DE2825727A1 - ANIONIC DISAZO COMPOUNDS, METHOD OF MANUFACTURING AND USE - Google Patents

Description

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SANDOZ-PATENT-GMBH

L ö r r a c h Case 150-4076

Anionic disazo compounds, process for preparation and use

The present invention includes anionic disazo compounds, processes for their production and their use as dyes. The invention relates to disazo compounds of the formula

N = N

in which the SO M group is in the m or p position to the azo group,

° M hydrogen or an equivalent of a colorless cation and R and R independently of one another are hydrogen, (1-4C) alkyl or

(1-4C) alkoxy
mean, as well as mixtures of the compounds of the formula I.

R resp. R in the meaning of alkyl is preferably methyl or Ethyl, especially for methyl.

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R resp. R in the meaning of alkoxy is preferably methoxy or ethoxy, especially for methoxy.

R is preferably R 'in the meaning of hydrogen or methoxy, especially for hydrogen.

R. preferably stands for R 'in the meaning of hydrogen or methyl or methoxy, especially for hydrogen.

Preference is given to compounds of the formula I in which R is R ¹ and R is R '; Particularly preferred are compounds of the formula I in which R and R are hydrogen.

The nature of the cation M of the sulfo group in compounds of the formula I is not a critical factor, but can mean any cation customary in the chemistry of anionic azo dyes, for example an alkali metal ion or an unsubstituted or substituted

tuted ammonium ion corresponding to the formula N (R), wherein each R is independently from each other hydrogen, (1-4C) alkyl or 2-, 3- or 4-hydroxy- (2-4C) alkyl means; known to be unstable cations such as tetraalkanolammonium ions are to be excluded. Examples of suitable cations are lithium, sodium, potassium, ammonium, mono-, Di-, tri- and tetramethylammonium, triethylammonium, mono-, di- and triethanolammonium and mono-, di- and triisopropanol ammonium. Preferred cations are the alkali metal ions, especially sodium, and also ammonium.

The compounds of formula I or mixtures thereof are prepared by the diazo compound from an amine of the formula

in which the SO "M - group is in the m- or p-position to the azo group, or mixtures thereof

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on p-tert. Butylphenol couples, expediently in an alkaline medium.

The compounds of the formula I obtained can be prepared according to known methods Methods are isolated from the reaction mixture. Usually the compounds of formula I fall depending on the reaction conditions in the form of their salts. If desired, a transfer to the free acid or a salt change can be carried out; the conversion into another salt form can also be carried out in a manner known per se take place.

The monoazoamino compounds of the formula used as starting material II are either known or they can be prepared analogously to a method known per se. The diazotization of an amine of the formula II is also carried out in a manner known per se.

The compounds of the formula I are and can be anionic dyes can be used for dyeing and printing any substrate that can be dyed with anionic dyes. Suitable substrates are, for example natural and synthetic polyamides, basic modified polyolefins or polyurethanes as well as leather. However, the dyes are used with particular advantage for dyeing and printing fiber material made from natural polyamides such as wool or silk and in particular of synthetic polyamides, preferably nylon, consists or contains these, with yellow to red tones of different shades Nuance can be achieved.

In particular, because of their good properties, the dyes according to the invention can be used in carpet dyeing, in conventional printing and carpet printing processes.
They are also well suited for the space dye process.

The compounds of the formula I or mixtures thereof can be used as such or can also be used in the form of liquid or solid preparations. Processing to stable liquid, for example concentrated

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aqueous or solid dye preparations can be based on well-known Manner, e.g. by dissolving in suitable solvents such as water, optionally with the addition of a customary auxiliary, for example a solubilizer such as urea, or then by grinding or granulating. Such preparations can, for example, according to the information French patents 1,572,030 or 1,581,900.

It is also possible to use the compounds in the form of cold-dispersible compounds To use preparations. For this purpose, the dyes are in the presence of one or more customary anionic dispersants and optionally further aids are subjected to mechanical comminution by means of dry or wet grinding with the dispersion medium water and optionally then dried by atomization. The preparations produced in this way are distributed when they are introduced into the cold Water again in finely dispersed form and is therefore easy to handle.

To achieve the same goal as with a cold dispersible preparation, In some cases, the addition of the dispersant can be dispensed with, as the dye itself (only mixed with ordinary Coupage agent) is soluble in cold water or at least dispersible in cold water.

The fiber material can be mixed with the dyes by any suitable method of the formula I or preparations thereof are colored, in particular by the padding process or exhaustion process, of which the latter is preferred because the compounds of formula I are neutral. For printing, and especially for carpet printing, the usual methods are applicable.

The dyes of the formula I are characterized by good solubility and a good build-up capacity, the dyeings and prints obtained with the dyes of the formula I or mixtures thereof show good all-round fastness properties, especially high lightfastness, rubfastness and good wetfastness

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such as washing, water or perspiration fastness. In addition, the dyestuffs of the formula I can be used to achieve opaque colorations with streaky nylon.

These good properties, combined with the same level of dyeing fastness, are also particularly useful in carpet printing.

