Quinoline imine anti-degradation agent compounds and uses thereof

Abstract

The present disclosure provides a compound represented by Formula (I) or (VIII): (I) (VIII), or a salt or solvate thereof, wherein R1, R2a, R2b, R2c, R3a, R3b, R3c, R3d, R8a, R8b, R9a, R9b, R9c, R9d, R10a, R10b, R10c, and R10d are as defined in the specification. The present disclosure also provides compositions, vulcanized elastomer articles, lubricant compositions, combustible fuel compositions, and fuel additive compositions comprising the compounds disclosed herein. The present disclosure also provides methods for making the compositions and vulcanized elastomeric articles described herein. The present disclosure also provides methods of retreading a tire using the compositions described herein. The present disclosure also provides kits comprising the compositions described herein.

Description

TECHNICAL FIELD

[0001] The present disclosure provides compounds having anti-degradation (e.g., anti- ozone, antioxidant, and / or anti-fatigue) properties that are useful additives for vulcanized rubber articles, compositions comprising elastomers, lubricants, fuels, and other compositions where such properties are desired or are themselves useful as compositions to impart such properties in compositions. BACKGROUND

[0003] Many materials such as plastics, elastomers, elastomeric products (tires, belts, hoses, bushings, mounts, isolators, etc.), lubricants, and petroleum products (such as hydraulic fluids, oils, fuels, and oil / fuel additives for automotive and aerospace applications) are susceptible to degradation upon prolonged exposure to light, heat, oxygen, ozone, repeated mechanical action, and the like. As a result, compounds and compositions that exhibit anti-degradation efficacy are well known in the art. For example, U.S. Patent No. 8,987,515 discloses an aromatic polyamine that is useful, inter alia, in lubricant compositions to inhibit oxidative degradation. U.S. Patent Application Publication No. 2014 / 0316163 discloses antioxidant macromolecules that are said to have improved solubility in many commercially available oils and lubricants.

[0004] Anti-degradation agents 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 anti-degradation agents must obviously have commercially acceptable efficacy, they must also exhibit that efficacy over the long period of time associated with the use of the article, particularly on the exposed surfaces of the article, as degradation caused by environmental factors such as light, oxygen, and ozone primarily occurs on those surfaces. Equally important as protecting the surface-exposed components, efficacy in protecting the embedded components of a composite from oxidative aging and repeated mechanical action is critical. Anti-degradation agents must achieve these results while not negatively impacting the efficacy of other additives or the desirable properties of the final article. Furthermore, anti-degradation agents that provide or improve mechanical fatigue life after use, oxidative aging, or exposure to ozone are highly valued as these will inherently improve the useful mechanical service life of the article. Thus, elastomeric articles that are subjected to repeated mechanical bending, stretching, or compression during use would greatly benefit from this discovery.

[0005] Articles, particularly tires, formed from general elastomers such as natural rubber are especially susceptible to degradation by oxygen and ozone. As described in U.S. Patent No. 2,905,654, the effects of oxygen degradation on rubber are different from the effects of ozone degradation on rubber; however, both effects are detrimental to the performance, appearance, and life of a tire. Fatigue and crack propagation are also issues of particular concern, especially in the steel belt edge region and the tire sidewall, which are subjected to great stress and tensile forces when the tire is flexed during inflation, partial inflation, uninflation, and throughout its useful life. U.S. Patent No. 8,833,417 describes an antioxidant system that is said to improve long-term fatigue and crack propagation resistance better than the known antioxidants discussed immediately below.

[0006] Materials having antidegradant efficacy for tire applications are well known in the art and are commercially available. For example, Ν,Ν'-disubstituted-p-phenylenediamines such as those sold under the trademark Santoflex® 6PPD by TM Chemical Corporation are generally favored by many tire manufacturers for this purpose. EP 3147321A1 discloses rubber compositions, tires, amine compounds, and anti-aging agents, in particular rubber compositions said to be suitable for use in the tread rubber or sidewall rubber of a tire.

[0007] Brief Description

[0008] The present disclosure provides compounds useful as antidegradants (e.g., antiozonants and / or antioxidants) and / or as additives in lubricants or combustible fuels, which are represented by any one of the following Formulas (I)-(X), collectively referred to herein as "the compounds of the present disclosure" or individually as "the compounds of the present disclosure."

[0009] The present disclosure also provides compositions comprising:

[0010] (i) the compounds of the present disclosure; and

[0011] (ii) one or more elastomers; or

[0012] (iii) one or more fillers; or

[0013] (iv) one or more rubber chemicals; or

[0014] (v) one or more plasticizers; or

[0015] (vi) one or more additional antidegradants; or

[0016] (vii) a combination of one or more elastomers, one or more fillers, one or more rubber chemicals, one or more plasticizers, and / or one or more additional antidegradants, collectively referred to herein as "the compositions of the present disclosure" or individually as "the compositions of the present disclosure."

[0017] The present disclosure also provides a composition of the present disclosure comprising a compound of the present disclosure and one or more fillers.

[0018] The present disclosure also provides a composition of the present disclosure comprising a compound of the present disclosure and one or more fillers.

[0019] The present disclosure also provides a composition of the present disclosure comprising a compound of the present disclosure and one or more rubber chemicals.

[0020] The present disclosure also provides a composition of the present disclosure comprising a compound of the present disclosure and one or more plasticizers.

[0021] The present disclosure also provides a composition of the present disclosure comprising a compound of the present disclosure and one or more additional antidegradants.

[0022] The present disclosure also provides a composition of the present disclosure comprising a compound of the present disclosure and one or more carriers.

[0023] The present disclosure also provides a method for making a composition comprising a compound of the present disclosure and one or more carriers, the method comprising mixing the compound and one or more carriers.

[0024] The present disclosure also provides a vulcanized elastomeric article comprising a compound of the present disclosure.

[0025] The present disclosure also provides a vehicle comprising a vulcanized elastomeric article, wherein the vulcanized elastomeric article comprises a compound of the present disclosure.

[0026] The present disclosure also provides a vulcanized elastomeric article made using a composition described herein (e.g., a composition of the present disclosure or a composition comprising a compound of the present disclosure and one or more carriers).

[0027] The present disclosure also provides a method for making a vulcanized elastomeric article described herein, the method comprising:

[0028] (a) forming a composition described herein into a shaped form; and

[0029] (b) vulcanizing the shaped form

[0030] to provide a vulcanized elastomeric article.

[0031] The present disclosure also provides a lubricant composition comprising a lubricant and a compound of the present disclosure.

[0032] The present disclosure also provides a combustible fuel composition comprising a combustible fuel and a compound of the present disclosure.

[0033] The present disclosure also provides a fuel additive composition comprising a fuel additive and a compound of the present disclosure.

[0034] The present disclosure also provides a method for retreading a tire, the method comprising:

[0035] (a) applying a composition described herein to a tire;

[0036] (b) disposing a pre-vulcanized tread around the tire;

[0037] (c) disposing a curing envelope around the tire; and

[0038] (d) curing the tire.

[0039] The present disclosure also provides a kit comprising a composition described herein and instructions for using the composition in a vulcanizable elastomer composition.

[0040] The present disclosure also provides a kit comprising a composition described herein and instructions for using the composition to make a vulcanized elastomer article.

[0041] Additional embodiments and advantages of the present 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 present disclosure. Embodiments and advantages of the present disclosure will be realized and attained by means of the elements and combinations specifically pointed out in the appended claims.

[0042] It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive of the application claimed. BRIEF DESCRIPTION OF DRAWINGS

[0043] Figure 1 is an NMR spectrum of compound 7.

[0044] Figure 2 is an LC chromatogram of compound 7. DETAILED DESCRIPTION

[0045] Without wishing to be bound by any particular theory, Applicants have found that the compounds of the present disclosure can form bonds with the elastomer during mixing or during the vulcanization process. The vulcanized articles thus obtained can contain both mobile and immobile (i.e., elastomer-bound) compounds with anti-degradant properties. It is desirable to find materials that can provide some balance between the mobile and immobile protective capabilities. For example, in a composite article, the mobile additives in the formulation migrate freely between the elements of the composite. At the same time, the allotrope of oxygen can react at the surface of the composite with the constituent materials of the composite, as in ozone, or anywhere in the composite, as in the case of diffusion-limited oxidation, including and especially within the interior components of the composite. Thus, materials designed to counteract the deleterious effects of oxygen should have two qualities. To some extent, they should migrate freely, especially to the surface of the composite, to prevent the deleterious effects of ozone, and, to some extent, a portion of the material should remain within the originally formulated components of the composite, thereby providing long-term protection against diffusion-limited reactions of oxygen. This is particularly desirable for interior components, as the concentration of mobile anti-degradants becomes insufficient within the interior components as surface reactions deplete them, thereby reducing the bearable protection of the interior components. If the anti-degradant additives form bonds with the elastomeric materials in the composite, it is ensured to some extent that they remain within that component throughout the useful life of the article. Thus, a single additive that can provide protection to the interior components of the composite while at the same time providing protection to the surface of the composite article is highly desirable. The ability to provide some balanced protection to the interior components while at the same time protecting the surface of the article or composite article is especially desirable in articles that are expected to have a long useful life, where multiple modes of degradation are possible, such as in the case of tires, hoses, belts, bushings, isolators that can be used in engine mounts, bridge bearings, and / or bearings for buildings.

[0046] In one embodiment, the compound of the present disclosure is a compound of Formula (I):

[0047]

[0048] or a salt, solvate, or stereoisomer thereof, wherein:

[0049] is a single or double bond;

[0050] R 1 is selected from the group consisting of optionally substituted C1-C 12 alkyl, -CHR 1a R 1b , C3-C6cycloalkyl, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;

[0051] R1a is selected from the group consisting of optionally substituted phenyl, C3-C6cycloalkyl and optionally substituted 5- or 6-membered heteroaryl;

[0052] R 1b is selected from the group consisting of hydrogen and C1-C9alkyl;

[0053] R 2a , R 2b and R 2c are independently selected from the group consisting of hydrogen, halogen, C1-C9alkyl, C1-C9haloalkyl, C3-C8cycloalkyl, C1-C8alkoxy, C1-C8alkylthio, -C(=O)OR 4 , -OC(=O)R 4 , -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NR 4 R 5 , -OH, -SH, -SC(=O)R 4 , -SC(=O)SR 4 , -SC(=O)NR 4 R 5 , -NR 4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 , 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio and arylamino; or

[0054] R 2a and R 2c together with the two carbon atoms to which they are attached form an optionally substituted C3-C6cycloalkyl, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted 4- to 6-membered aryl or optionally substituted 4- to 6-membered heteroaryl; and

[0055] R 2b is selected from the group consisting of hydrogen, halogen, C1-C9alkyl, C1-C9haloalkyl, optionally substituted C3-C8cycloalkyl, -OH, C1-C8alkoxy, -SH, C1-C8alkylthio, -C(=O)OR 4 , -OC(=O)R 4 , -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NHR 4 , -NR4 R 5 , -SC(=O)R 4 , -SC(=O)SR 4 , -SC(=O)NHR 4 , -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 , -NR 4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 , optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio, and arylamino;

[0056] R 3a is selected from the group consisting of hydrogen, halogen, C1-C9alkyl, optionally substituted phenyl, -C(=O)OR 4 , -C(=O)NR 4 R 5 , -C(=O)SR 4 , -CH2OR 4 , -CH2OC(=O)R 4 and

[0057] and

[0058] R 3b is selected from the group consisting of hydrogen, halogen, C1-C9alkyl, and optionally substituted phenyl; or

[0059] R 3a and R 3b together with the carbon atom to which they are attached form a C3-C 12 cycloalkyl;

[0060] R 3c is selected from the group consisting of hydrogen, halogen, C1-C9alkyl, optionally substituted phenyl, -C(=O)OR 4 , -C(=O)NR 4 R 5 , -C(=O)SR 4 , -CH2OR 4 , -CH2OC(=O)R 4 and

[0061] and

[0062] R 3dis selected from the group consisting of hydrogen, halogen, C1-C9alkyl, and optionally substituted phenyl; or

[0063] R 3c and R 3d together with the two carbon atoms to which they are attached form a C3-C 12 cycloalkyl;

[0064] R 4 is independently at each occurrence selected from the group consisting of hydrogen and C1-C9alkyl; and

[0065] R 5 is independently at each occurrence selected from the group consisting of hydrogen and C1-C9alkyl;

[0066] R 6a , R 6b , R 6c and R 6d is independently at each occurrence selected from the group consisting of hydrogen, C1-C 12 alkyl, and optionally substituted phenyl;

[0067] Z is independently at each occurrence selected from the group consisting of -O-, -S-, and -NR 7 ; and

[0068] R 7 is independently at each occurrence selected from the group consisting of hydrogen and C1-C6alkyl,

[0069] with the proviso that the compound of Formula (I) is not:

[0070]

[0071] In some embodiments, the compound of the disclosure is a compound of Formula (I), or a salt, solvate, or stereoisomer thereof, wherein:

[0072] is a single or double bond;

[0073] R 1 is selected from the group consisting of optionally substituted C1-C 12 alkyl, -CHR 1a R 1b , C3-C6cycloalkyl, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;

[0074] R 1a is selected from the group consisting of optionally substituted phenyl, C3-C6cycloalkyl, and optionally substituted 5- or 6-membered heteroaryl;

[0075] R 1b is selected from the group consisting of hydrogen and C1-C9alkyl;

[0076] R 2a , R 2b and R 2c are independently selected from the group consisting of hydrogen, halogen, C1-C9alkyl, C1-C9haloalkyl, C3-C8cycloalkyl, C1-C8alkoxy, C1-C8alkylthio, -C(=O)OR 4 , -OC(=O)R 4 , -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NHR 4 , -NR 4 R 5 , -OH, -SH, -SC(=O)R 4 , -SC(=O)SR 4 , -SC(=O)NHR 4 , -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 , -NR 4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 , 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio and arylamino; or

[0077] R 2a and R 2c together with the two carbon atoms to which they are attached form an optionally substituted C3-C6cycloalkyl, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted 4- to 6-membered aryl or optionally substituted 4- to 6-membered heteroaryl; and

[0078] R 2b is selected from the group consisting of hydrogen, halogen, C1-C9alkyl, C1-C9haloalkyl, optionally substituted C3-C8cycloalkyl, -OH, C1-C8alkoxy, -SH, C1-C8alkylthio, -C(=O)OR 4 , -OC(=O)R 4 , -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NHR 4 , -NR 4 R 5 , -SC(=O)R4 , -SC(=O)SR 4 , -SC(=O)NHR 4 , -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 , -NR 4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 , optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio, and arylamino;

[0079] R 3a and R 3b are independently selected from the group consisting of hydrogen, halogen, C1-C9alkyl, and optionally substituted phenyl; or

[0080] R 3a and R 3b together with the carbon atom to which they are attached form C3-C 12 cycloalkyl;

[0081] R 3c and R 3d are independently selected from the group consisting of hydrogen, halogen, C1-C9alkyl, and optionally substituted phenyl; or

[0082] R 3c and R 3d together with the two carbon atoms to which they are attached form C3-C 12 cycloalkyl;

[0083] R 4 is selected from the group consisting of hydrogen and C1-C9alkyl; and

[0084] R 5 is selected from the group consisting of hydrogen and C1-C9alkyl,

[0085] with the proviso that the compound of Formula (I) is not:

[0086]

[0087] In some embodiments, the compounds of the present disclosure are compounds of Formula (I), wherein R 3a , R 3b and R 3c are independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, pentyl, hexyl, heptyl, octyl, and nonyl.

[0088] In some embodiments, the compound of the present disclosure is a compound of Formula (I), wherein R 3a , R 3b , and R 3c are methyl.

[0089] In some embodiments, the compound of the present disclosure is a compound of Formula (I), wherein R 1 is optionally substituted phenyl.

[0090] In some embodiments, the compound of the present disclosure is a compound of Formula (I), wherein R 1 is substituted phenyl.

[0091] In some embodiments, the compound of the present disclosure is a compound of Formula (I), wherein R 1 is C1-C 12 alkyl.

[0092] In another embodiment, the compound of the present disclosure is a compound of Formula (I), wherein R 2a , R 2b , and R 2c are hydrogen.

[0093] In another embodiment, the compound of the present disclosure is a compound of Formula (I), wherein:

[0094] R 1 is selected from the group consisting of optionally substituted C1-C 12 alkyl, -CHR 1a R 1b , C3-C6cycloalkyl, 4- to 6-membered heterocyclyl, substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl; and

[0095] R 2a , R 2b , and R 2c are hydrogen.

[0096] In another embodiment, the compound of the present disclosure is a compound of Formula (I), wherein:

[0097] R 2a , R 2b , and R 2c are hydrogen;

[0098] R 3a is selected from the group consisting of hydrogen, halogen, C2-C9alkyl, and optionally substituted phenyl; and

[0099] R 3b is selected from the group consisting of hydrogen, halogen, C1-C9alkyl, and optionally substituted phenyl.

[0100] In another embodiment, the compound of the present disclosure is a compound of Formula (I), wherein:

[0101] R 2a , R 2b , and R 2c are hydrogen; and

[0102] R 3c is selected from the group consisting of hydrogen, halogen, C2-C9alkyl, and optionally substituted phenyl; and

[0103] R 3d is selected from the group consisting of hydrogen, halogen, C1-C9alkyl, and optionally substituted phenyl.

[0104] In another embodiment, the compound of the present disclosure is a compound of Formula (II):

[0105]

[0106] or a salt, solvate, or stereoisomer thereof, wherein

[0107] R 2a is selected from the group consisting of halogen, C1-C9alkyl, C1-C9haloalkyl, C3-C8cycloalkyl, C1-C8alkoxy, C1-C8alkylthio, C(=O)OR 4 , -OC(=O)R 4 , -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NHR 4 , -NR 4 R 5 , -OH, -SH, -SC(=O)R 4 , -SC(=O)SR 4 , -SC(=O)NHR 4 ,

[0108] -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 , -NR 4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 , 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio, and arylamino;

[0109] is a single or double bond; and

[0110] R 1 R 3a R 3b R 3c R 3d R 4 R 5 R

[0111] In some embodiments, the compound of the present disclosure is a compound of Formula (II), wherein R 2a is C1-C9alkyl.

[0112] In some embodiments, the compound of the present disclosure is a compound of Formula (II), wherein R 2a is methyl.

[0113] In another embodiment, the compound of the present disclosure is a compound of Formula (III):

[0114]

[0115] or a salt, solvate, or stereoisomer thereof, wherein

[0116] R 2b is selected from the group consisting of halogen, C1-C9alkyl, C1-C9haloalkyl, C3-C8cycloalkyl, C1-C8alkoxy, C1-C8alkylthio, C(=O)OR 4 , -OC(=O)R 4 , -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NHR 4 , -NR 4 R 5 , -OH, -SH, -SC(=O)R 4 , -SC(=O)SR 4 , -SC(=O)NHR 4 ,

[0117] -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 , -NR 4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 , 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio, and arylamino;

[0118] is a single or double bond; and

[0119] R 1 , R 3a , R 3b , R 3c , R 3d , R 4 , and R 5 are as defined in connection with formula (I).

[0120] In some embodiments, the compound of the present disclosure is a compound of formula (III), wherein R 2b is C1-C9 alkyl.

[0121] In some embodiments, the compound of the present disclosure is a compound of formula (III), wherein R 2b is methyl.

[0122] In another embodiment, the compound of the present disclosure is a compound of formula (IV):

[0123]

[0124] or a salt, solvate, or stereoisomer thereof, wherein:

[0125] R 2c is selected from the group consisting of halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C1-C8 alkylthio, -C(=O)OR 4 , -OC(=O)R 4 , -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NHR 4 , -NR 4 R 5 , -OH, -SH, -SC(=O)R 4 , -SC(=O)SR 4 , -SC(=O)NHR 4 ,

[0126] -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 , -NR 4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR5 , 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio, and arylamino;

[0127] is a single or double bond; and

[0128] R 1 , R 3a , R 3b , R 3c , R 3d , R 4 , and R 5 are as defined in connection with Formula (I).

[0129] In some embodiments, the compound of the present disclosure is a compound of Formula (IV), wherein R 2c is C1-C9 alkyl.

[0130] In some embodiments, the compound of the present disclosure is a compound of Formula (IV), wherein R 2c is methyl.

[0131] In another embodiment, the compound of the present disclosure is a compound of Formula (V):

[0132]

[0133] or a salt, solvate, or stereoisomer thereof, wherein:

[0134] R 2a and R 2b are independently selected from the group consisting of halogen, C 1- C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C1-C8 alkylthio, -C(=O)OR 4 ,

[0135] -OC(=O)R 4 , -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NHR 4 , -NR 4 R 5 , -OH, -SH, -SC(=O)R 4 ,

[0136] -SC(=O)SR 4 , -SC(=O)NHR 4 , -SC(=O)NR 4 R 5-NHC(=O)SR 4 -NR 4 C(=O)SR 5 ,

[0137] -NHC(=S)SR 4 -NR 4 C(=S)SR 5 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio, and arylamino;

[0138] is a single or double bond; and

[0139] R 1 R 3a R 3b R 3c R 3d R 4 R 5 are as defined in connection with formula (I).

