Water-soluble disazo dyestuffs

With the present invention, novel water-soluble dyestuffs of the general formula (1) ##STR1## and their heavy metal complex compounds have been found.
The novel dyestuffs of the formula (1) can be in the form of the free acid or in the form of their salts. They are preferably in the form of the salts, especially the alkali metal and alkaline earth metal salts and in particular in the form of the sodium, potassium and calcium salts. They are preferably used in the form of the alkali metal salts for dyeing and printing fiber materials.
In the above formula (1), the various radicals in the formula have the following meaning: K.sub.1 and K.sub.2 are identical or different, preferably identical, and, described in the form of the free acid, represent a radical of the general formula ##STR2## in which R denotes a hydrogen atom or a lower alkyl group, such as a methyl group, and p denotes the number 1 or 2, preferably one of the radicals of the formulae ##STR3## the above radicals K.sub.1 and K.sub.2 in the formula being bonded via the amino groups to the s-triazine radicals and in the ortho-position relative to the hydroxy groups to the azo groups; D is a benzene nucleus or naphthalene nucleus; R.sub.1 is in the ortho-position relative to the azo group and denotes a hydrogen atom, a halogen atom, preferably a chlorine or bromine atom, a lower alkyl group, preferably a methyl group, a lower alkoxy group, preferably a methoxy group, a hydroxy or carboxy group or a sulfonic acid group and R.sub.2 is a hydrogen atom, a halogen atom, preferably a chlorine or bromine atom, a lower alkyl group, preferably a methyl group, a lower alkoxy group, preferably a methoxy group, a nitro group or a sulfonic acid group, it being possible for R.sub.1 and R.sub.2 to be identical or different from one another; X represents the .beta.-thiosulfatoethyl or .beta.-chloroethyl group, preferably the .beta.-sulfatoethyl or vinyl group; A is an aliphatic radical of 2-10 C atoms, especially an alkylene radical of 2-6 C atoms, or an aliphatic radical, especially an alkylene radical, of, in total, 2-6 C atoms, which can be interrupted by hetero-atoms and/or cycloaliphatic radicals, for example by 1 or 2 such members from the group comprising --NH--, --O-- and --N(CH.sub.3)-- and/or by a sulfur atom or a cyclohexylene group, or is a cycloaliphatic radical, such as, for example, a cyclohexylene radical, which can also be substituted by 1-3 methyl groups, or is a benzene nucleus or a naphthalene nucleus, which can also be substituted by substituents from the group comprising lower alkyl, such as, for example, methyl or ethyl, lower alkoxy, such as, for example, methoxy and ethoxy, chlorine, sulfo, carboxy and lower alkanoylamino, such as acetylamino, or is one of the radicals of the formulae ##STR4## in which the benzene nuclei can be substituted by substituents, preferably 1 or 2 substituents, from the group comprising lower alkyl, such as methyl, lower alkoxy, such as methoxy, sulfo, carboxy and chlorine, and in which D.sub.1 is a direct covalent bond or a bridge member, for example a bridge member of the formulae --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --, --O--CH.sub.2 --CH.sub.2 --O--, --CH.dbd.CH--, --NH--, --O--, --S--, --SO.sub.2 --, --N.dbd.N--, --NH--CO--NH--, --CO--NH--, --NH--CO--, ##STR5## of a cyclohexylene radical, especially a radical of the formula ##STR6## preferably a bridge member of the formula --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH--, --NH--, --SO.sub.2 --, --CO--NH-- or --NH--CO-- or the abovementioned bivalent radical of oxadiazole or preferably a direct covalent bond, and E represents a member of the formula --O--, --S--, --NH--, or --SO.sub.2 --; and Y is a chlorine, fluorine or bromine atom or a sulfonic acid group or a group which consists of a substituent bonded via a sulfur or oxygen atom and is of the formula --S--R' or --O--R", in which R' is preferably a substituent from the group comprising lower alkyl, substituted lower alkyl, phenyl, naphthyl, substituted phenyl, substituted naphthyl or 2-benzthiazolyl, such as, for example, lower alkyl substituted by substituents from the group comprising hydroxy, lower alkoxy, sulfato, sulfo, carboxy, phenyl, naphthyl, substituted phenyl and substituted naphthyl, or, for example, phenyl or naphthyl substituted by substituents from the group comprising nitro, sulfo and carboxy, and R" denotes a hydrogen atom or has the meaning of R' with the exception of 2-benzthiazolyl, or Y is an amino group of the formula --NR.sub.3 R.sub.4, in which R.sub.3 is a hydrogen atom, an optionally substituted lower aliphatic radical or an optionally substituted araliphatic radical or a cycloaliphatic radical, such as, for example, a lower alkyl radical which can be substituted by one or two substituents from the group comprising hydroxy, sulfato, lower alkoxy, sulfo, carboxy and phenyl, or is a cyclohexyl radical, and R.sub.4 represents a hydrogen atom, an optionally substituted lower aliphatic radical, such as, for example, a lower alkyl radical which can be substituted by hydroxy, lower alkoxy, sulfato, sulfo and carboxy, or represents an optionally substituted aromatic radical, such as, for example, a phenyl or naphthyl radical, which can be substituted by one or two substituents from the group comprising hydroxy, carboxy, sulfo, lower alkyl and lower alkoxy, or represents an optionally substituted araliphatic radical, such as, for example, a lower alkyl radical which can be substituted by phenyl or naphthyl, or represents a hydroxy group or a lower alkoxy group or represents an optionally substituted amino group, such as, for example, the amino group or a phenylamino or lower alkylamino group, or in which R.sub.3 and R.sub.4 together with the nitrogen atom form a ring containing a lower alkylene radical and optionally a hetero-atom, such as, for example, a nitrogen atom or oxygen atom, such as, for example a morpholine, piperidine or piperazine ring.
The two radicals ##STR7## in the formula can be identical or different in the general formula (1); preferably they are identical.
Here and in the text which follows, the term "lower" used in the definitions denotes that the alkyl or alkylene radical contained in the group consists of 1-4 C atoms.
The present invention also relates to heavy metal complex dyestuffs of the abovementioned formula (1), in which one or both of the R.sub.1 s represents a hydroxyl group and bond the metal as a complex with the hydroxy groups of the coupling component or components. The heavy metal complex dyestuffs are preferably those in which two heavy metal equivalents are each bonded in complex form to one molecule of the formula (1), specifically in each case to the hydroxy groups R.sub.1 and those of the aminonaphthol-disulfonic acid radicals. Preferred heavy metal complex dyestuffs are the copper, cobalt and chromium complex dyestuffs of the formula (1) according to the invention, especially the copper complex dyestuffs.
The present invention also relates to a process for the manufacture of the novel dyestuffs of the formula (1), which comprises reacting 2 moles of the diazonium compound of one or two aromatic amines, preferably a single aromatic amine of the general formula (2) ##STR8## in which D, R.sub.1, R.sub.2 and X are as defined above and R.sub.1 is in the ortho-position relative to the amino group, with 1 mole of a coupling component of the general formula (3) ##STR9## in which A, K.sub.1, K.sub.2 and Y are as defined above.
The present invention also relates to a process for the manufacture of the heavy metal complex dyestuffs of the abovementioned general formula (1), which comprises reacting the metal-free dyestuffs of the formula (1) in which R.sub.1 represents a hydrogen atom or a hydroxy or lower alkoxy group, if desired immediately following the abovementioned procedure, according to the invention, for the manufacture of the metal-free dyestuffs of the formula (1), in a manner which is in itself known, if appropriate in the presence of an oxidizing agent, with a metal donor.
The metal-free dyestuffs of the formula (1) or their heavy metal complexes can, however, also be manufactured in a manner according to the invention by subjecting one mole of each of the monoazo compounds of the general formulae (4) and (5) ##STR10## described in the form of the free acids, in which R.sub.1, R.sub.2, D and X are as defined above and K.sub.3 and K.sub.4 are identical or different, preferably identical, and represent a radical of the general formula ##STR11## in which R and p are as defined above, and preferably represent one of the radicals of the formulae ##STR12## the azo group being bonded to the radicals K.sub.3 and K.sub.4 in formulae 4 and 5 in each case in the ortho-position relative to the hydroxy group of the naphthol radical, or two moles of their heavy metal complex compounds in which R.sub.1 is a hydroxy group, preferably the 1:1 copper complex compounds, or 1 mole of the heavy metal complex compound of the formula (4) or (5) and 1 mole of the metal-free compound of the formula (5) or, respectively, (4) to a condensation reaction with a halogeno-s-triazine compound of the formula (6) ##STR13## in which A and Y are as defined above and Hal represents a chlorine, bromine or fluorine atom, and, if desired, subsequently reacting the product in a manner which is in itself known, if appropriate in the presence of an oxidizing agent, with an agent which donates a heavy metal cation.
The novel metal-free or metal-containing dyestuffs of the formula (1) in which K.sub.1 and K.sub.2 are identical can also be manufactured in a manner according to the invention by subjecting 2 moles of a monoazo compound of the formula (7) ##STR14## in which D, R.sub.1, R.sub.2, X, Y and Hal are as defined above and K.sub.1 represents one of the abovementioned radicals, which is identical to K.sub.2, to a condensation reaction with one mole of a compound of the formula (8)
H.sub.2 N--A--NH.sub.2 ( 8)
in which A is as defined above, and, if desired, reacting the metal-free dyestuff of the formula (1), thus obtained, in a manner which is in itself known, if appropriate in the presence of an oxidizing agent, with a metal donor.
The abovementioned condensation reactions are preferably carried out in aqueous solution, optionally in the presence of organic solvents, at room temperature (15.degree.-25.degree. C.) or elevated temperature (up to 120.degree. C.) in accordance with known processes in an analogous manner well known to those skilled in the art. If the heavy metal complex dyestuffs according to the invention are manufactured by subsequent metallization, as indicated here, one or both of the R.sub.1 s can be a hydrogen atom, a hydroxy group or a lower alkoxy group.
It is also possible, in a manner according to the invention, to convert a heavy metal complex dyestuff according to formula (1) into a heavy metal dyestuff according to the invention which contains a different heavy metal central atom, by splitting the original heavy metal atom from the complex dyestuff analogously to the known methods (see, for example, Angew. Chem. 64, 397 (1952)) and reacting the resulting o,o'-dihydroxy-azo dyestuff with an agent which supplies the other heavy metal atom. Thus, for example, copper complex dyestuffs of the formula (1) can be converted to the corresponding chromium or cobalt complex dyestuffs of the formula (1).
Preferred dyestuffs, according to the invention, of the formula (1) and their heavy metal complexes are those in which D represents a benzene nucleus and also those in which D represents a naphthalene nucleus in which the azo group is bonded in the .beta.-position of this naphthalene nucleus. Further preferred dyestuffs according to the invention are those in which Y denotes a halogen atom, preferably a chlorine atom. Furthermore, dyestuffs of particular importance are those in which K.sub.1 and K.sub.2, which can be identical or different, represent the abovementioned divalent radical of 1-amino-naphthol(8)-3,6-disulfonic acid, 1-aminonaphthol(8)-4,6-disulfonic acid, 2-amino-naphthol(8)-6-sulfonic acid or 2-amino-naphthol(5)-7-sulfonic acid.
In addition to the said halogen atoms and the sulfonic acid group, the following individual groups are to be singled out for the substituent Y in the triazine ring of the dyestuffs of the formula (1) or of the compounds of the formulae (3), (6) and (7):
--O--CH.sub.3, --O--C.sub.2 H.sub.5, --O--CH.sub.2 --CH.sub.2 --CH.sub.3, --OH, ##STR15## --S--CH.sub.2 --CH.sub.2 --OH, ##STR16## --S--CH.sub.2 --COOH, ##STR17## --NH.sub.2, --NH--CH.sub.3, --NHC.sub.2 H.sub.5, --NHC.sub.3 H.sub.7, ##STR18## --NH--CH.sub.2 --CH.sub.2 --OH, --NH--CH.sub.2 --CH.sub.2 --OSO.sub.3 H, --NH--CH.sub.2 --CH.sub.2 --O--CH.sub.3, ##STR19## --NH--CH.sub.2 --CH.sub.2 --SO.sub.3 H, --NH--CH.sub.2 --COOH, ##STR20## --NH--OH, --NH--NH.sub.2, ##STR21##
Preferably, the radical Y in the formula denotes a chlorine, bromine or fluorine atom or a sulfo, amino, methylamino, dimethylamino, .beta.-hydroxyethyl-amino, .beta.-methoxyethyl-amino, .beta.-sulfatoethyl-amino, .beta.-sulfoethyl-amino, N-methyl-N-.beta.-sulfoethyl-amino, carboxymethyl-amino, N-.beta.-carboxyethyl-amino, N-(carboxyphenyl)-amino, N-(sulfophenyl)-amino, N-(disulfo-phenyl)-amino, N-(sulfonaphthyl(1))-amino, N-methylanilino, morpholino, iso-propoxy, phenoxy or .beta.-hydroxyethylthioether group.
Further compounds of the formula (1) which should be mentioned as being preferred are those in which D is a benzene nucleus and R.sub.1, R.sub.2, A, K.sub.1, K.sub.2, Y and X have one of the abovementioned meanings, especially the preferred meanings, and also compounds of the formula (1) in which D denotes a naphthalene nucleus which is bonded in the 2-position to the azo group, R.sub.1 represents a hydrogen atom and R.sub.2 represents the sulfo group in the 6-position of the naphthalene nucleus, or R.sub.1 denotes the sulfo group and R.sub.2 is hydrogen, and K.sub.1, K.sub.2, A, Y and X have one of the abovementioned meanings, especially the preferred meanings.
Further preferred compounds of the formula (1) are those in which D represents a benzene nucleus, in which the group --SO.sub.2 --X is in the meta-position or para-position relative to the azo group, or in which D denotes a naphthalene nucleus which is bonded in the 2-position to the azo group and which contains the group --SO.sub.2 --X in the 6-position or 8-position, and A, R.sub.1, R.sub.2, K.sub.1, K.sub.2, Y and X have one of the abovementioned meanings, especially the preferred meanings.
Further compounds to be singled out are those in which A represents a radical of the formula ##STR22##
Further preferred compounds of the formula (1) to be mentioned are those in which D, R.sub.1, R.sub.2 and A have one of the abovementioned meanings, especially the preferred meanings, X represents the .beta.-sulfatoethyl radical and Y represents a chlorine atom and K.sub.1 denotes a radical of the formula ##STR23## and K.sub.2 denotes a radical of the formula ##STR24## Amongst these compounds, compounds in which D is a benzene nucleus, R.sub.1 and R.sub.2 are each hydrogen, and the .beta.-sulfatoethylsulfonyl group is in the p-position relative to the azo group, are particularly preferred.
