DE1644086C3 - Dispersion monoazo dyes - Google Patents

Description

lq- \

wherein W is a hydrogen, chlorine or bromine atom, nitro or cyano, Z is a hydrogen, chlorine or bromine atom, X is a hydrogen atom, methyl or methoxy, Y is acetylamino or propionylamino, R is lower alkyl with 1 to 4 carbon atoms or benzyl, q 1 or 2 and A, optionally substituted by nitro, cyano, methyl, ethoxycarbonyl, p-chlorophenyl or p-nitrophenyl, thiazolyl optionally substituted by nitro, cyano or methoxy, optionally substituted 1,3 by nitro, methyl, methoxy or phenyl , 4- or 1,3,5-thiadiazolyl or 3-nitro-5-acetylthienyl-2.

2. disperse dyes according to claim 1, characterized by the general formula

^30th

CH ₂ CH ₂ OR

CH ₂ CH ₂ CN

wherein R, W, X, Y and Z have the meaning given in claim 1. 3. disperse dyes according to claim 1 and 2,

CHXH ₁ -OR

CH, CH, CN

characterized by the general formula Z

O ₂ N ^ (^> - N = N-B

W wherein B is a radical of the formula

CH ₂ CH ₇ OCH,

-N

CHXHXN

NHCOCH ₃

or

? ^ch3 ch ₂ ch ₂ och ₃

n '

CH ₂ CH ₂ CN

NHCOCH ₃

and W and Z have the meaning given in claim 1.

The invention relates to valuable, water-insoluble dispersion monoazo dyes of the general formula

(A) ₂ -,

O, N

W / _rl CH ₂ CH ₂ -OR

wherein W is a hydrogen, chlorine or bromine atom, nitro or cyano, Z is a hydrogen, chlorine or bromine atom, X is a hydrogen atom, methyl or methoxy, Y is acetylamino or propionylamino, R is lower alkyl with 1 to 4 carbon atoms or benzyl, q 1 or 2 and A, optionally substituted by nitro, cyano, methyl, ethoxycarbonyl, p-chlorophenyl or p-nitrophenyl, thiazolyl optionally substituted by nitro, cyano or methoxy, optionally substituted 1,3 by nitro, methyl, methoxy or phenyl , 4- or 1,3,5-thiadiazolyl or 3-nitro-5-acetylthienyl-2.

_{CH 2} CH ₂ CN is added to the dyes according to the invention

if you have a diazotized amine corresponding to the above formula with an azo component the general formula

CH ₂ CH ₂ -OR

CHXHXN

couples, in which R, X and Y have the meanings given above.

The diazo component used is preferably monocyclic aromatic amines of the formula

NH,

wherein W is hydrogen, chlorine or bromine, nitro or cyano and Z is hydrogen, chlorine or Bromine atom is.

Of the heterocyclic amines mentioned below, particularly suitable diazo components are the aminothiazoles or aminobenzothiazoles mentioned.

The following amines are examples:

l-amino-4-nitrobenzene,

1-amino-l-chloro- ^ nitrobenzene, 1-amino-2,6-dichloro] or-4-nitrobenzene.

l-amino-2-cyano-4-nitrobenzene, 1-amino-2,4-dinitrobenzene,

l-amino ^^ dinitro-o-chlorobenzene, 1-amino-2,4-dinitro-6-bromobenzene, 2-amino-6-cyano-benzothiazole, 2-amino-6-nitro-benzothiazole,

2-amino-6-methoxy-benzothiazole, 2-amino-5-nitrothiazole,

2-aniino-5-cyanothiazole,

2-Amino-5-carbethoxythiazole, 2-Amino-4-methyl-5-cyanothiazole, 2-amino-4,5-dicyanthiazole,

2-Amino-5-nitro-thia (l) -diazol- (3,4), 2-Amino-4-phenyl-thia (1) -diazol- (3,5), 2-Amino-4-methyl-thia (1) -diazole- (3.5), 2-amino-4-methoxy-thia (1) -diazole- (3.5).

As azo components come, preferably amines of the general formula

CH, CH, O-R

CH, CH, CN

into consideration, in which X, Y and R have the meanings given above.

The following azo components may be mentioned as examples:

CH ₂ CH ₂ OCH ₃

CH ₂ CH ₂ CN

NHCOCH ₃
OCH ₃

CH ₂ CH ₂ OCH ₃

CH ₂ CH ₂ CN NHCOCH ₃

The azo components mentioned can be obtained by known processes, for example by alkylation of the monocyanethylanilines with the corresponding 2-alkyl-oxyethanol-benzenesulfoesters.

The coupling can also be carried out in a manner known per se, for. B. in neutral to acidic Mitlei, optionally in the presence of sodium acetate or similar, the coupling rate influencing buffer substances or catalysts, such as. B. pyridine, respectively. its salts, are made.
After the coupling reaction has taken place, the

ίο dyes formed from the coupling mixture, z. B. separated by filtration, since they are practically insoluble in water.