[0140] In some embodiments, the compound of the present disclosure is a compound of formula (V), wherein R 2a R 2b are independently C1-C9alkyl.

[0141] In some embodiments, the compound of the present disclosure is a compound of formula (V), wherein R 2a R 2b are methyl.

[0142] In another embodiment, the compound of the present disclosure is a compound of formula (VI):

[0143]

[0144] or a salt, solvate, or stereoisomer thereof, wherein:

[0145] R 2a R 2c are independently selected from the group consisting of halogen, C1-C9alkyl, C1-C9haloalkyl, C3-C8cycloalkyl, C1-C8alkoxy, C1-C8alkylthio, -C(=O)OR 4 -OC(=O)R 4 -C(=O)NR 4 R 5 -NR 4 C(=O)R 5 -NHR 4 -NR 4 R 5 -OH, -SH,

[0146] -SC(=O)R 4 , -SC(=O)SR 4 , -SC(=O)NHR 4 , -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 ,

[0147] -NR 4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 , 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio, and arylamino;

[0148] is a single or double bond; and

[0149] R 1 , R 3a , R 3b , R 3c , R 3d , R 4 and R 5 are as defined in connection with Formula (I).

[0150] In some embodiments, the compound of the present disclosure is a compound of Formula (VI), wherein R 2a and R 2c are independently C1-C9alkyl.

[0151] In some embodiments, the compound of the present disclosure is a compound of Formula (VI), wherein R 2a and R 2c are methyl.

[0152] In another embodiment, the compound of the present disclosure is a compound of Formula (VII):

[0153]

[0154] or a salt, solvate, or stereoisomer thereof, wherein:

[0155] R 2b and R 2c are independently selected from the group consisting of halogen, C1-C9alkyl, C1-C9haloalkyl, C3-C8cycloalkyl, C1-C8alkoxy, C1-C8alkylthio, -C(=O)OR 4 , -OC(=O)R 4, -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NHR 4 , -NR 4 R 5 , -OH, -SH,

[0156] -SC(=O)R 4 , -SC(=O)SR 4 , -SC(=O)NHR 4 , -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 ,

[0157] -NR 4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 , 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio, and arylamino;

[0158] is a single or double bond; and

[0159] R 1 , R 3a , R 3b , R 3c , R 3d , R 4 and R 5 are as defined in connection with Formula (I).

[0160] In some embodiments, the compound of the present disclosure is a compound of Formula (VII), wherein R 2b and R 2c are independently C1-C9alkyl.

[0161] In some embodiments, the compound of the present disclosure is a compound of Formula (VII), wherein R 2b and R 2c are methyl.

[0162] In some embodiments, the compound of the present disclosure is a compound of Formula (I), wherein R 2a , R 2b and R 2c are independently selected from the group consisting of halogen, C1-C9alkyl, C1-C6alkoxy, and C1-C6alkylthio.

[0163] In some embodiments, the compound of the present disclosure is a compound of any of Formulae (II)-(VII), wherein R 2a , R 2b , and R 2c are independently selected from the group consisting of methyl, ethyl, methoxy, chloro, -SCH3, and -SCH2CH3.

[0164] In some embodiments, the compound of the present disclosure is a compound of any of Formulae (I)-(VII), wherein is a double bond.

[0165] In some embodiments, the compound of the present disclosure is a compound of any of Formulae (I)-(VII), wherein is a single bond.

[0166] In some embodiments, the compound of the present disclosure is a compound of any of Formulae (II)-(VII), wherein R 1 is optionally substituted phenyl.

[0167] In some embodiments, the compound of the present disclosure is a compound of any of Formulae (II)-(VII), wherein R 1 is C1-C 12 alkyl.

[0168] In some embodiments, the compound of the present disclosure is a compound of any of Formulae (II)-(VII), wherein R 1 is selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, pentyl, hexyl, heptyl, octyl, and nonyl.

[0169] In some embodiments, the compound of the present disclosure is a compound of any of Formulae (I)-(VII), wherein R 1 is -CHR 1a R 1b . In some embodiments, R 1a is selected from the group consisting of optionally substituted phenyl and optionally substituted 5- or 6-membered heteroaryl. In some embodiments, R 1a is phenyl or 2-furyl. In some embodiments, R 1b is hydrogen or methyl.

[0170] In some embodiments, the compound of the present disclosure is a compound of any of Formulae (II)-(VII), wherein R 3a , R 3b , and R 3c are independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, pentyl, hexyl, heptyl, octyl, and nonyl.

[0171] In some embodiments, the compound of the present disclosure is a compound of any one of formulae (II)-(VII), wherein R 3a , R 3b , and R 3c are methyl.

[0172] In some embodiments, the compound of the present disclosure is a compound of any one of formulae (I)-(VII), wherein R 3b is methyl; and R 3a and R 3c are C2-C9alkyl.

[0173] In some embodiments, the compound of the present disclosure is a compound of any one of formulae (I)-(VII), wherein R 3b is methyl; and R 3a and R 3c are ethyl.

[0174] In some embodiments, the compound of the present disclosure is a compound of any one of formulae (I)-(VII), wherein R 3a is -C(=O)OR 4 . In some embodiments, R 3a is -C(=O)OEt.

[0175] In some embodiments, the compound of the present disclosure is a compound of any one of formulae (I)-(VII), wherein R 3a is -C(=O)NR 4 R 5 .

[0176] In some embodiments, the compound of the present disclosure is a compound of any one of formulae (I)-(VII), wherein R 3a is -C(=O)SR 4 .

[0177] In some embodiments, the compound of the present disclosure is a compound of any one of formulae (I)-(VII), wherein R 3a is -CH2OR 4 .

[0178] In some embodiments, the compound of the present disclosure is a compound of any one of formulae (I)-(VII), wherein R 3a is -CH2OC(=O)R 4 .

[0179] In some embodiments, the compound of the present disclosure is a compound of any one of formulae (I)-(VII), wherein R 3a is

[0180]

[0181] In some embodiments, the compound of the present disclosure is a compound of any one of formulae (I)-(VII), wherein R 3c is -C(=O)OR 4 In some embodiments, R 3c is -C(=O)OEt.

[0182] In some embodiments, the compound of the present disclosure is a compound of any one of formulae (I)-(VII), wherein R 3c is -C(=O)NR 4 R 5 .

[0183] In some embodiments, the compound of the present disclosure is a compound of any one of formulae (I)-(VII), wherein R 3c is -C(=O)SR 4 .

[0184] In some embodiments, the compound of the present disclosure is a compound of any one of formulae (I)-(VII), wherein R 3c is -CH2OR 4 .

[0185] In some embodiments, the compound of the present disclosure is a compound of any one of formulae (I)-(VII), wherein R 3c is -CH2OC(=O)R 4 .

[0186] In some embodiments, the compound of the present disclosure is a compound of any one of formulae (I)-(VII), wherein R 3c is

[0187]

[0188] In some embodiments, the compound of the present disclosure is a compound of any one of formulae (I)-(VII), wherein Z is -O-. In some embodiments, Z is -S-. In some embodiments, Z is -NR 7 - In some embodiments, R 7 is hydrogen. In some embodiments, R 6a , R 6b , R 6c , and R 6d are hydrogen.

[0189] In some embodiments, the compound of the present disclosure is a compound of any one of formulae (I)-(VII), wherein each R4 is hydrogen or C1-C9alkyl.

[0190] In some embodiments, the compound of the present disclosure is a compound of any one of formulae (I)-(VII), wherein each R 4 is ethyl.

[0191] In some embodiments, the compound of the present disclosure is a compound of any one of formulae (I)-(VII), wherein each R 4 is hydrogen.

[0192] In some embodiments, the compound of the present disclosure is a compound of any one of formulae (I)-(VII), wherein R 3b is C1-C9alkyl.

[0193] In some embodiments, the compound of the present disclosure is a compound of any one of formulae (I)-(VII), wherein R 3b is methyl.

[0194] In some embodiments, the compound of the present disclosure is a compound of any one of formulae (I)-(VII), wherein R 3b is methyl; and R 3a and R 3c is -C(=O)OR 4 .

[0195] In some embodiments, the compound of the present disclosure is any one or more of the compounds of Table 1A, or a salt or solvate thereof.

[0196] Table 1A

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208] In another embodiment, the compound of the present disclosure is a compound of Formula (VIII):

[0209]

[0210] or a salt, solvate, or stereoisomer thereof, wherein:

[0211] each is independently a single or double bond;

[0212] R 8a and R 8b are independently selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C1-C8 alkylthio, -C(=O)OR 4 , -OC(=O)R 4 , -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NR 4 R 5 , -OH, -SH, -SC(=O)R 4 , -SC(=O)SR 4 , -SC(=O)NR 4 R 5 , -NR 4 C(=O)SR 5 , -NR 4 C(=S)SR 5 , 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio, and arylamino;

[0213] R 9a is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, optionally substituted phenyl, -C(=O)OR 4 , -C(=O)NR 4 R 5 , -C(=O)SR 4 , -CH2OR 4 , -CH2OC(=O)R 4 and

[0214] and

[0215] R 9b is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, and optionally substituted phenyl; or

[0216] R 9a and R 9b together with the carbon atom to which they are attached form a C3-C 12 cycloalkyl group;

[0217] R 9c is selected from the group consisting of hydrogen, halogen, C1-C9alkyl, optionally substituted phenyl, -C(=O)OR 4 , -C(=O)NR 4 R 5 , -C(=O)SR 4 , -CH2OR 4 , -CH2OC(=O)R 4 and

[0218] and

[0219] R 9d is selected from the group consisting of hydrogen, halogen, C1-C9alkyl and optionally substituted phenyl; or

[0220] R 9c and R 9d together with the two carbon atoms to which they are attached form a C3-C 12 cycloalkyl group;

[0221] R 10a is selected from the group consisting of hydrogen, halogen, C1-C9alkyl, optionally substituted phenyl, -C(=O)OR 4 , -C(=O)NR 4 R 5 , -C(=O)SR 4 , -CH2OR 4 , -CH2OC(=O)R 4 and

[0222] and

[0223] R 10b is selected from the group consisting of hydrogen, halogen, C1-C9alkyl and optionally substituted phenyl; or

[0224] R 10a and R 10b together with the carbon atom to which they are attached form a C3-C 12 cycloalkyl group;

[0225] R 10c is selected from the group consisting of hydrogen, halogen, C1-C9alkyl, optionally substituted phenyl, -C(=O)OR 4 , -C(=O)NR 4 R5 -C(=O)SR 4 -CH2OR 4 -CH2OC(=O)R 4 and

[0226] and

[0227] R 10d is selected from the group consisting of hydrogen, halogen, C1-C9alkyl, and optionally substituted phenyl; or

[0228] R 10c and R 10d together with the two carbon atoms to which they are attached form a C3-C 12 cycloalkyl;

[0229] Z is independently selected at each occurrence from the group consisting of -O-, -S-, and -NR 7 -;

[0230] R 4 is independently selected at each occurrence from the group consisting of hydrogen, C1-C9alkyl, C3-C6cycloalkyl, and optionally substituted phenyl; and

[0231] R 5 is independently selected at each occurrence from the group consisting of hydrogen, C1-C9alkyl, C3-C6cycloalkyl, and optionally substituted phenyl;

[0232] R 6a , R 6b , R 6c , and R 6d is independently selected at each occurrence from the group consisting of hydrogen, C1-C 12 alkyl, and optionally substituted phenyl; and

[0233] R 7 is independently selected at each occurrence from the group consisting of hydrogen and C1-C6alkyl.

[0234] In another embodiment, the compound of the disclosure is a compound of Formula (IX):

[0235]

[0236] or a salt, solvate, or stereoisomer thereof, wherein R 8a , R 8b , R 9a , R 9b , R 9c , R 9d , R 10a , R 10b , R 10c and R10d R is as defined in connection with Formula (VIII).

[0237] In another embodiment, the compound of the disclosure is a compound of Formula (X):

[0238]

[0239] or a salt, solvate, or stereoisomer thereof, wherein R 8a , R 8b , R 9a , R 9b , R 9c , R 9d , R 10a , R 10b , R 10c and R 10d are as defined in connection with Formula (VIII).

[0240] In some embodiments, the compound of the disclosure is a compound of any of Formulas (VIII)-(X), wherein R 8a and R 8b are hydrogen.

[0241] In some embodiments, the compound of the disclosure is a compound of any of Formulas (VIII)-(X), wherein R 8a and R 8b are methyl.

[0242] In some embodiments, the compound of the disclosure is a compound of any of Formulas (VIII)-(X), wherein R 9a , R 9b and R 9c are independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, pentyl, hexyl, heptyl, octyl, and nonyl.

[0243] In some embodiments, the compound of the disclosure is a compound of any of Formulas (VIII)-(X), wherein R 9a , R 9b and R 9c are methyl, ethyl, or isobutyl.

[0244] In some embodiments, the compound of the disclosure is a compound of any of Formulas (VIII)-(X), wherein R 9a and R 9c are methyl.

[0245] In some embodiments, the compound of the disclosure is a compound of any of Formulas (VIII)-(X), wherein R 9a and R9c ethyl.

[0246] In some embodiments, the compound of the disclosure is a compound of any one of Formulae (VIII)-(X), wherein R 9a and R 9c is isobutyl.

[0247] In some embodiments, the compound of the disclosure is a compound of any one of Formulae (VIII)-(X), wherein R 9b is methyl.

[0248] In some embodiments, the compound of the disclosure is a compound of any one of Formulae (VIII)-(X), wherein R 9a is -C(=O)OR 4 , -C(=O)NR 4 R 5 , -C(=O)SR 4 , -CH2OR 4 , -CH2OC(=O)R 4 or

[0249]

[0250] In some embodiments, the compound of the disclosure is a compound of any one of Formulae (VIII)-(X), wherein R 9a is -C(=O)OR 4 . In some embodiments, R 9a is -C(=O)OEt.

[0251] In some embodiments, the compound of the disclosure is a compound of any one of Formulae (VIII)-(X), wherein R 9a is -C(=O)NR 4 R 5 .

[0252] In some embodiments, the compound of the disclosure is a compound of any one of Formulae (VIII)-(X), wherein R 9a is -C(=O)SR 4 .

[0253] In some embodiments, the compound of the disclosure is a compound of any one of Formulae (VIII)-(X), wherein R 9a is -CH2OR 4 .

[0254] In some embodiments, the compound of the disclosure is a compound of any one of Formulae (VIII)-(X), wherein R 9a-CH2OC(=O)R 4 .

[0255] In some embodiments, the compound of the disclosure is a compound of any one of Formulae (VIII)-(X), wherein R 9a is

[0256]

[0257] In some embodiments, the compound of the disclosure is a compound of any one of Formulae (VIII)-(X), wherein R 9c is -C(=O)OR 4 In some embodiments, R 9c is -C(=O)OEt.

[0258] In some embodiments, the compound of the disclosure is a compound of any one of Formulae (VIII)-(X), wherein R 9c is -C(=O)NR 4 R 5 .

[0259] In some embodiments, the compound of the disclosure is a compound of any one of Formulae (VIII)-(X), wherein R 9c is -C(=O)SR 4 .

[0260] In some embodiments, the compound of the disclosure is a compound of any one of Formulae (VIII)-(X), wherein R 9c is -CH2OR 4 .

[0261] In some embodiments, the compound of the disclosure is a compound of any one of Formulae (VIII)-(X), wherein R 9c is -CH2OC(=O)R 4 .

[0262] In some embodiments, the compound of the disclosure is a compound of any one of Formulae (VIII)-(X), wherein R 9c is

[0263]

[0264] In some embodiments, the compound of the disclosure is a compound of any one of Formulae (VIII)-(X), wherein R 10a , R 10b , and R 10cis independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, pentyl, hexyl, heptyl, octyl, and nonyl.

[0265] In some embodiments, the compound of the disclosure is a compound of any one of Formulae (VIII)-(X), wherein R 10a , R 10b , and R 10c are methyl, ethyl, or isobutyl.

[0266] In some embodiments, the compound of the disclosure is a compound of any one of Formulae (VIII)-(X), wherein R 10a , and R 10c are methyl.

[0267] In some embodiments, the compound of the disclosure is a compound of any one of Formulae (VIII)-(X), wherein R 10a , and R 10c are ethyl.

[0268] In some embodiments, the compound of the disclosure is a compound of any one of Formulae (VIII)-(X), wherein R 10a , and R 10c are isobutyl.

[0269] In some embodiments, the compound of the disclosure is a compound of any one of Formulae (VIII)-(X), wherein R 10b is methyl.

[0270] In some embodiments, the compound of the disclosure is a compound of any one of Formulae (VIII)-(X), wherein R 10a is -C(=O)OR 4 , -C(=O)NR 4 R 5 , -C(=O)SR 4 , -CH2OR 4 , -CH2OC(=O)R 4 , or

[0271]

[0272] In some embodiments, the compound of the disclosure is a compound of any one of Formulae (VIII)-(X), wherein R 10a is -C(=O)OR 4 .In some embodiments, R 10a is -C(=O)OEt.

[0273] In some embodiments, the compound of the present disclosure is a compound of any one of Formulas (VIII)-(X), wherein R 10a is -C(=O)NR 4 R 5 .

[0274] In some embodiments, the compound of the present disclosure is a compound of any one of Formulas (VIII)-(X), wherein R 10a is -C(=O)SR 4 .

[0275] In some embodiments, the compound of the present disclosure is a compound of any one of Formulas (VIII)-(X), wherein R 10a is -CH2OR 4 .

[0276] In some embodiments, the compound of the present disclosure is a compound of any one of Formulas (VIII)-(X), wherein R 10a is -CH2OC(=O)R 4 .

[0277] In some embodiments, the compound of the present disclosure is a compound of any one of Formulas (VIII)-(X), wherein R 10a is

[0278]

[0279] In some embodiments, the compound of the present disclosure is a compound of any one of Formulas (VIII)-(X), wherein R 10c is -C(=O)OR 4 . In some embodiments, R 10c is -C(=O)OEt.

[0280] In some embodiments, the compound of the present disclosure is a compound of any one of Formulas (VIII)-(X), wherein R 10c is -C(=O)NR 4 R 5 .

[0281] In some embodiments, the compound of the present disclosure is a compound of any one of Formulas (VIII)-(X), wherein R 10c is -C(=O)SR 4 .

[0282] In some embodiments, the compound of the present disclosure is a compound of any one of Formulas (VIII)-(X), wherein R 10c is -CH2OR 4 .

[0283] In some embodiments, the compound of the disclosure is a compound of any one of Formulas (VIII)-(X), wherein R 10c is -CH2OC(=0)R 4 .

[0284] In some embodiments, the compound of the disclosure is a compound of any one of Formulas (VIII)-(X), wherein R 10c is

[0285]

[0286] In some embodiments, the compound of the disclosure is a compound of any one of Formulas (VIII)-(X), wherein Z is -0-. In some embodiments, Z is -S-. In some embodiments, Z is -NR 7 -. 7 is hydrogen. In some embodiments, R 6a , R 6b , R 6c , and R 6d are hydrogen.

[0287] In some embodiments, the compound of the disclosure is a compound of any one of Formulas (VIII)-(X), wherein each R 4 is hydrogen or Ci-C9alkyl.

[0288] In some embodiments, the compound of the disclosure is a compound of any one of Formulas (VIII)-(X), wherein each R 4 is ethyl.

[0289] In some embodiments, the compound of the disclosure is a compound of any one of Formulas (VIII)-(X), wherein each R 4 is hydrogen.

[0290] In some embodiments, the compound of the disclosure is a compound of any one of Formulas (VIII)-(X), wherein R 9a and R 10a are the same, e.g., R 9a and R 10a are each methyl, each ethyl, or each isobutyl.

[0291] In some embodiments, the compound of the disclosure is any one or more of the compounds of Table IB, or a salt or solvate thereof.

[0292] Table IB

[0293]

[0294]

[0295]

[0296]

[0297] The compounds disclosed herein can be used as anti-degradation agents (e.g., anti-ozone agents and / or antioxidants), as additives in lubricants, and as additives in combustible fuels.

[0298] The compounds disclosed herein can be prepared by dehydrogenation of the corresponding quinolinamine or bis(quinolinamine) as shown in Schemes 1 and 2. Dehydrogenation can be carried out using any method known in the art, i.e., treatment with an oxidant such as sodium hypochlorite, O2, H2O2, etc., in a solvent such as hexane, heptane, acetonitrile, etc., and optionally using a catalyst such as tetrabutylammonium bromide, etc.

[0299] Option 1

[0300]

[0301] Option 2

[0302]

[0303] definition

[0304] As used in this article, the term "alkyl" alone or as part of another group refers to a straight-chain or branched aliphatic hydrocarbon containing one to twelve carbon atoms, i.e., C1-C2. 12 Alkyl, or a specified number of carbon atoms, for example, C1-C3 alkyl, such as methyl, ethyl, propyl, or isopropyl; C1-C4 alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl, etc. 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 C1-C8 alkyl. In another embodiment, the alkyl is C1-C6 alkyl. In another embodiment, the alkyl is C1-C4 alkyl. In another embodiment, the alkyl is C1-C3 alkyl. Non-limiting exemplary C1-C 12 Alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, 3-pentyl, hexyl, heptyl, octyl, nonyl, and decyl.

