DE151018C - - Google Patents
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- Publication number
- DE151018C DE151018C DENDAT151018D DE151018DA DE151018C DE 151018 C DE151018 C DE 151018C DE NDAT151018 D DENDAT151018 D DE NDAT151018D DE 151018D A DE151018D A DE 151018DA DE 151018 C DE151018 C DE 151018C
- Authority
- DE
- Germany
- Prior art keywords
- red
- same
- violet
- sulfonic acids
- water
- 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
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- 238000000034 method Methods 0.000 claims description 8
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- -1 sulfonic acids aromatic amines Chemical class 0.000 claims 1
- 239000000975 dye Substances 0.000 description 10
- FDDDEECHVMSUSB-UHFFFAOYSA-N Sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 6
- 150000003460 sulfonic acids Chemical class 0.000 description 6
- AXDJCCTWPBKUKL-UHFFFAOYSA-N 4-[(4-aminophenyl)-(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]aniline;hydron;chloride Chemical compound Cl.C1=CC(=N)C(C)=CC1=C(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 AXDJCCTWPBKUKL-UHFFFAOYSA-N 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- BBNQQADTFFCFGB-UHFFFAOYSA-N 1,2,4-Trihydroxyanthraquinone Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC(O)=C3C(=O)C2=C1 BBNQQADTFFCFGB-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- IVNZBWNBYXERPK-DZGBHZPSSA-K trisodium;(8Z)-7-oxo-8-[(4-sulfonatonaphthalen-1-yl)hydrazinylidene]naphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N\N=C3/C(=O)C=CC=4C=C(C=C(C=43)S([O-])(=O)=O)S(=O)(=O)[O-])=CC=C(S([O-])(=O)=O)C2=C1 IVNZBWNBYXERPK-DZGBHZPSSA-K 0.000 description 3
- 229960000583 Acetic Acid Drugs 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 240000000358 Viola adunca Species 0.000 description 2
- 235000005811 Viola adunca Nutrition 0.000 description 2
- 235000013487 Viola odorata Nutrition 0.000 description 2
- 235000002254 Viola papilionacea Nutrition 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N Boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- VKJKEPKFPUWCAS-UHFFFAOYSA-M Potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 1
- 240000002799 Prunus avium Species 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000001187 sodium carbonate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
JVI151018 KLASSE 226. JVI151018 CLASS 226.
In der Patentschrift 128753 ist gezeigt
worden, daß Sulfosäuren aromatischer Amine mit Halogenamidoanthrachinonderivaten unter
Bildung neuer, in der Regel sofort wasserlöslicher Farbstoffe reagieren. Diese Farbstoffbildung
ist nach den bisherigen Untersuchungen auf den Austausch von Halogen gegen Sulfoarylidoreste zurückzuführen.
Es hat sich nun gezeigt, daß Sulfosäuren aromatischer Amine befähigt sind, auch mit
Halogenoxyanthrachinonderivaten wertvolle Farbstoffe zu liefern, wobei gleichfalls ein
Austausch von Halogen gegen Sulfoarylidoreste erfolgt. Die Umsetzung vollzieht sichBeen in the patent 128 753 shown i st, that sulfonic acids of aromatic amines with Halogenamidoanthrachinonderivaten to form new, usually react immediately water-soluble dyes. According to previous investigations, this dye formation is due to the replacement of halogen by sulfoarylido radicals.
It has now been shown that sulfonic acids of aromatic amines are capable of supplying valuable dyes even with halooxyanthraquinone derivatives, with an exchange of halogen by sulfoarylido radicals also taking place. The implementation is taking place
15. auch hier schon beim Erhitzen in wäßriger Lösung.15. Even here already when heated in an aqueous solution.
