Patent GB-402393-A (GB)
Title: Colouration of cellulose ester and ether materials
IPC: C09B1/32
Filed: 1932-02-17
Abstract: Cellulose esters and ethers, dyeing.--Filaments of cellulose esters or ethers are coloured by applying aqueous suspensions or dispersions of unsulphonated arylaminoanthraquinone compounds having an ether group as a substituent in o-position in the arylamino residue.  The arylamino residue may be of the benzene, naphthalene or other series, and the ether substituent may be a phenyl-, substituted phenyl- or other aryl-ether,--but preferably is a residue of low mass, such as methoxy, ethoxy, o -hydroxyethoxy.  Other substituents such as nitro-, halogen- or alkylgroups may be present in the aryl residue and also in the anthraquinone nucleus; particularly va uable dyes are those containing the o-ether substituted arylamino residue in an a -position and an amino or aliphatically substituted amino or a hydroxy group in para position thereto.  Specific compounds suitable are 1-amino-4-o-methoxyphenylaminoanthraquinone, 1-o -oxyethylamino - 4 - o - methoxyphenylaminoanthraquinone, 1.5-diamino-4.8-di-o-methoxyphenylaminoanthraquinone, 1.8-dihydroxy-4-o-methoxyphenylaminoanthraquinone, and 1-amino-4-o-phenoxyphenylaminoanthraquinone.  For the production of these compounds reactive groups such as nitro, hydroxy, amino, halogen or sulpho groups present as substituents in anthraquinone compounds may be replaced by arylamino residues by the action of appropriately substituted arylamines such as o-anisidine, o-phenetidine or o-aminodiphenylether.  Or aminoanthraquinones may be suitably arylated.  Suitable starting materials are 1-amino-4-hydroxy-, 4-alkoxy-, 4-nitro-, or 4-bromoanthraquinones, quinizarin, 1.5- or 1.8-dinitroanthraquinones, 1.5- or 1.8-dichloranthraquinones or their 4-amino derivatives, 4-nitro- and 4-chlorchrysazin, and 5.8-dichloro-1.2-benzanthraquinone. Alternative syntheses comprise the introduction of an o-ether residue into the arylamino group of an arylaminoanthraquinone, for example by etherifying an o-hydroxy group, or replacing an o-halogen atom by the action of sodium alcoholate.  In addition to the above replacements other reactive groups may be replaced by desired substituents such as amino or alkylamino.  For convenience the dyes are converted into preparations in which they are present in colloidal or dispersed form by grinding (for example, in colloid mills), or 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 the presence of protective colloids. Dispersing agents or protective colloids mentioned are sulphoaromatic fatty acid compounds (Specification 242,393, [Class 15 (ii), Dyeing, Processes &c. for]), sulphoaromatic ricinoleic acid compounds (Specification 273,819, [Class 15 (ii), Dyeing, Processes &c. for]), naphthenic acids or other carbocyclic compounds containing salt-forming groups or salts thereof (Specification 224,925, [Class 15 (ii), Dyeing, Processes &c. for],) sulphonated oil compounds, sulphuric esters of higher aliphatic alcohols, furfuralnaphthalene sulphonic acid compounds (Specification 322,737, [Class 2 (iii), Dyes &c.]), resino-naphthalene sulphonic acid compounds (Specification 323,788, [Class 2 (iii), Dyes &c.]), formaldehyde-naphthalene sulphonic acid compounds, alkyl-, cycloalkyl-, and aralkyl-naphthalene sulphonic acids, sulphite cellulose waste liquors, sulpho compounds of mineral oils, tar oils &c., and their condensation products with alcohols, sulpho compounds of distillation residues of benzaldehyde, carbohydrates (including gums), glue and gelatine and those described in Specifications 219,349, 273,820, [both in Class 15 (ii), Dyeing, Processes &c. for], and 365,170.  Such preparations are used for application to the materials which may be admixed with other textile fibres, by dyeing, printing, stencilling or other method of local application, or they may be used for the colouration of stannous chloride discharges according to Specification 351,457.  In an example cellulose acetate is dyed blue shades from a soap solution containing 1-amino-4-(2<1>-methoxyphenylamino-) -anthraquinone and Turkey Red oil; for printing purposes the dye paste is diluted, and thickened with a gum thickening paste which may also contain a swelling agent (methylated spirits).