EP0601971A1 - Procédé de teinture ou d'impression par trichromie - Google Patents

Procédé de teinture ou d'impression par trichromie Download PDF

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Publication number
EP0601971A1
EP0601971A1 EP93810813A EP93810813A EP0601971A1 EP 0601971 A1 EP0601971 A1 EP 0601971A1 EP 93810813 A EP93810813 A EP 93810813A EP 93810813 A EP93810813 A EP 93810813A EP 0601971 A1 EP0601971 A1 EP 0601971A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
dye
formula
hydrogen
alkoxy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP93810813A
Other languages
German (de)
English (en)
Other versions
EP0601971B1 (fr
Inventor
Jean-Marie Dr. Adam
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Schweiz AG
Original Assignee
Ciba Geigy AG
Ciba Spezialitaetenchemie Holding AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ciba Geigy AG, Ciba Spezialitaetenchemie Holding AG filed Critical Ciba Geigy AG
Publication of EP0601971A1 publication Critical patent/EP0601971A1/fr
Application granted granted Critical
Publication of EP0601971B1 publication Critical patent/EP0601971B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02Material containing basic nitrogen
    • D06P3/04Material containing basic nitrogen containing amide groups
    • D06P3/14Wool
    • D06P3/16Wool using acid dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02Material containing basic nitrogen
    • D06P3/04Material containing basic nitrogen containing amide groups
    • D06P3/24Polyamides; Polyurethanes
    • D06P3/241Polyamides; Polyurethanes using acid dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/82Textiles which contain different kinds of fibres
    • D06P3/8204Textiles which contain different kinds of fibres fibres of different chemical nature
    • D06P3/8209Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing amide groups
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916Natural fiber dyeing
    • Y10S8/917Wool or silk
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92Synthetic fiber dyeing
    • Y10S8/924Polyamide fiber

