EP0518966B1 - Motorbrennstoffzusatzmittelzusammensetzung und methode zu ihrer herstellung - Google Patents

Motorbrennstoffzusatzmittelzusammensetzung und methode zu ihrer herstellung Download PDF

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EP0518966B1
EP0518966B1 EP91905918A EP91905918A EP0518966B1 EP 0518966 B1 EP0518966 B1 EP 0518966B1 EP 91905918 A EP91905918 A EP 91905918A EP 91905918 A EP91905918 A EP 91905918A EP 0518966 B1 EP0518966 B1 EP 0518966B1
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range
radical
additive
carbon atoms
fuel
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French (fr)
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EP0518966A4 (en
EP0518966A1 (de
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Alfred Richard Nelson
Mark L. Nelson
Otis L. Nelson, Jr.
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Polar Molecular Corp
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Polar Molecular Corp
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
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    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
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    • C10L1/1822—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
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    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1857—Aldehydes; Ketones
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    • C10L1/192—Macromolecular compounds
    • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
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    • C10L1/00—Liquid carbonaceous fuels
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    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
    • C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters
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    • C10L1/00—Liquid carbonaceous fuels
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    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
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    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
    • C10L1/2387—Polyoxyalkyleneamines (poly)oxyalkylene amines and derivatives thereof (substituted by a macromolecular group containing 30C)
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Definitions

