EP0135198A2 - Procédé de teinture de matière fibreuse en polyamides synthétiques - Google Patents

Procédé de teinture de matière fibreuse en polyamides synthétiques Download PDF

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Publication number
EP0135198A2
EP0135198A2 EP84111089A EP84111089A EP0135198A2 EP 0135198 A2 EP0135198 A2 EP 0135198A2 EP 84111089 A EP84111089 A EP 84111089A EP 84111089 A EP84111089 A EP 84111089A EP 0135198 A2 EP0135198 A2 EP 0135198A2
Authority
EP
European Patent Office
Prior art keywords
dyes
formulas
formula
dye
hydrogen
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
EP84111089A
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German (de)
English (en)
Other versions
EP0135198B1 (fr
EP0135198A3 (en
Inventor
Heinz Salathé
Hermann Flensberg
Harry Schaetzer
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.)
Novartis AG
Original Assignee
Ciba Geigy 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 filed Critical Ciba Geigy AG
Publication of EP0135198A2 publication Critical patent/EP0135198A2/fr
Publication of EP0135198A3 publication Critical patent/EP0135198A3/de
Application granted granted Critical
Publication of EP0135198B1 publication Critical patent/EP0135198B1/fr
Expired legal-status Critical Current

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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
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/24—Polyamides; Polyurethanes
    • D06P3/241—Polyamides; Polyurethanes using acid dyes
    • 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
    • D06P1/60—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 polyethers
    • D06P1/607—Nitrogen-containing polyethers or their quaternary derivatives
    • D06P1/6076—Nitrogen-containing polyethers or their quaternary derivatives addition products of amines and alkylene oxides or oxiranes
    • 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
    • Y10S534/00—Organic compounds -- part of the class 532-570 series
    • Y10S534/01—Mixtures of azo compounds
    • 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 new process for dyeing synthetic polyamide materials with anionic dyes of different dye classes in light to dark shades from an aqueous liquor, dyeing at a constant pH of 5 to 7 regardless of the depth of color of the dyeing and regardless of the dye class used is, the dye bath is practically completely pulled out and the dyeing shows good overall fastness properties, in particular good wet fastness properties and good light fastness, and the material dyed by the new process.
  • a disadvantage of the dyeing processes used hitherto for synthetic polyamides is that dyeing must be carried out at different pH values both in order to achieve light and dark shades and when using dyes from different dye classes.
  • the pH value of the dye bath is of crucial importance with regard to the reproducibility of the dyeings.
  • auxiliaries matched to the respective dye class are used for leveling and to cover material-related streakiness; i.e. the auxiliaries used in the usual dyeing processes cannot be applied equally well to all dye classes. Especially when combining dyes
  • the present invention thus relates to a process for dyeing fiber material from synthetic polyamides with dyes or dye mixtures in the presence of an auxiliary mixture, which is characterized in that an aqueous liquor is used for dyeing these materials, which contains at least one anionic dye, which is defined under the Dyeing conditions at a depth of 1/1 standard has a degree of exhaustion of at least 95%, and an auxiliary mixture containing an anionic compound, a quaternary compound and a nonionic.
  • the liquor contains an alkali salt and an organic acid, and the coloring at a pH of 5 to 7, preferably 5.5 to 6, and at a temperature of 95 to 130 ° C completed.
