DE2226933C3 - Azo dyes with 2,6 diaminopyridines as coupling components, process for their preparation and their use - Google Patents

Description

A-HN

Naphthalene, diphenylene oxide, benzthiazole, benzisothiazole, Thiazole, thiadiazole, thiophene, azobenzene or anthraquinone series, X cyano or carbonamide, a remainder A

CH ₃
(CH ₂ ) "CH - QH ₅

IO

NH-A

in D the remainder of a diazo component of the benzene, naphthalene, diphenylene oxide, benzthiazole, Benzisothiazole, thiazole, thiadiazole, thiophene, azobenzene or anthraquinone series, X cyan or carbonamide, a radical A

20 CH ₃

(CH ₂ ) "CH-C ₆ H ₅

wherein η is 1 or 2, and the other radical A is hydrogen or optionally substituted by hydroxy, methoxy, ethoxy, hydroxyalkoxy with 2 to 4 carbon atoms, methoxyethoxy, acyloxy or acyloxyalkoxy with 2 to 4 carbon atoms in the alkoxy group substituted alkyl with 1 to 6 carbon atoms, the acyl groups having 1 to 4 carbon atoms.

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

D-NH ₂

with coupling components of the general formula

CH ₃
X

AHN

NHA

reacts and dyes containing hydroxyl groups, optionally esterified, D, X and A have here the meanings given for claim 1.

3. Use of the dyes according to claim! for coloring polyamides and acrylonitrile polymers or polyesters.

The invention relates to azo dyes with 2,6-diminopyridines as coupling components of the general formula

CH ₃

D-N ---- N j X

Λ HN NH Λ

in which D is the remainder of a diazo component of the Bcn / ol-, where η is 1 or 2, and the other Re * \ is hydrogen or optionally by hydroxy, methoxy, ethoxy, hydroxyalkoxy with 2 to 4 carbon atoms, methoxyethoxy, acyloxy or acyloxyalkoxy with 2 to 4 carbon atoms in the alkoxy group substituted alkyl with 1 to 6 carbon atoms, the acyl groups having 1 to 4 carbon atoms, a process for the preparation of these azo dyes, which is characterized in that diazonium compounds of amines of the general formula

D - NH ₂

with coupling components of the general formula

CH ₃

(III)

AHN

NHA

converts and esterifies hydroxyl-containing dyes, where · in the formulas D, X and A have the meanings given above, as well as the use of those mentioned above Dyes for coloring polyamides, acrylonitrile polymers or polyesters.

Compared to comparable ones from US Pat. No. 2,029,315 and German Offenlegungsschrift 1917 278 known dyes, the new dyes show advantages to an unpredictable degree in color strength, light and heat setting fastness. The brilliance of the Coloring, especially in the red color range.

The remainders D derive z. B. of amines of the benzene, benzothiazole, benzisothiazole, thiazole, Thiadiazole, thiophene, azobenzene or anthraquinone series.

The radicals D of the diazo compo-

Nents are to be mentioned, for example, in the benzene series: chlorine, bromine, nitro, cyano, trifluoromethyl methylsulfonyl, ethylsulfonyl, phenylsulfonyl, carbomethoxy, carbobutoxy, carbo - // - methoxy-ethoxy carbo - / 1- hydroxy-ethoxy, optionally N-mono- or N-disubstituted carboxylic or sulfonamide methyl, ethyl, methoxy or ethoxy.

N-substituents of the carbon or sulfonamides

are z. B. methyl. Ethyl, propyl, butyl, / f-Hy droxyäthyl, ■ / -Hydroxy -propyl,, H- Methoxy -äthyl ■■ -Mcthoxy-propyl or y-Äthoxypropyi as well as:

(S ₅ pyrrolidide, piperidide or morpholide.

In the azobenzene series: chlorine, bromine, nitro, cyano Methyl, ethyl. Methoxy or ethoxy. In the heterocyclic series: chlorine, bromine, nitro, cyano, methyl

^ thyl, Phenyl, Methciy, Äthoxy, Methylmercaplo,
- carbomethoxy - ethyl mercapto, β - carboethoxyithylmercapto, carbomethoxy, carboethoxy, acetyl,
Methylsulfonyl or ethylsulfonyl.

The remainder D is derived in detail from ζ. B. from fol- 5 send amines from:

Aniline, o-, m- or p-toluidine,

o-, m- or p-nitroaniline,

o-, m- or p-cyananiline, 10

2,4-dicyaniline,

o-, m- or p-CbJoraniline,

ο-, πι- or p-bromoaniline,

2,4,6-tribromaniline,

2-chloro-4-nitroaniline, i _S.

2-bromo-4-nitroaniline,

2-cyano-4-nitroaniline,

2-methylsulfonyl-4-nitroaniline,

2-methyl-4-nitroaniline,

2-methoxy-4-nitroaniline, 20

4-chloro-2-nitroaniline,

4-methyl-2-nitroaniline,

4-methoxy-2-nitroaniline,

l-amino ^ -trifluoromethyl- ^ chlorobenzene,

l-chloro-S-amino-benzonitrile, 25

2-amino-5-chlorobenzonitrile,

1 -Amino-2-HiIrObCnZoI- ^ SuIfOnSaUrC-

n-butylamide or - / i-methoxyethylamide,
2,4-dinitroaniline,

2,4-dinitro-6-chloroaniline, 30

2,4-dinitro-6-bromaniline,
2,4-dinitro-6-cyananiline,
l-amino-2,4-dinitΓobenzol-6-methylsulfone,
2,6-dichloro-4-nitroaniline,

2,6-dibromo-4-nitroaniline, 35

2-chloro-6-bromo-4-nitroaniIine,
2,6-dicyano-4-nitroaniline,
2-cyano-4-nitro-6-chloroaniline,
2-cyano-4-nitro-6-bromaniline,

l-aminobenzene-4-methylsulfone, 40

l-amino-2,6-dibromo-benzene-4-methylsulfone,
l-Amino ^^ - dichlorobenzoM-methylsulfone,
l-amino-2,4-dinitrobenzene-6-carboxylic acid

methyl ester or - ^ - methoxyethyl ester,
3,5-dichloroanthranilic acid propyl ester, 45

3,5-dibromanthranilic acid - ^ - methoxyethyl ester,
N-acetyl-p-phenylenediamine,
4-aminoacctophenone,
4- or 2-amino-benzophenone,

