EP0359188A2 - Procédé de teinture et d'impression de fibres cellulosiques en absence d'alcali ou d'agents réducteurs - Google Patents

Procédé de teinture et d'impression de fibres cellulosiques en absence d'alcali ou d'agents réducteurs Download PDF

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Publication number
EP0359188A2
EP0359188A2 EP89116832A EP89116832A EP0359188A2 EP 0359188 A2 EP0359188 A2 EP 0359188A2 EP 89116832 A EP89116832 A EP 89116832A EP 89116832 A EP89116832 A EP 89116832A EP 0359188 A2 EP0359188 A2 EP 0359188A2
Authority
EP
European Patent Office
Prior art keywords
dyes
dyeing
alkali
carbon atoms
formula
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
EP89116832A
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German (de)
English (en)
Other versions
EP0359188B1 (fr
EP0359188A3 (en
Inventor
Klaus Sternberger
Karl-Heinz Dr. Keil
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.)
Hoechst AG
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Hoechst AG
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Publication date
Application filed by Hoechst AG filed Critical Hoechst AG
Priority to AT89116832T priority Critical patent/ATE98710T1/de
Publication of EP0359188A2 publication Critical patent/EP0359188A2/fr
Publication of EP0359188A3 publication Critical patent/EP0359188A3/de
Application granted granted Critical
Publication of EP0359188B1 publication Critical patent/EP0359188B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/44General 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
    • D06P1/64General 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
    • D06P1/642Compounds containing nitrogen
    • D06P1/645Aliphatic, araliphatic or cycloaliphatic compounds containing amino groups
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58Material containing hydroxyl groups
    • D06P3/60Natural or regenerated cellulose
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916Natural fiber dyeing
    • Y10S8/918Cellulose textile

