DE1619357B - Use of highly concentrated, stable stock solutions containing 1 2 metal complex dyes for the preparation of dye baths or printing pastes - Google Patents

Description

1 2

Obtainable for dyeing or printing nitrogen padding liquor, as the high concentrations

containing fiber material, e.g. B. of wool, silk or trations strong agglomeration effects can occur.

Synthetic polyamide fibers are primarily used to produce uneven and very spotty prints

anionic dyes used. Thereby one obtains and stains lead. The one with the dye

especially light-, wash- and perspiration-fast dyeings, 5 introduced large amounts of dispersants

if you have sulfonic acid group-free 1: 2 chromium or also interfere with the fixation of the dyes on the

Cobalt complexes used by azo dyes. Ub fiber, especially in steaming and thermosol processes.

Licherweise these dyes are in the form of fine. Attempts have also been made to solve the problem

ground powders containing thickening agent supplied, when dissolving large amounts of dye powder thereby

dissolved or dispersed for dyeing in the dyebath to avoid using liquid instead of powder

Need to become. Apart from the unpleasant, dye preparations used. For the production

due to the powder form caused dust generation of such preparations are water, dye and

Intensive coloring dyes and the risk of dispersing agents to be used particularly carefully to form a paste

baking the dye powder, prepare the grinding until the desired degree of fineness is achieved

dissolve or the dispersion of the solid dyes in the 15 is and you get a thin, pourable paste.

Dyebath not minor difficulties, since they can mostly do this, however, only very difficult in water

are only insufficiently soluble in water. soluble dyes are used.

Light to medium shades are made from a long liquor The dye dispersions obtainable in this way can be colored, so there are usually no problems with the preparation of padding liquors, especially since cooking printing pastes are usually easier to handle, but they have temperatures or temperatures above 100 ⁰ C works. various serious drawbacks. This is how it is. If, on the other hand, deep shades of color, especially marine shades are not possible, the dye content of the pastes beyond blue and black, it is often possible to increase the content of the pastes beyond blue and black, even at boiling temperatures of 15 to 20%, if they do not remain liquid The sulfonic acid used should, as at higher concentrations, thicken group-free metal complex dyes completely in the suspensions and also dissolve thixotropic effects. You can then step into undissolved form, which deposit form on the material to be dyed for the handling of the preparations, and poor friction is extremely obstructive. Creating authenticity is particularly annoying. Particular difficulties in the sinking of the dye particles to the bottom arise when the liquor flows through the textile of the vessels during dyeing, which occurs especially during prolonged storage, z. B. when dyeing cross-30 and can lead to the formation of a solid sediment, bobbins or fabrics on a piece of tree dye can be done by shaking the vessels or by apparatus. In the process, undissolved dye particles can no longer be homogeneously distributed by stirring. The danger of the formation of a sediment, which is filtered off and deposited on the textile material, exists; a particularly bad rubbing fastness is the special one when due to some external consequence. Particularly great difficulties arise when storing the liquid dispersions when for continuous dyeing processes and at higher temperatures. Water-based suspen textile printing, relatively high dye concentrations, anions are also sensitive to the cold because they have to be turned. Unless the water can freeze and you then have to thaw a padding liquor with particular care due to the remaining undissolved dyestuff, or a printing paste that is sufficiently fine to ensure that no agglomeration occurs and that fine distribution is achieved, the result is restless and speckled division is disturbed.
Dyeings or prints. It has now been found that one can avoid

You can now achieve a good fine distribution of the difficulties outlined textile material made of turned sparingly soluble metal complex dye powder nitrogen-containing fibers with 1: 2 metal complex by adding them together with 45 dye-containing dyebaths or pressure dispersants, e.g. B. reaction products of pastes can be colored or printed if, for formaldehyde with naphthalenesulfonic acid or phenol preparation of the dyebaths or printing pastes, high sulfonic acid is ground to an aqueous paste and concentrated, stable, with water in every ratio closing to a fine, largely homogeneous one Uses miscible stock solutions that dries sulfonic acid powder. However, the fineness of the group-free 1: 2 chromium or cobalt complexes is limited by adjustable powders, and it is especially in the case of azo dyes in oxygen-containing solvents that are still slightly soluble in water in dyes that are miscible in any ratio contain ability, extremely difficult to achieve a definite and specific metal-free dye in the specified degree of fineness by metallizing the specific metal-free dyes required especially for continuous dyeing processes, since 55 solvents have already been obtained during grinding,
The paste of water, dye and dispersant It was particularly surprising and advantageous-recrystallization can occur, which counteracts the necessary adhesion and economic that the metal complex formation disperses. from dyes and metal compounds directly

