CH251802A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH251802A CH251802A CH251802DA CH251802A CH 251802 A CH251802 A CH 251802A CH 251802D A CH251802D A CH 251802DA CH 251802 A CH251802 A CH 251802A
- Authority
- CH
- Switzerland
- Prior art keywords
- dicarboxylic acid
- parts
- anthradithiazole
- production
- vat dye
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 239000000984 vat dye Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 6
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 3
- 229920003043 Cellulose fiber Polymers 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 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
- 238000001035 drying Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZYHBRBAMLZPYSX-UHFFFAOYSA-N ClC1=C(C=CC=2C(C3=C(C(=CC=C3C(C12)=O)C(=O)O)Cl)=O)C(=O)O Chemical compound ClC1=C(C=CC=2C(C3=C(C(=CC=C3C(C12)=O)C(=O)O)Cl)=O)C(=O)O ZYHBRBAMLZPYSX-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- GFONXNPMXQPEMK-UHFFFAOYSA-N [O-]C(C1=C(C=CC2=C3N[S+](C(O)=O)S2)C3=CC2=CC=CC=C12)=O Chemical compound [O-]C(C1=C(C=CC2=C3N[S+](C(O)=O)S2)C3=CC2=CC=CC=C12)=O GFONXNPMXQPEMK-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
- C09B5/04—Pyrazolanthrones
-
- 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
- C09B5/10—Isothiazolanthrones; Isoxazolanthrones; Isoselenazolanthrones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Description
Verfahren zur Herstellung eines Küpenfarbatoffes. Es wurde gefunden, dass ein Küpenfarb- stoff hergestellt werden kann, wenn man 1 Mol 1, 9, 5,10-Anthr adithiazol-2, 6-dicarbon- säure oder eines ihrer funktionellen Deri vate mit 2 1Vlol 2-Aminoanthrachinon um setzt.
Der neue Farbstoff ist ein gelbes Pulver, das sich in konzentrierter Schwefelsäure mit roter Farbe löst und Cellulosefasern aus orangebrauner Küpe in farbstarken grünlich gelben Tönen färbt.
Für die Umsetzung mit 2-Aminoanthra- chinon kann die genannte 1,9,5,10-Anthra- clitliiazol - 2,6 - dicarbonsäure bezw. zweck mässig eines ihrer reaktionsfähigen, funk tionellen Derivate, z. B. das Säurechlorid, verwendet werden. Die Umsetzung kann bei spielsweise in einem indifferenten Lösungs mittel, zweckmässig von hohem Siedepunkt, vorgenommen werden.
Die als Ausgangsstoff benötigte 1,9,5,10 Anthradithiazol-2,6-dicarbonsäure der Formel
EMI0001.0027
kann wie folgt hergestellt werden: 18,25 Teile 1,5-Dichloranthrachinon-2,6- dicarbonsäure, 16,5 Teile Schwefel, 110 Teile kristallisiertes Natriumsulfid und 290 Teile 12 % iges Ammoniak werden im Rührauto- klaven während 8 Stunden auf 95-105 er hitzt.
Nach dem Erkalten saugt man den Autoklaveninhalt ab, löst den Filterrück- stancl in 600 Teilen siedendem Wasser auf, filtriert und salzt aus dem Filtrat das Di- natriumsalz der 1,9,5,10-Anthradithiazol- 2,6-dicarbonsäure mit Kochsalz aus.
Nun saugt man ab, wäscht mit gesättigter Koch salzlösung aus, kocht den Filterkuchen unter Zugabe von etwas Tierkohle mit Wasser auf, filtriert und fällt aus dem Fil trat die 1,9,5,10-Anthradithiazol-2,6-dicar- bonsäure mit Salzsäure aus. Nach dem Fil trieren, Waschen und Trocknen erhält man in guter Ausbeute ein gelbgrünes, kristallines Pulver, das unterhalb 450 nicht schmilzt.
Zur Herstellung des Säurechlorids wer den 11,8 Teile 1,9,5,10 - Anthradithiazol- 2,6-dicarbonsäure mit 12 Teilen Thionyl- chlorid und 530 Teilen trockenem o-Di- chlorbenzol während 1 Stunde zum Sieden erhitzt. Nach dem Abdestillieren von 65 Teilen des Gemisches - wobei das unver brauchte Thionylchlorid mit übergeht wird heiss abgesaugt und das Filtrat erkal ten gelassen. Das 1,9,5,
10-Anthradithiazol- 2,6-dicarbonsäure-chlorid kristallisiert in grünlichgelben Blättchen aus, die nach dem Filtrieren, Waschen und Trocknen bei 323 bis 325 schmelzen.
<I>Beispiel:</I> 13 Teile 1,9,5,10-Anthradithiazol-2,6-di- carbonsäure-chlorid und 800 Teile trockenes o-Dichlorbenzol werden unter Rühren auf 150-160 erhitzt und bei dieser Temperatur mit einer heissen Lösung von 14,9 Teilen 2-Aminoanthrachinon in 400 Teilen o-Di- chlorbenzol und 10 Teilen Pyridin versetzt. Nach 2stündigem Rühren bei Siedetempera tur ist die Farbstoffbildung beendet.
Man saugt den ausgefallenen Farbstoff in der Wärme ab, wäscht mit o-Dichlorbenzol und Alkohol aus und trocknet.
