DE1170898B - Process for dyeing and printing cellulose textile materials - Google Patents

Description

FEDERAL REPUBLIC OF GERMANY

GERMAN

PATENT OFFICE

EDITORIAL

Boarding school Class: D 06 ρ

German class: 8 m -1/04

Number: 1170 898

File number: F 23474IV c / 8 m

Filing date: July 15, 1957

Opening day: May 27, 1964

It has been found that fibers, fabrics, films and the like made from negative or regenerated cellulose dyeings or prints with excellent wet fastness are obtained if such dyes are applied to the material to be dyed applies which one or more with polybasic inorganic acids or their organic Derivatives have esterified sulfonic acid hydroxyalkylamide groups in which the oxygen atom the esterified hydroxyalkyl group and the nitrogen atom of the amide group through a chain separated by 2 or 3 carbon atoms, except those by the patent process 1 066 987 dyes used and the dyes produced by the process of patent 1 091 259, applies to the material to be colored, the material treated in this way, preferably in alkaline Medium subjected to the action of elevated temperature and then in neutral or alkaline aftertreated aqueous liquor.

The compounds on which the dyes to be used according to the invention are based can have a wide variety of constitutions. You can, for example, the group of azo dyes, belong to the anthraquinone dyes or the azaporphin dyes. It shouldn't be here, however are dyes, which in German Patent 1,066,987 for dyeing and printing of Cellulose is recommended and its production is described in German Patent 1,091,259.

The not yet esterified dyes contain one or more times in the molecule sulfonic acid-ß-hydroxyäthylamid- or sulfonic acid-γ-hydroxypropylamide groups, which can still be substituted by alkyl radicals in the carbon chain. The dyes can incidentally usual substituents, advantageously also solubilizing groups, such as Sulfonic acid and / or carboxylic acid groups. Connections that do not have any or have very little affinity for the materials to be colored; the use of such dyes enables complete detachment of the dye molecules that are not firmly bound to the fiber final aftertreatment in neutral or alkaline aqueous liquor.

The dyes to be used can be prepared, for example, by combining sulfonic acid hydroxyoxyalkylamides of dye precursors - when using azo dyes, diazo or azo components - to form the corresponding dyes, or by preparing sulfochlorides of dyes, reacting them with alkanolamides and so on obtained color process for dyeing and printing
Cellulosic textile materials

Applicant:

Paint factories Bayer Aktiengesellschaft,

Leverkusen

Named as inventor:

Dr. Karl-Gustav Kleb, Leverkusen

sulfonic acid hydroxyalkylamides with di- or polybasic inorganic acids or their organic derivatives converted into the corresponding esters in a known manner. The esters of the with Dyes substituted with sulfonic acid hydroxyalkylamide groups can also be obtained by combining precursors, which already contain sulfonic acid hydroxyalkylamide groups esterified with the acids mentioned, or by reacting the dye sulfochlorides with esters of aminoalkanols.

The dyes containing ester groups are neutral or alkaline in the form of the alkali metal salts Solution isolated. They are in substance or in solution at room temperature in neutral or alkaline Medium resistant.

They are preferably used from an aqueous solution that is mixed with alkaline substances, preferably alkali metal hydroxide or alkali metal carbonate, or converting into alkaline substances Compounds such as alkali bicarbonate can be added. Other auxiliary products can be added to the solution are added, but should not react in an undesirable manner with the dyes. Such additives are, for example, surface-active substances, such as alkyl sulfates, or the migration of the dye preventive substances or auxiliary dye products, such as urea, or indifferent thickeners, such as Oil-water emulsions.

The solutions or pastes thus prepared are applied to the material to be dyed, for example by padding in the padding or by printing, and then heated to a higher temperature for some time, preferably 60 to 150 ⁰ C. This process can be carried out in the hot flue, in the steamer, on heated rollers or by placing in heated, concentrated salt baths, either individually or in any order one after the other.