Such finely divided powders also contain considerable amounts of dispersants known in principle in these solvents. B. Black 1: 2 metal complex dyes obtained after filtering, or navy blue, obtained on a material or centrifugation can be used directly,
should that only a very limited amount of the padding liquor can take up according to the invention for the preparation of the dye. This is e.g. B. stock solutions used in densely packed baths are the case without woven fabrics made of polyamide filament fibers. precipitation of the dye in any proportion with water

Often it is also not possible to mix them with the required, regardless of whether you have them with water

large amounts of dye at all a stable diluted or poured into water.

3 4

One can even use those aqueous solutions that contain 10 to 20 g of dye per liter, which are not used for complex formation. B. boil the trivalent or hexavalent chromium long with stirring without the dye or the bivalent or trivalent cobalt. The leg is precipitated in any appreciable amount. The basic conditions of the metallization must be chosen so that the solutions have a low viscosity and are also 5, so that the 1: 2 complexes are formed, even at temperatures well below freezing. In the same way, an increase in the initially with aids and the temperature setting for z. B. 40 to 60 ⁰ C is not harmful, the required pH value of the necessary acids rather the stability of the solutions or buffer salts will circulate and then gives the color still improved; the increase in temperature therefore has to do with substance in the form of the stock solution. For the setting, the opposite effect as in the case of the previously mentioned pH value in each case has been found to have dispersant-containing suspensions. organic acids and bases, such as. B. acetic acid or

Triethanolamine, suitable for the preparation of the stock solutions, has proven to be the best.

Water miscible in all proportions Solvents that can be used for dyeing with sulfone

are for example alcohols, in particular more- 15 acid group-free 1: 2 metal complex dyes.

valuable alcohols with neighboring hydroxyl groups are used and known agents

as well as their esters and ethers, ethanolamines and are used, z. B. addition products of

open-chain or cyclic carboxamides or ethylene oxide with aliphatic alcohols or alkyl

Mixtures of such compounds. The alcohols phenols and their half esters with sulfuric acid,

Like their esters and ethers, they can also add 20 products of the addition of ethylene oxide to aliphatic

by one or more carboxylic acid, aldehyde or amines, sulfation products of castor oil, the oil

Be substituted by ketone groups. In particular, acids and their amides with aliphatic amines,

for example the following compounds are mentioned: alkylbenzenesulfonic acids or alkylnaphthalene sulfonic acids

Ethylene glycol, diethylene glycol, 1,2-propylene glycol, acids. Mixtures of the

Ethylene glycol mono-n-butyl ether, diethylene glycol 25 of the aforementioned auxiliaries, especially those used in

mono-n-butyl ether, diethylene glycol monomethyl ether, boiling temperature have no cloud point. This

Glycol monoacetate, glycerol, glycol aldehyde, glycol agents and mixtures thereof are known and are in the

acid, ethylene carbonate, propylene carbonate, butyrolac literature widely described,

clay, pyrrolidone-2, N-methylpyrrolidone, dimethyl- Since in practically all cases these are surfaces

formamide, tetrahydrofuran, dioxane and dimethyl 30 active compounds, they often tend to be very strong

sulfoxide. to foam formation, which is very important when coloring the bath

The stability of the stock solutions or which has a disruptive effect. It has now been found that after

dyebaths made from it are particularly large; the addition of the above-described dyes

if, as a solvent, adducts from holding stock solutions have a clear foaming

1 to 5, preferably 2 to 4 mol of ethylene oxide at 35 attenuation occurs when deep shades, z. B. Black

aliphatic alcohols with 2 to 6 carbon atoms, or navy blue, are colored and accordingly

preferably of propanols or butanols. a lot of dye is used. When dyeing light-

Addition products of ethylene oxide to alcohols ren color shades and with long liquor ratios with more than 6 carbon atoms or alkyl the foam suppression is of course less pronounced, Phenols can be used advantageously as additives 40 In the course of the coloration, the dyes are very weak However, the fiber must then be applied accordingly, and the result is an excellent one Number of carbon atoms more ethylene nete bath exhaustion, especially with deep oxide molecules be attached so that the connections are tinted and is very important with black. Since during are water soluble. For example, in the case of nonyl staining, there are no deposits or precipitates phenol requires at least 6 to 7 moles of ethylene oxide 45 occur, the dyeings have a very good friction, with coconut fatty alcohols or decanols with authenticity. This is especially true in apparatus dyeing branched carbon chain about 8 moles of ethylene- very important, in which the dye liquor is the material oxide. Flows through when using additive products.

