DE2523175A1 - ORGANIC COMPOUNDS - Google Patents

Description

SANDOZ-PATENT-GMBH

r, ν. Case 150-3621 L ö rrach

Organic compounds

The invention relates to pigment dyes Formula I.

wherein R _{1 is} alkyl,

R alkylcarbonyl, alkoxycarbonyl or a Group of the formula -CONR.-R. ,,

D /

R hydrogen or alkyl,

Usually one bound in the ortho or peri position carbo- or heterocyclic radical of aromatic character,

50985 1/097 0

Case 150-3621

Rc which is used to complete a carbo-

or heterocyclic ring of aromatic character, R ,. Hydrogen or alkyl, R_ hydrogen, alkyl or a single or

binuclear carbo- or heterocyclic radical of aromatic character and Me is a divalent transition metal atom or

zinc

mean, whereby all mentioned residues of aromatic character are those in the chemistry of pigment dyes usual substituents, including a carboxyl group in the molecule, and can carry fused rings. The dyes of the formula I a are of particular interest

R,

(Ia),

where R,

Hydrogen or methyl,

C -alkyl or C -alkoxy or a l— ζ ι— δ

Group of the formula -NH R,

1,2-phenylene that has up to two substituents can carry 1,2-, 2,3- or 1,8-naphthylene, 9,10-phenanthrylene, 5,6-acenaphthylene or a residue of the formula

509851/0970

Case 150-3621

12th

or

one optionally up to two substituents

supporting radical of the formula -CH = CH-CH = CH- *

or -CH = CH-

or a residue of the formula

-NH-CO-C = C-, -C = N

Ii i

CN R ₁ . OH 14

or

13th

^R 14 ^R 15 Me,

-N-N = C-,

I I

where the marked with *

14th

Atom is bonded to the carbon atom, which in turn is bonded to oxygen, hydrogen, C _1-4 -AIlCyI, naphthyl, benzimidazolonyl-5 or phenyl, which optionally carries up to three substituents, including up to three methyl, up to two from the Group chlorine, bromine, nitro and C 1, -alkoxy and / or one from the group Cp-alkylcarbonylamino, optionally further substituted benzoylamino and optionally further substituted phenylaminocarbonyl, methyl or phenyl,

Mean hydrogen, methyl or phenyl and nickel, copper, zinc or cobalt and the aromatic nuclei, where indicated, can carry one or two substituents, including up to two from the group chlorine, bromine, methyl, C. - alkoxy and nitro and / or one from the group consisting of cyano, hydroxy, alkoxycarbonyl, aminocarbonyl, ■

509851/0970

- 4 - Case 150-3621

C, - alkylaminocarbonyl, di-C, "-alky1-aminocarbonyl, Carboxyl, phenyl and phenoxy.

Preferred among the new dyes are those of the formula Ib

H / \ H

(Ib),

wherein A is methyl, C -alkoxy, amino, C "-alkylamino or benzimidazolonyl-5-amino or optionally up to three substituents, including up to three methyl, up to two from the group consisting of chlorine, bromine, nitro and C 1 -alkoxy and / or one from the group C, -Alkylcarbonylamino, Phenylcarbonylamino and phenylaminocarbonyl bearing phenylamino, where the first two phenyl nuclei have up to two substituents from the group chlorine,

Can carry bromine and C _{1 -alkoxy,}
1 ~ t.

B 1,2-phenylene, which has up to two substituents including up to two from the group consisting of chlorine, bromine, methyl and C -alkoxy and / or one Cyano, hydroxy, nitro, C 1, -alkoxycarbonyl, aminocarbonyl or carboxyl group can carry, 2,3-dihydroxyquinoxalinylene-6,7 or benzimidazolonylene-5,6,

D is a radical of the formula -CH = CH-CH = CH-, the

one or two substituents, including up to two chlorine, bromine or methoxy and / or can carry a nitro or a remainder of the

509851/0970

- 5 - Case 150-3621

formula —Γ * - M.
OH ' or —C ^{s =}
I.
CH ₃ c -
I.
CN co b NH -, -N -N -C- -C = CH- ΓοΤ V ₅ CH a

a hydrogen or a carboxyl group, b hydrogen, chlorine, bromine or nitro and Me_ nickel or copper

mean.

