Patent GB-867874-A (GB)
Title: Improvements in or relating to materials for cleansing the hair
Filed: 1957-09-24
Abstract: Compounds of formula:  Q-NH-CH2-CH2-CH2-NH2 I where Q is a hydrocarbon radical of 12-22 carbon atoms derived from a fatty acid, a rosin acid or a rosin acid derivative are obtained by reacting QNH2 with acrylo-nitrile and catalytically hydrogenating the product. Compounds of formula:  <FORM:0867874/IV (b)/1> where R1, R2, and R3 are -A-COOH or -(C2H2nO)pH A being a saturated straight or branched chain alkylene residue of not more than 3 carbon atoms, n is 2 or 3, p is 1-8, and the average number of CnH2nO groups per molecule is 2-8 and at least one each of the groups -A-COOH and -(CnH2nO)pH is present in the molecule are made (a) by reacting the condensate of QNH2 and acrylo-nitrile with ethylene oxide, catalytically hydrogenating the product and then reacting it with a lower monohalogeno-alkanoic acid in the presence of a hydrohalic acid, or (b) by condensing I with a polyglycol monochlorhydrin, and reacting the product with an alkali metal salt of the appropriate monohalogeno-alkanoic acid, or  (b) by condensing I with an acrylic or methacrylic ester in equimolecular proportions, condensing the product with the desired amount of ethylene oxide and saponifying the condensate.  The amino acids produced by methods (a), (b) and (c) may be freed from alkali metal salts by extracting the neutralized reaction product at pH7 with aryl alcohol or methyl isobutyl ketone, and then removing the solvent.  In Example (I), compound I in which Q is oleyl is condensed with a mixture of ethylene and tetraethylene glycol monochlorhydrins, the mixture neutralized, reacted with sodium monochloracetate and brought first to pH7 by addition of hydrochloric acid, and then to pH4 by addition of acetic acid; (II) compound I in which Q is dehydroabietyl is reacted with methyl methacrylate and the product condensed with ethylene oxide in the presence of Na.OH as catalyst; the ester formed is saponified with NaOH and the mixture brought to pH4 as before; (IV) compound I in which Q is the chain derived from tallow fatty acids is reacted first with ethylene glycol monochlorhydrin, aqueous caustic soda is then added, and the mixture reacted with sodium mono-chloracetate before being neutralized with hydrochloric acid; (V) compound I in which Q is dehydroabietyl is reacted with pentaethylene glycol monochlorhydrin and the product further treated as in (IV); (VI) compound I in which Q is dodecyl is reacted first with methyl methacrylate in aqueous methanol and subsequently with propylene oxide, the methanol, being thereafter distilled off under reduced pressure.  Specifications 437,104 and 823,303 are referred to.ALSO:Homogeneous aqueous shampoo compositions of pH 3-7 comprise ditertiary diamines of formula <FORM:0867874/III/1> where Q is a hydrocarbon radical of 12-22 carbon atoms derived from a fatty acid, a rosin acid or a rosin acid derivative, e.g. a radical derived from oleic or tallow fatty acids or from dehydroabietic acid, and R1, R2 and R3 are selected from -A-COOH and -(CnH2nO)p-H wherein A is a saturated straight or branched chain alkylene residue containing not more than 3 carbon atoms, n is 2 or 3, p is 1 to 8, and the average number of (CnH2nO) groups per molecule is 2-8, at least one each of the groups -A-COOH and -(CnH2nO)p-H being present in each molecule.  Q is preferably an alkyl radical of 12-22 carbon atoms, but may also be an aliphatic hydrocarbon radical the chain length of which corresponds to the average length of the hydrocarbon residues of industrial mixtures of fatty amines of natural or synthetic origin.  The pH of the solution is adjusted by the addition of inorganic or organic acids such as hydrochloric, phosphoric, formic, acetic, propionic, malonic, succinic, glycollic, lactic, glyceric, malic, tartaric or citric acids, and the composition may also include alkanolamides; ethylene oxide adducts with alkylphenols, fatty alcohols, fatty acids, fatty amides and alkanolamides; dyes; and perfumes.  Specifications 437,104 and 823,303 are referred to.