DE200115C - - Google Patents
Info
- Publication number
- DE200115C DE200115C DE1907200115D DE200115DA DE200115C DE 200115 C DE200115 C DE 200115C DE 1907200115 D DE1907200115 D DE 1907200115D DE 200115D A DE200115D A DE 200115DA DE 200115 C DE200115 C DE 200115C
- Authority
- DE
- Germany
- Prior art keywords
- aminonaphthol
- parts
- coupling
- solution
- diazotized
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 230000001808 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 150000008049 diazo compounds Chemical class 0.000 description 6
- -1 8-aminonaphthol sulfonic acids Chemical class 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HMNPDEGBVWDHAR-UHFFFAOYSA-N 8-aminonaphthalen-1-ol Chemical compound C1=CC(O)=C2C(N)=CC=CC2=C1 HMNPDEGBVWDHAR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 241000490025 Schefflera digitata Species 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N ethanone Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- 230000000415 inactivating Effects 0.000 description 1
- 235000015250 liver sausages Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007787 solid 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/08—Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
Patentiert im Deutschen Reiche vom 23. April 1907 ab. Längste Dauer: 10. Dezember 1921.Patented in the German Empire on April 23, 1907. Longest duration: December 10, 1921.
Durch Patent 199175 ist ein Verfahren zur Darstellung von sekundären Disazofarbstoffen mit Hilfe der Diazoverbindungen der Schwefligsäureester des ι · 8-Aminonaphtols oder der ι · 8-Aminonaphtolsulfosäuren geschützt. Es ist dort erwähnt worden, daß diese Arbeitsweise vor der Verwendung der Diazoverbindungen selbst den Vorteil bietet, daß durch die Inaktivierung der Hydroxylgruppe in denBy patent 199175 is a method for Preparation of secondary disazo dyes with the help of the diazo compounds of the sulfurous acid esters of ι · 8-aminonaphthol or ι · 8-aminonaphthol sulfonic acids. It it has been mentioned there that this procedure prior to the use of the diazo compounds itself has the advantage that by inactivating the hydroxyl group in the
ίο Diazonaphtolsulfosäuren Nebenreaktionen bei der Kuppelung mit den Mittelkomponenten leichter vermieden werden können.ίο Diazonaphthol sulfonic acids cause side reactions the coupling with the central components can be avoided more easily.
Es wurde nun gefunden, daß man diese günstige Wirkung auch dadurch erzielen kann, daß man statt der diazotierten Schwefligsäureester die diazotierten Acetylverbindungen des 1 ·8-Aminonaphtols oder der ι ·8-Aminonaphtolsulfosäuren verwendet.It has now been found that this beneficial effect can also be achieved in this way can that instead of the diazotized sulfurous acid esters, the diazotized acetyl compounds of the 1 · 8-aminonaphthol or the ι · 8-aminonaphthol sulfonic acids used.
Die aus 319 Teilen ι ·8- Aminonaphtol-3 -6-disulfosäure durch Behandeln ihrer Diazoverbindung mit Essigsäureanhydrid erhältliche, in der Hydroxylgruppe acetylierte Diazoverbindung wird bei 5 bis io° mit einer wässerigen Lösung von 225 Teilen a-Naphtylaminchlorhydrat vereinigt. Zur Beendigung der Kuppelung fügt man eine Lösung von 170 Teilen kristallisiertem Natriumacetat hinzu und filtriert das entstandene Zwischenprodukt ab. Das abfiltrierte Zwischenprodukt wird mit wässeriger Sodalösung in Lösung gebracht, mit 350 Teilen Salzsäure von 190 Be. angesäuert, auf o° abgekühlt und mit 69 Teilen Natriumnitrit diazotiert. Die Diazoverbindung gibt man zu einer Lösung von 315 Teilen 2-Phenylamino-5-naphtol-7-sulfosäure in so viel Ammoniak, daß die, Reaktion bis zur Beendigung der Kuppelung alkalisch bleibt. Die fertige Kuppelung wird 1 Stunde lang unter Zusatz von 200 Teilen festem Ätznatron auf eine Temperatur von 900 erwärmt und erkalten gelassen. Der Farbstoff kristallisiert größtenteils aus, der Rest läßt sich durch Aussalzen gewinnen.The diazo compound acetylated in the hydroxyl group, obtainable from 319 parts of ι · 8-aminonaphthol-3-6-disulfonic acid by treating its diazo compound with acetic anhydride, is combined at 5 to 10 ° with an aqueous solution of 225 parts of a-naphthylamine chlorohydrate. To terminate the coupling, a solution of 170 parts of crystallized sodium acetate is added and the intermediate product formed is filtered off. The filtered intermediate product is brought into solution with aqueous soda solution, with 350 parts of hydrochloric acid of 19 0 Be. acidified, cooled to 0 ° and diazotized with 69 parts of sodium nitrite. The diazo compound is added to a solution of 315 parts of 2-phenylamino-5-naphthol-7-sulfonic acid in so much ammonia that the reaction remains alkaline until the coupling is complete. The finished coupling is heated to a temperature of 90 0 for 1 hour with the addition of 200 parts of solid caustic soda and allowed to cool. Most of the dye crystallizes out, the rest can be obtained by salting out.
Der Farbstoff ist identisch mit dem in Beispiel 1 des Patents 198102 beschriebenen Produkt.The dye is identical to that described in Example 1 of Patent 198102 Product.
Pate ν t-An SPRu c η :Pate ν t-An SPRu c η:
Abänderung des durch Patent 199175, Zusatz zum Patent 198102, geschützten Verfahrens zur Darstellung von sekundären Disazofarbstoffen, darin bestehend, daß man statt der diazotierten Schwefligsäureester des 1 «8-Aminonaphtols oder der ι · 8- Aminonaphtolsulfosäuren hier die acetylierten Diazoverbindungen der genannten Körper verwendet, und den Acetylrest entweder nach erfolgter Kuppelung mit den Mittelkomponenten aus den Zwischenprodukten oder erst nach weiterer Kuppelung mit den Endkomponenten aus den fertigen Disazofarbstoffen abspaltet.Modification of that protected by patent 199175, addition to patent 198102 Process for the preparation of secondary disazo dyes, consisting therein that instead of the diazotized sulfurous acid ester of 1 «8-aminonaphthol or of the ι · 8- aminonaphthol sulfonic acids here are the acetylated diazo compounds of the above Body used, and the acetyl radical either after coupling with the middle components from the intermediate products or only split off from the finished disazo dyes after further coupling with the end components.
BERLIN. GEDRUCKT IN DER REICHSDRUCKEREI.BERLIN. PRINTED IN THE REICHSDRUCKEREI.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT39017D AT39017B (en) | 1907-04-22 | 1908-07-13 | Process for the preparation of secondary disazo dyes. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE200115C true DE200115C (en) |
Family
ID=462777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1907200115D Expired - Lifetime DE200115C (en) | 1907-04-22 | 1907-04-22 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE200115C (en) |
-
1907
- 1907-04-22 DE DE1907200115D patent/DE200115C/de not_active Expired - Lifetime
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