EP0250365A1 - Procédé de post-traitement d'une matière fibreuse cellulosique teinte - Google Patents

Procédé de post-traitement d'une matière fibreuse cellulosique teinte Download PDF

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Publication number
EP0250365A1
EP0250365A1 EP87810336A EP87810336A EP0250365A1 EP 0250365 A1 EP0250365 A1 EP 0250365A1 EP 87810336 A EP87810336 A EP 87810336A EP 87810336 A EP87810336 A EP 87810336A EP 0250365 A1 EP0250365 A1 EP 0250365A1
Authority
EP
European Patent Office
Prior art keywords
aftertreatment
minutes
formula
dye
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
EP87810336A
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German (de)
English (en)
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EP0250365B1 (fr
Inventor
Rosemarie Töpfl
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
Original Assignee
Ciba Geigy AG
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Publication date
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Publication of EP0250365A1 publication Critical patent/EP0250365A1/fr
Application granted granted Critical
Publication of EP0250365B1 publication Critical patent/EP0250365B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • 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
    • D06P1/52—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 synthetic macromolecular substances
    • D06P1/5207—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • D06P1/5214—Polymers of unsaturated compounds containing no COOH groups or functional derivatives thereof
    • D06P1/5242—Polymers of unsaturated N-containing compounds

Definitions

  • the present invention relates to a method for the aftertreatment of colored cellulose fiber material, in particular cellulose-containing textile material.
  • Dyeing and printing with substantive dyes often show inadequate wet fastness properties, especially washing and water fastness.
  • the dye which is covalently bonded to the surface of the cellulose can be removed again by repeated washing operations and the bled-out dye can again be drawn onto undyed textile material which is washed in the same wash cycle.
  • a new aftertreatment process has now been developed, which in particular significantly improves the wet fastness of cellulose dyeings which have been produced using substantive dyes.
  • fastness to washing can be improved under alkaline conditions at temperatures above 50 ° C and especially in today's usual 60 ° C washes with detergents containing sodium perborate (ISO 105 / C06 C2S).
  • detergents containing sodium perborate ISO 105 / C06 C2S
  • the present invention therefore relates to a process for the aftertreatment of colored cellulose-containing fiber material, which is characterized in that this material is treated with an aqueous liquor which contains a polyquaternary ammonium compound which, by the action of an epihalohydrin on a linear polymer, comprises the repeating units of the formula wherein R is C1-C6-alkyl, has, is obtained.
  • Suitable alkyl groups for R are methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-amyl, isoamyl, tert.amyl, hexyl, 2-ethylbutyl. Ethyl and especially methyl are preferred.
  • Polymers with units of the formula (1) can be obtained by polymerizing the hydrohalide salt of a diallylamine of the formula wherein R has the meaning given, preferably in the presence of a free radical catalyst and then neutralizing the salt, for example with aqueous sodium hydroxide solution to the polymeric free base.
  • hydrohalide salts of diallylamines which can be polymerized to give polymers of the formula (1) N-methyldiallylamine hydrochloride, N-methyldiallylamine hydrobromide, N-ethyldiallylamine hydrochloride, N-ethyl diallylamine hydrobromide, N-isopropyldiallylamine hydrochloride, Nn-butyldiallylamine hydrobromide, N-tert-butyldiallylamine hydrochloride, Nn-hexyldiallylamine hydrochloride.
  • Suitable free radical-forming catalysts are symmetrical peroxide dicarbonates, peroxide dicarbamates, perbenzoates, perborates, persulfates or peroxide sulfates.
  • the preferred catalyst is potassium persulfate and also azobis-isobutyronitrile or, above all, azo-bis (2-amidinopropane) hydrochloride.
  • These catalysts can be used in amounts of 0.05 to 5% by weight, advantageously 0.5 to 2% by weight, based on the N-alkyldiallylamine.
  • the epihalohydrin which is reacted with the N-alkyl-diallylamine polymer can be any epihalohydrin, e.g. Epibromohydrin, Epifluorhydrin, Epijodhydrin, ß-Methylepichlorhydrin or preferably epichlorohydrin.
  • the epihalohydrin is used in an amount of 0.5 to 1.5 mol, preferably 1 to 1.5 mol, per mol of the sum of tertiary amine in the polymer.
  • reaction conditions for the preparation of the polyquaternary polymers are to be chosen such that there is no premature exchange of movable substituents either as a result of the pH of the reaction medium being too high or as a result of the temperature being too high. It is therefore preferred to work in a dilute, aqueous medium under as mild a temperature and pH conditions as possible, advantageously at a temperature of 30 to 85 ° C. and a pH of 6 to 8.5, preferably 7 to 8, in order to achieve the desired pH -Value and a hydrohalic acid, preferably hydrochloric acid is used to form the hydrohalide salt.
  • 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 can be used in any form, e.g. Flakes, yarns, packages, yarn strands, fabrics, knitted fabrics or felts that are made entirely or partially of native or regenerated cellulose.
  • the cellulose fiber material is generally dyed with reactive dyes or, preferably, with substantive dyes. You can use the pull-out procedure or two-stage processes such as the padding process or printing are produced, the padding process, in particular the so-called pad-steam process, thermofix process or the pad-cold dwelling process being considered.
  • the amount of dyes used depends on the desired depth of color. In general, amounts of 0.1 to 10% by weight, in particular 0.5 to 5% 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 mean the usual dyes which form a chemical bond with the cellulose, for example those in Color Index, in volume 3 (3rd edition, 1971) on pages 3391-3560 and in volume 6 (revised 3rd edition, 1975 ) "Reactive Dyes” listed on pages 6268-6345.
  • the aftertreatment according to the invention is preferably carried out using the exhaust process.
