6-aminoquinoline antidegradants

Abstract

The present disclosure provides compounds represented by Formula (I): or salts, solvates, or stereoisomers thereof, wherein R1a, R1b, R2a, R2b, R2c, R3a, R3b, R3c, R3d, R3e, R3f, and R3g 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

6-AMINOQUINOLINE ANTIDEGRADANTSBACKGROUNDField

[0001] The present disclosure provides compounds with antidegradant, e.g., antiozonant, antioxidant and / or antifatigue, properties that are useful additives for vulcanized rubber articles, compositions comprising elastomers, lubricants, fuels, and other compositions which require such properties or in compositions which are themselves useful as compositions to impart such properties.Background

[0002] Many materials such as plastics, elastomers, elastomeric products (tires, belts, hoses, bushings, mounts, vibration isolators, etc.), lubricants and petroleum products (such as hydraulic fluids, oils, fuels and oil / fuel additives for automotive and aviation applications) are prone to degradation upon prolonged exposure to light, heat, oxygen, ozone, repetitive mechanical actions and the like. Accordingly, compounds and compositions demonstrating antidegradant efficacy are well known in the art. For example, U.S Patent No. 8,987,515 discloses an aromatic polyamine useful in inhibiting oxidative degradation particularly in lubricant compositions. U.S. Patent Application Publication No. 2014 / 0316163 discloses antioxidant macromolecules with purported improved solubility in many commercially available oils and lubricants.

[0003] Anti degradants useful in the manufacture of articles formed from elastomers, plastics and the like require a very specific combination of qualities that can be difficult to achieve. While the anti degradants must obviously have commercially acceptable efficacy, they must also exhibit that efficacy over prolonged periods of time associated with use of the article, particularly at exposed surfaces of the article where degradation from environmental factors such as light, oxygen and ozone primarily occurs. Just as important to the protection of surface exposed components, efficacy in protecting imbedded components of composite materials from the effects of oxidative aging and repetitive mechanical action are critically important. The anti degradants must achieve these results while not negatively impacting other additives' efficacy or desirable characteristics in the final article. Further, anti degradants which provide or improve themechanical fatigue life after an article has been in service, aged oxidatively or by exposure to ozone are highly valued since these will inherently improve the useful mechanical service life of article. Consequently, elastomeric articles which undergo repeated mechanical flexure, extension, or compression during service would greatly benefit from such a discovery.

[0004] Articles formed from general purpose elastomers such as natural rubber, in particular tires, are especially prone to degradation from both oxygen and ozone. As discussed in U.S. Patent No. 2,905,654, the effect on rubber from degradation by oxygen is different from the effect from degradation from ozone; however, both effects can be detrimental to tire performance, appearance and life expectancy. Fatigue and crack propagation are also issues of specific concern, in particular for steel belt edge areas and tire sidewalls which are subject to significant stresses and stretching forces while flexed whether inflated, partially inflated, uninflated and throughout the service life of the tire. U.S. Patent No. 8,833,417 describes an antioxidant system that purportedly increases long-term resistance to fatigue and crack propagation over the known antioxidants discussed immediately below.

[0005] Materials with antidegradant efficacy are well known in the art for use in tire applications and are commercially available. For example, A,A-disubstituted- paraphenylenediamines such as those sold under the trademark Santoflex® are generally favored by many tire manufacturers for this purpose. EP 3147321 Al discloses rubber compositions, tires, amine compounds, and anti -aging agents, and in particular, a rubber composition that is said to be suitable for use in tread rubber or sidewall rubber of a tire.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)-(III), below, collectively referred to herein as "Compounds of the Disclosure" or individually as a "Compound of the Disclosure."

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

[0026] Fig. l is a line graph depicting aJH nuclear magnetic resonance (NMR) spectrum of intermediate compound 1-1 in tAdimethyl sulfoxide (t / e-DMSO).

[0027] Fig. 2 is a line graph depicting a13C APT NMR spectrum of intermediate compound 1-1 in t / e-DMSO.

[0028] Fig. 3 is a liquid chromatography (LC) chromatogram of intermediate compound1-1.

[0029] Fig. 4 is a line graph depicting a13C APT NMR spectrum of Compound 1 in ^ / -chloroform (CDCh).

[0030] Fig. 5 is an LC chromatogram of Compound 1.

[0031] Fig. 6 is a line graph depicting a13C APT NMR spectrum of Compound 2 in MSO.

[0032] Fig. 7 is an LC chromatogram of Compound 2.

[0033] Fig. 8 is an LC chromatogram of intermediate compound 3-1.

[0034] Fig. 9 is a line graph depicting a13C APT NMR spectrum of Compound 3 in MSO.

[0035] Fig. 10 is an LC chromatogram of Compound 3.

[0036] Fig. 11 is a line graph depicting a13C APT NMR spectrum of intermediate compound 4-1 in tL-DMSO.

[0037] Fig. 12 is an LC chromatogram of intermediate compound 4-1.

[0038] Fig. 13 is a line graph depicting a13C APT NMR spectrum of Compound 4 in MSO.

[0039] Fig. 14 is an LC chromatogram of Compound 4.

[0040] Fig. 15 is a line graph depicting a13C APT NMR spectrum of intermediate compound 47-1 in tL-DMSO.

[0041] Fig. 16 is an LC chromatogram of intermediate compound 47-1.

[0042] Fig. 17 is a line graph depicting a13C APT NMR spectrum of Compound 47 in MSO.

[0043] Fig. 18 is an LC chromatogram of Compound 47.DETAILED DESCRIPTION

[0044] In one embodiment, Compounds of the Disclosure are compounds having Formula (I):or a salt, solvate, or stereoisomer thereof, wherein:

[0045] = is a single or a double bond;

[0046] Rlais selected from the group consisting of optionally substituted C1-C12 alkyl, -CHRlcRld, C3-C6 cycloalkyl, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;

[0047] Rlbis selected from the group consisting of hydrogen and C1-C9 alkyl;

[0048] Rlcis selected from the group consisting of optionally substituted phenyl, C3-C6 cycloalkyl, and optionally substituted 5- or 6-membered heteroaryl;

[0049] Rldis selected from the group consisting of hydrogen and C1-C9 alkyl;

[0050] 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, -NHR4, -NR4R5, -OH, -SH, -SC(= O)R4, -SC(=O)SR4, -SC(=O)NHR4, -SC(=O)NR4R5, -NHC(=O)SR4, -NR4C(=O)SR5, -N HC(=S)SR4, -NR4C(=S)SR5, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl; or

[0051] R2bis 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, -NHR4, -NR4R5, -OH, -SH, -SC(= O)R4, -SC(=O)SR4, -SC(=O)NHR4, -SC(=O)NR4R5, -NHC(=O)SR4, -NR4C(=O)SR5, -N HC(=S)SR4, -NR4C(=S)SR5, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl; and

[0052] R2aand R2ctogether with the two carbon atoms to which they are attached form a C5-C8 cycloalkyl, a 5- to 8-membered heterocyclyl, or a Cs-Ce aryl;

[0053] R3aand R3bare independently selected from the group consisting of hydrogen, Ci- C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl, with the proviso that if = is a double bond, R3bis absent; or

[0054] R3aand R3btogether with the carbon atom to which they are attached form a C3-C12 cycloalkyl, with the proviso that = is a single bond;

[0055] R3Cand R3dare independently selected from the group consisting of hydrogen, Ci- C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl, with the proviso that if = is a double bond, R3dis absent; or

[0056] R3Cand R3dtogether with the carbon atom to which they are attached form a C3-C12 cycloalkyl, with the proviso that = is a single bond;

[0057] R3eand R3fare independently selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, -OH, -SH, Ci-Cs alkoxy, Ci-Cs alkylthio, arylthio,C(=O)OR4, -OC(=O)R4, -C(=O)NR4R5, -NR4C(=O)R5, -NHR4, -NR4R5, -SC(=O)R4, -SC(=O)SR4, -SC(=O)NHR4, -SC(=O)NR4R5, -NHC(=O)SR4, -NR4C(=O)SR5, -NHC(=S)SR4, -NR4C(=S)SR5, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl; or

[0058] R3eand R3ftaken together with the carbon atom to which they are attached form a C3-C12 cycloalkyl;

[0059] R3gis selected from the group consisting of hydrogen and C1-C9 alkyl; and

[0060] R4and R5are at each occurrence independently selected from the group consisting of hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl.

[0061] In another embodiment, Compounds of the Disclosure are compounds havingFormula (I), with the proviso that if R3eand / or R3fare hydrogen, R3cand R3dare independently selected from the group consisting of C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl.

[0062] In another embodiment, Compounds of the Disclosure are compounds havingFormula (II):wherein Rla, R2a, R2b, R2c, R3a, R3b, R3c, R3d, R3e, and R3fare as defined in connection with Formula (I).

[0063] In some embodiments, Compounds of the Disclosure are compounds of Formula (II), wherein:

[0064] R3Cand R3dare independently selected from the group consisting of C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl; or

[0065] R3Cand R3dtogether with the carbon atom to which they are attached form a C3-C12 cycloalkyl.

[0066] In some embodiments, Compounds of the Disclosure are compounds of Formula (II), wherein:

[0067] R3eand R3fare independently selected from the group consisting of halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, -OH, -SH, Ci-Cs alkoxy, Ci-Cs alkylthio, arylthio,C(=O)OR4, -OC(=O)R4, -C(=O)NR4R5, -NR4C(=O)R5, -NHR4, -NR4R5, -SC(=O)R4, -SC(=O)SR4, -SC(=O)NHR4, -SC(=O)NR4R5, -NHC(=O)SR4, -NR4C(=O)SR5, -NHC(=S)SR4, -NR4C(=S)SR5, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl; or

[0068] R3eand R3ftaken together with the carbon atom to which they are attached form aC3-C12 cycloalkyl.

[0069] In some embodiments, Compounds of the Disclosure are compounds of Formula (I) or Formula (II), wherein R3bis hydrogen.

[0070] In some embodiments, Compounds of the Disclosure are compounds having Formula (III):wherein Rla, R2a, R2b, R2c, R3a, R3c, R3e, and R3fare as defined in connection with Formula (I).

[0071] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein Rlais optionally substituted phenyl.

[0072] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein Rlais C1-C12 alkyl.

[0073] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein Rlais methyl, ethyl, propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, or nonyl.

[0074] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein wherein Rlais iso-propyl or sec-butyl.

