Grease thickener

Abstract

The present disclosure provides a polyamide grease thickener having a structure according to formula I: (MCA-DA-)(PCA-DA) y -PCA-(DA-PCA) y (-DA-MCA)(I). In formula I, in each occurrence, PCA is independently a reacted polycarboxylate, in each occurrence, MCA is independently a reacted monocarboxylate, in each occurrence, DA is independently a reacted n-alkyldiamine, and y is an integer other than 0 or zero. Additionally, in formula I, the weight average molecular weight of the polyamide grease thickener ranges from about 450 g / mol to about 2600 g / mol. Additionally, in formula I, the structure contains at least four amide bonds, and at least two internal aromatic moieties are disubstituted in the para position.

Description

Technical Field

[0001] (Cross - reference to related applications) This application claims the benefit of priority to U.S. Provisional Patent Application No. 63 / 351,582, entitled "GREASE THICKENING AGENT", filed on June 13, 2022, the disclosure of which is hereby incorporated by reference in its entirety. This application further claims the benefit of priority to U.S. Provisional Patent Application No. 63 / 423,815, entitled "GREASE THICKENING AGENT", filed on November 9, 2022, the disclosure of which is hereby incorporated by reference in its entirety. This application further claims the benefit of priority to U.S. Provisional Patent Application No. 63 / 463,576, entitled "GREASE THICKENING AGENT", filed on May 3, 2023, the disclosure of which is hereby incorporated by reference in its entirety.

Background Art

[0002] Grease compositions provide lubrication for various articles. While it is important for grease compositions to contain suitable lubricating oils and base oils, a grease thickener is required to provide mechanical properties to the grease composition.

Summary of the Invention

[0003] The present disclosure provides a polyamide grease thickener having a structure according to Formula I: (MCA - DA -)(PCA - DA) y -PCA-(DA - PCA) y (-DA - MCA)(I) In Formula I, in each occurrence, PCA is, independently, a reacted polycarboxylate, in each occurrence, MCA is, independently, a reacted monocarboxylate, in each occurrence, DA is, independently, a reacted diamine, and y is an integer other than 0 or zero. Additionally, in Formula I, the weight average molecular weight of the polyamide grease thickener ranges from about 450 g / mol to about 3500 g / mol. Additionally, in Formula I, the structure contains at least 4 amide bonds and at least 2 internal aromatic moieties are disubstituted in the para position.

[0004] Surprisingly and unexpectedly, according to various aspects of the present disclosure, the grease thickening composition can function at least substantially equivalently to the corresponding grease thickener containing lithium, polyurea, or both. Thus, it is possible to formulate a grease composition that is substantially free of lithium, polyurea, or both.

Brief Description of the Drawings

[0005] The drawings generally illustrate, by way of example and not limitation, various aspects of the present disclosure.

[0006]

Figure 1

Modes for Carrying Out the Invention

[0007] Reference is now made in detail to certain embodiments of the disclosed subject matter. It will be understood that the disclosed subject matter is described in conjunction with the recited claims, but the exemplified subject matter is not intended to limit the disclosed subject matter to the recited claims.

[0008] Throughout this document, values expressed in a range format are to be interpreted in a flexible manner such that they include not only the numerical values explicitly listed as the limits of the range, but also all individual numerical values or sub-ranges subsumed within that range as if each numerical value and sub-range were explicitly listed. For example, a range of "about 0.1% to about 5%" or "about 0.1% to 5%" is to be interpreted as including not only about 0.1% to about 5%, but also individual values (e.g., 1%, 2%, 3%, and 4%) and sub-ranges (e.g., 0.1% to 0.5%, 1.1% to 2.2%, 3.3% to 4.4%) within the indicated range. A description of "about X to Y" has the same meaning as "about X to about Y" unless otherwise indicated. Similarly, a description of "about X, Y, or about Z" has the same meaning as "about X, about Y, or about Z" unless otherwise indicated.

[0009] In this document, the terms "a", "an", or "the" are used to include one or more than one unless the context clearly dictates otherwise. The term "or" is used to refer to a non-exclusive "or" unless otherwise indicated. A description of "at least one of A and B" or "at least one of A or B" has the same meaning as "A, B, or A and B". Additionally, any syntax or terminology used in this specification and not otherwise defined is for descriptive purposes only and is not limiting. Any use of section headings is intended to assist in reading the document and is not to be construed as limiting. Information related to a section heading may occur within or outside of that particular section.

[0010] In the methods described herein, acts can be performed in any order, without departing from the principles of the invention, unless a temporal or operational order is explicitly recited. Further, acts can be performed simultaneously, unless explicitly specified otherwise in the literal language of the claims. For example, the claimed act of doing X and the claimed act of doing Y can be performed simultaneously in a single operation, and the resulting process is within the literal scope of the claimed process.

[0011] As used herein, the term "about" can allow for a degree of variation in a value or range, for example, within 10%, 5%, or 1% of the limits of the recited value or recited range, and includes the recited exact value or range.

[0012] As used herein, the term "substantially" refers to a majority or almost all, such as at least about 50%, 60%, 70%, 80%, 90%, 95%, 96%, 97%, 98%, 99%, 99.5%, 99.9%, 99.99%, or at least about 99.999% or more, or 100%. As used herein, the term "substantially free of" can mean that the amount of the material present is absent or present in a negligible amount such that it does not affect the material properties of the composition containing the material, and as a result, about 0 wt% to about 5 wt% of the composition is the material, or about 0 wt% to about 1 wt%, or about 5 wt% or less, or about 4.5 wt%, 4, 3.5, 3, 2.5, 2, 1.5, 1, 0.9, 0.8, 0.7, 0.6, 0.5, 0.4, 0.3, 0.2, 0.1, less than 0.01, or equal thereto, or about 0.001 wt% or less, or about 0 wt%.

[0013] As used herein, the term "organic group" refers to any carbon-containing functional group. Examples include oxygen-containing groups such as alkoxy, aryloxy, aralkyloxy, oxo (carbonyl) groups, carboxyl groups including carboxylic acids, carboxylates, and carboxylate esters, sulfur-containing groups such as alkyl and aryl sulfide groups, and other heteroatom-containing groups. Non-limiting examples of organic groups include OR, OOR, OC(O)N(R)2, CN, CF3, OCF3, R, C(O), methylenedioxy, ethylenedioxy, N(R)2, SR, SOR, SO2R, SO2N(R)2, SO3R, C(O)R, C(O)C(O)R, C(O)CH2C(O)R, C(S)R, C(O)OR, OC(O)R, C(O)N(R)2, OC(O)N(R)2, C(S)N(R)2, CH2) 0-2 N(R)C(O)R, (CH2) 0-2 N(R)N(R)2, N(R)N(R)C(O)R, N(R)N(R)C(O)OR, N(R)N(R)CON(R)2, N(R)SO2R, N(R)SO2N(R)2, N(R)C(O)OR, N(R)C(O)R, N(R)C(S)R, N(R)C(O)N(R)2, N(R)C(S)N(R)2, N(COR)COR, N(OR)R, C(=NH)N(R)2, C(O)N(OR)R, C(=NOR)R, and substituted or unsubstituted (C1-C 100 )hydrocarbylene, where R can be hydrogen (in examples that include other carbon atoms) or a carbon-based moiety, and the carbon-based moiety can be substituted or unsubstituted.

[0014] As used herein in connection with a molecule or organic group defined herein, the term "substituted" refers to a state in which one or more hydrogen atoms contained therein are replaced by one or more non-hydrogen atoms. As used herein, the term "functional group" or "substituent" refers to a group that can be substituted or is substituted on a molecule or an organic group. Examples of substituents or functional groups include halogen (e.g., F, Cl, Br, and I), hydroxy group, alkoxy group, aryloxy group, aralkyloxy group, oxo (carbonyl) group, carboxyl group including carboxylic acid, carboxylate, and oxygen atoms in groups such as carboxylic acid ester, thiol group, alkyl and aryl sulfide groups, sulfoxide group, sulfone group, sulfonyl group, and sulfur atoms in groups such as sulfonamide group, nitrogen atoms in groups such as amine, hydroxyamine, nitrile, nitro group, N-oxide, hydrazide, azide, and enamine, and other heteroatoms in various other groups, but are not limited thereto. Non-limiting examples of substituents that can be attached to a substituted carbon (or other) atom include F, Cl, Br, I, OR, OC(O)N(R)2, CN, NO, NO2, ONO2, azide, CF3, OCF3, R, O (oxo), S (thiono), C(O), S(O), methylenedioxy, ethylenedioxy, N(R)2, SR, SOR, SO2R, SO2N(R)2, SO3R, C(O)R, C(O)C(O)R, C(O)CH2C(O)R, C(S)R, C(O)OR, OC(O)R, C(O)N(R)2, OC(O)N(R)2, C(S)N(R)2, CH2) 0-2 N(R)C(O)R, (CH2) 0-2 N(R)N(R)2, N(R)N(R)C(O)R, N(R)N(R)C(O)OR, N(R)N(R)CON(R)2, N(R)SO2R, N(R)SO2N(R)2, N(R)C(O)OR, N(R)C(O)R, N(R)C(S)R, N(R)C(O)N(R)2, N(R)C(S)N(R)2, N(COR)COR, N(OR)R, C(=NH)N(R)2, C(O)N(OR)R, and C(=NOR)R, wherein R can be hydrogen or a carbon-based moiety. For example, R is hydrogen, (C1-C 100)It can be hydrocarbyl, alkyl, acyl, cycloalkyl, aryl, aralkyl, heterocyclyl, heteroaryl, or heteroarylalkyl, or two R groups bonded to a nitrogen atom or adjacent nitrogen atoms can together with one or more nitrogen atoms form a heterocyclyl.

[0015] As used herein, the term "alkyl" refers to straight-chain and branched alkyl groups and cycloalkyl groups having from 1 to 40 carbon atoms, from 1 to about 20 carbon atoms, from 1 to 12 carbon atoms, or in some embodiments, from 1 to 8 carbon atoms. Examples of straight-chain alkyl groups include those having from 1 to 8 carbon atoms such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, and n-octyl groups. Examples of branched alkyl groups include, but are not limited to, isopropyl, iso-butyl, sec-butyl, t-butyl, neopentyl, isopentyl, and 2,2-dimethylpropyl groups. As used herein, the term "alkyl" encompasses n-alkyl, isoalkyl, and anteisoalkyl groups, as well as other branched-chain forms of alkyl. Representative substituted alkyl groups can be substituted one or more times with any of the groups listed herein, for example, amino, hydroxy, cyano, carboxy, nitro, thio, alkoxy, and halogen groups.

[0016] As used herein, the term "alkenyl" refers to straight-chain, branched-chain, and cyclic alkyl groups as defined herein, except that at least one double bond is present between two carbon atoms. Thus, alkenyl groups have from 2 to 40 carbon atoms, or from 2 to about 20 carbon atoms, or from 2 to 12 carbon atoms, or in some embodiments, from 2 to 8 carbon atoms. Examples include, but are not limited to, vinyl, -CH=CH(CH3), -CH=C(CH3)2, -C(CH3)=CH2, -C(CH3)=CH(CH3), -C(CH2CH3)=CH2, cyclohexenyl, cyclopentenyl, cyclohexadienyl, butadienyl, pentadienyl, and hexadienyl.

