Meta-phenylenediamine antidegradant compounds and uses thereof

Abstract

The present disclosure provides compounds represented by Formula (I): (I), or salts or solvates thereof, wherein R1, R1a, R2, R3, R4, X5, R5, R6, R6a, and 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

META-PHENYLENEDI AMINE ANTIDEGRADANT COMPOUNDS AND USES THEREOFBACKGROUNDField

[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 achievethese results while not negatively impacting other additives' efficacy or desirable characteristics in the final article. Further, anti degradants which provide or improve the mechanical fatigue life after an article has been in service, aged oxidatively or by exposure to ozone are highly valued since these will inherently improve the useful mechanical service life of article. Consequently, elastomeric articles which undergo repeated mechanical flexure, extension, or compression during service would greatly benefit from such a discovery.

[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.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)-(XV), 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 antidegradants, 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 t / e-dimethylsulfoxide ( e-DMSO).

[0027] Fig. 2 is a line graph depicting a13C APT NMR spectrum of Compound 1 in c - DMSO.

[0028] Fig. 3 is a line graph depicting a13C APT NMR spectrum of Intermediate Compound 2-1 in e-DMSO.

[0029] Fig. 4 is a line graph depicting a13C APT NMR spectrum of Compound 2 in d- chloroform (CDCh).

[0030] Fig. 5 is a line graph depicting a13C APT NMR spectrum of a mixture of Intermediate Compounds 3-1 and 3-II in tfc-DMSO.

[0031] Fig. 6 is graph depicting a13C APT NMR spectrum of a mixture of Compounds 19 and 20 in tfc-DMSO.DETAILED DESCRIPTION

[0032] In one embodiment, Compounds of the Disclosure are compounds having Formula (I):or a salt, solvate, or stereoisomer thereof, wherein:R1is selected from the group consisting of optionally substituted C1-C12 alkyl, -CHRlcRld, -C(=O)R7, C3-C6 cycloalkyl, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;Rlais selected from the group consisting of hydrogen and C1-C4 alkyl;Rlcis selected from the group consisting of optionally substituted phenyl, 4- to 6- membered heterocyclyl, C3-C6 cycloalkyl, and optionally substituted 5- or 6-membered heteroaryl;Rldis selected from the group consisting of hydrogen and C1-C9 alkyl;R2, R3, and R4are independently selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, Ci-Cs alkoxy, Ci-Cs alkylthio, -C(=O)OR7, -OC(=O)R7, -C(=O)NR7R8, -NR7C(=O)R8, -NR7R8, -OH, -SH,-SC(=O)R7, -SC(=O)SR7, -SC(=O)NR7R8, -NR7C(=O)SR8, -NR7C(=S)SR8, 4- to 6- membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6- membered heteroaryl;X5is selected from the group consisting of -CR5aR5b-, -NR5a-, -O-, and -S-;R5ais absent or is selected from the group consisting of hydrogen and C1-C4 alkyl;R5bis selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, optionally substituted phenyl, -C(=O)OR7, -C(=O)NR7R8, -C(=O)SR7, -CH2OR7, -CH2OC(=O)R7, andR6ais absent or is selected from the group consisting of hydrogen and C1-C4 alkyl;R5is selected from the group consisting of hydrogen, optionally substituted C1-C12 alkyl, -CHR5cR5d, C3-C6 cycloalkyl, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl; orR5and R6taken together with the atoms to which they are attached form an optionally substituted 5- or 6-membered heterocyclyl or an optionally substituted 5- or 6- membered heteroaryl;R5Cis selected from the group consisting of optionally substituted phenyl, 4- to 6- membered heterocyclyl, C3-C6 cycloalkyl, and optionally substituted 5- or 6-membered heteroaryl;R5dis selected from the group consisting of hydrogen and C1-C9 alkyl;R6is selected from the group consisting of optionally substituted C1-C12 alkyl, -CHR6bR6c, C3-C6 cycloalkyl, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl; orR5and R6taken together with the atoms to which they are attached form an optionally substituted 5- or 6-membered heterocyclyl or an optionally substituted 5- or 6- membered heteroaryl;R6bis selected from the group consisting of optionally substituted phenyl, 4- to 6- membered heterocyclyl, C3-C6 cycloalkyl, and optionally substituted 5- or 6-membered heteroaryl;R6Cis selected from the group consisting of hydrogen and C1-C9 alkyl;R7and R8at each occurrence are independently selected from the group consisting of hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl;Z at each occurrence is independently selected from the group consisting of -O-, -S-, and -NR9-;R5e, R5f, R5g, and R5hat each occurrence are independently selected from the group consisting of hydrogen, C1-C12 alkyl, and optionally substituted phenyl; andR9at each occurrence is independently selected from the group consisting of hydrogen and Ci-Ce alkyl.

[0033] In another embodiment, Compounds of the Disclosure are compounds having Formula (I), wherein R1is selected from the group consisting of optionally substituted Ci- C12 alkyl, -CHRlcRld, C3-C6 cycloalkyl, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl.

[0034] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein R5and R6taken together with the atoms to which they are attached form an optionally substituted 5- or 6-membered heterocyclyl or an optionally substituted 5- or 6-membered heteroaryl.

[0035] In some embodiments, Compounds of the Disclosure are compounds having Formula (II):(II), or a salt, solvate, or stereoisomer thereof, wherein:R1, R2, R3, R4, and X5are as defined in connection with Formula (I); when X5is -CR5aR5b- or -NR5a-, then = is a single or a double bond, and when X5is -O- or -S-, then = is a single bond, with the proviso that when = is a double bond, then R5aand R12bare absent;R10is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, optionally substituted phenyl, -C(=O)OR7, -C(=O)NR7R8, -C(=O)SR7, -CH2OR7, -CH2OC(=O)R7, andR11is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl; orR10and R11taken together with the carbon atom to which they are attached form a C3-C12 cycloalkyl; andR12aand R12bare independently selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl.

[0036] In some embodiments, Compounds of the Disclosure are compounds havingFormula (III):(Ill), or a salt, solvate, or stereoisomer thereof, wherein:R1, R2, R3, R4, and R5bare as defined in connection with Formula (I); and R10, R11, and R12aare as defined in connection with Formula (II).

[0037] In some embodiments, Compounds of the Disclosure are compounds having Formula (IV):or a salt, solvate, or stereoisomer thereof, wherein:R1, R2, R3, R4, R5a, and R5bare as defined in connection with Formula (I); and R10, R11, R12a, and R12bare as defined in connection with Formula (II).

[0038] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (II)-(IV), wherein R5bis hydrogen, C1-C9 alkyl, or optionally substituted phenyl.

[0039] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (II)-(IV), wherein R5bis hydrogen, methyl, or optionally substituted phenyl.

[0040] In some embodiments, Compounds of the Disclosure are compounds having Formulae (II) or (IV), wherein R5ais hydrogen or C1-C4 alkyl.

[0041] In some embodiments, Compounds of the Disclosure are compounds having Formulae (II) or (IV), wherein R5ais hydrogen or methyl.

[0042] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (II)-(IV), wherein R10and R11are independently hydrogen or C1-C9 alkyl.

[0043] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (II)-(IV), wherein R10and R11are hydrogen.

[0044] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (II)-(IV), wherein R10and R11are methyl.

[0045] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (II)-(IV), wherein R12ais hydrogen or C1-C9 alkyl.

[0046] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (II)-(IV), wherein R12ais hydrogen.

[0047] In some embodiments, Compounds of the Disclosure are compounds having Formula (V):or a salt, solvate, or stereoisomer thereof, wherein:R1, R2, R3, and R4are as defined in connection with Formula (I); and R10, R11, R12a, and R12bare as defined in connection with Formula (II).

[0048] In some embodiments, Compounds of the Disclosure are compounds havingFormula (VI):or a salt, solvate, or stereoisomer thereof, wherein:R1, R2, R3, and R4are as defined in connection with Formula (I); andR10, R11, R12a, and R12bare as defined in connection with Formula (II).

[0049] In some embodiments, Compounds of the Disclosure are compounds having Formula (VII):(VII), or a salt, solvate, or stereoisomer thereof, wherein:R1, R2, R3, and R4are as defined in connection with Formula (I); and R10, R11, R12a, and R12bare as defined in connection with Formula (II).

[0050] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (V)-(VII), wherein R10and R11are independently hydrogen or C1-C9 alkyl.

[0051] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (V)-(VII), wherein R10and R11are hydrogen.

[0052] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (V)-(VII), wherein R12aand R12bare independently hydrogen or C1-C9 alkyl.

[0053] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (V)-(VII), wherein R12aand R12bare hydrogen.

[0054] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (V)-(VII), wherein R10, R11, R12a, and R12bare hydrogen.

[0055] In some embodiments, Compounds of the Disclosure are compounds having Formula (VIII):(VIII), or a salt, solvate, or stereoisomer thereof, wherein:R1, R2, R3, R4, X5, and R6aare as defined in connection with Formula (I);= is a single or a double bond, with the proviso that when = is a double bond, then R6aand R13are absent; andR13and R14are selected from the group consisting of hydrogen and C1-C4 alkyl.

[0056] In some embodiments, Compounds of the Disclosure are compounds having Formula (IX):(IX), or a salt, solvate, or stereoisomer thereof, wherein:R1, R2, R3, R4, and R6aare as defined in connection with Formula (I);= is a single or a double bond; andR13and R14are as defined in connection with Formula (VIII), with the proviso that when = is a double bond, then R6aand R13are absent.

[0057] In some embodiments, Compounds of the Disclosure are compounds havingFormula (IX), wherein if = is a double bond, R14is methyl, and R2, R3, and R4are hydrogen, then R1is not:

[0058] In some embodiments, Compounds of the Disclosure are compounds having Formula (IX), wherein the compound is not:

[0059] In some embodiments, Compounds of the Disclosure are compounds having Formula (X):or a salt, solvate, or stereoisomer thereof, wherein:R1, R2, R3, R4, and R6aare as defined in connection with Formula (I);= is a single or a double bond; andR13and R14are as defined in connection with Formula (VIII), with the proviso that when = is a double bond, then R6aand R13are absent.

[0060] In some embodiments, Compounds of the Disclosure are compounds having Formula (X), wherein if = is a double bond, R14is methyl, and R2, R3, and R4are hydrogen, then R1is not:

[0061] In some embodiments, Compounds of the Disclosure are compounds having Formula (X), wherein the compound is not:

[0062] In some embodiments, Compounds of the Disclosure are compounds having Formula (XI):or a salt, solvate, or stereoisomer thereof, wherein:R1, R2, R3, R4, and R6aare as defined in connection with Formula (I); = is a single or a double bond; andR13and R14are as defined in connection with Formula (VIII), with the proviso that when = is a double bond, then R6aand R13are absent.

[0063] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (VIII)-(XI), wherein = is a double bond.

[0064] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (VIII)-(XI), wherein = is a single bond.

[0065] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (VIII)-(XI), wherein R6ais hydrogen or methyl.

[0066] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (VIII)-(XI), wherein R6ais hydrogen.

[0067] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (VIII)-(XI), wherein R13and R14are independently hydrogen or C1-C4 alkyl.

[0068] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (VIII)-(XI), wherein R13and R14are independently hydrogen or methyl.

[0069] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (VIII)-(XI), wherein R14is methyl.

[0070] In some embodiments, Compounds of the Disclosure are compounds having Formula (XII):(XII), or a salt, solvate, or stereoisomer thereof, wherein:R1, R2, R3, R4, X5, and R6aare as defined in connection with Formula (I);= is a single or a double bond, with the proviso that when = is a double bond, then R11and R12bare absent;R10is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, optionally substituted phenyl, -C(=O)OR7, -C(=O)NR7R8, -C(=O)SR7, -CH2OR7,-CH2OC(=O)R7, andR11is absent or is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl; orR10and R11taken together with the carbon atom to which they are attached form a C3-C12 cycloalkyl;R12ais selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl; andR12bis absent or is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl.

[0071] In some embodiments, Compounds of the Disclosure are compounds having Formula (XII), wherein X5is -CR5aR5b-.

[0072] In some embodiments, Compounds of the Disclosure are compounds having Formula (XII), wherein R5ais hydrogen or methyl.

[0073] In some embodiments, Compounds of the Disclosure are compounds havingFormula (XII), wherein R5bis hydrogen, C1-C9 alkyl, or optionally substituted phenyl

[0074] In some embodiments, Compounds of the Disclosure are compounds havingFormula (XII), wherein R10is hydrogen, C1-C9 alkyl, or optionally substituted phenyl

[0075] In some embodiments, Compounds of the Disclosure are compounds having Formula (XII), wherein R6ais hydrogen or methyl.

