WO2010094415A1 - Colorants réactifs contenant du fluor - Google Patents

Colorants réactifs contenant du fluor Download PDF

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Publication number
WO2010094415A1
WO2010094415A1 PCT/EP2010/000799 EP2010000799W WO2010094415A1 WO 2010094415 A1 WO2010094415 A1 WO 2010094415A1 EP 2010000799 W EP2010000799 W EP 2010000799W WO 2010094415 A1 WO2010094415 A1 WO 2010094415A1
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Prior art keywords
group
formula
alkyl
alkoxy
substituted
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PCT/EP2010/000799
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English (en)
Inventor
Warren Ebenezer
Stefan Ehrenberg
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Dystar Colours Deutschland Gmbh
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Priority to CN201080007926.3A priority Critical patent/CN102317378B/zh
Publication of WO2010094415A1 publication Critical patent/WO2010094415A1/fr

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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
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
    • C09B62/507—Azo dyes
    • C09B62/513—Disazo or polyazo dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/4401—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system
    • C09B62/4403—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system the heterocyclic system being a triazine ring
    • C09B62/4411—Azo dyes
    • C09B62/4413—Non-metallized monoazo dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
    • C09B62/507—Azo dyes
    • C09B62/51—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
    • C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes

Definitions

  • This invention relates to the technical field of fibre-reactive azo dyes.
  • Dyestuffs and colorants, respectively, containing fluorine atoms in form of a trifluoromethyl group are known and described in literature.
  • GB732121 discloses monozo acid dyestuffs comprising a trifluoromethyl-benzenesulfonic acid.
  • trifluoromethyl groups are within the generic teaching of for example GB 2 259 710 A 1 EP 0 094 020 A1 , EP 0 354 409 A1 , EP 0 385426 A1 , EP 0 433 764 A1 , EP 470 930 A1 , EP 0 603 116 A1 and EP 0 872 523 A2.
  • fibre-reactive dyestuffs containing fluorine atoms as defined below show particularly advantageous fastness profiles when reactively applied to cotton especially in relation to fastness to light, chlorine and perspiration light fastness and additionally exhibit very good levels of build up. Also, the dyestuffs give level shades with good contact fastness after wash off.
  • the present invention provides dyestuffs of the formula (I)
  • R 1 is F or CF 3 ;
  • R 2 is hydrogen, (Ci-C 4 )-alkyl, (C r C 4 )-alkoxy, hydroxy or chlorine;
  • X 1 is an aromatic or heteroaromatic divalent group;
  • RG is a reactive group capable of forming a covalent bond to carboxamido- and/or hydroxyl-containing material under dyeing conditions or a group comprising a reactive group capable of forming a covalent bond to cellulose under dyeing conditions or is hydrogen; a is 0, 1 or 2; b is 1 in case R 1 is CF 3 and is 1 or 2 in case R 1 is F; and
  • M is hydrogen, an alkali metal or an equivalent of an alkaline earth metal.
  • Preferred aromatic or heteroaromatic divalent groups standing for X 1 correspond to one of the formulae (Ilia) to (IHk)
  • Ar is phenylen or phenylen which is substituted by 1 , 2 or 3 substituents selected from the group comprising (Ci-C 4 )-alkyl, (Ci-C 4 )-alkoxy, hydroxy, trifluormethyl, chlorine, fluorine and -SO 3 M;
  • E 1 has one of the meanings of Ar , is naphthyl or naphthyl which is substituted by 1 , 2 or 3 substituents selected from the group comprising (d-C 4 )-alkyl, (C 1 -C 4 J-HIkOXy, - SO 3 M, amino, acetylamino or hydroxy; or is a 5- or 6-membered heterocyclic residue comprising one or two heteroatoms, selected from the group comprising nitrogen, oxygen and sulphur, or is a 5- or 6-membered heterocyclic residue comprising one or two heteroatoms, selected from the group comprising nitrogen, oxygen and sulphur, which is substituted by 1
  • R 7 is (CrC 4 )-alkyl, (CrC 4 )-alkoxy -SO 3 M or hydroxy;
  • R 8 and R 8 ' independently are hydrogen, (C r C 6 )-alkyl, sulfo-(CrC 6 )-alkyl, phenyl or phenyl substituted by (Ci-C 4 )-alkyl, (CrC 4 )-alkoxy, hydroxyl, -SO 3 M 1 halogen,
  • R 8a is hydrogen or acetyl
  • R 5 is (Ci-C 4 )-alkyl or -COOM;
  • R 6 is hydrogen, CN or -CONH 2 ;
  • L is 1 ,2-phenylene, 1 ,3-phenylene or 1 ,4 phenylene, which are unsubstituted or substituted by -SO 3 M 1 -COOM or R 8 , or is (C 2 -C 6 )-alkylene or (Ci-C 4 )-alkylene- phenylene which are unsubstituted or substituted by R 8 ;
