DE939206C - Process for dyeing or printing structures made from cellulose esters - Google Patents

Process for dyeing or printing structures made from cellulose esters

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Publication number
DE939206C
DE939206C DEB22061A DEB0022061A DE939206C DE 939206 C DE939206 C DE 939206C DE B22061 A DEB22061 A DE B22061A DE B0022061 A DEB0022061 A DE B0022061A DE 939206 C DE939206 C DE 939206C
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sulfonic acid
dyeing
cellulose esters
structures made
acid
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BASF SE
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BASF SE
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    • 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
    • D06P1/64—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 low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/645—Aliphatic, araliphatic or cycloaliphatic compounds containing amino groups
    • 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
    • D06P1/62—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 low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic groups
    • D06P1/628—Compounds containing nitrogen
    • 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
    • D06P1/64—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 low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • 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
    • D06P1/64—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 low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/6421—Compounds containing nitrile groups
    • 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
    • D06P1/64—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 low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/6426—Heterocyclic compounds
    • 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
    • D06P1/64—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 low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
    • D06P1/6492—(Thio)urethanes; (Di)(thio)carbamic acid derivatives; Thiuramdisulfide
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/40—Cellulose acetate
    • D06P3/401—Cellulose acetate using acid dyes
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/40—Cellulose acetate
    • D06P3/405—Cellulose acetate using metallisable or mordant dyes

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Hydrogenated Pyridines (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

Es wurde gefunden, daß man Gebilde aus Celluloseestern, wie Fäden, Bänder, Fasern, Flocken, Vorgespinste, Gewebe und Gewirke, färben kann, wenn man sie mit geringen Mengen von organischen Aminen, insbesondere cycloaliphatischen Aminen mit mindestens 3 C-Atomen, die außer einer Aminogruppe noch mindestens eine Nitril-, Ester-, Oxy- oder Carbonylgruppe enthalten, gegebenenfalls in Form ihrer Aldehyd-Bisulfit-Verbindungen oder ihrer Salze mit organischen oder anorganischen Säuren, behandelt und gleichzeitig oder nachträglich mit solchen Farbstoffen färbt, die Sulfonsäure- oder SuIfonamidgruppen und bzw. oder komplex gebundenes Metall enthalten.It has been found that structures made of cellulose esters, such as threads, tapes, fibers, flakes, roving, Woven and knitted fabrics, if they are dyed with small amounts of organic amines, in particular cycloaliphatic amines with at least 3 carbon atoms other than one amino group contain at least one nitrile, ester, oxy or carbonyl group, optionally in their form Aldehyde bisulfite compounds or their salts with organic or inorganic acids and at the same time or afterwards colors with such dyes, the sulfonic acid or sulfonamide groups and / or contain metal bound in complexes.

Geeignete Amine sind z. B. Dimethylaminopropionitril, N-Phenyl-N-methylaminopropionitril, Pyrrolidinoisobuttersäurenitril, Hexamethylen - diamino dipropionitril, Hexahydrotoluidinopropionitril, das Umsetzungsprodukt aus 4, 4'-Diamino-dicyclohexylmethan mit Acrylnitril, Dimethylaminopropionsäuremethyl- oder -äthylester, ferner das Tetramethyldiaminobenzophenon, das Tetramethyldiaminodicyclohexylketon oder das N, N'-Bis-(Oxyäthyl)-4,4'-diaminodicyclohexylmethan. Suitable amines are e.g. B. dimethylaminopropionitrile, N-phenyl-N-methylaminopropionitrile, pyrrolidinoisobutyronitrile, Hexamethylene - diamino dipropionitrile, hexahydrotoluidinopropionitrile, the Reaction product of 4,4'-diamino-dicyclohexylmethane with acrylonitrile, dimethylaminopropionic acid methyl or ethyl ester, also tetramethyldiaminobenzophenone, tetramethyldiaminodicyclohexyl ketone or N, N'-bis (oxyethyl) -4,4'-diaminodicyclohexylmethane.

