EP0225282B1 - Verfahren zur Nachbehandlung von gefärbtem Cellulosefasermaterial - Google Patents

Verfahren zur Nachbehandlung von gefärbtem Cellulosefasermaterial Download PDF

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Publication number
EP0225282B1
EP0225282B1 EP86810502A EP86810502A EP0225282B1 EP 0225282 B1 EP0225282 B1 EP 0225282B1 EP 86810502 A EP86810502 A EP 86810502A EP 86810502 A EP86810502 A EP 86810502A EP 0225282 B1 EP0225282 B1 EP 0225282B1
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EP
European Patent Office
Prior art keywords
process according
formula
carbon atoms
ammonium salt
lower alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP86810502A
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German (de)
English (en)
French (fr)
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EP0225282A1 (de
Inventor
Rosemarie Töpfl
Heinz Abel
Jörg Binz
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Novartis AG
Original Assignee
Ciba Geigy AG
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Publication date
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Publication of EP0225282A1 publication Critical patent/EP0225282A1/de
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/02—After-treatment
    • D06P5/04—After-treatment with organic compounds
    • D06P5/08—After-treatment with organic compounds macromolecular
    • 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
    • D06P5/02—After-treatment
    • D06P5/04—After-treatment with organic compounds
    • D06P5/06—After-treatment with organic compounds containing nitrogen

