ª¤,ª¤-dihydroxymonoazo dyestuffs of the benzene-azo-indandione series and metal complex compounds thereof

• Main Author: ENDERS EDGAR
• Format: Patent
• Language: English
• Published: 25.06.1958
• Subjects: ADHESIVES; CHEMISTRY; DYES; LAKES; METALLURGY; MISCELLANEOUS APPLICATIONS OF MATERIALS; MISCELLANEOUS COMPOSITIONS; MORDANTS; NATURAL RESINS; ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES; PAINTS; POLISHES

The invention comprises monoazo dyes of formula <FORM:0797231/IV (b)/1> wherein X is a sulphonamide or alkyl sulphone radical, Y is hydrogen or a substituent other than a carboxylic or sulphonic acid group, and the metal complexes thereof. The metal-free dyestuffs are prepared by coupling suitable o-amino-phenols with indandione-(1 : 3) or with derivatives thereof which form indandione-(1 : 3) under the coupling conditions, such as indandione-(1 : 3)-2-carboxylic acid. The preferred metal complexes are the chromium and cobalt complexes which are prepared in known manner. The metallized dyestuffs dye wool, silk and polyamide fibres in red to brown shades. In examples cobalt and chromium complexes of the following dyestuffs are prepared: (1) 1-amino-2-phenol-5-sulphodimethylamide or -sulphodiethylamide or -sulpho - methyl - a - or - b - hydroxyethylamide --> indandione-(1 : 3) in the presence of ammonia; (2) indandione-(1 : 3)-2-carboxylic acid is converted into its sodium salt by reaction with a solution of sodium in alcohol, the resulting mixture is diluted with water, a solution of the diazo compound of 1 - amino - 2 - phenol - 5 - sulphomethylamide or -sulphoethylamide or -sulphobutylamide or -sulphoanilide or -sulphonamide is added and coupling takes place in the presence of ammonia; (3) 1-amino-2-phenol-5-methylsulphone or -chloromethylsulphone or -ethylsulphone --> indandione-(1 : 3) as in (1); (4) 1-amino-2-phenol - 4 - sulphodimethylamide --> indandione-(1 : 3) as in (1). The following diazo components are also specified and coupled with indandione - (1 : 3) : 1 - amino - 2 - hydroxy - 5 - chloro- or -methyl-benzene-4-sulphonamide, 1-amino - 2 - phenol - 5 - sulpho - (21 - methyl or -methoxy or -chloro)-anilide, 1-amino-2-phenol-5 - sulpho - (g - hydroxy or -methoxy) - propylamide, 1 - amino - 2 - phenol - 5 - sulpho - (31 - methanesulphonylamino)-anilide and 1-amino-2 - phenol - 4 - sulphoanilide. Specifications 667,168, 736,034, 737,619 and 743,583 are referred to.