Note: Descriptions are shown in the official language in which they were submitted.
~a~4S12~
The present invention relates -to valuable, new disazo
pigments o -the formula
.
R2 ~ ~ 3 R (I)
L 1 .
'`'' "
~herein Rl denotes a H atom, an alkyl group which contains
1-4 C atoms and is optionally substituted by a phenyl radical, '~
or an aryl rad.ical, particularly a phenyl radical which is
optionally substituted by halogen a-toms or alkyl or alkoxy
groups containing 1-4 C atoms, R2 denotes a H atom, an a].kyl
group containing 1-~ C atoms, a cyano or car.barnoyl gr~up, or
an alkanoylamino group containing 2-4 C atoms, R3 denotes an
alkyl group containing 1-4 C atoms, an alkoxycarbonyl group c~l- :
taining 2~6 C atoms or a phenyl group which is optionally .
substituted by halogen atoms or alkyl or alkoxy groups Gon- ..
taining 1-4 C atoms, Z denotes anO atom, or a N atom which ;-
conjointly with the radical R1 forms a benzimidazole ring,
X and Y denote H or halogen atoms, or methyl or nitro groups
and V denotes anO atom or a ~CO- group.
Ihe pig.nents of the ~ormula
, '~
- .
':
1~45~LZ(~
OH ~ - O HO ~Y ~,z (II)
CN
or
z ~ lo/ ~3 ~ CN
p O R3
., wherein Rl, R3 and Z have the meaning in~icated above, are
j of particular in-terest.
~' The new disazo pigments are obtained if the -tetrazo
i compound of a diamine of the formula
H2~
: is coupled, in a molar ratio of 1:2~ with a pyridine deriva-
tive of the formula ~-
R3
R2 (V) ;~ ~'
HO Z
: ~ L
~ 3 ~
-
"
104~2
'1,5-Dlaminoanthraquinone and 2,6~diaminoanthriaauinorle
are of particular interest as the diamines.
The following further diamines should be mentioned:
4,8-dinitro-1,5-diaminoa~thraq~linone, 2,6-dimethyl-1,5-diamino-
anthraquinone, 2,~-dibromo-1,5-diaminoanthraquinone~ 1,6~
diaminoanthraqui1lone 5 1,7-diaminoan-thraquinone, 1,5-dichloro-
2,6~diaminoanthraquinone, 3,7--dibromo-2,6-diaminoanthraquinone,
1,3,5,7-tetrabrorno-2,5-diarninoanthraquinone, 1,5-dinitro~2,6
diaminoanthraquinone, 2,4,6,8-tetrachloro-1,5-diaminoanlhra -~
quinone, 2,4,6,8 tetrabromo-1~5--diaminoanthraquinone, 1,5-
dibromo-2,6-diaminoanthraquinone, 3,7-dibromo-2,6--diamil~o
anthraquinone, 3,6-dibromo-2,7-diaminoanthraquinone and
finally 2,6-diaminoxan-thone and 3 methyl--2,6-diaminoxanthone,
The coupling components pre~erably correspond to the
formula
~R3
~ N (V13
- HO ~ Z
Rl `
wherein Rl, R3 and Z have the meaning lndicated.
Particular interest attaches to pyridine derivatives
of the formulae 3
~ N UO
HO (VII) ~ (VII'L) ~
Rl Xl ~1. ''
- . . ,.:
~ '' ' .
109LS~2~
wherei.n ~1 ard R3 have the m.eani.ng indicated and preferably
denote a me-thyl or phenyl group, and Xl and Y1 denote H or
halo~en atoms, ni-tro or carbamoyl groups, alkyl, alkox~- or
alkylsulphonyl ~roups containing 1~4 C atoms, alkoxycarbonyl,
alkanoylamino or alkylcarbamoyl groups con-taining 2-6 C atoms,
or phenox~- or phenylcarbamoyl groups which are optiona~lly
substituted by halogen atoms or alkyl or alkoxy groups con~
taining 1--4 C atoms.
