SU451254A3 - Method for preparing active chlorotriazine azo dye - Google Patents

Description

The invention relates to the preparation of novel active dyes, in particular, to a method for producing a chlorotriazine azo dye containing a phenylenediimodisulfonic acid residue, which can be used to dye cellulose textile materials.

A known method of producing an active chlorotriazine azo dye containing a phenylenediamine sulfonate residue.

The method consists in the condensation of cyanuric chloride with diamip and a dye compound.

The disadvantage of dyes obtained by a known method is the low fixation of dyes on cellulosic fibers and satisfactory durability with respect to wet treatments.

To eliminate these drawbacks, a method has been proposed for the preparation of a new active chlorotriazine azo dye, in the synthesis of which a new raw material, phenylene diamino disulfonic acid, is used.

The proposed new dye has the general formula DN-C0-NH

B 4 / N

N

where R is hydrogen or an alkyl group;

D is the residue (1: 1) of the metal complex of the amino nitrogen compound;

X - 2 - S is a triazinyl ring containing a chlorine or bromine atom at the fourth hydrocarbon atom, a substituted or unsubstituted amino group at the sixth hydrocarbon atom.

The method consists in the fact that the dye compound of the indicated formula, where X is a 4,6-dichloroyl dibromo-5-triazin-2-yl group, is treated with ammonia or an amine, followed by isolation of the target product in a known manner.

The original dye compound is prepared in a known manner, for example by condensation

Phenylenediamine disulfonovye

Compounds of the formula DNHR

4. 4- (4-Sulfophenylazo) -2-sulfophenylazo-1-neftylamine-6-sulfonic acid

6-Uroido - 2- (5-aminophenylazo) -1-naphtol-2-disulfr acid

b-Amin-1-oxide-2, 2-azonaphthalene-I, 3. 5, 5-tetrasulfonic acid

Also

8-Acetylamine-2- (3-aminophenylazo) -1-naphtol-3, 4, 6-trisulfonic acid

Also

4-Nitro-4- (4-methylaminophenyl azo) -stilben-2,2-disulfonic acid

1, 2-Diaminobenzene4-Nitro-4- (4-methylaminophenyl-2, 5-disulfonic acid azo) -stilbene-2,2-disulfonic acid

I, 3-Diaminobenzene4-Nitro-4- (4-methylaminophenyl-4, C-disulfonic acid azo) -stilbene-2,2-disulfonic acid

Also

Also

b-Amin-2- (phenylazo) .1-naphthol-2, 3-disulfonic acid

Also

o- (Methylamine.2-4-methoxyphenyl1, 4-diaminobenzazole) -1-naphthol-2, 3-disulfonic acid -2, 5-disulfonic acid

Also

1, 3-diaminobenzene-4, 6-di sul l foxis lot

Table

Amines used

in the last stage

acids

condensation

2, 4-Dichloro-6- (and -sulfoaniline) -symm. triazine

2, 4-Dichloro-6-amine-symm. triazine

Also

2, 4-dichloro-6-methoxy-symm. traizin

2, 4-dichloro-6- (l-sulfoaniline) -stim. triazine

2, 4-Dichloro-6-aniline-simm. traizin

2, 4-Dichloro-6-methoxy-sym. triazine

2, 4-Dichloro-6- (3, 5-di sulfaniline - symmetry. Triaai

2, 4-Dichloro-6-amine-symm. triazine

2, 4-Dichloro-6- (3, 6. 8-trsulfonapht-1-ylamine) -sym triazine

2, 4-Dichloro-6- (l "-sulfoaniline) -stim. triazine

2, 4-Dichloro-6-aniline-sim triazine

2, 4-Dichloro-6- (4-sulfoaniline) -symm. triazine

2, 4-Dichloro-6-amine-symm. triazine

2, 4-Dichloro-6- (3. 6. 8-trsulfonapht-1-yl-amine) -sym triazine

2, 3-Dichloroquinonsalin-6carbonyl chloride

Carbisulphate

2, 4, 6-Trichloropyrimidine

2, 4-Dichloropyrimidine-5-and-carbonyl chloride

2, 4-Dichloro-6-aniline-sim triazine

2, 4-Dichloro-6- (l-sulfoaniline) -symm. triazine

2, 4-Dichloro-6-amine-symm. triazine

2, 4-dichloro-6-methoxy-symm. triazine

Also

Phenylenediamine disulfonovye

 Compounds of the formula DNHR

1, 3-Diaminobenzene-4,

o-Methylamine-2- (4-methoxyphenyl 6-disulfonic acid azo) -1-naphthol-2,3-disulfonic acid

