Patent GB-884775-A (GB)
Title: Hydrazinium salts
Inventor: RUDNER BERNARD
IPC: C07D295/30
Filed: 1959-03-16
Abstract: Stable oil and water emulsions are prepared by the addition of carbon tetrachloride to aqueous solutions of hydrazinium salts of the formula <FORM:0884775/III/1> (wherein R is an alkyl- or alkenyl-amino lower alkyl, alkyl- or alkenyl-carbonylamino lower alkyl, alkyl- or alkenyl-carbonyloxy lower alkyl, saturated or unsaturated aliphatic hydrocarbon or alkycarbonyloxy lower alkylamino lower alkyl radical containing a total of 8 to 24 carbon atoms; or R is an N:N-disubstituted-amino lower alkyl group, the substituents being alkyl, hydroxy lower alkyl, hydroxypoly lower alkoxy lower alkyl, alkyl- or alkenyl-carbonyloxy lower alkyl or alkenylcarbonyl radicals, the total maximum number of carbon atoms being 50; R1 is an aliphatic hydrocarbon, hydroxy lower alkyl, hydroxy lower alkoxy, lower alkyl, hydroxypoly lower alkoxy lower alkyl, alkyl- or -alkenylcarbonyloxy lower alkyl, alkylcarbonylamino lower alkyl or alkylcarbonyloxy lower alkylamino lower alkyl radical containing a total of 1 to 50 carbon atoms; R11 is a lower alkyl, hydroxy lower alkyl, hydroxy lower alkoxy lower alkyl, hydroxypoly lower alkoxy lower alkyl, alkyl carbonyloxy lower alkyl or alkylcarbonyloxy lower alkylamino lower alkyl radical; or R1 and R11 together with the adjacent nitrogen atom form a morpholine ring or a piperazine ring which may be substituted on the free nitrogen atom by an alkanoyl radical: X is a chloride, bromide or iodide ion, and "lower" signifies a radical having 1 to 4 carbon atoms) excluding the hydrazinium chlorides described and claimed in Specification 824,357. Specifications 858,488 and U.S.A. Specifications 2,404,695, 2,678,258 and 2,710,248 also are referred to.ALSO:<FORM:0884775/IV (a)/1> hydrazinium chloride is reacted with tolylene diisocyanate isomers (Nacconate 80) to give a granular polymer, the equation for the formation of which is <FORM:0884775/IV (a)/2> Specification 858,488 and U.S.A.  Specifications 2,404,695, 2,678,258 and 2,710,248 are referred to.ALSO:The invention comprises hydrazinium compounds of the general formula <FORM:0884775/IV (b)/1> wherein R is an alkyl- or alkenyl-amino lower alkyl, alkyl- or alkenyl-carbonylamino lower alkyl, alkyl- or alkenyl-carbonyloxy lower alkyl, saturated or unsaturated aliphatic hydrocarbon of alkylcarbonyloxy lower alkylamino lower alkyl radical containing a total of 8 to 24 carbon atoms; or R is an N : N-disubstituted-amino lower alkyl group, the substituents being alkyl, hydroxy lower alkyl, hydroxypoly lower alkoxy lower alkyl, alkyl- or alkenyl-carbonyloxy lower alkyl or alkenylcarbonyl radicals, the total maximum number of carbon atoms being 50; R1 is an aliphatic hydrocarbon, hydroxy lower alkyl, hydroxy lower alkoxy-lower alkyl, hydroxypoly lower alkoxy lower alkyl, alkyl- or -alkenylcarbonyloxy lower alkyl, alkylcarbonylaminolower alkyl or alkylcarbonyloxy lower alkylaminolower alkyl radical containing a total of 1 to 50 carbon atoms; R11 is a lower alkyl, hydroxy lower alkyl, hydroxy lower alkoxy lower alkyl, hydroxypoly lower alkoxy lower alkyl, alkylcarbonyloxy lower alkyl or alkyl-carbonyloxy lower alkyl amino lower alkyl radical; or R1 and R11 together with the adjacent nitrogen atom form a morpholine ring or a piperazine ring which may be substituted on the free nitrogen atom by an alkanoyl radical; X is a chloride, bromide or iodide ion, and "lower" signifies a radical having 1 to 4 carbon atoms) but excludes the hydrazinium chlorides described and claimed in Specification 824,357.  The chlorides may be prepared by reacting chloramine with the appropriate tertiary amine, or by direct reaction of chlorine, ammonia and the amine, the bromides and iodides being prepared by a metathetical reaction between the hydrazinium chlorides and for example, alkali metal salts of the desired anion.  Esters and amides may be prepared from hydrazinium salts, containing hydroxy or amino groups respectively, and acids. Examples are given and salts of the hydrazinium cations of the invention with anions derived from penicillin, sulphonamides, detergent sulphates, barbiturates and N : N - dimethyldithiocarbamic, hexafluorophosphoric, mercuri-iodic and picric acids are described or referred to.  4 - (Oleoylaminopropyl) - morpholine is prepared from oleic acid and 4-(3-aminopropyl)-morpholine.  4 - Amino - 4 - (2 - hydroxyethyl) morpholinium chloride is prepared from 2 - hydroxyethyl - morpholine and chloramine.  4 - Amino - 4 - (3 - aminopropyl) - morpholinium chloride is prepared similarly, and is converted into a 5-nitrobarbiturate and a tannate.  4 - Stearoyl - 1 - [2 - (stearoylamino) - ethyl] - piperazine is prepared by heating aminoethylpiperazine distearate.  3 - Stearoylaminopropyldimethylamine is prepared by heating stearic acid with dimethylaminopropylamine.  3 - Lauroylaminopropyldimethylamine is prepared similarly.  A mixture of hydroxyethylated diamines of the formula <FORM:0884775/IV (b)/2> (wherein R is the hydrocarbon radical of hydrogenated tallow fatty acids) is prepared by reacting tallowamine with acrylonitrile, reducing the nitrile so formed to the amine RNHCH2CH2 CH2NH2 and reacting this with ethylene oxide A mixture of amines having the structures <FORM:0884775/IV (b)/3> is prepared similarly.  Tetra - (2 - hydroxypropyl) - ethylenediamine is prepared from ethylene diamine and propylene oxide, and is converted to a mono stearate by reaction with stearic acid.  The corresponding mono-oleate is prepared similarly.  1 : 1 - Bis - (2 - hydroxyethyl) - 2 - (oleoyloxy) - ethane is prepared by heating triethanolamine oleate.  Tertiary-butylamine sulphate is prepared by reacting urea with isobutylene to give t-butyl-urea and hydrolysing this with sulphuric acid.  Specification 858,488 and U.S.A.  Specifications 2,404,695, 2,678,258 and 2,710,248 also are referred to.