CH148117A - Process for the production of a new chromium-containing dye. - Google Patents
Process for the production of a new chromium-containing dye.Info
- Publication number
- CH148117A CH148117A CH148117DA CH148117A CH 148117 A CH148117 A CH 148117A CH 148117D A CH148117D A CH 148117DA CH 148117 A CH148117 A CH 148117A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- amino
- parts
- chromium
- oxynaphthalene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims 2
- 229910052804 chromium Inorganic materials 0.000 title claims 2
- 239000011651 chromium Substances 0.000 title claims 2
- 239000000975 dye Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 229920002955 Art silk Polymers 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000004627 regenerated cellulose Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 229910021653 sulphate ion Inorganic materials 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- 150000001845 chromium compounds Chemical class 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GRWVQDDAKZFPFI-UHFFFAOYSA-H chromium(III) sulfate Chemical compound [Cr+3].[Cr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRWVQDDAKZFPFI-UHFFFAOYSA-H 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- BFMYDTVEBKDAKJ-UHFFFAOYSA-L disodium;(2',7'-dibromo-3',6'-dioxido-3-oxospiro[2-benzofuran-1,9'-xanthene]-4'-yl)mercury;hydrate Chemical compound O.[Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC(Br)=C([O-])C([Hg])=C1OC1=C2C=C(Br)C([O-])=C1 BFMYDTVEBKDAKJ-UHFFFAOYSA-L 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 229910021563 chromium fluoride Inorganic materials 0.000 description 1
- QOWZHEWZFLTYQP-UHFFFAOYSA-K chromium(3+);triformate Chemical compound [Cr+3].[O-]C=O.[O-]C=O.[O-]C=O QOWZHEWZFLTYQP-UHFFFAOYSA-K 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000001704 evaporation Methods 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
- -1 naphthol ester Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 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
Verfahren zur Herstellung eines neuen ehromlialtigen Farbstoffes. <B>Es</B> wurde gefunden, dass man einen neuen ehromhaltigen Farbstoff erhält, wenn man<B>1</B> Mol diazotiertes 5-Nitro-2-amirio-l-phenol, <B>1</B> Mol 2-Amino-5-oxynaphthalin-7-sulfosäure, <B>1</B> Mol p-Toluolsulfochlorid und ein ehromab- gebendes Mittel derart aufeinander einwirken lässt,
dass die Chromverbindung des Farb stoffs der Formel
EMI0001.0017
entsteht. Der gebildete Farbstoff stellt ein dunkles Pulver dar, das sich in Wasser und ver dünnten Alkalien mit grüner und in konz. Schwefelsäure mit blauroter Farbe löst. Er färbt Kunstseide ans regenerierter Zellulose in egalen grünen Tönen von sehr guter Echtheit. <I>Beispiel<B>1:</B></I> 24 Teile 2-Amiiio-5-oxynaphthalin-7-stil- fosäure werden in Gegenwart von freiem Alkali mit 20 Teilen p-TolLiolsulfochlorid in den Naphtholester übergeführt.
Dieser wird in Gegenwart von freier Säure mit dem Dia- zokÖrper aus<B>16</B> Teilen 5-Niti-o-2-amino-l- phenol kombiniert und der Farbstoff nach beendeter Kupplung abgeschieden. Er wird in<B>3000</B> Teilen heissem Wasser gelöst; dann fügt man<B>11</B> Teile Cr20,i in Form von Chrom- fluorid, Chromformiat oder Chromsulfat zu und erwärmt während<B>15</B> Stunden zum Ko chen unter Ersatz des verdampfenden Wassers. Die neue Chromverbindung fällt aus der Lösung aus; sie wird filtriert und getrocknet.
<I>Beispiel 2:</I> 40 Teile des durch Kupplung in Gegen wart einer Säure erhaltenen Monoazofarb- stoffes aus<B>15,5</B> Teilen diazotiertern 5-Nitro- 2-amino-l-phenol und 24 Teilen 2-Amino-5- oxynaphthalin-7-sulfosäure werden in<B>300</B> Teilen Wasser gelöst, mit 20 Teilen Natron- lauge (40 %ig)
versetzt und auf 950 erwärmt. Dazu gibt man nun 20 Teile p-Toluolsulfo- chlorid und rührt bis zum Verschwinden desselben. Darauf verdünnt man mit 200 Teilen Wasser, stellt mit Flusssäure neutral und versetzt mit der Fluorchromlösung aus <B>15</B> Teilen Cr203. Unter Rühren erwärmt man rückfliessend<B>15</B> Stunden zum Sieden. Darauf fällt man die Chromverbindung mit Kochsalz aus, filtriert und trocknet.
