CH302037A - Process for the preparation of a chromable disazo dye. - Google Patents
Process for the preparation of a chromable disazo dye.Info
- Publication number
- CH302037A CH302037A CH302037DA CH302037A CH 302037 A CH302037 A CH 302037A CH 302037D A CH302037D A CH 302037DA CH 302037 A CH302037 A CH 302037A
- Authority
- CH
- Switzerland
- Prior art keywords
- chromable
- disazo dye
- parts
- preparation
- oxynaphthalene
- 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 4
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- -1 aminomonoazo compound Chemical class 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 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
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- 238000005121 nitriding Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 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 Nr. 297842. Verfahren zur Herstellung eines ehromierbaren Disazofarbatoffes. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines chromier- baren Disazofarbstoffes, welches darin besteht, dass man 1 Mol der Diazoverbindung aus- der durch Kuppeln von diazotiertem Aminobenzol mit Oxybenzol,
anschliessendes Nitrieren des llonoazokörpers und Reduzieren der Nitro- gruppe zur Aminogruppe erhältlichen Amino- monoazoverbindung mit 1. Mol 2-Oxynaph- thalin-4-sulfonsäure kuppelt.
Im nachfolgenden Beispiel bedeuten die Teile Gewichtsteile.
<I>Beispiel:</I> 21,3 Teile der durch Kuppeln von diazo- tiertem Aminobenzol mit Oxybenzol, anschlie ssendes Nitrieren des Monoazokörpers und Reduzieren der Nitrogruppe zur Aminogruppe erhältlichen Aminomonoazoverbindung wer den in 200 Teilen Wasser und 4 Teilen Na triumhydroxyd gelöst. Man versetzt die Lö sung mit 6,9 Teilen Natriumnitrit und tropft sie bei 0-l0 in eine Mischung von 36 Teilen konzentrierter Salzsäure und 100 Teilen Eis wasser.
Den isolierten Diazokörper trägt man unter Eiskühlung in eine Lösung von 22,4 Tei len 2-Oxynaphthalin-4-sulfonsäure und 6 Tei len Natriumhydroxyd in 200 Teilen Wasser und 20 Teilen Pyridin ein. Sobald die Bildung des Disazofarbstoffes beendigt ist, wird dieser mit Natriumchlorid aus der Kupphmgsmasse abgeschieden, abfiltriert und getrocknet.
Der neue chromierbare Disazofarbstoff ist ein dunkles Pulver, das sieh in verdünnter Sodalösung mit violetter, in konzentrierter Schwefelsäure mit grüner Farbe löst und Wolle naehchromiert und metachrom in neu tralen grauen Tönen von vorzüglicher Licht- und guten Nassechtheiten färbt.
<B> Additional patent </B> to the main patent No. 297842. Process for the production of an honorable disazo carbate. The subject matter of the present patent is a process for the preparation of a chromable disazo dye, which consists in that 1 mol of the diazo compound is obtained from the coupling of diazotized aminobenzene with oxybenzene,
subsequent nitration of the ionoazo body and reduction of the nitro group to the amino group of the available amino monoazo compound with 1 mole of 2-oxynaphthalene-4-sulfonic acid.
In the following example, the parts are parts by weight.
<I> Example: </I> 21.3 parts of the aminomonoazo compound obtainable by coupling diazo-tated aminobenzene with oxybenzene, then nitrating the monoazo body and reducing the nitro group to the amino group are dissolved in 200 parts of water and 4 parts of sodium hydroxide. 6.9 parts of sodium nitrite are added to the solution and they are added dropwise to a mixture of 36 parts of concentrated hydrochloric acid and 100 parts of ice water at 0-10.
The isolated diazo body is introduced into a solution of 22.4 parts of 2-oxynaphthalene-4-sulfonic acid and 6 parts of sodium hydroxide in 200 parts of water and 20 parts of pyridine, while cooling with ice. As soon as the formation of the disazo dye has ended, it is separated from the copper with sodium chloride, filtered off and dried.
The new chromable disazo dye is a dark powder that dissolves in a dilute soda solution with a violet color, in concentrated sulfuric acid with a green color, and then chromates wool and dyes it metachromically in neutral gray tones of excellent light and good wet fastness properties.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH302037T | 1951-09-04 | ||
| CH297842T | 1953-01-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH302037A true CH302037A (en) | 1954-09-30 |
Family
ID=25733876
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH302037D CH302037A (en) | 1951-09-04 | 1951-09-04 | Process for the preparation of a chromable disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH302037A (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 |
-
1951
- 1951-09-04 CH CH302037D patent/CH302037A/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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