EP1173522A1 - Melanges de colorants marine fonce a base de colorants azoides reagissant avec des fibres, procede de preparation de ces melanges et technique de teintage de fibres contenant un hydroxy et/ou un carboxamido - Google Patents

Melanges de colorants marine fonce a base de colorants azoides reagissant avec des fibres, procede de preparation de ces melanges et technique de teintage de fibres contenant un hydroxy et/ou un carboxamido

Info

Publication number
EP1173522A1
EP1173522A1 EP00922621A EP00922621A EP1173522A1 EP 1173522 A1 EP1173522 A1 EP 1173522A1 EP 00922621 A EP00922621 A EP 00922621A EP 00922621 A EP00922621 A EP 00922621A EP 1173522 A1 EP1173522 A1 EP 1173522A1
Authority
EP
European Patent Office
Prior art keywords
dye
formula
hydrogen
dyes
sulfo
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP00922621A
Other languages
German (de)
English (en)
Inventor
Ronald Pedemonte
Andreas Stroben
Doriano Del Buono
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dystar Textilfarben GmbH and Co Deutschland KG
Original Assignee
Dystar Textilfarben GmbH and Co Deutschland KG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dystar Textilfarben GmbH and Co Deutschland KG filed Critical Dystar Textilfarben GmbH and Co Deutschland KG
Publication of EP1173522A1 publication Critical patent/EP1173522A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C09B67/0047—Mixtures of two or more reactive azo dyes
    • 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

