CH203867A - Process for the preparation of a disazo dye. - Google Patents
Process for the preparation of a disazo dye.Info
- Publication number
- CH203867A CH203867A CH203867DA CH203867A CH 203867 A CH203867 A CH 203867A CH 203867D A CH203867D A CH 203867DA CH 203867 A CH203867 A CH 203867A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- preparation
- disazo dye
- greenish blue
- acid
- Prior art date
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 210000002268 wool Anatomy 0.000 claims description 3
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical class [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 claims description 2
- 239000012670 alkaline solution Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QQSSZTDQUIRFNT-UHFFFAOYSA-N 5-amino-4-methoxy-2-nitrobenzenesulfonic acid Chemical compound COC1=CC([N+]([O-])=O)=C(S(O)(=O)=O)C=C1N QQSSZTDQUIRFNT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 230000002378 acidificating effect Effects 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
- 241001024304 Mino Species 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/04—Disazo dyes characterised by the tetrazo component the tetrazo component being a benzene derivative
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr.<B>199787.</B> Verfahren zur Darstellung eines Disazofarbstoffes. Es wurde gefunden, dass man einen neuen, wertvollen Disazofarbstoff der Formel:
EMI0001.0004
erhält, wenn man den durch Kuppeln von diazotierter 4-Nitro-2-methoxyanilin-5-sul- fonsäure mit Phenol in alkalischer Lösung erhältlichen Monoazofarbstoff reduziert, di- azotiert,
sauer mit 2-Methylamino-8-naph- thol-6-sulfonsäure vereinigt und den Disazo- farbstoff in alkalischer Lösung mit p-Toluol- sulfonsäurechlorid in der phenolischen Hy- droxylgruppe verestert.
Der neue Farbstoff, ein dunkles Pulver, löst sich in Wasser grünstichig blau, in conc. Schwefelsäure violett und färbt Wolle und Seide in grünstichig blauen Tönen.
<I>Beispiel:</I> 24,8 Teile 4-Nitro-2-methoxy-l-amino- benzol-5-sulfonsäure werden diazotiert und mit 9,4 Teilen Phenol sodaalkalisch bei 0 C gekuppelt. Nach vollendeter Kombination er wärmt man auf 45 C und reduziert die Nitrogruppe mit 11,7 Teilen Natriumsulfid während 3 Stunden, versetzt mit Salzsäure -bis zur stark kongosauren Reaktion und fil triert.
Der gebildete Monoazofarbstoff wird mit Hilfe von Soda neutral gelöst, filtriert, mit Salzsäure versetzt, mit Nitrit weiter diazo- tiert und mit einer essigsauren, überschüs siges Natriumaeetat enthaltenden Lösung von 25,3 Teilen 2-Methylamino-8-naphthol-6- sulfonsäure gekuppelt. Alsdann erwärmt man auf<B>60'</B> C, versetzt mit Kochsalz bis zur vollständigen Ausscheidung und filtriert.
Den so erhaltenen, alkaliunechten Disazo- farbstoff unterwirft man in sodaalkalischer Lösung bei 75 C der Veresterung mit 30 bis 40 Teilen p-Toluolsulfonsäurechlorid bis zu erzielter Alkalieehtheit. Der ausgefallene Farbstoff wird filtriert und getrocknet.
Er bildet ein dunkles Pulver, das sich in Wasser mit grünstiehig blauer, in conc.
EMI0002.0009
dadurch gekennzeichnet, dass man den durch Kuppeln von diazotierter 4-Nitro-2-methoxy - anilin-5-sulfonsäure mit Phenol in alkali scher Lösung erhältlichen Monoazofarbstoff reduziert, diazotiert, sauer mit 2-llethyl- a,
mino-$-naphthol-6-sulfonsäure vereinigt und den Disazofarbstoff in alkalischer Lösung Schwefelsäure mit violetter Farbe löst und Wolle und Seide in grünstichig blauen Tönen anfärbt.
Additional patent to main patent no. <B> 199787. </B> Process for the preparation of a disazo dye. It has been found that a new, valuable disazo dye of the formula:
EMI0001.0004
obtained if the monoazo dye obtainable by coupling diazotized 4-nitro-2-methoxyaniline-5-sulphonic acid with phenol in alkaline solution is reduced, diazoated,
combined acidic with 2-methylamino-8-naphthol-6-sulfonic acid and esterified the disazo dye in an alkaline solution with p-toluenesulfonic acid chloride in the phenolic hydroxyl group.
The new dye, a dark powder, dissolves in water with a greenish blue, in conc. Sulfuric acid violet and dyes wool and silk in greenish blue tones.
<I> Example: </I> 24.8 parts of 4-nitro-2-methoxy-1-aminobenzene-5-sulfonic acid are diazotized and coupled with 9.4 parts of phenol in a soda-alkaline manner at 0.degree. When the combination is complete, it is warmed to 45 ° C. and the nitro group is reduced with 11.7 parts of sodium sulfide for 3 hours, mixed with hydrochloric acid until the reaction is strongly Congo acid and filtered.
The monoazo dye formed is dissolved neutrally with the aid of soda, filtered, mixed with hydrochloric acid, further diazo- tated with nitrite and coupled with a solution of 25.3 parts of 2-methylamino-8-naphthol-6-sulfonic acid containing acetic acid, excess sodium acetate . Then it is heated to <B> 60 '</B> C, mixed with common salt until it is completely eliminated and filtered.
The alkali-unfast disazo dye obtained in this way is subjected to esterification in a soda-alkaline solution at 75 ° C. with 30 to 40 parts of p-toluenesulphonic acid chloride until it is alkali-fast. The precipitated dye is filtered off and dried.
It forms a dark powder, which is greenish blue in water, and in conc.
EMI0002.0009
characterized in that the monoazo dye obtainable by coupling diazotized 4-nitro-2-methoxy - aniline-5-sulfonic acid with phenol in an alkaline solution is reduced, diazotized, acidic with 2-llethyl-a,
mino - $ - naphthol-6-sulfonic acid combined and the disazo dye in alkaline solution sulfuric acid dissolves with violet color and dyes wool and silk in greenish blue tones.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH199787T | 1938-07-19 | ||
| CH203867T | 1938-08-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH203867A true CH203867A (en) | 1939-03-31 |
Family
ID=25723358
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH203867D CH203867A (en) | 1938-07-19 | 1938-08-09 | Process for the preparation of a disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH203867A (en) |
-
1938
- 1938-08-09 CH CH203867D patent/CH203867A/en unknown
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