N-alkylated antidegradants

Abstract

The present disclosure provides compounds represented by Formula (I): (I), or salts or solvates thereof, wherein R1, R1a, R2a, R2b, R2c, R2d, R3, and R3a are as defined in the specification. The present disclosure also provides compositions, vulcanized elastomeric articles, lubricant compositions, combustible fuel compositions, and fuel additive compositions comprising a compound disclosed herein. The present disclosure also provides processes for preparing the compositions and vulcanized elastomeric articles described herein. The present disclosure also provides a process for retreading tires using a composition described herein. The present disclosure also provides kits comprising a composition described herein.

Description

N-ALKYLATED ANTIDEGRADANTSSTATEMENT OF GOVERNMENTAL INTEREST

[0001] This invention was made with government support under ED25HDQ0G0013 awarded by the Department of Commerce Economic Development Administration. The government has certain rights in the invention.BACKGROUNDField

[0002] The present disclosure provides compounds with anti degradant, e.g., antiozonant, antioxidant and / or antifatigue, properties that are useful additives for vulcanized rubber articles, compositions comprising elastomers, lubricants, fuels, and other compositions which require such properties or in compositions which are themselves useful as compositions to impart such properties.Background

[0003] Many materials such as plastics, elastomers, elastomeric products (tires, belts, hoses, bushings, mounts, vibration isolators, etc.), lubricants and petroleum products (such as hydraulic fluids, oils, fuels and oil / fuel additives for automotive and aviation applications) are prone to degradation upon prolonged exposure to light, heat, oxygen, ozone, repetitive mechanical actions and the like. Accordingly, compounds and compositions demonstrating antidegradant efficacy are well known in the art. For example, U.S Patent No. 8,987,515 discloses an aromatic polyamine useful in inhibiting oxidative degradation particularly in lubricant compositions. U.S. Patent Application Publication No.2014 / 0316163 discloses antioxidant macromolecules with purported improved solubility in many commercially available oils and lubricants.

[0004] Anti degradants useful in the manufacture of articles formed from elastomers, plastics and the like require a very specific combination of qualities that can be difficult to achieve. While the anti degradants must obviously have commercially acceptable efficacy, they must also exhibit that efficacy over prolonged periods of time associated with use of the article, particularly at exposed surfaces of the article where degradation fromenvironmental factors such as light, oxygen and ozone primarily occurs. Just as important to the protection of surface exposed components, efficacy in protecting imbedded components of composite materials from the effects of oxidative aging and repetitive mechanical action are critically important. The anti degradants must achieve these results while not negatively impacting other additives' efficacy or desirable characteristics in the final article. Further, anti degradants which provide or improve the mechanical fatigue life after an article has been in service, aged oxidatively or by exposure to ozone are highly valued since these will inherently improve the useful mechanical service life of article. Consequently, elastomeric articles which undergo repeated mechanical flexure, extension, or compression during service would greatly benefit from such a discovery.

[0005] Articles formed from general purpose elastomers such as natural rubber, in particular tires, are especially prone to degradation from both oxygen and ozone. As discussed in U.S. Patent No. 2,905,654, the effect on rubber from degradation by oxygen is different from the effect from degradation from ozone; however, both effects can be detrimental to tire performance, appearance and life expectancy. Fatigue and crack propagation are also issues of specific concern, in particular for steel belt edge areas and tire sidewalls which are subject to significant stresses and stretching forces while flexed whether inflated, partially inflated, uninflated and throughout the service life of the tire. U.S. Patent No. 8,833,417 describes an antioxidant system that purportedly increases longterm resistance to fatigue and crack propagation over the known antioxidants discussed immediately below.

[0006] Materials with antidegradant efficacy are well known in the art for use in tire applications and are commercially available. For example, A,A-disubstituted- paraphenylenediamines such as those sold under the trademark Santoflex® are generally favored by many tire manufacturers for this purpose. EP 3147321 Al discloses rubber compositions, tires, amine compounds, and anti-aging agents, and in particular, a rubber composition that is said to be suitable for use in tread rubber or sidewall rubber of a tire.BRIEF SUMMARY

[0007] The present disclosure provides compounds that are useful as anti degradants, e.g., antiozonants, and / or antioxidants, and / or as additives in lubricants or combustible fuels, represented by Formulae (I) or (II) below and / or disclosed in Tables 1-3 below, collectivelyreferred to herein as "Compounds of the Disclosure" or individually as a "Compound of the Disclosure."

[0008] The present disclosure also provides compositions comprising:(i) a Compound of the Disclosure; and(ii) one or more elastomers; or(iii) one or more fillers; or(iv) one or more rubber chemicals; or(v) one or more plasticizers; or(vi) one or more additional anti degradants; or(vii) a combination of one or more elastomers, one or more fillers, one or more rubber chemicals, one or more plasticizers, and / or one or more additional antidegradants, collectively referred to herein as "Compositions of the Disclosure" or individually as a "Composition of the Disclosure."

[0009] The present disclosure also provides Compositions of the Disclosure comprising a Compound of the Disclosure and one or more elastomers.

[0010] The present disclosure also provides Compositions of the Disclosure comprising a Compound of the Disclosure and one or more fillers.

[0011] The present disclosure also provides Compositions of the Disclosure comprising a Compound of the Disclosure and one or more rubber chemicals.

[0012] The present disclosure also provides Compositions of the Disclosure comprising a Compound of the Disclosure and one or more plasticizers.

[0013] The present disclosure also provides Compositions of the Disclosure comprising a Compound of the Disclosure and one or more additional anti degradants.

[0014] The present disclosure also provides Compositions of the Disclosure comprising a Compound of the Disclosure and one or more carriers.

[0015] The present disclosure also provides processes for preparing a composition comprising a Compound of the Disclosure and one or more carriers, the process comprising admixing the compound and the one or more carriers.

[0016] The present disclosure also provides vulcanized elastomeric articles comprising a Compound of the Disclosure.

[0017] The present disclosure also provides vulcanized elastomeric articles prepared using a composition described herein, e.g., Compositions of the Disclosure or compositions comprising a Compound of the Disclosure and one or more carriers.

[0018] The present disclosure also provides a process for preparing the vulcanized elastomeric articles described herein, the process comprising:(a) forming a composition described herein into a formed shape; and(b) vulcanizing the formed shapeto provide a vulcanized elastomeric article.

[0019] The present disclosure also provides lubricant compositions comprising a lubricant and a Compound of the Disclosure.

[0020] The present disclosure also provides combustible fuel compositions comprising a combustible fuel and a Compound of the Disclosure.

[0021] The present disclosure also provides fuel additive compositions comprising a fuel additive and a Compound of the Disclosure.

[0022] The present disclosure also provides a process for retreading tires, the process comprising:(a) applying a composition described herein to a tire;(b) disposing a pre-vulcanized tread around the tire;(c) disposing a curing envelope around the tire; and(d) vulcanizing the tire.

[0023] The present disclosure also provides kits comprising a composition described herein and instructions for using the composition in a vulcanizable elastomeric composition.

[0024] The present disclosure also provides kits comprising a composition described herein and instructions for using the composition to prepare a vulcanized elastomeric article.

[0025] Additional embodiments and advantages of the disclosure will be set forth, in part, in the description that follows, and will flow from the description, or can be learned by practice of the disclosure. The embodiments and advantages of the disclosure will be realized and attained by means of the elements and combinations particularly pointed out in the appended claims.

[0026] It is to be understood that both the foregoing summary and the following detailed description are exemplary and explanatory only, and are not restrictive of the invention as claimed.DETAILED DESCRIPTION

[0027] In one embodiment, Compounds of the Disclosure are compounds having Formula (I):or a salt, solvate, or stereoisomer thereof, wherein:R1is selected from the group consisting of C1-C12 alkyl, C3-Cs cycloalkyl, and optionally substituted phenyl;Rlais selected from the group consisting of hydrogen, C1-C4 alkyl, and -C(=O)CH3;R2a, R2b, R2C, and R2dare each independently selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-Cs cycloalkyl, Ci-Cs alkoxy, and Ci-Cs alkylthio;R3is selected from the group consisting of C1-C12 alkyl, C3-Cs cycloalkyl, and optionally substituted phenyl; andR3ais selected from the group consisting of hydrogen and C1-C4 alkyl.

[0028] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein Rlais selected from the group consisting of hydrogen and C1-C4 alkyl.

[0029] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), with the proviso that at least one of Rlaand R3ais C1-C4 alkyl.

[0030] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein Rlais C1-C4 alkyl.

[0031] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein R3ais C1-C4 alkyl.

[0032] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein Rlais C1-C4 alkyl and R3ais C1-C4 alkyl.

[0033] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein R1is substituted phenyl.

[0034] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein R1is 2-methylphenyl.

[0035] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein R3is substituted phenyl

[0036] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein R3is 2-methylphenyl.

[0037] In some embodiments, Compounds of the Disclosure are compounds having Formula (II):(II),or a salt, solvate, or stereoisomer thereof, wherein:R1, Rla, R2a, R2b, R2C, R2d, and R3are defined in connection with Formula (I).

[0038] In some embodiments, Compounds of the Disclosure are compounds having Formula (I) or (II), wherein R1is selected from the group consisting of C1-C12 alkyl and C3-C8 cycloalkyl.

[0039] In some embodiments, Compounds of the Disclosure are compounds having Formula (I) or (II), wherein when Rlais methyl, R2a, R2b, R2c, and R2dare hydrogen, and R3is phenyl, then R1is C4-C12 alkyl or Cs-Cs cycloalkyl.

[0040] In some embodiments, Compounds of the Disclosure are compounds having Formula (I) or (II), wherein R2a, R2b, R2c, and R2dare each hydrogen or C1-C9 alkyl.

[0041] In some embodiments, Compounds of the Disclosure are compounds having Formula (I) or (II), wherein R2a, R2b, R2c, and R2dare each hydrogen.

[0042] In some embodiments, Compounds of the Disclosure are compounds having Formula (I) or (II), wherein R1is C1-C12 alkyl.

[0043] In some embodiments, Compounds of the Disclosure are compounds having Formula (I) or (II), wherein R1is branched C3-C12 alkyl.

[0044] In some embodiments, Compounds of the Disclosure are compounds having Formula (I) or (II), wherein R1is selected from the group consisting of:

[0045] In some embodiments, Compounds of the Disclosure are compounds having Formula (I) or (II), wherein R1is Cs-Cs cycloalkyl.

[0046] In some embodiments, Compounds of the Disclosure are compounds having Formula (I) or (II), wherein R1is selected from the group consisting of:

[0047] In some embodiments, Compounds of the Disclosure are compounds having Formula (I) or (II), wherein R1is:

[0048] In some embodiments, Compounds of the Disclosure are compounds having Formula (I) or (II), wherein Rlais methyl or ethyl.

[0049] In some embodiments, Compounds of the Disclosure are compounds having Formula (I) or (II), wherein Rlais ethyl.

[0050] In some embodiments, Compounds of the Disclosure are compounds having Formula (I) or (II), wherein Rlais methyl.

[0051] In some embodiments, Compounds of the Disclosure are compounds having Formula (I) or (II), wherein R3is optionally substituted phenyl.

[0052] In some embodiments, Compounds of the Disclosure are compounds having Formula (I) or (II), wherein R3is phenyl.

[0053] In some embodiments, Compounds of the Disclosure are compounds having Formula (I) or (II), wherein R3is C1-C12 alkyl.

[0054] In some embodiments, Compounds of the Disclosure are compounds having Formula (I) or (II), wherein R3is branched C1-C12 alkyl.

[0055] In some embodiments, Compounds of the Disclosure are compounds having Formula (I) or (II), wherein R3is selected from the group consisting of:

[0056] In some embodiments, Compounds of the Disclosure are compounds having Formula (I) or (II), wherein R3is Cs-Cs cycloalkyl.

[0057] In some embodiments, Compounds of the Disclosure are compounds having Formula (I) or (II), wherein R3is selected from the group consisting of:

[0058] In some embodiments, Compounds of the Disclosure are compounds having Formula (I) or (II), wherein R3is:

[0059] In some embodiments, Compounds of the Disclosure are compounds having Formula (I) or (II), wherein:R1is selected from the group consisting of:Rlais methyl or ethyl;R2a, R2b, R2C, and R2dare each hydrogen; andR3is selected from the group consisting of:

[0060] having Formula (I) or (II), wherein:R1is selected from the group consisting of:Rlais methyl or ethyl;R2a, R2b, R2c, and R2dare each hydrogen; andR3is optionally substituted phenyl.

[0061] In some embodiments, Compounds of the Disclosure are compounds having Formula (I) or (II), wherein:R1is Cs-Cs cycloalkyl;Rlais methyl or ethyl;R2a, R2b, R2C, and R2dare each hydrogen; andR3is optionally substituted phenyl.

[0062] In some embodiments, Compounds of the Disclosure are compounds having Formula (I) or (II), wherein:R1is C3-C8 cycloalkyl;Rlais methyl or ethyl;R2a, R2b, R2C, and R2dare each hydrogen; andR3is C3-C8 cycloalkyl.

[0063] In some embodiments, Compounds of the Disclosure are compounds having Formula (I) or (II), wherein:R1is:Rlais methyl or ethyl;R2a, R2b, R2c, and R2dare each hydrogen; andR3is:

[0064] In some embodiments, Compounds of the Disclosure are any one or more of the compounds of Table 1, or a salt or solvate thereof.Table 1"

[0065] In some embodiments, Compounds of the Disclosure are any one or more of the compounds of Table 2, or a salt or solvate thereof.Table 2"

[0066] In some embodiments, Compounds of the Disclosure are any one or more of the compounds of Table 3, or a salt or solvate thereof.Table 3

[0067] In some embodiments, Compounds of the Disclosure are any one or more of the compounds of Table 1, Table 2, and / or Table 3, or a salt or solvate thereof.

[0068] Compounds of the Disclosure can be useful as antidegradants, e.g., antiozonants and / or antioxidants, as additives in lubricants, and as additives in combustible fuels.

[0069] Compounds of the Disclosure can be prepared by reacting an amine-containing compound, e.g, a phenylenediamine, with an alkylating agent, e.g., methyl iodide, in the presence of a base, e.g., K2CO3, in a solvent, e.g., DMF, as shown in Scheme 1.Scheme 1X = leaving group, e.g., Cl, OTf, Br, I

[0070] Compounds of the Disclosure can also be prepared by (1) reacting an alkylamine- containing compound, e.g, methylaminobenzene, with a halogenated or tosylated nitrobenzene, e.g., 4-chloronitrobenzene, in the presence of a catalyst, e.g., Pd2(dba)3, a ligand, e.g., XPhos, and a base, e.g., sodium tert-butoxide, in a solvent, e.g., toluene, and (2) reacting the product of step (1) with hydrogen at high pressure, e.g., 650 psi, in the presence of a catalyst, e.g., platinum, a ketone, e.g., methyl isobutyl ketone, an acid, e.g., H3PO4, and a solvent, e.g., isopropanol, as shown in Scheme 2.Scheme 2cat.ligand2) acid R = CpCn alkyl; andX = Cl, OTf, Br, I solvent R1d= H or alkyl, wherein the total number of heat carbon atoms in R1c+ R1d= 1-11; orR1cand R1dtogether with the atom to which they are attached form a C3-C8cycloalkylDefinitions

[0071] The term "alkyl" as used herein by itself or as part of another group refers to a straight- or branched-chain aliphatic hydrocarbon containing one to twelve carbon atoms, i.e., a C1-C12 alkyl, or the number of carbon atoms designated, e.g., C1-C3 alkyl such as methyl, ethyl, propyl, or isopropyl; a C1-C4 alkyl such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or t-butyl; and so on. In one embodiment the alkyl is a straightchain alkyl. In another embodiment, the alkyl is a branched-chain alkyl. In one embodiment, the alkyl is a Ci-Cs alkyl. In another embodiment, the alkyl is a Ci-Ce alkyl. In another embodiment, the alkyl is a C1-C4 alkyl. In another embodiment, the alkyl is a C1-C3 alkyl. Non-limiting exemplary C1-C12 alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, ec-butyl, tert-butyl, iso-butyl, 3-pentyl, hexyl, heptyl, octyl, nonyl, and decyl.

[0072] The term "optionally substituted alkyl" as used herein by itself or as part of another group refers to an alkyl that is either unsubstituted or substituted with one to three substituents, wherein the substituents are each independently nitro, cyano, hydroxyl, amino, (e.g., -NH2, alkylamino, or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, cycloalkyl, or -C(=O)ORlh, wherein Rlhis Ci-C6alkyl.

[0073] The term "halo" or "halogen" as used herein by itself or as part of another group refers to -Cl, -F, -Br, or -I.

[0074] The term "nitro" as used herein by itself or as part of another group refers to -NO2.

[0075] The term "cyano" as used herein by itself or as part of another group refers to -CN.

[0076] The term "hydroxy" as herein used by itself or as part of another group refers to -OH.

[0077] The term "amino" as used by itself or as part of another group refers to a radical of the formula -NRlfRlg, wherein Rlfand Rlgare independently hydrogen or alkyl.

[0078] In one embodiment, the amino is -NH2.

[0079] In another embodiment, the amino is an "alkylamino," i.e., an amino group wherein Rlfis C1-6 alkyl and Rlgis hydrogen. In one embodiment, Rlfis C1-C4 alkyl. Non-limiting exemplary alkylamino groups include -N(H)CH3 and -N(H)CH2CH3.

[0080] In another embodiment, the amino is a "dialkylamino," i.e., an amino group wherein Rlfand Rlgare each independently C1-6 alkyl. In one embodiment, Rlfand Rlgare each independently C1-C4 alkyl. Non-limiting exemplary dialkylamino groups include -N(CH3)2 and -N(CH3)CH2CH(CH3)2.

[0081] The term "alkylcarbonyl" as used herein by itself or as part of another group refers to a carbonyl group, i.e., -C(=O)-, substituted by an alkyl group. In one embodiment, the alkyl is a C1-C4 alkyl. A non-limiting exemplary alkylcarbonyl group is -COCH3.

[0082] The term "haloalkyl" as used herein by itself or as part of another group refers to an alkyl substituted by one or more fluorine, chlorine, bromine, and / or iodine atoms. In one embodiment, the alkyl is substituted by one, two, or three fluorine and / or chlorine atoms. In another embodiment, the alkyl is substituted by one, two, or three fluorine atoms. In another embodiment, the alkyl is a Ci-Ce alkyl and the resulting haloalkyl is referred to as a "Ci-Ce haloalkyl." In another embodiment, the alkyl is a C1-C4 alkyl and the resulting haloalkyl is referred to as a "C1-C4 haloalkyl." In another embodiment, the alkyl group is a Ci or C2 alkyl. Non-limiting exemplary haloalkyl groups include fluoromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, 1,1 -difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3, 3, 3 -trifluoropropyl, 4,4,4-trifluorobutyl, and trichloromethyl groups.

[0083] The term "alkoxy" as used herein by itself or as part of another group refers to an alkyl attached to a terminal oxygen atom. In one embodiment, the alkyl is a Ci-Ce alkyl, and the resulting alkoxy is referred to as a "Ci-Ce alkoxy." In another embodiment, the alkyl is a C1-C4 alkyl group and thus the resulting alkoxy is referred to as a "C1-C4 alkoxy." Non-limiting exemplary alkoxy groups include methoxy, ethoxy, and / c / V-butoxy.

[0084] The term "alkylthio" as used herein by itself or as part of another group refers to an alkyl group attached to a terminal sulfur atom. In one embodiment, the alkyl is a Ci-Ce alkyl, and the resulting alkylthio is referred to as a "Ci-Ce alkylthio." In one embodiment, the alkyl group is a C1-C4 alkyl group and the resulting alkylthio is referred to as a "C1-C4 alkylthio." Non-limiting exemplary alkylthio groups include -SCH3, and -SCH2CH3.

[0085] The term "cycloalkyl" as used herein by itself or as part of another group refers to saturated and partially unsaturated, e.g., containing one or two double bonds, monocyclic, bicyclic, or tricyclic aliphatic hydrocarbons containing three to twelve carbon atoms, i.e., a C3-C12 cycloalkyl, or the number of carbons designated, e.g., a C3-C6 cycloalkyl such a cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. In one embodiment, the cycloalkyl is bicyclic, i.e., it has two rings. In another embodiment, the cycloalkyl is monocyclic, i.e., it has one ring. In another embodiment, the cycloalkyl is a C3-C8 cycloalkyl. In another embodiment, the cycloalkyl is a C3-C6 cycloalkyl. In another embodiment, the cycloalkyl is a Cs cycloalkyl, i.e., cyclopentyl. In another embodiment, the cycloalkyl is a Ce cycloalkyl, i.e., cyclohexyl. Non-limiting exemplary C3-C12 cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, norbornyl, decalin, adamantyl, cyclohexenyl, and spiro[3.3]heptane.

[0086] The term "optionally substituted phenyl" as used herein by itself or as part of another group refers to phenyl that is either unsubstituted or substituted with one to five substitutents, wherein the substituents are each independently halo, nitro, cyano, hydroxyl, amino, (e.g., -NH2, alkylamino, or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl, or cycloalkyl.

[0087] The term "heterocyclo" or "heterocyclyl" as used herein by itself or as part of another group refers to saturated and partially unsaturated, e.g., containing one or two double bonds, monocyclic, bicyclic, or tricyclic groups containing three to eighteen ring members, i.e., a 3- to 18-membered heterocyclo, comprising one, two, three, or four heteroatoms. Each heteroatom is independently oxygen, sulfur, or nitrogen. Each sulfur atom may be independently oxidized to give a sulfoxide, i.e., S(=O), or sulfone, i.e., S(=O)2. The term heterocyclo includes groups wherein one or more -CH2- groups is replaced with one or more -C(=O)- groups, including cyclic ureido groups such as imidazolidinyl-2-one, cyclic amide groups such as pyrrolidin-2-one or piperidin-2-one, and cyclic carbamate groups such as oxazolidinyl-2-one. The term heterocyclo also includes groups having fused optionally substituted aryl or optionally substituted heteroaryl groups such as indoline, indolin-2-one, 2,3-dihydro-lH-pyrrolo[2,3-c]pyridine, 2, 3,4,5- tetrahydro-lH-benzo[d]azepine, or l,3,4,5-tetrahydro-2H-benzo[d]azepin-2-one. In some embodiments, heterocyclo is a 6-membered ring comprising one nitrogen atom. The heterocyclo may be fused to the rest of the molecule to form a bicyclic group, e.g., 1,2- dihydroquinoline or 1,2,3,4-tetrahydroquinoline.

[0088] The term "optionally substituted heterocyclo" or "optionally substituted heterocyclyl" as used herein by itself or part of another group refers to a heterocyclo group that is either unsubstituted or substituted with one to four substituents, wherein the substituents are each independently halo, nitro, cyano, hydroxyl, amino, (e.g., -NH2, alkylamino, or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl, or cycloalkyl.

[0089] The term "heteroaryl" as used herein by itself or as part of another group refers to monocyclic aromatic ring systems having five to six ring members, i.e., a 5- to 6-membered heteroaryl, comprising one, two, three, four, or five heteroatoms. Each heteroatom is independently oxygen, sulfur, or nitrogen. In one embodiment, the heteroaryl has three heteroatoms. In another embodiment, the heteroaryl has two heteroatoms. In another embodiment, the heteroaryl has one heteroatom. In another embodiment, the heteroaryl has 5 ring atoms, e.g., furyl, a 5-membered heteroaryl having four carbon atoms and one oxygen atom. In another embodiment, the heteroaryl has 6 ring atoms, e.g., pyridyl, a 6-membered heteroaryl having five carbon atoms and one nitrogen atom. Non-limiting exemplary heteroaryl groups include thienyl, furyl, pyranyl, 2 / 7-pyrrolyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, thiazolyl, isothiazolyl, and isoxazolyl. In one embodiment, the heteroaryl is chosen from thienyl (e.g., thien-2-yl and thien-3-yl), furyl (e.g., 2-furyl and 3-furyl), pyrrolyl (e.g., lH-pyrrol-2-yl and 1H- pyrrol-3-yl), imidazolyl (e.g., 2H-imidazol-2-yl and 2H-imidazol-4-yl), pyrazolyl (e.g., lH-pyrazol-3-yl, lH-pyrazol-4-yl, and lH-pyrazol-5-yl), pyridyl (e.g., pyridin-2-yl, pyri din-3 -yl, and pyridin-4-yl), pyrimidinyl (e.g., pyrimidin-2-yl, pyrimidin-4-yl, and pyrimidin-5-yl), thiazolyl (e.g., thiazol-2-yl, thiazol-4-yl, and thiazol-5-yl), isothiazolyl (e.g., isothiazol-3-yl, isothiazol-4-yl, and isothiazol-5-yl), oxazolyl (e.g., oxazol-2-yl, oxazol-4-yl, and oxazol-5-yl) and isoxazolyl (e.g., isoxazol-3-yl, isoxazol-4-yl, and isoxazol-5-yl). The term heteroaryl also includes N-oxides. A non-limiting exemplary N- oxide is pyridyl N-oxide.

