WO2011020789A1 - Disperse dye mixtures, their preparation and use - Google Patents

Disperse dye mixtures, their preparation and use Download PDF

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Publication number
WO2011020789A1
WO2011020789A1 PCT/EP2010/061821 EP2010061821W WO2011020789A1 WO 2011020789 A1 WO2011020789 A1 WO 2011020789A1 EP 2010061821 W EP2010061821 W EP 2010061821W WO 2011020789 A1 WO2011020789 A1 WO 2011020789A1
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WIPO (PCT)
Prior art keywords
hydrogen
alkoxy
dye
alkyl
methyl
Prior art date
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Ceased
Application number
PCT/EP2010/061821
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French (fr)
Inventor
Adrian Murgatroyd
Clemens Grund
Timo Liebig
Stefan Neubauer
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 Colours Distribution GmbH
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Dystar Colours Deutschland GmbH
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
Priority to ES10742000T priority Critical patent/ES2428269T3/en
Priority to CA2771450A priority patent/CA2771450C/en
Priority to KR1020127003856A priority patent/KR101718566B1/en
Priority to MX2011013214A priority patent/MX2011013214A/en
Priority to CN201080035365.8A priority patent/CN102471996B/en
Priority to EP10742000.2A priority patent/EP2467531B1/en
Application filed by Dystar Colours Deutschland GmbH filed Critical Dystar Colours Deutschland GmbH
Priority to JP2012525148A priority patent/JP5791603B2/en
Priority to BR112012003715A priority patent/BR112012003715B1/en
Publication of WO2011020789A1 publication Critical patent/WO2011020789A1/en
Anticipated expiration legal-status Critical
Priority to US13/622,741 priority patent/US9023117B2/en
Ceased legal-status Critical Current

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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
    • 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
    • C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/0082—Digital printing on bodies of particular shapes
    • 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
    • C09B56/00—Azo dyes containing other chromophoric systems
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/34—Hot-melt inks
    • 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
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/30—Ink jet printing

Definitions

  • Disperse dye mixtures their preparation and use
  • the present invention relates to disperse dyes for dyeing hydrophobic textile materials.
  • WO2008/049758 A2 discloses disperse azo dyes in which a 2-oxoalkyl ester is linked to the chromophore.
  • the present invention provides dye mixtures containing at least one dye of formula (I)
  • T 1 is hydrogen, halogen, trifluoromethyl, cyano, -SCN, -SO 2 CH 3 or nitro;
  • T 2 is hydrogen or halogen
  • R 1 is hydrogen, (C r C 6 )-alkyl, (Ci-C 4 )-alkoxy, halogen, -NHCHO,
  • R 2 is hydrogen or halogen
  • R 3 is hydrogen, (C r C 6 )-alkyl, cyano-, (C r C 4 )-alkoxy-, phenoxy- or phenyl- substituted (C r C 6 )-alkyl, (C 3 -C 4 )-alkenyl or substituted (C 3 -C 4 )-alkenyl;
  • R 4 is hydrogen or methyl
  • R 5 is methyl or ethyl
  • R 6 is hydrogen or methyl
  • R 7 is hydrogen or methyl
  • n 0, 1 , 2 or 3;
  • R 8 and R 9 are each independently hydrogen, (Ci-C 4 )-alkoxy, (C 2 -C 4 )-alkenyloxy or -O(CH 2 ) q R 22 ;
  • q is an integer from 1 to 6;
  • R 22 is 2-tetrahydropyranyl, 2-tetrahydrofuranyl, -OR 23 or -COR 24 ;
  • R 23 is hydrogen, (Ci-C 4 )-alkyl, (C 2 -C 4 )-alkenyl, substituted or unsubstituted phenyl,
  • R 24 is (Ci-C 4 )-alkoxy, (C 2 -C 4 )-alkenyloxy, substituted or unsubstituted phenyloxy, phenyl-(C r C 2 )-alkoxy, phenoxy-(C r C 4 )-alkoxy, (C 2 -C 4 )-alkenyloxy-(C r C 4 )- alkoxy or (CrC ⁇ -alkoxy-CCrC ⁇ -alkoxy.
  • (Ci-C 6 )-alkyl groups may be straight chain or branched and are for example methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, tert- butyl, n-pentyl or n-hexyl.
  • alkoxy groups which are methoxy or ethoxy for example.
  • (C 3 -C 4 )-Alkenyl groups are more particularly allyl
  • (C 2 -C 4 )- alkenyl groups are more particularly vinyl or allyl.
  • Substituents for (C 3 -C 4 )-alkenyl are for example halogen and phenyl.
  • Aryl is more particularly phenyl or naphthyl.
  • Substituents for phenyl or phenoxy are for example halogen, methyl, ethyl, hydroxyethyl, methoxy, ethoxy, hydroxyl and cyano.
  • -NHS ⁇ 2aryl is more particularly phenylsulfonylamino.
  • Halogen is preferably chlorine or bromine.