The aromatic amines of the formula (2) are known, for example from German Patent Specifications 1,278,041, 1,276,842, 1,150,163, 1,126,542 and 1,153,029, from German Offenlegungsschriften 2,154,943, 2,100,080, 2,049,664, 2,142,728, 2,034,591 and 1,943,904 or from German Auslegeschrift 1,204,666.
Aromatic amines of the formula (2) which may be mentioned are, in particular, the following compounds: aniline-3-.beta.-sulfatoethylsulfone, aniline-4-.beta.-sulfatoethylsulfone, 2-amino-toluene-4-.beta.-sulfatoethylsulfone, 2-amino-anisole-4-.beta.-sulfatoethylsulfone, 2-amino-anisole-5-.beta.-sulfatoethylsulfone, 2-amino-4-.beta.-sulfatoethylsulfonyl-benzoic acid, 2-methoxy-5-methyl-aniline-4-.beta.-sulfatoethylsulfone, 2,5-dimethoxy-aniline-4-.beta.-sulfatoethylsulfone, 2,4-dimethoxy-aniline-5-.beta.-sulfatoethylsulfone, 4-aminoanisole-2-.beta.-sulfatoethylsulfone, 4-aminotoluene-2-.beta.-sulfatoethylsulfone, 4-.beta.-sulfatoethylsulfonyl-aniline-2-sulfonic acid, 5-.beta.-sulfatoethylsulfonyl-aniline-2-sulfonic acid, 2-chloroaniline-4-.beta.-sulfatoethylsulfone, 2-chloroaniline-5-.beta.-sulfatoethylsulfone, 2-bromoaniline-4-.beta.-sulfatoethylsulfone, 2,6-dichloroaniline-4-.beta.-sulfatoethylsulfone, 2,6-dimethyl-aniline-4-.beta.-sulfatoethylsulfone, 2,6-dimethyl-aniline-3-.beta.-sulfatoethylsulfone, 2-amino-phenol-4-.beta.-sulfatoethylsulfone, 2-amino-phenol-5-.beta.-sulfatoethylsulfone, 6-bromo-2-amino-phenol-4-.beta.-sulfatoethylsulfone, 6-chloro-2-amino-phenol-4-.beta.-sulfatoethylsulfone, 6-nitro-2-amino-phenol-4-.beta.-sulfatoethylsulfone, 4-methyl-2-amino-phenol-5-.beta.-sulfatoethylsulfone, 2-naphthylamine-5-.beta.-sulfatoethylsulfone, 2-naphthylamine-8-.beta.-sulfatoethylsulfone, 8-.beta.-sulfatoethylsulfonyl-2-amino-naphthalene-6-sulfonic acid, 6-.beta.-sulfatoethylsulfonyl-2-amino-naphthalene-1-sulfonic acid, 2-naphthylamine-6-.beta.-sulfatoethylsulfone and the corresponding vinylsulfonyl, .beta.-thiosulfatoethylsulfonyl and .beta.-chloroethylsulfonyl compounds.
The coupling components of the formula (3) can, for example, easily be prepared in a manner which is analogous to the procedures described in German Patent Specification 485,185 and which is well-known to those skilled in the art. Coupling components of the formula (3) which may be mentioned are, in particular, the compounds of the formula (3) which are listed in the following table and in which A and Y have one of the abovementioned meanings:
______________________________________Coupling components of the formula (3):HK.sub.1 K.sub.2H______________________________________ ##STR25## ##STR26## ##STR27## ##STR28## "" ##STR29## ##STR30## ##STR31##" ##STR32## ##STR33## "" ##STR34##" ##STR35##" ##STR36## ##STR37## "" ##STR38##" ##STR39## ##STR40## "" ##STR41## ##STR42## "" ##STR43##" ##STR44## ##STR45## "" ##STR46## ##STR47## ##STR48## ##STR49## " ##STR50## "" ##STR51## ##STR52## " ##STR53## " ##STR54## "" ##STR55##" ##STR56## ##STR57## " ##STR58## " ##STR59## " ##STR60## ##STR61## ##STR62## " ##STR63## "" ##STR64## ##STR65## " ##STR66## " ##STR67## ##STR68## ##STR69## " ##STR70## " ##STR71## "" ##STR72## ##STR73## ##STR74## ##STR75## "" ##STR76## ##STR77## "" ##STR78## ##STR79## ##STR80## ##STR81## " ##STR82## ##STR83##" ##STR84## ##STR85## "" ##STR86##" ##STR87## ##STR88## "" ##STR89## ##STR90## "" ##STR91## ##STR92## " ##STR93## ##STR94##" ##STR95## ##STR96## "" ##STR97## ##STR98## "" ##STR99##" ##STR100##______________________________________
The diazotization of the aromatic amines of the formula (2) is carried out by generally known methods. However, care must be taken that these aromatic amines, and the diazonium salts obtained therefrom, are not subjected to strongly alkaline conditions during processing.
The coupling of the diazotized amines with the coupling components of the formula (3) is preferably carried out in a pH range between 3 and 7, at temperatures between -5.degree. and +30.degree. C.
If a hydroxy group is present in the o-position relative to the azo bridges in the radicals of the diazo components, that is to say if R.sub.1 =OH, the dyestuffs are converted to the heavy metal complex dyestuffs by adding a heavy metal donor to the dyestuff solution or the dyestuff suspension, if necessary with an acid-binding agent and if necessary by treatment at elevated temperature (in general the reaction can be carried out at 0.degree.-120.degree. C.) until the conversion to the desired heavy metal complex dyestuff is complete.
Examples of heavy metal donors which can be used are: copper salts, such as copper sulfate, copper chloride, copper acetate or copper carbonate, chromium salts, such as chromium formate, chromium acetate, chromium sulfate, potash/chrome alum or chromium/salicylic acid, or cobalt salts, such as cobalt sulfate, cobalt chloride or a cobalt/tartaric acid complex.
Acid-binding agents used when converting the dyestuffs to the heavy metal complex dyestuffs are preferably alkali metal salts of weak inorganic or organic acids, such as sodium carbonate, sodium bicarbonate or sodium acetate.
If R.sub.1 is an alkoxy group, preferably a methoxy group, this can be converted by known methods, during the reaction to convert the dyestuff to the heavy metal complex dyestuff, preferably the copper complex dyestuff, to a hydroxy group and the latter can participate in the formation of the complex.
If R.sub.1 is a hydrogen atom, this can be replaced by a hydroxy group under the conditions of oxidative coppering [Angew. Chem. 70, 232-238 (1958)], with simultaneous incorporation of the said hydroxy group into the complex compound. The oxidizing agents used are advantageously derivatives of hydrogen peroxide, such as sodium peroxide, salts of peroxysulfuric acid or salts of perboric acid, but preferably hydrogen peroxide itself. Advantageous reaction conditions in general lie at 20.degree.-100.degree. C. and at pH values between 7 and 3.
The resulting dyestuffs of the formula (1) or their heavy metal complex compounds are separated off by generally known methods, either by precipitating from the reaction medium by means of electrolytes, such as, for example, sodium chloride or potassium chloride, or by evaporating the reaction solution, for example by spray-drying. If the latter method of isolating the dyestuff is chosen, it is advisable, before evaporating, to remove any amounts of sulfate which may be present in the solutions by precipitating these as gypsum and separating them off by filtration. In some cases, it can also be desirable to supply the dyestuff solution direct, if appropriate after adding buffer substances, as a liquid preparation for use in dyeing.
The present invention also relates to the dyeing and printing of cellulose and polyamide fiber materials with the dyestuffs according to the invention.
Cellulose fiber materials are understood as meaning preferably cotton and regenerated cellulose, but also other vegetable fibers, such as linen, hemp and jute. Polyamide fibers are to be understood as meaning both those of natural origin and those of synthetic origin, that is to say both wool and other animal hairs and silk and also polyamide 6,6, polyamide 6, polyamide 11 or polyamide 4.
The dyestuffs according to the invention can be applied to the said substrates by the application techniques known for reactive dyestuffs.
Thus, with these dyestuffs very good color yields are obtained on cellulose fibers by the exhaustion method from a long liquor, using very diverse alkali additives.
Excellent color yields are also obtained on cellulose fibers by the pad method, and the dyes can be fixed by a residence time at room temperature, by steaming or with dry heat.
Intense prints with outlines in a good state and a clear white ground are also obtained by the conventional printing processes for cellulose fibers--in a single phase in the presence of sodium bicarbonate or other acid-binding agents in the printing paste with subsequent steaming at 101.degree.-103.degree. C. or in two phases, printing with a neutral or weakly acid printing paste and then either passing through a hot electrolyte-containing alkaline bath or over-padding with an alkaline electrolyte-containing padding liquor and then developing by means of a residence time, steaming or dry heat. The appearance of the prints is only slightly dependent on changing fixing conditions. Both in dyeing and in printing, the degrees of fixation obtained with the dyestuffs according to the invention are exceptionally high.
With regard to the coloristic properties of the dyestuffs according to the invention, it must be emphasized in particular that these dyestuffs are distinguished by good stability in printing pastes and padding liquors, including in the presence of alkali, by a very good uptake from a long liquor, by good color build-up by the conventional dyeing and printing processes, by an identical depth of shade when dyeing on cotton and regenerated cellulose fibers, by levelness of the dyeings and prints produced therewith and also by a uniform appearance of the dyeings from a long liquor on the addition of various amounts of electrolytes, such as sodium sulfate or sodium chloride.
The fastness properties of the dyeings and prints obtained with the aid of the dyestuffs according to the invention, especially those on cellulose fibers, are appreciable. This equally applies in the case of the most important fastnesses to manufacturing processes and fastness properties in use. The fastness to light, the fastness to wet processing, such as fastness to washing, fastness to milling, fastness to water and fastness to seawater, and the fastness to ironing and fastness to rubbing should be mentioned in particular.
The dyeings on polyamide fibers are usually carried out from an acid medium. Thus, for example, acetic acid or acetic acid and ammonium acetate can be added to the dyebath in order to obtain the desired pH value. In order to obtain a usable levelness of the dyeings, it is advisable to add conventional levelling agents, for example those based on a reaction product of cyanuric chloride with three times the molar amount of an aminobenzenesulfonic acid and/or of an aminonaphthalenesulfonic acid and/or those based on a reaction product of, for example, stearylamine with ethylene oxide. The dyeings can be carried out either at the boil or at 110.degree. to 120.degree. C.

The examples which follow serve to illustrate the invention. The relationship between parts by weight and parts by volume is the same as that between kilogram and liter. The percentages are by weight unless stated otherwise.
EXAMPLE 1
(a) 18.5 parts by weight of cyanuric chloride are dissolved in 60 parts by volume of acetone and the solution is then allowed to run into 500 parts by volume of cold water, with stirring. A solution of 31.9 parts by weight of 1-amino-8-naphthol-3,6-disulfonic acid in 150 parts by volume of water, which has been neutralized with 12 parts by weight of aqueous 33% sodium hydroxide solution, is added immediately to the suspension thus obtained and the resulting mixture is stirred for 15 minutes. A neutral solution of 20.7 parts by weight of the disodium salt of 4,4'-diaminostilbene-2,2'-disulfonic acid in 250 parts by volume of water is then added, immediately thereafter 30 parts by weight of crystalline sodium acetate are introduced and the mixture is then stirred for several hours. The diazonium salt solution obtained in the following way is then added to the reaction mixture thus obtained:
28.1 parts by weight of aniline-4-.beta.-sulfatoethylsulfone are dissolved in 140 parts by volume of water and 60 parts by weight of ice with the addition of about 6.5 parts by weight of calcined sodium carbonate to give a neutral solution, 20.5 parts by volume of aqueous 5 N sodium nitrite solution are then added and the solution thus obtained is allowed to run into a mixture of 25 parts by volume of aqueous 31% hydrochloric acid and 150 parts by weight of ice. The mixture is stirred for 1 hour at 0.degree.-5.degree. C., excess nitrous acid is then destroyed with a little amidosulfonic acid and the pH is then adjusted to 5.5-6.0 with 4 parts by weight of sodium bicarbonate. The reaction mixture described initially is added to this diazonium salt solution and the coupling reaction is carried out at 10.degree.-12.degree. C. and pH 5.5-6.0 for 15 hours. The coupling mixture is then warmed to 60.degree. C. and, after adding 5 parts by weight of kieselguhr, is clarified. The dyestuff is precipitated from the filtrate by introducing 25%-based on the volume--of sodium chloride and is filtered off, dried in vacuo at 60.degree. C. and ground.
This gives 253 parts by weight of a brown dyestuff powder, with which red dyeings of good general fastness properties can be produced on cellulose materials in the presence of alkaline agents.
The dyestuff has the following constitution: ##STR101##
(b) The dyestuff with virtually the same properties can be obtained when 2 moles of the dyestuff of the formula ##STR102## described in Japanese Published Patent Sho 38-23,287, are reacted with one mole of 4,4'-diaminostilbene-2,2'-disulfonic acid at a somewhat higher temperature and a pH of 6.5-7.0 in an aqueous medium.
(c) Furthermore, the dyestuff can be prepared when 2 moles of the aminoazo dyestuff of the formula ##STR103## which can be obtained by coupling diazotized aniline-4-.beta.-hydroxyethylsulfone with 1-acetylamino-8-naphthol-3,6-disulfonic acid, saponifying the acetylamino group to the free amino group and esterifying the .beta.-hydroxyethylsulfonyl group by means of an excess of 100% strength sulfuric acid to the .beta.-sulfatoethylsulfonyl group, are reacted with 1 mole of the compound of the formula ##STR104## which can be prepared in a known manner by reacting a solution of 1 mole of the disodium salt of 4,4'-diaminostilbene-2,2'-disulfonic acid in approximately 15 times the amount by weight of water with a solution of 2 moles of cyanuric chloride in acetone at 0.degree. C., with the addition of a solution of barely 2 moles of sodium carbonate in 5 times the amount by weight of water, in an aqueous medium at elevated temperature, a pH value of 6.9-7.2 being maintained.
EXAMPLE 2
If a neutral solution of 22.4 parts by weight of the disodium salt of 4,4'-diamino-3,3'-dimethoxy-diphenyl-6,6'-disulfonic acid in 300 parts by volume of water is employed in place of the solution of 20.7 parts by weight of the disodium salt of 4,4'-diaminostilbene-2,2'-disulfonic acid in Example 1 and in other respects the procedure is as described in Example 1, this gives, when the dyestuff is precipitated with 20%, based on the volume, of potassium chloride, filtered off, dried in vacuo at 60.degree. C. and ground, 169 parts by weight of a brown powder with which red dyeings and prints of good general fastness properties can be produced on cellulose materials in the presence of acid-binding agents.
