CH259332A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH259332A CH259332A CH259332DA CH259332A CH 259332 A CH259332 A CH 259332A CH 259332D A CH259332D A CH 259332DA CH 259332 A CH259332 A CH 259332A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- amino
- azo dye
- preparation
- good
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 239000000987 azo dye Substances 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 229920003043 Cellulose fiber Polymers 0.000 claims description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000001044 red dye Substances 0.000 claims 1
- -1 p-toluenesulfonic acid ester Chemical class 0.000 description 3
- 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 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
- C09B43/14—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents with phosgene or thiophosgene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 253714. Verfahren zur Herstellung eines Azofarbstoffes. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines Azofarbstof- fes. Das Verfahren ist dadurch gekennzeich net, dass man 2 Mol eines Monoa.zofarbstoffes, erhalten durch Diazotieren eines 0-Acylderi- vates der 1-Amino-8-oxy-naphthalin-3,6-disul- fonsäure und Kuppeln der Diazoverbindung mit 1-Amino-3-methyl-6-methoxy-benzol,
und 1 Mol p-Phenylendiamin-carbonsäure mit Phosgen bis zur völligen Umsetzung der Aminogruppen behandelt und den Acylrest abspaltet. Der neue Farbstoff stellt ein dunkles Pulver dar. Er löst sich in Wasser mit roter Farbe und färbt Cellulosefasern in wertvollen klaren Rottönen von sehr guter Lichtechtheit und guten Nassechtheiten.
<I>Beispiel:</I> 62,1 Teile des Monoazofarbstoffes aus diazo- tiertem p-Toluolsulfonsäureester der l-Amino- 8-oxy-naphthalin-3,6-disulfonsäure und 1- Amino-3-methyl-6-methoxy-benzol bzw.
60,7 Teile des entsprechenden Monoazofarbstoffes aus dem Benzolsulfonsäureester der 1-Amino- @-oxy-naphthalin-3,6-disulfonsäure werden zu sammen mit 7.6 Teilen p-Phenylendiamin- carbonsäure in etwa 1600 Teilen Wasser ge löst, dann so lange mit. Phosgen kondensiert, bis in einer Probe die Diazotierbarkeit ver schwunden ist. Hierauf wird mit Ätzalkalien behandelt.
Man erhält nach der Abspaltung der Arylsulfonsä.uregruppe einen Farbstoff, der Cellulosefasern in klaren Rottönen färbt. Sie zeichnen sich wiederum aus durch gute Licht-, Wasch- und Wasserechtheit.
<B> Additional patent </B> to main patent no. 253714. Process for the production of an azo dye. The subject of the present patent is a process for the production of an azo dye. The process is characterized in that 2 moles of a Monoa.zo dye obtained by diazotizing an O-acyl derivative of 1-amino-8-oxynaphthalene-3,6-disulfonic acid and coupling the diazo compound with 1- Amino-3-methyl-6-methoxy-benzene,
and 1 mol of p-phenylenediamine-carboxylic acid is treated with phosgene until the amino groups have reacted completely and the acyl radical is split off. The new dye is a dark powder. It dissolves in water with a red color and dyes cellulose fibers in valuable clear red tones of very good lightfastness and good wetfastness.
<I> Example: </I> 62.1 parts of the monoazo dye from diazo-tated p-toluenesulfonic acid ester of 1-amino-8-oxynaphthalene-3,6-disulfonic acid and 1-amino-3-methyl-6-methoxy -benzene or
60.7 parts of the corresponding monoazo dye from the benzenesulfonic acid ester of 1-amino- @ -oxy-naphthalene-3,6-disulfonic acid are dissolved together with 7.6 parts of p-phenylenediamine carboxylic acid in about 1600 parts of water, then with it. Phosgene condenses until the diazotization has disappeared in a sample. It is then treated with caustic alkalis.
After the arylsulfonic acid group has been split off, a dye is obtained which dyes cellulose fibers in clear red tones. In turn, they are distinguished by good light, washing and water fastness.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH259332T | 1946-10-31 | ||
| CH253714T | 1946-10-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH259332A true CH259332A (en) | 1949-01-15 |
Family
ID=25729790
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH259332D CH259332A (en) | 1946-10-31 | 1946-10-31 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH259332A (en) |
-
1946
- 1946-10-31 CH CH259332D patent/CH259332A/en unknown
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