Definitions

  • the present invention relates to the field of fiber-reactive dyes.
  • the present invention discloses dye mixtures comprising one or more, such as one, two or three, disazo dyes conforming to the general formula (1 )
  • R 1 is hydrogen, methyl, ethyl, methoxy, ethoxy, sulfo or carboxy, preferably methoxy or hydrogen and in particular hydrogen;
  • R is hydrogen, methyl, ethyl, methoxy, ethoxy, sulfo or carboxy, preferably hydrogen;
  • R has one of the meanings of R1 R I 4 is hydrogen, methyl, ethyl, methoxy, ethoxy, sulfo or carboxy, preferably hydrogen;
  • R 5 is hydrogen, methyl, ethyl, methoxy, ethoxy, sulfo or carboxy, preferably methoxy, sulfo or hydrogen and in particular sulfo;
  • R 6 is hydrogen, methyl, ethyl, methoxy, ethoxy, sulfo or carboxy, preferably methoxy, sulfo or hydrogen and in particular sulfo;
  • D is a benzene or naphthalene radical; n is 0 or 1 X 1 is a fluoro, chloro, cyanamido, or morpholino group or a group of the following formulae; NR 7 R 8 or OR 9 or wherein
  • R 7 is hydrogen, methyl, ethyl, hydroxyethyl, methoxyethyl, ethoxyethyl, or sulfoethyl, preferably ethyl, methoxyethyl, sulfoethyl R 8 has one of the meanings of R 7 ;
  • R 9 has one of the meanings of R 7 ;
  • R 10 has one of the meanings of R 7 ;
  • R 1 is hydrogen, methyl, ethyl, methoxy, ethoxy, sulfo or carboxy, preferably methoxy or hydrogen and in particular hydrogen;
  • R 12 is hydrogen, methyl, ethyl, methoxy, ethoxy, sulfo or carboxy, preferably methoxy or hydrogen and in particular hydrogen;
  • X 2 has one of the meanings of X ;
  • Y 1 is vinyl, or is ethyl substituted in the ⁇ -position by a substituent which is eliminated by the action of an alkali, forming the vinyl group, such as chlorine, thiosulfato, sulfato, alkanoyloxy of 2 to 5 carbon atoms, such as acetyloxy, phosphato, sulfobenzoyloxy and p-toluylsulfonyloxy, and Y 1 is preferably vinyl, ⁇ -chloroethyl, ⁇ -thiosulfatoethyl or ⁇ -sulfatoethyl and is in particular preferably vinyl or ⁇ -sulfatoethyl; Y 2 has one of the meanings of Y 1 ;
  • Y 3 has one of the meanings of Y 1 ;
  • Y 4 has one of the meanings of Y 1 ;
  • M denotes hydrogen or an alkali metal such as lithium, sodium and potassium.
  • sulfo are groups of the formula -SO 3 M
  • thiosulfato groups are groups of the formula -S-S0 3 M
  • carboxy groups are groups of the formula -COOM
  • phosphato groups are groups of the formula -OPO 3 M 2
  • sulfato groups are groups of the formula -OSO 3 M , in which M is defined as above.
  • the dye, respectively dyes, of the general formula (1 ) are present in the mixtures in an amount of from 70 to 95% by weight, preferably of from 75 to 90 % by weight, and the dye, respectively dyes of the general formula (2) are present in the mixtures in an amount of from 5 to 30% by weight, preferably of from 10 to 25 % by weight.
  • the dye mixtures of the invention may optionally contain one, two or three dyestuffs corresponding to the general formula (3a) or (3b) or both
  • R 1 , R 2 , R 3 , R 4 , M, Y 1 and Y 2 are defined as above.
  • These two monoazo dyestuffs may be already formed during the synthesis of the disazo dye of formula (1 ) when coupling reactions of the starting compounds are incomplete.
  • the dye mixture of the instant invention contains, as a further component, a monoazo dyestuff of formula (3a) or of formula (3b) or both, the dye or dyes of formula (3a) or of formula (3b) or of both are present in the dye mixture of the dyes of formula (1 ) and (2) in the range of 0.01 to 8 % by weight, calculated on the 100 % dye mixture of the dyes (1 ) and (2).
  • the dyes of the general formulae (1 ), (2), (3a) and (3b), in particular if those corresponding to the same general formula have the same chromophore, can have, within the meaning of their Y-moiety, structurally different fiber-reactive groups corresponding to their -SO 2 - Y-moiety.
  • the dye mixture can contain dyes of the same chromophore conforming to the formula (1) and/or dyes of the same chromophore conforming to formula (2), optionally likewise of the general formula (3a) or (3b) or both in which the fiber-reactive groups of the corresponding -S0 2 -Y-moiety are partly vinylsulfonyl groups and partly groups in which the Y-moiety is a ⁇ -ethyl substituted group as defined above, such as ⁇ -chloroethylsufonyl, ⁇ -thiosulfatoethylsulfonyl or, preferably, ⁇ -sulfatoethylsulfonyl groups.
  • the proportion of the respective vinylsulfonyl dye to the respective dye with a Y-moiety being a ⁇ -ethyl substituted group as defined above, such as a ⁇ - chloro- or ⁇ -thiosulfato- or ⁇ -sulfatoethyl-sulfonyl dye, will be up to about 30 mol-%, based on the respective dye chromophore.
  • (3a) and (3b) are, for example, 2-( ⁇ -sulfatoethylsulfonyl)phenyl, 3-( ⁇ -sulfatoethylsulfonyl)phenyl, 3- or 4-vinylsulfonylphenyl, 4-( ⁇ -sulfatoethylsulfonyl)phenyl, 2-carboxy-5-( ⁇ - sulfatoethylsulfonyl)phenyl, 4-methoxy-3-( ⁇ -sulfatoethylsulfonyl)-phenyl, 2-ethoxy-4- or -5-( ⁇ -sulfatoethylsulfonyl)phenyl, 2-methyl-4-( ⁇ -sulfatoethylsulfonyl)- phenyl, 2-methoxy-5- or -4-( ⁇ -sulfatoethylsulfonylsulfulfonyl)phenyl
