DE243685C - - Google Patents
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- Publication number
- DE243685C DE243685C DENDAT243685D DE243685DA DE243685C DE 243685 C DE243685 C DE 243685C DE NDAT243685 D DENDAT243685 D DE NDAT243685D DE 243685D A DE243685D A DE 243685DA DE 243685 C DE243685 C DE 243685C
- Authority
- DE
- Germany
- Prior art keywords
- aminonaphthol
- phosgene
- acids
- sulfonic acids
- mol
- 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.)
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- YGYAWVDWMABLBF-UHFFFAOYSA-N phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- HMNPDEGBVWDHAR-UHFFFAOYSA-N 8-aminonaphthalen-1-ol Chemical compound C1=CC(O)=C2C(N)=CC=CC2=C1 HMNPDEGBVWDHAR-UHFFFAOYSA-N 0.000 claims description 3
- 235000013877 carbamide Nutrition 0.000 claims description 3
- ZWZVWGITAAIFPS-UHFFFAOYSA-N Thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- HONMCSLFRKBQHG-UHFFFAOYSA-N 1,3-diamino-1,3-diphenylurea Chemical compound C=1C=CC=CC=1N(N)C(=O)N(N)C1=CC=CC=C1 HONMCSLFRKBQHG-UHFFFAOYSA-N 0.000 claims 1
- 239000000987 azo dye Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 1
- 150000003585 thioureas Chemical class 0.000 claims 1
- 239000002253 acid Substances 0.000 description 9
- -1 aminonaphthol sulfonic acids Chemical class 0.000 description 8
- 239000000975 dye Substances 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 5
- 239000003929 acidic solution Substances 0.000 description 3
- 230000000875 corresponding Effects 0.000 description 3
- 230000001808 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-Nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- OSKOVOHYJXHSSL-UHFFFAOYSA-M [Cl-].[O-][N+](=O)C1=CCC(=[N+]=[N-])C=C1 Chemical compound [Cl-].[O-][N+](=O)C1=CCC(=[N+]=[N-])C=C1 OSKOVOHYJXHSSL-UHFFFAOYSA-M 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
- VDCZKCIEXGXCDJ-UHFFFAOYSA-N 3-methyl-2-nitroaniline Chemical compound CC1=CC=CC(N)=C1[N+]([O-])=O VDCZKCIEXGXCDJ-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
- POKAEVPBUOLQIY-UHFFFAOYSA-N 5-chloro-2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=C(Cl)C=C1N POKAEVPBUOLQIY-UHFFFAOYSA-N 0.000 description 1
- HHXLXWHFCCNQCO-UHFFFAOYSA-N 5-diazo-6-nitrocyclohexa-1,3-diene Chemical compound [O-][N+](=O)C1C=CC=CC1=[N+]=[N-] HHXLXWHFCCNQCO-UHFFFAOYSA-N 0.000 description 1
- 241000947840 Alteromonadales Species 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N Sodium sulfide Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- UXFFLQZHEKJOSN-UHFFFAOYSA-N [N+](=O)([O-])NC1=C(O)C=CC(=C1)O Chemical compound [N+](=O)([O-])NC1=C(O)C=CC(=C1)O UXFFLQZHEKJOSN-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- QMTFICBPEVWVIE-UHFFFAOYSA-N carbonyl dichloride;urea Chemical class NC(N)=O.ClC(Cl)=O QMTFICBPEVWVIE-UHFFFAOYSA-N 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- CZZVSJPFJBUBDK-UHFFFAOYSA-N diazonio-(4-nitrophenyl)azanide Chemical compound [O-][N+](=O)C1=CC=C([N-][N+]#N)C=C1 CZZVSJPFJBUBDK-UHFFFAOYSA-N 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000001046 green dye Substances 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 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 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts 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
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 243685 -■ KLASSE 22 a. GRUPPE- M 243685 - ■ CLASS 22 a. GROUP
harnstoff ableiten.Derive urea.
Patentiert im Deutschen Reiche vom 21. April 1910 ab.Patented in the German Empire on April 21, 1910.
