CA1199632A - Water-soluble disazo compounds - Google Patents
Water-soluble disazo compoundsInfo
- Publication number
- CA1199632A CA1199632A CA000427666A CA427666A CA1199632A CA 1199632 A CA1199632 A CA 1199632A CA 000427666 A CA000427666 A CA 000427666A CA 427666 A CA427666 A CA 427666A CA 1199632 A CA1199632 A CA 1199632A
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- sulfo
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-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/4401—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system
- C09B62/4403—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system the heterocyclic system being a triazine ring
- C09B62/4411—Azo dyes
- C09B62/4415—Disazo or polyazo dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/08—Disazo dyes in which the coupling component is a hydroxy-amino compound
- C09B33/10—Disazo dyes in which the coupling component is a hydroxy-amino compound in which the coupling component is an amino naphthol
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/09—Disazo or polyazo dyes
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- Organic Chemistry (AREA)
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Abstract
ABSTRACT OF THE DISCLOSURE
Water-soluble disazo compounds of the general formula (1) (1) in which R1 and R2, identical to or different from each other, are each a hydrogen atom, an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms or a chlorine atom, R is a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1. to 4 carbon atoms or a sulfo group, M is a hydrogen atom or one equivalent of a metal, X is vinyl or .beta.-sulfatoethyl group, Y is a chlorine atom or a fluorine atom with the proviso that, if Y is chlorine, D is a phenyl radical which can be substituted by 1, 2 or 3 substituents from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, trichloro-methyl, trifluoromethyl, nitro, alkanoylamino having 1 to 4 carbon atoms in the alkyl radical, benzoylamino which can be substituted in the benzene nucleus by one or two substituents from the group consisting of methyl, ethyl, methoxy, ethoxy, chlorine and sulfo, phenylsulfonylamino which can be substituted by one or two sub-stituents from the group consisting of methyl, ethyl, methoxy and ethoxy, carboxy and sulfo, where this phenyl radical D
preferably contains at least one sulfo group or carboxy group as substituent, or D is a naphthyl radical which is substituted by 1, 2 or 3 sulfo groups, and i-f Y is fluorine, D is phenyl unsub-stituted or substituted by 1, 2 or 3 substituents selected from the group consisting of carboxy, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, trichloromethyl, trifluoro-methyl, nitro, alkanoylamino having 1 to 4 carbon atoms in the alkyl moiety, benzoylamino unsubstituted or substituted in the benzene nucleus by 1 or 2 substituents selected from the group consisting of methyl, ethyl, methoxy, ethoxy, chlorine and sulfo, and phenyl-sulfonylamino unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of methyl, ethyl, methoxy and ethoxy, or D is naphthyl substituted by 1, 2 or 3 sulfo groups, and the moieties R1, R2, R, Y and the substituents in D can be identical to or different from one another.
These novel disazo compounds can be prepared analogously to known methods from the components evident from the formula (1) (the aniline compound with the group -SO2-X, the cyanuric halide, the phenylenediaminesulfonic acid, the aminonaphtholdisulfonic acid as bivalent coupling component and the amino compound D-NH2 as second diazo component). They have fiber-reactive dyestuff pro-perties and give on hydroxy- and/or carboxamide-containing material, in particular fiber material, such as cellulosic fibers, strong dyeings having good fastness properties.
Water-soluble disazo compounds of the general formula (1) (1) in which R1 and R2, identical to or different from each other, are each a hydrogen atom, an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms or a chlorine atom, R is a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1. to 4 carbon atoms or a sulfo group, M is a hydrogen atom or one equivalent of a metal, X is vinyl or .beta.-sulfatoethyl group, Y is a chlorine atom or a fluorine atom with the proviso that, if Y is chlorine, D is a phenyl radical which can be substituted by 1, 2 or 3 substituents from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, trichloro-methyl, trifluoromethyl, nitro, alkanoylamino having 1 to 4 carbon atoms in the alkyl radical, benzoylamino which can be substituted in the benzene nucleus by one or two substituents from the group consisting of methyl, ethyl, methoxy, ethoxy, chlorine and sulfo, phenylsulfonylamino which can be substituted by one or two sub-stituents from the group consisting of methyl, ethyl, methoxy and ethoxy, carboxy and sulfo, where this phenyl radical D
preferably contains at least one sulfo group or carboxy group as substituent, or D is a naphthyl radical which is substituted by 1, 2 or 3 sulfo groups, and i-f Y is fluorine, D is phenyl unsub-stituted or substituted by 1, 2 or 3 substituents selected from the group consisting of carboxy, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, trichloromethyl, trifluoro-methyl, nitro, alkanoylamino having 1 to 4 carbon atoms in the alkyl moiety, benzoylamino unsubstituted or substituted in the benzene nucleus by 1 or 2 substituents selected from the group consisting of methyl, ethyl, methoxy, ethoxy, chlorine and sulfo, and phenyl-sulfonylamino unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of methyl, ethyl, methoxy and ethoxy, or D is naphthyl substituted by 1, 2 or 3 sulfo groups, and the moieties R1, R2, R, Y and the substituents in D can be identical to or different from one another.
These novel disazo compounds can be prepared analogously to known methods from the components evident from the formula (1) (the aniline compound with the group -SO2-X, the cyanuric halide, the phenylenediaminesulfonic acid, the aminonaphtholdisulfonic acid as bivalent coupling component and the amino compound D-NH2 as second diazo component). They have fiber-reactive dyestuff pro-perties and give on hydroxy- and/or carboxamide-containing material, in particular fiber material, such as cellulosic fibers, strong dyeings having good fastness properties.
Description
~3363~
The invention relates to the field of fiber-reactive disazo dyestuffs.
with Publication Nos.
European Patent Applications~0,022,265 and 0,048,355 d;sclose f;ber-react;ve dyestuffs which are d;s-azo compounds composed of 1-am;no-8-naphthol-3,6~ or -4,6-d;sulfonic ac;d as bivalent coupling component, an an;l;ne or aminonaphthalene compound acid-coupled thereon as a f;rst diazo component and a phenylenediaminosulfonic acid compound as a second diazo component to whose second amino group is bonded a chloro~riazinyl radical which is bonded to a fiber-reac~;ve aniline radical of the vinyl sulfon~ seriesr W~ have now found novel, valuable and advantageous water-soiuble disazo compounds which hav~ the general formula (13 . ~ S03M ~12N O~I
~ N = N ~ -N ~ ~ - D
R2 ~ Nl ~ N ~ NH ~ M03 ~ S03~i X SO2 (13 in which R is a hydrogen atom, an alkyl group of 1 ~o 4 carbon atoms, such as, for example~ the ethyl group or~ in particular~ the ~ethyl group~ an alk~
oxy group of 1 to 4 carbon a~oms, such as~ for example, the ethoxy grcup orO in particular~ the methoxy group, or a chlorine atom, , ~963~
R is a hydrogen atom, an alkyl group of 1 to 4 carbon atoms, such as, for example, the ethyl group or, in particular, the methyl group, an alkoxy group of 1 to 4 carbon atoms, such as, for example, the ethoxy group or, in particular, the me-thoxy group, or a chlorine atom, and Rl and R2 can be identical to or different from each other, R is a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, such as, for example, the ethyl group or, in particu-lar, the methyl group, an alkoxy group of 1 to 4 carbon atoms, such as, for example, the ethoxy group or, in particular, the methoxy group, or a sulfo group (corresponding to the general formula -S03M where M has the meaning given below), M is a hydrogen atom or an equivalent of a metal, preferably of a monovalent or divalent metal, such as of an alkali or alkaline earth metal, in particular of sodium, potassium or calcium, X is vinyl or ~-sulfatoethyl group, Y is a chlorine atom or a fluorine atom with the proviso that if Y is chlorine, D is a phenyl radical which can be substi-tuted by 1, 2 or 3 substituents from the group consistlng of carboxy, (corresponding to the general formula -COOM where M is of the above-mentioned meaning) sulfo, alkyl of 1 to 4 carbon atoms, 2Q such as ethyl or, in particular, methyl, alkoxy of 1 to 4 carbon atoms, such as ethoxy or, in particular, methoxy, halogen, such as chlorine, bromine or fluorine, trichloromethyl, trifluoromethyl, nitro, alkanoylamino having 1 to 4 carbon atoms in the alkyl radical, such as acetylamino or propionylamino, benzoylamino which can be substituted in the ben~ene nucleus by one or two sub-stituents from the group consisting of methyl, ethyl, methoxy, ethoxy, chlorine and sulfo, phenylsulfonylamino which can be substituted in the phenyl radical by one or two substituents ,-r~
;? ., ~ -- 3 ~963~
from the group consisting of methyl, ethyl, methoxy and ethoxy, such as p-toluenesulfonylamino, and this phenyl radical D prefer-ably contains as substituent at least one sulfo group or carboxy group, or D is a naphthyl radical which is substituted by 1, 2 or 3 sulfo groups, and if Y is fluorine, D is phenyl unsubstituted or substituted by 1, 2 or 3 substituents selected from the group consisting of carboxy, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, trichloromethyl, tri.fluoromethyl, nitro, alkanoylamino having 1 to 4 carbon atoms in the alkyl moiety, benzoylamino unsubstituted or substituted in the benzene nucleus by 1 or 2 substituents selected from the group consisting of methyl, ethyl, methoxy, ethoxy, chlorine and sulfo, and phenylsulfonylamino unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of methyl, ethyl, methoxy and ethoxy, or D is naphthyl substituted by 1, 2 or 3 sulfo groups, provided that in compounds in which the triazinyl-amino radical is bonded to the benzene nucleus in the meta-position to the azo group and in the para-position to the sulfo group -SO3M and R is hydrogen, then D is not 5-sulfo-naphth-1-yl, 1,5-disulfo-naphth-2-yl, 4,8-disulfo-naphth-2-yl, l-sulfo-naphth-
The invention relates to the field of fiber-reactive disazo dyestuffs.
with Publication Nos.
European Patent Applications~0,022,265 and 0,048,355 d;sclose f;ber-react;ve dyestuffs which are d;s-azo compounds composed of 1-am;no-8-naphthol-3,6~ or -4,6-d;sulfonic ac;d as bivalent coupling component, an an;l;ne or aminonaphthalene compound acid-coupled thereon as a f;rst diazo component and a phenylenediaminosulfonic acid compound as a second diazo component to whose second amino group is bonded a chloro~riazinyl radical which is bonded to a fiber-reac~;ve aniline radical of the vinyl sulfon~ seriesr W~ have now found novel, valuable and advantageous water-soiuble disazo compounds which hav~ the general formula (13 . ~ S03M ~12N O~I
~ N = N ~ -N ~ ~ - D
R2 ~ Nl ~ N ~ NH ~ M03 ~ S03~i X SO2 (13 in which R is a hydrogen atom, an alkyl group of 1 ~o 4 carbon atoms, such as, for example~ the ethyl group or~ in particular~ the ~ethyl group~ an alk~
oxy group of 1 to 4 carbon a~oms, such as~ for example, the ethoxy grcup orO in particular~ the methoxy group, or a chlorine atom, , ~963~
R is a hydrogen atom, an alkyl group of 1 to 4 carbon atoms, such as, for example, the ethyl group or, in particular, the methyl group, an alkoxy group of 1 to 4 carbon atoms, such as, for example, the ethoxy group or, in particular, the me-thoxy group, or a chlorine atom, and Rl and R2 can be identical to or different from each other, R is a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, such as, for example, the ethyl group or, in particu-lar, the methyl group, an alkoxy group of 1 to 4 carbon atoms, such as, for example, the ethoxy group or, in particular, the methoxy group, or a sulfo group (corresponding to the general formula -S03M where M has the meaning given below), M is a hydrogen atom or an equivalent of a metal, preferably of a monovalent or divalent metal, such as of an alkali or alkaline earth metal, in particular of sodium, potassium or calcium, X is vinyl or ~-sulfatoethyl group, Y is a chlorine atom or a fluorine atom with the proviso that if Y is chlorine, D is a phenyl radical which can be substi-tuted by 1, 2 or 3 substituents from the group consistlng of carboxy, (corresponding to the general formula -COOM where M is of the above-mentioned meaning) sulfo, alkyl of 1 to 4 carbon atoms, 2Q such as ethyl or, in particular, methyl, alkoxy of 1 to 4 carbon atoms, such as ethoxy or, in particular, methoxy, halogen, such as chlorine, bromine or fluorine, trichloromethyl, trifluoromethyl, nitro, alkanoylamino having 1 to 4 carbon atoms in the alkyl radical, such as acetylamino or propionylamino, benzoylamino which can be substituted in the ben~ene nucleus by one or two sub-stituents from the group consisting of methyl, ethyl, methoxy, ethoxy, chlorine and sulfo, phenylsulfonylamino which can be substituted in the phenyl radical by one or two substituents ,-r~
;? ., ~ -- 3 ~963~
from the group consisting of methyl, ethyl, methoxy and ethoxy, such as p-toluenesulfonylamino, and this phenyl radical D prefer-ably contains as substituent at least one sulfo group or carboxy group, or D is a naphthyl radical which is substituted by 1, 2 or 3 sulfo groups, and if Y is fluorine, D is phenyl unsubstituted or substituted by 1, 2 or 3 substituents selected from the group consisting of carboxy, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, trichloromethyl, tri.fluoromethyl, nitro, alkanoylamino having 1 to 4 carbon atoms in the alkyl moiety, benzoylamino unsubstituted or substituted in the benzene nucleus by 1 or 2 substituents selected from the group consisting of methyl, ethyl, methoxy, ethoxy, chlorine and sulfo, and phenylsulfonylamino unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of methyl, ethyl, methoxy and ethoxy, or D is naphthyl substituted by 1, 2 or 3 sulfo groups, provided that in compounds in which the triazinyl-amino radical is bonded to the benzene nucleus in the meta-position to the azo group and in the para-position to the sulfo group -SO3M and R is hydrogen, then D is not 5-sulfo-naphth-1-yl, 1,5-disulfo-naphth-2-yl, 4,8-disulfo-naphth-2-yl, l-sulfo-naphth-
2-yl nor 3,6,8-trisu].fo-naphth-2-yl.
The above moieties (Rl, R2, R, Y and the substituents in D) can be identical to or different from one another.
A preferred embodiment of the present invention is a water-soluble disazo compound of the formula 11) ~ - 4 -63~
R~ SO3M H2N OH
\,~ ¦l ~ N = N~N=N-D
R2 ~ NHJ~ ~ NH~ ~ SO3M
X-S02 (1) in which R and R , identical to or different from each other, are each a hydrogen atom, an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms or a chlorine atom, R is a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms or a sulfo group, M is a hydrogen atom or the equivalent of a metal, X is vinyl or ~-sulfatoethyl group, Y is a chlorine atom or a fluorine atom with the proviso that, if Y is chlorine, D is a phenyl radical which can be substituted by 1, 2 or 3 substituents from the group con-sisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, trichloromethyl, trifluoromethyl, nitro, alkanoylamino having 1 to 4 carbon atoms in the alkyl radical, benzoylamino which can be substituted in the benzene nucleus by one or two substituents from the group consisting of methyl, ethyl, methoxy, ethoxy, chlorine and sulfo, phenylsulfonylamino which can be substituted by one or two substituents from the group consisting of methyl, ethyl, methoxy and ethoxy, carboxy and sulfo, or D is a naphthyl radical which is substituted by 1, 2 or 3 sulfo groups, if Y is fluorine, D is monosulfophenyl or is naphthyl substituted by 1, 2 or 3 sulfo groups and the moieties Rl, R2, R, Y and the substituents in D can be identical - 4a -! y~
~' ~
to or different from one another.