The pyridones of the ~ormula (VII) are known compo~nds,
The following examples should be mentioned: 4~methyl-3-cyano
6-hydroxypyrid-2-one, 1 methyl-3-cyano-4~methyl-6-hydroxy-
pyrid-2 one, 1-ethyl-3~cyano-4~methyl-6-hydroxypyrid~2-one,
l~phenyl-3-cyano-4-methyl-6-hydroxypyrid-2-on.e, 1-p--tolyl-3-
cyano~4 methyl 6-hydroxypyrid~2 one, l~p-anisyl-3-cyano-4-
methyl-6-hydroxypyrid-2-one, 1-phenyl-3-cyano-4-phenyl-6- .,
hydroxypyrid-2-one, 1-p-tolyl-3-cyano-4-phenyl-6~hydroxypyrid
2-one, 1-p-anisyl-3-cyano-4-phenyl-6-hydroxypyrid-2-one, 1-
phenyl-3-carbonamido-4-methyl-6-hydroxypyrid-2-one, 1 phenyl_
3-carbonamido-4-phenyl-6-hydroxypyrid~2-one, 2,6-dihydroxy~-3
~yano-4-ethoxycarbonylpyridine, 2,6-dihydroxy-4~methylpyridine, .
2,6~dihydroxy-4-phenylpyridine, 2,6-dihydroxy~4-(p-methoxy--
phenyl)-pyridine, 4-methyl-2,6-dihydroxypyridine, 1-ethyl-4- :
methyl-3~ace-tylamino-6-hydroxypyrid-2-one, 1,4-dimethyl-3~
acetylamino-6-hydroxypyrid-2-one, 1-ethyl~4-phenyl-3-acetyl- -
amino-6-hydroxypyrid-2-one and 1-phenyl-4 methyl-3-acetyl-
amino-6-hydroxypyrld-2-one. .`
The benzimidazolopyridines are appropriately obtained by ;
.
_ 5 ~ .-,:
' ;'
:~ `
~ 04S~
kno~ ~rocesses by condensation of a benzimidazole o. the
formula
X1 H
~- C1~2~R2 ,~ ,
~1 . '
- wherein R2, Xl and Yl have -the mean.ing indicated, ~ith an
acylacetic ester o~ the formula
'.
~jCOCH2COOR . . ' .
:,
wherein R denotes an alkyl group containing 1-4 C atoms, and
R3 has the meaning indicated.
The follo~.Ting examples of acylacetic esters should be
mentioned: acetaacetic acid methyl ester, acetoacetic acid
ethyl ester, benzoylacetic acid ethyl ester and oxalacetic
acid diethyl ester
The following benzimidazoles should be mentioned: 2-
cyanomethyl-benzimidazole, 2-cyanomethyl-4-chloro-benzimidazole,
2-cyanomiethyl-5-chloro-benzimidazole, 2-cyanomethyl-5,6-
dichloro-benzimidazole, 2-cyanomethyl-4 chloro-6-methyl~
benzimidazole, 2-cyanomethyl-5-methoxy-benzimidazole, 2~cyano
me-thyl-6~ethoxy-benzimidazole, 2-cyanomethyl 6-nitro~benzimida~
zole, 2-cyanomethyl-5~methylsulphonyl-benzimidazole, benzimida~
zolyl-2-acetic acid amide, 2-ethyl-benzimidazole and 2-cyano-
methyl-5-tri~Dluoromelhyl-benzlm.idazo].e. ,
The coupling is appropriately carrled out by adding the
~, .