409 597/339

3 4

After the fixation has taken place, the material to be dyed becomes hot Example 1

rinsed and, if the intended use of the colored material requires, soaped at the boil, nickel phthalocyanine- (3) -tetrasulfochloride being removed with possibly insufficiently fixed residues of twice the molar amount of 2-aminoethanol to the dye. 5 corresponding amide reacted, the remaining sulfo-Man obtained excellent wet-fast dyeings, saponified chloride groups and the product obtained, although the preferred dyes to be used, esterified with sulfuric acid in a known manner. 5 g or their hydrolysis products, little or no of this dye, will have an affinity for the material to be dyed in 80 ml of water after addition. of 5 g of sodium hydroxide, 4 g of urea and 0.5 g. This solution of crude esterified Sulfonsäurealkanolamidgruppe is soaked in the diazo cotton fabric and contain 10 Mikomponente in the hot flue, the colored grooves to 120 ⁰ C can be heated. After subsequent materials by reductive cleavage of the azo bond boiling soap in a soda-alkaline bath during the applied dyes with sodium dithionite for 20 minutes, a very washfast greenish-blue color will be discolored. The material is then obtained in acidic dyeing with good lightfastness. Medium with nitrite solution and then in alkaline,

neutral or acidic range with the solution of Example 2

for the production of the original dye

Treated azo component used, so the reaction of nickel phthalocyanine

the dye or dyeing with the same fastness 20 (3) tetrasulfochloride with four times the molar amount of properties. This surprising result of the nickel phthalocyanine produced by 2-aminoethanol suggests that the dye molecule (3) -tetrasulfo-oxyethylamide is esterified with sulfuric acid by chemical bonding to the material to be colored. 4 g of this is color-bound. substance are dissolved in 100 ml of a solution that contains 3 g of sodium in French patent 976 047 is a 25 hydroxide, 5 g of urea and 0.5 g of Turkish red oil method for fixing certain organic substances. After adding 5 g of a tragacanth water-soluble compounds on textile materials solution containing 60 g of tragacanth in 1000 g of solution, described. In this process, come under the dye solution in the padding on cotton including organic dyes are used, popeline padded immediately and at least once ₂ NHROX 30 followed by heating the impregnated fabric, the grouping SO 10 minutes 120 ⁰ C. Then contain, where R is a chain of 4 or 5 atoms, is rinsed hot and soaped at the boil for 20 minutes, of which at least 3 carbon atoms are obtained good brightening, water-solubilizing groups, in particular medium and light fastness, a polybasic inorganic acid. 35

The compounds are based on Example 3 to be colored

Materials applied and then one

Heat treatment in the alkaline range under nickel phthalocyanine (3) tetrasulfonyl chloride is used in the

threw. Compared to the weakly alkaline medium with an excess of this method, The colorations provided have the colorations according to 40 d. H. with more than four times the molar amount present invention implemented improved intrinsic 2-aminoethylsulfuric acid half-ester. 4 g des up, especially improved wet fastness properties. colored object isolable by salting out with potassium chloride of the German patent specification 1,066,987 substance are analogous to the information in Example 5 is a process for dyeing and printing cellulose-dissolved, fixed on cotton fabric and post-treated, containing fiber materials, in which the materials 45 are used. The coloration obtained is similar to that of Example 1 dyes with such organic dyes, impregnated obtained dyeing, or printed, in addition to at least one and pre- B e i s d i e 1 4

preferably more than one acidic water-solubilizing agent

Group, among other things, at least one sulfur- that from the condensation product of 4-bromine-

