DE918634C - Process for the production of dye-fast dyeings on acetyl cellulose and linear polyamides or polyurethanes - Google Patents
Process for the production of dye-fast dyeings on acetyl cellulose and linear polyamides or polyurethanesInfo
- Publication number
- DE918634C DE918634C DEN5086A DEN0005086A DE918634C DE 918634 C DE918634 C DE 918634C DE N5086 A DEN5086 A DE N5086A DE N0005086 A DEN0005086 A DE N0005086A DE 918634 C DE918634 C DE 918634C
- Authority
- DE
- Germany
- Prior art keywords
- brown
- carboxylic acid
- amino
- same
- polyurethanes
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
- C09B29/22—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of 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
- D06P1/02—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 azo dyes
- D06P1/12—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 azo dyes prepared in situ
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung überfärbeechter Färbungen auf Acetylcellulose sowie linearen Polyamiden oder Polyurethanen Zur Einarbeitung von Effektfäden in Stoffe aus Wolle und Wolle-Zellwolle-Mischungen lassen sich zweckmäßig solche aus Acetylcellulose oder aus linearen Polyamiden bzw. Polyurethanen verwenden. Die Auswahl der hierfür benötigten Farbstoffe, die den bei diesem Artikel üblichen ÜberfärbeprozeB ohne eine wesentliche Änderung von Farbton oder Farbstärke überstehen, ist sehr gering. So bestand auch bisher noch ein Mangel an geeigneten braunen Farbtönen, und zwar an solchen Produkten, die mit einer ausreichenden Überfärbeechtheit zugleich eine gute Lichtechtheit vereinen.Process for the production of dye-fast dyeings on acetyl cellulose as well as linear polyamides or polyurethanes For incorporating fancy threads into Fabrics made of wool and wool-rayon blends can expediently be left out Use acetyl cellulose or linear polyamides or polyurethanes. The selection the dyes required for this, which the over-dyeing process usual for this article survive without a significant change in hue or color strength is very small amount. So up to now there was still a lack of suitable brown shades, namely on products that are sufficiently fast to overdye at the same time combine good lightfastness.
Es wurde nun gefunden, daB man braune Färbungen mit guten Gesamtechtheiten und sehr guter Überfärbeechtheit auf Acetylcellulose sowie linearen Polyamiden oder Polyurethanen erhält, wenn man dieses Material, unter der Widerstandsfähigkeit der Faser angepaßten Bedingungen, mit Aminen von der allgemeinen Zusammensetzung: worin X für eine der Gruppen - S OZ - oder - C 0 -steht, der Benzolrest a noch weiter durch Alkyl-, Alkoxy-, Aryloxygruppen oder Halogenatome substituiert sein kann, R1 und R2 Wasserstoff, Alkyl-, Aralkyl-, Arylreste oder hydroaromatische Reste bedeuten, mit der Maßgabe jedoch, daß beide dann keine Wasserstoffatome sein sollen, wenn die Gruppe in o-Stellung zur Aminogruppe steht, worin ferner R1 und R2, wenn sie gleichzeitig Alkylreste darstellen, auch noch unter Bildung eines heterocyclischen Ringes miteinander verbunden sein können, und den Alkaliverbindungen von Arylamiden der 2-Oxycarbazol-3-carbonsäure, der 3-Oxydiphenylenoxyd-2-carbonsäure oder der 3-Oxydiphenylensulfid-2-carbonsäure in wässeriger Lösung behandelt, auf der Faser diazotiert und anschließend in einem heißen Bad fertig entwickelt.It has now been found that brown dyeings with good overall fastness properties and very good over-dyeing fastness on acetyl cellulose and linear polyamides or polyurethanes are obtained if this material is mixed with amines of the general composition under conditions adapted to the resistance of the fiber: where X is one of the groups - S OZ - or - C 0 -, the benzene radical a can be further substituted by alkyl, alkoxy, aryloxy groups or halogen atoms, R1 and R2 are hydrogen, alkyl, aralkyl, aryl or hydroaromatic radicals Mean radicals, with the proviso, however, that both should not be hydrogen atoms when the group is in the o-position to the amino group, in which R1 and R2, if they simultaneously represent alkyl radicals, can also be linked to one another to form a heterocyclic ring, and the alkali compounds of arylamides of 2-oxycarbazole-3-carboxylic acid, of 3-oxydiphenylene oxide -2-carboxylic acid or 3-oxydiphenylene sulfide-2-carboxylic acid treated in aqueous solution, diazotized on the fiber and then fully developed in a hot bath.
