Note: Descriptions are shown in the official language in which they were submitted.
` ~047~8~3
. . .
The invention provides useful novel azo pigments
~!i, of the formula
=N-CIH-CO~ ~o (1)
: H X CO~CH3 Z H
"'
wherein Q, X, Y and Z represent hydrogen or halogen atoms,
alkyl or alkoxy groups of 1 to 4 carbon atoms, aryl or aryl-
i,::
oxy groups which are unsubstitute~ or substituted by halogen
atoms or alkyl or alkoxy groups of 1 to 4 carbon atoms, and
wherein Q and X and Y and Z can a].so be closed via vicinal
.~ carbon atoms to form an isocyclic ring. The novel azo pig
;, .
'- 10 ments are obtained by coupling a diazo or diazoamino compound
of an amine of the formula
, .
~ NH2 (2)
"'
with an acetoacetic arylide of the formula
.
.:
' '
~ ,
-- 2 --
.. --.. . .. ... .
, , ~ . , , . . :
. . ~ :~ . : . . :
'.
'
1047488
. .
.-' ' y CIH3
: CH3C0-CH2C0~
~ . Z H
Azo pigments having a particularly interesting
. utility are those of the formula (1) wherein Q, X, Y and Z
represent hydrogen or chlorine atoms, methyl, ethyl, methoxy,
~ 5 ethoxy, phenyl or phenoxy groups, especially those of the
formula
~ N C0-CH3 H
,. . .
. wherein Xl and Yl represent hydrogen or chlorine atoms, me-
thyl, ethyl, methoxy, ethoxy groups or phenyl or phenoxy
groups which are unsubstituted or substituted by 1 or 2
; chlorine atoms or methyl groups.
The colourant of the formula
CH3 ~ CH3
; ~ o CH30 ~ ~ (5)
H C0-CH3 H
3 -
.
, - - ' .'
~, -. : . .: : .
-- ~ :. :
, - , . .
.:
. . ~ . .
.
10~7~88
is characterised by particularly good properties.
As diazo components there are preferably used those
of the formula (2~, wherein e and X represent hydrogen or
chlorine atoms, methyl, ethyl, methoxy, ethoxy groups or
phenyl or phenoxy groups which are unsubstituted or substitu-
ted by 1 or 2 chlorine atoms or by methyl groups.
Examples of diazo components are:
4-methyl-6-phenoxy-7-amino-quinolone-(2)
4-methyl-6-chloro-7-amino-quinolone-(2)
4-methyl-6-methoxy-7-amino-quinolone-(2)
4,6-dimethyl-7-amino-quinolone-(2)
; ~
4-methyl-7-amino-quinolone-(2)
4-methyl-7-chloro-6-amino-quinolone-~2)
4,8-dimethyl-7-amino-quinolone-(2)
There are preferably used as coupling components
- acetoacetic arylides of the formula (3), wherein Y and Z re-
present hydrogen or chlorine atoms, methyl, ethyl, methoxy,
ethoxy groups or phenyl or phenoxy groups which are unsub-
stituted or substituted by 1 or 2 chlorine atoms or by me-
thyl groups.
Examples of coupling components are:
4-methyl-6-methoxy-7-acetoacetylamino-quinolone-(2)
4-methyl-6-chloro-7-acetoacetylamino-quinolone-(2)
4-methyl-7-chloro-6-acetoacetylamino-quinolone-(2)
, .
,
..
' : .~ : . ~ .
.
,
. ' ' - '
~047488 i
4,8-dimethyl-7-acetoacetylamino-quinolone-(2)
4-methyl-7-acetoacetylamino-quinolone-(2)
4,6-dimethyl-7-acetoacetylamino-quinolone-(2)
4-methyl-6-phenoxy-7-acetoacetylamino-quinolone-(2).
The acetoacetic arylides to be used according to
the invention are obtained, for example, by addition of di- ~-
ketone to the amino-quinolones-(2).
The coupling is normally effected by gradually
, adding the acid solution of the diazonium salt to the aqueous
r~ 10 alkaline or aqueous acetic acid solution or also aqueous
acetic acid suspension of the coupling component or its solu-
tion in an organic water-immiscible solvent, desirably at a
pH of 4 to 7.
