DE2255525C3 - Diaminopyrimidine dispersion azote substrates, process for their preparation and their use - Google Patents

Description

D-N = N

characterized in that one compounds of the general formula

CN

r ^N

H ₂ N

D-N = N-CH

CN

with amidines of the general formula
NH

B-C

H, N

wherein B benzyl, phenylethyl or optionally methyl, ethyl, methoxy, ethoxy, chlorine or nitro substituted phenyl.

2. Dyestuffs according to Claim 1 of the general formula

35 NH ₂

converts, where in the formulas B and D have the meaning given in claim 1.

5. The use of the dyes according to claim 1 or 2 for dyeing textile material made of acrylonitrile polymers, polyamides, cellulose esters and polyesters.

40

in which one X is NH ₂ and the other X is a radical B, B benzyl, phenylethyl or optionally phenyl substituted by methyl, ethyl, methoxy, ethoxy, chlorine or nitro, Y nitro, cyano, chlorine, bromine, carbomethoxy, carbethoxy, methylsulfonyl, Ethylsulfonyl, methyl, methoxy, phenylazo, p-nitrophenylazo, p-hydroxyphenylazo, p-methoxyphenylazo, p-chlorophenylazo or methylphenylazo, Y ₁ hydrogen, nitro, chlorine, bromine, cyano, methyl, methoxy, carbomethoxy, carbethoxy or ethyl and methylsulfonyl Y _{2 is} hydrogen, chlorine, bromine, cyano, methyl, methoxy, carbomethoxy or carbethoxy.

3. Process for the preparation of dyes according to claim 1, characterized in that one diazonium compounds of amines of the general formula

D-NH,

with coupling components
formula

Η — Α

The invention relates to diaminopyrimidine dispersion azo dyes of the general formula I.

D-N = N-A (I)

in which D is the remainder of a heterocyclic diazo component or a substituted diazo component of the aniline series, A is a radical of the general formula

or

(Ha)

(Hb)

60

the general

converts, where in the formulas A and D have the meaning given in claim 1.

wherein B benzyl, phenylethyl or optionally methyl, ethyl, methoxy, ethoxy, chlorine or Is nitro-substituted phenyl.

Diazo components are in particular substituted anilines and amino compounds of the benzothiazole,

Jenzisothiazole, thiazole, thiadiazole thiophene, triizole, Benztriazole, indazole or pyrazole series.

As a substituent for the radicals D of the diazo groups include, for example:

In the benzene series, chlorine, bromine, nitro, cyano, rrifluonnethyl, methylsulfonyl, ethylsulfonyl, phenyläulfonyl, p - {/ i-hydroxyethyl) phenylsulfonyl, carbomethoxy, Carboethoxy, carbobutoxy, carbo- / i-methoxy-ethoxy, Carbo-pt-ethyl-hexoxy, Carbo - ^ - hydroxyethoxy, optionally N-mono- or N-disubstituted carboxylic or sulfonamide, methyl, ethyl, methoxy or ethoxy and phenylazo.

N-substituents of the carbon or sulfonamides are e.g. methyl, ethyl, propyl, butyl, ff-ethylhexyl, Cyclohexyl, benzyl, phenylethyl, / f-hydroxyethyl, / i-hydroxy-propyl, // - methoxy-ethyl, y-methoxy-propyl or y-ethoxypropyl and the pyrrolidide, Piperidide or morpholide.

In the azobenzene series, chlorine, bromine, nitro, cyano, carbomethoxy, carboethoxy, methyl, ethyl, methoxy, Ethoxy, hydroxy, acctylamino, formyl, / i-hydroxy-ethoxy or ethoxycarbonylamino.

In the heterocyclic series chlorine, bromine, nitro, cyano, methyl, ethyl, phenyl, methoxy, ethoxy, Methyl mercapto, ii-carbomethoxy-ethyl mercapto, / i-Carboäthoxyäthylmercapto, Carbomethoxy, Carboäthoxy, Acetyl, methylsulfonyl or ethylsulfonyl.

The remainder D is derived z. B. from the following amines:

o-, m- or p-nitroaniline. ^ ₀

o-, m- or p-cyananiline,

2,4-dicyaniline,

o-, m- or p-chloroanilir>,

3,4- or 2,5-dichloroaniline,

2,4,5- or 2,4,6-trichloroaniline, o-, m- or p-bromoaniline.

