CH192031A - Process for the preparation of a monoazo dye. - Google Patents
Process for the preparation of a monoazo dye.Info
- Publication number
- CH192031A CH192031A CH192031DA CH192031A CH 192031 A CH192031 A CH 192031A CH 192031D A CH192031D A CH 192031DA CH 192031 A CH192031 A CH 192031A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- monoazo dye
- tetrahydro
- good
- oxynaphthoquinoline
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 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
- 238000002360 preparation method Methods 0.000 title description 3
- 239000000975 dye Substances 0.000 claims description 8
- KZHGPDSVHSDCMX-UHFFFAOYSA-N 6-methoxy-1,3-benzothiazol-2-amine Chemical compound COC1=CC=C2N=C(N)SC2=C1 KZHGPDSVHSDCMX-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 239000003929 acidic solution Substances 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000004744 fabric Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- FOBWEPARRJXYAP-UHFFFAOYSA-N OS(C1C(C=CC2=C3C=CC4=CC=CC=C24)=C3NCC1)(=O)=O Chemical compound OS(C1C(C=CC2=C3C=CC4=CC=CC=C24)=C3NCC1)(=O)=O FOBWEPARRJXYAP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920002678 cellulose Polymers 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
- 239000013078 crystal Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- ACXCKRZOISAYHH-UHFFFAOYSA-N molecular chlorine hydrate Chemical compound O.ClCl ACXCKRZOISAYHH-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines 1VIonoazofarbstoffes. Gegenstand des Hauptpatentes ist ein Verfahren zur Herstellung eines Azo.farb- stoffes, der besonders zum Färben und Drucken von Zelluloseestern ,geeignet ist. Das Verfahren ist dadurch gekennzeichnet, dass mann Py-3-Oxytetrahydro-7-oxynaphtho- ehinolin mit diazotiertem 2-Chlor-4-nitranilin kuppelt.
Es wurde nun gefunden, d:ass man Farb stoffe von ähnlichen Eigenschaften wie dem des I3auptpatentes erhält, wenn mann statt des Py-3-Oxytetrahydro-7-oxynaphthochino- lins das Py-Tetrahydro-7-oxynaphthochinolin mit geeigneten Diazotierungskomponenten vereinigt.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines Mono azofarbstoffes. Das Verfahren ist dadurch gekennzeichnet"dass man 6-Methoxy-2-amino- benzothiazol diazotiert und die Diazoverbin- dung mit Py-Tetrahydro-7-oxynaphthochino- lin in saurer Lösung kuppelt.
Der erhaltene neue Farbstoff färbt Ace- tatseide in ;gut lichtechten, blaugrünen Tönen von .guter Ätzbarkeit.
<I>Beispiel:</I> 18 Gewichtsteile 6-Methoxy-2-aminoben- zothiazol werden in 50%iger Schwefelsäure mit einer konzentrierten wässri;
gen Lösung von 6,9 Gewichtsteilen Natriumnitrit unter halb 0 diazotnert. Die orangegelbe Diazo- lösung läss.t man einfliessen m eine mineral sauer gehaltene wäarige Lösung von 23,;
5 Ge- wichtsteilen Py-@Tetrahydro - 7 - oxynaphtho- chinolinoWorhydrat. Die Kupplung ist in kurzer Zeit beendet. Der in üblicher Weise isolierte Farbstoff färbt Acetateide in gut lichtechten, blaugrünen Tönen von ,guter Ätz- barkeit.
Zur Darstellung des Py-Tetrahydro-7- oxynaphthochinolins kann man wie folgt ver fahren: 50 Gewiohtsteile ;
des Natriumsalzes er a-Naphthochinolin - 7 - sulfosäure (gewonnen durch Einwirkung von Glyzerin, Nitrobenzol und Sühwefelsäure auf 1-Naphthylamin-,5- sulfosäure nach Skraup)
werden in 300 bis 400 Gewichtsteilen Wasser in Gegenwart eines Nickelkatalysators bei 140 bis <B>180'</B> mit Wasserstoff bei einem Druck von 150 Atü hydriert. Nach beendeter Wasserstoffauf nahme lässt man erkalten,
trennt den Kata lysator ab und isoliert die entstandene Tetra- hydronaphthochinolinsulfosäure dureh An- säuern mit Salzsäure und Filtration der aus- gefallenen Säure.
