CH259337A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH259337A CH259337A CH259337DA CH259337A CH 259337 A CH259337 A CH 259337A CH 259337D A CH259337D A CH 259337DA CH 259337 A CH259337 A CH 259337A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- amino
- good
- acid
- azo dye
- 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 6
- 229920003043 Cellulose fiber Polymers 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- 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
- HEAHMJLHQCESBZ-UHFFFAOYSA-N 2,5-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(N)C(S(O)(=O)=O)=C1 HEAHMJLHQCESBZ-UHFFFAOYSA-N 0.000 claims 1
- 239000001044 red dye Substances 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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 3
- -1 p-toluenesulphonic acid ester Chemical class 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 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
Zusatzpatent zum Hauptpatent Nr. 258714. Verfahren zur Herstellung eines Azofarbstoffes. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines Azofarb- stoffes. Das Verfahren ist dadurch gekenn zeichnet, dass man 2 Mol eines Monoazofarb- s Stoffes, erhalten durch Diazotieren eines 0- Acylderivatesder 1-Amino-8-oxy-naphthalin- 8,
6-disulfonsäure und Kuppeln der Diazover- bindung mit 1-Amino-3-methyl-6-methoxy- benzol, und 1 Mol p-Phenylendiaminsulfo- i säure mit Phosgen bis zur völligen Umset zung der Aminogruppen behandelt und den Acylrest abspaltet. Der neue Farbstoff stellt ein dunkles Pulver dar.
Er löst sich in Was ser mit roter Farbe und färbt Cellulosefasern in wertvollen klaren Rottönen von sehr guter Lichtechtheit und guten Nasseehtheiten. <I>Beispiel:</I> 62,1 Teile des Monoazofarbstoffes aus dem diazotierten p-Toluolsulfonsäureester der 1-Amino - 8 - oxy - naphtlialin-3,6-disulfonsäure und 1-Amino-3-methyl-6-methoxy-benzol bzw.
60,7 Teile des entsprechenden Monoazofarb- stoffes aus dem Benzolsulfonsäureester der 1-Amino - 8 - oxy - naphthalin-3,6-disulfonsäure werden zusammen mit 9,4 Teilen p-Phenylen- diaminosulfosäure in etwa 720 Teilen Wasser durch Zugabe von Soda gelöst.
Bei schwach lackmussaurer Reaktion vorteilhaft in Gegenwart von Natriumacetat wird hierauf so lange phosgeniert, bis in einer Probe kein primäres Amin mehr nachgewiesex werden kann.
Das Kondensationsprodukt wird mit Kochsalz ausgefällt und filtriert.
Zur Abspaltung der Arylsulfogruppen wird das Kondensationsprodukt in verdünnter ätzalkalischer Lösung auf 80 bis 90 erhitzt.
Der verseifte Farbstoff wird durch Ver setzen mit Kochsalz ausgefällt, abfiltriert und getrocknet. Er färbt Cellulosefasern in klaren Rottönen, die sieh durch gute Licht echtheit sowie gute Wasch- und Wasserecht heit und gute Knitterechtheit auszeichnen.
Additional patent to main patent No. 258714. Process for the production of an azo dye. The present patent is a process for the production of an azo dye. The process is characterized in that 2 moles of a monoazo dye are obtained by diazotizing an 0-acyl derivative of 1-amino-8-oxy-naphthalene-8,
6-disulphonic acid and coupling of the diazo compound with 1-amino-3-methyl-6-methoxybenzene, and 1 mol of p-phenylenediaminesulphonic acid treated with phosgene until the amino groups are completely converted 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 with very good lightfastness and good wetness properties. <I> Example: </I> 62.1 parts of the monoazo dye from the diazotized p-toluenesulphonic acid ester of 1-amino-8-oxy-naphthalen-3,6-disulphonic 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-8-oxynaphthalene-3,6-disulfonic acid are dissolved together with 9.4 parts of p-phenylenediamino sulfonic acid in about 720 parts of water by adding soda .
In the case of a weak lacquer acid reaction, advantageously in the presence of sodium acetate, phosgenation is then carried out until no primary amine can be detected in a sample.
The condensation product is precipitated with common salt and filtered.
To split off the aryl sulfo groups, the condensation product is heated to 80 to 90 in a dilute caustic solution.
The saponified dye is precipitated by setting with sodium chloride, filtered off and dried. It dyes cellulose fibers in clear red tones, which are characterized by good lightfastness as well as good washing and waterfastness and good crease resistance.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH259337T | 1946-10-31 | ||
| CH253714T | 1946-10-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH259337A true CH259337A (en) | 1949-01-15 |
Family
ID=25729795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH259337D CH259337A (en) | 1946-10-31 | 1946-10-31 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH259337A (en) |
-
1946
- 1946-10-31 CH CH259337D patent/CH259337A/en unknown
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