EP0064030A1 - Mélange d'adjuvants de teinture et son utilisation dans la teinture de matériaux textiles synthétiques - Google Patents

Mélange d'adjuvants de teinture et son utilisation dans la teinture de matériaux textiles synthétiques Download PDF

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Publication number
EP0064030A1
EP0064030A1 EP82810168A EP82810168A EP0064030A1 EP 0064030 A1 EP0064030 A1 EP 0064030A1 EP 82810168 A EP82810168 A EP 82810168A EP 82810168 A EP82810168 A EP 82810168A EP 0064030 A1 EP0064030 A1 EP 0064030A1
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Prior art keywords
carbon atoms
component
mole
aid according
acid
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German (de)
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EP0064030B1 (fr
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Heinz Abel
Paul Dr. Schäfer
Hans-Ulrich Berendt
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Novartis AG
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Ciba Geigy AG
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    • 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
    • D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/6421—Compounds containing nitrile groups
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/60—Optical bleaching or brightening
    • D06L4/664—Preparations of optical brighteners; Optical brighteners in aerosol form; Physical treatment of optical brighteners

Definitions

  • the present invention relates to novel dyeing aids and their use in dyeing synthetic fiber materials, in particular polyester fibers.
  • Leveling agents for synthetic fiber materials often have the disadvantage that they retard the dye excessively and thus inevitably lead to a reduction in dispersion stability after the dyeing has ended and when the dye liquor has cooled.
  • the retained dye which is triggered by the mostly non-ionic leveling agents, leads to recrystallization and deposits when the dyeing liquor cools down, which in turn leads to inadequate rubbing fastness of the dyeings.
  • Dispersants that are used specifically for high-temperature conditions can prevent such recrystallization, but usually lead to a reduction in the color yield and also have no pronounced leveling effect.
  • auxiliary mixture according to the invention can additionally additionally to the components (A), (B) and (C) mentioned, the auxiliary mixture according to the invention can additionally
  • Siloxane-oxyalkylene copolymer or a mixture of these substances and / or
  • Components (A), (B), (C), (D) and (E) can be present as individual compounds or as mixtures.
  • Preferred auxiliary mixtures contain all of the components (A), (B), (C), (D) and (E) specified.
  • R advantageously represents the hydrocarbon radical of an unsaturated or preferably saturated aliphatic monoalcohol with 3 to 24 carbon atoms. These hydrocarbon radicals can be straight-chain or branched.
  • aliphatic saturated alcohols come, for example, propanol, isopropanol, n-butanol, isobutanol, sec. Butanol, tert. Butanol, n-amyl alcohol, iso amyl alcohol, tert.
  • Some of the Alfole representatives are Alfol (8-10), (10-14) and (16-18).
  • Unsaturated aliphatic alcohols are, for example, allyl alcohol, butenol, dodecenyl alcohol, hexadecenyl alcohol or oleyl alcohol.
  • the alcohol residues can be present alone or as mixtures.
  • the alcohol residues can optionally be mono-, di- or triethoxylated.
  • R can also be derived from a polyhydric aliphatic alcohol which has at least 2, advantageously 2 to 5 hydroxyl groups and preferably 2 to 9 carbon atoms, e.g. of alkylene diols with an alkylene radical of 2 to 6 carbon atoms, such as ethylene glycol, 1,3- or 1,2-propylene glycol or 1,5-pentanediol, and also glycerol, trimethylolethane, trimethylolpropane, erythritol, pentaerythritol, mannitol or sorbitol.
  • These polyhydric alcohols can also be etherified with 1 to 6 moles of ethylene oxide or propylene oxide or mixtures of these alkylene oxides.
  • R is preferably alkenyl or preferably alkyl each having 3 to 22 carbon atoms.
  • R is derived in particular from cyclopentanol, cyclohexanol, cyclododecanol, p-nonylcyclohexanol, hydroabietyl alcohol, or benzyl alcohol, phenylethyl alcohol or phenoxyethanol, the benzene nucleus also being derived from lower alkyl, e.g. Methyl, ethyl, isopropyl or lower alkoxy such as methoxy, ethoxy or isopropoxy or may be substituted by halogen.
  • lower alkyl and lower alkoxy generally represent groups or group components which have 1 to 5, in particular 1 to 3, carbon atoms, such as, for example, Methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or amyl or methoxy, ethoxy or isopropoxy.
  • Halogen in connection with all substituents means for example fluorine, bromine or preferably chlorine.