2,4,6-tribromaniline,

2-chloro-4-nitroaniline.

2-bromo-4-nitroaniline,

2-cyano-4-nitroaniline, 2-methylsulfonyl-4-nitroaniline, 2-methyl-4-nitroaniline,

2-methoxy-4-nitroaniline,

4-chloro-2-nitroaniline,

4-methyl-2-nitroaniline, 4-methoxy-2-nitroaniline,

l-amino-l-trifluoromethyl ^ -chlorobin / ol, 2-chloro-5-amino-ben7onitrile,

2-amino-5-chlorobenzonitrile,

1 -amino-2-nitrobenzene-4-sulfonic acid-n-butyl-

amide or - / i-methoxyethylamide, 2,4-dinitroaniline,
2,4-dinitro-6-chloroaniline,
2,4-dinitro-6-bromaniline,

2,4-dinitro-6-cyananiline, l-amino-2,4-dinitrobenzene-6-methylsulfone, 2,6-dichloro ~ 4-nitroaniline,
2,6-dibromo-4-nitroaniline,
2-chloro-6-bromo-4-nitroaniline, 2,6-dicyano-4-nitroaniline, 2-cyano-4-nitro-6-chlorani 1 in, 2-cyano-4-nitro-6-bromaniline, 1 - Aminobenzene-4-methylsulfone, 1-amino-2,6-dibromobenzene-4-methylsulfone. 1 -amino ^ .o-dichlorobenzene ^ -methylsulfone, l-amino-2,6-dinitrobenzene-6-carboxylic acid

methyl ester or - ^ i-melhoxyethyl ester. S.S-dichloro-anthranilic acid propyl ester.

3,5-dibromo-anthranilic acid - ^ - methoxyethyl ester,

N-benzoyl-p-phenylenediamine, N-acetyl-p-phenylenediamine, N-phenyl-sulfonyl-p-pheuylenediamine, N-phenyl-sulfonyl-m-phenylenediamine, ^ -Amino-acetophenone, 4- or 2-amino-benzophenone, 2-aminodiphenyl sulfone, 2-, 3- or 4-aminobenzoic acid methyl ester, ethyl ester,

-propylester,

-butyl ester,

-isobutyl ester, - ^ - ethylhexyl ester, -cyclohexyl ester, -benzyl ester,

-phenyl ester,

- / i-methoxyethyl ester, - / j-ethoxy-ethyl ester, - / j-butoxy-ethyl ester, -methyl diglycol ester, ethyl diglycol ester, methyl triglycol ester, -ethyl-triglycol ester, -ß-hydroxyethyl ester, - / (- acetoxyethyl ester, -ii - (/ i'-hydroxy-ethoxy) -äthyles \ er, - / i-hydroxy-propyl ester, -y-hydroxy-propyl ester, -ω-hydroxy-butyl ester,

- ((i-hydroxy-hexyl ester, 5-nitro-anthranilic acid methyl ester, isobutyl ester, methyl diglycol ester, - / i-methoxy-ethyl ester, - / i-butoxy-ethyl ester,

- / i-acetoxy-ethyl ester, 3- or 4-amino-phthalic acid-, 5-amino-isophthalic acid or amino-terephthalic acid dimethyl ester, -di-ethyl ester,

-di-propyl ester,

-di-butyiester, 3- or 4-aminobenzoic acid amide, -methylamide,

-propylamide,

-butylamide,

-isobutylamide, -cyclohexylamide, - / i-ethyl-hexylamide, - / - methoxy-propylamide, -y-ethoxy-propylamide,

-anilide,
2-, 3- or 4-amino-benzoic acid-dimethylamide.

-diethylamide,

-pyrrolidide.

-morpholide.

