DE2110771C3 - Trisazo dyes and their use for dyeing hydroxyl-containing and nitrogen-containing fiber materials - Google Patents

Description

A '- N = N

H, N OH

"i i

Y \ N = N

(SO., H) "

or aminohydroxyphenyl and
η = 1 or 2 _t

where the rings C and D _{can be substituted by Cl -C 4} -AllCyI, CI or Br.

2. Trisazo dyes of the formula

V CONH

N = N B

wherein

A '= nitrophenyl, chlorophenyl, methylphenyl

and
B and η have the meaning given in formula (1)

to have.

3. Use of the trisazo dyes of claims 1 to 2 for dyeing hydroxyl-containing and nitrogenous fiber materials.

The present invention relates to trisazo dyes of the general formula

H ₂ N OH

Λ NN

N N

CONlI

D / NNB

(SO ₁ H).

wherein

A = phenyl, optionally by halogen, methyl, ethyl, methoxy. Ethoxy, nitro or sulfo substituted,

B = hydroxyphenyl, diaminophenyl or aminohydroxyphenyl optionally substituted by methyl or ethyl and

η = 1 or 2,

where the rings C and D by Ci - G-alkyl, CI or Br can be substituted.

Suitable radicals A are, for example, phenyl, halophenyl such as chlorophenyl, bromophenyl and alkylphenyl such as methylphenyl, ethylphenyl, alkoxyphenyl such as methoxyphenyl, ethoxyphenyl, nitrophenyl, sulfophenyl.

Suitable radicals B are, for example, hydroxyphenyl, hydroxymethylphenyl, hydroxy-ihhylphenyl, aminohydroxyphenyl, Diaminophenyl, diaminomethylphenyi

Examples of substitutes for rings C and D include methyl, ethyl, propyl and butyl as well as chlorine and bromine.

Preferred dyes are those of the formula

H ₂ N OH

; j

A '-N =

N = N

LONH

-N = N-B

wherein

A '= nilrophenyl, chlorophenyl, methylphenyl and B and h have the meaning given in formula (1).

The new dyes of the form! (I) is obtained from the formula known manner by acidic coupling of amines of the formula

A-NH ₂
aurAminohydroxynapIilhalinsuironsäuren of the formula AN = N-

HO NH-,

Subsequent half-sided coupling with an lactrazotized Amine of the formula

(SO ₃ H) _n

(IV)

/ '"" ■ "M ₂ IN- ^ C> - CONH

where Ii = 1 or 2, to monoazo dyes η to disazo dyes of the formula

H-, N OH

^ dV-NH ₂ (VI)

N = N

CONH

(VII)

(SO.HL

where X is an anion, preferably the anion of an inorganic acid such as sulfuric acid or hydrochloric acid and subsequent coupling with coupling components

B H (VIII)

in which B hydroxyphenyl, diaminophenyl or aminohydroxyphenyl which is optionally substituted by alkyl means.

Suitable amines (III) are, for example, aniline, 2- ^ 10 ^^ 1 ^, 1-0110 ^ 3 ™ ^, 4-chloro-aniline, I-aminobenzo '.- 2-s'.' Ionic acid, J5

1-aminobenzene-3-sulfonic acid, 1-aminobenzene-4-sulfonic acid, l-amino-2-methylbenzene,

I - amino-4-methyl-benzoI, 1-amino-2-nitro-benzene, I-amino-4-nitro-benzene, -to

1 - amino-4-methoxy-benzene.
Suitable amino-hydroxynaphthalenesulfonic acids (IV) are, for example

l-amino-e-hydroxy-naphthalenO.ö-disulfon-

acid, 4>

l-Amino-S-hydroxy-naphthalene ^ .ö-disuIfon-

acid,
l-Amino-S-hydroxy-naphthalene ^ -sulfonic acid.