The pigments of the formula Ic are particularly preferred

wherein A- benzimidazolonyl-5-amino or optionally up to three substituents, including up to three methyl, up to two selected from the group chlorine, bromine, nitro and C alkoxy and / or from the group of C, ₂ ~ alkylcarbonylamino, Phenylcarbonylamxno and Phenylaminocarbony1 bearing phenylamino, where the first two phenyl nuclei can carry up to two substituents from the group consisting of chlorine, bromine and C _1-3 -AIkOXy, B-ortho-phenylene, the one substituent

from the group of chlorine, bromine, methyl, methoxy and nitro can carry, or benzimidazolonylene-5,6,
D _{1 is} a radical of the formula -CH = CH-CH = CH-,

509851/0970

- 6 - Case 150-3621

■?

-C = C - CO - NH '^ _n ■ or

? T [Q} ^or " ^{CH =}

COOH "^

and Me_ mean nickel or copper. The pigments of the formula Id are particularly preferred

(Id),

wherein A ^ is phenylamino which optionally has a substituent carries from the group chlorine and methyl and / or two methoxy groups in the 2,5-position, B-ortho-phenylene, which consists of a substituent the group can carry chlorine, methyl or methoxy, or benzimidazolonylene-5,6,

D _{n is} a radical of the formula -C = CH 2 ι

COOH

-C = N -Tr ^ or -C = C - CO - NH I ) &

OH ^ ^CH 3 ^CN

and Me mean nickel.

Regardless of the other substituents, R- in formula Ia preferably corresponds to one of the meanings of A, especially A and especially A.

R corresponds to, regardless of the meaning of the rest Substituents on the molecule of the formula Ia, preferably

SO 98 5 1/0970

- 7 - Case 150-3621

one of the meanings of B, especially B and especially B.

In preferred cases, R in formula Ia corresponds to one the meanings of D, especially D and especially D> Me, in formula Ia is independent of the meaning of Substituents, preferably copper and especially nickel.

The process for the preparation of the new compounds of the formula I is characterized in that one Compound of formula II

or one of its tautomeric forms, with a salt, preferably a water-soluble salt, e.g. the chloride, Sulfate, nitrate or formate, especially the acetate, of a divalent transition metal atom or of zinc metallized.

The metallization takes place in a generally known manner; since the compounds of formula II mostly in e.g. water, Alcohol, ketones or hydrocarbons are sparingly soluble, they are e.g. in N, N-dimethylformamide dissolved or suspended in a solvent, metallize.

The compounds of the formula II are new and some of them also have pigmentary character, which is why they are also

50985 1/0970

- 8 - Case 150-3621

if subject of the present invention. Their production or in the presence of a metallizing Compound simultaneous preparation of the compounds of the formula I is carried out by one mole of one Diamines of formula III

H ₂ N - R ₄ - NH ₂ (III)

with one mole of an ortho-hydroxyaldehyde of the formula IV

O = CH. -.

Hr ^(iv)

and with one mole of a compound of formula V

(V)

where R _{0 is} alkyl or hydrogen,

condensed, the condensation being carried out in the presence or absence of a salt of a divalent transition metal or of zinc. The condensation generally takes place in an inert solvent, for example water, one to four carbon atoms containing alcohol, glycol or Glykolather or in dimethylformamide, at temperatures between about 20 ° and 150 ⁰ C, preferably 40 ° to 100 ⁰ C instead. The reaction products can easily be isolated from these solvents by filtration. In the case of dimethylformamide, it may be necessary to add water, for example, to the hot solution until it becomes slightly cloudy and then to cool and filter.

509851/0970

- 9 - Case 150-3621

The compounds of the formulas III, IV and V are known or can be prepared analogously to known production processes easy to manufacture.

The reaction product of one mole of a diamine of the formula III with the ortho-hydroxyaldehyde of the formula IV can, but does not have to be, isolated in the reaction sequence described above.

Compounds of the formulas I or II can also be prepared by condensation of one mole of a compound of the formula IV with one mole of a compound of formula VI

\ NH NH

R ₂ _ / ^z (VI)

optionally in the presence of a

Salt of a divalent transition metal atom or of zinc.

This condensation is also generally carried out under the abovementioned conditions.

The compounds of the formula VI are likewise new and are therefore the subject of the present invention. They are produced by condensation of one mole of a compound of the formula III with one mole a compound of the formula VII

- ^R 8

₂ - \

Where

S0386 1/0970

- 10 - Case 150-3621

This condensation also generally takes place under the abovementioned conditions.

