Note : Les descriptions sont présentées dans la langue officielle dans laquelle elles ont été soumises.
-- 1 --
Case 3-.l246
Canada
Iminoi.soil~clolinonc metal complexes, process :Eor th~ir
production and their use
The present invention relates to iminoisoindolinone metal
complexes of the formula
y
n~- ~ m
l! I N
~ M/ li t- NFICOVR (I)
RVCONHt~ ~ o
X Y
m n
wherein R is a hydrogen atom, an alkyl group an aryl radiaal
ora thienyl, furyl or pyridyl radical, V is a dire¢t bond or
a -NH group, X is a hydrogen atom, Y i5 a halogen atom, Z i5
an oxygen or a sulfur atom o~ a -NH group, M is nick~l,
copalt or coppex, m and n are O to 4, and thç ~Um o~ m and
n must be 4.
An alkyl. group R i5 pre~er~bly a Cl-C6alkyl gro~p~ ~h~ alkyl
groups can be both straight-chain and branche.d, and they
can be substituted by halogen atoms, e.g. chlorine at~ms~
or by alkoxy groups of 1 to 4 carbon atoms or by phenyl
groups. R is preferably a 2-furyl, 2-thienyl or 3-pyridyl
radical. V is preferably a direct bond, Y is
: . . , , ,, -
.
; ~.
.. . :: ,
5 ~
pre~:erably a chlorine atom and Z is advantageously the -NH
group.
Particularly interesting metal complexes are those of the
formula
~ ~ NH
~ b/) , :
wherein Rl is a Cl-C4alkyl group, a phenyl group which is
unsubstituted or substituted by halogen atoms, methyl
groups, Cl-C4alkoxy groups or by a further phenyl gro~lp,
or is a naphthyl radical, and M is nickel, cobal~ or
copper.
The metal complexes of the invention are obtained by
trea~ing an iminoisoindolinone of the ~ormula
/Z\.~ \.
N~ NHCOVR
, . N
i ~ H (III)
o
:
5 ~
- 3 -
wherein R, V, X, Y, Z and m have the given meanings, with
a~ents which donate nickel, copper or especially, c~bal-t.
Particularly interesting starting materials axe those
iminoisoindolinones of the formula III in which Z is the
-NH group, m is 4 and n is O.
The imlnoisoindolinones of the formula III are obtained by
known methods by condensing an isoindolinone of the formula
. ~ ~./ \
~ (IV)
wherein X, Y, m and n have the glven meanings and U is a
group of the formula
Y~ /Y X
/.\ or '!
wherein X is an imino or a thiol group and Y is a halogen
atom, a Cl-C4alkoxy group or a secondary amino group, wlth
an amine of the formula
RVCONH ~ NH~ ~V~
. .
~ 8
-- 4 --
wherein R, V and Z have the given meanings.
The amines of the formula V are obtained by monoacylation
of 2-nitro-1,4-phenylenediamine with the corresponding
carboxylic acid chloride to give l-amino-2-nitro-4-
acylaminobenzene, catalytic hydrogenation of this latter
to give 1,2-diamino-4-acylaminobenzene, and reaction o~
this compound with bromocyanogen.
Examples of isoindolinones of the formula IV are:
5,6-dichloro-3-iminoisoindolinone, 4,5,6,7-tetrachloro-3-
iminoisoindolinone, 3,3-dimethoxy-5-chloroisoindolinone,-
3,3-dime~hoxy-6-iodoisoindolinone, 3,3-dimethoxy-7-chloro-
isoindolinone, 3,3-dimethoxy-7-fluoroisoindolinone,
3,3-dimethoxy-4,5-dichloroisoindolinone, 3,3-dimethoxy-
4,6-dichloroisoindolinone, 3,3-dimethoxy-4,5,6,7-tetra-
chloroisoindolinone and especially 3-iminoisoindolinone.
The above isoindolinones are known compounds.
