Compositions comprising 2, 2, 4-trimethyl-n-phenyl-1, 2-dihydroquinoline-6-amine

Abstract

The present disclosure provides compounds and compositions having anti-degradation agent properties, such as anti-ozonant, antioxidant and / or anti-fatigue agent properties, which are useful additives to vulcanized rubber articles. In some embodiments, the composition comprises a 2, 2, 4-trimethyl-N-phenyl-1, 2-dihydroquinoline-6-amine, and a method for preparing the same.

Description

TECHNICAL FIELD

[0001] The present disclosure provides compounds and compositions having anti-degradation, e.g., anti-ozone, antioxidant, and / or anti-fatigue, properties that are useful additives to vulcanized rubber articles. In some embodiments, the compositions comprise 2,2,4-trimethyl-N-phenyl-1,2-dihydroquinolin-6-amine. BACKGROUND

[0002] Many materials, such as plastics, elastomers, elastomeric products (tires, belts, hoses, bushings, mounts, vibration isolators, etc.), lubricants, and petroleum products (such as hydraulic oils, oils, fuels, and oil / fuel additives for automotive and aviation applications) are susceptible to degradation upon prolonged exposure to light, heat, oxygen, ozone, repeated mechanical action, and the like. Accordingly, compounds and compositions that exhibit efficacy as anti-degradation agents are well known in the art. For example, U.S. Patent No. 8,987,515 discloses an aromatic polyamine that can be used to inhibit oxidative degradation, particularly in lubricant compositions. U.S. Patent Application Publication No. 2014 / 0316163 discloses antioxidant macromolecules that are said to have improved solubility in a number of commercially available oils and lubricants.

[0003] Anti-degradation agents that can be used to manufacture articles formed from elastomers, plastics, and the like require very specific combinations 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 long periods of time associated with the use of the article, particularly at the exposed surfaces of the article where degradation by environmental factors such as light, oxygen, and ozone primarily occurs. As important as it is to protect surface-exposed components, it is also critical to protect the embedded components of a composite material from oxidative aging and repeated mechanical action. Anti-degradation agents must achieve these results while not negatively impacting the efficacy or desired properties of other additives in the final article. Additionally, anti-degradation agents that provide or improve mechanical fatigue life after the article has been put into service, oxidatively aged, or exposed to ozone are of high value because they would fundamentally improve the useful mechanical service life of the article. Accordingly, elastomeric articles that experience repeated mechanical flexing, elongation, or compression during use would benefit greatly from this discovery.

[0004] Articles made from general-purpose elastomers such as natural rubber (particularly tires) are particularly susceptible to degradation by both oxygen and ozone. As discussed in U.S. Patent No. 2,905,654, the effects of oxygen degradation on rubber differ from those of ozone degradation; however, both effects can be detrimental to tire performance, appearance, and expected life. Fatigue and crack propagation are also of particular concern, especially for the steel belt edge areas and tire sidewalls (whether inflated, partially inflated, or uninflated), which are subjected to significant stress and tensile forces during bending, and this continues throughout the tire's lifespan. U.S. Patent No. 8,833,417 describes an antioxidant system that is claimed to provide greater long-term resistance to fatigue and crack propagation than known antioxidants discussed below.

[0005] Materials with anti-degradation properties are well known in the art for their use in tire applications and are commercially available. For example, N,N'-disubstituted p-phenylenediamines (such as those using Santoflex) TM Those sold under trademarks are generally favored by many tire manufacturers. EP 3147321 A1 discloses rubber compositions, tires, amine compounds, and anti-aging agents, and particularly rubber compositions allegedly suitable for tread or sidewall rubber of tires. U.S. Patent No. 3,362,930 discloses 6-anilino-2,2,4-trimethyl-1,2-dihydroquinoline and its use as an anti-ozone agent in rubber compositions. U.S. Patent No. 5,117,063 discloses a method for preparing 4-aminodiphenylamine (“4-ADPA”), and 4-ADPA can be used to prepare 6-anilino-2,2,4-trimethyl-1,2-dihydroquinoline. There is a need for compositions containing 6-anilino-2,2,4-trimethyl-1,2-dihydroquinoline (also known as 2,2,4-trimethyl-N-phenyl-1,2-dihydroquinoline-6-amine) and other anti-degradation agents for use in vulcanized rubber articles. Summary of the Invention

[0006] This disclosure provides compounds and compositions that can be used as anti-degradation agents (e.g., anti-ozone agents and / or antioxidants) and / or as additives in vulcanized rubber products, lubricants, or combustible fuels.

[0007] On the one hand, this disclosure provides a compound having formula (I):

[0008]

[0009] or its salts or solvates, wherein Indicates a single bond or a double bond.

[0010] On the other hand, this disclosure provides a compound having formula (II):

[0011]

[0012] or a salt or solvate thereof, wherein represents a single or double bond.

[0013] In another aspect, the present disclosure provides a compound of Formula (III):

[0014]

[0015] or a salt or solvate thereof, wherein represents a single or double bond.

[0016] In another aspect, the present disclosure provides a compound (21):

[0017]

[0018] or a salt or solvate thereof.

[0019] In another aspect, the present disclosure provides a compound (22):

[0020]

[0021] or a salt or solvate thereof.

[0022] In another aspect, the present disclosure provides a compound (23):

[0023]

[0024] or a salt or solvate thereof.

[0025] In another aspect, the present disclosure provides a compound (24):

[0026]

[0027] or a salt or solvate thereof.

[0028] In another embodiment, the present disclosure provides a compound (25):

[0029]

[0030] or a salt or solvate thereof.

[0031] In another aspect, the present disclosure provides a composition comprising a compound of Formula (IV):

[0032]

[0033] or a salt or solvate thereof, wherein represents a single or double bond.

[0034] In another aspect, the present disclosure provides a method for preparing a composition comprising Formula (IV), or a salt or solvate thereof, the method comprising reacting 4- aminodiphenylamine with acetone, 2,2-dimethoxypropane, or isopropylidene acetone in the presence of a strong acid (e.g., hydrochloric acid).

[0035] Additional embodiments and advantages of the present disclosure will be set forth in part in the description that follows, and will in part be apparent 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 particularly pointed out in the appended claims.

[0036] It is to be understood that both the foregoing summary of the application and the following detailed description are exemplary and explanatory only and are not restrictive of the application as claimed. BRIEF DESCRIPTION OF DRAWINGS

[0037] Figure 1 is a high performance liquid chromatography (HPLC) chromatogram of a representative composition of the present disclosure, which has been annotated to include peak positions of certain compounds of the present disclosure.

[0038] Figure 2 is two chromatograms demonstrating chromatographic detection of compound (2) in a mixture with compound (10) using Method 3 (top) and a chromatogram of authentic (2) (bottom).

[0039] Figure 3 is two chromatograms demonstrating chromatographic detection of compound (21) in a mixture with compound (10) using Method 3 (top) and a chromatogram of authentic (21) (bottom).

[0040] Figure 4 is two chromatograms demonstrating chromatographic detection of compound (23) in a mixture with compound (10) using Method 3 (top) and a chromatogram of authentic (23) (bottom).

[0041] Figure 5 is two chromatograms demonstrating chromatographic detection of compound (25) in a mixture with compound (10) using Method 3 (top) and a chromatogram of authentic (25) (bottom).

[0042] Figure 6 is two chromatograms demonstrating chromatographic detection of compound (21) in a mixture with compound (10) using Method 2 (top) and a chromatogram of authentic (21) (bottom).

[0043] Figure 7are two chromatograms showing the chromatographic detection of compound (25) in a mixture with compound (10) using method 2 (top) and the chromatogram of authentic (25) (bottom).

[0044] Figure 8 is the NMR spectrum of compound (4).

[0045] Figure 9 is the HPLC chromatogram of compound (4).

[0046] Figure 10 is the 13APT NMR spectrum of compound (2).

[0047] Figure 11 is the HPLC chromatogram of compound (2).

[0048] Figure 12 is the 13APT NMR spectrum of compound (21).

[0049] Figure 13 is the HPLC chromatogram of compound (21).

[0050] Figure 14 is the 13APT NMR spectrum of compound (24).

[0051] Figure 15 is the HPLC chromatogram of compound (24).

[0052] Figure 16 is the 13APT NMR spectrum of compound (23).

[0053] Figure 17 is the HPLC chromatogram of compound (23).

[0054] Figure 18 is the 13APT NMR spectrum of compound (7).

[0055] Figure 19 is the HPLC chromatogram of compound (7).

[0056] Figure 20 is the proton NMR spectrum of compound (25).

[0057] Figure 21 is the 13APT NMR spectrum of compound (25).

[0058] Figure 22 is the HPLC chromatogram of compound (25).

[0059] Figure 23are two chromatograms showing the chromatographic detection of compound (37) in a mixture with compound (10) using method 3 (top) and the chromatogram of authentic (37) (bottom). DETAILED DESCRIPTION

[0060] I. Compounds of the Disclosure

[0061] In one embodiment, the present disclosure provides a compound of Formula (I), or a salt or solvate thereof:

[0062]

[0063] wherein represents a single bond or a double bond.

[0064] In another embodiment, the present disclosure provides a compound of Formula (I), wherein represents a single bond, i.e. compound (1), or a salt or solvate thereof:

[0065]

[0066] In another embodiment, the present disclosure provides a compound of Formula (I), wherein represents a double bond, i.e. compound (2), or a salt or solvate thereof:

[0067]

[0068] In another embodiment, the present disclosure provides a compound of Formula (II):

[0069]

[0070] or a salt or solvate thereof, wherein represents a single bond or a double bond.

[0071] In another embodiment, the present disclosure provides a compound of Formula (II), wherein

[0072] represents a single bond, i.e. compound (3), or a salt or solvate thereof:

[0073]

[0074] In another embodiment, the present disclosure provides a compound of Formula (II), wherein 5represents a double bond, i.e. compound (4), or a salt or solvate thereof:

[0075]

[0076] In another embodiment, the present disclosure provides a compound of Formula (III):

[0077]

[0078] or a salt or solvate thereof, wherein represents a single bond or a double bond.

[0079] In another embodiment, the present disclosure provides a compound of Formula (III), wherein

[0080] represents a single bond, i.e., compound (5), or a salt or solvate thereof:

[0081]

[0082] In another embodiment, the present disclosure provides a compound of Formula (III), wherein represents a double bond, i.e., compound (6), or a salt or solvate thereof:

[0083]

[0084] In another embodiment, the present disclosure provides compound (21):

[0085]

[0086] or a salt or solvate thereof.

[0087] In another embodiment, the present disclosure provides compound (22):

[0088]

[0089] or a salt or solvate thereof.

[0090] In another embodiment, the present disclosure provides compound (23):

[0091]

[0092] or a salt or solvate thereof.

[0093] In another embodiment, the present disclosure provides compound (24):

[0094]

[0095] or a salt or solvate thereof.

[0096] In another embodiment, the present disclosure provides compound (25):

[0097]

[0098] or a salt or solvate thereof.

[0099] In another embodiment, the present disclosure provides a compound of Table 1, or a salt or solvate thereof.

[0100] Table 1

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110] The compounds in this Section I are collectively referred to as “Compounds of the Disclosure” and individually as “Compound of the Disclosure”.

[0111] II. Compositions of the Disclosure

[0112] In another embodiment, the present disclosure provides a composition comprising a Compound of the Disclosure.

[0113] In another embodiment, the present disclosure provides a composition comprising a compound of Formula (I). In another embodiment, the composition comprises 0.0001% to 99.9% of Formula (I) as determined by high performance liquid chromatography (HPLC) analysis, gas chromatography (GC) analysis, and / or a combination of HPLC and GC chromatography analysis.

[0114] In another embodiment, the present disclosure provides a composition comprising compound (1). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (1) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (1) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (1). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (1) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (1). The composition comprising compound (1) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (1) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0115] In another embodiment, the present disclosure provides a composition comprising compound (2). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (2) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (2) as measured by HPLC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (2). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (2) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (2). The composition comprising compound (2) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (2) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0116] In another embodiment, the present disclosure provides a compound of Formula (II), or salt or solvate thereof:

[0117]

[0118] wherein represents a single bond or a double bond.

[0119] In another embodiment, the present disclosure provides a compound of Formula (II), wherein represents a single bond, i.e., compound (3), or salt or solvate thereof:

[0120]

[0121] In another embodiment, the present disclosure provides a compound of Formula (II), wherein represents a double bond, i.e., compound (4), or salt or solvate thereof:

[0122]

[0123] In another embodiment, the present disclosure provides a composition comprising a compound of Formula (II), or salt or solvate thereof. In another embodiment, the composition comprises about 0.0001% to 99.9% of Formula (II) as measured by HPLC analysis.

[0124] In another embodiment, the present disclosure provides a composition comprising compound (3). In another embodiment, the composition comprises about 0.000001% to 99.9% of compound (3) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises about 0.0001% to 99.9% of compound (3) as measured by HPLC and / or GC analysis, for example, about 0.0001% to about 50%, about 0.0001% to about 25%, about 0.0001% to about 10%, about 0.0001% to about 5%, about 0.0001% to about 1%, about 50% to 99.9%, about 75% to 99.9%, about 90% to 99.9%, or about 95% to 99.9% of compound (3). In another embodiment, the composition comprises about 0.000001% to about 15% of compound (3) as measured by HPLC and / or GC analysis, for example, about 0.000001% to about 10%, about 0.000001% to about 5%, about 0.000001% to about 3%, about 0.000001% to about 1%, about 0.00001% to about 3%, about 0.00001% to about 1%, about 0.0001% to about 3%, about 0.0001% to about 1%, about 0.001% to about 3%, or about 0.001% to about 1% of compound (3). The composition comprising compound (3) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (3) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0125] In another embodiment, the present disclosure provides a composition comprising compound (4). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (4) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (4) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (4). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (4) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (4). The composition comprising compound (4) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (4) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0126] In another embodiment, the present disclosure provides a composition comprising compound (4) and compound (10). In another embodiment, the composition comprises from about 50% to 99.9% of compound (4) as measured by HPLC analysis, for example, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (4).

[0127] In another embodiment, the present disclosure provides a compound of Formula (III), or a salt or solvate thereof:

[0128]

[0129] wherein represents a single bond or a double bond.

[0130] In another embodiment, the present disclosure provides a compound of Formula (III), wherein represents a single bond, i.e., compound (5), or a salt or solvate thereof:

[0131]

[0132] In another embodiment, the present disclosure provides a compound of Formula (III), or a salt or solvate thereof, wherein represents a double bond, i.e., compound (6), or a salt or solvate thereof:

[0133]

[0134] In another embodiment, the present disclosure provides a composition comprising a compound of Formula (III), or a salt or solvate thereof. In another embodiment, the composition comprises about 0.0001% to 99.9% of Formula (III) as determined by HPLC analysis.

[0135] In another embodiment, the present disclosure provides a composition comprising compound (5). In another embodiment, the composition comprises about 0.000001% to 99.9% of compound (5) as determined by HPLC and / or GC analysis. In another embodiment, the composition comprises about 0.0001% to 99.9% of compound (5) as determined by HPLC and / or GC analysis, for example, about 0.0001% to about 50%, about 0.0001% to about 25%, about 0.0001% to about 10%, about 0.0001% to about 5%, about 0.0001% to about 1%, about 50% to 99.9%, about 75% to 99.9%, about 90% to 99.9%, or about 95% to 99.9% of compound (5). In another embodiment, the composition comprises about 0.000001% to about 15% of compound (5) as determined by HPLC and / or GC analysis, for example, about 0.000001% to about 10%, about 0.000001% to about 5%, about 0.000001% to about 3%, about 0.000001% to about 1%, about 0.00001% to about 3%, about 0.00001% to about 1%, about 0.0001% to about 3%, about 0.0001% to about 1%, about 0.001% to about 3%, or about 0.001% to about 1% of compound (5). The composition comprising compound (5) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (5) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0136] In another embodiment, the present disclosure provides a composition comprising compound (6). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (6) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (6) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (6). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (6) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (6). The composition comprising compound (6) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (6) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0137] In another embodiment, the present disclosure provides a composition comprising compound (7). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (7) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (7) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (7). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (7) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (7). The composition comprising compound (7) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (7) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0138] In another embodiment, the present disclosure provides a composition comprising compound (8). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (8) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (8) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (8). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (8) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (8). The composition comprising compound (8) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (8) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0139] In another embodiment, the present disclosure provides a composition comprising a compound of formula (IV):

[0140]

[0141] or salts or solvates thereof, wherein represents a single or double bond. In another embodiment, the composition comprises from about 50% to 99.9% of formula (IV) as measured by HPLC analysis, for example, from about 75% to 99.9%, from about 80% to 99.9%, from about 85% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of formula (IV).

[0142] In another embodiment, the present disclosure provides a composition comprising a compound of formula (IV), wherein represents a single bond, i.e., compound (9), or salts or solvates thereof:

[0143]

[0144] In another embodiment, the composition comprises about 25% to 99.9% of compound (9) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises about 50% to 99.9% of compound (9) as measured by HPLC and / or GC analysis, for example, about 75% to 99.9%, about 80% to 99.9%, about 85% to 99.9%, about 90% to 99.9%, or about 95% to 99.9% of compound (9).

[0145] In another embodiment, the present disclosure provides a composition comprising a compound of Formula (IV), wherein represents a double bond, i.e., compound (10), or a salt or solvate thereof:

[0146]

[0147] In another embodiment, the composition comprises about 25% to 99.9% of compound (10) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises about 50% to 99.9% of compound (10) as measured by HPLC and / or analysis, for example, about 75% to 99.9%, about 80% to 99.9%, about 85% to 99.9%, about 90% to 99.9%, or about 55% to 99.9% of compound (10). In another embodiment, the composition comprises about 25%, about 30%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 91%, about 92%, about 93%, about 94%, about 95%, about 96%, about 97%, about 98%, or about 99% of compound (10). A composition comprising compound (10) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. Such a composition can comprise about 0.000001% to about 15% of one or more other compounds of the present disclosure as measured by HPLC and / or GC analysis, for example, about 0.000001% to about 10%, about 0.000001% to about 5%, about 0.000001% to about 3%, about 0.000001% to about 1%, about 0.00001% to about 3%, about 0.00001% to about 1%, about 0.0001% to about 3%, about 0.0001% to about 1%, about 0.001% to about 3%, or about 0.001% to about 1% of one or more other compounds of the present disclosure.

[0148] In another embodiment, the present disclosure provides a composition comprising compound (11A). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (11A) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (11A) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (11A). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (11A) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (11A). The composition comprising compound (11A) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (11A) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0149] In another embodiment, this disclosure provides a composition comprising compound (11B). In another embodiment, the composition comprises about 0.000001% to 99.9% of compound (11B) as determined by HPLC and / or GC analysis. In another embodiment, the composition comprises about 0.0001% to 99.9% of compound (11B) as determined by HPLC and / or GC analysis, for example, about 0.0001% to about 50%, about 0.0001% to about 25%, about 0.0001% to about 10%, about 0.0001% to about 5%, about 0.0001% to about 1%, about 50% to 99.9%, about 75% to 99.9%, about 90% to 99.9%, or about 95% to 99.9% of compound (11B). In another embodiment, the composition comprises about 0.000001% to about 15% of compound (11B) as determined by HPLC and / or GC analysis, for example, about 0.000001% to about 10%, about 0.000001% to about 5%, about 0.000001% to about 3%, about 0.000001% to about 1%, about 0.00001% to about 3%, about 0.00001% to about 1%, about 0.0001% to about 3%, about 0.0001% to about 1%, about 0.001% to about 3%, about 0.0001% to about 1%, or about 0.001% to about 1%. The composition comprising compound (11B) may optionally contain one or more other compounds from the other compounds listed in Table 1 of this disclosure. In one embodiment, the composition comprising compound (11B) further comprises compound (10) and optionally one or more other compounds from the other compounds listed in Table 1 of this disclosure.

