Heteroaryl antidegradants

Abstract

The present disclosure provides compounds represented by Formula (I): or salts or solvates thereof, wherein R1, R2, R3, R4, X1, X2, and X3 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

HETEROARYL ANTIDEGRADANTSBACKGROUNDField

[0001] The present disclosure provides compounds with antidegradant, 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

[0002] 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.

[0003] 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 from environmental 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 themechanical 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.

[0004] 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 long-term resistance to fatigue and crack propagation over the known antioxidants discussed immediately below.

[0005] 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. There exists a need for new compounds and compositions having antidegradant properties for use in tires and other rubber articles.BRIEF SUMMARY

[0006] 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 any one of Formulae (I)-(VII) below, collectively referred to herein as "Compounds of the Disclosure" or individually as a "Compound of the Disclosure."

[0007] 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 antidegradants; 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, collectively referred to herein as "Compositions of the Disclosure" or individually as a "Composition of the Disclosure."

[0008] The present disclosure also provides Compositions of the Disclosure comprising a Compound of the Disclosure and one or more elastomers.

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

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

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

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

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

[0014] 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.

[0015] The present disclosure also provides vulcanized elastomeric articles comprising a Compound of the Disclosure.

[0016] 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.

[0017] 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 shape to provide a vulcanized elastomeric article.

[0018] The present disclosure also provides lubricant compositions comprising a lubricant and a Compound of the Disclosure.

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

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

[0021] 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.

[0022] The present disclosure also provides kits comprising a composition described herein and instructions for using the composition in a vulcanizable elastomeric composition.

[0023] The present disclosure also provides kits comprising a composition described herein and instructions for using the composition to prepare a vulcanized elastomeric article.

[0024] 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.

[0025] 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.BRIEF DESCRIPTION OF THE DRAWINGS

[0026] Fig. l is a line graph depicting aJH nuclear magnetic resonance (NMR) spectrum of Compound 1 in ^ / -chloroform (CDCh).

[0027] Fig. 2 is a line graph depicting a13C NMR spectrum of Compound 1 in ^ / -chloroform (CDCh).

[0028] Fig. 3 is a liquid chromatography (LC) chromatogram of Compound 1.DETAILED DESCRIPTION

[0029] In one embodiment, Compounds of the Disclosure are compounds having Formula (I):or a salt, solvate, or stereoisomer thereof, wherein:

[0030] X1, X2, and X3are each independently selected from the group consisting of -CR- and -N-;

[0031] R is at each occurrence independently selected from the group consisting of hydrogen, C1-C9 alkyl, C1-C9 alkoxy, and C1-C9 alkylthio;

[0032] R1is selected from the group consisting of C1-C12 alkyl, -CHRlaRlb, C3-C6 cycloalkyl, optionally substituted phenyl, and optionally substituted 5- or 6- membered heteroaryl;

[0033] Rlais selected from the group consisting of optionally substituted phenyl, C3-C6 cycloalkyl, and optionally substituted 5- or 6-membered heteroaryl;

[0034] Rlbis independently selected from the group consisting of hydrogen and Ci-Ce alkyl;

[0035] R2is selected from the group consisting of C1-C12 alkyl, -CHR2aR2b, C3-C6 cycloalkyl, optionally substituted phenyl, and optionally substituted 5- or 6- membered heteroaryl;

[0036] R2ais selected from the group consisting of optionally substituted phenyl, C3-C6 cycloalkyl, and optionally substituted 5- or 6-membered heteroaryl;

[0037] R2bis independently selected from the group consisting of hydrogen and Ci-Ce alkyl; and

[0038] R3and R4are each independently selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, and tert-butyl.

[0039] In another embodiment, Compounds of the Disclosure are compounds having Formula (I), with provisos that:

[0040] (i) if R1and R3are both methyl, both n-propyl, or both iso-propyl, R2is not optionally substituted phenyl, or

[0041] (ii) if R2and R4are both methyl, both n-propyl, or both iso-propyl, R1is not optionally substituted phenyl, or

[0042] (iii) if X1and X2are -CH-, X3is -N-, R1is iso-propyl, and R3and R4are hydrogen, R2is not phenyl, or

[0043] (iv) if X1and X2are -CH-, X3is -N-, R1is 4-(dimethylamino)phenyl, and R3and R4are hydrogen, R2is not 4-(dimethylamino)phenyl.

[0044] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein R3and R4are independently selected from the group consisting of hydrogen and methyl.

[0045] In another embodiment, Compounds of the Disclosure are compounds having Formula (II):wherein R1, R2, R3, and R4are as defined in connection with Formula (I), with provisos that (i) if R1and R3are both methyl, both n-propyl, or both iso-propyl, R2is not optionally substituted phenyl; or (ii) if R2and R4are both methyl, both n-propyl, or both iso-propyl, R1is not optionally substituted phenyl.

[0046] In another embodiment, Compounds of the Disclosure are compounds having Formula (III):(Ill), wherein R1, R2, R3, and R4are as defined in connection with Formula (I), with provisos that (i) if R1and R3are both methyl, both n-propyl, or both iso-propyl, R2is not optionally substituted phenyl; or (ii) if R2and R4are both methyl, both n-propyl, or both iso-propyl, R1is not optionally substituted phenyl (iii) if R1is iso-propyl, and R3and R4are hydrogen, R2is not phenyl, or (iv) if R1is 4-(dimethylamino)phenyl, and R3and R4are hydrogen, R2is not 4-(dimethylamino)phenyl.

[0047] In another embodiment, Compounds of the Disclosure are compounds havingFormula (IV):wherein R1, R2, R3, and R4are as defined in connection with Formula (I), with provisos that (i) if R1and R3are both methyl, both n-propyl, or both iso-propyl, R2is not optionally substituted phenyl; or (ii) if R2and R4are both methyl, both n-propyl, or both iso-propyl, R1is not optionally substituted phenyl.

[0048] In another embodiment, Compounds of the Disclosure are compounds having Formula (V):wherein R1, R2, R3, and R4are as defined in connection with Formula (I), with provisos that (i) if R1and R3are both methyl, both n-propyl, or both iso-propyl, R2is not optionally substituted phenyl; or (ii) if R2and R4are both methyl, both n-propyl, or both iso-propyl, R1is not optionally substituted phenyl.

[0049] In another embodiment, Compounds of the Disclosure are compounds having Formula (VI):wherein R1, R2, R3, and R4are as defined in connection with Formula (I), with provisos that (i) if R1and R3are both methyl, both n-propyl, or both iso-propyl, R2is not optionally substituted phenyl; or (ii) if R2and R4are both methyl, both n-propyl, or both iso-propyl, R1is not optionally substituted phenyl.

[0050] In another embodiment, Compounds of the Disclosure are compounds havingFormula (VII):wherein R1, R2, R3, and R4are as defined in connection with Formula (I) with provisos that (i) if R1and R3are both methyl, both n-propyl, or both iso-propyl, R2is not optionally substituted phenyl; or (ii) if R2and R4are both methyl, both n-propyl, or both iso-propyl, R1is not optionally substituted phenyl.

[0051] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(VII), wherein R3is hydrogen.

[0052] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(VII), wherein R4is hydrogen.

[0053] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(VII), wherein R3and R4are hydrogen.

[0054] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(VII), wherein R1is C1-C12 alkyl.

[0055] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(VII), wherein R1is methyl, ethyl, propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, or nonyl.

[0056] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(VII), wherein R1is iso-propyl.

[0057] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(VII), wherein R1is:

[0058] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(VII), wherein R1is optionally substituted phenyl.

[0059] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(VII), wherein R1is -CHRlaRlb.

[0060] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(VII), wherein:

[0061] Rlais selected from the group consisting of:

[0062] Q1is -NH-, -O-, or -S-; and

[0063] Rlbis hydrogen.

[0064] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(VII), wherein Q1is -O-.

[0065] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(VII), wherein R2is C1-C12 alkyl.

[0066] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(VII), wherein R2is methyl, ethyl, propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, or nonyl.

[0067] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(VII), wherein R2is iso-propyl.

[0068] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(VII), wherein R2is:

[0069] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(VII), wherein R2is optionally substituted phenyl.

[0070] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(VII), wherein R2is -CHR2aR2b.

[0071] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(VII), wherein:

[0072] R2ais selected from the group consisting of:

[0073] Q2is -NH-, -O-, or -S-; and

[0074] R2bis hydrogen.

[0075] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(VII), wherein Q2is -O-.

[0076] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(VII), wherein R1and R2are the same.

[0077] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(VII), wherein R1and R2are not the same.

[0078] 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

[0079] Compounds of the Disclosure can be useful as anti degradants, e.g., antiozonants and / or antioxidants, as additives in lubricants, and as additives in combustible fuels.

[0080] Compounds of the Disclosure can be prepared, for example, by reacting a diaminoheteroarene with a ketone, as shown in Scheme 1, wherein Rlcis, for example, C1-C12 alkyl, C3-C6 cycloalkyl, optionally substituted phenyl, or optionally substituted 5- or 6-membered heteroaryl, and Rldis, for example, hydrogen or Ci-Ce alkyl.Scheme 1y

[0081] Compounds of the Disclosure can also be prepared, for example, starting from an appropriate dinitro- or nitroamino-heteroarene, as shown in Scheme 2.Scheme 2yZ = NO2or NH2Definitions

[0082] 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 straight-chain 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. Nonlimiting exemplary C1-C12 alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, ec-butyl, / e / 7-butyl, zso-butyl, 3pentyl, hexyl, heptyl, octyl, nonyl, and decyl.

[0083] 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, wheren 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-Ce alkyl.

[0084] The term "halo" or "halogen" as used herein by itself or as part of another group refers to -Cl, -F, -Br, or -I.

[0085] The term "nitro" as used herein by itself or as part of another group refers to -NO2.

[0086] The term "cyano" as used herein by itself or as part of another group refers to -CN.

[0087] The term "hydroxy" as herein used by itself or as part of another group refers to -OH.

[0088] 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.

[0089] In one embodiment, the amino is -NH2.

[0090] 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.

[0091] 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)2and -N(CH3)CH2CH(CH3)2.

[0092] 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.

[0093] 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 C2alkyl. Non-limiting exemplary haloalkyl groups include fluorom ethyl, difluorom ethyl, trifluoromethyl, pentafluoroethyl, 1,1-difluoroethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, 4,4,4-trifluorobutyl, and trichloromethyl groups.

[0094] 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 tertbutoxy.

[0095] 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.

[0096] 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-Ci2cycloalkyl, or the number of carbons designated, e.g., a C3-Ce cycloalkyl such a cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. In one embodiment, thecycloalkyl 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, norbomyl, decalin, adamantyl, cyclohexenyl, and spiro[3.3]heptane.

[0097] 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.

[0098] The term "heterocyclo" 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.

[0099] The term "optionally substituted heterocyclo" 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, wheren the substituents are each independently halo, nitro,cyano, hydroxyl, amino, (e.g., -NH2, alkylamino, or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl, or cycloalkyl.

[0100] 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., 1H- pyrrol-2-yl and lH-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, pyridin-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.

[0101] 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.

[0102] 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 includes enantiomers and isomers of compounds with more than one chiral center that are not mirror images of one another (diastereomers).

[0103] The term "chiral center" or "asymmetric carbon atom" refers to a carbon atom to which four different groups are attached.

[0104] 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.

[0105] The term "racemic" refers to a mixture of equal parts of enantiomers and which mixture is optically inactive.

[0106] 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.

[0107] The stereochemical terms and conventions used in the specification are meant to be consistent with those described in wre & Appl. Chem 65:2193 (1996), unless otherwise indicated.