Examples of amines of the formula V are:
2-amino-5- or -6-acetylamino-benzoxazole, 2-amino-5- or
-6-propionylamino-benzoxazole, 2-amino-5- or -6-benzoylamino-
benzoxazole, 2-amino-5- or -6-acetylamino-benzthiazole,
2-amino-5- or -6-propionylamino-benzthiazole, 2-amino-5 or
-6-benzoylamino-benzthiazole, 2~amino-5- or -6-form~lamino-
benzimidazole, 2-amino-5- or -6-acetylamino~benzimidazole,
2-amino-5- or -6-propionylamino-benzimidazole, 2-amino-5- or
-6-butyryl~mno-benzimidazole, 2-amino-5- or -6-chloroacetyl-
amino-benzimidazole, 2-amino-6-methoxyacetylamino-benzimida-
zole, 2-amino-5-phenacetylamino-benzimidazole, 2-amino-5-
benzoylamino-benzimidazole~ 2-amino-5-o-, m- or p-chloro-
benzoylamino-benzimidazole, 2-amino-5-(2'~5'-dichloro-
benzoylamino)-benzimidazole, ~-amino-5-(2',4'-dichloro
benzoylamino)-benzimidazole, 2-amino-5-o-, m- or
- .
,
.
-- 5 --
p-methoxybenzoylamino-benzimidazole, 2-~mino-5-p-
diphenylylcarbonylamino-benzimidazole, 2-amino-5-~-
~thoylamino-benzimidazole, 2-amino-5- or -6-2'-furoyl-
amino-benzimidazole~ 2-amino-5- or -6-2'-thienoylamino-
benzimidazole~ 2-amino-5- or -6-3'-pyridincarbonylamino-
benzimidazole.
The amines of the formula III can also be obtained by
condensing a nitroamine of the formula
~.~-\.
2 ~ ~ ~. 2
with an isoindolinone of the formula IV, reducing the nitro
compound thereby obtained to the amine of the ormula
.~\.
. ~ (VII)
~-\.f
Y~ O
and treating this latter with agents which dona~e the acyl
radical -COVR. This process is particularly advantageous
if VR is a Cl-C6alkyl radical.
The condensation of the isoindolinones with the amines of
the formula V takes place partly even at low temperature,
if necessary by warming the intimately mixed components and
especi~y advan~ageously in the presence of an inert organic
solvent, i.e. one that does not participate in the
reaction.
. ~ .
'' ,,
~ 5
-- 6 --
Where 3-imino-~ 3-thio- or 3,3-bis-tert-amino-
isoindolin-l-ones or alkali salts of 3,3-dialkoxy-
isoindolin-l-ones are used as starting
materials, then it is advantageous to use water-miscible
organic solvents, e.g. lower aliphatic alcohols such as
alkanols, for example methanol, isopropa~Dl or butanol,
or lower cyclic et~ers such as dioxane or ethylene glycol
monomethyl ether. In doing so, the condensation is able to
take place even at relatively low temperatures. It is
advantageous to conduct the reaction in the presence o~ an
agent binding alkali and organic bases, for example a lower
fatty acid which can be used simultaneouly as solvent,
especially acetic acid.
As the resultant condensation pr~ducts are reluctantly
soluble in the specified solvents, they can be readily
isolated by filtration. Any impurities can be removed by
washing off.
For conversion into the metal complexes, the isoindolinones
obtained are treated with agents which do not donate
alkaline earth metals, e.g. zinc or cadmium donors, but
especially nickel, copper and cobalt donors. It is preferred
to employ the forma~es, aceta~es or stearates of these
metals, e.g. nickel(II) acetate, copper(II) acetate,
cobalt(II) acetate or cobalt(II) acetylacetonate. The
metallising is conducted advantageously in one of the
solvents specified above~ or in a mixture thereof, or
especially in dimethyl formamide, ethylene glycol mono-
alkyl ether or diethylene glycolmonoalkyl ether.
It is also possible to carry out condensation and metallising
continuously in the same reaction vessel. Instead o~ using
individual salts it is also possible to use mixtures of
such metals, in which case mixed metallised complexes
,., - `~
.. . .
.
- 7 -
are obtained,
The imidazole derivatives are especially interesting
because of their favourable combination of excellent fastness
t~migration9 light and atmospheric influences.
The novel compounds are useful pigments which, in finely
dispersed form, can be used for pigmenting organic material
of high molecular weight, for example cellulose ethers
and esters, such as ethyl cellulose, nitrocellulose,
cellulose acetate, cellulose butyrate, natural resins or
synthetic resins such as polymerisation or condensation
resins, for example aminoplasts, in particular urea/formal-
dehyde and melamine/formaldehyde resins, alkyd resins,
phenolic plastics, polycarbonates, polyolefins such as
polyethylene, polypropylene or polyisobutylene, and also
polystyrene, polyvinyl chloride, polyacrylonitrile,
polyacrylates, polyamides, polyurethanes or polyesters,
rubber, casein, silicon and silicone resins, singly or in
mixtures.