[0150] In another embodiment, the present disclosure provides a composition comprising compound (12). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (12) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (12) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (12). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (12) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (12). The composition comprising compound (12) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (12) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0151] In another embodiment, the present disclosure provides a composition comprising compound (13). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (13) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (13) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (13). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (13) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (13). The composition comprising compound (13) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (13) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0152] In another embodiment, the present disclosure provides a composition comprising compound (14). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (14) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (14) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (14). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (14) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (14). The composition comprising compound (14) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (14) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0153] In another embodiment, the present disclosure provides a composition comprising compound (15). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (15) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (15) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (15). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (15) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (15). The composition comprising compound (15) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (15) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0154] In another embodiment, this disclosure provides a composition comprising compound (16). In another embodiment, the composition comprises about 0.000001% to 99.9% of compound (16) as determined by HPLC and / or GC analysis. In another embodiment, the composition comprises about 0.0001% to 99.9% of compound (16) as determined by HPLC and / or GC analysis, for example, about 0.0001% to about 50%, about 0.0001% to about 25%, about 0.0001% to about 10%, about 0.0001% to about 5%, about 0.0001% to about 1%, about 50% to 99.9%, about 75% to 99.9%, about 90% to 99.9%, or about 95% to 99.9% of compound (16). In another embodiment, the composition comprises about 0.000001% to about 15% of compound (16) as determined by HPLC and / or GC analysis, for example, about 0.000001% to about 10%, about 0.000001% to about 5%, about 0.000001% to about 3%, about 0.000001% to about 1%, about 0.00001% to about 3%, about 0.00001% to about 1%, about 0.0001% to about 3%, about 0.0001% to about 1%, about 0.001% to about 3%, about 0.001% to about 3%, or about 0.001% to about 1%. The composition comprising compound (16) may optionally contain one or more other compounds from the other compounds of this disclosure listed in Table 1. In one embodiment, the composition comprising compound (16) further comprises compound (10) and optionally one or more other compounds from the other compounds of this disclosure listed in Table 1.

[0155] In another embodiment, the present disclosure provides a composition comprising compound (17). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (17) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (17) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (17). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (17) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (17). The composition comprising compound (17) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (17) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0156] In another embodiment, the present disclosure provides a composition comprising compound (18). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (18) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (18) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (118). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (18) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (18). The composition comprising compound (18) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (18) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0157] In another embodiment, the present disclosure provides a composition comprising compound (19). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (19) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (19) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (19). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (19) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (19). The composition comprising compound (19) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (19) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0158] In another embodiment, the present disclosure provides a composition comprising compound (20A). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (20A) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (20A) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (20A). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (20A) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (20A). The composition comprising compound (20A) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (20A) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0159] In another embodiment, the present disclosure provides a composition comprising compound (20B). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (20B), as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (20B), for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (20B), as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (20B), for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (20B), as measured by HPLC and / or GC analysis. The composition comprising compound (20B) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (20B) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0160] In another embodiment, the present disclosure provides a composition comprising compound (21). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (21) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (21) as measured by HPLC and / or analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (21). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (21) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (21). The composition comprising compound (21) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (21) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0161] In another embodiment, the present disclosure provides a composition comprising compound (22). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (22) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (22) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (22). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (22) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (22). The composition comprising compound (22) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (22) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0162] In another embodiment, the present disclosure provides a composition comprising compound (23). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (23) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 50% to 99.9% of compound (23), for example, from about 75% to 99.9%, from about 80% to 99.9%, from about 85% to 99.9%, from about 90% to 99.9%, or from about 55% to 99.9% of compound (23) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (23), for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (23) as measured by HPLC and / or GC analysis. The composition comprising compound (23) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (23) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0163] In another embodiment, the present disclosure provides a composition comprising compound (24). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (24) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 50% to 99.9% of compound (24) as measured by HPLC analysis, for example, from about 75% to 99.9%, from about 80% to 99.9%, from about 85% to 99.9%, from about 90% to 99.9%, or from about 55% to 99.9% of compound (24). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (24) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (24). The composition comprising compound (24) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (24) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0164] In another embodiment, the present disclosure provides a composition comprising compound (25). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (25) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (25) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (25). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (25) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (25). The composition comprising compound (25) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (25) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0165] In another embodiment, the present disclosure provides a composition comprising compound (26). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (26) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (26) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (26). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (26) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (26). The composition comprising compound (26) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (26) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0166] In another embodiment, the present disclosure provides a composition comprising compound (27A). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (27A) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (27A) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (27A). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (27A) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (27A). The composition comprising compound (27A) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (27A) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0167] In another embodiment, the present disclosure provides a composition comprising compound (27B). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (27B) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (27B) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (27B). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (27B) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (27B). The composition comprising compound (27B) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (27B) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0168] In another embodiment, the present disclosure provides a composition comprising compound (28). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (28) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (28) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (28). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (28) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (28). The composition comprising compound (28) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (28) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0169] In another embodiment, this disclosure provides a composition comprising compound (29). In another embodiment, the composition comprises about 0.000001% to 99.9% of compound (29) as determined by HPLC and / or GC analysis. In another embodiment, the composition comprises about 0.0001% to 99.9% of compound (29) as determined by HPLC and / or GC analysis, for example, about 0.0001% to about 50%, about 0.0001% to about 25%, about 0.0001% to about 10%, about 0.0001% to about 5%, about 0.0001% to about 1%, about 50% to 99.9%, about 75% to 99.9%, about 90% to 99.9%, or about 95% to 99.9% of compound (29). In another embodiment, the composition comprises about 0.000001% to about 15% of compound (29) as determined by HPLC and / or GC analysis, for example, about 0.000001% to about 10%, about 0.000001% to about 5%, about 0.000001% to about 3%, about 0.000001% to about 1%, about 0.00001% to about 3%, about 0.00001% to about 1%, about 0.0001% to about 3%, about 0.0001% to about 1%, about 0.001% to about 3%, about 0.001% to about 3%, or about 0.001% to about 1%. The composition comprising compound (29) may optionally contain one or more other compounds from the other compounds of this disclosure listed in Table 1. In one embodiment, the composition comprising compound (29) further comprises compound (10) and optionally one or more other compounds from the other compounds of this disclosure listed in Table 1.

[0170] In another embodiment, the present disclosure provides a composition comprising compound (30). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (30) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (30) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (30). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (30) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (30). The composition comprising compound (30) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (30) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0171] In another embodiment, the present disclosure provides a composition comprising compound (31). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (31) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (31) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (31). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (31) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (31). The composition comprising compound (31) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (31) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0172] In another embodiment, the present disclosure provides a composition comprising compound (32). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (32) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (32) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (32). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (32) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (32). The composition comprising compound (32) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (32) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0173] In another embodiment, the present disclosure provides a composition comprising compound (33). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (33) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (33) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (33). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (33) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (33). The composition comprising compound (33) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (33) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0174] In another embodiment, the present disclosure provides a composition comprising compound (34). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (34) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (34) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (34). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (34) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (34). The composition comprising compound (34) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (34) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0175] In another embodiment, the present disclosure provides a composition comprising compound (35). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (35) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (35) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (35). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (35) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (35). The composition comprising compound (35) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (35) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0176] In another embodiment, the present disclosure provides a composition comprising compound (36). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (36) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (36) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (36). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (36) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (36). The composition comprising compound (36) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (36) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0177] In another embodiment, the present disclosure provides a composition comprising compound (37). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (37) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (37) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (37). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (37) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (37). The composition comprising compound (37) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (37) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0178] In another embodiment, the present disclosure provides a composition comprising compound (38). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (38) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (38) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (38). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (38) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (38). The composition comprising compound (38) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (38) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0179] In another embodiment, the present disclosure provides a composition comprising compound (39). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (39) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (39) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (39). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (39) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (39). The composition comprising compound (39) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (39) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0180] In another embodiment, the present disclosure provides a composition comprising compound (40). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (40) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (40) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (40). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (40) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (40). The composition comprising compound (0) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (40) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0181] In another embodiment, the present disclosure provides a composition comprising compound (41). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (41) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (41) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (41). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (41) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (41). The composition comprising compound (41) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (41) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0182] In another embodiment, the present disclosure provides a composition comprising compound (42). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (42) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (42) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (42). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (42) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (42). The composition comprising compound (42) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (42) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0183] In another embodiment, the present disclosure provides a composition comprising compound (43). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (43) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (43) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (43). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (43) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (43). The composition comprising compound (43) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (43) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0184] In another embodiment, this disclosure provides a composition comprising compound (44). In another embodiment, the composition comprises about 0.000001% to 99.9% of compound (44) as determined by HPLC and / or GC analysis. In another embodiment, the composition comprises about 0.0001% to 99.9% of compound (44) as determined by HPLC and / or GC analysis, for example, about 0.0001% to about 50%, about 0.0001% to about 25%, about 0.0001% to about 10%, about 0.0001% to about 5%, about 0.0001% to about 1%, about 50% to 99.9%, about 75% to 99.9%, about 90% to 99.9%, or about 95% to 99.9% of compound (44). In another embodiment, the composition comprises about 0.000001% to about 15% of compound (44) as determined by HPLC and / or GC analysis, for example, about 0.000001% to about 10%, about 0.000001% to about 5%, about 0.000001% to about 3%, about 0.000001% to about 1%, about 0.00001% to about 3%, about 0.00001% to about 1%, about 0.0001% to about 3%, about 0.0001% to about 1%, about 0.001% to about 3%, about 0.0001% to about 1%, or about 0.001% to about 1%. The composition comprising compound (44) may optionally contain one or more other compounds from the other compounds listed in Table 1 of this disclosure. In one embodiment, the composition comprising compound (44) further comprises compound (10) and optionally one or more other compounds from the other compounds listed in Table 1 of this disclosure.

[0185] In another embodiment, the present disclosure provides a composition comprising compound (45). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (45) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (45) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (45). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (45) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (45). The composition comprising compound (45) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (45) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0186] In another embodiment, the present disclosure provides a composition comprising compound (46). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (46) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (46) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (46). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (46) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (46). The composition comprising compound (46) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (46) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0187] In another embodiment, the present disclosure provides a composition comprising compound (47). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (47) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (47) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (47). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (47) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (47). The composition comprising compound (47) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (47) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0188] In another embodiment, the present disclosure provides a composition comprising compound (48). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (48) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (48) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (48). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (48) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (48). The composition comprising compound (48) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (48) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0189] In another embodiment, the present disclosure provides a composition comprising compound (49). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (49) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (49) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (49). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (49) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (49). The composition comprising compound (49) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (49) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0190] In another embodiment, the present disclosure provides a composition comprising compound (50). In another embodiment, the composition comprises from about 0.000001% to 99.9% of compound (50) as measured by HPLC and / or GC analysis. In another embodiment, the composition comprises from about 0.0001% to 99.9% of compound (50) as measured by HPLC and / or GC analysis, for example, from about 0.0001% to about 50%, from about 0.0001% to about 25%, from about 0.0001% to about 10%, from about 0.0001% to about 5%, from about 0.0001% to about 1%, from about 50% to 99.9%, from about 75% to 99.9%, from about 90% to 99.9%, or from about 95% to 99.9% of compound (50). In another embodiment, the composition comprises from about 0.000001% to about 15% of compound (50) as measured by HPLC and / or GC analysis, for example, from about 0.000001% to about 10%, from about 0.000001% to about 5%, from about 0.000001% to about 3%, from about 0.000001% to about 1%, from about 0.00001% to about 3%, from about 0.00001% to about 1%, from about 0.0001% to about 3%, from about 0.0001% to about 1%, from about 0.001% to about 3%, or from about 0.001% to about 1% of compound (50). The composition comprising compound (50) can optionally contain any one or more of the other compounds of the present disclosure listed in Table 1. In one embodiment, the composition comprising compound (50) further comprises compound (10) and optionally any one or more of the other compounds of the present disclosure listed in Table 1.

[0191] In another embodiment, the present disclosure provides a composition comprising a compound of Formula (IV) (e.g., compound (9) or compound (10)), or a salt or solvate thereof; and:

[0192] (a) a compound of Formula (I) (e.g., compound (1) or compound (2)), or a salt or solvate thereof:

[0193] or

[0194] (b) a compound of Formula (II) (e.g., compound (3) or compound (4)), or a salt or solvate thereof:

[0195] or

[0196] (c) a compound of Formula (III) (e.g., compound (5) or compound (6)), or a salt or solvate thereof:

[0197] or (d) compound (7) or a salt or solvate thereof:

[0198] or (e) compound (8) or a salt or solvate thereof:

[0199] or (f) compound (11A) or a salt or solvate thereof:

[0200] or (g) compound (11B) or a salt or solvate thereof:

[0201] or (h) compound (20A) or a salt or solvate thereof:

[0202] or (i) compound (20B) or a salt or solvate thereof:

[0203] or (j) compound (21) or a salt or solvate thereof:

[0204] or (k) compound (22) or a salt or solvate thereof:

[0205] or (1) compound (23) or a salt or solvate thereof:

[0206] or (m) compound (24) or a salt or solvate thereof:

[0207] or (n) compound (25) or a salt or solvate thereof:

[0208] or

[0209] (o) compound (37) or a salt or solvate thereof:

[0210] or

[0211] (p) a combination of: a compound of Formula (I), or a salt or solvate thereof; a compound of Formula (II), or a salt or solvate thereof; a compound of Formula (III), or a salt or solvate thereof; compound (7), or a salt or solvate thereof; compound (8), or a salt or solvate thereof; compound (11A), or a salt or solvate thereof; compound (11B), or a salt or solvate thereof; compound (20A), or a salt or solvate thereof; compound (20B), or a salt or solvate thereof; compound (21), or a salt or solvate thereof; compound (22), or a salt or solvate thereof; compound (23), or a salt or solvate thereof; compound (24), or a salt or solvate thereof; compound (25), or a salt or solvate thereof; and / or compound (37), or a salt or solvate thereof,

[0212] wherein represents a single or double bond.

[0213] In another embodiment, the present disclosure provides a composition comprising a compound of Formula (IV), or a salt or solvate thereof, and a compound of Formula (I), or a salt or solvate thereof. In another embodiment, the composition comprises Formula (IV) and about 0.001% to about 10% of Formula (I), e.g., about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, or about 0.05% to about 0.5% of Formula (I) as determined by HPLC analysis. In another embodiment, the composition comprises Formula (IV) and about 0.01%, about 0.02%, about 0.03%, about 0.04%, about 0.05%, about 0.06%, about 0.07%, about 0.08%, about 0.09%, about 0.1%, about 0.11%, about 0.12%, about 0.13%, about 0.14%, about 0.15%, about 0.16%, about 0.17%, about 0.18%, about 0.19%, about 0.2%, about 0.3%, about 0.4%, about 0.5%, about 0.6%, about 0.7%, about 0.8%, about 0.9%, or about 1% of Formula (I). In another embodiment, the compound of Formula (IV) is compound (9). In another embodiment, the compound of Formula (IV) is compound (10). In another embodiment, the compound of Formula (I) is compound (1). In another embodiment, the compound of Formula (I) is compound (2).

[0214] In another embodiment, the present disclosure provides a composition comprising a compound of Formula (IV), or salt or solvate thereof, and a compound of Formula (I), or salt or solvate thereof, wherein the weight ratio of Formula (I) to Formula (IV) is 0.001 to 0.1, for example, 0.001 to 0.05, 0.001 to 0.01, or 0.001 to 0.005 of Formula (I): Formula (IV). In another embodiment, the compound of Formula (IV) is compound (10). In another embodiment, the compound of Formula (I) is compound (1). In another embodiment, the compound of Formula (I) is compound (2).

[0215] In another embodiment, the present disclosure provides a composition comprising a compound of Formula (IV), or salt or solvate thereof, and a compound of Formula (II), or salt or solvate thereof. In another embodiment, the composition comprises Formula (IV) and about 0.001% to about 10% of Formula (II) as measured by HPLC analysis, for example, about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of Formula (II). In another embodiment, the composition comprises Formula (IV) and about 0.01%, about 0.2%, about 0.21%, about 0.22%, about 0.23%, about 0.24%, about 0.25%, about 0.26%, about 0.27%, about 0.28%, about 0.29%, about 0.3%, about 0.31%, about 0.32%, about 0.33%, about 0.34%, about 0.35%, about 0.36%, about 0.37%, about 0.38%, about 0.39%, about 0.4%, about 0.41%, about 0.42%, about 0.43%, about 0.44%, about 0.45%, about 0.46%, about 0.47%, about 0.48%, about 0.49%, about 0.5%, about 0.6%, about 0.7%, about 0.8%, about 0.9%, or about 1% of Formula (II). In another embodiment, the compound of Formula (IV) is compound (9). In another embodiment, the compound of Formula (IV) is compound (10). In another embodiment, the compound of Formula (II) is compound (3). In another embodiment, the compound of Formula (II) is compound (4).

[0216] In another embodiment, the present disclosure provides a composition comprising a compound of Formula (IV), or salt or solvate thereof, and a compound of Formula (II), or salt or solvate thereof, wherein the weight ratio of Formula (II) to Formula (IV) is 0.001 to 0.1, for example, 0.001 to 0.05, 0.001 to 0.01, or 0.001 to 0.005 of Formula (II): Formula (IV). In another embodiment, the compound of Formula (IV) is compound (9). In another embodiment, the compound of Formula (IV) is compound (10). In another embodiment, the compound of Formula (II) is compound (3). In another embodiment, the compound of Formula (II) is compound (4).

[0217] In another embodiment, the present disclosure provides a composition comprising a compound of Formula (IV), or salt or solvate thereof, and a compound of Formula (III), or salt or solvate thereof. In another embodiment, the composition comprises Formula (IV) and about 0.001% to about 10% of Formula (III) as measured by HPLC analysis, for example, about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, or about 0.1% to about 5% of Formula (III). In another embodiment, the compound of Formula (IV) is compound (9). In another embodiment, the compound of Formula (IV) is compound (10). In another embodiment, the compound of Formula (III) is compound (5). In another embodiment, the compound of Formula (III) is compound (6).

[0218] In another embodiment, the present disclosure provides a composition comprising a compound of Formula (IV), or salt or solvate thereof, and a compound of Formula (III), or salt or solvate thereof, wherein the weight ratio of Formula (III) to Formula (IV) is 0.001 to 0.1, for example, 0.001 to 0.05, 0.001 to 0.01, or 0.001 to 0.005 of Formula (III): Formula (IV). In another embodiment, the compound of Formula (IV) is compound (9). In another embodiment, the compound of Formula (IV) is compound (10). In another embodiment, the compound of Formula (III) is compound (5). In another embodiment, the compound of Formula (III) is compound (6).

