DE2158121A1 - Blue-blue/green oxazine dyes contg arylamine gps - - for faast dyeing polyacrylonitrile,anionically-modified polyesters, - Google Patents

Blue-blue/green oxazine dyes contg arylamine gps - - for faast dyeing polyacrylonitrile,anionically-modified polyesters,

Info

Publication number
DE2158121A1
DE2158121A1 DE19712158121 DE2158121A DE2158121A1 DE 2158121 A1 DE2158121 A1 DE 2158121A1 DE 19712158121 DE19712158121 DE 19712158121 DE 2158121 A DE2158121 A DE 2158121A DE 2158121 A1 DE2158121 A1 DE 2158121A1
Authority
DE
Germany
Prior art keywords
blue
alkyl
formula
anionically
faast
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
DE2158121B2 (en
DE2158121C3 (en
Inventor
Hans Dr Baumann
Udo Dr 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 NL7200948A priority patent/NL7200948A/xx
Priority to CH102272A priority patent/CH571045A5/en
Priority to FR7203107A priority patent/FR2124306B1/fr
Priority to IT48047/72A priority patent/IT952020B/en
Priority to BE778707A priority patent/BE778707A/en
Priority to US00222678A priority patent/US3828035A/en
Priority to GB480572A priority patent/GB1379165A/en
Priority to PL15324572A priority patent/PL83378B1/pl
Priority to DD160637A priority patent/DD95439A5/xx
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

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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)
  • Pyridine Compounds (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)

Abstract

Dyes of formula (I) (where A1 is H, alkyl, cycloalkyl, aralkyl or opt. substd. aryl; A2 is H or opt. substd. alkyl; A3 is H or 1-4C alkyl; A4 is H or 1-4C alkyl opt. substd. by Cl, OH, carbalkoxy or cyano gp; A5 is H, or 1-4C alkyl or alkoxy; Z is an anion) are prepd. by condensing cpds. of formula (II):- with cpds. of formula (III):- (where A6 is 1-4C alkyl), pref. in a polar solvent at 20-110 degrees C, esp. 40-80 degrees C, in the presence of an acid.

Description

Basische Oxazinfarbstoffe Die Erfindung betrifft Farbstoffe der Formel I in der R Wasserstoff, Alkyl mit 1 bis 4 C-Atomen, CyanEthyl, Chloräthyl, Carbalkoxyäthyl oder Hydroxyalkyl, R1 Wasserstoff, Methyl oder Äthyl, R2 Wasserstoff, Alkyl mit 1 bis 4 C-Atomen, Mydroxyalkyl, Carbalkoxyäthyl, Cyanäthyl oder Chloräthyl, R3 Alkyl mit 1 bis 4 C-Atomen und ein Anion bedeuten.Basic Oxazine Dyes The invention relates to dyes of the formula I in which R is hydrogen, alkyl with 1 to 4 carbon atoms, cyanoethyl, chloroethyl, carbalkoxyethyl or hydroxyalkyl, R1 is hydrogen, methyl or ethyl, R2 is hydrogen, alkyl with 1 to 4 carbon atoms, hydroxyalkyl, carbalkoxyethyl, cyanoethyl or chloroethyl, R3 Mean alkyl having 1 to 4 carbon atoms and an anion.

Reste R und R2 sind außer den schon einzeln genannten z. B.: Propyl, Butyl, Carbomethoxy-,- -äthoxy- oder -butoxyäthyl, ß-Hydroxyäthyl, 8-Hydroxypropyl und vorzugsweise Methyl oder Äthyl.R and R2 are apart from those already mentioned individually, for. E.g .: propyl, Butyl, carbomethoxy, ethoxy or butoxyethyl, β-hydroxyethyl, 8-hydroxypropyl and preferably methyl or ethyl.

Reste R3 sind z. B. Butyl, Äthyl und insbesondere Methyl.R3 radicals are e.g. B. butyl, ethyl and especially methyl.

Anionen X@ sind beispielsweise Chlorid, Bromid, Nitrat, Sulfat, Methosulfat, Äthosulfat, Formiat, Acetat, Toluolsulfonat oder Tetrachlorozinkat.Anions X @ are, for example, chloride, bromide, nitrate, sulfate, methosulfate, Ethosulfate, formate, acetate, toluenesulfonate or tetrachlorozincate.