The new pigments of the formula I are excellently suited for coloring plastic masses, including solvent-free ones and solvent-based materials made of plastics or synthetic resins (in paints on an oily or watery basis, in varnishes of various types, for spin dyeing of viscose or Cellulose acetate, for pigmenting polyethylene, polystyrene, polyvinyl chloride, rubber and synthetic leather). You can also use printing inks for the graphic industry, for pulp coloring, for coating of textiles, or for pigment printing.

The dyeings obtained are characterized by their fastness to heat, light and weather, their migration and Solvent fastness, its color strength and the very good application properties, e.g. fastness to flocculation, Fastness to crystallization, fastness to dispersion and opacity.

By post-treating the raw pigments in organic solvents at elevated temperatures, e.g. 110 ° -200 ° C the pigment properties can often be further improved. As organic solvents (in which the Pigments themselves but cannot be dissolved) are e.g. chlorobenzene (mixture), nitrobenzene, dimethylformamide, Glacial acetic acid, ethylene glycol or quinoline can be considered.

In the following examples, parts are parts by weight and percentages are percentages by weight. The temperatures are given in degrees Celsius.

5 0 9 8 5 1/0470

- 11 - Case 150-3621

example 1

24.6 parts of 5,6-diaminobenzimidazolone are used in 190 Part suspended in boiling methanol. 35 parts are added to this mixture with stirring α-ethoxymethylene acetoacetanilide, dissolved in 240 parts of warm methanol / slowly added. The suspension is refluxed for 6 hours, cooled, the residue is filtered off and washed with ethanol. After drying in vacuo at 70 °, the yellow product of the formula

6 5

obtained with good yield.

17.6 parts of the above product are dissolved in 140 parts of N _f N-dimethylformamide at 90 °, and a solution of 8.6 parts of 2-hydroxy-l-naphthaldehyde in 50 parts of Ν, Ν-dimethylformamide is added very slowly, with stirring Heated for 3 hours to 130 °, cooled to 5 °, the precipitate which has separated out is filtered off, washed with Ν, Ν-dimethylformamide and ethanol and dried in vacuo at 70 °. The yellow product of the formula

509851/0970

Case 150-3621

CONH

- (!! IP

melts with decomposition at 297-298 °. 7.6 parts of this product are in 75 parts of N, N-dimethylformamide heated to 130 °. 4 parts of 85 parts of nickel acetate tetrahydrate are added with stirring Ν, Ν-dimethylformamide was added dropwise, heated to 130 ° and the suspension was stirred at 130-140 ° for 4 hours.

After cooling, it is filtered off and with N, N-dimethylformamide, then washed with ethanol until the ethanol filtrate is colorless. After drying in vacuo at 70 ° becomes a red pigment of the formula

509851/0970

- 13 - Case 150-3621

obtained, the strong red colorations in paint and PVC with very good fastness properties.

Example 1

The procedure of Example 1 is followed, but 3.2 parts are used Copper acetate monohydrate, this gives the brown copper complex with an analogous structure, which is very good in lacquer Possesses fastnesses.

example

In Example 1, 2-hydroxy-1-naphthaldehyde is replaced by an equimolar amount of 3-cyano-2,6-dihydroxy-5-formyl-4-methyl-pyridine, a product of the formula is obtained in a similar manner

PONHC ₆ H ₅

which results in real red-brown colors in paint and PVC.

097Q

- 14 - Case 150-3621

Example 4

In Example 1, the 5,6-diaminobenzimldazolone is replaced by 16.2 parts of o-phenylenediamine, a product of the formula is initially obtained in an analogous manner

CONHC ^ H ₁ ο i

as an intermediate.

8.9 parts of this product are dissolved in 640 parts of ethanol with heating, very slowly with a suspension of 5.3 parts of 3-cyano-2,6-dihydroxy -5-formyl-4-methyl-pyridine is added to 200 parts of ethanol and the mixture is heated to the boil. After stirring for 30 minutes 7.5 parts of nickel acetate tetrahydrate in 280 parts of ethanol are slowly added at reflux. The reaction mixture is stirred for a further 6 hours at reflux / cooled, filtered off with suction and washed with ethanol. After drying in vacuo at 70 °, an orange-yellow pigment of the formula

CONHCH,

509851/0 970

- 15 - Case 150-3621

which has very good fastness properties in paint and PVC.