  • the compounds of the formulas (8), (11), (12), (13), (14) and (23) are particularly preferred.
  • the compounds of the formulas (1) to (25) are prepared in a manner known per se.
  • the preparation can preferably be carried out by reacting an alcohol of the formula R-OH, in which R has the meaning given, with acrylonitrile.
  • the reaction is preferably carried out in anhydrous media, e.g. in alcoholic media, in the presence of an alkali metal hydroxide or alcoholate or a quaternary base such as trimethyl-benzyl-ammonium hydroxide and at a temperature of 10 to 60 ° C.
  • the anionic surfactants of component (B) are preferably derivatives of alkyleneoxy adducts, such as e.g. addition products of alkylene oxides containing acidic, ether groups or preferably ester groups of inorganic or organic acids, especially ethylene oxide and / or propylene oxide or also styrene oxide onto aliphatic hydrocarbon radicals with a total of at least 4 carbon atoms, organic hydroxyl, carboxyl, amino and / or amido compounds or mixtures of these substances.
  • acidic ethers or esters can be used as free acids or as salts, e.g. Alkali metal, alkaline earth metal, ammonium or amine salts are present.
  • anionic surfactants are prepared by known methods, for example by adding at least 1 mol, preferably more than 1 mol, for example 2 to 60 mol, of ethylene oxide or propylene oxide to the organic compounds mentioned or, alternately, in any order of ethylene oxide or propylene oxide and then the addition products etherified or esterified and, if appropriate, the ethers or the esters converted into their salts.
  • the basic materials are higher fatty alcohols, that is to say alkanols or alkenols each having 8 to 22 carbon atoms, dihydric to hexavalent aliphatic alcohols having 2 to 9 carbon atoms, alicyclic alcohols, phenylphenols, benzylphenols, alkylphenols with one or more alkyl substituents, the one or more together
  • Highly suitable anionic surfactants of component (B) are acidic esters or their salts of a polyadduct of 2 to 50 moles of ethylene oxide with 1 mole Fatty alcohol with 8 to 22 carbon atoms or on 1 mol of a phenol which has at least one benzyl group, a phenyl group or preferably an alkyl group with at least 4 carbon atoms, such as, for example, benzylphenol, .dibenzylphenol, dibenzyl- (nonyl) phenol, o-phenylphenol, butylphenol , Tributylphenol, Octylphenol, Nonylphenol, Dodecylphenol or Pentadecylphenol, whereby these acidic esters can be used individually or as a mixture.
  • Preferred components (B) correspond to the formula wherein Y is alkyl or alkenyl with 8 to 22 carbon atoms, alkylphenyl with 4 to 16 carbon atoms in the alkyl part or o-phenylphenyl, X is the acid residue of an inorganic, oxygen-containing acid such as sulfuric acid or preferably phosphoric acid or the rest of an organic acid and m 2 to 40, preferably 2 to 15 mean.
  • the alkyl radical in the alkylphenyl is preferably in the para position.
  • the alkyl radicals in the alkylphenyl can be butyl, hexyl, n-octyl, n-nonyl, p-tert-octyl, p-iso-nonyl, decyl or dodecyl.
  • the alkyl radicals having 8 to 12 carbon atoms are preferred, in particular the octyl or nonyl radicals.
  • the fatty alcohols for the preparation of the anionic surfactants of formula (26) are e.g. those with 8 to 22, in particular 8 to 18, carbon atoms, such as octyl, decyl, lauryl, tridecyl, myristyl, cetyl, stearyl, oleyl, arachidyl or behenyl alcohol.
  • the acid residue X is derived, for example, from low molecular weight dicarboxylic acids, such as of maleic acid, succinic acid or sulfosuccinic acid, and is connected to the ethyleneoxy part of the molecule via an ester bridge.
  • X is derived from inorganic polybasic acids, such as sulfuric acid and in particular orthophosphoric acid.
  • the acid residue X can be in salt form, i.e. e.g. as an alkali metal, ammonium or amine salt.
  • salts are lithium, sodium, potassium, ammonium, trimethylamine, ethanolamine, diethanolamine or triethanolamine salts.
  • Particularly preferred components (B) are anionic surfactants of the formula wherein Y1 is octyl or nonyl, m l is 2 to 15 and X 1 is derived from sulfuric acid or preferably from o-phosphoric acid and the surfactants are present as free acids, sodium or ammonium salts.
  • anionic surfactants of the formula wherein Y1 is octyl or nonyl, m l is 2 to 15 and X 1 is derived from sulfuric acid or preferably from o-phosphoric acid and the surfactants are present as free acids, sodium or ammonium salts.
  • Y1 is octyl or nonyl
  • m l is 2 to 15
  • X 1 is derived from sulfuric acid or preferably from o-phosphoric acid and the surfactants are present as free acids, sodium or ammonium salts.
