Patent GB-457458-A (GB)
Title: Manufacture of azo-dyestuffs
IPC: B62J7/00
Filed: 1935-05-27
Abstract: Monoazo dyestuffs insoluble in water but soluble in organic solvents are manufactured by diazotizing a mixture of aniline derivatives containing in the nucleus an aliphatic residue of the constitution <FORM:0457458/IV/1> where R is an aliphatic radicle containing at least two carbon atoms, and coupling with a coupling component, neither component containing groups lending solubility in water or nitro-groups. Dis-azo dyestuffs are manufactured by employing in the foregoing process a coupling component containing a diazotizable amino-group, e.g. m-toluidine, p-xylidine, 1-methyl-2- or 3-amino-4-methoxybenzene, 2-amino-1 : 4-dialkoxybenzenes and 1-amino-2-alkoxynaphthalenes, diazotizing, and coupling with a coupling component not containing groups lending solubility in water or nitrogroups, e.g. p-cresol, cyclohexylphenol, m-phenylenediamine, naphthols and their nuclear substitution products, b  - alkylaminonaphthalenes, and amides of the oxynaphthoic acids substituted at the nitrogen by hydrocarbon residues, especially alkyl radicles.  Examples describe the manufacture of the following dyestuffs: (1) a mixture of o-, p-and m-amino-sec. butylbenzenes --> 2 : 3-oxynaphthoic acid anilide; the product yields red solutions in organic solvents; (2) an aminobutylbenzene mixture --> 2 : 3-oxynaphthoic acid anilide; the product colours organic media red; (3) an aminobutylbenzene mixture --> 1-phenyl-3-methyl-5-pyrazolone; the product yields yellow solutions in organic solvents; (4) an aminobutylbenzene mixture --> 2 : 4-dioxyquinoline; the product yields yellow solutions in organic solvents; (5) an aminoamylbenzene mixture --> 2 : 3-oxynaphthoic acid anilide; the product yields red solutions; (6) an aminobutylbenzene mixture --> m-toluidine --> b -naphthol; the product yields bluish-red solutions; by replacing the b -naphthol by 2 : 3-oxynaphthoic acid isohexylamide (obtainable from 2 : 3-oxynaphthoic acid and commercial isohexylamine), a dyestuff of a bluer tint is obtained; (7) an aminobutylbenzene mixture --> p-xylidine --> b -naphthol; the product yields blue-red solutions; (8) an aminoamylbenzene mixture --> 3-amino-4-methoxy-1-methylbenzene --> 2 : 3-oxynaphthoic acid n-butylamide; the product yields violet solutions; (9) an aminobutylbenzene mixture --> aminohydroquinone dimethyl ether --> b -naphthol; the product yields blue-violet solutions; (10) an aminobutylbenzene mixture --> 1-amino-2-naphthol ethyl ether --> 2 : 3-oxynaphthoic acid n-butylamide; the product colours organic media green-blue.  A table gives the solubility in benzene, linseed oil and butyl acetate of the dyestuffs obtained by coupling 2 : 3 oxynaphthoic acid anilide with a mixture of o-, p- and m-amino-sec. butylbenzenes, a mixture of o-, p- and m-amino-sec. and prim.-butylbenzenes, a mixture of o-, p- and m-aminoamylbenzenes and a mixture of aminodecylbenzenes, and for comparison with o-, p- and a mixture of o-, p- and m-aminoethylbenzenes, p-aminoisobutylbenzene, p-amino-prim. butylbenzene, a mixture of o-, m- and p-amino-prim. butylbenzenes and p-amino-sec. butylbenzene.  A second table gives the solubility of the dyestuffs of examples (6) to (9) and also the dyestuffs aminobutylbenzene mixture --> cresidine --> p-cresol, 1 : 4-methylnaphthol or b -ethylaminonaphthalene, aminobutylbenzene mixture --> aminohydroquinone dimethyl ether --> p-cyclohexylphenol and aminoamylbenzene mixture --> cresidine --> b -naphthol, and for comparison the dyestuff p-amino-prim. butylbenzene --> cresidine --> b -naphthol.  Mixtures of amines suitable for use in the above process are obtainable by nitration and reduction from suitable alkyl benzenes or mixtures of alkylbenzenes.  The mixtures employed in the foregoing examples are obtained as follows: (1) benzene is p  reacted with sec. butyl chloride in the presence of aluminium chloride and the product is nitrated and reduced; (2) benzene is reacted with prim. butyl chloride in the presence of aluminium chloride and the product is nitrated and reduced; (5) benzene is condensed with a mixture of amyl chlorides obtained by chlorinating pentane and the product is nitrated and reduced.