With a high carbon number, it is convenient to use them in continuous dyeing

together with salts of alkylbenzenesulfonic acids 50 from stock solutions the preparation of the padding liquors

with organic amines, especially mono-, di- extraordinarily. The often time-consuming loosening is no longer necessary

and add triethanolamine, so that a good or dispersing large amounts of dye powder, there

Dissolve or mix when pouring into water the stock solutions only in the, if necessary

is achieved. Also half esters of glycols, digly already mixed with auxiliaries and thickeners

Kolen, triglycols or tetraglycols or mono- 55 aqueous solution must be poured in or stirred in. this

Ester of glycerol, tetrites, pentites or hexites is particularly advantageous if, for example

with aliphatic carboxylic acids with 2 to 5 carbon floor coverings made of polyamide fiber material, such as tufting

Atoms have proven particularly useful as additives. carpets or needle felt material, in large quantities

The sulfonic acid groups come as dyes - must be colored continuously and therefore pro

free chromium or cobalt 1: 2 complexes of 60 batches of several cubic meters of padding liquor are required

ο, ο'-dioxy, o-oxy-o'-carboxy and o-oxy-o'-amino.

azo dyes into consideration. You can use them in the form. Further advantages result from the fact that the color

Their free complex acids or their alkali or substances in solutions prepared in this way are essential

Use ammonium salts, e.g. B. as a diethanoi- show better pulling power. With unchanged

ammonium salts. 65 steaming times, the dyes are not just based on the

In addition, synthetic polyamide fibers or wool can also be used better as starting products

o-Oxy-o'-alkoxy-azo dyes are used, thereby fixed, but also on the hard used:

the metalization, the alkoxy group is dealkylated. fibers that form the base fabric for tufted carpets and

5 6

Form needle felt paint. This is especially true at the cooking temperature. The direction of circulation is

Coloring of deep tones is important. In parallel to the so the fleet changed several times,

Achieved better fixation of the dyes results The dye bath is then clear and only dark

a purple color compared to dyeings with powder dyes. By adding 1 part of acetic acid

significant improvement in the fastness to rubbing of the dye 5 it can still be exhausted, but this has

exercises that do not affect the achievable color depth, especially in the case of floor coverings.

important is. lent influence more. You get a deep black,

The flake, which is rub-resistant when using powder dyes, has excellent light,

difficulties in continuous dyeing with rubbing and wet fastness,

when dyeing difficult-to-adjust shades, ίο.

like beige, olive green, gray or light brown, can be example

by using stock solutions after the 30 parts of aqueous cobalt hydroxide paste, which by

avoid new method. So far this has resulted from the cases of 26 parts of cobalt (II) chloride with 20 parts

Necessity to use a combination of powdery 50% sodium hydroxide solution in 400 parts of water and other

Yellow, orange, red and blue dyes made for closing suction are used in

To use position of the dyebaths, often a mixture of 110 parts and dimethylformamide

The dyeings have a calm appearance because the 110 parts of diethylene glycol mono-butyl ether are

Not wearing the correct mixture of dye particles. Then you are at 8O ⁰ C 61.8 parts of

Monoazo dyes from diazotized! l-amino-2-oxy-

- which is particularly noticeable in light shades 20 4-nitrobenzene and ß-naphthol added and continued

makes - as is achieved by the use of 8 parts of S0 ° / ₀ sodium hydroxide solution and the mixture is stirred at 1 hour

