Quinolineamine and pyridoquinoline antidegradant compounds and uses thereof

Abstract

The present disclosure provides compounds represented by Formula (I): (I), or salts or solvates thereof, wherein R1, R1c, R2a, R2b, R2c, R3a, R3b, R3c, R3d, R3e, and are as defined in the specification. The present disclosure provides compounds represented by Formula (IV): (IV), or salts or solvates thereof, wherein R8a, R8b, R9a, R9b, R9c, R9d, R9e, R10a, R10b, R10c, R10d, R10e, 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

QUINOLINEAMINE AND PYRIDOQUINOLINE 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), (II), (Ila), (III), (Illa), (IV), (V), and (VI), below, collectively referred to herein as "Compounds of the Disclosure" or individually as a "Compound of the Disclosure."

[0007] The present disclosure also provides compositions comprising:(i) a Compound of the Disclosure; and(ii) one or more elastomers; or(iii) one or more fillers; or(iv) one or more rubber chemicals; or(v) one or more plasticizers; or(vi) one or more additional antidegradants; or(vii) a combination of one or more elastomers, one or more fillers, one or more rubber chemicals, one or more plasticizers, and / or one or more additional anti degradants, collectively referred to herein as "Compositions of the Disclosure" or individually as a "Composition of the Disclosure."

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

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

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

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

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

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

[0014] The present disclosure also provides processes for preparing a composition comprising a Compound of the Disclosure and one or more carriers, the process comprising admixing the compound and the one or more carriers.

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

[0016] The present disclosure also provides vulcanized elastomeric articles prepared using a composition described herein, e.g., Compositions of the Disclosure or compositions comprising a Compound of the Disclosure and one or more carriers.

[0017] The present disclosure also provides a process for preparing the vulcanized elastomeric articles described herein, the process comprising:(a) forming a composition described herein into a formed shape; and(b) vulcanizing the formed shape to provide a vulcanized elastomeric article.

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

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

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

[0021] The present disclosure also provides a process for retreading tires, the process comprising:(a) applying a composition described herein to a tire;(b) disposing a pre-vulcanized tread around the tire;(c) disposing a curing envelope around the tire; and(d) vulcanizing the tire.

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

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

[0024] Additional embodiments and advantages of the disclosure will be set forth, in part, in the description that follows, and will flow from the description, or can be learned by practice of the disclosure. The embodiments and advantages of the disclosure will be realized and attained by means of the elements and combinations particularly pointed out in the appended claims.

[0025] It is to be understood that both the foregoing summary and the following detailed description are exemplary and explanatory only, and are not restrictive of the invention as claimed.BRIEF DESCRIPTION OF THE DRAWINGS

[0026] Fig. l is a line graph depicting a13C nuclear magnetic resonance (NMR) spectrum of Intermediate Compound 1-1 in tA-dimethyl sulfoxide ( e-DMSO).

[0027] Fig. 2 is a line graph depicting aJH NMR spectrum of Compound 1 in tfc-DMSO.

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

[0029] Fig. 4 is a line graph depicting aJH NMR spectrum of Compound 3 in tfc-DMSO.

[0030] Fig. 5 is a line graph depicting a13C NMR spectrum of Compound 3 in e-DMSO.

[0031] Fig. 6 is a line graph depicting a13C NMR spectrum of Compound 6 in t / s-THF.

[0032] Fig. 7 is a line graph depicting aJH NMR spectrum of Compound Bl in d- trifluoroacetic acid (t / -TFA).

[0033] Fig. 8 is a line graph depicting a13C NMR spectrum of Compound Bl in t / -TFA.

[0034] Fig. 9 is a line graph depicting aJH NMR spectrum of Compound B2 in d- trifluoroacetic acid (t / -TFA).

[0035] Fig. 10 is a line graph depicting a13C NMR spectrum of Compound B2 in t / -TFA.

[0036] Fig. 11 is a line graph depicting a13C NMR spectrum of Compound 33.

[0037] Fig. 12 is a line graph depicting a13C NMR spectrum of Compound 32.

[0038] Fig. 13 is a line graph showing force retention as a function of time for sidewall compounds comprising Compound 1 or no antidegradant under dynamic conditions.

[0039] Fig. 14 is a line graph showing force retention as a function of time for sidewall compounds comprising Compound Bl or no antidegradant under dynamic conditions.

[0040] Fig. 15 is a line graph showing force retention as a function of time for tread compounds comprising Compound 1 or no antidegradant under dynamic conditions.

[0041] Fig. 16 is a line graph showing force retention as a function of time for sidewall compounds comprising Compound 6 or no antidegradant under dynamic conditions.

[0042] Fig. 17 is a line graph showing force retention as a function of time for tread compounds comprising Compound 6 or no antidegradant under dynamic conditions.DETAILED DESCRIPTION

[0043] In one embodiment, Compounds of the Disclosure are compounds having Formula (I):(I), or a salt, solvate, or stereoisomer thereof, wherein:= is a single or a double bond;R1is selected from the group consisting of optionally substituted C1-C12 alkyl, optionally substituted C2-C6 alkenyl, -CHRlaRlb, C3-C7 cycloalkyl, 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, -C(=O)R4, -C(=O)OR4, and -SO2R4;Rlais 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;Rlbis selected from the group consisting of hydrogen and C1-C9 alkyl;Rlcis selected from the group consisting of hydrogen and Ci-Ce alkyl;R2a, R2b, and R2care 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)OR4, -OC(=O)R4, -C(=O)NR4R5, -NR4C(=O)R5, -NR4R5, -OH, -SH, -S C(=O)R4, -SC(=O)SR4, -SC(=O)NR4R5, -NR4C(=O)SR5, -NR4C(=S)SR5, 4- to 6- membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6- membered heteroaryl;R3ais selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, optionally substituted phenyl, -C(=O)OR4, -C(=O)NR4R5, -C(=O)SR4, -CH2OR4, -CH2OC(=O)R4, andR3bis selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl; orR3aand R3btaken together with the carbon atom to which they are attached form a C3-C12 cycloalkyl;R3Cis selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, optionally substituted phenyl, -C(=O)OR4, -C(=O)NR4R5, -C(=O)SR4, -CH2OR4, -CH2OC(=O)R4, andR3dis selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl; orR3Cand R3dtaken together with the two carbon atoms to which they are attached form a C3-C12 cycloalkyl;R3eis selected from the group consisting of hydrogen, Ci-Ce alkyl, optionally substituted C2-C6 alkenyl, C3-C7 cycloalkyl, -C(=O)R4, -C(=O)OR4, and -SO2R4;Z at each occurrence is independently selected from the group consisting of -O-, -S-, and -NR7-;R4at each occurrence is independently selected from the group consisting of hydrogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C7 cycloalkyl, and optionally substituted phenyl;R5at each occurrence is independently selected from the group consisting of hydrogen, C1-C9 alkyl, C3-C7 cycloalkyl, and optionally substituted phenyl;R6a, R6b, R6C, and R6dat each occurrence are independently selected from the group consisting of hydrogen, C1-C12 alkyl, and optionally substituted phenyl; and R7at each occurrence is independently selected from the group consisting or hydrogen and Ci-Ce alkyl, with the proviso that the compound of Formula (I) is not 2,2,4-trimethyl-N- phenyl- 1 ,2-dihydroquinolin-6-amine, 2,2,4-trimethyl-N-phenyl- 1 ,2,3 ,4-tetrahydroquinolin-6- amine, or 2,2,4-trimethyl-N-(p-tolyl)-l,2-dihydroquinolin-6-amine:

[0044] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein R2a, R2b, and R2care hydrogen.

[0045] In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein if R2a, R2b, and R2care hydrogen, R3a, R3b, and R3care methyl, and R3dis hydrogen, then R1is selected from the group consisting of optionally substituted C1-C12 alkyl, -CHRlaRlb, C3-C7 cycloalkyl, 4- to 6-membered heterocyclyl, and optionally substituted 5- or 6-membered heteroaryl.In some embodiments, Compounds of the Disclosure are compounds having Formula (I), wherein if R1is phenyl, R2a, R2b, and R2care hydrogen, R3bis methyl, and R3dis hydrogen, then R3ais selected from the group consisting of hydrogen, halogen, C2- C9 alkyl, optionally substituted phenyl, C(=O)OR4, C(=O)NR4R5, C(=O)SR4, CH2OR4, CH2OC(=O)R4, and

[0046] R3Cis selected from the group consisting of hydrogen, halogen, C2-C9 alkyl, optionally substituted phenyl, -C(=O)OR4, -C(=O)NR4R5, -C(=O)SR4, -CH2OR4, -CH2OC(=O)R4, and

[0047] In another embodiment, Compounds of the Disclosure are compounds having Formula (II):(II), or a salt, solvate, or stereoisomer thereof, wherein R1, Rlc, R2a, R2b, R2c, R3a, R3b, R3c, R3d, and R3eare as defined in connection with Formula (I).

[0048] In another embodiment, Compounds of the Disclosure are compounds havingFormula (Ila):or a salt, solvate, or stereoisomer thereof, wherein R1, Rlc, R3a, R3b, R3c, R3d, and R3eare as defined in connection with Formula (I).

[0049] In another embodiment, Compounds of the Disclosure are compounds havingFormula (III):or a salt, solvate, or stereoisomer thereof, wherein R1, Rlc, R2a, R2b, R2c, R3a, R3b, R3c, R3d, and R3eare as defined in connection with Formula (I).

[0050] In another embodiment, Compounds of the Disclosure are compounds havingFormula (Illa):

[0051] or a salt, solvate, or stereoisomer thereof, wherein R1, Rlc, R3a, R3b, R3c, R3d, and R3eare as defined in connection with Formula (I).

[0052] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (II), (Ila), (III), or (Illa), with the proviso that the compound ofFormulae (II), (Ila), (III), or (Illa) is not 2,2,4-trimethyl-N-phenyl-l,2-dihydroquinolin-6- amine or 2,2,4-trimethyl-N-phenyl-l,2,3,4-tetrahydroquinolin-6-amine.

[0053] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3a, R3b, and R3care independently selected from the group consisting of methyl, ethyl, propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, and nonyl.

[0054] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3a, R3b, and R3care methyl, ethyl, or iso-butyl.

[0055] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3aand R3care methyl.

[0056] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3aand R3care ethyl.

[0057] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3aand R3care iso-butyl.

[0058] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3bis methyl.

[0059] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3aand R3bare methyl; and R3cand R3dare hydrogen.

[0060] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3aand R3bare ethyl; and R3cand R3dare hydrogen.

[0061] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3ais ethyl; R3bis methyl; and R3cand R3dare hydrogen.

[0062] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3ais -C(=O)OR4, -C(=O)NR4R5, -C(=O)SR4, -CH2OR4, -CH2OC(=O)R4, or

[0063] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3ais -C(=O)OR4. In some embodiments, R3ais -C(=O)OEt.

[0064] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3ais -C(=O)NR4R5.

[0065] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3ais -C(=O)SR4.

[0066] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3ais -CH2OR4.

[0067] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3ais -CH2OC(=O)R4.

[0068] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3ais

[0069] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3cis -C(=O)OR4. In some embodiments, R3cis -C(=O)OEt.

[0070] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3cis -C(=O)NR4R5.

[0071] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3cis -C(=O)SR4.

[0072] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3cis -CH2OR4.

[0073] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3cis -CH2OC(=O)R4.

[0074] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3cis

[0075] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein Z is -O-. In some embodiments, Z is -S-. In some embodiments, Z is -NR7-. In some embodiments, R7is hydrogen. In some embodiments, R6a, R6b, R6c, and R6dare hydrogen.

[0076] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3aand R3btaken together with the carbon atom to which they are attached form a C3-C12 cycloalkyl.

[0077] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3aand R3btaken together with the carbon atom to which they are attached form a cyclobutyl, cyclopentyl, or cyclohexyl.

[0078] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3cand R3dtaken together with the two carbon atoms to which they are attached form a C3-C12 cycloalkyl.

[0079] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3cand R3dtaken together with the two carbon atoms to which they are attached form a cyclopentyl, a cyclopentenyl, a cyclohexyl, or a cyclohexenyl.

[0080] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein each R4is hydrogen or C1-C9 alkyl.

[0081] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein each R4is ethyl.

[0082] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein each R4is hydrogen.

[0083] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R1is optionally substituted phenyl.

[0084] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R1is C1-C12 alkyl.

[0085] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R1is methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, or nonyl.

[0086] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R1is:

[0087] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R1is -CHRlaRlb.

[0088] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein Rlais optionally substituted phenyl.

[0089] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein Rlais C3-C6 cycloalkyl.

[0090] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein Rlais optionally substituted 5- or 6- membered heteroaryl.

[0091] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein Rlais phenyl, 2-furyl, or 2- tetrahydrofuryl.

[0092] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein Rlais phenyl.

[0093] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein Rlais 2-furyl.

[0094] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein Rlais 2-tetrahydrofuryl.

[0095] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein Rlbis hydrogen or methyl.

[0096] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein Rlbis hydrogen.

[0097] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein Rlbis methyl.

[0098] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein Rlcis Ci-Ce alkyl.

[0099] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein Rlcis methyl.

[0100] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein Rlcis hydrogen.

[0101] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3eis Ci-Ce alkyl.

[0102] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3eis methyl.

[0103] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3eis ethyl.

[0104] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3eis hydrogen.

[0105] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3eis C3-C7 cycloalkyl.

[0106] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3eis cyclohexen-l-yl.

[0107] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3eis -C(=O)R4.

[0108] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3eis -C(=O)CH3.

[0109] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3eis -C(=O)OR4.

[0110] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3eis -C(=O)OC(CH3)3.

[0111] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3eis -SO2R4.

[0112] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3eis -SO2CH3.

[0113] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3eis -SC^CeHsCFF).

[0114] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3eis optionally substituted C2-C6 alkenyl.