Zweckmäßig verwendet man solche Arylamide der Oxycarbonsäuren, deren Alkaliverbindungen sich durch eine besonders gute Löslichkeit in schwach alkalischem wässerigem Medium auszeichnen, so daß die Menge an freiem Ätzalkali, das unter Umständen auf die Faser wirken könnte, möglichst gering gehalten werden kann.It is useful to use such arylamides of the oxycarboxylic acids, their Alkali compounds are characterized by a particularly good solubility in weakly alkaline aqueous medium, so that the amount of free caustic alkali that may could act on the fiber, can be kept as low as possible.
Farbstoffe aus Diazokomponenten und Azokomponenten von der Art, wie sie hier Verwendung finden, sind zwar bereits Gegenstand verschiedener Patentschriften, wie z. B. der Patentschriften 7o3 iig, 704 032, 708 017 und 741357, doch wird in diesen Veröffentlichungen lediglich die Herstellung der Farbstoffe in Pulverform und ihre Verwendung zum Färben von Lacken, Filmen, Kautschuk beschrieben. Es finden sich nirgends Hinweise darauf, daß die Farbstoffkomponenten auf die Acetylcellulose- oder Polyamid- bzw. Polyurethanfaser aufgebracht und dort zu Färbungen entwickelt werden können.Dyestuffs from diazo components and azo components of the type as they are used here are already the subject of various patents, such as. B. the patents 7o3 iig, 704 032, 708 017 and 741357, but only the preparation of the dyes in powder form and their use for coloring paints, films, rubber is described in these publications. Nowhere are there any indications that the dye components can be applied to the acetylcellulose or polyamide or polyurethane fibers and developed there into colorations.
Auch war keineswegs vorauszusehen, daß die Sulfamid- oder Carbonsäureamidgruppen der Farbstoffe der starken Beanspruchung, wie sie der Überfärbeprozeß darstellt, in so guter Weise standhalten.It was also by no means foreseeable that the sulfamide or carboxamide groups the dyes of heavy use, as represented by the over-dyeing process, withstand in such a good way.
Beispiel i i kg Acetatkunstseidengarn wird etwa i bis i1/2 Stunden bei 75° in einem Bade behandelt, das man durch Eintragen einer heißen Lösung von 2o g des Natriumsalzes von i-(2'-Oxycarbazol-3'-carboylamino)-4-chlorbenzol und 2o,6 g i-Amino-2, 5-dimethoxybenzol-4-sulfonsäure-di-n-butylamid in i5o ccm Diäthanolamin und 18 ccm Wasser in eine Mischung aus 301 heißem Wasser, go g eines Kondensationsproduktes aus höhermolekularen Fettsäuren und Eiweißabbauprodukten, 30 ccm 25°/oigem Ammoniak und 6oo g Kochsalz erhält.Example ii kg of acetate rayon yarn is treated for about i to i1 / 2 hours at 75 ° in a bath which is obtained by adding a hot solution of 20 g of the sodium salt of i- (2'-oxycarbazole-3'-carboylamino) -4-chlorobenzene and 2o, 6 g of i-amino-2, 5-dimethoxybenzene-4-sulfonic acid-di-n-butylamide in 150 cc of diethanolamine and 18 cc of water in a mixture of 301 hot water, go g of a condensation product of higher molecular weight fatty acids and protein degradation products, 30 cc of 25% ammonia and 600 g of table salt are obtained.
Anschließend diazotiert man während etwa 1/2 Stunde in der Kälte in einem Bad, das 30 g Natriumnitrit und 150 ccm Salzsäure von 2o° B6 in 301 Wasser enthält, und entwickelt dann die Färbung durch eine Behandlung mit 30 g Oleylmethyltaurin,12o g Natriumacetat und 3 ccm Ammorxiak 25°/"ig in 301 Wasser von 6o°, erwärmt langsam auf 8o° und spült nach 1/,1 Stunde. Man erhält ein Dunkelbraun von guter Überfärbeechtheit. Beispiel 2 i kg Acetatkunstseidengarn wird i 1/2 Stunden bei 75' in einem Bade behandelt, das in 301 Wasser von 75' go g eines Kondensationsproduktes aus höhermolekularen Fettsäuren und Eiweißabbauprodukten, 30 ccm 25°/oiges Ammoniak, 6oo g Kochsalz enthält und mit einer heißen Lösung von 2o g des Natriumsalzes von i-(2'-Oxycarbazol-3'-carboylamino)-4-chlorbenzol und 14 g i-Amino-2-methoxybenzol-5-carbonsäurepiperidid in 150 ccm Monoäthanolamin, und 18 ccm Wasser versetzt wird.It is then diazotized for about 1/2 hour in the cold in a bath containing 30 g of sodium nitrite and 150 cc of hydrochloric acid at 20 ° B6 in 301 water, and the color is then developed by treatment with 30 g of oleylmethyltaurine, 12o g of sodium acetate and 3 cc Ammorxiak 25 ° / "ig in water of 301 ° 6o, slowly heated to 8o ° and rinsed out after 1/1 h. example 2 to give a dark brown good cross-dyeing. Acetatkunstseidengarn kg i i 1/2 hours at 75 ' treated in a bath that contains 75 g of a condensation product of higher molecular weight fatty acids and protein degradation products, 30 ccm of 25% ammonia, 600 g of common salt in water and a hot solution of 20 g of the sodium salt of i- (2 '-Oxycarbazole-3'-carboylamino) -4-chlorobenzene and 14 g of i-amino-2-methoxybenzene-5-carboxylic acid piperidide in 150 cc of monoethanolamine and 18 cc of water are added.