Dye solutions have an absolutely homogeneous distribution at 100 ^° C. After cooling and filtering, one obtains

the dyes in the padding liquor and thus a solution that is stable even at low temperatures,

the fiber surface, so that perfectly level and which can be diluted with water without

calm colorations arise which show no flaccidity »5 precipitates,

exhibit. 5 parts of the solution obtained in this way are in a

It was also observed that in the dyeing winch to 100 parts of knitted fabric made of texturized with dissolved 1: 2 metal complex dyes purer polyamide 6,6 fibers in 3000 parts of water at 6O ⁰ C and clearer shades can be achieved than in the case and 1 part of Triethanolamine salt of sulfur using dispersed powder dyes. This acid half-ester of an addition product of 80 mols effect is likely to be related to the fact that the ethylene oxide is added to 1 mol of stearyl alcohol. The dyestuff powders contained adjusting or dispersing dye liquor will contain medium colored constituents for boiling within 30 minutes, which are often brought and kept at this temperature for 1 hour. Cause yellowing of the material to be dyed and, in addition, a bluish violet coloration with browning when exposed to light is obtained. Since metal components have excellent rub, wash and light fastness, plex dyes are generally not very brilliant. ·, *
Any improvement in this example is 3
Particularly valuable. 64.4 parts of the monoazo from diazotized

The information on parts and percentages in the post-2-aminobenzoic acid and l-phenyl-3-methyIpyrazo-

The following examples are based on weight. 40 ion-5 and 32 parts of sodium dichromate are used

100 ° C in a mixture of 80 parts of dimethylformamide

Example 1 ^and 80 parts of diethylene glycol mono-n-butyl ether added and then ^{stirred at 110 ° C. for 1} hour.

30.9 parts of the monoazo from diazotized! After the separation of minor precipitates

l-Amino-2-oxy-4-nitrobenzene and ^ -naphthol, 45 are obtained even at low temperatures

30.9 parts of the monoazo dyestuff from diazotized, resistant thin-

l-Amino-2-oxy-5-nitrobenzene and / 8-naphthol and liquid solution.

32 parts of sodium bichromate be at 100 ⁰ C in 30 parts of it with 20 parts zueammen

a mixture of 90 parts of dimethylformamide and the sodium salt of the terminal sulfated plant

90 parts of diethylene glycol mono-n-butyl ether incorporated 5 ° approximately product of 2MoI ethylene oxide to nonyl

wear and then ^{stirred at 110 0} C for 1 hour. phenol and 20 parts of the adduct of

After cooling, the low-viscosity 4 mol of ethylene oxide obtained is added to nonylphenol in 500 parts

Solution of possible minor impurities - water dissolved. To this are added 20 parts of glacial acetic acid and

filtered off. The solution obtained in this way is also 8 parts of alginate thickening, which is

Stable at low temperatures and can be removed without slipping. Then with water on total

precipitation of dye made up to 1000 parts with any amount of water. With the resulting fleet

be diluted. if you impregnate woolen tops on a foulard,

For dyeing 100 parts of nylon 6 flake, which is then steamed at 100 ° C for 30 minutes.

1200 parts of water of 50 to 6O ⁰ C in a pack After rinsing and drying, a

apparatus is first given 1 part of 60 reddish yellow color dissolved in water with excellent fastness

Sulfuric acid half ester triethanolamine salt of a unity.

Addition product of 80 mol of ethylene oxide with "· ·,

1 mole of oleyl alcohol and 1 part of the addition ^P

products of 7 moles of ethylene oxide to 1 mole of isooctyl- 62.4 parts of the monoazo diazotized

phenol and leaves the liquor for about 10 minutes 65 l-amino-2-oxy-5-nitrobenzene and acetoacetic anilide

circulate. Subsequently, 11 parts of the dye are used in a mixture of 100 parts of dipropylene

substance solution to bring the liquor entered in the course of 30 micro-glycol and 100 parts of N-methylpyrrolidone,

utes to boil and stains IV ₂ hours at this Then 25 parts of cobalt (II) chloride are added,

7 8

heated to 8O ⁰ C and then added with 27 parts. .

50 ° / ₀ sodium hydroxide solution. After stirring for 1 hour at B e ι s ρ ι e 1 7

90 ⁰ C is from a slight precipitate 71.4 parts of the azo dyes from the diazo and

sucked off. A coupling component of Example 6 and 32 parts are obtained even at a lower temperature

Temperature-resistant sodium dichromate that can be diluted with water as required is mixed at HO ⁰ C

thin liquid solution. from 110 parts of glycerol and 110 parts of butyrolactone

6 parts of the solution thus obtained are added in one and 2 hours at this temperature

Reel skid mixed with 100 parts of polyamide charmeuseware. After the separation of any previous

in 3000 parts of water at 50 ⁰ C and 1 part of the existing impurities obtained by filtration

