CH294247A - Process for the production of a brown, chromium-containing dye. - Google Patents
Process for the production of a brown, chromium-containing dye.Info
- Publication number
- CH294247A CH294247A CH294247DA CH294247A CH 294247 A CH294247 A CH 294247A CH 294247D A CH294247D A CH 294247DA CH 294247 A CH294247 A CH 294247A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- brown
- chromium
- production
- dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000011651 chromium Substances 0.000 title description 7
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title description 6
- 229910052804 chromium Inorganic materials 0.000 title description 6
- 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 9
- 239000000987 azo dye Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 210000002268 wool Anatomy 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000003795 chemical substances by application Substances 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
- 238000001914 filtration Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- AVQFHKYAVVQYQO-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonamide Chemical compound NC1=CC(S(N)(=O)=O)=CC=C1O AVQFHKYAVVQYQO-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
- JFIAZQYXEWGSCX-UHFFFAOYSA-N methyl N-(1-hydroxynaphthalen-2-yl)carbamate Chemical compound C(=O)(OC)NC1=C(C2=CC=CC=C2C=C1)O JFIAZQYXEWGSCX-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000725 suspension 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
- C09B45/01—Complex metal compounds of azo dyes characterised by the method of metallisation
-
- 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. 291812. Verfahren zur Herstellung eines braunen, ehromhaltigen Farbstoffes. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines braunen, ehromhaltigen Farbstoffes. Das Verfahren ist.
EMI0001.0007
mit chromabgebenden Mitteln in solchen Men gen behandelt, dass auf 2 Moleküle Azofarb- stoff mindestens 1 Atom entfällt.
Die erhaltene neue, gemischte Chromkom- plexverbindung stellt ein schwarzes Pulver dar, das Wolle aus schwach essigsaurem Bade in tiefbraunen Tönen färbt. Beispiel: 18,8 Teile 2-Amino-phenol-4-sulfamid wer den in 150 Teilen Wasser mit 17 Teilen kon zentrierter Salzsäure gelöst, auf 5 abgekühlt und durch Zugabe von 6,9 Teilen Natrium nitrit (als 33proz. Lösung) dianotiert. Durch Zugabe von Natriumhydrogenkarbonat wird die überschüssige Salzsäure neutralisiert.
Die neutrale Anschlämmung der Diazoniumver- bindung giesst man bei 3 in eine Lösung von 18,3 Teilen 1-Phenyl-3-methyl-5-pyrazolon in dadurch gekennzeichnet, dass man ein Gemisch äquimolekularerMengen der Azofarbstoffe
EMI0001.0022
200 Teilen Wasser und 20 Teilen wasserfreiem Natriumkarbonat.
Nachdem die Kupplung be endet ist, isoliert man den Farbstoff (Farb stoff I) durch Filtration. 18,7 Teile 2-Amino- phenol-4-methylsulfon werden in 150 Teilen Wasser mit 17 Teilen konzentrierter Salzsäure gelöst, auf 5 abgekühlt und unter zeitweiser Zugabe von Eis mit 6,9 Teilen Natriumnitrit 100 % (als 33proz. Lösung) versetzt.
Die Di- a,zoverbindung wird mit Natriumhydrogen- karbonat neutralisiert und bei 0 bis 3 in eine Lösung von 22,8 Teilen Carbomethoxyamino- naphthol-(1,7) in 250 Teilen Wasser, 10,5 Vo- lumteilen 10n-Natronlauge und 15 Teilen was serfreiem Natriumkarbonat gegossen. Die Kupplung ist nach einigen Stunden beendet.
Man erhitzt auf 70 , fällt. den teilweise in Lö sung gegangenen Farbstoff durch Zugabe von Natriumchlorid aus und filtriert ihn ab (Farbstoff II). Farbstoff I schlämmt man mit 37 Teilen Mononatriumsalz des Farbstoffes II in 2000 Teilen Wasser an, gibt 210 Teile einer Lösung von ehromsalieylsaurem Ammonium (ent sprechend 5,45 Teilen Cr) zu und erhitzt während 4 Stunden zum Sieden. Es bildet sieh eine schwarzbraune Lösung, die man mit Natriumchlorid versetzt. Dabei fällt der Mischkomplex aus. Er wird abfiltriert und getrocknet.
Er stellt ein schwarzes Pulver dar,
EMI0002.0008
mit ehromabgebenden Mitteln in solchen Men gen behandelt, dass auf 2 Moleküle Azofarb- stoff mindestens 1 Atom Chrom entfällt.
Die erhaltene neue gemischte Chrom komplexverbindung stellt ein schwarzes Pul- das Wolle aus schwach essigsaurem Bade in tiefbralanen Tönen von sehr guter Lichteeht- heit und guten Nassechtheiten färbt.
Additional patent to the main patent No. 291812. Process for the production of a brown, Ehrom-containing dye. The subject of the present patent is a process for the production of a brown, Ehrom-containing dye. The procedure is.
EMI0001.0007
Treated with chromium-releasing agents in such quantities that there are at least 1 atom per 2 molecules of azo dye.
The new, mixed chromium complex compound obtained is a black powder that dyes wool from a weakly acetic acid bath in deep brown shades. Example: 18.8 parts of 2-aminophenol-4-sulfamide are dissolved in 150 parts of water with 17 parts of concentrated hydrochloric acid, cooled to 5 and dianotized by adding 6.9 parts of sodium nitrite (as a 33% solution). The excess hydrochloric acid is neutralized by adding sodium hydrogen carbonate.
The neutral suspension of the diazonium compound is poured at 3 into a solution of 18.3 parts of 1-phenyl-3-methyl-5-pyrazolone, characterized in that a mixture of equimolecular amounts of the azo dyes is used
EMI0001.0022
200 parts of water and 20 parts of anhydrous sodium carbonate.
After the coupling has ended, the dye (dye I) is isolated by filtration. 18.7 parts of 2-aminophenol-4-methylsulfone are dissolved in 150 parts of water with 17 parts of concentrated hydrochloric acid, cooled to 5 and mixed with 6.9 parts of 100% sodium nitrite (as a 33% solution) with the occasional addition of ice.
The di-a, zo compound is neutralized with sodium hydrogen carbonate and at 0 to 3 in a solution of 22.8 parts of carbomethoxyaminonaphthol (1.7) in 250 parts of water, 10.5 parts by volume of 10N sodium hydroxide solution and 15 Share what was poured anhydrous sodium carbonate. The coupling is complete after a few hours.
It is heated to 70%. the dye, which has partially gone into solution, by adding sodium chloride and filtering it off (dye II). Dye I is slurried with 37 parts of the monosodium salt of dye II in 2000 parts of water, 210 parts of a solution of Ehromsalieylsaurem ammonium (accordingly 5.45 parts of Cr) are added and the mixture is heated to the boil for 4 hours. A black-brown solution forms to which sodium chloride is added. The mixed complex precipitates in the process. It is filtered off and dried.
It represents a black powder
EMI0002.0008
Treated with chromium-releasing agents in such quantities that there is at least 1 atom of chromium for every 2 molecules of azo dye.
The new mixed chromium complex compound obtained is a black powder that dyes wool from weakly acetic acid bath in deep bralan shades of very good lightfastness and good wet fastness properties.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH294247T | 1951-01-11 | ||
| CH291812T | 1951-01-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH294247A true CH294247A (en) | 1953-10-31 |
Family
ID=25733154
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH294247D CH294247A (en) | 1951-01-11 | 1951-01-11 | Process for the production of a brown, chromium-containing dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH294247A (en) |
-
1951
- 1951-01-11 CH CH294247D patent/CH294247A/en unknown
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