  • An auxiliary mixture is preferably an auxiliary mixture, which is an anionic compound of the formula wherein R is an alkyl or alkenyl radical having 12 to 22 carbon atoms, H is hydrogen, alkali metal or ammonium and m and n are integers, the sum of m and n being 2 to 14, a quaternary compound of the formula wherein R 'independently of R has the meaning given for R, A is an anion, Q is an optionally substituted alkyl radical and p and q are integers, the sum of p and q being 20 to 50, and a nonionic compound of the formula where R "independently of R has the meaning given for R and x and y are integers, the sum of x and y being 80 to 140.
  • the anionic dyes that can be used can belong to the most diverse classes of dyes and optionally contain one or more sulfonic acid groups and optionally one or more fiber-reactive groups.
  • these are triphenylmethane dyes with at least two sulfonic acid groups, heavy metal-free monoazo and disazo dyes each with one or more sulfonic acid groups and optionally one or more fiber-reactive groups and heavy metal-containing monoazo, disazo, azomethine, especially those containing copper, chromium, nickel or cobalt - And formazan dyes, in particular metallized dyes, two to one metal atom Molecules contain azo dye or a molecule of azo dye and a molecule of azomethine dye, especially those that contain mono- and / or disazo dyes and / or azomethine dyes as ligands and a chromium or cobalt ion as the central metal ion, as well as anthraquinone dyes
  • the amounts in which the dyes are used in the dyebaths can vary within wide limits depending on the desired depth of color. In general, amounts of 0.001 to 6 percent by weight, based on the material to be dyed, of one or more dyes have proven to be advantageous.
  • 1/1 standard depth is understood to mean the color depth 1/1 designated in accordance with DIN (German Industry Standard) 54000.
  • a degree of exhaustion of at least 95% means that less than 5% of the amount of dye used in the process according to the invention remains in the bath after dyeing.
  • Trichromatic is understood to mean 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.
  • Anionic dyes are preferably used in the process according to the invention, which have a degree of exhaustion of at least 97% under the defined dyeing conditions at 1/1 standard depth.
  • Reactive residues particularly suitable for polyamide are: chloroacetyl, bromoacetyl, ⁇ , ⁇ -dichloro- or a, p-dibromopropionyl, a-chloro- or ⁇ -bromoacryloyl, 2,4-difluoro-5-chloropyrimidyl-6, 2,4,6 -Trifluoropyrimidyl-5, 2,4-dichloro-5-methylsulfonylpyrimidinyl-6, 2-fluoro-4-methyl-5-chlorpyrimidyl-6, 2,4-difluoro-5-methyl-sulfonylpyrimidyl - 6, 2,4-Difluorotriazinyl -6, and fluorotriazinyl residues of the formula wherein R 26 represents an optionally substituted amino group or an optionally etherified oxy or thio group, such as the NH 2 group, an amino group mono- or disubstituted with
  • the benzene rings dashed in formulas (11) and (15) mean a benzene ring which may be condensed onto the phenol residue written out, so that the dyes optionally contain a phenol or naphthol residue.
  • the dyes containing sulfo groups used in the process according to the invention are present either in the form of their free sulfonic acid or preferably as their salts.
  • suitable salts are the alkali metal, alkaline earth metal or ammonium salts or the salts of an organic amine.
  • suitable salts include the sodium, lithium, potassium or ammonium salts or the salt of triethanolamine.
  • M ⁇ in the above formulas (35) to (39) is an alkali, alkaline earth or ammonium ion, such as the sodium, potassium, lithium or ammonium ion.
  • dye mixtures are used in the process according to the invention, these can be prepared by mixing the individual dyes. This mixing process takes place, for example, in suitable mills, e.g. Ball and pin mills, as well as in kneaders or mixers.
  • the dye mixtures can be prepared by spray drying the aqueous dye mixtures.
  • Preferred in the process according to the invention are the dyes of the formulas (62) to (65) and the dye mixtures of the dyes of the formulas (23) + (24) + ' (30) + (39), (25) + (42), ( 26) + (26a) + (27), (31) + (38), (40) + (44), (41) + (54), (32) + (37) + (56), (35) + (39) + (53) + (57), (36) + (51) + (53), (43) + (45) + (46) + (47) + (49) and (51) + ( 55).