  • acidic phosphoric acid ester of the adduct of 5 to 12 moles of ethylene oxide with 1 mole of
  • the anionic surfactants of components (B) can be used alone or as mixtures with one another.
  • the nonionic surfactant (C) is advantageously a nonionic alkylene oxide adduct of 1 to 100 moles of alkylene oxide, e.g. Ethylene oxide and / or propylene oxide, on 1 mol of an aliphatic monoalcohol with at least 4 carbon atoms, a 3- to 6-valent aliphatic alcohol, a phenol which is optionally substituted by alkyl or phenyl or a fatty acid with 8 to 22 carbon atoms.
  • alkylene oxide e.g. Ethylene oxide and / or propylene oxide
  • the aliphatic monoalcohols for the production of the nonionic surfactants are e.g. water-insoluble monoalcohols having at least 4 carbon atoms, preferably 8 to 22 carbon atoms. These alcohols can be saturated or unsaturated and branched or straight-chain and can be used alone or in a mixture. Natural alcohols such as e.g. Myristyl alcohol, cetyl alcohol, stearyl alcohol or oleyl alcohol or synthetic alcohols, e.g.
  • Oxoalcohols such as, in particular, 2-ethylhexanol, furthermore trimethylhexanol, trimethylnonyl alcohol, hexadecyl alcohol or alfols, are reacted with the alkylene oxide.
  • alkylene oxides that can be reacted with alkylene oxide are 3- to 6-valent alkanols. These contain 3 to 6 carbon atoms and are in particular glycerol, trimethylolpropane, erythritol, mannitol, pentaerythritol and sorbitol.
  • the 3- to 6-valent alcohols are preferably reacted with propylene oxide or ethylene oxide or mixtures of these alkylene oxides.
  • Suitable optionally substituted phenols are, for example, phenol, o-phenylphenol or alkylphenols, the alkyl radical of which has 1 to 16, preferably 4 to 12, carbon atoms.
  • alkylphenols are p-cresol, butylphenol, tributylphenol, octylphenol, and especially nonylphenol.
  • the fatty acids preferably have 8 to 12 carbon atoms and can be saturated or unsaturated, e.g. capric, lauric, myristic, palmitic or stearic acid or decenic, dodecenic, tetradecenic, hexadecenic, oleic, linoleic, linolenic or preferably ricinoleic acid.
  • Suitable nonionic surfactants are addition products of 2 to 15 moles of ethylene oxide with 1 mole of fatty alcohol or fatty acid each with 8 to 22 carbon atoms or with 1 mole of alkylphenol with a total of 4 to 12 carbon atoms in the alkyl part or fatty acid dialkanolamides with 8 to 22 carbon atoms in the fatty acid residue.
  • the new dyeing aid can additionally contain an aliphatic alcohol as component (D) Contain 5 to 18 carbon atoms or a siloxane-oxyalkylene copolymer or preferably a mixture of these substances.
  • component (D) acts in particular as a foam suppressant.
  • the alcohols can be used as individual compounds or as mixtures with one another. They can be straight-chain or branched, saturated or unsaturated and should generally be liquid at room temperature. Examples include n-amyl alcohol, n-hexanol, trimethylhexanol, 2-ethyl-n-hexanol, octyl alcohol (octanol isomer mixture), nonyl alcohol, decyl alcohol, lauryl alcohol, tridecyl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol or oleyl alcohol, and also the alfoles such as e.g. Alfol (6-10), (8-10), (10-14), (12), (16) and (18). Alkanols having 5 to 10 carbon atoms are preferred, the 2-ethyl-n-hexanol being particularly suitable.
  • the organopolysiloxanes as the starting product for such adducts basically correspond to commercially available silicone oils, which are described in German specification 20 31 827. Among these silicone oils, polydimethylsiloxanes are of prime interest.
  • the siloxaneoxyalkylene copolymers in question as optional component (D) can be obtained, for example, from halogen-substituted organopolysiloxanes, especially polydimethylsiloxanes and alkali metal salts of polyoxyalkylene, e.g. Polyethylene and / or polypropylene glycols are produced.
  • siloxaneoxyalkylene copolymers are polyether siloxanes, which expediently have a cloud point at about 20 to 70 ° C., preferably 25 to 50 ° C.
  • the glycol content, consisting of oxyethylene groups or oxyethylene and oxypropylene groups, is advantageously from 35 to 85, preferably 40 to 75 percent by weight, based on the total weight of the polyether siloxane.
  • a preferred embodiment of the optional component (D) is accordingly a block polymer of a polydimethylsiloxane and ethylene oxide or a copolymer of ethylene and propylene oxide, which has a cloud point at 20 to 70 ° C, in particular 25 to 50 ° C.
  • Such block polymers or polyether siloxanes can by the likely formula in which q is 3 to 50, advantageously 3 to 25, r 2 or 3, s 0 to 15, t 1 to 25, x 1 3 to 10 and R 3 are alkyl having 1 to 4 carbon atoms, preferably methyl.
  • Such polyether siloxanes are described, for example, in German Patent Application 1,719,238 and in US Pat. Nos. 2,834,748, 3,389,160 and 3,505,377.
