CH306269A - Process for the preparation of a substantive azo dye. - Google Patents
Process for the preparation of a substantive azo dye.Info
- Publication number
- CH306269A CH306269A CH306269DA CH306269A CH 306269 A CH306269 A CH 306269A CH 306269D A CH306269D A CH 306269DA CH 306269 A CH306269 A CH 306269A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- copper
- parts
- preparation
- gray
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 239000000987 azo dye Substances 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 230000008878 coupling Effects 0.000 claims description 5
- 238000010168 coupling process Methods 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- -1 amino monoazo Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 150000008049 diazo compounds Chemical class 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- QKSIFUGZHOUETI-UHFFFAOYSA-N copper;azane Chemical compound N.N.N.N.[Cu+2] QKSIFUGZHOUETI-UHFFFAOYSA-N 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 150000004699 copper complex Chemical class 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 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 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/08—Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 303281. Verfahren zur Herstellung eines direktziehenden Azofarbstoffes. Es wurde gefunden, dass man zu einem wertvollen direktziehenden Azofarbstoff ge- langt, wenn.
man eine Diazoverbindung des Aminomonoazofarbstoffes der Formel
EMI0001.0006
niit 2-Berizoylamino-5-oxynaphtha.lin-7-sulfon- säitre kuppelt und den so erhaltenen Disazo- farbstoff in der Weise mit kupferabgebenden Mitteln behandelt, dass unter Aufspaltung der -0--Mlzyl-Gruppe der o,o'-Dioxyazo-Kupfer- komplex entsteht.
Der neue Farbstoff bildet ein dunkles Pul ver, das sieh in Wasser mit graublauer Farbe löst und Baumwolle in graublauen Tönen von sehr guten färbt.
Der Aminomonoazofarbstoff der obigen Formel wird zweckmässig dureh Kupplung von dianotierter 4-Amino-4'-ehlorstilben-2,2'- !lisulfonsäitre mit 1-Amino-2-methoxv-5-me- t.liylbenzol in saurem bis neutralem Me erhalten. Die Kupplung der Diazo- azoverbindung mit der 2-Benzoylamino-5-oxy- tiapht.balin-7-sulforlsäure erfolgt mit Vorteil in alka.lisehem Medium, und es empfiehlt sieh, ein die Kupplung förderndes Mittel, z. B.
Pyridin, zuzusetzen.
Als kupferabgebende Mittel kommen vor zugsweise Kupfertetramminkomplexe in Be- traelit, und die Kupferung erfolgt zweckmässig während mehrerer Stunden in der Nähe von i001' in wässerigem Medium. Es ist auch vor- teilhaft, in Gegenwart von Oxyalkylaminen, insbesondere Äthanolamin bzw. den sich von diesen Aminen ableitenden Kupferkomplexen zu arbeiten.
<I>Beispiel:</I> 38,9 Teile 4-Amino-4'-chlorstilbell-2,2'-di- sulfonsäure werden in 150 Teilen Wasser gelöst, mit 25 Teilen 30o/oiger Salzsäure ver setzt und mit 6,9 Teilen Natriumnitrit in 50 Teilen Wasser diazotiert. Zu der Diazover- bindung wird eine salzsaure Lösung von 13,7 Teilen 1-Amino-2-methoxy-5-methylbenzol hin zugefügt.
Durch Zugabe von Natriumacetat bis zur kongoneutralen Reaktion und Rühren über Nacht wird der Monoazofarbstoff gebil det. Der abgeschiedene Farbstoff wird abfil- t.riert.
Der feuchte Farbstoffkixchen wird unter Zusatz von Natriümhydroxyd in 1000 Teilen Wasser gelöst, 6,9 Teile Natriumnitrit in 50 Teilen Wasser werden zugesetzt und bei :i bis 10 unter gutem Rühren 40 Teile 30%ige Salzsäure eingestürzt. In 2 bis 3 Stunden ist die Dianotierung beendet.