[0075] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein wherein Rlais:

[0076] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R2a, R2b, and R2care independently selected from the group consisting of hydrogen and C1-C9 alkyl.

[0077] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R2band R2care hydrogen.

[0078] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R2ais selected from the group consisting of hydrogen and C1-C4 alkyl.

[0079] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R3ais hydrogen.

[0080] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R3ais C1-C9 alkyl.

[0081] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R3ais C3-C6 cycloalkyl.

[0082] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R3ais optionally substituted phenyl.

[0083] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R3cis hydrogen.

[0084] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R3cis C1-C9 alkyl.

[0085] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R3cis C3-C6 cycloalkyl.

[0086] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R3cis optionally substituted phenyl.

[0087] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R3eis hydrogen.

[0088] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R3eis Ci-Cs alkoxy.

[0089] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R3eis -OH.

[0090] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R3eis -SH.

[0091] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R3eis Ci-Cs alkylthio.

[0092] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R3eis arylthio.

[0093] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R3eis C1-C9 alkyl.

[0094] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R3eis C3-C6 cycloalkyl.

[0095] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R3eis optionally substituted phenyl.

[0096] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R3fis hydrogen.

[0097] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R3fis C1-C9 alkyl.

[0098] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R3fis C3-C6 cycloalkyl.

[0099] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R3fis optionally substituted phenyl.

[0100] 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

[0101] 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.

[0102] Compounds of the Disclosure can be prepared, for example, by a two-step process comprising i) reacting a 4-nitroaniline with an alkene and an aldehyde or ketone in acetonitrile or other suitable solvents and a catalyst such as any suitable acid or I2, i.e., via a Povarov reaction, and ii) reacting the product of step i) with an aldehyde or ketone under reductive conditions, e.g., pressurized H2 with a platinum catalyst, as shown in Scheme 1, wherein Rleis, for example, C1-C12 alkyl, C3-C6 cycloalkyl, optionally substituted phenyl, or optionally substituted 5- or 6-membered heteroaryl, and Rlfis, for example, hydrogen or Ci-Ce alkyl.Scheme 1

[0103] Compounds of the Disclosure can also be prepared by oxidizing the compound obtained in Scheme 1 by methods known in the art, as shown in Scheme 2.Scheme 2Definitions

[0104] 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.

[0105] 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)ORh, wherein R11is Ci-Ce alkyl.

[0106] The term "aryl" as used herein by itself or as part of another group refers to an aromatic ring system having six to fourteen carbon atoms, i.e., C6-C14 aryl. Non-limiting exemplary aryl groups include phenyl (abbreviated as "Ph"), naphthyl, phenanthryl, anthracyl, indenyl, azulenyl, biphenyl, biphenylenyl, and fluorenyl groups. In one embodiment, the aryl group is phenyl or naphthyl. In another embodiment, the aryl group is phenyl.

[0107] The term "halo" or "halogen" as used herein by itself or as part of another group refers to -Cl, -F, -Br, or -I.

[0108] The term "nitro" as used herein by itself or as part of another group refers to -NO2.

[0109] The term "cyano" as used herein by itself or as part of another group refers to -CN.

[0110] The term "hydroxy" as herein used by itself or as part of another group refers to -OH.[OHl] The term "amino" as used by itself or as part of another group refers to a radical of the formula -NRlgRlh, wherein Rlgand Rlhare independently hydrogen or alkyl.

[0112] In one embodiment, the amino is -NH2.

[0113] In another embodiment, the amino is an "alkylamino," i.e., an amino group wherein Rlgis Ci-Ce alkyl and Rlhis hydrogen. In one embodiment, Rlgis C1-C4 alkyl. Non-limiting exemplary alkylamino groups include -N(H)CH3 and -N(H)CH2CH3.

[0114] In another embodiment, the amino is a "dialkylamino," i.e., an amino group wherein Rlgand Rlhare each independently Ci-Ce alkyl. In one embodiment, Rlgand Rlhare each independently C1-C4 alkyl. Non-limiting exemplary dialkylamino groups include -N(CH3)2and -N(CH3)CH2CH(CH3)2.

[0115] 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.

[0116] The term "haloalkyl" as used herein by itself or as part of another group refers to an alkyl substituted by one or more fluorine, chlorine, bromine, and / or iodine atoms. In one embodiment, the alkyl is substituted by one, two, or three fluorine and / or chlorine atoms. In another embodiment, the alkyl is substituted by one, two, or three fluorine atoms. In another embodiment, the alkyl is a Ci-Ce alkyl and the resulting haloalkyl is referred to as a "Ci-Ce haloalkyl." In another embodiment, the alkyl is a C1-C4 alkyl and the resulting haloalkyl is referred to as a "C1-C4 haloalkyl." In another embodiment, the alkyl group is a Ci or C2 alkyl. Non-limiting exemplary haloalkyl groups include 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.

[0117] 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-C4alkoxy." Non-limiting exemplary alkoxy groups include methoxy, ethoxy, and tertbutoxy.

[0118] 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.

[0119] The term "arylthio" as used herein by itself or as part of another group refers to an aryl group attached to a terminal sulfur atom. In some embodiments, the aryl is group is phenyl or naphthyl.

[0120] 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.

[0121] 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.

[0122] The term "heterocyclo" as used herein by itself or as part of another group refers to saturated and partially unsaturated, e.g., containing one or two double bonds, monocyclic, bicyclic, or tricyclic groups containing three to eighteen ring members, i.e., a 3- to 18-membered heterocyclo, comprising one, two, three, or four heteroatoms. Eachheteroatom 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.

[0123] The term "optionally substituted heterocyclo" as used herein by itself or part of another group refers to a heterocyclo group that is either unsubstituted or substituted with one to four substituents, wheren the substituents are each independently halo, nitro, cyano, hydroxyl, amino, (e.g., -NH2, alkylamino, or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl, or cycloalkyl.

[0124] The term "heteroaryl" as used herein by itself or as part of another group refers to monocyclic aromatic ring systems having five to six ring members, i.e., a 5- to 6-membered heteroaryl, comprising one, two, three, four, or five heteroatoms. Each heteroatom is independently oxygen, sulfur, or nitrogen. In one embodiment, the heteroaryl has three heteroatoms. In another embodiment, the heteroaryl has two heteroatoms. In another embodiment, the heteroaryl has one heteroatom. In another embodiment, the heteroaryl has 5 ring atoms, e.g., furyl, a 5-membered heteroaryl having four carbon atoms and one oxygen atom. In another embodiment, the heteroaryl has 6 ring atoms, e.g., pyridyl, a 6-membered heteroaryl having five carbon atoms and one nitrogen atom. Non-limiting exemplary heteroaryl groups include thienyl, furyl, pyranyl, 2 / 7-pyrrolyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, thiazolyl, isothiazolyl, and isoxazolyl. In one embodiment, the heteroaryl is chosen from thienyl (e.g., thien-2-yl and thien-3-yl), furyl (e.g., 2-furyl and 3-furyl), pyrrolyl (e.g., 1H- pyrrol-2-yl and lH-pyrrol-3-yl), imidazolyl (e.g., 2H-imidazol-2-yl and 2H-imidazol-4- yl), pyrazolyl (e.g., lH-pyrazol-3-yl, lH-pyrazol-4-yl, and lH-pyrazol-5-yl), pyridyl (e.g., pyridin-2-yl, pyridin-3-yl, and pyridin-4-yl), pyrimidinyl (e.g., pyrimidin-2-yl, pyrimidin-4-yl, and pyrimidin-5-yl), thiazolyl (e.g., thiazol-2-yl, thiazol-4-yl, and thiazol-5-yl), isothiazolyl (e.g., isothiazol-3-yl, isothiazol-4-yl, and isothiazol-5-yl), oxazolyl (e.g., oxazol-2-yl, oxazol-4-yl, and oxazol-5-yl) and isoxazolyl (e.g., isoxazol-3-yl, isoxazol-4- yl, and isoxazol-5-yl). The term heteroaryl also includes N-oxides. A non-limiting exemplary N-oxide is pyridyl N-oxide.

[0125] 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.

[0126] 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).

[0127] The term "chiral center" or "asymmetric carbon atom" refers to a carbon atom to which four different groups are attached.

[0128] 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.

[0129] The term "racemic" refers to a mixture of equal parts of enantiomers and which mixture is optically inactive.

[0130] 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.

[0131] 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.

[0132] 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 ofenantiomers 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.

[0133] 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.

[0134] Salts and solvates, e.g., hydrates, of the Compounds of the Disclosure can also be used in the methods disclosed herein.

[0135] 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.

[0136] 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.

[0137] 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, then cooling the solution at a rate sufficient to form crystals, and isolating the crystals by known methods, e.g., filtration. Analytical techniques such as infrared spectroscopy can be used to confirm the presence of the solvent in a crystal of the solvate.

[0138] 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 shouldbe construed as indicating any non-claimed element as essential to the practice of the disclosure.

[0139] 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).

[0140] 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.

[0141] 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 1 kg of the compound and 1 kg of carbon black is 50 wt / wt % (1 kg / 2 kg = 0.50 x 100 = 50 wt / wt %). The wt / wt % of a Compound of the Disclosure in a composition comprising 1 kg of the compound, 1 kg natural rubber, 2 kg of synthetic rubber, and 1 kg of carbon black is 20 wt / wt % (1 kg / 5 kg = 0.20 x 100 = 20 wt / wt %). The wt / wt % of natural rubber in a blend of one or more elastomers comprising 20 kg natural rubber and 30 kg synthetic rubber is 40 wt / wt % (20 kg / 50 kg = 0.40 x 100 = 40 wt / wt %).

[0142] As used herein, the term "masterbatch" refers to a composition comprising at least one elastomer and a Compound of the Disclosure. In some embodiments, the masterbatch comprises from about 5 wt / wt % to about 95 wt / wt % of at least one elastomer and from about 5 wt / wt % to about 95 wt / wt % of a Compound of the Disclosure. In some embodiments, the masterbatch comprises about 5 wt / wt %, about 10 wt / wt %, about 15 wt / wt %, about 20 wt / wt %, about 25 wt / wt %, about 30 wt / wt %, about 35 wt / wt %, about 40 wt / wt %, about 45 wt / wt %, about 50 wt / wt %, about 55 wt / wt %, about 60wt / wt %, about 65 wt / wt %, about 70 wt / wt %, about 75 wt / wt %, about 80 wt / wt %, about 85 wt / wt %, about 90 wt / wt %, or about 95 wt / wt % of a Compound of the Disclosure. In some embodiments, the masterbatch comprises about 5 wt / wt %, about 10 wt / wt %, about 15 wt / wt %, about 20 wt / wt %, about 25 wt / wt %, about 30 wt / wt %, about 35 wt / wt %, about 40 wt / wt %, about 45 wt / wt %, about 50 wt / wt %, about 55 wt / wt %, about 60 wt / wt %, about 65 wt / wt %, about 70 wt / wt %, about 75 wt / wt %, about 80 wt / wt %, about 85 wt / wt %, about 90 wt / wt %, or about 95 wt / wt % of at least one elastomer.

