EP0499090B1 - Procédé de teinture de textiles en polyester et en contenant - Google Patents

Procédé de teinture de textiles en polyester et en contenant Download PDF

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Publication number
EP0499090B1
EP0499090B1 EP92101415A EP92101415A EP0499090B1 EP 0499090 B1 EP0499090 B1 EP 0499090B1 EP 92101415 A EP92101415 A EP 92101415A EP 92101415 A EP92101415 A EP 92101415A EP 0499090 B1 EP0499090 B1 EP 0499090B1
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EP
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Prior art keywords
hydrogen
carbon atoms
chlorine
bromine
nitro
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Expired - Lifetime
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EP92101415A
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German (de)
English (en)
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EP0499090A1 (fr
Inventor
Ulrich Dr. Bühler
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Hoechst Mitsubishi Kasei Co Ltd
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Hoechst Mitsubishi Kasei Co Ltd
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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
    • 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
    • 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
    • D06P3/82—Textiles which contain different kinds of fibres
    • D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
    • D06P3/8214—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing ester and amide groups
    • 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
    • D06P3/82—Textiles which contain different kinds of fibres
    • D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
    • D06P3/8223—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups
    • D06P3/8228—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using one kind of dye
    • D06P3/8233—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using one kind of dye using dispersed dyes
    • 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

