EP0442844B1 - Procédé de teinture de la laine avec des colorants réactifs - Google Patents

Procédé de teinture de la laine avec des colorants réactifs Download PDF

Info

Publication number
EP0442844B1
EP0442844B1 EP91810078A EP91810078A EP0442844B1 EP 0442844 B1 EP0442844 B1 EP 0442844B1 EP 91810078 A EP91810078 A EP 91810078A EP 91810078 A EP91810078 A EP 91810078A EP 0442844 B1 EP0442844 B1 EP 0442844B1
Authority
EP
European Patent Office
Prior art keywords
component
hydrogen
formula
compound
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 - Lifetime
Application number
EP91810078A
Other languages
German (de)
English (en)
Other versions
EP0442844B2 (fr
EP0442844A1 (fr
Inventor
Klaus Dr. Hannemann
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=4187901&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP0442844(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Ciba Geigy AG, Ciba Spezialitaetenchemie Holding AG filed Critical Ciba Geigy AG
Publication of EP0442844A1 publication Critical patent/EP0442844A1/fr
Publication of EP0442844B1 publication Critical patent/EP0442844B1/fr
Application granted granted Critical
Publication of EP0442844B2 publication Critical patent/EP0442844B2/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • D06P3/14—Wool
    • 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
    • D06P3/14—Wool
    • D06P3/148—Wool using reactive 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
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/07—Organic amine, amide, or n-base containing
    • 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 new method for fiber and flat level dyeing of wool with reactive dyes, the material dyed by the new method and a means for carrying out the method.
  • the present method is particularly suitable for producing light to medium shades.
  • auxiliary mixture as component (c) can be a nonionic compound of the formula wherein R "is an alkyl or alkenyl radical having 12 to 22 carbon atoms and x and y are integers, the sum of x and y being 80 to 140.
  • auxiliary mixtures which comprise a compound of the formula (3a) as component (a) and a compound of the formula (4b) as component (b) or auxiliary mixtures which comprise a compound of the formula (3b) as component (a) and as a component (b) contain a compound of formula (4a).
  • M in the formulas (1), (3) and (4) denotes hydrogen, alkali metal, such as sodium, potassium and in particular ammonium.
  • the radicals Q, Q ', Q 1 and Q' 1 and A 8 , A ' 8 , A 1 ⁇ and A 2 8 in the formulas (1) and (3) are derived from quaternizing agents , QC 1 to C 4 -Alkyl, -CH 2 -CO-NH 2 , or is.
  • quaternizing agents are e.g. Acetyl bromides, ethyl bromides, ethylene chlorohydrin, ethylene bromohydrin, epichlorohydrin, epibromohydrin, dimethyl sulfate, diethyl sulfate and especially chloroacetamide.
  • the aliphatic radicals R 1 , R 2 , R 3 , R 4 , R 5 and R 6 in the formulas (1), (3) and (4) are alkyl or alkenyl radicals having 12 to 24, preferably 16 to 22, carbon atoms Consideration. Examples include: the n-dodecyl, myristyl, n-hexadecyl, n-heptadecyl, n-octadecyl, arachidyl, behenyl, dodecenyl, hexadecenyl, oleyl and octadecenyl radical.
  • the compounds of components (a), (b) and (c) are e.g. known (in part) from US-A-4,444,564.
  • the compounds of component (a) according to formula (1a) are prepared by adding 2 to 15 moles of ethylene oxide to aliphatic amines which have an aliphatic radical with 12 to 24 carbon atoms and optionally the adduct in the acidic monoester and optionally the acidic one Monoesters converted into the alkali or ammonium salts or reacting the adduct with one of the quaternizing agents mentioned above.
  • the connections of component (b) correspond Chend formula (1 b) are prepared by adding 25 to 200 mol of ethylene oxide onto aliphatic amines which have an aliphatic radical with 12 to 24 carbon atoms, and optionally the adduct in the acidic ester and optionally the acidic ester in the alkali or Converted ammonium salts or reacted the adduct with one of the quaternizing agents mentioned above.
  • the compounds of formula (2) are prepared by adding 80 to 140 moles of ethylene oxide to a compound of formula where R "has the meaning given under formula (2).
  • the amines which are required as starting materials for the preparation of the compounds of the formulas (1), (3) and (4) can have saturated or unsaturated, branched or unbranched hydrocarbon radicals having 12 to 24, preferably 16 to 22, carbon atoms.
