DE1133052B - Process for the preparation of water-insoluble disazo dyes - Google Patents

Process for the preparation of water-insoluble disazo dyes

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Publication number
DE1133052B
DE1133052B DEF29030A DEF0029030A DE1133052B DE 1133052 B DE1133052 B DE 1133052B DE F29030 A DEF29030 A DE F29030A DE F0029030 A DEF0029030 A DE F0029030A DE 1133052 B DE1133052 B DE 1133052B
Authority
DE
Germany
Prior art keywords
water
oxynaphthoylamino
oxynaphthalene
preparation
disazo dyes
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
DEF29030A
Other languages
German (de)
Inventor
Dr Herbert Nakaten
Dr Joachim Ribka
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.)
Hoechst AG
Original Assignee
Hoechst 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 Hoechst AG filed Critical Hoechst AG
Priority to DEF29030A priority Critical patent/DE1133052B/en
Priority to CH852660A priority patent/CH384112A/en
Priority to GB2618560A priority patent/GB955981A/en
Priority to BE593531A priority patent/BE593531A/en
Publication of DE1133052B publication Critical patent/DE1133052B/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
    • C08K5/23—Azo-compounds
    • C08K5/235—Diazo and polyazo compounds
    • 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
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02—Disazo dyes
    • C09B35/039—Disazo dyes characterised by the tetrazo component
    • C09B35/28—Disazo dyes characterised by the tetrazo component the tetrazo component containing two aryl nuclei linked by at least one of the groups —CON<, —SO2N<, —SO2—, or —SO2—O—

Description

Verfahren zur Herstellung von wasserunlöslichen Disazofarbstoffen Es wurde gefunden, daß man wertvolle, wasserunlösliche Disazofarbstoffe erhält, wenn man die Tetrazoniumverbindungen aus Aminen der allgemeinen Formel worin X Wasserstoff, ein Halogenatom, eine Alkyl-oder Alkoxygruppe und Y einen Rest der Benzol- oder Diphenylreihe bedeutet, mit 2-Oxynaphthalin-3-carbonsäure, 2-Oxynaphthalin-3-carbonsäureamid oder 2-Oxynaphthalin-3-carbonsäurearylamiden kuppelt.Process for the preparation of water-insoluble disazo dyes It has been found that valuable, water-insoluble disazo dyes are obtained if the tetrazonium compounds are obtained from amines of the general formula wherein X denotes hydrogen, a halogen atom, an alkyl or alkoxy group and Y denotes a radical of the benzene or diphenyl series, with 2-oxynaphthalene-3-carboxylic acid, 2-oxynaphthalene-3-carboxamide or 2-oxynaphthalene-3-carboxylic acid arylamides.

Die Herstellung der erfindungsgemäß verwendeten Diaminoverbindungen kann nach bekannten Verfahren erfolgen, beispielsweise durch Kondensation von 3-Nitrobenzoesäure, 3-Nitrobenzoesäurehalogeniden oder deren in 4-Stellung substituierten Derivate mit 1,4-Diaminobenzolen oder 4;4'-Diaminodiphenylen und anschließende Reduktion der so erhaltenen Nitroverbindungen. Für die Kondensation mit den Diaminen kommen außer der 3-Nitrobenzoesäure beispielsweise 3-Nitro-4-chlorbenzoesäure, 3-Nitro-4-methoxybenzoesäure oder 3-Nitro-4-rnethylbenzoesäure in Betracht. Als Diamine können z. B. 1,4-Diaminobenzol, 4,4'-Diaminodiphenyl, 4,4'-Diamino-3,3'-dimethoxydiphenyl, 4,4'-Diamino-3,3'-dimethyldiphenyl oder 4,4'-Diamino-3,3'-dichlordiphenyl Verwendung finden.The preparation of the diamino compounds used according to the invention can be carried out by known methods, for example by condensation of 3-nitrobenzoic acid, 3-nitrobenzoic acid halides or their derivatives substituted in the 4-position with 1,4-diaminobenzenes or 4; 4'-diaminodiphenylene and subsequent reduction of the nitro compounds thus obtained. Except for the condensation with the diamines of 3-nitrobenzoic acid, for example 3-nitro-4-chlorobenzoic acid, 3-nitro-4-methoxybenzoic acid or 3-nitro-4-methylbenzoic acid into consideration. As diamines, for. B. 1,4-diaminobenzene, 4,4'-diaminodiphenyl, 4,4'-diamino-3,3'-dimethoxydiphenyl, 4,4'-diamino-3,3'-dimethyldiphenyl or 4,4'-diamino-3,3'-dichlorodiphenyl use.