[0090] The term "optionally substituted heteroaryl" as used herein by itself or as part of another group refers to a heteroaryl that is either unsubstituted or substituted with one to four substituents, wherein the substituents are each independently halo, nitro, cyano, hydroxyl, amino, (e.g., -NH2, alkylamino, or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl, or cycloalkyl.

[0091] As used herein, the term "stereoisomers" is a general term for all isomers of an individual molecule that differ only in the orientation of their atoms in space. It includesenantiomers and isomers of compounds with more than one chiral center that are not mirror images of one another (diastereomers).

[0092] The term "chiral center" or "asymmetric carbon atom" refers to a carbon atom to which four different groups are attached.

[0093] The terms "enantiomer" and "enantiomeric" refer to a molecule that cannot be superimposed on its mirror image and hence is optically active wherein the enantiomer rotates the plane of polarized light in one direction and its mirror image compound rotates the plane of polarized light in the opposite direction.

[0094] The term "racemic" refers to a mixture of equal parts of enantiomers and which mixture is optically inactive.

[0095] The term "absolute configuration" refers to the spatial arrangement of the atoms of a chiral molecular entity (or group) and its stereochemical description, e.g., R or S.

[0096] The stereochemical terms and conventions used in the specification are meant to be consistent with those described in Pure & AppL Chem 65:2193 (1996), unless otherwise indicated.

[0097] The term "enantiomeric excess" or "ee" refers to a measure for how much of one enantiomer is present compared to the other. For a mixture of R and S enantiomers, the percent enantiomeric excess is defined as | R - S | *100, where R and S are the respective mole or weight fractions of enantiomers in a mixture such that R + S = 1. With knowledge of the optical rotation of a chiral substance, the percent enantiomeric excess is defined as ([a]obs / [a]max)*100, where [a]obsis the optical rotation of the mixture of enantiomers and [a]max is the optical rotation of the pure enantiomer. Determination of enantiomeric excess is possible using a variety of analytical techniques, including NMR spectroscopy, chiral column chromatography, or optical polarimetry.

[0098] In thin layer chromatography (TLC), the term Rf stands for retention factor. Rf is defined as the distance travelled by an individual component divided by the total distance travelled by the eluent. Its value is always between zero and one.

[0099] Salts and solvates, e.g., hydrates, of the Compounds of the Disclosure can also be used in the methods disclosed herein.

[0100] The present disclosure encompasses the preparation and use of salts of Compounds of the Disclosure. Salts of Compounds of the Disclosure can be prepared during the final isolation and purification of the compounds or separately by reacting the compound with an acid having a suitable cation. Salts of Compounds of the Disclosure can be acid additionsalts formed with acceptable acids. Examples of acids which can be employed to form salts include inorganic acids such as nitric, boric, hydrochloric, hydrobromic, sulfuric, and phosphoric, and organic acids such as oxalic, maleic, succinic, and citric. Non-limiting examples of salts of compounds of the disclosure include, but are not limited to, the hydrochloride, hydrobromide, hydroiodide, sulfate, bisulfate, 2-hydroxyethansulfonate, phosphate, hydrogen phosphate, acetate, adipate, alginate, aspartate, benzoate, bisulfate, butyrate, camphorate, camphorsulfonate, di gluconate, glycerolphosphate, hemi sulfate, heptanoate, hexanoate, formate, succinate, fumarate, maleate, ascorbate, isethionate, salicylate, methanesulfonate, mesitylenesulfonate, naphthylenesulfonate, nicotinate, 2-naphthalenesulfonate, oxalate, pamoate, pectinate, persulfate, 3-phenylproprionate, picrate, pivalate, propionate, tri chloroacetate, trifluoroacetate, phosphate, glutamate, bicarbonate, paratoluenesulfonate, undecanoate, lactate, citrate, tartrate, gluconate, methanesulfonate, ethanedi sulfonate, benzene sulfonate, and p-toluenesulfonate salts. In addition, available amino groups present in the compounds of the disclosure can be quatemized with methyl, ethyl, propyl, and butyl chlorides, bromides, and iodides; dimethyl, diethyl, dibutyl, and diamyl sulfates; decyl, lauryl, myristyl, and steryl chlorides, bromides, and iodides; and benzyl and phenethyl bromides. In light of the foregoing, any reference to Compounds of the Disclosure appearing herein is intended to include Compounds of the Disclosure as well as salts, hydrates, or solvates thereof.

[0101] The present disclosure encompasses the preparation and use of solvates of Compounds of the Disclosure. The term "solvate" as used herein is a combination, physical association and / or solvation of a compound of the present disclosure with a solvent molecule such as, e.g., a disolvate, monosolvate or hemisolvate, where the ratio of solvent molecule to compound of the present disclosure is about 2:1, about 1:1 or about 1:2, respectively. This physical association involves varying degrees of ionic and covalent bonding, including hydrogen bonding. In certain instances, the solvate can be isolated, such as when one or more solvent molecules are incorporated into the crystal lattice of a crystalline solid. Thus, "solvate" encompasses both solution-phase and isolatable solvates. Compounds of the Disclosure can be present as solvated forms with a solvent, such as water, methanol, and ethanol, and it is intended that the disclosure includes both solvated and unsolvated forms of Compounds of the Disclosure.

[0102] One type of solvate is a hydrate. A "hydrate" relates to a particular subgroup of solvates where the solvent molecule is water. Preparation of solvates is known in the art.See, for example, M. Caira et al, J. Pharmaceut. Sci., 93(3):601-611 (2004), which describes the preparation of solvates of fluconazole with ethyl acetate and with water. Similar preparation of solvates, hemisolvates, hydrates, and the like are described by van Tonder et al., AAPS Pharm. Sci. Tech., 5(7):Article 12 (2004), and A.L. Bingham et al., Chem. Commun. 603-604 (2001). A typical, non-limiting, process of preparing a solvate would involve dissolving a Compound of the Disclosure in a desired solvent (organic, water, or a mixture thereof) at temperatures above 20°C to about 25°C, then cooling the solution at a rate sufficient to form crystals, and isolating the crystals by known methods, e.g., filtration. Analytical techniques such as infrared spectroscopy can be used to confirm the presence of the solvent in a crystal of the solvate.

[0103] The use of the terms "a", "an", "the", and similar referents in the context of describing the disclosure (especially in the context of the claims) are to be construed to cover both the singular and the plural, unless otherwise indicated. Recitation of ranges of values herein merely are intended to serve as a shorthand method of referring individually to each separate value falling within the range, unless otherwise indicated herein, and each separate value is incorporated into the specification as if it were individually recited herein. The use of any and all examples, or exemplary language (e.g., "such as") provided herein, is intended to better illustrate the disclosure and is not a limitation on the scope of the disclosure unless otherwise claimed. No language in the specification should be construed as indicating any non-claimed element as essential to the practice of the disclosure.

[0104] Furthermore, "and / or" where used herein is to be taken as specific disclosure of each of the two specified features or components with or without the other. Thus, the term "and / or" as used in a phrase such as "A and / or B" herein is intended to include "A and B," "A or B," "A" (alone), and "B" (alone). Likewise, the term "and / or" as used in a phrase such as "A, B, and / or C" is intended to encompass each of the following aspects: A, B, and C; A, B, or C; A or C; A or B; B or C; A and C; A and B; B and C; A (alone); B (alone); and C (alone).

[0105] It is understood that wherever aspects are described herein with the language "comprising," otherwise analogous aspects described in terms of "consisting of' and / or "consisting essentially of are also provided.

[0106] The term "wt / wt %" as used herein refers to the mass of one component in a composition or blend, e.g., a composition comprising a Compound of the Disclosure and one or more elastomers; or a Composition of the Disclosure and one or more fillers; or ablend comprising two or more elastomers, etc., divided by the combined mass of all components in the composition or blend, times 100. For example, the wt / wt % of a Compound of the Disclosure in a composition comprising 1 kg of the compound, 1 kg natural rubber, and 2 kg of synthetic rubber, is 25 wt / wt % (1 kg / 4 kg = 0.25 x 100 = 25 wt / wt %). The wt / wt % of a Compound of the Disclosure in a composition comprising 1 kg of the compound and 1 kg of carbon black is 50 wt / wt % (1 kg / 2 kg = 0.20 x 100 = 50 wt / wt %). The wt / wt % of a Compound of the Disclosure in a composition comprising 1 kg of the compound, 1 kg natural rubber, 2 kg of synthetic rubber, and 1 kg of carbon black is 20 wt / wt % (1 kg / 5 kg = 0.20 x 100 = 20 wt / wt %). The wt / wt % of natural rubber in a blend of one or more elastomers comprising 20 kg natural rubber and 30 kg synthetic rubber is 40 wt / wt % (20 kg / 50 kg = 0.40 x 100 = 40 wt / wt %).

[0107] As used herein, the term "masterbatch" refers to a composition comprising at least one elastomer and a Compound of the Disclosure. In some embodiments, the masterbatch comprises from about 5 wt / wt % to about 95 wt / wt % of at least one elastomer and from about 5 wt / wt % to about 95 wt / wt % of a Compound of the Disclosure. In some embodiments, the masterbatch comprises about 5 wt / wt %, about 10 wt / wt %, about 15 wt / wt %, about 20 wt / wt %, about 25 wt / wt %, about 30 wt / wt %, about 35 wt / wt %, about 40 wt / wt %, about 45 wt / wt %, about 50 wt / wt %, about 55 wt / wt %, about 60 wt / wt %, about 65 wt / wt %, about 70 wt / wt %, about 75 wt / wt %, about 80 wt / wt %, about 85 wt / wt %, about 90 wt / wt %, or about 95 wt / wt % of a Compound of the Disclosure. In some embodiments, the masterbatch comprises about 5 wt / wt %, about 10 wt / wt %, about 15 wt / wt %, about 20 wt / wt %, about 25 wt / wt %, about 30 wt / wt %, about 35 wt / wt %, about 40 wt / wt %, about 45 wt / wt %, about 50 wt / wt %, about 55 wt / wt %, about 60 wt / wt %, about 65 wt / wt %, about 70 wt / wt %, about 75 wt / wt %, about 80 wt / wt %, about 85 wt / wt %, about 90 wt / wt %, or about 95 wt / wt % of at least one elastomer.

[0108] As used herein, the term "premix" refers to a composition comprising a Compound of the Disclosure and at least one additional component, e.g., a filler, a rubber chemical, a plasticizer, an additional anti degradant, or a combination thereof. In some embodiments, the premix does not comprise an elastomer. In some embodiments, the premix comprises from about 5 wt / wt % to about 95 wt / wt % of a Compound of the Disclosure and from about 5 wt / wt % to about 95 wt / wt % of the least one additional component, e.g., a filler, a rubber chemical, a plasticizer, an additional antidegradant, or a combination thereof. In some embodiments, the premix comprises about 5 wt / wt %, about 10 wt / wt %, about 15wt / wt %, about 20 wt / wt %, about 25 wt / wt %, about 30 wt / wt %, about 35 wt / wt %, about 40 wt / wt %, about 45 wt / wt %, about 50 wt / wt %, about 55 wt / wt %, about 60 wt / wt %, about 65 wt / wt %, about 70 wt / wt %, about 75 wt / wt %, about 80 wt / wt %, about 85 wt / wt %, about 90 wt / wt %, or about 95 wt / wt % of a Compound of the Disclosure. In some embodiments, the premix comprises about 5 wt / wt %, about 10 wt / wt %, about 15 wt / wt %, about 20 wt / wt %, about 25 wt / wt %, about 30 wt / wt %, about 35 wt / wt %, about 40 wt / wt %, about 45 wt / wt %, about 50 wt / wt %, about 55 wt / wt %, about 60 wt / wt %, about 65 wt / wt %, about 70 wt / wt %, about 75 wt / wt %, about 80 wt / wt %, about 85 wt / wt %, about 90 wt / wt %, or about 95 wt / wt % of at least one additional component, e.g., a filler, a rubber chemical, a plasticizer, an additional anti degradant, or a combination thereof.

[0109] The term "one or more" as used herein is intended to mean that at least one component in a relevant category of components, e.g. one or more elastomers, or at least one component in a disclosed list, e.g., one or more fluorine, chlorine, bromine, and / or iodine atoms, is present and, in some embodiments, more than one component is present. In some embodiments, one or more means 1 to 50. In some embodiments, one or more means 1 to 40. In some embodiments, one or more means 1 to 30. In some embodiments, one or more means 1 to 20. In some embodiments, one or more means 1 to 10. In some embodiments, one or more means 1 to 5. In some embodiments, one or more means 1 to 3. In some embodiments, one or more means 1 or 2. In some embodiments, one or more means 1.Compositions and Methods of Use

[0110] In another embodiment, the disclosure provides compositions comprising:(i) a Compound of the Disclosure; and(ii) one or more elastomers; or(iii) one or more fillers; or(iv) one or more rubber chemicals; or(v) one or more plasticizers; or(vi) one or more additional anti degradants; or(vii) a combination of one or more elastomers, one or more fillers, one or more rubber chemicals, one or more plasticizers, and / or one or more additional anti degradants.[OHl] In some embodiments, a Composition of the Disclosure comprises from about 15 wt / wt % to about 85 wt / wt % of a Compound of the Disclosure. In some embodiments,the composition comprises from about 1 wt / wt % to about 5 wt / wt %, from about 1 wt / wt % to about 15 wt / wt %, from about 1 wt / wt % to about 25 wt / wt %, from about 1 wt / wt % to about 35 wt / wt %, from about 1 wt / wt % to about 45 wt / wt %, from about 1 wt / wt % to about 55 wt / wt %, from about 1 wt / wt % to about 65 wt / wt %, from about 1 wt / wt % to about 75 wt / wt %, from about 1 wt / wt % to about 85 wt / wt %, from about 1 wt / wt % to about 95 wt / wt %, from about 5 wt / wt % to about 15 wt / wt %, from about 5 wt / wt % to about 25 wt / wt %, from about 5 wt / wt % to about 35 wt / wt %, from about 5 wt / wt % to about 45 wt / wt %, from about 5 wt / wt % to about 55 wt / wt %, from about 5 wt / wt % to about 65 wt / wt %, from about 5 wt / wt % to about 75 wt / wt %, from about 5 wt / wt % to about 85 wt / wt %, from about 5 wt / wt % to about 95 wt / wt %, from about 15 wt / wt % to about 25 wt / wt %, from about 15 wt / wt % to about 35 wt / wt %, from about 15 wt / wt % to about 45 wt / wt %, from about 15 wt / wt % to about 55 wt / wt %, from about 15 wt / wt % to about 65 wt / wt %, from about 15 wt / wt % to about 75 wt / wt %, from about 15 wt / wt % to about 95 wt / wt %, from about 25 wt / wt % to about 35 wt / wt %, from about 25 wt / wt % to about 45 wt / wt %, from about 25 wt / wt % to about 55 wt / wt %, from about 25 wt / wt % to about 65 wt / wt %, from about 25 wt / wt % to about 75 wt / wt %, from about 25 wt / wt % to about 85 wt / wt %, from about 25 wt / wt % to about 95 wt / wt %, from about 35 wt / wt % to about 45 wt / wt %, from about 35 wt / wt % to about 55 wt / wt %, from about 35 wt / wt % to about 65 wt / wt %, from about 35 wt / wt % to about 75 wt / wt %, from about 35 wt / wt % to about 85 wt / wt %, from about 35 wt / wt % to about 95 wt / wt %, from about 45 wt / wt % to about 55 wt / wt %, from about 45 wt / wt % to about 65 wt / wt %, from about 45 wt / wt % to about 75 wt / wt %, from about 45 wt / wt % to about 85 wt / wt %, from about 45 wt / wt % to about 95 wt / wt %, from about 55 wt / wt % to about 65 wt / wt %, from about 55 wt / wt % to about 75 wt / wt %, from about 55 wt / wt % to about 85 wt / wt %, from about 55 wt / wt % to about 95 wt / wt %, from about 65 wt / wt % to about 75 wt / wt %, from about 65 wt / wt % to about 85 wt / wt %, from about 65 wt / wt % to about 95 wt / wt %, from about 75 wt / wt % to about 85 wt / wt %, from about 75 wt / wt % to about 95 wt / wt %, or from about 85 wt / wt % to about 95 wt / wt % of a Compound of the Disclosure. In some embodiments, the composition comprises from about 0.1 wt / wt% to about 0.5 wt / wt%, from about 0.1 wt / wt% to about 1 wt / wt%, from about 0.1 wt / wt% to about 1.5 wt / wt%, from about 0.1 wt / wt% to about 2 wt / wt%, from about 0.1 wt / wt% to about 2.5 wt / wt%, from about 0.1 wt / wt% to about 3 wt / wt%, from about 0.1 wt / wt% to about 3.5 wt / wt%, from about 0.1 wt / wt% to about 4 wt / wt%, from about 0.1 wt / wt% to about 4.5 wt / wt%, from about 0.1 wt / wt% toabout 5 wt / wt%, from about 0.1 wt / wt% to about 6 wt / wt%, from about 0.1 wt / wt% to about 7 wt / wt%, from about 0.1 wt / wt% to about 8 wt / wt%, from about 0.1 wt / wt% to about 9 wt / wt%, from about 0.1 wt / wt% to about 10 wt / wt%, from about 0.5 wt / wt% to about 1 wt / wt%, from about 0.5 wt / wt% to about 1.5 wt / wt%, from about 0.5 wt / wt% to about 2 wt / wt%, from about 0.5 wt / wt% to about 2.5 wt / wt%, from about 0.5 wt / wt% to about 3 wt / wt%, from about 0.5 wt / wt% to about 3.5 wt / wt%, from about 0.5 wt / wt% to about 4 wt / wt%, from about 0.5 wt / wt% to about 4.5 wt / wt%, from about 0.5 wt / wt% to about 5 wt / wt%, from about 0.5 wt / wt% to about 6 wt / wt%, from about 0.5 wt / wt% to about 7 wt / wt%, from about 0.5 wt / wt% to about 8 wt / wt%, from about 0.5 wt / wt% to about 9 wt / wt%, from about 0.5 wt / wt% to about 10 wt / wt%, from about 1 wt / wt% to about 2 wt / wt%, from about 1 wt / wt% to about 2.5 wt / wt%, from about 1 wt / wt% to about 3 wt / wt%, from about 1 wt / wt% to about 3.5 wt / wt%, from about 1 wt / wt% to about 4 wt / wt%, from about 1 wt / wt% to about 4.5 wt / wt%, from about 1 wt / wt% to about 5 wt / wt%, from about 1 wt / wt% to about 6 wt / wt%, from about 1 wt / wt% to about 7 wt / wt%, from about 1 wt / wt% to about 8 wt / wt%, from about 1 wt / wt% to about 9 wt / wt%, from about 1 wt / wt% to about 10 wt / wt%, from about 1.5 wt / wt% to about 2 wt / wt%, from about 1.5 wt / wt% to about 2.5 wt / wt%, from about 1.5 wt / wt% to about 3 wt / wt%, from about 1.5 wt / wt% to about 3.5 wt / wt%, from about 1.5 wt / wt% to about 4 wt / wt%, from about 1.5 wt / wt% to about 4.5 wt / wt%, from about 1.5 wt / wt% to about 5 wt / wt%, from about 1.5 wt / wt% to about 6 wt / wt%, from about 1.5 wt / wt% to about 7 wt / wt%, from about 1.5 wt / wt% to about 8 wt / wt%, from about 1.5 wt / wt% to about 9 wt / wt%, from about 1.5 wt / wt% to about 10 wt / wt%, from about 2 wt / wt% to about 2.5 wt / wt%, from about 2 wt / wt% to about 3 wt / wt%, from about 2 wt / wt% to about 3.5 wt / wt%, from about 2 wt / wt% to about 4 wt / wt%, from about 2 wt / wt% to about 4.5 wt / wt%, from about 2 wt / wt% to about 5 wt / wt%, from about 2 wt / wt% to about 6 wt / wt%, from about 2 wt / wt% to about 7 wt / wt%, from about 2 wt / wt% to about 8 wt / wt%, from about 2 wt / wt% to about 9 wt / wt%, from about 2 wt / wt% to about 10 wt / wt%, from about 2.5 wt / wt% to about 3 wt / wt%, from about 2.5 wt / wt% to about 3.5 wt / wt%, from about 2.5 wt / wt% to about 4 wt / wt%, from about 2.5 wt / wt% to about 4.5 wt / wt%, from about 2.5 wt / wt% to about 5 wt / wt%, from about 2.5 wt / wt% to about 6 wt / wt%, from about 2.5 wt / wt% to about 7 wt / wt%, from about 2.5 wt / wt% to about 8 wt / wt%, from about 2.5 wt / wt% to about 9 wt / wt%, from about 2.5 wt / wt% to about 10 wt / wt%, from about 3 wt / wt% to about 4 wt / wt%, from about 3 wt / wt% to about 4.5 wt / wt%, from about 3 wt / wt% to about 5wt / wt%, from about 3 wt / wt% to about 6 wt / wt%, from about 3 wt / wt% to about 7 wt / wt%, from about 3 wt / wt% to about 8 wt / wt%, from about 3 wt / wt% to about 9 wt / wt%, from about 3 wt / wt% to about 10 wt / wt%, from about 3.5 wt / wt% to about 4 wt / wt%, from about 3.5 wt / wt% to about 4.5 wt / wt%, from about 3.5 wt / wt% to about 5 wt / wt%, from about 3.5 wt / wt% to about 6 wt / wt%, from about 3.5 wt / wt% to about 7 wt / wt%, from about 3.5 wt / wt% to about 8 wt / wt%, from about 3.5 wt / wt% to about 9 wt / wt%, from about 3.5 wt / wt% to about 10 wt / wt%, from about 4 wt / wt% to about 4.5 wt / wt%, from about 4 wt / wt% to about 5 wt / wt%, from about 4 wt / wt% to about 6 wt / wt%, from about 4 wt / wt% to about 7 wt / wt%, from about 4 wt / wt% to about 8 wt / wt%, from about 4 wt / wt% to about 9 wt / wt%, from about 4 wt / wt% to about 10 wt / wt%, from about 4.5 wt / wt% to about 5 wt / wt%, from about 4.5 wt / wt% to about 6 wt / wt%, from about 4.5 wt / wt% to about 7 wt / wt%, from about 4.5 wt / wt% to about 8 wt / wt%, from about 4.5 wt / wt% to about 9 wt / wt%, from about 4.5 wt / wt% to about 10 wt / wt%, from about 5 wt / wt% to about 6 wt / wt%, from about 5 wt / wt% to about 7 wt / wt%, from about 5 wt / wt% to about 8 wt / wt%, from about 5 wt / wt% to about 9 wt / wt%, from about 5 wt / wt% to about 10 wt / wt%, from about 6 wt / wt% to about 7 wt / wt%, from about 6 wt / wt% to about 8 wt / wt%, from about 6 wt / wt% to about 9 wt / wt%, from about 6 wt / wt% to about 10 wt / wt%, from about 7 wt / wt% to about 8 wt / wt%, from about 7 wt / wt% to about 9 wt / wt%, from about 8 wt / wt% to about 10 wt / wt%, from about 8 wt / wt% to about 9 wt / wt%, from about 8 wt / wt% to about 10 wt / wt%, or from about 9 wt / wt% to about 10 wt / wt% of a Compound of the Disclosure.

[0112] In some embodiments, a Composition of the Disclosure comprises about 50 wt / wt % of a Compound of the Disclosure. In some embodiments, the composition comprises about 1 wt / wt %, about 5 wt / wt %, about 10 wt / wt %, about 15 wt / wt %, about 20 wt / wt %, about 25 wt / wt %, about 30 wt / wt %, about 35 wt / wt %, about 40 wt / wt %, about 45 wt / wt %, about 55 wt / wt %, about 60 wt / wt %, about 65 wt / wt %, about 70 wt / wt %, about 75 wt / wt %, about 80 wt / wt %, about 85 wt / wt %, about 90 wt / wt %, or about 95 wt / wt % of a Compound of the Disclosure. In some embodiments, the composition comprises about 0.1 wt / wt%, about 0.5 wt / wt%, about 1 wt / wt%, about 1.5 wt / wt%, about 2 wt / wt%, about 2.5 wt / wt%, about 3 wt / wt%, about 3.5 wt / wt%, about 4 wt / wt%, about 4.5 wt / wt%, about 5 wt / wt%, about 5.5 wt / wt%, about 6 wt / wt%, about 6.5 wt / wt%, about 7 wt / wt%, about 7.5 wt / wt%, about 8 wt / wt%, about 8.5 wt / wt%, about 9 wt / wt%, or about 10 wt / wt% of a Compound of the Disclosure.

[0113] In another embodiment, a Composition of the Disclosure comprises a Compound of the Disclosure and one or more elastomers.

