Patent GB-428142-A (GB)
Title: Manufacture of detergent compounds and their application
IPC: C11D1/42
Filed: 1933-11-06
Abstract: Products useful as detergents are prepared by condensing an alkyl halide having 8 or more carbon atoms with an amine of the formula CnHn + 2(OH)n-1NHR, where n is 5 or and R is hydrogen or a saturated or unsaturated alkyl radicle, e.g. methyl, ethyl, propyl, butyl or allyl.  Such amines are obtainable, as described in Specification 426,062, by treating a monosaccharide containing 5 or 6 carbon atoms with ammonia or a primary amine and hydrogen in the presence of a hydrogenating catalyst; suitable amines are thus obtainable from glucose, arabinose, ribose, lyxose, xylose, gulose, mannose, idose, allose, galactose, altrose, talose and fructose; specified suitable amines are glucamine and its N-methyl and N-ethyl derivatives, N-methylxylamine, N-butylxylamine, N-methylgalactamine, and N-methylfructamine.  As alkyl halides having 8 or more carbon atoms, capryl, lauryl, myristyl, cetyl, stearyl, cerotyl, oleyl, erucyl, linoleyl, linolenyl, and ricinoleyl halides may be used. The reaction may be effected by heating the reagents to 100--200 DEG  C. in the presence of an acid-binding agent, e.g. sodium, potassium or calcium carbonate, sodium or potassium acetate, or magnesium oxide; a solvent may be present, e.g. an alcohol-benzene mixture or aqueous alcohol; a catalyst may also be present, e.g. sodium or potassium iodide.  The products may be converted into salts, e.g. with hydrochloric, sulphuric, phosphoric, acetic or formic acid.  In the examples: (1) N-methylglucamine is condensed with cetyl chloride, prepared from cetyl alcohol, zinc chloride and hydrochloric acid; (2) the product of example 1 is converted into its hydrochloride; (3) N-methylglucamine is condensed with lauryl bromide; (4) glucamine is condensed with cetyl chloride to yield N-cetylglucamine, some N : N-dicetylglucamine being obtained as a by-product; (5) the product of example 1 is converted into its sulphate.  The products may be used as detergents in the textile and leather industries, e.g. for cleaning wool and silk; they may be used in acid aqueous baths or baths containing metal salts such as calcium chloride.  The products may be used in association with other substances, e.g. other detergent, wetting or dispersing agents, or bleaching or disinfecting agents; specified additional substances are turkey red oils; soaps; aromatic sulphonic acids such as alkylnaphthalenesulphonic acids; mineral oil sulphonic acids; sulphonated abietic acid; higher alkyl sulphuric esters; saponin; aliphatic or aromatic acid amides, including sodium taurocholate and salts of analogous amides; neutral or acid salts such as an alkali metal or ammonium sulphate, chloride, bisulphate or bicarbonate, magnesium sulphate, chloride or acetate, or zinc chloride or acetate; persulphates, percarbonates or perborates; fillers or absorbents such as talc, marble dust, starch, clay, or fuller's earth; gum tragacanth; bile acids and their derivatives; agar-agar; gelatin or glue; methyl cellulose; sulphite cellulose lye; calcium saccharate; albumen; sodium cellulose glycollate; natural or synthetic resins; cholesterol derivatives; phosphatides; gelloses; natural or synthetic waxes; wool wax; solvents and softening agents; organic bases and their salts, such as hydroxyalkylamine salts and quaternary ammonium compounds; inorganic colloids; scouring materials such as kieselguhr, pumice powder, sulphur, flour, or china clay; and terpenes or their derivatives such as limonene, dipentene, terpinolene, terpinene, phellandrene, sylvestrene, pinene, bornylene, and sabinene and their alcoholic, ketonic or aldehydic derivatives; perfuming substances may also be present.  A sample has been filed, under Sect. 2 (5), of the product of example 1.  