It is advantageous to adjust the pH by addition of
a buffer. Examples of suitable buffers are the salts, espe-
cially alkaline salts, of formic acid, phosphoric acid or,
in particular, of acetic acid. The alkaline solution of the
coupling component desirably contains a wetting agent, a
; dispersant or an emulsifier, for example an aralkylsulphonate,such as dodecylbenzenesulphonate or the sodium sa]t of 1,1'-
~` dinaphthylmethanesulphonic acid, polycondensation products
of alkylene oxides, for example the reaction product of ethy-
lene oxide and p-tert. octylphenyl, also alkyl esters of sul-
phoricinoleates, for example n-butylsulphoricinoleate. The
_
,
,' . ~ ', ':. ': -
: ~
- , . . .. .
. .
,
' '' ,' ': , ' ; '
, ' ' ' , .
1~47488
dispersion of the coupling component can also contain with
advantage protective colloids, for example methyl cellulose
, or small amounts of inert organic solvents which are spar-
ingly soluble or insoluble in water, for example aromatic
hydrocarbons which may be halogenated or nitrated, such as
benzene, toluene, xylene, chlorobenzene, dichlorobenzene o
nitrobenzene, as well as aliphatic halogenated hydrocarbons,
; for example carbon tetrachloride or trichloroethylene, also
water-miscible organic solvents, such as acetone, methyl
ethyl ketone, methanol, ethanol or isopropanol, especially
, dimethyl formamide.
It is also possible to carry out the coupling with
advantage by continuously combining an acid solution of the
diazonium salt with an alkaline solution of the coupling
component in a mixing jet so as to effect an immediate coup-
ling of the components. The resultant colourant dispersant
is continually drawn off from the mixing jet and the colour-
ant isolated by filtration.
Instead of using the diazonium salt it is also
possible ~o use the corresponding diazoamino compounds. These
are obtained by a known method by coupling an aryldiazonium
salt with a primary or preferably with a sécondary amine.
Amines of the most diverse kinds are suitable for this pur-
pose, for example aliphatic amines, such as methylamine,
ethylamine, ethanolamine, propylamine, butylamine, hexylamine
~ ....... . . ....
.
. .
- ' ~ . . . " ' '
047488
and especially dimethylamine, diethylamine, diethanolamine,
methylethanolamine, dipropylamine or dibutylamine, amino-
acetic acid, methylaminoacetic acid, butylaminoacetic acid,
aminoethanesulphonic acid, methylaminoethanesulphonic acid,
guanylethanesulphonic acid, ~-aminoethylsulphuric acid, ali-
. . ~
cyclic amines, such as cyclohexylamine, N-methylcyclohexyl-
amine, dicyclohexylamine, aromatic amines, such as 4-amino-
benzoic acid, sulphanilic acid, 4-sulpho-2-aminobenzoic acid,
(4-sulphophenyl)-guanidine, 4-N-methylaminobenzoic acid, 4-
ethylaminobenzoic acid, 1-amino-naphthalene-4-sulphonic acid,
l-aminonaphthalene-2,4-disulphonic acid, heterocyclic amines,
such as piperidine, morpholine, pyrrolidine, dihydroindole,
i and finally also sodium cyanamide or dicyandiamide.
,' As a rule, the diazoamino compounds obtained are
~ 15 sparingly soluble in water and can be isolated from the reac-
,
tion medium in crystallised form, if appropriate after they
~: have been salted out. In many instances the moist press
cakes can be used for the further reaction. In individual
cases it may prove desirable to dehydrate the diazoamides be-
fore the reaction by means of vacuum drying.
The coupling of the diazoamino compound with the
coupling component takes place in an organic solvent, for
example chlorobenzene, o-dichlorobenzene, nitrobenzene, py-
ridine, ethylene glycol, ethylene glycol monoethyl or mono-
-- 7 --
........... . .
, : ~ - --- .. _ .
,
.
~047488
methyl ether, dimethyl formamicle, formic acid or acetic acid.
When using water-miscible solvents it is not necessary to
use the diazoamino compounds in anhydrous form. The aqueous
moist filter cakes may be used, for example.
Finally, the coupling can also be effected by sus-
pending the amine with the coupling component in the ratio
1:1 in an organic solvent and treating the resultant suspen-
sion with a diazotising agent, especially with an ester of
nitric acid, such as methyl, ethyl, butyl, amyl or actyl
nitrite.
