EP0089004B1 - Verfahren zum Färben von Fasermaterial aus natürlichen Polyamiden - Google Patents

Verfahren zum Färben von Fasermaterial aus natürlichen Polyamiden Download PDF

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Publication number
EP0089004B1
EP0089004B1 EP83102325A EP83102325A EP0089004B1 EP 0089004 B1 EP0089004 B1 EP 0089004B1 EP 83102325 A EP83102325 A EP 83102325A EP 83102325 A EP83102325 A EP 83102325A EP 0089004 B1 EP0089004 B1 EP 0089004B1
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EP
European Patent Office
Prior art keywords
dyes
formula
formulae
dyeing
process according
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.)
Expired
Application number
EP83102325A
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German (de)
English (en)
French (fr)
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EP0089004A1 (de
Inventor
Heinz Salathé
Hermann Flensberg
Harry Schaetzer
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Novartis AG
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Ciba Geigy AG
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Publication of EP0089004A1 publication Critical patent/EP0089004A1/de
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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
    • 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
    • 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
    • D06P3/06—Material containing basic nitrogen containing amide groups using acid 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
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/917—Wool or silk

Definitions

  • the present invention relates to a uniform new method for fiber and surface level dyeing of natural polyamide materials with anionic wool dyes of different dye classes in light to dark shades from an aqueous liquor, regardless of the depth of color of the dyeing and regardless of the dye class used for natural polyamide material with a gentle pH -Value is dyed, the dyebath is virtually completely pulled out and the dyeing shows good overall fastness properties, in particular good wet fastness properties and good light fastness.
  • a disadvantage of the dyeing processes for natural polyamides which have been customary hitherto is that dyeing at different pH values is necessary both in order to achieve light and dark shades and when using dyes from different dye classes. It is known from the literature, for example, that with well-leveling acid dyes at a pH of 2 to 3.5, with non-fading acid dyes at a pH of 4 to 5, with highly milled acid dyes at a pH of 6 to 7, with 1: 2 metal complex dyes without sulfo groups at a pH of 5 to 7, with 1: 2 metal complex dyes with sulfo groups at a pH of 4 to 7, with 1: 1 metal complex dyes at a pH of 1.9 up to 2.8 and with reactive dyes at a pH of 4.5 to 7.
  • the pH value of the dyebath is of crucial importance when dyeing natural polyamide materials, especially when dyeing wool, since wool is particularly attacked both in the strongly acidic and in the alkaline pH range.
  • auxiliaries which are matched to the respective dye class are used to equalize the affinity differences of the wool (dichroism), since the dichroism depends on the hydrophilicity of the dyes used; d. H.
  • the auxiliaries used in the usual dyeing processes cannot be applied to all dye classes with equally good results. Irregularities in color and shade occur in particular when hydrophilic dyes are combined with more hydrophobic dyes. In many cases, the surface-level coloring of natural polyamide materials is also unsatisfactory.
  • FR-A-2 444 746, CH-B-363 006, CH-A-429 763, CH-B-465 553 and CH-A-17413 are further processes for dyeing wool and from GB-A-
  • a further process for dyeing synthetic polyamides is known from 1,160,343.
  • the present invention thus relates to a process for fiber and flat level dyeing of fiber material made of natural polyamides or wool / polyamide, wool / polyester, wool / cellulose or wool / polyacrylonitrile fiber mixtures with dyes or dye mixtures in the presence of an auxiliary mixture, which is characterized in that for coloring these Mate ialien r using an aqueous liquor containing at least one anionic wool dye which under the defined dyeing conditions at the color depth of 1/1 according to DIN 54000 having a degree of exhaustion of at least 95%, and an assistant mixture consisting of an anionic compound of the formula wherein R is an alkyl or alkenyl radical having 12 to 22 carbon atoms, M 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
  • the anionic wool dyes that can be used can belong to the most varied classes of dyes and can optionally contain one or more sulfonic acid groups and optionally one or more fiber-reactive groups.