acid ester substituents on a / 3-position carbon 50 l'-methylanthrapyridone with 4-aminotoluene atom of the aliphatic chain of an ermolekül in the dye treatment with excess chlorosulfonic acid Any sulfonic acid alkylamide residue present is converted into sulfochloride with 2-aminoethanol bundles contains; the materials treated in this way are reacted with sulfonic acid-ß-oxyethylamide, are then subjected to a heat treatment in the presence of esterification with sulfuric acid becomes a dye subject to inorganic acid-binding agents. 55 obtained, which is fixed on cellulose as follows The subject of German patent specification 1091259 can be: The dye is in aqueous solution, is a process for the production of phthalocyanine- 100 g urea, 5 g turkey red oil and per liter dyes, in which a copper phthalocyanine 20 g sodium hydroxide is added, on cotton polysulphonic acid chloride applied with / 3-oxethyl popeline, among other things. The prepared tissue will aminesulfuric acid half-ester, which is heated to 130 ° C for at least 10 minutes in the ethylene group 60, then can be substituted by lower alkyl groups, rinsed hot and soaped at the boil. You get one in such a way that the dye obtained is lightfast blue-tinged red coloration, which is very stable there is still at least one nucleus-bound sulfonic acid against repeated hot washes. group has; instead of with / J-Oxäthylaminschwefel-. .

Acid half esters can also be condensed with the 65 B e 1 s ρ 1 e 1 5

Free oxethylamine reacted and the resulting 20 g of the dye, which by condensation

Dye then with a sulfating agent of copper phthalocyanine (4) tetrasulfochloride with be treated. ß-Aminoethyl hydrogen sulfate (sulfuric acid half-ester

des / J-aminoethanol) in alkaline solution is, in 1000 ml of an aqueous solution containing 50 g of urea, 5 g of Turkish red oil, 40 ml of sodium hydroxide solution (38 ° Be) and 50 g of an alginate thickening 35: 1000, dissolved. With this solution will impregnated with bleached cotton nettle, the soaked fabric dried at 80 ° C and steamed Treated for 5 minutes at 105 ° C. After rinsing and boiling soaps, you get an excellent one lightfast greenish blue coloring with very good fastness to water, washing, soda boiling and solvents.

Instead of cotton nettle, other fabrics made of cotton, copper cellulose or -reyon, viscose rayon or -reyon or other cellulose fibers are dyed.

Example 6

Copper phthalocyanine tetrasulfochloride, which is obtained from copper phthalocyanine by heating with chlorosulfonic acid was prepared, is reacted in an aqueous alkaline solution with ß-aminoethyl hydrogen sulfate. 30 g of the isolated and dried dye are dissolved in 400 ml of an aqueous solution which 50 ml sodium hydroxide solution (38 ° Be), 100 g urea, contains 5 g Turkish red oil, dissolved, with 350 g of an alginate thickener, which contains 30 g of alkali alginate in 1000 g of thickening, stirred and the paste obtained adjusted to 1000 g with water. Cotton fabric printed with this paste is dried at 80 ° C and steamed in a steamer for 10 minutes at 105 ° C. After rinsing and soaking, a greenish blue color is obtained Print with very good wash, solvent and lightfastness.

Prints on other fabrics made from fibers made from native or regenerated cellulose produce similar, slightly different results depending on the type of fiber.

Example 7

The dyeings on fibers made from native fibers are very good for water, washing, soda cooking and solvents or regenerated cellulose, if the fibers are used as described in the previous examples Treated with dyes which are prepared by known processes by converting sulfonic acid groups into Colorants from the starting components listed in the table below are built up, all sulfonic acid groups in the corresponding sulfonic acid esterified with sulfuric acid - [/ S-oxyäthylamide] converts.

The conversion of the sulfonic acid groups in the dyes or dye precursors into sulfochloride groups is expediently carried out by the action of chlorosulfonic acid and thionyl chloride. From the In the reaction mixture, the sulfochlorides are isolated by adding ice and in aqueous solution pH 8 to 10 with, for example, / I-aminoethyl hydrogen sulfate implemented. The final dyes are usually isolated by salting out with potassium chloride. they are generally very easily soluble in water.

