DE1163471B - Process for the preparation of a dye - Google Patents

Process for the preparation of a dye

Info

Publication number
DE1163471B
DE1163471B DEC21949A DEC0021949A DE1163471B DE 1163471 B DE1163471 B DE 1163471B DE C21949 A DEC21949 A DE C21949A DE C0021949 A DEC0021949 A DE C0021949A DE 1163471 B DE1163471 B DE 1163471B
Authority
DE
Germany
Prior art keywords
dye
preparation
acid
oxyanthraquinone
german patent
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.)
Pending
Application number
DEC21949A
Other languages
German (de)
Inventor
Dr Werner Zerweck
Dr Ernst Heinrich
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.)
Cassella Farbwerke Mainkur AG
Original Assignee
Cassella Farbwerke Mainkur 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 Cassella Farbwerke Mainkur AG filed Critical Cassella Farbwerke Mainkur AG
Priority to DEC21949A priority Critical patent/DE1163471B/en
Priority to FR868397A priority patent/FR1295299A/en
Priority to GB2641661A priority patent/GB913914A/en
Publication of DE1163471B publication Critical patent/DE1163471B/en
Pending legal-status Critical Current

Links

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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
    • C09B1/51—N-substituted amino-hydroxy anthraquinone
    • C09B1/516—N-acylated derivatives
    • 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
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/36—Dyes with acylated amino groups
    • C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid

Landscapes

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

Description

BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY

DEUTSCHESGERMAN

PATENTAMTPATENT OFFICE

AUSLEGESCHRIFTEDITORIAL

Internat. Kl.: C 09 bBoarding school Class: C 09 b

Deutsche Kl.: 22 b-3/03German class: 22 b-3/03

Nummer: 1163 471Number: 1163 471

Aktenzeichen: C 21949IV c / 22 bFile number: C 21949IV c / 22 b

Anmeldetag: 20. Juli 1960Filing date: July 20, 1960

Auslegetag: 20. Februar 1964Opened on: February 20, 1964

Es wurde gefunden, daß man einen wertvollen, Polyesterfasern echt färbenden Farbstoff erhält, wenn man 1,5-Diamino-4-oxyanthrachinon mit m-Methylbenzoesäure oder den funktioneilen Derivaten dieser Säure umsetzt, oder wenn man l,5-Di-(m-methylbenzoylamino)-anthrachinon nach den Verfahren der deutschen Patentschriften 213 500 und 238 488 mit konzentrierter bzw. rauchender Schwefelsäure bzw. mit anderen Oxydationsmitteln behandelt.It has been found that a valuable, polyester fiber fast coloring dye is obtained, if you 1,5-diamino-4-oxyanthraquinone with m-methylbenzoic acid or the functional derivatives this acid converts, or if one, 5-di (m-methylbenzoylamino) anthraquinone by the process of German patents 213 500 and 238 488 with concentrated or fuming sulfuric acid or treated with other oxidizing agents.

Der neue Farbstoff entspricht der FormelThe new dye conforms to the formula

CH3 CH 3

O NH-COO NH-CO

OC-NHO OHOC-NHO OH

Der erfindungsgemäß herstellbare Farbstoff besitzt beim Drucken auf Polyestergewebe eine größere Farbstärke als das aus der deutschen Patentschrift 238 488, Beispiel 1, bekannte 1,5-Dibenzoyl-amino-4-oxyanthrachinon bzw. das aus der deutschen Patentschrift 436 536 bekannte 1,5-Di-m-methoxybenzoyl-amino-4-oxyanthrachinon. The dye which can be prepared according to the invention has a larger one when printed on polyester fabric Color strength than the 1,5-dibenzoyl-amino-4-oxyanthraquinone known from German Patent 238 488, Example 1 or the 1,5-di-m-methoxybenzoyl-amino-4-oxyanthraquinone known from German patent specification 436 536.

.Beispiel.Example

Ein Gemisch aus 300 Teilen Monochlorbenzol, 12,7 Teilen l,5-Diamino-4-oxyanthrachinon und 23,1 Teilen m-Methylbenzoylchlorid wird ^Stunden auf 1200C erhitzt. Nach dem Erkalten wird der entstandene Farbstoff abgesaugt und zunächst mit Monochlorbenzol, dann mit Methanol ausgewaschen und getrocknet. Der Farbstoff, der bei 242 bis 244° C schmilzt, löst sich in konzentrierter Schwefelsäure mit blaustichigroter Farbe. Auf Polyesterfasern liefert er farbstarke, klare, blaustichigrote Färbungen und Drucke von hervorragenden Echtheitseigenschaften. A mixture of 300 parts of monochlorobenzene, 12.7 parts of l, 5-diamino-4-oxyanthrachinon and 23.1 parts of m-methylbenzoyl chloride is heated to 120 0 C ^ hours. After cooling, the resulting dye is filtered off with suction and washed first with monochlorobenzene and then with methanol and dried. The dye, which melts at 242 to 244 ° C, dissolves in concentrated sulfuric acid with a bluish-tinged red color. On polyester fibers, it provides strong, clear, bluish-tinged red dyeings and prints with excellent fastness properties.

