EP0225282A1 - Procédé de post-traitement de matière fibreuse cellulosique teinte - Google Patents

Procédé de post-traitement de matière fibreuse cellulosique teinte Download PDF

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Publication number
EP0225282A1
EP0225282A1 EP86810502A EP86810502A EP0225282A1 EP 0225282 A1 EP0225282 A1 EP 0225282A1 EP 86810502 A EP86810502 A EP 86810502A EP 86810502 A EP86810502 A EP 86810502A EP 0225282 A1 EP0225282 A1 EP 0225282A1
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EP
European Patent Office
Prior art keywords
formula
carbon atoms
lower alkyl
ammonium salt
independently
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.)
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Application number
EP86810502A
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German (de)
English (en)
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EP0225282B1 (fr
Inventor
Rosemarie Töpfl
Heinz Abel
Jörg Binz
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.)
Novartis AG
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Ciba Geigy AG
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Publication of EP0225282A1 publication Critical patent/EP0225282A1/fr
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Publication of EP0225282B1 publication Critical patent/EP0225282B1/fr
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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
    • D06P5/00Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/02After-treatment
    • D06P5/04After-treatment with organic compounds
    • D06P5/08After-treatment with organic compounds macromolecular
    • 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
    • D06P5/00Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/02After-treatment
    • D06P5/04After-treatment with organic compounds
    • D06P5/06After-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, in particular 1 to 3, carbon atoms, such as, for example, 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 having 8 to 24 carbon atoms.
  • aliphatic carboxylic acids are 2-ethyl-hexanoic acid, capric, lauric, coconut fat, myristic, palm kernel fat , Palmitic, tallow fatty, oil, ricinoleic, linoleic, linolenic, stearic, arachic, arachidonic, behenic, erucic or lignoceric acid.
  • Behenic acid is the preferred acid.
  • 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 1 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 3 to Rs are preferably identical and are in particular methyl, ethyl, isopropyl or hydroxyethyl. Methyl is particularly preferred.
  • Xi and X 2 are preferably -HN-.
  • Z 1 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. It is the alkylene radical is preferably substituted by hydroxyl.
  • Preferred bridge members Q are particularly preferred.
  • Anions Ye include both anions of inorganic acids, such as the chloride, bromide, fluoride, iodide or sulfate ion as well as anions of organic acids, e.g. aromatic or aliphatic sulfonic acids, e.g. Benzenesulfonate, p-toluenesulfonate, chlorobenzenesulfonate, methane or ethanesulfonate ion, as well as the anions of lower carboxylic acids, e.g. Acetate, propionate or oxalate ion.
  • inorganic acids such as the chloride, bromide, fluoride, iodide or sulfate ion
  • organic acids e.g. aromatic or aliphatic sulfonic acids, e.g. Benzenesulfonate, p-toluenesulfonate, chlorobenzenesulfonate
  • Yo 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 a, m-alkanediol diglycidyl ether or alkane, diol-alkyl- or -arylsulphonate.
  • a Q-introducing compound having two functional groups such as, for example, epihalohydrin, dihaloalkanes, dihaloalkyl ethers, olefin dioxides, diepoxy compounds, such as a, m-alkanediol diglycidyl ether or alkane, diol-alkyl- or -ary
  • 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 Ci-C3 alcohols, e.g. Methanol, ethanol or the propanols; Alkylene glycols. such as. Ethylene glycol or propylene glycol; Monoalkyl ethers of glycols, e.g. Ethylene glycol monomethyl, ethyl or butyl ether and diethylene glycol monomethyl or ethyl ether; Ketones, e.g.
  • 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 can be reacted even further with an epihalohydrin and / or acidified.
  • These condensates and the corresponding starting materials are known from DE-AS 1 595 390 and can be produced by the process described there.
  • 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, triethylene tetramine, tetraethylene pentamine, pentaethylene hexamine, dipropylene triamines, 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, for example ⁇ , ⁇ '-dibromo-diet hylether or ⁇ , ⁇ '-dichlorodiethyl ether.
  • a peralkylated aliphatic di- or triamine for example ⁇ , ⁇ '-dibromo-diet hylether or ⁇ , ⁇ '-dichlorodiethyl ether.
  • Such polyquaternary ammonium salts are described for example in DE-PS 894 237.
  • Particularly preferred polyquaternary ammonium salts have the repeating unit of the formula in which Q 3 is an alkylene radical with 2 to 6 carbon atoms Ti to T 5 which is optionally interrupted by -NT s .
  • Q 3 is an alkylene radical with 2 to 6 carbon atoms Ti to T 5 which is optionally interrupted by -NT s .
  • W is the group -CH2CH2-O-CH2CH2-.
  • s is 2 to 50, preferably 3 to 30 and Y, belection is an anion of a strong inorganic or organic acid.
  • -NTs- can also be quaternized.
  • a particularly preferred polyquaternary ammonium salt for component (2) is that it is the repeating unit of the formula wherein s i 3 to 20 and Y 2 ⁇ is the bromide, sulfate or especially the chloride ion.
  • 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 with heating at 50 to 70 ° C and diluting with water to a from 20 to 40 0 / o 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 which 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 in Volume 6 (revised 3rd edition, 1975) on Pages 6268 - 6345.
  • the advantages of the method according to the invention are particularly evident in the aftertreatment of dyeings with noun dyes. 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 such as open baths, reel runners, jiggers, paddles, nozzles or circulation machines, 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 padding liquors, in each case expediently in an amount of 0.5 to 40 g / l, preferably 1 to 20 g / l, components (A) and (B) preferably being present in the weight ratio mentioned above.
  • the squeezing effect is appropriately 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 may also contain further customary additives, for example electrolytes such as sodium chloride or sodium sulfate, dispersants and wetting agents and defoamers and other cationic fixing agents include, the latter also may be also maschinereakt v i.
  • electrolytes such as sodium chloride or sodium sulfate
  • dispersants and wetting agents and defoamers and other cationic fixing agents include, the latter also may be also turareakt v i.
  • 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.
  • 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 5 100 kg of bleached cotton jersey 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 pH is 5.5.
  • the goods are then dewatered and dried.
  • the polyquaternary ammonium salt used in Example 5 is prepared as follows.
  • 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.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
EP86810502A 1985-11-25 1986-11-03 Procédé de post-traitement de matière fibreuse cellulosique teinte Expired EP0225282B1 (fr)

