EP0641402A1 - Teinture en continu de materiaux textiles cellulosiques. - Google Patents

Teinture en continu de materiaux textiles cellulosiques.

Info

Publication number
EP0641402A1
EP0641402A1 EP93909960A EP93909960A EP0641402A1 EP 0641402 A1 EP0641402 A1 EP 0641402A1 EP 93909960 A EP93909960 A EP 93909960A EP 93909960 A EP93909960 A EP 93909960A EP 0641402 A1 EP0641402 A1 EP 0641402A1
Authority
EP
European Patent Office
Prior art keywords
ether
textile materials
dyes
condensation products
treated
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
EP93909960A
Other languages
German (de)
English (en)
Other versions
EP0641402B1 (fr
Inventor
Joerg Schulze
Harald Schlueter
Kurt Bacher
Wolfgang Schrott
Erich Kromm
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 EP0641402A1 publication Critical patent/EP0641402A1/fr
Application granted granted Critical
Publication of EP0641402B1 publication Critical patent/EP0641402B1/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
    • 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
    • D06P1/667—Organo-phosphorus compounds
    • 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
    • D06P1/64—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 without sulfate or sulfonate groups
    • D06P1/651—Compounds without nitrogen
    • 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
    • D06P1/64—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 without sulfate or sulfonate groups
    • D06P1/651—Compounds without nitrogen
    • D06P1/65106—Oxygen-containing compounds
    • D06P1/65125—Compounds containing ester groups
    • 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
    • D06P1/655—Compounds containing ammonium groups
    • D06P1/66—Compounds containing ammonium groups containing quaternary ammonium groups
    • 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
    • D06P3/58—Material containing hydroxyl groups
    • D06P3/60—Natural or regenerated cellulose
    • D06P3/66—Natural or regenerated cellulose using reactive 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
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/22—Effecting variation of dye affinity on textile material by chemical means that react with the fibre
    • 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
    • Y10S8/93—Pretreatment before dyeing