On account of their insolubility, the resultant
pigments can be isolated from the reaction mixture by fil-
- tering them off. Since the by-products remain in solution,
the pigments are obtained in outstanding purity. It is ex-
pedient to subject the pigments, especially those obtained
by the aqueous coupling method, to an aftertreatment with
organic solvents. This is accomplished by heating the re-
sultant crude pigments in an inert organic solvent, for ex-
ample methylene glycol monomethyl ether, ethylene glycol
monomethyl ether, dimethyl formamide, N-methylpyrrolidone,
monochloro- or dichlorobenzene, toluene, xylene or nitro-
-~ benzene, after which treatment they are obtained in the form
of soft-grained powders.
The colourants constitute productive and pure pig-
" . , . : . - . - : - , . .
- . . . . . ~ :
~' ' '' ,' . . ' . ' . ~, ~ . -'
. ~ . '
~ " ':
.
.
i,i~,
1047~8
- ments which, on account of their favourable properties, such
as fastness to migration and light, can be used for the most
diverse kinds of pigment application. They are eminently
suitable for use in the printing ink industry and also for
' 5 pigmenting organic material of high molecular weight, for
example cellulose ethers and esters, polyamides and polyur-
ethanes or polyesters, acetyl cellulose, nitrocellulose, na-
tural or synthetic resins, such as polymerisation or conden-
sation resins, for example aminoplasts, especially urea/
formaldehyde and melamine/formaldehyde resins, alkyd resins,
phenolic plastics, polycarbonates, polyolefins, such as poly-
styrene, polyvinyl chloride, polyethylene, polypropylene,
polyacryloDitrile, polyacrylic ester, rubber, casein, silicon
,
and silicone resins, individually or in mixtures.
t~ 15 It is immaterial whether the cited compounds of
high molecular weight are in the form of plastics, melts or
spinning solutions, paints or lacquers or printing inks.
~ Depending on the use to which they are put, it is advantage-
t`'`~ ' OUS to~use the novel pigments as toners or in the form of
preparations.
The resultant colourations are characterised by
good general fastness properties, especially by good fastness
to light, migration and overstripe bleeding.
The following Examples illustrate the invention,
.
~ 04748~3
:.-
the parts and percentages being by weight unless otherwise
: stated.
`:
`~
,, .
' , .
.'
~'.' ' :
'
.
. ' . ,
- 10 -
-:
.. _ ~_ . . . . .
, - . , . - , . .
,. . - . - , . . , ~- . .
' . ~ . ' ,' '
.
~0~7'}88
Example 1
, i
j:
. .
While cooling with ice, 2.66 parts of 4-methyl-6-phenoxy-7-
~- amino-quinolone-(2) are diazotised in the usual manner in
,, ,
100 parts of water with 2.5 parts by volume~of 10 normal hy-
drochloric acid and 2.5 parts of 4 normal sodium nitrite
i~,
solution. The diazo solution is clarified by filtration.
- 2.88 parts of 4-methyl-6-methoxy-7-acetoacetylaminoquinolone-
(2) are added to 200 parts by volume of dimethyl formamide.
After 3 parts of anhydrous sodium acetate have been added,
the above diazo solution is poured in over c. 2 mim~tes.
;. The coupling mixture is stirred for several hours at room
temperature and the pigment which has formed is filtered off,
washed with hot water and methanol and dried. The product is
obtained as a brown, hard-grained substance which retains its
colouristically useful form by treating it in boiling N-me-
thylpyrrolidone over the course of half an hours. After it
has been isolated at room temperature, washed with methanol
and dried, the pigment is a soft-grained yellow powder which
colours polyvinyl chloride in a yellow shade which is fast
to light and migration and has the formula
.
- 11 -
.
`~ 1047488
.
~ ;3 ~ O ~ H3CO
.. l H O-CH3
~ The Table lists further pigments which are obtained by the
.
same procedure by coupling the diazo compound of the amine
indicated in column I with the coupling component indicated
in column II. Column III indicates the shade of the resul-
~: tant pigment dye in polyvinyl chloride.
,: ~
. .
., .
~, ~
,~,
", , .
- 12 -
. .
, ' ,, ', ' .
,:
:
04748~
_ _ II IIT
. 2 4-methyl-6-chloro- 4-methyl-7-chloro-6- yellow
7-amino-quinolone- acetoacetylamino-
. (2) quinolone-(2)
,, . .. .
y 3 4-methyl-6-methoxy- 4-methyl-7-chloro-6- reddish
7-amino-quinolone- acetoacetylamino- yellow
. (2) quinolone-(2)
'.' _ ,
4 4,6-dimethyl-7- 4-methyl-7-chloro-6- yellow
. amino-quinolone-(2) acetoacetylamino-
quinolone-(2)
., _ .