The azo compounds of the invention can be in the form of their free acid or preferably in the forrn of their salts, in particular neutral salts; specific examples of such salts are the alkali metal and alkaline earth metal salts, for example the sodium, potassium or calcium salts. The new compounds are preferably used in the form of these salts for dyeing lin the general sense and including 4b -~ q~
printing~ hydroxy- and/or carboxamide-containing material, in particular fiber material~
The presen~ invention also relates to a process for preparing these disazo compounds of the invention, which comprises coupling a monoazo compound of the general formula (2) 2~ H ~ so M
X-SO
~ (2) in which R1, R2, R, D, M, Y and X have the abovementioned ~eanings, with ~he diazonium salt of an am;no compound o-f the general formula (3) ~ l2N - D ~3) ;n which D has the abovementioned meaning.
The coupling reaction in the process of the inven-tion is carried ou~ analogously to known methods, for example in an aqueous medium at a pH-value between
The above moieties (Rl, R2, R, Y and the substituents in D) can be identical to or different from one another.
A preferred embodiment of the present invention is a water-soluble disazo compound of the formula 11) ~ - 4 -63~
R~ SO3M H2N OH
\,~ ¦l ~ N = N~N=N-D
R2 ~ NHJ~ ~ NH~ ~ SO3M
X-S02 (1) in which R and R , identical to or different from each other, are each a hydrogen atom, an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms or a chlorine atom, R is a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms or a sulfo group, M is a hydrogen atom or the equivalent of a metal, X is vinyl or ~-sulfatoethyl group, Y is a chlorine atom or a fluorine atom with the proviso that, if Y is chlorine, D is a phenyl radical which can be substituted by 1, 2 or 3 substituents from the group con-sisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, trichloromethyl, trifluoromethyl, nitro, alkanoylamino having 1 to 4 carbon atoms in the alkyl radical, benzoylamino which can be substituted in the benzene nucleus by one or two substituents from the group consisting of methyl, ethyl, methoxy, ethoxy, chlorine and sulfo, phenylsulfonylamino which can be substituted by one or two substituents from the group consisting of methyl, ethyl, methoxy and ethoxy, carboxy and sulfo, or D is a naphthyl radical which is substituted by 1, 2 or 3 sulfo groups, if Y is fluorine, D is monosulfophenyl or is naphthyl substituted by 1, 2 or 3 sulfo groups and the moieties Rl, R2, R, Y and the substituents in D can be identical - 4a -! y~
~' ~
to or different from one another.
The azo compounds of the invention can be in the form of their free acid or preferably in the forrn of their salts, in particular neutral salts; specific examples of such salts are the alkali metal and alkaline earth metal salts, for example the sodium, potassium or calcium salts. The new compounds are preferably used in the form of these salts for dyeing lin the general sense and including 4b -~ q~
printing~ hydroxy- and/or carboxamide-containing material, in particular fiber material~
The presen~ invention also relates to a process for preparing these disazo compounds of the invention, which comprises coupling a monoazo compound of the general formula (2) 2~ H ~ so M
X-SO
~ (2) in which R1, R2, R, D, M, Y and X have the abovementioned ~eanings, with ~he diazonium salt of an am;no compound o-f the general formula (3) ~ l2N - D ~3) ;n which D has the abovementioned meaning.
The coupling reaction in the process of the inven-tion is carried ou~ analogously to known methods, for example in an aqueous medium at a pH-value between
3 and 9, preferably at a pH-value between ~ a-~d 7.
The monoa~o compound of the general formula (2~, which is used as a starting compound, can be prepared ;n a manner of the invention by reacting ~he diazon;um salt 2n of an amino compound of the general formula (4) ~2 ~ NH ~ N ~ NH- ~ NH2 X-S02 ' ~ j 63~
~ 6 --in which R1, R2, R, M, Y and X have the abovementioned meanings with 1 amino-8-naphthol-3,6- or -4,6-disuLfonic ac;d in an acid, preferably aqueous, medium, for example at pH 0 - 3. The d;azotization of the amine of the general formula (4) and the acid coupling reaction can be carried out analogously to long known methods.
Amino compounds of the general formula (4~, which are used as starting materials, can be prepared analog-ously to known methods, described, for example, inwith Publication Nos.
European Patent Applications~0,032,187, 0,036,133, 0~036,582 and 0,0~0,806, by reacting cyanuric chloride or cyanuric fluoride (2,4,6-tr;chloro- or 2,4,6-trifluoro-1,3,5-triazine? f;rst with 3n amino compound of the gene-ra( formula (5) 1?.1 , ~2~3 N~12 ;n which R1, R2 and X have the abovementioned meanings, and then with a phenylened;amino compound of the general formula (6?
~ (6 R
20 ;n wh;ch M and R have the abovementioned meanings~
For example, the reaction of the cyanuric chloride in the first condensation s~age with the amine of the general fornula (5) can be carried out in an aqueous an medium or aqueous organic medium in the presence of~acid acceptor, such as alkali metal or alkal;ne earth metal S carbonates, alkal; metal or alkal;ne earth metaL hydro-gencarbonates or hydrox;des or alkal; metal acetates - the alkal; and alkaline earth metals preferably being sodium, potassium or calcium -, and similarly of, for example, tertiary amines, such as pyridine, triethylamine or quino-10 line. The reaction te~perature chosen for preparing thisprimary condensation product ;s within the range between -10C and ~40C, preferably between -10C and +30C, ;n particular preferably between 0C andt10C, at a pH of from 0.7 ~0 5, preferabLy .1 to 3.
The second condensation stage, between the di-chlorotriazinylamino compound and the phenylenediamino compound of the general formula (6), can also be carried out ;n an aqueous organic medium; but it ;s preferably carr;ed out ;n an aqueous medium to which, if necessary, an acid acceptor~ like those given above, is added~ The reaction temperature is preferably chosen from between 10 and 60C, part;cularly preferably between Z0 and 50C, at a pH of from 2 to 8, in particular of from 3 to 6.
The reaction of cyanuric fluoride in the first condensation stage w;th the amino compound of the general formula (6) is carried out analogou~ly to that of cyanuric chloride, but preferably in an aqueous organic med;um at a ~emperature between -10C and +20C, in particular be~een .. . . , .. _ _ ~
0C and t10C, at a pH of from 0.7 to 3, pr.eferabiy or f~o~ 1 to 2.
. _ _ _ _ .... . . . _ . . . _ ... . .. . .. . . .
Like the dichlorotriazinylamino compound, the difluoro-~riazinylamino compound from cyanuric fluoride and the amino compound of the general formula (S~ can also be reacted with phenylened;amino compound of the general for-mula (6), preferably at a reaction temperature be~Jeen 0C and -~30C, in particular between 10C and 20C, at a pH
of from 2 to 6, pre~erably of from 4 to 5. The~amin~ compounds of the formulae (5) and (6) can, however, also be reacted in reverse order with cyanuric chloride or cyanuric fluor-ide, to give conpounds of the formula (4).
An example of an organic solvent which can be usedin these condensation reactions is acetone in which the cyanuric chloride or cyanuric fluoride has been d;ssolved beforehand; however, it is also possible to d;spense ~ith organic solvents.
Examples of amino compounds of the general formula (3) which can be used as starting compounds in the pre-parat;on of d;sazo compounds according to the invention are ~-chloroaniline, 2,4-d;chloroaniline~ 2-carboxyan;line, 3-carboxyaniline, 4-chloroaniline-2~sulfonic ac;d, 2-chloroaniline-4-sulfonic acid, 6-chloro-3-aminotoluene-~-sulfonic acid, 2,5-d;chloroaniline-4 sulfonic acid, 2~5-dimethoxyaniline-4-sulfonic acid~ 4-ni~roaniline, 4~
acetylaminoanil;ne-2-sulfonic acid and 3-acetylaminoani-line-6-sulfonic acid and preferably aniline-2-sulfonic ac;dO aniline-4-sulfonic ac;d, an;line-2~4-disulfon;c acid and aniline-2,5-disulfonic ac;d~ and among naphthyl-amines, for example9 1-aminonaphthalene 4-sulfonic acid~
2-aminonaphthalene-5 sulfonic acid~ 2 aminonaph~halene~
6~
g 6-sulfonic acid, Z-aminonaphthalene-7-sulfonic acid, 2-aminonaphtllalene-3,6~disulfonic acid, 2-aminonaphthalene-
The monoa~o compound of the general formula (2~, which is used as a starting compound, can be prepared ;n a manner of the invention by reacting ~he diazon;um salt 2n of an amino compound of the general formula (4) ~2 ~ NH ~ N ~ NH- ~ NH2 X-S02 ' ~ j 63~
~ 6 --in which R1, R2, R, M, Y and X have the abovementioned meanings with 1 amino-8-naphthol-3,6- or -4,6-disuLfonic ac;d in an acid, preferably aqueous, medium, for example at pH 0 - 3. The d;azotization of the amine of the general formula (4) and the acid coupling reaction can be carried out analogously to long known methods.
Amino compounds of the general formula (4~, which are used as starting materials, can be prepared analog-ously to known methods, described, for example, inwith Publication Nos.
European Patent Applications~0,032,187, 0,036,133, 0~036,582 and 0,0~0,806, by reacting cyanuric chloride or cyanuric fluoride (2,4,6-tr;chloro- or 2,4,6-trifluoro-1,3,5-triazine? f;rst with 3n amino compound of the gene-ra( formula (5) 1?.1 , ~2~3 N~12 ;n which R1, R2 and X have the abovementioned meanings, and then with a phenylened;amino compound of the general formula (6?
~ (6 R
20 ;n wh;ch M and R have the abovementioned meanings~
For example, the reaction of the cyanuric chloride in the first condensation s~age with the amine of the general fornula (5) can be carried out in an aqueous an medium or aqueous organic medium in the presence of~acid acceptor, such as alkali metal or alkal;ne earth metal S carbonates, alkal; metal or alkal;ne earth metaL hydro-gencarbonates or hydrox;des or alkal; metal acetates - the alkal; and alkaline earth metals preferably being sodium, potassium or calcium -, and similarly of, for example, tertiary amines, such as pyridine, triethylamine or quino-10 line. The reaction te~perature chosen for preparing thisprimary condensation product ;s within the range between -10C and ~40C, preferably between -10C and +30C, ;n particular preferably between 0C andt10C, at a pH of from 0.7 ~0 5, preferabLy .1 to 3.
The second condensation stage, between the di-chlorotriazinylamino compound and the phenylenediamino compound of the general formula (6), can also be carried out ;n an aqueous organic medium; but it ;s preferably carr;ed out ;n an aqueous medium to which, if necessary, an acid acceptor~ like those given above, is added~ The reaction temperature is preferably chosen from between 10 and 60C, part;cularly preferably between Z0 and 50C, at a pH of from 2 to 8, in particular of from 3 to 6.
The reaction of cyanuric fluoride in the first condensation stage w;th the amino compound of the general formula (6) is carried out analogou~ly to that of cyanuric chloride, but preferably in an aqueous organic med;um at a ~emperature between -10C and +20C, in particular be~een .. . . , .. _ _ ~
0C and t10C, at a pH of from 0.7 to 3, pr.eferabiy or f~o~ 1 to 2.
. _ _ _ _ .... . . . _ . . . _ ... . .. . .. . . .
Like the dichlorotriazinylamino compound, the difluoro-~riazinylamino compound from cyanuric fluoride and the amino compound of the general formula (S~ can also be reacted with phenylened;amino compound of the general for-mula (6), preferably at a reaction temperature be~Jeen 0C and -~30C, in particular between 10C and 20C, at a pH
of from 2 to 6, pre~erably of from 4 to 5. The~amin~ compounds of the formulae (5) and (6) can, however, also be reacted in reverse order with cyanuric chloride or cyanuric fluor-ide, to give conpounds of the formula (4).
An example of an organic solvent which can be usedin these condensation reactions is acetone in which the cyanuric chloride or cyanuric fluoride has been d;ssolved beforehand; however, it is also possible to d;spense ~ith organic solvents.
Examples of amino compounds of the general formula (3) which can be used as starting compounds in the pre-parat;on of d;sazo compounds according to the invention are ~-chloroaniline, 2,4-d;chloroaniline~ 2-carboxyan;line, 3-carboxyaniline, 4-chloroaniline-2~sulfonic ac;d, 2-chloroaniline-4-sulfonic acid, 6-chloro-3-aminotoluene-~-sulfonic acid, 2,5-d;chloroaniline-4 sulfonic acid, 2~5-dimethoxyaniline-4-sulfonic acid~ 4-ni~roaniline, 4~
acetylaminoanil;ne-2-sulfonic acid and 3-acetylaminoani-line-6-sulfonic acid and preferably aniline-2-sulfonic ac;dO aniline-4-sulfonic ac;d, an;line-2~4-disulfon;c acid and aniline-2,5-disulfonic ac;d~ and among naphthyl-amines, for example9 1-aminonaphthalene 4-sulfonic acid~
2-aminonaphthalene-5 sulfonic acid~ 2 aminonaph~halene~
6~
g 6-sulfonic acid, Z-aminonaphthalene-7-sulfonic acid, 2-aminonaphtllalene-3,6~disulfonic acid, 2-aminonaphthalene-
4,8-disulfonic ac;d and 2-am;nonaphthalene-3,6,~-tr;sul-fon;c acid and preferably 2-aminonaphthalene-1-sulfonic
5 acid and 2-aminonaphthalene-1,5-disulfon;c acid.
Examples of amino compounds of the general for-~ula (5) are 3-(~-sulfatoethylsulfonyl)-aniline, 3-vinyl-sulfonylaniline, 2-methoxy-5-(~-sulfatoethylsulfonyl)~
aniline, 2-methoxy-5-vinylsulfonylaniline, 2,5-dimethoxy-10 4 (~-sulfatoethylsulfonyl)-aniline and ;ts vinylsulfonyl derivative, 2-me~hoxy-4-(~-sulfatoethylsulfonyl)-aniline and its vinylsulfonyl derivative, 4-methoxy-5-(~-sulfato-ethylsulfonyl)-aniline and its vinylsulfonyl derivative, 2,4-dimethoxy-5-~-sulfatoethylsulfonylaniline and its 1~ vinylsulfonyl derivative, 2-methoxy-5-methyl-4-(~-sulfato-ethylsulfonyl)-anil;ne and ;ts v;nylsulfonyl derivative, 2-methoxy-5-chloro-4-(~-sulfatoethylsulfonyl)-aniline and its vinylsulfonyl derivative, but preferably 4-(~-sulfato-ethylsulfonyl)-aniline and 4-vinylsulfonylaniline.
Examples of phenylenediamino compounds of the general formula ~6) are 1,4-diaminobenzene-2,5-disulfonic acid, 1,4~diaminobenzene-2,6-disulfonic acid, 2,5-diamino~
toluene-4-sulfonic acid, 2~4-diaminotoluene-5 sulfonic acid, 2,5~diaminoanisole-4-sulfon;c acid and 2,4 d;amino-anisole-5~sulfon;c acid~ but preferably 1~3-d;aminobenzene-4-sulfonic acid and 1,4-diaminobenzene-5-sulfonic acid~
Those compounds of the invention are preferred in which ~he group of the formula ~S02-X is bonded to the benzene nucleus in meta-position, ;n part;cular in para-position, relat;ve to the am;no group. ~hose compounds of the invention are also preferred in wh;ch the moiety X represents the ~-sulfatoethyl group.
Moreover, ;n disazo compounds of the general for-mula (1), the moiety R1 is pre~erably a hydrogen atomor a methyl group or a methoxy group or a chlorine atom, R2 is preferably a hydrogen atom, a methyl group or a methoxy group and R is preferably a hydrogen a~om or a sul-fo group.
1~ Furthermore, in compounds of the ;nvention, the moiety D is preferably a phenyl rad;cal which ;s substi-tuted by one, two or three substituents which are sel-ected from the group cons;sting of 2 alkoxy groups of 1 to 4 carbon atoms, 2 alkyl groups of 1 to 4 carbon atoms, 2 chlorine atoms~ 1 bromine atom, 1 fluorine atom~ 1 tri~
chloromethyl group, 1 trifluoromethyl group~ 1 alkanoyl a~;no group having 1 to ~ carbon atoms in the alkyl rad;-cal, 1 n;tro group, 1 carboxy group and 2 sulfo groups.