  • the amines can be chemically uniform or in the form of mixtures.
  • the amine mixtures used are preferably those which arise when natural fats or oils, such as tallow fat, soybean or coconut oil, are converted into the corresponding amines.
  • Dodecylamine, hexadecylamine, octadecylamine, arachidylamine, behenylamine and octadecenylamine may be mentioned as amines.
  • Tallow fatty amine is a mixture of approx. 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 e.g. 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 adding bases such as ammonia, sodium or potassium hydroxide in a conventional manner.
  • An auxiliary mixture comprising 10 to 80 parts, preferably 20 to 70 parts of component (a), 5 to 70 parts, preferably 5 to 50 parts of component (b) and 0 to 70, preferably 0 to 50, is used for the process according to the invention
  • Parts of the compound of component (c) and ad contains 100 parts of water.
  • auxiliary mixture consisting of components (a), (b) and optionally (c) are added to the dyebath range from 0.5 to 4 percent by weight, based on the fiber material to be dyed. 1 to 2 percent by weight of the auxiliary mixture, based on the fiber material, is preferably used.
  • the weight ratio of components (a) and (b) is between 1: 5 and 10: 1, preferably between 1: 2 and 5: 1.
  • Wool can be considered as the fiber material that can be dyed according to the invention.
  • the fiber material can be in various forms. Examples include: flake, sliver, yarn, fabric, knitwear or carpets.
  • the wool can be finished normally or without felt.
  • dyes This class of dyes is referred to in the Color Index 3rd edition 1971 as "reactive dyes". These are predominantly those dyes which contain at least one group which is reactive with polyhydroxyl fibers (cellulose fibers) or polyamide fibers, in particular wool, a precursor for this or a substituent which is reactive with polyhydroxyl fibers or polyamide fibers.
  • Suitable bases for the reactive dyes are, in particular, those from the series of mono-, dis- or polyazo dyes including formazan dyes and anthraquinone, xanthene, nitro, triphenylmethane, naphthoquinonimine, dioxazine and phthalocyanine dyes, the azo and phthalocyanine dyes can be both metal-free and metal-containing.
  • Reactive groups and precursors which form such reactive groups include, for example, epoxy groups, the ethyleneimide group, the vinyl grouping in vinylsulfone or in acrylic acid residues and the ⁇ -sulfatoethylsulfone group, the ⁇ -chloroethylsulfone group or the ⁇ -dialkylaminoethylsulfone group.
  • the reactive substituents in reactive dyes are those which are easily removable and leave an electrophilic residue.
  • substituents are 1 or 2 halogen atoms in an aliphatic acyl radical, e.g. in the ⁇ -position or a- and ⁇ -position of a propionyl radical or in the a- and / or ⁇ -position of an acrylic acid radical, or 1 to 3 halogen atoms on the following ring system into consideration: pyridazine, pyrimidine, pyridazone, triazine, quinoxaline or phthalazine.
  • Dyes with two or more identical or different reactive groups can also be used.
  • Preferred reactive dyes contain chloroacetyl, bromoacrylic or dibromopropionyl as reactive substituents.
  • the reactive dyes can be acidic, salt-forming substituents, e.g. Contain carboxylic acid groups, sulfuric acid and phosphonic acid ester groups, phosphonic acid groups or preferably sulfonic acid groups.
  • Reactive dyes with at least one sulfonic acid group are preferred, in particular reactive dyes with an azo or anthraquinone base which preferably has two to three sulfonic acid groups.
  • Mixtures of reactive dyes can also be used, it being possible to produce bichromatic or trichromatic dyes.
  • the coloring takes place after the pull-out procedure.
  • the amount of dyes added to the dye liquor depends on the desired color strength. In general, amounts of 0.01 to 10 percent by weight, preferably 0.01 to 2 percent by weight, based on the fiber material used, have proven successful.
  • the liquor ratio can be chosen within a wide range e.g. 1: 3 to 1: 100, preferably 1: 8 to 1:30.
  • the dye baths can contain mineral acids, e.g. Sulfuric acid or phosphoric acid, organic acids, suitably contain aliphatic carboxylic acids such as formic acid, acetic acid, oxalic acid or citric acid and / or salts such as ammonium acetate, ammonium sulfate or sodium acetate.