Also

Also

I, Z-Diaminobenzene-4,

8-Amin-2- (phenylazo) -1-naphthol-2, b-disulfonic acid 3, 6-trisulfonic acid

That W9

Also

8-AMIN-1-OXI-2, 2-azonaphthalene-G, 3, 6-trisulfonic acid

That w§

I, 4-diaminobenzene-2, 5-disulfonic acid

Also

8-Amin-1-hydroxy-2, 2-azonaphthalene-G, 3, 6-trisulfonic acid

Also

8-Amin-2-phenylazo-7- (5-aminophenylazo) -1-naphthol-2, 2, 3, 5, 6-penta asu lfokis lot

8-Amin-2-phenylazo-7- (5-aminophenylazo) -1-naphthol-2, 2, 3, 5, 6-pentasulfonic acid

Also

1, 3-Diaminobenzene-4, 6-disulfonic acid

8-Aniline-2- (4-aminophenylazo) -1Also-naphthol-3, 3, 6-trisulfonic acid

Also

1, 4-diaminobenzene-2, 5-disulfonic acid

8-Aniline-2- (4-aminophenylazo) -1Also-naphthol-3, 3, 6-trisulfonic acid

P ro d d l o n s

Amines used

in the last stage of the acid

condensation

2, 4-Dichloro-6- (2-methyl-5. Sulfoaniline) -symm. triazine

2, 4-Dichloro-6-amine-symm. triazine

2, 4-Dichloro-6-ethoxy-Simm. simm triazine

2, 6-Dichloro-6.amin-simm. triazine

2, 4-Dichloro-6- (3, 5-lisulfoaniline) tsymm. triazine

Also

2. 4-Dichloro.6-methoxy.symmetry triazine

2. 4-Dichloro-b-amine-simm. traizin

Also

2, 4-Dichloro-6-methoxy-simm triazine

2, 4-Dichloro-b-aniline-simm. triazine

2, 3-Dichloroquinoxaline-6-carbonyl chloride

Carbonyl sulfate

2, 4, 6-Trichloropyrimidine

2, 4-Dichloropyrimidine-5-carbonyl chloride

2, 4-Dichloro-6-aniline-simm. triazine

2, 4-Dichloro-6-parasulfoaniline-simm. triazine

2, 4-Dichloro-6-methoxy-simm triazine

2, 4-Dichloro-6- (2-methyl-5-sulfonaniline) -symm. triazine

2, 4-Dichloro-6- (methasulfoaniline) -symm. triazine

2, 4-Dichloro-6-amino-symm. triazine

2, 4-Dichloro-6-methoxy-simm triazine

Also

Dark Goal2. 4-dichloro-6-aniline-simm. triazine fight

Phenylenediamine disulfonovye

Compounds of the formula DNHR acid

8-Aniline-2- (4-aminophenylazo) -1-naphtol-3, 3, 6-trisulfonic acid

Also

2- (Phenylazophenylazo) -6-amine-1-naphtol-3, 4 Disulfonic acids

Also

1-amine-2, 7- (is- (4-amino-4-phenylazo) -8-naphthol-2, 2, 3, 6-tetrasulfonic acid

Also

4-Amin-2-methyl-4- (phenylazo) -azobenzene-2, 4 disulfonic acid

Also

1, 4-diaminobenzene2, 5-disulfonic acid

Also

4-Nitro-4- (4-amine-2-methylfe-j nilazo) -stilben-2, 2-disulfonic acid I

Also

1,3-Diaminedibenzene-4, 6-disulfonic acid

Also

4, 4-5b ;-( 1 -Oxy-3. 6-disul. Pho-8-amino-naphth-2 -ilazo) -stilben-2, 2-disulfonic acid

