Naphthylglycidyl ether-modified polyetheramines and their use

Abstract

(a) A composition comprising a naphthylglycidyl ether-modified polyetheramine obtained by the reaction of a polyoxyalkylene monoamine and (b) naphthylglycidyl ether, and its use in various applications, although not limited to those applications, examples include as a dispersant or a deposit control additive.

Description

Technical Field

[0001] Cross - Reference to Related Applications This application claims priority to U.S. Provisional Application No. 63 / 471,611, filed on June 7, 2023. The foregoing application is incorporated herein by reference.

[0002] The present disclosure generally relates to naphthyl glycidyl ether - modified polyether amines obtained from the reaction of naphthyl glycidyl ether and polyoxyalkylene monoamines. Naphthyl glycidyl ether - modified polyether amines can be used for various applications, such as dispersants for soot, asphaltenes, pigments, graphene, and carbon nanotubes, or as deposit control additives in fuel compositions.

Background Art

[0003] During the combustion of fuel, especially gasoline, in an engine, carbonaceous products tend to form carbonaceous particles (soot), which inhibit the performance of the engine. One specific technique that has been used to control soot is to add a deposit control additive to the fuel before combustion. One commonly used type of deposit control additive is polyether amine. Typically, polyether amines are single - molecule additives that have both an amine functional group and a polyether functional group in the same molecule. Prior art polyether amines can be found in Patent Document 1, Patent Document 2, Patent Document 3, Patent Document 4, Patent Document 5, Patent Document 6, Patent Document 7, Patent Document 8, Patent Document 9, Patent Document 10, Patent Document 11, Patent Document 12, Patent Document 13, and Patent Document 14.

[0004] Nevertheless, there is a continuing need to develop new general - purpose polyether amines that can control soot and exhibit effective dispersion performance with respect to other materials such as graphene, asphaltenes, pigments, and carbon nanotubes.

Prior Art Documents

Patent Documents

[0005] [Patent Document 1] U.S. Patent No. 4,191,537 [Patent Document 2] U.S. Patent No. 4,261,704 [Patent Document 3] U.S. Patent No. 5,752,991 [Patent Document 4] U.S. Patent No. 4,985,047 [Patent Document 5] U.S. Patent No. 5,112,364 [Patent Document 6] U.S. Patent No. 4,609,377 [Patent Document 7] U.S. Patent No. 6,372,000 [Patent Document 8] U.S. Patent No. 6,217,624 [Patent Document 9] U.S. Patent No. 6,548,461 [Patent Document 10] U.S. Patent No. 4,747,851 [Patent Document 11] U.S. Patent No. 5,527,364 [Patent Document 12] U.S. Patent No. 5,660,601 [Patent Document 13] U.S. Patent No. 6,224,642 [Patent Document 14] U.S. Patent No. 6,548,461 [Overview of the Initiative]

[0006] This disclosure generally provides compositions comprising naphthylglycidyl ether-modified polyetheramines obtained by the reaction of a polyoxyalkylene monoamine with naphthylglycidyl ether. Naphthylglycidyl ether-modified polyetheramines have various applications, for example, It can be used as a dispersant for a variety of materials, including, but not limited to, soot, graphene, asphaltenes, pigments, and carbon nanotubes.

[0007] In another embodiment, naphthylglycidyl ether-modified polyetheramines can be used as deposit control additives and can be added to fuel compositions to form additive-containing fuel compositions.

[0008] In other embodiments, the disclosure provides a deposit control method in an engine and a method for improving engine performance by burning an additive-containing fuel composition in an engine. [Brief explanation of the drawing]

[0009] [Figure 1] A graph showing the relative kinematic viscosity of samples 1-3 is displayed. [Modes for carrying out the invention]

[0010] This disclosure generally relates to compositions comprising naphthylglycidyl ether-modified polyetheramines obtained from the reaction of polyoxyalkyleneamines with naphthylglycidyl ethers. Surprisingly, the naphthylglycidyl ether-modified polyetheramines of this disclosure have been found to be effectively usable as dispersants for soot, as well as for asphaltenes, pigments, graphene, and carbon nanotubes, and as deposit control additives for fuel compositions. For example, because naphthylglycidyl ether-modified polyetheramines have amine groups, they can adhere to functional groups such as carboxylic acid groups present on the soot surface, thereby stabilizing the soot into smaller, dispersible structures and thus reducing the soot's tendency to aggregate. Furthermore, it is known that soot can also contain condensed aromatic ring structures. Therefore, the adhesion force between the naphthylglycidyl ether-modified polyetheramines of this disclosure and soot can be greatly improved because the naphthyl groups can form very strong van der Waals forces with the condensed aromatic ring structures.

[0011] The following terms shall have the following meanings:

[0012] The term "comprising" and its derivatives do not intend to exclude the presence of any additional element, step, or procedure, regardless of whether they are disclosed in this specification. For the purpose of avoiding any doubt, all compositions claimed through the use of the term "comprising" in this specification may include any additional additive, adjuvant, or compound, unless there is a contrary description. In contrast, the term "consisting essentially of", when it appears in this specification, excludes any other element, step, or procedure, except when they are not essential for operation, from any subsequent scope of enumeration, and the term "consisting of", when used, excludes any element, step, or procedure that is not specifically described or enumerated. The term "or", unless otherwise specified, refers to the enumerated members individually and also to any combination.

