Patent GB-428148-A (GB)
Title: Manufacture of detergent compounds and their application
IPC: C11D1/62
Filed: 1933-11-08
Abstract: Soluble quaternary ammonium salts possessing wetting and detergent properties are obtained by treating with an alkyl halide a tertiary amine having the formula CnHn+2 (OH)n-1NR1R2 in which n is 5 or 6 and R1 and R2 are alkyl radicles.  Preferably R1 is a straight chain alkyl radicle having eight or more carbon atoms, and the alkyl halide and R2, which preferably should not contain more than four carbon atoms, may be substituted by hydroxy, sulphonic and sulphate groups. The resulting quaternary ammonium halides may be treated with an inorganic salt which forms an insoluble halide so as to form a quaternary salt of a different inorganic acid or the quaternary ammonium halide may be first converted into the quaternary ammonium hydroxide and then treated with an organic acid, e.g. acetic, formic, or benzoic acid or an inorganic acid, e.g. sulphuric, sulphurous or phosphorous acid. The tertiary amines may be prepared according to the process of Specification 428,142 by treating secondary amines with a higher alkyl halide or by reacting monosaccharides containing five or six carbon atoms with secondary amines and hydrogen as described in Specification 426,062.  In examples: (1) N - methyl - N - ethyl - N - glucylcetylammonium iodide is obtained by reacting cetyl chloride with N-methyl-glucylamine in the presence of sodium carbonate, a trace of potassium iodide and a 1 : 1-alcohol-benzene mixture to form N-methyl-N-glucylcetylamine and treating the latter with ethyl iodide; the cleansing power of the product is tested when dissolved in water containing calcium chloride, sulphuric acid and sodium carbonate; (2) methyl iodide or ethyl bromide is reacted with N-methyl-N-glucylcetylamine. N-Methyl-N-ethyl-N-glucylcetyl ammonium chloride or sulphate, N-methyl-N-glucyl-N-cetylhydroxyethylammoniumiodide; N-methyl-N-ethyl-N-glucyl laurylammoniumbromide, N-methyl-N-ethyl - N - glucylstearylammonium iodide, N : N - dimethyl or ethyl - N - glucyloleyl - ammonium chloride, N - methyl - N - ethyl - N - xylylcetylammoniumiodide, N-ethyl-N-butyl-N-xylylcetylammoniumbromide, N-methyl- or -ethyl-N-galactyloleylammoniumiodide, N : N-diethyl - N - fructylcetylammoniumchloride and N - methyl - N - (1 - propane - 2 : 3 - diol) - N - glucylcetylammoniumiodide are specified products. They may be used with any wetting, washing, emulsifying, absorbing, lathering, bleaching, germicidal or bactericidal compounds, e.g. di or trisodium phosphate, turkey red oils, soaps, aromatic or mineral oil sulphonic acids sulphonated abietic acid, higher alkylsulphuric esters, saponin, aliphatic and aromatic acid amides such as sodium taurocholate, sodium sulphate, chloride or acetate, magnesium sulphate, chloride or acetate, zinc chloride or acetate, persulphates, percarbonates, perborates, talc, marble dust, starch, fuller's earth, gum tragacanth, gallacids, agar-agar, glue, methylcellulose, sulphite cellulose lyes, sodium cellulosephthalate, calcium saccharate, albumin, sodium cellulose glycollate, gelatin, natural and artificial resins and waxes, cholesterine derivatives, phosphatides, geloses, solvents, perfumes, softening agents, hydroxyalkylamine salts, inorganic colloids, scouring material, e.g. pumice powder, sulphur flour, china clay and salt, limonene, dipentene, terpinolene, phellandrene, sylvestrene, pinene, bornylene, sabinene and alcoholic, ketonic and aldehyde derivatives of these terpenes.  The Specification as open to inspection under Sect. 91 comprises also the use of any aliphatic inorganic ester in place of the alkyl halide for the treatment of the tertiary amines. Diethyl-and dimethyl sulphate are mentioned.  