DE272843C - - Google Patents
Info
- Publication number
- DE272843C DE272843C DENDAT272843D DE272843DA DE272843C DE 272843 C DE272843 C DE 272843C DE NDAT272843 D DENDAT272843 D DE NDAT272843D DE 272843D A DE272843D A DE 272843DA DE 272843 C DE272843 C DE 272843C
- Authority
- DE
- Germany
- Prior art keywords
- dyes
- benzidine
- sulfur
- acids
- sulfonic acids
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- -1 naphthylamine sulfonic acids Chemical class 0.000 claims description 7
- HFACYLZERDEVSX-UHFFFAOYSA-N Benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 238000007792 addition Methods 0.000 claims description 5
- 239000000988 sulfur dye Substances 0.000 claims description 5
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-Aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 4
- 239000007859 condensation product Substances 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- JSTCPNFNKICNNO-UHFFFAOYSA-N 4-nitrosophenol Chemical compound OC1=CC=C(N=O)C=C1 JSTCPNFNKICNNO-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 230000000875 corresponding Effects 0.000 claims 1
- 239000000975 dye Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 230000001590 oxidative Effects 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 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
- 241000054817 Lycaena dione Species 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N Sodium sulfide Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000000853 cresyl group Chemical class C1(=CC=C(C=C1)C)* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000001046 green dye Substances 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- JVI 272843 KLASSE 22«?. GRUPPE- JVI 272843 CLASS 22 «?. GROUP
Verfahren zur Herstellung von Schwefelfarbstoffen.Process for the production of sulfur dyes.
Patentiert im Deutschen Reiche vom 14. März 1911 ab.Patented in the German Empire on March 14, 1911.
Es wurde gefunden, daß die Indophenolsulfosäuren, welche man durch Kondensation von Nitrosophenol oder dessen Substitutionsprodukten oder durch Oxydation von p-Aminophenol oder dessen Substitutionsprodukten mit den Kondensationsprodukten aus Benzidin und Naphtylaminsulfosäuren erhalten kann, in der Schwefelschmelze zu wertvollen Schwefelfarbstoffen führen.It has been found that the indophenolsulfonic acids, which are obtained by condensation by nitrosophenol or its substitution products or by oxidation of p-aminophenol or its substitution products with the condensation products of benzidine and Naphthylamine sulfonic acids can be obtained in the sulfur melt to form valuable sulfur dyes to lead.
ίο Die diesen neuen Indophenolsulfosäuren zugrunde liegenden Kondensationsprodukte werden durch Verschmelzen von Benzidin einerseits, mit Naphtylaminsulfosäuren (z.B. 1-7-, 1-8-, ι ■ 2-Naphtylaminsulfosäure, 1 · 4 · 8-Naphtylamindisulfosäure und sonstigen) anderseits, mit oder ohne Zusatz eines Lösungsoder Suspensionsmittes, dargestellt, so z. B. in der Weise, daß man 44,6 kg i-Naphtylamin-8-sulfosäure und 55,2 kg Benzidin miteinander erhitzt und die erkaltete Schmelze in fein gepulvertem Zustand durch mehrfache Behandlung mit kochender Sodalösung und Ausfällen der kochenden Lösung mit verdünnter Salzsäure vom beigemengten Benzidin und i-Naph- tylamin-8-sulfosäure befreit.ίο The basis of these new indophenol sulfonic acids lying condensation products are produced by fusing benzidine on the one hand, with naphthylamine sulfonic acids (e.g. 1-7-, 1-8-, ι ■ 2-naphthylamine sulfonic acid, 1x4x8-naphthylamine disulfonic acid and other) on the other hand, with or without the addition of a solvent or suspending agent, shown, e.g. Am the way that you 44.6 kg of i-naphthylamine-8-sulfonic acid and 55.2 kg of benzidine are heated together and the cooled melt in a finely powdered state by multiple treatments with boiling soda solution and precipitation of the boiling solution with dilute hydrochloric acid from the added benzidine and i-naph- tylamine-8-sulfonic acid freed.
