Reaction products of organic amines and glycidol, and their use as friction modifiers.

Abstract

The present disclosure generally relates to friction modifiers comprising the reaction product of an organic amine and glycidol and their use in non-aqueous lubricant compositions. A method for reducing friction between sliding parts of an engine by contacting the engine with the non-aqueous lubricant composition is also provided.

Description

[Technical Field] 【0001】 Cross-reference of related applications This application claims priority to U.S. Provisional Application No. 63 / 126,112, filed December 16, 2020. The application(s) described herein are incorporated herein by reference. 【0002】 Description of research and development funded by the federal government. Not applicable. 【0003】 This disclosure generally relates to friction modifiers comprising (i) an organic amine selected from alkylamines, alicyclic amines, arylamines, alkylalkoxylated monoamines, and mixtures thereof, and (ii) glycidol, as well as their use in non-aqueous lubricant compositions for reducing friction between sliding parts of an engine. [Background technology] 【0004】 Engine oil plays a crucial role in lubricating various sliding parts within the engine, including, for example, piston rings / cylinder liners, crankshaft and connecting rod bearings, and valve mechanisms (e.g., cams and valve lifters). Engine oil can also play a role in cooling the engine, dispersing combustion products, and preventing rust and corrosion. 【0005】 Engine oil is primarily intended to prevent wear and seizure of engine components. Lubricated engine components are primarily under fluid lubrication. On the other hand, the valve system and the top and bottom dead centers of the piston may be under boundary lubrication and / or thin-film lubrication. Friction between such engine components leads to significant energy loss, which can reduce fuel efficiency. To improve fuel efficiency, friction between engine components (e.g., the valve system and piston components) must be reduced. 【0006】 Organic friction modifiers are generally long molecules having a straight hydrocarbon chain consisting of at least 10 carbon atoms and a polar group located at one end. The polar end group is one of the factors that influence the effectiveness of the molecule as a friction modifier. Common organic friction modifiers include esters of fatty acids and polyhydric alcohols, fatty acid amides, fatty acid-derived amines, and organic dithiocarbamates or dithiophosphate compounds. For example, Patent Documents 1, 2, 3, 4, and 5 disclose various organic friction modifiers used in lubricants. Glycerol monooleate (GMO) is one of the most commonly used organic friction modifiers in engine lubricant compositions, as described in Patent Documents 6, 7, 8, 9, and 10, among others. 【0007】 Given the increasing demands for fuel efficiency in engines, there remains a need to further reduce friction and improve fuel efficiency in internal combustion engines using lubricant compositions. Therefore, it is desirable to improve the friction-reducing performance of known friction modifiers (such as glycerol monooleate) that are commonly used in this art. [Prior art documents] [Patent Documents] 【0008】 [Patent Document 1] European Patent Application Publication EP1367116 [Patent Document 2] European Patent Application Publication EP0799883 Specification [Patent Document 3] European Patent Application Publication EP0747464 Specification [Patent Document 4] U.S. Patent No. 3,933,659 [Patent Document 5] European Patent Application Publication EP335701 Specification [Patent Document 6] U.S. Patent No. 5,885,942 [Patent Document 7] U.S. Patent No. 5,866,520 [Patent Document 8] U.S. Patent No. 5,114,603 [Patent Document 9] U.S. Patent No. 4,957,651 [Patent Document 10] U.S. Patent No. 4,683,069 [Summary of the Invention] 【0009】 The present disclosure relates to a friction modifier comprising a reaction product of (i) an amine selected from alkylamines, cycloalkylamines, arylamines, alkyl alkoxylated monoamines, and mixtures thereof, and (ii) glycidol. The friction modifier can be combined with a base oil to form a non-aqueous lubricant composition for use in lubricating an engine. 【0010】 Also provided is a method for reducing friction between sliding parts by contacting at least one of the sliding parts of an engine with the non-aqueous lubricant composition. 【0011】 Finally, a friction reducing additive package comprising the reaction product of the present disclosure and one or more additives is provided. [Brief Description of the Drawings] 【0012】 [Figure 1] Shows the coefficient of friction at 130 °C when a commercially available oil is used alone or in combination with the friction modifier of the present invention. [Figure 2] Shows the coefficient of friction at 130 °C when a commercially available oil is used alone or in combination with the friction modifier of the present invention. [Modes for Carrying Out the Invention] 【0013】 The following terms shall have the following meanings. 【0014】 The term "comprising" and its derivatives, whether or not the same are disclosed herein, are not intended to exclude the presence of any additional components, steps, or procedures. To state this without any doubt, all compositions claimed herein through the use of the term "comprising" may include any additional additive or compound, provided there is no conflicting description. In contrast, when the term "consisting essentially of" is used herein, this term excludes any other component, step, or procedure from the scope of any subsequent description, except for those that are not essential to the practicability. When the term "consisting of" is used, this term excludes any component, step, or procedure that is not specifically described or enumerated. The term "or" refers to the listed members individually as well as in any combination, unless otherwise stated. 