CH166076A - Process for the production of a new azo dye. - Google Patents
Process for the production of a new azo dye.Info
- Publication number
- CH166076A CH166076A CH166076DA CH166076A CH 166076 A CH166076 A CH 166076A CH 166076D A CH166076D A CH 166076DA CH 166076 A CH166076 A CH 166076A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- production
- azo dye
- dimethyl
- new azo
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 4
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- -1 wool Polymers 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- OCISOSJGBCQHHN-UHFFFAOYSA-N 3-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC(O)=CC2=C1 OCISOSJGBCQHHN-UHFFFAOYSA-N 0.000 claims 1
- 229920000297 Rayon Polymers 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000002964 rayon Substances 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- SCCCFNJTCDSLCY-UHFFFAOYSA-N 1-iodo-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(I)C=C1 SCCCFNJTCDSLCY-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- BFSPAPKTIGPYOV-BQYQJAHWSA-N (e)-1-[4-(4-hydroxyphenyl)piperazin-1-yl]-3-thiophen-2-ylprop-2-en-1-one Chemical group C1=CC(O)=CC=C1N1CCN(C(=O)\C=C\C=2SC=CC=2)CC1 BFSPAPKTIGPYOV-BQYQJAHWSA-N 0.000 description 1
- 229920002955 Art silk Polymers 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 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)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines neuen Azofarbstoffes. Es wurde gefunden, dass man einen neuen Azofarbstoff der Formel
EMI0001.0005
erhält, wenn man das 2'. 4'-Dimethyl-4-di- azotriphenylamin mit dem 4-Chlor-2-toluidid der 2. 3-OYynaphthoesäure kuppelt.
Der so erhaltene Farbstoff bildet ein blaues Pulver. Auf geeigneten Substraten, wie zum Beispiel Baumwolle, Wolle, Kunst seide, hergestellt, färbt er diese in reinen. sehr echten blauen Tönen.
<I>Beispiel:</I> 28,8 Teile<B>29'.</B> 4'-Dimethyl-4-a,minotriphc- rivlamin werden wie üblich diazotiert und in eine Lösung von 31,1 Teilen des 4-Chlor-2- toluidids der 2. 3-Ogynaphthoesäure, 60 Tei len 30 ö iger Natriumhydrogydlösung, 15 Teilen Soda und 2000 Teilen Wasser ein getragen. Der gebildete Farbstoff fällt sofort aus. Er wird filtriert, gewaschen und ge trocknet.
Das 2' . 4'-Dimethyl - 4 - aminotriphenyl- amin kann wie folgt dargestellt werden: 120,.5 Teile 2'. 4'-Dimethyldiphenylamin- 2-carbonsäure, F. 186 , 187,5 Teile p-Nitro- jodbenzol, 80 Teile Kaliumkarbonat, 375 Teile Nitrobenzol und 5 Teile Naturkupfer C werden während einer Stunde bei 195 bis 200 im Ölbad erwärmt. Das Nitrobenzol und das überschüssige p-Nitrojodbenzol wer den mit Wasserdampf abgetrieben.
Es bleibt eine braunrote Lösung, aus der man mit Salz säure die 2" . 4"-Dimethyl-4'-nitrotriphenyl- amin-2-carbonsättre als gelber Niederschlag abscheidet, zurück. Durch Kristallisation aus Eisessig erhält man den Körper in gelben Blättchen vom F. 197 bis 198 . 100 Teile 2" . 4"-Dimethyl-4'-nitrotriphe- nylamin-2-carbonsäure, 250 Teile Nitroben- zol und 5 Teile Naturkupfer C werden wäh rend 4 bis 5 Stunden unter Rückfluss erhitzt.
Das Nitrobenzol wird mit Wasserdampf ab getrieben. Es bleibt ein in der Kälte er starrendes 01 zurück. Durch Kristallisation aus Alkohol erhält man das 2'. 4'-Dimethyl- 4-nitrotriphenylamin in orangegelben Blätt chen vom F. 101 bis 102'. Durch Reduktion mit Eisen und Salzsäure in Alkohol erhält man das 2' . 4'-Dimethyl-4-aminotriphenyl- amin als farblosen Körper, dessen Acetyl- derivat bei 180 bis 1.81 schmilzt.