[0017] As used herein, the term "alkynyl" refers to straight-chain and branched-chain alkyl groups, except that at least one triple bond is present between two carbon atoms. Thus, an alkynyl group has 2 to 40 carbon atoms, 2 to about 20 carbon atoms, or 2 to 12 carbon atoms, or in some embodiments, 2 to 8 carbon atoms. Examples include, but are not limited to, -CH, -C(CH3), -C(CH2CH3), -CH2CH, -CH2C(CH3), and -CH2C(CH2CH3).

[0018] As used herein, the term "acyl" refers to a group containing a carbonyl moiety, wherein the group is bonded through the carbonyl carbon atom. The carbonyl carbon atom is bonded to a hydrogen forming a "formyl" group or to another carbon atom that can be part of an alkyl, aryl, aralkylcycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, heteroaryl, heteroarylalkyl group, etc. An acyl group can contain 0 to about 12, 0 to about 20, or 0 to about 40 additional carbon atoms bonded to the carbonyl group. An acyl group can contain a double bond or a triple bond within the meaning herein. An acryloyl group is an example of an acyl group. An acyl group can also contain a heteroatom within the meaning herein. A nicotinoyl group (pyridyl-3-carbonyl) is an example of an acyl group within the meaning herein. Other examples include acetyl, benzoyl, phenylacetyl, pyridylacetyl, cinnamoyl, and acryloyl groups. When a group containing a carbon atom bonded to the carbonyl carbon atom contains a halogen, the group is called a "haloacyl" group. An example is the trifluoroacetyl group.

[0019] As used herein, the term "cycloalkyl" refers to a cyclic alkyl group such as, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups. In some embodiments, the cycloalkyl group may have from 3 to about 8 to 12 ring members, while in other embodiments, the number of ring carbon atoms ranges from 3 to 4, 5, 6, or 7. The cycloalkyl group further includes polycyclic cycloalkyl groups such as, but not limited to, norbornyl, adamantyl, bornyl, camphyl, isocampphyl, and carenyl groups, and fused rings such as, but not limited to, decalinyl. The cycloalkyl group also includes rings substituted with a straight-chain or branched-chain alkyl group as defined herein. Representative substituted cycloalkyl groups can be mono-substituted or substituted more than once, for example, can be substituted with amino, hydroxy, cyano, carboxy, nitro, thio, alkoxy, and halogen groups, 2,2-, 2,3-, 2,4-, 2,5-, or 2,6-disubstituted cyclohexyl groups, or mono-, di-, or trisubstituted norbornyl groups or cycloheptyl groups, etc., but not limited thereto. The term "cycloalkenyl" indicates a cyclic alkenyl group, alone or in combination.

[0020] As used herein, the term "aryl" refers to a cyclic aromatic hydrocarbon group that does not contain a heteroatom in the ring. Thus, aryl groups include, but are not limited to, phenyl, azulenyl, heptalenyl, biphenyl, indacenyl, fluorenyl, phenanthrenyl, triphenylenyl, pyrenyl, naphthacenyl, chrysenyl, biphenyleneyl, anthracenyl, and naphthyl groups. In some embodiments, the aryl group contains from about 6 to about 14 carbons in the ring portion of the group. The aryl group can be unsubstituted or substituted as defined herein. Representative substituted aryl groups can be mono-substituted or substituted more than once, a phenyl group substituted at any one or more of the 2, 3, 4, 5, or 6 positions of the phenyl ring, or a naphthyl group substituted at any one or more of the 2 to 8 positions thereof, etc., but not limited thereto.

[0021] As used herein, the term "aralkyl" refers to an alkyl group as defined herein in which a hydrogen or carbon bond of the alkyl group is replaced by a bond to an aryl group as defined herein. Representative aralkyl groups include benzyl and phenylethyl groups, and fused (cycloalkylaryl)alkyl groups such as 4-ethyl-indanyl. An aralkenyl group is an alkenyl group as defined herein in which a hydrogen or carbon bond of the alkyl group is replaced by a bond to an aryl group as defined herein.

[0022] As used herein, the term "heterocyclyl" refers to aromatic and non-aromatic ring compounds containing three or more ring members, one or more of which are heteroatoms such as, but not limited to, N, O, and S.

[0023] As used herein, the term "heteroaryl" refers to an aromatic ring compound containing five or more ring members, one or more of which are heteroatoms such as, but not limited to, N, O, and S. For example, a heteroaryl ring can have 5 to about 8 to 12 ring members. A heteroaryl group is a variety of heterocyclyl groups having an aromatic electronic structure.

[0024] As used herein, the term "heterocyclylalkyl" refers to an alkyl group as defined herein in which a hydrogen or carbon bond of the alkyl group is replaced by a bond to a heterocyclyl group as defined herein. Representative heterocyclylalkyl groups include, but are not limited to, furan-2-ylmethyl, furan-3-ylmethyl, pyridin-3-ylmethyl, tetrahydrofuran-2-ylethyl, and indol-2-ylpropyl.

[0025] As used herein, the term "heteroarylalkyl" refers to an alkyl group as defined herein, wherein a hydrogen or carbon bond of the alkyl group is replaced by a bond to a heteroaryl group as defined herein.

[0026] As used herein, the term "alkoxy" refers to an oxygen atom bonded to an alkyl group containing a cycloalkyl group as defined herein. Examples of linear alkoxy groups include, but are not limited to, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, etc. Examples of branched alkoxy include, but are not limited to, isopropoxy, sec-butoxy, tert-butoxy, isopentyloxy, isohexyloxy, etc. Examples of cyclic alkoxy include, but are not limited to, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, etc. The alkoxy group can contain from about 1 to about 12, from about 1 to about 20, or from about 1 to about 40 carbon atoms bonded to the oxygen atom, can further contain double or triple bonds, and can also contain heteroatoms. For example, an allyloxy group or a methoxyethoxy group is also an alkoxy group within the scope of the meaning herein, similar to a methylenedioxy group in the context where two adjacent atoms of the structure are substituted.

[0027] As used herein, the term "amine" refers to, for example, primary, secondary, and tertiary amines having the formula N(group)3, wherein each group can independently be H or non-H such as alkyl, aryl, etc. Amines include, but are not limited to, R-NH2, such as alkylamine, arylamine, alkylarylamine; R2NH, wherein each R is independently selected, dialkylamine, diarylamine, aralkylamine, heterocyclylamine, etc.; and R3N, wherein each R is independently selected, trialkylamine, dialkylarylamine, alkyldiarylamine, triarylamine, etc. The term "amine" also includes ammonium ions as used herein.

[0028] As used herein, the term "amino group" refers to substituents of the form -NH2, -NHR, -NR2, -NR3 (each R being independently selected), and non-protonatable -NR3 + excluding each protonated form. Thus, any compound substituted with an amino group can be regarded as an amine. The "amino group" within the scope of meaning herein can be a primary, secondary, tertiary, or quaternary amino group. The "alkylamino" group includes monoalkylamino, dialkylamino, and trialkylamino groups. + The terms "halo", "halogen", or "halide" group, as used herein, mean a fluorine, chlorine, bromine, or iodine atom, either by itself or as part of another substituent, unless otherwise specified.

[0029] The term "haloalkyl" group, as used herein, includes monohaloalkyl groups, polyhaloalkyl groups where all halo atoms may be the same or different, and perhaloalkyl groups where all hydrogen atoms are replaced by halogen atoms such as fluorine. Examples of haloalkyl include trifluoromethyl, 1,1-dichloroethyl, 1,2-dichloroethyl, 1,3-dibromo-3,3-difluoropropyl, perfluorobutyl, and the like.

[0030] The term "hydrocarbon" or "hydrocarbyl" as used herein refers to a molecule or functional group containing carbon and hydrogen atoms. This term can also refer to a molecule or functional group that usually contains both carbon and hydrogen atoms, but where all hydrogen atoms are replaced by other functional groups. The term "hydrocarbyl" refers to a functional group derived from a straight-chain, branched, or cyclic hydrocarbon and can be alkyl, alkenyl, alkynyl, aryl, cycloalkyl, acyl, or any combination thereof. A hydrocarbyl group is (C

[0031] ~C a ~C b) It can be represented as a hydrocarbyl, where a and b are integers, meaning it can have any number of carbon atoms from a to b. For example, (C1-C4) hydrocarbyl means that the hydrocarbyl group can be methyl (C1), ethyl (C2), propyl (C3), or butyl (C4), and (C0-C b ) Hydrocarbyl, in certain embodiments, means that there is no hydrocarbyl group. A hydrocarbylene group is a diradical hydrocarbon, for example, a hydrocarbon that is bonded at two locations.

[0032] As used herein, the term "weight-average molecular weight" refers to ΣM i 2 n i / ΣM i n i equal to M w where n i is the number of molecules of molecular weight M i . In various examples, the weight-average molecular weight can be determined using light scattering, small-angle neutron scattering, X-ray scattering, and sedimentation velocity.

[0033] The polymers described herein can be terminated in any suitable manner. In some embodiments, the polymer is interrupted by 0, 1, 2, or 3 groups independently selected from -O-, substituted or unsubstituted -NH-, and -S-, poly(substituted or unsubstituted (C1-C 20 ) hydrocarbyloxy), and poly(substituted or unsubstituted (C1-C 20 ) hydrocarbylamino), and can be terminated with end groups independently selected from a suitable polymerization initiator, -H, -OH, substituted or unsubstituted (C1-C 20 ) hydrocarbyl (e.g., (C1-C 10 ) alkyl or (C6-C 20 ) aryl).

[0034] The origin of any reactant, feedstock, and / or material can be from any available source. By way of non-limiting example, such sources can include natural products, synthetic products, petrochemicals, bio-renewables, recycled materials, or mixtures thereof.

[0035] Various aspects of the present disclosure relate to grease thickeners. The grease thickeners are characterized as polyamide grease thickeners. Successful grease thickeners have been found to result in a grease composition having a dropping point above 200 °C, 220, 240, 260, or 280 °C and having an NLGI grade of 2 or higher. The structural features of the grease thickeners that have been found to be useful in achieving these properties include that any aliphatic moiety in the monomers located within the grease thickener molecule is n-alkyl (linear), and additionally, the grease thickener should contain at least two para-substituted aromatic moieties, the grease thickener should have a molecular weight in the range of 450 g / mol to 3500 g / mol, and the grease thickener should contain at least four amide bonds. These structural features have been found to achieve desirable physical properties when the grease thickener is incorporated into the grease composition at a concentration of about 10 wt% to 20 wt%, in the range of about 10 wt% to about 15 wt%, about 10 wt%, 11, 12, 13, 14, 15, 16, 17, 18, 19, or less than, equal to, or greater than about 20 wt%.

[0036] Various examples of grease thickeners are described herein. Some of the described structures may not have each of the aforementioned desirable structural features. However, some grease thickeners that include at least some of the aforementioned desirable features may provide a grease thickener that functions well enough. Additionally, in various aspects, it may be desirable for a grease composition to include a mixture of grease thickening components. In such a mixture, at least one grease thickener can include all of the aforementioned desirable structural features. Additionally, the mixture can include another grease thickening agent that includes a number of structural features less than all of the aforementioned structural features, or even any of the structural features. However, the mixture itself can still provide the desirable properties in the grease composition in which it is incorporated.

[0037] The polyamide grease thickener has the structure according to formula VIII: (MCA-DA-(ZZ) y -) x PCA(VIII) and can have the structure according to. In formula I, in each occurrence, ZZ is

Chem.