Anschließend diazotiert man während 1/2 Stunde in der Kälte in einem frischen Bad, das 30 g Natriumnitrit und 150 ccm Salzsäure von 2o° B6 in 301 Wasser enthält, und entwickelt dann die Färbung durch Behandeln mit 30 g Oleylmethyltaurin und i2o g Natriumacetat in 301 Wasser von 6o°.It is then diazotized for 1/2 hour in the cold in a fresh bath containing 30 g of sodium nitrite and 150 cc of hydrochloric acid at 20 ° B6 in 301 water, and the color is then developed by treating with 30 g of oleylmethyltaurine and 12o g of sodium acetate in 301 60 ° water.
Man steigert die Temperatur auf 8o°, behandelt etwa 1/2 Stunde lang und spült, wobei ein Rotbraun von guter Überfärbeechtheit erhalten wird. Beispiel 3 Behandelt man i kg Polyamidfasergarn nach den Angaben des Beispiels i, jedoch unter Verwendung von i-Amino-2, 4-dimethoxybenzol-5-sulfonsäure-din-butylamid an Stelle von i-Amino-2, 5-dimetboxybenzol-4-sulfonsäure-di-n-butylamid, so erhält man eine Rotbraunfärbung von guter Überfärbeechtheit.The temperature is raised to 80 °, treated for about 1/2 hour and rinses, a reddish brown of good color fastness being obtained. example 3 If i kg of polyamide fiber yarn is treated as described in example i, however using i-amino-2,4-dimethoxybenzene-5-sulfonic acid din-butylamide Place of i-amino-2, 5-dimetboxybenzene-4-sulfonic acid-di-n-butylamide, so obtained a red-brown dyeing of good over-dyeing fastness.
Die folgende Zusammenstellung enthält eine Anzahl von weiteren, nach
vorliegendem Verfahren verwendbaren Komponenten sowie die Farbtöne der auf der Faser
entwickelten Monoazofarbstoffe, die gleichfalls gute Echtheitseigenschaften besitzen:
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEN5086A DE918634C (en) | 1952-02-14 | 1952-02-14 | Process for the production of dye-fast dyeings on acetyl cellulose and linear polyamides or polyurethanes |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEN5086A DE918634C (en) | 1952-02-14 | 1952-02-14 | Process for the production of dye-fast dyeings on acetyl cellulose and linear polyamides or polyurethanes |
Publications (1)
Publication Number | Publication Date |
---|---|
DE918634C true DE918634C (en) | 1954-09-30 |
Family
ID=7338498
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEN5086A Expired DE918634C (en) | 1952-02-14 | 1952-02-14 | Process for the production of dye-fast dyeings on acetyl cellulose and linear polyamides or polyurethanes |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE918634C (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1049020B (en) * | 1956-07-11 | 1959-01-22 | Bayer Ag | Process for the preparation of water-insoluble azo dyes |
DE1051241B (en) * | 1956-07-14 | 1959-02-26 | Hoechst Ag | Process for the production of brown, insoluble azo dyes on molded articles made of aromatic polyesters |
DE1267660B (en) * | 1961-10-18 | 1968-05-09 | Hoechst Ag | Process for the continuous production of brown, water-insoluble azo dyes on fabrics made from vegetable fibers |
DE1268102B (en) * | 1960-02-04 | 1968-05-16 | Hoechst Ag | Process for the production of metal-containing, water-insoluble azo dyes on the fiber |
WO2014147182A3 (en) * | 2013-03-20 | 2014-11-13 | Bayer Pharma Aktiengesellschaft | Substituted n-biphenyl-3-acetylamino-benzamides and n-[3-(acetylamino)phenyl]-biphenyl-carboxamides and their use as inhibitors of the wnt signalling pathway |
-
1952
- 1952-02-14 DE DEN5086A patent/DE918634C/en not_active Expired
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1049020B (en) * | 1956-07-11 | 1959-01-22 | Bayer Ag | Process for the preparation of water-insoluble azo dyes |
DE1051241B (en) * | 1956-07-14 | 1959-02-26 | Hoechst Ag | Process for the production of brown, insoluble azo dyes on molded articles made of aromatic polyesters |
