DE2226933B2 - Azo dyes with 2,6-diaminopyridines as coupling components, process for their preparation and their use - Google Patents

Description

A-HN

NH-A

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

CH ₃
(CHACH-C ₆ H ₅

where η is 1 or 2, and the other radical A 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 are substituted alkyl with 1 to 6 carbon atoms, where the acyl groups have 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

Naphthalene, diphenylene oxide, benzthiazole, benzisothiazole, thiazole, thiadiazole, thiophene, azobenzene or antrachinone series, X cyan or carbonamide, a remainder A

CH _S
(CH ₂ J ₁₁ CH-QH ₅

where η is 1 or 2 and the other A is water substance or optionally by hydroxy, methoxy ethoxy, hydroxyalkoxy with 2 to 4 carbon atoms, meth oxyäthoxy, acyloxy or acyloxyalkoxy with 2 bL

4 carbon atoms in the alkoxy group are substituted alkyl with 1 to 6 carbon atoms, the acyl group being Have 1 to 4 carbon atoms, a process for the produc- tion of these azo dyes, which is marked thereby net is that one diazonium compounds of amines NEN of the general formula

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 dyestuffs according to Claim 1 for dyeing polyamides and acrylonitrile polymers or polyesters.

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

CH ₃

D-N = N I X

A-HN NH-A

in which D the remainder of a diazo component of benzene, D-NH,

with coupling components of the general form

CH,

(111)

AHN

NHA

converts and hydroxyl-containing dyes ge optionally esterified, where in the formulas D, > and A have the meanings given above, as well as the use of the above th dyes for coloring polyamides, acrylic nitrile polymers or polyesters.

Compared to comparable, from the USA. Patent 2029315 and the German disclosure font 1917 278 known dyes show dii new dyes to an unpredictable extent advantages in the color strength, light and heat setting Ness. The brilliance of the colorations, especially in the red color range, should also be emphasized.

The remainders D derive z. B. of amines de benzene, benzothiazole, benzisothiazole, thiazole-thiadiazole, Thiophene, azobenzene or anthraquinone series.

Substituents for the radicals D of the diazo components are, for example, in the benzene series: chlorine, bromine, nitro, cyano, trifluoromethyl, methylsulfonyl, ethylsulfonyl, phenylsulfonyl, carbonomethoxy, carbobutoxy, carbon - /? - methoxy-ethoxy carbon-β - hydroxy-ethoxy, optionally N-mono or N-disubstituted carboxylic or sulfonamide, methyl, ethyl, methoxy or ethoxy.

N-substituents of the carbon or sulfonamidi are z. B. methyl, ethyl, propyl, butyl, /? - Hy droxyäthyl, γ- hydroxy-propyl, β -methoxy-ethyl, y-methoxypropyl or y-ethoxypropyl and also there pyrrolidide, piperidide or morpholide.

In the azobenzene series: chlorine, bromine, nitro, cyano, methyl, ethyl, methoxy or ethoxy. In the straight cyclic series: chlorine, bromine, nitro, cyano, methyl

y phenyl, methoxy, ethoxy, methyl mercapto. .Carbomethoxy - ethyl mercapto, β - carboethoxybyl mercapto, carbomethoxy, carboethoxy, acetyl, ethylsulfonyl or ethylsulfonyl The remainder D is derived in detail from ζ. B. of hostile amines:

Aniline, o-, m- or p-toluidine, o-, m- or p-nitroaniline, o-, m- or p-cyananiline, 2,4-dicyananiline, o-, m- or p-chloroaniline, o-, m- or p-Br & manilin, 2,4,6-Tribromaniün, 2-Chloro-4-nitroanilIn, 2-bromo-4-nitroaniline, 2-cyano-4-nitroaniline, l-MethylsulTonyl - ^ - nitroaniline, 2-methyl-4-nitroaniline, 2-methoxy-4-nitroaniline, 4-chloro-2-nitroaniline, 4-methyl-2-nitroaniline, 4-methoxy-2-nitroaniline, l-amino ^ -trinuormethyl- ^ chlorobenzene, 2-chloro-5-aminobenzonitrile, 2-amino-5-chlorobenzonitrile, l-amino-2-nitrobenzene-4-sulfonic acid

n-butylamide or - / f-methoxyethylamide, 2,4-dinitroaniline, 2,4-dinitro-6-chloroaniline, 2,4-dinitro-6-bromaniline, 2,4-dinitro-6-cyananiline, l-Amino ^^ dinitrobenzene-o-methylsulfone, 2,6-dichloro-4-nitroaniline, 2,6-dibromo-4-nitroaniline, 2-ChloΓ-6-bromo-4-nitroaniline, 2.6-dicyano-4-nitroaniline, 2-cyano-4-nitro-6-chloroaniline, 2-cyano-4-nitro-6-bromaniline, 1-ardinobenzene-4-methylsulfone, l-Amino ^ jo-dibromo-benzoM-methylsulfone, 1-amino-2 ■ 6-dichlorobenzene-4-methylsulfone, l-amino-2,4-dinitrobenzene-6-carboxylic acid

methyl ester or - / i-methoxyethyl ester, 3,5-dichloroanthranilic acid propyl ester, S ^ -dibromanthranilic acid-zS-methoxyethyl ester, N-acetyl-p-phenylenediamine, 4-amino-acetophenone, 4- or 2-amino-benzophenone,