[0219] In another embodiment, the present disclosure provides a composition comprising a compound of Formula (IV), or salt or solvate thereof, and compound (7), or salt or solvate thereof. In another embodiment, the composition comprises Formula (IV) and about 0.001% to about 10% of compound (7), e.g., about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, or about 0.1% to about 5% of compound (7), as determined by HPLC analysis. In another embodiment, the compound of Formula (IV) is compound (9). In another embodiment, the compound of Formula (IV) is compound (10).

[0220] In another embodiment, the present disclosure provides a composition comprising a compound of Formula (IV), or salt or solvate thereof, and compound (7), or salt or solvate thereof, wherein the weight ratio of compound (7) to Formula (IV) is 0.001 to 0.1, e.g., 0.001 to 0.05, 0.001 to 0.01, or 0.001 to 0.005 of compound (7): Formula (IV). In another embodiment, the compound of Formula (IV) is compound (9). In another embodiment, the compound of Formula (IV) is compound (10).

[0221] In another embodiment, the present disclosure provides a composition comprising a compound of Formula (IV), or salt or solvate thereof, and compound (8), or salt or solvate thereof. In another embodiment, the composition comprises Formula (IV) and about 0.001% to about 10% of compound (8), e.g., about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, or about 0.1% to about 5% of compound (8), as determined by HPLC analysis. In another embodiment, the compound of Formula (IV) is compound (9). In another embodiment, the compound of Formula (IV) is compound (10).

[0222] In another embodiment, the present disclosure provides a composition comprising a compound of Formula (IV), or salt or solvate thereof, and compound (8), or salt or solvate thereof, wherein the weight ratio of compound (8) to Formula (IV) is 0.001 to 0.1, e.g., 0.001 to 0.05, 0.001 to 0.01, or 0.001 to 0.005 of compound (8): Formula (IV). In another embodiment, the compound of Formula (IV) is compound (9). In another embodiment, the compound of Formula (IV) is compound (10).

[0223] In another embodiment, the present disclosure provides a composition comprising a compound of Formula (IV), or salt or solvate thereof, and compound (11), or salt or solvate thereof. In another embodiment, the composition comprises Formula (IV) and about 0.001% to about 10% of compound (11), e.g., about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, or about 0.1% to about 5% of compound (11), as measured by HPLC analysis. In another embodiment, the composition comprises about 0.01%, about 0.02%, about 0.03%, about 0.04%, about 0.05%, about 0.06%, about 0.07%, about 0.08%, about 0.09%, about 0.1%, about 0.11%, about 0.12%, about 0.13%, about 0.14%, about 0.15%, about 0.16%, about 0.17%, about 0.18%, about 0.19%, about 0.2%, about 0.21%, about 0.22%, about 0.23%, about 0.24%, about 0.25%, about 0.26%, about 0.27%, about 0.28%, about 0.29%, about 0.3%, about 0.4%, about 0.5%, about 0.6%, about 0.7%, about 0.8%, about 0.9%, or about 1% of compound (11). In another embodiment, the compound of Formula (IV) is compound (9). In another embodiment, the compound of Formula (IV) is compound (10).

[0224] In another embodiment, the present disclosure provides a composition comprising a compound of Formula (IV), or salt or solvate thereof, and compound (11A), or salt or solvate thereof, wherein the weight ratio of compound (11A) to Formula (IV) is 0.001 to 0.1, e.g., 0.001 to 0.05, 0.001 to 0.01, or 0.001 to 0.005 of compound (11A): Formula (IV). In another embodiment, the compound of Formula (IV) is compound (9). In another embodiment, the compound of Formula (IV) is compound (10).

[0225] In another embodiment, the present disclosure provides a composition comprising a compound of Formula (IV), or salt or solvate thereof, and compound (11B), or salt or solvate thereof, wherein the weight ratio of compound (11B) to Formula (IV) is 0.001 to 0.1, for example, 0.001 to 0.05, 0.001 to 0.01, or 0.001 to 0.005 of compound (11B): Formula (IV). In another embodiment, the compound of Formula (IV) is compound (9). In another embodiment, the compound of Formula (IV) is compound (10).

[0226] In another embodiment, the present disclosure provides a composition comprising a compound of Formula (IV), or salt or solvate thereof, and compound (20A), or salt or solvate thereof, wherein the weight ratio of compound (20A) to Formula (IV) is 0.001 to 0.1, for example, 0.001 to 0.05, 0.001 to 0.01, or 0.001 to 0.005 of compound (20A): Formula (IV). In another embodiment, the compound of Formula (IV) is compound (9). In another embodiment, the compound of Formula (IV) is compound (10).

[0227] In another embodiment, the present disclosure provides a composition comprising a compound of Formula (IV), or salt or solvate thereof, and compound (20B), or salt or solvate thereof, wherein the weight ratio of compound (20B) to Formula (IV) is 0.001 to 0.1, for example, 0.001 to 0.05, 0.001 to 0.01, or 0.001 to 0.005 of compound (20B): Formula (IV). In another embodiment, the compound of Formula (IV) is compound (9). In another embodiment, the compound of Formula (IV) is compound (10).

[0228] In another embodiment, the present disclosure provides a composition comprising a compound of Formula (IV), or salt or solvate thereof, and compound (21), or salt or solvate thereof, wherein the weight ratio of compound (21) to Formula (IV) is 0.001 to 0.1, for example, 0.001 to 0.05, 0.001 to 0.01, or 0.001 to 0.005 of compound (21): Formula (IV). In another embodiment, the compound of Formula (IV) is compound (9). In another embodiment, the compound of Formula (IV) is compound (10).

[0229] In another embodiment, the present disclosure provides a composition comprising compound (10), or a salt or solvate thereof, and compound (21), or a salt or solvate thereof.

[0230] In another embodiment, the present disclosure provides a composition comprising compound (10), or a salt or solvate thereof, and compound (21), or a salt or solvate thereof, wherein the weight ratio of compound (21) to compound (10) is 0.0001 to 0.1, for example, 0.001 to 0.05, 0.001 to 0.01, or 0.001 to 0.005 of compound (21): compound (10).

[0231] In another embodiment, the present disclosure provides a composition comprising compound (10), or a salt or solvate thereof, and compound (21), or a salt or solvate thereof.

[0232] In another embodiment, the present disclosure provides a composition comprising compound (10), or a salt or solvate thereof, and compound (21), or a salt or solvate thereof, wherein the weight ratio of compound (21) to compound (10) is 0.0001 to 0.1, for example, 0.001 to 0.05, 0.001 to 0.01, or 0.001 to 0.005 of compound (21): compound (10).

[0233] In another embodiment, the present disclosure provides a composition comprising compound (10), or a salt or solvate thereof, and compound (21), or a salt or solvate thereof.

[0234] In another embodiment, the present disclosure provides a composition comprising compound (10), or a salt or solvate thereof, and compound (21), or a salt or solvate thereof, wherein the weight ratio of compound (21) to compound (10) is 0.0001 to 0.1, for example, 0.001 to 0.05, 0.001 to 0.01, or 0.001 to 0.005 of compound (21): compound (10).

[0235] In another embodiment, the present disclosure provides a composition comprising a compound of Formula (IV), or a salt or solvate thereof, and compound (22), or a salt or solvate thereof, wherein the weight ratio of compound (22) to Formula (IV) is 0.001 to 0.1, for example, 0.001 to 0.05, 0.001 to 0.01, or 0.001 to 0.005 of compound (22): Formula (IV). In another embodiment, the compound of Formula (IV) is compound (9). In another embodiment, the compound of Formula (IV) is compound (10).

[0236] In another embodiment, the present disclosure provides a composition comprising compound (10), or a salt or solvate thereof, and compound (22), or a salt or solvate thereof.

[0237] In another embodiment, the present disclosure provides a composition comprising compound (10), or a salt or solvate thereof, and compound (22), or a salt or solvate thereof, wherein the weight ratio of compound (22) to compound (10) is 0.0001 to 0.1, for example, 0.001 to 0.05, 0.001 to 0.01, or 0.001 to 0.005 of compound (22): compound (10).

[0238] In another embodiment, the present disclosure provides a composition comprising compound (10), or a salt or solvate thereof, and compound (22), or a salt or solvate thereof.

[0239] In another embodiment, the present disclosure provides a composition comprising compound (10), or a salt or solvate thereof, and compound (22), or a salt or solvate thereof, wherein the weight ratio of compound (22) to compound (10) is 0.0001 to 0.1, for example, 0.001 to 0.05, 0.001 to 0.01, or 0.001 to 0.005 of compound (22): compound (10).

[0240] In another embodiment, the present disclosure provides a composition comprising a compound of Formula (IV), or salt or solvate thereof, and compound (23), or salt or solvate thereof, wherein the weight ratio of compound (23) to Formula (IV) is 0.0001 to 0.1, for example, 0.001 to 0.05, 0.001 to 0.01, or 0.001 to 0.005 of compound (23): Formula (IV). In another embodiment, the compound of Formula (IV) is compound (9). In another embodiment, the compound of Formula (IV) is compound (10).

[0241] In another embodiment, the present disclosure provides a composition comprising compound (10), or salt or solvate thereof, and compound (23), or salt or solvate thereof.

[0242] In another embodiment, the present disclosure provides a composition comprising compound (10), or salt or solvate thereof, and compound (23), or salt or solvate thereof, wherein the weight ratio of compound (23) to compound (10) is 0.0001 to 0.1, for example, 0.001 to 0.05, 0.001 to 0.01, or 0.001 to 0.005 of compound (23): compound (10).

[0243] In another embodiment, the present disclosure provides a composition comprising a compound of Formula (IV), or salt or solvate thereof, and compound (24), or salt or solvate thereof, wherein the weight ratio of compound (24) to Formula (IV) is 0.0001 to 0.1, for example, 0.001 to 0.05, 0.001 to 0.01, or 0.001 to 0.005 of compound (24): Formula (IV). In another embodiment, the compound of Formula (IV) is compound (9). In another embodiment, the compound of Formula (IV) is compound (10).

[0244] In another embodiment, the present disclosure provides a composition comprising compound (10), or salt or solvate thereof, and compound (24), or salt or solvate thereof.

[0245] In another embodiment, the present disclosure provides a composition comprising compound (10), or salt or solvate thereof, and compound (24), or salt or solvate thereof, wherein the weight ratio of compound (24) to compound (10) is 0.0001 to 0.1, for example, 0.001 to 0.05, 0.001 to 0.01, or 0.001 to 0.005 of compound (24): compound (10).

[0246] In another embodiment, the present disclosure provides a composition comprising a compound of Table 1.

[0247] In another embodiment, the present disclosure provides a composition comprising compound (10) and at least one other compound of Table 1.

[0248] In another embodiment, the present disclosure provides a composition comprising about 80% to about 99% of compound (10), for example about 85% to about 99%, about 90% to about 99%, or about 95% to about 99% of compound (10), and 0.0001% to 5% of at least one other compound of Table 1, for example 0.001% to 3%, 0.001 to 1%, 0.01% to 1%, or 0.1% to 1% of the at least one other compound of Table 1.

[0249] In another embodiment, the present disclosure provides a composition comprising about 80% to about 99% of compound (10), for example about 85% to about 99%, about 90% to about 99%, or about 95% to about 99% of compound (10), and 0.0001% to 5% of compound (2), for example 0.001% to 3%, 0.001 to 1%, 0.01% to 1%, or 0.1% to 1% of compound (2).

[0250] In another embodiment, the present disclosure provides a composition comprising about 80% to about 99% of compound (10), for example about 85% to about 99%, about 90% to about 99%, or about 95% to about 99% of compound (10), and 0.0001% to 5% of compound (21), for example 0.001% to 3%, 0.001 to 1%, 0.01% to 1%, or 0.1% to 1% of compound (21).

[0251] In another embodiment, the present disclosure provides a composition comprising about 80% to about 99% of compound (10), for example about 85% to about 99%, about 90% to about 99%, or about 95% to about 99% of compound (10), and 0.0001% to 5% of compound (2), for example 0.001% to 3%, 0.001 to 1%, 0.01% to 1%, or 0.1% to 1% of compound (2), and 0.0001% to 5% of compound (21), for example 0.001% to 3%, 0.001 to 1%, 0.01% to 1%, or 0.1% to 1% of compound (21).

[0252] In another embodiment, the present disclosure provides a composition comprising about 80% to about 99% of compound (10), for example about 85% to about 99%, about 90% to about 99%, or about 95% to about 99% of compound (10), and 0.0001% to 5% of compound (22), for example 0.001% to 3%, 0.001 to 1%, 0.01% to 1%, or 0.1% to 1% of compound (22).

[0253] In another embodiment, the present disclosure provides a composition comprising about 80% to about 99% of compound (10), for example about 85% to about 99%, about 90% to about 99%, or about 95% to about 99% of compound (10), and 0.0001% to 5% of compound (23), for example 0.001% to 3%, 0.001 to 1%, 0.01% to 1%, or 0.1% to 1% of compound (23).

[0254] In another embodiment, the present disclosure provides a composition comprising about 80% to about 99% of compound (10), for example about 85% to about 99%, about 90% to about 99%, or about 95% to about 99% of compound (10), and 0.0001% to 5% of compound (24), for example 0.001% to 3%, 0.001 to 1%, 0.01% to 1%, or 0.1% to 1% of compound (24).

[0255] The present disclosure provides the following specific composition embodiments regarding compositions comprising compound (10).

[0256] Composition Embodiment 1. A composition comprising:

[0257] (i) compound (10), or a salt or solvate thereof; and

[0258] (ii) one or more molecules, or a salt or solvate thereof,

[0259] wherein the one or more molecules are selected from the group consisting of compounds (1)-(9), (11A), (11B), (12)-(19), (20A), (20B), (21)-(26), (27A), (27B), and (28)-(50) of Table 1, or a combination thereof.

[0260] Composition Embodiment 2. The composition according to composition embodiment 1, wherein the composition comprises compound (1) in a molecular form.

[0261] Composition Embodiment 3. The composition according to composition embodiment 1 or 2, wherein the composition comprises compound (2) in a molecular form.

[0262] Composition Embodiment 4. The composition according to any one of Composition Embodiments 1 to 3, wherein the composition comprises compound (3) in molecular form.

[0263] Composition Embodiment 5. The composition according to any one of Composition Embodiments 1 to 4, wherein the composition comprises compound (4) in molecular form.

[0264] Composition Embodiment 6. The composition according to any one of Composition Embodiments 1 to 5, wherein the composition comprises compound (5) in molecular form.

[0265] Composition Embodiment 7. The composition according to any one of Composition Embodiments 1 to 6, wherein the composition comprises compound (6) in molecular form.

[0266] Composition Embodiment 8. The composition according to any one of Composition Embodiments 1 to 7, wherein the composition comprises compound (7) in molecular form.

[0267] Composition Embodiment 9. The composition according to any one of Composition Embodiments 1 to 8, wherein the composition comprises compound (8) in molecular form.

[0268] Composition Embodiment 10. The composition according to any one of Composition Embodiments 1 to 9, wherein the composition comprises compound (9) in molecular form.

[0269] Composition Embodiment 11. The composition according to any one of Composition Embodiments 1 to 10, wherein the composition comprises compound (11A) in molecular form.

[0270] Composition Embodiment 12. The composition according to any one of Composition Embodiments 1 to 11, wherein the composition comprises compound (11B) in molecular form.

[0271] Composition Embodiment 13. The composition according to any one of Composition Embodiments 1 to 12, wherein the composition comprises compound (12) in molecular form.

[0272] Composition Embodiment 14. The composition according to any one of Composition Embodiments 1 to 12, wherein the composition comprises compound (13) in molecular form.

[0273] Composition Embodiment 15. The composition according to any one of Composition Embodiments 1 to 14, wherein the composition comprises compound (14) in molecular form.

[0274] Composition Embodiment 16. The composition according to any one of Composition Embodiments 1 to 15, wherein the composition comprises compound (15) in molecular form.

[0275] Composition Embodiment 17. The composition according to any one of Composition Embodiments 1 to 16, wherein the composition comprises compound (16) in molecular form.

[0276] Composition Embodiment 18. The composition according to any one of Composition Embodiments 1 to 17, wherein the composition comprises compound (17) in molecular form.

[0277] Composition Embodiment 19. The composition according to any one of Composition Embodiments 1 to 18, wherein the composition comprises compound (18) in molecular form.

[0278] Composition Embodiment 20. The composition according to any one of Composition Embodiments 1 to 19, wherein the composition comprises compound (19) in molecular form.

[0279] Composition Embodiment 21. The composition according to any one of Composition Embodiments 1 to 20, wherein the composition comprises compound (20A) in molecular form.

[0280] Composition Embodiment 22. The composition according to any one of Composition Embodiments 1 to 21, wherein the composition comprises compound (20B) in molecular form.

[0281] Composition Embodiment 23. The composition according to any one of Composition Embodiments 1 to 22, wherein the composition comprises compound (21) in molecular form.

[0282] Composition Embodiment 24. The composition according to any one of Composition Embodiments 1 to 23, wherein the composition comprises compound (22) in molecular form.

[0283] Composition Embodiment 25. The composition according to any one of Composition Embodiments 1 to 24, wherein the composition comprises compound (23) in molecular form.

[0284] Composition Embodiment 26. The composition according to any one of Composition Embodiments 1 to 25, wherein the composition comprises compound (24) in molecular form.

[0285] Composition Embodiment 27. The composition according to any one of Composition Embodiments 1 to 26, wherein the composition comprises compound (25) in molecular form.

[0286] Composition Embodiment 28. The composition according to any one of Composition Embodiments 1 to 27, wherein the composition comprises compound (26) in molecular form.

[0287] Composition Embodiment 29. The composition according to any one of Composition Embodiments 1 to 28, wherein the composition comprises compound (27A) in molecular form.

[0288] Composition Embodiment 30. The composition according to any one of Composition Embodiments 1 to 29, wherein the composition comprises compound (27B) in molecular form.

[0289] Composition Embodiment 31. The composition according to any one of Composition Embodiments 1 to 30, wherein the composition comprises compound (28) in molecular form.

[0290] Composition Embodiment 32. The composition according to any one of Composition Embodiments 1 to 31, wherein the composition comprises compound (29) in molecular form.

[0291] Composition Embodiment 33. The composition according to any one of Composition Embodiments 1 to 32, wherein the composition comprises compound (30) in molecular form.

[0292] Composition Embodiment 34. The composition according to any one of Composition Embodiments 1 to 33, wherein the composition comprises compound (31) in molecular form.

[0293] Composition Embodiment 35. The composition according to any one of Composition Embodiments 1 to 34, wherein the composition comprises compound (32) in molecular form.

[0294] Composition Embodiment 36. The composition according to any one of Composition Embodiments 1 to 35, wherein the composition comprises compound (33) in molecular form.

[0295] Composition Embodiment 37. The composition according to any one of Composition Embodiments 1 to 36, wherein the composition comprises compound (34) in molecular form.