Von besonderer technischer Bedeutung sind Farbstoffe der Formel Ia Bevorzugte Reste R für Formel Ia sind Wasserstoff, Methyl, Äthyl oder Cyanat-hyl.Dyes of the formula Ia are of particular industrial importance Preferred radicals R for formula Ia are hydrogen, methyl, ethyl or cyanate-hyl.

Die neuen Farbstoffe sind blau und eignen sich zum Färben von anionisch modifizierten Fasern, insbesondere Acrylnitrilpolymerisaten und Polyestern. Man erhält damit brillante blaue bis grünstichig blaue Färbungen mit vorzüglichen Echtheiten.The new dyes are blue and are suitable for dyeing anionic modified fibers, especially acrylonitrile polymers and polyesters. Man thus obtains brilliant blue to greenish blue dyeings with excellent fastness properties.

Außerdem haben die Farbstoffe eine gute bis sehr gute Wasserlöslichkeit Zur Herstellung der Farbstoffe der Formel I kann man Verbindungen der Formel II in der B Alkyl, vorzugsweise Methyl oder Äthyl, bedeutet, mit Verbindungen der Formel III 2 umsetzen. R, R1, R und R3 haben dabei die angegebenen Bedeutungen.In addition, the dyes have good to very good solubility in water. For the preparation of the dyes of the formula I, compounds of the formula II can be used in which B is alkyl, preferably methyl or ethyl, with compounds of the formula III 2 implement. R, R1, R and R3 have the meanings given.

Einzelheiten der Umsetzungen sind denfolgenden Beispielen zu entnehmen.Details of the conversions can be found in the following examples.

Beispiel 1 27 g 3-Methoxy-4-nitrosophenyl-o-tolylammoniumchlorid werden in zwei 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. Example 1 27 g of 3-methoxy-4-nitrosophenyl-o-tolylammonium chloride are in two hours in a 60 ° C solution of 18 g of 3-cyanoethylamino-4-methylphenol and added 13 g of zinc chloride in 100 ml of ethanol. After another hour at 60 ° C, the solution is mixed with 300 ml of water and the precipitation by adding saturated saline solution.

Der Farbstoff ergibt auf Acrylnitrilpolymerisatfasern blaue Färbungen mit sehr guten Echtheiten.The dye produces blue dyeings on acrylonitrile polymer fibers with very good fastness properties.

Beispiel 2 27 g 3-Methoxy-4-nitrosophenyl-o-tolylammoniumchlorid werden langsam in eine 50 oC warme Lösung von 12 g 3-Amino-4-methylphenol und 26 g Zinkchlorid in 100 ml Methanol eingetragen. Example 2 27 g of 3-methoxy-4-nitrosophenyl-o-tolylammonium chloride are slowly poured into a 50 oC solution of 12 g of 3-amino-4-methylphenol and Entered 26 g of zinc chloride in 100 ml of methanol.

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.The dye falls in the form of a sparingly soluble zinc chloride double salt By converting it into the acetate, a readily soluble dye is obtained, the Dyeings with very good fastness properties results.

Beispiel 3 27 g 3-Methoxy-4-nitrosophenyl-o-tolylammoniumchlorid 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 Farbstoff@hlorid übergeführt werden. Example 3 27 g of 3-methoxy-4-nitrosophenyl-o-tolylammonium chloride are slowly in a 80 ° C solution of 15 g of 3-ethylamino-4-methylphenol and 13 g of zinc chloride added to 100 ml of methyl glycol. The dye falls pure as Zinc chloride double salt. It can easily be converted into the readily soluble dye @chloride via the base be transferred.

Analog der angegebenen Arbeitsweise erhält man auch die in der folgenden Tabelle durch Angabe der Substituenten charakterisierten blauen Farbstoffe: Beisp. R R1 R2 R3 4 C4H9 H H o-CH3 5 C2H4OH CH3 H p-CH3 6 CH2CHOHCH3 CH3 H p-CH3 7 C2H4Cl CH3 H o-CH3 8 C2H4COOCH3 CH3 H p-CH3 9 C2H4COOC4H9 CH3 H p-CH3 10 CH3 C2H5 H o-CH3 11 H CH3 CH3 p-CH3 12 C2H5 CH3 C4H9 p-CH3 13 C2H5 CH3 C2H4OH p-CH3 14 C2H5 CH3 CH2CHOHCH p-CH3 15 C2H5 CH3 C2H4COOC2H5 p-CH3 16 C2H5 CH3 C2H4CN p-CH3 17 C2H5 CH3 C2H4Cl p-CH3 18 H CH3 H p-C2H5 19 H CH3 II p-C4H9The blue dyes characterized in the following table by specifying the substituents are also obtained analogously to the procedure given: Ex. R R1 R2 R3 4 C4H9 HH o-CH3 5 C2H4OH CH3 H p-CH3 6 CH2CHOHCH3 CH3 H p-CH3 7 C2H4Cl CH3 H o-CH3 8 C2H4COOCH3 CH3 H p-CH3 9 C2H4COOC4H9 CH3 H p-CH3 10 CH3 C2H5 H o-CH3 11 H CH3 CH3 p-CH3 12 C2H5 CH3 C4H9 p-CH3 13 C2H5 CH3 C2H4OH p-CH3 14 C2H5 CH3 CH2CHOHCH p-CH3 15 C2H5 CH3 C2H4COOC2H5 p-CH3 16 C2H5 CH3 C2H4CN p-CH3 17 C2H5 CH3 C2H4Cl5 CH3 p-CH3 18 H CH3 H p-C2H5 19 H CH3 II p-C4H9

