DE657117C - Process for improving the properties of dyeings with substantive dyes containing sulfonic acid or carboxylic acid groups on cellulose fibers - Google Patents

Process for improving the properties of dyeings with substantive dyes containing sulfonic acid or carboxylic acid groups on cellulose fibers

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Publication number
DE657117C
DE657117C DEI55142D DEI0055142D DE657117C DE 657117 C DE657117 C DE 657117C DE I55142 D DEI55142 D DE I55142D DE I0055142 D DEI0055142 D DE I0055142D DE 657117 C DE657117 C DE 657117C
Authority
DE
Germany
Prior art keywords
dyeings
properties
sulfonic acid
improving
carboxylic acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
DEI55142D
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German (de)
Inventor
Dr Otto Bayer
Dr Siegfried Petersen
Dr Karl Taube
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.)
IG Farbenindustrie AG
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IG Farbenindustrie AG
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Filing date
Publication date
Priority to DENDAT304780D priority Critical patent/DE304780C/de
Priority to DE1916300536D priority patent/DE300536C/de
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DEI55142D priority patent/DE657117C/en
Priority to GB17579/36A priority patent/GB478953A/en
Priority to NL82496A priority patent/NL46452C/xx
Priority to US143726A priority patent/US2190848A/en
Priority to FR822252D priority patent/FR822252A/en
Priority to FR822282D priority patent/FR822282A/en
Application granted granted Critical
Publication of DE657117C publication Critical patent/DE657117C/en
Priority to BE478953D priority patent/BE478953A/xx
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04Polysiloxanes
    • C08G77/06Preparatory processes
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B23MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
    • B23KSOLDERING OR UNSOLDERING; WELDING; CLADDING OR PLATING BY SOLDERING OR WELDING; CUTTING BY APPLYING HEAT LOCALLY, e.g. FLAME CUTTING; WORKING BY LASER BEAM
    • B23K11/00Resistance welding; Severing by resistance heating
    • B23K11/08Seam welding not restricted to one of the preceding subgroups
    • B23K11/087Seam welding not restricted to one of the preceding subgroups for rectilinear seams
    • B23K11/0873Seam welding not restricted to one of the preceding subgroups for rectilinear seams of the longitudinal seam of tubes
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • 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
    • D06P1/00General 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
    • D06P1/44General 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
    • D06P1/64General 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
    • D06P1/642Compounds containing nitrogen
    • D06P1/6426Heterocyclic compounds
    • 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
    • D06P1/00General 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
    • D06P1/44General 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
    • D06P1/64General 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
    • D06P1/642Compounds containing nitrogen
    • D06P1/645Aliphatic, araliphatic or cycloaliphatic compounds containing amino groups
    • 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
    • D06P1/00General 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
    • D06P1/44General 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
    • D06P1/64General 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
    • D06P1/642Compounds containing nitrogen
    • D06P1/649Compounds containing carbonamide, thiocarbonamide or guanyl groups
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916Natural fiber dyeing
    • Y10S8/918Cellulose textile

Description

Verfahren zur Verbesserung der Eigenschaften von Färbungen mit Substantiven, Sulfonsäure-oder Carbonsäuregruppen enthaltenden Farbstoffen auf Cellulosefasern Es ist bekannt, daß man auf Cellulosefasern Sulfonsäure- oder Carbonsäuregruppen enthaltende Farbstoffe mit Basen, deren Salzen oder quartären Aminoniuinverbindungen derart in Wechselwirkung bringen kann, daß färberische Änderungen, Animälisierung und Verbesserung der Naßechtheiten erzielt werden. Dies wird z. B. durch Nachbehandeln der gefärbten Ware mit den Basen oder auch durch Vorbehandeln der ungefärbten Ware mit den basischen Verbindungen und Cberfärben mit direkt ziehenden oder sauren Farbstoffen erreicht.Process for improving the properties of coloring with nouns, Dyes containing sulfonic acid or carboxylic acid groups on cellulose fibers It is known that sulfonic acid or carboxylic acid groups are found on cellulose fibers containing dyes with bases, their salts or quaternary amino compounds can interact in such a way that coloring changes, animation and improvement of the wet fastness properties can be achieved. This is z. B. by post-treatment the dyed goods with the bases or by pretreating the undyed goods with the basic compounds and dyeing with direct or acidic dyes achieved.