The triethanolamine salt of the terminally sulfated anion is a stable, water-miscible solution,

storage product of 80 moles of ethylene oxide in oleyl- 2 parts thereof are in a reel vat to 100 parts

alcohol. The dye liquor is brought out in 30 minutes from len woolen fabric and a homogeneous mixture

for boiling and coloring for 1 hour at boiling temperature. 4000 parts of water at 50 ^° C., 1 part of the sodium salt of

After rinsing and drying, a red sulfuric acid half-ester of an addition product is obtained

pungent yellow coloring of excellent levelness 15 of 80 moles of ethylene oxide on 1 mole of stearyl alcohol and

and authenticity. 1 part glacial acetic acid. The dye liquor is inside

". -I ^ brought and ³⁰ minutes to boiling temperature

Leave ΰ e 1 s ρ 1 el 5 _l hour at this temperature.

65 parts of the monoazo dye from l-amino-2-oxy- After rinsing and drying, a

4-nitrobenzene and l-phenyl-3-methylpyrazolon-5 and 20 blue-violet-dyed wool fabric with excellent

32 parts of sodium bichromate be at 100 ⁰ C in a light, rubbing and wet fastness.

A mixture of 60 parts of propylene glycol, 60 parts is obtained in an analogous manner using 2 parts

Dimethylformamide and 60 parts of ethylene carbonate from l-Amino ^ -methoxy ^ -sulfamido-S-methyl-

entered and ^{stirred at 100 0} C for 1 hour. Of benzene and l-phenyl-3-methylpyrazolone with sodium

a possibly existing small residue 05 bichromate prepared 1: 2 chromium complex solution

is filtered off. A thin liquid solution is obtained, a red, very real wool dye,

which even when cooling to-2O ⁰ C runny and. .

remains without precipitation and can be mixed with water as desired. Example 8

can be diluted. 83.2 parts of the monoazo from diazotized!

45 parts of this solution are added to an aqueous 30 l-amino-2-oxy-5-sulfonamidobenzene and 1-carbo-

Solution of 25 parts of the trisodium salt of methoxyamino-7-oxynaphthalene and 32 parts of sodium

Dodecylbenzene sulfonic acid, 15 parts of the annealing are from bichromate at 100 ⁰ C in a mixture

products of 2 moles of propylene oxide and 5 moles of ethylene - 80 parts of diethylene glycol mono-n-butyl ether, 80 parts

oxide of Tsononanol and 15 parts of p-chlorophenylene dimethylformamide and 60 parts of ethylene glycol

added glycol ether in 800 parts of water. Then entered 35 monoacetate and then 1 hour

Finally, 5 parts of glacial acetic acid are added and the mixture is filled with stirring at 115.degree. You get a thin,

Water to 1000 parts. With the stable, cold-resistant solution thus obtained.

Padding liquor is impregnated with needle felt made of polyamide- From 30 parts of this solution, 10 parts of the tri-

6 fibers needled onto a jute fabric. ethanolamine salt of decylbenzenesulfonic acid, 8 parts

Subsequently, one steams for 4.5 minutes at 100 ⁰ C 40 len of the adduct of 2 mol of propylene oxide

Saturated steam temperature on a sieve drum steamer and 5 moles of ethylene oxide in isodecanol, 7 parts

and, after washing and drying, a p-Chlorphenylmonoglykoläther and 30 parts of 60 ° / ₀ sodium

deep red colored material which, after solidifying acetic acid, is used to prepare a printing paste with which

loaded with plastic dispersions based on acrylic acid wool sliver on a Vigoureux printing machine

derivates a needle felt floor covering with excellent 45 prints. Then the dye is through

Neter light, rub and wet fastness results. lstündiges steaming at 100 ⁰ C fixed in a saturated steam atmosphere. After rinsing, drying and

Example 6 Stretching gives a bluish gray, uniform one Coloring of excellent washing, wet

71.4 parts of the monoazo from diazotized 50 and rub fastnesses.
l-amino-2-methoxy-5-sulfamidobenzene and / J-naph-. .
thol are in a mixture of 100 parts of triethylene Example 9
glycol mono-n-butyl ether and 100 parts of methyl 37.3 parts of the monoazo dyes registered from diazotized formamide and then with 30 parts of a 1-amino-2-oxy-5-eulfonamidobenzene and 1-phenyl analogue of Example 2, aqueous cobalt-55 prepared 3-methylpyrazolon-5, 33.9 parts of the Monoazofarbhydroxydpaete crosslinked. The Miechung is then l-amino-2-oxy-5-nitrobenzene stirred etoffs of diazotized 2 hours at 90 to 100 ⁰ C. After freshly filtering and l-phenyl-3-methylpyrazolone-5 and 60 parts, a cold-stable, water-precipitated chromium (Iir) hydrate paste is obtained which can be diluted with any solution. content of 13% Cr ₂ O ₃ are mixed at 95 ° C