[0305] The term "optionally substituted alkyl" as used herein alone or as part of another group refers to an alkyl group that is unsubstituted or substituted with one, two, or three substituents, wherein each substituent is independently nitro, cyano, hydroxyl, amino (e.g., -NH2, alkylamino, or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, cycloalkyl, or -C(=O)OR 1h wherein R 1h is C1-C6 alkyl.

[0306] The term "halo" or "halogen" as used herein alone or as part of another group refers to Cl, F, -Br, or -I.

[0307] The term "nitro" as used herein alone or as part of another group refers to NO2.

[0308] The term "cyano" as used herein alone or as part of another group refers to CN.

[0309] The term "hydroxyl" as used herein alone or as part of another group refers to OH.

[0310] The term "amino" as used alone or as part of another group refers to a group of the formula -NR 1f R 1g wherein R 1f and R 1g are independently hydrogen or alkyl.

[0311] In one embodiment, the amino group is -NH2.

[0312] In another embodiment, the amino group is an "alkylamino" group, i.e., an amino group wherein R 1f is C1-C6 alkyl and R 1g is hydrogen. In one embodiment, R 1f is C1-C4 alkyl. Non-limiting exemplary alkylamino groups include N(H)CH3 and N(H)CH2CH3.

[0313] In another embodiment, the amino group is a "dialkylamino" group, i.e., an amino group wherein R 1f and R 1g are each independently C 1-6 alkyl. In one embodiment, R 1f and R 1g are each independently C1-C4 alkyl. Non-limiting exemplary dialkylamino groups include -N(CH3)2 and -N(CH3)CH2CH(CH3)2.

[0314] The term "alkylcarbonyl" as used herein alone or as part of another group refers to a carbonyl group, i.e., -C(=0)-, substituted with an alkyl group. In one embodiment, the alkyl group is a C1-C4 alkyl group. A non-limiting exemplary alkylcarbonyl group is -COCH3.

[0315] The term "haloalkyl" as used herein alone or as part of another group refers to an alkyl group substituted with one or more fluorine, chlorine, bromine, and / or iodine atoms. In one embodiment, the alkyl group is substituted with one, two, or three fluorine and / or chlorine atoms. In another embodiment, the alkyl group is substituted with one, two, or three fluorine atoms. In another embodiment, the alkyl group is a C1-C6 alkyl group, and the resulting haloalkyl group is referred to as a "C1-C6 haloalkyl group." In another embodiment, the alkyl group is a C1-C4 alkyl group, and the resulting haloalkyl group is referred to as a "C1-C4 haloalkyl group." In another embodiment, the alkyl group is a C1 or C2 alkyl group. Non-limiting exemplary haloalkyl groups include fluoromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, 1,1 difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, 4,4,4-trifluorobutyl, and trichloromethyl groups.

[0316] The term "alkoxy" as used herein alone or as part of another group refers to an alkyl group attached to a terminal oxygen atom. In one embodiment, the alkyl group is a C1-C6 alkyl group, and the resulting alkoxy group is referred to as a "C1-C6 alkoxy group." In another embodiment, the alkyl group is a C1-C4 alkyl group, and thus the resulting alkoxy group is referred to as a "C1-C4 alkoxy group." Non-limiting exemplary alkoxy groups include methoxy, ethoxy, and t-butoxy.

[0317] The term "aryl" as used herein alone or as part of another group refers to an aromatic ring system having six to fourteen carbon atoms, i.e., C6-C 14 The term "aryl" as used herein alone or as part of another group refers to an aromatic ring system having six to fourteen carbon atoms, i.e., C6-C

[0318] The term "optionally substituted aryl" as used herein alone or as part of another group refers to an aryl group that is unsubstituted or substituted with one, two, three, four, or five substituents, each of which is independently a halo, nitro, cyano, hydroxyl, amino (e.g., -NH2, alkylamino, or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl, or cycloalkyl group, etc.

[0319] The term "aryloxy," as used herein alone or as part of another group, refers to an optionally substituted aryl group attached to an end oxygen atom. In one embodiment, the optionally substituted aryl group is an optionally substituted phenyl group. Non-limiting exemplary aryloxy groups include -O-phenyl.

[0320] The term "arylthio," as used herein alone or as part of another group, refers to an optionally substituted aryl group attached to an end sulfur atom. In one embodiment, the optionally substituted aryl group is an optionally substituted phenyl group. Non-limiting exemplary aryloxy groups include -S-phenyl.

[0321] The term "arylthio," as used herein alone or as part of another group, refers to an optionally substituted aryl group attached to an end sulfur atom. In one embodiment, the optionally substituted aryl group is an optionally substituted phenyl group. Non-limiting exemplary aryloxy groups include -S-phenyl.

[0322] The term "alkylthio," as used herein alone or as part of another group, refers to an alkyl group attached to an end sulfur atom. In one embodiment, the alkyl group is a C1-C6alkyl group, and the resulting alkylthio group is referred to as "C1-C6alkylthio." In one embodiment, the alkyl group is a C1-C4alkyl group, and the resulting alkylthio group is referred to as "C1-C4alkylthio." Non-limiting exemplary alkylthio groups include -SCH3and -SCH2CH3.

[0323] The term "cycloalkyl," as used herein alone or as part of another group, refers to a saturated and partially unsaturated (e.g., containing one or two double bonds) monocyclic, bicyclic, or tricyclic aliphatic hydrocarbon containing three to twelve carbon atoms, i.e., C3-C12cycloalkyl. In one embodiment, the cycloalkyl group is a monocyclic group, i.e., it has one ring. In another embodiment, the cycloalkyl group is a bicyclic group, i.e., it has two rings. In another embodiment, the cycloalkyl group is a tricyclic group, i.e., it has three rings. In another embodiment, the cycloalkyl group is a C3-C8cycloalkyl group. In another embodiment, the cycloalkyl group is a C3-C6cycloalkyl group. In another embodiment, the cycloalkyl group is a C5cycloalkyl group, i.e., a cyclopentyl group. In another embodiment, the cycloalkyl group is a C6cycloalkyl group, i.e., a cyclohexyl group. Non-limiting exemplary C3-C6cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. 12 Cycloalkyl, or the specified number of carbons, e.g., C3-C6cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. In one embodiment, the cycloalkyl group is bicyclic, i.e., it has two rings. In another embodiment, the cycloalkyl group is monocyclic, i.e., it has one ring. In another embodiment, the cycloalkyl group is a C3-C8cycloalkyl group. In another embodiment, the cycloalkyl group is a C3-C6cycloalkyl group. In another embodiment, the cycloalkyl group is a C5cycloalkyl group, i.e., a cyclopentyl group. In another embodiment, the cycloalkyl group is a C6cycloalkyl group, i.e., a cyclohexyl group. Non-limiting exemplary C3-C6cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. 12 Exemplary cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, norbornyl, decahydronaphthyl, adamantyl, cyclohexenyl, and spiro[3.3]heptane.

[0324] The term “optionally substituted phenyl” as used hereof, alone or as part of another group, refers to an unsubstituted phenyl or a phenyl substituted with one to five substituents, wherein the substituents are, for example, each independently a halogen, nitro, cyano, hydroxyl, amino (e.g., -NH2, alkylamino or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl or cycloalkyl.

[0325] As used herein, the term "heterocycle" alone or as part of another group refers to a saturated and partially unsaturated (e.g., containing one or two double bonds) monocyclic, bicyclic, or tricyclic group containing one, two, three, or four heteroatoms, comprising three to eighteen ring members, i.e., 3-membered to 18-membered heterocycles. Each heteroatom is independently oxygen, sulfur, or nitrogen. Each sulfur atom can be independently oxidized to give sulfoxide, i.e., S(=O); or sulfone, i.e., S(=O)2. The term heterocycle includes groups in which one or more CH2- groups are replaced by one or more -C(=O)- groups, including cyclic urea groups such as imidazolidinyl-2-one, cyclic amide groups such as pyrrolidine-2-one or piperidin-2-one, and cyclic carbamate groups such as oxazolidinyl-2-one. The term heterocyclic also includes groups having fused, optionally substituted aryl or optionally substituted heteroaryl groups, such as indoline, indoline-2-one, 2,3-dihydro-1H-pyrrolo[2,3-c]pyridine, 2,3,4,5-tetrahydro-1H-benzo[d]aza Or 1,3,4,5-tetrahydro-2H-benzo[d]aza -2-keto. In some embodiments, the heterocycle is a 6-membered ring containing one nitrogen atom. The heterocycle can fused with the rest of the molecule to form a bicyclic group, such as 1,2-dihydroquinoline or 1,2,3,4-tetrahydroquinoline.

[0326] The term “optionally substituted heterocycle” as used alone or as part of another group herein refers to an unsubstituted heterocyclic group or a heterocyclic group substituted with one to four substituents, wherein each substituent is independently a halogen, nitro, cyano, hydroxyl, amino (e.g., -NH2, alkylamino or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl or cycloalkyl.

[0327] The term "heteroaryl" as used herein alone or as part of another group refers to a monocyclic aromatic ring system having five to six ring members, i.e., 5- to 6-membered heteroaryl, containing one, two, three, four, or five heteroatoms. Each heteroatom is independently oxygen, sulfur, or nitrogen. In one embodiment, the heteroaryl group has three heteroatoms. In another embodiment, the heteroaryl group has two heteroatoms. In another embodiment, the heteroaryl group has one heteroatom. In another embodiment, the heteroaryl group has 5 ring atoms, for example, furanyl, i.e., a 5-membered heteroaryl group having four carbon atoms and one oxygen atom. In another embodiment, the heteroaryl group has 6 ring atoms, for example, pyridyl, which is a 6-membered heteroaryl group having five carbon atoms and one nitrogen atom. Non-limiting exemplary heteroaryl groups include thienyl, furanyl, pyranyl, 2H-pyrrolyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, thiazolyl, isothiazolyl, and isoxazolyl. In one embodiment, the heteroaryl group is selected from thienyl (e.g., thien-2-yl and thien-3-yl), furanyl (e.g., 2-furanyl and 3-furanyl), pyrrolyl (e.g., 1H-pyrrol-2-yl and 1H-pyrrol-3-yl), imidazolyl (e.g., 2H-imidazol-2-yl and 2H-imidazol-4-yl), pyrazolyl (e.g., 1H-pyrazol-3-yl, 1H-pyrazol-4-yl, and 1H-pyrazol-5-yl), pyridyl (e.g., pyrid-2-yl, pyrid-3-yl, and pyrid-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.

[0328] The term "optionally substituted heteroaryl" as used herein alone or as part of another group refers to a heteroaryl group that is unsubstituted or substituted with one to four substituents, wherein the substituents are independently halo, nitro, cyano, hydroxy, amino (e.g., -NH2, alkylamino, or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl, or cycloalkyl.

[0329] The term "stereoisomer" as used herein is a general term for all isomers of a molecule that have the same number and kind of atoms, but differ in the spatial arrangement of the atoms. It includes enantiomeric pairs of compounds, which are mirror images of one another and are not superimposable, and the diastereomeric pairs of compounds, which are not mirror images of one another and are not superimposable.

[0330] In some embodiments, the compounds of the present disclosure comprise a mixture of E and Z stereoisomers as exemplified by Compound Number 1 below:

[0331]

[0332] In some embodiments, the compounds of the present disclosure comprise a mixture of E and Z stereoisomers, wherein the E:Z ratio is 500: 1 to 1:500. In some embodiments, the E:Z ratio is 100: 1 to 1: 100. In some embodiments, the E:Z ratio is 10: 1 to 1: 10. In some embodiments, the E:Z ratio is 5: 1 to 1:5. In some embodiments, the E:Z ratio is 3: 1 to 1:3. In some embodiments, the E:Z ratio is 2: 1 to 1:2. In some embodiments, the E:Z ratio is about 10: 1, about 9: 1, about 8: 1, about 7: 1, about 6: 1, about 5: 1, about 4: 1, about 3: 1, or about 2: 1. In some embodiments, the E:Z ratio is about 1: 10, about 1:9, about 1:8, about 1:7, about 1:6, about 1:5, about 1:4, about 1:3, or about 1:2. In some embodiments, the E:Z ratio is about 1: 1.

[0333] In some embodiments, the compounds of the present disclosure comprise only the E stereoisomer, i.e., there is no detectable amount of the Z stereoisomer as measured by HPLC.

[0334] In some embodiments, the compounds of the present disclosure comprise only the Z stereoisomer, i.e., there is no detectable amount of the E stereoisomer as measured by HPLC.

[0335] The term "chiral center" or "asymmetric carbon atom" means a carbon atom to which four different groups are attached.

[0336] The terms "enantiomer" and "enantiomeric" mean a molecule that is not superimposable on its mirror image and thus has optical activity, wherein the enantiomer rotates the plane of polarized light in one direction, while its mirror image compound rotates the plane of polarized light in the opposite direction.

[0337] The term "racemic" means an equal mixture of enantiomers and the mixture is optically inactive.

[0338] The term "absolute configuration" means the spatial arrangement of atoms and its stereochemical description of a chiral molecular entity (or group), e.g., R or S.

[0339] The stereochemical terminology and conventions used in the specification are intended to be consistent with those described in Pure & Appl. Chem 68:2193 (1996), unless otherwise indicated.

[0340] The term "enantiomeric excess" or "ee" refers to a measure of how much of one enantiomer exists compared to the other. For a mixture of R and S enantiomers, the enantiomeric excess percentage is defined as |R-S|*100, where R and S are the respective molar or weight fractions of the enantiomers in the mixture, such that R+S = 1. From knowledge of the optical rotation of a chiral substance, the enantiomeric excess percentage is defined as ([a] obs / [a] max )*100, where [a] obs is the optical rotation of the enantiomeric mixture, [a] max is the optical rotation of the pure enantiomer. Enantiomeric excess can be determined using a variety of analytical techniques, including NMR spectroscopy, chiral column chromatography, or optical rotation.

[0341] In thin layer chromatography (TLC), the term R f represents the retention factor. R f is defined as the distance traveled by a single component divided by the total distance traveled by the eluent. Its value is always between zero and one.

[0342] Salts and solvates (e.g., hydrates) of the compounds of the disclosure can also be used in the methods disclosed herein.

[0343] The present disclosure encompasses the preparation and use of salts of the compounds of the present disclosure. Salts of the compounds of the present disclosure can be prepared during the final isolation and purification of the compounds. The salts can separately be prepared by reacting the compounds of the present disclosure with an acid having a suitable cation. Salts of the compounds of the present disclosure can be acid addition salts with an acceptable acid. Examples of acids that can be employed to provide salts include inorganic acids such as nitric, boric, hydrochloric, hydrobromic, sulfuric, and phosphoric acids, and organic acids such as oxalic, maleic, succinic, and citric acids. Non-limiting examples of salts of the compounds of the present disclosure include, but are not limited to, hydrochlorides, hydrobromides, hydroiodides, sulfates, bisulfates, 2-hydroxyethansulfonates, phosphates, hydrogenphosphates, acetates, adipates, alginates, aspartates, benzoates, bisulfates, butyrates, camphorates, camphorsulfonates, digluconates, glycerophosphates, hemisulfates, heptanoates, hexanoates, formates, succinates, fumarates, maleates, ascorbates, isethionates, salicylates, methanesulfonates, mesitylenesulfonates, naphthylenesulfonates, nicotinates, 2-naphthalenesulfonates, oxalates, palmoates, pectinates, persulfates, 3-phenylpropionates, picrates, pivalates, propionates, trichloroacetates, trifluoroacetates, phosphates, glutamates, bicarbonates, p-toluenesulfonates, undecanoates, lactates, citrates, tartarates, gluconates, methanesulfonates, ethanedisulfonates, benzenesulfonates, and p-toluenesulfonates. Additionally, amino groups present in the compounds of the present disclosure can be quaternized with such agents as methyl, ethyl, propyl, and butyl chlorides, bromides, and iodides; dimethyl, diethyl, dibutyl, and diamyl sulfates; decyl, lauryl, myristyl, and stearyl chlorides, bromides, and iodides; and benzyl and phenethyl bromides. In view of the above, any reference herein to a compound of the present disclosure is intended to include a compound of the present disclosure and salts, hydrates, or solvates thereof.

[0344] The present disclosure encompasses the preparation and use of solvates of the compounds of the present disclosure. As used herein, the term “solvate” is a combination, physical association, and / or solvation of a compound of the present disclosure with a solvent molecule, such as a disolvate, monosolvate, or hemisolvate, where the solvent molecule is about 2:1, about 1:1, or about 1:2, respectively, in ratio to the compound of the present disclosure. Such physical associations involve varying degrees of ionic and covalent bonding, including hydrogen bonding. In certain instances, solvates can be isolated, such as when one or more solvent molecules are incorporated into the crystal lattice of a crystalline solid. Thus, “solvate” includes solution-phase and isolatable solvates. The compounds of the present disclosure can exist in solvated forms with solvents such as water, methanol, and ethanol, and the present disclosure is intended to include both solvated and unsolvated forms of the compounds of the present disclosure.

[0345] One solvate is a hydrate. The term "hydrate" refers to a specific subgroup of solvates in which the solvent molecule is water. The 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 a solvate of fluconazole with ethyl acetate and water. Similar preparations of solvates, semi-solvates, hydrates, etc., are described by van Tonder et al., AAPS Pharm. Sci. Tech., 5(1):Article 12 (2004) and ALBingham et al., Chem. Commun. 603-604 (2001). A typical, non-limiting process for preparing a solvate would involve dissolving the compound of this disclosure in a desired solvent (organic solvent, water, or mixtures thereof) at a temperature above 20°C to about 25°C, then cooling the solution at a rate sufficient to form crystals, and separating the crystals by known methods (e.g., filtration). Analytical techniques such as infrared spectroscopy can be used to confirm the presence of solvent in solvate crystals.

[0346] Unless otherwise stated, in the context of describing this disclosure (especially in the context of the claims), the use of the terms “a,” “an,” “the,” and similar references should be interpreted as covering both the singular and plural. Unless otherwise stated herein, references to ranges of values ​​herein are intended only to serve as a shorthand method for individually referring to each individual value within that range, and each individual value is incorporated into the specification as if it were individually referenced herein. Unless otherwise stated, the use of any and all instances or exemplary language (e.g., “such as”) provided herein is intended to better illustrate this disclosure and not to limit the scope of this disclosure. The language in this specification should not be construed as indicating that any unclaimed element is necessary for practicing this disclosure.

[0347] Furthermore, the term “and / or” as used herein should be considered as a specific disclosure of each of the two specified features or components, with or without the other. Thus, the term “and / or” as used in phrases such as “A and / or B” herein is intended to include “A and B”, “A or B”, “A” (alone), and “B” (alone). Similarly, the term “and / or” as used in phrases such as “A, B, and / or C” is intended to include each of the following: 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).

[0348] It should be understood that whenever the language “contains” is used in this document to describe an aspect, other similar aspects described by “consisting of” and / or “substantially consisting of” are also provided.

[0349] As used herein, the term "weight / weight %" 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 total mass of all components in the composition or blend multiplied by 100. For example, in a composition comprising 1 kg of a compound of the disclosure, 1 kg of natural rubber, and 2 kg of synthetic rubber, the weight / weight % of the compound is 25 weight / weight % (1 kg / 4 kg = 0.25 x 100 = 25 weight / weight %). In a composition comprising 1 kg of a compound of the disclosure and 1 kg of carbon black, the weight / weight % of the compound is 50 weight / weight % (1 kg / 2 kg = 0.50 x 100 = 50 weight / weight %). In a composition comprising 1 kg of a compound of the disclosure, 1 kg of natural rubber, 2 kg of synthetic rubber, and 1 kg of carbon black, the weight / weight % of the compound is 20 weight / weight % (1 kg / 5 kg = 0.20 x 100 = 20 weight / weight %). In a blend of one or more elastomers comprising 20 kg of natural rubber and 30 kg of synthetic rubber, the weight / weight % of the natural rubber is 40 weight / weight % (20 kg / 50 kg = 0.40 x 100 = 40 weight / weight %).

[0350] As used herein, the term “masterbatch” refers to a composition comprising at least one elastomer and a compound of the present disclosure. In some embodiments, the masterbatch comprises from about 5 weight / weight % to about 95 weight / weight % of at least one elastomer and from about 5 weight / weight % to about 95 weight / weight % of a compound of the present disclosure. In some embodiments, the masterbatch comprises about 5 weight / weight %, about 10 weight / weight %, about 15 weight / weight %, about 20 weight / weight %, about 25 weight / weight %, about 30 weight / weight %, about 35 weight / weight %, about 40 weight / weight %, about 45 weight / weight %, about 50 weight / weight %, about 55 weight / weight %, about 60 weight / weight %, about 65 weight / weight %, about 70 weight / weight %, about 75 weight / weight %, about 80 weight / weight %, about 85 weight / weight %, about 90 weight / weight %, or about 95 weight / weight % of a compound of the present disclosure. In some embodiments, the masterbatch comprises about 5 weight / weight %, about 10 weight / weight %, about 15 weight / weight %, about 20 weight / weight %, about 25 weight / weight %, about 30 weight / weight %, about 35 weight / weight %, about 40 weight / weight %, about 45 weight / weight %, about 50 weight / weight %, about 55 weight / weight %, about 60 weight / weight %, about 65 weight / weight %, about 70 weight / weight %, about 75 weight / weight %, about 80 weight / weight %, about 85 weight / weight %, about 90 weight / weight %, or about 95 weight / weight % of at least one elastomer.

