DE958683C - 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
DE958683C
DE958683C DEF16224A DEF0016224A DE958683C DE 958683 C DE958683 C DE 958683C DE F16224 A DEF16224 A DE F16224A DE F0016224 A DEF0016224 A DE F0016224A DE 958683 C DE958683 C DE 958683C
Authority
DE
Germany
Prior art keywords
water
preparation
monoazo dye
insoluble monoazo
dye
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
DEF16224A
Other languages
German (de)
Inventor
Dr Percy H Fickel
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 DEF16224A priority Critical patent/DE958683C/en
Application granted granted Critical
Publication of DE958683C publication Critical patent/DE958683C/en
Expired 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
    • 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

Landscapes

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

Description

AUSGEGEBEN AM 21. FEBRUAR 1957ISSUED FEBRUARY 21, 1957

F 16224 IVb j 22aF 16224 IVb j 22a

Aus den deutschen Patentschriften 256999, 261 594 und 268 542 ist bekanntgeworden, daß man durch Kuppeln von diazotiertem i-Amino-2-methyl-5-nitröbenzol mit 2, 3-Oxynaphthoylaminobenzol in Substanz oder auf der Faser einen scharlachroten, wasserunlöslichen Monoazofarbstoff erhält, der wegen seines Farbtons erhebliche technische Bedeutung besitzt. Infolge der geringen Substantivität des 2, 3 - Oxynaphthoylaminobenzols zur pflanzlichen Faser war es bisher nur möglich, diesen Farbton auf Garn durch. Färbung auf der Terrine oder Passiermaschine oder, unter höheren Kosten, durch Wamnenfärbung in langen Flottenverhältnissen zu erzeugen, nicht jedoch auf Wickelkörpern, wie Kreuzspulen oder Kettbäumen, sowie auf losem Material auf dem Wege der Apparatefärbung. From German patent specifications 256999, 261 594 and 268 542 has become known that one by coupling diazotized i-amino-2-methyl-5-nitrobenzene with 2,3-oxynaphthoylaminobenzene in substance or on the fiber a scarlet, water-insoluble monoazo dye, which is considerable technical because of its color Has meaning. As a result of the low substantivity of 2, 3 - oxynaphthoylaminobenzene for Until now it was only possible to use vegetable fiber to produce this shade on yarn. Coloring on the Terrine or straining machine or, at higher costs, by dyeing in long liquor ratios to produce, but not on bobbins such as cheeses or warp beams, as well as on loose material by means of apparatus coloring.

Es wurde nun gefunden, daß man zu einem ■wasserunlöslichen Monoazofarbstoff von dem gleichen Farbton gelangt, wenn man diazotiertes ao i-Amino-2-chlor-5-äthylbenzol mit 2-(2', 3'-Oxynaphthoylamino)-naphthalin in Substanz oder auf der Faser vereinigt Mit dem neuen Farbstoff erhält man auf der pflanzlichen Faser farbkräftige Färbungen, die sich gegenüber den unter Verwen- as dung von diazotiertem i-Amino-2-methyl-5-nitrobenzol und 2,3-Oxynaphthoylaminobenzol hergestellten Färbungen durch eine bessere Reib- undIt has now been found that a water-insoluble monoazo dye can be obtained from the same Color is achieved when diazotized ao i-amino-2-chloro-5-ethylbenzene with 2- (2 ', 3'-oxynaphthoylamino) naphthalene in substance or on the fiber combined with the new dye the vegetable fibers are colored with strong colors, which are different from the colors used formation of diazotized i-amino-2-methyl-5-nitrobenzene and 2,3-oxynaphthoylaminobenzene produced dyeings through better friction and

Waschechtheit auszeichnen. Die hohe Substantivität des 2-(ß', 3'-0xynaphthoylamino)-naphthalins erlaubt zudem auch die Herstellung dieses, große technische Bedeutung besitzenden scharlachroten Farbtons auf Wickelkörpern, wie Kreuzspulen oder Kettbäumen, so daß der neue Farbstoff auch in färbetechnischer Hinsicht dem bekannten Farbstoff gegenüber einen erheblichen Fortschritt bedeutet. Gegenüber dem aus der deutschen PatentschriftDistinguish washfastness. The high substantivity of 2- (ß ', 3'-oxynaphthoylamino) -naphthalene also allows the production of this scarlet color, which is of great technical importance, on bobbins such as packages or warp beams, so that the new dye is also the known dye in terms of dyeing technology compared to a significant step forward. Compared to that from the German patent specification

ίο 490 882 bekannten Farbstoff aus diazotierten! i-Amino-2-chl'or-5-methylbenzol und 2-(2', 3'-0xynaphthoylamino) -naphthalin zeichnet sich der erfindungsgemäß erhältliche Farbstoff durch eine bessere Hitzebeständigkeit der Polyvinylchloridfärbungen aus.ίο 490 882 known dye from diazotized! i-Amino-2-chloro-5-methylbenzene and 2- (2 ', 3'-0xynaphthoylamino) -naphthalene, the dye obtainable according to the invention is distinguished by a better heat resistance of the polyvinyl chloride dyeings the end.

Beispielexample

Baumwollgarn wird im Flottenverhältnis 1:20 V2Stunde bei 35° in dem nachfolgenden Grundierungsbade behandelt, abgeschleudert, V2 Stunde im Entwicklungsbad ausgefärbt, gespült, zunächst bei 6o°, dann bei 90° geseift, gespült und getrocknet. Cotton yarn has a liquor ratio of 1:20 V2 hour at 35 ° in the subsequent priming bath treated, spun off, stained for half an hour in the developing bath, rinsed, first Soaped at 60 °, then soaped at 90 °, rinsed and dried.