[0143] As used herein, the term "premix" refers to a composition comprising a Compound of the Disclosure and at least one additional component, e.g., a filler, a rubber chemical, a plasticizer, an additional anti degradant, or a combination thereof. In some embodiments, the premix does not comprise an elastomer. In some embodiments, the premix comprises from about 5 wt / wt % to about 95 wt / wt % of a Compound of the Disclosure and from about 5 wt / wt % to about 95 wt / wt % of the least one additional component, e.g., a filler, a rubber chemical, a plasticizer, an additional anti degradant, or a combination thereof. In some embodiments, the premix comprises about 5 wt / wt %, about 10 wt / wt %, about 15 wt / wt %, about 20 wt / wt %, about 25 wt / wt %, about 30 wt / wt %, about 35 wt / wt %, about 40 wt / wt %, about 45 wt / wt %, about 50 wt / wt %, about 55 wt / wt %, about 60 wt / wt %, about 65 wt / wt %, about 70 wt / wt %, about 75 wt / wt %, about 80 wt / wt %, about 85 wt / wt %, about 90 wt / wt %, or about 95 wt / wt % of a Compound of the Disclosure. In some embodiments, the premix comprises about 5 wt / wt %, about 10 wt / wt %, about 15 wt / wt %, about 20 wt / wt %, about 25 wt / wt %, about 30 wt / wt %, about 35 wt / wt %, about 40 wt / wt %, about 45 wt / wt %, about 50 wt / wt %, about 55 wt / wt %, about 60 wt / wt %, about 65 wt / wt %, about 70 wt / wt %, about 75 wt / wt %, about 80 wt / wt %, about 85 wt / wt %, about 90 wt / wt %, or about 95 wt / wt % of at least one additional component, e.g., a filler, a rubber chemical, a plasticizer, an additional anti degradant, or a combination thereof.

[0144] 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 to10. 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

[0145] 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.

[0146] In some embodiments, the composition comprises from about 0.1 wt / wt% to about 10 wt / wt% of the Compound of the Disclosure, e.g., from about 0.1 wt / wt% to about 0.5 wt / wt%, from about 0.1 wt / wt% to about 1 wt / wt%, from about 0.1 wt / wt% to about 1.5 wt / wt%, from about 0.1 wt / wt% to about 2 wt / wt%, from about 0.1 wt / wt% to about 2.5 wt / wt%, from about 0.1 wt / wt% to about 3 wt / wt%, from about 0.1 wt / wt% to about 3.5 wt / wt%, from about 0.1 wt / wt% to about 4 wt / wt%, from about 0.1 wt / wt% to about 4.5 wt / wt%, from about 0.1 wt / wt% to about 5 wt / wt%, from about 0.1 wt / wt% to about 6 wt / wt%, from about 0.1 wt / wt% to about 7 wt / wt%, from about 0.1 wt / wt% to about 8 wt / wt%, from about 0.1 wt / wt% to about 9 wt / wt%, from about 0.1 wt / wt% to about 10 wt / wt%, from about 0.5 wt / wt% to about 1 wt / wt%, from about 0.5 wt / wt% to about 1.5 wt / wt%, from about 0.5 wt / wt% to about 2 wt / wt%, from about 0.5 wt / wt% to about 2.5 wt / wt%, from about 0.5 wt / wt% to about 3 wt / wt%, from about 0.5 wt / wt% to about 3.5 wt / wt%, from about 0.5 wt / wt% to about 4 wt / wt%, from about 0.5 wt / wt% to about 4.5 wt / wt%, from about 0.5 wt / wt% to about 5 wt / wt%, from about 0.5 wt / wt% to about 6 wt / wt%, from about 0.5 wt / wt% to about 7 wt / wt%, from about 0.5 wt / wt% to about 8 wt / wt%, from about 0.5 wt / wt% to about 9 wt / wt%, from about 0.5 wt / wt% to about 10 wt / wt%, from about 1 wt / wt% to about 2 wt / wt%, from about 1 wt / wt% to about 2.5 wt / wt%, from about 1 wt / wt% to about 3 wt / wt%, from about 1 wt / wt% to about 3.5 wt / wt%, from about 1 wt / wt% to about 4 wt / wt%, from about 1 wt / wt% to about 4.5wt / wt%, from about 1 wt / wt% to about 5 wt / wt%, from about 1 wt / wt% to about 6 wt / wt%, from about 1 wt / wt% to about 7 wt / wt%, from about 1 wt / wt% to about 8 wt / wt%, from about 1 wt / wt% to about 9 wt / wt%, from about 1 wt / wt% to about 10 wt / wt%, from about 1.5 wt / wt% to about 2 wt / wt%, from about 1.5 wt / wt% to about 2.5 wt / wt%, from about 1.5 wt / wt% to about 3 wt / wt%, from about 1.5 wt / wt% to about 3.5 wt / wt%, from about 1.5 wt / wt% to about 4 wt / wt%, from about 1.5 wt / wt% to about 4.5 wt / wt%, from about 1.5 wt / wt% to about 5 wt / wt%, from about 1.5 wt / wt% to about 6 wt / wt%, from about 1.5 wt / wt% to about 7 wt / wt%, from about 1.5 wt / wt% to about 8 wt / wt%, from about 1.5 wt / wt% to about 9 wt / wt%, from about 1.5 wt / wt% to about 10 wt / wt%, from about 2 wt / wt% to about 2.5 wt / wt%, from about 2 wt / wt% to about 3 wt / wt%, from about 2 wt / wt% to about 3.5 wt / wt%, from about 2 wt / wt% to about 4 wt / wt%, from about 2 wt / wt% to about 4.5 wt / wt%, from about 2 wt / wt% to about 5 wt / wt%, from about 2 wt / wt% to about 6 wt / wt%, from about 2 wt / wt% to about 7 wt / wt%, from about 2 wt / wt% to about 8 wt / wt%, from about 2 wt / wt% to about 9 wt / wt%, from about 2 wt / wt% to about 10 wt / wt%, from about 2.5 wt / wt% to about 3 wt / wt%, from about 2.5 wt / wt% to about 3.5 wt / wt%, from about 2.5 wt / wt% to about 4 wt / wt%, from about 2.5 wt / wt% to about 4.5 wt / wt%, from about 2.5 wt / wt% to about 5 wt / wt%, from about 2.5 wt / wt% to about 6 wt / wt%, from about 2.5 wt / wt% to about 7 wt / wt%, from about 2.5 wt / wt% to about 8 wt / wt%, from about 2.5 wt / wt% to about 9 wt / wt%, from about 2.5 wt / wt% to about 10 wt / wt%, from about 3 wt / wt% to about 4 wt / wt%, from about 3 wt / wt% to about 4.5 wt / wt%, from about 3 wt / wt% to about 5 wt / wt%, from about 3 wt / wt% to about 6 wt / wt%, from about 3 wt / wt% to about 7 wt / wt%, from about 3 wt / wt% to about 8 wt / wt%, from about 3 wt / wt% to about 9 wt / wt%, from about 3 wt / wt% to about 10 wt / wt%, from about 3.5 wt / wt% to about 4 wt / wt%, from about 3.5 wt / wt% to about 4.5 wt / wt%, from about 3.5 wt / wt% to about 5 wt / wt%, from about 3.5 wt / wt% to about 6 wt / wt%, from about 3.5 wt / wt% to about 7 wt / wt%, from about 3.5 wt / wt% to about 8 wt / wt%, from about 3.5 wt / wt% to about 9 wt / wt%, from about 3.5 wt / wt% to about 10 wt / wt%, from about 4 wt / wt% to about 4.5 wt / wt%, from about 4 wt / wt% to about 5 wt / wt%, from about 4 wt / wt% to about 6 wt / wt%, from about 4 wt / wt% to about 7 wt / wt%, from about 4 wt / wt% to about 8 wt / wt%, from about 4 wt / wt% to about 9 wt / wt%, from about 4 wt / wt% to about 10 wt / wt%, from about 4.5 wt / wt% to about 5 wt / wt%, from about 4.5 wt / wt% to about 6 wt / wt%, from about 4.5 wt / wt% to about 7 wt / wt%, from about 4.5 wt / wt% to about 8wt / 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.

[0147] In some embodiments, a Composition of the Disclosure comprises from about15 wt / wt % to about 85 wt / wt % of a Compound of the Disclosure. In some embodiments, the composition comprises from about 1 wt / wt % to about 5 wt / wt %, from about 1 wt / wt % to about 15 wt / wt %, from about 1 wt / wt % to about 25 wt / wt %, from about 1 wt / wt % to about 35 wt / wt %, from about 1 wt / wt % to about 45 wt / wt %, 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 %, fromabout 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.

[0148] 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.

[0149] In another embodiment, a Composition of the Disclosure comprises a Compound of the Disclosure and one or more elastomers.

[0150] 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 andinclude, 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.

[0151] 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).

[0152] 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.