[0296] Composition Embodiment 38. The composition according to any one of Composition Embodiments 1 to 37, wherein the composition comprises compound (35) in molecular form.

[0297] Composition Embodiment 39. The composition according to any one of Composition Embodiments 1 to 38, wherein the composition comprises compound (36) in molecular form.

[0298] Composition Embodiment 40. The composition according to any one of Composition Embodiments 1 to 39, wherein the composition comprises compound (37) in molecular form.

[0299] Composition Embodiment 41. The composition according to any one of Composition Embodiments 1 to 40, wherein the composition comprises compound (38) in molecular form.

[0300] Composition Embodiment 42. The composition according to any one of Composition Embodiments 1 to 41, wherein the composition comprises compound (39) in molecular form.

[0301] Composition Embodiment 43. The composition according to any one of Composition Embodiments 1 to 2, wherein the composition comprises compound (40) in molecular form.

[0302] Composition Embodiment 44. The composition according to any one of Composition Embodiments 1 to 43, wherein the composition comprises compound (41) in molecular form.

[0303] Composition Embodiment 45. The composition according to any one of Composition Embodiments 1 to 44, wherein the composition comprises compound (42) in molecular form.

[0304] Composition Embodiment 46. The composition according to any one of Composition Embodiments 1 to 45, wherein the composition comprises compound (43) in molecular form.

[0305] Composition Embodiment 47. The composition according to any one of Composition Embodiments 1 to 46, wherein the composition comprises compound (44) in molecular form.

[0306] Composition Embodiment 48. The composition according to any one of Composition Embodiments 1 to 47, wherein the composition comprises compound (45) in molecular form.

[0307] Composition Embodiment 49. The composition according to any one of Composition Embodiments 1 to 48, wherein the composition comprises compound (46) in molecular form.

[0308] Composition Embodiment 50. The composition according to any one of Composition Embodiments 1 to 49, wherein the composition comprises compound (47) in molecular form.

[0309] Composition Embodiment 51. The composition according to any one of Composition Embodiments 1 to 50, wherein the composition comprises compound (48) in molecular form.

[0310] Composition Embodiment 52. The composition according to any one of Composition Embodiments 1 to 51, wherein the composition comprises compound (49) in molecular form.

[0311] Composition Embodiment 53. The composition according to any one of Composition Embodiments 1 to 52, wherein the composition comprises compound (50) in molecular form.

[0312] Composition Embodiment 54. The composition according to Composition Embodiment 1, wherein the composition comprises compound (2) and compound (21) in molecular form.

[0313] Composition Embodiment 55. The composition according to Composition Embodiment 1, wherein the composition comprises compound (2) and compound (25) in molecular form.

[0314] Composition Embodiment 56. The composition according to Composition Embodiment 1, wherein the composition comprises compound (2) and compound (37) in molecular form.

[0315] Composition Embodiment 57. The composition according to Composition Embodiment 1, wherein the composition comprises compound (21) and compound (25) in molecular form.

[0316] Composition Embodiment 58. The composition according to Composition Embodiment 1, wherein the composition comprises compound (21) and compound (37) in molecular form.

[0317] Composition Embodiment 59. The composition according to Composition Embodiment 1, wherein the composition comprises compound (25) and compound (37) in molecular form.

[0318] Composition Embodiment 60. The composition according to Composition Embodiment 1, wherein the composition comprises compound (2), compound (21), and compound (25) in molecular form.

[0319] Composition Embodiment 61. The composition according to Composition Embodiment 1, wherein the composition comprises compound (2), compound (21), and compound (37) in molecular form.

[0320] Composition Embodiment 62. The composition according to Composition Embodiment 1, wherein the composition comprises compound (2), compound (25), and compound (37) in molecular form.

[0321] Composition Embodiment 63. The composition according to Composition Embodiment 1, wherein the composition comprises compound (21), compound (25), and compound (37) in molecular form.

[0322] Composition Embodiment 64. The composition of any one of Composition Embodiments 1, wherein the composition comprises compound (2), compound (21), compound (25), and compound (37) in molecular form.

[0323] Composition Embodiment 65. The composition of any one of Composition Embodiments 5 to 66, comprising about 25% to about 99% of compound (10) as measured by HPLC and / or GC analysis.

[0324] Composition Embodiment 66. The composition of Composition Embodiment 65, comprising about 50% to about 99% of compound (10) as measured by HPLC and / or GC analysis.

[0325] Composition Embodiment 67. The composition of Composition Embodiment 67, comprising about 89% to about 99% of compound (10) as measured by HPLC and / or GC analysis.

[0326] Composition Embodiment 68. The composition of any one of Composition Embodiments 5 to 66, comprising about 10%, about 15%, about 20%, about 25%, about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 80%, about 85%, about 90%, about 95%, about 96%, about 97%, about 98%, or about 99% of compound (10) as measured by HPLC and / or GC analysis.

[0327] Composition Embodiment 69. The composition of any one of Composition Embodiments 5 to 68, comprising about 0.000001% to about 10% of any one or more molecules as measured by HPLC and / or GC analysis.

[0328] Composition Embodiment 70. The composition of Composition Embodiment 69, comprising about 0.000001% to about 5% of any one or more molecules as measured by HPLC and / or GC analysis.

[0329] Composition Embodiment 71. The composition of Composition Embodiment 69, comprising about 0.0001% to about 10% of any one or more molecules as measured by HPLC and / or GC analysis.

[0330] Composition Embodiment 72. The composition of Composition Embodiment 71, comprising about 0.0001% to about 5% of any one or more molecules as measured by HPLC and / or GC analysis.

[0331] Composition Embodiment 72. The composition of composition embodiment 72, comprising about 0.001% to about 3% of any one or more molecules as measured by HPLC and / or GC analysis.

[0332] Composition Embodiment 73. The composition of any one of composition embodiments 5 to 68, wherein the weight ratio of any one or more molecules to compound (10) is 0.000001 to 0.1.

[0333] Composition Embodiment 74. A composition comprising compound (10); and

[0334] (i) about 0.000001% to about 5% of compound (2) based on HPLC analysis;

[0335] (ii) about 0.000001% to about 5% of compound (21) based on HPLC analysis;

[0336] (iii) about 0.000001% to about 5% of compound (25) based on HPLC analysis; and / or

[0337] (iv) about 0.000001% to about 5% of compound (37) based on HPLC analysis.

[0338] Composition Embodiment 75. The composition of composition embodiment 74, comprising about 0.000001% to about 2% of compound (2) based on HPLC analysis.

[0339] Composition Embodiment 76. The composition of composition embodiment 75, comprising about 0.000001% to about 1% of compound (2) based on HPLC analysis.

[0340] Composition Embodiment 77. The composition of composition embodiment 76, comprising about 0.000001% to about 0.5% of compound (2) based on HPLC analysis.

[0341] Composition Embodiment 78. The composition of composition embodiment 77, comprising about 0.000001% to about 0.25% of compound (2) based on HPLC analysis.

[0342] Composition Embodiment 79. The composition of composition embodiment 78, comprising about 0.000001% to about 0.1% of compound (2) based on HPLC analysis.

[0343] Composition Embodiment 80. The composition of Composition Embodiment 76, comprising about 0.001% to about 1% of Compound (2) based on HPLC analysis.

[0344] Composition Embodiment 81. The composition of Composition Embodiment 80, comprising about 0.01% to about 1% of Compound (2) based on HPLC analysis.

[0345] Composition Embodiment 82. The composition of Composition Embodiment 81, comprising about 0.1% to about 1% of Compound (2) based on HPLC analysis.

[0346] Composition Embodiment 83. The composition of any one of Composition Embodiments 74-82, comprising about 0.000001% to about 2% of Compound (21) based on HPLC analysis.

[0347] Composition Embodiment 84. The composition of Composition Embodiment 83, comprising about 0.000001% to about 1% of Compound (21) based on HPLC analysis.

[0348] Composition Embodiment 85. The composition of Composition Embodiment 84, comprising about 0.000001% to about 0.5% of Compound (21) based on HPLC analysis.

[0349] Composition Embodiment 86. The composition of Composition Embodiment 85, comprising about 0.000001% to about 0.25% of Compound (21) based on HPLC analysis.

[0350] Composition Embodiment 87. The composition of Composition Embodiment 86, comprising about 0.000001% to about 0.1% of Compound (21) based on HPLC analysis.

[0351] Composition Embodiment 88. The composition of Composition Embodiment 84, comprising about 0.001% to about 1% of Compound (21) based on HPLC analysis.

[0352] Composition Embodiment 89. The composition of Composition Embodiment 88, comprising about 0.01% to about 1% of Compound (21) based on HPLC analysis.

[0353] Composition Embodiment 90. The composition of Composition Embodiment 89, comprising about 0.1% to about 1% of Compound (21) based on HPLC analysis.

[0354] Composition Embodiment 91. The composition according to any one of Composition Embodiments 74 to 90, comprising about 0.000001% to about 2% of Compound (25) based on HPLC analysis.

[0355] Composition Embodiment 92. The composition according to Composition Embodiment 91, comprising about 0.000001% to about 1% of Compound (25) based on HPLC analysis.

[0356] Composition Embodiment 93. The composition according to Composition Embodiment 92, comprising about 0.000001% to about 0.5% of Compound (25) based on HPLC analysis.

[0357] Composition Embodiment 94. The composition according to Composition Embodiment 93, comprising about 0.000001% to about 0.25% of Compound (25) based on HPLC analysis.

[0358] Composition Embodiment 95. The composition according to Composition Embodiment 94, comprising about 0.000001% to about 0.1% of Compound (25) based on HPLC analysis.

[0359] Composition Embodiment 96. The composition according to Composition Embodiment 92, comprising about 0.001% to about 1% of Compound (25) based on HPLC analysis.

[0360] Composition Embodiment 97. The composition according to Composition Embodiment 96, comprising about 0.01% to about 1% of Compound (25) based on HPLC analysis.

[0361] Composition Embodiment 98. The composition according to Composition Embodiment 97, comprising about 0.1% to about 1% of Compound (25) based on HPLC analysis.

[0362] Composition Embodiment 99. The composition according to any one of Composition Embodiments 74 to 98, comprising about 0.000001% to about 2% of Compound (37) based on HPLC analysis.

[0363] Composition Embodiment 100. The composition according to Composition Embodiment 99, comprising about 0.000001% to about 1% of Compound (37) based on HPLC analysis.

[0364] Composition Embodiment 101. The composition according to Composition Embodiment 100, wherein the composition comprises about 0.000001% to about 0.5% of the compound (37) based on HPLC analysis.

[0365] Composition Embodiment 102. The composition according to Composition Embodiment 101, wherein the composition comprises about 0.000001% to about 0.25% of the compound (37) based on HPLC analysis.

[0366] Composition Embodiment 103. The composition according to Composition Embodiment 102, wherein the composition comprises about 0.000001% to about 0.1% of the compound (37) based on HPLC analysis.

[0367] Composition Embodiment 104. The composition according to Composition Embodiment 100, wherein the composition comprises about 0.001% to about 1% of the compound (37) based on HPLC analysis.

[0368] Composition Embodiment 105. The composition according to Composition Embodiment 104, wherein the composition comprises about 0.01% to about 1% of the compound (37) based on HPLC analysis.

[0369] Composition Embodiment 106. The composition according to Composition Embodiment 105, wherein the composition comprises about 0.1% to about 1% of the compound (37) based on HPLC analysis.

[0370] Composition Embodiment 107. The composition according to any one of Composition Embodiments 74 to 106, wherein the composition comprises about 50% to about 99.9% of the compound (10) based on HPLC analysis.

[0371] Composition Embodiment 108. The composition according to Composition Embodiment 107, wherein the composition comprises about 75% to about 99.9% of the compound (10) based on HPLC analysis.

[0372] Composition Embodiment 109. The composition according to Composition Embodiment 108, wherein the composition comprises about 80% to about 99.9% of the compound (10) based on HPLC analysis.

[0373] Composition Embodiment 110. The composition according to Composition Embodiment 109, wherein the composition comprises about 85% to about 99.9% of the compound (10) based on HPLC analysis.

[0374] Composition Embodiment 111. The composition of Composition Embodiment 110, comprising about 90% to about 99.9% of Compound (10) based on HPLC analysis.

[0375] Composition Embodiment 112. The composition of Composition Embodiment 111, comprising about 95% to about 99.9% of Compound (10) based on HPLC analysis.

[0376] The compositions in this Section II are collectively referred to as “Compositions of the Disclosure” and individually as “Composition of the Disclosure”.

[0377] III. Tire Compositions of the Disclosure

[0378] In another embodiment, the present disclosure provides compositions (collectively referred to as “Tire Compositions of the Disclosure” or individually as “Tire Composition of the Disclosure”) comprising:

[0379] (i) a compound or composition of the present disclosure; and

[0380] (ii) one or more elastomers; or

[0381] (iii) one or more fillers; or

[0382] (iv) one or more rubber chemicals; or

[0383] (v) one or more plasticizers; or

[0384] (vi) one or more second anti-degradants; or

[0385] (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 second anti-degradants.

[0386] In some embodiments, the tire compositions of the present disclosure comprise from about 0.1 wt / wt% to about 99 wt / wt%, for example, from about 15 wt / wt% to about 85 wt / wt%, of a compound or composition of the present disclosure. In some embodiments, the composition comprises from about 0.1 wt / wt% to about 1 wt / wt%, from about 1 wt / wt% to about 5 wt / wt%, from about 1 wt / wt% to about 15 wt / wt%, from about 1 wt / wt% to about 25 wt / wt%, from about 1 wt / wt% to about 35 wt / wt%, from about 1 wt / wt% to about 45 wt / wt%, from about 1 wt / wt% to about 55 wt / wt%, from about 1 wt / wt% to about 65 wt / wt%, from about 1 wt / wt% to about 75 wt / wt%, from about 1 wt / wt% to about 85 wt / wt%, from about 1 wt / wt% to about 95 wt / wt%, from about 5 wt / wt% to about 15 wt / wt%, from about 5 wt / wt% to about 25 wt / wt%, from about 5 wt / wt% to about 35 wt / wt%, from about 5 wt / wt% to about 45 wt / wt%, from about 5 wt / wt% to about 55 wt / wt%, from about 5 wt / wt% to about 65 wt / wt%, from about 5 wt / wt% to about 75 wt / wt%, from about 5 wt / wt% to about 85 wt / wt%, from about 5 wt / wt% to about 95 wt / wt%, from about 15 wt / wt% to about 25 wt / wt%, from about 15 wt / wt% to about 35 wt / wt%, from about 15 wt / wt% to about 45 wt / wt%, from about 15 wt / wt% to about 55 wt / wt%, from about 15 wt / wt% to about 65 wt / wt%, from about 15 wt / wt% to about 75 wt / wt%, from about 15 wt / wt% to about 95 wt / wt%, from about 25 wt / wt% to about 35 wt / wt%, from about 25 wt / wt% to about 45 wt / wt%, from about 25 wt / wt% to about 55 wt / wt%, from about 25 wt / wt% to about 65 wt / wt%, from about 25 wt / wt% to about 75 wt / wt%, from about 25 wt / wt% to about 85 wt / wt%, from about 25 wt / wt% to about 95 wt / wt%, from about 35 wt / wt% to about 45 wt / wt%, from about 35 wt / wt% to about 55 wt / wt%, from about 35 wt / wt% to about 65 wt / wt%, from about 35 wt / wt% to about 75 wt / wt%, from about 35 wt / wt% to about 85 wt / wt%, from about 35 wt / wt% to about 95 wt / wt%, from about 45 wt / wt% to about 55 wt / wt%, from about 45 wt / wt% to about 65 wt / wt%, from about 45 wt / wt% to about 75 wt / wt%, from about 45 wt / wt% to about 85 wt / wt%, from about 45 wt / wt% to about 95 wt / wt%, from about 55 wt / wt% to about 65 wt / wt%, from about 55 wt / wt% to about 75 wt / wt%, from about 55 wt / wt% to about 85 wt / wt%, from about 55 wt / wt% to about 95 wt / wt%, from about 65 wt / wt% to about 75 wt / wt%, from about 65 wt / wt% to about 85 wt / wt%, from about 65 wt / wt% to about 95 wt / wt%, from about 75 wt / wt% to about 85 wt / wt%, from about 75 wt / wt% to about 95 wt / wt%, or from about 85 wt / wt% to about 95 wt / wt% of a compound or composition of the present disclosure.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 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 a compound or composition of the present disclosure.

[0387] In some embodiments, a tire composition of the present disclosure comprises about 50 wt / wt% of a compound or composition of the present disclosure. In some embodiments, the composition comprises about 1 wt / wt%, about 5 wt / wt%, about 10 wt / wt%, about 15 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt% of a compound or composition of the present disclosure.

[0388] In another embodiment, a tire composition of the present disclosure comprises a compound or composition of the present disclosure and one or more elastomers.

[0389] As used herein, the term "elastomer" is a polymer that has viscoelasticity (i.e., has both viscosity and elasticity), 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 the Hevea brasiliensis tree. Non-limiting types of synthetic rubber include unsaturated rubber, saturated rubber, rubber having fluorine and fluoroalkyl or fluoroalkoxy substituents 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 diene rubber (EPDM), and blends thereof. These unsaturated rubbers undergo cyclization and crosslinking reactions that result in the hardening of aged parts. As oxidation occurs, these vulcanized rubbers become hard and eventually brittle products. Partial oxidation of vulcanized rubbers results in a loss of performance in applications such as vehicle tire sidewalls. Saturated rubbers are rubbers that do not contain C=C unsaturation and include, but are not limited to, acrylic rubber (ACM), chlorinated polyethylene (CM), chlorosulfonated polyethylene (CSM), polychloromethyloxirane (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 substituents on the polymer chain (FKM), silicone rubber (Q), and blends thereof.

[0390] In some embodiments, the natural rubber comprises rubber derived from an alternative rubber plant. As used herein, the term "the natural rubber comprises rubber derived from an alternative rubber plant" refers to a natural elastomer that can be obtained from a "non-Hevea brasiliensis" source. In some embodiments, the alternative rubber plant is Parthenium argentatum (guayule) or Taraxacum kok-saghyz (Russian dandelion).

[0391] In some embodiments, the one or more elastomers further comprise recycled rubber. As used herein, the term "recycled rubber" refers to an elastomer that is recovered from waste material such as scrap tires.