[0351] As used herein, the term "premix" refers to a composition comprising a compound of the present 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 weight / weight % to about 95 weight / weight % of a compound of the present disclosure and from about 5 weight / weight % to about 95 weight / weight % of 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 comprises about 5 weight / weight %, about 10 weight / weight %, about 15 weight / weight %, about 20 weight / weight %, about 25 weight / weight %, about 30 weight / weight %, about 35 weight / weight %, about 40 weight / weight %, about 45 weight / weight %, about 50 weight / weight %, about 55 weight / weight %, about 60 weight / weight %, about 65 weight / weight %, about 70 weight / weight %, about 75 weight / weight %, about 80 weight / weight %, about 85 weight / weight %, about 90 weight / weight %, or about 95 weight / weight % of a compound of the present disclosure. In some embodiments, the premix comprises about 5 weight / weight %, about 10 weight / weight %, about 15 weight / weight %, about 20 weight / weight %, about 25 weight / weight %, about 30 weight / weight %, about 35 weight / weight %, about 40 weight / weight %, about 45 weight / weight %, about 50 weight / weight %, about 55 weight / weight %, about 60 weight / weight %, about 65 weight / weight %, about 70 weight / weight %, about 75 weight / weight %, about 80 weight / weight %, about 85 weight / weight %, about 90 weight / weight %, or about 95 weight / weight % of at least one additional component, e.g., a filler, a rubber chemical, a plasticizer, an additional anti-degradant, or a combination thereof.

[0352] As used herein, the term "one or more" is intended to mean that at least one component of the relevant class of components is present, such as one or more elastomers, or at least one component of the disclosed list, such as one or more fluorine, chlorine, bromine, and / or iodine atoms, and in some embodiments, more than one component is present. In some embodiments, one or more means 1 to 50. In some embodiments, one or more means 1 to 40. In some embodiments, one or more means 1 to 30. In some embodiments, one or more means 1 to 20. In some embodiments, one or more means 1 to 10. In some embodiments, one or more means 1 to 5. In some embodiments, one or more means 1 to 3. In some embodiments, one or more means 1 or 2. In some embodiments, one or more means 1.

[0353] Compositions and methods of use

[0354] In another embodiment, the present disclosure provides a composition comprising:

[0355] (i) a compound of the present disclosure; and

[0356] (ii) one or more elastomers; or

[0357] (iii) one or more fillers; or

[0358] (iv) one or more rubber chemicals; or

[0359] (v) one or more plasticizers; or

[0360] (vi) one or more additional antidegradants; or

[0361] (vii) a combination of one or more elastomers, one or more fillers, one or more rubber chemicals, one or more plasticizers, and / or one or more additional antidegradants.

[0362] In some embodiments, the composition comprises about 0.1% to about 10% of a compound of the present disclosure by weight / weight %, e.g., about 0.1% to about 0.5%, about 0.1% to about 1%, about 0.1% to about 1.5%, about 0.1% to about 2%, about 0.1% to about 2.5%, about 0.1% to about 3%, about 0.1% to about 3.5%, about 0.1% to about 4%, about 0.1% to about 4.5%, about 0.1% to about 5%, about 0.1% to about 6%, about 0.1% to about 7%, about 0.1% to about 8%, about 0.1% to about 9%, about 0.1% to about 10%, about 0.5% to about 1%, about 0.5% to about 1.5%, about 0.5% to about 2%, about 0.5% to about 2.5%, about 0.5% to about 3%, about 0.5% to about 3.5%, about 0.5% to about 4%, about 0.5% to about 4.5%, about 0.5% to about 5%, about 0.5% to about 6%, about 0.5% to about 7%, about 0.5% to about 8%, about 0.5% to about 9%, about 0.5% to about 10%, about 1% to about 2%, about 1% to about 2.5%, about 1% to about 3%, about 1% to about 3.5%, about 1% to about 4%, about 1% to about 4.5%, about 1% to about 5%, about 1% to about 6%, about 1% to about 7%, about 1% to about 8%, about 1% to about 9%, about 1% to about 10%, about 1.5% to about 2%, about 1.5% to about 2.5%, about 1.5% to about 3%, about 1.5% to about 3.5%, about 1.5% to about 4%, about 1.5% to about 4.5%, about 1.5% to about 5%, about 1.5% to about 6%, about 1.5% to about 7%, about 1.5% to about 8%, about 1.5% to about 9%, about 1.5% to about 10%, about 2% to about 3%, about 2% to about 3.5%, about 2% to about 4%, about 2% to about 4.5%, about 2% to about 5%, about 2% to about 6%, about 2% to about 7%, about 2% to about 8%, about 2% to about 9%, about 2% to about 10%, about 2.5% to about 3%, about 2.5% to about 3.5%, about 2.5% to about 4%, about 2.5% to about 4.5%, about 2.5% to about 5%, about 2.5% to about 6%, about 2.5% to about 7%, about 2.5% to about 8%, about 2.5% to about 9%, about 2.5% to about 10%, about 3% to about 4%, about 3% to about 4.5%, about 3% to about 5%, about 3% to about 6%, about 3% to about 7%, about 3% to about 8%, about 3% to about 9%, about 3% to about 10%, about 3.5% to about 4%, about 3.5% to about 4.5%, about 3.5% to about 5%, about 3.5% to about 6%, about 3.5% to about 7%, about 3.5% to about 8%, about 3.5% to about 9%, about 3.5% to about 10%, about 4% to about 5%, about 4% to about 6%, about 4% to about 7%, about 4% to about 8%, about 4% to about 9%, about 4% to about 10%, about 4.5% to about 5%, about 4.5% to about 6%, about 4.5% to about 7%, about 4.5% to about 8%, about 4.5% to about 9%, about 4.5% to about 10%, about 5% to about 6%, about 5% to about 7%, about 5% to about 8%, about 5% to about 9%, about 5% to about 10%, about 6% to about 7%, about 6% to about 8%, about 6% to about 9%, about 6% to about 10%, about 7% to about 8%, about 7% to about 9%, about 7% to about 10%, about 8% to about 9%, about 8% to about 10%, or about 9% to about 10% by weight / weight %.5 wt / wt% to about 5 wt / wt%, about 1.5 wt / wt% to about 6 wt / wt%, about 1.5 wt / wt% to about 7 wt / wt%, about 1.5 wt / wt% to about 8 wt / wt%, about 1.5 wt / wt% to about 9 wt / wt%, about 1.5 wt / wt% to about 10 wt / wt%, about 2 wt / wt% to about 2.5 wt / wt%, about 2 wt / wt% to about 3 wt / wt%, about 2 wt / wt% to about 3.5 wt / wt%, about 2 wt / wt% to about 4 wt / wt%, about 2 wt / wt% to about 4.5 wt / wt%, about 2 wt / wt% to about 5 wt / wt%, about 2 wt / wt% to about 6 wt / wt%, about 2 wt / wt% to about 7 wt / wt%, about 2 wt / wt% to about 8 wt / wt%, about 2 wt / wt% to about 9 wt / wt%, about 2 wt / wt% to about 10 wt / wt%, about 2.5 wt / wt% to about 3 wt / wt%, about 2.5 wt / wt% to about 3.5 wt / wt%, about 2.5 wt / wt% to about 4 wt / wt%, about 2.5 wt / wt% to about 4.5 wt / wt%, about 2.5 wt / wt% to about 5 wt / wt%, about 2.5 wt / wt% to about 6 wt / wt%, about 2.5 wt / wt% to about 7 wt / wt%, about 2.5 wt / wt% to about 8 wt / wt%, about 2.5 wt / wt% to about 9 wt / wt%, about 2.5 wt / wt% to about 10 wt / wt%, about 3 wt / wt% to about 4 wt / wt%, about 3 wt / wt% to about 4.5 wt / wt%, about 3 wt / wt% to about 5 wt / wt%, about 3 wt / wt% to about 6 wt / wt%, about 3 wt / wt% to about 7 wt / wt%, about 3 wt / wt% to about 8 wt / wt%, about 3 wt / wt% to about 9 wt / wt%, about 3 wt / wt% to about 10 wt / wt%, about 3.5 wt / wt% to about 4 wt / wt%, about 3.5 wt / wt% to about 4.5 wt / wt%, about 3.5 wt / wt% to about 5 wt / wt%, about 3.5 wt / wt% to about 6 wt / wt%, about 3.5 wt / wt% to about 7 wt / wt%, about 3.5 wt / wt% to about 8 wt / wt%, about 3.5 wt / wt% to about 9 wt / wt%, about 3.5 wt / wt% to about 10 wt / wt%, about 4 wt / wt% to about 4.5 wt / wt%, about 4 wt / wt% to about 5 wt / wt%, about 4 wt / wt% to about 6 wt / wt%, about 4 wt / wt% to about 7 wt / wt%, about 4 wt / wt% to about 8 wt / wt%, about 4 wt / wt% to about 9 wt / wt%, about 4 wt / wt% to about 10 wt / wt%, about 4.5 wt / wt% to about 5 wt / wt%, about 4.5 wt / wt% to about 6 wt / wt%, about 4.5 wt / wt% to about 7 wt / wt%, about 4.5 wt / wt% to about 8 wt / wt%, about 4.5 wt / wt% to about 9 wt / wt%, about 4.5 wt / wt% to about 10 wt / wt%, about 5 wt / wt% to about 6 wt / wt%, about 5 wt / wt% to about 7 wt / wt%, about 5 wt / wt% to about 8 wt / wt%, about 5 wt / wt% to about 9 wt / wt%, about 5 wt / wt% to about 10 wt / wt%, about 6 wt / wt% to about 7 wt / wt%, about 6 wt / wt% to about 8 wt / wt%, about 6 wt / wt% to about 9 wt / wt%, about 6 wt / wt% to about 10 wt / wt%, about 7 wt / wt% to about 8 wt / wt%, about 7 wt / wt% to about 9 wt / wt%, about 7 wt / wt% to about 10 wt / wt%, about 8 wt / wt% to about 9 wt / wt%, about 8 wt / wt% to about 10 wt / wt%, and about 9 wt / wt% to about 10 wt / wt%.5% to about 6% by weight, about 4.5% to about 7% by weight, about 4.5% to about 8% by weight, about 4.5% to about 9% by weight, about 4.5% to about 10% by weight, about 5% to about 6% by weight, about 5% to about 7% by weight, about 5% to about 8% by weight, about 5% to about 9% by weight, about 5% to about 10% by weight, about 6% to about 7% by weight, about 6% to about 8% by weight, about 6% to about 9% by weight, about 6% to about 10% by weight, about 7% to about 8% by weight, about 7% to about 9% by weight, about 8% to about 10% by weight, about 8% to about 9% by weight, about 8% to about 10% by weight, or about 9% to about 10% by weight of a compound of the disclosure.

[0363] In some embodiments, the compositions of the present disclosure comprise about 15% to about 85% of a compound of the present disclosure by weight / weight. In some embodiments, the compositions comprise about 1% to about 5%, about 1% to about 15%, about 1% to about 25%, about 1% to about 35%, about 1% to about 45%, about 1% to about 55%, about 1% to about 65%, about 1% to about 75%, about 1% to about 85%, about 1% to about 95%, about 5% to about 15%, about 5% to about 25%, about 5% to about 35%, about 5% to about 45%, about 5% to about 55%, about 5% to about 65%, about 5% to about 75%, about 5% to about 85%, about 5% to about 95%, about 15% to about 25%, about 15% to about 35%, about 15% to about 45%, about 15% to about 55%, about 15% to about 65%, about 15% to about 75%, about 15% to about 95%, about 25% to about 35%, about 25% to about 45%, about 25% to about 55%, about 25% to about 65%, about 25% to about 75%, about 25% to about 85%, about 25% to about 95%, about 35% to about 45%, about 35% to about 55%, about 35% to about 65%, about 35% to about 75%, about 35% to about 85%, about 35% to about 95%, about 45% to about 55%, about 45% to about 65%, about 45% to about 75%, about 45% to about 85%, about 45% to about 95%, about 55% to about 65%, about 55% to about 75%, about 55% to about 85%, about 55% to about 95%, about 65% to about 75%, about 65% to about 85%, about 65% to about 95%, about 75% to about 85%, about 75% to about 95%, or about 85% to about 95% of a compound of the present disclosure by weight / weight.about 65% to about 75% by weight / weight, about 65% to about 85% by weight / weight, about 65% to about 95% by weight / weight, about 75% to about 85% by weight / weight, about 75% to about 95% by weight / weight, or about 85% to about 95% by weight / weight of a compound of the disclosure.

[0364] In some embodiments, the composition of the disclosure comprises about 50% by weight / weight of a compound of the disclosure. In some embodiments, the composition comprises about 1% by weight / weight, about 5% by weight / weight, about 10% by weight / weight, about 15% by weight / weight, about 20% by weight / weight, about 25% by weight / weight, about 30% by weight / weight, about 35% by weight / weight, about 40% by weight / weight, about 45% by weight / weight, about 55% by weight / weight, about 60% by weight / weight, about 65% by weight / weight, about 70% by weight / weight, about 75% by weight / weight, about 80% by weight / weight, about 85% by weight / weight, about 90% by weight / weight, or about 95% by weight / weight of a compound of the disclosure.

[0365] In another embodiment, the composition of the disclosure comprises a compound of the disclosure and one or more elastomers.

[0366] As used herein, the term "elastomer" is a polymer that has viscoelasticity (i.e., has both viscosity and elasticity), which generally has low intermolecular forces, low Young's modulus, and high failure strain. Elastomers can generally be crosslinked by heat in the presence of one or more crosslinking agents, a process known as curing or vulcanization. Rubber is a type of elastomer. Non-limiting types of rubber include natural rubber (NR), synthetic rubber, and blends thereof. As used herein, the term "natural rubber" refers to a naturally occurring elastomer that can be obtained from a rubber tree. Non-limiting types of synthetic rubber include unsaturated rubber, saturated rubber, rubber having fluorine and fluoroalkyl or fluoroalkoxy substituent groups on the polymer chain (FKM), silicone rubber (Q), and blends thereof. Non-limiting examples of unsaturated rubber include polyisoprene rubber (IR), butyl rubber (IIR), polybutadiene rubber (BR), styrene-isoprene-butadiene rubber (SIBR), styrene butadiene rubber (SBR), nitrile rubber (NBR), chloroprene rubber (CR), ethylene propylene terpolymer rubber (EPDM), and blends thereof. These unsaturated rubbers undergo cyclization and crosslinking reactions, which cause the aged part to become hard. As oxidation occurs, these vulcanized rubbers become hard and eventually turn into a brittle product. Partial oxidation when used in applications such as vehicle tire sidewalls, for example, can result in a loss of performance. Saturated rubbers are rubbers that do not contain C=C unsaturation and include, but are not limited to, acrylic rubber (ACM), chlorinated polyethylene (CM), chlorosulfonated polyethylene (CSM), poly(chloromethyl)oxirane (CO), ethylene-ethyl acrylate copolymer (EAM), epichlorohydrin rubber (ECO), ethylene propylene rubber (EPM), ethylene vinyl acetate copolymer (EVM), rubber having fluorine and fluoroalkyl or fluoroalkoxy substituent groups on the polymer chain (FKM), silicone rubber (Q), and blends thereof.

[0367] In some embodiments, the natural rubber includes rubber derived from alternative rubber plants. As used herein, the term "natural rubber includes rubber derived from alternative rubber plants" refers to a naturally occurring elastomer that can be obtained from a "non-rubber tree" source. In some embodiments, the alternative rubber plant is Parthenium argentatum (guayule) or Taraxacum kok-saghyz (Russian dandelion).

[0368] In some embodiments, the one or more elastomers further comprise reclaimed rubber. As used herein, the term "reclaimed rubber" refers to an elastomer that is recovered from scrap material such as scrap tires.

[0369] In some embodiments, the composition of the present disclosure comprises about 15 weight / weight % to about 100 weight / weight % of one or more elastomers. In some embodiments, the composition comprises about 1 weight / weight % to about 5 weight / weight %, about 1 weight / weight % to about 15 weight / weight %, about 1 weight / weight % to about 25 weight / weight %, about 1 weight / weight % to about 35 weight / weight %, about 1 weight / weight % to about 45 weight / weight %, about 1 weight / weight % to about 55 weight / weight %, about 1 weight / weight % to about 65 weight / weight %, about 1 weight / weight % to about 75 weight / weight %, about 1 weight / weight % to about 85 weight / weight %, about 1 weight / weight % to about 95 weight / weight %, about 1 weight / weight % to about 100 weight / weight %, about 5 weight / weight % to about 15 weight / weight %, about 5 weight / weight % to about 25 weight / weight %, about 5 weight / weight % to about 35 weight / weight %, about 5 weight / weight % to about 45 weight / weight %, about 5 weight / weight % to about 55 weight / weight %, about 5 weight / weight % to about 65 weight / weight %, about 5 weight / weight % to about 75 weight / weight %, about 5 weight / weight % to about 85 weight / weight %, about 5 weight / weight % to about 95 weight / weight %, about 5 weight / weight % to about 100 weight / weight %, about 15 weight / weight % to about 25 weight / weight %, about 15 weight / weight % to about 35 weight / weight %, about 15 weight / weight % to about 45 weight / weight %, about 15 weight / weight % to about 55 weight / weight %, about 15 weight / weight % to about 65 weight / weight %, about 15 weight / weight % to about 75 weight / weight %, about 15 weight / weight % to about 95 weight / weight %, about 15 weight / weight % to about 100 weight / weight %, about 25 weight / weight % to about 35 weight / weight %, about 25 weight / weight % to about 45 weight / weight %, about 25 weight / weight % to about 55 weight / weight %, about 25 weight / weight % to about 65 weight / weight %, about 25 weight / weight % to about 75 weight / weight %, about 25 weight / weight % to about 85 weight / weight %, about 25 weight / weight % to about 95 weight / weight %, about 25 weight / weight % to about 100 weight / weight %, about 35 weight / weight % to about 45 weight / weight %, about 35 weight / weight % to about 55 weight / weight %, about 35 weight / weight % to about 65 weight / weight %, about 35 weight / weight % to about 75 weight / weight %, about 35 weight / weight % to about 85 weight / weight %, about 35 weight / weight % to about 95 weight / weight %, about 35 weight / weight % to about 100 weight / weight %, about 45 weight / weight % to about 55 weight / weight %, about 45 weight / weight % to about 65 weight / weight %, about 45 weight / weight % to about 75 weight / weight %, about 45 weight / weight % to about 85 weight / weight %, about 45 weight / weight % to about 95 weight / weight %, about 45 weight / weight % to about 100 weight / weight %, about 55 weight / weight % to about 65 weight / weight %, about 55 weight / weight % to about 75 weight / weight %, about 55 weight / weight % to about 85 weight / weight %, about 55 weight / weight % to about 95 weight / weight %, about 55 weight / weight % to about 100 weight / weight %, about 65 weight / weight % to about 75 weight / weight %, about 65 weight / weight % to about 85 weight / weight %, about 65 weight / weight % to about 95 weight / weight %, about 65 weight / weight % to about 100 weight / weight %, about 75 weight / weight % to about 85 weight / weight %, about 75 weight / weight % to about 95 weight / weight %, about 75 weight / weight % to about 100 weight / weight %, about 85 weight / weight % to about 95 weight / weight %, about 85 weight / weight % to about 100 weight / weight %, or about 95 weight / weight % to about 100 weight / weight % of one or more elastomers.about 45 wt / wt% to about 85 wt / wt%, about 45 wt / wt% to about 95 wt / wt%, about 45 wt / wt% to about 100 wt / wt%, about 55 wt / wt% to about 65 wt / wt%, about 55 wt / wt% to about 75 wt / wt%, about 55 wt / wt% to about 85 wt / wt%, about 55 wt / wt% to about 95 wt / wt%, about 55 wt / wt% to about 100 wt / wt%, about 65 wt / wt% to about 75 wt / wt%, about 65 wt / wt% to about 85 wt / wt%, about 65 wt / wt% to about 95 wt / wt%, about 65 wt / wt% to about 100 wt / wt%, about 75 wt / wt% to about 85 wt / wt%, about 75 wt / wt% to about 95 wt / wt%, about 75 wt / wt% to about 100 wt / wt%, about 85 wt / wt% to about 95 wt / wt%, or about 95 wt / wt% to about 100 wt / wt% of one or more elastomers.

[0370] In some embodiments, the composition of the present disclosure comprises about 50 wt / wt% of one or more elastomers. In some embodiments, the composition comprises about 1 wt / wt%, about 5 wt / wt%, about 10 wt / wt%, about 15 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, about 95 wt / wt%, or about 100 wt / wt% of one or more elastomers.

[0371] As used herein, the term “phr” refers to parts per hundred parts of rubber by weight. The weight parts of each component are based on 100 parts by weight of the total mass of the one or more elastomers present in the composition.