[0108] 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]obs is 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.

[0109] 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.

[0110] Salts and solvates, e.g., hydrates, of the Compounds of the Disclosure can also be used in the methods disclosed herein.[OHl] 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 addition salts 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, digluconate, 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 quaternized 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.

[0112] 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.

[0113] 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 el al. J. Pharmaceut. Sci., 93(3 / 601-611 (2004), whichdescribes 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 Tender et al., AAPS Pharm. Sei. 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.

[0114] 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.

[0115] 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).

[0116] 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.

[0117] 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 = 0.50 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 %).

[0118] 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.

[0119] 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 antidegradant, 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 anti degradant, or acombination thereof. 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 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.

[0120] 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

[0121] 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 antidegradants; 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.

[0122] In some embodiments, the composition comprises from about 0.1 wt / wt% to about10 wt / wt% of the Compound of the Disclosure, e.g., 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% to about 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 9wt / 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 5 wt / 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.

[0123] In some embodiments, a Composition of the Disclosure comprises from about15 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 %, fromabout 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.

[0124] 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.

[0125] In another embodiment, a Composition of the Disclosure comprises a Compound of the Disclosure and one or more elastomers.

[0126] 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 (IIR), 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), poly chloromethyloxiran (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.

[0127] 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).

[0128] 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.

[0129] In some embodiments, a Composition of the Disclosure comprises from about 15 wt / wt % to about 85 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 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 one or more elastomers.

[0130] 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 %, or about 95 wt / wt % of one or more elastomers.

[0131] 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.

[0132] 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.

[0133] In some embodiments, a Composition of the Disclosure comprises about 3 phr of a Compound of the Disclosure. In some embodiments, the composition comprises about0.01 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.

[0134] In some embodiments, a Composition of the Disclosure comprises a Compound of the Disclosure and one or more fillers.

[0135] 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.

[0136] In some embodiments, the filler is derived from natural sources. For example, silica may be derived from rice husks.

[0137] In some embodiments, a Composition of the Disclosure comprises from about15 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.

[0138] 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.

[0139] 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, fromabout 150 phr to about 500 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.

[0140] 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.

[0141] 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.

[0142] 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.

[0143] 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.

[0144] 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 N- / ert-butyl-2-benzothi azole sulfenimide (TBSI). Non-limiting examples of sulfenamides include N- / c / 7-butyl-2- benzothiazylsulfenamide (TBBS), 7V-cyclohexylbenzothiazol-2-sulfenamide (CBS), dicyclohexyl-2-benzothiazolesulfenamide (DCBS), N-oxy di ethylene benzothiazole sulfenamide (OBTS), N-oxy di ethylenethiocarbamyl-N'-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 dibutyl di thiocarbamate (ZDBC), nickel dibutyl dithiocarbamate (NDBC), sodium dibenzyldithiocarbamate (SBEC), sodium diethyldithiocarbamate (SDEC), tellurium diethyldithiocarbamate (TDEC), and zinc dibenzyldithiocarbamate (ZEBC).

[0145] 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.

[0146] 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 7V- (cyclohexylthio)phthalimide (CTP), benzoic anhydride, salicylic anhydride, and phthalic anhydride.

[0147] In some embodiments, a Composition of the Disclosure comprises from about15 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.

[0148] 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.

[0149] 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, 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 rubber chemicals.

[0150] 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.

[0151] 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.

[0152] In some embodiments, a Composition of the Disclosure comprises from about15 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.

[0153] 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.

[0154] 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 toabout 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, 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.

[0155] 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.

[0156] In some embodiments, a Composition of the Disclosure further comprises one or more additional anti degradants that is not a Compound of the Disclosure. In some embodiments, the one or more additional anti degradants is an antioxidant. In some embodiments, the one or more additional anti degradants is an antiozonant. Non-limiting examples of anti degradants include paraphenylenediamines (PPDs), trimethyldihydroquinolines (TMQs), phenolics, alkylated diphenylamines (DP As), diphenylamineketone condensates, and natural anti degradants. Non-limiting examples of PPDs include N1-(4-methyl pentan-2-yl )-N4-phenylbenzene- 1 ,4-diamine (6PPD), N-( 1 ,4- dimethylpentyl)-N'-phenyl-p-phenylenediamine (7PPD), 7V1-phenyl-A4-(propan-2- yl)benzene-l,4-diamine (IPPD), A( '-di -scc-butyl - -phenylenedi amine (44PD), N,N'~ bis(l,3-dimethylbutyl)-p-phenylenediamine (66PD), 7V,A-bis(l,4-dimethylpentyl)-p- phenylenediamine (77PD), and N-N'-dioctyl- -phenylenediamine (88PD). Non-limiting examples of TMQs include 2,2,4-trimethyl-l,2-dihydroquinoline and oligomers or polymers thereof.

[0157] 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.

[0158] 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.

[0159] 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 phrto about 7.5 phr, 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.

[0160] 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.

[0161] 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.

[0162] 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 %, 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 carriers.

[0163] 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.

[0164] 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.

[0165] 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.

[0166] The present disclosure also provides combustible fuel compositions comprising a combustible fuel and a Compound of the Disclosure. Non-limiting examples ofcombustible fuel include gasoline, diesel, kerosene, liquefied petroleum gas, synthetic fuel, and biodisesel.

[0167] 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.

[0168] In some embodiments, the present disclosure provides a composition recited in Table 2.Table 2

[0169] In some embodiments, the vulcanized tire or other rubber article composition of Table 2 comprises 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 vulcanized tire or other rubber article of Table 2 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.

[0170] In some embodiments, the unvulcanized in-tire component or built up component or other end use component composition of Table 2 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 2 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

[0171] 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.

[0172] The present disclosure also provides vulcanized elastomeric articles prepared using a composition described herein.

[0173] 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.

[0174] 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.

[0175] 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.Processes

[0176] 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.

[0177] 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.

[0178] In some embodiments, the vulcanizing is performed at an average temperature of about 150 °C. In some embodiments, the vulcanizing is performed at an averagetemperature of about 80 °C, about 100 °C, about 120 °C, about 140 °C, about 160 °C, about 180 °C, or about 200 °C.

[0179] The present disclosure alsp 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

[0180] 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 N2,N5-bis(5-methylhexan-2-yl)pyridine-2,5-diamine (Compound 1)

[0181] To a 300-mL Parr autoclave was loaded pyridine-2,5-diamine (0.605 g; 5.54 mmol), toluene (130 mL), 3% Pt / C sulfided (Johnson Matthey; 9-10 mg wet), and methyl isoamyl ketone (MIAK) (3.8 mL; 27.1 mmol). The reaction mixture was heated to 245 °C. Once the temperature was reached, the autoclave was continuously fed with EE (set pressure = 500 PSIG) for several hours. The reaction mixture was allowed to stand at room temperature under N2 protection overnight. At that stage, approx. 60%monoalkylated intermediates and 8-9% desired dialkylated product had formed (percentage areas as measured by LC-UV analysis at 260 nm detection). The reaction mixture was heated to 250 °C. Once the temperature was reached, the autoclave was continuously fed with H2 (set pressure = 700 PSIG) for approx. 20 hours. Upon cooling to room temperature, the mixture post reaction was filtered through Celite S. The clave was rinsed with ethyl acetate (120 mL) and the mixture was filtered through the Celite S bed. The combined filtrates were stripped of their volatiles under reduced pressure (rotary evaporator; water bath = 60 °C). The obtained black liquid was loaded into a 1 " inner diameter column previously prepared with silica gel 60 and 50% ethyl acetate in hexanes (height of silica = 6.25"). The column was eluted with 50% ethyl acetate in hexanes. Each portion was analyzed by TLC (50% ethyl acetate in hexanes). The portions having Rf = 0.6 were collected, combined, and stripped of volatiles under reduced pressure (rotary evaporator; water bath = 55 °C) to afford 0.216 g of N2,N5-bis(5- methylhexan-2-yl)pyridine-2,5-diamine (Compound 1) as a dark-red oil. Compound 1 was characterized byJH and13C nuclear magnetic resonance (NMR) spectroscopy, as shown in Figs. 1 and 2, respectively. LC-UV analysis showed 97.7% purity at 260 nm detection, as shown in Fig. 3. Mass (m / z): 306.3 [M+l]+.EXAMPLE 2Synthesis of N2,N5-bis(5-methylhexan-2-yl)pyrimidine-2,5-diamine (Compound 83)

[0182] To a stirred solution of pyrimidine-2,5-diamine (70.0 g, 0.635 mol) in di chloroethane (2800 mL) was added methyl isoamyl ketone (MIAK) (537 mL, 3.81 mol) and NaOAc (182 g, 2.22 mol), stirred for 10 min. Cooled to 20-25 °C and added sodium triacetoxyborohydride (STAB) (808 g, 3.81 mol) as portion wise, maintained for 16 hr at RT. After completion of the reaction, (monitored by TLC), reaction mixture quenched with Sat. NaHCCh solution. Separated organic layer and Aq. layer extracted with DCM (2 x 250 mL). Combined organic layers and dried over sodium sulphate and evaporated under reduced pressure to afford 110.0 g of crude Compound 83.

[0183] The obtained crude compound was purified by column chromatography using silica gel (60-120 mesh) as the stationary phase, eluting with 5-10% ethyl acetate in hexane. Collected the pure fractions and evaporated under vacuum to afford 44.0 g of desired Compound 83 as a pale-yellow solid (>99% purity by HPLC 260 nm, Mass (m / z): 307.24 [M+l]+).

[0184] 'HNMR (400 MHz, DMSO ): 5 7.77 (s, 2H), 5.90 (d, J=8.4 Hz, 1H), 4.50 (d, .7=9,2 Hz, 1H), 3.75-3.74 (m, 1H),3.32 (m, 1H), 1.50-1.49 (m, 4H), 1.47-1.32 (m, 2H), 1.29-1.14 (m, 4H), 1.04 (t, J=7.2 Hz, 6H), 0.86-0.82 (m, 12H)

[0185] 13C NMR (100 MHz, DMSO ): 5 156.61, 144.59, 134.23, 49.36, 46.78, 40.63,40.62, 40.42, 40.21, 40.00, 39.79, 39.58, 39.37, 35.58, 35.27, 34.58, 34.49, 28.11, 28.01, 23.04, 22.98, 21.28, 20.71EXAMPLE 3Synthesis of N2,N5-bis(5-methylhexan-2-yl)pyrazine-2,5-diamine (Compound 84)

[0186] To a stirred solution of 5-bromopyrazin-2-amine (100 g, 0.57 mol) in DMSO (1000 mL) degassed for 10 min and added Cui (21.89 g, 0.11 mol), L-proline (26.47 g, 0.22 mol), and K2CO3 (118.96 g, 0.86 mol) stirred for 10 min, and degassed, then added NH4OH (200 mL, 2 Vol). Heated to 80 °C and maintained for 16 hr at RT. After completion of the reaction, (monitored by TLC), reaction mixture cooled and diluted with methanol (500 mL). Filtered through celite pad, washed with methanol (200 mL), combined organic layers and dried over sodium sulphate and evaporated under reduced pressure to afford 63.5 g of crude Intermediate 84-1. Used in the next step without purification.Step 2

[0187] To a stirred solution of Intermediate 84-1 (63.5 g, 0.57 mol) in EDC (2500 mL) was added MIAK (487 mL, 3.45 mol) and NaOAc (165.5 g, 2.01 mol), stirred for 10 min. Cooled to 20-25 °C and added STAB (611 g, 2.88 mol) as portion wise, maintained for 16 hr at RT. After completion of the reaction, (monitored by TLC), reaction mixture quenched with Sat. NaHCCh solution. Separated organic layer and Aq. layer extracted with DCM (2 x 250 mL). Combined organic layers and dried over sodium sulphate and evaporated under reduced pressure to afford 80.0 g of crude Compound 84. The obtained crude compound was purified by column chromatography using silica gel (60-120 mesh) as the stationary phase, eluting with 5-10% ethyl acetate in hexane. Collected the pure fractions and evaporated under vacuum to afford 42.0 g of desired Compound 84 as a yellow solid (>97% pure by HPLC 260 nm, Mass (m / z): 307.28 [M+H]+).

