Patent GB-838018-A (GB)
Title: Improvements in or relating to the preservation of soap compositions
Inventor: HOLNESS DOUGLAS
IPC: C11D10/04
Filed: 1956-08-28
Abstract: Soap compositions contain, as a preservative, a hydrazone of the general formula RXNH.N = CR1R2 where R and R1 are alkyl, aryl, or aralkyl groups, R2 is hydrogen, alkyl, aryl or aralkyl, R contains not more than 20 carbon atoms, and X is either -CO- or -SO2-; R, R1 and R2 may be substituted with such substituents as do not confer odour, colour, or instability on the molecule, for example hydroxyl, alkoxyl or halogen, and may in addition be unsaturated.  The molecule may also contain a further substituent group -XNH.N = CR1R2, and the groups R1 and R2 may be joined to form a ring; R1 and R2 together preferably contain not more than 20 carbon atoms, and the hydrozones preferably have molecular weights of 150-500.  The hydrazones are incorporated in soap (which may contain resin soaps) in amounts of up to 5%, generally 0.1-1%.  Several examples of suitable hydrazones are given, together with preparative details (see Group IV (b)).ALSO:Hydrazones of the general formula RXNH N=CR1R2, where R and R1 are alkyl, aryl or aralkyl groups, R2 is hydrogen, alkyl, aryl or aralkyl, R contains not more than 20 carbon atoms, and X is either -CO- or -SO2, are prepared by the reaction of acyl or sulphonyl hydrazines RCONHNH2 or RSO2NHNH2 with the aldehydes or ketones R1COR2.  R, R1 and R2 may be substituted p  with substituents such as alkoxyl, hydroxyl, or halogen and may be saturated or unsaturated. The molecule may also contain a further substituent group -XNH.N=CR1R2, and the groups R1 and R2 may be joined to form a ring; R1 and R2 together preferably contain not more than 20 carbon atoms. The hydrazones, which preferably have molecular weights of 150-500, are used as soap preservatives (see Group III).  The preparation of the following hydrazones is described.  (a) N - lauroyl - N1 - heptylidene hydrazine, C11H23CONH.N=CH.C6H13 is obtained by the condensation of n-heptaldehyde with lauroyl hydrazine in boiling ethanol, followed by recrystallization from ethanol.  (b) N - (g  - hydroxybutyryl) - N1 - isopropylidene hydrazine, HOCH2(CH2)2CONH.N= C(CH3)2 is obtained by refluxing g -hydroxybutytyl hydrazine (obtained by condensing together hydrazine hydrate and g -butyrolactone) with excess acetone, and recrystalling the product from benzene-acetone.  (c) N - lauroyl - N1 - (a  - amylcinnamylidene) - hydrazine, C11H23CO.NH.N=CH. C(C5H11)=C6H6 is obtained by condensing lauroyl hydrazine with a -amylcinnamaldehyde in boiling ethanol.  (d) N - (p - toluenesulphonyl) - N1 - (2 : 3 : 4 : 5 : 6 - pentahydroxyhexylidene) hydrazine, CH3.C6H4.SO2.NH.N= CH.(CHOH)4.CH2OH is obtained by condensing p-toluenesulphonyl hydrazine with glucose in aqueous methanol, followed by recrystallization from aqueous methanol.  (e) N - (g  - hydroxybutyryl) - N1 - (anisylidene) hydrazine, HOCH2(CH2)2CO.NH.N= CH.C6H4.OCH3 is obtained by reacting the intermediate of (b) with anisaldehyde and recrystallizing from aqueous methanol.  (f) N - (g - hydroxybutyryl) - N1 - (cyclohexylidene) hydrazine, HOCH2.(CH2)2CO.NH. N=C6H10, is obtained by reacting the intermediate of (b) with cyclohexanone and recrystallizing from benzene.  (g) Di - isopropylidene tartaric dihydrazide, (CH3)2C = N . NH . CO(CHOH)2CO . NH . N= C(CH3)2 is obtained by reacting with excess acetone the intermediate (tartaric dihydrazide) obtained by refluxing together diethyl tartrate and hydrazine hydrate.