DE906483C - Process for the production of chromium-containing dyes - Google Patents
Process for the production of chromium-containing dyesInfo
- Publication number
- DE906483C DE906483C DEF3565D DEF0003565D DE906483C DE 906483 C DE906483 C DE 906483C DE F3565 D DEF3565 D DE F3565D DE F0003565 D DEF0003565 D DE F0003565D DE 906483 C DE906483 C DE 906483C
- Authority
- DE
- Germany
- Prior art keywords
- chromium
- weight
- parts
- dyes
- production
- 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
Links
- 239000000975 dye Substances 0.000 title claims description 20
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims description 12
- 229910052804 chromium Inorganic materials 0.000 title claims description 12
- 239000011651 chromium Substances 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 229940018563 3-aminophenol Drugs 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001844 chromium Chemical class 0.000 description 2
- 150000001845 chromium compounds Chemical class 0.000 description 2
- 229910021563 chromium fluoride Inorganic materials 0.000 description 2
- QOWZHEWZFLTYQP-UHFFFAOYSA-K chromium(3+);triformate Chemical compound [Cr+3].[O-]C=O.[O-]C=O.[O-]C=O QOWZHEWZFLTYQP-UHFFFAOYSA-K 0.000 description 2
- GRWVQDDAKZFPFI-UHFFFAOYSA-H chromium(III) sulfate Chemical compound [Cr+3].[Cr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRWVQDDAKZFPFI-UHFFFAOYSA-H 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- 229910021555 Chromium Chloride Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 1
- WYYQVWLEPYFFLP-UHFFFAOYSA-K chromium(3+);triacetate Chemical compound [Cr+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WYYQVWLEPYFFLP-UHFFFAOYSA-K 0.000 description 1
- VBVRWWZABFQIAA-UHFFFAOYSA-H chromium(3+);trisulfite Chemical compound [Cr+3].[Cr+3].[O-]S([O-])=O.[O-]S([O-])=O.[O-]S([O-])=O VBVRWWZABFQIAA-UHFFFAOYSA-H 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- -1 perspiration Substances 0.000 description 1
- 239000013535 sea water 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
- C09B11/245—Phthaleins having both OH and amino substituent(s) on aryl ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung von chromhaltigen Farbstoffen Zusatz zum Patent 889 493 Gegenstand des Patents 889 4.97 ist ein Verfahren zur Herstellung von chromhaltigen Farbstoffen der Phthaleinreihe, das dadurch gekennzeichnet ist, daß man die nach dem Verfahren der Patentschrift 69270S erhältlichen Farbstoffe der Phthaleinreihe durch Behandlung mit chromabgebenden Mitteln in komplexe Chromverbindungen überführt.Process for the production of chromium-containing dyes Addition to the patent 889 493 The subject of the patent 889 4.97 is a process for the production of chromium-containing dyes of the phthalein series, which is characterized in that the dyes of the phthalein series obtainable by the process of patent 69270S are treated with chromium-releasing agents converted into complex chromium compounds.
Es wurde nun gefunden, daß man ebenfalls chromhaltige Farbstoffe von klaren Farbtönen und sehr guten- Echtheitseigenschaften erhält, wenn man die nach dem Verfahren der Patentschrift 720 167 erhältlichen Farbstoffe der Phthaleinreihe durch Behandlung mit chromabgebenden Mitteln in komplexe Chromverbindungen überführt.It has now been found that chromium-containing dyes of clear shades and very good fastness properties are obtained if the phthalein series dyes obtainable by the process of patent specification 720 167 are converted into complex chromium compounds by treatment with chromium-releasing agents.
Die neuen Chromkomplexverbindungen färben die Faser aus saurem Bade in sehr klaren gelbstichigbis blaustichigroten Farbtönen, die, ohne nachchromiert zu werden, sehr gute Echtheitseigenschaften besitzen.The new chromium complex compounds color the fibers from acid baths in very clear yellow-tinged to bluish-tinged red shades, without being chromed have very good fastness properties.
