DE80669C - - Google Patents
Info
- Publication number
- DE80669C DE80669C DENDAT80669D DE80669DA DE80669C DE 80669 C DE80669 C DE 80669C DE NDAT80669 D DENDAT80669 D DE NDAT80669D DE 80669D A DE80669D A DE 80669DA DE 80669 C DE80669 C DE 80669C
- Authority
- DE
- Germany
- Prior art keywords
- naphthylamine
- dyes
- ethoxyphenyl
- leuco
- resulting
- 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
- 239000000975 dye Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 3
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 3
- 150000004005 nitrosamines Chemical class 0.000 claims description 2
- GESUXCLRERRNSQ-UHFFFAOYSA-N 1-benzhydrylnaphthalene Chemical compound C1=CC=CC=C1C(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 GESUXCLRERRNSQ-UHFFFAOYSA-N 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- 241000974482 Aricia saepiolus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 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 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- VQYJLACQFYZHCO-UHFFFAOYSA-N hydron;4-methoxyaniline;chloride Chemical compound [Cl-].COC1=CC=C([NH3+])C=C1 VQYJLACQFYZHCO-UHFFFAOYSA-N 0.000 description 1
- JQKBUTDZZRGQDR-UHFFFAOYSA-N hydron;4-methylaniline;chloride Chemical compound Cl.CC1=CC=C(N)C=C1 JQKBUTDZZRGQDR-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin 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
- C09B11/16—Preparation from diarylketones or diarylcarbinols, e.g. benzhydrol
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
In der Patentschrift Nr. 66712 ist ein Verh bhi L llIn patent specification no. 66712 a Verh bhi L ll
fahren beschrieben, Leukobasen
gemeinen Typus:drive described, leuco bases
common type:
/ C1. H. — N Rn / C 1 . H. - NR n
vomfrom the
allge-general
HC-HC-
.R' _ NHR" C6H, -N R2 .R ' _ NHR "C 6 H, -NR 2
(in welchem Formelbild R aliphatische, R' aromatische und R" Radicale beliebiger Art darstellen) glatt durch Oxydation in Farbstoff überzuführen, indem man die Leukobasen in ihre Nitrosamine verwandelt, letztere der Oxydation unterwirft und darauf die Nitrosogruppe durch geeignete Mittel wieder abspaltet.(in which formula R represent aliphatic, R ' aromatic and R " radicals of any kind) can be converted smoothly into dye by oxidation by converting the leuco bases into their nitrosamines, subjecting the latter to oxidation and then splitting off the nitroso group again by suitable means.
Dieses Verfahren läfst sich mit Vortheil auch auf einige andere Leukobasen dieser Art ausdehnen, nämlich auf die Condensationsproducte aus den alkylirten Diamidobenzhydrolen und p-Methoxy- oder p-Aethoxyphenyl-a-naphtylamin, welche letztere Componenten durch Erhitzen von a-Naphtylamin mit salzsaurem p-Anisidin bezw. p-Phenetidin dargestellt werden.This procedure can also be used with advantage extend to some other leuco bases of this kind, namely, to the condensation products from the alkylated diamidobenzhydrols and p-methoxy- or p-ethoxyphenyl-a-naphthylamine, the latter components by heating a-naphthylamine with hydrochloric acid p-anisidine respectively p-phenetidine can be shown.
Das p-Methoxyphenyl-a-naphtylamin bildet farblose Blättchen vom Schmelzpunkt iio°.The p-methoxyphenyl-a-naphthylamine forms colorless leaflets with a melting point of 10 °.
Das p-Aethoxyphenyl-a-naphtylamin krystallisirt in glänzenden Prismen, welche bei 890 schmelzen.The p-ethoxyphenyl-a-naphthylamine crystallizes in shining prisms, which melt at 89 0th
Um die so erhaltenen Leukobasen in Farbstoffe überzuführen, verfährt man, wie im Haupt-Patent angegeben.In order to convert the leuco bases thus obtained into dyes, the procedure is as in Main patent stated.
