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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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  • C10L1/2283—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles containing one or more carbon to nitrogen double bonds, e.g. guanidine, hydrazone, semi-carbazone, azomethine
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Definitions

• the conductivity imparted to the liquid by the conductivity additive is much more permanent than in the case of the higher concentrations.
• concentration is l l0 gram atom of metal per liter of flammable liquid, or less
• conductivity benefit is retained for many days in storage.
• conductivity benefit is gradually and sometimes very rapidly decreased, often to a level which is only a small fraction of the initial value.
• composition of the invention is thus a conductivity additive composition (or a flammable liquid containing it) comprising substantial proportions each of (l) a salt of a metal having an atomic number from 22 through 28 and a relatively high molecular weight aromatic carboxylic or sulfonic acid, and (2) a copolymer as described above.
• conductivity additive or a flammable liquid containing it
• a conductivity additive composition comprising substantial proportions each of (l) a salt of a metal having an atomic number from 22 through 28 and a relatively high molecular weight aromatic carboxylic or sulfonic acid, and (2) a copolymer as described above.
• the metal salt conductivity additive in the compositions of the invention is oil soluble and has a molecular weight of at least 200, preferably at least 500, preferably no more than 3000, especially up to about 2500.
• a xylene solution of the carboxylate may be freed from xylene by steam distillation, acidified and extracted with dilute ammonia solution.
• Another method consists in acidifying the carboxylate, and neutralizing it with an alkali metal hydroxide, whereby the alkylsalicylic acids are converted into the alkali metal salts and the alkylphenols remain unconverted; from a solution of a mixture of alkali metal salts of alkylsalicylic acids and alkylphenols in a wateralcohol mixture (e.g. 50% aqueous isopropanol) the alkyl phenols can be extracted by means of a liquid aliphatic hydrocarbon, such as pentane.
• a liquid aliphatic hydrocarbon such as pentane.
• product E-l has a chromium content of 4.78% by weight.
• a special advantage of the chromium salts as conductivity additives in the present invention is due to'the fact that they are not leached from hydrocarbon solutions by water. This is shown in this example.
• Concentrations of suchsynergists are suitably from about 1X10 to about 1 1()- mol per liter, preferably about 1, 10- to about 1 10- mol per liter, .of the flammable liquid.
• the oil-soluble nitrogen-containing copolymer can be selected from a very wide class of such compounds.
• Preferred such copolymers are the copolymers :of a vinylpyridine and at least one ester of an acrylic ;acid and a long chain aliphatic alcohol containing at Eleast carbon atoms, as described in Barnum et al., US. 2,839,512, June 17, 1958.
• the disclosure of this patent is incorporated herein by reference for a complete description of the preferred copolymers.
• oil-soluble nitrogen-containing copolymers particularly suitable in the compositions of the invention are the oil-soluble, basic amino nitrogen-containing addition-type polymers of a plurality of polymerizable ethylenically unsaturated compounds, at least one of which is amine-free and contains from 8 to about 18 carbon atom in an aliphatic hydrocarbon chain which is a side chain in the polymer, and one of which contains a basic amino nitrogen atom in a side chain, as described in Catlin et al,, US. 2,737,452, March '6, 1956.
• the disclosure of this patent is incorporated herein by reference for a complete description of such suitable copolymers.
• Preferred such basic amino nitrogen-containing copolymers are those in which the amino compound is a dialkylaminoalkyl acrylate such as diethylaminoethyl methacrylate,for example the threecomponent copolymer of lauryl methacrylate styrene and diethylaminoethyl methacrylate (45 :45: 10 ratio).
• the amino compound is a dialkylaminoalkyl acrylate such as diethylaminoethyl methacrylate,for example the threecomponent copolymer of lauryl methacrylate styrene and diethylaminoethyl methacrylate (45 :45: 10 ratio).