Claims (4)

Patentansprüche 1. Basische Oxazinfarbstoffe der Formel in der R Wasserstoff, Alkyl mit 1 bis 4 C-Atomen, Cyanethyl, Chloräthyl, Carbalkoxyäthyl oder Hydroxyalkyl, R1 Wasserstoff, Methyl oder Äthyl, R2 Wasserstoff, Alkyl mit 1 bis 4 C-Atomen, Hydroxyalkyl, Carbalkoxyäthyl, cyanäthyl oder Chloräthyl, R3 Alkyl mit 1 bis 4 C-Atomen und ein Anion bedeuten.Claims 1. Basic oxazine dyes of the formula in which R is hydrogen, alkyl with 1 to 4 carbon atoms, cyanoethyl, chloroethyl, carbalkoxyethyl or hydroxyalkyl, R1 is hydrogen, methyl or ethyl, R2 is hydrogen, alkyl with 1 to 4 carbon atoms, hydroxyalkyl, carbalkoxyethyl, cyanoethyl or chloroethyl, R3 Mean alkyl having 1 to 4 carbon atoms and an anion. 2. Farbstoffe gemäß Anspruch 1 der Formel in der R Wasserstoff, Methyl, Äthyl oder Cyanäthyl bedeutet.2. Dyestuffs according to Claim 1 of the formula in which R is hydrogen, methyl, ethyl or cyanoethyl. 3. Die Verwendung der Farbstoffe gemäß Anspruch 1 und 2 zum Färben von Textilmaterial aus anionisch modifizierten Fasern.3. The use of the dyes according to claim 1 and 2 for dyeing of textile material made from anionically modified fibers. 4. Sir. Verfahren zur Herstellung von Farbstoffen gemäß Anspruch 1 oder 2, dadurch gekennzeichnet, daß man Vebbindungen der Formel in der B Alkyl, vorzugsweise Methyl oder Äthyl, bedeutet, mit Verbindungen der Formel III umsetzt.4. Sir. Process for the preparation of dyes according to Claim 1 or 2, characterized in that compounds of the formula in which B is alkyl, preferably methyl or ethyl, with compounds of the formula III implements.
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
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,
IT48047/72A IT952020B (en) 1971-02-03 1972-01-31 PROCEDURE FOR THE PRODUCTION OF BONE DYES WITH ARYLAMINE GROUPS AND DYES OBTAINED
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
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)

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DE2158121A1 true DE2158121A1 (en) 1973-06-07
DE2158121B2 DE2158121B2 (en) 1974-02-14
DE2158121C3 DE2158121C3 (en) 1984-08-30

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DE19712158121 Expired DE2158121C3 (en) 1971-02-03 1971-11-24 Basic oxazine dyes, their preparation and use

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PL (1) PL83378B1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4880769A (en) * 1986-12-24 1989-11-14 Basf Aktiengesellschaft Transfer of catinic dyes in their deprotonated, electrically neutral form

Citations (1)

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

Patent Citations (1)

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

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Bei der Bekanntmachung der Anmeldung sind drei mit Erläuterungen versehene Färbetafeln ausgelegt worden

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4880769A (en) * 1986-12-24 1989-11-14 Basf Aktiengesellschaft Transfer of catinic dyes in their deprotonated, electrically neutral form

Also Published As

Publication number Publication date
PL83378B1 (en) 1975-12-31
DE2158121B2 (en) 1974-02-14
DE2158121C3 (en) 1984-08-30

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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)