49 kg der aus p-Methoxy-a-naphtylamin und Tetramethyldiamidobenzhydrol (oder die entsprechende Menge der aus p-Aethoxy-a-naphtylamin und Tetramethyldiamidobenzhydrol) dargestellten Leukobase werden in 160 kg Essigsäure von 30 pCt. unter Zusatz von 73 kg Salzsäure von 20 pCt. gelöst und unter Abkühlen mit 70 kg ι ο procentiger Nitritlösung in das Nitrosamin übergeführt. Zwecks Oxydation setzt man 160 kg Bleisuperoxydpaste (15 pCt. Gehalt an Pb O2) zu; nach einiger Zeit werden 14,7 kg salzsaures p-Toluidin, gelöst in 25 kg 20 procentiger Schwefelsäure, und schh'elslich allmä'lig 200 kg 36 procentiger Salzsäure in die gesammte Reactionsmasse eingerührt und so lange bei gewöhnlicher Temperatür stehen gelassen, bis eine herausgenommene Probe mit Wasser versetzt keine Aenderung der blauen Nuance zeigt. Hierauf wird vom Blei abfiltrirt und mit 8000 1 Wasser verdünnt, wobei sich der Farbstoff als braunes Pulver abscheidet und durch Absaugen von der Mutterlauge getrennt wird.49 kg of the leuco base prepared from p-methoxy-a-naphthylamine and tetramethyldiamidobenzhydrol (or the corresponding amount of the leuco base from p-ethoxy-a-naphthylamine and tetramethyldiamidobenzhydrol) are dissolved in 160 kg acetic acid of 30 pCt. with the addition of 73 kg hydrochloric acid of 20 pCt. dissolved and converted into the nitrosamine while cooling with 70 kg ι ο percent nitrite solution. For the purpose of oxidation, 160 kg of lead peroxide paste (15 pCt. Content of Pb O 2 ) are added; After a while, 14.7 kg of hydrochloric acid p-toluidine, dissolved in 25 kg of 20 percent sulfuric acid, and gradually 200 kg of 36 percent hydrochloric acid are stirred into the entire reaction mass and left to stand at the usual temperature until one is removed Sample mixed with water shows no change in the blue shade. The lead is then filtered off and diluted with 8,000 liters of water, the dye separating out as a brown powder and being separated from the mother liquor by suction.
Die Abspaltung der Nitrosogruppe kann auch durch andere im Haupt - Patent erwähnte, Salpetrigsäure bindende Mittel (schweflige Säure etc.) bewirkt werden.The cleavage of the nitroso group can also be carried out by others mentioned in the main patent, Nitrous acid binding agents (sulphurous acid etc.) can be effected.
Der Farbstoff färbt Wolle und mit Tannin gebeizte Baumwolle in äufserst klaren grünblauen Nuancen an. The dye stains wool and tannin-stained cotton in extremely clear green-blue shades.
In ganz analoger Weise werden die Färb-In a completely analogous way, the coloring
Stoffe aus der Leukobase von tetraäthylirtem Amidobenzhydrol und ρ - Aethoxyphenyl - anaphtylamin gewonnen. Die Farbstoffe aus Tetramethyldiamidobenzhydrol und p-Methoxyphenyl-a-naphtylamin bezw. p-Aethoxyphenyl-a-naphtylamin sind braune Pulver, welche sich in heifsem Wasser leicht mit grünlich blauer Farbe lösen und grünlich blaue Färbungen liefern.Substances obtained from the leuco base of tetraethylated amidobenzhydrol and ρ - ethoxyphenyl - a naphthylamine. The dyes from tetramethyldiamidobenzhydrol and p-methoxyphenyl-a-naphthylamine respectively. p-Ethoxyphenyl-a-naphthylamine are brown powders, which easily dissolve in hot water with a greenish-blue color and give a greenish-blue coloration.
Die aus Tetraä'thyldiamidobenzhydrol und den genannten Basen entstehenden Farbstoffe unterscheiden sich von vorgenannten nur durch eine etwas gröfsere Löslichkeit und grünstichigere Nuance.The dyes formed from Tetraethyldiamidobenzhydrol and the bases mentioned differ from the above only in their somewhat greater solubility and a more greenish tinge Nuance.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE80669C true DE80669C (en) |
Family
ID=353202
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT80669D Active DE80669C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE80669C (en) |
-
0
- DE DENDAT80669D patent/DE80669C/de active Active
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