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DE2158121C3 - Basic oxazine dyes, their preparation and use - Google Patents

Basic oxazine dyes, their preparation and use

Info

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
Application number
DE19712158121
Other languages
German (de)
Other versions
DE2158121A1 (en
DE2158121B2 (en
Inventor
Udo Dr. 6710 Frankenthal Mayer
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to DE19712158121 priority Critical patent/DE2158121C3/en
Priority to CH102272A priority patent/CH571045A5/en
Priority to NL7200948A priority patent/NL7200948A/xx
Priority to IT48047/72A priority patent/IT952020B/en
Priority to BE778707A priority patent/BE778707A/en
Priority to FR7203107A priority patent/FR2124306B1/fr
Priority to US00222678A priority patent/US3828035A/en
Priority to DD160637A priority patent/DD95439A5/xx
Priority to GB480572A priority patent/GB1379165A/en
Priority to JP1146272A priority patent/JPS5521072B1/ja
Priority to PL15324572A priority patent/PL83378B1/pl
Publication of DE2158121A1 publication Critical patent/DE2158121A1/en
Publication of DE2158121B2 publication Critical patent/DE2158121B2/en
Application granted granted Critical
Publication of DE2158121C3 publication Critical patent/DE2158121C3/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
    • 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

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.

Beispiel 1example 1

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.

Beispiel 2Example 2

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

Beispiel 3Example 3

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

HH N —
I N -
I. RR. H®H® Beispielexample RR. R1 R 1 44th C2H4OHC 2 H 4 OH P-CH3 P-CH 3 55 CH2CHOHCH3 CH 2 CHOHCH 3 P-CH3 P-CH 3 66th C2H4CIC 2 H 4 CI 0-CH3 0-CH 3 77th C2H4COOCH3C2H4COOCH3 P-CH3 P-CH 3 88th C2H4COOC4H9 C 2 H 4 COOC 4 H 9 P-CH3 P-CH 3 99 HH P-C2H5 PC 2 H 5 1010 HH P-C4H9 PC 4 H 9

4040

4545

5050

5555

6060

6565

Claims (1)

Patentansprüche:Patent claims: 1. Basische Oxazinfarbstoffe der Formel1. Basic oxazine dyes of the formula CH3 CH 3 NHRNHR Χθ Χ θ in derin the in der R Wasserstoff, Alkyl mit 1 bis 4 C-Atomen, Cyanäthyl, Chlc-räthyl, Carbalkoxyäthyl oder Hydroxyalkyl, R1 Alkyl mit 1 bis 4 C-Atomen und Χθ ein Anion bedeu-' teL R is hydrogen, alkyl having 1 to 4 C atoms, cyanoethyl, CHLC räthyl, Carbalkoxyäthyl or hydroxyalkyl, R 1 is alkyl having 1 to 4 carbon atoms and an anion importance Χ θ 'tel Reste R sind außer den schon einzeln genannten z. B.: Propyl, Butyl, Carbomethoxy-, -äthoxy- oder -butoxyäthyl, /-Hydroxyäthyl, /-Hydroxypropyl und vorzugsweise Methyl oder ÄthyLRests are in addition to the individually mentioned z. B .: Propyl, butyl, carbomethoxy, ethoxy or butoxyethyl, / -hydroxyethyl, / -hydroxypropyl and preferably Methyl or ethyl Reste R1 sind z. B. Butyl, Äthyl und insbesondere Methyl. Anionen Χθ sind beispielsweise Chlorid, Bromid, Nitrat, Sulfat, Methosulfat, Athosulfat, Formiat, Acetat, Toluolsulfonat oder TetrachlorozinkaLR 1 radicals are e.g. B. butyl, ethyl and especially methyl. Anions Χ θ are, for example, chloride, bromide, nitrate, sulfate, methosulfate, ethosulfate, formate, acetate, toluenesulfonate or tetrachlorozincal Von besonderer technischer Bedeutung sind Farbstoffe der Formel Ia.Dyes of the formula Ia are of particular industrial importance. Wasserstoff, Alkyl mit 1 bis 4 C-Atomen, Cyan äthyl, Chloräthyl, Carbalkoxyäthyl oder Hy droxyalkyl.Hydrogen, alkyl with 1 to 4 carbon atoms, cyano ethyl, chloroethyl, carbalkoxyethyl or hy hydroxyalkyl. Alkyl mit 1 bis 4 C-Atomen undAlkyl having 1 to 4 carbon atoms and X® ein Anion bedeuten.X® mean an anion.
DE19712158121 1971-02-03 1971-11-24 Basic oxazine dyes, their preparation and use Expired DE2158121C3 (en)

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
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
DD160637A DD95439A5 (en) 1971-02-03 1972-02-02
GB480572A GB1379165A (en) 1971-02-03 1972-02-02 Oxazine dyes with an arylamino group
JP1146272A JPS5521072B1 (en) 1971-02-03 1972-02-02
PL15324572A PL83378B1 (en) 1971-11-24 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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE661783A (en) * 1961-09-28

Also Published As

Publication number Publication date
DE2158121A1 (en) 1973-06-07
DE2158121B2 (en) 1974-02-14
PL83378B1 (en) 1975-12-31

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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)