example

In Example 4, the oc-ethoxymethylene acetoacetanilide is replaced by 2,5-dimethoxy-ot-aethoxymethylene acetoacetanilide, this gives a yellow pigment of the formula

Οζ

CONH

which has excellent fastness properties in lacquer and PVC.

example

A solution of 35.6 parts of 3-cyano-2,6-dihydroxy- -5-formyl-4-methylpyridine in 145 parts of dimethylformamide slowly becomes a solution of 21.6 parts of o-phenylenediamine added in 140 parts of dimethylformamide. The mixture is then stirred for 3 hours at boiling temperature,

509851/0970

- 16 - Case 150-3621

cooled, the precipitate filtered off, washed with ethanol and dried in vacuo at 80 °. The thus obtained Product of the formula

melts with decomposition at 271-274 °. A solution of 11.7 parts of a-ethoxymethylene-acetoa'cetanilid in 40 parts of dimethylformamide is at 100 ° to a suspension of 13.4 parts of the above Compound in 95 parts of dimethylformamide was slowly added. It is heated to 100 ° for 30 minutes stirred at this temperature, slowly with a solution of 12.5 parts of nickel acetate tetrahydrate in 115 Parts of dimethylformamide are added and the reaction mixture is stirred at 120 ° for 3 hours. After cooling down, the The precipitate is filtered off, washed with ethanol and dried. The product is identical to the product from example 4.

509851/0970

- 17 - Case 150-3621

APPLICATION EXAMPLE

To a base mix

63 parts of polyvinyl chloride emulsion, 32 parts of dioctyl phthalate,

3 parts of commercially available epoxy plasticizer, 1.5 parts stabilizer (barium-cadmium complex,

also commercially available) and 0 _f 5 parts of a chelator (commercially available)

0.5 parts of the pigment according to Example 1 and parts of titanium dioxide pigment are added and intimately with one another mixed. The mixture is heated to 160 ° in a mixer with friction rollers (one roller with 20, the other with 25 revolutions per minute) for better pigment distribution for 8 minutes and then peeled off the 0.3 mm film obtained, which has a red shade. The coloring is great good light- and migration-fast, as well as heat-resistant.

The table below shows further pigments of the formula Ia which are analogous to the working instructions of Examples 1 to 6 can be prepared. R corresponds to hydrogen in all cases, only in the example 50 it's methyl.

& ÜU8R1 / 0970

Tabel

Ex. No.

10

11

12th

13th

14th

10

-NHC, H_ 6

do.

-NH

-NH H ₃ CO

do.

-NHCH

6th

do.

-NH H ₃ CO

11

do.

do.
do.

do.
do.

12th

-CH = CH

do.

do.

do.

-CH = CH-CH = CH-

-C = CH I COOH

-C = N OH * '

do.

Ni do.

do. do do. do.

Nuance in PVC

orange

do.

reddish yellow

orange

reddish yellow

orange

yellow

reddish yellow

«V?

Ni CO

cn

Table (continued)

Ex. No.

15th

16 17

18 19

20 21

22 23

-NH ^H 3 ^C0 '

~ NHC, H_

do.

do.

do.

do.

do.

-NH H ₃ CO

H ₃ CO

11

do.
do.

Cl

HOqU-Tz-V

[δ

do.

12th

-N

N »C ι CH"

do.

* C - CO * ~ C * I. - NH ι CN CH.

do. do.

do. do.

do. do.

do. Cu

Ni do.

do. do.

do. do.

Nuance in PVC

yellow-brown

do. do.

orange do.

reddish yellow orange

yellow reddish yellow

Table (continued)

Ex. No.

24

25 26 27

28

29 30

31

32 33

34

10

H ₃ CO

-NH-

-CH ₃ -OCH,

OC ₂ H ₅

—NH "

-NHCOCH ₁ .

CONHC ^ H-

11

do. do.

do.

do.

do. do.

NH O Y CO ^ NH ^ do • do • do

12th

-C = C - CO 1
CH CN

do.

do.
do.

do.

do.
do.

do.

do.
do.
do.

NH

Me,

Ni

do. do. do.

do.

do.

do.

do.

do. do. do.

Nuance in PVC

reddish yellow

do. do. do.

do.

do. do.

do.

do. do. do.

Table (continued)

cn
ο
to
oe>

Ex. No.