Hierauf wird die Diazoverbindung in eine Lösung aus 35 Tei len 2-Benzoylamino-5-oxynaphthalin-7-sulfon- säure, 200 Teilen Wasser und 40 Teilen Na- triumcarbonat eingetragen und 10 bis 12 Stun den gerührt. Nach beendeter Kupplung wird der Disazofarbstoff ausgesalzen, filtriert und zwecks Überführung in den Kupferkomplex 5 Stunden mit 25 Teilen krist. Kupfersulfat, 50 Teilen 25 % igem Ammoniak und 20 Teilen Äthanolamin in 2000 Teilen Wasser am Rück- fluss gekocht.
Der mit Natriumehlorid abge schiedene Farbstoff wird filtriert und ge trocknet.
<B> Additional patent </B> to main patent no. 303281. Process for the production of a substantive azo dye. It has been found that a valuable substantive azo dye can be obtained if.
one is a diazo compound of the amino monoazo dye of the formula
EMI0001.0006
niit 2-berizoylamino-5-oxynaphtha.lin-7-sulfonic acid coupled and treated the disazo dye thus obtained in such a way that with splitting of the -0 - Mlzyl group of the o, o'-dioxyazo -Copper complex arises.
The new dye forms a dark powder that dissolves in water with a gray-blue color and dyes cotton very good in gray-blue tones.
The amino monoazo dye of the above formula is conveniently obtained by coupling dianotated 4-amino-4'-chlorostilbene-2,2'-lisulphonic acid with 1-amino-2-methoxy-5-methylbenzene in acidic to neutral Me. The coupling of the diazo azo compound with the 2-benzoylamino-5-oxy- tiapht.balin-7-sulforic acid is advantageously carried out in alkali medium, and it is recommended to use an agent promoting the coupling, e.g. B.
Pyridine, add.
Copper tetrammine complexes are preferably used as copper-releasing agents in Betraelite, and coppering is expediently carried out for several hours in the vicinity of 1001 'in an aqueous medium. It is also advantageous to work in the presence of oxyalkylamines, in particular ethanolamine or the copper complexes derived from these amines.
<I> Example: </I> 38.9 parts of 4-amino-4'-chlorostilbone-2,2'-disulfonic acid are dissolved in 150 parts of water, mixed with 25 parts of 30% hydrochloric acid and mixed with 6, 9 parts of sodium nitrite in 50 parts of water are diazotized. A hydrochloric acid solution of 13.7 parts of 1-amino-2-methoxy-5-methylbenzene is added to the diazo compound.
The monoazo dye is formed by adding sodium acetate until a Congo-neutral reaction and stirring overnight. The deposited dye is filtered off.
The moist little dye is dissolved in 1000 parts of water with the addition of sodium hydroxide, 6.9 parts of sodium nitrite in 50 parts of water are added and 40 parts of 30% hydrochloric acid are collapsed at: 1 to 10 with thorough stirring. The dianotation is finished in 2 to 3 hours.
The diazo compound is then added to a solution of 35 parts of 2-benzoylamino-5-oxynaphthalene-7-sulphonic acid, 200 parts of water and 40 parts of sodium carbonate and the mixture is stirred for 10 to 12 hours. After coupling is complete, the disazo dye is salted out, filtered and, for the purpose of conversion into the copper complex, crystallized with 25 parts for 5 hours. Copper sulfate, 50 parts of 25% ammonia and 20 parts of ethanolamine in 2000 parts of water are refluxed.
The dyestuff deposited with sodium chloride is filtered and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH303281T | 1951-11-12 | ||
| CH306269T | 1951-11-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH306269A true CH306269A (en) | 1955-03-31 |
Family
ID=25734619
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH306269D CH306269A (en) | 1951-11-12 | 1951-11-12 | Process for the preparation of a substantive azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH306269A (en) |
-
1951
- 1951-11-12 CH CH306269D patent/CH306269A/en unknown
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