WO2007147773A2 - Mélanges de colorants et leur utilisation pour l'impression de matériaux de fibres - Google Patents

Mélanges de colorants et leur utilisation pour l'impression de matériaux de fibres Download PDF

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Publication number
WO2007147773A2
WO2007147773A2 PCT/EP2007/055911 EP2007055911W WO2007147773A2 WO 2007147773 A2 WO2007147773 A2 WO 2007147773A2 EP 2007055911 W EP2007055911 W EP 2007055911W WO 2007147773 A2 WO2007147773 A2 WO 2007147773A2
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WO
WIPO (PCT)
Prior art keywords
dye
hydrogen
printing
sodium
alkyl
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.)
Ceased
Application number
PCT/EP2007/055911
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German (de)
English (en)
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WO2007147773A3 (fr
Inventor
Markus Dorer
Helmut Niederschuh
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
Priority to EP07765426A priority Critical patent/EP2035508A2/fr
Publication of WO2007147773A2 publication Critical patent/WO2007147773A2/fr
Publication of WO2007147773A3 publication Critical patent/WO2007147773A3/fr
Anticipated expiration legal-status Critical
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
    • C09B67/0046—Mixtures of two or more azo dyes
    • C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
    • C09B67/0052—Mixtures of two or more reactive monoazo 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
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • 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

