CA1067896A

CA1067896A - Water-soluble disazo dyestuffs

Info

Publication number: CA1067896A
Application number: CA249,442A
Authority: CA
Inventors: Fritz Meininger; Hermann Filzinger Klaus Fuchs
Original assignee: Hoechst AG
Current assignee: Hoechst AG
Priority date: 1975-04-04
Filing date: 1976-04-02
Publication date: 1979-12-11
Also published as: CH606308A5; FR2306241B1; DE2514856B2; DE2514856C3; FR2306241A1; GB1543173A; DE2514856A1; JPS51122128A; BE840388A

Abstract

Abstract of the Disclosure:

Novel valuable diazo dyestuffs of the formula

Description

~IL06~7~3~6 .

The present invention relates ~o novel water-soluble disazo dyestuffs, to a prooess for preparing them, and to their use.
~ he present invention provides novel water-soluble disazo dyestuffs which - in the form of the free acids - have the general ~ormula ~1) : ~ N--N-A-N -N-B-O-R ~1), . ` :

: in which A represents a benzene or naphthalene radical which is fTee from sul-~onic acid groups and which may optionally be substituted, for ex~mple, by al-ko y OT alkyl groups each having from 1 to 4 carbon atoms, by chlorine atoms, or by acetylamino, benzoylamino or trifluoromethyl g~oups, and B stands for the r~dical of a coupling component of the phenol series, the radical being free from sulfonic acid groups, and R is a hydTogen atom, the methyl, ethyl or ~-hydroxyethyl group or the benzene~, p-toluene- or p-chlorobenzene-sulfonyl radical, as well as a process for their preparation, which comprises diazotizing a diazo component of the general formula (2) ~ NH2 . (2 thereafter coupling the diazonium compound with a primary aromatic amine or with the corresponding sulfamic acid derivative thereof or the corresponding arylamino-methane-sulfonic acid derivative, all of which couple in the ~. ~
~ -2- ~ ~

iL0678~6 para-position to the amino group a~d have the ge~eral ~ormula : (3) H ~ A - ~H - Z (3) ~
wherein A is defined as above, and Z s~ands for a hydrogen atom, for a ma'l~ly sul~nic a~id .ad!~al ol tha fo mula -CH2~S03H or for a sulfonic acid group, d~azotizing the amino-azo dye~tuf~ thus obtained o~ the general ~ormula ~4~
. , .
~ N _ N-A-N~-Z
- ~ , , }~03S-C~-cH2-o2s , (~ ~
wherein A and Z are defined as abo~e, according to a known method,following a previous alkaline or acid hydrolytic sepa-ration o~ the methylene-sulfonic acid radical, if Z stands for-CH2-S03H, coupling sai~ aminoazo dyestuf~ with a coup-ling compone~t of the formula H-B-OX~ wherein B is defined as above) and reacting it optio:nally thereafter, in the pre-sence of acid-binding agents at a temperature o~ from 15 to 80Cs with dimethyl or diethyl sulfate under normal pressure~, or wlth methyl or ethyl-halides, for example methyl or e~hyl bromide, under pressure, with ethylene oxide or ethylene chlorohydrin under normal pressure or under pressure, or with benzene~, p-toluene- or p-chlorobenzene-sulfochloride under normal pressure at a pH value of from 8 to 12 and at a tem-perature in the range o~ from 15 to 80C, preferably 15 to The present inventio~ pro~ides in particular those dye-stu~fs of the above~mentioned form~lla (1), in which A stands ~or phenylene or naphthylene radicals, which may be substi-31 i~6~896 ~