Chem.

[0038] The polyamide grease thickener has the formula I: (MCA-DA-)(PCA-DA) y -PCA-(DA-PCA) y (-DA-MCA)(I) and can have a structure according to. In a further example, the polyamide grease thickener has the formula II: ((MCA-DA-)(PCA-DA) y -) n PCA(II) and can have a structure according to. In formula II, n is in the range of 2 to 4. In a further example, the polyamide grease thickener has the formula III: (MCA-DA)-PCA-(DA-MCA)(III) and has a structure according to.

[0039] The reacted polycarboxylate can be a polycarboxylic acid, polycarboxylic acid ester, polycarboxylic acid chloride, or anhydride. In each occurrence, the PCA can independently contain 3 to 50 carbon atoms, 6 to 10 carbon atoms, or 6, 8, or 9 carbon atoms. For example, in each occurrence, the PCA has the following formula: Formula (X):

Chem.

Chem.

Chem.

[0040] In each occurrence, R 1 and R 2 are independently a bond or a substituted or unsubstituted (C1 - C 20 ) hydrocarbyl, and in each occurrence, R 6 is selected from -OH, -Cl, -O - , or a substituted or unsubstituted -O-(C1 - C 20 ) hydrocarbyl. In each occurrence, the substituted or unsubstituted (C1 - C 20 ) hydrocarbyl is independently a substituted or unsubstituted (C1 - C 20 ) alkyl, substituted or unsubstituted (C3 - C 20 ) cycloalkyl, substituted or unsubstituted (C2 - C 20 ) alkenyl, substituted or unsubstituted (C2 - C 20 ) alkynyl, substituted or unsubstituted (C1 - C 20 ) acyl, substituted or unsubstituted (C4 - C 20 ) aryl, and substituted or unsubstituted (C2 - C 20 ) alkoxy. In some examples, in each occurrence, the PCA has the same chemical structure. Alternatively, at least two occurrences of the PCA can have different chemical structures.

[0041] As a specific example, in each occurrence, PCA independently includes reacted adipic acid, reacted purified terephthalic acid, reacted isophthalic acid, reacted phthalic anhydride, reacted naphthoic acid, reacted mellitic acid, reacted mellitic anhydride, reacted naphthalenetetracarboxylic dianhydride, reacted citric acid, reacted ester, reacted acid chloride, reacted dianhydride, or reacted ethylenediaminetetraacetic acid. PCA can contain three carboxylic acid groups or two carboxylic acid groups. A more preferred structure of the grease thickener composition is the structure of Formula II or III. That is, the structure of Formula II or III makes it easier to form a grease thickener having a combination of the desirable structural features described above herein. In a preferred embodiment, the grease thickener component has at least four amide bonds.

[0042] In each occurrence, MCA can include a reacted ester, a reacted acid chloride, or a reacted anhydride. For example, in each occurrence, MCA can include a reacted monocarboxylate, and the monocarboxylate has the formula (IV):

Chemical formula

[0043] As a further example, in each occurrence, the MCA can include the reacted monocarboxylate. The monocarboxylate can have the formula: Formula (V):

Chemical formula

Chemical formula

[0044] Although not intended to be bound by any theory, it is believed that a grease thickener in which the MCA contains an aromatic group, an alicyclic group, or an aliphatic group provides the best performance with respect to the grease thickener in the grease composition. Further, when the first MCA contains an aromatic group and the second MCA contains an aliphatic group or an alicyclic group, it is believed that excellent performance can be achieved. In particular, the second MCA containing an aliphatic chain having 6 to 8 carbon atoms is believed to provide excellent performance. The hydrophobicity of the aliphatic group is believed to help provide compatibility with the grease. Also, R 3 and R 4 are not bonded, these are preferably n-(C1-C 20 ) alkylene because it is more easily possible to form a grease thickener having the desired combination of structural features described above in this specification, and is thus considered better.

[0045] As shown, the reaction between each MCA group and the DA group results in a grease thickener having a terminal amide group. Although not intended to be bound by any theory, the terminal amide group is believed to provide several advantages. For example, the amide group gives the grease thickener reactivity at the level of other polyamides such as nylon-6,6, which means that the grease thickener is relatively inert to reaction with other components of the grease composition. Thus, the grease thickener can remain in the grease composition in an unreacted form. Further, the amide bond is less susceptible to hydrolysis. Thus, the grease thickener can withstand a certain level of water that may be present (intentionally or unintentionally) in the grease composition. Additionally, the grease thickener can be synthesized in the presence of water. These advantages are particularly evident compared to grease thickeners having terminal ester groups. Terminal ester groups are likely to react with other grease components or undergo hydrolysis, either of which can reduce the effectiveness of the grease thickener.

[0046] In each occurrence, DA is independently of the formula (VII):

Chemical formula

[0047] In certain examples, in each occurrence, DA is a reacted diamine independently selected from reacted hexamethylenediamine, reacted propanediamine, reacted butanediamine, reacted pentanediamine, reacted nonanediamine, reacted isononanediamine, reacted 2-methylpentamethylenediamine, reacted ethylenediamine, reacted isophoronediamine, reacted m-xylylenediamine, and reacted m-phenylenediamine. In some examples, in each occurrence, DA is reacted hexamethylenediamine. In a more specific example, n--(C1-C 20) It has been found that an internal aliphatic group which is an alkylene gives rise to a grease thickener having a desirable dropping point and NLGI characteristics. Typically, DA does not contain a branched structure. This is because diamines having a branched structure tend to overly soften the grease composition containing the grease thickener, and then overly lower the melting point of the grease composition. In some examples, DA can be selected from reacted hexamethylenediamine, reacted propanediamine, reacted butanediamine, reacted pentanediamine, or reacted nonanediamine.

[0048] The grease thickener can exist as a distribution. In the distribution, the weight average molecular weight of the grease thickener ranges from about 400 g / mol to about 10,000 g / mol, from about 1100 g / mol to about 8,000 g / mol, from about 1200 g / mol to about 4000 g / mol, 400 g / mol, 450, 500, 550, 600, 650, 700, 750, 800, 850, 900, 950, 1000, 1050, 1100, 1150, 1200, 1250, 1300, 1350, 1400, 1450, 1500, 2000, 2500, 3000, 3500, 4000, 4500, 5000, 5500, 6000, 6500, 7000, 7500, 8000, 8500, 9000, 9500, or less than, equal to, or greater than about 10,000 g / mol. Maintaining the weight average molecular weight within this range can help the polyamide grease polymer be classified as a polymer for regulatory purposes under 40 CFR 723.250(b). In certain examples, a weight average molecular weight in the range of about 450 g / mol to about 3500 g / mol or about 500 g / mol to about 2500 g / mol has been found to result in a grease thickener having particularly advantageous properties (e.g., dropping point and NLGI value). Additionally, it has been found that if the weight average molecular weight of the grease thickening component is too large, it is not compatible with the base oil of the grease composition. Incompatibility is established when the grease composition is not homogeneous. The grease composition is considered to be homogeneous when discrete particles are observed when examined under a 200-fold microscope.

[0049] Generally, when the polyamide grease thickener is completely linear (e.g., without including alicyclic, aromatic, etc.), it has been found that the resulting grease has insufficient penetration measurement, meaning the grease is too soft. Examples of linear polyamides can be found in GB774085). However, it has been found that at least some linearity is desirable since all aromatic polyamides show poor compatibility (e.g., low dropping point) when incorporated into the grease composition. Additionally, when the weight average molecular weight of the polyamide grease thickener is too large, it has been found that the compatibility of the grease composition deteriorates (e.g., the homogeneity is lost).

[0050] Specific examples of suitable grease thickeners that can be used alone or as a mixture of grease thickeners include those shown in Table 1 herein. Among these grease thickeners listed in Table 1, the structures of Formulas XII, XI, X, and XIII include the aforementioned beneficial structures and show good performance in the grease composition. The data includes the dropping points P0 and P 60 values when available for each grease thickener incorporated into the grease composition. [Table 1-1] [Table 1-2] [Table 1-3] [Table 1-4] [Table 1-5] [Table 1-6] [Table 1-7]

[0051] Polyamide grease thickeners can be components of grease compositions. A grease composition is generally understood to refer to a solid or semi-solid lubricant formed as a dispersion of a thickener in a liquid lubricant. A grease composition includes a base oil (or lubricating oil), a grease thickener, and optional additives. The polyamide grease thickener can range from about 1 wt% to about 50 wt% of the grease composition, and can be in the range of about 5 wt% to about 20 wt% of the grease composition. The base oil can include vegetable oils, mineral oils, synthetic oils, or any other fluid that provides lubricating properties. As an example, the grease can be silicone grease. Silicone grease can include a polydimethylsiloxane base oil. Other greases can be fluoroether-based greases that include a fluoroether base oil.

[0052] The grease thickeners present can self-assemble into a network to provide a grease having a structure suitable for functioning. As described above, the grease thickener has a weight average molecular weight in the range of about 450 g / mol to about 10,000 g / mol. It is possible for all grease thickener molecules to have the same molecular weight, but a molecular weight distribution of the grease thickener can also exist.

[0053] According to various examples, the grease thickener is a first grease thickener, and the grease composition further includes a second grease thickener having a chemical structure different from that of the first grease thickener. For example, the molecular weight of the first grease thickener can be different from the molecular weight of the second grease thickener, or the first grease thickener and the second grease thickener can have different chemical compositions, or the first grease thickener and the second grease thickener are isomers of each other.

[0054] The advantage of the grease composition is that it can provide sufficient thickening to the grease composition without substantially containing lithium, polyurea, or a mixture thereof. For example, the grease composition can contain less than 1 wt% lithium or 0 wt% lithium and / or less than 1 wt% polyurea or 0 wt% polyurea. Advantageously, this can result in a potentially more environmentally friendly grease composition. Additionally, especially with respect to substantially no lithium, the resulting grease composition can be manufactured at a lower cost compared to a corresponding grease composition using a thickener containing lithium as opposed to the claimed grease thickener.

[0055] In some embodiments, it is possible for the grease composition to include the disclosed grease thickening composition and a grease thickening composition containing lithium, polyurea, or both. However, the amount of the grease thickening composition containing the required lithium, polyurea, or both can be reduced by including the disclosed grease thickening composition compared to a grease composition not including the disclosed grease thickening composition.

[0056] In addition to the lubricant and the grease thickener, the grease composition can include additional components such as an anhydrous calcium complex, an aluminum complex, a calcium sulfonate complex, a calcium complex, a barium complex, a sodium complex, or a mixture thereof. The combined total weight % of these components (alone or in combination) can be less than 35 wt%, less than 30 wt%, less than 25 wt%, less than 20 wt%, less than 15 wt%, less than 10 wt%, less than 5 wt%, or 0 wt%.

[0057] The grease composition containing the disclosed thickener can have several beneficial properties. For example, the dropping point of the grease composition can be in the range of about 200 °C to about 280 °C, about 250 °C to about 265 °C, about 200 °C, 201, 202, 203, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 216, 217, 218, 219, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 230, 231, 232, 233, 234, 235, 236, 237, 238, 239, 240, 241, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 253, 254, 255, 256, 257, 258, 259, 260, 261, 262, 263, 264, 265, 266, 267, 268, 269, 270, 271, 272, 273, 274, 275, 276, 277, 278, 279, or less than, equal to, or greater than about 280 °C. The dropping point of the grease composition can be substantially the same as the dropping point of a comparative grease composition that differs only in that the grease thickening component is a lithium-based grease thickening component. As is generally understood, the dropping point of a grease is the temperature at which the grease transitions from a semi-solid state to a liquid state. The dropping point test determines the cohesiveness of the oil and thickener of the grease. The test for determining the dropping point is ASTM D-2265.