  • D is the radical of 1 ,5-disulfonaphthyl
  • R 1 is methoxy or hydrogen
  • R 2 is hydrogen
  • R 3 is methoxy or hydrogen
  • R 4 is hydrogen
  • X 1 is chlorine
  • X 2 is the radical 4-( ⁇ -sulfatoethylsulfonyl)phenyl and R 1 , R 2 , R 3 and R 4 are in particular preferred each hydrogen and the Y-moieties are each preferable, independently of the other one vinyl or ⁇ -sulfatoethyl.
  • the dye mixtures of the invention can be present as a preparation in solid or liquid (dissolved) form.
  • solid form they generally contain the electrolyte salts customary in the case of water-soluble and in particular fiber-reactive dyes, such as sodium chloride, potassium chloride and sodium sulfate, and also the assistants customary in commercial dyes, such as buffer substances capable of establishing a pH in aqueous solution between 3 and 7, such as sodium acetate, sodium borate, sodium bicarbonate, sodium dihydrogenphosphate and disodium hydrogenphosphate, small amounts of siccatives or, if they are present in liquid, aqueous solution (including the presence of thickeners of the type customary in print pastes), substances which ensure the permanence of these preparations, for example mold preventatives.
  • buffer substances capable of establishing a pH in aqueous solution between 3 and 7, such as sodium acetate, sodium borate, sodium bicarbonate, sodium dihydrogenphosphate and disodium hydrogenphosphate, small amounts of siccatives or,
  • the dye mixtures take the form of dye powders, they contain, as a rule, 10 to 80 % by weight, based on the dye powder or preparation, of a strength-standardizing colorless diluent electrolyte salt, such as those mentioned above. These dye powders may in addition contain the abovementioned buffer substances in a total amount of up to 5 %, based on the dye powder.
  • the total dye content of these aqueous solutions is up to about 50 % by weight, the electrolyte salt content of these aqueous solutions preferably being below 10 % by weight, based on the aqueous solutions (liquid preparations) can in general contain the abovementioned buffer substances in an amount of up to 5 % by weight, preferably up to 2 % by weight.
  • the dye mixtures of the invention are preparable in a conventional manner, as by mechanically mixing the individual dyes in the necessary proportions, whether in the form of their dye powders or granules or their synthesis solution or of aqueous solutions of the individual dyes in general, which may still include customary auxiliaries.
  • the dyes according to the general formula (1 ) are known from the U.S. Patents Nos. 2,657,205, 3,387,914, 4,072,463 and 4,257,770 or from one of the above- mentioned publications, and the dyes of the general formula (2) are known from the European Patent Application EP-A 534 342 and from the European Patent Application EP A 177 449.
  • the dye mixtures of the instant invention are well suitable for dyeing (which includes printing) hydroxy- and/or carboxamido-containing fiber materials by the application and fixing methods numerously described in the art for fiber-reactive dyes, in deep navy shades with good color build-up and good wash-off in respect of unfixed dye portions.
  • the present invention therefore also provides for use of the novel dye mixtures for dyeing (including printing) hydroxy- and/or carboxamido-containing fiber materials and processes for dyeing such fiber materials and processes for dyeing such materials using a dye mixture according to the invention by applying the dye mixture to the substrate in dissolved form and fixing the dyes on the fiber by the action of an alkali or by heating or both.
  • Hydroxy-containing materials are natural or synthetic hydroxy-containing materials, for example cellulose fiber materials, including in the form of paper, or their regenerated products and polyvinyl alcohols.
  • Cellulose fiber materials are preferably cotton but also other natural vegetable fibers, such as linen, hemp, jute and ramie fibers; regenerated cellulose fibers are for example staple viscose and filament viscose.
  • Carboxamido-containing materials are for example synthetic and natural polyamides and polyurethanes, in particular in the form of fibers, for example wool and other animal hairs, silk, leather, nylon-6,6, nylon-6, nylon-11 , and nylon-4.
  • the dye mixtures of the invention can also be used for the fiber-reactive dyeing of wool.
  • wool which has been given a nonfelting or low-felting finish cf. H. Rath, Lehrbuch der Textilchemie, Springer-Verlag, 3rd Edition (1972), p. 295-299, especially the finish by the so-called Hercosett process (p. 298); J. Soc. Dyers and Colourists 1972, 93-99, and 1975, 33-44) can be dyed with very good fastness properties.