2- and 4-aminodiphenyl sulfone, .. ₅₀ 2-, 3- or 4-aminobenzoic acid methyl ester,

ethyl ester, propyl ester, butyl ester,
-isobutyl ester, - / i-methoxy-ethyl ester,
- / i-ethoxy-ethyl ester, -methyl diglycol ester,
ethyl diglycol ester, methyl triglycol ester, 55

-ethyl-triglycol ester, - ^ - hydroxyethyl ester,
- / i-acetoxy-ethyl ester, - / <- (/ i'-hydroxy-ethoxy) -ethyl ester, -, hydroxy propyl ester,
-; - hydroxy-propyl ester, - «i-hydroxybutyl ester, -» i-hydroxy-hexyl ester, 60

5-Niiro-anthranilic acid methyl ester,
-isobutyl ester, -methyl diglycol ester,
-, i-methoxy-ethyl ester, - / V-butoxy-ethyl ester,
- / »- acetoxy-ethyl ester,

3- or 4-aminophthalic acidc-, 65 5-aminoisophthalic acid or amino

tcrephthalic acid dimethyl ester, di-ethyl ester,
-di-propyl ester, -di-butyl ester, 3- or 4-aminobenzoic acid amide, -methylamide, -propylamide, -butylamide, -isobutylamide, -cyclohexylamide, - // - ethyl-hexylamide, -y-methoxy-propylamide,

-y-ethoxy-propylamide,
2-, 3- or 4-aminobenzoic acid dimethylamk

diethylamide, pyrrolidide, morpholide, N-methyl-N-zi-hydroxy-ethylamide, 5-amino-isophthalic acid diamide, -bis-7-methox; propylamide,

Aminoterephthalic acid bis-diethylamide, 3- or 4-amino-phthalic acid imide, - / S-hydroxy-ethylamide, y-hydroxy-

propylamidj
3-Amino-6-nitro-phthalic acid - ^ - hydroxy-

ethylamide,
2-, 3- or 4-Aminobenzosulfonsäuredimethylamiü, -diethylamid, -pyrrolidid,

-morpholide,
Methylsulfuric acid-2'-, -3'- or -4'-amino-

phenyl ester,
Ethylsulfonic acid-2'-, -3'- or -4'-amino-

phenyl ester,
Butylsulfonic acid-2'-, -3'- or -4'-amino-

phenyl ester,
Benzenesulfonic acid-2'-, -3'- or -4'-amino-

phenyl ester,
2-amino-anthraquinone,

1-amino- ^ chloro-anthraquinone, 3- or 4-aminodiphenylene oxide, 2-amino-benzothiazole,
2-Amino-6-carbonic acid methyl ester benzothiazole.

2-amino-o-methyl-sulfonyl-benzothiazole, 2-amino-6-cyanobenzthiazole, 2-amino-6-nitro-benzothiazole, 5,6- or 6,7-dichloro-2-aminobenzothiazole, 4-amino -5-bromo-7-nitro-1,2-benzisothiazole, 3-amino-5-nitro-2,1-benzisothiazole, 3-amino-5-nitro-7-bromo-2,1-benzisothiazole, 2-amino -thiazoI,
2-amino-5-nitrothiazole,
2-Amino-4-methyl-thiazole-5-carboxylic acid ethyl ester,

2-Amino-4-methyl-5-acetyl-thiazole, 2-amino-3-cyano-4-methyl-thiophene

5-carboxylic acid ester,
2-phenyl-5-amino-1,3,4-thiadiazoI, 3-methylmercapto-5-amino-1,2,4-thiadiazole, 3- / ί-carbomethoxy-ethylmercapto-5-amino-1,2,4 -thiadiazoI.

Suitable diazo components of the aminoazoben zol series are, for example:

4-aminoazobenzene,

2 '^ -Dimethyl ^ aminoazobenzene, 3 ', 2-dimethyl-4-aminoazobenzene. 2,5-dimethyl-4-aminoazobenzene, 2-methyl-5-methoxy-4-amino; izobenzene, 2-methyl-4 ', 5-dimethoxy-4-aminoazobenzene, 4'-chloro-2-methyl-5-methoxy-4-aminoazobenzene, 4'-nitro-2-methyl-5-methoxy-4-aminoazobenzene 4'-Chloi-2-methyl-4-aminoazobenzene, 2,5-dimethoxy-4-aminoazobenzene, 4'-chloro-2,5-d! Methoxy-4-aminoazobenzene. 4'-nitro-2,5-dimethyl-4-aminoazobenzene, 4'-chloro-2,5-diinethyl-4-aminoazobenzene, 4'-Methoxy-2,5-dimethyl-4-aminoazobenzoL

4'-nitro-4-aminoazobenzene,

2,3'-dichloro-4-aminoazobenzene,
S-methoxy - ^ - aminoazobenzene.

As residues A are next to

CH ₃
- (CH ₂ J _n -CH-QH ₅

and hydrogen ζ. B. to mention: the alkyl radicals methyl, ethyl, propyl or butyl, the hydroxyalkyl radicals, / i-hydroxyethyl or -propyl, y-hydroxypropyl, (ii-Hydroxyhexyl, as well as the residues of the formulas

-CH ₁ -CH ₂ -O-CH ₂ -CH ₇ -OH

- (CH ₂ J ₃ -O- (CH ₂ J ₄ -OH

the alkoxyalkyl radicals ß-methoxyethyl, y-methoxypropyl, / i-ethoxyethyl, y-ethoxypropyl or the rest the formula

(CH ₂ J ₃ OC ₂ H ₄ OCH ₃
and the acyloxyalkyl radicals of the formulas

CH ₂ -CH ₂ -O-acyl
(CH ₂ J ₃ - O-acyl
CH ₂ -CH-O-acyl

CH ₃

(CH ₂ ) ₆ -O-acyl
(CH ₂ J ₂ - O - (CH ₂ J ₂ - O-acyl

Mono-, di- or trichlorobenzene, tetrahydrofuran, dioxane, dimethylformamide, N-methylpyrrolidone or pyridine can be added.

