CH176236A - Process for the production of a nitrogenous vat dye of the anthraquinone series. - Google Patents
Process for the production of a nitrogenous vat dye of the anthraquinone series.Info
- Publication number
- CH176236A CH176236A CH176236DA CH176236A CH 176236 A CH176236 A CH 176236A CH 176236D A CH176236D A CH 176236DA CH 176236 A CH176236 A CH 176236A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- production
- vat
- nitrogenous
- vat dye
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims description 4
- 239000000984 vat dye Substances 0.000 title claims description 3
- 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 description 3
- 150000004056 anthraquinones Chemical class 0.000 title description 3
- 239000000975 dye Substances 0.000 claims description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000007859 condensation product Substances 0.000 claims description 5
- NGGBYCPITQNVGN-UHFFFAOYSA-N 1-chloro-10h-anthracen-9-one Chemical compound C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl NGGBYCPITQNVGN-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 229940015043 glyoxal Drugs 0.000 claims description 3
- FWEQPMZEKHHFTB-UHFFFAOYSA-N n-(5-amino-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=CC=C2C(=O)C=3C(N)=CC=CC=3C(=O)C2=C1NC(=O)C1=CC=CC=C1 FWEQPMZEKHHFTB-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 claims description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Coloring (AREA)
Description
Verfahren zur Herstellung eines stickstoffhaltigen hüpenfarbstoffes der Anthrachinonreihe. Vorliegendes Patent bezieht sich auf ein Verfahren zur Herstellung .eines stickstoff haltigen Küpenfarbstoffes der Anthrachinon- reihe, dadurch gekennzeichnet, dass man 1 Mol des Kondensationsproduktes, das durch Einwirkung eines sauren Kondensationsmit tels auf das Kondensationsprodukt von 1 Chloranthron mit Glyoxalsulfat erhalten wird,
mit 2 Mol 1-Amino-5-benzoylamino- anthrachinon umsetzt und das so erhaltene Umsetzungsprodukt einer Behandlung mit einem Kondensationsmittel unterwirft. Das Kondensationsmittel tritt dabei nicht in den Endstoff ein.
Der neue Farbstoff löst sich in konzen- tierter Schwefelsäure rein blau und gibt auf Formaldehydzusatz keine Farbänderung mehr. Er färbt Baumwolle aus braunroter Küpe in kräftigen dunkelbraunen Tönen an, die die Färbungen des nicht nachbehandelten Farbstoffeq an Klarheit der Nüance und in der Chlorechtheit übertreffen.
<I>Beispiel:</I> 48 Teile des Kondensationsproduktes aus 1-Chloranthron und Glyoxalsulfat und 75 Teile 1-Amino - 5 -benzoylamino-anthrachinon werden zusammen mit 20 Teilen Pottasche und 5 Teilen Kupferoxyd in 500 Teilen Naphthalin etwa 6 Stunden auf 2.00 bis 210' C erhitzt und wie üblich aufgearbeitet. Man erhält ein dunkelbraunes kristallinisches Farbstoffpulver, das sich mit dunkelrotviolet- ter Farbe verküpen lässt und Baumwolle in dunkelbraunen, sehr echten Tönen anfärbt.
In konzentrierter Schwefelsäure löst sich die Substanz dichroitisch blaurot. Die Nach behandlung kann zum Beispiel wie folgt ge schehen: 10 Teile des Farbstoffes werden in etwa 2.50 Teilen Chlorsulfonsäure bei Raumtempe ratur 12 Stunden gerührt und dann auf Eis gegeben. Der entstandene Niederschlag wird in üblicher Weise isoliert.
Process for the production of a nitrogen-containing coat dye of the anthraquinone series. The present patent relates to a process for the production of a nitrogen-containing vat dye of the anthraquinone series, characterized in that 1 mol of the condensation product obtained by the action of an acidic condensation agent on the condensation product of 1 chloranthrone with glyoxal sulfate is added,
reacted with 2 moles of 1-amino-5-benzoylamino anthraquinone and the resulting reaction product subjected to a treatment with a condensing agent. The condensation agent does not enter the end product.
The new dye dissolves in concentrated sulfuric acid in a pure blue color and no longer changes color when formaldehyde is added. It dyes cotton from a reddish brown vat in strong dark brown tones that surpass the colorations of the untreated dyes in terms of clarity, nuance and chlorine fastness.
<I> Example: </I> 48 parts of the condensation product of 1-chloranthrone and glyoxal sulfate and 75 parts of 1-amino-5-benzoylamino-anthraquinone are combined with 20 parts of potash and 5 parts of copper oxide in 500 parts of naphthalene for about 6 hours at 2:00 am Heated to 210 ° C and worked up as usual. A dark brown crystalline dye powder is obtained which can be vat with a dark red-violet color and dyes cotton in dark brown, very genuine shades.
The substance dissolves in a dichroic bluish red color in concentrated sulfuric acid. The aftertreatment can, for example, proceed as follows: 10 parts of the dye are stirred in about 2.50 parts of chlorosulfonic acid at room temperature for 12 hours and then poured onto ice. The resulting precipitate is isolated in the usual way.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE176236X | 1932-09-07 | ||
| CH170452T | 1933-07-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH176236A true CH176236A (en) | 1935-03-31 |
Family
ID=25718933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH176236D CH176236A (en) | 1932-09-07 | 1933-07-28 | Process for the production of a nitrogenous vat dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH176236A (en) |
-
1933
- 1933-07-28 CH CH176236D patent/CH176236A/en unknown
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