[0058] The grease composition also exhibits acceptable mechanical strength. For example, the NLGI consistency number of the unprocessed composition of the grease composition (a sample that has received only minimal perturbation) can be in the range of 3 to 4. The NLGI consistency number of the processed grease composition (as a sample that has been subjected to 60 double strokes by a standard grease operator) can be in the range of 1 to 2. The NLGI consistency number can be measured in accordance with ASTM D-217 entitled "Cone Penetration of Lubricating Grease". This involves two test apparatuses. The first apparatus consists of a sealed container and a piston-like plunger. The surface of the plunger is perforated so that grease can flow from one side of the plunger to the other when the plunger is operated up and down. The test grease is inserted into the container, and the plunger is stroked 60 times while maintaining the test apparatus and the grease at a temperature of 25°C. After processing, the grease is placed in a penetration test apparatus. This apparatus includes a container, a specially configured cone, and a dial indicator. The container is filled with grease and the upper surface of the grease is smoothed. The cone is positioned such that its tip just touches the grease surface, and the dial indicator is set to zero at this position. When the test is started, the cone penetrates into the grease due to its weight. After a specific time interval, the depth of penetration is measured.

[0059] As used herein, values such as P0, P 60 , and P 10000 are included to indicate the degree to which the grease composition is processed. For example, an unprocessed grease composition has a P0 value. A grease composition that is inserted into a container and has 60 plunger strokes while the test apparatus and the grease composition are maintained at a temperature of 25°C has a P 60 value. A grease composition that is inserted into a container and has 10,000 plunger strokes while the test apparatus and the grease composition are maintained at a temperature of 25°C has a P 10000 value.

[0060] The unprocessed grease composition can have a penetration value in the range of about 215 / 10 millimeters to about 255 / 10 millimeters, about 225 / 10 millimeters to about 235 / 10 millimeters, about 215 / 10 millimeters, 216, 217, 218, 219, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 230, 231, 232, 233, 234, or less than, equal to, or greater than 235 / 10 millimeters. The processed grease composition can have a penetration value in the range of about 280 / 10 millimeters to about 310 / 10 millimeters, about 290 / 10 millimeters to about 400 / 10 millimeters, about 280 / 10 millimeters, 281, 282, 283, 284, 285, 286, 287, 288, 289, 290, 291, 292, 293, 294, 295, 296, 297, 298, 299, 300, 301, 302, 303, 304, 305, 306, 307, 308, 309, 310, 311, 312, 313, 314, 315, 316, 317, 318, 319, 320, 321, 322, 323, 324, 325, 326, 327, 328, 329, 330, 331, 332, 333, 334, 335, 336, 337, 338, 339, 340, 341, 342, 343, 344, 345, 346, 347, 348, 349, 350, 351, 352, 353, 354, 355, 356, 357, 358, 359, 360, 361, 362, 363, 364, 365, 366, 367, 368, 369, 370, 371, 372, 373, 374, 375, 376, 377, 378, 379, 380, 381, 382, 383, 384, 385, 386, 387, 388, 389, 390, 391, 392, 393, 394, 395, 396, 397, 398, 399, or less than, equal to, or greater than 400 / 10 millimeters. The NLGI consistency number of the grease composition can be substantially the same as the NLGI consistency number of a comparative grease composition that differs only in that the grease thickening component is a lithium-based grease thickening component.

[0061] The grease composition can be brought into contact with any number of articles that require lubrication. For example, the grease composition can be applied to bearings, crankshafts, joints, hinges, and the like.

[0062] The grease thickener can generally be readily prepared by reacting any polycarboxylate mentioned herein with any diamine to form a first product. The first product is then reacted with any monocarboxylate described herein to form the grease thickener.

Examples

[0063] The various aspects of the present invention can be better understood with reference to the following examples provided by way of illustration. The present invention is not limited to the examples described herein.

[0064] As shown below, various grease thickeners were developed and tested for their properties. Example 1:

Chemical formula

[0065] The grease thickener of formula XV was prepared in a three-necked round bottom equipped with a nitrogen inlet and a distillation apparatus. 18.1 g (0.05 mol) of 6T6 was mixed with 28.4 g (0.1 mol) of stearic acid in 327 g of alkylated naphthalene base oil. The reaction mixture was slowly heated to 180 °C and reacted for 2 hours. During the reaction, the mixture began to thicken with the formation of water, which was removed by distillation. The temperature of the reaction mixture was raised to 220 °C over 2 hours while maintaining stirring, and the reaction was continued until the formation of water stopped. The material was cooled to 150 °C and homogenized. The grease thickener was incorporated into the grease composition at 12 wt%. The dropping point of the grease composition was 175 °C. Example 2

Chemical formula

[0066] The thickener of Formula XII was prepared in a three-necked round bottom equipped with a nitrogen inlet and a distillation apparatus. 18.1 g (0.05 mol) of 6T6 was mixed with 14.2 g (0.05 mol) of stearic acid and 6.4 g (0.05 mol) of benzoic acid in 117.5 g of ester base oil. The reaction mixture was slowly heated to 180 °C and reacted for 2 hours. During the reaction, the mixture began to thicken with the formation of water, and the water was removed by distillation. The temperature of the reaction mixture was raised to 220 °C over 2 hours, stirring was maintained, and the reaction was continued until the formation of water stopped. The material was cooled to 150 °C and homogenized. The thickener was incorporated into the grease composition at 12 wt%. The dropping point of the grease composition was 225 °C. Example 3

Chemical formula

[0067] The thickener of Formula XXXII was prepared in a three-necked round bottom equipped with a nitrogen inlet and a distillation apparatus. 25.00 g (0.0411 mol) of 6T6T6 was mixed with 23.38 g (0.0822 mol) of stearic acid and 344 g of alkylated naphthalene base oil. The reaction mixture was slowly heated to 180 °C and reacted for 2 hours. During the reaction, the mixture began to thicken with the formation of water, and the water was removed by distillation. The temperature of the reaction mixture was raised to 240 °C over 2 hours, stirring was maintained, and the reaction was continued until the formation of water stopped. The material was cooled to 150 °C and homogenized. The thickener was incorporated into the grease composition at 12 wt%. The dropping point of the grease composition was 300 °C. Example 4

Chemical formula

[0068] The thickener of Formula XI was prepared in a three-necked round bottom equipped with a nitrogen inlet and a distillation apparatus. 46.6 g (0.1285 mol) of 6T6 was mixed with 12.5 g (0.0644 mol) of dimethyl terephthalate and 4.46 g (5 wt%) of phenol in 655 g of alkylated naphthalene base oil. The mixture was heated at 100 °C for 30 minutes. 36.6 g (0.129 mol) of stearic acid was added to the reaction mixture, and the temperature was slowly raised to 180 °C and reacted for 2 hours. During the reaction, the mixture began to thicken with the formation of water, and the water was removed by distillation. The temperature of the reaction mixture was raised to 220 °C over 2 hours, stirring was maintained, and the reaction was carried out until distillation was complete. The material was cooled to 150 °C and homogenized. The thickener was incorporated into the grease composition at 12 wt%. The dropping point of the grease composition was 240 °C. Example 5 [Chemical formula]

[0069] The thickener of Formula XIII was prepared in a three-necked round bottom equipped with a nitrogen inlet and a distillation apparatus. 63.0 g (0.1738 mol) of 6T6 was mixed with 17.00 g (0.00.1159 mol) of dimethyl terephthalate and 5.58 g (5 wt%) of phenol in 818 g of alkylated naphthalene base oil. The mixture was heated at 100 °C for 30 minutes. 32.96 g (0.1159 mol) of stearic acid and 7.43 g (0.058 mol) of cyclohexanecarboxylic acid were added to the reaction mixture, and the temperature was slowly raised to 180 °C and reacted for 2 hours. The temperature of the reaction mixture was raised to 220 °C over 2 hours, stirring was maintained, and the reaction was carried out until distillation was complete. The material was cooled to 150 °C and homogenized. The thickener was incorporated into the grease composition at 12 wt%. The dropping point of the grease composition was 262 °C. Example 6

[0070] The grease thickener of formula XXXII had an amine group functionalized with stearic acid therein. As shown in Table 2 and Figure 1, the grease thickener was studied and its performance (penetration value) when present at 10 wt% and 15 wt% in the grease composition was determined. Additionally, for the thickener, 65 wt% or 95 wt% of the amine groups in the grease thickener were functionalized with stearic acid.

[0071] The data indicate that the functionalization (or incomplete functionalization) of the amine with stearic acid is an independent variable that affects the consistency of the polyamide thickened grease composition. It is observed that increasing the amount of stearic acid end-capping increases the compatibility of the thickener with the base oil system of the grease composition. At the same time, increasing the amount of stearic acid end-capping decreases the consistency of the grease composition, resulting in a softer grease. In these systems, the grease requires a higher loading of the polyamide thickener with a higher stearic acid functionality to achieve similar mechanical properties as those with a lower stearic acid functionality. For example, a thickener having 95% of its amine functionalized with stearic acid has a higher P0 / P 60 / P 10000 measurement when compared to a grease thickener of similar chain length with 65% amine functionalization at the same grease thickener loading.

Table 2

[0072] The terms and expressions that have been used are not limiting but are used as terms of explanation, and in the use of such terms and expressions, there is no intention to exclude any equivalents of the illustrated and described features or parts thereof, but it is recognized that various modifications are possible within the scope of the embodiments of the present invention. Therefore, although the present invention is specifically disclosed by specific embodiments and optional features, modifications and variations of the concepts disclosed herein may be reclassified by those skilled in the art, and it should be understood that such modifications and variations are considered to be within the scope of the embodiments of the present invention. Exemplary aspects.

[0073] The following exemplary aspects are provided, but the numerals should not be construed as specifying importance.

[0074] Aspect 1 is a polyamide grease thickener having a structure according to Formula I: (MCA-DA-)(PCA-DA) y -PCA-(DA-PCA) y (-DA-MCA)(I) wherein: In each occurrence, PCA is independently a reacted polycarboxylate, In each occurrence, MCA is independently a reacted monocarboxylate, In each occurrence, DA is independently a reacted diamine, y is 0 or an integer other than zero, the weight average molecular weight of the polyamide grease thickener is in the range of about 450 g / mol to about 3500 g / mol, the structure according to Formula I contains at least 4 amide bonds, and has at least one alicyclic moiety or aromatic moiety, providing a polyamide grease thickener.

[0075] Aspect 2 provides the polyamide grease thickener according to Aspect 1, wherein the weight average molecular weight of the polyamide grease thickener is in the range of about 500 g / mol to about 2500 g / mol.​

[0076] Aspect 3 provides a polyamide grease thickener according to any one of Aspects 1 or 2, wherein the agent has a structure according to Formula II: ((MCA-DA-)(PCA-DA) y -) n PCA(II) wherein n is 2 and y ranges from 2 to 4.

