CH292086A - Process for the preparation of a trisazo dye. - Google Patents
Process for the preparation of a trisazo dye.Info
- Publication number
- CH292086A CH292086A CH292086DA CH292086A CH 292086 A CH292086 A CH 292086A CH 292086D A CH292086D A CH 292086DA CH 292086 A CH292086 A CH 292086A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- orange
- color
- coupling
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 14
- 230000008878 coupling Effects 0.000 claims description 5
- 238000010168 coupling process Methods 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 238000004040 coloring Methods 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
- 239000003086 colorant Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 4
- 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
- 239000000203 mixture Substances 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 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
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-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
- 239000002253 acid Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- -1 amino monoazo Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride 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
- C09B31/16—Trisazo dyes
- C09B31/20—Trisazo dyes from a coupling component"D" containing a directive hydroxyl group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Trisazofarbstoffes. Es wurde gefunden, dass man zu einem wertvollen Trisazofarbstoffgelangt, wenn man
EMI0001.0005
mit 1-Oxybenzol 2-carlbonsäure kuppelt.
Der neue Farbstoff bildet ein orange braunes Pulver, das sich in konzentrierter Schwefelsäure mit. violettblauer und in Wasser mit, oranger Farbe löst und Baumwolle in liehteehten, orangen Tönen färbt, welche gut ätzbar sind. Durch Nachkupfern im gleichen oder in frischem Bade werden die Färbungen etwas kräftiger, aber im Farbton nur wenig verändert. Auch die nachgekupferten Färbun gen sind gut lichtecht und ätzbar und zudem geit waschecht.
Der Aminodisazofarbstoff der obigen For mel kann durch Kuppeln von diazotierter 2 - Aminonaphthalin - 4;8, - disulfonsäiire mit 1 - Amino - 3 - methylbenzol, Diazotieren des Aminomonoazofarbstoffes und nochmaliges
EMI0001.0024
eine Diazoverbindung des Aminodisazofarb- stoffes der Formel Kuppeln mit 1-Amino-3-methylbenzol,
Acylie- ren mit p-Nitrobenzoylchlorid und Reduktion der Nitrogruppe zur Aminogruppe erhalten werden.
Die Diazotierung des Aminodisazofarb- stoffes 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, gewünschten falls unter Zusatz kupplungsbefördernder Mittel wie Pyridin, mit 1-Oxybenzol-2-carbon- säure gekuppelt.
Beispiel: 68,2 Teile des Dinatriumsalzes des Farb stoffes der Formel werden in 1000 Teilen warmem -Wasser gelöst. Zu der auf Zimmertemperatur abgekühlten Lösung gibt man so viel Eis hinzu, dass die Temperatur auf ö sinkt, alsdann 7 Teile Natriumnitrit als 10 /nige Lösung und hierauf unter gutem Rühren auf einmal 2.10 Teile ö /mige Salzsäure.
Man lässt einige Zeit. unter Eiskühlung rühren und vereinigt dann mit einer natriumearbonatalkalischen Lösung von <B>15,2</B> Teilen 1-Oxybenzol-2-earbonsäure. Man lässt unter Kühlung rühren, bis sieh keine Diazoverbindung mehr nachweisen lässt.
Der gebildete Farbstoff ist vollständig ausgefallen; er wird abfiltriert und getrocknet. Zur Er zielung einer besser filtrierbaren Form kann ; das Kupplungsgemiseh auch zuerst aufge wärmt werden, worauf man pro 100 Raumteile Kupplungsgemisch :5 bis 10 Teile Natrium- ehlorid zusetzt.
Process for the preparation of a trisazo dye. A valuable trisazo dye has been found to be obtained by using
EMI0001.0005
couples with 1-oxybenzene-2-carboxylic acid.
The new dye forms an orange-brown powder that dissolves in concentrated sulfuric acid with. violet-blue and dissolves in water with orange paint and dyes cotton in borrowed, orange tones, which are easily etchable. By re-coppering in the same bath or in a fresh bath, the coloring is a little stronger, but only slightly changed in color. The re-coppered colorations are also lightfast and etchable and also washfast.
The amino disazo dye of the above formula can be prepared by coupling diazotized 2 - aminonaphthalene - 4; 8 - disulfonic acid with 1 - amino - 3 - methylbenzene, diazotizing the amino monoazo dye and again
EMI0001.0024
a diazo compound of the amino disazo dye of the formula coupling with 1-amino-3-methylbenzene,
Acylates can be obtained with p-nitrobenzoyl chloride and reduction of the nitro group to the amino group.
The diazotization of the amino disazo dye can be carried out by customary methods known per se, eg. B. with hydrochloric acid and sodium nitrite. The diazodisazo compound thus obtained is then, preferably in an alkaline medium, if desired, if desired with the addition of coupling-promoting agents such as pyridine, coupled with 1-oxybenzene-2-carboxylic acid.
Example: 68.2 parts of the disodium salt of the dye of the formula are dissolved in 1000 parts of warm water. Sufficient ice is added to the solution, which has cooled to room temperature, that the temperature drops to 6, then 7 parts of sodium nitrite as a 10% solution and then, with thorough stirring, 2.10 parts of hydrochloric acid all at once.
One leaves some time. stir while cooling with ice and then combined with an alkaline sodium carbonate solution of 15.2 parts of 1-oxybenzene-2-carboxylic acid. The mixture is stirred with cooling until no more diazo compounds can be detected.
The dye formed has completely precipitated; it is filtered off and dried. In order to achieve a better filterable form; the coupling mixture must also be warmed up first, whereupon 5 to 10 parts of sodium chloride are added per 100 parts by volume of coupling mixture.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH292086T | 1951-09-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH292086A true CH292086A (en) | 1953-07-31 |
Family
ID=4487696
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH292086D CH292086A (en) | 1951-09-05 | 1950-11-02 | Process for the preparation of a trisazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH292086A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2778817A (en) * | 1953-12-24 | 1957-01-22 | Saul & Co | Polyazo dyestuffs |
-
1950
- 1950-11-02 CH CH292086D patent/CH292086A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2778817A (en) * | 1953-12-24 | 1957-01-22 | Saul & Co | Polyazo dyestuffs |
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