Classifications

• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
  • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
  • D06P1/16—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 dispersed, e.g. acetate, dyestuffs
• • 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
  • D06P1/0004—General aspects of dyeing
  • D06P1/002—Processing by repeated dyeing, e.g. in different baths
• • 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
  • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
  • D06P3/02—Material containing basic nitrogen
  • D06P3/04—Material containing basic nitrogen containing amide groups
  • D06P3/24—Polyamides; Polyurethanes
  • D06P3/26—Polyamides; Polyurethanes using dispersed dyestuffs
• • 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
  • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
  • D06P3/34—Material containing ester groups
  • D06P3/52—Polyesters
  • D06P3/54—Polyesters using dispersed dyestuffs
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
  • Y10S8/904—Mixed anionic and nonionic emulsifiers for dyeing
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
  • Y10S8/906—Mixed cationic and nonionic emulsifiers for dyeing
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
  • Y10S8/907—Nonionic emulsifiers for dyeing
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
  • Y10S8/908—Anionic emulsifiers for dyeing
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
  • Y10S8/92—Synthetic fiber dyeing
  • Y10S8/922—Polyester fiber
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
  • Y10S8/92—Synthetic fiber dyeing
  • Y10S8/924—Polyamide fiber

Definitions

• the present invention relates to a method for dyeing hydrophobic fiber material with unformed disperse dyes, and to the fiber material dyed by the method.
• Hydrophobic fiber material primarily polyester yarns or fabrics or knits made of polyester fibers, are dyed with disperse dyes either under normal pressure, at temperatures up to 100 ° C in the presence of a carrier or in a closed dyeing machine at temperatures from 120 to 150 ° C under pressure.
• disperse dyes are required to carry them out, which are in a finely divided, stable dispersed form. Accordingly, the dyes have to be subjected to lengthy grinding operations after synthesis, for example in agitator ball mills or sand mills, together with suitable dispersants.
• ground-down disperse dye must be transferred to a stable, storable liquid formulation which does not tend to reagglomeration or be subjected to a gentle drying process in order to obtain a dye powder which can be dispersed rapidly in the dye liquor without lump formation.
• hydrophobic fiber material in particular polyester and polyamide fiber material
• the method according to the invention offers considerable advantages.
• unformed dyes i.e. Dyes which are free of dispersants can be dispensed with the dispersants and the complex grinding, thermal stabilization and drying of the dyes.
• the amount of waste water is greatly reduced because the dye baths are used several times. In addition to saving water, this also entails a considerable reduction in energy costs, since the dyed baths that are pulled out do not have to be re-heated from room temperature to the dyeing temperature if they are used again. Only the cooling, which may be necessary without a device for the hot extension of the goods and which occurs during the change of the goods, has to be compensated. Since the undrawn part of the dye is available again for the next dyeing, overall there is less dye and chemical consumption.
• the invention thus relates to a process for dyeing hydrophobic fiber material with unformed disperse dyes from an aqueous liquor, which is characterized in that one or more of these dyes is hydrotroped or stabilized by a surfactant or surfactant mixture on disperse dyes at a temperature of 50 ° to 150 ° C, in particular 70-100 ° C and preferably 90-99 ° C at normal or positive pressure, in water, the dye solution in a dyeing machine with substrate, then the dyeing liquor heated to dyeing temperature and the dyeing (for example HT or carrier) completed at this temperature, and that you then remove the substrate and the extracted dye liquor by adding water, surfactant and dye, the dye being either the same or optionally restores the original composition together with another or only with another and used again for dyeing.
• a surfactant or surfactant mixture on disperse dyes at a temperature of 50 ° to 150 ° C, in particular 70-100 ° C and preferably 90-99 ° C at normal or positive pressure
• the dye liquor is preferably used 5 to 100 times, in particular 5 to 15 times.
• the disperse dyes which can be used according to the invention can belong to a wide variety of dye classes.
