Patent GB-711232-A (GB)
Title: Improvements in or relating to disazo dyestuffs
Inventor: KELLER ERNST
IPC: C09B31/02
Filed: 1951-08-16
Abstract: The invention comprises blue-green dyestuffs of formula:-<FORM:0711232/IV(c)/1> where A is the residue of a diazotized amino-phenyl-benzyl ether or of an amino-diphenyl-ether containing no water-solubilizing acid groups, R is an alkyl group of up to 4 carbon atoms or a carboxymethyl group, X is a hydroxyl, amino, alkylamino, arylamino or acylamino group, one of Y and Y1 is H and the other SO3H, and n is 1 or 2.  They are made by coupling in weak aqueous acid a diazotized amino-phenyl-benzyl or amino-diphenyl ether with a 1-amino-2-lower-alkoxy-(or 2-carboxy-methoxy)-naphthalene-6 or -7 sulphonic acid diazotizing the resultant mono-azo dyestuff and coupling in an alkaline medium with a 1, 8-dihydroxy or 1-amino- (or substituted amino)-8-hydroxy-naphthalene-mono- or di-sulphonic acid. Specified substituents for the benzene rings of the diazo components include methyl and tertiary-amyl groups and halogens especially chlorine. Preferred are amino-benzene compounds containing more than one phenoxy group e.g. those obtained by condensing 1, 3-dichloro-4-nitrobenzene derivatives with the alkali salts of phenol, its homologues or halogen derivatives, with subsequent reduction of the nitro group.  Representative of specified end components are 1, 8-dihydroxy-naphthalene-5 or 6-sulphonic acids, 1, 8-dihydroxy-naphthalene-3, 6-disulphonic acid, 1-amino-8-hydroxy-naphthalene-2, 4-disulphonic acid and the N-alkyl, -aryl and acyl derivatives thereof, the last two specified and acyl derivatives of 1-amino-8-hydroxy-3, 6- disulphonic acid being especially useful.  In examples, the following dyestuffs are made: (1) 1-amino-2, 4-di-(2\sv methylphenoxy)-benzene --> 1-amino-2-methoxynaphthalene-6-sulphonic acid --> 1, 8-dihydroxy-naphthalene-3, 6-disulphonic acid, (2) the aminoazo dyestuff of (1) is coupled with 1-amino-8-hydroxy-naphthalene-2, 4-disulphonic acid, 1-acetylamino-8-hydroxynaphthalene-3, 6-disulphonic acid, 1-(p-toluenesulphonyl)-amino-8-hydroxy-naphthalene-3, 6-disulphonic acid, 1-methylamino-8-hydroxy-naphthalene-4-sulphonic acid or 1-acetylamino-8-hydroxy-naphthalene-4-sulphonic acid, (3) 1-amino-2, 4-di-phenoxybenzene or 1-amino-2, 4-di-(2\sv-methylphenoxy)-benzene--> 1-amino-2-naphthoxy acetic acid-6-sulphonic acid--> 1-amino-8-hydroxy-naphthalene-3, 6-disulphonic acid, (4) 2-amino-4\sv-tert, amyl diphenyl ether--> 1-amino-2-methoxynaphthalene-6-sulphonic acid --> 1-(p-toluenesulphonyl)-amino-8-hydroxy-naphthalene-3, 6-disulphonic acid, or 1-amino-8-hydroxy-naphthalene-3, 6-disulphonic acid, may be the end component or the initial diazo component may be 2-amino-4\sv-octyldiphenyl ether, (5) 4-chloro-2-amino-diphenyl ether--> 1-amino-2-methoxynaphthalene-6-sulphonic acid --> 1-(p-toluenephenyl)-amino-8-hydroxy-naphthalene-3, 6-disulphonic acid, 1-benzenesulphonyl-amino-8-hydroxy-naphthalene-3, 6-disulphonic acid or 1-amino-8-hydroxynaphthalene-2, 4-disulphonic acid, (6) 2-amino-4-methylphenyl benzyl ether--> 1-amino-2-methoxynaphthalene-6-sulphonic acid --> 1-amino-8-hydroxynaphthalene-2, 4-disulphonic acid, the starting and end components may be 2-amino-4-amyl-benzyl ether and 1-amino-8-hydroxynaphthalene-3, 6-disulphonic acid respectively and in (7) 1-aminophenyl- 2, 5-dibenzyl ether or 1-aminophenyl-2, 4-dibenzyl ether --> 1-amino-2-methoxynaphthalene-6-sulphonic acid --> 1-amino-8-hydroxynaphthalene-2, 4- disulphonic acid.  The dyestuffs are used in the silver-dye-bleach photographic process cf. Specification 711,233, [Group XX].