Patent GB-782322-A (GB)
Title: Halogenated salicylanilides and compositions containing the same
IPC: C07C233/12
Filed: 1955-09-12
Abstract: An antiseptic detergent soap composition comprises a detergent soap and 0.1-10 per cent by weight, based on the weight of the soap, of a halogenated salicylanilide of the formula <FORM:0782322/III/1> wherein X1 is a chlorine or bromine atom, Y is a methyl or phenyl group and R1 is a halogenated aromatic hydrocarbon group containing one or more benzene nuclei and not more than 3 chlorine and/or bromine atoms, the orthopositions being free from halogen atoms when Y is a methyl group.  Colours, water softeners, antioxidants, perfumes and emmolients may be added to the composition.ALSO:The invention comprises halogenated salicylanilides of the formula <FORM:0782322/IV (a)/1> wherein X is a halogen atom, Y is a methyl or phenyl group and R is a mono- or poly-halogenated aromatic hydrocarbon group containing one or more benzene nuclei, and their preparation by heating a compound of the formula <FORM:0782322/IV (a)/2> wherein -OZ is the residue of a phenol ZOH, with an amine RNH2, in an inert organic solvent.  Values of R include phenyl, tolyl, ethylphenyl, cumenyl, tert.-butylphenyl, iso-amylphenyl, hexylphenyl, xylyl, cymyl and diphenylyl.  The reaction is preferably carried out under reflux using a solvent which acts as an entraining agent for the phenol ZOH liberated, e.g. trichlorbenzene, diphenyl, diphenyl ether, phenylcyclohexane and dicyclohexyl.  In examples: (1) 3-methylsalicylic acid is chlorinated in acetic acid giving 5-chloro-3-methylsalicylic acid, this is heated with phenol and POCl3 in dioxan to give phenyl 5-chloro-3-methylsalicylate and this is condensed with p-chloroaniline in 1,2,4-trichlorobenzene, giving 41,5-dichloro-3-methylsalicylanilide; (2)-(6) 31,5-dichloro-, 21,5-dichloro-, 21,41,5-trichloro- and 31,41,51,5-tetrachloro-3-methyl-salicylanilides and 31,5-dichloro - 21,3 - dimethyl - salicylanilide are prepared similarly; (7) 3-phenylsalicylic acid is chlorinated in acetic acid to give 5-chloro-3-phenylsalicylic acid, this is heated with phenol and POCl3 in dioxan, giving phenyl 5-chloro-3-phenylsalicylate and this condensed with p-chloroaniline in 1,2,4-trichlorobenzene, giving 41,5-dichloro-3-phenylsalicylanilide; (8) 31,5-dichloro-, 21,41,5 - trichloro-, 31,41,5 - trichloro-and 31,41,51,5 - tetrachloro - 3 - phenylsalicyl anilides are prepared similarly. A list of further compounds according to the invention, including bromine-containing and bromine- and chlorine-containing phenyl- and methyl-salicylanilides, is also given.ALSO:An antiseptic detergent soap composition comprises a detergent soap and from 0.1 to 10 per cent, by weight, based on the weight of the soap, of a halogenated salicylanilide of the formula <FORM:0782322/VI/1> wherein X1 is a chlorine or bromine atom, Y is a methyl or phenyl group and R1 is a halogenated aromatic hydrocarbon group containing one or more benzene nuclei and not more than 3 chlorine and/or bromine atoms, the ortho positions being free from halogen atoms when Y is a methyl group. Colours, antioxidants, perfumes, water softeners and emollients may be added to the composition.  The term "detergent soap" is defined as a cleansing composition prepared from an alkaline reacting alkali metal compound such as potassium or sodium hydroxide and a saturated or unsaturated fat, fatty oil or fatty acid.  "Ivory" (Registered Trade Mark) brand neutral, high grade, white tallow soaps containing halogenated salicylanilides according to the invention are referred to.