[0188] 'H NMR (400 MHz, DMSO-77): 5 7.41 (s, 2H), 5.42 (d, 7=8.4 Hz, 2H), 3.66- 3.56(m, 2H), 3 1.51-1.42 (m, 4H), 1.39-1.30 (m, 2H), 1.26-1.11 (m, 4H), 1.06 (t, 7=16 Hz, 6H), 0.84 (d, J= 6.4 Hz, 12 H)

[0189] 13C NMR (100 MHz, DMSO-77): 5 127.97, 46.90, 40.39, 40.19, 39.98, 39.77,39.56, 35.44, 34.69, 28.07, 23.04, 21.22EXAMPLE 4Synthesis of N2-(4-methylpentan-2-yl)-N5-phenylpyrazine-2,5-diamine (Compound 16)Step 1

[0190] To a stirred solution of 5-bromopyrazin-2-amine (40.0 g, 0.229 mol) in methyl isobutylketone (MIBK) (400 mL) was added acetic acid (400 mL) at RT, followed by the addition of NaCNBHs (71.3 g, 1.14 mol), portion wise for 30 min. Stirred the reaction for 16 h at RT. After completion of reaction (monitored by TLC), quenched the reaction with ice-cold water and extracted with ethyl acetate (2 x 400 mL). The combined organic layers were dried over sodium sulphate, filtered and evaporated under vacuum to afford 81 g of crude Intermediate 16-1. The crude compound was purified by silica gel column chromatography (100-200 mesh) eluting with 7-10% ethyl acetate in hexane to afford Intermediate 16-1 as a pale-yellow gummy liquid (>98% pure by HPLC 260 nm).Step 2

[0191] Purged nitrogen into 1,4-Dioxane (825 mL) for 30 min, followed by the addition of Pd(OAc)2 (4.82 g, 0.02 mol) and BINAP (39.9 g, 0.06 mol). After purging the reaction mixture with nitrogen for 15-20 min, Intermediate 16-1 (55.0 g, 0.21 mol) and aniline (21.9 g, 0.23 mol) were added followed by the addition of KOtBu (36.0 g, 0.32 mol). Heated the reaction to 85-90°C and maintained for 16 h. After completion of reaction (monitored by TLC), the reaction mixture was cooled to RT and filtered through a celite pad. The filter cake was thoroughly washed with 1,4-Dioxane and the filtrate was evaporated under reduced pressure to get crude residue (110 g). The obtained residue was further purified by silica-gel (100-200 mesh) column chromato graphy eluting with 10- 15% ethyl acetate in hexane to afford 44.0 g of Compound 16 as a pale-yellow solid (>99% pure by HPLC 260 nm, Mass (m / z): 271.14 [M+H]+)

[0192] 1H NMR (400 MHz, DMSO ): 5 8.48 (s, 1H), 7.76 (s, 1H), 7.60 (s, 1H), 7.34 (d,J= 8.4 Hz, 2H), 7.17 (t, J= 8.4 Hz, 2H), 6.74 (t, J= 7.2 Hz, 1H), 6.07 (d, J= 8.4 Hz, 1H),3.91-3.84 (m, 1H), 1.74-1.64 (m, 1H), 1.47-1.41 (m, 2H), 1.26-1.19 (m, 1H), 1.07 (d, J= 864 Hz, 3H), 0.91-0.86 (m, 6H)

[0193] 13C NMR (100 MHz, DMSO-t / e): 5 150.28, 143.75, 143.33, 131.34, 129.13,127.99, 119.17, 116.11, 46.43, 44.39, 25.03, 23.21, 22.98, 21.67EXAMPLE 5Synthesis of 3-methyl-N5-(4-methylpentan-2-yl)-N2-phenylpyrazine-2,5-diamine(Compound 58)

[0194] To a stirred solution of 6-methylpyrazin-2-amine (100.0 g, 0.916 mol) in DMSO (2.0 L) and water (200 mL) was added N-bromosuccinimide (NBS) (179.4 g, 1.00 mol) portion wise at 0-5°C. Warmed the reaction to RT and stirred for 5 h. After completion of reaction (monitored by TLC), quenched the reaction with sat NaHCCh solution and extracted with ethyl acetate (2.0 L). The organic layer was separated and washed with brine (1.0 L). Separated the organic layer, dried over sodium sulphate, filtered and evaporated under vacuum to afford 190 g of crude Intermediate 1 which was purified by silica gel column chromatography (100-200 mesh) eluting with 25-30% ethyl acetate in hexane to afford 125 g of Intermediate 58-1 as an off-white solid.Step 258-1

[0195] To a stirred solution of Intermediate 58-1 (100.0 g, 0.537 mol) in AcOH (1.0 L) was added MIBK (1.0 L) at RT, followed by the addition of NaBHsCN (166.0 g, 2.688 mol) portion wise for 30 min. Stirred the reaction for 16 h at RT. After completion of reaction (monitored by TLC), quenched the reaction with ice-cold water and extracted with ethyl acetate (2 x 1.0 L). The combined organic layers were dried over sodium sulphate, filtered and evaporated under vacuum to afford 190 g of crude Intermediate 58- 2. The crude material was purified by silica gel column chromatography (100-200 mesh) eluting with 10-15% ethyl acetate in hexane to afford 120.0 g Intermediate 58-2 as a brown gummy liquid.Step 3

[0196] Purged nitrogen into 1,4-Dioxane (900 mL) for 30 min, followed by the addition of Pd2dba3 (20.2 g, 0.022 mol) and X-Phos (31.6 g, 0.066 mol). After purging the reaction mixture with nitrogen for 15-20 min, Intermediate 58-2 (60.0 g, 0.221 mol) and aniline (22.2 mL, 0.243 mol) were added followed by the addition of KOtBu (37.1 g, 0.331 mol). Heated the reaction to 85-90°C and maintained for 16 h. After completion of reaction (monitored by TLC), the reaction mixture was cooled to RT and filtered through a celite pad. The filter cake was thoroughly washed with 1,4-Dioxane and the filtrate was evaporated under reduced pressure to get crude residue (110 g). The obtained residue was further purified by silica-gel (100-200 mesh) column chromatography eluting with 4-6% ethyl acetate in hexane to afford 45 g of Compound 58 as pale yellow solid (>97% pure by HPLC 260 nm, Mass (m / z): 285.09 [M+H]+).

[0197] XH NMR (400 MHz, DMSO-t / e): 5 7.58 (s, 1H), 7.48 (s, 1H), 7.15-7.11 (m, 2H), 7.07-7.04 (m, 2H), 6.69 (t, J= 7.2 Hz, 1H), 6.15 (d, J= 8.4 Hz, 1H), 6.48 (d, J= 7.6 Hz, 2H), 3.93-3.89 (m, 1H), 2.29 (s, 3H), 1.70-1.64 (m, 1H), 1.48-1.42 (m, 1H), 1.26-1.19 (m, 1H), 1.09 (d, J= 6.4 Hz, 3H), 0.89 (d, J= 6.4 Hz, 3H), 0.87 (d, J= 6.8 Hz, 3H)

[0198] 13C NMR (100 MHz, DMSO ): 5 150.87, 144.98, 141.82, 139.62, 128.95,125.83, 118.66, 116.05, 46.55, 44.27, 25.06, 23.27, 23.00, 21.68, 20.94EXAMPLE 6Synthesis of 3-methyl-N2-(4-methylpentan-2-yl)-N5-phenylpyrazine-2,5-diamine (Compound 59)

[0199] To a stirred solution of 3-methylpyrazin-2-amine (100.0 g, 0.916 mol) in DMSO (2.0 L) and water (200 mL) was added NBS (179.4 g, 1.00 mol) portion wise at 0-5°C. Warmed the reaction to RT and stirred for 5 h. After completion of reaction (monitored by TLC), quenched the reaction with sat NaHCCh solution and extracted with ethyl acetate (2.0 L). The organic layer was separated and washed with brine (1.0 L). Separated the organic layer, dried over sodium sulphate, filtered and evaporated under vacuum to afford 180 g of crude Intermediate 1 which was purified by silica gel column chromatography (100-200 mesh) eluting with 25-30% ethyl acetate in hexane to afford 140 g of Intermediate 59-1 as an off-white solid.Step 2

[0200] To a stirred solution of Intermediate 59-1 (50.0 g, 0.26 mol) in AcOH (500 mL) was added MIBK (500 mL) at RT, followed by the addition of NaBHsCN (83.3 g, 1.34 mol) portion wise for 30 min. Stirred the reaction for 16 h at RT. After completion of reaction (monitored by TLC), quenched the reaction with ice-cold water and extracted with ethyl acetate (2 x 500 mL). The combined the organic layers were dried over sodium sulphate, filtered and evaporated under vacuum to afford 90 g of crude compound. The crude compound was purified by silica gel column chromatography (100-200 mesh) eluting with hexane to afford 40 g of Intermediate 59-2 as a brown gummy liquid.Step 3

[0201] Purged nitrogen into 1,4-Dioxane (900 mL) for 30 min, followed by the addition of Pd2dba3 (19.8 g, 0.022 mol) and X-Phos (30.6 g, 0.066 mol). After purging the reaction mixture with nitrogen for 15-20 min, Intermediate 59-2 (60.0 g, 0.221 mol) and aniline (22.2 mL, 0.243 mol) were added followed by the addition of KOtBu (36.0 g, 0.332 mol). Heated the reaction to 85-90°C and maintained for 16 h. After completion of reaction (monitored by TLC), the reaction mixture was cooled to RT and filtered through a celite pad. The filter cake was thoroughly washed with 1,4-Dioxane and the filtrate was evaporated under reduced pressure to get crude residue (110 g). The obtained residue was further purified by silica-gel (100-200 mesh) column chromatography eluting with 4-6% ethyl acetate in hexane to afford 48 g of Compound 59 as brown gummy. Triturated the residue in n-pentane to obtain solid, which was filtered and dried under vacuum to afford29.0 g of Compound 59 as yellow solid (>99% pure by HPLC 260 nm, Mass (m / z):285.12 [M+H]+)

[0202] 1H NMR (400 MHz, DMSO ): 5 8.36 (s, 1H), 7.64 (s, 1H), 7.32 (d, J= 7.6 Hz,2H), 7.16 (t, J= 7.6 Hz, 2H), 6.72 (t, J= 7.2 Hz, 1H), 5.30 (d, J= 8.4 Hz, 1H), 4.12-4.03 (m, 1H), 2.27 (s, 3H), 1.72-1.64 (m, 1H), 1.58-1.51 (m, 1H), 1.29-1.23 (m, 1H), 1.10 (d, J= 6.4 Hz, 3H), 0.89 (d, J= 6.4 Hz, 3H), 0.85 (d, J= 6.8 Hz, 3H)

