AT272473B - Process for the production of a new, substantive, yellow dye - Google Patents
Process for the production of a new, substantive, yellow dyeInfo
- Publication number
- AT272473B AT272473B AT632767A AT632767A AT272473B AT 272473 B AT272473 B AT 272473B AT 632767 A AT632767 A AT 632767A AT 632767 A AT632767 A AT 632767A AT 272473 B AT272473 B AT 272473B
- Authority
- AT
- Austria
- Prior art keywords
- parts
- substantive
- new
- dye
- yellow dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 title claims description 3
- 239000001043 yellow dye Substances 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 4
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 claims description 3
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 3
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 claims description 3
- 239000007859 condensation product Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 239000000203 mixture Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 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
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Landscapes
- Coloring (AREA)
- Paper (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Herstellung eines neuen, substantiven, gelben Farbstoffes
EMI1.1
EMI1.2
Es wurde nun gefunden, dass man einen grüneren brillanteren Farbstoff mit wesentlich besserem neutralem Ziehvermögen und günstigerem Temperaturverhalten bei der Kombination mit Wollfarbstoffen erhält, wenn man 2 Mol diazotierte 2-Aminonaphthalin-4,8-disulfosäure essigsauer auf 2 Mol 1-Amino- - 2-methoxy-5-methylbenzol kuppelt, den entstandenen Monoazofarbstoff nach der Isolierung mit 1 Mol Cyanurchlorid stufenweise kondensiert und das Kondensationsprodukt mehrere Stunden bei erhöhter Temperatur in alkalischem Milieu hydrolysiert. Anschliessend wird in üblicher Weise aufgearbeitet.
Der erhaltene Farbstoff besitzt folgende Konstitutionsformel
EMI1.3
Beispiel: 30,3 Teile 2-Aminonaphthalin-4, 8-disulfosäure werden in 200 Teilen Wasser und 24 Teilen Salzsäure angeschlämmt und bei 100 C mit 7 Teilen Natriumnitrit diazotiert. 13, ? Teile
<Desc/Clms Page number 2>
l-Amino-2-methoxy-5-methylbenzol werden in 100 Teilen Wasser und 20 Teilen Salzsäure bei etwas erhöhter Temperatur gelöst. Diese Lösung lässt man zur diazotierten Komponente zulaufen, und anschliessend werden noch 16 Teile Natriumacetat in wässeriger Lösung zugetropft. Die Kupplung ist nach sechssttindigem Rühren beendet.
Durch Zugabe von 60 Teilen Natriumchlorid wird der entstandene Monoazofarbstoff ausgesalzen und abgesaugt. Anschliessend wird der Nutschkuchen in 500 Teilen Wasser unter Zusatz von 4 Teilen Soda gelöst. 9,2 Teile Cyanurchlorid werden in 50 Teilen Wasser unter Zusatz von 0, 1 Teilen eines im wesentlichen Ammonsalze von Ligninsulfonsäuren enthaltenden Präparats angeschlämmt. Jetzt wird bei 00 C die Lösung des Monoazofarbstoffes zugegeben und 2 h bei PH 7 kondensiert. Anschliessend wird auf 400 C angewärmt und 3 h bei dieser Temperatur und PH 7 kondensiert. Der pH-Wert wird durch Zugabe von Soda bei 7 gehalten. Zur Hydrolyse wird dann auf 900 C erwärmt und unter Zusatz von 4 Teilen Soda diese Temperatur 2 h gehalten. Durch Zugabe von 150 Teilen Natriumchlorid wird der Farbstoff dann ausgesalzen, abgesaugt und bei 900 C getrocknet.
Der Farbstoff bildet ein gelbbraunes kristallines Pulver, das Cellulosefasern in brillantem grünstichig gelbem Ton färbt.
<Desc / Clms Page number 1>
Process for the production of a new, substantive, yellow dye
EMI1.1
EMI1.2
It has now been found that a greener, more brilliant dye with significantly better neutral drawability and more favorable temperature behavior when combined with wool dyes is obtained if 2 moles of diazotized 2-aminonaphthalene-4,8-disulfonic acid are acetic acid to 2 moles of 1-amino- 2 -methoxy-5-methylbenzene, the resulting monoazo dye is gradually condensed after isolation with 1 mol of cyanuric chloride and the condensation product is hydrolyzed for several hours at an elevated temperature in an alkaline medium. It is then worked up in the usual way.
The dye obtained has the following constitutional formula
EMI1.3
Example: 30.3 parts of 2-aminonaphthalene-4, 8-disulfonic acid are suspended in 200 parts of water and 24 parts of hydrochloric acid and diazotized at 100 ° C. with 7 parts of sodium nitrite. 13,? Parts
<Desc / Clms Page number 2>
1-Amino-2-methoxy-5-methylbenzene is dissolved in 100 parts of water and 20 parts of hydrochloric acid at a slightly elevated temperature. This solution is allowed to run into the diazotized component, and then 16 parts of sodium acetate in aqueous solution are added dropwise. The coupling is complete after stirring for six hours.
The monoazo dye formed is salted out by adding 60 parts of sodium chloride and filtered off with suction. The filter cake is then dissolved in 500 parts of water with the addition of 4 parts of soda. 9.2 parts of cyanuric chloride are suspended in 50 parts of water with the addition of 0.1 part of a preparation containing essentially ammonium salts of lignosulfonic acids. The solution of the monoazo dye is now added at 00 ° C. and the mixture is condensed at pH 7 for 2 h. It is then warmed to 400 C and condensed at this temperature and pH 7 for 3 h. The pH is kept at 7 by adding soda. For hydrolysis, the mixture is then heated to 900 ° C. and maintained at this temperature for 2 hours with the addition of 4 parts of soda. The dye is then salted out by adding 150 parts of sodium chloride, filtered off with suction and dried at 900.degree.
The dye forms a yellow-brown crystalline powder that dyes cellulose fibers in a brilliant greenish yellow shade.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD12347767 | 1967-03-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT272473B true AT272473B (en) | 1969-07-10 |
Family
ID=5479265
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT632767A AT272473B (en) | 1967-03-20 | 1967-07-06 | Process for the production of a new, substantive, yellow dye |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT272473B (en) |
-
1967
- 1967-07-06 AT AT632767A patent/AT272473B/en active
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