Definitions

  • the dyeing of textile materials can be carried out according to known methods in that the textile material is drawn out with a dyeing liquor containing reactive dye, usually at elevated temperature and with most commercially available reactive dye types in the presence of alkali, or continuous or discontinuous processes, such as the so-called pad-steam process, or the cold retention process can be used.
  • a dyeing liquor containing reactive dye usually at elevated temperature and with most commercially available reactive dye types in the presence of alkali, or continuous or discontinuous processes, such as the so-called pad-steam process, or the cold retention process can be used.
  • the textile material is first padded with a reactive dye liquor, the alkali required for fixation being usually applied in a separate impregnation step.
  • the dye fixation is then carried out by a steaming process, in the cold dwell process by docking the impregnated goods and lingering for several hours at room temperature.
  • Other fixation options such as The treatment of the goods, which have been sealed with an alkali-free reactive dye liquor, using sodium hydroxide solution / water glass solution has become known and is practiced industrially.
  • U.S. Patent 4,806,126 is a process for dyeing cellulosic fibers with reactive dyes described in which the presence of alkali is not required.
  • the fixation of the dyes on the fibers is achieved in this process in that the fibers are pretreated with a reaction product of polyethylene amine and a bifunctional alkylating agent before dyeing.
  • the auxiliary required for the pretreatment is known from US-A 3 544 363.
  • the tool is used there exclusively for the improvement of the wet fastness properties of dyeings with sulfur dyes. Pretreatment with this aid and subsequent dyeing without alkali is not described there.
  • the pretreatment agents to be used according to the invention are prepared by reacting an epihalohydrin, preferably epichlorohydrin, with ammonia or an amine of the formula given at temperatures of about 60 to 70 ° C. in water or a lower alcohol as solvent.
  • These pretreatment agents can optionally be quaternized with C1-C4, preferably C1-C3 alkyl groups.
  • the quaternization can be carried out using alkyl halides, preferably alkyl chlorides, or dialkyl sulfonates by known methods.
  • amines which correspond to the formula given above are: monomethyl, ethyl, propyl, isopropyl, butyl, isobutylamine, monooxethyl, monooxypropylamine, ethylenediamine, diaminopropanes, diaminobutanes, diaminohexanes, 3 , 3'-diaminodipropyl ether, piperazine, monooxethyl and di-oxuschuschusch/vonäthendiamamin, diethylenetriamine, dipropylenetriamine, triethylenetetramine and. a.
  • This aid described above is applied to the textile material to be dyed or printed together with a wetting or padding aid from an aqueous liquor which is customary in the textile industry.
  • Raw or pre-treated cotton or mixed fabrics containing cotton are possible as textile materials.
  • the process according to the invention is particularly interesting for the pretreatment of cotton warp yarns with the aid described in the size. After weaving with untreated weft yarns and the subsequent alkali-free over-dyeing with reactive dyes, a denim effect is then achieved after washing out the fabric.
  • the pretreatment with the auxiliary together with a nonionic wetting agent is carried out from an aqueous liquor by customary methods by padding or in the exhaust process at temperatures of approximately 20 to 70 ° C., preferably 40 to 60 ° C., in the size from 80 ° C. to cooking temperature.
  • the liquor is adjusted to a weakly acidic pH, preferably pH 6.
  • the amount of auxiliary is about 3 to 10%, preferably 3 to 8%, based on the weight of the goods.
  • the amount of wetting agent is preferably 2 to 4 g / l.
  • the pretreatment liquor is then squeezed off and the goods are dried.
  • the goods pretreated in this way are then dyed with reactive dyes using customary methods and on customary dyeing units, for example using the cold dwelling method, the exhaust method or the heat setting method.
  • the fleet ratio can be about 1: 3 to 1:40.
  • Suitable reactive dyes in this process are all known types of reactive dyes which contain groups which are reactive with the hydroxyl groups of cellulose and which, under the dyeing conditions described according to the invention, preferably react by reaction with the polymers described and fixed on the cellulose material.
  • the reactive groups are, for example, groups with easily removable substituents which leave an electrophilic residue, such as reactive groups of the vinylsulfone type, groups of the ring systems quinoxaline, phthalazine, triazine, pyrimidine or pyridazone substituted with halogen atoms or reactive groups substituted with alkylsulfonyl groups in the case of sulfonylpyrimidothiazole or sulfonylbenzylbenzene .
  • groups with easily removable substituents which leave an electrophilic residue such as reactive groups of the vinylsulfone type, groups of the ring systems quinoxaline, phthalazine, triazine, pyrimidine or pyridazone substituted with halogen atoms or reactive groups substituted with alkylsulfonyl groups in the case of sulfonylpyrimidothiazole or sulfonylbenzylbenzene .
  • dyes with the reactive groups ß-sulfatoethylsulfone, ß-thiosulfatoethylsulfone, ß-phosphatoethylsulfone, chlorotriazinylamino, trichloropyrimidylamino, dichloropyrimidylamino, dichloro-pyrid amino, 2-methylsulfonyl-benzothiazol-6-yl-amino, 2,3-dichloroquinoxalin-6-yl-carbonylamino or 4-chloro-5-methyl-2-methylsulfonylpyrimid-3-yl-amino.
  • Suitable basic dye bodies of the reactive dyes are, for example, water-soluble azo, disazo, formazan, anthraquinone, dioxazine or phthalocyanine dyes.
  • Water-soluble azo and disazo reactive dyes which can also be metal complex reactive dyes, are preferably used. After dyeing, the goods are finished by rinsing, possibly soaping and drying.
  • the process according to the invention can be carried out not only with reactive dyes, but also in the same way with other types of dyes which contain anionic, for example sulfo groups, such as, for example, direct dyes, acid dyes and water-soluble sulfur dyes. Similar effects and fastness properties are achieved with these dyes as with the reactive dyes.
  • sulfur vat dyes can also be used in the process.
  • the method according to the invention is not only suitable for dyeing textile material, but also for printing.
  • the textile material is printed with a printing paste which contains a marking dye and the auxiliary agent to be used according to the invention.
  • the textile material is then over-dyed with reactive dyes without alkali, preferably using the pad-steam process or the pull-out process.
  • the cotton chains or cotton fabrics preheated with the aid described are printed with a printing paste which contains the reactive dye but no alkali and then the dyeing, for. B. fixed by steaming at 102-105 ° C for 8 minutes.
  • the subsequent post-treatment is carried out analogously to the dyeings.
  • the main advantage of the process according to the invention is that, as a result of the pretreatment with the auxiliary described, no alkali or reducing agent is required in the subsequent dyeing. When the goods are finally washed out after dyeing, no alkali then goes into the wastewater, so that the salt pollution of the wastewater in the dyeing plants is significantly reduced.
  • the pretreatment described also partially results in a significant deepening of the color in comparison to a coloration with the same amount of reactive dye in one conventional dyeing process.
  • water glass is used to a large extent as the alkali for fixing the reactive dyes. If this water glass is not carefully washed out after fixing, it can lead to annoying SiO2 deposits on the goods and thus impair the grip.
  • This disadvantage is also eliminated in the method according to the invention.
  • This new process also makes washing out the unfixed dye residues easier by dispensing with alkali, since in the presence of alkali the cotton fiber swells and the unfixed dye is more strongly absorbed. This does not apply to the method according to the invention.
  • the solubility of the reactive dyes, which is severely restricted by the alkali, is significantly improved and the stability of the neutral dye liquors is increased.
  • the dyeings produced by the process according to the invention described above show good wet fastness properties, but especially in the case of denim effects and individual dyestuffs, there is in part a slight discoloration of the undyed weft thread and, above all, a cloudy shade.
  • the amount of alkali perborate in the detergents is between about 4 and 25% by weight.
  • Such detergents containing perborate, which are suitable here, are described in detail in "Tenside" 18, p. 246 (1981).
  • cotton warp yarns are treated with a fleet of the following composition in the trough provided: 30 g / l polyvinyl alcohol (PVA) 5 g / l polyethylene glycol 4 g / l di-2-ethylhexyl phosphate potassium salt 60 g / l reaction product from NH3 and epichlorohydrin according to DE 1 619 391, Example 1.
  • the fleet intake is 100-120% (high-performance crushing unit).
  • the yarn runs at a speed of 15 m / sec, the liquor temperature is 80 - 90 ° C.
  • the cotton chains After leaving the sizing trough, the cotton chains are dried with contact heat at approx. 130 ° C.
  • PVA starch
  • modified starch or mixtures of these products can also be used.
  • the cotton chains are then woven with the weft cotton yarn and the fabric obtained is padded with a solution having the following composition on a cold residence unit consisting of dyeing pad and docking device: 10 g / l CJ Reactive Blue 19 (CI No. 61200) 4g / l wetting agent (4-nonylphenol polyglycol ether).
  • the goods padded in this way are wrapped in an airtight manner on a dock with a polyethylene film and left to rotate for a maximum of 24 hours.
  • a bleached cotton fabric is placed on a 2 or 3-roll pad with a solution 60 g / l of the reaction product according to DE 1 619 391, example 1 and 2 g / l di-2-ethylhexyl phosphate potassium salt contains, padded and after drying padded with a liquor which 10 g / l reactive red (CI No. 18158) and 2 g / l wetting agent (4-nonylphenol polyglycol ether) contains.
  • the dyeing is lingered and treated according to Example 1 of this application.
  • a deep red color is obtained with good fastness properties.
  • the corresponding cold dyed dye which was stained with the normal amount of alkali (NaOH / water glass), on the other hand, shows only a light pink shade.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
EP89116832A 1988-09-16 1989-09-12 Procédé de teinture et d'impression de fibres cellulosiques en absence d'alcali ou d'agents réducteurs Expired - Lifetime EP0359188B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT89116832T ATE98710T1 (de) 1988-09-16 1989-09-12 Verfahren zum faerben und bedrucken von cellulosefasern in abwesenheit von alkali oder reduktionsmitteln.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3831464A DE3831464A1 (de) 1988-09-16 1988-09-16 Verfahren zum alkali-freien faerben und bedrucken von cellulosefasern
DE3831464 1988-09-16