Definitions

  • the invention is in the technical field of fiber-reactive azo dyes.
  • yellow dye mixtures containing at least one vinylsulfongue reflex ambience and at least one monochlorotriazine dye of certain structure can solve this problem and in particular to remedy the shortcomings of the individual dyes.
  • the present invention thus relates to a dye mixture which comprises at least one dye of the general formula (I)
  • R 1 and R 2 independently of one another represent hydrogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy, sulfo, chlorine or bromine;
  • R 3 , R 4 and R 5 are independently hydrogen, (C 1 -C 4 ) -alkyl, sulfo or chloro;
  • R 6 is sulfo
  • R 7 is (CrC 4) alkyl, amino or (C r C 4) alkyl substituted amino by;
  • R 8 is hydrogen or (C r C 4 ) -alkyl;
  • X 1 and X 2 are independently halogen or amino; Y is vinyl or -CH 2 CH 2 -Z; Z is an alklisch cleavable substituent; M is hydrogen or an alkali metal; and n stands for 0, 1, 2 or 3.
  • (C 1 -C 4 ) -alkyl groups may be straight-chain or branched and are in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl. Preferred are methyl and ethyl. The same applies to (C 1 -C 4 ) -alkoxy groups, with methoxy and ethoxy being preferred.
  • Halogen is in particular fluorine, chlorine and bromine.
  • M standing alkali is especially lithium, sodium and potassium.
  • M is hydrogen or sodium.
  • Alkali-cleavable substituents Z are, for example, halogen atoms, such as chlorine and bromine, ester groups of organic carboxylic and sulfonic acids, such as alkylcarboxylic acids, optionally substituted benzenecarboxylic acids and optionally substituted benzenesulfonic acids, such as the alkanoyloxy groups of 2 to 5 carbon atoms, of which in particular acetyloxy, benzoyloxy, sulfobenzoyloxy , Phenylsulfonyloxy and Toluylsulfonyloxy, further acidic ester groups of inorganic acids, such as phosphoric acid, sulfuric acid and thiosulfuric acid (phosphato, sulfato and thiosulfato), as well dialkylamino groups with alkyl groups of 1 to 4 carbon atoms, such as dimethylamino and diethylamino.
  • the sulfato group Z is preferably vinyl, ⁇ -chloroethyl and particularly preferably ⁇ -sulfatoethyl.
  • the groups "sulfo”, “thiosulfato”, “phosphato”, and “sulfato” include both their acid form and their salt form. Accordingly, sulfo groups correspond to the formula -SO 3 M, thiosulfato of formula -S-SO 3 M, phosphato groups of the formula -OPO 3 M 2 and sulfato groups of the formula -OSO 3 M, where each M is as defined above.
  • the dyes of the general formula (I) may have different fiber-reactive groups -SO 2 -Y.
  • the fiber-reactive groups SO 2 -Y can mean, on the one hand, vinylsulfonyl groups and, on the other hand, groups -CH 2 CH 2 Z, preferably ⁇ -sulfatoethylsulfonyl groups. Containing the dyes of the general formula (I) partially vinylsulfonyl groups, the proportion of each dye with the vinylsulfonyl group is up to about 30 mol%, based on the respective total dye amount of the dye of the general formula (I).
  • R 1 is preferably hydrogen, methyl or methoxy.
  • R 2 and R 3 are preferably hydrogen.
  • R 4 is preferably hydrogen, methyl or methoxy.
  • R 5 is preferably sulfo.
  • R 7 is preferably methyl or amino.
  • R 8 is preferably hydrogen or
  • X 1 is preferably fluorine or chlorine.
  • X 2 is preferably fluorine, chlorine or
  • Amino. n is preferably 2 or 3.
  • Preferred mixtures contain the dye of the general formula (Ia)
  • Y 'for AIIyI or -CH 2 CH 2 OSO 3 M' and M ' are hydrogen, sodium or potassium.
  • the dye mixtures according to the invention contain the dyes of the general formula (I) preferably in an amount of 1 to 99 wt .-%, particularly preferably 10 to 90 wt .-% and most preferably 25 to 75 wt .-%, and the dyes of general formulas (II) preferably in an amount of 1 to 99 wt .-%, particularly preferably 10 to 90 wt .-% and most preferably 25 to 75 wt .-%.
  • the dye mixtures according to the invention can be in the form of solid or liquid (dissolved) commercial forms.
  • they contain, as far as necessary, the usual in water-soluble and especially fiber-reactive dyes electrolyte salts, such as sodium chloride, potassium chloride and sodium sulfate. Furthermore, they may contain the usual in commercial dyes aids, such as buffer substances that can adjust a pH in aqueous solution between 5 and 7, such as sodium acetate, sodium citrate, sodium borate, sodium bicarbonate, sodium dihydrogen phosphate and disodium hydrogen phosphate, also dyeing aids, dedusting and low Quantities of siccatives.
  • dyes aids such as buffer substances that can adjust a pH in aqueous solution between 5 and 7, such as sodium acetate, sodium citrate, sodium borate, sodium bicarbonate, sodium dihydrogen phosphate and disodium hydrogen phosphate, also dyeing aids, dedusting and low Quantities of siccatives.
  • the dye mixtures according to the invention are generally in the form of electrolytic salt-containing powders or granules (hereinafter generally referred to as preparation) with, if appropriate, one or more of the abovementioned auxiliaries.
  • preparation electrolytic salt-containing powders or granules
  • the dye mixture to 20 to 90 wt .-%, based on the preparation, included.
  • the buffer substances are generally present in a total amount of up to 5% by weight, based on the preparation.
  • the total dye content in these aqueous solutions is up to about 50 wt .-%, such as between 5 and 50 wt .-%, wherein the Electrolyte salt content in these aqueous solutions preferably below 10 wt .-%, based on the aqueous solution is.
  • the aqueous solutions (liquid preparations) may contain the mentioned buffer substances usually in an amount of up to 5% by weight, preferably up to 2% by weight.
  • the dye mixtures according to the invention can be prepared in a simple manner by mixing the dyes of the general formulas (I) and (II) in the desired mixing ratio.