Es wurde nun gefunden, daß man die Naßechtheiten und zum Teil auch die Lichtechtheit durch Nachbehandeln von Färbungen mit sauren, wasserlöslichen substantiven Farbstoffen auf Cellulosefasern mit Lösungen von Basen, die Metall komplex gebunden enthalten und noch mit Säuren Salze zu bilden vermögen, in stärkerem Maße als nach den bekannten Verfahren verbessern kann. In einigen Fällen wird über diese Echtheitsverbesserungen hinaus eine erhebliche Vertiefung oder Änderung des Farbtons, die von Wert sein kann, erzielt.It has now been found that the wet fastness properties and in part also the lightfastness by post-treating dyeings with acidic, water-soluble ones substantive dyes on cellulose fibers with solutions of bases, the metal Contain complex bound and still be able to form salts with acids, in stronger Can improve dimensions than by the known methods. In some cases it will be over These authenticity improvements also involve a significant deepening or modification of the Hue that can be of value.

Besonders geeignete Basen mit komplex gebundenem Metall sind beispielsweise: Die Metallkomplexv erbindungen von Biguanid, 8 Aminochinolin, 8-Aninochinaldin, Äthylendiamin, TfiiohaLrnstoff, o-Phenanthrolin und 2, 2'-Dipyridyl, -wobei die basischen komplexen Gruppen auch Bestandteil farbiger Verbindungen sein können.Particularly suitable bases with complexed metal are, for example: The metal complex compounds of biguanide, 8-aminoquinoline, 8-aninochinaldine, Ethylenediamine, TfiiohaLrnstoff, o-phenanthroline and 2,2'-dipyridyl, - where the basic complex groups can also be part of colored compounds.

Das Verfahren -wird in der Weise ausgeführt, daß die gefärbten Fasern mit einer gegebenenfalls schwach sauren oder alkalischen, wässerigen Lösung der Metallkomplexverbindungen der Basen behandelt werden. Man kann aber auch so verfahren, daß die .L\Tetallkomplexverbindungen der Basen bei der Behandlung der Färbungen in dem Behandlungsbade entstehen. Beispiel i Baumwollgarn wird mit 61,f. Direkttiefschwarz EW extra (vgl. Schultz, Farbstofftabellen, ;. Auflage, Nr. 671) in der üblichen Weise gefärbt, gespült und mit einer wässerigen Lösung des Sulfats von i, i'-Dimethylbiguanidkupfer bei 30° C % Stunde nachbehandelt, abermals gespült und getrocknet.The process - is performed in such a manner that the colored fibers are treated with an optionally slightly acid or alkaline, aqueous solution of the metal complex compounds of the bases. But you can also proceed in such a way that the .L \ Tetallkomplexverbindungen of the bases arise in the treatment of the dyeings in the treatment bath. Example i Cotton yarn is marked with 61, f. Direct deep black EW extra (cf. Schultz, Dye Tables,;. Edition, No. 671) dyed, rinsed and post-treated with an aqueous solution of the sulfate of i, i'-dimethylbiguanide copper at 30 ° C for 1 hour, rinsed and again dried.

Die Wasserechtheit und Waschechtheit der so behandelten Färbungen ist im Vergleich zu den Naßechtheiten der unbehandelten Färbung wesentlich verbessert.The waterfastness and washfastness of the dyeings treated in this way is in comparison on the wet fastness properties of the untreated dye much improved.

