Patent GB-942317-A (GB)
Title: Amino acid salts of detergent sulphates and sulphonates
IPC: C07D207/34
Filed: 1960-06-13
Abstract: The invention comprises compounds of the formula:-<FORM:0942317/C2/1> wherein E is one of the following:- <FORM:0942317/C2/2> <FORM:0942317/C2/3> <FORM:0942317/C2/4> <FORM:0942317/C2/5> <FORM:0942317/C2/6> <FORM:0942317/C2/7> <FORM:0942317/C2/8> <FORM:0942317/C2/9> <FORM:0942317/C2/100> <FORM:0942317/C2/111> <FORM:0942317/C2/122> <FORM:0942317/C2/133>  (13) said radicals (1) to (12) having one or more of the hydrogens of the hydrocarbon groups in the rings thereof substituted by one or more hydroxy and/or alkyl and/or alkylol radicals of 1 to 4 carbon atoms; R represents an organic radical containing at least four carbon atoms, which, if it were connected to a carboxyl group, would provide a monocarboxylic acid; R1 represents hydrogen, C1-4 alkyl, C2-4 alkyl containing one or more hydroxy substituents or C2-4 alkyl containing a single ether or keto linkage therein and optionally substituted by hydroxy groups; R2 represents a C1-4 hydrocarbon group, a C2-4 alkylene group containing one or more hydroxy substituents, a C2-4 alkylene group containing a single ether or keto linkage therein and optionally substituted by hydroxy groups or a phenylene group; Q represents:- <FORM:0942317/C2/144> <FORM:0942317/C2/155>  Y and Y1 each represent -R2-COOM, a C1-12 aliphatic, aromatic or aromatic-aliphatic hydrocarbon radical, a C2-12 hydroxy-substituted aliphatic hydrocarbon radical or a C2-12 aliphatic hydrocarbon radical having at least one ether linkage therein and optionally substituted by hydroxy groups; R3 represents C1-4 alkyl; B represents hydrogen or -R2-COOM; m is o or 1; M is hydrogen or an alkali metal; T represents the hydrocarbon portion of a piperidine, pyrrolidine or pyrrole ring which may bear from 1 to 5 hydroxy and/or C1-5 alkyl and/or C1-5 alkylol substituents, or the oxyhydrocarbon portion of a morpholine ring in which one or more hydrogen atoms may be replaced by hydroxy and/or C1-4 alkyl and/or C1-4 alkylol groups; G represents:- <FORM:0942317/C2/166> or <FORM:0942317/C2/177>  Rf represents a C6-20 aliphatic hydrocarbon radical or an aliphatic-aromatic hydrocarbon radical having a maximum of 20 carbon atoms and at least 6 carbon atoms in the aliphatic portions thereof; Rg represents hydrogen, a C1-8 aliphatic hydrocarbon radical, a hydroxy substituted C1-8 aliphatic hydrocarbon radical, a C2-8 aliphatic ether radical having at least one ether linkage therein or a hydroxy substituted aliphatic ether radical having at least one ether linkage therein; Rh represents an unsubstituted or hydroxy substituted C1-12 aliphatic, aromatic or aromatic-aliphatic hydrocarbon group, a C2-12 aliphatic hydrocarbon having at least one keto linkage therein and optional hydroxy substituents, a C2-12 aliphatic ether radical having at least one ether group therein and optional hydroxy substituents or a C2-12 aliphatic hydrocarbon radical having a CONH or NHCO radical therein; Rk represents an unsubstituted or hydroxy substituted C1-12 aliphatic hydrocarbon radical or a ketone, ether or amide radical as defined for Rh; X represents SO3 or OSO3; M represents hydrogen or an alkali metal; Z represents O or S; and x is 1 to 5. Acids providing R are, for example, saturated, unsaturated and hydroxy substituted fatty acids, aryl-substituted fatty acids such as Twitchell fatty acids, and cycloaliphatic carboxylic acids such as hexahydrobenzoic, resinic and naphthenic acids.  The compounds of the above general formula are prepared by reacting an anionic detergent sulphonate or sulphate of the formula G-M with an amphoteric surface active agent of the formula R-CO-W, wherein W corresponds to the radicals listed for E in which the groups represented by G are replaced by halide or hydroxyl anions.  Starting materials of the formula R-CO-W may be prepared by reacting 1 mol. of an acid R.COOH, or an equivalent amount of the anhydride thereof, with 1 mol. of an appropriate amine, followed by reaction of the resulting amide with appropriate amounts of monohalogen monocarboxylic acids of the formula halogen-R2-COOH and simultaneous or subsequent treatment with an alkali hydroxide. Specification 939,797 is referred to.