37 38

39 40

41 42

NHC-H ₁ . D.

NH- <g) -CH ₃

NHC, H_ 6

do.

11

CH

-NH

-NH

OCH,

HOOC

Cl

HO

NC

12th

-C -C-CO-II

CH CN

do.

NH

-CH-CH

OJ

do. do.

-C-CH-CH-CH-o OCH "

-CH-CH ^ -C-CH '

-C-CH-C-CH- II

Cl Cl

do. do.

do. do do do.

Nuance in PVC

reddish yellow do.

orange do.

Red

reddish yellow

do. do.

CO

cn

Table (continued)

in
ο
co

E.g.

No.

43

44

45

48

49

50

10

OC ₂ H ₅

- NH - / ÖV CONH -fps- OCH H CO ^ --Ί3γ

-NH- (O) -NHCO-

-NHCH,

-NHC ₂ H ₅

Br

-NHC.H _c ο

11

Br Br

do.

^H 3 ^COOC TO]

H ₃ CO ₁ Q ₁

12th

-C-CH-CH = CH-1
Cl

-C = CH-CH = CH- i
Br

-C = C - CO -

! I.
CH CN

do.

do.

NH

Me-

Ni

do.

• do.

do

do.

do.

do.

do.

Nuance in PVC

reddish yellow

do.

do.

do.

do.

do.

do.

do.

cn J ₃ N) S co ^

■ ο cn

Claims (13)