Definitions

  • the present invention relates to a process for trichromatic dyeing or printing of natural and synthetic polyamide fiber materials with at least one blue-coloring, sulfo-containing anthraquinone dye, at least one red-dyeing azo dye and at least one yellow-colored or orange-dyeing azo dye.
  • the object underlying the present invention was to find a method for dyeing or printing natural and synthetic polyamide fiber materials with dyes suitable for combination according to the trichromatic principle.
  • the dyeings obtained in this way fulfill the tasks set.
  • the dyeings obtained are distinguished by a uniform color structure with constant shade in different concentrations and good combinability.
  • the present invention relates to a process for trichromatic dyeing or printing of natural or synthetic polyamide fiber materials, which is characterized in that at least one blue-coloring anthraquinone dye of the formula wherein R1, R2, R3 and R4 are independently hydrogen or C1-C6 alkyl, the sum of the carbon atoms of the radicals R1, R2, R3 and R4 being 4, 5 or 6 and the sulfo group in the anthraquinone dye of the formula (1) being bonded in the 6 or 7 position, together with at least one red-coloring dye of the formula wherein R5 is phenyl or cyclohexyl and R6 is C1-C4-alkyl, or the radicals R5 and R6 together with the nitrogen atom connecting them form an azepinyl ring, and at least one of the yellow or orange-colored dyes of the formulas (3), (4) and ( 5) wherein R7, R8 and R10 are independently hydrogen, C1-C4-alkyl, C
  • Trichromatic is to be understood as the additive color mixture of suitably selected yellow or orange, red and blue coloring dyes, with which any desired shade of the visible color spectrum can be adjusted by a suitable choice of the proportions of the dyes.
  • C1-C6 alkyl for R1, R2, R3 and R4 in formula (1) e.g. Methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl and straight-chain or branched pentyl or hexyl are also suitable.
  • the C1-C4 alkyl radicals are preferred.
  • the anthraquinone dyes of the formula (1) are generally used as mixtures of isomers, the individual isomers differing only in the sulfo group bonded in the 6- or 7-position; however, the individual isomers can also be used as individual dyes.
  • R6, R7, R8, R9, R10, B1, B2, E1, X, W2 and W3 are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl into consideration.
  • R7, R8, R10, B1, B2, E1 and W2 for example methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy or tert-butoxy.
  • C2-C4-alkanoylamino for example acetylamino, propionylamino or butyrylamino, especially acetylamino.
  • R7, R8, R10 and W2 for example fluorine or bromine and especially chlorine come into consideration.
  • C2-C4-hydroxyalkyl radical for X is a straight-chain or branched hydroxyalkyl radical, such as the ⁇ -hydroxyethyl, ⁇ -hydroxypropyl, ⁇ -hydroxybutyl or the ⁇ -ethyl- ⁇ -hydroxyethyl radical.
  • W4 is a C1-C8 alkyl residue, it is e.g. methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, and straight-chain or branched pentyl, hexyl, heptyl or octyl.
  • W1 as phenylsulfonyl and W3 as phenyl can be unsubstituted in the phenyl ring or by C1-C4-alkyl, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl, C1-C4-alkoxy, such as methoxy , Ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy or tert-butoxy, or by halogen, such as Fluorine, bromine or especially chlorine, may be substituted.
  • C1-C4-alkyl such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl
  • C1-C4-alkoxy such as methoxy , Ethoxy, propoxy, isopropoxy, butoxy,
  • the anthraquinone dyes of the formula (1) used are preferably those in which R2 and R3 are independently methyl or ethyl and R4 is hydrogen or methyl.
  • the radical R 1 in the anthraquinone dye of the formula (1) is preferably isopropyl or sec-butyl, in particular isopropyl.
  • Anthraquinone dyes of the formula (1) in which R1 is isopropyl, R2 and R3 are independently methyl or ethyl and R4 is hydrogen or methyl are particularly preferred for the process according to the invention.
  • the sum of the carbon atoms of the radicals R1, R2, R3 and R4 in the anthraquinone dye of the formula (1) is preferably the number 5.
  • Anthraquinone dyes of the formula (1) in which R1 is isopropyl, R2 and R3 are methyl and R4 is hydrogen are very particularly preferred.
  • a dye of the formula is preferably used as the red-coloring dye of the formula (2) or in particular a dye of the formula (6) or (7) and preferably a dye of the formula (6).
  • the yellow or orange coloring dyes of the formula (3) are preferably dyes containing sulfo groups.
  • yellow or orange coloring dyes of the formula (4) are preferably used in which B1 and B2 are independently C1-C Alkyl-alkyl or C1-C4-alkoxy, E1 is hydrogen and X is C1-C4-alkyl, especially the dye of formula
  • yellow or orange coloring dyes of the formula (5) are preferably used in which W1 phenylsulfonyl, W2 hydrogen, halogen or C1-C4-alkyl, W3 optionally substituted by C1-C4-alkyl, C1-C4-alkoxy or halogen-substituted phenyl and W4 is hydrogen, especially the dye of the formula
  • a dye of the formula (3) in which R7 is hydrogen, R8 and R9 are C1-C4-alkyl, R10 is sulfo and n is the number 1, or a dye of the formula (4 ), in which B1 and B2 are independently C1-C4-alkyl or C1-C4-alkoxy, E1 is hydrogen and X is C1-C4-alkyl, or a dye of the formula (5), in which W1 is phenylsulfonyl, W2 is hydrogen, halogen or C1-C4-alkyl, W3 is phenyl optionally substituted by C1-C4-alkyl, C1-C4-alkoxy or halogen and W und is hydrogen.
  • an anthraquinone dye of the formula (1) is used together with a red-coloring dye of the formula (6) or (7) and a yellow or orange-coloring dye of the formula (9) or (11), where the meanings and preferences given above apply to the anthraquinone dye of the formula (1).
  • the present invention further provides dye mixtures which comprise at least one anthraquinone dye of the formula (1) together with at least one red-coloring dye of the formula (2) and at least one yellow or orange-coloring dye of the formulas (3), (4) and (5 ) contain.
  • the meanings and preferences given above apply to the dyes of the formulas (1), (2), (3), (4) and (5).
  • the dyes of the formulas (1), (2), (3), (4) and (5) used in the process according to the invention for trichromatic dyeing or printing are known or can be prepared analogously to known dyes.
  • the anthraquinone dyes are obtained analogously to the information in GB-A-1,438,354.
  • the dyes used in the process according to the invention for trichromatic dyeing or printing are either in the form of their free sulfonic acid or preferably as their salts.
  • suitable salts are the alkali, alkaline earth or ammonium salts or the salts of an organic amine.
  • suitable salts include the sodium, lithium, potassium or ammonium salts or the salt of mono-, di- or triethanolamine.
  • the dyes used in the process according to the invention can contain further additives such as e.g. Table salt or dextrin included.
  • the process according to the invention for trichromatic dyeing or printing can be applied to the customary dyeing or printing processes.
  • the dyeing liquors or printing pastes can contain other additives, for example wetting agents, anti-foaming agents, leveling agents or agents which influence the property of the textile material, such as e.g. Plasticizers, flame retardants or dirt, water and oil repellents, water softeners and natural or synthetic thickeners such as Alginates and cellulose ethers.
  • the process according to the invention for trichromatic dyeing or printing is also for dyeing from short liquors, such as e.g. suitable for continuous dyeing processes or discontinuous and continuous foam coloring processes.
  • the dyes used in the process according to the invention are distinguished in trichromatic dyeing or printing by uniform color build-up, good absorption behavior, good constancy of shades even in different concentrations, good fastness properties and in particular by very good combinability.
  • the process according to the invention for trichromatic dyeing or printing is suitable for dyeing or printing both natural polyamide materials such as wool, such as in particular of synthetic polyamide materials, such as polyamide 6 or polyamide 6.6, and is suitable for dyeing or printing wool and synthetic polyamide blended fabrics or yarns.
  • the textile material mentioned can be in a wide variety of processing forms, such as as fiber, yarn, woven or knitted fabric and in particular in the form of carpets.
  • parts represent parts by weight.
  • the temperatures are degrees Celsius.
  • the relationship between parts by weight and parts by volume is the same as that between grams and cubic centimeters.
  • the dyeing time at a temperature of 98 ° C is 30 to 90 minutes.
  • the dyed polyamide fiber material is then removed and rinsed and dried as usual.
  • a piece of fabric dyed in a brown shade that does not show any streakiness due to the material is obtained.
  • the anthraquinone dyes of the formulas (101), (104), (105) and (106) listed in the above examples are each used as isomer mixtures, the individual isomers differing only in the position of the sulfo group in the 6- or 7-position; the mixing ratio of the two isomers is approximately 1: 1.
  • the individual isomers can also be used as individual dyes.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
EP93810813A 1992-12-03 1993-11-24 Procédé de teinture ou d'impression par trichromie Expired - Lifetime EP0601971B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH371992 1992-12-03
CH3719/92 1992-12-03