2- and 4-aminodiphenyl sulfone,

2-, 3- or 4-aminobenzoic acid methyl ester, ethyl ester, propyl ester, butyl ester, -isobutyl ester, - ^ - methoxy-ethyl ester, - / 3-ethoxy-ethyl ester, -methyl-diglycol ester, ethyl diglycol ester, methyl triglycol ester, -ethyl-triglycol ester, - / 3-hydroxyethyl ester, - ^ - acttoxy-ethyl ester, - / 9 - (/? '- hydroxy-ethoxy) -ethyl ester, - / i-hydroxy-propyl ester, -y-hydroxy-propyl ester, -ω-hydroxybutyl ester, -ω-hydroxy-hexyl ester,

5-nitro-anthranilic acid methyl ester, isobutyl ester, methyl diglycol ester, - / I-methoxy-ethyl ester, - / 3-butoxy-ethyl ester, - ^ - acetoxy-ethyl ester,

3- or 4-aminophthalic acid, 5-aminoisophthalic acid or aminoterephthalic 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 dimethylamide,

diethylamide, pyrrolidide, morpholide, N-methyl-N-zJ-hydroxy-ethylamide, 5-amino-isophthalic acid diamide, -bis-y-methoxypropylamide,

Aminoterephthalic acid bis-diethyiamide, 3- or 4-amino-phthalic acid imide, - / I-hydroxy-ethylamide, y-hydroxypropylamide,
S-amino-o-nitro-phthalic acid - ^ - hydroxy-

ethylamide,
2-, 3- or 4-aminobenzosulfonic acid dimethylamide, diethylamide, pyrrolidide, morphobate,
Methylsulfonic acid-2'-, -3'- or -4'-amino-

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

Butylsulfonic acid 2'-, -3'- or -4'-aminophenyl ester,

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

phenylesier,
2-amino-anthraquinone,
1-amino- ^ chloro-anthraquinone, 3- or 4-aminodiphenylene oxide, 2-amino-benzothiazole,
2-amino-6-carboxylic acid methyl ester benzothiazole,

2-Amino-6-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-nitΓO-1,2-benzisothiazole, 3-amino-5-nitro-2,1-benzisothiazole, 3-amino-5-nitro-7-bromo-2, l-benzisothiazole, 2-amino -'ihiazol,
2-amino-5-nitrothiazole,
2-Amino-4-methyl-thiazol-5-ca [ethyl acetate,

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

5-carboxylic acid ester,
2-phenyl-5-amino-l, 3,4-thiadiazole, S-methylmercapto-S-amino-l ^^ thiadiazole, S - ^ - carbomethoxy-ethylmercapto-S-amino-1,2,4-thiadiazole.

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

4-aminoazobenzene,

2 ', 3-dimethyl-4-aminoazobenzene, 3', 2-dimethyl-4-aminoazobenzene, 2,5-dimethyl-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'-chloro-2-methyl-4-aminoazobenzene, 2,5-dimethoxy-4-aminoazobenzene, 4'-chloro-2,5-dimethoxy-4-aminoazobenzene, 4'-nitro-2,5-dimethoxy-4-aminoazobenzene, 4'-chloro-2,5-dimethyl-4-aminoazobenzene, 4'-methoxy-2,5-dimethyl-4-aminoazobenzoI,

4'-nitro-4-aminoazobenzoL
3,5-dibromo-4-aminoazobenzoL
^ '- dichloro-d-aminoazobenzene,
3-methoxy-4-aminoazobenzoL

As residues A are next to

CH ₃
- (CHA-CH-QH ₅

and hydrogen, for example: the alkyl radicals methyl, ethyl propyl or butyl, the hydroxyalkyl radicals, ^ -Hydroxyethyl or -propyl, yJydroxyprop \ 1, fo-hydroxyhexyl, and the residues of the formers

ίο

-CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -OH

- (CH ₂ J ₃ - O - (CHA - OH

the alkoxyalkyl radicals 0-methoxyethyl, y-methoxypropyl, / Ϊ-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 ) ₃ -O-acyl

CH ₂ -CH-O-ACyI

CH ₃

(CH ₂ J ₆ - O-acyl

(CH ₂ J ₂ - O - (CH ₂ J ₂ - O-acyl mono-, di- or trichlorobenzene, tetrahydronira dioxane, dimethylformamide, N-methylpyrrolidec or pyridine can be added.

In the case of esterification with free acids, it can be Be beneficial inorganic or organic catal; sators, e.g. B. HCl gas or p-toluenesulfonic acid, zi add and let the resulting water escape from the real tion mixture by evaporation If acid anhydrides or chlorides are used for esterification, i In special cases, the acids concerned can also be used. So the implementation m Perform acetic anhydride in glacial acetic acid. When using acid chlorides as an esterification medium it is advantageous to add acidic acid to the reaction mixture to add dende means, z. B. sodium carbona or acetate, magnesium oxide or pyridine. As a ver Esterification agents are specifically mentioned, for example: formic acid, acetic acid, chloroacetic acid so like the esters, anhydrides or chlorides of these acids, ethyl chloroformate or diketene continues

Dyes and dye mixtures of the general formula Ia are particularly useful industrially

A ¹ -HN

NH-A ¹

(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 in the event of a weakly to strongly acidic reaction.