D ;s part;cularly preferably the phenyl rad;cal wh;ch is substituted by 1, 2 or 3 substituents selected from the group consist;ng of 2 alkoxy groups, such as, in part;cu-lar, me~hoxy groups, 2 chlorine atoms, 2 sulfo groups, 1 carboxyl group, 1 nitro group, 1 alkyl group of 1 ~o 4 carbon atoms, such as, in particular, a Methyl group, and 1 acetylam;no group. D ;s ir, par~;cular a phenyl rad;ca~
wh;ch is subst;tuted by one or two sulfo 0roups.
D is also preferably a naphthyl radical whish ;s subst~tuted by 1, 2 or 3 sulfo groups~
No~eworthy ind;vidual compounds are espesially 96~
the novel disazo cornpounds descr;bed in Examples 1 to 9, 13, 17, 19 and 20~
Compounds of the ~eneral -formula (1) prepared according to the invention can be separated and isolated 5 from the synthesis solutions by generally known methods, for example by precipitating them from the reaction medium by means of electrolytes~ such as, for example, sodium chloride or potassium chloride, or by evapora~ing, for example spray~drying~ the reaction solution, to which a 10 buffer substance, such as, for example, a rnixture of monosodium and disodium phosphates can be added. If appro-priate, ~hese synthesis solutions, if necessary after a buffer substance has been added and/or they have been con-centrated, can also be used in dyeing directly as a liquid 15 formulat;on.
D;sazo compounds of the ;nvent;on have valuable dyestuff properties which~ by virtue of the v;nylsulfonyl or ~-sulfatoethylsulfonyl group and the halogenotriazinyl radical, have fiber-reactive properties~ The new com-20 pounds are preferably used for dyeing ~in the generalsense as ;nclud;ng print;ng) llydroxy- and/or carboxalnide~
containing mater;als, for example in the fc,rm of ~heet-l;ke struc~ures, such as paper and leather or sheeting, such as, for example, made of polyamide, or in the mass, 25 such as, for example, polyamide and polyurethane, but in particular these ma~erials in fiber form~ ~he presen~
invention accordingly also relates to the use of co~pounds o~ the general formula (1) for dyeing ~in the above sense~
these materials or rather to methods for dyeing such materials in conventional methods ;n which a compound of the general formula t1) ;s used as a coloran~ In these methods the materials are preferably ;n the form of f;ber mater;als, ;n particular in the form of textile fibers, 5 such as yarns, packages, or woven or knitted fabr;cs.
~ Iydroxy ~containin~ materials are natural, regen-erated or synthetic hydroxy -containing materials, such as, for example, cellulose fiber mater;als or regenera~ed cellulos;c mater;als or polyvinyl alcohols. Cellulose f;ber materials are preferably cottonr but also other vege~able fibers, such as linen, hemp~ jute or ram;e fibers; examples of regenerated cellulose f;bers are v;s-c~se staple and filament v;scose~
Examples of carboxam;de-con~a;n;ng mater;als are synthet;c nylons, such as nylon ~,6, nylon 6, nylon 11 or nylon ~, and polyurethanes, ;n part;cular ;n the form of f;bers, or natural polyam;des, for example wool or other an;mal ha;rs, s;lk or leather.
D;saz.o compounds of the ;nvent;on can be applied and f;xed to sa;d substrates, ;n part;cular to sa;d f;ber mater;als, by the appl;cat;on techniques known for water-soluble dyestuffs, ;n particular for fiber-react;ve dye-stuffs~ .
~or ;nstance, on cellulose f;bers they g;ve ;n the exhaus~ me~hod in ~he presence of various ac;d accep-tors and, if desired~ neutral salts, such as sodium chlor~
idè or sodium sulfate, very good color yields and excel-lent color bu;ld~upn Dye;ng ;s carried out at ~empera-tures between ~ and 105C~ preferably bet~Jeen 60 and : ' a~;3~
100C, ;f appropr;ate at temperatures up to 120C under pressure, ;f appropr;ate in the presence of customary dye;ng aux;Liaries~ in an aqueous bath, by ;ntroduc;ng the fiber material into a warm bath and gradually raising 5 this to the desired dyeing temperature and complet;ng the dye;ng process at this temperature~ If desired, neutral salts which accelerate the exhaus~ion of the dyestuff can also be added to the bath only after the dyeing tempera-ture proper has been reached~
The padding method also gives excellent color y;elds on cellulosic fibers, on wh;ch the dyes can be fixed ;n a customary manner by leaving the dyeing to stand at room temperature or elevated temperature, for example up to 60C, by steam;n3 or by means of dry heat~
S~rong pr;nts hav;ng well-delineated contours and ~ a clear white ground are also obtained in customary print-: ing methods for cellulosic fibers~ which can be carried out in one step - for example by printing with a print paste containing sodium bicarbonate or a d;fferent ac;d-b;nd;ng agent and then steaming at 100 bo 103C - or ~h'O
steps - for example by printing wi~h a neutral or weakly acid print paste and then fix;ng either by passing the printed goods through a hot electrolyte-conta;ning alkal-ine bath or by overpadding w;th an alkal;ne electrolyte-conta;ning padd;ng liquor and then leaving the material : overpadded to stand or steaming it or ~reating ;t with dry heat. ~ The ou~come of the prin~s is hardly depen-:; dent on varying fix;ng conditions, if at all~ The .. degrees of fixation obtained with the compounds o-f the .. ..
;nvention not only in dye;ng but also ;n pr;nt;ng are very h;gh~
In add;tion to customary steam at 100to 103C, ;t is also poss;ble to use superheated steam or saturated 5 steam at temperatures of up to 160Ca In dry heat f;xing by customary thermof;x;ng methods, hot air at 120 to 200C
is used.
Examples of the agents which bind acid and effect the fixat;on of compounds of the invention on celLulosic 10 fibers are water-soluble basic salts of alkali metals and also alkaline earth metals of inorganic or organic acids or compounds which liberate alkali when heated. The alkali metal hydroxides and aLkali metal salts of ~leak to medium inorganic or organic acids are particularly 15 noteworthy, the sodium and potassium compounds being intended ;n particular among the alkal; metal compounds.
Examples o, such acid-b;nding agents are sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, sodium formate, sodium dihydrogen-20 phosphate, d;sod;um hydroQenphosphate, sod;um tr;chloro-acetate, sod;um s;l;cate and tr;sod;um phosphate.
The treatment of compounds of the invention with acid bind;ng agencs, if appropriate under heat~ bonds ~he compounds of the invent;on chem;cally to the cellulose 25 fiber. The cellulose dyeings, ;n particular, have excel-len~ manufacturing and end~use fastness propercies, such as~ in parti~ular, wet fastness propert;es, after the cus tomary aftertreatmen~ whereby unf;xed dyestuff portions are removed by rinsing~
~ 15 -As regards the coloristic properties of compounds according to the invention, ;t is particularly note~orthy that they are distinguished by good stability in print pastes and padding liquors, even in the presence of alka-S lis, by very good a~finity from a long liquor, by goodcoLor build-up in customary dyeinQ and printing methods, by an even depth of shade in the dyeing of cotton and regenerated cellulose f;bers, by the levelness of the dye-;ngs and prints prepared with them and also by the fact 1D that long l;quor dyeings are level i~ various amounts of electrolyte have been added. Unfixed dyestuff portions can be readily washed out.
Polyurethane fibers and polyamide fibers are cus-tomarily dyed from an ac;d med;um. ~or example, acet;c ac;d and/or ammon;um sulfate or acet;c acid and ammonium acetate or sodium acetate can be added to the dyeba~h to obtain the desired pH. To obtain an acceptably level dyeing, it is advisable to add customary level;ng auxili-aries~ such as, for e~ample, those based on a reaction product of cyanur;c chlor;de w;th three t;mes the molar amount of an am;nobenzenesulfonic ac;d and/or an am;no-naphthalenesulfonic acid or ~hose based on a react;on pro-duct of, for example, stearylamine with ethylene oxide~
The material to be dyed is generally ;ntroduced at a tem-~5 perature of about 40C into the initially slightly alka-line bath, and ag;tated there;n for some t;me, the dye bath ;s brought to a weakly ac;d~ preferably weakly ace-tic ac;d pH, and the actual dyeing is carr;ed out at a temperature between 30 and 105C~ pre~erably between ~0 and 100Cn Disazo compounds of the ;nvention are distin-guished in the dyeing and printing of fiber materials by a high degree of fixation, ~hich fact is economically, 5 energyw;se and ecologically of great benefit in ;ndustry, since a h;gh ut;l;zation of the dyestuff offered by a higher f ~ tion mgans an energy saving and easier washiny-out of the~reduc~d)unfixed dyestuff portion~and additionally the effluent is less polluted.
Dyeings and prints prepared ~ith disazo compounds of the formula ~1~ are d;stinguished by bright shades.
The dyeings and prints on cellulosic fiber mater;als, in part;cular, have, as already mentioned, a great tinctorial strength and, furthermore, very good light fastness pro-15 perties(not only in the dry but also in the moist stat~, and very good fast~esses to was~ing with both peroxide-free and peroxide containin~ detergents, to milling~ toand water A sea~ater,and acid fastness properties, and also very good crossdyeing fastness properties, such as, in 20 particular, very good acid crossdyeing fastness properties, and very good persp;ration fastness properties, and also good pleat;ng, hs~ pressing~ rubb;ng and gas fume fading fastness properties~ They are also highly resistant ~o chlorina~ed ~ater and copper ion donors; they are there-25 fore compatible~ for example~ ~ith copper complex dye-stuffs. Nor does ~he use of compounds of the invention in dyeing cellulosic fiber ma~erials harden the hand of the dyed material.
Neither print pastes, nor padd;n~ l;quors~ nor f C~ 17 -dye;n~ liquors nor unfixed prin~s or pad-dyeings wi~h com~
pounds of the invention are sensi~ive to gases which are acid or contain sulfur dioxide~
Dyeings prepared with compounds of the invention S have navy to black shades; they generally do not exh;bit in art;fic;al l;ght the unfavorable, undesirable reddish tinge which leads to the 'red even;ng shade~ since they generally have a sl;ghtLy more green;sh t;nge. Fr,r th;s reason the compounds of the invent;on generally have a 10 llneutral~evening shade, so that ;t is not necessary to blend the disazo compounds of che ;nvent;on w;th a su;t-able shading dyestuff; for dyestuffs which exper;ence a marked sh;ft in hue under art;ficial light have the disad-vantage that it not only restr;cts their general suit-abil;ty for prepar;ng dye;ngs but also complicates theiruse in the preparation of dyeings when shad;ng dyestuffs have to be added to obta;n dyeings which are reasonably satisfac~ory when exposed to artificial l;ght, for in-stance worn in art;f;c;al light or, qu;te generally, are used in artificial l;ght.
The examples, wh;ch follow~ serve to illustrate ~he inventionO The compounds described by formula are given in the form of free ac;ds; they are generally pre-pared and isolated ;n the form of their sodium or pot-assium sal~s, and they are used ;n the form of the;r sal~sfor dyeing. Similarly, the start;ng compounds men~;oned ;n the form of ~he free ac;d ;n the follow;ng examples~
;n particular tabled examples~ can be used in the syn-thesis as such or in the form of .he;r sal~s, preferably alkali metal salts, such as sodium or potass;um salts.
In the examples, parts are parts by we;ght and percentages are percentages by we;ght, unless o~herw;se stated. Parts by we;ght relate to par~s by volume as ~he kilogram relates to the liter.
Example 1 a) A neutral solut;on of 35.1 par~s of 3-~-sulfatoethyl-sulfonylan;l;ne ;n 130 parts of water is added with eff;-c;ent st;rr;ng to a m;x~ure of 24 parts of cyan~r;c chlor ;de and 130 par~s of ice-waterr The react;on m;xture ;s adjusted to pH 4 - 4.5 and held at this pH during effi c;ent st;rr;ng for five to six hours. This batch is then added with stirring ~o a neutral solut;on of 19~8 parts of 1,3-diam;nobenzene-4-sulfon;c ac;d ;n 2no parts of ;ce-wa~er~ and the result;ng m;xture ;s st;rred at pH 5 - 6 ; for 10 hoursO
b) The solut;on of the secondary condensat;on product pre-pared under a) is cooled do~n to 0C - 5C and adjusted to pH 1 - 2 w;th hydrochlor;c ac;d, and 13D5 parts by volume of an aqueous 40X strength sodium nitr;te solution are added w;th st;rr;ng. 2701 parts of 1-am;no-8 naphthol-3,6-~ lf~ni~ acid are then added portionswise to this ~ n;l~ salt solution, and stirring is continued at a pH between 1.5 and 2 for 10 to 15 hours until the coup-25 ling react;on has ended~
c) An aqueous suspens;on of the conventionally prepared d;azon;um salt of 15.6 par~s of an; l;ne~4-sulfonic ac;d is added to the solution of the monoazo compound prepared ,'~
~ under b), and th;s coupl;ng ba~ch ;s adjus~ed ~o pH 6 - 7 63~
and stirred for about 1 to 2 hours untiL the coupling has ended.
The synthesis solution ;s clarified in a customary manner (addition of kieselguhr, followed by filtration) 5 and evaporated to dryness or spray-dried. This gives 1$0 parts of a black powder which, ;n addition to electrolyte salts~ such as sod;um chLoride, contains about 50% of an alkali metal saltO such as the sodium salt, of the com-pound of the formula Cl N ~12N OI~
n ~ ~I J ~N~ - N~ = N ~ N = ~_ ~
~3~ ~ `S03H S0311 2 C~I2-CH2-OS03~ ~103S
Th;s disazo compound of the invention has very good fiber-reactive dyestuff properties and, when applied and fixed by the methods customary in industry for fiber-reactive dyestuffs, gives on the materials mentioned in the descrip-~ive section, such as, in particular, cellulose fiber materials, strong navy to black dyeings and prints of good to very good in-use and processing fastness pro-perties, of ~hich the following are particularly note~
worthy: light fastness properties on dry or moist fiber material, wash fastness properties (at 60 and 95C)~ fast~
ness to soda boiling, milling, seawater~ rubbing, gas fume fad;n~, hot pressing, water (heavy duty~ and acid cross-dy'e;ng and persp;ration. The dyeings and prints are largely shade-stable to copper ion donors and chlorinated wateru Rfter the clar;fy;ng f;ltration~ the synthesis solution of the novel disazo compound obtained in this example can also be partially evaporated to g;ve a very concentrated solution, since the novel compound is readily soluble in water. This solution can advantageously be adm;xed with customary buffer substances for stabiliz;ng a pH between 3 and 7, and also dispersants and customary suitable, water-misc;ble solvents, such as sulfolane, dimethyl sulfoxide or ethylene glycol dimethyl ether.
The concentrated solutions thus obtained can advantage-ously be used instead of the powders for making up dyeing solutions and pr;n~ pastes ;n dyeing and print;ng. They g;ve the abovement;oned navy to black dyeings and prints ;n the same qual;ty.
Example 2 a) 16.5 parts of cyanuric fluor;de are added w;th effic;ent stirring in the course of 10 minutes to a neutral solu-~ion of 31 parts of 4-~-sulfa~oethylsulfonylan;line in 120 parts of ;ce-water. The batch is stirred at pH 2 - 3.5 for 30 m;nutes, and i5 then admixed with a neutral solu-t;on of 1~.8 parts of 1,3-diaminobenzene-4-sulfon;c ac,d ;n 200 parts of ice water; the batch is then stirred at pH 4~5 - 6 for some hours.
b) The solut;on of this secondary condensation product is then cooled down to 0 to 5C, adjusted to pl~ 1 - 1.5 w;th dilute sulfuric acid and d;azctized by adding 13.5 parts by volume of an aqueous 40% strength sodium nitrite solu~;on~ This diazotization batch is s~irred for 3 hours, and excess nitri~e is destroyed in a cus~omary manner by -add;ng am;dosulfon;c ac;d. The d;a20n;um salt suspens;on thus prepared ;s then admixed w;th 2807 parts of 1-am;no-8-naphthol-4,6-d;sulfon;c ac;d, and this coupling batch ;s st;rred at pH 1 - 2 for 10 hours~
5 c) The solut;on of ~he monoa~o compound prepared under b) in th;s example is adm;xed w;th an aqueous solution of a convent;onally prepared d;azon;um salt of 25.3 parts of anil;ne-2,5-d;sulfon;c ac;d; the coupl;ng react;on ;s com-pleted at pH 6 - 8 ;n the course of about 1 tO 2 hours, 10 and the result;ng solution of the disazo compound of the invention is then adjusted to pH 5. It is convention-al(y clarified and evaporated to dryness or spray-dried.