[0203] 13C NMR (100 MHz, DMSO ): 5 147.95, 144.11, 142.23, 136.27, 129.15,128.05, 118.95, 115.93, 46.20, 44.31, 25.12, 23.24, 23.04, 21.70, 20.66EXAMPLE 7Synthesis of 3-methyl-N2,N5-bis(5-methylhexan-2-yl)pyrazine-2,5-diamine (Compound 85)

[0204] To a stirred solution of 5-bromo-3-methylpyrazin-2-amine (100.0 g, 0.534 mol) in DMSO (1.0 L) was added Cui (20.4 g, 0.106 mol) and L-Proline (24.4 g, 0.214) at RT. After purging the reaction mixture with nitrogen for 5-20 min, K2CO3 (109.0 g, 0.802 mol) and 25% aq ammonia (150 mL, 1.87 mol) were added. Heated the reaction to 80- 85°C and stirred for 16 h. After completion of reaction (monitored by TLC), cooled to RT, the solid formed was filtered and washed with 10% MeOH in DCM (500 mL). Evaporated the filtrate under vacuum to afford crude Intermediate 85-1 as black liquid, which was used as such for next reaction considering 66.0 g as 100% yield.Step 2

[0205] To a stirred solution of Intermediate 85-1 (66.0 g, crude, 0.532 mol) in MIAK (660 mL, 10.0 vol) was added acetic acid (660 mL, 10.0 vol) at RT, followed by the addition of NaBHsCN (164.0 g, 2.661 mol) portion wise for 30 min. Stirred the reaction for 16 h at RT. After completion of reaction (monitored by TLC), quenched the reaction with ice-cold water and extracted with ethyl acetate (2 x 1.0 L). The combined organic layers were dried over sodium sulphate, filtered and evaporated under vacuum to afford 180 g of crude compound. The crude compound was purified by silica gel column chromatography (100-200 mesh) eluting with 4-6% ethyl acetate in hexane to afford 140 g of Compound 85 as a brown gummy liquid (contained 5-methylhexan-2-ol). To a solution of the 140 g of Compound 85 in diethyl ether (280 mL) was added 2M HC1 in diethyl ether (420 mL) at 0°C, stirred for 30 min and the obtained solid was filtered. Suspended the solid compound in DCM (500 mL) and sat NaHCCh solution was added until pH~8. Separated the organic layer, dried over sodium sulphate and evaporated under vacuum to afford residue, which was further purified by silica gel column chromatography (100-200 mesh) eluting with 10-15% ethyl acetate in hexane to afford 44.9 g of Compound 85 as a brown gummy liquid (>96% pure by HPLC 260 nm, Mass (m / z): 321.25 [M+H]+)

[0206] 'HNMR (400 MHz, DMSO ): 5 7.25 (s, 1H), 5.22 (d, J= 8.4 Hz, 1H), 4.71 (d, J= 8.4 Hz, 1H), 3.84-3.72 (m, 1H), 3.65-3.55 (m, 1H), 2.16 (s, 3H), 1.53-1.45 (m, 4H), 1.38-1.33 (m, 2H), 1.24-1.12 (m, 4H), 1.07 (d, J= 6.4 Hz, 3H), 1.07 (d, J= 6.4 Hz, 3H), 0.86-0.83 (m, 12H)

[0207] 13C NMR (100 MHz, DMSO-t / e): 5 147.23, 145.67, 136.31, 123.94, 47.04, 46.71,35.70, 35.47, 34.71, 34.65, 28.06, 28.00, 23.10, 23.06, 22.97, 21.29, 21.21, 20.52EXAMPLE 8Synthesis of N2,N5-bis(furan-2-ylmethyl)pyridine-2,5-diamine (Compound 7)

[0208] To a stirred suspension of 2-chloro-5-nitropyridine (100.0 g, 0.630 mol) and furan-2-ylmethanamine (59 mL, 0.630 mol) in water (500 mL) added KF (73 g, 1.25 mol) and then stirred for 10 min. The resulting reaction contents were heated to 100 °C and stirred for 16 hr. After completion of the reaction, (monitored by TLC), reaction mixture quenched with water and extracted with EtOAc (2 x 100 mL), separated organic layer and combined organic layers were dried over sodium sulphate and evaporated under reduced pressure to afford 156.0 g of crude Intermediate 7-1. The obtained crude compound was purified by column chromatography using silica gel (100-200 mesh) as the stationary phase, eluting with 0-30% ethyl acetate in hexane. Collected the pure fractions and evaporated under reduced pressure to afford 120.0 g of desired Intermediate 7-1 as a paleyellow solid.Step 2

[0209] To a stirred solution of Intermediate 7-1 (90.0 g, 0.410 mol) in DCM (900 mL) was added triethyl amine (225 mL, 1.60 mol) and cooled to 0-5 °C. Added Boc anhydride(137 mL, 0.60 mol), followed by DMAP (1.0 g, catalytic) and allowed to stir RT for 16 hr. After completion of the reaction, (monitored by TLC), reaction mixture was quenched with water and extracted with DCM (2 x 250 mL). Combined organic layers and dried over sodium sulphate and evaporated under reduced pressure to afford 123.0 g of crude Intermediate 7-2.Step 3

[0210] To a stirred solution of Intermediate 7-2 (123.0 g, 0.385 mol) in methanol (900 mL) was added furaldehyde (110 mL, 1.155 mol) and 5% Pt / C (61.0 g, 50%w / w) at RT, applied hydrogen pressure (40 bar) and maintained for 16 hr at RT. After completion of the reaction, (monitored by TLC) the reaction mixture was filtered through celite pad, washed with methanol (100 mL). The collected filtrate was evaporated under reduced pressure to afford crude 90.0 g of Intermediate 7-3.

[0211] The obtained crude compound was purified by column chromatography using silica gel (60-120 mesh) as the stationary phase, eluting with 5-10% ethyl acetate in hexane. Collected the pure fractions and evaporated under vacuum to afford 80.0 g of Intermediate 7-3 as a pale-yellow liquid.Step 4

[0212] To a stirred suspension of Intermediate 7-3 (80.0 g, 0.635 mol) in diethyl ether (800 mL) was added diethyl ether- HC1 (800 mL) at 0 °C for about 30-40 min. Reaction mixture allowed to RT and maintained for 16 hr at RT. After completion of the reaction, (monitored by TLC), reaction mixture quenched with IN NaOH solution and extracted with DCM (2 x 250 mL). Combined organic layers and dried over sodium sulphate andevaporated under reduced pressure to afford 60.0 g of crude Compound 7. The obtained crude compound was purified by column chromatography using silica gel (60-120 mesh) as the stationary phase, eluting with 0-25% ethyl acetate in hexane. Collected the pure fractions and evaporated under vacuum to afford 47.0 g of Compound 7 as a pale-yellow solid (>98% pure by HPLC 260 nm, Mass (m / z): 270.11 [M+H]+)

[0213] 1H NMR (400 MHz, DMSO-d6): 5 7.55 (dd, J=2.0 Hz, 1H), 7.52 (t, J=1.6 Hz,1H), 7.50 (t, J=9.6 Hz, 1H), 6.92 (dd, J=8.8 Hz, 1H), 6.38 (dd, J=12.8 Hz, 1H), 6.35 (dd, J=4.8 Hz, 2H), 6.34 (d, J=1.6 Hz, 1H), 6.26 (dd, J=3.2 Hz, 1H), 6.18 (dd, J=3.2 Hz, 1H), 6.08 (t, J=5.6 Hz, 1H), 5.31 (t, J=6.4 Hz, 1H), 4.32 (d, J=6.0 Hz, 2H), 4.14 (d, J=6.4 Hz, 2H)

[0214] 13C NMR (100 MHz, DMSO-d6): 5 154.81, 154.09, 151.87, 142.30, 141.98,136.72, 131.95, 124.95, 110.79, 109.25, 107.35, 106.67.EXAMPLE 9Synthesis of N3,N6-bis(5-methylhexan-2-yl)pyridazine-3,6-diamine (Compound 86)

[0215] To a stirred solution of 6-bromopyridazin-3 -amine (50.0 g, 0.289 mol) in MIAK (500 mL) was added acetic acid (500 mL) at RT, followed by the addition of NaCNBH? (55.0 g, 0.867 mol), portion wise at RT for 30 min. The resulting reaction contents were stirred at RT for 48 h. After completion of reaction (monitored by TLC), quenched the reaction with ice-cold water and extracted with ethyl acetate (2 x 500 mL). The combined organic layers were dried over sodium sulphate, filtered and evaporated under vacuum to afford 150 g of crude Intermediate 86-1.

[0216] Purification: Crude Intermediate 86-1 was purified by silica gel column chromatography (100-200 mesh) eluting with 10-15% ethyl acetate in hexane to afford Intermediate 86-1 as a pale-yellow gummy liquid.Step 2

[0217] A stirred solution of Intermediate 86-1 (40.0 g, 0.147 mol) in dry DMSO (400 mL) was degassed with nitrogen for 15-20 min, followed by the addition of 4-Hydroxy-L- Proline (7.7 g, 0.059 mol), Cui (5.6 g, 0.029 mol) and potassium carbonate (41.0 g, 0.294 mol). After stirring for 10 min, 5-methylhexan-2-amine (85.0 g, 0.735 mol) was added at RT and then heated to 85-90°C. The resulting reaction mass was stirred at 85-90°C for 48 h. After completion of reaction (monitored by TLC), cooled to RT, filtered through celite bed and washed the bed with DCM (500 mL). And total filtrate was collected and evaporated under vacuum to afford 80 g of crude Compound 86. Compound 86 was purified by silica gel column chromatography (100-200 mesh) eluting with 45-50% ethyl acetate in hexane to afford Compound 86 as a brown liquid, which was further purified by reverse phase biotage by eluting in 45-50% ACN in water and collected pure fractions, which were evaporated under reduced pressure to afford 9.9 g Compound 86 as thick gummy liquid (>99% pure by HPLC 260 nm, Mass (m / z): 307.30 [M+H]+).EXAMPLE 10Synthesis of N3-(4-methylpentan-2-yl)-N6-phenylpyridazine-3,6-diamine (Compound 13)Step 1

[0218] To a stirred solution of 6-bromopyridazin-3 -amine (120 g, 0.68 mol) in AcOH (600 mL) was added MIBK (1200 L) and stirred for 10 min. Cooled to 20-25°C and added NaCNBHi (130 g, 2.06 mol) as portion wise, maintained for 48 hr.at RT. After completion of the reaction, (monitored by TLC), reaction mixture quenched with Sat. NaHCCh solution. Separated organic layer and Aqueous layer extracted with DCM (2 x 250 mL). Combined organic layers and dried over sodium sulphate and evaporated under reduced pressure to afford 187.0 g of crude Intermediate 13-1 which was purified by column chromatography using silica gel (60-120 mesh) as the stationary phase, eluting with 15-20% ethyl acetate in hexane. Collected the pure fractions and evaporated under vacuum to afford 34.0 g of desired compound Intermediate 13-1 as a light brown liquid.Step 2

[0219] Taken Intermediate 13-1 (58.0 g, 0.21mol) into an autoclave and added aniline (280 mL, 5.0 vol) and heated to 120 °C and maintained for 16 h. After completion of the reaction (monitored by TLC), cooled to RT and diluted with DCM (500 mL). Evaporated under reduced pressure at 45°C to give 120.0 g of crude Compound 13. The material was purified by column chromatography using silica gel (60-120mesh) as the stationary phase, eluting with 0-10% methanol in DCM. Collected the pure fractions and evaporated under vacuum to afford desired 47.0 g of Compound 13 as a brown solid (>99% purity by HPLC 260 nm, Mass (m / z): 271.20[M+H]+).