[0076] In some embodiments, Compounds of the Disclosure are compounds having Formula (XII), wherein = is a single bond.

[0077] In some embodiments, Compounds of the Disclosure are compounds having Formula (XII), wherein = is a double bond.

[0078] In some embodiments, Compounds of the Disclosure are compounds having Formula (XII), wherein R11is hydrogen or C1-C9 alkyl.

[0079] In some embodiments, Compounds of the Disclosure are compounds having Formula (XII), wherein R12bis hydrogen or C1-C9 alkyl.

[0080] In some embodiments, Compounds of the Disclosure are compounds having Formula (XIII):or a salt, solvate, or stereoisomer thereof, wherein:R1, R2, R3, R4, X5, and R6aare as defined in connection with Formula (I); each = is independently a single or a double bond; when X5is -CR5aR5b- or -NR5a-, then the = attached to X5is a single or a double bond, and when X5is -O- or -S-, then the == attached to X5is a single bond, with the provisos that when the = attached to X5is a double bond, then R12bis absent, and when the = attached to N is a double bond, then R11is absent;R10is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, optionally substituted phenyl, -C(=O)OR7, -C(=O)NR7R8, -C(=O)SR7, -CH2OR7, - CH2OC(=O)R7, andR11is absent or is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl; orR10and R11taken together with the carbon atom to which they are attached form a C3-C12 cycloalkyl;R12ais absent or is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, optionally substituted phenyl, -C(=O)OR7, -C(=O)NR7R8, -C(=O)SR7, -CH2OR7, - CH2OC(=O)R7, andR12bis selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl; orR12aand R12btaken together with the carbon atom to which they are attached form a C3-C12 cycloalkyl;R13ais selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl; andR13bis selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl.

[0081] In some embodiments, Compounds of the Disclosure are compounds having Formula (XIV):or a salt, solvate, or stereoisomer thereof, wherein:R1, R2, R3, R4, R6a, R10, R12a, R12b, R13a, and R13bare as defined in connection with Formula (XIII).

[0082] In some embodiments, Compounds of the Disclosure are compounds having Formula (XV):or a salt, solvate, or stereoisomer thereof, wherein:R1, R2, R3, R4, R6a, R10, R11, R12a, R13a, and R13bare as defined in connection with Formula (XIII).

[0083] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (XIII)-(XV), wherein R6ais hydrogen or methyl.

[0084] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (XIII)-(XV), wherein R6ais hydrogen.

[0085] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (XIII)-(XV), wherein R10is hydrogen or C1-C9 alkyl.

[0086] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (XIII)-(XV), wherein R10is methyl.

[0087] In some embodiments, Compounds of the Disclosure are compounds having Formula (XIII) or (XV), wherein R11is hydrogen or C1-C9 alkyl.

[0088] In some embodiments, Compounds of the Disclosure are compounds having Formula (XIII) or (XV), wherein R11is methyl.

[0089] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (XIII)-(XV), wherein R12ais hydrogen or C1-C9 alkyl.

[0090] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (XIII)-(XV), wherein R12ais methyl.

[0091] In some embodiments, Compounds of the Disclosure are compounds having Formula (XIII) or (XIV), wherein R12bis hydrogen or C1-C9 alkyl.

[0092] In some embodiments, Compounds of the Disclosure are compounds having Formula (XIII) or (XIV), wherein R12bis methyl.

[0093] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (XIII)-(XV), wherein R13ais hydrogen or C1-C9 alkyl.

[0094] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (XIII)-(XV), wherein R13ais hydrogen.

[0095] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (XIII)-(XV), wherein R13bis hydrogen or C1-C9 alkyl.

[0096] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (XIII)-(XV), wherein R13bis hydrogen.

[0097] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I)-(XV), wherein R1is C1-C12 alkyl.

[0098] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I)-(XV), wherein R1is methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, isopentyl, neo-pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, or dodecyl.

[0099] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I)-(XV), wherein R1is:

[0100] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein:R5is selected from the group consisting of hydrogen, optionally substituted C1-C12 alkyl, -CHR5cR5d, C3-C6 cycloalkyl, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl; andR6is selected from the group consisting of optionally substituted C1-C12 alkyl, -CHR6bR6c, C3-C6 cycloalkyl, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl.

[0101] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein Rlais hydrogen or methyl.

[0102] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein Rlais hydrogen.

[0103] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein R1is C1-C12 alkyl.

[0104] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein R1is -C(=O)R7.

[0105] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein R1is -C(=O)R7and R7is C1-C9 alkyl.

[0106] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein R1is -C(=O)C(CH3)3.

[0107] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein R1is methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, isopentyl, neo-pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, or dodecyl.

[0108] In some embodiments, Compounds of the Disclosure are compounds Formula (I), wherein R1is:

[0109] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein X5is -CR5aR5b-.

[0110] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein R5aand R5bare hydrogen.

[0111] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein R5aand R5bare C1-C4 alkyl.

[0112] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein X5is -NR5a-.

[0113] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein R5ais hydrogen or methyl.

[0114] In some embodiments, Compounds of the Disclosure are compounds havingFormula (I), wherein R5ais hydrogen.

[0115] In some embodiments, Compounds of the Disclosure are compounds havingFormula (I), wherein X5is -O-.

[0116] In some embodiments, Compounds of the Disclosure are compounds havingFormula (I), wherein R5is C1-C12 alkyl.

[0117] In some embodiments, Compounds of the Disclosure are compounds havingFormula (I), wherein R5is methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, isopentyl, neo-pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, or dodecyl.

[0118] In some embodiments, Compounds of the Disclosure are compounds Formula (I), wherein R5is:

[0119] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein R5is hydrogen.

[0120] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein R6is C1-C12 alkyl.

[0121] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein R6is methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, isopentyl, neo-pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, or dodecyl.

[0122] In some embodiments, Compounds of the Disclosure are compounds Formula (I), wherein R6is:

[0123] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein R6ais hydrogen or methyl.

[0124] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein R6ais hydrogen.

[0125] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I)-(XV), wherein R2, R3, and R4are independently hydrogen or C1-C9 alkyl.

[0126] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I)-(XV), wherein R2, R3, and R4are independently hydrogen or methyl.

[0127] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I)-(XV), wherein R4is methyl.

[0128] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I)-(XV), wherein R2and R3are hydrogen.

[0129] 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

[0130] 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.

[0131] Compounds of the Disclosure can be prepared by a two-step process comprising i) reacting a 1,3-diaminobenzene with one equivalent of a ketone, e.g., acetone, methyl isobutyl ketone, or methyl isoamyl ketone, or an aldehyde such as isobutyraldehyde, under reductive conditions, e.g., in the presence of hydrogen and a metal catalyst, e.g., platinum or palladium, or using hydride chemistry such as sodium borohydride, sodium triacetoxyborohydride, or sodium cyanoborohydride; and ii) reacting the l-alkylamino-3- aminobenzene product of step i) with a ketone or acetal, e.g., acetone, 2,2’ - dimethylpropane, or mesityl oxide, in the presence of an acid, base, or elemental halogen catalyst, e.g., hydrochloric acid, zinc(II) tritiate, lithium carbonate, or elemental iodine as shown in Scheme 1.Scheme 1H2

[0132] Compounds of the Disclosure can also be prepared by a two-step process comprising i) reacting a 3 -nitroaniline with a ketone or aldehyde, e.g., formaldehyde, and an olefin, e.g., alpha-methylstyrene, in the presence of an acid, e.g., trifluoroacetic acid; and ii) reacting the product of step i) with a ketone, e.g., acetone, methyl isobutyl ketone, or methyl isoamyl ketone, or an aldehyde such as isobutyraldehyde, under reductive conditions, e.g., in the presence of hydrogen and a metal catalyst, e.g., platinum or palladium, or using hydride chemistry such as sodium borohydride, sodium triacetoxyborohydride, or sodium cyanoborohydride, as shown in Scheme 2.Scheme 2

[0133] Compounds of the Disclosure can also be prepared by further reduction of compounds synthesized using Scheme 1, as shown in Scheme 3. Reduction may be carried out using any methods known in the art, such as exposure to hydrogen over a palladium on carbon (Pd / C) catalyst.Scheme 3

[0134] Compounds of the Disclosure can also be prepared by a two-step process comprising i) reacting a 4-halo-l,2-diaminobenzene with a ketone or aldehyde, e.g., acetone, in the presence of an acid catalyst, e.g., zirconyl chloride octahydrate, and ii) reacting the product of step i) with an aniline, e.g., in a Buchwald-Hartwig coupling, as shown in Scheme 4.Scheme 4X = Cl, Br, I

[0135] The present disclosure also provides a composition comprising:(a) a compound of Formula (XIV), or a salt or solvate thereof; and(b) a compound of Formula (XV), or a salt or solvate thereof.

[0136] In some embodiments, the compound of Formula (XIV) and the compound of Formula (XV) are constitutional isomers of each other.

[0137] In some embodiments, the compound of Formula (XIV) is:or a salt or solvate thereof, and the compound of Formula (XV) is:or a salt or solvate thereof.Definitions

[0138] 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, thealkyl is a C1-C3 alkyl. Non-limiting exemplary C1-C12 alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, ec-butyl, / e / 7-butyl, zso-butyl, 3-pentyl, hexyl, heptyl, octyl, nonyl, and decyl.

[0139] 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.

[0140] The term "halo" or "halogen" as used herein by itself or as part of another group refers to -Cl, -F, -Br, or -I.

[0141] The term "nitro" as used herein by itself or as part of another group refers to -NO2.

[0142] The term "cyano" as used herein by itself or as part of another group refers to -CN.

[0143] The term "hydroxy" as herein used by itself or as part of another group refers to -OH.

[0144] 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.

[0145] In one embodiment, the amino is -NH2.

[0146] 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.

[0147] 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.

[0148] 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.

[0149] 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 fluorineatoms. In another embodiment, the alkyl is a Ci-Ce alkyl and the resulting haloalkyl is referred to as a "Ci-Ce haloalkyl." In another embodiment, the alkyl is a C1-C4 alkyl and the resulting haloalkyl is referred to as a "C1-C4 haloalkyl." In another embodiment, the alkyl group is a Ci or C2 alkyl. Non-limiting exemplary haloalkyl groups include 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.

[0150] 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.

[0151] 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.

[0152] The term "cycloalkyl" as used herein by itself or as part of another group refers to saturated and partially unsaturated, e.g., containing one or two double bonds, monocyclic, bicyclic, or tricyclic aliphatic hydrocarbons containing three to twelve carbon atoms, i.e., a C3-C12 cycloalkyl, or the number of carbons designated, e.g., a C3-C6 cycloalkyl such a cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. In one embodiment, the cycloalkyl is bicyclic, i.e., it has two rings. In another embodiment, the cycloalkyl is monocyclic, i.e., it has one ring. In another embodiment, the cycloalkyl is a C3-C8 cycloalkyl. In another embodiment, the cycloalkyl is a C3-C6 cycloalkyl. In another embodiment, the cycloalkyl is a Cs cycloalkyl, i.e., cyclopentyl. In another embodiment, the cycloalkyl is a Ce cycloalkyl, i.e., cyclohexyl. Non-limiting exemplary C3-C12 cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, norbomyl, decalin, adamantyl, cyclohexenyl, and spiro[3.3]heptane.

[0153] 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.

[0154] The term "heterocyclo" or "heterocyclyl" as used herein by itself or as part of another group refers to saturated and partially unsaturated, e.g., containing one or two double bonds, monocyclic, bicyclic, or tricyclic groups containing three to eighteen ring members, i.e., a 3- to 18-membered heterocyclo, comprising one, two, three, or four heteroatoms. Each heteroatom is independently oxygen, sulfur, or nitrogen. Each sulfur atom may be independently oxidized to give a sulfoxide, i.e., S(=O), or sulfone, i.e., S(=O)2. The term heterocyclo includes groups wherein one or more -CH2- groups is replaced with one or more -C(=O)- groups, including cyclic ureido groups such as imidazolidinyl-2-one, cyclic amide groups such as pyrrolidin-2-one or piperidin-2-one, and cyclic carbamate groups such as oxazolidinyl-2-one. The term heterocyclo also includes groups having fused optionally substituted aryl or optionally substituted heteroaryl groups such as indoline, indolin-2-one, 2,3-dihydro-lH-pyrrolo[2,3-c]pyridine, 2,3,4,5-tetrahydro-lH-benzo[d]azepine, or l,3,4,5-tetrahydro-2H-benzo[d]azepin-2-one. In some embodiments, heterocyclo is a 6-membered ring comprising one nitrogen atom. The heterocyclo may be fused to the rest of the molecule to form a bicyclic group, e.g., 1,2-dihydroquinoline or 1,2,3,4-tetrahydroquinoline.

