Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
  • C09B67/0046—Mixtures of two or more azo dyes
  • C09B67/0055—Mixtures of two or more disazo dyes
  • C09B67/0057—Mixtures of two or more reactive disazo dyes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
  • C09B67/0046—Mixtures of two or more azo dyes
  • C09B67/0055—Mixtures of two or more disazo dyes
  • C09B67/0057—Mixtures of two or more reactive disazo dyes
  • C09B67/0059—Mixtures of two or more reactive disazo dyes all the reactive groups are not directly attached to a heterocyclic system
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
  • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
  • D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
  • D06P1/382—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes reactive group directly attached to heterocyclic group
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
  • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
  • D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
  • D06P1/384—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes reactive group not directly attached to heterocyclic group
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
  • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
  • D06P3/58—Material containing hydroxyl groups
  • D06P3/60—Natural or regenerated cellulose
  • D06P3/66—Natural or regenerated cellulose using reactive dyes
  • D06P3/663—Natural or regenerated cellulose using reactive dyes reactive group directly attached to heterocyclic group
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
  • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
  • D06P3/58—Material containing hydroxyl groups
  • D06P3/60—Natural or regenerated cellulose
  • D06P3/66—Natural or regenerated cellulose using reactive dyes
  • D06P3/666—Natural or regenerated cellulose using reactive dyes reactive group not directly attached to heterocyclic group

Definitions

• This invention relates to black mixtures of fibre reactive azo reactive dyestuffs, containing reactive groups of the vinylsulfone type.
• Dyes have been used over the years in various applications. However, with the evolution of technology and consumer demand, today's requirements in reactive dyes, especially for coloration of cellulose fibres, are high colour yield and good build-up with excellent fastness. Specifically, in the arena of black shades, presently known dyes are mostly mixtures of trisazo, bisazo and monoazo dyes, containing reactive groups of the vinylsulfone types.
• German patent applications DE 19620415 and DE 19655283, as well as the Korean patent application KR 94-2560 disclose ternary mixtures of C.I. Reactive Black 5 with yellow and orange monoazo dyestuffs containing vinylsulfone reactive groups.
• these dyes have certain technical disadvantages and technical limitations such as limited wash fastness as well as contact fastness, due to critical staining on white adjacent fibre materials, especially in regard to staining on polyamide.
• the Japanese patent application JP 17810/1988 discloses black mixtures of C.I. Reactive Black 5 with orange monoazo dyestuffs containing a dichlorotriazinyl fibre reactive group.
• these dyes too have limited build-up in deep shades, low stability to storage in acidic conditions, and limited stability in aqueous solution, high dependency of colour strength and obtained shade on changes in the dyeing conditions, and poor dischargeability.
• JP 160362/1983 discloses black mixtures of C.I. Reactive Black 5 with orange monoazo dyestuffs containing a vinylsulfone fibre reactive group. However, these dyes have limited build-up in deep shades.
• EP 870,807 discloses black mixtures of C.I. Reactive Black 5 with orange monoazo dyestuffs containing two vinylsulfone reactive groups.
• the dyes of the above mentioned patent applications have further limitations such as limited build-up in deep shades, low stability to storage in acidic conditions, and limited stability in aqueous solution, high dependency of color strength and obtained shade on changes in the dyeing conditions, and poor dischargeabilty.
• Consequences of these deficiencies include poor reproducibility, which ultimately affects the economics of the dyeing.