Unterzieht man eine 2prozentige Färbung von Kongorot (vgl. Schultz, a. a. O., Nr. 369);e derselben Nachbehandlung, so wird der Farn ton etwas blaustichiger, und die Wasser- Waschechtheit wird gleichzeitig erhöht. D' Nachbehandlung kann auch warm erfolgen. Das Sulfat des i, i'-Dimethylbiguanidkupfers läßt sich herstellen aus Kupfersulfat, einer wässerigen Lösung von Dirnethylamin und Dicvandiamid bei erhöhter Temperatur unter Druck. Die Substanz löst sich in Wasser unter Zusatz von Natriumchlorid oder einem anderen Neutralsalz, gegebenenfalls unter- Mitverwendung von wenig Natriumcarbonat.Subject to a 2 percent staining from Congo red (cf. Schultz, op. cit., no. 369); e the same aftertreatment, so will the fern tone a little more bluish, and the water Washfastness is increased at the same time. D ' Post-treatment can also be done warm. The sulfate of i, i'-dimethylbiguanide copper can be prepared from copper sulfate, an aqueous solution of dimethylamine and dicvandiamide at elevated temperature under pressure. The substance dissolves in water with the addition of sodium chloride or another neutral salt, possibly with the use of a little sodium carbonate.

Beispiel 2 Baumwolle wird in der üblichen Weise mit 2 % des aus der Patentschrift 204 212" Beispiel 5, bekannten Farbstoffs gefärbt und mit einer@Lösung des Sulfats von i-Monoäthylbiguanidkupfer 1/2 Stunde bei 30° C nachbehandelt. Die Färbung zeigt eine gute Wasserechtheit. Das Nachbehandlungsmittel 'jtknd seine Lösung werden entsprechend den gaben in Beispiel i hergestellt. Zü ähnlichen Ergebnissen gelangt man bei Anwendung der Salze des Biguanidkupfers, des i-Monomethylbiguanidkupfers, des i, i'-Diäthylbiguanidkupfers oder ähnlich zusammengesetzter Verbindungen.Example 2 Cotton is dyed in the usual way with 2% of the dye known from patent specification 204 212 "Example 5 and aftertreated with a solution of the sulfate of i-monoethylbiguanide copper for 1/2 hour at 30 ° C. The coloration is good The aftertreatment agent 'jtknd his solution will be according to the were produced in example i. Similar results are obtained from Application of biguanide copper salts, of i-monomethyl biguanide copper, of i, i'-diethyl biguanide copper or compounds of similar composition.

Beispiel 3 Wenn man Baumwollfärbungen von Direkttiefschwarz EW extra mit der Lösung des Komplexsalzes aus i Mol. Kupferchlorür und 3 Mol. Thioharnstoff in üblicher Weise nachbehandelt, so wird die Wasserechtheit erhöht. Beispiel 4 Die wässerige Lösung des Kupferkomplexes der Verbindung folgender Zusammensetzung wird zur 1lTachbehandlung einer 2prozentigen Färbung von Diaminreinblau :2F (vgl. S c h u 1 t z , a. a. O., 2#Tr. 5 i (5) auf Baumwolle verwendet. Durch 1/2stündige Nachbehandlung, die auch in essigsaurer oder bicarbonatalkalischer Lösung erfolgen kann, wird der Farbton der unbehandelten Färbung wesentlich nach Grün verschoben. Die nachbehandelte Färbung zeichnet sich durch gute Wasser-, Wasch- und Lichtechtheit aus.Example 3 If cotton dyeings of direct deep black EW extra are post-treated in the usual way with the solution of the complex salt of 1 mol. Copper chloride and 3 mol. Thiourea, the water fastness is increased. Example 4 The aqueous solution of the copper complex of the compound of the following composition is used for the 1l after-treatment of a 2 percent coloration of pure diamine blue: 2F (cf. S chu 1 tz, loc. cit., 2 # Tr. 5 i (5)) on cotton. By 1/2-hour after-treatment, which can also be done in acetic acid or bicarbonate-alkaline solution , the hue of the untreated dyeing is shifted significantly towards green.The aftertreated dyeing is characterized by good water, wash and lightfastness.