The preparation of the coupling components of the general formula III is in principle in German Offenlegungsschrift 2 062 717, 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, or the compounds of the formula I are prepared in principle by the process indicated, if the corresponding ester group is already contained in the coupling component. in some In some cases, however, it is also expedient to introduce the acid radical (acyl) into the finished dye of the formula I. The free acids, their anhydrides, chlorides or esters are suitable for this purpose, in which case it is expedient inert diluents or solvents, such as in the Y nitro, cyano, chlorine, bromine, carbomethoxy, Carboethoxy, / i-methoxycarbethoxy, methylsulfonyl,

Ethylsulfonyl, 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-C ₆ H ₅ CH ₃

and the other oj-hydroxyhexyl, ß-hydroxyethyl, / ϊ-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, which may be used as diazo components, are particularly valuable by nitro, chlorine, bromine, cyano, methyl, methyl mercapto, / i-carbomethoxy-ethyl mercapto, / J-carbo-

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

Some of the particularly valuable diazo components are: S.

4-nitro-aniline,

2-chloro-4-nitro-aniline,

2-bromo-4-nitro-aniline,

2-cyano-4-nitro-aniline, ι ο

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

0-methoxy-ethylamide,
2-amino-benzonitrile,
3-chloro-4-aminobenzonitrile,
2-chloro-5-amino-ben2onitrile,
2-amino-5-chlorobenzonitrile, 20

2,5-dichloro-4-aminobenzonitrile, l-amino-2,4-dicyanobenzene,
1-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-nitΓO-benzonitΓil, 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,
l ^ Dinitro-o-bromo-aniline,

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

1-amino- ^ nitrobenzene ^ -methylsulfone, 1 -Aminc ^ nitrobenzene ^ -äthylsulfon, 4-Methvisulfonyl-anüin,

1-amino ^ -chlorobeiizole ^ methylsulfone, l-Anünc ^ o-dibromobenzene- ^ methylsulfone, 40 l-Ammc ^ o-dichlorobenzene ^ methylsulfone, 2- and 4-amino-benzoic acid esters, 2-amino-5-nitro-benzoic acid estersΓ, 2-amine> -3-chloro-5-iutro-benzoic acid ester, 2-Amino-3,5-dichloro-benzoic acid ester, 45

2-Amino-3,5-dibromo-benzoic acid ester, 2-amino-3,5-diititro-benzoic acid methyl ester or - / I-methoxy-ethyl ester, _;;

2-amino-terephthalic acid diethyl ester,

4-amino-azobenzoL 50

2,3'-dimethyl-4-amino-azobenzene,

2 '^ -Dimethyl- ^ amino-azobenzene, ^ -Dimethyl - ^ - amino-azobenzene,

ibl

^{Of the 55} particularly valuable heterocyclic diazo components, the following should be mentioned:

2-amino-5-nitro-thiazole,

2-amino-4-methyl-5-nitro-thiatol, 2-Amiπo-4-methyl-thiazole-5-carboxylic acid ethyl ester,

2-amino-5-phenyl-1,3,4-thiadiazole 3-phenyl-5-amino-l, 2,4-thiadiazole, 3-methyl-mercapto-5-amino-1,2,4-thiadiazole, S - ^ - carbomethoxy-ethylmercapto-S-amino-

1,2,4-thiadiazole,
3 - ^ - Carboethoxy-äthylmeΓcapto-5-amino-1,2,4-thiadiazole,

2-amino-6-cyano-benzothiazole,
2-Amino-6-carbonsäuΓemethyl-ester-benzthiazole, 2-Amino-6-nitro-benzthiazole,
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-AnUnO-S-OrOm-T-HiIrO-1,2-benzisothiazole,
4-Amino-5-cyano-7-nitro-1,2-benzisothiazole,
4-Amino-5-chloro-7-nitΓO-1,2-benzisothiazole.

The new dyes are yellow to blue and are suitable for dyeing textile materials made from acrylonitrile polymers, synthetic polyamides, cellulose esters such as 2V ₂ or triacetate, and especially synthetic linear polyesters such as polyethylene glycol terephthalate or chemically analogous polymers. The dyeings obtained are of strong color and are distinguished by excellent fastness properties.

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 is 8 hours at stirred about 45 to 55 ° C. Then it is allowed to cool and the mixture is poured in with stirring about 1500 parts of water, 200 parts of concentrated hydrochloric acid 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

H ₃ C

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 mixed with 40 parts / I-Hydroxyäthylamm Stirred at 145 to 160 ° C. for 6 hours. It is then allowed to cool, and the mixture is treated with 100 parts of water and acidified to a pH of about 0 to 1 with hydrochloric acid. One receives - if necessary with the addition of a little glacial acetic acid or dimethylformamide - a solution of the coupling component the likely formula

60

H, C CN

CH ₃

NH-CH ₇ -CH

NH - CH, - CH, - OH

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

409533/406

3 ° C and mixed with a diazonium salt solution, which is obtained as follows:

About 30 parts of concentrated hydrochloric acid (30%) and 80 parts of water are added to 6.9 parts of p-nitroaniline, then the mixture is ^{cooled to 0 °} C. and 15 parts by volume of 23% sodium nitrite solution are added. The mixture is stirred for a further 2 hours, any excess of nitrous acid which may be present is eliminated as usual and the mixture is filtered.

The filtrate is added to the coupling mixture, and sodium acetate or sodium hydroxide solution is then gradually added with stirring so 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 of the likely formula are obtained

H ₃ C

/ - ¹ U γίι / y \

NH - CH ₂ - CH ₂ - OH

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.

