EP0160872B1 - Procédé de traitement de matières fibreuses cellulosiques - Google Patents

Procédé de traitement de matières fibreuses cellulosiques Download PDF

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Publication number
EP0160872B1
EP0160872B1 EP85104821A EP85104821A EP0160872B1 EP 0160872 B1 EP0160872 B1 EP 0160872B1 EP 85104821 A EP85104821 A EP 85104821A EP 85104821 A EP85104821 A EP 85104821A EP 0160872 B1 EP0160872 B1 EP 0160872B1
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EP
European Patent Office
Prior art keywords
polyether
parts
process according
dyeing
polyethers
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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
EP85104821A
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German (de)
English (en)
Other versions
EP0160872A2 (fr
EP0160872A3 (en
Inventor
Helmut Dr. Engelhard
Heinz-Dieter Feuser
Udo Dr. Hendricks
Ergun Dipl.-Ing. Tamer
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Bayer AG
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Bayer AG
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Publication of EP0160872A3 publication Critical patent/EP0160872A3/de
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/53—Polyethers
    • 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
    • D06P1/60—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 polyethers
    • D06P1/607—Nitrogen-containing polyethers or their quaternary derivatives
    • 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

Definitions

  • R and R 2 the methyl, ethyl, n-propyl, iso-propyl, n-butyl and sec-butyl radicals may be mentioned as C 1 -C 4 -alkyl radicals.
  • R is C, -C 4 alkyl or cyclohexyl and R 1 and R 2 are hydrogen or methyl.
  • the average molecular weight of the polyethers to be used according to the invention should be between 500 and 20,000, preferably 1,000 to 15,000.
  • the polyethers to be used according to the invention are linear or slightly branched polyethers.
  • the linear polyethers can be prepared by known methods by condensation of N-2-hydroxyalkylamines of the formula I in the presence of acidic catalysts, e.g. B. H 3 P0 3 , at elevated temperatures, e.g. B. 150-280 ° C can be obtained.
  • acidic catalysts e.g. B. H 3 P0 3
  • elevated temperatures e.g. B. 150-280 ° C
  • the diols containing tertiary amino groups are condensed together with triols containing tertiary amino groups, ie N-2-hydroxyalkylamines of the formula I in which R represents one of the ⁇ -hydroxyalkyl groups indicated.
  • the amount of triols in the condensation mixture should not be more than 20 percent by weight, preferably 2-15 percent by weight.
  • polyethers to be used according to the invention are known, for example, from GB-A-1 107 818, DE-A-2 060 572 and EP-A-0 057 398.
  • ⁇ -hydroxyalkylamines of the formula (I) which may be mentioned are the N-di- (2-hydroxyalkyl) amines as used in the addition of ethylene, propylene and butylene oxide or mixtures of these alkylene oxides to primary aliphatic, cycloaliphatic, araliphatic and aromatic amines are formed.
  • N-di- (2-hydroxyalkyl) amines (I) are, for example:
  • Triethanolamine, triisopropanolamine and tributanolamine may be mentioned in particular as representatives of the triols used to prepare the branched polyethers.
  • the quaternization is carried out in a manner known per se by reacting the polyethers which are optionally dissolved or suspended in alcohol / water mixtures with known alkylating agents, such as dimethyl sulfate or diethyl sulfate; p-Toluenesulfonic acid alkyl esters, e.g. B. methyl p-toluenesulfonate; Alkyl halides, e.g. B.
  • methyl iodide or ethyl bromide Chloroacetamide, halocarboxylic acid salts, halocarboxylic acid esters, alkane sultones, benzyl chloride, methanephosphonic acid dimethyl ester, trimethyl phosphate or alkylene oxide such as ethylene oxide and propylene oxide in the presence of acids.
  • the amounts in which the quaternized polyethers to be used according to the invention are added to the aqueous liquors can vary within wide limits. In general, an addition of 0.1-2%, preferably 0.2-1%, based on the weight of the fiber materials, has proven useful.
  • the quaternized polyethers can be applied in a pretreatment process to the untreated fiber material to be dyed or printed in order to improve the color yield by impregnating or printing with aqueous liquors which contain the quaternized polyethers.
  • the fiber material thus treated is z. B. squeezed to a liquor intake of 60 - 100%, dried and, if necessary after heat treatment, for. B. by brief steaming at 102 - 120 °, colored or printed in the usual way.
  • the aftertreatment of the dyed or printed fiber material to improve wet fastness is carried out either in the exhaust process by the dyed or printed material z. B. for 20 - 30 minutes in an aqueous liquor containing the quaternized polyethers to be used according to the invention and having a pH of z. B. 4 - 8, preferably 5.5 - 6.5, and a temperature of 20 - 40 ° C, or the fleet used for aftertreatment continuously, for. B. by means of a foulard, applied to the colored or printed material.
  • Suitable dyes for the production of dyeings and prints are e.g. B. in the Color Index, 3rd edition (1971), Vol. 2 on pages 2005-2478 as direct dyes and on pages 1001-1562 as acid dyes.
  • Suitable reactive dyes are e.g. B. in Venkataraman, The Chemistry of Synthetic Dyes, Volume VI, Reactive Dyes (Academic Press, New York, London 1972).
  • Fiber materials suitable according to the invention are, above all, those made from natural or regenerated cellulose; Cotton, hemp, jute, linen, as well as viscose and cellulose acetate fibers and blended fabrics containing cellulose fibers are mentioned.
  • the fiber material can be in various processing states and z. B. present as loose material, yarn, fabric or knitted fabric.
  • the color yield and the fastness properties of dyeings and prints are considerably improved.
  • cyanamide derivatives and formaldehyde often used to improve wet fastness properties, such as those used for. B. in US Pat. No. 3,290,310 or in Rev. Prog. Coloration Vol. 12 (1982), pp. 76-77, offer the invention
  • Compounds have the advantage of total freedom from formaldehyde.
  • Another advantage of the claimed compounds is the slight impairment of the handle of the treated fiber materials and the lightfastness of the dyeings. Furthermore, they do not cause color changes in the colorings.
  • Polyether B was produced analogously to polyether A, except that instead of the 82 parts of dimethyl sulfate, only 54 parts of dimethyl sulfate (0.5 mol of dimethyl sulfate per mole of basic amino group) were used for the quaternization.
  • the quaternization product remains as a yellow water-soluble syrup.
  • Polyether C was prepared analogously to polyether A, except that 108 parts of dimethyl sulfate (1.0 mol of dimethyl sulfate per mol of basic amino group) were used instead of the 82 parts of dimethyl sulfate for the quaternization.
  • the quaternization product remains as a yellow water-soluble syrup.
  • the polyether can be represented by the formula describe.
  • a cotton fabric is treated on a reel runner in a liquor ratio of 1:20 at 40 ° C with a dyeing liquor, which is in liters
  • a cotton fabric is treated on a reel runner in a liquor ratio 1:20 at 25 ° C. with a dyeing liquor which contains 2 g per liter of the red dye of DE-A 2 264 698, example 3.
  • the dye bath is heated to 40 ° C. in the course of 30 minutes and then 50 g / l of sodium sulfate and, after a further 10 minutes, 20 g / l of sodium carbonate are added, and the dyeing is carried out at 40 ° C. for 1 hour. Then it is rinsed cold, hot and boiling.
  • the dyeing is then treated with the polyether A in a fresh bath as described in Example 1.
  • a cotton fabric is dyed, rinsed, soaped and dried as described in Example 3.
  • Example 3 The dyeing is then treated as in Example 2. As a result of the aftertreatment, the wet fastness level is significantly improved, as in Example 3.
  • the material pretreated in this way is then dyed and rinsed as described in Example 1.
  • the printed areas show a significantly deeper staining than the unprinted areas.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Coloring (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polyethers (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Claims (7)

