CH273297A - 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
- CH273297A CH273297A CH273297DA CH273297A CH 273297 A CH273297 A CH 273297A CH 273297D A CH273297D A CH 273297DA CH 273297 A CH273297 A CH 273297A
- 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. <B>Es</B> wurde gefunden, dass man zu einem wertvollen metallhaltigen Monoazofarbstoff nelangt, wenn man auf einen Monoazofarb- stoff der Formel
EMI0001.0006
-unter Bedingungen, bei denen eine Abspal tung der Alkylgruppe des in o-Stellung zur Azogruppe befindlichen -0-Alkyl-Restes stattfindet., chromabgebende Mittel einwirken lässt.
Der neue metallhaltige Farbstoff ist eine dunkelgefärbte Substanz, welche sich in Was ser mit blauer, in verdünnten Alka.Iihydroxyd- lösungen mit rubinroter und in konz. Schwe felsäure mit schmutzig violetter Farbe löst und. Wolle aus schwefelsaurem Bade in gleichmässigen, echten rotstichig blauen Tö nen färbt, welche bei Kunstlicht praktisch denselben Farbton wie bei Tageslicht zeigen.
Die beim vorliegenden Verfahren als Aus gangsstoffe dienenden, der obigen Formel entsprechenden Monoazofarbstoffe können hergestellt werden, indem man ein .diazo- tiertes 2-Allioxy-4-chlor-5-methoxy .1.-amino- benzol mit 1-Oxynaphthalin-3,6-disiüfonsäure kuppelt.
Die in 2-Stellung der Diazokompo- nente befindliche Alkoxygruppe enthält vor zugsweise mir wenige, beispielsweise 1 bis 4 Kohlenstoffatome. Als besonders zweckmä ssiger Ausgangsstoff für das vorliegende Ver fahren erweist sich der aus diazotiertein 2,
5-Dimethoxy-l-amino-4-chlorbenzol erhält liehe Monoazofarbstoff. Die Diazotierung des 2-Alkoxy-4-chlor- 5-methoxy 1-aminobenzols kann in üblicher, an sich bekannter Weise, z. B. mit Hilfe von Natritunnitrit und Salzsäure erfolgen.. Die Kupplung der Dia.zoverbindung mit der 1-Oxynaphthalin-3,6-disulfonsäure erfolgt zweckmässig in alkalischem, beispielsweise natriumcarbonatalkalischem Medium.
Gegebe nenfalls kann .die Kupplung auch in Anwe senheit geeigneter Lösungsmittel, wie Alkohol oder Pyridin durchgeführt werden.
Die beim vorliegenden Verfahren als Aus- gangsstoffe dienenden Monoazofarbstoffe kön nen gewünachtenfalls 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 wer den.
In .der Regel ist es hierbei notwendig, das Kupplungsgemisch vor der Durchführung der Reaktion mit dem chromabgebenden Mittel auf den für die Reaktion günstigen p$.Wert, d. h. auf schwach mineralsaure Reaktion ein zustellen. Als chromabgebende Mittel kommen vor allem die Salze ,des dreiwertigen Chroms, wie Chromfluorid, Chromsulfate, Chromacetat und Chromformiat in Betracht.
Die Behandlung mit den chromabgebenden Mitteln erfolgt unter solchen Bedingungen, bei welchen eine Abspaltung .der Alkylgruppe des in o-Stel- lung zur Azogruppe befindlichen -0-Alkyl- Restes stattfindet. Diese Abspaltung unter gleichzeitiger Bildung der komplexen Chrom verbindung lässt sich nach an sich bekannter Methode durchführen, indem man die Be handlung mit dem chromabgebenden Mittel, z.