[0155] The term "optionally substituted heterocyclo" or "optionally substituted heterocyclyl" as used herein by itself or part of another group refers to a heterocyclo group that is either unsubstituted or substituted with one to four substituents, wheren the substituents are each independently halo, nitro, cyano, hydroxyl, amino, (e.g., -NH2, alkylamino, or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl, or cycloalkyl.

[0156] 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 anotherembodiment, 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 / / -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.

[0157] 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.

[0158] 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).

[0159] The term "chiral center" or "asymmetric carbon atom" refers to a carbon atom to which four different groups are attached.

[0160] 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.

[0161] The term "racemic" refers to a mixture of equal parts of enantiomers and which mixture is optically inactive.

[0162] 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.

[0163] 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.

[0164] 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.

[0165] 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.

[0166] Salts and solvates, e.g., hydrates, of the Compounds of the Disclosure can also be used in the methods disclosed herein.

[0167] 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.

[0168] 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.

[0169] One type of solvate is a hydrate. A "hydrate" relates to a particular subgroup of solvates where the solvent molecule is water. Preparation of solvates is known in the art. See, for example, M. Caira et al, J. Pharmaceut. Sci., 93(3 / 601-611 (2004), which describes the preparation of solvates of fluconazole with ethyl acetate and with water. Similar preparation of solvates, hemisolvates, hydrates, and the like are described by van Tender et al., AAPS Pharm. Sci. Tech., 5(7 / Article 12 (2004), and A.L. Bingham et al., Chem. Commun. 603-604 (2001). A typical, non-limiting, process of preparing a solvate would involve dissolving a Compound of the Disclosure in a desired solvent (organic, water, or a mixture thereof) at temperatures above 20°C to about 25°C, thencooling 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.

[0170] 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.

[0171] 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).

[0172] 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.

[0173] 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 a blend 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 1kg of the compound and 1 kg of carbon black is 50 wt / wt % (1 kg / 2 kg = 0.20 x 100 = 50 wt / wt %). The wt / wt % of a Compound of the Disclosure in a composition comprising 1 kg of the compound, 1 kg natural rubber, 2 kg of synthetic rubber, and 1 kg of carbon black is 20 wt / wt % (1 kg / 5 kg = 0.20 x 100 = 20 wt / wt %). The wt / wt % of natural rubber in a blend of one or more elastomers comprising 20 kg natural rubber and 30 kg synthetic rubber is 40 wt / wt % (20 kg / 50 kg = 0.40 x 100 = 40 wt / wt %).

[0174] 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.

[0175] 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 a combination 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.

[0176] 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

[0177] 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.

[0178] In some embodiments, a Composition of the Disclosure comprises from about 15 wt / wt % to about 85 wt / wt % of a Compound of the Disclosure. In some embodiments, the composition comprises from about 1 wt / wt % to about 5 wt / wt %, fromabout 1 wt / wt % to about 15 wt / wt %, from about 1 wt / wt % to about 25 wt / wt %, from about 1 wt / wt % to about 35 wt / wt %, from about 1 wt / wt % to about 45 wt / wt %, from about 1 wt / wt % to about 55 wt / wt %, from about 1 wt / wt % to about 65 wt / wt %, from about 1 wt / wt % to about 75 wt / wt %, from about 1 wt / wt % to about 85 wt / wt %, from about 1 wt / wt % to about 95 wt / wt %, from about 5 wt / wt % to about 15 wt / wt %, from about 5 wt / wt % to about 25 wt / wt %, from about 5 wt / wt % to about 35 wt / wt %, from about 5 wt / wt % to about 45 wt / wt %, from about 5 wt / wt % to about 55 wt / wt %, from about 5 wt / wt % to about 65 wt / wt %, from about 5 wt / wt % to about 75 wt / wt %, from about 5 wt / wt % to about 85 wt / wt %, from about 5 wt / wt % to about 95 wt / wt %, from about 15 wt / wt % to about 25 wt / wt %, from about 15 wt / wt % to about 35 wt / wt %, from about 15 wt / wt % to about 45 wt / wt %, from about 15 wt / wt % to about 55 wt / wt %, from about 15 wt / wt % to about 65 wt / wt %, from about 15 wt / wt % to about 75 wt / wt %, from about 15 wt / wt % to about 95 wt / wt %, from about 25 wt / wt % to about 35 wt / wt %, from about 25 wt / wt % to about 45 wt / wt %, from about 25 wt / wt % to about 55 wt / wt %, from about 25 wt / wt % to about 65 wt / wt %, from about 25 wt / wt % to about 75 wt / wt %, from about 25 wt / wt % to about 85 wt / wt %, from about 25 wt / wt % to about 95 wt / wt %, from about 35 wt / wt % to about 45 wt / wt %, from about 35 wt / wt % to about 55 wt / wt %, from about 35 wt / wt % to about 65 wt / wt %, from about 35 wt / wt % to about 75 wt / wt %, from about 35 wt / wt % to about 85 wt / wt %, from about 35 wt / wt % to about 95 wt / wt %, from about 45 wt / wt % to about 55 wt / wt %, from about 45 wt / wt % to about 65 wt / wt %, from about 45 wt / wt % to about 75 wt / wt %, from about 45 wt / wt % to about 85 wt / wt %, from about 45 wt / wt % to about 95 wt / wt %, from about 55 wt / wt % to about 65 wt / wt %, from about 55 wt / wt % to about 75 wt / wt %, from about 55 wt / wt % to about 85 wt / wt %, from about 55 wt / wt % to about 95 wt / wt %, from about 65 wt / wt % to about 75 wt / wt %, from about 65 wt / wt % to about 85 wt / wt %, from about 65 wt / wt % to about 95 wt / wt %, from about 75 wt / wt % to about 85 wt / wt %, from about 75 wt / wt % to about 95 wt / wt %, or from about 85 wt / wt % to about 95 wt / wt % of a Compound of the Disclosure. In some embodiments, the composition comprises from about 0.1 wt / wt% to about 0.5 wt / wt%, from about 0.1 wt / wt% to about 1 wt / wt%, from about 0.1 wt / wt% to about 1.5 wt / wt%, from about 0.1 wt / wt% to about 2 wt / wt%, from about 0.1 wt / wt% to about 2.5 wt / wt%, from about 0.1 wt / wt% to about 3 wt / wt%, from about 0.1 wt / wt% to about 3.5 wt / wt%, from about 0.1 wt / wt% to about 4 wt / wt%, from about 0.1 wt / wt% to about 4.5 wt / wt%,from about 0.1 wt / wt% 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 9 wt / wt%, from about 2 wt / wt% to about 10 wt / wt%, from about 2.5 wt / wt% to about 3 wt / wt%, from about 2.5 wt / wt% to about 3.5 wt / wt%, from about 2.5 wt / wt% to about 4 wt / wt%, from about 2.5 wt / wt% to about 4.5 wt / wt%, from about 2.5 wt / wt% to about 5 wt / wt%, from about 2.5 wt / wt% to about 6 wt / wt%, from about 2.5 wt / wt% to about 7 wt / wt%, from about 2.5 wt / wt% to about 8 wt / wt%, from about 2.5 wt / wt% to about 9 wt / wt%, from about 2.5wt / 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.

[0179] In some embodiments, a Composition of the Disclosure comprises about 50 wt / wt % of a Compound of the Disclosure. In some embodiments, the composition comprises about 1 wt / wt %, about 5 wt / wt %, about 10 wt / wt %, about 15 wt / wt %, about 20 wt / wt %, about 25 wt / wt %, about 30 wt / wt %, about 35 wt / wt %, about 40 wt / wt %, about 45 wt / wt %, about 55 wt / wt %, about 60 wt / wt %, about 65 wt / wt %, about 70 wt / wt %, about 75 wt / wt %, about 80 wt / wt %, about 85 wt / wt %, about 90 wt / wt %, or about 95 wt / wt % of a Compound of the Disclosure. In some embodiments, the composition comprises about 0.1 wt / wt%, about 0.5 wt / wt%, about 1 wt / wt%, about 1.5 wt / wt%, about 2 wt / wt%, about 2.5 wt / wt%, about 3 wt / wt%, about 3.5 wt / wt%, about 4 wt / wt%, about4.5 wt / wt%, about 5 wt / wt%, about 5.5 wt / wt%, about 6 wt / wt%, about 6.5 wt / wt%, about 7 wt / wt%, about 7.5 wt / wt%, about 8 wt / wt%, about 8.5 wt / wt%, about 9 wt / wt%, or about 10 wt / wt% of a Compound of the Disclosure.

[0180] In another embodiment, a Composition of the Disclosure comprises a Compound of the Disclosure and one or more elastomers.

[0181] 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.

[0182] 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 canbe obtained from "non-Hevea" sources. In some embodiments, the alternative rubber plant is Parthenium argentatum (guayule) or Taraxacum kok-saghyz (Russian dandelion).

[0183] 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.

[0184] In some embodiments, a Composition of the Disclosure comprises from about15 wt / wt % to about 100 wt / wt % of one or more elastomers. In some embodiments, the composition comprises from about 1 wt / wt % to about 5 wt / wt %, from about 1 wt / wt % to about 15 wt / wt %, from about 1 wt / wt % to about 25 wt / wt %, from about 1 wt / wt % to about 35 wt / wt %, from about 1 wt / wt % to about 45 wt / wt %, from about 1 wt / wt % to about 55 wt / wt %, from about 1 wt / wt % to about 65 wt / wt %, from about 1 wt / wt % to about 75 wt / wt %, from about 1 wt / wt % to about 85 wt / wt %, from about 1 wt / wt % to about 95 wt / wt %, from about 1 wt / wt % to about 100 wt / wt %, from about 5 wt / wt % to about 15 wt / wt %, from about 5 wt / wt % to about 25 wt / wt %, from about 5 wt / wt % to about 35 wt / wt %, from about 5 wt / wt % to about 45 wt / wt %, from about 5 wt / wt % to about 55 wt / wt %, from about 5 wt / wt % to about 65 wt / wt %, from about 5 wt / wt % to about 75 wt / wt %, from about 5 wt / wt % to about 85 wt / wt %, from about 5 wt / wt % to about 95 wt / wt %, from about 5 wt / wt % to about 100 wt / wt %, from about 15 wt / wt % to about 25 wt / wt %, from about 15 wt / wt % to about 35 wt / wt %, from about 15 wt / wt % to about 45 wt / wt %, from about 15 wt / wt % to about 55 wt / wt %, from about 15 wt / wt % to about 65 wt / wt %, from about 15 wt / wt % to about 75 wt / wt %, from about 15 wt / wt % to about 95 wt / wt %, from about 15 wt / wt % to about 100 wt / wt %, from about 25 wt / wt % to about 35 wt / wt %, from about 25 wt / wt % to about 45 wt / wt %, from about 25 wt / wt % to about 55 wt / wt %, from about 25 wt / wt % to about 65 wt / wt %, from about 25 wt / wt % to about 75 wt / wt %, from about 25 wt / wt % to about 85 wt / wt %, from about 25 wt / wt % to about 95 wt / wt %, from about 25 wt / wt % to about 100 wt / wt %, from about 35 wt / wt % to about 45 wt / wt %, from about 35 wt / wt % to about 55 wt / wt %, from about 35 wt / wt % to about 65 wt / wt %, from about 35 wt / wt % to about 75 wt / wt %, from about 35 wt / wt % to about 85 wt / wt %, from about 35 wt / wt % to about 95 wt / wt %, from about 35 wt / wt % to about 100 wt / wt %, from about 45 wt / wt % to about 55 wt / wt %, from about 45 wt / wt % to about 65 wt / wt %, from about 45 wt / wt % to about 75 wt / wt %, from about 45 wt / wt % to about 85 wt / wt %, from about 45 wt / wt % to about 95 wt / wt %, from about 45wt / wt % to about 100 wt / wt %, from about 55 wt / wt % to about 65 wt / wt %, from about 55 wt / wt % to about 75 wt / wt %, from about 55 wt / wt % to about 85 wt / wt %, from about 55 wt / wt % to about 95 wt / wt %, from about 55 wt / wt % to about 100 wt / wt %, from about 65 wt / wt % to about 75 wt / wt %, from about 65 wt / wt % to about 85 wt / wt %, from about 65 wt / wt % to about 95 wt / wt %, from about 65 wt / wt % to about 100 wt / wt %, from about 75 wt / wt % to about 85 wt / wt %, from about 75 wt / wt % to about 95 wt / wt %, from about 75 wt / wt % to about 100 wt / wt %, from about 85 wt / wt % to about 95 wt / wt %, or from about 95 wt / wt % to about 100 wt / wt % of one or more elastomers.