N-methyl-N - ^ - hydroxy-ethylamide, 5-amino-isophthalic acid diamide,

-bis -) - methoxy-propylamide, aminoterephthalic acid-bis-diethylamide, 3- or 4-amino-phthalic acid imide, - / i-hydroxy-ethyl-imide, -y-hydroxy-propylimide, -phenylimide,

-p-tolylimide,
3-amino-6-nitro-phthalic acid / i-hydroxyethylimide,

2-, 3- or 4-amino-benzoic acid dimethylamide,

-diethylamide,

-pyrrolidide,

-morpholide,

-N-methyl-anilide,
Methylsulfonic acid-2'-, -3'- or

^ '- aminophenyl ester,
Ethylsulfonic acid-2'-, -3'- or

^ '- amino-phenylester-,
Butylsulfonic acid-2'-, -3'- or

^ '- aminophenyl ester,
Benzenesulfonic acid-2'-, -3'- or

^ '- aminophenyl ester,
3- or 4-aniinodiphenylene oxide, 2-amino-benzothiazole,
2-Amino-6-methylsulfonyl-benzothiazole, 2-amino-6-nitro-benzothiazole, 5,6- or 6,7-dichloro-2-aminobenzothiazole, 4-amino-5-br <Mn-7-nitro -1,2-benzisothiazole, 3-amino-5-nitro-2, l-benzisothiazole, 3-amino-5-nitro-7-bromo-2,] - benzisothiazole, 2-amino-thiazole,
2-amino-5-nitro-thiazole,
2-amino-4-methyl-thiazole-5-carboxylic acid

ethyl ester,
2-amino-4-methyl-5-acetyl-thiazole,

4 '- {ethoxycarbonyl-am; no) -2-methyl-4-amino-

azobenzene,

2,5-dimethoxy-4-aminoazobenzoI,
4'-chloro-2,5-dimethoxy-4-aminoazobenzoI,
4'-nitro-2,5-dimethoxy-4-aminoazobenzene,
4 '- {Hydroxyethoxy) -2,5-dimethoxy-4-amino-

azobenzene,

4'-chloro-2,5-dimethyl-4-aminoazobenzene,
4'-methoxy-2,5-dimethyl-4-aaiinoazobenzene,
4'-nitro-4-aminoazobenzene,
3,5-dibromo-4-aminoazobenzene,
2,3'-dichloro-4-aminoazobenzene,

1 - phenylazo-4-aminonaphthalene,
l-Phenylazo-S-ethoxy- ^ aminonaphthalene.

To prepare the dyes of the general formula I can be a diazonium compound of Amines of the general formula III

D-NH ₂

(III)

with coupling components of the general formula IV

HA

(IV)

acid esters,

2-phenyl-5-amino-1,3,4-thiadiazole, 3-methylmercapto-5-amino-l, 2,4-thiadiai.ol, S-ff-carbomethoxy-ethylmercapto-S-amino-

1,2,4-thiadiazole,
3-amino-1,2,4-triazole,
4-amino-7-nitro-benzotriazole, 3-amino-indazole,
3-amino-5-chloro-indazole,
3-amino-5-nitro-indazole,
1 -benzyl-5-amino-pyrazole,
1 - phenyl-5-aminopyrazole.

Suitable diazo components of the aminoazo series are, for example:

4-aminoazobenzene,

2,3-dimethyl-4-aminoazobenzene, 3,2-dimethyl-4-aminoazobenzene, 2,5-dimethyl 1-4-aminoazobenzene, 2-methyl-5-methoxy-4-aminoazobenzene, 2-methyl-4 ', 5-dimethoxy-4-aminoazobenzene, 4'-chloro-2-methyl-5-methoxy-4-aminoazobenzene, 4'-nitro-2-methyl-5-methoxy-4-aminoazobenzene, 4'-hydroxy-2-methyl-5-methoxy-4-aminoazo-

benzene,
4 '- (^ - Hydroxyethoxy) -2-methyl-5-methoxy-

4-aminoazobenzene,
4'-hydroxy-2,2'-dimethyl-5-methoxy-4-aminoazobenzene,

4'-hydroxy-4-aminoazobenzene, 4'-hydroxy-2'-methyl-4-aminoazobenzene, 4'-hydroxy-3'-methyl-4-aminoazobenzene, 2-hydroxy-5'-methyl-4-aminpazobenzene, 4'-hydroxy-2-methoxy-4-aminoazo benzene, 4-hydroxy-2'-chloro-4-aminoazobenzene, 4'-hydroxy-2,5-dimethoxy-4-aminoazobenzene 7.ol. 4'-Hydroxy-2,6-dichloro-4-aminoazobenzene. 4-hydroxy-3-methoxy-4-aminoazobenzene. 4'-chloro-2-methyl-4-aminoazobenzene, 4'-formyl-2-methyl-4-aminoazobenzene.

implement, where D and A have the meaning given above.

