Classifications

• • 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
  • C10L10/00—Use of additives to fuels or fires for particular purposes
  • C10L10/10—Use of additives to fuels or fires for particular purposes for improving the octane number
• • 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
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/234—Macromolecular compounds
  • C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
• • 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
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/234—Macromolecular compounds
  • C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
  • C10L1/2364—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amide and/or imide groups
• • 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
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/234—Macromolecular compounds
  • C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
  • C10L1/2366—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amine groups
• • 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
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/234—Macromolecular compounds
  • C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
  • C10L1/2368—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing heterocyclic compounds containing nitrogen in the ring

Definitions

• This invention relates to improved hydrocarbon compositions boiling substantially within the gasoline boiling range, particularly such compositions designed to be used as fuels in internal combustion engines.
• Another fuel system mechanism which is particularly prone to malfunctioning due to plugging with ice is the carburetor. moisture is introduced from the air for combustion. Even though both liquid fuel and air temperatures are above 32 F., the evaporation of the fuel in the carburetor'will often cool the system to 32 F. or-below, especially soon after starting the engine, whereupon ice will form and will frequently cause the engine to stall because of the blocking of fuel and air passages by the ice.
• these ditficultie's have sometimes been alleviated by incorporating into the hydrocarbon product certain water-soluble freezing point depressants, such as alcohols, including glycols, or the like.
• freezing point depressants such as alcohols, including glycols, or the like.
• these large concentrations are not only uneconomical but also often adversely aifect the chemical and physical properties of the product.
• the high water solubility of these com- .pounds makes them susceptible to removal from the hydrocarbon product by the leaching action of the free At this pointinthe fuel system, additional water with which the product usually comes in" contact Patented May 2,1961
• A" more particular object is to provide such a'composition which has im-' proved characteristics with respect to ice formation there-- in.
• a further object of the invention is to provide a gasoline fuel composition with improved anti-icing characteristics.
• Still further an object of the invention is to provide a hydrocarbon composition with improved characteristics with respect to ice formation therein and which requires neither a water soluble anti-icing additive nor a hLgh concentration of an anti-icing additive.
• the polymeric additive alleviates icing difficulties is not known. Since the additive is not water soluble, it probably does not act strictly as a freezing point depressant, and so it may'not actually prevent the formation of ice when the hydrocarbon prod:
• the hydrocarbon base, material which is the major component of the composition of the invention can be any hydrocarbon or mixture of hydrocarbons boiling substantially within the gasoline boiling range, that is, those with normal boiling points from about 30 F. to about 450 F.
• the invention is"'particularly directed to mixtures of hydrocarbons within an ASTM boiling range of about 350 F. s v I
• the polymeric additive of the invention is an oilsoluble polymeric amine having a molecular weightsuch I that its inherent viscosity at 0.1% concentration in ben zene at 25 C .'is at least 0.1 and preferably no greater i than 3.0, containing from about 0.2 to about S%'by" weight of amino nitrogen and having a carbon to amine i nitrogen ratio'of at least 2O to 1'.
• polymerizable esters, amides, and bydrocarbons characterized by the presence of at least eight carbon atoms, preferably with six or more in a straight hydrocarbon chain, with one terminal carbon to carbon double bond.
• Examples of such compounds are the saturated and unsaturated long chain esters of unsaturated carboxylic acids, preferably alpha-beta-unsaturated acids, such as decyl acrylate, 3,5,5-trimethylhexyl acrylate, 9- octadecenyl methacrylate; vinyl esters of long chain carboxylic acids, such as vinyl laurate, vinyl stearate; N-long chain hydrocarbon substituted amides of unsaturated acids such as N-octadecyl acrylamide; long chain unsaturated monoolefins such as the alkylstyrenes, e.g., dodecylstyrene; and the like.
• the oleophilic component is an acrylic acid ester, and in particular, technical lauryl methacrylate.
• amino nitrogen component there can be employed amino-substituted olefins such as p-(beta-die-thylaminoethyl)styrene; polymerizable amino nitrogen-concontaining heterocycles, e.g., vinylpyridine and the vinyl alkyl pyridines such as 2-vinyl-5-ethylpyridine; vinyl ethers of amino alcohols, such as beta-diethylaminoethyl vinyl ether; amides of unsaturated carboxylic acids having amino substituents on the amido nitrogen, such as N-(beta-dimethylaminoethyl)acrylamide; polymerizable unsaturated amines, such as diallylamine, and as a preferred class, an amino nitrogen-containing ester of an acrylic acid, especially and most usefully acrylic and methacrylic acid esters of N-beta-hydroxyethyl tertiary amines.