The dyestuff has the following constitution: ##STR105##
Dyestuffs can be obtained in a manner analogous to that described in Examples 1 and 2 from the diazo components and coupling components listed in the table which follows; these dyestuffs dye and print cotton in the indicated color shades.
TABLE 1__________________________________________________________________________Example Color shadeNo. Diazo component Coupling component on cotton__________________________________________________________________________3 2 moles of aniline-3-.beta.- condensation product of 2 moles of red sulfatoethylsulfone primary condensation product obtained from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid4 2 moles of 2-aminoanisole-5- condensation product of 2 moles of claret .beta.-sulfatoethylsulfone primary condensation product obtained from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid5 2 moles of 2-aminoanisole-4- condensation product of 2 moles of claret .beta.-sulfatoethylsulfone primary condensation product obtained from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid6 2 moles of 2-aminotoluene-4- condensation product of 2 moles of red .beta.-sulfatoethylsulfone primary condensation product obtained from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid7 2 moles of 2-methoxy-5-methyl- condensation product of 2 moles of claret aniline-4-.beta.-sulfatoethyl- primary condensation product obtained sulfone from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid8 2 moles of 2,5-dimethoxy- condensation product of 2 moles of claret aniline-4-.beta.-sulfatoethylsulfone primary condensation product obtained from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid9 2 moles of 2-chloroaniline-5- condensation product of 2 moles of red .beta.-sulfatoethylsulfone primary condensation product obtained from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid10 2 moles of 2,6-dimethylaniline- condensation product of 2 moles of red 4-.beta.-sulfatoethylsulfone primary condensation product obtained from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid11 2 moles of 2,6-dimethylaniline- condensation product of 2 moles of red 3-.beta.-sulfatoethylsulfone primary condensation product obtained from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid12 2 moles of 2,4-dimethoxyaniline- condensation product of 2 moles of bluish-tinged red 5-.beta.-sulfatoethylsulfone primary condensation product obtained from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid13 2 moles of 2-aminoanisole-4-.beta.- condensation product of 2 moles of claret thiosulfatoethylsulfone primary condensation product obtained from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid14 2 moles of aniline-4-.beta.- condensation product of 2 moles of red thiosulfatoethylsulfone primary condensation product obtained from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid15 2 moles of 4-aminoanisole-2- condensation product of 2 moles of claret .beta.-sulfatoethylsulfone primary condensation product obtained from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid16 2 moles of 4-.beta.-sulfatoethyl- condensation product of 2 moles of red sulfonylaniline-2-sulfonic primary condensation product obtained acid from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid17 2 moles of 4-aminotoluene-2- condensation product of 2 moles of red .beta.-sulfatoethylsulfone primary condensation product obtained from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid18 2 moles of 2-aminoanisole- condensation product of 2 moles of claret 4-vinylsulfone primary condensation product obtained from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid19 2 moles of aniline-4-vinyl- condensation product of 2 moles of red sulfone primary condensation product obtained from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid20 2 moles of aniline-3-vinyl- condensation product of 2 moles of red sulfone primary condensation product obtained from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid21 2 moles of 2-bromoaniline-4-.beta.- condensation product of 2 moles of red sulfatoethylsulfone primary condensation product obtained from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid22 2 moles of 2,6-dichloroaniline- condensation product of 2 moles of red 4-.beta.-sulfatoethylsulfone primary condensation product obtained from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid23 2 moles of 6-.beta.-sulfatoethyl- condensation product of 2 moles of bluish-tinged sulfonyl-2-aminonaphthalene- primary condensation product redained 1-sulfonic acid from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid24 2 moles of 2-naphthylamine-5- condensation product of 2 moles of red .beta.-sulfatoethylsulfone primary condensation product obtained from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid25 2 moles of 2-naphthylamine-8- condensation product of 2 moles of bluish-tinged .beta.-sulfatoethylsulfone primary condensation product redained from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid26 2 moles of 2-naphthylamine-6- condensation product of 2 moles of bluish-tinged .beta.-sulfatoethylsulfone primary condensation product redained from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid27 2 moles of 2-chloroaniline- condensation product of 2 moles of red 4-.beta.-sulfatoethylsulfone primary condensation product obtained from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid28 2 moles of 2-amino-4-.beta.- condensation product of 2 moles of red sulfatoethylsulfonyl- primary condensation product obtained benzoic acid from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid29 2 moles of 5-.beta.-sulfatoethyl- condensation product of 2 moles of red sulfonylaniline-2-sulfonic acid primary condensation product obtained from cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid in an equimolar ratio with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid30 2 moles of aniline-4-.beta.- condensation product of 2 moles of red sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-naphthol-4,6- disulfonic acid with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid31 2 moles of aniline-3-.beta.- condensation product of 2 moles of red sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-naphthol-4,6- disulfonic acid with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid32 2 moles of aniline-4-.beta.- condensation product of 2 moles of red thiosulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-naphthol-4,6- disulfonic acid with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid33 2 moles of aniline-4-vinyl- condensation product of 2 moles of red sulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-naphthol-4,6- disulfonic acid with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid34 2 moles of 2-aminoanisole-4- condensation product of 2 moles of claret .beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-naphthol-4,6- disulfonic acid with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid35 2 moles of 2-methoxy-5-methyl- condensation product of 2 moles of claret aniline-4-.beta.-sulfatoethyl- primary condensation product obtained sulfone from equimolar amounts of cyanuric chloride and 1-amino-8-naphthol-4,6- disulfonic acid with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid36 2 moles of 2,5-dimethoxy- condensation product of 2 moles of claret aniline-4-.beta.-sulfatoethyl- primary condensation product obtained sulfone from equimolar amounts of cyanuric chloride and 1-amino-8-naphthol-4,6- disulfonic acid with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid37 2 moles of 8-.beta.-sulfatoethyl- condensation product of 2 moles of claret sulfonyl-2-amino-naphthalene- primary condensation product obtained 6-sulfonic acid from equimolar amounts of cyanuric chloride and 1-amino-8-naphthol-4,6- disulfonic acid with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid38 2 moles of 6-.beta.-sulfatoethyl- condensation product of 2 moles of bluish-tinged sulfonyl-2-amino-naphthalene- primary condensation product redained 1-sulfonic acid from equimolar amounts of cyanuric chloride and 1-amino-8-naphthol-4,6- disulfonic acid with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid39 2 moles of 2-naphthylamine-6- condensation product of 2 moles of bluish-tinged .beta.-sulfatoethylsulfone primary condensation product redained from equimolar amounts of cyanuric chloride and 1-amino-8-naphthol-4,6- disulfonic acid with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid40 2 moles of 2-naphthylamine-8- condensation product of 2 moles of bluish-tinged .beta.-sulfatoethylsulfone primary condensation product redained from equimolar amounts of cyanuric chloride and 1-amino-8-naphthol-4,6- disulfonic acid with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid41 2 moles of 2-naphthylamine-5- condensation product of 2 moles of red .beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-naphthol-4,6- disulfonic acid with 1 mole of 4,4'- diaminostilbene-2,2'-disulfonic acid42 2 moles of aniline-4-.beta.- condensation product of 2 moles of red sulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-naphthol-6-sulfonic acid with 1 mole of 4,4'-diaminostilbene- 2,2'-disulfonic acid43 2 moles of aniline-3-.beta. condensation product of 2 moles of orange sulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-naphthol-6-sulfonic acid with 1 mole of 4,4'-diaminostilbene- 2,2'-disulfonic acid44 2 moles of aniline-4-vinyl- condensation product of 2 moles of orange sulfone condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-naphthol-6-sulfonic acid with 1 mole of 4,4'-diaminostilbene- 2,2'-disulfonic acid45 2 moles of aniline-4-.beta.-thio- condensation product of 2 moles of orange sulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-napthol-6-sulfonic acid with 1 mole of 4,4'-diaminostilbene- 2,2'-disulfonic acid46 2 moles of 2-aminoanisole-4-.beta.- condensation product of 2 moles of red sulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-naphthol-6-sulfonic acid with 1 mole of 4,4'-diaminostilbene- 2,2'-disulfonic acid47 2 moles of aniline-3-vinyl- condensation product of 2 moles of orange sulfone condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-naphthol-6-sulfonic acid with 1 mole of 4,4'-diaminostilbene- 2,2'-disulfonic acid48 2 moles of 2-aminoanisole-4- condensation product of 2 moles of red .beta.-thiosulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-naphthol-6-sulfonic acid with 1 mole of 4,4'-diaminostilbene- 2,2'-disulfonic acid49 2 moles of 2,5-dimethoxyaniline- condensation product of 2 moles of bluish-tinged 4-.beta.-sulfatoethylsulfone condensation product obtained redm equimolar amounts of cyanuric chloride and 2-amino-8-naphthol-6-sulfonic acid with 1 mole of 4,4'-diaminostilbene- 2,2'-disulfonic acid50 2 moles of 2-methoxy-5-methyl- condensation product of 2 moles of red aniline-4-.beta.-sulfatoethyl- condensation product obtained from sulfone equimolar amounts of cyanuric chloride and 2-amino-8-naphthol-6-sulfonic acid with 1 mole of 4,4'-diaminostilbene- 2,2'-disulfonic acid51 2 moles of 2-aminonaphthalene- condensation product of 2 moles of red 8-.beta.-sulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-naphthol-6-sulfonic acid with 1 mole of 4,4'-diaminostilbene- 2,2'-disulfonic acid52 2 moles of 2-aminonaphthalene- condensation product of 2 moles of red 6-.beta.-sulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-naphthol-6-sulfonic acid with 1 mole of 4,4'-diaminostilbene- 2,2'-disulfonic acid53 2 moles of 2-aminonaphthalene- condensation product of 2 moles of red 5-.beta.-sulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-naphthol-6-sulfonic acid with 1 mole of 4,4'-diaminostilbene- 2,2'-disulfonic acid54 2 moles of aniline-4-.beta.- condensation product of 2 moles of orange sulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-5-naphthol-7-sulfonic acid with 1 mole of 4,4'-diaminostilbene- 2,2'-disulfonic acid55 2 moles of aniline-4-.beta.-thio- condensation product of 2 moles of orange sulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-5-naphthol-7-sulfonic acid with 1 mole of 4,4'-diaminostilbene- 2,2'-disulfonic acid56 2 moles of aniline-3-vinyl- condensation product of 2 moles of orange sulfone condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-5-naphthol-7-sulfonic acid with 1 mole of 4,4'-diaminostilbene- 2,2'-disulfonic acid57 2 moles of aniline-3-.beta.- condensation product of 2 moles of orange sulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-5-naphthol-7-sulfonic acid with 1 mole of 4,4'-diaminostilbene- 2,2'-disulfonic acid58 2 moles of 2-aminoanisole-4- condensation product of 2 moles of reddish- .beta.-sulfatoethylsulfone condensation product obtained tinged orange equimolar amounts of cyanuric chloride and 2-amino-5-naphthol-7-sulfonic acid with 1 mole of 4,4'-diaminostilbene- 2,2'-disulfonic acid59 2 moles of 2-aminoanisole-4- condensation product of 2 moles of reddish- .beta.-thiosulfatoethylsulfone condensation product obtained tinged orange equimolar amounts of cyanuric chloride and 2-amino-5-naphthol-7-sulfonic acid with 1 mole of 4,4'-diaminostilbene- 2,2'-disulfonic acid60 2 moles of 2-aminoanisole-5- condensation product of 2 moles of red .beta.-sulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-5-naphthol-7-sulfonic acid with 1 mole of 4,4'-diaminostilbene- 2,2'-disulfonic acid61 2 moles of 2-methoxy-5-methyl- condensation product of 2 moles of red aniline-4-.beta.-sulfatoethyl- condensation product obtained from sulfone equimolar amounts of cyanuric chloride and 2-amino-5-naphthol-7-sulfonic acid with 1 mole of 4,4'-diaminostilbene- 2,2'-disulfonic acid62 2 moles of 2,5-dimethoxyaniline- condensation product of 2 moles of red 4-.beta.-sulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-5-naphthol-7-sulfonic acid with 1 mole of 4,4'-diaminostilbene- 2,2'-disulfonic acid63 2 moles of 2-aminonaphthalene- condensation product of 2 moles of reddish- 8-.beta.-sulfatoethylsulfone condensation product obtained tinged orange equimolar amounts of cyanuric chloride and 2-amino-5-naphthol-7-sulfonic acid with 1 mole of 4,4'-diaminostilbene- 2,2'-disulfonic acid64 2 moles of 8-.beta.-sulfatoethyl- condensation product of 2 moles of reddish- sulfonyl-2-amino-naphthalene- condensation product obtained tinged orange 6-sulfonic acid equimolar amounts of cyanuric chloride and 2-amino-5-naphthol-7-sulfonic acid with 1 mole of 4,4'-diaminostilbene- 2,2'-disulfonic acid65 2 moles of 6-.beta.-sulfatoethyl- condensation product of 2 moles of orange sulfonyl-2-amino-naphthalene- condensation product obtained from 1-sulfonic acid equimolar amounts of cyanuric chloride and 2-amino-5-naphthol-7-sulfonic acid with 1 mole of 4,4'-diaminostilbene- 2,2'-disulfonic acid66 2 moles of aniline-4-.beta.