  • it is 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 containing copper, chromium, nickel or cobalt and formazan dyes, in particular metallized dyes, which contain two molecules of azo dye or one molecule of azo dye and one molecule of azomethine dye bonded to a metal atom, especially those containing mono- and / or disazo dyes and / or azomethine dyes as ligands and a chromium as the central metal ion.
  • Fiber-reactive groups are understood to be those groups which form a covalent bond with the natural polyamide material to be colored.
  • Dyes containing one or more fiber-reactive groups are in the invention. method preferably used in combination with non-fiber-reactive 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 10 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 means the additive farm mix 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 wool 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.
  • Anthraquinone dyes of the formulas wherein T is hydrogen or C 1-4 alkyl, e 0 or 1, and R 9 has the meaning given under formula (6), R 22 is independently hydrogen or C 1-4 alkyl and R 23 is hydrogen or sulfo ; wherein the substituents R 24 are, independently of one another, cyclohexyl and the diphenyl ether radical, which can be substituted by sulfo and the radical ⁇ CH 2 NH ⁇ Rg, where R 9 has the meaning given under formula (6); and wherein R 9 has the meanings given under formula (6) and R 22 has the meanings given under formula (20) and R 25 is C 4-8 alkyl.
  • Reactive residues particularly suitable for wool are: chloroacetyl, bromoacetyl, a, ß-dichloro- or a, ß-dibromopropionyl, a-chloro- or a-bromoacryloyl, 2,4-difluoro-5-chloropyrimidyl-6, 2,4,6 -Trifluoropyrimidyl-5, 2,4-dichloro-5-methylsulfonylpyrimidinyl-6, 2-fluoro-4-methyl-5-chloropyrimidyl-6., 2,4-difluoro-5-methylsulfonylpyrimidyl-6, 2,4-difluorotriazinyl- 6, and fluorotriazinyl radicals of the formula wherein R 26 is an optionally substituted amino group or an optionally etherified oxy- or thio group, such as.
  • the 1: 2 chromium complexes of the azo dyes of the formulas the symmetrical 1: 2 chromium complexes of the azo dyes of the formulas the symmetrical 1: 2 cobalt complexes of the azo dyes of the formulas the 1: 2 chromium complexes of the mixture of azo dyes of the formulas
  • 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 formulas (35) to (39) above is an alkali, alkaline earth or ammonium ion such as 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. B. ball and pin mills, as well as in kneaders or mixers.
  • the dye mixtures can be prepared by spray drying the aqueous dye mixtures.
  • the dyes of the formulas (62) to (65) and the dye mixtures of the dyes of the formulas (24) + (39, (25) + (42), (26) + (27), (31) are preferred in the process according to the invention. + (38), (40) + (44), (41) + (54), (32) + (37) + (56), (35) + (39) + (53) + (57), ( 36) + (51) + (53), (43) + (45) + (46) + (47) + (48) + ( 49 ) and (51) + (55)
  • the individual dyes and the dye mixtures stand out due to its excellent combinability, which covers almost all nuances for natural polyamide material.
  • 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, for. B. 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 e.g. B. chloroacetamide, ethyl bromide, ethylene chlorohydrin, ethylene bromohydrin, epichlorohydrin, epibromohydrin and especially dimethyl sulfate.
  • An auxiliary mixture consisting of 5 to 70 parts by weight of the compound of the formula (1), 15 to 60 parts by weight of the compound of the formula (2) and 5 to 60 parts by weight of the compound of the formula (3), based on 100, is preferably used in the process according to the invention Parts by weight of that 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 mol of ethylene oxide with one mol of a C, 5-20 -alkylenyl alcohol.
  • Examples of a C 15 -zo alkenyl alcohol are: hexadecenyl, oleyl and octadecenyl alcohol.
  • auxiliary mixture consisting of the compounds of the formulas (1), (2) and (3) and, if appropriate, the adduct of ethylene oxide with a C, 5 described above.
  • 20 -Alkenyl alcohol are added to the dyebath, preferably between 0.5 and 2 percent by weight based on the fiber material to be dyed.
  • 1 percent by weight of the auxiliary mixture based on the fiber material is used.
  • the dyebaths can contain mineral acids, such as sulfuric acid or phosphoric acid, organic acids, expediently lower, aliphatic carboxylic acids, such as formic, acetic or oxalic acid.
  • mineral acids such as sulfuric acid or phosphoric acid
  • organic acids expediently lower, aliphatic carboxylic acids, such as formic, acetic or oxalic acid.
  • the acids primarily serve to adjust the pH of the liquors used according to the invention.
  • the dye liquor salts especially ammonium or alkali salts such as. B. ammonium sulfate, ammonium or sodium acetate or preferably sodium sulfate. Preferably 0.1 to 10 weight percent ammonium or alkali sulfate based on the fiber material is used.
