WO2000063298A1 - Deep navy dye mixtures of fiber-reactive azo dyes and a method for their preparation and a process for dyeing hydroxy and/or carboxamido containing fibers - Google Patents
Deep navy dye mixtures of fiber-reactive azo dyes and a method for their preparation and a process for dyeing hydroxy and/or carboxamido containing fibers Download PDFInfo
- Publication number
- WO2000063298A1 WO2000063298A1 PCT/EP2000/003150 EP0003150W WO0063298A1 WO 2000063298 A1 WO2000063298 A1 WO 2000063298A1 EP 0003150 W EP0003150 W EP 0003150W WO 0063298 A1 WO0063298 A1 WO 0063298A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- dye
- formula
- hydrogen
- dyes
- sulfo
- Prior art date
Links
- 0 *c(cc1)ccc1Nc1nc(NC(C2=C([C@@]3N=Nc(ccc4c5cccc4)c5S(O)(=O)=O)O)=CC(S(O)(=O)=O)=CC2=CC3S(O)(=O)=O)nc(Cl)n1 Chemical compound *c(cc1)ccc1Nc1nc(NC(C2=C([C@@]3N=Nc(ccc4c5cccc4)c5S(O)(=O)=O)O)=CC(S(O)(=O)=O)=CC2=CC3S(O)(=O)=O)nc(Cl)n1 0.000 description 2
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
- C09B67/0047—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
-
- 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
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2000612379A JP2002542366A (en) | 1999-04-15 | 2000-04-08 | Dark Navy Dye Mixture of Fiber Reactive Azo Dyes, Preparation Method Thereof and Dyeing Method for Hydroxy / Carboxamide-Containing Fibers |
MXPA01010432A MXPA01010432A (en) | 1999-04-15 | 2000-04-08 | Deep navy dye mixtures of fiber-reactive azo dyes and a method for their preparation and a process for dyeing hydroxy and/or carboxamido containing fibers. |
BR0009692-0A BR0009692A (en) | 1999-04-15 | 2000-04-08 | Mixtures of reactive azo dyes with fibers with dark navy blue dyes, and method for their preparation and process for dyeing fibers containing hydroxy and / or carboxamido |
KR1020017012980A KR20020033090A (en) | 1999-04-15 | 2000-04-08 | Deep navy dye mixtures of fiber-reactive azo dyes and a method for their preparation and a process for dyeing hydroxy and/or carboxamido containing fibers |
CA002370403A CA2370403A1 (en) | 1999-04-15 | 2000-04-08 | Deep navy dye mixtures of fiber-reactive azo dyes and a method for their preparation and a process for dyeing hydroxy and/or carboxamido containing fibers |
AU42946/00A AU4294600A (en) | 1999-04-15 | 2000-04-08 | Deep navy dye mixtures of fiber-reactive azo dyes and a method for their preparation and a process for dyeing hydroxy and/or carboxamido containing fibers |
EP00922621A EP1173522A1 (en) | 1999-04-15 | 2000-04-08 | Deep navy dye mixtures of fiber-reactive azo dyes and a method for their preparation as well as a process for dyeing hydroxy- and/or carboxamido-containing fibers |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US29196199A | 1999-04-15 | 1999-04-15 | |
US09/291,961 | 1999-04-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000063298A1 true WO2000063298A1 (en) | 2000-10-26 |
Family
ID=23122603
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2000/003150 WO2000063298A1 (en) | 1999-04-15 | 2000-04-08 | Deep navy dye mixtures of fiber-reactive azo dyes and a method for their preparation and a process for dyeing hydroxy and/or carboxamido containing fibers |
Country Status (10)
Country | Link |
---|---|
EP (1) | EP1173522A1 (en) |
JP (1) | JP2002542366A (en) |
KR (1) | KR20020033090A (en) |
CN (1) | CN1344294A (en) |
AU (1) | AU4294600A (en) |
BR (1) | BR0009692A (en) |
CA (1) | CA2370403A1 (en) |
MX (1) | MXPA01010432A (en) |
TR (1) | TR200102952T2 (en) |
WO (1) | WO2000063298A1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002241637A (en) * | 2001-02-20 | 2002-08-28 | Sumitomo Chem Co Ltd | Reactive dye mixture and application of the same to fiber material |
EP1437388A1 (en) * | 2003-01-08 | 2004-07-14 | Fuji Photo Film Co., Ltd. | Coloring composition and inkjet recording method |