The high molecular weight compounds specified a~ove can
be in the ~n~ of plastics, melts or of spinning solutions,
lacquers, paints or printing inks. Depending on the end use,
it is advantageous to use the new pigments as toners or in
the form of compositions.
The strong yellow coLourations obtalned are distinguished
by good fastness to light, migration, atmospheric
influences and heat.
Compared with the metal complxes described in British patent
specification l 512 554, the compounds of the present
invention are distinguished by substantially greater eolour
strength and also by the fact that they are obt~ined in a
., .
-
- 8 _
fonm which makes conditioning unnecessary.
The invention is illustrated by the fo~bwing Examples, in
which percenta~es are by weight.
`
5 ~3
9 _
Example 1; A s~irred mixture of 12 . S g of 2-amino-5-
benzoylamino-benzimidazole and 9.1 g of phthalimidine
hydrochloride is kept at re1ux for 3 hours in 120 g of
ethylene glycol monoethyl ether. The precipitated product is
then collected by filtration at room temperature, washed
with methanol and water, and then dried in vacuo at 90-100C.
The product is a yellow crystall ine powder of the formula
. .
With s~irring, a mixture of 5 g of this product and 1.8 g
of nickel acetate tetrahydrate is heated in 100 g of
diethylene glyco~monoethyl ether for 15 hours at 145-150C.
The pigment is collected by filtration at 100C and washed
with cold m~hanol, acetone and water, and then dried. It
is a yellow crystalline powder which can be dispersed e.g.
by grinding in isopropanol with the aid of grinding
elem`ents. When incorporated in polyvinyl chloride
sheeting or used for pigmenting lacquers, it affords yellow
colourations of excellent colour strength, and good ~astness
to light and atmospheric influences.
Table 1 lists pigments which can be obtained
by the method described in Example L under ~he same reaction
conditions. They are pigments of the general formula II.
The respective meaning of Rl is given in column 2, that
of the metal atom M in column 3, and the shade of the
pigmen~ed lacquers is indicated in column 4.
`
1 1 a~58
- 10 -
Table I
~ ~ n . Shade of the
No. . . :Metal atom lac~uer
2 phenyl Ca reddish yellow
3 methyl Ni reddish yellow
4 methyl co reddish yellow
; 2,5-dichlorop~enyl co yellow
6 2,5-dichlorophenyl cu greenish yellow
7 2,4-dichlorophenyl Co reddish yellow
8 2,4-dichlorophenyl Ni yellow
9 2,4-dichlorophenyl Cu greenish yellow
lo 3,4-dichlorophenyl N. yellow
11 3,4-dichlorophenyl Co ~ reddish yellow
12 ~-naphthyl Co yellow
13 4-diphenylyl Ni yellow
14 4-diphenylyl Co reddish yellow
15 2,6-dichlorophenyl Co yeLlow
16 4-chlorophenyl co reddish yellow
17 4-chlorophenyl Ni yellow
18 4-chlorophenyl cu greenish yellow
19 2-methylphenyl ~i ~reenish yellow
20 2-methylphenyl Co yellow
21 3-methylphenyl Ni yellow
22 3-methylphenyl co reddish yellow
23 4-methylphenyl co reddish yellow
24 4-methylphenyl Ni yellow
. . . ,, _ . . . ._ _.
Example 25: 47 g o the nitro compound of the formula
~. ~o
.
5 8
(obtained by condensation of 2-amino-3-nitrobenzimidazole
with iminophthalimide hydrochloride), are hydrogenated in
500 ml of dimethyl formamide with 15 g of Raney nickel at
70-75C. The uptake of hydrogen is 10.1 litres
(99 % of theory). The catalyst is removed by filtration and
the corresponding amine is precipitated in the form of
orange crystals by slowly stirring 2000 ml of water into the
clear solution.
With stirring, 10 g of this amine are heated in 100 ml o~
o-dichlorobenzene to 110 C, then 4.05 g of acetic anhydride
are added dropwise and stirring is continued for 1 hour at
115-120C. After cooling to room temp~rature, the re~ction
mixture is filtered and the filter cake is washed with
methanol and water~ The product is metallised with nickel
acetate tetrahydrate as in Example 1. The resultant pigment
is identical with that obtained in Example 3.
