DE2158121C3 - Basic oxazine dyes, their preparation and use - Google Patents
Basic oxazine dyes, their preparation and useInfo
- Publication number
- DE2158121C3 DE2158121C3 DE19712158121 DE2158121A DE2158121C3 DE 2158121 C3 DE2158121 C3 DE 2158121C3 DE 19712158121 DE19712158121 DE 19712158121 DE 2158121 A DE2158121 A DE 2158121A DE 2158121 C3 DE2158121 C3 DE 2158121C3
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- dyes
- ethyl
- formula
- carbon atoms
- 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
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
- C09B19/00—Oxazine dyes
Description
2. Farbstoffe gemäß Anspruch 1 der Formel2. Dyestuffs according to Claim 1 of the formula
CH3 CH 3
CH3 CH 3
NHRNHR
Χθ Χ θ
in der R Wasserstoff, Methyl, Äthyl oder Cyanäthyl bedeutet.in which R is hydrogen, methyl, ethyl or cyanoethyl.
3. Ein Verfahren zur Herstellung von Farbstoffen gemäß Anspruch 1 oder 2, dadurch gekennzeichnet, daß man Verbindungen der Formel3. A process for the preparation of dyes according to claim 1 or 2, characterized in that that one compounds of the formula
NONO
in der B Alkyl, vorzugsweise Methyl oder Äthyl, bedeutet, mit Verbindungen der Formel III in which B is alkyl, preferably methyl or ethyl, with compounds of the formula III
CH3 CH 3
HOHO
NHRNHR
umsetzt, wobei R und R1 die im Anspruch 1 angegebene Bedeutung haben.reacts, where R and R 1 have the meaning given in claim 1.
4. Die Verwendung der Farbstoffe gemäß Anspruch 1 und 2 zum Färben von Textilmaterial aus anionisch modifizierten Fasern.4. The use of the dyes according to claim 1 and 2 for dyeing textile material anionically modified fibers.
Die Erfindung betrifft Farbstoffe der Formel IThe invention relates to dyes of the formula I.
CH3 CH 3
NHRNHR
Χθ CH3 Χ θ CH 3
NHRNHR
Χθ Χ θ
Bevorzugte Reste R für Formel Ia sind Wasserstoff, Methyl, Äthyl oder Cyanäthyl.
Die neuen Farbstoffe sind blau und eignen sich zum Färben von anionisch modifizierten Fasern, insbesondere
Acrylnitrilpolymerisaten und Polyestern. Man erhält damit brillante blaue bis grünstichigblaue Färbungen
mit vorzüglichen Echtheiten. Außerdem haben die Farbstoffe eine gute bis sehr gute Wasserlöslichkeit.Preferred radicals R for formula Ia are hydrogen, methyl, ethyl or cyanoethyl.
The new dyes are blue and are suitable for dyeing anionically modified fibers, in particular acrylonitrile polymers and polyesters. This gives brilliant blue to greenish blue dyeings with excellent fastness properties. In addition, the dyes have good to very good solubility in water.
Gegenüber nächstvergleichbaren, aus den bekanntgemachten Unterlagen des belgischen Patents 6 61 783 bekannten Farbstoffen, die gemäß den Angabeil dieser Patentschrift hergestellt wurden, zeichnen sich die erfindungsgemäßen Farbstoffe durch eine sehr viel höhere Farbstärke aus.Compared to the next comparable, from the published documents of the Belgian patent 6 61 783 known dyes which have been prepared in accordance with the information provided in this patent are those according to the invention Dyes are characterized by a much higher color strength.
Zur Herstellung der Farbstoffe der Formel 1 kann man Verbindungen der Formel II To prepare the dyes of the formula 1, compounds of the formula II can be used
in der B Alkyl, vorzugsweise Methyl oder Äthyl, bedeutet, mit Verbindungen der Formel III in which B is alkyl, preferably methyl or ethyl, with compounds of the formula III
CH,CH,
HOHO
NHRNHR
umsetzen. R und R1 haben dabei die angegebenen Bedeutungen. realize. R and R 1 have the meanings given.
Einzelheiten der Umsetzungen sind den folgenden Beispielen zu entnehmen.Details of the reactions can be found in the following examples.
27 g S-Methoxy^-nitrosophenyl-o-tolylammoniumch'iorid werden in 2 Stunden in eine 60° C warme Lösung von 18 g 3-Cyanäthylamino-4-methylphenol und 13 g Zinkchlorid in 100 ml Äthanol eingetragen. Nach einer weiteren Stunde bei 60° C wird die Lösung mit 300 ml Wasser versetzt und die Fällung durch Zugabe von gesättigter Kochsalzlösung vervollständigt. Der Farbstoff ergibt auf Acrylnitrilpolymerisatfasern blaue Färbungen mit sehr guten Echtheiten.27 g of S-methoxy ^ -nitrosophenyl-o-tolylammonium chloride are in 2 hours in a 60 ° C solution of 18 g of 3-cyanoethylamino-4-methylphenol and 13 g Zinc chloride registered in 100 ml of ethanol. After a further hour at 60 ° C, the solution with 300 ml Water is added and the precipitation is completed by adding saturated sodium chloride solution. The dye produces blue dyeings with very good fastness properties on acrylonitrile polymer fibers.