• Black dyestuff composition comprising dyes selected from a) 40-90% of at least one bisazo dyestuff, containing two fibre reactive groups of the vinylsulfone type, which have in the form of the free acid the formula (1 )
• Benzene rings B1 and B2 in formula (1 ) may carry independent from each other 1 -2 additional substituents methoxy, methyl, carboxy or sulfo,
• Y is Vinyl or CH 2 CH 2 L, wherein L is a leaving group which is split off under alkaline conditions, such as sulfato, acetato, halogen, such as chloro or bromo, phosphate, thiosulfato, acyloxy, such as acetoxy or phenoxy, b) up to 20% of at least one bis- or trisazo redbrown, scarlet or rubine dyestuff, containing at least two fibre reactive groups of the vinylsulfone type, which have in the form of the free acid the formula (2)
• DrS0 2 Y and D 2 ' S0 2 Y are independent from each other a radical of the formula
• benzene ring Bi carries 0-2 additional identical of different substituents of C1 - C3-Alkoxy, preferably methoxy, C1 -C3-Alkyl, preferably methyl, Carboxy, halogen, or hydroxyl,
• FV is hydrogen, Sulfomethyl, ⁇ -Sulfoethyl, Carboxymethyl, ⁇ -Carboxyethyl, or ⁇ - Cyanoethyl; c) 10-40% of at least one yellow or orange dyestuffs, containing two fibre reactive groups of the vinylsulfone type, which have in the form of the free acid the formula (3)
• K- is a radical of the benzene or naphthalene series which is substituted by amino, hydroxy, Acylamino, Ureido, and optionally further substituted by 1 or 2 Sulfo groups, and optionally substituted by C1 -C3-Alkoxy, C1 -C3 Alkyl, Halogen, Nitro, or Carboxy.
• K 2 has independent from the meaning of K- one of the meanings of K 1 ; providing that at least one of the radicals K1 or K2 is a radical of the benzene series,
• X is chloro, fluoro, pyridinyl which may be substituted by Carboxy or Carbamoyl, - NHCN, -NHR, -N(CH 3 ) R, -O- R , or -S- R wherein R is C1 -C6-Alkyl which is substituted by at least one sulfo, sulfato, phosphate, thiosulfato or carboxy substituent, and optionally by further substituents such as hydroxy, or the radical of a C1 -C6- primary or secondary aliphatic or C5-C6- cycloaliphatic amine which may be interrupted by heteroatoms O, NH or S, or a heterocyclic radical of the formula wherein W has one of the meanings of R, R a is Hydrogen or C1 -C4-alkyl, which is non-substituted or may be substituted by halogen, hydroxyl, cyano, alkoxy, carb
• R b has each independent from the meaning of R a one of the meanings of R a
• D- is a benzene radical of the formula (3a)
• FIG. 1 showing fastness assessment of dyestuff mixtures A and B
• Figure 2 showing fastness assessment of the dyestuff mixtures C,D and E
• the inventors of the present invention have surprisingly found by means of methodical study that the predicaments highlighted above, are addressed by means of the dye mixture as disclosed hereinafter.
• the mixtures of the present invention contain a) 40-90%, preferably 55-80%, of at least one bisazo dyestuff, containing two fibre reactive groups of the vinylsulfone type, which have in the form of the free acid the formula (1 )
• B1 and B2 are benzene ring radical bearing the substituent -So2Y, wherein Y is Vinyl or CH 2 CH 2 L, wherein L is a leaving group such as sulfato, acetato, halogen, such as chloro or bromo, phosphate, thiosulfato, acyloxy, such as acetoxy or phenoxy; preferably Y is Vinyl or ⁇ -Sulfatoethyl,
• B1 and B2 independent of each other may be further optionally substituted by additional substituents such as methoxy, methyl, carboxy or sulfo; b) up to 20%, preferably 8-18%, of at least one bis- or trisazo redbrown, scarlet or rubine dyestuff, containing at least two fibre reactive groups of the vinylsulfone type, which have in the form of the free acid the formula (2)
• DrS0 2 Y and D 2 ' S0 2 Y are independent from each other radicals of the formula
• Benzene ring carries 0-2 additional identical of different substituents of C1 -C3-Alkoxy, preferably methoxy, C1 -C3-Alkyl, preferably methyl, Carboxy, halogen, or hydroxyl,
• Y has one of the above defined meanings, preferably Vinyl, or ⁇ -sulfatoethyl,
• Ui is hydroxyl or has one of the meanings of Y, preferably Ui is hydroxyl, vinyl or ⁇ - sulfatoethyl,
• FV is hydrogen, Sulfomethylen, ⁇ -Sulfoethylen, Carboxymethyl, ⁇ -Carboxyethyl, or ⁇ - Cyanoethyl; c) 1 0-40%, preferably 12-30%, of at least one yellow or orange dyestuffs, containing two fibre reactive groups of the vinylsulfone type, which have in the form of the free acid the formula (3)
• radicals have the following meaning: is a radical of the benzene or naphthalene series which is substituted by amino, hydroxy, Acylamino, Ureido, and optionally further substituted by 1 or 2 Sulfo groups, and optionally substituted by C1 -C3-Alkoxy, C1 -C3 Alkyl, Halogen, Nitro, or Carboxy.