• it is azo, anthraquinone, nitro, methine, styryl, azostyryl; Naphthoperinone, quinophthalone, acridone or naphthoquinoneimine dyes that are free from water-solubilizing groups.
• Preferred dispersion dyes are metal-free mono- or disazo dyes, nitro dyes, acridone dyes, anthraquinone dyes or quinophthalone dyes. Dyes which have sufficient water solubility in the presence of hydrotroping or solubilizing surfactants for use in the present process can easily be selected by appropriate preliminary tests.
• the dyes can in principle be used without any aftertreatment, i.e. directly from the synthesis, e.g. in the form of a moist press cake or as an aqueous suspension.
• the disperse dye or dyes are introduced into the dyeing apparatus in the form of a hot aqueous solution or dissolved in the dyeing apparatus before the introduction of the fiber material.
• solution is understood to mean a true monomolecular solution, a colloidal solution and a microdispersion.
• the dye is thus fed to the dye liquor in dissolved, solubilized, hydrotroped or microdispersed form.
• the dye solution can, for example, be fed into the liquor circulating in the dyeing apparatus either by adding all of it, for example in one, connected to the dyeing apparatus Batch container, prepared solution or by metering in portions.
• the latter can be done by appropriate control, for example in relation to the number of pumping cycles, or also as a function of the heating rate, if the dye solution is added to the dye liquor little by little during heating to the dyeing temperature.
• the dye solution has the same temperature as the circulating liquor when it is metered into the dyeing apparatus.
• the method according to the invention can also be carried out using the sluice method or by changing the direction of the fleet.
• a surfactant or surfactant mixture having a hydrotroping or solubilizing effect is used according to the invention.
• they are anionic, nonionic and cationic surfactants.
• amphoteric surfactants can also be used.
• mixtures of a nonionic and an anionic surfactant have proven to be particularly favorable. Mixtures of a nonionic and a cationic surfactant are also suitable.
• the hydrotroping or solubilizing anionic surfactants used are preferably reaction products of ethylene oxide and / or propylene oxide with saturated or unsaturated fatty acids, fatty alcohols, fatty amines, alicyclic alcohols or aliphatic-aromatic hydrocarbons which are terminally esterified by an inorganic oxygen-containing acid or a polybasic carboxylic acid. These are compounds of the formula I.
• R is an aliphatic hydrocarbon radical with 8 to 22 carbon atoms or a cycloaliphatic or aliphatic-aromatic hydrocarbon radical with 10 to 22 carbon atoms
• R 1 is hydrogen or methyl
• a -0 -, - NH- or X the acid residue an inorganic, oxygen-containing acid or the rest of a polybasic carboxylic acid
• m is a number from 1 to 20, in particular 1 to 5.
• the rest RA- is derived, for example, from higher alcohols such as decyl, lauryl, tridecyl, myristyl, cetyl, stearyl, oleyl, arachidyl, hydroabietyl alcohol or behenyl alcohol; also of fatty amines such as stearylamine, palmitylamine or oleylamine; of fatty acids, such as caprylic, capric, lauric, myristic, palmitic, stearic, arachine, behen, coconut fat (C 8 -C 18 ), decene, dodecene, tetradecene, hexadecene, Oleic, linoleic, linolenic, eicotonic, docosonic or clupanodonic acid; of alkylphenols such as butyl, hexyl, n-octyl, n-nonyl, p-tert-
• the acid residue X is usually derived from low molecular weight dicarboxylic acids, such as maleic acid, malonic acid, succinic acid or sulfosuccinic acid, and is connected to the residue RA- (CH 2 CHR i O) - via an ester bridge.
• X is derived from inorganic polybasic acids such as orthophosphoric acid and sulfuric acid.
• the acid residue X is preferably in salt form, ie, for example, as an alkali metal, ammonium or amine salt. Examples of such salts are sodium, potassium, ammonium, trimethylamine, ethanolamine, diethanolamine or triethanolamine salts.