Instead of a single diazo component, it is also possible to use a mixture of two or more of the stated diazo components and, instead of a single azo component, a mixture of two or more of the stated azo components.
The monoazo dyes according to the invention, after being converted into a finely dispersed form, are excellently suited for dyeing synthetic fibers, in particular aromatic polyesters. Deep, orange to blue dyeings of good lightfastness and sublimation fastness are obtained.

Compared to the dyes described in British Patent 8 13 906, which instead an N-alkoxyalkyl have an N-acylox> alkyl group, The dyes obtainable according to the invention are distinguished by a lower alkali sensitivity wedge out.

Compared to the dyes mentioned in BE-PS 6 60452, the dyes according to the invention show a significantly better drawability.
For dyeing, the dyes according to the invention are expediently used in finely divided form and dyeing is done with the addition of dispersants, such as soap, sulphite cellulose waste liquor or synthetic detergents, or a combination of various wetting and dispersing agents. As a rule, it is expedient to convert the dyes into a dye preparation before dyeing which contains a dispersant and finely divided dye in such a form that a fine dispersion is formed when the dye preparations are diluted with water. Such dye preparations can be used in a known manner, for. B. by precipitating the dye from sulfuric acid and grinding the resulting slurry with sulphite liquor, optionally also by grinding the dye in highly effective grinding devices in dry or wet form with or without the addition of dispersants during the grinding process.

Thanks to their alkali fastness, the dyes according to the invention are particularly suitable for post-dyeing the so-called thermosetting process, after which the fabric to be dyed with an aqueous dispersion of the dye, which advantageously 1 to 50% urea and a thickener, in particular Sodium alginate, preferably impregnated at temperatures not exceeding 60 ° C and as usual is squeezed. Expediently, one squeezes off so that the impregnated goods are 50 to 100% of theirs Retains initial weight of dye liquid.

To fix the dye, the fabric impregnated in this way is expediently dried after prior drying, e.g. B. in a well air stream, to temperatures of over 100 ⁰ C, for example between 180 and 220 ° C, heated.

The heat setting process just mentioned is of particular interest for dyeing blended fabrics made of polyester fibers and cellulose fibers, especially cotton. In this case, the padding liquid contains in addition to the dyes according to the invention, dyes suitable for dyeing cotton, especially vat suffe, or reactive dyes, d. H. Dyes that can be fixed on the cellulose fiber by forming a chemical bond are, for example dyes, containing a chlorotriazine or chlordiazine radical. In the latter case The padding solution proves to be useful an acid-binding agent, for example an alkali carbonate or alkali phosphate, alkali borate or perborate or their mixtures to be added. When using vat dyes there is a treatment of the padded fabric after heat treatment with an aqueous alkaline solution in the Vat dyeing usual reducing agent necessary. The dyeings obtained are expediently an aftertreatment subjected, for example, by heating with an aqueous solution of an ion-free Detergent.

Thanks to their good reserve of wool, the dyes according to the invention are also excellently suited for dyeing blended fabrics made of polyester fibers and wool.

The dyes can also be applied by printing. Used for this purpose one z. B. a printing ink that, in addition to the auxiliaries commonly used in printing, such as wetting agents and thickeners, the finely dispersed dye, optionally in a mixture with one of the abovementioned Cotton dyes, optionally in the presence of urea and / or an acid-binding agent.

In the following examples, the parts mean. unless otherwise stated, parts by weight, the percentages by weight and the temperatures are given in degrees Celsius.

example 1

19.75 parts of 1-amino-Z.ö-dichloro- ^ nitrobenzene become portion-wise in 60 parts conc. Sulfuric acid in which 6.9 parts of sodium nitrite were dissolved.

ίο registered. Obtained by pouring onto 400 parts of ice you get a clear, yellow solution.

The diazo solution thus obtained is allowed to flow into a solution which contains 29.1 parts of 1-methoxy-2 - (N - cyanoethyl - N - methoxyethyl) -amino-4-propionylaminobenzene Contains glacial acetic acid in 100 parts by volume. The precipitated with the addition of sodium acetate Dye dyes acetate silk, nylon, triacetai and polyester in purple tones.

Example 2

5 parts of 2-aminothiazole are concentrated in portions in 30 parts. Sulfuric acid, in which 3.5 parts Sodium nitrite were dissolved, entered. Pouring onto 200 parts of ice produces a clear yellow

2s solution.

The diazo solution thus obtained is left in a solution of 13.0 parts of 3-acetamino-N-cyanoethyl-N-methoxyethyl-aniline flow in 300 parts by volume of 2N sulfuric acid. By adding saturated sodium acetate solution the dye is precipitated, which acetate silk. Color nylon, triacetate and terylene in orange-red tones.

In an analogous manner, two further dyes were made from those listed in the table below

λ? Components 1 and II get which polyester fibers color in the shades listed in column III.

St.

2-amino-5-nitrothiazole

C ₂ H ₄ OCH ₃

blue

2-amino-6-cyanobenzothiazole

NHCOCH ₃ - ¹ ^ '

C ₂ H ₄ OCH ₃

-N

\
NHCOCH ₃ ^C21

blue red

Claims (1)

Claims: 1. Dispersion monoazo dyes of the general form! Z \ X (A) ₂ -, O ₇ N N = N