Patent GB-411877-A (GB)
Title: Manufacture and application of new dyestuffs
IPC: C09B1/514
Filed: 1932-02-17
Abstract: Amini-anthraquinone derivatives; dyeing cellulose esters and ethers. Unsulphonated anthraquinone compounds having as substituents an acidylaminoarylamino group and a hydroxyl group, are prepared by the action of a primary arylamine substituted in the nucleus by an acidylamino group upon a hydroxy anthraquinone containing a further negative atom or group or an amino group, which substituent is replaceable by arylamino by the action of an aromatic amine. Reference is made to the replacement of nitro, hydroxy, methoxy, amino, halogeno and sulpho groups by acidylaminoarylamino groups of which p-aminoacetanilide monacetyl - p - phenylenediamine and monacetyl - p - toluylenediamine are specified; suitable starting materials are 1 - amino - 4 - oxyanthraquinone, 1 - oxy - 4 - chlor - or bromanthraquinone, 1 - oxy - 4 - nitroanthraquinone, 4 - nitrochrysazin 4-chlorchrysazin, 4.8 - dinitro - or 4.8 - diaminoanthrarufin, quinizarin.  Replacement of hydroxy groups by substituted amino groups is frequently effected advantageously by using the anthraquinone in the form of a leuco derivative (c.f. Specification 310,784, [Class 2 (iii)]).  Alternatively the desired anthraquinone compounds are prepared by acidylating a primary or secondary amino group present as a substituent in an arylamino group of a hydroxyarylaminoanthraquinone.  In examples (1) 1 - oxy - 4 - chloranthraquinone is condensed with p-phenylenediamine and the product acetylated: (2) p-chlorchrysazin is treated as in (1) : (3) 1 - oxy - 4 - nitroanthraquinone is condensed with monacetyl-p-phenylenediamine: (4) leuco-quinizarin is condensed with monoacetyl-p-phenylenediamine.  Reference is made to compounds wherein the acidyl residue is formyl, propionyl, benzoyl, etc., and wherein the aryl residues contain further halogen, nitro, alkoxy, alkyl substituents in addition to acidylamino.  The products are used for dyeing cellulose ester and ether materials, reference being made to cellulose formate, propionate and butyrate, ethyl and benzyl cellulose, alone or admixed with other textile fibres.  The products are applied to textile materials in solution, aqueous suspension or after colloidal dispersion.  For convenience they may be converted into liquid, paste, or powdered compositions comprising the dye in finely divided form and prepared, for example, by grinding, by dissolving in a solvent and mixing with water containing or not protective colloids and/or dispersators, or by treatment with dispersing agents alone or in presence of protective colloids and/or liquids.  Specified dispersing agents are sulphoaromatic fatty acid compounds (Specification 242,393, [Class 2 (iii)], sulphoaromatic ricinoleic acid compounds (Specification 273,819, [Class 2 (iii)]), naphthenic acids or other carbocyclic compounds containing salt-forming groups or salts of such acids or compounds (Specification 224,925, [Class 2 (iii)]), sulphonated oil compounds, sulphuric esters of higher aliphatic alcohols, furfural naphthalene sulphonic acid compounds (Specification 322,737, [Class 2 (iii)]), resino-naphthalene sulphonic acid compounds (Specification 323,788, [Class 2 (iii)]), formaldehyde-naphthalene sulphonic acid compounds, alkyl-,cycloalkyl-, and aralkylnaphthalene sulphonic acids, sulphite cellulose waste liquors, sulphonic acid compounds of mineral oils, tar oils, brown coal tar oils, and condensation products of these with alcohols, sulpho compounds of distillation residues of benzaldehyde, carbohydrates including gums, glue and gelatine.  They may be applied to the materials by dyeing, printing, stencilling, &c., or they may be used for colouring stannous chloride discharges (Specification 351,457).  An example illustrates the dyeing of a cellulose acetate fabric in blue-violet shades by 1-oxy-4 - (p-acetylaminophenylamino) - anthraquinone boiled in pyridine and diluted with soap solution prior to filtering into the dyebath. Specifications 219,349, 273,820, [both in Class 2 (iii)], 365,170, 402,391, and 402,393, are referred to.