• These compounds are prepared by known methods by adding to the alcohols, fatty amines, acids and alkylphenols mentioned, ethylene oxide and / or propylene oxide and then esterifying the alkoxylates thus obtained and optionally converting the esters into their salts.
• Such surfactants are e.g. known from U.S. Patent 3,211,514.
• the acidic sulfuric acid esters of alkylphenol ethoxylates are in turn preferably used, that is to say those compounds of the formula given in which RA- is an alkylphenol radical, R 1 is hydrogen, m has the meaning given and X represents a sulfuric acid radical.
• the sulfuric acid half-esters of the alkoxylates mentioned are preferably in the form of the ammonium salt. If appropriate, mixtures of the anionic surfactants can also be used.
• Such compounds are known or can be obtained by known processes, for example by reacting a fatty amine or a mixture of fatty amines, such as, for example, coconut fatty amine with ethylene oxide and / or propylene oxide and then quaternizing the alkoxylate thus obtained, e.g. with dimethyl sulfate (see e.g. H. Stache, Tensid-Taschenbuch; Carl Hanser Verlag 1981).
• those cationic surfactants of the formula II have proven particularly useful which, in addition to the higher alkyl radical R 1 as substituents R 2, have a methyl or ethyl radical and in which R 3 is 1 to 4 for an alkyl radical substituted by the phenyl group Carbon atoms; X has the meaning already given. Mixtures of such compounds are also suitable, which are obtained, for example, when starting from fatty amine mixtures, such as coconut fatty amine, for the production of these surfactants.
• N-dodecyl-N N-dimethylamine oxide N-myristyl-N, N-dimethylamine oxide N-dodecyl-N, N-di-2-hydroxyethylamine oxide N-hexadecyl-N, N-di-2-hydroxyethylamine oxide N- Hexadecyl-N, N-dimethylamine oxide N-oleyl-N, N-di-2-hydroxyethylamine oxide N-stearyl-N, N-di-2-hydroxyethylamine oxide N-coconut fatty acid amidopropyl-N, N-dimethylamine oxide N-tallow fatty acid amidopropyl-N, N- dimethylamine oxide.
• Mixtures of the reaction products according to a) to g) can also be used. These mixtures are obtained by mixing individual reaction products or directly by alkoxylating a mixture of the compounds on which the reaction products are based.
• Suitable saturated and / or unsaturated fatty alcohols for b) are dodecanol, hexadecyl alcohol, palmityl alcohol, stearyl alcohol, oleyl alcohol or tallow fatty alcohols, hexanol, 2-ethylhexanol and decanol.
• alkylphenols for c) n-butylphenol, tert-butylphenol, tributylphenol, octylphenol, p-amylphenol, hexalphenol, isooctylphenol, nonylphenol and dodecylphenol are mentioned.
• fatty amine for e come e.g. in addition to stearylamine, palmitylamine and especially oleylamine.
• saturated and / or unsaturated fatty acids are e.g. Palmitic acid, especially stearic acid and oleic acid.
• Reaction products of groups c) and d) have proven to be particularly effective, and especially hydroxybiphenyl ethoxylates, such as reaction products of 6 or 8 moles of ethylene oxide with one mole of o-phenylphenol or C 4 to c 9 alkylphenol ethoxylates, for example Reaction products of 6 to 8 moles of ethylene oxide with one mole of butylphenol.
• ethylene / propylene oxide reaction products are known or can be prepared by processes known per se (see, for example: N. Schönfeldt, interfacially active ethylene oxide adducts;ticianliche Verlagsgesellschaft mbH, Stuttgart; 1976).
• the mixing ratio of nonionic to anionic surfactant is advantageously between 1: 4 and 4: 1. Those surfactant mixtures which contain about twice as much nonionic as anionic surfactant are preferably used.