  • the dye baths can also contain other customary additives, such as, for. B. contain wool protection, wetting and defoaming agents.
  • the liquor ratio can be selected within a wide range, from 1: 5 to 1:40, preferably 1: 8 to 1:25.
  • the dyeing is carried out from an aqueous liquor by the exhaust process, for. B. at temperatures between 95 and 105 ° C, preferably between 98 and 103 ° C.
  • the dyeing time is usually 10 to 50 minutes.
  • the usual dyeing apparatus and machines can be used, for example for flake, sliver, sliver, bobbin, piece goods and carpets.
  • 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 acid and the auxiliary mixture and has a temperature of 30 to 70 ° C.
  • the dye or a dye mixture is then added and the temperature of the dyebath is increased at a heating rate of 0.75 to 3 ° C. per minute, optionally with a temperature stop during heating, to preferably 10 to in the specified temperature range from 95 to 105 ° C. 50 minutes to dye.
  • the bath is cooled and the colored material rinsed and dried as usual.
  • fiber material made of natural polyamides which can be dyed according to the invention, above all wool, but also mixtures of wool / polyamide, wool / polyester, wool / cellulose or wool / polyacrylonitrile and silk should be mentioned.
  • the fiber material can be in a wide variety of packaging, such as. B. as a loose material crest, yarn and piece goods or as a carpet.
  • the method according to the invention has the following advantages over the known methods for fiber material made from natural polyamides in addition to the already mentioned.
  • the material so dyed under uniform dyeing conditions excels in further processing such as. B. from spinning by similar behavior.
  • the dyeings obtained are also notable for good overall fastness properties, in particular good light and wet fastness properties, and they are dyed regardless of the color shade and even regardless of the mixture selected on different types of dyes, regardless of fiber and area.
  • Another important advantage is that the dyes are almost completely absorbed. After dyeing is complete, the dye baths are completely or almost completely drawn out, which enables repeated use of the heated aqueous liquor solution, which requires less energy.
  • the invention further relates to the dyeing auxiliary mixture, which is an anionic compound of the formula wherein R is an alkyl or alkenyl radical having 12 to 22 carbon atoms, M 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.
  • R is an alkyl or alkenyl radical having 12 to 22 carbon atoms
  • M is hydrogen, alkali metal or ammonium
  • m and n are integers, the sum of m and n being 2 to 14
  • the dyeing aid mixture preferably contains 5 to 70 parts by weight of the compound of the formula (1), 15 to 60 parts by weight of the compound of the formula (2) and 5 to 60 parts by weight of the compound of the formula (3), based on 100 parts by weight of the dyeing aid mixture.
  • R, R 'and R have the meanings given above.
  • R, R' and R" in the formulas (1), (2) and ( 3) independently of one another an alkyl or alkenyl radical having 16 to 22 carbon atoms.
  • the dyeing auxiliary mixture preferably also contains an adduct of 60 to 100 mol of ethylene oxide with a C, 5 . 20 alkenyl alcohol.
  • 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 formula (2) are prepared by e.g. B. 20 to 50 moles of ethylene oxide to aliphatic amines which have an alkyl or alkenyl radical having 12 to 22 carbon atoms, and the adduct is reacted with one of the quaternizing agents mentioned above to give the compound of the formula (2).
  • 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.
  • amine mixtures such as those used in the transfer of natural fats or oils such as z. B. tallow fat, soy, or coconut oil in the corresponding amines.
  • Dodecylamine, hexadecylamine, octadecylamine, arachidylamine, behenylamine and octadecenylamine may be mentioned as amines.
  • Talgefettamine is preferred. This is a mixture of 30% hexadecylamine, 25% octadecylamine and 45% 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. B. chlorosulfonic acid and especially sulfamic acid.
  • 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. B. 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.
  • Cross-wound bobbins are loaded with 140 kg of wool yarn in a cross-wound dyeing machine and wetted in 840 l of water at 60 ° C. Then you put 840 g of sodium acetate, 4,200 g of 60% acetic acid, 7,200 g of Glauber's salt. and 2800 g of the assistant mixture to a 3. After 20 minutes, 850 g of the dye of the formula and 153 g of the dye of the formula added. The temperature is raised to 104 ° C. within 40 minutes and dyeing is carried out at this temperature for 20 minutes. The packages are then rinsed, dewatered and dried. A blue dyeing of the wool yarn with good fiber and surface levelness is obtained. The pH is between 4.8 and 5.0 during dyeing. The degree of exhaustion is 95%.