The amines are diazotized as usual. The coupling is also as usual in aqueous Medium, optionally with the addition of solvents, in the case of a weak to strongly acidic reaction accomplished.

To prepare the coupling components of the formula IV, compounds of the formula Va

or Vb q

Cl
B.

Cl

(Va)

(Vb)

react with ammonia. For the synthesis of coupling components of the formula lib you can also z. B. Compounds of Formula VII

-N _v

= -N

SR ₃

(VII)

HO

in which R _{1 is} preferably methyl or ethyl, with ammonia to form 2-amino-4-hydroxypyrimidine derivatives of the formula VIII

<f ^ NH ₂ (VIII)

γ _Ν

HO
implement. Compounds of Formula VIII are also

accessible from guanidine and / f-ketoesters. the Hydroxyl group in the intermediate products VIII can be removed by the usual reagents, such as. B. phosphorus oxychloride, exchange for a chlorine atom, which can then be displaced by ammonia.

In the preparation of the coupling components of the formula IV by reaction with ammonia it is advisable to use solutions of the ammonia in solvents which are inert under the reaction conditions to use. Depending on the reaction temperatures, water, methanol, ethanol, ethylene glycol, Ethylene glycol mono- or dimethyl ether, dimethylformamide or N-methylpyrrolidone can be considered. But you can also work with liquefied ammonia under pressure without a solvent.

It is expedient to use to bind the hydrogen chloride released during the reaction Excess amine or the commonly used acid-binding agents such as tertiary Amines, magnesium oxide or alkalis.

The dyes of the formula I according to the invention with a radical of the formula Ha can also be used thereby produce that a compound of formula IX

/
DN = N-CH

CN

CN

with amidines of the formula X

B-C = NH

NH,

(IX)

(X)

implemented according to methods known per se. Details of the preparation can be found in the examples.

Dyes of the general formulas I a and I b are particularly useful industrially

H, N

(la)

(Ib)

in which B benzyl phenylethyl or phenyl optionally substituted by methyl, ethyl methoxy, ethoxy, chlorine or nitro, Y nitro, cyano, chlorine, bromine, carbomethoxy, carbethoxy, methyl sulfonyl ethyl sulfonyl MeAyL methoxy, phenylazo, p-nitrophenylazo, p-nitrophenylazo -Methoxyphenyl-32X3, p-chlorophenyiazo or methylphenylazo, Y ¹ hydrogen, nitro, chlorine, bromine, cyano, methyl, medioxy, carbomethoxy, carbethoxy, methylsttlfonyl or ethyl sulfonyl and Y ₂ hydrogen, chlorine, bromine, cyano, methyl methoxy or, carbomethoxy Carbäihoxy is.

Furthermore, the corresponding dyes, which may be used as diazo components, are particularly valuable by nitro, chlorine, bromine, cyano, methyl, methyl mercapto, / i-carbomethoxy-ethyl mercapto, ß-carboethoxy-ethyl mercapto, Carbomelhoxy, carboethoxy or acetyl substituted benzothiazole, benzisothiazole, Contain thiazole, thiadiazoi or thiophene.

Some of the particularly valuable diazo components are:

4-nitro-aniline,

2-chloro-4-nitro-aniline,

2-bromo-4-nitro-aniline,

2-cyano-4-nitro-aniline,
2-methoxy-4-nitro-aniline,

2-amino-5-nitro-phenylsulfonic acid dimethylamide,

2-Amino-5-nitro-phenylsulfonic acid-butylamide, 2-amino-5-nitro-phenylsulfonic acid- / i-methoxyethylamide,

2-amino-benzonitrile,

3-chloro-4-aminobenzonitrile,

2-chloro-5-aminobenzonitrile,

2-amino-5-chlorobenzonitrile,
2,5-dichloro-4-aminobenzonitrile, 1-amino-2,4-dicyanobenzene,

l-amino-2,4-dicyano-6-chlorobenzene, 2-chloro-4-amino-5-nitro-benzonitrile, 2-amino-3-chloro-5-nitro-benzonitrile, l-amino-S-bromo-S-nitro-benzonitrile, 2,6-dicyan-4-nitro-aniline,