  • the process of dyeing on wool is here carried out in a conventional manner from an acidic medium.
  • acetic acid and/or ammonium sulfate or acetic acid and ammonium acetate or sodium acetate may be added to the dyebath to obtain the desired pH.
  • a customary leveling agent for example on the basis of a reaction product of cyanuric chloride with 3 times the molar amount of an aminobenzenesulfonic acid and/or of an aminonaphthalenesulfonic acid or on the basis of a reaction product of for example stearylamine with ethylene oxide.
  • the dye mixture of the invention is preferably subjected to the exhaustion process initially from an acidic dyebath having a pH of about 3.5 to 5.5 under pH control and the pH is then, toward the end of the dyeing time, shifted into the neutral and perhaps weakly alkaline range up to a pH of 8.5 to bring about, especially for very deep dyeings, the full reactive bond between the dyes of the dye mixtures of the invention and the fiber. At the same time, the dye portion not reactively bound is removed.
  • the procedure described herein also applies to the production of dyeings on fiber materials composed of other natural polyamides or of synthetic polyamides and polyurethanes.
  • the material to be dyed is introduced into the bath at a temperature of about 40°C, agitated therein for some time, the dyebath is then adjusted to the desired weakly acidic, preferably weakly acetic acid, pH and the actual dyeing is carried out at a temperature between 60 and 98°C.
  • the dyeings can also be carried out at the boil or in sealed dyeing apparatus at temperatures of up to 106°C. Since the water solubility of the dye mixtures of the invention is very good, they can also be used with advantage in customary continuous dyeing processes.
  • the color strength of the dye mixtures of the invention is very high.
  • the dye mixtures of the invention is by generally known processes for dyeing and printing fiber materials by the known application techniques for fiber- reactive dyes. Since the dyes of the dye mixtures according to the invention are highly compatible with one another, the dye mixtures of the invention are also advantageously useful in exhaust dyeing processes. Applied in this way for example to cellulose fibers from a long liquor ratio at temperatures between 40 and 105°C, optionally at temperatures up to 130°C, under superatmosphe c pressure, and optionally in the presence of customary dyeing assistants with the use of acid- binding agents and optionally neutral salts, such as sodium chloride or sodium sulfate, they produce dyeings in very good color yields with excellent color build-up and consistent shade.
  • One possible procedure is to introduce the material into the warm bath, gradually heat the bath to the desired dyeing temperature, and complete the dyeing process at that temperature.
  • the neutral salts which speed up the exhaustion of the dyes can also if desired not be added to the bath until the actual dyeing temperature has been reached.
  • the conventional printing processes for cellulose fibers which can either be carried out in single-phase, for example by printing with a print paste containing sodium bicarbonate or some other acid-binding agent and the colorant, and subsequent steaming at from 100 to 103°C, or in two phases, for example by printing with a neutral or weakly acid print paste containing the colorant and subsequent fixation either by passing the printed material through a hot electrolyte-containing alkaline bath or by overpadding with an alkaline electrolyte-containing padding liquour and subsequent batching of this treated material or subsequent steaming or subsequent treatment with dry heat, produce strong prints with well defined contours and a clear white ground. Changing fixing conditions has only little effect on the outcome of the prints.
  • the hot air used in dry heat fixing by the customary thermofix processes has a temperature of from 120 to 200°C.
  • the customary steam at from 101 to 103°C, it is also possible to use superheated steam and high pressure steam at up to 160°C.
  • Acid-binding agents responsible for fixing the dyes to cellulose fibers are for example water-soluble basic salts of alkali metals and of alkaline earth metals of inorganic or organic acids, and compounds which release alkali when hot.
  • alkali metal hydroxides and alkali metal salts of weak to medium inorganic or organic acids the preferred alkali metal compounds being the sodium and potassium compounds.
  • These acid-binding agents are for example sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, sodium formate, sodium dihydrogenphosphate and disodium hydrogenphosphate.
  • the dyeings of polyurethane and polyamide fibers are customarily carried out from an acid medium.
  • the dyebath may contain for example acetic acid and/or ammonium sulfate and/or acetic acid and ammonium acetate or sodium acetate to bring it to the desired pH.
