CH511880A - Basic azo dyestuffs - Google Patents

Basic azo dyestuffs

Info

Publication number
CH511880A
CH511880A CH1177470A CH1177470A CH511880A CH 511880 A CH511880 A CH 511880A CH 1177470 A CH1177470 A CH 1177470A CH 1177470 A CH1177470 A CH 1177470A CH 511880 A CH511880 A CH 511880A
Authority
CH
Switzerland
Prior art keywords
compounds
formula
parts
series
preparation
Prior art date
Application number
CH1177470A
Other languages
German (de)
Inventor
Helmut Dr Moser
Original Assignee
Sandoz Ag
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 Sandoz Ag filed Critical Sandoz Ag
Priority to CH1177470A priority Critical patent/CH511880A/en
Publication of CH511880A publication Critical patent/CH511880A/en

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
    • C09B44/00—Azo dyes containing onium groups
    • C09B44/02—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Coloring (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Paper (AREA)

Abstract

Dyestuffs of formula (I) where X1 is the residue of a coupling component of the amino- or hydroxybenzene series, the heterocyclic series, the amino- or hydroxynaphthalene series or with a methylene group capable of coupling, Y is a direct bond or a divalent bridging group, p is 0-3 A is an anion and K1 is where R' and R" are (subst) alkyl or cycloalkyl or together form a heterocyclic group1 R3 and R4 are H, (substituted) alkyl, cycloalkyl or acyl, R8, R9 and R10 are (substituted) alkyl or cycloalkyl or can make a heterocyclic ring as can R' with R3 and/or R" with R4 are prepared by coupling an amine with a coupling component H-X1-Y-K1 circled positive. The dyestuff may be used for paper and polyacrylonitrile textile material.

Description

  

  
 



  Verfahren zur Herstellung von Verbindungen der Dehydrothiotoluidinreihe
Gegenstand der Erfindung ist ein Verfahren zur Herstellung von Verbindungen der Dihydrothiotoluidinreihe der Formel
EMI1.1     
 worin A den Säurerest eines Esters und n 1 bis 6 bedeuten und die aromatischen Ringe und/oder D weitersubstituiert sein können, dadurch gekennzeichnet.



  dass man eine Verbindung der Formel
EMI1.2     
 nach an sich bekannten Methoden, mit Halogenmethyl abgebenden Verbindungen umsetzt, vorzugsweise chlormethyliert.



   Die Ringe B und/oder D können vorteilhaft durch nicht wasserlöslich machende Substituenten substitiuiert sein.



   Vorzugsweise enthalten sie Halogenatome, die Hydroxy-, Nitro- oder Cyangruppe, gegebenenfalls substituierte Alkyl- oder Alkoxygruppen oder Hydroxyaryloder Alkoxyarylgruppen. Die Verbindungen der Formel (III) können aber auch eine Sulfonsäure- oder Carbonsäuregruppe oder eine Sulfonsäureamid- oder Carbonsäureamidgruppe oder eine Alkyl- oder Arylsulfonylgruppe enthalten.

 

   Die Verbindungen der Formel   (III)    können als Zwischenprodukte für die Herstellung von Farbstoffen verwendet werden.



   Im folgenden Beispiel bedeuten die Teile Gewichtsteile und die Prozente Gewichtsprozente. Die Temperaturen sind in Celsiusgraden angegeben.



   Beispiel
In eine Mischung, bestehend aus 100 Teilen Chlorsulfonsäure und 35 Teilen Schwefelsäure, werden 24 Teile 2-(4'-Amino-phenyl)-6-methyl-benzthiazol und 20 Teilen Paraformaldehyd eingetragen. Das Gemisch wird 10 Stunden lang bei   60     gerührt. Man erhält das chlormethylierte Produkt.



   PATENTANSPRUCH



   Verfahren zur Herstellung von Verbindungen der Dehydrothiotoluidinreihe der Formel
EMI1.3     
 

**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.



   



  
 



  Process for the preparation of compounds of the dehydrothiotoluidine series
The invention relates to a process for the preparation of compounds of the dihydrothiotoluidine series of the formula
EMI1.1
 where A is the acid radical of an ester and n is 1 to 6 and the aromatic rings and / or D can be further substituted, characterized in that.



  that you can get a compound of the formula
EMI1.2
 by methods known per se, reacted with halogenomethyl-releasing compounds, preferably chloromethylated.



   The rings B and / or D can advantageously be substituted by substituents which do not render water soluble.



   They preferably contain halogen atoms, the hydroxyl, nitro or cyano group, optionally substituted alkyl or alkoxy groups or hydroxyaryl or alkoxyaryl groups. The compounds of the formula (III) can, however, also contain a sulfonic acid or carboxylic acid group or a sulfonic acid amide or carboxylic acid amide group or an alkyl or arylsulfonyl group.

 

   The compounds of the formula (III) can be used as intermediates for the preparation of dyes.



   In the following example, parts are parts by weight and percentages are percentages by weight. The temperatures are given in degrees Celsius.



   example
24 parts of 2- (4'-aminophenyl) -6-methyl-benzothiazole and 20 parts of paraformaldehyde are introduced into a mixture consisting of 100 parts of chlorosulfonic acid and 35 parts of sulfuric acid. The mixture is stirred at 60 for 10 hours. The chloromethylated product is obtained.



