CH220654A - Process for the preparation of a water-insoluble azo dye. - Google Patents
Process for the preparation of a water-insoluble azo dye.Info
- Publication number
- CH220654A CH220654A CH220654DA CH220654A CH 220654 A CH220654 A CH 220654A CH 220654D A CH220654D A CH 220654DA CH 220654 A CH220654 A CH 220654A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- azo dye
- insoluble azo
- preparation
- red
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- RCTGMCJBQGBLKT-PAMTUDGESA-N scarlet red Chemical compound CC1=CC=CC=C1\N=N\C(C=C1C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-PAMTUDGESA-N 0.000 claims description 2
- 229960005369 scarlet red Drugs 0.000 claims description 2
- 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
- RPNOZQWUARYYRS-UHFFFAOYSA-N 1-amino-3-bromoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(Br)C=C2N RPNOZQWUARYYRS-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 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
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines wasserunlöslichen Azofarbstoües. Gegenstand dieses Zusatzpatentes ist ein Verfahren zur Herstellunb eines wa3serunlös- lichen Azofarbstoffes, welches dadurch ge kennzeichnet ist, dass man die Diazoverbin- Jung von 1-Amino-3-bromanthrachinon mit 1-(2'. 3'-Oxynaphthoylamino)-benzol kuppelt.
Der neue Farbstoff bildet ein scharlach rotes Pulver, das sich in konzentrierter Schwe felsäure mit rotvioletter Farbe löst.
<I>Beispiel:</I> 27 Gewichtsteile 1-(2'. 3'-Oxynaphthoyl- amino)-benzo@l werden in verdünnter Natron lauge heiss gelöst, auf Zimmertemperatur ab gekühlt und mit 10g entwässertem Natrium earbonat versetzt.
Hierauf lässt man eine Lö sung von 41 Gewi htsteilen des sauren Di- azoniumsulfates aus 1-Ami#no-3-bromanthra- chinon in Wasser hinzufliessen. Sobald keine Diazoniumverbindung mehr nachweisbar ist, wird filtriert, gewaschen und getrocknet. Man erhält ein scharlachrotes Pulver, das sich in konzentrierter Schwefelsäure mit rotvioletter Farbe löst. Die Kupplung kann auch .in saurem, beispielsweise essigsaurem Medium vorgenommen werden. Ferner kann der Farbstoff auch in Gegenwart von Träger stoffen hergestellt werden.
Er besitzt eine ausgezeichnete Licht-, Öl- und Überspritz- eehtheit.
Process for the production of a water-insoluble azo dye. The subject of this additional patent is a process for the production of a water-insoluble azo dye, which is characterized in that the diazo compound of 1-amino-3-bromoanthraquinone is coupled with 1- (2 ', 3'-oxynaphthoylamino) benzene.
The new dye forms a scarlet red powder that dissolves in concentrated sulfuric acid with a red-violet color.
<I> Example: </I> 27 parts by weight of 1- (2 '. 3'-Oxynaphthoyl-amino) -benzo @ l are dissolved in hot dilute sodium hydroxide solution, cooled to room temperature and treated with 10 g of dehydrated sodium carbonate.
A solution of 41 parts by weight of the acidic diazonium sulfate from 1-amino-3-bromoanthraquinone in water is then allowed to flow in. As soon as no more diazonium compound can be detected, it is filtered, washed and dried. A scarlet powder is obtained which dissolves in concentrated sulfuric acid with a red-violet color. The coupling can also be carried out in an acidic medium, for example acetic acid medium. Furthermore, the dye can also be produced in the presence of a carrier.
It has excellent light, oil and overspray fastness.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH218076T | 1940-06-25 | ||
| DE220654X | 1954-06-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH220654A true CH220654A (en) | 1942-04-15 |
Family
ID=25726100
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH220654D CH220654A (en) | 1940-06-25 | 1940-06-25 | Process for the preparation of a water-insoluble azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH220654A (en) |
-
1940
- 1940-06-25 CH CH220654D patent/CH220654A/en unknown
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