CH273299A - Process for the preparation of a metal-containing monoazo dye. - Google Patents
Process for the preparation of a metal-containing monoazo dye.Info
- Publication number
- CH273299A CH273299A CH273299DA CH273299A CH 273299 A CH273299 A CH 273299A CH 273299D A CH273299D A CH 273299DA CH 273299 A CH273299 A CH 273299A
- Authority
- CH
- Switzerland
- Prior art keywords
- chromium
- dye
- monoazo dye
- metal
- monoazo
- Prior art date
Links
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D30/00—Producing pneumatic or solid tyres or parts thereof
- B29D30/06—Pneumatic tyres or parts thereof (e.g. produced by casting, moulding, compression moulding, injection moulding, centrifugal casting)
- B29D30/52—Unvulcanised treads, e.g. on used tyres; Retreading
-
- 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/01—Complex metal compounds of azo dyes characterised by the method of metallisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paper (AREA)
Description
Verfahren zur Herstellung eines metallhaltigen Monoazofarbstoffes. Es wurde gefunden, dass man zu einem wertvollen metallhaltigen Monoazofarbstoff nelangt, wenn man auf einen #vIonoazofarb- stoff der Formel
EMI0001.0006
unter Bedingungen, bei denen eine Abspal tung der Alkylgruppe des in o-Stellung zur Azogruppe befindlichen -0-Alkyl-Restes statt findet, chromabgebende Mittel einwirken lässt.
Der neue metallhaltige Farbstoff. ist eine dunkelgefärbte Substanz, welche sich in ver dünnter Natriumcarbonatlösung mit violetter und in konz. Schwefelsäure mit blauer Farbe löst und Wolle aus schwefelsaurem Bade in gleichmässigen, echten rotblauen Tönen färbt. .
Die beim vorliegenden Verfahren als Aus- gangSstoffe dienenden, der obigen Formel ent sprechenden Monoazofarbstoffe können herge stellt werden, indem man eine dianotierte 2-Alkoxy-5 -methoxy-l-aminobenzol-4-sulfon- sä.ure mit 2-Oxynaphthalin kuppelt.
Die in '.-'-Stellung der Diazokomponente befindliche Alkoxygruppe enthält vorzugsweise nur we nige, beispielsweise 1 bis 4 Kohlenstoffatome. Als besonders zweckmässiger Ausgangsstoff Für das vorliegende Verfahren erweist sich der aus dianotierter 2,5-Dimethoxy-l-amino- benzol-4-sulfonsäure erhältliche Monoazofarb- stoff.
Die Dianotierung der 2-Alkoxy-5-methoxy- 1-aminobenzol-4-sulfonsäure kann in üblicher, an sieh bekannter Weise, z. B. mit Hilfe von hatriumnitrit und Salzsäure erfolgen. Die Kupplung der Diazoverbindung mit 2-Oxy- naphthalin erfolgt zweckmässig in alkalischem Medium. Gegebenenfalls kann die Kupplung auch in Anwesenheit geeigneter Lösungs mittel, wie Alkohol oder Pyridin durchgeführt werden.
Die beim vorliegenden Verfahren als Aus gangsstoffe dienenden Monoazofarbstoffe kön nen gewünschtenfalls aus dem Kupplungs gemisch isoliert und von Verunreinigungen befreit werden. Im allgemeinen kann jedoch zur Behandlung mit. den chromabgebenden Mitteln die Kupplungsmasse als Ganzes und ohne Zwischenabscheidung verwendet werden. In der Regel ist es hierbei notwendig, das Kupplungsgemisch vor der Durchführung der Reaktion mit dem chromabgebenden Mittel auf den für diese Reaktion günstigen pli- Wert, d. ' h. auf schwach mineralsaure Reak tion einzustellen.
Als chromabgebende Mittel kommen beim vorliegenden Verfahren vor allem die Salze des dreiwertigen Chroms, wie Chromfluorid, Chromsulfate, Chromacetat und Chromfor- miat in Betracht. Die Behandlung mit den chromabgebenden Mitteln erfolgt unter sol chen Bedingungen, bei welchen eine Abspal tung der Alkylgruppe des in o-Stellung zur Azogruppe befindlichen -0-Alkyl-Restes statt findet.