  • polyether siloxanes which can be used as optional component (D) correspond to the likely formula wherein R 4 and R 5 are each alkyl having 1 to 4 carbon atoms, preferably methyl, a '1 to 20, b' 2 to 20, c '2 to 50, d' 1 or 2, preferably 1, and m '2 to 5 mean and where C m ' H 2m' O d 'are preferably ethylene oxide groups or mixtures of ethylene oxide groups and propylene oxide groups.
  • Such siloxane compounds are described in German Patent Application 1,795,557.
  • the auxiliaries according to the invention can contain water as polar solvent (E) or a water-miscible organic solvent.
  • water-miscible organic solvents are aliphatic C 1 -C 4 alcohols such as methanol, ethanol; the propanols or isobutanol; Alkylene glycols such as ethylene glycol or propylene glycol; Monoalkyl ethers of glycols such as ethylene glycol monomethyl, ethyl or butyl ether and diethylene glycol monomethyl or ethyl ether; Ketones such as acetone, methyl ethyl ketone, cyclohexanone, diacetone alcohol; Ethers and acetals such as diisopropyl ether, diphenyl oxide, dioxane, tetrahydrofuran, also tetrahydrofurfuryl alcohol, pyridine, acet
  • the new dyeing aid mixtures can be prepared by simply stirring the above-mentioned components (A), (B), (C) and, if appropriate, (D) and / or (E), homogeneous clear mixtures being obtained which are stable in storage at room temperature.
  • the new formulations are used in particular as leveling agents in the dyeing of synthetic fiber materials. They increase the rate of diffusion of the dyes in the fibers and thereby accelerate the migration of the fibers when dyeing the synthetic fiber materials, preferably the linear polyester fibers.
  • the present invention accordingly also relates to a process for dyeing or optically brightening synthetic fiber material with cationic or disperse dyes or optical brighteners.
  • the process is characterized in that this material is dyed or optically brightened in the presence of the dyeing aid according to the invention. Disperse dyes are preferred.
  • the amounts used in which the dyeing aid according to the invention is added to the dye baths are between 0.5 and 6 percent by weight, preferably 2 and 4 percent by weight, based on the weight of the material to be dyed.
  • fiber material in particular textile material, which can be dyed or optically brightened in the presence of the new dyeing aid mixture
  • Cellulose ester fibers such as cellulose 2 1/2 acetate fibers and triacetate fibers
  • synthetic polyamide fibers e.g. those of 1-caprolactam, of adipic acid and hexamethylenediamine, of w-aminoundecanoic acid
  • aromatic polyamide fibers e.g. derived from poly (meta-phenylene-isophthalamide), mentioning polyacrylonitrile fibers, including modacrylic fibers, acid-modified polyester fibers, and especially linear polyester fibers.
  • Cellulose ester, polyamide and polyester fibers are preferably dyed with disperse dyes and polyacrylonitrile fibers, acid-modified polyester fibers and aromatic polyamide fibers preferably with cationic dyes.
  • Linear polyester fibers are to be understood as meaning synthetic fibers which are obtained, for example, by condensation of terephthalic acid with ethylene glycol or of isophthalic acid or terephthalic acid with 1,4-bis (hydroxymethyl) cyclohexane, and also copolymers of terephthalic and isophthalic acid and ethylene glycol.
  • the linear polyester used almost exclusively in the textile industry so far consists of terephthalic acid and ethylene glycol.
  • the acrylic fibers which can be dyed by the process according to the invention include the commercially available types of polymeric or mixed-polymer acrylonitrile.
  • Acid-modified polyester fibers are, for example, polycondensation products of terephthalic acid or isophthalic acid, ethylene glycol and 1,2- or 1,3-dihydroxy-3- (3-sodium sulfopropoxy) propane, 2,3-dimethylol-1- (sodium sulfopropoxy) butane, 2 , 2-bis- (3-sodium sulfo-propoxyphenyl) propane or 3,5-dicarboxy-benzenesulfonic acid or sulfonated terephthalic acid, sulfonated 4-methoxybenzenecarboxylic acid or sulfonated diphenyl-4,4'-dicarboxylic acid.
  • the fiber materials can also be used as a mixed fabric among themselves or with other fibers, e.g. Mixtures of polyacrylonitrile / polyester, polyamide / polyester, polyester / cotton, polyester / viscose and polyester / wool can be used.
  • the textile material to be dyed or optically brightened can be in various processing stages. Examples include: loose material, piece goods, such as knitted or woven fabrics, yarn in the form of a wrap or muff.
  • the latter can have winding densities of 200 to 600 g / dm 3 , in particular 400 to 450 g / dm 3 .
