CH287108A - Process for the preparation of a chromium-containing azo dye. - Google Patents
Process for the preparation of a chromium-containing azo dye.Info
- Publication number
- CH287108A CH287108A CH287108DA CH287108A CH 287108 A CH287108 A CH 287108A CH 287108D A CH287108D A CH 287108DA CH 287108 A CH287108 A CH 287108A
- Authority
- CH
- Switzerland
- Prior art keywords
- chromium
- ehrom
- azo dye
- gray
- dyes
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 239000000987 azo dye Substances 0.000 title claims description 7
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims description 5
- 229910052804 chromium Inorganic materials 0.000 title claims description 5
- 239000011651 chromium Substances 0.000 title claims 3
- 239000000975 dye Substances 0.000 claims description 11
- 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 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001845 chromium compounds Chemical class 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000001684 chronic effect Effects 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
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/16—Monoazo compounds containing chromium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. <B>284075.</B> Verfahren zur Herstellung eines ehromhaltigen Azofarbstoffes. Es wurde gefunden, dass inan zu einem neuen wertvollen, ehromhaltigen Azofarbstoff gelangt, wenn man auf ein Gemisch der zwei Monoazolarbstoffe, die den folgenden For meln
EMI0001.0009
entsprechen, ehromabgebende Mittel derart einwirken lässt,
dass ein ehromhaltiger Azo- farbstoff entsteht, der<B>je</B> ein Molekül der zwei Ausgangsmonoazofarbstoffe an ein Chrom atom komplex gebunden enthält.
Der neue ellromhaltigle Farbstoff bildet ein graues Pulver, das sich in Wasser mit rotstiehig grauer und in konzentrierter Sehwe- felsäure mit violetter Parbe löst Lind Wolle aus neutralem oder schwach essigsaurem Bade in rotstiehig grauen Tönen färbt.
Die zwei beim vorliegenden Verfahren als Ausgangsstoffe dienenden Monoazofarbstoffe können nach an sieh bekannten Methoden her gestellt werden, indem man diazotiertes 5- Nitro-2-amino-l-oxybenzol mit 1-Aeetylamino- 7-oxynaphthalin und diazotiertes 2-Amino-1 - ox.ybenzol-4-sullonsäureamid mit 2-Oxynapli,
- thalin jeweils in alkaliseliem Medi-Liiii. kuppelt.
Über die zu verwendenden ehromabgeben- den Mittel und Reaktionsbedingungen gibt das Hauptpatent Auskunft. <I>Beispiel:</I> <B>18,8</B> Teile 2<B>-</B> Amino <B>- 1 -</B> oxybenzol <B>-</B> 4-sulf on- sä-Lireaniid werden in 200 Teilen Wasser und <B>15</B> Volumteilen 10-n-Salzsälire aufgesehlämmt und bei<B>5</B> bis 1011 mit<B>25</B> Volumteilen 4-n-Na-
triumnitritlösung diazotiert. Die durch Zu gabe von Natriumearbonat neutralisierte Di- azoverbindung lässt man einlaufen in eine mit <B>E</B> Gis auf<B>0'</B> abgekühlte Lösung von 14,8 Teilen 2-Oxynaphthalin in<B>52</B> Volumteilen 2-n-Na- triumhydroxydlösung und<B>50</B> Volumteilen 2-n- Natriumearbonatlösung. Naeb,
beendeter Kupp lung wird der abgesehiedene Farbstoff fil triert und mit verdünnter Natriumehlorid- lösung gewaschen und getrocknet.<B>36,6</B> Teile cles so erhaltenen Farbstoffes und<B>36,
6</B> Teile des aus 5-i\Titro-2-amino-l-oxybenzol und 1- zleetylamino-7-oxynaphthalin nach ähnlicher Methode erhaltenen Farbstoffes werden in <B>3000</B> Teilen Wasser aufgesehlämmt und mit 220 Teilen einer Lösung von ehronisalieyl- saurem Natrium mit einern Chronigehalt von 2,
6% versetzt. 'Nach <B>6</B> Stunden Kochen am Rückflusskühler ist die Chromierung beendet. Die erhaltene Chromverbindung wird durch ';atri-Limehloridzugabe abgeschieden und ab- filtriert.
Additional patent to main patent no. <B> 284075. </B> Process for the production of an azo dye containing Ehrom. It has been found that a new valuable, Ehrom-containing azo dye is obtained when a mixture of the two monoazolar materials having the following formulas is used
EMI0001.0009
correspond to, allows honor donors to act in such a way,
that an azo dye containing Ehrom is formed, which contains <B> each </B> one molecule of the two starting monoazo dyes bound to a chromium atom in a complex.
The new ellromic dye forms a gray powder, which dissolves in water with reddish gray and in concentrated sulphurous acid with violet color, and wool from neutral or weakly acetic acid dyes in reddish gray tones.
The two monoazo dyes used as starting materials in the present process can be made by methods known per se by diazotized 5-nitro-2-amino-1-oxybenzene with 1-ethylamino-7-oxynaphthalene and diazotized 2-amino-1-ox .ybenzene-4-sulphonic acid amide with 2-oxynapli,
- thalin in alkaliseliem Medi-Liiii. clutch.
The main patent provides information about the atom-releasing agents and reaction conditions to be used. <I> Example: </I> <B> 18.8 </B> Part 2 <B> - </B> Amino <B> - 1 - </B> oxybenzene <B> - </B> 4 -sulf on-sä-lireaniid are slurried in 200 parts of water and <B> 15 </B> parts by volume of 10-n salt saline and <B> 5 </B> to 1011 with <B> 25 </B> parts by volume 4-n-Na-
trium nitrite solution diazotized. The diazo compound neutralized by adding sodium carbonate is allowed to run into a solution of 14.8 parts of 2-oxynaphthalene in 52, which has been cooled to <B> E </B> Gis to <B> 0 '</B> </B> parts by volume of 2-n sodium hydroxide solution and <B> 50 </B> parts by volume of 2-n sodium carbonate solution. Well,
When the coupling is completed, the separated dye is filtered off, washed with dilute sodium chloride solution and dried. <B> 36.6 </B> parts of the dye thus obtained and <B> 36,
6 parts of the dye obtained from 5-i \ titro-2-amino-1-oxybenzene and 1-zleetylamino-7-oxynaphthalene by a similar method are slurried in <B> 3000 </B> parts of water and mixed with 220 Dividing a solution of Ehronisalieyl acid sodium with a chronic content of 2,
6% offset. After <B> 6 </B> hours of boiling on the reflux condenser, the chromation is complete. The chromium compound obtained is separated off by adding atri-limestone chloride and filtered off.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH287108T | 1949-11-18 | ||
| CH284075T | 1949-11-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH287108A true CH287108A (en) | 1952-11-15 |
Family
ID=25732357
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH287108D CH287108A (en) | 1949-11-18 | 1949-11-18 | Process for the preparation of a chromium-containing azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH287108A (en) |
-
1949
- 1949-11-18 CH CH287108D patent/CH287108A/en unknown
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