DE240163C - - Google Patents
Info
- Publication number
- DE240163C DE240163C DENDAT240163D DE240163DA DE240163C DE 240163 C DE240163 C DE 240163C DE NDAT240163 D DENDAT240163 D DE NDAT240163D DE 240163D A DE240163D A DE 240163DA DE 240163 C DE240163 C DE 240163C
- Authority
- DE
- Germany
- Prior art keywords
- diazotized
- parts
- hydrochloric acid
- amino group
- phosgene
- 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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
- 230000000875 corresponding Effects 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- -1 Aminoazo compounds Chemical class 0.000 claims description 2
- ZWZVWGITAAIFPS-UHFFFAOYSA-N Thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- 239000000987 azo dye Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 150000003460 sulfonic acids Chemical class 0.000 claims description 2
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 claims 1
- 235000013877 carbamide Nutrition 0.000 claims 1
- 230000001808 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 239000000975 dye Substances 0.000 description 9
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 4
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-Nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 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 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-Xylidine Chemical group CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 1
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 1
- QYFYIOWLBSPSDM-UHFFFAOYSA-N 6-aminonaphthalen-1-ol Chemical compound OC1=CC=CC2=CC(N)=CC=C21 QYFYIOWLBSPSDM-UHFFFAOYSA-N 0.000 description 1
- 241000947840 Alteromonadales Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- YXXATGUUTCQCCD-UHFFFAOYSA-N NC1=C(C2=C(N=C(N2)S(=O)(=O)O)C2=CC=CC=C12)OC1=CC=CC=C1 Chemical class NC1=C(C2=C(N=C(N2)S(=O)(=O)O)C2=CC=CC=C12)OC1=CC=CC=C1 YXXATGUUTCQCCD-UHFFFAOYSA-N 0.000 description 1
- WXWCDTXEKCVRRO-UHFFFAOYSA-N Para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003672 ureas Chemical class 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
- C09B43/14—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents with phosgene or thiophosgene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Gelöscht aDeleted a
1913 Ms,1913 Ms,
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 240163 KLASSE 22 a. GRUPPE- M 240163 CLASS 22 a. GROUP
Verfahren zur Darstellung von Azofarbstoffen. Patentiert im Deutschen Reiche vom 14. August 1910 ab.Process for the preparation of azo dyes. Patented in the German Empire on August 14, 1910.
Es wurde gefunden, daß man zu neuen, wertvollen Farbstoffen gelangt, wenn man diazotierte Amirionaphtole oder deren Sulfosäuren oder diazotierbare, in der Aminogruppe substituierte Derivate dieser Verbindungen, z. B. Aminobenzoyl-aminonapbtolsulfosäuren oderAminophenyl-oxynaphtimidazolsulfosäuren usw., mit aromatischen Aminen zu Aminoazofarbstoffen vereinigt und diese durch Phosgen,It has been found that new, valuable dyes can be obtained by diazotized amirionaphthols or their sulfonic acids or diazotizable ones in the amino group substituted derivatives of these compounds, e.g. B. aminobenzoyl-aminonapbtolsulfonic acids or aminophenyl-oxynaphthimidazole sulfonic acids, etc., with aromatic amines to form aminoazo dyes united and this by phosgene,
ίο Thiophosgen oder ihre Ersatzprodukte in die entsprechenden Harnstoffderivate überführt.ίο Thiophosgene or its substitutes in the corresponding urea derivatives transferred.
Die Farbstoffe zeichnen sich dadurch aus, daß sie unmittelbar auf Baumwolle ziehen, und daß ihre mit diazotierten Aminen, z. B.The dyes are characterized by the fact that they pull directly onto cotton, and that their diazotized amines, e.g. B.
mit diazotierten! p-Nitranilin nachbehandelten Färbungen sehr gute Ätzbarkeit und Waschechtheit aufweisen.with diazotized! p-Nitraniline aftertreated dyeings have very good etchability and washfastness exhibit.