[0114] The term "elastomer" as used herein is a polymer with viscoelasticity (i.e., having both viscosity and elasticity) that typically has low intermolecular forces, low Young's modulus, and high failure strain. Elastomers can typically be cross-linked by heating in the presence of one or more cross-linking agents, a process called curing or vulcanization. Rubber is one type of elastomer. Non-limiting types of rubber include natural rubber (NR), synthetic rubber, and blends thereof. The term "natural rubber" as used herein refers to a naturally occurring elastomer that can be obtained from Hevea rubber trees. Non-limiting types of synthetic rubbers include unsaturated rubbers, saturated rubbers, rubbers with fluoro and fluoralkyl or fluoralkoxy substituent groups on the polymer chain (FKM), silicone rubbers (Q), and blends thereof. Non-limiting examples of unsaturated rubbers include polyisoprene rubber (IR), butyl rubber (HR), polybutadiene rubber (BR), styrene- isoprene-butadiene rubber (SIBR), styrene butadiene rubber (SBR), nitrile butadiene rubber (NBR), chloroprene rubber (CR), ethylene propylene diene rubber (EPDM), and blends thereof. These unsaturated rubbers undergo cyclization and crosslinking reactions that lead to hardening of the aged part. As oxidation occurs, these vulcanizates harden and eventually become brittle products. Partial oxidation of vulcanizates leads to losses in performance when used in applications such as vehicle tire sidewalls. Saturated rubbers are rubbers that do not contain C=C unsaturation and include, but are not limited to, acrylic rubber (ACM), chlorinated polyethylene (CM), chlorosulfonated polyethylene (CSM), polychloromethyl oxirane (CO), ethylene-ethyl acrylate copolymer (EAM), epichlorohydrin rubber (ECO), ethylene propylene rubber (EPM), ethylenevinylacetate copolymer (EVM), rubbers with fluoro and fluoralkyl or fluoralkoxy substituent groups on the polymer chain (FKM), silicone rubber (Q), and blends thereof.

[0115] In some embodiments, the natural rubber comprises rubber derived from an alternative rubber plant. The term "natural rubber comprises rubber derived from an alternative rubber plant" as used herein refers to a naturally occurring elastomer that can be obtained from "non-Hevea" sources. In some embodiments, the alternative rubber plant is Parthenium argentatum (guayule) or Taraxacum kok-saghyz (Russian dandelion).

[0116] In some embodiments, the one or more elastomers further comprises recycled rubber. The term "recycled rubber" as used herein refers to an elastomer that has been reclaimed from scrap materials such as used tires.

[0117] In some embodiments, a Composition of the Disclosure comprises from about 15 wt / wt % to about 100 wt / wt % of one or more elastomers. In some embodiments, the composition comprises from about 1 wt / wt % to about 5 wt / wt %, from about 1 wt / wt % to about 15 wt / wt %, from about 1 wt / wt % to about 25 wt / wt %, from about 1 wt / wt % to about 35 wt / wt %, from about 1 wt / wt % to about 45 wt / wt %, from about 1 wt / wt % to about 55 wt / wt %, from about 1 wt / wt % to about 65 wt / wt %, from about 1 wt / wt % to about 75 wt / wt %, from about 1 wt / wt % to about 85 wt / wt %, from about 1 wt / wt % to about 95 wt / wt %, from about 1 wt / wt % to about 100 wt / wt %, from about 5 wt / wt % to about 15 wt / wt %, from about 5 wt / wt % to about 25 wt / wt %, from about 5 wt / wt % to about 35 wt / wt %, from about 5 wt / wt % to about 45 wt / wt %, from about 5 wt / wt % to about 55 wt / wt %, from about 5 wt / wt % to about 65 wt / wt %, from about 5 wt / wt % to about 75 wt / wt %, from about 5 wt / wt % to about 85 wt / wt %, from about 5 wt / wt % to about 95 wt / wt %, from about 5 wt / wt % to about 100 wt / wt %, from about 15 wt / wt % to about 25 wt / wt %, from about 15 wt / wt % to about 35 wt / wt %, from about 15 wt / wt % to about 45 wt / wt %, from about 15 wt / wt % to about 55 wt / wt %, from about 15 wt / wt % to about 65 wt / wt %, from about 15 wt / wt % to about 75 wt / wt %, from about 15 wt / wt % to about 95 wt / wt %, from about 15 wt / wt % to about 100 wt / wt %, from about 25 wt / wt % to about 35 wt / wt %, from about 25 wt / wt % to about 45 wt / wt %, from about 25 wt / wt % to about 55 wt / wt %, from about 25 wt / wt % to about 65 wt / wt %, from about 25 wt / wt % to about 75 wt / wt %, from about 25 wt / wt % to about 85 wt / wt %, from about 25 wt / wt % to about 95 wt / wt %, from about 25 wt / wt % to about 100 wt / wt %, from about 35 wt / wt % to about 45 wt / wt %, from about 35 wt / wt % to about 55 wt / wt %, from about 35 wt / wt % to about 65 wt / wt %, from about 35 wt / wt % to about 75 wt / wt %, from about 35 wt / wt % to about 85 wt / wt %, from about 35 wt / wt % to about 95 wt / wt %, from about 35 wt / wt % to about 100 wt / wt %, from about 45 wt / wt % to about 55 wt / wt %, from about 45 wt / wt % to about 65 wt / wt %, from about 45 wt / wt % to about 75 wt / wt %, from about 45 wt / wt % to about 85 wt / wt %, from about 45 wt / wt % to about 95 wt / wt %, from about 45 wt / wt % to about 100 wt / wt %, from about 55 wt / wt % to about 65 wt / wt %, from about 55 wt / wt % to about 75 wt / wt %, from about 55 wt / wt % to about 85 wt / wt %, from about 55 wt / wt % to about 95 wt / wt %, from about 55 wt / wt % to about 100 wt / wt %, from about 65 wt / wt % to about 75 wt / wt %, from about 65 wt / wt % to about 85 wt / wt %, from about 65 wt / wt % to about 95 wt / wt %, from about 65 wt / wt % to about 100 wt / wt %, from about 75 wt / wt % to about 85 wt / wt %, from about 75 wt / wt % to about 95 wt / wt %, from about 75 wt / wt% to about 100 wt / wt %, from about 85 wt / wt % to about 95 wt / wt %, or from about 95 wt / wt % to about 100 wt / wt % of one or more elastomers.

[0118] In some embodiments, a Composition of the Disclosure comprises about 50 wt / wt % of one or more elastomers. In some embodiments, the composition comprises about 1 wt / wt %, about 5 wt / wt %, about 10 wt / wt %, about 15 wt / wt %, about 20 wt / wt %, about 25 wt / wt %, about 30 wt / wt %, about 35 wt / wt %, about 40 wt / wt %, about 45 wt / wt %, about 55 wt / wt %, about 60 wt / wt %, about 65 wt / wt %, about 70 wt / wt %, about 75 wt / wt %, about 80 wt / wt %, about 85 wt / wt %, about 90 wt / wt %, about 95 wt / wt %, or about 100 wt / wt% of one or more elastomers.

[0119] The term "phr" as used herein refers to parts per hundred parts of rubber by weight.The parts by weight of individual components are based on 100 parts by weight of the total mass of the one or more elastomers present in the composition.

[0120] In some embodiments, a Composition of the Disclosure comprises from about 1 phr to about 5 phr of a Compound of the Disclosure. In some embodiments, the composition comprises from about 0.01 phr to about 0.1 phr, from about 0.01 phr to about 0.5 phr, from about 0.01 phr to about 1 phr, from about 0.01 phr to about 2 phr, from about 0.01 phr to about 3 phr, from about 0.01 phr to about 4 phr, from about 0.01 phr to about 5 phr, from about 0.01 phr to about 7.5 phr, from about 0.01 phr to about 10 phr, from about 0.01 phr to about 20 phr, from about 0.1 phr to about 0.5 phr, from about 0.1 phr to about 1 phr, from about 0.1 phr to about 2 phr, from about 0.1 phr to about 3 phr, from about 0.1 phr to about 4 phr, from about 0.1 phr to about 5 phr, from about 0.1 phr to about 7.5 phr, from about 0.1 phr to about 10 phr, from about 0.1 phr to about 20 phr, from about 1 phr to about 2 phr, from about 1 phr to about 3 phr, from about 1 phr to about 4 phr, from about 1 phr to about 7.5 phr, from about 1 phr to about 10 phr, from about 1 phr to about 20 phr, from about 2 phr to about 3 phr, from about 2 phr to about 4 phr, from about 2 phr to about 5 phr, from about 2 phr to about 7.5 phr, from about 2 phr to about 10 phr, from about 2 phr to about 20 phr, from about 3 phr to about 4 phr, from about 3 phr to about 5 phr, from about 3 phr to about 7.5 phr, from about 3 phr to about 10 phr, from about 3 phr to about 20 phr, from about 4 phr to about 5 phr, from about 4 phr to about 7.5 phr, from about 4 phr to about 10 phr, from about 4 phr to about 20 phr, from about 5 phr to about 7.5 phr, from about 5 phr to about 10 phr, from about 5 phr to about 20 phr, from about 7.5 phr to about 10 phr, from about 7.5 phr to about 20 phr, or from about 10 phr to about 20 phr of a Compound of the Disclosure.

[0121] In some embodiments, a Composition of the Disclosure comprises about 3 phr of a Compound of the Disclosure. In some embodiments, the composition comprises about 0.01 phr, about 0.1 phr, about 0.5 phr, about 1 phr, about 2 phr, about 3 phr, about 4 phr, about 5 phr, about 7.5 phr, about 10 phr, or about 20 phr of a Compound of the Disclosure.

[0122] In some embodiments, a Composition of the Disclosure comprises a Compound of the Disclosure and one or more fillers.

[0123] The term "filler" as used herein is a substance that reinforces an elastomeric composition or gives an elastomeric composition other properties, including but not limited to expanding the volume of the composition. Non-limiting examples of fillers include carbon black, silica, kaolin, calcium silicate, talc, carbon nanotubes (CNT), carbon fibers (HCF), graphite, graphenes, aluminosilicates, starch, and fibers, and combinations thereof.

[0124] In some embodiments, the filler is derived from natural sources. For example, silica may be derived from rice husks.

[0125] In some embodiments, a Composition of the Disclosure comprises from about 15 wt / wt % to about 85 wt / wt % of one or more fillers. In some embodiments, the composition comprises from about 1 wt / wt % to about 5 wt / wt %, from about 1 wt / wt % to about 15 wt / wt %, from about 1 wt / wt % to about 25 wt / wt %, from about 1 wt / wt % to about 35 wt / wt %, from about 1 wt / wt % to about 45 wt / wt %, from about 1 wt / wt % to about 55 wt / wt %, from about 1 wt / wt % to about 65 wt / wt %, from about 1 wt / wt % to about 75 wt / wt %, from about 1 wt / wt % to about 85 wt / wt %, from about 1 wt / wt % to about 95 wt / wt %, from about 5 wt / wt % to about 15 wt / wt %, from about 5 wt / wt % to about 25 wt / wt %, from about 5 wt / wt % to about 35 wt / wt %, from about 5 wt / wt % to about 45 wt / wt %, from about 5 wt / wt % to about 55 wt / wt %, from about 5 wt / wt % to about 65 wt / wt %, from about 5 wt / wt % to about 75 wt / wt %, from about 5 wt / wt % to about 85 wt / wt %, from about 5 wt / wt % to about 95 wt / wt %, from about 15 wt / wt % to about 25 wt / wt %, from about 15 wt / wt % to about 35 wt / wt %, from about 15 wt / wt % to about 45 wt / wt %, from about 15 wt / wt % to about 55 wt / wt %, from about 15 wt / wt % to about 65 wt / wt %, from about 15 wt / wt % to about 75 wt / wt %, from about 15 wt / wt % to about 95 wt / wt %, from about 25 wt / wt % to about 35 wt / wt %, from about 25 wt / wt % to about 45 wt / wt %, from about 25 wt / wt % to about 55 wt / wt %, from about 25 wt / wt % to about 65 wt / wt %, from about 25 wt / wt % to about 75 wt / wt %, from about 25 wt / wt % to about 85 wt / wt %, from about 25 wt / wt % to about 95 wt / wt %, from about 35 wt / wt % to about 45 wt / wt %, from about 35 wt / wt % to about 55 wt / wt %, from about 35 wt / wt % toabout 65 wt / wt %, from about 35 wt / wt % to about 75 wt / wt %, from about 35 wt / wt % to about 85 wt / wt %, from about 35 wt / wt % to about 95 wt / wt %, from about 45 wt / wt % to about 55 wt / wt %, from about 45 wt / wt % to about 65 wt / wt %, from about 45 wt / wt % to about 75 wt / wt %, from about 45 wt / wt % to about 85 wt / wt %, from about 45 wt / wt % to about 95 wt / wt %, from about 55 wt / wt % to about 65 wt / wt %, from about 55 wt / wt % to about 75 wt / wt %, from about 55 wt / wt % to about 85 wt / wt %, from about 55 wt / wt % to about 95 wt / wt %, from about 65 wt / wt % to about 75 wt / wt %, from about 65 wt / wt % to about 85 wt / wt %, from about 65 wt / wt % to about 95 wt / wt %, from about 75 wt / wt % to about 85 wt / wt %, from about 75 wt / wt % to about 95 wt / wt %, or from about 85 wt / wt % to about 95 wt / wt % of one or more fillers.

[0126] In some embodiments, a Composition of the Disclosure comprises about 50 wt / wt % of one or more fillers. In some embodiments, the composition comprises about 1 wt / wt %, about 5 wt / wt %, about 10 wt / wt %, about 15 wt / wt %, about 20 wt / wt %, about 25 wt / wt %, about 30 wt / wt %, about 35 wt / wt %, about 40 wt / wt %, about 45 wt / wt %, about 55 wt / wt %, about 60 wt / wt %, about 65 wt / wt %, about 70 wt / wt %, about 75 wt / wt %, about 80 wt / wt %, about 85 wt / wt %, about 90 wt / wt %, or about 95 wt / wt % of one or more fillers.

[0127] In some embodiments, a Composition of the Disclosure comprises from about 30 phr to about 500 phr of one or more fillers. In some embodiments, the composition comprises from about 30 phr to about 50 phr, from about 30 phr to about 100 phr, from about 30 phr to about 150 phr, from about 30 phr to about 200 phr, from about 30 phr to about 250 phr, from about 30 phr to about 300 phr, from about 30 phr to about 350 phr, from about 30 phr to about 400 phr, from about 30 phr to about 450 phr, from about 30 phr to about 500 phr, from about 50 phr to about 100 phr, from about 50 phr to about 150 phr, from about 50 phr to about 200 phr, from about 50 phr to about 250 phr, from about 50 phr to about 300 phr, from about 50 phr to about 350 phr, from about 50 phr to about 400 phr, from about 50 phr to about 450 phr, from about 50 phr to about 500 phr, from about 100 phr to about 150 phr, from about 100 phr to about 200 phr, from about 100 phr to about 250 phr, from about 100 phr to about 300 phr, from about 100 phr to about 350 phr, from about 100 phr to about 400 phr, from about 100 phr to about 450 phr, from about 100 phr to about 500 phr, from about 150 phr to about 200 phr, from about 150 phr to about 250 phr, from about 150 phr to about 300 phr, from about 150 phr to about 350 phr, from about 150 phr to about 400 phr, from about 150 phr to about 450 phr, from about 150 phr to about500 phr, from about 200 phr to about 250 phr, from about 200 phr to about 300 phr, from about 200 phr to about 350 phr, from about 200 phr to about 400 phr, from about 200 phr to about 450 phr, from about 200 phr to about 500 phr, from about 250 phr to about 300 phr, from about 250 phr to about 350 phr, from about 250 phr to about 400 phr, from about 250 phr to about 450 phr, from about 250 phr to about 500 phr, from about 300 phr to about 350 phr, from about 300 phr to about 400 phr, from about 300 phr to about 450 phr, from about 300 phr to about 500 phr, from about 350 phr to about 400 phr, from about 350 phr to about 450 phr, from about 350 phr to about 500 phr, from about 400 phr to about 450 phr, from about 400 phr to about 500 phr, or from about 450 phr to about 500 phr of one or more fillers.

[0128] In some embodiments, a Composition of the Disclosure comprises about 300 phr of one or more fillers. In some embodiments, the composition comprises about 30 phr, about 50 phr, about 100 phr, about 150 phr, about 200 phr, about 250 phr, about 350 phr, about 400 phr, about 450 phr, or about 500 phr of one or more fillers.

[0129] In some embodiments, a Composition of the Disclosure comprises a Compound of the Disclosure and one or more rubber chemicals. The term "rubber chemicals" as used herein refers to a compound or substance used to facilitate the vulcanization of rubber. Rubber chemicals include, but are not limited to, vulcanizing agents, accelerators, activators, and pre-vulcanization inhibitors.

[0130] The term "vulcanization" as used herein refers to a process wherein cross-links are formed between elastomers to effect changes in the material properties of elastomers. In particular, vulcanization typically increases the rigidity and durability of elastomers. Vulcanization is carried out at room temperature or at elevated temperatures, depending on the nature of the elastomer(s), filler(s), and rubber chemical(s) being used. The term "curing" is also used in the art to describe this process.

[0131] The term "vulcanizing agent" as used herein refers to any substance that enables cross-linking between elastomers. Vulcanizing agents can enable cross-linking between separate polymer chains of an elastomer by various mechanisms, including, but not limited to, by formation of covalent bonds between the vulcanizing agent and two or more separate polymer chains or by generating radical species on separate polymer chains that can combine to form covalent bonds between the two polymer chains. Non-limiting examples of vulcanizing agents include sulfur, peroxides, vulcanized vegetable oil, factices and resins. Non-limiting examples of sulfur include octasulfur (Ss), cyclododecasulfur (S12),and polymeric sulfur. Non-limiting examples of peroxides include benzoyl peroxide, dicumyl peroxide (DC), 2,5-dimethyl-2,5-di-(tert-butylperoxy)-3-hexyne (2,5 Tri), 2,5- dimethyl-2,5-di(tert-butylperoxy)hexane (DDPH), di-(2-tert- butylperoxyisopropyl)benzene (VC), butyl-4,4-di-(tert-butylperoxy)valerate (VAL), and l,l-di(tert-butylperoxy)-3,3,5-trimethylcyclohexane (TMC). Nonlimiting examples of resins include bonding resins. The term "bonding resin" as used herein refers to a chemical such as resorcinol formaldehyde resins and phenolic resins that reacts with methylene donors (such as hexamethylenetetramine (HMTA) or hexamethoxymethyl melamine (HMMM)) to promote adhesion.

[0132] The term "accelerator" as used herein refers to any substance that increases the kinetics of vulcanization. In some embodiments, accelerators enable vulcanization to be performed at lower temperatures and / or to use the vulcanization agent, e.g., sulfur, more efficiently. Non-limiting examples of accelerators include guanidines, thiazoles, sulfenamides, thiurams, dithiocarbamates, xanthates, and thiophosphates. Non-limiting examples of guanidines include diphenylguanidine (DPG). Non-limiting examples of thiazoles include 2-mercaptobenzothiazole (MBT), zinc 2-mercaptobenzothiazole (ZMBT), mercaptobenzothiazole disulfide (MBTS), and V- / ert-butyl-2-benzothi azole sulfenimide (TBSI). Non-limiting examples of sulfenamides include V- / c / 7-butyl-2- benzothiazylsulfenamide (TBBS), V-cyclohexylbenzothiazol-2-sulfenamide (CBS), dicyclohexyl-2-benzothiazolesulfenamide (DCBS), 7V-oxy di ethylene benzothiazole sulfenamide (OBTS), V-oxy di ethylenethiocarbamyl-V'-oxy di ethylene sulfenamide (OTOS), and thiocarbamyl sulfenamide. Non-limiting examples of thiurams include dimethylcarbamothioic dithioperoxyanhydride (thiram), dipentamethylene thiuram tetrasulfide (DPIT), tetrabenzyl thiuram disulfide (TBzTD), tetraethylthiuram disulfide (TETD), tetramethylthiuram disulfide (TMTD), and tetramethylthiuram monosulfide (TMTM). Non-limiting examples of dithiocarbamates include zinc dimethyldithiocarbamate (ZDMC), zinc diethyldithiocarbamate (ZDEC), zinc dibutyldithiocarbamate (ZDBC), nickel dibutyldithiocarbamate (NDBC), sodium dibenzyldithiocarbamate (SBEC), sodium di ethyl di thiocarbamate (SDEC), tellurium diethyldithiocarbamate (TDEC), and zinc dibenzyldithiocarbamate (ZEBC).

[0133] The term "activator" as used herein refers to any substance that activates a vulcanizing agent and enables it to cross-link elastomers as described above. Activators may act via various mechanisms, including, but not limited to, by forming chemicalcomplexes with accelerators or by coordinating to sulfur (when sulfur is used as a vulcanizing agent). Non-limiting examples of activators include metal oxides, acids, and metal complexex. Non-limiting examples of metal oxides include zinc oxide, magnesium oxide, and lead oxide. Non-limiting examples of acids include stearic acid and lauric acid. Non limiting examples of metal complexes include zinc ethylhexanoate.

[0134] The term "pre-vulcanization inhibitor" as used herein refers to compounds that delay the onset and / or the rate of vulcanization. These compounds are also referred to as "retarders." Non-limiting examples of pre-vulcanization inhibitors include N- (cyclohexylthio)phthalimide (CTP), benzoic anhydride, salicylic anhydride, and phthalic anhydride.

[0135] In some embodiments, a Composition of the Disclosure comprises from about 15 wt / wt % to about 85 wt / wt % of one or more rubber chemicals. In some embodiments, the composition comprises from about 1 wt / wt % to about 5 wt / wt %, from about 1 wt / wt % to about 15 wt / wt %, from about 1 wt / wt % to about 25 wt / wt %, from about 1 wt / wt % to about 35 wt / wt %, from about 1 wt / wt % to about 45 wt / wt %, from about 1 wt / wt % to about 55 wt / wt %, from about 1 wt / wt % to about 65 wt / wt %, from about 1 wt / wt % to about 75 wt / wt %, from about 1 wt / wt % to about 85 wt / wt %, from about 1 wt / wt % to about 95 wt / wt %, from about 5 wt / wt % to about 15 wt / wt %, from about 5 wt / wt % to about 25 wt / wt %, from about 5 wt / wt % to about 35 wt / wt %, from about 5 wt / wt % to about 45 wt / wt %, from about 5 wt / wt % to about 55 wt / wt %, from about 5 wt / wt % to about 65 wt / wt %, from about 5 wt / wt % to about 75 wt / wt %, from about 5 wt / wt % to about 85 wt / wt %, from about 5 wt / wt % to about 95 wt / wt %, from about 15 wt / wt % to about 25 wt / wt %, from about 15 wt / wt % to about 35 wt / wt %, from about 15 wt / wt % to about 45 wt / wt %, from about 15 wt / wt % to about 55 wt / wt %, from about 15 wt / wt % to about 65 wt / wt %, from about 15 wt / wt % to about 75 wt / wt %, from about 15 wt / wt % to about 95 wt / wt %, from about 25 wt / wt % to about 35 wt / wt %, from about 25 wt / wt % to about 45 wt / wt %, from about 25 wt / wt % to about 55 wt / wt %, from about 25 wt / wt % to about 65 wt / wt %, from about 25 wt / wt % to about 75 wt / wt %, from about 25 wt / wt % to about 85 wt / wt %, from about 25 wt / wt % to about 95 wt / wt %, from about 35 wt / wt % to about 45 wt / wt %, from about 35 wt / wt % to about 55 wt / wt %, from about 35 wt / wt % to about 65 wt / wt %, from about 35 wt / wt % to about 75 wt / wt %, from about 35 wt / wt % to about 85 wt / wt %, from about 35 wt / wt % to about 95 wt / wt %, from about 45 wt / wt % to about 55 wt / wt %, from about 45 wt / wt % to about 65 wt / wt %, from about 45 wt / wt % toabout 75 wt / wt %, from about 45 wt / wt % to about 85 wt / wt %, from about 45 wt / wt % to about 95 wt / wt %, from about 55 wt / wt % to about 65 wt / wt %, from about 55 wt / wt % to about 75 wt / wt %, from about 55 wt / wt % to about 85 wt / wt %, from about 55 wt / wt % to about 95 wt / wt %, from about 65 wt / wt % to about 75 wt / wt %, from about 65 wt / wt % to about 85 wt / wt %, from about 65 wt / wt % to about 95 wt / wt %, from about 75 wt / wt % to about 85 wt / wt %, from about 75 wt / wt % to about 95 wt / wt %, or from about 85 wt / wt % to about 95 wt / wt % of one or more rubber chemicals.

[0136] In some embodiments, a Composition of the Disclosure comprises about 15 wt / wt % of one or more rubber chemicals. In some embodiments, the composition comprises about 1 wt / wt %, about 5 wt / wt %, about 10 wt / wt %, about 20 wt / wt %, about 25 wt / wt %, about 30 wt / wt %, about 35 wt / wt %, about 40 wt / wt %, about 45 wt / wt %, about 50 wt / wt %, about 55 wt / wt %, about 60 wt / wt %, about 65 wt / wt %, about 70 wt / wt %, about 75 wt / wt %, about 80 wt / wt %, about 85 wt / wt %, about 90 wt / wt %, or about 95 wt / wt % of one or more rubber chemicals.