Publications (3)

Publication Number Publication Date
EP0359188A2 true EP0359188A2 (fr) 1990-03-21
EP0359188A3 EP0359188A3 (en) 1990-10-24
EP0359188B1 EP0359188B1 (fr) 1993-12-15

Family

ID=6363050

Family Applications (1)

Application Number Title Priority Date Filing Date
EP89116832A Expired - Lifetime EP0359188B1 (fr) 1988-09-16 1989-09-12 Procédé de teinture et d'impression de fibres cellulosiques en absence d'alcali ou d'agents réducteurs

Country Status (13)

Country Link
US (1) US4988365A (fr)
EP (1) EP0359188B1 (fr)
JP (1) JPH02112488A (fr)
KR (1) KR970007924B1 (fr)
AT (1) ATE98710T1 (fr)
AU (1) AU617866B2 (fr)
BR (1) BR8904657A (fr)
DE (2) DE3831464A1 (fr)
ES (1) ES2048249T3 (fr)
PH (1) PH26449A (fr)
PT (1) PT91700B (fr)
TR (1) TR24099A (fr)
ZA (1) ZA897047B (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0402879A1 (fr) * 1989-06-16 1990-12-19 Hoechst Aktiengesellschaft Procédé pour obtenir des effets de motif par coloration ou impression de matériau textile ou l'absence d'alcali ou d'agent réducteur
EP0665311A1 (fr) * 1994-01-29 1995-08-02 Hoechst Aktiengesellschaft Fibres synthétiques cellulosiques aminées
EP0692559A1 (fr) 1994-06-30 1996-01-17 Hoechst Aktiengesellschaft Fibres synthétiques cellulosiques modifiées par des composés aminés polymères
EP0692558A1 (fr) 1994-06-30 1996-01-17 Hoechst Aktiengesellschaft Procédé pour la fabrication de fibres aminées de cellulose régénerée
US5565007A (en) * 1994-05-17 1996-10-15 Hoechst Aktiengesellschaft Amination of rayon
CN111395013A (zh) * 2020-06-02 2020-07-10 佛山市南海区今易德纺织有限公司 一种牛仔面料的快速染色工艺

