DE541072C - Process for dyeing or printing cellulose esters or ethers - Google Patents
Process for dyeing or printing cellulose esters or ethersInfo
- Publication number
- DE541072C DE541072C DEI34857D DEI0034857D DE541072C DE 541072 C DE541072 C DE 541072C DE I34857 D DEI34857 D DE I34857D DE I0034857 D DEI0034857 D DE I0034857D DE 541072 C DE541072 C DE 541072C
- Authority
- DE
- Germany
- Prior art keywords
- dyeing
- ethers
- cellulose esters
- printing cellulose
- printing
- 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
- 238000004043 dyeing Methods 0.000 title claims description 7
- 229920002678 cellulose Polymers 0.000 title claims description 4
- 229920003086 cellulose ether Polymers 0.000 title claims description 4
- 150000002170 ethers Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 230000008878 coupling Effects 0.000 claims description 7
- 238000010168 coupling process Methods 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 239000000987 azo dye Substances 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 235000015250 liver sausages Nutrition 0.000 claims 1
- XYSQXZCMOLNHOI-UHFFFAOYSA-N s-[2-[[4-(acetylsulfamoyl)phenyl]carbamoyl]phenyl] 5-pyridin-1-ium-1-ylpentanethioate;bromide Chemical compound [Br-].C1=CC(S(=O)(=O)NC(=O)C)=CC=C1NC(=O)C1=CC=CC=C1SC(=O)CCCC[N+]1=CC=CC=C1 XYSQXZCMOLNHOI-UHFFFAOYSA-N 0.000 claims 1
- 239000000975 dye Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- AIRRELHUAAZTTL-UHFFFAOYSA-N 3-nitrobenzenesulfonic acid;sodium Chemical compound [Na].OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 AIRRELHUAAZTTL-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
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
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zum Färben oder Bedrucken von Celluloseestern oder -äthern Es wurde gefunden, daß Azofarbstoffe, die erhältlich sind aus Diazoverbindungen, die keine Sulfonsäure- oder Carbonsäuregruppen enthalten, und 0xychinolonen, die am Stickstoff alkyliert sind, sich zum Färben oder Bedrucken von Acetatseide besonders gut eignen. Die neuen Produkte sind in Wasser unlöslich und zeigen zu den Celluloseestern und -äthern eine in vielen Fällen hervorragend gute Affinität.Process for dyeing or printing cellulose esters or ethers It has been found that azo dyes which are obtainable from diazo compounds, which do not contain sulfonic acid or carboxylic acid groups, and oxyquinolones which are alkylated on nitrogen, especially for dyeing or printing acetate silk well suited. The new products are insoluble in water and point towards the cellulose esters and ethers have an excellent affinity in many cases.
So stellen beispielsweise die Kupplungsprodukte aus den Diazoverbindungen von Anilin oder seinen Homologen mit N-i<lethyl-.l-oxy-2-chinolon Farbstoffe dar, die Acetatseide in wertvollen grünstichiggelben Tönen von ausgezeichneten Echtheitseigenschaften anfärben und auch für den Druck auf Acetatseide geeignet sind. Die Affinität ist gegenüber den bekannten, von Sulfo- und Carboxylgruppen freien Azofarbstoffen aus Dioxychinolin wesentlich gesteigert und ermöglicht es, bei Auswahl geeigneter Azokomponenten Färbungen von bisher besonders in grünstichiggelben Farbtönen urierreichter Echtheit zu erzielen.For example, make the coupling products from the diazo compounds of aniline or its homologues with N-i <lethyl-.l-oxy-2-quinolone dyes the acetate silk in valuable greenish yellow tones with excellent fastness properties dye and are also suitable for printing on acetate silk. The affinity is compared to the known azo dyes free of sulfo and carboxyl groups Dioxyquinoline increased significantly and made it possible with the selection of suitable azo components Dyeings of authenticity that were previously particularly rich in greenish-yellow shades to achieve.
Durch Anwendung geeignet substituierter Diazo- bzw. Kupplungskomponenten kann der Farbton der Verbindungen irt weiten Grenzen verändert werden. Beispiel i Der durch Kupplung von diamtiertem p-Chloranilin mit 6-Chlor-N-äthyl-4-oxy-2-chinolon hergestellte Farbstoff wird in einer der gewünschten Farbtiefe entsprechenden 'Menge (etwa o,i bis 2,o °/o, berechnet auf das Färbegut) in einem Seifenbade (2 bis 3 g Seife pro Liter) mit der zu färbenden Acetatseide (Flottenverhältnis etwa i : 30) 1 , bis i Stunde auf 6o bis 75 erwärmt. Man erhält sehr klare, grünstichiggelbe Färbungen von ausgezeichneten Echtheitseigenschaften.By using suitably substituted diazo or coupling components the color of the connections can be changed over a wide range. example i The coupling of diamted p-chloroaniline with 6-chloro-N-ethyl-4-oxy-2-quinolone produced dye is in an 'amount corresponding to the desired depth of color (about o, i to 2, o%, calculated on the dyed material) in a soap bath (2 to 3 g soap per liter) with the acetate silk to be dyed (liquor ratio about i: 30) 1, heated to 60 to 75 for an hour. Very clear, greenish-yellowish ones are obtained Dyeings with excellent fastness properties.