• oil-soluble nitrogen-containing copolymers particularly suitable in the compositions of the invention are the copolymers of an N-vinyl-Z-pyrrolidone and at least one C (average)-alkyl ester of an acrylic acid, as described in the Belgian patent to Rohm and Haas Company, Belg. 550,442, or in the Canadian patent to Sachs, Can. 560,549, July 22, 1958. Again for the sake of brevity, the disclosures of these patents, too, are incorporated herein by reference for a complete description of such suitable copolymers.
• copolymers are those of N-vinyl-2-pyrrolidone itself and a mixture of alkyl methacrylates the alkyl (esterifying) groups of which are obtained from a commercial mixture of C to C primary alcohols, in which copolymer the 'acids and the long chain aliphatic alcohols.
• ratio of the N-vinyl pyrrolidone structure to the methacrylate ester structure is about 1 to 5 or 6.
• Still other oil-soluble nitrogen-containing copolymers particularly suitable in the compositions of the invention are the copolymers of an alpha olefin having at least 10 carbon atoms and an ester of an acrylic acid and a C alianol, at least 10% of the ester groups of which copolymers have been amidized with an amine containing a substituent polar group, especially NR or Where R is a hydrocarbyl group, as described in Bondi et al., US. 2,800,452, July 23, 1957. Again for the sake of brevity, the disclosure of this patent, too, is incorporated herein by reference for a complete description of such suitable copolymers.
• Still other oil-soluble nitrogen-containing copolymers particularly suitable in the compositions of the invention are the copolymers containing (A) at least one oil-solubilizing compound having an ethylenic linkage and a group of 4 to 30 aliphatic carbon atoms and which is copolymerizable through said linkage and (B) at least one amide of an alpha, beta-unsaturated carboxylic acid of from 3 to 6 carbon atoms, with from 1 to .15 units of the ethylenic component (A) being present in the copolymer for each unit of the amide component (B), as described in the British patent to California Research Corporation, Br. 759,517, published October 17, 1956. Again for the sake of brevity, the disclosure of this patent, too, is incorporated herein by reference for a complete description of such suitable copolymers.
• the oil-soluble nitrogen-containing copolymers should have molecular weights in the range 5000 to 2,500,000 as determined by the light scattering technique described in Chem. Rev., vol. 40, page 319 (1948), preferably from 50,000 to 1,000,000, or most especially from 100,000 to 650,000.
• the nitrogen content of the copolymer is important; it should be at least 0.1% by weight of the copolymer and preferably not more than 8%, but more especially at least 1% and not more than 5% by Weight the copolymer having an inherent viscosity of from about 0.1 to 3.0 as determined at 0.1% weight volume concentration in benzene at 25 C.
• a particularly preferred class of copolymers for the purposes of the present invention are copolymers of the type described in the above Barnum et al. patent but which also contain, as one ofthe monomers, an ester of an acrylic acid and a lower alkanol, viz., special copolymers of 1) a vinylpyridine, (2) a mixture of at least two dissimilar esters of an acrylic acid and long chain alcohols containing at least a pair of esters derived from alcohols which diflFer by at least 4 carbon atoms and which are present in a mol ratio to one another of from 1:10 to 10:1, and (3) at least one ester of an acrylic acid and a lower alkanol containing no more than 6 carbon atoms, such as methyl .methacrylate or butyl methacrylate, in which copolymer the mol ratio of the vinylpyridine to the esters is from 1:15 to 2:1 and the lower alkyl ester is from lO-to 75 mol percent of the total esters.
• the vinylpyridines used in making these special copolymers may be exemplified by 2-vinylpyridine, 3-vinylpyridine, 4-vinylpyridine, 2-methyl-5-vinylpyridine, 4- methyl-Z-vinylpyridine, S-ethyl-Lvinylpyridine and butyl-S-vinylpyridine, and the like.
• Particularly preferred groups comprise 2-, 3- and 4-vinylpyridines and the lower alkyl-substituted derivatives thereof.
• the long chain acrylate esters used in the preparation of these special copolymers include the esters of acrylic
• the acrylic acids include acrylic acid and the alphasubstituted acrylic acids such as methacrylic acid, ethacrylic acid, alpha-phenyl acrylic acid, alpha-cyclohexyl acrylic acid and chloroacrylic acid.