  • mineral acids e.g. Sulfuric acid or phosphoric acid
  • organic acids suitably contain aliphatic carboxylic acids such as formic acid, acetic acid, oxalic acid or citric acid and / or salts such as ammonium acetate, ammonium sulfate or sodium acetate.
  • the acids are used primarily to adjust the pH of the liquors used according to the invention, which is between 4 and 5.
  • the dye liquors can also contain other additives, e.g. Wool protection, dispersing and wetting agents as well as defoamers included.
  • the usual dyeing apparatuses such as, for example, open baths, combed, strand yarn or packing apparatuses, jiggers, paddle apparatuses, tree dyeing apparatuses, circulation or jet dyeing apparatuses or reel runners can be used.
  • the dyeing is advantageously carried out at a temperature in the range from 60 to 120 ° C., preferably from 70 to 105 ° C.
  • the dyeing time is within the usual range and is generally 20 to 120 minutes.
  • the dyeing process can be followed by an alkaline after-treatment, e.g. with aqueous ammonia, alkali metal hydroxides, alkali metal carbonates, bicarbonates or hexamethylenetetraamine.
  • the pH of the dye baths containing alkali is expediently 7.5 to 9, preferably 8 to 8.5.
  • the dyeing of the fiber material is expediently carried out in such a way that the material to be dyed with an aqueous liquor which contains the acid, the auxiliary mixture of components (a) and (b) and, if appropriate, component (c) and a temperature of 30 to 60 ° C, treated briefly and adding the reactive dye to the same bath.
  • the temperature is then slowly increased in order to dye in a range from 80 to 100 ° C. and for 20 to 90 minutes, preferably 30 to 60 minutes.
  • the material to be dyed is then treated for a further 10 to 20 minutes at 70 to 90 ° C. after the addition of alkalis, preferably sodium hydrogen carbonate or sodium carbonate. Finally, the colored material is pulled out and rinsed, acidified and dried as usual.
  • the dyeing process according to the invention gives fiber and flat dyeings, especially in light to medium shades with good light and wet fastness properties.
  • the pH of the liquor is 4.5.
  • the 12 mg of the dye of the formula 24 mg of the dye of the formula and 44 mg of the dye of the formula contains, the dyebath is kept at 40 ° for about 5 minutes and then heated to 60 at a rate of 1 ° / min and held at 60 ° for 20 minutes. The mixture is then heated to 98 at 1 ° / min and dyed for 30 minutes. After the liquor has cooled to 70, it is rinsed as usual. A fiber-uniform and flat-level dyeing with good fastness properties is obtained.
  • EXAMPLE 3 The procedure is as described in Example 1 with the difference that 0.2 g of the adduct of 34 moles of ethylene oxide and 1 mole of a C 2 oC 22 fatty amine is used instead of auxiliary B 2 . A fiber- and flat-level dyeing with good fastness properties is obtained.
  • EXAMPLE 4 The procedure is as described in Example 1, with the difference that, instead of auxiliary B 2, 0.2 g of the quaternized adduct of 34 mol of ethylene oxide and 1 mol of a C 2 oC 22 fatty amine is used. A fiber- and flat-level dyeing with good fastness properties is obtained.
  • EXAMPLE 5 The procedure is as described in Example 1, with the difference that 0.2 g of the adduct of 30 mol of ethylene oxide and 1 mol of tallow fatty amine is used instead of B 2 . A fiber- and flat-level dyeing with good fastness properties is obtained.
  • EXAMPLE 9 The procedure is as described in Example 2, with the difference that, instead of the dye mixture, 80 mg of the dye of the formula is used.
  • EXAMPLE 10 The procedure is as described in Example 9, with the difference that instead of 80 mg of the dye of the formula (105), 80 mg of the dye of the formula starts.
  • EXAMPLE 11 The procedure is as described in Example 9, with the difference that instead of 80 mg of the dye of the formula (105), 200 mg of the dye of the formula used.
  • EXAMPLE 12 The procedure is as described in Example 9, with the difference that instead of 80 mg of the dye of the formula (105), 320 mg of the dye of the formula used.
  • EXAMPLE 13 The procedure is as described in Example 9, with the difference that instead of 80 mg of the dye of the formula (105), 100 mg of the dye of the formula used.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)