   PATENT CLAIM



   Process for the preparation of compounds of the dehydrothiotoluidine series of the formula
EMI1.3
 

** WARNING ** End of DESC field could overlap beginning of CLMS **.

Claims (1)

**WARNUNG** Anfang CLMS Feld konnte Ende DESC uberlappen **. ** WARNING ** Beginning of CLMS field could overlap end of DESC **. Verfahren zur Herstellung von Verbindungen der Dehydrothiotoluidinreihe Gegenstand der Erfindung ist ein Verfahren zur Herstellung von Verbindungen der Dihydrothiotoluidinreihe der Formel EMI1.1 worin A den Säurerest eines Esters und n 1 bis 6 bedeuten und die aromatischen Ringe und/oder D weitersubstituiert sein können, dadurch gekennzeichnet. Process for the preparation of compounds of the dehydrothiotoluidine series The invention relates to a process for the preparation of compounds of the dihydrothiotoluidine series of the formula EMI1.1 where A is the acid radical of an ester and n is 1 to 6 and the aromatic rings and / or D can be further substituted, characterized in that. dass man eine Verbindung der Formel EMI1.2 nach an sich bekannten Methoden, mit Halogenmethyl abgebenden Verbindungen umsetzt, vorzugsweise chlormethyliert. that you can get a compound of the formula EMI1.2 by methods known per se, reacted with halogenomethyl-releasing compounds, preferably chloromethylated. Die Ringe B und/oder D können vorteilhaft durch nicht wasserlöslich machende Substituenten substitiuiert sein. The rings B and / or D can advantageously be substituted by substituents which do not render water soluble. Vorzugsweise enthalten sie Halogenatome, die Hydroxy-, Nitro- oder Cyangruppe, gegebenenfalls substituierte Alkyl- oder Alkoxygruppen oder Hydroxyaryloder Alkoxyarylgruppen. Die Verbindungen der Formel (III) können aber auch eine Sulfonsäure- oder Carbonsäuregruppe oder eine Sulfonsäureamid- oder Carbonsäureamidgruppe oder eine Alkyl- oder Arylsulfonylgruppe enthalten. They preferably contain halogen atoms, the hydroxyl, nitro or cyano group, optionally substituted alkyl or alkoxy groups or hydroxyaryl or alkoxyaryl groups. The compounds of the formula (III) can, however, also contain a sulfonic acid or carboxylic acid group or a sulfonic acid amide or carboxylic acid amide group or an alkyl or arylsulfonyl group. Die Verbindungen der Formel (III) können als Zwischenprodukte für die Herstellung von Farbstoffen verwendet werden. The compounds of the formula (III) can be used as intermediates for the preparation of dyes. Im folgenden Beispiel bedeuten die Teile Gewichtsteile und die Prozente Gewichtsprozente. Die Temperaturen sind in Celsiusgraden angegeben. In the following example, parts are parts by weight and percentages are percentages by weight. The temperatures are given in degrees Celsius. Beispiel In eine Mischung, bestehend aus 100 Teilen Chlorsulfonsäure und 35 Teilen Schwefelsäure, werden 24 Teile 2-(4'-Amino-phenyl)-6-methyl-benzthiazol und 20 Teilen Paraformaldehyd eingetragen. Das Gemisch wird 10 Stunden lang bei 60 gerührt. Man erhält das chlormethylierte Produkt. example 24 parts of 2- (4'-aminophenyl) -6-methyl-benzothiazole and 20 parts of paraformaldehyde are introduced into a mixture consisting of 100 parts of chlorosulfonic acid and 35 parts of sulfuric acid. The mixture is stirred at 60 for 10 hours. The chloromethylated product is obtained. PATENTANSPRUCH PATENT CLAIM Verfahren zur Herstellung von Verbindungen der Dehydrothiotoluidinreihe der Formel EMI1.3 worin A den Säurerest eines Esters und n 1 bis 6 bedeuten und die aromatischen Ringe B und/oder D weitersubstituiert sein können, dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI2.1 mit Halogenmethyl abgebenden Verbindungen umsetzt. Process for the preparation of compounds of the dehydrothiotoluidine series of the formula EMI1.3 in which A is the acid radical of an ester and n is 1 to 6 and the aromatic rings B and / or D can be further substituted, characterized in that a compound of the formula EMI2.1 with halomethyl-releasing compounds.
CH1177470A 1968-01-24 1968-01-24 Basic azo dyestuffs CH511880A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CH1177470A CH511880A (en) 1968-01-24 1968-01-24 Basic azo dyestuffs

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH102368A CH513953A (en) 1968-01-24 1968-01-24 Prepn of azo dyes - for textile materials
CH1177470A CH511880A (en) 1968-01-24 1968-01-24 Basic azo dyestuffs

Publications (1)

Publication Number Publication Date
CH511880A true CH511880A (en) 1971-08-31

Family

ID=4200639

Family Applications (4)

Application Number Title Priority Date Filing Date
CH1177470A CH511880A (en) 1968-01-24 1968-01-24 Basic azo dyestuffs
CH474668A CH511879A (en) 1968-01-24 1968-01-24 Basic azo dyestuffs
CH1189270A CH528577A (en) 1968-01-24 1968-01-24 Prepn of azo dyes - for textile materials
CH102368A CH513953A (en) 1968-01-24 1968-01-24 Prepn of azo dyes - for textile materials

Family Applications After (3)

Application Number Title Priority Date Filing Date
CH474668A CH511879A (en) 1968-01-24 1968-01-24 Basic azo dyestuffs
CH1189270A CH528577A (en) 1968-01-24 1968-01-24 Prepn of azo dyes - for textile materials
CH102368A CH513953A (en) 1968-01-24 1968-01-24 Prepn of azo dyes - for textile materials

Country Status (1)

Country Link
CH (4) CH511880A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3066786D1 (en) 1979-02-02 1984-04-12 Ciba Geigy Ag Process for dyeing cellulose-containing fibrous materials

Also Published As

Publication number Publication date
CH528577A (en) 1972-09-30
CH511879A (en) 1971-08-31
CH513953A (en) 1971-10-15

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