Als Azokomponenten kommen bei dem vorliegenden Verfahren 2-Oxynaphthalin-3-carbonsäure, 2-Oxynaphthalin-3-carbonsäureamid, 2-Oxynaphthalin-3-carbonsäurephenylamid und dessen im Phenylrest durch Halogenatome, Alkyl- oder Alkoxygruppen substituierten Derivate sowie 2-Oxynaphthalin-3-carbonsäurenaphthylamide, die frei von wasserlöslichmachenden Gruppen, wie Carbonsäure- oder Sulfonsäuregruppen, sind, in Betracht.The azo components used in the present process are 2-oxynaphthalene-3-carboxylic acid, 2-oxynaphthalene-3-carboxamide, 2-oxynaphthalene-3-carboxylic acid phenylamide and its derivatives substituted in the phenyl radical by halogen atoms, alkyl or alkoxy groups as well as 2-oxynaphthalene-3-carboxylic acid naphthylamides, which are free from water-solubilizing agents Groups such as carboxylic acid or sulfonic acid groups are possible.

Die Herstellung der Farbstoffe erfolgt nach an sich bekannten Verfahren, beispielsweise durch Kuppeln. der tetrazotierten Diamine mit den Azokomponenten in wäßriger Lösung in Gegenwart eines Dispergiermittels.The dyes are produced by processes known per se, for example by coupling. the tetrazotized diamines with the azo components in aqueous solution in the presence of a dispersant.

Die Farbstoffe stellen wasserunlösliche Pigmente dar, die sich durch eine sehr hohe Lösungsrnittelechtheit auszeichnen. Sie eignen sich insbesondere zum Färben von Lacken und von thermoplastischen Massen sowie für den Pigmentdruck.The dyes are water-insoluble pigments that stand out are characterized by a very high solvent fastness. They are particularly suitable for coloring lacquers and thermoplastic materials as well as for pigment printing.

Gegenüber dem aus der USA.-Patentschrift 2001526 bekannten wasserunlöslichen Disazofarbstoff aus tetrazotiertem N,N'-Bis-(5'-amino-2'-methoxyphenyl)-terephthalsäureamid und 2,3-Oxynaphthoylaminobenzol zeichnen sich die verfahrensgemäß erhältlichen wasserunlöslichen Disazofarbstoffe analoger Zusammensetzung durch eine bessere Ausblutechtheit der Polyvinylchloridfärbungen aus.Compared to the water-insoluble one known from US Pat. No. 2001526 Disazo dye from tetrazotized N, N'-bis (5'-amino-2'-methoxyphenyl) -terephthalic acid amide and 2,3-oxynaphthoylaminobenzene are the water-insoluble ones obtainable according to the process Disazo dyes of an analogous composition due to better resistance to bleeding Polyvinyl chloride dye.