Die nach dem Verfahren der vorliegenden Erfindung entstehenden Farbstoffe sind von den Produkten des Haupt-Patents 128753 insofern völlig verschieden, als sie infolge ihrer Darstellung aus hydroxylierten Anthrachinonderivaten Hydroxylgruppen enthalten, deren Anwesenheit von bestimmendem Einfluß auf den Farbstoffcharakter ist.The dyes resulting from the process of the present invention are from the products of the main patent 128753 are completely different in that they are as a result their preparation from hydroxylated anthraquinone derivatives contain hydroxyl groups, the presence of which has a determining influence on the character of the dye.
Von dem Verfahren der Patentschrift 114199 ist das vorliegende Verfahren dadurch unterschieden, daß die Kondensation zwischen dem Halogenoxyanthrachinonderivat und den Sulfosäuren aromatischer Amine, ohne daß die Zufügung von Kondensationsmitteln erforderlich wäre, sogar in wäßriger Lösung erfolgt. Außerdem ist das vorliegende Verfahren von den1 in den Patentschriften 114199 sowie , 127532 beschriebenen auch insofern verschieden , als bei letzteren unsulfierte Amine verwendet werden, so daß wasserunlösliche Earbkörper entstehen, während das nachstehend beanspruchte Verfahren infolge der Anwendung von Sulfosäuren aromatischer Amine direkt wasserlösliche, ohne weiteres zum Färben verwendbare Farbstoffsulfosäuren mit durch die Synthese bestimmbarer Stellung der Sulfogruppe liefert.The present process differs from the process of patent specification 114199 in that the condensation between the halooxyanthraquinone derivative and the sulfonic acids of aromatic amines even takes place in aqueous solution without the addition of condensation agents. In addition, the present process differs from the 1 described in patents 114199 and 127532 insofar as the latter uses unsulfated amines, so that water-insoluble bodies are formed, while the process claimed below, as a result of the use of sulfonic acids of aromatic amines, is directly water-soluble without provides further dye sulfonic acids which can be used for dyeing and whose position of the sulfo group can be determined by the synthesis.
Das Verfahren wird an folgenden Beispielen erläutert: 'The procedure is explained using the following examples: '
25 kg Monobrompurpurin (erhalten durch Bromieren von Purpurin in siedendem Eisessig mit der für die Bildung von Monobrompurpurin erforderlichen Menge Brom) werden mit 40 kg 85 prozentigem sulfanilsauren Natron und 100 1 Wasser so lange auf 2000C. im Autoklaven erhitzt, bis kein unverändertes Brompurpurin mehr nachzuweisen ist. Nach dem Erkalten hat sich das Reaktionsprodukt in Form einer bronzeglänzenden, kristallinischen Masse abgeschieden. Der Farbstoff wird abfiltriert, mit Kochsalzlösung gewaschen und getrocknet. Er wird vorteilhaft durch25 kg Monobrompurpurin (obtained by bromination of purpurin in boiling glacial acetic acid with the requisite for the formation of Monobrompurpurin amount of bromine) are mixed with 40 kg of 85-percentage sulfanilsauren soda and 100 1 water heated to 200 0 C. in an autoclave until no unchanged Brompurpurin more is to be proven. After cooling, the reaction product has deposited in the form of a bronze-shining, crystalline mass. The dye is filtered off, washed with sodium chloride solution and dried. He will be beneficial through
Lösen in konzentrierter Schwefelsäure und Fällen mit Wasser in Teigform gebracht (Eigenschäften s. Tabelle).Dissolve in concentrated sulfuric acid and precipitate into dough shape with water (For properties see table).
- Beispiel II.- Example II.
kg Chlorpurpurin (erhalten durch Chlorieren von in Salzsäure suspendiertem Purpurin mit der für die Bildung von Monochlorpupurin nötigen Menge chlorsauren Kalis) ίο werden mit 25 kg 85 prozentigem sulfanilsauren Natron und 50 1 Wasser im Auto-' klaven auf etwa 200° C. erhitzt und in gleicher Weise wie in Beispiel I weiterbehandelt (Eigenschaften s. Tabelle).kg of chloropurpurine (obtained by chlorinating purpurine suspended in hydrochloric acid with the amount of chlorate of potash necessary for the formation of monochlorpupurine) ίο with 25 kg of 85 percent sodium sulfanil and 50 liters of water in the car- ' Claves heated to about 200 ° C. and treated in the same way as in Example I. (Properties see table).