  • the material to be dyed is introduced into the bath at a temperature of about 40°C and agitated therein for some time, the dyebath is then adjusted to the desired weakly acid, preferably weakly acetic acid, pH, and the actual dyeing is carried out at temperature between 60 and 98°C.
  • the dyeings can also be carried out at the boil or at temperatures up to 120°C (under superatmospheric pressure).
  • a dye mixture according to the invention is prepared by mechanically mixing 150 parts of a navy-blue electrolyte-salt containing powder with a content of 50% of a dye of formula (A)
  • the resulting mixture contains 75% (w/w) of dye (A) and 20% (w/w) of dye (B) and 5% (w/w) of dye (C) and dyes wool in navy-blue shades.
  • the dye mixture exhibits excellent dyestuff properties (i.e. lightfastness and washfastness).
  • a dye mixture according to the invention is prepared by mechanically mixing 155 parts of a navy-blue electrolyte-salt containing powder with a content of 50% of a dye of formula (A) with 33.3 parts of a red electrolyte-salt containing powder with a content of 60% of a dye of formula (B) with 5.0 parts of a red electrolyte-salt containing powder with a content of 50% of a dye of formula (C).
  • the resulting mixture contains 77.5% (w/w) of dye (A) and 20% (w/w) of dye (B) and 2.5% (w/w) of dye (C) and dyes wool in navy-blue shades.
  • the dye mixture exhibits excellent dyestuff properties (i.e. lightfastness and washfastness).
  • a dye mixture according to the invention is prepared by mechanically mixing 160 parts of a navy-blue electrolyte-salt containing powder with a content of 50% of a dye of formula (A) with 25 parts of a red electrolyte-salt containing powder with a content of 60% of a dye of formula (B) with 10.0 parts of a red electrolyte-salt containing powder with a content of 50% of a dye of formula (C).
  • the resulting mixture contains 80% (w/w) of dye (A) and 15% (w/w) of dye (B) and 5% (w/w) of dye (C) and dyes wool in navy-blue shades.
  • the dye mixture exhibits excellent dyestuff properties (i.e. lightfastness and washfastness).
  • a dye mixture according to the invention is prepared by mechanically mixing 170 parts of a navy-blue electrolyte-salt containing powder with a content of 50% of a dye of formula (A) with 16.6 parts of a red electrolyte-salt containing powder with a content of 60% of a dye of formula (B) with 10.0 parts of a red electrolyte-salt containing powder with a content of 50% of a dye of formula (C).
  • the resulting mixture contains 85% (w/w) of dye (A) and 10% (w/w) of dye (B) and 5% (w/w) of dye (C) and dyes wool in navy-blue shades.
  • the dye mixture exhibits excellent dyestuff properties (i.e. lightfastness and washfastness).
  • a dye mixture according to the invention is prepared by mechanically mixing 150 parts of a navy-blue electrolyte-salt containing powder with a content of 50% of a dye of formula (A) with 16.6 parts of a red electrolyte-salt containing powder with a content of 60% of a dye of formula (B) with 10.0 parts of a red electrolyte-salt containing powder with a content of 50% of a dye of formula (C) with 20.0 parts of a red electrolyte-salt containing powder with a content of 50% of a dye of formula (D).
  • the resulting mixture contains 75% (w/w) of dye (A) and 10% (w/w) of dye (B) and 5% (w/w) of dye (C) and 10% (w/w) of dye (D) and dyes wool in navy-blue shades.
  • the dye mixture exhibits excellent dyestuff properties (i.e. lightfastness and washfastness).
  • a dye mixture according to the invention is prepared by mechanically mixing 160 parts of a navy-blue electrolyte-salt containing powder with a content of 50% of a dye of formula (A) with 16.6 parts of a red electrolyte-salt containing powder with a content of 60% of a dye of formula (B) and with 20.0 parts of a red electrolyte-salt containing powder with a content of 50% of a dye of formula (D).
  • the resulting mixture contains 80% (w/w) of dye (A) and 10% (w/w) of dye (B) and 10% (w/w) of dye (D) and dyes wool in navy-blue shades.
  • the dye mixture exhibits excellent dyestuff properties (i.e. lightfastness and washfastness).
  • a dye mixture according to the invention is prepared by mechanically mixing 150 parts of a navy-blue electrolyte-salt containing powder with a content of 50% of a dye of formula (A) with 28.5 parts of a red electrolyte-salt containing powder with a content of 70% of a dye of formula (E) and with 10.0 parts of a red electrolyte-salt containing powder with a content of 50% of a dye of formula (C).
  • the resulting mixture contains 75% (w/w) of dye (A) and 20% (w/w) of dye (E) and 5% (w/w) of dye (C) and dyes wool in navy-blue shades.
  • the dye mixture exhibits excellent dyestuff properties (i.e. lightfastness and washfastness).