  • This invention relates to a motor fuel additive composition and a method of preparing such an additive. More particularly, this invention relates to a motor fuel additive composition comprising: (a) a detergent component selected from the group consisting of, (i) a reaction product component which is the reaction product of a substituted hydrocarbon and an amino compound, and (ii) a polybutylamine or polyisobutylamine; and (b) a fuel conditioner component comprising (i) a polar oxygenated hydrocarbon compound, and (ii) an oxygenated compatibilizing agent.
  • This invention also relates to a method of preparing a motor fuel additive which comprises mixing the above-described reaction product and fuel conditioner components.
  • first generation additives directed primarily to cleaning carburetors and injectors include low molecular weight amine derivatives such as fatty amines, amides, amido amines and imidazolines.
  • second generation additives directed to cleaning inlet valves as well as carburetors and injectors, have been based primarily on polyolefinic structures, typically polyisobutenes and their derivatives.
  • Petroleum based oils useful in this respect include naphthenic and paraffinic base stock oils of relatively high viscosity, including so-called solvent Neutral Oils such as SNO-500 and SNO-600, as well as so-called top cylinder oils and the like.
  • Synthetic oils which have been employed include low molecular weight polypropylenes and polyisobutylenes, as well is polyalkyleneoxides.
  • a knocking engine does not effectively utilize the energy of combustion. Moreover, a prolonged period of engine knocking will cause stress fatigue and wear in vital parts of the engine.
  • the above-described phenomenon is characteristic of gasoline powered engines. It is usually overcome by employing a higher octane gasoline for powering the engine, and hence has become known as engine octane requirement increase (ORI) phenomenon.
  • an additive in motor fuel compositions which reduces deposits in engine fuel intake systems and also avoids the formation of deposits in engine combustion chambers, thereby reducing or at least modifying the composition of deposits which tend to cause engine ORI. It is an object of this invention to provide a motor fuel additive which is useful in preventing both fuel intake system deposit formation and combustion chamber deposit formation. It is a feature of this invention that the additive comprises a detergent component and a fuel conditioner component which synergistically interact to reduce both fuel intake system and combustion chamber deposit formation. It is an advantage of this invention that it both reduces deposit formation in engine fuel intake systems and ORI associated with combustion chamber deposit formation.
  • the motor fuel additive composition of this invention comprises a mixture of:
  • the fuel conditioner component may additionally comprise a hydrophilic separant such as a glycol monoether, and an aromatic hydrocarbon such as xylene or a xylene.
  • the additive composition may additionally comprise a carrier oil or fluidizer.
  • This invention is also directed to a method of preparing the motor fuel additive of this invention, which comprises mixing the detergent and fuel conditioner components to obtain the additive.
  • the motor fuel additive of this invention is advantageous in that the detergent and fuel conditioner components synergistically interact when employed in a fuel composition to reduce both fuel intake system deposit formation, thereby improving engine performance, and combustion chamber deposit formation, thereby reducing engine ORI.
  • Figure 1 depicts the results of engine test stand experiments for various motor fuel compositions, including motor fuel compositions containing the additive of this invention.
  • Figure 2 depicts the results of the engine test stand experiments set forth in Figure 1 for various motor fuel compositions, including motor fuel compositions containing the additive of this invention, as a plot of Combustion Chamber Rating vs. Intake Valve Deposits (mg).
  • This invention is directed to a motor fuel additive and to a method for the preparation thereof.
  • the additive comprises: (a) a detergent component which is selected from the group consisting of (i) the reaction product of a substituted hydrocarbon and an amino compound, (ii) a polybutylamine or polyisobutylamine; and (b) a fuel conditioner component comprising a polar oxygenated hydrocarbon compound and an oxygenated compatibilizing agent.
  • the substituted hydrocarbon reactant used to prepare the reaction product is of the formula R1 - X (I) wherein R1 is a hydrocarbyl radical having a molecular weight in the range of 150-10,000, preferably a polyalkylene radical having a molecular weight in the range of 400-5000, most preferably a polyalkylene radical having a molecular weight in the range of 600-1500, and X is selected from the group consisting of halogens, preferably chlorine, succinic anhydride and succinic dibasic acid.