[0220] 1H NMR (400 MHz, DMSO-de): 5 8.60 (s, 1H), 7.64 (d, J=7.6 Hz, 2H), 7.21 (t,J=7.2 Hz, 2H), 6.90 (d, J=9.2Hz, 1H), 6.80 (t, J=7.2Hz, 1H), 6.75 (d, J=9.6 Hz, 1H), 6.00(d, J=8.0Hz 1H), 4.06-4.03(m, 1H), 1.71-1.78 (m, 1H), 1.47-1.50 (m, 1H),1.26-I.24(m, 1H), 1.10 (d, J=6.4 Hz, 3H), 0.88 (dd, J=6.8 Hz, 6H)

[0221] 13C NMR (100 MHZ, DMSO-de): 5 154.61, 151.24, 142.79, 129.00, 120.43, 119.81, 119.02, 117.38, 46.36, 44.28, 40.63, 40.42, 40.21, 40.01, 39.80, 39.59, 39.38, 25.06, 23.19, 23.03, 21.45EXAMPLE 11Synthesis of N2-(4-methylpentan-2-yl)-N5-phenylpyrimidine-2,5-diamine (Compound 22)

[0222] To a stirred solution of 5-bromopyrimidin-2-amine (50.0 g, 0.289 mol) in DMF (1.5 L) was added KOlBu (97.1 g, 0.867 mol) and stirred for 5 min, followed by the addition of 4-methylpentan-2-yl 4-methylbenzenesulfonate (295.9 g, 1.156 mol) dissolved in DMF (1.0 L). The resulting reaction contents were heated at 85-90°C and stirred for 16 h. After completion of reaction (monitored by TLC), quenched the reaction with chilled water (2.5 L) and extracted with DCM (2.5 L). Separated the organic layer, dried over sodium sulphate, filtered and evaporated under vacuum to afford 100 g of crude Intermediate 22-1 which was purified by silica gel column chromatography (100- 200 mesh) eluting with 6-8% ethyl acetate in hexane to afford 32.8 g of Intermediate 22-1 as a pale-yellow solid.Step 2

[0223] Purged nitrogen into toluene (1.9 L) for 30 min, followed by the addition of Pd2dba3 (13.5 g, 0.015 mol) and X-Phos (21.1 g, 0.044 mol). After purging the reaction mixture with nitrogen for 15-20 min, Intermediate 22-1 (38.0 g, 0.147 mol) and aniline (15.13 g, 0.162 mol) were added followed by the addition of NaOlBu (28.41 g, 0.295 mol). Heated the reaction to 85-90°C and maintained for 16 h. After completion of reaction (monitored by TLC), the reaction mixture was cooled to RT and filtered through a celite pad. The filter cake was thoroughly washed with toluene and the filtrate was evaporated under reduced pressure to get crude residue (120 g). The obtained residue was further purified by silica-gel (100-200 mesh) column chromatography eluting with 12- 15% ethyl acetate in hexane to afford 45.0 g Compound 22 as off-white solid (>99% pure by HPLC 260 nm, Mass (m / z): 271.20 [M+H]+)

[0224] 'H NMR (400 MHz, DMSO-de): 5 8.13 (s, 2H), 7.49 (s, 1H), 7.12 (d, J= 7.6 Hz, 2H), 6.74-6.69 (m, 3H), 6.65 (t, J= 7.2 Hz, 1H), 4.03-3.97 (m, 1H), 1.69-1.61 (m, 1H), 1.52-1.45 (m, 1H), 1.28-1.23 (m, 1H), 1.01 (d, J= 6.4 Hz, 3H), 0.88 (t, J= 6.4 Hz, 6H)

[0225] 13C NMR (100 MHz, DMSO-de): 5 159.47, 154.05, 147.19, 129.64, 126.87,118.13, 113.76, 45.97, 44.67, 25.07, 23.25, 22.92, 21.9EXAMPLE 12Synthesis of N5-(4-methylpentan-2-yl)-N2-phenylpyrimidine-2,5-diamine (Compound 19)Step 1

[0226] Purged nitrogen into 1,4-Dioxane (500 mL) for 30 min, followed by the addition of Pd2dba3 (19.6 g, 0.027 mol) and X-Phos (30.6 g, 0.069 mol). After purging the reaction mixture with nitrogen for 15-20 min, 5-nitropyrimidin-2-amine (50.0 g, 0.357 mol) and bromobenzene (61.7 g, 0.392 mol) were added followed by the addition of KO‘Bu (60.0 g, 0.535 mol). Heated the reaction to 85-90°C and maintained for 16 h. After completion of reaction (monitored by TLC), the reaction mixture was cooled to RT and filtered through a celite pad. The filter cake was thoroughly washed with 1,4-Dioxane and the filtrate was evaporated under reduced pressure to get crude residue (120 g). The obtained residue was further purified by silica-gel (100-200 mesh) column chromatography eluting with 8-12% ethyl acetate in hexane to afford 28 g of Intermediate 19-1 as yellow solid.Step 219-1 19-2

[0227] To a solution of Intermediate 19-1 (37.0 g, 0.171 mol) in methanol (370 mL) was added Raney Ni (15.0 g, 40% w / w) in an autoclave. Hydrogen pressure (15 kgs) was applied to the reaction and stirred for 16 h. After completion of reaction (monitored by TLC), the reaction mixture was filtered through a celite pad. The filter cake was thoroughly washed with methanol and the filtrate was evaporated under reduced pressure to get Intermediate 19-2 (33 g) as a brown gummy compound.Step 3

[0228] To a stirred solution of Intermediate 19-2 (33.0 g, 0.177 mol) in di chloroethane(330 mL) was added MIBK (330 mL) and sodium acetate (58.0 g, 0.709 mol) at RT, followed by the addition of STAB (225.6 g, 1.064 mol) portion wise for 30 min. Stirred the reaction for 16 h at RT. After completion of reaction (monitored by TLC), quenched the reaction with ice-cold water and extracted with ethyl acetate (2 x 400 mL). The combined organic layers were dried over sodium sulphate, filtered and evaporated under vacuum to afford 101 g of crude Compound 19. The crude compound was purified by silica gel column chromatography (100-200 mesh) eluting with 15-20% ethyl acetate in hexane to afford Compound 19 (22.4 g) as a brown gummy compound (>99% pure by HPLC 260 nm, Mass (m / z): 271.20 [M+H]+).

[0229] 1H NMR (400 MHz, DMSO-de): 5 8.98 (s, 1H), 7.96 (s, 2H), 7.67 (d, J= 7.6 Hz,2H), 7.19 (t, J= 7.6 Hz, 2H), 6.80 (t, J= 7.2 Hz, 1H), 5.01 (d, J= 8.8 Hz, 1H), 3.45-3.38 (m, 1H), 1.76-1.68 (m, 1H), 1.45-1.38 (m, 1H), 1.25-1.20 (m, 1H), 1.07 (d, J= 6.0 Hz, 3H), 0.91-0.82 (m, 6H)

[0230] 13C NMR (100 MHz, DMSO-de): 5 152.94, 142.92, 142.28, 136.37, 128.82,119.98, 117.47, 46.38, 24.97, 23.18, 23.04, 20.92EXAMPLE 13Synthesis of N2-(4-methylpentan-2-yl)-N5-phenylpyridine-2,5-diamine (Compound 28)Step 1

[0231] To a stirred solution of 5-bromopyridin-2-amine (100 g, 0.57 mol) in AcOH (500 mL) was added MIBK (1000 L) and stirred for 10 min. Cooled to 20-25 °C and added NaCNBHs (110 g, 1.73 mol) as portion wise, maintained for 16 hr at RT. After completion of the reaction, (monitored by TLC), reaction mixture quenched with Sat. NaHCCh solution. Separated organic layer and aqueous layer extracted with DCM (2 x 250 mL). Combined organic layers and dried over sodium sulphate and evaporated under reduced pressure to afford 200.0 g of crude product. The obtained crude compound was purified by column chromatography using silica gel (60-120 mesh) as the stationary phase, eluting with 5-10% ethyl acetate in hexane. Collected the pure fractions and evaporated under vacuum to afford 102.0 g of Intermediate 28-1 as a light brown liquid.Step 2

[0232] To a stirred toluene (2000 mL) was degassed with nitrogen for 30 mins, followed by the addition of Pd2(dbas) (7.26 g, 0.0039 mol) and X-phos (7.5 g, 0.07 mol) at RT, degassed with nitrogen for 30 min. Heated to 60 °C and maintained for 20 min, followed by the addition of Intermediate 28-1 (102 g, 0.39 mol), aniline (40 mL, 0.016 mol) and NaOlBu (53.3 g, 0.55 mol) at 60 °C. Heated to 90°C and maintained for 16 h. After completion of the reaction (monitored by TLC), cooled to RT and filtered through celite bed and washed bed with EtOAc (500mL), evaporated the filtrate under reduced pressure at 45°C to give 125.0 g of crude compound. The obtained crude compound was purified by column chromatography using silica gel (60-120mesh) as the stationary phase, eluting with 0-3% methanol in DCM. Collected the pure fractions and evaporated under vacuum to afford desired 64.0 g of Compound 28 (>99% pure by HPLC 260 nm, Mass (m / z): 270.15 [M+H]+).

[0233] 1H NMR (400 MHz, DMSO-de): 5 7.78 (d, J=2.8 Hz, 1H), 7.45 (s, 1H), 7.20 (dd,J=8.8 Hz, 1H), 7.09 (t, J=2.8 Hz, 2H), 6.70 (d, J=7.6 Hz, 2H), 6.61 (t, J=7.2 Hz ,1H), 6.43 (d, J=8.4 Hz, 1H), 6.01 (d, J=8.4 Hz ,1H), 3.98-3.90 (m, 1H), 1.69-1.64 (m, 1H), 1.46- 1.40 (m, 1H), 1.25-1.18 (m, 1H), 1.07 (d, J=6.4 Hz, 3H), 1.07 (d, J=6.4 Hz, 3H), 0.88 (d, J=6.8 Hz, 12H)

[0234] 13C NMR (100 MHz, DMSO-de): 5 155.60, 147.46, 142.34, 133.18,129.49,127.97, 117.64, 113.80, 108.85, 46.52, 44.25, 40.62, 40.41, 40.20, 39.99, 39.78, 39.57, 39.37, 25.06, 23.25, 23.04, 21.84EXAMPLE 14Synthesis of 6-methyl-N2-(4-methylpentan-2-yl)-N5-phenylpyridine-2,5-diamine (Compound 70)

[0235] To a stirred solution of 5-bromo-6-methylpyridin-2-amine (100.0 g, 0.537 mol) in AcOH (1.0 L) was added MIBK (1.0 L) at RT, followed by the addition of NaBHsCN (166.0 g, 2.688 mol) portion wise for 30 min. Stirred the reaction for 16 h at RT. After completion of reaction (monitored by TLC), quenched the reaction with ice-cold water and extracted with ethyl acetate (2 x 1.0 L). The combined the organic layers were dried over sodium sulphate, filtered and evaporated under vacuum to afford 200 g of crude compound. The crude compound was purified by silica gel column chromatography (100- 200 mesh) eluting with 10-15% ethyl acetate in hexane to afford 90.0 g of Intermediate 70-1 as a brown gummy liquid.Step 2

[0236] Purged nitrogen into 1,4-Dioxane (750 mL) for 30 min, followed by the addition of Pchdbas (17.0 g, 0.018 mol) and X-Phos (26.4 g, 0.55 mol). After purging the reaction mixture with nitrogen for 15-20 min, Intermediate 70-1 (50.0 g, 0.18 mol) and aniline (18.6 mL, 0.20 mol) were added followed by the addition of KOtBu (31.2 g, 0.28 mol). Heated the reaction to 85-90°C and maintained for 16 h. After completion of reaction (monitored by TLC), the reaction mixture was cooled to RT and filtered through a celite pad. The filter cake was thoroughly washed with 1,4-Dioxane and the filtrate was evaporated under reduced pressure to get crude residue (95 g). The obtained residue was further purified by silica-gel (100-200 mesh) column chromatography eluting with 4-6% ethyl acetate in hexane to afford 26.5 g of Compound 70 as pale-yellow solid (>99% purity by HPLC 260 nm, Mass (m / z): 284.25 [M+H]+).

