EP1863972A2 - Procede pour teindre des textiles avec un colorant de cuve - Google Patents

Procede pour teindre des textiles avec un colorant de cuve

Info

Publication number
EP1863972A2
EP1863972A2 EP06725204A EP06725204A EP1863972A2 EP 1863972 A2 EP1863972 A2 EP 1863972A2 EP 06725204 A EP06725204 A EP 06725204A EP 06725204 A EP06725204 A EP 06725204A EP 1863972 A2 EP1863972 A2 EP 1863972A2
Authority
EP
European Patent Office
Prior art keywords
different
same
vat
range
vat dye
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.)
Withdrawn
Application number
EP06725204A
Other languages
German (de)
English (en)
Inventor
Karl Siemensmeyer
Heinz Heissler
Ursula Krieg
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 SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of EP1863972A2 publication Critical patent/EP1863972A2/fr
Withdrawn legal-status Critical Current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
    • 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
    • D06P1/22—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 vat dyestuffs including indigo
    • 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
    • D06P1/613—Polyethers without nitrogen
    • D06P1/6131—Addition products of hydroxyl groups-containing compounds with oxiranes
    • D06P1/6135—Addition products of hydroxyl groups-containing compounds with oxiranes from aromatic alcohols or from phenols, naphthols
    • 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
    • D06P1/62—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 low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic groups
    • D06P1/621—Compounds without nitrogen
    • D06P1/622—Sulfonic acids or their salts