Die bei dem Verfahren zur Anwendung kommenden Ausgangsfarbstoffe sind erhältlich, wenn man i Mol i-Oxybenzol-2, q, 5-tricarbonsäure oder deren Anhydrid mit 2 Mol eines m-Aminophenols, das in para= Stellung zum Stickstoffatom ein reaktionsfähiges Kernwasserstoffatom enthält und dessen Stickstoffatom Bestandteil eines heterocyclischen Ringsystems ist, kondensiert oder wenn man i Mol einer i-Oxy-4-(4'-amino-6'-oxybenzoyl)-benzol 2, 5-dicarbonsäure oder i-Oxy-3-(4'-amino-6'-oxybenzoyl)-benzol-4, 6-dicärbonsäure, deren Stickstoffatome Bestandteile eines heterocyclischen Ringsystems sind, mit i 14Iol eines m-Aminophenols, dessen Stickstoffatom auch Bestandteil eines heterocyclischen Ringsystems sein kann, kondensiert.The starting dyes used in the process are obtainable if one mole of i-oxybenzene-2, q, 5-tricarboxylic acid or its anhydride with 2 mol of an m-aminophenol, which in para = position to the nitrogen atom is a reactive Contains nuclear hydrogen atom and its nitrogen atom is part of a heterocyclic Ring system is condensed or if one mole of an i-oxy-4- (4'-amino-6'-oxybenzoyl) -benzene 2, 5-dicarboxylic acid or i-oxy-3- (4'-amino-6'-oxybenzoyl) -benzene-4, 6-dicarboxylic acid, whose nitrogen atoms are components of a heterocyclic ring system, with i 14Iol of a m-aminophenol, the nitrogen atom of which is also part of a heterocyclic one Ring system can be condensed.
Als chromabgebende- Mittel, mit denen die oben beschriebenen Farbstoffe der Phthaleinreihe behandelt werden, können sowohl anorganische Chromsalze, wie Chromfluorid, Chromsulfat, Chromchlorid, Chromsulfit, als auch organische Chromsalze, z. B. Chromacetat oder Chromformiat, verwendet werden. Das Behandeln mit den chromabgebenden Mitteln 'kann in saurer, neutraler oder alkalischer Lösung mit geeigneten Zusätzen oder ohne weitere Zusätze in. offenen Gefäßen oder unter Druck erfolgen. Die nach dem vorliegenden Verfahren erhältlichen chromhaltigen Farbstoffe sind den aus der Patentschrift 123 o77 bekannten, in üblicher Weise chromierten Farbstoffen in ihren färberischen Eigenschaften, besonders in der Wasser-, Schweiß-, Seewasser- und Walkechtheit, überlegen: Beispiel i 5,7o Gewichtsteile des Natriumsalzes des Farbstoffes erhältlich nach dem Verfahren der Patentschrift 72o 167, Beispiel i, ioo Gewichtsteile Wasser und 58 Gewichtsteile o,97o/oige wäßrige Chromsulfatlösung werden 24 Stunden auf ioo° erhitzt. Der ausgefallene Farbstoff wird abgesaugt und mit Natriumhydroxyd in ein leicht lösliches Salz übergeführt. Die Lösung dieses Salzes wird eingedampft. Der Farbstoff liefert aus saurem Bad auf Wolle ein blaustichiges Rosa. Beispiel 2 5,38 Gewichtsteile des Natriumsalzes des Farbstoffes erhältlich nach dem Verfahren der Patentschrift 720 167, Beispiel 2, ioo Gewichtsteile Wasser und 21 Gewichtsteile2,85o/oigeChromformiatlösungwerden 24 Stunden auf ioo° erhitzt und, wie in Beispiel i beschrieben, aufgearbeitet. Der Farbstoff färbt Wolle aus schwefelsaurem Bade blaustichigrot an. Die Färbungen haben gute Echtheitseigenschaften. Beispiel 3 5,94 Gewichtsteile des Natriumsalzes des Farbstoffes erhältlich nach Patentschrift 72o 167, Beispiel 3, ioo Gewichtsteile Wasser und 58 Gewichtsteile 0,97o/oige Chromfluoridlösung werden 24 Stunden auf 15o° erhitzt. Nach dem Eindampfen ist der Rückstand (8,2 Gewichtsteile) nicht mehr völlig in Wasser löslich. Er wird deshalb mit 35 Gewichtsteilen normaler Natronlauge in ioo Gewichtsteilen Wasser in Lösung gebracht. Die Lösung wird nach etwaigem Filtrieren zur Trockne eingedampft. Der Farbstoff färbt die tierische Faser in blaustichigen Rosatönen von guten NaBechtheiten.As chromium-releasing agents with which the above-described dyes of the phthalein series are treated, both inorganic chromium salts such as chromium fluoride, chromium sulfate, chromium chloride, chromium sulfite, and organic chromium salts, e.g. B. chromium acetate or chromium formate can be used. The treatment with the chromium-releasing agents can be carried out in an acidic, neutral or alkaline solution with suitable additives or without further additives in open vessels or under pressure. The chromium-containing dyes obtainable by the present process are superior to the conventionally chromed dyes known from patent 123 077 in their coloring properties, especially in the fastness to water, perspiration, seawater and milled: Example i 5.7o parts by weight of the Sodium salt of the dye obtainable by the process of patent specification 72o 167, example i, 100 parts by weight of water and 58 parts by weight of o.97% aqueous chromium sulfate solution are heated to 100 ° for 24 hours. The precipitated dye is filtered