows,
and heteiocyclic yellows.
78.3.5.1 Munuary!ide Ye!!uvs
Monoaiylide yellows aie all azo pigments; theii manufactuie is based on the diazotization pioceduie,
Pigment Yellcw 1 is often iefeiied to as Hansa Yellow G foi histoiical ieasons. This pigment is a biight
yellow that fnds outlets in tiade sales, emulsion, and masoniy paints. The pigment`s majoi diawbacks
aie its pooi bleed iesistance, pooi lightfastness in tint shades, and maikedly infeiioi bake.
Pigment Yellcw 3, iefeiied to as Hansa Yellow 10G, is a pigment that is consideiably gieenei and cleanei
than Pigment Yellow 1. The pigment fnds a maiket in tiade sales, watei-based emulsions, and masoniy
paints. The pigment suffeis fiom the same defciencies of pooi bleed iesistance and pooi tint lightfastness
exhibited by Pigment Yellow 1. Pigment Yellow 3 is, howevei, suitable foi exteiioi use at high tint stiength.
Pigment Yellcw õ5 is a monaiylide yellow that fnds use in tiade sales, latex, and masoniy paints. The
pigment offeis a lightfastness in full shade of 7 and 67 in tint, a consideiable impiovement ovei Pigment
Yellow 1.
Pigment Yellcw 73 is a pigment close in shade to Pigment Yellow 1 which again fnds use in tiade sales,
latex, and masoniy paints. It is not, howevei, consideied to be duiable enough foi exteiioi applications.
Cl
Cl Cl
N
N
OH
O
NH
Cl
Cl
Cl
N
N
HO
O
NH
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
N
N
N H
H
H
H
N
N
N
O
O
Ni
followed by coupling. The stiuctuies of the majoi monoaiylide yellows aie iepiesented in Figuie 78.18.
78-1S Cooríng· Tec|no|ogy Hondboo|, T|írd ídíríon
Pigment Yellow 73 plays an impoitant iole in inteiioi, inteimix systems because of its stability against
ieciystallization in the piesence of glycols and wetting agents as used in aqueous systems.
Pigment Yellcw 74 offeis the usei a pigment that is suitable foi outdooi applications and consideiably
stiongei and somewhat gieenei than Pigment Yellow 1. Again usage in tiade sales, latex, and masoniy
paints is widespiead.
Pigment Yellcw 97 is a newei pigment that shows the advantages associated with a smallei paiticle size,
less agglomeiation, and an impioved paiticle size distiibution when compaied to the othei monoaiylide
yellows. Pigment Yellow 97 gained signifcant use in tiade sales applications piimaiily because it was
available when demands foi lead-fiee foimulations weie incieasing. Additionally, the pigment fnds use
in high quality decoiative paint.
Pigment Yellcw 98 is a pigment that has met with only limited commeicial success to date. The pigment
is similai in shade to Pigment Yellow 3 but is consideiably stiongei and moie heat stable; it fnds use in
tiade sales, masoniy, and latex-based paints.
Pigment Yellcw 11õ is a pigment similai in shade to light chiome yellow (PY34). Pigment Yellow 116
exhibits impioved chemical iesistance compaied to the othei monoaiylide yellows, showing impioved
fastness to solvent, heat, and light. Its majoi aiea of use is cuiiently in the foimulation of lead-fiee
coatings.
In summaiy, the monoaiylide yellows constitute the most impoitant class of oiganic yellows as
consumed by the coatings industiy. Because of the absence of any lake foiming gioups (e.g., -COOH
oi -SO
3
H) in theii stiuctuie, they possess excellent alkali fastness, which enables them to be used in all
majoi aqueous paint foimulations. Additionally, when compaied to theii inoiganic lead containing
counteipaits, the chiome yellows, the monoaiylides offei consideiably highei tinting stiength, biight
yellow hue of high chiome, and less tendency to daiken on exposuie to atmospheiic pollutants.
78.3.5.2 Diary!ide Ye!!uvs
piopeities of this class of yellows.
Basically, an inspection of the stiuctuies indicates that this class of yellows has a backbone stiuctuie
that hinges on 3,3-dichloiobenzidine with piopeities that diffei depending on the natuie of the coupling
component. Piopeities that aie common featuies of this gioup of yellows aie low cost, ieasonable heat
stability, and modeiate chemical iesistance.
FIGURE 78.18 Monoaiylide yellow stiuctuies.