[0137] In some embodiments, a Composition of the Disclosure comprises from about 1 phr to about 20 phr of one or more rubber chemicals. In some embodiments, the composition comprises from about 0.1 phr to about 1 phr, from about 0.1 phr to about 5 phr, from about 0.1 phr to about 10 phr, from about 0.1 phr to about 15 phr, from about 0.1 phr to about 20 phr, from about 0.1 phr to about 25 phr, from about 0.1 phr to about 30 phr, from about 0.1 phr to about 35 phr, from about 0.1 phr to about 40 phr, from about 1 phr to about 5 phr, from about 1 phr to about 10 phr, from about 1 phr to about 15 phr, from about 1 phr to about 25 phr, from about 1 phr to about 30 phr, from about 1 phr to about 35 phr, from about 1 phr to about 40 phr, from about 5 phr to about 10 phr, from about 5 phr to about 15 phr, from about 5 phr to about 20 phr, from about 5 phr to about 25 phr, from about 5 phr to about 30 phr, from about 5 phr to about 35 phr, from about 5 phr to about 40 phr, from about 10 phr to about 15 phr, from about 10 phr to about 20 phr, from about 10 phr to about 25 phr, from about 10 phr to about 30 phr, from about 10 phr to about 35 phr, from about 10 phr to about 40 phr, from about 15 phr to about 20 phr, from about 15 phr to about 25 phr, from about 15 phr to about 30 phr, from about 15 phr to about 35 phr, from about 15 phr to about 40 phr, from about 20 phr to about 25 phr, from about 20 phr to about 30 phr, from about 20 phr to about 35 phr, from about 20 phr to about 40 phr, from about 25 phr to about 30 phr, from about 25 phr to about 35 phr, from about 25 phr to about 40 phr, fromabout 30 phr to about 35 phr, from about 30 phr to about 40 phr, or from about 35 phr to about 40 phr of one or more rubber chemicals.

[0138] In some embodiments, a Composition of the Disclosure comprises about 10 phr of one or more rubber chemicals. In some embodiments, the composition comprises about 0.1 phr, about 1 phr, about 5 phr, about 15 phr, about 20 phr, about 25 phr, about 30 phr, about 35 phr, or about 40 phr of one or more rubber chemicals.

[0139] The term "plasticizer" as used herein refers to a processing aid used to reduce the viscosity, increase the plasticity, and / or extend the volume of a composition. Plasticizers facilitate the process of mixing and forming a composition comprising an elastomer before the composition is vulcanized. Non-limiting examples of plasticizers include mineral oils (paraffinic, aromatic, or naphthenic), organic esters, resins, waxes, ester plasticizers, and naturally derived oils, such as soybean oil, vegetable oil, or orange oil.

[0140] In some embodiments, a Composition of the Disclosure comprises from about 15 wt / wt % to about 85 wt / wt % of one or more plasticizers. In some embodiments, the composition comprises from about 1 wt / wt % to about 5 wt / wt %, from about 1 wt / wt % to about 15 wt / wt %, from about 1 wt / wt % to about 25 wt / wt %, from about 1 wt / wt % to about 35 wt / wt %, from about 1 wt / wt % to about 45 wt / wt %, from about 1 wt / wt % to about 55 wt / wt %, from about 1 wt / wt % to about 65 wt / wt %, from about 1 wt / wt % to about 75 wt / wt %, from about 1 wt / wt % to about 85 wt / wt %, from about 1 wt / wt % to about 95 wt / wt %, from about 5 wt / wt % to about 15 wt / wt %, from about 5 wt / wt % to about 25 wt / wt %, from about 5 wt / wt % to about 35 wt / wt %, from about 5 wt / wt % to about 45 wt / wt %, from about 5 wt / wt % to about 55 wt / wt %, from about 5 wt / wt % to about 65 wt / wt %, from about 5 wt / wt % to about 75 wt / wt %, from about 5 wt / wt % to about 85 wt / wt %, from about 5 wt / wt % to about 95 wt / wt %, from about 15 wt / wt % to about 25 wt / wt %, from about 15 wt / wt % to about 35 wt / wt %, from about 15 wt / wt % to about 45 wt / wt %, from about 15 wt / wt % to about 55 wt / wt %, from about 15 wt / wt % to about 65 wt / wt %, from about 15 wt / wt % to about 75 wt / wt %, from about 15 wt / wt % to about 95 wt / wt %, from about 25 wt / wt % to about 35 wt / wt %, from about 25 wt / wt % to about 45 wt / wt %, from about 25 wt / wt % to about 55 wt / wt %, from about 25 wt / wt % to about 65 wt / wt %, from about 25 wt / wt % to about 75 wt / wt %, from about 25 wt / wt % to about 85 wt / wt %, from about 25 wt / wt % to about 95 wt / wt %, from about 35 wt / wt % to about 45 wt / wt %, from about 35 wt / wt % to about 55 wt / wt %, from about 35 wt / wt % to about 65 wt / wt %, from about 35 wt / wt % to about 75 wt / wt %, from about 35 wt / wt % toabout 85 wt / wt %, from about 35 wt / wt % to about 95 wt / wt %, from about 45 wt / wt % to about 55 wt / wt %, from about 45 wt / wt % to about 65 wt / wt %, from about 45 wt / wt % to about 75 wt / wt %, from about 45 wt / wt % to about 85 wt / wt %, from about 45 wt / wt % to about 95 wt / wt %, from about 55 wt / wt % to about 65 wt / wt %, from about 55 wt / wt % to about 75 wt / wt %, from about 55 wt / wt % to about 85 wt / wt %, from about 55 wt / wt % to about 95 wt / wt %, from about 65 wt / wt % to about 75 wt / wt %, from about 65 wt / wt % to about 85 wt / wt %, from about 65 wt / wt % to about 95 wt / wt %, from about 75 wt / wt % to about 85 wt / wt %, from about 75 wt / wt % to about 95 wt / wt %, or from about 85 wt / wt % to about 95 wt / wt % of one or more plasticizers.

[0141] In some embodiments, a Composition of the Disclosure comprises about 15 wt / wt % of one or more plasticizers. In some embodiments, the composition comprises about 1 wt / wt %, about 5 wt / wt %, about 10 wt / wt %, about 20 wt / wt %, about 25 wt / wt %, about 30 wt / wt %, about 35 wt / wt %, about 40 wt / wt %, about 45 wt / wt %, about 50 wt / wt %, about 55 wt / wt %, about 60 wt / wt %, about 65 wt / wt %, about 70 wt / wt %, about 75 wt / wt %, about 80 wt / wt %, about 85 wt / wt %, about 90 wt / wt %, or about 95 wt / wt % of one or more plasticizers.

[0142] In some embodiments, a Composition of the Disclosure comprises from about 1 phr to about 20 phr of one or more plasticizers. In some embodiments, the composition comprises from about 0.1 phr to about 1 phr, from about 0.1 phr to about 5 phr, from about 0.1 phr to about 10 phr, from about 0.1 phr to about 15 phr, from about 0.1 phr to about 20 phr, from about 0.1 phr to about 25 phr, from about 0.1 phr to about 30 phr, from about 0.1 phr to about 35 phr, from about 0.1 phr to about 40 phr, from about 1 phr to about 5 phr, from about 1 phr to about 10 phr, from about 1 phr to about 15 phr, from about 1 phr to about 25 phr, from about 1 phr to about 30 phr, from about 1 phr to about 35 phr, from about 1 phr to about 40 phr, from about 5 phr to about 10 phr, from about 5 phr to about 15 phr, from about 5 phr to about 20 phr, from about 5 phr to about 25 phr, from about 5 phr to about 30 phr, from about 5 phr to about 35 phr, from about 5 phr to about 40 phr, from about 10 phr to about 15 phr, from about 10 phr to about 20 phr, from about 10 phr to about 25 phr, from about 10 phr to about 30 phr, from about 10 phr to about 35 phr, from about 10 phr to about 40 phr, from about 15 phr to about 20 phr, from about 15 phr to about 25 phr, from about 15 phr to about 30 phr, from about 15 phr to about 35 phr, from about 15 phr to about 40 phr, from about 20 phr to about 25 phr, from about 20 phr to about 30 phr, from about 20 phr to about 35 phr, from about 20 phr to about 40 phr, from about 25 phr toabout 30 phr, from about 25 phr to about 35 phr, from about 25 phr to about 40 phr, from about 30 phr to about 35 phr, from about 30 phr to about 40 phr, or from about 35 phr to about 40 phr of one or more plasticizers.

[0143] In some embodiments, a Composition of the Disclosure comprises about 10 phr of one or more plasticizers. In some embodiments, the composition comprises about 0.1 phr, about 1 phr, about 5 phr, about 15 phr, about 20 phr, about 25 phr, about 30 phr, about 35 phr, or about 40 phr of one or more plasticizers.

[0144] In some embodiments, a Composition of the Disclosure further comprises one or more additional anti degradants that is (are) not a Compound of the Disclosure.

[0145] In some embodiments, the one of the additional anti degradants is an antioxidant. In some embodiments, the one of the additional anti degradants is an antiozonant. Nonlimiting examples of anti degradants include paraphenylenediamines (PPDs), trimethyldihydroquinolines (TMQs), phenolics, alkylated diphenylamines (DP As), diphenylamineketone condensates, and natural antidegradants. Non-limiting examples of PPDs include N1-(4-m ethyl pentan-2-yl )-A4-phenylbenzene- 1 ,4-diamine (6PPD), N-( 1 ,4- dimethylpentyl)-A-phenyl-p-phenylenediamine (7PPD), 7V1-phenyl-A4-(propan-2- yl)benzene-l,4-diamine (IPPD), A,A'-di- ec-butyl- / ?-phenylenediamine (44PD), N,N'~ bis(l,3-dimethylbutyl)-p-phenylenediamine (66PD), 7V,A-bis(l,4-dimethylpentyl)-p- phenylenediamine (77PD), and A-ZC-dioctyl- -phenylenediamine (88PD). Non-limiting examples of TMQs include 2,2,4-trimethyl-l,2-dihydroquinoline and oligomers or polymers thereof.

[0146] In some embodiments, a Composition of the Disclosure comprises from about 15 wt / wt % to about 85 wt / wt % of one or more additional anti degradants. In some embodiments, the composition comprises from about 1 wt / wt % to about 5 wt / wt %, from about 1 wt / wt % to about 15 wt / wt %, from about 1 wt / wt % to about 25 wt / wt %, from about 1 wt / wt % to about 35 wt / wt %, from about 1 wt / wt % to about 45 wt / wt %, from about 1 wt / wt % to about 55 wt / wt %, from about 1 wt / wt % to about 65 wt / wt %, from about 1 wt / wt % to about 75 wt / wt %, from about 1 wt / wt % to about 85 wt / wt %, from about 1 wt / wt % to about 95 wt / wt %, from about 5 wt / wt % to about 15 wt / wt %, from about 5 wt / wt % to about 25 wt / wt %, from about 5 wt / wt % to about 35 wt / wt %, from about 5 wt / wt % to about 45 wt / wt %, from about 5 wt / wt % to about 55 wt / wt %, from about 5 wt / wt % to about 65 wt / wt %, from about 5 wt / wt % to about 75 wt / wt %, from about 5 wt / wt % to about 85 wt / wt %, from about 5 wt / wt % to about 95 wt / wt %, fromabout 15 wt / wt % to about 25 wt / wt %, from about 15 wt / wt % to about 35 wt / wt %, from about 15 wt / wt % to about 45 wt / wt %, from about 15 wt / wt % to about 55 wt / wt %, from about 15 wt / wt % to about 65 wt / wt %, from about 15 wt / wt % to about 75 wt / wt %, from about 15 wt / wt % to about 95 wt / wt %, from about 25 wt / wt % to about 35 wt / wt %, from about 25 wt / wt % to about 45 wt / wt %, from about 25 wt / wt % to about 55 wt / wt %, from about 25 wt / wt % to about 65 wt / wt %, from about 25 wt / wt % to about 75 wt / wt %, from about 25 wt / wt % to about 85 wt / wt %, from about 25 wt / wt % to about 95 wt / wt %, from about 35 wt / wt % to about 45 wt / wt %, from about 35 wt / wt % to about 55 wt / wt %, from about 35 wt / wt % to about 65 wt / wt %, from about 35 wt / wt % to about 75 wt / wt %, from about 35 wt / wt % to about 85 wt / wt %, from about 35 wt / wt % to about 95 wt / wt %, from about 45 wt / wt % to about 55 wt / wt %, from about 45 wt / wt % to about 65 wt / wt %, from about 45 wt / wt % to about 75 wt / wt %, from about 45 wt / wt % to about 85 wt / wt %, from about 45 wt / wt % to about 95 wt / wt %, from about 55 wt / wt % to about 65 wt / wt %, from about 55 wt / wt % to about 75 wt / wt %, from about 55 wt / wt % to about 85 wt / wt %, from about 55 wt / wt % to about 95 wt / wt %, from about 65 wt / wt % to about 75 wt / wt %, from about 65 wt / wt % to about 85 wt / wt %, from about 65 wt / wt % to about 95 wt / wt %, from about 75 wt / wt % to about 85 wt / wt %, from about 75 wt / wt % to about 95 wt / wt %, or from about 85 wt / wt % to about 95 wt / wt % of one or more additional anti degradants.

[0147] In some embodiments, a Composition of the Disclosure comprises about 15 wt / wt % of one or more additional anti degradants. In some embodiments, the composition comprises about 1 wt / wt %, about 5 wt / wt %, about 10 wt / wt %, about 20 wt / wt %, about 25 wt / wt %, about 30 wt / wt %, about 35 wt / wt %, about 40 wt / wt %, about 45 wt / wt %, about 50 wt / wt %, about 55 wt / wt %, about 60 wt / wt %, about 65 wt / wt %, about 70 wt / wt %, about 75 wt / wt %, about 80 wt / wt %, about 85 wt / wt %, about 90 wt / wt %, or about 95 wt / wt % of one or more additional anti degradants.

[0148] In some embodiments, a Composition of the Disclosure comprises from about 1 to about 5 phr of one or more additional anti degradants. In some embodiments, the composition comprises from about 0.001 phr to about 0.01 phr, from about 0.001 phr to about 0.1 phr, from about 0.001 phr to about 1 phr, from about 0.001 phr to about 5 phr, from about 0.001 phr to about 7.5 phr, from about 0.001 phr to about 10 phr, from about 0.01 phr to about 0.1 phr, from about 0.01 phr to about 1 phr, from about 0.01 phr to about 5 phr, from about 0.01 phr to about 7.5 phr, from about 0.01 phr to about 10 phr, from about 0.1 phr to about 1 phr, from about 0.1 phr to about 5 phr, from about 0.1 phr to about 7.5phr, from about 0.1 phr to about 10 phr, from about 1 phr to about 7.5 phr, from about 1 phr to about 10 phr, from about 5 phr to about 7.5 phr, from about 5 phr to about 10 phr, or from about 7.5 phr to about 10 phr of one or more additional anti degradants.

[0149] In some embodiments, a Composition of the Disclosure comprises about 3 phr of one or more additional anti degradants. In some embodiments, the composition comprises about 0.001 phr, about 0.01 phr, about 0.1 phr, about 1 phr, about 2 phr, about 4 phr, about 5 phr, about 7.5 phr, or about 10 phr of one or more additional anti degradants.

[0150] In some embodiments, the disclosure provides a composition comprising a Compound of the Disclosure and one or more carriers. The term "carrier" as used herein refers to a solid that can adsorb a liquid while retaining the general properties of a solid at room temperature. In some embodiments, the carrier is an inert material. In some embodiments, the carrier has a high surface area. In some embodiments, the carrier comprises particles with diameters of less than 500 microns.

[0151] In some embodiments, the composition comprises from about 15 wt / wt % to about 85 wt / wt % of one or more carriers. In some embodiments, the composition comprises from about 1 wt / wt % to about 5 wt / wt %, from about 1 wt / wt % to about 15 wt / wt %, from about 1 wt / wt % to about 25 wt / wt %, from about 1 wt / wt % to about 35 wt / wt %, from about 1 wt / wt % to about 45 wt / wt %, from about 1 wt / wt % to about 55 wt / wt %, from about 1 wt / wt % to about 65 wt / wt %, from about 1 wt / wt % to about 75 wt / wt %, from about 1 wt / wt % to about 85 wt / wt %, from about 1 wt / wt % to about 95 wt / wt %, from about 5 wt / wt % to about 15 wt / wt %, from about 5 wt / wt % to about 25 wt / wt %, from about 5 wt / wt % to about 35 wt / wt %, from about 5 wt / wt % to about 45 wt / wt %, from about 5 wt / wt % to about 55 wt / wt %, from about 5 wt / wt % to about 65 wt / wt %, from about 5 wt / wt % to about 75 wt / wt %, from about 5 wt / wt % to about 85 wt / wt %, from about 5 wt / wt % to about 95 wt / wt %, from about 15 wt / wt % to about 25 wt / wt %, from about 15 wt / wt % to about 35 wt / wt %, from about 15 wt / wt % to about 45 wt / wt %, from about 15 wt / wt % to about 55 wt / wt %, from about 15 wt / wt % to about 65 wt / wt %, from about 15 wt / wt % to about 75 wt / wt %, from about 15 wt / wt % to about 95 wt / wt %, from about 25 wt / wt % to about 35 wt / wt %, from about 25 wt / wt % to about 45 wt / wt %, from about 25 wt / wt % to about 55 wt / wt %, from about 25 wt / wt % to about 65 wt / wt %, from about 25 wt / wt % to about 75 wt / wt %, from about 25 wt / wt % to about 85 wt / wt %, from about 25 wt / wt % to about 95 wt / wt %, from about 35 wt / wt % to about 45 wt / wt %, from about 35 wt / wt % to about 55 wt / wt %, from about 35 wt / wt % to about 65 wt / wt %, fromabout 35 wt / wt % to about 75 wt / wt %, from about 35 wt / wt % to about 85 wt / wt %, from about 35 wt / wt % to about 95 wt / wt %, from about 45 wt / wt % to about 55 wt / wt %, from about 45 wt / wt % to about 65 wt / wt %, from about 45 wt / wt % to about 75 wt / wt %, from about 45 wt / wt % to about 85 wt / wt %, from about 45 wt / wt % to about 95 wt / wt %, from about 55 wt / wt % to about 65 wt / wt %, from about 55 wt / wt % to about 75 wt / wt %, from about 55 wt / wt % to about 85 wt / wt %, from about 55 wt / wt % to about 95 wt / wt %, from about 65 wt / wt % to about 75 wt / wt %, from about 65 wt / wt % to about 85 wt / wt %, from about 65 wt / wt % to about 95 wt / wt %, from about 75 wt / wt % to about 85 wt / wt %, from about 75 wt / wt % to about 95 wt / wt %, or from about 85 wt / wt % to about 95 wt / wt % of one or more carriers.

[0152] In some embodiments, the composition comprises about 15 wt / wt % of one or more carriers. In some embodiments, the composition comprises about 1 wt / wt %, about 5 wt / wt %, about 10 wt / wt %, about 20 wt / wt %, about 25 wt / wt %, about 30 wt / wt %, about 35 wt / wt %, about 40 wt / wt %, about 45 wt / wt %, about 50 wt / wt %, about 55 wt / wt %, about 60 wt / wt %, about 65 wt / wt %, about 70 wt / wt %, about 75 wt / wt %, about 80 wt / wt %, about 85 wt / wt %, about 90 wt / wt %, or about 95 wt / wt % of one or more carriers.

[0153] The present disclosure also provides processes for preparing a composition comprising a Compound of the Disclosure and one or more carriers, the process comprising admixing the compound and the one or more carriers.

[0154] The present disclosure also provides lubricant compositions comprising a Compound of the Disclosure and a lubricant. Non-limiting examples of lubricants include mineral oil, higher molecular weight petroleum distillates such as aromatic, naphthenic, and paraffinic distillates, synthetic oils such as polyalpha-olefin (PAO), synthetic esters, polyalkylene glycols (PAG), phosphate esters, perfluoropolyether (PFPE), alkylated naphthlalenes (AN), silicate esters, ionic fluids, and multiply alkylated cyclopentanes (MAC), solid lubricants such as polytetrafluoroethylene (PTFE), graphite, hexagonal boron nitride, molybdenum disulfide, tungsten disulfide, aqueous lubricants such as hydrated brush polymers, and biolubricants such as triglyceride esters, high oleic canola oil, castor oil, palm oil, sunflower seed oil, and rapeseed oil.

[0155] The present disclosure also provides combustible fuel compositions comprising a combustible fuel and a Compound of the Disclosure. Non-limiting examples of combustible fuel include gasoline, diesel, kerosene, liquefied petroleum gas, synthetic fuel, and biodisesel.

[0156] The present disclosure also provides fuel additive compositions comprising a fuel additive and a Compound of the Disclosure. Non-limiting examples of fuel additives include oxygenates such as alcohols and ethers, antioxidants, stabilizers, detergents, antiknock agents, lead scavengers, fuel dyes, viscosity modifiers, and butyl rubber. In some embodiments, the butyl rubber is in the form of polyisobutylene succinimide. In some embodiments, the butyl rubber is added as a detergent to prevent fouling of diesel fuel injectors.

[0157] In some embodiments, the present disclosure provides a composition recited in Table 4.Table 4

[0158] In some embodiments, the vulcanized tire or other rubber article composition of Table 4 comprises about 0.1 wt / wt %, about 0.2 wt / wt %, about 0.3 wt / wt %, about 0.4wt / wt %, about 0.5 wt / wt %, about 0.6 wt / wt %, about 0.7 wt / wt %, about 0.8 wt / wt %, about 0.9 wt / wt %, about 1 wt / wt %, about 2 wt / wt %, about 3 wt / wt %, about 4 wt / wt %, about 5 wt / wt %, about 6 wt / wt %, about 7 wt / wt %, about 8 wt / wt %, about 9 wt / wt %, or about 10 wt / wt % of a Compound of the Disclosure. In some embodiments, the vulcanized tire or other rubber article of Table 4 comprises comprises about 5 wt / wt %, about 10 wt / wt %, about 15 wt / wt %, about 20 wt / wt %, about 25 wt / wt %, about 30 wt / wt %, about 35 wt / wt %, about 40 wt / wt %, about 45 wt / wt %, about 50 wt / wt %, about 55 wt / wt %, about 60 wt / wt %, about 65 wt / wt %, about 70 wt / wt %, about 75 wt / wt %, about 80 wt / wt %, about 85 wt / wt %, about 90 wt / wt %, or about 95 wt / wt % of at least one elastomer.

[0159] In some embodiments, the unvulcanized in-tire component or built up component or other end use component composition of Table 4 comprises about 0.01 wt / wt %, about 0.02 wt / wt %, about 0.03 wt / wt %, about 0.04 wt / wt %, about 0.05 wt / wt %, about 0.06 wt / wt %, about 0.07 wt / wt %, about 0.08 wt / wt %, about 0.09 wt / wt %, about 0.1 wt / wt %, about 0.2 wt / wt %, about 0.3 wt / wt %, about 0.4 wt / wt %, about 0.5 wt / wt %, about 0.6 wt / wt %, about 0.7 wt / wt %, about 0.8 wt / wt %, about 0.9 wt / wt %, about 1 wt / wt %, about 2 wt / wt %, about 3 wt / wt %, about 4 wt / wt %, about 5 wt / wt %, about 6 wt / wt %, about 7 wt / wt %, about 8 wt / wt %, about 9 wt / wt %, or about 10 wt / wt % of a Compound of the Disclosure. In some embodiments, the unvulcanized in-tire component or built up component or other end use component composition of Table 4 comprises comprises about 5 wt / wt %, about 10 wt / wt %, about 15 wt / wt %, about 20 wt / wt %, about 25 wt / wt %, about 30 wt / wt %, about 35 wt / wt %, about 40 wt / wt %, about 45 wt / wt %, about 50 wt / wt %, about 55 wt / wt %, about 60 wt / wt %, about 65 wt / wt %, about 70 wt / wt %, about 75 wt / wt %, about 80 wt / wt %, about 85 wt / wt %, about 90 wt / wt %, or about 95 wt / wt % of at least one elastomer.Vulcanized Elastomeric Articles

[0160] The present disclosure also provides vulcanized elastomeric articles comprising a Compound of the Disclosure. The term "vulcanized elastomeric article" refers to an article that is made by forming a composition comprising an elastomer into a specific shape and vulcanizing the composition to provide the article.

[0161] The present disclosure also provides vulcanized elastomeric articles prepared using a composition described herein.

[0162] In some embodiments, the vulcanized elastomeric article is a tire. In some embodiments, the tire is a passenger vehicle tire, a light truck tire, a heavy truck or bus tire, a motorcycle tire, an agriculture tire, an earthmover tire, an airplane tire, or a racing tire.

[0163] In some embodiments, the vulcanized elastomeric article is a component of a tire.In some embodiments, the component is a bead, a belt, a body ply, an inner liner, a sidewall, an undertread, or a tread.

[0164] In some embodiments, the vulcanized elastomeric article is a rubber overshoe, a sealing strip, an acoustic panel, an air spring, a bellow, a membrane, a tactile sensor, a crash pad, a hose, a conveyor belt, or a flooring.

[0165] In some embodiments, the vulcanized elastomeric article comprises about 0.1 phr to about 10 phr of the Compound of the Disclosure. For example, the vulcanized elastomeric article comprises about 0.1 phr, about 0.2 phr, about 0.3 phr, about 0.4 phr, about 0.5 phr, about 0.6 phr, about 0.7 phr, about 0.8 phr, about 0.9 phr, about 1 phr, about 2 phr, about 3 phr, about 4 phr, about 5 phr, about 6 phr, about 7 phr, about 8 phr, about 9 phr, or about 10 phr of the Compound of the Disclosure.

