DE2158121B2 - Basic oxazine dyes, their preparation and use - Google Patents

Basic oxazine dyes, their preparation and use

Info

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
Application number
DE19712158121
Other languages
German (de)
Other versions
DE2158121A1 (en
DE2158121C3 (en
Inventor
Hans Dr. 6700 Ludwigshafen Baumann
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 FR7203107A priority patent/FR2124306B1/fr
Priority to BE778707A priority patent/BE778707A/en
Priority to US00222678A priority patent/US3828035A/en
Priority to DD160637A priority patent/DD95439A5/xx
Priority to GB480572A priority patent/GB1379165A/en
Priority to PL15324572A priority patent/PL83378B1/pl
Priority to JP1146272A priority patent/JPS5521072B1/ja
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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (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

Beispiel 2 icExample 2 ic

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.

Beispiel 3Example 3

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.

Beispielexample RR. R'R ' HH R1 R 1 44th C2H4OHC 2 H 4 OH HH P-CH3 P-CH 3 55 CH2CHOHCH3 CH 2 CHOHCH 3 HH P-CH3 P-CH 3 66th C2H4ClC 2 H 4 Cl HH o»CH3 o »CH 3 77th C2H4COOCH3 C 2 H 4 COOCH 3 HH P-CH3 P-CH 3 88th C2H4COOC4H9 C 2 H 4 COOC 4 H 9 CH3 CH 3 P-CH3 P-CH 3 99 HH QH9 QH 9 P-CH3 P-CH 3 1010 QH5 QH 5 C2H4OHC 2 H 4 OH P-CH3 P-CH 3 1111 QH5 QH 5 CH2CHOHCH3 CH 2 CHOHCH 3 P-CH3 P-CH 3 1212th QH5 QH 5 C2H4COOQH5 C 2 H 4 COOQH 5 P-CH3 P-CH 3 1313th C2H5 C 2 H 5 C2H4CNC 2 H 4 CN P-CH3 P-CH 3 1414th QH5 QH 5 C2H4ClC 2 H 4 Cl P-CH3 P-CH 3 1515th QH5 QH 5 HH P-CH3 P-CH 3 1616 HH HH P-C2H5 PC 2 H 5 1717th HH P-C4H9 PC 4 H 9

Claims (2)

22 ·. Patentansprüche: 1, Basische Oxazinfarbstoffe der Formel ·. Claims: 1, basic oxazine dyes of the formula NHRNHR 1010 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, Carbalkoxyäthyl, Cyanäthyl oder Chloräthyl, R2 Alkyl mit 1 bis 4 C-Atomen und Xe ein Anion bedeutet.in 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, carbalkoxyethyl, cyanoethyl or chloroethyl, R 2 is alkyl with 1 to 4 C atoms and X e means an anion. 2. Farbstoffe gemäß Anspruch 1 der Formel2. Dyestuffs according to Claim 1 of the formula Chloräthyi, R2 Alkyl mit J bis 4C-Atoraen unü Xe ein Anion bedeutet,Chloräthyi, R 2 alkyl with J to 4C atoms and X e means an anion, Reste R und Rv sind außer den schon einzeln genannten z, B.: PropyL Butyl. Carbometboxy-, -ätboxy- oder -butoxyäthyi, /3-Hydruxyäthyi, /3-Hydroxypropy) und vorzugsweise Methyl öder Äthyl.In addition to those already mentioned individually, R and R v are, for example: PropyL butyl. Carbometboxy-, -ätboxy- or -butoxyäthyi, / 3-Hydroxyäthyi, / 3-Hydroxypropy) and preferably methyl or ethyl. Reste R sind z. B. Butyl, Äthyl uad insbesondere Methyl. Anionen Χθ sind beispielsweise Chlorid, Bromid, Nitrat, Sulfat, Metbosulfat, Äthosulfat, Formiat, Acetat, Toluolsulfonat oder Teirachlorozinkat.Remainders R are z. B. butyl, ethyl uad especially methyl. Anions Χ θ are, for example, chloride, bromide, nitrate, sulfate, metbosulfate, ethosulfate, formate, acetate, toluenesulfonate or teirachlorozincate. Von besonderer technischer Bedeutung sind Farbstoffe der Formel Ia.Dyes of the formula Ia are of particular industrial importance.
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
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
DD160637A DD95439A5 (en) 1971-02-03 1972-02-02
GB480572A GB1379165A (en) 1971-02-03 1972-02-02 Oxazine dyes with an arylamino group
PL15324572A PL83378B1 (en) 1971-11-24 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)

* 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
PL83378B1 (en) 1975-12-31
DE2158121A1 (en) 1973-06-07
DE2158121C3 (en) 1984-08-30

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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)