DE269215C - - Google Patents
Info
- Publication number
- DE269215C DE269215C DENDAT269215D DE269215DA DE269215C DE 269215 C DE269215 C DE 269215C DE NDAT269215 D DENDAT269215 D DE NDAT269215D DE 269215D A DE269215D A DE 269215DA DE 269215 C DE269215 C DE 269215C
- Authority
- DE
- Germany
- Prior art keywords
- brown
- yellow
- vat
- sulfuric acid
- solution
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000975 dye Substances 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 4
- 239000007859 condensation product Substances 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 239000000984 vat dye Substances 0.000 claims description 3
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 claims description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 claims 2
- 240000007817 Olea europaea Species 0.000 claims 1
- 241000490025 Schefflera digitata Species 0.000 claims 1
- 235000005811 Viola adunca Nutrition 0.000 claims 1
- 240000009038 Viola odorata Species 0.000 claims 1
- 235000013487 Viola odorata Nutrition 0.000 claims 1
- 235000002254 Viola papilionacea Nutrition 0.000 claims 1
- 238000004040 coloring Methods 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 235000015250 liver sausages Nutrition 0.000 claims 1
- 150000003142 primary aromatic amines Chemical class 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N N-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000000034 method Methods 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001043 yellow dye 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
- 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
- C09B5/2409—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 not provided for in one of the sub groups C09B5/26 - C09B5/62
- C09B5/2418—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 not provided for in one of the sub groups C09B5/26 - C09B5/62 only oxygen-containing hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
Vl 269215 KLASSE 22 δ. GRUPPEVl 269215 CLASS 22 δ. GROUP
R.WEDEKIND & CO. m. b. H. in UERDINGEN. Verfahren zur Darstellung echter Küpenfarbstoffe. Patentiert im Deutschen Reiche vom 19. Dezember 1912 ab.R.WEDEKIND & CO. m. b. H. in UERDINGEN. Process for the preparation of real vat dyes. Patented in the German Empire on December 19, 1912.
In dem Patent 265647 ist ein bromhaltiger gelber Küpenfarbstoff beschrieben worden, welcher durch Erhitzen von Dibrom-2-oxyanthrachinon auf Zusatz von Soda entsteht. Es hat sich nun herausgestellt, daß der Körper nicht nur ein ausgezeichneter Farbstoff an sich ist, sondern zugleich einen hervorragenden Farbstoffbildner darstellt. Der Körper ist imstande, mit Amincanthrachinonen wie überhaupt mit primären aromatischen Aminoverbindungen Kondensationsprodukte einzugehen. Es lagen keine Anhaltspunkte für das Verhalten der verwendeten Halogenderivate gegen aromatische Amine vor, es konnte, da die vorhandenen Halogenatome sich wahrscheinlich in ß-Stellung befinden, nicht vorausgesehen werden, ob überhaupt eine Reaktion eintreten würde, und welcher Art gegebenenfalls die Reaktionsprodukte sein würden. Die erhaltenen Produkte liefern aus alkalischer Küpe auf Baumwolle echte und feurige Färbungen; die Wasch-, Seifen-, Säure-, Chlor- und Lichtechtheit der Färbungen sind überraschend. Die Darstellung erfolgt durch Kondensation der Komponenten in Nitrobenzol oder Naphtalin auf Zusatz von Natriumacetat und Kupferpulver und Aufarbeiten der Schmelze in, üblicher Weise. Man kann z.B. nach dem Erkalten des Reaktionsgemisches den auskristallisierenden Anteil für sich abtrennen, aus dem Filtrat das Lösungsmittel mit Wasserdampf abdestillieren, dann den Rückstand mit Alkohol, Wasser, verdünnter Natronlauge, verdünnter Salzsäure waschen, oder man destilliert das Lösungsmittel direkt mit Wasserdampf ab und behandelt dann den Gesamtrückstand wie oben angegeben. Behufs Darstellung der Kondensationsprodukte ist die· Reinigung des gelben Farbstoffes durch Chloren nicht notwendig. Man geht am besten direkt vom getrockneten, alkaliunlöslichen Rohprodukt aus.In the patent 265647 a bromine-containing yellow vat dye has been described which by heating dibromo-2-oxyanthraquinone with the addition of soda. It has It has now been found that the body is not only an excellent dye in itself, but at the same time represents an excellent dye former. The body is able with amine canthraquinones as well as with primary aromatic amino compounds To enter condensation products. There was no evidence of the behavior of the used halogen derivatives against aromatic amines before, it could, since the existing ones Halogen atoms are probably in the ß-position, cannot be foreseen, whether a reaction would occur at all, and what kind of reaction products, if any would be. The products obtained are delivered from an alkaline vat Cotton real and fiery dyes; the washing, soap, acid, chlorine and light fastness the colorations are surprising. It is represented by condensation of the components in nitrobenzene or naphthalene on the addition of sodium acetate and copper powder and working up the melt in the usual way. For example, after the Cooling off the reaction mixture, separate the crystallizing portion for itself, from distill off the solvent with steam from the filtrate, then the residue with Wash alcohol, water, dilute sodium hydroxide solution, dilute hydrochloric acid, or you can distill the solvent is removed directly with steam and then the entire residue is treated as you can read above. For the purpose of representing the condensation products, the It is not necessary to clean the yellow dye with chlorine. It's best to go directly from the dried, alkali-insoluble crude product.