The disazo compound of ~he invent;on can also be salted out from the synthes;s solut;on w;th potassium chloride, 15 and ;solated.
This gives a blu;sh black electrolyte-contain;ng powder of an alkali metal salt~ such as the sodium or pot-ass;um sal~, of the compound of the formula Cl N ~ N ~12N OEI lSO3 NII ~ `N ~ -NH ~ - N = N ~ ~ \~ N = N -l2 ~ ~ So3~ J ~ So~
CH2 CH2-OS03H ~03S ~03~I
O
Th;s disa~o compound of ~he ;nven~;on has very good fiber-reactive dyestuff proper~ies and, when applied ~o the mater;als mentioned in the descr;p~;ve section, such as, in part;cular, cellulose f;ber mater;als~ by the applica ~;on and f;xing methods customary in ;ndus~ry, ;n par~i-cular for f;ber~react;ve dyestuffs, g;ves s~ron~ redd;sh 3~3 navy to black dyeings and prints having excellent we~
fastness properties, such as, for example, a very good wash Fastness at 6ûC and 95C, a very good acid ~ross-dyeing fastness, very good perspiration fastness 5 propert;es and a very good fastness to gas fume fading~
~xamples 3 to 200 ~ he tabled examples which follo~l describe o~her novel disazo compounds by means of their components (the phenylenediamino compound of the general formuLa ~6), 10 cyanur;c chloride, referred to as (A)~ or cyanuric fluor-ide~ referred to as tB), and the am;no compound of the generaL formula (53 as components of the first diazo com-ponent of ~he general formula (4) and the amino compound D-NH2, which corresponds to the general formula (3), as 15 2nd dia7o component, and 1-amino-8-naphthol-3,~- and -4,6-disulfonic acid as a bivalent coupling component cf ~he monoazo compound of the above formula (2), characterized in the tabled example by the pos;tion of the one sulfo group in 3- or 4-posit;on). They can be prepared from 2D these components ;n the manner of the invention, for example analogously to the above Working Examples.
They have very good fiber-reactive dyes~uff properties and, when applied to the materials mentioned in the de-script;ve section~ such as, in par~icular~ cellulose fiber 25 mater;als, by the appl;cat;on methods customary in indus-try in dye;~g and pr;nting~ preferably by the appl;cation and f;x;ng methods for fiber-reactive dyestuffsO give strong dyeings and prints having good fastness properties and ~he hue g;ven in the part;cular tabled example~
FX- Phenylene Cyanuric Amino Posi~ion Amino compound /3) ~e is navy ample diamine (6) halide com~ound (5) of the on~ of the general sulfo group formula D-NH2 3 1,3-diamino- (A) 4-6-sulfatoethyl- 3 2,4-disulfoaniline (greenish) ben~ene-4- sulfonylaniline - sulfonic acid 4 dirto(A) ditto 3 2,5-disulfoaniline tneutral) ditto(A) ditto 3 2-sulfoaniline tneutral)
Examples of amino compounds of the general for-~ula (5) are 3-(~-sulfatoethylsulfonyl)-aniline, 3-vinyl-sulfonylaniline, 2-methoxy-5-(~-sulfatoethylsulfonyl)~
aniline, 2-methoxy-5-vinylsulfonylaniline, 2,5-dimethoxy-10 4 (~-sulfatoethylsulfonyl)-aniline and ;ts vinylsulfonyl derivative, 2-me~hoxy-4-(~-sulfatoethylsulfonyl)-aniline and its vinylsulfonyl derivative, 4-methoxy-5-(~-sulfato-ethylsulfonyl)-aniline and its vinylsulfonyl derivative, 2,4-dimethoxy-5-~-sulfatoethylsulfonylaniline and its 1~ vinylsulfonyl derivative, 2-methoxy-5-methyl-4-(~-sulfato-ethylsulfonyl)-anil;ne and ;ts v;nylsulfonyl derivative, 2-methoxy-5-chloro-4-(~-sulfatoethylsulfonyl)-aniline and its vinylsulfonyl derivative, but preferably 4-(~-sulfato-ethylsulfonyl)-aniline and 4-vinylsulfonylaniline.
Examples of phenylenediamino compounds of the general formula ~6) are 1,4-diaminobenzene-2,5-disulfonic acid, 1,4~diaminobenzene-2,6-disulfonic acid, 2,5-diamino~
toluene-4-sulfonic acid, 2~4-diaminotoluene-5 sulfonic acid, 2,5~diaminoanisole-4-sulfon;c acid and 2,4 d;amino-anisole-5~sulfon;c acid~ but preferably 1~3-d;aminobenzene-4-sulfonic acid and 1,4-diaminobenzene-5-sulfonic acid~
Those compounds of the invention are preferred in which ~he group of the formula ~S02-X is bonded to the benzene nucleus in meta-position, ;n part;cular in para-position, relat;ve to the am;no group. ~hose compounds of the invention are also preferred in wh;ch the moiety X represents the ~-sulfatoethyl group.
Moreover, ;n disazo compounds of the general for-mula (1), the moiety R1 is pre~erably a hydrogen atomor a methyl group or a methoxy group or a chlorine atom, R2 is preferably a hydrogen atom, a methyl group or a methoxy group and R is preferably a hydrogen a~om or a sul-fo group.
1~ Furthermore, in compounds of the ;nvention, the moiety D is preferably a phenyl rad;cal which ;s substi-tuted by one, two or three substituents which are sel-ected from the group cons;sting of 2 alkoxy groups of 1 to 4 carbon atoms, 2 alkyl groups of 1 to 4 carbon atoms, 2 chlorine atoms~ 1 bromine atom, 1 fluorine atom~ 1 tri~
chloromethyl group, 1 trifluoromethyl group~ 1 alkanoyl a~;no group having 1 to ~ carbon atoms in the alkyl rad;-cal, 1 n;tro group, 1 carboxy group and 2 sulfo groups.
D ;s part;cularly preferably the phenyl rad;cal wh;ch is substituted by 1, 2 or 3 substituents selected from the group consist;ng of 2 alkoxy groups, such as, in part;cu-lar, me~hoxy groups, 2 chlorine atoms, 2 sulfo groups, 1 carboxyl group, 1 nitro group, 1 alkyl group of 1 ~o 4 carbon atoms, such as, in particular, a Methyl group, and 1 acetylam;no group. D ;s ir, par~;cular a phenyl rad;ca~
wh;ch is subst;tuted by one or two sulfo 0roups.
D is also preferably a naphthyl radical whish ;s subst~tuted by 1, 2 or 3 sulfo groups~
No~eworthy ind;vidual compounds are espesially 96~
the novel disazo cornpounds descr;bed in Examples 1 to 9, 13, 17, 19 and 20~
Compounds of the ~eneral -formula (1) prepared according to the invention can be separated and isolated 5 from the synthesis solutions by generally known methods, for example by precipitating them from the reaction medium by means of electrolytes~ such as, for example, sodium chloride or potassium chloride, or by evapora~ing, for example spray~drying~ the reaction solution, to which a 10 buffer substance, such as, for example, a rnixture of monosodium and disodium phosphates can be added. If appro-priate, ~hese synthesis solutions, if necessary after a buffer substance has been added and/or they have been con-centrated, can also be used in dyeing directly as a liquid 15 formulat;on.
D;sazo compounds of the ;nvent;on have valuable dyestuff properties which~ by virtue of the v;nylsulfonyl or ~-sulfatoethylsulfonyl group and the halogenotriazinyl radical, have fiber-reactive properties~ The new com-20 pounds are preferably used for dyeing ~in the generalsense as ;nclud;ng print;ng) llydroxy- and/or carboxalnide~
containing mater;als, for example in the fc,rm of ~heet-l;ke struc~ures, such as paper and leather or sheeting, such as, for example, made of polyamide, or in the mass, 25 such as, for example, polyamide and polyurethane, but in particular these ma~erials in fiber form~ ~he presen~
invention accordingly also relates to the use of co~pounds o~ the general formula (1) for dyeing ~in the above sense~
these materials or rather to methods for dyeing such materials in conventional methods ;n which a compound of the general formula t1) ;s used as a coloran~ In these methods the materials are preferably ;n the form of f;ber mater;als, ;n particular in the form of textile fibers, 5 such as yarns, packages, or woven or knitted fabr;cs.
~ Iydroxy ~containin~ materials are natural, regen-erated or synthetic hydroxy -containing materials, such as, for example, cellulose fiber mater;als or regenera~ed cellulos;c mater;als or polyvinyl alcohols. Cellulose f;ber materials are preferably cottonr but also other vege~able fibers, such as linen, hemp~ jute or ram;e fibers; examples of regenerated cellulose f;bers are v;s-c~se staple and filament v;scose~
Examples of carboxam;de-con~a;n;ng mater;als are synthet;c nylons, such as nylon ~,6, nylon 6, nylon 11 or nylon ~, and polyurethanes, ;n part;cular ;n the form of f;bers, or natural polyam;des, for example wool or other an;mal ha;rs, s;lk or leather.
D;saz.o compounds of the ;nvent;on can be applied and f;xed to sa;d substrates, ;n part;cular to sa;d f;ber mater;als, by the appl;cat;on techniques known for water-soluble dyestuffs, ;n particular for fiber-react;ve dye-stuffs~ .
~or ;nstance, on cellulose f;bers they g;ve ;n the exhaus~ me~hod in ~he presence of various ac;d accep-tors and, if desired~ neutral salts, such as sodium chlor~
idè or sodium sulfate, very good color yields and excel-lent color bu;ld~upn Dye;ng ;s carried out at ~empera-tures between ~ and 105C~ preferably bet~Jeen 60 and : ' a~;3~
100C, ;f appropr;ate at temperatures up to 120C under pressure, ;f appropr;ate in the presence of customary dye;ng aux;Liaries~ in an aqueous bath, by ;ntroduc;ng the fiber material into a warm bath and gradually raising 5 this to the desired dyeing temperature and complet;ng the dye;ng process at this temperature~ If desired, neutral salts which accelerate the exhaus~ion of the dyestuff can also be added to the bath only after the dyeing tempera-ture proper has been reached~
The padding method also gives excellent color y;elds on cellulosic fibers, on wh;ch the dyes can be fixed ;n a customary manner by leaving the dyeing to stand at room temperature or elevated temperature, for example up to 60C, by steam;n3 or by means of dry heat~
S~rong pr;nts hav;ng well-delineated contours and ~ a clear white ground are also obtained in customary print-: ing methods for cellulosic fibers~ which can be carried out in one step - for example by printing with a print paste containing sodium bicarbonate or a d;fferent ac;d-b;nd;ng agent and then steaming at 100 bo 103C - or ~h'O
steps - for example by printing wi~h a neutral or weakly acid print paste and then fix;ng either by passing the printed goods through a hot electrolyte-conta;ning alkal-ine bath or by overpadding w;th an alkal;ne electrolyte-conta;ning padd;ng liquor and then leaving the material : overpadded to stand or steaming it or ~reating ;t with dry heat. ~ The ou~come of the prin~s is hardly depen-:; dent on varying fix;ng conditions, if at all~ The .. degrees of fixation obtained with the compounds o-f the .. ..
;nvention not only in dye;ng but also ;n pr;nt;ng are very h;gh~
In add;tion to customary steam at 100to 103C, ;t is also poss;ble to use superheated steam or saturated 5 steam at temperatures of up to 160Ca In dry heat f;xing by customary thermof;x;ng methods, hot air at 120 to 200C
is used.
Examples of the agents which bind acid and effect the fixat;on of compounds of the invention on celLulosic 10 fibers are water-soluble basic salts of alkali metals and also alkaline earth metals of inorganic or organic acids or compounds which liberate alkali when heated. The alkali metal hydroxides and aLkali metal salts of ~leak to medium inorganic or organic acids are particularly 15 noteworthy, the sodium and potassium compounds being intended ;n particular among the alkal; metal compounds.
Examples o, such acid-b;nding agents are sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, sodium formate, sodium dihydrogen-20 phosphate, d;sod;um hydroQenphosphate, sod;um tr;chloro-acetate, sod;um s;l;cate and tr;sod;um phosphate.
The treatment of compounds of the invention with acid bind;ng agencs, if appropriate under heat~ bonds ~he compounds of the invent;on chem;cally to the cellulose 25 fiber. The cellulose dyeings, ;n particular, have excel-len~ manufacturing and end~use fastness propercies, such as~ in parti~ular, wet fastness propert;es, after the cus tomary aftertreatmen~ whereby unf;xed dyestuff portions are removed by rinsing~
~ 15 -As regards the coloristic properties of compounds according to the invention, ;t is particularly note~orthy that they are distinguished by good stability in print pastes and padding liquors, even in the presence of alka-S lis, by very good a~finity from a long liquor, by goodcoLor build-up in customary dyeinQ and printing methods, by an even depth of shade in the dyeing of cotton and regenerated cellulose f;bers, by the levelness of the dye-;ngs and prints prepared with them and also by the fact 1D that long l;quor dyeings are level i~ various amounts of electrolyte have been added. Unfixed dyestuff portions can be readily washed out.
Polyurethane fibers and polyamide fibers are cus-tomarily dyed from an ac;d med;um. ~or example, acet;c ac;d and/or ammon;um sulfate or acet;c acid and ammonium acetate or sodium acetate can be added to the dyeba~h to obtain the desired pH. To obtain an acceptably level dyeing, it is advisable to add customary level;ng auxili-aries~ such as, for e~ample, those based on a reaction product of cyanur;c chlor;de w;th three t;mes the molar amount of an am;nobenzenesulfonic ac;d and/or an am;no-naphthalenesulfonic acid or ~hose based on a react;on pro-duct of, for example, stearylamine with ethylene oxide~
The material to be dyed is generally ;ntroduced at a tem-~5 perature of about 40C into the initially slightly alka-line bath, and ag;tated there;n for some t;me, the dye bath ;s brought to a weakly ac;d~ preferably weakly ace-tic ac;d pH, and the actual dyeing is carr;ed out at a temperature between 30 and 105C~ pre~erably between ~0 and 100Cn Disazo compounds of the ;nvention are distin-guished in the dyeing and printing of fiber materials by a high degree of fixation, ~hich fact is economically, 5 energyw;se and ecologically of great benefit in ;ndustry, since a h;gh ut;l;zation of the dyestuff offered by a higher f ~ tion mgans an energy saving and easier washiny-out of the~reduc~d)unfixed dyestuff portion~and additionally the effluent is less polluted.
Dyeings and prints prepared ~ith disazo compounds of the formula ~1~ are d;stinguished by bright shades.
The dyeings and prints on cellulosic fiber mater;als, in part;cular, have, as already mentioned, a great tinctorial strength and, furthermore, very good light fastness pro-15 perties(not only in the dry but also in the moist stat~, and very good fast~esses to was~ing with both peroxide-free and peroxide containin~ detergents, to milling~ toand water A sea~ater,and acid fastness properties, and also very good crossdyeing fastness properties, such as, in 20 particular, very good acid crossdyeing fastness properties, and very good persp;ration fastness properties, and also good pleat;ng, hs~ pressing~ rubb;ng and gas fume fading fastness properties~ They are also highly resistant ~o chlorina~ed ~ater and copper ion donors; they are there-25 fore compatible~ for example~ ~ith copper complex dye-stuffs. Nor does ~he use of compounds of the invention in dyeing cellulosic fiber ma~erials harden the hand of the dyed material.