tuted by alkoxy groups having from 1 to 4 ca~bon atoms, by alkyl groups havi~g ~rom 1 to ~ carbon atoms, by chlori~e atoms, acetylamino, benzoylamino and/or trifluoromethyl group~;
B stands for phenylene optionally substituted by alkyl groups having from 1 to 4 carbon atoms, alkoxy group~ having from 1 to 4 ~arbon atoms 9 by chlorine atoms, or by phenyl, hydroxy, nitr~ and/or bromi~e, and R is defined as above.
The diazo component of the formula ~2) is obtained by the reactio~ of nitro- or aminobenzene-B-chloroethylsulfones in an aqueous suspension or an aqueous alcoholic solution wlth sodium sulfite and substances ha~ing an alkaline effect, such as sodium or potassium hydroxide, sodium carbonate or ~odium hydrogenocarbonate; in the case of the nitrobenzene-B sulfoethylsulfone compounds, there is a catalytic reduction in an aqueous so~ution with hydrogen in the presence of common nickel cataly~ts. ~Iowever, the aminob~nzene--B-sulfatoethyl sulfone compounds are reacted preferably in an aqueous solu-tion with sodium sul~ite and alkali, to give the diazo com-pounds of the formula (2). The coupling of the diazonium salts prepared according to common methods from the amines of the formula (2) to yield the aminoazo dyestuffs of the general ~ormula (4) is effected in a strongly acid to sligh-t-ly acid pH range at a temperature of ~rom 0 to 40C.
As coupling components of the formula (3) there may be men-tioned aniline- and 1-aminonaphthalene derivatives which do not contain sulfonic acid groups. These arylamines may be substi-tuted by alkoxy or alkyl groups having from 1 to 4 carbon atomsg by chlorine atoms, or by acetylamino, ben~oylamino and/or tri-~S ~luoromethyl groups. As an example, there may be mentloned:

f~

aniline, o-toluidine, m-toluidi~e, 2,5 a~d 2,6-dimethyla~iline, m-chloroaniline, o- and m-a~isidine, o-- and m-phenetidine, o-and m-n-propylaniline, 2-0thylaniline, m-trifluoromethylani-line, m-acetylaminoanilin~, ami~ohydroquinone-methylether 7

2-methoxy-5-methylaniline 7 m-n-butylaniline 9 1-naphthylamine, 2!-methoxy- and 2-ethoxy-1 naphthylami~e, as well as the sulfa-mic acids and the ~-methylene-sul~onic acids of all compounds mentioned abs~e, i.e.~ for example, compounds corresponding to the formulae:

` H3C , -H-S03H ~ NX-CH~-S03H

~. .
~H-so3~ CO
~ ~ NH-CH~-SO~ I

as well as m-(sulfomethylene-amino)-toluene, 2,5- and 2,6-di-methyl-1-(sulfomethylene-amino)-benzene, a-sulfomethylene-amino)-ethoxy-benzene,1-(sulfomethylene-amino)-2,5-dimethoxy-benzene~ 1-(sulfomethylene-amino)-2-methoxy-5-methyl-benzene, and 1-(sulfomethylene-amino)-naphthalene.
Preference is given to those dyestuf~s o~ the formula(1), in which A represents the phenyle-ne radical optionally substituted by alkoxy groups having from 1 to 4 carbon atoms, such as me-thyl or methoxy group~" by alkyl groups having ~rom 1 to 4 car-bon atom.s1 such as methyl or ~thyl groups 7 by chlorine atoms~

