DE2158121B2 - Basic oxazine dyes, their preparation and use - Google Patents
Basic oxazine dyes, their preparation and useInfo
- Publication number
- DE2158121B2 DE2158121B2 DE19712158121 DE2158121A DE2158121B2 DE 2158121 B2 DE2158121 B2 DE 2158121B2 DE 19712158121 DE19712158121 DE 19712158121 DE 2158121 A DE2158121 A DE 2158121A DE 2158121 B2 DE2158121 B2 DE 2158121B2
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- formula
- dyes
- ethyl
- hydrogen
- 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.)
- Granted
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Description
Χθ (Ia)Χ θ (Ia)
in der R Wasserstoff, Methyl, Äthyl oder Cyanithyl bedeutet.in which R is hydrogen, methyl, ethyl or cyanithyl.
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 Alkyi, vorzugsweise Methyl oder Äthyl, bedeutet, mit Verbindungen der Formel IIIin which B is alkyl, preferably methyl or ethyl, with compounds of the formula III
CH3 CH 3
Bevorzugte Reste R für Formel Ia sind Wasserstoff, Methyl, Äthyl oder Cyanäthyl.Preferred radicals R for formula Ia are hydrogen, methyl, ethyl or cyanoethyl.
Die neuen Farbstoffe sind blau und eignen sich zum Färben von anionisch modifizierten Fasern,The new dyes are blue and are suitable for dyeing anionically modified fibers,
insbesondere Acrylnitrilpolymerisaten und Polyestern.in particular acrylonitrile polymers and polyesters.
Man erhält damit brillante blaue bis grünstichigblaue Färbungen mit vorzüglichen Echtheiten. Außerdem haben die Farbstoffe eine gute bis sehr gute Wasserlöslichkeit. This gives brilliant blue to greenish blue dyeings with excellent fastness properties. aside from that the dyes have good to very good water solubility.
Gegenüber nächstvergleichbaren, aus den bekanntgemachten Unterlagen des belgischen Patents 661 783 bekannten Farbstoffen, die gemäß den Angaben 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 661 783 known dyes, which were prepared according to the information in this patent, are characterized by the Dyes according to the invention are characterized by a much higher color strength.
Zur Herstellung der Farbstoffe der Formel I kann man Verbindungen der Formel IITo prepare the dyes of the formula I, compounds of the formula II can be used
4040
HOHO
R2 R 2
NHRNHR
R1 R 1
NONO
OBIF
(H)(H)
umsetzt, wobei R, R1 und R2 die im Anspruch 1 angegebene Bedeutung haben.reacted, where R, R 1 and R 2 have the meaning given in claim 1.
4. Die Verwendung der Farbstoffe gemäß Anepruch 1 und 2 zum Färben von Textilmaterial aus anionisch modifizierten Fasern.4. The use of the dyes according to Anepruch 1 and 2 for dyeing textile material anionically modified fibers.
in der B Alkyl, vorzugsweise Mechyl oder Äthyl, bedeutet, mit Verbindungen der Formel HIin which B is alkyl, preferably mechyl or ethyl, with compounds of the formula HI
55 HO 55 HO
CH3 CH 3
NHRNHR
(III)(III)
Die Erfindung betrifft Farbstoffe der FormelThe invention relates to dyes of the formula
NHRNHR
Χθ Χ θ
(D(D
umsetzen. R, R1 und R2 haben dabei die angegebenen Bedeutungen.realize. R, R 1 and R 2 have the meanings given.
Einzelheiten der Umsetzungen sind den folgenden Beispielen zu entnehmen.Details of the reactions can be found in the following examples.
in der R Wasserstoff, Alkyl mit 1 bis 4 C-Atomen, Cyanäthyl, Chloräthyl, Carbalkoxyäthyl oder Hydroxyalkyl, R1 Wasserstoff, Alkyl mit 1 bis 4 C-Atomen, Hydroxyalkyl, Carbalkoxyäthjl, Cyanäthyl oder Beispiet 1in which R is hydrogen, alkyl with 1 to 4 carbon atoms, cyanoethyl, chloroethyl, carbalkoxyethyl or hydroxyalkyl, R 1 is hydrogen, alkyl with 1 to 4 carbon atoms, hydroxyalkyl, carbalkoxyäthjl, cyanoethyl or example 1
27 g 3 - Methoxy - 4 - nitrosophenyl - ο - tolylammoniumchlorid werden in 2 Stunden in eine 6O0C warme27 g of 3 - methoxy - 4 - nitrosophenyl - ο - tolylammonium chloride are placed in a 6O 0 C warm in 2 hours
Lösung von 13 g yyyp
und 13 g ZinkcWorid m IQG ml Äthanol eingetragen.
