CH160959A - Process for the production of a vat dye of the anthraquinone series. - Google Patents
Process for the production of a vat dye of the anthraquinone series.Info
- Publication number
- CH160959A CH160959A CH160959DA CH160959A CH 160959 A CH160959 A CH 160959A CH 160959D A CH160959D A CH 160959DA CH 160959 A CH160959 A CH 160959A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- mol
- dye
- anthraquinone series
- production
- Prior art date
Links
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 title claims description 5
- 150000004056 anthraquinones Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 3
- 239000000984 vat dye Substances 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 6
- FBMQNRKSAWNXBT-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2N FBMQNRKSAWNXBT-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 240000007817 Olea europaea Species 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KXEWYGIZIZYGDL-UHFFFAOYSA-N 1,3-dibromoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Br)=CC(Br)=C3C(=O)C2=C1 KXEWYGIZIZYGDL-UHFFFAOYSA-N 0.000 description 1
- ZQNAPBOSLCTZIB-UHFFFAOYSA-N 1,3-dichloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC(Cl)=C3C(=O)C2=C1 ZQNAPBOSLCTZIB-UHFFFAOYSA-N 0.000 description 1
- PTQPMJPRFVZVQO-UHFFFAOYSA-N 3-bromo-1-chloroanthracene-9,10-dione Chemical compound ClC1=CC(=CC=2C(C3=CC=CC=C3C(C12)=O)=O)Br PTQPMJPRFVZVQO-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001049 brown dye Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/26—Carbazoles of the anthracene series
- C09B5/28—Anthrimide carbazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 156755. Verfahren zur Herstellung eines Nüpenfar bstoifes der Anthrachinonr eihe. Es wurde gefunden, dass man einen neuen Küpenfarbstoff der Anthrachinonreihe er hält, wenn man auf 9 Mol. 1,3-Dihalogen- anthrachinon nacheinander 1 Mol. 1,4-Di- aminoanthrachinon und 2 Mol. 1,
4-Mono- benzoyldia.minoanthrachinon einwirken lässt iznd hierauf das erhaltene Produkt mit einem sauren Kondensationsmittel behandelt.
Der neue Farbstoff stellt ein dunkles Pulver dar, das sich in konzentrierter Schwe felsäure mit olivbrauner Farbe löst und Baumwolle aus der Küpe in kräftigen und sehr echten oliven Tönen färbt.
<I>Beispiel:</I> 23,8 Teile 1,4-Diaminoanthrachinon, 74 Teile 1,3-Dibromanthrachinon, 25 Teile was serfreies Natriumacetat, 1 Teil Kupferacetat und<B>800</B> Teile Nitrobenzol werden 10 Stun den zum Sieden erhitzt. Das Umsetzungs produkt wird kalt abfiltriert, mit Nitro- benzol, dann mit Alkohol gewaschen, hier auf mit Wasser ausgekocht und getrocknet.
20 Teile der so erhaltenen Verbindung, die noch etwa 16% Brom enthält, werden nun mit 20 Teilen 1,4-Monobenzoyldiamino- anthrachinon, 5 Teilen wasserfreiem Na triumacetat, 10 Teilen Natriumkarbonat, 1 Teil Kupferchlorür und 400 Teilen Nitro- benzol 24 Stunden zum Sieden erhitzt. Das Umsetzungsprodukt wird bei etwa<B>80'</B> ab filtriert, mit Nitrobenzol, dann mit Alkohol gewaschen, hierauf mit Wasser und wenig verdünnter .Salpetersäure ausgekocht, filtriert und getrocknet.
Durch Aufkochen mit Nitro- benzol und heisser Filtration wird es vom überschüssigen 1,4 - Monobenzoyldiaminoan- thraehinon befreit. Es löst sich in Mono hydrat mit grasgrüner Farbe.
