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  • C10L1/1963—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof mono-carboxylic
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  • C10L1/2437—Sulfonic acids; Derivatives thereof, e.g. sulfonamides, sulfosuccinic acid esters

Definitions

• This invention relates to novel flammable liquid compositions and to novel additives therefor, and particularly to hydrocarbon liquids of increased electrical conductivity.
• Electrostatic charging occurs to a particularly high degree if hydrocarbons are pumped at high speeds.
• Heavy gasolines and kerosenes are often used as jet fuels for aircraft turboprop engines and jet aircraft engines.
• the fuels are generally pumped through relatively narrow hoses which makes it necessary to pump them at high speeds.
• Pumping through filters, as is frequently done when fueling aircraft, may also give rise to high electrostatic charges. It will be clear that in this case the danger of explosions occurring is considerable. However, some danger still exists when hydrocarbons are pumped at lower speeds, such as occurs when storage tanks are filled in refineries, and this danger is greatly increased in the presence of water.
• Belgian patent specification No. 563,850 disclosed the addition of a salt of a polyvalent metal, such as chromium, and an alkylated salicylic acid containing at least 1 alkyl substituent having 8 or more carbon atoms to an organic liquid having a dielectric constant of 8 or less.
• a salt of a polyvalent metal such as chromium
• an alkylated salicylic acid containing at least 1 alkyl substituent having 8 or more carbon atoms to an organic liquid having a dielectric constant of 8 or less.
• a more particular object of the invention is to provide such an additive composition wich can be added to flammable liquids to provide an increase in electrical conductivity of greater permanence in storage. It is a still further object of the invention to provide such an additive composition, which, when added to flammable liquids, will provide an increase in electrical conductivity of greater permanence even in the preesnce of water.
• the said chromium alkyl salicylates may be used together with salts of di-octylsulfosuccinic acid, in particular the calcium salt.
• salts of di-octylsulfosuccinic acid in particular the calcium salt.
• soluble polymers or copolymers directly or indirectly prepared and containing one or more acid groups, including anhydrides or salts of these polymeric compounds, are added to the organic liquids.
• the invention therefore relates to organic liquid compositions having increased electrical conductivity containing a polyvalent metal salt of an alkylated salicylic acid, containing at least one alkyl substituent having 8 or more carbon atoms, and a polymeric material which is soluble in the organic liquid and which contains at least one acid group.
• an acid group is meant a carboxyl group or oxy-acidderived group containing sulfur or phosphorus, and the corresponding anhydrides, and salts of such groups.
• the polymeric compounds of the invention have a stabilizing effect on the electrical conductivity of organic liquids of the above type in which salt of polyvalent metals and an alkylated salicylic acid are present. In many cases they even improve the electrical conductivity of such compositions, It has even been observed that the polymeric compound used in combination with the abovementioned metal salts of alkyl salicylic acid produces an unexpected synergistic effect, in other words, that the electric conductivity of the organic liquid containing both additives is greater than the sum of the electrical conductivities resulting from the use of each of the two additives separately. Another phenomenon observed is that the electrical conductivity of the composition produced according to the invention becomes higher after some time, even in those cases in which they come in contact with water.
• the molecular weight of the polymeric compounds added may be a factor since it has been found that the addition of a polymeric compound having a relatively low molecular weight, for example, 50,000, insures that the maximum electrical conductivity is attained in a shorter period than when a polymeric compound having a relatively high molecular weight, for example, 400,000, is added.
• the molecular weight of the polymeric compounds of the invention may vary within wide limits.
• the molecular weight is preferably at least 1x10 and in particular at least 5X10.
• the molecular weight is preferably not more than 2 l0 and in particular not more than
• the polymeric compound of the invention should be soluble in the organic liquids of which it is desired to increase the electrical conductivity.
• one of the monomers may be an unsaturated carboxylic acid, preferably an unsaturated aliphatic carboxylic acid or an anhydride thereof.
• unsaturated carboxylic acid preferably an unsaturated aliphatic carboxylic acid or an anhydride thereof.
• Readily available commercial acids are acrylic acid and methacrylic acid. It is, however, also possible to use other compounds as starting materials such as alpha-ethylacrylic acid, crotonic acid, isocrotonic acid, tiglic acid, angelic acid, vinyl acetic acid, vinyl propionic acid, maleic acid and fumaric acid. Mixtures of unsaturated carboxylic acids may also be used.