• a particularly pronounced solubilizing effect has a mixture which contains, as a nonionic component, a reaction product of 1 mol of o-phenylphenol or 1 mol of tert-butylphenol and 6 mol of ethylene oxide and a nonylphenol diglycol ether sulfate as the anionic component; also a mixture of a cationic and a nonionic surfactant, for example a reaction product of 1 mol of o-phenylphenol + 6 mol of ethylene oxide and a product of the formula
• surfactant or surfactant mixture 5 to 100, preferably 10 to 80 and in particular 25 to 45 parts of surfactant or surfactant mixture are used, based on 1 part of disperse dye.
• the amounts in which the disperse dyes are used can vary within wide limits depending on the desired depth of color; in general, amounts of 0.01 to 10 percent by weight of one or more of the stated disperse dyes, based on the material to be dyed, are used.
• the hydrophobic fiber materials that can be dyed by the present process are primarily those made from linear, high molecular weight esters of aromatic polycarboxylic acids with polyfunctional alcohols, for example from terephthalic acid and ethylene glycol or dimethylolcyclohexane and mixed polymers from terephthalic acid and isophthalic acid and ethylene glycol.
• these materials can be used at any stage of processing, e.g. in the form of flakes, sliver, yarn, textured threads, woven or knitted fabrics, as well as a mixed fabric among themselves or with other fibers, for example as a mixed fabric made of polyester / polyamide or polyester / cotton.
• the dyeing temperature for these materials is preferably 120 to 150 ° C for the HT process and up to 100 ° C for the carrier process.
• polyamide material can be dyed by the process according to the invention, e.g. Polyamide-6, polyamide-6,6 or also polyamide 12.
• the dyeing temperature for these materials is preferably 98 to 100 ° C.
• the aqueous liquor can contain customary coloring auxiliaries, advantageously in small amounts, such as acids, in particular an organic lower monocarboxylic acid, e.g. Formic acid or acetic acid, buffer salts such as ammonium sulfate or sodium acetate, wetting agents, emulsifiers or anti-foaming agents.
• acids in particular an organic lower monocarboxylic acid, e.g. Formic acid or acetic acid, buffer salts such as ammonium sulfate or sodium acetate, wetting agents, emulsifiers or anti-foaming agents.
• the liquor ratio is usually 1: 5 to 1:50; the dyeing time is 5 to 60 minutes.
• the process according to the invention is preferably carried out in circulation apparatus as follows: the unformed dyestuff or dyes are in the form of an aqueous suspension, a press cake or also in solid form, for example powder, in a batch vessel connected to the dyeing apparatus in about 50 ° to 150 ° C. hot water, for example dissolved or solubilized by means of a mixture of nonionic and anionic surfactant.
• the pH of the dye solution is adjusted to a value of 4 to 5.5.
• the dye solution if necessary after passing through a filter, is let into the dyeing apparatus, where the polyester material to be colored is present, for example in the form of a bobbin, such as muff, cheese, dyeing tree, or as an endless web.
• the substrate is preheated with steam.
• the dyebath is at a rate of approx. 1 ° C / minute to a temperature of 120 ° to 150 ° C, advantageously 125 ° to 135 ° C, heated. After the desired depth of color has been achieved or when the dye bath is completely exhausted - dyeing time approx.
• the hot liquor is cooled to such an extent that the goods can be removed from the liquor and the entrained liquor portion is reduced to less than 1% (e.g. by suction or centrifuging) the entire fleet can be reduced).
• Weighing the wet goods determines how much of the used dye liquor is removed and adds the corresponding amount of water and surfactant to the liquor remaining in the dye bath.
• the dye content of the remaining liquor is determined in the usual way, preferably photometrically, and the remaining liquor is then mixed with sufficient dye to achieve the liquor composition required for the next dyeing.
• the dyeing cycle described above can then be repeated.
• Example 1 In the metal container of a laboratory dyeing machine (Callebaut de Blicquy) 28.44 mg of the unformed dye of the formula
• a surfactant solution consisting of 42.7% reaction product of 1 mol of o-phenylphenol + 6 mol of ethylene oxide, 42.7% nonylphenol diglycol ether sulfate as a 40% aqueous solution , 14.2% water and 0.4% anti-foaming agent, dissolved at 98 ° C.