10 Teile dieser Verbindung werden nun bei etwa 100 in eine Schmelze eingetragen, die erhalten wird, indem 20 Teile wasser freies Aluminiumchlorid derart zu 40 Teilen Pyridin gegeben werden, dass die Temperatur <B>100'</B> nicht wesentlich übersteigt. Hierauf wird die Temperatur bis zum schwachen Sie- den des Pyridins gesteigert. Nach einer Stunde wird die Schmelze auf eine alkalische Natriumhydnosulfitlösung ausgetragen, wo bei der neue Farbstoff mit gelbbrauner Farbe in Lösung geht. Durch kräftiges Umrüh ren an der Luft bei gewöhnlicher Temperatur wird der Farbstoff abgeschieden und abfil- triert.
Zu demselben Farbstoffe gelangt man, wenn statt 1;3-Dibromanthrachinon das 1,3 Dichloranthrachinon oder das 1-Chlor-3- bromanthrachinon verwendet wird.
Ebenso wird dasselbe Resultat erhalten, wenn das Natriumacetat durch Kaliumacetat oder kalzinierte Alkalikarbonate oder Mag nesiumoxyd und das Kupferacetat oder Kupferchlorür durch andere Kupferverbin dungen oder metallisches Kupfer ersetzt wird. Endlich wird ebenfalls dasselbe Resultat er- halten, wenn als Lösungsmittel statt Nitro- benzol Naphthalin verwendet wird.
Additional patent to the main patent No. 156755. Process for the production of a Nüpenfar bstoifes of the anthraquinone series. It has been found that a new vat dye of the anthraquinone series is obtained if 1 mol. 1,4-di-aminoanthraquinone and 2 mol.
4-Monobenzoyldia.minoanthraquinone is allowed to act and the product obtained is then treated with an acidic condensing agent.
The new dye is a dark powder that dissolves in concentrated sulfuric acid with an olive-brown color and dyes cotton from the vat in strong and very genuine olive tones.
<I> Example: </I> 23.8 parts 1,4-diaminoanthraquinone, 74 parts 1,3-dibromoanthraquinone, 25 parts anhydrous sodium acetate, 1 part copper acetate and <B> 800 </B> parts nitrobenzene are 10 hours heated to the boil. The reaction product is filtered off cold, washed with nitrobenzene, then with alcohol, here boiled up with water and dried.
20 parts of the compound thus obtained, which still contains about 16% bromine, are now trium acetate with 20 parts of 1,4-monobenzoyldiamino anthraquinone, 5 parts of anhydrous sodium, 10 parts of sodium carbonate, 1 part of copper chloride and 400 parts of nitrobenzene for 24 hours Boiling heated. The reaction product is filtered off at about <B> 80 '</B>, washed with nitrobenzene and then with alcohol, then boiled with water and a little dilute nitric acid, filtered and dried.
It is freed from excess 1,4-monobenzoyldiaminoanthraehinone by boiling with nitrobenzene and hot filtration. It dissolves in monohydrate with a grass green color.
10 parts of this compound are then introduced into a melt at about 100, which is obtained by adding 20 parts of anhydrous aluminum chloride to 40 parts of pyridine in such a way that the temperature does not significantly exceed 100 '. The temperature is then increased until the pyridine boils slowly. After one hour, the melt is poured onto an alkaline sodium hydnosulfite solution, where the new yellow-brown dye dissolves. The dye is deposited and filtered off by vigorous stirring in the air at normal temperature.
The same dye is obtained if 1,3 dichloroanthraquinone or 1-chloro-3-bromoanthraquinone is used instead of 1; 3-dibromoanthraquinone.
Likewise, the same result is obtained if the sodium acetate is replaced by potassium acetate or calcined alkali metal carbonates or magnesium oxide and the copper acetate or copper chloride by other copper compounds or metallic copper. Finally, the same result is also obtained if naphthalene is used as solvent instead of nitrobenzene.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH160959D CH160959A (en) | 1931-07-02 | 1931-07-02 | Process for the production of a vat dye of the anthraquinone series. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH160959D CH160959A (en) | 1931-07-02 | 1931-07-02 | Process for the production of a vat dye of the anthraquinone series. |
| CH156755T | 1931-07-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH160959A true CH160959A (en) | 1933-03-31 |
Family
ID=25716837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH160959D CH160959A (en) | 1931-07-02 | 1931-07-02 | Process for the production of a vat dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH160959A (en) |
-
1931
- 1931-07-02 CH CH160959D patent/CH160959A/en unknown
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