DE178130C - - Google Patents
Info
- Publication number
- DE178130C DE178130C DE1905178130D DE178130DA DE178130C DE 178130 C DE178130 C DE 178130C DE 1905178130 D DE1905178130 D DE 1905178130D DE 178130D A DE178130D A DE 178130DA DE 178130 C DE178130 C DE 178130C
- Authority
- DE
- Germany
- Prior art keywords
- blue
- diaminoanthraquinone
- green
- alizarin
- 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.)
- Expired - Lifetime
Links
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 claims description 10
- 239000000975 dye Substances 0.000 claims description 4
- 150000001454 anthracenes Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 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 6
- KGBXLFKZBHKPEV-UHFFFAOYSA-N Boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 6
- 239000004327 boric acid Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 240000007817 Olea europaea Species 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- XZSUEVFAMOKROK-UHFFFAOYSA-N 1,2-dihydroxy-3-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C(O)C([N+]([O-])=O)=C2 XZSUEVFAMOKROK-UHFFFAOYSA-N 0.000 description 2
- UHOKSCJSTAHBSO-UHFFFAOYSA-N Indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- JROURLWMOZCGJV-UHFFFAOYSA-N alizarin blue Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C1=CC=CN=C1C(O)=C2O JROURLWMOZCGJV-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000003638 reducing agent 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
- 150000004345 1,2-dihydroxyanthraquinones Chemical class 0.000 description 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N Anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
- 241000974482 Aricia saepiolus Species 0.000 description 1
- 241000131971 Bradyrhizobiaceae Species 0.000 description 1
- VBHKTXLEJZIDJF-UHFFFAOYSA-N Quinalizarin Chemical compound C1=CC(O)=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1O VBHKTXLEJZIDJF-UHFFFAOYSA-N 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- TZIQWQARHPGHIG-UHFFFAOYSA-N anthrarobin Chemical compound C1=CC=CC2=CC3=C(O)C(O)=CC=C3C(O)=C21 TZIQWQARHPGHIG-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 235000019239 indanthrene blue RS Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000004043 responsiveness Effects 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
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/44—Azines of the anthracene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
iNvjc'nr;! IH boc iNvjc'nr ;! IH boc
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- Ja 178130-— KLASSE 22 b. GRUPPE - Yes 178130-— CLASS 22 b. GROUP
Kondensationen von Oxyanthrachinonen mit Aminoanthrachinonen sind bisher nicht bekannt geworden. Es war auch von vornherein nicht zu erwarten, daß ein Zusammentritt von 5 Oxyanthrachinonen mit Aminoanthrachinonen unter Abspaltung von Wasser stattfinden würde, da die Aminoanthrachinone bekanntlich eine erheblich geringere Basizität besitzenCondensations of oxyanthraquinones with aminoanthraquinones are not yet known become. It was not to be expected from the outset that a meeting of 5 oxyanthraquinones with aminoanthraquinones take place with elimination of water would, since the aminoanthraquinones are known to have a considerably lower basicity
COCO
als die Amine der Benzol- und Naphtalinreihe und deshalb eine bei weitem geringere Reaktionsfähigkeit aufweisen.than the amines of the benzene and naphthalene series and therefore a far smaller one Have responsiveness.
Wir haben nun gefunden, daß sich Orthodiaminoanthrachinone (1 · 2- bezw. 2-3-Diaminoanthrachinon) mit Alizarin bezw. dessen Derivaten kondensieren unter Bildung von Farbstoffen der Indsnthrenreihe, z. B.We have now found that Orthodiaminoanthraquinones (1 · 2- or 2-3-diaminoanthraquinone) with alizarin resp. its derivatives condense to form Dyes of the Indsnthren range, e.g. B.
COCO
COCO
CO OH + H2N )0HCO OH + H 2 N) OH
2H2O.2H 2 O.
NHNH
COCO
Beispiel I.Example I.
