CH224352A - Process for the preparation of a chromium-containing azo dye. - Google Patents
Process for the preparation of a chromium-containing azo dye.Info
- Publication number
- CH224352A CH224352A CH224352DA CH224352A CH 224352 A CH224352 A CH 224352A CH 224352D A CH224352D A CH 224352DA CH 224352 A CH224352 A CH 224352A
- Authority
- CH
- Switzerland
- Prior art keywords
- chromium
- azo dye
- dye
- containing azo
- preparation
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 10
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims description 9
- 229910052804 chromium Inorganic materials 0.000 title claims description 9
- 239000011651 chromium Substances 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- -1 p-tert-butylphenyl Chemical group 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- NNZXDXMEXBYSRF-UHFFFAOYSA-N 2-methyl-4h-pyrazol-3-one Chemical compound CN1N=CCC1=O NNZXDXMEXBYSRF-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 229920002678 cellulose Polymers 0.000 description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 229920003086 cellulose ether Polymers 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RBODBGADQNATTQ-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-5-methyl-4h-pyrazol-3-one Chemical compound O=C1CC(C)=NN1C1=CC=C(C(C)(C)C)C=C1 RBODBGADQNATTQ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920002955 Art silk Polymers 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/16—Monoazo compounds containing chromium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines ehromhaltigen Azofarbstoffes. Gegenstand des Hauptpatentes ist ein Verfahren zur Herstellung eines chromhalti- gen Azofarbstoffes, bei ,dem man den durch Kuppeln von diazotiertem 1-Amino-2-ogy-5- nitrobenzol mit 2-Ogybutylnaphthalin erhält lichen Azofarbstoff mit chromabgebenden Mitteln behandelt.
Es wurde nun gefunden, dass man eben falls einen chromhaltigen Azofarbstoff er hält, wenn man den durch Kuppeln von di- azotiertem 1- Amino-2-ogy-5-nitrobenzol mit 1-(p-tert.-Butylphenyl)-3-methyl-5-pyrazolon erhältlichen Azofarbstoff mit chromabgeben den Mitteln behandelt.
Die Überführung des metallfreien Farb stoffes in den chromhaltigen Azofarbstoff gelingt leicht nach den üblichen Verfahren durch Erhitzen mit chromabgebenden Mit teln, beispielsweise den Salzen des Chroms. Man kann dabei in wässriger saurer, neutraler oder alkalischer Lösung oder auch in orga nischen Lösungsmitteln, z. B. Alkoholen, Aminen, Carbonsäureamidschmelzen oder ge- schmolzenen Ammoniumsalzen von Carbon- säuren, gegebenenfalls auch unter erhöhtem Druck, arbeiten.
Der neue Farbstoff zeichnet sich .dadurch aus, dass er bei sehr guter Lichtechtheit und grosser Ausgiebigkeit vorzüglich in organi schen, plastischen Massen mit oranger Farbe löslich ist. Er eignet sich .daher. hervorragend zum Färben von Gebüden, z. B. Überzügen, Filmen, Folien, Fäden, Bändern oder Form stücken aus Celluloseestern und -äthern, Poly- vinylverbindungen, Superpolyamiden und an dern natürlichen oder künstlichen Harzen.
Auch in den bei der Verarbeitung von Cellu- loseestern und -äth-ern gebräuchlichen Lö sungsmitteln, z. B. in Butylacetat, löst sich der neue Farbstoff ausgezeichnet, so daB er beispielsweise zum Färben von Lacken oder Spinnlösungen für die Herstellung von Ace- tatkunstseide verwendet werden kann.
Die in dem nachstehenden Beispiel ange gebenen Teile sind Gewichtsteile. Beispiel: 39,5 Teile des Azofarbstoffes aus diazo- tiertem 1- Amino - 2 - ogy- 5 - nitrobenzol und 1-(p-tert.-Butylphenyl)-3-methyl-5-pyrazolon suspendiert man in 300 Teilen Formamid und einer wässrigen Lösung von 31,7 Teilen einer 24%i,
-en Chromogydpaste und 10 Teilen 100%iger Ameisensäure in 30 Teilen Wasser und erhitzt 3 Stunden lang auf<B>110'.</B> Das Gemisch wird mit Wasser verdünnt, der Farbstoff abgesaugt und getrocknet. Da der rohe Farbstoff Ammoniak gebunden ent hält, wird er durch Kochen mit Alkalilauge von diesem befreit und dann durch Ansäuern in die Farbsäure übergeführt.
Dank seiner guten Löslichkeit in den verschiedenen Cellu- loseesterlacken kann man mit dem Farbstoff kräftige, lichtechte orange Färbungen er, zielen.
Process for the preparation of an azo dye containing Ehrom. The subject of the main patent is a process for the production of a chromium-containing azo dye, in which the azo dye obtained by coupling diazotized 1-amino-2-ogy-5-nitrobenzene with 2-ogybutylnaphthalene is treated with chromium-releasing agents.
It has now been found that if a chromium-containing azo dye is obtained, if one uses 1- (p-tert-butylphenyl) -3-methyl by coupling the azotized 1-amino-2-ogy-5-nitrobenzene with -5-pyrazolon available azo dye treated with chromium donating agents.
The conversion of the metal-free dye into the chromium-containing azo dye is easily achieved by the usual methods by heating with chromium-releasing agents, for example the salts of chromium. You can in aqueous acidic, neutral or alkaline solution or in organic solvents such. B. alcohols, amines, carboxamide melts or molten ammonium salts of carboxylic acids, possibly also under increased pressure, work.
The new dye is characterized by the fact that it is extremely soluble in organic, plastic masses with an orange color, with very good lightfastness and great abundance. It is therefore suitable. excellent for coloring buildings, e.g. B. coatings, films, foils, threads, tapes or moldings made of cellulose esters and ethers, polyvinyl compounds, super polyamides and other natural or synthetic resins.
Also in the solvents commonly used in the processing of cellulose esters and ethers, e.g. B. in butyl acetate, the new dye dissolves excellently, so that it can be used, for example, for dyeing lacquers or spinning solutions for the production of acetate artificial silk.
The parts given in the example below are parts by weight. Example: 39.5 parts of the azo dye from diazo- tated 1-amino-2-ogy-5-nitrobenzene and 1- (p-tert-butylphenyl) -3-methyl-5-pyrazolone are suspended in 300 parts of formamide and one aqueous solution of 31.7 parts of a 24% i,
-en Chromogyd paste and 10 parts of 100% formic acid in 30 parts of water and heated to <B> 110 'for 3 hours. </B> The mixture is diluted with water, the dye is suctioned off and dried. Since the raw dye contains bound ammonia, it is freed from this by boiling with alkali and then converted into the dye acid by acidification.
Thanks to its good solubility in the various cellulose ester lacquers, the dye can be used to achieve strong, lightfast orange colorations.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE224352X | 1940-07-06 | ||
| CH221017T | 1941-05-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH224352A true CH224352A (en) | 1942-11-15 |
Family
ID=25726517
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH224352D CH224352A (en) | 1940-07-06 | 1941-05-16 | Process for the preparation of a chromium-containing azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH224352A (en) |
-
1941
- 1941-05-16 CH CH224352D patent/CH224352A/en unknown
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