Die basischen Verbindungen können in Form von wässerigen Dispersionen oder in Form ihrer wasserlöslichen Formaldehyd-Bisulfit-Verbindungen oder ihrer Salze mit organischen oder anorganischen Säuren, z. B. mit Ameisen-, Essig- oder Weinsäure, mit Salz- oder Schwefelsäure oder mit organischen Sulfonsäuren angewandt werden. Entweder behandelt man die Gebilde aus Celluloseestern mit Lösungen oder Dispersionen der Stoffe vor und färbt dann, oder manThe basic compounds can be in the form of aqueous dispersions or in the form of their water-soluble Formaldehyde bisulfite compounds or their salts with organic or inorganic Acids, e.g. B. with formic, acetic or tartaric acid, with hydrochloric or sulfuric acid or with organic Sulphonic acids are applied. Either the structures made of cellulose esters are treated with solutions or Dispersions of the fabrics before and then dyed, or one

setzt die genannten Verbindungen dem Färbebad zu. Im letzteren Fall erweist es sich als zweckmäßig, die zum Aufbringen des Farbstoffs notwendige organische oder anorganische Säure dem Färbebad nicht vollständig von vornherein, sondern allmählich in Anteilen zuzusetzen.adds the compounds mentioned to the dyebath. In the latter case, it proves to be expedient to use the organic or inorganic acid required to apply the dye is not completely in the dyebath from the start, but gradually to be added in proportions.

Geeignete SuIfonsäure- oder SuIf onamidgruppen und bzw. oder komplex gebundenes Metall enthaltende Farbstoffe sind z. B. i-Amino-4-(m-cyanphenyl)-ο amino anthrachinon - 2 - sulf onsäure, i, 4 - Diamino anthrachinon-2-sulfonsäure, der Azofarbstoff aus diazotiertem 4 - Methyl -1 - aminobenzol - 3 - sulf onsäure anilid und 1, 4-Naphtholsulfonsäure, das gelbe Kondensationsprodukt aus 2, 4-Dinitrochlorbenzol und 4-Aminodiphenylaminsulfonsäure, die komplexe Kupferverbindung des Azofarbstoffe aus diazotiertem 2-Aminophenol-4-sulfonsäureanilid und 2-Oxynaphthalin, die komplexe Kobaltverbindung des Azofarbstoffe aus diazotiertem 2-Aminophenol-4-sulfonsäureamid und 2-Oxynaphthalin oder die komplexe Chromverbindung des Azofarbstoffs aus diazotiertem 4-Chlor-2-aminophenol und 2-Oxynaphthalin-6-sulfonsäure. Die aufgezählten Farbstoffe sind nur als Beispiele aus verschiedenen Farbstoffklassen genannt, wobei -die Erfindung weder auf diese Farbstoffe noch auf die Farbstoffklassen beschränkt ist.Suitable sulfonic acid or sulfonamide groups and or dyes containing complexed metal are z. B. i-Amino-4- (m-cyanophenyl) -ο amino anthraquinone - 2 - sulfonic acid, i, 4 - diamino anthraquinone-2-sulfonic acid, the azo dye from diazotized 4 - methyl -1 - aminobenzene - 3 - sulfonic acid anilide and 1,4-naphtholsulfonic acid, the yellow condensation product from 2,4-dinitrochlorobenzene and 4-aminodiphenylamine sulfonic acid, the complex copper compound of azo dyes from diazotized 2-aminophenol-4-sulfonic acid anilide and 2-oxynaphthalene, the complex cobalt compound of the azo dye from diazotized 2-aminophenol-4-sulfonic acid amide and 2-oxynaphthalene or the complex chromium compound of the azo dye from diazotized 4-chloro-2-aminophenol and 2-oxynaphthalene-6-sulfonic acid. The dyes listed are only given as examples called different classes of dyes, the invention neither on these dyes nor on the Dye classes is limited.

Das Verfahren kann auch kontinuierlich durchgeführt werden.
Es ist zwar bekannt, daß man aus Celluloseestern bestehende Gebilde nach Aufbringen kationaktiver Substanzen mit sulfonsäuregruppenhaltigen Farbstoffen färben kann, doch befriedigen diese Färbungen hinsichtlich ihrer Echtheitseigenschaften, insbesondere ihrer Reibechtheit, in keiner Weise, da sie nur Oberflächenfärbungen sind. Das vorliegende Verfahren gestattet es, Celluloseester mit sauren Farbstoffen bzw. mit komplex gebundenes Metall enthaltenden Farbstoffen echt zu färben.The process can also be carried out continuously.
Although it is known that structures consisting of cellulose esters can be colored with dyes containing sulfonic acid groups after application of cationic substances, these dyeings are in no way satisfactory in terms of their fastness properties, in particular their rubbing fastness, since they are only surface dyeings. The present process makes it possible to dye cellulose esters with acidic dyes or with dyes containing complexed metal.