Die Herstellung der Indophenolsulfosäuren erfolgt in üblicher Weise durch Zusammenoxydieren von p-Aminophenol oder dessen Substitutionsprodukten mit den vorerwähnten Sulfosäuren; sie stellen in Wasser unlösliche, in verdünnter Natronlauge lösliche Körper dar. Die Schwefelschmelze mittels derselben kann mit Alkalipolysulfid in verschiedenen Verhältnissen mit oder ohne Zusatz eines Verdünnungsmittels (Wasser, Alkohol, Glycerin, Phenol, Kresol usw. bzw. Metallsalzes, z. B. eines Kupfersalzes) bei wechselnden Temperaturen ausgeführt werden. Der Kupferzusatz erweist sich als besonders vorteilhaft zur Erzeugung grüner Farbstoffe, während ohne Kupferzusatz mehr blaue bis grünblaue Farbstoffe erhalten werden.The indophenol sulfonic acids are prepared in the usual way by oxidizing p-aminophenol or its substitution products with the aforementioned sulfonic acids; They represent bodies that are insoluble in water and soluble in dilute sodium hydroxide solution. The molten sulfur can be mixed with alkali polysulphide in various proportions with or without the addition of a diluent (water, alcohol, glycerine, phenol, cresol, etc. or a metal salt, e.g. Copper salt) at changing temperatures. The addition of copper has proven particularly advantageous for the generation of green dyes, whereas without Kup erzusatz f more blue to green can be obtained blue dyes.
100 kg der durch Zusammenoxydieren von p-Aminophenol mit dem Kondensationsprodukt aus Benzidin und 1 · 8-N aphtylaminsulfosäure erhaltenen Rohindophenolsulfosäure werden in eine wäßrige Polysulfidlösung, bestehend aus 800 kg Schwefelnatrium, 500 kg Schwefel, eingetragen und mit oder ohne Zusatz von etwa 50 kg Kupfervitriol ungefähr 30 Stunden am Rückflußkühler zum Kochen erhitzt. Die Schmelze ist dann beendet, wenn sich in der Schmelze keine Indophenolsulfosäure mehr nachweisen läßt.100 kg by oxidizing p-aminophenol together with the condensation product Crude indophenol sulfonic acid obtained from benzidine and 1 × 8-N aphtylaminsulfosäure are in an aqueous polysulphide solution consisting of 800 kg of sodium sulfur, 500 kg of sulfur, entered and with or without the addition of about 50 kg of vitriol for about 30 hours The reflux condenser heated to the boil. The melt is ended when the Indophenolsulfonic acid can no longer be detected in the melt.
Die Isolierung des Farbstoffes erfolgt nach den bei Schwefelfarbstofien üblichen Methoden, z. B. durch Auslaugen, Ausblasen oder Ausfällen mit Säure, Abpressen und Trocknen.The dye is isolated by the methods customary for sulfur dyes, z. B. by leaching, blowing or precipitation with acid, pressing and drying.
Der so erhaltene Farbstoff stellt in reinem Zustande ein metallglänzendes, grünblaues Pulver dar, welches sich in Schwefelnatrium mit gelblicher Farbe leicht löst und daraus Baumwolle in schönen klaren, grünen Tönen anfärbt, die durch besondere Waschechtheit gegenüber. den Farbstoffen der Patentschrift 162156 ausgezeichnet sind. Auch die Lichtechtheit ist eine ganz hervorragende.In its pure state, the dye obtained in this way is a shiny metal, green-blue powder which is dissolved in sodium sulphide easily dissolves yellowish color and dyes cotton in beautiful clear, green tones from it, those due to special washfastness. awarded the dyes of patent specification 162156 are. The lightfastness is also very good.
Auf dieselbe Weise lassen sich auch die übrigen Schwefelfarbstoffe dieser neuen Klasse herstellen. Dieselben zeichnen sich durchThe other sulfur dyes of this new class can also be used in the same way produce. The same are characterized by
ihre leichte Löslichkeit bei sehr guter Waschechtheit aus.their easy solubility and very good wash fastness.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE272843C true DE272843C (en) |
Family
ID=529357
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT272843D Active DE272843C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE272843C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE742812C (en) * | 1938-02-17 | 1943-12-17 | Ig Farbenindustrie Ag | Process for the production of sulfur dyes |
| US7151101B2 (en) * | 1998-06-12 | 2006-12-19 | Vertex Pharmaceuticals Incorporated | Inhibitors of p38 |
-
0
- DE DENDAT272843D patent/DE272843C/de active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE742812C (en) * | 1938-02-17 | 1943-12-17 | Ig Farbenindustrie Ag | Process for the production of sulfur dyes |
| US7151101B2 (en) * | 1998-06-12 | 2006-12-19 | Vertex Pharmaceuticals Incorporated | Inhibitors of p38 |
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