CH310697A - Process for the preparation of a water-insoluble monoazo dye. - Google Patents
Process for the preparation of a water-insoluble monoazo dye.Info
- Publication number
- CH310697A CH310697A CH310697DA CH310697A CH 310697 A CH310697 A CH 310697A CH 310697D A CH310697D A CH 310697DA CH 310697 A CH310697 A CH 310697A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- produce
- monoazo dye
- dye
- insoluble monoazo
- Prior art date
Links
- 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 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- 229920000297 Rayon Polymers 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 239000004922 lacquer Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- 239000000049 pigment Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 239000004627 regenerated cellulose Substances 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- HDUINBMMWMTTLC-UHFFFAOYSA-N 3-amino-4-ethoxybenzoic acid Chemical compound CCOC1=CC=C(C(O)=O)C=C1N HDUINBMMWMTTLC-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QMXZSRVFIWACJH-UHFFFAOYSA-N 1-chloro-2,5-dimethoxybenzene Natural products COC1=CC=C(OC)C(Cl)=C1 QMXZSRVFIWACJH-UHFFFAOYSA-N 0.000 description 1
- LWEZLPOWMCXJMG-UHFFFAOYSA-N 3-amino-4-ethoxybenzamide Chemical compound CCOC1=CC=C(C(N)=O)C=C1N LWEZLPOWMCXJMG-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000001875 compounds Chemical class 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
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
- C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines wasserunlöslichen Monoazofarbstoffes. Gegenstand des vorliegenden Zusatz patentes ist ein Verfahren zur Herstellung eines wasserunlöslichen Monoazofarbstoffes, welches dadurch gekennzeichnet ist, dass man die Diazoverbindung aus 1-Anihio-2-äthoxy- benzol-5-carbonsäureamid mit 1-(2',3'-Oxy- naphthoylamino) - 2, 5-dimethoxy-4-chlorben- zol kuppelt.
<I>Beispiel:</I> 9,0 Gewichtsteile 1-Amino-2-äthoxyben- zol-5-carbonsäureamid werden in der üblichen \Weise diazotiert. Hierauf versetzt man die Diazolösung zur Entfernung der überschüssi gen Mineralsäure mit Natriumacetat und rührt sie in eine wässerige Suspension von 17,9 Gewichtsteilen 1-(2',3'-Oxynaphthoyl- amino)-2,5-dimetboxy-4-chlorbenzol ein, die man durch Lösen dieser Verbindung in ver dünnter Natronlauge und Fällen mit Essig säure erhält.
Der beim Erwärmen auf 40 C sich bildende Farbstoff wird nach Beendigung der Kupplung abfiltriert, gut ausgewaschen und getrocknet. Das so erhaltene Produkt stellt ein rotes Pulver dar, das zur Herstellung von Pigment drucken auf Textilien, zur Erzeugung spinn gefärbter Acetatkunstseide und Viskose- kunstseide, zur Herstellung von Farblacken sowie zum Färben von Kondensationsproduk ten aus Formaldehyd und Harnstoff, Pheno- len oder Aminen verwendet werden kann. Auf der pflanzlichen Faser,
einschliesslich regenerierter Cellulose, erzeugt, liefert der Farbstoff lebhafte rote Töne von guter Koch- und Lichtechtheit.
Process for the preparation of a water-insoluble monoazo dye. The subject of the present additional patent is a process for the production of a water-insoluble monoazo dye, which is characterized in that the diazo compound from 1-ani-ani-2-ethoxybenzene-5-carboxamide with 1- (2 ', 3'-oxynaphthoylamino ) - 2, 5-dimethoxy-4-chlorobenzene couples.
<I> Example: </I> 9.0 parts by weight of 1-amino-2-ethoxybenzene-5-carboxamide are diazotized in the usual way. Sodium acetate is then added to the diazo solution to remove the excess mineral acid and it is stirred into an aqueous suspension of 17.9 parts by weight of 1- (2 ', 3'-oxynaphthoylamino) -2,5-dimetboxy-4-chlorobenzene, which is obtained by dissolving this compound in dilute sodium hydroxide solution and cases with acetic acid.
The dye which forms on heating to 40 ° C. is filtered off after the coupling has ended, washed thoroughly and dried. The product obtained in this way is a red powder that is used to produce pigment prints on textiles, to produce spun-dyed acetate and viscose rayon, to produce colored lacquers and to dye condensation products from formaldehyde and urea, phenols or amines can be. On the vegetable fiber,
including regenerated cellulose, the dye provides vivid red tones with good boil and lightfastness.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE310697X | 1951-08-10 | ||
| CH307631T | 1952-08-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH310697A true CH310697A (en) | 1955-10-31 |
Family
ID=25735305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH310697D CH310697A (en) | 1951-08-10 | 1952-08-08 | Process for the preparation of a water-insoluble monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH310697A (en) |
-
1952
- 1952-08-08 CH CH310697D patent/CH310697A/en unknown
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