CH181714A - Process for the preparation of a substantive copper-containing azo dye. - Google Patents
Process for the preparation of a substantive copper-containing azo dye.Info
- Publication number
- CH181714A CH181714A CH181714DA CH181714A CH 181714 A CH181714 A CH 181714A CH 181714D A CH181714D A CH 181714DA CH 181714 A CH181714 A CH 181714A
- Authority
- CH
- Switzerland
- Prior art keywords
- copper
- dye
- substantive
- containing azo
- azo dye
- Prior art date
Links
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims description 9
- 229910052802 copper Inorganic materials 0.000 title claims description 9
- 239000010949 copper Substances 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 6
- 239000000987 azo dye Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- 239000002253 acid Substances 0.000 claims description 3
- 239000012670 alkaline solution Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- -1 methoxyl group Chemical group 0.000 claims description 2
- 239000010446 mirabilite Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940000488 arsenic acid Drugs 0.000 description 1
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000003518 caustics Substances 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
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
Landscapes
- Coloring (AREA)
Description
verfahren zur Herstellung eines substantiven kupferhaltigen Azofarbstoffes. In dem Hauptpatent Nr.<B>170768</B> ist ein Verfahren zur Darstellung von kupferhal tigen Azofarbstoffen beschrieben worden, welches darin besteht, dass man Trisazofarb- stoffe der allgemeinen Formel
EMI0001.0007
worin R1 beliebig substituiert sein kann und R., den Rest einer Komponente der Naph- thalinreihe, welche mindestens eine Sulfon- säuregruppe enthält,
bedeutet, unter solchen Bedingungen mit kupferabgebenden Mitteln behandelt, ,dass die in R, in o-Stellung zur Azobrücke befindliche Methoxylgruppe ge- spalten wird.
Es wurde nun gefunden, dass man zu ähn lichen Ergebnissen kommt, wenn man als Ausgangsfarbstoffe des Verfahrens die Pro- dukte benutzt, welche durch Reduktion der Monoazofarbstoffe von der folgenden all gemeinen Formel
EMI0001.0026
worin R1 beliebig substituiert sein kann und R2 den Rest einer Komponente der Naph thalin- oder Carbazolreihe bedeutet, mit Trau benzucker oder seinen Äquivalenten (wie zum Beispiel arsenige Säure, Formaldehyd)
in ätzalkalischer Lösung entstehen und die wahrscheinlich die Konstitution von Disazo- azoxyfa.rbstoffen besitzen. Die Farbstoffe färben Baumwolle in durchweg etwas röteren Tönen als die Farbstoffe des Patentes Nr. 170768.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines .sub- stantiven, kupferhaltigen Azofarbstoffes. Es ist dadurch gekennzeichnet, dass man den durch Reduktion des Monoazofarbstoffes aus diazotiertem 5-Nitro-2-amino-l-methoxyben- zol und 1-Oxynalihthalin-3,6-disulfonsäure mit Traubenzucker in alkalischer Lösung er hältlichen Farbstoff mit einem kupferab gebenden Mittel unter solchen Bedingungen behandelt,
dass eine Aufspaltung der Me- thogylgruppe erfolgt.
<I>Beispiel:</I> 52,7 Gewichtsteile des Monoazofarbstof- fes aus dianotiertem 5-Nitro-2-amino-l-me- thoxybenzoil und dem Natriumsalz der 1 Oxy-naphthalin-3,6-disulfonsäure werden in 3000 Gewichtsteilen Wasser und 90 Ge wichtsteilen Natronlauge von 38 Be gelöst. Bei 75 bis<B>80'</B> wird unter Rühren langsam eine Lösung von 12 Gewichtsteilen Trauben zucker in 100 Gewichtsteilen Wasser zuge geben.
Wenn die Reduktion beendet ist, wird der Farbstoff durch Aussalzen und Trocknen isoliert. 100 Gewichtsteile des so erhaltenen Farbstoffes werden in 3500 Gewichtsteilen Wasser gelöst, und nach Zugabe einer Lö sung von 30 Gewichtsteilen kristallisiertem Kupfersulfat und 90 Gewichtsteilen 25 %igen Ammoniaks in 200 G ewiehtsteilen Wasser wird die Mischung 8 Stunden unter Rühren auf 80 bis 90 erhitzt. Der entstandene kupferhaltige Farbstoff wird durch Bus salzen und Trocknen isoliert.
Er stellt ein dunkles Pulver dar, das sich in Wasser mit brünstichig blauer Farbe löst. flus dem Glaubersalz-Sodabad wird die vegetabilische Faser in blauen Tönen von sehr guter Licht echtheit angefärbt.
process for the production of a substantive copper-containing azo dye. In the main patent no. <B> 170768 </B>, a method for the preparation of copper-containing azo dyes has been described, which consists in using trisazo dyes of the general formula
EMI0001.0007
where R1 can be substituted as desired and R., the remainder of a component of the naphthalene series, which contains at least one sulfonic acid group,
means, treated with copper-releasing agents under such conditions, that the methoxyl group in R 1 in o-position to the azo bridge is cleaved.
It has now been found that similar results are obtained if the starting dyes used for the process are the products which, by reducing the monoazo dyes, have the following general formula
EMI0001.0026
where R1 can be substituted as desired and R2 denotes the remainder of a component of the naphthalene or carbazole series, with gray sugar or its equivalents (such as arsenic acid, formaldehyde)
arise in caustic alkaline solution and which probably have the constitution of disazoazoxyfa.rbstoffen. The dyes generally dye cotton in slightly redder tones than the dyes of patent no. 170768.
The present patent relates to a process for the production of a .sub- stantiven, copper-containing azo dye. It is characterized in that the dye obtained by reducing the monoazo dye from diazotized 5-nitro-2-amino-1-methoxyben- zene and 1-oxynalithalene-3,6-disulfonic acid with grape sugar in alkaline solution is obtained with a copper-releasing agent treated under such conditions,
that a splitting of the methogyl group takes place.
<I> Example: </I> 52.7 parts by weight of the monoazo dye from dianotized 5-nitro-2-amino-1-methoxybenzoil and the sodium salt of 1-oxynaphthalene-3,6-disulfonic acid are used in 3000 parts by weight Water and 90 parts by weight of sodium hydroxide solution of 38 Be dissolved. At 75 to 80 ', a solution of 12 parts by weight of grape sugar in 100 parts by weight of water is slowly added with stirring.
When the reduction is complete, the dye is isolated by salting out and drying. 100 parts by weight of the dye thus obtained are dissolved in 3500 parts by weight of water, and after the addition of a solution of 30 parts by weight of crystallized copper sulfate and 90 parts by weight of 25% ammonia in 200 parts by weight of water, the mixture is heated to 80 to 90 hours with stirring. The resulting copper-containing dye is isolated by salting it and drying it.
It is a dark powder that dissolves in water with a heat-tinged blue color. During the Glauber's salt soda bath, the vegetable fibers are colored in blue tones with very good light fastness.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH170768T | 1933-08-19 | ||
| US181714XA | 1933-08-24 | 1933-08-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH181714A true CH181714A (en) | 1935-12-31 |
Family
ID=25718986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH181714D CH181714A (en) | 1933-08-19 | 1934-08-23 | Process for the preparation of a substantive copper-containing azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH181714A (en) |
-
1934
- 1934-08-23 CH CH181714D patent/CH181714A/en unknown
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