CH122256A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH122256A CH122256A CH122256DA CH122256A CH 122256 A CH122256 A CH 122256A CH 122256D A CH122256D A CH 122256DA CH 122256 A CH122256 A CH 122256A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- azo dye
- parts
- dye
- forms
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000004922 lacquer Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- OCISOSJGBCQHHN-UHFFFAOYSA-N 3-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC(O)=CC2=C1 OCISOSJGBCQHHN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 235000015250 liver sausages Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 125000005000 thioaryl group Chemical group 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Darstellung eines Azofarbstoffes. Es wurde gefunden, dass man wertvolle neue Azofarbstoffe erhält, wenn man Diazo- verbindungen von Aminen der allgemeinen Formel:
EMI0001.0007
worin die X's Wasserstoff oder einen ein wertigen Substituenten, das eine Y eine Gruppe SO,-Alkyl, SO,- Aralkyl, SO--Aryl oder SOz-N < , das andere Y Halogen, Alkyl, Aralkyl, Aryl, Oxalkyl, Oxaralkyl oder Ox- aryl, Thioalkyl, Thioaralkyl oder Thioaryl bedeuten können,
mit 2.3-Oxynaphtoesäure- aryliden kuppelt.
Man erhält so Farbstoffe, die mit Sub straten vermischt, wertvolle Lacke ergeben und deren Färbungen, wenn die Farbstoffe auf der Faser erzeugt werden, neben einer klaren Nüance eine besonders gute Beuch- echtheit aufweisen. Im Falle die obiger Formel entsprechen den Aminoarylsulfone oder Aminoarylsul- fonsäureamide in einem Aralkyl- oder zwei ten Arylrest noch eine weitere Amiuogruppe enthalten,
können beide Aminogruppen dia- zotiert und die so entstandenen Diazoverbin- dungen auf zwei Moleküle eines 2. 3-Oxy - naphtoesäurearylids zur Einwirkung kom men.
Falls ein Di-2. 3-oxynaphtoylarylendi- amin zur Verwendung kommt, reagiert das selbe mit zwei Molekülen der Diazoverbindung eines Monoamins der obigen Formel bezw. mit einem Molekül der Tetrazoverbindun;7 eines Diamins der zuletzt erwähnten .Art.
Vorliegendes Patent bezieht sich nun auf die Darstellung eines neuen Azofarbstoffes, welcher dadurch entsteht, dass man die Diazo- verbindung von 2-Aminotolyl-4-phenylsulfon der Formel:
EMI0001.0060
mit ? . d-Oxynaplitoyl-a-naphtylamin kom biniert.
Getrocknet bildet der Farbstoff ein blau stichig rotes Pulver, das in -Wasser unlöslich ist. Mit den gebräuchlichen Substraten ge- ini,cht, bildet er einen blaustichig roten Lack und färbt, auf Baumwolle hergestellt, die selbe in den gleichen Tönen von guter Lielit- echtheit und Beuchechtheit. <I>Beispiel:</I> 7,4 Teile 2 Aminotolyl-4-plieny lsulfon werden mit 16 Teilen Salzsäure (:
d=1,160) fein angerieben, mit 50 Teilen Wasser und Liy gut vermischt und mit 2,1 Teilen Natriumnitrit, gelöst in 15 Teilen Wasser, dianotiert. Zu dieser Lösung- lässt man eine filtrierte Lösung von 9,5 Teilen 2. ä-Oxy- naphtoyl-a-naphtylamin in 8,4 Teilen Na tronlauge<B>(36-</B> Be), 1 Teil Türkischrotöl, <B>150</B> Teilen Wasser und 8,7 Teilen Natrium .. cetat kristallisiert zulaufen. Nach einigen Stunden ist die Kupplung beendet. Man er hält den Farbstoff als blaustichig rote Pate.
Process for the preparation of an azo dye. It has been found that valuable new azo dyes are obtained if diazo compounds of amines of the general formula:
EMI0001.0007
wherein the X's are hydrogen or a monovalent substituent, one Y is a group SO, -alkyl, SO, -aralkyl, SO-aryl or SOz-N <, the other Y is halogen, alkyl, aralkyl, aryl, oxalkyl, oxaralkyl or Oxaryl, thioalkyl, thioaralkyl or thioaryl,
couples with 2,3-oxynaphthoic acid arylides.
In this way, dyes are obtained which, when mixed with substrates, give valuable varnishes and, when the dyes are produced on the fiber, the colorations of which, in addition to a clear shade, have particularly good appearance fastness. In the case of the above formula, the aminoarylsulphones or aminoarylsulphonic acid amides contain another amino group in an aralkyl or second aryl radical,
Both amino groups can be diazotized and the diazo compounds thus formed can act on two molecules of a 2,3-oxynaphthoic acid arylide.
If a Tue-2. 3-oxynaphtoylarylenediamine is used, the same reacts with two molecules of the diazo compound of a monoamine of the above formula, respectively. with a molecule of the tetrazo compound; 7 of a diamine of the last-mentioned type.
The present patent now relates to the preparation of a new azo dye, which arises from the fact that the diazo compound of 2-aminotolyl-4-phenylsulfone of the formula:
EMI0001.0060
With ? . d-Oxynaplitoyl-a-naphthylamine combined.
When dried, the dye forms a blue-tinged red powder that is insoluble in water. In harmony with the common substrates, it forms a bluish-tinged red lacquer and, produced on cotton, dyes the same in the same shades of good lightfastness and touchfastness. <I> Example: </I> 7.4 parts of 2 aminotolyl-4-plieny lsulfon are mixed with 16 parts of hydrochloric acid (:
d = 1.160) finely rubbed, mixed well with 50 parts of water and Liy and dianotized with 2.1 parts of sodium nitrite dissolved in 15 parts of water. A filtered solution of 9.5 parts of 2-oxynaphtoyl-a-naphthylamine in 8.4 parts of sodium hydroxide solution (36 Be), 1 part of Turkish red oil is added to this solution B> 150 parts of water and 8.7 parts of sodium .. acetate run in crystallized form. The coupling is complete after a few hours. The dye is thought of as a bluish red pate.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE122256X | 1925-05-28 | ||
| DE80625X | 1925-06-08 | ||
| CH120522T | 1926-05-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH122256A true CH122256A (en) | 1927-09-01 |
Family
ID=27176740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH122256D CH122256A (en) | 1925-05-28 | 1926-05-27 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH122256A (en) |
-
1926
- 1926-05-27 CH CH122256D patent/CH122256A/en unknown
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