Applications Claiming Priority (2)

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

Publications (2)

Publication Number Publication Date
EP0225282A1 true EP0225282A1 (fr) 1987-06-10
EP0225282B1 EP0225282B1 (fr) 1989-01-25

Family

ID=4286577

Family Applications (1)

Application Number Title Priority Date Filing Date
EP86810502A Expired EP0225282B1 (fr) 1985-11-25 1986-11-03 Procédé de post-traitement de matière fibreuse cellulosique teinte

Country Status (5)

Country Link
US (1) US4721512A (fr)
EP (1) EP0225282B1 (fr)
JP (1) JPS62184187A (fr)
DE (1) DE3661947D1 (fr)
ZA (1) ZA868484B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2679548A1 (fr) * 1991-07-25 1993-01-29 Alsthom Cge Alcatel Procede de fabrication de fibres optiques actives.

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0221855B1 (fr) * 1985-11-08 1990-07-11 Ciba-Geigy Ag Sels d'ammonium diquaternaire, leur préparation et leur utilisation comme agent de finition pour textiles
TW211595B (fr) * 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
WO2009027925A2 (fr) * 2007-08-31 2009-03-05 The Procter & Gamble Company Procédés visant à modifier une perception visuelle et compositions associées
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
US9202632B2 (en) * 2011-08-30 2015-12-01 Ocean's King Lighting Science & Technology Co., Ltd. Double-center quaternary ammonium salt ion liquid, preparation method therefor and use thereof
JPWO2022014454A1 (fr) * 2020-07-15 2022-01-20

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
DE1281998B (de) * 1959-04-10 1968-11-07 Ciba Geigy Verfahren zum Faerben oder Bedrucken von stickstoffhaltigen Fasern
GB1150278A (en) * 1965-09-27 1969-04-30 Depaul Chemical Company Inc Improvements in or relating to Quaternary Ammonium Compounds
DE2657582A1 (de) * 1975-12-23 1977-07-07 Ciba Geigy Ag Polymere quaternaere ammoniumsalze, verfahren zu ihrer herstellung und ihre verwendung
DE3505018A1 (de) * 1984-02-24 1985-09-05 Sandoz-Patent-GmbH, 7850 Lörrach Nachbehandlungsverfahren fuer gefaerbtes textilmaterial

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3097039A (en) * 1963-07-09 Hoas oh
US2891835A (en) * 1956-10-10 1959-06-23 Ciba Ltd Diquaternary ammonium compounds used in the cationic dyeing of fibers of polyacrylonitrile
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
JPS6427189A (en) * 1987-07-21 1989-01-30 Mitsubishi Electric Corp Roll device

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
DE1281998B (de) * 1959-04-10 1968-11-07 Ciba Geigy Verfahren zum Faerben oder Bedrucken von stickstoffhaltigen Fasern
GB1150278A (en) * 1965-09-27 1969-04-30 Depaul Chemical Company Inc Improvements in or relating to Quaternary Ammonium Compounds
DE2657582A1 (de) * 1975-12-23 1977-07-07 Ciba Geigy Ag Polymere quaternaere ammoniumsalze, verfahren zu ihrer herstellung und ihre verwendung
DE3505018A1 (de) * 1984-02-24 1985-09-05 Sandoz-Patent-GmbH, 7850 Lörrach Nachbehandlungsverfahren fuer gefaerbtes textilmaterial

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2679548A1 (fr) * 1991-07-25 1993-01-29 Alsthom Cge Alcatel Procede de fabrication de fibres optiques actives.

Also Published As

Publication number Publication date
JPS62184187A (ja) 1987-08-12
US4721512A (en) 1988-01-26
JPH0244956B2 (fr) 1990-10-05
EP0225282B1 (fr) 1989-01-25
ZA868484B (en) 1987-06-24
DE3661947D1 (en) 1989-03-02

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