Patent GB-895895-A (GB)
Title: Process for the manufacture of compounds containing carboxylic amide groups from carbamic and carbonic acid esters
Filed: 1958-12-29
Abstract: Hair-washing compositions comprise cation-active compounds, or acid addition or quaternary ammonium salts thereof, containing at least one carboxylic amide group, at least one amino group and at least one urea group and prepared by heating an acylation product containing at least two amino groups, derived from one molecular proportion of a polyamine and at least one molecular proportion of a C10-18 aliphatic monocarboxyli acid or a functional derivative thereof, with a carbamic acid ester or a carbonic acid ester, and, if desired, converting the product so obtained into a salt by reaction with an acid or a quaternating agent.  The compounds may have the formula <FORM:0895895/III/1> where R is C11-17 aliphatic hydrocarbyl, R1, R2, R3 and R4 are hydrogen or C1-4 aliphatic radicals, especially C2-3 N- hydroxyalkyl, R5 is hydrogen or a residue of formula <FORM:0895895/III/2> where n is 1, 2 or 3 and z is 2 or 3.  The acid addition salts may be derived from, for example, hydrochloric, sulphuric, formic, malic, diglycollic, lactic, citric, tartaric, aminodiacetic or ethylenediaminotetracetic acids.  The compositions advantageously contain alkylene oxide condensates of mercapto compounds containing a non-aromatic residue of at leas 10 carbon atoms. Fatty acid alkanolamides may also be present.  Conventional additives such as perfumes, dyestuffs, blonding agents or thickening agents may be added.  The compositions may be made up as solids, pastes or liquids.ALSO:Compounds, and acid addition salts and quaternary ammonium salts thereof, containing at least one carboxylic amide group, at least one amino group and at least one urea group are prepared by heating an acylation product containing at least two amino groups, derived from one molecular proportion of a polyamine and at least one molecular proportion of an aliphatic monocarboxylic acid containing 10-18 carbon atoms or a functional derivative of such acid, with a carbamic acid ester or a carbonic acid ester, and, if desired, converting the product so obtained into a salt thereof by reaction with an acid or a quaternating agent.  A solvent or catalyst may be present.  The compounds may have the formula <FORM:0895895/IV (b)/1> where R is C11-17 aliphatic hydrocarbyl, R1, R2, R3 and R4 are hydrogen or C1-4 aliphatic radicals, especially C2-3 N-hydroxyalkyl, R5 is hydrogen or a residue of formula <FORM:0895895/IV (b)/2> where n is 1, 2 or 3 and Z is 2 or 3.  The products are used in hair-washing compositions (see Group III).  In examples: ethyl carbamate is reacted with the acylation products of coconut oil fatty acids and N,N1-dihydroxyethyldiethylenetriamine or N-hydroxyethyldiethylenetriamine, and with the acylation product of stearic acid and N,N1-dihydroxyethyltriethylenetetramine; and diethyl carbonate is reacted with the acylation product of coconut oil fatty acids and N,N1-dihydroxyethyldiethylenetriamine.  The acylation products are prepared by condensing the aforementioned reactants in xylene solution in the presence of toluenesulphonic acid.