  • the dyes can be used in the mixing process both in the form of an aqueous solution, in particular in the form of the resulting in their preparation synthesis solutions, as well as a solid substance, such as in the form of dye powders or granules.
  • the person skilled in the art is familiar with these mixing methods.
  • Dyestuff mixtures according to the invention which comprise dyes of the general formula (I) which have groups of the formula SO 2 -Y in which Y is vinyl can also be prepared from corresponding dye mixtures according to the invention in which Z is ⁇ -chloroethyl, ⁇ -thiosulfatoethyl or ⁇ - Sulfatoethyl can be obtained by the latter groups are converted with the required amount of alkali wholly or partly in vinyl. This transfer takes place in a manner familiar to the person skilled in the art.
  • the dye mixtures according to the invention are isolated from aqueous solution in a manner known per se by salting out, for example with common salt or potassium chloride, or by spray drying or evaporation.
  • the dyes of the general formulas (I) and (II) are known and are described, for example, in DE 1 282 213 (formula (I)) and GB 970475 (formula (M)), and are commercially available.
  • the dye mixtures according to the invention have valuable performance properties and can be used for dyeing and in particular for printing materials containing carbonamide and / or hydroxyl groups. These materials are especially in the form of fibers.
  • the dye mixtures according to the invention for printing wool and silk and in particular of cellulose-containing fiber materials of all kinds. They are preferably also suitable for printing on blended fabrics containing carbonamide and / or hydroxyl group-containing materials. It is also possible to use the dye mixtures according to the invention to print textiles or paper by the inkjet process.
  • the dye mixtures according to the invention provide yellow dyeings or prints with good fastness properties in these applications.
  • the present invention thus also relates to the use of the dye mixtures according to the invention for dyeing or printing
  • fiber materials or fibers is understood to mean, in particular, textile fibers which may be in the form of woven, knitted or spun yarns or in the form of strands or wound bodies.
  • Carbonamide group-containing materials may be of synthetic or natural origin and are present in particular in the form of fibers. Examples are wool and silk.
  • Hydroxy-containing materials are those of natural or synthetic origin such as cellulosic fiber materials or their regenerated products and polyvinyl alcohols.
  • Cellulose fiber materials are preferably cotton, but also other vegetable fibers such as linen, hemp, jute and ramie fibers.
  • Regenerated CeI Iu loose fibers are, for example, rayon and viscose rayon.
  • the dye mixtures according to the invention can be applied and fixed on the abovementioned materials, in particular on the fiber materials mentioned, according to the application techniques known for water-soluble, in particular, those known for fiber-reactive dyes.
  • the case used for printing pastes can except the dye mixtures according to the invention and water contain further additives.
  • Additives are, for example, wetting agents, anti-foaming agents, leveling agents and agents influencing the properties of the textile material, such as softeners and soil-, water- and oil-repellent or water-softening agents.
  • agents which influence the rheology and the running properties, as well as weak oxidizing agents for example anti-reduction agents.
  • printing pastes may also contain natural or synthetic thickeners, such as alginates and cellulose ethers.
  • the amounts of dye can vary within wide limits depending on the desired color depth.
  • the dyes of the general formula (I) are present in amounts of from 0.01 to 15% by weight, in particular in amounts of from 0.1 to 10% by weight, based on the dyestuff or the printing paste.
  • the single phase for example, by printing with a sodium bicarbonate or other acid-binding agent-containing printing paste and subsequent steaming at
  • thermofixing by means of dry heat according to the usual thermofixing hot air is used from 120 to 180 0 C.
  • the acid-binding and the fixing of the dyes on the cellulose fibers causing agents are, for example, water-soluble basic salts of alkali metals and also alkaline earth metals of inorganic or organic acids or compounds which release alkali in the heat.
  • the Alkali metal hydroxides and alkali metal salts of weak to medium inorganic or organic acids to call, of the alkali metal compounds, preferably the sodium and potassium compounds are meant.
  • Such acid-binding agents are, for example, sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, sodium formate, sodium dihydrogen phosphate, disodium hydrogen phosphate, sodium trichloroacetate, water glass or trisodium phosphate.
  • the prints prepared with the dye mixtures according to the invention have a high color strength and a high fiber-dye bond stability in both acidic and alkaline range, furthermore good light fastness and good wet fastness properties, such as washing, water, and perspiration fastness and good ironing fastness and rubbing fastness.
  • the present invention also relates to inks for digital textile printing by the ink-jet process, which are characterized in that they contain a dye mixture according to the invention.
  • the inks according to the invention contain the dye mixture according to the invention, for example in amounts of from 0.1% by weight to 50% by weight, preferably in amounts of from 1% by weight to 30% by weight and more preferably in amounts of 1% by weight. % to 15% by weight based on the total weight of the ink.
