CH311042A - Process for the preparation of a yellow monoazo dye. - Google Patents
Process for the preparation of a yellow monoazo dye.Info
- Publication number
- CH311042A CH311042A CH311042DA CH311042A CH 311042 A CH311042 A CH 311042A CH 311042D A CH311042D A CH 311042DA CH 311042 A CH311042 A CH 311042A
- Authority
- CH
- Switzerland
- Prior art keywords
- monoazo dye
- yellow
- acid
- preparation
- dye
- 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 10
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 6
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- 230000007935 neutral effect Effects 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 210000002268 wool Anatomy 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- UWLNKHDLVZEYKQ-UHFFFAOYSA-N 4-chloro-3-(3-methyl-5-oxo-4h-pyrazol-1-yl)benzenesulfonic acid Chemical compound O=C1CC(C)=NN1C1=CC(S(O)(=O)=O)=CC=C1Cl UWLNKHDLVZEYKQ-UHFFFAOYSA-N 0.000 claims description 2
- 241000283153 Cetacea Species 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000013535 sea water Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004040 coloring Methods 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
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 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
- C09B43/30—Preparation of azo dyes from other azo compounds by esterification of —COOH or —SO3H groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 304389. Verfahren zur Herstellung eines gelben Monoazofarbstoffes. CTegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines gelben Mono azofarbstoffes. Das Verfahren ist dadurch ge kennzeichnet, dass man die Diazov erbindung der Anthranilsäure mit 1-(2'-Chlor-5'-sulfo- hhenyl)-3-methyl-5-pyrazolon vereinigt,
den erhaltenen Monoazofarbstoff mit Thionylchlo- rid in das Säurechlorid umwandelt und dieses auf Decylalkohol einwirken lässt.
Der erhaltene neue Monoazofarbstoff der Formel
EMI0001.0013
stellt ein gelbes Pulver dar. Er löst sich in warmem Wasser und in konzentrierter Schwe felsäure mit grünstichig gelber Farbe. Wolle wird aus neutralem bis schwach saurem Bade in klaren, grünstiehig gelben Tönen gefärbt. Die Färbung ist sehr gut licht-, walk- und seewassereeht.
Beispiel: Die Diazoverbindung von 13,7 Teilen An- thranilsäure wird mit 28,85 Teilen 1-(2'- Chlor-5'-sulfo-phenyl)-3-methyl-5-pyrazolon in lackmusneutralem Medium gekuppelt.
Nach beendeter Kupplung wird die Farbstofflösung mit 15 Teilen 30o/niger Salzsäure versetzt, die ausgeschiedene, freie Farbstoffsäure abfil- triert, mit angesäuerter 2o/oiger Natriumchlo- ridlösung gewaschen und getrocknet. Der so . erhaltene Monoazofarbstoff wird in 300 Teile Thionylchlorid eingetragen und diese Suspen sion während 48 Stunden unter Rühren auf 35-45 gehalten.
Das überschüssige Thionyl- chlorid wird dann im Vakuum vollständig abdestilliert, das Reaktionsprodukt in 160 Tei len Benzol angeschlämmt, mit 15,8 Teilen De- canol versetzt und während 24 Stunden auf 60-65 gehalten. Man entfernt das Benzol mittels Wasserdampf, salzt den erhaltenen Monoazofarbstoff der Formel
EMI0001.0047
aus der sodaalkalisch gestellten Lösung mit Kaliumchlorid aus, filtriert ihn ab, wäscht und trocknet ihn.
Der Farbstoff stellt ein gelbes Pulver dar. Er löst sich in warmem Wasser und in kon zentrierter Schwefelsäure mit grünstichig gel ber Farbe. Wolle wird aus neutralem bis schwach saurem Bade in klaren, grünstichig gelben Tönen gefärbt. Die Färbung ist sehr gut licht-, walk- und seewasserecht.
<B> Additional patent </B> to main patent no. 304389. Process for the production of a yellow monoazo dye. The subject of the present patent is a process for the preparation of a yellow mono azo dye. The process is characterized in that the diazo compound of anthranilic acid is combined with 1- (2'-chloro-5'-sulfohhenyl) -3-methyl-5-pyrazolone,
the monoazo dye obtained is converted into the acid chloride with thionyl chloride and this is allowed to act on decyl alcohol.
The resulting new monoazo dye of the formula
EMI0001.0013
represents a yellow powder. It dissolves in warm water and in concentrated sulfuric acid with a greenish yellow color. Wool is dyed from neutral to slightly acidic bath in clear, greenish yellow tones. The color is very light, whale and sea water.
Example: The diazo compound of 13.7 parts of anthanilic acid is coupled with 28.85 parts of 1- (2'-chloro-5'-sulfo-phenyl) -3-methyl-5-pyrazolone in a litmus-neutral medium.
When the coupling is complete, 15 parts of 30% hydrochloric acid are added to the dye solution, and the free dye acid which has separated out is filtered off, washed with acidified 20% sodium chloride solution and dried. The so. The monoazo dye obtained is introduced into 300 parts of thionyl chloride and this suspension is kept at 35-45 for 48 hours with stirring.
The excess thionyl chloride is then completely distilled off in vacuo, the reaction product is suspended in 160 parts of benzene, mixed with 15.8 parts of decanol and kept at 60-65 for 24 hours. The benzene is removed by means of steam and the resulting monoazo dye of the formula is salted
EMI0001.0047
from the solution with potassium chloride made alkaline with soda, filter it off, wash and dry it.
The dye is a yellow powder. It dissolves in warm water and in concentrated sulfuric acid with a greenish yellow color. Wool is dyed from neutral to slightly acidic baths in clear, greenish yellow tones. The coloring is very lightfast, waterfast and seawaterfast.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH311042T | 1952-03-05 | ||
| CH304389T | 1952-03-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH311042A true CH311042A (en) | 1955-11-15 |
Family
ID=25734831
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH311042D CH311042A (en) | 1952-03-05 | 1952-03-05 | Process for the preparation of a yellow monoazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH311042A (en) |
-
1952
- 1952-03-05 CH CH311042D patent/CH311042A/en unknown
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