6 --
lO~S~
tetrazohium solutiGn gradually to an aqueous or organic solu-
-tion of the coupling component~ at a pH value of 4-8 It
is advantageous to adjust the pH value by adding a buffer
Examples o~ buffers which can be used are the salts, particular-
ly alkali metal salts, of formic acid, acetic acid or phos-
phoric acid and tertiary nitrogen bases3 such as pyridine,
trimethylamine, triethylamine or triethanolamine
Furthermore, wetting, dispersing or emulsifying agents~ for
example an aralkylsulphona~e, such as dodecylbenzenesulphona-te~
polycondensation products of ethylene oxides, such as the
product of the reaction of ethylene oxide with p-tert -octyl-
phenol, and also alkyl esters of sulphoricinoleates, for
example n-butyl-sulphoricinoleate, can be added to the coupling ::
solution The coupling dispersion can also con-tain pro-
tective colloids, for example methylcellulose or minor amounts
of an inert organic solvent which is sparingly soluble or
insoluble in water, for example halogenated or nitrated
aromatic hydrocarbons, such as benzene, toluene, xylene,
chlorobenzene, dichlorobenzene or nitrobenzene, and aliphatic :
halogenohydrocarbons, such as carbon tetrachloride or tri- .
chloroethylene, and also organic solvents ~ihich are miscible
with water, such as acetone, methanol, ethanol, isopropanol,
methyl ethyl ketone and dimethylformamide. -
By virtue of their insolubility, the resulting pigments
can be isolated from the reaction mixtures by filtration.
An after-treatment in an organic solvent, preferably a solvent .
boiling above 100C generally proves advantageous in order to
~ ' ', . :
: - 7 - .
~, .
.' ,. :
~0 ~ 5
obtain an excellent texture of these pigments. Solvents
~rhich are found to be particularly suitable are benzene deriva-
tives substituted by ~alogen atoms or alkyl or nitro groups,
such as xylene, chlorobenzene 5 o-dichlorobenzene or nitro-
benzene, and pyridine bases, such as pyridlne, picoline or
quinoline, and also ketones, such as cyclohexanone, ethers,
such as ethylene glycol monomethyl ether or ethylene glycol
monoethyl ether, amides, such as dimethylformamide, dimethyl-
acetamide or N-methylpyrrolidone, and sulphoxane. m e
- after-treatment is preferably carried out by heating the dried
pigment in the solvent to 100-150C, in the course of which a `-
homogeneous crystal structure is formed and, in many cases,
there is a coarsening o~ grain, which has a ~a*ourable effect
on the rheological behaviour and on the ~astness to migration
and light of the resulting pigments.
The coupling can also be carried out advantageously by
adding an acid solution o~ the tetrazonium salt slowly to an
organic solution, buffered with a tertiary nitrogen base~ of
the coupling component Suitable organic solvents are,
in particular, water-miscible solvents, such as dimethylforma-
mide, dimethylacetamide, N-methylpyrrolidone and dimethyl-
sulphoxide or sulphoxone. This method of~ers the
advantage that, after the coupling is completed, water and
readily volatile solvents which have been added with the
tetrazo component, can be distilled o~f and the after-treat-
ment can be carried out in the coupling suspension
The coupling can also be carried out by continuously
- 8 - ~
, .
' ' . ....
1(~4~L%O
combining, in a mixing jet, an acid solution of the tetrazon-
- ium sal-t with an alkaline solution of the coupling component,
in the course o~ which an immediate coupling of the components
takes place. The resulting colorant suspension is
continuously withdrawn from the mixing jet and the colorant
is isolated by ~iltration.