Process for the production of a new azo dye. It has been found that a new azo dye of the formula
EMI0001.0005
if you get the 2 '. 4'-Dimethyl-4-diazotriphenylamine couples with the 4-chloro-2-toluidide of the 2. 3-OYynaphthoic acid.
The dye thus obtained forms a blue powder. Produced on suitable substrates such as cotton, wool, artificial silk, he dyes them in pure. very real blue tones.
<I> Example: </I> 28.8 parts <B> 29 '. </B> 4'-Dimethyl-4-a, minotriphcrivlamin are diazotized as usual and poured into a solution of 31.1 parts of the 4th -Chlor-2-toluidids of 2. 3-ogynaphthoic acid, 60 parts of 30 iger sodium hydrogen solution, 15 parts of soda and 2000 parts of water. The dye formed precipitates immediately. It is filtered, washed and dried.
The 2 '. 4'-Dimethyl - 4 - aminotriphenylamine can be represented as follows: 120.5 parts of 2 '. 4'-Dimethyldiphenylamine-2-carboxylic acid, mp 186, 187.5 parts of p-nitroiodobenzene, 80 parts of potassium carbonate, 375 parts of nitrobenzene and 5 parts of natural copper C are heated for one hour at 195 to 200 in an oil bath. The nitrobenzene and the excess p-nitroiodobenzene who are driven off with steam.
A brown-red solution remains, from which the 2 ". 4" -Dimethyl-4'-nitrotriphenylamine-2-carboxylic acid is deposited as a yellow precipitate with hydrochloric acid. Crystallization from glacial acetic acid gives the body in yellow leaves with a melting point of 197 to 198. 100 parts of 2 ". 4" -Dimethyl-4'-nitrotriphenylamine-2-carboxylic acid, 250 parts of nitrobenzene and 5 parts of natural copper C are refluxed for 4 to 5 hours.
The nitrobenzene is driven off with steam. There remains an 01 staring in the cold. The 2 'is obtained by crystallization from alcohol. 4'-Dimethyl-4-nitrotriphenylamine in orange-yellow leaves from 101 to 102 '. The 2 'is obtained by reduction with iron and hydrochloric acid in alcohol. 4'-Dimethyl-4-aminotriphenylamine as a colorless body, the acetyl derivative of which melts at 180 to 1.81.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH166076T | 1932-07-13 | ||
| CH163540T | 1932-07-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH166076A true CH166076A (en) | 1933-12-15 |
Family
ID=25717793
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH166076D CH166076A (en) | 1932-07-13 | 1932-07-13 | Process for the production of a new azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH166076A (en) |
-
1932
- 1932-07-13 CH CH166076D patent/CH166076A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH166076A (en) | Process for the production of a new azo dye. | |
| CH166075A (en) | Process for the production of a new azo dye. | |
| CH166077A (en) | Process for the production of a new azo dye. | |
| CH166078A (en) | Process for the production of a new azo dye. | |
| CH167047A (en) | Process for the production of a metal-containing dye. | |
| CH166074A (en) | Process for the production of a new azo dye. | |
| CH169244A (en) | Process for the production of a new azo dye. | |
| CH167051A (en) | Process for the production of a metal-containing dye. | |
| CH131258A (en) | Process for the production of a new azo dye. | |
| CH162149A (en) | Process for the production of a new azo dye. | |
| CH167173A (en) | Process for the production of a new azo dye. | |
| CH177839A (en) | Process for the production of a new azo dye. | |
| CH164429A (en) | Process for the production of a new azo dye. | |
| CH166073A (en) | Process for the production of a new azo dye. | |
| CH131253A (en) | Process for the production of a new azo dye. | |
| CH131259A (en) | Process for the production of a new azo dye. | |
| CH169245A (en) | Process for the production of a new azo dye. | |
| CH175031A (en) | Process for the production of a new azo dye. | |
| CH167040A (en) | Process for the production of a metal-containing dye. | |
| CH222138A (en) | Process for the production of a new chromium-containing azo dye. | |
| CH220748A (en) | Process for the preparation of a new pyrazolone derivative. | |
| CH131254A (en) | Process for the production of a new azo dye. | |
| CH237130A (en) | Process for the production of a new azo dye. | |
| CH164431A (en) | Process for the production of a new azo dye. | |
| CH163540A (en) | Process for the production of a new azo dye. |