DE81109C - - Google Patents
Info
- Publication number
- DE81109C DE81109C DENDAT81109D DE81109DA DE81109C DE 81109 C DE81109 C DE 81109C DE NDAT81109 D DENDAT81109 D DE NDAT81109D DE 81109D A DE81109D A DE 81109DA DE 81109 C DE81109 C DE 81109C
- Authority
- DE
- Germany
- Prior art keywords
- pyrogallol
- amidophenol
- acid
- dyes
- brown
- 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 24
- 229940079877 Pyrogallol Drugs 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 239000000987 azo dye Substances 0.000 claims description 5
- 150000008049 diazo compounds Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims 1
- 239000000975 dye Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 150000003460 sulfonic acids Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- FCWPLGWNMBKCKT-UHFFFAOYSA-N 4-diazocyclohexa-1,5-dien-1-ol Chemical compound OC1=CCC(=[N+]=[N-])C=C1 FCWPLGWNMBKCKT-UHFFFAOYSA-N 0.000 description 2
- MFCDHQNPTNBIGC-UHFFFAOYSA-N 6-diazocyclohexa-2,4-diene-1-carboxylic acid Chemical class OC(=O)C1C=CC=CC1=[N+]=[N-] MFCDHQNPTNBIGC-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- ZIPJXJGTIGXUSE-UHFFFAOYSA-N 6-diazocyclohexa-2,4-dien-1-ol Chemical compound OC1C=CC=CC1=[N+]=[N-] ZIPJXJGTIGXUSE-UHFFFAOYSA-N 0.000 description 1
- 241000322338 Loeseliastrum Species 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- GPOARVJSTGCBPO-UHFFFAOYSA-N [N+](=[N-])=C1CC(=C(C(=O)O)C=C1)O Chemical compound [N+](=[N-])=C1CC(=C(C(=O)O)C=C1)O GPOARVJSTGCBPO-UHFFFAOYSA-N 0.000 description 1
- KZBAMMZXQMYEOE-UHFFFAOYSA-N [N+](=[N-])=C1CC(=CC=C1)O Chemical class [N+](=[N-])=C1CC(=CC=C1)O KZBAMMZXQMYEOE-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000020127 ayran Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 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
- 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
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Aus Pyrogallol sind schon mehrfach Azofarbstoffe erhalten worden. Arbeitet man jedoch z. B. nach Stebbins, Ber. XIII, S. 44 und 574, oder nach dem französischen Patent Nr. 211374, so erhält man nur werthlose Producte.Azo dyes have already been obtained several times from pyrogallol. But if you work z. B. after Stebbins, Ber. XIII, pp. 44 and 574, or according to French patent No. 211374, thus one only receives worthless products.
Die glatte Herstellung von Azofarbstoffen aus Pyrogallol wurde bis jetzt nur durch Einwirkung von Diazobenzoesäuren in mineralsaurer Lösung, nach Art der Bildung von Amidoazofarbstoffen, erzielt zufolge Patent Nr. 66975.The smooth production of azo dyes from pyrogallol has so far only been achieved by exposure of diazobenzoic acids in mineral acid solution, like the formation of amidoazo dyes, achieved according to patent No. 66975.
In dieser Patentschrift findet sich auch die mit den bisherigen Erfahrungen übereinstimmende Angabe, dafs insbesondere alle Diazoverbindungen, welche zur Combination freies Alkali erfordern, zur Herstellung von Azofarbstoffen mit Pyrogallol nicht geeignet seien. .This patent specification also contains the one that corresponds to previous experience Specification that in particular all diazo compounds which require free alkali for combination for the production of Azo dyes with pyrogallol are not suitable. .
Im Gegensatz zu dieser Angabe wurde nun gefunden, dafs eine gewisse Klasse von Diazoverbindungen, nämlich diejenigen der p-Amidophenole, deren Carbonsäuren und Sulfosäuren, sich in alkalischer Lösung glatt mit Pyrogallol vereinigen lassen. In saurer Lösung, nach dem Verfahren des Patentes Nr. 66975, findet dagegen die Farbstoffbildung nicht statt.In contrast to this statement, it has now been found that a certain class of diazo compounds namely those of the p-amidophenols, their carboxylic acids and sulfonic acids, in alkaline solution smoothly with pyrogallol let unite. In acidic solution, according to the method of patent no. 66975, on the other hand, takes place the dye formation does not take place.
Bemerkenswert!} ist noch, dafs diazotirtes o-Amidophenol, sowie o-Diazophenolsulfosäure ebenfalls unter Bildung von Azofarbstoffen reagiren, die jedoch nur von geringem Werth sind, während die m-Diazophenole und deren Sulfosäuren überhaupt nicht fähig sind, sich in alkalischer Lösung mit Pyrogallol zu vereinigen.It is also noteworthy that diazotized o-amidophenol and o-diazophenol sulfonic acid also react with the formation of azo dyes, but these only slightly Are worth while the m-diazophenols and their sulfonic acids are not at all capable to combine in alkaline solution with pyrogallol.
