DE215181C - - Google Patents
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- Publication number
- DE215181C DE215181C DENDAT215181D DE215181DA DE215181C DE 215181 C DE215181 C DE 215181C DE NDAT215181 D DENDAT215181 D DE NDAT215181D DE 215181D A DE215181D A DE 215181DA DE 215181 C DE215181 C DE 215181C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- water
- dyes
- green
- color
- 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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- 239000000975 dye Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 4
- AAAQKTZKLRYKHR-UHFFFAOYSA-N Triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910001369 Brass Inorganic materials 0.000 description 1
- NIKFYOSELWJIOF-UHFFFAOYSA-O Fuchsine Chemical compound Cl.C1=C(N)C(C)=CC(C(=C2C=CC(=[NH2+])C=C2)C=2C=CC(N)=CC=2)=C1 NIKFYOSELWJIOF-UHFFFAOYSA-O 0.000 description 1
- PIJPYDMVFNTHIP-UHFFFAOYSA-L Lead sulfate Chemical compound [PbH4+2].[O-]S([O-])(=O)=O PIJPYDMVFNTHIP-UHFFFAOYSA-L 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- YLZSIUVOIFJGQZ-UHFFFAOYSA-N bis[4-(dimethylamino)phenyl]methanol Chemical compound C1=CC(N(C)C)=CC=C1C(O)C1=CC=C(N(C)C)C=C1 YLZSIUVOIFJGQZ-UHFFFAOYSA-N 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/26—Triarylmethane dyes in which at least one of the aromatic nuclei is heterocyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
PATENTAMTPATENT OFFICE
PATENTSCHRIFTPATENT LETTERING
— M 215181 KLASSE 22 δ. GRUPPE - M 215181 CLASS 22 δ. GROUP
Verfahren zur Darstellung von Triphenylmethanfarbstoffen.Process for the preparation of triphenylmethane dyes.
Patentiert im Deutschen Reiche vom 16. September 1908 ab.Patented in the German Empire on September 16, 1908.
Versuche, das Carbazol in der Technik der Triphenylmethanfarbstoffe zu benutzen (siehe Mühlhäuser, Technik der Rosanilinfarbstoffe i88g, S. 8) sind bisher ohne praktischen Erfolg gewesen. Es wurde nun gefunden, daß wertvolle grüne Säurefarbstoffe erhalten werden, wenn Sulfosäuren des Carbazols, am besten die Di- oder Trisulfosäure, mit Tetralkyldiaminobenzhydrol kondensiert und die Kondensationsprodukte oxydiert werden. Es ist dabei nicht erforderlich, die Sulfosäure abzuscheiden, man kann vielmehr das Sulfierungsgemenge unmittelbar zur Kondensation benutzen.Attempts to use the carbazole in the technique of triphenylmethane dyes (see Mühlhäuser, technique of rosaniline dyes i88g, p. 8) have so far been without practical success. It has now been found that valuable green acid dyes are obtained when sulfonic acids of carbazole are best the di- or trisulfonic acid, with tetralkyldiaminobenzhydrol condensed and the condensation products are oxidized. It is not necessary to separate the sulfonic acid, one can rather use the sulphonation mixture use immediately for condensation.