20 kg Alizarin werden mit 20 kg ι · 2-Diaminoanthrachinon, 20 kg Borsäure und 200 kg Phenol 16 bis 20 Stunden zum Sieden erhitzt. -Man gießt nach dem Erkalten in heißes Wasser, filtriert ab und wäscht mit heißem Wasser aus. Zur Reinigung wird das Produkt mit siedenden organischen Lösungsmitteln, wie Pyridin, Nitrobenzol usw., extrahiert. Das Produkt ist höchst wahrscheinlich isomer mit dem Indanthren des Handels.20 kg of alizarin are mixed with 20 kg of ι · 2-diaminoanthraquinone, Boil 20 kg boric acid and 200 kg phenol for 16 to 20 hours heated. After cooling, you pour into hot water, filter off and wash with hot water. The product is cleaned with boiling organic solvents such as pyridine, nitrobenzene, etc. extracted. The product is most likely isomeric with the commercial indanthrene.
20 kg Purpurin werden mit 200 kg RoIikresol, 20 kg 1 · 2-Diäminoanthrachinon und20 kg of purpurin with 200 kg of RoIikresol, 20 kg of 1 · 2-dieminoanthraquinone and
COCO
20 kg Borsäure 6 bis 10 Stunden zum Sieden erhitzt. Man gießt nach dem Erkalten in heißes Wasser, filtriert und wäscht mit heißem Wasser aus. Zwecks Reinigung wird das Produkt getrocknet und mit heißen organischen Solventien ausgekocht. Das so erhaltene Oxyindanthren löst sich in konzentrierter Schwefelsäure olivgrün, es liefert mit Reduktionsmitteln eine blaue Küpe und färbt ungeheizte Baumwolle in grünlichblauen Tönen an. .20 kg of boric acid heated to boiling for 6 to 10 hours. One pours after cooling in hot water, filtered and washed off with hot water. Purpose of cleaning is the product dried and boiled with hot organic solvents. The oxyindanthrene thus obtained dissolves in concentrated Sulfuric acid olive green, with reducing agents it provides a blue vat and dyes unheated cotton greenish-blue Tones on. .
Man erhitzt ein Gemisch von 200 kg Phenol, 22 kg Alizarinblau, 20 kg 2-3-Diaminoanthrachinon und 20 kg Borsäure 6 bis 10 Stunden zum Sieden. Nach dem ErkaltenA mixture of 200 kg of phenol, 22 kg of alizarin blue, 20 kg of 2-3-diaminoanthraquinone is heated and 20 kg of boric acid to boil for 6 to 10 hours. After cooling down
gießt man in heißes Wasser, filtriert und zieht den Rückstand mit heißen organischen Solventien aus. Das so erhaltene Produkt löst sich in konzentrierter Schwefelsäure grün, ist sehr schwer löslich in organischen Solventien und bildet mit Reduktionsmitteln eine braune Küpe, aus der Baumwolle in grünen Tönen angefärbt wird.It is poured into hot water, filtered and the residue is drawn off with hot organic solvents the end. The product thus obtained dissolves in concentrated sulfuric acid, is green very sparingly soluble in organic solvents and forms a brown color with reducing agents Vat from which cotton is dyed in green tones.
17 kg Purpurin-α-sulfosäure (Anilinsalz) werden mit 10 kg 2 · 3-Diaminoanthrachinon, ίο kg Borsäure und 200 kg Phenol Unter kräftigem Rühren zum Sieden erhitzt, bis die Schmelze eine . intensiv blaue Farbe angenommen hat. Man läßt nun auf 8o° abkühlen und verdünnt die Schmelze mit 200 1 Alkohol, worauf die gebildete Oxyindanthrensulfosäure, die in Form eines blauen Nieder-Schlages abgeschieden ist, leicht durch Absaugen gewonnen werden kann. Das Produkt färbt Wolle blau.17 kg of purpurine-α-sulfonic acid (aniline salt) are with 10 kg 2 · 3-diaminoanthraquinone, ίο kg boric acid and 200 kg phenol sub vigorous stirring heated to the boil until the melt has a. assumed intense blue color Has. It is now allowed to cool to 80 ° and the melt is diluted with 200 liters of alcohol, whereupon the oxyindanthrene sulfonic acid formed, which is deposited in the form of a blue precipitate, easily by suction can be won. The product dyes wool blue.