Grundierungsbad. 1 g 2-(2', 3'-0xynaphthoylamino)-naphthalin wird in 2 ecm denaturiertem Alkohol, ι ecm Wasser, 0,4 ecm Natronlauge von 380 Be und 0,5 ecm Formaldehydlösung (33°/oig) gelöst und mit Wasser, 10 ecm Natronlauge von 380 Be und 5 ecm Natron-Türkischrotöl (5o°/oig) auf 11 eingestellt.Primer bath. 1 g of 2- (2 ', 3'-0xynaphthoylamino) naphthalene is dissolved in 2 ecm denatured alcohol, ι ecm water, 0.4 ecm sodium hydroxide solution of 38 0 Be and 0.5 ecm formaldehyde solution (33%) and with Water, 10 ecm sodium hydroxide solution of 38 0 Be and 5 ecm sodium Turkish red oil (50%) adjusted to 11.

Entwicklungsbad. 1,92 g 1 - Amino - 2 - chlor-5-äthylbenzol-hydrochlorid werden mit etwas Wasser und 0,5 ecm einer 3o°/odgen Lösung eines Einwirkungsproduktes von etwa 30 Mol Äthylenoxyd auf Octadecylalkohol gelöst und mit 2,1 ecm Salzsäure von 200 Be und 0,8 g Natriumnitrit, gelöst in etwas Wasser, diazotiert.Developing bath. 1.92 g of 1 - amino - 2 - chloro-5-ethylbenzene hydrochloride are dissolved with a little water and 0.5 ecm of a 3o ° / odgen solution of an action product of about 30 moles of ethylene oxide on octadecyl alcohol and with 2.1 ecm of hydrochloric acid 20 0 Be and 0.8 g of sodium nitrite, dissolved in a little water, diazotized.

Nach beendeter Diazotierung wird mit Wasser verdünnt und nach Zugabe von 1 ecm Essigsäure (500Mg) und 10 g Natriumacetat mit Wasser auf 11 eingestellt.After completion of the diazotization is diluted with water, and (50 0 mg) and 10 g of sodium acetate with water adjusted to 11 by addition of 1 cc of acetic acid.

Man erhält ein Scharlach von guten Echtheitseigenschaften. A scarlet with good fastness properties is obtained.

Der Farbstoff kann auch auf regenerierten Gellulosefasern, beispielsweise Viskose oder Zeilwolle, sowie in Substanz hergestellt werden.The dye can also be applied to regenerated cellulose fibers, for example viscose or linen wool, as well as in substance.

Claims (1)

PATENTANSPRUCH:PATENT CLAIM: Verfahren zur Herstellung eines wasserunlöslichen Monoazofarbstoffe, dadurch gekennzeichnet, daß man diazotiertes i-Amino-2-chlor-5-äthylbenzol mit 2-(2', 3'-Oxynaphthoylamino)-naphthalin, in Substanz oder auf der Faser vereinigt.Process for the preparation of a water-insoluble monoazo dye, characterized in that that one diazotized i-amino-2-chloro-5-ethylbenzene with 2- (2 ', 3'-oxynaphthoylamino) naphthalene, combined in substance or on the fiber. In Betracht gezogene Druckschriften,:
Deutsche Patentschriften Nr. 490 882, 500 175.Considered publications:
German patent specifications No. 490 882, 500 175. © 609 580/421 8.56 (609 802 2.57)© 609 580/421 8.56 (609 802 2.57)
DEF16224A 1954-11-26 1954-11-26 Process for the preparation of a water-insoluble monoazo dye Expired DE958683C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF16224A DE958683C (en) 1954-11-26 1954-11-26 Process for the preparation of a water-insoluble monoazo dye

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF16224A DE958683C (en) 1954-11-26 1954-11-26 Process for the preparation of a water-insoluble monoazo dye

Publications (1)

Publication Number Publication Date
DE958683C true DE958683C (en) 1957-02-21

Family

ID=7088144

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF16224A Expired DE958683C (en) 1954-11-26 1954-11-26 Process for the preparation of a water-insoluble monoazo dye

Country Status (1)

Country Link
DE (1) DE958683C (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1163285B (en) * 1957-06-05 1964-02-20 Cassella Farbwerke Mainkur Ag Process for the production of ice colors on textile goods made of polyesters, in particular polyethylene glycol terephthalates
DE1644385B1 (en) * 1965-10-14 1971-07-08 Sterling Drug Inc Process for the preparation of a water-insoluble monoazo dye

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE490882C (en) * 1925-04-19 1930-02-03 I G Farbenindustrie Akt Ges Process for the preparation of water-insoluble azo dyes
DE500175C (en) * 1927-08-09 1930-06-18 I G Farbenindustrie Akt Ges Process for the production of azo dyes

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE490882C (en) * 1925-04-19 1930-02-03 I G Farbenindustrie Akt Ges Process for the preparation of water-insoluble azo dyes
DE500175C (en) * 1927-08-09 1930-06-18 I G Farbenindustrie Akt Ges Process for the production of azo dyes

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1163285B (en) * 1957-06-05 1964-02-20 Cassella Farbwerke Mainkur Ag Process for the production of ice colors on textile goods made of polyesters, in particular polyethylene glycol terephthalates
DE1644385B1 (en) * 1965-10-14 1971-07-08 Sterling Drug Inc Process for the preparation of a water-insoluble monoazo dye

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