Definitions

  • the present invention relates to a method for the aftertreatment of colored cellulose fiber material, in particular cellulose-containing textile material.
  • Components (A) and (B) can be present as individual compounds or as mixtures with one another.
  • Lower alkyl and lower alkoxy in the definition of the radicals in formula (1) and in the formulas below represent those groups or group components which have 1 to 5 carbon atoms, e.g. Methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl or amyl or methoxy, ethoxy or isopropoxy.
  • the aliphatic radicals R 1 and R 2 can be straight-chain or branched. Together with the CO group, they advantageously represent the acid residue of an unsaturated or preferably saturated aliphatic carboxylic acid with 8 to 24 carbon atoms.
  • aliphatic carboxylic acids are 2-ethyl-hexanoic acid, capric, lauric, coconut fat, myristic, palm kernel fat , Palmitic, tallow fatty, oleic, ricinoleic, linoleic, linolenic, stearic, arachic, arachidonic, behenic, erucic or lignoceric acid.
  • Behenic acid is the preferred acid.
  • Mixtures of these acids can also be used.
  • Coconut fatty acid, palm kernel fatty acid, palmitic / stearic acid mixtures, tallow fatty acid and especially arachinic / behenic acid mixtures are particularly preferred mixtures.
  • R i and R 2 each preferably represent an alkyl radical having 7 to 23 carbon atoms and in particular having 19 to 21 carbon atoms.
  • the lower radicals R s to R 6 are preferably identical and are in particular methyl, ethyl, isopropyl or hydroxyethyl. Methyl is particularly preferred.
  • X i and X 2 are preferably -HN-.
  • Zi and Z 2 represent in particular an alkylene group which contains 2 to 5 carbon atoms and can be straight-chain or branched. These are, for example, the -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -, -CH 2 -CH 2 - and especially -CH 2 CH 2 CH 2 - are particularly preferred.
  • the aliphatic hydrocarbon chain in the bridge member Q preferably has 3 to 10 carbon atoms. It can be straight or branched.
  • Q is preferably an alkylene radical with 3 to 10 carbon atoms which is optionally interrupted in the chain by oxygen and optionally substituted by hydroxyl groups.
  • the alkylene radical is preferably substituted by hydroxyl.
  • Preferred bridge members Q are are particularly preferred.
  • Anions Y e include both anions of inorganic acids, such as, for example, the chloride, bromide, fluoride, iodide or sulfate ion, and also anions of organic acids, for example aromatic or aliphatic sulfonic acids, such as, for example, benzenesulfonate, p-toluenesulfonate, Chlorobenzenesulfonate, methane or ethanesulfonate ion, furthermore the anions of lower carboxylic acids, such as acetate, propionate or oxalate ion.
  • inorganic acids such as, for example, the chloride, bromide, fluoride, iodide or sulfate ion
  • organic acids for example aromatic or aliphatic sulfonic acids, such as, for example, benzenesulfonate, p-toluenesulfonate, Chlorobenzen
  • Y e is primarily the chloride, bromide, sulfate or p-toluenesulfonate ion.
  • the diquaternary ammonium salts of the formula (1) are prepared in a manner known per se.
  • the preparation can preferably be carried out by adding 1 mol of a compound of the formulas and or 2 moles of the same compound with 1 mole of a Q-introducing compound having two functional groups, such as, for example, epihalohydrin, dihaloalkanes, dihaloalkyl ethers, olefin dioxides, diepoxy compounds, such as ⁇ , w-alkanediol diglycidyl ether or alkanediol alkyl or aryl sulphonates.
  • a Q-introducing compound having two functional groups such as, for example, epihalohydrin, dihaloalkanes, dihaloalkyl ethers, olefin dioxides, diepoxy compounds, such as ⁇ , w-alkanediol diglycidyl ether or alkanediol alkyl or aryl sulphon
  • the reaction is preferably carried out in a polar solvent and, if necessary, with the addition of a hydrohalic acid such as e.g. Hydrochloric acid or sulfuric acid.
  • a hydrohalic acid such as e.g. Hydrochloric acid or sulfuric acid.
  • Suitable polar solvents are water or preferably water-miscible organic solvents.
  • water-miscible organic solvents are aliphatic C 1 -Cs alcohols, such as methanol, ethanol or the propanols; Alkylene glycols, such as ethylene glycol or propylene glycol; Monoalkyl ethers of glycols, such as, for example, ethylene glycol monomethyl, ethyl or butyl ether and diethylene glycol monomethyl or ethyl ether; Ketones such as acetone and diacetone alcohol; Ethers, such as diisopropyl ether, diphenyl oxide, dioxane, tetrahydrofuran, and also tetrahydrofurfuryl alcohol, acetonitrile, y-butyrolactone or N, N-dimethylformamide. Mixtures of the solvents mentioned can also be used.
  • the polybasic nitrogen-containing polycondensates (component (B) which can be used are (1) amino groups-containing condensates which have been prepared by reacting dicyandiamide, cyanamide, guanidine or bisguanidine and polyalkylene amines with at least three primary and / or secondary amino groups, the condensates containing an epihalohydrin can be further reacted and / or acidified
  • component (B) which can be used are (1) amino groups-containing condensates which have been prepared by reacting dicyandiamide, cyanamide, guanidine or bisguanidine and polyalkylene amines with at least three primary and / or secondary amino groups, the condensates containing an epihalohydrin can be further reacted and / or acidified
  • These condensates and the corresponding starting materials are known from DE-AS 1 595 390 and can be prepared by the process described therein.