  • R1-X is a polyisobutenyl succinic anhydride.
  • R1-X is a chloropolyisobutylene.
  • the amino compound reactant used to prepared the reaction product is of the formula H - (NH - (A) m ) n - Y - R2 (II) wherein Y is O or NR5, where R5 is H or a hydrocarbyl radical having 1-30, preferably 1-22 carbon atoms, A is a straight chain or branched chain alkylene radical having 1-30, preferably 1-15 carbon atoms, m has a value in the range of 1-15, preferably 1-12, n has a value in the range of 0-6, preferably 0-5, and R2 is selected from the group consisting of H, a hydrocarbyl radical having a molecular weight in the range of 15-10,000, preferably 15-2000, and a homopolymeric or heteropolymeric polyoxyalkylene radical of the formula R3 - ((Q) a (T) b (Z) c ) d - (III) wherein R3 is H or a hydrocarbyl radical having 1-30, preferably 1
  • R2 is the above-described homopolymeric or heteropolymeric polyoxyalkylene radical of formula (III).
  • homopolymeric and heteropolymeric refer to polyoxyalkylene compounds, which in the case of homopolymeric compounds contain one recurring polyoxyalkylene moiety, and in the case of heteropolymeric compounds contain more than one recurring polyoxyalkylene moiety, typically having 1-6 carbon atoms, such as ethylene oxide (EO), propylene oxide (PO) or butylene oxide (BO).
  • the above-described amino compound reactant is selected from the group consisting of polyethylene polyamines, polypropylene polyamines and mixtures thereof. In yet another preferred embodiment, such polyamines are monoalkylated.
  • the reaction product component is preferably prepared by reacting the substituted hydrocarbon R1-X to the amino compound in a mole ratio in the range of 0.2:1 - 20:1, more preferably in the range of 0.5:1 - 10:1.
  • the reaction product component may be prepared under reaction conditions (including e.g. reaction times, temperatures, and reagent proportions) as are well known by those skilled in the art for preparing such amino compound-substituted hydrocarbon reaction products.
  • the method for preparing such reaction products is described, for example, in U.S. Pat. No. 3,172,892 (LeSeur et al.), U.S. Pat. No. 3,438,757 (Honnen et al.), and U.S. Pat. No. 3,443,918 (Kautsky et al.).
  • the detergent compound may also be a polybutylamine or polyisobutylamine of the formula where R11 is a polybutyl- or polyisobutyl radical derived from isobutene and up to 20% by weight of n-butene, and R12 and R13 are identical or different and are each hydrogen, an aliphatic or aromatic hydrocarbon, a primary or secondary, aromatic or aliphatic aminoalkylene radical or polyaminoalkylene radical, a polyoxyalkylene radical or a hetaryl or heterocyclyl radical, or, together with the nitrogen atom to which they are bonded, form a ring in which further hetero atoms may be present.
  • R11 is a polybutyl- or polyisobutyl radical derived from isobutene and up to 20% by weight of n-butene
  • R12 and R13 are identical or different and are each hydrogen, an aliphatic or aromatic hydrocarbon, a primary or secondary, aromatic or aliphatic aminoalkylene
  • the fuel conditioner component employed in admixture with the detergent component to produce the additive of this invention may preferably be the fuel conditioner previously disclosed in U.S. Pat. No. 4,753,661 (Nelson et al.).
  • This fuel conditioner comprises a polar oxygenated hydrocarbon compound and an oxygenated compatibilizing agent.
  • the polar oxygenated hydrocarbon portion of the fuel conditioner signifies various organic mixtures arising from the controlled oxidation of petroleum liquids with air. Often these air oxidations of liquid distillates are carried out at a temperature of from about 100°C to about 150°C with an organometallic catalyst, such as esters of manganese, copper, iron, cobalt, nickel or tin, or organic catalysts, such as tertiary butyl peroxide.
  • organometallic catalyst such as esters of manganese, copper, iron, cobalt, nickel or tin
  • organic catalysts such as tertiary butyl peroxide.
  • the result is a melange of polar oxygenated compounds which may be divided into at least three categories: volatile, saponifiable and non-saponifiable.
  • the polar oxygenated compounds preferable for use in the present invention may be characterized in a least three ways, by molecular weight, acid number, and saponification number. Chemically these oxidation products are mixtures of acids, hydroxy acids, lactones, esters, ketones, alcohols, anhydrides, and other oxygenated organic compounds. Those suitable for the present invention are compounds and mixtures with an average molecular weight between about 250 and 500, with an acid number between about 25 and about 175 (ASTM-D-974), and a saponification number from about 30 to about 250 (ASTM-D-974-52).
  • the polar oxygenated compounds of the present invention have an acid number from about 50 to about 100 and a saponification number from about 75 to about 200.