  • a dye mixture according to the invention is prepared by mechanically mixing 160 parts of a navy-blue electrolyte-salt containing powder with a content of 50% of a dye of formula (A) with 21.5 parts of a red electrolyte-salt containing powder with a content of 70% of a dye of formula (E) and with 10.0 parts of a red electrolyte-salt containing powder with a content of 50% of a dye of formula (C).
  • the resulting mixture contains 80% (w/w) of dye (A) and 15% (w/w) of dye (E) and 5% (w/w) of dye (C) and dyes wool in navy-blue shades.
  • the dye mixture exhibits excellent dyestuff properties (i.e. lightfastness and washfastness).
  • a dye mixture according to the invention is prepared by mechanically mixing 160 parts of a navy-blue electrolyte-salt containing powder with a content of 50% of a dye of formula (A) with 23 parts of a red electrolyte-salt containing powder with a content of 65% of a dye of formula (F) and with 10.0 parts of a red electrolyte-salt containing powder with a content of 50% of a dye of formula (C).
  • the resulting mixture contains 80% (w/w) of dye (A) and 15% (w/w) of dye (F) and 5% (w/w) of dye (C) and dyes wool in navy-blue shades.
  • the dye mixture exhibits excellent dyestuff properties (i.e. lightfastness and washfastness).
  • a dye mixture according to the invention is prepared by mechanically mixing 170 parts of a navy-blue electrolyte-salt containing powder with a content of 50% of a dye of formula (A) with 23 parts of a red electrolyte-salt containing powder with a content of 65% of a dye of formula (F).
  • the resulting mixture contains 85% (w/w) of dye (A) and 15% (w/w) of dye (F) and dyes wool in navy-blue shades.
  • the dye mixture exhibits excellent dyestuff properties (i.e. lightfastness and washfastness).
  • a dye mixture according to the invention is prepared by mechanically mixing 150 parts of a navy-blue electrolyte-salt containing powder with a content of 50% of a dye of formula (A) with 30.7 parts of a red electrolyte-salt containing powder with a content of 65% of a dye of formula (G) and with 10.0 parts of a red electrolyte-salt containing powder with a content of 50% of a dye of formula (C).
  • the resulting mixture contains 75% (w/w) of dye (A) and 20% (w/w) of dye (G) and 5% (w/w) of dye (C) and dyes wool in navy-blue shades.
  • the dye mixture exhibits excellent dyestuff properties (i.e. lightfastness and washfastness).
  • a dye mixture according to the invention is prepared by mechanically mixing 160 parts of a navy-blue electrolyte-salt containing powder with a content of 50% of a dye of formula (A) with 23 parts of a red electrolyte-salt containing powder with a content of 65% of a dye of formula (G) and with 10.0 parts of a red electrolyte-salt containing powder with a content of 50% of a dye of formula (C).
  • the resulting mixture contains 80% (w/w) of dye (A) and 15% (w/w) of dye (G) and 5% (w/w) of dye (C) and dyes wool in navy-blue shades.
  • the dye mixture exhibits excellent dyestuff properties (i.e. lightfastness and washfastness).
  • a dye mixture according to the invention is prepared by mechanically mixing 160 parts of a navy-blue electrolyte-salt containing powder with a content of 50% of a dye of formula (A) with 30 parts of a red electrolyte-salt containing powder with a content of 50% of a dye of formula (H) and with 10.0 parts of a red electrolyte-salt containing powder with a content of 50% of a dye of formula (C).
  • the resulting mixture contains 80% (w/w) of dye (A) and 15% (w/w) of dye (H) and 5% (w/w) of dye (C) and dyes wool in navy-blue shades.
  • the dye mixture exhibits excellent dyestuff properties (i.e. lightfastness and washfastness).
  • a dye mixture according to the invention is prepared by mechanically mixing 160 parts of a navy-blue electrolyte-salt containing powder with a content of 50% of a dye of formula (A) with 30 parts of a red electrolyte-salt containing powder with a content of 50% of a dye of formula (I) and with 10.0 parts of a red electrolyte-salt containing powder with a content of 50% of a dye of formula (C).
  • the resulting mixture contains 80% (w/w) of dye (A) and 15% (w/w) of dye (I) and 5% (w/w) of dye (C) and dyes wool in navy-blue shades.
  • the dye mixture exhibits excellent dyestuff properties (i.e. lightfastness and washfastness).
  • a dye mixture according to the invention is prepared by mechanically mixing 160 parts of a navy-blue electrolyte-salt containing powder with a content of 50% of a dye of formula (A) with 30 parts of a red electrolyte-salt containing powder with a content of 50% of a dye of formula (J) and with 10.0 parts of a red electrolyte-salt containing powder with a content of 50% of a dye of formula (C).
  • the resulting mixture contains 80% (w/w) of dye (A) and 15% (w/w) of dye (J) and 5% (w/w) of dye (C) and dyes wool in navy-blue shades.
  • the dye mixture exhibits excellent dyestuff properties (i.e. lightfastness and washfastness).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Abstract