  • Preferred dye mixtures according to the present invention contain at least one dye of formula (I) where
  • T 1 is hydrogen, chlorine, bromine, trifluoromethyl, cyano or nitro;
  • T 2 is hydrogen or chlorine
  • R 1 is hydrogen, chlorine, methyl, acetylamino, propionylamino, benzoylamino; methylsulfonylamino, ethylsulfonylamino or phenylsulfonylamino;
  • R 2 is hydrogen or chlorine
  • R 3 is hydrogen, methyl, ethyl, propyl, butyl, benzyl, phenylethyl, phenoxyethyl, methoxyethyl, cyanoethyl or allyl;
  • R 4 , R 6 and R 7 are each hydrogen
  • R 5 is methyl
  • n O or i .
  • Particularly preferred dye mixtures according to the present invention contain at least one dye of formula (I) where
  • T 1 is hydrogen, chlorine, bromine, trifluoromethyl, cyano or nitro;
  • T 2 is hydrogen or chlorine
  • R 1 is hydrogen, methyl or acetylamino
  • R 2 is hydrogen or chlorine
  • R 3 is hydrogen, methyl, ethyl, n-butyl, benzyl, phenylethyl, phenoxyethyl,
  • R 4 , R 6 and R 7 are each hydrogen
  • R 5 is methyl
  • n 0.
  • Very particularly preferred dye mixtures according to the present invention contain at least one dye of formula (Ia)
  • T 1 , T 2 and R 1 to R 3 are each as defined in the table which follows:
  • dye mixtures according to the present invention contain at least one dye of formula (II) where
  • R 8 and R 9 are each independently hydrogen, (C r C 4 )-alkoxy or -O(CH 2 ) q R 22 where q is an integer from 1 to 3;
  • R 22 is 2-tetrahydropyranyl, 2-tetrahydrofuranyl, -OR 23 or -COR 24 ;
  • R 23 is hydrogen or (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl
  • R 24 is (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkoxy.
  • Further particularly preferred dye mixtures according to the present invention contain at least one dye of formula (II) where
  • R 8 is hydrogen, (C r C 4 )-alkoxy or -O(CH 2 ) q R 22 , where
  • q is an integer from 1 to 3;
  • R 22 is 2-tetrahydropyranyl, 2-tetrahydrofuranyl, -OR 23 or -COR 24 ; where R 23 is hydrogen or (Ci-C 4 )-alkoxy-(Ci-C 4 )-alkyl; and
  • R 24 is (Ci-C 4 )-alkoxy-(Ci-C 4 )-alkoxy
  • R 9 is hydrogen, (C r C 4 )-alkoxy or -O(CH 2 ) q R 22 , where
  • q is an integer from 1 to 3;
  • R 22 is -COR 24 and
  • R 24 is (CrC 4 )-alkoxy-(CrC 4 )-alkoxy.
  • dye mixtures according to the present invention contain at least one dye of formula (II) where R 8 and R 9 are each as defined in the table which follows and * represents the bond to the phenyl radical:
  • Very particularly preferred dye mixtures according to the present invention contain the dyes of formulae la-11 , la-23, la-24 and/or la-25 together with the dyes of formulae 11-1 , II-2, II-3, II-8 and/or 11-1.
  • the dye mixtures according to the present invention contain the dyes of formulae (I) and (II) more particularly in amounts each from 1% to 99% by weight, more preferably in amounts of in each case 20% to 80% by weight.
  • Very particularly preferred dye mixtures according to the present invention contain dyes of formula (I) in amounts from 30% to 45% by weight and dyes of formula (II) in amounts from 55% to 70% by weight.
  • Suitable mixing ratios for dye of formula (l):dye of formula (II) are 90:10, 80:20, 75:25, 70:30, 60:40, 55:45, 50:50, 45:55, 40:60, 30:70, 25:75, 20:80 and 10:90.
  • the dye mixtures according to the present invention are obtainable by mechanically mixing the dyes of formulae (I) and (II). The amounts are more particularly chosen so as to produce mixtures having the desired compositions.
  • the dyes of formula (I) are known and are described for example in
  • the dyes of formula (II) are known and described for example in EP 0 033 583 A1 and EP 0 397 170 A1.
  • the dye mixtures according to the present invention are very useful for dyeing and printing hydrophobic materials in that the dyeings and prints obtained are notable for level shades and high service fastnesses. Deserving of particular mention are good wash and contact fastnesses and also excellent color buildup properties, especially on polyester and polyester-elastane materials.
  • the present invention thus also provides for the use of the dye mixtures of the present invention for dyeing and printing hydrophobic materials, i.e., processes for dyeing or printing such materials in a conventional manner wherein a dye mixture according to the present invention is used as a colorant.
  • the hydrophobic materials mentioned can be of synthetic or semisynthetic origin. Examples include secondary cellulose acetate, cellulose triacetate, polyamides, polylactides and more particularly high molecular weight polyesters. Materials composed of high molecular weight polyester are more particularly those based on polyethylene terephthalates or polytrimethylene terephthalates. Blend fabrics and blend fibers such as for example polyester-cotton or polyester-elastane are also possible.
  • the hydrophobic synthetic materials can be present in the form of self- supporting film/sheeting or fabric- or thread-shaped bodies and may for example have been processed into yarns or woven or knitted textile fabrics. Preference is given to fibrous textile materials, which may also be present in the form of microfibers for example.