[0392] In some embodiments, the tire composition of the present disclosure comprises about 15 wt / wt% to about 99 wt / wt% of one or more elastomers. In some embodiments, the tire composition of the present disclosure comprises about 15 wt / wt% to about 85 wt / wt% of one or more elastomers. In some embodiments, the composition comprises about 1 wt / wt% to about 5 wt / wt%, about 1 wt / wt% to about 15 wt / wt%, about 1 wt / wt% to about 25 wt / wt%, about 1 wt / wt% to about 35 wt / wt%, about 1 wt / wt% to about 45 wt / wt%, about 1 wt / wt% to about 55 wt / wt%, about 1 wt / wt% to about 65 wt / wt%, about 1 wt / wt% to about 75 wt / wt%, about 1 wt / wt% to about 85 wt / wt%, about 1 wt / wt% to about 95 wt / wt%, about 5 wt / wt% to about 15 wt / wt%, about 5 wt / wt% to about 25 wt / wt%, about 5 wt / wt% to about 35 wt / wt%, about 5 wt / wt% to about 45 wt / wt%, about 5 wt / wt% to about 55 wt / wt%, about 5 wt / wt% to about 65 wt / wt%, about 5 wt / wt% to about 75 wt / wt%, about 5 wt / wt% to about 85 wt / wt%, about 5 wt / wt% to about 95 wt / wt%, about 15 wt / wt% to about 25 wt / wt%, about 15 wt / wt% to about 35 wt / wt%, about 15 wt / wt% to about 45 wt / wt%, about 15 wt / wt% to about 55 wt / wt%, about 15 wt / wt% to about 65 wt / wt%, about 15 wt / wt% to about 75 wt / wt%, about 15 wt / wt% to about 95 wt / wt%, about 25 wt / wt% to about 35 wt / wt%, about 25 wt / wt% to about 45 wt / wt%, about 25 wt / wt% to about 55 wt / wt%, about 25 wt / wt% to about 65 wt / wt%, about 25 wt / wt% to about 75 wt / wt%, about 25 wt / wt% to about 85 wt / wt%, about 25 wt / wt% to about 95 wt / wt%, about 35 wt / wt% to about 45 wt / wt%, about 35 wt / wt% to about 55 wt / wt%, about 35 wt / wt% to about 65 wt / wt%, about 35 wt / wt% to about 75 wt / wt%, about 35 wt / wt% to about 85 wt / wt%, about 35 wt / wt% to about 95 wt / wt%, about 45 wt / wt% to about 55 wt / wt%, about 45 wt / wt% to about 65 wt / wt%, about 45 wt / wt% to about 75 wt / wt%, about 45 wt / wt% to about 85 wt / wt%, about 45 wt / wt% to about 95 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 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 elastomers.

[0393] In some embodiments, the tire compositions of the present disclosure comprise about 50 wt / wt% of one or more elastomers. In some embodiments, the compositions comprise about 1 wt / wt%, about 5 wt / wt%, about 10 wt / wt%, about 15 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt% of one or more elastomers.

[0394] As used herein, the term “phr” means parts per hundred parts by weight of rubber. The parts by weight of individual components are based on 100 parts by weight of the total mass of the one or more elastomers present in the composition.

[0395] In some embodiments, the tire composition of the present disclosure comprises about 1 phr to about 5 phr of the compound or composition 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 the compound or composition of the present disclosure.

[0396] In some embodiments, the tire composition of the present disclosure comprises about 3 phr of the compound or composition of the present disclosure. In some embodiments, the composition comprises about 0.01 phr, about 0.1 phr, and 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 the compound or composition of the present disclosure.

[0397] In some embodiments, the tire composition of the present disclosure comprises the compound or composition of the present disclosure and one or more fillers.

[0398] As used herein, the term "filler" is a substance that enhances the elastomeric composition or imparts other properties to the elastomeric composition, including but not limited to expanding the volume of the composition. Non-limiting examples of fillers include carbon black, silica, kaolin, calcium silicate, talc, carbon nanotubes (CNTs), carbon fiber (HCF), graphite, graphene, aluminosilicates, starch, and fibers, and combinations thereof.

[0399] In some embodiments, the filler is derived from a natural source. For example, the silica can be derived from rice hulls.

[0400] In some embodiments, the tire compositions of the present disclosure comprise about 15 wt / wt% to about 85 wt / wt% of one or more fillers. In some embodiments, the compositions comprise about 1 wt / wt% to about 5 wt / wt%, about 1 wt / wt% to about 15 wt / wt%, about 1 wt / wt% to about 25 wt / wt%, about 1 wt / wt% to about 35 wt / wt%, about 1 wt / wt% to about 45 wt / wt%, about 1 wt / wt% to about 55 wt / wt%, about 1 wt / wt% to about 65 wt / wt%, about 1 wt / wt% to about 75 wt / wt%, about 1 wt / wt% to about 85 wt / wt%, about 1 wt / wt% to about 95 wt / wt%, about 5 wt / wt% to about 15 wt / wt%, about 5 wt / wt% to about 25 wt / wt%, about 5 wt / wt% to about 35 wt / wt%, about 5 wt / wt% to about 45 wt / wt%, about 5 wt / wt% to about 55 wt / wt%, about 5 wt / wt% to about 65 wt / wt%, about 5 wt / wt% to about 75 wt / wt%, about 5 wt / wt% to about 85 wt / wt%, about 5 wt / wt% to about 95 wt / wt%, about 15 wt / wt% to about 25 wt / wt%, about 15 wt / wt% to about 35 wt / wt%, about 15 wt / wt% to about 45 wt / wt%, about 15 wt / wt% to about 55 wt / wt%, about 15 wt / wt% to about 65 wt / wt%, about 15 wt / wt% to about 75 wt / wt%, about 15 wt / wt% to about 95 wt / wt%, about 25 wt / wt% to about 35 wt / wt%, about 25 wt / wt% to about 45 wt / wt%, about 25 wt / wt% to about 55 wt / wt%, about 25 wt / wt% to about 65 wt / wt%, about 25 wt / wt% to about 75 wt / wt%, about 25 wt / wt% to about 85 wt / wt%, about 25 wt / wt% to about 95 wt / wt%, about 35 wt / wt% to about 45 wt / wt%, about 35 wt / wt% to about 55 wt / wt%, about 35 wt / wt% to about 65 wt / wt%, about 35 wt / wt% to about 75 wt / wt%, about 35 wt / wt% to about 85 wt / wt%, about 35 wt / wt% to about 95 wt / wt%, about 45 wt / wt% to about 55 wt / wt%, about 45 wt / wt% to about 65 wt / wt%, about 45 wt / wt% to about 75 wt / wt%, about 45 wt / wt% to about 85 wt / wt%, about 45 wt / wt% to about 95 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 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 fillers.

[0401] In some embodiments, the tire compositions of the present disclosure comprise about 50 wt / wt% of one or more fillers. In some embodiments, the compositions comprise about 1 wt / wt%, about 5 wt / wt%, about 10 wt / wt%, about 15 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt% of one or more fillers.

[0402] In some embodiments, the tire compositions of the present disclosure comprise about 30 phr to about 500 phr of one or more fillers. In some embodiments, the compositions comprise 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.

[0403] In some embodiments, the tire compositions of the present disclosure comprise about 300 phr of one or more fillers. In some embodiments, the compositions comprise 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.

[0404] In some embodiments, the tire compositions of the present disclosure comprise a compound or composition 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 the vulcanization of rubber. Rubber chemicals include, but are not limited to, vulcanizing agents, accelerators, activators, and pre-vulcanization inhibitors.

[0405] As used herein, the term “vulcanization” refers to the process by 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 temperatures, depending on the nature of the elastomers, fillers, and rubber chemicals used. The term “curing” is also used in the art to describe this process.

[0406] As used herein, the term “vulcanizing agent” refers to any substance that enables crosslinks to occur between elastomers. Vulcanizing agents can enable crosslinks to occur 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, vulcanizing vegetable oils, greases, and resins. Non-limiting examples of sulfur include octasulfur (S8), cyclododecasulfur (S12), and polymeric sulfur. Non-limiting examples of peroxides include benzoyl peroxide, dicumyl peroxide (DC), 2,5-dimethyl-2,5-di(tert-butylperoxy)-3-hexyne (2,5 Tri), 2,5-dimethyl-2,5-di(tert-butylperoxy)hexane (DDPH), di-(2-tert-butylperoxyisopropyl)benzene (VC), butyl-4,4-di(tert-butylperoxy)valerate (VAL), and 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.

[0407] As used herein, the term “accelerator” refers to any substance that increases the kinetics of vulcanization. In some embodiments, the accelerator enables vulcanization at lower temperatures and / or more efficient use of the vulcanizing agent (e.g., sulfur). Non-limiting examples of accelerators include guanidines, thiazoles, sulfenamides, thiurams, 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-benzothiazole sulfenamide (TBSI). Non-limiting examples of sulfenamides include N-tert-butyl-2-benzothiazole sulfenamide (TBBS), N-cyclohexylbenzothiazole-2-sulfenamide (CBS), dicyclohexyl-2-benzothiazole sulfenamide (DCBS), N-oxydiethylenebenzothiazole sulfenamide (OBTS), N-oxydiethylene thiocarbamyl-N'-oxydiethylene sulfenamide (OTOS), and thiocarbamyl sulfenamide. Non-limiting examples of thiurams include dimethylthiocarbamic acid disulfide peroxide anhydride (thiram), dipentamethylenethiuram tetrasulfide (DPIT), tetrabenzylthiuram disulfide (TBzTD), tetraethylthiuram disulfide (TETD), tetramethylthiuram disulfide (TMTD), and tetramethylthiuram monosulfide (TMTM). Non-limiting examples of dithiocarbamates include zinc dimethyldithiocarbamate (ZDMC), zinc diethyldithiocarbamate (ZDEC), zinc dibutyldithiocarbamate (ZDBC), nickel dibutyldithiocarbamate (NDBC), sodium dibenzyl dithiocarbamate (SBEC), sodium diethyldithiocarbamate (SDEC), tellurium diethyldithiocarbamate (TDEC), and zinc dibenzyl dithiocarbamate (ZEBC).

[0408] 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, forming a chemical complex with the accelerator or 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.

[0409] As used herein, the term "prevulcanization inhibitor" refers to a compound that retards the onset of vulcanization and / or the 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.

[0410] In some embodiments, the tire compositions of the present disclosure comprise about 15 wt / wt% to about 85 wt / wt% of one or more rubber chemicals. In some embodiments, the compositions comprise about 1 wt / wt% to about 5 wt / wt%, about 1 wt / wt% to about 15 wt / wt%, about 1 wt / wt% to about 25 wt / wt%, about 1 wt / wt% to about 35 wt / wt%, about 1 wt / wt% to about 45 wt / wt%, about 1 wt / wt% to about 55 wt / wt%, about 1 wt / wt% to about 65 wt / wt%, about 1 wt / wt% to about 75 wt / wt%, about 1 wt / wt% to about 85 wt / wt%, about 1 wt / wt% to about 95 wt / wt%, about 5 wt / wt% to about 15 wt / wt%, about 5 wt / wt% to about 25 wt / wt%, about 5 wt / wt% to about 35 wt / wt%, about 5 wt / wt% to about 45 wt / wt%, about 5 wt / wt% to about 55 wt / wt%, about 5 wt / wt% to about 65 wt / wt%, about 5 wt / wt% to about 75 wt / wt%, about 5 wt / wt% to about 85 wt / wt%, about 5 wt / wt% to about 95 wt / wt%, about 15 wt / wt% to about 25 wt / wt%, about 15 wt / wt% to about 35 wt / wt%, about 15 wt / wt% to about 45 wt / wt%, about 15 wt / wt% to about 55 wt / wt%, about 15 wt / wt% to about 65 wt / wt%, about 15 wt / wt% to about 75 wt / wt%, about 15 wt / wt% to about 95 wt / wt%, about 25 wt / wt% to about 35 wt / wt%, about 25 wt / wt% to about 45 wt / wt%, about 25 wt / wt% to about 55 wt / wt%, about 25 wt / wt% to about 65 wt / wt%, about 25 wt / wt% to about 75 wt / wt%, about 25 wt / wt% to about 85 wt / wt%, about 25 wt / wt% to about 95 wt / wt%, about 35 wt / wt% to about 45 wt / wt%, about 35 wt / wt% to about 55 wt / wt%, about 35 wt / wt% to about 65 wt / wt%, about 35 wt / wt% to about 75 wt / wt%, about 35 wt / wt% to about 85 wt / wt%, about 35 wt / wt% to about 95 wt / wt%, about 45 wt / wt% to about 55 wt / wt%, about 45 wt / wt% to about 65 wt / wt%, about 45 wt / wt% to about 75 wt / wt%, about 45 wt / wt% to about 85 wt / wt%, about 45 wt / wt% to about 95 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 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.

[0411] In some embodiments, the tire compositions of the present disclosure comprise about 15 wt / wt% of one or more rubber chemicals. 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 rubber chemicals.

[0412] In some embodiments, the tire compositions of the present disclosure comprise about 1 phr to about 20 phr of one or more rubber chemicals. In some embodiments, the compositions comprise 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.

[0413] In some embodiments, the tire compositions of the present disclosure comprise about 10 phr of one or more rubber chemicals. In some embodiments, the compositions comprise 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.

[0414] As used herein, the term “plasticizer” refers to a processing aid used to lower the viscosity, increase the plasticity, and / or expand the volume of a composition. Plasticizers facilitate mixing and formation of a composition comprising an elastomer before the composition is vulcanized. Non-limiting examples of plasticizers include mineral oils (paraffinic, aromatic, or naphthenic), organic esters, resins, waxes, ester plasticizers, and naturally sourced oils, such as soybean oil, vegetable oil, or orange oil.

[0415] In some embodiments, the tire compositions of the present disclosure comprise about 15 wt / wt% to about 85 wt / wt% of one or more plasticizers. In some embodiments, the compositions comprise about 1 wt / wt% to about 5 wt / wt%, about 1 wt / wt% to about 15 wt / wt%, about 1 wt / wt% to about 25 wt / wt%, about 1 wt / wt% to about 35 wt / wt%, about 1 wt / wt% to about 45 wt / wt%, about 1 wt / wt% to about 55 wt / wt%, about 1 wt / wt% to about 65 wt / wt%, about 1 wt / wt% to about 75 wt / wt%, about 1 wt / wt% to about 85 wt / wt%, about 1 wt / wt% to about 95 wt / wt%, about 5 wt / wt% to about 15 wt / wt%, about 5 wt / wt% to about 25 wt / wt%, about 5 wt / wt% to about 35 wt / wt%, about 5 wt / wt% to about 45 wt / wt%, about 5 wt / wt% to about 55 wt / wt%, about 5 wt / wt% to about 65 wt / wt%, about 5 wt / wt% to about 75 wt / wt%, about 5 wt / wt% to about 85 wt / wt%, about 5 wt / wt% to about 95 wt / wt%, about 15 wt / wt% to about 25 wt / wt%, about 15 wt / wt% to about 35 wt / wt%, about 15 wt / wt% to about 45 wt / wt%, about 15 wt / wt% to about 55 wt / wt%, about 15 wt / wt% to about 65 wt / wt%, about 15 wt / wt% to about 75 wt / wt%, about 15 wt / wt% to about 95 wt / wt%, about 25 wt / wt% to about 35 wt / wt%, about 25 wt / wt% to about 45 wt / wt%, about 25 wt / wt% to about 55 wt / wt%, about 25 wt / wt% to about 65 wt / wt%, about 25 wt / wt% to about 75 wt / wt%, about 25 wt / wt% to about 85 wt / wt%, about 25 wt / wt% to about 95 wt / wt%, about 35 wt / wt% to about 45 wt / wt%, about 35 wt / wt% to about 55 wt / wt%, about 35 wt / wt% to about 65 wt / wt%, about 35 wt / wt% to about 75 wt / wt%, about 35 wt / wt% to about 85 wt / wt%, about 35 wt / wt% to about 95 wt / wt%, about 45 wt / wt% to about 55 wt / wt%, about 45 wt / wt% to about 65 wt / wt%, about 45 wt / wt% to about 75 wt / wt%, about 45 wt / wt% to about 85 wt / wt%, about 45 wt / wt% to about 95 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 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.

[0416] In some embodiments, the tire compositions of the present disclosure comprise about 15 wt / wt% of optionally 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.

[0417] In some embodiments, the tire compositions of the present disclosure comprise about 1 phr to about 20 phr of one or more plasticizers, optionally. In some embodiments, the compositions comprise 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.

[0418] In some embodiments, the tire compositions of the present disclosure comprise about 10 phr of one or more plasticizers. In some embodiments, the compositions comprise 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.

[0419] In some embodiments, the tire compositions of the present disclosure comprise a second or even additional anti-degradant further comprising a compound or composition that is not of the present disclosure. In some embodiments, the additional anti-degradant is an antioxidant, a heat stabilizer, a light stabilizer, or a fatigue crack stabilizer. In some embodiments, the second anti-degradant is an anti-ozonant. Non-limiting examples of anti-degradants include para-phenylenediamine (PPD), trimethyl-dihydroquinoline (TMQ), phenols or hindered phenols, alkylated diphenylamine (DPA), diphenylamine-ketone condensates, and natural anti-degradants, quinones, hydroquinones, amines, hindered amines, paraffin or microcrystalline waxes. Non-limiting examples of PPDs include N1-(4-methylpentan-2-yl)-N4-phenylbenzene-1,4-diamine (6PPD), N-(1,4-dimethylpentyl)-N'uiD), 1-phenyl-N4-(propan-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.

[0420] In some embodiments, the tire compositions of the present disclosure comprise about 15 wt / wt% to about 85 wt / wt% of a second anti-degradant. In some embodiments, the compositions comprise about 1 wt / wt% to about 5 wt / wt%, about 1 wt / wt% to about 15 wt / wt%, about 1 wt / wt% to about 25 wt / wt%, about 1 wt / wt% to about 35 wt / wt%, about 1 wt / wt% to about 45 wt / wt%, about 1 wt / wt% to about 55 wt / wt%, about 1 wt / wt% to about 65 wt / wt%, about 1 wt / wt% to about 75 wt / wt%, about 1 wt / wt% to about 85 wt / wt%, about 1 wt / wt% to about 95 wt / wt%, about 5 wt / wt% to about 15 wt / wt%, about 5 wt / wt% to about 25 wt / wt%, about 5 wt / wt% to about 35 wt / wt%, about 5 wt / wt% to about 45 wt / wt%, about 5 wt / wt% to about 55 wt / wt%, about 5 wt / wt% to about 65 wt / wt%, about 5 wt / wt% to about 75 wt / wt%, about 5 wt / wt% to about 85 wt / wt%, about 5 wt / wt% to about 95 wt / wt%, about 15 wt / wt% to about 25 wt / wt%, about 15 wt / wt% to about 35 wt / wt%, about 15 wt / wt% to about 45 wt / wt%, about 15 wt / wt% to about 55 wt / wt%, about 15 wt / wt% to about 65 wt / wt%, about 15 wt / wt% to about 75 wt / wt%, about 15 wt / wt% to about 95 wt / wt%, about 25 wt / wt% to about 35 wt / wt%, about 25 wt / wt% to about 45 wt / wt%, about 25 wt / wt% to about 55 wt / wt%, about 25 wt / wt% to about 65 wt / wt%, about 25 wt / wt% to about 75 wt / wt%, about 25 wt / wt% to about 85 wt / wt%, about 25 wt / wt% to about 95 wt / wt%, about 35 wt / wt% to about 45 wt / wt%, about 35 wt / wt% to about 55 wt / wt%, about 35 wt / wt% to about 65 wt / wt%, about 35 wt / wt% to about 75 wt / wt%, about 35 wt / wt% to about 85 wt / wt%, about 35 wt / wt% to about 95 wt / wt%, about 45 wt / wt% to about 55 wt / wt%, about 45 wt / wt% to about 65 wt / wt%, about 45 wt / wt% to about 75 wt / wt%, about 45 wt / wt% to about 85 wt / wt%, about 45 wt / wt% to about 95 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 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 the second antidegradant.