Beispiel 1example 1

100 g eines Acetatreyongewebes werden- in 21 Wasser, in dem 4 g der Formaldehyd-Bisuhit-Verbindung des Umsetzungsproduktes aus 4, 4'-Diaminodicyclohexylmethan und Acrylnitril gelöst wurden, x/2 Stunde lang bei 75 bis 8o° behandelt. Das Gewebe wird dann gespült und in einem frischen Bad, das in 21 Wasser 2 g des Farbstoffes i-Amino-4-(m-cyanphenyl)-aminoanthrachinon-2-sulfonsäure und 2 g o,60/0ige Schwefelsäure enthält, 1Z2 Stunde bei 75 bis 80° gefärbt. Das gefärbte Gewebe wird wie üblich fertiggestellt.100 g of an Acetatreyonewebes are - in 21 water, in which 4 g of the formaldehyde bisuhitol compound of the reaction product of 4,4'-diaminodicyclohexylmethane and acrylonitrile were dissolved, treated for x / 2 hours at 75 to 80 °. The fabric is then rinsed and dye i-amino-4- (m-cyanophenyl) -aminoanthraquinone-2-sulfonic acid in a fresh bath containing 21 g of water in 2 and contains 2 go, 6 0/0 by weight sulfuric acid, 1 Z Stained for 2 hours at 75 to 80 °. The dyed fabric is finished as usual.

Man erhält tiefblaue Färbungen, die eine sehr gute Lichtechtheit und gute bis sehr gute Naßechtheitseigenschaften haben.Deep blue dyeings are obtained which have very good lightfastness and good to very good wet fastness properties to have.

Beispiel 2Example 2

100 g eines Acetatreyongewebes werden in 21 Wasser, das 2 g N-(Spiro-Cyclohexyläthylenimino)-propionsäurenitril in emulgierter Form enthält, 20 Minuten bei 75 bis 8o° behandelt. Nach kurzem Spülen färbt man in einem Färbebad, das in 21 Wasser 2 g des· Farbstoffes 1, 4-Diaminoanthrachinon-2-sulfonsäure und 2 g 85°/oige Ameisensäure enthält, V2 Stunde bei 75 bis 8o°.100 g of an Acetatreyonewebes are in 21 water, which contains 2 g of N- (Spiro-Cyclohexyläthylenimino) propionic acid nitrile in emulsified form, treated for 20 minutes at 75 to 80 °. After a brief rinse is dyed in a dyebath containing in 21 water 2 g of the dye · 1, 4-diaminoanthraquinone-2-sulfonic acid and contains 2 g of 85 ° / o formic acid, V 2 hour at 75 to 8o °.

Man erhält tiefviolette Färbungen mit guten Echtheitseigenschaften. Deep purple dyeings with good fastness properties are obtained.

Beispiel 3Example 3

io'o g eines Acetatreyongewebes werden in 31 Wasser, das 6 g des Umsetzungsproduktes von Spirocyclohexyl-äthylenimin mit Chlorameisensäure-äthylester enthält, 30 Minuten bei 75 bis 85° bewegt. Nach kurzem Spülen färbt man in einem Bade, das in 3 1 Wasser 2 g des Azofarbstoffes aus diazotiertem 4-Methyl-i-aminobenzol-2-sulfonsäureanilid und 1, 4-Naphtholsulfonsäure sowie 4g o,6°/0ige Schwefelsäure enthält. Die resultierende rote Färbung ist hervorragend echt.10'o g of Acetatreyonewebes are in 31 water, which contains 6 g of the reaction product of spirocyclohexyl-ethylenimine with ethyl chloroformate, agitated for 30 minutes at 75 to 85 °. After a brief rinse in a dyeing bath that g in 3 1 water 2 of the azo dyestuff obtained from diazotised 4-methyl-i-aminobenzene-2-sulfonsäureanilid and 1, 4-naphtholsulfonic acid and containing 4g o, 6 ° / 0 sulfuric acid. The resulting red coloration is superbly real.

Beispiel 4Example 4

100 g Acetatreyongarn werden in 21 Wasser, in dem 2 g Tetramethyldiaminodicyclohexylketon und 2 g des Kondensationsprodukts aus 2,4-Dinitrochlorbenzol und 4-Aminodiphenylaminsulfonsäure gelöst sind, 20 Minuten bei 75 bis 85 ° bewegt. Dann setzt man dem Färbebad insgesamt 3 g 85%ige Ameisensäure in vier Anteilen zu, indessen man 30 Minuten bei 75 bis 85 ° weiterfärbt. Die entstehenden gelben Färbungen sind von guter Echtheit.100 g Acetatreyonarn are in 21 water, in the 2 g of tetramethyldiaminodicyclohexyl ketone and 2 g of the condensation product from 2,4-dinitrochlorobenzene and 4-aminodiphenylamine sulfonic acid are dissolved, agitated for 20 minutes at 75 to 85 °. Then sets a total of 3 g of 85% formic acid in four portions are added to the dyebath, during which time it is 30 minutes continues to color at 75 to 85 °. The resulting yellow dyeings are of good fastness.

