DE27948C - Process for the preparation of dyes by the action of the anhydrides of organic acids on the halogen salts of primary, secondary and tertiary aromatic amines - Google Patents
Process for the preparation of dyes by the action of the anhydrides of organic acids on the halogen salts of primary, secondary and tertiary aromatic aminesInfo
- Publication number
- DE27948C DE27948C DENDAT27948D DE27948DA DE27948C DE 27948 C DE27948 C DE 27948C DE NDAT27948 D DENDAT27948 D DE NDAT27948D DE 27948D A DE27948D A DE 27948DA DE 27948 C DE27948 C DE 27948C
- Authority
- DE
- Germany
- Prior art keywords
- water
- soluble
- dye
- dyes
- anhydrides
- 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
- 150000008064 anhydrides Chemical class 0.000 title claims description 15
- 239000000975 dye Substances 0.000 title claims description 14
- 239000011780 sodium chloride Substances 0.000 title claims description 12
- -1 halogen salts Chemical class 0.000 title claims description 11
- 229910052736 halogen Inorganic materials 0.000 title claims description 9
- 235000005985 organic acids Nutrition 0.000 title claims description 4
- 150000007524 organic acids Chemical class 0.000 title claims description 3
- 150000003336 secondary aromatic amines Chemical class 0.000 title claims description 3
- 150000003513 tertiary aromatic amines Chemical class 0.000 title claims description 3
- 238000000034 method Methods 0.000 title description 4
- 150000003142 primary aromatic amines Chemical class 0.000 title description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000001043 yellow dye Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- AJDUTMFFZHIJEM-UHFFFAOYSA-N N-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 10
- 235000002639 sodium chloride Nutrition 0.000 description 10
- 239000002585 base Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000001046 green dye Substances 0.000 description 8
- 150000004992 toluidines Chemical class 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000000446 fuel Substances 0.000 description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N Diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- WZCQRUWWHSTZEM-UHFFFAOYSA-N M-Phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical class 0.000 description 4
- 239000001049 brown dye Substances 0.000 description 4
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N Diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000001045 blue dye Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- MMCPOSDMTGQNKG-UHFFFAOYSA-N Anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-Methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- ITMSSZATZARZCA-UHFFFAOYSA-N N-ethyl-N-phenylaniline Chemical compound C=1C=CC=CC=1N(CC)C1=CC=CC=C1 ITMSSZATZARZCA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 description 2
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-Diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-Nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 description 1
- FZERHIULMFGESH-UHFFFAOYSA-N Acetanilide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- SEACYXSIPDVVMV-UHFFFAOYSA-L Eosin Y Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N Propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- QWDZADMNIUIMTC-UHFFFAOYSA-N Uranyl nitrate Chemical compound [O-][N+](=O)O[U-2](=O)(=O)O[N+]([O-])=O QWDZADMNIUIMTC-UHFFFAOYSA-N 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- BVQHHUQLZPXYAQ-UHFFFAOYSA-N acetyl butanoate Chemical compound CCCC(=O)OC(C)=O BVQHHUQLZPXYAQ-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating Effects 0.000 description 1
- 239000003638 reducing agent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 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
- C09B11/12—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)
- Cosmetics (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Dieses Verfahren betrifft die Darstellung von Farbstoffen durch Einwirkung der Anhydride organischer Säuren auf die Halogensalze primärer, secundärer und tertiärer aromatischer Amine in geschlossenen Gefäfsen mit oder ohne Anwendung von Condensationsmitteln.This method concerns the representation of dyes through the action of the anhydrides organic acids to the halogen salts of primary, secondary and tertiary aromatic Amines in closed vessels with or without the use of condensation agents.
Neu ist die Bildung der Farbstoffe durch Erhitzen der Halogensalze aromatischer Basen mit den Anhydriden organischer Säuren selbst ohne Anwendung von Condensationsmitteln, wie Zn Cl2, Al2 Cle etc. auf Temperaturen, die 2000C. nicht übersteigen.What is new is the formation of the dyes by heating the halogen salts of aromatic bases with the anhydrides of organic acids even without the use of condensation agents such as Zn Cl 2 , Al 2 Cl e etc. to temperatures which do not exceed 200 ° C.