Nach einer weitere» Stunde bei (ffC wird die Lösung
mit 300 roi Wawer versetzt und die Fällung durch
Zugabe von gesättigter Kochsalzlösung vervollständigt.
Der Farbstaft ergibt auf Äcrylnitrilpolymerisatfasern
blaue Färbungen mit sehr guten Echtheiten. Analog der angegebenen Arbeitsweise erhält man
auch die in der folgenden Tabelle durch Angabe der Substituenten charakterisierten blaue» Farbstoffe:Solution of 13 g yyyp
and 13 g of ZinkcWorid were added to IQG ml of ethanol. After a further hour at (ff C., 300 roi Wawer are added to the solution and the precipitation is completed by adding saturated sodium chloride solution. The dye gives blue dyeings with very good fastness properties on acrylonitrile polymer fibers. The procedure given in the following is also obtained by analogy with the procedure given Table characterized by the indication of the substituents blue »dyes:
Ny^yCH3 Ny ^ yCH 3
27 g 3 - Methoxy - 4 - nitrosophenyl - ο - tolylammoniumchlorid werden langsam in eine 500C warme Lösung von 12 g 3-Amino-4-metbylphenol und 26 g Zinkchlorid in 100 ml Methanol eingetragen Der Farbstoff fällt rein als schwerlösliches Zinkchlorid-Doppelsalz aus. Durch überführen in das Acetat erhält man einen gut löslichen Farbstoff, der Färbungen mit sehr guten Echtheitseigenschaften ergibt.27 g 3 - methoxy - 4 - nitrosophenyl - ο - tolylammoniumchlorid slowly in a 50 0 C warm solution of 12 g of 3-amino-4-metbylphenol and added 26 g of zinc chloride in 100 ml of methanol The dye precipitates purely as a sparingly soluble zinc chloride double salt the end. By converting it into the acetate, a readily soluble dye is obtained which gives dyeings with very good fastness properties.
27 g 3 - Methoxy - 4 - nitrosophenyl - ο - tolylammoniumchlorid werden langsam in eine 8O0C warme Lösung von 15g 3-Äthylamino-4-methylphenol und 13 g Zinkchlorid in 100 ml Methylglykol eingetragen. Der Farbstoff lallt rein als Zinkchlorid-Doppelsalz aus. Er kann leicht über die Base in das gut lösliche Far! Stoffchlorid übergeführt werden.27 g 3 - methoxy - 4 - nitrosophenyl - ο - tolylammoniumchlorid slowly warm in a 8O 0 C solution are added 15g of 3-ethylamino-4-methylphenol and 13 g of zinc chloride in 100 ml of methylene glycol. The dye lalls out as a zinc chloride double salt. It can easily be converted into the readily soluble Far! Substance chloride are transferred.
Claims (2)
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 |
NL7200948A NL7200948A (en) | 1971-02-03 | 1972-01-24 | |
CH102272A CH571045A5 (en) | 1971-02-03 | 1972-01-24 | Blue-blue/green oxazine dyes contg arylamine gps - - for faast dyeing polyacrylonitrile,anionically-modified polyesters, |
BE778707A BE778707A (en) | 1971-02-03 | 1972-01-31 | PROCESS FOR PREPARING OXAZINIC COLORANTS CONTAINING ARYLAMINE GROUPS AND NEW OXAZINIC COLORANTS |
FR7203107A FR2124306B1 (en) | 1971-02-03 | 1972-01-31 | |
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 |
GB480572A GB1379165A (en) | 1971-02-03 | 1972-02-02 | Oxazine dyes with an arylamino group |
PL15324572A PL83378B1 (en) | 1971-11-24 | 1972-02-02 | |
DD160637A DD95439A5 (en) | 1971-02-03 | 1972-02-02 | |
JP1146272A JPS5521072B1 (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 true DE2158121B2 (en) | 1974-02-14 |
DE2158121C3 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 |
---|---|
DE2158121C3 (en) | 1984-08-30 |
PL83378B1 (en) | 1975-12-31 |
DE2158121A1 (en) | 1973-06-07 |
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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) |