[0153] In some embodiments, a Composition of the Disclosure comprises from about 15 wt / wt % to about 85 wt / wt % of one or more elastomers. In some embodiments, the composition comprises from about 1 wt / wt % to about 5 wt / wt %, from about 1 wt / wt % to about 15 wt / wt %, from about 1 wt / wt % to about 25 wt / wt %, from about 1 wt / wt % to about 35 wt / wt %, from about 1 wt / wt % to about 45 wt / wt %, from about 1 wt / wt % to about 55 wt / wt %, from about 1 wt / wt % to about 65 wt / wt %, from about 1 wt / wt % to about 75 wt / wt %, from about 1 wt / wt % to about 85 wt / wt %, from about 1 wt / wt % to about 95 wt / wt %, from about 5 wt / wt % to about 15 wt / wt %, from about 5 wt / wt % to about 25 wt / wt %, from about 5 wt / wt % to about 35 wt / wt %, from about 5 wt / wt % to about 45 wt / wt %, from about 5 wt / wt % to about 55 wt / wt %, from about 5 wt / wt % to about 65 wt / wt %, from about 5 wt / wt % to about 75 wt / wt %, from about 5 wt / wt % to about 85 wt / wt %, from about 5 wt / wt % to about 95 wt / wt %, from about 15 wt / wt % to about 25 wt / wt %, from about 15 wt / wt % to about 35 wt / wt %, from about 15 wt / wt % to about 45 wt / wt %, from about 15 wt / wt % to about 55 wt / wt %, from about 15 wt / wt % to about 65 wt / wt %, from about 15 wt / wt % to about 75 wt / wt %, from about 15 wt / wt % to about 95 wt / wt %, from about 25 wt / wt % to about 35 wt / wt %, from about 25 wt / wt % to about 45 wt / wt %, from about 25 wt / wt % to about 55 wt / wt %, from about 25 wt / wt % to about 65 wt / wt %, from about 25 wt / wt % to about 75 wt / wt %, from about 25 wt / wt % to about 85 wt / wt %, from about 25 wt / wt % to about 95 wt / wt %, from about 35 wt / wt % toabout 45 wt / wt %, from about 35 wt / wt % to about 55 wt / wt %, from about 35 wt / wt % to about 65 wt / wt %, from about 35 wt / wt % to about 75 wt / wt %, from about 35 wt / wt % to about 85 wt / wt %, from about 35 wt / wt % to about 95 wt / wt %, from about 45 wt / wt % to about 55 wt / wt %, from about 45 wt / wt % to about 65 wt / wt %, from about 45 wt / wt % to about 75 wt / wt %, from about 45 wt / wt % to about 85 wt / wt %, from about 45 wt / wt % to about 95 wt / wt %, from about 55 wt / wt % to about 65 wt / wt %, from about 55 wt / wt % to about 75 wt / wt %, from about 55 wt / wt % to about 85 wt / wt %, from about 55 wt / wt % to about 95 wt / wt %, from about 65 wt / wt % to about 75 wt / wt %, from about 65 wt / wt % to about 85 wt / wt %, from about 65 wt / wt % to about 95 wt / wt %, from about 75 wt / wt % to about 85 wt / wt %, from about 75 wt / wt % to about 95 wt / wt %, or from about 85 wt / wt % to about 95 wt / wt % of one or more elastomers.

[0154] In some embodiments, a Composition of the Disclosure comprises about 50 wt / wt % of one or more elastomers. In some embodiments, the composition comprises about 1 wt / wt %, about 5 wt / wt %, about 10 wt / wt %, about 15 wt / wt %, about 20 wt / wt %, about 25 wt / wt %, about 30 wt / wt %, about 35 wt / wt %, about 40 wt / wt %, about 45 wt / wt %, about 55 wt / wt %, about 60 wt / wt %, about 65 wt / wt %, about 70 wt / wt %, about 75 wt / wt %, about 80 wt / wt %, about 85 wt / wt %, about 90 wt / wt %, or about 95 wt / wt % of one or more elastomers.

[0155] 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.

[0156] 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, fromabout 1 phr to about 20 phr, from about 2 phr to about 3 phr, from about 2 phr to about 4 phr, from about 2 phr to about 5 phr, from about 2 phr to about 7.5 phr, from about 2 phr to about 10 phr, from about 2 phr to about 20 phr, from about 3 phr to about 4 phr, from about 3 phr to about 5 phr, from about 3 phr to about 7.5 phr, from about 3 phr to about 10 phr, from about 3 phr to about 20 phr, from about 4 phr to about 5 phr, from about 4 phr to about 7.5 phr, from about 4 phr to about 10 phr, from about 4 phr to about 20 phr, from about 5 phr to about 7.5 phr, from about 5 phr to about 10 phr, from about 5 phr to about 20 phr, from about 7.5 phr to about 10 phr, from about 7.5 phr to about 20 phr, or from about 10 phr to about 20 phr of a Compound of the Disclosure.

[0157] 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.

[0158] In some embodiments, a Composition of the Disclosure comprises a Compound of the Disclosure and one or more fillers.

[0159] 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.

[0160] In some embodiments, the filler is derived from natural sources. For example, silica may be derived from rice husks.

[0161] 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 % toabout 45 wt / wt %, from about 5 wt / wt % to about 55 wt / wt %, from about 5 wt / wt % to about 65 wt / wt %, from about 5 wt / wt % to about 75 wt / wt %, from about 5 wt / wt % to about 85 wt / wt %, from about 5 wt / wt % to about 95 wt / wt %, from about 15 wt / wt % to about 25 wt / wt %, from about 15 wt / wt % to about 35 wt / wt %, from about 15 wt / wt % to about 45 wt / wt %, from about 15 wt / wt % to about 55 wt / wt %, from about 15 wt / wt % to about 65 wt / wt %, from about 15 wt / wt % to about 75 wt / wt %, from about 15 wt / wt % to about 95 wt / wt %, from about 25 wt / wt % to about 35 wt / wt %, from about 25 wt / wt % to about 45 wt / wt %, from about 25 wt / wt % to about 55 wt / wt %, from about 25 wt / wt % to about 65 wt / wt %, from about 25 wt / wt % to about 75 wt / wt %, from about 25 wt / wt % to about 85 wt / wt %, from about 25 wt / wt % to about 95 wt / wt %, from about 35 wt / wt % to about 45 wt / wt %, from about 35 wt / wt % to about 55 wt / wt %, from about 35 wt / wt % to about 65 wt / wt %, from about 35 wt / wt % to about 75 wt / wt %, from about 35 wt / wt % to about 85 wt / wt %, from about 35 wt / wt % to about 95 wt / wt %, from about 45 wt / wt % to about 55 wt / wt %, from about 45 wt / wt % to about 65 wt / wt %, from about 45 wt / wt % to about 75 wt / wt %, from about 45 wt / wt % to about 85 wt / wt %, from about 45 wt / wt % to about 95 wt / wt %, from about 55 wt / wt % to about 65 wt / wt %, from about 55 wt / wt % to about 75 wt / wt %, from about 55 wt / wt % to about 85 wt / wt %, from about 55 wt / wt % to about 95 wt / wt %, from about 65 wt / wt % to about 75 wt / wt %, from about 65 wt / wt % to about 85 wt / wt %, from about 65 wt / wt % to about 95 wt / wt %, from about 75 wt / wt % to about 85 wt / wt %, from about 75 wt / wt % to about 95 wt / wt %, or from about 85 wt / wt % to about 95 wt / wt % of one or more fillers.

[0162] 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.

[0163] In some embodiments, a Composition of the Disclosure comprises from about 30 phr to about 500 phr of one or more fillers. In some embodiments, the composition comprises from about 30 phr to about 50 phr, from about 30 phr to about 100 phr, from about 30 phr to about 150 phr, from about 30 phr to about 200 phr, from about 30 phr to about 250 phr, from about 30 phr to about 300 phr, from about 30 phr to about 350 phr,from about 30 phr to about 400 phr, from about 30 phr to about 450 phr, from about 30 phr to about 500 phr, from about 50 phr to about 100 phr, from about 50 phr to about 150 phr, from about 50 phr to about 200 phr, from about 50 phr to about 250 phr, from about 50 phr to about 300 phr, from about 50 phr to about 350 phr, from about 50 phr to about 400 phr, from about 50 phr to about 450 phr, from about 50 phr to about 500 phr, from about 100 phr to about 150 phr, from about 100 phr to about 200 phr, from about 100 phr to about 250 phr, from about 100 phr to about 300 phr, from about 100 phr to about 350 phr, from about 100 phr to about 400 phr, from about 100 phr to about 450 phr, from about 100 phr to about 500 phr, from about 150 phr to about 200 phr, from about 150 phr to about 250 phr, from about 150 phr to about 300 phr, from about 150 phr to about 350 phr, from about 150 phr to about 400 phr, from about 150 phr to about 450 phr, from about 150 phr to about 500 phr, from about 200 phr to about 250 phr, from about 200 phr to about 300 phr, from about 200 phr to about 350 phr, from about 200 phr to about 400 phr, from about 200 phr to about 450 phr, from about 200 phr to about 500 phr, from about 250 phr to about 300 phr, from about 250 phr to about 350 phr, from about 250 phr to about 400 phr, from about 250 phr to about 450 phr, from about 250 phr to about 500 phr, from about 300 phr to about 350 phr, from about 300 phr to about 400 phr, from about 300 phr to about 450 phr, from about 300 phr to about 500 phr, from about 350 phr to about 400 phr, from about 350 phr to about 450 phr, from about 350 phr to about 500 phr, from about 400 phr to about 450 phr, from about 400 phr to about 500 phr, or from about 450 phr to about 500 phr of one or more fillers.

[0164] 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.

[0165] 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.

[0166] 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.

[0167] 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.

[0168] 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 includedimethylcarbamothioic 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).

[0169] 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.

[0170] 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.

[0171] 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 % toabout 25 wt / wt %, from about 15 wt / wt % to about 35 wt / wt %, from about 15 wt / wt % to about 45 wt / wt %, from about 15 wt / wt % to about 55 wt / wt %, from about 15 wt / wt % to about 65 wt / wt %, from about 15 wt / wt % to about 75 wt / wt %, from about 15 wt / wt % to about 95 wt / wt %, from about 25 wt / wt % to about 35 wt / wt %, from about 25 wt / wt % to about 45 wt / wt %, from about 25 wt / wt % to about 55 wt / wt %, from about 25 wt / wt % to about 65 wt / wt %, from about 25 wt / wt % to about 75 wt / wt %, from about 25 wt / wt % to about 85 wt / wt %, from about 25 wt / wt % to about 95 wt / wt %, from about 35 wt / wt % to about 45 wt / wt %, from about 35 wt / wt % to about 55 wt / wt %, from about 35 wt / wt % to about 65 wt / wt %, from about 35 wt / wt % to about 75 wt / wt %, from about 35 wt / wt % to about 85 wt / wt %, from about 35 wt / wt % to about 95 wt / wt %, from about 45 wt / wt % to about 55 wt / wt %, from about 45 wt / wt % to about 65 wt / wt %, from about 45 wt / wt % to about 75 wt / wt %, from about 45 wt / wt % to about 85 wt / wt %, from about 45 wt / wt % to about 95 wt / wt %, from about 55 wt / wt % to about 65 wt / wt %, from about 55 wt / wt % to about 75 wt / wt %, from about 55 wt / wt % to about 85 wt / wt %, from about 55 wt / wt % to about 95 wt / wt %, from about 65 wt / wt % to about 75 wt / wt %, from about 65 wt / wt % to about 85 wt / wt %, from about 65 wt / wt % to about 95 wt / wt %, from about 75 wt / wt % to about 85 wt / wt %, from about 75 wt / wt % to about 95 wt / wt %, or from about 85 wt / wt % to about 95 wt / wt % of one or more rubber chemicals.