  • the dyeing in accordance with the use provided by the present invention can be effected in a conventional manner, preferably from an aqueous dispersion, if appropriate in the presence of carriers, at between 80 to about 110 0 C by the exhaust process or in a dyeing autoclave at 110 to 140 0 C by the HT process, and also by the so-called thermofix process, in which the fabric is padded with the dyeing liquor and subsequently fixed/set at about 180 to 230 0 C.
  • Printing of the materials mentioned can be carried out in a manner known per se by incorporating the dye mixtures of the present invention in a print paste and treating the fabric printed therewith at temperatures between 180 to 230 0 C with HT steam, high-pressure steam or dry heat, if appropriate in the presence of a carrier, to fix the dye.
  • the dye mixtures of the present invention shall be in a very fine state of subdivision when they are used in dyeing liquors, padded liquors or print pastes.
  • the dyes are converted into the fine state of subdivision in a conventional manner by slurrying them together with dispersants in a liquid medium, preferably water, and subjecting the mixture to the action of shearing forces to mechanically comminute the originally present dye particles to such an extent that an optimal specific surface area is achieved and sedimentation of the dye is minimized. This is accomplished in suitable mills, such as ball or sand mills.
  • the particle size of the dyes is generally between 0.5 and 5 ⁇ m, and preferably equal to about 1 ⁇ m.
  • the dispersants used in the milling operation can be nonionic or anionic.
  • Nonionic dispersants are for example reaction products of alkylene oxides, for example ethylene oxide or propylene oxide, with alkylatable compounds, for example fatty alcohols, fatty amines, fatty acids, phenols, alkylphenols and carboxamides.
  • Anionic dispersants are for example lignosulfonates, alkyl- or alkylarylsulfonates or alkylaryl polyglycol ether sulfates.
  • the dye preparations thus obtained shall be pourable for most applications.
  • the dye and dispersant content is limited in these cases.
  • the dispersions are adjusted to a dye content of up to 50 percent by weight and a dispersant content of up to about 25 percent by weight.
  • dye contents are in most cases not below 15 percent by weight.
  • the dispersions may also contain still further auxiliaries, for example those which act as an oxidizing agent, for example sodium m-nitrobenzenesulfonate, or fungicidal agents, for example sodium o-phenylphenoxide and sodium pentachlorophenoxide, and particularly so-called "acid donors", examples being butyrolactone,
  • monochloroacetamide sodium chloroacetate, sodium dichloroacetate, the sodium salt of 3-chloropropionic acid
  • monosulfate esters such as lauryl sulfate for example
  • sulfuric esters of ethoxylated and propoxylated alcohols for example butylglycol sulfate.
  • the dye dispersions thus obtained are very advantageous for making up dyeing liquors and print pastes.
  • powder formulations contain the dye, dispersants and other auxiliaries, for example wetting, oxidizing, preserving and dustproofing agents and the abovementioned "acid donors”.
  • a preferred method of making pulverulent dye preparations consists in stripping the above-described liquid dye dispersions of their liquid, for example by vacuum drying, freeze drying, by drying on drum dryers, but preferably by spray drying.
  • the dyeing liquors are made by diluting the requisite amounts of the above-described dye formulations with the dyeing medium, preferably water, such that a liquor ratio of
  • 5:1 to 50:1 is obtained for dyeing.
  • further dyeing auxiliaries such as dispersing, wetting and fixing auxiliaries, to the liquors.
  • Organic and inorganic acids such as acetic acid, succinic acid, boric acid or phosphoric acid are added to set a pH in the range from 4 to 5, preferably 4.5. It is advantageous to buffer the pH setting and to add a sufficient amount of a buffering system.
  • the acetic acid/sodium acetate system is an example of an advantageous buffering system.
  • the present invention also provides inks for digital textile printing by the ink jet process, said inks containing a dye mixture according to the present invention.
  • the inks of the present invention are preferably aqueous and contain dye mixtures of the present invention in amounts ranging for example from 0.1 % to 50% by weight, preferably in amounts ranging from 1% to 30% by weight and more preferably in amounts ranging from 1 % to 15% by weight based on the total weight of the ink. They further contain more particularly from 0.1% to 20% by weight of a dispersant. Suitable dispersants are known to a person skilled in the art, are commercially available and include for example sulfonated or sulfomethylated lignins,
  • condensation products of aromatic sulfonic acids and formaldehyde condensation products of optionally substituted phenol and formaldehyde, polyacrylates and corresponding copolymers, modified polyurethanes and reaction products of alkylene oxides with alkylatable compounds, for example fatty alcohols, fatty amines, fatty acids, carboxamides and optionally substituted phenols.
  • the inks according to the present invention may further contain the customary additives, for example viscosity moderators to set viscosities in the range from 1.5 to 40.0 mPas in the temperature range from 20 to 50 0 C.
  • Preferred inks have a viscosity in the range from 1.5 to 20 mPas and particularly preferred inks have a viscosity in the range from 1.5 to 15 mPas.
  • Suitable viscosity moderators are rheological additives, for example polyvinyl caprolactam, polyvinylpyrrolidone and also their copolymers, polyetherpolyol, associative thickeners, polyurea, sodium alginates, modified galactomannans, polyetherurea, polyurethane and nonionic cellulose ethers.