• the long-chain'aliphatic alcohols used in the esterification of these acids may be exemplified by decyl, lauryl, cetyl, stearyl, eicosanyl, nonadecanyl, and the like alcohols and mixtures thereof.
• Particularly preferred esters to be used are the acrylic acid and methacrylic acid esters of aliphatic monohydric alcohols, and especially alkyl alcohols, containing from 14 to 20 carbon atoms.
• these long chain acrylic acid esters include, among others, decyl acrylate, lauryl acrylate, stearyl acrylate, decyl methacrylate, lauryl methacrylate, cetyl methacrylate, stearyl methacrylate, eicosanyl acrylate, docosanyl acrylate and the like, and mixtures thereof.
• a mixture of two or more of these long chain acrylate esters is used in making the new copolymers.
• Illustrative examples of these mixtures include, among others dodecyl methacrylate/octadecyl methacrylate, tetradecyl acrylate/octadecyl methacrylate, decyl methacrylate/octadecyl methacrylate, tetradecyl methacrylate/ hexadecyl methacrylate, tetradecyl acrylate/octadecyl methacrylate, dodecyl methacrylate/eicosanyl acrylate, and the like.
• an ester of acrylic acid or methacrylic acid and technical lauryl alcohol which is a mixture of straight chain alcohols, should not be considered such a mixture as described above since copolymers of lauryl (technical) methacrylate and a vinylpyridine will not havethe required ratio of dissimilar alkyl chains or the average alkyl chain length which is required of such preferred special copolymers.
• the third type of component used in making these special copolymers is an ester of an acrylic acid and a lower aliphatic alcohol of not more than 6 carbon atoms.
• these lower acrylates include, among others, the acrylic acid and methacrylic acid esters of methanol, ethanol, butanol, hexanol, isobutyl alcohol and propanol.
• This third component is used only in certain specific amounts. It has been found that the ester of the acrylic acids and the aliphatic alcohol containing not more than 6 carbon atoms should be employed in no more than 75 mol percent of the total acrylate ester mixture, i.e. the total of the mixture of long chain esters and the lower aliphatic monohydric alcohol containing not more than 6 carbon atoms. Preferably the lower acrylate ester is employed in amounts varying from 15% to 60% by weight of the total acrylate ester mixture.
• EXAMPLE VI A mixture of 2.52 mol of stearyl methacrylate, 5.04 mol of lauryl methacrylate, 0.83 mol of methyl methacrylate and 1 mol of Z-methyl-S-vinyl pyridine and 0.2% wt. of alpha, alpha aodiisobutyronitrile dissolved in a minor amount of acetate for solubility was placed in a reaction vessel and reacted for about 2448 hours at 65 C. with stirring in a nitrogen atmosphere. The polymer was then dispersed in equal volumes of benzene and thereafter precipitated with 5-10 volumes of a mixture of acetone and methanol.
• SMA stearyl methacrylatc
• LMA laury1 mcthacrylate
• MMA methyl mcthaerylate
• BMA butyl methacrylate
• MVP 2-methyl-5- viuylpyridinc EVP fi-ethyhZ-viuylpyridine.
• EXAMPLE XXI 29.3% stearyl methacrylate, 49.7% lauryl methacrylate, 16% methyl methacrylate and 5.0% methyl Vinylpyridine were charged to a 300-gallon stainless steel autoclave. A 50/ 50 mixture of benzene and neutral petroleum oil was then added to the autoclave so as to furnish 1 part of the mixture per 3 parts of the total monomer. 0.25% of ditert-butyl peroxide was then added and the mixture heated at 120 C. for about seven hours. At the completion of the reaction, the benzene was stripped off to final conditions of 120 C. and 10 mm. Hg with nitrogen sparging. The benzene-free product was then diluted with neutral oil to a polymer content of about 30% by weight and filtered at 120 C.