In the case of esterification with free acids it can of Be advantageous inorganic or organic catalysts, e.g. B. HCl gas or p-toluenesulfonic acid to be added and to allow the water formed to escape from the reaction mixture by evaporation. If acid anhydrides or chlorides are used for esterification, then in In special cases, the relevant acids can also be used. So the implementation can be done with Perform acetic anhydride in glacial acetic acid. When using acid chlorides as esterifying agents it is advantageous to add acid-binding agents to the reaction mixture, e.g. B. sodium carbonate or acetate, magnesium oxide or pyridine. As an esterifying agent are specifically mentioned, for example: formic acid, acetic acid, chloroacetic acid and the esters, anhydrides or chlorides of these acids, furthermore ethyl chloroformate or diketene.

Dyes and dye mixtures of the general formula 1 a are particularly useful from a technical point of view

CN (la)

NH-A ¹

A ¹ -HN

(CH ₂ J ₃ - O - (CH ₂ J ₄ - O-acyl

where acyl is for example

CO-H CO-CH ₃ CO-CH ₂ Cl
CO-CH ₂ -CO-CH ₃ CO-CH = CH ₂

In the preparation of the dyes of the general formula I, the amines are diazotized as common. The coupling is also carried out as usual in an aqueous medium, optionally with the addition of Solvents, carried out with weak to strongly acidic reaction.

The preparation of the coupling components of the general formula III is in principle in German Offenlegungsschrift 2062 717, the information there applies accordingly here.

If the dyes of the formula I according to the invention contain an ester group in the radical A, the compounds of the formula I can in principle be prepared by the process indicated if the corresponding ester group is already contained in the coupling component. In some cases, however, it is also expedient to introduce the acid residue (acyl) into the finished dye of formula 1. The free acids, their anhydrides, are suitable for this. Chlorides or esters, in which case it is expedient to use inert diluents, or solvents, as in Y nitro, cyano, chlorine, bromine, carbomethoxy, carboethoxy, / I-methoxycarbethoxy, methylsulphonyl, ethylsulphonyl, methyl, methoxy, phenylazo, Y ¹ hydrogen, nitro , Chlorine, bromine, cyano, methyl, methoxy, carbomethoxy, carboethoxy, methylsulfonyl or ethylsulfonyl and Y ² hydrogen, chlorine, bromine, cyano. Methyl, methoxy, carbomethoxy or carboethoxy.

40 an A ¹ - (CH ₂ J _n -CH-QH ₅
CH ₃

and the other ω-hydroxyhexyl, / I-hydroxyethyl, 0-hydroxypropyl, γ-hydroxypropyl or a residue of the formulas

- (CH ₂ J ₂ -O- (CH ₂ J ₂ OH
(CH ₂ J ₃ O (CH ₂ J ₄ OH
C ₂ H ₄ OCH ₃ C ₃ H ₆ OCH ₃
CH ₂ CH ₂ OCHO
CH ₂ CH ₂ CH ₂ OCHO

CH ₂ -CH ₂ OCOCH ₃

CH ₂ CH ₂ OCH ₂ Ch ₂ OCHO

are.

In the case of dyes with ester groups, those with 1 to 4 carbon atoms in the acyl radical are preferred.

Furthermore, the corresponding dyes given as diazo components are particularly valuable if by nitro, chlorine, bromine, cyano, methyl, methyl mercapto,, (- Carbomcthoxy-ethylmercapto,, .'-Carba

ethoxy-ethylmercapto, carbomethoxy, carboethoxy or acetyl-substituted benzothiazole, benzisothiazole, Contain thiazole, thiadiazole or thiophene.

Some of the particularly valuable diazo components are: 5

4-nitro-aniline,

2-chloro-4-nitro-aniline,

2-bromo-4-nitro-aniIine,

2-cyano-4-nitro-aniline, | ₀

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-15

/ i-methoxy-ethylamide,
2-amino-benzonitrile,
3-chloro-4-aminobenzonitrile,
2-chloro-5-aminobenzonitrile,
2-amino-5-chlorobenzonitrile, 20

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, 25

2-Amino-3-bromo-5-nitro-benzonitrile, 2,6-dicyano-4-nitro-aniline,
2,5-dichloro-4-nitroaniline,
2,6-dichloro-4-nitro-aniline,

2,6-dibromo-4-nitro-aniline, 30

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

2-amino-3,5-dinitro-benzonitrile, 35

l-amino-4-nitrobenzene-2-methylsulphone, l-amino-4-nitrobenzene-2-ethylsulphone, 4-methylsulphonyl-aniline,
1-amino-2-chlorobenzene-4-methylsulfone, 1-amino-2,6-dibromobenzene-4-methylsulfone, 40

l-amino-2,6-dichlorobenzene-4-methylsulfone, 2- and 4-amino-benzoic acid ester, 2-Amino-5-nitro-benzoic acid ester, 2-Ammo-3-chloro-5-nitro-benzoic acid ester, 2-Amino-3,5-dichloro-benzoic acid ester, 45

2-Amino-3,5-dibromo-benzoic acid ester, 2-amino-3,5-dinitro-benzoic acid-methyl ester

or - / i-methoxy-ethyl ester,
2-amino-terephthalic acid diethyl ester, 4-amino-azobenzene,
2.3 '-Dimethyl-4-amino-azobenzene, 2,3-dimethyl-4-amino-azobenzene. 2,5-dimethyl-4-amino-azobenzene, 3,5-dibromo-4-amino-azobenzoL

Of the particularly valuable heterocyclic diazo components are mentioned:

55

2-amino-5-nitro-thiazole,

2-amino-4-methyl-5-nitro-thiazole.

2-Amino-4-methyl-thiazole-5-carboxylic acid ethyl ester,

2-Amino-5-phenyI-1,3,4-thiadiazole, 3-phenyl-5-amino-1,2,4-thiadiazole, 3-methyl-meΓcapto-5-amiπo-1, 2,4-thiadii ' rol, 3- _/ ί-carbonnethoxy-ethyltnercapto-5-amino-

1,2,4-thiadiazot, S - ^ - Carboethoxy-ethylmercapto-S-amino- 1.2.4-thiadia7ol.

2-amino-6-cyano-benzothiazole,
2-amino-6-carboxylic acid methyl-ester-benzthiazole, 2-amino-6-nitro-benzthiazole,
2-amino-3-cyano-4-methyl-thiophene-5-carbon

ester,

3-Amino-5-nitro-2, l-benzisothiazole,
S-Amino-S-nitro ^ -chlor ^ l-benzisothiazole,
3-Amino-5-nitro-7-bromo-2, l-benzisothiazole,
4-Amino-7-nitro-1,2-benzisothiazole,
4-AmitiiO-5-bromo-1,2-benzisothiazole,
4-amine oS-bromo ^ -nitro-1,2-benzisothiazole,
4-amine oS-cyano ^ -nitro-1,2-benzisothiazole,
4-Amino-5-chloro-7-nitro-1,2-benzisothiazole.

