CH296538A - Process for the preparation of a trisazo dye. - Google Patents
Process for the preparation of a trisazo dye.Info
- Publication number
- CH296538A CH296538A CH296538DA CH296538A CH 296538 A CH296538 A CH 296538A CH 296538D A CH296538D A CH 296538DA CH 296538 A CH296538 A CH 296538A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- preparation
- parts
- coupling
- trisazo dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 239000000975 dye Substances 0.000 claims description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- -1 aminomonoazo Chemical group 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 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
- C09B31/16—Trisazo dyes
- C09B31/20—Trisazo dyes from a coupling component"D" containing a directive hydroxyl group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 292086. Verfahren zur Herstellung eines Trisazofarbatoffes. Es wurde gefunden, dass man zu- einem wertvollen Trisazofarbstoff gelangt, wenn man eine Diazoverbindimg des Aminodisazo- farbstoffes der Formel
EMI0001.0009
mit 1-Oxybenzol-2-carbonsäure kuppelt.
Der neue Farbstoff bildet ein rotes Pul ver, das sich in konz. Schwefelsäure mit schwärzlichblauer und in Wasser mit oranger Farbe löst und Baumwolle in lichtechten, orangen Tönen färbt. Die nachgekupferten Färbungen sind zudem gut waschecht.
Der Aminodisazofarbstoff der obigen For mel kann durch Kuppeln von diazotierter 2-Aminonaphthalin-4,8-disulfonsäure mit 1- Amino-2-methoxy-5-methylbenzol, Diazotieren des Aminomonoazofarbstoffes und Kuppeln mit l.-Amino-3-methylbenzol, Acylieren mit p-Nitrobenzoylchlorid und Reduktion der Ni- trogruppe zur Aminogruppe erhalten werden.
Die Diazotierung des Aminodisazofarbstof- fes kann nach üblichen, an sich bekannten Methoden vorgenommen werden, z. B. mit Salzsäure und Natriumnitrit. Die so erhält liche Diazodisazoverbindung wird dann, vor zugsweise in alkalischem Medium, gewünsch- tenfalls unter Zusatz kupplungsfördernder .Mittel, wie Pyridin, mit 1-Oxybenzol-2-car- bonsäure gekuppelt.
<I>Beispiel:</I> 72,2 Teile des Dinatriumsalzes des Farb stoffes der Formel
EMI0001.0039
werden in 2000 Teilen heissem Wasser gelöst. Nach dem Erkalten auf etwa 500 gibt man so viel Eis hinzu, dass die Temperatur auf 5 bis 100 sinkt, und alsdann 7 Teile Natriumnitrit als 10 % ige Lösung. Unter gutem Rühren werden 240 Teile 6 % ige <RTI
ID="0001.0054"> Salzsäure auf ein- mal hinzugefügt. Man lässt einige Zeit unter Kühlung rühren und vereinigt dann mit einer natriumearbonatalkalischen Lösung von 15,2 Teilen 1-Oxybenzol-2-earbonsäure. Zur Be schleunigung der Kupplung können pro 100 Teile Kupplungsgemisch etwa 10 Teile Pyri- din zugesetzt werden.
Der Farbstoff wird nach beendeter Kupplung, gegebenenfalls nachdem das Pyridin abdestilliert wurde, nach Zusatz von etwas Natriumchlorid abfil- triert und getrocknet.
<B> Additional patent </B> to main patent no. 292086. Process for the production of a trisazo carbate. It has been found that a valuable trisazo dye is obtained if one uses a diazo compound of the aminodisazo dye of the formula
EMI0001.0009
with 1-oxybenzene-2-carboxylic acid.
The new dye forms a red powder that is in conc. Sulfuric acid dissolves with blackish blue and in water with orange color and dyes cotton in lightfast, orange tones. The re-coppered colors are also washable.
The amino disazo dye of the above formula can be obtained by coupling diazotized 2-aminonaphthalene-4,8-disulfonic acid with 1-amino-2-methoxy-5-methylbenzene, diazotizing the aminomonoazo dye and coupling with l.-amino-3-methylbenzene, acylating with p-nitrobenzoyl chloride and reduction of the nitro group to the amino group are obtained.
The diazotization of the aminodisazo dye can be carried out by customary methods known per se, eg. B. with hydrochloric acid and sodium nitrite. The diazodisazo compound thus obtainable is then, preferably in an alkaline medium, if desired with the addition of coupling-promoting agents, such as pyridine, coupled with 1-oxybenzene-2-carboxylic acid.
<I> Example: </I> 72.2 parts of the disodium salt of the dye of the formula
EMI0001.0039
are dissolved in 2000 parts of hot water. After cooling to about 500, add enough ice that the temperature drops to 5 to 100, and then 7 parts of sodium nitrite as a 10% solution. 240 parts of 6% RTI are obtained with thorough stirring
ID = "0001.0054"> Hydrochloric acid added all at once. The mixture is stirred for some time with cooling and then combined with an alkaline sodium carbonate solution of 15.2 parts of 1-oxybenzene-2-carboxylic acid. To accelerate the clutch, about 10 parts of pyridine can be added per 100 parts of the clutch mixture.
After the coupling has ended, if appropriate after the pyridine has been distilled off, a little sodium chloride has been added, the dye is filtered off and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH296538T | 1950-11-02 | ||
| CH292086T | 1951-09-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH296538A true CH296538A (en) | 1954-02-15 |
Family
ID=25733187
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH296538D CH296538A (en) | 1950-11-02 | 1950-11-02 | Process for the preparation of a trisazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH296538A (en) |
-
1950
- 1950-11-02 CH CH296538D patent/CH296538A/en unknown
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