CH169352A - Process for the production of a new black coloring sulfur dye. - Google Patents
Process for the production of a new black coloring sulfur dye.Info
- Publication number
- CH169352A CH169352A CH169352DA CH169352A CH 169352 A CH169352 A CH 169352A CH 169352D A CH169352D A CH 169352DA CH 169352 A CH169352 A CH 169352A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- dye
- sulfur dye
- sulfur
- new
- Prior art date
Links
- 239000000975 dye Substances 0.000 claims description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 238000004040 coloring Methods 0.000 claims description 3
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000988 sulfur dye Substances 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- YRUPBAWWCPVHFT-UHFFFAOYSA-N 4-(4-hydroxyanilino)phenol Chemical compound C1=CC(O)=CC=C1NC1=CC=C(O)C=C1 YRUPBAWWCPVHFT-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- NQRLPDFELNCFHW-UHFFFAOYSA-N nitroacetanilide Chemical compound CC(=O)NC1=CC=C([N+]([O-])=O)C=C1 NQRLPDFELNCFHW-UHFFFAOYSA-N 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JSTCPNFNKICNNO-UHFFFAOYSA-N 4-nitrosophenol Chemical compound OC1=CC=C(N=O)C=C1 JSTCPNFNKICNNO-UHFFFAOYSA-N 0.000 description 1
- BNOODXBBXFZASF-UHFFFAOYSA-N [Na].[S] Chemical compound [Na].[S] BNOODXBBXFZASF-UHFFFAOYSA-N 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- RSAZYXZUJROYKR-UHFFFAOYSA-N indophenol Chemical compound C1=CC(O)=CC=C1N=C1C=CC(=O)C=C1 RSAZYXZUJROYKR-UHFFFAOYSA-N 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides 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
- C09B49/00—Sulfur dyes
- C09B49/10—Sulfur dyes from diphenylamines, indamines, or indophenols, e.g. p-aminophenols or leucoindophenols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Photoreceptors In Electrophotography (AREA)
Description
Verfahren zur Herstellung eines neuen schwarz färbenden Schwefelfarbstoffes. Es wurde gefunden, dass man einen neuen schwarz färbenden Schwefelfarbstoff erhält, wenn man das Leukoindopheriol aus Carbazol und p-Nitrosophenol in Gegenwart von p- Aminoacetanilid oberhalb 2000 schwefelt. Das p-Aminoacetanilid kann selbstverständlich durch solche Produkte ersetzt werden, die unterdenSchweflungsbedingungeninp-Amino- acetanilid übergeführt werden, wie z. B. p- Nitroacetanilid.
Der neue Farbstoff bildet ein dunkles Pulver, löst sich in Schwefelsäure mit blau grüner Farbe und färbt Baumwolle aus schwefelnatriumhaltigem Bade in echten tief schwarzen Tönen.
<I>Beispiel<B>1:</B></I> <B>16,7</B> gr Carbazol werden in bekannter Weise mit 14,5 Teilen p-Niti-osopheziol kon densiert, das gebildete Indophenol durch Aus tragen in Eiswasser isoliert und filtriert. Hierauf wird es durch Behandeln mit einer Polysulfidlösung aus<B>36</B> Teilen kristallisiertem Schwefelnatrium und 14,5 Teilen Schwefel reduziert. Nach der Reduktion gibt man der Masse noch<B>8</B> Teile 1-Aoetylamino-4-amino- benzol, <B>15,5</B> Teile Schwefel und<B>10</B> Teile Kochsalz zu. Hierauf wird getrocknet und bei 210-2150 so lange erwärmt, bis kein Schwefelwasserstoff mehr entweicht.
Die erhaltene, fein gepulverte Schmelze wird in 2 Liter Wasser eingetragen und mit Luft oxydiert, bis kein gelöster Farbstoff mehr nachweisbar ist. Hierauf wird der Farbstöff filtriert und getrocknet.
<I>Beispiel 2:</I> Das nachBeispiel <B>1</B> hergestellte Indopheriol wird in einer Mischung von<B>29</B> gr Schwefel natrium und 12 gr Schwefel reduziert. Nach Zusatz von 14 Teilen 1-Acetylainino-4-auaino- benzol, <B>23</B> Teilen Schwefel und<B>10</B> Teilen Kochsalz wird getrocknet, gemahlen und auf 230-240<B>0</B> erwärmt, bis keine Schwefelwasser- stoffentwicklung mehr stattfindet.
Hierauf wird die erhaltene fein gepulverte Masse in 2 Liter warmes Wasser eingetragen und mit verdünnter Schwefelsäure ausgesäuert. Der vollständig abgeschiedene Farbstoff wird filtriert und getrocknet.
Zum gleichen Resultate gelangt man, wenn man das 1-Acetylamino-4-aminobenzol durch das 1-Acetylamino-4-nitrobenzol ersetzt.
Process for the production of a new black coloring sulfur dye. It has been found that a new black-coloring sulfur dye is obtained if the leucoindopheriol from carbazole and p-nitrosophenol is sulfurized above 2000 in the presence of p-aminoacetanilide. The p-aminoacetanilide can of course be replaced by those products which are converted to p-aminoacetanilide under the sulphurisation conditions, such as e.g. B. p-nitroacetanilide.
The new dye forms a dark powder, dissolves in sulfuric acid with a blue-green color and dyes cotton from baths containing sodium sulphide in real deep black tones.
<I> Example <B>1:</B> </I> <B> 16.7 </B> gr carbazole are condensed in a known manner with 14.5 parts of p-niti-osopheziol, the indophenol formed through Isolated from wear in ice water and filtered. It is then reduced by treatment with a polysulfide solution composed of 36 parts of crystallized sodium sulphide and 14.5 parts of sulfur. After the reduction, <B> 8 </B> parts of 1-aoetylamino-4-aminobenzene, <B> 15.5 </B> parts of sulfur and <B> 10 </B> parts of common salt are added to the mass to. It is then dried and heated at 210-2150 until no more hydrogen sulfide escapes.
The finely powdered melt obtained is poured into 2 liters of water and oxidized with air until no more dissolved dye can be detected. The dye is then filtered and dried.
<I> Example 2: </I> The indopheriol produced according to example <B> 1 </B> is reduced in a mixture of <B> 29 </B> g of sodium sulfur and 12 g of sulfur. After adding 14 parts of 1-acetylainino-4-auainobenzene, 23 parts of sulfur and 10 parts of sodium chloride, the mixture is dried, ground and reduced to 230-240 parts / B> heated until no more hydrogen sulphide evolution occurs.
The finely powdered mass obtained is then introduced into 2 liters of warm water and acidified with dilute sulfuric acid. The completely deposited dye is filtered and dried.
The same result is obtained if 1-acetylamino-4-aminobenzene is replaced by 1-acetylamino-4-nitrobenzene.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH169352T | 1934-04-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH169352A true CH169352A (en) | 1934-05-31 |
Family
ID=4421473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH169352D CH169352A (en) | 1934-04-19 | 1933-05-17 | Process for the production of a new black coloring sulfur dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH169352A (en) |
-
1933
- 1933-05-17 CH CH169352D patent/CH169352A/en unknown
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