- 23 - Case 150-3621 claims 1. The compounds of the formula (I) (D, where R is alkyl, R_ alkylcarbonyl, alkoxycarbonyl or a Group of the formula -CONR R, R hydrogen or alkyl, R is a bonded in the ortho or peri position carbo- or heterocyclic radical of aromatic character, R used to complete a carbo- or heterocyclic ring of aromatic character necessary atomic group j R_ hydrogen or alkyl, R_ hydrogen, alkyl or a single or binuclear carbo- or heterocyclic radical of aromatic character and Me is a divalent transition metal atom or zinc mean, whereby all mentioned residues of aromatic character are those in the chemistry of pigment dyes usual substituents, including a carboxyl group in the molecule and fused rings, can carry. 509851/0970 Case 150-3621 2. The compounds according to claim 1 of the formula Ia where R, 10 11 (Ia), Hydrogen or methyl, ■ C1-4 alkyl or C1-4 alkoxy or a Group of the formula -NH R,. ,, 1,2-phenylene that has up to two substituents can carry 1,2-, 2,3- or 1,8-naphthylene, 9,10-phenanthrylene, 5,6-acene aphthenylene or a residue of the formula or R ^ 2 one optionally up to two substituents bearing radical of the formula -CH = CH-CH = CH- or -CH = CH- -NH-CO-C --C-, ι f CN R ₁₄ or a residue of the formula -C =
I.
OH or -N-N = C- Ks Ka where the marked with * Atom is bonded to the carbon atom, which in turn is bonded to oxygen, 509851/0970 - 25 - Case 15O-3621 R ₁₃ is hydrogen, C, _ ₄ alkyl, naphthyl, benzimidazolonyl-5, or phenyl which optionally bears up to three substituents, including up to three methyl, up to two selected from the group chlorine, bromine, nitro and C, --Alkoxy and / or from the group C ₁ _ ₂ alkyl-carbonylamino, benzoylamino optionally further substituted and optionally further substituted phenylaminocarbonyl,
R .. methyl or phenyl, R _{5 is} hydrogen, methyl or phenyl and Me _{1 is} nickel, copper, zinc or cobalt and the aromatic nuclei, where indicated, can have one or two substituents, including up to two from the group consisting of chlorine, bromine, methyl, C , ₂ ~ alkoxy and nitro and / or one from the group consisting of cyano, hydroxy, alkoxycarbonyl, aminocarbonyl, C ₁ "-alkylaminocarbonyl, di-C ₁ " -alkylaminocarbonyl, di-C ₁ "-alkylaminocarbonyI, carboxyl, phenyl and phenoxy. 3. The compounds according to claim 1 of the formula I b (I b) wherein A is methyl, C _1-3 -AlkOXy, amino, C. ^ - alkylamino or benzimidazolonyl-5-amino or optionally up to three substituents, including up to three methyl, up to two the end 50 ü 351/0070 - 26 - Case 150-3621 from the group chlorine, bromine, nitro and _3-3 and / or one from the group C -alkylcarbonylamino, phenylcarbonylamino and phenylaminocarbonyl bearing phenylamino, the first two phenyl nuclei bearing up to two substituents from the group chlorine, bromine and C.-alkoxy can, -X- JL B 1,2-phenylene, which has up to two substituents including up to two from the group consisting of chlorine, bromine, methyl and C -alkoxy and / or one Can carry cyano, hydroxy, nitro, C -alkoxycarbonyl, aminocarbonyl or carboxyl group, 2,3-dihydroxyquinoxalinylene-6,7 or benzimidazolonylene-5,6, D is a radical of the formula -CH = CH-CH = CH-, the one or two substituents, including up to two chlorine, bromine or methoxy and / or can carry a nitro or a remainder of the Formula -C = Nf ^ -C = C - CO - NH -, 1 IUJ 'II OH * ^^ CH CN -NN = CI j or C ₆ H ₅ CH ₃ a hydrogen or a carboxyl group, b hydrogen, chlorine, bromine or nitro and > Me2 nickel or copper
mean. 4. The compounds according to claim 1 of the formula Ic 50985 1/0 97 0 - 27 - Case 150-3621 wherein A _{1 is} benzimidazolonyl-5-amino or optionally up to three substituents, including up to three methyl, up to two from the group consisting of chlorine, bromine, nitro and C 1 -alkoxy and / or one from the group C 1 -alkylcarbonylamino Phenylamino, phenylcarbonylamino and phenylaminocarbonyl, where the first two phenyl nuclei can carry up to two substituents from the group consisting of chlorine, bromine and C, ^ -alkoxy, B ₁ ortho-phenylene, which has a substituent from the group of chlorine, bromine, methyl, methoxy and nitro can carry, or benzimidazolonylene-5,6, D _{1 is} a radical of the formula -CH = CH-CH = CH-, -C = KT ^ i '-C = C - CO - NH . -IvJJ II OH ^^ CH ₃ CN -C = CH-J ^ i _{or cr} _ _{CH = CH} COOH and Me_ mean nickel or copper. 50985 1/0970 - 28 - Case 150-3621 5. The compounds according to claim 1 of the formula Id (Id), wherein A _{2 is} phenylamino, which optionally bears a substituent from the group consisting of chlorine and methyl and / or two methoxy groups in the 2,5-position, B is ortho-phenylene, which has a substituent from the group consisting of chlorine, methyl or methoxy can carry, or benzimidazolonylene-5,6, D_ a remainder of the. Formula -C = ι COOH ~ ^{C = N} -r ^ i or -C = C - CO - NH OH £ ^> CH ₃ CN and Me ₂ mean nickel. 6. Process for the preparation of the compounds of the formula I. according to claim 1, characterized in that a compound of formula II (II), or one of its tautomeric forms, with a salt of a divalent transition metal atom or of zinc metallized. 509851/0970 - 29 - Case 150-3621 7. Process for the preparation of the compounds of the formula I or II according to claim 6, characterized in that one mole of a diamine of the formula III H ₀ N - R. - NH_ (III) JL £ 4 with one mole of an ortho-hydroxyaldehyde of the formula IV and with one mole of a compound of formula V R. (V) where R _{0 is} alkyl or hydrogen, ο condensed, the condensation in the presence or absence of a salt of a divalent transition metal or of zinc. 8. Process for the preparation of the compounds of the formula I or II according to claim 6, characterized in that that one mole of a compound of the formula IV with one mole of a compound of the formula VI 509851/0970 - 30 - Case 150-3621 optionally condensed in the presence of a salt of a divalent transition metal atom or of zinc. 9. Process for the preparation of compounds of the formula VI according to claim 8, characterized in that one one mole of a compound of the formula III according to claim 7 with one mole of a compound of the formula VII (VII), = 0 ^R l where R _{0 is} alkyl or hydrogen, condensed. ο 10. pie compounds of the formula II according to claim 7. 11. The compounds of the formula VI according to claim 9. 12. The use of the pigment dyes of the formula I. according to claim 1 for coloring solvent-free and solvent-containing plastic compositions. 13. The plastic compositions colored with the pigments of the formula I according to claim 1. 3700 / HW / VS / HSc SANDOZ-PATENT-GMBH 509861 / fj 970 'MC \ *! aJ \ \ Ut '* -