Claims (15)

1. Procédé pour teindre uniformément, tant au niveau des fibres qu'au niveau du tissu, de la laine avec des colorants réactifs en présence d'un mélange d'adjuvants, caractérisé en ce que l'on utilise pour la teinture de ces matériaux un bain aqueux contenant au moins un colorant réactif et un mélange d'adjuvants contenant, comme composant (a), au moins un composé de formule
Figure imgb0055
et, comme composant (b), au moins un composant de formule
Figure imgb0056
dans laquelle
R1 et R2 représentent indépendamment un résidu aliphatique comportant de 12 à 24 atomes de carbone,
Q et Q' représentent indépendamment un groupe alkyle en C1-4,
-CH2-CO-NH2, -CH2-CH(OH)-CH2CI ou -CH2-CH(OH)CI, A- et A'- représente un anion,
Z1, Z2 Z'1 et Z'2 représentent indépendamment un atome d'hydrogène, un groupe S03M ou P03M, M étant un atome d'hydrogène, un métal alcalin ou un groupe ammonium, t1 est égal à 0 ou 1 et t2 est égal à 0 ou 1, où, lorsque t1 est égal à 0, Z1 et Z2 représentent un atome d'hydrogène ou un des deux représente un atome d'hydrogène et l'autre un groupe S03M ou P03M, et lorsque t2 est égal à 0, Z'1 et Z'2 représentent un atome d'hydrogène ou un des deux représente un atome d'hydrogène et l'autre un groupe S03M ou P03M,
mi, ni, p1 et q1 sont des nombres entiers, la somme de (m1 + n1) étant comprise entre 2 et 15 et la somme de (p1 + q1) entre 25 et 200,