[0013] The articles "a" and "an" are used in this specification to indicate that the grammatical object of the article refers to one or more than one (i.e., at least one). Phrases such as "in one embodiment", "in accordance with one embodiment", etc. generally mean that the specific feature, structure, or characteristic following such phrases is included in at least one aspect of the present disclosure and may also be included in more than one aspect of the present disclosure. Importantly, such phrases do not necessarily refer to the same aspect. In this specification, when the words "may" , "can", "could", or "might" are used to describe that a certain element or feature has or includes a certain feature, that particular element or feature is not required to have or include that feature.

[0014] The term "about", as used herein, allows for a degree of variability in a value or range, for example, it can be within 10%, within 5%, or within 1% of the stated value or the stated range limits.

[0015] Values expressed in range format should be interpreted in a flexible manner such that they include not only the numerical values specified as the limits of the range, but also individual numerical values or sub-ranges subsumed within that range, as if each numerical value and sub-range were explicitly recited. For example, a range such as 1-6 should be considered to specifically disclose sub-ranges such as 1-3, 2-4, 3-6, etc., as well as the individual numbers within that range, e.g., 1, 2, 3, 4, 5, and 6. This applies regardless of the width of the range.

[0016] The terms "suitable" and "preferably" refer to embodiments that can provide certain benefits under certain circumstances. However, other embodiments may also be suitable under the same or other circumstances. Moreover, the recitation of one or more suitable embodiments does not imply that other embodiments are not useful, nor is it intended to exclude other embodiments from the scope of this disclosure.

[0017] The term "soot" means a dark-colored powdery or flaky substance containing minute particles of carbon or heavy hydrocarbons. Gaseous soot contains polycyclic aromatic hydrocarbons (PAHs). Soot is produced by the incomplete combustion of organic substances such as hydrocarbon fuels. Soot particles can be mixed with metal oxides and inorganic substances and may be covered with sulfuric acid.

[0018] The term “major amount” is interpreted to mean an amount of 50% by weight or more of the total weight of the composition, for example, about 60% to about 99.5% by weight, or about 70% to about 99% by weight, or about 80% to about 98% by weight. Furthermore, as used herein, the term “minor amount” is interpreted to mean an amount of less than 50% by weight of the total weight of the composition, for example, about 0.1% to about 40% by weight, or about 1% to about 30% by weight, or about 5% to about 20% by weight.

[0019] The term "alkyl" refers to the monovalent radical of an alkane. A suitable alkyl group may have, for example, up to about 40 carbon atoms, or up to 24 carbon atoms, or up to 20 carbon atoms, or up to 16 carbon atoms, or up to 12 carbon atoms, or up to 10 carbon atoms, or up to 8 carbon atoms, or up to 6 carbon atoms, or up to 4 carbon atoms, or up to 3 carbon atoms. In some embodiments, an alkyl group may have, for example, 1 to 40 carbon atoms, or 2 to 30 carbon atoms, or 3 to 24 carbon atoms, or 8 to 14 carbon atoms. Alkyl groups may be linear, branched, cyclic, or a combination thereof.

[0020] When used herein, “deposit control,” “deposit control,” etc., are intended to encompass one or more of the following: reducing existing deposits (“clean up”); reducing deposit formation (“keep clean”); and modifying them to reduce the negative effects of deposits. Examples of deposits, but not limited to, include soot.

[0021] If substituents are specified by their usual chemical formulas and written from left to right, such substituents also equally encompass chemically identical substituents that can be obtained by writing their structure from right to left; for example, -CH2O- is equivalent to -OCH2-.

[0022] The terms "optional" or "optional" mean that the event or situation described below may or may not occur, and that the description includes both cases in which the event or situation occurs and cases in which it does not occur.

[0023] According to one embodiment, naphthylglycidyl ether-modified polyetheramines can be obtained by the reaction of (a) a polyoxyalkylene monoamine and (b) naphthylglycidyl ether.

[0024] In one embodiment, a polyoxyalkylene monoamine is a compound having one amino group bonded to the end of a polyether skeleton. The amino group can be either a primary (-NH2) amino group or a secondary (-NH-) amino group. In one embodiment, the amino group is a primary amino group. As will be further discussed below, the polyether skeleton is based on, i.e., defined by, alkylene oxide groups, e.g., propylene oxide (PO), ethylene oxide (EO), butylene oxide (BO), and mixtures thereof. In mixed structures, the ratio can be any desired ratio and can be arranged in blocks (e.g., repeating or alternating) or randomly distributed. In one non-limiting example, in a mixed EO / PO structure, the EO:PO ratio can range from about 1:1 to about 1:50, and vice versa. Thus, a polyoxyalkylene monoamine can substantially define polyethylene oxide, polypropylene oxide, and / or polybutylene oxide. The molecular weight of the polyoxyalkylene monoamine is variable and can range up to about 6,000 daltons. According to one embodiment, the molecular weight of the polyoxyalkylene monoamine can be from about 500 daltons to about 6,000 daltons. In another specific embodiment, the polyoxyalkylene monoamine can have a molecular weight from about 600 daltons to about 3,000 daltons.