- Instead o~ the tetrazonium salts, it is also possible
to use the corresponding tetraZOaminO compounds~ These
are obtained by a known process by coupling an aryltetrazonium
salt with 2 mols of a primary, or preferably a secondary,
amine. The most diverse amines are suitable ~or this
purpose, ~or example aliphatic amines, such as methylamine,
ethylamine, ethanolamine, propylamine, butylamine, hexylamine
- and, particularly, dimethylamine, diethylamine, diethanolamine,
methylethanolamine, dipropylamine or dibutylamine, aminoacetic -
acid, methylaminoacelic acid, butylaminoacetic acid, amino- -
ethanesulphonic acid, methylaminoethanesulphonic acid, guanyl-
ethanesulphonic acid or ~-aminoethylsulphuric acid, alicyclic
amines, such as cyclohexylamine, N-methylcyclohexylamine or
dicyclohexylamine, aromatlc amines, such as 4-aminobenzoic
acid, sulphanilic acid, 4-sulpho-2-aminobenzoic acid, (4-
~sulphophenyl)-guanidine, 4-N-methylaminobenzoic acid, 4-
ethylaminobenzoic acid, l-aminonaphthalene-4-sulphonic acid or
l-aminonaphthalene-2,4 disulphonic acid, heterooycllc amines,
such as piperidine, morpholine, pyrrolidine or dihydroindole,
~; ~ and finally also sodium cyanamide or dicyandiamide.
As a rule, the resulting tetrazoamino compounds are
:
~ ~ - 9
1~5~0
sparingly soluble in cold water and can, if appropriate, be
isolated from the reaction medium in a crystalline form a~ter
salting out In many cases the moist press cakes can
be used for a further reaction. In individual cases it
can be found appropriate to free the tetrazoamides from
water by vacuum drying, prior to the reaction.
The coupling of the tetrazoamino compound with the -
coupling component is carried out in an organic solvent, for
example chlorobenzene, o-dichlorobenzene, nitrobenzene,
pyridine, ethylene glycol, ethylene glycol monoethyl or mono-
methyl ether, dimethylformamide, formic acid or acetic acid.
When solvents,which are miscible with water,are used, it is
not necessary to use the tetraZOaminO compounds in an
anhydrous form. ~or example, filter cakes which are ;~
moist with water can be used.
The coupling is appropriately carried out in a warm,
acid medium, preferably at temperatures between 80 and 180C,
and generally proceeds very rapidly and to completion I~
neutral solvents are used, it is advantageous to add an acid,
for example hydrogen chloride, sulphuric acidg formic acid or !,
acetic acid. By virtue of their insolubility, the
resulting pigments can be isolated from the reaction mixturè
by ~iltration It is, therefore, unnecessary in most
cases to carry out an after-treatment with organic solvents,
such as is required in the case of pigments which are obtained
by the aqueous coupling route
Finally, the coupling can also be accomplished by
- 10 - .`
- ~ , . : .
':
`
10~5~l2(~
suspending the diamine to be tetrazotised in an organic sol-
vent together with the coupling component in a molar ratio
of 1:2, and treating the suspension with a diazotising agent,
particularly an ester of nitrous acid, such as methyl,
ethyl, butyl, amyl or octyl nitrite, with nitrosylsulphuric
acid or wi-th nitrosyl chloride.
The new colorants are valuable pigments which can
be used in a finely divided form for pigmenting high molec-
ular organic ma-terial, for example cellulose ethers and
cellulose esters, such as ethylcellulose, nitrocellulose,
cellulose acetate or cellulose butyrate, natural resins or
synthetic resins, such as polymerisation resins or condensa-
tion resins, for example aminoplasts, particularly urea-
formaldehyde and melamine-formal~ehyde resins, alkyd resins,
phenoplasts 9 polycarbonates, polyolefines, such as poly-
styrene, polyvinyl chloride, polyethylene, polypropylene 7
polyacrylonitrile or polyacrylic acid esters9 polyamides,
polyurethanes or polyes-tersl rubber, casein, silicone and
. .
silicone resins, individually or as mixtures. -
It is immaterial here whether the high molecular
compounds mentioned are present in -the form of plastic com-
positions or~melts or in the form of spinning solutions,
lacquers or paints. Depending on the end use, it is
found advantageous to use the new pigments as toners or in
the form o~ preparations.