2,5-dichloro-4-nitro-aniline,

2,6-dichloro-4-nitro-aniline,

2,6-dibromo-4-nitro-aniline,
Z-chloro-o-bromo- ^ nitro-aniline, 2,4-dinitro-aniline,

2,4-dinitro-6-chloro-aniline,

2,4-dinitro-6-bromo-aniline,

2-amino-3,5-dinitro-benzonitrile, 1-amino ^ -nitrobenzoW-methylsulfone, l-amino-4-nitrobenzene-2-ethylsulfone, 4-methylsulfonyl-aniline,

l-Amino ^ -chlorbenzoM-methylsulfone, l-amino-2,6-dibromobenzene-4-methylsulfone, 1-amino ^ o-dichlorobenzoM-methylsulfone, 4-aminobenzoic acid ester,

2-amino-5-nitro-benzoic acid ester, 2-amino-3-chloro-5-nitro-benzoic acid ester, 2-amino-3,5-dichloro-benzoic acid ester, 2-amino-3,5-dibromo-benzoic acid ester,

2-Amino-3,5-dinitrobenzoic acid methyl ester or -fi-methoxy-ethyl ester,

Amino-terephthalic acid diethyl ester, 4-amino-azobenzene,
23'-Dimethyl-4-aniino-azobeai2oL 2 ', 3-Dimethyl-4-amino-azobenzene, 2,5-Dimethyl-4-amino-azobenzoL 4'-Hydroxy-2'-methyI-4-a ^ nino- azobenzene, 3,5-dibromo-4-amino-azobenzoL, 2-methyl-5-methoxy-4-amnio-azobenzoL

4'-chloro-2-methyl-5-methoxy-4-aminoazobenzoL

4-Nitro-2-Biethyi-5-methoxy-4-aniJnoazobenzene
4'-nitro-2 ^ -dimethoxy-4-aniino-a2obeazoL

Of the particularly valuable heterocyclic diazo component € D, the following should be mentioned:

708610/239

\O

2-amino-thiazole,
2-amino-5-nitro-thiazole,
I-Amino- ^ methyl-S-nilro-thiazole, 2-Amino-4-methyl-thiazoI-5-carboxylic acid ethyl ester,

l-Amino-'t-methyl-S-acetyl-thiazoI, 2-amino-5-phenyl-1,3,4-thiadiazole, 3-phenyl-5-amino-l, 2,4-thiadiazole, S-methylmercapto-S-amino-l ^ -thiadiazole, S - ^ '- Carbomethoxy-ethylmercapto-S-amino-

1,2,4-thiadiazole,
S-zf-carbathoxy-ethylmercapto-S-amino-

1,2,4-thiadiazole,
2-Amino-6-nitro-ben7thiazole, 2-Amino-3-cyano-4-methyl-thiophene-5-carbon ester,

3-amino-5-nitro-2,1-benzisothiazole, 3-amino-5-nitro-7-chloro-2,1-benzisothiazole, 3-Amino-5-nitro-7-bromo-2,1-benzisothiazole, 4-amino-7-nitro-1,2-benzisothiazole, 4-Amino-5-bromo-1,2-benzisothiazole, 4 ^ 01 ^ 0-5- ^ 01 ^ 7- ^ 11-0-1,2-benzisothiazole, 4-Amino-5-cyano-7-nitro-1,2-benzisothiazole.

The dyes of the invention are yellow to red and are suitable for dyeing textile materials made Acrylnitrilpolmerisaten, synthetic polyamides, Celluloseestern such as 2 _'2 - or triacetate, and in particular from synthetic linear polyesters, such as polyethylene glycol terephthalate and chemically analog based polymers. In some cases, extremely strong dyeings are obtained which are distinguished by good fastness properties, in particular light fastness.

The data on parts and percentages in the following examples relate to the weight, if it is not otherwise noted.

Compared to connections that are known from DT-AS 10 72 222 and DT-OS 16 44 245, the dyes according to the invention have advantages in particular in terms of color strength and freshness Behavior. In view of the structural differences, the replacement of a C - N bond with a C - C bond, these advantages are very surprising to this extent.

trium methylate (30%) heated to boiling for 4 hours in 100 parts by volume methane. After the cold egg of the reaction mixture becomes the dye of the form

COOCH ₃ H ₂ N

H, N

filtered off and washed with methanol and water. When coloring on materials made of polyethylene glycol terephthalates give yellow shades with good fastness properties.