  • M is defined as given above; and * is the bond to the group RG.
  • Examples of 5- or 6-membered heterocyclic residues comprising one or two heteroatoms standing for E 1 are pyridones, pyrazolones and diaminopyridines.
  • examples of divalent 5- or 6-membered heterocyclic residues comprising one or two heteroatoms standing for E 2 are divalent pyridone, pyrazolone and diaminopyridine residues.
  • Especially preferred aromatic or heteroaromatic divalent groups standing for X 1 correspond to the formulae (Him) to (NIu)
  • Z 2 is an alkali-eliminatable group; R 8 is defined as given above; A is a group of the formula (Va), (Vb) or (Vc)
  • V is fluorine or chlorine
  • U 1 and U 2 are independently fluorine, chlorine or hydrogen; and Q 1 and Q 2 are independently chlorine, fluorine, cyanamido, hydroxyl, (Ci-C 6 )-alkoxy, phenoxy, sulfophenoxy, mercapto, (Ci-C 6 )-alkylmercapto, pyridino, carboxypyridino, carbamoylpyridino or a group of the formula (Vl) or (VII)
  • R 9 has one of the meanings of R 1 ;
  • R 10 and R 11 independently have one of the meanings of R 1 or combine to form a group of the formula -(CH 2 )j- or of the formula -(CH 2 )2-B 1 -(CH 2 )2-, where j is 4 or 5, B 1 is oxygen, sulfur, sulfonyl or -NR 9 - and R 9 is (d-C 6 )-alkyl;
  • W is phenylene which is unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of (Ci-C 4 )-alkyl, (Ci-C 4 )-alkoxy, carboxyl, sulfo, chlorine and bromine, or is (Ci-C 4 )-alkylenephenylene, (C 2 -C 6 )-alkylene, which may be interrupted by oxygen, sulfur, sulfonyl, amino, carbonyl or carboxamido, or is phenylene CONH phenylene which is unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of (CrC 4 )-alkyl, (Ci-C 4 )-alkoxy, hydroxyl, sulfo, carboxyl, amido, ureido and halogen, or is naphthylene which is unsubstituted or substituted by one or two sulfo groups; and Z 3
  • R 8 and M are defined as given above.
  • alkyl groups may be straight chain or branched and are in particular methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec- butyl and tert-butyl.
  • (Ci-C 6 )-alkyl groups may in addition be n-pentyl or n-hexyl. Methyl and ethyl are preferred.
  • alkoxy groups which accordingly are preferably methoxy and ethoxy and to alkylene groups, which are in particular ethylene, propylene and butylene.
  • Halogen is preferably bromine, chlorine and fluorine.
  • Alkali M is in particular lithium, sodium or potassium; an alkaline earth metal equivalent M is in particular the equivalent of calcium.
  • M is preferably hydrogen or sodium.
  • Alkali-eliminatable groups standing for Z 1 or Z 2 are for example halogen, such as chlorine and bromine; ester groups of organic carboxylic and sulfonic acids, for example alkylcarboxylic acids, substituted or unsubstituted benzenecarboxylic acids and substituted or unsubstituted benzenesulfonic acids, in particular alkanoyloxy of 2 to 5 carbon atoms such as acetyloxy, benzoyloxy, sulfobenzoyloxy, phenylsulfonyloxy and toluylsulfonyloxy; also acidic ester groups of inorganic acids, as of phosphoric acid, sulfuric acid and thiosulfuric acid (phosphato, sulfato and thiosulfato groups) and dialkylamino groups having alkyl groups of 1 to 4 carbon atoms each, such as dimethylamino and diethylamino.
  • Z 1
  • Preferred dyestuffs of the formula (I) correspond to the formulae (Ia) and (Ib)
  • dyestuffs of the formulae (Ia) and (Ib) wherein Z 1 is -CH CH 2 Or -CH 2 CH 2 OSO 3 M 1 , wherein M 1 is hydrogen or sodium.
  • exceptionally preferred dyestuffs of the formula (I) are for example the dyestuffs of the formulae (Ic) to (Ij)
  • a 1 is a group of the formula (Vf), (Vg), (Vh) or (Vi);
  • a 2 is a group of the formula (Vd) or (Ve);
  • R 12 is methyl, methoxy or -SO3M; and Z 1 and M are defined as given above.
  • the dyestuffs of the formula (I) can be prepared by synthesis steps which are known to a skilled person.
  • the compounds of formula (VII) are known and can be prepared by known methods.
  • R 1 is F or CF 3 ;
  • R 2 is hydrogen, (Ci-C 4 )-alkyl, (C 1 -C 4 ⁇ aIkOXy, hydroxy or chlorine; a is 0, 1 or 2; b is 1 in case R 1 is CF 3 and is 1 or 2 in case R 1 is F; and M is hydrogen, an alkali metal or an equivalent of an alkaline earth metal.
  • the present invention's dyes of the formula (I) have useful application properties and can be used for dyeing and printing carboxamido- and/or hydroxyl-containing materials.
  • the materials mentioned can be present for example in the form of sheetlike constructions such as paper and leather, in the form of films, as for example polyamide films, or in the form of a bulk composition, for example composed of polyamide or polyurethane. In particular, however, they are present in the form of fibres of the materials mentioned.