Definitions

  • the present invention relates to a process for HT dyeing polyester or polyester-containing textile materials.
  • polyester or polyester-containing textile materials are dyed with disperse dyes from an aqueous dyebath under HT conditions in a temperature range from 120 to 140 ° C at pH values from 4 to 6, since the disperse dyes are partially or completely destroyed at higher pH values. At higher pH values, there is a loss of color strength and color deviations during dyeing and the dyeings are not reproducible.
  • the polyester fiber is normally subjected to an alkaline rinse treatment in a separate step before dyeing, in order to remove auxiliaries which have been used in the weaving or spinning of the fibers. These tools are e.g. Lubricants or sizing agents which, if present, would make it difficult or impossible to dye the polyester fiber evenly.
  • the alkaline treatment is also carried out in order to destroy oligomers of the polyester fiber which have emerged from the inside of the fiber during the dyeing process and make the dyeing appear uneven, and to keep it in the aqueous dyeing liquor.
  • This alkaline rinsing treatment is advantageously carried out at an elevated temperature.
  • alkaline pretreatment and dyeing it has always been the goal to combine both processes into a one-bath rinsing and dyeing process.
  • processes have to be developed which give reproducible dyeings in the aqueous dye bath at pH 8 to pH 11.
  • Polyester-cellulose or polyester-polyamide blended fabrics are usually dyed with dispersing or reactive dyes from an aqueous dyebath in two dyeing steps.
  • the disperse dyes are applied to the polyester portion at pH 4 to 6, the reactive dyes to the cellulose or polyamide portion in the pH range between pH 11 and 13.
  • the goal in the past was a to develop a single bath application process for both dye classes.
  • a search has been made for reactive dyes which can already be dyed at pH values between 8 and 11, and processes were also required here which ensure that under these conditions the polyester content can be dyed reproducibly with disperse dyes.
  • DE-A-39 38 631 describes a method in which disperse dyes in the pH range between pH 8 and 10 in the presence of at least one amino acid which is optionally substituted on nitrogen and / or an alkali metal salt, one optionally on Nitrogen-substituted amino acid can be colored.
  • a preferred radical X2 in the dyes of the general formula I is hydrogen.
  • Preferred radicals X3 are nitro and alkylsulfonyl with 1 to 4 carbon atoms or chlorine and bromine if X1 simultaneously denotes nitro or methylsulfonyl, where, if X1 is methylsulfonyl, X3 cannot simultaneously be alkylsulfonyl with 1 to 4 C atoms and vice versa .
  • Preferred radicals R are hydrogen, allyl or alkyl having 1 to 4 carbon atoms.
  • Particularly preferred dyes of the general formula Ia are those in which X1 is nitro or methylsulfonyl, X3 nitro or alkylsulfonyl having 1 to 4 carbon atoms and Y4 is hydrogen, methyl, ethyl, methoxy or ethoxy, where either X1 or X3 is nitro.
  • Very particularly preferred dyes of the general formula Ia are those in which X1 is nitro, X3 nitro, X4 is hydrogen, chlorine or bromine and Y4 is hydrogen.
  • Particularly preferred dyes of the general formula Ib are those in which X1 is chlorine, bromine, nitro or methylsulfonyl, X2 is hydrogen, X3 is nitro or alkylsulfonyl having 1 to 4 C atoms, X4 is hydrogen and R is alkyl having 1 to 4 C atoms, where, when X1 is methylsulfonyl, X3 cannot simultaneously be alkylsulfonyl with 1 to 4 carbon atoms and vice versa.
  • a very particularly preferred dye of the general formula Ib is that in which X1 is chlorine, X3 nitro and X2, X3 and R are hydrogen.
  • Particularly preferred dyes of the general formula Ic are those in which X1 chlorine, bromine, nitro or methylsulfonyl, X2 hydrogen, X3 nitro or alkylsulfonyl having 1 to 4 carbon atoms, X4 hydrogen, chlorine or bromine, Y1 hydrogen or methyl and R allyl or mean alkyl with 1 to 4 carbon atoms and in particular hydrogen, where if X 1 is methylsulfonyl, X 3 cannot simultaneously be alkyl sulfonyl with 1 to 4 carbon atoms and vice versa.
  • the dyes of general formula I are known and e.g. described in DE-A-22 12 755 and in DE-A-31 63 272.
  • the HT process according to the invention is preferably carried out in a dyeing autoclave.
  • polyesters to be colored by the process according to the invention are in particular those based on polyethylene glycol terephthalates.
  • Textile materials containing polyester are mixtures of polyester and polyamides and in particular polyester / cellulose blended fabrics.
  • the dyes or dye mixtures are used in a fine distribution.
  • the fine distribution of the dyes is carried out in a manner known per se by adding the dye obtained in production together with dispersing agents in a liquid medium, preferably in water, and the mixture is exposed to the action of shear forces, the originally present dye particles being mechanically crushed to such an extent that an optimal specific surface is achieved and the sedimentation of the dye is as low as possible.