8,5 kg Carbazol werden bei gewöhnlicher Temperatur in go kg Schwefelsäuremonohydrat eingetragen; die Lösung wird hierauf so lange auf etwa go° C. erwärmt, bis eine Probe, mit Wasser verdünnt, sich nicht mehr trübt. Man kühlt nun auf 20° ab und trägt 13,5 kg Tetramethyldiaminobenzhydrol ein. Dabei hält man die Temperatur unterhalb 500C. Das Gemisch wird so lange auf etwa 50 ° erwärmt, bis das Hydrol verschwunden ist. Man läßt auf gewöhnliche Temperatur abkühlen und rührt es nun in 45 kg Eis und go I Wasser ein; die Leukosulfosäure kristallisiert allmählieh in schneeweißen Nädelchen aus, die sich am Licht rötlich färben. Man läßt 24 Stunden stehen, saugt ab, wäscht mit wenig Wasser, preßt und trocknet bzw. oxydiert direkt als Paste. 12 kg der trockenen Leukosulfosäure werden mittels der erforderlichen Menge Natronlauge in 65 1 Wasser gelöst. Dann werden rasch nacheinander unter star8.5 kg of carbazole are added to kg of sulfuric acid monohydrate at normal temperature; the solution is then warmed to about 0 ° C. until a sample, diluted with water, no longer becomes cloudy. It is then cooled to 20 ° and 13.5 kg of tetramethyldiaminobenzhydrol are introduced. The temperature below 50 0 C. The mixture is kept heated to about 50 ° so long until the Hydrol disappeared. It is allowed to cool to the usual temperature and is then stirred into 45 kg of ice and water; the leucosulfonic acid gradually crystallizes out in snow-white needles that turn reddish in the light. It is left to stand for 24 hours, filtered off with suction, washed with a little water, pressed and dried or oxidized directly as a paste. 12 kg of the dry leucosulfonic acid are dissolved in 65 l of water using the required amount of sodium hydroxide solution. Then quickly one after the other under star
kem Rühren 25 kg Eis und 31 kg Bleisuperoxydpaste, etwa 15,3 Prozent und zuletzt 25 kg 50 prozentige Essigsäure hinzugefügt. Nach erfolgter Oxydation wird eine Lösung von 4 kg Natriumsulfat in 20 1 Wasser hinzugesetzt und das Gemisch auf 60 ° angewärmt. Sobald das Bleisulfat sich abgesetzt hat, wird abfiltriert und das Filtrat mit Kochsalz gesättigt. Der Farbstoff fällt in Form messingglänzender Kriställchen aus, die abgesaugt, mit Salzwasser gewaschen und getrocknet werden; sie bilden dann ein kupferglänzendes Kristallpulver, das sich in Wasser leicht mit grüner Farbe löst; die Farbe dieser Lösung wird durch konzentriertes Ammoniak nicht verändert. In heißem Alkohol löst sich der Farbstoff mit blaugrüner, in konzentrierter Schwefelsäure mit blaßgelber Farbe. Wolle wird in saurem Bade grün älkaliecht gefärbt; die Bäder werden vollständig erschöpft.Without stirring 25 kg of ice and 31 kg of lead peroxide paste, about 15.3 percent and finally 25 kg 50 percent acetic acid added. After oxidation has taken place, a solution of 4 kg of sodium sulfate in 20 l of water were added and the mixture was warmed to 60 °. As soon as the lead sulfate has settled, it is filtered off and the filtrate is saturated with common salt. The dye precipitates in the form of shiny brass crystals, which are sucked off with salt water to be washed and dried; they then form a shiny copper crystal powder, which easily dissolves in water with a green color; the color of this solution will be not changed by concentrated ammonia. In hot alcohol the dye dissolves with blue-green in concentrated sulfuric acid with pale yellow color. Wool is dyed green alkali in an acid bath; the Baths become completely exhausted.
Tetraäthyldiaminobenzhydrol gibt einen gelbstichigeren Farbstoff von analogen Eigenschaften, welcher sich in konzentrierter Schwefelsäure mit schmutzig violetter Farbe löst.Tetraäthyldiaminobenzhydrol gives a more yellowish dye with analogous properties, which dissolves in concentrated sulfuric acid with a dirty purple color.
Die so erhaltenen Farbstoffe sind von außerordentlicher Intensität und vorzüglicher Echtheit gegen Wäsche, .Licht, schweflige Säure und Dekatur. Besonders hervorzuheben ist ferner ihr Egalisierungsvermögen.The dyes obtained in this way are of extraordinary intensity and excellent fastness against laundry, light, sulphurous acid and decatur. Particularly noteworthy is also their ability to equalize.
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DE215181C true DE215181C (en) |
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ID=476704
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Country Status (1)
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- DE DENDAT215181D patent/DE215181C/de active Active
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