1,00 Gewichtsteile der tetrahydrierten Säure werden mit der vier- bis fünffachen Menge Kaliumhydroxyd. bei 230 bis 240' verschmolzen. Die erkaltete !Schmelze wird in Wasser .gelöst und mit 'Salzsäure neutrali- siert,
wobei das Py-Tetrahydro-7-oxynaphtho- chinolin der wahrscheinlichen Formel:
EMI0002.0047
in Form fast farbloser Kristalle ausfällt. Das in Wasser ziemlich schwer lösliche Chlor hydrat kristallisiert in .gelblichen Blättchen.
Process for the preparation of a 1Vionoazo dye. The main patent relates to a process for the production of an azo dye which is particularly suitable for dyeing and printing cellulose esters. The process is characterized in that Py-3-oxytetrahydro-7-oxynaphtho-ehinoline is coupled with diazotized 2-chloro-4-nitroaniline.
It has now been found that dyes with properties similar to those of the main patent are obtained if, instead of Py-3-oxytetrahydro-7-oxynaphthoquinoline, py-tetrahydro-7-oxynaphthoquinoline is combined with suitable diazotization components.
The present patent is a process for the preparation of a mono azo dye. The process is characterized in that 6-methoxy-2-aminobenzothiazole is diazotized and the diazo compound is coupled with py-tetrahydro-7-oxynaphthoquinoline in acidic solution.
The new dye obtained dyes acetate silk in good lightfast, blue-green tones with good etchability.
<I> Example: </I> 18 parts by weight of 6-methoxy-2-aminobenzothiazole are dissolved in 50% sulfuric acid with a concentrated aqueous solution;
gene solution of 6.9 parts by weight of sodium nitrite below half zero diazotnert. The orange-yellow diazo solution is allowed to flow into a mineral acidic aqueous solution of 23,;
5 parts by weight of Py- @ Tetrahydro - 7 - oxynaphthoquinolino worhydrate. The coupling is completed in a short time. The dye, which is isolated in the customary manner, dyes Acetateide in good lightfast, blue-green shades of good etchability.
To prepare the py-tetrahydro-7-oxynaphthoquinoline you can proceed as follows: 50 parts by weight;
of the sodium salt er a-naphthoquinoline - 7 - sulfonic acid (obtained by the action of glycerine, nitrobenzene and sulfuric acid on 1-naphthylamine, 5-sulfonic acid according to Skraup)
are hydrogenated in 300 to 400 parts by weight of water in the presence of a nickel catalyst at 140 to 180 'with hydrogen at a pressure of 150 atmospheres. After the hydrogen uptake is complete, it is allowed to cool
separates the catalyst and isolates the resulting tetrahydronaphthoquinoline sulfonic acid by acidification with hydrochloric acid and filtration of the precipitated acid.
1.00 parts by weight of the tetrahydrated acid are mixed with four to five times the amount of potassium hydroxide. fused at 230 to 240 '. The cooled! Melt is dissolved in water and neutralized with hydrochloric acid,
where the Py-tetrahydro-7-oxynaphtho-quinoline of the probable formula:
EMI0002.0047
precipitates in the form of almost colorless crystals. The chlorine hydrate, which is rather sparingly soluble in water, crystallizes in yellowish flakes.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE192031X | 1934-11-23 | ||
| CH187427T | 1935-10-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH192031A true CH192031A (en) | 1937-07-15 |
Family
ID=25721526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH192031D CH192031A (en) | 1934-11-23 | 1935-11-19 | Process for the preparation of a monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH192031A (en) |
-
1935
- 1935-11-19 CH CH192031D patent/CH192031A/en unknown
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