• the unsaturated organic carboxylic acids or anhydrides thereof may be directly or indirectly copolymerized with branched or straight mono-olefins, particularly alphaolefins, having at least 10 carbon atoms or with esters of unsaturated organic carboxylic acids and saturated alcohols or with esters of saturated organic carboxylic acids and unsaturated alcohols, which esters contain a saturated branched or straight carbon chain containing at least 8 carbon atoms.
• This carbon chain may contain one or more polar groups, for example a hydroxyl group.
• alpha-olefins examples include decene, undecene, dodecene, tridecene, tetradecene, pentadecene, hexacene, heptadecene, octadecent, nonadecene, eicosene, heneicosene, docosene, tricosene, tetracosene, pentacosene, hexacosene, heptacosene, octacosene, nonacosene, triacontene, hentriacontene, dotriacontene, tritriacontene, tetratriacontene, pentatriacontene, hexatriacontene, heptatriacontene, octatriacontene, nonatriacontene and tetracontene.
• esters may be esters of an unsaturated carboxylic acid such as acrylic acid or methacrylic acid with primary, secondary or tertiary alcohols having branched or straight carbon chains, for example lauryl or stearyl alcohol or esters of a saturated carboxylic acid for example, lauric acid or stearic acid with an unsaturated alcohol such as vinyl alcohol.
• unsaturated carboxylic acid such as acrylic acid or methacrylic acid
• primary, secondary or tertiary alcohols having branched or straight carbon chains for example lauryl or stearyl alcohol
• esters of a saturated carboxylic acid for example, lauric acid or stearic acid with an unsaturated alcohol such as vinyl alcohol.
• copolymers may be used:
• the polymeric compounds of the invention need not be directly produced, but they may also be indirectly prepared.
• the corresponding compounds containing ester groups or a nitrile group may, for example, first be prepared. They may subsequently be entirely or partly saponified. It is also possible to introduce the acid groups in a polymeric compound.
• the polymeric compounds of the invention are preferably derived from nitrogen-free monomers.
• alkaline earth metal salts particularly the calcium salts of the above-mentioned polymeric compounds may be used and are preferred.
• the salts of monovalent or polyvalent organic nitrogen bases are also suitable for use.
• the polymeric compounds of the invention need only be used in a very small concentration to obtain the desired effect.
• a quantity of, for example, approximately 0.0000l% by weight, preferably at least 0.0002% by weight, added to the organic liquid of which it is desired to increase the electrical conductivity is sufiicient.
• a very suitable quantity is, for example, 0.001% by weight, although larger quantities may also be employed.
• a quantity of not more than approximately 0.02% by weight is generally required for the present object of the invention.
• Salts of a metal with an atomic number higher than 21 and lower than 29 and an alkylated salicyclic acid are preferably used for increasing the electrical conductivity of the organic liquids of the above-mentioned type.
• the alkylated salicylic acid should contain at least 1 alkyl substitutent having 8 or more carbon atoms.
• the number of carbon atoms in the alkyl substituent is preferably between 10 and 22, for example, between 14 and 18.
• other substitucnts may also be present.
• Salts of trivalent metals are preferred.
• Such salts of chromium are elfective for increasing the electrical conductivity of, for example, hydrocarbons.
• the chromium salts may be neutral or basic salts. They may be used in a pure state or may contain contaminations resulting from the preparation, such as phenols and phenates. This preparation is described in the above-mentioned Belgian patent specification.
• concentration of the metal salt of the alkyl salicylic acid required to protect sufiiciently organic liquids such as liquid hydrocarbons against an electrostatic phenomena may be extremely small.
• a concentration of the metal salt equivalent to at least 1 10* gram atoms of the metal per liter of the liquid base is generally sufficient, although l l gram atoms will sufiice in certain cases. Since it is not desirable to employ an excess of the additive in inorganic liquids, such as liquid hydrocarbons, it is preferable to use not more than 1 10- or more preferably at most 1 '10- gram atoms of the metal in the form of the metal salt per liter of the liquid base. Particularly suitable concentrations are in the range of from 1 10- to 1 10' gram atoms of the metal per liter of liquid base.
• the salts of di-octylsulfosuccinic acid are especially suitable for use in combination with the metal salts according to the invention.
• These salts of di-octylsulphosuccinic acid may be employed in quantities in the range of from approximately l to approximately 1 l0 gram atoms of metal per liter, prefenably from l 10-' to 1X10 gram atoms of metal per liter of the liquid base.
• organic liquid is meant single organic liquids as well as mixtures of liquid organic compounds, it being understood that such mixtures may contain components having a dielectric constant of more than 8, provided the dielectric constant of the mixture is 8 or lower.