Starting azo dyes obtained by coupling

Diazo component Coupling component Coloring of the ent
speaking with
sulfuric acid
esterified suIf on
acid- [ß-oxyethyl-
amide] on cellulose 4-aminobenzene-1-sulfonic acid l- [phenyl-4'-sulfonic acid] -3-methyl-
pyrazolone- (5) yellow 4-amino-1-methylbenzene-2-sulfonic acid the same yellow 3-aminobenzene-1-sulfonic acid the same yellow 3-amino-6-chlorobenzene-1-sulfonic acid the same yellow 3-aminobenzene-1-sulfonic acid l- [2'-chlorophenyl-5'-sulfonic acid] -3-methyl-
pyrazolone- (5) yellow 4-aminobenzene-1-sulfonic acid the same yellow 4-amino-1-methylbenzene-2-sulfonic acid the same yellow the same l- [2 ', 5'-dichlorophenyl-4'-sulfonic acid] -
3-methyl-pyrazolone- (5) yellow 4-amino-1-methylbenzene-2-sulfonic acid l- [2'-methyl-6'-chloro-4'-sulfophenyl] -
3-methyl-pyrazolone- (5) yellow 3-amino-6-chlorobenzene-1-sulfonic acid the same yellow 3-aminobenzene-1-sulfonic acid l- [4 ', 8'-disulfonaphthyl- (2')] -3-methyl-
pyrazolone- (5) yellow 2-amino-1-oxybenzene-4-sulfonic acid the same yellow 4-Amino-1-methylbenzene-2-sulfonic acid the same yellow 2-aminobenzene-1-sulfonic acid the same yellow 4-aminobenzene-1-sulfonic acid the same yellow 2-Amino-1-oxybenzene-4-sulfonic acid l- [2'-chloro-5'-sulfophenyl] -3-methyl-
pyrazolone- (5) yellow

(Continuation)

Diazo component Coupling component Coloring of the ent
speaking with
sulfuric acid
esterified sulfone
acid- [ß -oxyethyl-
amide] on cellulose 2-Amino-1-oxybenzene-4-sulfonic acid l- [2 ', 5'-dichlorophenyl] -3-methyl-
pyrazolone- (5) yellow 2-amino-4-chloro-1 -oxybenzene-6-sulfon-
acid l-phenyl-3-methyl-pyrazolone- (5) yellow 4-Amino-1-methylbenzene-2-sulfonic acid 1-oxynaphthalene-4-sulfonic acid Red orange the same l-oxynaphthalene-5-sulfonic acid Red the same l-oxynaphthalene-6-sulfonic acid Red orange the same 1-oxynaphthalene-7-sulfonic acid Red orange the same 1-oxynaphthalene-4,8-disulfonic acid Red the same 2-oxynaphthalene-3,6-disulfonic acid Red the same 2-oxynaphthalene-6-sulfonic acid Red orange 4,4'-diaminodiphenyl-2,2'-disulfonic acid the same Red orange the same 1-oxynaphthalene-4-sulfonic acid Red orange the same 1-oxynaphthalene-5-sulfonic acid Red 4,4'-diamino-3,3'-dichloro-diphenyl 2-oxynaphthalene-3,6-disulfonic acid Red the same 1-oxynaphthalene-4,8-disulfonic acid Red the same l-oxynaphthalene-3,6-disulfonic acid Red 2-aminobenzene-1-sulfonic acid 2-oxynaphthalene-6-sulfonic acid Red orange 3-Amino-4-methoxybenzene-1-sulfonic acid the same Scarlet fever 2-Amino-1-oxybenzene-4-sulfonic acid the same violet 3-Amino-4-methoxybenzene-1-sulfonic acid l- (2'-Cxy-3'-naphthoylamino) -2-methyl-
benzene sulfonic acid Red the same l- (2'-Oxy-3'-naphthoylaminoV2-methyl-
4-methoxybenzenesulfonic acid Red 2,5-dichloro-4-aminobenzene-1-sulfonic acid l- (2'-oxy-3'-naphthoylamino) -2-methoxy-
benzene sulfonic acid orange 3-chloro-4-aminobenzene-1-sulfonic acid the same orange 2-aminonaphthalene-4,8-disulfonic acid 3-amino-l-methylbenzene, dye in the
Urea transferred orange l-amino-S-oxynaphthalene ^ o-disulfone-
acid S-amino ^ -methoxy-l-methylbenzene,
Dye converted into urea Red 2-amino-1 -oxy-4-chloronaphthalene-
6-sulfonic acid 1- (3'-sulfophenyl) -3-methyl-pyrazolone- (5),
Chromium complex of the dye Red l-amino-2-oxynaphthalene-4-sulfonic acid 1- (3'-sulfophenyl) -3-methyl-pyrazolone- (5),
Chromium complex of the dye Bordo