• amino-substituted olefins
• the ratio of the monomers of the copolymer can vary widely. It is preferred, however, that the ratio of the oleophilic monomer to the nitrogen monomer be at least 1:1 and preferably at least 3:2. On the other hand, this ratio should not be greater than about 50:1 and preferably not greater than 25:1. Especially useful copolymers are those wherein this ratio is from about 3:1 to about 20:1.
• An especially preferred polymeric amine is a copolymer of lauryl methacrylate and betadiethylaminoethylmethacrylate in which these monomers are respectively present in a ratio of from about 80:20 to about 95:5.
• R is a hydrogen or a lower ,alkyl group such as methyl or ethyl
• O is an oleophilic group preferably saturated such as an alkyl group or alkaryl group, containing a straight chain hydrocarbyl group of at least 6 carbon atoms and preferably 12 to 20 carbon atoms, for example, lauryl, octadecyl, hexadecyl, 2- or 4-octylphenyl or the like
• B is a basic nitrogen group, especially an amino-nitrogen group such as a di-lower-alkylaminoalkyl group, or a di-lower-alkylaminoalkaryl group, or a substituted or unsubstituted pyridyl group, for example, beta-diethylaminoethyl, dimethylaminomethyl 4 phenyl, or Z-methyl 4 pyr
• the effective concentrations of the copolymers in the hydrocarbon compositions of the invention are extremely small, being generally less than 100 parts per million (wt.).
• the concentration can be as low as 0.1 part per million in some cases, although it is preferred that at least 1 and especially at least 5 parts per million be used. Also preferred are concentrations no greater than 50 parts per million and usually no greater than 30 parts per million. For best results, especially in aviation gasoline, concentrations no greater than 10 parts per million should be used.
• the hydrocarbon compositions of the invention can, and ordinarily will, contain other additives, such as the common commercial additives, for example, anti-detonants such as tetraethyl lead, iron carbonyl, dicyclopeutadienyl iron, xylidene, and N-methyl aniline, lead scavengers such as ethylene dibromide and ethylene dichloride, dyes, spark plug anti-foulants such as tricresyl phosphate, dimethyl xylyl phosphate, and diphenyl cresyl phosphate, combustion modifiers such as alkyl boromic acids and lower alkyl phosphates and phos phites, oxidation inhibitors such as N,N-disecondarybutylphenylenediamine, N-n-butyl-p-aminophenol, and 2, 6-ditertiary-butyl-4-methylphenol, metal deactivators such as N,N'-
• R is selected from the group consisting of hydrogen and lower alkyl radicals, is selected from the group consisting of alkyl and alkaryl radicals containing a straight chain hydrocarbyl group of at least 6 carbon atoms, L and L each contain no more than 4 atoms.
• B is an aminonitrogen-containing radical selected from the group consisting of di-lower-alkylaminoalkyl radicals, di-lower-alkylaminoalkaryl radicals and pyridyl radicals, and wherein the ratio of x to y is from about 1:1 to about 50:1
• said polymer containing from about 0.2 to about 5% by;
• L is a carbonyloxy radical and O is an alky radical containing from 12 to 20 carbon atoms.
• a gasoline composition consisting essentially of a major amount of a hydrocarbon material boiling within the gasoline boiling range and from about 1 to about 50 parts per million by weight of an oil-soluble copolymer of lauryl methacrylate and N-beta-diethylaminoethyl methacrylate.
• An aviation gasoline composition consisting essentially of a major amount of hydrocarbons boiling within the aviation gasoline boiling range and at least about 0.1 and less than about 100 parts per million of a copolymer of lauryl methacrylate and N-beta-dimethylamino ethyl methacrylate containing from about 0.2 to about 5% by weight of amino nitrogen, having a carbon to amino nitrogen ratio of at least 20:1 and having an in! herent viscosity, determined at 0.1% concentration in benzene at 25 C., of 0.1 to 3.0 and wherein the mol ratio of lauryl methacrylate to N-beta-diethylaminoethyl methacrylate in the copolymer is about 9:1.
• An aviation gasoline composition consisting e8- sentially of a major amount of hydrocarbons boiling within the aviation gasoline boiling range and at least about 0.1 not less than about parts per million by weight of a copolymer of lauryl methacrylate and N-- beta-diethylaminoethyl methacrylate in a mol ratio respectively of from about 1:1 to about 50:1 containing from about 0.2 to about 5% by weight of amino nitrogen, having a carbon to amino nitrogen ratio of at least 20 to l and having an inherent viscosity, determined at 0.1% concentration in benzene at 25 C., of 0.1 to 3.0.

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• Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Engineering & Computer Science (AREA)
• Organic Chemistry (AREA)
• Combustion & Propulsion (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Liquid Carbonaceous Fuels (AREA)
• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Priority Applications (7)

Applications Claiming Priority (1)

Publications (1)

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ID=24197396

Family Applications (1)

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Cited By (4)

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Citations (2)

• 0
  • DE DENDAT1050111D patent/DE1050111B/de active Pending
  • NL NL212557D patent/NL212557A/xx unknown
  • NL NL101833D patent/NL101833C/xx active
  • BE BE553025D patent/BE553025A/xx unknown
• 1955
  • 1955-12-01 US US550491A patent/US2982628A/en not_active Expired - Lifetime
• 1956
  • 1956-11-28 FR FR1167856D patent/FR1167856A/fr not_active Expired
  • 1956-11-29 GB GB36543/56A patent/GB816306A/en not_active Expired

Patent Citations (2)

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