Suitable diamines (IV) are, for example:
4-Amino-benzoyI-4'-amino-anilide
4-Amino-2-chloro-benzoyl-4'-amino-aniIide
4-Amino-3-methyl-benzoyI-4'-amino-arilide
4-Amino-benzoyl-4-amino-2'-chloro-aniIide
4-Amino-benzoyl-4'-amino-3'-methyl-anilide.
Suitable coupling components (VIII) are, for example

Phenol, methylphenol, ethylphenoi,
1,3-diaminobenzene, l-amino-3-hydroxybenzoI,
1 ^ -diamino ^ -methylbenzene.

The coupling of (V) with (VI) and of (VII) with (VIII) takes place in an aqueous-alkaline manner in a manner known per se Medium.

The new dyes are ideal for dyeing hydroxyl-containing and nitrogen-containing natural and synthetic fiber materials, for example cellulose fibers in all processing states, especially cotton and regenerated cellulose, as well as wool, semi-wool, silk, nylon, leather and paper. Green to black dyeings with good fastness properties, in particular good water and perspiration fastness properties, are obtained after aftertreatment with cation-active auxiliaries.
The dye of the formula

O ₃ N

H, N C) H

kJJ

N-N

J V con ONH

N N

C) H

SO ₁ H

shows the closest comparable known from British Patent 3 38111, Example Dye the surprising advantage of the better e> o Drawability on cotton,

example 1

13.8 parts of l-'Amino ^ nitro-benzene are used in the usual Wise diazolized neutral solution of 31.9 parts of 1-amino-8-hydroxynaDhthälin-3.6-disülföhsäUfe run in 150 ml of water.

After stirring overnight, the coupling is complete. The coupling is brought into solution at pH 7 by sprinkling in 15 parts of sodium carbonate. 22.7 parts now be 4-Aminobenzpyl-4'-aminoanilide tetrazotized in a mixture of 23 parts water and 56 parts of 30% strength aqueous hydrochloric acid at O to 1O ⁰ C with 13.8 parts of sodium nitrate. After the first coupling has been admixed with 20 parts of sodium carbonate, it runs to the tetrazotization of the 4 * aminobenzoyl-4'-afrtinöanilids previously congoneutrai with sodium carbonate solution. After about 15 minutes the half-page is

Clutch finished. Then a solution of 9.4 is added Parts of phenol in 100 parts of water and 17 parts of sodium carbonate. The coupling stirs overnight Then the dye is sown with rock salt, filtered off and dried. The dye dyes cotton in green tone,

Other dyes manufactured according to the invention are summarized in the table below according to components and details of the color shades.

Example A-NH ₂
No.

HO NH ₂

H, N

-CONH-

NH ₂

(SO ₃ H), HB

hue

on

cotton

4-nitro-1-amino-8-hydroxyaniline naphthalene-3,6-di-

sulfonic acid

2-chloro-l-amino-8-hydroxyaniline naphthalene-3,6-di-

sulfonic acid 4-aminobenzoyl-4'-aminoanilide

4-aminobenzoyl-4'-aminoaniIide

1,3-diaminobenzene

1,3-diarninobenzene

green-

sure-

black

black

Staining example

In a staining beaker with a capacity of 500 ml, which is in a heatable water bath, 260 ml of water at 50 to 60 ° C are placed and 10 ml of 10% Sodium sulfate solution and 1 ml of 10% sodium carbonate solution added. 0.25 g of dye is mixed well with 2 ml of cold water and 30 ml of warm water are added Water (50 to 60 ° C) too; the dye dissolves in the process.

The dye solution is added to the liquor and 10 g of cotton tuvebe in this dye liquor kept moving constantly. The temperature of the dye liquor is increased to 85 bis within 30 minutes 90 ° C and continues to dye at this temperature for 60 minutes. The colored material is removed from the Dye liquor, removes the adhering liquor by wringing out, rinses the material for 5 to 10 minutes cold water and dries at 60 to 70 ° C.

Claims (1)

Palen tunes: I. Trisazo dyes of the formula H ₂ N OH wherein A = phenyl, optionally substituted by halogen, methyl, ethyl, methoxy, ethoxy, Nitro or sulfo, B = hydroxyphenyl, diaminophenyl optionally substituted by methyl or ethyl