[0077] Aspect 4 provides a polyamide grease thickener according to any one of Aspects 1 to 3, wherein the agent has a structure according to Formula III: (MCA-DA)-PCA-(DA-MCA)(III)

[0078]

[0079] Aspect 5 provides a polyamide grease thickener according to any one of Aspects 1 to 4, wherein in each occurrence, PCA independently contains 6 to 50 carbon atoms.

[0080]

[0081] Aspect 6 provides a polyamide grease thickener according to any one of Aspects 1 to 5, wherein in each occurrence, PCA independently contains 6, 8, or 9 carbon atoms.

[0082] Aspect 7 provides a polyamide grease thickener according to any one of Aspects 1 to 6, wherein in each occurrence, PCA has the same chemical structure.

[0081] Aspect 8 provides a polyamide grease thickener according to any one of Aspects 1 to 7, wherein at least two occurrences of PCA have different chemical structures.

[0082] Aspect 9 provides the polyamide grease thickener according to any one of Aspects 1 to 8, wherein in each occurrence, PCA independently contains reacted adipic acid, reacted purified terephthalic acid, reacted isophthalic acid, reacted phthalic anhydride, reacted naphthenic acid, reacted mellitic acid, reacted mellitic anhydride, reacted naphthalenetetracarboxylic dianhydride, reacted citric acid, reacted ester, reacted acid chloride, reacted dianhydride, or reacted ethylenediaminetetraacetic acid.

[0083] Aspect 10 provides the polyamide grease thickener according to any one of Aspects 1 to 9, wherein in each occurrence, MCA independently contains reacted aliphatic monocarboxylate, reacted alicyclic monocarboxylate, or reacted aromatic monocarboxylate.

[0084] Aspect 11 provides the polyamide grease thickener according to any one of Aspects 1 to 10, wherein in each occurrence, MCA has the same chemical structure.

[0085] Aspect 12 provides the polyamide grease thickener according to any one of Aspects 1 to 11, wherein at least two occurrences of MCA have different chemical structures.

[0086] Aspect 13 provides the polyamide grease thickener according to any one of Aspects 1 to 12, wherein in each occurrence, MCA contains reacted monocarboxylate, and the monocarboxylate has the structure according to Formula (IV):

Chemical formula

[0087] Aspect 14 is a substituted or unsubstituted (C1-C 20 ) hydrocarbyl is independently substituted or unsubstituted (C1-C 20 ) Alkyl, substituted or unsubstituted (C3-C 20 ) Cycloalkyl, substituted or unsubstituted (C2-C 20 ) Alkenyl, substituted or unsubstituted (C2-C 20 ) alkynyl, substituted or unsubstituted (C1-C 20 ) Acyl, substituted or unsubstituted (C4-C 20 ) aryl, and substituted or unsubstituted (C2-C 20 14. The polyamide grease thickener according to claim 13, wherein the polyamide grease thickener is selected from:

[0088] Embodiment 15 is an embodiment of a compound according to the invention, wherein, at each occurrence, the MCA comprises a reacted monocarboxylate, the monocarboxylate being Formula (V): [ka] Formula (VI): [ka] The structure is In the formula, R 4 is a bond and a substituted or unsubstituted (C1-C 20 15. The polyamide grease thickener according to claim 13 or 14, wherein the polyamide grease thickener is selected from the group consisting of aryl, aryloxy ...

[0089] Aspect 16 includes, at each occurrence, substituted or unsubstituted (C1-C 20 ) hydrocarbylene is independently substituted or unsubstituted (C1-C 20 ) alkylene, substituted or unsubstituted (C3-C 20 ) Cycloalkylene, substituted or unsubstituted (C2-C 20 ) Alkenylene, substituted or unsubstituted (C2-C 20 ) Alkynylene, substituted or unsubstituted (C1-C 20 ) Acylene, substituted or unsubstituted (C4-C 20) Provide the polyamide grease thickener according to embodiment 15, which is selected from arylene and substituted or unsubstituted -O-(CH2)n- (n = 2 to 20).

[0090] Embodiment 17 provides the polyamide grease thickener according to any one of embodiments 1 to 16, wherein in each occurrence, MCA is independently selected from the reacted ester, reacted acid chloride, reacted anhydride, reacted benzoic acid, reacted cyclohexanecarboxylic acid, and reacted stearic acid.

[0091] Embodiment 18 provides the polyamide grease thickener according to any one of embodiments 1 to 17, wherein in each occurrence, DA has the same chemical structure.

[0092] Embodiment 19 provides the polyamide grease thickener according to any one of embodiments 1 to 18, wherein at least two occurrences of DA have different chemical structures.

[0093] Embodiment 20 provides the polyamide grease thickener according to any one of embodiments 1 to 19, wherein in each occurrence, DA is the reacted diamine, and the diamine independently has the structure according to formula (VII): [Chemical formula] wherein in the formula, R 5 is substituted or unsubstituted (C1 - C 20 ) alkylene, substituted or unsubstituted (C5 - C 20 ) cycloalkylene, or substituted or unsubstituted (C4 - C 20 ) aryl.

[0094] Embodiment 21 provides the polyamide grease thickener according to embodiment 20, wherein in each occurrence, DA is the reacted diamine independently selected from the reacted hexamethylenediamine, reacted propanediamine, reacted butanediamine, reacted pentanediamine, reacted phenylenediamine, reacted cyclohexanediamine, or reacted nonanediamine.

[0095] Aspect 22 provides a polyamide grease thickener according to any one of Aspects 1 to 21, wherein in each occurrence, DA is a reacted diamine independently selected from reacted hexamethylenediamine, reacted propanediamine, reacted butanediamine, or reacted pentanediamine.

[0096] Aspect 23 provides a polyamide grease thickener according to any one of Aspects 1 to 22, wherein in each occurrence, DA is reacted hexamethylenediamine.

[0097] Aspect 24 provides a polyamide grease thickener according to any one of Aspects 1 to 23, wherein the dropping point of the grease composition containing the polyamide grease thickener is above about 200 °C.

[0098] Aspect 25 provides a polyamide grease thickener according to any one of Aspects 2 to 24, wherein the dropping point of the grease composition containing the polyamide grease thickener is above about 250 °C.

[0099] Aspect 26 provides a polyamide grease thickener according to any one of Aspects 1 to 25, wherein when at least one aromatic moiety is disposed internally, at least one aromatic moiety is disubstituted in the para position, and when at least one alicyclic moiety is disposed internally, at least one alicyclic moiety is disubstituted and is symmetric with respect to the axis passing through both substituents.

[0100] Aspect 27 provides a polyamide grease thickener according to any one of Aspects 1 to 26, wherein the structure according to Formula I contains at least two aromatic moieties, and at least one aromatic moiety is a monosubstituted terminal group of Formula I.

[0101] Aspect 28 is a polyamide grease thickener having a structure according to Formula IX:

Chemical formula

[0102] Aspect 29 provides the polyamide grease thickener according to Aspect 28, in which the weight average molecular weight of the polyamide grease thickener is in the range of about 500 g / mol to about 2500 g / mol.

[0103] Aspect 30 provides the polyamide grease thickener according to any one of Aspects 28 or 29, in which in each occurrence, the MCA independently includes a reacted aliphatic monocarboxylate, a reacted alicyclic monocarboxylate, or a reacted aromatic monocarboxylate.

[0104] Aspect 31 provides the polyamide grease thickener according to any one of Aspects 28 to 30, in which in each occurrence, the MCA has the same chemical structure.

[0105] Aspect 32 provides the polyamide grease thickener according to any one of Aspects 28 to 31, in which at least two occurrences of the MCA have different chemical structures.

[0106] Aspect 33 is that in each occurrence, the MCA includes a reacted monocarboxylate, and the monocarboxylate has the formula (IV):

Chemical formula

[0107] Aspect 34 is a substituted or unsubstituted (C1-C 20 ) hydrocarbyl is independently substituted or unsubstituted (C1-C 20 ) Alkyl, substituted or unsubstituted (C3-C 20 ) Cycloalkyl, substituted or unsubstituted (C2-C 20 ) Alkenyl, substituted or unsubstituted (C2-C 20 ) alkynyl, substituted or unsubstituted (C1-C 20 ) Acyl, substituted or unsubstituted (C4-C 20 ) aryl, and substituted or unsubstituted (C2-C 20 34. The polyamide grease thickener according to claim 33, wherein the polyamide grease thickener is selected from:

[0108] Embodiment 35 is an embodiment of a compound according to the invention, wherein, at each occurrence, the MCA comprises a reacted monocarboxylate, the monocarboxylate being Formula (V): [ka] Formula (VI): [ka] The structure is In the formula, R 4 is a bond and a substituted or unsubstituted (C1-C 20 35. The polyamide grease thickener according to claim 33 or 34, wherein the polyamide grease thickener is selected from the group consisting of aryl, aryloxy ...

[0109] Aspect 36 is a substituted or unsubstituted (C1-C 20 ) hydrocarbylene is independently substituted or unsubstituted (C1-C 20 ) alkylene, substituted or unsubstituted (C3-C 20)Cycloalkylene, substituted or unsubstituted (C2 - C 20 )Alkenylene, substituted or unsubstituted (C2 - C 20 )Alkynylene, substituted or unsubstituted (C1 - C 20 )Acylen, substituted or unsubstituted (C4 - C 20 )Arylene, and the polyamide grease thickener according to embodiment 35, which is selected from substituted or unsubstituted -O-(CH2)n- (n = 2 - 20).

[0110] Embodiment 37 provides the polyamide grease thickener according to any one of embodiments 28 - 36, wherein in each occurrence, MCA is independently selected from the reacted ester, reacted acid chloride, reacted anhydride, reacted benzoic acid, reacted cyclohexanecarboxylic acid, and reacted stearic acid.

[0111] Embodiment 38 provides the polyamide grease thickener according to any one of embodiments 28 - 37, wherein in each occurrence, DA has the same chemical structure.

[0112] Embodiment 39 provides the polyamide grease thickener according to any one of embodiments 28 - 38, wherein at least two occurrences of DA have different chemical structures.

[0113] Embodiment 40 provides the polyamide grease thickener according to any one of embodiments 28 - 39, wherein in each occurrence, DA is a reacted diamine independently selected from the reacted hexamethylenediamine, reacted propanediamine, reacted butanediamine, reacted pentanediamine, reacted phenylenediamine, reacted cyclohexanediamine, or reacted nonanediamine.

[0114] Embodiment 41 provides the polyamide grease thickener according to any one of embodiments 28 - 40, wherein in each occurrence, DA is the reacted hexamethylenediamine.

[0115] Aspect 42 provides a polyamide grease thickener according to any one of Aspects 28 to 41, wherein the dropping point of the polyamide grease thickener is above about 200 °C.

[0116] Aspect 43 provides a polyamide grease thickener according to any one of Aspects 28 to 42, wherein the dropping point of the polyamide grease thickener is above about 250 °C.

[0117] Aspect 44 provides a polyamide grease thickener having a structure according to any one of Formula X, XI, XII, or XIII:

Chemical formula

[0118] Aspect 46 provides a method for using a polyamide grease thickener according to any one of Aspects 1 to 45, the method comprising contacting the polyamide grease thickener with a grease to form a grease composition. reacting a polycarboxylate with a diamine to form a first product; reacting the first product with a monocarboxylate to form a grease thickener.

[0119] Aspect 47 provides a method for using the grease composition according to Aspect 46, the method comprising contacting the grease composition with an article to be lubricated.

