CH203866A - Process for the preparation of a disazo dye. - Google Patents
Process for the preparation of a disazo dye.Info
- Publication number
- CH203866A CH203866A CH203866DA CH203866A CH 203866 A CH203866 A CH 203866A CH 203866D A CH203866D A CH 203866DA CH 203866 A CH203866 A CH 203866A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- disazo dye
- acid
- preparation
- sulfonic 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 14
- 239000012670 alkaline solution Substances 0.000 claims description 4
- LTASFWDWBYFZQQ-UHFFFAOYSA-N 2-amino-5-nitrobenzenesulfonic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O LTASFWDWBYFZQQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 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
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 claims description 3
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 claims description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 claims description 2
- 239000003929 acidic solution Substances 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 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 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000003513 alkali 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
- 239000000463 material Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
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
EMI0001.0005
erhält, wenn man den durch Kuppeln von diazotierter 4-Nitro-l-aminobenzol-2-sulfon- säure mit 2-Amino-8-naphthol-6-sulionsäure in saurer Lösung erhältlichen Monoazofarb- stoff reduziert, diazotiert,
alkalisch mit sym. Xylenol vereinigt und den Disazofarbstoff in alkalischer Lösung mit p-Chlorbenzolsulion- säurechlorid in der phenolischen Hydroxyl- gruppe verestert.
Der neue Farbstoff, ein dunkles Pulver, löst sich in Wasser rotviolett, in cone. Schwefelsäure blau und färbt Wolle und Seide in rotstichig violetten Tönen.
<I>Beispiel:</I> <B>21,8</B> Teile 4-Nitro-l-aminobenzol-2-sulfon- säure werden diazotiert und mit 24 Teilen 2-Amino-8-nap'hthol-6-sulfonsä,ure bei<B>0 0 C</B> gekuppelt. Nach vollendeter Kombination er wärmt man auf 45<B>' C</B> und reduziert die Ni- trogruppe mit<B>11,7</B> Teilen Natriumsulfid während<B>3</B> Stunden, versetzt mit Salzsäure bis zur stark kongosauren Reaktion und fil triert.
Der gebildete Monoazolarbstoff wird mit Hilfe von Soda neutral gelöst, filtriert, mit Salzsäure versetzt, mit Nitrit weiter diazo- fiert und mit einer alkalischen Lösung von 12,2 Teilen sym. Xylenol gekuppelt. Als dann erwärmt man auf<B>60 ' C,</B> versetzt mit Kochsalz bis zur vollständigen Ausscheidung und filtriert.
Den so erhaltenen, alkaliunech- ten Disazofarbstoff unterwirft man in soda- alkalischer Lösung bei<B>75 ' C</B> der Vereste- rung mit<B>30</B> bis 40 Teilen p-Chlorbenzol- sulfonsäurechlorid bis zu erzielter Alkali- echtheit. Der ausgefallene Farbstoff wird filtriert und vetrochnet.
21 Er bildet ein dunkles Pulver, das sieh in Wasser mit rot#violetter, in cone. Sehwefel- säure mit blauer Farbe löst und Wolle und Seide in rotstichio- violetten Tönen anfärbt. <B>en</B>
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
EMI0001.0005
obtained when the monoazo dye obtainable in acidic solution by coupling diazotized 4-nitro-1-aminobenzene-2-sulfonic acid with 2-amino-8-naphthol-6-sulfonic acid is reduced, diazotized,
alkaline combined with sym. xylenol and esterified the disazo dye in an alkaline solution with p-chlorobenzenesulionic acid chloride in the phenolic hydroxyl group.
The new dye, a dark powder, dissolves red-violet in water in cone. Sulfuric acid turns blue and dyes wool and silk in reddish purple tones.
<I> Example: </I> <B> 21.8 </B> parts of 4-nitro-1-aminobenzene-2-sulfonic acid are diazotized and 24 parts of 2-amino-8-nap'hthol-6 -sulfonic acid coupled at <B> 0 0 C </B>. After 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 to the strong Congo acid reaction and filtered.
The monoazolar material formed is dissolved neutrally with the aid of soda, filtered, mixed with hydrochloric acid, further diazo- fied with nitrite and coupled with an alkaline solution of 12.2 parts of sym. Xylenol. Then it is heated to <B> 60 ° C, mixed with table salt until it is completely eliminated and filtered.
The alkali-unfast disazo dye obtained in this way is subjected in a soda-alkaline solution at 75 ° C. to esterification with 30 to 40 parts of p-chlorobenzenesulfonic acid chloride up to the level obtained Alkali fastness. The precipitated dye is filtered and processed.
21 It forms a dark powder, which see in water with red # violet, in cone. Sehulphuric acid with a blue color dissolves and dyes wool and silk in reddish-purple tones. <B> en </B>
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH203866T | 1937-05-19 | ||
| CH199787T | 1938-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH203866A true CH203866A (en) | 1939-03-31 |
Family
ID=25723357
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH203866D CH203866A (en) | 1937-05-19 | 1937-05-19 | Process for the preparation of a disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH203866A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994004613A1 (en) * | 1992-08-14 | 1994-03-03 | Zeneca Limited | Watersoluble disazodyes for dyeing leather |
-
1937
- 1937-05-19 CH CH203866D patent/CH203866A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994004613A1 (en) * | 1992-08-14 | 1994-03-03 | Zeneca Limited | Watersoluble disazodyes for dyeing leather |
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