CH272489A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH272489A CH272489A CH272489DA CH272489A CH 272489 A CH272489 A CH 272489A CH 272489D A CH272489D A CH 272489DA CH 272489 A CH272489 A CH 272489A
- Authority
- CH
- Switzerland
- Prior art keywords
- azo dye
- preparation
- red
- parts
- dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 239000000975 dye Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 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
- 150000001989 diazonium salts Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002268 wool Anatomy 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
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/28—Amino naphthols
- C09B29/30—Amino naphtholsulfonic acid
-
- 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
- C09B29/16—Naphthol-sulfonic acids
-
- 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
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
- C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
- C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Azofarbstoffes. Es wurde gefunden, dass man zu einem wertvollen Azofarbstoff gelangt, wenn man dianotierten 4'-Tertiäranivl-4-aminodiphenvl- äther mit. 1-OYynaplitlialin-3,6-disulfonsäure vereinigt.
Der neue Farbstoff bildet ein rotes Pulver, (las sich in Wasser mit roter Farbe löst und Wolle aus essigsaurem Bade rein rot färbt.
Der beim vorliegenden Verfahren als Aus gangsstoff dienende 4'-Tertiäramyl-4-aniino- diphenyläther kann nach an sieh bekannter .Methode durch Kondensation von 4-Tertiär- aiiwl-l-oay#henzol mit 1-Clilor-4-nitrobenzol und nachfolgende Reduktion der Nitrogruppe des erhaltenen 4'-Tertiäramyl-4-nitrodiphenyl- äthers zur Aininogruppe hergestellt werden.
Die Dianotierung kann wie üblieli, z. B. mit Salzsäure und Natriumnitrit, durchgeführt werden.
Die Kupplung erfolgt mit Vorteil in alka lischem, vorzugsweise alkaliearbonatalkali- sehem Mediiini.
<I>Beispiel:</I> 13 Teile 4'-Tert.iäramyl-4-aminodiphenyl- äther werden finit 19 Teilen konzentrierter Salzsäure verrieben und mit Eis versetzt. Die weisse Chlorhydratsuspension wird bei 00 mit. einer konzentrierten Lösung von 3,5 Teilen Na triumnitrit in Wasser vermischt. Man erhält eine klare Diazoniumlösung.
Der Lösung von 18 Teilen des Dinatriuni- salzes der 1-Oxynaplithalin-3,6-disulfonsäure in 350 Teilen Wasser werden noch 15 Teile wasserfreies Natriumearbona.t zugesetzt. Obige Diazoniumlösung wird bei 0 langsam einge tragen. Wenn in der braunroten Farbstoff suspension keine Diazoniumverbindung mehr nachgewiesen werden kann, wird der Farb stoff abgesaugt, mit verdünnter Na.trium- ehloridlösüng gewaschen und getrocknet.
Process for the preparation of an azo dye. It has been found that a valuable azo dye is obtained if one with dianotated 4'-Tertiäranivl-4-aminodiphenvl- ether. 1-OYynaplitlialin-3,6-disulfonic acid combined.
The new dye forms a red powder, (can be dissolved in water with a red color, and wool from acetic acid bath dyes pure red.
The 4'-tertiaryamyl-4-aniino-diphenyl ether used as the starting material in the present process can, according to a known method, by condensation of 4-tertiary aiiwl-l-oay # henzene with 1-chloro-4-nitrobenzene and subsequent reduction the nitro group of the 4'-tertiaryamyl-4-nitrodiphenyl ether obtained to the amino group.
The Dianotierung can as usual, z. B. with hydrochloric acid and sodium nitrite.
The coupling is advantageously carried out in alkaline, preferably alkali carbonate alkaline media.
<I> Example: </I> 13 parts of 4'-tert.iäramyl-4-aminodiphenyl ether are finely triturated with 19 parts of concentrated hydrochloric acid and mixed with ice. The white hydrochloride suspension is at 00 with. a concentrated solution of 3.5 parts of sodium nitrite mixed in water. A clear diazonium solution is obtained.
A further 15 parts of anhydrous sodium carbonate are added to the solution of 18 parts of the dinatrium salt of 1-oxynaplithalin-3,6-disulfonic acid in 350 parts of water. The above diazonium solution is slowly entered at 0. If no more diazonium compounds can be detected in the brown-red dye suspension, the dye is suctioned off, washed with dilute sodium chloride solution and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH272489T | 1947-04-30 | ||
| CH270538T | 1948-02-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH272489A true CH272489A (en) | 1950-12-15 |
Family
ID=25731200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH272489D CH272489A (en) | 1947-04-30 | 1947-04-30 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH272489A (en) |
-
1947
- 1947-04-30 CH CH272489D patent/CH272489A/en unknown
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