DE1021105B - Process for the preparation of a water-insoluble monoazo dye - Google Patents

Process for the preparation of a water-insoluble monoazo dye

Info

Publication number
DE1021105B
DE1021105B DEF20827A DEF0020827A DE1021105B DE 1021105 B DE1021105 B DE 1021105B DE F20827 A DEF20827 A DE F20827A DE F0020827 A DEF0020827 A DE F0020827A DE 1021105 B DE1021105 B DE 1021105B
Authority
DE
Germany
Prior art keywords
water
dye
preparation
monoazo dye
insoluble monoazo
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
DEF20827A
Other languages
German (de)
Inventor
Dr Ernst Fischer
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 DEF20827A priority Critical patent/DE1021105B/en
Publication of DE1021105B publication Critical patent/DE1021105B/en
Pending legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F1/00—General methods for the manufacture of artificial filaments or the like
    • D01F1/02—Addition of substances to the spinning solution or to the melt
    • D01F1/06—Dyes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
    • C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
    • C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D17/00—Pigment pastes, e.g. for mixing in paints
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Textile Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Coloring (AREA)

Description

Verfahren zur Herstellung eines wasserunlöslichen Monoazofarbstoffes Es wurde gefunden, daß man zu einem wertvollen wasserunlöslichen Monoazofarbstoff gelangt, wenn man die Diazoniumverbindung aus 1 Amino-2-methoxy-benzol-5-carbonsäure-phenylamid mit 1-(2',3'-Oxvnaphthoylamino)-2,5-dimethoxy-4-chlorbenzol kuppelt.Process for the preparation of a water-insoluble monoazo dye It has been found that this leads to a valuable water-insoluble monoazo dye when the diazonium compound is obtained from 1-amino-2-methoxy-benzene-5-carboxylic acid phenylamide couples with 1- (2 ', 3'-oxynaphthoylamino) -2,5-dimethoxy-4-chlorobenzene.

Der Farbstoff läßt sich sowohl in Substanz als auch auf der Faser herstellen und ergibt dabei lebhafte blaustichige Rottöne. Den in Substanz hergestellten Farbstoff kann man durch Klotzen oder im Pigmentdruckverfahren auf Textilien aufbringen und auch - bei Zusatz zu den Spinnlösungen - zur Erzeugung spinngefärbter Acetat- und Viskosekunstseide verwenden.The dye can be used both in substance and on the fiber and produces lively blue-tinged red tones. The one produced in substance Dye can be applied to textiles by padding or by pigment printing and also - when added to the spinning solutions - to produce spun-dyed acetate and use viscose rayon.

Der neue Farbstoff eignet sich gleichfalls für die Zubereitung von Farblacken und kann weiterhin zur Herstellung gefärbter Filme in Massen aus Celluloseestern oder -äthern eingebracht oder auch zum Färben von Natur-und Kunstharzen, wie den Kondensationsprodukten aus Formaldehyd und Harnstoff, Phenolen oder Aminen, sowie von Kautschuk und Polyvinylverbindungen verwendet werden.The new dye is also suitable for the preparation of Color lakes and can continue to produce colored films in bulk from cellulose esters or ethers introduced or for coloring natural and synthetic resins, such as the Condensation products from formaldehyde and urea, phenols or amines, as well of rubber and polyvinyl compounds can be used.

Aus der deutschen Patentschrift 889 739 ist die Verwendung von Farbstoffen ähnlicher Zusammensetzung zur Herstellung weichmacherfester Färbungen und Drucke bekannt. Der neue Farbstoff ist den in dieser Patentschrift genannten Farbstoffen sowohl hinsichtlich der Lösungsmittel-, Öl- und Überspritzechtheit der damit hergestellten Farblacke als auch in bezug auf die Ausblutechtheit gegenüber Polyvinylchlorid im allgemeinen deutlich überlegen, insbesondere auch dem Farbstoff des Beispiels 4 dieser Patentschrift, den man durch Kuppeln der gleichen Diazoniumverbindung, wie sie im vorliegenden Verfahren verwendet wird, mit 1-(2',3'-Oxynaphthoylamino)-2,4-dimethoxy-5-chlorbenzol erhält.From the German patent specification 889 739 the use of dyes is similar composition for the production of plasticizer-resistant dyeings and prints known. The new dye is one of the dyes mentioned in this patent specification both in terms of the solvent, oil and overspray fastness of the products made with it Color lakes as well as with regard to the bleeding resistance to polyvinyl chloride im generally clearly superior, in particular also to the dye of Example 4 of this patent, which can be obtained by coupling the same diazonium compound as it is used in the present process with 1- (2 ', 3'-oxynaphthoylamino) -2,4-dimethoxy-5-chlorobenzene receives.