  • the inks according to the present invention may contain surface-active substances to set surface tensions in the range from 20 to 65 mN/m, which are adapted as appropriate depending on the process used (thermal or piezo technology).
  • Suitable surface-active substances are for example surfactants of any kind, preferably nonionic surfactants, butyldiglycol and 1 ,2-hexanediol.
  • the inks may further contain customary additions, for example substances to inhibit fungal and bacterial growth in amounts from 0.01 % to 1 % by weight based on the total weight of the ink.
  • the inks according to the present invention are obtainable in a conventional manner by mixing the components in water.
  • Example 1
  • the mixture is ground as a 40% aqueous suspension with 100 parts of a high temperature stable dispersant until the particle size (diameter) has reached the size magnitude of 0.1 - 5 micrometers.
  • This dispersion is standardized to a solid product containing 25% of the dye mixture and 70% dispersant, by adding 99.7 parts of a "cutting agent" and by drying in a spray dryer either in powder form,
  • Polyester microfiber requires proportionally more of the mixture to achieve a comparable depth of shade to conventional polyester.
  • Example 1 is repeated in similar fashion to obtain the dye mixtures of examples 2 to 20 according to the invention and use them for dyeing polyester.
  • the table which follows indicates the fraction of the respective dye in % by weight based on the total dye content.
  • a textile fabric consisting of polyester is pad-mangled with the liquor consisting of
  • the textile thus pretreated is printed with an aqueous ink prepared in accordance with the procedure described above and containing

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Coloring (AREA)

Abstract

The present invention provides dye mixtures containing at least one dye of formula (I) and at least one dye of formula (II) where T1,T2, R1 to R9 and n are each as defined in claim 1, processes for their preparation and their use.

Description

DyStar Colours Deutschland GmbH
Disperse dye mixtures, their preparation and use The present invention relates to disperse dyes for dyeing hydrophobic textile materials.
Mixtures of benzodifuranone and disperse azo dyes are already known and are described for example in EP 0 305 886 A2, EP 0 640 667 A1 and
WO2008/074719 A1.
In addition, WO2008/049758 A2 discloses disperse azo dyes in which a 2-oxoalkyl ester is linked to the chromophore.
It has now been found that the hereinbelow defined mixtures of benzodifuranone and disperse azo dyes are distinctly improved over the individual dyes in respect of the buildup of the dyeings on polyester and polyester-elastane materials.
The present invention provides dye mixtures containing at least one dye of formula (I)
Figure imgf000003_0001
and at least one dye of formula (II)
Figure imgf000003_0002
where
T1 is hydrogen, halogen, trifluoromethyl, cyano, -SCN, -SO2CH3 or nitro;
T2 is hydrogen or halogen;
R1 is hydrogen, (CrC6)-alkyl, (Ci-C4)-alkoxy, halogen, -NHCHO,
-NHCO(Ci-C6)-alkyl, -NHCOaryl, -NHSO2(Ci-C6)-alkyl or -NHSO2aryl;
R2 is hydrogen or halogen;
R3 is hydrogen, (CrC6)-alkyl, cyano-, (CrC4)-alkoxy-, phenoxy- or phenyl- substituted (CrC6)-alkyl, (C3-C4)-alkenyl or substituted (C3-C4)-alkenyl;
R4 is hydrogen or methyl;
R5 is methyl or ethyl;
R6 is hydrogen or methyl;
R7 is hydrogen or methyl;
n is 0, 1 , 2 or 3;
R8 and R9 are each independently hydrogen, (Ci-C4)-alkoxy, (C2-C4)-alkenyloxy or -O(CH2)qR22; and
q is an integer from 1 to 6; and
R22 is 2-tetrahydropyranyl, 2-tetrahydrofuranyl, -OR23 or -COR24; where
R23 is hydrogen, (Ci-C4)-alkyl, (C2-C4)-alkenyl, substituted or unsubstituted phenyl,
(CrC4)-alkoxy-(CrC4)-alkyl, phenoxy-(CrC4)-alkyl, carbonyl-(CrC4)-alkyl, carbonyl-(C2-C4)-alkenyl, carbonylphenyl, carbonyl-(CrC4)-alkoxy-(C2-C4)- alkyl or carbonylphenoxy-(C2-C4)-alkyl; and
R24 is (Ci-C4)-alkoxy, (C2-C4)-alkenyloxy, substituted or unsubstituted phenyloxy, phenyl-(CrC2)-alkoxy, phenoxy-(CrC4)-alkoxy, (C2-C4)-alkenyloxy-(CrC4)- alkoxy or (CrC^-alkoxy-CCrC^-alkoxy.
In the context of the present invention, (Ci-C6)-alkyl groups may be straight chain or branched and are for example methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, tert- butyl, n-pentyl or n-hexyl. A similar logic holds for alkoxy groups, which are methoxy or ethoxy for example. (C3-C4)-Alkenyl groups are more particularly allyl, (C2-C4)- alkenyl groups are more particularly vinyl or allyl.
Substituents for (C3-C4)-alkenyl are for example halogen and phenyl.
Aryl is more particularly phenyl or naphthyl. Substituents for phenyl or phenoxy are for example halogen, methyl, ethyl, hydroxyethyl, methoxy, ethoxy, hydroxyl and cyano. -NHSθ2aryl is more particularly phenylsulfonylamino. Halogen is preferably chlorine or bromine.