[0025] Furthermore, in some embodiments in which the naphthylglycidyl ether-modified polyetheramines of this disclosure are prepared for use in highly polar systems such as aqueous media, the polyoxyalkylene monoamine (a) used to form the naphthylglycidyl ether-modified polyetheramine may have a polar group (i.e., polyethylene oxide) in a sufficiently high proportion (e.g., a much larger amount) than the nonpolar group (i.e., polypropylene and / or butylene oxide) for the purpose of achieving a sufficient level of water solubility for a particular area of ​​use. For example, the polyoxyalkylene monoamine may contain more than 50% by weight, or more than 60% by weight, or more than 75% by weight, or more than 90% by weight of ethylene oxide. Similarly, when forming naphthylglycidyl ether-modified polyetheramines for use in nonpolar systems, the polyoxyalkylene monoamine may contain nonpolar groups in a sufficiently higher proportion (e.g., in larger amounts) than polar groups, for example, propylene oxide and / or butylene oxide in amounts exceeding 50% by weight, 60% by weight, 75% by weight, or 90% by weight.

[0026] Polyoxyalkylene monoamines can generally be prepared by reacting a monovalent initiator, such as an alcohol, with ethylene and / or propylene oxide and / or butylene oxide. Following this reaction, the resulting terminal hydroxyl groups are converted to amines, thereby yielding a polyether skeleton comprising propylene oxide (PO), ethylene oxide (EO), butylene oxide (BO), or a mixture thereof, and terminal amino groups, such as a terminal primary amino group or a terminal secondary amino group, preferably a primary amino group. According to one embodiment, the alcohol can be an aliphatic alcohol having 1 to 35 carbon atoms or an aromatic alcohol having 6 to 35 carbon atoms, both of which can be further substituted with alkyl substituents, aryl substituents, arylalkyl substituents, and alkaryl substituents. In another embodiment, the alcohol is The alcohol may be an alkanol having 1 to 18 carbon atoms, or 1 to 10 carbon atoms, such as an alkanol derived from a lower alkyl group, and examples of such alkanols include methanol, ethanol, propanol, butanol, isopropanol, and butanol. In another embodiment, the alcohol may be an alkylphenol in which the alkyl substituent has 1 to 24 carbon atoms, for example, a linear or branched alkyl group of 4 to 16 carbon atoms, or an aryl-substituted phenol including mono, di, and triphenylphenol, or an arylalkylphenol, such as tristyryl(stryl)phenol, or naphthol, or an alkyl-substituted naphthol.

[0027] According to one particular embodiment, a polyoxyalkylene monoamine is a compound having the following general formula: [ka] In the formula, R is C1-C 40 Alkyl alkyl group or C1-C 40 It is an alkylphenol group; each R' is independently hydrogen, methyl, or ethyl; and n is an integer from about 1 to about 50. Specific examples include, but are not limited to, compounds having the following formulas: [ka] [ka] [ka] and CH3-[OCH2CH2] a -[OCH2CH(CH3)] b -NH2 In the formula, Me is methyl, Et is ethyl; f is an integer from about 13 to about 14; e is an integer from about 2 to about 3; a is an integer from 1 to about 45; and b is an integer from 1 to about 30. In some embodiments, the a / b ratio can be in the range of about 1 / 9 to about 4 1 / 4, for example, about 1 / 9, or about 6 / 29, or about 19 / 3, or about 3 3 / 10, or about 4 1 / 4. Examples of such polyoxyalkylene monoamines included in the above formula include JEFFAMINE® M-600, M-1000, M-2005, M-2070, FL-1000, C-100; XTJ-435; XTJ-436 amines, and SURFONAMINE® B-60, B-100, L-100, L-200, and L-207 amines.

[0028] A polyoxyalkyleneamine is reacted with naphthylglycidyl to form the naphthylglycidyl ether-modified polyetheramine of the present disclosure. In one embodiment, the naphthylglycidyl ether is 1-naphthylglycidyl ether. In another embodiment, the naphthylglycidyl ether is 2-naphthylglycidyl ether. In yet another embodiment, the naphthylglycidyl ether is a mixture of 1-naphthylglycidyl ether and 2-naphthylglycidyl ether.

[0029] Naphthylglycidyl ether-modified polyetheramines can be reacted by contacting naphthylglycidyl ether with a polyoxyalkylene monoamine at a temperature of approximately 50°C to 300°C. For example, the reaction can occur at temperatures in the range of approximately 150°C to 200°C. The reaction can also occur under pressures in the range of approximately 1 to 2000 psi. The reaction time can vary from approximately 30 minutes to approximately 6 hours. Methods for removing water by condensation can also be employed. In some embodiments, naphthylglycidyl ether and polyoxyalkylene monoamine can be reacted in a molar ratio (naphthylglycidyl ether:polyoxyalkylene monoamine) of approximately 0.9:1.1 to approximately 1.1:0.9, or approximately 0.95:1.05 to approximately 1.05:0.95, or approximately 1:1.

