Patent GB-879170-A (GB)
Title: Improvements relating to dioxazine dyestuffs and their use
IPC: C09B19/02
Filed: 1958-05-09
Abstract: Viscose and acetyl cellulose is dyed in the mass, polyvinyl chloride compositions are coloured and urea-alkyd resin lacquers are pigmented by dyestuffs of the formula:-  <FORM:0879170/IV (a)/1> where R1 and R2 each represent a substituted or unsubstituted phenyl radical or the residue of a primary or secondary amine linked through the nitrogen atom and wherein the rings A may be further substituted by halogen, alkyl, alkoxy, aralkoxy or sulphonic acid groups.  In Examples (7), a lacquer contains a pigment of the above formula, titanium dioxide, a 60% solution of a modified urea-alkyd resin in xylene/butanol 1 : 1, turpentine and xylene; and (8) a composition contains polyvinyl chloride a pigment of the above formula, dioctyl phthalate and titanium dioxide.ALSO:N-Triazinyl-p-phenylene diamines of the formula:-  <FORM:0879170/IV (b)/1> where R1 and R2 are phenyl, piperazino, piperidino, morpholino, n-butylamino, di-n-butylamino, hexadecylamino, octadecylamino, benzylamino, phenylamino, 2-, 3- or 4-methylphenylamino, 2 : 4 -dimethylphenylamino, 2-, 3- or 4-chlorophenylamino, 2 : 4-, 2 : 5- or 3 : 4-dichlorophenylamino, 2- or 4-methoxyphenylamino, 2:4-dimethoxyphenylamino, N-ethyl-phenylamino or a - or b -naphthylamino, X is hydrogen, methoxy, ethoxy or benzyloxy and the ring A may contain as a further substituent in the para position to X a methoxy, ethoxy, benzyloxy, methyl, chloro or sulphonic acid group, are made by saponification of the corresponding compound in which the primary amino group is acylated.  4-(41 : 61- Dimorpholino- 11 : 31 : 51-triazinyl-(21)-amino)-acetanilide or the corresponding compound containing methoxy groups in the 2- and 5-positions is made by reacting with morpholine 4-(41 : 61-dichlorotriazinyl- (21)-amino)-acetanilide or 4-(41 : 61-dichlorotriazinyl-(21)-amino)-2 : 5-dimethoxyacetanilide respectively, which compounds are obtained by reacting 4-amino-acetanilide or 4-amino-2 : 5-dimethoxy-acetanilide with cyanuric chloride.  4[41 : 61-di(o-, m or p-chlorophenylamino)- 11 : 31 : 51-triazinyl- (21)-amino]-2 : 5-di-methoxy-acetanilide is made by reacting o-, m- or p-chloroaniline with 4-(41 : 61-dichloro-11 : 31 : 51-triazinyl-(21)-amino)- 2 : 5-dimethoxy-acetanilide. 4-[41(o-chlorophenylamino)- 61-(p-methoxy-phenylamino) -11 : 31 : 51- triazinylamino] -2 : 5-dimethoxy-acetanilide is made by reacting 4-(41 : 61- dichloro- 11 : 31 : 51- triazinylamino)-2 : 5-diimethoxy-acetanilide with o-chloroaniline and then with p-methoxyaniline.  4-(41 : 61 - diphenylamino- 11 : 31 : 51-triazinylamino)-3-sulpho-acetanilide is made by reacting aniline with 4-(41 : 61-dichloro-11 : 31 : 51-triazinylamino)-3-sulpho-acetanilide.ALSO:The invention comprises dioxazine dyestuffs of the formula:-  <FORM:0879170/IV(c)/1> where R1 and R2 each represent a substituted or unsubstituted phenyl radical or the residue of a primary or secondary amine linked through the nitrogen atom and wherein the rings A may be further substituted by halogen, alkyl, alkoxy, aralkoxy or sulphonic acid groups.  The dyestuffs are made by condensing with chloranil a compound of the formula:-  <FORM:0879170/IV(c)/2> where R1, R2 and A have the meanings above and X is hydrogen or an ether group and simultaneously or subsequently converting the condensation products by known methods into dioxazine dyestuffs of the above formula.  The dyestuffs may be subsequently sulphonated or further sulphonated.  The dyestuffs are converted into a finely-divided form by precipitation from organic or inorganic acids or by milling in the presence of inorganic or organic salts.  They may be used for shading phthalocyanine pigments, for printing textiles, for dyeing cellulose material such as paper, for mass-dyeing viscose or acetyl cellulose and for pigmenting polyvinyl chloride compositions, lacquers, paints and printing inks, giving violet-blue, violet and blueish-red shades.