DE264288C - - Google Patents
Info
- Publication number
- DE264288C DE264288C DENDAT264288D DE264288DA DE264288C DE 264288 C DE264288 C DE 264288C DE NDAT264288 D DENDAT264288 D DE NDAT264288D DE 264288D A DE264288D A DE 264288DA DE 264288 C DE264288 C DE 264288C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- acetoacetic ester
- dyes
- preparation
- ether sulfonic
- 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.)
- Active
Links
- 239000000975 dye Substances 0.000 claims description 7
- XYIBRDXRRQCHLP-UHFFFAOYSA-N Ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 210000002268 Wool Anatomy 0.000 claims description 3
- 239000000543 intermediate Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- -1 diazodiphenyl ether sulfonic acids Chemical class 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
- NMFFUUFPJJOWHK-UHFFFAOYSA-N 2-phenoxyaniline Chemical compound NC1=CC=CC=C1OC1=CC=CC=C1 NMFFUUFPJJOWHK-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 241000947840 Alteromonadales Species 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- LMTXFKUGOAPNQP-UHFFFAOYSA-N phenoxazin-10-ium-10-ylideneazanide Chemical compound C1=CC=C2[N+](=[N-])C3=CC=CC=C3OC2=C1 LMTXFKUGOAPNQP-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/003—Cyclisation of azo dyes; Condensation of azo dyes with formation of ring, e.g. of azopyrazolone dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Coloring (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- JVi 264288 KLASSE 22 a. GRUPPE- JVi 264288 CLASS 22 a. GROUP
Verfahren zur Darstellung gelber Wollfarbstoffe. Zusatz zum Patent 264287.Process for the preparation of yellow wool dyes. Addendum to patent 264287.
Patentiert im Deutschen Reiche vom 19. September 1912 ab. Längste Dauer: 22. August 1927.Patented in the German Empire on September 19, 1912. Longest duration: August 22, 1927.
' Durch Patent 264287 ist ein Verfahren zur Darstellung von gelben Wollfarbstoffen geschützt, das darin besteht, daß man 2 Moleküle einer Diazodiphenyläthersulfosäure oder deren Substitutionsprodukte mit 1 Molekül eines Dipyrazolons der allgemeinen Formel'' Patent 264287 protects a process for the preparation of yellow wool dyes, that consists in adding 2 molecules of a diazodiphenyl ether sulfonic acid or its substitution products with 1 molecule of a dipyrazolone of the general formula
C ff,C ff,
CH3 CH 3
H.C--H.C--
-CH2,-CH 2 ,
worin X einen aromatischen Rest bedeutet, kombiniert.wherein X is an aromatic radical, combined.
Es wurde nun gefunden, daß man zu den gleichen Farbstoffen gelangt, wenn man Diazodiphenyläthersulfosäuren mit Acetessigester kuppelt und die so erhaltenen Produkte mit Dihydrazinen kondensiert. Man umgeht so die Darstellung der Dipyrazolone und gewinnt die Farbstoffe direkt in sehr reiner Form.It has now been found that the same dyes are obtained if diazodiphenyl ether sulfonic acids are used with acetoacetic ester and the products thus obtained are condensed with dihydrazines. This is how you deal with it the representation of the Dipyrazolone and wins the dyes directly in a very pure form.
Verwendet man die im Beispiel des Hauptpatents genannte 2-Aminodiphenyläthersulfosäure, so erhält man durch Kombination ihrer Diazoverbindung mit Acetessigester ein Zwischenprodukt, das als Natriumsalz schwach gelb gefärbte Blättchen bildet und sich in Wasser, ebenso in konzentrierter Schwefelsäure, mit grünlichgelber Farbe löst. Im allgemeinen ist es nicht erforderlich, die Zwischenprodukte zu isolieren.If the 2-aminodiphenyl ether sulfonic acid mentioned in the example of the main patent is used, by combining their diazo compound with acetoacetic ester, an intermediate product is obtained, the pale yellow colored leaflet forms as the sodium salt and dissolves in water as well as in concentrated sulfuric acid, dissolves with greenish yellow color. In general it is not necessary to use the intermediates to isolate.
53 Teile der durch Sulfieren des 2-Aminodiphenyläthers erhaltenen Sulfosäure werden mit 14 Teilen Natriumnitrit und 100 Teilen Salzsäure 12 ° Be. diazotiert. Zu der Diazoverbindung gibt man unter Rühren 27 Teile Acetessigester und 33 Teile kalzinierte Soda. Nach beendeter Kombination säuert man schwach an, fügt 32,8 Teile salzsaures 4,4'-Dihydrazino-3,3'-dimethyldiphenylmethan hinzu und wärmt an. Die Kondensation ist in kurzer Zeit beendet. Der Farbstoff wird in das Natriumsalz übergeführt und isoliert. Er ist identisch mit dem nach dem Beispiel des Hauptpatents hergestellten Farbstoff.53 parts of the sulfonation of 2-aminodiphenyl ether The sulfonic acid obtained is mixed with 14 parts of sodium nitrite and 100 parts Hydrochloric acid 12 ° Be. diazotized. 27 parts are added to the diazo compound with stirring Acetoacetic ester and 33 parts calcined soda. When the combination is complete, acidify weakly, adds 32.8 parts of 4,4'-dihydrazino-3,3'-dimethyldiphenylmethane hydrochloric acid added and warms up. The condensation ends in a short time. The dye is in the sodium salt converted and isolated. It is identical to that according to the example of Main patent made dye.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE264288C true DE264288C (en) |
Family
ID=521614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT264288D Active DE264288C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE264288C (en) |
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- DE DENDAT264288D patent/DE264288C/de active Active
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