  • Reaction products of polyalkylene polyamines with at least 3 amino groups and dicyandiamide or cyanodiamide are preferred. Reaction products from diethylenetriamine and dicyandiamide are particularly preferred. However, triethylenetetramine, tetraethylene pentamine, pentaethylene hexamine, dipropylenetriamine, N-bis (aminopropyl) methylamine and their mixtures or the polyamine mixtures obtained in the preparation of such polyamines can also be used as polyamines.
  • component (B) Other basic nitrogen-containing polycondensates suitable as component (B) are (2) reaction products of a peralkylated aliphatic di- or triamine with a dihaloalkyl ether e.g. ⁇ , ⁇ '-dibromo-diethyl ether or ⁇ , ⁇ '-dichlorodiethyl ether.
  • a dihaloalkyl ether e.g. ⁇ , ⁇ '-dibromo-diethyl ether or ⁇ , ⁇ '-dichlorodiethyl ether.
  • Such polyquaternary ammonium salts are e.g. described in DE-PS 894 237.
  • Components (A) and (B) are generally used in a weight ratio of 4: 1 to 1: 4, preferably 3: 1 to 1: 2.
  • Components (A) and (B) are usually added separately, simultaneously or in stages to the aftertreatment liquor. However, they can also be used in the form of an aqueous preparation. This preparation can be obtained by simply stirring the components in water, if necessary by heating to 50 to 70 ° C. and diluting with water to a 20 to 40% solution.
  • the aftertreatment according to the invention of the dyed cellulose-containing fiber material is as a rule carried out after dyeing, but preferably from a fresh bath.
  • Regenerated or in particular natural cellulose can be considered as fiber material, such as e.g. Cellulose, viscose silk, hemp, linen, jute or preferably cotton, as well as fiber blends with synthetic fibers e.g. those made of polyamide / cotton or in particular of polyester / cotton, where the polyester portion can be pre-colored with disperse dyes.
  • the textile is applicable in any form, such as. e.g. Yarns, skeins of yarn, woven fabrics, knitted fabrics, felts, preferably in the form of textile fabrics, such as woven fabrics, knitted fabrics or carpets, which consist entirely or partially of native, regenerated or modified cellulose.
  • the cellulose fiber material is usually dyed with reactive dyes or with substantive dyes. You can use the pull-out procedure or two-stage processes such as the padding process or printing are generated, the padding process or the pad-cold dwelling process being particularly suitable as padding process.
  • the amount of dyes used depends on the desired depth of color. In general, amounts of 0.1 to 10 percent by weight, in particular 0.5 to 5 percent by weight, based on the material used, have proven successful.
  • the usual direct dyes are suitable as noun dyes, for example the "Direct Dyes” mentioned in Color Index, 3rd edition (1971) Volume 2 on pages 2005-2478.
  • Reactive dyes are understood to be the usual dyes that form a chemical bond with the cellulose, e.g. the "Reactive Dyes” listed in Color Index, Volume 3 (3rd Edition, 1971) on pages 3391-3560 and Volume 6 (Revised 3rd Edition, 1975) on Pages 6268-6345.
  • the advantages of the method according to the invention come especially in the aftertreatment of Colorings with noun dyes to wear.
  • Azo dyes and anthraquinone dyes and especially polyazo dyes with 2 to 6 sulfonic acid groups are particularly suitable.
  • the aftertreatment according to the invention is preferably carried out using the exhaust process. However, it can equally well be carried out continuously by spraying on or, preferably, using the padding method.
  • the liquor ratio can be selected within a wide range, for example: 1: 3 to 1: 100, preferably 1:10 to 1:50. It is convenient to work at a temperature of 20 to 98 ° C, preferably 25 to 60 ° C in the exhaust process and 20 to 30 ° C in the padding process.
  • Special devices are not required in the method according to the invention.
  • the usual dyeing machines e.g. open baths, reel runners, jiggers, paddle, jet or circulation devices can be used.
  • the treatment liquors contain components (A) and (B) in the exhaust process, preferably each in an amount of 0.1 to 3% by weight, in particular 0.15 to 2% by weight or especially 0.15 to 0.6 %
  • By weight based on the weight of the cellulose material or in the case of padding liquors, is expediently in each case in an amount of 0.5 to 40 g / l, preferably 1 to 20 g / i, components (A) and (B) preferably in the weight ratio mentioned above are available.
  • the squeezing effect is expediently 60 to 120% by weight.
  • the aftertreatment liquors can contain mineral acids, e.g. Sulfuric acid or phosphoric acid, organic acids, suitably lower aliphatic carboxylic acid, e.g. Formic, acetic or oxalic acid and / or salts such as ammonium acetate, ammonium sulfate or sodium acetate.
  • the acids primarily serve to adjust the pH of the liquors, which can be 4 to 8, but preferably 5 to 6.
  • the liquors can also contain other common additives, e.g. Electrolytes, e.g. Contain sodium chloride or sodium sulfate, dispersing and wetting agents as well as defoamers and other cationic fixing agents, the latter also being fiber-reactive.
  • Electrolytes e.g. Contain sodium chloride or sodium sulfate, dispersing and wetting agents as well as defoamers and other cationic fixing agents, the latter also being fiber-reactive.
  • the aftertreatment of the cellulose-containing material is expediently carried out in such a way that the material, followed by dyeing but from a fresh bath, is treated with an aqueous liquor which contains components (A) and (B) and, if appropriate, acid.
  • the colored cellulose-containing materials are preferably added to a liquor which contains components (A) and (B) and acid and has a pH of 4.5 to 6 and a temperature of 25 ° C., and the colored material is treated this temperature for 5 to 25 minutes, preferably 10 to 15 minutes.
  • the temperature of the bath is then raised to 40 ° -60 ° C. and the material is treated for a further 10 to 20 minutes at this temperature.
