DE1644056C - Monoazo dyes containing sulfonic acid groups - Google Patents
Monoazo dyes containing sulfonic acid groupsInfo
- Publication number
- DE1644056C DE1644056C DE1644056C DE 1644056 C DE1644056 C DE 1644056C DE 1644056 C DE1644056 C DE 1644056C
- Authority
- DE
- Germany
- Prior art keywords
- sulfonic acid
- acid groups
- containing sulfonic
- monoazo dyes
- dyes containing
- 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
- 239000000975 dye Substances 0.000 title claims description 11
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title claims description 3
- 125000000542 sulfonic acid group Chemical group 0.000 title claims description 3
- 238000004043 dyeing Methods 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000000463 material Substances 0.000 claims 1
- 239000004753 textile Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- WGLQHUKCXBXUDV-UHFFFAOYSA-N 3-aminophthalic acid Chemical compound NC1=CC=CC(C(O)=O)=C1C(O)=O WGLQHUKCXBXUDV-UHFFFAOYSA-N 0.000 description 1
- GQBONCZDJQXPLV-UHFFFAOYSA-N 4-aminoisoindole-1,3-dione Chemical class NC1=CC=CC2=C1C(=O)NC2=O GQBONCZDJQXPLV-UHFFFAOYSA-N 0.000 description 1
- OXSANYRLJHSQEP-UHFFFAOYSA-N 4-aminophthalic acid Chemical compound NC1=CC=C(C(O)=O)C(C(O)=O)=C1 OXSANYRLJHSQEP-UHFFFAOYSA-N 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- -1 sodium nitride Chemical class 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
Description
Hie Erfindung betrifft sulfonsäuregruppenhaltige Monoazofarbstoffe der ulluemeinen Formel IThe invention relates to monoazo dyes of the general formula I containing sulfonic acid groups
SO1HSO 1 H
— Ν- Ν
HOHO
NlI,NlI,
in der R Wasserstoff oder Methoxy bedeutet. Man erhält die neuen Farbstoffe, wenn man Diazoverbindüngen von Aminen der allgemeinen Formel IIin which R is hydrogen or methoxy. The new dyes are obtained by using diazo compounds of amines of the general formula II
NH,NH,
Rühren bei 3 his S C 30 Raumteile 23" »ige wäßrige Natriumnitriilösung langsam zulaufen. Während der Zugabe der Natriumnitritlösung setzt man 100 Teile Mis zu. Anschließend rührt man noch 2 Stunden bei 0 bis 5 C und stellt durch Zugabe einer 50"nigen Natriumacetatlösung einen pH-Wert von 4 ein. Zu der Dia/.olösung fügt man eine Lösung des Natriumsalzes von 24.3 Teilen 2-Amino-K-hydroxynaphtlv.ilin-6-sulfonsäure in 250 Raumteilen Wasser langsam zu. NachStirring at 3 to 30 parts by volume of 23 "strength aqueous Slowly run in the sodium nitride solution. 100 parts are added during the addition of the sodium nitrite solution Mis to. The mixture is then stirred for a further 2 hours at 0 to 5 C and adjusted by adding a 50 "nigen Sodium acetate solution has a pH of 4. A solution of the sodium salt is added to the slide solution of 24.3 parts of 2-amino-K-hydroxynaphtholv.iline-6-sulfonic acid in 250 parts of water slowly to. To
ίο Beendigung der Kupplung gibt man unter Rühren 300 Raumteile gesättigte Kochsalzlösung hin/j. saugt den ausgefallenen Farbstoff ab. wäscht ihn mit 10" niger Kochsalzlösung und trocknet ihn. Man erhält ein dunkelrotes Pulver, das sich in Wasser mit roter Farbeίο The coupling is terminated while stirring 300 parts by volume of saturated saline solution to / j. sucks the precipitated dye from. washes it with 10 "niger Saline and dries it. A dark red powder is obtained which turns red in water in water
τ5 löst und auf Polyamidgewebe blaustichigrote Färbungen von vorzüglichen Echtheiten erzeugt.τ5 dissolves and blue-tinged red dyeings on polyamide fabric of excellent fastness properties.