Cette invention a trait à un mélange de colorants renfermant un ou plusieurs colorants disazoïque, en l'occurrence un, deux ou trois, correspondant à la formule générale (1) et un ou plusieurs colorants monoazoïque, en l'occurrence un, deux ou trois, correspondant à la formule générale (2). Les formules (1) et (2) sont telles que définies dans la première revendication. L'invention concerne également un procédé de préparation de ce mélange ainsi qu'une technique de teintage de matériau fibreux contenant un hydroxy et/ou un carboxamido, laquelle technique utilise le colorant selon l'invention.
EP00922621A 1999-04-15 2000-04-08 Melanges de colorants marine fonce a base de colorants azoides reagissant avec des fibres, procede de preparation de ces melanges et technique de teintage de fibres contenant un hydroxy et/ou un carboxamido Withdrawn EP1173522A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US29196199A 1999-04-15 1999-04-15
US291961 1999-04-15
PCT/EP2000/003150 WO2000063298A1 (fr) 1999-04-15 2000-04-08 Melanges de colorants marine fonce a base de colorants azoides reagissant avec des fibres, procede de preparation de ces melanges et technique de teintage de fibres contenant un hydroxy et/ou un carboxamido

Publications (1)

Publication Number Publication Date
EP1173522A1 true EP1173522A1 (fr) 2002-01-23

Family

ID=23122603

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00922621A Withdrawn EP1173522A1 (fr) 1999-04-15 2000-04-08 Melanges de colorants marine fonce a base de colorants azoides reagissant avec des fibres, procede de preparation de ces melanges et technique de teintage de fibres contenant un hydroxy et/ou un carboxamido

Country Status (10)

Country Link
EP (1) EP1173522A1 (fr)
JP (1) JP2002542366A (fr)
KR (1) KR20020033090A (fr)
CN (1) CN1344294A (fr)
AU (1) AU4294600A (fr)
BR (1) BR0009692A (fr)
CA (1) CA2370403A1 (fr)
MX (1) MXPA01010432A (fr)
TR (1) TR200102952T2 (fr)
WO (1) WO2000063298A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4639490B2 (ja) * 2001-02-20 2011-02-23 住友化学株式会社 反応染料混合物及びそれらの繊維材料への適用
JP4486810B2 (ja) * 2003-01-08 2010-06-23 富士フイルム株式会社 着色組成物及びインクジェット記録方法
EP1675915A1 (fr) * 2003-10-20 2006-07-05 Ciba SC Holding AG Melanges de colorants reactifs et leur utilisation
KR100686978B1 (ko) * 2006-04-21 2007-02-26 (주)경인양행 반응성 염료 조성물 및 이를 이용한 섬유의 염색방법

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02202956A (ja) * 1989-01-24 1990-08-13 Rika Sangyo Kk 反応性黒色染料組成物
DE4414320A1 (de) * 1994-04-25 1995-10-26 Hoechst Ag Schwarze Farbstoffmischungen von faserreaktiven Azofarbstoffen und ihre Verwendung zum Färben von hydroxy- und/oder carbonamidgruppenhaltigem Fasermaterial
DE19508156A1 (de) * 1995-03-08 1996-09-12 Hoechst Ag Schwarze Farbstoffmischungen von faserreaktiven Azofarbstoffen und ihre Verwendung zum Färben von hydroxy- und/oder carbonamidgruppenhaltigem Fasermaterial
DE19511688C2 (de) * 1995-03-30 1999-07-22 Dystar Textilfarben Gmbh & Co Farbstoffmischungen von faserreaktiven Azofarbstoffen und ihre Verwendung zum Färben von hydroxy- und/oder carbonamidgruppenhaltigem Fasermaterial
DE19635999A1 (de) * 1996-09-05 1998-03-12 Dystar Textilfarben Gmbh & Co Farbstoffmischungen von faserreaktiven Azofarbstoffen und ihre Verwendung zum Färben von hydroxy- und/oder carbonamidgruppenhaltigem Fasermaterial
JPH11335576A (ja) * 1998-05-28 1999-12-07 Sumitomo Chem Co Ltd 反応染料組成物およびそれを用いる繊維材料の染色または捺染方法
TW460545B (en) * 1998-07-21 2001-10-21 Dystar Textilfarben Gmbh & Amp Dye mixture
US6171349B1 (en) * 1999-01-20 2001-01-09 Everlight Usa, Inc. Reactive dye composition