Example 2

Concentrate in an ice-cold mixture of 74 parts trated sulfuric acid and 26 parts of nitrosylsulfuric acid carry 14.2 parts of 2-amino-5-nitro-benzo nitrile and stir the mixture under good cooling for 6 hours. The clear diazonium salt solution will then in portions in a mixture of 15 parts of 2-phenyl-4,6-diamino-pyrimidine, 100 parts by volume of glacial acetic acid and 600 parts by volume of ice water are added, the pH of the solution being adjusted by adding sodium acetate is held at about 2 to 3. After coupling is complete, the dye of the formula

H, N

Example 1 Anthranilic acid methyl ester

45 isolated by filtration, washed with water and dried. A red-brown powder is obtained which produces strong orange tones with a high level of fastness on polyester fibers.

The 2-phenyl-4,6-diaminopyrimidine required for coupling is obtained by adding 56 parts of 2-phenyl-4,6-dichloro-pyrimidine heated with 150 parts of a concentrated aqueous ammonia solution in an autoclave at 180 ° C. for 14 hours. After cooling, the reaction product is filtered off with suction and im Vacuum dried.

Example 3

4.5 parts of 2-amino-5-chlorobenzonitrile are diazotized with sodium nitrite in a conventional manner in a mixture of 200 parts by volume of ice water and 10 parts by volume of concentrated hydrochloric acid. The clear diazonium salt solution is then added to a mixture of 500 parts of ice and 5.6 parts of 2-pbenyl-4,6-diaininopyrimidine, which had previously been poured into 100 parts of formamide. The Kupplang is at pH 4 Ms 5 inaerMb terminated a short time, which is excreted Far & STRF isolated by filtration the compound whose _TO composition of the formula

CN, -N = N- ^ ~ ^1N vy

Then filtered off, washed with water and im

Vacuum dried. ,

Azo compounds obtained in this way become H ₂ N

Bit 7.7 parts p-CMorbeözäaudia and 5 parts Ma- corresponds, dyes polyester fibers in green <3e1 & ·

15 parts of anthranilic acid methyl ester are dissolved in 200 parts by volume of water with the addition of 20 parts by volume of concentrated hydrochloric acid. It is cooled to ⁰ ° C., 32 parts by volume of a 23% strength sodium nitrite solution are added, the mixture is ^{stirred for 2 hours at 0} ° C. and a solution of 6.6 parts of malodinitrile in 50 parts by volume of ethanol is then added dropwise. To complete the coupling, the pH of the mixture is adjusted to 5 and the precipitated product of the formula

JOOCaFi ₃

11th

12th

tones with excellent fastness to light and theimos.

A dye of the same formula is obtained

also by implementing 5.7 parts of the coupling ""

Product of 2-amino-5-chlorobenzonitrile and malo-5

dinitrile with 7.8 parts of benzamidine hydrochloride

Presence of 10 parts of sodium methylal (30%) in

the procedure given in Example 1. ■ ■, g μ

Following the procedure described, ²

also produce the dyes described in the following io
Table listed are:

Color of the coloring on polyester

SO ₂ -NH-C ₂ H ₄ -O-CH ₃

COOCH ₃

H ₂ N

"5

H ₂ N

14 O ₂ N

15 O, N

COOCH ₃

At- D

Hue of Coloration on polyester

Br

CN

orange

orange

orange

CN

16 O ₂ N

O ₂ N

NO ₂

NO,

Cl

O ₂

O ₂ I

O ₂ N

CH ₃

SO ₂ -CH ₃

greenish
yellow

yellow

yellow

orange

orange

orange

orange

orange

orange

Cl CN

17 Ο, Ν

Br

Cl

O ₂ Ν

α Br

19 0, N-

Br Cl

20 O ₂ N-

Br NO ₂

21 O ₂ N- ^

O ₂ N

NO ₂

scarlet

scarlet

orange

orange

orange

Red orange

rotofang

13th

KJ VJ \ J 14th

Continuation of example no.