[0120] Aspect 48 provides a grease composition comprising a grease thickener according to any one of Aspects 1 to 47.

[0121] Aspect 49 provides a grease composition according to Aspect 48, wherein the grease thickener is in the range of about 1 wt% to about 50 wt% of the grease composition.

[0122] Aspect 49 provides a grease composition according to Aspect 48, wherein the grease thickener ranges from about 1 wt% to about 50 wt% of the grease composition.

[0123] Aspect 50 provides a grease composition according to Aspect 48 or 49, wherein the grease thickener is in the range of about 5 wt% to about 20 wt% of the grease composition.

[0124] Aspect 51 provides a grease composition according to any one of Aspects 48 to 51, wherein the grease thickener is a first grease thickener, the grease composition further comprises a second grease thickener having a chemical structure different from that of the first grease thickener, and the second grease thickener has a structure according to Formula I.

[0125] Aspect 52 provides a grease composition according to Aspect 51, wherein the molecular weight of the first grease thickener is different from the molecular weight of the second grease thickener.

[0126] Aspect 53 provides a grease composition according to Aspect 51 or 52, wherein the first grease thickener and the second grease thickener have different chemical compositions.

[0127] Aspect 54 provides a grease composition according to any one of Aspects 48 to 53, which contains less than 1 wt% of lithium.

[0128] Aspect 55 provides a grease composition according to any one of Aspects 48 to 54, which contains less than 1 wt% of polyurea.

[0129] Aspect 56 is a homogeneous grease composition, Formula I: (MCA-DA-)(PCA-DA) y -PCA-(DA-PCA) y (-DA-MCA)(I) which is a polyamide grease thickener having a structure according to, wherein, in each occurrence, PCA is independently a reacted polycarboxylate, in each occurrence, MCA is independently a reacted monocarboxylate, in each occurrence, DA is independently a reacted diamine, y is an integer that is 0 or non-zero, the structure according to formula I contains at least 4 amide bonds, There is provided a grease composition comprising a polyamide grease thickener having at least one alicyclic moiety or aromatic moiety.

[0130] Aspect 57 provides the homogeneous grease composition of Aspect 56, wherein when at least one aromatic moiety is disposed internally, at least one aromatic moiety is disubstituted in the para position, and when at least one alicyclic moiety is disposed internally, at least one alicyclic moiety is disubstituted and is symmetric with respect to the axis passing through both substituents.

[0131] Aspect 58 provides the homogeneous grease composition according to Aspect 56 or 57, wherein the structure according to formula I contains at least two aromatic moieties and at least one aromatic moiety is a monosubstituted terminal group of formula I.

[0132] Aspect 59 provides the homogeneous grease composition according to any one of Aspects 56 - 58, wherein the agent has a structure according to formula II: ((MCA-DA-)(PCA-DA) y -) n PCA(II) wherein n is 2 and y ranges from 2 to 4. There is provided the homogeneous grease composition according to any one of Aspects 56 - 58.

[0133] Aspect 60 provides the homogeneous grease composition according to any one of Aspects 56 - 59, wherein the agent has a structure according to formula III: (MCA-DA)-PCA-(DA-MCA)(III)

[0134] Aspect 61 provides the homogeneous grease composition according to any one of Aspects 56 - 60, wherein in each occurrence, PCA independently contains from 6 to 50 carbon atoms.

[0135] Aspect 62 provides, in each occurrence, a homogeneous grease composition according to any one of Aspects 56 to 61, in which PCA independently contains 6, 8, or 9 carbon atoms.

[0136] Aspect 63 provides, in each occurrence, a homogeneous grease composition according to any one of Aspects 56 to 62, in which PCA has the same chemical structure.

[0137] Aspect 64 provides a homogeneous grease composition according to any one of Aspects 56 to 63, in which at least two occurrences of PCA have different chemical structures.

[0138] Aspect 65 provides, in each occurrence, a homogeneous grease composition according to any one of Aspects 56 to 64, in which PCA independently contains reacted adipic acid, reacted purified terephthalic acid, reacted isophthalic acid, reacted phthalic anhydride, reacted naphthenic acid, reacted mellitic acid, reacted mellitic anhydride, reacted naphthalenetetracarboxylic dianhydride, reacted citric acid, reacted ester, reacted acid chloride, reacted dianhydride, or reacted ethylenediaminetetraacetic acid.

[0139] Aspect 66 provides, in each occurrence, a homogeneous grease composition according to any one of Aspects 56 to 65, in which MCA independently contains reacted aliphatic monocarboxylate, reacted alicyclic monocarboxylate, or reacted aromatic monocarboxylate.

[0140] Aspect 67 provides, in each occurrence, a homogeneous grease composition according to any one of Aspects 56 to 66, in which MCA has the same chemical structure.

[0141] Aspect 68 provides a homogeneous grease composition according to any one of Aspects 56 to 67, in which at least two occurrences of MCA have different chemical structures.

[0142] Aspect 69 provides, in each occurrence, a homogeneous grease composition in which MCA contains reacted monocarboxylate, and the monocarboxylate has the formula (IV): [Chemical formula] having a structure according to wherein R 3 is a substituted or unsubstituted (C1-C 20 ) hydrocarbyl, and R 7 is selected from -OH, -Cl, -O - , or a substituted or unsubstituted -O-(C1-C 20 ) hydrocarbyl, to provide a homogeneous grease composition according to any one of Aspects 56 to 68.

[0143] Aspect 70 is, in each occurrence, that the substituted or unsubstituted (C1-C 20 ) hydrocarbyl is independently a substituted or unsubstituted (C1-C 20 ) alkyl, a substituted or unsubstituted (C3-C 20 ) cycloalkyl, a substituted or unsubstituted (C2-C 20 ) alkenyl, a substituted or unsubstituted (C2-C 20 ) alkynyl, a substituted or unsubstituted (C1-C 20 ) acyl, a substituted or unsubstituted (C4-C 20 ) aryl, and a substituted or unsubstituted (C2-C 20 ) alkoxy, to provide a homogeneous grease composition according to Aspect 69.

[0144] Aspect 71 is, in each occurrence, that the MCA contains a reacted monocarboxylate, and the monocarboxylate has the formula (V): [Chemical formula] has the formula (VI): [Chemical formula] having a structure according to wherein R 4 is selected from a bond and a substituted or unsubstituted (C1-C 20 ) hydrocarbylene, to provide a homogeneous grease composition according to Aspect 69 or 70.

[0145] Aspect 72 provides, in each occurrence, a homogeneous grease composition according to Aspect 71, wherein a substituted or unsubstituted (C1-C 20 ) hydrocarbylene is independently selected from a substituted or unsubstituted (C1-C 20 ) alkylene, a substituted or unsubstituted (C3-C 20 ) cycloalkylene, a substituted or unsubstituted (C2-C 20 ) alkenylene, a substituted or unsubstituted (C2-C 20 ) alkynylene, a substituted or unsubstituted (C1-C 20 ) acylene, a substituted or unsubstituted (C4-C 20 ) arylene, and a substituted or unsubstituted -O-(CH2)n- (n = 2 - 20).

[0146] Aspect 73 provides, in each occurrence, a homogeneous grease composition according to any one of Aspects 56 - 72, wherein the MCA is independently selected from a reacted ester, a reacted acid chloride, a reacted anhydride, a reacted benzoic acid, a reacted cyclohexanecarboxylic acid, and a reacted stearic acid.

[0147] Aspect 74 provides, in each occurrence, a homogeneous grease composition according to any one of Aspects 56 - 73, wherein the DA has the same chemical structure.

[0148] Aspect 75 provides, in each occurrence, a homogeneous grease composition according to any one of Aspects 56 - 74, wherein at least two occurrences of the DA have different chemical structures.

[0149] Aspect 76 provides, in each occurrence, a homogeneous grease composition according to any one of Aspects 56 - 75, wherein the DA is a reacted diamine, and the diamine independently has a structure according to formula (VII):

Chemical formula

[0150] Aspect 77 provides the homogeneous grease composition according to Aspect 76, wherein in each occurrence, DA is a reacted diamine independently selected from the reacted hexamethylenediamine, reacted propanediamine, reacted butanediamine, reacted pentanediamine, reacted phenylenediamine, reacted cyclohexanediamine, or reacted nonanediamine.

[0151] Aspect 78 provides the homogeneous grease composition according to any one of Aspects 56 to 77, wherein in each occurrence, DA is a reacted diamine independently selected from the reacted hexamethylenediamine, reacted propanediamine, reacted butanediamine, or reacted pentanediamine.

[0152] Aspect 79 provides the homogeneous grease composition according to any one of Aspects 56 to 78, wherein in each occurrence, DA is the reacted hexamethylenediamine.

[0153] Aspect 80 provides the homogeneous grease composition according to any one of Aspects 56 to 79, wherein the dropping point of the grease composition is above about 200 °C.

[0154] Aspect 81 provides the homogeneous grease composition according to any one of Aspects 56 to 80, wherein the dropping point of the grease composition is above about 250 °C.

[0155] Aspect 82 provides the polyamide grease thickener according to any one of Aspects 1 to 43 and 45 to 81, wherein in each occurrence, MCA, PCA, and DA do not contain branched alkyl.

[0156] Aspect 83 provides a polyamide grease thickener according to any one of Aspects 1 to 43 and 45 to 82, wherein the polyamide grease thickener contains at least two alicyclic moieties, at least two aromatic moieties, or at least one alicyclic moiety and at least one aromatic moiety.

[0157] Aspect 84 provides a polyamide grease thickener according to any one of Aspects 1 to 43 and 45 to 83, wherein any disubstituted alicyclic moiety and any disubstituted aromatic moiety are symmetric with respect to an axis extending through the two substituents.

[0158] Aspect 85 provides a polyamide grease thickener according to any one of Aspects 1 to 43 and 45 to 84, wherein any disubstituted aromatic moiety is para-substituted.

[0159] Aspect 86 is a polyamide grease thickener having a structure according to Formula VIII: (MCA-DA-(ZZ) y -) x PCA(VIII) wherein, in the formula, in each occurrence, ZZ is

Chemical formula

Chemical formula

[0160] Aspect 87 provides a polyamide grease thickener according to Aspect 86, wherein the agent has a structure represented by Formula I: (MCA-DA-)(PCA-DA) y -PCA-(DA-PCA) y (-DA-MCA)(I)

[0161] Aspect 88 provides a polyamide grease thickener according to Aspect 86 or 87, wherein the agent has a structure represented by Formula II: ((MCA-DA-)(PCA-DA) y -) n PCA(II) wherein n ranges from 2 to 4.

[0162] Aspect 89 provides a polyamide grease thickener according to any one of Aspects 86 to 88, wherein the agent has a structure represented by Formula III: (MCA-DA)-PCA-(DA-MCA)(III)

[0163] Aspect 90 provides a polyamide grease thickener according to any one of Aspects 86 to 89, wherein in each occurrence, PCA independently contains 3 to 50 carbon atoms.

[0164] Aspect 91 provides a polyamide grease thickener according to any one of Aspects 86 to 90, wherein in each occurrence, PCA independently contains 6, 8, or 9 carbon atoms.