  • An example of a polar oxygenated hydrocarbon within this preferred range is ALOX 400L (Alox Corporation, Niagara Falls, New York).
  • Suitable compatibilizing agents for use in the fuel conditioner component of the instant invention are organic compounds of moderate solubility parameter and moderate to strong hydrogen-bonding capacity.
  • Solubility parameters, ⁇ , based on cohesive energy density are a fundamental descriptor of an organic solvent giving a measure of its polarity. Simple aliphatic molecules of low polarity have a low ⁇ of about 7.3; highly polar water has a high ⁇ of 23.4. Solubility parameters, however, are just a first approximation to the polarity of an organic solvent. Also important to generalized polarity, and hence solvent power, are dipole moment and hydrogen-bonding capacity.
  • a compatibilizing agent should have a solubility parameter from about 8.8 to about 11.5 and moderate to strong hydrogen-bonding capacity.
  • Suitable classes of organic solvents are alcohols, ketones, esters, and ethers.
  • Preferred compatibilizing agents are straight-chain, branched-chain, and alicyclic alcohols with from six to 14 carbon atoms.
  • Especially preferred compounds for compatibilizing agents are the hexanols, the heptanols, the octanols, the nonyl alcohols, the decanols, and the dodecanols.
  • the fuel conditioner component of this invention may additionally include a hydrophilic separant which decreases the amount of water in the hydrocarbon fuel, thus improving combustion.
  • Suitable separants for practicing the current invention are ethers of glycols or polyglycols, especially monoethers. Monoethers are preferred over diethers in the practice of the present invention.
  • Examples of such compounds which may be used are the monoethers of ethylene glycol, propylene glycol, trimethylene glycol, alphabutylene glycol, 1,3-butanediol, beta-butylene glycol, isobutylene glycol, tetramethylene glycol, hexylene glycol, diethylene glycol, dipropylene glycol, tripropylene glycol, triethylene glycol, tetraethylene glycol, 1,5-pentanediol, 2-methyl-2-ethyl-1,3-propanediol, 2-ethyl-1,3-hexanediol.
  • Some monoethers include ethylene glycol monophenyl ether, ethylene glycol monomethylether, ethylene glycol monoethyl ether, ethylene glycol mono-(n-butyl) ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-(n-butyl) ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, diethylene glycol monocyclohexylether, ethylene glycol monobenzyl ether, triethylene glycol monophenethyl ether, butylene glycol mono-(p-(n-butoxy) phenyl) ether, trimethylene glycol mono(alkylphenyl) ether, tripropylene glycol monomethyl ether, ethylene glycol mono-isopropyl ether, ethylene glycol monoisobutyl ether, ethylene glycol monohexyl ether, triethylene glycol monobutyl ether, triethylene glycol m
  • Such compounds are sold commercially under trade names such as Butyl CELLOSOLVE, Ethyl CELLOSOLVE, Hexyl CELLOSOLVE, Methyl CARBITOL, Butyl CARBITOL, DOWANOL Glycol ethers, and the like.
  • an aromatic hydrocarbon or a mixture of such, in the fuel conditioner component of the present invention.
  • Any aromatic hydrocarbon blend that is liquid at room temperature is suitable.
  • the preferred aromatic constituent is a commercial mixture of the three xylenes, because it is cheaper than any pure xylene.
  • xylene means not only the three specific xylene compounds o-xylene, m-xylene and p-xylene, but also includes aromatic "cuts” or distillates of aromatic hydrocarbons containing not only xylene but benzene, toluene, durene and naphthalene which may be mixed in the xylene. Aromatic naphthas are also useful. Without being limited to any theory or hypotheses for the use of an aromatic hydrocarbon, it has been found that the presence of an aromatic hydrocarbon in the conditioner promotes clean and efficient combustion of the fuel.
  • composition of this invention may additionally comprise a suitable amount of a carrier oil or fluidizer selected from the group consisting of petroleum-based oils, mineral oils, polypropylene compounds having a molecular weight in the range of 500-3000, polyisobutylene compounds having a molecular weight in the range of 500-3000, polyoxyalkylene compounds having a molecular weight in the range of 500-3000, and polybutyl and polyisobutyl alcohols containing polybutyl or polyisobutyl radicals derived from polyisobutene and up to 20% by weight of n-butene, corresponding carboxylates of the polybutyl or polyisobutyl alcohol, and mixtures thereof.
  • a carrier oil or fluidizer selected from the group consisting of petroleum-based oils, mineral oils, polypropylene compounds having a molecular weight in the range of 500-3000, polyisobutylene compounds having a molecular weight in the range of 500-3000, polyoxyalkylene compounds having a molecular weight
  • Petroleum based oils which may be employed include top cylinder oils as well as both natural and synthetic napthenic and paraffinic base stock oils of relatively high viscosity, including so-called Solvent Neutral Oils (SNO) such as SNO-500 and SNO-600.