Der gleiche Farbstoff wird erhalten durch Behandlung von l,5-Di-(m-methylbenzoylamino)-an-Verfahren zur Herstellung eines FarbstoffesThe same dye is obtained by treating 1,5-di- (m-methylbenzoylamino) -ane method for the production of a dye

Anmelder:Applicant:

Cassella Farbwerke Mainkur Aktiengesellschaft, Frankfurt/M.-FechenheimCassella Farbwerke Mainkur Aktiengesellschaft, Frankfurt / M.-Fechenheim

Als Erfinder benannt:Named as inventor:

Dr. Werner Zerweck, Frankfurt/M.,Dr. Werner Zerweck, Frankfurt / M.,

Dr. Ernst Heinrich, Frankfurt/M.-Fechenheim - -Dr. Ernst Heinrich, Frankfurt / M.-Fechenheim - -

thrachinon mit einem Oxydationsmittel gemäß den Verfahren der deutschen Patentschriften 213 500 und 238 488.thrachinone with an oxidizing agent according to the method of German patents 213 500 and 238 488.

Claims (1)

Patentanspruch:Claim: Verfahren zur Herstellung eines Farbstoffes der FormelProcess for the preparation of a dye of the formula NH-CONH-CO OC-NH O OHOC-NH O OH H3CH 3 C dadurch gekennzeichnet, daß man l,5-Diamino-4-oxyanthrachinon mit m-Methylbenzoesäure oder den funktioneilen Derivaten dieser Säure umsetzt oder daß man 1,5-Di-(m-methylbenzoylamino)-anthrachinon mit konzentrierter bzw. rauchender Schwefelsäure bzw. mit anderen Oxydationsmitteln behandelt.characterized in that l, 5-diamino-4-oxyanthraquinone with m-methylbenzoic acid or the functional derivatives of this acid are reacted or that 1,5-di- (m-methylbenzoylamino) anthraquinone is used treated with concentrated or fuming sulfuric acid or with other oxidizing agents. In Betracht gezogene Druckschriften:
Deutsche Patentschriften Nr. 238 488, 436 536.Considered publications:
German patent specifications No. 238 488, 436 536. Bei der Bekanntmachung der Anmeldung ist eine Färbetafel mit Erläuterungen ausgelegt worden.When the application was announced, a coloring table with explanations was laid out.
DEC21949A 1960-07-20 1960-07-20 Process for the preparation of a dye Pending DE1163471B (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
DEC21949A DE1163471B (en) 1960-07-20 1960-07-20 Process for the preparation of a dye
FR868397A FR1295299A (en) 1960-07-20 1961-07-19 New anthraquinone dye and its preparation
GB2641661A GB913914A (en) 1960-07-20 1961-07-20 An anthraquinone dyestuff and process for its manufacture

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEC21949A DE1163471B (en) 1960-07-20 1960-07-20 Process for the preparation of a dye

Publications (1)

Publication Number Publication Date
DE1163471B true DE1163471B (en) 1964-02-20

Family

ID=7017108

Family Applications (1)

Application Number Title Priority Date Filing Date
DEC21949A Pending DE1163471B (en) 1960-07-20 1960-07-20 Process for the preparation of a dye

Country Status (3)

Country Link
DE (1) DE1163471B (en)
FR (1) FR1295299A (en)
GB (1) GB913914A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU1594189A1 (en) * 1986-10-24 1990-09-23 Предприятие П/Я А-7850 Derivatives of 1-aminoantraquinone as dye with negative dichroism, and liquid-crystal material for optronic devices
CN110759822A (en) * 2018-07-27 2020-02-07 江苏恒正合生命科学有限公司 Preparation method of thymoquinone

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE238488C (en) *
DE436536C (en) * 1925-02-16 1926-11-03 I G Farbenindustrie Akt Ges Process for the preparation of Kuepen dyes of the anthraquinone series

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE238488C (en) *
DE436536C (en) * 1925-02-16 1926-11-03 I G Farbenindustrie Akt Ges Process for the preparation of Kuepen dyes of the anthraquinone series

Also Published As

Publication number Publication date
GB913914A (en) 1962-12-28
FR1295299A (en) 1962-06-01

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