[0372] In some embodiments, the composition of the present disclosure comprises about 1 phr to about 5 phr of a compound of the present disclosure. In some embodiments, the composition comprises about 0.01 phr to about 0.1 phr, about 0.01 phr to about 0.5 phr, about 0.01 phr to about 1 phr, about 0.01 phr to about 2 phr, about 0.01 phr to about 3 phr, about 0.01 phr to about 4 phr, about 0.01 phr to about 5 phr, about 0.01 phr to about 7.5 phr, about 0.01 phr to about 10 phr, about 0.01 phr to about 20 phr, about 0.1 phr to about 0.5 phr, about 0.1 phr to about 1 phr, about 0.1 phr to about 2 phr, about 0.1 phr to about 3 phr, about 0.1 phr to about 4 phr, about 0.1 phr to about 5 phr, about 0.1 phr to about 7.5 phr, about 0.1 phr to about 10 phr, about 0.1 phr to about 20 phr, about 1 phr to about 2 phr, about 1 phr to about 3 phr, about 1 phr to about 4 phr, about 1 phr to about 7.5 phr, about 1 phr to about 10 phr, about 1 phr to about 20 phr, about 2 phr to about 3 phr, about 2 phr to about 4 phr, about 2 phr to about 5 phr, about 2 phr to about 7.5 phr, about 2 phr to about 10 phr, about 2 phr to about 20 phr, about 3 phr to about 4 phr, about 3 phr to about 5 phr, about 3 phr to about 7.5 phr, about 3 phr to about 10 phr, about 3 phr to about 20 phr, about 4 phr to about 5 phr, about 4 phr to about 7.5 phr, about 4 phr to about 10 phr, about 4 phr to about 20 phr, about 5 phr to about 7.5 phr, about 5 phr to about 10 phr, about 5 phr to about 20 phr, about 7.5 phr to about 10 phr, about 7.5 phr to about 20 phr, or about 10 phr to about 20 phr of a compound of the present disclosure.

[0373] In some embodiments, the composition of the present disclosure comprises about 3 phr of a compound of the present 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 present disclosure.

[0374] In some embodiments, the composition of the present disclosure comprises a compound of the present disclosure and one or more fillers.

[0375] As used herein, the term "filler" is a substance that enhances or imparts other properties to an elastomeric composition, including but not limited to increasing the volume of the composition. Non-limiting examples of fillers include carbon black, silica, kaolin, calcium silicate, talc, carbon nanotubes (CNTs), carbon fiber (HCF), graphite, graphene, aluminosilicates, starch, and fibers, and combinations thereof.

[0376] In some embodiments, the filler is derived from a natural source. For example, the silica can be derived from rice hulls.

[0377] In some embodiments, the composition of the present disclosure comprises about 15 weight / weight % to about 85 weight / weight % of one or more fillers. In some embodiments, the composition comprises about 1 weight / weight % to about 5 weight / weight %, about 1 weight / weight % to about 15 weight / weight %, about 1 weight / weight % to about 25 weight / weight %, about 1 weight / weight % to about 35 weight / weight %, about 1 weight / weight % to about 45 weight / weight %, about 1 weight / weight % to about 55 weight / weight %, about 1 weight / weight % to about 65 weight / weight %, about 1 weight / weight % to about 75 weight / weight %, about 1 weight / weight % to about 85 weight / weight %, about 1 weight / weight % to about 95 weight / weight %, about 5 weight / weight % to about 15 weight / weight %, about 5 weight / weight % to about 25 weight / weight %, about 5 weight / weight % to about 35 weight / weight %, about 5 weight / weight % to about 45 weight / weight %, about 5 weight / weight % to about 55 weight / weight %, about 5 weight / weight % to about 65 weight / weight %, about 5 weight / weight % to about 75 weight / weight %, about 5 weight / weight % to about 85 weight / weight %, about 5 weight / weight % to about 95 weight / weight %, about 15 weight / weight % to about 25 weight / weight %, about 15 weight / weight % to about 35 weight / weight %, about 15 weight / weight % to about 45 weight / weight %, about 15 weight / weight % to about 55 weight / weight %, about 15 weight / weight % to about 65 weight / weight %, about 15 weight / weight % to about 75 weight / weight %, about 15 weight / weight % to about 95 weight / weight %, about 25 weight / weight % to about 35 weight / weight %, about 25 weight / weight % to about 45 weight / weight %, about 25 weight / weight % to about 55 weight / weight %, about 25 weight / weight % to about 65 weight / weight %, about 25 weight / weight % to about 75 weight / weight %, about 25 weight / weight % to about 85 weight / weight %, about 25 weight / weight % to about 95 weight / weight %, about 35 weight / weight % to about 45 weight / weight %, about 35 weight / weight % to about 55 weight / weight %, about 35 weight / weight % to about 65 weight / weight %, about 35 weight / weight % to about 75 weight / weight %, about 35 weight / weight % to about 85 weight / weight %, about 35 weight / weight % to about 95 weight / weight %, about 45 weight / weight % to about 55 weight / weight %, about 45 weight / weight % to about 65 weight / weight %, about 45 weight / weight % to about 75 weight / weight %, about 45 weight / weight % to about 85 weight / weight %, about 45 weight / weight % to about 95 weight / weight %, about 55 weight / weight % to about 65 weight / weight %, about 55 weight / weight % to about 75 weight / weight %, about 55 weight / weight % to about 85 weight / weight %, about 55 weight / weight % to about 95 weight / weight %,about 65% to about 75% by weight / weight, about 65% to about 85% by weight / weight, about 65% to about 95% by weight / weight, about 75% to about 85% by weight / weight, about 75% to about 95% by weight / weight, or about 85% to about 95% by weight / weight of one or more fillers.

[0378] In some embodiments, the compositions of the present disclosure comprise about 50% by weight / weight of one or more fillers. In some embodiments, the compositions comprise about 1% by weight / weight, about 5% by weight / weight, about 10% by weight / weight, about 15% by weight / weight, about 20% by weight / weight, about 25% by weight / weight, about 30% by weight / weight, about 35% by weight / weight, about 40% by weight / weight, about 45% by weight / weight, about 55% by weight / weight, about 60% by weight / weight, about 65% by weight / weight, about 70% by weight / weight, about 75% by weight / weight, about 80% by weight / weight, about 85% by weight / weight, about 90% by weight / weight, or about 95% by weight / weight of one or more fillers.

[0379] In some embodiments, the composition of the present disclosure comprises about 30 phr to about 500 phr of one or more fillers. In some embodiments, the composition comprises about 30 phr to about 50 phr, about 30 phr to about 100 phr, about 30 phr to about 150 phr, about 30 phr to about 200 phr, about 30 phr to about 250 phr, about 30 phr to about 300 phr, about 30 phr to about 350 phr, about 30 phr to about 400 phr, about 30 phr to about 450 phr, about 30 phr to about 500 phr, about 50 phr to about 100 phr, about 50 phr to about 150 phr, about 50 phr to about 200 phr, about 50 phr to about 250 phr, about 50 phr to about 300 phr, about 50 phr to about 350 phr, about 50 phr to about 400 phr, about 50 phr to about 450 phr, about 50 phr to about 500 phr, about 100 phr to about 150 phr, about 100 phr to about 200 phr, about 100 phr to about 250 phr, about 100 phr to about 300 phr, about 100 phr to about 350 phr, about 100 phr to about 400 phr, about 100 phr to about 450 phr, about 100 phr to about 500 phr, about 150 phr to about 200 phr, about 150 phr to about 250 phr, about 150 phr to about 300 phr, about 150 phr to about 350 phr, about 150 phr to about 400 phr, about 150 phr to about 450 phr, about 150 phr to about 500 phr, about 200 phr to about 250 phr, about 200 phr to about 300 phr, about 200 phr to about 350 phr, about 200 phr to about 400 phr, about 200 phr to about 450 phr, about 200 phr to about 500 phr, about 250 phr to about 300 phr, about 250 phr to about 350 phr, about 250 phr to about 400 phr, about 250 phr to about 450 phr, about 250 phr to about 500 phr, about 300 phr to about 350 phr, about 300 phr to about 400 phr, about 300 phr to about 450 phr, about 300 phr to about 500 phr, about 350 phr to about 400 phr, about 350 phr to about 450 phr, about 350 phr to about 500 phr, about 400 phr to about 450 phr, about 400 phr to about 500 phr, or about 450 phr to about 500 phr of one or more fillers.

[0380] In some embodiments, the composition of the present 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.

[0381] In some embodiments, the composition of the present disclosure comprises a compound of the present disclosure and one or more rubber chemicals. As used herein, the term “rubber chemical” refers to a compound or substance used to facilitate vulcanization of rubber. Rubber chemicals include, but are not limited to, vulcanizing agents, accelerators, activators, and prevulcanization inhibitors.

[0382] As used herein, the term “vulcanization” and the like refer to a process in which crosslinks are formed between elastomers to affect changes in the material properties of the elastomers. Specifically, vulcanization generally increases the rigidity and durability of the elastomers. Vulcanization is carried out at room temperature or at high temperature, depending on the properties of the elastomer(s), filler(s), and rubber chemical(s) used. The term “curing” is also used in the art to describe this process.

[0383] As used herein, the term “vulcanizing agent” refers to any substance that effects crosslinks between elastomers. Vulcanizing agents can effect crosslinks between individual polymer chains of an elastomer through various mechanisms, including but not limited to, by forming covalent bonds between the vulcanizing agent and two or more individual polymer chains, or by generating free radical species on individual polymer chains that can combine to form covalent bonds between two polymer chains. Non-limiting examples of vulcanizing agents include sulfur, peroxides, vulcanized vegetable oils, greases, and resins. Non-limiting examples of sulfur include octasulfur (S8), cyclododecasulfur (S 12 ), 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), 4,4-di(tert-butylperoxy)butyl valerate (VAL), and 1,1-di(tert-butylperoxy)-3,3,5-trimethylcyclohexane (TMC). Non-limiting examples of resins include adhesive resins. As used herein, the term “adhesive resin” refers to a chemical that reacts with a methylene donor, such as hexamethylenetetramine (HMTA) or hexamethoxymethyl melamine (HMMM), to facilitate adhesion, such as resorcinol formaldehyde resin and phenolic resin.

[0384] As used herein, the term “accelerator” refers to any substance that increases the kinetics of vulcanization. In some embodiments, the accelerator enables vulcanization to occur at lower temperatures and / or more effectively utilizes the vulcanizing agent (e.g., sulfur). Non-limiting examples of accelerators include guanidines, thiazoles, sulfenamides, dithiocarbamates, xanthates, and thiophosphates. Non-limiting examples of guanidines include diphenyl guanidine (DPG). Non-limiting examples of thiazoles include 2-mercaptobenzothiazole (MBT), zinc 2-mercaptobenzothiazole (ZMBT), mercaptobenzothiazole disulfide (MBTS), and N-tert-butyl-2-benzothiazyl sulfenamide (TBSI). Non-limiting examples of sulfenamides include N-tert-butyl-2-benzothiazyl sulfenamide (TBBS), N-cyclohexylbenzothiazole-2-sulfenamide (CBS), dicyclohexyl-2-benzothiazyl sulfenamide (DCBS), N-oxydiethylenebenzothiazyl sulfenamide (OBTS), N-oxydiethylene thiocarbamoyl-N'-oxydiethylene sulfenamide (OTOS), and thiocarbamoyl sulfenamide. Non-limiting examples of dithiocarbamates include zinc dimethyl dithiocarbamate (ZDMC), zinc diethyl dithiocarbamate (ZDEC), zinc dibutyl dithiocarbamate (ZDBC), nickel dibutyl dithiocarbamate (NDBC), sodium dibenzyl dithiocarbamate (SBEC), sodium diethyl dithiocarbamate (SDEC), tellurium diethyl dithiocarbamate (TDEC), and zinc dibenzyl dithiocarbamate (ZEBC).

[0385] As used herein, the term “activator” refers to any substance that activates the vulcanizing agent and enables it to crosslink the elastomer as described above. The activator can function through various mechanisms, including but not limited to, by forming a chemical complex with the accelerator or by coordinating with the sulfur (when sulfur is used as the vulcanizing agent). Non-limiting examples of activators include metal oxides, acids, and metal complexes. 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.

[0386] As used herein, the term “prevulcanization inhibitor” refers to a compound that retards the onset and / or rate of vulcanization. These compounds are also known as “retarders.” Non-limiting examples of prevulcanization inhibitors include N-(cyclohexylthio)phthalimide (CTP), benzoic anhydride, salicylic anhydride, and phthalic anhydride.

[0387] In some embodiments, the composition of the present disclosure comprises about 15 weight / weight % to about 85 weight / weight % of one or more rubber chemicals. In some embodiments, the composition comprises about 1 weight / weight % to about 5 weight / weight %, about 1 weight / weight % to about 15 weight / weight %, about 1 weight / weight % to about 25 weight / weight %, about 1 weight / weight % to about 35 weight / weight %, about 1 weight / weight % to about 45 weight / weight %, about 1 weight / weight % to about 55 weight / weight %, about 1 weight / weight % to about 65 weight / weight %, about 1 weight / weight % to about 75 weight / weight %, about 1 weight / weight % to about 85 weight / weight %, about 1 weight / weight % to about 95 weight / weight %, about 5 weight / weight % to about 15 weight / weight %, about 5 weight / weight % to about 25 weight / weight %, about 5 weight / weight % to about 35 weight / weight %, about 5 weight / weight % to about 45 weight / weight %, about 5 weight / weight % to about 55 weight / weight %, about 5 weight / weight % to about 65 weight / weight %, about 5 weight / weight % to about 75 weight / weight %, about 5 weight / weight % to about 85 weight / weight %, about 5 weight / weight % to about 95 weight / weight %, about 15 weight / weight % to about 25 weight / weight %, about 15 weight / weight % to about 35 weight / weight %, about 15 weight / weight % to about 45 weight / weight %, about 15 weight / weight % to about 55 weight / weight %, about 15 weight / weight % to about 65 weight / weight %, about 15 weight / weight % to about 75 weight / weight %, about 15 weight / weight % to about 95 weight / weight %, about 25 weight / weight % to about 35 weight / weight %, about 25 weight / weight % to about 45 weight / weight %, about 25 weight / weight % to about 55 weight / weight %, about 25 weight / weight % to about 65 weight / weight %, about 25 weight / weight % to about 75 weight / weight %, about 25 weight / weight % to about 85 weight / weight %, about 25 weight / weight % to about 95 weight / weight %, about 35 weight / weight % to about 45 weight / weight %, about 35 weight / weight % to about 55 weight / weight %, about 35 weight / weight % to about 65 weight / weight %, about 35 weight / weight % to about 75 weight / weight %, about 35 weight / weight % to about 85 weight / weight %, about 35 weight / weight % to about 95 weight / weight %, about 45 weight / weight % to about 55 weight / weight %, about 45 weight / weight % to about 65 weight / weight %, about 45 weight / weight % to about 75 weight / weight %, about 45 weight / weight % to about 85 weight / weight %, about 45 weight / weight % to about 95 weight / weight %, about 55 weight / weight % to about 65 weight / weight %, about 55 weight / weight % to about 75 weight / weight %, about 55 weight / weight % to about 85 weight / weight %, about 55 weight / weight % to about 95 weight / weight %, about 65 weight / weight % to about 75 weight / weight %, about 65 weight / weight % to about 85 weight / weight %, about 65 weight / weight % to about 95 weight / weight %, about 75 weight / weight % to about 85 weight / weight %, about 75 weight / weight % to about 95 weight / weight %, or about 85 weight / weight % to about 95 weight / weight % of one or more rubber chemicals.about 65 wt / wt% to about 85 wt / wt%, about 65 wt / wt% to about 95 wt / wt%, about 75 wt / wt% to about 85 wt / wt%, about 75 wt / wt% to about 95 wt / wt%, or about 85 wt / wt% to about 95 wt / wt% of one or more rubber chemicals.

[0388] In some embodiments, the composition of the present 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.

[0389] In some embodiments, the composition of the present disclosure comprises about 1 phr to about 20 phr of one or more rubber chemicals. In some embodiments, the composition comprises about 0.1 phr to about 1 phr, about 0.1 phr to about 5 phr, about 0.1 phr to about 10 phr, about 0.1 phr to about 15 phr, about 0.1 phr to about 20 phr, about 0.1 phr to about 25 phr, about 0.1 phr to about 30 phr, about 0.1 phr to about 35 phr, about 0.1 phr to about 40 phr, about 1 phr to about 5 phr, about 1 phr to about 10 phr, about 1 phr to about 15 phr, about 1 phr to about 25 phr, about 1 phr to about 30 phr, about 1 phr to about 35 phr, about 1 phr to about 40 phr, about 5 phr to about 10 phr, about 5 phr to about 15 phr, about 5 phr to about 20 phr, about 5 phr to about 25 phr, about 5 phr to about 30 phr, about 5 phr to about 35 phr, about 5 phr to about 40 phr, about 10 phr to about 15 phr, about 10 phr to about 20 phr, about 10 phr to about 25 phr, about 10 phr to about 30 phr, about 10 phr to about 35 phr, about 10 phr to about 40 phr, about 15 phr to about 20 phr, about 15 phr to about 25 phr, about 15 phr to about 30 phr, about 15 phr to about 35 phr, about 15 phr to about 40 phr, about 20 phr to about 25 phr, about 20 phr to about 30 phr, about 20 phr to about 35 phr, about 20 phr to about 40 phr, about 25 phr to about 30 phr, about 25 phr to about 35 phr, about 25 phr to about 40 phr, about 30 phr to about 35 phr, about 30 phr to about 40 phr, or about 35 phr to about 40 phr of one or more rubber chemicals.

[0390] In some embodiments, the composition of the present 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.

[0391] As used herein, the term “plasticizer” refers to a processing aid used to reduce the viscosity of the composition, increase the plasticity of the composition, and / or increase the volume of the composition. Plasticizers aid in the process of mixing and forming the composition comprising the elastomer prior to vulcanization of the composition. Non-limiting examples of plasticizers include mineral oils (paraffinic, aromatic, or naphthenic oils), organic esters, resins, waxes, ester-based plasticizers, and oils of natural origin, such as soybean oil, vegetable oil, or orange oil.

[0392] In some embodiments, the compositions of the present disclosure comprise about 15% to about 85% by weight / weight of one or more plasticizers. In some embodiments, the compositions comprise about 1% to about 5% by weight / weight, about 1% to about 15% by weight / weight, about 1% to about 25% by weight / weight, about 1% to about 35% by weight / weight, about 1% to about 45% by weight / weight, about 1% to about 55% by weight / weight, about 1% to about 65% by weight / weight, about 1% to about 75% by weight / weight, about 1% to about 85% by weight / weight, about 1% to about 95% by weight / weight, about 5% to about 15% by weight / weight, about 5% to about 25% by weight / weight, about 5% to about 35% by weight / weight, about 5% to about 45% by weight / weight, about 5% to about 55% by weight / weight, about 5% to about 65% by weight / weight, about 5% to about 75% by weight / weight, about 5% to about 85% by weight / weight, about 5% to about 95% by weight / weight, about 15% to about 25% by weight / weight, about 15% to about 35% by weight / weight, about 15% to about 45% by weight / weight, about 15% to about 55% by weight / weight, about 15% to about 65% by weight / weight, about 15% to about 75% by weight / weight, about 15% to about 95% by weight / weight, about 25% to about 35% by weight / weight, about 25% to about 45% by weight / weight, about 25% to about 55% by weight / weight, about 25% to about 65% by weight / weight, about 25% to about 75% by weight / weight, about 25% to about 85% by weight / weight, about 25% to about 95% by weight / weight, about 35% to about 45% by weight / weight, about 35% to about 55% by weight / weight, about 35% to about 65% by weight / weight, about 35% to about 75% by weight / weight, about 35% to about 85% by weight / weight, about 35% to about 95% by weight / weight, about 45% to about 55% by weight / weight, about 45% to about 65% by weight / weight, about 45% to about 75% by weight / weight, about 45% to about 85% by weight / weight, about 45% to about 95% by weight / weight, about 55% to about 65% by weight / weight, about 55% to about 75% by weight / weight, about 55% to about 85% by weight / weight,about 65 wt / wt% to about 75 wt / wt%, about 65 wt / wt% to about 85 wt / wt%, about 65 wt / wt% to about 95 wt / wt%, about 75 wt / wt% to about 85 wt / wt%, about 75 wt / wt% to about 95 wt / wt%, or about 85 wt / wt% to about 95 wt / wt% of one or more plasticizers.

[0393] In some embodiments, the compositions of the present disclosure comprise about 15 wt / wt% of one or more plasticizers. In some embodiments, the compositions comprise 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.