[0421] In some embodiments, the tire composition of the present disclosure comprises about 15 wt / wt% of the second antidegradant. 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 the second antidegradant.

[0422] In some embodiments, the tire composition of the present disclosure comprises about 1 phr to about 5 phr of the second antidegradant. 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.

[0423] In some embodiments, the tire composition of the present disclosure comprises about 3 phr of the second antidegradant. 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 the second antidegradant.

[0424] In some embodiments, the present disclosure provides a composition comprising a compound or composition of the present disclosure and one or more carriers. As used herein, the term "carrier" refers to a solid that can adsorb a liquid while maintaining 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 having a diameter of less than 500 microns.

[0425] In some embodiments, the composition comprises about 15 wt / wt% to about 85 wt / wt% of one or more carriers. In some embodiments, the composition comprises about 1 wt / wt% to about 5 wt / wt%, about 1 wt / wt% to about 15 wt / wt%, about 1 wt / wt% to about 25 wt / wt%, about 1 wt / wt% to about 35 wt / wt%, about 1 wt / wt% to about 45 wt / wt%, about 1 wt / wt% to about 55 wt / wt%, about 1 wt / wt% to about 65 wt / wt%, about 1 wt / wt% to about 75 wt / wt%, about 1 wt / wt% to about 85 wt / wt%, about 1 wt / wt% to about 95 wt / wt%, about 5 wt / wt% to about 15 wt / wt%, about 5 wt / wt% to about 25 wt / wt%, about 5 wt / wt% to about 35 wt / wt%, about 5 wt / wt% to about 45 wt / wt%, about 5 wt / wt% to about 55 wt / wt%, about 5 wt / wt% to about 65 wt / wt%, about 5 wt / wt% to about 75 wt / wt%, about 5 wt / wt% to about 85 wt / wt%, about 5 wt / wt% to about 95 wt / wt%, about 15 wt / wt% to about 25 wt / wt%, about 15 wt / wt% to about 35 wt / wt%, about 15 wt / wt% to about 45 wt / wt%, about 15 wt / wt% to about 55 wt / wt%, about 15 wt / wt% to about 65 wt / wt%, about 15 wt / wt% to about 75 wt / wt%, about 15 wt / wt% to about 95 wt / wt%, about 25 wt / wt% to about 35 wt / wt%, about 25 wt / wt% to about 45 wt / wt%, about 25 wt / wt% to about 55 wt / wt%, about 25 wt / wt% to about 65 wt / wt%, about 25 wt / wt% to about 75 wt / wt%, about 25 wt / wt% to about 85 wt / wt%, about 25 wt / wt% to about 95 wt / wt%, about 35 wt / wt% to about 45 wt / wt%, about 35 wt / wt% to about 55 wt / wt%, about 35 wt / wt% to about 65 wt / wt%, about 35 wt / wt% to about 75 wt / wt%, about 35 wt / wt% to about 85 wt / wt%, about 35 wt / wt% to about 95 wt / wt%, about 45 wt / wt% to about 55 wt / wt%, about 45 wt / wt% to about 65 wt / wt%, about 45 wt / wt% to about 75 wt / wt%, about 45 wt / wt% to about 85 wt / wt%, about 45 wt / wt% to about 95 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 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 carriers.

[0426] In some embodiments, the composition comprises about 15 wt / wt% of one or more carriers. In some embodiments, the composition comprises about 1 wt / wt%, about 5 wt / wt%, about 10 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt% of one or more carriers.

[0427] In some embodiments, the present disclosure provides the compositions described in Table 9.

[0428] Table 9

[0429]

[0430]

[0431] In some embodiments, the vulcanized tire or other rubber article composition of Table 9 comprises about 0.1 wt / wt%, about 0.2 wt / wt%, about 0.3 wt / wt%, about 0.4 wt / wt%, about 0.5 wt / wt%, about 0.6 wt / wt%, about 0.7 wt / wt%, about 0.8 wt / wt%, about 0.9 wt / wt%, about 1 wt / wt%, about 2 wt / wt%, about 3 wt / wt%, about 4 wt / wt%, about 5 wt / wt%, about 6 wt / wt%, about 7 wt / wt%, about 8 wt / wt%, about 9 wt / wt%, or about 10 wt / wt% of a compound or composition of the present disclosure. In some embodiments, the vulcanized tire or other rubber article composition of Table 9 comprises comprises about 5 wt / wt%, about 10 wt / wt%, about 15 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt% of at least one elastomer.

[0432] In some embodiments, the unvulcanized tire inner component or constituent component or other end use component composition of Table 9 comprises about 0.01 wt / wt%, about 0.02 wt / wt%, about 0.03 wt / wt%, about 0.04 wt / wt%, about 0.05 wt / wt%, about 0.06 wt / wt%, about 0.07 wt / wt%, about 0.08 wt / wt%, about 0.09 wt / wt%, about 0.1 wt / wt%, about 0.2 wt / wt%, about 0.3 wt / wt%, about 0.4 wt / wt%, about 0.5 wt / wt%, about 0.6 wt / wt%, about 0.7 wt / wt%, about 0.8 wt / wt%, about 0.9 wt / wt%, about 1 wt / wt%, about 2 wt / wt%, about 3 wt / wt%, about 4 wt / wt%, about 5 wt / wt%, about 6 wt / wt%, about 7 wt / wt%, about 8 wt / wt%, about 9 wt / wt%, or about 10 wt / wt% of a compound or composition of the present disclosure. In some embodiments, the unvulcanized tire inner component or constituent component or other end use component composition of Table 9 comprises at least one elastomer comprising about 5 wt / wt%, about 10 wt / wt%, about 15 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt%.

[0433] The present disclosure also provides a method for making a composition comprising a compound or composition of the present disclosure and one or more carriers, the method comprising mixing the compound with one or more carriers.

[0434] The present disclosure also provides a lubricant composition comprising a compound or composition of the present disclosure and a lubricant. Non-limiting examples of lubricants include mineral oils, high molecular weight petroleum fractions (such as aromatic, naphthenic, and paraffinic fractions), synthetic oils (such as polyalphaolefins (PAOs)), synthetic esters, polyalkylene glycols (PAGs), phosphate esters, perfluoropolyethers (PFPEs), alkylated naphthalenes (ANs), silicate esters, ionic fluids, and multiple alkylated cyclopentanes (MACs), 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).

[0435] The present disclosure also provides combustible fuel compositions comprising a combustible fuel and a compound or composition of the present disclosure. Non-limiting examples of combustible fuels include gasoline, diesel, kerosene, liquefied petroleum gas, synthetic fuels, and biodiesel.

[0436] The present disclosure also provides fuel additive compositions comprising a fuel additive and a compound or composition of the present disclosure. Non-limiting examples of fuel additives include oxygenates (such as alcohols and ethers), antioxidants, stabilizers, detergents, anti-knock agents, lead scavengers, fuel dyes, viscosity modifiers, and butyl rubber. In some embodiments, the butyl rubber is in the form of polyisobutylene succinimides. In some embodiments, the butyl rubber is added as a detergent to prevent diesel fuel injector fouling.

[0437] IV. Vulcanized Elastomeric Articles

[0438] The present disclosure also provides vulcanized elastomeric articles comprising a compound or composition 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.

[0439] The present disclosure also provides vulcanized elastomeric articles made using a tire composition of the present disclosure.

[0440] In some embodiments, the vulcanized elastomeric article is a tire. In some embodiments, the tire is a passenger vehicle tire, a light truck tire, a heavy truck or bus tire, a motorcycle tire, an agricultural tire, a bulldozer tire, an aircraft tire, or a racing tire.

[0441] 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 bottom tread, or a tread.

[0442] In some embodiments, 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 crash pad, a hose, a conveyor belt, or a floor.

[0443] In some embodiments, the present disclosure provides a vehicle comprising a vulcanized elastomeric article comprising a compound or composition of the present disclosure.

[0444] V. Methods

[0445] The present disclosure also provides methods for making a vulcanized elastomeric article, the method comprising:

[0446] (a) forming a tire composition of the present disclosure into a shaped form; and

[0447] (b) curing the shaped form,

[0448] to provide a vulcanized elastomeric article.

[0449] 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.

[0450] 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.

[0451] The present disclosure also provides a method for retreading a tire, the method comprising:

[0452] (a) applying a tire composition of the present disclosure to a tire;

[0453] (b) disposing a pre-vulcanized tread around the tire;

[0454] (c) disposing a curing envelope around the tire; and

[0455] (d) vulcanizing the tire.

[0456] In another embodiment, the present disclosure provides a method for preparing a composition comprising compound (10), or a salt or solvate thereof.

[0457] In another embodiment, the present disclosure provides a method for preparing a composition comprising compound (10), or a salt or solvate thereof, and compound (2), compound (4), and / or compound (11), the method comprising reacting 4-aminodiphenylamine with acetone, 2,2-dimethoxypropane, or isopropylidene acetone in the presence of a strong acid (e.g., hydrochloric acid).

[0458] The present disclosure provides the following specific method embodiments.

[0459] Methodic embodiment 1. A method for making a composition according to any one of composition embodiments 1 to 112 (see above), the method comprising reacting a composition comprising 4-amino diphenylamine with acetone, 2,2-dimethoxypropane, diacetone alcohol, or isopropylidene acetone in the presence of a catalyst.

[0460] Methodic embodiment 2. The method according to methodic embodiment 1, wherein the catalyst is a homogeneous catalyst.

[0461] Methodic embodiment 3. The method according to methodic embodiment 2, wherein the homogeneous catalyst is a Lewis acid, a Bronsted acid, a base, a halogen, a halogen donor, or a combination thereof.

[0462] Methodic embodiment 4. The method according to methodic embodiment 2, wherein the homogeneous catalyst is selected from the group consisting of iodine, pyridinium perbromide, bromine, bismuth(III) trifluoromethanesulfonate, zinc(II) trifluoromethanesulfonate, hydrobromic acid, magnesium(II) bromide, aluminum(III) chloride, p-toluenesulfonic acid monohydrate, N-bromosuccinimide, copper(II) bromide, copper(II) chloride, methanesulfonic acid, benzenesulfonic acid, boron trifluoride diethyl etherate, boron trifluoride dihydrate, hydrochloric acid, copper(II) trifluoromethanesulfonate, iron(III) chloride, magnesium(II) chloride, copper(I) iodide, and zinc(II) chloride, or a salt or solvate thereof.

[0463] Methodic embodiment 5. The method according to methodic embodiment 4, wherein the homogeneous catalyst is selected from the group consisting of pyridinium perbromide, magnesium(II) bromide, magnesium(II) bromide hexahydrate, and aluminum(III) chloride.

[0464] Methodic embodiment 6. The method according to methodic embodiment 1, wherein the catalyst is a heterogeneous catalyst.

[0465] Methodic embodiment 7. The method according to methodic embodiment 6, wherein the heterogeneous catalyst is an acid-treated resin, a solid-supported acid, a composite catalyst, a solid acid, or a base catalyst.

[0466] Methodic embodiment 8. The method according to methodic embodiment 7, wherein the acid-treated resin is a polyfluorinated sulfonic acid resin, a strongly acidic sulfonic acid exchange resin (Amberlyst 15), a macroporous strongly acidic ion exchange resin, a strongly acidic ion exchange resin, a solid acidic ion exchange resin (NRW150), a sieved strongly acidic ion exchange resin, or a strongly acidic ion exchange resin (A2 type acid resin).

[0467] Method embodiment 9. The method of method embodiment 7, wherein the solid supported acid is micro-meso-macroporous zeolite catalyst H-Y-MMM, strong acidity molecular sieve H-MCM-22, organic protic acid supported by graphene oxide, organic protic acid supported by zeolite, small pore size zeolite, heterogeneous acidic silica catalyst, Zn 2 + Sn 2+ and Cu 2+ exchanged phosphotungstic acid (TPA), tonsil active earth (acid treated bentonite), alumina, titania, zirconia, niobia, silica-alumina, sulfated zirconia, tungstated zirconia, p-toluenesulfonic acid (p-TSA) / ZnCl2or WO3 / activated carbon / SO3H.

[0468] Method embodiment 10. The method of method embodiment 7, wherein the composite catalyst is zirconium-doped titania composite oxide catalyst, H2SO4-MoO3-TiO2 solid superacid, or p-toluenesulfonic acid / iodine.

[0469] Method embodiment 11. The method of method embodiment 7, wherein the solid acid is a heteropoly acid or a metal-organic framework.

[0470] Method embodiment 12. The method of method embodiment 7, wherein the base catalyst is ZrO2 / MgO.

[0471] Method embodiment 13. The method of any one of method embodiments 1 to 12, comprising reacting a composition comprising 4-amino diphenylamine with acetone.

[0472] Method embodiment 14. The method of any one of method embodiments 1 to 12, comprising reacting a composition comprising 4-amino diphenylamine with 2,2-dimethoxypropane.

[0473] Method embodiment 15. The method of any one of method embodiments 1 to 12, comprising reacting a composition comprising 4-amino diphenylamine with diacetone alcohol.

[0474] Method embodiment 16. The method of any one of method embodiments 1 to 12, comprising reacting a composition comprising 4-amino diphenylamine with isopropylidene acetone.

[0475] VI. Kits

[0476] The present disclosure also provides kits comprising a compound or composition of the present disclosure or a tire composition of the present disclosure packaged, for example, in a container that facilitates the use of the compound or composition to practice the processes and / or methods of the present disclosure. In some embodiments, the kit comprises a tire composition of the present disclosure and instructions for using the composition in a vulcanizable elastomer composition. In some embodiments, the kit comprises a tire composition of the present disclosure 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 vessel, with a label on the container), or included in a kit that describes the composition and its proper use.

[0477] VII. DEFINITIONS

[0478] As used herein, the term "weight ratio" refers to the mass of one compound in a composition divided by the mass of another compound. For example, in a composition comprising 1 gram of compound (2) and 1000 grams of compound (10), the weight ratio of compound (2) to compound (10) is 0.001. In a composition comprising 10 grams of compound (2) and 100 grams of compound (10), the weight ratio of compound (2) to compound (10) is 0.1.

[0479] In some embodiments, the compounds of the present disclosure comprise a mixture of E and Z stereoisomers, as illustrated for compound (4) below:

[0480]

[0481] In some embodiments, the compounds of the present disclosure comprise a mixture comprising E and Z stereoisomers, wherein the E:Z ratio is from 500:1 to 1:500. In some embodiments, the E:Z ratio is from 100:1 to 1:100. In some embodiments, the E:Z ratio is from 10:1 to 1:10. In some embodiments, the E:Z ratio is from 5:1 to 1:5. In some embodiments, the E:Z ratio is from 3:1 to 1:3. In some embodiments, the E:Z ratio is from 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.

[0482] In some embodiments, the compounds of the present disclosure comprise only the E stereoisomer, i.e., no detectable amount of the Z stereoisomer as measured by HPLC.

[0483] In some embodiments, the compounds of the present disclosure contain only the Z stereoisomer, that is, no detectable amount of the E stereoisomer as measured by HPLC.

[0484] As used herein, the term "about" includes ±10% of the indicated number. Thus, "about 10" means 9 to 11.

[0485] The use of the word "comprise" and its variations is intended to be synonymous with the word "include" and its variations. The use of the words "comprise" and "comprising" and the like are not intended to exclude other additives, components, integers or steps. It is also to be understood that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. The use of the word "a" or "an" is intended to mean "one or more" unless otherwise indicated.

[0486] Salts and solvates (e.g., hydrates) of the compounds of the present disclosure can also be used in the methods disclosed herein.

[0487] 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, or separately, by reacting the compound 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 used to form salts include inorganic acids (such as nitric, boric, hydrochloric, hydrobromic, sulfuric, and phosphoric acids) and organic acids (such as oxalic, maleic, succinic, tartaric, 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, tartrates, gluconates, methanesulfonates, ethanedisulfonates, benzenesulfonates, and p-toluenesulfonates. Additionally, available aminos in the compounds of the present disclosure can be quaternized using 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 foregoing, any reference to a compound of the present disclosure herein is intended to include the compound of the present disclosure as well as salts, hydrates, or solvates thereof.

[0488] The present disclosure encompasses the preparation and use of solvates of the compounds of the present disclosure. As used herein, the term “solvate” refers to a combination or physical association of a compound of the present disclosure with solvent molecules, e.g., disolvate, monosolvate, or hemisolvate, wherein the ratio of solvent molecules to compounds of the present disclosure is about 2:1, about 1:1, or about 1:2, respectively. Such physical associations involve varying degrees of ionization 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” encompasses both solution-phase and isolatable solvates. The compounds of the present disclosure can exist in solvated forms, such as with water, methanol, and ethanol, and the present disclosure is intended to include both solvated and unsolvated forms of the compounds of the present disclosure.

[0489] One type of solvate is a hydrate. "Hydrate" is related to a specific subset of solvates where 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 solvates of fluconazole with ethyl acetate and with water. Similar preparations of solvates, hemisolvates, hydrates, and the like are described by van Tonder et al., AAPS Pharm. Sci. Tech., 5(1): Article 12 (2004) and by A. L. Bingham et al., Chem. Commun. 603-604 (2001). A typical, non-limiting method of preparing a solvate involves dissolving the compound or composition of the present disclosure in a desired solvent (organic solvent, water, or mixtures thereof) at a temperature above 20 °C to about 25 °C, then allowing the solution to cool at a rate sufficient to form crystals, and isolating the crystals by known methods (e.g., filtration). Analytical techniques such as infrared spectroscopy can be used to confirm the presence of a solvent in the solvate crystal.

[0490] The use of the terms "a" and "an" and "the" and similar referents in the context of describing the disclosure (especially in the context of the following claims) are to be construed to cover both the singular and the plural, unless otherwise indicated herein or clearly contradicted by context. Recitation of a range of values herein is merely intended to serve as a shorthand method of referring individually to each separate value falling within the range, unless otherwise indicated herein, and each separate value is incorporated into the specification as if it were individually recited herein. The use of any and all examples, or exemplary language (e.g., "such as") provided herein, is intended merely to better illuminate the disclosure and does not pose a limitation on the scope of the disclosure unless otherwise claimed. No language in the specification should be construed as indicating any non-claimed element as essential to the practice of the disclosure.

[0491] As used herein, the term "and / or" shall be taken to mean either the conjunctive or the disjunctive sense, i.e., "and / or" shall be taken to mean either "and" or "or," or both, in each instance in which it is used. Likewise, the term "and / or" as used in a phrase such as "A and / or B" is intended to cover, in separate embodiments, A alone, B alone, or A and B together. Similarly, the term "and / or" as used in a phrase such as "A, B, and / or C" is intended to cover, in separate embodiments, A alone, B alone, C alone, A and B together, A and C together, B and C together, or A and B and C together.