  • the individual dyes and the dye mixtures are characterized by their excellent combinability, which means that almost all of the nuances for synthetic polyamide material can be covered.
  • the radicals R, R 'and R "in the formulas (1), (2) and (3) are, independently of one another, alkyl or alkenyl radicals having 12 to 22, preferably 16 to 22, carbon atoms. Examples include: the n -Dodecyl, myristyl, n-hexadecyl, n-heptadecyl, n-octadecyl, arachidyl, behenyl, dodecenyl, hexadecenyl, oleyl and octadecenyl radical.
  • the radical M in formula (1) is hydrogen, alkali metal such as e.g. Sodium or potassium and especially ammonium.
  • the radical Q and the anion A ⁇ in formula (2) are derived from quaternizing agents , where Q is an optionally substituted alkyl radical.
  • quaternizing agents are, for example, chloroacetamide, ethyl bromide, ethylene chlorohydrin, ethylene bromohydrin, epichlorohydrin, epibromohydrin and in particular dimethyl sulfate.
  • An auxiliary mixture containing 5 to 70 parts of the compound of the formula (1), 15 to 60 parts of the compound of the formula (2) and 5 to 60 parts of the compound of the formula (3), based on 100 parts, is preferably used in the process according to the invention of the auxiliary mixture.
  • an auxiliary mixture which, in addition to the compounds of the formulas (1), (2) and (3), also contains an adduct of 60 to 100 parts of ethylene oxide with part of a C 15-20 alkenyl alcohol.
  • a C 15-20 alkenyl alcohol are: hexadecenyl, oleyl and octadecenyl alcohol. 5 to 10 parts, in particular 7 to 9 parts of the adduct, based on 100 parts of the auxiliary mixture, are preferably used.
  • the amounts in which the auxiliary mixture consisting of the compounds of the formulas (1), (2) and (3) and, if appropriate, the adduct of ethylene oxide with a C 15-20 alkenyl alcohol described above are added to the dyebath are between 0 , 5 and 2 percent by weight based on the fiber material to be dyed. Preferably, 1 percent by weight of the auxiliary mixture based on the fiber material is used.
  • the dyebaths contain organic acids, suitably lower, aliphatic carboxylic acids, e.g. especially acetic acid.
  • the acids primarily serve to adjust the pH of the liquors used according to the invention.
  • the dyeing liquor also contains alkali salts such as e.g. Sodium acetate. Preferably 2 g / 1 sodium acetate are used.
  • the dyebaths can also contain other customary additives, such as Contain wetting and defoaming agents, deaerators and penetration accelerators.
  • the liquor ratio can be selected within a wide range, from 1: 5 to 1:40, preferably 1: 8 to 1:25.
  • Dyeing is carried out from an aqueous liquor using the exhaust process, e.g. at temperatures between 95 and 130 ° C, preferably at cooking temperature.
  • the dyeing time is usually 10 to 50 minutes at the dyeing end temperature.
  • the customary dyeing apparatus and machines for example for flake, sliver, strand yarn, bobbins, piece goods and carpets, can be used.
  • the auxiliary mixture is expediently mixed into the aqueous dye liquor and applied simultaneously with the dye.
  • the fiber material is preferably added to a liquor which contains 2 g / l of sodium acetate and a sufficient amount of acetic acid and the auxiliary mixture to adjust the pH from 5.5 to 6 and which has a temperature of 30 to 70 ° C.
  • the dye or a dye mixture is then added and the temperature of the dyebath at a heating rate of 0.75 to 3 ° C per minute, optionally with a temperature stop during the Heating, increased to color in the specified temperature range of 95 to 130 ° C, preferably 10 to 50 minutes.
  • the bath is cooled and the colored material rinsed and dried as usual.
  • All known synthetic polyamides can be considered as fiber material made of synthetic polyamides which can be dyed according to the invention.
  • the fiber material can be in a wide variety of forms, e.g. as loose material, sliver, yarn and piece goods or as carpet.