[0030] As discussed above, the water and unreacted reactants generated during the reaction can be removed from the composition by known methods after the reaction is complete. That is, in some embodiments, the composition may contain at least 80% by weight, or at least 85% by weight, or at least 90% by weight, or at least 95% by weight, or at least 99% by weight of naphthylglycidyl ether-modified polyetheramine, based on the total weight of the composition.

[0031] According to another embodiment, reacting naphthylglycidyl ether with a polyoxyalkylene monoamine as described above yields a naphthylglycidyl ether-modified polyetheramine containing a mixture of monoaddition and diaddition compounds as follows: [ka] In the formulas, R, R', and n are defined as described above. In some embodiments, the composition contains at least 50% by weight of the mono-adduct compound, where the weight percentage is based on the total weight of the mono-adduct compound and the di-adduct compound. In yet another embodiment, the composition contains at least 60% by weight, or at least 70% by weight, or at least 80% by weight, or at least 90% by weight, or at least 95% by weight of the mono-adduct compound, where the weight percentage is based on the total weight of the composition.

[0032] In another embodiment, a composition comprising the naphthylglycidyl ether-modified polyetheramine of the present disclosure can be further diluted with water and / or solvent(s) to form an aqueous or non-aqueous composition of desired strength. That is, in one embodiment, an aqueous or non-aqueous composition is provided containing the naphthylglycidyl ether-modified polyetheramine of the present disclosure, water and / or other solvents, and optionally one or more of the auxiliary agents described below. The amount of water and / or solvent present can be, for example, about 0.5% by weight to about 50% by weight, based on the total weight of the aqueous or non-aqueous composition. Thus, the amount of naphthylglycidyl ether-modified polyetheramine (and optional auxiliary agents) contained in the aqueous or non-aqueous composition can range from about 50% by weight to a maximum of about 99.5% by weight, based on the total weight of the aqueous or non-aqueous composition.

[0033] As described above, water can be added to the composition, and in some embodiments, the water is deionized water. In other embodiments, a solvent can be added to the composition in addition to or instead of water. Examples of such solvents include, but are not limited to, hydrocarbons (e.g., pentane or hexane), halocarbons (e.g., Freon 113), ethers (e.g., ethyl ether (Et2O), tetrahydrofuran ("THF"), or diglyme (diethylene glycol dimethyl ether)), nitriles (e.g., CH3CN), or aromatic compounds (e.g., benzotrifluoride). Further examples of solvents include lactic acid esters, pyruvate, and diols. Other examples of solvents include, but are not limited to, acetone, 1,4-dioxane, 1,3-dioxolane, ethyl acetate, cyclohexanone, acetone, 1-methyl-2-pyrodidianon (NMP), and methyl ethyl ketone. Other solvents include dimethylformamide, dimethylacetamide, N-methylpyrrolidone, ethylene carbonate, propylene carbonate, glycerol and its derivatives, naphthalene and its derivatives, acetic anhydride, propionic acid and propionic anhydride, dimethyl sulfone, benzophenone, diphenyl sulfone, phenol, m-cresol, dimethyl sulfoxide, diphenyl ether, and terphenyl. Further solvents include propylene glycol propyl ether (PGPE), 3-heptanol, 2-methyl-1-pentanol, 5-methyl-2-hexanol, 3-hexanol, 2-heptanol, 2-hexanol, 2,3-dimethyl-3-pentanol, propylene glycol methyl ether acetate (PGMEA), ethylene glycol, isopropyl alcohol (IPA), n-butyl ether, propylene glycol n-butyl ether (PGBE), 1-butoxy-2-propanol, and 2-methyl Examples include -3-pentanol, 2-methoxyethyl acetate, 2-butoxyethanol, 2-ethoxyethyl acetoacetate, 1-pentanol, and propylene glycol methyl ether. These solvents can be used individually or in combination.

[0034] Known additives can also be added to the composition depending on the application. Such additives include commonly used detergent additives, carrier oils, low-temperature fluidity improvers, lubricity improvers, corrosion inhibitors, deemulsifiers, dehazing agents, antifoams, cetane number improvers, combustion aids, antioxidants or stabilizers, antistatic agents, metallocenes, metal deactivators, dyes, solvents, oxygen-containing additives, anti-knock agents, colorants, pigments, enzymes, wetting agents, antifoaming agents, buffers, pH adjusters, thickeners, emulsifiers, and anti-streaking agents. Examples of such products include, but are not limited to, agents, builders, chelating agents or metal ion sequestering agents, hydrotropes, antimicrobial agents, fragrances, herbicides, insecticides, fungicides, abrasion-resistant additives, viscosity index improvers, pour point depressants, solid carriers or bulking agents, protective colloids, adhesives, humectants, repellents, attractants, feeding promoters, compatibilizers, fungicides, antifreeze agents, crystallization inhibitors, tackifiers, binders, preservatives, clarifiers, fertilizers, UV stabilizers, salts, weighting agents, gravel particles, gases, crosslinking agents, thermodynamic hydrate formation inhibitors, dynamic hydrate formation inhibitors, clay stabilizers, and mixtures thereof.