Beispiel 1 41,5 Gewichtsteile 1,4-Di-(3'-amino-4'-chlorbenzoylamino)-benzol werden in. 500 Volumteilen Eisessig und 120 Volumteilen 5 n-Salzsäure verrührt und durch Zugabe von 40 Volumteilen 5 n-Natriumnitritlösung tetrazotiert. Die erhaltene Tetrazolösung wird mit Wasser auf 4000 Volumteile verdünnt, geklärt und mit einer wäßrigen Suspension von 60 Gewichtsteilen 1-(2',3'-Oxynaphthoylamino)-2-methoxybenzol, die durch Lösen dieser Verbindung in verdünnter Natronlauge und Ausfällen mit Eisessig in Gegenwart eines Einwirkungsproduktes von etwa 20 Mol Äthylenoxyd auf 1 Mol Octodecylalkohol hergestellt wurde, vereinigt.Example 1 41.5 parts by weight of 1,4-di- (3'-amino-4'-chlorobenzoylamino) benzene are stirred in. 500 parts by volume of glacial acetic acid and 120 parts by volume of 5N hydrochloric acid and Tetrazotized by adding 40 parts by volume of 5N sodium nitrite solution. The received Tetrazo solution is diluted with water to 4000 parts by volume, clarified and with a aqueous suspension of 60 parts by weight of 1- (2 ', 3'-oxynaphthoylamino) -2-methoxybenzene, by dissolving this compound in dilute sodium hydroxide solution and precipitating it with glacial acetic acid in the presence of an action product of about 20 moles of ethylene oxide to 1 mole of octodecyl alcohol was made, united.

Der nach Beendigung der Kupplung abgeschiedene Farbstoff wird abgesaugt, gewaschen und getrocknet. Er stellt ein orangefarbenes Pulver dar.The dye deposited after the coupling has ended is suctioned off, washed and dried. It is an orange powder.

Mit dem Farbstoff hergestellte Nitrocelluloselacke ergeben eine rote Lackierung von sehr guter Überspritzechtheit. Beim Einarbeiten in Polyvinylchlorid erhält man eine rote Färbung von sehr guter Ausblutechtheit. Beispiel 2 8,65 Gewichtsteile 1,4-Di-(3'-aminobenzoylamino)-benzol werden einige Stunden in 30 Volumteilen 5 n_ Salzsäure und 30 Volumteilen Wasser verrührt, mit Wasser verdünnt und bei Zimmertemperatur mit 10 Volumteilen 5 n-Natriumnitritlösung tetrazotiert.Nitrocellulose lacquers made with the dye give a red color Very good fastness to overmolding. When working in polyvinyl chloride a red coloration of very good fastness to bleeding is obtained. Example 2 8.65 parts by weight 1,4-Di- (3'-aminobenzoylamino) -benzene for a few hours in 30 parts by volume 5 n_ hydrochloric acid and 30 parts by volume of water, diluted with water and kept at room temperature Tetrazotized with 10 parts by volume of 5N sodium nitrite solution.

Die geklärte Tetrazolösung wird, wie in Beispiel 1 beschrieben, mit einer wäßrigen Suspension von 15 Gewichtsteilen 1-(2',3'-Oxynäphthoylamino)-2-methoxybenzol vereinigt. Der nach Beendigung der Kupplung abgeschiedene Farbstoff wird abgesaugt, gewaschen und getrocknet. Er stellt ein gelbstichigrotes Pulver dar.The clarified tetrazo solution is, as described in Example 1, with an aqueous suspension of 15 parts by weight of 1- (2 ', 3'-Oxynäphthoylamino) -2-methoxybenzene united. The dye deposited after the coupling has ended is suctioned off, washed and dried. It is a yellow-tinged red powder.