[0115] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (I), (II), (Ila), (III), or (Illa), wherein R3eis:

[0116] 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

[0117] In another embodiment, Compounds of the Disclosure are compounds havingFormula (IV):or a salt, solvate, or stereoisomer thereof, wherein: each = is independently a single or a double bond;R8aand R8bare 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)OR4, -OC(=O)R4, -C(=O)NR4R5, -NR4C(=O)R5, -NR4R5, -OH, -SH, -SC(=O)R4, - SC(=O)SR4, -SC(=O)NR4R5, -NR4C(=O)SR5, -NR4C(=S)SR5, 4- to 6-memberedheterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio, and arylamino;R9ais selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, optionally substituted phenyl, -C(=O)OR4, -C(=O)NR4R5, -C(=O)SR4, -CH2OR4, -CH2OC(=O)R4, andR9bis selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl; orR9aand R9btaken together with the carbon atom to which they are attached form a C3-C12 cycloalkyl;R9Cis selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, optionally substituted phenyl, -C(=O)OR4, -C(=O)NR4R5, -C(=O)SR4, -CH2OR4, -CH2OC(=O)R4, andR9dis selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl; orR9Cand R9dtaken together with the two carbon atoms to which they are attached form aC3-C12 cycloalkyl;R9eis selected from the group consisting of hydrogen, Ci-Ce alkyl, optionally substitutedC2-C6 alkenyl, -C(=O)R4, -C(=O)OR4, and -SO2R4;R10ais selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, optionally substituted phenyl, -C(=O)OR4, -C(=O)NR4R5, -C(=O)SR4, -CH2OR4, -CH2OC(=O)R4, andR10bis selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl; orR10aand R10btaken together with the carbon atom to which they are attached form a C3- C12 cycloalkyl;R10cis selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, optionally substituted phenyl, -C(=O)OR4, -C(=O)NR4R5, -C(=O)SR4, -CH2OR4, -CH2OC(=O)R4, andR10dis selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl; orR10cand R10dtaken together with the two carbon atoms to which they are attached form a C3-C12 cycloalkyl;R10eis selected from the group consisting of hydrogen, Ci-Ce alkyl, optionally substituted C2-C6 alkenyl, -C(=O)R4, -C(=O)OR4, and -SO2R4;Z at each occurrence is independently selected from the group consisting of -O-, -S-, and -NR7-;R4at each occurrence is independently selected from the group consisting of hydrogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C7 cycloalkyl, and optionally substituted phenyl; andR5at each occurrence is independently selected from the group consisting of hydrogen, C1-C9 alkyl, C3-C7 cycloalkyl, and optionally substituted phenyl;R6a, R6b, R6C, and R6dat each occurrence are independently selected from the group consisting of hydrogen, C1-C12 alkyl, and optionally substituted phenyl; andR7at each occurrence is independently selected from the group consisting or hydrogen and Ci-Ce alkyl.

[0118] In another embodiment, Compounds of the Disclosure are compounds havingFormula (V):(V),

[0119] or a salt, solvate, or stereoisomer thereof, wherein R8a, R8b, R9a, R9b, R9c, R9d, R9e, Ri°a, R10b, R10c, R10d, and R10eare as defined in connection with Formula (IV).

[0120] In another embodiment, Compounds of the Disclosure are compounds having Formula (VI):

[0121] or a salt, solvate, or stereoisomer thereof, wherein R8a, R8b, R9a, R9b, R9c, R9d, R9e, Ri°a, R10b, R10c, R10d, and R10eare as defined in connection with Formula (IV).

[0122] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R8aand R8bare hydrogen.

[0123] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R8aand R8bare methyl.

[0124] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9a, R9b, and R9care independently selected from the group consisting of methyl, ethyl, propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tertbutyl, pentyl, hexyl, heptyl, octyl, and nonyl.

[0125] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9a, R9b, and R9care methyl, ethyl, or iso-butyl.

[0126] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9aand R9care methyl.

[0127] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9aand R9care ethyl.

[0128] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9aand R9care iso-butyl.

[0129] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9bis methyl.

[0130] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9aand R9bare methyl; and R9cand R9dare hydrogen.

[0131] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9aand R9bare ethyl; and R9cand R9dare hydrogen.

[0132] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9ais ethyl; R9bis methyl; and R9cand R9dare hydrogen.

[0133] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9ais -C(=O)OR4, -C(=O)NR4R5, -C(=O)SR4, -CH2OR4, -CH2OC(=O)R4, or

[0134] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9ais -C(=O)OR4. In some embodiments, R9ais -C(=O)OEt.

[0135] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9ais -C(=O)NR4R5.

[0136] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9ais -C(=O)SR4.

[0137] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9ais -CH2OR4.

[0138] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9ais -CH2OC(=O)R4.

[0139] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9ais

[0140] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9cis -C(=O)OR4. In some embodiments, R9cis -C(=O)OEt.

[0141] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9cis -C(=O)NR4R5.

[0142] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9cis -C(=O)SR4.

[0143] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9cis -CH2OR4.

[0144] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9cis -CH2OC(=O)R4.

[0145] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9cis

[0146] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10a, R10b, and R10care independently selected from the group consisting of methyl, ethyl, propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, and nonyl.

[0147] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10a, R10b, and R10care methyl, ethyl, or iso-butyl.

[0148] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10aand R10care methyl.

[0149] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10aand R10care ethyl.

[0150] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10aand R10care iso-butyl.

[0151] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10bis methyl.

[0152] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10aand R10bare methyl; and R10cand R10dare hydrogen.

[0153] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10aand R10bare ethyl; and R10cand R10dare hydrogen.

[0154] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10ais ethyl; R10bis methyl; and R10cand R10dare hydrogen.

[0155] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10ais -C(=O)OR4, -C(=O)NR4R5, -C(=O)SR4, -CH2OR4, -CH2OC(=O)R4, or

[0156] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10ais -C(=O)OR4. In some embodiments, R10ais -C(=O)OEt.

[0157] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10ais -C(=O)NR4R5.

[0158] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10ais -C(=O)SR4.

[0159] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10ais -CH2OR4.

[0160] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10ais -CH2OC(=O)R4.

[0161] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10ais

[0162] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10cis -C(=O)OR4. In some embodiments, R10cis -C(=O)OEt.

[0163] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10cis -C(=O)NR4R5.

[0164] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10cis -C(=O)SR4.

[0165] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10cis -CH2OR4.

[0166] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10cis -CH2OC(=O)R4.

[0167] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10cis

[0168] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein Z is -O-. In some embodiments, Z is -S-. In some embodiments, Z is -NR7-. In some embodiments, R7is hydrogen. In some embodiments, R6a, R6IR6C, and R6dare hydrogen.

[0169] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9aand R9btaken together with the carbon atom to which they are attached form a C3-C12 cycloalkyl.

[0170] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9aand R9btaken together with the carbon atom to which they are attached form a cyclobutyl, cyclopentyl, or cyclohexyl.

[0171] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10aand R10btaken together with the carbon atom to which they are attached form a C3-C12 cycloalkyl.

[0172] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10aand R10btaken together with the carbon atom to which they are attached form a cyclobutyl, cyclopentyl, or cyclohexyl.

[0173] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9cand R9dtaken together with the two carbon atoms to which they are attached form a C3-C12 cycloalkyl.

[0174] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9cand R9dtaken together with the two carbon atoms to which they are attached form a cyclopentyl, a cyclopentenyl, a cyclohexyl, or a cyclohexenyl.

[0175] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10cand R10dtaken together with the two carbon atoms to which they are attached form a C3-C12 cycloalkyl.

[0176] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10cand R10dtaken together with the two carbon atoms to which they are attached form a cyclopentyl, a cyclopentenyl, a cyclohexyl, or a cyclohexenyl.

[0177] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein each R4is hydrogen or C1-C9 alkyl.

[0178] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein each R4is ethyl.

[0179] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein each R4is hydrogen.

[0180] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9aand R10aare the same, e.g., R9aand R10aare both methyl, both ethyl, or both iso-butyl.

[0181] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9band R10bare the same, e.g., R9aand R10aare both methyl, both ethyl, or both iso-butyl.

[0182] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9cand R10care the same, e.g., R9aand R10aare both methyl, both ethyl, or both iso-butyl.

[0183] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9dand R10dare the same, e.g., R9aand R10aare both hydrogen.

[0184] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9eis Ci-Ce alkyl.

[0185] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9eis methyl.

[0186] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9eis ethyl.

[0187] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9eis hydrogen.

[0188] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9eis C3-C7 cycloalkyl.

[0189] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9eis cyclohexen-l-yl.

[0190] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9eis -C(=O)R4.

[0191] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9eis -C(=O)CH3.

[0192] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9eis -C(=O)OR4.

[0193] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9eis -C(=O)OC(CH3)3.

[0194] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9eis -SO2R4.

[0195] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R9eis -SO2CH3.

[0196] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein

[0197] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10eis Ci-Ce alkyl.

[0198] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10eis methyl.

[0199] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10eis ethyl.

[0200] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10eis hydrogen.

[0201] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10eis C3-C7 cycloalkyl.

[0202] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10eis cyclohexen-l-yl.

[0203] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10eis -C(=O)R4.

[0204] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10eis -C(=O)CH3.

[0205] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10eis -C(=O)OR4.

[0206] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10eis -C(=O)OC(CH3)3.

[0207] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10eis -SO2R4.

[0208] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10eis -SO2CH3.

[0209] In some embodiments, Compounds of the Disclosure are compounds having any one of Formulae (IV)-(VI), wherein R10eis -SCh CeHsCFF).

[0210] In some embodiments, Compounds of the Disclosure are any one or more of the compounds of Table 2, or a salt or solvate thereof.Table 2

[0211] 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.

[0212] Compounds of the Disclosure can be prepared by a three-step process comprising i) reacting a secondary arylamine with sodium nitrite in acid, ii) reducing the resulting nitroso intermediate to an amine, and iii) reacting the resulting amine with a ketone, e.g., acetone, or aldehyde, as shown in Scheme 1. Reduction of the nitroso intermediate to an amine can be carried out using any methods known in the art, such as treatment with sodium borohydride (NaBHf) in ethanol.Scheme 1

[0213] Compounds of the Disclosure can also be prepared by reacting a 1,4- diaminobenzene with a ketone, e.g., acetone, or aldehyde, as shown in Scheme 2.

[0214] Compounds of the Disclosure can also be prepared by further reduction of compounds synthesized using Scheme 1 or 2, as shown in Schemes 3 and 4, respectively. 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 3Definitions

[0215] The term "alkyl" as used herein by itself or as part of another group refers to a straight- or branched-chain aliphatic hydrocarbon containing one to twelve carbon atoms, i.e., a C1-C12 alkyl, or the number of carbon atoms designated, e.g., C1-C3 alkyl such as methyl, ethyl, propyl, or isopropyl; a C1-C4 alkyl such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or t-butyl; and so on. In one embodiment the alkyl is a straight-chain alkyl. In another embodiment, the alkyl is a branched-chain alkyl. In one embodiment, the alkyl is a Ci-Cs alkyl. In another embodiment, the alkyl is a Ci-Ce alkyl. In another embodiment, the alkyl is a C1-C4 alkyl. In another embodiment, the alkyl is a C1-C3 alkyl. 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.

[0216] 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.

[0217] The term "alkenyl" as used herein by itself or as part of another group refers to an alkyl group containing one, two, or three carbon-to-carbon double bonds. In one embodiment, the alkenyl group is a C2-C6 alkenyl group. In another embodiment, the alkenyl group is a C2-C4 alkenyl group. In another embodiment, the alkenyl group has one carbon-to-carbon double bond. Non-limiting exemplary alkenyl groups include ethenyl, propenyl, isopropenyl, butenyl, ec-butenyl, pentenyl, and hexenyl.

[0218] The term "optionally substituted alkenyl" as used herein by itself or as part of another refers to an alkenyl group that is either unsubstituted or substituted with one, two or three substituents, wherein each substituent is independently halo, nitro, cyano, hydroxy, amino (e.g., alkylamino, dialkylamino), haloalkyl, hydroxyalkyl, alkoxy,haloalkoxy, aryloxy, aralkyloxy, alkylthio, carboxamido, sulfonamido, alkylcarbonyl, arylcarbonyl, alkylsulfonyl, arylsulfonyl, ureido, guanidino, carboxy, carboxyalkyl, optionally substituted cycloalkyl, alkenyl, alkynyl, optionally substituted aryl, optionally substituted heteroaryl, or optionally substituted heterocyclo. In some embodiments, the alkenyl is substituted with a carboxyalkyl group, e.g., -C(=O)OCH2CH3. In some embodiments, the alkenyl is substituted with an optionally substituted phenyl, e.g., 4- (trifluoromethyl)phenyl .

[0219] The term "halo" or "halogen" as used herein by itself or as part of another group refers to -Cl, -F, -Br, or -I.

[0220] The term "nitro" as used herein by itself or as part of another group refers to -NO2.

[0221] The term "cyano" as used herein by itself or as part of another group refers to -CN.

[0222] The term "hydroxy" as herein used by itself or as part of another group refers to -OH.

[0223] 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.

[0224] In one embodiment, the amino is -NH2.

[0225] 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.

[0226] 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.

[0227] 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.

[0228] The term "haloalkyl" as used herein by itself or as part of another group refers to an alkyl substituted by one or more fluorine, chlorine, bromine, and / or iodine atoms. In one embodiment, the alkyl is substituted by one, two, or three fluorine and / or chlorine atoms. In another embodiment, the alkyl is substituted by one, two, or three fluorine atoms. In another embodiment, the alkyl is a Ci-Ce alkyl and the resulting haloalkyl isreferred 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.

[0229] 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.

[0230] 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.

[0231] 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.

[0232] 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.

[0233] 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.

[0234] 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.

[0235] 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.

[0236] 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.

[0237] 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).