Gegenüber dem aus Beispie12 der deutschen Patentschrift 899 538 bekannten, durch Kuppeln der Diazoniumverbindung aus 1-Amino-2-methoxybenzol-5-carbonsäureamid mit 1-(2',3'-Oxynaphthoylamino)-2,5-dimethoxy-4-chlorbenzol erhältlichen Farbstoff zeigt der neue Farbstoff ein wesentlich geringeres Ausbluten der Textilfärbung bei der Wasch- und Superoxydechtheitsprobe. Beispiel 1 12,1 Gewichtsteile 1-Amino-2-methoxybenzol-5-carbonsäure-phenylamid werden in der üblichen Weise diazotiert. Hierauf versetzt man die Diazolösung zur Entfernung der überschüssigen Mineralsäure mit Natriumacetat und rührt sie in eine wäßrige Suspension von 17,9 Gewichtsteilen 1-(2',3'-Oxynaphthoylamino)-2,5-dimethoxy-4-chlorbenzol ein, die man durch Lösen dieser Verbindung in verdünnter Natronlauge und Fällen mit Essigsäure erhält. Der beim Erwärmen auf 40° sich rasch bildende Farbstoff wird nach Beendigung der Kupplung abfiltriert, gut ausgewaschen und getrocknet. Er stellt ein rotes Pulver dar, mit dem man nach einem der gebräuchlichen Verfahren einen Pigmentdruck auf Textilien herstellen kann, etwa unter Verwendung einer Emulsion von Polyvinylacetat und dem wasserlöslichen härtbaren Kondensationsprodukt aus Harnstoff und Formaldehyd. Das erhaltene Druckmuster zeigt einen lebhaften roten Farbton und besitzt gute Echtheitseigenschaften, insbesondere eine sehr gute Lichtechtheit.Compared to that known from Beispie12 of German patent specification 899 538, by coupling the diazonium compound from 1-amino-2-methoxybenzene-5-carboxamide dye obtainable with 1- (2 ', 3'-oxynaphthoylamino) -2,5-dimethoxy-4-chlorobenzene the new dye shows a significantly lower bleeding of the textile dye the wash and superoxide fastness test. Example 1 12.1 parts by weight of 1-amino-2-methoxybenzene-5-carboxylic acid phenylamide are diazotized in the usual way. The diazo solution is then added to the Remove the excess mineral acid with sodium acetate and stir it into a aqueous suspension of 17.9 parts by weight of 1- (2 ', 3'-oxynaphthoylamino) -2,5-dimethoxy-4-chlorobenzene one that can be obtained by dissolving this compound in dilute sodium hydroxide solution and cases obtained with acetic acid. The dye, which forms rapidly when heated to 40 °, is after the coupling has ended, filtered off, washed well and dried. Created is a red powder that can be used to create a Can produce pigment printing on textiles, for example using an emulsion of polyvinyl acetate and the water-soluble, curable condensation product of urea and formaldehyde. The print pattern obtained shows a vivid red hue and has good fastness properties, in particular very good lightfastness.

Verwendet man den Farbstoff zur Herstellung von Farblacken, so erhält man lebhafte blaustichige Rottöne von guter Öl-, Lösungsmittel- und Überspritzechtheit sowie einer sehr guten Lichtechtheit. Man kann dabei die Kupplung auch in Gegenwart eines zur Farblackherstellung geeigneten Trägerstoffes vornehmen.If the dye is used to produce color lakes, then vivid bluish red tones with good oil, solvent and overspray fastness as well as very good lightfastness. You can do the coupling in the presence a carrier material suitable for the production of colored lacquers.

Die mit dem Pigmentfarbstoff durch Einarbeiten in Poly-"rinylchlorid erhältlichen Färbungen besitzen eine sehr gute Ausblutechtheit gegenüber dem ungefärbten Polymerisanonsprodukt und sind sehr lichtecht. Beispiel 2 100 g Baumwollgarn werden 1;'2 Stunde bei 35'- in 21 Grundierungsbad behandelt, abgeschleudert und naß im Entwicklungsbad bei 20° ausgefärbt. Man spült hierauf, seift zunächst bei 60°, dann bei Siedetemperatur und trocknet.Those with the pigment dye by incorporation in poly- "rinyl chloride available dyeings have a very good bleeding resistance compared to the uncolored Polymerisanonsprodukt and are very lightfast. Example 2 100 g of cotton yarn are used 1; '2 hours at 35' - treated in 21 primer bath, spun off and wet in Development bath colored at 20 °. This is followed by rinsing, first soaping at 60 °, then at boiling temperature and dries.

