DE71370C - Process for the preparation of blue basic dyes of the triphenylmethane series from dichlorobenzaldehyde - Google Patents
Process for the preparation of blue basic dyes of the triphenylmethane series from dichlorobenzaldehydeInfo
- Publication number
- DE71370C DE71370C DENDAT71370D DE71370DA DE71370C DE 71370 C DE71370 C DE 71370C DE NDAT71370 D DENDAT71370 D DE NDAT71370D DE 71370D A DE71370D A DE 71370DA DE 71370 C DE71370 C DE 71370C
- Authority
- DE
- Germany
- Prior art keywords
- dye
- dichlorobenzaldehyde
- peroxide
- blue
- lead
- 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.)
- Expired - Lifetime
Links
- LLMLNAVBOAMOEE-UHFFFAOYSA-N 2,3-dichlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1Cl LLMLNAVBOAMOEE-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 239000000981 basic dye Substances 0.000 title claims description 3
- 150000004961 triphenylmethanes Chemical class 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-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
- 239000000975 dye Substances 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- MWOUGPLLVVEUMM-UHFFFAOYSA-N N-ethyl-2-methylaniline Chemical compound CCNC1=CC=CC=C1C MWOUGPLLVVEUMM-UHFFFAOYSA-N 0.000 claims description 2
- VXMKYRQZQXVKGB-CWWHNZPOSA-N Tannin Chemical compound O([C@H]1[C@H]([C@@H]2OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)O[C@H]([C@H]2O)O1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 VXMKYRQZQXVKGB-CWWHNZPOSA-N 0.000 claims description 2
- 210000002268 Wool Anatomy 0.000 claims description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 235000018553 tannin Nutrition 0.000 claims description 2
- 229920001864 tannin Polymers 0.000 claims description 2
- 239000001648 tannin Substances 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N Manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims 2
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 claims 2
- 208000006558 Dental Calculus Diseases 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000000095 emetic Effects 0.000 claims 1
- 239000002895 emetic Substances 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000010446 mirabilite Substances 0.000 claims 1
- 230000001376 precipitating Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 claims 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 3
- GUAWMXYQZKVRCW-UHFFFAOYSA-N N,2-dimethylaniline Chemical compound CNC1=CC=CC=C1C GUAWMXYQZKVRCW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229940095076 benzaldehyde Drugs 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Chemical class 0.000 description 2
- 239000011707 mineral Chemical class 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- MFHPYLFZSCSNST-UHFFFAOYSA-N 1-chloro-2-(trichloromethyl)benzene Chemical compound ClC1=CC=CC=C1C(Cl)(Cl)Cl MFHPYLFZSCSNST-UHFFFAOYSA-N 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N Diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 229940107698 Malachite green Drugs 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 239000001046 green dye Substances 0.000 description 1
- VFCNQNZNPKRXIT-UHFFFAOYSA-N malachite green cation Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 VFCNQNZNPKRXIT-UHFFFAOYSA-N 0.000 description 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M superoxide Chemical class [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 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
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
- C09B11/14—Preparation from aromatic aldehydes, aromatic carboxylic acids or derivatives thereof and aromatic amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMTPATENT OFFICE
Im Gegensatz zu Dimethylanilin und Diäthylanilin condensiren sich die Dialkylderivate des o-Toluidins unter den üblichen Bedingungen bekanntlich nicht mit den aromatischen Aldehyden. Dagegen liefern die Monoalkyl-otoluidine mit derselben Leichtigkeit Körper der Triphenylmethanreihe, wie das Dimethylanilin.In contrast to dimethylaniline and diethylaniline, the dialkyl derivatives of It is well known that o-toluidine does not react with the aromatic aldehydes under the usual conditions. In contrast, the monoalkyl otoluidines deliver bodies of the triphenylmethane series with the same ease as dimethylaniline.
Sie unterscheiden sich also hierdurch wesentlich von den Monoalkylanilinen, welche letzteren unter ähnlichen Bedingungen vorwiegend Anhydroverbindungen liefern und sich demnach dem Anilin analog verhalten.In this way they differ significantly from the monoalkylanilines, the latter under similar conditions predominantly deliver anhydro compounds and accordingly behave analogously to aniline.
Während Dimethylanilin mit Benzaldehyd einen grünen Farbstoff, das Malachitgrün, liefert, bringt das Monomethyl-o-toluidin mit Benzaldehyd und darauf folgender Oxydation einen grünblauen Farbstoff hervor, der allerdings wegen seiner stumpfen Nuance nur untergeordnetes Interesse beansprucht.While dimethylaniline and benzaldehyde create a green dye, malachite green, supplies, brings the monomethyl-o-toluidine with benzaldehyde and subsequent oxidation a green-blue dye emerges, but only because of its dull shade subordinate interest claimed.