B. mit Chrornformiat oder Chromsulfat in wässrigem, vorzugsweise mineralsaurem Me dium unter Druck bei erhöhter Temperatur, , z. B. Temperatur zwischen 110 und 1400 vor- nimmt <I>Beispiel:
</I> 18,8 Teile 2,5-Dimethoxy-1-amino-4-chlor- benzol werden in üblicher Weise in Gegen wert von 30 Teilen 30 o/oiger Salzsäure mit 7 Teilen Natriumnitrit diazotiert. Die erhal tene, klare Lösung der Diazoverbindimg wird unter gutem Rühren zu einer auf 100 gekühl ten Lösung von 31 Teilen 1-Oxynaphthalin@- 3,
6-disulfonsäure und 30 Teilen wasserfreiem Natriumcarbonat in 400 Teilen Wasser zuflie ssen gelassen. Der entstandene Farbstoff fällt zum grössten Teil aus. Er stellt getrocknet eine dunkel gefärbte Substanz dar, .die sich in Wasser und verdünnter Natriumcarbonat- lösung mit rubinroter und in konz. Schwefel säure mit blauer .
Farbe löst und Wolle aus saurem Bade in blaustichig roten Tönen färbt.
Dieser Farbstoff kann ohne Zwischenab- scheidung in die komplexe Chromverbindung übergeführt werden. Zu diesem Zweck wird das nach obigen Angaben erhaltene Kupp- lungsgemisch mit 200 Teilen Wasser ver dünnt und 10 o/oige Schwefelsäure bis zur schwach mineralsauren Reaktion zugegeben. Nach Zugabe einer 5,7 Teile Cr enthaltenden Menge Chromsulfat [Cry(S0,)
3] erhitzt man das Reaktionsgemisch im verbleiten Rühr- autoklaven auf 120 bis 1250 und rührt wäh rend 15 Stunden bei dieser Temperatur. Die entstandene Chromverbindung fällt zum grossen Teil aus und wird nach dem Erkalten auf Ratuntemperatur abfiltriert und ge trocknet.
Process for the preparation of a metal-containing monoazo dye. <B> It </B> has been found that a valuable metal-containing monoazo dye is obtained if one uses a monoazo dye of the formula
EMI0001.0006
Under conditions in which the alkyl group of the -0-alkyl radical in the o-position to the azo group is split off., lets chromium-donating agents act.
The new metal-containing dye is a dark-colored substance, which in water with blue, in dilute alkali hydroxide solutions with ruby red and in conc. Sulfur acid dissolves with dirty purple color and. Wool from sulfuric acid bath dyes in even, real, reddish-tinged blue tones, which show practically the same hue in artificial light as in daylight.
The monoazo dyes which are used as starting materials in the present process and correspond to the above formula can be prepared by adding a .diazo-tated 2-allioxy-4-chloro-5-methoxy .1.-aminobenzene with 1-oxynaphthalene-3, 6-disifonic acid couples.
The alkoxy group in the 2-position of the diazo component preferably contains a few, for example 1 to 4, carbon atoms. A particularly useful starting material for the present process has proven to be the diazotized one 2,
5-Dimethoxy-1-amino-4-chlorobenzene is obtained from the monoazo dye. The diazotization of the 2-alkoxy-4-chloro-5-methoxy 1-aminobenzene can be carried out in a conventional manner known per se, e.g. B. with the help of sodium nitrite and hydrochloric acid .. The coupling of the dia.zo compound with the 1-oxynaphthalene-3,6-disulfonic acid is expediently carried out in an alkaline, for example sodium carbonate-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, the coupling compound can be used as a whole and without intermediate deposition for the treatment with the chromium donating agents.
As a rule, it is necessary here to bring the coupling mixture to the p value that is favorable for the reaction, i.e., the value, before the reaction with the chromium donating agent is carried out. H. adjust to weak mineral acid reaction. The salts of trivalent chromium, such as chromium fluoride, chromium sulfates, chromium acetate and chromium formate, are particularly suitable as chromium-releasing agents.
The treatment with the chromium-releasing agents is carried out under conditions under which the alkyl group of the -0-alkyl radical in the o-position to the azo group is split off. This elimination with the simultaneous formation of the complex chromium compound can be carried out according to a method known per se by treating the chromium-releasing agent, eg.