Table 1

Coupling component:

H ₃ C CN

NHR,

- CH ₂ - CH - C ₆ H ₅
CH,

example
No. Diazo component CN CN R ₁ H hue yellow 2 CI - ^^^ NHj / -CH ₂ -CH ₂ -OH yellow 3 N = / _Br ^ y _NH j -CH ₂ -CHj-CH ₂ -OH yellow 4th COOCH ₃ -CH ₂ -CH-OH
I. yellow 5 CH ₃ <Γ> —NHj - CH ₂ - CH ₂ - O - CHj-CH ₂ - OH yellow 6th - CH ₂ - CH ₂ - O - CH ₃ yellow 7th H yellow 8th -CH ₂ -CH ₂ -OH .yellow 9 - CH ₂ - CH ₂ -CH ₂ - OH yellow 10 -CH ₂ -CH-OH
I. yellow 11 <Vnh ₂ CH ₃ n = i / - CHj - CHj - O - CHj - CHj - OH yellow 12th TT yellow 13th - CHj-CHj-OH yellow 14th - CH ₂ - CH ₂ - CH ₂ - OH yellow 15th - CHj - CHj - OH yellow 16 CH ₃ - CHj - CHj - O - CHj - CHj - OH yellow 17th - H yellow 18th - CHj-CH ₂ -OH yellow 19th - CHj-CHj -CH ₂ -OH yellow 20th - CHj-CH-OH yellow 21 CH ₃ -CHJ-CH ₃ -O-CHj-CHj-OH yellow 22nd

933

continuation

Diazo component

-CH ₂ -CH ₂ -OH

- CH ₂ - CH ₂ - CH ₂ - OH

-CH ₂ -CH-OH

Br-O-NH ₁

-CH ₁ -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 - OCOCH ₃ OH

- 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
- (CH ₂ J ₆ -OH

orange orange orange orange orange

scfaarlach scarlet fever scarlet fever

-H -CH ₂ -CH ₂ -OH

CH2 CH2 CHj OrI - CH, - CH ₂ - O - CHi- CH ₂ - OH OH

CH ₃ -CH ₂ -CH ₁ -CH ₂ -O-CH ₃

scarlet fever

- CH ₅ -CH ₂ - CH ₂ - OCOCH

scarlet scarlet scarlet

-CH ₂ -CH ₂ -OH

- CH ₂ - CH ₂ - CH ₂ - OH

- CH, - CH ₂ - O - CHj - CHj - OH

yellowish red yellowish red yellowish red

-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, - CH ₂ -O- CH ₂ - CH ₂ - OH

-CH ₂ -CH ₂ -OH

-CH ₂ -CH ₂ CH ₂ -OH

-CK ₇ -CHj -O-CH ₂ -CH ₂ -OH

continuation

example
No. Diazo component / CF ₃ -NH, R ₂ -CH ₂ -CHj-OH hue yellow COOC ₂ H ₅ Cl - / "" V-NH ₂ -CHj-CHj-CH ₂ -OH yellow 62 A. ™ \ = / Cl- ^ T ρ -NH ₂ -CH ₂ -CH ₂ -O-CHj-CHj-OH yellow 63 rV ^NH > CH ₂ - CHj - OH 64 Y I.
/ N \ H yellow COOCjH ₅ -CH ₂ -CH ₂ -OH yellow 65 SO ₃ CH ₃ - CH ₂ - CH ₂ - CH ₂ - OH yellow 66 ^ _P ^ NH ₂ -CH ₂ -CH ₂ - CH ₂ -O-CH ₃ yellow 67 -CH ₂ -CH ₂ -OH yellow 68 € y —N — N— <f 1> —NH ₂ - CH ₂ - CHj - CHj - OH yellow 69 COOCH ₃ -CH ₂ -CH ₂ -O-CHj-CH ₂ -OH yellow 70 Br - ζ \ --NH ₂ - H yellow 71 -CH ₂ CH ₂ -OH yellow 72 Br -CH ₂ -CHj-CH ₂ -OH yellow 73 HO
I .—>. -CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -OH yellow 74 CH ₃ - N - S - f V - NH ₂ -CH ₂ -CH ₂ -O-CH ₃ yellow 75 Il N = /
O -CH ₂ -CH ₂ -CH ₂ -OH yellowish red 76 -CH ₂ -CH ₂ -OH yellowish red 77 78 O / ^Br - CH ₂ - CHj - CH ₂ - OH orange C ₂ H ₅ - OC - \ S - NH ₂ - CH ₂ - CH ₂ -O- CH ₂ -CH ₂ - OH orange 79 80 -CH ₂ -CH ₂ -OH yellow CH ₂ -CH ₂ -O-CH ₃ CH ₂ CH ₂ CH ₂ OH yellow 81 CH,
I. -CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -OH yellow 82 -CH ₂ -CH ₂ -OH golden yellow 83 -CH ₂ -CH ₂ -CH ₂ -OH golden yellow 84 CH, -O —CH, -CH, -N —C -V> - OH 85 ! it N = -
HO -CH ₂ -CH
CH ₃ golden yellow _QH , _ _N _ _C _ ^ _ _{NH |} , - CH ₂ - CH ₂ - O - CH ₂ - CH ₂ - OH 86 HO golden yellow -CH ₂ -CH ₂ -OH 87 - CH ₂ - CH ₂ - CH ₂ - OH eeib - CH ₂ -CH ₂ -O -CHj -CH ₂ -OH eelb 88 -CH ₂ -CH, -OH yellow 89 - CH, - CH ₂ - CH, - OH yellow 90 -CH ₂ -CH ₂ -OH yellow 91 - CHj -CHj-CHj-OH yellow 92 yellow 93 94