Diazo component Further diazotized
Middle component End coupling component Coloring of the
Final dye
made of cellulose 1 -aminonaphthalene-
5-sulfonic acid 1-aminonaphthalene 1 -phenylaminonaphthalene-
8-sulfonic acid Brown

(Continuation)

10

Diazo component Further diazotized
Middle component Decoupling component 4,4'-di- [6-methyl-benzothiazolyl- (2 ")] -azobenzene-disulfonic acid Γ N i Cl \
j \\ (SO ₃ H) ₂ -SO ₃ H Coloring of the
Final dye
on cellulose C ₂ H HO ₃ SV ' \ ^Ν νΛ ° \ “O ₃ H / yellow ' ! O ^ NV CH ₂ ^ egg violet Cl ^C 2 ^H 5 (SO ₃ H) ₁ \ N / \ O ^ \ / N .. \ i Il I ^! -
ti -.- O, ^{y /%} N ^ ^ \ H ₂ - "^; ^ blue Cl
I. \ / C ₂ H ₅ C ₂ H ₅ : -. CH ₂ : h ₂ -ν- _/: \ _N-c ; , _ffi j_ (
/ ' c ^ blue i
[
ς

Example 8

Very washfast dyeings are also obtained on cellulose if the dyeing material is used according to the Information in the preceding examples treated with dyes obtained from the following starting compounds are available:

Azo dyes obtained by coupling

Diazo component Coupling component coloring
on cellulose 3-aminobenzene-1-sulfonyl-aminoethyl-
hydrogen sulfate 1-phenyl-3-methyl-pyrazolone- (5) yellow 5-aminobenzene-1,5-disulfonylaminoethyl
hydrogen sulfate the same yellow the same 2-oxynaphthalene orange 409 597/339

(Continuation)