[0172] 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.

[0173] 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.

[0174] 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.

[0175] 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.

[0176] In some embodiments, a Composition of the Disclosure comprises from about15 wt / wt % to about 85 wt / wt % of one or more plasticizers. In some embodiments, the composition comprises from about 1 wt / wt % to about 5 wt / wt %, from about 1 wt / wt % to about 15 wt / wt %, from about 1 wt / wt % to about 25 wt / wt %, from about 1 wt / wt % to about 35 wt / wt %, from about 1 wt / wt % to about 45 wt / wt %, from about 1 wt / wt % to about 55 wt / wt %, from about 1 wt / wt % to about 65 wt / wt %, from about 1 wt / wt % to about 75 wt / wt %, from about 1 wt / wt % to about 85 wt / wt %, from about 1 wt / wt % to about 95 wt / wt %, from about 5 wt / wt % to about 15 wt / wt %, from about 5 wt / wt % to about 25 wt / wt %, from about 5 wt / wt % to about 35 wt / wt %, from about 5 wt / wt % to about 45 wt / wt %, from about 5 wt / wt % to about 55 wt / wt %, from about 5 wt / wt % to about 65 wt / wt %, from about 5 wt / wt % to about 75 wt / wt %, from about 5 wt / wt % toabout 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.

[0177] 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.

[0178] 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, fromabout 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.

[0179] 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.

[0180] 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), 7V1-phenyl-A4-(propan-2- yl)benzene-l,4-diamine (IPPD), A( '-di -scc-butyl - -phenylenedi amine (44PD), N,N'~ bis(l,3-dimethylbutyl)-p-phenylenediamine (66PD), 7V,A-bis(l,4-dimethylpentyl)-p- phenylenediamine (77PD), and N-N'-dioctyl- -phenylenediamine (88PD). Non-limiting examples of TMQs include 2,2,4-trimethyl-l,2-dihydroquinoline and oligomers or polymers thereof.

[0181] 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 someembodiments, 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.

[0182] 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 70wt / 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.

[0183] 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.

[0184] 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.

[0185] 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.

[0186] 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.

[0187] 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.

[0188] 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.

[0189] The present disclosure also provides lubricant compositions comprising a Compound of the Disclosure and a lubricant. Non-limiting examples of lubricantsinclude 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.

[0190] 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.

[0191] 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.

[0192] In some embodiments, the present disclosure provides a composition recited in Table 2.Table 2

[0193] In some embodiments, the vulcanized tire or other rubber article composition of Table 2 comprises about 0.1 wt / wt %, about 0.2 wt / wt %, about 0.3 wt / wt %, about 0.4 wt / wt %, about 0.5 wt / wt %, about 0.6 wt / wt %, about 0.7 wt / wt %, about 0.8 wt / wt %, about 0.9 wt / wt %, about 1 wt / wt %, about 2 wt / wt %, about 3 wt / wt %, about 4 wt / wt %, about 5 wt / wt %, about 6 wt / wt %, about 7 wt / wt %, about 8 wt / wt %, about 9 wt / wt %, or about 10 wt / wt % of a Compound of the Disclosure. In some embodiments, the vulcanized tire or other rubber article of Table 2 comprises comprises about 5 wt / wt %, about 10 wt / wt %, about 15 wt / wt %, about 20 wt / wt %, about 25 wt / wt %, about 30 wt / wt %, about 35 wt / wt %, about 40 wt / wt %, about 45 wt / wt %, about 50 wt / wt %, about 55 wt / wt %, about 60 wt / wt %, about 65 wt / wt %, about 70 wt / wt %, about 75 wt / wt %, about 80 wt / wt %, about 85 wt / wt %, about 90 wt / wt %, or about 95 wt / wt % of at least one elastomer.

[0194] In some embodiments, the unvulcanized in-tire component or built up component or other end use component composition of Table 2 comprises about 0.01 wt / wt %, about 0.02 wt / wt %, about 0.03 wt / wt %, about 0.04 wt / wt %, about 0.05 wt / wt %, about 0.06 wt / wt %, about 0.07 wt / wt %, about 0.08 wt / wt %, about 0.09 wt / wt %, about 0.1 wt / wt %, about 0.2 wt / wt %, about 0.3 wt / wt %, about 0.4 wt / wt %, about 0.5 wt / wt %, about 0.6 wt / wt %, about 0.7 wt / wt %, about 0.8 wt / wt %, about 0.9 wt / wt %, about 1 wt / wt %, about 2 wt / wt %, about 3 wt / wt %, about 4 wt / wt %, about 5 wt / wt %, about 6 wt / wt %, about 7 wt / wt %, about 8 wt / wt %, about 9 wt / wt %, or about 10 wt / wt % of a Compound of the Disclosure. In some embodiments, the unvulcanized in-tire component or built up component or other end use component composition of Table 2 comprises comprises about 5 wt / wt %, about 10 wt / wt %, about 15 wt / wt %, about 20 wt / wt %, about 25 wt / wt %, about 30 wt / wt %, about 35 wt / wt %, about 40 wt / wt %, about 45 wt / wt %, about 50wt / wt %, about 55 wt / wt %, about 60 wt / wt %, about 65 wt / wt %, about 70 wt / wt %, about 75 wt / wt %, about 80 wt / wt %, about 85 wt / wt %, about 90 wt / wt %, or about 95 wt / wt % of at least one elastomer.Vulcanized Elastomeric Articles

[0195] 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.

[0196] The present disclosure also provides vulcanized elastomeric articles prepared using a composition described herein.

[0197] 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.

[0198] 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.

[0199] 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

[0200] 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.

[0201] 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 toabout 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.

[0202] 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.

[0203] 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

[0204] 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 N-isopropyl-4,8-dimethyl-4-phenyl-l,2,3,4-tetrahydroquinolin-6-amine(Compound 1)Step 1AcetonitrileTrifluoroacetic acidintermediate compound 1-1

[0205] To a 1-L round bottom flask fitted with an overhead stirrer, a thermometer, and a reflux condenser was loaded 2-methyl-4-nitroaniline (30 g; 197 mmol) and acetonitrile (320 mL). The mixture was stirred under N2 protection. To the resulting clear yellow solution was added trifluoroacetic acid (16.0 mL; 209 mmol), aqueous 37% formaldehyde solution (26.0 mL; 349 mmol HCHO), and alpha-methylstyrene (46.0 mL; 354 mmol) in that order. The reaction mixture (slurry formed after formaldehyde was added) was refluxed for 2 hours (internal temperature = 77-78 °C), whereupon a clear yellow solution formed. Upon cooling to room temperature, aqueous 1 mol / L sodium bicarbonate (300 mL) was added by portions. The obtained 2-phase system was stirred until CO2 generation ceased, then transferred to a 2-L separatory funnel. Ethyl acetate (700 mL) was added. After shaking and decanting, the aqueous phase was discarded. The organic phase was washed with aqueous 1 mol / L sodium bisulfite (300 mL) and aqueous saturated sodium chloride (300 mL), dried over anhydrous magnesium sulfate, filtered, and stripped of volatiles under reduced pressure (rotary evaporator; water bath = 50 °C). The obtained dark oil (69.5 g) was diluted with a mixture of isopropanol (100 mL) and hexanes (20 mL). The mixture was swirled until homogenous then kept at -20 °C overnight whereupon a yellow solid separated. The yellow solid was collected by vacuum filtration (disposable 20-micron polyethylene frit) and washed with hexanes (50 mL) directly on the frit. The damp material was dried in the vacuum oven at 45-50 °C for a few hours, then at room temperature overnight, to yield 24.1 g of 4,8-dimethyl-6-nitro- 4-phenyl-l,2,3,4-tetrahydroquinoline (intermediate compound 1-1) as a yellow powder.Intermediate compound 1-1 was characterized byJH and13C nuclear magnetic resonance (NMR) spectroscopy, as shown in Figs. 1, and 2, respectively. LC-UV analysis indicated 93.4% purity at 260 nm detection, as shown in Fig. 3.Step 2intermediate compound 1-1 Compound 1

[0206] To a 300-mL Parr autoclave was loaded intermediate compound 1-1 (23.0 g; 81.5 mmol), 3% Pt / C sulfided (Johnson Matthey) (0.4077 g wet), isopropanol (201 mL), and acetone (10.4 mL; 142 mmol). The reaction mixture was stirred and heated to 120 °C under 250 PSI H2 for 1.5 hours. Upon cooling to room temperature, the mixture post reaction was filtered through inline 0.2-micron frit. The clave was rinsed with fresh isopropanol (approx. 200 mL) and the obtained mixture was filtered through the inline 0.2-micron frit. The combined filtrates were filtered through filter paper and stripped of their volatiles under reduced pressure (rotary evaporator; water bath = 50 °C). The obtained crude material (light-brown oil) weighed 23.7 g. Upon standing for several weeks at room temperature, the oil solidified as a dark solid mass. Upon cooling to -20 °C overnight, the solid mass was broken apart with a spatula. To the obtained dark powder was added a mixture of ethyl acetate and hexanes (10 mL and 51 mL respectively). The obtained slurry was magnetically stirred at room temperature under N2 protection for 4 days. The solid was collected by vacuum filtration over disposable polyethylene 0.2-micron frit and rinsed quickly with several portions of hexanes (50 mL total). The damp powder (16.58 g) was dried under vacuum at 50-60 °C for a few hours, then at room temperature overnight, to yield 14.48 g of N-isopropyl-4,8-dimethyl-4- phenyl-l,2,3,4-tetrahydroquinolin-6-amine (Compound 1) (60% with respect to intermediate compound 1-1) as a light brown powder. Compound 1 was characterized by 13C NMR spectroscopy, as shown in Fig 4. LC-UV analysis indicated 96.5% purity at 260 nm detection, as shown in Fig. 5. Mass (m / z): 295.4 [M+l]+.EXAMPLE 2Synthesis of 4,8-dimethyl-N-(pentan-3-yl)-4-phenyl-l,2,3,4-tetrahydroquinolin-6-amine(Compound 2)HeatCompound 2