Publications (2)

Publication Number Publication Date
EP0601971A1 true EP0601971A1 (fr) 1994-06-15
EP0601971B1 EP0601971B1 (fr) 1997-03-12

Family

ID=4262037

Family Applications (1)

Application Number Title Priority Date Filing Date
EP93810813A Expired - Lifetime EP0601971B1 (fr) 1992-12-03 1993-11-24 Procédé de teinture ou d'impression par trichromie

Country Status (5)

Country Link
US (1) US5399183A (fr)
EP (1) EP0601971B1 (fr)
JP (1) JPH06212576A (fr)
DE (1) DE59305745D1 (fr)
ES (1) ES2099409T3 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6443998B1 (en) 2000-04-14 2002-09-03 Shaw Industries, Inc. Trichromatic fiber dyeing processes and compositions thereof
DE102011079114A1 (de) * 2011-07-14 2013-01-17 Tesa Se Klebeband mit textilem Träger für die Kabelbandagierung
CN104447429B (zh) * 2014-12-25 2016-10-05 北京泛博化学股份有限公司 环保酸性可拔色黄色染料化合物、应用及合成方法
CN105753750B (zh) * 2016-02-16 2017-10-24 北京泛博清洁技术研究院有限公司 裘皮用酸性可拔白黄色染料化合物及其合成与应用方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2197940A1 (fr) * 1972-08-29 1974-03-29 Ciba Geigy Ag
EP0052578A2 (fr) * 1980-10-16 1982-05-26 Ciba-Geigy Ag Composés monoazoiques
EP0127579A1 (fr) * 1983-05-25 1984-12-05 Ciba-Geigy Ag Procédé de teinture ou d'impression en trois couleurs
US4840643A (en) * 1988-03-16 1989-06-20 Crompton & Knowles Corporation Trichromatic combination of dyes for nylon
EP0425434A2 (fr) * 1989-10-23 1991-05-02 Ciba-Geigy Ag Mélanges de colorants et leur utilisation

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0083299B2 (fr) * 1981-12-29 1990-06-13 Ciba-Geigy Ag Procédé de teinture ou d'impression en trois couleurs
DE3363254D1 (en) * 1982-04-08 1986-06-05 Ciba Geigy Ag Process for trichromatic dyeing or printing
US4579561A (en) * 1984-01-31 1986-04-01 Crompton And Knowles Corporation Process for trichromatic dyeing polyamide fibers
US4652269A (en) * 1984-11-08 1987-03-24 Ciba-Geigy Corporation Process for the continuous trichromatic dyeing of synthetic polyamide materials: including a blue anthraquinone reactive dye
EP0387201B1 (fr) * 1989-03-10 1994-02-02 Ciba-Geigy Ag Mélanges de colorants et leur utilisation
GB2236542B (en) * 1989-10-06 1992-04-15 Sandoz Ltd Dye mixtures and their use in trichromatic dyeing processes

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2197940A1 (fr) * 1972-08-29 1974-03-29 Ciba Geigy Ag
GB1438354A (en) * 1972-08-29 1976-06-03 Ciba Geigy Ag Anthraquinone dyestuffs their manufacture and their use
EP0052578A2 (fr) * 1980-10-16 1982-05-26 Ciba-Geigy Ag Composés monoazoiques
EP0127579A1 (fr) * 1983-05-25 1984-12-05 Ciba-Geigy Ag Procédé de teinture ou d'impression en trois couleurs
US4840643A (en) * 1988-03-16 1989-06-20 Crompton & Knowles Corporation Trichromatic combination of dyes for nylon
EP0425434A2 (fr) * 1989-10-23 1991-05-02 Ciba-Geigy Ag Mélanges de colorants et leur utilisation

Also Published As

Publication number Publication date
EP0601971B1 (fr) 1997-03-12
DE59305745D1 (de) 1997-04-17
ES2099409T3 (es) 1997-05-16
US5399183A (en) 1995-03-21
JPH06212576A (ja) 1994-08-02

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