Process for the production of a vat dye. It has been found that a vat dye can be produced if 1 mol 1, 9, 5,10-anthreadithiazole-2, 6-dicarboxylic acid or one of its functional derivatives is reacted with 2 1 vol 2-aminoanthraquinone.
The new dye is a yellow powder that dissolves in concentrated sulfuric acid with a red color and dyes cellulose fibers from an orange-brown vat in strong greenish-yellow tones.
For the reaction with 2-aminoanthraquinone said 1,9,5,10-anthraclitliiazole - 2,6 - dicarboxylic acid or. expediently one of their reactive, func tional derivatives, eg. B. the acid chloride can be used. The reaction can be carried out, for example, in an inert solvent, advantageously with a high boiling point.
The 1,9,5,10 anthradithiazole-2,6-dicarboxylic acid of the formula required as starting material
EMI0001.0027
can be prepared as follows: 18.25 parts of 1,5-dichloroanthraquinone-2,6-dicarboxylic acid, 16.5 parts of sulfur, 110 parts of crystallized sodium sulfide and 290 parts of 12% ammonia are heated to 95% in a stirred autoclave for 8 hours. 105 he's hot.
After cooling, the contents of the autoclave are filtered off with suction, the filter residue is dissolved in 600 parts of boiling water, filtered and the disodium salt of 1,9,5,10-anthradithiazole-2,6-dicarboxylic acid is salted from the filtrate with common salt .
It is then filtered off with suction, washed with saturated sodium chloride solution, the filter cake is boiled with water with the addition of a little animal charcoal, filtered and the 1,9,5,10-anthradithiazole-2,6-dicarboxylic acid also falls out of the fil Hydrochloric acid. After filtering, washing and drying, a yellow-green, crystalline powder that does not melt below 450 is obtained in good yield.
To prepare the acid chloride, 11.8 parts of 1,9,5,10-anthradithiazole-2,6-dicarboxylic acid with 12 parts of thionyl chloride and 530 parts of dry o-dichlorobenzene are heated to the boil for 1 hour. After 65 parts of the mixture have been distilled off, the unused thionyl chloride also passes over, is suctioned off while hot and the filtrate is allowed to cool. The 1,9,5,
10-Anthradithiazole-2,6-dicarboxylic acid chloride crystallizes out in greenish-yellow flakes, which, after filtering, washing and drying, melt at 323 to 325.
<I> Example: </I> 13 parts of 1,9,5,10-anthradithiazole-2,6-dicarboxylic acid chloride and 800 parts of dry o-dichlorobenzene are heated to 150-160 with stirring and at this temperature a hot solution of 14.9 parts of 2-aminoanthraquinone in 400 parts of o-dichlorobenzene and 10 parts of pyridine are added. After stirring for 2 hours at the boiling temperature, the dye formation has ended.
The dyestuff which has precipitated out is suctioned off in the heat, washed with o-dichlorobenzene and alcohol and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH244838T | 1942-01-08 | ||
| CH251802T | 1942-01-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH251802A true CH251802A (en) | 1947-11-15 |
Family
ID=25728988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH251802D CH251802A (en) | 1942-01-08 | 1942-01-08 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH251802A (en) |
-
1942
- 1942-01-08 CH CH251802D patent/CH251802A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1026456B (en) | Process for the production of Kuepen dyes | |
| DE730336C (en) | Process for the production of dyes | |
| CH251802A (en) | Process for the production of a vat dye. | |
| CH251800A (en) | Process for the production of a vat dye. | |
| CH249556A (en) | Process for the production of a vat dye. | |
| CH244838A (en) | Process for the production of a vat dye. | |
| CH251801A (en) | Process for the production of a vat dye. | |
| CH251803A (en) | Process for the production of a vat dye. | |
| CH251805A (en) | Process for the production of a vat dye. | |
| DE469654C (en) | Process for the preparation of urea derivatives | |
| CH251804A (en) | Process for the production of a vat dye. | |
| DE878687C (en) | Process for the preparation of phthalocyanine dyes | |
| DE964977C (en) | Process for the production of cobalt-containing dyes of the o, o'-dioxyazomethine series | |
| CH243843A (en) | Process for the production of a vat dye. | |
| DE2429673A1 (en) | METHOD FOR PREPARING SYMMETRIC 4-HALOGEN-4 ', 4 "DIARYLAMINO-TRIPHENYLMETHANE COMPOUNDS | |
| DE734240C (en) | Process for the production of chromable dyes of the phthalein series | |
| DE651751C (en) | Process for the production of Kuepen dyes of the anthraquinone oxazole series | |
| CH97360A (en) | Process for the preparation of a condensation product of the anthraquinone series which can be used as dye and dye intermediate. | |
| DE1085994B (en) | Process for the production of dyes | |
| CH247604A (en) | Process for the production of a vat dye. | |
| CH247608A (en) | Process for the production of a vat dye. | |
| CH247607A (en) | Process for the production of a vat dye. | |
| CH247603A (en) | Process for the production of a vat dye. | |
| CH258775A (en) | Process for the preparation of a dye of the anthraquinone series. | |
| CH126822A (en) | Process for the preparation of 2,3-oxynaphthoyl-2'.3'-aminonaphthol methyl ether. |