Products may also be obtained containing hydroxy, sulphonic and sulphate groups.  This subject-matter does not appear in the Specification as accepted.ALSO:Soluble quaternary ammonium salts possessing detergent properties are obtained by treating with an alkyl halide a tertiary amine having the formula CnHn+2(OH)n-1NR1R2, in which n is 5 or 6 and R1 and Rs are alkyl radicles. Preferably, R1 is a straight chain alkyl radicle having eight or more carbon-atoms, and the alkyl halide and R2, which preferably should not contain more than four carbon atoms, may be substituted by hydroxy, sulphonic and sulphate groups. The resulting quaternary ammonium halides may be treated with an inorganic salt which forms an insoluble halide so as to form a quaternary salt of a different inorganic acid or the quaternary ammonium halide may be first converted into the quaternary ammonium hydroxide and then treated with an organic acid, e.g. acetic, formic, or benzoic acid or an inorganic acid, e.g. sulphuric, sulphurous or phosphorus acid.  The tertiary amines may be prepared according to the process of Specification 428,142 by treating secondary amines with a higher alkyl halide or by reacting monosaccharides containing five or six carbon atoms with secondary amines and hydrogen as described in Specification 426,062.  In examples: (1) N-methyl-N-ethyl-N-glucylcetylammonium iodide is obtained by reacting N - methyl - N - glucylcetylamine with ethyliodide; the cleansing power of the product is tested when dissolved in water containing calcium chloride, sulphuric acid and sodium carbonate; (2) methyl iodide or ethyl bromide is reacted with N-methyl-N-glucylcetylamine. N - Methyl - N - ethyl - N - glucylcetylammonium chloride or sulphate, N-methyl-N-glucyl-N-cetyl - hydroxyethylammoniumiodide; N - methyl-N-ethyl-N-glycyl lauryl-ammoniumbromide, N-methyl-N-ethyl-N-glucylstearyl-ammoniumiodide, N:N-dimethyl or ethyl-N-glucyloleylammoniumchloride, N-methyl-N-ethyl - N - xylylcetylammoniumiodide, N-ethyl-N - butyl - N - xylylcetylammoniumbromide, N-methyl - N - ethyl - N - galactyloleylammonium-iodide, N:N-diethyl-N-fructylcetylammonium-ehloride and N-methyl-N-(1-propane-2 : 3-diol)-N - glucylcetylammoniumiodide are specified products.  They may be used with any wetting, washing, emulsifying, absorbing, lathering, bleaching, germicidal or bactericidal compounds, e.g. di or trisodium phosphate, turkey red oils, soaps, aromatic or mineral oil sulphonic acids, sulphonated abietic acid, higher alkyl-sulphuric esters, saponin, aliphatic and aromatic acid amides such as sodium taurocholate, sodium sulphate, chloride or acetate, magnesium sulphate, chloride or acetate, zinc chloride or acetate, persulphates, percarbonates, perborates, talc, marble dust, starch, fuller's earth, gum tragacanth, gall acids, agar-agar, glue, methyl-cellulose, sulphitecellulose lyes, sodium cellulosephthalate, calcium saccharate, albumin, sodium cellulose glycollate, gelatin, natural and artificial resins and waxes, cholesterine derivatives, phosphatides, geloses, solvents, perfumes, softening agents, hydroxyalkylamine salts, inorganic colloids, scouring material, e.g. pumice powder, sulphur flour, china clay and salt, limonene, terpinolene, phellandrene, sylvestrene, pinene, bornylene, sabinene and alcoholic, ketonic and aldehyde derivatives of these terpenes.  The Specification as open to inspection under Sect. 91 comprises also the use of any aliphatic inorganic ester in place of the alkyl halide for the treatment of the tertiary amines. Diethyl and dimethyl sulphate are mentioned.  The products may also contain hydroxy, sulphonic and sulphate groups.  This subject-matter does not appear in the Specification as accepted.