off with suction and converted into a readily soluble salt with sodium hydroxide. The solution of this salt is evaporated. The dye produces a bluish pink on wool from an acidic bath. Example 2 5.38 parts by weight of the sodium salt of the dye obtainable by the process of patent specification 720 167, example 2, 100 parts by weight of water and 21 parts by weight of 2.850% chromium formate solution are heated to 100 ° for 24 hours and worked up as described in example i. The dye stains wool from sulfuric acid baths with a bluish tinge. The dyeings have good fastness properties. Example 3 5.94 parts by weight of the sodium salt of the dye obtainable according to patent specification 72o 167, example 3, 100 parts by weight of water and 58 parts by weight of 0.97% chromium fluoride solution are heated to 150 ° for 24 hours. After evaporation, the residue (8.2 parts by weight) is no longer completely soluble in water. It is therefore brought into solution with 35 parts by weight of normal sodium hydroxide solution in 100 parts by weight of water. After filtering if necessary, the solution is evaporated to dryness. The dye dyes the animal fibers in bluish pink tones with good wet fastness properties.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF3565D DE906483C (en) | 1936-10-17 | 1936-10-17 | Process for the production of chromium-containing dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF3565D DE906483C (en) | 1936-10-17 | 1936-10-17 | Process for the production of chromium-containing dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE906483C true DE906483C (en) | 1954-03-15 |
Family
ID=7083822
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF3565D Expired DE906483C (en) | 1936-10-17 | 1936-10-17 | Process for the production of chromium-containing dyes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE906483C (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE122352C (en) * | ||||
| DE123077C (en) * | ||||
| DE397331C (en) * | 1922-04-09 | 1924-06-24 | Basf Ag | Process for the preparation of water-soluble chromium compounds |
| DE441867C (en) * | 1925-08-06 | 1927-03-12 | I G Farbenindustrie Akt Ges | Process for the preparation of chromium-containing dyes |
-
1936
- 1936-10-17 DE DEF3565D patent/DE906483C/en not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE122352C (en) * | ||||
| DE123077C (en) * | ||||
| DE397331C (en) * | 1922-04-09 | 1924-06-24 | Basf Ag | Process for the preparation of water-soluble chromium compounds |
| DE441867C (en) * | 1925-08-06 | 1927-03-12 | I G Farbenindustrie Akt Ges | Process for the preparation of chromium-containing dyes |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE906483C (en) | Process for the production of chromium-containing dyes | |
| DE906484C (en) | Process for the production of chromium-containing dyes | |
| DE629732C (en) | Process for improving the waterfastness of colors | |
| DE889497C (en) | Process for the production of chromium-containing dyes | |
| DE2926184A1 (en) | NEW DISAZO DYES, THEIR PRODUCTION AND USE | |
| DE415534C (en) | Process for the preparation of polymethine dyes | |
| DE748824C (en) | Process for the production of acidic wool dyes | |
| DE654849C (en) | Process for the production of azo dyes | |
| DE638547C (en) | Process for the preparation of a copper-containing disazo dye | |
| DE663818C (en) | Process for the preparation of water-soluble compounds of heterocyclic compounds | |
| DE709632C (en) | Process for the preparation of nitro dyes | |
| DE741470C (en) | Process for the production of acidic wool dyes | |
| DE628961C (en) | Process for the preparation of monoazo dyes | |
| DE732971C (en) | Process for the production of chromable dyes of the phthalein series | |
| DE650557C (en) | Process for the production of water-insoluble azo dyes | |
| DE717501C (en) | Process for the preparation of unsymmetrical polymethine dyes | |
| DE656488C (en) | Process for the production of chromium-containing dyes | |
| DE745459C (en) | Process for the production of disazo and trisazo dyes | |
| DE738049C (en) | Process for the production of acidic dyes of the naphthophenosafranin series | |
| DE593572C (en) | Process for the production of gray dyes of the anthraquinone series | |
| DE467038C (en) | Process for dyeing artificial silk from acidyl celluloses, cellulose ethers and their conversion products | |
| DE676729C (en) | Process for the preparation of water-soluble monoazo dyes | |
| DE700757C (en) | en | |
| DE888902C (en) | Process for the preparation of acidic monoazo dyes | |
| DE731678C (en) | Process for the preparation of chromium-containing o-oxyazo dyes |