- condensation product of 2 moles of red sulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric bromide and 1-amino-8-naphthol-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid67 2 moles of aniline-3-.beta.- condensation product of 2 moles of red sulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric bromide and 1-amino-8-naphthol-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid68 2 moles of aniline-4-.beta.- condensation product of 2 moles of red thiosulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric bromide and 1-amino-8-naphthol-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid69 2 moles of aniline-3-vinyl- condensation product of 2 moles of red sulfone condensation product obtained from equimolar amounts of cyanuric bromide and 1 amino-8-naphthol-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid70 2 moles of 2-aminoanisole-4- condensation product of 2 moles of claret .beta.-sulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric bromide and 1-amino-8-naphthol-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2' -disulfonic acid71 2 moles of 2-aminoanisole-4-.beta.- condensation product of 2 moles of claret thiosulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric bromide and 1-amino-8-naphthol-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid72 2 moles of 2-aminoanisole-5-.beta.- condensation product of 2 moles of bluish-tinged sulfatoethylsulfone condensation product obtained redm equimolar amounts of cyanuric bromide and 1-amino-8-naphthol-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid73 2 moles of 2,5-dimethoxy- condensation product of 2 moles of claret aniline-4-.beta.-sulfatoethyl- condensation product obtained from sulfone equimolar amounts of cyanuric bromide and 1-amino-8-naphthol-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid74 2 moles of 2-methoxy-5-methyl- condensation product of 2 moles of claret aniline-4-.beta.-sulfatoethyl condensation product obtained from sulfone equimolar amounts of cyanuric bromide and 1-amino-8-naphthol-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid75 2 moles of 8-.beta.-sulfatoethyl- condensation product of 2 moles of claret sulfonyl-2-aminonaphthalene- condensation product obtained from 6-sulfonic acid equimolar amounts of cyanuric bromide and 1-amino-8-naphthol-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid76 2 moles of 6-.beta.-sulfatoethyl- condensation product of 2 moles of bluish-tinged sulfonyl-2-aminonaphthalene- condensation product obtained redm 1-sulfonic acid equimolar amounts of cyanuric bromide and 1-amino-8-naphthol-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid77 2 moles of aniline-4-.beta.- condensation product of 2 moles of red sulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric fluoride and 1-amino-8-naphthol-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid78 2 moles of aniline-3-.beta.- condensation product of 2 moles of red sulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric fluoride and 1-amino-8-naphthol-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid79 2 moles of 2-aminoanisole-4- condensation product of 2 moles of claret .beta.-sulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric fluoride and 1-amino-8-naphthol-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid80 2 moles of aniline-4-.beta.-thio- condensation product of 2 moles of red sulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric fluoride and 1-amino-8-naphthol-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid81 2 moles of aniline-4-vinyl- condensation product of 2 moles of red sulfone condensation product obtained from equimolar amounts of cyanuric fluoride and 1-amino-8-naphthol-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid82 2 moles of aniline-3-vinyl- condensation product of 2 moles of red sulfone condensation product obtained from equimolar amounts of cyanuric fluoride and 1-amino-8-naphthol-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid83 2 moles of 2-aminoanisole-4- condensation product of 2 moles of claret .beta.-thiosulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-naphthol-3,6-disulfonic acid with 1 mole of 3,3'-dimethoxy- benzidine-6,6'-disulfonic acid84 2 moles of 2,5-dimethoxyaniline- condensation product of 2 moles of claret 4-.beta.-sulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-naphthol-3,6-disulfonic acid with 1 mole of 3,3'-dimethoxy- benzidine-6,6'-disulfonic acid85 2 moles of 2-methoxy-5-methyl- condensation product of 2 moles of claret aniline-4-.beta.-sulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-naphthol-3,6-disulfonic acid with 1 mole of 3,3'-dimethoxy- benzidine-6,6'-disulfonic acid86 2 moles of 8-.beta.-sulfatoethyl- condensation product of 2 moles of claret sulfonyl-2-amino-naphthalene- condensation product obtained from 6-sulfonic acid equimolar amounts of cyanuric chloride and 1-amino-8-naphthol-3,6-disulfonic acid with 1 mole of 3,3'-dimethoxy- benzidine-6,6'-disulfonic acid87 2 moles of 6-.beta.-sulfatoethyl- condensation product of 2 moles of bluish-tinged sulfonyl-2-amino-naphthalene- condensation product obtained redm 1-sulfonic acid equimolar amounts of cyanuric chloride and 1-amino-8-naphthol-3,6-disulfonic acid with 1 mole of 3,3'-dimethoxy- benzidine-6,6'-disulfonic acid88 2 moles of aniline-4-.beta.- condensation product of 2 moles of red sulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-naphthol-3,6-disulfonic acid with 1 mole of 3,3'-dimethoxy- benzidine-6,6'-disulfonic acid89 2 moles of aniline-4-.beta.-thio- condensation product of 2 moles of red sulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-naphthol-3,6-disulfonic acid with 1 mole of 3,3'-dimethoxy- benzidine-6,6'-disulfonic acid90 2 moles of aniline-3-.beta.- condensation product of 2 moles of red sulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-naphthol-3,6-disulfonic acid with 1 mole of 3,3'-dimethoxy- benzidine-6,6'-disulfonic acid91 2 moles of 2-aminoanisole-4- condensation product of 2 moles of orange .beta.-sulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-naphthol-6-sulfonic acid with 1 mole of 3,3'-dimethoxy-6,6'- disulfonic acid92 2 moles of 2-methoxy-5-methyl- condensation product of 2 moles of red aniline-4-.beta.-sulfatoethyl- condensation product obtained from sulfone equimolar amounts of cyanuric chloride and 2-amino-8-naphthol-6-sulfonic acid with 1 mole of 3,3'-dimethoxy-6,6'- disulfonic acid93 2 moles of aniline-4-.beta.-sulfato- condensation product of 2 moles of orange ethylsulfone condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-naphthol-6-sulfonic acid with 1 mole of 3,3'-dimethoxy-6,6'- disulfonic acid94 2 moles of 8-.beta.-sulfatoethyl- condensation product of 2 moles of red sulfonyl-2-amino-naphthalene- condensation product obtained from 6-sulfonic acid equimolar amounts of cyanuric chloride and 2-amino-8-naphthol-6-sulfonic acid with 1 mole of 3,3'-dimethoxy-6,6'- disulfonic acid95 2 moles of 6-.beta.-sulfatoethyl- condensation product of 2 moles of red sulfonyl-2-amino-naphthalene condensation product obtained from 1-sulfonic acid equimolar amounts of cyanuric chloride and 2-amino-8-naphthol-6-sulfonic acid with 1 mole of 3,3'-dimethoxy-6,6'- disulfonic acid96 2 moles of 2,5-dimethoxyaniline- condensation product of 2 moles of bluish-tinged 4-.beta.-sulfatoethylsulfone condensation product obtained redm equimolar amounts of cyanuric chloride and 2-amino-8-naphthol-6-sulfonic acid with 1 mole of 3,3'-dimethoxy-6,6'- disulfonic acid97 2 moles of aniline-4-.beta.-sulfato- condensation product of 2 moles of the orange ethylsulfone condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-5-naphthol-7-sulfonic acid with 1 mole of 3,3'-dimethoxy- benzidine-6,6'-disulfonic acid98 2 moles of 2-aminoanisole-4- condensation product of 2 moles of reddish- .beta.-thiosulfatoethylsulfone condensation product obtained tinged orange equimolar amounts of cyanuric chloride with 1 mole of 3,3'-dimethoxy- benzidine-6,6'-disulfonic acid99 2 moles of aniline-3-vinyl- condensation product of 2 moles of orange sulfone condensation product obtained from equimolar amounts of cyanuric and 2-amino-5-naphthol-7-s ulfonic acid with 1 mole of 3,3'-dimethoxy- benzidine-6,6'-disulfonic acid100 2 moles of 2,6-dimethylaniline- condensation product of 2 moles of the orange 4-.beta.-sulfatoethylsulfone condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-5-naphthol-7-sulfonic acid with 1 mole of 3,3'dimethoxy- benzidine-6,6'-disulfonic acid101 2 moles of aniline-4-.beta.-sulfato- reaction product of 2 moles of red ethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,1-bis-(4'-aminophenyl)- cyclohexane102 2 moles of aniline-4-.beta.-chloro- reaction product of 2 moles of red ethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,1-bis-(4'-aminophenyl)- cyclohexane103 2 moles of aniline-3-.beta.-sulfato- reaction product of 2 moles of red ethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,1-bis-(4'-aminophenyl)- cyclohexane104 2 moles of 2-aminoanisole-5- reaction product of 2 moles of claret .beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,1-bis-(4'-aminophenyl)- cyclohexane105 2 moles of 2-aminoanisole-4- reaction product of 2 moles of claret .beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,1-bis-(4'-aminophenyl)- cyclohexane106 2 moles of 2-aminotoluene-4- reaction product of 2 moles of red .beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,1-bis-(4'-aminophenyl)- cyclohexane107 2 moles of 2-methoxy-5-methyl- reaction product of 2 moles of claret aniline-4-.beta.-sulfatoethyl- primary condensation product obtained sulfone from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,1-bis-(4'-aminophenyl)- cyclohexane108 2 moles of 2,5-dimethoxy- reaction product of 2 moles of claret aniline-4-.beta.-sulfatoethyl- primary condensation product obtained sulfone from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,1-bis-(4'-aminophenyl)- cyclohexane109 2 moles of 2-chloroaniline-5- reaction product of 2 moles of red .beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,1-bis-(4'-aminophenyl)- cyclohexane110 2 moles of 2,6-dimethylaniline- reaction product of 2 moles of red 4-.beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,1-bis-(4'-aminophenyl)- cyclohexane111 2 moles of 2,6-dimethylaniline- reaction product of 2 moles of red 3-.beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,1-bis-(4'-aminophenyl)- cyclohexane112 2 moles of 2,4-dimethoxy- reaction product of 2 moles of bluish-tinged aniline-5-.beta.-sulfatoethyl- primary condensation product redained sulfone from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,1-bis-(4'-aminophenyl)- cyclohexane113 2 moles of 2-aminoanisole-4- reaction product of 2 moles of claret .beta.-thiosulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,1-bis-(4'-aminophenyl)- cyclohexane114 2 moles of aniline-4-.beta.-thio- reaction product of 2 moles of red sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,1-bis-(4'-aminophenyl)- cyclohexane115 2 moles of 4-aminoanisole-2- reaction product of 2 moles of red .beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphhthalene-3,6-disulfonic acid with 1 mole of 1,1-bis-(4'-aminophenyl)- cyclohexane116 2 moles of 4-.beta.-sulfatoethyl- reaction product of 2 moles of red sulfonylaniline-2-sulfonic primary condensation product obtained acid from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,1-bis-(4'-aminophenyl)- cyclohexane117 2 moles of 4-aminotoluene-2- reaction product of 2 moles of orange .beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-6-sulfonic acid with 1 mole of 1,1-bis-(4'-amino-3'-sulfophenyl)- cyclohexane118 2 moles of 2-aminoanisole-4- reaction product of 2 moles of yellowish- vinylsulfone primary condensation product tinged red from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-6-sulfonic acid with 1 mole of 1,1-bis-(4'-amino-3'-sulfo- phenyl)-cyclohexane119 2 moles of aniline-4-vinyl reaction product of 2 moles of orange sulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-6-sulfonic acid with 1 mole of 1,1-bis-(4'-amino-3'-sulfo- phenyl)-cyclohexane120 2 moles of aniline-3-vinyl- reaction product of 2 moles of orange sulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-6-sulfonic acid with 1 mole of 1,1-bis-(4'-amino-3'-sulfo- phenyl)-cyclohexane121 2 moles of 2-bromoaniline-4- reaction product of 2 moles of orange .beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxy- naphhthalene-6-sulfonic acid with 1 mole of 1,1-bis-(4'-amino-3'-sulfo- phenyl)-cyclohexane122 2 moles of 2,6-dichloroaniline- reaction product of 2 moles of orange 4-.beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-6-sulfonic acid with 1 mole of 1,1-bis-(4'-amino-3'-sulfo- phenyl)-cyclohexane123 2 moles of 6-.beta.-sulfatoethyl- reaction product of 2 moles of yellowish- sulfonyl-2-amino-naphthalene- primary condensation product tinged red 1-sulfonic acid from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-6-sulfonic acid with 1 mole of 1,1-bis-(4'-amino-3'-sulfo- phenyl)-cyclohexane124 2 moles of 2-naphthylamine-5- reaction product of 2 moles of orange .beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-6-sulfonic acid with 1 mole of 1,1-bis-(4'-amino-3'-sulfo- phenyl)-cyclohexane125 2 moles of 2-naphthylamine-8- reaction product of 2 moles of yellowish- .beta.-sulfatoethylsulfone primary condensation product tinged red from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-6-sulfonic acid with 1 mole of 1,1-bis-(4'-amino-3'-sulfo- phenyl)-cyclohexane126 2 moles of 2-naphthylamine-6- reaction product of 2 moles of yellowish- .beta.-sulfatoethylsulfone primary condensation product tinged red from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-6-sulfonic acid with 1 mole of 1,1-bis-(4'-amino-3'-sulfo- phenyl)-cyclohexane127 2 moles of 2-chloroaniline-4- reaction product of 2 moles of orange .beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-6-sulfonic acid with 1 mole of 1,1-bis-(4'-amino-3' -sulfo- phenyl)-cyclohexane128 2 moles of 2-amino-4-.beta.- reaction product of 2 moles of orange sulfatoethylsulfonyl- primary condensation product obtained benzoic acid from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-6-sulfonic acid with 1 mole of 1,1-bis-(4'-amino-3'-sulfo- phenyl)-cyclohexane129 2 moles of 5-.beta.-sulfatoethyl- reaction product of 2 moles of orange sulfonyl-aniline-2-sulfonic primary condensation product obtained acid from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-6-sulfonic acid with 1 mole of 1,1-bis-(4'-amino-3'-sulfo- phenyl)-cyclohexane130 2 moles of aniline-4-.beta.- reaction product of 2 moles of orange sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-5-hydroxy- naphthalene-7-sulfonic acid with 1 mole of 4,4'-diaminodiphenylamine-2- sulfonic acid131 2 moles of aniline-3-.beta.- reaction product of 2 moles of orange sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-5-hydroxy- naphthalene-7-sulfonic acid with 1 mole of 4,4'-diaminodiphenylamine-2- sulfonic acid132 2 moles of aniline-4-.beta.