[0237] 1H NMR (400 MHz, DMSO-de): 5 7.11 (d, J= 8.8 Hz, 1H), 7.07-7.03 (m, 2H),6.55 (t, J= 7.2 Hz, 1H), 6.48 (d, J= 7.6 Hz, 2H), 6.27 (d, J= 8.4 Hz, 1H), 5.98 (d, J= 8.4 Hz, 1H), 3.97-3.89 (m, 1H), 2.14 (s, 3H), 1.69-1.64 (m, 1H), 1.47-1.41 (m, 1H), 1.24-1.16 (m, 1H), 1.08 (d, J= 6.4 Hz, 3H), 0.90 (d, J= 6.8 Hz, 3H), 0.87 (d, J= 6.8 Hz, 3H)

[0238] 13C NMR (100 MHz, DMSO-de): 5 156.03, 152.87, 148.42, 136.43, 129.41,124.57, 116.86, 113.20, 106.02, 46.69, 44.25, 25.09, 23.29, 23.10, 21.82, 21.17EXAMPLE 15Synthesis of 3-methyl-N2-(4-methylpentan-2-yl)-N5-phenylpyridine-2,5-diamine (Compound 71)Step 1

[0239] To a stirred solution of 5-bromo-3-methylpyridin-2-amine (150 g, 0.80 mol) in AcOH (750 mL) was added MIBK (1500 L) and stirred for 10 min. Cooled to 20-25 °C and added NaCNBHs (151 g, 2.40 mol) as portion wise, maintained for 16 hr at RT. After completion of the reaction, (monitored by TLC), reaction mixture quenched with Sat. NaHCCh solution. Separated organic layer and Aq. layer extracted with DCM (2 x 250 mL). Combined organic layers and dried over sodium sulphate and evaporated under reduced pressure to afford 250.0 g of crude Intermediate 71-1.

[0240] The obtained crude compound was purified by column chromatography using silica gel (60-120 mesh) as the stationary phase, eluting with 15-20% ethyl acetate in hexane. Collected the pure fractions and evaporated under vacuum to afford 104.0 g of Intermediate 71-1 as a yellow liquid.Step 2

[0241] A stirred toluene (2000 mL) was degassed with nitrogen for 30 mins, followed by the addition of Pd2(dbas) (7.0 g, 0.0076 mol) and X-phos (7.3 g, 0.015 mol) at RT, degassed with nitrogen for 30 min. Heated to 60 °C and maintained for 20 min, followed by the addition of Intermediate 71-1(104 g, 0.38 mol), aniline (39.3 g,0.42 mol) and NaOlBu (51.6 g, 0.53 mol) at 60 °C. Heated to 90°C and maintained for 16 h°C. After completion of the reaction (monitored by TLC), cooled to RT and filtered through celite bed and washed bed with EtOAc (500mL), evaporated the filtrate under reduced pressure at 45°C to give 145.0 g of crude Compound 71. The obtained crude was purified by column chromatography using silica gel (60-120mesh) as the stationary phase, eluting with 0-3% methanol in DCM. Collected the pure fractions and evaporated under vacuumto afford 65.0 g of Compound 71 as a brown gummy liquid (>99% pure by HPLC 260 nm, Mass (m / z): 284.07 [M+H]+).

[0242] 1H NMR (400 MHz, DMSO-de): 5 7.71 (d, J=2.0 Hz, 1H), 7.43 (s, 1H), 7.09 (dd,J=6.8 Hz, 3H), 6.72 (d, J=7.6Hz, 2H), 6.60 (t, J=7.2Hz, 1H), 5.10 (d, J=8.4 Hz, 1H), 4.26- 4.16 (m, 1H), 2.03 (s, 3H), 1.74-1.64 (m, 1H), 1.59-1.52 (m, 1H), 1.29-1.23 (m, 1H), 1.10 (d, J=6.4 Hz, 3H), 0.88 (dd, J=6.8 Hz, 6H)

[0243] 13C NMR (100 MHz, DMSO-de): 5 153.66, 147.51, 139.49, 133.04, 129.45,128.16, 117.59, 117.28, 113.90, 46.39, 44.18, 40.62, 40.41, 40.21, 40.00, 39.79, 39.58, 39.37, 25.19, 23.27, 23.11, 21.90, 17.52EXAMPLE 16Synthesis of N5-(4-methylpentan-2-yl)-N2-phenylpyridine-2,5-diamine (Compound 25)

[0244] To a stirred solution of 2-bromo-5-nitropyridine (100 g, 0.80 mol) in methanol (500 mL) was added iron powder (110.0 g, 1.97 mol) and stirred for 10 min. NH4Q solution (105 g, 1.97 mol in 400 mL of water) was added dropwise. Heated to 70 °C and maintained for 3-4 hr. After completion of the reaction, (monitored by TLC), reaction mixture cooled to RT and filtered through celite pad. Washed with methanol (100 mL). Filtrate evaporated under reduced pressure to afford crude. Obtained crude dissolved in DCM and washed with Sat. NaCl solution. Separated organic layers dried over sodium sulphate and evaporated under reduced pressure to afford 96.0 g of crude Intermediate 25- 1. The obtained crude compound was purified by column chromatography using silica gel (60-120 mesh) as the stationary phase, eluting with 15-20% ethyl acetate in hexane. Collected the pure fractions and evaporated under vacuum to afford 80.0 g of Intermediate 25-1 as a brown solid.Step 2

[0245] To a stirred solution of Intermediate 25-1 (80 g, 0.46 mol) in AcOH (400 mL) was added MIBK (800 L) and stirred for 10 min. Cooled to 20-25 °C and added NaCNBHi (87 g, 1.38 mol) as portion wise, maintained for 16 hr at RT. After completion of the reaction, (monitored by TLC), reaction mixture quenched with Sat. NaHCCh solution. Separated organic layer and Aq. layer extracted with DCM (2 x 250 mL). Combined organic layers and dried over sodium sulphate and evaporated under reduced pressure to afford 195.0 g of crude Intermediate 25-2. The obtained crude compound was purified by column chromatography using silica gel (60-120 mesh) as the stationary phase, eluting with 5-10% ethyl acetate in hexane. Collected the pure fractions and evaporated under vacuum to afford 125.0 g of Intermediate 25-2 as a brown liquid.Step 3

[0246] To a stirred toluene (2500 mL) was degassed with nitrogen for 30 mins, followed by the addition of Pd2(dbas) (8.9 g, 0.009 mol) and X-phos (9.2 g, 0.019 mol) at RT, degassed with nitrogen for 30 min. Heated to 60 °C and maintained for 20 min, followed by the addition of Intermediate 25-2 (125 g, 0.48 mol), aniline (50 mL,0.53 mol) and NaOlBu (65 g, 0.68 mol) at 60 °C. Heated to 90°C and maintained for 16 h. After completion of the reaction (monitored by TLC), cooled to RT and filtered through celite bed and washed bed with EtOAc (500mL), evaporated the filtrate under reduced pressure at 45°C to give 175.0 g of crude compound 25. The obtained the crude compound was purified by column chromatography using silica gel (60-120 mesh) as the stationary phase, eluting with 8-10% ethyl acetate in hexane, collected the pure fractions and evaporated under reduced pressure to afford 50.0 g of Compound 25 as a brown oil (>99% purity by HPLC 260 nm, Mass (m / z): 270.29 [M+H]+).

[0247] 'H NMR (400 MHz, DMSO-de): 5 8.40 (s, 1H), 7.58 (d, J=2.8 Hz, 1H), 7.49 (dd, J=8.4 Hz, 2H), 7.16 (t, J=7.2 Hz, 2H), 6.95 (dd, J=8.8 Hz, 1H), 6.70 (dd, J=7.2 Hz, 1H), 4.83 (d, J=8.8 Hz 1H), 3.41-3.33 (m, 1H), 1.76-1.71 (m, 1H), 1.45-1.39 (m, 1H), 1.25- 1.19 (m, 1H), 1.17 (d, J=3.6 Hz, 3H), 1.10 (dd, J=3.6 Hz, 6H)

[0248] 13C NMR (100 MHZ, DMSO-de): 5 147.30, 143.75, 138.56, 131.49, 128.96, 124.02, 118.90, 116.49, 112.31, 46.49, 40.61, 40.40, 40.20, 39.99, 39.78, 39.57, 39.36, 25.00, 23.23, 23.04, 21.11.EXAMPLE 17Synthesis of 4-methyl-N5-(4-methylpentan-2-yl)-N2-phenylpyridine-2,5-diamine (Compound 87)Step 187-1

[0249] To a stirred solution of 2-chloro-4-methyl-5-nitropyridine (150 g, 0.86 mol) in methanol (750 mL) was added Iron powder (194.0 g, 3.47 mol) and stirred for 10 min. NH4Q solution (187 g, 1.97 mol in 600 mL of water) was added dropwise. Heated to 70 °C and maintained for 3-4 hr. After completion of the reaction, (monitored by TLC), reaction mixture cooled to RT and filtered through celite pad. Washed with methanol (150 mL). Filtrate evaporated under reduced pressure to afford crude. Obtained crude dissolved in DCM and washed with Sat. NaCl solution. Separated organic layers dried over sodium sulphate and evaporated under reduced pressure to afford 130.0 g of Intermediate 87-1. The obtained crude compound was purified by column chromatography using silica gel (60-120 mesh) as the stationary phase, eluting with 15-20% ethyl acetate in hexane. Collected the pure fractions and evaporated under vacuum to afford 110.0 g of Intermediate 87-1 as an off-white solid.Step 287-1 87-2

[0250] To a stirred solution of Intermediate 87-1 (110 g, 0.77 mol) in AcOH (550 mL) was added MIBK (1100 L) and stirred for 10 min. Cooled to 20-25 °C and added NaCNBHi (87 g, 2.32 mol) portion wise, maintained for 16 hr at RT. After completion of the reaction, (monitored by TLC), reaction mixture quenched with Sat. NaHCCh solution. Separated organic layer and aqueous layer extracted with DCM (2 x 250 mL). Combined organic layers and dried over sodium sulphate and evaporated under reduced pressure to afford 210.0 g of crude Intermediate 87-2. The obtained crude compound was purified by column chromatography using silica gel (60-120 mesh) as the stationary phase, eluting with 3-5% ethyl acetate in hexane. Collected the pure fractions and evaporated under vacuum to afford 160.0 g of Intermediate 87-2 as an off-white solid.Step 3

[0251] A stirred solution of toluene (3200 mL) was degassed with nitrogen for 30 mins, followed by the addition of Pd2(dbas) (38.0 g, 0.04 mol) and X-phos (27 g, 0.05 mol) at RT, degassed with nitrogen for 30 min. Heated to 60 °C and maintained for 20 min, followed by the addition of Intermediate 87-2 (160 g, 0.70 mol), aniline (73 mL,0.77 mol) and NaOlBu (102.0 g, 1.06 mol) at 60 °C. Heated to 90°C and maintained for 16 h. After completion of the reaction (monitored by TLC), cooled to RT and filtered through celite bed and washed bed with EtOAc (500mL), evaporated the filtrate under reduced pressure at 45°C to give 195.0 g of crude Compound 87. The obtained the crude compound waspurified by column chromatography using silica gel (60-120 mesh) as the stationary phase, eluting with 0-10% ethyl acetate in hexane, collected the pure fractions and evaporated under reduced pressure to afford 55.0 g of Compound 87 as an off-white solid (>99% pure by HPLC 260 nm, Mass (m / z): 284.11 [M+H]+).