Preferred dye mixtures according to the present invention contain at least one dye of formula (I) where
T1 is hydrogen, chlorine, bromine, trifluoromethyl, cyano or nitro;
T2 is hydrogen or chlorine;
R1 is hydrogen, chlorine, methyl, acetylamino, propionylamino, benzoylamino; methylsulfonylamino, ethylsulfonylamino or phenylsulfonylamino;
R2 is hydrogen or chlorine;
R3 is hydrogen, methyl, ethyl, propyl, butyl, benzyl, phenylethyl, phenoxyethyl, methoxyethyl, cyanoethyl or allyl;
R4, R6 and R7 are each hydrogen;
R5 is methyl; and
n is O or i .
Particularly preferred dye mixtures according to the present invention contain at least one dye of formula (I) where
T1 is hydrogen, chlorine, bromine, trifluoromethyl, cyano or nitro;
T2 is hydrogen or chlorine;
R1 is hydrogen, methyl or acetylamino;
R2 is hydrogen or chlorine;
R3 is hydrogen, methyl, ethyl, n-butyl, benzyl, phenylethyl, phenoxyethyl,
cyanoethyl or allyl;
R4, R6 and R7 are each hydrogen;
R5 is methyl; and
n is 0.
Very particularly preferred dye mixtures according to the present invention contain at least one dye of formula (Ia)
Figure imgf000006_0001
where T1, T2 and R1 to R3 are each as defined in the table which follows:
Figure imgf000006_0002
Figure imgf000007_0001
Further preferred dye mixtures according to the present invention contain at least one dye of formula (II) where
R8 and R9 are each independently hydrogen, (CrC4)-alkoxy or -O(CH2)qR22 where q is an integer from 1 to 3; and
R22 is 2-tetrahydropyranyl, 2-tetrahydrofuranyl, -OR23 or -COR24; where
R 23 is hydrogen or (C1-C4)-alkoxy-(C1-C4)-alkyl; and
R 24 is (C1-C4)-alkoxy-(C1-C4)-alkoxy. Further particularly preferred dye mixtures according to the present invention contain at least one dye of formula (II) where
R8 is hydrogen, (CrC4)-alkoxy or -O(CH2)qR22, where
q is an integer from 1 to 3; and
R22 is 2-tetrahydropyranyl, 2-tetrahydrofuranyl, -OR23 or -COR24; where R23 is hydrogen or (Ci-C4)-alkoxy-(Ci-C4)-alkyl; and
R24 is (Ci-C4)-alkoxy-(Ci-C4)-alkoxy;
and
R9 is hydrogen, (CrC4)-alkoxy or -O(CH2)qR22, where
q is an integer from 1 to 3; and
R22 is -COR24 and
R24 is (CrC4)-alkoxy-(CrC4)-alkoxy.
Further very particularly preferred dye mixtures according to the present invention contain at least one dye of formula (II) where R8 and R9 are each as defined in the table which follows and * represents the bond to the phenyl radical:
Figure imgf000008_0001
Figure imgf000009_0001
Very particularly preferred dye mixtures according to the present invention contain the dyes of formulae la-11 , la-23, la-24 and/or la-25 together with the dyes of formulae 11-1 , II-2, II-3, II-8 and/or 11-1.
Dye mixtures according to the present invention which contain the dye of
formula la-24 and the dye of formula II-3 are more particularly preferred.
The dye mixtures according to the present invention contain the dyes of formulae (I) and (II) more particularly in amounts each from 1% to 99% by weight, more preferably in amounts of in each case 20% to 80% by weight. Very particularly preferred dye mixtures according to the present invention contain dyes of formula (I) in amounts from 30% to 45% by weight and dyes of formula (II) in amounts from 55% to 70% by weight.
Suitable mixing ratios for dye of formula (l):dye of formula (II) are 90:10, 80:20, 75:25, 70:30, 60:40, 55:45, 50:50, 45:55, 40:60, 30:70, 25:75, 20:80 and 10:90.
The dye mixtures according to the present invention are obtainable by mechanically mixing the dyes of formulae (I) and (II). The amounts are more particularly chosen so as to produce mixtures having the desired compositions. The dyes of formula (I) are known and are described for example in
WO2008/049758. Similarly, the dyes of formula (II) are known and described for example in EP 0 033 583 A1 and EP 0 397 170 A1. The dye mixtures according to the present invention are very useful for dyeing and printing hydrophobic materials in that the dyeings and prints obtained are notable for level shades and high service fastnesses. Deserving of particular mention are good wash and contact fastnesses and also excellent color buildup properties, especially on polyester and polyester-elastane materials.
The present invention thus also provides for the use of the dye mixtures of the present invention for dyeing and printing hydrophobic materials, i.e., processes for dyeing or printing such materials in a conventional manner wherein a dye mixture according to the present invention is used as a colorant.