  • the method according to the invention has the following advantages over the known methods for fiber material made of synthetic polyamides in addition to the already mentioned.
  • the material dyed in this way under uniform dyeing conditions is distinguished by an excellent reproducibility of the desired shade.
  • the dyeings obtained are also notable for good overall fastness properties, in particular good light and wet fastness properties, and they are colored regardless of the color shade and even regardless of the selected mixture of different dye types. Another important advantage is that the dyes are almost completely absorbed. When dyeing is complete, the dye baths are almost completely drawn out.
  • the compounds of formula (1) can be prepared by adding 2 to 14 mol of ethylene oxide to aliphatic amines which have an alkyl or alkenyl radical having 12 to 22 carbon atoms, and adding the adduct into the acidic ester and, if appropriate, the acidic ester obtained the alkali or ammonium salts are transferred.
  • the Compounds of the formula (2) are prepared by, for example, adding 20 to 50 mol of ethylene oxide to aliphatic amines which have an alkyl or alkenyl radical having 12 to 22 carbon atoms, and the adduct with one of the quaternizing agents mentioned above to give the compound of the formula ( 2) implements.
  • the compounds of formula (3) are prepared by adding 80 to 140 moles of ethylene oxide to a compound of formula wherein R "has the meaning given under formula (3).
  • the amines which are required as starting materials for the preparation of the compounds of the formulas (1) and (2) can have saturated or unsaturated, branched or unbranched hydrocarbon radicals having 12 to 22, preferably 16 to 22, carbon atoms.
  • the amines can be chemically uniform or in the form of mixtures.
  • Dodecylamine, hexadecylamine, octadecylamine, arachidylamine, behenylamine and octadecenylamine may be mentioned as amines.
  • Tallow fatty amine is preferred. This is a mixture of 30% hexadecylamine, 25% octadecylamine and 452 octadecenylamine.
  • Both the ethylene oxide addition and the esterification can be carried out according to methods known per se.
  • sulfuric acid or its functional derivatives such as e.g. Chlorosulfonic acid and especially sulfamic acid are used.
  • the esterification is generally carried out by simply mixing the reactants with heating, advantageously to a temperature between 50 and 100 ° C.
  • the free acids can then be converted into the alkali metal or ammonium salts by using bases such as e.g. Ammonia, sodium or potassium hydroxide can be added.
  • the following examples serve to illustrate the invention.
  • the parts are parts by weight and the percentages are percentages by weight.
  • the temperatures are given in degrees Celsius.
  • the relationship between parts by weight and parts by volume is the same as that between grams and cubic centimeters.
  • Example 10 700 g of polyamide 6 flake are wetted in 11 l of water at 40 ° C. in a circulation dyeing machine. Then 0.12 ml / 1 80% acetic acid, 2 g / 1 sodium acetate and 7 g of the auxiliary medium mixture A 1 added. After 10 minutes, 8.4 g of the 1: 2 mixed complexes become the 1: 1 chromium complex of the dye of the formula implemented with the metallizable dyes of the formulas 8.4 g of the dye of the formula to the corresponding 1: 2 mixed complexes 1 g of the dye of the formula 1.6 g of the dye of the formula and 0.35 g of the dye of the formula admitted.
  • the dyeing liquor is heated to 120 ° C. within 45 min and dyed at this temperature for 10 min.
  • the dyebath is then cooled and the polyamide 6 flake is rinsed and dried. A black coloring of the polyamide 6 flake is obtained.
  • the pH of the dyebath is 5.7 at the beginning and 5.9 at the end.
  • the degree of exhaustion is 96%.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
EP84111089A 1983-09-19 1984-09-17 Procédé de teinture de matière fibreuse en polyamides synthétiques Expired EP0135198B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH5080/83 1983-09-19
CH508083 1983-09-19