[0238] The term "chiral center" or "asymmetric carbon atom" refers to a carbon atom to which four different groups are attached.

[0239] 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.

[0240] The term "racemic" refers to a mixture of equal parts of enantiomers and which mixture is optically inactive.

[0241] 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.

[0242] 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.

[0243] 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.

[0244] 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.

[0245] Salts and solvates, e.g., hydrates, of the Compounds of the Disclosure can also be used in the methods disclosed herein.

[0246] 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.

[0247] 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.

[0248] 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.

[0249] 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.

[0250] 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).

[0251] 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.

[0252] 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 = 0.50 x 100 = 50 wt / wt %). The wt / wt % of a Compound of the Disclosure in a composition comprising 1 kg of the compound, 1 kg natural rubber, 2 kg of synthetic rubber, and 1 kg of carbon black is 20 wt / wt % (1 kg / 5 kg = 0.20 x 100 = 20 wt / wt %). The wt / wt % of natural rubber in a blend of one or more elastomers comprising 20 kg natural rubber and 30 kg synthetic rubber is 40 wt / wt % (20 kg / 50 kg = 0.40 x 100 = 40 wt / wt %).

[0253] 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 % to about 95 wt % of at least one elastomer and from about 5 wt % to about 95 wt% of a Compound of the Disclosure. In some embodiments, the masterbatch comprises about 5 wt %, about 10 wt %, about 15 wt %, about 20 wt %, about 25 wt %, about 30 wt %, about 35 wt %, about 40 wt %, about 45 wt %, about 50 wt %, about 55 wt %, about 60 wt %, about 65 wt %, about 70 wt %, about 75 wt %, about 80 wt %, about 85 wt %, about 90 wt %, or about 95 wt % of a Compound of the Disclosure. In some embodiments, the masterbatch comprises about 5 wt %, about 10 wt %, about 15 wt %, about 20 wt %, about 25 wt %, about 30 wt %, about 35 wt %, about 40 wt %, about 45 wt %, about 50 wt %, about 55 wt %, about 60 wt %, about 65 wt %, about 70 wt %, about 75 wt %, about 80 wt %, about 85 wt %, about 90 wt %, or about 95 wt % of at least one elastomer.

[0254] 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 % to about 95 wt % of a Compound of the Disclosure and from about 5 wt % to about 95 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 %, about 10 wt %, about 15 wt %, about 20 wt %, about 25 wt %, about 30 wt %, about 35 wt %, about 40 wt %, about 45 wt %, about 50 wt %, about 55 wt %, about 60 wt %, about 65 wt %, about 70 wt %, about 75 wt %, about 80 wt %, about 85 wt %, about 90 wt %, or about 95 wt % of a Compound of the Disclosure. In some embodiments, the premix comprises about 5 wt %, about 10 wt %, about 15 wt %, about 20 wt %, about 25 wt %, about 30 wt %, about35 wt %, about 40 wt %, about 45 wt %, about 50 wt %, about 55 wt %, about 60 wt %, about 65 wt %, about 70 wt %, about 75 wt %, about 80 wt %, about 85 wt %, about 90 wt %, or about 95 wt % of at least one additional component, e.g., a filler, a rubber chemical, a plasticizer, an additional anti degradant, or a combination thereof.

[0255] 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

[0256] 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.

[0257] In some embodiments, a Composition of the Disclosure comprises from about 15 wt / wt % to about 85 wt / wt % of a Compound of the Disclosure. In some embodiments, the composition comprises from about 1 wt / wt % to about 5 wt / wt %, from about 1 wt / wt % to about 15 wt / wt %, from about 1 wt / wt % to about 25 wt / wt %, from about 1 wt / wt % to about 35 wt / wt %, from about 1 wt / wt % to about 45 wt / wt %, from about 1 wt / wt % to about 55 wt / wt %, from about 1 wt / wt % to about 65 wt / wt %, from about 1 wt / wt % to about 75 wt / wt %, from about 1 wt / wt % to about 85 wt / wt %, from about 1 wt / wt % to about 95 wt / wt %, from about 5 wt / wt % to about 15 wt / wt %, fromabout 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 about1 wt / wt% to about 7 wt / wt%, from about 1 wt / wt% to about 8 wt / wt%, from about 1 wt / wt% to about 9 wt / wt%, from about 1 wt / wt% to about 10 wt / wt%, from about 1.5 wt / wt% to about 2 wt / wt%, from about 1.5 wt / wt% to about 2.5 wt / wt%, from about 1.5 wt / wt% to about 3 wt / wt%, from about 1.5 wt / wt% to about 3.5 wt / wt%, from about 1.5 wt / wt% to about 4 wt / wt%, from about 1.5 wt / wt% to about 4.5 wt / wt%, from about 1.5 wt / wt% to about 5 wt / wt%, from about 1.5 wt / wt% to about 6 wt / wt%, from about 1.5 wt / wt% to about 7 wt / wt%, from about 1.5 wt / wt% to about 8 wt / wt%, from about 1.5 wt / wt% to about 9 wt / wt%, from about 1.5 wt / wt% to about 10 wt / wt%, from about 2 wt / wt% to about 2.5 wt / wt%, from about 2 wt / wt% to about 3 wt / wt%, from about 2 wt / wt% to about 3.5 wt / wt%, from about 2 wt / wt% to about 4 wt / wt%, from about 2 wt / wt% to about 4.5 wt / wt%, from about 2 wt / wt% to about 5 wt / wt%, from about 2 wt / wt% to about 6 wt / wt%, from about 2 wt / wt% to about 7 wt / wt%, from about 2 wt / wt% to about 8 wt / wt%, from about 2 wt / wt% to about 9 wt / wt%, from about 2 wt / wt% to about 10 wt / wt%, from about 2.5 wt / wt% to about 3 wt / wt%, from about 2.5 wt / wt% to about 3.5 wt / wt%, from about 2.5 wt / wt% to about 4 wt / wt%, from about 2.5 wt / wt% to about 4.5 wt / wt%, from about 2.5 wt / wt% to about 5 wt / wt%, from about 2.5 wt / wt% to about 6 wt / wt%, from about 2.5 wt / wt% to about 7 wt / wt%, from about 2.5 wt / wt% to about 8 wt / wt%, from about 2.5 wt / wt% to about 9 wt / wt%, from about 2.5 wt / wt% to about 10 wt / wt%, from about 3 wt / wt% to about 4 wt / wt%, from about 3 wt / wt% to about 4.5 wt / wt%, from about 3 wt / wt% to about 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 3.5wt / 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.

[0258] In some embodiments, a Composition of the Disclosure comprises about 50 wt / wt % of a Compound of the Disclosure. In some embodiments, the composition comprises about 1 wt / wt %, about 5 wt / wt %, about 10 wt / wt %, about 15 wt / wt %, about 20 wt / wt %, about 25 wt / wt %, about 30 wt / wt %, about 35 wt / wt %, about 40 wt / wt %, about 45 wt / wt %, about 55 wt / wt %, about 60 wt / wt %, about 65 wt / wt %, about 70 wt / wt %, about 75 wt / wt %, about 80 wt / wt %, about 85 wt / wt %, about 90 wt / wt %, or about 95 wt / wt % of a Compound of the Disclosure. In some embodiments, the composition comprises about 0.1 wt / wt%, about 0.5 wt / wt%, about 1 wt / wt%, about 1.5 wt / wt%, about 2 wt / wt%, about 2.5 wt / wt%, about 3 wt / wt%, about 3.5 wt / wt%, about 4 wt / wt%, about 4.5 wt / wt%, about 5 wt / wt%, about 5.5 wt / wt%, about 6 wt / wt%, about 6.5 wt / wt%, about 7 wt / wt%, about 7.5 wt / wt%, about 8 wt / wt%, about 8.5 wt / wt%, about 9 wt / wt%, or about 10 wt / wt% of a Compound of the Disclosure.

[0259] In another embodiment, a Composition of the Disclosure comprises a Compound of the Disclosure and one or more elastomers.

[0260] 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.

[0261] In some embodiments, the natural rubber comprises rubber derived from an alternative rubber plant. The term "natural rubber comprises rubber derived from an alternative rubber plant" as used herein refers to a naturally occurring elastomer that can be obtained from "non-Hevea" sources. In some embodiments, the alternative rubber plant is Parthenium argentatum (guayule) or Taraxacum kok-saghyz (Russian dandelion).

[0262] 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.

[0263] 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 45 wt / wt % to about 100 wt / wt %, from about 55 wt / wt % to about 65 wt / wt %, from about 55 wt / wt % to about 75 wt / wt %, from about 55 wt / wt % to about 85 wt / wt %, from about 55 wt / wt % to about 95 wt / wt %, from about 55 wt / wt % to about 100 wt / wt %, from about 65 wt / wt % to about 75 wt / wt %, from about 65 wt / wt % to about 85 wt / wt %, from about 65 wt / wt % to about 95 wt / wt %, from about 65 wt / wt % to about 100 wt / wt %,from about 75 wt / wt % to about 85 wt / wt %, from about 75 wt / wt % to about 95 wt / wt %, from about 75 wt / wt % to about 100 wt / wt %, from about 85 wt / wt % to about 95 wt / wt %, or from about 95 wt / wt % to about 100 wt / wt % of one or more elastomers.

[0264] 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.

[0265] 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.

[0266] In some embodiments, a Composition of the Disclosure comprises from about 1 phr to about 5 phr of a Compound of the Disclosure. In some embodiments, the composition comprises from about 0.01 phr to about 0.1 phr, from about 0.01 phr to about 0.5 phr, from about 0.01 phr to about 1 phr, from about 0.01 phr to about 2 phr, from about 0.01 phr to about 3 phr, from about 0.01 phr to about 4 phr, from about 0.01 phr to about 5 phr, from about 0.01 phr to about 7.5 phr, from about 0.01 phr to about 10 phr, from about 0.01 phr to about 20 phr, from about 0.1 phr to about 0.5 phr, from about 0.1 phr to about 1 phr, from about 0.1 phr to about 2 phr, from about 0.1 phr to about 3 phr, from about 0.1 phr to about 4 phr, from about 0.1 phr to about 5 phr, from about 0.1 phr to about 7.5 phr, from about 0.1 phr to about 10 phr, from about 0.1 phr to about 20 phr, from about 1 phr to about 2 phr, from about 1 phr to about 3 phr, from about 1 phr to about 4 phr, from about 1 phr to about 7.5 phr, from about 1 phr to about 10 phr, from about 1 phr to about 20 phr, from about 2 phr to about 3 phr, from about 2 phr to about 4 phr, from about 2 phr to about 5 phr, from about 2 phr to about 7.5 phr, from about 2 phr to about 10 phr, from about 2 phr to about 20 phr, from about 3 phr to about 4 phr, from about 3 phr to about 5 phr, from about 3 phr to about 7.5 phr, from about 3 phr to about 10 phr, from about 3 phr to about 20 phr, from about 4 phr to about 5 phr, from about 4 phr to about 7.5 phr, from about 4 phr to about 10 phr, from about 4 phr to about 20 phr, from about 5 phr to about 7.5 phr, from about 5 phr to about 10 phr, from about 5 phr toabout 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.

[0267] 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.

[0268] In some embodiments, a Composition of the Disclosure comprises a Compound of the Disclosure and one or more fillers.

[0269] 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.

[0270] In some embodiments, the filler is derived from natural sources. For example, silica may be derived from rice husks.

[0271] In some embodiments, a Composition of the Disclosure comprises from about15 wt / wt % to about 85 wt / wt % of one or more fillers. In some embodiments, the composition comprises from about 1 wt / wt % to about 5 wt / wt %, from about 1 wt / wt % to about 15 wt / wt %, from about 1 wt / wt % to about 25 wt / wt %, from about 1 wt / wt % to about 35 wt / wt %, from about 1 wt / wt % to about 45 wt / wt %, from about 1 wt / wt % to about 55 wt / wt %, from about 1 wt / wt % to about 65 wt / wt %, from about 1 wt / wt % to about 75 wt / wt %, from about 1 wt / wt % to about 85 wt / wt %, from about 1 wt / wt % to about 95 wt / wt %, from about 5 wt / wt % to about 15 wt / wt %, from about 5 wt / wt % to about 25 wt / wt %, from about 5 wt / wt % to about 35 wt / wt %, from about 5 wt / wt % to about 45 wt / wt %, from about 5 wt / wt % to about 55 wt / wt %, from about 5 wt / wt % to about 65 wt / wt %, from about 5 wt / wt % to about 75 wt / wt %, from about 5 wt / wt % to about 85 wt / wt %, from about 5 wt / wt % to about 95 wt / wt %, from about 15 wt / wt % to about 25 wt / wt %, from about 15 wt / wt % to about 35 wt / wt %, from about 15 wt / wt % to about 45 wt / wt %, from about 15 wt / wt % to about 55 wt / wt %, from about 15 wt / wt % to about 65 wt / wt %, from about 15 wt / wt % to about 75 wt / wt %, from about 15 wt / wt % toabout 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.

[0272] 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.

[0273] 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, fromabout 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.

[0274] 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.

[0275] 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.

[0276] The term "vulcanization" as used herein refers to a process wherein cross-links are formed between elastomers to effect changes in the material properties of elastomers. In particular, vulcanization typically increases the rigidity and durability of elastomers. Vulcanization is carried out at room temperature or at elevated temperatures, depending on the nature of the elastomer(s), filler(s), and rubber chemical(s) being used. The term "curing" is also used in the art to describe this process.

[0277] 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.