Zu ähnlich verbesserter Wasser- und Waschechtheit gelangt man beim Nachbehandeln von Färbungen mit Kongorot .oder Direkttiefschwarz EW extra auf Baumwolle.A similarly improved water and wash fastness is achieved with Post-treatment of dyeings with Congo red or direct deep black EW extra on cotton.

Die obengenannte Verbindung gewinnt man, wenn man i Mol. Cyanürchlorid nacheinander mit je i 1M1. i-Aniinobenzol-3-triinetliylainmoniumclilorid und 5-Ainino-S-oxychinolin umsetzt.The abovementioned compound is obtained if one mole of cyanuric chloride one after the other with i 1M1 each. i-Aniinobenzol-3-triinetliylainmoniumclilorid and 5-Ainino-S-oxyquinoline implements.

Beispiel 5 Man färbt Baumwolle mit 21/, des Azofarbstoffs, den man durch Kuppeln von i Mol. Diazobenzol und i Mol. dianotierter 2-Aminonaphtlialin-6-sulfosäure mit dem Harnstoff der 2-Amino-S-oxynaplithalin-7-sulfonsäure erhält. Die scharlachrote Färbung wird nach dem Spülen mit einer wässerigen Lösung der Komplexverbindung aus - Kupfersulfat und 8-Aniino-2-methylchinolin (lierstellbar durch Einrühren einer alkoholischen Lösung von 8-Ainino-2-metliylchinolin in eine wässerige Kupfer stilfatlösung) '/., Stunde bei 30° C behandelt. Sie wird dabei dunkelbraun und ist gut licht-und waschecht.Example 5 Cotton is dyed with 21 /, the azo dye that is used by coupling 1 mole of diazobenzene and 1 mole of dianotated 2-aminonaphthlialine-6-sulfonic acid obtained with the urea of 2-amino-S-oxynaplithalin-7-sulfonic acid. The scarlet one Coloring will come off after rinsing with an aqueous solution of the complex compound - Copper sulfate and 8-aniino-2-methylquinoline (can be added by stirring in a alcoholic solution of 8-ainino-2-methylquinoline in an aqueous copper stilfate solution) Treated '/., Hour at 30 ° C. It becomes dark brown and is good light and washable.

Werden Färbungen von Diamingrün B (vgl. S c h u 1 t z, a: a. O., Nr. 668) auf Baumwolle in der in Absatz i beschriebenen Weise behandelt, so werden sie gleichfalls im Farbton wesentlich verändert und waschechter. Beispiel 6 Eine 2prozentige Färbung von Diaminreinblau 21# auf Baumwolle behandelt man -1/,Stunde in einem Bade, das den Kupferkomplex, darstellbar aus Kupfersulfat und 8-Aminochindlin, gelöst enthält. Die Färbung wird etwas trüber und waschechter. , Beispiel 7 Man färbt Baumwolle mit 7 °;o des Disazofarbstoffs, den man durch Kuppeln von dianotierter 5- Amino-2-oxybenzol-i-carbonsä ure mit i -Aminonaplitlialin, Weiterdiazotieren und Kuppeln mit 2-Amino-S-oxynaphthalin-6-sulfonsäure erhält, und behandelt diese Färbung bei 30° C mit der wässerigen Lösung von 4., 5-Diazaphenanthrenkupferchlorid (aus 4, j-Diazaphenaiithren-o-Phenanthr olin und Kupferchlorid). Die Färbung wird grünstichiger und in ihrer Waschechtheit verbessert.If dyeings of diamond green B (cf. S chu 1 tz, a: op. Cit., No. 668) on cotton are treated in the manner described in paragraph i, they are also significantly changed in color and are more washable. EXAMPLE 6 A 2 percent staining of pure diamine blue 21 # on cotton is treated for -1 /, hour in a bath which contains the copper complex, which can be prepared from copper sulfate and 8-amino cindline, in solution. The color becomes a little cloudy and more washable. EXAMPLE 7 Cotton is dyed with 7% of the disazo dye obtained by coupling dianotated 5-amino-2-oxybenzene-i-carboxylic acid with i-aminonaplitlialin, further diazotization and coupling with 2-amino-S-oxynaphthalene-6 sulfonic acid, and treats this coloration at 30 ° C with the aqueous solution of 4, 5-diazaphenanthrene copper chloride (from 4, j-diazaphenaiithren-o-phenanthroline and copper chloride). The dyeing becomes greener and its fastness to washing is improved.