Neither print pastes, nor padd;n~ l;quors~ nor f C~ 17 -dye;n~ liquors nor unfixed prin~s or pad-dyeings wi~h com~
pounds of the invention are sensi~ive to gases which are acid or contain sulfur dioxide~
Dyeings prepared with compounds of the invention S have navy to black shades; they generally do not exh;bit in art;fic;al l;ght the unfavorable, undesirable reddish tinge which leads to the 'red even;ng shade~ since they generally have a sl;ghtLy more green;sh t;nge. Fr,r th;s reason the compounds of the invent;on generally have a 10 llneutral~evening shade, so that ;t is not necessary to blend the disazo compounds of che ;nvent;on w;th a su;t-able shading dyestuff; for dyestuffs which exper;ence a marked sh;ft in hue under art;ficial light have the disad-vantage that it not only restr;cts their general suit-abil;ty for prepar;ng dye;ngs but also complicates theiruse in the preparation of dyeings when shad;ng dyestuffs have to be added to obta;n dyeings which are reasonably satisfac~ory when exposed to artificial l;ght, for in-stance worn in art;f;c;al light or, qu;te generally, are used in artificial l;ght.
The examples, wh;ch follow~ serve to illustrate ~he inventionO The compounds described by formula are given in the form of free ac;ds; they are generally pre-pared and isolated ;n the form of their sodium or pot-assium sal~s, and they are used ;n the form of the;r sal~sfor dyeing. Similarly, the start;ng compounds men~;oned ;n the form of ~he free ac;d ;n the follow;ng examples~
;n particular tabled examples~ can be used in the syn-thesis as such or in the form of .he;r sal~s, preferably alkali metal salts, such as sodium or potass;um salts.
In the examples, parts are parts by we;ght and percentages are percentages by we;ght, unless o~herw;se stated. Parts by we;ght relate to par~s by volume as ~he kilogram relates to the liter.
Example 1 a) A neutral solut;on of 35.1 par~s of 3-~-sulfatoethyl-sulfonylan;l;ne ;n 130 parts of water is added with eff;-c;ent st;rr;ng to a m;x~ure of 24 parts of cyan~r;c chlor ;de and 130 par~s of ice-waterr The react;on m;xture ;s adjusted to pH 4 - 4.5 and held at this pH during effi c;ent st;rr;ng for five to six hours. This batch is then added with stirring ~o a neutral solut;on of 19~8 parts of 1,3-diam;nobenzene-4-sulfon;c ac;d ;n 2no parts of ;ce-wa~er~ and the result;ng m;xture ;s st;rred at pH 5 - 6 ; for 10 hoursO
b) The solut;on of the secondary condensat;on product pre-pared under a) is cooled do~n to 0C - 5C and adjusted to pH 1 - 2 w;th hydrochlor;c ac;d, and 13D5 parts by volume of an aqueous 40X strength sodium nitr;te solution are added w;th st;rr;ng. 2701 parts of 1-am;no-8 naphthol-3,6-~ lf~ni~ acid are then added portionswise to this ~ n;l~ salt solution, and stirring is continued at a pH between 1.5 and 2 for 10 to 15 hours until the coup-25 ling react;on has ended~
c) An aqueous suspens;on of the conventionally prepared d;azon;um salt of 15.6 par~s of an; l;ne~4-sulfonic ac;d is added to the solution of the monoazo compound prepared ,'~
~ under b), and th;s coupl;ng ba~ch ;s adjus~ed ~o pH 6 - 7 63~
and stirred for about 1 to 2 hours untiL the coupling has ended.
The synthesis solution ;s clarified in a customary manner (addition of kieselguhr, followed by filtration) 5 and evaporated to dryness or spray-dried. This gives 1$0 parts of a black powder which, ;n addition to electrolyte salts~ such as sod;um chLoride, contains about 50% of an alkali metal saltO such as the sodium salt, of the com-pound of the formula Cl N ~12N OI~
n ~ ~I J ~N~ - N~ = N ~ N = ~_ ~
~3~ ~ `S03H S0311 2 C~I2-CH2-OS03~ ~103S
Th;s disazo compound of the invention has very good fiber-reactive dyestuff properties and, when applied and fixed by the methods customary in industry for fiber-reactive dyestuffs, gives on the materials mentioned in the descrip-~ive section, such as, in particular, cellulose fiber materials, strong navy to black dyeings and prints of good to very good in-use and processing fastness pro-perties, of ~hich the following are particularly note~
worthy: light fastness properties on dry or moist fiber material, wash fastness properties (at 60 and 95C)~ fast~
ness to soda boiling, milling, seawater~ rubbing, gas fume fad;n~, hot pressing, water (heavy duty~ and acid cross-dy'e;ng and persp;ration. The dyeings and prints are largely shade-stable to copper ion donors and chlorinated wateru Rfter the clar;fy;ng f;ltration~ the synthesis solution of the novel disazo compound obtained in this example can also be partially evaporated to g;ve a very concentrated solution, since the novel compound is readily soluble in water. This solution can advantageously be adm;xed with customary buffer substances for stabiliz;ng a pH between 3 and 7, and also dispersants and customary suitable, water-misc;ble solvents, such as sulfolane, dimethyl sulfoxide or ethylene glycol dimethyl ether.
The concentrated solutions thus obtained can advantage-ously be used instead of the powders for making up dyeing solutions and pr;n~ pastes ;n dyeing and print;ng. They g;ve the abovement;oned navy to black dyeings and prints ;n the same qual;ty.
Example 2 a) 16.5 parts of cyanuric fluor;de are added w;th effic;ent stirring in the course of 10 minutes to a neutral solu-~ion of 31 parts of 4-~-sulfa~oethylsulfonylan;line in 120 parts of ;ce-water. The batch is stirred at pH 2 - 3.5 for 30 m;nutes, and i5 then admixed with a neutral solu-t;on of 1~.8 parts of 1,3-diaminobenzene-4-sulfon;c ac,d ;n 200 parts of ice water; the batch is then stirred at pH 4~5 - 6 for some hours.
b) The solut;on of this secondary condensation product is then cooled down to 0 to 5C, adjusted to pl~ 1 - 1.5 w;th dilute sulfuric acid and d;azctized by adding 13.5 parts by volume of an aqueous 40% strength sodium nitrite solu~;on~ This diazotization batch is s~irred for 3 hours, and excess nitri~e is destroyed in a cus~omary manner by -add;ng am;dosulfon;c ac;d. The d;a20n;um salt suspens;on thus prepared ;s then admixed w;th 2807 parts of 1-am;no-8-naphthol-4,6-d;sulfon;c ac;d, and this coupling batch ;s st;rred at pH 1 - 2 for 10 hours~
5 c) The solut;on of ~he monoa~o compound prepared under b) in th;s example is adm;xed w;th an aqueous solution of a convent;onally prepared d;azon;um salt of 25.3 parts of anil;ne-2,5-d;sulfon;c ac;d; the coupl;ng react;on ;s com-pleted at pH 6 - 8 ;n the course of about 1 tO 2 hours, 10 and the result;ng solution of the disazo compound of the invention is then adjusted to pH 5. It is convention-al(y clarified and evaporated to dryness or spray-dried.
The disazo compound of ~he invent;on can also be salted out from the synthes;s solut;on w;th potassium chloride, 15 and ;solated.
This gives a blu;sh black electrolyte-contain;ng powder of an alkali metal salt~ such as the sodium or pot-ass;um sal~, of the compound of the formula Cl N ~ N ~12N OEI lSO3 NII ~ `N ~ -NH ~ - N = N ~ ~ \~ N = N -l2 ~ ~ So3~ J ~ So~
CH2 CH2-OS03H ~03S ~03~I
O
Th;s disa~o compound of ~he ;nven~;on has very good fiber-reactive dyestuff proper~ies and, when applied ~o the mater;als mentioned in the descr;p~;ve section, such as, in part;cular, cellulose f;ber mater;als~ by the applica ~;on and f;xing methods customary in ;ndus~ry, ;n par~i-cular for f;ber~react;ve dyestuffs, g;ves s~ron~ redd;sh 3~3 navy to black dyeings and prints having excellent we~
fastness properties, such as, for example, a very good wash Fastness at 6ûC and 95C, a very good acid ~ross-dyeing fastness, very good perspiration fastness 5 propert;es and a very good fastness to gas fume fading~
~xamples 3 to 200 ~ he tabled examples which follo~l describe o~her novel disazo compounds by means of their components (the phenylenediamino compound of the general formuLa ~6), 10 cyanur;c chloride, referred to as (A)~ or cyanuric fluor-ide~ referred to as tB), and the am;no compound of the generaL formula (53 as components of the first diazo com-ponent of ~he general formula (4) and the amino compound D-NH2, which corresponds to the general formula (3), as 15 2nd dia7o component, and 1-amino-8-naphthol-3,~- and -4,6-disulfonic acid as a bivalent coupling component cf ~he monoazo compound of the above formula (2), characterized in the tabled example by the pos;tion of the one sulfo group in 3- or 4-posit;on). They can be prepared from 2D these components ;n the manner of the invention, for example analogously to the above Working Examples.
They have very good fiber-reactive dyes~uff properties and, when applied to the materials mentioned in the de-script;ve section~ such as, in par~icular~ cellulose fiber 25 mater;als, by the appl;cat;on methods customary in indus-try in dye;~g and pr;nting~ preferably by the appl;cation and f;x;ng methods for fiber-reactive dyestuffsO give strong dyeings and prints having good fastness properties and ~he hue g;ven in the part;cular tabled example~
FX- Phenylene Cyanuric Amino Posi~ion Amino compound /3) ~e is navy ample diamine (6) halide com~ound (5) of the on~ of the general sulfo group formula D-NH2 3 1,3-diamino- (A) 4-6-sulfatoethyl- 3 2,4-disulfoaniline (greenish) ben~ene-4- sulfonylaniline - sulfonic acid 4 dirto(A) ditto 3 2,5-disulfoaniline tneutral) ditto(A) ditto 3 2-sulfoaniline tneutral)
6 ditto(A3 ditto 3 3-sulfoaniline tneutral)
7 ditto(A) ditto 3 4-çhloro-2-sulfoaniline (neutral)
8 ditto(A) ditto 3 4-methoxy-2-sulfoaniline ~greenish)
9 ditto. ~A) ditto 3 2-chloro-4-sulfoaniline ~greenish) ditto~A) ditto 3 2,5-dimethoxy-4-sulfoaniline ~greenish~
11 ditto~A) ditto 3 3-carboxyaniline ~neutral) 12 ditto~A) ditto 3 4-acetylamino-2-sulfoaniline ~greenish) 13 ditto(A) ditto 3 1,5-disulTo-2-naphthylamine (greenish) 14 ditto~A) ditto 3 3,6-disulfo-2-naphthylamine ~greenish) -15 dit~o~A) ditto 3 4,8-disulfo-2-naphthylamine ~greenish) 16 ditto~A) ditto 3 3,6,8-trisulfo-2-naphthylamine ~greenish) 17 ditto~A~ ditto 3 1-sulfo-2-naphthylamine (greenish) 18 ditto(A) ditto 3 6-sulfo-2-naphthylamine ~greenish) - 19 ditto~A) ditto 3 -- 4-sulfo-1-naphthylamine (greenish) ditto~A) 4-vinylsulfonyl~ 3 4-sulfoaniline ~greenish) aniline 21 ditto(A) ditto 3 2,4-disulfoaniline ~neutral) Ex- Phenylene- Cyanuric Amino Pos;tion Am;no compound ~3) Hue is navy ample diamine t6) haL;de csmpound ~5~ of the one of the general sulfo group formula D-NH2 22 1~3-diamino- (A) 4-vinylsulfonyl- 3 2,5-disulfoaniline (greenish) benzene-4- aniline sulfonic acid 23 ditto (A) ditto 3 1,5-disulfo-2-naphthylamine (greenish) 24 ditto (A) ditio 3 3,6-disulfo-2-naphthylamine ~greenish) ditto (A) ditto 3 3,6,8-trisulfo-2-naphthylamine (greenish~
26 ditto (A3 ditto 3 1,5,7-trisulfo-2-naphthylamine (greenish) 27 ditto (A) ditto 3 4,6,8-trisulfo-2-naphthylamine (greenish) 28 ditto (A) ditto 4 4-sulfoaniline (reddish) 29 ditto (A) ditto 4 2,4-disulfoaniline (neutral) ditto (A) ditto 4 2,5-disulfoaniline (reddish) ~e 31 ditto (A) ditto 4 1 "-disulfo-2-naphthylamine (neutral) 32 ditto (A) ditto 4 3,6-disulfo-2-naphthylamine (neutral) 33 ditto (A) ditto 4 4,8-disulfo~-naphthylamine (neutral) 34 ditto (A) ditto 4 6,8-disulfo-2-naphthylamine (neutral) ditto (A) ditto 4 - 1,5,7-trisulfo-2-napthylamine (neutral) 36 ditto (A) ditto 4 3,6,8-trisulfo-2-naphthylamine (neutral) 37 ditto (A) ditto 4 4,6,8-trisulfo-2-naphthylamine (neutral~
38 ditto (A) 4-~j-sulfatoethyl- 4 - 4-sulfoaniline (reddish) - sulfonylaniline 39 ditto (A) ditto 4 2-carboxyaniline (reddish) ditto (A) ditto 4 2,4-disulfoaniline (neutral) 41 ditto ~A) ditto 4 2,5-disulfoaniline (reddish) EX- Phenylene- ~yanuric Amino Position Amino ~ompound ~3) Hue is navy - ample d;am;ne (6) halide compound (5) of the one of the general sulfo group formula D-NH2 42 1~3-diamino- (A) 4-B-sulfatoethyl- 4 2-sulfoaniline (reddish) benzene-4- sulfonylan;line - sulfonic acid 43 ditto (A) ditto 4 3-sulfoaniline (reddish) ~4 ditto (A~ ditto 4 4-carboxyaniline (neutral) ditto (A) ditto 4 4-chloro-Z-sulfoaniline (neutral) -46 ditto (A) ditto 4 4-acetylamino-2-sulfoaniline tneutral) 47 ditto (A) ditto 4 1-sulfo-2-naphthylamine (neutral) 48 ditto (A) ditto 4 6-sulfo-2-naphthylamine (neutral) 49 ditto (A) ditto 4 1,5-disulfo-2-naphthylamine (neutral) ditto (A) dittG 4 4,8-disulfo-2-naphthylamine (neutral) C~