WO2005040285A1 (en) * | 2003-10-20 | 2005-05-06 | Ciba Specialty Chemicals Holding Inc. | Mixtures of reactive dyes and their use |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100686978B1 (en) * | 2006-04-21 | 2007-02-26 | (주)경인양행 | Composition of reactive dyestuffs and methods for dyeing fiber using the same |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0679697A2 (en) * | 1994-04-25 | 1995-11-02 | Hoechst Aktiengesellschaft | Black mixtures of reactive azo dyes and their use for dyeing fibrous material containing hydroxy and/or carbonamide groups |
EP0731145A2 (en) * | 1995-03-08 | 1996-09-11 | Hoechst Aktiengesellschaft | Black dyestuff mixtures of fibre reactive azo dyestuffs and their utilization for dyeing of hydroxy- and/or carbonamide group containing fibre material |
EP0735112A2 (en) * | 1995-03-30 | 1996-10-02 | Hoechst Aktiengesellschaft | Mixtures of reactive azo dyes and their use for dyeing fibrous material containing hydroxy and/or carbonamide groups |
EP0827987A2 (en) * | 1996-09-05 | 1998-03-11 | DyStar Textilfarben GmbH & Co. Deutschland KG | Mixtures of azo reactive dyes and their use for dyeing fiber material containing hydroxy or carbonamide groups |
EP0974622A1 (en) * | 1998-07-21 | 2000-01-26 | DyStar Textilfarben GmbH & Co. Deutschland KG | Mixture of water soluble reactive azo dyes, process to manufacture it and its use |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02202956A (en) * | 1989-01-24 | 1990-08-13 | Rika Sangyo Kk | Reactive black dye composition |
JPH11335576A (en) * | 1998-05-28 | 1999-12-07 | Sumitomo Chem Co Ltd | Reaction dye composition and dyeing or printing method of fiber material by use thereof |
US6171349B1 (en) * | 1999-01-20 | 2001-01-09 | Everlight Usa, Inc. | Reactive dye composition |
-
2000
- 2000-04-08 WO PCT/EP2000/003150 patent/WO2000063298A1/en not_active Application Discontinuation
- 2000-04-08 CN CN00805263A patent/CN1344294A/en active Pending
- 2000-04-08 AU AU42946/00A patent/AU4294600A/en not_active Abandoned
- 2000-04-08 KR KR1020017012980A patent/KR20020033090A/en not_active Application Discontinuation
- 2000-04-08 TR TR2001/02952T patent/TR200102952T2/en unknown
- 2000-04-08 BR BR0009692-0A patent/BR0009692A/en not_active Application Discontinuation
- 2000-04-08 EP EP00922621A patent/EP1173522A1/en not_active Withdrawn
- 2000-04-08 JP JP2000612379A patent/JP2002542366A/en active Pending
- 2000-04-08 MX MXPA01010432A patent/MXPA01010432A/en unknown
- 2000-04-08 CA CA002370403A patent/CA2370403A1/en not_active Abandoned
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0679697A2 (en) * | 1994-04-25 | 1995-11-02 | Hoechst Aktiengesellschaft | Black mixtures of reactive azo dyes and their use for dyeing fibrous material containing hydroxy and/or carbonamide groups |
EP0731145A2 (en) * | 1995-03-08 | 1996-09-11 | Hoechst Aktiengesellschaft | Black dyestuff mixtures of fibre reactive azo dyestuffs and their utilization for dyeing of hydroxy- and/or carbonamide group containing fibre material |
EP0735112A2 (en) * | 1995-03-30 | 1996-10-02 | Hoechst Aktiengesellschaft | Mixtures of reactive azo dyes and their use for dyeing fibrous material containing hydroxy and/or carbonamide groups |
EP0827987A2 (en) * | 1996-09-05 | 1998-03-11 | DyStar Textilfarben GmbH & Co. Deutschland KG | Mixtures of azo reactive dyes and their use for dyeing fiber material containing hydroxy or carbonamide groups |
EP0974622A1 (en) * | 1998-07-21 | 2000-01-26 | DyStar Textilfarben GmbH & Co. Deutschland KG | Mixture of water soluble reactive azo dyes, process to manufacture it and its use |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002241637A (en) * | 2001-02-20 | 2002-08-28 | Sumitomo Chem Co Ltd | Reactive dye mixture and application of the same to fiber material |
JP4639490B2 (en) * | 2001-02-20 | 2011-02-23 | 住友化学株式会社 | Reactive dye mixtures and their application to textile materials |
EP1437388A1 (en) * | 2003-01-08 | 2004-07-14 | Fuji Photo Film Co., Ltd. | Coloring composition and inkjet recording method |
US7250079B2 (en) | 2003-01-08 | 2007-07-31 | Fujifilm Corporation | Coloring composition and inkjet recording method |
WO2005040285A1 (en) * | 2003-10-20 | 2005-05-06 | Ciba Specialty Chemicals Holding Inc. | Mixtures of reactive dyes and their use |
Also Published As
Publication number | Publication date |
---|---|
MXPA01010432A (en) | 2002-03-27 |
