Patent GB-420593-A (GB)
Title: Production and use of new dyestuffs
IPC: C09B1/514
Filed: 1932-02-17
Abstract: Aminoanthraquinone derivatives; dyeing cellulose esters and ethers.--1,5- or 1,8-dihydroxyanthraquinones containing a further a -arylamino group and an a  - amino or a  - non - aromatically substituted amino group but no other substituents, are prepared from 1,5- or 1,8-dihydroxyanthraquinones substituted by an a -arylamino group or a nitro group or halogen atom or other negative substituent replaceable by amino or substituted amino by the action of ammonia or an amine, by (a) reduction in the case of a nitro group, or (b) reaction with ammonia or a non-aromatic amine, or (c) in the case of a halogen atom by reaction with an acid amide and hydrolysis of the resulting acidylamino compound.  Or these compounds are prepared from 1,5- or 1,8-dihydroxyanthraquinones substituted by an a -amino or a -non-aromatically substituted amino group and in the remaining a -position by an amino group or a nitro group or halogen atom or other negative substituent replaceable by arylamino by the action of an aromatic amine, by replacing the said substituent by the action of a primary aromatic amine. Alternatively, these compounds are prepared from 1,5- or 1,8-dihydroxyanthraquinones substituted in the two remaining a -positions by nitro groups or other negative atoms or groups replaceable by amino or substituted amino by the action of ammonia or an amine, by replacing one of the said negative atoms or groups by an arylamino group by the action of a primary aromatic amine, and the other by an amino group or non-aromatic amino group by (a) reduction in the case of a nitro group, or (b) by the action of ammonia or a non-aromatic amine, (c) in the case of a halogen atom by reaction with an acid amide and hydrolysis of the resulting acidylamino compound.  As replaceable negative substituents in addition to nitro groups and halogen atoms reference is made to sulphonic, hydroxy, alkoxy and aryloxy groups, the a .a <1>-dinitro- and a .a <1>-dihalogen-anthrarufins and -chrysazins being particularly suitable starting materials; for replacing a halogen atom reaction with an arylsulphonamide or phthalimide followed by hydrolysis of the acidyl residue affords a convenient method.  Aryl substituents of the arylamino group are preferably of the benzene series and may contain alkyl, hydroxy, alkoxy, amino, halogen or other substituents, in this connection reference being made to Specifications 402,391, 402,393, 411,877; suitable non - aromatic substituents mentioned are methyl, ethyl, oxyethyl, oxypropyl, #c-chloro-b -oxypropyl, acetyl, cyclohexyl, substituted cyclohexyl, benzyl, hydrogenized benzyl, piperidyl. In examples: (1) 4,8-dinitroanthrarufin is heated with aniline on the water bath and reduced in alkaline glucose solution to give 4 - amino - 8 - phenylamino - 1,5 - dioxyanthraquinone; (2) 4,5-dinitrochrysazin is heated with p-toluidine and reduced as in (1); (3) 4,8-dichloroanthrarufin is condensed with p-toluenesulphonamide, saponified by means of sulphuric acid and condensed with aniline; 4,5-dichloro- or dibromochrysazin may be similarly treated.  The products are used for dyeing cellulose ester and ether materials blue shades, reference being made to cellulose formate, acetate, propionate and butyrate, ethyl and benzyl cellulose, alone or admixed with other textile fibres (including regenerated celluloses).  They are applied to textile materials in solution, aqueous suspension or colloidal dispersion. For convenience, they may be converted into liquid, paste or solid compositions comprising the dye in finely dispersed form and prepared by grinding, by dissolving in a solvent and mixing with water containing or not protective colloids and/or dispersators, or by treating with dispersing agents alone or in the presence of protective colloids and/or liquids.  Specified dispersing agents are sulphoaromatic fatty acid compounds (Specification 242,393, [Class 15 (ii)]), sulphoaromatic ricinoleic acid compounds (Specification 273,819, [Class 15 (ii)]), naphthenic acids or other carbocyclic compounds containing salt-forming groups or salts of such acids or compounds (Specification 224,925, [Class 15 (ii)]), 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-, aralkyl - naphthalene sulphonic acids, sulphite cellulose waste liquors, sulphonic acid compounds of mineral oils, tar oils, brown coal tar oils, and their condensation products with alcohols, sulphonic acid 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).  A further example illustrates the dyeing of cellulose acetate with a dispersion of the product of example 1 in turkey red oil and soap solution. Specification 402,392 also is referred to.