[0394] In some embodiments, the composition of the present disclosure comprises about 1 phr to about 20 phr of one or more plasticizers. In some embodiments, the composition comprises about 0.1 phr to about 1 phr, about 0.1 phr to about 5 phr, about 0.1 phr to about 10 phr, about 0.1 phr to about 15 phr, about 0.1 phr to about 20 phr, about 0.1 phr to about 25 phr, about 0.1 phr to about 30 phr, about 0.1 phr to about 35 phr, about 0.1 phr to about 40 phr, about 1 phr to about 5 phr, about 1 phr to about 10 phr, about 1 phr to about 15 phr, about 1 phr to about 25 phr, about 1 phr to about 30 phr, about 1 phr to about 35 phr, about 1 phr to about 40 phr, about 5 phr to about 10 phr, about 5 phr to about 15 phr, about 5 phr to about 20 phr, about 5 phr to about 25 phr, about 5 phr to about 30 phr, about 5 phr to about 35 phr, about 5 phr to about 40 phr, about 10 phr to about 15 phr, about 10 phr to about 20 phr, about 10 phr to about 25 phr, about 10 phr to about 30 phr, about 10 phr to about 35 phr, about 10 phr to about 40 phr, about 15 phr to about 20 phr, about 15 phr to about 25 phr, about 15 phr to about 30 phr, about 15 phr to about 35 phr, about 15 phr to about 40 phr, about 20 phr to about 25 phr, about 20 phr to about 30 phr, about 20 phr to about 35 phr, about 20 phr to about 40 phr, about 25 phr to about 30 phr, about 25 phr to about 35 phr, about 25 phr to about 40 phr, about 30 phr to about 35 phr, about 30 phr to about 40 phr, or about 35 phr to about 40 phr of one or more plasticizers.

[0395] In some embodiments, the composition of the present 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.

[0396] In some embodiments, the compositions of the present disclosure further comprise one or more additional anti-degradants that are not compounds of the present disclosure. In some embodiments, the one or more additional anti-degradants are antioxidants. In some embodiments, the one or more additional anti-degradants are anti-ozonants. In some embodiments, the one or more additional anti-degradants are heat stabilizers, light stabilizers, or fatigue crack stabilizers. Non-limiting examples of anti-degradants include p-phenylenediamine (PPD), trimethyl-dihydroquinoline (TMQ), phenols or hindered phenols, alkylated diphenylamine (DPA), diphenylamine-ketone condensates, quinones, hydroquinones, amines, hindered amines, paraffin or microcrystalline waxes, and / or natural anti-degradants. Non-limiting examples of PPDs include N 1 -(4-methylpentan-2-yl)-N 4 -phenylbenzene-1,4-diamine (6PPD), N-(1,4-dimethylpentyl)-N'-phenyl-p-phenylenediamine (7PPD), N-sec-octyl-N'-phenyl-p-phenylenediamine (8PPD), N 1 -phenyl-N 4 -(prop-2-yl)benzene-1,4-diamine (IPPD), N,N'-di-sec-butyl-p-phenylenediamine (44PD), N,N'-bis(1,3-dimethylbutyl)-p-phenylenediamine (66PD), N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine (77PD), and N-N'-dioctyl-p-phenylenediamine (88PD). Non-limiting examples of TMQs include 2,2,4-trimethyl-1,2-dihydroquinoline and oligomers or polymers thereof.

[0397] In some embodiments, the compositions of the present disclosure comprise about 15% to about 85% by weight / weight of one or more additional anti-degrading agents. In some embodiments, the compositions comprise about 1% to about 5%, about 1% to about 15%, about 1% to about 25%, about 1% to about 35%, about 1% to about 45%, about 1% to about 55%, about 1% to about 65%, about 1% to about 75%, about 1% to about 85%, about 1% to about 95%, about 5% to about 15%, about 5% to about 25%, about 5% to about 35%, about 5% to about 45%, about 5% to about 55%, about 5% to about 65%, about 5% to about 75%, about 5% to about 85%, about 5% to about 95%, about 15% to about 25%, about 15% to about 35%, about 15% to about 45%, about 15% to about 55%, about 15% to about 65%, about 15% to about 75%, about 15% to about 95%, about 25% to about 35%, about 25% to about 45%, about 25% to about 55%, about 25% to about 65%, about 25% to about 75%, about 25% to about 85%, about 25% to about 95%, about 35% to about 45%, about 35% to about 55%, about 35% to about 65%, about 35% to about 75%, about 35% to about 85%, about 35% to about 95%, about 45% to about 55%, about 45% to about 65%, about 45% to about 75%, about 45% to about 85%, about 45% to about 95%, about 55% to about 65%, about 55% to about 75%, about 55% to about 85%, about 55% to about 95%, about 65% to about 75%, about 65% to about 85%, about 65% to about 95%, about 75% to about 85%, about 75% to about 95%, or about 85% to about 95% by weight / weight of one or more additional anti-degrading agents.about 65 wt / wt% to about 75 wt / wt%, about 65 wt / wt% to about 85 wt / wt%, about 65 wt / wt% to about 95 wt / wt%, about 75 wt / wt% to about 85 wt / wt%, about 75 wt / wt% to about 95 wt / wt%, or about 85 wt / wt% to about 95 wt / wt% of one or more additional anti-degradants.

[0398] In some embodiments, the composition of the present disclosure comprises about 15 wt / wt% of one or more additional anti-degradants. In some embodiments, the composition comprises about 1 wt / wt%, about 5 wt / wt%, about 10 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt% of one or more additional anti-degradants.

[0399] In some embodiments, the composition of the present disclosure comprises about 1 to about 5 phr of one or more additional anti-degradants. In some embodiments, the composition comprises about 0.001 phr to about 0.01 phr, about 0.001 phr to about 0.1 phr, about 0.001 phr to about 1 phr, about 0.001 phr to about 5 phr, about 0.001 phr to about 7.5 phr, about 0.001 phr to about 10 phr, about 0.01 phr to about 0.1 phr, about 0.01 phr to about 1 phr, about 0.01 phr to about 5 phr, about 0.01 phr to about 7.5 phr, about 0.01 phr to about 10 phr, about 0.1 phr to about 1 phr, about 0.1 phr to about 5 phr, about 0.1 phr to about 7.5 phr, about 0.1 phr to about 10 phr, about 1 phr to about 7.5 phr, about 1 phr to about 10 phr, about 5 phr to about 7.5 phr, about 5 phr to about 10 phr, or about 7.5 phr to about 10 phr of one or more additional anti-degradants.

[0400] In some embodiments, the composition of the present 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.

[0401] In some embodiments, the present disclosure provides a composition comprising a compound of the present disclosure and one or more carriers. As used herein, the term "carrier" refers to a solid that can absorb 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 less than 500 microns in diameter.

[0402] In some embodiments, the composition comprises about 15% to about 85% w / w of one or more carriers. In some embodiments, the composition comprises about 1% to about 5% w / w, about 1% to about 15% w / w, about 1% to about 25% w / w, about 1% to about 35% w / w, about 1% to about 45% w / w, about 1% to about 55% w / w, about 1% to about 65% w / w, about 1% to about 75% w / w, about 1% to about 85% w / w, about 1% to about 95% w / w, about 5% to about 15% w / w, about 5% to about 25% w / w, about 5% to about 35% w / w, about 5% to about 45% w / w, about 5% to about 55% w / w, about 5% to about 65% w / w, about 5% to about 75% w / w, about 5% to about 85% w / w, about 5% to about 95% w / w, about 15% to about 25% w / w, about 15% to about 35% w / w, about 15% to about 45% w / w, about 15% to about 55% w / w, about 15% to about 65% w / w, about 15% to about 75% w / w, about 15% to about 95% w / w, about 25% to about 35% w / w, about 25% to about 45% w / w, about 25% to about 55% w / w, about 25% to about 65% w / w, about 25% to about 75% w / w, about 25% to about 85% w / w, about 25% to about 95% w / w, about 35% to about 45% w / w, about 35% to about 55% w / w, about 35% to about 65% w / w, about 35% to about 75% w / w, about 35% to about 85% w / w, about 35% to about 95% w / w, about 45% to about 55% w / w, about 45% to about 65% w / w, about 45% to about 75% w / w, about 45% to about 85% w / w, about 45% to about 95% w / w, about 55% to about 65% w / w, about 55% to about 75% w / w, about 55% to about 85% w / w, about 55% to about 95% w / w, about 65% to about 75% w / w, about 65% to about 85% w / w, about 65% to about 95% w / w, about 75% to about 85% w / w, about 75% to about 95% w / w, or about 85% to about 95% w / w of one or more carriers.about 65% to about 75% by weight / weight, about 65% to about 85% by weight / weight, about 65% to about 95% by weight / weight, about 75% to about 85% by weight / weight, about 75% to about 95% by weight / weight, or about 85% to about 95% by weight / weight of one or more carriers.

[0403] In some embodiments, the composition comprises about 15% by weight / weight of one or more carriers. In some embodiments, the composition comprises about 1% by weight / weight, about 5% by weight / weight, about 10% by weight / weight, about 20% by weight / weight, about 25% by weight / weight, about 30% by weight / weight, about 35% by weight / weight, about 40% by weight / weight, about 45% by weight / weight, about 50% by weight / weight, about 55% by weight / weight, about 60% by weight / weight, about 65% by weight / weight, about 70% by weight / weight, about 75% by weight / weight, about 80% by weight / weight, about 85% by weight / weight, about 90% by weight / weight, or about 95% by weight / weight of one or more carriers.

[0404] The present disclosure also provides a method for making a composition comprising a compound of the present disclosure and one or more carriers, the method comprising mixing the compound and one or more carriers.

[0405] The present disclosure also provides a lubricant composition comprising a compound of the present disclosure and a lubricant. Non-limiting examples of lubricants include mineral oils, higher molecular weight petroleum fractions such as aromatic, naphthenic, and paraffinic fractions, synthetic oils such as polyalphaolefins (PAO), synthetic esters, polyalkylene glycols (PAG), phosphate esters, perfluoropolyethers (PFPE), alkylated naphthalenes (AN), silicate esters, ionic fluids, and multi-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 bio-lubricants such as triglycerides, high oleic rapeseed oil, castor oil, palm oil, sunflower oil, and rapeseed oil.

[0406] The present disclosure also provides a combustible fuel composition comprising a combustible fuel and a compound of the present disclosure. Non-limiting examples of combustible fuels include gasoline, diesel, kerosene, liquefied petroleum gas, synthetic fuels, and biodiesel.

[0407] The present disclosure also provides fuel additive compositions comprising a fuel additive and a compound of the present disclosure. Non-limiting examples of fuel additives include oxygenates (such as alcohols and ethers), antioxidants, stabilizers, detergents, antiknock agents, lead scavengers, fuel dyes, viscosity improvers, and butyl rubber. In some embodiments, the butyl rubber is in the form of polyisobutylene succinimides. In some embodiments, butyl rubber is added as a detergent to prevent diesel injector fouling.

[0408] In some embodiments, the present disclosure provides the compositions recited in Table 2.

[0409] Table 2

[0410]

[0411] In some embodiments, the vulcanized tire or other rubber article compositions of Table 2 comprise about 0.1 weight / weight %, about 0.2 weight / weight %, about 0.3 weight / weight %, about 0.4 weight / weight %, about 0.5 weight / weight %, about 0.6 weight / weight %, about 0.7 weight / weight %, about 0.8 weight / weight %, about 0.9 weight / weight %, about 1 weight / weight %, about 2 weight / weight %, about 3 weight / weight %, about 4 weight / weight %, about 5 weight / weight %, about 6 weight / weight %, about 7 weight / weight %, about 8 weight / weight %, about 9 weight / weight %, or about 10 weight / weight % of a compound of the present disclosure. In some embodiments, the vulcanized tire or other rubber article of Table 2 comprises about 5 weight / weight %, about 10 weight / weight %, about 15 weight / weight %, about 20 weight / weight %, about 25 weight / weight %, about 30 weight / weight %, about 35 weight / weight %, about 40 weight / weight %, about 45 weight / weight %, about 50 weight / weight %, about 55 weight / weight %, about 60 weight / weight %, about 65 weight / weight %, about 70 weight / weight %, about 75 weight / weight %, about 80 weight / weight %, about 85 weight / weight %, about 90 weight / weight %, or about 95 weight / weight % of at least one elastomer.

[0412] In some embodiments, the unvulcanized tire inner component or assembled component or other end use component composition of Table 2 comprises about 0.01 weight / weight %, about 0.02 weight / weight %, about 0.03 weight / weight %, about 0.04 weight / weight %, about 0.05 weight / weight %, about 0.06 weight / weight %, about 0.07 weight / weight %, about 0.08 weight / weight %, about 0.09 weight / weight %, about 0.1 weight / weight %, about 0.2 weight / weight %, about 0.3 weight / weight %, about 0.4 weight / weight %, about 0.5 weight / weight %, about 0.6 weight / weight %, about 0.7 weight / weight %, about 0.8 weight / weight %, about 0.9 weight / weight %, about 1 weight / weight %, about 2 weight / weight %, about 3 weight / weight %, about 4 weight / weight %, about 5 weight / weight %, about 6 weight / weight %, about 7 weight / weight %, about 8 weight / weight %, about 9 weight / weight %, or about 10 weight / weight % of a compound of the present disclosure. In some embodiments, the unvulcanized tire inner component or assembled component or other end use component composition of Table 2 comprises about 5 weight / weight %, about 10 weight / weight %, about 15 weight / weight %, about 20 weight / weight %, about 25 weight / weight %, about 30 weight / weight %, about 35 weight / weight %, about 40 weight / weight %, about 45 weight / weight %, about 50 weight / weight %, about 55 weight / weight %, about 60 weight / weight %, about 65 weight / weight %, about 70 weight / weight %, about 75 weight / weight %, about 80 weight / weight %, about 85 weight / weight %, about 90 weight / weight %, or about 95 weight / weight % of at least one elastomer.

[0413] Vulcanized elastomeric articles

[0414] The present disclosure also provides vulcanized elastomeric articles comprising a compound of the present disclosure. The term “vulcanized elastomeric article” refers to an article made by forming a composition comprising an elastomer into a particular shape and vulcanizing the composition to provide the article.

[0415] The present disclosure also provides vulcanized elastomeric articles prepared using the compositions described herein.

[0416] In some embodiments, the vulcanized elastomeric article is prepared by mixing a compound of the present disclosure, one or more elastomers, and optionally one or more fillers, one or more rubber chemicals, one or more plasticizers, and / or one or more additional anti-degradants, and vulcanizing the mixture to yield the vulcanized article.

[0417] In some embodiments, the vulcanized elastomeric article is a tire. In some embodiments, the tire is a passenger car tire, a light truck tire, a heavy truck or bus tire, a motorcycle tire, an agricultural tire, a bulldozer tire, an aircraft tire, or a racing tire.

[0418] 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, a sub tread, or a tread.

[0419] In some embodiments, the vulcanized elastomeric article is a rubber overshoe, a weather strip, an acoustical tile, an air spring, a bellows, a diaphragm, a tactile sensor, a cushion pad, a hose, a conveyor belt, or a flooring material.

[0420] Vehicle

[0421] In some embodiments, the present disclosure also provides a vehicle comprising a vulcanized elastomeric article (e.g., a tire), wherein the vulcanized elastomeric article comprises a compound of the present disclosure.

[0422] In some embodiments, the present disclosure also provides a vehicle comprising a vulcanized elastomeric article (e.g., a tire), wherein the vulcanized elastomeric article is prepared using a composition described herein.

[0423] In some embodiments, the vehicle is a passenger car, a light truck, a heavy truck or bus, a motorcycle, a tractor, a bulldozer, an aircraft, or a racing vehicle.

[0424] Method

[0425] The present disclosure also provides a method for preparing a vulcanized elastomeric article, the method comprising:

[0426] (a) forming a composition described herein into a shaped form; and

[0427] (b) vulcanizing the shaped form,

[0428] to provide a vulcanized elastomeric article.

[0429] In some embodiments, the vulcanization is performed at an average temperature of about 140 °C to about 160 °C. In some embodiments, the vulcanization is performed at an average temperature of about 80 °C to about 100 °C, about 80 °C to about 120 °C, about 80 °C to about 140 °C, about 80 °C to about 160 °C, about 80 °C to about 180 °C, about 80 °C to about 200 °C, about 100 °C to about 120 °C, about 100 °C to about 140 °C, about 100 °C to about 160 °C, about 100 °C to about 180 °C, about 100 °C to about 200 °C, about 120 °C to about 140 °C, about 120 °C to about 160 °C, about 120 °C to about 180 °C, about 120 °C to about 200 °C, about 140 °C to about 180 °C, about 140 °C to about 200 °C, about 160 °C to about 180 °C, about 160 °C to about 200 °C, or about 180 °C to about 200 °C.

[0430] In some embodiments, the vulcanization is performed at an average temperature of about 150 °C. In some embodiments, the vulcanization 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.

[0431] The present disclosure also provides a method for retreading a tire, the method comprising:

[0432] (a) applying a composition described herein to a tire;

[0433] (b) disposing a precured tread around the tire;

[0434] (c) disposing a curing envelope around the tire; and

[0435] (d) vulcanizing the tire.

[0436] Kit

[0437] The present disclosure also provides a kit comprising a composition described herein packaged, e.g., in a container, in a manner 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 elastomer composition. In some embodiments, the kit comprises a composition described herein and instructions for using the composition to make a vulcanized elastomer article. The composition can be packaged in any suitable container, such as a sealed bottle or container, with a label on the container or included in the kit describing the composition and proper use thereof.

[0438] Particular embodiments.

[0439] The present disclosure also provides the following particular embodiments.

[0440] Embodiment 1. A compound of Formula (I): (I)

[0441]

[0442] or a salt, solvate, or stereoisomer thereof, wherein:

[0443] is a single or double bond;

[0444] R 1 is selected from the group consisting of optionally substituted C1-C 12 alkyl, -CHR 1a R 1b , C3-C6cycloalkyl, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;

[0445] R 1a is selected from the group consisting of optionally substituted phenyl, C3-C6cycloalkyl, and optionally substituted 5- or 6-membered heteroaryl;

[0446] R 1b is selected from the group consisting of hydrogen and C1-C9alkyl;

[0447] R 2a , R 2b , and R 2c are independently selected from the group consisting of hydrogen, halogen, C1-C9alkyl, C1-C9haloalkyl, C3-C8cycloalkyl, C1-C8alkoxy, C1-C8alkylthio, C(=O)OR 4 , -OC(=O)R 4 , -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NHR 4 , -NR 4 R 5 , -OH, -SH, -SC(=O)R 4 , -SC(=O)SR 4 , -SC(=O)NHR 4 , -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 , -NR 4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 , 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio, and arylamino; or

[0448] R 2a and R 2c together with the two carbon atoms to which they are attached form an optionally substituted C3-C6cycloalkyl, an optionally substituted 4- to 6-membered heterocyclyl, an optionally substituted 4- to 6-membered aryl, or an optionally substituted 4- to 6-membered heteroaryl; and

[0449] R 2b is selected from the group consisting of hydrogen, halogen, C1-C9alkyl, C1-C9haloalkyl, optionally substituted C3-C8cycloalkyl, -OH, C1-C8alkoxy, -SH, C1-C8alkylthio, -C(=O)OR 4 , -OC(=O)R 4 , -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NHR 4 , -NR 4 R 5 , -SC(=O)R 4 , -SC(=O)SR 4 , -SC(=O)NHR 4 , -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 , -NR 4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 , optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio, and arylamino;

[0450] R 3a and R 3b are independently selected from the group consisting of hydrogen, halogen, C1-C9alkyl, and optionally substituted phenyl; or

[0451] R 3a and R 3b together with the carbon atom to which they are attached form a C3-C 12 cycloalkyl;

[0452] R 3c and R 3d are independently selected from the group consisting of hydrogen, halogen, C1-C9alkyl, and optionally substituted phenyl; or

[0453] R 3c and R 3dtogether with the two carbon atoms to which they are attached form a C3-C 12 cycloalkyl;

[0454] R 4 is selected from the group consisting of hydrogen and C1-C9alkyl; and

[0455] R 5 is selected from the group consisting of hydrogen and C1-C9alkyl,

[0456] with the proviso that the compound of Formula (I) is not:

[0457]

[0458] Embodiment 2. The compound of Embodiment 1 or a salt, solvate, or stereoisomer thereof, wherein R 3a , R 3b , and R 3c are independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, pentyl, hexyl, heptyl, octyl, and nonyl.

[0459] Embodiment 3. The compound of Embodiment 2 or a salt, solvate, or stereoisomer thereof, wherein R 3a , R 3b , and R 3c are methyl.

[0460] Embodiment 4. The compound of any one of Embodiments 1 to 3 or a salt, solvate, or stereoisomer thereof, wherein R 1 is optionally substituted phenyl.

[0461] Embodiment 5. The compound of any one of Embodiments 1 to 3 or a salt, solvate, or stereoisomer thereof, wherein R 1 is C1-C 12 alkyl.

[0462] Embodiment 6. The compound of any one of Embodiments 1 to 5, wherein R 2a , R 2b , and R 2c are hydrogen.

[0463] Embodiment 7. The compound of any one of Embodiments 1 to 5 or a salt, solvate, or stereoisomer thereof, having Formula (II):

[0464]

[0465] wherein R 2ahalogen, C1-C9alkyl, C1-C9haloalkyl, C3-C8cycloalkyl, C1-C8alkoxy, C1-C8alkylthio, C(=O)OR 4 4 4 5 4 5 4 4 5 4 4 4 4 5 4 4 5 4 4 5 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl.

[0466] Embodiment 8. The compound of Embodiment 7 or a salt, solvate, or stereoisomer thereof, wherein R 2a is C1-C9alkyl.

[0467] Embodiment 9. The compound of Embodiment 8 or a salt, solvate, or stereoisomer thereof, wherein R 2a is methyl.

