DE197035C - - Google Patents
Info
- Publication number
- DE197035C DE197035C DE1907197035D DE197035DA DE197035C DE 197035 C DE197035 C DE 197035C DE 1907197035 D DE1907197035 D DE 1907197035D DE 197035D A DE197035D A DE 197035DA DE 197035 C DE197035 C DE 197035C
- Authority
- DE
- Germany
- Prior art keywords
- dye
- amino
- water
- acid
- hydrochloric acid
- 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.)
- Expired - Lifetime
Links
- 239000000975 dye Substances 0.000 claims description 11
- HLVXFWDLRHCZEI-UHFFFAOYSA-N Chromotropic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 HLVXFWDLRHCZEI-UHFFFAOYSA-N 0.000 claims description 4
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 239000002253 acid Substances 0.000 description 3
- -1 nitroazo Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QRVRYKNKKHLWBW-UHFFFAOYSA-N 2-chloro-4-N,4-N-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C(Cl)=C1 QRVRYKNKKHLWBW-UHFFFAOYSA-N 0.000 description 2
- MRMXXMCXBZUJIW-UHFFFAOYSA-N 2-chloro-4-N,4-N-dimethylbenzene-1,4-diamine Chemical group CN(C)C1=CC=C(N)C(Cl)=C1 MRMXXMCXBZUJIW-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 210000002268 Wool Anatomy 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000001808 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 1
- 229940100198 ALKYLATING AGENTS Drugs 0.000 description 1
- BZORFPDSXLZWJF-UHFFFAOYSA-N Dimethyl-4-phenylenediamine Chemical class CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N Sodium sulfide Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M Tetraethylammonium bromide Chemical group [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- UPKAWFACSJWKND-ZXFFUEEESA-J tetrasodium;(6E)-4-amino-6-[[4-[4-[(2Z)-2-(8-amino-1-oxo-5,7-disulfonatonaphthalen-2-ylidene)hydrazinyl]-3-methoxyphenyl]-2-methoxyphenyl]hydrazinylidene]-5-oxonaphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C\1=CC2=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C(N)=C2C(=O)C/1=N/NC(C(OC)=C1)=CC=C1C1=CC=C(N\N=C\2C(C3=C(N)C(=CC(=C3C=C/2)S([O-])(=O)=O)S([O-])(=O)=O)=O)C(OC)=C1 UPKAWFACSJWKND-ZXFFUEEESA-J 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 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
- C09B29/16—Naphthol-sulfonic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
fi'vz. fi'vz. OO
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 197035 KLASSE 22«. GRUPPE- M 197035 CLASS 22 «. GROUP
Patentiert im Deutschen Reiche vom 17. April 1907 ab. Patented in the German Empire on April 17, 1907 .
In der Patentschrift 135015 ist ein Verfahren zur Darstellung alkylierter Monoazofarbstoffe beschrieben, welches darin besteht, daß man zunächst den Nitroazofarbstoff ausIn patent 135015 is a method described for the preparation of alkylated monoazo dyes, which consists in that you first off the nitroazo dye
. 5 o-Chlor-p-nitranilin und 1· 8-Dioxynaphtha-Hn-3 · 6-disulfosäure (Chromotropsäure) herstellt, den so gewonnenen Nitroazofarbstoff mit Schwefelnatrium reduziert und den dabei resultierenden Aminoazofarbstoff schließlich mit Alkylierungsmitteln, wie Brpmäthyl, behandelt. Wie in' der Patentschrift hervorgehoben wird, werden so Monoalkylderivate gewonnen.. 5 o-chloro-p-nitroaniline and 1x8-dioxynaphtha-Hn-3 Produces 6-disulfonic acid (chromotropic acid), the nitroazo dye obtained in this way is reduced with sodium sulphide and the resulting aminoazo dye finally treated with alkylating agents such as bromethyl. As highlighted in 'the patent specification is, so monoalkyl derivatives are obtained.