Coupling component:

NH - CH ₂ - CH - C ₆ H ₅ CH ₃

16

example
No. Diazo component R, hue 95
96
97 COOCH ₃ -CH ₂ -CH ₂ -OH
- CH ₂ - CH ₂ - CH ₂ - OH
- H yellow
yellow
yellow 98
99
100 CN -CH ₂ -CH ₂ -OH
- CH ₂ - CH ₂ - CH ₂ - OH
- CH ₂ - CH ₂ - CH ₂ - O - (CH ₂ ) ₂ OH yellow
yellow
yellow 101
102
103 / CN
cH ^ y- ^NH > -CH ₂ -CH ₂ -OH
- CH ₂ - CH ₂ - CH ₂ - OH
-CH ₂ -CH 2 -O-CH ₂ -CH 2 -OH yellow
golden yellow
yellow 104
105
106 Ο ₂ Ν- / ~ Λ> —NH ₂ -CH ₂ -CH ₂ -OH
-CH ₂ -CH ₂ -CH ₂ -OH
- CH ₇ - CH ₂ - O - ( _{CH 2) 2} OH orange
orange
orange 107
108 CN
. _Br _ ^ y. _N H ₂
Br - CH ₂ - CH ₂ - CH ₂ - OH
- CH ₂ - CH ₂ - O - CH ₂ - CH ₂ - OH orange
orange 109
110 Cl
OjN - / ~ \ ~ NH ₂ -CH ₂ -CH ₂ -OH
-CH ₂ -CH 2 -CH ₂ -OH Sharlacr
Sharlact Ul
112 Cl - / "V-NH ₂ -CH ₂ -CH ₂ -CH ₂ -OH
-CH ₂ -CHz-O- (CHz) ₂ OH yellow
yellow Ϊ13
114
115 CH ₂ -CH ₂ -OH
/ N _x
° \ / °
<C ~> -NH,
- ^. fir C-, H2 C H2 OH
- CH ₂ - CH ₂ - CH ₂ - OH
OH ₂ CH 2 CH 2 CH 3 yellow
yellow
yellow

_R. 111 /;

B e 1 s ρ 1 e 1 110

19.5 parts of 3 - amino - 5 - nitro - 2,1 - benzisothiazole are added in portions at 15 to 25 ° C. with stirring to about 75 to 85 parts of 96% sulfuric acid

given, and the mixture is then cooled to 0 bis. 32.5 parts of 23% strength nitrosylsulfuric acid are _{then added dropwise at this temperature.} The azotization is complete after about 3 to 4 hours of stirring at 0 to 5 ° C. Now you give the Tue

409 53;

ί '.

2 226 93p

17 *

pium salt mixture to a ^{solution or suspension, cooled to 0} ° C., of 34 parts of the coupling component of the formula

CN

CH,

NH-CH ₂ -CH-C ₆ H ₅

NH-CH ₂ -CH ₂ -CH ₂ - Q-CH ₃

in 50 parts of 30% hydrochloric acid, 500 parts of water that the ^. ^ and 150 parts of glacial acetic acid. During the coupling does not exceed 5 ° C and derp ^ if you gradually add ice and sodium acetate so about 2 is the precipitated burst of color

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 is stirred with about 200 parts of 85 to 95% sulfuric acid for 5 hours at 80 to 100 ⁰ C. The mixture is then poured into 1500 parts of ice water and the precipitated dye of the formula is filtered off

CONH ₂

CH ₃

NH-CH ₂ -CH-C ₆ H ₅

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 colors polyethylene terephthalate fabric in blue tones.

Table 3

Coupling component:

Example no.

H, C

CN

(V- NH - CH ₂ - CH - C ₆ H _5> N

NH-R ₂

Diazo component -CH ₂ - CH ₂ - OH hue CH2 CH2 CH2 OH yellowish red -CH ₂ -CH-OH yellowish red I. yellowishigrol CN CH, / -CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -OH ~ i -M— <? % NH - CH ₂ - CH ₂ - CH ₂ - OCHO yellowish red J ₂ IN V y IN Π ₂ H yellowish red - (CH ₂ J ₆ -OH Scarlet fever -CH ₂ -CH ₂ -O-COCH ₃ yellowish red yellowish red