51 ditto (A) ditto 4 6S8-disulfo-2-naphthylamine (neutral) 52 ditto (A~ ditto 4 1,5,7-trisulfo-2-naphthylamine (neutral) 53 ditto (A) ditto - 4 3,6,8-trisulfo-2-naphthylamine (neutral) 54 ditto (A) ditto 4 4-sulfo-1-naphthylamine (greenish) 1,4-diamino- (A) ditto 3 4-sulfoaniline (greenish) benzene 2-sulfonic acid 56 ditto (A) ditto 3 2,5-disulfoaniline (greenish) 57 di-t~o (A) ditto 3 4-sulfo-1-naphthylamine (greenish) 58 -ditto (A) ditto 3 1,5-disulfo-2-naphthylamine (greenish) 59 ditto (A) ditto 3 1,5,7-trisulfo-2-naphthylamine (greenish) ditto (A) ditto 3 2-sulfoaniline (greenish) Ex~ Phenylen~- ~yanuric Amino Position Amino compound ~3) Hue is navy amp~e diamine (6) halide compound (5) of ~he one of the general sulfo group formula D-NH2 61 1~3-diamino- (A) 4-~-sulfabo~ _ 3 4-sulfoaniline ~neutral) benzene-4,6- ethylsulfony~ani disulfonic acid line 6Z ditto (A) ditto 3 2,4-disulfoaniline (greenish~
63 ditto (A) ditto 3 Z-carboxyaniline (neutral) 64 ditto tA) ditto 3 4-carboxyaniline (greenish) ditto (A) ditto 3 2-chloroaniline (neutral) 66 ditto (A) ditto 3 4-chloro-2-sulfoaniline (neutral) 67 clitto (A) ditto 3 1-sulfo-2-naphthylamine (greenish) 68 ditto (A) ditto 3 1,5-disulfo-2-naphthylamine (greenish) 69 ditto (A) ditto 3 6-sulfo-2-naphthylamine (greenish) p~
ditto (A) ditto 3 Z,5-dichloro-4-sulfoaniline (greenish) 71 ditto (A) ditto 3 2,5-dimethoxy-4-sulfoaniline (sreenish) 72 1~4-diamino- (A) ditto 3 4-sulfoaniline (greenish) benzene-2,5-disulfonic acid 73 ditto (A) ditto 3 2-carboxyaniline (greenish) 74 ditto (A) ditto 3 4-carboxyaniline (greenish) ditto (A) ditto 3 2-chloroaniline (greenish) 76 ditto (A) ditto 3 2-sulfoaniline (greenish) 77 dit~o (A) ditto 3 4-sulfo-1-naphthylamine (greenish) 78 ditto (A) ditto 3 1-sulfo-2-naphthylamine (greenish) Ex- Phenylene- Cyanuric Amino Position Amino compound (3) Hue is navy ampie diamine (6) ~alide compound (5) of the one of the general sulfo sroup formula D-N~2 79 1,4-diamino- (A) 4-B-sulfato- 3 6-sulfo-2-naphthylamine (greenish) benzene-Z,S- ethylsulfonyl-disulfonic aniline acid ~0 ditto SA) ditto 3 1,5-disulfo-2-naphthylamine (greenish~
81 1,4-diamino- (A) ditto 3 4-sulfoaniline (sreenish) benzene-2,6-disulfonic acid 82 ditto(A) ditto 3 2-sulfoaniline - (greenish) 83 ditto(A) ditto 3 2-carboxyaniline (greenish) 84 ditto(A) ditto 3 2-chloroaniline (greenish) ditto(A) ditto 3 4-acetylamino-3-sulfoaniline (greenish) 86 ditto(A) ditto 3 4-sulfo-1-naphthylamine (greenish) 87 ditto~A) ditto 3 1-sulfo-2-naphthylamine (greenish) 88 ditto(A) ditto 3 6-sulfo-2-na~hthylamine (greenish) 89 ditto. (A) ditto 3 6,8-disulfo-2-naphthylamine (greenish) ditto(A) ditto 3 1,5-disulfo-2-naphthylamine (greenish) 91 1,4-diamino- (A) ditto 4 4-sulfoaniline (greenish) benzene-2-sulfonic acid 92 ditto(A) dit~o 4 2,5-disulfoaniline (greenish) 93 ditto(A) ditto 4 2-sulfoaniline (greenish) 94 ditto(A) ditto 4 1,5-disulfo-2-naphthylamine (greenish) Ex- Pheny(ene- Cyanuric Amino Posit;on Amino compound (3) Hue is navy ample diamine (6) halide compound (5) of the one of the general sulfo group formula D-NH2 95 1,4-diamino- (A) 4-~-sulfato- 4 4-sulfo-1-naphthylamine (greenish) benzene-2- ethylsulfonyl-sulfonic acid aniline 96 ditto (A) ditto 4 Z-sulfoaniline (greenish) 97 1,3-diamino- ~A) ditto 4 4-sulfoaniline (reddish) benzene-4,6- -disulfonic acid 98 ditto (A~ ditto 4 4-sulfo-1-naphthylamine (neutral) - 99 ditto (A) ditto 4 1~5-disulfo-2-naphthylamine (neutral) 100 ditto ~A) ditto 3 1-sulfo-2-naphthylamine (neutral) ~
101 ditto (A) ditto 3 2,4-disulfoaniline (reddish) Gg 102 ditto (A) ditto 3 2-chloroaniline (reddish) t~
103 1,4-diamino- (A) ditto 4 4-sulfoaniline (greenish) - benzene-2,5-disulfonic acid 104 ditto (A) ditto 4 3-sulfoaniline (neutral) 105 ditto (A) ditto 4 2-sulfoaniline (neutral) 106 ditto ~A) ditto 4 1-sulfo-2-naphthylamine (greenish) 107 ditto (A) ditto 4 - 1,5-disulfo-2-naphthylamine (greenish) 108 ditto (A) ditto 4 2-chloroaniline (neutral) 109 1,4-diamino- (A) ditto 4 4-sulfoaniline (neutral) benzene-2,6-disulTonic acid Ex- Phenylene- Cyanuric Amino Position Am;no compound (3) Hue is n2vy a~ple diamine (6) halide compound (5) of the one of the general sulfo group formula D-NH2 110 1,4-diamino- (A~ 4-~-sulfato- 4 2-sulfoaniline (neutral) benzene-2,6- ethylsulfonyl-disulfonic aniline acid 111 ditto (A) ditto 4 4-sulfo-1-naphthylamine (greenish) 112 ditto (A~ ditto 4 1,5-disulfo-Z-naphthylamine tgreenish) 113 2,5-diamino- (A~ ditto 3 4-sulfoaniline (greenish) toluene-4 ~
sulfonic acid `O
114 ditto (A) ditto 3 2-sulfoaniline (greenish) 115 ditto (A) ditto 3 1-sulfo-2-naphthylamine (greenish) 116 ditto (A) ditto 3 1,5-disulfo-2-naphthylamine (greenish) ~ç
117 2,4-diamino- (A) ditto 3 4-sulfoaniline (neutral) ~:
~oluene-5- -sulfonic acid 11~ ditto (A) ditto 3 2,5-disulfoaniline (neutral) 119 ditto ~h) ditto 3 1,5-disulfo-2-r,aphthylamine (neutral~
120 ditto (A) ditto 3 3,6-disulfo-2-naphthylamine (r,eutral) 121 Z,5-diamino- (A) ditto 3 4-sulfoaniline (greenish) anisole-4-sulfonic acid 122 d;tto (A) ditto 3 1,5-disulfo-2-naphthylamine (greenish) 123 ditto (A) ditto 3 2,5-disulfoaniline (greenish) 124 ditto (A) ditto 3 2,4-disulfoaniline (greenish) Ex- Phenylene~ ~yanuric Am;no Posit;on Amino compound (3) Hue ;s navy ample diamine (6~ halide compou~d (53 of the one of the general sulfo group formula D-NH2 12~ 2,4-diamino- tA) 4~ sulfato- 3 4-sulfoaniline ~neutral) anisole-5- ethylsulfonyi-sulfonic acid aniline 126 ditto ~A) ditto 3 1,5-disulfo-2-naphtylamine(neutral) 127 ditto (A) ditto 3 1~5,7-trisulfo-2-naphthylamine (greenish) 128 1~3-diamino- (A) 3-~-sulfato- 3 4-sulfoaniline (neutral) benzene-4- ethylsulfonyl-sulfonic acid aniline 129 ditto (A) ditto 3 2-sulfoaniline (neutral) w 130 ditto (A) ditto 3 2,4-disulfoaniline ~neutral) 131 ditto (A) ditto 3 2,5-disulfoaniline (neutral) 132 ditto (A) ditto 3 1,5-disulfo-2-naphthylamine(greenish~
133 ditto (A) ditto 3 4,8-disulfo-2-naphthylamine(greenish) 134 ditto (A) ditto 3 4-sulfo-1-naphthylamine (greenish) 135 ditto (A) 2-methoxy-4-~6-sul- 3 4-sulfoaniline (neutral) fatoethylsulfonyl)~
aniline 136 ditto (A) ditto 3 2,5-disulfoaniline (neutral) 137 ditto (A) ditto 3 4-sulfo~-naphthylamine (greenish) 138 ditto (A) ditto 3 1,5-disulfo-2-naphthylaminegreenish) 13q ditto (A) 2-methoxy-5-~-sul- 3 2-sulfoaniline (neutral) fatoethylsulfonyl~-aniline 140 ditto (A) ditto 3 2,4-disulfoaniline (neutral) 141 ditto (A) ditto 3 4-sulfo-1-llaphthylamine (greenish) Ex- Phenylene- Cyanuric Amino ~osit;on Amino conpound t3) Hue is navy ample diamine ~6) halide compound ~5) of the one of the general sulfo grGup formula D-NH2 142 1,3-diamino- (A) 2-methoxy-5- ~-sul- 3 1,5-disulfo-2-naphthylamine (greenish) benzene-4- fatoethylsulfonyL)-sulfonic acid aniline 143 ditto (A) 2-methoxy-5-methyl- 3 4-sulfoaniline (neutral) 4- ~-sulfatoethyl-sulfonyl)-aniline 144 ditto (A) ditto 3 2,5-disulfoaniline (neutral) 145 ditto (A) ditto } 4-sulfo-1-naphthylamine (greenish) 146 ditto (A) ditto 3 1,4-disulfo-2-naphthylamine (sreenish) 147 ditto (A) 2,5-dimethoxy-4- 3 2-sulfoaniline (neutral) ~-sulf~toethylsul- ~
fonyl) aniline CD
14~ ditto (A) ditto 3 4-sulfoaniline (neutral) 149 dit~o (A~ ditto 3 2,5-disulfoaniline (neutral) 2 150 ditto (A3 ditto 3 1,5 disulfo-2-naphthylamine (greenish) 151 ditto (A) ditto 3 - 4-sulfo-1-naphthylamine (greenish) 152 ditto ~A) 2-methoxy-5-chloro- 3 2-sulfoaniline (neutral) 4- ~-sulfatoethyl-sulfonyl)-aniline 153 ditto (A) ditto 3 4-sulfo-1-naphthylamine (sreenish) 154 ditto (A) ditto 3 -- 2,5-disulfoaniline (neut al) 155 ditto (A) ditto 3 1,5-disulfo-2-naphthylamine (greenish) 156 ditto (A) 4-methoxy-5- ~-sul- 3 4-sulfoaniline (neutral) fatoethylsulfonyl)-aniline Ex~ Phenylene Syanuric Amino Position Amino compound (3) Hue ;s navy ample diamine (6~ halide compound (5) of the one of the general sulfo group formula D-NH2 157 1,3-di am ino- (A) 4-methoY~y-S- ~- 3 2-sulfoaniline (neutral) benzene-4- sulfatoethylsul~
sulfonic acid fonyl)-aniline 158 ditto (A) ditto 3 2,5-disulfoaniline (neutral) 159 ditto (A) ditto 3 1,5-disulfo-2-naphthylamine (greenish) 160 ditto (A) 2-methoxy-5- ~- 4 2-sulfoaniline (neutral) sulfatoetnylsul-fonyl)-aniline 161 ditto (A) ditto 4 2,4-disulfoaniline (neutral) 162 ditto (A) ditto 4 1,5-disulfo-2-naphthylamine (neutral) 163 di~to (A) ditto 4 4-sulfo-1-naphthylamine (greenish) 164 ditto (A) 2-methoxy-5-vinyl- 4 2,5-disulfoaniline (reddish) ~
sulfonylaniline ~`
165 ditto (A) ditto 4 1,5-disulfo-2-naphthylamine (neutral) 166 ditto (B) 4-~3-sulfatoethyl- 3 4-sulfoaniline (neutral) sulfonylaniline 167 ditto . (B) ditto 3 1j5-disulfo-2-naphthylamine (greenish) 168 ditto (B) 4-vinylsuifonyl- 3 2,5-disulfoaniline (neutral) aniline 169 ditto (B) ditto 4 ditto (reddish) 170 ditto (8) ditto 4 4-sulfoaniline (reddish) 171 ditto (B) ditto 4 1,5-disulfo-2-naphthylamine (neutral) 172 ditto (B, 3-6-sulfatoethyl- 4 2-sulfoaniline (reddish) sulfonylaniline Ex- Phenylene- Cyanur;c Am;no Position Amino compound (3) . Hue ;s na~y amole diamine (6) halide compound (5) of the one of the general sulfo group formula D~NH2 173 1,3-diamino- (B) 3-B-sulfatoethyl- 4 1,5-disulfo-2-naphthylamine (neutral) benzene-4- sulfonylaniline sulfonic acid 174 ditto (B) ditto 3 ditto (greenish) 175 ditto (B) ditto 3 4-sulfoaniline (neutral~
176 ditto (B) 2-methoxy-5~B- 3 ditto (neutral) sulfatoethylsul-fonyl)-aniline 177 ditto (B) ditto 3 1,5-disulfo-2-naphthylamine (greenish) w p~
178 ditto (B) ditto 4 ditto (neutral) t~
179 ditto ~B) ditto 4 2-sulfoaniline (reddish) 18~ ditto (~) ditto 4 2,5-disulfoaniline (reddish) 181 ditto (B) 4-methoxy-5-(B- 4 ditto (reddish) sulfatoethylsuL-fonyl)-aniline 182 ditto (B) ditto 4 1,5-disulfo-2-naphthylamine (neutral) 183 ditto (B) ditto 3 ditto (greenish) 184 ditto(B) 2-methoxy-4-~B- 4 4-sulfoaniline (reddish) sulfatoethylsul-fonyl)-~hi1in~
185 ditto(B) ditto 3 - 1,5-disulfo-2-naphthylamine (greenish-) 18G dit o(B) 2-methoxy-5-methyl- 3 ditto (greenish) 4-~ -sulfatoethyl-sulfonyl)-aniline 187 ditto(B) ditto 3 4-sulfoaniline (neutral) Ex- Phenylene Cyanuric Amino Pos;tion Amino compound (3) Hue is navy ample diam;ne (6~ halide compound (5) of the one of the general sulfo group formula D-NH2 188 1,3-diamino- (B~ 2,5-dimethoxy- 3 4-sulfoaniline (neutral) benzene-4- 4- ~-sulfatoethyl-sulfonic acid sulfonyl)-aniline 189 ditto (B) ditto 3 1,5-disulfo-2-naphthylamine (greenish) 190 1,4-diamino- (B) 4-~-sulfatoethyl- 3 1,5-disulfo-2-naphthylam-ne (greenish) benzene-5- sulfonylaniline sulfonic acid 191 ditto - (B) ditto 3 4-sulfoaniline (greenish) 192 1,3-diamino- (B) ditto- 3 ditto (neutral) benzene-4~6- w disulfonic acid ?93 ditto (B) ditto 3 1,5-disulfo-2-naphthylamine (greenish) 194 1,4-diamino- (B) ditto 3 ditto (greenish) benzene-2,5-disulfonic acid 195 ditto (B) ditto 3 4-sulfoaniline (greenish) 196 1,4-diamino- ~B) ditto 3 ditto (greenish) benzene-2,6-disulfonic acicl 157 2,5-diamino- (B) ditto 3 ditto (greenish) ioluene-4-sulfonic acid 198 2,4-diamino- (B) ditto 3 ditto (reddish) toluene-5-sulfonic acid Ex- Phenylene- Cyznuric Amino Posit;on AminQ compound (3) Hue is navy am~le diamine (6) halide compound t5) of the one of the general sulfo group formula D-NH2 199 2 5-diamino- (B) 4-~-sulfato- 3 4-sulfoaniline (greenish) anisole-4- ethylsulfonyl-sulfonic acid aniline 200 2 4-diamino- (8) ditto 3 ditto (neutral) anisole-5-sulfoniç acid I
~,
11 ditto~A) ditto 3 3-carboxyaniline ~neutral) 12 ditto~A) ditto 3 4-acetylamino-2-sulfoaniline ~greenish) 13 ditto(A) ditto 3 1,5-disulTo-2-naphthylamine (greenish) 14 ditto~A) ditto 3 3,6-disulfo-2-naphthylamine ~greenish) -15 dit~o~A) ditto 3 4,8-disulfo-2-naphthylamine ~greenish) 16 ditto~A) ditto 3 3,6,8-trisulfo-2-naphthylamine ~greenish) 17 ditto~A~ ditto 3 1-sulfo-2-naphthylamine (greenish) 18 ditto(A) ditto 3 6-sulfo-2-naphthylamine ~greenish) - 19 ditto~A) ditto 3 -- 4-sulfo-1-naphthylamine (greenish) ditto~A) 4-vinylsulfonyl~ 3 4-sulfoaniline ~greenish) aniline 21 ditto(A) ditto 3 2,4-disulfoaniline ~neutral) Ex- Phenylene- Cyanuric Amino Pos;tion Am;no compound ~3) Hue is navy ample diamine t6) haL;de csmpound ~5~ of the one of the general sulfo group formula D-NH2 22 1~3-diamino- (A) 4-vinylsulfonyl- 3 2,5-disulfoaniline (greenish) benzene-4- aniline sulfonic acid 23 ditto (A) ditto 3 1,5-disulfo-2-naphthylamine (greenish) 24 ditto (A) ditio 3 3,6-disulfo-2-naphthylamine ~greenish) ditto (A) ditto 3 3,6,8-trisulfo-2-naphthylamine (greenish~