Definitions

  • the present invention relates to a process for dyeing textile with one or more vat dyes, characterized in that uncolored textile treated with an aqueous liquor containing
  • R 1 selected from hydrogen, phenyl, CH (CH 3 ) C 6 H 5 and C 1 -C 10 -AlkVl
  • R 2 is the same or different and selected from hydrogen, phenyl and
  • AO alkylene oxide
  • EO ethylene oxide
  • a is the same or different and selected from numbers ranging from O to 150
  • b are the same or different and selected from numbers in the range of 15 to 250
  • d is the same or different and selected from zero and one
  • M is the same or different and selected from alkali metals.
  • vat dye in its reduced form often called leuco form
  • the reduced form of the vat dye is reoxidized with, for example, air or hydrogen peroxide (H 2 O 2 ) to recover the poorly or not at all water soluble form of the vat dye concerned, now on the fiber.
  • vat dye in its oxidized form by means of a forced application to textile, for example in continuous dyeing processes by padding, and then to pull the textile with the caked vat dye first through a reduction bath and then to reoxidize.
  • leveling agents such as, for example, fatty alcohol sulfonates, oleic acid ethoxylates or naphthalenesulfonic acid-formaldehyde condensation products.
  • leveling agents such as, for example, fatty alcohol sulfonates, oleic acid ethoxylates or naphthalenesulfonic acid-formaldehyde condensation products.
  • affinity of dye in reduced form degrades to the fiber and that one obtains poorer dye yields.
  • vat dye which is not applied to the fiber precipitates as a poorly soluble substance after reoxidation and can be recovered by working up the liquor, but additional work is necessary for this purpose.
  • vat dye dyed textile which has particularly good coloration and in particular a low tendency to form a ring dye.
  • Textile is to be understood as meaning one-, two- or three-dimensional substrates made of textile material, for example fibers, yarns, threads, knitwear, woven fabric, nonwovens and fabricated goods made of cellulosic material, for example cotton, jute, flax, hemp and ramie and cotton blended fabric with polyester, modified polyester, polyamide, polyacrylonitrile, triacetate, acetate, polycarbonate, polypropylene, polyvinyl chloride, viscose, silk. Also suitable are cellulose-containing substrates such as paper, in particular filter paper, cardboard and cardboard.
  • non-dyed textile is used to carry out the process according to the invention.
  • cotton blend fabric with polyester
  • Uncoloured textile may be bleached, for example with hydrogen peroxide or with chlorine bleach.
  • undyed textile is dyed with several or preferably one vat dye. If one wishes to dye unstained textile with a plurality of, for example, two vat dyes, then the second and optionally further vat dyes are used as shading dyes, i. their proportion is less than 5% by weight, based on the first vat dye.
  • textile is treated with an aqueous liquor containing
  • Suitable vat dyes (a) are in particular
  • Suitable reducing agents (b) are, for example, NaHSO 3 , Na 2 S 2 O 4 , NaO 2 S-CH 2 OH (sodium hydroxymethanesulfinate), hydroxyacetone and boron hydrides, for example NaBH 4 and combinations of the aforementioned reducing agents; Furthermore, it is possible to use a cathode as a reducing agent (b) and perform the reduction electrochemically, for example with iron salts as electron mediator. Particularly preferred is the use of at least one weaker reducing agent, for example hydroxyacetone, followed by at least one stronger reducing agent such as Na 2 S 2 O 4 .
  • vat dye (a) and reducing agent (b) can be any suitable vat dye (a) and reducing agent (b).
  • vat dye in reduced form (leuco form), either in the leuco form as such or as Leukoküpenfarbstoffester, especially as esters of sulfuric acid.
  • vat dye (a), reducing agent (b) and vat dye in reduced form (a 1 ).
  • the liquor used to carry out the process according to the invention contains at least one compound of the general formula I a or I b,
  • R 1 is selected from hydrogen, phenyl, CH (CH 3 ) C 6 H 5 and
  • C 1 -C- J 0 -AlkVl branched or unbranched, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, iso- Pentyl, sec-pentyl, neo-pentyl, 1, 2-dimethylpropyl, iso-amyl, n-hexyl, iso-hexyl, sec-hexyl, n-butyl, n-octyl, 2-ethylhexyl, n- nonyl, n-decyl, more preferred C r C 4 alkyl such as methyl, ethyl, n-propyl, n-butyl and in particular iso-propyl, R 2 is the same or different and selected from hydrogen, phenyl and
  • C r Cio-alkyl branched or unbranched such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl, sec Pentyl, neo-pentyl, 1,2-dimethylpropyl, iso-amyl, n-hexyl, iso-hexyl, sec-hexyl, n-butyl, n-octyl, 2-ethylhexyl, n-nonyl, n -Decyl, more preferably C r C 4 alkyl as
  • AO is alkylene oxide, identical or different, preferably C 3 -C 5 -alkylene oxide, for example butylene oxide, pentylene oxide and in particular propylene oxide (C 3 H 6 O),
  • EO is ethylene oxide, (CH 2 CH 2 O),
  • a is different or preferably the same and selected from numbers in the range from 0 to 150, preferably up to 20, where a as the mean (number average) can also be a non-integer number,
  • b is different or preferably the same and selected from numbers in the range from 15 to 250, preferably 20 to 200 and particularly preferably to 35, where b as average (number average) can also be a non-integer number,
  • d is the same or different and chosen from zero and one
  • M is the same or different and selected from alkali metals, for example lithium, cesium, rubidium and preferably sodium and potassium.
  • the process according to the invention can be carried out continuously or batchwise.
  • the process according to the invention is carried out at a liquor length in the range from 1: 4 to 1: 100, preferably in the range from 1: 5 to 1: 20.
  • the inventive method is carried out at a temperature in the range of 20 to 90 0 C, preferably in the range of 40 to 70 0 C, more preferably in the range of 50 to 70 ° C.
  • the process according to the invention is carried out at a pH in the range from 8 to 14, preferably in the range from 11 to 14.
  • the process according to the invention can be carried out, for example, at atmospheric pressure.
  • liquors used in the process of the invention range from 0.000001 to 50, preferably from 0.0001 to 20% by weight of vat dye (a), by weight of textile to be dyed, in the range of from 1 to 100 g / l liquor, preferably in the range of 2 to 50 g / l liquor reducing agent (b), and in the range of 0.00001 to 200 wt .-%, preferably 0.0001 to 100 wt .-%, most preferably between 0 , 0001 and 50 wt .-% compound of general formula I a or I b, based on vat dye (a).
  • 0.0001 to 100% by weight of compound of the formula I a or I b, based on vat dye (a) or vat dye in reduced form (a 1 ), are used.
  • Suitable oxidizing agents are, for example, oxygen, in particular atmospheric oxygen, furthermore hydrogen peroxide, 3-nitrobenzenesulfonic acid, 2-nitrobenzenesulfonic acid, 4-nitrobenzenesulfonic acid or 2,4-dinitrobenzenesulfonic acid or 2-nitrobenzoic acid, 3-nitrobenzoic acid, 4-nitrobenzoic acid or 2,4 Dinitrobenzoic acid as the free acid or, preferably, as the salt, for example as the alkali metal salt, especially as the sodium salt, and perborates, especially sodium perborate, sodium percarbonate.