• K 2 has independent from the meaning of one of the meanings of K 1 ; providing that at least one of the radicals K1 or K2 is a radical of the benzene series, X is halogen, preferably chloro or fluoro, pyridinyl which may be substituted by Carboxy or Carbamoyl, -NHCN, -NHR, -N(CH 3 ) R, -O- R , or -S- R wherein R is C1 -C6-Alkyl, preferably C1 -C3, which is substituted by at least one sulfo, sulfato, phosphate, thiosulfato or carboxy substituent, and optionally by further substituents such as hydroxy, or the radical of a C1 -C6-primary or secondary aliphatic or C5-C6- cycloaliphatic amine which may be interrupted by heteroatoms O, NH or S, or a heterocyclic radical of the formula
• W has one of the meanings of R, preferably ⁇ -Sulfatoethyl, and in particular,
• X is preferably Cyanamino, 2-Sulfoethylamino, N-Methyl- 2-Sulfoethyl-amino, carboxymethylthio, chloro, fluoro, or morpholino, or a radical of the formula
• R a is Hydrogen or C1 -C4-alkyl, which is non-substituted or may be substituted by halogen, hydroxyl, cyano, alkoxy, carboxy and sulfo, preferably Hydrogen or Methyl,
• R b has each independent from the meaning of R a one of the meanings of R a, preferably hydrogen or methyl,
• Y has one of the above defined meanings, preferably is Vinyl, or ⁇ -sulfatoethyl,
• D is a benzene radical of the formula (3a) which may be non substituted or substituted by one or more substituents sulfo, C1 -C4-alkyl, C1 -C4-alkoxy, halogen, or nitro,
• D2 has independent from the meaning of D1 , one of the meanings of D1 .
• K NR a - is preferably a radical of the formula (3b-1 ), (3b-2) and (3b-3) of the benzene or series or a radical of the naphthalene series (3b-4),
• Ro is hydrogen or methyl, preferably hydrogen
• Ri is hydrogen, Methyl, or Ethyl, preferably hydrogen,
• R 2 is amino or methyl, r is 0-1 .
• K 2 -NR b has one of the meanings of (3b-1 ), (3b-2) or (3b-3) wherein the radicals R 0 , Ri, R2 and r have one of the above meanings.
• radicals (3b-1 ) are especially preferred meanings for KiNR a and K 2 NR b .
• the black dyestuff composition may contain up to 20%, preferably 0-10%, of at least one further yellow or orange dyestuffs which have in the form of the free acid the formula the formula (4-1 ) to (4-6), containing at least one vinylsulfone reactive group, providing that the total amount of yellow and orange dyestuffs according to the sum of the components of formula (3) and (4-1 ) to (4-6) is not exceeding 40%.
• the radicals have the following meaning: Q is hydrogen or carboxy, Ac is C1 -C3-Acyl, preferably Acetyl, dichlorotriazinyl or a monohalogen triazinyl ring which is substituted by phenylamino carrying 1 -2 sulfo groups and 0-1 substituents S0 2 Y wherein Y has one of the above defined meanings, preferably Ac is 2,4-dichlorotriazinyl,
• R 4 is hydrogen, methyl or methoxy
• R 5 is hydrogen or has one of the meanings of Ac, preferably hydrogen or acetyl,
• Y has one of the above defined meanings, preferably Vinyl, or ⁇ -sulfatoethyl.
• the black dyestuff composition may contain up to 6% of each of the red monoazo dyestuffs of the formula (5a) or (5b), or a mixture of both,
• benzene ring B1 has the same meaning as defined under formula (1 ) and Y has one of the above meanings, preferably Vinyl or ⁇ -Sulfatoethyl.