100 parts of wool tops are at 5O ⁰ C in a 60, 100 parts of dipropylene glycol, 10 parts of mono-bath of 2200 parts of water, the ethanolamine in Example 1 and carried 100 parts of dimethylformamide were called auxiliaries and 3 parts of the dye and then for 1 hour at 120 stirred ° C, in a solvent and optionally Kammzugfärbeapparat this gives a stable dye solution which is heated in 30 minutes at 100 ⁰ C with water bath. can be smelled in any proportion.
The dyeing is carried out for 1 hour at this temperature and 65 3 parts thereof are obtained, together with 20 parts of the, after rinsing and drying, a bluish-tinted red sodium salt of the end sulfated addition-dyed woolen tops with excellent friction, products of 2 moles of ethylene oxide in nonylphenol wash and lightfastness. and 20 parts of the adduct of 4 Mo ^

Claims (1)

9 10 Ethylene oxide on nonylphenol in 500 parts of water. A level, bluish-tinted red coloration is obtained with dissolved. 20 parts of glacial acetic acid and 8 parts of excellent fastness properties are added.
Alginate thickening slurried with ethanol. . .
would. Example U is then added to a total of 1000 parts with water
filled up. Impregnated with the resulting liquor 5 To 500 parts of water are added 30 parts of the Triman on a wool padding, which is then steamed at 100 ° C. for 30 minutes at the ethanolamine salt of p-decylbenzenesulfonic acid. After 20 parts of the adduct of initially 2 moles of rinsing and drying, a reddish-tinged orange propylene oxide is obtained, then 5 moles of ethylene oxide on 1 mole of dyeing with excellent fastness properties. Iso-nonanol, 20 parts of p-chlorophenyl monoglycol ether,. ίο 5 parts of glacial acetic acid and 5 parts of oxethylated carob example lü kernel flour ether, slurried with 10 parts of ethanol 61.6 parts of the monoazo dye was made from diazotized. Then add 1 part of the dye l-Amino-2-oxy-4-nitrobenzene and 2-aminonaphthalene solution from Example 1, 8 parts of the dye solution and 30 parts of cobalt hydroxide paste, analogous to Example 3 and 1 part of the dye solution from Example 5 game 2 made from 26 parts of cobalt (I I) chloride 15 added and made up to 1000 parts with water. With was, are impregnated in a mixture of 95 parts of this liquor on a padder Dimethylformamide, 95 parts of diethylene glycol mono- a carpet made of textured continuous polyamide fibers, methyl ether and 12 parts of diethanolamine, whose base fabric consists of jute fibers. The Stirred for 1 hour at HO ⁰ C and then filtered. Textiles are heated for 5 minutes at a saturated steam temperature With 2 parts of this solution are steamed analogously to the 20 door from 100 to 101 ° C, rinsed and dried. Procedure given in Example 2 100 parts of woolen flakes A brown coloration of excellent quality is obtained colored with the addition of a part of glacial acetic acid. The resul- equality and authenticity,
animal blue-gray color has excellent light- and wet fastness properties. Claim: ο · ■ 1 11 ² 5 Use of highly concentrated, stable, Example 11 _{miscible with} water in any ratio, In a winch is added to 100 parts of knitted fabric sulfonsäuregruppenfreie 1: 2 Metallkomplexfarbaus textured polyamide-6,6-continuous fiber and 3000 TEI materials in oxygen-containing, with water in any len water of 5O ⁰ C, 3 parts of sulfated oleic acid ratio miscible solvents containing butanolamide and 1 part of the adduct 30 stock solutions, which are immediately replaced by metallivon 9 parts of ethylene oxide on stearylamine and lets the corresponding metal-free dyes circulate the dye liquor for 10 minutes. Subsequently obtained in the solvents mentioned, 3 parts of those described in Example 5 are added to prepare dyebaths or printing dye solution, the liquor brings paste in 30 minutes for dyeing textile material from stickzum boiling and dyes for 1 hour at this temperature . 35 fabric-containing fibers.