Erhitzt man wasserfreies, salzsaures Anilin mit dem ι Y2 fachen bis doppelten Gewicht Essigsäureanhydrid in geschlossenem Gefäfs 12 Stunden auf eine Temperatur von 150 bis 2oo° C, so erhält man eine dickflüssige, braungelbe Schmelze, die eine grüngelbe Fluorescenz zeigt. Diese Schmelze scheidet, in Wasser gegossen, ein bräunlichgelbes Harz ab, das sich nicht in heifsem Wasser, dagegen leicht in verdünnter Salzsäure löst. Erhitzt man dieses Harz mit verdünnter Natronlauge, so erhält man kein Anilin, ein Beweis, dafs kein Acetanilid in der Schmelze gebildet wird. Die durch Kochen mit Natronlauge erhaltene, dunkelbraun aussehende Base giebt jedoch mit Salzsäure wieder das ursprüngliche, in Wasser unlösliche, Salz. Kocht man dagegen das Harz längere Zeit mit verdünnter Schwefelsäure, so entweicht Essigsäure und die durch überschüssiges Natron gefällte Base giebt jetzt mit Salzsäure ein in Wasser sehr leicht lösliches, in concentrirter Salzsäure farblos werdendes gelb gefärbtes Salz.If aniline, hydrochloric acid aniline is heated in a closed vessel to a temperature of 150 to 200 ° C for 12 hours with the ι Y 2 times to double the weight of acetic anhydride, a thick, brown-yellow melt is obtained, which shows a green-yellow fluorescence. When poured into water, this melt separates a brownish-yellow resin that does not dissolve in hot water, but dissolves easily in dilute hydrochloric acid. If this resin is heated with dilute sodium hydroxide solution, no aniline is obtained, which is proof that no acetanilide is formed in the melt. The base, obtained by boiling with sodium hydroxide solution, which looks dark brown, gives the original water-insoluble salt with hydrochloric acid. If, on the other hand, the resin is boiled for a long time with dilute sulfuric acid, acetic acid escapes, and the base precipitated by excess soda now gives, with hydrochloric acid, a yellow salt which is very easily soluble in water and becomes colorless in concentrated hydrochloric acid.
Es bildet sich also bei meinem Verfahren das salzsaure Acetylderivat eines gelben Farbstoffes, welches sich leicht durch Kochen mit verdünnter Schwefelsäure in den Farbstoff verwandeln läfst. Durch gleichzeitige Anwendung von Condensationsmitteln, wie z. B. völlig wasserfreies Zinkchlorid, Aluminiumchlorid etc., wird zwar die Einwirkung etwas beschleunigt, jedoch ist diese Anwendung nicht erforderlich. Durch Ersetzen des Anilins durch andere aromatische Basen, wie z. B. Tolüidin, Xylidin, Naphtylamin etc., werden Farbstoffe von sehr verschiedenen Nuancen erhalten. Sodann können die chlorwasserstoffsauren Salze durch die entsprechenden brom- oder jodwasserstoffsauren Salze ersetzt werden.So in my process the hydrochloric acid acetyl derivative of a yellow dye is formed, which can easily be converted into the dye by boiling with dilute sulfuric acid running. By simultaneous use of condensation agents, such as. B. completely anhydrous zinc chloride, aluminum chloride etc., the action is accelerated somewhat, however, this application is not required. By replacing the aniline with other aromatic ones Bases such as B. toluidine, xylidine, naphthylamine, etc., are dyes of very obtained different nuances. The hydrochloric acid salts can then be replaced by the corresponding bromo- or hydroiodic acid salts are replaced.
In diesem Verfahren kann ferner das Acetanhydrid durch seine Homologen, wie z. B. Valeriansäureanhydrid, sowie durch die gemischten Anhydride der Fettsäurereihe, wie z. B. Propionacetanhydrid, ersetzt werden. Ebenso können die Anhydride der aromatischen Reihe, sowie die gemischten Anhydride dieser und diejenigen, bestehend aus den Säureresten aromatischer und der Fettsäuren, wie z. B. Acetbenzoesäureanhydrid, angewendet werden.In this process, the acetic anhydride can also by its homologues, such as. B. Valeric anhydride, as well as the mixed anhydrides of the fatty acid series, such as. B. Propionic anhydride. Likewise, the anhydrides of the aromatic series, as well as the mixed anhydrides of these and those consisting of the acid residues more aromatic and the fatty acids, such as. B. Acetbenzoic anhydride, can be used.