The Specification as open to inspection under Sect. 91 states that R in the formula above may be a substituted alkyl radicle, e.g. hydroxyethyl, dihydroxypropyl, or an alkyl radicle containing a sulphonic or sulphate group.  It refers also to the production of N-cetyl-N-hydroxyethylglucamine and N - cetyl - N - di-hydroxypropylglucamine.  This subject-matter does not appear in the Specification as accepted.ALSO:Products useful as detergents are prepared by condensing an alkyl halide having 8 or more carbon atoms with an amine of the formula Cn Hn+2(OH)n-1NHR, where n is 5 or 6 and R is hydrogen or a saturated or unsaturated alkyl radicle, e.g. methyl, ethyl, propyl, butyl or allyl.  Such amines are obtainable, as described in Specification 426,062, by treating a monosaccharide containing 5 or 6 carbon atoms with ammonia or a primary amine and hydrogen in the presence of a hydrogenating catalyst; suitable amines are thus obtainable from glucose, arabinose, ribose, lyxose, xylose, gulose, mannose, idose, allose, galactose, altrose, talose and fructose; specified suitable amines are glucamine and its N-methyl and N-ethyl derivatives, N-methylxylamine, N-butylxylamine, N-methylgalactamine, and N - methylfructamine.  As alkyl halides having 8 or more carbon atoms, capryl, lauryl, myristyl, cetyl, stearyl, cerotyl, oleyl, erucyl, linoleyl, linolenyl, and ricinoleyl halides may be used. The products may be converted into salts, e.g. with hydrochloric, sulphuric, phosphoric, acetic or formic acid.  In the examples, (1) N - methylglucamine is condensed with cetyl chloride; (2) the product of example 1 is converted into its hydrochloride; (3) N-methylglucamine is condensed with lauryl bromide; (4) glucamine is condensed with cetyl chloride to yield N-cetylglucamine, some N:N-dicetylglucamine being obtained as a by-product; (5) the product of example 1 is converted into its sulphate.  The products may be used as detergents in the textile and leather industries, e.g. for cleaning wool and silk; they may be used in acid aqueous baths or baths containing metal salts such as calcium chloride. The products may be used in association with other substances, e.g. other detergent, wetting or dispersing agents, or bleaching or disinfecting agents; specified additional substances are turkey red oils; soaps; aromatic sulphonic acids such as alkylnaphthalenesulphonic acids; mineral oil sulphonic acids; sulphonated abietic acid; higher alkyl sulphuric esters; saponin, aliphatic or aromatic acid amides, including sodium taurocholate and salts of analogous amides; neutral or acid salts such as an alkali metal or ammonium sulphate, chloride, bisulphate or bicarbonate, magnesium sulphate, chloride or acetate, or zinc chloride or acetate: persulphates, percarbonates or perborates; fillers or absorbents such as talc, marble dust, starch, clay, or fullers earth; gum tragacanth; bile acids and their derivatives; agar-agar; gelatin or glue; methyl cellulose; sulphite cellulose lye; calcium saccharate; albumen; sodium cellulose glycollate; natural or synthetic resins; cholesterol derivatives; p  phosphatides; gelloses; natural or synthetic waxes; wool wax; solvents and softening agents; organic bases and their salts, such as hydroxyalkylamine salts and quarternary ammonium compounds; inorganic colloids; scouring materials such as kieselguhr, pumice powder, sulphur, flour, or china clay; and terpenes or their derivatives such as limonene, dipentene, terpinolene, terpinene, phellandrene, sylvestrene, pinene, bornylene, and sabinene and their alcoholic, ketonic or aldehydic derivatives; perfuming substances may also be present.  The Specification as open to inspection under Sect. 91 states that R in the formula above may be a substituted alkyl radicle, e.g. hydroxyethyl, dihydroxypropyl, or an alkyl radicle containing a sulphonic or sulphate group.  It refers also to the production of N - cetyl - N - hydroxyethylglucamine and N - cetyl - N - dihydroxypropylglucamine.  This subject-matter does not appear in the Specification as accepted.