Diese Abspaltung unter gleichzeitiger Bildung der komplexen Chromverbindung lässt sich nach an sich bekannter Methode durchführen, indem man die Behandlung mit dem chromabgebenden Mittel, z. B. mit Chromformiat oder Chromsulfat in wässrigem, vorzugsweise mineralsaiuem Medium unter Druck bei erhöhter Temperatur, z. B. Tem peratur zwischen 110 und 140 vornimmt.
<I>Beispiel:</I> 23,3 Teile 2,5-Dimethoxy-l-aminobenzol- 4-sulfonsäure werden in üblicher Weise in Ge genwart von. 19 Teilen 30 higer Salzsäure mit 7 Teilen Natriumnitrit diazotiert. Die Diazo- lösung wird unter Rühren zu einer auf 15 ge kühlten Lösung von 15 Teilen 2-Oxynaph- thalin,
16 Teilen einer 30 o/oigen Natritun- hydroxydlösung und 20 Teilen wasserfreiem Natriumcarbonat in 400 Teilen Wasser zu fliessen gelassen. Der entstandene Farbstoff fällt zum grössten Teil aus und wird abfil- tHert. Er stellt getrocknet eine dunkelrote Substanz dar, die sich in verdünnter Na triumearbonatlösung mit roter und in konz. Schwefelsäure mit rotblauer Farbe löst und \Volle aus saurem Bade in roten Tönen färbt.
Dieser Farbstoff kann ohne vorherige Trocknung in -die komplexe Chromverbindung übergeführt werden. Zu diesem Zweck wird die nach obigen Angaben erhaltene Farbstoff paste mit 1000 Teilen heissem Wasser ver rührt und 10 /oige Schwefelsäure bis zur schwach mineralsauren Reaktion zugegeben.
Nach Zugabe einer 5,7 Teile Cr enthaltenden Menge Chromsulfat [Cr=(S04)3] erhitzt man das Reaktionsgemisch im verbleiten Rührauto- klaven auf 125 bis 135 und rührt während 25 Stunden bei dieser Temperatur. Die filtrierte Chromierlösung wird mit verdünnter Na- triumhydroxydlösuing bis zur lackmusneu- tralen Reaktion versetzt und im Vakuum zur Trockne verdampft.
Process for the preparation of a metal-containing monoazo dye. It has been found that a valuable metal-containing monoazo dye is obtained if one uses a #vionoazo dye of the formula
EMI0001.0006
chromium-donating agents can act under conditions in which the alkyl group of the -0-alkyl radical in the o-position to the azo group is split off.
The new metal-containing dye. is a dark-colored substance, which in dilute sodium carbonate solution with violet and in conc. Sulfuric acid dissolves with a blue color and dyes wool from sulfuric acid bath in even, genuine red-blue tones. .
The monoazo dyes which serve as starting materials in the present process and correspond to the above formula can be prepared by coupling a dianotated 2-alkoxy-5-methoxy-1-aminobenzene-4-sulfonic acid with 2-oxynaphthalene.
The alkoxy group in the '. -' position of the diazo component preferably contains only a few, for example 1 to 4, carbon atoms. The monoazo dye obtainable from dianotated 2,5-dimethoxy-1-aminobenzene-4-sulfonic acid has proven to be a particularly suitable starting material for the present process.
The dianotation of 2-alkoxy-5-methoxy-1-aminobenzene-4-sulfonic acid can be carried out in a conventional manner known per se, e.g. B. with the help of hatrium nitrite and hydrochloric acid. The coupling of the diazo compound with 2-oxynaphthalene is expediently carried out in an alkaline medium. If necessary, the coupling can also be carried out in the presence of suitable solvents, such as alcohol or pyridine.
