CH265404A - Process for the preparation of a new monoazo dye. - Google Patents
Process for the preparation of a new monoazo dye.Info
- Publication number
- CH265404A CH265404A CH265404DA CH265404A CH 265404 A CH265404 A CH 265404A CH 265404D A CH265404D A CH 265404DA CH 265404 A CH265404 A CH 265404A
- Authority
- CH
- Switzerland
- Prior art keywords
- new
- preparation
- sulfuric acid
- red
- monoazo dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 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 title description 3
- 238000002360 preparation method Methods 0.000 title description 3
- 239000000975 dye Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 229920002301 cellulose acetate Polymers 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 230000001180 sulfating effect Effects 0.000 claims description 2
- 229920002955 Art silk Polymers 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid 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
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines neuen Monoazofarbstoffes. Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung eines neuen Azo- farbstoffes, gemäss welehem N-ss-Oxyäthvl- N-,6'-phenoxyäthylanilin, diazotiertes o-Chlor- p-nitranilin und ein Sulfatierungsmittel mit einander dermassen zur Umsetzung gebraeht werden, dass die Oxyäth.-,
Igruppe in die ent- spreehende Seh"vefelsäureestergriLppe über geführt wird und der Diazorest in bezug auf das tertiäre Stiekstoffatoni in 4-Stellung ein tritt.
Der neue Farbstoff bildet ein dunkelrotes Pulver, welches in W-asser unter Bildung einer roten Lösung und in konzentrierter Schwefelsäure unter Bildung einer rötlich- braunen Lösung löslieh ist und Cellulose- acetatkunstseide in karmesinroteil Farbtönen färbt.
<I>Beispiel:</I> Eine feine Suspension von<B>17,3</B> Teilen o-Chlor-p-nitranilin in<B>300</B> Teilen Wasser und <B>30</B> Teilen 36%ioer Salzsäure wird durch Zu gabe von<B>6,9</B> Teilen Natriumnitrit, gelöst in <B>50</B> Teilen Wasser, diazotiert. Die auf 511 <B>C</B> ge kühlte filtrierte Lösun- der Diazoverbindun-- wird langsam einer ähnlieh gekühlten Lösung von<B>35,
9</B> Teilen des Natriumsalzes des Seh-we- felsäureesters des N-ss-Oxyäth#,1-N-ss-phenoxy- äthylanilins in<B>400</B> Teilen Wasser unter Rühren zugesetzt. Nachdem das Gemiseh während<B>1</B> Stunde gerührt wurde, wird all- mählieh wässriges, 50%iges Natriumaeetat hinzugefügt, um das mineralsaure Kupp lungsmedium abzustumpfen.
Nach beendeter Kupplung wird die Suspension des Monoazo- farbstoffes durch Zugabe von 5n-Natrium- livdro.xydlösung auf Brillantgelb gerade alkalisch gestellt. Der Farbstoff wird abfil- triert, mit 21/'>%igem wässrigem. Natrium- ehlorid gewasehen und bei 30-40"C ge trocknet.
Der Sehweielsäureester des Ni-fl-Oxyäthyl- N-f)'-Phenoxyäthylanilins wird dureh Behan deln von N-ss-Oxyäthyl-N-ss'-pheno.xyäthyl- anilin mittels Chlorsulfonsäure in Tetrachlor- äthan erhalten.
Process for the preparation of a new monoazo dye. The present invention relates to a process for the preparation of a new azo dye, according to which N-ss-Oxyäthvl- N-, 6'-phenoxyethylaniline, diazotized o-chloro-p-nitroaniline and a sulfating agent are used to react with one another in such a way that the oxyether,
I group is carried over into the corresponding Seh “vefelsäureestergriLppe and the diazo radical occurs in relation to the tertiary Stiekstoffatoni in 4-position.
The new dye forms a dark red powder which is soluble in water to form a red solution and in concentrated sulfuric acid to form a reddish-brown solution and dyes cellulose acetate silk in shades of crimson red.
<I> Example: </I> A fine suspension of <B> 17.3 </B> parts of o-chloro-p-nitroaniline in <B> 300 </B> parts of water and <B> 30 </ B > Parts of 36% hydrochloric acid are diazotized by adding <B> 6.9 </B> parts of sodium nitrite dissolved in <B> 50 </B> parts of water. The filtered solution of diazo compound cooled to 511 <B> C </B> slowly becomes a similarly cooled solution of <B> 35,
9 parts of the sodium salt of the sodium sulfate of N-ß-Oxyäth #, 1-N-ß-phenoxyethylaniline in 400 parts of water are added with stirring. After the mixture has been stirred for 1 hour, aqueous 50% sodium acetate is gradually added in order to blunt the mineral acid coupling medium.
After the coupling has ended, the suspension of the monoazo dye is just made alkaline to brilliant yellow by adding 5N sodium hydroxide solution. The dye is filtered off with 21% strength aqueous. Sodium chloride was washed and dried at 30-40 ° C.
The Sehweiel acid ester of Ni-fl-Oxyäthyl- N-f) '- Phenoxyäthylanilins is obtained by treating N-ss-Oxyäthyl-N-ss'-pheno.xyäthylaniline by means of chlorosulfonic acid in tetrachloroethane.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB265404X | 1944-08-28 | ||
| CH251389T | 1945-08-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH265404A true CH265404A (en) | 1949-11-30 |
Family
ID=25729530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH265404D CH265404A (en) | 1944-08-28 | 1945-08-28 | Process for the preparation of a new monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH265404A (en) |
-
1945
- 1945-08-28 CH CH265404D patent/CH265404A/en unknown
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