The hydrophobic materials mentioned can be of synthetic or semisynthetic origin. Examples include secondary cellulose acetate, cellulose triacetate, polyamides, polylactides and more particularly high molecular weight polyesters. Materials composed of high molecular weight polyester are more particularly those based on polyethylene terephthalates or polytrimethylene terephthalates. Blend fabrics and blend fibers such as for example polyester-cotton or polyester-elastane are also possible. The hydrophobic synthetic materials can be present in the form of self- supporting film/sheeting or fabric- or thread-shaped bodies and may for example have been processed into yarns or woven or knitted textile fabrics. Preference is given to fibrous textile materials, which may also be present in the form of microfibers for example.
The dyeing in accordance with the use provided by the present invention can be effected in a conventional manner, preferably from an aqueous dispersion, if appropriate in the presence of carriers, at between 80 to about 1100C by the exhaust process or in a dyeing autoclave at 110 to 1400C by the HT process, and also by the so-called thermofix process, in which the fabric is padded with the dyeing liquor and subsequently fixed/set at about 180 to 2300C. Printing of the materials mentioned can be carried out in a manner known per se by incorporating the dye mixtures of the present invention in a print paste and treating the fabric printed therewith at temperatures between 180 to 2300C with HT steam, high-pressure steam or dry heat, if appropriate in the presence of a carrier, to fix the dye.
The dye mixtures of the present invention shall be in a very fine state of subdivision when they are used in dyeing liquors, padded liquors or print pastes. The dyes are converted into the fine state of subdivision in a conventional manner by slurrying them together with dispersants in a liquid medium, preferably water, and subjecting the mixture to the action of shearing forces to mechanically comminute the originally present dye particles to such an extent that an optimal specific surface area is achieved and sedimentation of the dye is minimized. This is accomplished in suitable mills, such as ball or sand mills. The particle size of the dyes is generally between 0.5 and 5 μm, and preferably equal to about 1 μm.
The dispersants used in the milling operation can be nonionic or anionic. Nonionic dispersants are for example reaction products of alkylene oxides, for example ethylene oxide or propylene oxide, with alkylatable compounds, for example fatty alcohols, fatty amines, fatty acids, phenols, alkylphenols and carboxamides. Anionic dispersants are for example lignosulfonates, alkyl- or alkylarylsulfonates or alkylaryl polyglycol ether sulfates.
The dye preparations thus obtained shall be pourable for most applications.
Accordingly, the dye and dispersant content is limited in these cases. In general, the dispersions are adjusted to a dye content of up to 50 percent by weight and a dispersant content of up to about 25 percent by weight. For economic reasons, dye contents are in most cases not below 15 percent by weight.
The dispersions may also contain still further auxiliaries, for example those which act as an oxidizing agent, for example sodium m-nitrobenzenesulfonate, or fungicidal agents, for example sodium o-phenylphenoxide and sodium pentachlorophenoxide, and particularly so-called "acid donors", examples being butyrolactone,
monochloroacetamide, sodium chloroacetate, sodium dichloroacetate, the sodium salt of 3-chloropropionic acid, monosulfate esters such as lauryl sulfate for example, and also sulfuric esters of ethoxylated and propoxylated alcohols, for example butylglycol sulfate.
The dye dispersions thus obtained are very advantageous for making up dyeing liquors and print pastes.
There are certain fields of use where powder formulations are preferred. These powders contain the dye, dispersants and other auxiliaries, for example wetting, oxidizing, preserving and dustproofing agents and the abovementioned "acid donors".
A preferred method of making pulverulent dye preparations consists in stripping the above-described liquid dye dispersions of their liquid, for example by vacuum drying, freeze drying, by drying on drum dryers, but preferably by spray drying.
The dyeing liquors are made by diluting the requisite amounts of the above-described dye formulations with the dyeing medium, preferably water, such that a liquor ratio of
5:1 to 50:1 is obtained for dyeing. In addition, it is generally customary to add further dyeing auxiliaries, such as dispersing, wetting and fixing auxiliaries, to the liquors.
Organic and inorganic acids such as acetic acid, succinic acid, boric acid or phosphoric acid are added to set a pH in the range from 4 to 5, preferably 4.5. It is advantageous to buffer the pH setting and to add a sufficient amount of a buffering system. The acetic acid/sodium acetate system is an example of an advantageous buffering system.
To use the dye mixture in textile printing, the requisite amounts of the
abovementioned dye formulations are kneaded in a conventional manner together with thickeners, for example alkali metal alginates or the like, and optionally further additives, for example fixation accelerants, wetting agents and oxidizing agents, to give print pastes. The present invention also provides inks for digital textile printing by the ink jet process, said inks containing a dye mixture according to the present invention.
The inks of the present invention are preferably aqueous and contain dye mixtures of the present invention in amounts ranging for example from 0.1 % to 50% by weight, preferably in amounts ranging from 1% to 30% by weight and more preferably in amounts ranging from 1 % to 15% by weight based on the total weight of the ink. They further contain more particularly from 0.1% to 20% by weight of a dispersant. Suitable dispersants are known to a person skilled in the art, are commercially available and include for example sulfonated or sulfomethylated lignins,
condensation products of aromatic sulfonic acids and formaldehyde, condensation products of optionally substituted phenol and formaldehyde, polyacrylates and corresponding copolymers, modified polyurethanes and reaction products of alkylene oxides with alkylatable compounds, for example fatty alcohols, fatty amines, fatty acids, carboxamides and optionally substituted phenols.