26 ditto (A3 ditto 3 1,5,7-trisulfo-2-naphthylamine (greenish) 27 ditto (A) ditto 3 4,6,8-trisulfo-2-naphthylamine (greenish) 28 ditto (A) ditto 4 4-sulfoaniline (reddish) 29 ditto (A) ditto 4 2,4-disulfoaniline (neutral) ditto (A) ditto 4 2,5-disulfoaniline (reddish) ~e 31 ditto (A) ditto 4 1 "-disulfo-2-naphthylamine (neutral) 32 ditto (A) ditto 4 3,6-disulfo-2-naphthylamine (neutral) 33 ditto (A) ditto 4 4,8-disulfo~-naphthylamine (neutral) 34 ditto (A) ditto 4 6,8-disulfo-2-naphthylamine (neutral) ditto (A) ditto 4 - 1,5,7-trisulfo-2-napthylamine (neutral) 36 ditto (A) ditto 4 3,6,8-trisulfo-2-naphthylamine (neutral) 37 ditto (A) ditto 4 4,6,8-trisulfo-2-naphthylamine (neutral~
38 ditto (A) 4-~j-sulfatoethyl- 4 - 4-sulfoaniline (reddish) - sulfonylaniline 39 ditto (A) ditto 4 2-carboxyaniline (reddish) ditto (A) ditto 4 2,4-disulfoaniline (neutral) 41 ditto ~A) ditto 4 2,5-disulfoaniline (reddish) EX- Phenylene- ~yanuric Amino Position Amino ~ompound ~3) Hue is navy - ample d;am;ne (6) halide compound (5) of the one of the general sulfo group formula D-NH2 42 1~3-diamino- (A) 4-B-sulfatoethyl- 4 2-sulfoaniline (reddish) benzene-4- sulfonylan;line - sulfonic acid 43 ditto (A) ditto 4 3-sulfoaniline (reddish) ~4 ditto (A~ ditto 4 4-carboxyaniline (neutral) ditto (A) ditto 4 4-chloro-Z-sulfoaniline (neutral) -46 ditto (A) ditto 4 4-acetylamino-2-sulfoaniline tneutral) 47 ditto (A) ditto 4 1-sulfo-2-naphthylamine (neutral) 48 ditto (A) ditto 4 6-sulfo-2-naphthylamine (neutral) 49 ditto (A) ditto 4 1,5-disulfo-2-naphthylamine (neutral) ditto (A) dittG 4 4,8-disulfo-2-naphthylamine (neutral) C~
51 ditto (A) ditto 4 6S8-disulfo-2-naphthylamine (neutral) 52 ditto (A~ ditto 4 1,5,7-trisulfo-2-naphthylamine (neutral) 53 ditto (A) ditto - 4 3,6,8-trisulfo-2-naphthylamine (neutral) 54 ditto (A) ditto 4 4-sulfo-1-naphthylamine (greenish) 1,4-diamino- (A) ditto 3 4-sulfoaniline (greenish) benzene 2-sulfonic acid 56 ditto (A) ditto 3 2,5-disulfoaniline (greenish) 57 di-t~o (A) ditto 3 4-sulfo-1-naphthylamine (greenish) 58 -ditto (A) ditto 3 1,5-disulfo-2-naphthylamine (greenish) 59 ditto (A) ditto 3 1,5,7-trisulfo-2-naphthylamine (greenish) ditto (A) ditto 3 2-sulfoaniline (greenish) Ex~ Phenylen~- ~yanuric Amino Position Amino compound ~3) Hue is navy amp~e diamine (6) halide compound (5) of ~he one of the general sulfo group formula D-NH2 61 1~3-diamino- (A) 4-~-sulfabo~ _ 3 4-sulfoaniline ~neutral) benzene-4,6- ethylsulfony~ani disulfonic acid line 6Z ditto (A) ditto 3 2,4-disulfoaniline (greenish~
63 ditto (A) ditto 3 Z-carboxyaniline (neutral) 64 ditto tA) ditto 3 4-carboxyaniline (greenish) ditto (A) ditto 3 2-chloroaniline (neutral) 66 ditto (A) ditto 3 4-chloro-2-sulfoaniline (neutral) 67 clitto (A) ditto 3 1-sulfo-2-naphthylamine (greenish) 68 ditto (A) ditto 3 1,5-disulfo-2-naphthylamine (greenish) 69 ditto (A) ditto 3 6-sulfo-2-naphthylamine (greenish) p~
ditto (A) ditto 3 Z,5-dichloro-4-sulfoaniline (greenish) 71 ditto (A) ditto 3 2,5-dimethoxy-4-sulfoaniline (sreenish) 72 1~4-diamino- (A) ditto 3 4-sulfoaniline (greenish) benzene-2,5-disulfonic acid 73 ditto (A) ditto 3 2-carboxyaniline (greenish) 74 ditto (A) ditto 3 4-carboxyaniline (greenish) ditto (A) ditto 3 2-chloroaniline (greenish) 76 ditto (A) ditto 3 2-sulfoaniline (greenish) 77 dit~o (A) ditto 3 4-sulfo-1-naphthylamine (greenish) 78 ditto (A) ditto 3 1-sulfo-2-naphthylamine (greenish) Ex- Phenylene- Cyanuric Amino Position Amino compound (3) Hue is navy ampie diamine (6) ~alide compound (5) of the one of the general sulfo sroup formula D-N~2 79 1,4-diamino- (A) 4-B-sulfato- 3 6-sulfo-2-naphthylamine (greenish) benzene-Z,S- ethylsulfonyl-disulfonic aniline acid ~0 ditto SA) ditto 3 1,5-disulfo-2-naphthylamine (greenish~
81 1,4-diamino- (A) ditto 3 4-sulfoaniline (sreenish) benzene-2,6-disulfonic acid 82 ditto(A) ditto 3 2-sulfoaniline - (greenish) 83 ditto(A) ditto 3 2-carboxyaniline (greenish) 84 ditto(A) ditto 3 2-chloroaniline (greenish) ditto(A) ditto 3 4-acetylamino-3-sulfoaniline (greenish) 86 ditto(A) ditto 3 4-sulfo-1-naphthylamine (greenish) 87 ditto~A) ditto 3 1-sulfo-2-naphthylamine (greenish) 88 ditto(A) ditto 3 6-sulfo-2-na~hthylamine (greenish) 89 ditto. (A) ditto 3 6,8-disulfo-2-naphthylamine (greenish) ditto(A) ditto 3 1,5-disulfo-2-naphthylamine (greenish) 91 1,4-diamino- (A) ditto 4 4-sulfoaniline (greenish) benzene-2-sulfonic acid 92 ditto(A) dit~o 4 2,5-disulfoaniline (greenish) 93 ditto(A) ditto 4 2-sulfoaniline (greenish) 94 ditto(A) ditto 4 1,5-disulfo-2-naphthylamine (greenish) Ex- Pheny(ene- Cyanuric Amino Posit;on Amino compound (3) Hue is navy ample diamine (6) halide compound (5) of the one of the general sulfo group formula D-NH2 95 1,4-diamino- (A) 4-~-sulfato- 4 4-sulfo-1-naphthylamine (greenish) benzene-2- ethylsulfonyl-sulfonic acid aniline 96 ditto (A) ditto 4 Z-sulfoaniline (greenish) 97 1,3-diamino- ~A) ditto 4 4-sulfoaniline (reddish) benzene-4,6- -disulfonic acid 98 ditto (A~ ditto 4 4-sulfo-1-naphthylamine (neutral) - 99 ditto (A) ditto 4 1~5-disulfo-2-naphthylamine (neutral) 100 ditto ~A) ditto 3 1-sulfo-2-naphthylamine (neutral) ~
101 ditto (A) ditto 3 2,4-disulfoaniline (reddish) Gg 102 ditto (A) ditto 3 2-chloroaniline (reddish) t~
103 1,4-diamino- (A) ditto 4 4-sulfoaniline (greenish) - benzene-2,5-disulfonic acid 104 ditto (A) ditto 4 3-sulfoaniline (neutral) 105 ditto (A) ditto 4 2-sulfoaniline (neutral) 106 ditto ~A) ditto 4 1-sulfo-2-naphthylamine (greenish) 107 ditto (A) ditto 4 - 1,5-disulfo-2-naphthylamine (greenish) 108 ditto (A) ditto 4 2-chloroaniline (neutral) 109 1,4-diamino- (A) ditto 4 4-sulfoaniline (neutral) benzene-2,6-disulTonic acid Ex- Phenylene- Cyanuric Amino Position Am;no compound (3) Hue is n2vy a~ple diamine (6) halide compound (5) of the one of the general sulfo group formula D-NH2 110 1,4-diamino- (A~ 4-~-sulfato- 4 2-sulfoaniline (neutral) benzene-2,6- ethylsulfonyl-disulfonic aniline acid 111 ditto (A) ditto 4 4-sulfo-1-naphthylamine (greenish) 112 ditto (A~ ditto 4 1,5-disulfo-Z-naphthylamine tgreenish) 113 2,5-diamino- (A~ ditto 3 4-sulfoaniline (greenish) toluene-4 ~
sulfonic acid `O
114 ditto (A) ditto 3 2-sulfoaniline (greenish) 115 ditto (A) ditto 3 1-sulfo-2-naphthylamine (greenish) 116 ditto (A) ditto 3 1,5-disulfo-2-naphthylamine (greenish) ~ç
117 2,4-diamino- (A) ditto 3 4-sulfoaniline (neutral) ~:
~oluene-5- -sulfonic acid 11~ ditto (A) ditto 3 2,5-disulfoaniline (neutral) 119 ditto ~h) ditto 3 1,5-disulfo-2-r,aphthylamine (neutral~
120 ditto (A) ditto 3 3,6-disulfo-2-naphthylamine (r,eutral) 121 Z,5-diamino- (A) ditto 3 4-sulfoaniline (greenish) anisole-4-sulfonic acid 122 d;tto (A) ditto 3 1,5-disulfo-2-naphthylamine (greenish) 123 ditto (A) ditto 3 2,5-disulfoaniline (greenish) 124 ditto (A) ditto 3 2,4-disulfoaniline (greenish) Ex- Phenylene~ ~yanuric Am;no Posit;on Amino compound (3) Hue ;s navy ample diamine (6~ halide compou~d (53 of the one of the general sulfo group formula D-NH2 12~ 2,4-diamino- tA) 4~ sulfato- 3 4-sulfoaniline ~neutral) anisole-5- ethylsulfonyi-sulfonic acid aniline 126 ditto ~A) ditto 3 1,5-disulfo-2-naphtylamine(neutral) 127 ditto (A) ditto 3 1~5,7-trisulfo-2-naphthylamine (greenish) 128 1~3-diamino- (A) 3-~-sulfato- 3 4-sulfoaniline (neutral) benzene-4- ethylsulfonyl-sulfonic acid aniline 129 ditto (A) ditto 3 2-sulfoaniline (neutral) w 130 ditto (A) ditto 3 2,4-disulfoaniline ~neutral) 131 ditto (A) ditto 3 2,5-disulfoaniline (neutral) 132 ditto (A) ditto 3 1,5-disulfo-2-naphthylamine(greenish~
133 ditto (A) ditto 3 4,8-disulfo-2-naphthylamine(greenish) 134 ditto (A) ditto 3 4-sulfo-1-naphthylamine (greenish) 135 ditto (A) 2-methoxy-4-~6-sul- 3 4-sulfoaniline (neutral) fatoethylsulfonyl)~
aniline 136 ditto (A) ditto 3 2,5-disulfoaniline (neutral) 137 ditto (A) ditto 3 4-sulfo~-naphthylamine (greenish) 138 ditto (A) ditto 3 1,5-disulfo-2-naphthylaminegreenish) 13q ditto (A) 2-methoxy-5-~-sul- 3 2-sulfoaniline (neutral) fatoethylsulfonyl~-aniline 140 ditto (A) ditto 3 2,4-disulfoaniline (neutral) 141 ditto (A) ditto 3 4-sulfo-1-llaphthylamine (greenish) Ex- Phenylene- Cyanuric Amino ~osit;on Amino conpound t3) Hue is navy ample diamine ~6) halide compound ~5) of the one of the general sulfo grGup formula D-NH2 142 1,3-diamino- (A) 2-methoxy-5- ~-sul- 3 1,5-disulfo-2-naphthylamine (greenish) benzene-4- fatoethylsulfonyL)-sulfonic acid aniline 143 ditto (A) 2-methoxy-5-methyl- 3 4-sulfoaniline (neutral) 4- ~-sulfatoethyl-sulfonyl)-aniline 144 ditto (A) ditto 3 2,5-disulfoaniline (neutral) 145 ditto (A) ditto } 4-sulfo-1-naphthylamine (greenish) 146 ditto (A) ditto 3 1,4-disulfo-2-naphthylamine (sreenish) 147 ditto (A) 2,5-dimethoxy-4- 3 2-sulfoaniline (neutral) ~-sulf~toethylsul- ~
fonyl) aniline CD
14~ ditto (A) ditto 3 4-sulfoaniline (neutral) 149 dit~o (A~ ditto 3 2,5-disulfoaniline (neutral) 2 150 ditto (A3 ditto 3 1,5 disulfo-2-naphthylamine (greenish) 151 ditto (A) ditto 3 - 4-sulfo-1-naphthylamine (greenish) 152 ditto ~A) 2-methoxy-5-chloro- 3 2-sulfoaniline (neutral) 4- ~-sulfatoethyl-sulfonyl)-aniline 153 ditto (A) ditto 3 4-sulfo-1-naphthylamine (sreenish) 154 ditto (A) ditto 3 -- 2,5-disulfoaniline (neut al) 155 ditto (A) ditto 3 1,5-disulfo-2-naphthylamine (greenish) 156 ditto (A) 4-methoxy-5- ~-sul- 3 4-sulfoaniline (neutral) fatoethylsulfonyl)-aniline Ex~ Phenylene Syanuric Amino Position Amino compound (3) Hue ;s navy ample diamine (6~ halide compound (5) of the one of the general sulfo group formula D-NH2 157 1,3-di am ino- (A) 4-methoY~y-S- ~- 3 2-sulfoaniline (neutral) benzene-4- sulfatoethylsul~
sulfonic acid fonyl)-aniline 158 ditto (A) ditto 3 2,5-disulfoaniline (neutral) 159 ditto (A) ditto 3 1,5-disulfo-2-naphthylamine (greenish) 160 ditto (A) 2-methoxy-5- ~- 4 2-sulfoaniline (neutral) sulfatoetnylsul-fonyl)-aniline 161 ditto (A) ditto 4 2,4-disulfoaniline (neutral) 162 ditto (A) ditto 4 1,5-disulfo-2-naphthylamine (neutral) 163 di~to (A) ditto 4 4-sulfo-1-naphthylamine (greenish) 164 ditto (A) 2-methoxy-5-vinyl- 4 2,5-disulfoaniline (reddish) ~
sulfonylaniline ~`
165 ditto (A) ditto 4 1,5-disulfo-2-naphthylamine (neutral) 166 ditto (B) 4-~3-sulfatoethyl- 3 4-sulfoaniline (neutral) sulfonylaniline 167 ditto . (B) ditto 3 1j5-disulfo-2-naphthylamine (greenish) 168 ditto (B) 4-vinylsuifonyl- 3 2,5-disulfoaniline (neutral) aniline 169 ditto (B) ditto 4 ditto (reddish) 170 ditto (8) ditto 4 4-sulfoaniline (reddish) 171 ditto (B) ditto 4 1,5-disulfo-2-naphthylamine (neutral) 172 ditto (B, 3-6-sulfatoethyl- 4 2-sulfoaniline (reddish) sulfonylaniline Ex- Phenylene- Cyanur;c Am;no Position Amino compound (3) . Hue ;s na~y amole diamine (6) halide compound (5) of the one of the general sulfo group formula D~NH2 173 1,3-diamino- (B) 3-B-sulfatoethyl- 4 1,5-disulfo-2-naphthylamine (neutral) benzene-4- sulfonylaniline sulfonic acid 174 ditto (B) ditto 3 ditto (greenish) 175 ditto (B) ditto 3 4-sulfoaniline (neutral~
176 ditto (B) 2-methoxy-5~B- 3 ditto (neutral) sulfatoethylsul-fonyl)-aniline 177 ditto (B) ditto 3 1,5-disulfo-2-naphthylamine (greenish) w p~
178 ditto (B) ditto 4 ditto (neutral) t~
179 ditto ~B) ditto 4 2-sulfoaniline (reddish) 18~ ditto (~) ditto 4 2,5-disulfoaniline (reddish) 181 ditto (B) 4-methoxy-5-(B- 4 ditto (reddish) sulfatoethylsuL-fonyl)-aniline 182 ditto (B) ditto 4 1,5-disulfo-2-naphthylamine (neutral) 183 ditto (B) ditto 3 ditto (greenish) 184 ditto(B) 2-methoxy-4-~B- 4 4-sulfoaniline (reddish) sulfatoethylsul-fonyl)-~hi1in~