  • the particle sizes of the dyes are generally between 0.5 and 5 »m, preferably about 1» m.
  • the dispersants used in the grinding process can be nonionic or anionic.
  • Nonionic dispersants are e.g. Reaction products of alkylene oxides, e.g. Ethylene or propylene oxide with alkylatable compounds such as e.g. Fatty alcohols, fatty amines, fatty acids, phenols, alkylphenols and carboxamides.
  • Anionic dispersants are, for example, lignin sulfonates, alkyl or alkylaryl sulfonates or alkyl aryl polyglycol ether sulfonates.
  • the dye preparations thus obtained are said to be pourable for most applications.
  • the dye and dispersant content is therefore limited in these cases.
  • the dispersions are adjusted to a dye content of up to 50% by weight and a dispersant content of up to about 25%.
  • the dye content is usually not below 15% by weight.
  • the dispersions can also contain other auxiliaries, e.g. those that act as oxidizing agents, e.g. Sodium m-nitrobenzenesulfonate or fungicidal agents such as e.g. Sodium o-phenyl phenolate and sodium pentachlorophenolate.
  • auxiliaries e.g. those that act as oxidizing agents, e.g. Sodium m-nitrobenzenesulfonate or fungicidal agents such as e.g. Sodium o-phenyl phenolate and sodium pentachlorophenolate.
  • Powder settings are preferred for certain areas of application. These powders contain the dye or dye mixture, dispersants and other auxiliaries, such as wetting, oxidizing, preserving and dedusting agents.
  • a preferred method of manufacturing powdered dye formulations is to withdraw the liquid from the liquid dye dispersions described above, e.g. by vacuum drying, freeze drying, by drying on drum dryers, but preferably also by spray drying.
  • the required amounts of the dye settings which have been prepared according to the above information are diluted with the dyeing medium, preferably with water, to such an extent that a liquor ratio of 1: 5 to 1:50 results for the dyeing.
  • further dyeing aids such as dispersing, wetting and fixing aids, are generally added to the liquors.
  • the required pH of the dye liquor is determined before or during the dyeing by adding bases such as alkali hydroxides, e.g. aqueous sodium hydroxide solution, alkali hydrogen carbonates, e.g. Sodium bicarbonate or alkali carbonates e.g. Soda, discontinued.
  • bases such as alkali hydroxides, e.g. aqueous sodium hydroxide solution, alkali hydrogen carbonates, e.g. Sodium bicarbonate or alkali carbonates e.g. Soda, discontinued.
  • a preferred pH is pH 9-10.
  • buffer substances are preferably added, as described, for example, in JSDC, 77 (1979) p. 47 or JSDC 79 (1981), p. 115.
  • Particularly suitable buffer substances are those which have the greatest buffering action in the pH range between 9 and 11.
  • Suitable buffer systems are, for example, acetic acid / sodium pyrophosphate, boric acid / borax, sodium dihydrogen phosphate / disodium hydrogen phosphate, phosphoric acid / succinic acid / boric acid or combinations of organic phosphorus compounds with polycarboxylic acids.
  • the amounts of buffer system used are preferably between 0.5 and 10 g / l.
  • 1.5 g of a 20% liquid preparation of the dye of formula II are in a dyeing autoclave in a dyeing liquor consisting of 2 l of water, 2 g of a dyeing aid based on formaldehyde condensation product and 5 g of a buffer substance, which is a mixture of an organic phosphorus compound and a polycarboxylic acid, at 130 ° C for 100 g of a fabric dyed from polyethylene terephthalate after the pH of the dye liquor had previously been set to 9 with aqueous sodium hydroxide solution. The dyeing is then reductively cleaned, rinsed and dried. This gives an orange color.
  • the dyeing is repeated, 4 g of sodium acetate now being added as the buffer substance and the pH of the dyeing liquor being adjusted to 4.5 with acetic acid.
  • the resulting orange coloration serves as a reference in a colorimetric comparison with the pH 9 coloration.
  • the colorimetric values of the pH9 staining are: color strength: 101.6%, ⁇ H 0.02, ⁇ C - 0.33, ie both colors are practically identical in color.
  • the dye has practically not decomposed at pH 9.
  • the dye of the formula II in Example 1 is replaced by 4 g of a 10% strength liquid preparation of the dye of the formula III
  • the dye liquor is buffered with a mixture of 3.6 ml phosphoric acid, 4 g succinic acid and 4 g boric acid and the pH of the dye liquor is adjusted to 10 with aqueous sodium hydroxide solution, a dark brown color is obtained.
  • This coloration shows the following colorimetric values in comparison to a coloration carried out at pH 4.5: color strength: 101.9%, ⁇ H-0.59, ⁇ C 0.02.
  • the dye has practically not decomposed at an elevated pH.
  • the dye of formula II in Example 1 is replaced by 3 g of a 10% liquid setting of the dye of formula IV and dyeing at pH 9.5, the resulting yellow-brown coloration shows the following colorimetric values compared to that obtained at pH 4.5: color strength: 102%, ⁇ H - 0.16, ⁇ C 0.1 and is thus also almost identical in color .