[0185] In some embodiments, a Composition of the Disclosure comprises about 50 wt / wt % of one or more elastomers. In some embodiments, the composition comprises about 1 wt / wt %, about 5 wt / wt %, about 10 wt / wt %, about 15 wt / wt %, about 20 wt / wt %, about 25 wt / wt %, about 30 wt / wt %, about 35 wt / wt %, about 40 wt / wt %, about 45 wt / wt %, about 55 wt / wt %, about 60 wt / wt %, about 65 wt / wt %, about 70 wt / wt %, about 75 wt / wt %, about 80 wt / wt %, about 85 wt / wt %, about 90 wt / wt %, about 95 wt / wt %, or about 100 wt / wt% of one or more elastomers.

[0186] 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.

[0187] 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 phrto 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.

[0188] In some embodiments, a Composition of the Disclosure comprises about 3 phr of a Compound of the Disclosure. In some embodiments, the composition comprises about 0.01 phr, about 0.1 phr, about 0.5 phr, about 1 phr, about 2 phr, about 3 phr, about 4 phr, about 5 phr, about 7.5 phr, about 10 phr, or about 20 phr of a Compound of the Disclosure.

[0189] In some embodiments, a Composition of the Disclosure comprises a Compound of the Disclosure and one or more fillers.

[0190] 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.

[0191] In some embodiments, the filler is derived from natural sources. For example, silica may be derived from rice husks.

[0192] 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 % toabout 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 fillers.

[0193] 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.

[0194] In some embodiments, a Composition of the Disclosure comprises from about 30 phr to about 500 phr of one or more fillers. In some embodiments, the composition comprises from about 30 phr to about 50 phr, from about 30 phr to about 100 phr, from about 30 phr to about 150 phr, from about 30 phr to about 200 phr, from about 30 phr to about 250 phr, from about 30 phr to about 300 phr, from about 30 phr to about 350 phr,from about 30 phr to about 400 phr, from about 30 phr to about 450 phr, from about 30 phr to about 500 phr, from about 50 phr to about 100 phr, from about 50 phr to about 150 phr, from about 50 phr to about 200 phr, from about 50 phr to about 250 phr, from about 50 phr to about 300 phr, from about 50 phr to about 350 phr, from about 50 phr to about 400 phr, from about 50 phr to about 450 phr, from about 50 phr to about 500 phr, from about 100 phr to about 150 phr, from about 100 phr to about 200 phr, from about 100 phr to about 250 phr, from about 100 phr to about 300 phr, from about 100 phr to about 350 phr, from about 100 phr to about 400 phr, from about 100 phr to about 450 phr, from about 100 phr to about 500 phr, from about 150 phr to about 200 phr, from about 150 phr to about 250 phr, from about 150 phr to about 300 phr, from about 150 phr to about 350 phr, from about 150 phr to about 400 phr, from about 150 phr to about 450 phr, from about 150 phr to 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.

[0195] 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.

[0196] 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.

[0197] 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. Inparticular, 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.

[0198] 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.

[0199] The term "accelerator" as used herein refers to any substance that increases the kinetics of vulcanization. In some embodiments, accelerators enable vulcanization to be performed at lower temperatures and / or to use the vulcanization agent, e.g., sulfur, more efficiently. Non-limiting examples of accelerators include guanidines, thiazoles, sulfenamides, thiurams, dithiocarbamates, xanthates, and thiophosphates. Non-limiting examples of guanidines include diphenylguanidine (DPG). Non-limiting examples of thiazoles include 2-mercaptobenzothiazole (MBT), zinc 2-mercaptobenzothiazole (ZMBT), mercaptobenzothiazole disulfide (MBTS), and V- / ert-butyl-2-benzothi azole sulfenimide (TBSI). Non-limiting examples of sulfenamides include N- / c / 7-butyl-2- benzothiazylsulfenamide (TBBS), 7V-cyclohexylbenzothiazol-2-sulfenamide (CBS), dicyclohexyl-2-benzothiazolesulfenamide (DCBS), V-oxy di ethylene benzothiazolesulfenamide (OBTS), A -oxy di ethylenethiocarb amyl - / ' / '-oxy diethylene 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).

[0200] 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 chemical complexes 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.

[0201] 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 A- (cyclohexylthio)phthalimide (CTP), benzoic anhydride, salicylic anhydride, and phthalic anhydride.

[0202] In some embodiments, a Composition of the Disclosure comprises from about 15 wt / wt % to about 85 wt / wt % of one or more rubber chemicals. In some embodiments, the composition comprises from about 1 wt / wt % to about 5 wt / wt %, from about 1 wt / wt % to about 15 wt / wt %, from about 1 wt / wt % to about 25 wt / wt %, from about 1 wt / wt % to about 35 wt / wt %, from about 1 wt / wt % to about 45 wt / wt %, from about 1 wt / wt % to about 55 wt / wt %, from about 1 wt / wt % to about 65 wt / wt %, from about 1 wt / wt % to about 75 wt / wt %, from about 1 wt / wt % to about 85 wt / wt %, from about 1 wt / wt % to about 95 wt / wt %, from about 5 wt / wt % to about 15 wt / wt %, from about 5 wt / wt % to about 25 wt / wt %, from about 5 wt / wt % to about 35 wt / wt %, from about 5 wt / wt % toabout 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 rubber chemicals.

[0203] 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.

[0204] 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 about0.1 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.

[0205] 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.

[0206] 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.

[0207] 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 % toabout 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 plasticizers.

[0208] 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.

[0209] In some embodiments, a Composition of the Disclosure comprises from about 1 phr to about 20 phr of one or more plasticizers. In some embodiments, the composition comprises from about 0.1 phr to about 1 phr, from about 0.1 phr to about 5 phr, from about 0.1 phr to about 10 phr, from about 0.1 phr to about 15 phr, from about 0.1 phr to about 20 phr, from about 0.1 phr to about 25 phr, from about 0.1 phr to about 30 phr, from about 0.1 phr to about 35 phr, from about 0.1 phr to about 40 phr, from about 1 phr to about 5 phr, from about 1 phr to about 10 phr, from about 1 phr to about 15 phr, from about 1 phr to about 25 phr, from about 1 phr to about 30 phr, from about 1 phr to about 35 phr, from about 1 phr to about 40 phr, from about 5 phr to about 10 phr, from about 5 phr to about 15 phr, from about 5 phr to about 20 phr, from about 5 phr to about 25 phr, from about 5 phr to about 30 phr, from about 5 phr to about 35 phr, from about 5 phr to about 40 phr, from about 10 phr to about 15 phr, from about 10 phr to about 20 phr, from about 10 phr to about 25 phr, from about 10 phr to about 30 phr, from about 10 phr to about 35 phr, from about 10 phr to about 40 phr, from about 15 phr to about 20 phr, from about 15 phr to about 25 phr, from about 15 phr to about 30 phr, from about 15 phr to about 35 phr, from about 15 phr to about 40 phr, from about 20 phr to about 25 phr, from about 20 phr to about 30 phr, from about 20 phr to about 35 phr, from about 20 phr to about 40 phr, from about 25 phr 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.

[0210] 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.

[0211] In some embodiments, a Composition of the Disclosure further comprises one or more additional anti degradants that is (are) not a Compound of the Disclosure.

[0212] In some embodiments, the one of the additional antidegradants is an antioxidant. In some embodiments, the one of the additional anti degradants is an antiozonant. Nonlimiting examples of anti degradants include paraphenylenediamines (PPDs), trimethyldihydroquinolines (TMQs), phenolics, alkylated diphenylamines (DP As), diphenylamineketone condensates, and natural anti degradants. Non-limiting examples of PPDs include N1-(4-methyl pentan-2-yl )-N4-phenylbenzene- 1 ,4-diamine (6PPD), N-( 1 ,4-dimethylpentyl)-7V-phenyl-p-phenylenediamine (7PPD), 7V1-phenyl-7V4-(propan-2- yl)benzene-l,4-diamine (IPPD), 7V,7V-di-5ec-butyl- / ?-phenylenediamine (44PD), N,N'~ bis(l,3-dimethylbutyl)-p-phenylenediamine (66PD), 7V,7V-bis(l,4-dimethylpentyl)-p- phenylenediamine (77PD), and 7V-7V'-dioctyl- / ?-phenylenediamine (88PD). Non-limiting examples of TMQs include 2,2,4-trimethyl-l,2-dihydroquinoline and oligomers or polymers thereof.

[0213] 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 %, 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 %, fromabout 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.

[0214] 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.

[0215] In some embodiments, a Composition of the Disclosure comprises from about 1 to about 5 phr of one or more additional anti degradants. In some embodiments, the composition comprises from about 0.001 phr to about 0.01 phr, from about 0.001 phr to about 0.1 phr, from about 0.001 phr to about 1 phr, from about 0.001 phr to about 5 phr, from about 0.001 phr to about 7.5 phr, from about 0.001 phr to about 10 phr, from about 0.01 phr to about 0.1 phr, from about 0.01 phr to about 1 phr, from about 0.01 phr to about 5 phr, from about 0.01 phr to about 7.5 phr, from about 0.01 phr to about 10 phr, from about 0.1 phr to about 1 phr, from about 0.1 phr to about 5 phr, from about 0.1 phr to about 7.5 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.

[0216] 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.

[0217] 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 someembodiments, the carrier has a high surface area. In some embodiments, the carrier comprises particles with diameters of less than 500 microns.

[0218] 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.

[0219] 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.

[0220] 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.

[0221] 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.

[0222] The present disclosure also provides combustible fuel compositions comprising a combustible fuel and a Compound of the Disclosure. Non-limiting examples of combustible fuel include gasoline, diesel, kerosene, liquefied petroleum gas, synthetic fuel, and biodisesel.

[0223] 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.

[0224] In some embodiments, the present disclosure provides a composition recited in Table 2.Table 2

[0225] 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 30wt / 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.

[0226] 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

[0227] 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.

[0228] The present disclosure also provides vulcanized elastomeric articles prepared using a composition described herein.

[0229] 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.

[0230] 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.

[0231] 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.

[0232] In some embodiments, the vulcanized elastomeric article comprises about 0.1 phr to about 10 phr of the Compound of the Disclosure. For example, the vulcanized elastomeric article comprises about 0.1 phr, about 0.2 phr, about 0.3 phr, about 0.4 phr, about 0.5 phr, about 0.6 phr, about 0.7 phr, about 0.8 phr, about 0.9 phr, about 1 phr, about 2 phr, about 3 phr, about 4 phr, about 5 phr, about 6 phr, about 7 phr, about 8 phr, about 9 phr, or about 10 phr of the Compound of the Disclosure.

[0233] In some embodiments, the present disclosure provides a vulcanized elastomeric article, e.g., a tire, comprising the components in Table 3.Table 3Processes

[0234] 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.

[0235] 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 performedat 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.

[0236] In some embodiments, the vulcanizing is performed at an average temperature of about 150 °C. In some embodiments, the vulcanizing is performed at an average temperature of about 80 °C, about 100 °C, about 120 °C, about 140 °C, about 160 °C, about 180 °C, or about 200 °C.