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  • Textile Engineering (AREA)
  • Coloring (AREA)
EP83102325A 1982-03-12 1983-03-09 Verfahren zum Färben von Fasermaterial aus natürlichen Polyamiden Expired EP0089004B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH155682 1982-03-12
CH1556/82 1982-03-12

Publications (2)

Publication Number Publication Date
EP0089004A1 EP0089004A1 (de) 1983-09-21
EP0089004B1 true EP0089004B1 (de) 1986-04-16

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EP83102325A Expired EP0089004B1 (de) 1982-03-12 1983-03-09 Verfahren zum Färben von Fasermaterial aus natürlichen Polyamiden

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US (1) US4444564A (pt)
EP (1) EP0089004B1 (pt)
JP (2) JPS58191285A (pt)
AU (1) AU551980B2 (pt)
CA (1) CA1199453A (pt)
DE (1) DE3363011D1 (pt)
NZ (1) NZ203541A (pt)
ZA (1) ZA831694B (pt)

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FR2552791B1 (fr) * 1983-09-29 1986-12-05 Sandoz Sa Procede de teinture de substrats textiles comprenant de la laine
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DE3564830D1 (en) * 1984-05-30 1988-10-13 Ciba Geigy Ag Process for dyeing natural or synthetic polyamide fibrous material with 1:1 metallic complex dyes
DE3578870D1 (de) * 1984-11-08 1990-08-30 Ciba Geigy Ag Verfahren zum kontinuierlichen trichromie-faerben von synthetischen polyamidmaterialien.
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CH668981A5 (de) * 1985-06-27 1989-02-15 Sandoz Ag Badstabile zubereitungen von wasserloeslichen metallkomplexfarbstoffen.
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DE3539475A1 (de) * 1985-11-07 1987-05-14 Hoechst Ag Verfahren zum faerben von wollstueckware
DE3544795A1 (de) * 1985-12-18 1987-06-19 Hoechst Ag Verfahren zum faerben von wolle mit reaktivfarbstoffen
EP0263063A1 (de) * 1986-09-10 1988-04-06 Ciba-Geigy Ag Feste Formulierung von anionischen Wollfarbstoffen
US4818248A (en) * 1986-10-10 1989-04-04 Ciba-Geigy Corporation Process for dyeing natural or synthetic polyamide fibre materials with 1:1 metal complex dyes in presence of alkali metal fluordsilicate or amindnlum silicate
FR2611737B1 (fr) * 1987-03-04 1993-07-23 Sandoz Sa Melanges de colorants anioniques pour la teinture de la laine
FR2611763B1 (fr) * 1987-03-04 1990-03-09 Sandoz Sa Procede de teinture de polyamides naturels et/ou synthetiques avec des colorants anioniques
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ES2053804T3 (es) * 1987-09-21 1994-08-01 Ciba Geigy Ag Procedimiento para teñir o estampar materiales de fibras poliamidicas naturales o sinteticas con colorantes reactivos.
JPH01168979A (ja) * 1987-11-13 1989-07-04 Sandoz Ag 皮革の染色法
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 (de) * 1988-08-26 1990-03-28 Ciba-Geigy Ag Verfahren zum Trichromie-Färben oder -Bedrucken
EP0378048A1 (de) * 1988-12-23 1990-07-18 Ciba-Geigy Ag Styroloxid-Anlagerungsprodukte
DE59005892D1 (de) * 1989-07-24 1994-07-07 Ciba Geigy Faserreaktive Formazanfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung.
EP0419413A1 (de) * 1989-09-22 1991-03-27 Ciba-Geigy Ag Verfahren zum Färben oder Bedrucken von Mischfasern aus cellulosehaltigen Fasermaterialien und Seide
ES2067902T5 (es) * 1990-02-14 1998-04-16 Ciba Geigy Ag Procedimiento para la tintura de la lana con colorantes reactivos.
DE59108604D1 (de) * 1990-08-28 1997-04-17 Ciba Geigy Verfahren zum Färben von Wolle und deren Mischungen mit anderen Fasern mit Reaktivfarbstoffen
JPH04209875A (ja) * 1990-12-05 1992-07-31 Toyobo Co Ltd 染色された交編編地とその製法
EP0548013A1 (de) * 1991-12-16 1993-06-23 Ciba-Geigy Ag Verfahren zum Färben von Wolle mit Hilfe einer Niedertemperaturplasma- oder Corona-Vorbehandlung
ES2115042T3 (es) * 1992-02-06 1998-06-16 Ciba Geigy Ag Procedimiento para teñir fibras naturales o sinteticas de poliamida.
EP0593392B1 (de) * 1992-09-30 1996-07-24 Ciba-Geigy Ag Verfahren zum Färben von natürlichen und synthetischen Polyamidfasermaterialien mit Farbstoffmischungen
GB0212691D0 (en) * 2002-06-05 2002-07-10 Clariant Int Ltd Composition for dyeing polyester textile materials
CN102995465B (zh) * 2012-11-08 2015-01-07 西安工程大学 拉细羊毛-普通羊毛混合毛条染色助剂wpn及染色方法

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JPS58191285A (ja) 1983-11-08
US4444564A (en) 1984-04-24
NZ203541A (en) 1986-06-11
JPS6327474B2 (pt) 1988-06-03
AU551980B2 (en) 1986-05-15
CA1199453A (en) 1986-01-21
ZA831694B (en) 1985-03-27
JPS61245385A (ja) 1986-10-31
EP0089004A1 (de) 1983-09-21
DE3363011D1 (en) 1986-05-22
AU1239683A (en) 1983-09-15
JPS6111348B2 (pt) 1986-04-02

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