【0015】 The articles "a" and "an" are used herein to refer to one or more (i.e., at least one) of the grammatical objects of the article. By way of example, "a friction modifier" means one friction modifier or more than one friction modifier. The phrases "in one embodiment", "according to one embodiment", and the like generally mean that the particular feature, structure, or property following such phrase is included in at least one embodiment of the present disclosure and may also be included in more than one embodiment of the present disclosure. Importantly, such phrases do not necessarily refer to the same embodiment. When the description herein includes "may", "can", "could", or "might" that a particular component or feature is included or has the property, it is not necessary that the particular component or feature be included or have the property. It is not necessary that a particular component or feature be included or have the property. 【0016】 The term "about" used herein allows for some variation in a value or range, for example, the degree of this variation may be within 10%, 5%, or 1% of the recited value or the limit values of the recited range. 【0017】 Values ​​expressed in range format shall be interpreted in a flexible manner to include not only the numerical value explicitly stated as the limit of the range, but also all individual numerical values ​​or subranges contained within that range, as if each numerical value and subrange were explicitly stated. For example, a range (e.g., 1-6) shall be considered to specifically disclose subranges (e.g., 1-3, 2-4, 3-6) and the individual digits within that range (e.g., 1, 2, 3, 4, 5, and 6). This applies regardless of the width of the range. 【0018】 The terms “preferred” and “preferred” indicate that, under certain circumstances, an embodiment may provide certain benefits. However, under the same or other circumstances, other embodiments may also be preferred. Furthermore, the description of one or more preferred embodiments does not imply that other embodiments are unhelpful, nor is it intended to exclude other embodiments from the scope of this disclosure. 【0019】 The term "substantially absent" means that the amount of a particular compound or part present in the composition does not significantly affect the composition. In some embodiments, "substantially absent" may mean that the amount of a particular compound or part present in the composition is less than 2% by weight, or less than 1% by weight, or less than 0.5% by weight, or less than 0.1% by weight, or even less than 0.01% by weight, based on the total weight of the composition, or that the amount of that particular compound or part present in each composition is none. 【0020】 When a substituent is identified by its usual chemical formula (written from left to right), such substituents equally encompass chemically identical substituents that would be assumed to be obtained by writing the structure from right to left; for example, -CH2O- is equivalent to -OCH2-. 【0021】 The term "alkyl" refers to a linear or branched saturated hydrocarbon group having 1 to approximately 100 carbon atoms. In some embodiments, the alkyl substituent may be a lower alkyl group. The term "lower" refers to an alkyl group having 1 to 3 carbon atoms. Examples of "lower alkyl groups," but not limited to, include methyl, ethyl, n-propyl, and i-propyl. 【0022】 The term "alicyclic" refers to alicyclic substituents known in the art that may have approximately 3 to approximately 12 ring carbon atoms or approximately 3 to approximately 10 ring carbon atoms, and such alicyclic substituents include, but are not limited to, cyclopentyl and cyclohexyl. 【0023】 The term "aryl" refers to aryl substituents or aryl functional groups known in the art, such aryl substituents or aryl functional groups include, but are not limited to, any substituent or functional group derived from an aromatic ring (including, but not limited to, phenyl, naphthyl, thienyl, and indolyl, and similar). An aryl group may be a ring substituted with one or more alkyl groups. 【0024】 The terms “optional” or “optional” mean that the event or situation described thereafter may or may not occur, and that the description includes both cases in which such event or situation occurs and cases in which it does not occur. 【0025】 This disclosure generally relates to friction modifiers comprising (i) an organic amine selected from alkylamines, alicyclic amines, arylamines, alkylalkoxylated monoamines, and mixtures thereof, and (ii) a reaction product of glycidol. 【0026】 This disclosure also relates to a friction-reducing additive package comprising the friction modifiers and one or more additives disclosed herein. 【0027】 This disclosure further relates to a non-aqueous lubricant composition comprising a base oil and a friction modifier disclosed herein. 【0028】 This disclosure also relates to a method for reducing friction in an engine by bringing the engine's sliding parts into contact with a non-aqueous lubricant composition. 【0029】 It has been shown that combining the friction modifier of this disclosure with a base oil forms a non-aqueous lubricant composition, which increases the lubricity of the non-aqueous lubricant composition and, consequently, significantly reduces wear on engine surfaces, engine parts, components, or engine components that are in contact with or in contact with the non-aqueous lubricant composition, which is remarkable. 【0030】 According to one embodiment, the organic amine is an alkylamine having the formula N(R1)3, where each R1 is hydrogen or an alkyl group, provided that at least one R1 is hydrogen. In one embodiment, at least one R1 is C1-C 50 Alkyl or C1-C 30 It is an alkyl group. Examples of alkylamines, but are not limited to, include ethylamine, propylamine, isopropylamine, butylamine, ethylenediamine, dipropylamine, octamethylenediamine, octylamine, tetramethylethylenediamine, tridecylamine, 2-ethylhexylamine, tetraethylenepentamine, hexamethylenediamine, dodecylamine, cocoamine, oleylamine, tallowamine, pentadecylamine, stearylamine, and soybeanamine. 【0031】 In another embodiment, the organic amine is an alicyclic amine. Examples of alicyclic amines include, but are not limited to, cyclopentylamine, cyclohexylamine, cycloheptylamine, cyclododecylamine, 4-methylcyclohexylamine, N,N-dimethylcyclohexylamine, hexamethyleneimine, piperidine, and isophoronediamine. 