Beispiel 5Example 5

100 g eines Acetatreyongewebes werden mit einer aus 75 g der Formaldehyd-Bisulfit-Verbindung des Umsetzungsproduktes aus 4, 4'-Diaminodicyclohexylmethan und Acrylnitril, 400 g British Gummi und 525 g Wasser bestehenden Druckpaste bedruckt, getrocknet und dann 15 Minuten im Matterplatt bei 102° gedämpft und schließlich gespült. Das bedruckte Gewebe wird hierauf in einem Bad, das in 2 1 Wasser 2 g i-Amino^-^-cyanphenylJ-aminoanthrachinon-2-sulfonsäure und 2 g konzentrierte Schwefelsäure enthält, 1^ Stunde bei 75 bis 8o° gefärbt und wie üblich fertiggestellt. Man erhält tiefblaue, scharf stehende Drucke mit guten Echtheitseigenschaften.100 g of an Acetatreyonewebes are printed with a 75 g of the formaldehyde bisulfite compound of the reaction product of 4,4'-diaminodicyclohexylmethane and acrylonitrile, 400 g of British rubber and 525 g of water existing printing paste, dried and then 15 minutes in the Matterplatt at 102 ° steamed and finally rinsed. The printed fabric is then dyed in a bath containing 2 g of i-amino ^ - ^ - cyanphenylJ-aminoanthraquinone-2-sulfonic acid and 2 g of concentrated sulfuric acid in 2 liters of water and dyed for 1 ^ hour at 75 to 80 ° and finished as usual . Deep blue, sharp prints with good fastness properties are obtained.

Beispiel 6Example 6

100 g eines Acetatreyongewebes werden in einer Emulsion von 2 g N-(Spiro-Cyclohexyläthylenimino)-propionsäurenitril in 21 Wasser 20 Minuten bei 75 bis 8o° behandelt, gespült und getrocknet. Das so vorbehandelte Gewebe wird anschließend mit einer aus 40 g i-Amino^-phenylaminoanthrachinon^-sulfonsäure, 10 g Essigsäure 3o%ig, 400 g British Gummi100 g of an Acetatreyongewebes are in an emulsion of 2 g of N- (Spiro-Cyclohexyläthylenimino) propionic acid nitrile treated in 21 water for 20 minutes at 75 to 80 °, rinsed and dried. That pretreated Tissue is then treated with one of 40 g of i-amino ^ -phenylaminoanthraquinone ^ -sulfonic acid, 10 g acetic acid 3o%, 400 g British gum

<i 550 S Wasser bestehenden Druckpaste bedruckt, 20 Minuten gedämpft und dann gespült. Man erhält scharfstehende tiefblaue Drucke mit ausgezeichneten Echtheitseigenschaften.<i 550 S water-based printing paste, steamed for 20 minutes and then rinsed. Sharp deep blue prints with excellent fastness properties are obtained.

Beispiel 7Example 7

Acetatreyongewebe wird mit einer aus 60 g des aus 1*5 4-Amino-3-sulfo-i)8-naphthalindicarbonsäureanhydridAcetatreyonewebe is with one of 60 g of 1 * 5 4-amino-3-sulfo-i ) 8-naphthalenedicarboxylic anhydride

undToluidin erhältlichen Farbstoffs, ioo gAmmoniumrhodanid, 350 g British Gummi, 390 g Wasser und 100 g der Formaldehyd-Bisulfit-Verbindung des Umsetzungsproduktes aus 4,4'-Diaminodicyclohexylmethan und Acrylnitril bestehenden Druckpaste bedruckt und dann 20 Minuten ohne Druck bei etwa 102° gedämpft und anschließend gespült.and toluidine available dye, 100 g ammonium rhodanide, 350 g of British rubber, 390 g of water and 100 g of the formaldehyde-bisulfite compound of the reaction product printed from 4,4'-diaminodicyclohexylmethane and acrylonitrile existing printing paste and then steamed for 20 minutes without pressure at about 102 ° and then rinsed.