[0166] In some embodiments, the present disclosure provides a vulcanized elastomeric article, e.g., a tire, comprising the components in Table 5.Table 5Processes

[0167] The present disclosure also provides processes for preparing a vulcanized elastomeric article, the process comprising:(a) forming a composition described herein into a formed shape; and (b) vulcanizing the formed shape,to provide a vulcanized elastomeric article.

[0168] In some embodiments, the vulcanizing is performed at an average temperature of from about 140 °C to about 160 °C. In some embodiments, the vulcanizing is performed at an average temperature of from about 80 °C to about 100 °C, from about 80 °C to about 120 °C, from about 80 °C to about 140 °C, from about 80 °C to about 160 °C, from about 80 °C to about 180 °C, from about 80 °C to about 200 °C, from about 100 °C to about 120 °C, from about 100 °C to about 140 °C, from about 100 °C to about 160 °C, from about 100 °C to about 180 °C, from about 100 °C to about 200 °C, from about 120 °C to about 140 °C, from about 120 °C to about 160 °C, from about 120 °C to about 180 °C, from about 120 °C to about 200 °C, from about 140 °C to about 180 °C, from about 140 °C to about 200 °C, from about 160 °C to about 180 °C, from about 160 °C to about 200 °C, or from about 180 °C to about 200 °C.

[0169] In some embodiments, the vulcanizing is performed at an average temperature of about 150 °C. In some embodiments, the vulcanizing is performed at an average temperature of about 80 °C, about 100 °C, about 120 °C, about 140 °C, about 160 °C, about 180 °C, or about 200 °C.

[0170] The present disclosure also provides processes for retreading tires, the process comprising:(a) applying a composition described herein to a tire;(b) disposing a pre-vulcanized tread around the tire;(c) disposing a curing envelope around the tire; and(d) vulcanizing the tire.Kits

[0171] The present disclosure also provides kits comprising a composition described herein, packaged in a manner, e.g., in a container, that facilitates use of the composition to practice the processes and / or methods of the present disclosure. In some embodiments, the kit comprises a composition described herein and instructions for using the composition in a vulcanizable elastomeric composition. In some embodiments, the kit comprises a composition described herein and instructions for using the composition to prepare a vulcanized elastomeric article. The composition may be packaged in any suitable container, such as a sealed bottle or vessel, with a label affixed to the ceontainer or included in the kit that describes the composition and proper use thereof.EXAMPLESEXAMPLE 1Synthesis of N1-methyl-N1-(4-methylpentan-2-yl)-N4-phenylbenzene-l,4-diamine (Compound 1)

[0172] To a flame-dried 1 L round-bottom flask equipped with a stir bar was charged N1- (4-methylpentan-2-yl)-N4-phenylbenzene-l,4-diamine (50.000 g, 1 Eq, 186.29 mmol), potassium carbonate (77.235 g, 3 Eq, 558.87 mmol), and DMF (200 mL). The reaction was placed under active nitrogen and allowed to stir in an ice-bath for 20 minutes before equipping the flask with an addition funnel containing iodomethane (27.8 g, 12.2 mL, 1.05 Eq, 196 mmol) in 50 mL of DMF. The reaction was allowed to stir at 0 °C as the methyl iodide solution was added dropwise over the course of 30 minutes. Upon complete addition, the reaction was allowed to slowly warm to room temperature and stir for 16 hours. After this time, the reaction was diluted with 400 mL of EtOAc and transferred to a separatory funnel. The organic layer was washed with water (5x200mL) to remove DMF and then with brine (lOOmL) before drying the organic layer over sodium sulfate. The organic layer was concentrated by rotary evaporation to afford a viscous dark oil which was purified by flash column chromatography (2% EtOAc / 98% Hexanes, analyzed by TLC 10% EtOAc / 90% Hexanes Rf=0.6) to afford the title compound as a red, low-melting solid N1- methyl-N1-(4-methylpentan-2-yl)-N4-phenylbenzene-l,4-diamine (34.227 g, 121.19 mmol, 65.1 %). 'H NMR (80 MHz, DMSO-de) 6 7.56 (s, 1H), 7.35 - 6.05 (m, 9H), 3.86 (h, J = 6.5 Hz, 1H), 2.55 (s, 3H), 1.92 - 0.09 (m, 12H).13C NMR (20 MHz, DMSO-de) 6 146.05, 145.63, 132.22, 128.86, 121.55, 117.28, 114.63, 51.13, 42.99, 29.75, 24.58, 22.87, 22.31, 16.48.EXAMPLE 2Synthesis of N1-methyl-N4-(4-methylpentan-2-yl)-N1-phenylbenzene-l,4-diamine (CompoundStep 1

[0173] To a flame-dried 1 liter roundbottom flask equipped with a stir bar was added Pd2(DBA)3 (3.49 g, 0.01 Eq, 3.81 mmol), sodium 2-methylpropan-2-olate (47.6 g, 1.3 Eq, 495 mmol), and dicyclohexyl(2',4',6'-triisopropyl-[l,r-biphenyl]-2-yl)phosphane (3.63 g, 0.02 Eq, 7.62 mmol). The atmosphere was exchanged with nitrogen through 3x vacuum refill cycles. Toluene (600 mL) was added and the mixture was allowed to stir for 15 minutes. Then, l-chloro-4-nitrobenzene (60.0 g, 1 Eq, 381 mmol) was added as a solution in 100 mL of toluene. The resulting mixture was allowed to stir at room temperature for 30 minutes before N-methylaniline (41.2 g, 41.7 mL, 1.01 Eq, 385 mmol) was added in one portion. The reaction was equipped with a reflux condenser and the atmosphere was again exchanged with nitrogen and allowed to stir at reflux for 2 hours. The reaction was diluted with 200 mL of EtOAc, filtered over a pad of celite, and transferred to a separatory funnel. The organic layer was washed with water (2x200mL), brine (1x100 mL), dried over sodium sulfate, and filtered over a 4 inch pad of silica gel washing with EtOAc. The solvent was removed by rotary evaporation to afford a dark orange-brown liquid. This material was used without any further purification, N-methyl-4- nitro-N-phenylaniline (78.457 g, 343.73 mmol, 90.3% yield).Step 2

[0174] To a stainless steel autoclave was charged N-methyl-4-nitro-N-phenylaniline (10.0 g, 1 Eq, 43.8 mmol), phosphoric acid (1 drop), IPA (100 mL), 4-methylpentan-2-one (25.7 g, 32.0 mL, 5.85 Eq, 256 mmol), and 597 mg of 3% Pt / C sulfided from Johnson Matthey. The autoclave was assembled, atmosphere was exchanged with nitrogen, and the mixture was allowed to stir at 1500 RPM before heating the mixture to 230 °C. The reaction was then continuously fed with 650 PSI of Eb and allowed to stir at this temperature and pressure for 4 hours. The reaction was cooled to room temperature and the contents of the autoclave were removed by filtration to afford a bright yellow liquid that slowly changed color to orange. The reaction mixture was concentrated by rotary evaporation and purified by flash column chromatography, 5% EtOAc / 95% Hexanes to afford the desired product as a bright yellow oil that solidifies upon standing, N1-methyl-N4-(4-methylpentan-2-yl)- Nkphenylbenzene-fd-diamine (1.286 g, 4.553 mmol, 10.4% yield). *HNMR (80 MHz, DMSO-de) 67.62 - 6.22 (m, 9H), 5.24 (d, J = 8.4 Hz, 1H), 3.48 - 3.39 (m, 1H), 2.14 - 0.50 (m, 12H).13C NMR (20 MHz, DMSO-de) 6 149.96, 145.91, 136.51, 128.54, 127.05, 116.45, 113.54, 112.88, 45.94, 45.46, 40.14, 24.48, 22.63, 20.66.EXAMPLE 3Synthesis of N1,N4-dimethyl-N1-(4-methylpentan-2-yl)-N4-phenylbenzene-l,4-diamine (Compound 57)

[0175] To a flame-dried 1 L round-bottom flask equipped with a stir bar was charged N1- (4-methylpentan-2-yl)-N4-phenylbenzene-l,4-diamine (40.000 g, 1 Eq, 149.03 mmol), potassium carbonate (61.788 g, 3 Eq, 447.09 mmol) and DMF (200 mL). The reaction was placed under active nitrogen and allowed to stir in an ice-bath for 20 minutes before equipping the flask with an addition funnel containing iodomethane (59.230 g, 26.0 mL, 2.8 Eq, 417.29 mmol) in 50 mL of DMF. The reaction was allowed to stir at 0 °C as the methyl iodide solution was added dropwise over the course of 30 minutes. Upon complete addition, the reaction was allowed to slowly warm to room temperature and stir for 16 hours. After this time, the reaction was diluted with 400 mL of EtOAc and transferred to a separatory funnel. The organic layer was washed with water (5x200mL) to remove DMF and then with brine (lOOmL) before drying the organic layer over sodium sulfate. The organic layer was concentrated by rotary evaporation to afford a viscous dark blue oil which was purified by flash column chromatography (2% EtOAc / 98% Hexanes, analyzed by TLC 10% EtOAc / 90% Hexanes 5 spots Rf= 0.8) to afford the title compound as a light red oil that slowly crystallizes upon standing, N1,N4-dimethyl-N1-(4-methylpentan-2-yl)-N4- phenylbenzene-l,4-diamine (8.318 g, 28.06 mmol, 18.8 % yield). 'H NMR (80 MHz, DMSO-de) 6 7.52 - 6.29 (m, 9H), 4.23 - 3.68 (m, 1H), 3.12 (s, 3H), 2.59 (s, 3H), 1.93 - 0.32 (m, 12H).13C NMR (20 MHz, DMSO-de) 6 150.06, 147.74, 137.61, 128.89, 126.82, 114.39, 113.54, 50.71, 43.45, 42.03, 41.00, 40.35, 38.96, 29.89, 24.89, 23.13, 22.57, 16.97.EXAMPLE 4Synthesis of Nl,N4-dicyclohexyl-Nl-methylbenzene-L4-diamine (Compound 2) and N N4- di cyclohexyl-N',N4-dimethylbenzene-L4-di amine (Compound 60)Compound 2 Compound 60

[0176] To a 250 mL round-bottom flask equipped with a stir bar was added N N4- dicyclohexylbenzene-l,4-diamine (15.009 g, 1 Eq, 55.091 mmol), K2CO3 (11.420 g, 1.5 Eq, 82.637 mmol), and DMF (50.0 mL). The reaction mixture was allowed to stir under nitrogen while cooling to 0 °C. After stirring for 5 minutes, iodomethane (8.2 g, 3.6 mL, 1.0 Eq, 58 mmol) was added over the course of 10 minutes. Upon complete addition, the reaction mixture was allowed to stir for 16 hours at room temperature. The reaction was quenched with 10 ml of water and transferred to a separatory funnel. The organic layer was diluted with diethyl ether (100 mL), and washed with water (4x100 mL), brine (50 mL), and dried over sodium sulfate. The organic layer was collected and concentrated by rotary evaporation and the resulting dark purple oil was purified by flash column chromatography (10% EtOAc / 90% hexanes) to afford Nl,N4-dicyclohexyl-Nl,N4-dimethylbenzene-l,4- diamine (1.026 g, 3.414 mmol, 6.2 %) ( Rf= 0.3 in 10% EtOAc / Hexanes) as a light pink, microcrystalline solid. Further elution afforded Nl,N4-dicyclohexyl-Nl-methylbenzene- 1,4-diamine (1.622 g, 5.662 mmol, 10.3 % yield) (Rf=0.2 in 10% EtoAc / Hexanes) as a dark purple solid.

[0177] Nl,N4-dicyclohexyl-Nl,N4-dimethylbenzene-l,4-diamine (Compound 2): 'H NMR (80 MHz, CD2CI2) 66.65 (q, J = 9.0 Hz, 4H), 3.30 (s, 2H), 3.17 (s, 1H), 2.69 (s, 3H), 2.36 -0.73 (m, 20H).13C NMR (20 MHz, CD2CI2) 6 143.46, 118.22, 61.0326.65, 26.61, 26.54, 25.59.

[0178] Nl,N4-dicyclohexyl-Nl-i'nethylbenzene-l,4-diamine (Compound 60): 'H NMR (80 MHz, CD2CI2) 66.80 (s, 4H), 3.79 - 3.07 (m, 2H), 2.72 (s, 6H), 2.20 - 0.79 (m, 20H).13C NMR (20 MHz, CD2CI2) 6 143.65, 117.07, 60.52, 32.78, 30.30, 26.68, 26.55.EXAMPLE 5Synthesis of Nl-methyl-Nl,N4-bis(5-methylhexan-2-yl)benzene-l,4-diamine (Compound 3)

[0179] To a stirred solution ofNl,N4-bis(5-methylhexan-2-yl)benzene-l,4-diamine (300.0 g, 0.986 mol, crude) in DMF (3.0 L, 10.0 vol) was added potassium carbonate (204.0 g, 1.48 mol) at RT. After stirring for 15-20 min at RT, the reaction was cooled to 0-5°C and methyl iodide (43.0 mL, 0.690 mol) was added dropwise over a period of 45-60 min. The resulting reaction mixture was warmed to RT and stirred for 4 h. After completion ofreaction (monitored by TLC), the reaction was quenched with chilled water, extracted with ethyl acetate (3.0 L) and dried over sodium sulfate. After filtration, evaporation of the solvent under reduced pressure at 40-45°C afforded 380.0 g of crude.

[0180] The crude compound was purified by silica-gel (100-200 mesh) column chromatography eluting with 2-4% ethyl acetate in hexane. Solvent was evaporated under vacuum to afford Nl-methyl-Nl,N4-bis(5-methylhexan-2-yl)benzene-l,4-diamine (36 % yield, >98 % pure by HPLC 260 nm, Mass (m / z): 319.34 [M+H]+), as a reddish-brown liquid. 'HNMR (400 MHz, Pyridine-t / j): 86.92 (d, J= 8.0 Hz, 2H), 6.84 (d, J= 8.4 Hz, 2H), 4.53 (s, 1H), 3.67-3.60 (m, 1H), 3.47-3.41 (m, 1H), 2.59 (s, 3H), 1.61-1.53 (m, 2H), 1.51- 1.22 (m, 8H), 1.18 (d, J= 6.4 Hz, 3H), 1.00 (d, J= 6.4 Hz, 3H), 0.83 (t, J= 6.4 Hz, 12H).13C NMR (100 MHZ, Pyridine-tZs): 6 143.89, 141.96, 118.20, 115.35, 56.88, 50.11, 37.00, 36.27, 35.77, 32.84, 31.34, 28.91, 28.81, 23.37, 23.29, 23.24, 23.23, 21.52, 16.75.EXAMPLE 6Synthesis of Synthesis of Nl,N4-dicyclohexyl-Nl,N4-diisopropylbenzene-l,4-diamine (Compound 53)

[0181] To a stirred solution of Nl,N4-dicyclohexylbenzene-l,4-diamine (90.0 g, 0.330 mol) in DMF (450.0 mL, 5.0 vol) was added potassium carbonate (182.4 g, 1.32 mol) at RT. After stirring for 25-30 min at RT, isopropyl iodide (99.0 mL, 0.991 mol) was added dropwise over 45-60 min and the resulting reaction mixture was stirred at RT for 3 days. After completion of reaction (monitored by TLC), the reaction was cooled to RT, quenched with chilled water and extracted with ethyl acetate (1.0 L). The organic layer was separated and washed with a brine solution (500 mL). After separation, the organic layer was dried over sodium sulfate, filtered and solvent was removed under reduced pressure at 40-45°C to afford a crude.

[0182] The crude compound was purified by silica-gel (100-200 mesh) column chromatography eluting with 1-3% ethyl acetate in hexane. Solvent was removed under vacuum to afford 50.0 g of Nl,N4-dicyclohexyl-Nl,N4-diisopropylbenzene-l,4-diamine (43% yield, >98 % pure by HPLC 260 nm, Mass (m / z): 357.24 [M+H]+), as a pale-yellowsolid. 'HNMR (400 MHz, pyridine-t / j): 6 7.03 (s, 4H), 3.65-3.58 (m, 2H), 3.22-3.17 (m, 2H), 1.82-1.79 (m, 4H), 1.70-1.67 (m, 4H), 1.52-1.49 (m, 2H), 1.43-1.33 (m, 4H), 1.29- 1.19 (m, 4H), 1.13 (d, J= 6.8 Hz, 12H), 1.09-0.99 (m, 2H).13C NMR (100 MHz, pyridine- d5. 5 142.29, 58.21, 48.49, 32.63, 26.82, 26.64, 22.25.EXAMPLE 7Synthesis of Nl,N4-dicyclohexyl-Nl,N4-dimethylbenzene-l,4-diamine (Compound 60)

[0183] To a stirred solution of Nl,N4-dicyclohexylbenzene-l,4-diamine (110.0 g, 0.404 mol) in DMF (550.0 mL, 5.0 vol) was added potassium carbonate (198.0 g, 1.413 mol) at RT. After stirring for 15-20 min at RT, the reaction was cooled to 0-5°C and methyl iodide (37.7 mL, 0.606 mol) was added dropwise over a period of 45-60 min. The resulting reaction mixture was warmed to RT and stirred for 24 h. After 24 h, the reaction was cooled to 0-5°C and methyl iodide (12.5 mL, 0.202 mol) was added. The reaction was warmed to RT and stirred for another 24 h. After completion of reaction (monitored by TLC), the reaction was quenched with chilled water and the obtained solid was filtered and extracted with ethyl acetate (1.0 L). The separated organic layer was washed with brine (500 mL), dried over sodium sulfate, filtered and solvent was evaporated under reduced pressure at 40-45°C to afford 134 g of crude compound. The crude was purified by silica-gel (100- 200 mesh) column chromatography eluting with 3-5% ethyl acetate in hexane. Solvent was evaporated under vacuum to afford 40.0 g of N l,N4-di cyclohexyl -N1,N4- dimethylbenzene-l,4-diamine (33 % yield, >99 % pure by HPLC 260 nm, Mass (m / z): 301.24 [M+H]+) as a pink solid.XH NMR (400 MHz, TFA-t / ): 87.58 (s, 4H), 3.45-3.40 (m, 2H), 3.15 (s, 6H), 2.14-2.11 (m, 2H), 1.78-1.74 (m, 2H), 1.63-1.60 (m, 2H), 1.51-1.45 (m, 4H), 1.31-0.88 (m, 10H).13C NMR (100 MHz, TFA-t / ): 6 143.72, 127.04, 73.80, 44.24, 31.19, 30.53, 26.41, 26.03.EXAMPLE 8Synthesis of N1 ,N4-diethyl-N 1 ,N4-bis(4-methylpentan-2-yl)benzene- 1 ,4-diamine (Compound 39)

[0184] To a stirred solution of Nl,N4-bis(4-methylpentan-2-yl)benzene-l,4-diamine (100.0 g, 0.362 mol) in DMF (500.0 L, 5.0 vol) was added potassium carbonate (150.0 g, 1.08 mol) at RT. After stirring for 15-20 min at RT, ethyl iodide (56.0 mL, 0.724 mol) was added dropwise for a period of 45-60 min and stirred at RT for 32 h. After completion of reaction (monitored by TLC), the reaction was quenched with chilled water, extracted with ethyl acetate (1.0 L), washed with brine (1.0 L) and the separated the organic layer was dried over sodium sulfate. After filtration solvent was evaporated under reduced pressure at 40-45°C to afford 140.0 g of crude compound. The crude was purified by silica-gel (100- 200 mesh) column chromatography eluting in only hexane. Solvent was evaporated under vacuum to affordNl,N4-diethyl-Nl,N4-bis(4-methylpentan-2-yl)benzene-l,4-diamine (75 % yield, >96 % pure by HPLC 260 nm, Mass (m / z): 333.35 [M+H]+) as a reddish-brown liquid. 'H NMR (400 MHz, Acetone-tfc): 6 6.76 (s, 4H), 3.70 (s, 2H), 3.11 (s, 4H), 1.77- 1.67 (m, 2H), 1.58-1.51 (m, 2H), 1.23-1.16 (m, 2H), 1.06-1.02 (m, 12H), 0.92-0.90 (m, 12H).13C NMR (100 MHz, Acetone-tfc): 6142.05, 54.45, 44.96, 38.69, 30.49, 30.30, 30.10, 29.91, 29.72, 29.53, 29.33, 25.78, 23.39, 23.22, 17.72, 15.13.EXAMPLE 9Synthesis of Nl, N4-di ethyl -Nl, N4-bis(5-methylhexan-2-yl) benzene- 1,4-diamine (Compound 63)

[0185] To a stirred solution ofNl,N4-bis(5-methylhexan-2-yl)benzene-l,4-diamine (100.0 g, 0.329 mol) in DMF (1.0 L, 10.0 vol) was added potassium carbonate (90.7 g, 0.658 mol) at RT. After stirring for 15-20 min at RT, ethyl iodide (52.7 mL, 0.658 mol) was addeddropwise for 45-60 min. The resulting reaction mixture was stirred at RT for 16 h. After completion of reaction (monitored by TLC), the reaction was quenched with chilled water and extracted with ethyl acetate (1.0 L). The separated organic layer was dried over sodium sulfate, filtered and solvent was evaporated under reduced pressure at 40-45°C to afford 130.0 g of crude. The crude was purified by silica-gel (100-200 mesh) column chromatography eluting with 1-3% ethyl acetate in hexane. The collected fractions were evaporated under vacuum to afford Nl, N4-di ethyl -Nl, N4-bis(5-methylhexan-2-yl) benzene- 1,4-diamine (80 % yield, >98 % pure by HPLC 260 nm, Mass (m / z): 361.20 [M+H]+), as a reddish-brown liquid. 'H NMR. (400 MHz, Pyridine-tZs): 86.98 (s, 4H), 3.62 (q, J= 6.8 Hz, 2H), 3.12 (q, J= 6.8 Hz, 4H), 1.63-1.56 (m, 2H), 1.51-1.44 (m, 2H), 1.43- 1.29 (m, 4H), 1.27-1.18 (m, 2H), 1.11 (t, J= 6.8 Hz, 6H), 1.05 (d, J= 6.4 Hz, 6H), 0.85 (d, J= 6.8 Hz, 12H).13C NMR (100 MHz, Pyridine-^): 6 142.10, 118.51, 56.83, 38.79, 36.99, 33.33, 28.81, 23.22, 23.19, 18.01, 15.27.EXAMPLE 10Synthesis of N-(4-methylpentan-2-yl)-N-(4-((4-methylpentan-2- yl)amino)phenyl)acetamide (Compound 30)

[0186] To a stirred solution of Nl,N4-bis(4-methylpentan-2-yl)benzene-l,4-diamine (450.0 g, 1.63 mol) in DCM (2.2 L, 5.0 vol) was added pyridine (788.0 mL, 9.78 mol) and DMAP (20.0 g, 0.163 mol), followed by the dropwise addition of acetyl chloride (174.0 mL, 2.44 mol) at 0-5°C over a period of 45-60 min. The resulting reaction mixture was allowed to stir at RT for 48 h. After completion of reaction (monitored by TLC), the reaction was quenched with water, the organic layer was separated and washed with brine solution (1.0 L). The separated organic layer was dried over sodium sulfate, filtered and solvent was evaporated under reduced pressure at 40-45°C to afford 790.0 g of crude. The crude was purified by silica-gel (100-200 mesh) column chromatography eluting with 4- 7% ethyl acetate in hexane. The collected fractions were evaporated under vacuum to afford 92.0 g of N-(4-methylpentan-2-yl)-N-(4-((4-methylpentan-2-yl)amino)phenyl)acetamide (24 % yield, >99 % pure by HPLC 260 nm, Mass (m / z): 319.36 [M+H]+), as a pale-pinksolid. 'HNMR (400 MHz, DMSO-tfc): 66.81-6.77 (m, 2H), 6.55 (d, J= 8.8 Hz, 2H), 5.58 (d, J= 8.0 Hz, 1H), 4.84-4.78 (m, 1H), 3.45-3.34 (m, 1H), 1.73-1.70 (m, 1H), 1.60 (s, 3H), 1.57-1.54 (m, 1H), 1.46-1.40 (m, 1H), 1.25-1.17 (m, 2H), 1.06 (dd, J= 6.0, 1.2 Hz, 3H), 0.98-0.95 (m, 1H), 0.93-0.85 (m, 15H).13C NMR (100 MHz, DMSO-tfc): 6 169.56, 147.76, 130.79, 130.19, 125.85, 111.86, 46.38, 45.83, 45.27, 43.55, 24.48, 23.08, 22.72, 22.68, 22.63, 22.53, 20.55, 19.44.EXAMPLE 11Synthesis of Nl,N4-dicy cl ohexyl-Nl,N4-di ethylbenzene- 1,4-diamine (Compound 64)