【0032】 In another embodiment, the organic amine is an arylamine. Examples of arylamines include, but are not limited to, aniline, diaminotoluene, diphenylalanine, N-phenylbenzamine, and toluidine. In another embodiment, the arylamine is C1-C 50 Base or C1-C 20 It is replaced by an alkyl group. 【0033】 In yet another embodiment, the organic amine is an alkylalkoxylated monoamine containing one amino group attached to the terminus of a mono or polyether skeleton. As will be discussed further below, the mono or polyether skeleton is based on, i.e., further defined by, an alkylene oxide group (such as 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 block units (e.g., repeating or alternating) or randomly distributed. In a non-limiting example, in a mixed EO / PO structure, the EO:PO ratio can be about 1:1 to about 1:50, and vice versa. Thus, the alkoxylated monoamine is a mono or polyethylene oxide This can substantially define mono- or polypropylene oxides and / or mono- or polybutylene oxides. The molecular weight of the alkylalkoxylated monoamines can vary, and can range up to about 6000. 【0034】 In one particular embodiment, the alkylalkoxylated monoamine has the basic formula: [ka] It is a compound having the following properties: In the formula, Z is an alkyl group, an alicyclic group, or an aryl group, Z' is independently hydrogen, methyl, or ethyl, and e is an integer from about 1 to about 100. In some embodiments, Z is C1-C 40 Alkyl or C1-C 20 It is the base. In yet another embodiment, Z is C1-C40 Alkyl or C1-C 20 It is an aryl group optionally substituted with an alkyl group. In yet another embodiment, e is an integer between about 1 and about 50, or between about 1 and about 20, or between about 1 and about 15. Specific examples, but not limited to, include formulas such as: [ka] Examples of compounds having the following characteristics: In the formula, Me is methyl, Et is ethyl, f is an integer between approximately 13 and approximately 14, and e is an integer between approximately 2 and approximately 3. Such polyoxyalkyles are included in the above formula. The monoamines include JEFFAMINE®: M-600 amine having formula (1) with a molecular weight of approximately 600 and a PO / EO molar ratio of 9 / 1; M-1000 amine having formula (1) with a molecular weight of approximately 1000 and a PO / EO molar ratio of 3 / 19; M-2005 having formula (1) with a molecular weight of approximately 2000 and a PO / EO molar ratio of 29 / 6; M-2070 amine having formula (1) with a molecular weight of approximately 2000 and a PO / EO molar ratio of 10 / 31; FL-1000 amine having formula (3) with f = 14 and Me or Et = methyl; C-300 amine having formula (4) with e = approximately 2.5; XTJ-435 amine having formula (2); and XTJ-436 amine having formula (3) with Me or Et = methyl and f = approximately 13.5. 【0035】 Depending on the starting materials, the reaction between the organic amine and glycidol may be carried out at a temperature in the range of about 25°C to about 300°C and a pressure of about 1 psi to about 2000 psi for about 0.5 hours to 24 hours. In one embodiment, the temperature is maintained in the range of about 125°C to about 175°C. The reaction may be carried out with a molar ratio of organic amine to glycidol of about 0.1 to about 2. In another embodiment, the amounts of organic amine and glycidol are selected so as to produce at least one reaction product (or compound) having the following formula: Amine mono-glycidol reaction products [ka] [Chemical formula] In the formula, Z, Z', and e are as defined above. In one embodiment, R is a C1-C 50 alkyl group or a C1-C 25 alkyl group. In another embodiment, R is a cyclopentyl group or a cyclohexyl group. In yet another embodiment, R is a phenyl group or a phenyl group substituted with a C1-C 20 alkyl group. In yet another embodiment, R is an alkyl alkoxylate group, Z is a C1-C 20 alkyl group, each Z' is independently hydrogen or methyl, and e is an integer from about 1 to about 50 or from about 1 to about 25. Thus, in one embodiment, the friction modifier is selected from a compound having formula (5), a compound having formula (6), a compound having formula (7), a compound having formula (8) , a compound having formula (9), and mixtures thereof. In a preferred embodiment, the friction modifier comprises at least one of 2,3-dihydroxypropylamine, 1,3-dihydroxypropylamine, bis(2,3-dihydroxypropyl)amine, bis(1,3-dihydroxypropyl)amine, and (2,3-dihydroxypropyl)(1,3-dihydroxypropyl)amine. 【0036】 The reaction products of the present disclosure have been found to be surprisingly useful as friction modifiers in non-aqueous lubricant compositions. Accordingly, the present disclosure also provides a non-aqueous lubricant composition comprising a base oil and a friction modifier comprising a reaction product according to the present disclosure. 【0037】 According to one embodiment, the total amount of base oil included in the non-aqueous lubricant composition can be at least about 50 wt%, or at least 60 wt%, or at least 70 wt%, or at least 80 wt%, or at least 90 wt%, or at least about 95 wt% based on the total weight of the non-aqueous lubricant composition. 【0038】 In another embodiment, the amount of base oil included in the non-aqueous lubricant composition may be in the range of about 50% to about 99% by weight relative to the total weight of the non-aqueous lubricant composition; in yet another embodiment, it may be in the range of about 60% to about 92% by weight; in yet another embodiment, it may be in the range of about 70% to about 90% by weight; and in yet another embodiment, it may be in the range of about 75% to about 88% by weight. 【0039】 In another embodiment, the total amount of friction modifiers, including the reaction products of the present disclosure, included in the non-aqueous lubricant composition is in the range of about 0.0001% to about 20% by weight relative to the total weight of the non-aqueous lubricant composition; in yet another embodiment, it is in the range of about 0.001% to about 10% by weight; in yet another embodiment, it is in the range of about 0.01% to about 5% by weight; and in yet another embodiment, it is in the range of about 0.1% to about 1.5% by weight. 