CA1156658A - Iminoisoindolinone metal complexes, process for their production and their use - Google Patents

Abstract

Abstract of the Disclosure The invention relates to iminoisoindolinone metal complexes of the formula wherein R is a hydrogen atom, an alkyl group, an aryl radical or a heterocyclic radical, V is a direct bond or a -NH group, X is a hydrogen atom, Y is a halogen atom, Z is an oxygen or a sulfur atom, M is a bivalent metal which may not be an alkaline earth metal, m and n are integers from O
to 4, and the sum of m and n must be 4. These metal complexes colour plastics in strong yellow shades of good fastness to light, migration, atmospheric influences and heat.

Description

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 ~

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 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 - .

, .

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 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 ,., - `~
.. . .
.

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 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 .. .. . _ _ . _ . _ . _ _ ... . ....... . .. . . .. . . .. . .. . " . . . .. .. . .. .. ...... ....... . ..... . . . .

~, _ 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 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 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 . ~ ' !
~, ', , 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 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 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~

:, : .: - : - , , -,, -"

(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 ~

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.

,, . . .... ~ .

:

,

Claims (9)

What is claimed is:

1. An iminoisoindolinone metal complex of the formula wherein R is a hydrogen atom, an alkyl group, an aryl radical or a thienyl, furyl or pyridyl radical, V is a direct bond or a -NH group, X is a hydrogen atom, Y is a halogen atom, Z is an oxygen or a sulfur atom or a -NH
group, M is nickel cobalt or copper, m and n are 0 to 4, and the sum of m and n must be 4.

2. A metal complex according to claim 1 of the formula wherein R1 is a C1-C4alkyl group, a phenyl group which is unsubstituted or substituted by halogen atoms, methyl groups, C1-C4alkoxy groups or by a further phenyl group, or is a naphthyl radical, cobalt or copper.

3. A metal complex according to claim 3, wherein R1 is an alkyl group of 1 to 3 carbon atoms.

4. A metal complex according to claim 3, wherein R1 is the benzoyl or p-chloxobenzyl radical.

5, A metal complex according to claim 3, wherein M is cobalt.

6. The compound according to claim 1 of the formula

7. The compound according to claim 1 of the formula

8. The compound according to claim 1 of the formula

9. The compound according to claim 1 of the formula l0. An organic material of high molecular weight selected from cellulose ethers and esters, natural resins and synthetic resins, alkyd resins, phenolic plastics, polycarbonates, polyolefins, polystyrene, polyvinyl chloride, poly-acrylonitrile, polyacrylates, polyamides, polyurethanes and polyesters, rubber, casein, silicon and silicone resins, singly or in mixtures, containing a metal complex according to claim 1.