[0278] 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 benzothiazole sulfenamide (OBTS), V-oxy di ethylenethiocarbamyl-V'-oxy di ethylene sulfenamide (OTOS), and thiocarbamyl sulfenamide. Non-limiting examples of thiurams include dimethylcarbamothioic dithioperoxyanhydride (thiram), dipentamethylene thiuram tetrasulfide (DPIT), tetrabenzyl thiuram disulfide (TBzTD), tetraethylthiuram disulfide(TETD), tetramethylthiuram disulfide (TMTD), and tetramethylthiuram monosulfide (TMTM). Non-limiting examples of dithiocarbamates include zinc dimethyldithiocarbamate (ZDMC), zinc diethyldithiocarbamate (ZDEC), zinc dibutyl di thiocarbamate (ZDBC), nickel dibutyl dithiocarbamate (NDBC), sodium dibenzyldithiocarbamate (SBEC), sodium diethyldithiocarbamate (SDEC), tellurium diethyldithiocarbamate (TDEC), and zinc dibenzyldithiocarbamate (ZEBC).

[0279] 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.

[0280] 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.

[0281] In some embodiments, a Composition of the Disclosure comprises from about15 wt / wt % to about 85 wt / wt % of one or more rubber chemicals. In some embodiments, the composition comprises from about 1 wt / wt % to about 5 wt / wt %, from about 1 wt / wt % to about 15 wt / wt %, from about 1 wt / wt % to about 25 wt / wt %, from about 1 wt / wt % to about 35 wt / wt %, from about 1 wt / wt % to about 45 wt / wt %, from about 1 wt / wt % to about 55 wt / wt %, from about 1 wt / wt % to about 65 wt / wt %, from about 1 wt / wt % to about 75 wt / wt %, from about 1 wt / wt % to about 85 wt / wt %, from about 1 wt / wt % to about 95 wt / wt %, from about 5 wt / wt % to about 15 wt / wt %, from about 5 wt / wt % to about 25 wt / wt %, from about 5 wt / wt % to about 35 wt / wt %, from about 5 wt / wt % to about 45 wt / wt %, from about 5 wt / wt % to about 55 wt / wt %, from about 5 wt / wt % to about 65 wt / wt %, from about 5 wt / wt % to about 75 wt / wt %, from about 5 wt / wt % to about 85 wt / wt %, from about 5 wt / wt % to about 95 wt / wt %, from about 15 wt / wt % to about 25 wt / wt %, from about 15 wt / wt % to about 35 wt / wt %, from about 15 wt / wt % toabout 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.

[0282] 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.

[0283] In some embodiments, a Composition of the Disclosure comprises from about 1 phr to about 20 phr of one or more rubber chemicals. In some embodiments, the composition comprises from about 0.1 phr to about 1 phr, from about 0.1 phr to about 5 phr, from about 0.1 phr to about 10 phr, from about 0.1 phr to about 15 phr, from about 0.1 phr to about 20 phr, from about 0.1 phr to about 25 phr, from about 0.1 phr to about 30 phr, from about 0.1 phr to about 35 phr, from about 0.1 phr to about 40 phr, from about 1 phr to about 5 phr, from about 1 phr to about 10 phr, from about 1 phr to about 15 phr, from about 1 phr to about 25 phr, from about 1 phr to about 30 phr, from about 1 phrto 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.

[0284] 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.

[0285] 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.

[0286] In some embodiments, a Composition of the Disclosure comprises from about15 wt / wt % to about 85 wt / wt % of one or more plasticizers. In some embodiments, the composition comprises from about 1 wt / wt % to about 5 wt / wt %, from about 1 wt / wt % to about 15 wt / wt %, from about 1 wt / wt % to about 25 wt / wt %, from about 1 wt / wt % to about 35 wt / wt %, from about 1 wt / wt % to about 45 wt / wt %, from about 1 wt / wt % to about 55 wt / wt %, from about 1 wt / wt % to about 65 wt / wt %, from about 1 wt / wt % to about 75 wt / wt %, from about 1 wt / wt % to about 85 wt / wt %, from about 1 wt / wt % to about 95 wt / wt %, from about 5 wt / wt % to about 15 wt / wt %, from about 5 wt / wt % to about 25 wt / wt %, from about 5 wt / wt % to about 35 wt / wt %, from about 5 wt / wt % to about 45 wt / wt %, from about 5 wt / wt % to about 55 wt / wt %, from about 5 wt / wt % 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 plasticizers.

[0287] 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.

[0288] 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.

[0289] 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.

[0290] In some embodiments, a Composition of the Disclosure further comprises one or more additional anti degradants that is not a Compound of the Disclosure. In some embodiments, the one or more additional anti degradants is an antioxidant. In some embodiments, the one or more additional anti degradants is an antiozonant. Non-limiting examples of anti degradants include paraphenylenediamines (PPDs), trimethyldihydroquinolines (TMQs), phenolics, alkylated diphenylamines (DP As), diphenylamineketone condensates, and natural anti degradants. Non-limiting examples of PPDs include 7V1-(4-methylpentan-2-yl)-A4-phenylbenzene- 1 ,4-diamine (6PPD), N-( 1 ,4- dimethylpentyl)- '-phenyl-p-phenylenediamine (7PPD), A1-phenyl-7V4-(propan-2- yl)benzene-l,4-diamine (IPPD), A( '-di -scc-butyl - -phenylenedi amine (44PD), N,N'~ bis(l,3-dimethylbutyl)-p-phenylenediamine (66PD), 7V,A-bis(l,4-dimethylpentyl)-p- phenylenediamine (77PD), and N-N'-dioctyl- -phenylenediamine (88PD). Non-limitingexamples of TMQs include 2,2,4-trimethyl-l,2-dihydroquinoline and oligomers or polymers thereof.

[0291] 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 %, from about 55 wt / wt % to about 95 wt / wt %, from about 65 wt / wt % to about 75 wt / wt %, from about 65 wt / wt % to about 85 wt / wt %, from about 65 wt / wt % to about 95 wt / wt %, from about 75 wt / wt % to about 85 wt / wt %, from about 75 wt / wt % to about 95 wt / wt %, or from about 85 wt / wt % to about 95 wt / wt % of one or more additional anti degradants.

[0292] 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.

[0293] 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.

[0294] 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.

[0295] In some embodiments, the disclosure provides a composition comprising a Compound of the Disclosure and one or more carriers. The term "carrier" as used herein refers to a solid that can adsorb a liquid while retaining the general properties of a solid at room temperature. In some embodiments, the carrier is an inert material. In some embodiments, the carrier has a high surface area. In some embodiments, the carrier comprises particles with diameters of less than 500 microns.

[0296] 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.

[0297] 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.

[0298] 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.

[0299] 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.

[0300] 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.

[0301] 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.

[0302] In some embodiments, the present disclosure provides a composition recited in Table 3.Table 3

[0303] In some embodiments, the vulcanized tire or other rubber article composition of Table 3 comprises about 0.1 wt %, about 0.2 wt %, about 0.3 wt %, about 0.4 wt %, about 0.5 wt %, about 0.6 wt %, about 0.7 wt %, about 0.8 wt %, about 0.9 wt %, about 1 wt %, about 2 wt %, about 3 wt %, about 4 wt %, about 5 wt %, about 6 wt %, about 7 wt %, about 8 wt %, about 9 wt %, or about 10 wt % of a Compound of the Disclosure. In some embodiments, the vulcanized tire or other rubber article of Table 3 comprises comprises about 5 wt %, about 10 wt %, about 15 wt %, about 20 wt %, about 25 wt %, about 30 wt %, about 35 wt %, about 40 wt %, about 45 wt %, about 50 wt %, about 55 wt %, about 60 wt %, about 65 wt %, about 70 wt %, about 75 wt %, about 80 wt %, about 85 wt %, about 90 wt %, or about 95 wt % of at least one elastomer.

[0304] In some embodiments, the unvulcanized in-tire component or built up component or other end use component composition of Table 3 comprises about 0.01 wt %, about 0.02 wt %, about 0.03 wt %, about 0.04 wt %, about 0.05 wt %, about 0.06 wt %, about 0.07 wt %, about 0.08 wt %, about 0.09 wt %, about 0.1 wt %, about 0.2 wt %, about 0.3 wt %, about 0.4 wt %, about 0.5 wt %, about 0.6 wt %, about 0.7 wt %, about 0.8 wt %,about 0.9 wt %, about 1 wt %, about 2 wt %, about 3 wt %, about 4 wt %, about 5 wt %, about 6 wt %, about 7 wt %, about 8 wt %, about 9 wt %, or about 10 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 3 comprises comprises about 5 wt %, about 10 wt %, about 15 wt %, about 20 wt %, about 25 wt %, about 30 wt %, about 35 wt %, about 40 wt %, about 45 wt %, about 50 wt %, about 55 wt %, about 60 wt %, about 65 wt %, about 70 wt %, about 75 wt %, about 80 wt %, about 85 wt %, about 90 wt %, or about 95 wt % of at least one elastomer.Vulcanized Elastomeric Articles

[0305] 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.

[0306] The present disclosure also provides vulcanized elastomeric articles prepared using a composition described herein.

[0307] 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.

[0308] 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.

[0309] In some embodiments, the vulcanized elastomeric article is a rubber overshoe, a sealing strip, an acoustic panel, an air spring, a bellow, a membrane, a tactile sensor, a crash pad, a hose, a conveyor belt, or a flooring.Processes

[0310] 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.

[0311] In some embodiments, the vulcanizing is performed at an average temperature of from about 140 °C to about 160 °C. In some embodiments, the vulcanizing is performed at an average temperature of from about 80 °C to about 100 °C, from about 80 °C to about 120 °C, from about 80 °C to about 140 °C, from about 80 °C to about 160 °C, from about 80 °C to about 180 °C, from about 80 °C to about 200 °C, from about 100 °C to about 120 °C, from about 100 °C to about 140 °C, from about 100 °C to about 160 °C, from about 100 °C to about 180 °C, from about 100 °C to about 200 °C, from about 120 °C to about 140 °C, from about 120 °C to about 160 °C, from about 120 °C to about 180 °C, from about 120 °C to about 200 °C, from about 140 °C to about 180 °C, from about 140 °C to about 200 °C, from about 160 °C to about 180 °C, from about 160 °C to about 200 °C, or from about 180 °C to about 200 °C.

[0312] 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.

[0313] 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

[0314] 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 A-(furan-2-ylmethyl)-2,2,4-trimethyl-l,2-dihydroquinolin-6-amine (Compound 1)Step 1

[0315] To a 500-mL flask fitted with an overhead mechanical stirrer, a 50-mL pressure- equalized addition funnel, and a thermometer was loaded 1,4-phenylenediamine (20.9 g; 180 mmol) and methanol (150 mL). The mixture was stirred under N2 protection. A solution of furfural (15.0 g; 12.9 mL; 155.7 mmol) in methanol (19 mL) was loaded to the addition funnel. Once 1,4-phenylenediamine was fully dissolved, the solution of furfural was gradually added to the flask over 8-10 minutes. After completion of the addition, the reaction mixture was stirred at room temperature for 30 minutes (formation of the imine intermediate). The flask was chilled with an ice-water bath. Sodium borohydride (7.4 g; 195 mmol) was added portionwise such that the temperature was kept below 35 °C. About 30 min later, the ice-water bath was removed. The reaction mixture was stirred without external cooling or heating for 90 minutes (reduction of imine to desired amine product). DI water (150 mL) was slowly added to the flask to quench the reaction. Once the exotherm subsided, the mixture was transferred to a 1-L beaker equipped with a stirbar. Ethyl acetate (400 mL) was added. The two-phase system was vigorously stirred, then transferred to a 1-L separatory funnel. The aqueous layer was discarded. The organic layer was washed with water (100 mL) and aqueous saturated NaCl (50 mL), then stripped of volatiles under reduced pressure (rotary evaporator; water bath = 50 °C). The crude product was diluted with toluene (10 mL). The obtained solution was loaded to a column (73 mm inner diameter) prepared with silica gel 60 (20 cm height) and 50% ethyl acetate in hexanes. The column was eluted with 50% ethyl acetate in hexanes. Each fraction coming out was analyzed by silica gel TLC (50% ethyl acetate in hexanes). The fractions containing the dot at Rf = 0.8 were discarded (over-alkylated by-product N1, N4-bis(furan-2-ylmethyl)benzene- l ,4-diamine). Next, the fractions containing the dot at Rf = 0.4 were collected, combined, then stripped of volatiles under reduced pressure (rotary evaporator; water bath = 50 °C). Further drying on the rotary evaporator (50 °C; < 3 mbars) for 30 minutes afforded N1-(furan-2-ylmethyl)benzene-l,4-diamine (Intermediate Compound 1-1) a dark reddish liquid (18.3 g; 83% yield with respect to furfural). The desired structure was authenticated by13C NMR spectroscopy, as shown in Fig. 1.Step 2

[0316] To a 250-mL flask fitted with a stir-bar and a reflux condenser was loaded N1- (furan-2-ylmethyl)benzene-l,4-diamine (Intermediate Compound 1-1; 15.367 g; 81.64 mmol), and acetone dried over molecular sieves (25.0 mL; 338 mmol). The mixture was stirred under N2 protection and immerged in an oil bath at room temperature. Zinc(II) triflate (3.0139 g; 8.29 mmol) was loaded in one portion. The reaction mixture was heated (oil bath temperature = 61 °C) for 6.5 hours, then allowed to cool to room temperature overnight. Again, the reaction mixture was heated (oil bath temperature = 61 °C) for 6.5 hours, then allowed to cool to room temperature. Additional acetone dried over molecular sieves (10 mL; 135.5 mmol) was added. The reaction mixture was stirred at room temperature overnight, then heated (oil bath temperature = 61 °C) for 6.5 hours. The total reflux time was 19.5 hours. Upon cooling to room temperature (2 days), the crude material was loaded into a 73 mm inner diameter column prepared with silica gel 60 (70-230 mesh; 29 cm height) and 20% ethyl acetate in hexanes. Minute amounts of acetone were used to rinse the flask and the washes were loaded to the column. The column was eluted with 20% ethyl acetate in hexanes. Each fraction coming out was analyzed by silica gel TLC (20% ethyl acetate in hexanes). Once the desired product started coming out (Rf = 0.5), the column was eluted with 50% ethyl acetate in hexanes. All the fractions containing the dot at Rf = 0.5 (20% ethyl acetate in hexanes) were combined and stripped of volatiles under reduced pressure (rotary evaporator; water bath = 50 °C). The resulting yellow oil was dried on the rotary evaporator (50 °C; < 10 mbars)for 1.5 hour to yield = 13.7 g (62.5% with respect to Nl-(furan-2-ylmethyl)benzene-l,4- diamine) of A-(furan-2-ylmethyl)-2,2,4-trimethyl-l,2-dihydroquinolin-6-amine (Compound 1) as a yellow oil. Compound 1 was characterized byJH and13C NMR spectroscopy, as shown in Figs. 2 and 3, respectively. LC-UV analysis indicated 94.1% purity at 260 nm detection.EXAMPLE 2Synthesis of diethyl 2-methyl-6-(phenylamino)-l,2-dihydroquinoline-2,4-dicarboxylate (Compound 3)

