DE121684C - - Google Patents
Info
- Publication number
- DE121684C DE121684C DENDAT121684D DE121684DA DE121684C DE 121684 C DE121684 C DE 121684C DE NDAT121684 D DENDAT121684 D DE NDAT121684D DE 121684D A DE121684D A DE 121684DA DE 121684 C DE121684 C DE 121684C
- Authority
- DE
- Germany
- Prior art keywords
- diamidoanthraquinone
- crude
- blue
- acid
- tetrabromo
- 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
- 239000007859 condensation product Substances 0.000 claims description 7
- 150000003142 primary aromatic amines Chemical class 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
- 239000000975 dye Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 3
- 210000002268 Wool Anatomy 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000006011 modification reaction Methods 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- UPKAWFACSJWKND-ZXFFUEEESA-J tetrasodium;(6E)-4-amino-6-[[4-[4-[(2Z)-2-(8-amino-1-oxo-5,7-disulfonatonaphthalen-2-ylidene)hydrazinyl]-3-methoxyphenyl]-2-methoxyphenyl]hydrazinylidene]-5-oxonaphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C\1=CC2=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C(N)=C2C(=O)C/1=N/NC(C(OC)=C1)=CC=C1C1=CC=C(N\N=C\2C(C3=C(N)C(=CC(=C3C=C/2)S([O-])(=O)=O)S([O-])(=O)=O)=O)C(OC)=C1 UPKAWFACSJWKND-ZXFFUEEESA-J 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N Anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-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
- YSVBPNGJESBVRM-ZPZFBZIMSA-L Carmoisine Chemical compound [Na+].[Na+].C1=CC=C2C(/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)O)=CC=C(S([O-])(=O)=O)C2=C1 YSVBPNGJESBVRM-ZPZFBZIMSA-L 0.000 description 1
- 229940031019 Carmoisine Drugs 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N Chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 206010022000 Influenza Diseases 0.000 description 1
- 240000002799 Prunus avium Species 0.000 description 1
- 239000004176 azorubin Substances 0.000 description 1
- 235000012733 azorubine Nutrition 0.000 description 1
- ZSJHIZJESFFXAU-UHFFFAOYSA-N boric acid;phosphoric acid Chemical compound OB(O)O.OP(O)(O)=O ZSJHIZJESFFXAU-UHFFFAOYSA-N 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
- 150000001875 compounds Chemical class 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-N meta-phosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 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
- C09B1/34—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
¥η^γϊ- flu¥ η ^ γϊ- flu
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
Vr 121684 KLASSE 226.Vr 121684 CLASS 226.
Zusatz zum Patente 116546 vom ig. Oktober 1898.Addition to patents 116546 from ig. October 1898.
Patentirt im Deutschen Reiche vom 16. Dezember 1898 ab. Längste Dauer: 18. Oktober 1913.Patented in the German Empire on December 16, 1898. Longest duration: October 18, 1913.
In der Patentschrift 116546 ist die Darstellung von Sulfosäuren von Anthracenfarbstoffen beschrieben, welche erhalten werden durch Behandlung von Condensationsproducten aus halogensLibstituirten Dialphyldiamidoanthrachinonen und primären aromatischen Aminen mit sulfirenden Mitteln.In patent specification 116546 the illustration is of sulfonic acids of anthracene dyes, which are obtained by treating condensation products from halogen-substituted dialphyldiamidoanthraquinones and primary aromatic amines with sulphurizing agents.
Es wurde nun gefunden, dafs diese Condensationsproducte ersetzt werden können durch diejenigen, welche aus Tetrabromanthrachinon bezw. dem aus rohem 1 · 5 -Diamidoanthrachinon erhaltenen Tetrabromderivat durch Einwirkung von primären aromatischen Aminen nach dem Verfahren der Patentschrift 121528 darstellbar sind.It has now been found that these condensation products can be replaced by those, which respectively from tetrabromanthraquinone. that from crude 1 · 5 -diamidoanthraquinone obtained tetrabromo derivative by the action of primary aromatic amines after The method of patent specification 121528 can be represented are.
Die so erhaltenen Sulfosäuren färben sowohl chromgebeizte als auch ungeheizte Wolle meist in blauen bis grünblauen Tönen an; das Färben der ungeheizten Wolle in saurem Bade und nachträgliche Behandlung mit Metallbeizen liefert ähnliche Resultate.The sulfonic acids obtained in this way usually dye both chrome-stained and unheated wool in blue to green-blue tones; the dyeing of unheated wool in an acid bath and subsequent treatment with metal stains gives similar results.
Zur Darstellung dieser Farbstoffsulfosäuren werden die nach der Patentschrift 121528 erhältlichen rohen oder gereinigten Condensationsproducte aus Tetrabromdiamidoanthrachinonen und primären aromatischen Aminen mit den üblichen Sulfirungsmitteln, wie concentrirter Schwefelsäure, rauchender Schwefelsäure, Schwefelsäurechlorhydrin, Gemisch von Schwefelsäure und Borsäure oder Metaphosphorsäure, mit oder ohne Zusatz von Kieselguhr u. s. w. längere Zeit bei gewöhnlicher Temperatur oder kürzere Zeit bei höherer Temperatur behandelt.To represent these dye sulfonic acids are available according to the patent 121528 crude or purified condensation products from tetrabromodiamidoanthraquinones and primary aromatic amines with the usual sulphurizing agents, such as concentrated Sulfuric acid, fuming sulfuric acid, sulfuric acid chlorohydrin, mixture of Sulfuric acid and boric acid or metaphosphoric acid, with or without the addition of kieselguhr and so on for a longer time at normal temperature or for a shorter time at a higher temperature.