The monoazo dyes used as starting materials in the present process can, if desired, be isolated from the coupling mixture and freed from impurities. In general, however, can be used to treat with. the chromium-releasing agents, the coupling compound can be used as a whole and without intermediate deposition. As a rule, it is necessary here to bring the coupling mixture to the pli value that is favorable for this reaction, ie. ' H. adjust to weak mineral acid reaction.
Particularly suitable chromium-releasing agents in the present process are the salts of trivalent chromium, such as chromium fluoride, chromium sulfates, chromium acetate and chromium formate. The treatment with the chromium-releasing agents is carried out under such conditions in which the alkyl group of the -0-alkyl radical in the o-position to the azo group is split off.
This splitting off with simultaneous formation of the complex chromium compound can be carried out according to a method known per se by treating with the chromium-releasing agent, e.g. B. with chromium formate or chromium sulfate in aqueous, preferably mineralsaiuem medium under pressure at elevated temperature, for. B. Tem temperature between 110 and 140 makes.
<I> Example: </I> 23.3 parts of 2,5-dimethoxy-l-aminobenzene-4-sulfonic acid are in the usual manner in the presence of. 19 parts of 30 higer hydrochloric acid are diazotized with 7 parts of sodium nitrite. The diazo solution is stirred into a solution, cooled to 15, of 15 parts of 2-oxynaphthalene,
16 parts of a 30% sodium hydroxide solution and 20 parts of anhydrous sodium carbonate in 400 parts of water are allowed to flow. Most of the resulting dye precipitates and is filtered off. It is dried a dark red substance, which is in dilute sodium carbonate solution with red and in conc. Sulfuric acid dissolves with a red-blue color and colors full from acid baths in red tones.
This dye can be converted into the complex chromium compound without prior drying. For this purpose, the dye paste obtained according to the above information is stirred with 1000 parts of hot water and 10% sulfuric acid is added until the reaction has a weak mineral acidity.
After adding an amount of chromium sulfate [Cr = (S04) 3] containing 5.7 parts of Cr, the reaction mixture is heated to 125 to 135 in the leaded stirred autoclave and stirred at this temperature for 25 hours. The filtered chromating solution is mixed with dilute sodium hydroxide solution until a litmus-neutral reaction is obtained and evaporated to dryness in vacuo.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH273298T | 1948-02-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH273299A true CH273299A (en) | 1951-01-31 |
Family
ID=25731441
Family Applications (10)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH273299D CH273299A (en) | 1948-02-26 | 1948-02-26 | Process for the preparation of a metal-containing monoazo dye. |
CH273302D CH273302A (en) | 1948-02-26 | 1948-02-26 | Process for the preparation of a metal-containing monoazo dye. |
CH273305D CH273305A (en) | 1948-02-26 | 1948-02-26 | Process for the preparation of a metal-containing monoazo dye. |
CH273303D CH273303A (en) | 1948-02-26 | 1948-02-26 | Process for the preparation of a metal-containing monoazo dye. |
CH273298D CH273298A (en) | 1948-02-26 | 1948-02-26 | Process for the preparation of a metal-containing monoazo dye. |
CH273297D CH273297A (en) | 1948-02-26 | 1948-02-26 | Process for the preparation of a metal-containing monoazo dye. |
CH273301D CH273301A (en) | 1948-02-26 | 1948-02-26 | Process for the preparation of a metal-containing monoazo dye. |
CH270540D CH270540A (en) | 1948-02-26 | 1948-02-26 | Process for the preparation of a metal-containing monoazo dye. |