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Coloring (AREA)

Claims (10)

  1. Procédé pour la teinture HT de polyesters ou de matières textiles contenant du polyester, à un pH de 8 à 11, caractérisé en ce qu'on utilise un ou plusieurs colorants monoazoïques de formule générale I
    Figure imgb0019
     dans laquelle
    X¹   représente l'hydrogène, les chlore, brome, nitro ou alkylsulfonyle comportant de 1 à 4 atomes de carbone,
    X²   représente l'hydrogène, les chlore ou brome,
    X³   représente l'hydrogène, les chlore, brome, nitro ou alkylsulfonyle comportant de 1 à 4 atomes de carbone,
    X⁴   représente l'hydrogène, les chlore ou brome,
    Y¹   représente l'hydrogène ou le méthyle,
    Y²   représente l'hydrogène,
    Y³   représente l'hydrogène,
    Y⁴   représente l'hydrogène, les alkyle comportant de 1 à 4 atomes de carbone ou alcoxy comportant de 1 à 4 atomes de carbone et
    R   représente l'hydrogène, les allyle ou alkyle comportant de 1 à 6 atomes de carbone, qui peuvent être éventuellement substitués par un alcoxy comportant de 1 à 4 atomes de carbone,
    Y¹, au lieu de l'hydrogène ou du méthyle, et Y², au lieu de l'hydrogène, pouvant aussi former, ensemble avec le noyau de benzène qui les porte, un radical naphtyle, et Y² et Y³, au lieu de l'hydrogène, ensemble, pourvant former une liaison directe.
  2. Procédé selon la revendication 1, caractérisé en ce que dans la formule générale I, X² représente l'hydrogène, X³ représente les nitro ou alkylsulfonyle comportant de 1 à 4 atomes de carbone ou bien les chlore ou brome, si X¹ représente simultanément les nitro ou méthylsulfonyle, ainsi que R représente l'hydrogène, les allyle ou alkyle comportant de 1 à 4 atomes de carbone, si X¹ est le méthylsulfonyle, X³ ne pouvant pas être simultanément un alkylsulfonyle comportant de 1 à 4 atomes de carbone et inversement.
  3. Procédé selon la revendication 1, caractérisé en ce qu'on utilise un ou plusieurs colorants monoazoïques de formule générale Ia,
    Figure imgb0020
     dans laquelle
    X¹   représente les chlore, brome, nitro ou alkylsulfonyle comportant de 1 à 4 atomes de carbone,
    X³   représente les chlore, brome, nitro ou alkylsulfonyle comportant de 1 à 4 atomes de carbone,
    X⁴   représente l'hydrogène, les chlore ou brome, et
    Y⁴   représente l'hydrogène, les alkyle comportant de 1 à 4 atomes de carbone ou alcoxy comportant de 1 à 4 atomes de carbone
    X¹ et X³ ne pouvant pas représenter simultanément un alkylsulfonyle comportant de 1 à 4 atomes de carbone.
  4. Procédé selon la revendication 3, caractérisé en ce que dans la formule générale Ia, X¹ représente un nitro, X³ représente un nitro, X⁴ l'hydrogène, les chlore ou brome et X⁴ représente l'hydrogène.
  5. Procédé selon la revendication 1, caractérisé en ce qu'on utilise un ou plusieurs colorants monoazoïques de formule générale Ib,
    Figure imgb0021
     dans laquelle
    X¹   représente l'hydrogène, les chlore, brome, nitro ou alkylsulfonyle comportant de 1 à 4 atomes de carbone,
    X²   représente l'hydrogène, les chlore ou brome,
    X³   représente les chlore, brome, nitro ou alkylsulfonyle comportant de 1 à 4 atomes de carbone,
    X⁴   représente l'hydrogène, les chlore ou brome, et
    R   représente l'hydrogène, les allyle, alkyle comportant de 1 à 6 atomes de carbone, qui peut être éventuellement substitué par un alcoxy comportant de 1 à 4 atomes de carbone,
    X¹ et X³ ne pouvant pas représenter simultanément un alkylsulfonyle comportant de 1 à 4 atomes de carbone.
  6. Procédé selon la revendication 5, caractérisé en ce que dans la formule générale Ib, X¹ représente le chlore, X³ représente un nitro et X², X³ et R représentent l'hydrogène.
  7. Procédé selon la revendication 1, caractérisé en ce qu'on utilise un ou plusieurs colorants monoazoïques de formule générale Ic,
    Figure imgb0022
     dans laquelle
    X¹   représente l'hydrogène, les chlore, brome, nitro ou alkylsulfonyle comportant de 1 à 4 atomes de carbone,
    X²   représente l'hydrogène, les chlore ou brome,
    X³   représente les chlore, brome nitro ou alkylsulfonyle comportant de 1 à 4 atomes de carbone,
    X⁴   représente l'hydrogène, les chlore ou brome,
    Y¹   représente l'hydrogène ou le méthyle, et
    R   représente l'hydrogène, les allyle ou alkyle comportant de 1 à 6 atomes de carbone, qui peut être éventuellement substitué par un alcoxy comportant de 1 à 4 atomes de carbone,
    X¹ et X³ ne pouvant pas représenter simultanément un alkylsulfonyle comportant de 1 à 4 atomes de carbone.
  8. Procédé selon la revendication 7, caractérisé en ce que dans la formule générale Ic
    X¹   représente les chlore, brome, nitro ou méthylsulfonyle,
    X²   représente l'hydrogène,
    X³   représente les nitro ou alkylsulfonyle comportant de 1 à 4 atomes de carbone,
    X⁴   représente l'hydrogène, les chlore ou brome,
    Y¹   représente l'hydrogène ou le méthyle, et
    R   représente les allyle ou alkyle comportant de 1 à 6 atomes de carbone, et notamment l'hydrogène,
    si X¹ est le méthylsulfonyle, X³ ne pouvant pas être simultanément un alkylsulfonyle comportant de 1 à 4 atomes de carbone et inversement.
  9. Procédé selon l'une ou plusieurs des revendications 1 à 8, caractérisé en ce qu'on effectue la teinture à un pH de 9 à 10.
  10. Procédé selon l'une ou plusieurs des revendications 1 à 9, caractérisé en ce qu'on effectue la teinture en présence d'une ou de plusieurs substances tampons, qui tamponnent dans le domaine de pH chaque fois utilisé.
EP92101415A 1991-02-15 1992-01-29 Procédé de teinture de textiles en polyester et en contenant Expired - Lifetime EP0499090B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4104655 1991-02-15
DE4104655A DE4104655A1 (de) 1991-02-15 1991-02-15 Verfahren zum faerben von polyester und polyesterhaltigen textilmaterialien