  • the present invention's dyes of the formula (I) are used for dyeing and printing cellulosic fibrous materials of any kind. They are preferably also useful for dyeing or printing polyamide fibres or of blend fabrics of polyamide with cotton or with polyester fibres.
  • the present invention thus also provides for the use of the present invention's dyes of the formula (I) for dyeing or printing carboxamido- and/or hydroxyl-containing materials, or as the case may be for processes for dyeing or printing such materials in a conventional manner wherein one or more dyes of the formula (I) according to the present invention are utilized as a colorant.
  • the as-synthesized solutions of the present invention's dyes of the formula (I), if appropriate after addition of a buffer substance, and if appropriate also after concentrating or diluting, can be directly used for dyeing as a liquid preparation.
  • Fibrous materials or fibres herein refer in particular to textile fibers which can be present as wovens, yarns or in the form of hanks or wound packages.
  • 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.
  • Hydroxyl-containing materials are those of natural or synthetic origin, for example cellulosic fibre materials or their regenerated products and polyvinyl alcohols.
  • Cellulosic fibre materials are preferably cotton, but also other vegetable fibres, such as linen, hemp, jute and ramie fibers.
  • Regenerated fibres of cellulose are for example staple viscose and filament viscose.
  • the present invention's dyes of the formula (I) can be applied to and fixed on the materials mentioned, in particular on the fibrous materials mentioned, by the application techniques known for water-soluble dyes, in particular known for fibre- reactive dyes.
  • Wool which has been given a nonfelting or low-felting finish (cf. for example H. Rath, Lehrbuch der Textilchemie, Springer-Verlag, 3rd edition (1972), pp. 295-299, in particular 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. For instance, 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 dyes of the present invention are preferably subjected to the exhaust 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 optionally weakly alkaline range up to a pH of 8.5 to bring about, especially for very deep shades, the full reactive bond between the dyes of the present invention and the fibre. At the same time, the dye portion not reactively bound is removed.
  • the dyeing liquors and print pastes, as well as the dyes of the formula (I) may contain further additions.
  • Additions are for example wetting agents, antifoam agents, leveling agents and agents which influence the properties of the textile material, such as softeners, additions for a flameproof finish and soil-, water- and oil-rejecting or water-softening agents.
  • Print pastes in particular may also contain natural or synthetic thickeners, such as for example alginates and cellulose ethers.
  • the dye quantities in the dyebaths and print pastes can vary within wide limits according to the desired depth of shade.
  • the dyes of the formula (I) are present in amounts of 0.01 % to 15% by weight and in particular in amounts of 0.1 % to 10% by weight based respectively on the material to be dyed and on the print paste.
  • cellulose fibres they produce by the exhaust method from a long liquor using a wide variety of acid-binding agents and if appropriate neutral salts, such as sodium chloride or sodium sulfate, dyeings having very good color yields.
  • Application of the dye is preferably at a pH of 3 to 7, and in particular at a pH of 4 to 6 for the exhausts method.
  • the liquor ratio can be chosen within a wide range and is for example between 3:1 and 50:1 , preferably between 5:1 and 30:1.
  • Dyeing is preferably carried out in an aqueous bath at temperatures between 40 and 105 0 C, if appropriate at a temperature of up to 13O 0 C under pressure, and if appropriate in the presence of customary dyeing auxiliaries.
  • unfixed dye can be removed in an aftertreatment. This aftertreatment is carried out in particular at a pH of 8 to 9 and temperatures of 75 to 8O 0 C.
  • One possible procedure here is to introduce the material into the warm bath and to gradually heat the bath to the desired temperature and complete the dyeing process at that temperature.
  • the neutral salts which accelerate the exhaustion of the dyes may also if desired only be added to the bath after the actual dyeing temperature has been reached.
  • Padding processes likewise provide excellent color yields and a very good color buildup on cellulose fibres, the dyes being fixable in a conventional manner by batching at room temperature or elevated temperature, for example at up to about 6O 0 C, by steaming or using dry heat.
