DE81376C - - Google Patents
Info
- Publication number
- DE81376C DE81376C DENDAT81376D DE81376DA DE81376C DE 81376 C DE81376 C DE 81376C DE NDAT81376 D DENDAT81376 D DE NDAT81376D DE 81376D A DE81376D A DE 81376DA DE 81376 C DE81376 C DE 81376C
- Authority
- DE
- Germany
- Prior art keywords
- phenylenediamine
- tolylenediamine
- diamines
- dyes
- pyrogallol
- 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
- WQGWDDDVZFFDIG-UHFFFAOYSA-N Pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 10
- 239000000975 dye Substances 0.000 claims description 8
- 229940079877 Pyrogallol Drugs 0.000 claims description 5
- FCWPLGWNMBKCKT-UHFFFAOYSA-N 4-diazocyclohexa-1,5-dien-1-ol Chemical class OC1=CCC(=[N+]=[N-])C=C1 FCWPLGWNMBKCKT-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- -1 methyl - Chemical class 0.000 claims description 3
- 239000000987 azo dye Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 2
- 238000004040 coloring Methods 0.000 claims 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N P-Phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-N,4-N-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 description 1
- OZCJSIBGTRKJGX-UHFFFAOYSA-N 4-methylcyclohexa-1,5-diene-1,4-diamine Chemical class CC1(N)CC=C(N)C=C1 OZCJSIBGTRKJGX-UHFFFAOYSA-N 0.000 description 1
- URFIVLCFWRDUFB-UHFFFAOYSA-N C(CC)C1(CC=C(C=C1)N)N Chemical compound C(CC)C1(CC=C(C=C1)N)N URFIVLCFWRDUFB-UHFFFAOYSA-N 0.000 description 1
- BZORFPDSXLZWJF-UHFFFAOYSA-N Dimethyl-4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 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
- 150000007513 acids Chemical class 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 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
- 239000002966 varnish 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/12—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group of the benzene series
-
- E—FIXED CONSTRUCTIONS
- E01—CONSTRUCTION OF ROADS, RAILWAYS, OR BRIDGES
- E01B—PERMANENT WAY; PERMANENT-WAY TOOLS; MACHINES FOR MAKING RAILWAYS OF ALL KINDS
- E01B9/00—Fastening rails on sleepers, or the like
- E01B9/02—Fastening rails, tie-plates, or chairs directly on sleepers or foundations; Means therefor
- E01B9/28—Fastening on wooden or concrete sleepers or on masonry with clamp members
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Mechanical Engineering (AREA)
- Architecture (AREA)
- Civil Engineering (AREA)
- Structural Engineering (AREA)
- Color Printing (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT. Y<SPATENT OFFICE. Y <S
Im Haupt-Patente ist gezeigt, dafs p-Diazophenole sich unerwarteter Weise mit Pyrogallol in alkalischer Lösung zu braunen, beizenfärbenden Azofarbstoffen verbinden.In the main patents it is shown that p-diazophenols unexpectedly combine with pyrogallol combine in an alkaline solution to form brown, stain-staining azo dyes.
Diese Eigenschaft der p-Diazophenole besitzen nun auch die p-Diazoamine, d. h. die Monodiazoderivate der ρ-Diamine. Offenbar gilt diese Reaction allgemein für diejenigen Diazoverbindungen, welche noch eine O H- oder NH2- Gruppe (be^zw. alkylirte NH2-Gruppe) in p-Stellung enthalten.The p-diazoamines, ie the monodiazo derivatives of the ρ-diamines, now also have this property of the p-diazophenols. Apparently, this reaction is general for those diazo compounds, which have a O H or NH 2 - (. ^ Zw be alkylirte NH 2 - group) group in the para position included.
Mittelst p-Phenylendiamins und p-Toluylendiamins erhält man Farbstoffe, welche die chromirte Faser braunviolett färben, während die substituirten Diamine, wie Dimethyl-ρ-phenylendiamin oder Diäthyl-p-phenylendiamin, Farbstoffe liefern, deren Chromlacke in hellen Nuancen grauviolett, in dunklen dagegen schwarzviolett bis tiefschwarz gefärbt sind. Methyl- und Aethyl-p-Toluylendiamin geben Farbstoffe von rötherer Nuance. Alle diese Farbstoffe sind dadurch gekennzeichnet, dafs sie mit Mineralsäuren leicht lösliche, bräunlichgelb gefärbte Salze bilden, welche auch mit Tanninbeizen braun bis grau gefärbte Lacke erzeugen; Alkalien liefern schwer lösliche, dunkelbraun gefärbte Salze.Middle p-phenylenediamines and p-tolylenediamines dyes are obtained which color the chromed fiber brownish-violet, while the substituted Diamines, such as dimethyl-ρ-phenylenediamine or diethyl-p-phenylenediamine, dyes deliver their chrome lacquers in light shades of gray-violet, in contrast to dark ones are black-violet to deep black in color. Give methyl- and ethyl-p-toluenediamine Dyes of a redder shade. All these dyes are characterized by the fact that they form easily soluble, brownish-yellow colored salts with mineral acids, which also with Tannin stains produce varnishes that are brown to gray in color; Alkalis provide poorly soluble, dark brown colored salts.
