Patent GB-811113-A (GB)
Title: New metal salts of monoazo compounds
IPC: C09B63/00
Filed: 1955-06-29
Abstract: The invention comprises metal salts of monoazo compounds of formula <FORM:0811113/IV (b)/1> wherein M is a divalent metal, X and Y are -CN, -COCH3, -CONH2 or -COO (alkyl up to 4 carbon atoms) groups and can be the same or different, and the benzene nucleus may also be substituted by -Cl, -Br, -CN, -CF3, -SO2 alkyl, -COO alkyl, -COC6H5, -COOM 1/2 , SO3M 1/2 , -CONRR1 or -SO2NRR1 substituents, wherein R and R1 are hydrogen or alkyl, cycloalkyl, aryl or aralkyl groups, and by an alkyl group of not more than 4 carbon atoms when at least one of the substituents specified above is present.  The compounds are prepared by diazotizing an aminobenzene carboxylic acid which may be suitably substituted, coupling the diazo compound with a coupling component of formula X.CH2.Y and converting the monoazo compound to the metal salt.  The compounds absorb ultra-violet light. Specified aminobenzene carboxylic acids are the aminobenzoic acids, 4-chloro-2-aminobenzoic acid and isomers thereof, 3 - amino - 4 - carboxybenzenesulphonamide and aminoterephthalic acid.  Specified coupling components are acetylacetone, acetoacetamide, malonitrile and alkyl esters of malonic, acetoacetic and cyanoacetic acids. Specified divalent metals are calcium, strontium, barium, manganese, zinc, lead, tin, cadmium and copper.  In examples: (1) anthranilic acid is diazotized and coupled with diethyl malonate, the product is dissolved in aqueous ammonia and barium chloride is added to precipitate the barium salt; (2) as in (1) but coupling 4-chloroanthranilic acid with ethyl cyanoacetate.  The products of both examples are pale yellow powders.ALSO:The invention comprises metal salts of monoazo compounds of formula: <FORM:0811113/IV (c)/1> wherein M is a divalent metal, X and Y are -CN, -COCH3, -CONH2 or -COO(alkyl up to 4 carbon atoms) groups and can be the same or different, and the benzene nucleus may also be substituted by -Cl, -Br, -CN, -CF3, -SO2 Alkyl, -COO Alkyl, -COC6H5, -COOM 1/2 , -SO3M 1/2 , -CONRR1, SO2NRR1 substituents, wherein R and R1 are hydrogen or alkyl, cycloalkyl, aryl or aralkyl groups, and by an alkyl group of not more than 4 carbon atoms when at least one of the substituents specified above is present.  The compounds are prepared by diazotizing an aminobenzene carboxylic acid which may be suitably substituted, coupling the diazo compound with a coupling component of formula X.CH2.Y and converting the monoazo compounds to the metal salt.  The compounds absorb ultraviolet light. Specified aminobenzene carboxylic acids are the aminobenzoic acids, 4-chloro-2-aminobenzoic acid and isomers thereof, 3-amino - 4 - carboxy - benzenesulphonamide and aminoterephthalic acid. Specified coupling components are acetylacetone, acetoacetamide, malonitrile and alkyl esters of malonic, acetoacetic and cyanoacetic acids.  Specified divalent metals are calcium, strontium, barium, manganese, zinc, lead, tin, cadmium and copper.  In examples: (1) anthranilic acid is diazotized and coupled with diethyl malonate, the product is dissolved in aqueous ammonia and barium chloride is added to precipitate the barium salt; (2) as in (1) but coupling 4-chloroanthranilic acid with ethyl cyanoacetate.  The products of both examples are pale yellow powders.