et la teinture est terminée, indépendamment de l'intensité de couleur, à un pH compris entre 4,0 et 5,0.
2. Procédé conforme à la revendication 1, caractérisé en ce que la laine est teinte en des nuances claires à moyennement foncées.
3. Procédé conforme à une des revendications 1 à 2, caractérisé en ce que la somme (mi + n1) est comprise entre 5 et 12 et la somme de (p1 + q1) entre 25 et 100.
4. Procédé conforme à une des revendications 1 à 3, caractérisé en ce que le mélange d'adjuvant contient en plus, comme composant (c), un composé non ionogène de formule
Figure imgb0057
dans laquelle R" représente un radical alkyle ou alcényle comportant de 12 à 22 atomes de carbone et x et y sont des nombres entiers, la somme de x + y étant comprise entre 80 et 140.
5. Procédé conforme à une des revendications 1 à 4, caractérisé en ce que l'on utilise un mélange d'adjuvants contenant, comme composant (a), un composé de formule
Figure imgb0058
comme composant (b), un composé de formule
Figure imgb0059
et, comme composant (c), un composé de formule (2), dans lesquelles R3 et R4 représentent indépendamment l'un de l'autre un résidu aliphatique comportant de 12 à 24 atomes de carbone,
Q1 et Q'1 représentent indépendamment un groupe alkyle en C1-4, ou un groupe -CH2-CO-NH2,
Z3, Z4 Z'3 et Z'4 représentent indépendamment un atome d'hydrogène ou un groupe S03M, M étant un atome d'hydrogène, un métal alcalin ou un groupe ammonium,
m2, n2, p2 et q2 sont des nombres entiers, la somme de (m2 +n2) étant comprise entre 5 et 12 et la somme de (p2 + q2) entre 25 et 100, et
A1- et A2- représentent un anion.
6. Procédé conforme à une des revendications 1 à 4, caractérisé en ce que l'on utilise un mélange d'adjuvants contenant, comme composant (a), un composé de formule
Figure imgb0060
et, comme composant (b), un composé de formule
Figure imgb0061
dans lesquelles R5 et R6 représentent indépendamment l'un de l'autre un résidu aliphatique comportant de 12 à 24 atomes de carbone, Z5 et Z6 représentent un atome d'hydrogène ou un des deux représente un atome d'hydrogène et l'autre un groupe S03M,
Z's et Z'6 représentent indépendamment un atome d'hydrogène ou un groupe S03M, M étant un atome d'hydrogène, un métal alcalin ou un groupe ammonium, et
ma, n3, p3 et q3 étant des nombres entiers, la somme de (m3 + n3) étant comprise entre 5 et 12 et la somme de (p3 + q3) étant comprise entre 25 et 100.
7. Procédé conforme à une des revendications 1 à 4, caractérisé en ce que l'on utilise un mélange d'adjuvants contenant, comme composant (a), un composé de formule (3a) conforme à la revendication 5 et, comme composant (b), un composé de formule (4b) conforme à la revendication 6.
8. Procédé conforme à une des revendications 1 à 4, caractérisé en ce que l'on utilise un mélange d'adjuvants contenant, comme composant (a), un composé de formule (3b) conforme à la revendication 5 et, comme composant (b), un composé de formule (4a) conforme à la revendication 6.
9. Procédé conforme à une des revendications 1 à 8, caractérisé en ce que l'on utilise un mélange d'adjuvants contenant
de 10 à 80 parties du composant (a),
de 5 à 70 parties du composant (b) et
de 0 à 70 parties du composant (c) et

une quantité suffisante d'eau pour arriver à 100 parties.
10. Procédé conforme à une des revendications 1 à 9, caractérisé en ce que les composants (a) et (b) sont présents en un rapport en poids compris entre 1/5 et 10/1.
11. Procédé conforme à une des revendications 1 à 10, caractérisé en ce que l'on utilise des colorants réactifs contenant au moins un groupe sulfo.
12. Procédé conforme à la revendication 11, caractérisé en ce que l'on utilise des colorants réactifs contenant, comme substituants réactifs, des résidus chloroacétyle, bromoacétyle ou dibromopropionyle.
13. Procédé conforme à une des revendications 1 à 12, caractérisé en ce que l'on teint à une température comprise entre 60 et 120 ° C.
14. Procédé conforme à une des revendications 1 à 13, caractérisé en ce que l'on teint avec un rapport de bain compris entre 1/3 et 1/100, de préférence entre 1/8 et 1/30.
15. Mélange d'adjuvants de teinture contenant, comme composant (a), de 10 à 80 parties du composé de formule
Figure imgb0062
comme composant (b), de 5 à 7 parties du composé de formule
Figure imgb0063
dans laquelle
R1 et R2 représentent indépendamment un résidu aliphatique comportant de 12 à 24 atomes de carbone,
Q et Q' représentent indépendamment un groupe alkyle en C1-4,
-CH2-CO-NH2, -CH2-CH(OH)-CH2CI ou -CH2-CH(OH)CI,
A- et A'- représente un anion,
Z1, Z2 Z'1 et Z'2 représentent indépendamment un atome d'hydrogène, un groupe S03M ou P03M, M étant un atome d'hydrogène, un métal alcalin ou un groupe ammonium, t1 est égal à 0 ou 1 et t2 est égal à 0 ou 1, où, lorsque t1 est égal à 0, Z1 et Z2 représentent un atome d'hydrogène ou un des deux représente un atome d'hydrogène et l'autre un groupe S03M ou P03M, et lorsque t2 est égal à 0, Z'1 et Z'2 représentent un atome d'hydrogène ou un des deux représente un atome d'hydrogène et l'autre un groupe S03M ou P03M, mi, ni, p1 et q1 sont des nombres entiers, la somme de (m1 + n1) étant comprise entre 2 et 15 et la somme de (p1 + q1 ) entre 25 et 200,