[0165] Aspect 92 provides a polyamide grease thickener according to any one of Aspects 86 to 91, wherein in each occurrence, PCA contains a reacted polycarboxylate, and the polycarboxylate has Formula (X):

Chemical formula

Chemical formula

[0166] Aspect 93 is that, in each occurrence, the substituted or unsubstituted (C1-C 20 ) hydrocarbyl is, independently, a substituted or unsubstituted (C1-C 20 ) alkyl, a substituted or unsubstituted (C3-C 20 ) cycloalkyl, a substituted or unsubstituted (C2-C 20 ) alkenyl, a substituted or unsubstituted (C2-C 20 ) alkynyl, a substituted or unsubstituted (C1-C 20 ) acyl, a substituted or unsubstituted (C4-C 20 ) aryl, and a substituted or unsubstituted (C2-C 20 ) alkoxy, providing the polyamide grease thickener according to aspect 92.

[0167] Aspect 94 is that, in each occurrence, PCA has the same chemical structure, providing the polyamide grease thickener according to any one of aspects 86 to 93.

[0168] Aspect 95 is that at least two occurrences of PCA have different chemical structures, providing the polyamide grease thickener according to any one of aspects 86 to 94.

[0169] Aspect 96 provides, in each occurrence, a polyamide grease thickener according to any one of Aspects 86 to 95, wherein the PCA independently comprises reacted adipic acid, reacted purified terephthalic acid, reacted isophthalic acid, reacted phthalic anhydride, reacted naphthoic acid, reacted mellitic acid, reacted mellitic anhydride, reacted naphthalenetetracarboxylic dianhydride, reacted citric acid, reacted ester, reacted acid chloride, reacted dianhydride, or reacted ethylenediaminetetraacetic acid.

[0170] Aspect 97 provides, in each occurrence, a polyamide grease thickener according to any one of Aspects 86 to 96, wherein the MCA independently comprises reacted aliphatic monocarboxylate, reacted alicyclic monocarboxylate, or reacted aromatic monocarboxylate.

[0171] Aspect 98 provides, in each occurrence, a polyamide grease thickener according to any one of Aspects 86 to 97, wherein the MCA has the same chemical structure.

[0172] Aspect 99 provides a polyamide grease thickener according to any one of Aspects 86 to 98, wherein at least two occurrences of the MCA have different chemical structures.

[0173] Aspect 100 provides, in each occurrence, a polyamide grease thickener according to any one of Aspects 86 to 99, wherein the MCA comprises reacted monocarboxylate, and the monocarboxylate has the structure according to Formula (IV):

Chemical formula

[0174] Aspect 101, at each occurrence, is substituted or unsubstituted (C1-C 20 ) hydrocarbyl is independently substituted or unsubstituted (C1-C 20 ) Alkyl, substituted or unsubstituted (C3-C 20 ) Cycloalkyl, substituted or unsubstituted (C2-C 20 ) Alkenyl, substituted or unsubstituted (C2-C 20 ) alkynyl, substituted or unsubstituted (C1-C 20 ) Acyl, substituted or unsubstituted (C4-C 20 ) aryl, and substituted or unsubstituted (C2-C 20 101. The polyamide grease thickener according to claim 100, wherein the polyamide grease thickener is selected from:

[0175] Embodiment 102 is an embodiment of the present invention, wherein, at each occurrence, the MCA comprises a reacted monocarboxylate, the monocarboxylate being Formula (V): [ka] Formula (VI): [ka] The structure is In the formula, R 4 is a bond and a substituted or unsubstituted (C1-C 20 102. The polyamide grease thickener according to any one of claims 100 to 101, wherein the polyamide grease thickener is selected from the group consisting of aryl, aryloxy ...

[0176] Aspect 103, at each occurrence, is substituted or unsubstituted (C1-C 20 ) hydrocarbylene is independently substituted or unsubstituted (C1-C 20 ) alkylene, substituted or unsubstituted (C3-C 20 ) Cycloalkylene, substituted or unsubstituted (C2-C 20 ) Alkenylene, substituted or unsubstituted (C2-C 20 ) Alkynylene, substituted or unsubstituted (C1-C 20 ) Acylene, substituted or unsubstituted (C4-C 20)Provide the polyamide grease thickener according to embodiment 102, which is selected from arylene and substituted or unsubstituted -O-(CH2)n- (n = 2 to 20).

[0177] In embodiment 104, each occurrence, MCA is independently selected from the reacted ester, reacted acid chloride, reacted anhydride, reacted benzoic acid, reacted cyclohexanecarboxylic acid, and reacted stearic acid, and provides the polyamide grease thickener according to any one of embodiments 86 to 103.

[0178] In embodiment 105, each occurrence, DA has the same chemical structure, and provides the polyamide grease thickener according to any one of embodiments 86 to 104.

[0179] In embodiment 106, at least two occurrences of DA have different chemical structures, and provides the polyamide grease thickener according to any one of embodiments 86 to 105.

[0180] In embodiment 107, each occurrence, DA is the reacted diamine, and the diamine is independently of the formula (VII):

Chemical formula

[0181] In embodiment 108, each occurrence, the substituted or unsubstituted (C1~C 20 ) hydrocarbylene is independently substituted or unsubstituted (C1~C 20 ) alkylene, substituted or unsubstituted (C3~C 20 ) cycloalkylene, substituted or unsubstituted (C2~C 20 ) alkenylene, substituted or unsubstituted (C2~C 20 ) alkynylene, substituted or unsubstituted (C1~C 20 ) acylen, substituted or unsubstituted (C4~C20 ) arylene, and substituted or unsubstituted (C2-C 20 ) provides the polyamide grease thickener according to aspect 107, selected from alkoxylene.

[0182] Aspect 109 provides, in each occurrence, the polyamide grease thickener according to any one of aspects 86 to 108, wherein DA is a reacted diamine independently selected from reacted hexamethylenediamine, reacted propanediamine, reacted butanediamine, reacted pentanediamine, reacted nonanediamine, reacted isononanediamine, reacted 2-methylpentamethylenediamine, reacted ethylenediamine, reacted isophoronediamine, reacted m-xylylenediamine, and reacted m-phenylenediamine.

[0183] Aspect 110 provides, in each occurrence, the polyamide grease thickener according to any one of aspects 86 to 109, wherein DA is reacted hexamethylenediamine.

[0184] Aspect 111 provides the polyamide grease thickener according to any one of aspects 86 to 110, wherein x, y, and z are independently in the range of 1 to 10.

[0185] Aspect 112 provides the polyamide grease thickener according to any one of aspects 86 to 111, wherein x, y, and z are independently in the range of 1 to 3.

[0186] Aspect 113 provides the polyamide grease thickener according to any one of aspects 86 to 112, wherein the molecular weight of the grease thickener is at least 1000 g / mol.

[0187] Aspect 114 provides the polyamide grease thickener according to any one of aspects 86 to 113, wherein the molecular weight of the grease thickener is at least 1500 g / mol.

[0188] Aspect 115 provides a polyamide grease thickener according to any one of Aspects 86 to 114, wherein the weight average molecular weight of the grease thickener ranges from about 1000 g / mol to about 10,000 g / mol.

[0189] Aspect 116 provides a polyamide grease thickener according to any one of Aspects 86 to 115, wherein the weight average molecular weight of the grease thickener ranges from about 1200 g / mol to about 4000 g / mol.

[0190] Aspect 117 provides a grease composition comprising a grease thickener according to any one of Aspects 86 to 116.

[0191] Aspect 118 provides a grease composition according to Aspect 117, wherein the grease thickener ranges from about 1 wt% to about 50 wt% of the grease composition.

[0192] Aspect 119 provides a grease composition according to Aspect 117 or 118, wherein the grease thickener ranges from about 5 wt% to about 20 wt% of the grease composition.

[0193] Aspect 120 provides a grease composition according to any one of Aspects 117 to 119, wherein the grease thickener is a first grease thickener, and the grease composition further comprises a second grease thickener having a chemical structure different from that of the first grease thickener, and the second grease thickener has a structure according to Formula VIII.

[0194] Aspect 121 provides a grease composition according to Aspect 120, wherein the molecular weight of the first grease thickener is different from that of the second grease thickener.

[0195] Aspect 122 provides a grease composition according to Aspect 120 or 121, wherein the first grease thickener and the second grease thickener have different chemical compositions.

[0196] Aspect 123 provides a grease composition according to any one of Aspects 117 to 122, comprising less than 1 wt% lithium.

[0197] Aspect 124 provides a grease composition according to any one of Aspects 117 to 123, which contains less than 1% by weight of polyurea.

[0198] Aspect 125 provides a grease composition containing a reaction product of a polycarboxylate, a diamine, and a monocarboxylate according to any one of Aspects 92 to 124.

[0199] Aspect 126 provides a grease composition containing a reaction product of a polycarboxylate, a diamine, and a monocarboxylate according to any one of Aspects 92 to 125.

[0200] Aspect 127 provides a grease composition according to any one of Aspects 117 to 126, in which the total weight percentage of components selected from calcium anhydride, aluminum complex, calcium sulfonate complex, calcium complex, barium complex, sodium complex, and polyurea is less than 35% by weight.

[0201] Aspect 128 provides a method of using a polyamide grease thickener according to any one of Aspects 86 to 127, which includes bringing the polyamide grease thickener into contact with grease.

[0202] Aspect 129 provides a method of using a grease composition according to any one of Aspects 117 to 128, which includes bringing the grease composition into contact with an article to be lubricated.

[0203] Aspect 130 provides a method of producing a grease thickener according to any one of Aspects 86 to 129, reacting a polycarboxylate with a diamine to form a first product, reacting the first product with a monocarboxylate to form a grease thickener.

Claims

1. Formula I: (MCA-DA-)(PCA-DA) ｙ -PCA-(DA-PCA) ｙ (-DA-MCA)(I) A polyamide grease thickener having a structure according to, wherein, In each occurrence, PCA is independently a reacted polycarboxylate, In each occurrence, MCA is independently a reacted monocarboxylate In each occurrence, DA is independently a reacted diamine, y is an integer other than 0 or zero, The weight average molecular weight of the polyamide grease thickener is in the range of about 450 g / mol to about 3500 g / mol, A polyamide grease thickener having at least one alicyclic moiety or aromatic moiety.

2. The polyamide grease thickener according to claim 1, wherein the weight average molecular weight of the polyamide grease thickener is in the range of about 500 g / mol to about 2500 g / mol.

3. The agent has a structure according to Formula II: ((MCA-DA-)(PCA-DA) ｙ -) ｎ PCA(II) having a structure according to, wherein n is 2 and y is in the range of 2 to 4, the polyamide grease thickener according to claim 1 or 2.

4. The agent has a structure according to Formula III: (MCA-DA)-PCA-(DA-MCA)(III) The polyamide grease thickener according to any one of claims 1 to 3, having a structure according to.

5. In each occurrence, PCA is independently a polycarboxylate containing 6 to 50 carbon atoms, the polyamide grease thickener according to any one of claims 1 to 4.

6. In each occurrence, the PCA independently contains 6, 8, or 9 carbon atoms, and the polyamide grease thickener according to any one of claims 1 to 5.

7. In each occurrence, the PCA independently contains reacted adipic acid, reacted purified terephthalic acid, reacted isophthalic acid, reacted phthalic anhydride, reacted naphthoic acid, reacted mellitic acid, reacted mellitic anhydride, reacted naphthalenetetracarboxylic dianhydride, reacted citric acid, reacted ester, reacted acid chloride, reacted dianhydride, or reacted ethylenediaminetetraacetic acid, and the polyamide grease thickener according to any one of claims 1 to 6.