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0063298A1 *

Also Published As

Publication number Publication date
AU4294600A (en) 2000-11-02
JP2002542366A (ja) 2002-12-10
BR0009692A (pt) 2002-01-08
WO2000063298A1 (fr) 2000-10-26
TR200102952T2 (tr) 2002-04-22
MXPA01010432A (es) 2002-03-27
KR20020033090A (ko) 2002-05-04
CA2370403A1 (fr) 2000-10-26
CN1344294A (zh) 2002-04-10

Similar Documents

Publication Publication Date Title
US5445654A (en) Black dye mixtures of fiber-reactive azo dyes and use thereof for dyeing hydroxy- and/or carboxamido-containing fiber material
EP0976792B1 (fr) Mélanges de colorants réactifs noirs
US6165231A (en) Dye mixture, process for it's preparation and use thereof
EP1035173B1 (fr) Mélanges de colorants azoiques réactifs noirs et leur utilisation pour teindre un matériau fibreux contenant des groupes hydroxyles et/ou carbonamides
US6036732A (en) Black dye mixtures of fiber-reactive azo dyes, methods for their preparation and use thereof for dyeing hydroxy-and/or carboxamido-cont
JPH1143624A (ja) 繊維反応性染料の青色染色混合物およびヒドロキシおよび／またはカルボキシアミド基を含有する繊維材料の染色にそれらを使用する方法
EP0974621B1 (fr) Mélanges bleu-marine de colorants azoiques réactifs
EP1155089B1 (fr) Melanges colorants noir-noir de colorants aux fibres azo reactifs et procede de teinture de fibres contenant des groupements hydroxy et/ou carboxamido.
US5931974A (en) Deep black dye mixtures of fiber-reactive azo dyes and use thereof for dyeing hydroxy- and/or carboxamido-containing fiber material
EP1213329B1 (fr) Mélanges de colorants noirs à base de colorants azoiques réagissant avec des fibres, leurs procédés de préparation et leur utilisation pour la teinture d'un matériau fibreux contenant un hydroxy et/ou un carboxamido
US20040049019A1 (en) Black dye mixtures of fibre-reactive azo dyes and the use thereof for dyeing fibre material containing hydroxy and/or carbonamide groups
EP1106655B1 (fr) Mélanges de colorants azoiques réactifs et leur utilisation pour teindre un matériau contenant des groupes hydroxyles et/ou carbonamides
EP0982374B1 (fr) Mélanges de colorants azoiques réactifs noirs et leur utilisation pour teindre un matériau fibreux contenant des groupes hydroxyles et/ou carbonamides
EP1305369A2 (fr) Melanges de colorants azoiques reagissant avec les fibres et leur utilisation pour colorer une matiere contenant des groupes hydroxy et/ou carboxamide
EP1090962B1 (fr) Mélanges de colorants azoiques réactifs et leur utilisation pour teindre un matériau contenant des groupes hydroxyles et/ou carbonamides
WO2000063298A1 (fr) Melanges de colorants marine fonce a base de colorants azoides reagissant avec des fibres, procede de preparation de ces melanges et technique de teintage de fibres contenant un hydroxy et/ou un carboxamido
EP1046678B1 (fr) Mélanges de colorants azoiques réactifs et leur utilisation pour teindre un matériau contenant des groupes hydroxyles et/ou carbonamides
US6358287B1 (en) Mixtures of fiber-reactive dyes, preparation thereof and use thereof for dyeing fiber materials
US6228131B1 (en) Dye mixtures comprising water-soluble fiber-reactive azo dyes, preparation thereof and use thereof
US20030229952A1 (en) Mixtures of fiber-reactive bisazo dyes and use thereof
EP1305372A2 (fr) Melanges de colorants noirs a base de colorants azoiques reagissant avec des fibres, leurs procedes de preparation et leur utilisation pour la teinture d'un materiau fibreux contenant un hydroxy et/ou un carboxamido
MXPA99008964A (en) Mixtures of water soluble reactive azo dyes, process to manufacture them and their use

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20011115

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE

AX Request for extension of the european patent

Free format text: AL;LT;LV;MK;RO;SI

17Q First examination report despatched

Effective date: 20020221

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: DYSTAR TEXTILFARBEN GMBH & CO. DEUTSCHLAND KG

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20020904

RBV Designated contracting states (corrected)

Designated state(s): CH DE FR GB IT LI PT