Durch Behandeln von p-Aminobenzolazoarylsulfo- oder -carbonsäuren in wässeriger Lösung bei Gegenwart von Alkalien mit Phosgen sind mehrfach Harnstoffderivate erhalten worden (vgl. die Patentschriften 46737 und 216666). Auch Farbstoffe aus Aminonaphtolsulfosäuren wurden dem gleichen Verfahren unterworfen, doch fanden hierbei ß-Aminoa-naphtolderivate Verwendung, β-Amino-αϊ ο naphtolsulfosäuren selbst lassen sich bekanntlich leicht mittels Phosgen zu Harnstoffen verketten, während die Periaminonaphtolsulfosäuren zum gleichen Zwecke nicht brauchbar sind,, weil hier offenbar das Phosgen unter Ringschluß mit der Amino- oder Hydroxylgruppe gleichzeitig reagiert (vgl. die Patentschrift 116200). Es war daher anzunehmen, daß auch die Farbstoffe der 1 · 8-Aminonaphtolsulfosäuren sich analog verhalten würden. Demgegenüber wurde jedoch gefunden, daß sich die p-Aminobenzolazo-i · 8-aminonaphtolsulfosäuren, die sich z. B. durch Kuppeln von p-Nitrodiazobenzolchlorid mit 1 · 8-Aminonaphtolsulfosäuren in saurer Lösung und Reduktiön oder aus diazotierten Acidyl-p-diaminen durch Vereinigen mit den genannten Säuren und nachheriges Verseifen erhalten lassen, mittels Phosgen bei Gegenwart von Alkalien oder alkalisch wirkenden Salzen in normale Harnstoffderivate übergeführt werden können. Die so gebildeten Farbstoffe besitzen die Fähigkeit, Baumwolle direkt in braunen Tönen anzufärben und die wertvolle Eigenschaft, beim Entwickeln auf der Faser mit Nitrodiazobenzol in waschechte, gut ätzbare und sehr lichtechte grüne Farbstoffe überzugehen. Die gleichen Eigenschaften besitzen auch die gemischten Farbstoffe, die durch Behandeln von ι Mol. einer der oben erwähnten Aminobenzolazo -1 · 8 - aminonaphtolsulfosäuren und ι Mol. einer anderen p-Aminobenzolazoarylsulfo- oder -carbonsäure mittels Phosgen erhalten werden.By treating p-aminobenzolazoarylsulfo- or carboxylic acids in aqueous solution in the presence of alkalis with phosgene urea derivatives have been obtained several times (cf. patents 46737 and 216666). Also dyes made from aminonaphthol sulfonic acids were made using the same procedure subjected, but found this ß-Aminoa-naphtolderivate Use, β-amino-αϊ As is known, naphthol sulfonic acids themselves can easily be converted into ureas using phosgene chain, while the periaminonaphthol sulfonic acids cannot be used for the same purpose are ,, because here apparently the phosgene with ring closure with the amino or hydroxyl group reacts at the same time (see. Patent 116200). It was therefore to be assumed that the dyes of the 1 × 8-aminonaphthol sulfonic acids would behave analogously. In contrast, it was found that the p-aminobenzolazo-i · 8-aminonaphthol sulfonic acids, which z. By coupling p-nitrodiazobenzene chloride with 1x8-aminonaphthol sulfonic acids in acidic solution and reduction or from diazotized acidyl-p-diamines can be obtained by combining with the acids mentioned and subsequent saponification, by means of phosgene in the presence of alkalis or alkaline salts in normal Urea derivatives can be converted. The dyes thus formed have the Ability to dye cotton directly in brown tones and the valuable property when developing on the fiber with nitrodiazobenzene in washable, easily etchable and very lightfast green dyes to pass over. They have the same properties mixed dyes obtained by treating ι Mol. One of the above-mentioned aminobenzolazo -1 · 8 - aminonaphthol sulfonic acids and ι mol. Another p-aminobenzolazoarylsulfo- or carboxylic acid can be obtained by means of phosgene.
4545
Beispiel ι.Example ι.
46 kg des sauren Natriumsalzes der p-Aminobenzolazo-i · 8-aminonaphtol-4 · 6-disulfosäure, das durch Vereinigen von ι Mol. p-Nitrodiazobenzolchlorid mit ι Mol. ι · 8-Aminonaphtol-4 · 6-disulfosäure in saurer Lösung und Reduktion des entstandenen Monoazofarbstoffes mit Schwefelnatrium erhalten werden kann, werden mittels 34,5 kg Soda in 3450 1 heißem Wasser gelöst, ein Strom von Phosgengas wird so lange eingeleitet, bis der Aminoazokörper vollständig verschwunden ist. Hierauf wird so lange gerührt, bis der Geruch nach Phosgen nicht mehr wahrnehmbar ist, alsdann wird auf 75 ° erwärmt und das entstandene Harnstoffderivat ausgesalzen und abgepreßt.46 kg of the acidic sodium salt of p-aminobenzolazo-i · 8-aminonaphthol-4 · 6-disulfonic acid, which is obtained by combining ι mol. P-nitrodiazobenzene chloride with ι Mol. ι · 8-aminonaphthol-4 · 6-disulfonic acid in acidic solution and reduction of the resulting monoazo dye can be obtained with sodium sulphide, 34.5 kg of soda are dissolved in 3450 l of hot water, a stream of phosgene gas is initiated until the aminoazo body has completely disappeared. On that is stirred until the odor of phosgene is no longer perceptible, then it is heated to 75 ° and the resulting Urea derivative salted out and pressed.