[0035] In another embodiment, a packaged product is provided comprising: a) a container having at least an outlet; and b) a composition comprising a naphthylglycidyl ether-modified polyetheramine.

[0036] In another embodiment, the packaged product of the Disclosure includes a container having a closure means for sealing the container, such as a lid, cover, cap, or stopper. In yet another embodiment, the sealed container also has a nozzle or spout. The sealed container may be cylindrical, elliptical, circular, rectangular, canister, tab, square, or jug ​​in shape and may contain the composition of the Disclosure.

[0037] In yet another embodiment, the container may be made of any material such as steel, glass, aluminum, cardboard, tinplate, or plastic, and the plastics may include, but are not limited to, high-density polyethylene (HDPE), polypropylene (PP), polyvinyl chloride (PVC), polyethylene terephthalate (PET), oriented polypropylene (OPP), polyethylene (PE), or polyamide, and may include mixtures, laminates, or other combinations thereof.

[0038] Compositions containing naphthylglycidyl ether-modified polyetheramines may be useful in a variety of applications, including, but are not limited to, deposit control additives for fuel compositions. Other applications include, but are not limited to, their use as dispersants for soot, graphene, asphaltenes, pigments, carbon nanotubes, organic and inorganic pigments, dyes, and color brighteners.

[0039] According to one embodiment, the compositions of the present disclosure are used as deposit control additives for fuel compositions. In such embodiments, the fuel composition includes a composition comprising a naphthylglycidyl ether-modified polyetheramine and a fuel, such a fuel composition is used to supply fuel to a fuel combustion system, for example, a liquid fuel engine and / or a spark-ignition engine. The types of fuel combustion systems are not excessively limited and include, but are not limited to, V-engines, inline engines, opposed-four engines and rotary engines. The engine can be a naturally aspirated engine, a boost engine, an E-boost engine, a supercharged engine, or a turbocharged engine. The engine can be a carbureted engine or a fuel-injected gasoline engine. The engine may have a carburetor or an injector (piezo injector).

[0040] In one embodiment, the engine may be a gasoline direct injection ("GDI") engine (spray or wall-injection type, or a combination thereof), a port injection ("PFI") engine, a premixed compression ignition ("HCCI") engine, a stoichiometric mixture ratio combustion engine or a lean combustion engine, a spark-controlled compression ignition ("SPCCI") engine, a variable compression ratio engine, a Miller cycle engine or an Atkinson cycle engine, or a combination thereof, such as an engine having both a GDI injector and a PFI injector in the same engine. Suitable GDI / PFI engines include two-stroke or four-stroke engines that use gasoline, a gasoline / alcohol mixture, or a fuel composition known to those skilled in the art as fuel.

[0041] In other embodiments, any of the above engines may have a mechanism for treating exhaust substances, for example, NO x A catalyst or device for reducing emissions may be provided. In other embodiments, the engine may be a flex-fuel engine capable of operating on multiple fuel types, typically gasoline and ethanol, or gasoline and methanol. In yet another embodiment, any of the above engine types may also be in a hybrid vehicle equipped with an electric motor.

[0042] In some embodiments, the fuel composition may contain a small amount of the composition containing naphthylglycidyl ether-modified polyetheramine and a majority amount of fuel. In further embodiments, the composition containing naphthylglycidyl ether-modified polyetheramine may be added directly to the fuel composition or added to the fuel composition as a component of a fuel additive concentrate, which comprises a certain amount of fuel, a carrier oil or solvent, and optionally one or more performance-enhancing additives.

[0043] The fuels suitable for use are not excessively limited and may include, for example, gasoline as specified in ASTM Standard D4814, diesel fuel as specified in ASTM Standard D975, biodiesel fuel, or any combination thereof. The fuel may also be leaded or unleaded motor and aircraft gasoline, as well as so-called reformed gasoline, which contains both hydrocarbons within the gasoline boiling point range and fuel-soluble oxygen additive blends, such as alcohols, ethers, and other suitable oxygen-containing organic compounds. Suitable oxygen-containing additives include, for example, methanol, ethanol, isopropanol, t-butanol, mixed C1-C5 alcohols, methyl tert-butyl ether, tert-amyl methyl ether, ethyl tert-butyl ether, mixed ethers, plant or animal transesterified oils and / or fats, such as rapeseed methyl ester and soybean methyl ester, and nitromethane. When used, oxygen additives are typically present in the fuel at an amount of less than approximately 25% by volume, for example, in an amount that results in an oxygen content in the total fuel ranging from approximately 0.5% to approximately 5% by volume.

[0044] The fuel may also include heavier fuel oils, such as fifth and sixth fuel oils. Fifth and sixth fuel oils are also referred to as residual fuel oil, heavy fuel oil, and / or furnace fuel oil. Such fuels can be used alone or mixed with other, typically lighter, fuels to form lower viscosity mixtures. Bunker fuel is also included, which is commonly used in marine engines. These types of fuels are highly viscous and may be solid under ambient conditions, but become liquid when heated and supplied to an engine that uses them as fuel. Other known alternative fuels are also available. These include 100% ethanol, hydrated ethanol, and 70%-85% ethanol known as "E85." You will be able to do it.