` By vlrtue of their high tinctorial strength and
transparency, the new colorants are particularly suitable
` ~ 0 ~ 5 ~ 2~
for use in printing inks, such as in letterpress, gravure and
offset printing.
CH-PS 522,713 describes a pigment which is obtained
by coupling tetrazotised 1,5-diaminoanthraquinone with 2 mols
-of 3-cyano-4-methyl-2,6-dihydroxypyridine. However,
the colour of -this known pigment is indica-ted as blue, ~Ihile
the pigment obtained in accordance with the invention from
tetrazotised 1,5-diaminoanthraquinone and 2 mols of 3-cyano-
4-methyl-2,6-dihydroxypyridine, the struc-ture of which has
been established by combustion analysis and mass-spectrum,
gives an orange coloration. Compared wi-th the color-
ants described in DAS 1,544,372, the pigments according to
the invention are distinguished by a-particularly high tinc-
torial strength and transparency in printing inks, and also
by better fastness to light and migration.
In the examples which follow, unless otherwise speci-
fied7 the parts denote parts by weight and the percentages -
denote percentages by weight,
Example 1
.
11.9 parts of 1,5-diaminoanthraquinone, in 150 parts ;
~by volume of glacial acetic acid and 30 parts by volùme of
: 1:
concentrated hydrochloric acid, are stirred for several hours !,
~and are then cooled to 0 - 5C and are tetrazotised at this
temperature with 25 parts by volume o~ 4N sodium nitrite solu-
tion. ~he tetrazo solution is made up to a volume of
600 parts wlth ice and water and is clarified by ~il-tration.
18.5 parts of 1-ethyl-2-hydroxy-4-methyl-5-cyano-6-pyridone are
- 12 _
~ , ; ' ' ,.
~ 09~5~1l2~
dissolved in 1,000 parts by volume of dimethylformamide and
100 parts by volume of pyridine and the tetrazo solution is
added dropwise over the course of 1 hour at 20 - 25C, whilst
stirring well. After the addition of the tetrazo solution is
completed, the mixture is stirred for 1 hour at room tempera-
true and is then warmed to the boil. ~ater and acetic
acid are distilled off until the internal temperature reached
is 150C. The mixture is stirred for a further 4 hours at
this temperature, the pigment being converted into a homo-
geneous crystalline form. The mixture is then allowed
to cool to 100C and is filtered and the precipitate is
washed with dimethylformamide, warmed to 100C9 until a vir~
tually colourless filtrate issues. The precipitate is
then washed with cold methanol and finally with water.
After drying in vacuo at 70 - 75C, a soft-grained pigment
which dyes plastics and lacquers in brilliant orange shades,
is obtained. The pigment corresponds to the formula
;
C~3 - ..
~ 2H5
O ~ ~ OHO ~ ~= O HO~y~ ~ o
, 2 S ~ ~=N ~ -N
,
m e table which follows lists further colorants which
are obtained if -the diaminoanthraquinones mentioned in column
I are tetrazotised and coupled, in accordance with instructions
- 13 -
` 1(~4S12~
` .
of Example 1, with the coupling components listed in column
; II. Column III indicates the shade of a 0.2% streng-th
colora-tion achie ed using the colorant in PVC.
. :
,
;, .
'' '
.
., ~ .
: :.
- ~ ,. .
' '':
- ;~
~ ~ -
,, ,
' ` ` :
: ,
4-
,
~ 4 ~ 1 20
~ . . ~
: No. I ~ III
, . ~ . . . ~ _ _ _ _ ~ . ,
2 1,5-diamino- 6-hydroxy-3-cyano-4-methyl-
anthraquino-ne pyrid-2-one orange
3 ll 1-methyl-~3-cyano-4-methyl-6-
. hydroxypyrid-2-one orange
4 n 1-propyl-~3-cyano-4-methyl-6-
hydroxypyrid-2-one orange
" 1-isopropyl~3-cyano-4-methyl-
6-hydroxypyrid-2-one orange
6 1-n-butyl-3-cyano-4-methyl-6-
hydroxypyrid-2-one orange :
7 n 1-benzyl-3 cyano-4-methyl-6-
. hydroxypyrid-2-one bro~n -~
8 ll 6-hydroxy-4-me-thylpyrid-2-one orange
9 . 6-hydroxy-4-methyl-1-ethyl-
pyrid-2-one orange :~
.. 6-hydroxy-4-methyl-1-n-butyl- .