  • the inks may also contain mixtures of dye mixtures according to the invention and other dyes which are used in textile printing.
  • a conductivity of 0.5 to 25 mS / m can be set by addition of electrolyte.
  • Suitable electrolytes are, for example: lithium nitrate, potassium nitrate.
  • the inks of the invention can be organic solvents with a
  • Suitable organic solvents are, for example, alcohols, for.
  • alcohols for.
  • B. Polyethylene glycol, polypropylene glycol, Alkylene glycols having 2 to 8 alkylene groups, e.g. For example: monoethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, thioglycol, thiodiglycol, butyl triglycol, hexylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, lower alkyl ethers of polyhydric alcohols, e.g. For example: ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether,
  • Amines such as Example: methylamine, ethylamine, triethylamine, diethylamine, dimethylamine, trimethylamine, dibutylamine, diethanolamine, triethanolamine, N-formylethanolamine, ethylenediamine, urea derivatives such.
  • Amides such as For example: dimethylformamide, dimethylacetamide, acetamide, ketones or ketoalcohols, such as. B.: Acetone, diacetone alcohol, cyclic ethers, such as. B .; Tetrahydrofuran, trimethylolethane, trimethylolpropane, 2-butoxyethanol, benzyl alcohol, 2-butoxyethanol, gamma-butyrolactone, epsilon-caprolactam, furthermore sulfolane, dimethylsulfolane, methylsulfolane, 2,4-dimethylsulfolane,
  • the inks according to the invention may contain the customary additives, such as viscosity moderators to adjust viscosities in the range of 1, 5 to 40.0 mPas in a temperature range of 20 to 50 0 C.
  • Preferred inks have a viscosity of 1.5 to 20 mPas and particularly preferred inks have a viscosity of 1.5 to 15 mPas.
  • Suitable viscosity moderators are theological additives, for example:
  • polyvinylcaprolactam, polyvinylpyrrolidone and their co-polymers polyether polyol, associative thickener, polyurea, polyurethane, sodium alginates, modified galactomannans, polyether urea, polyurethane, nonionic cellulose ethers.
  • the inks of the invention can surface-active substances for the adjustment of surface tensions of 20 to 65 mN / m, which are optionally adjusted depending on the method used (thermal or piezo technology).
  • Suitable surface-active substances are, for example: surfactants of all kinds, preferably nonionic surfactants, butyldiglycol and 1,2-hexanediol.
  • the inks may still contain conventional additives such as fungicidal and bacterial growth inhibiting agents in amounts of from 0.01 to 1% by weight based on the total weight of the ink.
  • the inks of the invention may be prepared in the usual manner by mixing the components in water.
  • the inks of the invention are suitable for use in ink-jet printing processes for printing a wide variety of preprepared cellulose-containing fiber materials of all kinds, as well as silk and wool.
  • the printing inks of the invention are also suitable for printing pretreated hydroxy-containing or amino-containing fibers contained in blend fabrics, z. As mixtures of cotton, silk, wool with polyester fibers or polyamide fibers.
  • the auxiliaries In contrast to conventional textile printing, in which the printing ink already contains all fixing chemicals and thickeners for a reactive dye, in the case of ink-jet printing the auxiliaries must be applied to the textile substrate in a separate pretreatment step.
  • the pretreatment of the textile substrate takes place before printing an aqueous alkaline liquor.
  • Alkali such as sodium carbonate, sodium bicarbonate, sodium acetate, trisodium phosphate, sodium silicate, sodium hydroxide, alkali donors such as sodium chloroacetate, sodium formate, hydrotropes such as urea, reduction inhibitors such as sodium nitrobenzenesulfonates, as well as thickening agents, the flow of the To prevent motifs when applying the ink, these are, for example, sodium alginates, modified polyacrylates or highly etherified galactomannans.
  • suitable applicators such as a 2- or 3-roll pad, with non-contact
  • Spray technologies applied by foam application or with appropriately adapted inkjet technologies in a defined amount evenly on the textile substrate and then dried. After printing, the textile fiber material is dried at 120 to 150 0 C and then fixed.
  • the fixation of the inkjet prints prepared with reactive dyes can be carried out at room temperature, or with saturated steam, with superheated steam, with hot air, with microwaves, with infrared radiation, with laser or electron beams or with other suitable types of energy transfer.
  • this pretreatment can be omitted.
  • alkali is needed, which is applied after the ink-jet printing before the fixing without intermediate drying.
  • Other additives such as urea or thickener can be dispensed with.
  • the prints prepared with the inks of the present invention have high color strength and high fiber-dye bonding stability in both the acidic and alkaline regions, furthermore good fastness to light and good wet fastness properties such as washing, waterfastness and perspiration fastness, as well as good Ironing fastness and rubbing fastness.
  • example 1
  • cellulosic substrates are printed in direct printing by the usual methods, in flat film printing, rotary printing, desktop printing, manual printing after the single phase or two-phase printing.
  • the prints obtained are dried at 100 0 C, fixed and aftertreated in the usual way.
  • Example 2 A textile fabric consisting of mercerized cotton is treated with a
  • An aqueous ink containing 2% of a dye mixture containing 45% by weight of the dye of the formula (Ia) and 55% by weight of the dye of the formula (IIa) is applied to the textile pretreated in this way.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Coloring (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