An Stelle des o-Plienanthrolins kann das durch Nitrieren dieser Base gewonnene Nitrophenanthrolin oder das daraus durch Reduktion erhältliche Amin oder das Umsetzungsprodukt von 2, 3-Diaminonaphthalin mit 2 Mol. Glycerin (nach S k r a u p) in Form der Kupferkomplexverbindung zur Nachbehandlung verwendet werden. Beispiel 8 Baumwollfärbungen von Diamingrün B werden in ihrer Wasser- und Waschechtheit verbessert, wenn man sie mit Lösungen der 1oniplexsaize aus Kupferchlorid mit i oder 2M01. 2, 2'-Dipy ridyl nachbehandelt.Instead of o-plienanthroline, this can be done by nitrating this base obtained nitrophenanthroline or the amine obtainable therefrom by reduction or the reaction product of 2,3-diaminonaphthalene with 2 mol. glycerol (according to S k r a u p) can be used for aftertreatment in the form of the copper complex compound. Example 8 Diamond green B cotton dyeings are water and wash fastness improved if they are treated with solutions of the 1oniplexsaize of copper chloride with i or 2M01. 2, 2'-Dipyridyl aftertreated.

Komplexe Eisensalze dieser Art verbessern die Wasserechtheit von Färbungen ebenfalls. Beispiel 9 Baumwolle, die mit Direkttiefschwarz EW extra gefärbt ist, wird mit einer Lösung des Kupferkomplexsalzes von N, N'-Tetrainethyli, 2-diamiiiobenzol nachbehandelt. Derartige Lösungen sind z. B. erhältlich durch Zusammengeben von i 11o1. Base und i Mol. Kupferacetat in Alkohol und Verdünnen -dieser gegebenenfalls filtrierten alkoholischen Lösung mit Wasser. Die NaBechtheiten der nachbehandelten Färbung werden verbessert.Complex iron salts of this type improve the waterfastness of dyeings Likewise. Example 9 Cotton, which is extra dyed with direct deep black EW, is with a solution of the copper complex salt of N, N'-Tetrainethyli, 2-diamiiiobenzol post-treated. Such solutions are z. B. obtainable by combining i 11o1. Base and 1 mole of copper acetate in alcohol and diluting this if necessary filtered alcoholic solution with water. The aftertreatment of the after-treated Coloring are improved.

Ähnlich wirkt z. B. eine Lösung der Kupferkomplexverbindung von i-Monomethylamino-2-aminobenzol.Similarly acts z. B. a solution of the copper complex compound of i-monomethylamino-2-aminobenzene.

Claims (2)