. 5 4-methyl-7-amino- 4-methyl-7-chloro-6- greenish
:~ quinolone-(2) acetoacetylamino- yellow
.~ quinolone-(2)
.
. 6 4-methyl-7-chloro- 4-methyl-7-chloro-6- reddish
6-amino-quinolone- acetoacetylamino- yellow
(2) quinolone-(2)
. .
: 7 4,8-dimethyl-7- 4-methyl-7-chloro-6- yellow
amino-quinolone-(2) acetoacetylamino-
. quinolone-(2)
.'i, .. _ ..
. 8 4-methyl-7-amino- 4-methyl-6-chloro-7- greenish
quinolone-(2) acetoacetylamino- yellow
. . quinolone-(2)
, .. _ --'-'I
. 9 4,6-dimethyl-7- 4-methyl-6-chloro-7- yellow
. amino-quinolone-(2) acetoacetylamino-
. . quinolone-(2)
,
: 10 4,8-dimethyl-7- 4-methyl-6-chloro-7- greenish
amino-quinolone-(2) acetoacetylamino- yellow
. _ _ quinolone-(2)
_ 13 -
~04748~
.
:,~ _
. I II III
,
11 4-methyl-6-methoxy- 4-methyl-6-chloro-7- yellow
7-amino-quinolone- acetoacetylamino-
. (2) quinolone-(2)
~ 12 4-methyl-5-phenoxy- 4-methyl-6-chloro-7- greenish
.: 7-amino-quinolone- acetoacetylamino- yellow
~ (2) quinolone-(2)
,, .
13 4-methyl-6-chloro- 4-methyl-6-chloro-7- greenish
7-amino-quinolone- acetoacetylamino- yellow
(2) quinolone-(2)
. 14 4-methyl-7-chloro- 4-methyl-6-chloro-7- greenish
6-amino-quinolone- acetoacetylamino- yellow
(2) quinolone-(2)
_ . _ . .
: . 15 4-methyl-7-amino- 4,8-dimethyl-7-aceto- greenish
-: quinolone-(2) acetylamino-quinolone- yellow :
_ . _ .
: 16 4,6-dimethyl-7- 4,8-dimethyl-7-aceto- reddisn
amino-quinolone-(2) acetylamino-quinolone- yellow
,' . .
:. 17 4,8-dimethyl-7- 4,8-dimethyl-7-aceto- yellow
amino-quinolone-(2) acetylamino-quinolone-
. 18 4-methyl-6-methoxy- 4,8-dimethyl-7-aceto- orange
. . 7-amino-quinolone- acetylamino-quinolone-
'.' _ ................ .. ... _ I ....
19 4-methyl-6-phenoxy- 4,8-dimethyl-7-aceto- greenish
_ .. _ _ . aceeylamino-quinolone- yell~
:
- 14 -
,. .... .. . .
- -, - : . . . .
'- : :, .
. : . : : ' :. ':
: . .
'',- ~ '
- ,
~! ~0 47 4 81~
. _ II III ~
,.,'
. 20 4-methyl-6-chloro- 4,8-dimethyl-7-aceto- yellow
_ 7-amino-quinolone- acetylamino-quinolone-
21 4-methyl-7-chloro- 4,8-dimethyl-7-aceto- reddish
6-amino-quinolone- acetylamino-quinolone-
22 4-methyl-7-amino- 4-methyl-7-aceto- greenish
quinolone-(2) ace~ylamino~quinolone- ycll~w
23 4,6-dimethyl-7- 4-methyl-7-aceto- reddish
amino-quinolone-(2) acetylamino-quinolone- ~1l~
24 4-methyl-6-methoxy- 4-methyl-7-aceto- reddish
_ 7-amino-quinolone- acetylamino-quinolone-
. 25 4-methyl-6-phenoxy- 4-methyl-7-aceto- greenisn
7-amino-quLnolone- acetylamino-quinolone- Y-llc~
26 4-methyl-6-chloro- 4-methyl-7-aceto- yellow
7-amino-quinolone- acetylamino-quinolone-
27 4-methyl-7-chloro- 4-methyl-7-aceto- reddish
6-amino-quinolone- acetylamino-quinolone- y~
. 28 4-methyl-7-amino- 4,6-dimethyl-7-aceto- greenish
. _ quinolone-(2) acetylamino-quinolone- ye IIA~
,...