Die nachstehende Tabelle enthält noch eine Anzahl von weiteren, erfindungsgemäß erhältlichen Farbstoffen sowie deren Farbtöne: Diazokomponente Azokomponente Farbton 1,4-Di-(3'-aminobenzoylamino)-benzol 1 - (2',3' - Oxynaphthoylamino) - 2,4 - dimethoxy - Rot 5-chlorbenzol 1,4-Di-(3'-amino-4'-chlorbenzoylamino)-benzol desgl. Karte desgl. 1- (2',3'- Oxynaphthoylamino) - 4 - methoxybenzol Rot desgl. 2-Oxynaphthahn-3-carbonsäure Rot desgl. 2-Oxynaphthalin-3-carbonsäureamid Orange 1,4-Di-(3'-amino-4'-methoxybenzoylamino)-benzol 1 - (2',3'-Oxynaphthoylamino) - 2,5 - dimethoxy - Karmin 4-chlorbengol desgl. 1 - (2',3' - Oxynaphthoylamino) - 2,4 - dimethoxy - Bordo 5-chlorbenzol desgl. 1-(2',3'-Oxynaphtoylamino)-4-methoxybenzol Karmin 1;4-Di-(3'-amino-4'-methylbenzoylamino)-benzol 1 - (2',3' - Oxynaphthoylamino) - 2,5 - dimethoxy - Karmin 4-chlorbenzol desgl. 1 - (2',3' - Oxynaphthoylamino) - 2,4 - dimethoxy - Karmin 5-chlorbenzol desgl. 1- (2',3'- Oxynaphthoylamino) - 2 - methoxybenzol Rot 4,4'-Di-(3"-amino-4"-chlorbenzoylamino)-3,3'-di- 1- (2',3' - Oxynaphthoylamino) - 2 - methoxybenzol Rot methoxydiphenyl 4,4'- Di - (3" - amino - 4" - methoxybenzoylamino) - 1 - (2',3' - Oxynaphthoylamino) - 2,5 - dimethoxy - Karmin 3,3'-dimethyldiphenyl 4-chlorbenzol desgl. 1 - (2',3' - Oxynaphthoylamino) - 2,4 - dimethoxy - Karmin. 5-chlorbenzol desgl. 1-(2',3'-Oxynaphthoylamino)-2-methylbenzol Karmin desgl. 1- (2',3' - Oxynaphthoylamino)-2-methyl-5-chlor- Karmin benzol 4,4'- Di- (3" - amino - 4" - methylbenzoylamino) - di - 1-(2',3'-Oxynaphthoylamino)-2-methoxybenzol Rot phenyl 1;4-Di-(3'-amino-4'-chlorbenzoylamino)-benzol 1-(2',3'-Oxynaphthoylamino)-2-äthoxybenzol Orange desgl. 1 - (2',3' - Oxynaphthoylamino) - 2,4 - dimethoxy - Rot 5-chlorbenzol 4,4'- Di - (3" - amino - 4" - methoxybenzoylamino) - 1-(2',3'-Oxynaphthoylamino)-4-methoxybenzol Karmin 3,3'-dichlordiphenyl The table below also contains a number of other dyes obtainable according to the invention and their color shades: Diazo component Azo component hue 1,4-di- (3'-aminobenzoylamino) -benzene 1 - (2 ', 3' - oxynaphthoylamino) - 2,4 - dimethoxy - red 5-chlorobenzene 1,4-Di- (3'-amino-4'-chlorobenzoylamino) -benzene like card likewise 1- (2 ', 3'-oxynaphthoylamino) - 4 - methoxybenzene red Likewise. 2-Oxynaphthahn-3-carboxylic acid red likewise. 2-oxynaphthalene-3-carboxamide orange 1,4-Di- (3'-amino-4'-methoxybenzoylamino) -benzene 1- (2 ', 3'-oxynaphthoylamino) -2,5-dimethoxy-carmine 4-chlorobenzene likewise. 1 - (2 ', 3' - oxynaphthoylamino) - 2,4 - dimethoxy - Bordo 5-chlorobenzene likewise 1- (2 ', 3'-oxynaphtoylamino) -4-methoxybenzene carmine 1; 4-di- (3'-amino-4'-methylbenzoylamino) -benzene 1 - (2 ', 3' - oxynaphthoylamino) - 2,5 - dimethoxy - carmine 4-chlorobenzene likewise 1 - (2 ', 3' - oxynaphthoylamino) - 2,4 - dimethoxy - carmine 5-chlorobenzene likewise 1- (2 ', 3'-oxynaphthoylamino) - 2 - methoxybenzene red 4,4'-di- (3 "-amino-4" -chlorobenzoylamino) -3,3'-di- 1- (2 ', 3' - oxynaphthoylamino) -2 - methoxybenzene red methoxydiphenyl 4,4'-di - (3 "- amino - 4" - methoxybenzoylamino) - 1 - (2 ', 3' - oxynaphthoylamino) - 2,5 - dimethoxy - carmine 3,3'-dimethyldiphenyl 4-chlorobenzene likewise 1 - (2 ', 3' - oxynaphthoylamino) - 2,4 - dimethoxy - carmine. 5-chlorobenzene likewise 1- (2 ', 3'-oxynaphthoylamino) -2-methylbenzene carmine likewise 1- (2 ', 3' - oxynaphthoylamino) -2-methyl-5-chloro-carmine benzene 4,4'-di- (3 "- amino - 4" - methylbenzoylamino) - di - 1- (2 ', 3'-oxynaphthoylamino) -2-methoxybenzene red phenyl 1; 4-Di- (3'-amino-4'-chlorobenzoylamino) -benzene 1- (2 ', 3'-oxynaphthoylamino) -2-ethoxybenzene Orange likewise. 1 - (2 ', 3' - oxynaphthoylamino) - 2,4 - dimethoxy - red 5-chlorobenzene 4,4'-di - (3 "- amino - 4" - methoxybenzoylamino) - 1- (2 ', 3'-oxynaphthoylamino) -4-methoxybenzene carmine 3,3'-dichlorodiphenyl

