CH203865A - Process for the preparation of a disazo dye. - Google Patents
Process for the preparation of a disazo dye.Info
- Publication number
- CH203865A CH203865A CH203865DA CH203865A CH 203865 A CH203865 A CH 203865A CH 203865D A CH203865D A CH 203865DA CH 203865 A CH203865 A CH 203865A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- disazo dye
- preparation
- sulfonic acid
- dianotated
- 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
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims description 6
- 239000012670 alkaline solution Substances 0.000 claims description 4
- 239000003929 acidic solution Substances 0.000 claims 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 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 210000002268 wool Anatomy 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 241000738824 Hottonia palustris Species 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 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 description 1
- 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 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- MCQQMNLUXQSWPL-UHFFFAOYSA-N NC(C1S(O)(=O)=O)=CC=CC1=[N+]=[N-] Chemical compound NC(C1S(O)(=O)=O)=CC=CC1=[N+]=[N-] MCQQMNLUXQSWPL-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
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 210000000988 bone and bone Anatomy 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
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
<B>Zusatzpatent</B> zum Hauptpatent N r. 199787. Verfahren zur Darstellung eines Disazofarbstoffes. Es wurde gefunden, dass man einen neuen, wertvollen Disazofarbstoff der Formel
EMI0001.0003
erhält, wenn man den durch Kuppeln von di- azotierter 4-Nitro-l-aminobenzol-2-sulfon- säure mit 2-Amino-8-naphthol-6-sulfonsäure in saurer Lösung erhältlichen Monoazofarb- stoff reduziert, diazotiert,
'alkalisch mit m- Kresol vereinigt und den Disazofarbstoff in alkalischer Lösung mit p-Toluolsulfonsäure- chlorid in der phenolischen Hydroxylgruppe verestert.
Der neue Farbstoff, ein dunkles Pulver, löst sich in Wasser violett, in cone. Schwe felsäure blau und färbt Wolle und Seide in echten violetten Tönen.
<I>Beispiel:</I> 21,8 Teile 4-Nitro-l-aminobenzol-2-sul- fonsKure werden diazotiert und mit 24 Teilen 2-Amino-8-naphthol-6-sulfonsäure in saurer Lösung bei 0 C gekuppelt. Nach vollen deter Kombination erwärmt man auf 45 C und reduziert die Nitrogruppe mit<B>11,7</B> Tei len Natriumsulfid während 3 Stunden, ver setzt mit Salzsäure bis zur stark kongosauren Reaktion und filtriert.
Der gebildete Monoazofarbstoff wird mit Hilfe von Soda neutral gelöst, filtriert, mit Salzsäure versetzt, mit Nitrit weiter diazo- tiert und mit einer alkalischen Lösung von <B>10,8</B> Teilen m-Kresol gekuppelt. Alsdann er wärmt man auf 60 C, versetzt mit Koch salz bis zur vollständigen Ausscheidung und filtriert.
Den so erhaltenen, alkaliunechten Disazofarbstoff unterwirft man in solo alkalischer Lösung bei 75 C der Veresterung mit 30 bis 40 Teilen p-Toliiolsiilfonsäure- chlorid bis zu erzielter Alkalieehtheit. Der ausgefallene Farbstoff wird filtriert und ge trocknet.
Er bildet ein dunkles Pulver, das sich in Wasser mit violetter, in Bone. Sebivefelsdiizre mit 'blauer Farbe löst und Wolle und Seide in echten violetten Tönen anfärbt.
<B> Additional patent </B> to main patent no. 199787. Method for the preparation of a disazo dye. It has been found that a new, valuable disazo dye of the formula
EMI0001.0003
obtained if the monoazo dye obtainable in acidic solution by coupling diazo-l-aminobenzene-2-sulfonic acid with 2-amino-8-naphthol-6-sulfonic acid is reduced, diazotized,
'Combined alkaline with m-cresol and esterified the disazo dye in alkaline solution with p-toluenesulfonic acid chloride in the phenolic hydroxyl group.
The new dye, a dark powder, dissolves violet in water, in cone. Sulfur acid blue and dyes wool and silk in real violet tones.
<I> Example: </I> 21.8 parts of 4-nitro-1-aminobenzene-2-sulphonic acid are diazotized and coupled with 24 parts of 2-amino-8-naphthol-6-sulphonic acid in acidic solution at 0.degree . When the combination is complete, the mixture is heated 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 acidic and filtered.
The monoazo dye formed is dissolved neutrally with the aid of soda, filtered, mixed with hydrochloric acid, further diazotized with nitrite and coupled with an alkaline solution of 10.8 parts of m-cresol. Then it is warmed to 60 C, mixed with sodium chloride until it is completely eliminated and filtered.
The disazo dye obtained in this way, which is not resistant to alkali, is subjected in a solo alkaline solution at 75 ° C. to esterification with 30 to 40 parts of p-toliolsilfonic acid chloride until it is alkali-fast. The precipitated dye is filtered and dried.
It forms a dark powder that turns purple in water, in bone. Sebivefelsdiizre with 'blue color dissolves and dyes wool and silk in real violet tones.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH203865T | 1937-05-19 | ||
| CH199787T | 1938-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH203865A true CH203865A (en) | 1939-03-31 |
Family
ID=25723356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH203865D CH203865A (en) | 1937-05-19 | 1937-05-19 | Process for the preparation of a disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH203865A (en) |
-
1937
- 1937-05-19 CH CH203865D patent/CH203865A/en unknown
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