[0045] Fuel is generally present in the fuel composition in a major amount, and in some embodiments, this major amount can be more than about 90% by weight, or more than about 95% by weight, based on the total weight of the fuel composition, or in other embodiments, more than about 97% by weight, or more than about 99.5% by weight, or more than about 99.9% by weight, or even more than about 99.99% by weight.

[0046] Compositions containing naphthylglycidyl ether-modified polyetheramines are generally present in small amounts in the fuel composition, which, based on the total weight of the fuel composition, can generally be less than about 10% by weight, or less than about 1% by weight, or less than about 0.5% by weight, or even less than about 0.1% by weight (1000 ppmw) (parts per million by weight), or less than about 0.07% by weight (700 ppmw), or less than about 0.05% by weight (500 ppmw), or less than about 0.04% by weight (400 ppmw), or less than about 0.03% by weight (300 ppmw), or less than about 0.025% by weight (250 ppmw), or less than about 0.02% by weight (200 ppmw), or about 0.01% by weight (100 ppmw).

[0047] In another embodiment, the amount of composition containing naphthylglycidyl ether-modified polyetheramine in the fuel composition can be at least about 0.1 ppmw (parts per million by weight) based on the total weight of the fuel composition. In yet another embodiment, the amount of composition containing naphthylglycidyl ether-modified polyetheramine present in the fuel composition of the present disclosure can be at least about 1 ppmw, or at least about 5 ppmw, or at least about 10 ppmw, or at least about 20 ppmw, or at least about 30 ppmw, or at least about 40 ppmw, or at least about 50 ppmw, or at least about 60 ppmw, or at least about 70 ppmw, or at least about 80 ppmw, or at least about 90 ppmw, or at least about 100 ppmw, or at least about 1000 ppmw, based on the total weight of the fuel composition.

[0048] In one embodiment, a composition containing naphthylglycidyl ether-modified polyetheramine is part of a fuel additive concentrate. Such a fuel additive concentrate may optionally contain one or more performance-enhancing additives, as well as a certain amount of fuel, carrier oil, or certain solvents. The fuel additive concentrate is then added to other compositions as a convenient method for handling and transporting the composition containing naphthylglycidyl ether-modified polyetheramine to obtain the final fuel composition. The fuel additive concentrate may generally contain the composition containing naphthylglycidyl ether-modified polyetheramine in amounts of about 0.001% to about 99% by weight, or about 0.5% to about 80% by weight, or about 0.75% to about 70% by weight, or about 1% to about 60% by weight, or about 5% to about 50% by weight, or about 10% to about 40% by weight, based on the total weight of the fuel additive concentrate.

[0049] Additional performance-enhancing additives include, but are not limited to, antioxidants (e.g., in amounts of about 8-100 mg / kg of the fuel additive concentrate), such as hindered phenols or their derivatives and / or diarylamines or their derivatives; corrosion inhibitors (e.g., in amounts of about 5-100 mg / kg of the fuel additive concentrate); and / or detergent / dispersant additives, such as further polyetheramine or nitrogen-containing detergents, including, but not limited to, PIB amine detergents / dispersants, succinimide detergents / dispersants, and other quaternary salt detergents / dispersants containing quaternary ammonium imide salts (which are detergents having an imide group and a quaternary ammonium salt).

[0050] Other additional performance-enhancing additives include: low-temperature fluidity enhancers, such as maleic anhydride and styrene ester copolymers and / or ethylene and vinyl acetate. Nyl copolymers, etc.; antifoaming agents and / or defoaming agents, e.g., silicone oil, etc.; deemulsifiers, e.g., polyalkoxylated alcohols, etc.; lubricants, e.g., fatty carboxylic acids, etc.; metal deactivators, e.g., aromatic triazoles or their derivatives, including, but not limited to, benzotriazoles; and / or valve seat recession additives, e.g., alkali metal sulfosuccinates, etc.

[0051] Additional performance-enhancing additives may include: biocides; antistatic agents, de-icing agents, fluidizers, such as mineral oil and / or poly(alpha-olefin) and / or polyethers; and combustion aids (for example, in amounts of about 8 to 150 mg / kg of fuel additive concentrate), such as octane or cetane improvers.

[0052] The total amount of additional performance-enhancing additives present in the fuel additive concentrate can be less than about 50% by weight, less than about 20% by weight, less than about 10% by weight, or less than about 1% by weight, based on the total weight of the fuel additive concentrate. In other embodiments, the total amount of additional performance-enhancing additives present in the fuel additive concentrate can be at least about 0.001% by weight, at least about 0.5% by weight, at least about 2.5% by weight, at least about 5% by weight, or at least 15% by weight, based on the total weight of the fuel additive concentrate. In yet another embodiment, the total amount of additional performance-enhancing additives present in the fuel additive concentrate can be about 0.001 to 60% by weight, about 0.1 to 50% by weight, or about 1 to 40% by weight, based on the total weight of the fuel additive concentrate.

[0053] Additional performance-enhancing additives can each be added directly to the fuel additive concentrate and / or fuel composition, but generally, they are mixed with a composition containing naphthylglycidyl ether-modified polyetheramine to form a fuel additive concentrate, which is then mixed with fuel to form a fuel composition.