The new dyes are yellow to blue and are suitable for dyeing textile materials Acrylonitrile polymers, synthetic polyamides, cellulose esters such as 2V2 or triacetate, and in particular of synthetic linear polyesters such as polyethylene glycol trephthalate or chemically similarly structured polymers. Strong dyeings are obtained which are distinguished by excellent fastness properties distinguish.

The data on parts and percentages in the following examples are based on weight, unless otherwise noted.

example 1

A mixture of 187 parts of 2,6-dichloro-3-cyano-4-methyl-pyridine, 200 parts of isopropanol and 300 parts of 2-phenylpropylamine are stirred at about 4.5 to 55 ° C. for 8 hours. Then one lets cool and pour the mixture into about 1500 parts of water and 200 parts of concentrated hydrochloric acid with stirring and 200 parts of ice. The mixture is stirred for a further 1 hour, and the precipitate that has formed is sucked off the probable one formula

CH ₃
NH-CH ₂ -CH

and washes it neutral with water. After drying, about 240 parts of a colorless powder which ^{melts at 100 to 105 °} C. are obtained.

15 parts of this powder are stirred with 40 parts / f Hydroxyäthyb ~ nin 6 hours at 145 to 16O ⁰ C. The mixture is then allowed to cool, 100 parts of v / ater are added to the mixture and the mixture is acidified to a pH of about 0 to 1 with hydrochloric acid. A solution of the coupling component of the probable formula is obtained - optionally with the addition of a little glacial acetic acid or dimethylformamide

H, C

CN

NH-CH ₂ -CH

-N

NH - CH ₂ - CH ₂ - OH

The solution (or suspension) of this coupling component is by adding ice to 0 bis

509 619/213

SMtQ

(θ

C cooled and mixed with a diazonium salt solution, which is obtained as follows:

6.9 parts of p-nitroaniline are mixed with approximately 30 parts concentrated hydrochloric acid (30%) and 80 parts of water are added, then the mixture is turned to OC cooled and mixed with 15 parts by volume of 23% sodium nitrite solution. The mixture is stirred for 2 hours after, eliminates any excess of nitrous acid present as usual and filtered.

10

The filtrate is added to the coupling mixture,

and so much sodium acetate or sodium hydroxide solution is then gradually added, with stirring, that the pH of the coupling mixture is about 2 to 3. If the mixture becomes difficult to stir, ice water can be added. After the coupling has ended, the mixture is ^{heated to 70 to 80 °} C., filtered, washed with water and dried. About 20 parts of a brown powder are obtained

ίο probable formula

which dissolves in orange dimethylformamide and polyethylene terephthalic fabric in strong, clear orange Dyes shades with excellent fastness properties.

Analogously to the procedure described, the following can be carried out using diazo and coupling components characterized dyes are obtained.

Tabel

Coupling component:

H ₃ C CN

example

<^ ■ / - NH - CH ₂ - ! Jtii / i'kiimpoiicnlt: /, - '■■ · CN H -CH ₂ CH- -QH S. OH yellow NHR ₂ / /-NO Br -f NH, -CH ₂ -CH ₂ CH ₃ yellow -CH ₂ -CH R. yellow COOCH, -CH ₂ I. yellow CH, - OH - CH, -CH ₂ - OH - CII, -CH ₂ -OH yellow CN - CH ₂ OH yellow <_; v-nh ₂ H -CH ₂ yellow -CH ₂ -CH ₂ O - CH ₂ - CH ₂ - yellow - CH ₂ -CH-
I. - O ■ - CH *, yellow -CH; CH, yellow CH ₂ - OH CN -CH ₂ -CH ₂ - OH OH yellow c \ - <f V-NH ₂ -H -CH, -OH yellow ^x --- CH ₂ CH ₂ yellow - CH ₂ CH ₂ O CH ₁ - CH ₂ - yellow CH. CH ₁ yellow -CH ₂ OH CH, -CH ₂ - OH OH yellow H CH ₂ OH tanned CH ₂ CH ₂ yellow CH, CH
i O CH ₂ CH ₂ - yellow ch " ₂ CH. yellow CH ₂ OH CH, CH ₂ OH yellow -OH ο CH ₂ - CH ₂

I iirbion

& - ■

ftfiQ

Example no

23 24 25 26

11th

IJia / iikomponciilc

Br- <^> NII ₂ Br

COOCH, Cl / V Nile, Cl

O, T «

CI

O ₇ N -

NH,

O ₂ N - <(> -NH,

OCII,

- NH,

NO ₂ NH ₂

continuation

12th

CN

R,

-CH ₂ -CH ₂ -OH

- CH ₂ -CH ₂ - CH ₂ - OH

-CH ₂ -CH-OH

CH ₃ -CH ₂ -CH ₂ -O-CH ₂ -CH ₂ OH

CH ₂ -CH ₂ -OH

- CH ₂ - CH ₂ - CH ₂ - OH -CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -OH

H -CH ₂ -CH ₂ -OH

- CH ₂ - CH ₂ - CH ₂ - OCOCH ₃

OH

- CH ₂ CH

CH ₃

-CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -OH -CH ₂ -CH ₂ -O-CH ₃ -CH ₂ -CH ₂ -CH ₂ -O-CH ₃ -CH ₂ -CH ₂ OCHO - ( CHA-OH

- H

-CH ₂ -CH ₂ -OH

- CH ₂ -CH ₂ -CH ₂ -OH -CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -OH

OH / -CH ₂ -CH

CH ₃

-CH ₂ -CH ₂ -CH ₂ -O-CH ₃ -CH ₂ -CH ₂ -CH ₂ OCOCH ₃

-CH ₂ -CH ₂ -OH

- CH ₂ - CH ₂ -CH ₂ - OH -CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -OH