The dyes of the formula I according to the invention also have the essentials Advantage that they can be easily combined with dyes that are similar due to their coloring properties, especially in trichromes; the high-quality colorations of the individual dyes are also retained for the combination colorations; in particular, these do not show any catalytic effects fading.

In the following examples, parts are parts by weight and percentages Weight percent; the temperatures are given in degrees Celsius.

example 1

27.7 parts of 4-amino-l, l ^f -azobenzene-4'-sulfonic acid are dissolved at 35-40 ° in 200 parts of water with the addition of 30% strength aqueous sodium hydroxide solution at a pH of 9-10 6.9 parts of sodium nitrite dissolved in 25 parts of water are added and the mixture is added dropwise over the course of 15 minutes at a temperature of 0-5 ° to an initial charge of 35 parts of 30% strength hydrochloric acid, 50 parts of water and 100 parts of ice.

15.2 parts of p-tert. Butylphenol are in 100 parts of acetone and 200 parts Water dissolved with 30% sodium hydroxide solution and cooled to 0-4 °. In the course of 30 minutes, the prepared according to the above procedure is left Add dropwise diazo suspension, by adding 10% sodium hydroxide solution the pH is kept at 8.5-9.0. The mixture is stirred for 1 hour, then the reaction mass is acidified and treated with sodium chloride salted out. The deposited dye is filtered off with

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Washed 10% saline and dried; he corresponds to the formula

NaO ₃ S

• N = N-

N = N

C (CH ₃ )

and colors wool and synthetic polyamides in pure yellow tones good lightfastness and good wetfastness.

Further dyes of the formula I can be prepared analogously to Example 1 are obtained in the form of the sodium salt and for which the variables R and R and the position of the in the following table Sulpho group and in the last column J the shade of the coloring on polyamide are indicated. The colorations obtained with these dyes show good lightfastness and good wetfastness.

Tabel

E.g.
No. ^R i ^R 2 Position of
SO Na group J yellow 2 H H 3 do. 3 OCH ₃ H 3 do. 4th do. H 4th orange-brown 5 do. CH ₃ 4th do. 6th do. do. 3 brownish red 7th do. OCH ₃ 4th do. 8th do. do. 3

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Dyeing prescription

In one made of 4000 parts of water, 10 parts of anhydrous sodium sulfate and 2 parts of the dyebath from Example 1 are introduced into 100 parts of pre-wetted nylon cloth (nylon 66) at 40 °.

The dye liquor is heated to boiling temperature in the course of 30 minutes, hold it at this temperature for 1 hour, add 4 parts of glacial acetic acid and stop the dyeing by heating for a further 30 minutes Boiling temperature. During the dyeing process, the evaporated water is continually replaced. The yellow-colored nylon cloth is then taken from the liquor and rinsed it with water and dry it. Wool can be dyed using the same procedure.

The dyeings have good lightfastness and good wetfastness.

In an analogous manner, with the dyes from Examples 2-8 or with Mixtures of the dyes from Examples 1-8 are colored.

Printing specification

Polyamide is printed with a printing paste of the following composition:

30 parts of the dye according to Example 1

50 parts of urea

50 parts of a solubilizer (e.g. thiodiethylene glycol) 300 parts of water

500 parts of a suitable thickener (e.g. based on of locust bean gum)

60 parts of an acid donor (e.g. Ammontartrate) 60 parts thiourea.

The printed textile material is steamed for 40 minutes at 102 ° (saturated steam), then rinsed cold, then washed for 5 minutes at 60 ° with a dilute solution of a commercially available detergent and again

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rinsed cold. A reddish-tinged yellow print of good light- and wet fastness properties.

In an analogous way, printing pastes can be used, which are part of the a dye of Examples 2-8 or mixtures of dyes of Examples 1-8.

3700 / LE / HB / AF

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Claims (7)

SANDOZ-PATENT-GMBH L ö r r a c h Case 150-4076 patent claims 1. Disazo compounds of the formula N = N SO ₃ M OH N = N c (CH ₃ ) wherein the SO M - group is in the m- or p-position to the azo group , M is hydrogen or an equivalent of a colorless cation and R and R independently of one another are hydrogen, (1-4C) alkyl or (1-4C) alkoxy
mean, as well as mixtures of the compounds of the formula 2. Compounds according to claim 1, wherein R and R are hydrogen. 3. Process for the preparation of compounds of the formula I according to claim 1 or mixtures thereof, characterized in that the dxazo compound from an amine of the formula 809882/0723 Case 150-4076 N = N in which the SO M group is in the m- or p-position to the azo group,
or mixtures thereof on p-tert. Butylphenol couples. 4. Process for dyeing or printing with anionic dyes dyeable substrates, characterized in that one is a compound of formula I or mixtures thereof according to claim 1 or 2 is used. 5. The method according to claim 4, characterized in that as Substrate uses natural or synthetic polyamides, leather, basic modified polyolefins or polyurethanes. 6. The method according to claim 5, characterized in that as Substrate uses fiber material, which consists of natural or synthetic polyamides such as wool, silk and especially nylon or contains them. 7. The substrates dyed or printed according to claims 4-6. 809882/0723