[0468] Embodiment 10. The compound of any one of Embodiments 1 to 5 or a salt, solvate, or stereoisomer thereof, having Formula (III):

[0469]

[0470] wherein R 2b is selected from the group consisting of halogen, C1-C9alkyl, C1-C9haloalkyl, C3-C8cycloalkyl, C1-C8alkoxy, C1-C8alkylthio, C(=O)OR 4 4 4 5 4 5 4 ​​​​​​​​​​​​​​​​​​​​​​​​​, -OH, -SH, -SC(=O)R 4 R 5 , -OC(=O)R 4 , -SC(=O)SR 4 , -SC(=O)NHR 4 , -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 , -NR 4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 , a 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio, and arylamino.

[0471] Embodiment 11. The compound of Embodiment 10 or a salt, solvate, or stereoisomer thereof, wherein R 2b is C1-C9alkyl.

[0472] Embodiment 12. The compound of Embodiment 11 or a salt, solvate, or stereoisomer thereof, wherein R 2b is methyl.

[0473] Embodiment 13. The compound of any one of Embodiments 1 to 5 or a salt, solvate, or stereoisomer thereof, having Formula (IV):

[0474]

[0475] wherein R 2c is selected from the group consisting of halogen, C1-C9alkyl, C1-C9haloalkyl, C3-C8cycloalkyl, C1-C8alkoxy, C1-C8alkylthio, C(=O)OR 4 , -OC(=O)R 4 , -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NHR 4 , -NR 4 R 5 , -OH, -SH, -SC(=O)R 4 , -SC(=O)SR 4 , -SC(=O)NHR 4 , -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 , -NR4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 , 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio, and arylamino.

[0476] Embodiment 14. The compound of Embodiment 13 or a salt, solvate, or stereoisomer thereof, wherein R 2c is C1-C9alkyl.

[0477] Embodiment 15. The compound of Embodiment 14 or a salt, solvate, or stereoisomer thereof, wherein R 2c is methyl.

[0478] Embodiment 16. The compound of any one of Embodiments 1 to 5 or a salt, solvate, or stereoisomer thereof, having Formula (V):

[0479]

[0480] wherein R 2a and R 2b are independently selected from the group consisting of halogen, C1-C9alkyl, C1-C9haloalkyl, C3-C8cycloalkyl, C1-C8alkoxy, C1-C8alkylthio, C(=O)OR 4 , -OC(=O)R 4 , -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NHR 4 , -NR 4 R 5 , -OH, -SH, -SC(=O)R 4 , -SC(=O)SR 4 , -C(=O)NHR 4 , -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 , -NR 4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 , 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio, and arylamino.

[0481] Embodiment 17. The compound of Embodiment 16, or a salt, solvate, or stereoisomer thereof, wherein R 2a and R 2b are independently C1-C9 alkyl.

[0482] Embodiment 18. The compound of Embodiment 17, or a salt, solvate, or stereoisomer thereof, wherein R 2a and R 2b are methyl.

[0483] Embodiment 19. The compound of any one of Embodiments 1 to 5, or a salt, solvate, or stereoisomer thereof, having Formula (VI):

[0484]

[0485] wherein R 2a and R 2c are independently selected from the group consisting of halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C1-C8 alkylthio, C(=O)OR 4 , -OC(=O)R 4 , -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NHR 4 , -NR 4 R 5 , -OH, -SH, -SC(=O)R 4 , -SC(=O)SR 4 , -SC(=O)NHR 4 , -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 , -NR 4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 , 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio, and arylamino.

[0486] Embodiment 20. The compound of Embodiment 19, or a salt, solvate, or stereoisomer thereof, wherein R 2a and R 2c are independently C1-C9 alkyl.

[0487] Embodiment 21. The compound of Embodiment 20, or a salt, solvate, or stereoisomer thereof, wherein R 2a and R 2c are methyl.

[0488] Embodiment 22. The compound of any one of Embodiments 1 to 5, or a salt, solvate, or stereoisomer thereof, having Formula (VII):

[0489]

[0490] wherein R 2b and R 2c are independently selected from the group consisting of halogen, Ci-C9alkyl, Ci-C9haloalkyl, C3-C8cycloalkyl, Ci-C8alkoxy, Ci-C8alkylthio, C(=O)OR 4 , -OC(=O)R 4 , -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NHR 4 , -NR 4 R 5 , -OH, -SH, -SC(=O)R 4 , -SC(=O)SR 4 , -SC(=O)NHR 4 , -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 , -NR 4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 , 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio, and arylamino.

[0491] Embodiment 23. The compound of Embodiment 22, or a salt, solvate, or stereoisomer thereof, wherein R 2b and R 2c are independently Ci-C9alkyl.

[0492] Embodiment 24. The compound of Embodiment 23, or a salt, solvate, or stereoisomer thereof, wherein R 2b and R 2c are methyl.

[0493] Embodiment 25. The compound of any one of embodiments 1 to 5, or a salt, solvate, or stereoisomer thereof, wherein R 2a , R 2b , and R 2c are independently selected from the group consisting of halogen, C1-C9alkyl, C1-C6alkoxy, and C1-C6alkylthio.

[0494] Embodiment 26. The compound of any one of embodiments 1 to 25, or a salt, solvate, or stereoisomer thereof, wherein is a double bond.

[0495] Embodiment 27. The compound of any one of embodiments 1 to 25, or a salt, solvate, or stereoisomer thereof, wherein is a single bond.

[0496] Example

[0497] Example 1

[0498] Step 1 of synthesis of 8-methoxy-2,2,4-trimethyl-N-phenylquinolin-6(2H)-imine (Compound 7)

[0499]

[0500] To a 250-mL round bottom flask, equipped with a stir bar and a thermometer, was added 3-methoxydiphenylamine (11.8 g; 59.2 mmol) and glacial acetic acid (36 mL). The mixture was stirred under N2protection (outlet connected to a base trap containing about 250 mL of 1M NaOH). A 37% aqueous HC1 solution (18 mL; 217 mmol of HC1) was added portionwise over several minutes. The 3-methoxydiphenylamine dissolved upon addition of the aqueous HC1 solution. No exothermic phenomenon was observed. A light yellow solution was obtained. The flask was cooled with an ice water bath. Once the temperature reached 4-5 °C, a solution of sodium nitrite (4.169 g; 60.4 mmol) in distilled water (12 mL) was added gradually over a period of 17-18 minutes, so that the temperature remained below 10 °C. The resulting dark red mixture was stirred between 2 °C and 9 °C for 30 minutes, then the cooling bath was removed. The reaction mixture was stirred for 2 hours and 40 minutes without external cooling or heating (2-22 °C), whereby a dark red solid separated. Distilled water (80 mL) was added and the slurry was stirred for a few minutes. The solid was collected by suction filtration, then quickly rinsed with distilled water and EtOH (50 mL). Drying under vacuum at 40 °C for about 2 hours, then overnight at room temperature, afforded 7.8 g (57% of theory relative to 3-methoxydiphenylamine) of a dark red powder. An aliquot of this material was characterized by LC-MS / UV (260 nm). The crude material was engaged in the next step without further purification.

[0501] Step 2

[0502]

[0503] To a 500-mL flask, equipped with a stir bar and a thermometer, was added 3- methoxy-4-nitroso-N-phenylaniline (see Step 1; 7.8 g; 34.2 mmol) and EtOH (210 mL). The mixture was stirred under N2protection (some solids remained undissolved; a red slurry was obtained). Ammonium sulfate (9.05 g; 68.5 mmol) was added in one portion (no exotherm was observed), and the mixture was stirred at room temperature for about 1 h. The flask was cooled with a cold tap water bath. Sodium borohydride (3.31 g; 87.5 mmol) was added in portions over a period of 16 min, so that the temperature remained below 28 °C (foaming occurred). The reaction mixture was stirred with a water bath for 110 min, during which time the reaction mixture turned black. The water bath was removed. After about 10 min, distilled water (150 mL) was added slowly, and the mixture was stirred for a few minutes. The mixture was diluted with ethyl acetate (450 mL) in a separatory funnel containing distilled water (100 mL) and 1 M aqueous NaOH (100 mL). After shaking and decanting, the aqueous layer was discarded. The organic layer was washed with 1 M aqueous NaOH (100 mL) and brine (100 mL), dried over MgS04, filtered, and the volatiles were stripped under reduced pressure (rotary evaporator; water bath = 55 °C). The resulting black oily substance was dried on a rotary evaporator (55 °C; < 12 mbar) for 1 h. Crude yield = 6.2 g as a black gummy substance. The crude material was dissolved in toluene (10 mL). The resulting black solution was loaded onto a 71 mm diameter chromatography column previously prepared with silica gel 60 (8" height) and eluent (50% ethyl acetate in hexanes). The flask was rinsed with 50% ethyl acetate in hexanes (5-10 mL). The column was eluted with 50% ethyl acetate in hexanes. Fractions containing the desired product (TLC 50% ethyl acetate in hexanes; spots at Rf = 0.7) were collected (100 mL each), combined, and the volatiles were stripped under reduced pressure (rotary evaporator; water bath = 50 °C). The resulting black / purple viscous liquid was dried on a rotary evaporator (55 °C; < 2 mbar) for 15-30 min. Yield = 4.3 g (58% based on 3-methoxy-4-nitroso-N-phenylaniline) as a dark viscous substance.

[0504] Step 3

[0505]

[0506] To a 250-mL flask, equipped with a stir bar and a reflux condenser, was added 3- methoxy-N 1phenylbenzene-1,4-diamine (4.3 g; 20.1 mmol), acetone (8.9 mL; 120 mol) and zinc (II) trifluoromethanesulphonate (0.727 g; 2.00 mmol). The mixture was stirred and heated (oil bath = 62 °C) under N2protection for 40.5 h. It took about 2 h for the substrate to dissolve initially, then a dark homogenous solution was obtained. After cooling to room temperature, the obtained black liquid was loaded onto a 41 mm diameter column previously prepared with silica gel 60 (30 cm height) and eluent (20% ethyl acetate in hexane). The flask was rinsed with additional acetone (3-4 mL). The column was eluted with 20% ethyl acetate in hexane. Several fractions were collected (about 30 mL each) and characterized by silica gel TLC (20% ethyl acetate in hexane). The fractions containing the spot with Rf = 0.6 (desired product) were collected, combined and the volatiles were stripped under reduced pressure (rotavapor; water bath = 50 °C). The resulting powder was dried on the rotavapor (55 °C; < 3 mbar) for 20 min to give 8-methoxy-2,2,4-trimethyl-N-phenyl-1,2-dihydroquinolin-6-amine. Yield = 2.5 g (42% relative to 3-methoxy-N 1 phenylbenzene-1,4-diamine was 42% of the theoretical value), as an almost white crystalline powder.

[0507] Step 4

[0508]

[0509] A 20-mL vial, equipped with a stirring bar, was charged with 8-methoxy-2,2,4-trimethyl-N-phenyl-1,2-dihydroquinolin-6-amine (300 mg; 1.02 mmol) and acetonitrile (5.5 mL). The mixture was stirred. The substrate did not completely dissolve. A 10-15 wt% aqueous NaOCI solution (0.65 mL) was added. The reaction mixture was stirred for 35 min without external cooling or heating, whereby an orange solution was obtained. A 17 wt% aqueous sodium sulfite solution (1.0 mL; 1.35 mmol sulfite anion) was added to quench the excess hypochlorite. Ethyl acetate (about 10-11 mL) and anhydrous magnesium sulfate were added in sequence under vigorous stirring. The mixture was filtered by gravimetric method. The volatiles were stripped from the filtrate under reduced pressure (rotavapor; water bath = 50 °C) to give about 300 mg of compound 7 as a dark solid. The structure was identified by H NMR spectroscopy (as shown in Figure 1 1 ) and LC-MS (as shown in Figure 12). The purity was measured by LC-UV260 to be 94.0 area% (combined area of the two stereoisomers), as shown in Figure 13. The melting point of compound 7 was measured to be in the range of 150 °C to 185 °C. 1 H NMR spectroscopy (as Figure 1 shown in Figure 1 1 ) and LC-MS (as Figure 2 shown in Figure 12). The purity was measured by LC-UV260 to be 94.0 area% (combined area of the two stereoisomers), as Figure 2 shown in Figure 13. The melting point of compound 7 was measured to be in the range of 150 °C to 185 °C.

[0510] Example 2

[0511] Oxidation Induction Time (OIT) performance of compound 7

[0512] The oxidation induction time (OIT) of selected compounds of the present disclosure was evaluated. OIT was measured according to a procedure performed in a differential scanning calorimeter (DSC; TA Instruments, Q200). In this procedure, the sample is held in a cell and heated to a preselected temperature under a nitrogen atmosphere. Oxygen (O2) is then introduced into the cell, and the length of time before degradation begins is measured, as observed by the onset of an endothermic process in the DSC trace.

[0513] A 0.5 wt% of a compound of the present disclosure, Compound N 1 - (4-methylpentan-2-yl)-N 4 - phenylphenyl-1,4-diamine (6PPD) or no antioxidant (blank) were mixed with polyisoprene and isothermally heated at 150 °C and / or 160 °C under O2. The OIT in minutes is shown in Table 3. As shown by the data in Table 3, the compounds of the present disclosure exhibit antioxidant activity.

[0514] Table 3

[0515] Material OIT at 150°C (min) OIT at 160°C (min) Blank 2.0 1.2 Compound 7 58.5 24.6 6PPD 39.9 21.9

[0516] Having now fully described the methods, compounds, and compositions herein, it will be understood by those of ordinary skill in the art that the same can be performed within wide and equivalent ranges of conditions, formulations and other parameters without affecting the scope of the methods, compounds and compositions provided herein or any embodiments thereof. All patents, patent applications, and publications cited herein are fully incorporated by reference herein in their entirety.

Claims

1. A compound of Formula (I): Formula (I) or a salt, solvate, or stereoisomer thereof, wherein: with the proviso that the compound of Formula (I) is not: is a single or double bond; R 1 optionally substituted C1-C6alkyl, -CHR 12 optionally substituted C1-C6alkyl, -CHR 1a R 1b , C3-C6cycloalkyl, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl; R 1a is selected from the group consisting of optionally substituted phenyl, C3-C6cycloalkyl and optionally substituted 5- or 6-membered heteroaryl; R 1b selected from the group consisting of hydrogen and C1-C9alkyl; R 2a , R 2b , and R 2c are independently selected from the group consisting of hydrogen, halogen, C1-C9alkyl, C1-C9haloalkyl, C3-C8cycloalkyl, C1-C8alkoxy, C1-C8alkylthio, C(=O)OR 4 , -OC(=O)R 4 , -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NHR 4 , -NR 4 R 5 , -OH, -SH, -SC(=O)R 4 , -SC(=O)SR 4 , -SC(=O)NHR 4 , -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 , -NR 4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 , 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio, and arylamino; or R 2a and R 2c together with the two carbon atoms to which they are attached form an optionally substituted C3-C6cycloalkyl, an optionally substituted 4- to 6-membered heterocyclyl, an optionally substituted 4- to 6-membered aryl, or an optionally substituted 4- to 6-membered heteroaryl; and R 2b is selected from the group consisting of hydrogen, halogen, C1-C9alkyl, C1-C9haloalkyl, optionally substituted C3-C8cycloalkyl, -OH, C1-C8alkoxy, -SH, C1-C8alkylthio, -C(=O)OR 4 , -OC(=O)R 4 , -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NHR 4 , -NR 4 R 5 , -SC(=O)R 4 , -SC(=O)SR 4 , -SC(=O)NHR 4 , -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 , -NR 4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 , optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio and arylamino; R 3a is selected from the group consisting of hydrogen, halogen, Ci-C9alkyl, optionally substituted phenyl, -C(=0)OR 4 , -C(=0)NR 4 R 5 , -C(=0)SR 4 , -CH2OR 4 , -CH2OC(=0)R 4 and and R 3b is selected from the group consisting of hydrogen, halogen, Ci-C9alkyl, and optionally substituted phenyl; or R 3a and R 3b together with the carbon atom to which they are attached form a C3-C 12 cycloalkyl; R 3c is selected from the group consisting of hydrogen, halogen, Ci-C9alkyl, optionally substituted phenyl, -C(=0)OR 4 , -C(=0)NR 4 R 5 , -C(=0)SR 4 , -CH2OR 4 , -CH2OC(=0)R 4 and and R 3d selected from the group consisting of hydrogen, halogen, Ci-C9alkyl, and optionally substituted phenyl; or R 3c and R 3d together with the two carbon atoms to which they are attached form a C3-C 12 cycloalkyl; R 4 is independently at each occurrence selected from the group consisting of hydrogen and C1-C9alkyl; and R 5 is independently at each occurrence selected from the group consisting of hydrogen and C1-C9alkyl; R 6a , R 6b , R 6c and R 6d are independently at each occurrence selected from the group consisting of hydrogen, C1-C 12 alkyl and optionally substituted phenyl; Z is independently selected, at each occurrence, from the group consisting of -0-, -S-, and -NR 7 - the group consisting of: R 7 is independently at each occurrence selected from the group consisting of hydrogen and C1-C6alkyl, 7. The compound of any one of claims 1 to 5 or a salt, solvate, or stereoisomer thereof, of Formula (II): Formula (II).

2. The compound of claim 1 or a salt, solvate, or stereoisomer thereof, wherein R 3a , R 3b , and R 3c are independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, pentyl, hexyl, heptyl, octyl, and nonyl.

3. The compound of claim 2, or a salt, solvate, or stereoisomer thereof, wherein R 3a , R 3b , and R 3c are methyl.

4. The compound of any one of claims 1 to 3, or a salt, solvate, or stereoisomer thereof, wherein R 1 is optionally substituted phenyl.

5. The compound of any one of claims 1 to 3, or a salt, solvate, or stereoisomer thereof, wherein R 1 is C1-C 12 alkyl.

6. The compound of any one of claims 1 to 5, wherein R 2a , R 2b , and R 2c are hydrogen.

10. The compound of any one of claims 1 to 5 or a salt, solvate, or stereoisomer thereof, of Formula (III): Formula (III). wherein R 2a is selected from the group consisting of halogen, Ci-C9alkyl, Ci-C9haloalkyl, C3-C8cycloalkyl, Ci-C8alkoxy, Ci-C8alkylthio, C(=O)OR 4 , -OC(=O)R 4 , -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NHR 4 , -NR 4 R 5 , -OH, -SH, -SC(=O)R 4 , -SC(=O)SR 4 , -SC(=O)NHR 4 , -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 , -NR 4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 , 4- to 6-membered heterocyclyl, optionally substituted phenyl and optionally substituted 5- or 6-membered heteroaryl.

8. The compound of claim 7, or a salt, solvate, or stereoisomer thereof, wherein R 2a is Ci-C9alkyl.

9. The compound of claim 8, or a salt, solvate, or stereoisomer thereof, wherein R 2a is methyl.

13. The compound of any one of claims 1 to 5 or a salt, solvate, or stereoisomer thereof, of Formula (IV): Formula (IV). wherein R 2b is selected from the group consisting of halogen, Ci-C9alkyl, Ci-C9haloalkyl, C3-C8cycloalkyl, Ci-C8alkoxy, Ci-C8alkylthio, C(=O)OR 4 , -OC(=O)R 4 , -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NHR 4 , -NR 4 R 5 , -OH, -SH, -SC(=O)R 4 , -SC(=O)SR 4 , -SC(=O)NHR 4 , -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 , -NR 4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 , 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio and arylamino.

11. The compound of claim 10, or a salt, solvate, or stereoisomer thereof, wherein R 2b is Ci-C9alkyl.

12. The compound of claim 11, or a salt, solvate, or stereoisomer thereof, wherein R 2b is methyl.

16. The compound of any one of claims 1 to 5 or a salt, solvate, or stereoisomer thereof, of Formula (V): Formula (V). wherein R 2c is selected from the group consisting of halogen, Ci-C9alkyl, Ci-C9haloalkyl, C3-C8cycloalkyl, Ci-C8alkoxy, Ci-C8alkylthio, C(=O)OR 4 , -OC(=O)R 4 , -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NHR 4 , -NR 4 R 5 , -OH, -SH, -SC(=O)R 4 , -SC(=O)SR 4 , -SC(=O)NHR 4 , -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 , -NR 4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 , 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio and arylamino.

14. The compound of claim 13, or a salt, solvate, or stereoisomer thereof, wherein R 2c is Ci-C9alkyl.

15. The compound of claim 14, or a salt, solvate, or stereoisomer thereof, wherein R 2c is methyl.

19. The compound of any one of claims 1 to 5 or a salt, solvate, or stereoisomer thereof, of Formula (VI): Formula (VI). wherein R 2a and R 2b are independently selected from the group consisting of halogen, Ci-C9alkyl, Ci-C9haloalkyl, C3-C8cycloalkyl, Ci-C8alkoxy, Ci-C8alkylthio, C(=O)OR 4 , -OC(=O)R 4 , -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NHR 4 , -NR 4 R 5 , -OH, -SH, -SC(=O)R 4 , -SC(=O)SR 4 , -SC(=O)NHR 4 , -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 , -NR 4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 , 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio and arylamino.

17. The compound of claim 16, or a salt, solvate, or stereoisomer thereof, wherein R 2a and R 2b are independently C1-C9 alkyl.