~ .
1047488
:
I II III
29 4,8-dimethyl-7- 4,6-dimethyl-7-aceto- greenish
amino-quinolone-(2) acetylamino-quinolone- yellow
(2)
_ ...~ ... .
4-methyl-6-methoxy- 4,6-dimethyl-7-acèto- reddish
7-amino-quinolone- acetylamino-quinolone- yellow
,~ .. _
31 4-methyl-6-phenoxy- 4,6-dimethyl-7-aceto- greenish
-: 7-amino-quinolone- acetylamino-quinolone- yellow
. (2) (2)
_ _ .
; 32 4-methyl-6-chloro- 4,6-dimethyl-7-aceto- greenish
: 7-amino-quinolone- acetylamino-quinolone- yellow
. (2) (2)
,'. _
.- 33 4-methyl-7-amino- 4-methyl-6-phenoxy-7- greenish
~: quinolone-(2) acetoacetylamino- yellow
~, quinolone-(2)
, _ ._ _ .'
34 4,6-dimethyl-7- 4-methyl-6-phenoxy-7- greenish
amino-quinolone-(2) acetoacetylamino- yellow
.: quinolone-(2) : .
, _ .
;~ 35 4-methyl-6-methoxy- 4-methyl-6-phenoxy-7- yellow
. 7-amino-quinolone- acetoacetylamino-
(2) quinolone-(2)
.
36 4-methyl-6-phenoxy- 4-methyl-6-phenoxy-7- greenish
. 7-amino-quinolone- acetoacetylamino- yellow
; (2) quinolone-(2)
37 4-methyl-6-chloro- 4-methyl-6-phenoxy-7- greenish
7-amino-quinolone- acetoacetylamino- yellow
_ _ i quinolone-(2)
_ 16 -
.: , . ~ , . ' ,,
.. ..
,
: ,
,.
r
~0474~8
; II III
.,
38 4-methyl-7-chloro- 4-methyl-6-phenoxy-7- yellow
: 6-amino-quinolone- acetoacetylamino-
. (2) quinolone-(2)
. , .
. 39 4-methyl-7-amino- 4-methyl-6-methox~-7- yellow
quinolone-(2) acetoacetylamino-
.. quinolone-(2)
.
40 4,6-dimethyl-7- 4-methyl-6-methoxy-7- greenish
amino-quinolone-(2) acetoacetylamino- yellow
. quinolone-(2)
" _ .
..41 4,8-dimethyl-7- 4-methyl-6-methoxy-7- greenish
..amino-quinolone-(2) acetoacetylamino- yellow
'7,'" quinolone-(2)
~" _ . ........ _ ............. .. _
. 42 4-methyl-6-methoxy- 4-methyl-6-methoxy-7- yellow- 7-amino-quinolone- acetoacetylamino-
.,: (2) quinolone-(2)
. ...
t~'-
.. 43 4-methyl-6-chloro- 4-methyl-6-methoxy-7- yellow
. 7-amino-quinolone- acetoacetylamino-
. (2) quinolone-(2)
,.~ _ . ................ _ ~_
. 44 4-methyl-7-chloro- 4-methyl-6-methoxy-7- greenish
: 6-amino-quinolone acetoacetylamino- yellow
(2) quinolone-(2)
:~ . - --I
45 4-methyl-6-phenoxy- 4-methyl-7-chloro-6- yellow
. 7-amino-quinolone- acetoacetylamino-
(2) quinolone-(2)
.. . __ ..
~- 46 4-methyl-6-(4' 4-methyl-7-acetoacetyl- yellow
chlorophenoxy)-7- amino-quinolone-(2)
_ amino-quinolone-(2) .
- 17 -
,~ . .
10474E~8
,:
. II III
:. ..
47 ¦ -methyl-6-(4' 4,6-dimethyl-7-aceto- greenish
chlorophenoxy)-7- acetylamino-quinolone- yellow
':. amino-quinolone-(2) (2)
~ ' .