Man erhält scharfstehende, brillante und floureszierende grünstichiggelbe Drucke von sehr guten Echtheitseigenschaften.Sharp, brilliant and fluorescent ones are obtained greenish yellow prints with very good fastness properties.

Beispiel 8Example 8

Man behandelt 100 g eines Acetatseidengewebes 1Z2 Stunde bei 75 bis 80° in 2 1 eines wässerigen Bades, das 4 g eines Gemisches der Formaldehyd-Bisulfit-Verbindungen von 4, 4'-Diaminodicyclohexylmethan-N, N'-dipropionitril und ß-(N-Cyclohexylamino)-propibnitril (im ungefähren Molverhältnis 2:1) enthält. Nach dem Spülen färbt man das behandelte Gewebe 3/4 Stunden bei 75 bis 8o° in 21 eines wässerigen Bades, das 2 g i-Amino-4-(meta-cyanphenyl)-aminoanthrachinon-2-sulfonsäure und 2 g a.6°/0ige Schwefelsäure enthält. Nach der üblichen Fertigstellung erhält man eine sehr legale, lichtechte tiefblaue Färbung von sehr guten Naßechtheiten.Treating 100 g of a Acetatseidengewebes 1 Z 2 hour at 75 ° to 80 ° in 2 1 of an aqueous bath comprising 4 g of a mixture of the formaldehyde-bisulfite compounds of 4, 4'-diamino-N, N'-dipropionitril and .beta. (N-Cyclohexylamino) propibonitrile (in an approximate molar ratio of 2: 1). After purging dyeing the treated fabric 3/4 hour at 75 to 8o ° in 21 of an aqueous bath containing 2 g i-amino-4- (meta-cyanophenyl) -aminoanthraquinone-2-sulfonic acid and 2 g a.6 ° / Contains 0 sulfuric acid. After the usual finishing, a very legal, lightfast deep blue dyeing with very good wet fastness properties is obtained.

Beispiel 9Example 9

Man bringt 100 g Acetatseidengarn in 21 eines wässerigen Bades, das 3 g eines Einwirkungsproduktes von Natriumhydrogensulfit und Formaldehyd auf ein Gemisch aus etwa 2 Molekülen 4, 4'-Diaminodicyclohexylrnethan-N, N'-dipropionitril und 1 Molekül |3-(N-[Methyl-cyclohexyl]-amino)-propionitril sowie g des Azofarbstoffe aus diazotiertem i-Amino-4-methylbenzol-2-sulfonsäureanilid und i-Oxynaphthalin-4-sulfonsäure enthält, und bewegt, das Garn x/2 Stunde bei 75 bis 80° in dem Bade. Dann setzt man dem Bade unter weiterem Bewegen des Färbegutes in Abständen von je 10 Minuten viermal je 0,5 g 96°/oige Schwefelsäure zu und setzt das Färben fort, bis der Farbstoff vollständig aufgezogen ist. Die erhaltenen leuchtendroten Färbungen sind sehr egal und gut naß- und lichtecht. ~100 g of acetate silk yarn are placed in an aqueous bath containing 3 g of an action product of sodium hydrogen sulfite and formaldehyde on a mixture of about 2 molecules of 4,4'-diaminodicyclohexylmethane-N, N'-dipropionitrile and 1 molecule of | 3- (N- [ Methyl-cyclohexyl] -amino) propionitrile and g of the azo dyes from diazotized i-amino-4-methylbenzene-2-sulfonic acid anilide and i-oxynaphthalene-4-sulfonic acid, and moves the yarn x / 2 hours at 75 to 80 ° in the bath. Then added to the bath with continued movement of the material to be dyed at intervals of 10 minutes four times per 0.5 g of 96 ° / o strength sulfuric acid and continuing the dyeing, is fully wound until the dye. The bright red dyeings obtained are very irrelevant and have good wet and lightfastness. ~

Claims (1)