Zur Erläuterung des Verfahrens dienen folgende Beispiele:The following examples serve to explain the procedure:
io kg des nach Beispiel ι der Patentschrift 12i 528 erhaltenen Condensationsproductes aus Anilin undTetrabrom-1 · 5 - diamidoanthrachinon werden in 200 kg Schwefelsäure von 66° B. eingetragen und bei gewöhnlicher Temperatur so lange gerührt, bis eine Probe in heifsem Wasser löslich geworden ist. Hierauf wird die Schmelze in Wasser gegossen, wobei sich die in verdünnter Säure ziemlich schwer lösliche Sulfosäure zum grofsen Theil abscheidet; sie wird durch Zusatz von Kochsalz oder Chlorkalium vollständig gefällt, abfiltrirt und getrocknet (Eigenschaften siehe Tabelle).io kg of the example of the patent 12i 528 obtained condensation products Aniline and tetrabromo-1 · 5 - diamidoanthraquinone are dissolved in 200 kg sulfuric acid of 66 ° B. entered and stirred at ordinary temperature until a sample is in hot Water has become soluble. Then the melt is poured into water, whereby the sulfonic acid, which is rather sparingly soluble in dilute acid, is largely separated out; it is completely precipitated by the addition of table salt or potassium chloride, filtered off and dried (see table for properties).
Statt des vorbesprochenen, aus dem Tetrabromderivat des reinen 1-5 - Diamidoanthrachinons und Anilin erhaltenen Condensationsproductes kann auch dasjenige verwendet werden, welches aus dem rohen Tetrabromderivat' des rohen 1· 5-Diamidoanthrachinons (welches bekanntlich aufser der 1 · 5 -Verbindung Isomere derselben enthält) und Anilin entsteht.Instead of the previously discussed, from the tetrabromo derivative of the pure 1-5 - diamidoanthraquinone and aniline-obtained condensation products can also be used which is made from the crude tetrabromo derivative of the crude 1 · 5-diamidoanthraquinone (which as is known, apart from the 1 × 5 compound, it contains isomers of the same) and aniline is formed.
In gleicher Weise verfährt man, wenn statt des Anilins das o- oder p-Toluidinconden-The same procedure is followed if, instead of the aniline, the o- or p-toluidine condene
sationsproduct des Tetrabromdiamidoanthrachinons verwendet wird.sationsproduct of the tetrabromodiamidoanthraquinone is used.
ίο kg des nach der Patentschrift 121528 aus Tetrabromdiainidoanthrachinon und ß-Naphtylamin erhaltenen Condensationsproductes werden in 200 kg Schwefelsäure von 660B. eingetragen und bis zur Wasserlöslichkeit auf 60 bis 70° C. erwärmt. Durch Eingiefsen in Wasser und Aussalzen mit Kochsalz oder Chlorkalium wird die leicht lösliche Sulfosä'ure abgeschieden (Eigenschaften siehe Tabelle).ίο kg of Condensationsproductes obtained according to the patent specification 121528 from Tetrabromdiainidoanthrachinon and beta-naphthylamine are added to 200 kg of sulfuric acid of 66 0 B. and heated up to the water to 60 to 70 ° C. The easily soluble sulfonic acid is separated out by pouring it into water and salting out with common salt or potassium chloride (see table for properties).
In gleicher Weise verfährt man, wenn statt des /3-Naphtylamin- das a-Naphtylamincondensatiorisproduct zur Anwendung gelangt.The same procedure is followed if, instead of the / 3-naphthylamine, the α-naphthylamine condensation product is used is applied.
Die Eigenschaften der nach vorstehenden Beispielen erhaltenen Farbstoffe sind aus nachstehender Tabelle ersichtlich.The properties of the dyes obtained in the above examples are as follows Table.
des
Condensations
productes aus
Tetrabromdiamido-
anthrachinon undSulfonic acid
of
Condensations
productes from
Tetrabromodiamido
anthraquinone and
trocknen
FarbstoffsAppearance of the
dry
Dye
66° B.sulfuric acid
66 ° B.
ungeheizter
Wolle in
saurem BadeColoring on
unheated
Wool in
acid bath
reinblauer Farbeeasily soluble with
pure blue color
änderungno colors
modification
trübblauer Farbeeasily soluble with
cloudy blue color
blausomewhat greenish
blue
Pulverbluish gray
powder
grünblaueasily soluble
green Blue
Pulvergray-black
powder
blauer Farbeeasily soluble with
blue color
grünerbecomes something
greener
Pulverblackish
powder
blaustichig grüner
Farbeeasily soluble with
bluish green
colour
änderungno colors
modification
Claims (1)
Publications (1)
Publication Number | Publication Date |
---|---|
DE121684C true DE121684C (en) |
Family
ID=390660
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT121684D Active DE121684C (en) |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE121684C (en) |
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0
- DE DENDAT121684D patent/DE121684C/de active Active
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