Mélange de colorants qui contient au moins un colorant de formule générale (I) et au moins un colorant de formule générale (II), les variables étant telles que définies dans la revendication 1. La présente invention concerne également un procédé de préparation dudit mélange et son utilisation.
PCT/EP2007/055911 2006-06-20 2007-06-14 Mélanges de colorants et leur utilisation pour l'impression de matériaux de fibres Ceased WO2007147773A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP07765426A EP2035508A2 (fr) 2006-06-20 2007-06-14 Mélanges de colorants et leur utilisation pour l'impression de matériaux de fibres

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200610028262 DE102006028262A1 (de) 2006-06-20 2006-06-20 Farbstoffmischungen und ihre Verwendung zum Bedrucken von Fasermaterialien
DE102006028262.0 2006-06-20

Publications (2)

Publication Number Publication Date
WO2007147773A2 true WO2007147773A2 (fr) 2007-12-27
WO2007147773A3 WO2007147773A3 (fr) 2008-02-21

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PCT/EP2007/055911 Ceased WO2007147773A2 (fr) 2006-06-20 2007-06-14 Mélanges de colorants et leur utilisation pour l'impression de matériaux de fibres

Country Status (4)

Country Link
EP (1) EP2035508A2 (fr)
DE (1) DE102006028262A1 (fr)
TW (1) TW200817480A (fr)
WO (1) WO2007147773A2 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2743318B1 (fr) * 2011-08-09 2017-11-29 Nippon Kayaku Kabushiki Kaisha Composition d'encre grise pour impression à jet d'encre et procédé pour imprimer des fibres utilisant celle-ci

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0733487B2 (ja) * 1987-12-25 1995-04-12 三菱化学株式会社 水溶性染料混合物
EP0683251B1 (fr) * 1994-05-17 1998-07-08 DyStar Textilfarben GmbH & Co. Deutschland KG Amination de fibres synthétiques cellulosiques
DE19851389A1 (de) * 1998-11-07 2000-05-11 Dystar Textilfarben Gmbh & Co Gelbe Farbstoffmischungen von wasserlöslichen faserreaktiven Azofarbstoffen und ihre Verwendung

Also Published As

Publication number Publication date
EP2035508A2 (fr) 2009-03-18
DE102006028262A1 (de) 2008-01-03
TW200817480A (en) 2008-04-16
WO2007147773A3 (fr) 2008-02-21

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