  • the cellulose material is optionally rinsed with water and then dried in the customary manner.
  • the colored cellulose material obtained has not only improved wet fastness and rubbing fastness compared to the untreated material, but also a soft, fluffy feel. In addition, the sewability of the material is not affected. Color yield and light fastness of the dyeings are also not negatively affected.
  • the percentages relate to the weight, unless stated otherwise.
  • the amounts of the dyes relate to commercial, i.e. coupé goods and with the aids on pure substance.
  • dialkylaminoalkyl behenic acid amides or behenic acid esters listed in Table i below are prepared in an analogous manner by reacting behenic acid with the corresponding dialkylaminoalkylamine or dialkylaminoalkanol.
  • Example 1 A cotton jersey is made in the usual way using the pull-out method, with a liquor ratio of 1:20, with 2% of a dye of the formula and colored with the addition of 20 g / l sodium chloride. The goods are then rinsed warm and cold.
  • Half of the dyed goods are placed in a fresh treatment bath at a liquor ratio of 1:40, the aqueous liquor, based on the weight of the goods, being 0.2% of the diquaternary ammonium salt of the formula (101) and 0.2% of the reaction product contains from 1 mol of diethylenetriamine and 1 mol of dicyandiamide according to DE-AS 1 595 390, Example 1 and has been adjusted to pH 5.5 with acetic acid.
  • the goods are then treated at 25 ° C. for 15 minutes and the temperature is raised to 50 ° C., whereupon the goods are treated at this temperature for a further 15 minutes.
  • the goods are then dewatered and dried.
  • EXAMPLE 2 The procedure is as described in Example 1, but an aqueous preparation is used in the aftertreatment which, based on the weight of the goods, comprises 0.2% of the reaction product of 1 mol of diethylene triamine and 1 mol of dicyandiamide and 0.2% of the diquaternary ammonium salt of the formula ( 107) contains.
  • the pH is 5.5.
  • EXAMPLE 3 The procedure is as described in Example 1, but an aqueous preparation is used in the aftertreatment which, based on the weight of the goods, contains 0.45% of the diquaternary ammonium salt of the formula (101) and 0.15% of the reaction product from 1 mol of diethylene triamine and 1 Mol contains dicyandiamide. The pH is 5.5.
  • Example 4 The dyeing is carried out as described in Example 1. Then half of the dyed goods are padded on a padder with a liquor absorption of 100% with an aqueous liquor which contains 4.5 g of the diquaternary ammonium salt of the formula (107) and 1.5 g of the reaction product of 1 mol of diethylene triamine and 1 liter Mol contains dicyandiamide and has been adjusted to pH 5.5 with acetic acid. After padding, the goods are dried.
  • Example 5 100 kg of bleached cotton tricot with 3% of a dye of the formula are bleached on a reel runner in a pull-out process at a liquor ratio of 1:30 colored in the usual way. The dyeing is then rinsed cold and soaped with 1 g / l of the adduct of 10 moles of ethylene oxide and 1 mole of nonylphenol for 20 minutes at cooking temperature. The dyeing is then rinsed cold again until the wash liquor remains colorless.
  • the goods are then dewatered and dried.
  • the polyquaternary ammonium salt used in Example 5 is prepared as follows.
  • the pH of a 5% aqueous solution is 4.0.
  • Example 6 10 kg of cotton jersey are dyed in the usual manner in the exhaust process at a liquor ratio of 1:20 with 2% of a dye of the formula (201) and with the addition of 20 g / l of sodium chloride. The goods are then rinsed warm and cold.
  • the dyed goods are treated on a fresh bath in a 1:40 liquor with a preparation which, based on the weight of the goods, 0.45% of the diquaternary ammonium salt of the formula (109) and 0.15% of the polyquaternary ammonium salt with recurring units of the formula (120) contains and is adjusted to pH 5 with acetic acid.
  • the treatment is first carried out at 25 ° C and for 15 minutes. Then the temperature is raised to 50 ° C and the goods are treated for a further 15 minutes. The goods are then rinsed and dried.
  • EXAMPLE 7 The procedure is as described in Example 6, but an aqueous preparation is used in the aftertreatment which, based on the weight of the goods, contains 0.3% of the diquaternary ammonium salt of the formula (112) and 0.3% of the polyquaternary ammonium salt with repeating units of the formula (120) contains.
  • the pH is 5.
  • EXAMPLE 8 The procedure is as described in Example 6, but an aqueous preparation is used in the aftertreatment which, based on the weight of the goods, contains 0.45% of the diquaternary ammonium salt of the formula (110) and 0.15% of the polyquaternary ammonium salt with repeating units of the formula ( 120) contains.
  • the pH is 5.
  • EXAMPLE 9 The procedure is as described in Example 6, but an aqueous preparation is used in the aftertreatment, which, based on the weight of the product, 0.15% of the diquaternary ammonium salt of the formula (111), 0.3% of the polyquaternary ammonium salt with repeating units of the formula ( 120) contains.
  • the pH is 5.
  • EXAMPLE 10 The procedure is as described in Example 6, but an aqueous preparation is used in the aftertreatment, which, based on the weight of the product, is 0.45% of the diquaternary ammonium salt of the formula (112) and 0.15% of the reaction product of 1 mol of diethylene triamine and 1 mol Contains dicyandiamide. The pH is 5.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
EP86810502A 1985-11-25 1986-11-03 Verfahren zur Nachbehandlung von gefärbtem Cellulosefasermaterial Expired EP0225282B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH502185 1985-11-25
CH5021/85 1985-11-25