  • Mineral oils which may be employed include so-called "light” mineral oils, i.e. those petroleum, aliphatic or alicyclic fractions having a viscosity less than 10,000 SUS at 25°C. A mixture of hydrocarbon fractions may also be employed in place of a base stock.
  • the above-described polybutyl and polyisobutyl alcohols include those disclosed in U.S. Pat. No; 4,859,210 (Franz et al.).
  • carrier oil and “fluidizer” are interchangeable, as will be readily understood by those skilled in the art.
  • the additive composition of this invention may be employed in a wide variety of hydrocarbon or modified hydrocarbon (e.g. alcohol-containing) fuels for a variety of engines.
  • Preferred motor fuel compositions for use with the additive composition of this invention are those intended for use in spark ignition internal combustion engines.
  • Such motor fuel compositions generally referred to as gasoline base stocks, preferably comprise a mixture of hydrocarbons boiling in the gasoline boiling range, preferably from about 90-450°F.
  • This base fuel may consist of straight chains, branch chains, paraffins, cycloparaffins, olefins, aromatic hydrocarbons, and mixtures thereof.
  • the base fuel may be derived from, among others, straight run naptha, polymer gasoline, natural gasoline, or from catalytically cracked or thermally cracked hydrocarbons and catalytically reformed stock.
  • the fuel may also contain synthetic hydrocarbons, ethers such as methyl tertiary butyl ether (MTBE), ethyl tertiary butyl ether (ETBE) and the like, alcohols such as methanol, ethanol, TBA and the like, and other functional organic compounds such as ketones, esters and the like.
  • MTBE methyl tertiary butyl ether
  • ETBE ethyl tertiary butyl ether
  • alcohols such as methanol, ethanol, TBA and the like
  • other functional organic compounds such as ketones, esters and the like.
  • the composition and octane level of the base fuel are not critical and any conventional motor base fuel may be employed in the practice of this invention.
  • the motor fuel composition may additionally comprise other additives typically employed in motor fuels, such as anti-knock compounds (e.g. tetraethyl lead), anti-icing additives, upper cylinder lubricating oils, carburetor detergents, anti-corrosion additives, de-emulsifying agents, odor suppressors, and the like.
  • Example 2 The identical test performed in Example 1 was repeated except that each vehicle used an unleaded base fuel containing a different commercially available fuel detergent additive package at its recommended level. After 7000 miles, the following results were obtained:
  • Example 1 The identical test performed in Example 1 was run, except that each vehicle used an unleaded base fuel containing 500 ppm of the fuel conditioner component of this invention, as disclosed in U.S. Pat. No. 4,753,661 and available from Polar Molecular Corp. (Saginaw, Mi.) under the DurAlt Fuel Conditioner trade name.* The following results were obtained: * Contained 30% (by weight of fuel conditioner) active polar oxygenated compound.
  • Example 1 The identical test performed in Example 1 was run, except that each vehicle used an unleaded base fuel containing its respective additive (A or B) as in Example 2 plus 500 ppm of the fuel conditioner component of this invention available from Polar Molecular Corp. (Saginaw, Mi.) under the DurAlt Fuel Conditioner trade name. The following results were obtained: Car #1 Car #2 Additive Type A+500ppm DurAlt B+500ppm DurAlt Inlet Valve deposits (g) 0.35 ⁇ 0.1 Combustion Chamber deposits (g) 0.45 0.4
  • Example 1 The identical test performed in Example 1 was run, except that each vehicle used an unleaded base fuel containing its respective additive (A or B) as in Example 2 plus 300 pm and 100 ppm, respectively, of the DurAlt fuel conditioner.
  • a or B additive
  • Example 1 The identical test performed in Example 1 was run for Car #2, except that Car #2 used an unleaded base fuel having additive package B plus 500 ppm of a commercial fuel additive as disclosed in U.S. Patent No. 4,548,616 (Sung et al.), the additive being a poly (oxyethylene)(oxypropylene) polyol.
  • a commercial fuel additive as disclosed in U.S. Patent No. 4,548,616 (Sung et al.), the additive being a poly (oxyethylene)(oxypropylene) polyol.
  • Such additives are available from BASF Wyandotte Corp. under the PLURONIC series trade name.
  • This vehicle was then con for 2000 miles on a fuel containing an additive composition of this invention, namely an additive composition comprising additive B as set forth in Example 2 (i.e. 350 ppm polybutene amino type additive and 600 ppm top cylinder oil) + 500 ppm of DurAlt FC.
  • the knocking problems totally disappeared, thus showing a clear reduction in engine ORI for this vehicle.
