Patent GB-857097-A (GB)
Title: Improvements relating to benzyl dithiocarbamates and their use in bacteriostatic products
Inventor: GARMAISE DAVID L
IPC: C07C333/20
Filed: 1958-03-03
Abstract: Paints contain as bacteriostatic agents compounds of the general formula: <FORM:0857097/IV(a)/1> wherein the symbols X represent hydrogen or chlorine atoms or nitro groups at least one X on each ring being a chlorine atom or a nitro group.  Examples relate to the preparation of a latex paint containing pigment, 4-chlorobenzyl 3, 4-dichlorobenzyl dithiocarbamate, butadienestyrene copolymer latex, starch solution, alkyl phenol-ethylene oxide condensate, water and anti-foam agent; exterior flat paint containing ester gum, bodied linseed oil, pine oil, cobalt naphthenate, lead naphthenate, boiled linseed oil fatty acids, casein, 3,4-dichlorobenzyl 3,4-dichlorobenzyldithiocarbamate, 2-amino-2-methyl 1-propanol and water, pigment, lithopone and diatomite and a semigloss latex paint containing titanium dioxide, lithopone, mica, water, wetting agent, tetra-sodium pyrophosphate, soya bean protein, ammonium hydroxide, 4-chlorobenzyl 3, 4-dichlorobenzyl dithiocarbamate, sodium alginate and butadiene-styrene copolymer latex.ALSO:The invention comprises compounds of the general formula:  <FORM:0857097/IV(b)/1> wherein X represents hydrogen or chlorine atoms or a nitro group, at least one X on each ring being a chlorine atom or a nitro group, and a process from the preparation thereof wherein a substituted benzylamine of the formula:  <FORM:0857097/IV(b)/2> wherein X represents hydrogen or chlorine atoms or nitro groups and at least one X is a chlorine atom or a nitro group, is reacted with carbon disulphide and a tertiary amine in an inert solvent, and thereafter a solution of the tertiary amine salt of the substituted benzyl dithiocarbamic acid thus produced is refluxed with a benzyl chloride of the general formula: <FORM:0857097/IV(b)/3> where X has the meaning assigned to it above. Solvents mentioned include diethyl ether, petroleum ether, benzene and chloroform. Examples are furnished relating to the production of 2, 4-dichlorobenzyl-4-chlorobenzyl dithiocarbamate; 3, 4-dichlorobenzyl 4-chlorobenzyl dithiocarbamate; 4-chlorobenzyl 2, 4-dichlorobenzyl dithio carbamate; 2, 4-dichlorobenzyl 2, 4-dichlorobenzyl dithiocarbamate; 3, 4-dichlorobenzyl 2, 4-dichlorobenzyl dithiocarbamate; 4-chlorobenzyl 3, 4-dichlorobenzyldithiocarbamate, 2, 4-dichlorobenzyl, 3, 4-dichlorobenzyldithiocarbamate, 3, 4-dichlorobenzyl, 3, 4-dichlorobenzyldithiocarbamate; 4-chlorobenzyl 4-nitrobenzyldithiocarbamate; 2, 4-dichlorobenzyl 4-nitrobenzyldithiocarbamage, 3, 4-dichlorobenzyl 4-nitrobenzyldithiocarbamate and 4-nitrobenzyl, 3, 4-dichlorobenzyldithiocarbomate.  The tertiary amine specified in triethylamine.  The products are bacteriostatic agents and are used in paints (see Group IV(a)) and soaps (see Groups III and VI).ALSO:Saponaceous compositions comprise as bacteriostatic agents compounds of the general formula:  <FORM:0857097/III/1> wherein the symbols X represent hydrogen of chlorine atoms or nitro groups, at least one X on each ring being a chlorine atom or a nitro group (see Group IV(b)).  A liquid soap formulation containing 4-chlorobenzyl 3,4-dichlorobenzyl dithiocarbamate, ethanol and an aqueous solution of soap obtained by the saponification of coconut oil with potash and a germicidal bar soap prepared from soap containing coconut oil fatty acids and a dithiocarbamate selected from the products of examples, representative of which are 4-chlorobenzyl 2,4-dichlorobenzyl dithiocarbamate and 4-chlorobenzyl 4-nitrobenzyl dithiocarbamate, are described.ALSO:A bacteriostatic composition comprises a compound of the formula:  <FORM:0857097/VI/1> wherein the symbols X represent hydrogen or chlorine atoms or nitro groups, at least one X on each ring being a chlorine atom or a nitro group (see Group IV (b)) and a carrier substance e.g. a soap.  A liquid soap formulation containing 4-chloro-benzyl 3, 4- dichlorobenzyl dithiocarbamate, ethanol and an aqueous solution of soap obtained by the saponification of coconut oil with potash and a germicidal bar soap, prepared from soap containing coconut oil fatty acids and a dithiocarbamate selected from the products of examples, representative of which are 4- chlorobenzyl 2, 4- dichlorobenzyl dithiocarbamate and 4- chlorobenzyl 4-nitrobenzyl dithiocarbamate are described.