Patent GB-815784-A (GB)
Title: Cosmetic preparations for the hair
IPC: C07D207/20
Filed: 1955-08-10
Abstract: A cationic detergent preparation for the hair contains (1) a water-soluble quaternary ammonium salt having at least one non-aromatic hydrocarbon residue of more than 7 carbon atoms and, bound to the quaternary nitrogen atom, a residue of the formula <FORM:0815784/III/1> in which R1 represents an alkylene radical containing at most 7 carbon atoms, which may be interrupted by hetero-atoms, particularly oxygen or nitrogen, and R2, R3 each represent hydrogen or an alkyl or substituted alkyl radical containing less than 6 carbon atoms, and (2) a salt of acid reaction or an organic acid.  The non-aromatic hydrocarbon residue may be bound to the quaternary nitrogen atom through an ether, ester or amide group or through a heterocyclic residue such as an imidazoline ring.  The residue of the formula given above is the residue of an aliphatic carboxylic acid amide, for example of caproic acid diethylamide, acetic acid methylamide, and especially acetamide, and the cationic compounds may be prepared by reacting these halogenated amides with a compound containing a non-aromatic hydrocarbon residue of more than 7 carbon atoms, as described above, and a tertiary nitrogen atom.  Several examples of such compounds and preparations are given (see Group IV (b)).  The salt of acid reaction may be a primary phosphate, and the organic acid may be glycolic, citric, acetic or lactic acid.  Other optional ingredients comprise water-soluble non-ionic compounds derived from the condensation of long-chain alkyl mercaptans with an alkylene oxide, fatty acid alkanolamides, e.g. coconut oil fatty acid ethanolamide, phosphoric acid, hydrogen peroxide, acetoacetylaminobenzene, 8-hydroxyquinoline sulphate, bleaching and thickening agents, perfume, and dyestuffs. The products may be made up in solid, paste or liquid form. Specification 793,786 is referred to.ALSO:Quaternary ammonium salts in which there is bound to the quaternary nitrogen atom a residue -R1CONR2R3, where R1 is a C1-7 alkylene group with or without interrupting hetero-atoms and R2 and R3 are hydrogen or C1-5 substituted or unsubstituted alkyl groups, and which also contain at least one non-aromatic hydrocarbon residue of 8 or more carbon atoms bound to the quaternary nitrogen atom through an ester group, an amide group or an imidazoline ring, are prepared by acylating an alkanolamine, a di- or polyamine or an oxyalkylated di-or polyamine with an appropriate non-aromatic carboxylic acid, acid chloride, ester or anhydride, followed, if desired, by alkylation or oxyalkylation (e.g. with ethylene oxide) to provide a product containing a tertiary amino group and either an amide or ester group, and reacting such tertiary amino amide or ester products, or an imidazoline derivative having a C8 or higher hydrocarbon radical and a side chain containing nitrogen (as described in Specification 793,786), with a halogen-carboxylic amide: Halogen-R1-CONR2R3. Preferred products have the formula <FORM:0815784/IV (b)/1> wherein R1 represents C1-5 alkylene (e.g. ethylene or pentamethylene), R2, R3 and R4 represent hydrogen or C1-5 alkyl, R5 and R6 represent C1-5 alkyl (e.g. ethyl or methyl), R7 represents C12-18 alkyl, and the quaternary anion preferably represents chlorine or another halogen but may be exchanged for anions derived from organic or other inorganic acids.  Specified non-aromatic carboxylic acids used for the acylation are capric, lauric, myristic, palmitic, stearic, oleic and linoleic acids. Specified alkanolamines are dimethylethanolamine, dipropylethanolamine and triethanolamine.  Specified di- or poly-amines are ethylene diamine, propylene diamine, hexamethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine and the oxyalkylation products of such amines, e.g. dihydroxyethylethylene diamine and trihydroxyethyl ethylenediamine. The grouping -R1CONR2R3 may be derived, e.g. from acetamide, methylacetamide, or caproic acid diethylamide, the first grouping being introduced, for example, by means of chloracetamide.  In the examples: (1) coconut oil fatty acid is esterified with dimethylethanolamine and the product is treated with chloracetamide; (2) coconut oil fatty acid is condensed with diethylene triamine to yield an imidazoline derivative which is treated with ethylene oxide, whereafter the product is treated with chloracetamide; (3) the imidazoline derivative of Example (2) is treated with propylene oxide and the product is treated with chloracetamide; (4) a reaction product of coconut oil fatty acid and N:N-dimethylpropylene diamine is treated with chloracetamide; (5) a reaction product of stearic acid and N:N-diethylpropylene diamine is treated with chloracetamide.