Patent GB-420591-A (GB)
Title: Production and use of new dyestuffs
IPC: C09B1/514
Filed: 1932-02-17
Abstract: Aminoanthraquinones; dyeing cellulose ester and ether materials.--Anthraquinone derivatives containing an a -arylamino of the benzene series group, an a -amino or a -non-aromatically substituted amino group, and an a -hydroxy group together with a further amino group or non-aromatically substituted amino group or hydroxy group, or together with further substituents at least one of which is a hydroxy group or an amino group or a non-aromatically substituted amino group, are prepared from anthraquinone derivatives having the required substituents except that in place of the arylamino group or at least one amino or non-aromatically substituted amino group there is present an amino group or a nitro group or a halogen atom or other negative substituent replaceable by amino or substituted amino by the action of ammonia or an amine, by (a) when the arylamino group is already present by replacing the replaceable substituent or substituents by amino or non-aromatically substituted amino by the action of ammonia or a non-aromatic amine, or in the case of a nitro group or groups by reduction, or in the case of halogen by reaction with an acid amide and hydrolysis of the resulting acidylamino compound, or (b) when the amino or non-aromatically substituted amino group or groups are already present, by the action of a primary aromatic amine of the benzene series.  The foregoing compounds containing a non-aromatically substituted amino group are also prepared by treating those of the foregoing products which contain a primary amino group with acylating, aralkylating or alkylating agents (including substituted alkylating agents).  Particular mention is made of the compounds containing besides the three specified a -substituents a further a -hydroxy group.  Replaceable negative substituents in addition to nitro groups and halogen atoms are sulphonic, hydroxy, alkoxy, and aryloxy groups, specified starting materials being 4,8-diaminoanthrarufin, 1 - amino - 4,5,8 - trioxyanthraquinone and 1,4-diamino - 5,6 - dioxyanthraquinone.  Replacement of hydroxy groups by amino or hydroxy and amino groups by substituted amino groups is advantageously effected by treating the leuco anthraquinone derivative (cf. Specification 310,784, [Class 2 (iii)]).  The phenyl group of the phenylamino substituent may be substituted for example by alkyl, hydroxy, alkoxy, amino, halogen, in this connection reference being made to Specifications 402,391, 402,393, 411,877, and 416,612.  Suitable substituents in the non-aromatically substituted amino groups are methyl, ethyl, oxyethyl, oxypropyl, #c-chloro-b -oxypropyl, acetyl, cyclohexyl, substituted cyclohexyl, benzyl, piperidyl.  In examples: (1) 1,4,5 - trioxy - 8 - aminoanthraquinone is condensed with o-anisidine in presence of boric acid; (2) o-anisidine is replaced in (1) by aniline; (3) 1,4-diamino-5,6-dioxyanthraquinone is condensed with aniline in presence of acetic acid and sodium acetate; (4) 1 - amino - 4 - phenylamino - 5,8 - dioxy - anthraquinone is condensed with ethylenechlorhydrin.  The products are used for colouring cellulose ester and either materials blue shades, cellulose formate, acetate, propionate, and butyrate and ethyl and benzyl cellulose being mentioned; such fibres may be dyed admixed with other textile fibres (including regenerated celluloses).  The products are applied in solution, aqueous suspension or colloidal dispersion.  For convenience they may be converted into liquid, paste or solid compositions in which the dyes are present in finely divided condition, and which are 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.  Dispersing agents specified 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)]), resinonaphthalene sulphonic acid compounds (Specification 323,788, [Class 2 (iii)]), formaldehydenaphthalene sulphonic acid compounds, alkyl-, cycloalkyl- and 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.  The products are applied to the materials by dyeing, printing, stencilling &c., or they may be employed for colouring stannous chloride discharges (cf. Specification 351,457).  In an example, the product of (2) above is used in turkey red oil dispersion for dyeing cellulose acetate blue shades.  The production and use in dyeing cellulose ester and ether materials of 1,5- or 1,8-dioxyanthraquinones containing an a -arylamino group and an a -amino or a -non-aromatically substituted amino group is disclaimed (Specification 420,593). Specifications 219,349, 273,820, [both in Class 15 (ii)], 343,444, 365,170, 402,392, and 416,611 also are referred to.