PATENTANSPRUCH:PATENT CLAIM: Verfahren zum Färben oder Bedrucken von Gebilden aus Celluloseestern, dadurch gekennzeichnet, daß man die Gebilde mit geringen Mengen von organischen Aminen, insbesondere cycloaliphatischen Aminen mit mindestens 3 C-Atomen, die außer einer Aminogruppe noch mindestens eine Nitril-, Ester-, Oxy- oder Carbonylgruppe enthalten, gegebenenfalls in Form ihrer Aldehyd-Bisulfit-Verbindungen oder ihrer Salze mit organischen oder anorganischen Säuren, behandelt und gleichzeitig oder nachträglich mit solchen Farbstoffen färbt, die Sulfonsäure- oder Sulfonamidgruppen und bzw. oder komplexgebundenes Metall enthalten.Process for dyeing or printing structures made of cellulose esters, characterized in that that the structures with small amounts of organic amines, especially cycloaliphatic Amines with at least 3 carbon atoms which, in addition to one amino group, have at least one Contain nitrile, ester, oxy or carbonyl groups, optionally in the form of their aldehyde-bisulfite compounds or their salts with organic or inorganic acids, treated and simultaneously or subsequently with such dyes colors, the sulfonic acid or sulfonamide groups and / or complex-bound metal contain. Angezogene Druckschriften:
Französische Patentschriften Nr. 745 039, 835 993.Referred publications:
French patents nos. 745 039, 835 993. 6 509 647 2.566 509 647 2.56
DEB22061A 1952-04-03 1952-09-17 Process for dyeing or printing structures made from cellulose esters Expired DE939206C (en)

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DEB22061A DE939206C (en) 1952-04-03 1952-09-17 Process for dyeing or printing structures made from cellulose esters

Applications Claiming Priority (2)

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DEB19839A DE925042C (en) 1952-04-03 1952-04-03 Process for improving the exhaust gas fastness of colored cellulose esters and ethers
DEB22061A DE939206C (en) 1952-04-03 1952-09-17 Process for dyeing or printing structures made from cellulose esters

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DEB19839A Expired DE925042C (en) 1952-04-03 1952-04-03 Process for improving the exhaust gas fastness of colored cellulose esters and ethers
DEB22061A Expired DE939206C (en) 1952-04-03 1952-09-17 Process for dyeing or printing structures made from cellulose esters
DEB31568A Expired DE953428C (en) 1952-04-03 1954-06-26 Process for dyeing or printing structures made from cellulose esters
DEB32636A Expired DE960001C (en) 1952-04-03 1954-09-18 Process for dyeing or printing structures made from cellulose esters

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DEB32636A Expired DE960001C (en) 1952-04-03 1954-09-18 Process for dyeing or printing structures made from cellulose esters

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US (1) US2813773A (en)
DE (4) DE925042C (en)
FR (3) FR1077680A (en)
GB (2) GB725353A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1131640B (en) * 1958-11-17 1962-06-20 Ciba Geigy Process for dyeing structures made of cellulose triacetate

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2888314A (en) * 1955-01-27 1959-05-26 Rohm & Haas Textile material and inhibition of acid-fading dyes thereon
DE1119817B (en) * 1959-03-25 1961-12-21 Basf Ag Process for dyeing and printing structures that consist entirely or in part of synthetic, linear, fiber-forming polyesters
US8198395B2 (en) * 2007-02-07 2012-06-12 Air Products And Chemicals, Inc. Alkylated aminopropylated ethylenediamines and uses thereof
US7993751B2 (en) * 2007-02-07 2011-08-09 Air Products And Chemicals, Inc. Alkylated aminopropylated methylene-di-(cyclohexylamine) and uses thereof
US8318309B2 (en) * 2007-02-07 2012-11-27 Air Products And Chemicals, Inc. Benzylated aminopropylated alkylenediamines and uses thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR745039A (en) * 1933-05-01
FR835993A (en) * 1938-03-31 1939-01-06 Improvements in the treatment of textiles and similar products

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US2017119A (en) * 1931-02-11 1935-10-15 Celanese Corp Treatment of textile and other materials
US2529935A (en) * 1947-10-15 1950-11-14 Gen Aniline & Film Corp Acid-fading inhibition using certain 1, 4-diaryl piperazines
US2539212A (en) * 1948-11-05 1951-01-23 Gen Aniline & Film Corp Gas fading inhibitors for cellulose derivative dyes

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR745039A (en) * 1933-05-01
FR835993A (en) * 1938-03-31 1939-01-06 Improvements in the treatment of textiles and similar products

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1131640B (en) * 1958-11-17 1962-06-20 Ciba Geigy Process for dyeing structures made of cellulose triacetate

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FR1087963A (en) 1955-03-02
US2813773A (en) 1957-11-19
DE953428C (en) 1956-11-29
DE960001C (en) 1957-03-14
FR1077680A (en) 1954-11-10
GB725353A (en) 1955-03-02
GB742029A (en) 1955-12-14
FR68702E (en) 1958-06-09
DE925042C (en) 1955-03-10

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