  • the cationic dyes suitable for the process according to the invention can belong to different classes of dyes.
  • these are the customary salts, for example chlorides, sulfates or metal halides, such as e.g. Zinc chloride double salts of cationic dyes, the cationic character of e.g. comes from a carbonium, oxonium, sulfonium or especially ammonium group.
  • chromophoric systems examples include azo dyes, especially monoazo or hydrazone dyes, diphenylmethane, triphenylmethane, methine or azomethine dyes, coumarin, ketonimine, cyanine, azine, xanthene, oxazine or thiazine dyes.
  • color salts of the phthalocyanine or anthraquinone series with an external onium group for example an alkylammonium or cycloammonium group, and benzo-1,2-pyran color salts which contain cycloammonium groups can also be used.
  • the disperse dyes to be used which are only sparingly soluble in water and are largely present in the dye liquor in the form of a fine dispersion, can belong to a wide variety of dye classes, for example the acridone, azo, anthraquinone, coumarin, methine, Perinone, naphthoquinoneimine, quinophthalone, styryl or nitro dyes.
  • Mixtures of cationic or disperse dyes can also be used according to the invention.
  • the new auxiliary mixtures can also be used for whitening undyed synthetic fiber materials with optical brighteners dispersed in water or cationic. Polyester fiber materials are preferably treated with optical brighteners dispersed in water.
  • optical brighteners can belong to any brightener class.
  • they are coumarins, triazolcoumarins, benzocoumarins, oxazines, pyrazines, pyrazolines, diphenylpyrazolines, stilbenes, styrylstilbenes, triazolylstilbenes, bisbenzoxazolylethylenes, stilbene-bis-benzoxazoles, phenylstilbenbenzoxazoles, thiophene-bis-benzoxazolezoleazolezoleazolezoleazolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezolezol
  • Mixtures of optical brighteners can also be used according to the invention.
  • the amount of dyes or optical brighteners to be added to the liquor depends on the desired color strength; In general, amounts of 0.01 to 10, preferably 0.02 to 5 percent by weight, based on the textile material used, have proven successful.
  • the auxiliaries to be used according to the invention can also be mixed with known carriers based on, for example, di- or trichlorobenzene, methyl- or ethylbenzene, o-phenylphenol, benzylphenol, diphenyl ether, Chlorodiphenyl, methyldiphenyl, cyclohexanone, acetophenone, alkylphenoxyethanol, mono-, di- or trichlorophenoxyethanol or propanol, pentachlorophenoxyethanol, alkylphenylbenzoate, or in particular based on diphenyl, methyldiphenyl ether, dibenzyl ether, methylbenzoate, butylbenzoate or phenylbenzoate or phenylbenzoate or phenylbenzoate or phenylbenzoate or phenylbenzoate or phenylbenzoate or phenylbenzoate or phenylbenzoate or phenyl
  • the carriers are preferably used in an amount of 0.5 g to 2 g / l of liquor or 5 to 30 percent by weight, based on the auxiliary preparation.
  • the dye baths or lightening liquors can contain, in addition to the dyes or optical brighteners, and the dyeing aid according to the invention, oligomer inhibitors, anti-foaming agents, wrinkle-free agents, retarders and preferably dispersants.
  • the dispersants are used primarily to achieve a good fine distribution of the disperse dyes.
  • the dispersants which are generally used for dyeing with disperse dyes are suitable.
  • the dispersants used are preferably sulfated or phosphated adducts of 15 to 100 moles of ethylene oxide or preferably propylene oxide with polyhydric aliphatic alcohols containing 2 to 6 carbon atoms, such as e.g. Ethylene glycol, glycerol or pentaerythritol or amines having 2 to 9 carbon atoms and having at least two amino groups or an amino group and a hydroxyl group and alkylsulfonates having 10 to 20 carbon atoms in the alkyl chain, alkylbenzenesulfonates having a straight-chain or branched alkyl chain having 8 to 20 carbon atoms in the alkyl chain, such as e.g.
  • Lignin sulfonates, polyphosphates and preferably formaldehyde condensation have proven to be particularly favorable as anionic dispersants
  • Products from aromatic sulfonic acids, formaldehyde and optionally monofunctional or bifunctional phenols such as, for example, from cresol, ⁇ -naphtholsulfonic acid and formaldehyde, from benzenesulfonic acid, formaldehyde and naphthalenesulfonic acid, from naphthalenesulfonic acid and formaldehyde or from naphthalenesulfonic acid ".Dihydroxydiphenylsulfone and preferably formaldehyde is disodium dinate Di- (6-sulfonaphthyl-2-) methane.
  • anionic dispersants can also be used.
  • the anionic dispersants are normally in the form of their alkali metal salts, ammonium salts or amine salts. These dispersants are preferably used in an amount of 0.1 to 5 g / 1 liquor.