[0237] 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

[0238] 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 2,2,4,8-tetramethyl-N-(4-methylpentan-2-yl)-l,2-dihydroquinolin-7-amine(Compound 1)Step 1

[0239] To a 300-mL Parr autoclave was loaded 2-methylbenzene- 1,3 -diamine (25.4 g; 208 mmol), isopropanol (200 mL), methyl isobutyl ketone (MIBK; 26 mL; 208 mmol), and 3% Pt / C sulfided from Johnson Matthey (approx. 373 mg wet). The reaction mixture was stirred and heated to 180 °C under 450 PSI Eb for about 6-7 hours. Upon cooling to room temperature (overnight; under N2 protection), the mixture post reaction was filtered through inline 0.2-micron frit. The clave was rinsed with ethyl acetate (200 mL) and the contents were filtered through the inline frit. The combined filtrates were stripped of volatiles under reduced pressure (rotary evaporator; water bath = 55 °C). The crude material was diluted with hexanes (16 mL). The obtained slurry was loaded into a 73 mm inner diameter column chromatography prepared with silica gel 60 and 30% ethyl acetate in hexanes (height of wet silica gel in column = 19 cm). The flask and column walls were carefully rinsed with hexanes (9-10 mL). The column was eluted with 30% ethyl acetate in hexanes. Each fraction coming out (80-100 mL) was analyzed by silica gel TLC (30% ethyl acetate in hexanes). The fractions showing a dot at Rf = 0.4 were collected, combined, and stripped of volatiles under reduced pressure (rotary evaporator; water bath = 50 °C). The material was dried on the rotary evaporator (55 °C; < 25 mbars) for about 1.5 hours to afford 19.2 g (45% with respect to 2-methylbenzene- 1,3 -diamine) of 2- methyl-Nl-(4-methylpentan-2-yl)benzene-l,3-diamine (Intermediate compound 1-1) as an oil. Intermediate 1-1 was characterized by HPLC-UV / MS. The purity was 97.3 area% as measured at 260 nm detection.Step 2Compound 1

[0240] To a 500-mL round bottom flask fitted with a stir-bar and a 60-mL pressure- equalized addition funnel was loaded Intermediate compound 1-1 (36.3 g; 176 mmol). The flask was put under N2 protection and magnetic stirring was started. Aqueous 37% HC1 (2.2 mL; 27 mmol HC1) was added. The mixture was heated with an oil bath set to 104 °C. Mesityl oxide (47.5 mL; 413 mmol) was placed in the addition funnel. Once the set temperature was attained, mesityl oxide was dropwise added over about 1.5 hours. After completion of the mesityl oxide addition, the reaction mixture was stirred and maintained at the same temperature for 30 minutes. Upon cooling to room temperature, sodium carbonate (6.01 g; 56.7 mmol) was added in one portion. The mixture was stirred for about 1.5 hours, allowed to stand overnight, then loaded into a 73 mm inner diameter column prepared with silica gel 60 and 10% ethyl acetate in hexanes (height of wet silica gel in column = 28 cm). The flask and column walls were rinsed with minute amounts of hexanes. The column was eluted with 10% ethyl acetate in hexanes. Each fraction coming out was analyzed by silica gel TLC (10% ethyl acetate in hexanes). The fractions showing a dot at Rf = 0.5 were collected, combined, and stripped of volatiles under reduced pressure (rotary evaporator; water bath = 50 °C). At that stage, the product was an orange liquid weighing 28.4 grams and was 76-77 area% pure as measured by HPLC-UV at 260 nm detection. The impure material was diluted with hexanes (13 mL). The obtained solution was loaded into a 73 mm inner diameter column prepared with silica gel 60 and 5% ethyl acetate in hexanes (height of silica gel = 16 cm). The flask and column walls were rinsed with minute amounts of hexanes. The column was eluted with 5% ethyl acetate in hexanes. Each fraction coming out was analyzed by silica gel TLC (5% ethyl acetate in hexanes). The fractions showing a dot at Rf = 0.3 were collected, combined, and stripped of volatiles under reduced pressure (rotary evaporator; water bath = 50 °C). Further drying on the rotary evaporator (water bath = 70 °C; < 3 mbars) for approx. 2hours afforded 24.0 g (47% yield with respect to Intermediate Compound 1-1) of 2, 2,4,8- tetramethyl-N-(4-methylpentan-2-yl)-l,2-dihydroquinolin-7-amine (Compound 1) as an orange liquid. The desired structure was authenticated by proton and carbon 13 APT NMR spectroscopy (DMSO-de), as shown in Figs. 1 and 2, respectively. LC-UV analysis showed 97.5% purity at 260 nm detection.EXAMPLE 2Synthesis of N-isopropyl-4,8-dimethyl-4-phenyl-l,2,3,4-tetrahydroquinolin-7-amine (Compound 2)Step 1

[0241] To a 1-L round bottom flask fitted with a reflux condenser was loaded 2-methyl- 3 -nitroaniline (20.1 g, 0.132 mol) and acetonitrile (250 mL). The mixture was stirred under nitrogen. To the obtained clear yellow solution was added trifluoroacetic acid (TFA, 10.72 mL, 0.140 mol), aqueous 37% formaldehyde solution (17.4 mL, 0.233 mol HCHO), and alpha-methylstyrene (30.7 mL, 0.236 mol) in that order. Upon addition of alpha-methylstyrene, the solution increased in temperature from 19 °C to 28 °C, and the color became reddish. The reaction mixture was stirred for 4 hours in an 85 °C oil bath. Aqueous 1.2 M sodium bicarbonate 250 mL was added to quench the TFA. The reaction was stirred until frothing ceased, and the mixture was transferred to a 2-L separatory funnel. The aqueous phase was discarded and to the organic layer was added 250 mL of IM sodium bisulfite. The mixture was shaken and the aqueous layer was discarded. The organic layer was then washed with 250 mL of brine, and dried over magnesium sulfate. The suspension was then filtered and evaporated to yield a dark orange oil (24.15 g). A 10 g portion of the dark oil was eluted through silica gel using 20% v / v ethyl acetate / hexanes, and the fractions containing product were collected and evaporated to give 4,8-dimethyl-7-nitro-4-phenyl-l,2,3,4-tetrahydroquinoline (Intermediate Compound 2-1) as a yellow oil (2.73 g). Intermediate compound 2-1 was characterized by13C APTNMR spectroscopy in DMSO-tL, as shown in Fig. 3. The material was used in Step 2 without further purification.Step 2

[0242] To a 300-mL Parr autoclave was loaded Intermediate Compound 2-1 (2.60 g, 9.21 mmol), 3% Pt / C sulfided from Johnson Matthey (0.0629 g wet), acetone (1.75 mL, 23.6 mmol), and isopropanol (140 mL). The reaction mixture was stirred and heated to 150 °C under 250 PSI EE for 6 hours. Upon cooling to room temperature, the solution was filtered through the inline 0.2-micron frit. The reactor was rinsed with an additional 50 mL of fresh isopropanol and the mixture was filtered through the inline 0.2-micron frit. The filtrates were combined and concentrated under reduced pressure at 50 °C to approx. 10 mL. The product was purified on a silica gel column using 20% v / v ethyl acetate / hexanes. Volatiles were evaporated under reduced pressure at 50 °C to give a viscous orange oil. Upon standing for 16 hours at ambient temperature the oil became a crystalline orange solid yielding 1.75 g of N-isopropyl-4,8-dimethyl-4-phenyl-l, 2,3,4- tetrahydroquinolin-7-amine (Compound 2) (97.1% purity by HPLC at 260 nm, 63% yield). MS (APCI+): m / z: [M+l] 295 amu. Compound 2 was characterized by13C APT NMR spectroscopy in CDCh, as shown in Fig. 4.EXAMPLE 3Synthesis of 2,2,4-trimethyl-N-phenyl-2,3-dihydro-lH-benzo[b][l,4]diazepin-8-amine and 2,2,4-trimethyl-N-phenyl-2,3-dihydro-lH-benzo[b][l,4]diazepin-7-amine (mixture of Compounds 19 and 20)Step 1

[0243] To a 250-mL round bottom flask fitted with a stir-bar was charged 4-bromo-l,2- diaminobenzene (14.5 g; 77.5 mmol). The flask was put under N2 protection and acetone (28.5 mL; 388 mmol) was added. Stirring was started (the substrate dissolved readily) and zirconyl chloride octahydrate (2.45 g; 7.6 mmol Zr4+cation) was added in several portions over 2-3 minutes (an insignificant exotherm ensured). The reaction mixture was stirred without external cooling or heating for 18h30 (overnight). The obtained dark slurry was loaded into a 73 mm inner diameter column prepared with silica gel 60 and 30% AcOEt in hexanes. The height of wet silica gel in the column was 12.5-13.0 cm. The flask and column walls were rinsed with minutes amounts of toluene. The column was eluted with 30% AcOEt in hexanes. Each fraction coming out was analyzed by silica gel TLC (30% AcOEt in hexanes). The fractions containing the dot at Rf = 0.2 were combined and stripped of volatiles under reduced pressure (rotary evaporator; water bath = 50 deg C). Further drying on the rotary evaporator (55 deg C; approx. 75 mbars) for 2 hours afforded 15.7 g of a light-brown oil. Carbon 13 APT NMR analysis (DMSO-de) displayed the presence of 2 regioisomers (mixture of Compound 3-1 and Compound 3 -II), as shown in Fig. 5. The purity was 88.4area% as measured by HPLC-UV at 260 nm detection (a single peak accounting for the 2 regioisomers Compounds 3-1 and Compound 3-II was observed). The material was used in Step 2 without further purification.Step 2

[0244] To a 250-mL round bottom flask fitted with a stir-bar and a reflux condenser was charged the mixture of compounds 3-1 and 3-II (4.95 g; 18.5 mmol total aryl-Br), anhydrous grade toluene (50 mL), and aniline (2.2 mL; 24.1 mmol). The mixture was stirred under N2 blanket. Once the substrate was fully dissolved, N2 was bubbled thought the solution for a few min. Dicyclohexyl(2',4',6'-triisopropyl-[l,l'-biphenyl]-2- yl)phosphane (0.365 g; 0.766 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.353 g; 0.385 mmol), and sodium tert-butoxide (2.50 g; 26.0 mmol) were sequentially added tothe flask. N2 was bubbled through the mixture for a few min one more time. The reaction mixture was heated (oil bath temperature set to 105 deg C) under N2 blanket for 5 hours. Upon cooling to room temperature (overnight), the mixture post-reaction was filtered under suction over Celite S. The cake was rinsed with toluene. The combined filtrates were stripped of volatiles under reduced pressure (rotary evaporator; water bath = 65 deg C). The obtained thick dark liquid was diluted with minute amounts of toluene and loaded into a 41 mm inner diameter column prepared with silica gel 60 and AcOEt. The height of wet silica gel in the column was 22-23 cm. The column was eluted with AcOEt, then with 10% isopropanol in AcOEt. Each fraction coming out was analyzed by silica gel TLC (AcOEt). The fractions containing the dot at Rf = 0.4 were combined and stripped of volatiles under reduced pressure (rotary evaporator; water bath = 55 deg C). Further drying on the rotary evaporator (water bath = 55 °C; < 25 mbars) until constant weight afforded 4.0 g of a brown glassy solid (mixture of Compound 19 and Compound 20; combined yield = 77% with respect to total aryl bromide). The desired structures were authenticated by carbon 13 APT NMR spectroscopy (DMSO-de), as shown in Fig. 6. LC- UV analysis showed 98.5% purity at 260 nm detection (a single peak accounting for the 2 regioisomers Compounds 19 and Compound 20 was observed).EXAMPLE 4Synthesis of N',N2,N4-trineopentylbenzene- l ,2,4-triamine (Compound 11)

[0245] This is a prophetic example. Concentrated sulfuric acid (15 mmol) is dropwise added at 0 °C to a suspension of 30 mmol of lithium aluminum hydride in 100 mL of argon saturated THF. After hydrogen gas evolution ceases, the resulting suspension is stirred for 1 h at ambient temperature. 1.0 mmol of l,2,4-tris(2,2- dimethylpropanamido)benzene (Seillan et al Eur. J. Org Chem 2008, 3113) is slowlyadded portion-wise. The resulting mixture is stirred for 3 days at ambient temperature. Degassed water is added at 0 °C to quench the aluminum hydrides. The solution is extracted 3x with diethyl ether and the combined extracts are dried over Mg2SO4. After filtration, solvent is removed in vacuo to afford compound 11.EXAMPLE 5Synthesis of N-isopropylbenzo[d]thiazol-5-amine (Compound 17)

[0246] To a stirred solution of benzo[d]thiazol-5-amine (50.0 g, 0.333 mol) in acetone (500 mL) was added acetic acid (250 mL) at RT, followed by the addition of NaCNBEE (62.5 g, 1.00 mol), portion-wise for 30 min. The resulting reaction contents were stirred for 30-40 min at room temperature. After completion of reaction (monitored by TLC), the reaction was quenched with ice-cold water and extracted with ethyl acetate (2 x 500 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated under vacuum to afford 82 g of crude. The crude was purified by silica gel column chromatography (100-200 mesh) eluting with 10-15% ethyl acetate in hexane to afford 37.5 g of compound 17 (>99% pure by HPLC 260 nm, Mass (m / z): 193.32 [M+H]+) as a light brown oil.

[0247] 1H NMR (400 MHz, DMSO-de): 5 9.18 (s, 1H), 7.74 (d, J= 8.8 Hz, 1H), 7.13 (d, J= 2.4 Hz, 1H), 6.84 (dd, J= 8.8, 2.4 Hz, 1H), 5.62 (d, J= 8.0 Hz, 1H), 3.66-3.57 (m, 1H), 1.17 (d, J= 6.4 Hz, 6H).