[0207] To a 300-mL Parr autoclave was loaded intermediate compound 1-1 (12.0 g; 42.5 mmol), 3% Pt / C sulfided (Johnson Matthey) (0.42 g wet), 3-pentanone (180 mL; 1.70 mol) and aqueous 5 wt% phosphoric acid (1.8 g solution; 0.92 mmol H3PO4). The reaction mixture was stirred and heated to 150 °C under 250 PSI H2 for 2 hours. Upon cooling to room temperature, the mixture post reaction was filtered through inline 0.2- micron frit. The clave was rinsed with isopropanol (approx. 150-200 mL) and the obtained mixture was filtered through the inline 0.2-micron frit. The combined filtrates were stripped of their volatiles under reduced pressure (rotary evaporator; water bath = 50 °C). The obtained residue was dissolved in hexanes (14 mL) whereupon trace amounts of insoluble material separated. The mixture was vacuum filtered over Celite S and the cake was rinsed with hexanes (100 mL). The combined filtrates were stripped of their volatiles under reduced pressure (rotary evaporator; water bath = 50 °C). Drying under vacuum at 60 °C overnight yielded 12.5 g of a brown oil which darkened over time upon standing at room temperature to afford 4,8-dimethyl-N-(pentan-3-yl)-4-phenyl-l,2,3,4- tetrahydroquinolin-6-amine (Compound 2). Compound 2 was characterized by13C NMR spectroscopy, as shown in Fig 6. LC-UV analysis indicated 91.0% purity at 260 nm detection, as shown in Fig. 7. Mass (m / z): 323.4 [M+l]+.EXAMPLE 3Synthesis of N-isopropyl-4,8-dimethyl-2,4-diphenyl-l,2,3,4-tetrahydroquinolin-6-amine (Compound 3)Step 1intermediate compound 3-1

[0208] To a 1-L round bottom flask fitted with a stir-bar, a thermometer, and a reflux condenser was loaded 2-methyl-4-nitroaniline (9.96 g; 65.5 mmol) and acetonitrile (200 mL). The mixture was stirred under N2 protection. To the resulting clear yellow solution was added trifluoroacetic acid (5.3 mL; 68.7 mmol), benzaldehyde (6.6 mL; 65.5 mmol), and alpha-methylstyrene (15.3 mL; 117.9 mmol) in that order. The reaction mixture was heated to 82 °C (oil bath temperature) for 4 hours. Upon cooling to room temperature, a yellow precipitate formed. A solution of sodium bicarbonate (10 g) in deionized water (200 mL) was added by portions. Ethyl acetate (200 mL) was added in portions to dissolve the precipitate. The obtained 2-phase system was transferred to a separatory funnel. The aqueous phase was discarded. The organic phase was washed with a solution of sodium bisulfite (15.0 g) in deionized water (200 mL) and aqueous saturated sodium chloride (200 mL), dried over anhydrous magnesium sulfate, filtered, and stripped of volatiles under reduced pressure (rotary evaporator; water bath = 45 °C). The residue was dried under vacuum to 20 mbar at 45 deg C for 20 min. The resulting viscous orange oil was suspended in 1 : 1 v / v isopropanol: hexanes (100 mL) and heated to 55 °C for 15 minutes, upon which the orange oil became a yellow solid. The mixture was allowed to cool to room temperature, then filtered to isolate the yellow solid. The solid was washed with hexanes (3 x 20 mL) and dried over a vacuum filter for approx. 20 min to afford 15.2 g of 4,8-dimethyl-6-nitro-2,4-diphenyl-l,2,3,4-tetrahydroquinoline (intermediate compound 3-1) as a yellow powder. LC-UV analysis indicated 99.0% purity at 260 nm detection, as shown in Fig. 8.Step 2Isopropanol3% Pt / C - sulfided Pressurized H2Heatintermediate compound 3-1

[0209] To a 300-mL Parr autoclave was loaded intermediate compound 3-1 (10.6 g, 29.7 mmol), 3% Pt / C sulfided (Johnson Matthey) (0.2467 g wet), isopropanol (200 mL), and acetone (5.6 mL, 75.5 mmol). The reaction mixture was stirred and heated to 150 °C under 250 PSI Eb for 107 minutes. Upon cooling to room temperature, the mixture was filtered over inline 0.2-micron frit, the reactor was rinsed with 100 mL isopropanol, and the combined filtrates were removed under reduced pressure (rotary evaporator; water bath = 50 °C) to give a waxy beige solid (10.68 g). The solid was dried under vacuum for 16 hours at 55 °C to yield 9.27 g of N-isopropyl-4,8-dimethyl-2,4-diphenyl-l, 2,3,4- tetrahydroquinolin-6-amine (Compound 3) as a waxy beige solid. Compound 3 was characterized by13C NMR spectroscopy, as shown in Fig 9. LC-UV analysis indicated 94.5% purity at 260 nm detection, as shown in Fig. 10. Mass (m / z): 371.4 [M+l]+.EXAMPLE 4Synthesis of N,2-diisopropyl-4,8-dimethyl-4-phenyl-l,2,3,4-tetrahydroquinolin-6-amine (Compound 4)intermediate compound 4-1

[0210] To a 250-mL flask equipped with a stir-bar and a reflux condenser was loaded 2- methyl-4-nitroaniline (4.2 g; 27.6 mmol) and acetonitrile (50 mL). The mixture was stirred under N2 protection (2-methyl-4-nitroaniline dissolved within a few minutes). Tothe resulting dark solution were sequentially added trifluoroacetic acid (2.2 mL; 28.7 mmol), isobutyraldehyde (4.4 mL; 48 mmol), and alpha-methylstyrene (6.4 mL; 49.2 mmol) in that order. The reaction mixture was heated (oil bath set to 80 °C). Once the set temperature was reached, it was maintained for 5 hours. Upon cooling to room temperature (overnight), a solution of sodium bicarbonate (4.75 g; 56.5 mmol) in deionized water (60 mL) was portion-wise added. The obtained 2-phase system was stirred until CO2 generation ceased, Ethyl acetate was added (50 mL), then the mixture was transferred to a separatory funnel. The flask was rinsed with ethyl acetate (2 x 20 mL). The organic solutions were transferred to the separatory funnel. After decantation, the aqueous layer was discarded. The organic layer was washed with aq. saturated sodium bisulfite (30 mL), dried over MgSCh, filtered, and stripped of its volatiles under reduced pressure (rotary evaporator; water bath = 50 °C). No attempt was undertaken to strip excess alpha-methylstyrene (BP = 165-169 deg C). To the obtained impure orange oil weighing approx. 9.9 g was added a mixture of hexanes (20 mL) and isopropanol (10 mL). After swirling for a few seconds, the obtained solution was kept at -20 °C for 1 hour whereupon a yellow crystalline solid and a dark dense mass separated. Upon warming to room temperature and vigorous swirling, the dark mass vanished, and additional amounts of yellow crystals formed. The solid was collected by vacuum filtration over disposable polyethylene 0.2-micron frit and rinsed quickly with hexanes (10 mL). The damp solid (2.87 g) was dried under vacuum at 50-60 °C for a few hours, then at room temperature for a few hours, to afford 2.78 g of 2-isopropyl-4,8-dimethyl-6- nitro-4-phenyl-l,2,3,4-tetrahydroquinoline (intermediate compound 4-1) as a yellow powder. Intermediate compound 4-1 was characterized by13C NMR spectroscopy, as shown in Fig 11. LC-UV analysis indicated 95.2% purity at 260 nm detection, as shown in Fig. 12.Step 2Isopropanol3% Pt / C - sulfided Pressurized H2Heatintermediate compound 4-1 Compound 4

[0211] To a 300-mL Parr autoclave was loaded intermediate compound 4-1 (1.6 g; 4.93 mmol), 3% Pt / C sulfided (Johnson Matthey) (0.0366 g wet), isopropanol (130 mL), and acetone (0.99 mL; 13 mmol). The reaction mixture was stirred and heated to 150 °C under 250 PSI H2 for 65-70 minutes. Upon cooling to room temperature, the mixture post reaction was filtered through inline 0.2-micron frit. The clave was rinsed with fresh isopropanol (150 mL) and the obtained mixture was filtered through the inline 0.2-micron frit. The combined filtrates were stripped of volatiles under reduced pressure (rotary evaporator; water bath = 55 °C). The residue was dissolved in 40% ethyl acetate in hexanes (5 mL). The obtained solution was loaded into a 41 mm inner diameter column previously prepared with silica gel (ultrapure; 60 A; 60-200 pm) and 20% ethyl acetate in hexanes (height of silica = 10-11 cm). 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). The fractions having Rf = 0.3 were collected, combined, and stripped of their volatiles under reduced pressure (rotary evaporator; water bath = 55 °C). The obtained light-brown oil was dried under vacuum (rotary evaporator; water bath = 55 °C; <2 mbars) for 1.5 hours, then in a vacuum oven at 75-80 °C overnight, to yield 1.4 g N,2- diisopropyl-4,8-dimethyl-4-phenyl-l,2,3,4-tetrahydroquinolin-6-amine (Compound 4) as a transparent light orange very viscous oil. Compound 4 was characterized by13C NMR spectroscopy, as shown in Fig 13. LC-UV analysis indicated 97.2% purity at 260 nm detection, as shown in Fig. 14. Mass (m / z): 337.4 [M+l]+.EXAMPLE 5Synthesis of N-isopropyl-3,3,8-trimethyl-l,2,3,4-tetrahydroquinolin-6-amine (Compound 47)Step 1 lep-toluenesulfonicacid monohydrateintermediate compound 47-1