~67896 acetylamino, benzoylamino and/or tri~luoromethyl groups, or represents the naphthylene radical optionally substituted by ethoxy, methoxy, methyl, acetylamino and/or benzoylamino groups, B stands for phenylene optionally substituted by alkyl groups having from 1 to 4 carbon atoms, such as methyl or ethyl groups, and/or alkoxy groups having from 1 ~o 4 carbon atoms, such as methoxy and ethoxy groups, and R is defined as above; of these, the dyestuffs preferred are those compounds, in which A stands for phenylene optionally substituted by chlorine, methyl ethyl, methoxy and/or ethoxy, or represents naph~hlene or methoxy-naphthylene, B stands for the phenylene radical optionally substituted by methyl, methoxy, ethyl and/or ethoxy, and R is defined as above.
Of the dyestuffs of the formula ~1) with one of the above-mentioned definitions of A and B, those dyestuffs are also particularly interesting, in which R represents hydrogen, methyl, ethyl, and ~-hydroxyethyl.
The diazotization of the am-Lnoazo dyestuffs obtained of the general formula (4), in which Z stands for a hydrogen atom or for a sulfonic acid group, is effected according to the common and 2Q known diazotization methods in a strongly acid solution, in which process the`sulfonic acid group is split off during the reaction if compounds of the formula (4) wherein Z is -S03H, are subjected to the diazotization. If compounds of the formula (4) are used in which Z represents -CH2-S03H, an alkaline or acid hydrolysis has to be ef~ected prior to the diazotization at a temperature in the range of from 40 to 100C, and the diazotization of the amine set free by way of the acid hydrolysis may be carried out subsequently H~
g.6 at a tempera~ure in the range o~ from 0 to 15C.
The coupling of the diazonium salts thus obtained o~
th~ aminoazo dyestu~fs o~ the formula (4) with coupling com-ponents ~-B-O~ is carried out at a temperature o~ ~rom 0 t~ 30C ~dar nsutral 'o ~tro.. gl~ al~al5r~e co.,ditior.~ .n th~
pH range of between 6.5 and 12.5, the coupling in the 4-posi-tion to the OH group requires an alkaline medium which is not as strongas that ~or the coupling in the 2-position for which as a rule a pH value o~ approximately 12 is reauired.
The coupling reactions are carried out in known manner by buf-fering or neutralizing the acld diazonium salt solutions or suspensions with alkalis, such as sodlum hydroxide, sodium-or potassium carbonate, by adding the coupling component H-B-OH in its pure ~orm or in the form of an alkaline aqueous solution9 and by subsequently adjusting the optimum pH value ~or the coupling reactionO As coupling compo~ents of the formula H-B-OH there may be mentioned, for example, the follow-; ing compounds: ph~nol, o-, m~ or p-cresol, o~, m- or p-ethyl-phenol, resorclnol, resorc5nol-monomethylether, hydroqui~one-monomethylether 9 2,5-dimethylphenol, 2- and 4-phenylphenol, 2,6-dimethylphenol, 4-isopropylphenol, 4-n-buty~ and 4-ter-t~ry-butylphenol. The dyestu~fs of the general formula (1)in which R stands for the methyl, ethyl, benzenesulfonyl, p-to-luenesulfonyl or p-chlorobenzenesulfonyl radicals~ are ob-tained .from the dyestuffs of the general formula (13 wherein R is hydrogen, by a reaction in an alkaline aqueous solution with dimethgl or diethylsulfate under normal pressure, with methyl or ethyl halides, for example~ methyl or ethyl bromlde, 29 under pressure, with ethylene-oxide or ethylene chlorohydrin HOE 75/F_086 789~;