• the conductivity additive composition of the invention must contain very substantial amounts of the copolymer in proportion to the metal salt. It is generally necessary that the weight ratio of copolymer to metal in the metal salt conductivity additive be at least 20:1, more especially at least 50:1, and preferably even at least 200:1. On the other hand it will rarely be necessary that a weight ratio greater than 5000:1 of copolymer to metal in the metal salt be used, and, in order to minimize water sensi tivity of hydrocarbon liquids, especially fuels, into which the composition is incorporated, it is desirable that this ratio be no greater than 2000:1. It .is particularly preferred that this ratio be no greater than 1500:1.
• Suitable hydrocarbon base liquids into which the conductivity additive composition'of the invention can be advantageously incorporated are those normally boiling Within the range of from about -40 F. to about 700 F., i.e., those which are generally referred toas hydrocarbon distillates.
• the invention is particularly applicable to petroleum distillates in the gasoline and kerosene boiling ranges, such as gasoline (both automotive and aviation), aviation turbine fuel of the JP-l, JP4 and JP-S mineral spirits, rubber solvent, lacquer diluent, insecticide base, kersosene, and special boiling range solvents of all kinds such as direct cuts of xylenes and non-aromatics boiling in or near the xylene range, or similar toluene or benzene cuts, and also extracts and rafiinates (e.g. from S or furfural extraction) obtained from such cuts.
• the invention is of greatest benefit and importance in the case of aviation turbine fuels, especially of the kerosene type, because of the extreme danger of static electrical charges in such fuels.
• the concentration of the metal-containing salt necessary to adequately protect a hydrocarbon liquid from electrostatic phenomena is extremely minute. In general it is only necessary to provide in the hydr0- carbon liquid a concentration of the metal salt equivalent to at least l lO gram atom of the metal per liter of the hydrocarbon liquid, although in some cases no more than 1X 10* gram atom will be needed. On the other hand, because it is not desirable to incorporate in a hydrocarbon liquid too much of an ash-containing additive, it is preferred to use no more than l 10- or preferably no more than 1 10 gram atom of the metal in the form of the metal salt per liter of hydrocarbon liquid.
• Especially suitable concentrations are from about 1X10 to about 1 l0- gram atom of the metal per liter of hydrocarbon liquid.
• concentrations for example 1 l() to l 10- gram atom of metal.
• the conductivity benefits while relatively smaller are nevertheless relatively well retained by the hydrocarbon liquid.
• Example IV where there was no loss of conductivity in the case of 1X 10 mols and even 1X l0 mols chromium per liter of gasoline after 4 days.
• the loss became very significant at 1X 10* mols chromium per liter of gasoline, and as will be shown in Example XXII below, becomes very large in the case of higher concentrations and in a heavier hydrocarbon liquid.
• Fuel composition B thus contained the copolymer and metal of the metal salt conductivity additive in a weight raito of copolymer to metal (i.e., chromium) of about 450:1.
• R is an alkylene radical containing from 1 through 4 carbon atoms, preferably ethylene or 1,2-propylene.
• metal deactivators thus include, and are preferably, the compounds described in Downing et al., US. 2,181,121, November 28, 1939, and in White et al., US. 2,285,878, June 9, 1942. It is preferred that the metal deactivators, except for the oxygen and nitrogen atoms in the above structural group, be entirely hydrocarbon and that the molecular weight thereof be not more than 300.
• the especially preferred metal deactivator in the compositions of the invention is the compound N,N-disalicyiidene-1,2-propanediamine; however, another preferred compound is bis(l-acetonyl-ethylidene)-ethanediamine, which through keto-enol tautomerism contains the above group.
• the concentration of such metal deactivators in the compositions of the invention should *be at least one gram mol thereof per gram atom of metal in the metal salt conductivity additive. It is preferred that at least 5, and more especially at least gram mols of the meta] deactivator be present per gram atom of metal of the metal salt conductivity additive. Much higher concentrations of the metal deactivator can effectively be present without adversely affecting the conductivity benefits of the metal salt, even up to about 1000 or more gram mols of the metal deactivator per gram atom of metal in the conductivity additive. In general, however, economics and other considerations will dictate the use of no more than about 100, or preferably no more than about 80 gram mols of metal deactivator per gram atom of metal in the metal salt.