-thio- reaction product of 2 moles of orange sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-5-hydroxy- naphthalene-7-sulfonic acid with 1 mole of 4,4'diaminodiphenylamine-2- sulfonic acid133 2 moles of aniline-4-vinyl- reaction product of 2 moles of orange sulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-5-hydroxy- naphthalene-7-sulfonic acid with 1 mole of 4,4'-diaminodiphenylamine-2- sulfonic acid134 2 moles of 2-aminoanisole-4- reaction product of 2 moles of bluish-tinged .beta.-sulfatoethylsulfone primary condensation product of redi- molar amounts of cyanuric chloride and 1-amino-8-hydroxynaphthalene- 4,6-disulfonic acid with 1 mole of 1,6-diaminohexane135 2 moles of 2-methoxy-5-methyl- reaction product of 2 moles of bluish-tinged aniline-4-.beta.-sulfatoethylsulfone primary condensation product of redi- molar amounts of cyanuric chloride and 1-amino-8-hydroxynaphthalene- 4,6-disulfonic acid with 1 mole of 1,6-diaminohexane136 2 moles of 2,5-dimethoxyaniline- reaction product of 2 moles of claret 4-.beta.-sulfatoethylsulfone primary condensation product of equi- molar amounts of cyanuric chloride and 1-amino-8-hydroxynaphthalene- 4,6-disulfonic acid with 1 mole of 1,6-diaminohexane137 2 moles of 8-.beta.-sulfatoethyl- reaction product of 2 moles of bluish-tinged sulfonyl-2-amino-naphthalene- primary condensation product of redi- 6-sulfonic acid molar amounts of cyanuric chloride and 1-amino-8-hydroxynaphthalene- 4,6-disulfonic acid with 1 mole of 1,6-diaminohexane138 2 moles of 6-.beta.-sulfatoethyl- reaction product of 2 moles of bluish-tinged sulfonyl-2-amino-naphthalene- primary condensation product of redi- 1-sulfonic acid molar amounts of cyanuric chloride and 1-amino-8-hydroxynaphthalene- 4,6-disulfonic acid with 1 mole of 1,6-diaminohexane139 2 moles of 2-naphthylamine-6- reaction product of 2 moles of bluish-tinged .beta.-sulfatoethylsulfone primary condensation product of redi- molar amounts of cyanuric chloride and 1-amino-8-hydroxynaphthalene- 4,6-disulfonic acid with 1 mole of 1,6-diaminohexane140 2 moles of 2-naphthylamine-8- reaction product of 2 moles of bluish-tinged .beta.-sulfatoethylsulfone primary condensation product of redi- molar amounts of cyanuric chloride and 1-amino-8-hydroxynaphthalene- 4,6-disulfonic acid with 1 mole of 1,6-diaminohexane141 2 moles of 2-naphthylamine-5- reaction product of 2 moles of bluish-tinged .beta.-sulfatoethylsulfone primary condensation product of redi- molar amounts of cyanuric chloride and 1-amino-8-hydroxynaphthalene- 4,6-disulfonic acid with 1 mole of 1,6-diaminohexane142 2 moles of aniline-4-.beta.-sulfato- reaction product of 2 moles of red ethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,4-diaminobutane143 2 moles of aniline-3-.beta.- reaction product of 2 moles of red sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,4-diaminobutane144 2 moles of aniline-4-vinyl- reaction product of 2 moles of red sulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,4-diaminobutane145 2 moles of aniline-4-.beta.-thio- reaction product of 2 moles of red sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,4-diaminobutane146 2 moles of 2-aminoanisole-4- reaction product of 2 moles of bluish-tinged .beta.-sulfatoethylsulfone primary condensation product redained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,4-diaminobutane147 2 moles of aniline-3-vinyl- reaction product of 2 moles of red sulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,4-diaminobutane148 2 moles of 2-aminoanisole-4-.beta.- reaction product of 2 moles of bluish-tinged thiosulfatoethylsulfone primary condensation product redained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,4-diaminobutane149 2 moles of 2,5-dimethoxyaniline- reaction product of 2 moles of claret 4-.beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,4-diaminobutane150 2 moles of 2-methoxy-5-methyl- reaction product of 2 moles of yellowish- aniline-4-.beta.-sulfatoethyl- primary condensation product tinged red sulfone from equimolar amounts of cyanuric chloride and 2-amino-5-hydroxy- naphthalene-1,7-disulfonic acid and 1 mole of 1,2-diaminoethane151 2 moles of 2-aminonaphthalene- reaction product of 2 moles of yellowish- 8-.beta.-sulfatoethylsulfone primary condensation product tinged red from equimolar amounts of cyanuric chloride and 2-amino-5-hydroxy- naphthalene-1,7-disulfonic acid and 1 mole of 1,2-diaminoethane152 2 moles of 2-aminonaphthalene- reaction product of 2 moles of yellowish- 6-.beta.-sulfatoethylsulfone primary condensation product tinged red from equimolar amounts of cyanuric chloride and 2-amino-5-hydroxy- naphthalene-1,7-disulfonic acid and 1 mole of 1,2-diaminoethane153 2 moles of 2-aminonaphthalene- reaction product of 2 moles of yellowish- 5-.beta.-sulfatoethylsulfone primary condensation product tinged red from equimolar amounts of cyanuric chloride and 2-amino-5-hydroxy- naphthalene-1,7-disulfonic acid and 1 mole of 1,2-diaminoethane154 2 moles of aniline-4-.beta.-sulfato- reaction product of 2 moles of red ethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,3-bis-aminomethyl- cyclohexane155 2 moles of aniline-4-.beta.-thio- reaction product of 2 moles of red sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,3-bis-aminomethyl- cyclohexane156 2 moles of aniline-3-vinyl- reaction product of 2 moles of red sulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,3-bis-aminomethyl- cyclohexane157 2 moles of aniline-3-.beta.-sulfato- reaction product of 2 moles of red ethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,3-bis-aminomethyl- cyclohexane158 2 moles of 2-aminoanisole-4-.beta.- reaction product of 2 moles of red sulfatoethylsulfone primary condensation product obtained from equimolar anounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,3-bis-aminomethyl- cyclohexane159 2 moles of 2-aminoanisole-4-.beta. - reaction product of 2 moles of red thiosulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,3-bis-aminomethyl- cyclohexane160 2 moles of 2-aminoanisole-5-.beta.- reaction product of 2 moles of red sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,3-bis-aminomethyl- cyclohexane161 2 moles of 2-methoxy-5-methyl- reaction product of 2 moles of bluish-tinged aniline-4-.beta.-sulfatoethylsulfone primary condensation product redained from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,3-bis-aminomethyl- cyclohexane162 2 moles of 2,5-dimethoxyaniline- reaction product of 2 moles of bluish-tinged 4-.beta.-sulfatoethylsulfone primary condensation product redained from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,3-bis-aminomethyl- cyclohexane163 2 moles of 2-aminonaphthalene- reaction product of 2 moles of red 8-.beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,3-bis-aminomethyl- cyclohexane164 2 moles of 8-.beta.-sulfatoethyl- reaction product of 2 moles of red sulfonyl-2-amino-naphthalene- primary condensation product obtained 6-sulfonic acid from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,3-bis-aminomethyl- cyclohexane165 2 moles of 6-.beta.-sulfatoethyl- reaction product of 2 moles of red sulfonyl-2-amino-naphthalene- primary condensation product obtained 1-sulfonic acid from equimolar anounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,3-bis-aminomethyl- cyclohexane166 2 moles of aniline-4-.beta.-sulfato- reaction product of 2 moles of red ethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-4-sulfonic acid with 1 mole of 3,3'-dimethyl-4,4'-diamino-di- phenyl-6,6'-disulfonic acid167 2 moles of aniline-3-.beta.- reaction product of 2 moles of red sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-4-sulfonic acid with 1 mole of 3,3'-dimethyl-4,4'-diamino-di- phenyl-6,6'-disulfonic acid168 2 moles of aniline-4-.beta.- reaction product of 2 moles of red thiosulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-4-sulfonic acid with 1 mole of 3,3'-dimethyl-4,4'-diamino-di- phenyl-6,6'-disulfonic acid169 2 moles of aniline-3-vinyl- reaction product of 2 moles of red sulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-4-sulfonic acid with 1 mole of 3,3'-dimethyl-4,4'-diamino-di- phenyl-6,6'-disulfonic acid170 2 moles of 2-aminoanisole-4- reaction product of 2 moles of red .beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-4-sulfonic acid with 1 mole of 3,3'-dimethyl-4,4'-diamino-di- phenyl-6,6'-disulfonic acid171 2 moles of 2-aminoanisole-4- reaction product of 2 moles of red .beta.-thiosulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-4-sulfonic acid with 1 mole of 3,3'-dimethyl-4,4'-diamino-di- phenyl-6,6'-disulfonic acid172 2 moles of 2-aminoanisole-5- reaction product of 2 moles of red .beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-4-sulfonic acid with 1 mole of 3,3'-dimethyl-4,4'-diamino-di- phenyl-6,6'-disulfonic acid173 2 moles of 2,5-dimethoxyaniline- reaction product of 2 moles of red 4-.beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-4-sulfonic acid with 1 mole of 3,3'-dimethyl-4,4'-diamino-di- phenyl-6,6'-disulfonic acid174 2 moles of 2-methoxy-5-methyl- reaction product of 2 moles of red aniline-4-.beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-4-sulfonic acid with 1 mole of 3,3'-dimethyl-4,4'-diamino-di- phenyl-6,6'-disulfonic acid175 2 moles of 8-.beta.-sulfatoethyl- reaction product of 2 moles of red sulfonyl-2-aminonaphthalene- primary condensation product obtained 6-sulfonic acid from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-4-sulfonic acid with 1 mole of 3,3'-dimethyl-4,4'-diamino-di- phenyl-6,6'-disulfonic acid176 2 moles of 6-.beta.-sulfatoethyl- reaction product of 2 moles of red sulfonyl-2-aminonaphthalene- primary condensation product obtained 1-sulfonic acid from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-4-sulfonic acid with 1 mole of 3,3'-dimethyl-4,4'-diamino-di- phenyl-6,6'-disulfonic acid177 2 moles of aniline-4-.beta.- reaction product of 2 moles of red sulfatoethylsulfone secondary condensation product obtained from equimolar amounts of cyanuric chloride, 1-amino-8-hydroxynaphthalene- 3,6-disulfonic acid and ammonia with 1 mole of 4,4'-diaminostilbene-2,2'- disulfonic acid178 2 moles of aniline-3-.beta.-sulfato- reaction product of 2 moles of red ethylsulfone secondary condensation product obtained from equimolar amounts of cyanuric chloride, 1-amino-8-hydroxynaphthalene- 3,6-disulfonic acid and ammonia with 1 mole of 4,4'-diaminostilbene-2,2'- disulfonic acid179 2 moles of 2-aminoanisole-4-.beta.- reaction product of 2 moles of bluish-tinged sulfatoethylsulfone secondary condensation product redained from equimolar amounts of cyanuric chloride, 1-amino-8-hydroxynaphthalene- 3,6-disulfonic acid and ammonia with 1 mole of 4,4'-diaminostilbene-2,2'- disulfonic acid180 2 moles of aniline-.beta.-thio- reaction product of 2 moles of red sulfatoethylsulfone secondary condensation product obtained from equimolar amounts of cyanuric chloride, 1-amino-8-hydroxynaphthalene- 3,6-disulfonic acid and ammonia with 1 mole of 4,4'-diaminostilbene-2,2'- disulfonic acid181 2 moles of aniline-4-vinyl- reaction product of 2 moles of red sulfone secondary condensation product obtained from equimolar amounts of cyanuric chloride, 1-amino-8-hydroxynaphthalene- 3,6-disulfonic acid and ammonia with 1 mole of 4,4'-diaminostilbene-2,2'- disulfonic acid182 2 moles of aniline-3-vinyl- reaction product of 2 moles of red sulfone secondary condensation product obtained from equimolar amounts of cyanuric chloride, 1-amino-8-hydroxynaphthalene- 3,6-disulfonic acid and ammonia with 1 mole of 4,4'-diaminostilbene-2,2'- disulfonic acid183 2 moles of 2-aminoanisole-4- reaction product of 2 moles of red .beta.-thiosulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-4,6-disulfonic acid with 1 mole of 1,4-diaminobenzene-3,6- disulfonic acid184 2 moles of 2,5-dimethoxy- reaction product of 2 moles of claret aniline-4-.beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-4,6-disulfonic acid with 1 mole of 1,4-diaminobenzene-3,6- disulfonic acid185 2 moles of 2-methoxy-5-methyl- reaction product of 2 moles of claret aniline-4-.beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-4,6-disulfonic acid with 1 mole of 1,4-diaminobenzene-3,6- disulfonic acid186 2 moles of 8-.beta.-sulfatoethyl- reaction product of 2 moles of bluish-tinged sulfonyl-2-amino-naphthalene- primary condensation product redained 6-sulfonic acid from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-4,6-disulfonic acid with 1 mole of 1,4-diaminobenzene-3,6- disulfonic acid187 2 moles of 6-.beta.-sulfatoethyl- reaction product of 2 moles of bluish-tinged sulfonyl-2-amino-naphthalene- primary condensation product redained 1-sulfonic acid from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-4,6-disulfonic acid with 1 mole of 1,4-diaminobenzene-3,6- disulfonic acid188 2 moles of aniline-4-.beta.-sulfato- reaction product of 2 moles of orange ethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-methylamino-5-hydroxy- naphthalene-7-sulfonic acid with 1 mole of di-(3-amino-4-sulfophenyl)- sulfone189 2 moles of aniline-4-.beta.-thio- reaction product of 2 moles of orange sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-methylamino-5-hydroxy- naphthalene-7-sulfonic acid with 1 mole of di-(3-amino-4-sulfophenyl)- sulfone190 2 moles of aniline-3-.beta.- reaction product of 2 moles of orange sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-methylamino-5-hydroxy- naphthalene-7-sulfonic acid with 1 mole of di-(3-amino-4-sulfophenyl)- sulfone191 2 moles of 2-aminoanisole-4- reaction product of 2 moles of orange .beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-methylamino-5-hydroxy- naphthalene-7-sulfonic acid with 1 mole of di-(3-amino-4-sulfophenyl)- sulfone192 2 moles of 2-methoxy-5-methyl- reaction product of 2 moles of reddish- aniline-4-.beta.-sulfatoethylsulfone primary condensation product tinged orange from equimolar amounts of cyanuric chloride and 2-methylamino-5-hydroxy- naphthalene-7-sulfonic acid with 1 mole of di-(3-amino-4-sulfophenyl)- sulfone193 2 moles of aniline-4-.beta.-sulfato- reaction product of 2 moles of red ethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 4,4'-diamino-diphenyl-sulfone194 2 moles of 8-.beta.-sulfatoethyl- reaction product of 2 moles of bluish-tinged sulfonyl-2-amino-naphthalene- primary condensation product redained 6-sulfonic acid from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 4,4'-diamino-diphenyl-sulfone195 2 moles of 6-.beta.-sulfatoethyl- reaction product of 2 moles of bluish-tinged sulfonyl-2-amino-naphthalene- primary condensation product redained 1-sulfonic acid from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 4,4'-diamino-diphenyl-sulfone196 2 moles of 2,5-dimethoxy- reaction product of 2 moles of claret aniline-4-.beta.