[0492] As used herein, the term "wt / wt%" refers to the mass of one component in a composition or blend (e.g., a composition comprising a compound of the disclosure and one or more elastomers); or a composition of the disclosure and one or more fillers; or a blend comprising two or more elastomers, etc., divided by the combined mass of all components in the composition or blend multiplied by 100. For example, in a composition comprising 1 kg of a compound, 1 kg of natural rubber, and 2 kg of synthetic rubber, the wt / wt% of the compound of the disclosure is 25 wt / wt% (1 kg / 4 kg = 0.25 x 100 = 25 wt / wt%). In a composition comprising 1 kg of a compound and 1 kg of carbon black, the wt / wt% of the compound of the disclosure is 50 wt / wt% (1 kg / 2 kg = 0.20 x 100 = 50 wt / wt%). In a composition comprising 1 kg of a compound, 1 kg of natural rubber, 2 kg of synthetic rubber, and 1 kg of carbon black, the wt / wt% of the compound of the disclosure is 20 wt / wt% (1 kg / 5 kg = 0.20 x 100 = 20 wt / wt%). In a blend of one or more elastomers comprising 20 kg of natural rubber and 30 kg of synthetic rubber, the wt / wt% of the natural rubber is 40 wt / wt% (20 kg / 50 kg = 0.40 x 100 = 40 wt / wt%).

[0493] As used herein, the term "masterbatch" refers to a composition comprising at least one elastomer and a compound or composition of the present disclosure. In some embodiments, the masterbatch comprises about 5 wt% to about 95 wt% of at least one elastomer and about 5 wt% to about 95 wt% of a compound or composition of the present disclosure. In some embodiments, the masterbatch comprises about 5 wt% to about 10 wt% to about 15 wt% to about 20 wt% to about 25 wt% to about 30 wt% to about 35 wt% to about 40 wt% to about 45 wt% to about 50 wt% to about 55 wt% to about 60 wt% to about 65 wt% to about 70 wt% to about 75 wt% to about 80 wt% to about 85 wt% to about 90 wt% to about 95 ...5 wt% to In some embodiments, the masterbatch comprises at least one elastomer in the form of about 5 wt / wt%, about 10 wt / wt%, about 15 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt%.

[0494] As used herein, the term "premix" refers to a composition comprising a compound or composition of the present disclosure and at least one additional component (e.g., a filler, rubber chemical, plasticizer, additional anti-degradation agent, or a combination thereof). In some embodiments, the premix does not contain an elastomer. In some embodiments, the premix comprises about 5 wt% to about 95 wt% of a compound or composition of the present disclosure and about 5 wt% to about 95 wt% of at least one additional component (e.g., a filler, rubber chemical, plasticizer, additional anti-degradation agent, or a combination thereof). In some embodiments, the premix comprises about 5 wt / wt%, about 10 wt / wt%, about 15 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt% of the compounds of this disclosure. In some embodiments, the premix comprises about 5 wt / wt%, about 10 wt / wt%, about 15 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt%, of at least one additional component (e.g., filler, rubber chemicals, plasticizer, additional anti-degradation agent, or combinations thereof).

[0495] As used herein, the term "one or more" is intended to mean the presence of at least one component of a relevant category, such as one or more elastomers, and in some embodiments, the presence of more than one component. 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.

[0496] VIII. Specific Implementation Plans

[0497] The present disclosure provides the following specific embodiments. Compound structures are provided in Table 1.

[0498] Embodiment 1. Compound (9), or a salt or solvate thereof.

[0499] Embodiment 2. Compound (10), or a salt or solvate thereof.

[0500] Embodiment 3. A composition comprising a compound according to Embodiment 1 or 2 and Compound (1), wherein the composition comprises about 0.0001% to about 10% of Compound (1), e.g., about 0.001% to about 10%, about 0.01% to about 10%, about 0.1% to about 10%, about 0.0001% to about 5%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.0001% to about 1%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of Compound (1), as measured by HPLC analysis.

[0501] Embodiment 4. A composition comprising a compound according to Embodiment 1 or 2 and Compound (2), wherein the composition comprises about 0.0001% to about 10% of Compound (2), e.g., about 0.001% to about 10%, about 0.01% to about 10%, about 0.1% to about 10%, about 0.0001% to about 5%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.0001% to about 1%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of Compound (2), as measured by HPLC analysis.

[0502] Embodiment 5. A composition comprising a compound according to Embodiment 1 or 2 and Compound (3), wherein the composition comprises about 0.001% to about 10% of Compound (3), e.g., about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of Compound (3), as measured by HPLC analysis.

[0503] Embodiment 6. A composition comprising a compound according to Embodiment 1 or 2 and Compound (4), wherein the composition comprises about 0.001% to about 10% of Compound (4), e.g., about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of Compound (4) as determined by HPLC analysis.

[0504] Embodiment 7. A composition comprising a compound according to Embodiment 1 or 2 and Compound (5), wherein the composition comprises about 0.001% to about 10% of Compound (5), e.g., about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of Compound (5) as determined by HPLC analysis.

[0505] Embodiment 8. A composition comprising a compound according to Embodiment 1 or 2 and Compound (6), wherein the composition comprises about 0.001% to about 10% of Compound (6), e.g., about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of Compound (6) as determined by HPLC analysis.

[0506] Embodiment 9. A composition comprising a compound according to Embodiment 1 or 2 and Compound (7), wherein the composition comprises about 0.001% to about 10% of Compound (7), e.g., about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of Compound (7) as determined by HPLC analysis.

[0507] Embodiment 10. A composition comprising a compound according to Embodiment 1 or 2 and compound (8), wherein the composition comprises about 0.001% to about 10% of compound (8), e.g., about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of compound (8), as determined by HPLC analysis.

[0508] Embodiment 11. A composition comprising a compound according to Embodiment 1 or 2 and compound (11A), wherein the composition comprises about 0.001% to about 10% of compound (11A), e.g., about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of compound (11A), as determined by HPLC analysis.

[0509] Embodiment 12. A composition comprising a compound according to Embodiment 1 or 2 and compound (12), wherein the composition comprises about 0.001% to about 10% of compound (12), e.g., about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of compound (12), as determined by HPLC analysis.

[0510] Embodiment 13. A composition comprising a compound according to Embodiment 1 or 2 and compound (13), wherein the composition comprises about 0.001% to about 10% of compound (13), e.g., about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of compound (13), as determined by HPLC analysis.

[0511] Embodiment 14. A composition comprising a compound according to Embodiment 1 or 2 and Compound (14), wherein the composition comprises about 0.001% to about 10% of Compound (14), e.g., about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of Compound (14) as determined by HPLC analysis.

[0512] Embodiment 15. A composition comprising a compound according to Embodiment 1 or 2 and Compound (15), wherein the composition comprises about 0.001% to about 10% of Compound (15), e.g., about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of Compound (15) as determined by HPLC analysis.

[0513] Embodiment 16. A composition comprising a compound according to Embodiment 1 or 2 and Compound (16), wherein the composition comprises about 0.001% to about 10% of Compound (16), e.g., about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of Compound (16) as determined by HPLC analysis.

[0514] Embodiment 17. A composition comprising a compound according to Embodiment 1 or 2 and Compound (17), wherein the composition comprises about 0.001% to about 10% of Compound (17), e.g., about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of Compound (17) as determined by HPLC analysis.

[0515] Embodiment 18. A composition comprising a compound according to Embodiment 1 or 2 and compound (18), wherein the composition comprises about 0.001% to about 10% of compound (18) as determined by HPLC analysis, for example, about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of compound (18).

[0516] Embodiment 19. A composition comprising a compound according to Embodiment 1 or 2 and compound (19), wherein the composition comprises about 0.001% to about 10% of compound (19) as determined by HPLC analysis, for example, about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of compound (19).

[0517] Embodiment 20. A composition comprising a compound according to Embodiment 1 or 2 and compound (20A), wherein the composition comprises about 0.001% to about 20% of compound (20A) as determined by HPLC analysis, for example, about 0.01% to about 20%, about 0.1% to about 20%, about 0.001% to about 15%, about 0.01% to about 15%, about 0.1% to about 15%, about 0.001% to about 10%, about 0.01% to about 10%, about 0.01% to about 15%, about 0.5% to about 15%, or about 1% to 15% of compound (20).

[0518] Embodiment 21. A composition comprising compound (10); and:

[0519] (i) compound (2), wherein the composition comprises about 0.0001% to about 10% of compound (2) as determined by HPLC analysis, for example, about 0.01% to about 10%, about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of compound (2); and / or

[0520] (ii) Compound (4), wherein the composition comprises from about 0.001% to about 10% of Compound (4) as measured by HPLC analysis, for example, from about 0.01% to about 10%, from about 0.1% to about 10%, from about 0.001% to about 5%, from about 0.01% to about 5%, from about 0.1% to about 5%, from about 0.001% to about 1%, from about 0.01% to about 1%, from about 0.01% to about 0.5%, from about 0.05% to about 0.5%, or from about 0.1% to 0.5% of Compound (4); and / or

[0521] (iii) Compound (11A) or Compound (11B), wherein the composition comprises from about 0.001% to about 10% of Compound (11A) or Compound (11B) as measured by HPLC analysis, for example, from about 0.01% to about 10%, from about 0.1% to about 10%, from about 0.001% to about 5%, from about 0.01% to about 5%, from about 0.1% to about 5%, from about 0.001% to about 1%, from about 0.01% to about 1%, from about 0.01% to about 0.5%, from about 0.05% to about 0.5%, or from about 0.1% to 0.5% of Compound (11A) or Compound (11B); and / or

[0522] (iv) Compound (20A) or Compound (20B), wherein the composition comprises from about 0.001% to about 10% of Compound (20A) or Compound (20B) as measured by HPLC analysis, for example, from about 0.01% to about 10%, from about 0.1% to about 10%, from about 0.001% to about 5%, from about 0.01% to about 5%, from about 0.1% to about 5%, from about 0.001% to about 1%, from about 0.01% to about 1%, from about 0.01% to about 0.5%, from about 0.05% to about 0.5%, or from about 0.1% to 0.5% of Compound (20A) or Compound (20B).

[0523] Embodiment 22. Compound (3).

[0524] Embodiment 23. Compound (4).

[0525] Embodiment 24. A composition comprising a compound according to Embodiment 22 or 23.

[0526] Embodiment 25. A composition comprising a composition according to any one of Embodiments 3 to 21, 24, 118 to 125, 127, 129, 130, 133, or 134, or a compound according to Embodiment 22, 23, 126, 128, 131, or 132; and:

[0527] (i) one or more elastomers; or

[0528] (ii) one or more fillers; or

[0529] (iii) one or more rubber chemicals; or

[0530] (iv) one or more plasticizers; or

[0531] (v) one or more second anti-degradants; or

[0532] (vi) 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 second anti-degradants.

[0533] Embodiment 26. The composition of claim 25, wherein the composition comprises one or more elastomers.

[0534] Embodiment 27. The composition of claim 26, wherein the composition comprises from about 15 wt / wt% to about 85 wt / wt% of the composition of (i) and from about 15 wt / wt% to about 85 wt / wt% of one or more elastomers.

[0535] Embodiment 28. The composition of any one of embodiments 25 to 27, wherein the one or more elastomers comprise natural rubber (NR).

[0536] Embodiment 29. The composition of embodiment 28, wherein the one or more elastomers comprise from about 5 wt / wt% to about 80 wt / wt% natural rubber (NR).

[0537] Embodiment 30. The composition of embodiment 28 or 29, wherein the natural rubber comprises rubber derived from an alternative rubber plant.

[0538] Embodiment 31. The composition of embodiment 30, wherein the alternative rubber plant is Paraguayan guayule (Paraguayan guayule) or Russian dandelion (Russian dandelion).

[0539] Embodiment 32. The composition of any one of embodiments 26 to 31, wherein the one or more elastomers comprise synthetic rubber.

[0540] Embodiment 33. The composition of embodiment 32, wherein the synthetic rubber comprises unsaturated rubber, saturated rubber, rubber with fluorine and fluoroalkyl or fluoroalkoxy substituents on the polymer chain (FKM), silicone rubber (Q), or a blend thereof.

[0541] Embodiment 34. The composition of embodiment 33, 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 diene rubber (EPDM), or a blend thereof.

[0542] Embodiment 35. The composition of embodiment 34, wherein the unsaturated rubber comprises styrene butadiene rubber (SBR).

[0543] Embodiment 36. The composition of embodiment 35, wherein the one or more elastomers comprise about 5 wt / wt% to about 80 wt / wt% of styrene butadiene rubber (SBR).

[0544] Embodiment 37. The composition of any one of embodiments 34 to 36, wherein the unsaturated rubber comprises polybutadiene rubber (BR).

[0545] Embodiment 38. The composition of embodiment 37, wherein the one or more elastomers comprise about 5 wt / wt% to about 80 wt / wt% of polybutadiene rubber (BR).

[0546] Embodiment 39. The composition of any one of embodiments 34 to 38, wherein the unsaturated rubber comprises butyl rubber (IIR).

[0547] Embodiment 40. The composition of embodiment 39, wherein the one or more elastomers comprise about 1 wt / wt% to about 30 wt / wt% of butyl rubber (IIR).

[0548] Embodiment 41. The composition of any one of embodiments 33 to 40, wherein the saturated rubber comprises acrylic rubber (ACM), chlorinated polyethylene (CM), chlorosulfonated polyethylene (CSM), polychloromethyloxirane (CO), ethylene-ethyl acrylate copolymer (EAM), epichlorohydrin rubber (ECO), ethylene propylene rubber (EPM), ethylene vinyl acetate copolymer (EVM), or a blend thereof.

[0549] Embodiment 42. The composition of any one of embodiments 35 to 41, wherein the one or more elastomers further comprise a recycled rubber.

[0550] Embodiment 43. The composition of any one of embodiments 35 to 42, wherein the composition comprises about 0.1 phr to about 10 phr of the composition of (i).

[0551] Embodiment 44. The composition of Embodiment 43, wherein the composition comprises about 0.5 phr to about 5 phr of the composition of (i).

[0552] Embodiment 45. The composition of Embodiment 44, wherein the composition comprises about 1 phr to about 5 phr of the composition of (i).

[0553] Embodiment 46. The composition of any one of Embodiments 25 to 45, wherein the composition comprises one or more fillers.

[0554] Embodiment 47. The composition of Embodiment 46, wherein the composition comprises about 15 wt / wt% to about 85 wt / wt% of the composition of (i) and about 15 wt / wt% to about 85 wt / wt% of one or more fillers.

[0555] Embodiment 48. The composition of Embodiment 46 or 47, wherein the composition comprises about 30 phr to about 500 phr of one or more fillers.

[0556] Embodiment 49. The composition of any one of Embodiments 46 to 48, wherein the one or more fillers comprise carbon black, silica, kaolin, calcium silicate, talc, carbon nanotubes (CNTs), carbon fiber (HCF), graphite, graphene, aluminosilicate, starch, fibers, or combinations thereof.

[0557] Embodiment 50. The composition of Embodiment 49, wherein the one or more fillers comprise silica.

[0558] Embodiment 51. The composition of Embodiment 50, wherein the silica is derived from rice hulls.

[0559] Embodiment 52. The composition of any one of Embodiments 46 to 51, wherein the one or more fillers comprise carbon black.

[0560] Embodiment 53. The composition of any one of Embodiments 25 to 52, wherein the composition comprises one or more rubber chemicals.

[0561] Embodiment 54. The composition of Embodiment 53, wherein the composition comprises about 15 wt / wt% to about 85 wt / wt% of the composition of (i) and about 15 wt / wt% to about 85 wt / wt% of one or more rubber chemicals.

[0562] phr to about 30 phr of one or more rubber chemicals.

[0563] Embodiment 56. The composition of Embodiment 55, wherein the composition comprises about 1 phr to about 20 phr of one or more rubber chemicals.

[0564] Embodiment 57. The composition of any one of Embodiments 53-56, wherein the one or more rubber chemicals comprises one or more vulcanizing agents, one or more accelerators, one or more activators, one or more antiprecipitation agents, or a combination thereof.

[0565] Embodiment 58. The composition of Embodiment 57, wherein the one or more rubber chemicals comprises one or more vulcanizing agents.

[0566] Embodiment 59. The composition of Embodiment 58, wherein the one or more vulcanizing agents comprises sulfur, a peroxide, a resin, or a combination thereof.

[0567] Embodiment 60. The composition of Embodiment 59, wherein the sulfur is octasulfur (S8), cyclododecasulfur (S 12 ), polymeric sulfur, or a combination thereof.

[0568] Embodiment 61. The composition of Embodiment 59, wherein the peroxide is benzoyl peroxide, dicumyl peroxide (DC), 2,5-dimethyl-2,5-di(tert-butylperoxy)-3-hexyne (2,5 Tri), 2,5-dimethyl-2,5-di(tert-butylperoxy)hexane (DDPH), di-(2-tert-butylperoxyisopropyl)benzene (VC), butyl-4,4-di(tert-butylperoxy) valerate (VAL), 1,1-di(tert-butylperoxy)-3,3,5-trimethylcyclohexane (TMC), or a combination thereof.

[0569] Embodiment 62. The composition of Embodiment 59, wherein the resin is a bonding resin.

[0570] Embodiment 63. The composition of any one of Embodiments 57-62, wherein the one or more rubber chemicals comprises one or more accelerators.

[0571] Embodiment 64. The composition of Embodiment 63, wherein the one or more accelerators comprises guanidine, thiazole, sulfenamide, dithiocarbamate, xanthate, thiophosphate, or a combination thereof.

[0572] Embodiment 65. The composition of embodiment 64, wherein the guanidine is diphenylguanidine (DPG).

[0573] Embodiment 66. The composition of embodiment 64, wherein the thiazole comprises 2- mercaptobenzothiazole (MBT), 2-mercaptobenzothiazole zinc (ZMBT), mercaptobenzothiazole disulfide (MBTS), N-tert-butyl-2-benzothiazole sulfenamide (TBSI), or a combination thereof.

[0574] Embodiment 67. The composition of embodiment 64, wherein the sulfenamide comprises N-tert- butyl-2-benzothiazole sulfenamide (TBBS), N-cyclohexylbenzothiazole-2-sulfenamide (CBS), dicyclohexyl-2-benzothiazole sulfenamide (DCBS), N-oxydiethylenebenzothiazole sulfenamide (OBTS), N-oxydiethylene thiocarbamoyl-N'-oxydiethylene sulfenamide (OTOS), thiocarbamoyl sulfenamide, or a combination thereof.

[0575] Embodiment 68. The composition of embodiment 64, wherein the thiuram is disulfobenzoyl disulfide (thiuram disulfide), dipentamethylene thiuram tetrasulfide (DPIT), tetrabenzylthiuram disulfide (TBzTD), tetraethylthiuram disulfide (TETD), tetramethylthiuram disulfide (TMTD), tetramethylthiuram monosulfide (TMTM), or a combination thereof.

[0576] Embodiment 69. The composition of embodiment 64, wherein the dithiocarbamate comprises zinc dimethyldithiocarbamate (ZDMC), zinc diethyldithiocarbamate (ZDEC), zinc dibutyldithiocarbamate (ZDBC), nickel dibutyldithiocarbamate (NDBC), sodium dibenzyl dithiocarbamate (SBEC), sodium diethyldithiocarbamate (SDEC), tellurium diethyldithiocarbamate (TDEC), zinc dibenzyl dithiocarbamate (ZEBC), or a combination thereof.