• the conductivity additive composition of the invention can advantageously contain sufficient mineral oil, such as kerosene, xylene, gasoline, naphtha, etc., to give the additive composition sufiicient fluidity for easy handling.
• a particularly preferred conductivity additive composition in accordance with the invention is one containing product E-2, i.e. chromium C -alkylsalicylate prepared as described in Example II above, and additionally, 450 parts by weight (for each part by weight chromium in the chromium material present) of the copolymer of Example XXt, and 50 gram mols of N,N'disalicylidene-l, Z-propanediamine per gram atom of chromium in the chromium material present.
• a particularly preferred hydrocarbon fuel composition in accordance with the invention is a jet fuel of the kerosene type containing a sufficient quantity of the additive composition of Example XXV that the concentration of chromium metal in the jet fuel is 0.03 part per million by weight.
• a conductivity composition consisting essentially of (1) a chromium alkyl salicylate having a molecular weight of 5002500 and (2) a copolymer of a vinyl pyridine and at least one ester of an acrylic acid and a long chain aliphatic alcohol containing at least 10 carbon atoms, the mol ratio of the vinyl pyridine to ester being from 1:15 to 2:1, said copolymer having an average molecular Weight between 5 10 to 25 10 the weight and 5000:1.
• the oil soluble nitrogen-containing copolymer is a copolymer of (1) a monovinyl-substituted pyridine of the group consisting of pyridines substituted on one of the ring carbon atoms with, as the sole substituted substituent, a vinyl group, and derivatives of the aforedescribed vinylpyridines having a lower alkyl group substituted on a ring carbon atom and (2) a mixture of a C to C alkyl ester of an acrylic acid of the group consisting of acrylic acid and methacrylic acid and a C to C alkyl ester of an acrylic acid of the group consisting of acrylic acid and methacrylic acid.
• a liquid hydrocarbon fuel composition consisting essentially of hydrocarbons boiling in the range of from -40 F. to 700 F. and a composition according to claim 1, in an amount suificient to provide said fuel composition with 1X10 to 1 10 gram atoms of chromium in the form of the salicylate per liter of hydrocarbon.
• liquid hydrocarbon fuel composition according to claim 3 containing in addition 1 10 to 1 10- mols per liter of a calcium dialkyl sulfosuccinate.
• the liquid hydrocarbon fuel composition according to claim 3 wherein the copolymer is one formed by copolymerization of 29.3% stearyl methacrylate, 49.7% lauryl methacrylate, 16% methyl methacrylate and 5.0% 2-methyl-5-vinyl pyridine.
• a conductivity additive composition consisting essentially of (1) a chromium alkylsalicylate having a molecular weight of from about 500 to about 2500 and (2) a copolymer of a vinylpyridine, a mixture of at least two dissimilar esters of an acrylic acid and long chain alcohols which mixture contains at least one pair of esters derived from alcohols differing by at least 4 carbon atoms and being present in a mol ratio to one another of from 1:10 to 10: 1, and at least one ester of an acrylic acid and a lower aikanol containing no more than 6 carbon atoms, in which copolymer the mol ratio of the vinylpyridine to the total esters is from 1:15 to 2:1 and the ester of the lower alkanol is from 10 to mol percent of the total esters, the weight ratio of copolymer to chromium being between 20:1 and 5000:1.

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• 0
  • NL NL251969D patent/NL251969A/xx unknown
  • NL NL120317D patent/NL120317C/xx active
• 1959
  • 1959-05-27 US US816039A patent/US3013868A/en not_active Expired - Lifetime
• 1960
  • 1960-05-25 DE DES68679A patent/DE1279267B/de active Pending
  • 1960-05-25 FR FR828239A patent/FR1269640A/fr not_active Expired
  • 1960-05-25 GB GB18466/60A patent/GB938118A/en not_active Expired
  • 1960-05-25 BE BE591230A patent/BE591230A/xx unknown

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