u~der normal pressure or under pressure, or w~th be~zene-, p-~oluene~.or p-chlorob~ene-sulfochloride under normal pres-sure at a pH value in the range of from 8 to 12 and at a tem~
perature of from 15.to 80C.
T~l~ dyest~ffs o~ tha .~mu a ~1~ accvrdi~g *~ the i~ve~
tion are excellently suitable for the dyeing or printing o~
materials of ~ative and synthetic nitrogen-co~taining ~ibers, especially fibers containing a carbonylamide group~ such as wool and silk, however, preferably of synthetic polyamide and polyurethane fibers from an acid to neutral dye bath at a tem-perature of from 80C to 120C, preferably of about 100~C, in which process use is made of auxiliary agents common in the dye-ing and printing operations. In the dyeing o~ the above-mention-ed materials the dyestuf~s of the invention show a very good color build-up and a good migration capacity and yield level golden-yellow, yellow-brown and orange color 3hades with a good to very good fastness to wetting and a good covering power with regard to the streakiness :in the case o~ polyamide fibers~
which is inherent in this material. The dyeings show a good to excellent fastness to light. Especially in mixtures with other dyestuffs, the reduction o* the ~astness to light having become k~own as the "catalytic fading" effect is only insigni-ficant, as compared against the pure dyestuff.
The following Example~ serve to illustrate the invention.
The parts and -the percentages indicated are "by weight" unless otherwise stated. The parts by weight an~ by volume are in the same rat~o as is the gram to the cubi.c centimeter.
. E X A M P ~ E 1:
29 26.5 Parts of 1-aminobenæene-4-~sulfoethylsulfone sus-67~396 pended in 100 parts ~y volume oî water, were mixed with 50 parts oî ~ ce and 25 parts of h;ydrochloric ~cid OI 31% strength a~d diazotized by the dr~ise addi~ion of 20 parts by volume of a 5N sodium nitrite solutio~. 10.7 Parts o~ o-toluidine di3~0l~ed Wit~l ,2 palt~ Ol c~. h~droc.llo lc ac d '.. 25 pa,ts by volume of water were added to the diazo suspension. A~ter stirring for 1 hour ~he pH value was ad~usted to 3.0 to ~.5 by adding crystalli~e sodium acetate and was maintained 1n this range until the coupling reaction was completed. Sub-sequently the reaction mixture was filtered, and the moist dyestuff was washed with 2~ hydrochloric acid and dissolved with concentrated sodium hydroxide solution in 250 parts by volume of water of 50C; then 20 parts by volume of sodium nitrite solution were added. This solution was then slowly introduced into a mixture o~ 100 parts o~ ice and 25 parts of hydroGhloric acid of 31% strength. After 4- hours the ex-cess nitr~us acid was decomposed with a small amount of ami-dosulfonic acid, and the suspension of the diazo dyestuff wa~ mixed with 10.9 parts of m-cresol. The pH value was ~d-~usted with calcined sodium carbonate to 8.5, was increased to 12 after 2 hours of stirring with a sodium hydroxide so-lution, and was maintained at this leYel for 5 hours. Sub-sequently the reaction mixture was acidiIied with diluted hydrochloric acid up to a pH value of 6.5, the disazo dye-stuff o~ the formula ~l03 5-C~12-CII2-029~ I~===N~ l~r==~ OH

