CH308758A - Process for the preparation of a disazo dye. - Google Patents
Process for the preparation of a disazo dye.Info
- Publication number
- CH308758A CH308758A CH308758DA CH308758A CH 308758 A CH308758 A CH 308758A CH 308758D A CH308758D A CH 308758DA CH 308758 A CH308758 A CH 308758A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- disazo dye
- blue
- dye
- preparation
- Prior art date
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- OXQJOAGKNHVOAI-UHFFFAOYSA-N 5-amino-6-methoxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=C(N)C(OC)=CC=C21 OXQJOAGKNHVOAI-UHFFFAOYSA-N 0.000 claims description 4
- LHEPTIRLRDQRQR-UHFFFAOYSA-N 2,4-bis(2-methylphenoxy)aniline Chemical compound CC1=CC=CC=C1OC1=CC=C(N)C(OC=2C(=CC=CC=2)C)=C1 LHEPTIRLRDQRQR-UHFFFAOYSA-N 0.000 claims description 3
- 108010010803 Gelatin Proteins 0.000 claims description 3
- 239000003086 colorant Substances 0.000 claims description 3
- 229920000159 gelatin Polymers 0.000 claims description 3
- 239000008273 gelatin Substances 0.000 claims description 3
- 235000019322 gelatine Nutrition 0.000 claims description 3
- 235000011852 gelatine desserts Nutrition 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 241000896693 Disa Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- -1 aminoazo Chemical group 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005406 washing Methods 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/08—Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 302911. Verfahren zur Herstellung eines Disazofarbstoffes. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines Disa.zofarb- stoffes. Das Verfahren ist dadurch gekenn zeichnet, dass man dianotiertes 1-Amino-2,4-di- (2'-methyl-phenoxy) -benzol mit 1-Amino-2- methoxy-naphthalin-6-sulfonsäure kuppelt,
den erhaltenen Monoazofarbstoff weiterdiazo- tiert und in alkalischem Medium mit 1-Ace- tyl - amino - 8 - oxynaphthalin- 3, 6-disulfonsäure vereinigt.
Der erhaltene neue Disazofarbstoff stellt ein dunkles Pulver dar, das sich in Wasser mit blaugrüner Farbe löst und Gelatineschich- ten in reinen, sehr gut fixierten, blaugrünen Tönen färbt.
<I>Beispiel:</I> 30,5 Teile 1-Amino-2,4-di-(2'-methyl-phen- oxy)-benzol werden vorteilhaft mit Alkohol oder einem andern geeigneten Lösungsmittel gelöst und bei 3-5 indirekt dianotiert. Durch Eiszugabe wird die Temperatur auf 0 ein gestellt und eine schwach lackmussaure Lö sung von 25,3 Teilen 1-Amino-2-methoxy- naphthalin-6-sulfonsäure zum Diazokörper zu laufen gelassen.
Die Kupplung wird bei schwach lackmussaurer Reaktion zu Ende ge führt und hierauf der gebildete Aminoazo- farbstoff vorteilhaft isoliert und nachgewa- sehen, bis im Filtrat keine 1-Amino-2-methoxy- naphthalin-6-sulfonsäure mehr nachweisbar ist. Das feuchte Filtriergut wird nun bei Raumtemperatur bei schwach brillantalkali scher Reaktion angeschlämmt, 7,5 Teile NaN02 zugegeben und hierauf bei 14 25 Teile konz. Salzsäure zugestürzt.
Es wird während meh reren Stunden bei 14-16 ausdiazotiert, ein Nitritüberschuss gegebenenfalls mit Sulfamin- säure zerstört und hierauf die Diazoverbin- dung auf 0-3 gekühlt. Sie wird dann in Gegenwart von Pyridin bei 0-5 mit einer sodaalkalischen oder aminoniakalischen Lö sung von 36,1 Teilen 1-Acetyl-amino-8-oxy- naphthalin-3,6-disulfonsäure vereinigt..
Nach beendigter Kupplung wird der Farbstoff mit Kochsalz ausgefällt und abfiltriert. Hierauf wird er durch gründliches Waschen oder Um lösen gereinigt und getrocknet. Er stellt ein dunkles Pulver dar, löst sich in Wasser mit blaugrüner Farbe und färbt Gelatineschichten in reiner blaugrüner Nuance.
Additional patent to main patent No. 302911. Process for the production of a disazo dye. The subject of the present patent is a process for the production of a disa.zo dye. The process is characterized in that dianotated 1-amino-2,4-di- (2'-methyl-phenoxy) -benzene is coupled with 1-amino-2-methoxy-naphthalene-6-sulfonic acid,
the monoazo dye obtained is further diazotized and combined with 1-acetyl-amino-8-oxynaphthalene-3,6-disulfonic acid in an alkaline medium.
The new disazo dye obtained is a dark powder which dissolves in water with a blue-green color and colors gelatin layers in pure, very well fixed, blue-green tones.
<I> Example: </I> 30.5 parts of 1-amino-2,4-di- (2'-methyl-phenoxy) -benzene are advantageously dissolved with alcohol or another suitable solvent and at 3-5 indirectly dianoted. The temperature is set to 0 by adding ice and a weakly lacquer acid solution of 25.3 parts of 1-amino-2-methoxynaphthalene-6-sulfonic acid is allowed to run to the diazo body.
The coupling is completed with a weak lacquer acid reaction and the aminoazo dye formed is then advantageously isolated and rewashed until 1-amino-2-methoxynaphthalene-6-sulfonic acid can no longer be detected in the filtrate. The moist filter material is then suspended at room temperature in a weakly brilliant alkali shear reaction, 7.5 parts of NaNO2 are added and then at 14 25 parts of conc. Hydrochloric acid fell.
It is diazotized for several hours at 14-16, an excess of nitrite is destroyed with sulfamic acid, if necessary, and the diazo compound is then cooled to 0-3. It is then combined in the presence of pyridine at 0-5 with a soda-alkaline or aminoniakalischen solution of 36.1 parts of 1-acetyl-amino-8-oxynaphthalene-3,6-disulfonic acid.
When the coupling is complete, the dye is precipitated with sodium chloride and filtered off. Then it is cleaned and dried by thorough washing or dissolving. It is a dark powder, dissolves in water with a blue-green color and colors gelatin layers in a pure blue-green shade.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH308758T | 1951-07-31 | ||
| CH302911T | 1954-11-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH308758A true CH308758A (en) | 1955-07-31 |
Family
ID=25734561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH308758D CH308758A (en) | 1951-07-31 | 1951-07-31 | Process for the preparation of a disazo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH308758A (en) |
-
1951
- 1951-07-31 CH CH308758D patent/CH308758A/en unknown
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