continuation

game Diazo component , - / _O2N _y ~ v_ _NHj / f ~ C Br R = -CH ₂ -CH ₂ -OH Hue . 1 126 O ₂ N- ^ fy ~ NH ₂ OjN- ^ V-NHj - CH ₂ - CH, - CH ₂ - OH Scarlet fever Ibraunstichi 127 Br COOCH ₂ - CH ₂ - OCH ₃ - GH, -CH-OH Scarlet fever (Scarlet fever 128 Cl Cl CH ₃ Scarlet fever j O ₂ N - <^^ - NH, NO ₂ - CH ₂ -CHj-O-CHj-CHj-OH 129 O ₂ N - <? ρ -NH ₂ H Scarlet fever 130 COOCH, N
Cl Scarlet fever 131 ON ^ X-NH - CHj-CHj-OH ruby 132 N = / ² / - CH ₂ - CH 1 - CH 1 - OH ruby 133 CN COOCH, -CH ₂ -CH-OH ruby 134 J-C _ON _ ^ K_ _NH " O ₂ N - € ρ - NH ₂ i
CH ₃ ruby O ₂ N ^^ y ~ NHj - CH ₁ - CH 2 - O - CH ₂ - CH, - OH 135 ^ N
XIr Br Br - CHj - CHj - O - CH ₃ ruby 136 DT Cl - CH ₂ - CH ₂ - CH ₂ -O- CH ₃ ruby 137 - CHj - CHj - O - COCH ₃ ruby 138 OjN-V)> - NHj - H ruby 139 ^ N - CHj-CHj-OH ruby 140 - CHj - CHj - CH ₂ - OH ruby 141 CN - CHj-CH-OH ruby 142 I. ruby CH ₃ - CHj - CHj - Ο - CHj - CHj - OH 143 -CH ₂ -CHj-O-CH ₃ ruby 144 -C ₂ H ₅ ruby 145 - CHj-CHj-OH ruby 146 - CHj - CHj - CHj - OH Red 147 - CH ₂ - CH ₂ - O - CH ₂ - CH 1 - OH Red 148 Red -CH ₂ -CH ₃ -OH 149 -CH ₂ -CH ₂ -CHj-OH Red 150 -CHJ-CHj-O-CH _2-OH -CHJ Red 151 - CH ₁ - CH 2 - OH Red 152 - CH ₂ - CH ₂ - CH ₂ - OH • Red 153 Red - I-T 154 -CH ₂ -CH ₂ -OH Red 155 - CHj-CHj-CHj-OH Red 156 -CHj-CHj-O-CH ₂ -CH ₂ -OH Red 157 -CH ₂ -CH ₂ -O-CH ₃ Red 158 -CH ₂ -CH ₂ -OH Red 159 - CH ₂ - CH ₂ - CH ₂ - OH 160 -CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -OH 161 - CH ₂ - CH ₂ -O- COCH ₃ 162 - CHj-CHj-OH 163 - CHj - CHj - CHj - OH 164 -CH ₂ -CH-OH 165 I. CHj -CH ₂ -CHj-O-CHj -CHj-OH 166 -CH ₂ -CH ₂ -OH 167 - CHj - CHj - CHj - OH brownish 168 - CHj - CHj - CHj - O - CH ₃ Scarlet fever 169 , braunstichij Scarlet fever

example

No.

170 171 172 173

174 175

176 177 178

179 180 181

182 183 184

185 186 187 188

189

190 191 192

193 194 195 196

197

198 199

200 201

21

continuation

ti

Diazo component

CN

Cl

C ₄ H ₉ In) NHC

Cl

Br

V-NH ₂ Br

SO ₂ CH ₃

NH ₂

NH ₂

O ₂ N

R,

-CH ₂ -CH ₂ -OH

-CH ₂ -CH ₂ -CH ₂ -OH

- CH ₂ - CH ₂ - O - CH ₂ - CH ₂ - OH

~ CHt CHj CH2 O CH3

-CH ₂ -CH ₂ -OH
-CH ₂ -CH ₂ -CH ₂ -OH

Br (Cl)

O NH ₂

-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 -CII 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 ₃
- (CH ₂ ) JO- (CHj) ₄ -OH

Color ion

bluishigrol bluish tinted red blue-tinted red bluish-tinted red

Red Red

red red red

yellow yellow yellow

yellow yellow yellow

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
- (CHj) ₆ -OH

- (GH ₂ ) JO- (CH ₂ U-OH
-CH ₂ -CH ₂ -CH ₂ -OC-CH ₃

-CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -OH

SO ₂ C ₁₁ H ₅ 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 ₂ -CH ₂ -O-CHj _{-CH 2} -OH

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 yellow

example

No.

202 203

204 205 206 207

208 209 210

211

212 213

214

215 216 217 2Ϊ8 219

23

2fl6 933

continuation

24

Dia / ocomponenle

NHj

no,

O ₂ NZ ^ V-NH ₂ Cl

, NO ₂ O ₂ N- <> -NH ₂

O ₂ N

NH,

CH ₃ OC O

NC

> -NH ₂

O ₂ N - "(^ V" ^NH *

hue

- CH ₂ - CH ₂ - O - CH ₂ - CH ₂ - OH - (CH ₂ Jj-OH

-CH ₂ -CH ₂ -OH CH ₂ -CHj-CH ₂ -OH

CH ₂ - CH ₂ - O - CH ₂ - CH ₂ - OH

(CH ₂ ) ₃ -OH CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -OH

-CH ₂ -CH ₂ -CH ₂ -OH -CH ₂ -CH ₂ -OH

-CH ₂ -CH ₂ -OH

CH ₂ -CH ₂ -OH CH ₂ - CH ₂ - C CH ₂ - CH ₂ - O (CHJO (C

OH

CH ₂ - CH ₂ - OH K - OH

yellow yellow

bluish red bluish red bluish red bluish red

bluish red bluish red bluish red

Scarlet fever

Scarlet fever

Scarlet fever

bluish-tan red bluish-tan-red bluish-tan-red bluish-tan-red

220 221 222

223 224

225 226

227

O ₂ N- / ~ \ -NH,

N Br

O ₂ N - ^ ~ ") ~ NH,

S '; ■ N CN

O ₂ N - <· ("'^;'_{;. - NH 2} S V-

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

OH

violet violet bluish red

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

SO, C, H <

Ο, Ν - ('- NH; - CH ₂ - CH ₂ - CH ₂ - OH -CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -OH

- CH, -CH, -CH, -OH

violet violet

violet
violet

ruby

example

No.

