DE108274C - - Google Patents
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- Publication number
- DE108274C DE108274C DENDAT108274D DE108274DA DE108274C DE 108274 C DE108274 C DE 108274C DE NDAT108274 D DENDAT108274 D DE NDAT108274D DE 108274D A DE108274D A DE 108274DA DE 108274 C DE108274 C DE 108274C
- Authority
- DE
- Germany
- Prior art keywords
- red
- water
- soluble
- sulfuric acid
- color
- 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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- 239000000975 dye Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 3
- 150000001454 anthracenes Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 210000002268 Wool Anatomy 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000001187 sodium carbonate Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- NMNSBFYYVHREEE-UHFFFAOYSA-N 1,2-dinitroanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C3C(=O)C2=C1 NMNSBFYYVHREEE-UHFFFAOYSA-N 0.000 description 1
- RZVHIXYEVGDQDX-UHFFFAOYSA-N Anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L Calcium hydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 235000015450 Tilia cordata Nutrition 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
- C09B1/325—Dyes with no other substituents than the amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE 22: Farbstoffe, Firnisse, Lacke.CLASS 22: dyes, varnishes, lacquers.
der Anthracenreihe.the anthracene series.
Patentirt im Deutschen Reiche vom 10. Dezember 1898 ab.Patented in the German Empire on December 10, 1898.
Es wurde beobachtet, dafs die in dem Patent 106227 genannten, durch Einwirkung von primären aromatischen Aminen auf Dinitroanthrachinone entstehenden und dort als Dialphylido- (Dialphyldiamido-) anthrachinone bezeichneten Körper, welche für sich keinerlei Verwandtschaft zur Faser zeigen, durch sulfirende Mittel in werthvolle wasserlösliche Farbstoffe übergeführt werden können, welche auf der animalischen Faser lebhaft bordeauxfarbene und rothviolette bis gelbrothe Nuancen von ganz hervorragender Lichtechtheit liefern. Bei kürzerer bezw. gemäfsigter Einwirkung der Schwefelsäure entstehen violettroth - färbende Producte, welche relativ leicht aussalzbar sind. Läfst man hingegen die Schwefelsäure energischer auf die Dialphyldiamidoanthrachinone einwirken, indem man z. B. anhydridhaltige Schwefelsäure (etwa Oleum von 20 pCt. Anhydridgehalt) anwendet, so erhält man Sulfosäuren, welche durch Kochsalz oder durch Chlorkalium nicht oder weit schwieriger als die ersterwähnten ausgesalzen werden. Diese Säuren können z. B. isolirt werden, indem man sie in die Kalksalze überführt und diese dann mit Natriumcarbonat umsetzt, wodurch die Natriumsalze der Sulfosäuren erhalten werden.It has been observed that those mentioned in patent 106227, by action of primary aromatic amines on dinitroanthraquinones and there as Dialphylido- (dialphyldiamido-) anthraquinones designated body, which for themselves no Show affinity to fibers by sulphurizing agents into valuable water-soluble dyes which are vividly burgundy colored on the animal fiber can be transferred and deliver red-violet to yellow-red nuances of outstanding lightfastness. at shorter resp. moderate action of sulfuric acid produces violet-red coloring Products that are relatively easy to salt out. If, on the other hand, you let the sulfuric acid more vigorously act on the dialphyldiamidoanthraquinones by z. B. anhydride-containing Sulfuric acid (about oleum with an anhydride content of 20 pCt) is used, then sulfonic acids are obtained, which are not or far more difficultly salted out by table salt or by potassium chloride than the first mentioned. These Acids can e.g. B. be isolated by converting them into the calcium salts and then these reacts with sodium carbonate, whereby the sodium salts of the sulfonic acids are obtained.
Diese letzteren Sulfosäuren färben Wolle in saurem Bade gelbstichig roth.These latter sulfonic acids color wool in an acidic bath with a yellowish red tinge.