Dagegen hat sich herausgestellt, dafs bei Verwendung des Dichlorbenzaldehydes. welcher von R. Gnehm, Ber. XVII, S. 752, zuerst beschrieben worden ist, und der auf verschiedenem Wege, ζ. B. nach der in der Patentschrift Nr. 32238 beschriebenen Methode aus Dichlorbenzylidenchlorid, dargestellt werden kann, sehr werthvolle blaue basische Farbstoffe von grofser Reinheit erhalten werden. Dieselben färben Wolle und Seide, sowie mit Tannin und Brechweinstein gebeizte Baumwolle blau, in der Nuance zwischen , dem blauesten Grün und dem bis jetzt bekannten grünsten Blau.In contrast, it has been found that when using dichlorobenzaldehyde. which by R. Gnehm, Ber. XVII, p. 752, and that on various Ways, ζ. B. by the method described in patent specification No. 32238 from dichlorobenzylidene chloride, very valuable blue basic dyes of great purity can be obtained. The same dye wool and silk, as well as cotton stained with tannin and tartarine blue, in the shade between, the bluest green and the greenest blue known up to now.
A. Condensation.A. Condensation.
Die Darstellung des symmetrischen Dimethyldiamido - ο - ditolyldichlorphenylmethans kann beispielsweise in der Art ausgeführt werden, dafs 60 Theile reines Monomethyl-o-toluidin mit 44 Theilen Dichlorbenzaldehyd, 60 Theilen Alkohol und 25 Theilen Schwefelsäure in einem mit Rührer versehenen und ausgebleiten Kessel während 24 Stunden im Wasserbade erwärmt werden.The representation of the symmetrical Dimethyldiamido - ο - ditolyldichlorphenylmethans can for example, be carried out in such a way that 60 parts of pure monomethyl-o-toluidine with 44 parts dichlorobenzaldehyde, 60 parts alcohol and 25 parts sulfuric acid in a kettle equipped with a stirrer and blown out in a water bath for 24 hours be heated.
Man übersättigt hierauf mit Natronlauge, treibt die eventuell unangegriffenen OeIe mit Wasserdampf ab und kocht die zurückbleibende Leukobase wiederholt mit Wasser aus.One then oversaturated with caustic soda, drives the possibly unaffected oils with it Steam and the remaining leuco base repeatedly boiled with water.
In analoger Weise erhält man das symmetrische Diäthyldiamido - ο - ditolyldichlorphenylmethan, wenn man statt Monomethyl-o-toluidin die entsprechende Menge Monoäthyl-o-toluidin anwendet.The symmetrical diethyldiamido - ο - ditolyldichlorophenylmethane is obtained in an analogous manner, if instead of monomethyl-o-toluidine the corresponding amount of monoethyl-o-toluidine applies.
An Stelle der Schwefelsäure kann zur Condensation Salzsäure oder Chlorzink verwendet werden.Instead of sulfuric acid, hydrochloric acid or zinc chloride can be used for condensation will.
Die nach diesem Verfahren erhaltenen Leukobasen sind in reinem Zustande farblose krystallinische Verbindungen, die sich leicht in Aether, Benzol, warmem Alkohol und Mineralsäuren auflösen, in Wasser und Alkalien dagegen unlöslich sind.The leuco bases obtained by this process are colorless in their pure state Crystalline compounds that are easily broken down into ether, benzene, warm alcohol, and mineral acids dissolve, but are insoluble in water and alkalis.
B. Oxydation.B. Oxidation.
Zur Ueberführung der Leukobasen in die Farbstoffe werden dieselben in verdünnten Mineralsä'uren gelöst und mit geeigneten Oxydationsmitteln, z. B. mit Superoxyden, oxydirt.To transfer the leuco bases to the The same dyes are dissolved in dilute mineral acids and treated with suitable oxidizing agents, z. B. with superoxides, oxidized.
Es werden z. B. 30 Theile symmetrisches Dimethyldiamido - ο - ditolyldichlorphenylmethan in 40 Theilen Salzsäure und 1500 Theilen Wasser gelöst und zu dieser Lösung die berechnete Menge in Wasser aufgeschlemmtesThere are z. B. 30 parts of symmetrical dimethyldiamido - ο - ditolyldichlorophenylmethane dissolved in 40 parts hydrochloric acid and 1500 parts water, and the calculated solution for this solution Amount of dissolved in water
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE71370C true DE71370C (en) |
Family
ID=344681
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT71370D Expired - Lifetime DE71370C (en) | Process for the preparation of blue basic dyes of the triphenylmethane series from dichlorobenzaldehyde |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE71370C (en) |
-
0
- DE DENDAT71370D patent/DE71370C/en not_active Expired - Lifetime
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