• the pH of the dye solution is adjusted to 4.6 to 5 by adding ammonium sulfate and formic acid, and then 10 g of polyester fabric (Crimplene®) are added to the liquor and the metal container is closed.
• the mixture is heated to 130 ° C. in the course of 6 minutes and this temperature is maintained for 30 minutes. Then it is cooled to a temperature below 100 ° and the substrate is removed from the liquor.
• the amount of entrained dye liquor (28.44 g) is determined by weighing the moist substrate; the residual dye content in the extracted dye liquor is determined photometrically (2.46 mg).
• polyester fabric Another 10 g of polyester fabric are added to this dyeing liquor and the dyeing process described above is repeated. This is done a total of 10 times.
• the colorations obtained are irrelevant and practically identical in color strength.
• the total degree of dye exhaustion after 10 dyeings was over 96%.
• Table 1 shows the amounts of water, dye and surfactant used or replaced and the photometrically determined relative color strength of the dyeings obtained, based on the first dyeing.
• Example 2 22.29 mg of the dried press cake of the dye of the formula are in the metal container of a laboratory dyeing machine (Callebaut de Blicquy)
• a surfactant solution (60% active substance), consisting of 42.7% reaction product of 1 mol of o-phenylphenol + 6 mol of ethylene oxide, 42.7% of nonylphenol diglycol ether sulfate as 40% aqueous solution, 14.2% water and 0.4% anti-foaming agent, dissolved at 98 ° C.
• the pH of the dye solution is adjusted to 4.6 to 5 by adding ammonium sulfate and formic acid, and 10 g of polyester fabric (Crimplene m )) are then added to the liquor and the metal container is closed.
• the mixture is heated to 130 ° C. in the course of 6 minutes and this temperature is maintained for 30 minutes. Then it is cooled to a temperature below 100 ° and the substrate is removed from the liquor.
• the amount of entrained dye liquor is determined by weighing the moist substrate; the residual dye content in the extracted dye liquor is determined photometrically (see Table 2).
• polyester fabric Another 10 g of polyester fabric are added to this dyeing liquor and the dyeing process described above is repeated. This is done a total of 10 times.
• Table 2 shows the amounts of water, dye and surfactant used or replaced, as well as the photometrically determined relative color strength of the dyeings obtained, based on the first dyeing.
• Examples 3-7 In Examples 3-7, polyester material (PES) was dyed using the same method and under the same conditions as in Example 2. Dye (dried press cake), amount of dye used, surfactant, surfactant concentration and number of colors can be found in Table 3.
• Example 8 The procedure of Example 2 is followed. 22.29 mg of the dye of the formula
• aqueous liquor containing 5 g / 1 of a carrier obtained by mixing in dodecylbenzenesulfonic acid, triethanolamine, diphenyl, uniperol EL, xylene, n-hexanol and ethylene glycol at 60 ° C, in 1.2.4-trichlorobenzene at 78 ° C .
• the pH had been adjusted (see Example 2), the temperature of the liquor was brought to 100 ° C. in about 1 minute.
• the polyester substrate was colored at 100 ° C for 60 minutes. You get a no matter red colored polyester material.
• Example 9 The procedure of Example 2 is repeated. 10 mg of the dye of the formula

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• 1986
  • 1986-05-07 EP EP86810208A patent/EP0204656A1/de not_active Withdrawn
  • 1986-05-09 US US06/861,676 patent/US4715863A/en not_active Expired - Fee Related
  • 1986-05-14 ZA ZA863556A patent/ZA863556B/xx unknown
  • 1986-05-14 JP JP61108726A patent/JPS61266684A/ja active Pending
  • 1986-05-14 KR KR1019860003762A patent/KR860009186A/ko not_active Application Discontinuation

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