The inks according to the present invention may further contain the customary additives, for example viscosity moderators to set viscosities in the range from 1.5 to 40.0 mPas in the temperature range from 20 to 500C. Preferred inks have a viscosity in the range from 1.5 to 20 mPas and particularly preferred inks have a viscosity in the range from 1.5 to 15 mPas.
Suitable viscosity moderators are rheological additives, for example polyvinyl caprolactam, polyvinylpyrrolidone and also their copolymers, polyetherpolyol, associative thickeners, polyurea, sodium alginates, modified galactomannans, polyetherurea, polyurethane and nonionic cellulose ethers.
By way of further additions, the inks according to the present invention may contain surface-active substances to set surface tensions in the range from 20 to 65 mN/m, which are adapted as appropriate depending on the process used (thermal or piezo technology).
Suitable surface-active substances are for example surfactants of any kind, preferably nonionic surfactants, butyldiglycol and 1 ,2-hexanediol.
The inks may further contain customary additions, for example substances to inhibit fungal and bacterial growth in amounts from 0.01 % to 1 % by weight based on the total weight of the ink.
The inks according to the present invention are obtainable in a conventional manner by mixing the components in water. Example 1
a) 50 parts of the dye (la-24)
Figure imgf000014_0001
are mechanically mixed with 50 parts of the dye (II-3)
Figure imgf000014_0002
Then, the mixture is ground as a 40% aqueous suspension with 100 parts of a high temperature stable dispersant until the particle size (diameter) has reached the size magnitude of 0.1 - 5 micrometers.
This dispersion is standardized to a solid product containing 25% of the dye mixture and 70% dispersant, by adding 99.7 parts of a "cutting agent" and by drying in a spray dryer either in powder form,
b) 2 g of the dye mixture obtained as per a) are dispersed in 100 ml of water at 40 - 500C. A dyebath is prepared from 11.5 ml of this aqueous dispersion, 57.5 ml of deionized water and 1.2 ml of buffering solution (pH 4.5) and entered with a 5 g piece of polyester. The dyebath is heated to 1300C and maintained at 130°C for 45 minutes in a Werner Mathis high temperature dyeing machine. After rinsing with water and reduction clearing, the polyester material has a ruby red hue having excellent wash fastnesses. A particularly interesting property of this mixture is the excellent buildup behavior on polyester and polyester microfiber. Polyester microfiber requires proportionally more of the mixture to achieve a comparable depth of shade to conventional polyester. Example 1 is repeated in similar fashion to obtain the dye mixtures of examples 2 to 20 according to the invention and use them for dyeing polyester. The table which follows indicates the fraction of the respective dye in % by weight based on the total dye content.
Figure imgf000015_0001
Example 21
A textile fabric consisting of polyester is pad-mangled with the liquor consisting of
50 g/l of 8% sodium alginate solution, 100 g/l of an 8-12% carob flour ether solution and 5 g/l of mononsodium phosphate in water and then dried. The wet pickup is 70%.
The textile thus pretreated is printed with an aqueous ink prepared in accordance with the procedure described above and containing
3.5% of the dye of example 1 ,
2.5% of Disperbyk 190 dispersant,
30% of 1 ,5-pentanediol, 5% of diethylene glycol monomethyl ether,
0.01 % of Mergal K9N biocide and
58.99% of water
using a drop-on-demand (piezo) ink jet print head. The print is fully dried. Fixing is effected by means of superheated steam at 175°C for 7 minutes. The print is subsequently subjected to an alkaline reduction clear, rinsed warm and then dried.

Claims

What is claimed is:
1. A dye mixture containing at least one dye of formula (I)
Figure imgf000017_0001
and at least one dye of formula (II)
Figure imgf000017_0002
where
T1 is hydrogen, halogen, trifluoromethyl, cyano, -SCN, -SO2CH3 or nitro;
T2 is hydrogen or halogen;
R1 is hydrogen, (CrC6)-alkyl, (CrOO-alkoxy, halogen, -NHCHO,
-NHCO(Ci-C6)-alkyl, -NHCOaryl, -NHSO2(Ci-C6)-alkyl or -NHSO2aryl; R2 is hydrogen or halogen;
R3 is hydrogen, (CrC6)-alkyl, cyano-, (CrC4)-alkoxy-, phenoxy- or phenyl- substituted (CrC6)-alkyl, (C3-C4)-alkenyl or substituted (C3-C4)-alkenyl; R4 is hydrogen or methyl;
R5 is methyl or ethyl;
R6 is hydrogen or methyl;
R7 is hydrogen or methyl;
n is 0, 1 , 2 or 3;
R8 and R9 are each independently hydrogen, (Ci-C4)-alkoxy, (C2-C4)-alkenyloxy or
-O(CH2)qR22; and
q is an integer from 1 to 6; and
R22 is 2-tetrahydropyranyl, 2-tetrahydrofuranyl, -OR23 or -COR24; where R23 is hydrogen, (Ci-C4)-alkyl, (C2-C4)-alkenyl, substituted or unsubstituted phenyl, (Ci-C4)-alkoxy-(Ci-C4)-alkyl, phenoxy-(Ci-C4)-alkyl, carbonyl-(Ci-C4)-alkyl, carbonyl-(C2-C4)-alkenyl, carbonylphenyl, carbonyl-(CrC4)-alkoxy-(C2-C4)- alkyl or carbonylphenoxy-(C2-C4)-alkyl; and
R24 is (Ci-C4)-alkoxy, (C2-C4)-alkenyloxy, substituted or unsubstituted phenyloxy, phenyl-(Ci-C2)-alkoxy, phenoxy-(Ci-C4)-alkoxy, (C2-C4)-alkenyloxy-(Ci-C4)- alkoxy or (CrC^-alkoxy-CCrC^-alkoxy.