-sulfatoethyl- primary condensation product obtained sulfone from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-4,6-disulfonic acid with 1 mole of 4,4'-diamino-diphenylure- 3,3'-disulfonic acid197 2 moles of aniline-4-.beta.- reaction product of 2 moles of red sulfatoethylsulfone secondary condensation product obtained from equimolar amounts of cyanuric chloride, 1-amino-8-hydroxynaphthalene- 3,6-disulfonic acid and aniline-3- sulfonic acid with 1 mole of 2,2'-di- chloro-4,4'-diaminodiphenyl198 2 moles of 2-aminoanisole-4- reaction product of 2 moles of bluish-tinged .beta.-thiosulfatoethylsulfone secondary condensation product redained from equimolar amounts of cyanuric chloride, 1-amino-8-hydroxynaphthalene- 3,6-disulfonic acid and aniline-3- sulfonic acid with 1 mole of 2,2'-di- chloro-4,4'-diaminodiphenyl199 2 moles of aniline-3-vinyl- reaction product of 2 moles of red sulfone secondary condensation product obtained from equimolar amounts of cyanuric chloride, 1-amino-8-hydroxynaphthalene-3,6-disul- fonic acid and 2-amino-ethanol with 1 mole of 4,4'-diaminodiphenyl-3,3'-dicarboxylic acid200 2 moles of 2,6-dimethylaniline- reaction product of 2 moles of red 4-.beta.-sulfatoethylsulfone secondary condensation product obtained from equimolar amounts of cyanuric chloride, 1-amino-8-hydroxynaphthalene- 3,6-disulfonic acid and .beta.-sulfatoethyl- amine with 1 mole of 2,7-diamino- carbazole201 2 moles of aniline-4-.beta.- reaction product of 2 moles of red sulfatoethylsulfone secondary condensation product obtained from equimolar amounts of cyanuric chloride, 1-amino-8-hydroxynaphthalene- 3,6-disulfonic acid and isopropanol with 1 mole of 3-ethoxy-4,4'-diamino- diphenyl202 2 moles of aniline-3-.beta.- reaction product of 2 moles of red sulfatoethylsulfone secondary condensation product obtained from equimolar amounts of cyanuric chloride, 1-amino-8-hydroxynaphthalene- 3,6-disulfonic acid and isopropanol with 1 mole of 3-ethoxy-4,4'-diamino- diphenyl203 2 moles of aniline-3-.beta.- reaction product of 2 moles of red sulfatoethylsulfone secondary condensation product obtained from equimolar amounts of cyanuric chloride, 1-amino-8-hydroxynaphthalene- 4,6-disulfonic acid and thioglycollic acid with 1 mole of 3,3'-dichloro-4,4'- diamino-diphenyl204 2 moles of 2-aminoanisole- reaction product of 2 moles of bluish-tinged 5-.beta.-sulfatoethylsulfone secondary condensation product redained from equimolar amounts of cyanuric chloride, 1-amino-8-hydroxynaphthalene- 4,6-disulfonic acid and thioglycollic acid with 1 mole of 3,3'-dichloro-4,4'- diamino-diphenyl205 2 moles of 2-aminoanisole-4-.beta.- reaction product of the orange sulfatoethylsulfone secondary condensation product obtained from equimolar amounts of cyanuric chloride, 2-amino-5-hydroxynaphthalene- 7-sulfonic acid and methyltaurine with 1 mole of 2,7-diaminodiphenylsulfone206 2 moles of 2-aminotoluene-4- reaction product of 2 moles of orange .beta.-sulfatoethylsulfone secondary condensation product obtained from equimolar amounts of cyanuric chloride, 2-amino-5-hydroxynaphthalene- 7-sulfonic acid and methyltaurine with 1 mole of 2,7-diaminodiphenylsulfone207 2 moles of 2-methoxy-5-methyl- reaction product of 2 moles of red aniline-4-.beta.-sulfatoethyl- secondary condensation product obtained sulfone from equimolar amounts of cyanuric chloride, 2-amino-8-hydroxynaphthalene- 6-sulfonic acid and .beta.-aminopropionic acid with 1 mole of 2,2'-dichloro-5,5'- dimethoxy-4,4'-diaminodiphenyl208 2 moles of 2,5-dimethoxy- reaction product of 2 moles of claret aniline-4-.beta.-sulfatoethyl- secondary condensation product obtained sulfone from equimolar amounts of cyanuric chloride, 1-amino-8-hydroxynaphthalene- 3,6-disulfonic acid and .beta.-methoxyethyl- amine with 1 mole of 2,2'-dimethoxy- 5,5'-disulfo-4,4'-diamino-diphenylurea209 2 moles of 2-chloroaniline- reaction product of 2 moles of red 5-.beta.-sulfatoethylsulfone secondary condensation product obtained from equimolar amounts of cyanuric chloride, 1-amino-8-hydroxynaphthalene- 3,6-disulfonic acid and .beta.-methoxyethyl- amine with 1 mole of 2,2'-dimethoxy- 5,5'-disulfo-4,4'-diamino-diphenylurea210 2 moles of 2,6-dimethylaniline- reaction product of 2 moles of red 4-.beta.-sulfatoethylsulfone secondary condensation product obtained from equimolar amounts of cyanuric chloride, 1-amino-8-hydroxynaphthalene- 4,6-disulfonic acid and aniline-N- methanesulfonic acid with 1 mole of benzidine211 2 moles of 2,6-dimethylaniline- reaction product of 2 moles of red 3-.beta.-sulfatoethylsulfone secondary condensation product obtained from equimolar amounts of cyanuric chloride, 1-amino-8-hydroxynaphthalene- 4,6-disulfonic acid and aniline-N- methanesulfonic acid with 1 mole of benzidine212 2 moles of 2,4-dimethoxyaniline- reaction product of 2 moles of claret 5-.beta.-sulfatoethylsulfone secondary condensation product obtained from equimolar amounts of cyanuric chloride, 1-amino-8-hydroxynaphthalene- 3,6-disulfonic acid and p-aminobenzoic acid with 1 mole of 4,4'-diamino- diphenyl-sulfide-2,2'-disulfonic acid213 2 moles of 2-aminoanisole-4- reaction product of 2 moles of bluish-tinged .beta.-thiosulfatoethylsulfone secondary condensation product redained from equimolar amounts of cyanuric chloride, 1-amino-8-hydroxynaphthalene- 3,6-disulfonic acid and p-aminobenzoic acid with 1 mole of 4,4'-diamino- diphenyl-sulfide-2,2'-disulfonic acid214 2 moles of aniline-4-.beta.-thio- reaction product of 2 moles of bluish-tinged sulfatoethylsulfone secondary condensation product redained from equimolar amounts of cyanuric chloride, 1-amino-8-hydroxynaphthalene- 3,6-disulfonic acid and aniline-2,5- disulfonic acid with 1 mole of 2,5- bis-(4'-aminophenyl)-1,3,4-oxadiazole215 2 moles of 4-aminoanisole-2- reaction product of 2 moles of bluish-tinged .beta.-sulfatoethylsulfone secondary condensation product redained from equimolar amounts of cyanuric chloride, 1-amino-8-hydroxynaphthalene- 3,6-disulfonic acid and aniline-2,5- disulfonic acid with 1 mole of 2,5- bis-(4'-aminophenyl)-1,3,4-oxadiazole216 2 moles of 4-.beta.-sulfatoethyl- reaction product of 2 moles of red sulfonyl-aniline-2-sulfonic secondary condensation product acid obtained from equimolar amounts of cyanuric chloride, 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid and aniline-2,5-disulfonic acid with 1 mole of 2,5-bis-(4'-aminophenyl)- 1,3,4-oxadiazole217 2 moles of 4-aminotoluene- reaction product of 2 moles of red 2-.beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-4,6-disulfonic acid with 1 mole of 4,4'-diamino-2-sulfo- diphenyl ether218 2 moles of 2-aminoanisole- reaction product of 2 moles of bluish-tinged 4-vinyl-sulfone primary condensation product redained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-4,6-disulfonic acid with 1 mole of 4,4'-diamino-2-sulfo- diphenyl ether219 2 moles of aniline-4-vinyl- reaction product of 2 moles of red sulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,5-diaminonaphthalene220 2 moles of aniline-3-vinyl- reaction product of 2 moles of red sulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,5-diaminonaphthalene221 2 moles of 2-bromoaniline-4- reaction product of 2 moles of red .beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,5-diaminonaphthalene222 2 moles of 2,6-dichloroaniline- reaction product of 2 moles of red 4-.beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of .alpha.,.beta.-bis-(4-aminophenoxy)- ethane223 2 moles of 6-.beta.-sulfatoethyl- reaction product of 2 moles of bluish-tinged sulfonyl-2-amino-naphthalene- primary condensation product redained 1-sulfonic acid from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of .alpha.,.beta.-bis-(4-aminophenoxy)- ethane224 2 moles of 2-naphthylamine-5- reaction product of 2 moles of bluish-tinged .beta.-sulfatoethylsulfone primary condensation product redained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of .alpha.,.beta.-bis-(4-aminophenoxy)- ethane225 2 moles of 2-naphthylamine-8- reaction product of 2 moles of bluish-tinged .beta.-sulfatoethylsulfone primary condensation product redained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of .alpha.,.beta.-bis-(4-aminophenoxy)- ethane226 2 moles of 2-naphthylamine-6- reaction product of 2 moles of bluish-tinged .beta.-sulfatoethylsulfone primary condensation product redained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of .alpha.,.beta.-bis-(4-aminophenoxy)- ethane227 2 moles of 2-chloroaniline-4- reaction product of 2 moles of red .beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of .alpha.,.beta.-bis-(4-aminophenoxy)- ethane228 2 moles of 2-amino-4-.beta.-sulfato- reaction product of 2 moles of red ethylsulfonyl-benzoic acid primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of .alpha.,.beta.-bis-(4-aminophenoxy)- ethane229 2 moles of 5-.beta.-sulfatoethyl- reaction product of 2 moles of red sulfonyl-aniline-2-sulfonic primary condensation product obtained acid from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of .alpha.,.beta.-bis-(4-aminophenoxy)- ethane230 2 moles of aniline-4-.beta.- reaction product of 1 mole of red sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid and 1 mole of the primary condensation product obtained from equimolar amounts of cyanuric chloride and 1- amino-8-hydroxynaphthalene-4,6- disulfonic acid with 1 mole of 4,4'- diamino-diphenylamine-3-sulfonic acid231 2 moles of aniline-3-.beta.- reaction product of 1 mole of yellowish- sulfatoethylsulfone primary condensation product tinged red from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid and 1 mole of the primary condensation product obtained from equimolar amounts of cyanuric chloride and 2- amino-5-naphthol-7-sulfonic acid with 1 mole of 1,4-diamino-2- methoxybenzene-5-sulfonic acid232 2 moles of aniline-4-.beta.- reaction product of 1 mole of red thiosulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid and 1 mole of the primary condensation pro- duct obtained from equimolar amounts of cyanuric chloride and 2-amino-8- naphthol-6-sulfonic acid with 1 mole of 1,3-diamino-4-methoxybenzene233 2 moles of aniline-4-vinyl- reaction product of 1 mole of red sulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxynaphthalene- 3,6-disulfonic acid and 1 mole of the primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-naphthol-6-sulfonic acid with 1 mole of 1,3-diamino-4-methoxybenzene234 2 moles of 2-aminoanisole-4- reaction product of 1 mole of red .beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxynaphthalene- 3,6-disulfonic acid and 1 mole of the primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxynaphthalene- 6-sulfonic acid with 1 mole of 1,4-diamino- benzene-3-sulfonic acid235 2 moles of 2-methoxy-5-methyl- reaction product of 1 mole of bluish-tinged aniline-4-.beta.-sulfatoethyl- primary condensation product redained sulfone from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxynaphthalene- 3,6-disulfonic acid and 1 mole of the primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxynaphthalene- 6-sulfonic acid with 1 mole of 1,4-diamino- benzene-3-sulfonic acid236 2 moles of 2,5-dimethoxy- reaction product of 1 mole of bluish-tinged aniline-4-.beta.-sulfatoethyl- primary condensation product redained sulfone from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxynaphthalene- 3,6-disulfonic acid and 1 mole of the primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxynaphthalene- 6-sulfonic acid with 1 mole of 1,4-diamino- benzene-3-sulfonic acid237 2 moles of 8-.beta.-sulfatoethyl- reaction product of 1 mole of bluish-tinged sulfonyl-2-amino-naphthalene- primary condensation product redained 6-sulfonic acid from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxynaphthalene- 3,6-disulfonic acid and 1 mole of the primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxynaphthalene- 6-sulfonic acid with 1 mole of 1,4-diamino- benzene-3-sulfonic acid238 2 moles of 6-.beta.-sulfatoethyl- reaction product of 1 mole of bluish-tinged sulfonyl-2-amino-naphthalene- primary condensation product redained 1-sulfonic acid from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid and 1 mole of the primary condensation pro- duct obtained from equimolar amounts of cyanuric chloride and 2-amino-8- hydroxynaphthalene-6-sulfonic acid with 1 mole of 1,4-diaminobenzene- 3-sulfonic acid239 2 moles of 2-naphthylamine-6- reaction product of 1 mole of bluish-tinged .beta.-sulfatoethylsulfone primary condensation product redained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid and 1 mole of the primary condensation pro- duct obtained from equimolar amounts of cyanuric chloride and 2-amino-8- hydroxynaphthalene-6-sulfonic acid with 1 mole of 1,4-diaminobenzene- 3-sulfonic acid240 2 moles of 2-naphthylamine-8- reaction product of 1 mole of bluish-tinged .beta.-sulfatoethylsulfone primary condensation product redained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid and 1 mole of the primary condensation pro- duct obtained from equimolar amounts of cyanuric chloride and 2-amino-8- hydroxynaphthalene-6-sulfonic acid with 1 mole of 1,4-diaminobenzene- 3-sulfonic acid241 2 moles of 2-naphthylamine-5- reaction product of 1 mole of bluish-tinged .beta.-sulfatoethylsulfone primary condensation product redained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid and 1 mole of the primary condensation pro- duct obtained from equimolar amounts of cyanuric chloride and 2-amino-8- hydroxynaphthalene-6-sulfonic acid with 1 mole of 1,4-diaminobenzene- 3-sulfonic acid242 2 moles of aniline-4-.beta.- reaction product of 1 mole of red sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-4,6-disulfonic acid and 1 mole of the primary condensation product obtained from equimolar amounts of cyanuric chloride and 2- amino-8-hydroxynaphthalene-6- sulfonic acid with 1 mole of 1,3- diaminobenzene-4-sulfonic acid243 2 moles of aniline-3-.beta.- reaction product of 1 mole of red sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-4,6-disulfonic acid and 1 mole of the primary condensation pro- duct obtained from equimolar amounts of cyanuric chloride and 2-amino-8- hydroxynaphthalene-6-sulfonic acid with 1 mole of 1,3-diaminobenzene-1- sulfonic acid244 2 moles of aniline-4-vinyl- reaction product of 1 mole of orange sulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-6-sulfonic acid and 1 mole of the primary condensation pro- duct obtained from equimolar amounts of cyanuric chloride and 2-amino-5- naphthol-7-sulfonic acid with 1 mole of 1,4-diaminobenzene-3-sulfonic acid245 2 moles of aniline-4-.beta.-thio- reaction product of 1 mole of orange sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-6-sulfonic acid and 1 mole of the primary condensation pro- duct obtained from equimolar amounts of cyanuric chloride and 2-amino-5- naphthol-7-sulfonic acid with 1 mole of 1,4-diaminobenzene-3-sulfonic acid246 2 moles of 2-aminoanisole-4- reaction product of 1 mole of orange .beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-hydroxy- naphthalene-6-sulfonic acid and 1 mole of the primary condensation pro- duct obtained from equimolar amounts of cyanuric chloride and 2-amino-5- naphthol-7-sulfonic acid with 1 mole of 1,4-diaminobenzene-3-sulfonic acid247 2 moles of aniline-3-vinyl- reaction product of 2 moles of red sulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 4,4'-diaminoazobenzene248 2 moles of 2-aminoanisole-4- reaction product of 2 moles of claret .beta.-thiosulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 4,4'-diaminoazobenzene249 2 moles of 2,5-dimethoxy- reaction product of 2 moles of red aniline-4-.beta.-sulfatoethyl- primary condensation product obtained sulfone from equimolar amounts of cyanuric chloride and 2-methylamino-8-naphthol- 6-sulfonic acid with 1 mole of 4,4'- diaminodiphenylmethane250 2 moles of 2-methoxy-5-methyl- reaction product of 2 moles of claret aniline-4-.beta.-sulfatoethyl- primary condensation product obtained sulfone from equimolar amounts of cyanuric chloride and 1-amino-8-hydroxy- naphthalene-3,6-disulfonic acid with 1 mole of 1,2-bis-(4'-aminophenyl)- ethane__________________________________________________________________________