27 g S-Methoxy^-nitrosophenyl-o-tolylammoniumchlorid werden langsam in eine 50° C warme Lösung von 12 g 3-Amino-4-methyiphenol un-i 26 g Zinkch'orid in 100 m) Methanol eingetragen. Der Farbstoff fällt rein als schwerlösliches Zinkchlorid-Doppelsalz aus. Durch Oberführen in das Acetat erhält man einen gut löslichen Farbstoff, der Färbungen mit sehr guten Echtheitseigenschaften ergibt27 g of S-methoxy ^ -nitrosophenyl-o-tolylammonium chloride are slowly poured into a 50 ° C solution of 12 g of 3-amino-4-methyiphenol and 26 g of zinc chloride registered in 100 m) of methanol. The dye precipitates as a sparingly soluble zinc chloride double salt. By When converted into the acetate, a readily soluble dye, the dyeings with very good fastness properties, is obtained results
2525th
27 g S-Methoxy-'t-nitrosophenyl-o-toiylammoniumchlorid werden langsam in eine 80°C warme Lösung von 15 g 3-Äthylamino-4-methylphenol und 13 g Zinkchlorid in 100 ml Methylglykol eingetragen. Der Farbstoff fällt rein als Zinkchlorid-Doppelsalz aus. Er kann leicht über die Base in das gut lösliche Farbstoffchlorid übergeführt werden.27 g of S-methoxy-'t-nitrosophenyl-o-toiylammonium chloride are slowly in a 80 ° C solution of 15 g of 3-ethylamino-4-methylphenol and 13 g of zinc chloride entered in 100 ml of methyl glycol. The dye precipitates as a zinc chloride double salt. He can can easily be converted into the readily soluble dye chloride via the base.
Analog der angegebenen Arbeitsweise erhält man auch die in der folgenden Tabelle durch Angabe der Substituenten charakterisierten blauen Farbstoffe:Analogously to the procedure given, those in the table below are also obtained by specifying the Substituents characterized blue dyes:
CH3 CH 3
I N -
I.
4040
4545
5050
5555
6060
6565
Claims (1)
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19712158121 DE2158121C3 (en) | 1971-11-24 | 1971-11-24 | Basic oxazine dyes, their preparation and use |
CH102272A CH571045A5 (en) | 1971-02-03 | 1972-01-24 | Blue-blue/green oxazine dyes contg arylamine gps - - for faast dyeing polyacrylonitrile,anionically-modified polyesters, |
NL7200948A NL7200948A (en) | 1971-02-03 | 1972-01-24 | |
FR7203107A FR2124306B1 (en) | 1971-02-03 | 1972-01-31 | |
BE778707A BE778707A (en) | 1971-02-03 | 1972-01-31 | PROCESS FOR PREPARING OXAZINIC COLORANTS CONTAINING ARYLAMINE GROUPS AND NEW OXAZINIC COLORANTS |
IT48047/72A IT952020B (en) | 1971-02-03 | 1972-01-31 | PROCEDURE FOR THE PRODUCTION OF BONE DYES WITH ARYLAMINE GROUPS AND DYES OBTAINED |
US00222678A US3828035A (en) | 1971-02-03 | 1972-02-01 | Production of oxazine dyes with arylamino groups |
PL15324572A PL83378B1 (en) | 1971-11-24 | 1972-02-02 | |
JP1146272A JPS5521072B1 (en) | 1971-02-03 | 1972-02-02 | |
GB480572A GB1379165A (en) | 1971-02-03 | 1972-02-02 | Oxazine dyes with an arylamino group |
DD160637A DD95439A5 (en) | 1971-02-03 | 1972-02-02 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19712158121 DE2158121C3 (en) | 1971-11-24 | 1971-11-24 | Basic oxazine dyes, their preparation and use |
Publications (3)
Publication Number | Publication Date |
---|---|
DE2158121A1 DE2158121A1 (en) | 1973-06-07 |
DE2158121B2 DE2158121B2 (en) | 1974-02-14 |
DE2158121C3 true DE2158121C3 (en) | 1984-08-30 |
Family
ID=5825930
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19712158121 Expired DE2158121C3 (en) | 1971-02-03 | 1971-11-24 | Basic oxazine dyes, their preparation and use |
Country Status (2)
Country | Link |
---|---|
DE (1) | DE2158121C3 (en) |
PL (1) | PL83378B1 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3644369A1 (en) * | 1986-12-24 | 1988-07-07 | Basf Ag | METHOD FOR TRANSMITTING CATIONIC DYES IN THEIR DEPROTONED, ELECTRICALLY NEUTRAL FORM |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE661783A (en) * | 1961-09-28 |
-
1971
- 1971-11-24 DE DE19712158121 patent/DE2158121C3/en not_active Expired
-
1972
- 1972-02-02 PL PL15324572A patent/PL83378B1/pl unknown
Also Published As
Publication number | Publication date |
---|---|
PL83378B1 (en) | 1975-12-31 |
DE2158121A1 (en) | 1973-06-07 |
DE2158121B2 (en) | 1974-02-14 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
8281 | Inventor (new situation) |
Free format text: BAUMANN, HANS, DR., 6700 LUDWIGSHAFEN, DE MAYER, UDO, DR., 6710 FRANKENTHAL, DE |
|
C3 | Grant after two publication steps (3rd publication) |