-CH ₂ -CH ₂ -OH

-CH ₂ -CH ₂ -CH ₂ -OH

-CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -OH

-CH ₂ -CH ₂ -OH CH ₂ -CH ₂ -CH ₂ -OH

CH ₂ - CH ₂ OH

CH ₂ CH ₂ CH ₂ OH

CH ₂ -CH ₂ O-CH ₂ -CH ₂ -OH

CHj CH, OH CH ₂ -CH ₁ CH ₂ - OH CHj-CH ₂ - Q-CH ₂ -CH ₂ -OH

I iirblon

orange orange orange orange

orange

orange orange orange orange

orange orange orange

orange

orange orange orange orange orange

Scarlet fever scarlet fever scarlet fever

Scarlet fever

scarlet fever

scarlet scarlet scarlet

geibstichigrol yellow-tinged red geibstichigrol

orange orange

yellow yellow yellow

orange orange orange

ftfiQ

example

13th

Diazokomrtonenlc

COOC ₂ H,

NH ₂

COOC ₂ H ₅

SO ₁ CH,

Cl

Cl-

l- / V-

CK,

-NH ₂

Br-

COOCH, V-NH ₁

Br

H

I Il

CH, -N-S O

V-

Br

NH,

O λ

C ₃ H ₅ -OC-Z) -NH,

CH, -CH, - Ο -CH,

I *

CH,

O =

/ ^N \

NH,

CH- O CH ₂ CH ₃ NC

! Il

H

C ₄ H,

NH ₂

continuation

14th

CH ₂ CH ₂ -CH ₂ -OH
CH ₂ -CH ₂ -O-CH ₂ -CH ₁ -OH

-CH ₂ -CH ₂ -OH

-CH ₂ -CH ₂ -CH ₂ -OH

- CH ₂ - CH ₂ - CH ₂ - O - CH,

-CH ₂ -CH ₂ OH

- CH ₂ - CH ₂ - CH ₂ - OH

- CH ₂ - CH ₂ - O - CH ₂ - CH ₂ - OH

-CH ₂ -CH ₂ -OH
-CH ₂ -CH ₂ -CH ₂ - OH
-CH ₂ -CH ₂ -O-CHj-CH ₂ -OH
-CH ₂ -CH ₂ - O -CH,

-CH ₂ -CH ₂ - CH ₂ - OH
-CH ₂ -CH, -OH

-CH ₂ -CH ₂ -CH ₂ -OH
-CH ₂ -CH ₂ 0-CH ₂ -CH ₂ -OH

CH ₂ -CH ₂ -OH
-CH ₂ -CH ₂ -CH ₂ -OH
-CH ₂ -CH ₂ - Ο - CH, - CH, - OH

CH ₂ -CH ₂ -OH
CH ₂ - CH ₂ - CH _:. - OH
OH

-CH ₂ -CH

CH ₃

NH ₂

-CH ₂ -CH, - Ο - CH, - CH ₂ - OH

-CH ₂ -CH ₂ OH -CHj-CH, -CH ₂ -OH

-CH ₂ - CH ₂ - O - CH ₂ -CH ₂ - OH

-CH ₂ CH ₂ OH -CH ₂ -CH ₂ CH ₂ -OH

-CH ₂ CH ₂ OH -CH ₂ CH ₂ CH ₂ OH

Cure

yellow yellow yellow

yellow yellow yellow yellow

yellow yellow yellow

yellow yellow yellow yellow yellow

yellowish color yellowish color color

orange orange

yellow yellow yellow

golden yellow golden yellow

golden yellow golden yellow

yellow yellow yellow

yellow yellow

yellow yellow

869

15th

Coupling component:

Table 2

H ₃ C CN

NH - CH ₂ - CH - QH

• 6 "5

CH,

16

Example no.

95 96 97

98

100

101 102 103

109 ilO

111 112

113 114 115

DiaA> components

COOCH,

<( Vnh,

CN

<? V-NH,

CH ₂ -CH ₂ -OH
CH ₂ -CH ₂ -CH, - OH
H

Cl

C).

NH,

CT,

Cl-

NH,

CH ₂ -CH ₂ -OH
CH ₂ -CHj-CH ₂ -OH
-CH ₂ -CH ₂ -CH ₂ -O- (CH ₂ J ₂ OH

CH ₂ -CH ₂ -OH
CH ₂ -CH ₂ -CH ₂ -OH
- CH ₂ -CH ₂ -O - CH ₂ - CH ₂ - OH

CH ₂ -CH, OH

CH ₂ - CH ₂ -CH ₂ -OH

CH ₂ -CH ₂ -O- (CH ₂ I ₂ OH

CH ₂ -CH ₂ -CH ₂ -OH
CH ₂ -CH ₂ -O-CH ₂ -CH ₂

CH ₂ -CH ₂ -OH
CH ₂ -CH ₂ -CH ₂ -OH

OH

"CH2 CH2 OH2 OH
CH ₂ -CH ₂ - O - (CH ₂ I ₂ OH

CH, CH, Oll -CH ₂ -CH ₂ - OH OH N - ■■ - () -CH ₂ -CH ₂ - CH ₂ - CH., - ~ CH ₂ CH, CH ₂ NII.

Color ion

yellow yellow yellow

yellow yellow yellow

yellow

golden yellow

yellow

orange orange orange

orange orange

Scarlet fever

yellow yellow

yellow yellow yellow

^L ' ^s P' ^c

given, and the mixture is then set to O to ^ 65 cooled. 19.5 parts of 3-amino-5-nitro-2,1-benzisolhia / ol 32.5 parts of 23% strength nitrosylsulfuric acid are then added dropwise at this temperature. the / Ground while stirring at 15 to 25 C in portions azo is after about 3 to 4 hours u about 75 to 5 parts% sulfuric acid at 0 to 5 ° C ended. Now you give the Dk

17 18

nium salt mixture to a solution or suspension, cooled to O "C, of 34 parts of the coupling components jier.te of the formula

CN

NH - CH, - CH - C ₆ H,

NH-CH ₂ -CH ₂ -CH ₂ -O-CH ₃

in 50 parts of 30% hydrochloric acid, 500 parts of water that the temperature of the coupling ^ -uusche; and 150 parts of glacial acetic acid. During the coupling does not exceed 5 ° C and the pH value finally gradually add ice and sodium acetate to about 2. The unusual dye of the formula

H ₃ C

N = N

/ - X

CN

CH ₃
NH - CH ₂ - CH - C ₆ H ₅

NH - CH ₂ - CH ₂ - CH ₂ - O - CH ₃

is filtered off, washed with hot water and dried. About 53 parts of a black powder are obtained which dissolves in dimethylformamide with a reddish blue color.

