CH268075A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH268075A CH268075A CH268075DA CH268075A CH 268075 A CH268075 A CH 268075A CH 268075D A CH268075D A CH 268075DA CH 268075 A CH268075 A CH 268075A
- Authority
- CH
- Switzerland
- Prior art keywords
- azo dye
- parts
- preparation
- red
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 239000000987 azo dye Substances 0.000 title claims description 4
- 239000002253 acid Substances 0.000 claims description 5
- 239000000975 dye Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- RBSJXSHUNMWICQ-UHFFFAOYSA-N 2-methoxy-5-(2-methylbutan-2-yl)aniline Chemical compound CCC(C)(C)C1=CC=C(OC)C(N)=C1 RBSJXSHUNMWICQ-UHFFFAOYSA-N 0.000 description 2
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical group CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentaoxide Chemical compound [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000011780 sodium chloride 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/16—Naphthol-sulfonic acids
-
- 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
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
- C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
- C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Azofarbstoffes. Es wurde gefunden, dass man zu einem wertvollen Azofarbstoff gelangt, wenn man diazotiertes 2-Amino-l-methoxy-4-tertiäramyl- benzol mit 2-Oxynaphtlialin-6,8-disulfonsäure vereinigt.
Der neue Farbstoff bildet ein rotes Pulver, das sich in Wasser mit roter Farbe löst und Wolle aus saurem Bade in gelbstichig roten Tönen färbt.
Das beim vorliegenden Verfahren als Aus gangsstoff dienende 2-Amino-l-methoxy-4- tertiäramylbenzol lässt sich beispielsweise her stellen durch Nitrierung von 1-Oxy-4-tertiär- amylbenzol, Methylierung der Hydroxyl- gruppe und Reduktion des Nitroäthers.
Die Diazotierung kann nach an sich be kannten Methoden zum Beispiel mit Hilfe von Salzsäure und Natriumnitrit durchgeführt werden.
Die Kupplung erfolgt. mit Vorteil in alka lischem Medium.
<I>Beispiel:</I> 7,8 Teile 2-Amino-l-methoxy-4-tertiärainyl- benzolwerden in 70 Teilen Eiswasser und 12 Teilen konzentrierter Salzsäure als Chlor- hydrat gelöst und hierauf unterhalb 50 mit einer konzentrierten Lösung von 2,8 Teilen Natriumnitrit diazotiert.
Der Lösung von 15 Teilen des Dinatrium- salzes der 2-Oxynaplithalin-6,8-disulfonsäure in 200 Teilen Wasser werden noch 10 Teile wasserfreies Nat.riumearbonat zugesetzt, wor auf bei 00 obige Diazolösung eingetragen wird. Die Kupplung findet. nur langsam. statt und wird nach einigen Stunden durch Zusatz von 5 Teilen Natriumhydroxyd beschleunigt. Nach 10 Stunden wird die tiefrote Lösung mit Na triumehlorid versetzt. Der ausfallende rote Farbstoff wird abgesaugt und getrocknet.
Process for the preparation of an azo dye. It has been found that a valuable azo dye is obtained if diazotized 2-amino-1-methoxy-4-tertiaryamylbenzene is combined with 2-oxynaphthalene-6,8-disulfonic acid.
The new dye forms a red powder that dissolves in water with a red color and dyes wool from an acid bath in yellowish red tones.
The 2-amino-1-methoxy-4-tertiary amylbenzene used as starting material in the present process can be produced, for example, by nitration of 1-oxy-4-tertiary amylbenzene, methylation of the hydroxyl group and reduction of the nitro ether.
The diazotization can be carried out by methods known per se, for example with the aid of hydrochloric acid and sodium nitrite.
The coupling takes place. with advantage in alkaline medium.
<I> Example: </I> 7.8 parts of 2-amino-1-methoxy-4-tertiary-arylbenzene are dissolved in 70 parts of ice water and 12 parts of concentrated hydrochloric acid as the chlorohydrate and then below 50 with a concentrated solution of 2 , 8 parts of sodium nitrite diazotized.
10 parts of anhydrous sodium carbonate are added to the solution of 15 parts of the disodium salt of 2-oxynaplithalin-6,8-disulfonic acid in 200 parts of water, and the above diazo solution is added at 00. The clutch takes place. only slowly. instead and is accelerated after a few hours by adding 5 parts of sodium hydroxide. After 10 hours, sodium chloride is added to the deep red solution. The red dye which precipitates is filtered off with suction and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH268075T | 1947-04-30 | ||
| CH262279T | 1947-04-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH268075A true CH268075A (en) | 1950-04-30 |
Family
ID=25730563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH268075D CH268075A (en) | 1947-04-30 | 1947-04-30 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH268075A (en) |
-
1947
- 1947-04-30 CH CH268075D patent/CH268075A/en unknown
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