  • the dye baths or lightening liquors can also contain conventional additives, suitably electrolytes such as salts, e.g. Sodium sulfate, ammonium sulfate, sodium or ammonium phosphates or polyphosphates, metal chlorides or nitrates such as calcium chloride, magnesium chloride or calcium nitrates, ammonium acetate or sodium acetate and / or acids, e.g. Mineral acids, such as sulfuric acid or phosphoric acid, or organic acids, suitably contain lower aliphatic carboxylic acids, such as formic, acetic or oxalic acid. The acids serve primarily to adjust the pH of the liquors used according to the invention, which is generally 4 to 6.5, preferably 4.5 to 6.
  • electrolytes such as salts, e.g. Sodium sulfate, ammonium sulfate, sodium or ammonium phosphates or polyphosphates, metal chlorides or nitrates such as calcium chloride,
  • the dyeing or lightening is advantageously carried out from an aqueous liquor using the exhaust process.
  • the liquor ratio can accordingly be chosen within a wide range, e.g. 1: 3 to 1: 100, preferably 1: 7 to 1:50.
  • the temperature at which the dyeing or lightening is at least 70 ° C. and as a rule it is not higher than 140 ° C. It is preferably in the range from 80 to 135 ° C.
  • Linear polyester fibers and cellulose triacetate fibers are preferably dyed by the so-called high temperature process in closed and expediently also pressure-resistant apparatus at temperatures of over 100 ° C, preferably between 110 and 135 ° C, and optionally under pressure.
  • Circulation devices such as cross-wound or tree dyeing machines, reel runners, nozzle or drum dyeing machines, muff dyeing machines, paddles or jiggers are suitable as closed vessels.
  • Cellulose-2.1 / 2-acetate fibers are preferably dyed at temperatures of 80-85 ° C., while polyamide fibers and polyacrylonitrile fibers are advantageously dyed at the boiling point (98 ° C.) of the aqueous bath.
  • the coloring of the aromatic polyamide fibers or acid-modified polyester fibers is preferably carried out at a temperature of 80 to 130 ° C.
  • the dyeing process according to the invention can be carried out by either briefly treating the material to be dyed first with the dyeing auxiliary and then dyeing it, or preferably treating it simultaneously with the auxiliary and the dye.
  • the material to be dyed is preferably allowed to run for 5 minutes at 60-80 ° C. in a bath which contains the dye, the auxiliary mixture and, if appropriate, further additives and is adjusted to a pH of 4.5 to 5.5, the temperature increases within 15 to 35 minutes to 110 to 135 ° C, preferably 130 ° C and the dye liquor 15 to 90 minutes, preferably 30 minutes, at this temperature.
  • the dyeings are completed by cooling the dye liquor to 60 to 80 ° C., rinsing the dyeings with water and, if appropriate, cleaning in a customary manner in an alkaline medium under reductive conditions. The dyeings are then rinsed again and dried. In the event of any use of carriers, the dyeings are advantageously heat-treated to improve the lightfastness, e.g. Thermal insulation, which is preferably carried out at 160 to 180 ° C and for 30 to 90 seconds.
  • Thermal insulation which is preferably carried out at 160 to 180 ° C and for 30 to 90 seconds.
  • the process according to the invention gives uniform and vivid colorations on synthetic fiber material, in particular on linear polyester fibers, which are also distinguished by good rub fastness and color yields.
  • the other fastness properties of the dyeings e.g. Light fastness are hardly influenced by the use of the auxiliary according to the invention.
  • the cyanoethylated compounds of the formulas (3) to (13) and (15) to (25) are also prepared in this way.
  • This substrate is then in 200 ml of a liquor heated to 60 ° C, which contains 0.4 g of dyeing aid (5) and 0.4 g of ammonium sulfate and the pH of which has been adjusted to pH 5.5 with 85% formic acid , brought in.
  • the liquor is then heated to 130 ° C. within 30 minutes and the substrate is treated at this temperature for 60 minutes.
  • the liquor is then cooled to 90 ° C., the substrate is rinsed and dried.
  • the previously undyed substrate now shows a high level of coloring and excellent levelness.
  • the dye liquor is then adjusted to pH 5.5 with formic acid and heated to 125 ° C. in the course of 30 minutes, after which the goods are dyed at this temperature for 30 minutes.
  • the dye is then rinsed and dried. A strong and rub-fast red coloring is obtained.
  • Example 6 The procedure described in Example 6 is followed, but using a liquor which instead of the optical brightener of the formula (110) has the same amount of an optical brightener of the formula or the formula contains, you also get level brilliant brightenings.