• the invention is particularly applicable to liquid hydrocarbons. It is of very great importance in connection with volatile organic liquids, for example, organic liquids containing not more than 15, and in particular not more than 12, carbon atoms in the molecule, or liquid mixtures of organic compounds containing an average of not more than 15, and particularly of not more than 12, carbon atoms in the molecule, it being understood that the separate components of such mixtures may contain more than carbon atoms in the molecule.
• volatile organic liquids for example, organic liquids containing not more than 15, and in particular not more than 12, carbon atoms in the molecule, or liquid mixtures of organic compounds containing an average of not more than 15, and particularly of not more than 12, carbon atoms in the molecule, it being understood that the separate components of such mixtures may contain more than carbon atoms in the molecule.
• organic liquids to which the invention is applicable are aliphatic hydrocarbons or mixtures thereof, such as hexane, heptane and corresponding unsaturated hydrocarbons; aromatic hydrocarbons or mixtures thereof, such as ben zene and toluene; cyclic aliphatic hydrocarbons, such as decalin; mixtures of various aliphatic, cyclic aliphatic and aromatic hydrocarbons; halohydrocarbons; ketones; esters; ethers such as diethyl ether and dioxane; carbon disulfide; thioethers and thioalcohols.
• aliphatic hydrocarbons or mixtures thereof such as hexane, heptane and corresponding unsaturated hydrocarbons
• aromatic hydrocarbons or mixtures thereof such as ben zene and toluene
• cyclic aliphatic hydrocarbons such as decalin
• the invention may be particularly applied to light petroleum fractions boiling in the gasoline and kerosene boiling range, for example, fuels for spark-ignition internal combustion engines and fuels for gas turbines used for the propulsion of aircraft. -It may also be applied to such heavier fractions that boil within the gas oil boiling range.
• the polymeric compound A was produced as follows:
• the polymeric compound B was produced as follows:
• the layer containing the desired polymeric compound was poured out in a mixture of 800 parts by weight of methanol and 400 parts by weight of benzene.
• the polymeric compound thereupon separated.
• the yield was 334 parts by weight and the molar ratio of the monomers beta-hydroxy-ethyl methacrylate, stearyl methacrylate and methacrylic acid was 10:2: 1.
• the polymeric compound C was produced as follows:
• the polyethylene-imine salt of this copolymer was prepared. To this end parts by weight of the copolymer were dissolved in 380 parts by weight of benzene and then mixed with a solution of 1.5 parts by weight of polyethylene-imine in 67 parts by Weight of water. The solvents were removed by heating the reaction mixture until a temperature of 125 C. was reached. Any solvent present in the reaction mixture was subsequently removed by evaporation in vacuo at a temperature of 75 C. The yield of the resultant polyethylene-imine salt was parts by weight.
• the polymeric compound D was produced as follows:
• the resultant copolymer containing the monomers lauryl methacrylate and methacrylic acid in a molar ratio of 4:1 was neutralized with calcium hydroxide by adding 0.75 part by weight of calcium hydroxide to 15 parts by weight of copolymer, dissolved in 30 parts by weight of xylene and 2 parts by weight of methanol. After boiling under reflux for one hour the greater portion of the solvents was removed by distillation. The remainder of the solvents was removed by vacuum distillation after filtration of the solution. A yield of 15.3 parts by weight of calcium salt having a calcium content of 1.54% by weight was obtained.
• the polymeric compound E was produced as follows:
• Cetene-l and maleic anhydride dissolved in xylene in a molar ratio of 1:1, were copolymerized at a temperature of 130 C.
• the copolymerization was initiated by adding di-tert. butyl peroxide in a quantity of 0.1% by weight, based on the mixture of the monomers.
• the copolymerization lasted 24 hours.
• a further quantity of 1% by weight di-tert. butyl peroxide was added portionwise to the reaction.
• the resultant copolymer of cetene-l and maleic anhydride which had a molecular weight of 5000 and contained 1 mol of cetene-l per mol of maleic anhydride, was partly esterified with n-butyl alcohol.
• n-butyl alcohol 20 parts by weight of n-butyl alcohol and one part by weight of beta-naphthalene sulfonic acid were added to 50 parts by weight of the resultant copolymer dissolved in 100 parts by weight of benzene.
• the resultant solution was distilled, the water present in the distillate being removed and the remainder of the distillate being continuously returned in the boiling solution.
• the liquid was cooled and washed with water after 0.7 part by weight of water had separated.