Man kann mit dem gleichen Ergebnis auch nach anderen, für in Wasser schwer oder unlösliche Farbstoffe üblichen Verfahren, beispielsweise im schwach sauren oder salzhaltigen Bade, färben. In Mischgeweben, beispielsweise mit Baumwolle, wird nur die Acetatseide angefärbt.One can with the same result after another, for in water poorly or insoluble dyes customary processes, for example in the weakly acidic or salty baths, color. In mixed fabrics, for example with cotton, only the acetate silk is dyed.
Verwendet man an Stelle des erwähnten Farbstoffes das Kupplungsprodukt-aus p-Amidodimethylanilin und N-methyl-4-oxy-2-chinolon, so erhält man sehr kräftige rotviolette Färbungen.If the coupling product is used instead of the dye mentioned p-Amidodimethylaniline and N-methyl-4-oxy-2-quinolone, very strong ones are obtained red-violet colorations.
Die Farbstoffe sind auch für den Druck auf Acetatseide geeignet. Beispiel 2 Der Farbstoff, der durch Kupplung von diazotiertem m-Nitranilin mit N-methvl-.l-oxy-2-chinolon entsteht, wird in der gewünschten Menge (etwa io bis 3o Teile) mit einer Paste von 5o Teilen Thiodiglykol, 75o Teilen Gummi= arabicumlösung i : i, 25 Teilen m-Nitrobenzolsulfonsaurem Natrium und etwa 125 Teilen Wasser vermischt, mit dieser Paste in üblicher Weise auf Acetatseide gedruckt und nach dem Trocknen 1'a Stunde ohne Druck gedämpft, dann schwäch geseift. Man erhält so gelbe Drucke mit sehr guten Echtheitseigenschaften.The dyes are also suitable for printing on acetate silk. example 2 The dye obtained by coupling diazotized m-nitroaniline with N-methvl-.l-oxy-2-quinolone arises, is in the desired amount (about 10 to 3o parts) with a paste of 50 parts of thiodiglycol, 75o parts of gum = arabic solution i: i, 25 parts of m-nitrobenzenesulfonic acid Sodium and about 125 parts of water mixed with this paste in the usual way way printed on acetate silk and steamed after drying for 1'a hour without pressure, then weakly soaped. Yellow prints with very good fastness properties are obtained in this way.
An Stelle der erwähnten Druckpaste können auch andere übliche Mischungen verwendet werden. Der Farbstoff eignet sich auch zum Färben von Acetatseide in hervorragender Weise.Instead of the printing paste mentioned, other customary mixtures can also be used be used. The dye is also ideal for dyeing acetate silk Way.
In ähnlicher Weise lassen sich die Farbstoffe verwenden, die als Diazokomponenten andere Substitutionsprodukte des Benzols oder seiner Homologen und als Kupplungskomponenten substituierte oder unsubstituierte N-alkyl-q.-oxya-chinolone enthalten.In a similar way, the dyes can be used as diazo components other substitution products of benzene or its homologues and as coupling components contain substituted or unsubstituted N-alkyl-q.-oxya-quinolones.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI34857D DE541072C (en) | 1928-07-06 | 1928-07-06 | Process for dyeing or printing cellulose esters or ethers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI34857D DE541072C (en) | 1928-07-06 | 1928-07-06 | Process for dyeing or printing cellulose esters or ethers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE541072C true DE541072C (en) | 1932-01-08 |
Family
ID=7188821
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI34857D Expired DE541072C (en) | 1928-07-06 | 1928-07-06 | Process for dyeing or printing cellulose esters or ethers |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE541072C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1244314B (en) * | 1960-07-30 | 1967-07-13 | Basf Ag | Process for the preparation of water-insoluble disazo dyes |
-
1928
- 1928-07-06 DE DEI34857D patent/DE541072C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1244314B (en) * | 1960-07-30 | 1967-07-13 | Basf Ag | Process for the preparation of water-insoluble disazo dyes |
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