DE145908C - - Google Patents
Info
- Publication number
- DE145908C DE145908C DENDAT145908D DE145908DA DE145908C DE 145908 C DE145908 C DE 145908C DE NDAT145908 D DENDAT145908 D DE NDAT145908D DE 145908D A DE145908D A DE 145908DA DE 145908 C DE145908 C DE 145908C
- Authority
- DE
- Germany
- Prior art keywords
- sulfonic acid
- acid
- toluidine
- chloro
- dye
- 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
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims description 2
- -1 O-chloro-m-toluidine-p-sulfonic acid Chemical compound 0.000 claims 1
- 239000001044 red dye Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- GMADZPSIYOZBIB-UHFFFAOYSA-N 4-amino-3-chloro-2-methylbenzenesulfonic acid Chemical compound CC1=C(Cl)C(N)=CC=C1S(O)(=O)=O GMADZPSIYOZBIB-UHFFFAOYSA-N 0.000 description 3
- 150000008049 diazo compounds Chemical class 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- UPMIEBBZKWZYEZ-UHFFFAOYSA-N 3-chloro-4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1Cl UPMIEBBZKWZYEZ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- ZVKYMCJPJOWWRW-UHFFFAOYSA-N ClC1=C(C)C=CC(=C1[N+](=O)[O-])S(=O)(=O)O Chemical class ClC1=C(C)C=CC(=C1[N+](=O)[O-])S(=O)(=O)O ZVKYMCJPJOWWRW-UHFFFAOYSA-N 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L Iron(II) chloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000802 nitrating Effects 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-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
- C09B63/00—Lakes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paints Or Removers (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Es wurde gefunden, daß man einen schönen roten Azofarbstoff erhält, welcher sich sehr gut zur Darstellung roter Lacke eignet, indem man die Diazoverbindung der o-Chlorm-toluidin-p-sulfosäure umsetzt mit ß-Naphthol. It has been found that a beautiful red azo dye is obtained which is very different well suited for the representation of red lacquers by adding the diazo compound of o-chlorom-toluidine-p-sulfonic acid reacts with ß-naphthol.
Die bisher unbekannte o-Chlor-m-toluidinp-sulfosäure The previously unknown o-chloro-m-toluidine p-sulfonic acid
(CH3: NH2 (CH 3 : NH 2
Cl: SO3H--Cl: SO 3 H--
:3:6:4;: 3: 6: 4;
erhält man durch Reduktion der o-Chlor-mnitrotoluol-p-sulfosäure, welche ihrerseits durch Nitrieren der o-Chlortoluol-p-sulfosäureis obtained by reducing the o-chloro-mnitrotoluene-p-sulfonic acid, which in turn by nitrating the o-chlorotoluene-p-sulfonic acid
. zu erhalten ist. Während die Salze der m-Nitro-o-chlortoluol-p-sulfosäure in Wasser leicht löslich sind, sind die der reduzierten Säure bedeutent schwerer löslich und leicht in kristallisierter Form zu erhalten. Die o-Chlor-m-toluidin-p-sulfosäure bildet als freie Säure ein weißes Pulver, welches in Wasser ziemlich schwer löslich ist. Die Lösung der Säure in essigsaurem Natron wird durch Zusatz von Eisenchlorid braun gefärbt. Die Diazoverbindung ist fast farblos und fällt aus konzentrierter Lösung zum Teil aus.. is to be obtained. While the salts of m-nitro-o-chlorotoluene-p-sulfonic acid are readily soluble in water, those of the reduced acid are significantly less soluble and easy in crystallized form. The o-chloro-m-toluidine-p-sulfonic acid forms a white powder as the free acid, which is rather sparingly soluble in water. The solution to the Acid in baking soda turns brown when iron chloride is added. the Diazo compound is almost colorless and partially precipitates from concentrated solution.
Beispiel für die Darstellung des Farbstoffes: 22,15 kg o-Chlortoluidin-p-solfosäure werden in der äquivalenten Menge Soda gelöst, die Lösung schnell abgekühlt und so viel Salzsäure zugesetzt, daß die Masse . gerade sauer 3> reagiert. Die Sulfosäure scheidet sich als feines weißes Pulver aus. Man gibt darauf 22 kg Salzsäure von etwa 33 Prozent H Cl-Gehalt hinzu und diazotiert mit 7 kg Nitrit. Die Diazoverbindung fällt zum Teil aus. 3.s Darauf läßt man einlaufen in eine kalte Lösung von 14,6 kg ß-N.aphthol, gelöst in 12 kg Natronlauge von 400 B. und 10 kg Soda.- Nach etwa 12 Stunden abfiltriert und getrocknet bildet der Farbstoff in staubfeiner 4 > Form ein rotes Pulver, welches im Wasser nur in der Hitze etwas löslich ist. Die aus dem Farbstoff erhältlichen Lacke zeichnen sich durch ihre Nuance und Echtheit aus.Example for the representation of the dye: 22.15 kg of o-chlorotoluidine-p-solfonic acid are dissolved in the equivalent amount of soda, the solution is quickly cooled and so much hydrochloric acid is added that the mass. just angry 3> reacts. The sulfonic acid separates out as a fine white powder. 22 kg of hydrochloric acid with about 33 percent HCl content are then added and the mixture is diazotized with 7 kg of nitrite. The diazo compound fails in part. Then 3.s allowed to run into a cold solution of 14.6 kg ß-N.aphthol dissolved in 12 kg of sodium hydroxide of 40 and 10 kg 0 B. Soda.- filtered off after about 12 hours and dried in the dye forms fine dust 4> Form a red powder, which is only slightly soluble in water in the heat. The paints obtainable from the dye are distinguished by their nuance and authenticity.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE145908C true DE145908C (en) |
Family
ID=413225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT145908D Active DE145908C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE145908C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2955050A (en) * | 1956-07-17 | 1960-10-04 | Geigy Ag J R | Water fastness of metal lakes of azo dyestuffs containing sulphonic acid groups |
| US6228162B1 (en) | 1998-12-19 | 2001-05-08 | Clariant Gmbh | Process for preparing new crystal modifications of C.I. pigment red 53:2 |
| WO2003016408A1 (en) * | 2001-08-14 | 2003-02-27 | Clariant Gmbh | Pigmented 1-naphtholsulphonic acid-based monoazo pigments |
-
0
- DE DENDAT145908D patent/DE145908C/de active Active
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2955050A (en) * | 1956-07-17 | 1960-10-04 | Geigy Ag J R | Water fastness of metal lakes of azo dyestuffs containing sulphonic acid groups |
| US6228162B1 (en) | 1998-12-19 | 2001-05-08 | Clariant Gmbh | Process for preparing new crystal modifications of C.I. pigment red 53:2 |
| WO2003016408A1 (en) * | 2001-08-14 | 2003-02-27 | Clariant Gmbh | Pigmented 1-naphtholsulphonic acid-based monoazo pigments |
| US6984724B2 (en) | 2001-08-14 | 2006-01-10 | Clariant Gmbh | Pigmented 1-naphtholsulphonic acid-based monoazo pigments |
| KR100856181B1 (en) * | 2001-08-14 | 2008-09-03 | 클라리안트 프로두크테 (도이칠란트) 게엠베하 | Pigmented 1-naphtholsulphonic acid-based monoazo pigments |
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