Definitions

  • the invention relates to a process for the continuous production of surface dyeings on cellulose fibers which are in the form of textile materials, by treating the textile materials with an aqueous liquor which contains cationic polyquaternary condensation products and phosphoric acid esters, and subsequently dyeing the textile materials with reactive dyes and finishing the dyeings in the usual way.
  • Quaternized condensation products are known from US Pat. No. 5,015,754 which are obtained by reacting precondensates of trialkanolamines with carboxylic acid derivatives or epichiorhydrin and subsequent quaternization with benzyl chloride are true. These condensation products are used for the aftertreatment for the fixation of dyeings and prints on textile materials containing cellulose fibers.
  • the object of the present invention is to provide a method for the continuous production of surface dyeings on cellulose fibers which are in the form of textile materials. The object is achieved according to the invention if the textile materials are first treated with an aqueous liquor which
  • the cellulose fibers of the textile materials dyed in this way are not dyed throughout, but only on the upper surface. In such cases one also speaks of ring colorations. However, the textile material is colored no matter what. Textile materials which can be dyed by the process according to the invention are, for example, yarns, woven fabrics, knitted fabrics or nonwovens which consist of cellulose fibers or, if appropriate, contain them in a mixture with other fibers. Warp yarns made from cellulose fibers are preferably dyed by the process according to the invention.
  • the textile materials are first treated with an aqueous liquor which contains at least 5 g / l of condensation products quaternized with benzyl halides from precondensates of trialkanolamines and ureas, cyclic carbonates and / or epihalohydrins.
  • Quaternized condensation products of this type are described in detail in US-A-5 015 754.
  • the quaternized condensation products consist of A) a precondensate of one or more trialkanolamines of the general formula I.
  • radicals R 1 to R 3 represent 1,2-alkylene groups having 2 to 4 carbon atoms
  • n 0 or 1
  • R 8 is hydrogen, a C 1 -C 25 alkyl group, a
  • Chlorine or bromine means d) a monofunctional compound of the general formula Ild
  • R 9 is a C 1 -C 25 alkyl group, a C 2 -C 25 alkenyl group or a phenyl radical which
  • R 10 is an alkylene group with 1 to 50 C atoms which can be interrupted by one or more non-adjacent oxygen atoms and / or can contain one or more non-vicinal hydroxyl groups, and Z 1 , Z 2 chlorine, bromine, isocyanate or one of the groups or or OR 9
  • R 11 represents a C 1 -C 4 alkyl group, a C 1 -C 4 alkoxy group, fluorine, chlorine or bromine.
  • the precondensates used to prepare the cationic resins can be obtained by heating the trialkanolamines I, in particular triethanolamine or triisopropanolamine
  • N [CH 2 -CH (CH 3 ) -OH] 3 in the presence of acidic catalysts, preferably phosphorous or hypophosphorous acid, at temperatures of 120 to 280 ° C, as described in EP-A 223 064, can be obtained.
  • acidic catalysts preferably phosphorous or hypophosphorous acid
  • the reaction is expedient after reaching a viscosity range of 5,000 to 35,000 mPa ⁇ s, preferably from 10,000 to 25,000 mPa ⁇ s, for triethanolamine or from 100,000 to 600,000 mPa ⁇ s, preferably from 200,000 to 500,000 mPa.s.
  • ⁇ S for triisopropanolamine or from 100,000 to 250,000 mPa ⁇ s for a mixed condensate from preferably equimolar amounts of triethanolamine and triisopropanolamine (each measured in the undiluted state at 20 ° C.), broken off significantly below the gel point by cooling.
  • the precondensates obtained are reacted with one or more compounds Ha to Ile.
  • the amount of this Compounds is in the range from 1 to 30 mol%, preferably from 1 to 15 mol%, per mole of I.
  • Suitable compounds IIa to Ile are: a) the defined carboxylic acids or their derivatives Ha, where the radicals R 4 and R 5 are hydroxyl groups, C 1 -C 8 alkoxy groups, preferably C 1 -C 4 alkoxy groups, chlorine or bromine and for the bridge member R 6 in particular the groups and
  • urea N-methylurea, N-ethylurea, N-propylurea, N-butylurea, N, N'-dimethylurea, N, N'-diethylurea, N, N ' -Dipropylurea, N, N'-dibutylurea, N- (2-ethylhexyl) urea, N-iso-nonylurea, N-iso-tridecylurea, N-laurylurea, N-myristylurea, N-palmitylurea, N-stearylurea, N- , N-linolylurea, N-linolylurea, N-linolenylurea and N-phenylurea.
  • R 10 come in particular the groups and
  • q taking values from 1 to 50, preferably 2 to 10 and k taking values from 0 to 24, preferably 0 to 12, and R 12 being hydrogen, methyl or ethyl; unbranched bridge members R 10 are also preferred.
  • R 12 being hydrogen, methyl or ethyl; unbranched bridge members R 10 are also preferred.
  • the following are examples of compounds Ile: ⁇ ) dichlorides or dibromides, for example methylene chloride,
  • Hexane-1,6-diol-bis-glycidyl ether diethylene glycol bis-glycidyl ether, di [3- (glycidyloxy) propyl] ether, triethylene glycol bis-glycidyl ether, ethylene glycol bis [3-glycidyloxy) propyl] ether, tetraethylene glycol bis- glycidyl ether, pentaethylene glycol bis-glycidyl ether, hexaethylene glycol bis-glycidyl ether and neopentylene glycol bis-glycidyl ether; ⁇ ) ⁇ -alkoxy or ⁇ -aryloxypropylene halohydrides, e.g.
  • the quaternary condensation products described above as preferred are also preferably used in the first treatment bath in the dyeing process according to the invention.
  • Condensation products of piperazine and epichlorohydrin quaternized with benzyl chloride are also suitable. Condensation products of this type are, for example, from "The latest advances in the use of dyes” (Volume 2, page 96f) by L. Diserens, [2. Edition, published by Birk Reifen Basel 1949].
  • Piperazine and epichlorohydrin are condensed in a molar ratio (0.5-1): (1-0.5), preferably in a molar ratio of 1: 1.
  • the condensation product is then quaternized by reaction with benzyl chloride.
  • the quaternized condensation products in the form of a 50% aqueous solution have viscosities of 100 to 1000 Pa ⁇ s, preferably 200 to 500 mPa ⁇ s (measured at 20 ° C).