  • This example illustrates the utility of this invention in so-called "clean-up" applications, wherein use of the invention improves performance of engines which have already demonstrated engine ORI.
  • the engine was prepared for testing by first being disassembled.
  • the intake valves ware then cleaned with gum solvent consisting of a mixture of 1/3 acetone, 1/3 toluene, and 1/3 methanol to remove any lube oil on the valves.
  • the valves were then stored in a desiccator for at least one hour, and thereafter weighed to the nearest 0.1 mg, just prior to engine assembly.
  • the combustion chambers and ports were cleaned with a suitable wire brush, as were the tops of the pistons.
  • the clean cylinder heads were reassembled and installed onto the engine, and the remainder of the engine was reassembled.
  • the oil and oil filter were replaced prior to testing.
  • the fuel composition to be tested was prepared and poured into the fuel tank.
  • the engine was started and allowed to idle for 30 second to warm up.
  • the engine was then allowed to run under a 1500 watt load for two hours.
  • the generator load, coolant in/out temperature, oil temperatures exhaust temperature for cylinders 1 and 2, and manifold vacuum were recorded.
  • the engine was then run for an additional two hour period under a 2500 watt load.
  • the above-described data were again recorded.
  • the above-described four hour test run procedure was repeated (with intervening refueling) for 16 hours of engine running per day, for five consecutive, days for a total of 80 hours of engine running.
  • the generator fuel tank was drained and added to the remaining fuel mix for the run. The total volume of fuel remaining was measured to calculate the amount of fuel used during the 80 hour run.
  • the engine was disassembled, including removal of the cylinder head, cam shaft, and rocker arm assembly.
  • the amount of deposits on the intake system consisting of the carburetor throttle plate, intake manifold, head runners, head ports, and intake valves were rated using the method described by Coordinating Research Council (CRC) Rating Manual No. 16, Atlanta, Ga. 1987 (“CRC Rating"), which is well known to those skilled in the art.
  • CRC Rating Coordinating Research Council
  • the combustion chamber and piston tops were similarly rated using the CRC Rating system.
  • the sequence for rating, valve weighing, and photographing was as follows: the piston tops, cylinder head, combustion chamber, head runners, intake manifold, and throttle plate were all initially rated, and photographed.
  • the combustion side of the intake valves were thereafter cleaned, and the intake valves were removed carefully so as to not disturb any deposits residing thereon.
  • the valve stems were wiped with gum solvent to remove lube oil, and thereafter photographed.
  • the valves were then placed in a desiccator for one hour and then removed and immediately weighed, with the weight being recorded to the nearest 0.1 mg.
  • the valves were then put back into the desiccator for an additional 0.5 hour and reweighted, this process was repeated until valve weighings were within 0.5 mg.
  • the valve was then cleaned with gum solvent and wire brush, and stored in a desiccator until ready for final weighing.
  • the engine was thereafter reassembled with a new set of intake valves, and the engine runs were repeated.
  • a base fuel composition obtained from the Sun Refining and Marketing Company was used in all of the following examples.
  • the analysis of the base fuel composition was as follows: Item Result API Gravity, ASTM D287 56.1 Research Octane No., ASTM D2699 95.2 Motor Octane, ASTM D2700 84.2 Sensitivity, (R-M) 11.0 Octane, (R+M)/2 89.7 Reid Vapor Pressure, psi ASTM D323 Automated 9.1 Distillation, ASTM D86 Automated IBP 93 10% Evap. 131 50% Evap. 220 90% Evap. 336 FBP 411 Hydrocarbon Composition, Vol. %, ASTM D1319 Aromatics 30.4 Olefins 17.1 Saturates 52.5
  • Fuel No. Detergent Component 250 mg/l fuel
  • Fuel Conditioner** Component Carrier Oil* (250 mg) I (comparative) __ yes yes II (comparative) polyisobutylamine __ yes III (invention) polyisobutylamine yes yes IV (comparative) polybutylamine __ yes V (invention) polybutylamine yes yes VI (comparative) isooctylphenyl polyethoxy ethanol __ yes VII (invention) isooctylphenyl polyethoxy ethanol yes yes *
  • carrier oil used was 250 mg of 1:1 blend of SN0-600 oil and synthetic oil.
  • Fuel conditioner component was 100mg/l fuel polar oxygenated hydrocarbon plus 40ppm compatibilizer (hexanol).
  • Fuels Nos. I-VII were rated in terms of the amount of intake valve deposits (in mg) and for combustion chamber (CRC) rating, as summarized in Figure 1.
  • Figure 2 which plots the data set forth in Figure 1, Fuel Nos. III, V, and VII (i.e. the fuel compositions comprising the additive of this invention) exhibited superior properties both in terms of combustion chamber rating (i.e. high CRC rating) and reduction of intake valve deposits (i.e. low value of mg of deposits on intake valves).