[0054] Fuel additive concentrates may also include carrier oils, such as inorganic carrier oils or synthetic carrier oils. Suitable inorganic carrier oils include fractions obtained from crude oil processing, such as bright stock or base oils with a viscosity of, for example, SN500 to 2000, as well as aromatic hydrocarbons, paraffinic hydrocarbons, and alkoxy alkanols. Equally useful are fractions obtained from the refining of mineral oils, known as "hydrocracking oils" (obtained by vacuum distillation cuts with a boiling point range of approximately 360°C to 500°C, or by hydrogenating and isomerizing natural mineral oils under high pressure using a catalyst, and deparaffinizing them). Equally suitable are mixtures of the above inorganic carrier oils. Examples of suitable synthetic carrier oils include polyolefins (polyalphaolefins or polyinternal olefins), (poly)esters, (poly)alkoxylates, polyethers, polyethers starting from alkylphenols, and carboxylic acid esters of long-chain alkanols.

[0055] In some embodiments, the carrier oil may be present in the fuel additive concentrate in an amount of about 0.5% to about 50% by weight, or about 2% to about 40% by weight, or about 3% to about 30% by weight, based on the total weight of the fuel additive concentrate.

[0056] The fuel additive concentrate may also contain a solvent. The solvent provides a homogeneous fuel additive concentrate and facilitates the transfer and handling of the fuel additive concentrate. In some embodiments, the solvent is an aliphatic hydrocarbon, an aromatic hydrocarbon, or a mixture thereof.

[0057] Examples of aliphatic hydrocarbons include various naphtha and kerosene boiling fractions that are mostly aliphatic. Examples of aromatic hydrocarbons include benzene, toluene, xylene, and various naphtha and kerosene boiling fractions that are mostly aromatic. In one embodiment, the solvent is in the fuel additive concentrate, based on the total weight of the fuel additive concentrate, at about 1 by weight. It can be present in amounts of approximately 90% by weight, in another embodiment, approximately 25% by weight to approximately 85% by weight, and in yet another embodiment, approximately 40% by weight to approximately 80% by weight.

[0058] Compositions containing naphthylglycidyl ether-modified polyetheramines can be added to fuel at any convenient point in the supply chain, either alone or as part of a fuel additive concentrate. For example, a composition or fuel additive concentrate containing naphthylglycidyl ether-modified polyetheramines can be added at a refinery, at a logistics terminal, or after the fuel has left the logistics terminal. When added to fuel after it has left the logistics terminal, this is called an aftermarket application. Examples of aftermarket applications include adding a composition or fuel additive concentrate containing naphthylglycidyl ether-modified polyetheramines to fuel in a delivery tanker, directly to a customer's large storage tank, or directly to the vehicle tank of the end consumer. Another example of an aftermarket application is supplying a composition or fuel additive concentrate containing naphthylglycidyl ether-modified polyetheramines in small bottles suitable for direct addition to storage tanks or vehicle tanks.

[0059] In another embodiment, the Disclosure provides a method for controlling engine deposits, comprising adding a composition comprising a naphthylglycidyl ether-modified polyetheramine and optionally a carrier oil, solvent, or performance-enhancing additive to a fuel to be burned to form an additive-containing fuel composition, and burning the additive-containing fuel composition in an engine.

[0060] In another embodiment, the Disclosure provides a method for improving engine efficiency, which comprises adding a composition comprising a naphthylglycidyl ether-modified polyetheramine and optionally a carrier oil, solvent, or performance-enhancing additive to a fuel to be burned to form an additive-containing fuel composition, and burning the additive-containing fuel composition in an engine.

[0061] In yet another embodiment, the Disclosure provides a method for improving the performance of an engine, the method comprising adding a composition comprising a naphthylglycidyl ether-modified polyetheramine and optionally a carrier oil, solvent, or performance-enhancing additive to gasoline to be burned to form an additive-containing fuel composition, and burning the additive-containing fuel composition in an engine, wherein the performance improvement is one or more of the following: improved fuel efficiency; reduced maintenance; reduced frequency of injector overhaul or replacement; improved drivability; improved power output; and improved acceleration.

[0062] The present disclosure will now be further described with reference to the following non-limiting embodiments. [Examples]

[0063] Example 1 - The naphthylglycidyl ether-modified polyetheramine of the present invention. A 500 ml three-necked flask was fitted with a mechanical stirrer, thermocouple, and condenser. 250 g (0.25 mol) of Surfonamine® B-100 amine, 3.0 g of deionized water, and 54.5 g of 2-naphthylglycidyl ether were added. The mixture was heated to 170°C and reacted at 170°C for 4 hours. Water was then removed under conditions of 90°C / 20 torr / 2 hours. LC-MS analysis of the adduct showed that the mono-adduct product was present in an amount of >90% by weight, along with small amounts of the di-adduct product and unreacted Surfonamine® B-100 amine. The mono-adduct product has the following structure: [ka]