8. In each occurrence, the MCA independently contains reacted aliphatic monocarboxylate, reacted alicyclic monocarboxylate, or reacted aromatic monocarboxylate, and the polyamide grease thickener according to any one of claims 1 to 7.

9. In each occurrence, the DA is a reacted diamine, and the diamine independently has a structure according to formula (VII): 【Chemical Formula 1】 and wherein R ５ is substituted or unsubstituted (C １ - C ２０ ) alkylene, substituted or unsubstituted (C ５ - C ２０ ) cycloalkylene, or substituted or unsubstituted (C ４ - C ２０ ) aryl, and the polyamide grease thickener according to any one of claims 1 to 8.

10. In each occurrence, the DA is a reacted diamine independently selected from reacted hexamethylenediamine, reacted propanediamine, reacted butanediamine, reacted pentanediamine, reacted phenylenediamine, reacted cyclohexanediamine, or reacted nonanediamine, the polyamide grease thickener according to claim 9.

11. In each occurrence, the DA is reacted hexamethylenediamine, the polyamide grease thickener according to any one of claims 1 to 10.

12. The dropping point of the grease composition containing the polyamide grease thickener is more than about 200 ° C, the polyamide grease thickener according to any one of claims 1 to 11.

13. The dropping point of the grease composition containing the polyamide grease thickener is more than about 250 ° C, the polyamide grease thickener according to any one of claims 2 to 12.

14. When the at least one aromatic moiety is disposed internally, the at least one aromatic moiety is disubstituted at the para position, and when the at least one alicyclic moiety is disposed internally, the at least one alicyclic moiety is disubstituted and is symmetric with respect to the axis passing through both substituents, the polyamide grease thickener according to any one of claims 1 to 13.

15. Formula IX: 【Chemical Formula 2】 A polyamide grease thickener having a structure according to Wherein In each occurrence, the PCA is independently a para-substituted reacted polycarboxylate, In each occurrence, the MCA is independently a reacted monocarboxylate, In each occurrence, the DA is independently a reacted diamine, y is 0 or an integer other than zero, A polyamide grease thickener in which the weight average molecular weight of the polyamide grease thickener is in the range of about 450 g / mol to about 3500 g / mol.

16. The polyamide grease thickener according to claim 15, wherein the weight average molecular weight of the polyamide grease thickener is in the range of about 500 g / mol to about 2500 g / mol.

17. In each occurrence, MCA contains a reacted monocarboxylate, and the monocarboxylate has the formula (IV): 【Chemical formula 3】 having the structure according to wherein R ３ is a substituted or unsubstituted (C １ - C ２０ ) hydrocarbyl, and R ７ is -OH, -Cl, -O － or a substituted or unsubstituted -O-(C １ - C ２０ ) hydrocarbyl selected from the group consisting of: the polyamide grease thickener according to claim 15 or 16.

18. In each occurrence, the substituted or unsubstituted (C １ - C ２０ ) hydrocarbyl is independently a substituted or unsubstituted (C １ - C ２０ ) alkyl, a substituted or unsubstituted (C ３ - C ２０ ) cycloalkyl, a substituted or unsubstituted (C ２ - C ２０ ) alkenyl, a substituted or unsubstituted (C ２ - C ２０ ) alkynyl, a substituted or unsubstituted (C １ - C ２０ ) acyl, a substituted or unsubstituted (C ４ - C ２０ ) aryl, and a substituted or unsubstituted (C ２ - C ２０ ) alkoxy selected from the group consisting of: the polyamide grease thickener according to claim 17.

19. In each occurrence, the MCA contains the reacted monocarboxylate, and the monocarboxylate has Formula (V): 【Chemical Formula 4】 Formula (VI): 【Chemical Formula 5】 a structure according to wherein R ４ is selected from a bond and a substituted or unsubstituted (C １ ~C ２０ ) hydrocarbylene, the polyamide grease thickener according to claim 17 or 18.

20. In each occurrence, the substituted or unsubstituted (C １ ~C ２０ ) hydrocarbylene is independently a substituted or unsubstituted (C １ ~C ２０ ) alkylene, a substituted or unsubstituted (C ３ ~C ２０ ) cycloalkylene, a substituted or unsubstituted (C ２ ~C ２０ ) alkenylene, a substituted or unsubstituted (C ２ ~C ２０ ) alkynylene, a substituted or unsubstituted (C １ ~C ２０ ) acylen, a substituted or unsubstituted (C ４ ~C ２０ ) arylene, and a substituted or unsubstituted -O-(CH ２ )n-(n = 2 to 20) selected from, the polyamide grease thickener according to claim 19.

21. In each occurrence, the MCA is independently selected from the reacted ester, the reacted acid chloride, the reacted anhydride, the reacted benzoic acid, the reacted cyclohexanecarboxylic acid, and the reacted stearic acid, the polyamide grease thickener according to any one of claims 15 to 20.

22. In each occurrence, the DA has the same chemical structure, the polyamide grease thickener according to any one of claims 15 to 21.

23. The polyamide grease thickener according to any one of claims 15 to 22, wherein at least two occurrences of DA have different chemical structures.

24. The polyamide grease thickener according to any one of claims 15 to 23, wherein in each occurrence, DA is a reacted diamine independently selected from reacted hexamethylenediamine, reacted propanediamine, reacted butanediamine, reacted pentanediamine, reacted phenylenediamine, reacted cyclohexanediamine, or reacted nonanediamine.

25. The polyamide grease thickener according to any one of claims 15 to 24, wherein in each occurrence, DA is reacted hexamethylenediamine.

26. The polyamide grease thickener according to any one of claims 15 to 25, wherein the dropping point of the polyamide grease thickener is above about 200 °C.

27. The polyamide grease thickener according to any one of claims 15 to 26, wherein the dropping point of the polyamide grease thickener is above about 250 °C.

28. A polyamide grease thickener having a structure according to any one of formulae X, XI, XII, or XIII: 【Chemical Formula 6】

29. A polyamide grease thickener having a structure according to formula VIII: (MCA-DA-(ZZ) ｙ -) ｘ PCA(VIII), wherein in each occurrence, ZZ is 【Chemical Formula 7】 and X is 【Chemical Formula 8】 and In each occurrence, the PCA is, independently, a reacted polycarboxylate, In each occurrence, the MCA is, independently, a reacted monocarboxylate, In each occurrence, the DA is, independently, a reacted diamine, x is an integer other than zero, y is 0 or an integer other than zero, z is 0 or an integer other than zero, a polyamide grease thickener.

30. In each occurrence, the PCA includes a reacted polycarboxylate, and the polycarboxylate is Formula (X): [Chemical Formula 9] Formula (XVII): [Chemical Formula 10] Formula (XVIII): [Chemical Formula 11] has a structure according to In the formula, in each occurrence, R １ and R ２ are, independently, a bond or a substituted or unsubstituted (C １ - C ２０ ) hydrocarbyl, and in each occurrence, R ６ is -OH, -Cl, -O － , or a substituted or unsubstituted -O-(C １ - C ２０ ) hydrocarbyl selected from, the polyamide grease thickener according to claim 29.

31. In each occurrence, the substituted or unsubstituted (C １ - C ２０ ) hydrocarbyl is, independently, a substituted or unsubstituted (C １ - C ２０ ) alkyl, a substituted or unsubstituted (C ３ - C ２０ ) cycloalkyl, a substituted or unsubstituted (C ２ - C ２０ ) alkenyl, a substituted or unsubstituted (C ２ - C ２０ ), alkynyl, substituted or unsubstituted (C １ ~C ２０ ), acyl, substituted or unsubstituted (C ４ ~C ２０ aryl, and substituted or unsubstituted (C ２ ~C ２０ ) alkoxy selected from, the polyamide grease thickener according to claim 30.

32. In each occurrence, MCA contains the reacted monocarboxylate, and the monocarboxylate has the formula (IV): 【Chemical Formula 12】 has the structure according to, In the formula, R ３ is substituted or unsubstituted (C １ ~C ２０ ) hydrocarbyl, R ７ is -OH, -Cl, -O － , or substituted or unsubstituted -O-(C １ ~C ２０ ) hydrocarbyl selected from, the polyamide grease thickener according to claim 30 or 31.

33. In each occurrence, the substituted or unsubstituted (C １ ~C ２０ ) hydrocarbyl is independently substituted or unsubstituted (C １ ~C ２０ ) alkyl, substituted or unsubstituted (C ３ ~C ２０ ) cycloalkyl, substituted or unsubstituted (C ２ ~C ２０ ) alkenyl, substituted or unsubstituted (C ２ ~C ２０ ) alkynyl, substituted or unsubstituted (C １ ~C ２０ ) acyl, substituted or unsubstituted (C ４ ~C ２０ aryl, and substituted or unsubstituted (C ２ ~C ２０ ) alkoxy selected from, the polyamide grease thickener according to claim 32.

34. In each occurrence, the MCA contains the reacted monocarboxylate, and the monocarboxylate has the structure according to Formula (V): 【Chemical Formula 13】 Formula (VI): 【Chemical Formula 14】 and in the formula, R is selected from bonding and substituted or unsubstituted (C ４ ~C １ ~C ２０ ) hydrocarbylene. The polyamide grease thickener according to claim 32 or 33.

35. In each occurrence, the substituted or unsubstituted (C １ ~C ２０ ) hydrocarbylene is independently selected from substituted or unsubstituted (C １ ~C ２０ ) alkylene, substituted or unsubstituted (C ３ ~C ２０ ) cycloalkylene, substituted or unsubstituted (C ２ ~C ２０ ) alkenylene, substituted or unsubstituted (C ２ ~C ２０ ) alkynylene, substituted or unsubstituted (C １ ~C ２０ ) acylen, substituted or unsubstituted (C ４ ~C ２０ ) arylene, and substituted or unsubstituted -O-(CH ２ )n-(n = 2 to 20). The grease thickener according to claim 34.

36. In each occurrence, the DA is the reacted diamine, and the diamine independently has the structure according to Formula (VII): 【Chemical Formula 15】 and in the formula, R is substituted or unsubstituted (C ５ ~C １ ~C ２０ ) hydrocarbylene. The polyamide grease thickener according to any one of claims 29 to 35.

37. In each occurrence, the substituted or unsubstituted (C １ ~C ２０ ) hydrocarbylene is independently a substituted or unsubstituted (C １ ~C ２０ ) alkylene, a substituted or unsubstituted (C ３ ~C ２０ ) cycloalkylene, a substituted or unsubstituted (C ２ ~C ２０ ) alkenylene, a substituted or unsubstituted (C ２ ~C ２０ ) alkynylene, a substituted or unsubstituted (C １ ~C ２０ ) acylen, a substituted or unsubstituted (C ４ ~C ２０ ) arylene, and a substituted or unsubstituted (C ２ ~C ２０ ) alkoxylene, the polyamide grease thickener according to claim 36.

38. In each occurrence, DA is a reacted diamine independently selected from reacted hexamethylenediamine, reacted propanediamine, reacted butanediamine, reacted pentanediamine, reacted nonanediamine, reacted isononanediamine, reacted 2-methylpentamethylenediamine, reacted ethylenediamine, reacted isophoronediamine, reacted m-xylylenediamine, and reacted m-phenylenediamine, the polyamide grease thickener according to any one of claims 29 to 37.

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