CN1344294A (en) | 2002-04-10 |
BR0009692A (en) | 2002-01-08 |
TR200102952T2 (en) | 2002-04-22 |
EP1173522A1 (en) | 2002-01-23 |
KR20020033090A (en) | 2002-05-04 |
CA2370403A1 (en) | 2000-10-26 |
JP2002542366A (en) | 2002-12-10 |
AU4294600A (en) | 2000-11-02 |
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 (en) | Fiber-reactive black dye mixtures | |
US6165231A (en) | Dye mixture, process for it's preparation and use thereof | |
EP1035173B1 (en) | Black dye mixtures of fiber-reactive azo dyes and use thereof for dyeing hydroxy-and/or carboxamido-containing fiber material | |
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 (en) | Blue dyeing mixture of fiber-reactive dye and method for using it to dye fibrous material containing hydroxyl and/or carboxyamide groups | |
EP0974621B1 (en) | Navy-blue dye mixtures of fiber reactive azo dyes | |
EP1155089B1 (en) | Deep black dye mixtures of fiber-reactive azo dyes and a process for dyeing hydroxy and/or carboxamido containing fibers | |
US5931974A (en) | Deep black dye mixtures of fiber-reactive azo dyes and use thereof for dyeing hydroxy- and/or carboxamido-containing fiber material | |
EP1213329B1 (en) | Black dye mixtures of fiber-reactive azo dyes, methods for their preparation and use thereof for dyeing hydroxy-and/or carboxamido-containing fiber material | |
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 (en) | Dye mixtures of fiber-reactive azo dyes and use thereof for dyeing material containing hydroxy and/or carboxamido groups | |
EP0982374B1 (en) | Black dye mixtures of fiber-reactive azo dyes and use thereof for dyeing hydroxy-and/or carboxamido-containing fiber material | |
EP1305369A2 (en) | Gelbe reaktive monoazofarbstoffe, verfahren zu ihrer herstellung und ihre verwendung | |
EP1090962B1 (en) | Dye mixtures of fiber-reactive azo dyes and use thereof for dyeing material containing hydroxy- and/or carboxamido groups | |
WO2000063298A1 (en) | Deep navy dye mixtures of fiber-reactive azo dyes and a method for their preparation and a process for dyeing hydroxy and/or carboxamido containing fibers | |
EP1046678B1 (en) | Dye mixtures of fiber-reactive azo dyes and use thereof for dyeing material containing hydroxy-and/or carboxamido groups | |
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 (en) | Black dye mixtures of fiber-reactive azo dyes, methods for their preparation and use thereof for dyeing hydroxy- and/or carboxamido-containing fiber material | |
MXPA99008964A (en) | Mixtures of water soluble reactive azo dyes, process to manufacture them and their use |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 00805263.8 Country of ref document: CN |
|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AL AM AT AU AZ BA BB BG BR BY CA CH CN CR CU CZ DE DK DM EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT UA UG US UZ VN YU ZA ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): GH GM KE LS MW SD SL SZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG |
|
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2000922621 Country of ref document: EP |
|
REG | Reference to national code |
Ref country code: DE Ref legal event code: 8642 |
|
ENP | Entry into the national phase |
Ref document number: 2370403 Country of ref document: CA Ref document number: 2370403 Country of ref document: CA Kind code of ref document: A Ref document number: 2000 612379 Country of ref document: JP Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: PA/a/2001/010432 Country of ref document: MX Ref document number: 1020017012980 Country of ref document: KR Ref document number: 2001/02952 Country of ref document: TR |
|
WWP | Wipo information: published in national office |
Ref document number: 2000922621 Country of ref document: EP |
|
WWP | Wipo information: published in national office |
Ref document number: 1020017012980 Country of ref document: KR |
|
WWW | Wipo information: withdrawn in national office |
Ref document number: 2000922621 Country of ref document: EP |
|
WWW | Wipo information: withdrawn in national office |
Ref document number: 1020017012980 Country of ref document: KR |