CH273300D CH273300A (en) | 1948-02-26 | 1948-02-26 | Process for the preparation of a metal-containing monoazo dye. |
CH274425D CH274425A (en) | 1948-02-26 | 1948-12-24 | Process for the preparation of a metal-containing monoazo dye. |
Family Applications After (9)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH273302D CH273302A (en) | 1948-02-26 | 1948-02-26 | Process for the preparation of a metal-containing monoazo dye. |
CH273305D CH273305A (en) | 1948-02-26 | 1948-02-26 | Process for the preparation of a metal-containing monoazo dye. |
CH273303D CH273303A (en) | 1948-02-26 | 1948-02-26 | Process for the preparation of a metal-containing monoazo dye. |
CH273298D CH273298A (en) | 1948-02-26 | 1948-02-26 | Process for the preparation of a metal-containing monoazo dye. |
CH273297D CH273297A (en) | 1948-02-26 | 1948-02-26 | Process for the preparation of a metal-containing monoazo dye. |
CH273301D CH273301A (en) | 1948-02-26 | 1948-02-26 | Process for the preparation of a metal-containing monoazo dye. |
CH270540D CH270540A (en) | 1948-02-26 | 1948-02-26 | Process for the preparation of a metal-containing monoazo dye. |
CH273300D CH273300A (en) | 1948-02-26 | 1948-02-26 | Process for the preparation of a metal-containing monoazo dye. |
CH274425D CH274425A (en) | 1948-02-26 | 1948-12-24 | Process for the preparation of a metal-containing monoazo dye. |
Country Status (5)
Country | Link |
---|---|
AT (1) | AT166451B (en) |
CH (10) | CH273299A (en) |
DE (1) | DE848979C (en) |
DK (1) | DK74309C (en) |
NL (1) | NL69348C (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2599147A (en) * | 1948-02-26 | 1952-06-03 | Ciba Ltd | Chromiferous monoazo-dyestuffs |
DE1016866B (en) * | 1955-04-01 | 1957-10-03 | Basf Ag | Process for the preparation of chromium-containing o, o'-dioxyazo dyes |
DE2855970A1 (en) * | 1978-12-23 | 1980-07-10 | Hoechst Ag | METHOD FOR PRODUCING 2,5-DIALKOXY-ANILINE-4-SULPHONIC ACIDS |
CN107345081A (en) * | 2017-07-24 | 2017-11-14 | 北京泛博清洁技术研究院有限公司 | Fur recyclable dyeing phloxine compound and its synthesis and application process |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE474997C (en) * | 1926-08-29 | 1929-04-15 | I G Farbenindustrie Akt Ges | Process for the preparation of complex metal compounds of o-oxyazo dyes |
DE617085C (en) * | 1932-06-05 | 1935-08-12 | I G Farbenindustrie Akt Ges | Process for the production of azo dyes |
-
1948
- 1948-02-26 CH CH273299D patent/CH273299A/en unknown
- 1948-02-26 CH CH273302D patent/CH273302A/en unknown
- 1948-02-26 CH CH273305D patent/CH273305A/en unknown
- 1948-02-26 CH CH273303D patent/CH273303A/en unknown
- 1948-02-26 CH CH273298D patent/CH273298A/en unknown
- 1948-02-26 CH CH273297D patent/CH273297A/en unknown
- 1948-02-26 CH CH273301D patent/CH273301A/en unknown
- 1948-02-26 CH CH270540D patent/CH270540A/en unknown
- 1948-02-26 CH CH273300D patent/CH273300A/en unknown
- 1948-12-24 CH CH274425D patent/CH274425A/en unknown
-
1949
- 1949-01-23 DE DE1949P0032243 patent/DE848979C/en not_active Expired
- 1949-01-27 DK DK28649A patent/DK74309C/en active
- 1949-01-31 AT AT166451D patent/AT166451B/en active
- 1949-02-23 NL NL145046A patent/NL69348C/xx active
Also Published As
Publication number | Publication date |
---|---|
CH274425A (en) | 1951-03-31 |
CH273305A (en) | 1951-01-31 |
CH273302A (en) | 1951-01-31 |
AT166451B (en) | 1950-08-10 |
CH270540A (en) | 1950-09-15 |
DK74309C (en) | 1952-06-16 |
CH273303A (en) | 1951-01-31 |
DE848979C (en) | 1952-09-11 |
CH273297A (en) | 1951-01-31 |
CH273301A (en) | 1951-01-31 |
CH273300A (en) | 1951-01-31 |
NL69348C (en) | 1951-08-15 |
CH273298A (en) | 1951-01-31 |
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