• radical (3b-1 ) is one of the following radicals
• formula (3b-2) is the following radical
• formula (3b-3) is one of the following radicals
• formula (3b-4) is one of the following radicals
• radicals X in formula (3) include Cyanamino, sulfomethylamino-, 2- sulfoethylamino, N-Methyl-2-sulfoethylamino, 3-sulfopropylamino-, 2-sulfato-ethylamino-, 3-sulfato-propylamino, 2-carboxyethylamino, Carboxymethylthio-, 2-Carboxyethylthio , 2- Carboxyethyloxy-, Carboxymethyloxy-, 2-phosphatoethylamino, 2-thiosulfoethylamino, 3- phosphatopropylamino, 3-thiosulfopropylamino, Chloro, fluoro, 2-Hydroxyethylamino, 3- hydroxypropylamino, 3-carboxy-pyridinyl, 3-Carbamoyl-pyridinyl, piperidino, or
• Suitable radicals Y include Vinyl, 2-Sulfatoethyl, 2-Chloroethyl, 2-Bromoethyl, 2- acetoxyethyl, 2-Phenoxyethyl, 2-Phosphatoethyl, and 2-Thiosulfatoethyl.
• Y is preferably Vinyl or 2-Sulfatoethyl.
• radicals -DiS0 2 Y, -D 2 S0 2 Y, -Di ' S0 2 Y and -D 2 S0 2 Y in the formulae (2) and (3) are 4-(2 ' -Sulfatoethylsulfonyl)phenyl-,
• preferred radicals -D 1 S0 2 Y and -D 1 ' S0 2 Y are 4-(2 ' -Sulfatoethylsulfonyl) phenyl- and 2-Sulfo-4-(2 ' -Sulfatoethylsulfonyl) phenyl-.
• preferred radicals -D 2 S0 2 Y, and -D 2 S0 2 Y are
• the reactive group ⁇ -Sulfatoethylsulfonyl is drawn in the form of its sulfuric acid form but can likewise be the alkali metal salt thereof, especially sodium salt, or it can be in the form of vinylsulfonyl to which it is easily converted upon exposure to alkaline medium, and the sulfo groups are drawn in the form of its sulfuric acid form as well, but can likewise be the alkali metal salt thereof, especially sodium salt.
• This illustration form is used in all further structures drawn of preferred embodiments or preferred radicals.
• the benzene radicals B1 and B2 include 1 ,4-Phenylen, 2-Sulfo-1 ,4-Phenylen, 2-Carboxy-1 ,4-Phenylen, 2, 5-dimethoxy-1 ,4-Phenylen, 2-Methoxy- 5-methyl-1 ,4-Phenylen 2-Methoxy-1 ,4-Phenylen, 2-Chloro-1 ,4-Phenylen, 2-Bromo-1 ,4- Phenylen, 1 ,3-Phenylen, 2-Methoxy-1 ,5-phenylen and 2-Sulfo-1 ,5-phenylen of which the radicals 1 ,4-Phenylen, 2-Sulfo-1 ,4-Phenylen and 2, 5-dimethoxy-1 ,4-Phenylen are especially preferred.
• Preferred dyestuffs of the formula (1 ) are:
• Y is Vinyl or ⁇ -Sulfatoethyl, and two Y substituents can have identical or different meaning, and in particular, the dyestuff is of the formula
• Y is Vinyl or ⁇ -Sultatoethyl
• the benzene radical B1 includes 1 ,4-Phenylen, 2-Sulfo-1 ,4-Phenylen, 2-Carboxy-1 ,4- Phenylen, 2, 5-dimethoxy-1 ,4-Phenylen, 2-Methoxy-5-methyl-1 ,4-Phenylen 2-Methoxy-1 ,4- Phenylen, 2-Chloro-1 ,4-Phenylen, 2-Bromo-1 ,4-Phenylen, 1 ,3-Phenylen, 2-Methoxy-1 ,5- phenylen, and 2-Sulfo-1 ,5-phenylen of which the radicals 1 ,4-Phenylen and 2-Sulfo-1 ,4- Phenylen are especially preferred.
• Preferred dyes of the formula (2) are:
• the benzene ring B3 carries 0-2 substituents methyl, methoxy or sulfo.
• the dyestuff of the formula (2a) may be particularly selected from
• R1 ' is hydrogen Sulfomethyl, Carboxymethyl, ⁇ -Carboxyethyl, or ⁇ -Sulfoethyl and R2 ' is hydrogen, methyl or methoxy.