  • the liquor ratio can be chosen within a wide range e.g. 1: 4 to 1: 100, preferably 1: 5 to 1:40.
  • Special devices are not required.
  • the usual dyeing machines e.g. open baths, reel runners, jiggers, paddle, jet or circulation devices can be used.
  • the treatment time can be 20 to 60 minutes, but in most cases a treatment time of 30 to 40 minutes is sufficient. It expediently comprises 15 to 20 minutes of treatment with the cationic aftertreatment agent, then addition of the alkali and a further 15 to 20 minutes of treatment to fix the aftertreatment agent.
  • the aftertreatment agent is advantageously used in an amount of 0.5 to 5% by weight, preferably 0.8 to 2% by weight active ingredient content, based on the weight of the cellulose material, to achieve the desired fastness standard.
  • the liquors used according to the invention also contain alkaline compounds, such as sodium hydroxide or potassium hydroxide.
  • alkaline compounds such as sodium hydroxide or potassium hydroxide.
  • a 30% aqueous sodium hydroxide solution is preferably added in an amount of 2 to 10 ml / l, preferably 4 to 6 ml / l liquor puts.
  • the alkali can be added to the liquor at the beginning with the cationic aftertreatment agent or preferably only after 15 to 20 minutes with the aftertreatment agent.
  • the pH of the treatment liquors can therefore generally be 8 to 13.5, preferably 10.5 to 13.
  • 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 the aftertreatment agent, alkali and optionally an electrolyte, preferably sodium sulfate.
  • the dyed cellulose-containing materials are preferably added to a liquor which contains aftertreatment agents and sodium sulfate and has a temperature of 30 ° C., and the dyed material is treated at this temperature for 15 to 20 minutes, preferably 15 minutes. An alkali is added and the material is treated for a further 15 to 20 minutes at 30 ° C.
  • the cellulose material is optionally rinsed with water, optionally neutralized with acetic acid and then dried in a customary manner.
  • the process according to the invention gives dyeings and prints on cellulose fiber material which have been produced using reactive and, in particular, substantive dyes and which show a considerable improvement in wet fastness properties, such as washing and water fastness.
  • the color yield, shade and light fastness of the dyeings are not adversely affected.
  • the post-treated dyeings and prints show no stiffening.
  • the percentages relate to the weight, unless stated otherwise.
  • the amounts of the dyes relate to commercial, i.e. Coucher goods and with the auxiliaries on active substance.
  • Example 1 101.4 g of 30% hydrochloric acid are added dropwise to 92.5 g of N-methyldiallylamine at 20 ° C. in the course of 30 minutes and the mixture is stirred until a homogeneous solution has formed. The temperature is then increased to 60 ° C. and 13.5 g of a 10% strength aqueous potassium persulfate solution are added to the solution, whereupon the temperature rises to 80 ° C. in the course of 45 minutes. The mixture is subsequently polymerized at 70 ° C. for 5 hours and diluted with 696.75 g of water, the viscosity, measured in a Brookfield LV type viscometer, 25 ° C., being 850 mPas before dilution.
  • the mixture is cooled to 40 ° C. and adjusted to a pH of 7.8 by adding 11 g of a 30% strength aqueous sodium hydroxide solution. Then 77 g of epichlorhyrin are added dropwise at 50 ° C. in 20 minutes and stirring is continued for one hour. Then 20 g of 37% hydrochloric acid are added and the mixture is stirred cold. 1012 g of a clear, low-viscosity solution are obtained, the active ingredient content of which is 16.7%.
  • Example 2 98.64 g of 37% hydrochloric acid are added dropwise to 125 g of N-ethyldiallylamine over a period of 30 minutes at a maximum of 20 ° C., and the mixture is stirred until a homogeneous solution has formed. Thereupon the temperature is increased to 60 ° C. and the solution is mixed with 9.35 g of a 10% strength aqueous solution of 2,2′-azobis- (2-amidinopropane) dihydrochloride, whereupon the temperature in the course of Rises to 85 ° C for 60 minutes.
  • Example 3 88.8 g of 37% hydrochloric acid are added dropwise over a period of 30 minutes at a maximum of 20 ° C. to 125 g of N-isopropyldiallylamine and the mixture is stirred until a homogeneous solution has formed. The temperature is then increased to 60 ° C. and the solution is mixed with 9.38 g of a 10% strength aqueous solution of 2,2′-azobis- (2-amidinopropane) dihydrochloride, whereupon the temperature is raised to 71 ° in the course of 50 minutes C increases.
  • a red color is obtained which has excellent acid fastness to hydrolysis.
  • Example 3 The dyeings according to Example 2 (A) with subsequent aftertreatment (B) are repeated, the impregnated goods being exposed to dry heat on a hot air fixer for 2 minutes at 210 ° C. after the padding. After the aftertreatment, the water fastness test is carried out strictly (SN ISO 105 / E01) with multi-fiber tape as accompanying fabric. The results of these tests are shown in Table 3.
  • EXAMPLE 4 The procedure is as described in Example 1, but 2.4% of the reaction product according to Preparation Example 2 is used for the aftertreatment instead of the reaction product according to Preparation Example 1.
  • a cheese bobbin of 500 g of bleached cotton yarn is dyed at a liquor ratio of 1:20 with an aqueous dye liquor which contains 2% of a dye of the formula (102). It starts at 40 ° C and increases the temperature in the course of 30 minutes at 98 ° C. Then 3 portions of 6.5 g / l sodium sulfate are added at intervals of 5 minutes each, followed by further dyeing at 98 ° C. for 45 minutes. The dyeing is then rinsed with water at 40 ° C. for 10 minutes and with cold water for 10 minutes, then treated with 1.2% of the reaction product according to Preparation Example 1 as described in Example 5 (B). The ISO C2S wash is checked from this post-treated dyeing, and a corresponding dyeing, which is post-treated with 3% Tinofix EWA, is also checked.
  • Table 6 shows the results of the tests.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Coloring (AREA)
EP87810336A 1986-06-17 1987-06-11 Procédé de post-traitement d'une matière fibreuse cellulosique teinte Expired - Lifetime EP0250365B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH243786 1986-06-17
CH2437/86 1986-06-17