The above nitro compound can also be obtained as follows:
12.1 g of phthalodinitrile are stirred in 120 ml of
isopropanol, 60 ml o o-dichlorobenzene and 9.9 g of
50 % sodium hydroxide for 2 hours at 30-35C.Then 3.1 ml
of 96 % sul~uric acid are added and stirring is continued
or 30 minutes. Then water and isopropanol are distilled
off in vacuo while slowly heating to a maximum temperature
of 65 C. Then 16.1 g of 2-amino-5-nitrobenzimidazole are
added and thebatdh is heated to 130-135C and stirred
for 2 hours at this temperature. After cooling, the
reaction mixture is filtered and the filter cake is washed
with methanol and hot water, affording 19.1 g of yellow
crystalline nitro compound which can be ~rystallised e.g.
from dimethyl formamide.
- 12 _
Example 26: The prcedure of Example 25 is repeated~ but using
cobalt acetate tetrahydrate as metal donor. The pigment
obtained is identical with that o~ Example 4.
Example 27: The procedure of Example 25 is repeated, but
using an equivalent amount o~ propionic anhydride instead of
acetic anhydride. Pigmen~s which are very similar to those
of Example 25 are obtained after metallising.
Example 28: With stirring, 23.2 g of the amine obtained
i~ accordance with Example 25, paragraph 1, are heated in
250 ml of o-dichlorobenzene and 6.75 ml of pyridine to 110C.
Then 16.2 g of 4-chlorobenzoyl chloride are slowly added
dropwise and the temperature is kept at 115-120C for l
hour. After cooling to room temperature the reaction mix~ure
is filtered and the precipitate is washed thoroughly with
methanol and water, and then dried in vacuo at c. 100C.
metallis~ with cobalt, nickel or coipper acetate yields
pigments which are identical of those of Examples 16, 17
and 18 respectively.
Examples 29-33: The proa~ure of Example 28 is repeated,
replacing 4-chlorobenzoyl chloride by equivalent amounts of
the acid chlorides listed in Table 2. Similar pigments are
obtained.
Table II
~ __ .... ~
No. Acid chloride Metal Shade
_ _ _ _ _ , ~, _
29 diphenyl-4-carboxylic co reddish yellow
acid chloride (identical wi~h Ex
isobutyryl chloride Ni yellow
31 isobutyryl chloride co reddish yellow
32 isobutyryl chloride Cu greenish yellow
33 chloroacetyl chloride Co reddl~1 ~ellow
.. .. . _ _ . _ . _ . _ _ ... . ....... . .. . . .. . . .. . .. . " . . . .. .. . .. .. ...... ....... . ..... . . . .
~,
5 8
- L3 -
_
No. Acid chloride Metal Shade
_ _ _ .
34 4-methoxybenzoyl chloride Ni yellow
35 4-methoxybenzyol chloride co reddish yellow
36 thiophene-2- carboxyl ic Ni yellow
acid chloride
31 thiophene~2- carboxyl ic Co reddish yellow-
acid chloride
38 furane-2-carboxylic acid Ni yeLlow
chloride
39 furane-2-carboxylic acid Co reddish yellow
chloride
40 pyridine-3-carboxylic acid ~i yellow
chloride
41 pyridine-3-carboxylic acid Co reddish yellow
chloride
. _,
Example 42: 15.75 g of methyl 3,4,5,6-tetrachloro-o-
cyanobenzoate are added to a solution of 100 ml of
methanol and 2.7 g of sodium methylate and the mixture is
stirred for l/2hour. Then L2.8 g o-E 2-amino-5-benzoyLamino-
benzimidazole are added and stirring is continued for
15 hours. The mixture is diluted with 100 ml of o-dichloro-
benzenP and acidified with 5 ml of acetic acid, whereupon
the free orange pigment precipitates. With stirring, the
temperature is raised to 150C while distilling off
methanol. The batch is co~led after 2 hours and the
precipitate is collected by filtratio~, washed with
o-dichlorobenzene, methanol and water and dried. affording
the pigment of the formula
-C~+ 1--W ~ '~
0 O . ~ /C
Cl/ ~ ~ \Cl
1 1 ~B~58
- 14 -
A mix~ure of 5.19 g of the above tetrachloroisoindolinone
pigment and 1.1 g of copper acetate tetrahydrate is hea~ed
in diethyLene glycol monoethyl ether ~or 15 hours to
14 gl50 C. The precipitated copper complex is isolated by
filtration at 100C, washed with cold methanol, acetone and
water and dried, affording 5.1 g of a pigment powder.