Diazo component Coupling component coloring
on cellulose 2 mol ^ amino-l-methylbenzene-l-sulfonyl-
aminoethyl hydrogen sulfate 1 mole of urea
l- (3'-aminophenyl) -3-methyl-pyrazolone- (5) yellow 2 moles of 3-aminobenzene-l-sulfonylaminoethyl
hydrogen sulfate the same yellow 2 moles of 2-amino-3-chloro-l-methylbenzene
5-sulfonylaminoethyl hydrogen sulfate the same yellow 2 mol + ■ amino-l-methylbenzoM-sulfonyl-
aminoethyl hydrogen sulfate 1 mole of urea from l- (3'-aminophenyl) -
pyrazolone- (5) -3-carboxylic acid yellow
orange the same 1 mole of urea
1- (4'-aminophenyl) -3-methyl-pyrazolone- (5) yellow 2 MoI 3-Ammo-4-methoxybenzene-1-sulfonyI-
aminoethyl hydrogen sulfate the same yellow S-Amino- ^ methoxybenzene-1-sulfonylamino-
ethyl hydrogen sulfate 1- (2,3'-Oxynaphthoylamino) -2-methylbenzene Red the same l- (2 ', 3'-oxynaphthoylamino) -2-methoxy-
benzene Red the same 1 - (2 ', 3' -oxynaphthoylamino) benzene Red the same 1- (2 ', 3'-oxynaphthoylamino) -4-chlorobenzene Red the same l- (2 ', 3'-oxynaphthoylamino) -2,4-dimethoxy-
benzene Red the same l- (2 ', 3'-oxynaphthoylamino) -2-methyl-
4-methoxybenzene Red 2 moles of S-amino- ^ methoxybenzene-l-sulfonyl-
aminoethyl hydrogen sulfate 1 mole of 1,4-terephthaloyl-bis-acetyl-
(2-methoxy-5-methyl-4-chloroaniline) yellow the same 1 mole of 1,4-terephthaloyl-bis-acetyl-
(2,4-dimethoxy-5-chloroaniline) yellow 4-amino-2,5-dichlorobenzene-l-sulfonylamino-
ethyl hydrogen sulfate 1- (2 ', 3'-oxycarbazoylamino) -4-chlorobenzene Brown the same l- (2 ', 3'-oxynaphthoylamino) -2,5-dimethoxy-
benzene Red 1,3-Dimethyl-4-aminobenzene-5-sulfonylamino-
ethyl hydrogen sulfate l- (2 ', 3'-oxynaphthoylamino) -4-methoxy-
benzene Scarlet fever the same 1- (2 ', 3'-oxycarbazoylamino) -4-chlorobenzene Brown 2-aminobenzene-1-sulfonylaminoethyl-
hydrogen sulfate l- (2 ', 3'-oxynaphthoylamino) -4-methoxy-
benzene Scarlet fever 3-aminobenzene-l-sulfonylaminoethyl
hydrogen sulfate the same Scarlet fever 2,5-dichloro-4-aminobenzene-l-sulfonylamino-
ethyl hydrogen sulfate the same Red S-amino ^ -methoxybenzene-l-sulfonylamino-
ethyl hydrogen sulfate the same Red 2-ChloΓ-4-aminobenzene-1-sulfonylaminoethyl-
hydrogen sulfate the same Red 4,4'-bis [3'-aminobenzene-1 '-sulfonamido] -
diphenyl-2,2'-disulfonylaminoethyl
hydrogen sulfate the same Scarlet fever 3-amino-4-methoxybenzene-1-sulfonylamino-
ethyl hydrogen sulfate l- (2 ', 3'-oxynaphthoylamino) -2-methoxy-
benzene Red 2-amino-2-methylbenzene-3,5-di- (sulfonyl-
aminoethyl hydrogen sulfate) the same Scarlet fever 3-amino-4-methylbenzoyl- [l'-amino-
naphthalene-3 ', 7'-di- (sulfonylaminoethyl-
hydrogen sulfate)] the same Red

(Continuation)

14th

Diazo component coupling component

Coloring on cellulose

2-amino-diphenyl ether-4,4'-di- [sulfonylaminoethyl hydrogen sulfate] 1- (2 ', 3'-oxynaphthoylamino) -2-methoxybenzene

At ph = 5 coppered product comes out

2-Amino-6-chloro-1-oxybenzene-4-sulfonylaminoethyl hydrogen sulfate

-Phenyl-3-methyl-pyrazolone- (5)

Coupling products converted into urea

2-Amino-1-methylbenzene-4-sulfonylaminoethyl hydrogen sulfate

the same

2-aminonaphthalene-4,8-dis [sulfonylaminoethyl hydrogen sulfate]

the same
the same

3-amino-1-methylbenzene

3-amino-4-methoxy-1-methylbenzene
3-amino-1-methylbenzene

3-amino-4-methoxy-1-methylbenzene
3-acetamino-1-aminobenzene

Red

orange

yellow

yellow
yellow

Orange brick red

Example 9

Dyes which can be used for the process according to the invention are also obtained if the im the following listed dyes using chlorosulfonic acid and thionyl chloride converted into the sulf ochloride and this in the aqueous-alkaline range with 2-aminoethyl hydrogen sulfide at implements.

You get very good water-, wash- and boil-fast dyeings and prints if you use materials Cellulose fibers treated with these dyes as described in the previous examples.