【0040】 In some embodiments, the base oils that may be used in this disclosure include known synthetic oils and mineral oils and mixtures thereof. 【0041】 Examples of synthetic oils include dicarboxylic acids, polyglycols, alkyl esters of alcohols, poly-alpha-olefins (including polybutene), alkylbenzenes, organic esters of phosphoric acid, and polysilicone oils. Synthetic oils also include hydrocarbon oils, such as polymerized and copolymerized olefins (e.g., polybutylene, polypropylene, propylene-isobutylene copolymer, etc.); poly(l-hexene), poly-(l-octene), poly(l-decene), etc., and mixtures thereof; alkylbenzenes (e.g., dodecylbenzene, tetradecylbenzene, di-nonylbenzene, di-(2-ethylhexyl)benzene, etc.); polyphenyls (e.g., biphenyl, terphenyl, alkylated polyphenyl, etc.); alkylated diphenyl ethers and alkylated diphenyl sulfides, as well as their derivatives, analogs, and homologs, and similar compounds. 【0042】 Alkylene oxide polymers and alkylene oxide copolymers, as well as their derivatives modified by esterification, etherification, etc., constitute another class of known synthetic oils that can be used. Such oils include oils prepared via polymerization of ethylene oxide or propylene oxide, alkyl ethers and aryl ethers of such polyoxyalkylene polymers (e.g., methyl-polyisopropylene glycol ether with an average molecular weight of about 1000, diphenyl ether of polyethylene glycol with a molecular weight of about 500-1000, diethyl ether of polypropylene glycol with a molecular weight of about 1000-1500, etc.), or their mono and polycarboxylic acids. Examples include esters (e.g., tetraethylene glycol acetate, mixed C3-C8 fatty acid esters, or oxoacid diesters). 【0043】 Another class of synthetic oils that may be used includes esters of dicarboxylic acids (e.g., phthalic acid, succinic acid, alkyl succinic acid, alkenyl succinic acid, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, alkyl malonic acid, alkenyl malonic acid, etc.) with various alcohols (e.g., butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol, diethylene glycol monoether, propylene glycol, etc.). Specific examples of such esters include dibutyl adipate, di-](2-ethylhexyl) sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, 2-ethylhexyl diesters of linoleic acid dimers, complex esters formed by reacting 1 mole of sebaciic acid with 2 moles of tetraethylene glycol and 2 moles of 2-ethylhexanoic acid, and similar products. 【0044】 Esters useful as synthetic oils include C5-C 12This also includes products prepared from monocarboxylic acids and polyols and polyol ethers (such as neopentyl glycol, trimethylolpropane, pentaerythritol, dipentaerythritol, and tripentaerythritol). 【0045】 The base oil may contain small or large amounts of poly-alpha-olefin (PAO). Typically, poly-alpha-olefins are obtained from monomers having about 4 to about 30 carbon atoms, or about 4 to about 20 carbon atoms, or about 6 to about 16 carbon atoms. Examples of useful PAOs include those obtained from octene, decene, and mixtures thereof, as well as similar ones. PAOs may have viscosities of about 2 to about 15 centistokes (cSt), or about 3 to about 12 cSt, or about 4 to about 8 cSt at 100°C. Examples of PAOs include poly-alpha-olefins with a viscosity of 4 cSt at 100°C, poly-alpha-olefins with a viscosity of 6 cSt at 100°C, and mixtures thereof. Mixtures of mineral oil and the aforementioned PAOs may be used. 【0046】 The base oil may be an oil obtained from hydrocarbons synthesized by the Fischer-Tropsch process. Hydrocarbons synthesized by the Fischer-Tropsch process are prepared from synthesis gas containing H2 and CO using a Fischer-Tropsch catalyst. Such hydrocarbons typically require further processing to be useful as base oils. For example, such hydrocarbons may be hydrogen-isomerized using the process disclosed in U.S. Patent No. 6,103,099 or No. 6,180,575, or hydrocracking and hydrogen-isomerized using the process disclosed in U.S. Patent No. 4,943,672 or No. 6,096,940, or dewaxed using the process disclosed in U.S. Patent No. 5,882,505, or hydrogen-isomerized and dewaxed using the process disclosed in U.S. Patent No. 6,013,171, No. 6,080,301, or No. 6,165,949. 【0047】 Any type of mineral oil or synthetic oil disclosed herein (and any mixture of two or more of these) may be used as a base oil as unrefined oil, refined oil, and re-refined oil. Unrefined oil is obtained directly from a natural or synthetic source without further refining. For example, shale oil obtained directly from a retort operation, petroleum obtained directly from primary distillation, or ester oil obtained directly from an esterification process are considered unrefined oils if used without further processing. Refined oil is similar to unrefined oil, but differs in that it is further processed in one or more refining steps to improve one or more properties. Many such refining methods are known to those skilled in the art, and such refining The methods include solvent extraction, secondary distillation, acid or base extraction, filtration, and percolation. Refined oil is obtained by applying the same processes used to obtain refined oil to already used refined oil. Such refined oil is also known as recycled oil or reprocessed oil and is often further treated by methods aimed at removing used additives, contaminants, and oil degradation products. 【0048】 Mineral oils include liquid petroleum, as well as paraffinic, naphthenic, or mixed paraffinic / naphthenic solvent-treated or acid-treated mineral oil lubricants, which may be further refined by a hydrogenation finishing process and / or dewaxing. 【0049】 Naphthenic base oils have a low viscosity index (VI) (generally 40-80) and a low pour point. Such base oils are produced from raw materials with a high naphthene content and a low wax content, and are mainly used in lubricants where color and color stability are important, and viscosity index (VI) and oxidation stability are secondarily important. 