. . . pyrid-2-one orange
11 n 6 hydroxy-L~methyl-3-carbon-
amido-l-me-thylpyrid-2-one orange
12 n 6-hydroxy-4-methyl-3-carbon-
amido-l-ethylpyrid-2-one orange
13 ~ 6-hydroxy-4-methyl-3-carbon-
. . amidopyrid-2-one orange
1~ .1 6-hydroxy-4-methyl-3-carbon- :
: amido~ propylpyrid-2-one orange .. :
n 6-hydroxy-4-methyl-3-carbon- ~ :
amido-l-isopropylpyrid-2-one orange :
:16 " 6-hydroxy-~methyl-3-carbon- : -
amido-l-n-butylpyrid-2-one orange
172,6-diamino- 6-hydroxy-3-cyano-4-methyl-
anthraquinone pyrid-2-one yellow
18 n 6-hydroxy-3-cyano-l-~methyl-1- yellow-
ethylpyrid-2-one orange : .
~ 19 n 6-hydroxy-3-carbonamido-4-
: methyl-l-ethylpyrid~2-one yellow
.
~ ~ ~ 15 : :
5~Z(~
_, _ . _ ~ ~
; No. I II III
___ ,, ,. . _ .-,
20 2,6-diamino- 6-hydroxy-3-carbonamido-4- I .
anthraquinone methyl-l--propylpyrid-2-one yellow
21 ,l 6-hydroxy-3-carbonamido-L~ yello~
methyl-l~isopropylpyrid-2-one orange
22 . " 6-hydroxy-3-carbonamido-4- ...
methyl-l-n-butylpyrid-2-one yellow ,
23 " 6-hydroxy-3-carbonamido-4-
. methyl-l-me-thylpyrid-2-one yellow :-
24 ll 6-hydroxy-3-cyano-4-methyl~l- :
methylpyrid-2-one yellow
" 6-hydroxy-~-cyano-L~methyl-l~ ~.
. propylpyrid-2-one . yellow
26 ll 6-hydroxy-L~methylpyrid-2-one yellow
27 n 6-hydroxy-L~methyl-l-ethyl- ...
pyrid-2-one yellow
28 n 6-hydroxy-4-methyl-1-n-butyl- .. ~
pyrid-2-one yellow ~-
29 2,7-diamino- 6-hydroxy-4-methyl-3 cyano-l- yellow-::~
anthraquinone ethylpyrid-2-one orange
3o ~ 3-cyano-L~carbethox~-1,2- .~:.
(1',2')-benz-(4'~5')-imidaz-
olo-6-hydroxypyrldine bro~n
31 2,6-diamino- 6-hydroxy-3-cyano-4-methyl-1-
7-methyl- ethylpyrid-2~one yellow .
: an-thraquinone .
32 1,5-diamino- 3-cyano-L~phenyl-1,2-(1',2')-
2,6-dimethyl- benz-(4!~5')-imidazolo-6-
anthraquinone hydroxypyridine claret
33 2,6-diamino- 3-cyano-4-methyl-1,2-(1',2')- .
3,7-dibromo- benz-(4',5')-imidazolo-6-
anthraquinone hydroxypyridine red
: ~ 34 l~ 6-hydroxy~4-methylpyrid-2-one yellow
35 2,6-diamino- n : .
1,5-dichloro- .
anthraquinone brown
. .,
~ 16 -
~ ~4~2C)
No I ! II III ¦ .
