CH185836A - Process for the production of a new azo dye. - Google Patents
Process for the production of a new azo dye.Info
- Publication number
- CH185836A CH185836A CH185836DA CH185836A CH 185836 A CH185836 A CH 185836A CH 185836D A CH185836D A CH 185836DA CH 185836 A CH185836 A CH 185836A
- Authority
- CH
- Switzerland
- Prior art keywords
- azo dye
- production
- new azo
- new
- aminobenzene
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 3
- 229920002678 cellulose Polymers 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- -1 phenoxyacetylamino - 2 - ethoxy Chemical group 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- AOPRXJXHLWYPQR-UHFFFAOYSA-N 2-phenoxyacetamide Chemical compound NC(=O)COC1=CC=CC=C1 AOPRXJXHLWYPQR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- WEUHWXAXTHNSOG-UHFFFAOYSA-N 2,5-dichloro-5-nitrocyclohexa-1,3-diene Chemical compound ClC1(CC=C(C=C1)Cl)[N+](=O)[O-] WEUHWXAXTHNSOG-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000000047 product Substances 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
<B>Zusatzpatent</B> zum Hauptpatent Nr. 182961. Verfahren zur Herstellung eines neuen Azofarbstoffes. Es wurde gefunden, dass man ehren neuen Azofarbstoff erhält, wenn man dianotiertes 4 -(4'-Methyl-) phenoxyacetylamirro - 2 - äthoxy- 5-R-methoxyäthyläther-1-aminobenzol mit 2,3- Oxynaplrthoesäure-1'-naphthylamid .vereinigt. Der neue Farbstoff bildet ein blaues, in Wasser unlösliches Pulver. Auf geeigneten Substraten, wie zum Beispiel Zellulose, her gestellt, färbt es diese in wertvollen, blauen Tönen.
<I>Beispiel:</I> 37,4 Teile 4-(4'-Methyl-)phenoxyacetyl- ami no - 2 - äthoxy - 5 - (3- methoxyäthyl äther -1- aminobenzol werden wie üblich dianotiert und in eine Lösung von 31,3 Teilen 2,3-Oxy- naphthoesäure-1'-naphthylamid, 60 Teilen 30 /oiger Natronlauge, 30 Teilen Soda und 2000 Teilen Wasser eingetragen. Der ge bildete Farbstoff fällt sofort aus. Der blaue Niederschlag wird filtriert und getrocknet.
Das 4-(4'-Methyl-)phenoxyacetylamino-2- äthozy-5-p-rnethoxyäthyläther-1-anrirrobenzol kann hergestellt werden durch Umsetzen von 2,5-Dichlor-o-nitrobenzol mit Glykolmono- methyläther zum 4-Chlor-2-nitrobenzol-l-ss- methoxyäthyläther. Dieses wird dann zum 4-Chlor-2-aminobenzol-l-p-meth oxyätbyläther reduziert, welcher acetyliert,
nitriert und durch Abspalten der Acetylgruppe in den 5-Nitro-4-chlor#-2-aminobenzol-l-p-metboxy- äthyläther übergeführt wird. Dieses Produkt wird nun mit Äthylalkohol umgesetzt, wo bei das 4-ständige Chloratom durch die Gruppe 002H5 ersetzt wird und hierauf durch Kondensation mit 4-(Methyl-)phenoxy- essigsäure und Reduzieren in das 4-(4'-Me- thyl-)
phenoxyacetylamin o-2-äth oxy-5- ss-m eth- oxyäthyläther-l-aminobenzol umgewandelt wird.
<B> Additional patent </B> to main patent No. 182961. Process for the production of a new azo dye. It has been found that a new azo dye is obtained if dianotated 4 - (4'-methyl-) phenoxyacetylamirro-2-ethoxy-5-R-methoxyethyl ether-1-aminobenzene is used with 2,3-oxynaplrthoic acid-1'-naphthylamide. united. The new dye forms a blue, water-insoluble powder. Produced on suitable substrates such as cellulose, it colors them in valuable blue tones.
<I> Example: </I> 37.4 parts of 4- (4'-methyl-) phenoxyacetylamine - 2 - ethoxy - 5 - (3-methoxyethyl ether -1- aminobenzene are dianotized as usual and put into a solution of 31.3 parts of 2,3-oxynaphthoic acid-1'-naphthylamide, 60 parts of 30% sodium hydroxide solution, 30 parts of soda and 2000 parts of water are introduced, the dyestuff formed precipitates out immediately. The blue precipitate is filtered and dried.
The 4- (4'-methyl-) phenoxyacetylamino-2-ethoxy-5-p-methoxyethyl ether-1-anirrobenzene can be prepared by reacting 2,5-dichloro-o-nitrobenzene with glycol monomethyl ether to give 4-chloro-2 -nitrobenzene-l-ss- methoxyethyl ether. This is then reduced to 4-chloro-2-aminobenzene-l-p-methoxyethyl ether, which acetylates
nitrated and converted by splitting off the acetyl group in the 5-nitro-4-chloro # -2-aminobenzene-l-p-metboxy-ethyl ether. This product is then reacted with ethyl alcohol, where the 4-position chlorine atom is replaced by the group 002H5 and then by condensation with 4- (methyl-) phenoxyacetic acid and reduction to the 4- (4'-methyl)
phenoxyacetylamine o-2-ethoxy-5- ss-m ethoxyethylether-l-aminobenzene is converted.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH182961T | 1936-02-11 | ||
| CH185836T | 1936-02-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH185836A true CH185836A (en) | 1936-08-15 |
Family
ID=25720811
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH185836D CH185836A (en) | 1936-02-11 | 1936-02-11 | Process for the production of a new azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH185836A (en) |
-
1936
- 1936-02-11 CH CH185836D patent/CH185836A/en unknown
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