[0317] To a 250-mL round bottom flask fitted with a stir-bar and a reflux condenser was loaded N1-phenylbenzene- 1,4-diamine (4-ADPA; 14.6 g; 79.2 mmol) and acetonitrile (85 mL). The mixture was stirred under N2 protection. Once 4-ADPA was fully dissolved, ethyl pyruvate (18.5 mL; 166 mmol) and iodine (0.623 g; 2.45 mmol) were sequentially added to the flask. The solution turned darker upon addition of iodine. The mixture was heated (oil bath temperature set to 60 °C). The temperature was maintained for about 2 h. Upon cooling to room temperature, sodium sulfite (2.4 g; 19.0 mmol) was added and the mixture was stirred for about 2 h. The volatiles were stripped under reduced pressure (rotary evaporator; water bath = 50 °C). The crude material was diluted with toluene (16 mL). The obtained solution was loaded to a column (73 mm inner diameter) previously prepared with silica gel 60 and 30% ethyl acetate in hexanes. The height of silica gel in the column was approx. 24 cm. The column was eluted with 30% ethyl acetate in hexanes. Each fraction coming out was analyzed by silica gel TLC (30% ethyl acetate in hexanes). The fractions containing the dot at Rf = 0.5 were collected, combined, and stripped of their volatiles under reduced pressure (rotary evaporator; water bath = 50 °C). Drying on the rotary evaporator (55 °C; < 8 mbars) for approx. 1 hour afforded 20.0 g of diethyl 2-methyl-6-(phenylamino)-l,2-dihydroquinoline-2,4-dicarboxylate (Compound 3) as a dark-red viscous oil (66% yield with respect to 4-ADPA). Compound 3 wascharacterized byJH and13C APT NMR spectroscopy, as shown in Figs. 4 and 5, respectively. LC-UV analysis indicated 98.4% purity at 260 nm detection.EXAMPLE 3Synthesis of 2,4-diethyl-2-methyl-7V-phenyl-l,2-dihydroquinolin-6-amine (Compound 6)

[0318] To a 250-mL round bottom flask equipped with a stir-bar and reflux condenser was loaded 4-ADPA (5.08 g; 27.6 mmol) and methyl ethyl ketone (40 mL; 447 mmol). The mixture was stirred under N2 protection. Zinc(II) tritiate (1.005 g; 2.77 mmol) was added and the reaction mixture was refluxed (oil bath set to 80 °C) for 14 hours. A first purification by column chromatography (silica gel 60; 20% ethyl acetate in hexanes) allowed removal of most of the impurities. Then a second column chromatography (silica gel 60; 10% ethyl acetates in hexanes to 20% ethyl acetate in hexanes gradient) was carried out to obtain a product in acceptable purity. LC-UV analysis indicated 95.0% purity at 260 nm detection.Alternative Procedure

[0319] A mixture of of 4-ADPA (30 g; 163 mmol), methyl ethyl ketone (75 mL; 838 mmol), and zinc(II) tritiate (6.0 g; 16.5 mmol) was refluxed under N2 blanket overnight. Upon cooling temperature, the mixture post reaction was purified by column chlromatography over silica gel using 10-20% AcOEt in hexanes as the eluent. After stripping of the volatiles under reduced pressure, the purified Compound 6 was obtained. The structure was authenticated by13C APT NMR spectroscopy (THF-ds), as shown in Fig. 6.EXAMPLE 4Synthesis of 2,2,4,7,7,9-hexamethyl-l,2,6,7-tetrahydropyrido[2,3-g]quinoline (Compound Bl)Compound B1

[0320] To a 250-mL flask fitted with a stir-bar and a reflux condenser were loaded 1,4- phenylenediamine (12.6 g; 117 mmol) and acetone dried over molecular sieves (57 mL; 771 mmol). The mixture was stirred under N2 protection. Most of 1,4-phenylenediamine remained insoluble. The flask was immersed in an oil bath at room temperature. Zinc(II) tritiate (4.5039 g; 12.4 mmol) was loaded in one portion. Most of the solids dissolved readily. The reaction mixture was refluxed (oil bath temperature = 63 °C) for 26 hours (some insoluble yellow material separated). Upon cooling to room temperature, the mixture was partitioned between di chloromethane (250 mL) and DI water (100 mL) in a separatory funnel. After shaking and decanting, the aqueous phase was discarded. The organic phase was washed with DI water (2 x 100 mL) and saturated aqueous NaCl (100 mL), then stripped of volatiles under reduced pressure (rotary evaporator; water bath = 45 °C). The crude material was dissolved in di chloromethane (100 mL). The obtained solution (some insoluble material remained) was carefully charged into a sintered filter (7.2 cm inner diameter) previously prepared with silica gel (high purity; 60 A; 230-400 mesh; 40-63 pm; approx. 7.0 cm height dry) and eluent (70% dichloromethane - 25% hexanes - 5% ethyl acetate). The filter was gravimetrically eluted with additional eluent. The colored filtrate was collected (approx. 700 mL) and stripped of volatiles under reduced pressure (rotary evaporator; water bath = 45 °C). The obtained solid was dried on the rotary evaporator (water bath = 45 °C; < 5 mbars) for 15 min to yield 10.3 g (33% with respect to 1,4-phenylenediamine) of 2,2,4,7,7,9-hexamethyl-l,2,6,7- tetrahydropyrido[2,3-g]quinoline (Compound Bl) as a yellow solid. Compound Bl was characterized byJH and13C APT NMR spectroscopy, as shown in Figs. 7 and 8, respectively. LC-UV analysis indicated 91.9% purity at 260 nm detection.EXAMPLE 5Synthesis of 2,2,4,7,7,9-hexamethyl-l,2,3,4,6,7,8,9-octahydropyrido[2,3-g]quinoline (CompoundB2)Ethyl acetate10% Pd / C cat. Pressurized H2room temperatureCompound B1 Compound B2

[0321] To a 300-mL Parr autoclave was loaded Compound Bl (3.0 g; 11.2 mmol), ethyl acetate (100 mL), and 10% Pd on C (Sigma; 0.61 g). The reaction mixture was stirred at room temperature under pressurized Eb (50 PSIG) for 35 minutes. The mixture post reaction was filtered under suction through Celite S and the cake was rinsed with copious amounts of ethyl acetate. The combined filtrates were stripped of their volatiles under reduced pressure (rotary evaporator; water bath = 50 °C) to yield 2,2,4,7,7,9-hexamethyl- l,2,3,4,6,7,8,9-octahydropyrido[2,3-g]quinoline (Compound B2) as a light-brown solid weighing 2.1 g. Compound B2 was characterized byJH and13C APT NMR spectroscopy, as shown in Figs. 9 and 10, respectively. LC-UV analysis indicated 93.1% purity at 260 nm detection as a mixture of diastereomers.EXAMPLE 6

[0322] To a 250-mL round bottom flask fitted with a stir-bar was loaded 2,2,4-trimethyl- N-phenyl-l,2-dihydroquinolin-6-amine (5.0 g; 18.9 mmol). The flask was put under N2 protection and dry DMF (27 mL) was added. Stirring was started. Once 2,2,4-trimethyl- N-phenyl-l,2-dihydroquinolin-6-amine was fully disolved, anhydrous potassium carbonate (3.317 g; 24.0 mmol) was added. The flask was cooled with a cold tap water bath. lodomethane (1.5 mL; 24.0 mmol) was added over 1-2 minutes. No noticeable exotherm occurred. The cooling bath was removed. The reaction mixture was stirredwithout external cooling or heating for 21.5 hours. Deionized water (27 mL) was added and the mixture was stirred for 30 minutes. AcOEt (100 mL) and deionized water (20 mL) were added and the mixture was stirred until dissolution of the gummy material. The obtained 2-phase system was transferred to a separatory funnel and the organic layer was collected. The aqueous layer was extracted with AcOEt (70 mL). The combined organic layers were washed with aqueous 1 mol / L NaOH (3 x 50 mL) and aqueous NaCl, dried over MgSO4, filtered, then stripped of volatiles under reduced pressure (rotary evaporator; water bath = 50 deg C). Further drying on the rotary evaporator (60 deg C; < 10 mbars; 1 hour) afforded the crude material (brown oil; 4.1 g). The crude material was dissolved in 5% AcOEt in hexanes (7 mL). The obtained solution was loaded into a 41 mm inner diameter column prepared with silica gel 60 and 5% AcOEt in hexanes. The height of silica gel in the column was 25-26 cm. The column was eluted with 5% AcOEt in hexanes. Each portion coming out was analyzed by silica gel TLC. Fraction 1 containing the material having a Rf of 0.4 (5% AcOEt in hexanes) was collected. The column was eluted with 20% AcOEt in hexanes. Fraction 2 containing the material having a Rf of 0.15 (5% AcOEt in hexanes) was collected. Each fraction was independently stripped of volatiles under reduced pressure (rotary evaporator; water bath = 50 deg C). Further drying on the rotary evaporator (60 deg C; 9-10 mbars) until constant weight afforded the final products.

[0323] Compound (33) (Fraction 1; chemical name: N, 1,2,2, 4-pentamethyl-N-phenyl- 1,2- dihydroquinolin-6-amine; isolated yield = 0.8 g; light yellow oil; LC-UV purity = 99.0 area% at 260 nm detection. The structure was authenticated by LC-MS (M+l = 293.2), as well as carbon 13 APT NMR spectroscopy (Fig 11).

[0324] Compound (32) (Fraction 2; chemical name: l,2,2,4-tetramethyl-N-phenyl-l,2- dihydroquinolin-6-amine; isolated yield = 3.2 g; light yellow oil; LC-UV purity = 95.5 area% at 260 nm detection. The structure was authenticated by LC-MS (M+l = 279.2), as well as carbon 13 APT NMR spectroscopy (Fig. 12).EXAMPLE 7Synthesis of Compound (26)

[0325] To a stirred solution of 4-amino-diphenylamine (100.0 g, 0.543 mol) in toluene (600 mL) was added 2-methylbut-3-yn-2-ol (73.1 g, 0.869 mol) at RT. The reaction mixture was purged with nitrogen for 10-15 min, followed by the addition of CuCh (7.3 g, 0.054 mol) and CuCl (5.3 g, 0.065 mol). The resulting reaction contents were heated to 110-115 °C and stirred for 6 h. After completion of reaction (monitored by TLC) was cooled to RT, filtered through celite, the bed washed with toluene (300 mL), evaporated the collected filtrate under vacuum to afford 128 g of residue, which was dissolved in minimum quantity of toluene and loaded on silica gel (100-220 mesh) where it was eluted with 7-10% ethyl acetate in hexane to afford 32 g of crude compound as dark brown solid. The solid was suspended in 5% IP A in hexane (100 mL), stirred for 16 h, filtered and dried under vacuum to afford 21.1 g of Compound (26) as a pale yellow solid (>95% purity by HPLC 260 nm, Mass (m / z): 251.14 [M+H]+)

[0326] 'HNMR (400 MHz, DMSO-t / 6): 5 7.41 (s, 1H), 7.08 (dd, J= 8.0, 3.2 Hz, 1H), 6.75 (d, J= 8.0 Hz, 2H), 6.68 (dd, J= 8.0, 2.4 Hz, 1H), 6.64 (d, J= 2.4 Hz, 1H), 6.59 (t, J= 7.2 Hz, 1H), 6.40 (d, J= 8.0 Hz, 1H), 6.17 (d, J= 9.6 Hz, 1H), 5.58 (s, 1H), 5.44 (dd, J= 9.6, 1.6 Hz, 1H), 1.21 (s, 6H)

[0327] 13C NMR (100 MHz, DMSO-t / 6): 5 147.20, 140.15, 131.94, 131.74, 129.42, 123.76, 122.81, 120.30, 120.06, 117.41, 114.13, 113.30, 51.88, 31.01EXAMPLE 8Synthesis of Compound (34)

[0328] To nitrogen degassed toluene (300 mL) was added Pd2(dbas) (4.35 g, 0.0047 mol) and X-phos (1.13 g, 0.002 mol) at RT. The solution was degassed with additional nitrogen for an additional 30 minutes. Then reaction contents were heated to 60 °C and stirred for 20 min, followed by the addition of 6-bromo-2,2,4-trimethyl-l,2- dihydroquinoline (30.0 g, 0.12 mol), N-Methyl aniline (14.3 mL,0.13 mol) and NaOtBu (17.15 g, 0.17 mol). The resulting reaction mixture was heated at 90°C and stirred for 16 h. After completion of the reaction (monitored by TLC), the mixture was cooled to RT, filtered through celite bed. The bed was washed with EtOAc (500mL). Solvent was evaporated under reduced pressure at 45 °C to get 45.0 g of crude product. The reaction was repeated to afford a combined 75.0 g of crude product. The crude product was purified by column chromatography using silica gel (60-120mesh) as the stationary phase, eluting with 1% ethyl acetate in hexane. The collected pure fractions were evaporated under vacuum to afford 45.0 g of Compound (34) as a brown oil (>98% pure by HPLC 260 nm, Mass (m / z): 279.1 [M+H]+).