1. Procédé pour le traitement de matières fibreuses cellulosiques par des bains aqueux avant ou après teinture ou impression par des colorants substantifs ou des colorants réactifs, caractérisé en ce que les bains aqueux contiennent des polyéthers quaternisés qui ont été obtenus par condensation de N-2-hydroxyalkylamines de formule:
Figure imgb0017
dans laquelle
R, et R2 représentent chacun, indépendamment l'un de l'autre, l'hydrogène ou un groupe alkyle en Cl-C4 et
R représente un groupe alkyle en C1-C18, cycloalkyle, aralkyle ou aryle ou l'un des groupes hydroxyalkyles
Figure imgb0018
sous réserve que la quantité de N-2-hydroxyalkylamines dans lesquelles R représente un groupe hydroxyalkyle ne représente pas plus de 20 % du poids des hydroxyalkylamines mises en oeuvre, éventuellement par co-condensation avec des polyols de formule
Figure imgb0019
dans laquelle
A représente un radical aliphatique, cycloaliphatique, araliphatique ou aromatique di-, tri- ou tétravalent et
n est un nombre allant de 2 à 4,
en faisant suivre d'une quaternisation.
2. Procédé selon la revendication 1, caractérisé en ce que les polyéthers ont un poids moléculaire de 500 à 20 000.
3. Procédé selon la revendication 1, caractérisé en ce que les polyéthers sont préparés à partir de N-2-hydroxyalkylamines de formule indiquée dans la revendication 1, dans laquelle R représente un groupe alkyle en Cl-C4 ou cyclohexyle et R1 et R2 représentent l'hydrogène ou des groupes méthyles.
4. Procédé selon la revendication 1, caractérisé en ce que les bains contiennent de 0,1 à 2 % en poids du polyéther.
5. Procédé selon la revendication 1, caractérisé en ce que les matières fibreuses sont traitées par les bains aqueux, par la technique d'épuisement, après teinture ou impression.
6. Procédé selon la revendication 1, caractérisé en ce que les matières fibreuses sont traitées par les bains aqueux dans un mode opératoire continu après teinture ou impression.
7. Procédé selon la revendication 1, caractérisé en ce que les matières fibreuses non traitées sont traitées par les bains aqueux avant teinture ou impression.
EP85104821A 1984-05-05 1985-04-20 Procédé de traitement de matières fibreuses cellulosiques Expired EP0160872B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19843416693 DE3416693A1 (de) 1984-05-05 1984-05-05 Verfahren zur behandlung von cellulosischen fasermaterialien
DE3416693 1984-05-05

