CH133807A - Process for the preparation of a vat dye of the anthanthrone series. - Google Patents
Process for the preparation of a vat dye of the anthanthrone series.Info
- Publication number
- CH133807A CH133807A CH133807DA CH133807A CH 133807 A CH133807 A CH 133807A CH 133807D A CH133807D A CH 133807DA CH 133807 A CH133807 A CH 133807A
- Authority
- CH
- Switzerland
- Prior art keywords
- catalytically active
- preparation
- acid
- vat dye
- copper
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- PGEHNUUBUQTUJB-UHFFFAOYSA-N anthanthrone Chemical class C1=CC=C2C(=O)C3=CC=C4C=CC=C5C(=O)C6=CC=C1C2=C6C3=C54 PGEHNUUBUQTUJB-UHFFFAOYSA-N 0.000 title claims description 5
- 239000000984 vat dye Substances 0.000 title claims description 4
- 239000013543 active substance Substances 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 2
- 239000005749 Copper compound Substances 0.000 claims 1
- 150000001880 copper compounds Chemical class 0.000 claims 1
- 239000000975 dye Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 description 3
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 2
- PXNNPGGYHAWDJW-UHFFFAOYSA-N N-(4-amino-9,10-dioxo-1-anthracenyl)benzamide Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=CC=C1NC(=O)C1=CC=CC=C1 PXNNPGGYHAWDJW-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical group [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahre zur Darstellung eines Küpenfarbstoffes der Anthanthronreihe. Es wurde gefunden, dass man in halo- geniertem Anthanthron bezw. seinen Deri vaten und Substitutionsprodukten die Ha logenatome ganz oder teilweise durch Aminoanthrachinone bezw. ihre Derivate ersetzen kann.
Man verfährt dabei derart, dass man Halo:genauthanthrone mit Amino- anthrachinonen bei Gegenwart von säure bindenden Mitteln, wie wasserfreiem Na triumacetat, und katalytisch wirkenden Stof fen, wie Kupfer oder Kupfersalzen bezw. Verbindungen erhitzt.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung eines neuen Küpenfarbstoffes der Anthanthronreihe, da durch gekennzeichnet, dass man 1 Hol. Di- halogenanthanthron, hergestellt aus 1.1'- Dinaphtyl - 4. 4'- dihalogen - 8. 8'- dicarbon- säure, mit ,2 Hol.
1-Benzoylamino-4-amino- anthrachinon bei Gegenwart von säure bindenden Mitteln und katalytisch wirken den Substanzen kondensiert. Als Katalyten kann man zum Beispiel geringe Mengen Kupfer oder seine Verbin dungen und Salze nehmen.
Eeispieli: 4;6 Gewichtsteile synthetisches Dibrom- anthanthron, hergestellt aus 1.1'-Dinaph- tyl-4.4'-dibrom-8.8'-dicarbonsäure werden in 150 Gewichtsteilen Naphtalin mit 2,6 Ge wichtsteilen Natriumacetat, 0,5 Gewichts teilen Kupferacetat und 8 Gewichtsteilen 1-Benzoylamino-4-aminoanthrachinon einige Stunden zum Kochen erhitzt.
Die etwas er kaltete, aber noch flüssige Schmelze wird mit heisser Solventnaphta oder einem andern geeigneten Lösungsmittel verdünnt, abge saugt, mit heisser Solventnaphta, dann hei ssem Alkohol nachgewaschen, der dunkle Rückstand zur Entfernung der anorga nischen Salze mit verdünnter Salzsäure ausgekocht und getrocknet.
Man erhält so mikroskopische blaugraue Nadelehen, die in. konzentrierter Schwefelsäure gelbstickig grün löslich 'sind, aus dieser Lösung mit Wasser grünsticbig blaue Flocken abschei den und auf Baumwolle aus stumpf wein roter güpe schön grünstickig blau mit sehr guten Echtheitseigenschaften auffärben.
Proceed to the representation of a vat dye of the anthanthrone series. It has been found that in halogenated anthanthrone or. its derivatives and substitution products, the halogen atoms wholly or partly by aminoanthraquinones respectively. can replace their derivatives.
The procedure is that Halo: genauthanthrones with amino anthraquinones in the presence of acid-binding agents, such as anhydrous sodium acetate, and catalytically active substances, such as copper or copper salts or. Connections heated.
The subject of the present patent is a process for the preparation of a new vat dye of the anthanthrone series, characterized in that one Hol. Di-halogenanthanthrone, made from 1.1'-dinaphthyl - 4. 4'-dihalogen - 8. 8'-dicarboxylic acid, with, 2 hol.
1-Benzoylamino-4-amino-anthraquinone in the presence of acid-binding agents and catalytically act the substances condensed. Small amounts of copper or its compounds and salts can be used as a catalyst.
Examplei: 4; 6 parts by weight of synthetic dibromanthanthrone, prepared from 1.1'-dinaphthyl-4.4'-dibromo-8.8'-dicarboxylic acid are mixed in 150 parts by weight of naphthalene with 2.6 parts by weight of sodium acetate, 0.5 parts by weight of copper acetate and 8 Parts by weight of 1-benzoylamino-4-aminoanthraquinone heated to the boil for a few hours.
The slightly cold, but still liquid melt is diluted with hot solvent naphtha or another suitable solvent, filtered off with suction, washed with hot solvent naphtha, then hot alcohol, the dark residue is boiled with dilute hydrochloric acid to remove the inorganic salts and dried.
This gives microscopic blue-gray needles which are soluble in concentrated sulfuric acid in a yellowish green color, from this solution with water they separate greenish blue flakes and on cotton from a dull wine red güpe they color a beautiful greenish blue with very good fastness properties.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE133807X | 1927-03-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH133807A true CH133807A (en) | 1929-06-30 |
Family
ID=5665169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH133807D CH133807A (en) | 1927-03-08 | 1928-02-24 | Process for the preparation of a vat dye of the anthanthrone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH133807A (en) |
-
1928
- 1928-02-24 CH CH133807D patent/CH133807A/en unknown
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