Example 117

50 parts of the powder obtained in Example 116 are mixed with about 200 parts of 85-95% strength sulfuric acid Stirred for 5 hours at 80 to 100 ° C. The mixture is then poured into 1500 parts of ice water and the precipitated product is filtered off Dye of the formula

H ₃ C CONH _{2 r} "

N = N - <^> - NH - CH ₂ - CH - QH ₅

/ ~ ^N
NH - CH ₂ - CH ₂ - CH ₂ - O - CH ₃

off, wash with water and dry. About 40 parts of a dark powder are obtained, which is in dimethylformamide dissolves with blue paint and dyes polyethylene terephthalate fabric in blue tones.

Coupling component:

Table 3

NH-CH ₂ -CH-C ₆ H ₅

CH ₃

I Jl.l / iiklM

(KN

CN

.- NH,

K-

CH ₂ CH ₂ -OH
CH ₂ - CH ₂ -CH, OH
CH ₂ CII OH

CH,

CW; O] ₁ O -CII, CH
-CH, CH, CH, OCHO
Il

■ (CH ₂ ) ,, OH
-CH ₂ -CH, O COCII,

OH

l-arbinn

yellowish red yellowish red

yellowish green yellowish red scarlet fever
balanced gclbstichigrol

eispicl No.

19th

Diazo component

continuation

20th

Br

O, N

NH,

CN

/ -NH, Br

CN

O ₂ N- / "V-NH,

Cl

COOCH,

O ₂ N - <f / NH,

COOCH,

O ₂ N- / V-NH ₂ Br

O ₃ N - /) NH,

C " 0OCH ₂ -CH, OCH, NO, O ₂ N ■ - / V-NH, Cl O ₂ N / V-NH ₂ Cl Br Ο, Ν ■ / / Nile, Mr (Ί

Ο, Ν

NH, R,

-CH ₂ -CH ₂ -OH

- CH ₂ - CH ₂ - CH ₂ - OH

-CH ₂ -CH-OH

CH ₃

-CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -OH
H

-H
-CH ₂ -CH ₂ -OH

- CH ₂ - CH ₂ - CH ₂ - OH
CH ₂ -CH-OH

CH ₃

-CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -OH
CH ₂ -CH ₂ -O-CH ₃
CH ₂ -CH ₂ -CH ₂ -O-CH ₃

- CH ₂ - CH ₂ - O - COCH ₃

- CHj C-H2 OH

- CH ₂ - CH ₂ - CH ₂ - OH
CH ₂ -CH-OH

CH ₃

-CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -OH
CH ₂ -CH ₂ -O-CH ₃

C ₂ H ₅

-CH ₂ -CH ₂ -OH

- CH ₂ - CH ₂ - CH ₂ - OH

- CH ₂ - CH ₂ - O - CH ₂ --CH ₂ -

OH

-CH ₂ -CH ₂ -OH
-CH ₂ -CH ₂ -CH ₂ -OH
-CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -OH

CH ₂ -CH ₂ -OH
CH ₂ -CH ₂ -CH ₂ -OH

CH ₂ -CH ₂ -OH
CH ₂ -CH ₂ -CH ₂ -OH
CH ₂ -CH ₂ -O -CH ₂ -CH ₂ -OH
CH, -CH ₂ -O -CH,

CH ₂ -CH ₂ - OH -OH CH, -CH ₂ - CH ₂ CH ₂ -CH ₂ -OH CH, -CH ₂ - O - COCHj CH, -CH ₂ - O CH, -CH ₂ - OH OH CH, CH, CH, CH, CH -
ι OH I.
cn, CH, CH-OH (II, cn. O

Carbion

scbarlach scarlet fever scarlet fever

Scarlet fever

ruby ruby ruby ruby

ruby ruby ruby ruby

ruby ruby ruby Ruhin

ruby ruby ruby

Red
Red
Red

Red
Red
Red

Red Red

Red
Red
Red
Red
Red

CII, VW ₂ OH

CII, CH ₂ CM ₂ OH

CH, CH, CII ₂ O Cl

Hi brownish scarlet fever

brownish scarlet

braunstichii scarlet

Bet game I No.

170 171 17? 173

174 175

176 177 178

179 180 181

182 183 184

185 186 187 188

189

190 191 192

193 194 195 196

197

21

Diazo component

continuation

22nd

CN

O, ti - / ^ -NH, CN

SO ₂ NtC ₂ H ₅ ),

NO,

NC — f V-NH,

Cl

Cl

C ₄ H ₁ InINHCO-C> NH,

/ Cl '

Br

(n; C ₄ H.NH -QO - / V-NH ₂ Br

SO ₂ CH,

O ₂ N

NH ₂

O ₂ N

O ₂ N

NH,

Λ A

Ί ^N

Br (Cl)

O NII,

Nile,

. R,

-CH ₂ -CH ₂ -OH

- CH ₂ -CH ₂ -CH ₂ -OH

- CH ₂ - CH ₂ - O - CH ₂ - CH ₂ - OH

- CH-) - CH2 CHi O CH3

-CH ₂ -CH ₂ -OH

CH ₂ -CH ₂ -OH
- CH ₂ - CH, - CH ₂ - OH
-CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -OH

CH ₂ -CH ₂ -OH
CH ₂ -CH ₂ -CH ₂ -OH
CH ₂ -CH ₂ -O -CH ₂ -CH ₂ -OH

CH ₂ -CH ₂ -OH
-CH ₂ -CH ₂ -CK ₂ -OH
CH ₂ - CH ₂ - O - CH ₂ - CH ₂ - OH

-CH ₂ -CH ₂ -CH ₂ -OH

-CH ₂ -CH-OH

CH ₃
- (CH ₂ J ₃ - Q- (CH ₂ I ₄ -OH

CH ₂ -CH ₂ -CH ₂ -OH
CH ₂ -CH -OH

CH ₃
-CH ₂ -CH ₂ - O - CH ₂ - CH ₂ - OH

(CHA-OH
- (CH ₂ I ₃ -O- (CH ₂ I ₄ -OH

CH ₂ -CH ₂ -CH ₂ -OC-CH ₃

CH ₂ -CH ₁ - O CH ₂ -CH ₂ - OH

CH ₂ -CH ₂ -CH ₂ -OH

CH. CH ₂ O-CH ₂ -CH ₂ ■■ OH

CII ₂ CH, CH ₂ Oll

(H, CH, O CH, CIl, OH

hue

blaustichij.ru bluish green bluish green bluish green

red red

red red red

yellow yellow yellow

yellow yellow yellow

red red red red

Red

reddish blue reddish blue reddish blue

reddish blue reddish blue reddish blue reddish blue

blue (blue)

yellow-brown yellow-brown

yellow gclh

example

202 203

204 205 206 207

208 209 210

23

--- ■ I!