5,2 Teile bromhaltiges Küpengelb des Patents 265647, 4,5 Teile I-Aminoanthrachinon, 0,4 Teile Kupferpulver, 5 Teile entwässertes Natriumacetat werden in 100 Teilen Nitrobenzol während 5 bis 7 Stunden im Sieden erhalten. Nach dem Erkalten wird mit Al-: kohol versetzt, der ausgeschiedene Niederschlag abfiltriert, mit Alkohol und Wasser gewaschen und getrocknet. Dunkles, orangebraunes Pulver, unlöslich in Alkohol. Die Lösung in konzentrierter Schwefelsäure ist graublau, woraus Wasser orangebraune Flocken fällt.5.2 parts of bromine-containing vat yellow from patent 265647, 4.5 parts of I-aminoanthraquinone, 0.4 part of copper powder, 5 parts of dehydrated sodium acetate are obtained in 100 parts of nitrobenzene for 5 to 7 hours at the boil. After cooling with Al is: alcohol are added, the separated precipitate is filtered off, washed with alcohol and water and dried. Dark, orange-brown powder, insoluble in alcohol. The solution in concentrated sulfuric acid is gray-blue, from which orange-brown flakes fall into water.
5,2 Teile bromhaltiges Küpengelb des Patents 265647, 4,5 Teile 2-Aminoanthrachinon. Im übrigen wie_ bei Beispiel 1. Dunkelbraunes Pulver, unlöslich in Alkohol. Die Lösung in konzentrierter Schwefelsäure ist graurötlich, woraus Wasser dunkelbraune Flocken fällt.5.2 parts of bromine-containing vat yellow of patent 265647, 4.5 parts of 2-aminoanthraquinone. Otherwise as in Example 1. Dark brown powder, insoluble in alcohol. The solution in concentrated sulfuric acid is gray-reddish, from which water falls dark brown flakes.
65 Beispiel 3.65 Example 3.
5,2 Teile bromhaltiges Küpengelb des Patents 265647, 4,8 Teile 1 · 5-Diaminoanthrachinon. Im übrigen wie bei Beispiel 1. Braunrotes Pulver, unlöslich in Alkohol. Die Lö- 5.2 parts of bromine vat yellow of Patent 265647, 4.8 parts of 1 x 5-diaminoanthraquinone. Otherwise as in Example 1. Brown-red powder, insoluble in alcohol. The Lö-
Claims (1)
/ mit10 condensation product
/ with
SchwefelsäureSolution in conc.
sulfuric acid
I-Aminoanthrachinon
/2-Aminoanthrachinon
ι · 5-Diaminoanthrachinon
p-Toluidin / ■, ■
I-aminoanthraquinone
/ 2-aminoanthraquinone
ι · 5-diaminoanthraquinone
p-toluidine
braunviolett
blauviolett
braunviolettdark purple '
brown purple
blue-violet
brown purple
braun
braunrot
braunbrownish red
Brown
brownish red
Brown
gelbbraun
kupferrot
hellgelbolivbrown orange
yellow-brown
copper
light yellow olive
Publications (1)
Publication Number | Publication Date |
---|---|
DE269215C true DE269215C (en) |
Family
ID=526097
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT269215D Active DE269215C (en) |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE269215C (en) |
-
0
- DE DENDAT269215D patent/DE269215C/de active Active
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