Publications (2)

Publication Number Publication Date
EP0250365A1 true EP0250365A1 (fr) 1987-12-23
EP0250365B1 EP0250365B1 (fr) 1990-05-09

Family

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Family Applications (1)

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EP87810336A Expired - Lifetime EP0250365B1 (fr) 1986-06-17 1987-06-11 Procédé de post-traitement d'une matière fibreuse cellulosique teinte

Country Status (9)

Country Link
US (1) US4822374A (fr)
EP (1) EP0250365B1 (fr)
JP (1) JPH0672368B2 (fr)
DE (1) DE3762634D1 (fr)
ES (1) ES2014494B3 (fr)
HK (1) HK50291A (fr)
PT (1) PT85094B (fr)
SG (1) SG36491G (fr)
ZA (1) ZA874310B (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5320648A (en) * 1991-12-20 1994-06-14 Ciba-Geigy Corporation Process for dyeing or printing hydroxyl group containing fibre materials
US5542956A (en) * 1991-12-20 1996-08-06 Ciba-Geigy Corporation Process for dyeing or printing hydroxyl group containing fiber materials
DE19509982A1 (de) * 1995-03-18 1996-09-19 Sandoz Ag Textilnachbehandlungsmittel
DE10027624A1 (de) * 2000-06-02 2001-12-06 Zschimmer & Schwarz Mohsdorf G Verfahren zur Nachreinigung von gefärbten oder bedruckten polyesterhaltigen textilen Produkten und Mischung zur Durchführung des Verfahrens

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9013784D0 (en) * 1990-06-20 1990-08-08 Unilever Plc Process and composition for treating fabrics
CN101310076A (zh) * 2005-11-11 2008-11-19 西巴控股有限公司 纸张表面着色方法
AT508846B1 (de) * 2009-09-17 2012-02-15 Chemiefaser Lenzing Ag Fluoreszierende faser, deren verwendung sowie verfahren zu deren herstellung
WO2018190328A1 (fr) * 2017-04-14 2018-10-18 日東紡績株式会社 Améliorant de solidité au frottement humide pour fibres à base de cellulose, procédé de production de fibre de cellulose colorée l'utilisant et son utilisation