23 O, N

NO,

Br

24 cl

NC

y ν

Cl

Cl Cl

NO,

27 NC

Cl

SO ₂ -CH ₃

28 O ₂ N-

Cl

Cl

H ₃ CO ₂ S

COOCH ₃

_Be j. _D.

game

No color shade on polyester *

33

Red orange

15th

orange

45

39

yellow

yellow

COOC ₃ H ₇

Cl

COOCH ₃

(), N — ί

green-
pithy
yellow 20th 35 ^ =, -
I.
NO ₂
H ₅ C ₂ OOC COOC ₂ H ₅ H ₃ COOC green
pithy
yellow 25th ■ ty-
COOCH ₃ 36 Q-
0 = <> 0 green
pithy
yellow 30th 37 C. orange 35 : ₂ H ₄ -oh 40

H ₅ C ₂ OOC

3J H ₅ COOC- ^ V- yellow

COOC ₂ H ₄ -OCH ₃ 32 Q ^ - ^ ~ \ - orange

55

te H ₃ C

H ₃ COOC-H ₄ C ₂ -S
40

^ v

H ₃ C ^, CN

H ₅ C ₂ OOC

Hue <color out on polye

yellow

oranges

yellow

yellow

yellow

orange

orange

golden yellow

orange

Red

15th

continuation

Example

Color shade on polyester

Red

example

4.5 parts of 2-amino-5-chlorobenzonitrile are in a mixture of 200 parts by volume of ice water and 10 parts by volume of concentrated hydrochloric acid diazotized with sodium nitrite. The clear diazonium salt solution is there then together with 300 parts of ice to a solution of 5.6 parts of 2,4-diamino-6-phcnyl-pyrimi-

din in 100 parts by volume of water and 30 parts by volume of 30% acetic acid. The pH of the mixture becomes set to 5 to 6 with soda and the dye of the formula

CN

Cl

H ₂ N

isolated after the reaction in the usual way. A golden yellow powder is obtained which is based on polyester materials strong and true yellow colorations produced.

The dyes in the following tables are also prepared using the method described:

CN

H, N

Cl

Vn

H ₃ N

example R. Hue of No. Coloration on polyester 50 p-chlorophenyl yellow 51 o-chlorophenyl yellow 52 p-tolyl yellow 53 p-ethylphenyl yellow 54 p-methoxyphenyl yellow 55 m-nitrophenyl yellow 56 Benzyl yellow 57 Phenethyl yellow D-N = N- ^ V- H ₂ N

example

Hue of
Coloration
on polyester

CN

yellow

CN

yellow

17th

continuation

Example no.

60

61 62 63 64 65

66

67

CN

ό-

CN

CN

Cl

CN

Cl

CN

^a ~ \ _y ~

Cl CI

Cl

Br

Br

NH ₂

NH ₂

NH ₂

NH ₂

NH,

NH,

NH,

18th

• V

NH,

NH,

/ V

J X

Cl

NO ₂

NH,

NH,

NH,

NH,

S X

Hue of the coloring on polyester

OCH ₃ yellow

yellow yellow

Cl yellow

CH ₃ yellow

OCH ₃ yellow

-CH ₃

yellow

OCH ₃ yellow

yellow

orange

OCH ₃ orange

OCH ₃ orange

orange

continuation

Example no.

CN

O ₂ N

O ₂ N-

CN

CN

NH,

NH ₂

20th

NH,

Color shade on polyester

CH ₃ orange

OCH ₃ orange

orange

y ν

NH,

NH,

X-OCH,

Red

Red

O ₂ N-

NH,

Red

COOC ₂ H ₅

H ₅ C ₂ OOC

COOC ₂ H ₅

NC ₂ H ₄ -OH

NH,

NH,

NH,

NH,

-Cl

Red

yellow

-CH ₃ yellow

-CH ₃ yellow

example

21

22nd

CH ₃

CH ₃

NH-,

NH ₂

NH ₂ NH ₂

NH,

• Χ

Cl

// V

OCH ₃

OCH ₃

CH ₃

Color of the discoloration on polyester

yellow

Red

orange

orange

orange

Claims (1)

Patent claims: 1. Diaminopyrimidine dispersion azo dyes of the general formula D-N = N-A in which D is the remainder of a heterocyclic diazo component or a substituted diazo component of the aniline series and A is a radical of the general formula H, N 4. Process for the preparation of dyes according to Claim 1 of the general formula