  • the oxidation is carried out at a basic pH, for example in the range from 8 to 14, preferably 10 to 14.
  • oxidizing agent to the liquor containing vat dye (a), reducing agent (b) or reduced vat dye (a 1 ) and at least one compound of general formula Ia or I b.
  • the liquor containing vat dye (a), reducing agent (b) or reduced vat dye (a 1 ) and at least one compound of general formula Ia or I b according to To replace the invention treatment against a liquor containing one or more oxidizing agents.
  • At least one additional auxiliary (d) is added to the treatment according to the invention before the oxidation, for example when preparing the liquor used in the process according to the invention, the vat dye (a), reducing agent (b) or reduced vat dye (a 1 ) and at least one compound of general formula Ia or I b contains.
  • Suitable auxiliaries (d) are, for example, amines, diamines, triamines, tetramines and polyamines, which may be low molecular weight or high molecular weight.
  • Preferred triamines and tetramines are, for example, H 2 N-CH 2 CH 2 -NH-CH 2 CH 2 NH 2 and H 2 N- (CH 2 CH 2 -NH) 2 -CH 2 CH 2 NH 2 .
  • Mixtures of H 2 N-CH 2 CH 2 -NH-CH 2 CH 2 NH 2 and H 2 N- (CH 2 CH 2 -NH) 2 -CH 2 CH 2 NH 2 are also suitable.
  • Preferred polyamines are, for example, polyethylenimine, for example with molecular weights M w in the range from 2000 to 20,000 g / mol, polyvinylpyrrolidone, for example with molecular weights M w in the range from 2000 to 20,000 g / mol, polyvinylimidazole, for example with molecular weights M w in the range from 2000 to 20,000 g / mol, preferably random polyvinylpyrrolidone-polyvinylimidazole copolymers, for example having molecular weights M w in the range from 2000 to 20,000 g / mol, and graft copolymers obtainable by grafting on comonomers containing nitrogen-containing heterocycles on polyal - Kylenglykol, in particular polyethylene glycol, for example, with molecular weights M w in the range of 250 to 2500 g / mol.
  • auxiliaries (d) are those graft copolymers whose preparation is grafted onto polyalkylene glycol, in particular polyethylene glycol, for example with molecular weights M w in the range from 250 to 2500 g / mol, at least two monomers, one of which is selected from Vinylpyrrolidone, N-vinyl- ⁇ -valerolactam and N-vinyl- ⁇ -caprolactam called, with N-vinylpyrrolidone is preferred, and the other is selected from the group of vinylated pyrroles, pyrrolidines, pyridines, quinolines, isoquinolines, purines, pyrazoles, Imidazoles, triazoles, tetrazoles, indolizines, pyridazines, pyrimidines, pyrazines, indoles, isoindoles, oxazoles, oxazolidones, oxazolidines, morpholines, pipe
  • auxiliaries (d) are organic phosphorus compounds, preferably C r Cio-alkyl phosphonates, preferably ethylphosphonate.
  • auxiliaries (d) are polyunsaturated, for example, three to 100-fold alcoxylated C 1 -C 20 -carboxylic acids, in particular three to 100-times ethoxylated fatty acids selected from, for example, stearic acid, oleic acid and linolenic acid.
  • auxiliary agents (d) are used for carrying out the process according to the invention.
  • the process according to the invention is carried out by first treating undyed textile with a liquor under the conditions described above, the vat dye (a), reducing agent (b) or reduced vat dye (a 1 ) and at least one Compound of the general formula contains Ia or I b, exchanges the fleet and treated with another fleet, containing, for example, at least one auxiliary (d). Thereafter, one exchanges the liquor containing at least one adjuvant (d), against another liquor containing at least one oxidizing agent, or performs an oxidation with air.
  • Suitable secondary saponifying agents are, for example, ammonium salts, in particular alkanolammonium salts of C 1 -C 4 -alkylbenzenesulfonic acids, amines, diamines and polyamines. Very suitable are after-sifting agents, as described, for example, in WO 04/50982, and the conditions described in the above-mentioned application.
  • aftersoaping can be in addition to one or more of the aforementioned Aftersoaping one or more nonionic Tensi- de insert such as one or more Cio-C 30 -Alkanolethoxylate, in particular of the formula ⁇ C 10 -C 30 -alkyl-O- (CH 2 - CH 2 O) W -H, where w is a number in the range of 3 to 100.
  • one or more nonionic Tensi- de insert such as one or more Cio-C 30 -Alkanolethoxylate, in particular of the formula ⁇ C 10 -C 30 -alkyl-O- (CH 2 - CH 2 O) W -H, where w is a number in the range of 3 to 100.
  • Another object of the present invention are textiles dyed by the method according to the invention.
  • Inventive textiles have no or none Significant discoloration, in particular no tendency to form a ring dyeing undesirable in many cases. Furthermore, good fastness properties are observed, for example good friction and washing fastnesses.
  • Another object of the present invention are aqueous liquors containing
  • Aqueous liquors of the invention are obtainable, for example, by mixing water with one or more vat dyes (a), one or more reducing agents (b) or (a 1 ) at least one vat dye in reduced form (leuco form), one or more compounds of the general formula I a or I b and optionally at least one auxiliary (d), wherein the order of addition of water, one or more vat dyes (a), one or more reducing agents (b) or (a 1 ) at least one vat dye in a reduced form (Leuko - Form), one or more compounds of general formula I a or I b and optionally at least one adjuvant (d) is arbitrary.
  • the preparation of compounds of the general formula Ia and Ib is known per se and is achieved, for example, by reacting phenols of the general formula IIa
  • sulfating reagents in particular sulfur trioxide or chlorosulfonic acid
  • aqueous alkali metal hydroxide for example with aqueous potassium hydroxide solution or in particular aqueous sodium hydroxide solution.
  • sulfating reagents in particular sulfur trioxide or chlorosulfonic acid
  • Naphthalenesulfonic acid-formaldehyde condensate having a molecular weight M w of 6,000 g / mol (comparative experiment VF.2)
  • Naphthalenesulfonic acid-formaldehyde condensate having a molecular weight M w of 16,000 g / mol (comparative experiment VF.3), or waived the use of additional substances (c) (comparative experiment VF.4).
  • the thus dyed cotton knitted fabric was then soaped with an aqueous treatment liquor of 1 ml / l of a 60% by weight aqueous solution of the diethanolamine salt of para-n-CgH ! 9-C 6 H 4 -SO 3 H and 0.5 g / l sodium carbonate for 15 min at 98 ° C in a liquor ratio of 1:20 after. Subsequently, the dyed cotton knitted fabric thus obtainable was dried at room temperature and the color obtained was assessed colorimetrically.
  • Flask F.8 according to the invention was obtained.
  • the thus-available graft copolymer PC1 had a K value of 38.4.
  • the proportion by weight of the copolymerized monomers was ethylene oxide: N-vinylpyrrolidone: N-vinylimidazole about 20:40:40.
  • the K value was determined according to H. Fikentscher, Cellulose-Chemie Vol. 13, pp. 58-64 and 71-74 (1932) at 25 ° C. in 1% by weight aqueous solution.