[0329] 'HNMR (400 MHz, DMSO-t / 6): 5 7.11 (t, J=2.4 Hz, 2H), 6.75-6.71 (m, 2H), 6.62-6.59 (m, 3H), 6.47 (d, J=8.4 Hz, 1H), 5.85 (s, 1H), 5.29 (s, 1H), 3.12 (s, 3H), 1.83 (s, 3H), 1.21 (s, 6H).

[0330] 13C NMR (100 MHz, DMSO-t / 6): 5 150.46, 142.36, 137.17, 129.12, 127.73, 127.14, 122.01, 121.48, 116.88, 113.85, 113.53, 51.70, 31.41, 18.68EXAMPLE 9Synthesis of Compound (35)

[0331] To a 250 mL round-bottom flask equipped with a stir bar was added 2,2,4- trimethyl-N-phenyl-l,2-dihydroquinolin-6-amine (40.0 g, 1 Eq, 151 mmol) and acetic anhydride (17.0 g, 15.7 mL, 1.1 Eq, 166 mmol). The reaction was sealed with a septum and allowed to stir at 90 °C for 5 hours. After this time, the reaction was diluted with 200 mL of EtOAc and transferred to a separatory funnel. The organic layer was washed with saturated aq. NaHCOs (3x100 mL), water (2x100 mL), and brine (50 mL) before drying over Na2SO4. The organic layer was concentrated by rotary evaporation and subsequentlyrecrystallized in methanol. The resulting solid was isolated by vacuum filtration, washing with cold methanol, and dried under high-vacuum to afford the desired Compound (35) as a white powder (41.086 g, 134.09 mmol, 88.6 %). Product is 97.2% by HPLC 260nm. NMR obtained in DMSO-t / 6

[0332] 'HNMR (81 MHz): 5 7.56 - 7.19 (m, 5H), 6.88 (d, J = 6.7 Hz, 2H), 6.44 (d, J = 8.8 Hz, 1H), 6.04 (s, 1H), 5.30 (s, 1H), 1.92 (s, 3H), 1.88 - 1.75 (m, 3H), 1.20 (s, 6H).

[0333] 13C NMR (20 MHz): 5 169.73, 143.73, 143.22, 131.15, 128.78, 128.04, 126.93,126.65, 126.64, 125.85, 122.94, 120.30, 112.37, 51.27, 31.13, 23.27, 18.13.EXAMPLE 10Synthesis of Compound (36)

[0334] To a 500 mL round-bottom flask equipped with a stir bar was added 2,2,4- trimethyl-N-phenyl-l,2-dihydroquinolin-6-amine (50.00 g, 1 Eq, 189.1 mmol) and Pyridine (100.0 mL). The reaction was allowed to stir at 0 °C for 20 minutes before 4- methylbenzenesulfonyl chloride (37.14 g, 1.03 Eq, 194.8 mmol) was slowly added portion-wise over the course of 20 minutes. The reaction was allowed to warm to room temperature and stirred for 4 hours. After this time, the reaction was diluted with 200 mL of EtOAc and poured into a separatory funnel. The organic layer was washed with water (2x100 mL), saturated aqueous NaHCCh (2x100 mL), water (1x100 mL), and brine (1x50 mL). The organic layer was allowed to dry over Na2SO4 before concentrating by rotary evaporation. The resulting dark brown oil was triturated with boiling methanol to liberate a powder which was collected by vacuum filtration, washing with ice-cold methanol. The solid was dried under high-vacuum to afford Compound (36) as a white (49.24 g, 118 mmol, 62.2 %) Product is 98.9% pure by HPLC 260nm. NMR obtained in DMSO-t / 6.

[0335] 1H NMR (81 MHz): 5 7.76-7.16 (m, 9H), 6.93-6.64 (m, 1H), 6.40 (d, J=8.3 Hz, 1H), 6.14 (s, 1H), 5.30 (s, 1H), 2.40 (s, 3H), 2.02-1.71 (s, 3H), 1.21 (s, 6H)

[0336] 13C NMR (20 MHz): 5 144.17, 143.73, 142.51, 137.59, 129.94, 129.79, 129.43,129.05, 128.43, 127.79, 127.42, 126.99, 126.89, 124.42, 120.25, 112.53, 51.76, 31.50, 21.26, 18.16EXAMPLE 11Synthesis of Compound (42)Compound (42)

[0337] A solution of 4-amino-diphenylamine (100.0 g, 0.543 mol) in acetone (500 mL) was purged with nitrogen for 30 min, followed by the addition of zinc tritiate (39.4 g, 0.108 mol), under nitrogen atmosphere at RT. The resulting reaction mixture was heated at 75-80°C and stirred for 16 h. After completion of reaction, (monitored by TLC), the system was cooled to room temperature and partitioned between ethyl acetate (500 mL) and water (250 mL). The organic layer was separated and washed with saturated sodium bicarbonate solution (250 mL), thendried over sodium sulfate, filtered and evaporated under reduced pressure to give 156.0 g of crude product. The obtained crude product was purified by column chromatography using silica gel (100-200 mesh) eluting with 4-7% EtOAc in hexane to afford Compound (42) as pale-brown solid (>96% pure by HPLC 260 nm, Mass (m / z): 345.20 [M+H]+).

[0338] 1H NMR (400 MHz, DMSO-t / 6): 5 7.47 (s, 1H), 7.10-7.06 (m, 2H), 6.79-6.75 (m,4H), 6.70 (dd, J= 8.4, 2.4 Hz, 1H), 6.61-6.57 (m, 1H), 5.44 (s, 1H), 2.26-2.21 (m, 2H), 2.09-2.04 (m, 2H), 1.68-1.55 (m, 8H), 1.47-1.41 (m, 4H), 1.15-1.09 (m, 1H)

[0339] 13C NMR (100 MHz, DMSO-t / 6): 5 147.19, 138.92, 136.36, 132.40, 129.39,124.50, 124.19, 122.57, 120.34, 117.35, 115.79, 114.35, 114.09, 54.80, 32.76, 25.56, 25.38, 25.00, 23.19, 22.59, 20.58EXAMPLE 12Synthesis of Compound (43)Compound (43)

[0340] A solution of 4-amino-diphenylamine (100.0 g, 0.543 mol) in DMF (1.0 L) was added cyclopentanone (240.6 mL, 5.0 eq) followed by p-TSA monohydrate (20.6 g, 0.108 mol), under nitrogen atmosphere at RT. The resulting reaction contents were heated to 115-120 °C and stirred for 16 h. After completion of reaction, (monitored by TLC), cooled to RT, quenched with ice cold water (500 mL) and extracted with ethyl acetate (1.0 L). The organic layer was separated, dried over sodium sulfate, filtered and evaporated under reduced pressure to give 138.0 g of crude product. The obtained crude product was purified by column chromatography using silica gel (100-200 mesh) eluting with 4-7% EtOAc in hexane to afford 38 g of Compound (43) as pale-yellow solid (>96% pure by HPLC 260 nm, Mass (m / z): 317.6 [M+H]+).

[0341] 1H NMR (400 MHz, DMSO-t / 6): 5 7.43 (s, 1H), 7.07 (d, J= 7.6 Hz, 2H), 6.75 (d,J= 8.0 Hz, 2H), 6.66 (dd, J= 8.4, 2.0 Hz, 1H), 6.56 (t, J= 7.6 Hz, 1H), 5.54 (d, J= 2.4 Hz, 1H), 6.48 (d, J= 8.4, 1H), 5.64 (s, 1H), 2.47-2.44 (m, 4H), 1.95-1.88 (m, 2H), 1.82-1.73 (m, 4H), 1.63-1.54 (m, 4H)

[0342] 13CNMR (100 MHz, DMSO-t / 6): 5 147.34, 139.66, 139.52, 131.44, 131.29,129.40, 121.74, 120.12, 117.25, 113.96, 112.63, 64.61, 32.21, 31.07, 24.21, 22.26EXAMPLE 13Oxidative Induction Time (OIT) Performance of Compounds of the Disclosure

[0343] 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.

[0344] 0.5 wt % of a Compound of the Disclosure, A1-(4-methylpentan-2-yl)-A4- phenylbenzene-l,4-diamine (6PPD), or no antidegradant (blank) was mixed with polyisoprene 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 4EXAMPLE 14Use of Compounds of the Disclosure in Sidewall Formulations

[0345] Rubber sidewall compounds were prepared using Compounds of the Disclosure as anti degradants in sidewall formulations. As shown in Table 5, the rubber sidewall compounds are a 50 / 50 blend of natural rubber and butadiene rubber with a carbon black of the N500 series. Example #1 is a sidewall compound comprising Compound 1,Example #B1 is a sidewall compound comprising Compound Bl, and Example #6 is a is a sidewall compound comprising Compound 6. A control sidewall compound comprising no antidegradant was also prepared. According to American Society for Testing Materials (ASTM) test method D5289, vulcanization properties of all the compounds were characterized by a moving die rheometer (Alpha Technologies MDR 2000), also known as MDR, at a temperature of 160 °C for 60 minutes. The oscillation strain and frequency were set to 0.5 °C and 1.667 Hz, respectively. The MDR test results are summarized in Table 6.Table 5Table 61ML is the minimum torque, which is a measure of rigidity and viscosity of the nonvulcanized compound.2MH is the maximum torque, which is a measure of the cross-linking density of the fully vulcanized compound.3tMH is the time taken to reach maximum torque.4ts 1 is the time for viscosity to increase 1 unit (dNm) above ML.5ts2 is the time for viscosity to increase 2 units (dNm) above ML.6tl 0 is the moment when 10% cross-linking has been reached.7t25 is the moment when 25% cross-linking has been reached.8t50 is the moment when 50% cross-linking has been reached.9t90 is the moment when 90% cross-linking has been reached.EXAMPLE 15Antiozonant Performance of Compounds of the Disclosure in Sidewall Compounds

[0346] The rubber sidewall compounds prepared in Example 14 were cured at 160 °C to a state equivalent to its T90+2 min time. The ozone test specimens were died out from vulcanized tensile sheets by using a die followed the American Society for Testing and Materials (ASTM) DI 329 standard. The ozone test specimens were stored in an ambient environment for more than 24 hours prior to antiozonant performance testing in an ozone chamber, which was maintained at an ozone concentration of 10 ± 2 parts per hundred million (pphm) and 40 ± 2 °C. The ozone test specimens were simultaneously relaxed and extended within ozone chamber under dynamic conditions. The ozone test specimens were alternately relaxed and extended to 25% strain at a rate of 90 cycles per minute during dynamic exposure. Exposure was in increments of 16 hours or 24 hours followed by at least one hour of relaxation after removal from the ozone chamber and prior to measurement of force at a strain of 100%.

[0347] Antiozonant performance of antidegradant formulated compounds were evaluated by percentage of force retention. The percentage of force retention is defined by equation 1.Equation 1 : Percentage of force retention = F / Fo * 100%wherein Fo is the force at a strain of 100% prior to ozone testing and F is the force at a strain of 100% after samples are aged in ozone chamber for 16-hour cycle at dynamic exposure. Higher percentage of force retention is an indication of better antiozonant performance of an antidegradant compound incorporated in the vulcanized rubber compound.

[0348] The force of aged and unaged ozone test specimens was measured by using a tensometer (Alpha Technologies, 2000) at a strain of 100%. The percentage of force retention for the sidewall compounds were calculated and plotted as a function of ozone aging time in Fig. 13 (Example #1), Fig. 14 (Example #B1), and Fig. 16 (Example #6).EXAMPLE 16Use of Compounds of the Disclosure in Tread Formulations

[0349] Rubber tread compounds were prepared using Compounds of the Disclosure as an antidegradant in tread formulations. As shown in Table 7, these rubber tread compounds are a 70 / 30 blend of styrene-butadiene rubber and butadiene rubber with silica and carbon black. Example #la is a tread compound comprising Compound 1 and Example #6a is a tread compound comprising Compound 6. A control tread compound comprising no antidegradant was also prepared. According to American Society for Testing Materials (ASTM) test method D5289, vulcanization properties of all the compounds were characterized by a moving die rheometer (Alpha Technologies MDR 2000), also known as MDR, at a temperature of 160 °C for 60 minutes. The oscillation strain and frequency were set to 0.5 °C and 1.667 Hz, respectively. The MDR test results were summarized in Table 8.Table 7Table 8'ML is the minimum torque, which is a measure of rigidity and viscosity of the nonvulcanized compound.2MH is the maximum torque, which is a measure of the cross-linking density of the fully vulcanized compound.3tMH is the time taken to reach maximum torque.4ts 1 is the time for viscosity to increase 1 unit (dNm) above ML.5ts2 is the time for viscosity to increase 2 units (dNm) above ML.6tl 0 is the moment when 10% cross-linking has been reached.7t25 is the moment when 25% cross-linking has been reached.8t50 is the moment when 50% cross-linking has been reached.9t90 is the moment when 90% cross-linking has been reached.EXAMPLE 17Antiozonant Performance of Compounds of the Disclosure in Tread Compounds

[0350] Each of the rubber tread compounds prepared in Example 16 were cured at 160 °C to a state equivalent to its T90+2 min time. The ozone test specimens were died out from vulcanized tensile sheets by using a die followed the American Society for Testing and Materials. (ASTM) DI 329 standard. The ozone test specimens were stored in an ambient environment for more than 24 hours prior to antiozonant performance testing in an ozone chamber, which was maintained at an ozone concentration of 10 ± 2 parts per hundred million (pphm) and 40 ± 2 °C. The ozone test specimens were simultaneously relaxed and extended within ozone chamber under dynamic conditions. The ozone test specimens extended to 25% strain at a rate of 90 cycles per minute during dynamic exposure. Exposure was in increments of 16 hours followed by at least one hour of relaxation after removal from the ozone chamber and prior to measurement of force at a strain of 100%.

[0351] Antiozonant performance of antidegradant formulated compounds were evaluated by percentage of force retention, which is defined in Example 15 and Fig. 17.