~13 C
_ g _ HOE 7~/F 086 ~ ~67 ~
was separa-ted by adding sodium chloride~ WQS filtered and dried.
The yellow-~rown powder obtained yielded on fibers of polyamide 66 from a neutral or slightl~ acetic bath at a temperature of from 98 to 102C orange dyeings having a high and even depth of 5 ~:h~dl~ ~nd showing ve7~y good 4oC~tn~se propQrtiQs Q to light and wetti~g.
When the above-described dyestuff solution having a p~ value of 12 was mixed with 15 parts by weight of dime-thyl sul~ate, the pH value was reduced to 8.5, after the mixture had been stirred for 2 hours at room temperature, and after a salting-out process with sodium chloride, the dyestu~f of the formula CH
~ H03S-CH2 CH2-2S ~ N===~_ ~ N===N - ~ OCH3 ~3C

was obtained, which yielded under the common dyeing conditions on polyamid2 fib~rs level orange dyeings showing a very good ~astness to light and to wetting.
E ~ A P ~ E 2:
26.5 Parts of 1-aminoben~ene-3-B-sulfoethylsul~one were introduced by stirring into 100 parts by volume of water, then 50 parts of ice and 25 parts of hydrochloric acid o~ 31~ strength were added, and the mixture was diazoti~ed by adding 20 parts by volume o~ 5N sodium nitrite solution~ After 15 minutes, a small amount of excess ~itrous acid was decomposed with a ~e amidosulfonic acid, and a solution of 20.1 par-ts of 3-toluidino-methane-sulfonic acid in 100 parts by volume o~ water was added.
The pH ~alue was maintained in the range o~ from 4.5 to 5.~
by means of calcined sodium carbonate. After the coupling had been completed, sodium hydroxide wa~ added in such an HOE ?5/F ~6 g"~
amount that the solution contained 8% o~ sodium hydroxide. Thealkaline solution was refluxed for 3 hours, was then cooled to room temperature and adjusted to a pH value o~ 1.5 b~ means of hydrochloric acid o~ 31~ strength. The precipitated aminoazo 5 dye~u~î was îiltered OII and was washed WitQ hydr~cnloric acid of 5~ strength.
38.3 Parts (calculated on a 100% dyestuff) of the dry ami~oazo dyestuff were dissolved with concentrated sodium hy~
dro~ide solution in 150 parts by volume of water having a tem-perature of 50C; 20 parts by ~olume of 5N sodium nitrite solu-tion were added. Subsequently the diazo solution was added to a mixture of 100 parts of ice a~d 25 parts of hydrochloric `acid o~ 31% strength. After 3 hours the excess nitrous acid was decomposed with a small amount of amidosulfonic acid, and t5 9 5 parts o~ phenol were added to the diaæo-a~o dyestuff sus-pension. The pH value o~ the coupling mixture was established with a concentrated sodium hydroxide solution first at 9 and after 1 hour at 12 and was maintained at this pH for 3 hours until the dyestuff coupling had been completed~ Subsequently diluted hydrochloric acid ~as added, ~til the pH value was 6.5, and the disazo dyestuff was separated by adding sodium chloride. The d~sazo dyestuf~ obtained had the formula ~SO2 Cl~--CH -~0 H
=

,~....

HOE 7~

~06~396 The yellow-brown powder yi~lded on polycaprolactam fabric from an acetic bath in the presence of the reaction product of 1 mole of stearylamine with 12 moles of ethylene-o~ide as auxi-liary agent at a dyei~g temperature of from 98 to 100C golden-yellow dyeings of a ~ln~form depth nf shad~ W.h~ch shn~A v~r~good fastness properties as to light and to wetting.
When the above-sp~cified dyestuff solution having a pH
value of 12 was mixed with 20 parts of ethylene oxide in 120 parts by volume of water and the reaction mixture was heated : 10 to 40 C, while stirring, the dyestuff of the formula ~===N ~ ~ OCl~2-C~2-o~l C~2C~2-S03 ' was obtained after a reaction of' 4 hours, which dyestuf~ was present as a yellow-brGwn powder after salting-out with sodium chloride and drying. It yielded on wool, ~rom an acetic bath at a temperature of from 98 to 100C, in the presence of the reaction product of 1 mole of stearyl alcohol with 8 moles of ethylene oxide9 a golden-yellow dyeing having very good fast-ness properties as to wetting and light.
E X A M P ~
26.5 Parts of 1-aminobenzene-4-B-sulfoethylsulfone were introduced by stirring into 100 parts by volume o~ water, and 20 part.s hy vol~e of 5N sodlum nitrite solution were added.
The diazo solution was then introduced, while stirring vigo--~2 - .

~r: ' ''!

HOE 7~/F ~6 ~ ~67 ~ ~
rously, i~to ~ mixture of 100 parts of ice and 25 parts o~ h~-drochloric acid of 3~ strength. Af-ter ~0 minutes, a small amount of amido-sulfonic ac~d was added~ and subsequently a solutio~ of 12.1 parts of 2,6 dimethylanili~e and 15 parts of ~ydrochlo~c a^id of 3'~ strer.gth ir~ 75 parts b~ ~r~ ~ma o water was introduced into the mixture. The pH value of the mixture was mai~tained in the range of from 1.8 to 2~0 by means o~ saturat~d sodium acetate solutionO After 9 hours the coup-ling reaction was completed. The dyestuff which had precipi-tated in a crystalline form was suction-filtered and washed with water~ 39.7 Parts o~ the dry aminoazo dyestuff were dis-solved i~ 350 parts by volume o~: water while heati~lg at 70C
; and adding a sodium hydroxide solution of 33% strength~at a pH t~alue of 7.0; then 20 parts by volume of 5~ sod~um nitrite solution were added. Sub6equently this solution was intro-duced into a mixture of 150 parts of ice and 35 parts of hydro-chloric acid of 31% strength, while stirring the mixture vigo-rously. After 6 hours a small amount of amidosulfo~ic acid was added9 and the pH value was adjusted to 6.5 by means of cal-ci~ed sodium carbonate. A solution of 10.8 parts of o-cresol and 12.5 parts of a 33% sodium hydroxide solution in 100 parts by ~olume of water was added to this diazo suspension, and the mixture was stirred at a pH of 12 for 4 hours at room tempera-ture untll the coupli~g reaction was completed. After the p~
ha~ been ad~usted to 6.5 b~ means of diluted hydrochloric acid, the disa~o dyestuff was separa-ted by the addition of sodium chloride and dried. The dyestuff, which was present in the form of a light brown powder, had the formula 67~96 N===N ~ ~ N===N ~ - OH