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

Abstract

L'invention concerne un procédé pour teindre un textile avec un ou plusieurs colorants de cuve. Ce procédé se caractérise en ce qu'il consiste à traiter un textile non teint avec un bain aqueux, contenant (a) au moins un colorant de cuve, (b) au moins un agent de réduction ou (a') au moins un colorant de cuve sous forme réduite et (c) au moins un composé de formule générale (Ia) ou (Ib), dans laquelle les variables sont définies comme suit : R1 est sélectionné parmi hydrogène, phényle, CH(CH3)C6H5 et alkyle en C1-C10 ; R2 est identique ou différent et sélectionné parmi hydrogène, phényle et alkyle en C1-C10 ; AO désigne oxyde d'alkylène ; EO désigne oxyde d'éthylène ; a est identique ou différent et sélectionné parmi des nombres de 0 à 150 ; b est identique ou différent et sélectionné parmi des nombres de 15 à 250, b étant = a ; d est identique ou différent et sélectionné parmi zéro et un ; M est identique ou différent et sélectionné parmi des métaux alcalins.
EP06725204A 2005-03-22 2006-03-21 Procede pour teindre des textiles avec un colorant de cuve Withdrawn EP1863972A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200510013781 DE102005013781A1 (de) 2005-03-22 2005-03-22 Verfahren zum Färben von Textilien mit Küpenfarbstoff
PCT/EP2006/060918 WO2006100244A2 (fr) 2005-03-22 2006-03-21 Procede pour teindre des textiles avec un colorant de cuve

Publications (1)

Publication Number Publication Date
EP1863972A2 true EP1863972A2 (fr) 2007-12-12

Family

ID=36954978

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06725204A Withdrawn EP1863972A2 (fr) 2005-03-22 2006-03-21 Procede pour teindre des textiles avec un colorant de cuve

Country Status (4)

Country Link
EP (1) EP1863972A2 (fr)
CN (1) CN101146953A (fr)
DE (1) DE102005013781A1 (fr)
WO (1) WO2006100244A2 (fr)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1121814B (de) * 1956-11-03 1962-01-11 Bayer Ag Verfahren zur Herstellung von Polyglykolaethern
DE2745449C2 (de) * 1977-10-08 1979-10-25 Basf Ag, 6700 Ludwigshafen Stabile feindisperse wäßrige Zubereitungen von Dispersionsfarbstoffen und optischen Aufhellern und deren Verwendung
DK0382138T3 (da) * 1989-02-08 1994-09-19 Ciba Geigy Ag Hjælpemiddelblanding og dens anvendelse ved farvning af syntetiske fibermaterialer
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

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2006100244A3 *

Also Published As

Publication number Publication date
WO2006100244A2 (fr) 2006-09-28
WO2006100244A3 (fr) 2007-01-11
CN101146953A (zh) 2008-03-19
DE102005013781A1 (de) 2006-09-28

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