CH259721A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH259721A CH259721A CH259721DA CH259721A CH 259721 A CH259721 A CH 259721A CH 259721D A CH259721D A CH 259721DA CH 259721 A CH259721 A CH 259721A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- monoazo dye
- preparation
- dye
- parts
- Prior art date
Links
- 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 claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RZKKOBGFCAHLCZ-UHFFFAOYSA-N 1,4-dichloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1Cl RZKKOBGFCAHLCZ-UHFFFAOYSA-N 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
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
-
- 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
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/28—Amino naphthols
- C09B29/30—Amino naphtholsulfonic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Monoazofarbstoffes. Es wurde gefunden, dass man zu einem wertvollen Monoazofarbstoff gelangt, wenn man dianotierten 4,2'-Dichlor-2-amino-1,1'- diphenyläther in saurem Medium mit 2-Amino- rtaphthalin-6-sulfonsäure vereinigt.
Der neue Farbstoff stellt in trockenem Zustand ein rotes Pulver dar, das Wolle aus saurem Bade in klaren, orangen Tönen von guten Nasseclitheiten und guter Liehteehtheit ,färbt.
Der als Ausgangsstoff verwendete 4,2'-Di- chlor-2-amino-1,1'-diphenyläther kann z. B. nach an sich bekannter Methode durch Um setzen von 2-Nitro-1,4-dichlorbenzol mit einem Alkalisalz des 2-Chlor-l-o-,ybenzols und an schliessende Reduktion der Nitrogruppe zur Aminogruppe hergestellt werden. Die Diano tierung des 4,2'-Dichlor-2-amino-1,1'-diplienyl- äthers geschieht in üblicher, an sich bekann ter Weise.
Die Kupplung des dianotierten 4,2'-Di- ehlor-2-amino-l,l'-diphenyläthers erfolgt in saurem, beispielsweise mineralsaurem Medium. (lewünsehtenfalls kann die überschüssige Mi neralsäure in an sich bekannter Weise, z. B. < furch Zusatz von Natriumaeetat, abgestumpft werden.
Beispiel: 25,4 Teile 4,2'-Diehlor-2-amino-1,1'-di- phenyläther werden mit 25 Teilen 30 % iger Salzsäure und 6,9 Teilen Natriumnitrit in 200 Teilen Wasser bei 0 bis 5 in üblicher -'iTeise dianotiert. Die klare Diazoniumlösung lässt man bei 0 bis 5 zu einer neutralen Lö sung von 24,5 Teilen des Natriumsalzes der 2-.Aminonaphthalin-6-sttlfonsäure in 300 Teilen Wasser fliessen.
Durch Zutropf en von 10 % iger N atriumcarbonatlösung wird die überschüssige Salzsäure so weit neutralisiert, da.ss das Kupp lungsgemisch stets nur schwach mineralsaure Reaktion anzeigt. Nach 12 Stunden lässt man die Temperatur auf 10 bis 15 ansteigen und rührt weitere 12 Stunden bei dieser Tempera tur. Nach dieser Zeit ist die Diazoniumver- bindung verschwunden.
Man erwärmt nun auf 40 bis 50 , setzt. so viel Natriumcarbonat hinzu, dass die Lösung deutlich alkalisch re agiert, filtriert nach Zusatz von 30 Teilen Na- triunichlorid den gebildeten Farbstoff ab und trocknet ihn.
Process for the preparation of a monoazo dye. It has been found that a valuable monoazo dye is obtained if dianotated 4,2'-dichloro-2-amino-1,1'-diphenyl ether is combined with 2-amino-rtaphthalene-6-sulfonic acid in an acidic medium.
When dry, the new dye is a red powder that dyes wool from an acid bath in clear, orange tones of good wetness and good lightness.
The 4,2'-dichloro-2-amino-1,1'-diphenyl ether used as starting material can, for. B. by a method known per se by order of 2-nitro-1,4-dichlorobenzene with an alkali salt of 2-chloro-l-o-, ybenzene and subsequent reduction of the nitro group to the amino group. The dianation of the 4,2'-dichloro-2-amino-1,1'-diplienyl ether takes place in the usual, per se known manner.
The coupling of the dianotized 4,2'-dichloro-2-amino-1,1'-diphenyl ether takes place in an acidic medium, for example a mineral acid medium. (If necessary, the excess mineral acid can be blunted in a manner known per se, e.g. by adding sodium acetate.
Example: 25.4 parts of 4,2'-Diehlor-2-amino-1,1'-diphenyl ether are mixed with 25 parts of 30% hydrochloric acid and 6.9 parts of sodium nitrite in 200 parts of water at 0 to 5 in the usual way - 'iTeise dianotiert. The clear diazonium solution is allowed to flow at 0 to 5 to a neutral solution of 24.5 parts of the sodium salt of 2-aminonaphthalene-6-sttlfonic acid in 300 parts of water.
By adding 10% strength sodium carbonate solution dropwise, the excess hydrochloric acid is neutralized to such an extent that the coupling mixture always shows only a weak mineral acid reaction. After 12 hours, the temperature is allowed to rise to 10 to 15 and the mixture is stirred for a further 12 hours at this temperature. After this time the diazonium compound has disappeared.
It is now heated to 40 to 50, sets. so much sodium carbonate is added that the solution reacts clearly alkaline, after the addition of 30 parts of sodium triunichloride, the dye formed is filtered off and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH254805T | 1945-10-04 | ||
| CH259721T | 1945-10-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH259721A true CH259721A (en) | 1949-01-31 |
Family
ID=25729857
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH259721D CH259721A (en) | 1945-10-04 | 1945-10-04 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH259721A (en) |
-
1945
- 1945-10-04 CH CH259721D patent/CH259721A/en unknown
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