[0352] The percentage of force retention for the tread compounds were calculated and plotted as a function of ozone aging time in Fig. 15.

[0353] Having now fully described the methods, compounds, and compositions herein, it will be understood by those of skill in the art that the same can be performed within a wide and equivalent range of conditions, formulations, and other parameters without affecting the scope of the methods, compounds, and compositions provided herein or any embodiment thereof. All patents, patent applications, and publications cited herein are fully incorporated by reference herein in their entirety.

Claims

What is claimed is:

1. A compound having Formula (I):or a salt, solvate, or stereoisomer thereof, wherein:= is a single or a double bond;R1is selected from the group consisting of optionally substituted C1-C12 alkyl, optionally substituted C2-C6 alkenyl, -CHRlaRlb, C3-C7 cycloalkyl, 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, -C(=O)R4, -C(=O)OR4, and -SO2R4;Rlais 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;Rlbis selected from the group consisting of hydrogen and C1-C9 alkyl;Rlcis selected from the group consisting of hydrogen and Ci-Ce alkyl;R2a, R2Iand R2care hydrogen;R3ais selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, optionally substituted phenyl, -C(=O)OR4, -C(=O)NR4R5, -C(=O)SR4, -CH2OR4, -CH2OC(=O)R4, andR3bis selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl; orR3aand R3btaken together with the carbon atom to which they are attached form a C3-C12 cycloalkyl;R3Cis selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, optionally substituted phenyl, -C(=O)OR4, -C(=O)NR4R5, -C(=O)SR4, -CH2OR4, -CH2OC(=O)R4, andR3dis selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl; orR3Cand R3dtaken together with the two carbon atoms to which they are attached form aC3-C12 cycloalkyl;R3eis selected from the group consisting of hydrogen, Ci-Ce alkyl, optionally substitutedC2-C6 alkenyl, -C(=O)R4, -C(=O)OR4, and -SO2R4;Z at each occurrence is independently selected from the group consisting of -O-, -S-, and-NR7-;R4at each occurrence is independently selected from the group consisting of hydrogen,C1-C9 alkyl, C1-C9 haloalkyl, C3-C7 cycloalkyl, and optionally substituted phenyl; andR5at each occurrence is independently selected from the group consisting of hydrogen,C1-C9 alkyl, C3-C7 cycloalkyl, and optionally substituted phenyl;R6a, R6b, R6C, and R6dat each occurrence are independently selected from the group consisting of hydrogen, C1-C12 alkyl, and optionally substituted phenyl; andR7at each occurrence is independently selected from the group consisting or hydrogen and Ci-Ce alkyl, with the proviso that the compound of Formula (I) is not:

2. The compound of claim 1, or a salt, solvate, or stereoisomer thereof, havingFormula (Ila):(Ila).

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

4. The compound of any one of claims 1-3, or a salt, solvate, or stereoisomer thereof, wherein R3a, R3b, and R3care independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, or nonyl.

5. The compound of claim 4, or a salt, solvate, or stereoisomer thereof, wherein R3a, R3b, and R3care methyl, ethyl, or iso-butyl.

6. The compound of claim 5, or a salt, solvate, or stereoisomer thereof, wherein R3aand R3care methyl.

7. The compound of claim 5, or a salt, solvate, or stereoisomer thereof, wherein R3aand R3care ethyl.

8. The compound of claim 5, or a salt, solvate, or stereoisomer thereof, wherein R3aand R3care iso-butyl.

9. The compound of any one of claims 5-8, or a salt, solvate, or stereoisomer thereof, wherein R3bis methyl.

10. The compound of claim 4, or a salt, solvate, or stereoisomer thereof, wherein R3aand R3bare methyl.

11. The compound of claim 4, or a salt, solvate, or stereoisomer thereof, wherein R3aand R3bare ethyl.

12. The compound of claim 4, or a salt, solvate, or stereoisomer thereof, wherein R3ais ethyl and R3bis methyl.

13. The compound of any one of claims 10-12, or a salt, solvate, or stereoisomer thereof, wherein R3cis hydrogen.

14. The compound of any one of claims 1-3, or a salt, solvate, or stereoisomer thereof, wherein R3aand R3care -C(=O)OR4, -C(=O)NR4R5, -C(=O)SR4, -CH2OR4, -CH2OC(=O)R4, or15. The compound of claim 14, or a salt, solvate, or stereoisomer thereof, wherein R3aand R3Care -C(=O)OR4.

16. The compound of claim 15, or a salt, solvate, or stereoisomer thereof, wherein each R4is hydrogen, methyl or ethyl.

17. The compound of claim 16, or a salt, solvate, or stereoisomer thereof, wherein each R4is ethyl.

18. The compound of any one of claims 14-17, or a salt, solvate, or stereoisomer thereof, wherein R3bis methyl.

19. The compound of any one of claims 1-18, or a salt, solvate, or stereoisomer thereof, wherein R3dis hydrogen.

20. The compound of any one of claims 1-19, or a salt, solvate, or stereoisomer thereof, wherein R1is optionally substituted phenyl.

21. The compound of any one of claims 1-19, or a salt, solvate, or stereoisomer thereof, wherein R1is C1-C12 alkyl.

22. The compound of claim 21, or a salt, solvate, or stereoisomer thereof, wherein R1is methyl, ethyl, propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, or nonyl.

23. The compound of claim 22, or a salt, solvate, or stereoisomer thereof, wherein R124. The compound of any one of claims 1-19, or a salt, solvate, or stereoisomer thereof, wherein R1is -CHRlaRlb.

25. The compound of claim 24, or a salt, solvate, or stereoisomer thereof, wherein Rlais phenyl, 2-furyl, or 2-tetrahydrofuryl.

26. The compound of claim 24 or 25, or a salt, solvate, or stereoisomer thereof, wherein Rlbis hydrogen or methyl.

27. The compound of any one of claims 1-26, or a salt, solvate, or stereoisomer thereof, wherein Rlcis Ci-Ce alkyl.

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

29. The compound of any one of claims 1-26, or a salt, solvate, or stereoisomer thereof, wherein Rlcis hydrogen.

30. The compound of any one of claims 1-29, or a salt, solvate, or stereoisomer thereof, wherein R3eis Ci-Ce alkyl.

31. The compound of claim 30, or a salt, solvate, or stereoisomer thereof, wherein R3eis methyl.

32. The compound of any one of claims 1-29, or a salt, solvate, or stereoisomer thereof, wherein R3eis hydrogen.

33. The compound of any one of claims 1-29, or a salt, solvate, or stereoisomer thereof, wherein R3eis -C(=O)R4.

34. The compound of claim 33, or a salt, solvate, or stereoisomer thereof, wherein R4is methyl.

35. The compound of any one of claims 1-29, or a salt, solvate, or stereoisomer thereof, wherein R3eis -SO2R4.

36. The compound of claim 35, or a salt, solvate, or stereoisomer thereof, wherein R4is C6H5CH3.

37. The compound of any one of claims 1-3, or a salt, solvate, or stereoisomer thereof, wherein R3aand R3btaken together with the carbon atom to which they are attached form a C3- C12 cycloalkyl.

38. The compound of claim 37, or a salt, solvate, or stereoisomer thereof, wherein R3aand R3btaken together with the carbon atom to which they are attached form a cyclobutyl, cyclopentyl, or cyclohexyl.

39. The compound of any one of claims 1-3 or 36-38, or a salt, solvate, or stereoisomer thereof, wherein R3cand R3dtaken together with the two carbon atoms to which they are attached form a C3-C12 cycloalkyl.

40. The compound of claim 39, or a salt, solvate, or stereoisomer thereof, wherein R3cand R3dtaken together with the two carbon atoms to which they are attached form a cyclopentyl, a cyclopentenyl, a cyclohexyl, or a cyclohexenyl.

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

42. A compound having Formula (IV):or a salt, solvate, or stereoisomer thereof, wherein: each = is independently a single or a double bond;R8aand R8bare independently selected from the group consisting of hydrogen, halogen, Ci- C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, Ci-Cs alkoxy, Ci-Cs alkylthio, C(=O)OR4, -OC(=O)R4, -C(=O)NR4R5, -NR4C(=O)R5, -NR4R5, -OH, -SH, -SC(=O)R4, -SC(=O) SR4, -SC(=O)NR4R5, -NR4C(=O)SR5, -NR4C(=S)SR5, 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio, and arylamino;R9ais selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, optionally substituted phenyl, -C(=O)OR4, -C(=O)NR4R5, -C(=O)SR4, -CH2OR4, -CH2OC(=O)R4, andR9bis selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl; orR9aand R9btaken together with the carbon atom to which they are attached form a C3-C12 cycloalkyl;R9Cis selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, optionally substituted phenyl, -C(=O)OR4, -C(=O)NR4R5, -C(=O)SR4, -CH2OR4, -CH2OC(=O)R4, andR9dis selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl; orR9Cand R9dtaken together with the two carbon atoms to which they are attached form aC3-C12 cycloalkyl;R9eis selected from the group consisting of hydrogen, Ci-Ce alkyl, optionally substitutedC2-C6 alkenyl, -C(=O)R4, -C(=O)OR4, and -SO2R4;R10ais selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, optionally substituted phenyl, -C(=O)OR4, -C(=O)NR4R5, -C(=O)SR4, -CH2OR4, -CH2OC(=O)R4, andR10bis selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl; orR10aand R10btaken together with the carbon atom to which they are attached form a C3- C12 cycloalkyl;R10cis selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, optionally substituted phenyl, -C(=O)OR4, -C(=O)NR4R5, -C(=O)SR4, -CH2OR4, -CH2OC(=O)R4, andR10dis selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl; orR10cand R10dtaken together with the two carbon atoms to which they are attached form a C3-C12 cycloalkyl;R10eis selected from the group consisting of hydrogen, Ci-Ce alkyl, optionally substituted C2-C6 alkenyl, -C(=O)R4, -C(=O)OR4, and -SO2R4;Z at each occurrence is independently selected from the group consisting of -O-, -S-, and -NR7-;R4at each occurrence is independently selected from the group consisting of hydrogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C7 cycloalkyl, and optionally substituted phenyl; andR5at each occurrence is independently selected from the group consisting of hydrogen, C1-C9 alkyl, C3-C7 cycloalkyl, and optionally substituted phenyl;R6a, R6b, R6C, and R6dat each occurrence are independently selected from the group consisting of hydrogen, C1-C12 alkyl, and optionally substituted phenyl; andR7at each occurrence is independently selected from the group consisting or hydrogen and Ci-Ce alkyl.

43. The compound of claim 42, or a salt, solvate, or stereoisomer thereof, having Formula (V):

44. The compound of claim 42, or a salt, solvate, or stereoisomer thereof, having Formula (VI):

45. The compound of any one of claims 42-44, or a salt, solvate, or stereoisomer thereof, wherein R8aand R8bare hydrogen or methyl.

46. The compound of any one of claims 42-45, or a salt, solvate, or stereoisomer thereof, wherein R9a, R9b, and R9care independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, and nonyl.

47. The compound of claim 46, or a salt, solvate, or stereoisomer thereof, wherein R9a, R9b, and R9care methyl, ethyl, or iso-butyl.

48. The compound of claim 47, or a salt, solvate, or stereoisomer thereof, wherein R9aand R9Care methyl.

49. The compound of claim 47, or a salt, solvate, or stereoisomer thereof, wherein R9aand R9Care ethyl.

50. The compound of claim 47, or a salt, solvate, or stereoisomer thereof, wherein R9aand R9Care iso-butyl.

51. The compound of claim 46, or a salt, solvate, or stereoisomer thereof, wherein R9aand R9bare methyl.

52. The compound of claim 46, or a salt, solvate, or stereoisomer thereof, wherein R9aand R9bare ethyl.

53. The compound of claim 46, or a salt, solvate, or stereoisomer thereof, wherein R9ais ethyl and R9bis methyl.

54. The compound of any one of claims 51-53, or a salt, solvate, or stereoisomer thereof, wherein R9cis hydrogen.

55. The compound of any one of claims 42-45, or a salt, solvate, or stereoisomer thereof, wherein R9aand R9care -C(=O)OR4, -C(=O)NR4R5, -C(=O)SR4, -CH2OR4, -CH2OC(=O)R4, or56. The compound of claim 55, or a salt, solvate, or stereoisomer thereof, wherein R9aand R9Care -C(=O)OR4.

57. The compound of claim 56, or a salt, solvate, or stereoisomer thereof, wherein each R4is hydrogen, methyl or ethyl.

58. The compound of claim 57, or a salt, solvate, or stereoisomer thereof, wherein each R4is ethyl.

59. The compound of any one of claims 55-58, or a salt, solvate, or stereoisomer thereof, wherein R9bis methyl.

60. The compound of any one of claims 42-59, or a salt, solvate, or stereoisomer thereof, wherein R9dis hydrogen.

61. The compound of any one of claims 42-60, or a salt, solvate, or stereoisomer thereof, wherein R10a, R10b, and R10care independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, and nonyl.

62. The compound of claim 61, or a salt, solvate, or stereoisomer thereof, wherein Ri°a, R10b, and R10care methyl, ethyl, or iso-butyl.

63. The compound of claim 62, or a salt, solvate, or stereoisomer thereof, wherein R10aand R10care methyl.

64. The compound of claim 63, or a salt, solvate, or stereoisomer thereof, wherein R10aand R10care ethyl.

65. The compound of claim 63, or a salt, solvate, or stereoisomer thereof, wherein R10aand R10care iso-butyl.

66. The compound of claim 61, or a salt, solvate, or stereoisomer thereof, wherein R10aand R10bare methyl.

67. The compound of claim 61, or a salt, solvate, or stereoisomer thereof, wherein R10aand R10bare ethyl.

68. The compound of claim 61, or a salt, solvate, or stereoisomer thereof, wherein R10ais ethyl and R10bis methyl.

69. The compound of any one of claims 66-68, or a salt, solvate, or stereoisomer thereof, wherein R10cis hydrogen.

70. The compound of any one of claims 42-60, or a salt, solvate, or stereoisomer thereof, wherein R10aand R10care -C(=O)OR4, -C(=O)NR4R5, -C(=O)SR4, -CH2OR4, -CH2OC(=O)R4, or71. The compound of claim 70, or a salt, solvate, or stereoisomer thereof, wherein R10aand R10care -C(=O)OR472. The compound of claim 71, or a salt, solvate, or stereoisomer thereof, wherein each R4is hydrogen, methyl or ethyl.