Lacquers pigmented with this copper complex produce yellow
finishes of good fastness to atmo~he~ influences.
Examples 43-50: Table 3 lists pigments which are obtained
by the method described in ~xample 42 under the same
reaction conditions. These pigments contain the aroylamino
groups listed in column II and the metals listed in
column III.
Table 3
~o A~oylamLno group I M Shade
_ .~ . ,
43 benzoylamins Ni yelLow
44 benzoylamino Co reddish yellow
45 p-chloroben~oylamino Cu reddish yellow
46 p-chlo~obenzoylamino Co red~ish yellow
47 p-chlorobenzoylamino ~i yellow.
48 diphenyl-4-carbonylamino Cu reddish yellow
49 diphenyl-4-carbonylam~o ~i reddish yellow
diph~nyl-4-carbonylamLno C~ yellow
~ l ~B~58
- 15 -
Example 51: Table 4 lists pigments which were obtained by
the method described in Example 42 under the same
reaction conditions. Column II indicates the respective
methyl 2-cyanobenzoate used instead of methyl 3,4,5,6-
tetrachloro-2-cyanobenzoate. The aroylamino groups of
the 2-aminobenzimidazole radical are indicated in column III
and the metals in column IV. Column V indicates the shades
of the pigmented lacquers.
Table 4
No~ MethyL 2-cyanobenzoate rou Metal Shade
~ P
51 3,4,5,6-tetrabromo- 4-chloro- Ni reddish
~. benzoylamino ~ellow
52 3,4,5,6-tetrabromo- 4-chloro- co ..
benzoylamino
53 3,4,6-trichloro-5- 4-chloro- Ni
methoxy- benzoylamino~;
54 3,4,6-trichloro-5- 4-chloro-- co
methoxy- benzoylamino
3,:4~6-trichloro-5-~4'- 4-chloro~ Ni ,.
chlorophenoxy)- benzoylamino
56 3,4,6-trlchloro-5-~4'- 4-chloro- co
c~lorophenoxy)- benzoylamino
57 4,5-dichloro- dlphenyl-4- ~i yellow
. carbonylamino .
58 4,5-dichloro- diphenyl-4- Co
_ _ carbonylamino
. ~ ' !
~, ', ,
5 8
- 16 -
Example 59: With stirring, a mixture of 6.38 g of the
pigment o the formula
~ \ H ~0
C~3-co-NH-~
o\
\.~
1 095 g of zinc acetate dihydrate and 1.245 g of cobalt
acetate tetrahydrate, is heated in 100 ml of diethylene
glycol monoethyl ether for 15 hours to 145-150C. The
reaction mixture is cooled to 100C and filtered. The
filter cake is washed with methanol, acetone and water,
then dried in vacuo at 100C, affording a pigment which~
when incorporated in PVC or lacquers, gives a substantially
greener shade than the pure cobalt complex, yet still has
good fastness properties. (The pigment contains 4.04 % of
cobalt and 4.54 % o zinc; calculated: 4.22 % of cobalt and
4.68 % of zinc).
Example 60: 13.85 g of the amine obtained according to
Example 25, paragraph 1, are heated in 150 ml of o-dichloro-
benzene. Then 6.13 g of phenylisocyana~e are added drop~
wise and, with stirring, the teMperature is kept for 3
hours at 145-150C~ The reaction mixture is cooled to
room temperature and filtered. The filter cake is washed
with a small amount of mPthanol and hot water and then dried,
affording 15 ~ of a product of the formula
N~ CO N~ 11 11 1 i
~0/
. . . -, .
- . . ~
., .
~ 8
- 17 -
With stirring, a mixture of 4 g of this product and 1.38 g
of cobalt acetate tetrahydrate is heated in 100 ml of
diethylene glycol monoethyl ether to 145-150C Eor 15
hours. The reaction mixture is filtered at 60 C and the
filter cake is washed with methanol, acetone and water~ to
give a brown powder which, when finely dispersed and
incorporated in polyvinyl chloride sheeting, gives a brown
colouration.
Example 61: The procedure of Example 60 is repeated,
replacing phenylisocyanate by 3,4-dichlorophenylisocyanate,
to give the corresponding 3,4-dichlorophenylurea derivative.
The nickel complex of this pigment, prepared by the proeess
of Example 60, paragraph 2, gives yellowish-brown
colourations in polyvinyl chloride or in lacquers.
Example 62: The procedure of Example 61 is repeated to
produce the cobalt complex, which likewise gives yellowish-
brown colourations in PVC or lacquers.
