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DE472135C - Process for the preparation of acid dyes of the anthraquinone series - Google Patents

Process for the preparation of acid dyes of the anthraquinone series

Info

Publication number
DE472135C
DE472135C DEI27091D DEI0027091D DE472135C DE 472135 C DE472135 C DE 472135C DE I27091 D DEI27091 D DE I27091D DE I0027091 D DEI0027091 D DE I0027091D DE 472135 C DE472135 C DE 472135C
Authority
DE
Germany
Prior art keywords
preparation
acid dyes
anthraquinone series
aminoanthraquinone
thiohydrins
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
Application number
DEI27091D
Other languages
German (de)
Inventor
Dr Martin Corell
Dr Georg Kraenzlein
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DEI27091D priority Critical patent/DE472135C/en
Priority claimed from DEI27033D external-priority patent/DE455639C/en
Priority to FR626339D priority patent/FR626339A/en
Application granted granted Critical
Publication of DE472135C publication Critical patent/DE472135C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • 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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • 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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/56—Mercapto-anthraquinones
    • C09B1/58—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals
    • 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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/56—Mercapto-anthraquinones
    • C09B1/58—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals
    • C09B1/60—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals substituted by aliphatic, cycloaliphatic or araliphatic radicals
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Description

DEUTSCHES REICHGERMAN EMPIRE

AUSGEGEBEN AM
28. FEBRUAR 1929ISSUED ON
FEBRUARY 28, 1929

REICHSPATENTAMTREICH PATENT OFFICE

PATENTSCHRIFTPATENT LETTERING

...;.,......«■'"' KLASSE 22b GRUPPE...;., ... ... «■ '"' CLASS 22b GROUP

I. G. Farbenindustrie Akt-Ges. in Frankfurt a. M.*)I. G. Farbenindustrie Akt-Ges. in Frankfurt a. M. *)

Patentiert im Deutschen Reiche vom 18. Dezember 1925 abPatented in the German Empire on December 18, 1925

o-Aminoanthrachinonthiohydrine gehen bei der Behandlung mit sauren Kondensationsmitteln unter energischen Bedingungen in Thiomorpholine der Anthrachinonreihe über (vergleiche Patent 462 799).When treated with acidic condensing agents, o-Aminoanthraquinone thiohydrins turn into thiomorpholines under vigorous conditions the anthraquinone series (see patent 462,799).

Es wurde nun gefunden, daß bei der Behandlung von o-Aminoanthrachinonthiohydrinen mit konzentrierter Schwefelsäure oder Oleum nnter milden Bedingungen eine Sulfierung der o-Aminoanthrachinonthiohydrine eintritt und sehr wertvolle saure Farbstoffe entstehen. Dies war überraschend, da man nicht annehmen konnte, daß sich bei den Körpern des Typus:It has now been found that in the treatment of o-aminoanthraquinone thiohydrins with concentrated sulfuric acid or oleum under mild conditions a sulphonation of the o-Aminoanthraquinone thiohydrine occurs and very valuable acidic dyes are formed. this was surprising, since one could not assume that the bodies of the type:

CO NH9 CO NH 9

S -CH2-CH2OHS -CH 2 -CH 2 OH

die Kondensation zu den entsprechenden Thiomorpholinen überhaupt würde verhindern lassen.the condensation to the corresponding thiomorpholines would prevent at all permit.

BeispieleExamples

i. 5 Gewichtsteile i-Aminoanthrachinon-2-thiohydrin werden mit 50 Gewichtsteilen konzentrierter Schwefelsäure so lange auf 30 bis 35 ° erhitzt, bis vollkommene Wasserlöslichkeit erreicht ist. Durch Eingießen in Wasser wird die neue Sulfosäure ausgeschieden, abgesaugt und mit Kochsalzlösung neutral gewaschen und vorsichtig getrocknet. Der so erhaltene Farbstoff färbt in saurem Bade auf Wolle in sehr klaren, egalen roten Tönen an.i. 5 parts by weight of i-aminoanthraquinone-2-thiohydrin are with 50 parts by weight of concentrated sulfuric acid so long at 30 to 35 ° heated until complete solubility in water is achieved. By pouring it into water, the new sulfonic acid excreted, filtered off with suction and washed neutral with saline solution and carefully dried. The dye thus obtained dyes wool in an acidic bath in very clear, even red tones.

