Patent GB-1077654-A (GB)
Title: Water-insoluble monoazo dyestuffs and processes for their manufacture
IPC: C09B29/20
Filed: 1964-10-16
Abstract: The invention comprises water-insoluble monoazo dyestuffs of the formula <FORM:1077654/C4-C5/1> wherein X represents H or chlorine atom, a methyl, alkoxy, aryloxy or carboxylic acid ester group, R represents H or a halogen atom or an alkoxy group, Y represents -SO2- or -CO-, "Alk" represents alkylene or alkylidene, Z represents a carboxylic acid amide or sulphonic acid amide group which may contain substituents, and A represents the radical of a coupling component free from SO3H and COOH groups and capable of coupling in a position adjacent to a hydroxyl group.  The dyes may be prepared by the usual coupling processes which may be carried out in a solvent such as glacial acetic acid, acetone, dioxane tetrahydrofuran, formamide, dimethyl formamide or dimethyl sulphoxide or by coupling on fibres (see Division D1).  Preferred coupling components are the arylamides of 2:3-hydroxy-naphthoic acid and acetoacetic acid and derivatives of 5pyrazolone. The physical properties of the product when prepared in aqueous medium may be improved by heating the coupling mixture while adding small amounts of an organic solvent, for example, pyridine, a hydrocarbon, a phthalic acid dialkylester or resin soap.  The dyestuffs may be improved by grinding the crude pigment with an appropriate grinding auxiliary agent in order to convert it into a finely divided form.  Examples are given for the preparation of the dyes.ALSO:Vinyl resins, particularly polyvinyl chloride, are coloured with dyestuffs of the formula <FORM:1077654/C3/1> wherein X represents H, Cl, Ch3, alkoxy, aryloxy or a carboxylic acid ester group, R represents H, halogen or alkoxy, Y represents -SO2- or -CO-, Alk represents an alkylidene or alkylene radical, Z represents a substituted or unsubstituted carboxylic or sulphonic acid amide group, and A represents the radical of a coupling component free from SO3H and COOH groups and capable of coupling in a position adjacent to an OH group.ALSO:Water-insoluble monoazo dyestuffs of the formula:-  <FORM:1077654/D1-D2/1> wherein X represents H or chlorine atom, methyl, alkoxy, aryloxy, or carboxylic acid ester group, R represents H or a halogen atom or an alkoxy group, Y represents -SO2- or -CO-, 'Alk' represents alkylene or alkylidene, Z represents a carboxylic acid amide or sulphonic acid amide group which may contain substituents, and A represents the residue of a coupling component free from SO3H and COOH groups and capable of coupling in a position adjacent to a hydroxyl group, are prepared by coupling on fibres of natural or synthetic origin, for example, cotton, regenerated cellulose, polyvinylalcohol fibres and acetate rayon or polyamide fibres using the ice colour technique for dyeing and printing processes.  Also dyestuffs of the above formula may be applied to textile materials made from vegetable or animal fibres, such as wool, cotton or linen, from semi-synethetic fibres, such as regenerated cellulose, or from synthetic fibres.  The dyestuffs may also be added to spinning solutions, and they may be used to colour natural or synthetic resins.  An example is given where a cotton yarn is impregnated in a bath containing a coupling component, denatured ethanol, formaldehyde and a product obtained by condensation of high M.W. fatty acids and protein decomposition products, and then developed in a bath containing a diazo component and a product obtained by the action of about 20 mols of ethylene oxide on octadecyl alcohol.