Ein Beispiel erläutert die Darstellung der Farbstoffe.An example explains the representation of the dyes.
Z. B. Farbstoff aus salzsaurem Anilin: 12 kg salzsaures Anilin werden in einem geeigneten Autoklaven mit 18 kg Essigsäureanhydrid 12 Stunden auf 180 bis 2000 C. erhitzt.For example, dye made from hydrochloric aniline: 12 kg of hydrochloric aniline are heated to 180 to 200 ° C. for 12 hours with 18 kg of acetic anhydride in a suitable autoclave.
Die auf diese Weise erhaltene Schmelze wird alsdann in die fünffache Menge Wasser ge-The melt obtained in this way is then poured into five times the amount of water.
gössen. Hierbei scheidet sich der Farbstoff gröfstentheils als ein rothgelbes Harz ab, während die Mutterlauge noch etwas Farbstoff und noch etwas unangegriffenes Anilinsalz enthält. Das abgeschiedene Harz wird nun in geeigneter Retorte so lange mit der fünffachen Menge Wasser, das 20 bis 30 pCt. Schwefelsäure enthält, gekocht, bis sich im Destillate keine Essigsäure mehr findet. Alsdann wird die Lösung erkalten gelassen, filtrirt und schliefslich mit Soda oder Natronlauge übersättigt. Die gefällte Base wird mit wenig Salzsäure und Wasser gelöst, der Farbstoff durch Fällen mit Kochsalz und durch Umlösen in schwach kochsalzhaltigem Wasser zuletzt rein erhalten. Er bildet in gepulvertem Zustande ein dem Jaune d'or ähnlich sehendes gelbes Pulver und färbt Seide, Wolle und Baumwolle prachtvoll grüngelb.pour. Here the dye is for the most part deposited as a red-yellow resin, while the mother liquor still contains some dye and some unaffected aniline salt. The separated resin is now in a suitable retort with five times the amount Water containing 20 to 30 pCt. Contains sulfuric acid, cooked until there is none in the distillate Acetic acid finds more. The solution is then allowed to cool, filtered, and finally oversaturated with soda or caustic soda. The precipitated base is with a little hydrochloric acid and Dissolved water, the dye by precipitating with common salt and by dissolving in a weakly saline solution Ultimately, the water is kept pure. When powdered, it forms a yellow powder similar to the Jaune d'or and dyes silk, wool and cotton a splendid green-yellow.
Der Mechanismus der Reaction bei diesem Verfahren ist bei den Anhydriden der Fettreihe einfach der, dafs 2 Molecule des salzsauren Salzes der Base auf 1 Molecül des Anhydrides unter Abspaltung von 3 Molecülen Wasser einwirken, wodurch dann der Farbstoff gebildet wird. Etwas anders verläuft der Procefs bei den aromatischen Anhydriden. Hier wirken 2 Molecule des saksauren Salzes der Base auf 1 Molecül Anhydrid derart ein, dafs nur ι Molecül Wasser gebildet wird und 1 Molecül des Hydrates des angewendeten Anhydrides entsteht und sich dann ein Triphenylmethanderivat oder ein Homologes desselben bildet. Folgende Gleichungen erklären den Procefs:The mechanism of the reaction in this process is with the anhydrides of the fatty series simply that 2 molecules of the hydrochloric acid salt of the base to 1 molecule of the anhydride act with splitting off of 3 molecules of water, whereby the dye is then formed. It works a little differently Procefs with the aromatic anhydrides. Here are 2 molecules of the acidic salt of the Base to 1 molecule of anhydride in such a way that only 1 molecule of water is formed and 1 molecule the hydrate of the anhydride used is formed and then a triphenylmethane derivative is formed or forms a homologue thereof. The following equations explain the Procefs:
1) 2 Q H5 NH2 .HC/+ £j| £g>O = C11 H16 N2. 2 HC/+ 3 H2 O 1) 2 QH 5 NH 2 .HC / + £ j | £ g> O = C 11 H 16 N 2 . 2 HC / + 3 H 2 O
,\ 0 η WNH., \ 0 η WNH.
2) 2 C6H5 jv±/2.2) 2 C 6 H 5 jv ± / 2 .
