DE69199C - Procedure for representing a! Acid dye of the malachite green series - Google Patents
Procedure for representing a! Acid dye of the malachite green seriesInfo
- Publication number
- DE69199C DE69199C DENDAT69199D DE69199DA DE69199C DE 69199 C DE69199 C DE 69199C DE NDAT69199 D DENDAT69199 D DE NDAT69199D DE 69199D A DE69199D A DE 69199DA DE 69199 C DE69199 C DE 69199C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- representing
- procedure
- acid dye
- malachite green
- 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.)
- Active
Links
- 239000000980 acid dye Substances 0.000 title description 3
- VFCNQNZNPKRXIT-UHFFFAOYSA-N malachite green cation Chemical class C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 VFCNQNZNPKRXIT-UHFFFAOYSA-N 0.000 title 1
- 239000002253 acid Substances 0.000 claims description 13
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 4
- SLXZZXJPFRYIKN-UHFFFAOYSA-N benzyl-(2-ethylphenyl)sulfamic acid Chemical compound CCC1=CC=CC=C1N(S(O)(=O)=O)CC1=CC=CC=C1 SLXZZXJPFRYIKN-UHFFFAOYSA-N 0.000 claims description 2
- 150000003871 sulfonates Chemical class 0.000 claims 1
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 235000002639 sodium chloride Nutrition 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 3
- 235000015450 Tilia cordata Nutrition 0.000 description 3
- 235000011941 Tilia x europaea Nutrition 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000004571 lime Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- KEQXNNJHMWSZHK-UHFFFAOYSA-L 1,3,2,4$l^{2}-dioxathiaplumbetane 2,2-dioxide Chemical compound [Pb+2].[O-]S([O-])(=O)=O KEQXNNJHMWSZHK-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- -1 Zinc chlorine Chemical compound 0.000 description 2
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 239000001046 green dye Substances 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride 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
- 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
- C09B11/22—Amino derivatives of triarylmethanes containing OH groups bound to an aryl nucleus and their ethers and esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Durch Einwirkung von m - Oxybenzaldehyd auf Aethylbenzylanilinsulfosäüre in Gegenwart von Chlorzink entsteht eine Disulfosäure des Diäthyldibenzyldiamido-m-oxytriphenylmethans. Diese läfst sich leicht in eine Tetrasulfosäure überführen, welche bei der Oxydation einen alkaliechten blaugrünen Säurefarbstoff liefert. Derselbe Farbstoff wird auch in der Weise gewonnen, dafs man obengenannte m-Oxydiäthyldibenzyldiamidotriphenylmethandisulfosäure durch Oxydation in m-Oxydiäthyldibenzyldiamidotriphenylcarbinoldisulfosäure verwandelt und letztere durch weitere Sulfonirung in den blaugrünen alkaliechten Säurefarbstoff überführt. By the action of m-oxybenzaldehyde on Aethylbenzylanilinsulfosäüre in the presence Zinc chlorine produces a disulfonic acid of diethyldibenzyldiamido-m-oxytriphenylmethane. This can easily be converted into a tetrasulphonic acid, which causes one in the oxidation provides alkaline blue-green acid dye. The same dye is obtained in the same way that the abovementioned m-oxydiethyldibenzyldiamidotriphenylmethanedisulfonic acid is used by oxidation in m-oxydiäthyldibenzyldiamidotriphenylcarbinoldisulfonic acid and the latter is converted into the blue-green, alkaline-like acid dye by further sulphonation.
24 kg m-Oxybenzaldehyd, 116 kg Aethylbenzylanilinsulfosäüre, 120 kg Chlorzinklösung (1:1) (sogen. Zinksäure) werden ca. 2 Tage auf dem Wasserbad erwärmt.24 kg m-oxybenzaldehyde, 116 kg ethylbenzylaniline sulfonic acid, 120 kg of zinc chloride solution (1: 1) (so-called zinc acid) are stored for approx. 2 days warmed up in the water bath.
Zur Entfernung des Chlorzinks Wird mehrere Male mit Wasser ausgekocht, wobei sich die in Wasser schwer lösliche Sulfosäure als eine zähe Masse abscheidet, welche beim Erkalten fest wird und sich dann leicht pulvern läfst. Dieselbe wird bei ca. 300 getrocknet. Man erhält auf diese Weise ein sehr reines Product und eine gute Ausbeute.To remove the chlorine zinc it is boiled several times with water, whereby the sulphonic acid, which is sparingly soluble in water, separates out as a viscous mass, which solidifies when it cools and can then be easily powdered. The same is dried at about 30 0th A very pure product and a good yield are obtained in this way.