~H2-CH2-02S CH3 CH3

3~

: When a polyamide fabric was printed with a printing paste con~aining said dyestuff besides conventional printing auxiliary agents, for example, carob bean thickening, an addition product of 8 moles of ethylene oxide to 1 mole of isotridecyl-alcohol and acetic acid, a print having a very good fastness to wetting and to light was obtained after fixation by steaming at a temperature of from 100 to 102C for 6 minutes.
~hen the above-specified dyestuff solution of pH 12 was mixed with 25 parts of p-toluene-sulfochloride and the mixture was stirred at 60C while maintaining a pH in the range of from 11 to 11.5, a dyestuff of the formula HO35-H2C-H2C-o25 ~ N===N ~ N===N ~ O-SO2 ~ CH3 ~as obtained which could be separated after ~ooling the mix-ture and adjus*ing the pH value to 6.5; the dyestuff obtained dyed polyamide carped yarn ~rom a slightly acetic bath in the presence of ammonium acetate and a reaction product of 1 mole of stearylamine with 12 moles of ethylene oxide in orange color shades ~ith a very good fastness to wetting and an excellent HOE 7~F 86 67~9~
fast~ess to light.

2605 Part of 1-aminobenzene-3-~-sul~oethylsulfone were dia~otized as described in Example 2. The diazo suspension obtai~6d wa~ mlxeu -Witil ~ s-usp~nsio~l ul the hrdrocnlori~e of 14.3 parts of 1-naphthylamine in 150 parts by volume of water.
The pH ~alue of the coupling mixture was maintained in the range of ~rom 1.5 to 2.0 by means o~ a sodium acetate solution.
After 8 hours the coupling reaction was completed. The amino-azo dyestu~f was filtered off and was washed with water.
41.9 Parts of the drg monoazo dyestuff were dissolved witha 3~% sodium hydroxide solution in 400 parts by volume of water at a pH value of 7.0 at 90C, and then 20 parts by volume of 5N sodium nitrite solution were added. The diazo suspension was introduced while stirring vigorouslyg into a mixture of 250 parts of ice and 35 parts of a 31~ hydrochloric acid. After 6 hours a small amount of amido~ulfonic acid was added, the pH value of the diazo suspen~ion was adjusted to 6.5~ and a solution of 10.8 parts of p-cre~ol and 12.5 parts of a 33% so-dium hydroxide solution in 100 parts by volume of water wasadded. The mixture was continued to be s~irred for 4 hours at room tempera-ture at a pH value of ~rom 11.0 to 11.5. After 4 hours the coupling was completed; the pE o~ the solution was adjusted to 5.5 with diluted hydrochloric acid, and the disazo dyestuff was separated by adding sodium chloride. The dyestuf~
had the formula HOE 75 jF 0~8~
3i7~

. .
N----N ~ N===N

CH2 - .

and yielded o~ polyamide fibers ~rom an acetic bath at a dye-ing temperature in the range of from 98 to 100C and in the presence o~ common auxiliaries~ such as a reactio~ product of 1 mole of stearyl alcohol and ~ moles of ethylene oxide and a condensation product of 1 mole o~ cyanuric chloride with 3 moles o~ aniline-~-sulfonic acid, level ora~ge dyeings which showed a ~ery good fastness to wetting as well as to l1ght.
When the above-specified;~dyestuff solution having a pH
of 11.0 was mixed with 25 parts o~ diethylsul~ate and the mix-ture was heated 9 while stirring, a~ a temperature in the range of from 40 to 50C, the dyestuff of the ~ormula -N==-~ $ N==-N