18. The compound of claim 17, or a salt, solvate, or stereoisomer thereof, wherein R 2a and R 2b are methyl.

22. The compound of any one of claims 1 to 5 or a salt, solvate, or stereoisomer thereof, of Formula (VII): Formula (VII). wherein R 2a and R 2c are independently selected from the group consisting of halogen, Ci-C9alkyl, Ci-C9haloalkyl, C3-C8cycloalkyl, Ci-C8alkoxy, Ci-C8alkylthio, C(=O)OR 4 , -OC(=O)R 4 , -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NHR 4 , -NR 4 R 5 , -OH, -SH, -SC(=O)R 4 , -SC(=O)SR 4 , -SC(=O)NHR 4 , -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 , -NR 4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 , 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio and arylamino.

20. The compound of claim 19, or a salt, solvate, or stereoisomer thereof, wherein R 2a and R 2c are independently C1-C9 alkyl.

21. The compound of claim 20, or a salt, solvate, or stereoisomer thereof, wherein R 2a and R 2c are methyl.

33. The compound of claim 1 or a salt, solvate, or stereoisomer thereof, selected from any one or more of the compounds of Table 1A. wherein R 2b and R 2c are independently selected from the group consisting of halogen, Ci-C9alkyl, Ci-C9haloalkyl, C3-C8cycloalkyl, Ci-C8alkoxy, Ci-C8alkylthio, C(=O)OR 4 , -OC(=O)R 4 , -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NHR 4 , -NR 4 R 5 , -OH, -SH, -SC(=O)R 4 , -SC(=O)SR 4 , -SC(=O)NHR 4 , -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 , -NR 4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 , 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio and arylamino.

23. The compound of claim 22, or a salt, solvate, or stereoisomer thereof, wherein R 2b and R 2c are independently C1-C9 alkyl.

24. The compound of claim 23, or a salt, solvate, or stereoisomer thereof, wherein R 2b and R 2c are methyl.

25. The compound of any one of claims 1 to 5 or a salt, solvate, or stereoisomer thereof, wherein R 2a , R 2b , and R 2c are independently selected from the group consisting of halogen, Ci-C9alkyl, Ci-C6alkoxy, and Ci-C6alkylthio.

26. The compound of any one of claims 1 to 25, or a salt, solvate, or stereoisomer thereof, wherein is a double bond.

27. The compound of any one of claims 1 to 25, or a salt, solvate, or stereoisomer thereof, wherein is a single bond.

28. The compound of claim 1 or a salt, solvate, or stereoisomer thereof, wherein R 3a and R 3c are -C(=O)OR 4 .

29. The compound of claim 28, or a salt, solvate, or stereoisomer thereof, wherein each R 4 is independently hydrogen or C1-C9 alkyl.

30. The compound of claim 29, or a salt, solvate, or stereoisomer thereof, wherein each R 4 is ethyl.

31. The compound of any one of claims 28 to 30, or a salt, solvate, or stereoisomer thereof, wherein R 3b is Ci-C9alkyl.

32. The compound of claim 31, or a salt, solvate, or stereoisomer thereof, wherein R 3b is methyl.

34. A compound of Formula (VIII): Formula (VIII) or a salt, solvate, or stereoisomer thereof, wherein:

35. The compound of claim 34 or a salt, solvate, or stereoisomer thereof, of Formula (IX): Formula (IX).

36. The compound of claim 34 or a salt, solvate, or stereoisomer thereof, of Formula (X): Formula (X). each is independently a single or double bond; R 8a and R 8b are independently selected from the group consisting of hydrogen, halogen, Ci-C9alkyl, Ci-C9haloalkyl, C3-C8cycloalkyl, Ci-C8alkoxy, Ci-C8alkylthio, C(=O)OR 4 , -OC(=O)R 4 , -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NR 4 R 5 , -OH, -SH, -SC(=O)R 4 , -SC(=O)SR 4 , -SC(=O)NR 4 R 5 , -NR 4 C(=O)SR 5 , -NR 4 C(=S)SR 5 , 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, aryloxy, arylthio and arylamino; R 9a selected from the group consisting of hydrogen, halogen, Ci-C9alkyl, optionally substituted phenyl, -C(=0)OR 4 , -C(=0)NR 4 R 5 , -C(=0)SR 4 , -CH2OR 4 , -CH2OC(=0)R 4 and and R 9b selected from the group consisting of hydrogen, halogen, Ci-C9alkyl, and optionally substituted phenyl; or R 9a and R 9b together with the carbon atom to which they are attached form a C3-C 12 cycloalkyl; R 9c selected from the group consisting of hydrogen, halogen, Ci-C9alkyl, optionally substituted phenyl, -C(=0)OR 4 , -C(=0)NR 4 R 5 , -C(=0)SR 4 , -CH2OR 4 , -CH2OC(=0)R 4 and and R 9d selected from the group consisting of hydrogen, halogen, Ci-C9alkyl, and optionally substituted phenyl; or R 9c and R 9d together with the two carbon atoms to which they are attached form a C3-C 12 cycloalkyl; R 10a selected from the group consisting of hydrogen, halogen, C1-C9alkyl, optionally substituted phenyl, -C(=O)OR 4 , -C(=O)NR 4 R 5 , -C(=O)SR 4 , -CH2OR 4 , -CH2OC(=O)R 4 and and R 10b is selected from the group consisting of hydrogen, halogen, Ci-C9alkyl, and optionally substituted phenyl; or R 10a and R 10b together with the carbon atom to which they are attached form a C3-C 12 cycloalkyl; R 10c is selected from the group consisting of hydrogen, halogen, Ci-C9alkyl, optionally substituted phenyl, -C(=0)OR 4 , -C(=0)NR 4 R 5 , -C(=0)SR 4 , -CH2OR 4 , -CH2OC(=0)R 4 and and R 10d is selected from the group consisting of hydrogen, halogen, Ci-C9alkyl, and optionally substituted phenyl; or R 10c and R 10d together with the two carbon atoms to which they are attached form a C3-C 12 cycloalkyl; Z is independently selected, at each occurrence, from the group consisting of -0-, -S-, and -NR 7 - the group consisting of R 4 is independently at each occurrence selected from the group consisting of hydrogen, C1-C9alkyl, C3-C6cycloalkyl, and optionally substituted phenyl; and R 5 is independently at each occurrence selected from the group consisting of hydrogen, C1-C9alkyl, C3-C6cycloalkyl, and optionally substituted phenyl; R 6a , R 6b , R 6c and R 6d are independently at each occurrence selected from the group consisting of hydrogen, C1-C 12 alkyl and optionally substituted phenyl; and R 7 is independently at each occurrence selected from the group consisting of hydrogen and C1-C6alkyl.

63. The compound of claim 34 or a salt, solvate, or stereoisomer thereof, selected from any one or more of the compounds of Table 1B.

64. A composition comprising:

37. The compound of any one of claims 34 to 36, or a salt, solvate, or stereoisomer thereof, wherein R 8a and R 8b are hydrogen.

38. The compound of any one of claims 34 to 37, or a salt, solvate, or stereoisomer thereof, wherein R 9a , R 9b , and R 9c are independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, pentyl, hexyl, heptyl, octyl, and nonyl.

39. The compound of claim 38, or a salt, solvate, or stereoisomer thereof, wherein R 9a , R 9b , and R 9c are methyl, ethyl, or isobutyl.

40. The compound of claim 39, or a salt, solvate, or stereoisomer thereof, wherein R 9a and R 9c are methyl.

41. The compound of claim 39, or a salt, solvate, or stereoisomer thereof, wherein R 9a and R 9c are ethyl.

42. The compound of claim 39, or a salt, solvate, or stereoisomer thereof, wherein R 9a and R 9c is isobutyl.

43. The compound of any one of claims 34 to 37, or a salt, solvate, or stereoisomer thereof, wherein R 9a and R 9c are -C(=O)OR 4 , -C(=O)NR 4 R 5 , -C(=O)SR 4 , -CH2OR 4 , -CH2OC(=O)R 4 or 44. The compound of claim 43, or a salt, solvate, or stereoisomer thereof, wherein R 9a and R 9c are -C(=O)OR 4 .

45. The compound of claim 44, or a salt, solvate, or stereoisomer thereof, wherein each R 4 is hydrogen, methyl, or ethyl.

46. The compound of claim 45, or a salt, solvate, or stereoisomer thereof, wherein each R 4 is ethyl.

47. The compound of any one of claims 43 to 46, or a salt, solvate, or stereoisomer thereof, wherein R 9b is methyl.

48. The compound of any one of claims 34 to 47, or a salt, solvate, or stereoisomer thereof, wherein R 9d is hydrogen.

49. The compound of any one of claims 34 to 48, or a salt, solvate, or stereoisomer thereof, wherein R 10a , R 10b , and R 10c are independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, pentyl, hexyl, heptyl, octyl, and nonyl.

50. The compound of claim 49, or a salt, solvate, or stereoisomer thereof, wherein R 10a , R 10b , and R 10c are methyl, ethyl, or isobutyl.

51. The compound of claim 50, or a salt, solvate, or stereoisomer thereof, wherein R 10a and R 10c are methyl.

52. The compound of claim 51, or a salt, solvate, or stereoisomer thereof, wherein R 10a and R 10c are ethyl.

53. The compound of claim 51 or a salt, solvate, or stereoisomer thereof, wherein R 10a and R 10c is isobutyl.

54. The compound of any one of claims 34 to 53, or a salt, solvate, or stereoisomer thereof, wherein R 10a and R 10c are -C(=O)OR 4 , -C(=O)NR 4 R 5 , -C(=O)SR 4 , -CH2OR 4 , -CH2OC(=O)R 4 or 55. The compound of claim 54, or a salt, solvate, or stereoisomer thereof, wherein R 10a and R 10c are -C(=O)OR 4 .

56. The compound of claim 55, or a salt, solvate, or stereoisomer thereof, wherein each R 4 is hydrogen, methyl, or ethyl.

57. The compound of any one of claims 34 to 56, or a salt, solvate, or stereoisomer thereof, wherein R 10b is methyl.

58. The compound of any one of claims 34 to 57, or a salt, solvate, or stereoisomer thereof, wherein R 10d is hydrogen.

59. The compound of any one of claims 34 to 58, or a salt, solvate, or stereoisomer thereof, wherein R 9a and R 10a are the same.

60. The compound of any one of claims 34 to 59, or a salt, solvate, or stereoisomer thereof, wherein R 9b and R 10b are the same.

61. The compound of any one of claims 34 to 60, or a salt, solvate, or stereoisomer thereof, wherein R 9c and R 10c are the same.

62. The compound of any one of claims 34 to 61, or a salt, solvate, or stereoisomer thereof, wherein R 9d and R 10d are the same. (i) a compound of any one of claims 1 to 63; and (ii) one or more elastomers; or (iii) one or more fillers; or (iv) one or more rubber chemicals; or (v) one or more plasticizers; or (vi) one or more additional antidegradants; or (vii) a combination of one or more elastomers, one or more fillers, one or more rubber chemicals, one or more plasticizers, and / or one or more additional antidegradants.

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

66. The composition of claim 64 or 65, wherein the composition comprises about 0.1 weight / weight % to about 10 weight / weight % of the compound.

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

68. The composition of claim 67, wherein the one or more elastomers comprise about 5 weight / weight % to about 80 weight / weight % of natural rubber (NR).

69. The composition of claim 67 or 68, wherein the natural rubber comprises rubber derived from an alternative rubber plant. ​ ​ 70. The composition of claim 69, wherein the alternative rubber plant is Parthenium argentatum (Guayule) or Taraxacum koksaghy (Russian dandelion).

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

72. The composition of claim 71, wherein the synthetic rubber comprises an unsaturated rubber, a saturated rubber, a rubber with fluorine and fluoroalkyl or fluoroalkoxy substituent groups on the polymer chain (FKM), a silicone rubber (Q), or a blend thereof.

73. The composition of claim 72, wherein the unsaturated rubber comprises polyisoprene rubber (IR), butyl rubber (IIR), polybutadiene rubber (BR), styrene butadiene rubber (SBR), nitrile rubber (NBR), chloroprene rubber (CR), ethylene propylene termonomer rubber (EPDM), or a blend thereof.

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

75. The composition of claim 74, wherein the one or more elastomers comprise about 5% to about 80% by weight / weight of styrene butadiene rubber (SBR).

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

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

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

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

80. The composition of any one of claims 72 to 79, wherein the saturated rubber comprises acrylic rubber (ACM), chlorinated polyethylene (CM), chlorosulfonated polyethylene (CSM), polychloromethyl oxirane (CO), ethylene-ethyl acrylate copolymer (EAM), epichlorohydrin rubber (ECO), ethylene propylene rubber (EPM), ethylene vinyl acetate copolymer (EVM), or a blend thereof.

81. The composition of any one of claims 64 to 80, wherein the one or more elastomers further comprise reclaimed rubber.

82. The composition of any one of claims 64 to 81, wherein the composition comprises about 0.1 phr to about 10 phr of the compound.

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

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

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

86. The composition of claim 85, wherein the composition comprises about 15% to about 85% by weight by weight of the compound and about 15% to about 85% by weight by weight of the one or more fillers.

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

88. The composition of any one of claims 85 to 87, wherein the one or more fillers comprise carbon black, silica, kaolin, calcium silicate, talc, carbon nanotubes (CNTs), carbon fibers (HCFs), graphite, graphene, aluminosilicates, starch, fibers, or combinations thereof.

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

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

91. The composition of any one of claims 85 to 90, wherein the one or more fillers comprise carbon black.

92. The composition of any one of claims 64 to 63, wherein the composition comprises one or more rubber chemicals.

93. The composition of claim 92, wherein the composition comprises about 15% to about 85% by weight by weight of the compound and about 15% to about 85% by weight by weight of one or more rubber chemicals.

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

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

96. The composition of any one of claims 92 to 95, wherein the one or more rubber chemicals comprise one or more vulcanizing agents, one or more accelerators, one or more activators, one or more prevulcanization inhibitors, or combinations thereof.

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

98. The composition of claim 97, wherein one or more vulcanizing agents comprise sulfur, peroxides, resins, or combinations thereof.

99. The composition of claim 98, wherein the sulfur is octasulfur (S8), cyclododecasulfur (S 12 ), polymeric sulfur, or a combination thereof.

100. The composition of claim 98, wherein the peroxides are 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), 4,4-di(tert- butylperoxy)butyl valerate (VAL), 1,1-di(tert-butylperoxy)-3,3,5-trimethylcyclohexane (TMC), or combinations thereof.

101. The composition of claim 98, wherein the resins are adhesive resins.

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

103. The composition of claim 102, wherein the one or more accelerators comprise guanidine, thiazole, sulfenamide, dithiocarbamate, xanthate, thiophosphate, or a combination thereof.

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

105. The composition of claim 103, wherein the thiazole comprises 2-mercaptobenzothiazole (MBT), zinc 2-mercaptobenzothiazole (ZMBT), mercaptobenzothiazole disulfide (MBTS), N-tert-butyl-2-benzothiazyl sulfenamide (TBSI), or a combination thereof.

106. The composition of claim 103, wherein the sulfenamide comprises N-tert-butyl-2- benzothiazyl sulfenamide (TBBS), N-cyclohexylbenzothiazole-2-sulfenamide (CBS), dicyclohexyl-2-benzothiazyl sulfenamide (DCBS), N-oxydiethylenebenzothiazyl sulfenamide (OBTS), N-oxydiethylene thiocarbamoyl-N'-oxydiethylene sulfenamide (OTOS), thiocarbamyl sulfenamide, or a combination thereof.

107. The composition of claim 103, wherein the dithiocarbamate is dimethyl dithiocarbamic acid disulfide peroxide anhydride (thiram), dipentamethylene dithiocarbamate tetrasulfide (DPIT), tetrabenzyl dithiocarbamate disulfide (TBzTD), tetraethyl dithiocarbamate disulfide (TETD), tetramethyl dithiocarbamate disulfide (TMTD), tetramethyl dithiocarbamate monosulfide (TMTM), or a combination thereof.

108. The composition of claim 103, wherein the dithiocarbamate comprises zinc dimethyl dithiocarbamate (ZDMC), zinc diethyl dithiocarbamate (ZDEC), zinc dibutyl dithiocarbamate (ZDBC), nickel dibutyl dithiocarbamate (NDBC), sodium dibenzyl dithiocarbamate (SBEC), sodium diethyl dithiocarbamate (SDEC), tellurium diethyl dithiocarbamate (TDEC), zinc dibenzyl dithiocarbamate (ZEBC), or a combination thereof.

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

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

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

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

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

114. The composition of any one of claims 96 to 113, wherein the one or more rubber chemicals comprise one or more presulfurization inhibitors.

115. The composition of claim 114, wherein one or more presulfurization inhibitors comprise N-(cyclohexylthio)phthalimide (CTP), benzoic anhydride, salicylic anhydride, phthalic anhydride, or a combination thereof.

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

117. The composition of claim 116, wherein the composition comprises about 15% to about 85% by weight by weight of the compound and about 15% to about 85% by weight by weight of one or more plasticizers.

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

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

120. The composition of any one of claims 116 to 119, wherein the one or more plasticizers comprise mineral oil, organic ester, resin, wax, ester plasticizer, oil of natural origin, or a combination thereof.

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

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

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

124. The composition of claim 123, wherein the composition comprises about 15% to about 85% by weight by weight of the compound and about 15% to about 85% by weight by weight of the one or more additional anti-degradation agents.

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

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

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

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

129. The composition of any one of claims 123 to 128, wherein the one or more additional anti-degradation agents are antioxidants.

130. The composition of any one of claims 123 to 128, wherein the one or more additional anti-degradation agents are antiozonants.

131. The composition of any one of claims 123 to 130, wherein the one or more additional anti-degradation agents is a p-phenylenediamine (PPD), a trimethyldihydroquinoline (TMQ), a phenol, an alkylated diphenylamine (DPA), or a diphenylamine-ketone condensate.

132. The composition of claim 131, wherein the PPD is N 1 - (4-methylpentan-2-yl)-N 4 - phenylphen-1,4-diamine (6PPD), N-(1,4-dimethylpentyl)-N'-phenyl-p- phenylenediamine (7PPD), N-sec-octyl-N'-phenyl-p-phenylenediamine (8PPD), N 1 - phenyl-N 4 - (prop-2-yl)benzene-1,4-diamine (IPPD), N,N'-di-sec-butyl-p-phenylenediamine (44PD), N,N'-bis(1,3-dimethylbutyl)-p-phenylenediamine (66PD), N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine (77PD), or N-N'-dioctyl-p-phenylenediamine (88PD).

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

134. The composition of claim 131, wherein the TMQ is 2,2,4-trimethyl- 1,2-dihydroquinoline or an oligomer or polymer thereof.

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

136. A method for making the composition of claim 135, the method comprising mixing the compound with the one or more carriers.

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

138. A vulcanized elastomeric article prepared using the composition of any one of claims 104 to 135.

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

140. The vulcanized elastomeric article of claim 139, wherein the tire is a passenger vehicle tire, a light truck tire, a heavy truck or bus tire, a motorcycle tire, an agricultural tire, a bulldozer tire, an aircraft tire, or a racing tire.

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

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

143. The vulcanized elastomeric article of claim 136 or 137, wherein the vulcanized elastomeric article is a rubber overshoe, a weather strip, an acoustical tile, an air spring, a bellows, a diaphragm, a tactile sensor, a cushion pad, a hose, a conveyor belt, or a flooring material.

144. A vehicle comprising the vulcanized elastomeric article of any one of claims 137 to 143.

145. A method for making a vulcanized elastomeric article, the method comprising: (a) forming the composition of any one of claims 65 to 134 into a shaped form; and (b) vulcanizing the shaped form to provide a vulcanized elastomeric article.

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

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

148. The method of any one of claims 145 to 147, wherein the vulcanized elastomeric article is a tire. ​ 149. The method of claim 148, wherein the tire is a passenger car tire, a light truck tire, a heavy truck or bus tire, a motorcycle tire, an agricultural tire, a bulldozer tire, an aircraft tire, or a racing tire.

150. The method of any one of claims 145 to 149, wherein the vulcanized elastomeric article is a component of a tire.

151. The method of claim 150, wherein the component is a bead, a belt, a carcass ply, an inner liner, a sidewall, a sub-tread, or a tread.

152. The method of any one of claims 150 to 157, wherein the vulcanized elastomeric article is a rubber overshoe, a weather strip, an acoustical panel, an air spring, a bellows, a diaphragm, a tactile sensor, a shock pad, a hose, a conveyor belt, or a flooring material.

153. A lubricant composition comprising a lubricant and a compound of any one of claims 1 to 63.

154. A combustible fuel composition comprising a combustible fuel and a compound of any one of claims 1 to 63.

155. A fuel additive composition comprising a fuel additive and a compound of any one of claims 1 to 63.

156. A method for retreading a tire, the method comprising: (a) applying a composition of any one of claims 64 to 135 to a tire; (b) disposing a pre-vulcanized tread around the tire; (c) disposing a curing envelope around the tire; and (d) vulcanizing the tire.

157. A kit comprising a composition of any one of claims 64 to 135 and instructions for using the composition in a vulcanizable elastomer composition.

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

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