DE2162419C3 - Trisazo dyes and their iron complexes, and their use for dyeing and printing leather - Google Patents

Description

2. Process for the production of Trisa / ofarbstoffen and their iron complexes, marked thereby . that one on monoazo dyes of the formula

R,

OH

HO

OH

20th

in which R ₁ and R _{2 are} those specified in claim I.

> —NH - \

NO,

SO., H
Have meaning diazotized amines of the formula

HO R ₄

H, N - ■ (

in which R _{1 and R 4 have} the meaning given in claim 1, and diazotized 4-amino-4-nitrodiphenylamine-2'-sulfonic acid has an alkaline coupling and, if appropriate, then converted into iron complex by adding iron! HD salts. 3. A process for dyeing and printing leather, characterized in that dyes according to Claim 1 are used.

The invention relates to valuable trisazo dyes of the general formula

OH R ₄

OH

OH

Ν —Ν

OH

- N - N R. »

Nile

NO,

S 0.11

k \ the R ₁ denotes the sulfonic acid group. R ₂ for sit, diazotized amines of the formula hydrogen. Chlorine. Nitro or the sulfonic acid group 55 blows, R ₁ chlorine. Nitro or the sulfonic acid group and T ^ ₄ hydrogen. Chlorine. Nitro or the sulfonic acid group means, and their iron complexes.

These new dyes are obtained by adding H ₂ N

one on monoazo dyes of the Fonne!

Uli)

R,

OH

HO

N ■ - = - N

OH

in which R, and R _{2 have} the abovementioned meaning where R ₁ and R _{4 have} the meaning given above, have an alkaline coupling and the disazo dyes thus obtained are coupled in the alkaline range with diazotized 4-amino-4-nitrodiphenylamine-2'-sulfonic acid (IV) .

Suitable diazo components «(!!!) are for example

wise:

2-amino-4-sullophenoi.

2-amino-4-sulfo-6-chlorophenol.
^ -Amino ^ -nitro-o-sulfophenol.
2-amino-4-chlorophenol.
2-amino-4-nitrophenol,
2-amino-4,6-dichlorophenol.
2-Amino-4-nitro-6-chlorophenol and
2-amino-4,6-dinilrophenol.

The monoazo dyes ill) are coupled by coupling diazotized amines of the formula

OU

- NU,

R,

in which R, and R, the meaning given above own, shown in an alkaline medium on resorcinol.

The trisazo dyes obtained in this way are optionally isolated by salting out and removed if necessary after dissolving in water at the boiling point by adding iron-releasing agents, preferred Kisen (III) salts converted into their liise complexes in an acetic acid medium. The dyes, in particular their iron complexes color leather in a yellow-tinged dark brown Shades. In addition to good light-curing properties, the colorations also have other good ones coloristic properties, such as good acid fastness. Alkali fastness. Acid resistance. Click justice and Solvent-proof The dyes have a good water solubility and colors well from hard Water.

Compared to other comparable dyes of the According to the state of the art, the new dyes have a number of application advantages.

In comparison / u the dye of Example 15 of the DT-OS 1644 331 (mclall-free and iron complex) shows z. B. a constitutionally similar crfindungsgemäücr Dye the better acid and alkali fastness.

The dye of the formula IX of FR-OS 2O57O2X Finally, a closest comparable dye is the present invention in terms of lightness superior to chrome cowhide colors.

example 1

24 "i> ilcdcr6-nitro-2-aminii-l-plienol-4-sulfonic acid are dia / olieit and alkaline in a known manner coupled to 11 parts of resorcinol. On the so obtained Monoazo dye is coupled first, also alkaline, the diazo compound of 20 parts of 4,6-dinitro-2-aminvi-! -phenol and then the diazo compound of 31 parts of 4-amino-4'-nitro-diphenvlamine-2'-sulfoiic acid. The dye is isolated by adding sodium chloride, redissolved and at an elevated temperature in weakly acidic medium by adding 27 parts of FeCl, · 6H, O to the iron complex convicted. The dye ίο, which is isolated by salting out, has good solubility and dyes leather in a yellow-tinged dark brown Tones. The colorations have generally good coloristic properties a good loan technology.

Example 2

19 parts of 2-amino-1-phenol-4-sulfonic acid are coupled to 11 parts of resorcinol in a double and alkaline manner. The diazo compounds 19 parts of 4-nitro-6-chloro-2-amino-1-phenol and 31 parts of 4-amino-4-nitro-diphenyl-amine-2'-sulfonic acid are likewise coupled under alkaline conditions to the monoazo dye thus obtained. After isolation by salting out, the dyes are redissolved and converted into their fish complexes in a known manner _{by adding 26 parts of FeCl, 6H 2 O.}

Example 3

19 parts of 2-amino-1-phenol-4-sulfonic acid are coupled diazotically and alkaline to 11 parts of resorcinol. The diazo compounds are also coupled under alkaline conditions to the monoazo dye thus obtained of 20 parts of 4,6-dinitro-2-amino-1-phenol and 31 parts of 4-amino-4'-nitro-diphenylamine-2'-sulfonic acid.

After isolation by salting out, the As in Example 1, dyestuffs were converted into their fleece complexes.

The dyes obtained have good coloristic properties. They color leather in yellowish dark brown Ions.

Example 4

19 parts of 2-amino-1-phenol-4-sulfonic acid are diazotized and coupled under alkaline conditions to 11 parts of resorcinol.

The 18 "diazo compounds are also coupled in an alkaline manner to the monoazo solid obtained in this way 4.6-dichloro-2-amino-l-phenol and 31 "file 4-Amino-4'-nitro-diphcnylamine-2'-sulfonic acid and performs this as in Example 1 after isolation and redissolve in their iron complex compounds. Dyes are obtained which give leather a yellowish dark brown Dye color shades, but with a slightly more reddish shade compared to the dyes of the previous examples with the same coloristic properties.

Claims (1)

Claims: Trisazo dyes of the general formula R ₁ OH OH .-OH in which R _{1 is} the sulfonic acid group. R ₂ for hydrogen. Chlorine. Nitro or the sulfonic acid group, R, chlorine. Nitro or the sulfonic acid group and R ₄ hydrogen. Chlorine. Nitro or the sulfonic acid group means, and their iron complex compounds.