Patent GB-895086-A (GB)
Title: Organic liquids having improved electrical conductivity
IPC: C08F22/00
Filed: 1960-05-25
Abstract: Organic materials having a dielectric constant of 8 or less, e.g. liquid fuels, hydrocarbons, halo-hydrocarbons, ketones, esters, ethers (diethyl ether or dioxane), carbon disulphide, thio-ethers and thio-alcohols, are treated to increase their electrical conductivity by the addition of (a) a salt of a p  polyvalent metal and an alkyl-salicylic acid containing at least one C8+ alkyl group and (b) a soluble polymer or copolymer containing an acidic group or anhydride or salt thereof, the combined proportions of (a) and (b) forming a minor proportion of the composition.  In the component (a) the metal may have an atomic number of 21-29 and is preferably trivalent chromium; the salts may be neutral or basic and may contain phenols and phenates as contaminants from the method of preparation. Amounts equivalent to 1 X 10-9 to 1 X 10-3 gram atom of metal per litre of liquid are added.  Synergistic agents such as calcium dioctylsulphosuccinic acid may also be added, in an amount equivalent to 1 X 10-9 to 1 X 10-4 gram atom of metal per litre.  The component (b) may have a molecular weight of 1 X 104 to 2 X 106 and is preferably formed from monomers, one of which contains a C8+ saturated hydrocarbon group which may contain a hydroxyl group.  The acidic group may be carboxyl, or derived from an oxyacid of sulphur or phosphorus and is preferably introduced by using as a comonomer one of the acids, acrylic, methacrylic, alpha-ethylacrylic, crotonic, isocrotonic tiglic, angelic, vinyl acetic, vinyl propionic, maleic or fumaric. These may be copolymerized with alpha-olefins of at least 10 carbon atoms, e.g. cetene -1 or mixtures thereof obtained by cracking wax, esters of acrylic or methacrylic acids with long chain alcohols, e.g. lauryl or stearyl alcohol or esters of fatty acid, e.g. lauric or stearic acids with vinyl alcohol.  In addition other monomers may be used, e.g. beta-hydroxyethyl methacrylate, beta-diethylaminoethyl methacrylate, 2-methyl-5-vinylpyridine and N-vinylpyrrolidone. Alternatively the acid group may be introduced by partially or completely hydrolyzing ester or nitrile groups in a suitable polymer or copolymer.  If the salt of the acid polymer is used the calcium or nitrogen-base salts may be employed.  Amounts of 0,00001-0,02% of the polymeric material may be added.  A list of specific copolymers is given and the preparation and use of the following are exemplified: (a) Stearylmethacrylate/methacrylic acid (b) beta-hydroxyethyl methacrylate/stearylmethacrylate/methacrylic acid (c) polyethylene imine salt of the copolymer, beta-hydroxy ethyl methacrylate/lauryl methacrylate/stearylmethacrylate/methacrylic acid (d) calcium salt of laurylmethacrylate/methacrylic acid (e) cetene-1/di-n-butyl ester of maleic acid/maleic anhydride.  In examples these polymers are added to gasoline with chromium alkylsalicylate.ALSO:The preparations of the following copolymers are described:  A. Stearylmethacrylate/methacrylic acid.  B. Beta-hydroxyethylmethacrylate/stearylmethacrylate/methacrylic acid. C. Polyethylene imine salt of the copolymer of beta-hyroxyethyl methacrylate/lauryl methacrylate/stearyl methacrylate/methacrylic acid.  D. Calcium salt of the copolymer lauryl methacrylate/methacrylic acid.  E. Cetene-1/di-n-butyl ester of maleic acid/maleic anhydride, (by partial esterification of the cetene/maleic anhydride).ALSO:Organic materials having a dielectric constant of 8 or less, e.g. liquid fuels, hydrocarbons, halohydrocarbons, ketones, esters, ethers (diethyl ether or dioxane), carbon disulphide, thio-ethers and thio-alcohols, are treated to increase their electrical conductivity by the addition of (a) a salt of a polyvalent metal and an alkyl-salicylic acid containing at least one C8+ alkyl group and (b) a soluble polymer or copolymer containing an acidic group or anhydride or salt thereof, the combined proportions of (a) and (b) forming a minor proportion of the composition.  In the component (a) the metal may have an atomic number of 21-29 and is preferably trivalent chromium; the salts may be neutral or basic and may contain phenols and phenates as contaminants from the method of preparation.  Amounts equivalent to 1 X 10-9 to 1 X 10-3 gram atom of metal per litre of liquid are added. Synergistic agents such as calcium dioctylsulphosuccinic acid may also be added, in an amount equivalent to 1 X 10-9 to 1 X 10-4 gram atom of metal per litre.  The component (b) may have a molecular weight of 1 X 104 to 2 X 106 and is preferably formed from monomers, one of which contains a C8+ saturated hydrocarbon group which may contain a hydroxyl group.  The acidic group may be carboxyl, or derived from an oxyacid of sulphur or phosphorus and is preferably introduced by using as a comonomer one of the acids acrylic, methacrylic, alpha-ethyl-acrylic, crotonic, isocrotonic tiglic, angelic, vinyl acetic, vinyl propionic, maleic or fumaric. These may be copolymerised with alpha-olefins of at least 10 carbon atoms, e.g. cetene-1 or mixtures thereof obtained by cracking wax, esters of acrylic or methacrylic acids with long chain alcohols, e.g. lauryl or stearyl alcohol or esters of fatty acids, e.g. lauric or stearic acid with vinyl alcohol.  In addition other monomers may be used, e.g. betahydroxyethyl methacrylate, beta-diethylaminoethyl methacrylate, 2-methyl-5-vinylpyridine and N-vinylpyrrolidone.  Alternatively the acid group may be introduced by partially or completely hydrolysing ester or nitrile groups in a suitable polymer or copolymer.  If the salt of the acid polymer is used the calcium or nitrogen-base salts may be employed.  Amounts of 0.00001%-0.02% of the polymeric material may be added.  A list of specific copolymers is given and the preparation and use of the following are exemplified: (a) Stearylmethacrylate/methacrylic acid (b) beta-hydroxyethylmethacrylate/stearylmethacrylate/methacrylic acid (c) polyethylene imine salt of the copolymer, beta-hydroxy ethyl methacrylate / lauryl methacrylate / stearylmethacrylate/methacrylic acid (d) calcium salt of laurylmethacrylate/methacrylic acid (e) cetene-1/di-n-butyl ester of maleic acid/maleic anhydride.