10 kg 2 · 3-Diaminoanthrachinon, 11 kg ß-Nitroalizarin, 10 kg Borsäure und 120 kg Phenol werden im geschlossenen Gefäß 24 Stunden auf 200 bis 2200 erhitzt. Nach dem Erkalten rührt man das Ganze mit" heißem Wasser an, kocht auf' und filtriert. Durch Ausziehen des Rückstandes mit organischen Solventien werden die Verunreinigungen entfernt. 10 kg 2 · 3-diaminoanthraquinone, 11 kg ß-Nitroalizarin, 10 kg of boric acid and 120 kg of phenol are heated in the closed vessel 24 hours on 200 to 220 0th After cooling, the whole thing is stirred up with hot water, boiled up and filtered. The impurities are removed by exhausting the residue with organic solvents.
aus:Condensation product
the end:
konz.
SchwefelsäureSolution in
conc.
sulfuric acid
in
Ghinolinsolution
in
Ghinolin
alkalischem
HydrosulfitSolution in
alkaline
Hydrosulfite
auf
Baumwollecoloring
on
cotton
und Alizarinι · 2-diaminoanthraquinone
and alizarin
und Purpurinι · 2-diaminoanthraquinone
and purpurin
Purpurin-ct-sulfosäureι · 2-diaminoanthraquinone and
Purpurine-ct-sulfonic acid
blauhardly soluble
blue
und Alizarin2 · 3-diaminoanthraquinone
and alizarin
und ß-Nitroalizarin2 · 3-diaminoanthraquinone
and ß-nitroalizarin
und Alizarinblau2 · 3-diaminoanthraquinone
and alizarin blue
und Purpurin2 · 3-diaminoanthraquinone
and purpurin
Purpurin-a-sulfosäure2 · 3-diaminoanthraquinone and
Purpurin-a-sulfonic acid
und Alizarinbordeaux.2 · 3-diaminoanthraquinone
and alizarin bordeaux
6 kg Leukoalizarinbordeaux werden mit 5 kg 2 · 3-Diaminoanthrachinon, 5 g kristallisierter Borsäure und 80 kg Phenol 24 Stunden lang auf 200° erhitzt. Man gießt die Schmelze nach dem Erkalten in heißes Wasser, filtriert und zieht den getrockneten Rückstand mit organischen Solventien aus. Der unlösliche Teil besteht aus dem reinen Kondensationsprodukt, dessen Eigenschaften in der Tabelle aufgeführt sind.6 kg of leucoalizarin bordeaux are crystallized with 5 kg of 2x3-diaminoanthraquinone, 5 g Boric acid and 80 kg phenol heated to 200 ° for 24 hours. The melt is poured after cooling in hot water, filtered and pulls the dried residue with it organic solvents. The insoluble part consists of the pure condensation product, whose properties are listed in the table.
Ganz analog verläuft die Reaktion mit anderen Derivaten des Alizarins oder anderen o-Diaminoanthrachinonen.The reaction with other derivatives of alizarin or others proceeds in a completely analogous manner o-diaminoanthraquinones.
Die Eigenschaften einiger so dargestellten Indanthrenderivate sind in folgender Tabelle zusammengestellt.The properties of some of the indanthrene derivatives shown in this way are shown in the table below compiled.
Claims (1)
Verfahren zur Herstellung von KüpenPatent claim:
Method of making vats
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT29055D AT29055B (en) | 1905-10-23 | 1906-10-13 | Process for the preparation of vat dyes of the anthracene series. |
Publications (1)
Publication Number | Publication Date |
---|---|
DE178130C true DE178130C (en) |
Family
ID=442554
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE1905178130D Expired - Lifetime DE178130C (en) | 1905-10-23 | 1905-10-23 |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE178130C (en) |
-
1905
- 1905-10-23 DE DE1905178130D patent/DE178130C/de not_active Expired - Lifetime
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