[0252] 1H NMR (400 MHz, DMSO-de): 5 8.40 (s, 1H), 7.58 (d, J=2.8 Hz, 1H), 7.49 (dd,J=8.4 Hz, 2H), 7.16 (t, J=7.2 Hz, 2H), 6.95 (dd, J=8.8 Hz, 1H), 6.70 (dd, J=7.2 Hz, 1H), 4.83 (d, J=8.8 Hz 1H), 3.41-3.33 (m, 1H), 1.76-1.71 (m, 1H), 1.45-1.39 (m, 1H), 1.25- 1.19 (m, 1H), 1.17 (d, J=3.6 Hz, 3H), 1.10 (dd, J=3.6 Hz, 6H)

[0253] 13C NMR (100 MHz, DMSO-de): 5 147.30, 143.75, 138.56, 131.49, 128.96,124.02, 118.90, 116.49, 112.31, 46.49, 40.61, 40.40, 40.20, 39.99, 39.78, 39.57, 39.36, 25.00, 23.23, 23.04, 21.11.EXAMPLE 18Synthesis of 6-methyl-N5-(4-methylpentan-2-yl)-N2-phenylpyridine-2,5-diamine (Compound 64)

[0254] Purged nitrogen into 1,4-Dioxane (600 mL) for 30 min, followed by the addition of Pd2dba3 (35.8 g, 0.039 mol) and X-Phos (56.0 g, 0.12 mol). After purging the reaction mixture with nitrogen for 15-20 min, 6-methyl-5-nitropyridin-2-amine (60.0 g, 0.39 mol) and bromobenzene (46.0 mL, 0.43 mol) were added followed by the addition of KOtBu (65.8 g, 0.59 mol). Heated the reaction to 85-90°C and maintained for 16 h. After completion of reaction (monitored by TLC), the reaction mixture was cooled to RT and filtered through a celite pad. The filter cake was thoroughly washed with 1,4-Dioxane and the filtrate was evaporated under reduced pressure to get crude residue (130 g). The obtained residue was further purified by silica-gel (100-200 mesh) column chromatography eluting with 10-15% ethyl acetate in hexane to afford Intermediate 64-1 as yellow solid.Step 2

[0255] To a solution of Intermediate 64-1 (47.0 g, 0.20 mol) in methanol (500 mL) was added Raney Ni (15.0 g, 30% w / w) in an autoclave. Hydrogen pressure (15 kgs) was applied to the reaction and stirred for 16 h. After completion of reaction (monitored by TLC), the reaction mixture was filtered through a celite pad. The filter cake was thoroughly washed with methanol and the filtrate was evaporated under reduced pressure to get crude Intermediate 64-2 (42 g) as a brown gummy compound.Step 3

[0256] To a stirred solution of Intermediate 64-2 (40.6 g, 0.205 mol) in di chloroethane (406 mL) was added MIBK (406 mL) and sodium acetate (67.0 g, 0.820 mol) at RT, followed by the addition of STAB (259.0 g, 1.230 mol) portion wise for 30 min. Stirred the reaction for 16 h at RT. After completion of reaction (monitored by TLC), quenched the reaction with ice-cold water and extracted with ethyl acetate (2 x 400 mL). Thecombined organic layers were dried over sodium sulphate, filtered and evaporated under vacuum to afford 120 g of crude Compound 64. The crude compound was purified by silica gel column chromatography (100-200 mesh) eluting with 15-20% ethyl acetate in hexane to afford 37.7 g of Compound 64 as a brown gummy liquid (>97% pure by HPLC 260 nm, Mass (m / z): 284.11 [M+H]+).

[0257] XH NMR (400 MHz, DMSO-de): 5 8.33 (s, 1H), 7.49 (d, J= 8.0 Hz, 1H), 7.16 (t, J= 8.4 Hz, 2H), 6.93 (d, J= 8.8 Hz, 1H), 6.72 (t, J= 7.2 Hz, 1H), 6.65 (d, J= 8.4 Hz, 1H), 3.90 (d, J= 8.8 Hz, 1H), 3.42-3.37 (m, 1H), 2.27 (s, 3H), 1.78-1.71 (m, 1H), 1.54-1.47 (m, 1H), 1.28-1.21 (m, 1H), 1.08 (d, J= 6.0 Hz, 3H), 0.91 (d, J= 6.8 Hz, 3H), 0.87 (d, J= 6.8 Hz, 3H)

[0258] 13C NMR (100 MHz, DMSO-de): 5 146.42, 144.02, 141.45, 135.72, 128.97,121.58, 118.82, 116.45, 109.38, 46.96, 46.48, 25.09, 23.29, 23.03, 21.19, 21.15EXAMPLE 19Oxidative Induction Time (OIT) Performance of Compounds of the Disclosure

[0259] The oxidative induction times (OIT) of Compounds of the Disclosure were 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.

[0260] 0.5 phr of Compound 1, N1-(4-methylpentan-2-yl)-N4-phenylbenzene-l,4-diamine(6PPD as control), or no antidegradant (blank) was mixed with liquid polyisoprene (cis) polymer having an average molecular weight of about 35,000 and heated isothermally at 150 °C or 160 °C in O2. The OIT in minutes is shown in Table 3. As indicated by the data in Table 3, Compound 1 demonstrates antioxidant activity compared to the blank control.

[0261] In addition, the experimental glass transition temperature (Tg) was measured for Compound 1, and is listed in Table 3.

[0262] 0.5 phr of a Compound of the Disclosure, N1-(4-methylpentan-2-yl)-N4- phenylbenzene-l,4-diamine (6PPD as control), or no antidegradant (blank) was mixed with liquid polyisoprene polymer having an average molecular weight of about 28,000 and heated isothermally at 150 °C or 160 °C in O2. The OIT in minutes is shown in Table4. As indicated by the data in Table 4, Compounds of the Disclosure demonstrate antioxidant activity compared to the blank control.

[0263] In addition, the experimental glass transition temperatures (Tg) were measured for Compounds of the disclosure, and are listed in Table 4.Table 3Table 4

[0264] 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 (I):or a salt, solvate, or stereoisomer thereof, wherein:X1, X2, and X3are each independently selected from the group consisting of -CR- and -N-;R is at each occurrence independently selected from the group consisting of hydrogen, C1-C9 alkyl, C1-C9 alkoxy, and C1-C9 alkylthio;R1is selected from the group consisting of C1-C12 alkyl, -CHRlaRlb, C3-C6 cycloalkyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;Rlais selected from the group consisting of optionally substituted phenyl, C3-C6 cycloalkyl, and optionally substituted 5- or 6-membered heteroaryl;Rlbis independently selected from the group consisting of hydrogen and Ci-Ce alkyl;R2is selected from the group consisting of C1-C12 alkyl, -CHR2aR2b, C3-C6 cycloalkyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;R2ais selected from the group consisting of optionally substituted phenyl, C3-C6 cycloalkyl, and optionally substituted 5- or 6-membered heteroaryl;R2bis independently selected from the group consisting of hydrogen and Ci-Ce alkyl; andR3and R4are each independently selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, and tert-butyl; with provisos that:(i) if R1and R3are both methyl, both n-propyl, or both iso-propyl, R2is not optionally substituted phenyl, or(ii) if R2and R4are both methyl, both n-propyl, or both iso-propyl, R1is not optionally substituted phenyl, or(iii) if X1and X2are -CH-, X3is -N-, R1is iso-propyl, and R3and R4are hydrogen, R2is not phenyl, or(iv) if X1and X2are -CH-, X3is -N-, R1is 4-(dimethylamino)phenyl, and R3and R4are hydrogen, R2is not 4-(dimethylamino)phenyl.

2. The compound of claim 1, or a salt, solvate, or stereoisomer thereof, wherein R3and R4are independently selected from the group consisting of hydrogen and methyl.

3. The compound of claim 1 or 2, or a salt, solvate, or stereoisomer thereof, having Formula (II):(II).

4. The compound of claim 1 or 2, or a salt, solvate, or stereoisomer thereof, having Formula (III):

5. The compound of claim 1 or 2, or a salt, solvate, or stereoisomer thereof, having Formula (IV):

6. The compound of claim 1 or 2, or a salt, solvate, or stereoisomer thereof, having Formula (V):

7. The compound of claim 1 or 2, or a salt, solvate, or stereoisomer thereof, having Formula (VI):(VI).

8. The compound of claim 1 or 2, or a salt, solvate, or stereoisomer thereof, having Formula (VII):(VII).

9. The compound of any one of claims 1-8, or a salt, solvate, or stereoisomer thereof, wherein R3and R4are hydrogen.

10. The compound of any one of claims 1-9, or a salt, solvate, or stereoisomer thereof, wherein R1is C1-C12 alkyl.

11. The compound of claim 10, or a salt, solvate, or stereoisomer thereof, wherein R1is methyl, ethyl, propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, or nonyl.

12. The compound of claim 11, or a salt, solvate, or stereoisomer thereof, wherein R1is iso-propyl.

13. The compound of claim 11, or a salt, solvate, or stereoisomer thereof, wherein R1is:

14. The compound of any one of claims 1-9, or a salt, solvate, or stereoisomer thereof, wherein R1is optionally substituted phenyl.

15. The compound of any one of claims 1-9, or a salt, solvate, or stereoisomer thereof, wherein R1is -CHRlaRlb.The compound of claim 15, or a salt, solvate, or stereoisomer thereof, wherein:Rlais selected from the group consisting of:Q1is -NH-, -O-, or -S-; and Rlbis hydrogen.

17. The compound of claim 16, or a salt, solvate, or stereoisomer thereof, wherein Q1is -O-.

18. The compound of any one of claims 1-17, or a salt, solvate, or stereoisomer thereof, wherein R2is C1-C12 alkyl.

19. The compound of claim 18, or a salt, solvate, or stereoisomer thereof, wherein R2is methyl, ethyl, propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, or nonyl.

20. The compound of claim 19, or a salt, solvate, or stereoisomer thereof, wherein R2is iso-propyl.

21. The compound of claim 18, or a salt, solvate, or stereoisomer thereof, wherein R2is:

22. The compound of any one of claims 1-17, or a salt, solvate, or stereoisomer thereof, wherein R2is optionally substituted phenyl.

23. The compound of any one of claims 1-17, or a salt, solvate, or stereoisomer thereof, wherein R2is -CHR2aR2b.

24. The compound of claim 23, or a salt, solvate, or stereoisomer thereof, wherein:R2ais selected from the group consisting of:Q2is -NH-, -O-, or -S-; andR2bis hydrogen.

25. The compound of claim 24, or a salt, solvate, or stereoisomer thereof, wherein Q2is -O-.

26. The compound of claim 1, or a salt, solvate, or stereoisomer thereof, selected from the group consisting of:

27. A composition comprising:(i) the compound of any one of claims 1-26; 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 antidegradants; 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.

28. The composition of claim 27, wherein the composition comprises one or more elastomers.

29. The composition of claim 28, wherein the composition comprises from about15 wt / wt % to about 85 wt / wt % of the compound and from about 15 wt / wt % to about 85 wt / wt % of the one or more elastomers.