23 kg desjenigen Aminoazokörpers, der durch Kupplung von 1 Mol. p-Nitrodiazobenzolchlorid mit ι Mol. ι · 8-Aminonaphtol-3 · 6-disulfosäure in saurer Lösung und alkalische Reduktion mittels Schwefelnatrium entsteht, sowie 14,4 kg23 kg of that aminoazo body obtained by coupling 1 mole of p-nitrodiazobenzene chloride with ι Mol. ι · 8-aminonaphthol-3 · 6-disulfonic acid in acidic solution and alkaline reduction by means of sodium sulfur, as well as 14.4 kg
ρ - aminobenzolazosalicylsaures Natrium werden in 3450 1 warmem Wasser unter Zusatz von 34,5 kg Soda oder der äquivalenten -Menge eines Ätzalkalis oder Acetats gelöst und bei 50 ° so lange der Einwirkung von Phosgen unterworfen, bis die Bildung des Harnstoffderivates beendigt ist. Man läßt nun erkalten, salzt mit 350 kg Salz aus und preßt und trocknet den Farbstoff, der direkt auf Baumwolle mit braunroter Farbe zieht und durch Einwirken von Diazo-p-nitranilin ein lebhaftes licht- und waschechtes Grün ergibt, das sich rein weiß ätzen läßt.ρ - aminobenzolazosalicylsaures sodium are added in 3450 1 warm water dissolved by 34.5 kg of soda or the equivalent amount of a caustic alkali or acetate and subjected to the action of phosgene at 50 ° until the formation of the Urea derivative is terminated. It is now allowed to cool, salted out with 350 kg of salt and presses and dries the dye, which pulls directly onto cotton with a brownish-red color and by the action of diazo-p-nitroaniline results in a lively light- and washfast green, that can be etched in pure white.
An Stelle der in den Beispielen erwähnten ρ - Aminobenzolazo -1 · 8-aminonaphtoldisulfosäuren können auch deren Homologe und Substitutionsprodukte genommen werden, z. B. Aminotoluolazo -1 · 8-aminonaphtoldisulfosäuren (aus o-Nitro-m-toluidin oder m-Nitro-otoluidin oder den entsprechenden Acidyltoluylendiaminen), ferner die aus Nitrokresidin, aus 3-Nitro-4-chlor-6-aminoanisol, sowie aus Nitroaminohydrochinon durch Diazotieren und Kuppeln mit den 1 · 8-Aminonaphtoldisulfosäuren und nachherige Reduktion entstehenden Aminoverbindungen. Ferner können die entsprechenden Farbstoffe aus Aminonaphtolmonosulfosäuren benutzt werden; in diesem Falle lassen sich an Stelle von p-Nitranilin usw. auch die Sulfosäuren des p-Nitranilins oder die entsprechenden Acidyl-p-phenylendiaminsulfosäuren verwenden. ■Instead of the ρ-aminobenzolazo -1 · 8-aminonaphthol disulfonic acids mentioned in the examples their homologues and substitution products can also be used, e.g. B. Aminotoluene azo -1 x 8-aminonaphthol disulfonic acids (from o-nitro-m-toluidine or m-nitro-otoluidine or the corresponding acidyltoluylenediamines), also from nitrocresidine, from 3-nitro-4-chloro-6-aminoanisole, and from nitroaminohydroquinone by diazotization and Coupling with the 1x8-aminonaphthol disulfonic acids and subsequent reduction resulting amino compounds. The corresponding dyes can also be obtained from aminonaphthol monosulfonic acids to be used; in this case, instead of p-nitroaniline etc. also the sulfonic acids of p-nitroaniline or the corresponding acidyl-p-phenylenediamine sulfonic acids use. ■
Die im Beispiel 2 erwähnte p-Aminobenzolazosalicylsäure läßt sich ersetzen durch die in der Patentschrift 216666 genannten Azokörper, die sich aus Diazosulfo- oder -carbonsäuren. und Anilin, 0- oder m -Toluidin, p-Xyiidin und Kresidin erhalten lassen.The p-aminobenzolazosalicylic acid mentioned in Example 2 can be replaced by the azo bodies mentioned in patent 216666, which consist of diazosulfo- or carboxylic acids. and aniline, 0- or m -toluidine, Let p-xyiidin and cresidin be obtained.
Das Phosgen kann durch Thiophosgen oder diejenigen Derivate ersetzt werden, die zu gleichen Ergebnissen führen.The phosgene can be replaced by thiophosgene or those derivatives that lead to lead to the same results.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE243685C true DE243685C (en) |
Family
ID=502790
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT243685D Active DE243685C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE243685C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3976320A (en) * | 1975-08-14 | 1976-08-24 | The United States Of America As Represented By The Secretary Of Agriculture | Chicken coop lifting device |
-
0
- DE DENDAT243685D patent/DE243685C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3976320A (en) * | 1975-08-14 | 1976-08-24 | The United States Of America As Represented By The Secretary Of Agriculture | Chicken coop lifting device |
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