Patent GB-945820-A (GB)
Title: New diazapolymethine dyes
Inventor: DEHNERT JOHANNES
IPC: C09B44/10
Filed: 1961-04-05
Abstract: The invention comprises dyes of the general formula <FORM:0945820/C3/1> wherein the moieties <FORM:0945820/C3/2> and <FORM:0945820/C3/3> denote the radicals of five- or six-membered nitrogenous rings which may be substituted and/or condensed with one or more benzene rings, R denotes a hydrogen atom or a substituted or unsubstituted alkyl, cycloalkyl, aryl or aralkyl group, R1 and R11 each represent a substituted or unsubstituted alkyl or aralkyl group, X represents an anion and m and n represent 0 or 1 and processes for the preparation thereof wherein (a) a hydrazone of the formula <FORM:0945820/C3/4> in which the group <FORM:0945820/C3/5> denotes a radical of a 5- or 6-membered heterocyclic ring which may be substituted and/or condensed with one or more benzene rings and R denotes a hydrogen atom or a hydrocarbon radical, or a salt of such a hydrazone is coupled in the presence of a dehydrogenating or oxidizing agent with a compound of the formula <FORM:0945820/C3/6> in which the groups <FORM:0945820/C3/7> denote identical or different five- or six-membered heterocyclic rings which may bear further substituents or condensed-on benzene rings, or with a derivative thereof alkylated on a nitrogen atom and if desired the product is reacted with an alkylating agent or (b) an amine of the formula <FORM:0945820/C3/8> in which the group <FORM:0945820/C3/9> denotes the radical of a 5- or 6-membered heterocyclic ring which may be substituted and/or condensed with one or more benzene rings is diazotized, the resultant diazonium compound is coupled with a compound of the formula <FORM:0945820/C3/10> in which the groups <FORM:0945820/C3/110> denote identical or different 5- or 6-membered heterocyclic rings which may bear further substituents and/or condensed on benzene rings, or with a derivative of such a compound alkylated on a nitrogen atom and, if desired, the resultant product is reacted with an alkylating agent.  Hydrazone starting materials specified include hydrazones of various benzothiazolones and quinolones.  Many substituted methanes for use as starting materials are listed representative of which are di-[benzo-thiazolyl-(3)] - methane, di - [benzimidazolyl - (2)] - methane, di - [quinolyl - (2)] - methane, di-[pyridyl - (2)] methane, di - [thiazolyl - (2)] methane, di - [benzoxazolyl - (2)] - methane and benzimidazolyl - (2) - 31 - hydroxyquinoxalyl - (21)-methane.  Diazotizable heterocyclic amines specified for use as starting materials include such compounds as amino substituted thiazole, benzthiazole, oxadiazole, pyrazole, triazole, tetrazole, pyridazone and indazole.  The heterocyclic rings may be substituted with such substituents as alkyl, alkoxy, aralkyl, aryl, nitro, acylamino, alkyl sulphonyl, sulphonic acid amide or carboxylic acid amide groups or by halogen.  Alkylating agents specified include dimethyl sulphate, toluene sulphonic acid methyl or chlorethyl ester, methyl iodide, butyl bromide and benzyl chloride. Anions specified include chloride, bromide, iodide, nitrate, perchlorate, sulphate, phosphate, tetrachlorozincate, tetrabromo- and tetrafluorozincate, toluene sulphonate and methyl sulphate ions. The dyes may be used for dyeing or printing cotton, leather, cellulose ester and ether, polyamide, polyurethane and polyester materials and in particular articles of polyacrylonitrile or copolymers containing polyacrylonitrile.  Representative of the many products described in examples are compounds of the formula <FORM:0945820/C3/12>