[0212] To a 100-mL flask equipped with a stir-bar and a reflux condenser was loaded 2- methyl-4-nitroaniline (3.96 g; 26.0 mmol) and acetonitrile (42 mL). The mixture was stirred under N2 blanket. To the obtained dark solution were sequentially added paratoluenesulfonic acid monohydrate (0.486 g; 2.56 mmol acid), aqueous 37% formaldehyde(2.4 mL; 32.2 mmol HCHO), and isobutyraldehyde (3.7 mL; 41 mmol). A yellow solid separated after addition of the formaldehyde solution. The reaction mixture was stirred without external cooling or heating for 2 days whereupon a dark solution was obtained. Sodium bicarbonate (0.337 g; 4.01 mmol) was added and the mixture was stirred for 5-10 minutes. Anhydrous magnesium sulfate was added and the obtained slurry was stirred for approx. 5 minutes. The insoluble materials were removed by gravimetric filtration over filter paper. The cake was rinsed with some acetonitrile. The filtrate was stripped of its volatiles under reduced pressure (rotary evaporator; water bath = 50 °C). The crude material (6.35 g of damp yellow-orange solid) was triturated in isopropanol (20 mL) with a spatula until all the solid had detached from the flask walls. The obtained slurry was magnetically stirred for 10-15 minutes. Hexanes (20 mL) was added and the mixture was magnetically stirred for 30 minutes. The solid was collected by vacuum filtration over disposable 0.2-micron polyethylene frit, and rinsed with several portions of hexanes (total = 25 mL). The damp solid was dried under vacuum at approx. 50 °C for a few hours then at room temperature overnight to afford 3.09 g of crude 3,3,8-trimethyl-6-nitro-l,2,3,4- tetrahydroquinolin-4-ol (intermediate compound 47-1) as a yellow powder. Crude intermediate compound 47-1 was characterized by13C APT NMR spectroscopy, as shown in Fig 15. LC-UV analysis indicated approx. 61% purity at 260 nm detection, as shown in Fig. 16. The crude material was involved in the subsequent step without further purification.Step 2Toluene3% Pt / C - sulfided Pressurized H2Heat intermediate compound 47-1 Compound 47

[0213] To a 300-mL Parr autoclave was loaded crude intermediate compound 47-1 (2.8 g; <11.9 mmol), toluene (140 mL), acetone (1.7 mL; 23.2 mmol), and 3% Pt / C sulfided (Johnson Matthey) (150 mg wet). The reaction mixture was stirred and heated to 120 °C under 250 PSI H2 for 2 hours. Upon cooling to room temperature, the mixture post reaction was filtered through inline 0.2-micron frit. The clave was rinsed withisopropanol (130 mL) and the obtained mixture was filtered through the inline 0.2-micron frit. The combined filtrates were stripped of volatiles under reduced pressure (rotary evaporator; water bath = 60 °C). The residue was dissolved in hexanes (4 mL). The obtained solution was loaded into a 41 mm inner diameter column previously prepared with silica gel (ultrapure; 60 A; 60-200 pm) and 30% ethyl acetate in hexanes (height of silica = 16-17 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 having Rf = 0.45 were collected, combined, and stripped of their volatiles under reduced pressure (rotary evaporator; water bath = 50 °C). The obtained light-brown oil was dried under vacuum (rotary evaporator; water bath = 55 °C; <8 mbars) for 1.5 hours to yield 0.96 g of N-isopropyl-3,3,8-trimethyl-l,2,3,4-tetrahydroquinolin-6-amine (Compound 47) as a brown oil. Compound 47 was characterized by13C APT NMR spectroscopy, as shown in Fig 17. LC-UV analysis indicated 94.6% purity at 260 nm detection, as shown in Fig. 18. Mass (m / z): 233.3 [M+l]+.EXAMPLE 6Oxidative Induction Time (OIT) Performance of Compounds of the Disclosure

[0214] 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.

[0215] 0.5 wt % of a Compound of the Disclosure, N1-(4-methylpentan-2-yl)-N4- 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 3. As indicated by the data in Table 3, Compounds of the Disclosure demonstrate antioxidant activity compared to the blank control.

[0216] The melting points of Compounds of the Disclosure were also measured and are listed in Table 3.Table 3

[0217] 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):(I), or a salt, solvate, or stereoisomer thereof, wherein:= is a single or a double bond;Rlais selected from the group consisting of optionally substituted C1-C12 alkyl, -CHRlcRld, C3-C6 cycloalkyl, 4- to 6-membered heterocyclyl, optionally substituted phenyl, 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 optionally substituted phenyl, C3-C6 cycloalkyl, and optionally substituted 5- or 6-membered heteroaryl;Rldis selected from the group consisting of hydrogen and C1-C9 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, -NHR4, -NR4R5, -OH, -SH, -SC(=O)R4, -SC(=O)SR4, -SC(=O)NHR4, -SC(=O)NR4R5, -NHC(=O)SR4, -NR4C(=O)SR5, -NHC(=S)SR4, - NR4C(=S)SR5, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl; orR2bis 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, -NHR4, -NR4R5, -OH, -SH, -SC(=O)R4, -SC(=O)SR4, -SC(=O)NHR4, -SC(=O)NR4R5, -NHC(=O)SR4, -NR4C(=O)SR5, -NHC(=S)SR4, - NR4C(=S)SR5, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl; andR2aand R2ctogether with the two carbon atoms to which they are attached form a C5-C8 cycloalkyl, a 5- to 8-membered heterocyclyl, or a Cs-Ce aryl;R3aand R3bare independently selected from the group consisting of hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl, with the proviso that if = is a double bond, R3bis absent; orR3aand R3btogether with the carbon atom to which they are attached form a C3-C12 cycloalkyl, with the proviso that = is a single bond;R3Cand R3dare independently selected from the group consisting of hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl, with the proviso that if = is a double bond, R3dis absent; orR3Cand R3dtogether with the carbon atom to which they are attached form a C3-C12 cycloalkyl, with the proviso that = is a single bond;R3eand R3fare independently selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, -OH, -SH, Ci-Cs alkoxy, Ci-Cs alkylthio, arylthio,C(=O)OR4, -OC(=O)R4, -C(=O)NR4R5, -NR4C(=O)R5, -NHR4, -NR4R5, -SC(=O)R4, -SC(=O)S R4, -SC(=O)NHR4, -SC(=O)NR4R5, -NHC(=O)SR4, -NR4C(=O)SR5, -NHC(=S)SR4, -NR4C(=S )SR5, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl, with the proviso that if R3eand / or R3fare hydrogen, R3cand R3dare independently selected from the group consisting of C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl; orR3eand R3ftaken together with the carbon atom to which they are attached form a C3-C12 cycloalkyl;R3gis selected from the group consisting of hydrogen and C1-C9 alkyl; andR4and R5are at each occurrence independently selected from the group consisting of hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl.

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

3. The compound of claim 2, or a salt, solvate, or stereoisomer thereof, wherein:R3Cand R3dare independently selected from the group consisting of C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl; orR3Cand R3dtogether with the carbon atom to which they are attached form a C3-C12 cycloalkyl.

4. The compound of claim 2 or 3, or a salt, solvate, or stereoisomer thereof, wherein:R3eand R3fare independently selected from the group consisting of halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, -OH, -SH, Ci-Cs alkoxy, Ci-Cs alkylthio, arylthio, C(=O)OR4, -OC(=O)R4, -C(=O)NR4R5, -NR4C(=O)R5, -NHR4, -NR4R5, -SC(=O)R4, -SC(=O)S R4, -SC(=O)NHR4, -SC(=O)NR4R5, -NHC(=O)SR4, -NR4C(=O)SR5, -NHC(=S)SR4, -NR4C(=S )SR5, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl; orR3eand R3ftaken together with the carbon atom to which they are attached form a C3-C12 cycloalkyl.

5. The compound of any one of claims 1-4, or a salt, solvate, or stereoisomer thereof, wherein R3bis hydrogen.

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

7. The compound of any one of claims 1-6, or a salt, solvate, or stereoisomer thereof, wherein Rlais optionally substituted phenyl.

8. The compound of any one of claims 1-6, or a salt, solvate, or stereoisomer thereof, wherein Rlais C1-C12 alkyl.

9. The compound of claim 8, or a salt, solvate, or stereoisomer thereof, wherein Rlais methyl, ethyl, propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, or nonyl.

10. The compound of claim 9, or a salt, solvate, or stereoisomer thereof, wherein Rlais iso-propyl or sec-butyl.

11. The compound of claim 8, or a salt, solvate, or stereoisomer thereof, wherein Rlais:

12. The compound of any one of claims 1-11, or a salt, solvate, or stereoisomer thereof, wherein R2a, R2b, and R2care independently selected from the group consisting of hydrogen and C1-C9 alkyl.

13. The compound of claim 12, or a salt, solvate, or stereoisomer thereof, wherein R2band R2Care hydrogen.

14. The compound of claim 13, or a salt, solvate, or stereoisomer thereof, wherein R2ais selected from the group consisting of hydrogen and C1-C4 alkyl.

15. The compound of any one of claims 1-14, or a salt, solvate, or stereoisomer thereof, wherein R3ais hydrogen.

16. The compound of any one of claims 1-14, or a salt, solvate, or stereoisomer thereof, wherein R3ais C1-C9 alkyl.

17. The compound of any one of claims 1-14, or a salt, solvate, or stereoisomer thereof, wherein R3ais C3-C6 cycloalkyl.

18. The compound of any one of claims 1-14, or a salt, solvate, or stereoisomer thereof, wherein R3ais optionally substituted phenyl.

19. The compound of any one of claims 1-18, or a salt, solvate, or stereoisomer thereof, wherein R3cis hydrogen.

20. The compound of any one of claims 1-18, or a salt, solvate, or stereoisomer thereof, wherein R3cis C1-C9 alkyl.

21. The compound of any one of claims 1-18, or a salt, solvate, or stereoisomer thereof, wherein R3cis C3-C6 cycloalkyl.

22. The compound of any one of claims 1-18, or a salt, solvate, or stereoisomer thereof, wherein R3cis optionally substituted phenyl.

23. The compound of any one of claims 1-3 or 6, or a salt, solvate, or stereoisomer thereof, wherein R3eis hydrogen.

24. The compound of any one of claims 1-22, or a salt, solvate, or stereoisomer thereof, wherein R3eis Ci-Cs alkoxy.

25. The compound of any one of claims 1-22, wherein R3eis -OH.

26. The compound of any one of claims 1-22, wherein R3eis -SH.

27. The compound of any one of claims 1-22, wherein R3eis Ci-Cs alkylthio.

28. The compound of any one of claims 1-22, wherein R3eis arylthio.

29. The compound of any one of claims 1-22, or a salt, solvate, or stereoisomer thereof, wherein R3eis C1-C9 alkyl.

30. The compound of any one of claims 1-22, or a salt, solvate, or stereoisomer thereof, wherein R3eis C3-C6 cycloalkyl.

31. The compound of any one of claims 1-22, or a salt, solvate, or stereoisomer thereof, wherein R3eis optionally substituted phenyl.