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von wasserunlöslichen Disazofarbstoffen, dadurch gekennzeichnet, daß man die Tetrazoniumverbindungen aus Aminen der allmemeinen Formel worin X Wasserstoff, ein Halogenatom, eine Alkyl-oder Alkoxygruppe und Y einen Rest der Benzol-oder Diphenylreihe bedeuten, mit 2-Oxynaphthalin-3-carbonsäure, 2-Oxynaphthalin-3-carbonsäureamid oder - 2-Oxynaphthalin-3-Carbonsäurearylamiden kuppelt. In Betracht gezogene Druckschriften: USA: Patentschrift Nr. 2 001526. PATENT CLAIM: Process for the preparation of water-insoluble disazo dyes, characterized in that the tetrazonium compounds are obtained from amines of the general formula where X is hydrogen, a halogen atom, an alkyl or alkoxy group and Y is a radical of the benzene or diphenyl series, with 2-oxynaphthalene-3-carboxylic acid, 2-oxynaphthalene-3-carboxamide or - 2-oxynaphthalene-3-carboxylic acid arylamides. References considered: USA: Patent No. 2,001526.
DEF29030A 1959-07-28 1959-07-28 Process for the preparation of water-insoluble disazo dyes Pending DE1133052B (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
DEF29030A DE1133052B (en) 1959-07-28 1959-07-28 Process for the preparation of water-insoluble disazo dyes
CH852660A CH384112A (en) 1959-07-28 1960-07-26 Process for the preparation of water-insoluble disazo dyes
GB2618560A GB955981A (en) 1959-07-28 1960-07-27 Water-insoluble disazo-dyestuffs and process for their manufacture
BE593531A BE593531A (en) 1959-07-28 1960-07-28 Disazo dyes and their preparation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF29030A DE1133052B (en) 1959-07-28 1959-07-28 Process for the preparation of water-insoluble disazo dyes

Publications (1)

Publication Number Publication Date
DE1133052B true DE1133052B (en) 1962-07-12

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Application Number Title Priority Date Filing Date
DEF29030A Pending DE1133052B (en) 1959-07-28 1959-07-28 Process for the preparation of water-insoluble disazo dyes

Country Status (4)

Country Link
BE (1) BE593531A (en)
CH (1) CH384112A (en)
DE (1) DE1133052B (en)
GB (1) GB955981A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2236250A1 (en) * 1971-07-26 1973-02-08 Acna NEW DIAZO PIGMENTS, THEIR PRODUCTION AND USE

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2001526A (en) * 1933-03-30 1935-05-14 Du Pont Azo dyes and method for their preparation

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2001526A (en) * 1933-03-30 1935-05-14 Du Pont Azo dyes and method for their preparation

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2236250A1 (en) * 1971-07-26 1973-02-08 Acna NEW DIAZO PIGMENTS, THEIR PRODUCTION AND USE

Also Published As

Publication number Publication date
GB955981A (en) 1964-04-22
BE593531A (en) 1961-01-30
CH384112A (en) 1964-11-15

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