EXAMPLE 251
18.5 parts by weight of cyanuric chloride are dissolved in 60 parts by volume of acetone, with warming, and the solution is then poured into 500 parts by volume of water at 15.degree.-20.degree. C. A neutral solution of 31.9 parts by weight of 1-amino-8-naphthol-3,6-disulfonic acid and 8.5 parts by volume of aqueous 33% sodium hydroxide solution in 150 parts by volume of water is then added immediately and the resulting mixture is stirred for some time. A neutral solution of 18.5 parts by weight of 4,4'-diaminostilbene-2,2'-disulfonic acid and 9 parts by volume of aqueous 33% sodium hydroxide solution in 250 parts by volume of water and, immediately thereafter, 30 parts by weight of crystalline sodium acetate are added and the resulting mixture is stirred for several hours at 20.degree.-30.degree. C. The suspension of the coupling component which is thus obtained is combined with the following diazonium salt solution: 29.7 parts by weight of 4-.beta.-sulfatoethylsulfonyl-2-aminophenol are suspended in 140 parts by volume of water and 60 parts by weight of ice and dissolved to give a neutral solution by adding 7.6 parts by weight of sodium carbonate. 20.5 parts by volume of aqueous 5 N sodium nitrite solution are added and the solution thus obtained is added dropwise to a mixture of 25 parts by volume of aqueous 31% hydrochloric acid and 150 parts by weight of ice. The pH value is adjusted to 5.5-6.5 by adding 13 parts by weight of sodium bicarbonate in portions, and the suspension of the coupling component described initially is then added. The coupling reaction is carried out for several hours at 22.degree.-24.degree. C., the pH value being kept at 6.0 by adding a total of 19.5 parts by weight of sodium bicarbonate in portions. After the formation of the dyestuff has ended, the mixture is warmed to about 80.degree. C. and the dyestuff solution is clarified. The solution is allowed to cool to 50.degree. C. and 30 parts by weight of crystalline sodium acetate and 24.7 parts by weight of crystalline copper sulfate are added and the mixture is stirred for one hour at 50.degree.-55.degree. C. The dyestuff is precipitated by adding 25%, based on the volume, of potassium chloride, filtered off, dried in vacuo at 60.degree. C. and ground. This gives a brown-black dyestuff powder which gives reddish-tinged violet dyeings and prints of considerable depth of shade on cotton when the processes customary for reactive dyestuffs are used. The dyestuff has the following constitution: ##STR106##
EXAMPLE 252
If the corresponding amount of 5-.beta.-sulfatoethylsulfonyl-2-aminophenol is employed in place of the 4-.beta.-sulfatoethylsulfonyl-2-aminophenol in Example 251 and in other respects the procedure is as indicated in Example 251, this gives a dark brown dyestuff powder with which deep violet dyeings with very good general fastness properties are obtained on cellulose materials. In the form of the free acid, the dyestuff has the following constitution: ##STR107##
EXAMPLE 253
The reaction product of 18.5 parts by weight of 4,4'-diaminostilbene-2,2'-disulfonic acid with the primary condensation product of 31.9 parts by weight of 1-amino-8-hydroxynaphthalene-3,6-disulfonic acid and 18.5 parts by weight of cyanuric chloride is prepared in the manner described in Example 251. The suspension of this coupling component is combined with the following diazonium salt solution:
25.1 parts by weight of 2-aminonaphthalene-8-.beta.-hydroxyethylsulfone are introduced into 66 parts by volume of 20% strength oleum in the course of about 20 minutes and the mixture is then warmed at 65.degree.-70.degree. C. for 4 hours. The reaction mixture is then cooled to 25.degree.-30.degree. C. and is allowed to run into a mixture of 250 parts by weight of ice and 100 parts by volume of water. The diazotization is then carried out at 0.degree.-5.degree. C. with 20 parts by volume of aqueous 5 N sodium nitrite solution, the reaction mixture is stirred for a further one hour at this temperature and then a little excess nitrous acid is destroyed by means of amidosulfonic acid. The pH of the diazonium salt solution is adjusted to 5.0-5.5 by adding 120 parts by weight of calcium carbonate and the solution is added to the abovementioned suspension of the coupling component.
After the diazonium salt solution has been added, the mixture is stirred for 16 hours at room temperature, the pH value being kept at 5.5-6.0 by adding about 10.1 parts by weight of calcium carbonate in portions. The mixture is then warmed to 60.degree.-70.degree. C. and the gypsum is filtered off. The latter is washed with hot water, and 30 parts by weight of crystalline sodium acetate and 24.7 parts by weight of crystalline copper sulfate are then added to the filtrate and a mixture of 22.7 parts by weight of 30% strength hydrogen peroxide and 100 parts by volume of water is added dropwise at 32.degree.-38.degree. C. in the course of 30 minutes. After 3 hours, the dyestuff solution is clarified and the dyestuff is precipitated by adding potassium chloride, filtered off and dried in vacuo at 60.degree. C. This gives a dark blue powder which gives reddish-tinged blue prints and dyeings on cotton fabric. In the form of the free acid, the dyestuff has the following constitution: ##STR108##
EXAMPLE 253a
The non-metallized dyestuff is prepared as described in Example 251. After clarifying, 30 parts by weight of crystalline sodium acetate and 29.5 parts by weight of crystalline cobalt sulfate are added to the filtrate and the mixture is then warmed at 60.degree.-65.degree. C. for 2 hours. The dyestuff solution is clarified and then evaporated to dryness in vacuo. This gives a dark dyestuff powder with which opaque violet prints can be produced on cotton in the presence of acid-binding agents. In the form of the free acid, the dyestuff has the following constitution: ##STR109##
EXAMPLE 254
The non-metallized dyestuff is prepared as described in Example 251. After clarifying, the filtrate is warmed to 50.degree.-55.degree. C. and, at this temperature, 32 parts by weight of crystalline sodium acetate and 25 parts by weight of chromium-potassium sulfate are added. The temperature is then raised to the boiling point and the mixture is boiled under reflux for 5 hours. Thereafter, the dyestuff solution is clarified and then evaporated to dryness in vacuo at 60.degree. C. This gives a grey-black dyestuff powder with which reddish-tinged grey prints are obtained on cotton fabric in the presence of acid-binding agents. In the form of the free acid, the dyestuff has the following constitution: ##STR110##
EXAMPLE 255
32.5 parts by weight of 2-methoxy-5-methylaniline-4-.beta.-sulfatoethylsulfone are suspended in 150 parts by volume of water and 50 parts by weight of ice and dissolved by adding about 6.3 parts by weight of calcined sodium carbonate, the pH value being between 6.0 and 6.5. 20.3 parts by volume of aqueous 5 N sodium nitrite solution and 1.5 parts by weight of kieselguhr are added and the solution is clarified. The filtrate runs at 0.degree.-5.degree. C. into a mixture of 150 parts by weight of ice and 28.2 parts by weight of aqueous 31% hydrochloric acid. After stirring for one hour at 0.degree.-5.degree. C., a little excess nitrous acid is destroyed with amidosulfonic acid and the pH of the resulting diazonium salt solution is then adjusted to 6 by introducing about 4 parts by weight of sodium bicarbonate. This solution is combined with the coupling solution described in Example 251. The coupling reaction is carried out at 18.degree.-20.degree. C. for several hours, the pH value being kept at 5.3-6.1 by adding sodium bicarbonate in portions. When the coupling has ended, a solution of 34.6 parts by weight of crystalline copper sulfate, 48.3 parts by weight of crystalline sodium acetate and 31.8 parts by weight of glacial acetic acid in 147.5 parts by volume of water is added and the resulting mixture is then boiled under reflux for 18 hours. After cooling, the dyestuff solution is clarified and the dyestuff is then precipitated by adding potassium chloride, filtered off and dried in vacuo at 60.degree. C. This gives a blue-black powder which in the presence of acid-binding agents dyes cellulose materials in reddish-tinged blue shades. In the form of the free acid, the dyestuff has the following constitution: ##STR111##
The heavy metal complex dyestuffs listed in the table which follows can be obtained in a manner similar to that described in Examples 251 to 255. In the "diazo component" column, the said components are indicated in the form in which they are present after metallization, that is to say in some cases with a hydroxyl group formed from a methoxy group by demethylating metallization or with a hydroxy group introduced by oxidative coppering.
TABLE 2__________________________________________________________________________ Complex-Example forming Color shadeNo. Diazo component Coupling component metal on__________________________________________________________________________ cotton256 2 moles of 2-aminophenol- reaction product of 2 moles of the chromium bluish-tinged 5-.beta.-sulfatoethylsulfone primary condensation product grey obtained from equimolar amounts of cyanuric chloride and 1-amino-8- hydroxynaphthalene-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid257 2 moles of 2-aminophenol- reaction product of 2 moles of the cobalt violet-tinged 5-.beta.-sulfatoethylsulfone primary condensation product grey obtained from equimolar amounts of cyanuric chloride and 1-amino-8- hydroxynaphthalene-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'disulfonic acid258 2 moles of 6-bromo-2-amino- reaction product of 2 moles of the copper violet phenol-4-.beta.-sulfatoethyl- primary condensation product sulfone obtained from equimolar amounts of cyanuric chloride and 1-amino-8- hydroxynaphthalene-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid259 2 moles of 6-bromo-2-amino- reaction product of 2 moles of the chromium reddish-tinged phenol-4-.beta.-sulfatoethyl- primary condensation product grey sulfone obtained from equimolar amounts of cyanuric chloride and 1-amino-8- hydroxynaphthalene-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid260 2 moles of 6-bromo-2-amino- reaction product of 2 moles of the cobalt opaque violet phenol-4-.beta.-sulfatoethyl- primary condensation product sulfone obtained from equimolar amounts of cyanuric chloride and 1-amino-8- hydroxynaphthalene-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid261 2 moles of b-nitro-2-amino reaction product of 2 moles of the copper violet phenol-4-.beta.-sulfatoethyl- primary condensation product sulfone obtained from equimolar amounts of cyanuric chloride and 1-amino-8- hydroxynaphthalene-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid262 2 moles of 6-nitro-2-amino- reaction product of 2 moles of the chromium grey phenol-4-.beta.-sulfatoethyl- primary condensation product sulfone obtained from equimolar amounts of cyanuric chloride and 1-amino-8- hydroxynaphthalene-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid263 2 moles of 6-nitro-2-amino- reaction product of 2 moles of the cobalt grey phenol-4-.beta.-sulfatoethyl- primary condensation product sulfone obtained from equimolar amounts of cyanuric chloride and 1-amino-8- hydroxynaphthalene-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid264 2 moles of 4-methyl-2-amino- reaction product of 2 moles of the chromium bluish-tinged phenol-5-.beta.-sulfatoethyl- primary condensation product grey sulfone obtained from equimolar amounts of cyanuric chloride and 1-amino-8- hydroxynaphthalene-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid265 2 moles of 4-methyl-2-amino- reaction product of 2 moles of the cobalt violet-tinged phenol-5-.beta.-sulfatoethyl- primary condensation product grey sulfone obtained from equimolar amounts of cyanuric chloride and 1-amino-8- hydroxynaphthalene-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid266 2 moles of 4-methoxy-2-amino- reaction product of 2 moles of the copper reddish-tinged phenol-5-.beta.-sulfatoethyl- primary condensation product blue sulfone obtained from equimolar amounts of cyanuric chloride and 1-amino-8- hydroxynaphthalene-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid267 2 moles of 4-.beta.-sulfatoethyl- reaction product of 2 moles of the copper violet sulfonyl-2-aminophenol-6- primary condensation product sulfonic acid obtained from equimolar amounts of cyanuric chloride and 1-amino-8- hydroxynaphthalene-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid268 2 moles of 4-.beta.-sulfatoethyl- reaction product of 2 moles of the chromium reddish-tinged sulfonyl-2-aminophenol-6- primary condensation product grey sulfonic acid obtained from equimolar amounts of cyanuric chloride and 1-amino-8- hydroxynaphthalene-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid269 2 moles of 4-.beta.-sulfatoethyl- reaction product of 2 moles of the cobalt opaque violet sulfonyl-2-aminophenol-6- primary condensation product sulfonic acid obtained from equimolar amounts of cyanuric chloride and 1-amino-8- hydroxynaphthalene-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid270 2 moles of 8-.beta.-sulfatoethyl- reaction product of 2 moles of the copper reddish-tinged sulfonyl-1-hydroxy-2-amino- primary condensation product blue naphthalene-6-sulfonic acid obtained from equimolar amounts of cyanuric chloride and 1-amino-8- hydroxynaphthalene-3,6-disulfonic acid with 1 mole of 4,4'-diamino- stilbene-2,2'-disulfonic acid271 2 moles of 2-aminophenol- reaction product of 2 moles of the copper violet 4-.beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino- 8-hydroxynaphthalene-3,6-disul- fonic acid with 1 mole of 3,3'- dimethyl-benzidine-6,6'-disulfonic acid272 2 moles of 2-aminophenol- reaction product of 2 moles of chromium reddish-tinged 4-.beta.