  • the concentration of the quaternized condensation products in the aqueous liquor is at least 5 g / l. Mixtures of the various condensation products can also be used. The concentration of quaternized condensation products can be up to 100 g / l or even more gene and is preferably in the range of 15 to 50 g / l. The quaternized condensation products are soluble in the aqueous liquor.
  • the temperature of the aqueous liquor into which the textile materials are introduced for treatment can be varied within a wide range. Temperatures of 15 to 95 ° C are suitable. The preferred treatment temperatures are 20 to 35 ° C.
  • aqueous liquor as component (ii) 0.02 to 1 g / l of a phosphoric acid triester, the alcohol component of which is derived from aliphatic, aryl-substituted aliphatic alcohols, phenols or alkyl-substituted phenols each having 6 to 18 carbon atoms in the alcohol or phenol radical.
  • Suitable phosphoric acid triesters are, for example, triisobutyl phosphate, tri (2-ethylhexyl) phosphate, trihexyl phosphate, tridecyl phosphate, tridodecyl phosphate, tri-tert-butylphenyl phosphate, tridodecylphenyl phosphate and mixtures of at least 2 of the phosphates mentioned.
  • the surface or ring dyeing of the cellulose fibers is carried out continuously by first passing textile materials containing or consisting of cellulose fibers, for example on an indigo dyeing machine, through a bath which contains the compounds (i) and (ii) in the amounts specified above contains.
  • the textile materials are preferably in the form of a yarn which, after treatment with the aqueous liquor described above, is squeezed out and passed into another bath and dyed therein with reactive dyes in an aqueous medium.
  • Suitable reactive groups are, for example, vinylsulfone, beta-sulfatoethylsulfone, beta-chloroethylsulfone and beta-dialkylaminoethylsulfone groups or heterocycles substituted by 1 to 3 halogen atoms, such as triazine, pyrdazine, pyridazone, quinoxaline and pyrimidine.
  • the reactive dyes can be one or contain several reactive groups.
  • the chromophoric part is primarily derived from azo compounds, disazo compounds, metal complexes of azo dyes or disazo dyes, anthraquinone derivatives, formazans and
  • the cellulose fibers are dyed with reactive dyes by known methods, e.g. in the temperature range from 20 to 95 ° C.
  • the textile material coming from the dyebath is then continuously treated with an alkaline liquor to fix the reactive dyes, through which it is passed continuously.
  • the staining is also fixed and completed in a conventional manner.
  • the textile material is preferably passed through an aqueous liquor which contains 0.5 to 2 g / l of a washing and / or dispersing agent. The material is then rinsed once or several times with water.
  • Cationic Compound I Aqueous solution of a polyquaternary compound which was obtained according to synthesis example 5 of US-A-5 015 754 by condensation of a triethanolamine precondensate with 5 mol% urea and subsequent quaternization with 90 mol% benzyl chloride.
  • Phosphoric acid ester I Neutral phosphoric acid triester of an aliphatic alcohol with 8 carbon atoms.
  • Example 1 A raw cotton yarn (12 Nm / l) is passed for 10 seconds through a liquor which contains 4 parts of the cationic compound I, 0.03 parts of the phosphoric acid ester I.
  • the cotton yarn is squeezed to about 40% liquor absorption and passed through an air passage for one minute.
  • the second liquor trough through which the yarn is again immersed wet for 10 seconds, contains 3 parts of the reactive dye CI Reactive Blue 21 and 3 parts of NaCl.
  • the liquor addition after padding was approximately 25%.
  • a one-minute airflow followed.
  • the dye was fixed with an alkaline solution at 95 ° C.
  • the fixing liquor contained 15 parts by volume of NaOH 38 ° Be and 20 parts of NaCl.
  • a turquoise-colored yarn is obtained in which the cellulose fibers have a very good ring color, which is essential for the denim article with wash-down effects.
  • the fastness properties achieved correspond to those which are usually obtained for a denim article with wash-down effects.
  • a raw cotton yarn (12 Nm / l) is passed through a liquor containing 4 parts of the cationic compound I, 0.03 part of the phosphoric acid ester I and 0.05 part of a commercially available nonionic wetting agent for 10 seconds.
  • the cotton yarn is squeezed to about 40% liquor absorption and passed through an air passage for one minute.
  • the second liquor trough through which the yarn is again immersed wet for 10 seconds, contains 3 parts of the reactive dye C.I. Reactive Blue 21 and 3 parts NaCl.
  • the liquor addition after padding was approximately 25%.
  • a one-minute airflow followed.
  • the dye was fixed with an alkaline solution at 95 ° C.
  • the fixing liquor contained 15 parts by volume of NaOH 38 ° Be and 20 parts of NaCl.
  • a raw cotton yarn (12 Nm / 1) is passed for 10 seconds through a liquor which contains 4 parts of the cationic compounds II and 0.03 parts of the phosphoric acid ester I.
  • the cotton yarn is squeezed to about 40% liquor absorption and passed through an air passage for one minute.
  • the second liquor trough through which the yarn is dipped wet in wet again for 10 seconds, contains 3 parts of the reactive dye C.I. Reactive Red 24 and 3 parts NaCl.
  • the liquor addition after fouarding was approx. 25%.
  • a one-minute airflow followed.
  • the dye was fixed with an alkaline solution at 95 ° C.
  • the fixing liquor contained 15 volumes of NaOH 38 ° Be and
  • Warp yarns The yarn was then rinsed again and then dried.
  • a red yarn is obtained.
  • the individual cellulose fibers have a very good ring color.
  • the fastness properties obtained correspond to those which are customary for a denim article with wash-down effects.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP93909960A 1992-05-20 1993-05-12 Teinture en continu de materiaux textiles cellulosiques Expired - Lifetime EP0641402B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4216591A DE4216591A1 (de) 1992-05-20 1992-05-20 Verfahren zur kontinuierlichen Erzeugung von Oberflächenfärbungen auf Cellulosefasern, die in Form textiler Materialien vorliegen
DE4216591 1992-05-20
PCT/EP1993/001172 WO1993023605A1 (fr) 1992-05-20 1993-05-12 Teinture en continu de materiaux textiles cellulosiques