• Still another part of the solution of the chromium alkyl salicylate in the gasoline was divided into separate portions.
• a polymeric compound in a quantity of 0.001 by weight was added to each of the portions.
• the polymeric compounds used are mentioned in Table I.
• the electrical conductivity of these portions was measured.
• the change in the electrical conductivity was then determined by again measuring it after 7 days and 35 days.
• a fourth part of the solution of the chromium alkyl salicylate in the gasoline was also divided into separate portions.
• a polymeric compound was added to each of these portions in a quantity of 0.001% by weight, the same polymeric compounds as referred to in the preceding paragraph being used.
• a part of this composition was divided into three portions. A quantity of 0.001% by weight of the polymeric compounds A, C and D was added to each of these portions. The electrical conductivity of these portions was determined. A part of each portion was then intimately mixed with 1% by volume of water. The electrical conductivity of the gasoline layer was determined one day and two days afterwards. Another part of each portion was also intimately mixed with 1% by volume of an aqueous solution containing 30% by weight of sodium hydroxide and 5% by weight of sodium nitrite. The electrical conductivity of the gasoline layer was determined one day and two days afterwards.
• Example III Similar experiments as described in Example II were carried out with a gasoline having an initial boiling point of 80 C. and a final boiling point of 110 C., to which a chromium C -C alkyl salicylate had been added in the quantity indicated in the first paragraph of Example I.
• the polymeric compounds A and C were added in different concentrations to the gasoline and the electrical conductivity of the resultant compositions was measured in a dry and in a wet state.
• the following table summarizes the results obtained.
• An organic liquid composition having increased electrical conductivity consisting essentially of an organic liquid normally having a dielectric constant of not more than 8 and a conductivity additive composition consisting essentially of (1) a salt of a polyvalent metal and an alkylated salicylic acid containing at least one alkyl substituent having eight or more carbon atoms and (2) an organic liquid-soluble nitrogen-free copolymer of an unsaturated aliphatic carboxylic compound, selected from the group consisting of acids, acid anhydrides and alkaline earth metal salts, and from one to three organic comonomers selected from the group consisting of alpha-olefins having at least 10 carbon atoms, esters of unsaturated organic carboxylic acids and unsaturated alcohols and esters of saturated organic carboxylic acids and unsaturated alcohols, said esters containing a saturated aliphatic chain of at least 8 carbon atoms, and said copolymer having a molecular weight of from 1x10 to 2x10 the amount of the additive composition being such as to provide at
• An improved electrical conductivity additive composition consisting essentially of (l) a salt of a polyvalent metal and an alkylated salicylic acid containing at least one alkyl substituent having six or more carbon atoms and (2) an organic liquid-soluble copolymer of an unsaturated aliphatic carboxylic compound, selected from the group consisting of acids, acid anhydrides and alkaline earth metal salts, and from one to three organic comonomers selected from the group consisting of alpha-olefins having at least 10 carbon atoms, esters of unsaturated organic carboxylic acids and saturated alcohols and esters of saturated organic carboxylic acids and unsaturated alcohols, said esters containing a saturated aliphatic chain of at least 8 carbon atoms, and said copolymer having a molecular weight of from 1x 10 to 2 X10 3.
• An improved electrical conductivity additive composition consisting essentially of (1) a salt of a polyvalent metal and an alkylated salicylic acid containing at least one alkyl substituent having at least 6 carbon atoms and 2) a polymeric material according to the polymers recited in claim 1 the salt of the polyvalent metal being present in an amount suflicient to materially increase the conductivity of an organic liquid normally having a dielectric constant of not more than 8, and the amount of the polymeric material being sufiicient to substantially stabilize the electrical conductivity efi'ect of the salt of polyvalent metal.
• composition of claim 1 in which the polymeric material is a copolymer of an unsaturated aliphatic carboxylic acid, an anhydride of an unsaturated aliphatic carboxylic acid and a mono-olefin having an aliphatic chain of at least 10 carbon atoms.
• composition of claim 4 in which one of the monomers of the copolymer is selected from the group consisting of acrylic and methacrylic acids.
• composition of claim 4 in which one of the monomers of the copolymer is selected from the group consisting of maleic and fumaric acids.
• composition of claim 1 wherein the salt of the alkylated salicylic acid contains a metal having an atomic number between 21 and 29.
• composition of claim 7 wherein the metal is chromium.
• composition of claim 1 in which the alkylated salicylic acid contains at least one alkyl substituent having from 10 to 22 carbon atoms.

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