Nach diesem Verfahren werden werthvolle Farbstoffe erhalten, welche auf chromgebeizter Faser intensiv braune Töne erzeugen, die sich durch Walkechtheit auszeichnen. Mittelst Thonerdebeizen erhält man weniger intensive, mit Eisenbeizen grauere Nuancen. Von den gelbbraunen Farbstoffen des Patentes Nr. 66975 unterscheiden sich die neuen Producte durch ganz andere, viel rothere und dunklere Farbtöne; ferner eignen sich die Farbstoffe aus den Amidophenolsulfosäuren in vorzüglicher Weise zum Kattundruck, was bei den Farbstoffen aus den Diazobenzoesäuren nicht der Fall ist.This process gives valuable dyes which are stained with chrome Fibers produce intense brown tones, which are characterized by their fastness to flexing. Middle clay pickling you get less intense, with iron stains grayer nuances. Of the tan dyes of patent no. 66975 the new products differ by quite different, much redder and darker hues; the dyes from the amidophenol sulfonic acids are also particularly suitable for calico printing, which is not the case with the dyes from the diazobenzoic acids.
Die folgenden Producte haben sich als technisch werthvoll erwiesen:The following products have proven to be technically valuable:
p-Diazophenol und Pyrogallol, Nuance auf chromgebeizter Wolle: rothbraun,p-diazophenol and pyrogallol, shade up chrome-stained wool: red-brown,
p-Diazosalicylsäure und Pyrogallol: dunkelbraun, p-diazosalicylic acid and pyrogallol: dark brown,
p-Diazophenolmonosulfosäure und Pyrogallol: braun,p-diazophenol monosulfonic acid and pyrogallol: brown,
α-p-Diazophenoldisulfosäure (PatentNr.6 5 236) und Pyrogallol: rothbraun.α-p-Diazophenol disulfonic acid (Patent No. 6 5 236) and pyrogallol: red-brown.
Die Farbstoffe aus. p-Amidophenol und ρ-Amidosalicylsäure sind sehr leicht in Alkalien mit brauner Farbe löslich und werden durch Säuren in dunklen Flocken gefällt; diejenigen aus den ρ-Amidophenolsulfosäuren werden durch Säuren nicht gefällt, sondern die braunen Lösungen dadurch hellgelb gefärbt. Charakteristisch für sämmtliche Farbstoffe ist, dafs sie sich in alkalischen Lösungen an der Luft leicht oxydiren, wobei dieselben mifsfarbig werden.The dyes off. p-Amidophenol and ρ-Amidosalicylic acid are very light in alkalis soluble in brown color and precipitated in dark flakes by acids; those from the ρ-amidophenol sulfonic acids are not precipitated by acids, but the brown ones Solutions colored light yellow as a result. It is characteristic of all dyes that they easily oxidize themselves in alkaline solutions in the air, whereby they become mif-colored.
I. Beispiel.I. Example.
11 kg ρ-Amidophenol werden mit 28 kg Salzsäure 210B. in 100 1 Wasser gelöst und unter Zusatz von Eis mit 7 kg Natriumnitrit11 kg of ρ-amidophenol are dissolved with 28 kg of hydrochloric acid 21 0 B. in 100 1 of water and with the addition of ice with 7 kg of sodium nitrite
diazotirt; alsdann wird eine Lösung von 13 kg Pyrogallol in 50 1 Wasser und hierauf von 25 kg Soda in iool Wasser hinzugefügt. Die intensiv dunkelbraun gewordene Lösung wird nach 12 stündigem Stehenlassen mit 5 5 kg Essigsäure von 40 pCt. übersättigt, der Farbstoff abfiltrirt und als Teig zur Verwendung gebracht.diazotized; then a solution of 13 kg Pyrogallol in 50 liters of water and then 25 kg of soda in iool water are added. the The solution which has become intensely dark brown becomes 5 kg after standing for 12 hours Acetic acid of 40 pCt. oversaturated, the dye filtered off and used as a dough brought.
II. Beispiel.II. Example.
30 kg saures Natronsalz der ct-p-Amidophenoldisulfosäure (Patent Nr. 65236) werden in 300 1 heifsem Wasser gelöst; die beim Erkalten dick gewordene Masse wird mit 50 kg Eis und 15 kg Salzsäure 210B. versetzt und mit 7 kg Natriumnitrit diazotirt; alsdann fällt man die theilweise in Lösung gegangene Diazoverbindung mit 50 kg Kochsalz aus und filtrirt dieselbe ab.30 kg of acidic sodium salt of ct-p-amidophenol disulfonic acid (Patent No. 65236) are dissolved in 300 liters of hot water; the mass, which has become thick on cooling, is mixed with 50 kg of ice and 15 kg of hydrochloric acid 21 0 B. and diazotized with 7 kg of sodium nitrite; the diazo compound, which has partially dissolved, is then precipitated with 50 kg of common salt and filtered off.
Der Teig wird mit 30 kg Eis verrührt und alsdann die Lösung von 12,5 kg Pyrogallol in 30 1 Wasser und unter gutem Rühren die Lösung von 18 kg Soda in 60 1 Wasser zugefügt. Die gebildete dicke, dunkelbraune Paste wird nach mehrstündigem Stehenlassen mittelst 50 kg Essigsäure von 40 pCt. angesäuert und der erhaltene hellbraune Teig entweder direct zum Färben und Drucken verwendet, oder der Farbstoff abfiltrirt, geprefst und bei 50 bis 6o° getrocknet.The dough is stirred with 30 kg of ice and then the solution of 12.5 kg of pyrogallol in 30 l of water and, with thorough stirring, the solution of 18 kg of soda in 60 l of water was added. The thick, dark brown paste formed is after standing for several hours with 50 kg acetic acid of 40 pCt. acidified and the light brown dough obtained is either used directly for dyeing and printing, or the dye is filtered off, pressed and dried at 50 to 60 °.
Claims (2)
Publications (1)
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