185 ditto(B) ditto 3 - 1,5-disulfo-2-naphthylamine (greenish-) 18G dit o(B) 2-methoxy-5-methyl- 3 ditto (greenish) 4-~ -sulfatoethyl-sulfonyl)-aniline 187 ditto(B) ditto 3 4-sulfoaniline (neutral) Ex- Phenylene Cyanuric Amino Pos;tion Amino compound (3) Hue is navy ample diam;ne (6~ halide compound (5) of the one of the general sulfo group formula D-NH2 188 1,3-diamino- (B~ 2,5-dimethoxy- 3 4-sulfoaniline (neutral) benzene-4- 4- ~-sulfatoethyl-sulfonic acid sulfonyl)-aniline 189 ditto (B) ditto 3 1,5-disulfo-2-naphthylamine (greenish) 190 1,4-diamino- (B) 4-~-sulfatoethyl- 3 1,5-disulfo-2-naphthylam-ne (greenish) benzene-5- sulfonylaniline sulfonic acid 191 ditto - (B) ditto 3 4-sulfoaniline (greenish) 192 1,3-diamino- (B) ditto- 3 ditto (neutral) benzene-4~6- w disulfonic acid ?93 ditto (B) ditto 3 1,5-disulfo-2-naphthylamine (greenish) 194 1,4-diamino- (B) ditto 3 ditto (greenish) benzene-2,5-disulfonic acid 195 ditto (B) ditto 3 4-sulfoaniline (greenish) 196 1,4-diamino- ~B) ditto 3 ditto (greenish) benzene-2,6-disulfonic acicl 157 2,5-diamino- (B) ditto 3 ditto (greenish) ioluene-4-sulfonic acid 198 2,4-diamino- (B) ditto 3 ditto (reddish) toluene-5-sulfonic acid Ex- Phenylene- Cyznuric Amino Posit;on AminQ compound (3) Hue is navy am~le diamine (6) halide compound t5) of the one of the general sulfo group formula D-NH2 199 2 5-diamino- (B) 4-~-sulfato- 3 4-sulfoaniline (greenish) anisole-4- ethylsulfonyl-sulfonic acid aniline 200 2 4-diamino- (8) ditto 3 ditto (neutral) anisole-5-sulfoniç acid I
~,
Claims (28)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A water-soluble disazo compound of the formula (1) in which R1 and R2, identical to or different from each other, are each a hydrogen atom, an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms or a chlorine atom, R is a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms or a sulfo group, M is a hydrogen atom or the equivalent of a metal, X is vinyl or .beta.-sulfatoethyl group, Y is a chlorine atom or a fluorine atom with the proviso that, if Y is chlorine, D is a phenyl radical which can be substituted by 1, 2 or 3 substituents from the group consisting of carboxy, sulfo alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, trichloromethyl, trifluoromethyl, nitro, alkanoylamino having 1 to 4 carbon atoms in the alkyl radical, benzoylamino which can be substituted in the benzene nucleus by one or two substituents from the group consisting of methyl, ethyl, methoxy ethoxy, chlorine and sulfo, phenylsulfonylamino which can be substituted by one or two substituents from the group consisting of methyl, ethyl, methoxy and ethoxy, or D is a naphthyl radical which is substituted by 1, 2 or 3 sulfo groups, and if Y is fluorine, D is phenyl unsubstituted or substituted by 1, 2 or 3 substituents selected from the group consisting of carboxy, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, trichloromethyl, trifluoromethyl, nitro, alkanoylamino having 1 to 4 carbon atoms in the alkyl moiety, benzoylamino unsubstituted or substituted in the benzene nucleus by 1 or 2 substituents selected from the group consisting of methyl, ethyl, methoxy, ethoxy, chlorine and sulfo, and phenylsulfonylamino unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of methyl, ethyl, methoxy and ethoxy, or D is naphthyl substituted by 1, 2 or 3 sulfo groups, and the moieties R1, R2, R, Y and the substituents in D can be identical to or different from one another, provided that in compounds in which the triazinylamino radical is bonded to the benzene nucleus in the meta-position to the azo group and in the para-position to the sulfo group -SO3M and R is hydrogen, then D is not 5-sulfo-naphth-1-yl, 1,5-disulfo-naphth-2-yl, 4,8-disulfo-naphth-2--yl, 1-sulfo-naphth-2-yl nor 3,6,8-trisulfo-naphth-2-yl.
2. A water-soluble disazo compound of the formula (1) in which R1 and R2, identical to or different from each other, are each a hydrogen atom, an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms or a chlorine atom, R is a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms or a sulfo group, M is a hydrogen atom or the equivalent of a metal, X is vinyl or .beta.-sulfatoethyl group, Y is a chlorine atom or a fluorine atom with the proviso that, if Y is chlorine, D is a phenyl radical which can be substituted by 1, 2 or 3 substituents from the group consisting of carboxy, sulfo, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, trichloromethyl, trifluoromethyl, nitro, alkanoylamino having 1 to 4 carbon atoms in the alkyl radical, benzoylamino which can be substituted in the benzene nucleus by one or two substituents from the group consisting of methyl, ethyl, methoxy, ethoxy, chlorine and sulfo, phenylsulfonylamino which can be substituted by one or two substituents from the group consisting of methyl, ethyl, methoxy and ethoxy, or D is a naphthyl radical which is substituted by 1, 2 or 3 sulfo groups, if Y is fluorine, D is monosulfophenyl or is naphthyl substituted by 1, 2 or 3 sulfo groups and the moieties R1, R2, R, Y and the substituents in D can be identical to or different from one another.
3. A disazo compound as claimed in claim 1 or 2 of the formula (1) in which Y is chlorine and D contains at least one sulfo group or carboxy group as substituent.
4. A disazo compound as claimed in claim 1 of the formula (1) in which D is a phenyl radical which is substituted by one, two or three substituents which are selected from the group consisting of 2 alkoxy groups of 1 to 4 carbon atoms, 2 alkyl groups of 1 to 4 carbon atoms, 2 chlorine atoms, 1 bromine atom, 1 fluorine atom, 1 trichloromethyl group, 1 trifluoromethyl group, 1 alkanoylamino group having 1 to 4 carbon atoms in the alkyl radical, 1 nitro group, 1 carboxy group and 2 sulfo groups, and Y is chlorine.
5. A disazo compound as claimed in claim 1 of the formula (1), in which D is a phenyl radical which is substituted by 1, 2 or 3 substituents selected from the group consisting of 2 alkoxy groups, 2 chlorine atoms, 2 sulfo groups, 1 carboxy group, 1 nitro group, 1 alkyl group of 1 to 4 carbon atoms and 1 acetylamino group, and Y is chlorine.
6. A disazo compound as claimed in claim 1 of the formula (1), in which D is a phenyl radical which is substituted by one or two sulfo groups, and Y is chlorine.
7. A disazo compound as claimed in claim 1 of the formula (I) in which D is a naphthyl radical which is substituted by 1, 2 or 3 sulfo groups.
8. A disazo compound as claimed in claim 1, 5 or 6 in which R1 is a hydrogen atom, a methyl group, a methoxy group or a chlorine atom and R2 is a hydrogen atom, a methyl group or a methoxy group.
9. A disazo compound as claimed in claim 7, in which R1 is a hydrogen atom, a methyl group, a methoxy group or a chlorine atom and R2 is a hydrogen atom, a methyl group or a methoxy group.
10. A disazo compound as claimed in claim 1, 5 or 9, in which R is a hydrogen atom or a sulfo group.
11. A disazo compound as claimed in claim 1 of the formula in which -SO2-X is bonded in the m- or p-position and M and X have the meanings mentioned in claim 1.
12. A disazo compound as claimed in claim 1, 5 or 7, in which the group -SO2-X is bonded to the benzene nucleus in para-position relative to the amino group.
13. A disazo compound as claimed in claim 1 of the formula in which M and X have the meanings mentioned in claim 1.
14. A disazo compound as claimed in claim 1 of the formula in which X and M have the meanings mentioned in claim 1 and D is the 4-sulfophenyl group.
15. A disazo compound as claimed in claim 11 or 14, in which the group -SO2-X is bonded to the benzene nucleus in para-position relative to the amino group.
16. A disazo compound as claimed in claim 14, in which D is the 2,4-disulfophenyl group.
17. A disazo compound as claimed in claim 14, in which D is the 1,5-disulfo-2-naphthyl group.
18. A disazo compound as claimed in claim 14, in which D is the 4-sulfo-1-naphthyl group.
19. A disazo compound as claimed in claim 1, 5 or 7 in which the moiety X is a .beta.-sulfatoethyl group.
20. A disazo compound as claimed in claim 1, 5 or 7 in which the moiety X is a vinyl group.
21. A disazo compound as claimed in claim 1, 5 or 7 in which M is hydrogen, sodium or potassium.
22. A disazo compound as claimed in claim 11, 13 or 14, in which the moiety X is a .beta.-sulfatoethyl group.
23. A disazo compound according to claim 1 or 2 which is a compound of formula 1 as defined in claim 1 or 2, other than a compound in which D is a sulfo-naphthyl group, R is hydrogen and the triazinylamino radical is bonded to the benzene nucleus in the meta-position to the azo group and in the para-position to the sulfo group -SO3M.
24. A process for preparing a disazo compound of claim 1, which comprises coupling a monoazo compound of the formula (2) in which R1, R2, R, D, M, Y and X have the meanings mentioned in claim 1, with the diazonium salt of an amino compound of the formula (3) H2N - D (3) in which D has the meaning mentioned in claim 1.
25. A process for dyeing hydroxy- and carboxamide-containing material in which the dyestuff used is a disazo compound of formula (1) as defined in claim 1.
26. A process as claimed in claim 25 wherein the hydroxy-and carboxamide-containing material is a fiber material.
27. A process for dyeing hydroxy- and carboxamide-containing material in which a dyestuff is applied onto or into the material and fixed under heat and/or with the aid of an acid-binding agent, which comprises using as dyestuff a compound of formula (1) as defined in claim 1.
28. A process as claimed in claim 27 wherein the hydroxy-and carboxamide-containing material is a fiber material.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3217388.1 | 1982-05-08 | ||
| DE19823217388 DE3217388A1 (en) | 1982-05-08 | 1982-05-08 | WATER-SOLUBLE DISAZO COMPOUNDS, METHOD FOR THEIR PRODUCTION AND THEIR USE AS DYES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1199632A true CA1199632A (en) | 1986-01-21 |
Family
ID=6163107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000427666A Expired CA1199632A (en) | 1982-05-08 | 1983-05-06 | Water-soluble disazo compounds |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0094020B1 (en) |
| JP (1) | JPS58204053A (en) |
| KR (1) | KR910007080B1 (en) |
| AR (1) | AR241197A1 (en) |
| BR (1) | BR8302387A (en) |
| CA (1) | CA1199632A (en) |
| DE (2) | DE3217388A1 (en) |
| IN (1) | IN158270B (en) |
| MX (1) | MX155941A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104312205A (en) * | 2014-10-13 | 2015-01-28 | 天津德凯化工股份有限公司 | Red activated dye |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3420467A1 (en) * | 1984-06-01 | 1985-12-05 | Basf Ag, 6700 Ludwigshafen | REACTIVE DYES |
| DE3517755A1 (en) * | 1985-05-17 | 1987-01-15 | Hoechst Ag | WATER-SOLUBLE MONO AND DISAZO COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS DYES |
| KR100368987B1 (en) * | 2000-11-20 | 2003-01-24 | 이화산업 주식회사 | Reactive black dyestuff composition |
| KR100427549B1 (en) * | 2002-02-19 | 2004-04-28 | 이화산업 주식회사 | Reactive black dye composition |
| CN102317378B (en) | 2009-02-18 | 2015-08-19 | 司色艾印染科技（上海）有限公司 | Fluorine containing reactive dyes |
| CN104327542A (en) * | 2014-10-13 | 2015-02-04 | 天津德凯化工股份有限公司 | Red reactive dye and its preparation method |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2842640A1 (en) * | 1978-09-29 | 1980-04-10 | Bayer Ag | REACTIVE DYES |
| JPS56128380A (en) * | 1980-03-14 | 1981-10-07 | Sumitomo Chemical Co | Dyeing of cellulosic fiber |
| JPS57167462A (en) * | 1981-04-07 | 1982-10-15 | Sumitomo Chemical Co | Dyeing of cellulosic fiber |
-
1982
- 1982-05-08 DE DE19823217388 patent/DE3217388A1/en not_active Withdrawn
-
1983
- 1983-05-02 IN IN533/CAL/83A patent/IN158270B/en unknown
- 1983-05-04 EP EP83104368A patent/EP0094020B1/en not_active Expired
- 1983-05-04 DE DE8383104368T patent/DE3365997D1/en not_active Expired
- 1983-05-06 AR AR83292951A patent/AR241197A1/en active
- 1983-05-06 JP JP58078382A patent/JPS58204053A/en active Pending
- 1983-05-06 CA CA000427666A patent/CA1199632A/en not_active Expired
- 1983-05-06 KR KR1019830001925A patent/KR910007080B1/en not_active IP Right Cessation
- 1983-05-06 MX MX197195A patent/MX155941A/en unknown
- 1983-05-06 BR BR8302387A patent/BR8302387A/en not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104312205A (en) * | 2014-10-13 | 2015-01-28 | 天津德凯化工股份有限公司 | Red activated dye |
Also Published As
| Publication number | Publication date |
|---|---|
| KR840004765A (en) | 1984-10-24 |
| DE3365997D1 (en) | 1986-10-16 |
| EP0094020B1 (en) | 1986-09-10 |
| DE3217388A1 (en) | 1983-11-17 |
| KR910007080B1 (en) | 1991-09-16 |
| EP0094020A1 (en) | 1983-11-16 |
| BR8302387A (en) | 1984-01-10 |
| IN158270B (en) | 1986-10-11 |
| MX155941A (en) | 1988-05-25 |
| JPS58204053A (en) | 1983-11-28 |
| AR241197A1 (en) | 1992-01-31 |
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