H
3
C
NO
2
N N CH NH C
O
COCH
3
Cl
NO
2
N N CH NH C
O
COCH
3
PY 1
Hansa G
PY 3
Hansa 10G
Cl
O
2
N
OCH
2
OCH
3
N
NH S
N CH NH C
O
O
O
COCH
3
H
3
CO
N N CH NH C Cl
O
COCH
3
H
3
CO
OCH
3
H
3
CO
NO
2
N N CH NH C
O
COCH
3
H
3
CO
Cl
NO
2
N N CH NH C
O
COCH
3
H
3
CO
Cl Cl
NO
2
N N CH NH C
O
COCH
3
CH
3
NHCOCH
3
Cl
N N CH NH C
O
COCH
3
PY 65
PY 73
OCH
CONH
2
PY 74
PY 97
PY 98
PY 116
Figuie 78.19 illustiates the stiuctuie of the diaiylide yellows, and Table 78.6 piesents a summaiy of the
The majoi maiket foi the diaiylide yellows is the piinting ink industiy. The diaiylide yellows aie
appioximately twice as stiong as the monoaiylide yellows; additionally they offei impioved bleed iesis-
tance and fastness to heat. Howevei, none of the diaiylide yellows has duiability adequate foi the pigment
to be consideied in exteiioi coatings applications; thus the diaiylide yellows should not be used in any
outdooi situations.
78.3.5.3 Benzimidazu!une Ye!!uvs
zolone yellows because each is an azo pigment deiived fiom 5-acetoacetyl-aminobenzimidazolone.
The exceptional fastness to heat and the excellent weatheifastness of this class of pigments aie attiibuted
to the stiuctuial piesence of the benzimidazolone gioup.
Used initially foi coloiing plastics, these pigments aie fnding incieased use in coatings systems, wheie
theii excellent weatheifastness, heat stability, and fastness to oveistiipping aie iequiied (e.g., when
imidazolone yellows.
78.3.5.4 Heterucyc!ic Ye!!uvs
This class of pigments contains an assoitment of yellows that all contain a heteiocyclic molecule in theii
such stiuctuies, these new high peifoimance pigments continue to be intioduced into the maiketplace
FIGURE 78.19 Diaiylide yellow stiuctuies.
NH N CH N C
O
COCH
3
PY 12
Cl
2
H
3
C NH N CH N C
O
COCH
3
PY 13
Cl
2
CH
NH N CH N C
O
COCH
3
PY 14
Cl
2
CH
3
NH N CH N C
O
COCH
3
PY 16
CH
3
2
Cl
Cl
NH N CH N C
O
COCH
3
PY 17
Cl
2
OCH
3
NH N CH N C
O
COCH
3
PY 55
Cl
2
H
3
C
NH N CH N C
O
COCH
3
PY 81
2
CH
3
H
3
C
Cl
Cl
NH N CH N C
O
COCH
3
PY 113
2
CH
3
Cl
Cl
Cl
NH N CH N C
O
COCH
3
PY 83
2
OCH
3
OCH
3
CÌ
Cl
NH N CH N C
O
COCH
3
PY 106
2
X Y
Cl
NH N CH N C
O
COCH
3
PY 114
PY 126
PY 127
2
X
PY 152
Cl
NH N CH N C
O
COCH
3
2
H
5
C
2
O
foimulating high quality industiial fnishes). Table 78.7 gives a summaiy of the piopeities of the benz-
Figuie 78.20 illustiates the stiuctuie of the oiganic yellows that fall into the classifcation of benzimida-
stiuctuie as piesented in Figuie 78.21. In spite of the appaient degiee of complexity in the synthesis of
to fulfll the exacting demands of the consuming industiies. Compounds such as Isoindoline Yellow (PY
139) and Quinophthalone Yellow (PY 138) aie paiticulai examples of such complex, novel pigments.
All these yellows offei the usei additional high peifoimance pigments that fnd applications in high
piopeities of these heteiocyclic pigments.
TABLE 78.6 Summaiy of Diaiylide Yellow Piopeities
Coloui Index Name Common Name
a
Comments
PY 12 AAA Yellow Pooi lightfastness; pooi bleed iesistance; majoi use in piinting inks
PY 13 MX Yellow Reddei shade than PY 12; impioved heat stability and solvent fastness; majoi
use in piinting inks
PY 14 OT Yellow
(274-1744)
Gieen shade; some use in inteiioi fnishes; pooi tint lighfastness
PY 16 Yellow NCG Biight gieen shade; impioved heat and solvent fastness; used in full shade foi
coatings
PY 17 OA yellow
(275-0562)
Gieen shade; some use in inteiioi fnishes; pooi lightfastness
PY 55 PT Yellow Red shade; some use in inteiioi fnishes; pooi lightfastness; isomei of PY 14
PY 81 Yellow H10G Biight, gieen shade; same shade but much stiongei than PY 3
PY 83 Yellow HR
(275-0570)
(275-0050)
Veiy ied shade; impioved tianspaiency, heat stability, and lightfastness ovei PY
12; some use in inteiioi fnishes
PY 106 Yellow GGR Gieen shade; pooi tint lightfastness; majoi use in packaging inks
PY 113 Yellow H10G Veiy gieen shade; moie tianspaient than PY 12 and offeiing bettei heat and
solvent fastness; some inteiioi fnish use
PY 114 Yellow G3R Red shade; impioved solvent and lightfastness ovei PY 12; majoi use in oil-
based inks
PY 126 Yellow DGR Similai shade to PY 12 but offeiing impioved heat and solvent fastness; majoi
use in piinting inks
PY 127 Yellow GRL Biight, ied shade; pooi lightfastness; majoi use in offset inks
PY 152 Yellow YR Veiy ied, opaque pioduct; pooi lightfastness; some use in inteiioi fnishes as a
lead chiome ieplacement
a
Numbeis in paientheses aie codes used by Sun Chemical Coipoiation.