Publications (2)

Publication Number Publication Date
EP0641402A1 true EP0641402A1 (fr) 1995-03-08
EP0641402B1 EP0641402B1 (fr) 1996-09-11

Family

ID=6459279

Family Applications (1)

Application Number Title Priority Date Filing Date
EP93909960A Expired - Lifetime EP0641402B1 (fr) 1992-05-20 1993-05-12 Teinture en continu de materiaux textiles cellulosiques

Country Status (10)

Country Link
US (1) US5484457A (fr)
EP (1) EP0641402B1 (fr)
JP (1) JPH07506633A (fr)
KR (1) KR100248166B1 (fr)
AT (1) ATE142721T1 (fr)
BR (1) BR9306390A (fr)
DE (2) DE4216591A1 (fr)
ES (1) ES2093424T3 (fr)
TR (1) TR26961A (fr)
WO (1) WO1993023605A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5667533A (en) * 1996-02-07 1997-09-16 The Virkler Company Heather dyed fabric and method of producing same
US6905524B2 (en) * 2001-11-09 2005-06-14 Polymer Group, Inc. Method of continuously dyeing nonwoven fabrics and the products thereof
DE102004045861B4 (de) * 2004-09-20 2008-05-08 Dystar Textilfarben Gmbh & Co. Deutschland Kg Verfahren zur Ringfärbung von textilen Flächengebilden aus cellulosischen Fasern und Mischmaterialien enthaltend cellulosische Fasern und danach hergestellte ringgefärbte Gewebe und Mischmaterialien

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE713902C (de) * 1938-07-14 1941-11-22 I G Farbenindustrie Akt Ges Verfahren zum Drucken von Textilstoffen
US3233961A (en) * 1963-05-15 1966-02-08 Celanese Corp Process for dyeing cellulose acetate having an acetyl value of at least 59% in the presence of hydroxyalkylamine-fatty acid condensation products
FR2509302A1 (fr) * 1981-03-04 1983-01-14 Vyzk Ustav Zuslechtovaci Composes d'ammonium quaternaire, procede pour leur fabrication et utilisation de ces produits dans les apprets de finissage des tissus
DE3320629A1 (de) * 1983-06-08 1984-12-13 Basf Ag, 6700 Ludwigshafen Verfahren zum faerben von textilen materialien aus hydrophilen fasern
FR2551474B1 (fr) * 1983-09-01 1986-12-05 Sandoz Sa Procede de traitement de matieres textiles cellulosiques
DE3829974A1 (de) * 1988-09-03 1990-03-15 Basf Ag Quaternierte kondensationsprodukte

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9323605A1 *

Also Published As

Publication number Publication date
EP0641402B1 (fr) 1996-09-11
DE4216591A1 (de) 1993-11-25
BR9306390A (pt) 1998-09-01
KR100248166B1 (ko) 2000-03-15
KR950701697A (ko) 1995-04-28
JPH07506633A (ja) 1995-07-20
DE59303770D1 (de) 1996-10-17
WO1993023605A1 (fr) 1993-11-25
US5484457A (en) 1996-01-16
ES2093424T3 (es) 1996-12-16
TR26961A (tr) 1994-09-12
ATE142721T1 (de) 1996-09-15

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