CH213056A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH213056A CH213056A CH213056DA CH213056A CH 213056 A CH213056 A CH 213056A CH 213056D A CH213056D A CH 213056DA CH 213056 A CH213056 A CH 213056A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- dye
- monoazo dye
- naphthol
- dissolves
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 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 title claims description 3
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- 235000019441 ethanol Nutrition 0.000 claims description 3
- 229920002678 cellulose Polymers 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- 239000004922 lacquer Substances 0.000 claims description 2
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- -1 benzene radical Chemical class 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229940079938 nitrocellulose Drugs 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Nonoazofarbstoffes. Es wurde gefunden, dass man zu wert vollen Pigmentfarbstoffen gelangt, wenn man die Diazoverbindungen aus Aminen von der allgemeinen Formel
EMI0001.0006
worin X die Gruppe -CO- oder -S02- bezeich net, R.1 und Rss Alkyl-, Aralkyl-, Arylreste oder hydroaromatische Reste bedeuten,
die auch miteinander unter Bildung eines hetero- cyelischen Ringsystems verbunden sein kön nen, ferner der Benzolrest a noch durch Alkyl-, Alkogy-, Aralkogy-, Arylogygruppen oder durch Halogen substituiert sein kann,
mit a- oder ss-Naphthol oder deren zur Azo- farbstoffbildung fähigen Halogen- oder Nitro- derivaten kuppelt, wobei beide Farbstoffkom- ponenten keine wasserlöslichmachenden Grup pen, z. B. .Sulfonsäure- oder Carbogylgrup- pen, enthalten sollen.
Die neuen Farbstoffe färben in orangen, roten und braunen Nuancen, die gute Echt heitseigenschaften besitzen. Sie sind unlös lich in Wasser, lösen sich dagegen sehr gut in vielen organischen Lösungsmitteln, wie z. B. Bohlenwaseerstoffen, Alkoholen, Estern, .
Betonen, und können daher auch zum Färben dieser Lösungsmittel sowie damit hergestell- ter Lacke - wie etwa Nitro- oder Acetyl- celluloselacke -, Filme oder Kunstmassen verwendet werden.
Auch zum Färben von Firnislaoken, Kerzen und Fetten sind die Produkte vorzüglich brauchbar. Für die ein zelnen Farbstoffe eignen sich wegen der in ihnen vorhandenen verschiedenartigen .Substi- tuenten die genannten organischen Lösungs- mittel natürlich in unterschiedlicher Weise, doch lassen sich die jeweils .günstigsten Lö- sungsmittel durch einen Versuch leicht er mitteln.
Gegenetand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines Mono- azofarbstoffes, welches dadurch gekennzeich net ist, dass man die Diazoverbindung von 1- Amino-2-methoxybenzol-5-(sulfonyl-N-(n)- butyl-aminobenzol) mit ss-Naphthol kuppelt.
<I>Beispiel:</I> 16,7 Gewichtsteile 1-Amino-2-methoxy- benzol - 5 - (sulfonyl-N-(n)-butyl-aminobenzol) werden in der üblichen Weise diazotiert. Hierauf versetzt man .die Diazolössung zur Bindung .der überschüssigen Mineralsäure mit Natriumacetat und rührt sie in eine Lösung von 7,2 Gewichtsteilen ss-Naphthol in ver dünnter Natronlauge ein.
Nach Beendigung der Kupplung wird der entstandene Farb stoff abfiltriert, gut ausgewaschen und ge trocknet.
Er stellt ein rotes Pulver dar, das sich in Aceton, Athylalkohol und andern orga- nischen Lösungsmitteln leicht mit oranger Farbe löst und Cellulosseesterlacke in lebhaf ten und echten gelbstickig roten Tönen färbt.
Process for the preparation of a nonoazo dye. It has been found that valuable pigment dyes are obtained if the diazo compounds from amines of the general formula
EMI0001.0006
wherein X denotes the group -CO- or -S02-, R.1 and Rss denote alkyl, aralkyl, aryl radicals or hydroaromatic radicals,
which can also be connected to one another to form a heterocyclic ring system, and the benzene radical a can also be substituted by alkyl, alkogy, aralkogy, arylogy groups or by halogen,
with α- or β-naphthol or their halogen or nitro derivatives capable of forming azo dye, both dye components not having any water-solubilizing groups, e.g. B. .Sulfonic acid or Carbogylgrup- should contain.
The new dyes color in orange, red and brown shades, which have good fastness properties. They are insoluble in water, but dissolve very well in many organic solvents, such as. B. Bohlenwaseerstoffen, alcohols, esters,.
Emphasize and can therefore also be used to color these solvents and paints made with them - such as nitro or acetyl cellulose paints -, films or synthetic materials.
The products are also extremely useful for coloring varnish flakes, candles and fats. The organic solvents mentioned are of course suitable in different ways for the individual dyes because of the different types of substituents present in them, but the most favorable solvents in each case can easily be determined by experiment.
Subject of the present patent is a process for the preparation of a monoazo dye, which is characterized in that the diazo compound of 1-amino-2-methoxybenzene-5- (sulfonyl-N- (n) - butyl-aminobenzene) with ss -Naphthol couples.
<I> Example: </I> 16.7 parts by weight of 1-amino-2-methoxybenzene - 5 - (sulfonyl-N- (n) -butyl-aminobenzene) are diazotized in the usual way. Sodium acetate is then added to the diazo solution to bind the excess mineral acid and it is stirred into a solution of 7.2 parts by weight of β-naphthol in dilute sodium hydroxide solution.
After the coupling has ended, the resulting dye is filtered off, washed well and dried.
It is a red powder that dissolves easily with an orange color in acetone, ethyl alcohol and other organic solvents and colors cellulose ester lacquers in vivid and genuine yellowish red tones.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE213056X | 1938-04-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH213056A true CH213056A (en) | 1941-01-15 |
Family
ID=5811258
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH213056D CH213056A (en) | 1938-04-16 | 1939-03-30 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH213056A (en) |
-
1939
- 1939-03-30 CH CH213056D patent/CH213056A/en unknown
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