Zur Erläuterung des Verfahrens mögen folgende Beispiele dienen:The following examples may serve to explain the procedure:
100 kg ι · 5-Dianilidoanthrachinon werden mit 1000 kg Schwefelsäure von 660B. so lange" auf ca. 80 bis 1000C. erhitzt, bis sich eine Probe in heifsem Wasser leicht löst. Die erkaltete Schmelze wird hierauf in Wasser gegossen, mit wenig Kochsalz der Farbstoff abgeschieden, abfiltrirt, geprefst und getrocknet. Er bildet ein chokoladebraunes, in heifsem Wasser leicht mit rother Farbe lösliches Pulver; Zusatz von Natriumcarbonat oder Natronhydrat zur wässerigen Lösung ändert deren Farbe nicht. In Alkohol und warmem Anilin ist der Farbstoff mit kirschrother Farbe löslich; concentrirte Schwefelsäure löst ihn schmutzigbraun. Er färbt Wolle in violettrothen Tönen. 100 kg · ι 5-Dianilidoanthrachinon are heated with 1,000 kg of sulfuric acid of 66 0 B. so long "to about 80 to 100 0 C., until a sample in hot water readily dissolves. The cooled melt is then poured into water, with a little table salt the dye is separated, filtered off, pressed and dried. It forms a chocolate-brown powder which is easily soluble in hot water with a red color; the addition of sodium carbonate or sodium hydrate to the aqueous solution does not change its color. The dye is present in alcohol and warm aniline Soluble cherry-red color, concentrated sulfuric acid dissolves it in a dirty brown color, and dyes wool in violet-red tones.
10 kg des i· 5-Dianilidoanthrachinons werden in 100 kg Oleum von 20 pCt. Anhydridgehalt eingetragen und so lange bei 30 bis 350 C. gerührt, bis eine Probe in Wasser vollständig löslich geworden ist. Die Schmelze wird hierauf in Eiswasser gegossen, die Lösung mit Kalkmilch genau neutralisirt und der ausgeschiedene Gips abfiltrirt. Das Filtrat wird mit Natriumcarbonat umgesetzt, der ausgeschiedene kohlensaure Kalk abfiltrirt ,und das im Filtrat enthaltene Natronsalz der Sulfosäure durch Eindampfen in trockener Form gewonnen. Es bildet ein dunkelgefärbtes Pulver, in ,Wasser leicht mit gelbrother Farbe löslich, welche durch Natronlaugezusatz blaustichiger wird. In concentrirter Schwefelsäure löst sich der Farbstoff roth, in Alkohol und Anilin ist er so gut wie unlöslich. Er färbt Wolle in saurem Bade in sehr echten rothen Tönen an.10 kg of the i · 5-dianilidoanthraquinone are dissolved in 100 kg of oleum of 20 pCt. Entered anhydride content and stirred at 30 to 35 0 C. until a sample has become completely soluble in water. The melt is then poured into ice water, the solution is precisely neutralized with milk of lime, and the gypsum which has separated out is filtered off. The filtrate is reacted with sodium carbonate, the precipitated carbonate of lime is filtered off, and the sodium salt of sulfonic acid contained in the filtrate is obtained in dry form by evaporation. It forms a dark-colored powder, easily soluble in water with a yellowish-red color, which becomes more bluish with the addition of sodium hydroxide solution. The dye dissolves red in concentrated sulfuric acid, but is as good as insoluble in alcohol and aniline. He dyes wool in an acid bath in very genuine red tones.
In ganz analoger Weise lassen sich nach den oben gegebenen Beispielen die Condensationsproducte von ι · 5 - Di - ο - nitroanthrachinon mit anderen aromatischen Aminen in wasserlösliche Farbstoffe überführen; das Verfahren bleibt immer im Princip dasselbe und die erhältlichen Producte sind in ihren Eigenschaften einander sehr ähnlich.The condensation products can be found in a completely analogous manner according to the examples given above of ι · 5 - Di - ο - nitroanthraquinone with other aromatic amines in transfer water-soluble dyes; the procedure always remains the same in principle and the products available are very similar in their properties.
Selbstverständlich können an Stelle der aus reinem ι · 5-Dinitroanthrachinon und Aminen dargestellten Condensationsproducte auch diejenigen zur Verwendung kommen, welche aus rohem, durch Nitriren von Anthrachinon erhaltenen Nitroproduct dargestellt sind.Of course, instead of pure ι · 5-dinitroanthraquinone and amines Condensationsproducte shown also those come to use, which from crude nitro product obtained by nitriding of anthraquinone.
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DE108274C true DE108274C (en) |
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Country Status (1)
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- DE DENDAT108274D patent/DE108274C/de active Active
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