Es wurde nun gefunden, daß man in wesentlich einfacherer Weise zu den in jener Patentschrift nicht beschriebenen dialkylierten Monoazofarbstoffe^ gelangt, wenn man die Diazoverbindungen der bisher unbekannten p-Amino-m-chlordialkylaniline mit Chromotropsäure . kuppelt. Die erwähnten neuen Basen werden leicht erhalten, indem man die Nitrosoverbindungen der m-Chlordialkylaniline mit Zinkstaub und Salzsäure reduziert.It has now been found that it is much easier to get to those in that Dialkylated monoazo dyes not described in patent specification ^ arrives if you the Diazo compounds of the previously unknown p-amino-m-chlorodialkylanilines with chromotropic acid . clutch. The new bases mentioned are easily obtained by adding the Nitroso compounds of m-chlorodialkylanilines reduced with zinc dust and hydrochloric acid.
Das p- Amino-m-chlordimethylanilin bildet weiße Kristalle, die sich an der Luft bald grau färben. Schmelzpunkt 420, Siedepunkt 1580 bei 15 mm. Es ist schwer löslich in Wasser und leicht löslich in Säuren und organischen Lösungsmitteln.The p-amino-m-chlorodimethylaniline forms white crystals that soon turn gray when exposed to air. Melting point 42 0 , boiling point 158 0 at 15 mm. It is sparingly soluble in water and easily soluble in acids and organic solvents.
Das p-Amino-m-chlordiäthylanilin ist eine wasserhelle Flüssigkeit, die beim Stehen braun wird. Siedepunkt 285 ° bei 760 mm. Es ist schwer löslich in Wasser, leicht löslich in Säuren und organischen Lösungsmitteln.The p-amino-m-chlorodiethylaniline is one water-white liquid that turns brown when standing. Boiling point 285 ° at 760 mm. It is Slightly soluble in water, easily soluble in acids and organic solvents.
3535
17 kg p-Amino-m-chlordimethylanilin werden mit Hilfe von 40 kg Salzsäure und 6,9 kg Natriumnitrit in üblicher Weise diazotiert. Die so erhaltene Diazoverbindung wird darauf zu einer gut gekühlten Lösung von 36,2 kg Chromotropsäure (neutrales Natronsalz) in 360 1 Wasser und 8 kg Natronhydrat züge-. fügt. Man gibt darauf noch 40 kg Natronlauge von' 25 Prozent hinzu. Nach kurzer Zeit ist die Kuppelung beendet. Nach dem Ansäuern mit Salzsäure fällt der Farbstoff aus, er wird abgesaugt und getrocknet. Er färbt Wolle in sehr lebhaften reinblauen, licht- und alkaliechten Tönen an.17 kg of p-amino-m-chlorodimethylaniline will be diazotized in the usual way using 40 kg of hydrochloric acid and 6.9 kg of sodium nitrite. The diazo compound thus obtained then becomes a well-cooled solution of 36.2 kg Chromotropic acid (neutral sodium salt) in 360 l of water and 8 kg of sodium hydrate. adds. 40 kg of caustic soda are then added of '25 percent added. The coupling is finished after a short time. After this Acidification with hydrochloric acid precipitates the dye, it is filtered off with suction and dried. He colors wool in very lively, pure blue, light and alkali-proof tones.
Vor dem in dem erloschenen Patent 74738 beschriebenen Farbstoff aus unchloriertem p-Aminodimethylanilin zeichnet sich das neue Produkt durch wesentlich größere Alkaliechtheit und schönere Nuance aus. Auch verläuft die Farbstoffkuppelung bei der Anwendung der chlorierten Basen wesentlich glatter und mit viel besserer Ausbeute.Before that in the expired patent 74738 described dye from unchlorinated p-aminodimethylaniline is characterized by the new one Product is characterized by its significantly greater alkali fastness and nicer nuance. Also runs the dye coupling when using the chlorinated bases is much smoother and with much better yield.
Der Farbstoff aus p-Amino-m-chlordiäthylanilin färbt Wolle ebenfalls blau.The dye from p-amino-m-chlorodiethylaniline also dyes wool blue.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT36216D AT36216B (en) | 1907-04-16 | 1908-04-09 | Process for the preparation of blue monoazo dyes. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE197035C true DE197035C (en) |
Family
ID=459958
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1907197035D Expired - Lifetime DE197035C (en) | 1907-04-16 | 1907-04-16 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE197035C (en) |
-
1907
- 1907-04-16 DE DE1907197035D patent/DE197035C/de not_active Expired - Lifetime
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