  • customary printing processes for cellulose fibers which can be carried out in one step, for example by printing with a print paste containing sodium bicarbonate or some other acid-binding agent and by subsequent steaming at 100 to 103 0 C, or in two steps, for example by printing with a neutral or weakly acidic print color and then fixing either by passing the printed material through a hot electrolyte- containing alkaline bath or by overpadding with an alkaline electrolyte-containing padding liquor and subsequent batching or steaming or dry heat treatment of the alkali-overpadded material, produce strong color prints with well-defined contours and a clear white ground. The outcome of the prints is affected by variations in the fixing conditions.
  • thermofix processes When fixing by means of dry heat in accordance with the customary thermofix processes, hot air at 120 to 200 0 C is used. In addition to the customary steam at 101 to 103 0 C, it is also possible to use superheated steam and high-pressure steam at temperatures of up to 16O 0 C.
  • the acid-binding agents which effect the fixation of the dyes on the cellulose fibers are for example water-soluble basic salts of alkali metals and likewise alkaline earth metals of inorganic or organic acids or compounds which liberate alkali in the heat.
  • the alkali metal hydroxides and alkali metal salts of weak to medium inorganic or organic acids are the preferred alkali metal compounds being the sodium and potassium compounds.
  • Such acid-binding agents are for example sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, sodium formate, sodium dihydrogenphosphate, disodium hydrogenphosphate, sodium trichloroacetate, waterglass or trisodium phosphate.
  • the present invention's dyes of the formula (I) are notable for high reactivity, good fixing ability, very good build-up ability and also high light and perspiration light fastness. They can therefore be applied by the exhaust dyeing process at low dyeing temperatures and require only short steam times in the pad-steam process.
  • the degrees of fixation are high and unfixed portions are readily washed off with the difference between the degree of exhaustion and the degree of fixation being remarkably small, i.e., the loss on soaping is very low.
  • They are also particularly useful for printing, particularly on cotton, but also for printing nitrogenous fibers, for example wool or silk or blend fabrics containing wool or silk.
  • the present invention's dyes of the formula (I) are notable for unfixed portions of dye being readily washed off the fibrous material after the dyeing operation without whites included in the washing operation being stained or tainted by the dye which comes off. This results in advantages for the dyeing operation, in which washing cycles and hence costs are saved.
  • the dyeings and prints produced using the present invention's dyes of the formula (I) possess a high color strength and a high fibre-dye bond stability not only in the acidic region but also in the alkaline region, and also good light fastness and very good wet fastness properties, such as wash, water, seawater, cross-dyeing and perspiration fastnesses and also good fastness to pleating, hotpressing and crocking.
  • the present invention also provides inks for digital textile printing by the ink jet process, the inks comprising a present invention's dye of the formula (I).
  • the present invention's inks contain one or more of the present invention's dyes of the formula (I), for example in amounts from 0.1% by weight to 50% by weight, preferably in amounts from 1% by weight to 30% by weight and more preferably in amounts from 1 % by weight to 15% by weight, based on the total weight of the ink.
  • a conductivity of 0.5 to 25 mS/m can be set by adding an electrolyte.
  • Useful electrolytes include for example lithium nitrate and potassium nitrate.
  • the inks of the present invention may include organic solvents at a total level of 1-50% and preferably 5-30% by weight.
  • Suitable organic solvents are for example alcohols, for example methanol, ethanol, 1- propanol, isopropanol, 1-butanol, tert-butanol, pentyl alcohol, polyhydric alcohols for example: 1 ,2-ethanediol, 1 ,2,3-propanetriol, butanediol, 1 ,3-butanediol, 1 ,4- butanediol, 1 ,2-propanediol, 2,3-propanediol, pentanediol, 1 ,4-pentanediol, 1 ,5- pentanediol, hexanediol, D,L-1 ,2-hexanediol, 1 ,6-hexanediol, 1
  • the inks of the invention may further include customary additives, for example viscosity moderators to set viscosities in the range from 1.5 to 40.0 mPas in a temperature range from 20 to 50°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.