Beispiel III.Example III.
kg Chloralizarin (erhalten nach dem Verfahren der Patentschrift 77179) werden mit 30 kg 85 prozentigem sulfanilsauren Natron wie vorbeschrieben auf i8o° C. erhitzt. Der gebildete Farbstoff wird aufgearbeitet wie oben angegeben (Eigenschaften s. Tabelle).kg of chloralizarin (obtained by the process of patent specification 77179) heated to 180 ° C. with 30 kg of 85 percent sodium sulfanil as described above. The dye formed is worked up as indicated above (see table for properties).
15 kg Monobromchinizarin, 15 kg Borsäure, 30 kg 85 prozentiges sulfanilsaures Natron, 70 1 Wasser werden durch Erhitzen auf 2000C. in Farbstoff übergeführt (Eigenschaften s. Tabelle).15 kg Monobromchinizarin, 15 kg of boric acid, 30 kg of 85 owned sulfanilsaures soda, 70 1 of water by heating to 200 0 C. in dye transferred (s properties. Table).
In analoger Weise liefern andere Sulfosäuren aromatischer Amine bei der Kondensation mit Halogenoxyanthrachinonderivaten Farbstoffe von ähnlichen Eigenschaften wie die vorstehend beschriebenen.In an analogous manner, other sulfonic acids give aromatic amines on condensation with halogenoxyanthraquinone derivatives, dyes having properties similar to those described above.
Lösung in:Solution in:
Wasserwater
Natriumkarbonat Sodium carbonate
Natronlauge konz.
Schwefelsäure Caustic soda conc.
sulfuric acid
Borschwefel
säureBorosulfur
acid
EisessigGlacial acetic acid
Anilinaniline
70 Färbung.70 coloring.
aufon
chromgebeizter Wolle ·chrome-stained wool
Brompurpurin
SulfanilsalzBromopurpurine
Sulfanil salt
in der Wärme leicht löslich mit roter FarbeEasily soluble in heat with a red color
fuchsinrotfuchsin red
violett rotviolettviolet red-violet
blaublue
kirschrotcherry red
fuchsinrotfuchsin red
violettviolet
bisuntil
violettschwarz purple black
Brompurpurin +
metanilsaures NatronBromopurpurine +
metanilate of soda
desgl.the same
blaustichigrot bluish red
Brompurpurin -f- p-toluidinsulfosaures NatronBromopurpurine -f- p-toluidinsulfosaures Baking soda
desgl.the same
desgl.the same
desgl. desgl.the same.
fuchsinrotfuchsin red
blauviolett blue-violet
desgl.the same
wemrotwemrot
desadesa
desgl.the same
violettviolet
desgl.the same
fuchsinrotfuchsin red
desgl.the same
Chlorpurpurin (D. R. P.
77179) + SulfanilsalzChlorpurpurin (DRP
77179) + sulfanil salt
desgl.the same
fuchsinrotfuchsin red
desgl.the same
rotviolettred-violet
blaublue
desgl.the same
desgl.the same
desgl.the same
Chloralizarin +
SulfanilsalzChloralizarine +
Sulfanil salt
schwerheavy
löslichsoluble
braunrotbrownish red
rotviolett braunrotred-violet brown-red
violettviolet
braunrotbrownish red
rotbraunred-brown
trübe violettcloudy purple
BiOmchinizarin
SulfanilsalzBiOmchinizarin
Sulfanil salt
schwerheavy
löslichsoluble
violettrotpurple red
violettrotpurple red
blauviolett violettrotblue-violet violet-red
desgl.the same
rotRed
trübe violettrotcloudy purple-red
violettblau bis violet blue to
blauschwarz.. blue black ..
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE151018C true DE151018C (en) |
Family
ID=417872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT151018D Active DE151018C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE151018C (en) |
-
0
- DE DENDAT151018D patent/DE151018C/de active Active
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