Auf entsprechende Weise erhält man mit derselben Kupplungskomponente unter Verwendung der in der Tabelle angegebenen Diazokomponenten Farbstoffe, die Färbungen mit dem angegebenen Farbton ergeben.In a corresponding manner, one obtains with the same coupling component using the in the Table indicated diazo components dyes which result in colorations with the indicated hue.
in der R die oben angegebene Bedeutung hat. in saurem Mei'ium mit l-Amino-S-hydroxynaphthalin-o-sulfonsäure kuppelt.in which R has the meaning given above. in sour Mei'ium with l-amino-S-hydroxynaphthalene-o-sulfonic acid clutch.
Als Diazokomponenten kommen die Derivate des 3- oder 4-Aminophthalsäureimids in Betracht.The derivatives of 3- or 4-aminophthalimide are suitable as diazo components.
Die Verbindungen der Formel II können in üblicher Weise diazotiert werden, nämlich in Gegenwart verdünnter Salz- oder Schwefelsäure in Wasser oder im Gemisch von Wasser mit organischen Lösungsmitteln. Beim Kuppeln wählt man zweckmäßig den pH-Bereich so stark mineralsauer, daß die Reaktion gerade noch abläuft.The compounds of the formula II can be used in a customary manner Way to be diazotized, namely in the presence of dilute hydrochloric or sulfuric acid in water or im Mixture of water with organic solvents. When coupling, it is advisable to choose the pH range so strongly minerally acidic that the reaction just takes place.
Die neuen Farbstoffe ergeben auf Wolle. Seide oder synthetischen Polyamidfasern aus saurem Bad blaustichigrote bis bordofarbcnc Färbungen von sehr guten Lichtechtheiten. Die neuen Farbstoffe haben ein genügendes bis sehr gutes Egalisiervermögen und ergeben Färbungen mit guten bis sehr guten Naßcchtheitcn. The new dyes result on wool. Silk or synthetic polyamide fibers from acid bath blue-tinged red to bordo color dyeings with very good lightfastnesses. The new dyes have a Sufficient to very good leveling power and result in dyeings with good to very good wet fastness properties.
Gegenüber einem aus der französischen Patentschrift 828 769 bekannten nächslvergleichbaren Farbstoff haben die ernndungsgcmäßcn Farbstoffe Vorteile in der Naßechtheit.Compared to a next-comparable dye known from French patent specification 828 769 the dyes according to the specification have advantages in terms of wet fastness.
Sofern nicht anders vermerkt, bezichen sich Angaben über Teile und Prozente in den folgenden Beispielen aufUnless otherwise noted, the information is referenced about parts and percentages in the following examples
das Gewicht. ,the weight. ,
Zu der Lösung von 23.S Teilen 3-Aminophthiilsaurephenylimid in 3(X) Raumteilen Eisessig und ?S Riiumteilen konzentrierter Salzsäure läßt man unterTo the solution of 23rd parts of 3-aminophthiilsaurephenylimide in 3 (X) parts by volume of glacial acetic acid and 5 parts of concentrated hydrochloric acid are added
2 32 3
Dia/iikomponenleSlide / iikomponenle
4-Aminophthalsäure-4-aminophthalic acid
phenylimid
3-Aminophthalsäurc-phenylimide
3-aminophthalic acid
2'-methoxyphenyl-2'-methoxyphenyl-
imidimid
4-Aminophthalsäure-2'-methoxyphcnylimid 4-aminophthalic acid-2'-methoxyphynylimide
Farbion tier Färbung
auf Polvamid oder WolleColoring animal coloring
on polvamid or wool
Blaustichigbordo
BlaustichigrotBluish bordeaux
Bluish red
BlaustichigbordoBluish bordeaux
Claims (2)
Family
ID=
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