'> · - S ■■■>? / ■ · Nil, ,, / | j W

NO;

Ο, Ν - ^ / Nile,

Cl

NO, O, N <f / NH,

Br

Ο, Ν

/ Nile,

CH ₁ OC

NC - ^:

NH,

continuation

24

(), N S. N I. N NH, ( Ο, Ν S. N Br NH, N Ο, Ν S. ί NHj N O ₂ N S. NH, / SCWjH,
NII,

R,

- CH ₂ - CH ₂ - O - CH ₂ - · ■ CH ₂ - OH
(CHj) ₃ -OH

- CH ₂ -CH ₂ -OH
-CH ₂ -CH ₂ -CH ₂ -OH
H

- CH ₂ -CH ₂ - 0 - CH ₂ -CH ₂ - OH

- (CH ₂ I ₃ -OH

- CH ₂ - CH ₂ - O - CH ₂ --CH ₂ - OH

-CH ₂ -CH ₂ -OH

-CH ₂ -CH ₂ -CH ₂ -OH
-CH ₂ -CH ₂ -OH

-CH, - CH, - OH

-CH ₂ --CH ₂ --OH

-CH ₂ -CH ₂ -CH ₂ -OH

CH ₂ -CH ₂ -Ο -CH ₂ -CH ₂ -OH
- (CHj) of ₃ - 0 - (CH _{2) a} - OH

-CH ₂ -CH ₂ -CH ₂ -OH
--CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -OH

CH ₂ CH ₂ CH ₂ - OH

CH, CH ₂ C) CH ₂ -CH ₂ -OH

CH ₂ CH ₂ - CH ₂ - OH

CH ₂ CH ₂ Ο - CH ₂ -CH ₂ -OH

CH ₂ CH, CH ₂ OH

! • 'arhlon

yellow
yellow

bUiustichigrot bluustichigrot bliiustichigrol bluestichigrot

bluish red bluish red bluish red

Scarlet fever

Scarlet fever

Scarlet fever

bluish tint Waustichigrol hlaustichigrot bluish red bluish red

violet
violet
bluish red

violet violet

violet violet

robin

example

25th

Diazo component

continuation

26th

CH, - S - if N

, Nile,

CH, O-C-C, H ₄ -S- -τ. N

'} - Nile,

CH., - _{T |} - -N

H, -τ. N

, N Λ ) L._ _ΝΗι

CH,

CH, -OC-O

CH,

C, H ₅ O -C-

I! O

CN NH,

- CN

Nile,

NO,

Cl / ·· ■■ ^N ":

CN NO,

O, N

CH,

O, N ■ -

C ,, H ₅

■ NH,

CN

-CN

, '·' - ■■ NH,

NC

C-C S NH, NC H

R,

- H

CH ₂ -CH ₂ -OH
CH ₂ - CH ₂ -CH ₂ - OH
- CH ₂ - CH ₂ - O - CH ₂ - CH ₂ - OH

-CH ₂ -CH ₂ -OH
-CH ₂ -CH ₂ -CH ₂ -OH
CH ₂ - CH - OH

CH,

-CH ₂ - CH ₂ - O - CH ₂ - CH ₂ - OH
H

-CH ₂ -CH ₂ -OH
-CH ₂ -CH ₂ -CH ₂ -OH
CH ₂ - CH ₂ - O - CH ₂ - CH ₂ - OH

CH ₂ -CH ₂ -OH
-CH ₂ -CH ₂ -CH ₂ - OH
-CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -OH

Cl

CH,

-CH ₂ - CH ₂ OH
CH ₂ -CH ₂ -CH ₂ - OH
CH ₂ - CH ₂ - O - CH, - CH ₂ - OH

-CH ₂ -CH ₂ -CH ₂ -OH

-CH ₂ -CH ₂ -OH

- CH ₂ - CH ₂ --CH ₂ - OH

-CH ₂ -CH ₂ -OH

- CH ₂ - CH ₂ - CH ₂ - OH

-CH ₂ CH ₂ -CH ₂ OH

larhlon

orange orange orange orange

orange orange orange

orange orange

violell vide »violet

bluish red bluish color bluish red bluish red

bluish tint blue bluish tint blue bluish tinge red

bluish-tinged red bluish-tinged red, bluish-tinged red

violet violet

reddish blue

Coupling component:

ftfiQ

continuation

example
No. Diazo component Ur / ■ ' CN Br
/ -CH ₂ -CH κ, _? -ΟΗ OH ₂ - 0 - CH ₂ --CH ₂ - OH l-'arbliin 254 / y · ■. Mil -CH ₂ -CH ₂ -CH ₂ -OH Scarlet fever 255 \ / ' ^> - Η y ~~ O ~~~ CH2 CH2 Scarlet fever 256 O ₂ N N v_ rip V_- ΓΙ OH Scarlet fever 257 V ~ yNH ₂ -CH ₂ -CH ₂ - OH Scarlet fever 258 SO ₂ CH, Λ / -CH ₂ -CH _: , —Ο —COCH ₃ OH yellowish red 259 <L> ^NHi N -CH ₂ -CH \ - CH ₂ -OH ₂ --CH ₂ -CH ₂ OCHO yellowish red 260 O Ν -CH ₂ -CH ι O CH ₂ CH ₂ yellowish red 261 Ui IN CN - (CH-) _h OH ₂ —CH ₂ —OH yellowish red 262 -CH ₂ -CH 2 OH OH yellowish red 263 Ό " ^NII: -CH ₂ -CH yellowish red 264 Mr LI ₂ -OH Red 265 O ₂ N -CH ₂ -CH ₂ - CH ₂ - OH Red 266 CN -CH ₂ -CH -OH OH Red 267 -CH ₂ -CH
ι .1 ruby 268 f, - Nl I ₂ I.
CH ₂ —Ο —CH ₂ -CH ₂ - ruby 269 O ₂ N Cl -CH ₂ -CH ₂ -OH OH ruby NO ₂ -CH ₂ -CH , -CH ₂ -OH 270 { , - NH ₂ -CH ₂ -CH , - Ο - CH ₂ -CH ₂ - ruby 271 SO ₂ CH, -CH ₂ -CH ) - (CH ₂ I ₄ -OH Red 272 <f> ~ NH ₂ - (CH ₂ I ₃ -C ruby 273 O ₂ N S '"} /
\ ■ ''' , -CH ₂ -OH ruby 274 N -CH ₂ -CH ruby , -CH ₂ -OH 275 O ₂ N -CH ₂ -CH , —Ο —CH ₂ -CH, - violet -CH ₂ -CH 276 O ₂ N - ruby 277 ₂ -CH ₂ -OH ruby -CH ₂ -CH -CH ₁ -CH ₂ -O-CH ₂ -CH ₂ - 278 O ₂ N - violet 279 - CH ₂ - CH ₂ - CH ₂ - OH violet -CH ₂ -CH 280 O ₂ N γ reddish blue 281 I. reddish blue

ftfiQ

Example no.