B. with chromium formate or chromium sulfate in aqueous, preferably mineral acid Me medium under pressure at elevated temperature, z. B. takes temperature between 110 and 1400 <I> Example:
18.8 parts of 2,5-dimethoxy-1-amino-4-chlorobenzene are diazotized with 7 parts of sodium nitrite in the customary manner in the equivalent of 30 parts of 30% hydrochloric acid. The clear solution of the diazo compound obtained is, with thorough stirring, to give a solution of 31 parts of 1-oxynaphthalene @ -3, cooled to 100,
6-disulfonic acid and 30 parts of anhydrous sodium carbonate in 400 parts of water are allowed to flow in. Most of the resulting dye precipitates. When dried, it is a dark colored substance, which dissolves in water and dilute sodium carbonate solution with ruby red and in conc. Sulfuric acid with blue.
Dye dissolves and dyes wool from acid baths in bluish red tones.
This dye can be converted into the complex chromium compound without intermediate separation. For this purpose, the coupling mixture obtained according to the above is diluted with 200 parts of water and 10% sulfuric acid is added until the reaction has a weak mineral acidity. After adding an amount of chromium sulfate containing 5.7 parts of Cr [Cry (S0,)
3] the reaction mixture is heated to 120 to 1250 in the leaded stirred autoclave and stirred for 15 hours at this temperature. The chromium compound formed largely precipitates out and, after cooling to the Ratun temperature, is filtered off and dried.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH273298T | 1948-02-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH273297A true CH273297A (en) | 1951-01-31 |
Family
ID=25731441
Family Applications (10)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH273298D CH273298A (en) | 1948-02-26 | 1948-02-26 | Process for the preparation of a metal-containing monoazo dye. |
CH273299D CH273299A (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. |
CH273302D CH273302A (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. |
CH273301D CH273301A (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. |
CH270540D CH270540A (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. |
CH274425D CH274425A (en) | 1948-02-26 | 1948-12-24 | Process for the preparation of a metal-containing monoazo dye. |
Family Applications Before (6)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH273298D CH273298A (en) | 1948-02-26 | 1948-02-26 | Process for the preparation of a metal-containing monoazo dye. |
CH273299D CH273299A (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. |
CH273302D CH273302A (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. |
CH273301D CH273301A (en) | 1948-02-26 | 1948-02-26 | Process for the preparation of a metal-containing monoazo dye. |
Family Applications After (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH270540D CH270540A (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. |
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) | CH273298A (en) |
DE (1) | DE848979C (en) |
DK (1) | DK74309C (en) |
NL (1) | NL69348C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
Families Citing this family (3)
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 |
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 CH273298D patent/CH273298A/en unknown
- 1948-02-26 CH CH273299D patent/CH273299A/en unknown
- 1948-02-26 CH CH273300D patent/CH273300A/en unknown
- 1948-02-26 CH CH273302D patent/CH273302A/en unknown
- 1948-02-26 CH CH273303D patent/CH273303A/en unknown
- 1948-02-26 CH CH273301D patent/CH273301A/en unknown
- 1948-02-26 CH CH273297D patent/CH273297A/en unknown
- 1948-02-26 CH CH270540D patent/CH270540A/en unknown
- 1948-02-26 CH CH273305D patent/CH273305A/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
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
Also Published As
Publication number | Publication date |
---|---|
CH270540A (en) | 1950-09-15 |
CH273302A (en) | 1951-01-31 |
CH273299A (en) | 1951-01-31 |
CH273305A (en) | 1951-01-31 |
CH273298A (en) | 1951-01-31 |
DE848979C (en) | 1952-09-11 |
AT166451B (en) | 1950-08-10 |
CH273300A (en) | 1951-01-31 |
DK74309C (en) | 1952-06-16 |
CH273303A (en) | 1951-01-31 |
CH273301A (en) | 1951-01-31 |
NL69348C (en) | 1951-08-15 |
CH274425A (en) | 1951-03-31 |
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