PATrNTANSPRÜCHE: i. Verfahren zur Verbesserung der Eigenschaften von Färbungen mit substantiven, Sulfonsäure- und Carbonsäure-Jgruppen enthaltenden Farbstoffen auf Cellulosefaserh, dadurch gekennzeichnet, daß man die gefärbte Ware mit Lösungen der mit Säuren noch Salze bildenden komplexen Metallverbindungen organischer Basen behandelt. CLAIMS: i. Process for improving the properties of Dyeings with substantive dyes containing sulfonic acid and carboxylic acid groups on cellulose fiber, characterized in that the dyed goods are mixed with solutions the complex metal compounds of organic bases that form salts with acids treated. 2. Abänderung des Verfahrens nach Anspruch i, dadurch gekennzeichnet, daP man Behandlungsbäder verwendet, welche die Basen und die zur Metallkornplexbildung mit den Basen befähigten Metallverbindungen enthalten.2. Modification of the method according to claim i, characterized in that because treatment baths are used, which contain the bases and those for the formation of metal complexes Contain metal compounds capable of the bases.
DEI55142D 1936-05-31 1936-05-31 Process for improving the properties of dyeings with substantive dyes containing sulfonic acid or carboxylic acid groups on cellulose fibers Expired DE657117C (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
DENDAT304780D DE304780C (en) 1936-05-31
DE1916300536D DE300536C (en) 1936-05-31 1916-11-22
DEI55142D DE657117C (en) 1936-05-31 1936-05-31 Process for improving the properties of dyeings with substantive dyes containing sulfonic acid or carboxylic acid groups on cellulose fibers
GB17579/36A GB478953A (en) 1936-05-31 1936-06-24 Process for the manufacture on the fibre of transformation products of dyestuffs containing sulphonic acid or carboxylic acid groups
NL82496A NL46452C (en) 1936-05-31 1937-05-14
US143726A US2190848A (en) 1936-05-31 1937-05-20 Dyeings
FR822252D FR822252A (en) 1936-05-31 1937-05-26 Method for improving dyes on textile fibers and the like
FR822282D FR822282A (en) 1936-05-31 1937-05-27 Advanced valve faucet
BE478953D BE478953A (en) 1936-05-31 1947-12-30

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEI55142D DE657117C (en) 1936-05-31 1936-05-31 Process for improving the properties of dyeings with substantive dyes containing sulfonic acid or carboxylic acid groups on cellulose fibers
GB17579/36A GB478953A (en) 1936-05-31 1936-06-24 Process for the manufacture on the fibre of transformation products of dyestuffs containing sulphonic acid or carboxylic acid groups

Publications (1)

Publication Number Publication Date
DE657117C true DE657117C (en) 1938-02-28

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DENDAT304780D Expired DE304780C (en) 1936-05-31
DE1916300536D Expired DE300536C (en) 1936-05-31 1916-11-22
DEI55142D Expired DE657117C (en) 1936-05-31 1936-05-31 Process for improving the properties of dyeings with substantive dyes containing sulfonic acid or carboxylic acid groups on cellulose fibers

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Application Number Title Priority Date Filing Date
DENDAT304780D Expired DE304780C (en) 1936-05-31
DE1916300536D Expired DE300536C (en) 1936-05-31 1916-11-22

Country Status (6)

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US (1) US2190848A (en)
BE (1) BE478953A (en)
DE (3) DE300536C (en)
FR (2) FR822252A (en)
GB (1) GB478953A (en)
NL (1) NL46452C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE954686C (en) * 1953-08-17 1956-12-20 Bayer Ag Agent for improving the fastness properties of dyeings of substantive dyes on cellulose fibers

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3325242A (en) * 1967-06-13 Process for dyeing and printing with reactive dyestuffs
US2649354A (en) * 1947-12-01 1953-08-18 Sandoz Ltd Process for improving fastiness properties of direct dyestuffs
US2576241A (en) * 1950-04-03 1951-11-27 Dan River Mills Inc Dye fixing product and process and treating of textiles therewith
DE968041C (en) * 1951-05-10 1958-01-09 Bayer Ag Process for the production of copper-containing, higher molecular weight, basic condensation products
GB869660A (en) * 1958-01-15 1961-06-07 Ici Ltd Treatment of cellulosic materials
GB927772A (en) * 1959-09-24 1963-06-06 Ici Ltd New textile colouring process
BE621442A (en) * 1961-08-17

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE954686C (en) * 1953-08-17 1956-12-20 Bayer Ag Agent for improving the fastness properties of dyeings of substantive dyes on cellulose fibers

Also Published As

Publication number Publication date
NL46452C (en) 1939-08-15
BE478953A (en) 1948-01-31
DE304780C (en) 1918-04-10
FR822252A (en) 1937-12-24
FR822282A (en) 1937-12-24
GB478953A (en) 1938-01-24
US2190848A (en) 1940-02-20
DE300536C (en) 1917-09-26

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