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Claims (18)

  1. Additiv für Motortreibstoff, das eine Mischung enthält aus:
    (a) 5-50 Gew.-%, bezogen auf das Gesamtgewicht des Additivs eines Detergenz, ausgewählt aus der Gruppe bestehend aus:
    (i) einem Reaktionsprodukt von:
    (A) einem substituierten Kohlenwasserstoff der Formel



            R₁ - X   (I)



    wobei R₁ ein Kohlenwasserstoffrest ist, der ein Molekulargewicht in dem Bereich zwischen 150-10,000 hat, und X aus der Gruppe bestehend aus Halogenen, Bernsteinsäureanhydrid und zweibasischer Bernsteinsäure ausgewählt ist, und
    (B) einem Amin der Formel



            H - (NH - (A)m)n - Y - R₂   (II)



    in der Y gleich O oder NR₅ und R₅ H oder ein Kohlenwasserstoffrest mit 1-30 Kohlenstoffatomen ist; A ein gradkettiger oder verzweigter Alkylenrest mit 1-30 Kohlenstoffatomen ist; m einen Wert im Bereich von 1-15 hat; n einen Wert im Bereich von 0-6 hat; und R₂ ausgewählt ist aus der Gruppe bestehend aus H, einem Kohlenwasserstoffrest mit einem Molekulargewicht im Bereich von 15-10,000, und einem homopolymeren oder heteropolymeren Polyoxyalkylenrest der Formel



            R₃ - ((Q)a(T)b(Z)c)d -   (III)



    wobei R₃ H oder ein Kohlenwasserstoffrest mit 1-30 Kohlenstoffatomen ist, Q, T und Z Polyoxyalkylenreste mit 1-6 Kohlenstoffatomen sind, a, b und c jeweils Werte zwischen 0 und 30 aufweisen und d einen Wert im Bereich zwischen 1 und 50 hat, und
    (ii) einem Polybutylamin oder Polyisobutylamin der Formel
    Figure imgb0007
     in der R₁₁ ein Polybutyl- oder Polyisobutylrest ist, der abgeleitet ist vom Isobuten und bis zu 20 Gew.-% n-Buten, und R₁₂ und R₁₃ gleich oder verschieden sind und jeweils Wasserstoff, einen aliphatischen oder aromatischen Kohlenwasserstoffrest, einen primären oder sekundären, aromatischen oder aliphatischen Aminoalkylen- oder Polyaminoalkylenrest, einen Polyoxyalkylen, einen Heteroaryl- oder Heterocyclylrest, oder zusammen mit dem Stickstoffatom, an das sie gebunden sind, einen Ring bilden, in dem weitere Heteroatome vorhanden sein können; und
    (b) eine den Treibstoff konditionierende Verbindung enthaltend:
    (i) 2-50 Gew.-%, bezogen auf das Gesamtgewicht des Additivs, eines polaren, sauerstoffhaltigen Kohlenwasserstoffes mit einem durchschnittlichen Molekulargewicht im Bereich zwischen 250-500, einer Säurezahl im Bereich zwischen 25-175, und einer Verseifungszahl im Bereich von etwa 30-250 und
    (ii) 2-50 Gew.-%, bezogen auf das Gesamtgewicht des Additivs, einersauerstoffhaltigen, kompatibilisierend wirkenden Verbindung, die einen Löslichkeitsparameter im Bereich von etwa 8,8-11,5 und eine mäßige bis starke Fähigkeit zur Wasserstoffbindung aufweist.
  2. Additiv gemäß Anspruch 1, in dem das molare Verhältnis des substituierten Kohenwasserstoffs R₁-X zum Amin in dem Bereich zwischen 0,2:1 bis 20:1 liegt.
  3. Additiv gemäß Anspruch 1, bei dem R₁-X ein Chlorpolyisobutylen oder ein Polyisobutylen-Bernsteinsäureanhydrid ist.
  4. Additiv gemäß Anspruch 1, in dem R₂ ausgewählt ist aus der Gruppe bestehend aus Wasserstoff, einem Kohlenwasserstoffrest mit einem Molekulargewicht im Bereich von 15-2000, und einem Polyoxyalkylenrest der Formel (III), in der R₃ H oder ein Kohlenwasserstoffrest ist mit 1-22 Kohlenstoffatomen, Q, T und Z Polyoxyalkylenhälften mit 1-6 Kohlenstoffatomen sind, a, b, c und d Werte im Bereich von 1-25 haben, Y gleich O oder NR₅ ist, wobei R₅ H oder ein Kohlenwasserstoffrest mit 1-22 Kohlenstoffatomen ist, A ein geradkettiger oder verzweigter Alkylenrest mit 1-15 Kohlenstoffatomen ist, m einen Wert im Bereich zwischen 1-12 und n einen Wert im Bereich zwischen 0 und 5 aufweist.
  5. Additiv nach Anspruch 1, bei dem das Amin der Formel (II) aus der Gruppe bestehend aus Polyäthylenpolyaminen, Polypropylenpolyaminen und ihren Mischungen ausgewählt ist.
  6. Additiv gemäß Anspruch 1, bei dem die kompatibilisierende Verbindung ein Alkohol ist, der drei oder mehr Kohlentoffatome enthält.
  7. Additiv gemäß Anspruch 1, bei dem die den Treibstoff konditionierende Verbindung zusätzlich 0-40 Gew.-%, bezogen auf das Gesamtgewicht des Additivs, eines hydrophilen Abtrennmittels enthält.
  8. Additiv gemäß Anspruch 1, bei dem die den Treibstoff konditionierende Verbindung zusätzlich 0-80 Gew.-%, bezogen auf das Gesamtgewicht des Additivs, eines aromatischen Kohlenwasserstoffs enthält.
  9. Additiv gemäß Anspruch 1, das zusätzlich 0-80 Gew.-%, bezogen auf das Gesamtgewicht des Additivs eines Trägeröls ausgewählt aus der Gruppe der aus Petroleum gewonnenen Öle, Mineralöle, Polypropylen-Verbindungen mit einem Molekulargewicht im Bereich zwischen 500 und 3000, PolyisobutylenVerbindungen mit einem Molekulargewicht im Bereich von 500-3000, Polyoxyalkylen-Verbindungen mit einem Molekulargewicht im Bereich von 500-3000, und Polybutyl- und Polyisobutylalkohole, die Polybutyl- oder Polyisobutylreste enthalten, die sich vom Polyisobuten und bis zu 20 Gew.-% n-Buten ableiten, sowie entsprechende Carboxylate des Polybutyl- oder Isobutyl-Alkohols und deren Mischungen.
  10. Verfahren zur Herstellung einer Additivverbindung für Motortreibstoffe, bei welchem man mischt:
    (a) 5-50 Gew.-%, bezogen auf das Gesamtgewicht des Additivs, eines Detergenz, ausgewählt aus der Gruppe bestehend aus:
    (i) dem Reaktionsprodukt von:
    (A) einem substituierten Kohlenwasserstoff der Formel