2. The dye mixture as claimed in claim 1 , containing at least one dye of formula (I) where
T1 is hydrogen, chlorine, bromine, trifluoromethyl, cyano or nitro;
T2 is hydrogen or chlorine;
R1 is hydrogen, chlorine, methyl, acetylamino, propionylamino, benzoylamino; methylsulfonylamino, ethylsulfonylamino or phenylsulfonylamino;
R2 is hydrogen or chlorine;
R3 is hydrogen, methyl, ethyl, propyl, butyl, benzyl, phenylethyl, phenoxyethyl, methoxyethyl, cyanoethyl or allyl;
R4, R6 and R7 are each hydrogen;
R5 is methyl; and
n is 0 or 1.
3. The dye mixture as claimed in claim 1 , containing at least one dye of formula (I) where
T1 is hydrogen, chlorine, bromine, trifluoromethyl, cyano or nitro;
T2 is hydrogen or chlorine;
R1 is hydrogen, methyl or acetylamino;
R2 is hydrogen or chlorine;
R3 is hydrogen, methyl, ethyl, n-butyl, benzyl, phenylethyl, phenoxyethyl,
cyanoethyl or allyl;
R4, R6 and R7 are each hydrogen;
R5 is methyl; and
n is 0.
4. The dye mixture as claimed in claim 1 , containing at least one dye of formula (Ia)
Figure imgf000019_0001
where T1, T2 and R1 to R3 are each as defined in the table which follows:
Figure imgf000019_0002
Figure imgf000020_0001
5. The dye mixture as claimed in one or more of claims 1 to 4, containing at least one dye of formula (II) where
R8 and R9 are each independently hydrogen, (Ci-C4)-alkoxy or -O(CH2)qR22 where q is an integer from 1 to 3; and
R22 is 2-tetrahydropyranyl, 2-tetrahydrofuranyl, -OR23 or -COR24; where
R23 is hydrogen or (C1-C4)-alkoxy-(C1-C4)-alkyl; and
R24 is (Ci-C4)-alkoxy-(Ci-C4)-alkoxy.
6. The dye mixture as claimed in one or more of claims 1 to 4, containing at least one dye of formula (II) where
R8 is hydrogen, (CrC4)-alkoxy or -O(CH2)qR22, where
q is an integer from 1 to 3; and
R22 is 2-tetrahydropyranyl, 2-tetrahydrofuranyl, -OR23 or -COR24; where
R23 is hydrogen or (Ci-C4)-alkoxy-(Ci-C4)-alkyl; and
R24 is (C1-C4)-alkoxy-(C1-C4)-alkoxy;
and
R9 is hydrogen, (Ci-C4)-alkoxy or -O(CH2)qR22, where
q is an integer from 1 to 3; and
R22 is -COR24 and
R24 is (Ci-C4)-alkoxy-(Ci-C4)-alkoxy.
7. The dye mixture as claimed in one or more of claims 1 to 4, containing at least one dye of formula (II) where R8 and R9 are each as defined in the table which follows and * represents the bond to the phenyl radical:
Figure imgf000021_0001
Figure imgf000022_0001
8. The dye mixture as claimed in one or more of claims 1 to 7, containing the dyes of formulae la-11 , la-23, la-24 and/or la-25 together with the dyes of formulae 11-1 , II-2, II-3, H-S and/or 11-1.
9. The use of a dye mixture as claimed in one or more of claims 1 to 8 for dyeing and printing hydrophobic materials.
10. An ink for digital textile printing by the ink jet process, containing a dye mixture as claimed in one or more of claims 1 to 8.
PCT/EP2010/061821 2009-08-21 2010-08-13 Disperse dye mixtures, their preparation and use Ceased WO2011020789A1 (en)

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JP2016513140A (en) * 2013-01-14 2016-05-12 ダイスター・カラーズ・ディストリビューション・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング Highly wet fast disperse dye mixture
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CN106883641B (en) * 2016-12-31 2019-03-29 浙江龙盛集团股份有限公司 A kind of dispersed ruby dye composition and dye preparations
ES2814375T3 (en) * 2017-10-02 2021-03-26 Dystar Colours Distrib Gmbh High moisture fast dispersing dye mixtures
KR20190096126A (en) * 2018-02-08 2019-08-19 (주)경인양행 Disperse dyes composites and methods of dyeing fiber using the same
EP3715424A1 (en) * 2019-03-27 2020-09-30 DyStar Colours Distribution GmbH High wet fast disperse dye mixtures of n-[4-(5-thiocyanato-2,4-dinitro-phenylazo)-phenyl]-amine derivatives and n-[4-(4-nitro-phenylazo)-phenyl]-amine derivatives
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