[0248] 13C NMR (100 MHz, DMSO-de): 5 155.63, 155.56, 147.91, 122.40, 120.36,115.31, 103.91, 43.76, 22.74.EXAMPLE 6Synthesis of di-tert-butyl 6-(isopropylamino)-2,3-dihydroquinoxaline-l,4-dicarboxylate hydrochloride (Compound 5)

[0249] To a stirred solution of 6-nitroquinoxaline (25.0 g, 0.142 mol) in water (375.0 mL, 15.0 vol) was added borane trimethylamine complex (10.4 g, 0.142 mol) at room temperature followed by the dropwise addition of trifluoroacetic acid (54.3 mL, 0.71 mol) over a period of 20-30 min. The resulting reaction contents were stirred at room temperature for 5h. After completion of reaction (monitored by TLC), the mixture was quenched with water, neutralized with 20% NaOH solution and extracted with ethyl acetate (2 x 250.0 mL). The organic layers were combined, dried over sodium sulphate, filtered and evaporated under vacuum to afford 28 g of crude. The crude was purified by silica gel column chromatography (100-200 mesh) eluting with 3-5% ethyl acetate in hexane to afford 19.0 g of 6-nitro-l,2,3,4-tetrahydroquinoxaline as brown solid. Step 2

[0250] To a stirred solution of 6-nitro-l,2,3,4-tetrahydroquinoxaline (19.0 g, 0.116 mol) in dichloromethane (190.0 mL, 10.0 vol) was added triethyl amine (116.2 mL, 0.812 mol) and 4-dimethylaminopyridine (1.4 g, 0.011 mol) at room temperature, followed by thedropwise addition of Boc anhydride (133.0 mL, 0.582 mol) over a period of 30-40 min. The resulting reaction mixture was stirred at room temperature for 6 h. After completion of reaction (monitored by TLC), the mixture was quenched with water (50 mL) and extracted with DCM (200.0 mL). The organic layer was separated, dried over sodium sulphate, filtered and evaporated under vacuum to afford residue, which was triturated with n-pentane (100 mL) to afford 37.0 g of crude di-tert-butyl 6-nitro-2,3- dihydroquinoxaline-l,4-dicarboxylate as off-white solid. The material was used without additional purification.Step 3Boc Boc

[0251] To a stirred solution of di-tert-butyl 6-nitro-2, 3 -dihydroquinoxaline- 1,4- dicarboxylate (37.0 g, 0.097 mol) in acetone (370 mL, 10.0 vol) was added 5% Pt / C (11.0 g, 30% w / w) in an autoclave. Then, hydrogen pressure was applied (40 kg) into the autoclave and the system was heated to 65-70°C, for 16 h. After completion of reaction (monitored by TLC), the reaction was cooled to RT, filtered through celite bed and washed with acetone (150 mL). The filtrate was evaporated to afford 38.0 g of crude compound, which was triturated in n-pentane to afford 34.0 g of di-tert-butyl 6- (isopropylamino)-2,3-dihydroquinoxaline-l,4-dicarboxylate as off-white solid. This material was used without further purification.Step 4

[0252] To a stirred solution of di-tert-butyl 6-(isopropylamino)-2,3-dihydroquinoxaline- 1,4-dicarboxylate (92.0 g, 0.235 mol) in 1,4-dioxane (460.0 mL, 5.0 vol) was added 4M HC1 in dioxane (276.0 mL, 3.0 vol) dropwise for 45-60 min at room temperature. The resulting reaction mixture was stirred for 16 h. After completion of reaction (monitored by TLC), the solid was filtered under nitrogen atmosphere to afford 70.0 g of di-tert-butyl 6-(isopropylamino)-2,3-dihydroquinoxaline-l,4-dicarboxylate as its HC1 salt. The material was suspended the crude compound in IP A, stirred for 1 h at room temperature,filtered and washed with IPA and dried the solid under vacuum at 42-48°C to afford 42.2 g of Compound 5 (>96% pure by HPLC 260 nm, Mass (m / z): 192.13 [M+H]+) as an off- white solid.

[0253] 1H NMR (400 MHz, DMSO ): 5 10.84 (br s, 2H), 7.04 (d, J= 8.4 Hz, 1H), 6.96(s, 1H), 6.83 (d, J= 7.2, 1H), 3.56-3.50 (m, 1H), 3.39-3.35 (m, 4H), 1.28 (d, J= 6.8 Hz, 6H).

[0254] 13C NMR (100 MHz, D2O): 5 132.55, 130.42, 124.22, 122.73, 116.04, 113.48,55.66, 39.53, 38.30, 18.01.EXAMPLE 7Synthesis of N-isopropyl-3,4-dihydro-2H-benzo[b][l,4]oxazin-6-amine (Compound 13)

[0255] To a stirred solution of 2-amino-4-nitrophenol (100.0 g, 0.649 mol) in dichloromethane (3.3 L) was added triethylamine (271.0 mL, 1.947 mol) at 0-5°C, followed by the addition of chloro acetyl chloride (79.9 g, 0.714 mol) dropwise at 0-5°C. The resulting reaction mixture was allowed to stir at room temperature for 18 h. After completion of reaction (monitored by TLC), DCM was added (1.0 L) into the reaction and washed with water. The organic layer was separated, dried over sodium sulfate, filtered and evaporated under vacuum to afford 90 g of crude which was further triturated with n-pentane to afford 6-nitro-2H-benzo[b][l,4]oxazin-3(4H)-one as pale-yellow solid.Step 2

[0256] To a stirred solution of 6-nitro-2H-benzo[b][l,4]oxazin-3(4H)-one (50.0 g, 0.257 mol) in THF (500 mL) was added borane THF (IM in THF) (1.0 L, 4.0 eq) dropwise at 50-55°C. The resulting reaction contents were stirred for 4-5 h at 50-55°C. After completion of reaction (monitored by TLC), the mixture was cooled to room temperature, quenched with 3N HC1 (500 mL) and extracted with dichloromethane (1.0 L). The organic layer was separated, dried over sodium sulfate, filtered and evaporated under vacuum to afford 45 g of 6-nitro-3,4-dihydro-2H-benzo[b][l,4]oxazine as red solid.Step 3

[0257] To a stirred solution of 6-nitro-3,4-dihydro-2H-benzo[b][l,4]oxazine (30.0 g, 0.16 mol) in acetone (300 mL) was added 5% Pt / C (7.5 g, 25% w / w) in an autoclave. Hydrogen pressure was added (40 kg) into the autoclave, the system was heated to 65- 70°C and the reaction was stirred for 17 h. After completion of reaction (monitored by TLC), the mixture was cooled to RT, filtered through a celite bed and washed with methanol (200 mL). The collected filtrate was evaporated to give 29.0 g of crude, which was further purified by silica-gel (100-200 mesh) column chromatography eluting with 20-25% ethyl acetate in hexane to afford 18 g of compound 13 (>95% pure by HPLC 260 nm, Mass (m / z): 193.3 [M+H]+) as brown oil.

[0258] 1H NMR (400 MHz, DMSO-t / e): 5 6.36 (d, J= 8.8 Hz, 1H), 5.81 (s, 1H), 5.73 (dd, J= 8.4, 2.8 Hz, 1H), 5.44 (s, 1H), 4.50 (s, 1H), 3.97 (t, J= 4.8 Hz, 2H), 3.35-3.32 (m, 1H), 3.21-3.18 (m, 2H), 1.06 (d, J= 6.4 Hz, 6H).

[0259] 13C NMR (100 MHz, DMSO ): 5 143.30, 135.39, 135.06, 116.58, 102.60,100.05, 64.80, 44.20, 40.91, 23.17.EXAMPLE 8Synthesis of 2-(tert-butyl)-N-neopentyl-lH-benzo[d]imidazol-5-amine (Compound 21)Step 1

[0260] To a stirred solution of 4-nitrobenzene-l,2-diamine (70.0 g, 0.457 mol) in dimethyl acetamide (700.0 mL) was added sodium bisulfite (46.8 g, 0.457 mol) at 0-5°C, followed by the addition of freshly prepared pivalaldehyde (49.0 mL, 0.457 mol) solution in dimethyl acetamide (210.0 mL) dropwise over a period of 30-40 min. The resulting reaction mixture was heated to 95-100°C and stirred for 4 h. After completion of reaction (monitored by TLC), the mixture was quenched with chilled water (1.0 L) and extracted with ethyl acetate (1.0 L). The organic layer was separated, dried over sodium sulfate, filtered and evaporated under vacuum to afford 96 g of crude which was further purified by silica-gel (100-200 mesh) column chromatography eluting with 20-25% ethyl acetate in hexane to afford 45 g of 2-(tert-butyl)-5-nitro-lH-benzo[d]imidazole as light pink solid.Step 2

[0261] To a stirred solution of 2-(tert-butyl)-5-nitro-lH-benzo[d]imidazole (45.0 g, 0.205 mol) in methanol (450 mL) was added pivalaldehyde (45.3 mL, 0.410 mol) followed by the addition of 5% Pt / C (22.5 g, 25% w / w) in an autoclave. Hydrogen pressure was added (40 kg) into the autoclave and heated to 65-70°C, where the reaction was stirred for 17 h. After completion of reaction (monitored by TLC), the mixture was cooled to room temperature, filtered through celite bed and washed with methanol (200 mL). The filtrate was evaporated under reduced pressure to afford a crude, which was further purified by silica-gel (100-200 mesh) column chromatography eluting with 25-30% ethyl acetate in hexane to afford 43.0 g of compound 21 (>99 % pure by HPLC 260 nm, Mass (m / z): 260.3 [M+H]+) as an off-white solid.

[0262] 1H NMR (400 MHz, DMSO-t / e): 5 11.49 (s, 1H), 7.16-7.14 (m, 1H), 6.56 (d, J= 7.2 Hz, 2H), 5.09 (s, 1H), 2.80 (d, J= 4.8 Hz, 2H), 1.34 (s, 9H), 0.96 (s, 9H).

[0263] 13C NMR (100 MHz, CDCh): 5 160.92, 145.65, 138.34, 132.72, 116.50, 110.78,95.45, 57.04, 33.51, 31.85, 29.71, 27.75.EXAMPLE 9Synthesis of N-(3,4-bis(neopentylamino)phenyl)pivalamide (Compound 22)Step 1

[0264] To a stirred solution of 4-nitrobenzene-l,2-diamine (25.0 g, 0.163 mol) in acetic acid (250.0 mL) was added pivalaldehyde (108.0 mL, 0.980 mol) at room temperature. Then the system was cooled to 0-5°C and NaBHsCN (51.4 g, 0.816 mol) was addedportion wise for 15-20 min. The resulting reaction contents were warmed to room temperature and stirred for 2 h. After completion of reaction (monitored by TLC), the mixture was quenched with ice-cold water and extracted with ethyl acetate (2 x 250 mL). The organic layers were combined and washed with sat. NaHCCh solution (250 mL). The organic layer was separated, dried over sodium sulphate, filtered and evaporated under vacuum to afford 40 g of crude. The obtained crude was purified by silica gel column chromatography (100-200 mesh) eluting with 2-4% ethyl acetate in hexane to afford Nl,N2-dineopentyl-4-nitrobenzene-l,2-diamine as a red solid.Step 2

[0265] To a stirred solution of Nl,N2-dineopentyl-4-nitrobenzene-l,2-diamine (59.0 g, 0.201 mol) in MeOH (590.0 mL, 10.0 vol) was added Raney Ni (17.0 g, 20% w / w) and pivalic anhydride (37.0 g, 0.201 mol) at room temperature in an autoclave. Then, hydrogen pressure was added (10 kg) into the reaction mass and stirred for 16 h. After completion of reaction (monitored by TLC), the mixture was filtered through celite bed and washed the bed with methanol (200 mL). The collected filtrate was evaporated under vacuum to afford 91 g of crude. The obtained crude was purified by silica gel column chromatography (100-200 mesh) eluting with 5-8% ethyl acetate in hexane to afford 37.0 g of compound 22 (>99 % pure by HPLC 260 nm, Mass (m / z): 348.29 [M+H]+) as light purple solid.

[0266] 1H NMR (400 MHz, DMSO ): 5 8.72 (s, 1H), 6.89 (d, J= 2.4 Hz, 1H), 6.85 (dd,J= 8.4, 2.4 Hz, 1H), 6.52 (d, J= 8.4 Hz, 1H), 4.23 (t, J= 6.4 Hz, 1H), 3.91 (t, J= 6.4 Hz, 1H), 2.79 (d, J= 6.0 Hz, 2H), 2.74 (d, J= 6.4 Hz, 2H), 1.18 (s, 9H), 0.99 (s, 9H), 0.96 (s, 9H).