[0187] To a stirred solution of Nl,N4-di cyclohexylbenzene- 1,4-diamine (103.0 g, 0.378 mol) in DMF (515.0 mL, 5.0 vol) was added potassium carbonate (208.6 g, 1.512 mol) at RT. After stirring for 15-20 min at RT, the reaction was cooled to 0-5°C and ethyl iodide (91.1 mL, 1.13 mol) was added dropwise over a period of 45-60 min. The resulting reaction mass was warmed to RT and stirred for 16 h. After completion of reaction (monitored by TLC), the material was quenched with chilled water and extracted with ethyl acetate (1.0 L). The organic layer was separated and washed with brine solution (500.0 mL). The organic layer was dried over sodium sulfate, filtered and solvent was evaporated under reduced pressure at 40-45°C to afford 110.0 g of crude. The crude was purified by silica- gel (100-200 mesh) column chromatography eluting with 2-4% ethyl acetate in hexane. Solvent from the fractions was evaporated under vacuum to afford 85.0 g of N1,N4- dicyclohexyl-Nl,N4-di ethylbenzene- 1,4-diamine (68 % yield, >99 % pure by HPLC 260 nm, Mass (m / z): 329.5 [M+H]+) as a pale-pink solid. 'H NMR (400 MHz, TFA-t / ): 87.38 (s, 4H), 3.59-3.54 (m, 2H), 3.28-3.21 (m, 4H), 1.96 (br s, 2H), 1.54 (brd, J= 10.0 Hz, 2H), 1.41 (br d, J= 11.2 Hz, 2H), 1.28-1.23 (m, 4H), 1.04-0.77 (m, 8H), 0.69-0.66 (m, 8H).13C NMR (100 MHz, TFA- ): 6 140.70, 128.41, 73.27, 53.56, 31.59, 31.41, 26.81, 26.47, 12.04.EXAMPLE 12Synthesis of N1 ,N4-dimethyl-N 1 -(5-methylhexan-2-yl)-N4-phenylbenzene- 1 ,4-diamine (Compound 34)

[0188] To a stirred solution of Nl-(5-methylhexan-2-yl)-N4-phenylbenzene-l,4-diamine) (130.0 g, 0.460 mol in DMF (1.3 L, 10.0 vol) was added NaH (60% in oil) (37.8 g, 0.920 mol) at 0-5°C. After stirring for 30-40 min at 0-5°C, methyl iodide (163.6 g, 1.15 mol) was added dropwise over a period of 45-60 min. The resulting reaction mixture was warmed to RT and stirred atRT for 16 h. After completion of reaction (monitored by TLC), the mixture was quenched with chilled water and extracted with ethyl acetate (1.5 L). The organic layer was separated, dried over sodium sulfate, filtered and solvent was evaporated under vacuum to afford 180.0 g of crude. The crude was purified by silica-gel (100-200 mesh) column chromatography eluting with 1-3% ethyl acetate in hexane. Solvent was evaporated under vacuum to afford 20.0 g of Nl,N4-dimethyl-Nl-(5-methylhexan-2-yl)-N4- phenylbenzene-l,4-diamine (15% yield, >98 % pure by HPLC 260 nm, Mass (m / z): 311.25 [M+H]+) as an off-white solid. 'H NMR (400 MHz, DMSO-tfc): 67.11 (t, J= 7.6 Hz, 2H), 6.97 (d, J= 8.8 Hz, 2H), 6.77 (d, J= 8.8 Hz, 2H), 6.66-6.63 (m, 3H), 3.87-3.81 (m, 1H), 3.15 (s, 3H), 2.67 (s, 3H), 1.58-1.38 (m, 3H), 1.16-1.10 (m, 2H), 1.05 (d, J= 6.4 Hz, 3H), 0.85 (t, J= 6.4 Hz, 6H).13C NMR (100 MHz, CDCh): 6 149.78, 147.66, 137.20, 128.66, 126.61, 116.88, 114.01, 113.58, 53.02, 35.63, 31.70, 29.56, 27.50, 22.66, 22.44, 16.93.EXAMPLE 13Synthesis of Nl-methyl-Nl,N4-bis(5-methylhexan-2-yl)benzene-l,4-diamine (Compound13)

[0189] To a stirred solution ofNl,N4-bis(5-methylhexan-2-yl)benzene-l,4-diamine (200.0 g, 0.657 mol) in DMF (2.0 L, 10.0 vol) was added potassium carbonate (181.5 g, 1.31 mol) at RT. After stirring for 15-20 min at RT, the reaction was cooled to 0-5°C and ethyl iodide(123.0 g, 0.789 mol) was added dropwise over a period of 45-60 min. The resulting reaction mixture was allowed to stir at RT for 4 h. After completion of reaction (monitored by TLC), the reaction was quenched with chilled water and extracted with ethyl acetate (2.0 L). The organic layer was separated, dried over sodium sulfate, filtered and solvent was evaporated under reduced pressure at 40-45°C to afford 305.0 g of crude. The crude was purified by silica-gel (100-200 mesh) column chromatography eluting with 1-3% ethyl acetate in hexane. Solvent was evaporated under vacuum to afford N1 -methyl -Nl,N4-bis(5- methylhexan-2-yl)benzene-l,4-diamine (29 % yield, >98 % pure by HPLC 260 nm, Mass (m / z): 333.59 [M+H]+), as a reddish-brown liquid. 'H NMR. (400 MHz, DMSO-t / e): 86.62 (d, J= 8.8 Hz, 2H), 6.44 (d, J= 8.8 Hz, 2H), 4.63 (d, J= 8.4 Hz, 1H), 3.31-3.29 (m, 1H), 3.23-3.19 (m, 1H), 2.97 (q, J= 6.8 Hz, 2H), 1.52-1.45 (m, 4H), 1.33-1.14 (m, 6H), 1.04 (d, J= 6.0 Hz, 3H), 0.96-0.92 (m, 6H), 0.87-0.83 (m, 12H).13C NMR (100 MHz, DMSO-tfc): 8 141.28, 139.02, 119.33, 113.42, 56.48, 48.29, 38.23, 35.82, 35.05, 34.24, 32.03, 27.66, 27.61, 22.62, 22.56, 22.52, 20.55, 16.98, 14.38.EXAMPLE 14Synthesis of Nl-isopropyl-Nl,N4-bis(5-methylhexan-2-yl)benzene-l,4-diamine (Compound 28)

[0190] To a stirred solution ofNl,N4-bis(5-methylhexan-2-yl)benzene-l,4-diamine (200.0 g, 0.657 mol) in DMF (2.0 L, 10.0 vol) was added potassium carbonate (181.5 g, 1.31 mol) at RT. After stirring for 15-20 min at RT, the reaction was cooled to 0-5°C and isopropyl iodide (85.0 mL, 0.851 mol) was added dropwise for over a period of 45-60 min. The resulting reaction mixture was allowed to stir at RT for 40 h. After completion of reaction (monitored by TLC), the reaction was quenched with chilled water and extracted with ethyl acetate (2.0 L). The organic layer was separated, dried over sodium sulfate, filtered and solvent was evaporated under reduced pressure at 40-45°C to afford 280.0 g of crude. The crude was purified by silica-gel (100-200 mesh) column chromatography eluting with 3- 5% ethyl acetate in hexane. Solvent was evaporated to afford Nl-isopropyl-Nl,N4-bis(5- methylhexan-2-yl)benzene-l,4-diamine (35 % yield, >99 % pure by HPLC 260 nm, Mass(m / z): 347.44 [M+H]+) as a reddish-brown liquid.1H NMR (400 MHz, DMSO-t / e): 66.74 (d, J= 8.4 Hz, 2H), 6.41 (d, J= 8.4 Hz, 2H), 4.95 (d, J= 8.8 Hz, 1H), 3.41-3.38 (m, 1H), 3.27-3.23 (m, 1H), 3.17-3.12 (m, 1H), 1.50-1.43 (m, 2H), 1.41-1.31 (m, 3H), 1.29-1.05 (m, 5H), 1.05 (d, J= 6.4 Hz, 3H), 0.95-0.90 (m, 9H), 0.86-0.79 (m, 12H).13C NMR (100 MHz, DMSO-tL): 6 144.47, 135.26, 128.27, 111.99, 53.10, 48.28, 47.94, 35.38, 35.01, 34.16, 32.92, 27.73, 27.66, 22.66, 22.64, 22.57, 22.51, 21.43, 20.48, 18.40.EXAMPLE 15Synthesis of Nl,N4-dimethyl-Nl,N4-bis(5-methylhexan-2-yl)benzene-l,4-diamine (Compound 58)

[0191] To a stirred solution ofNl,N4-bis(5-methylhexan-2-yl)benzene-l,4-diamine (200.0 g, 0.657 mol) in DMF (2.0 L, 10.0 vol) was added potassium carbonate (272.3 g, 1.97 mol) at RT. After stirring for 15-20 min at RT, the reaction was cooled to 0-5°C and methyl iodide (186.8 g, 1.31 mol) was added dropwise for 45-60 min. The resulting reaction mixture was warmed to RT and stirred for 2 h. After completion of reaction (monitored by TLC), the reaction was quenched with chilled water and extracted with ethyl acetate (2.0 L). The organic layer was dried over sodium sulfate, filtered and solvent was evaporated under reduced pressure at 40-45°C to afford 250.0 g of crude. The crude was purified by silica-gel (100-200 mesh) column chromatography eluting with 1-3% ethyl acetate in hexane. Solvent was evaporated under vacuum to afford 49.0 g Nl,N4-dimethyl-Nl,N4- bis(5-methylhexan-2-yl)benzene-l,4-diamine (22 % yield, >96 % pure by HPLC 260 nm, Mass (m / z): 333.38 [M+H]+) as a pale-red liquid. 'H NMR (400 MHz, CDCh): 6 6.76 (s, 4H), 3.62 (s, 2H), 2.62 (s, 6H), 1.59-1.47 (m, 4H), 1.42-1.32 (m, 2H), 1.27-1.13 (m, 4H), 1.02 (d, J= 6.4 Hz, 6H), 0.87 (d, J= 2.8 Hz, 6H), 0.86 (d, J= 2.8 Hz, 6H).13C NMR (100 MHz, CDCh): 6 143.11, 116.01, 55.58, 36.24, 32.13, 30.49, 28.13, 22.71, 22.64, 16.30.EXAMPLE 16Synthesis of Nl,N4-dicyclohexyl-Nl -isopropylbenzene- 1,4-diamine (Compound 70)

[0192] To a stirred solution of Nl,N4-di cyclohexylbenzene- 1,4-diamine (150.0 g, 0.551 mol) in DMF (750.0 mL, 5.0 vol) was added potassium carbonate (113.0 g, 0.827 mol) at RT. After stirring for 15-20 min at RT, the reaction was cooled to 0-5°C and isopropyl iodide (64.6 mL, 0.661 mol) was added dropwise over a period of 45-60 min. The resulting reaction contents were allowed to warm to RT and stir for 24 h. After completion of reaction (monitored by TLC), the reaction was quenched with chilled water and extracted with ethyl acetate (1.0 L). The organic layer was washed with brine solution (500.0 mL), dried over sodium sulfate, filtered and solvent was evaporated under reduced pressure at 40-45°C to afford a crude. The crude was purified by silica-gel (100-200 mesh) column chromatography eluting with 1-3% ethyl acetate in hexane. Solvent was evaporated under vacuum to afford 66.0 g of Nl,N4-dicy cl ohexyl-Nl -isopropylbenzene- 1,4-diamine (38 % yield, >99 % pure by HPLC 260 nm, Mass (m / z): 315.31 [M+H]+) as a reddish-brown liquid. 'H NMR (400 MHz, DMSO-tfc): 66.76 (d, J= 8.8 Hz, 2H), 6.42 (d, J= 8.8 Hz, 2H), 5.09 (d, J= 8.0 Hz, 1H), 3.44-3.39 (m, 1H), 3.09-3.02 (m, 1H), 2.95-2.49 (m, 1H), 1.91- 1.88 (m, 2H), 1.72-1.47 (m, 8H), 1.32-1.29 (m, 2H), 1.26-1.17 (m, 5H), 1.14-1.02 (m, 3H), 0.89 (d, J= 6.4 Hz, 6H).13C NMR (100 MHz, DMSO-tfc): 6 144.65, 134.84, 129.30, 111.74, 56.72, 50.91, 47.35, 32.83, 31.34, 25.88, 25.65, 25.01, 24.65, 21.35.EXAMPLE 17Synthesis of N-cyclohexyl-N-(4-(cyclohexylamino)phenyl)acetamide (Compound 25)

[0193] To a stirred solution of Nl,N4-di cyclohexylbenzene- 1,4-diamine (100.0 g, 0.367 mol) in DCM (1.0 L, 10.0 vol) was added triethyl amine (205.9 mL, 1.47 mol) at 0-5°C. After stirring for 10-15 min at 0-5°C acetic anhydride (41.6 mL, 0.440 mol) was addeddropwise over 45-60 min. The resulting reaction mixture was allowed to stir at RT for 16 h. After completion of reaction (monitored by TLC), the reaction was quenched with water. The separated organic layer was washed with brine solution (500.0 mL) and the collected organic layer was dried over sodium sulfate, filtered and solvent was evaporated under reduced pressure at 40-45°C to afford a crude. The crude was purified by silica-gel (100- 200 mesh) column chromatography eluting with 35-40% ethyl acetate in hexane. Solvent was evaporated under vacuum to afford 92.0 g of N-cyclohexyl-N-(4- (cyclohexylamino)phenyl)acetamide (78 % yield, >97 % pure by HPLC 260 nm, Mass (m / z): 315.31 [M+H]+) as a pale-pink solid. 'H NMR (400 MHz, DMSO-tfc): 66.80 (d, J= 8.8 Hz, 2H), 6.54 (d, J= 8.8 Hz, 2H), 5.63 (d, J= 8.0 Hz, 1H), 4.37-4.29 (m, 1H), 3.18-3.11 (m, 1H), 1.92-1.89 (m, 2H), 1.73-1.65 (m, 7H), 1.59 (s, 3H), 1.52-1.49 (m, 1H), 1.37-1.09 (m, 7H), 0.99-0.81 (m, 3H).13C NMR (100 MHz, CDCh): 6 170.96, 146.92, 130.85, 128.59, 112.72, 53.54, 51.80, 33.43, 31.51, 25.85, 25.75, 25.42, 25.02, 23.48.EXAMPLE 18Synthesis of Nl-isopropyl-Nl-(4-methylpentan-2-yl)-N4-phenylbenzene-l,4-diamine (Compound 27)

[0194] To a stirred solution of Nl-(4-methylpentan-2-yl)-N4-phenylbenzene-l,4-diamine (100.0 g, 0.373 mol) in DMF (500.0 mL, 5.0 vol) was added potassium carbonate (257.0 g, 1.86 mol) at RT. After stirring for 15-20 min at RT, the reaction was cooled to 0-5°C and then 2-iodo propane (186.0 mL, 1.86 mol) was added dropwise over a period of 45-60 min. The resulting reaction contents were heated to 85-90°C and stirred for 72 h. After -70% completion of reaction (monitored by TLC), the reaction was cooled to RT, quenched with chilled water and extracted with ethyl acetate (1.0 L). The organic layer was separated and washed with brine solution (500.0 mL). The organic layer was dried over sodium sulfate, filtered and solvent was evaporated under reduced pressure at 40-45°C to afford 160.0 g of crude. The crude was purified by silica-gel (100-200 mesh) column chromatography eluting with 2-4% ethyl acetate in hexane. Solvent was evaporated under vacuum to afford 40.0 g of N1 -isopropyl -Nl-(4-methylpentan-2-yl)-N4-phenylbenzene-l,4-diamine (35 %yield, >98 % pure by HPLC 260 nm, Mass (m / z): 311.30 [M+H]+) as a brown liquid. 'H NMR (400 MHz, DMSO ): 67.80 (s, 1H), 7.14 (t, J= 8.0 Hz, 2H), 6.95 (dd, J= 8.4, 7.2 Hz, 4H), 6.83 (d, J= 8.8 Hz, 2H), 6.69 (t, J= 7.2 Hz, 1H), 3.59-3.53 (m, 1H), 3.48-3.38 (m, 1H), 1.70-1.62 (m, 1H), 1.40-1.33 (m, 1H), 1.20-1.14 (m, 1H), 1.09-1.04 (m, 6H), 0.87- 0.82 (m, 6H).13C NMR (100 MHz, DMSO-tfc): 6 145.01, 141.36, 135.79, 128.98, 123.26, 118.96, 118.08, 114.94, 50.34, 47.67, 44.70, 24.77, 23.18, 22.66, 22.41, 21.44, 18.49.EXAMPLE 19Synthesis of Nl-cyclohexyl-Nl-methyl-N4-phenylbenzene-l,4-diamine (Compound 8)

[0195] To a stirred solution of Nl-cyclohexyl-N4-phenylbenzene-l,4-diamine (80.0 g, 0.300 mol) inDMF (400.0 mL, 5.0 vol) was added potassium carbonate (62.2 g, 0.451 mol) at RT. After stirring for 15-20 min at RT, the reaction was cooled to 0-5°C and methyl iodide (18.7 mL, 0.300 mol) was added dropwise over a period of 45-60 min. The resulting reaction contents were allowed to stir at RT for 48 h. After completion of reaction (monitored by TLC), the reaction was quenched with chilled water and extracted with ethyl acetate (800.0 mL). The organic layer was washed with a brine solution (500.0 mL), dried over sodium sufate, filtered and solvent was evaporated under reduced pressure at 40-45°C to afford 52.0 g of crude. The crude was triturated with n-pentane to afford 42.0 g of Nicy cl ohexyl-Nl-methyl-N4-phenylbenzene-l,4-diamine (50 % yield, >98 % pure by HPLC 260 nm, Mass (m / z): 281.27 [M+H]+) as an off-white solid. 'H NMR (400 MHz, DMSO- d6y. 67.62 (s, 1H), 7.11 (t, J= 6.8 Hz, 2H), 6.97 (d, J= 8.8 Hz, 2H), 6.85 (d, J= 7.6 Hz, 2H), 6.75 (d, J= 8.8 Hz, 2H), 6.64 (t, J= 7.2 Hz, 1H), 3.49-3.44 (m, 1H), 2.67 (s, 3H), 1.78-1.75 (m, 2H), 1.68-1.60 (m, 3H), 1.47-1.29 (m, 4H), 1.15-1.09 (m, 1H).13C NMR (100 MHz, DMSO-tL): 6 146.04, 145.29, 132.42, 128.92, 121.45, 117.34, 114.62, 114.00, 58.04, 31.08, 29.33, 25.60, 25.47.EXAMPLE 20Synthesis of N1 -methyl -Nl-(5-methylhexan-2-yl)-N4-phenylbenzene-l,4-diamine (Compound 5)

[0196] To a stirred solution of Nl-(5-methylhexan-2-yl)-N4-phenylbenzene-l,4-diamine (240.0 g, 0.851 mol) in DMF (1.2 L, 5.0 vol) was added potassium carbonate (352.0 g, 2.55 mol) at RT. After stirring for 15-20 min at RT, the reaction was cooled to 0-5°C and methyl iodide (241.7 g, 1.70 mol) was added dropwise over a period of 45-60 min. The resulting reaction mixture was warmed to RT and stirred at RT for 16 h. After completion of reaction (monitored by TLC), the reaction was quenched with chilled water and extracted with ethyl acetate (1.5 L). Solid started to precipitate out in the organic layer. The solid was filtered and dried under vacuum to afford 105.0 g of a green solid. The solid from two batches (200.0 g) was dissolved in DMF (2.0 L, 10.0 vol) and to this was added triphenyl phosphine (168.6 g, 0.643 mol) atRT. The mixture was heated to 100-105°C and stirred for 16 h. After completion of reaction (monitored by TLC), the reaction was cooled to RT, quenched with chilled water and extracted with ethyl acetate (2.0 L). The organic layer was dried over sodium sulfate and solvent was evaporated under vacuum to afford 180.0 g of crude. The crude was purified by silica-gel (100-200 mesh) column chromatography eluting with 2- 5% ethyl acetate in hexane. Solvent was evaporated under vacuum to afford Nl-methyl- Nl-(5-methylhexan-2-yl)-N4-phenylbenzene-l,4-diamine (48 % yield, >98 % pure by HPLC 260 nm, Mass (m / z): 297.24 [M+H]+) as a black liquid. 'HNMR (400 MHz, DMSO- d6y. 67.57 (s, 1H), 7.10 (dd, J= 8.4, 7.6 Hz, 2H), 6.95 (d, J= 8.8 Hz, 2H), 6.82 (d, J= 7.6 Hz, 2H), 6.73 (d, J= 8.8 Hz, 2H), 6.63 (t, J= 7.2 Hz, 1H), 3.79-3.71 (m, 1H), 2.59 (s, 3H), 1.56-1.47 (m, 2H), 1.46-1.36 (m, 1H), 1.17-1.13 (m, 2H), 1.01 (d, J= 6.4 Hz, 3H), 0.85 (d, J= 6.0 Hz, 3H).13C NMR (100 MHz, CDCh): 6 147.09, 145.83, 132.10, 128.95, 121.58, 117.30, 114.15, 113.94, 53.67, 35.69, 31.59, 29.72, 27.50, 22.67, 22.47, 16.67.EXAMPLE 21Synthesis of N1 -methyl-N 1 ,N4-bis(4-methylpentan-2-yl)benzene- 1 ,4-diamine (Compound 4)

[0197] To a stirred solution of Nl,N4-bis(4-methylpentan-2-yl)benzene-l,4-diamine (240.0 g, 0.868 mol) in DMF (1.2 L, 5.0 vol) was added potassium carbonate (180.0 g, 1.302 mol) at RT. After stirring for 15-20 min at RT, the reaction was cooled to 0-5°C and methyl iodide (54.0 mL, 0.868 mol) was added dropwise for 45-60 min. The resulting reaction contents were allowed to stir at RT for 16 h. After completion of reaction (monitored by TLC), the reaction was quenched with chilled water and extracted with ethyl acetate (1.5 L). The organic layer was washed with brine solution (1.0 L). The organic layer was dried over sodium sulfate, filtered and solvent was evaporated under reduced pressure at 40-45°C to afford 210.0 g of crude. The crude was purified by silica-gel (100-200 mesh) column chromatography eluting in only hexane. Solvent was evaporated under vacuum to afford 62.4 g of Nl-methyl-Nl,N4-bis(4-methylpentan-2-yl)benzene-l,4-diamine (25 % yield, >98 % pure by HPLC 260 nm, Mass (m / z): 291.33 [M+H]+) as a brown liquid.JH NMR (400 MHz, DMSO-tfc): 6 6.62 (d, J= 8.8 Hz, 2H), 6.46 (d, J= 8.8 Hz, 2H), 4.51 (d, J= 8.8 Hz, 1H), 3.8-3.63 (m, 1H), 3.31-3.28 (m, 1H), 2.47 (s, 3H), 1.75-1.68 (m, 1H), 1.61- 1.54 (m, 1H), 1.49-1.37 (m, 2H), 1.18-1.11 (m, 2H), 1.02 (d, J= 6.0 Hz, 3H), 0.92-0.84 (m, 15H).13C NMR (100 MHz, DMSO-tfc): 6 141.69, 140.52, 116.52, 115.42, 113.69, 52.65, 46.13, 42.92, 30.27, 24.50, 22.90, 22.77, 22.54, 22.37, 20.80, 15.80.EXAMPLE 22Synthesis of Nl-cyclohexyl-Nl-ethyl-N4-phenylbenzene-l,4-diamine (Compound 18)

[0198] To a stirred solution of Nl-cyclohexyl-N4-phenylbenzene-l,4-diamine (90.0 g, 0.338 mol) in DMF (450.0 mL, 5.0 vol) was added potassium carbonate (70.0 g, 0.507 mol) at RT. After stirring for 15-20 min at RT, the reaction was cooled to 0-5°C and ethyl iodide(32.3 mL, 0.406 mol) was added dropwise over a period of 45-60 min. The resulting reaction mixture was allowed to stir at RT for 48 h. After completion of reaction (monitored by TLC), the reaction was quenched with chilled water and extracted with ethyl acetate (900.0 mL). The organic layer was washed with a brine solution (500.0 mL). The organic layer was dried over sodium sulfate, filtered and solvent was evaporated under reduced pressure at 40-45°C to afford 142.0 g of crude. The crude was purified by silica-gel (100- 200 mesh) column chromatography eluting with 1-3% ethyl acetate in hexane. Solvent was evaporated under vacuum to afford 53.0 g of Nl-cyclohexyl-Nl-ethyl-N4-phenylbenzene- 1,4-diamine (68 % yield, >99 % pure by HPLC 260 nm, Mass (m / z): 295.24 [M+H]+) as an off-white solid. 'HNMR (400 MHz, DMSO-tfc): 67.58 (s, 1H), 7.10 (t, J= 8.0 Hz, 2H), 6.96 (d, J= 8.8 Hz, 2H), 6.83 (d, J= 8.4 Hz, 2H), 6.79 (d, J= 8.8 Hz, 2H), 6.62 (t, J= 7.6 Hz, 1H), 3.41-3.37 (m, 1H), 3.19 (q, J= 6.8 Hz, 2H), 1.77-1.72 (m, 4H), 1.63-1.59 (m, 1H), 1.42-1.28 (m, 4H), 1.16-1.13 (m, 1H), 1.04 (t, J= 6.8 Hz, 3H).13C NMR (100 MHz, DMSO- d6. 5 146.12, 143.34, 132.06, 128.91, 121.70, 117.26, 114.56, 113.94, 57.34, 38.90, 30.18, 25.65, 25.49, 15.02.EXAMPLE 23Synthesis of N1 -ethyl-N 1 -(4-methylpentan-2-yl)-N4-phenylbenzene- 1 ,4-diamine (Compound 11)