Example 63: 58.3 g of the nitro compound of the ~ormula
N N--.~
1 1! 1! ! !
02N ~ t~ i~
(obtained by condensation of 6-nitro-2 aminobenzthiazole
with iminophthalimino hydrochloride) are hydrogenated in
600 ml of dimethyl ~ormamide at 20 -25 C with 12 g of
palladium on carbon. The uptake of hydrogen is 11.91 li~res
(99 % of theory). Then 1000 ml o dimethyl formamide are
added and the precipitated amine is dissolved a~ 100C and
the catalyst is removed by iltration. The amine is precipi-
tated by the slow addition of 3000 ml of water, collected
by filtration, washed with methanol and water, and then
. ~ ,
1 15~B58
- 18 -
dried. The amine ~ reacted by the process described in
Example 25, paragraph 2,or Example 28, with the respective
acylating agent indicated in column II of Table 5 and with
the metal indicated in column III. Column IV indicates
the shade of the pigmented lacquers.
Table 5
. .
No. Acylating agent Metal Shade .
64 acetic-anhydride Co redd~ yellow
ll Ni ., . "
66 ,l Cu yeLlow
67 benzoyl chL~ride Co reddish y~llow
68 ,. Ni ! -
69 .l Cu yellow
70p-phenylbenzoyl chloride co reddish yellow
71I. Ni I.
72I. Cu yellow
73p-chlorobenzoyL ~hloride Co yeLlowish-brown
74I~ Ni .
75 I~ Cu ll _. _
Example 76: g3 g of the nitro compound o the ~ormula
2.~ N ~~
\o/ ~ \g~
:, : .: - : - , , -,, -
"
- 19 -
(obtained by condensation of 5-nitro-2-aminobenzoxazole
with iminophthalimide hydrochloride) are hydrogenated in
1800 ml of dimethyl fcrmamide at room temperature with
18 g of Raney nickel. The uptake of hydrogen is 20.6 litres
~102 % of theory). The suspension is diluted with 1000 ml
of dimethyl formamide, heated to 100C, and a solution is
obtained. The calayst is removed and then the amine is
precipitated by the addition of about 2000 ml of water,
collected by filtration, washed with methanol and water, and
dried in vacuo at 70 C. This amine is then reacted by the
process of Example 25, paragraph 2,or Example 28, with the
respective acylating agent listed in column II o~ Table 6,
and then metallised by the process of Example 1 with the
respective metal of column III Column IV indicates the
shades of the lacquers pigmented with the pigments so ob-
tained.
Table 6
. No. Acylating agent - Metal Shade .
. ,
76 acetic anhydride_-- Ni greenish yellow
77 ,. co reddish yellow
78 benzoyl chloxide Co yellow
79 .7 Ni greenish yell~w
80p-chlorobenzoyl chloride Co yellow
81,l ~i greenish yellow
82p-phenylbenzoyl~ chloride co reddish yellow
83. Ni greenish yellow
84 f~rmic acid co yellow
G 5 ~
- 20 -
Example 85: 65 parts of stabilised polyvinyl chloride~
35 parts of dioctyl phthalate and 0.2 part of the pigment
obtained in Example 1 are stirred together and then rolled
for 7 minutes at 160C on a two-roll calender to produce a
brilliant yellow sheet of very good fastness to light and
migration.
Example 86: 10 g of titanium dioxide and 2 g of the pigment
obtained in Example 1 are ground for 48 hours in a ball mill
with 88 g of a mixture of 26.4 g of coconut alkyd resin,
24 g of melamine/formaldehyde resin r50 % solids content),
8.8 g of ethylene glycol monomethyl ether and 28.8 g of
xylene.The resultant lacquer is sprayed onto an aluminium ~:~
sheet, predried for 30 minutes at room temperature, and
then stoved for 30 minutes at 120 C. The brilliant yellow
finish obtained has very good fastness to overstripe
bleeding, light and atmosphericinfluences 9 and has good
colour strength.
Exam~le 8 ?
A polypropylene te~ephthalate granulate suitable for
f;bre manufacture is shaken in a closed vessel for 15
minutes on a mechanical shaker together with 1 % of the
pigment of Examplel~The uniformly coloured granules are then
spu~ in a melt spinning machine to filaments, which are
stretched and wound on a draw twister. Yellow fibres with
excellent properties are obtained.
,, . . .... ~ .
:
,