  • Useful viscosity moderators include rheological additives, for example polyvinylcaprolactam, polyvinylpyrrolidone and their copolymers polyetherpolyol, associative thickeners, polyurea, polyurethane, sodium alginates, modified galactomannans, polyetherurea, polyurethane and nonionic cellulose ethers.
  • rheological additives for example polyvinylcaprolactam, polyvinylpyrrolidone and their copolymers polyetherpolyol, associative thickeners, polyurea, polyurethane, sodium alginates, modified galactomannans, polyetherurea, polyurethane and nonionic cellulose ethers.
  • the inks of the invention may include surface-active substances to set surface tensions of 20 to 65 mN/m, which are adapted if necessary as a function of the process used (thermal or piezo technology).
  • Useful surface-active substances include for example all surfactants, preferably nonionic surfactants, butyldiglycol and 1 ,2-hexanediol.
  • the inks may further include customary additives, 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.
  • customary additives 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 of the invention may be prepared in a conventional manner by mixing the components in water.
  • the inks of the invention are particularly useful in inkjet printing processes for printing a wide variety of pretreated materials, such as silk, leather, wool, cellulosic fibre materials of any kind, polyurethanes and polyamide fibres.
  • the printing inks of the invention are also suitable for printing pretreated hydroxyl-containing and/or amino- containing fibers present in blends, examples being blends of cotton, silk, wool with polyester fibres or polyamide fibres.
  • auxiliaries In contrast to conventional textile printing, where the printing ink already contains all the fixing chemicals and thickeners for a reactive dye, in inkjet printing the auxiliaries have to be applied to the textile substrate in a separate pretreatment step.
  • the pretreatment of the textile substrate is effected with an aqueous alkaline liquor prior to printing.
  • alkali for example sodium carbonate, sodium bicarbonate, sodium acetate, trisodium phosphate, sodium silicate, sodium hydroxide, alkali donors such as, for example, sodium chloroacetate, sodium formate, hydrotropic substances such as, for example, urea, reduction inhibitors, for example sodium nitrobenzenesulfonates, and also thickeners to prevent flowing of the motives when the printing ink is applied, for example sodium alginates, modified polyacrylates or highly etherified galactomannans.
  • pretreatment reagents are uniformly applied to the textile substrate in a defined amount using suitable applicators, for example using a 2- or 3-roll pad, contactless spraying technologies, by means of foam application or using appropriately adapted inkjet technologies, and subsequently dried.
  • the textile fiber material is dried at 120 to 150 0 C and subsequently fixed.
  • the fixing of the inkjet prints prepared with reactive dyes may be effected 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 energy transfer techniques.
  • the prints produced with the inks of the present invention possess high color strength and a high fiber-dye bond stability not only in the acidic but also in the alkaline region, also good lightfastness and very good wet fastness properties such as fastness to washing, water, seawater, crossdyeing and perspiration, and also good fastness to pleating, hotpressing and crocking.
  • the oil exhibited analytical data consistent with the expected structure.
  • the orange reaction mixture was drowned-out into 2N hydrochloric acid (200ml), initially an oil separated before it solidified to a bright yellow solid.
  • the yellow solid was collected by filtration and pulled dry (26.28g) and was used in the next step without purification.
  • the solid exhibited analytical data consistent with the expected structure.
  • reaction mixture was basified with 10% sodium carbonate (90ml) to pH8.0-8.5 and filtered, solid discarded and the filtrate concentrated in vacuo to dryness. The residue an off-white solid was collected and dried at 4O 0 C and was used in the next stage without purification. The solid exhibited analytical data consistent with the expected structure.
  • a textile fabric consisting of mercerized cotton is padded with a liquor containing
  • the textile thus pretreated is printed with an aqueous ink containing 2% of the dye obtained according to Example 1 , 20% of sulfolane, 0.01% of Mergal K9N and
  • the print is subsequently rinsed warm, subjected to a fastness wash with hot water at 95°C, rinsed warm and then dried to obtain a print having excellent service fastnesses.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Coloring (AREA)

