Patent GB-698536-A (GB)
Title: 3-alkyl-2,2-dihydroxy-3, 5,5-trihalodiphenylmethanes
Filed: 1952-02-29
Abstract: The invention comprises compounds of the formula <FORM:0698536/IV (b)/1> in which R represents a propyl or butyl radical and each X represents bromine or chlorine.  They can be obtained by reaction a compound of formula <FORM:0698536/IV (b)/2> with a substituted saligenin of formula <FORM:0698536/IV (b)/3> or by reacting a 3-propyl or 3-butyl-5-halosaligenin with a 2,4-dihalo phenol, the halogen being chlorine or bromine, in the presence of an acid condensing agent, e.g. sulphuric acid, glacial acetic acid saturated with hydrogen chloride or mixed acetic and sulphuric acids.  From 8 to 20 moles. of 70 to 100 per cent sulphuric acid per mole. of saligenin derivative is suitable.  The reactants are reacted first at 20 DEG  to 35 DEG  C. and then at 70 DEG  to 130 DEG  C.  The product may be recovered as its alkali metal salt and regenerated by acidification.  The alkyl radicals may be straight or branched chain. The saligenin derivatives employed can be p  produced by reacting the appropriate 2,4-dihalophenol or 2-alkyl-4-halophenol as a phenolate with formaldehyde, e.g. at 20 DEG  to 90 DEG  C. followed by acidification.  In examples: (1) 3 - n - butyl - 2,21 - dihydroxy, 31,5,51 - trichlorodiphenylmethane is prepared by reacting 2 - n - butyl - 4 - chlorophenol and 3,5 - dichlorosaligenin, the reaction mixture being diluted with chlorobenzene; (2) 3-isopropyl-2,21-dihydroxy-31,5, 51-trichlorodiphenyl methane is prepared from 3,5-dichlorosaligenin (from 2,4-dichlorophenol and formaldehyde) and 4-chloro-2-isopropyl phenol; (3) 2-sec-butyl-4-chlorophenol and 3,5-dichlorosaligenin are reacted to give 3-sec-butyl-2,21-dihydroxy-3,5, 51-trichlorodiphenylmethane; (4) 5-chloro-3-isopropylsaligenin (from 4-chloro-2-isopropylphenol and formaldehyde) and 4-bromo-2-chlorophenol are reacted to give 3-isopropyl-2,21-dihydroxy-51-bromo - 31,5 - dichlorodiphenylmethane; (5) 3-isopropyl - 2,21 - dihydroxy - 5 - chloro - 31,51\h - dibromo-diphenylmethane is prepared from 2,4 - dibromophenol and 5 - chloro - 3 - iso - propylsaligenin; (6) 3-n-propyl-2,21-dihydroxy-5 - bromo - 31,51 - dichlorodiphenylmethane is obtained by reacting 4-bromo-2-n-propylphenol and 3,5-dichlorosaligenin.  The products are of use as antimicrobial constituents of soaps, synthetic detergent compositions (see Group III), rubber goods, plastics, surgical dressings, cosmetics, dentrifices, ointments and creams.ALSO:Germicidal toilet, washing and liquid soaps and synthetic detergent compositions are prepared by incorporating into the composition a 3-alkyl-2:21-dihydroxy-31:5:51-trihalophenyl -methane of the formula <FORM:0698536/III/1> where R is a propyl or a butyl radical and each X represents bromine or chlorine.  Compounds mentioned include 3-isopropyl-2:21-dihydroxy-31:5:51-trichloro - diphenylmethane.  3-sec-butyl-2 : 21-dihydroxy-31 : 5:51-trichlorodiphenylmethane, 3-isopropyl-2:21 - dihydroxy - 51 - bromo - 31:5 - dichlorodiphenylmethane, 3-isopropyl-2:21-dihydroxy-5-chloro-31:51 -dibromodiphenylmethane, p 3-n-butyl-2:21-dihydroxy-31:5:51 -trichlorodiphenylmethane, and 3-n-propyl-2:21 - dihydroxy - 5 - bromo - 31 - 51 - dichlorodiphenylmethane.  In preparing soap compositions the germicide may be added directly to the soap during crutching, milling or a similar operation, or it may be dissolved in a solvent such as alcohol or acetone and the solution dispersed in the soap.  Suitable concentrations of the germicide are from 1 to 3 per cent by weight of the soap.