32. The compound of any one of claims 1-31, wherein R3fis hydrogen.

33. The compound of any one of claims 1-31, or a salt, solvate, or stereoisomer thereof, wherein R3fis C1-C9 alkyl.

34. The compound of any one of claims 1-31, or a salt, solvate, or stereoisomer thereof, wherein R3fis C3-C6 cycloalkyl.

35. The compound of any one of claims 1-31, or a salt, solvate, or stereoisomer thereof, wherein R3fis optionally substituted phenyl.

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

37. A composition comprising:(i) the compound of any one of claims 1-36; 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.

38. The composition of claim 37, wherein the composition comprises one or more elastomers.

39. The composition of claim 38, 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 elastomers.

40. The composition of any one of claims 37-39, wherein the one or more elastomers comprise natural rubber (NR).

41. The composition of claim 40, wherein the one or more elastomers comprises from about 5 wt / wt % to about 80 wt / wt % natural rubber (NR).

42. The composition of claim 40 or 41, wherein the natural rubber comprises rubber derived from an alternative rubber plant.

43. The composition of claim 42, wherein the alternative rubber plant is Parthenium argentatum (guayule) or Taraxacum kok-saghyz (Russian dandelion).

44. The composition of any one of claims 38-43, wherein the one or more elastomers comprise synthetic rubber.

45. The composition of claim 44, 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.

46. The composition of claim 45, 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.

47. The composition of claim 46, wherein the unsaturated rubber comprises styrene butadiene rubber (SBR).

48. The composition of claim 47, wherein the one or more elastomers comprise from about 5 wt / wt % to about 80 wt / wt % styrene butadiene rubber (SBR).

49. The composition of any one of claims 46-48, wherein the unsaturated rubber comprises polybutadiene rubber (BR).

50. The composition of claim 49, wherein the one or more elastomers comprise from about 5 wt / wt % to about 80 wt / wt % polybutadiene rubber (BR).

51. The composition of any one of claims 46-50, wherein the unsaturated rubber comprises butyl rubber (IIR).

52. The composition of claim 51, wherein the one or more elastomers comprise from about 1 wt / wt % to about 30 wt / wt % butyl rubber (IIR).

53. The composition of any one of claims 45-52, 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.

54. The composition of claims any one of claims 37-53, wherein the one or more elastomers further comprises recycled rubber.

55. The composition of any one of claims 37-54, wherein the composition comprises from about 0.1 phr to about 10 phr of the compound.

56. The composition of claim 55, wherein the composition comprises from about 0.5 phr to about 5 phr of the compound.

57. The compound of claim 56, wherein the composition comprises from about 1 phr to about 5 phr of the compound.

58. The composition of any one of claims 37-57, wherein the composition comprises one or more fillers.

59. The composition of claim 58, 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.

60. The composition of claims 58 or 59, wherein the composition comprises from about 30 phr to about 500 phr of one or more fillers.

61. The composition of any one of claims 58-60, 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.

62. The composition of claim 61, wherein the one or more fillers comprise silica.

63. The composition of claim 62, wherein the silica is derived from rice husks.

64. The composition of any one of claims 58-63, wherein the one or more fillers comprise carbon black.

65. The composition of any one of claims claim 37-64, wherein the composition comprises one or more rubber chemicals.

66. The composition of claim 65, wherein the composition comprises from about15 wt / wt % to about 85 wt / wt % of the compound and from about 15 wt / wt % to about 85 wt / wt % of one or more rubber chemicals.

67. The composition of claims 65 or 66, wherein the composition comprises from about 0.1 phr to about 30 phr of one or more rubber chemicals.

68. The composition of claim 67, wherein the composition comprises from about 1 phr to about 20 phr of one or more rubber chemicals.

69. The composition of any one of claims 64-68, 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.

70. The composition of claim 69, wherein the one or more rubber chemicals comprise one or more vulcanizing agents.

71. The composition of claim 70, wherein the one or more vulcanizing agents comprise sulfur, peroxide, resin, or a combination thereof.

72. The composition of claim 71, wherein the sulfur is octasulfur (Ss), cyclododecasulfur (S12), polymeric sulfur, or a combination thereof.

73. The composition of claim 71, 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.

74. The composition of claim 71, wherein the resin is a bonding resin.

75. The composition of claims 69-74, wherein the one or more rubber chemicals comprise one or more accelerators.

76. The composition of claim 75, 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.

77. The composition of claim 76, wherein the guanidine is diphenylguanidine (DPG).

78. The composition of claim 76, wherein the thiazole comprises 2-mercaptobenzothiazole (MBT), zinc 2-mercaptobenzothiazole (ZMBT), mercaptobenzothiazole disulfide (MBTS), / ' / - / ert-butyl-2 -benzothiazole sulfenimide (TBSI), or a combination thereof.

79. The composition of claim 76, wherein the sulfenamide comprises Af- / 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.

80. The composition of claim 76, 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.

81. The composition of claim 76, 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.

82. The composition of any one of claims 69-81, wherein the one or more rubber chemicals comprise one or more activators.

83. The composition of claim 82, wherein the one or more activators comprise a metal oxide, an acid, a metal complex, or a combination thereof.

84. The composition of claim 83, wherein the metal oxide comprises zinc oxide, magnesium oxide, lead oxide, or a combination thereof.

85. The composition of claim 83, wherein the acid comprises stearic acid, lauric acid, or a combination thereof.

86. The composition of claim 83, wherein the metal complex comprises zinc ethylhexanoate.

87. The composition of any one of claims 69-86, wherein the one or more rubber chemicals comprise one or more pre-vulcanization inhibitors.

88. The composition of claim 87, wherein the one or more pre-vulcanization inhibitors comprise 7V-(cyclohexylthio)phthalimide (CTP), benzoic anhydride, salicylic anhydride, phthalic anhydride, or a combination thereof.

89. The composition of any one of claims 37-88, wherein the composition comprises one or more plasticizers.

90. The composition of claim 89, wherein the composition comprises from about15 wt / wt % to about 85 wt / wt % of the compound and from about 15 wt / wt % to about 85 wt / wt % of one or more plasticizers.

91. The composition of claims 89 or 90, wherein the composition comprises from about 0.1 phr to about 30 phr of one or more plasticizers.

92. The composition of claim 91, wherein the composition comprises from about 1 phr to about 20 phr of one or more plasticizers.

93. The composition of any one of claims 89-92, 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.

94. The composition of claim 93, wherein the mineral oil is naphthenic oil, paraffinic oil, or aromatic oil.

95. The composition of claim 93, wherein the naturally derived oil is soybean oil, vegetable oil, or orange oil.

96. The composition of any one of claims 37-95, wherein the composition further comprises one or more additional anti degradants.

97. The composition of claim 96, wherein the composition comprises from about15 wt / wt % to about 85 wt / wt % of the compound and from about 15 wt / wt % to about 85 wt / wt % of one or more additional anti degradants.

98. The composition of claim 96 or 97, wherein the one or more additional anti degradants is present in an amount of from about 0.001 phr to about 10 phr.

99. The composition of claim 98, wherein the one or more additional anti degradants is present in an amount of from about 0.1 phr to about 5 phr.

100. The composition of claim 99, wherein the one or more additional anti degradants is present in an amount of from about 0.5 phr to about 5 phr.

101. The composition of claim 100, wherein the one or more additional anti degradants is present in an amount of from about 1 phr to about 5 phr.

102. The composition of any one of claims 96-101, wherein the one or more additional anti degradants is an antioxidant.

103. The composition of any one of claims 96-101, wherein the one or more additional anti degradants is an antiozonant.

104. The composition of any one of claims 96-103, wherein the one or more additional anti degradants is a paraphenylenediamine (PPD), a trimethyldihydroquinoline (TMQ), a phenolic, an alkylated diphenylamine (DPA), or a diphenylamine-ketone condensate.

105. The composition of claim 104, 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).

106. The composition of claim 105, wherein the PPD is 6PPD.

107. The composition of claim 104, wherein the TMQ is 2,2,4-trimethyl-l,2- dihydroquinoline or an oligomer or polymer thereof.

108. A composition comprising the compound of any one of claims 1-36 and one or more carriers.

109. A process for preparing the composition of claim 108, the process comprising admixing the compound and the one or more carriers.

110. A vulcanized elastomeric article comprising the compound of any one of claims 1-36.

111. A vulcanized elastomeric article prepared using the composition of any one of claims 37-108.

112. The vulcanized elastomeric article of claims 110 or 111, wherein the vulcanized elastomeric article is a tire.

113. The vulcanized elastomeric article of claim 112, 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.

114. The vulcanized elastomeric article of claims 110 or 111, wherein the vulcanized elastomeric article is a component of a tire.

115. The vulcanized elastomeric article of claim 114, wherein the component is a bead, a belt, a body ply, an inner liner, a sidewall, an undertread, or a tread.

116. The vulcanized elastomeric article of claims 110 or 111, 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.

117. A process for preparing a vulcanized elastomeric article, the process comprising:(a) forming the composition of any one of claims 38-107 into a formed shape; and(b) vulcanizing the formed shape to provide a vulcanized elastomeric article.

118. The process of claim 117, wherein the vulcanizing is performed at an average temperature of from about 120 °C to about 180 °C.

119. The process of claim 118, wherein the vulcanizing is performed at an average temperature of from about 140 °C to about 160 °C.

120. The process of any one of claims 117-119, wherein the vulcanized elastomeric article is a tire.

121. The process of claim 120, 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.

122. The process of any one of claims 117-121, wherein the vulcanized elastomeric article is a component of a tire.

123. The process of claim 122, wherein the component is a bead, a belt, a body ply, an inner liner, a sidewall, an undertread, or a tread.

124. The process of any one of claims 117-119, 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.

125. A lubricant composition comprising a lubricant and the compound of any one of claims 1-36.

126. A combustible fuel composition comprising a combustible fuel and the compound of any one of claims 1-36.

127. A fuel additive composition comprising a fuel additive and the compound of any one of claims 1-36.

128. A process for retreading tires, the process comprising:(a) applying the composition of any one of claims 37-108 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.

129. A kit comprising the composition of any one of claims 37-108 and instructions for using the composition in a vulcanizable elastomeric composition.

130. A kit comprising the composition of any one of claims 37-108 and instructions for using the composition to prepare a vulcanized elastomeric article.

131. The composition of any one of claims 37, 38, 40-58, 60-65, 67-89, 91-96, or 98- 107, wherein the composition comprises from about 0.1 wt / wt % to about 10 wt / wt % of the compound.

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