29

continuation

30th

Diazo component

O ₃ N - ~ r V - - | - NII ₂ S

Cl

NO ₂ O ₂ N - / V- NU,

NO ₂

O ₂ N - ^ C'y ~ NH ₂

\ Cl

NO ₂

O ₂ N / V NH ₂

CN

COOCH,

O ₂ N <( V NH ₂

Coupling component: U ₁

-CH ₇ CH, ■ - () -CH, -CH, -OH

H
-CH ₂ -CH ₂ -OH

CH2 C-H2 CH2 OH

CH2 OH2 O OH2 CH2 OH

CH2 CH2 CH2 OH

C H 2 OH 2 O CH 2 GH 2 OH

- · CH ₂ - CH ₂ - CH ₂ - OH
-CH ₂ -CH ₂ -O- (CH ₂ J ₂ OH

CH2 CHj CH2 OH

CH 2 Cv H 2 O C> H 2 C> H 2 O H

Table 5

H ₃ C CONH ₂

NH-CH ₂ -CH-Q ₁ H ₅
NH - R ₂ ^{CH 3}

l-arhlon

blue

Red
Red
Red
Red

bluish red bluish red

bluish red bluish tinted red

Red
Red

example

297 298 299 300 301 302

303 304 305 306 307 308

Diazo component

O ₂ N

Cl

CN

/ O ₂ N <S NH ₂

CN

NHj

Br R,

CH ₂ - CH ₂ - O - COCH ₃
CH ₂ - CH ₂ - CH ₂ - O - COCH ₃
CH ₂ -CH ₂ -CH ₂ -OH
CH ₂ -CH ₂ -O-CH ₃

CH ₂ -CH ₂ -OCOCH ₃

CH ₂ - CH ₂ - CH ₂ - OCOCH ₃

CH ₂ CH ₂ -CH ₂ OH

CH ₂ -CH ₂ -O-CH ₂ -Ch ₂ -OCOCH ₃ CH ₂ - CH ₂ -O - CH ₂ -CH ₂ - OH

CH ₂ -CH ₂ -O-CH ₃

CH ₂ -CH ₂ -CH ₂ OCOCH ₃

CH ₂ -CH ₂ -CH ₂ -OH

CH ₂ -CH ₂ -O-CH ₂ -Ch ₂ -OCOCH ₃ CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -OH

CH ₂ -CH,

CH ₂ - CH ₂ - CH ₂ O - CH ₃

I'arhion

Red
Red
Red
Red

bluish gray bluish green bluish green bluish gray bluish green bluish green

red-violet red-violet red-violet red-violet red-violet red-violet

869

31

continuation

example
No. Diazo component R, hue blue
blue
blue
blue
blue
blue
blue
blue
blue 309
330
311
312
313
314
315
316
317 ^S N -CH ₂ -CH ₂ -O-COCH ₂ -COCh ₃
- CH ₂ - CH ₂ - OCOCH ₃
- CH ₂ - CH ₂ - CH ₂ - O - COCH ₃
- CH ₂ --CH _{2 - CH 2} - OH
-CH ₂ -CH ₂ -O-CH ₃
-CH ₂ -CH ₂ -CH ₂ -OC ₂ H ₅
-CH ₂ -CH ₂ -O-Ch ₂ -CH ₂ -OCHO
-CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -OH
- CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -O-COCh ₃ greenish blue 318 O, N - / \ r- NH,
I j S
IN
Br - CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -O-COCh ₃

Table 6

Coupling component:

H ₃ C CN

CH ₃

NH - CH ₂ - CH ₂ - CH - C ₆ H ₅

NH-R ₂

example
No. Diazo component H H H H -CH ₂ R, -OH Color ion 319 -CH ₂ -CH ₃ -CH ₂ -CH ₂ - CH ₂ - CH ₂ - OH Scarlet fever 320 - CH ₂ -CH ₂ "CH2 -CH _; OH fire red 321 CH2 \ _- rl2 -CH Red CN -CH ₂ CH ₃ 322 O ₂ N - ^ ~ \ ~ ^Ν " ² -CH ₂ - O - CH ₂ -CH ₂ -OH yellowish red CVi
L-Hj 323 -CH, - OH yellowish red 324 -CH ₂ / "" ¹ U OU
V_, ri2 VJrI Scarlet fever 325 -CH ₂ - O - CH ₂ -CH ₂ -OH Scarlet fever 326 O ₂ N - <f \ - NH ₂ Scarlet fever 327 - CHj - OH Scarlet fever 328 -CH ₂ -CH ₂ -OH orange 329 O ₁ N- <f \ -IsJH ₁ -CH ₂ - 0 -CH ₂ -CH ₂ -OH orange 330 orange 331 CH ₂ -OH orange 332 CN -CH ₂ -CH ₂ -OH bluish red 333 O ₂ N - / "V-NII ₂ ruby 334 Cl ruby

continuation

example
No. Diazo component Rj hue Red
Red
Red 335
336
337 NO,
Ο, Ν —ζ ') - NH, H
-CH ₂ -CH ₂ -OH
-CH ₂ -CH, -CH, -OH yellow
yellow 338
339 CN
/
<^ NH ₂ H
-CH ₂ -CH ₂ -OH

The other diazo components of Examples 1 to 318 result with the coupling components according to of the formula above Table 6 dyes that differ from the corresponding dyes with the 2-phenylpropylamine radical differ only slightly in their properties.

Claims (1)

Patent claims: 1. Azo dyes with 2,6-diaminopyridines as coupling components, characterized by the general formula CH ₁ D-N = N