239 Teile 1 · 6 - Aminonaphtol - 3 - sulfosäure werden mit 69 Teilen Natriumnitrit und Salzsäure diazotiert und in ganz schwach salzsaurer Lösung mit 187,5 Teilen Kresidinchlorhydrat vereinigt. Der Monoazofarbstoff wird aus salzsaurer Lösung isoliert und mit überschüssiger Soda gelöst. In die Lösung wird bei 40 ° Phosgen eingeleitet, bis kein unveränderter Farbstoff mehr nachzuweisen ISt1 wobei darauf zu achten ist, daß die Lösung immer alkalisch reagiert. Darauf wird der Farbstoff ausgesalzen und isoliert. Die direkte Färbung auf Baumwolle ist orangefarben. Sie geht durch Nachbehandlung mit diazotiertem p-Nitranilin in ein gut ätzbares,, waschechtes Braunrot von hervorragender LichtecLtheit über.239 parts of 1 · 6 - aminonaphthol - 3 - sulfonic acid are diazotized with 69 parts of sodium nitrite and hydrochloric acid and combined with 187.5 parts of cresidine chlorohydrate in a very weak hydrochloric acid solution. The monoazo dye is isolated from hydrochloric acid solution and dissolved with excess soda. Phosgene is passed into the solution at 40 ° until no more unchanged dye can be detected ISt 1, whereby it must be ensured that the solution always has an alkaline reaction. The dye is then salted out and isolated. The direct dye on cotton is orange. After treatment with diazotized p-nitroaniline, it changes into a well-etchable, washable brown-red of excellent lightness.
355 Teile m-Aminophenyl-s-oxy^-naphtimidazol-7-sulfosäure werden mit 69Teilen Natriumnitrit und Salzsäure diazotiert und in ganz schwach salzsaurer Lösung mit 121 Teilen p-Xylidin gekuppelt. Der Monoazofarbstoff wird aus salzsaurer Lösung in der Wärme isoliert und sodaalkalisch gelöst. In die beständig alkalisch gehaltene Lösung wird bei 40 ° Phosgen eingeleitet bis zur vollständigen Überführung in den Harnstoff, der dabei ausfällt. Er färbt Baumwolle mit gelber Nuance an, die bei Nachbehandlung mit diazotiertem p-Nitranilin in ein gut ätzbares und waschechtes Rot übergeht.355 parts of m-aminophenyl-s-oxy ^ -naphtimidazole-7-sulfonic acid are diazotized with 69 parts of sodium nitrite and hydrochloric acid and in very weak hydrochloric acid solution coupled with 121 parts of p-xylidine. The monoazo dye is isolated from a hydrochloric acid solution in the warmth and dissolved in a soda-alkaline solution. In the constantly alkaline solution is introduced at 40 ° phosgene until it is complete Conversion into the urea, which precipitates in the process. It dyes cotton with a yellow shade, which after treatment with diazotized p-Nitraniline turns into a readily etchable and washable red.
358 Teile m-Aminobenzoyl^s-aminonaphtol-7-sulfosi.ure werden mit 69 Teilen Natriumnitrit und Salzsäure diazotiert und in ganz schwach salzsaurer Lösung mit 107 Teilen m-Toluidin gekuppelt. Der Monoazofarbstoff wird salzsauer in der Wärme isoliert und nach Beispiel 2 in den entsprechenden Harnstoff übärgeführt. Seine direkte Färbung auf Baumwolle ist gelb; sie wird durch Nachbehandlung mit diazotiertem p-Nitranilin in ein gut ätz bares und waschechtes Orange übergeführt. 358 parts of m-aminobenzoyl-s-aminonaphtol-7-sulfosi.ure are diazotized with 69 parts of sodium nitrite and hydrochloric acid and in very weak hydrochloric acid solution with 107 parts m-toluidine coupled. The monoazo dye is isolated in the heat and in hydrochloric acid in accordance with example 2 converted into the corresponding urea. Its direct coloring on Cotton is yellow; it is converted into a well etchable and real orange transferred.
Claims (1)
Aminoazoverbindungen, die aus diazotierten Aminonaphtolen oder deren Sulfosäuren oder aus diazotierten, in der Amino-Process for the preparation of azo dyes, consisting in that one such
Aminoazo compounds, which are made from diazotized aminonaphthols or their sulfonic acids or from diazotized, in the amino
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE240163C true DE240163C (en) |
Family
ID=499549
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT240163D Active DE240163C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE240163C (en) |
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0
- DE DENDAT240163D patent/DE240163C/de active Active
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