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW201803B (fr) * 1991-04-15 1993-03-11 Hoechst Ag
TW211595B (fr) * 1991-12-07 1993-08-21 Hoechst Ag
US5378242A (en) * 1992-12-22 1995-01-03 Apollo Chemical Company Liquid alkali for soaping off reactive dyes
DE4306432A1 (de) * 1993-03-02 1994-09-08 Hoechst Ag Verfahren zum Bedrucken und Färben von Textilien (Inverser Reservedruck)
DE4325783A1 (de) * 1993-07-31 1995-02-02 Hoechst Ag Verfahren zum Modifizieren und Färben von modifizierten Fasermaterialien
US20110009021A1 (en) * 2009-04-16 2011-01-13 Schoots Harrie P Colorfastness and finishing compounds
WO2012127274A1 (fr) * 2011-03-18 2012-09-27 Indian Institute Of Technology Delhi Appareil et procédés permettant de teindre des fibres
CN104452332A (zh) * 2014-12-05 2015-03-25 江苏太子鳄服饰有限公司 用于印染牛仔布的方法
US10737008B2 (en) 2015-08-17 2020-08-11 Abiomed, Inc. Dual lumen sheath for arterial access
CN106087464B (zh) * 2016-07-22 2020-08-14 沈阳化工研究院有限公司 一种染色、印花工艺
CN111549546B (zh) * 2020-06-01 2023-02-03 安徽中天纺织科技股份有限公司 一种锦棉混纺织物深色连续染色方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3544363A (en) * 1965-11-09 1970-12-01 Cassella Farbwerke Mainkur Ag Dyed textile materials having improved wet fastness properties and method of producing same
EP0146955A2 (fr) * 1983-12-22 1985-07-03 CASSELLA Aktiengesellschaft Procédé d'encollage et de teinture simultanés pour des teintures à solidités améliorées
EP0284010A2 (fr) * 1987-03-25 1988-09-28 Hoechst Aktiengesellschaft Procédé de teinture et impression sans alcali

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3329029A1 (de) * 1983-08-11 1985-02-28 Cassella Ag, 6000 Frankfurt Verfahren zur herstellung von faerbungen mit reaktivfarbstoffen

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3544363A (en) * 1965-11-09 1970-12-01 Cassella Farbwerke Mainkur Ag Dyed textile materials having improved wet fastness properties and method of producing same
EP0146955A2 (fr) * 1983-12-22 1985-07-03 CASSELLA Aktiengesellschaft Procédé d'encollage et de teinture simultanés pour des teintures à solidités améliorées
EP0284010A2 (fr) * 1987-03-25 1988-09-28 Hoechst Aktiengesellschaft Procédé de teinture et impression sans alcali

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0402879A1 (fr) * 1989-06-16 1990-12-19 Hoechst Aktiengesellschaft Procédé pour obtenir des effets de motif par coloration ou impression de matériau textile ou l'absence d'alcali ou d'agent réducteur
EP0665311A1 (fr) * 1994-01-29 1995-08-02 Hoechst Aktiengesellschaft Fibres synthétiques cellulosiques aminées
US5684141A (en) * 1994-01-29 1997-11-04 Hoechst Aktiengesellschaft Aminated cellulosic synthetic fibers
US5865858A (en) * 1994-01-29 1999-02-02 Hoechst Aktiengesellschaft Aminated cellulosic synthetic fibers
US5565007A (en) * 1994-05-17 1996-10-15 Hoechst Aktiengesellschaft Amination of rayon
EP0692559A1 (fr) 1994-06-30 1996-01-17 Hoechst Aktiengesellschaft Fibres synthétiques cellulosiques modifiées par des composés aminés polymères
EP0692558A1 (fr) 1994-06-30 1996-01-17 Hoechst Aktiengesellschaft Procédé pour la fabrication de fibres aminées de cellulose régénerée
US5529585A (en) * 1994-06-30 1996-06-25 Hoechst Ag Rayon modified with polymeric amine compounds
CN111395013A (zh) * 2020-06-02 2020-07-10 佛山市南海区今易德纺织有限公司 一种牛仔面料的快速染色工艺
CN111395013B (zh) * 2020-06-02 2020-10-27 佛山市南海区今易德纺织有限公司 一种牛仔面料的快速染色工艺

Also Published As

Publication number Publication date
KR900005013A (ko) 1990-04-13
ZA897047B (en) 1990-06-27
US4988365A (en) 1991-01-29
AU617866B2 (en) 1991-12-05
DE58906427D1 (de) 1994-01-27
AU4134789A (en) 1990-05-17
PT91700B (pt) 1995-05-31
KR970007924B1 (ko) 1997-05-17
PH26449A (en) 1992-07-15
ATE98710T1 (de) 1994-01-15
EP0359188B1 (fr) 1993-12-15
EP0359188A3 (en) 1990-10-24
JPH02112488A (ja) 1990-04-25
BR8904657A (pt) 1990-04-24
ES2048249T3 (es) 1994-03-16
DE3831464A1 (de) 1990-03-29
TR24099A (tr) 1991-03-18
PT91700A (pt) 1990-03-30

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