<I>Beispiel<B>3:</B></I> 15,4 Teile 6-Nitro-2-aniino-l-phenol wer den diazotiert und in Gegenwart einer Säure mit<B>23,9</B> Teilen 2-Amiiio-5-oxynaphthalin-7- sulfosäure zum Azofarbstoff kombiniert. Dieser wird durch Kochen Mit FlUorchrom- oder Chromsulfatlösung aus<B>15</B> Teilen Cr20s in die grüne Cbromverbindung übergeführt, die isoliert wird.
Man löst sie in 200 Teilen Wasser und stellt mit 20 Teilen Natron- lauge (40%ig) alkalisch, erwärmt auf 950 und versetzt mit 20 Teilen p-Toltiolsulfo- chlorid. Man rührt solange, bis dieses ver schwunden ist, scheidet den Farbstoff mit Kochsalz ab, filtriert und trocknet.
Process for the preparation of a new genuine dye. It has been found that a new Ehrom-containing dye is obtained if <B> 1 </B> mol of diazotized 5-nitro-2-amirio-1-phenol, <B> 1 </ B > Moles of 2-amino-5-oxynaphthalene-7-sulfonic acid, <B> 1 </B> moles of p-toluenesulfochloride and an oromolytic agent act on one another in such a way that
that the chromium compound of the dye of the formula
EMI0001.0017
arises. The dye formed is a dark powder that dissolves in water and dilute alkalis with green and conc. Sulfuric acid dissolves with a blue-red color. It dyes artificial silk and regenerated cellulose in level green shades of very good fastness. <I> Example <B>1:</B> </I> 24 parts of 2-amino-5-oxynaphthalene-7-stilfoic acid are converted into the naphthol ester in the presence of free alkali with 20 parts of p-TolLiolsulfochlorid.
This is combined in the presence of free acid with the diazo body made up of 16 parts of 5-nitro-o-2-amino-1-phenol and the dye is deposited after coupling has ended. It is dissolved in <B> 3000 </B> parts of hot water; then <B> 11 </B> parts of Cr20, i are added in the form of chromium fluoride, chromium formate or chromium sulfate and heated for <B> 15 </B> hours to cook while replacing the evaporating water. The new chromium compound falls out of solution; it is filtered and dried.
<I> Example 2: </I> 40 parts of the monoazo dye obtained by coupling in the presence of an acid from <B> 15.5 </B> parts of diazotized 5-nitro-2-amino-1-phenol and 24 Parts of 2-amino-5-oxynaphthalene-7-sulfonic acid are dissolved in <B> 300 </B> parts of water, mixed with 20 parts of sodium hydroxide solution (40%)
added and heated to 950. 20 parts of p-toluenesulphochloride are then added and the mixture is stirred until it disappears. It is then diluted with 200 parts of water, neutralized with hydrofluoric acid and mixed with the fluorochrome solution of 15 parts Cr203. The mixture is refluxed for <B> 15 </B> hours and heated to boiling while stirring. The chromium compound is then precipitated with common salt, filtered and dried.
<I> Example <B>3: </B> </I> 15.4 parts of 6-nitro-2-aniino-1-phenol are diazotized and in the presence of an acid with <B> 23.9 </ B > Share 2-Amiiio-5-oxynaphthalene-7-sulfonic acid combined to form the azo dye. This is converted into the green chromium compound by boiling with fluorochrome or chromium sulfate solution from <B> 15 </B> parts of Cr20s, which is isolated.
They are dissolved in 200 parts of water and made alkaline with 20 parts of sodium hydroxide solution (40%), heated to 950 and mixed with 20 parts of p-tolentiol sulfochloride. The mixture is stirred until this has disappeared, the dye is separated off with sodium chloride, filtered and dried.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH148117T | 1930-01-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH148117A true CH148117A (en) | 1931-07-15 |
Family
ID=4404006
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH148117D CH148117A (en) | 1930-01-23 | 1930-01-23 | Process for the production of a new chromium-containing dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH148117A (en) |
-
1930
- 1930-01-23 CH CH148117D patent/CH148117A/en unknown
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