【0050】 Paraffin-based base oils have high VI (generally above 95) and high pour points. These base oils are produced from raw materials with high paraffin content and are used in lubricants where VI and oxidation stability are important. 【0051】 In some embodiments, the base oil consists of mineral and / or synthetic oils containing more than 80% by weight of saturation as measured according to ASTM D2007, and in other embodiments, more than 90% by weight. In other embodiments, the base oil contains less than 1.0% by weight of sulfur as measured according to ASTM D2622, ASTM D4294, ASTM D4927, or ASTM D3120 and calculated as elemental sulfur, and in yet other embodiments, less than 0.1% by weight. 【0052】 Those skilled in the art will readily understand that the viscosity of the base oil depends on its application. Therefore, the viscosity of the base oil for use herein can typically be about 2 cSt to about 2000 cSt at 100°C. Generally, the kinematic viscosity at 100°C of base oils used as engine oils individually ranges from about 2 cSt to about 30 cSt, in some embodiments from about 3 cSt to about 16 cSt, and in other embodiments from about 4 cSt to about 12 cSt. The base oils are selected or blended depending on the desired end use and the additives to be included in the finished oil to obtain the desired grade of engine oil, such as lubricant compositions having SAE viscosity grades of 0W, OW-20, 0W-30, OW-40, OW-50, OW-60, 5W, 5W-20, 5W-30, 5W-40, 5W-50, 5W-60, 10W, 1OW-20, 10W-30, 1OW-40, 1OW-50, 15W, 15W-20, 15W-30, or 15W-40. Base oils used as gear oils can have a viscosity of approximately 2 cSt to 2000 cSt at 100°C. 【0053】 Non-aqueous lubricant compositions can be used to lubricate virtually any spark-ignition or compression-ignition internal combustion engine. Such internal combustion engines include automobile and truck engines, two-stroke engines, diesel engines, aircraft piston engines, marine and railway engines, and similar types. Non-aqueous lubricant compositions are also intended for gas combustion engines, alcohol (e.g., methanol) power engines, fixed-power engines, turbines, and similar types. Non-aqueous lubricant compositions can also be used as automatic transmission fluids, gear lubricants, compressor lubricants, metalworking lubricants, or working fluids. 【0054】 The non-aqueous lubricant composition may further contain additional additives, such additional additives may include antioxidants, wear-resistant additives, surfactants, dispersants, and one or more other friction modifiers. These include friction modifiers, viscosity index improvers, pour point depressants, corrosion inhibitors, defoamers, and seal fixatives or seal conformers, as well as mixtures thereof. Examples of such additives can be found, for example, in U.S. Patent Nos. 5,498,809 and 7,696,136 (the relevant portions of each disclosure are incorporated herein by reference), but those skilled in the art will understand that this is only a small list of available lubricant additives. It is also well known that a single additive may have the ability to impart or improve multiple properties; for example, an anti-wear agent may also function as a fatigue-resistant and / or extreme-pressure additive. 【0055】 Antioxidants that can be conveniently used include those selected from the group of amine-based antioxidants and / or phenol-based antioxidants. In one embodiment, the antioxidant is present in an amount ranging from 0.1% to about 5.0% by weight based on the total weight of the non-aqueous lubricant composition, while in other embodiments, it is present in an amount ranging from 0.3% to about 3.0% by weight. 【0056】 Examples of amine-based antioxidants that can be conveniently used include alkylated diphenylamine, phenyl-α-naphthylamine, phenyl-p-naphthylamine, and alkylated α-naphthylamine. 【0057】 In one embodiment, the amine-based antioxidants include dialkyldiphenylamines (p,p'-dioctyl-diphenylamine, p,p'-di-a-methylbenzyl-diphenylamine, and Np-butylphenyl-N-p'-octylphenylamine, etc.), monoalkyldiphenylamines (mono-t-butyldiphenylamine and monooctyldiphenylamine, etc.), bis(dialkylphenyl)amines (di-(2,4-diethylphenyl)amine and di(2-ethyl-4-nonylphenyl)amine, alkylphenyl-1-naphthylamine (octylphenyl) This includes phenylphenyl-l-naphthylamine and nt-dodecylphenyl-1-naphthylamine, 1-naphthylamines, arylnaphthylamines (phenyl-1-naphthylamine, phenyl-2-naphthylamine, N-hexylphenyl-2-naphthylamine, and N-octylphenyl-2-naphthylamine, etc.), phenylenediamines (N,N'-diisopropyl-p-phenylenediamine and N,N'-diphenyl-p-phenylenediamine, etc.), and phenothiazines (phenothiazines and 3,7-dioctylphenothiazines, etc.). 【0058】 Examples of phenolic antioxidants that can be conveniently used include the C7-C9 branched alkyl ester of 3,5-bis(1,1-dimethyl-ethyl)-4-hydroxybenzenepropanoic acid, 2-t-butylphenol, 2-t-butyl-4-methylphenol, 2-t-butyl-5-methylphenol, 2,4-di-t-butylphenol, 2,4-dimethyl-6-t-butylphenol, 2-t-butyl-4-methoxyphenol, 3-t-butyl-4-methoxyphenol, 2,5-di-t-butylhydroquinone, 2,6-di-t-butyl-4-alkylphenol (2,6-di-t-butylphenol, 2,6-di-t-butyl-4-methylphenol, and 2,6-di-t-butyl-4-ethylphenol, etc.), and 2,6-di-t-butyl-4-alkoxyphenol (2,6-di-t-butyl (e.g., -4-methoxyphenol and 2,6-di-t-butyl-4-ethoxyphenol), 3,5-di-t-butyl-4-hydroxybenzyl mercaptooctyl acetate, alkyl-3-(3,5-di-t-butyl-A-hydroxyphenyl)propionate (n-octadecyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, n-butyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, and 2'-ethylhexyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, etc.), 2,6-dt-butyl-A-dimethylamino-p-cresol, 2,2'-methylenebis(4-alkyl-6-t-butylphenol) (2,2'-methylenebis(4-methyl-6-t-butylphenol, and 2,2-methylenebis (e.g., 4-ethyl-6-t-butylphenol), bisphenol (4,4'-butyllidenebis(3-methyl-6-t-butylphenol, 4,4'-methylenebis(2,6-di-t-butylphenol), 4,4'-bis(2,6-di-t-butylphenol), 2,2-(di-p-hydroxyphenyl)propane, 2,2-bis(3,5-di-t-butyl-4-hydroxyphenyl)propane, 4,4'-cyclohexyllidenebis(2,6-t-butylphenol), hexamethylene glycol-bis [3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], triethylene glycol bis[3-(3-t-butyl-4-hydroxy-5-methylphenyl)propionate], 2,2'-thio~[diethyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], 3,9'-bis[1,1-dimethyl-2-[3-(3-t-butyl-4-hydroxy-5-methylphenyl)-propionyloxy]ethyl]2,4,8,10-tetraoxaspiro[5,5]unde Can, 4,4'-thiobis(3-methyl-6-t-butylphenol), and 2,21-thiobis(4,6-di-t-butylresorcinol), polyphenols (tetrakis[methylene-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate]methane, 1,1,3-tris(2-methyl-4-hydroxy-5-t-butylphenyl)butane, 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxybenzyl)benzene, bis-[3,3'-bis( Examples include 4'-hydroxy-3'-t-butylphenyl)butanoic acid glycol ester, 2-(3',5'-di-t-butyl-4-hydroxyphenyl)methyl-4-(2",4"-di-t-butyl-3"-hydroxyphenyl)methyl-6-t-butylphenol, and 2,6-bis(2'-hydroxy-3'-t-butyl-5'-methylbenzyl)-4-methylphenol, as well as pt-butylphenol-formaldehyde condensates and pt-butylphenol-acetaldehyde condensates. 