Publications (3)

Publication Number Publication Date
EP0160872A2 EP0160872A2 (fr) 1985-11-13
EP0160872A3 EP0160872A3 (en) 1987-05-20
EP0160872B1 true EP0160872B1 (fr) 1988-11-02

Family

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Family Applications (1)

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EP85104821A Expired EP0160872B1 (fr) 1984-05-05 1985-04-20 Procédé de traitement de matières fibreuses cellulosiques

Country Status (4)

Country Link
US (1) US4629468A (fr)
EP (1) EP0160872B1 (fr)
JP (1) JPS60239579A (fr)
DE (2) DE3416693A1 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3537458A1 (de) * 1985-10-22 1987-04-23 Basf Ag Verfahren zur nachbehandlung von reaktivfaerbungen auf cellulosefasern
US4822374A (en) * 1986-06-17 1989-04-18 Ciba-Geigy Corporation Process for the aftertreatment of dyed cellulose fibers
IL94466A (en) * 1989-05-25 1995-01-24 Erba Carlo Spa Pharmaceutical preparations containing the history of A-amino carboxamide N-phenylalkyl are converted into such new compounds and their preparation
US5298584A (en) * 1990-12-14 1994-03-29 The United States Of America As Represented By The Secretary Of Agriculture Anionically dyeable smooth-dry crosslinked cellulosic material created by treatment of cellulose with reactive swelling agents and nitrogen based compounds
US5698476A (en) * 1995-03-01 1997-12-16 The Clorox Company Laundry article for preventing dye carry-over and indicator therefor
WO2009060409A1 (fr) * 2007-11-09 2009-05-14 The Procter & Gamble Company Compositions de nettoyage avec des polyalcanolamines alcoxylées
CN101855273B (zh) * 2007-11-09 2013-01-30 巴斯夫欧洲公司 烷氧基化的聚链烷醇胺
EP2199315B1 (fr) 2008-12-19 2013-12-11 Basf Se Composition comprenant un agent égalisant pour électrodeposition
CN116113657A (zh) 2020-12-16 2023-05-12 巴斯夫欧洲公司 作为润湿剂以及作为消泡剂组合物的组分的烷氧基化聚合n-(羟烷基)胺

Family Cites Families (15)

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Publication number Priority date Publication date Assignee Title
US2096534A (en) * 1937-10-19 Quaternary ammonium compounds
GB460961A (en) * 1935-07-05 1937-02-05 Ig Farbenindustrie Ag Process for improving the fastness of dyeings
FR828619A (fr) * 1936-11-10 1938-05-24 Prod Chim Fab De Produits de condensation basiques et procédé de préparation de ces produits
GB969159A (fr) * 1963-02-20
DE1469737A1 (de) * 1965-09-30 1969-01-02 Bayer Ag Verfahren zum Faerben von Polyacrylnitrilgebilden
DE2060572A1 (de) * 1970-12-09 1972-06-22 Bayer Ag Verfahren zum Herabsetzen der Farbstoffaffinitaet von Fasermaterialien aus Polyacrylnitril
DE2407147A1 (de) * 1974-02-15 1975-08-28 Bayer Ag Quartaere n- (2,3-epoxyalkyl)-ammonium- verbindungen
US4198269A (en) * 1976-01-26 1980-04-15 The Dow Chemical Company Quaternary ammonium salts of epihalohydrin polymers as additives for fibrous cellulosic materials
DE2747358C2 (de) * 1977-10-21 1986-12-04 Bayer Ag, 5090 Leverkusen Verfahren zur Nachbehandlung von Reaktivfärbungen
DE2843645A1 (de) * 1978-10-06 1980-04-17 Basf Ag Verfahren zum auswaschen von nicht fixierten reaktivfarbstoffen von cellulosefasern
JPS5571884A (en) * 1978-11-27 1980-05-30 Nippon Senka Kogyo Kk Enhancing of dye fastness
DE3105897A1 (de) * 1980-02-22 1982-03-11 Sandoz-Patent-GmbH, 7850 Lörrach Faerbehilfsmittel und verfahren zum faerben von cellulosefasern
NL8104330A (nl) * 1980-09-24 1982-04-16 Sandoz Ag Werkwijze voor het wasecht maken van cellulose-bevattend textiel en daarbij te gebruiken stoffen.
CH660940GA3 (fr) * 1981-01-10 1987-06-30
DE3103815A1 (de) * 1981-02-04 1982-09-09 Bayer Ag, 5090 Leverkusen Verfahren zur nachbehandlung von gefaerbten, filzfrei ausgeruesteten fasermaterialien

Also Published As

Publication number Publication date
EP0160872A2 (fr) 1985-11-13
DE3416693A1 (de) 1985-11-07
EP0160872A3 (en) 1987-05-20
JPS60239579A (ja) 1985-11-28
DE3566007D1 (en) 1988-12-08
US4629468A (en) 1986-12-16

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