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EP0499090A1 EP0499090A1 (fr) 1992-08-19
EP0499090B1 true EP0499090B1 (fr) 1995-04-05

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EP92101415A Expired - Lifetime EP0499090B1 (fr) 1991-02-15 1992-01-29 Procédé de teinture de textiles en polyester et en contenant

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US (1) US5244471A (fr)
EP (1) EP0499090B1 (fr)
JP (1) JPH04333677A (fr)
DE (2) DE4104655A1 (fr)
ES (1) ES2070533T3 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4106323A1 (de) * 1991-02-28 1992-09-03 Cassella Ag Verfahren zum faerben von polyester und polyesterhaltigen textilmaterialien
DE4136654A1 (de) * 1991-11-07 1993-05-13 Cassella Ag Verfahren zum faerben von polyester und polyesterhaltigen textilmaterialien
PL169333B1 (pl) * 1992-05-26 1996-07-31 Inst Chemii Przemyslowej Im Pr Sposób wytwarzania nowych reaktywnych barwników karbazolowych PL
EP0661351B1 (fr) * 1994-01-03 1999-11-10 DyStar Textilfarben GmbH & Co. Deutschland KG Colorants monoazocarbazoliques
DE4422293A1 (de) 1994-06-25 1996-01-04 Cassella Ag Monoazoindolfarbstoffe
WO1996018767A1 (fr) * 1994-12-13 1996-06-20 Hoechst Celanese Corporation Procede de teinture des melanges polyester-coton
DE4446943A1 (de) * 1994-12-28 1996-07-04 Cassella Ag Verfahren zum Färben von Polyester und polyesterhaltigen Textilmaterialien
WO2011052007A1 (fr) 2009-10-28 2011-05-05 トヨタ自動車株式会社 Dispositif de commande de frein

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1185413A (fr) * 1956-02-16 1959-07-31 Hoechst Ag Procédé d'impression de matières textiles
DE2212755C2 (de) * 1972-03-16 1982-12-02 Cassella Ag, 6000 Frankfurt Verfahren zum Färben und Bedrucken von synthetischen hydrophoben Materialien
US3984199A (en) * 1972-03-16 1976-10-05 Cassella Farbwerke Mainkur Aktiengesellschaft Water-insoluble monoazo dyestuffs
DE3004653A1 (de) * 1980-02-08 1981-08-13 Basf Ag, 6700 Ludwigshafen Marineblaue farbstoffmischungen
DE3007518A1 (de) * 1980-02-28 1981-09-17 Cassella Ag, 6000 Frankfurt Wasserunloesliche azofarbstoffe, verfahren zu ihrer herstellung und verwendung zum faerben und bedrucken von synthetischem, hydrophobem fasermaterial
JPS58160356A (ja) * 1982-03-18 1983-09-22 Sumitomo Chem Co Ltd モノアゾ染料の製法
US5019133A (en) * 1988-11-25 1991-05-28 Mitsubishi Kasei Corporation Method for dyeing polyester-containing fibers in an alkaline dyeing bath and dyeing assistant, an amino-acid compound
DE4106323A1 (de) * 1991-02-28 1992-09-03 Cassella Ag Verfahren zum faerben von polyester und polyesterhaltigen textilmaterialien

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DE59201801D1 (de) 1995-05-11
JPH04333677A (ja) 1992-11-20
DE4104655A1 (de) 1992-08-20
EP0499090A1 (fr) 1992-08-19
ES2070533T3 (es) 1995-06-01
US5244471A (en) 1993-09-14

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