[0267] 13C NMR (100 MHz, DMSO-t / e): 5 175.99, 138.96, 133.73, 131.89, 113.05,110.06, 105.02, 57.07, 56.19, 32.37, 32.24, 28.17, 28.15, 27.90.EXAMPLE 10Oxidative Induction Time (OIT) Performance of Compounds of the Disclosure

[0268] The oxidative induction time (OIT) of selected Compounds of the Disclosure was evaluated. OIT is measured according to a procedure carried out in a differential scanning calorimeter (DSC; TA Instruments, Q200). In this procedure, a sample is held in a cell and heated under a nitrogen atmosphere to a preselected temperature. Oxygen (O2) is then introduced to the cell and the length of time before the onset of degradation, as observed by the initiation of an endothermic process in the DSC trace, is measured.

[0269] 0.5 wt % of a Compound of the Disclosure, Afl-(4-methylpentan-2-yl)-Af4- phenylbenzene-l,4-diamine (6PPD), or no antidegradant (blank) was mixed with cispolyisoprene or isoprene homopolymer (LIR-30 grade) and heated isothermally at 150 °C or 160 °C in O2. The OIT in minutes is shown in Table 4. As indicated by the data in Table 4, Compounds of the Disclosure demonstrate antioxidant activity compared to the blank control.Table 4

[0270] 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 awide 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:R1is selected from the group consisting of optionally substituted C1-C12 alkyl, -CHRlcRld, -C(=O)R7, C3-C6 cycloalkyl, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;Rlais selected from the group consisting of hydrogen and C1-C4 alkyl;Rlcis selected from the group consisting of optionally substituted phenyl, 4- to 6- membered heterocyclyl, C3-C6 cycloalkyl, and optionally substituted 5- or 6-membered heteroaryl;Rldis selected from the group consisting of hydrogen and C1-C9 alkyl;R2, R3, and R4are independently selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, Ci-Cs alkoxy, Ci-Cs alkylthio, -C(=O)OR7, -OC(=O)R7, -C(=O)NR7R8, -NR7C(=O)R8, -NR7R8, -OH, -SH, -SC(=O)R7, -SC(=O)SR7, -SC(=O)NR7R8, -NR7C(=O)SR8, -NR7C(=S)SR8, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;X5is selected from the group consisting of -CR5aR5b-, -NR5a-, -O-, and -S-;R5ais absent or is selected from the group consisting of hydrogen and C1-C4 alkyl;R5bis selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, optionally substituted phenyl, -C(=O)OR7, -C(=O)NR7R8, -C(=O)SR7, -CH2OR7, -CH2OC(=O)R7, andR6ais absent or is selected from the group consisting of hydrogen and C1-C4 alkyl;R5is selected from the group consisting of hydrogen, optionally substituted C1-C12 alkyl, -CHR5cR5d, C3-C6 cycloalkyl, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl; orR5and R6taken together with the atoms to which they are attached form an optionally substituted 5- or 6-membered heterocyclyl or an optionally substituted 5- or 6- membered heteroaryl;R5Cis selected from the group consisting of optionally substituted phenyl, 4- to 6- membered heterocyclyl, C3-C6 cycloalkyl, and optionally substituted 5- or 6-membered heteroaryl;R5dis selected from the group consisting of hydrogen and C1-C9 alkyl;R6is selected from the group consisting of optionally substituted C1-C12 alkyl, -CHR6bR6c, C3-C6 cycloalkyl, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl; orR5and R6taken together with the atoms to which they are attached form an optionally substituted 5- or 6-membered heterocyclyl or an optionally substituted 5- or 6- membered heteroaryl;R6bis selected from the group consisting of optionally substituted phenyl, 4- to 6- membered heterocyclyl, C3-C6 cycloalkyl, and optionally substituted 5- or 6-membered heteroaryl;R6Cis selected from the group consisting of hydrogen and C1-C9 alkyl;R7and R8at each occurrence are independently selected from the group consisting of hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl;Z at each occurrence is independently selected from the group consisting of -O-, -S-, and -NR9-;R5e, R5f, R5g, and R5hat each occurrence are independently selected from the group consisting of hydrogen, C1-C12 alkyl, and optionally substituted phenyl; andR9at each occurrence is independently selected from the group consisting of hydrogen and Ci-Ce alkyl.

2. The compound of claim 1, or a salt, solvate, or stereoisomer thereof, wherein R5and R6taken together with the atoms to which they are attached form an optionally substituted 5- or 6-membered heterocyclyl or an optionally substituted 5- or 6-membered heteroaryl.The compound of claim 2, or a salt, solvate, or stereoisomer thereof, having Formula (II):(II), wherein: when X5is -CR5aR5b- or -NR5a-, then = is a single or a double bond, and when X5is -O- or -S-, then = is a single bond; with the proviso that when = is a double bond, then R5aand R12bare absent;R10is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, optionally substituted phenyl, -C(=O)OR7, -C(=O)NR7R8, -C(=O)SR7, -CH2OR7, -CH2OC(=O)R7, andR11is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl; orR10and R11taken together with the carbon atom to which they are attached form a C3-C12 cycloalkyl; andR12aand R12bare independently selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl.The compound of claim 3, or a salt, solvate, or stereoisomer thereof, having Formula (III):

5. The compound of claim 3, or a salt, solvate, or stereoisomer thereof, having Formula6. The compound of claim 4 or 5, or a salt, solvate, or stereoisomer thereof, wherein R5bis hydrogen, methyl, or optionally substituted phenyl.

7. The compound of claim 5 or 6, or a salt, solvate, or stereoisomer thereof, wherein R5ais hydrogen or methyl.

8. The compound of any one of claims 3-7, or a salt, solvate, or stereoisomer thereof, wherein R10and R11are hydrogen.

9. The compound of any one of claims 3-7, or a salt, solvate, or stereoisomer thereof, wherein R10and R11are methyl.

10. The compound of any one of claims 3-7, or a salt, solvate, or stereoisomer thereof, wherein R12ais hydrogen.

11. The compound of claim 3, or a salt, solvate, or stereoisomer thereof, having Formula (V):(V).

12. The compound of claim 3, or a salt, solvate, or stereoisomer thereof, having Formula (VI):(VI).

13. The compound of claim 3, or a salt, solvate, or stereoisomer thereof, having Formula (VII):

14. The compound of any one of claims 11-13, or a salt, solvate, or stereoisomer thereof, wherein R10, R11, R12a, and R12bare hydrogen.

15. The compound of claim 2, or a salt, solvate, or stereoisomer thereof, having Formula (VIII):(VIII), wherein:= is a single or a double bond, with the proviso that when = is a double bond, then R6aand R13are absent; andR13and R14are selected from the group consisting of hydrogen and C1-C4 alkyl.

16. The compound of claim 15, or a salt, solvate, or stereoisomer thereof, having Formula(IX):with the proviso that when = is a double bond, then R6aand R13are absent.

17. The compound of claim 16, or a salt, solvate, or stereoisomer thereof, wherein if = is a double bond, R14is methyl, and R2, R3, and R4are hydrogen, then R1is not:

18. The compound of claim 15, or a salt, solvate, or stereoisomer thereof, having Formula(X):with the proviso that when = is a double bond, then R6aand R13are absent.

19. The compound of claim 18, or a salt, solvate, or stereoisomer thereof, wherein if = is a double bond, R14is methyl, and R2, R3, and R4are hydrogen, then R1is not:

20. The compound of claim 15, or a salt, solvate, or stereoisomer thereof, having Formula (XI):(XI), with the proviso that when = is a double bond, then R6aand R13are absent.

21. The compound of any one of claims 15-20, or a salt, solvate, or stereoisomer thereof, wherein = is a double bond.

22. The compound of any one of claims 15-20, or a salt, solvate, or stereoisomer thereof, wherein = is a single bond.

23. The compound of claim 22, or a salt, solvate, or stereoisomer thereof, wherein R6ais hydrogen.

24. The compound of any one of claims 15-20, 22, or 23, or a salt, solvate, or stereoisomer thereof, wherein R13and R14are hydrogen or methyl.

25. The compound of claim 21, or a salt, solvate, or stereoisomer thereof, wherein R14is methyl.

26. The compound of claim 2, or a salt, solvate, or stereoisomer thereof, having Formula(XII):(XII), wherein:= is a single or a double bond, with the proviso that when = is a double bond, then R11and R12bare absent;R10is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, optionally substituted phenyl, -C(=O)OR7, -C(=O)NR7R8, -C(=O)SR7, -CH2OR7, -CH2OC(=O)R7, andR11is absent or is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl; orR10and R11taken together with the carbon atom to which they are attached form a C3-C12 cycloalkyl;R12ais selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl; andR12bis absent or is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl.

27. The compound of claim 26, or a salt, solvate, or stereoisomer thereof, wherein X5is - CR5aR5b-.

28. The compound of claim 27, or a salt, solvate, or stereoisomer thereof, wherein R5ais hydrogen or methyl.

29. The compound of claim 27 or 28, or a salt, solvate, or stereoisomer thereof, wherein R5bis hydrogen, C1-C9 alkyl, or optionally substituted phenyl.

30. The compound of any one of claims 26-29, or a salt, solvate, or stereoisomer thereof, wherein R10is hydrogen, C1-C9 alkyl, or optionally substituted phenyl.

31. The compound of any one of claims 26-30, or a salt, solvate, or stereoisomer thereof, wherein R6ais hydrogen or methyl.

32. The compound of any one of claims 26-31, or a salt, solvate, or stereoisomer thereof, wherein = is a single bond.

33. The compound of any one of claims 26-31, or a salt, solvate, or stereoisomer thereof, wherein = is a double bond.

34. The compound of claim 32, or a salt, solvate, or stereoisomer thereof, wherein R11is hydrogen or C1-C9 alkyl.

35. The compound of claim 32, or a salt, solvate, or stereoisomer thereof, wherein R12bis hydrogen or C1-C9 alkyl.

36. The compound of claim 2, or a salt, solvate, or stereoisomer thereof, having Formula (XIII):wherein: each = is independently a single or a double bond; when X5is -CR5aR5b- or -NR5a-, then the = attached to X5is a single or a double bond, and when X5is -O- or -S-, then the == attached to X5is a single bond, with the provisos that when the = attached to X5is a double bond, then R12bis absent, and when the = attached to N is a double bond, then R11is absent;R10is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, optionally substituted phenyl, -C(=O)OR7, -C(=O)NR7R8, -C(=O)SR7, -CH2OR7, - CH2OC(=O)R7, andR11is absent or is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl; orR10and R11taken together with the carbon atom to which they are attached form a C3-C12 cycloalkyl;R12ais absent or is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, optionally substituted phenyl, -C(=O)OR7, -C(=O)NR7R8, -C(=O)SR7, -CH2OR7, - CH2OC(=O)R7, andR12bis selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl; orR12aand R12btaken together with the carbon atom to which they are attached form a C3-C12 cycloalkyl;R13ais selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl; andR13bis selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl.

37. The compound of claim 36, or a salt, solvate, or stereoisomer thereof, having Formula (XIV):

38. The compound of claim 36, or a salt, solvate, or stereoisomer thereof, having Formula (XV):

39. The compound of any one of claims 36-38, or a salt of solvate thereof, wherein wherein R6ais hydrogen or methyl.

40. The compound of any one of claims 36-39, or a salt of solvate thereof, wherein R10is hydrogen or C1-C9 alkyl.

41. The compound of claim 36 or 38, or a salt of solvate thereof, wherein R11is hydrogen or C1-C9 alkyl.

42. The compound of any one of claims 36-41, or a salt of solvate thereof, wherein R12ais hydrogen or C1-C9 alkyl.

43. The compound of claim 36 or 37, or a salt of solvate thereof, wherein R12bis hydrogen or C1-C9 alkyl.

44. The compound of any one of claims 36-43, or a salt of solvate thereof, wherein R13ais hydrogen or C1-C9 alkyl.

45. The compound of any one of claims 36-44, or a salt of solvate thereof, wherein R13bis hydrogen or C1-C9 alkyl.

46. The compound of any one of claims 2-45, or a salt, solvate, or stereoisomer thereof, wherein R1is C1-C12 alkyl.

47. The compound of claim 1, or a salt, solvate, or stereoisomer thereof, wherein:R5is selected from the group consisting of hydrogen, optionally substituted C1-C12 alkyl, -CHR5cR5d, C3-C6 cycloalkyl, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl; andR6is selected from the group consisting of optionally substituted C1-C12 alkyl, -CHR6bR6c, C3-C6 cycloalkyl, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl.