[0199] To a stirred solution of Nl-(4-methylpentan-2-yl)-N4-phenylbenzene-l,4-diamine (200.0 g, 0.745 mol)inDMF (LOL, 5.0 vol) was added potassium carbonate (154.4g, 1.117 mol) at RT. After stirring for 15-20 min at RT, the reaction was cooled to 0-5°C and ethyl iodide (72.0 mL, 0.894 mol) was added dropwise for 45-60 min. The resulting reaction contents were stirred at RT for 48 h. After completion of reaction (monitored by TLC), the reaction was quenched with chilled water and extracted with ethyl acetate (1.0 L). The organic layer was washed with brine solution (500.0 mL), dried over sodium sulfate, filtered and solvent was evaporated reduced pressure at 40-45°C to afford 420.0 g of crude. The crude was purified by silica-gel (100-200 mesh) column chromatography eluting with 1-3% ethyl acetate in hexane. Solvent was evaporated under vacuum to afford N1 -ethyl-Nl-(4-methylpentan-2-yl)-N4-phenylbenzene-l,4-diamine (41 % yield, >98 % pure by HPLC 260 nm, Mass (m / z): 297.12 [M+H]+) as a brown liquid. 'H NMR (400 MHz, DMSO-tfc): 67.59 (s, 1H), 7.11 (dd, J= 8.4, 7.6 Hz, 2H), 6.96 (d, J= 8.8 Hz, 2H), 6.84 (d, J= 8.4 Hz, 2H), 6.72 (d, J= 7.2 Hz, 2H), 6.63 (t, J= 7.2 Hz, 1H), 6.18 (d, J= 7.2 Hz, 1H), 3.80 (q, J= 6.4 Hz, 1H), 3.21-3.07 (m, 2H), 1.63-1.53 (m, 1H), 1.52-1.46 (m, 1H), 1.26- 1.19 (m, 1H), 1.09-1.02 (m, 6H), 0.91 (d, J= 6.0 Hz, 3H), 0.87 (d, J= 6.4 Hz, 3H).13CNMR (100 MHz, DMSO-tL): 6 146.01, 143.62, 132.18, 128.88, 121.50, 117.29, 114.91, 114.01, 51.70, 43.50, 37.04, 24.60, 22.69, 22.65, 17.59, 14.34.EXAMPLE 24Synthesis of Nl-cyclohexyl-Nl-ethyl-N4-phenylbenzene-l,4-diamine (Compound 26)

[0200] To a stirred solution of Nl-cyclohexyl-N4-phenylbenzene-l,4-diamine (200.0 g, 0.751 mol) in DMF (2.0 L, 10.0 vol) was added potassium carbonate (518.0 g, 3.75 mol) at RT. After stirring for 15-20 min at RT, cooled to 0-5°C and 2-iodopropane (375.0 mL, 3.75 mol) was added dropwise over a period of 45-60 min. The resulting reaction contents were heated at 80-85°C and stirred for 96 h. After completion of reaction (monitored by TLC), the reaction was cooled to RT, quenched with chilled water and extracted with ethyl acetate (1.5 L). The organic layer was washed with brine solution (800.0 mL), dried over sodium sulfate, filtered and solvent was evaporated under reduced pressure at 40-45°C to afford 350.0 g of crude. The crude was purified by silica-gel (100-200 mesh) column chromatography eluting with 2-4% ethyl acetate in hexane. Solvent was evaporated under vacuum to afford 95.0 g ofNl-cyclohexyl-Nl-ethyl-N4-phenylbenzene-l,4-diamine (41 % yield, >98 % pure by HPLC 260 nm, Mass (m / z): 309.30 [M+H]+) as a pale-brown semisolid.XH NMR (400 MHz, DMSO-tfc): 67.86 (s, 1H), 7.16 (t, J= 7.6 Hz, 2H), 6.95 (d, J= 8.8 Hz, 4H), 6.87 (d, J= 8.8 Hz, 2H), 6.71 (t, J= 7.2 Hz, 1H), 3.61-3.54 (m, 1H), 3.09- 3.07 (m, 1H), 1.72-1.68 (m, 4H), 1.55-1.52 (m, 1H), 1.31-1.18 (m, 4H), 1.09-1.07 (m, 1H), 1.02 (d, J=6.4Hz, 6H).13C NMR (100 MHz, DMSO-tfc): 6 144.72, 140.62, 137.06, 129.01, 125.40, 118.34, 118.29, 115.24, 56.74, 47.26, 31.38, 25.71, 25.32, 21.41.EXAMPLE 25Synthesis of N1 -ethyl-N 1 ,N4-bis(4-methylpentan-2-yl)benzene- 1 ,4-diamine (Compound14)

[0201] To a stirred solution of Nl,N4-bis(4-methylpentan-2-yl)benzene-l,4-diamine (100.0 g, 0.362 mol) in DMF (500.0 L, 5.0 vol) was added potassium carbonate (100.0 g, 0.724 mol) at RT. After stirring for 15-20 min at RT, ethyl iodide (23.3 mL, 0.289 mol) was added dropwise for 45-60 min and the resulting reaction contents were stirred at RT for 32 h. After completion of reaction (monitored by TLC), the reaction was quenched with chilled water and extracted with ethyl acetate (500.0 mL). The separated organic layer was washed with brine solution (500.0 mL), dried over sodium sulfate, filtered and solvent was evaporated under reduced pressure at 40-45°C to afford 120.0 g of crude. The crude compound was purified by silica-gel (100-200 mesh) column chromatography eluting in 1- 3% ethyl acetate in hexane. Solvent was evaporated under vacuum to afford 33.0 g of Nl- ethyl-Nl,N4-bis(4-methylpentan-2-yl)benzene-l,4-diamine (30 % yield, >98 % pure by HPLC 260 nm, Mass (m / z): 305.38 [M+H]+) as a brown liquid. 'H NMR (400 MHz, Acetone-tfc): 66.60 (d, J= 8.8 Hz, 2H), 6.41 (d, J= 8.8 Hz, 2H), 3.80 (s, 1H), 3.43-3.30 (m, 2H), 2.91 (q, J= 6.8 Hz, 2H), 1.70-1.58 (m, 2H), 1.42-1.31 (m, 2H), 1.13-1.06 (m, 1H), 1.04-0.99 (m, 1H), 0.97 (d, J= 6.0 Hz, 3H), 0.87-0.84 (m, 6H), 0.80-0.76 (m, 12H).13C NMR (100 MHz, Acetone-tL): 6 142.71, 140.89, 121.09, 114.86, 55.73, 47.72, 47.69, 45.07, 39.28, 25.81, 25.78, 23.38, 23.23.EXAMPLE 26Synthesis of Nl,N4-bis(5,5-dimethylhexan-2-yl)-Nl-methylbenzene-l,4-diamine (Compound 21)Step 1: Synthesis of 5,5 -dimethylhex-3-en-2-one:

[0202] To a stirred solution of diethyl (2-oxopropyl) phosphonate (669.6 mL, 3.48 mol) in THF (1.0 L, 10.0 vol) was added potassium tert-butoxide (390.8 g, 3.48 mol) portion-wise for 30-45 min at 15-20°C. The resulting reaction mixture was warmed to RT and stirred for 1 h. Pivaldehyde (100.0 g, 1.16 mol) was added portion wise over a period of 30-45 min at RT and stirred for 16 h. After completion of reaction (monitored by TLC), the reaction was quenched with ice-cold water and extracted with diethyl ether (1.0 L). The separated organic layer was dried over sodium sulfate, filtered and evaporated under vacuum to afford 175.0 g of crude as a brown liquid. The crude was purified by vacuum distillation at 95- 100°C, to afford 60.0 g of 5,5-dimethylhex-3-en-2-one as a colorless oil.Step 2: Synthesis of Nl,N4-bis(5,5-dimethylhexan-2-yl)benzene-l,4-diamine

[0203] To a stirred solution of paraphenylenediamine (100.0 g, 0.924 mol) in IPA (1.0 L, 10.0 vol) was added 5,5-dimethylhex-3-en-2-one (268.0 g, 2.126 mol), followed by 5% Pt / C (10.0 g, 10% w / w) at RT in an autoclave. Hydrogen pressure (300 psi) was applied and the resulting reaction contents were heated at 100-105°C and stirred for 16 h. After completion of reaction (monitored by TLC), the reaction was cooled to RT and filtered through a celite bed (washed with IPA 300.0 mL). Solvent was evaporated under vacuum to afford 310.0 g of crude compound. The crude was purified by silica-gel (100-200 mesh) column chromatography eluting with 4-7% ethyl acetate in hexane. Solvent was evaporated under vacuum to afford compound Nl,N4-bis(5,5-dimethylhexan-2-yl)benzene-l,4- diamine as a brown semisolid.Step 3: Synthesis of Nl,N4-bis(5,5-dimethylhexan-2-yl)-Nl -methylbenzene- 1,4-diamine:

[0204] To a stirred solution of Nl,N4-bis(5,5-dimethylhexan-2-yl)benzene-l,4-diamine (100.0 g, 0.300 mol) in DMF (1.0 L, 10.0 vol) was added potassium carbonate (103.0 g, 0.746 mol) at RT. The reaction mixture was stirred for 10-15 min at RT and cooled to 0- 5°C, followed by addition of methyl iodide (22.4 mL, 0.360 mol) dropwise over a period of 10-15 min. The resulting reaction mixture was warmed to RT and stirred for 6 h. After completion of the reaction (monitored by TLC), the reaction was quenched with ice cold water and extracted with ethyl acetate (1.0 L). The separated organic layer was dried over Na2SC>4, filtered and evaporated under reduced pressure to afford 125.0 g of crude. The crude was purified by column chromatography using silica gel (100-200 mesh) as the stationary phase, eluting with 2-5% ethyl acetate in hexane. Solvent was evaporated under reduced pressure to afford desired 61.5 g of Nl,N4-bis(5,5-dimethylhexan-2-yl)-Nl- methylbenzene- 1,4-diamine (59 % yield, >97 % pure by HPLC 260 nm, Mass (m / z): 347.53 [M+H]+) as a brown liquid. 'H NMR (400 MHz, DMSO-tfc): 6 6.60 (d, J= 8.8 Hz, 2H), 6.45 (d, J= 8.8 Hz, 2H), 4.53 (d, J= 8.8 Hz, 1H), 3.51-3.43 (m, 1H), 3.21-3.16 (m, 1H), 2.50 (s, 3H), 1.49-1.43 (m, 2H), 1.32-1.09 (m, 6H), 1.04 (d,J= 6.4 Hz, 3H), 0.94 (d,J= 6.4 Hz, 3H), 0.85 (s, 18H). 'H NMR (400 MHz, Pyridine-^): 66.94 (d, J= 8.4 Hz, 2H), 6.86 (d, J= 8.4 Hz, 2H), 4.57 (s, 1H), 3.65-3.61 (m, 1H), 3.41 (m, 1H), 2.61 (s, 3 H), 1.63-1.53 (m, 2H), 1.41-1.30 (m, 4H), 1.27-1.16 (m, 5H), 1.01 (d, J= 6.8 Hz, 3H), 0.86 (s, 9H), 0.84 (s,9H).13C NMR (100 MHz, DMSO-tfc): 6 141.87, 140.41, 116.50, 113.76, 55.70, 48.89, 40.77, 40.17, 39.98, 31.25, 30.33, 29.88, 29.24, 28.69, 20.50, 16.05.13C NMR (100 MHz, Pyridine-tZs): 8 143.90, 141.91, 118.13, 115.35, 57.29, 50.56, 41.97, 41.22, 32.77, 31.24, 30.68, 30.65, 30.08, 29.97, 29.93, 21.51, 17.73.EXAMPLE 27Synthesis of Nl,N4-bis(5,5-dimethylhexan-2-yl)-Nl,N4-dimethylbenzene-l,4-diamine (Compound 50)

[0205] To a stirred solution of Nl,N4-bis(5,5-dimethylhexan-2-yl)benzene-l,4-diamine (50.0 g, 0.300 mol) in DMF (500.0 mL, 10.0 vol) was added potassium carbonate (51.8 g, 0.375 mol) at RT. After stirring for 15 min, the reaction was cooled to 0-5°C and then methyl iodide was added dropwise (18.7 mL, 0.300 mol). The resulting reaction contents were allowed to stir at RT for 6 h. After completion of the reaction (monitored by TLC), the reaction was quenched with ice cold water and extracted with ethyl acetate (500.0 mL). The separated organic layer was dried over Na2SC>4, filtered and solvent was evaporated under reduced pressure to afford 62.0 g of crude. The crude was purified by column chromatography using silica gel (100-200 mesh) as the stationary phase, eluting with 1-3% ethyl acetate in hexane. Solvent was evaporated under reduced pressure to afford desired 18.0 g of Nl,N4-bis(5,5-dimethylhexan-2-yl)-Nl,N4-dimethylbenzene-l,4-diamine (33 % yield, >98 % pure by HPLC 260 nm, Mass (m / z): 361.39 [M+H]+) as a pink solid. 'H NMR. (400 MHz, Pyridine-d5): 86.98 (s, 4H), 3.75-3.67 (m, 1H), 2.63 (s, 6H), 1.61-1.53 (m, 2H), 1.39-1.29 (m, 4H), 1.23-1.15 (m, 2H), 1.02 (d, J= 6.0 Hz, 6H), 0.86 (s, 18H). 13C NMR (100 MHz, Pyridine-d5): 6 144.22, 116.90, 56.50, 41.84, 30.85, 30.57, 30.00, 29.85, 16.87.EXAMPLE 28Synthesis of Nl-methyl-Nl,N4-di-o-tolylbenzene-l,4-diamine (Compound 46)

[0206] To a stirred solution of Nl,N4-di-o-tolylbenzene-l,4-diamine (120.0 g, 0.416 mol) in DMF (600.0 mL, 5.0 vol) was added potassium carbonate (86.0 g, 0.624 mol) at RT. After stirring for 15-20 min at RT, the reaction was cooled to 0-5°C and methyl iodide (31.0 mL, 1.2 mol) was added dropwise for 45-60 min. The resulting reaction mixture was warmed to RT and stirred for 48 h. After -50% completion of reaction (monitored by TLC),the reaction was cooled to RT, quenched with chilled water and extracted with ethyl acetate (1.0 L). The separated organic layer was washed with brine solution (1.0 L), the organic layer was dried over sodium sulfate, filtered and solvent was evaporated under reduced pressure at 40-45°C to afford 128.0 g of crude. The crude was purified by silica-gel (100- 200 mesh) column chromatography eluting in 0-2% ethyl acetate in hexane. Solvent was evaporated under vacuum to afford Nl-methyl-Nl,N4-di-o-tolylbenzene-l,4-diamine (19 % yield, >96 % pure by HPLC 260 nm, Mass (m / z): 303.20 [M+H]+) as a brown semisolid. 'H NMR (400 MHz, DMSO-tfc): 6 7.29-7.24 (m, 2H), 7.17-7.12 (m, 2H), 7.06 (d, J= 7.6 Hz, 1H), 6.96 (d, J= 7.2 Hz, 1H), 6.91-6.81 (m, 4H), 6.67-6.63 (m, 1H), 6.47 (d, J= 8.8 Hz, 2H), 3.14 (s, 3H), 2.17 (s, 3H), 2.08 (s, 3H).13C NMR (100 MHz, DMSO-tfc): 6 147.04, 144.05, 144.02, 135.39, 134.18, 131.21, 130.47, 127.47, 126.90, 126.31, 125.61, 125.22, 121.48, 118.68, 114.59, 114.29, 17.99, 17.74.EXAMPLE 29Synthesis of Nl,N4-dicy cl ohexyl-Nl -ethylbenzene- 1,4-diamine (Compound 12)

[0207] To a stirred solution of Nl,N4-di cyclohexylbenzene- 1,4-diamine (950.0 g, 3.492 mol) in DMF (4.7 L, 5.0 vol) was added potassium carbonate (718.2 g, 5.23 mol) at RT. After stirring for 15-20 min at RT, the reaction mass was cooled to 0-5°C and ethyl iodide (279.3 mL, 3.49 mol) was added dropwise over a period of 60-90 min. The resulting reaction mixture was warmed to RT and stirred at RT for 16 h. After completion of reaction (monitored by TLC), the reaction was quenched with chilled water and extracted with ethyl acetate (5.0 L). The separated organic layer was washed with brine solution (2.5 L), the organic layer was dried over sodium sulfate, filtered and solvent was evaporated under reduced pressure at 40-45°C to afford 1200.0 g of crude. The crude was purified by silica- gel (100-200 mesh) column chromatography eluting with 3-5% ethyl acetate in hexane. Solvent was evaporated under vacuum to afford 325.0 g of Nl, N4-dicy cl ohexyl-Nl - ethylbenzene- 1,4-diamine (31 % yield, >99 % pure by HPLC 260 nm, Mass (m / z): 301.4 [M+H]+) as a brown liquid. 'HNMR (400 MHz, DMSO ): 66.63 (d, J= 8.8 Hz, 2H), 6.46 (d, J= 8.8 Hz, 2H), 4.71 (s, 1H), 3.02 (q, J= 6.8 Hz, 4H), 1.90-1.87 (m, 2H), 1.72-1.67 (m,6H), 1.59-1.54 (m, 2H), 1.35-1.02 (m, 10H), 0.91 (t, J= 6.8 Hz, 3H).13C NMR (100 MHz, DMSO-tL): 6 141.47, 138.45, 120.42, 113.32, 59.69, 51.24, 40.85, 32.83, 30.23, 25.63, 25.48, 24.56, 14.53.EXAMPLE 30Synthesis of Nl,N4-dimethyl-Nl,N4-bis(4-methylpentan-2-yl)benzene-l,4-diamine (Compound 33)

[0208] To a stirred solution of Nl,N4-bis(4-methylpentan-2-yl)benzene-l,4-diamine (150.0 g, 0.543 mol) inDMF (750.0 mL, 5.0 vol) was added potassium carbonate (150.0 g, 1.08 mol) at RT. After stirring for 15-20 min at RT, the reaction was cooled to 0-5°C and methyl iodide (33.6 mL, 0.543 mol) was added dropwise for 45-60 min. The resulting reaction mixture was allowed to stir at RT for 16 h. After completion of reaction (monitored by TLC), the reaction was quenched with chilled water and extracted with ethyl acetate (1.0 L). The separated organic layer was washed with brine solution (1.0 L), the organic layer was dried over sodium sulfate, filtered and solvent was evaporated under reduced pressure at 40-45°C to afford 206.0 g of crude. The crude was purified by silica-gel (100- 200 mesh) column chromatography eluting in 0-2% ethyl acetate in hexane. Solvent was evaporated under vacuum to afford Nl,N4-dimethyl-Nl,N4-bis(4-methylpentan-2- yl)benzene-l,4-diamine (54 % yield, >97 % pure by HPLC 260 nm, Mass (m / z): 305.34 [M+H]+) as abrown liquid. *HNMR (400 MHz, Pyridine-tZs): 86.95 (s, 4H), 3.92-3.84 (m, 2H), 2.59 (s, 6H), 1.69-1.59 (m, 2H), 1.54-1.47 (m, 2H), 1.17-1.09 (m, 2H), 0.98 (d,J=6.4 Hz, 6H), 0.87 (d, J= 6.4 Hz, 12H).13C NMR (100 MHz, Pyridine-^): 6 144.02, 116.82, 53.31, 44.04, 30.85, 25.61, 23.56, 23.01, 16.76.EXAMPLE 31Synthesis of N1 -isopropyl-N 1 ,N4-bis(4-methylpentan-2-yl)benzene- 1 ,4-diamine (Compound 29) and Nl,N4-diisopropyl-Nl,N4-bis(4-methylpentan-2-yl)benzene-l,4- diamine (Compound 55)

[0209] To a stainless steel autoclave was charged Nl,N4-bis(4-methylpentan-2- yl)benzene-l,4-diamine (75.0 g, 1 Eq, 271 mmol), 2,2-dimethoxypropane (45.2 g, 1.6 Eq, 434 mmol), propan-2-ol (16.3 g, 100 mL, 1 Eq, 271 mmol), 501.4 mg of 3% Pt / C / sulfided, and finally methanesulfonic acid (1.30 g, 0.87 mL, 0.05 Eq, 13.6 mmol). This reaction was equipped to a Paar hydrogenator and the atmosphere was exchanged for nitrogen and then hydrogen through successive fill / release cycles (3 / gas). The pressure was reduced to 21 psi of H2 and the autoclave was heated to 140 °C while stirring at 1500 RPM. Once the temperature was stable, a constant pressure of hydrogen was applied (600 psi), and the mixture was allowed to stir at this temperature and pressure for 4h 30 min. Upon cooling to room temperature, the resulting mixture was analyzed by HPLC. The solvent was removed by rotary evaporation and the resulting oil was dissolved in MTBE and transferred to a separatory funnel and 100 ml of water was added. The organic layer was washed with water (2xl00mL), saturated aq. sodium bicarbonate (lx50mL), water (lOOmL), and brine (50mL) before drying over sodium sulfate. The desiccant was removed by filtration and the filtrate was concentrated by rotary evaporation. The crude oil was purified by flash column chromatography (deactivated silica gel directly before use with TEA, column run in 0.5% TEA in hexanes to remove starting material. Then, a second column was run in 5% EA / Hexanes to afford ~40 grams of pure product. The resulting impure fractions were combined and chromatographed again with 5% EA in hexanes to separate the remaining product. All pure fractions were combined and concentrated to afford the Nl-isopropyl- Nl,N4-bis(4-methylpentan-2-yl)benzene-l,4-diamine as a thin, amber oil (52.6 g, 165 mmol, 60.9 %yield) andNl,N4-diisopropyl-Nl,N4-bis(4-methylpentan-2-yl)benzene-l,4- diamine as a yellow oil (21.2 g, 58.8 mmol, 21.7 % yield).

[0210] N 1 -isopropyl-N 1 ,N4-bis(4-methylpentan-2-yl)benzene- 1 ,4-diamine (Compound 29): 'H NMR (81 MHz, TFA) 8 7.32 (s, 4H), 4.37 - 2.77 (m, 3H), 1.47 - 0.14 (m, 30H).13C NMR (20 MHz, TFA) 6 135.53, 135.28, 125.93, 125.39, 60.95, 57.70, 41.06, 38.44, 24.00, 21.75, 21.27, 18.90, 18.63, 17.02, 16.30, 15.49, 14.88, 14.47, 12.24, 12.01.

[0211] Nl,N4-diisopropyl-Nl,N4-bis(4-methylpentan-2-yl)benzene-l,4-diamine (Compound 55): *HNMR (81 MHz, Neat) 66.69 (s, 4H), 4.21 - 2.86 (m, 4H), 2.37 - 0.19(m, 36H).13C NMR (20 MHz, Neat) 5 115.13, 97.22, 25.47, 23.04, 19.75, -0.14, -2.84, -3.72, -6.86.EXAMPLE 32Oxidative Induction Time (OIT) Performance of Compounds of the Disclosure

[0212] The oxidative induction time (OIT) of representative Compounds of the Disclosure was evaluated. OIT is measured according to a procedure carried out in a differential scanning calorimeter (DSC; TA Instruments, Q200). In this procedure, a sample is held in a cell and heated under a nitrogen atmosphere to a preselected temperature. Oxygen (O2) is then introduced to the cell and the length of time before the onset of degradation, as observed by the initiation of an endothermic process in the DSC trace, is measured.