Azo dyes obtained by coupling

Diazo component Coupling component Coloring of the
Final dye
on cellulose
hold
materials 4-amino-1-methylbenzene 1-phenyl-3-methyl-pyrazolone- (5) yellow 2-methoxy-1-aminobenzene l- (2 ', 3'-oxynaphthoylamino) -4-methoxy-
benzene Red 1-methoxy-2-aminobenzene-4-benzylsulfone l- (2 ', 3'-oxynaphthoylamino) -2-methoxy-
benzene Red 2-methoxy-1-aminobenzene the same Red the same l- (2 ', 3'-oxynaphthoylamino) -2-methyl-
4-methoxybenzene Red 1-methoxy-2-aminobenzene-4-benzylsulfone the same Red 2,5-dichloro-1-aminobenzene 1- (2 ', 3'-oxynaphthoylamino) benzene Brownish red 3-aminobenzene-1-sulfonic acid l- (2 ', 3'-oxynaphthoylamino) -4-methoxy-
benzene Red 2-chloro-5-aminobenzene-1-sulfonic acid l- (2 ', 3'-oxynaphthoylamino) -2-methoxy-
benzene Red 3-Amino-4-methoxybenzene-1-sulfonic acid l- (2 ', 3'-oxynaphthoylamino) -2,4-dimethoxy-
5-chlorobenzene Red

Coloring coloring of the final product

on cellulosic

materials

4-phenylamino-1'-methyl-anthrapyridone

4- (4'-methylphenylamino) -l-methyl-anthrapyridone 4- (3'-chlorophenylamino) -l-methyl-anthrapyridone. 4- (4'-Benzylphenylammo) -l-ethyl-anthrapyridone .. Yellow tinge red
Bluish red
Yellowish red
Bluish red

(Continuation)

16

Dyes

Coloring of the final product

on cellulosic

materials

6- (4'-Methylphenylamino) -2-diphenyl- (4) -anthrapyrimidine 6- (4'-Benzylphenylamino) -2-diphenyl- (4) -anthrapyrimidine.

1,4-di (4'-methylphenylamino) anthraquinone

1,4-di (2 ', 6'-dimethylphenylamino) anthraquinone

1,4-Di- (2'-methyl-6'-ethylphenylamino) anthraquinone

1,4-di (2 ' ₅ 6'-diethylpheny] amino) anthraquinone

1,4-di- (2 ', 6'-diethyl-4'-methylphenylamino) anthraquinone. 1,4-di- (2 ', 4'-dimethyl-6'-ethylphenylamino) anthraquinone.

1,4-di (2 ', 4', 6'-trimethylphenylamino) anthraquinone

1,4-di- (4'-methylphenylamino) -5-oxy-anthraquinone

1,4-Di- (4'-methylphenylamino) -5,8-dioxy-anthraquinone ...

1,4-Di- (4'-methylphenylamino) -6-chloro-anthraquinone

1,4-di (4 ', 6'-dimethylphenylamino) anthraquinone

1,4-di- (4'-methylphenylamino) -7,8-dioxy-anthraquinone ... 2,7-bis-diphenyl- (4) - [l ': 9'-4 ": 10"] - anthradipyrimidine

Scarlet fever

Red

Blue green

blue

blue

blue

blue

blue

blue

green

green

green

green

green

Yellow-brown

Example 10

30 Cellulosef asern treated with Azofarbstoifen according to the previous examples Produce dyeings with good water, washing and solution coupling of the following components medium fastness is obtained by leaving out materials:

