CH213567A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH213567A CH213567A CH213567DA CH213567A CH 213567 A CH213567 A CH 213567A CH 213567D A CH213567D A CH 213567DA CH 213567 A CH213567 A CH 213567A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- dye
- parts
- azo dye
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 239000000987 azo dye Substances 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 3
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 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 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling 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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 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
- C09B43/44—Preparation of azo dyes from other azo compounds by substituting amine groups for hydroxyl groups or hydroxyl groups for amine groups; Desacylation of amino-acyl groups; Deaminating
-
- 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
- C09B31/06—Disazo dyes from a coupling component "C" containing a directive hydroxyl group
- C09B31/068—Naphthols
- C09B31/072—Naphthols containing acid groups, e.g. —CO2H, —SO3H, —PO3H2, —OSO3H, —OPO2H2; Salts thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 205534. Verfahren zur Herstellung eines Azofarbstoffes. Nach dem durch das Hauptpatent ge schützten Verfahren erhält man einen für das Färben von Acetatseide besonders gut geeigneten Farbstoff, wenn man 4-Acyl- amino-l-amino-5-methogybenzol Jiazotiert und die Diazoverbindung mit 1-Amino-3- methyl-6-methogybenzol kuppelt und dann die Acylgruppe abspaltet.
Dieser Farbstoff lässt sich auf der Faser diazotieren und mit beispielsweise 2,3-Ogynaphthoes-äure kuppeln. Man erhält .so blaue bis schwarze Färbungen von sehr guter Echtheit.
Wie nun weiter gefunden wurde, erhält man einen Farbstoff mit den gleichen guten Eigenschaften, wenn man die aus 4-Acyl- amino-l-amino-5-methogybenzol hergestellte Diazoverbindung mit 1-Amino-3.6-dimethyl- benzol kuppelt und dann die Acylgruppe ab spaltet. Der so erhaltene Farbstoff schmilzt bei 165 .
<I>Beispiel;</I> <B>16,5</B> Teile 4 .- Acetamino -1- amino - 5 - methogybenzol werden in 500 Teilen Wasser und 25 Teilen Salzsäure 20' B6 gelöst und unter Abkühlung durch Zugabe einer Lö sung von 7 Teilen Natriumnitrit diazotiert.
Zu der Diazolösung gibt man eine Lösung von 12,1 Teilen 1-Amino-3. 6-dimethylbenzol in 200 Teilen Wasser und 10 Teilen Salz säure und .stumpft die Salzsäure durch allmähliches Zulaufenlassen einer Lösung von Natriumacetat ab. Es entsteht ein dicker Farbstoffbrei, der durch Verdünnen mit ,Wasser und Zugabe von Kochsalz rührfähig gehalten wird.
Nach beendeter Kupplung wird auf<B>50-60'</B> angewärmt und abge- presst.
Der Filterkuchen wird in 500 Teile Al kohol eingetragen, mit Natronlauge neutral gestellt, mit einer Lösung von 20 Teilen Natriumhydrogyd versetzt und etwa 2 Stun den unter Rückfluss gekocht, bis eine Probe nach Verdampfen des Alkohols und Ab filtrieren völlig salzsäurelöslich ist. Dann wird,der Alkohol abdestilliert, der Farbstoff mit Wasser aufgenommen, gepresst und mit Wasser neutral gewaschen. Das Produkt fällt in griställchen an, die bei 165 schmel zen.
Der Farbstoff färbt Acetyleellulose aus der Suspension gelb und gibt nach Diazotie- ren und Entwickeln mit 2,3-Oxynaphthoe- säure klare blaue, bei stärkerer Färbung schwarze Töne, welche neben den für diese Farbstoffklasse üblichen Echtheitseigen schaften sich durch eine besonders gute Abendfarbe und eine verbesserte Lichtecht heit gegenüber mit ähnlichen bekannten Farbstoffen erhaltene Färbungen auszeich net.
<B> Additional patent </B> to main patent no. 205534. Process for the production of an azo dye. According to the process protected by the main patent, a dye particularly suitable for dyeing acetate silk is obtained if 4-acylamino-1-amino-5-methogybenzene is jiazotized and the diazo compound with 1-amino-3-methyl-6 -methogybenzene couples and then splits off the acyl group.
This dye can be diazotized on the fiber and coupled with, for example, 2,3-ogynaphthoic acid. This gives blue to black dyeings of very good fastness.
As has now also been found, a dye with the same good properties is obtained if the diazo compound prepared from 4-acylamino-1-amino-5-methogybenzene is coupled with 1-amino-3,6-dimethylbenzene and then the acyl group splits off. The dye thus obtained melts at 165.
<I> Example; </I> <B> 16.5 </B> parts of 4 .- Acetamino -1-amino-5-methogybenzene are dissolved in 500 parts of water and 25 parts of hydrochloric acid 20 'B6 and, with cooling, by addition a solution of 7 parts of sodium nitrite diazotized.
A solution of 12.1 parts of 1-amino-3 is added to the diazo solution. 6-dimethylbenzene in 200 parts of water and 10 parts of hydrochloric acid and dulls the hydrochloric acid by gradually running in a solution of sodium acetate. The result is a thick paste of dyestuff, which is kept stirrable by diluting with water and adding sodium chloride.
After the coupling is complete, it is heated to <B> 50-60 '</B> and pressed.
The filter cake is introduced into 500 parts of alcohol, made neutral with sodium hydroxide solution, treated with a solution of 20 parts of sodium hydrogen and refluxed for about 2 hours until a sample is completely soluble in hydrochloric acid after the alcohol has evaporated and filtered off. Then, the alcohol is distilled off, the dye is taken up with water, pressed and washed neutral with water. The product is obtained in granules that melt at 165.
The dyestuff colors acetylellulose yellow from the suspension and, after diazotizing and developing with 2,3-oxynaphthoic acid, gives clear blue shades, with stronger coloration black shades which, in addition to the fastness properties customary for this class of dyestuff, are characterized by a particularly good evening color and a improved lightfastness compared with dyeings obtained with similar known dyes.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH205534T | 1939-06-22 | ||
| CH213567T | 1939-06-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH213567A true CH213567A (en) | 1941-02-15 |
Family
ID=25724191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH213567D CH213567A (en) | 1939-06-22 | 1939-06-22 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH213567A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2570946A1 (en) * | 1984-10-01 | 1986-04-04 | Oreal | NOVEL KERATIN FIBER DYEING COMPOSITIONS CONTAINING AZOIC DYE, PROCESS FOR PREPARING THE DYE AND IMPLEMENTING SAID COMPOSITIONS FOR DYING KERATIN FIBERS |
-
1939
- 1939-06-22 CH CH213567D patent/CH213567A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2570946A1 (en) * | 1984-10-01 | 1986-04-04 | Oreal | NOVEL KERATIN FIBER DYEING COMPOSITIONS CONTAINING AZOIC DYE, PROCESS FOR PREPARING THE DYE AND IMPLEMENTING SAID COMPOSITIONS FOR DYING KERATIN FIBERS |
| US4886517A (en) * | 1984-10-01 | 1989-12-12 | L'oreal | Dyeing composition for human hair containing an azo dye |
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