Grundierungsbad 9 gl-(2',3'-Oxynaphthoylamino)-2,5-dimethoxy-4-chlorbenzol werden in 27 ccm vergälltem Alkohol, 3 ccm Natronlauge von 38° B6, 3 ccm Formaldehydlösung (33 °/oig) und 9 ccm warmen Wassers gelöst und mit Wasser von 35°, 10 g Türkischrotöl (50 °/oig) sowie 20 ccm Natronlauge von 38°B6 auf 21 eingestellt.Primer bath 9 gl- (2 ', 3'-oxynaphthoylamino) -2,5-dimethoxy-4-chlorobenzene are in 27 cc denatured alcohol, 3 cc sodium hydroxide solution at 38 ° B6, 3 cc formaldehyde solution (33 ° / oig) and 9 ccm of warm water and with water at 35 °, 10 g Turkish red oil (50%) and 20 ccm sodium hydroxide solution adjusted from 38 ° B6 to 21.

Entwicklungsbad 4,8 g 1-Amino-2-methoxybenzol-5-carbonsäure-phenylamid werden in 30 ccm Wasser mit 9,6 ccm Salzsäure von 15°B6 und 1,6 g in Wasser gelöstem Natriumnitrit unter Kühlung diazotiert; hierauf stellt man unter Zusatz von kaltem Wasser und 20 g Natriumacetat auf 21 ein.Development bath 4.8 g of 1-amino-2-methoxybenzene-5-carboxylic acid phenylamide are dissolved in 30 cc of water with 9.6 cc of hydrochloric acid of 15 ° B6 and 1.6 g of water Sodium nitrite diazotized with cooling; then one places with the addition of cold Water and 20 g sodium acetate to 21.

Man erhält eine lebhafte blaustichigrote Färbung von guter Koch- und Lichtechtheit.A lively bluish-tinged red coloration with good boiling and cooking properties is obtained Lightfastness.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines wasserunlöslichen Monoazofarbstoffes, dadurch gekennzeichnet, daB man die Diazoniumverbindung aus 1-Amino-2-methotybenzol-5-carbonsäure-phenylamid mit 1-(2',3'-Oxynaphthoylamino)-2,5-dimethoxy-4-chlorbenzoI in Substanz, auf der Faser oder auf einem Trägerstoff kuppelt. In Betracht gezogene Druckschriften: Deutsche Patentschrift Nr. 889 739. Bei der Bekanntmachung der Anmeldung sind eine Färbetafel und ein Blatt Erläuterung hierzu ausgelegt «-orden.PATENT CLAIM: Process for the production of a water-insoluble one Monoazo dye, characterized in that one selects the diazonium compound 1-Amino-2-methotybenzene-5-carboxylic acid-phenylamide with 1- (2 ', 3'-oxynaphthoylamino) -2,5-dimethoxy-4-chlorobenzoI in substance, on the fiber or on a carrier material. Considered Publications: German Patent No. 889 739. When the application is published a staining table and a sheet of explanations are laid out «-order.
DEF20827A 1956-07-19 1956-07-19 Process for the preparation of a water-insoluble monoazo dye Pending DE1021105B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF20827A DE1021105B (en) 1956-07-19 1956-07-19 Process for the preparation of a water-insoluble monoazo dye

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF20827A DE1021105B (en) 1956-07-19 1956-07-19 Process for the preparation of a water-insoluble monoazo dye

Publications (1)

Publication Number Publication Date
DE1021105B true DE1021105B (en) 1957-12-19

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DEF20827A Pending DE1021105B (en) 1956-07-19 1956-07-19 Process for the preparation of a water-insoluble monoazo dye

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1291034B (en) * 1962-11-30 1969-03-20 Geigy Ag J R Process for the production of azo pigment dyes
DE1644359B1 (en) * 1966-10-07 1970-11-12 Siegle & Co Gmbh G Process for the preparation of a water-insoluble monoazo dye

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE889739C (en) * 1951-02-15 1953-09-14 Naphtol Chemie Offenbach Process for the production of plasticizer-resistant colors and prints

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE889739C (en) * 1951-02-15 1953-09-14 Naphtol Chemie Offenbach Process for the production of plasticizer-resistant colors and prints

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1291034B (en) * 1962-11-30 1969-03-20 Geigy Ag J R Process for the production of azo pigment dyes
DE1644359B1 (en) * 1966-10-07 1970-11-12 Siegle & Co Gmbh G Process for the preparation of a water-insoluble monoazo dye

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