Coupling component coloring Diazo component on cellulose
hold l- (2 ', 3'-oxynaphthoylamino) -2-methoxy-
benzene-5-sulfonylaminoethyl hydrogen
sulfate materials 2-aminobenzene-1-sulfonylaminoethyl-
hydrogen sulfate the same Red 4-amino-1-methylbenzene-2-sulfonylamino-
ethyl hydrogen sulfate the same Red 3-aminobenzene-1-sulfonylaminoethyl-
hydrogen sulfate the same Scarlet fever 3-amino-4-methoxybenzene-l-suh ° onylamino-
ethyl hydrogen sulfate the same Red 1,3-Dimethyl-4-aminobenzene-5-sulfonylamino-
ethyl hydrogen sulfate the same Scarlet fever 4-amino-1-methylbenzene-3,5-di- [sulfonyl-
aminoethyl hydrogen sulfate] l- (2 ', 3'-oxynaphthoylamino) -4-methylbenzene-
5-sulfonylaminoethyl hydrogen sulfate Scarlet fever 2-aminobenzene-1-sulfonylaminoethyl-
hydrogen sulfate the same Red
orange 3-aminobenzene-l-sulfonylaminoethyl
hydrogen sulfate the same Red
orange 4-Amino-1-methylbenzoI-2-sulfonylamino-
ethyl hydrogen sulfate the same Scarlet fever 2-chloro-5-aminobenzene-l-sulfonylaminoethyl
hydrogen sulfate the same Scarlet fever !, S-dimethyl ^ -aminobenzene-S-sulfonylamino-
ethyl hydrogen sulfate the same Scarlet fever 3-amino-4-methoxybenzene-1-sulfonylamino-
ethyl hydrogen sulfate Red

(Continuation)

Coupling component coloring Diazo component on cellulose
hold l- (2 ', 3'-oxynaphthoylamino) -4-methylbenzene- materials 4-amino-1-methylbenzene-3,5-di- [sulfonyl- 5-sulfonylamino-ethyl-hydrogen sulfate Scarlet fever aminoethyl hydrogen sulfate] the same 2,3-dichloro-5-aminobenzene-l-sulfonylamino- Scarlet fever ethyl hydrogen sulfate the same 2-chloro-4-amino-1-methylbenzene-5-sulfonyl- Scarlet fever aminoethyl hydrogen sulfate the same 4,4'-bis [3'-aminobenzene-1 "-sulfonamido] - Red diphenyl-2,2'-di- [sulfonylaminoethyl- orange hydrogen sulfate 2-oxynaphthalm-6-sulfonylaminoethyl Copper complex bond of 2-amino-6-chloro hydrogen sulfate Bordo l-oxybenzene-4-sulfonylaminoethyl hydrogen sulfate

Example 11

According to the process described in Example 7, the coupling product of diazotized 3-aminobenzene-1-sulfonic acid with 1- [2'-chloro-5'-sulfophenyl] -3-methyl-pyrazolone- (5) is esterified with sulfuric acid Sulfonic acid-fß-oxy-ethylamide] and isolated as the potassium salt. 20 g of this dye are dissolved in 1000 ml of a solution containing 100 g of urea and 2 g of sodium dodecylbenzene sulfonate. With this solution, cotton fabric is impregnated in the foulard and dried at 6O ⁰ C. Then allowed to the tissue - in foulard turn - by running a solution s, the 15% potassium chloride and 4 ° / ₀ of sodium carbonate, and then heated by a 130 ⁰ C, molten alloy of 25 parts of lead, 12.5 parts of cadmium , 12.5 parts tin and 50 parts bismuth (Woods alloy) so that the residence time is 6 minutes. After rinsing and boiling soaps, the result is an extremely washable yellow color.

Claims (1)

Claim: Process for dyeing or printing cellulose textile materials, characterized in that that one dyes that one or more with polybasic inorganic acids or their organic derivatives esterified sulfonic acid hydroxyalkylamide groups in which the oxygen atom of the esterified hydroxyalkyl group and the nitrogen atom of the amide group separated by a chain of 2 or 3 carbon atoms, excluding those after the process of the patent 1,066,987 and the dyes used by the method of the patent 1 091259 produced dyes, applied to the material to be colored, the treated in this way Material, preferably in an alkaline medium, subjected to the action of elevated temperature and then aftertreated in neutral or alkaline aqueous liquor. Legacy Patents Considered:
German patents No. 1,066,987, 1,091,259. 409 597/339 5.64 © Bundesdruckerei Berlin