【0059】 In another embodiment, the non-aqueous lubricant composition may contain one zinc dithiophosphate or a combination of two or more zinc dithiophosphates as an anti-wear additive, each zinc dithiophosphate being selected from zinc dialkyl-dithiophosphate, zinc diaryl-dithiophosphate, or zinc alkylaryl-dithiophosphate. The non-aqueous lubricant composition may generally contain zinc dithiophosphate in an amount ranging from about 0.4% to about 1.0% by weight based on the total weight of the non-aqueous lubricant composition. Additional or alternative known anti-wear additives may also be conveniently used in the non-aqueous lubricant composition. 【0060】 Surfactants that can be used in non-aqueous lubricant compositions include one or more salicylate and / or phenate and / or sulfonate surfactants. On the other hand, metal organic salts and inorganic base salts used as surfactants can contribute to the sulfated ash content of the non-aqueous lubricant composition, so in one embodiment, the amount of such additives is kept to a minimum. Furthermore, salicylate surfactants are preferred in order to maintain low sulfur levels. Therefore, in one embodiment, the non-aqueous lubricant composition may contain one or more salicylate surfactants. The surfactant may be used in an amount ranging from about 0.05% to about 12.5% ​​by weight, based on the total weight of the non-aqueous lubricant composition, in an amount ranging from about 1.0% to about 9.0% by weight in some embodiments, and in an amount ranging from about 2.0% to about 5.0% by weight in other embodiments. 【0061】 A second friction modifier (which may include one or more additional friction modifiers), including a metal-based friction modifier, may be used, and such a metal-based friction modifier may contain one or more organic molybdenum compounds (e.g., molybdenum dialkyldithiocarbamates, molybdenum dialkyldithiophosphates, molybdenum disulfides, tri-molybdenum cluster dialkyldithiocarbamates, sulfur-free molybdenum compounds, and the like), for example, a molybdenum dialkyldithiocarbamate friction modifier may exist. Many of these molybdenum compounds are well known and many are commercially available. The second friction modifiers that may coexist include organic fatty acids and derivatives of organic fatty acids, amides, imides, and other organometallic species (e.g., zinc compounds and boron compounds). These second friction modifiers may be added to the non-aqueous lubricant composition in an amount ranging from about 0.001% to about 5% by weight, based on the total weight of the non-aqueous lubricant composition. 【0062】 The non-aqueous lubricant compositions of this disclosure may further contain an ashless dispersant that can be mixed in an amount ranging from about 5% to about 15% by weight based on the total weight of the non-aqueous lubricant composition. 【0063】 Examples of ashless dispersants that can be used include polyalkenyl succinimide and polyalkenyl succinate esters. In one embodiment, the ashless dispersant includes borooxide succinimide. 【0064】 Examples of viscosity index improvers that can be conveniently used in the non-aqueous lubricant compositions of this disclosure include styrene-butadiene copolymers, styrene-isoprene radial copolymers, and polymethacrylate copolymers and ethylene-propylene copolymers. Such viscosity index improvers can be conveniently used in amounts ranging from about 1% to about 20% by weight, based on the total weight of the non-aqueous lubricant composition. 【0065】 Polymethacrylate can be conveniently used in the non-aqueous lubricant composition of the present invention as an effective pour point depressant. 【0066】 Furthermore, compounds such as alkenyl succinic acid or their ester portions, benzotriazole-based compounds, and thiodiazole-based compounds can be conveniently used as corrosion inhibitors in the non-aqueous lubricant compositions of this disclosure. 【0067】 Compounds such as polysiloxanes, dimethylpolycyclohexane, and polyacrylates can be conveniently used as defoaming agents in the non-aqueous lubricant compositions of this disclosure. 【0068】 Compounds that may be conveniently used in the non-aqueous lubricant compositions of this disclosure as seal fixatives or seal conformers include, for example, commercially available aromatic esters. 【0069】 As described above, the non-aqueous lubricant composition may contain any number of such additives. Therefore, in some embodiments, the final non-aqueous lubricant composition of the present disclosure will generally contain a combination of additives, including the reaction products of the present disclosure, together with other common additives, at a total concentration of about 0.1% to about 30% by weight (e.g., about 0.5% to about 10% by weight) based on the total weight of the non-aqueous lubricant composition. In other embodiments, the proportion of the reaction products and the combination of additives is about 1% to about 5% by weight based on the total weight of the non-aqueous lubricant composition. The oil concentrate of the reaction products and additives may contain about 30% to about 75% by weight of the additives based on the total weight of the non-aqueous lubricant composition. 