30. The composition of any one of claims 27-29, wherein the one or more elastomers comprise natural rubber (NR).

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

32. The composition of claim 30 or 31, wherein the natural rubber comprises rubber derived from an alternative rubber plant.

33. The composition of claim 32, wherein the alternative rubber plant is Parthenium argentatum (guayule) or Taraxacum kok-saghyz (Russian dandelion).

34. The composition of any one of claims 28-33, wherein the one or more elastomers comprise synthetic rubber.

35. The composition of claim 34, 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.

36. The composition of claim 35, 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.

37. The composition of claim 36, wherein the unsaturated rubber comprises styrene butadiene rubber (SBR).

38. The composition of claim 37, wherein the one or more elastomers comprise from about 5 wt / wt % to about 80 wt / wt % styrene butadiene rubber (SBR).

39. The composition of any one of claims 36-38, wherein the unsaturated rubber comprises polybutadiene rubber (BR).

40. The composition of claim 39, wherein the one or more elastomers comprise from about 5 wt / wt % to about 80 wt / wt % polybutadiene rubber (BR).

41. The composition of any one of claims 36-40, wherein the unsaturated rubber comprises butyl rubber (IIR).

42. The composition of claim 41, wherein the one or more elastomers comprise from about 1 wt / wt % to about 30 wt / wt % butyl rubber (IIR).

43. The composition of any one of claims 35-42, wherein the saturated rubber comprises acrylic rubber (ACM), chlorinated polyethylene (CM), chlorosulfonated polyethylene (CSM), polychloromethyloxiran (CO), ethylene-ethyl acrylate copolymer (EAM), epichlorohydrin rubber (ECO), ethylene propylene rubber (EPM), ethylenevinylacetate copolymer (EVM), or a blend thereof.

44. The composition of claims any one of claims 27-43, wherein the one or more elastomers further comprises recycled rubber.

45. The composition of any one of claims 27-44, wherein the composition comprises from about 0.1 phr to about 10 phr of the compound.

46. The composition of claim 45, wherein the composition comprises from about 0.5 phr to about 5 phr of the compound.

47. The compound of claim 46, wherein the composition comprises from about 1 phr to about 5 phr of the compound.

48. The composition of any one of claims 27-47, wherein the composition comprises one or more fillers.

49. The composition of claim 48, wherein the composition comprises from about 15 wt / wt % to about 85 wt / wt % of the compound and from about 15 wt / wt % to about 85 wt / wt % of the one or more fillers.

50. The composition of claims 48 or 49, wherein the composition comprises from about 30 phr to about 500 phr of one or more fillers.

51. The composition of any one of claims 48-50, 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.

52. The composition of claim 51, wherein the one or more fillers comprise silica.

53. The composition of claim 52, wherein the silica is derived from rice husks.

54. The composition of any one of claims 48-53, wherein the one or more fillers comprise carbon black.

55. The composition of any one of claims claim 47-54, wherein the composition comprises one or more rubber chemicals.

56. The composition of claim 55, wherein the composition comprises from about15 wt / wt % to about 85 wt / wt % of the compound and from about 15 wt / wt % to about 85 wt / wt % of one or more rubber chemicals.

57. The composition of claims 55 or 56, wherein the composition comprises from about 0.1 phr to about 30 phr of one or more rubber chemicals.

58. The composition of claim 57, wherein the composition comprises from about 1 phr to about 20 phr of one or more rubber chemicals.

59. The composition of any one of claims 55-58, 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.

60. The composition of claim 59, wherein the one or more rubber chemicals comprise one or more vulcanizing agents.

61. The composition of claim 60, wherein the one or more vulcanizing agents comprise sulfur, peroxide, resin, or a combination thereof.

62. The composition of claim 61, wherein the sulfur is octasulfur (Ss), cyclododecasulfur (S12), polymeric sulfur, or a combination thereof.

63. The composition of claim 61, 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.

64. The composition of claim 61, wherein the resin is a bonding resin.

65. The composition of claims 59-64, wherein the one or more rubber chemicals comprise one or more accelerators.

66. The composition of claim 65, 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.

67. The composition of claim 66, wherein the guanidine is diphenylguanidine (DPG).

68. The composition of claim 66, wherein the thiazole comprises 2-mercaptobenzothiazole (MBT), zinc 2-mercaptobenzothiazole (ZMBT), mercaptobenzothiazole disulfide (MBTS), V- / ert-butyl-2 -benzothiazole sulfenimide (TBSI), or a combination thereof.

69. The composition of claim 66, wherein the sulfenamide comprises V- / c / 7-butyl-2- benzothiazylsulfenamide (TBBS), 7V-cyclohexylbenzothiazol-2-sulfenamide (CBS),dicyclohexyl-2-benzothiazolesulfenamide (DCBS), A -oxy di ethylene benzothiazole sulfenamide (OBTS), 7V-oxydiethylenethiocarbamyl-7V-oxydiethylene sulfenamide (OTOS), thiocarbamyl sulfenamide, or a combination thereof.

70. The composition of claim 66, 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.

71. The composition of claim 66, wherein the dithiocarbamate comprises zinc dimethyldithiocarbamate (ZDMC), zinc diethyldithiocarbamate (ZDEC), zinc dibutyl di thiocarbamate (ZDBC), nickel dibutyl dithiocarbamate (NDBC), sodium dibenzyldithiocarbamate (SBEC), sodium diethyldithiocarbamate (SDEC), tellurium diethyldithiocarbamate (TDEC), zinc dibenzyl dithiocarbamate (ZEBC), or a combination thereof.

72. The composition of any one of claims 59-71, wherein the one or more rubber chemicals comprise one or more activators.

73. The composition of claim 72, wherein the one or more activators comprise a metal oxide, an acid, a metal complex, or a combination thereof.

74. The composition of claim 73, wherein the metal oxide comprises zinc oxide, magnesium oxide, lead oxide, or a combination thereof.

75. The composition of claim 73, wherein the acid comprises stearic acid, lauric acid, or a combination thereof.

76. The composition of claim 73, wherein the metal complex comprises zinc ethylhexanoate.

77. The composition of any one of claims 59-76, wherein the one or more rubber chemicals comprise one or more pre-vulcanization inhibitors.

78. The composition of claim 77, wherein the one or more pre-vulcanization inhibitors comprise 7V-(cyclohexylthio)phthalimide (CTP), benzoic anhydride, salicylic anhydride, phthalic anhydride, or a combination thereof.

79. The composition of any one of claims 27-78, wherein the composition comprises one or more plasticizers.

80. The composition of claim 79, wherein the composition comprises from about15 wt / wt % to about 85 wt / wt % of the compound and from about 15 wt / wt % to about 85 wt / wt % of one or more plasticizers.

81. The composition of claims 79 or 80, wherein the composition comprises from about 0.1 phr to about 30 phr of one or more plasticizers.

82. The composition of claim 81, wherein the composition comprises from about 1 phr to about 20 phr of one or more plasticizers.

83. The composition of any one of claims 79-82, 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.

84. The composition of claim 83, wherein the mineral oil is naphthenic oil, paraffinic oil, or aromatic oil.

85. The composition of claim 83, wherein the naturally derived oil is soybean oil, vegetable oil, or orange oil.

86. The composition of any one of claims 27-85, wherein the composition further comprises one or more additional anti degradants.

87. The composition of claim 86, wherein the composition comprises from about15 wt / wt % to about 85 wt / wt % of the compound and from about 15 wt / wt % to about 85 wt / wt % of the one or more additional anti degradants.

88. The composition of claim 86 or 87, wherein the one or more additional anti degradants is present in an amount of from about 0.001 phr to about 10 phr.

89. The composition of claim 88, wherein the one or more additional anti degradants is present in an amount of from about 0.1 phr to about 5 phr.

90. The composition of claim 89, wherein the one or more additional anti degradants is present in an amount of from about 0.5 phr to about 5 phr.

91. The composition of claim 90, wherein the one or more additional anti degradants is present in an amount of from about 1 phr to about 5 phr.

92. The composition of any one of claims 86-91, wherein the one or more additional anti degradants is an antioxidant.

93. The composition of any one of claims 86-91, wherein the one or more additional anti degradants is an antiozonant.

94. The composition of any one of claims 86-93, wherein the one or more additional anti degradants is a paraphenylenediamine (PPD), a trimethyldihydroquinoline (TMQ), a phenolic, an alkylated diphenylamine (DPA), or a diphenylamine-ketone condensate.

95. The composition of claim 94, wherein the PPD is 7V1-(4-methylpentan-2-yl)-A4- phenylbenzene-l,4-diamine (6PPD), zV-(l ,4-di methyl pentyl )-A'-phenyl-p-phenylenediamine (7PPD), 7V1-phenyl-A4-(propan-2-yl)benzene-l,4-diamine (IPPD), 7V,7V'-di - ec-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).

96. The composition of claim 95, wherein the PPD is 6PPD.

97. The composition of claim 84, wherein the TMQ is 2,2,4-trimethyl-l,2- dihydroquinoline or an oligomer or polymer thereof.

98. A composition comprising the compound of any one of claims 1-26 and one or more carriers.

99. A process for preparing the composition of claim 98, the process comprising admixing the compound and the one or more carriers.

100. A vulcanized elastomeric article comprising the compound of any one of claims 1-26.

101. A vulcanized elastomeric article prepared using the composition of any one of claims 27-98.

102. The vulcanized elastomeric article of claims 100 or 101, wherein the vulcanized elastomeric article is a tire.

103. The vulcanized elastomeric article of claim 102, 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.

104. The vulcanized elastomeric article of claims 100 or 101, wherein the vulcanized elastomeric article is a component of a tire.

105. The vulcanized elastomeric article of claim 104, wherein the component is a bead, a belt, a body ply, an inner liner, a sidewall, an undertread, or a tread.

106. The vulcanized elastomeric article of claims 100 or 101, 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.

107. A process for preparing a vulcanized elastomeric article, the process comprising:(a) forming the composition of any one of claims 28-97 into a formed shape; and(b) vulcanizing the formed shape to provide a vulcanized elastomeric article.

108. The process of claim 107, wherein the vulcanizing is performed at an average temperature of from about 120 °C to about 180 °C.

109. The process of claim 108, wherein the vulcanizing is performed at an average temperature of from about 140 °C to about 160 °C.

110. The process of any one of claims 107-109, wherein the vulcanized elastomeric article is a tire.

111. The process of claim 110, 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.

112. The process of any one of claims 107-111, wherein the vulcanized elastomeric article is a component of a tire.

113. The process of claim 112, wherein the component is a bead, a belt, a body ply, an inner liner, a sidewall, an undertread, or a tread.

114. The process of any one of claims 107-109, 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.

115. A lubricant composition comprising a lubricant and the compound of any one of claims 1-26.

116. A combustible fuel composition comprising a combustible fuel and the compound of any one of claims 1-26.

117. A fuel additive composition comprising a fuel additive and the compound of any one of claims 1-26.

118. A process for retreading tires, the process comprising:(a) applying the composition of any one of claims 27-98 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.

119. A kit comprising the composition of any one of claims 27-98 and instructions for using the composition in a vulcanizable elastomeric composition.

120. A kit comprising the composition of any one of claims 27-98 and instructions for using the composition to prepare a vulcanized elastomeric article.

121. The composition of any one of claims 27, 28, 30-48, 50-55, 57-79, 81-86, or 88- 97, wherein the composition comprises from about 0.1 wt / wt % to about 10 wt / wt % of the compound.

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