et, comme composant (c), de 0 à 70 parties du composé de formule (2)
Figure imgb0064
dans laquelle R" représente un résidu alkyle ou alcényle comportant de 12 à 22 atomes de carbone et x et y sont des nombres entiers, la somme de x et y étant comprise entre 80 et 140.
EP91810078A 1990-02-14 1991-02-05 Procédé de teinture de la laine avec des colorants réactifs Expired - Lifetime EP0442844B2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH47790 1990-02-14
CH477/90 1990-02-14

Publications (3)

Publication Number Publication Date
EP0442844A1 EP0442844A1 (fr) 1991-08-21
EP0442844B1 true EP0442844B1 (fr) 1995-02-01
EP0442844B2 EP0442844B2 (fr) 1998-01-21

Family

ID=4187901

Family Applications (1)

Application Number Title Priority Date Filing Date
EP91810078A Expired - Lifetime EP0442844B2 (fr) 1990-02-14 1991-02-05 Procédé de teinture de la laine avec des colorants réactifs

Country Status (9)

Country Link
US (1) US5145486A (fr)
EP (1) EP0442844B2 (fr)
JP (1) JPH04214476A (fr)
KR (1) KR910015749A (fr)
AU (1) AU638793B2 (fr)
CA (1) CA2036224A1 (fr)
DE (1) DE59104446D1 (fr)
ES (1) ES2067902T5 (fr)
NZ (1) NZ237087A (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0548013A1 (fr) * 1991-12-16 1993-06-23 Ciba-Geigy Ag Procédé de teinture de la laine avec l'aide d'un pétraitement avec un plasma basse température ou Corona
IT1261839B (it) * 1992-08-03 1996-06-03 Sandoz Ag Procedimento per la produzione di effetti speciali di coloritura su prodotti tessili e miscele di coloranti impiegate.
ES2141211T3 (es) * 1993-07-28 2000-03-16 Ciba Sc Holding Ag Procedimiento para el teñido de materiales de fibras que contienen lana.
DE19848894A1 (de) * 1998-10-23 2000-04-27 Bayer Ag Phosphorsäureester
MXPA05013495A (es) * 2003-06-26 2006-03-09 Ciba Sc Holding Ag Composiciones liquidas acuosas de ciclodextrina o derivados de ciclodextrina y proceso que usa dichas composiciones.
EP1777337A1 (fr) * 2005-10-07 2007-04-25 Clariant International Ltd. Procédé pour la teinture de fibres de polyamide
DE102008058921A1 (de) * 2008-11-25 2010-05-27 Henkel Ag & Co. Kgaa Neue Färbemittel

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3919283A (en) * 1965-03-18 1975-11-11 Ciba Geigy Ag Sulfate derivatives of polyglycol compounds
DE2847913B1 (de) * 1978-11-04 1980-02-07 Hoechst Ag Verfahren zum Faerben von Wolle mit Reaktivfarbstoffen
DE3363011D1 (en) * 1982-03-12 1986-05-22 Ciba Geigy Ag Process for dyeing fibrous material from natural polyamides
FR2574791A1 (fr) * 1984-12-14 1986-06-20 Sandoz Sa Sulfates d'amines grasses, leur preparation et leur utilisation comme produits auxiliaires
DE3872824D1 (de) * 1987-10-14 1992-08-20 Ciba Geigy Ag Verfahren zum faerben von natuerlichen polyamidfasern mit reaktivfarbstoffen.
EP0414631A1 (fr) * 1989-02-22 1991-02-27 Ciba-Geigy Ag Mélange d'agents auxiliaires et son utilisation pendant la teinture de matériaux fibreux en polyesters
EP0417040A1 (fr) * 1989-09-06 1991-03-13 Ciba-Geigy Ag Procédé pour teindre la laine