【0070】 According to another embodiment, a non-aqueous lubricant composition is provided comprising A) a base oil in an amount of about 70% to about 99.9% by weight based on the total weight of the non-aqueous lubricant composition, B) a friction modifier disclosed herein, and C) one or more additional additives, wherein the total amount of B) and C) present in the composition is about 0.1% to about 30% by weight based on the total weight of the non-aqueous lubricant composition. 【0071】 In another embodiment, based on the total weight of the non-aqueous lubricant composition, the base oil may be present in an amount of about 90% to about 99.5% by weight, and the total amount of B) and C) is about 0.5% to about 10% by weight; in yet another embodiment, the base oil may be present in an amount of about 95% to about 99% by weight, and the total amount of B) and C) is about 1% to about 5% by weight. 【0072】 The friction modifiers containing the reaction products of the present disclosure may be added to a base oil directly on their own or in combination with one or more additives. Accordingly, in one embodiment, a friction-reducing additive package is provided, comprising the friction modifier containing the reaction products of the present disclosure and one or more additives. It is also possible to add the friction modifiers containing the reaction products of the present disclosure to a pre-formulated non-aqueous lubricant composition that already contains all or most of the other components and additives. 【0073】 Since friction modifiers containing the reaction products of this disclosure have been shown to dramatically improve friction reduction properties, the non-aqueous lubricant compositions of this disclosure can be used to improve the fuel efficiency of gas engines and diesel engines. Accordingly, a method for improving the friction reduction properties of a non-aqueous lubricant composition by adding a friction modifier containing the reaction products of this disclosure to a non-aqueous lubricant is also provided, and, correspondingly, a method for reducing friction between engine sliding parts by bringing the engine into contact with the non-aqueous lubricant composition of this disclosure is also provided. In some embodiments, the sliding parts may be piston rings / cylinder liners, crankshaft and connecting rod bearings, and valve mechanisms including cams and valve lifters. 【0074】 In yet another embodiment, a friction modifier (and one or more of the above additives of any choice) can be added to a petroleum distillation fuel (not limited to gasoline, diesel, and similar) to form a lubricating composition for lubricating sliding parts that are inaccessible to non-aqueous lubricant compositions. In such embodiments, the petroleum distillation fuel (such as gasoline fuel) may also include an anti-knock agent (such as methylcyclopentadienylmanganet tricarbonyl, tetramethyl lead, or tetraethyl lead) or other dispersants or surfactants (such as various substituted succinimides, amines, etc.). The lubricating composition can be easily prepared, for example, by dispersing the friction modifier, including the reaction products of the present disclosure, in a selected petroleum distillation fuel (for example, by adding the friction modifier to the petroleum distillate and stirring the resulting solution by agitation or other means to uniformly disperse the reaction products in the composition). Any conventional fuel mixing method can be used in this regard. The amount of friction modifier containing the reaction product of this disclosure dispersed in the fuel may be about 0.1% to about 30% by weight (e.g., more than about 0.5% to about 10% by weight) based on the total weight of the lubricant composition. In other embodiments, the total amount of friction modifier present is about 1% to about 5% by weight based on the total weight of the lubricant composition. 【0075】 This disclosure will be further illustrated hereby with reference to the following non-limiting examples. [Examples] 【0076】 Example 1 Two reaction products (FM-A and FM-B) were prepared by reacting a fat amine with glycidol. This reaction was carried out by adding glycidol to the fat amine at 150°C, followed by a 4-hour immersion time. These two reaction products (prepared from the fat amine-glycidol ring-opening reaction) are listed in the table below. [Table 1] 【0077】 Next, the alkylalkoxylated monoamine is reacted with glycidol to produce two additional The reaction products (FM-C and FM-D) were prepared. The structure of the alkylalkoxylated monoamine is given by formula [ka] It has the following characteristics: In the formula, Z is C 12 -C 14 The alkyl group is Z', the methyl group is Z', and e is an integer with an average value of approximately 2 to 5. This reaction was carried out by adding glycidol to the alkylalkoxylated monoamine at 150°C, followed by a 4-hour immersion time. The two reaction products (prepared from the alkylalkoxylated monoamine glycidol ring-opening reaction) are listed in the table below. [Table 2] 【0078】 Next, the coefficient of friction of commercially available oil and commercially available oil containing an additional 0.5% of the above reaction products was determined at 100°C and 130°C using a mini traction machine equipped with a 3 / 4-inch ball on a flat disc. The load was 36N (contact pressure 1GPa), and the rotation speed was 0.01m / s to 2m / s. The results at 130°C are shown in Tables 1 and 2 below. [Table 3] [Table 4] 【0079】 The results in Tables 1 and 2 demonstrate that the friction modifiers of the present invention (FM-A, B, C, and D), including the reaction products, can significantly reduce the coefficient of friction of Mobil 1 5W-30 oil and Pennzoil 0W-20 oil. To illustrate these results in more detail, Figures 1 and 2 show the full range of the coefficients of friction for FM-A and B. 【0080】 Because the reaction products of the present invention contain multiple OH groups in their polar heads, they can be strongly adsorbed onto surfaces. The linear structure of the hydrophobic tails in FM-A, B, C, and D allows the reaction products to align well on surfaces due to the strong van der Waals forces generated between their tails. This unique molecular structure makes these reaction products excellent friction modifiers in oil.