-sulfatoethylsulfone the primary condensation product grey obtained from equimolar amounts of cyanuric chloride and 1-amino- 8-hydroxynaphthalene-3,6-disul- fonic acid with 1 mole of 3,3'- dimethyl-benzidine-6,6'-disulfonic acid273 2 moles of 2-aminophenol- reaction product of 2 moles of cobalt opaque violet 4-.beta.-sulfatoethylfulfone the primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino- 8-hydroxynaphthalene-3,6-disul- fonic acid with 1 mole of 3,3'- dimethyl-benzidine-6,6'-disulfonic acid274 2 moles of 2-aminophenol- reaction product of 2 moles of copper violet 5-.beta.-sulfatoethylsulfone the primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino- 8-hydroxynaphthalene-3,6-disul- fonic acid with 1 mole of 3,3'- dimethyl-benzidine-6,6'-disulfonic acid275 2 moles of 2-aminophenol- reaction product of 2 moles of chromium bluish-tinged 5-.beta.-sulfatoethylsulfone the primary condensation product grey obtained from equimolar amounts of cyanuric chloride and 1-amino- 8-hydroxynaphthalene-3,6-disul- fonic acid with 1 mole of 3,3'- dimethyl-benzidine-6,6'-disulfonic acid276 2 moles of 2-aminophenol- reaction product of 2 moles of cobalt violet-tinged 5-.beta.-sulfatoethylsulfone the primary condensation product grey obtained from equimolar amounts of cyanuric chloride and 1-amino- 8-hydroxynaphthalene-3,6-disul- fonic acid with 1 mole of 3,3'- dimethyl-benzidine-6,6'-disulfonic acid277 2 moles of 6-chloro-2-amino- reaction product of 2 moles of copper violet phenol-4-.beta.-sulfatoethyl- the primary condensation product sulfone obtained from equimolar amounts of cyanuric chloride and 1-amino- 8-hydroxynaphthalene-3,6-disul- fonic acid with 1 mole of 3,3'- dimethyl-benzidine-6,6'-disulfonic acid278 2 moles of 6-chloro-2-amino- reaction product of 2 moles of chromium reddish-tinged phenol-4-.beta.-sulfatoethyl- the primary condensation product grey sulfone obtained from equimolar amounts of cyanuric chloride and 1-amino- 8-hydroxynaphthalene-3,6-disul- fonic acid with 1 mole of 3,3'- dimethyl-benzidine-6,6'-disulfonic acid279 2 moles of 6-chloro-2-amino- reaction product of 2 moles of cobalt opaque violet phenol-4-.beta.-sulfatoethyl- the primary condensation product sulfone obtained from equimolar amounts of cyanuric chloride and 1-amino- 8-hydroxynaphthalene-3,6-disul- fonic acid with 1 mole of 3,3'- dimethyl-benzidine-6,6'-disulfonic acid280 2 moles of 2-aminophenol- reaction product of 2 moles of copper violet 4-.beta.-sulfatoethylsulfone the primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid with 1 mole of 1,6-diaminohexane281 2 moles of 2-aminophenol- reaction product of 2 moles of chromium reddish-tinged 4-.beta.-sulfatoethylsulfone the primary condensation product grey obtained from equimolar amounts of cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid with 1 mole of 1,6-diaminohexane282 2 moles of 2-aminophenol- reaction product of 2 moles of cobalt violet 4-.beta.-sulfatoethylsulfone the primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid with 1 mole of 1,6-diaminohexane283 2 moles of 2-aminophenol- reaction product of 2 moles of copper violet 5-.beta.-sulfatoethylsulfone the primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid with 1 mole of 1,6-diaminohexane284 2 moles of 2-aminophenol- reaction product of 2 moles of chromium bluish-tinged 5-.beta.-sulfatoethylsulfone the primary condensation product grey obtained from equimolar amounts of cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid with 1 mole of 1,6-diaminohexane285 2 moles of 2-aminophenol- reaction product of 2 moles of cobalt violet-tinged 5-.beta.-sulfatoethylsulfone the primary condensation product grey obtained from equimolar amounts of cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid with 1 mole of 1,6-diaminohexane286 2 moles of 8-.beta.-sulfato- reaction product of 2 moles of copper reddish-tinged ethylsulfonyl-1-hydroxy-2- the primary condensation product blue amino-naphthalene-6- obtained from equimolar amounts of sulfonic acid cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid with 1 mole of 1,6-diaminohexane287 2 moles of 2-aminophenol- reaction product of 2 moles of copper violet 4-.beta.-sulfatoethylsulfone the primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino- 8-naphthol-3,6-disulfonic acid with 1 mole of di-(3-amino-4-sulfophenyl)- sulfone288 2 moles of 2-aminophenol- reaction product of 2 moles of chromium reddish-tinged 4-.beta.-sulfatoethylsulfone the primary condensation product grey obtained from equimolar amounts of cyanuric chloride and 1-amino- 8-naphthol-3,6-disulfonic acid with 1 mole of di-(3-amino-4-sulfo- phenyl)-sulfone289 2 moles of 2-aminophenol- reaction product of 1 mole of the cobalt opaque violet 4-.beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino- 8-naphthol-3,6-disulfonic acid with 1 mole of the primary con- densation product obtained from equimolar amounts of cyanuric chloride and 6-amino-2-naphthol- 4-sulfonic acid with 1 mole of 1,4-diaminobenzene-2-sulfonic acid290 2 moles of 2-aminophenol- reaction product of 1 mole of the copper violet 5-.beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino- 8-naphthol-3,6-disulfonic acid with 1 mole of the primary con- densation product obtained from equimolar amounts of cyanuric chloride and 6-amino-2-naphthol- 4-sulfonic acid with 1 mole of 1,4-diaminobenzene-2-sulfonic acid291 2 moles of 2-aminophenol- reaction product of 1 mole of the chromium bluish-tinged 5-.beta.-sulfatoethylsulfone primary condensation product grey obtained from equimolar amounts of cyanuric chloride and 1-amino- 8-naphthol-3,6-disulfonic acid with 1 mole of the primary con- densation product obtained from equimolar amounts of cyanuric chloride and 6-amino-2-naphthol- 4-sulfonic acid with 1 mole of 1,4-diaminobenzene-2-sulfonic acid292 2 moles of 2-aminophenol- reaction product of 1 mole of the cobalt violet-tinged 5-.beta.-sulfatoethylsulfone primary condensation product grey obtained from equimolar amounts of cyanuric chloride and 1-amino- 8-naphthol-3,6-disulfonic acid with 1 mole of the primary con- densation product obtained from equimolar amounts of cyanuric chloride and 6-amino-2-naphthol- 4-sulfonic acid with 1 mole of 1,4-diaminobenzene-2-sulfonic acid293 2 moles of 2-aminophenol- reaction product of 1 mole of the copper violet 4-.beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino- 8-naphthol-3,6-disulfonic acid, 1 mole of the primary conden- sation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-naphthol- 6-sulfonic acid with 1 mole of 1,3-diaminobenzene-4-sulfonic acid294 2 moles of 2-aminophenol- reaction product of 1 mole of the copper violet 4-.beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino- 8-naphthol-3,6-disulfonic acid, 1 mole of the primary conden- sation product obtained from equimolar amounts of cyanuric chloride and 2-amino-5-naphthol- 7-sulfonic acid with 1 mole of 1,4-diaminobenzene-2-sulfonic acid295 2 moles of 2-aminophenol- reaction product of 1 mole of the copper violet 5-.beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino- 8-naphthol-3,6-disulfonic acid, 1 mole of the primary conden- sation product obtained from equimolar amounts of cyanuric chloride and 2-amino-5-napthol- 7-sulfonic acid with 1 mole of 1,4-diaminobenzene-2-sulfonic acid296 2 moles of 2-aminophenol- reaction product of 1 mole of the chromium violet-brown 5-.beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino- 8-naphthol-3,6-disulfonic acid, 1 mole of the primary conden- sation product obtained from equimolar amounts of cyanuric chloride and 2-amino-5-naphthol- 7-sulfonic acid with 1 mole of 1,4-diaminobenzene-2-sulfonic acid297 2 moles of 2-aminophenol- reaction product of 1 mole of the cobalt brown-violet 5-.beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino- 8-naphthol-3,6-disulfonic acid, 1 mole of the primary conden- sation product obtained from equimolar amounts of cyanuric chloride and 2-amino-5-naphthol- 7-sulfonic acid with 1 mole of 1,4-diaminobenzene-2-sulfonic acid298 2 moles of 8-.beta.-sulfatoethyl- reaction product of 1 mole of the copper reddish-tinged sulfonyl-2-amino-1-naphthol- primary condensation product blue 6-sulfonic acid obtained from equimolar amounts of cyanuric chloride and 1-amino- 8-naphthol-3,6-disulfonic acid, 1 mole of the primary conden- sation product obtained from equimolar amounts of cyanuric chloride and 2-amino-5-naphthol- 7-sulfonic acid with 1 mole of 1,4-diaminobenzene-2-sulfonic acid299 2 moles of 6-bromo-2-amino- reaction product of 1 mole of the copper violet phenol-4-.beta.-sulfatoethyl- primary condensation product sulfone obtained from equimolar amounts of cyanuric chloride and 1-amino- 8-naphthol-3,6-disulfonic acid, 1 mole of the primary conden- sation product obtained from equimolar amounts of cyanuric chloride and 2-amino-5-naphthol- 7-sulfonic acid with 1 mole of 1,4-diaminobenzene-2-sulfonic acid300 2 moles of 6-nitro-2-amino- reaction product of 1 mole of the cobalt brown-black phenol-4-.beta.-sulfatoethyl- primary condensation product sulfone obtained from equimolar amounts of cyanuric chloride and 1-amino- 8-naphthol-3,6-disulfonic acid, 1 mole of the primary conden- sation product obtained from equimolar amounts of cyanuric chloride and 2-amino-5-naphthol- 7-sulfonic acid with 1 mole of 1,4-diaminobenzene-2-sulfonic acid301 2 moles of 2-aminophenol- reaction product of 1 mole of the copper violet 4-.beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino- 8-naphthol-3,6-disulfonic acid, 1 mole of the primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-naphthol-6-sulfonic acid with 1 mole of 1,3-diamino- benzene-4-sulfonic acid302 2 moles of 2-aminophenol- reaction product of 1 mole of the chromium grey-violet 4-.beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid, 1 mole of the primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-naphthol-6-sulfonic acid with 1 mole of 1,3-diamino- benzene-4-sulfonic acid303 2 moles of 2-aminophenol- reaction production of 1 mole of cobalt brown-violet 4-.beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid, 1 mole of the primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-naphthol-6-sulfonic acid with 1 mole of 1,3-diamino- benzene-4-sulfonic acid304 2 moles of 2-aminophenol- reaction production of 1 mole of copper violet 5-.beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid, 1 mole of the primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-naphthol-6-sulfonic acid with 1 mole of 1,3-diamino- benzene-4-sulfonic acid305 2 moles of 2-aminophenol- reaction product of 1 mole of the chromium grey-violet 5-.beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid, 1 mole of the primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-naphthol-6-sulfonic acid with 1 mole of 1,3-diamino- benzene-4-sulfonic acid306 2 moles of 2-aminophenol- reaction product of 1 mole of the cobalt opaque violet 5-.beta.-sulfatoethylsulfone primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid, 1 mole of the primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-naphthol-6-sulfonic acid with 1 mole of 1,3-diamino- benzene-4-sulfonic acid307 2 moles of 4-methyl-2- reaction product of 1 mole of the copper violet aminophenol-5-.beta.-sulfato- primary condensation product ethylsulfone obtained from equimolar amounts of cyanuric chloride and 1-amino-8- naphthol-3,6-disulfonic acid, 1 mole of the primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino-8-naphthol-6-sulfonic acid with 1 mole of 1,3-diamino- benzene-4-sulfonic acid308 2 moles of 2-aminophenol- reaction product of 2 moles of copper claret 4-.beta.-sulfatoethylsulfone the primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino- 5-naphthol-7-sulfonic acid with 1 mole of 1,4-diaminobutane309 2 moles of 2-aminophenol- reaction product of 2 moles of cobalt brown 4-.beta.-sulfatoethylsulfone the primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino- 5-naphthol-7-sulfonic acid with 1 mole of 1,4-diaminobutane310 2 moles of 2-aminophenol- reaction product of 2 moles of chromium black 4-.beta.-sulfatoethylsulfone the primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino- 5-naphthol-7-sulfonic acid with 1 mole of 1,4-diaminobutane311 2 moles of 6-nitro-2-amino- reaction product of 2 moles of chromium black phenol-4-.beta.-sulfatoethyl- the primary condensation product sulfone obtained from equimolar amounts of cyanuric chloride and 2-amino- 5-naphthol-7-sulfonic acid with 1 mole of 1,4-diaminobutane312 2 moles of 6-nitro-2-amino- reaction product of 2 moles of copper red-violet phenol-4-.beta.-sulfatoethyl- the primary condensation product sulfone obtained from equimolar amounts of cyanuric chloride and 2-amino- 5-naphthol-7-sulfonic acid with 1 mole of 1,4-diaminobutane313 2 moles of 2-amino-phenol- reaction product of 2 moles of chromium black-brown 4-.beta.-sulfatoethylsulfone the primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino- 5-naphthol-7-sulfonic acid with 1 mole of 1,3-diaminobenzene-4- sulfonic acid314 2 moles of 2-amino-phenol- reaction product of 2 moles of copper violet 4-.beta.-sulfatoethylsulfone the primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino- 5-naphthol-7-sulfonic acid with 1 mole of 1,3-diaminobenzene-4- sulfonic acid315 2 moles of 2-amino-phenol- reaction product of 2 moles of cobalt brown 4-.beta.-sulfatoethylsulfone the primary condensation product obtained from equimolar amounts of cyanuric chloride and 2-amino- 5-naphthol-7-sulfonic acid with 1 mole of 1,3-diaminobenzene-4- sulfonic acid316 2 moles of 6-nitro-2-amino- reaction product of 2 moles of chromium black phenol-4-.beta.-sulfatoethyl- the primary condensation product sulfone obtained from equimolar amounts of cyanuric chloride and 2-amino- 5-naphthol-7-sulfonic acid with 1 mole of 1,3-diaminobenzene-4- sulfonic acid317 2 moles of 6-nitro-2-amino- reaction product of 2 moles of copper red-violet phenol-4-.beta.-sulfatoethyl- the primary condensation product sulfone obtained from equimolar amounts of cyanuric chloride and 2-amino- 5-naphthol-7-sulfonic acid with 1 mole of 1,3-diaminobenzene-4- sulfonic acid318 2 moles of 2-aminophenol- reaction product of 2 moles of copper red-violet 4-.beta.-sulfatoethylsulfone the primary condensation product obtained from equimolar amounts of cyanuric chloride and 1-amino- 5-naphthol-7-sulfonic acid with 1 mole of 1,5-diaminonaphthalene- 3-sulfonic acid__________________________________________________________________________

Number	Name	Date
3304297	Wegmann	Feb 1967
3591577	Moiso et al.	Jul 1971
3646002	Andrew et al.	Feb 1972
4038267	Sueda et al.	Jul 1977
4054559	Aoki et al.	Oct 1977

Water-soluble disazo dyestuffs

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