Also

Continuation

Amines used

in the last stage

condensation

2, 4-Dichloro-6 - ("- sulfoaniline) -symm. triazine

2, 4-Dichloro-b-aminosymm, triazine

Also

Cyanuric chloride

2. 4. Dichloro-b- (l-sulfo. Aniline) -symm. triazine

2. 4-Dichloro-b- (3, 5-di. Sulfoaniline) -symm, triazine

Also

2, 4-Dichloro-b- (l-sulfoaniline) -symm. triazine

Also

Cyanuric chloride

2, 4. Dichloro-b- (2, 5-disulfonaniline) -symm. trnazi

2, 4-dichloro-6-methoxy-symm. triazine

Also

2, 4-Dichloro-6- (3, 5-disulfonaniline) -symm. triazine

I I

I 2, 4-Dichloro-6-amn-simm. 1 triazine I

Also,

Yellow

2, 4-Dichloro-6- (3. 5-disulfonaniline) -symm. triazine,

2, 4-dichloro-6- (l1-sulfoaniline) -stim. triazine;

Same

Cyanuric chloride

2, 4-dichloro-6-methoxy-symm. trnazine

2, 4-Dichloro-6-aniline-simm; triazine

i

Bright same blue

Also

Cyanuric chloride

Prod toe and e

cyanuric chloride with a metal complex of amino nitrogen compounds and phenylenediaminodisulfonic acid.

The treatment of the starting dye compound with ammonia or an amine is carried out in an aqueous medium at a pH of 5-7, preferably at 30-50 ° C in the presence of an coupling agent.

Introduction to active grouping dye

N

-C-Sh 1 11 Ny

I L

by using phenylenediaminodisulfonic acid, it provides a high degree of fixation and improved color fastness to wet treatments.

In this way you can get a wide range of color shades of dyes - from blue to dark blue and magenta.

Example. A solution of 8.0 weight. including tetrasubstituted sodium salt of the copper complex of 8-amino-1,1-Dioxy - 2,2 - azonaphthalene-3,4-6,8 quadruple substituted sulfonic acid in 125 weight. water added to the suspension 1.85 weight. including acid chloride cyanuric acid and 14 wt. including acetone in I2 weight. including water at O-5 ° C, maintaining the pH of the mixture 5-7 by adding 10% aqueous solution of carbonate

on three . At the end of the condensation, a solution of 4.0 wt. including disubstituted sodium salt. 1,4-diaminobenzene-2,5-disulfonic acid in 30 weight. including water and the temperature is raised to 35-40 ° C, maintaining the pH

4.5-5.0 by the gradual addition of a 10% aqueous solution of sodium carbonate. At the end of the condensation, to the pH of the aminomonazoxide dye at 0-5 ° C, maintaining the pH at 5-7 with the addition of a 10% aqueous solution of sodium carbonate, 2.0 weight% is added. including acid chloride cyanuric acid in 15 wt. including acetone. At the end of the condensation, a solution of 3.0 wt. including aniline in 10 wt. including acetone and the temperature is raised to 35-40 ° C, maintaining the pH at 5-7 by adding 10% sodium carbonate solution. After condensation, the dye is precipitated by the addition of sodium chloride, filtered and solid. The dye contains 2 chlorine atoms per azogrunpa at

applying it to the pulp material in

in the presence of an acid binding agent,

a light blue shade with good results

resistant to light and wet treatments.

Similarly to the above example, the dyes obtained in the table.

Subject invention

The method of obtaining active chlorotriazine azo dye of the general formula

ct

where R is hydrogen or an alkyl group;

D is a residue of 1: 1-metal complex of the amino nitrogen compound of the formula DNHR;

X-2-S is a triazinyl ring containing an atom or bromine at the fourth carbon atom and an unsubstituted or substituted amino group at the sixth carbon atom, characterized in that, in order to obtain dyes with increased fixation on cellulosic fibers and with increased strength to wet treatments, a dye compound of the indicated formula, where X is a 4,6-dichloro- or dibromo-S-triazin-2-yl group is treated with ammonia or an amine, followed by isolation of the target product in a known manner.