25th

continuation

Diazo component

Coupling component:

Table 4 H ₃ C CN

O-NH-R,> N

NH - CH ₂ - CH CH ₃

hue

228 CH ₃ - S -Ij- 0 N
\ / L-NH ₂ S. pCN ³ Ii 1 -N NC H - - H. orange 229 —N Il CH ₃ -Ij N
O ₂ N -4 I-NH, C ₂ H ₅ -OCI J-NH ₂ O ₂ N -4 y - NH ₂
S. - CH ₂ - CH 1 - OH orange 230 \ S
S. Il \ /
0 ^p QH ₅
η N - CH ₂ - CHj - CHj - OK orange 231 NO ₂ Jpi -CH ₂ -CH ₂ -O-CHj -CHj-OH orange 232 N L CIl ₃ ι C. - <ZV NH ₂ C = C S NH, PU / * ^ I4 C \ U orange 233 CH ₃ - O - C-4 CN -CH ₂ -CH ₂ -CH ₂ -OH orange 234 S. NO ₂ -CH ₂ -CH-OH orange 235 . 1-NH ₁ _ / CH ₃
- CH ₂ - CH ₂ - O - CH ₂ - CH 1 - OH orange 236 H V O ₂ N -fV- NHj orange 237 0 ^b -CH ₂ -CH ₂ -OH violet 238 CH ₃ -, CN - CHj - CHj - CHj - OH violet 239 -CH ₂ -CHj -O-CH ₂ -CH ₂ -OH violet 240 -CH ₂ -CH ₂ -OH bluish red 241 -CH ₂ -CHj -CHj-OH bluish red 242 - CH ₂ -CH ₂ - 0 - CHj- CH ₂ - OH bluish red 243 - CH, -CH-OH bluish red I.
CH, 244 -CH ₂ -CH ₂ -OH bluish red 245 -CH ₂ -CH ₂ -CH ₂ -OH bluish red 246 -CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -OH bluish red 247 - CH ₂ - CH 2 - CH ₁ - OH Red 248 CH2 CH2 - OH bluish red 249 - CH ₂ - CH ₂ - CH ₂ - OH bluish red 250 H bluish red - CH, -CHj-OH 251 - CH, - CH ₂ - CH ₂ - OH violet 252 violet -CH ₂ -CHj-CHj-OH 253 reddish blue

H"

continuation

example
No. Diazokomponeiue Br
ζ Br / ■ hue 254 y ~ \. ",,, ^ V-NH, Cri2 CH2 OH Scarlet fever 255 - <^ ν-ΝΗ ₂ Cri2 0ri2 v_ri2 QVl Scarlet fever 256 O ₂ N \ f
N - CH ₂ - CH ₂ - O - CH ₂ - CH ₂ - Scarlet fever 257 Γγτ ^ΝΗι - H Scarlet fever 258 CN -CH ₂ -CH ₂ -OH yellowish red 259 N - CH ₂ - CH ₂ - O - COCH ₃ yellowish red 260 O "M Cri2 CrT ^ "-" "Ca * 2 OH. yellowish red 261 W ₂ PI - CH ₂ - CH ₂ - 0 - CH ₂ - CH ₂ - yellowish red 262 yellowish red 263 SO ₂ CH ₃ yellowish tinted 264 ~ ^>"ΝΗ ₂ Red 265 O ₂ N -OH Red 266 CN Red 267 ruby 268 - \\ - NH ₂ ruby 269 O ₂ N Br ruby -OH 270 CN
/ - CH ₂ - CH ₂ - 0 - CH ₂ -CH ₂ OCHO ruby 271 - / V-NH - (CH ₂ ) ₆ OH Red 272 - <^> ΝΗ ₂ - CH ₂ - CH ₂ - CH ₂ - OH ruby 273 O ₂ N N
Cl CHj CH2 OH ruby 274 NO ₂ -H ruby CH2 CH2 OH 275 O ₂ N SO ₂ CH ₃ - CH ₂ - CH ₂ - CH ₂ - OH violet -CH ₂ -CH-OH 276 O ₂ N S ^ 1
CH ₃ ruby 277 N - CH ₂ - CH ₂ - O - CH ₂ - CH ₂ - ruby -CH ₂ -CH ₂ -OH CH2 CH2 CH2 OH OH2 C-H2 O CH2 CH2 ~ 278 O ₂ N - (CH _{2) 3} - 0- (CH _{2) 4} - OH violet 279 violet - CH ₂ - CH ₂ - CH ₂ - OH 280 O ₂ N- reddish blue 281 - CH ₂ - CH ₂ - CH ₂ - OH reddish blue - CH ₂ - CH ₂ - O - CH ₂ - CH ₂ - -CH ₂ -CH ₂ -CH ₂ -OH CH2 CH2 O CH2 CH? ~ - CH ₂ - CH ₂ - CH ₂ - OH - CH ₂ - CH ₂ - O - CH ₂ - CH ₂ - -OH -OH -OH -OH -OH