Die so erhaltene m - Oxydibenzyldiäthyldiamidotriphenylmethandisulfosäure wurde zur Ueberführung in eine Tetrasulfosäure wie folgt behandelt:The m-oxydibenzyl diethyldiamidotriphenylmethanedisulfonic acid thus obtained was treated as follows to convert it into a tetrasulfonic acid:
50 kg m-Oxydiäthyldibenzyldiamidotriphenylmethandisulfosäure werden in 250 kg rauchende Schwefelsäure von 20 pCt. S O3 unter gutem Umrühren eingetragen. Die Lösung wird einige Stunden auf γο° erwärmt, dann auf Eis gegossen und in bekannter Weise auf das Kalksalz verarbeitet.50 kg of m-oxydiäthyldibenzyldiamidotriphenylmethanedisulfonic acid are dissolved in 250 kg of fuming sulfuric acid of 20 pCt. S O 3 entered with thorough stirring. The solution is warmed to γο ° for a few hours, then poured onto ice and processed in the known manner on the lime salt.
Die Oxydation der m-Oxydibenzyldiäthyldiamidotriphenylmethantetrasulfosäure wird in folgender Weise ausgeführt:The oxidation of m-Oxydibenzyldiäthyldiamidotriphenylmethantetrasulfonic acid is carried out in the following way:
46 kg Kalksalz der Sulfosäure werden in Wasser gelöst, dann mit der berechneten Menge verdünnter Schwefelsäure und Bleisuperoxyd versetzt, vom abgeschiedenen Bleisulfat abfiltrirt und die blaue Farbstofflösung zur Trockene verdampft.46 kg of lime salt of sulfonic acid are dissolved in water, then with the calculated amount dilute sulfuric acid and lead peroxide are added, and the separated lead sulphate is filtered off and the blue dye solution evaporates to dryness.
Will man denselben Farbstoff darstellen durch Oxydation der m-Oxydiäthyldibenzyldiamidotriphenylmethandisulfosäure und darauffolgende Sulfonirung des entsprechenden Carbinols, so verfährt man wie folgt:If one wants to produce the same dye by oxidation of the m-oxydiäthyldibenzyldiamidotriphenylmethanedisulfonic acid and subsequent sulphonation of the corresponding carbinol, proceed as follows:
34 kg m-Oxydibenzyldiäthyldiamidotriphenylmethandisulfosäure werden mit der berechneten Menge Sodalösung neutralisirt, die berechnete Menge Bleisuperoxyd und verdünnte Schwefelsäure hinzugegeben, vom ausgeschiedenen Bleisulfat abfiltrirt und der Farbstoff mit Kochsalz ausgesalzen.34 kg of m-oxydibenzyl diethyldiamidotriphenylmethanedisulfonic acid are neutralized with the calculated amount of soda solution, the calculated Amount of lead peroxide and dilute sulfuric acid added, of the precipitated lead sulphate filtered off and the dye salted out with table salt.
Zur Sulfonirung dieses grünen Farbstoffes werden 5 kg m-Oxydibenzyldiäthyldiamidotriphenylcarbinolsulfosäure in .30 kg Schwefelsäuremonohydrat gelöst, dann auf 50 bis 6o° so lange erwärmt, bis eine Probe von verdünntem Ammoniak mit blauer Farbe gelöst5 kg of m-oxydibenzyl diethyldiamidotriphenylcarbinol sulfonic acid are used to sulfonate this green dye Dissolved in .30 kg of sulfuric acid monohydrate, then heated to 50 to 60 ° until a sample of dilute Ammonia dissolved with a blue color
wird. Das Reactionsproduct wird darauf in oben angegebener Weise auf Kalksalz verarbeitet. will. The reaction product is then processed on lime salt in the manner indicated above.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE69199C true DE69199C (en) |
Family
ID=342686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT69199D Active DE69199C (en) | Procedure for representing a! Acid dye of the malachite green series |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE69199C (en) |
-
0
- DE DENDAT69199D patent/DE69199C/en active Active
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