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  • Engineering & Computer Science (AREA)
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  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
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EP82810168A 1981-04-29 1982-04-23 Mélange d'adjuvants de teinture et son utilisation dans la teinture de matériaux textiles synthétiques Expired EP0064030B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH2782/81 1981-04-29
CH278281 1981-04-29

Publications (2)

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EP0064030A1 true EP0064030A1 (fr) 1982-11-03
EP0064030B1 EP0064030B1 (fr) 1985-01-16

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EP82810168A Expired EP0064030B1 (fr) 1981-04-29 1982-04-23 Mélange d'adjuvants de teinture et son utilisation dans la teinture de matériaux textiles synthétiques

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Country Link
US (1) US4453946A (fr)
EP (1) EP0064030B1 (fr)
JP (1) JPS57191376A (fr)
DE (1) DE3261917D1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0159010A3 (fr) * 1984-04-16 1987-08-19 Walter Thiel GmbH & Co. KG Procédé de teinture en continu de produits textiles contenant des fibres de polyester et/ou des mélanges de celles-ci avec des fibres cellulosiques ainsi que produits textiles obtenus selon ce procédé

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4661116A (en) * 1985-01-31 1987-04-28 Collins & Aikman Corporation Continuous dyeing of cationic dyeable polyester fibers
JP4390159B2 (ja) * 1995-11-17 2009-12-24 モーメンティブ・パフォーマンス・マテリアルズ・インク 化粧品組成物の蛍光による光沢付与法
BRPI0508910A (pt) * 2004-03-17 2007-08-14 Clariant Finance Bvi Ltd agente para pré-tratamento de têxteis lìquido