= C19 H12-NH2 .2 HCl = C 19 H 12 -NH 2 .2 HCl
„ „/CO2H+ H2O "" / CO 2 H + H 2 O
c6 #*^jvO c 6 # * ^ jv O
Die nachbenannten Säure - Anhydride und Basen kommen zur Anwendung:The following acids - anhydrides and bases are used:
I. Anhydride.I. Anhydrides.
1. Essigsäureanhydrid,1. acetic anhydride,
2. Buttersäureanhydrid,2. butyric anhydride,
3. Essigsäurebuttersäureanhydrid, ,3. acetic acid butyric anhydride,
4. Benzoesäureanhydrid,4. benzoic anhydride,
5. Paranitrobenzoesäureanhydrid.5. Paranitrobenzoic anhydride.
II. Basen,
ι. Anilin,II. Bases,
ι. Aniline,
2. Toluidin,2. toluidine,
3. Xylidin,3. xylidine,
4. Diphenylamin,4. Diphenylamine,
5. Monomethylamin!,5. Monomethylamine !,
6. Monoäthy!anilin,6. Monoethy! Aniline,
7. Dimethylanilin,7. dimethylaniline,
8. Diäthylanilin,8. diethylaniline,
9. Metaphenylendiamin,
10. Metatoluylendiamin.9. metaphenylenediamine;
10. Metatolylenediamine.
Mit den oben genannten Säure-Anhydriden haben sich folgende Combmationen als technisch werthvoll erwiesen.With the acid anhydrides mentioned above, the following combinations have proven to be technical proven valuable.
A. Farbstoffe aus Acetanhydrid durch Einwirkung der Halogensalze von:A. Dyes from acetic anhydride due to the action of the halogen salts of:
1. Anilin, gelber Farbstoff (wasserlöslich),1. Aniline, yellow dye (soluble in water),
2. Toluidin (Para-, Ortho-), gelber Farbstoff (wasserlöslich),2. Toluidine (Para-, Ortho-), yellow dye (water-soluble),
3. Xylidin (Para-, Meta-, Ortho-), gelber Farbstoff (wasserlöslich),3. Xylidine (Para-, Meta-, Ortho-), yellow dye (water-soluble),
4. Metaphenylendiamin, braungelber Farbstoff (wasserlöslich),4. Metaphenylenediamine, brown-yellow dye (water-soluble),
5. Metatoluylendiamin,brauner Farbstoff (wasserlöslich), 5. Metatoluylenediamine, brown dye (water soluble),
6. Diphenylamin, gelber Farbstoff (spritlöslich).6. Diphenylamine, yellow dye (soluble in fuel).
B. Farbstoffe aus Buttersäureanhydrid, durch Einwirkung der Halogensalze von:B. dyes from butyric anhydride, by the action of the halogen salts of:
1. Anilin, orangegelber Farbstoff (wasserlöslich), 1. Aniline, orange-yellow dye (soluble in water),
2. Toluidin (Ortho-, Para-), orangegelber Farbstoff (wasserlöslich),2. Toluidine (ortho-, para), orange-yellow dye (water-soluble),
3. Xylidin (Ortho-, Para-, Meta-), orangegelber Farbstoff (wasserlöslich),3. Xylidine (ortho-, para-, meta-), orange-yellow dye (water-soluble),
4. Metaphenylendiamin, brauner Farbstoff (wasserlöslich),4. Metaphenylenediamine, brown dye (water soluble),
5. Metatoluylendiamin, brauner Farbstoff (wasserlöslich),5. Metatoluylenediamine, brown dye (water soluble),
6. Diphenylamin, gelber Farbstoff (spritlöslich).6. Diphenylamine, yellow dye (soluble in fuel).
C. Farbstoffe aus Acetbuttersäure-C. Colorants from Acetbutyric Acid
anhydrid
durch Einwirkung der Halogensalze von:anhydride
by the action of the halogen salts of:
1. Anilin, gelber Farbstoff (wasserlöslich),1. Aniline, yellow dye (soluble in water),
2. Toluidin (Ortho-, Para-), gelber Farbstoff (wasserlöslich),2. Toluidine (ortho-, para), yellow dye (water-soluble),
3. Xylidin (Ortho-, Para-, Meta-), gelber Farbstoff (wasserlöslich),3. Xylidine (ortho-, para-, meta-), yellow dye (water-soluble),