73. The compound of claim 72, or a salt, solvate, or stereoisomer thereof, wherein each R4is ethyl.

74. The compound of any one of claims 58-73, or a salt, solvate, or stereoisomer thereof, wherein R10bis methyl.

75. The compound of any one of claims 42-74, or a salt, solvate, or stereoisomer thereof, wherein R10dis hydrogen.

76. The compound of any one of claims 42-75, or a salt, solvate, or stereoisomer thereof, wherein R9aand R10aare the same.

77. The compound of any one of claims 42-76, or a salt, solvate, or stereoisomer thereof, wherein R9band R10bare the same.

78. The compound of any one of claims 42-77, or a salt, solvate, or stereoisomer thereof, wherein R9cand R10care the same.

79. The compound of any one of claims 42-78, or a salt, solvate, or stereoisomer thereof, wherein R9dand R10dare the same.

80. The compound of any one of claims 42-79, or a salt, solvate, or stereoisomer thereof, wherein R9eis Ci-Ce alkyl.

81. The compound of claim 80, or a salt, solvate, or stereoisomer thereof, wherein R9eis methyl.

82. The compound of any one of claims 42-79, or a salt, solvate, or stereoisomer thereof, wherein R9eis hydrogen.

83. The compound of any one of claims 42-82, or a salt, solvate, or stereoisomer thereof, wherein R10eis Ci-Ce alkyl.

84. The compound of claim 83, or a salt, solvate, or stereoisomer thereof, wherein R10eis methyl.

85. The compound of any one of claims 42-82, or a salt, solvate, or stereoisomer thereof, wherein R10eis hydrogen.

86. The compound of claim 42, or a salt, solvate, or stereoisomer thereof, selected from any one or more of the compounds of Table 2.

87. A composition comprising:(i) the compound of any one of claims 1-86; 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.

88. The composition of claim 87, wherein the composition comprises one or more elastomers.

89. The composition of claim 88, wherein the composition comprises from about0.1 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.

90. The composition of any one of claims 87-89, wherein the one or more elastomers comprise natural rubber (NR).

91. The composition of claim 90, wherein the one or more elastomers comprises from about 5 wt / wt % to about 100 wt / wt % natural rubber (NR).

92. The composition of claim 90 or 91, wherein the natural rubber comprises rubber derived from an alternative rubber plant.

93. The composition of claim 92, wherein the alternative rubber plant is Parthenium argentatum (guayule) or Taraxacum kok-saghyz (Russian dandelion).

94. The composition of any one of claims 88-93, wherein the one or more elastomers comprise synthetic rubber.

95. The composition of claim 94, 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.

96. The composition of claim 95, 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.

97. The composition of claim 96, wherein the unsaturated rubber comprises styrene butadiene rubber (SBR).

98. The composition of claim 97, wherein the one or more elastomers comprise from about 5 wt / wt % to about 100 wt / wt % styrene butadiene rubber (SBR).

99. The composition of any one of claims 96-98, wherein the unsaturated rubber comprises polybutadiene rubber (BR).

100. The composition of claim 99, wherein the one or more elastomers comprise from about 5 wt / wt % to about 80 wt / wt % polybutadiene rubber (BR).

101. The composition of any one of claims 96-100, wherein the unsaturated rubber comprises butyl rubber (IIR).

102. The composition of claim 101, wherein the one or more elastomers comprise from about 1 wt / wt % to about 30 wt / wt % butyl rubber (IIR).

103. The composition of any one of claims 95-102, 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.

104. The composition of claims any one of claims 87-103, wherein the one or more elastomers further comprises recycled rubber.

105. The composition of any one of claims 87-104, wherein the composition comprises from about 0.1 phr to about 10 phr of the compound.

106. The composition of claim 105, wherein the composition comprises from about 0.5 phr to about 5 phr of the compound.

107. The compound of claim 106, wherein the composition comprises from about 1 phr to about 5 phr of the compound.

108. The composition of any one of claims 87-107, wherein the composition comprises one or more fillers.

109. The composition of claim 108, wherein the composition comprises from about 15 wt / wt % to about 85 wt / wt % of the compound and from about 15 wt / wt % to about 85 wt / wt % of the one or more fillers.

110. The composition of claims 108 or 109, wherein the composition comprises from about 30 phr to about 500 phr of one or more fillers.

111. The composition of any one of claims 108-110, 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.

112. The composition of claim 111, wherein the one or more fillers comprise silica.

113. The composition of claim 112, wherein the silica is derived from rice husks.

114. The composition of any one of claims 108-113, wherein the one or more fillers comprise carbon black.

115. The composition of any one of claims claim 87-114, wherein the composition comprises one or more rubber chemicals.

116. The composition of claim 115, wherein the composition comprises from about 15 wt / wt % to about 85 wt / wt % of the compound and from about 15 wt / wt % to about 85 wt / wt % of one or more rubber chemicals.

117. The composition of claims 115 or 116, wherein the composition comprises from about 0.1 phr to about 30 phr of one or more rubber chemicals.

118. The composition of claim 117, wherein the composition comprises from about 1 phr to about 20 phr of one or more rubber chemicals.

119. The composition of any one of claims 115-118, 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.

120. The composition of claim 119, wherein the one or more rubber chemicals comprise one or more vulcanizing agents.

121. The composition of claim 120, wherein the one or more vulcanizing agents comprise sulfur, peroxide, resin, or a combination thereof.

122. The composition of claim 121, wherein the sulfur is octasulfur (Ss), cyclododecasulfur (S12), polymeric sulfur, or a combination thereof.

123. The composition of claim 121, wherein the peroxide is benzoyl peroxide, dicumyl peroxide (DC), 2,5-dimethyl-2,5-di-(tert-butylperoxy)-3-hexyne (2,5 Tri), 2,5-dimethyl-2,5- di(tert-butylperoxy)hexane (DDPH), di-(2-tert-butylperoxyisopropyl)benzene (VC), butyl-4,4-di- (tert-butylperoxy)valerate (VAL), l,l-di(tert-butylperoxy)-3,3,5-trimethylcyclohexane (TMC), or a combination thereof.

124. The composition of claim 121, wherein the resin is a bonding resin.

125. The composition of claims 119-124, wherein the one or more rubber chemicals comprise one or more accelerators.

126. The composition of claim 125, 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.

127. The composition of claim 126, wherein the guanidine is diphenylguanidine (DPG).

128. The composition of claim 126, wherein the thiazole comprises 2-mercaptobenzothiazole (MBT), zinc 2-mercaptobenzothiazole (ZMBT), mercaptobenzothiazole disulfide (MBTS), / ' / - / ert-butyl-2 -benzothiazole sulfenimide (TBSI), or a combination thereof.

129. The composition of claim 126, wherein the sulfenamide comprises A- / c / 7-butyl-2- benzothiazylsulfenamide (TBBS), 7V-cyclohexylbenzothiazol-2-sulfenamide (CBS), dicyclohexyl-2-benzothiazolesulfenamide (DCBS), N-oxy di ethylene benzothiazole sulfenamide (OBTS), A-oxy di ethylenethiocarbamyl- / ' / '-oxy di ethylene sulfenamide (OTOS), thiocarbamyl sulfenamide, or a combination thereof.

130. The composition of claim 126, 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.

131. The composition of claim 126, 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.

132. The composition of any one of claims 119-131, wherein the one or more rubber chemicals comprise one or more activators.

133. The composition of claim 132, wherein the one or more activators comprise a metal oxide, an acid, a metal complex, or a combination thereof.

134. The composition of claim 133, wherein the metal oxide comprises zinc oxide, magnesium oxide, lead oxide, or a combination thereof.

135. The composition of claim 133, wherein the acid comprises stearic acid, lauric acid, or a combination thereof.

136. The composition of claim 133, wherein the metal complex comprises zinc ethylhexanoate.

137. The composition of any one of claims 119-136, wherein the one or more rubber chemicals comprise one or more pre-vulcanization inhibitors.

138. The composition of claim 137, wherein the one or more pre-vulcanization inhibitors comprise 7V-(cyclohexylthio)phthalimide (CTP), benzoic anhydride, salicylic anhydride, phthalic anhydride, or a combination thereof.

139. The composition of any one of claims 87-138, wherein the composition comprises one or more plasticizers.

140. The composition of claim 139, wherein the composition comprises from about 15 wt / wt % to about 85 wt / wt % of the compound and from about 15 wt / wt % to about 85 wt / wt % of one or more plasticizers.

141. The composition of claims 139 or 140, wherein the composition comprises from about 0.1 phr to about 30 phr of one or more plasticizers.

142. The composition of claim 141, wherein the composition comprises from about 1 phr to about 20 phr of one or more plasticizers.

143. The composition of any one of claims 139-142, 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.

144. The composition of claim 143, wherein the mineral oil is naphthenic oil, paraffinic oil, or aromatic oil.

145. The composition of claim 143, wherein the naturally derived oil is soybean oil, vegetable oil, or orange oil.

146. The composition of any one of claims 87-145, wherein the composition further comprises one or more additional anti degradants.

147. The composition of claim 146, wherein the composition comprises from about 15 wt / wt % to about 85 wt / wt % of the compound and from about 15 wt / wt % to about 85 wt / wt % of one or more additional anti degradants.

148. The composition of claim 146 or 147, wherein one or more additional anti degradants are present in an amount of from about 0.001 phr to about 10 phr.

149. The composition of claim 148, wherein one or more additional anti degradants are present in an amount of from about 0.1 phr to about 5 phr.

150. The composition of claim 149, wherein one or more additional anti degradants are present in an amount of from about 0.5 phr to about 5 phr.

151. The composition of claim 149, wherein one or more additional anti degradants are present in an amount of from about 1 phr to about 5 phr.

152. The composition of any one of claims 146-151, wherein one or more additional anti degradants are antioxidants.

153. The composition of any one of claims 146-151, wherein one or more additional anti degradants are antiozonants.

154. The composition of any one of claims 146-153, wherein one or more additional anti degradants are a paraphenylenediamine (PPD), a trimethyldihydroquinoline (TMQ), a phenolic, an alkylated diphenylamine (DPA), or a diphenylamine-ketone condensate.

155. The composition of claim 154, wherein the PPD is A1-(4-methylpentan-2-yl)-A4- phenylbenzene-l,4-diamine (6PPD), zV-(l ,4-di methyl pentyl )-A'-phenyl-p-phenylenediamine (7PPD), A1-phenyl-A4-(propan-2-yl)benzene-l,4-diamine (IPPD), 7V,A'-di - ec-butyl -p- phenylenediamine (44PD), A,A'-bis(l,3-dimethylbutyl)-p-phenylenediamine (66PD), N,N'~ bis(l,4-dimethylpentyl)-p-phenylenediamine (77PD), or A-A'-dioctyl- / ?-phenylenediamine (88PD).

156. The composition of claim 155, wherein the PPD is 6PPD.

157. The composition of claim 154, wherein the TMQ is 2,2,4-trimethyl-l,2- dihydroquinoline or an oligomer or polymer thereof.

158. A composition comprising the compound of any one of claims 1-86 and one or more carriers.

159. A process for preparing the composition of claim 158, the process comprising admixing the compound and the one or more carriers.

160. A vulcanized elastomeric article comprising the compound of any one of claims 1-86.

161. A vulcanized elastomeric article prepared using the composition of any one of claims 87-158.

162. The vulcanized elastomeric article of claims 160 or 161, wherein the vulcanized elastomeric article is a tire.

163. The vulcanized elastomeric article of claim 162, 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.

164. The vulcanized elastomeric article of claims 160 or 161, wherein the vulcanized elastomeric article is a component of a tire.

165. The vulcanized elastomeric article of claim 164, wherein the component is a bead, a belt, a body ply, an inner liner, a sidewall, an undertread, or a tread.

166. The vulcanized elastomeric article of claims 160 or 161, 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.

167. A process for preparing a vulcanized elastomeric article, the process comprising:(a) forming the composition of any one of claims 88-157 into a formed shape; and(b) vulcanizing the formed shape to provide a vulcanized elastomeric article.

168. The process of claim 167, wherein the vulcanizing is performed at an average temperature of from about 120 °C to about 180 °C.

169. The process of claim 168, wherein the vulcanizing is performed at an average temperature of from about 140 °C to about 160 °C.

170. The process of any one of claims 167-169, wherein the vulcanized elastomeric article is a tire.- I l l -171. The process of claim 170, 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.

172. The process of any one of claims 167-171, wherein the vulcanized elastomeric article is a component of a tire.

173. The process of claim 172, wherein the component is a bead, a belt, a body ply, an inner liner, a sidewall, an undertread, or a tread.

174. The process of any one of claims 167-169, 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.

175. A lubricant composition comprising a lubricant and the compound of any one of claims 1-86.

176. A combustible fuel composition comprising a combustible fuel and the compound of any one of claims 1-86.

177. A fuel additive composition comprising a fuel additive and the compound of any one of claims 1-86.

178. A process for retreading tires, the process comprising:(a) applying the composition of any one of claims 87-168 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.

179. A kit comprising the composition of any one of claims 87-168 and instructions for using the composition in a vulcanizable elastomeric composition.

180. A kit comprising the composition of any one of claims 87-168 and instructions for using the composition to prepare a vulcanized elastomeric article.

181. The composition of claim 87, wherein the composition comprises from about 0.1 wt / wt% to about 10 wt / wt% of the compound.

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