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3114588A (en) * 1962-02-26 1963-12-17 American Cyanamid Co Aryloxypropionitrile and dye mixtures and dyeing hydrophobic fibers therewith
DE1619425A1 (de) * 1965-08-11 1970-08-27 Ugine Kuhlmann Verfahren zum Faerben,Drucken,AEtzen oder optischen Aufhellen von Materialien auf Celluloseacetat-Basis
DE1619412A1 (de) * 1965-05-10 1970-09-24 Ugine Kuhlmann Verfahren zum Druck und zur Faerbung von Acrylfasern
US3531238A (en) * 1966-03-23 1970-09-29 Bayer Ag Process for the continuous dyeing or printing with basic dyestuffs of textile materials consisting of polyacrylonitrile
FR2088522A1 (en) * 1970-05-12 1972-01-07 Ici Ltd Antifoam compsn - based on siloxane/oxyalkylene copolymers - soluble in cold water and contg finely divided silica
US3819327A (en) * 1971-06-30 1974-06-25 Meisei Chemical Works Ltd Method of printing synthetic fibers
DE2500882A1 (de) * 1974-01-18 1975-07-24 Ciba Geigy Ag Verfahren zum faerben von acrylfasern
DE2409437A1 (de) * 1971-11-16 1975-09-11 Albright & Wilson Verfahren zum selektiven faerben von mischfasern oder mischfasertextilien
DE2410481A1 (de) * 1974-03-05 1975-09-11 Albright & Wilson Verfahren zum faerben von modacrylfasern
DE2638833A1 (de) * 1976-08-28 1978-03-09 Bayer Ag Verfahren zum kontinuierlichen faerben bzw. bedrucken von fasermaterialien aus natuerlichen und/oder synthetischen polyamiden

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1034782A (en) * 1962-01-24 1966-07-06 Union Carbide Corp Organosilicon compositions
DE2444102C2 (de) * 1974-09-14 1978-12-21 Basf Ag, 6700 Ludwigshafen Verfahren zum Färben von Polyesterfasern

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3114588A (en) * 1962-02-26 1963-12-17 American Cyanamid Co Aryloxypropionitrile and dye mixtures and dyeing hydrophobic fibers therewith
DE1619412A1 (de) * 1965-05-10 1970-09-24 Ugine Kuhlmann Verfahren zum Druck und zur Faerbung von Acrylfasern
DE1619425A1 (de) * 1965-08-11 1970-08-27 Ugine Kuhlmann Verfahren zum Faerben,Drucken,AEtzen oder optischen Aufhellen von Materialien auf Celluloseacetat-Basis
US3531238A (en) * 1966-03-23 1970-09-29 Bayer Ag Process for the continuous dyeing or printing with basic dyestuffs of textile materials consisting of polyacrylonitrile
FR2088522A1 (en) * 1970-05-12 1972-01-07 Ici Ltd Antifoam compsn - based on siloxane/oxyalkylene copolymers - soluble in cold water and contg finely divided silica
US3819327A (en) * 1971-06-30 1974-06-25 Meisei Chemical Works Ltd Method of printing synthetic fibers
DE2409437A1 (de) * 1971-11-16 1975-09-11 Albright & Wilson Verfahren zum selektiven faerben von mischfasern oder mischfasertextilien
DE2500882A1 (de) * 1974-01-18 1975-07-24 Ciba Geigy Ag Verfahren zum faerben von acrylfasern
DE2410481A1 (de) * 1974-03-05 1975-09-11 Albright & Wilson Verfahren zum faerben von modacrylfasern
DE2638833A1 (de) * 1976-08-28 1978-03-09 Bayer Ag Verfahren zum kontinuierlichen faerben bzw. bedrucken von fasermaterialien aus natuerlichen und/oder synthetischen polyamiden

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0159010A3 (fr) * 1984-04-16 1987-08-19 Walter Thiel GmbH & Co. KG Procédé de teinture en continu de produits textiles contenant des fibres de polyester et/ou des mélanges de celles-ci avec des fibres cellulosiques ainsi que produits textiles obtenus selon ce procédé

Also Published As

Publication number Publication date
US4453946A (en) 1984-06-12
EP0064030B1 (fr) 1985-01-16
DE3261917D1 (en) 1985-02-28
JPS57191376A (en) 1982-11-25

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