~ ~
36 2,6-diamino- 3-cyano-4-methyl-1,2-(lt 2')-
1,5-dichloro- benz-(4',5')-imidazolo-6~
anthraquinone hydroxypyridine red
37 2,6-diamino- "
anthraquinone red
38 1,5-diamino- "
anthraauinone red
39 n 3-cyano-4-phenyl-1,2-(1',2l)- ..
benz-(4t,5~)-imidazolo-6- .
hydroxypyridine red ..
40 2,6-diamino- ,- ;
anthraquinone brown ~:
41 . " 3-c~ano-4-carbe-tho -1,`2-
. (1' 27)-benz-(4',5 ~-imid- .
azo~o-6-hydroxypyridine beige
42 1,5-diamino- n : .:
anthraquinone . claret
43 1,5-diamino- CH
anthra~uinone C~ ~ . claret .
¦ ~ OH
C.~3
. : C~3
. l~3 ~:
- ~ ¦ l l C~3~ ¦ lare-t
; -CH3 :-
: . . . ;' ''
': ' ",:
~ ; 7 ~.
~1,0451Z(l
___._ . ~ . . .
No. I II III
. - - . .
1,5-diamino-6-hydroxy-4-methyl-3-acetyl-
an-thraquinone aminopyrid-2-one red
46 2,6-diamino- 6-hydroxy-3~cyano-4-methyl-1- yellow-
xanthone ethylpyrid-2-one orange
47 1,5-diamino- 6-hydroxy-3-cyano-4-methyl-1-
anthraquinone phenylpyrid-2-one orange
48 n 6-hydroxy-3-cyano-4-methyl-1-
(4'-chloro)-phenylpyrid-2-one orange
49 n 6-hydroxy-3-cyano-4-methyl-1-
(4 t -methyl)-phenylpyrid-2-one orange
n 6-hydroxy-3-cyano-4-methyl-1-
(4'-methoxy)-phenylpyrid-2-one orange
,'':
.. ~ ~ ~
65 parts of stabilised polyvinyl chloride, 35 parts
of dioctyl phthalate and 0.2 part of the colorant obtained
in accordance with Example 1 are stirred with one another
and are worked on a twin-roll calender for 7 minutes at
140C. A pure orange_coloured sheet, wi-th very good
fastness to light and migration, is obtained.
Example 52
1,00 g ofthep ~ ent prepared in accordance with
Example 1 is finely ground on an Engelsmann grinding machine
with ~.00 g of lithographic varnish having the composition:
29.4% of linseed oil stand oil (300 poises),
67.2% o~ linseed oil stand oil ( 20 poises),
2.1% of cobalt acetate (870 Co) and
1.3% of lead acetate
and is then printed at 1 g/m on art printing paper in the
- 18 -
~ 5~ZO
letterpress process with -the aid of a blockO A deep
shade of pure and glossy orange, having a very good trans-
parency, is obtained.
The pigment is also suitable for o-ther prin-ting
processes, such as gravure printing, o~fse-t printing and
flexographic printing and gives excellent results in these
` applications too.
10 parts of titanium dioxide and 2 parts of a col-
ouring substance prepared in accordance with Ex~mple 1 are
ground for 48 hours in a ball mill together with 88 parts of -
a mixture of 26.4 parts of coconut alkyd resin,2~0 parts of
melamine-formaldehyde resin (50% solids content), 8.8 parts
of ethylene glycol monomethyl ether-and 28.8 parts of
xylene.
IP this Iacquer is sprayed onto an aluminium foil,
dried at room temperature fcr 30 minutes and then stoved at
120C for 30 minutes, a brilliant orange-coloured lacquering
which has a good gloss and which is disting~ished by very
good stability to overlac~uering, light and weathering, is
obtained. ;;
,, ~
~ ',:
- ,
'
' - ' . '. ' ' - 19 -
. ' "