48. The compound of claim 47, or a salt, solvate, or stereoisomer thereof, wherein Rlais hydrogen.

49. The compound of claim 47 or 48, or a salt, solvate, or stereoisomer thereof, wherein R1is C1-C12 alkyl.

50. The compound of any one of claims 47-49, or a salt, solvate, or stereoisomer thereof, wherein X5is -CR5aR5b-.

51. The compound of claim 50, or a salt, solvate, or stereoisomer thereof, wherein R5aand R5bare hydrogen.

52. The compound of claim 50, or a salt, solvate, or stereoisomer thereof, wherein R5aand R5bare C1-C4 alkyl.

53. The compound of any one of claims 47-49, or a salt, solvate, or stereoisomer thereof, wherein X5is -NR5a-.

54. The compound of claim 53, wherein R5ais hydrogen.

55. The compound of any one of claims 47-49, or a salt, solvate, or stereoisomer thereof, wherein X5is -O-.

56. The compound of any one of claims 47-55, or a salt, solvate, or stereoisomer thereof, wherein R5is C1-C12 alkyl.

57. The compound of any one of claims 50-52, or a salt, solvate, or stereoisomer thereof, wherein R5is hydrogen.

58. The compound of any one of claims 47-57, or a salt, solvate, or stereoisomer thereof, wherein R6is C1-C12 alkyl.

59. The compound of any one of claims 47-58, or a salt, solvate, or stereoisomer thereof, wherein R6ais hydrogen.

60. The compound of any one of claims 1-59, or a salt, solvate, or stereoisomer thereof, wherein R2, R3, and R4are independently hydrogen or methyl.

61. The compound of claim 60, or a salt, solvate, or stereoisomer thereof, wherein R4is methyl.

62. The compound of claim 60 or 61, or a salt, solvate, or stereoisomer thereof, wherein R2and R3are hydrogen.

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

64. A composition comprising:(i) the compound of any one of claims 1-63; 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 antidegradant.

65. The composition of claim 64, wherein the composition comprises one or more elastomers.

66. The composition of claim 65, wherein the composition comprises from about 0.1 wt / wt % to about 10 wt / wt % of the compound and from about 5 wt / wt % to about 95 wt / wt % of the one or more elastomers.

67. The composition of any one of claims 64-66, wherein the one or more elastomers comprise natural rubber (NR).

68. The composition of claim 67, wherein the one or more elastomers comprises from about 5 wt / wt % to about 100 wt / wt % natural rubber (NR).

69. The composition of claim 67 or 68, wherein the natural rubber comprises rubber derived from an alternative rubber plant.

70. The composition of claim 69, wherein the alternative rubber plant is Parthenium argentatum (guayule) or Taraxacum kok-saghyz (Russian dandelion).

71. The composition of any one of claims 65-70, wherein the one or more elastomers comprise synthetic rubber.

72. The composition of claim 71, 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.

73. The composition of claim 72, 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.

74. The composition of claim 73, wherein the unsaturated rubber comprises styrene butadiene rubber (SBR).

75. The composition of claim 74, wherein the one or more elastomers comprise from about 5 wt / wt % to about 100 wt / wt % styrene butadiene rubber (SBR).

76. The composition of any one of claims 73-75, wherein the unsaturated rubber comprises polybutadiene rubber (BR).

77. The composition of claim 76, wherein the one or more elastomers comprise from about 5 wt / wt % to about 80 wt / wt % polybutadiene rubber (BR).

78. The composition of any one of claims 73-77, wherein the unsaturated rubber comprises butyl rubber (HR).

79. The composition of claim 78, wherein the one or more elastomers comprise from about 1 wt / wt % to about 30 wt / wt % butyl rubber (IIR).

80. The composition of any one of claims 72-79, 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.

81. The composition of claims any one of claims 65-80, wherein the one or more elastomers further comprises recycled rubber.

82. The composition of any one of claims 65-81, wherein the composition comprises from about 0.1 phr to about 10 phr of the compound.

83. The composition of claim 82, wherein the composition comprises from about 0.5 phr to about 5 phr of the compound.

84. The compound of claim 83, wherein the composition comprises from about 1 phr to about 5 phr of the compound.

85. The composition of any one of claims 64-84, wherein the composition comprises one or more fillers.

86. The composition of claim 85, wherein the composition comprises from about 0.1 wt / wt % to about 10 wt / wt % of the compound and from about 5 wt / wt % to about 95 wt / wt % of the one or more fillers.

87. The composition of claims 85 or 86, wherein the composition comprises from about 30 phr to about 500 phr of one or more fillers.

88. The composition of any one of claims 85-87, 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.

89. The composition of claim 88, wherein the one or more fillers comprise silica.

90. The composition of claim 89, wherein the silica is derived from rice husks.

91. The composition of any one of claims 85-88, wherein the one or more fillers comprise carbon black.

92. The composition of any one of claims claim 64-91, wherein the composition comprises one or more rubber chemicals.

93. The composition of claim 92, wherein the composition comprises from about 0.1 wt / wt % to about 10 wt / wt % of the compound and from about 5 wt / wt % to about 95 wt / wt % of one or more rubber chemicals.

94. The composition of claims 92 or 93, wherein the composition comprises from about 0.1 phr to about 30 phr of one or more rubber chemicals.

95. The composition of claim 94, wherein the composition comprises from about 1 phr to about 20 phr of one or more rubber chemicals.

96. The composition of any one of claims 92-95, 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.

97. The composition of claim 96, wherein the one or more rubber chemicals comprise one or more vulcanizing agents.

98. The composition of claim 97, wherein the one or more vulcanizing agents comprise sulfur, peroxide, resin, or a combination thereof.

99. The composition of claim 98, wherein the sulfur is octasulfur (Ss), cyclododecasulfur (S12), polymeric sulfur, or a combination thereof.

100. The composition of claim 98, 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), 1, l-di(tert-butylperoxy)-3,3,5-trimethylcyclohexane (TMC), or a combination thereof.

101. The composition of claim 98, wherein the resin is a bonding resin.

102. The composition of claims 96-101, wherein the one or more rubber chemicals comprise one or more accelerators.

103. The composition of claim 102, 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.

104. The composition of claim 103, wherein the guanidine is diphenylguanidine (DPG).

105. The composition of claim 103, 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.

106. The composition of claim 103, wherein the sulfenamide comprises V- / c / 7-butyl-2- benzothiazylsulfenamide (TBBS), 7V-cyclohexylbenzothiazol-2-sulfenamide (CBS), dicyclohexyl-2-benzothiazolesulfenamide (DCBS), V-oxy di ethylene benzothiazole sulfenamide (OBTS), V-oxydiethylenethiocarbamyl-V'-oxy diethylene sulfenamide (OTOS), thiocarbamyl sulfenamide, or a combination thereof.

107. The composition of claim 103, 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.

108. The composition of claim 103, 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.

109. The composition of any one of claims 96-108, wherein the one or more rubber chemicals comprise one or more activators.

110. The composition of claim 109, wherein the one or more activators comprise a metal oxide, an acid, a metal complex, or a combination thereof.

111. The composition of claim 110, wherein the metal oxide comprises zinc oxide, magnesium oxide, lead oxide, or a combination thereof.

112. The composition of claim 110, wherein the acid comprises stearic acid, lauric acid, or a combination thereof.

113. The composition of claim 110, wherein the metal complex comprises zinc ethylhexanoate.

114. The composition of any one of claims 96-113, wherein the one or more rubber chemicals comprise one or more pre-vulcanization inhibitors.

115. The composition of claim 114, wherein the one or more pre-vulcanization inhibitors comprise 7V-(cyclohexylthio)phthalimide (CTP), benzoic anhydride, salicylic anhydride, phthalic anhydride, or a combination thereof.

116. The composition of any one of claims 64-115, wherein the composition comprises one or more plasticizers.

117. The composition of claim 116, wherein the composition comprises from about 0.1 wt / wt % to about 10 wt / wt % of the compound and from about 5 wt / wt % to about 95 wt / wt % of one or more plasticizers.

118. The composition of claims 116 or 117, wherein the composition comprises from about 0.1 phr to about 30 phr of one or more plasticizers.

119. The composition of claim 118, wherein the composition comprises from about 1 phr to about 20 phr of one or more plasticizers.

120. The composition of any one of claims 116-119, 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.

121. The composition of claim 120, wherein the mineral oil is naphthenic oil, paraffinic oil, or aromatic oil.

122. The composition of claim 120, wherein the naturally derived oil is soybean oil, vegetable oil, or orange oil.

123. The composition of any one of claims 64-122, wherein the composition further comprises one or more additional anti degradants.

124. The composition of claim 123, wherein the composition comprises from about 0.1 wt / wt % to about 10 wt / wt % of the compound and from about 5 wt / wt % to about 95 wt / wt % of the one or more additional anti degradants.

125. The composition of claim 123 or 124, wherein the one or more additional anti degradants are present in an amount of from about 0.001 phr to about 10 phr.

126. The composition of claim 125, wherein the one or more additional anti degradants are present in an amount of from about 0.1 phr to about 5 phr.

127. The composition of claim 126, wherein the one or more additional anti degradants are present in an amount of from about 0.5 phr to about 5 phr.

128. The composition of claim 127, wherein the one or more additional anti degradants are present in an amount of from about 1 phr to about 5 phr.

129. The composition of any one of claims 123-128, wherein one additional antidegradant is an antioxidant.

130. The composition of any one of claims 123-128, wherein one additional antidegradant is an antiozonant.

131. The composition of any one of claims 123-130, wherein the one additional antidegradant is a paraphenylenediamine (PPD), a trimethyldihydroquinoline (TMQ), a phenolic, an alkylated diphenylamine (DPA), or a diphenylamine-ketone condensate.

132. The composition of claim 131, wherein the PPD is 7V1-(4-methylpentan-2-yl)-A4- phenylbenzene- 1 ,4-diamine (6PPD), N-( 1 ,4-di methyl pentyl )-A'-phenyl -p- phenylenediamine (7PPD), 7V1-phenyl-A4-(propan-2-yl)benzene-l,4-diamine (IPPD), A,A'-di- ec-butyl- / ?-phenylenediamine (44PD), A,A'-bis(l,3-dimethylbutyl)-p- phenylenediamine (66PD), 7V,A'-bis(l ,4-di methyl pentyl )-p-phenylenedi amine (77PD), or N-N -di octyl - -ph eny 1 enedi amine (88PD) .

133. The composition of claim 132, wherein the PPD is 6PPD.

134. The composition of claim 131, wherein the TMQ is 2,2,4-trimethyl-l,2-dihydroquinoline or an oligomer or polymer thereof.

135. A composition comprising the compound of any one of claims 1-63 and one or more carriers.

136. A process for preparing the composition of claim 135, the process comprising admixing the compound and the one or more carriers.

137. A vulcanized elastomeric article comprising the compound of any one of claims 1-63.

138. A vulcanized elastomeric article prepared using the composition of any one of claims 65- 134.

139. The vulcanized elastomeric article of claims 137 or 138, wherein the vulcanized elastomeric article is a tire.

140. The vulcanized elastomeric article of claim 139, 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.

141. The vulcanized elastomeric article of claims 137 or 138, wherein the vulcanized elastomeric article is a component of a tire.

142. The vulcanized elastomeric article of claim 141, wherein the component is a bead, a belt, a body ply, an inner liner, a sidewall, an undertread, or a tread.

143. The vulcanized elastomeric article of claims 137 or 138, 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.

144. A process for preparing a vulcanized elastomeric article, the process comprising:(a) forming the composition of any one of claims 65-134 into a formed shape; and(b) vulcanizing the formed shape to provide a vulcanized elastomeric article.

145. The process of claim 144, wherein the vulcanizing is performed at an average temperature of from about 120 °C to about 180 °C.

146. The process of claim 145, wherein the vulcanizing is performed at an average temperature of from about 140 °C to about 160 °C.

147. The process of any one of claims 144-146, wherein the vulcanized elastomeric article is a tire.

148. The process of claim 147, 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.

149. The process of any one of claims 144-146, wherein the vulcanized elastomeric article is a component of a tire.

150. The process of claim 149, wherein the component is a bead, a belt, a body ply, an inner liner, a sidewall, an undertread, or a tread.

151. The process of any one of claims 144-146, 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.

152. A lubricant composition comprising a lubricant and the compound of any one of claims 1- 63.

153. A combustible fuel composition comprising a combustible fuel and the compound of any one of claims 1-63.

154. A fuel additive composition comprising a fuel additive and the compound of any one of claims 1-63.

155. A process for retreading tires, the process comprising:(a) applying the composition of any one of claims 87-135 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.

156. A kit comprising the composition of any one of claims 64-135 and instructions for using the composition in a vulcanizable elastomeric composition.

157. A kit comprising the composition of any one of claims 64-135 and instructions for using the composition to prepare a vulcanized elastomeric article.

158. The composition of claim 64, wherein the composition comprises from about 0.1 wt / wt% to about 10 wt / wt% of the compound.

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