• Y is Vinyl or ⁇ -Sulfatoethyl and two Y substituents can have identical or different meanings
• Dyestuff of the present invention may contain two dyes of the formula (2), in total 5-20%, and the two dyes being of the formula (2a°) and (2a 1 ), within the range of (2a°) : (2a 1 ) of 10:90 to 50:50, and the sum of (2a°) and (2a 1 ) being 100%
• R1 ' is Sulfomethyl, Carboxymethyl, ⁇ -Carboxyethyl, or ⁇ -Sulfoethyl
• Y is Vinyl or ⁇ -Sulfatoethyl, and the benzene ring B3 has one of the above defined meanings.
• dyestuffs of the formula (3) the following dyestuffs are preferred:
• Preferred dyes of the formula (4-2) are:
• Preferred dyes of the formula (4-3) are Preferred dyes of the formula (4-4) are
• Preferred dyes of the formula (4-5) are:
• Preferred dyestuffs of formula (5a) and (5b) are Preferred binary black dyestuff compositions according to the present invention are compositions containing 60-80% of one dye of the formula (1 ) and 20-40% of a dyestuff of the formula (3), but not containing any dyestuffs of the formula (2).
• dyestuff compositions wherein R1 ' in formula (2a) is ⁇ -Sulfoethyl or ⁇ - Carboxyethyl.
• the dyestuffs used in the mixtures of the present invention 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 their sodium, potassium or lithium salts.
• the dyestuffs are preferably used in the form of their alkali metal salts for dyeing and printing fibre materials.
• the dyestuff mixtures of the present invention can be mixed physically by mixing the respective components as dry powder in a blender, or, by mixing aqueous solutions thereof, or, in case of identical diazo components, by one pot synthesis of coupling the respective diazonium components Y0 2 S-DrN 2 + and/or Y0 2 S-D 2 -N 2 + made from aromatic amines of the formula Y0 2 S-D NH 2 and/or Y0 2 S-D 2 -NH 2 onto a mixture of the respective coupling components of the formulae.
• the present invention further provides a process for dyeing from an aqueous bath and printing of fibre materials with the dyestuff mixtures of the present invention.
• Cellulose natural cellulose fibres such as cotton, linen or hemp, especially cotton, and regenerated cellulose such as viscose or Lyocell, polyamide fibres such as nylon 6, nylon 6.6 or protein fibres such as wool or silk are preferred fibre materials.
• the inventors have arrived at the conclusion that these dyestuff mixtures are also suitable for dyeing and printing of fibre blends containing the mentioned cellulose, polyamide or protein fibre materials. Moreover, it was also found that the dyestuff mixtures of the invention can be applied to and fixed on the fibre material in various ways, in particular in the form of aqueous dye solutions and print pastes.
• the dyeing and prints are rinsed and thoroughly washed with cold or hot water, preferably at 60-98 °C, containing auxiliary agents such as detergents or surfactants that promote the wash-off of unfixed portions.
• alkali used for fixation examples include alkali hydroxide, alkali carbonate, alkali silicate, of which sodium hydroxide, sodium carbonate, sodium silicate are in particular preferred.
• the amounts wherein the dyes are applied in the dye baths can vary according to the desired depth of shade, generally amounts of 1 % to 12 % per weight of fabric are suitable, preferably 3% to 1 1 %, and in particular 5% to 10% for achieving deep black shades.
• the dye bath may contain additions of auxiliaries such as inorganic salt, preferably sodium chloride or sodium sulfate, to support the exhaustion of the dyes onto the fibre material, and in case of padding process urea, and in case of printing applications thickening pastes such as alginate thickenings.
• auxiliaries such as inorganic salt, preferably sodium chloride or sodium sulfate
• the preferred procedure is dyeing from an aqueous batch, in presence of 20-100 g/L salt, sodium chloride or sodium sulfate, and a liquor ratio of 1 :2 to 1 :50, preferably 1 :3 to 1 :30, at a dye bath pH of 7-13, preferably 9-1 1 , and a temperature of 40-90, preferably 45-70°C.
• the dyeing obtained with the dyes of the present invention has excellent fixation yield and excellent build-up.
• the obtained dye-fibre bond is of high stability not only in the acid but also in the alkaline range, also good light fastness and very good wash fastness, even in deep shades, as well as good contact fastness to water, and good acid as well as alkaline perspiration fastness.
