DE6714C - Process for the preparation of the sulfonic acids from the green dyes, which are formed by the action of benzotrichloride or chlorinated benzotrichlorides on aromatic tertiary amines in the presence of metal chlorides. - Google Patents
Process for the preparation of the sulfonic acids from the green dyes, which are formed by the action of benzotrichloride or chlorinated benzotrichlorides on aromatic tertiary amines in the presence of metal chlorides.Info
- Publication number
- DE6714C DE6714C DENDAT6714D DE6714DA DE6714C DE 6714 C DE6714 C DE 6714C DE NDAT6714 D DENDAT6714 D DE NDAT6714D DE 6714D A DE6714D A DE 6714DA DE 6714 C DE6714 C DE 6714C
- Authority
- DE
- Germany
- Prior art keywords
- benzotrichlorides
- benzotrichloride
- chlorinated
- sulfonic acids
- tertiary amines
- 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
- XEMRAKSQROQPBR-UHFFFAOYSA-N Benzotrichloride Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 title claims description 8
- 239000001046 green dye Substances 0.000 title claims description 5
- 150000003460 sulfonic acids Chemical class 0.000 title claims description 5
- -1 aromatic tertiary amines Chemical class 0.000 title claims description 4
- 229910001510 metal chloride Inorganic materials 0.000 title claims description 4
- 238000000034 method Methods 0.000 title description 2
- 238000002360 preparation method Methods 0.000 title description 2
- 150000003839 salts Chemical class 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000875 corresponding Effects 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L Calcium hydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- FDZZZRQASAIRJF-UHFFFAOYSA-M Malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 description 1
- 229940107698 Malachite green Drugs 0.000 description 1
- DYFFAVRFJWYYQO-UHFFFAOYSA-N N-methyl-N-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- 235000015450 Tilia cordata Nutrition 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 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
- XOSXWYQMOYSSKB-UHFFFAOYSA-L water blue Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=C(N)C(C)=CC(C(=C2C=CC(C=C2)=NC=2C=CC(=CC=2)S([O-])(=O)=O)C=2C=CC(NC=3C=CC(=CC=3)S(O)(=O)=O)=CC=2)=C1 XOSXWYQMOYSSKB-UHFFFAOYSA-L 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
- C09B11/20—Preparation from other triarylmethane derivatives, e.g. by substitution, by replacement of substituents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
1878.1878.
ACTIEN-GESELLSCHAFT für ANILIN-FABRIKATION in BERLIN.ACTIEN-GESELLSCHAFT for ANILIN-FABRIKATION in BERLIN.
Verfahren zur Darstellung der Sulfosäuren aus den grünen Farbstoffen, welche durch Einwirkung von Benzotrichlorid oder gechlorten Benzotrichloriden auf aromatische tertiäre Amine bei Gegenwart von Metallchloriden gebildet werden.Process for the preparation of the sulfonic acids from the green dyes, which by the action of benzotrichloride or chlorinated benzotrichlorides on aromatic tertiary Amines are formed in the presence of metal chlorides.
Patentirt im Deutschen Reiche vom 27. October 1878 ab.Patented in the German Empire on October 27, 1878.
Die grünen Farbstoffe, welche durch Einwirkung von Benzotrichlorid oder gechlorten Benzotrichloriden auf aromatische tertiäre Amine bei Gegenwart von Metallchloriden gebildet werden, und von denen wir die aus Bimethylanilin und aus Methyldiphenylamin entstehenden gegenwärtig unter dem Namen »Malachitgrün« in den Handel bringen, bestehen im wesentlichen aus dem Zinkdoppelsalz einer farblosen Base, deren neutrale Salze grüne Lösungen bilden, während die sauren Salze gelb gefärbt sind. Werden die Basen dieser grünen Farbstoffe oder deren entsprechende Salze, z. B. Chloride oder Sulfate, mit einem Ueberschufs von concentrirter Schwefelsäure erwärmt, so bilden sich gepaarte Sulfosäuren, welche in ihrem Verhalten den Sulfosäuren des Anilinblau gleichen und wie diese in der Färberei und Druckerei angewendet werden können.The green dyes produced by the action of benzotrichloride or chlorinated benzotrichlorides on aromatic tertiary amines are formed in the presence of metal chlorides, and of which we presently those arising from bimethylaniline and from methyldiphenylamine Marketed under the name »Malachite Green« consist essentially of the zinc double salt of a colorless base, the neutral salts of which form green solutions, while the acid salts are colored yellow. Will the bases of these green dyes or their corresponding salts, e.g. B. chlorides or sulphates, with an excess of more concentrated When sulfuric acid is heated, paired sulfonic acids are formed, which behave differently Sulphonic acids of aniline blue are the same and, like these, are used in dyeing and printing can be.
Zur Erläuterung der fabrikmäfsigen Darstellung dieser Sulfosäuren erwähnen wir folgendes Beispiel:We mention the following in order to explain the production of these sulfonic acids Example:
Man nimmt zehn Theile der bei ioo° getrockneten Base oder einer äquivalenten Menge eines Salzes derselben, z. B. Chlorid, und trägt dieses unter beständigem Umrühren in neunzig Theile concentrirter Schwefelsäure Oder in die entsprechende Menge rauchender Schwefelsäure ein. Sobald sich der Farbstoff vollständig in der Säure gelöst hat, erwärmt man die Masse, bis eine gezogene Probe mit Alkalien keinen Niederschlag mehr giebt; nach dem Erkalten giefst man dann das Ganze in einen Ueberschufs von kaltem Wasser. Diese Lösung, die man mit Kalkmilch neutralisirt, wird zum Kochen erhitzt und der abgeschiedene Gyps durch Filtration getrennt.Ten parts are taken of those dried at 100 ° Base or an equivalent amount of a salt thereof, e.g. B. chloride, and carries this, with constant stirring, into ninety parts of concentrated sulfuric acid or into the corresponding amount of fuming sulfuric acid. Once the dye is completely in the acid has dissolved, the mass is heated until a sample is drawn with no alkalis Gives more precipitation; after cooling down, the whole thing is poured into an excess of cold water. This solution, which is neutralized with milk of lime, is brought to the boil heated and the deposited gypsum separated by filtration.
Aus der klaren Lösung setzt sich beim Erkalten ein Theil des Kalksalzes in farblosen krystallisirenden Krusten ab; der Rest wird durch Eindampfen der Lösung gewonnen.When the clear solution cools, part of the calcium salt turns colorless crystallizing crusts; the remainder is obtained by evaporating the solution.
Das so bereitete Kalksalz löst sich leicht in kochendem Wasser auf, färbt sich auf Zusatz von schwachen mineralischen oder organischen Säuren intensiv grün und kann sofort für die Zwecke der Färberei und Druckerei Verwendung finden.The lime salt prepared in this way dissolves easily in boiling water, changes color when added from weak mineral or organic acids intensely green and can be used immediately Purposes of dyeing and printing use.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE6714C true DE6714C (en) |
Family
ID=284789
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT6714D Active DE6714C (en) | Process for the preparation of the sulfonic acids from the green dyes, which are formed by the action of benzotrichloride or chlorinated benzotrichlorides on aromatic tertiary amines in the presence of metal chlorides. |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE6714C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3123473A (en) * | 1960-07-14 | 1964-03-03 | Photosensitive tgiphenyl methane |
-
0
- DE DENDAT6714D patent/DE6714C/en active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3123473A (en) * | 1960-07-14 | 1964-03-03 | Photosensitive tgiphenyl methane |
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