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3686151A (en) * 1971-01-18 1972-08-22 Hercules Inc Terpolymers of diallylamine
DE3216913A1 (de) * 1981-05-14 1982-12-02 Sandoz-Patent-GmbH, 7850 Lörrach Textilhilfsmittel und verfahren zum faerben von textilmaterial
DE3320629A1 (de) * 1983-06-08 1984-12-13 Basf Ag, 6700 Ludwigshafen Verfahren zum faerben von textilen materialien aus hydrophilen fasern
EP0142337A1 (fr) * 1983-11-15 1985-05-22 Nitto Boseki Co., Ltd. Procédé pour la solidité de teinture

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3966694A (en) * 1973-02-21 1976-06-29 Hercules Incorporated Cationic water soluble polymeric reaction product of poly(diallylamine)-epihalohydrin and nitrogen compound
JPS5370178A (en) * 1976-12-01 1978-06-22 Nippon Senka Kougiyou Kk Improving of dyeing fastness
US4511707A (en) * 1981-05-14 1985-04-16 Sandoz Ltd. Water-soluble precondensates useful for improving the fastness of dyes and optical brighteners on hydroxy group-containing substrates
JPS6071786A (ja) * 1983-09-28 1985-04-23 第一工業製薬株式会社 染色堅牢度向上方法
DE3416693A1 (de) * 1984-05-05 1985-11-07 Bayer Ag, 5090 Leverkusen Verfahren zur behandlung von cellulosischen fasermaterialien
DE3417240A1 (de) * 1984-05-10 1985-11-14 Basf Ag, 6700 Ludwigshafen Verfahren zur nachbehandlung von gefaerbten textilen materialien aus natuerlichen oder synthetischen polyamiden
JPS61231283A (ja) * 1985-04-01 1986-10-15 日東紡績株式会社 染色堅牢度向上法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3686151A (en) * 1971-01-18 1972-08-22 Hercules Inc Terpolymers of diallylamine
DE3216913A1 (de) * 1981-05-14 1982-12-02 Sandoz-Patent-GmbH, 7850 Lörrach Textilhilfsmittel und verfahren zum faerben von textilmaterial
DE3320629A1 (de) * 1983-06-08 1984-12-13 Basf Ag, 6700 Ludwigshafen Verfahren zum faerben von textilen materialien aus hydrophilen fasern
EP0142337A1 (fr) * 1983-11-15 1985-05-22 Nitto Boseki Co., Ltd. Procédé pour la solidité de teinture

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Band 103, Nr. 16, Oktober 1985, Seite 75, Zusammenfassung Nr. 124944a, Columbus, Ohio, US; & JP-A-60 71 786 (DAIICHI KOGYO SEIYAKU CO., LTD) 23-04-1985 *
CHEMICAL ABSTRACTS, Band 87, Nr. 18, Oktober 1977, Seite 62, Zusammenfassung Nr. 137246a, Columbus, Ohio, US; & JP-A-77 59 787 (NITTO BOSEKI CO., LTD) 17-05-1977 *
CHEMICAL ABSTRACTS, Band 94, Nr. 16, April 1981, Seite 81, Zusammenfassung Nr. 123043q, Columbus, Ohio, US; & JP-A-80 152 879 (NITTO BOSEKI CO., LTD) 28-11-1980 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5320648A (en) * 1991-12-20 1994-06-14 Ciba-Geigy Corporation Process for dyeing or printing hydroxyl group containing fibre materials
US5542956A (en) * 1991-12-20 1996-08-06 Ciba-Geigy Corporation Process for dyeing or printing hydroxyl group containing fiber materials
DE19509982A1 (de) * 1995-03-18 1996-09-19 Sandoz Ag Textilnachbehandlungsmittel
WO1996029463A1 (fr) * 1995-03-18 1996-09-26 Clariant Finance (Bvi) Limited Agents de fixation de teintures pour textiles
AU703289B2 (en) * 1995-03-18 1999-03-25 Clariant Finance (Bvi) Limited Textile dye-fixing agents
US5908474A (en) * 1995-03-18 1999-06-01 Clariant Finance (Bvi) Limited Textile dye-fixing agents
CN1077936C (zh) * 1995-03-18 2002-01-16 克莱里安特财务(Bvi)有限公司 纺织固色剂
DE10027624A1 (de) * 2000-06-02 2001-12-06 Zschimmer & Schwarz Mohsdorf G Verfahren zur Nachreinigung von gefärbten oder bedruckten polyesterhaltigen textilen Produkten und Mischung zur Durchführung des Verfahrens

Also Published As

Publication number Publication date
ZA874310B (en) 1987-12-17
US4822374A (en) 1989-04-18
JPH0672368B2 (ja) 1994-09-14
PT85094B (pt) 1990-03-08
EP0250365B1 (fr) 1990-05-09
ES2014494B3 (es) 1990-07-16
DE3762634D1 (de) 1990-06-13
HK50291A (en) 1991-07-12
SG36491G (en) 1991-06-21
PT85094A (en) 1987-07-01
JPS62299589A (ja) 1987-12-26

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