DE1268102B (en) * | 1960-02-04 | 1968-05-16 | Hoechst Ag | Process for the production of metal-containing, water-insoluble azo dyes on the fiber |
DE1267660B (en) * | 1961-10-18 | 1968-05-09 | Hoechst Ag | Process for the continuous production of brown, water-insoluble azo dyes on fabrics made from vegetable fibers |
WO2014147182A3 (en) * | 2013-03-20 | 2014-11-13 | Bayer Pharma Aktiengesellschaft | Substituted n-biphenyl-3-acetylamino-benzamides and n-[3-(acetylamino)phenyl]-biphenyl-carboxamides and their use as inhibitors of the wnt signalling pathway |
CN105579457A (en) * | 2013-03-20 | 2016-05-11 | 拜耳制药股份公司 | Substituted N-biphenyl-3-acetylamino-benzamides and N-[3-(acetylamino)phenyl]-biphenyl-carboxamides and their use as inhibitors of the WNT signalling pathway |
JP2016521259A (en) * | 2013-03-20 | 2016-07-21 | バイエル・ファルマ・アクティエンゲゼルシャフト | Substituted N-biphenyl-3-acetylamino-benzamide and N- [3- (acetylamino) phenyl] -biphenyl-carboxamide and their use as inhibitors of the Wnt signaling pathway |
CN105579457B (en) * | 2013-03-20 | 2017-08-04 | 拜耳制药股份公司 | The substituted acetyl-amino benzamide of N biphenyl 3 and N [3 (acetyl-amino) phenyl] dibenzoyl amine and its it is used as WNT signal pathway inhibitor purposes |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE1544446B2 (en) | Water-insoluble monoazo dyes free from sulfonic and carboxylic acid groups and process for their preparation | |
DE2142412C3 (en) | Disazo compounds, their production and use for dyeing and printing polyamide or polyurethane fiber materials | |
DE918634C (en) | Process for the production of dye-fast dyeings on acetyl cellulose and linear polyamides or polyurethanes | |
DE942325C (en) | Process for the production of dye-fast dyeings on acetyl cellulose and linear polyamides or polyurethanes | |
DE904886C (en) | Process for the production of color-fast colors on acetyl cellulose as well as linear polyamides and polyurethanes | |
DE957506C (en) | Process for the production of cobalt-containing azo dyes | |
DE897991C (en) | Process for the production of color-fast colors on acetyl cellulose as well as linear polyamides and polyurethanes | |
DE896039C (en) | Process for the production of color-fast colors on acetyl cellulose as well as linear polyamides and polyurethanes | |
DE917991C (en) | Process for the preparation of new trisazo dyes | |
DE1239421B (en) | Process for the production of azo dyes | |
DE906569C (en) | Process for the production of dye-fast dyeings on acetyl cellulose and linear polyamides or polyurethanes | |
DE914246C (en) | Process for the production of dye-fast colorings on acetyl cellulose and linear polyamides or polyurethanes | |
DE849880C (en) | Process for the production of new sulfonic acid group-free monoazo dyes of the pyrazolone series | |
DE937524C (en) | Process for the production of dye-fast dyeings on acetyl cellulose and linear polyamides or polyurethanes | |
DE1222187B (en) | Process for the preparation of water-insoluble disazo dyes | |
DE935964C (en) | Process for the production of dye-fast coloring on fiber material made of acetyl cellulose as well as linear polyamides or polyurethanes | |
DE2433232C3 (en) | Dyeing preparations for the production of water-insoluble azo dyes on the fiber | |
DE395917C (en) | Process for the preparation of water-insoluble azo dyes | |
DE955881C (en) | Process for the production of cobalt-containing azo dyes | |
DE666478C (en) | Process for the production of azo dyes | |
DE1147701B (en) | Process for the preparation of metal complex compounds of monoazo dyes | |
DE578065C (en) | Process for the production of water-insoluble azo dyes | |
DE845636C (en) | Process for the production of real colors on fibrous materials | |
DE556474C (en) | Process for the preparation of azo dyes | |
DE266356C (en) |