Also Published As

Publication number Publication date
CA2036224A1 (fr) 1991-08-15
NZ237087A (en) 1993-04-28
JPH04214476A (ja) 1992-08-05
EP0442844B2 (fr) 1998-01-21
ES2067902T3 (es) 1995-04-01
EP0442844A1 (fr) 1991-08-21
AU638793B2 (en) 1993-07-08
ES2067902T5 (es) 1998-04-16
US5145486A (en) 1992-09-08
KR910015749A (ko) 1991-09-30
DE59104446D1 (de) 1995-03-16
AU7099491A (en) 1991-08-15

Similar Documents

Publication Publication Date Title
EP0089004B1 (fr) Procédé de teinture de matière fibreuse de polyamides naturels
EP0074923B1 (fr) Adjuvant de teinture et son utilisation dans la teinture ou l'impression de matériaux en fibres de polyamide synthétique
EP0135198B1 (fr) Procédé de teinture de matière fibreuse en polyamides synthétiques
DE1940178A1 (de) AEthansulfonsaeurederivate
EP0197005B1 (fr) Hémiesters d'acide maléique ou d'acide phtalique et d'amines grasses alkoxylées
EP0442844B1 (fr) Procédé de teinture de la laine avec des colorants réactifs
EP0309405B1 (fr) Procédé de teinture ou d'impression de matières fibreuses en polyamides naturels ou synthétiques avec des colorants réactifs
EP0312493B1 (fr) Procédé de teinture de fibres en polyamide naturelles avec des colorants réactifs
DE1924765B2 (de) Polyoxyalkylierte Amine und deren Verwendung beim Färben mit Reaktivfarbstoffen
EP0235088B1 (fr) Hémi-esters d'acide maléique ou phthalique et d'amines grasses alkoxylées
EP0745720B1 (fr) Utilisation des préparations d'agents auxiliaires pour la teinture de la laine
EP0163608B1 (fr) Procédé de teinture de matières fibreuses en polyamides naturelles ou synthétiques avec des colorants à complexes métallifères 1:1
EP0225282B1 (fr) Procédé de post-traitement de matière fibreuse cellulosique teinte
EP0593392B1 (fr) Procédé de teinture de fibres polyamides naturelles et synthétiques avec des mélanges de colorants
EP0302013A1 (fr) Procédé de teinture de produits textiles en polyamide
EP0474594B1 (fr) Procédé de teinture de la laine et ses mélanges avec d'autres fibres avec des colorants réactifs
EP0040780A1 (fr) Procédé d'impression de matière fibreuse synthétique hydrophobe
EP0264346B1 (fr) Procédé de teinture de matières fibreuses en polyamides naturels ou synthétiques avec des colorants à complexes métallifères 1:1
DE2841800C2 (fr)
EP1123300A1 (fr) Esters d'acide phosphorique
DE1568258C3 (de) Verwendung von amphoteren Polyglykolverbindungen als Egalisiermittel
DE2405057C3 (de) Verfahren zum Klotzfärben oder Bedrucken von Textilmischmaterial aus Cellulose- und Polyesterfasern
DE1901165A1 (de) N-Alkyl-aminoalkansulfonsaeuren
DE1901411A1 (de) Verfahren zum kontinuierlichen Faerben von Polyester-Textilmaterialien
DE2710898A1 (de) Verfahren zum kontinuierlichen faerben von synthetischen und natuerlichen polyamiden und hilfsmittel dazu

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19910207

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): BE CH DE ES FR GB IT LI

17Q First examination report despatched

Effective date: 19930622

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): BE CH DE ES FR GB IT LI

ET Fr: translation filed
REF Corresponds to:

Ref document number: 59104446

Country of ref document: DE

Date of ref document: 19950316

REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2067902

Country of ref document: ES

Kind code of ref document: T3

ITF It: translation for a ep patent filed
GBT Gb: translation of ep patent filed (gb section 77(6)(a)/1977)

Effective date: 19950314

PLBI Opposition filed

Free format text: ORIGINAL CODE: 0009260

26 Opposition filed

Opponent name: BAYER AG, LEVERKUSEN KONZERNVERWALTUNG RP PATENTE

Effective date: 19951027

PLBF Reply of patent proprietor to notice(s) of opposition

Free format text: ORIGINAL CODE: EPIDOS OBSO

ITTA It: last paid annual fee
PLBF Reply of patent proprietor to notice(s) of opposition

Free format text: ORIGINAL CODE: EPIDOS OBSO

PLBF Reply of patent proprietor to notice(s) of opposition

Free format text: ORIGINAL CODE: EPIDOS OBSO

PLBF Reply of patent proprietor to notice(s) of opposition

Free format text: ORIGINAL CODE: EPIDOS OBSO

REG Reference to a national code

Ref country code: CH

Ref legal event code: PUE

Owner name: CIBA-GEIGY AG TRANSFER- CIBA SC HOLDING AG

BECN Be: change of holder's name

Effective date: 19961129

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: ES

Payment date: 19970214

Year of fee payment: 7

REG Reference to a national code

Ref country code: FR

Ref legal event code: TP

Ref country code: CH

Ref legal event code: PFA

Free format text: CIBA SC HOLDING AG TRANSFER- CIBA SPECIALTY CHEMICALS HOLDING INC.

RAP2 Party data changed (patent owner data changed or rights of a patent transferred)

Owner name: CIBA SPECIALTY CHEMICALS HOLDING INC.

PLAW Interlocutory decision in opposition

Free format text: ORIGINAL CODE: EPIDOS IDOP

REG Reference to a national code

Ref country code: GB

Ref legal event code: 732E

PLAW Interlocutory decision in opposition

Free format text: ORIGINAL CODE: EPIDOS IDOP

PUAH Patent maintained in amended form

Free format text: ORIGINAL CODE: 0009272

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 19971223

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19980108

Year of fee payment: 8

Ref country code: CH

Payment date: 19980108

Year of fee payment: 8

27A Patent maintained in amended form

Effective date: 19980121

AK Designated contracting states

Kind code of ref document: B2

Designated state(s): BE CH DE ES FR GB IT LI

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 19980121

Year of fee payment: 8

REG Reference to a national code

Ref country code: CH

Ref legal event code: AEN

Free format text: AUFRECHTERHALTUNG DES PATENTES IN GEAENDERTER FORM

ITF It: translation for a ep patent filed
GBTA Gb: translation of amended ep patent filed (gb section 77(6)(b)/1977)
REG Reference to a national code

Ref country code: FR

Ref legal event code: CD

ET3 Fr: translation filed ** decision concerning opposition
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 19980403

Year of fee payment: 8

REG Reference to a national code

Ref country code: ES

Ref legal event code: DC2A

Kind code of ref document: T5

Effective date: 19980310

REG Reference to a national code

Ref country code: ES

Ref legal event code: PC2A

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19990205

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: ES

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19990206

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LI

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19990228

Ref country code: CH

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19990228

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19990228

BERE Be: lapsed

Owner name: CIBA SPECIALTY CHEMICALS HOLDING INC.

Effective date: 19990228

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 19990205

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19991029

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19991201

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

REG Reference to a national code

Ref country code: ES

Ref legal event code: FD2A

Effective date: 20010503

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES;WARNING: LAPSES OF ITALIAN PATENTS WITH EFFECTIVE DATE BEFORE 2007 MAY HAVE OCCURRED AT ANY TIME BEFORE 2007. THE CORRECT EFFECTIVE DATE MAY BE DIFFERENT FROM THE ONE RECORDED.

Effective date: 20050205