[0213] 0.5 wt % of a Compound of the Disclosure or 7V1-(4.methylpentan-2-yl)-A4- phenylbenzene-l,4-diamine (6PPD) was mixed with polyisoprene and heated isothermally at 150 °C or 160 °C in O2. The OIT in minutes is shown in Table 6. As indicated by the data in Table 6, Compounds of the Disclosure demonstrate antioxidant activity.Table 6

[0214] In another test, 0.5 wt % of a Compound of the Disclosure or ^-(d-methylpentan- 2-yl)-A4-phenylbenzene-l,4-diamine (6PPD) was mixed with polyisoprene and heated isothermally at 150 °C or 160 °C in O2. The OIT in minutes is shown in Table 7. As indicated by the data in Table 7, Compounds of the Disclosure demonstrate antioxidant activity.Table 7

[0215] In another test, 0.5 wt % of a Compound of the Disclosure or ^-(d-methylpentan- 2-yl)-A4-phenylbenzene-l,4-diamine (6PPD) was mixed with polyisoprene and heated isothermally at 150 °C or 160 °C in O2. The OIT in minutes is shown in Table 8. Asindicated by the data in Table 8, Compounds of the Disclosure demonstrate antioxidant activity.Table 8

[0216] In another test, 0.5 wt % of a Compound of the Disclosure or A1-(4-methylpentan- 2-yl)-A4-phenylbenzene-l,4-diamine (6PPD) was mixed with polyisoprene and heated isothermally at 150 °C or 160 °C in O2. The OIT in minutes is shown in Table 9. As indicated by the data in Table 9, Compounds of the Disclosure demonstrate antioxidant activity.Table 9

[0217] In another test, 0.5 wt % of a Compound of the Disclosure or A1-(4-methylpentan- 2-yl)-A4-phenylbenzene-l,4-diamine (6PPD) was mixed with polyisoprene and heated isothermally at 150 °C or 160 °C in O2. The OIT in minutes is shown in Table 10. As indicated by the data in Table 10, Compounds of the Disclosure demonstrate antioxidant activity.Table 10

[0218] In another test, 0.5 wt % of a Compound of the Disclosure or A1-(4-methylpentan- 2-yl)-A4-phenylbenzene-l,4-diamine (6PPD) was mixed with polyisoprene and heated isothermally at 150 °C or 160 °C in O2. The OIT in minutes is shown in Table 11. As indicated by the data in Table 11, Compounds of the Disclosure demonstrate antioxidant activity.Table 11

[0219] In another test, 0.5 wt % of a Compound of the Disclosure or A1-(4-methylpentan- 2-yl)-A4-phenylbenzene-l,4-diamine (6PPD) was mixed with polyisoprene and heated isothermally at 150 °C or 160 °C in O2. The OIT in minutes is shown in Table 12. As indicated by the data in Table 12, Compounds of the Disclosure demonstrate antioxidant activity.Table 12

[0220] In another test, 0.5 wt % of a Compound of the Disclosure or ^-(d-methylpentan- 2-yl)-A4-phenylbenzene-l,4-diamine (6PPD) was mixed with polyisoprene and heatedisothermally at 150 °C or 160 °C in O2. The OIT in minutes is shown in Table 13. As indicated by the data in Table 13, Compounds of the Disclosure demonstrate antioxidant activity.Table 13

[0221] In another test, 0.5 wt % of a Compound of the Disclosure or A1-(4-methylpentan- 2-yl)-A4-phenylbenzene-l,4-diamine (6PPD) was mixed with polyisoprene and heated isothermally at 150 °C or 160 °C in O2. The OIT in minutes is shown in Table 14. As indicated by the data in Table 14, Compounds of the Disclosure demonstrate antioxidant activity.Table 14

[0222] In another test, 0.5 wt % of a Compound of the Disclosure or ^-(d-methylpentan- 2-yl)-A4-phenylbenzene-l,4-diamine (6PPD) was mixed with polyisoprene and heated isothermally at 150 °C or 160 °C in O2. The OIT in minutes is shown in Table 15. As indicated by the data in Table 15, Compounds of the Disclosure demonstrate antioxidant activity.Table 15

[0223] In another test, 0.5 wt % of a Compound of the Disclosure or Afl-(4-methylpentan- 2-yl)-A4-phenylbenzene-l,4-diamine (6PPD) was mixed with polyisoprene and heated isothermally at 150 °C or 160 °C in O2. The OIT in minutes is shown in Table 16. Asindicated by the data in Table 16, Compounds of the Disclosure demonstrate antioxidant activity.Table 16

[0224] In another test, 0.5 wt % of a Compound of the Disclosure or / ^-(d-methylpentan- 2-yl)-A4-phenylbenzene-l,4-diamine (6PPD) was mixed with polyisoprene and heated isothermally at 150 °C or 160 °C in O2. The OIT in minutes is shown in Table 17. As indicated by the data in Table 17, Compounds of the Disclosure demonstrate antioxidant activity.Table 17EXAMPLE 33Use of Compounds of the Disclosure in Tread Formulations

[0225] Rubber compounds were prepared using Compounds of the Disclosure or VJ-(4- m ethyl pentan- -ylJ-Mhphenylbenzene-IA-diamine (6PPD) as anti degradants in tread formulations. As shown in Tables 18-20, the rubber compounds are a 70 / 30 blend of styrene-butadiene rubber and butadiene rubber with silica and carbon black. According to American Society for Testing Materials (ASTM) test method D5289, vulcanization properties of all the compounds were characterized by a moving die rheometer (Alpha Technologies MDR 2000 and Alpha Technologies Premier MDR), also known as MDR, at a temperature of 170 °C for 30 minutes. The oscillation strain and frequency were set to 0.5 °C and 1.667 Hz, respectively. The MDR test results were summarized in Tables 21-23 and and are shown on a normalized basis relative to samples containing 6PPD (Example 17). For example, MH rel for Example 1 is (MH_Examplel / MH_Examplel7)><100%.Table 18Table 198*8*PD = Nl,N4-bis(5,5-dimethylhexan-2-yl)benzene-l,4-diamineTable 20Table 21Table 22Table 23EXAMPLE 34Antiozonant Performance of Compounds of the Disclosure in Tread Compounds

[0226] Each of the rubber compounds prepared in Example 33 (Rubber Compound Examples 1-29) were cured at 170 °C to a state equivalent to its T90+2 min time. The ozone test specimens were died out from vulcanized tensile sheets by using a die followed the American Society for Testing and Materials. (ASTM) DI 329 standard. The ozone testspecimens were stored in an ambient environment for more than 24 hours prior to antiozonant performance testing in an ozone chamber, which was maintained at an ozone concentration of 10 ± 2 parts per hundred million (pphm) and 40 ± 2 °C. The ozone test specimens were simultaneously relaxed and extended within ozone chamber under dynamic conditions. The ozone test specimens extended to 25% strain at a rate of 90 cycles per minute during dynamic exposure. Samples were exposed to ozone for 96hours followed by at least one hour of relaxation after removal from the ozone chamber and prior to measurement of force at a strain of 100%.

[0227] Antiozonant performance of antidegradant formulated compounds were evaluated by percentage of force retention relative to 6PPD. The percentage of force retention relative to 6PPD in Example 17 is defined by Equation 1.Equation 1. Percentage of relative force retention = (F_Example / F0_Example) / (F_6PPD / F0_6PPD) x 100%wherein FO Example is the force at a strain of 100% prior to ozone testing andF Example is the force at a strain of 100% after samples are aged in ozone chamber for 96-hour cycle at dynamic exposure, while F 6PPD and F0 6PPD are the corresponding values for the specimens of Example 17. Higher percentage of relative force retention is an indication of better antiozonant performance of an antidegradant compound incorporated in the vulcanized rubber compound. Any value over 100% is a sample that exceeds the performance of 6PPD after ozone exposure.

[0228] The force of unaged and ozone aged test specimens was measured by using a Universal Tester (Instron) at a strain of 100%. The percentage of relative force retention were calculated and tabulated in Table 24.Table 24

[0229] Having now fully described the methods, compounds, and compositions herein, it will be understood by those of skill in the art that the same can be performed within a wide and equivalent range of conditions, formulations, and other parameters without affecting the scope of the methods, compounds, and compositions provided herein or any embodiment thereof. All patents, patent applications, and publications cited herein are fully incorporated by reference herein in their entirety.

Claims

What is claimed is:

1. A compound having Formula (II):or a salt, solvate, or stereoisomer thereof, wherein:R1is selected from the group consisting of C1-C12 alkyl and Cs-Cs cycloalkyl;Rlais C1-C4 alkyl or -C(=O)CH3;R2a, R2b, R2c, and R2dare each independently selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, Cs-Cs cycloalkyl, Ci-Cs alkoxy, and Ci-Cs alkylthio; andR3is selected from the group consisting of C1-C12 alkyl, Cs-Cs cycloalkyl, and optionally substituted phenyl;with the proviso that when Rlais methyl, R2a, R2b, R2c, and R2dare hydrogen, and R3is phenyl, then R1is C4-C12 alkyl.

2. The compound of claim 1, or a salt or solvate thereof, wherein R2a, R2b, R2c, and R2dare each hydrogen or C1-C9 alkyl.

3. The compound of claim 2, or a salt or solvate thereof, wherein R2a, R2b, R2c, and R2dare each hydrogen.

4. The compound of any one of claims 1-3, or a salt or solvate thereof, wherein R1is C1-C12 alkyl.

5. The compound of claim 4, or a salt or solvate thereof, wherein R1is selected from the group consisting of:

6. The compound of any one of claims 1-3, or a salt or solvate thereof, wherein R1is C3-C8 cycloalkyl.

7. The compound of claim 6, or a salt or solvate thereof, wherein R1is:

8. The compound of any one of claims 1-7, or a salt or solvate thereof, wherein Rlais methyl or ethyl.

9. The compound of claim 8, or a salt or solvate thereof, wherein Rlais methyl.

10. The compound of any one of claims 1-9, or a salt or solvate thereof, wherein R3is phenyl.

11. The compound of any one of claims 1-9, or a salt or solvate thereof, wherein R3is C1-C12 alkyl.

12. The compound of any one of claims 1-9, or a salt or solvate thereof, wherein R3is Cs-Cs cycloalkyl.

13. The compound of claim 12, or a salt or solvate thereof, wherein R3is:

14. The compound of claim 1, or a salt or solvate thereof, selected from any one or more of the compounds of Table 1.

15. A compound selected from any one or more of the compounds of Table 2, or a salt or solvate thereof.

16. A composition comprising:(i) the compound of any one of claims 1-15; and(ii) one or more elastomers; or(iii) one or more fillers; or(iv) one or more rubber chemicals; or(v) one or more plasticizers; or(vi) one or more additional anti degradants; or(vii) a combination of one or more elastomers, one or more fillers, one or more rubber chemicals, one or more plasticizers, and / or one or more additional anti degradants.

17. A composition comprising:(i) any one or more of the compounds of Table 3, or a salt or solvate thereof; and(ii) one or more elastomers; or(iii) one or more fillers; or(iv) one or more rubber chemicals; or(v) one or more plasticizers; or(vi) one or more additional anti degradants; or(vii) a combination of one or more elastomers, one or more fillers, one or more rubber chemicals, one or more plasticizers, and / or one or more additional anti degradants.

18. The composition of claim 16 or 17, wherein the composition comprises from about 0.1 wt / wt% to about 10 wt / wt% of the compound.

19. The composition of any one of claims 16-18, wherein the composition comprises one or more elastomers.

20. The composition of claim 17, wherein the composition comprises from about 0.1 wt / wt % to about 10 wt / wt % of the compound and from about 5 wt / wt % to about 95 wt / wt % of the one or more elastomers.

21. The composition of claim 17 or 18, wherein the one or more elastomers comprise natural rubber (NR).

22. The composition of claim 19, wherein the one or more elastomers comprises from about 5 wt / wt % to about 100 wt / wt % natural rubber (NR).

23. The composition of claim 19 or 20, wherein the natural rubber comprises rubber derived from an alternative rubber plant.

24. The composition of claim 21, wherein the alternative rubber plant is Parthenium argentatum (guayule) or Taraxacum kok-saghyz (Russian dandelion).

25. The composition of any one of claims 17-22, wherein the one or more elastomers comprise synthetic rubber.

26. The composition of claim 25, wherein the synthetic rubber comprises an unsaturated rubber, a saturated rubber, a rubber with fluoro and fluoralkyl or fluoralkoxy substituent groups on the polymer chain (FKM), a silicone rubber (Q), or a blend thereof.

27. The composition of claim 26, wherein the unsaturated rubber comprises polyisoprene rubber (IR), butyl rubber (IIR), polybutadiene rubber (BR), styrene butadiene rubber (SBR), nitrile butadiene rubber (NBR), chloroprene rubber (CR), ethylene propylene diene rubber (EPDM), or a blend thereof.

28. The composition of claim 27, wherein the unsaturated rubber comprises styrene butadiene rubber (SBR).

29. The composition of claim 28, wherein the one or more elastomers comprise from about 5 wt / wt % to about 100 wt / wt % styrene butadiene rubber (SBR).

30. The composition of any one of claims 25-27, wherein the unsaturated rubber comprises polybutadiene rubber (BR).

31. The composition of claim 30, wherein the one or more elastomers comprise from about 5 wt / wt % to about 80 wt / wt % polybutadiene rubber (BR).

32. The composition of any one of claims 25-27, wherein the unsaturated rubber comprises butyl rubber (IIR).

33. The composition of claim 32, wherein the one or more elastomers comprise from about 1 wt / wt % to about 30 wt / wt % butyl rubber (IIR).

34. The composition of any one of claims 20-26, wherein the saturated rubber comprises acrylic rubber (ACM), chlorinated polyethylene (CM), chlorosulfonated polyethylene (CSM), polychloromethyl oxirane (CO), ethylene-ethyl acrylate copolymer (EAM), epichlorohydrin rubber (ECO), ethylene propylene rubber (EPM), ethylenevinylacetate copolymer (EVM), or a blend thereof.

35. The composition of claims any one of claims 16-34, wherein the one or more elastomers further comprises recycled rubber.

36. The composition of any one of claims 19-35, wherein the composition comprises from about 0.1 phr to about 10 phr of the compound.

37. The composition of claim 36, wherein the composition comprises from about 0.5 phr to about 5 phr of the compound.

38. The compound of claim 37, wherein the composition comprises from about 1 phr to about 5 phr of the compound.

39. The composition of any one of claims 16-38, wherein the composition comprises one or more fillers.

40. The composition of claim 39, wherein the composition comprises from about 0.1 wt / wt % to about 10 wt / wt % of the compound and from about 5 wt / wt % to about 95 wt / wt % of the one or more fillers.

41. The composition of claims 39 or 40, wherein the composition comprises from about 30 phr to about 500 phr of one or more fillers.

42. The composition of any one of claims 39-41, wherein the one or more fillers comprise carbon black, silica, kaolin, calcium silicate, talc, carbon nanotubes (CNT), carbon fibers (HCF), graphite, graphenes, aluminosilicates, starch, fibers, or a combination thereof.

43. The composition of claim 42, wherein the one or more fillers comprise silica.

44. The composition of claim 43, wherein the silica is derived from rice husks.

45. The composition of any one of claims 39-42, wherein the one or more fillers comprise carbon black.

46. The composition of any one of claims 16-45, wherein the composition comprises one or more rubber chemicals.

47. The composition of claim 46, wherein the composition comprises from about 0.1 wt / wt % to about 10 wt / wt % of the compound and from about 5 wt / wt % to about 95 wt / wt % of one or more rubber chemicals.

48. The composition of claims 46 or 47, wherein the composition comprises from about 0.1 phr to about 30 phr of one or more rubber chemicals.

49. The composition of claim 48, wherein the composition comprises from about 1 phr to about 20 phr of one or more rubber chemicals.

50. The composition of any one of claims 46-49, wherein the one or more rubber chemicals comprise one or more vulcanizing agents, one or more accelerators, one or more activators, one or more pre-vulcanization inhibitors, or a combination thereof.

51. The composition of claim 50, wherein the one or more rubber chemicals comprise one or more vulcanizing agents.

52. The composition of claim 51, wherein the one or more vulcanizing agents comprise sulfur, peroxide, resin, or a combination thereof.

53. The composition of claim 52, wherein the sulfur is octasulfur (Ss), cyclododecasulfur (S12), polymeric sulfur, or a combination thereof.

54. The composition of claim 52, wherein the peroxide is benzoyl peroxide, dicumyl peroxide (DC), 2,5-dimethyl-2,5-di-(tert-butylperoxy)-3-hexyne (2,5 Tri), 2,5-dimethyl-2,5-di(tert-butylperoxy)hexane (DDPH), di-(2-tert-butylperoxyisopropyl)benzene (VC), butyl-4,4-di-(tert-butylperoxy)valerate (VAL), l,l-di(tert-butylperoxy)-3,3,5-trimethylcyclohexane (TMC), or a combination thereof.

55. The composition of claim 52, wherein the resin is a bonding resin.

56. The composition of claims 46-55, wherein the one or more rubber chemicals comprise one or more accelerators.

57. The composition of claim 56, wherein the one or more accelerators comprise a guanidine, a thiazole, a sulfenamide, a thiuram, a dithiocarbamate, a xanthate, a thiophosphate, or a combination thereof.

58. The composition of claim 57, wherein the guanidine is diphenylguanidine (DPG).

59. The composition of claim 57, wherein the thiazole comprises 2-mercaptobenzothiazole (MBT), zinc 2-mercaptobenzothiazole (ZMBT), mercaptobenzothiazole disulfide (MBTS), V- / ert-butyl-2-benzothi azole sulfenimide (TBSI), or a combination thereof.

60. The composition of claim 57, wherein the sulfenamide comprises A- / c / 7-butyl-2-benzothiazylsulfenamide (TBBS), 7V-cyclohexylbenzothiazol-2-sulfenamide (CBS), dicyclohexyl-2-benzothiazolesulfenamide (DCBS), A -oxy di ethylene benzothiazole sulfenamide (OBTS), N-oxy di ethylenethiocarbamyl- / ' / '-oxy di ethylene sulfenamide (OTOS), thiocarbamyl sulfenamide, or a combination thereof.

61. The composition of claim 57, wherein the thiuram is dimethylcarbamothioic dithioperoxyanhydride (thiram), dipentamethylene thiuram tetrasulfide (DPIT), tetrabenzyl thiuram disulfide (TBzTD), tetraethylthiuram disulfide (TETD), tetramethylthiuram disulfide (TMTD), tetramethylthiuram monosulfide (TMTM), or a combination thereof.

62. The composition of claim 57, wherein the dithiocarbamate comprises zinc dimethyldithiocarbamate (ZDMC), zinc diethyldithiocarbamate (ZDEC), zinc dibutyldithiocarbamate (ZDBC), nickel dibutyldithiocarbamate (NDBC), sodium dibenzyldithiocarbamate (SBEC), sodium diethyldithiocarbamate (SDEC), tellurium diethyldithiocarbamate (TDEC), zinc dibenzyldithiocarbamate (ZEBC), or a combination thereof.

63. The composition of any one of claims 46-62, wherein the one or more rubber chemicals comprise one or more activators.

64. The composition of claim 63, wherein the one or more activators comprise a metal oxide, an acid, a metal complex, or a combination thereof.

65. The composition of claim 64, wherein the metal oxide comprises zinc oxide, magnesium oxide, lead oxide, or a combination thereof.

66. The composition of claim 64, wherein the acid comprises stearic acid, lauric acid, or a combination thereof.

67. The composition of claim 64, wherein the metal complex comprises zinc ethylhexanoate.

68. The composition of any one of claims 46-67, wherein the one or more rubber chemicals comprise one or more pre-vulcanization inhibitors.

69. The composition of claim 68, wherein the one or more pre-vulcanization inhibitors comprise 7V-(cyclohexylthio)phthalimide (CTP), benzoic anhydride, salicylic anhydride, phthalic anhydride, or a combination thereof.

70. The composition of any one of claims 16-69, wherein the composition comprises one or more plasticizers.

71. The composition of claim 70, wherein the composition comprises from about 0.1 wt / wt % to about 10 wt / wt % of the compound and from about 5 wt / wt % to about 95 wt / wt % of one or more plasticizers.

72. The composition of claims 70 or 71, wherein the composition comprises from about 0.1 phr to about 30 phr of one or more plasticizers.

73. The composition of claim 72, wherein the composition comprises from about 1 phr to about 20 phr of one or more plasticizers.

74. The composition of any one of claims 70-73, wherein the one or more plasticizers comprise a mineral oil, an organic ester, a resin, a wax, an ester plasticizer, a naturally derived oil, or a combination thereof.

75. The composition of claim 74, wherein the mineral oil is naphthenic oil, paraffinic oil, or aromatic oil.

76. The composition of claim 74, wherein the naturally derived oil is soybean oil, vegetable oil, or orange oil.

77. The composition of any one of claims 16-76, wherein the composition further comprises one or more additional anti degradants.

78. The composition of claim 77, wherein the composition comprises from about 0.1 wt / wt % to about 10 wt / wt % of the compound and from about 5 wt / wt % to about 95 wt / wt % of the one or more additional anti degradants.

79. The composition of claim 77 or 78, wherein the one or more additional anti degradants are present in an amount of from about 0.001 phr to about 10 phr.

80. The composition of claim 79, wherein the one or more additional anti degradants are present in an amount of from about 0.1 phr to about 5 phr.

81. The composition of claim 80, wherein the one or more additional anti degradants are present in an amount of from about 0.5 phr to about 5 phr.

82. The composition of claim 81 , wherein the one or more additional anti degradants are present in an amount of from about 1 phr to about 5 phr.

83. The composition of any one of claims 77-82, wherein one additional antidegradant is an antioxidant.

84. The composition of any one of claims 77-82, wherein one additional antidegradant is an antiozonant.

85. The composition of any one of claims 77-84, wherein the one additional antidegradant is a paraphenylenediamine (PPD), a trimethyldihydroquinoline (TMQ), a phenolic, an alkylated diphenylamine (DPA), or a diphenylamine-ketone condensate.

86. The composition of claim 85, wherein the PPD is 7V1-(4-methylpentan-2-yl)-A4-phenylbenzene- 1 ,4-diamine (6PPD), 7V-(1 ,4-dimethyl pentyl )-A"-phenyl -p-phenyl enedi ami ne (7PPD), 7V1-phenyl-A4-(propan-2-yl)benzene-l,4-diamine (IPPD), N , / V-di -scc-butyl -p-phenylenediamine (44PD), A,A-bis(l,3-dimethylbutyl)-p-phenylenediamine (66PD), N,N'~ bis(l,4-dimethylpentyl)-p-phenylenediamine (77PD), or A-A-dioctyl- / ?-phenylenediamine (88PD).

87. The composition of claim 86, wherein the PPD is 6PPD.

88. The composition of claim 86, wherein the TMQ is 2,2,4-trimethyl-l,2-dihydroquinoline or an oligomer or polymer thereof.

89. A composition comprising the compound of any one of claims 1-16 and one or more carriers.

90. A composition comprising any one or more of the compounds of Table 3, or a salt or solvate thereof, and one or more carriers.

91. A process for preparing the composition of claim 89 or 90, the process comprising admixing the compound and the one or more carriers.

92. A vulcanized elastomeric article comprising the compound of any one of claims 1-16.

93. A vulcanized elastomeric article comprising any one or more of the compounds of Table 3, or a salt or solvate thereof.

94. A vulcanized elastomeric article prepared using the composition of any one of claims 19-88.

95. The vulcanized elastomeric article of any one of claims 92-94, wherein the vulcanized elastomeric article is a tire.

96. The vulcanized elastomeric article of claim 95, wherein the tire is a passenger vehicle tire, a light truck tire, a heavy truck or bus tire, a motorcycle tire, an agriculture tire, an earthmover tire, an airplane tire, or a racing tire.

97. The vulcanized elastomeric article of any one of claims 92-94, wherein the vulcanized elastomeric article is a component of a tire.

98. The vulcanized elastomeric article of claim 97, wherein the component is a bead, a belt, a body ply, an inner liner, a sidewall, an undertread, or a tread.

99. The vulcanized elastomeric article of any one of claims 92-94, wherein the vulcanized elastomeric article is a rubber overshoe, a sealing strip, an acoustic panel, an air spring, a bellow, a membrane, a tactile sensor, a crash pad, a hose, a conveyor belt, or a flooring.

100. A process for preparing a vulcanized elastomeric article, the process comprising: (a) forming the composition of any one of claims 19-88 into a formed shape; and (b) vulcanizing the formed shapeto provide a vulcanized elastomeric article.

101. The process of claim 100, wherein the vulcanizing is performed at an average temperature of from about 120 °C to about 180 °C.

102. The process of claim 101, wherein the vulcanizing is performed at an average temperature of from about 140 °C to about 160 °C.

103. The process of any one of claims 100-102, wherein the vulcanized elastomeric article is a tire.

104. The process of claim 103, wherein the tire is a passenger vehicle tire, a light truck tire, a heavy truck or bus tire, a motorcycle tire, an agriculture tire, an earthmover tire, an airplane tire, or a racing tire.

105. The process of any one of claims 100-102, wherein the vulcanized elastomeric article is a component of a tire.

106. The process of claim 105, wherein the component is a bead, a belt, a body ply, an inner liner, a sidewall, an undertread, or a tread.

107. The process of any one of claims 100-102, wherein the vulcanized elastomeric article is a rubber overshoe, a sealing strip, an acoustic panel, an air spring, a bellow, a membrane, a tactile sensor, a crash pad, a hose, a conveyor belt, or a flooring.

108. A lubricant composition comprising a lubricant and the compound of any one of claims 1-16.

109. A lubricant composition comprising a lubricant and any one or more of the compounds of Table 3, or a salt or solvate thereof.

110. A combustible fuel composition comprising a combustible fuel and the compound of any one of claims 1-16.

111. A combustible fuel composition comprising a combustible fuel and any one or more of the compounds of Table 3, or a salt or solvate thereof112. A fuel additive composition comprising a fuel additive and the compound of any one of claims 1-16.

113. A fuel additive composition comprising a fuel additive and any one or more of the compounds of Table 3, or a salt or solvate thereof114. A process for retreading tires, the process comprising:(a) applying the composition of any one of claims 19-88 to a tire;(b) disposing a pre-vulcanized tread around the tire;(c) disposing a curing envelope around the tire; and(d) vulcanizing the tire.

115. A kit comprising the composition of any one of claims 16-88 and instructions for using the composition in a vulcanizable elastomeric composition.

116. A kit comprising the composition of any one of claims 19-88 and instructions for using the composition to prepare a vulcanized elastomeric article.

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