29

continuation

30th

example
No. Diazo component NO ₂ R. l-iirbtou blue D ₁ N - (Λ —τ— NH, O ₂ N ~ - / ~ \ - NH ₂ 282 Il S N = / - CH ₂ - CH ₂ - O - CH ₂ - CH ₂ - OH T ^ NO ₂ ' Red Cl Red 283 H Red 284 Cl -CH ₂ -CH ₂ -OH Red 285 NO ₂ -CHj-CH ₂ -CH ₂ -OH 286 / -ill / ^ TJT / Λ ΛΊ-Γ Γ * 11 Γ \ Ή
V- * ri2 ^ -Ή-2 vJ * - t * 2 ^ Γΐ2 ν ^ .Η bluish red bluish red 287 CN / - »ir /" ¹ O / ^ TI f "\ IJ
V ^ 1 * 2 ^ -Ή.2 ^ - '■ Γΐ2 vJrl 288 COOCH ₃ - CH ₂ - CH ₂ - O - CH ₂ - CH ₂ - OH O ₂ N- ^ NH ₂ bluish red bluish red 289 - CHj-CHj-CHj-OH 290 - CHj-CH ₂ -O- (CH ₂ ) jOH Red Red 291 - CHj - CHj - CHj - OH 292 - CH ₂ - CH ₂ - O - CH ₂ - CH ₂ - OH

Table 5

Coupling component:

H ₃ C CONH ₂

% ~ \ - NH - CH ₂ -CH - QH ₅

> N

NH-R ₂

CH ₃

example
No. Diazo component R2 hue Red 293 α - CH ₂ - CH ₂ - O - COCH ₃ Red 294 - CH ₂ - CH ₂ - CHj - O - COCH ₃ Red 295 O ₂ NZ ^ -NH ₂ - CHj - CHj - CH ₂ - OH Red 296 - CH ₂ -CHj-O-CH ₃ bluish red 297 - CH ₂ - CH ₂ - OCOCH ₃ bluish red 298 CN - CH ₂ - CH ₂ - CH ₂ - OCOCH ₃ bluish gray 299 - CH ₂ - CH ₂ - CH j - OH bluish red 300 O ₂ N- / VnH, - CH ₂ -CH ₂ -O-Ch ₂ -CH ₂ -OCOCH ₃ bluish red 301 -CH ₂ -CH ₂ -O-CH ₂ -CHj-OH bluish red 302 - CH ₂ -CH ₂ - O - CH ₃ red violet 303 - CH ₂ - CH ₂ - CH ₂ - OCOCH ₃ red-violet 304 CN - CH ₂ -CH ₂ - CH ₂ - OH red-violet 305 - CH ₂ -CH ₂ -O-CHj-CH ₂ -OCOCH ₃ red-violet 306 - CH ₂ - CHj - O - CH ₂ - CHj - OH red-violet 307 Br -CH ₂ -CH ₃ red-violet 308 - CH ₂ - CH ₂ - CH ₂ - O - CH ₃

4 ■

31

226 933

continuation

!
example
No. Diazocoirnoneme R ₂ hue blue 309 - CH _{2 - CH 2} - O - COCH ₂ - COCH ₃ blue 310 - CH ₂ - CH ₂ - OCOCH ₃ blue 311 "~ - ~ CHj CH2 - CHj O COCH3 blue 312 Ο, Ν - / S ρ NH ₂ - CH ₂ - CH ₂ - CH ₂ - OH blue 313 Il S - CH ₂ - CH ₂ - O - CH ₃ blue 314 N - CH2 CH2 CH2 O C2H5 blue 315 - CH ₂ -CH ₂ -O-CH ₂ -Ch ₂ -OCHO blue 316 - CH _{2 - CH 2} - O - CH ₂ - CH ₂ - OH blue 317 -CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -O-COCh ₃ O ₂ N - / S-. . | NH, greenish blue 318 Br - CH ₂ -Ch ₂ -O-CH ₂ -CH ₂ -O-COCH ₃

Coupling component:

Table 6

CH ₃ NH - CH ₂ - CH ₂ - CH - C ₆ H ₅

NH-R ₂

example
No. Diazo component CN
/ R ₂ H hue 319 V-NH ₂ -CH ₂ -CH ₂ -OH Scarlet fever 320 CH2 CH2 V - H2 OH fire red 321 OH Red CH2 CH
CH ₃ 322 O ₂ N - / -CH ₂ -CH ₂ -O-CH ₂ -CH ₂ -OH yellowish red H 323 V = / ² -CH ₂ -CH ₂ -OH yellowish red 324 - CH ₂ - CH ₂ - CH ₂ - OH Scarlet fever 325 ^ V-NH - CH ₂ - CH ₂ -O- CH ₂ - CH ₂ - OH Scarlet fever 326 O ₂ N- ^ H Scarlet fever 327 -CH ₂ -CH ₂ -OH Scarlet fever 328 CN - CH ₂ - CH ₂ - CH ₂ - OH orange 329 _o _j - CH, - CH ₂ -O- CH ₂ - CH ₂ - OH orange 330 H orange 331 - CH ₂ CH ₂ OH orange 332 CHj CH ₂ CH ₂ OH bluish red 333 O ₂ N - <( ruby 334 ruby

continuation

34

If

example
No Dui / nkompm ^ ciUc R, hue Red
Red
Red 335
336
337 NO ₂
O ₂ N- ^ J) -NH ₂ H
-CH ₂ -CH ₂ -OH
- CH ₂ - CH ₂ - CH ₂ - OH yellow
yellow 338
339 CN 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: s ■■ · .V, l.i'Azo dyes with 2,6-diaminopyridines as Coupling components characterized by the general formula D-N = N