Wird das 1,4-Diamino-2-chlor-3-thiohydrinanthrachinon in ähnlicher Weise sulfiert, so entsteht ein sehr klares Violett. Aus dem o-Dithiohydrin des i, 5-Diaminoanthrachinons entsteht ein Rotbraun. Auf diese Weise ist es unter Verwendung der in dem Patent 455 639 beschriebenen o-Aminoanthrachinonthiohydrine möglich, eine große Mannigfaltigkeit neuer saurer Anthrachinonfarbstoffe zu erzeugen. Ähnlich wie konzentrierte Schwefelsäure wirkt Oleum oder Chlorsulfonsäure unter milden Bedingungen.Is the 1,4-diamino-2-chloro-3-thiohydrinanthraquinone sulfated in a similar way, the result is a very clear violet. From the o-dithiohydrin of the 1.5-diaminoanthraquinone results in a red-brown. That way it's under Use of the o-aminoanthraquinone thiohydrins described in patent 455,639 possible to produce a wide variety of new acidic anthraquinone dyes. Similar to concentrated sulfuric acid acts oleum or chlorosulfonic acid under mild conditions.

2. 5 Gewichtsteile i-Amino-4-p-toluidoanthfachinon-2-thiohydrin werden mit 50* Gewichtsteilen Schwefelsäure 66 ° Be so lange auf 35 bis 40 ° erwärmt, bis Wasserlöslichkeit eingetreten ist. Die wie in Beispiel 1 aufgearbeitete Sulfosäure färbt auf Wolle aus saurem Bade in klaren blauen Tönen.2. 5 parts by weight of i-amino-4-p-toluidoanthfachinone-2-thiohydrin are heated to 35 to 40 ° with 50 * parts by weight of 66 ° Be sulfuric acid until water solubility has occurred. The sulfonic acid worked up as in Example 1 dyes wool from an acid bath in clear blue tones.

Claims (1)

Patentanspruch:Claim: Verfahren zur Darstellung von Säurefarbstoffen der Anthrachinonreihe, dadurch gekennzeichnet, daß man die o-Aminoanthrachinonthiohydrine mit sulfierenden Mitteln unter Bedingungen behandelt, welche die Umwandlung in die entsprechenden Thiomorpholine verhindern.Process for the preparation of acid dyes of the anthraquinone series, thereby characterized in that the o-aminoanthraquinone thiohydrins are treated with sulphurizing agents under conditions which prevent the conversion into the corresponding thiomorpholines. *) Von dem Patentsucher sind als die Erfinder angegeben worden:*) The patent seeker indicated the following as the inventors:
DEI27091D 1925-12-17 1925-12-17 Process for the preparation of acid dyes of the anthraquinone series Expired DE472135C (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DEI27091D DE472135C (en) 1925-12-17 1925-12-17 Process for the preparation of acid dyes of the anthraquinone series
FR626339D FR626339A (en) 1925-12-17 1926-12-16 Process for the preparation of condensation products of the anthraquinone series containing nitrogen

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEI27091D DE472135C (en) 1925-12-17 1925-12-17 Process for the preparation of acid dyes of the anthraquinone series
DEI27033D DE455639C (en) 1925-12-17 1925-12-17 Process for the preparation of nitrogen-containing condensation products of the anthraquinone series

Publications (1)

Publication Number Publication Date
DE472135C true DE472135C (en) 1929-02-28

Family

ID=25981339

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI27091D Expired DE472135C (en) 1925-12-17 1925-12-17 Process for the preparation of acid dyes of the anthraquinone series

Country Status (2)

Country Link
DE (1) DE472135C (en)
FR (1) FR626339A (en)

Also Published As

Publication number Publication date
FR626339A (en) 1927-09-03

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