Auch Sulfosäuren der p-Diamine lassen sich verwenden; der Chromlack des Farbstoffes aus Aethylbenzyl - ρ - phenylendiaminsulfosäure und Pyrogallol giebt dunkelviolette Töne.Sulfonic acids of the p-diamines can also be used; the chrome lacquer of the dye Ethylbenzyl - ρ - phenylenediaminesulfonic acid and pyrogallol give dark purple tones.
I. 22 kg p-Phenylendiamin und 14 kg Nitrit werden in 300 1 Wasser gelöst und in ein Gemisch von 55 kg Salzsäure von'21 0B.' und 400 kg Eis unter gutem Rühren einfliefsen gelassen. Unter diesen Umständen bildet sich zum gröfsten Theile die Monodiazoverbindung des p-Phenylendiamins.I. 22 kg of p-phenylenediamine and 14 kg of nitrite are dissolved in 300 1 of water and in a mixture of 55 kg of hydrochloric acid of '21 0 B. ' and allowed to flow in 400 kg of ice with thorough stirring. Under these circumstances the monodiazo compound of p-phenylenediamine is for the most part formed.
Dazu wird eine Lösung von 26 kg Pyrogallol in 100 1 Wasser und nachher von 50 kg Soda in 180 1 Wasser gegeben; nach mehrstündigem Stehenlassen säuert man mit 100 kg Salzsäure an und filtrirt den Farbstoff ab, welcher am besten als Teig zur Verwendung gelangt.A solution of 26 kg of pyrogallol in 100 l of water and then 50 kg of soda is used given in 180 l of water; after several hours Leave to stand, acidify with 100 kg of hydrochloric acid and filter off the dye, which am is best used as a dough.
II. 13,5 kg Dimethyl-p-phenylendiamin und 7 kg Natriumnitrit werden in 100 1 Wasser gelöst und behufs Diazotirung in ein Gemisch von 25 kg Salzsäure von 210B. und 200 kg Eis unter gutem Rühren einfliefsen gelassen. Hierauf fügt man eine Lösung von 125 kg Pyrogallol in 30 1 Wasser und nachher unter gutem Rühren eine Lösung von 25 kg Soda in 80 1 Wasser hinzu. Nach mehrstündigem Stehenlassen wird durch Zusatz von 50 kg Salzsäure angesäuert und das ausgeschiedene Chlorhydrat des Farbstoffes abfiltrirt. DerselbeII. 13.5 kg dimethyl-p-phenylenediamine and 7 kg of sodium nitrite dissolved in 100 1 of water and behufs Diazotirung in a mixture of 25 kg of hydrochloric acid 21 0 B. and 200 kg of ice with good stirring left einfliefsen. A solution of 125 kg of pyrogallol in 30 l of water is then added, followed by a solution of 25 kg of soda in 80 l of water with thorough stirring. After standing for several hours, the mixture is acidified by adding 50 kg of hydrochloric acid and the precipitated hydrochloric acid of the dye is filtered off. Same
Claims (1)
Die Anwendung des unter 1. gekennzeichneten Verfahrens auf folgende p-Diamine: ρ - Phenylendiamin , ρ - Toluylendiamin, Dimethyl - ρ - phenylendiamin, Diäthyl - pphenylendiamin, Methyl - ρ - toluylendiamin, Aethyl - ρ - toluylendiamin, Aethylbenzyl-pphenylendiaminsulfosäure. Innovation in the process identified in Patent No. 81109 for the preparation of stain-coloring azo dyes made from pyrogallol, consisting in the fact that this is combined with the monodiazo compounds of the p-diamines in an alkaline solution instead of the p-diazophenols mentioned in the main patent.
The application of the procedure identified under 1. to the following p-diamines: ρ - phenylenediamine, ρ - tolylenediamine, dimethyl - ρ - phenylenediamine, diethyl - pphenylenediamine, methyl - ρ - tolylenediamine, ethyl - ρ - tolylenediamine, ethylbenzyl-pphenylenediaminesulfonic acid.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE81376C true DE81376C (en) |
Family
ID=353864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT81376D Active DE81376C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE81376C (en) |
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0
- DE DENDAT81376D patent/DE81376C/de active Active
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