. 48 4-methyl-6-(4' 4,8-dimethyl-7-aceto- greenish
: chlorophenoxy)-7- acetylamino-quinolone- yellow
amino-quinolone-(2) (2)
~;`
.~ 49 4-methyl-6-(4' 4-methyl-6-methoxy-7- yellow
. chlorophenoxy)-7- acetoacetylamino-quino-
.. amino-quinolone-(2) lone-(2)
_ .. _
-.- 50 -methyl-6-(4' 4-methyl-6-phenoxy-7- greenish
chlorophenoxy)-7- acetoacetylamino-quino- yellow
. amino-quinolone-(2) lone-(2)
".' ....
- 51 4-methyl-6-(4' 4-methyl-6-chloro-7- greenish
... chlorophenoxy)-7- acetoacetylamino-quino- yellow
amino-quinolone-(2) lone-(2)
.. ...__
. 52 4-methyl-6-(4' 4-methyl-7-chloro-8- greenish
chlorophenoxy)-7- acetoacetylamino-quino- yellow
amino-quinolone-(2) lone-(2)
' ....
53 1 -methyl-6-(4' 4-methyl-7-chloro-8- greenish
hlorophenoxy)-7- acetoacetylamino-quino- yellow
. l mino-quinolone-(2) lone-(2)
_ .. _
54 ¦ ,5,8-trimethyl-6- 4-methyl-7-acetoacetyl- yellow
l mino-quinolone-(2) amino-quinolone-(2)
_
¦ ,5,8-trimethyl-6- 4,6-dimethyl-7-acetoace- yellow
3mino-quinolone-(2) tylamino-quinolone-(2)
_ 18 ~
, , . - , , - -
-- . ' - '
'. ' - ' - ' ' '
, ~, ~ ,
,
1047~
I II III
.. ._
. 56 4,5,8-trimethyl-6- 4,8-dimethyl-7-aceto- reddish
amino-quinolone-(2) acetylamino-quinolone- yellow
. 57 4,5-dimethyl-8- 4,8-dimethyl-7-aceto- reddish
: methoxy-6-amino- acetylamino-quinolone- yellow
~ quinolone-(2) (2)
,,
58 4,5-~imethyl-8- 4-methyl-6-phenoxy-7- yellow
. methoxy-6-amino- acetoacetylamino-quino-
quinolone-(2) lone-(2)
~.
59 4-methyl-5,8-dime- 4-methyl-6-phenoxy-7- yellow
thoxy-6-amino- acetoacetylamino-quino-
quinolone-(2) lone-(2)
.,
. 60 4-methyl-6-amino- 4-methyl-6-phenoxy-7- yellow
. 7,8-benzo-quinolone- acetoacetylamino-quino-
. (2) lone-(2)
~. ._._
61 4-methyl-6-amino- 4-methyl-6-chloro-7- orange
.~ 7,8-benzo-quinolone- acetoacetylamino-quino-
(2) lone-(2)
,. _
62 4-methyl-6-amino- 4-methyl-7-chloro-6- orange
7,8-benzo-quinolone- acetoacetylamino-quino-
(2) lone-(2)
_ _
63 4-methyl-5,8-di- 4,8-dimethyl-7-acetoace- reddish
etho~y-6-amino- tylamino-quinolone-(2~ yellow
: _ quinolone-(2) .
.
- 19 -
1047~
Example 64
, :
65 parts of stabilised polyvinyl chloride, 35 parts of di-
octyl phthalate and 0.2 parts of the colourant obtained ac-
cording to Example 1 are stirred together and the mixture
is then rolled to and from ~r 7 minutes at 140C on a two-
roll calender to yield a yellow sheet of good fastness to
light and migration.
s
. . .
, .
Example 65
1 g of the pigment obtained according to Example 1 and 4 g
of the litho varnish of the foll~wing composition
- 29,4% of linseed oil/stand oil (300 poise)
67.2% of linseed oil/stand oil (20 poise)
2,1% of cobalt octoate (8% Co) and
1.3% of lead octoate (24% Pb)
are finely ground in an Engelsmann grinder and subsequently
printed on art paper using a block by the letterpress print-
ing method (application of 1 g/m2). A strong, bright, orange
yellow shade of good transparency and good gloss is obtained.
Very brilliant green shades can be obtained in three or four
' ' , ' .
,, .
. .
- . '. ' .
,': 1047488
colour printing by overprinting on blue.
. The pigment is also suitable for other printing methods,
for example intaglio printing, offset printing, flexographic
printing, whereby equally good results are obtained.
~,
,...
`:
- 21 -
: .