4. Metaphenylendiamin, braungelber Farbstoff (wasserlöslich),4. Metaphenylenediamine, brown-yellow dye (water-soluble),
5. Metatoluylendiamin,brauner Farbstoff (wasserlöslich), 5. Metatoluylenediamine, brown dye (water soluble),
6. Diphenylamin, gelber Farbstoff (spritlöslich).6. Diphenylamine, yellow dye (soluble in fuel).
D. Farbstoffe aus Benzoesäureanhydrid durch Einwirkung der Halogensalze von:D. Dyes from benzoic anhydride due to the action of the halogen salts of:
ι. Anilin, röthlich-blauer Farbstoff (wasserlöslich), ι. Aniline, reddish-blue dye (water-soluble),
2. Toluidin (Ortho-), röthlich-blauer Farbstoff (wasserlöslich),2. Toluidine (ortho-), reddish-blue dye (water-soluble),
3. Xylidin (Para-, Meta-), röthlich-blauer Farbstoff (wasserlöslich),3. Xylidine (Para-, Meta-), reddish-blue dye (water soluble),
4. Diphenylamin, grüner Farbstoff (spritlöslich),4. Diphenylamine, green dye (soluble in fuel),
5. Methylanilin, grüner Farbstoff (wasserlöslich),5. methyl aniline, green dye (water soluble),
6. Aethylanilin, grüner Farbstoff (wasserlöslich),6. Ethylaniline, green dye (water-soluble),
7. Dimethylanilin, grüner Farbstoff (wasserlöslich), 7. Dimethylaniline, green dye (water soluble),
8. Diäthylanilin, grünerFarbstoff(wasserlöslich),8. Diethylaniline, green dye (water soluble),
9. Methyldiphenylamin, grüner Farbstoff (spritlöslich), 9.Methyldiphenylamine, green dye (soluble in fuel),
10. Aethyldiphenylamin, grüner Farbstoff (spritlöslich). 10. Ethyldiphenylamine, green dye (soluble in fuel).
E. Farbstoffe aus Paranitrobenzoesäure-E. Paranitrobenzoic acid dyes
anhydrid
durch Einwirkung der Halogensalze von:anhydride
by the action of the halogen salts of:
1. Anilin, Paranitrodiamidotriphenylcarbinol,1. aniline, paranitrodiamidotriphenylcarbinol,
2. Toluidin, Paranitrodiamidoditolylphenylcarbinol, 2. toluidine, paranitrodiamidoditolylphenylcarbinol,
3. Xylidin, Paranitrodiamidodixylylphenylcarbinol, 3. xylidine, paranitrodiamidodixylylphenylcarbinol,
4. Diphenylamm, Paranitrodiamidopentaphenylcarbinol, 4. Diphenylamm, Paranitrodiamidopentaphenylcarbinol,
5. Methylanilin, Paranitrodiamidodimethyltriphenylcarbinol, 5. methylaniline, paranitrodiamidodimethyltriphenylcarbinol,
6. Aethylanilin, Paranitrodiamidodiäthyltriphenylcarbinol, 6. ethylaniline, paranitrodiamidodiethyltriphenylcarbinol,
7. Dimethylanilin, Paranitrodiamidötetramethyltriphenylcarbinol, 7. Dimethylaniline, Paranitrodiamidötetramethyltriphenylcarbinol,
8. Diäthylanilin, Paranitrodiamidotetraäthyltriphenylcarbinol, 8. Diethylaniline, Paranitrodiamidotetraäthyltriphenylcarbinol,
9. Methyldiphenylamin, Paranitrodiamidodimethylpentaphenylcarbinol, 9. methyldiphenylamine, paranitrodiamidodimethylpentaphenylcarbinol,
10. Aethyldiphenylamin, Paranitrodiamidodiäthylpentaphenylcarbinol. 10. Ethyldiphenylamine, paranitrodiamidodiethylpentaphenylcarbinol.
Die Körper dieser letzten Reihe sind sämmtlich spritlösliche grüne Farbstoffe, die jedoch nur dadurch werthvoll sind, dafs sie sich leicht durch geeignete Reductions- und Oxydationsmittel in die entsprechenden Rosaniline überführen lassen.The bodies in this last row are all gas-soluble green dyes, but they are are valuable only in that they are easily removed by suitable reducing and oxidizing agents can be converted into the corresponding rosanilines.
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