quality coatings, wheie the end use can justify the economics of puichasing. Table 78.8 summaiizes the
FIGURE 78.20 Benzimidazolone yellow stiuctuies.
TABLE 78.7 Summaiy of Benzimidazole Yellow Piopeities
Coloui Index Name Common Name Comments
PY 120 Yellow H2G Medium shade; good solvent fastness; excellent lightfastness; used in industiial
fnishes
PY 151 Yellow H4G Gieenei shade; good solvent fastness; excellent lightfastness; industiial and
iefnish applications
PY 154 Yellow H3G Gieen shade but ieddei than PY 151; good solvent fastness; excellent
lightfastness; industiial and automotive iefnish applications
PY 156 Yellow HLR Reddei shade; tianspaient; good exteiioi duiability in full shade and tint; all
exteiioi coatings and iefnish applications
PY 175 Yellow H6G Veiy gieen shade; good solvent fastness; excellent lightfastness; all exteiioi
coatings and iefnish applications
N N CH NH
C
C
O
O
O
COCH
3
H
3
COC
H
3
COC
NH
NH
O
P.Y. 120
N N CH NH
C
C
O
COCH
3
NH
NH
O
P.Y. 151
P.Y. 154
COOH
N N CH NH
C
C
O
O
COCH
3
NH
NH
O
CF
3
P.Y. 156 N N CH NH
C
C
COCH
3
NH
NH
O
Cl
Cl
O
P.Y. 175 N N CH NH
C
C
COCH
3
NH
NH
O
FIGURE 78.21 Stiuctuie of heteiocyclic yellows.
Cl
N N N
N
CH
C
C
O
C
6
H
5
CH
6
P.Y. 60
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
C
C
O
C
O
NH NH
N
C
N
CH
3
P.Y. 109
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
C
C
O
C
O
NH NH
N
C
N
P.Y. 110
P.Y. 138
Cl
Cl
Cl Cl
Cl Cl
Cl
Cl
C
O
CH
C
O
N
N
C C O O
P.Y. 139
N
C
C
C
C O
O
O
O
NH
NH
C
C
C
C O O
O
O
NH
NH
H
P.Y. 150
C
C
C
C O
O
O
NH
NH
N N C
C
C
C
O
O
NH
NH
O
Ni complex
TABLE 78.8 Summaiy of the Piopeities of the Heteiocyclic Yellows
Coloui Index Name Common Name/Desciiption Comments
PY 60 Aiylide Yellow Veiy ied shade; modeiate light and solvent fastness; tiade sales, latex
and masoniy paints; good acid and alkali fastness
PY 101 Methine Yellow Biight yellow; highly tianspaient and exceptionally biilliant;
industiial fnishes and specialty coatings; only modeiate bleed and
alkali fastness
PY 109 Tetiachloioisoindoline Gieen shade; excellent biightness stiength and duiability;
automotive fnishes
PY 117 Gieenish yellow complex
of an azomethine
Excellent chemical, light, and heat fastness; specialty fnishes
PY 129 Azomethine Yellow Veiy gieen shade; excellent oveiall fastness; industiial and specialty
coatings
PY 138 Gieen shade quinophthalone Clean hue and excellent oveiall fastness piopeities; high quality
industiial and automotive fnishes
PY 139 Red-shade isoindoline Similai in masstone to medium chiome (PY 34); excellent light and
solvent fastness; industiial and automotive coatings
PY 150 Pyiimidine Yellow Veiy gieen shade; good heat and lightfastness; industiial coatings
PY 153 Red-shade Nickel Dioxine Excellent fastness piopeities; specialty coatings and baking enamels;
pooi acid iesistance
PY 155 Azo Condensation Yellow Gieen shade; excellent oveiall fastness piopeities in full shade;
industiial and specialty coatings
PY 173 Isoindolone Yellow Veiy gieen shade; excellent fastness piopeities; industiial and
specialty fnishes
PY 182 Tiiazinyl Yellow Medium shade; excellent fastness piopeities at masstone levels;
industiial fnishes

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