Claims

[Claim 1] Base oil and (i) formula 【Chemistry 1】 It is an alkylalkoxylated amine having the following properties: In the formula, Z is C 1 -C 30 A non-aqueous lubricant composition comprising a friction modifier comprising a reaction product of an alkylalkoxylated amine, which is an alkyl group, alicyclic group, or aryl group, where each Z' is independently hydrogen, methyl, or ethyl, and e is an integer from 1 to 100, and (ii) glycidol. [Claim 2] The mixture further contains a second organic amine, wherein the second organic amine is N(R) 1 ) 3 It is an alkylamine having the formula, where each R 1 However, hydrogen or C 1 -C 50 It is an alkyl group, however, at least one R 1 The non-aqueous lubricant composition according to claim 1, wherein the condition is that the is hydrogen. [Claim 3] The non-aqueous lubricant composition according to claim 1, further comprising a second organic amine, wherein the second organic amine is an alicyclic amine selected from cyclopentylamine, cyclohexylamine, cycloheptylamine, cyclododecylamine, 4-methylcyclohexylamine, N,N-dimethylcyclohexylamine, hexamethyleneimine, piperidine, and isophoronediamine. 【Claim 4】 Further comprising a second organic amine, wherein the second organic amine is C 1 -C 20 The non-aqueous lubricant composition according to claim 1, which is an arylamine substituted with an alkyl group. [Claim 5] Z is C 1 -C 30 The non-aqueous lubricant composition according to claim 1, wherein the alkyl group is an alkyl group. [Claim 6] The non-aqueous lubricant composition according to claim 1, wherein the friction modifier is present in an amount ranging from 0.1% by weight to 1.5% by weight based on the total weight of the non-aqueous lubricant composition. [Claim 7] The non-aqueous lubricant composition according to claim 1, wherein the base oil is a synthetic oil. [Claim 8] The non-aqueous lubricant composition according to claim 1, wherein the base oil is mineral oil. [Claim 9] A method for reducing friction between sliding parts of an engine by bringing the engine into contact with the non-aqueous lubricant composition described in claim 1. [Claim 10] A friction-reducing additive package comprising the friction modifier described in claim 1, and one or more additives selected from antioxidants, wear-resistant additives, surfactants, dispersants, second friction modifiers, viscosity index improvers, pour point depressants, corrosion inhibitors, defoamers, seal fixatives, seal compatibility agents, and mixtures thereof. [Claim 11] Base oil and, formula: 【Chemistry 2】 A non-aqueous lubricant composition comprising a friction modifier containing a compound having, In the formula, R is 【Transformation 3】 It is an alkylalkoxylate group having, The non-aqueous lubricant composition wherein Z is an alkyl group, an alicyclic group, or an aryl group, Z' is independently hydrogen, methyl, or ethyl, and e is an integer from 1 to 100. [Claim 12] R is C 1 -C 25 The alkyl group having formulas (5) to (8) as defined in claim 11 The non-aqueous lubricant composition according to claim 11, further comprising a second friction modifier compound. [Claim 13] R is a phenyl group, or C 1 -C 20 The non-aqueous lubricant composition according to claim 11, further comprising a second friction modifier compound having formulas (5) to (8) as defined in claim 11, which is a phenyl group substituted with an alkyl group. [Claim 14] R is an alkylalkoxylate group, and Z is C 1 -C 20 The non-aqueous lubricant composition according to claim 11, further comprising a second friction modifier compound having formulas (5) to (8) defined in claim 11, wherein each Z' is an alkyl group, and each Z' is independently hydrogen or methyl, and e is an integer from 1 to 25. [Claim 15] The non-aqueous lubricant composition according to claim 11, further comprising a second friction modifier compound, wherein the second friction modifier compound comprises at least one of 2,3-dihydroxypropylamine, 1,3-dihydroxypropylamine, bis(2,3-dihydroxypropyl)amine, bis(1,3-dihydroxypropyl)amine, or (2,3-dihydroxypropyl)(1,3-dihydroxypropyl)amine.

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