Publications (2)

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EP0225282A1 EP0225282A1 (de) 1987-06-10
EP0225282B1 true EP0225282B1 (de) 1989-01-25

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EP86810502A Expired EP0225282B1 (de) 1985-11-25 1986-11-03 Verfahren zur Nachbehandlung von gefärbtem Cellulosefasermaterial

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US (1) US4721512A (ja)
EP (1) EP0225282B1 (ja)
JP (1) JPS62184187A (ja)
DE (1) DE3661947D1 (ja)
ZA (1) ZA868484B (ja)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102060715A (zh) * 2010-12-22 2011-05-18 南京大学 双季铵羧酸盐功能化离子液体及其制法

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0221855B1 (de) * 1985-11-08 1990-07-11 Ciba-Geigy Ag Diquaternäre Ammoniumsalze und deren Herstellung und Verwendung als Textilveredelungsmittel
FR2679548B1 (fr) * 1991-07-25 1994-10-21 Alsthom Cge Alcatel Procede de fabrication de fibres optiques actives.
TW211595B (ja) * 1991-12-07 1993-08-21 Hoechst Ag
US5643864A (en) * 1994-08-19 1997-07-01 Rhone-Poulenc, Inc. Anionic surfactants having multiple hydrophobic and hydrophilic groups
JP2010538101A (ja) * 2007-08-31 2010-12-09 ザ プロクター アンド ギャンブル カンパニー 組成物及び視覚認識変化方法
JP5667328B2 (ja) * 2011-08-30 2015-02-12 オーシャンズ キング ライティング サイエンスアンドテクノロジー カンパニー リミテッド ２つの中心を有するビス第四級アンモニウム塩のイオン液体、その調製方法及び使用
CN116133865A (zh) * 2020-07-15 2023-05-16 山阳色素株式会社 水性喷墨油墨、通过喷墨法对纤维结构体进行印刷的方法

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US3097039A (en) * 1963-07-09 Hoas oh
DE582101C (de) * 1930-10-16 1933-08-10 Chem Ind Basel Verfahren zur Verbesserung der Echtheitseigenschaften von mit wasserloeslichen Farbstoffen gefaerbten Textilien
DE894237C (de) * 1950-09-01 1953-10-22 Geigy Ag J R Verfahren zum Verbessern der Echtheiten von Faerbungen
US2891835A (en) * 1956-10-10 1959-06-23 Ciba Ltd Diquaternary ammonium compounds used in the cationic dyeing of fibers of polyacrylonitrile
CH369110A (de) * 1959-04-10 1963-01-31 Ciba Geigy Verfahren zum Färben und Bedrucken von stickstoffhaltigen Fasern mit 1 :2-Metallkomplexverbindungen von Azofarbstoffen
US3253881A (en) * 1962-06-14 1966-05-31 Marguerite S Donahue Method of flameproofing a cellulosic textile
CH451513A (de) * 1965-03-26 1968-05-15 Ciba Geigy Verfahren zur Herstellung von neuen härtbaren stickstoffhaltigen Kondensationsprodukten
GB1150278A (en) * 1965-09-27 1969-04-30 Depaul Chemical Company Inc Improvements in or relating to Quaternary Ammonium Compounds
CH1669775A4 (ja) * 1975-12-23 1977-06-30
DE3505018A1 (de) * 1984-02-24 1985-09-05 Sandoz-Patent-GmbH, 7850 Lörrach Nachbehandlungsverfahren fuer gefaerbtes textilmaterial
JPS6427189A (en) * 1987-07-21 1989-01-30 Mitsubishi Electric Corp Roll device

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102060715A (zh) * 2010-12-22 2011-05-18 南京大学 双季铵羧酸盐功能化离子液体及其制法

Also Published As

Publication number Publication date
ZA868484B (en) 1987-06-24
US4721512A (en) 1988-01-26
DE3661947D1 (en) 1989-03-02
JPS62184187A (ja) 1987-08-12
EP0225282A1 (de) 1987-06-10
JPH0244956B2 (ja) 1990-10-05

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