Publications (3)

Publication Number Publication Date
EP0135198A2 true EP0135198A2 (fr) 1985-03-27
EP0135198A3 EP0135198A3 (en) 1985-06-12
EP0135198B1 EP0135198B1 (fr) 1989-05-10

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EP84111089A Expired EP0135198B1 (fr) 1983-09-19 1984-09-17 Procédé de teinture de matière fibreuse en polyamides synthétiques

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US (1) US4563192A (fr)
EP (1) EP0135198B1 (fr)
JP (1) JPS6088186A (fr)
DE (1) DE3478129D1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0181293A3 (en) * 1984-11-08 1987-10-14 Ciba-Geigy Ag Process for dyeing synthetic polyamide materials with anthrachinone reactive dyes
EP0181292A3 (en) * 1984-11-08 1987-10-14 Ciba-Geigy Ag Process for the continuous trichromatic dyeing of synthetic polyamide materials
EP0593392A1 (fr) * 1992-09-30 1994-04-20 Ciba-Geigy Ag Procédé de teinture de fibres polyamides naturelles et synthétiques avec des mélanges de colorants

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0203890B1 (fr) * 1985-05-24 1990-01-03 Ciba-Geigy Ag Procédé de teinture de matières en polyamides naturels avec des mélanges de colorants
DE58907709D1 (de) * 1988-06-29 1994-06-30 Ciba Geigy Faserreaktive Formazanfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung.
JPH0219577A (ja) * 1988-07-04 1990-01-23 Nippon Saafuakutanto Kogyo Kk 反応染料用均染剤組成物
EP0360735A1 (fr) * 1988-08-26 1990-03-28 Ciba-Geigy Ag Procédé pour la teinture ou l'impression par trichromie
EP0410931B1 (fr) * 1989-07-24 1994-06-01 Ciba-Geigy Ag Colorants formazane réactifs avec des fibres, leurs procédés de préparation et leur utilisation
EP0555182B1 (fr) * 1992-02-06 1998-03-04 Ciba SC Holding AG Procédé de teinture de fibres polyamides naturelles ou synthétiques
DE59309441D1 (de) * 1992-02-28 1999-04-22 Ciba Geigy Ag Verfahren zum Färben von Leder mit Farbstoffmischungen
US5427589A (en) * 1993-03-03 1995-06-27 Springs Industries, Inc. Method for dyeing fibrous materials
EP0625550B1 (fr) * 1993-05-18 1999-09-01 Ciba SC Holding AG Mélanges de colorants, colorants formazaniques complexes 1:2 de cobalt et leurs utilisation
US6551364B2 (en) 1993-05-18 2003-04-22 Ciba Specialty Chemicals Corporation Dye mixtures, 1:2 cobalt complex formazan dyes and their use
US5437690A (en) * 1994-05-25 1995-08-01 Springs Industries, Inc. Method for dyeing fibrous materials and dye assistant relating to the same
DE10028224A1 (de) * 2000-06-07 2002-01-03 Bayer Ag Mischungen von Schwefelsäureestern
JP2015063631A (ja) * 2013-09-26 2015-04-09 日本化薬株式会社 アゾ化合物
CN103694740B (zh) * 2014-01-13 2015-07-01 上海雅运纺织化工股份有限公司 藏青色酸性染料组合物及其染色应用
CN107043553B (zh) * 2016-12-14 2019-04-23 恒升化工有限公司 一种酸性染料的制备方法
CN117004248A (zh) * 2023-08-08 2023-11-07 约克夏(浙江)染化有限公司 黑色酸性染料组合物、黑色酸性染料及其制备方法和用途

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH4381A (fr) * 1891-12-16 1892-04-30 Joseph Magnat Un vélocipède perfectionné
CH6418A (de) * 1893-03-15 1893-08-15 Franz Weyland Vorrichtung zur einseitigen Färbung von Papier
CH10130A (fr) * 1895-03-01 1895-10-15 Auguste Bachelay Nouvelle enveloppe de sûreté pour assurer le secret de la correspondance et empêcher la soustraction des valeurs
CH391664A4 (de) * 1964-03-26 1966-02-28 Geigy Ag J R Verfahren zum Färben von synthetischen Polyamidfasern mit neutral bis schwach sauer ziehenden anionischen Wollfarbstoffen
CH465554A (de) * 1966-07-12 1969-01-15 Ciba Geigy Verfahren zum Färben von Textilmaterial aus synthetischem Polyamid mit wasserlöslichen 1:2-Chrom- oder Kobaltkomplexfarbstoffen
CH553286A (fr) * 1969-03-24 1974-08-30
US4444563A (en) * 1981-09-07 1984-04-24 Ciba-Geigy Corporation Dyeing assistant and use thereof in dyeing or printing synthetic polyamide fibre materials
ATE20099T1 (de) * 1981-12-29 1986-06-15 Ciba Geigy Ag Verfahren zum trichromie-faerben oder -bedrucken.
DE3363011D1 (en) * 1982-03-12 1986-05-22 Ciba Geigy Ag Process for dyeing fibrous material from natural polyamides
ATE19533T1 (de) * 1982-04-08 1986-05-15 Ciba Geigy Ag Verfahren zum trichromie-faerben oder -bedrucken.

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0181293A3 (en) * 1984-11-08 1987-10-14 Ciba-Geigy Ag Process for dyeing synthetic polyamide materials with anthrachinone reactive dyes
EP0181292A3 (en) * 1984-11-08 1987-10-14 Ciba-Geigy Ag Process for the continuous trichromatic dyeing of synthetic polyamide materials
EP0593392A1 (fr) * 1992-09-30 1994-04-20 Ciba-Geigy Ag Procédé de teinture de fibres polyamides naturelles et synthétiques avec des mélanges de colorants
US5356445A (en) * 1992-09-30 1994-10-18 Ciba-Geigy Corporation Process for dyeing natural or synthetic polyamide fibre material with dye mixtures

Also Published As

Publication number Publication date
DE3478129D1 (en) 1989-06-15
JPS6088186A (ja) 1985-05-17
EP0135198B1 (fr) 1989-05-10
US4563192A (en) 1986-01-07
EP0135198A3 (en) 1985-06-12

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