[0064] Example 2 - Naphthylglycidyl ether-modified polyetheramine of the present invention. A mechanical stirrer, thermocouple, and condenser were fitted into a 500 ml three-necked flask, and 212.8 g (0.1 mol) of Surfonamine® L-200 amine, 2.4 g of deionized water, and 21.8 g of 2-naphthylglycidyl ether were added. The mixture was heated to 170°C and reacted at 170°C for 4 hours. Then, water was removed under conditions of 90°C / 20 torr / 2 hours. LC-MS analysis of the adduct showed that the mono-adduct product was present in an amount of >90 wt%, along with small amounts of di-adduct product and unreacted Surfonamine® L-200 amine. The mono-adduct product has the following structure: [ka]

[0065] Example 3 - Dispersion Test Results

[0066] Using the polyetheramine and Surfonamine® B-100 from Example 1, carbon black was dispersed in paraffin oil. The kinematic viscosity of the dispersion system at 40°C was measured using a Brookfield viscometer. Lower viscosity indicates better dispersion effect of the dispersant. The dispersion system of Example 3 is shown in Table 1A below.

[0067] [Table 1]

[0068] Samples 1-3 were thoroughly stirred on a vibrator to ensure even dispersion. The kinematic viscosity of each sample (1-3) was measured as described above. The results are shown in Table 1 and Figure below. [Table 2]

[0069] As shown in the figure, the polyetheramine in Example 1 results in improved dispersion of carbon black.

[0070] Although various embodiments of the present invention have been described in detail above, it goes without saying that the present invention provides many applicable concepts that can be realized in a wide range of specific situations. The specific embodiments discussed herein are merely illustrative of specific ways of creating and using the present invention and do not define the scope of the invention.

Claims

1. The following reactions: (a) Polyoxyalkylene monoamines and (b) Naphthylglycidyl ether A composition comprising a naphthylglycidyl ether-modified polyetheramine obtained by the method described above.

2. The polyoxyalkylene monoamine is a compound having the following general formula: 【Chemistry 1】 In the formula, R is C １ -C ４０ Alkyl alkyl group or C １ -C ４０ The composition according to claim 1, wherein the group is an alkylphenol group; each R' is independently hydrogen, methyl, or ethyl; and n is an integer from about 1 to about 50.

3. The polyoxyalkylene monoamine is given by the following formula: 【Chemistry 2】 ; or the following formula: 【Transformation 3】 ; or the following formula: 【Chemistry 4】 ; or the following formula: CH ３ -[[[H ２ CH ２ ] ａ -[[[H ２ HH(H) ３ )] ｂ -NH ２ It is a compound having The composition according to claim 2, wherein Me is methyl and Et is ethyl; f is an integer from about 13 to about 14; e is an integer from about 2 to about 3; a is an integer from 1 to about 45; and b is an integer from 1 to about 30.

4. The composition according to claim 3, wherein the a / b ratio is in the range of about 1 / 9 to about 4 1 / 4.

5. The composition according to claim 1, wherein the naphthylglycidyl ether is 1-naphthylglycidyl, 2-naphthylglycidyl ether, or a mixture thereof.

6. The naphthylglycidyl ether-modified polyetheramines are mono-addition and di-addition compounds as follows: 【Transformation 5】 In the formula, R, R', and n are defined in claim 1. The composition according to claim 5, comprising a mixture of the following.

7. The composition according to claim 1, further comprising water, a solvent, an auxiliary agent, or a mixture thereof.

8. A dispersion composition comprising the composition described in claim 1, and at least one of soot, graphene, asphaltene, pigment, and carbon nanotube.

9. A method for forming the composition according to claim 1, comprising reacting (a) the polyoxyalkylene monoamine and (b) naphthylglycidyl ether at a temperature of about 150°C to 200°C.

10. A fuel additive concentrate comprising the composition described in claim 1, a carrier oil or solvent, and optionally one or more performance-enhancing additives.

11. The fuel additive concentrate according to claim 10, wherein the carrier oil includes an inorganic carrier oil or a synthetic carrier oil.

12. The fuel additive concentrate according to claim 10, wherein the solvent comprises an aliphatic hydrocarbon, an aromatic hydrocarbon, or a mixture thereof.

13. A fuel composition comprising a small amount of the composition described in claim 1 and a main amount of fuel.

14. The fuel composition according to claim 13, wherein the fuel includes gasoline.

15. The fuel composition according to claim 13, wherein the fuel composition is added to the fuel after the fuel has left the logistics terminal.

16. A method for controlling deposits in an engine, comprising: adding the composition described in claim 1 and optionally a carrier oil, a solvent, or one or more performance-enhancing additives to a fuel to be burned to form an additive-containing fuel composition; and burning the additive-containing fuel composition in the engine.

17. The method according to claim 16, wherein the fuel includes gasoline, and the engine is a gasoline direct injection engine.

18. A method for improving the performance of an engine, comprising: adding the composition described in claim 1 and optionally a carrier oil, a solvent, and one or more performance-enhancing additives to gasoline to be burned to form an additive-containing fuel composition; and burning the additive-containing fuel composition in the engine, wherein the improvement in performance is one or more of the following: improved fuel efficiency; reduced maintenance; reduced frequency of injector overhaul or replacement; improved drivability; improved power output; and improved acceleration.

Images