• the dyeing obtained with the dyes of the present invention is dischargeable and can be applied in discharge printing.
• Example 1 Binary black composition containing 75% Navyblue 1 and 25% Orange 1
• the resulting dye mixture according to the invention when employed according to the application and fixation methods customary in the art for fibre reactive dyes, produces for example on cellulose fibre material such as cotton dyeings and prints in deep black shades high colour depth.
• Example 13 Black composition containing 65% Navyblue 1 , 15% Yellow 3 and 20% Orange 3
• the resulting dye mixture according to the invention when employed according to the application and fixation methods customary in the art for fibre reactive dyes, produces for example on cellulose fibre material such as cotton dyeings and prints in deep black shades high colour depth.
• Example 14 Black composition containing 67% Navyblue 1 , 18% Yellow 4 and 15% Redbrown 1
• the solution is buffered to pH 6-6.5 using a phosphate buffer and spry dried in the usual manner or standardized as a liquid formulation.
• the resulting dye mixture according to the invention when employed according to the application and fixation methods customary in the art for fibre reactive dyes, produces for example on cellulose fibre material such as cotton dyeings and prints.
• Example 15 Black composition containing 66% Navyblue 1 , 17% Yellow 5 and 17% Redbrown 1
• the first coupling is carried out at a pH value of 1 -1.5 and a temperature of 0-10 °C.
• the pH value during coupling is then slowly raised to pH 6.5 by adding small portions of soda ash 20% solution.
• the reaction mass is spry dried.
• a black composition containing 66% Navyblue 1 , 17% Yellow 5 and 17% Redbrown 1 is obtained wherein Navyblue 1 and Redbrown 1 are of the above composition and Yellow 5 is of the following structure
• the resulting dye mixture according to the invention when employed according to the application and fixation methods customary in the art for fibre reactive dyes, produces for example on cellulose fibre material such as cotton dyeings and prints.
• the dyestuffs Navybluel , Redbrownl , Orange 1 -3, Yellow 1 -5 are as de ned above.
• the following additional dyestuffs are used in the table examples
• Example 46 Black composition of 45% Navyblue 1 , 20% Navyblue 2, 20% Yellow 5 and 15% Redbrown 2
• the resulting dye mixture according to the invention when employed according to the application and fixation methods customary in the art for fibre reactive dyes, produces for example on cellulose fibre material such as cotton dyeings and prints in deep black shades high colour depth.
• A 70% of nayblue 1 , 15% Orange 9, 15% Rubine 1 (according to WO2004/069937, example 88) in 5% depth of weight of fabric.
• 100 parts per weight of cotton fabric is introduced at a temperature of 60 °C into a dyebath containing 800 parts of water, 50 parts per weight of sodium chloride, and 5 parts per weight of the dyestuff composition of example 7. After 30 min at 60 °C, 15 parts per weight of sodium carbonate is added, and the dyeing temperature is maintained at 60 °C for another 45 min.
• the dyed fabric is then rinsed in a fresh bath of 2000 parts warm water, neutralized by adding 1 part per weight of acetic acid, and soaped in another fresh bath of 2000 parts of water in presence of a conventional detergent for 5 min. at 95 °C, and dried.
• 100 parts per weight of cotton fabric is introduced at a temperature of 60 °C into a dyebath containing 1000 parts of water, 80 parts per weight of sodium chloride, and 7.5 parts per weight of the dyestuff composition of example8. After 30 min at 60 °C, 10 parts per weight of sodium carbonate is added, the dyeing temperature is maintained at 60 °C for 15 min, then 5 ml of sodium hydroxide solution is added, then dyeing temperature is maintained at 60 °C for another 30 min. The dyed fabric is then rinsed and soaped in the same manner as outlined in dyeing example 1 .
• 100 parts per weight of cotton fabric is padded with a padding liquor, applying a liquor pickup of 70% per weight of fabric, in a freshly prepared padding liquor containing 1000 parts of water, 100 parts per weight of the dyestuff mixture of composition as in example 9, 30 parts per weight of sodium carbonate and 10 parts per weight of sodium hydroxide 50% solution.
• the padded fabric is then rolled, covered to keep it wet, and stored for a period of 16 to 24 h. Finally the fabric is rinsed and soaped in the same manner as outlined in dyeing example 1 .

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