            R₁ - X   (I)



    in der R₁ ein Kohlenwasserstoffrest mit einem Molekulargewicht im Bereich zwischen 150 und 10,000 und X aus der Gruppe bestehend aus Halogenen, Bernsteinsäureanhydrid und zweibasischer Bernsteinsäure ausgewählt ist, und
    (B) einem Amin der Formel



            H - (NH - (A)m)n - Y - R₂   (II)



    in der Y O oder NR₅ ist, wobei R₅ H oder ein Kohlenwasserstoffrest mit 1-30 Kohlenstoffatomen ist; A ein geradkettiger oder verzweigter Alkylenrest mit 1-30 Kohlenstoffatomen ist; m einen Wert im Bereich zwischen 1-15 hat; n einen Wert im Bereich zwischen 0-6 hat; und R₂ ausgewählt ist aus der Gruppe bestehend aus Wasserstoff, einem Kohlenwasserstoffradikal mit einem Molekulargewicht im Bereich von 15-10,000 und einem homopolymeren oder heteropolymeren Polyoxyalkylenrest der Formel



            R₃ - ((Q)a(T)b(Z)c)d -   (III)



    ist, in der R₃ H oder ein Kohlenwasserstoffrest mit 1-30 Kohlenstoffatomen, Q, T und Z Polyoxyalkylenreste mit 1-6 Kohlenstoffatomen, a, b und c jeweils Werte zwischen 0-30 und d einen Wert zwischen 1-50 aufweisen und
    (ii) einem Polybutylamin oder Polyisobutylamin der Formel
    Figure imgb0008
     in der R₁₁ ein Polybutyl- oder Polyisobutylrest ist, der sich von Isobuten und bis zu 20 Gew.-% n-Buten ableitet und R₁₂ und R₁₃ gleich oder verschieden und jeweils Wasserstoff, ein aliphatischer oder aromatischer Kohlenwasserstoff, ein primärer oder sekundärer, aromatischer oder aliphatischer Aminoalkylenrest oder Polyaminoalkylenrest, ein Polyoxyalkylenrest oder ein Heteroaryl- oder Heterocyclylrest sind, oder zusammen mit dem Stickstoffatom, an das sie gebunden sind, einen Ring bilden, in dem weitere Heteroatome vorhanden sein können; und
    (b) eine den Treibstoff konditionierende Verbindung enthaltend:
    (i) 2-50 Gew.-%, bezogen auf das Gesamtgewicht des Additivs, eines polaren, sauerstoffhaltigen Kohlenwasserstoffes mit einem durchschnittlichen Molekulargewicht im Bereich von 250-500, einer Säurezahl im Bereich zwischen 25-175 und einer Verseifungszahl im Bereich von etwa 30-250 und
    (ii) 2-50 Gew.-%, bezogen auf das Gesamtgewicht des Additivs, einersauerstoffhaltigen, kompatibilisierend wirkenden Verbindung mit einem Löslichkeitsparameter im Bereich von etwa 8,8-11,5 und mäßiger bis starker Fähigkeit zur Bindung von Wasserstoff.
  11. Verfahren nach Anspruch 10, in dem das molare Verhältnis des substituierten Kohlenwasserstoffes R₁-X zum Amin im Bereich zwischen 0,2:1 bis 20:1 liegt.
  12. Verfahren gemäß Anspruch 10, in dem R₁-X ein Chlorpolyisobutylen oder ein Polyisobuten-Bernsteinsäureanhydrid ist.
  13. Verfahren nach Anspruch 10, in dem R₂ ausgewählt ist aus der Gruppe bestehend aus H, einem Kohlenwasserstoffrest mit einem Molekulargewicht im Bereich zwischen 15-2000, und einem Polyoxyalkylenrest der Formel (III), in der R₃ H oder ein Kohlenwasserstoffrest mit 1-22 Kohlenstoffatomen, Q, T und Z Polyoxyalkylenreste mit 1-6 Kohlenstoffatomen, a, b, c und d Werte zwischen 1-25, Y O oder NR₅ bedeutet, wobei R₅ H oder ein Kohlenwasserstoffrest mit 1-22 Kohlenstoffatomen ist, A ein geradkettiger oder verzweigter Alkylenrest mit 1-15 Kohlenstoffatomen ist, m einen Wert zwischen 1-12 und n einen Wert zwischen 0-5 hat.
  14. Verfahren nach Anspruch 10, in dem das Amin der Formel (II) ausgewählt ist aus der Gruppe bestehend aus Polyäthylenpolyaminen, Polypropylenpolyaminen und deren Mischungen.
  15. Verfahren nach Anspruch 10, in dem die kompatibilisierend wirkende Verbindung ein Alkohol mit drei oder mehr Kohlenstoffatomen ist.
  16. Verfahren nach Anspruch 10, in dem die den Treibstoff konditionierende Verbindung zusätzlich 0-40 Gew.-%, bezogen auf das Gesamtgewicht des Additivs, eines hydrophilen Abtrennmittels enthält.
  17. Verfahren nach Anspruch 10, in dem die den Treibstoff konditionierende Verbindung zusätzlich 0-80 Gew.-%, bezogen auf das Gesamtgewicht des Additivs, eines aromatischen Kohlenwasserstoffes enthält.
  18. Verfahren nach Anspruch 10, bei dem zusätzlich das Reaktionsprodukt und die den Treibstoff konditionierende Verbindungen mit 0-80 Gew.-%, bezogen auf das Gesamtgewicht des Additivs, eines Trägeröls zugemischt werden, das ausgewählt ist aus der Gruppe bestehend aus sich vom Petroleum ableitenden Ölen, Mineralölen, Polypropylen-Verbindungen mit einem Molekulargewicht im Bereich zwischen 500-3000, Polyisobutylen-Verbindungen mit einem Molekulargewicht im Bereich zwischen 500-3000, Polyoxyalkylen-Verbindungen mit einem Molekulargewicht im Bereich zwischen 500-3000, und Polybutyl- und Polyisobutylalkoholen, die Polybutyl- oder Polyisobutylreste enthalten, die vom Polyisobuten und bis zu 20 Gew.-% vom n-Buten abgeleitet sind, entsprechende Carboxylate des Polybutyl- oder Polyisobutylalkohols und deren Mischungen.
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DK0518966T3 (da) 1996-01-29
KR920703766A (ko) 1992-12-18
AU7484691A (en) 1991-10-10
EP0518966A4 (en) 1993-03-10
EP0518966A1 (de) 1992-12-23
JP2966927B2 (ja) 1999-10-25
JPH05505209A (ja) 1993-08-05
CA2077666A1 (en) 1991-09-06
ES2081472T3 (es) 1996-03-16
AU660608B2 (en) 1995-07-06
DE69115894D1 (de) 1996-02-08
GR3019268T3 (en) 1996-06-30
ATE132180T1 (de) 1996-01-15
KR0151409B1 (ko) 1998-10-01
DE69115894T2 (de) 1996-05-30
CA2077666C (en) 2004-06-22
WO1991013949A1 (en) 1991-09-19
BR9106137A (pt) 1993-03-02

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