Patent GB-402391-A (GB)
Title: Colouration of cellulose ester and ether materials
IPC: C09B1/32
Filed: 1932-02-17
Abstract: Cellulose esters or ethers, dyeing.--Cellulose esters or ethers are coloured with an anthraquinone compound having as a substituent in the nucleus a m-alkylphenylamino or a m-alkoxy-phenylamino group, preferably sulpho groups being absent. Valuable colouring matters are those in which the m-alkylphenylamino- or m-alkoxyphenylamino groups are in a -positions and have hydroxy, amino or aliphatically substituted amino groups in the para position; specific dyestuffs mentioned are 1-oxy-4-m-tolylaminoanthraquinone, 1 - amino - 4 - m - tolylaminoanthranquinone, 1 - methylamino-4-m - tolylaminoanthraquinone, 1 . 5 - diamino - 4 . 8 - di - m - tolylaminoanthraquinone, 1 . 8 - dihydroxy - 4 - m - tolylaminoanthraquinone, 1 - amino - 4 - (5<1> - methyl - 2<1> -methoxyphenylamino) - anthraquinone, 1 - amino - 4 - (3<1> - methyl - 4<1> - acetylaminophenylamino) - anthraquinone, 1 - amino - 4 - (2<1> . 5<1> - dimethylphenylamino) - anthraquinone, and 1 - amino - 4 - (3<1> . 5<1> - dimethylphenylamino) - anthraquinone. Othe substituents such as halogen or nitro groups may be present in the phenyl residue, and the anthraquinone nucleus may bear other substituents such as arylamino residues containing an o-alkoxy group (cf. Specification 402,393), or an acidylamino group.  For the production of these compounds reactive groups such as nitro, hydroxy, amino, halogen or sulpho groups present as substituents in anthraquinone derivatives may be replaced by phenylamino residues by the action of appropriately substituted anilines, for example m-anisidine, m-toluidine, p-xylidine, sym-xylidine, 3-amino-4-methoxytoluene, and monacetyl-p-toluylene-diamine; or aminoanthraquinones may be arylated in the desired manner.  In addition other reactive groups present may be converted into other substituents before or after the introduction of the m-substituted phenylamino residue; thus a nitro group may be reduced to or replaced by an amino group or a nitro or hydroxy group or halogen atom replaced by an amino or aliphatically substituted amino group such as methylamine or oxyethylamine; when amidation of hydroxy groups is concerned reaction may be facilitated by first reducing the anthraquinone compound (cf. Specification 310,784, [Class 2 (ii), Cellulose &c.]); or halogen atoms may be replaced by alkoxy groups by the action of sodium alcoholates, or hydroxy groups may be esterified. Examples of suitable starting materials are 1-amino-4-hydroxy-, or alkoxy-, or bromo-, or nitro-anthraquinones, 1-hydroxy-4-bromo- or chloro-anthraquinones, 1.5- or 1.8-dinitroanthraquinones, 1.5- or 1.8-dichloroanthraquinones or their 4-amino derivatives, quinzarin, 4-chloro-, 4-nitro-, and dinitrochrysazins, dinitroanthrarufin, 1 . 5 - dinitro - 4 . 8 - diaminoanthraquinone, 1 . 8 - dinitro - 4.5-diaminoanthraquinone and 5.8-dichloro-1.2-benzanthraquinone.  The dyestuffs are applied to the material which may be admixed with other textile fibres, in solution, or in aqueous suspension, or after being brought into colloidal form. For convenience they may be converted into preparations in which the colouring matter is 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 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 (iii), Dyeing, Processss &c. for]), naphthenic acids or other carbocyclic compounds containing salt-forming groups or salts thereof (Specification 244,925, [Class 15 (iii), Dyeing, Processes &c. for]), sulphonated oil compounds, sulphuric esters of higher aliphatic alcohols, furfuralnaphthalene sulphuric acid compounds (Specification 322,737, [Class 2 (iii), Dyes &c.]), resinonaphthalene sulphonic acid compounds (Specification 323,788, [Class 2 (iii), Dyes &c.],) formaldehyde-naphthalene sulphonic acid compounds, alkyl-, cycloalkyl- and aralkylnaphthalene sulphonic acids, sulphite cellulose waste liquors, sulpho compounds of mineral oils, tar oils &c., and their condensation products with alcohols, sulpho derivatives of distillation residues of benzaldehyde, carbohydrates (including gums), glue and gelatine.  Such preparations may be used for application to the materials 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 1-amino-4-m-tolylaminoanthraquinone (from 1-amino-4-methoxyanthraquinone and m-toluidine) is dispersed in soap solution, and cellulose acetate dyed a bright blue shade from such solution; the goods may be printed with the dyestuff paste suitably diluted and thickened with a gum thickening paste which may contain swelling agents (methylated spirits) The Provisional Specifications relates to the use of m-alkylarylamino or m-alkoxyarylamino-anthraquinones for dyeing cellulose ester and ether materials.  Specification 224,925, [Class 15 (ii), Dyeing, Processes &c. for], also is referred to.