Patent GB-908292-A (GB)
Title: Halogenated nitrocarbanilides and compositions containing the same
IPC: C11D3/48
Filed: 1959-03-16
Abstract: A cleansing composition comprises an organic detergent and a halogenated nitrocarbanilide of the formula <FORM:0908292/III/1> wherein R is a chlorine or bromine atom, R1 is an alkyl group of 1-5 carbon atoms, or is H, Cl, or Br, and X is an oxygen or sulphur atom. Compounds of this formula impart bacteriostatic or antiseptic properties to detergent compositions, including cosmetic compositions such as toilet soaps, shaving creams, and shampoos.  The organic detergent may be anionic or non-ionic, e.g. it may be an alkali metal soap of a higher fatty acid such as stearic, lauric, palmitic, oleic, linoleic, or ricinoleic acid, or a soap derived from tallow, lard, coconut oil, palm oil, castor oil, olive oil, hydrogenated fish oil, or cottonseed oil.  Alkali metal salts of organic sulphonates and sulphates may be used, e.g. alkyl aryl sulphonates in which the alkyl group is a straight or branched chain alkyl group of 8-22 carbon atoms and in which the aryl group is derived from benzene, toluene, the xylenes, phenol, the cresols, or naphthalene.  Long chain alkyl sulphonates such as sodium octadecane sulphonate may be used. Sulphate detergents include sodium coconut oil monoglyceride monosulphate, sodium lauryl sulphate and sodium cetyl sulphate. Other detergents specified are the sodium salts of N-oleyl taurine, sulphosuccinic esters, and bisulphates of dialkyl polymethylene dicarboxylates. Non-ionic surface active agents include polyalkylene oxide derivatives of fatty acids such as lauric and stearic acids and mixed acids obtained from fats and oils or by the oxidation of petroleum fractions.  Polyalkylene oxide derivatives of alcohols, phenols, and amines, may be used.  In examples neutral high grade white soap is given good bacteriostatic or antiseptic properties by incorporating small proportions of 3,4-dichloro-, 3-chloro, 3-chloro-4-methyl-, and 3-bromo-31-nitrocarbanilide, and 3-chloro-31-nitro-thiocarbanilide.  An antiseptic shampoo is prepared from triethanolamine lauryl sulphate, methyl cellulose, propylene glycol, potassium stearate, water, and 3,4-dichloro-31-nitrocarbanilide.  A cleansing composition comprises a tall oil ethylene oxide condensation product, sodium dodecyl benzene sulphonate, sodium carboxymethyl cellulose, sodium tripolyphosphate, sodium sulphate, and 3,4-dichloro-31-nitrocarbanilide.ALSO:Compounds of the formula <FORM:0908292/IV (b)/1> in which R is a chlorine or bromine atom, R1 is an alkyl group having up to 5 carbon atoms or a hydrogen, chlorine, or bromine atom, and X is an oxygen or sulphur atom have antiseptic and bacteriostatic properties and are incorporated in cleansing compositions (see Group III).  Those compounds of the above formula in which (a) R is chlorine or bromine, R1 is chlorine, bromine, or 2-5 C alkyl, and X is O or S, or (b) R is bromine, R1 is H and X is O or S, or (c) R is chlorine, R1 is methyl and X is O or S, or (d) R is chlorine, R1 is H and X is sulphur, are claimed as new compounds.  The compounds may be obtained by reacting m-nitrophenylisocyanate or isothiocyanate with an aniline having chlorine or bromine in m-position with respect to the amino group and there may also be present a second chlorine or bromine atom in the p-position or an alkyl group.  They may also be prepared by reacting m-nitroaniline with a phenyl isocyanate or isothiocyanate having chlorine or bromine in m-position and there may also be a second chlorine or bromine atom in p-position or an alkyl group.  The reaction may be carried out in solution e.g. in benzene, acetone, dioxane, hexane, or diethyl ether, with application of heat if desired.  The compounds 3.4-dichloro-, 3-chloro-4-methyl-, and 3-bromo-31-nitrocarbanilide, and 3-chloro-31-nitrothiocarbanilide are specifically claimed. The following compounds are also described or referred to:- 3-chloro-31-nitrocarbanilide, 3.4 - dibromo-, 3 - chloro-4-ethyl-, 3-bromo-4-butyl-, and 3-chloro-4-amyl-31-nitrocarbanilide, and 3.4-dichloro-, 3-chloro-4-butyl-, and 3-bromo-4-methyl-31-nitrothiocarbanilide.