~03M - C ~

wa~ obtained after a reaction time of 4 hour~ during which the pH ~alue was maintained~ir3. the range of from 10.0 to 11Ø

HOE 75lF 086 ~678~6 The dyestuff prepared was precipitated completely from t~e aqueous suspensio~ by the addition of sodium chloride and by filtration.
This dyestuff yielded from a neutral dye bath on poly-amide carpet fibers in the presence of a reaction product of ~ 1 mole of stearylamine and 12 moles of ethylene oxide, at a `~ dyeing temperature of from 98 to 100C, an orange dyeing which had ver~ good fastness properties as to wetting and light~

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Claims

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:

1. A water-soluble disazo dyestuff of the general formula (1) (1) in which A represents phenylene or naphthylene which is unsubstituted or sub-stituted by alkoxy of from 1 to 4 carbon atoms, alkyl of from 1 to 4 carbon atoms, chlorine, acetylamino, benzoylamino and/or trifluoromethyl, B stands for the radical of a coupling component of the phenol series, the radical being free from sulfonic acid groups, and R is a hydrogen atom, the methyl, ethyl or .beta.-hydroxyethyl group or the benzene-, p-toluene- or p-chlorobenzene-sulfonyl radical.

2. A water-soluble disazo dyestuff of the formula (1) in which A is phenylene or naphthylene or phenylene or naphthylene substituted by one, two or three substituents selected from the group consisting of alkoxy of 1 to 4 C-atoms, alkyl of 1 to 4 C-atoms, chlorine, acetylamino, benzoylam-ino and trifluoromethyl, B is phenylene or phenylene substituted by one or two substituents selected from the group consisting of alkyl of 1 to 4 C-atoms, alkoxy of 1 to 4 C-atoms, chlorine, phenyl, hydroxy, nitro and bromine, and R
is hydrogen, methyl, ethyl, .beta.-hydroxyethyl, phenylsulfonyl, p-toluyl-sulfonyl or p-chlorophenylsulfonyl.

3. Process for the preparation of a water-soluble disazo dyestuff of the general formula (1) as claimed and defined in claim 1, which comprises diazot-izing a diazo component of the general formula (2) (2) thereafter coupling the diazonium compound with a primary aromatic amine, or with the corresponding sulfamic acid thereof or the corresponding arylamino-methane-sulfonic acid thereof, all of which coupling in the para-position to the amino group and having the general formula (3) H - A - NH - Z (3), in which A is defined in claim 1 and Z stands for a hydrogen atom, a methylene-sulfonic acid group of the formula -CH2-SO3H or for a sulfonic acid group, then diazotizing the aminoazo dyestuff thus obtained which has the general formula (4) (4) wherein A and Z are defined as in claim 1 and above, following a previous al-kaline or acid hydrolytic separation of the methylene-sulfonic acid group if Z stands for -CH2-SO3H, coupling said aminoazo dyestuff with a coupling com-ponent of the formula H-B-OH wherein B is defined as in claim 1, and optionally reacting the disazo dyestuff thereafter in the presence of an acid-binding a-gent at a temperature in the range of from 15 to 80°C or with dimethyl or di-ethyl sulfate or with a methyl or ethyl halide or with ethylene oxide or ethy-lene chlorohydrin, or with benzene-, p-toluene- or p-chlorobenzene-sulfochloride at a pH value of from 8 to 12 and at a temperature in the range of from 15 to 60°C.

4. In a process for the coloration of a material made from native and/or synthetic nitrogen-containing fibers, wherein an acid disazo dyestuff is appli-ed to this material and fixed thereon, the improvement comprising using an acid dyestuff of the formula (1) defined in claim 1.