Abstract

La présente invention concerne des colorants de formule (I) dans laquelle X1, RG, R1, R2, Z1, a, b et M sont tels que définis dans la revendication 1, un procédé pour leur préparation et leur utilisation.
PCT/EP2010/000799 2009-02-18 2010-02-10 Colorants réactifs contenant du fluor WO2010094415A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201080007926.3A CN102317378B (zh) 2009-02-18 2010-02-10 含氟活性染料

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EP09153064.2 2009-02-18
EP09153064 2009-02-18

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WO2010094415A1 true WO2010094415A1 (fr) 2010-08-26

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Cited By (2)

* Cited by examiner, † Cited by third party
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KR20150033650A (ko) * 2012-06-15 2015-04-01 훈츠만 어드밴스트 머티리얼스(스위처랜드) 게엠베하 섬유-반응성 염료, 이의 제조 및 이의 용도
CN112679982A (zh) * 2020-12-21 2021-04-20 江苏德美科化工有限公司 一种印花用高固色率高耐氯牢度的多活性基红色染料及其制备方法

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CN110180456B (zh) * 2019-05-16 2021-02-02 万华化学集团股份有限公司 一种多功能表面活性剂及其制备方法、用途

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KR20150033650A (ko) * 2012-06-15 2015-04-01 훈츠만 어드밴스트 머티리얼스(스위처랜드) 게엠베하 섬유-반응성 염료, 이의 제조 및 이의 용도
KR102046778B1 (ko) 2012-06-15 2019-11-20 훈츠만 어드밴스트 머티리얼스(스위처랜드) 게엠베하 섬유-반응성 염료, 이의 제조 및 이의 용도
CN112679982A (zh) * 2020-12-21 2021-04-20 江苏德美科化工有限公司 一种印花用高固色率高耐氯牢度的多活性基红色染料及其制备方法

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