[0577] Embodiment 70. The composition of any one of embodiments 57-69, wherein the one or more rubber chemicals comprise one or more activators.

[0578] Embodiment 71. The composition of embodiment 70, wherein the one or more activators comprise a metal oxide, an acid, a metal complex, or a combination thereof.

[0579] Embodiment 72. The composition of embodiment 71, wherein the metal oxide comprises zinc oxide, magnesium oxide, lead oxide, or a combination thereof.

[0580] Embodiment 73. The composition of embodiment 72, wherein the acid comprises stearic acid, lauric acid, or a combination thereof.

[0581] Embodiment 74. The composition of embodiment 72, wherein the metal complex comprises zinc ethylhexanoate.

[0582] Embodiment 75. The composition of any one of embodiments 57-74, wherein the one or more rubber chemicals comprise one or more pre-vulcanization inhibitors.

[0583] Embodiment 76. The composition of embodiment 75, wherein the one or more pre-vulcanization inhibitors comprise N-(cyclohexylthio)phthalimide (CTP), benzoic anhydride, salicylic anhydride, phthalic anhydride, or a combination thereof.

[0584] Embodiment 77. The composition of any one of embodiments 25-76, wherein the composition comprises one or more plasticizers.

[0585] Embodiment 78. The composition of embodiment 77, wherein the composition comprises from about 15 wt / wt% to about 85 wt / wt% of the composition of (i) and from about 15 wt / wt% to about 85 wt / wt% of the one or more plasticizers.

[0586] Embodiment 79. The composition of embodiment 77 or 78, wherein the composition comprises from about 0.1 phr to about 30 phr of the one or more plasticizers.

[0587] Embodiment 80. The composition of embodiment 79, wherein the composition comprises from about 1 phr to about 20 phr of the one or more plasticizers.

[0588] Embodiment 81. The composition of any one of embodiments 77-80, wherein the one or more plasticizers comprise mineral oil, organic ester, resin, wax, ester plasticizer, naturally derived oil, or a combination thereof.

[0589] Embodiment 82. The composition of embodiment 81, wherein the mineral oil is naphthenic oil, paraffinic oil, or aromatic oil.

[0590] Embodiment 83. The composition of embodiment 81, wherein the naturally derived oil is soybean oil, vegetable oil, or orange oil.

[0591] Embodiment 84. The composition of any one of embodiments 25-83, wherein the composition further comprises a second anti-degradant.

[0592] Embodiment 85. The composition of Embodiment 84, wherein the composition comprises from about 15 wt / wt% to about 85 wt / wt% of the composition of (i) and from about 15 wt / wt% to about 85 wt / wt% of one or more second antidegradants.

[0593] Embodiment 86. The composition of Embodiment 84 or 85, wherein the one or more second antidegradants are present in an amount from about 0.001 phr to about 10 phr.

[0594] Embodiment 87. The composition of Embodiment 86, wherein the one or more second antidegradants are present in an amount from about 0.1 phr to about 5 phr.

[0595] Embodiment 88. The composition of Embodiment 87, wherein the one or more second antidegradants are present in an amount from about 0.5 phr to about 5 phr.

[0596] Embodiment 89. The composition of Embodiment 88, wherein the one or more second antidegradants are present in an amount from about 1 phr to about 5 phr.

[0597] Embodiment 90. The composition of any one of Embodiments 84-89, wherein the one or more second antidegradants are antioxidants.

[0598] Embodiment 91. The composition of any one of Embodiments 84-89, wherein the one or more second antidegradants are antiozonants.

[0599] Embodiment 92. The composition of any one of Embodiments 84-91, wherein the one or more second antidegradants are p-phenylenediamine (PPD), trimethyldihydroquinoline (TMQ), phenolics, alkylated diphenylamine (DPA), or diphenylamine-ketone condensates.

[0600] Embodiment 93. The composition of Embodiment 92, wherein the PPD is N 1 -(4-methylpentan-2-yl)-N 4 -phenylbenzene-1,4-diamine (6PPD), N-(1,4-dimethylpentyl)-N'-phenyl-p-phenylenediamine (7PPD), 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).

[0601] Embodiment 94. The composition of Embodiment 93, wherein the PPD is 6PPD.

[0602] Embodiment 95. The composition of Embodiment 92, wherein the TMQ is 2,2,4-trimethyl-1,2-dihydroquinoline or oligomers or polymers thereof.

[0603] Embodiment 96. A vulcanized elastomeric article comprising the composition of any one of Embodiments 2595.

[0604] Embodiment 97. A vulcanized elastomeric article prepared using the composition of any one of Embodiments 25 to 95.

[0605] Embodiment 98. The vulcanized elastomeric article of Embodiment 96 or 97, wherein the vulcanized elastomeric article is a tire.

[0606] Embodiment 99. The vulcanized elastomeric article of Embodiment 98, 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.

[0607] Embodiment 100. The vulcanized elastomeric article of Embodiment 96 or 97, wherein the vulcanized elastomeric article is a component of a tire.

[0608] Embodiment 101. The vulcanized elastomeric article of Embodiment 100, wherein the component is a bead, a belt, a body ply layer, an inner liner, a sidewall, a bottom tread, or a tread.

[0609] Embodiment 102. The vulcanized elastomeric article of Embodiment 96 or 97, 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 crash pad, a hose, a conveyor belt, or a floor.

[0610] Embodiment 103. A method for preparing a vulcanized elastomeric article, the method comprising:

[0611] (a) forming the composition of any one of Embodiments 25 to 95 into a shaped form; and

[0612] (b) vulcanizing the shaped form,

[0613] to provide a vulcanized elastomeric article.

[0614] Embodiment 104. The method of embodiment 103, wherein the vulcanization is conducted at an average temperature of from about 120 °C to about 180 °C.

[0615] Embodiment 105. The method of embodiment 104, wherein the vulcanization is conducted at an average temperature of from about 140 °C to about 160 °C.

[0616] Embodiment 106. The method of any one of embodiments 103 to 105, wherein the vulcanized elastomeric article is a tire.

[0617] Embodiment 107. The method of embodiment 106, 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.

[0618] Embodiment 108. The method of any one of embodiments 103 to 107, wherein the vulcanized elastomeric article is a component of a tire.

[0619] Embodiment 109. The method of embodiment 108, wherein the component is a bead, a belt, a body ply layer, an inner liner, a sidewall, a bottom tread, or a tread.

[0620] Embodiment 110. The method of any one of embodiments 103 to 105, 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 crash pad, a hose, a conveyor belt, or a floor.

[0621] Embodiment 111. A lubricant composition comprising a lubricant and the composition of any one of embodiments 25 to 95.

[0622] Embodiment 112. A combustible fuel composition comprising a combustible fuel and the composition of any one of embodiments 25 to 95.

[0623] Embodiment 113. A fuel additive composition comprising a fuel additive and the composition of any one of embodiments 25 to 95.

[0624] Embodiment 114. A method for retreading a tire, the method comprising:

[0625] (a) applying the composition of any one of embodiments 25 to 95 to a tire;

[0626] (b) disposing a pre-vulcanized tread around the tire;

[0627] (c) disposing a cured envelope around the tire; and

[0628] (d) vulcanizing the tire.

[0629] Embodiment 115. A kit comprising a composition according to any one of embodiments 25 to 95 and instructions for using the composition in a vulcanizable elastomer composition.

[0630] Embodiment 116. A kit comprising a composition according to any one of embodiments 25 to 95 and instructions for using the composition to make a vulcanized elastomer article.

[0631] Embodiment 117. A method for making a composition according to any one of embodiments 3 to 21, the method comprising reacting 4-aminodiphenylamine with acetone, 2,2-dimethoxypropane, or isopropylidene acetone in the presence of a strong acid (e.g., hydrochloric acid).

[0632] Embodiment 118. A composition comprising a compound according to embodiment 1 or 2 and compound (21), wherein the composition comprises from about 0.0001% to about 10% of compound (21) as measured by HPLC analysis, for example, from about 0.001% to about 10%, 0.01% to about 10%, from about 0.1% to about 10%, from about 0.0001% to about 5%, from about 0.001% to about 5%, from about 0.01% to about 5%, from about 0.1% to about 5%, from about 0.0001% to about 1%, from about 0.001% to about 1%, from about 0.01% to about 1%, from about 0.1% to about 1%, from about 0.5% to about 10%, or from about 1% to 10% of compound (21).

[0633] Embodiment 119. A composition comprising compound (10); and:

[0634] (i) compound (2), wherein the composition comprises from about 0.0001% to about 10% of compound (2) as measured by HPLC analysis, for example, from about 0.01% to about 10%, from about 0.01% to about 10%, from about 0.1% to about 10%, from about 0.001% to about 5%, from about 0.01% to about 5%, from about 0.1% to about 5%, from about 0.001% to about 1%, from about 0.01% to about 1%, from about 0.01% to about 0.5%, from about 0.05% to about 0.5%, or from about 0.1% to 0.5% of compound (2); and / or

[0635] (ii) Compound (4), wherein the composition comprises about 0.001% to about 10% of Compound (4) as measured by HPLC analysis, for example, about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of Compound (4); and / or

[0636] (iii) Compound (11A) or Compound (11B), wherein the composition comprises about 0.001% to about 10% of Compound (11A) or Compound (11B) as measured by HPLC analysis, for example, about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of Compound (11A) or Compound (11B); and / or

[0637] (iv) Compound (20A) or Compound (20B), wherein the composition comprises about 0.001% to about 10% of Compound (20A) or Compound (20B) as measured by HPLC analysis, for example, about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of Compound (20A) or Compound (20B); and / or

[0638] (v) Compound (21), wherein the composition comprises about 0.0001% to about 10% of Compound (21) as measured by HPLC analysis, for example, about 0.01% to about 10%, about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of Compound (21).

[0639] Embodiment 120. A composition comprising compound (10) and compound (2), wherein the composition comprises about 0.0001% to about 10% of compound (2) as determined by HPLC analysis, for example, about 0.01% to about 10%, about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of compound (2).

[0640] Embodiment 121. A composition comprising compound (10) and compound (21), wherein the composition comprises about 0.0001% to about 10% of compound (21) as determined by HPLC analysis, for example, about 0.01% to about 10%, about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of compound (21).

[0641] Embodiment 122. A composition comprising compound (10); and:

[0642] (i) compound (2), wherein the composition comprises about 0.0001% to about 10% of compound (2) as determined by HPLC analysis, for example, about 0.01% to about 10%, about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of compound (2); and

[0643] (ii) compound (21), wherein the composition comprises about 0.0001% to about 10% of compound (21) as determined by HPLC analysis, for example, about 0.01% to about 10%, about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of compound (21).

[0644] Embodiment 123. A composition comprising compound (10) and compound (2), wherein the composition comprises about 85% to about 99.5% of compound (10) as measured by HPLC analysis, for example, about 90% to about 99.5% or about 95% to about 99% of compound (10); and about 0.0001% to about 10% of compound (2) as measured by HPLC analysis, for example, about 0.01% to about 10%, about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of compound (2); and about 85% to about 99.5% of compound (10), for example, about 90% to about 99.5% or about 95% to about 99% of compound (10).

[0645] Embodiment 124. A composition comprising compound (10) and compound (21), wherein the composition comprises about 85% to about 99.5% of compound (10) as measured by HPLC analysis, for example, about 90% to about 99.5% or about 95% to about 99% of compound (10); and about 0.0001% to about 10% of compound (21) as measured by HPLC analysis, for example, about 0.01% to about 10%, about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of compound (21).

[0646] Embodiment 125. A composition comprising compound (10), compound (2), and compound (21), wherein the composition comprises about 85% to about 99.5% of compound (10), e.g., about 90% to about 99.5% or about 95% to about 99% of compound (10), as determined by HPLC analysis; about 0.0001% to about 10% of compound (2), e.g., about 0.01% to about 10%, about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of compound (2), as determined by HPLC analysis; and about 0.0001% to about 10% of compound (21), e.g., about 0.01% to about 10%, about 0.01% to about 10%, about 0.1% to about 10%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.01% to about 0.5%, about 0.05% to about 0.5%, or about 0.1% to 0.5% of compound (21), as determined by HPLC analysis.

[0647] Embodiment 126. Compound (21).

[0648] Embodiment 127. A composition comprising the compound of Embodiment 126.

[0649] Embodiment 128. Compound (22).

[0650] Embodiment 129. A composition comprising the compound of Embodiment 128.

[0651] Embodiment 130. A composition comprising the compound of Embodiment 1 or 2 and compound (22), wherein the composition comprises about 0.0001% to about 10% of compound (22), e.g., about 0.001% to about 10%, 0.01% to about 10%, about 0.1% to about 10%, about 0.0001% to about 5%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.0001% to about 1%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.1% to about 1%, about 0.5% to about 10%, or about 1% to 10% of compound (22), as determined by HPLC analysis.

[0652] Embodiment 131. Compound (23).

[0653] Embodiment 132. Compound (24).

[0654] Embodiment 133. A composition comprising a compound according to Embodiment 1 or 2 and compound (23), wherein the composition comprises from about 0.0001% to about 10% of compound (23) as determined by HPLC analysis, for example, from about 0.001% to about 10%, 0.01% to about 10%, from about 0.1% to about 10%, from about 0.0001% to about 5%, from about 0.001% to about 5%, from about 0.01% to about 5%, from about 0.1% to about 5%, from about 0.0001% to about 1%, from about 0.001% to about 1%, from about 0.01% to about 1%, from about 0.1% to about 1%, from about 0.5% to about 10%, or from about 1% to 10% of compound (23).

[0655] Embodiment 134. A composition comprising a compound according to Embodiment 1 or 2 and compound (24), wherein the composition comprises from about 0.0001% to about 10% of compound (24) as determined by HPLC analysis, for example, from about 0.001% to about 10%, 0.01% to about 10%, from about 0.1% to about 10%, from about 0.0001% to about 5%, from about 0.001% to about 5%, from about 0.01% to about 5%, from about 0.1% to about 5%, from about 0.0001% to about 1%, from about 0.001% to about 1%, from about 0.01% to about 1%, from about 0.1% to about 1%, from about 0.5% to about 10%, or from about 1% to 10% of compound (24).

[0656] Embodiment 135. A composition comprising a compound according to Embodiment 1 or 2 and compound (25), wherein the composition comprises from about 0.0001% to about 10% of compound (25) as determined by HPLC analysis, for example, from about 0.001% to about 10%, 0.01% to about 10%, from about 0.1% to about 10%, from about 0.0001% to about 5%, from about 0.001% to about 5%, from about 0.01% to about 5%, from about 0.1% to about 5%, from about 0.0001% to about 1%, from about 0.001% to about 1%, from about 0.01% to about 1%, from about 0.1% to about 1%, from about 0.5% to about 10%, or from about 1% to 10% of compound (25).

[0657] Embodiment 136. A composition comprising a compound according to Embodiment 1 or 2 and compound (37), wherein the composition comprises about 0.0001% to about 10% of compound (37), e.g., about 0.001% to about 10%, 0.01% to about 10%, about 0.1% to about 10%, about 0.0001% to about 5%, about 0.001% to about 5%, about 0.01% to about 5%, about 0.1% to about 5%, about 0.0001% to about 1%, about 0.001% to about 1%, about 0.01% to about 1%, about 0.1% to about 1%, about 0.5% to about 10%, or about 1% to 10% of compound (37), as measured by HPLC analysis.

[0658] The present disclosure provides the following specific embodiments. Compound structures are provided in Table 1.

[0659] Embodiment 1. A compound of Formula (I):

[0660]

[0661] or a salt or solvate thereof, wherein represents a single or double bond.

[0662] Embodiment 2. The compound according to Embodiment 1, wherein the compound of Formula (I) is compound (1).

[0663] Embodiment 3. The compound according to Embodiment 1, wherein the compound of Formula (I) is compound (2).

[0664] Embodiment 4. A composition comprising a compound according to any one of Embodiments 1-3, or a salt or solvate thereof.

[0665] Embodiment 5. A compound of Formula (II):

[0666]

[0667] or a salt or solvate thereof, wherein represents a single or double bond.

[0668] Embodiment 6. The compound according to Embodiment 5, wherein the compound of Formula (II) is compound (3).

[0669] Embodiment 7. The compound according to Embodiment 5, wherein the compound of Formula (II) is compound (4).

[0670] Embodiment 8. A composition comprising a compound according to any one of Embodiments 5 to 7, or a salt or solvate thereof.

[0671] Embodiment 9. A compound of Formula (III):

[0672]

[0673] or a salt or solvate thereof, wherein represents a single or double bond.

[0674] Embodiment 10. The compound according to Embodiment 9, wherein the compound of Formula (III) is Compound (5).

[0675] Embodiment 11. The compound according to Embodiment 9, wherein the compound of Formula (III) is Compound (6).

[0676] Embodiment 12. A composition comprising a compound according to any one of Embodiments 9 to 11, or a salt or solvate thereof.

[0677] Embodiment 13. A compound which is Compound (21), or a salt or solvate thereof.

[0678] Embodiment 14. A composition comprising a compound according to Embodiment 13, or a salt or solvate thereof.

[0679] Embodiment 15. A compound which is Compound (23), or a salt or solvate thereof.

[0680] Embodiment 16. A composition comprising a compound according to Embodiment 15, or a salt or solvate thereof.

[0681] Embodiment 17. A compound which is Compound (24), or a salt or solvate thereof.

[0682] Embodiment 18. A composition comprising a compound according to Embodiment 17, or a salt or solvate thereof.

[0683] Embodiment 19. A composition comprising a compound of Formula (IV):

[0684]

[0685] or a salt or solvate thereof, and:

[0686] (a) a compound of Formula (I):

[0687]

[0688] or a salt or solvate thereof; or:

[0689] (b) a compound of Formula (II):

[0690]

[0691] or a salt or solvate thereof; or

[0692] (c) a compound of Formula (III):

[0693]

[0694] or a salt or solvate thereof; or

[0695] (d) compound (7) or a salt or solvate thereof; or

[0696] (e) compound (8) or a salt or solvate thereof; or

[0697] (f) compound (11A) or compound (11B), or a salt or solvate thereof; or

[0698] (g) compound (20A) or compound (20B), or a salt or solvate thereof; or

[0699] (h) compound 21 or a salt or solvate thereof; or

[0700] (i) compound (22) or a salt or solvate thereof; or

[0701] (j) compound (23) or a salt or solvate thereof; or

[0702] (k) compound (24) or a salt or solvate thereof; or

[0703] (l) a combination of: Formula (I) or a salt or solvate thereof; Formula (II) or a salt or solvate thereof; Formula (III) or a salt or solvate thereof; compound (7) or a salt or solvate thereof; compound (8) or a salt or solvate thereof; compound (11A) or compound (11B), or a salt or solvate thereof; compound (20A) or compound (20B), or a salt or solvate thereof; and / or compound (21) or a salt or solvate thereof; compound (22) or a salt or solvate thereof; compound (23) or a salt or solvate thereof; and / or compound (24) or a salt or solvate thereof,

[0704] wherein represents a single or double bond.

[0705] Embodiment 20. The composition of Embodiment 19, comprising a compound of Formula (IV), or a salt or solvate thereof, and a compound of Formula (I), or a salt or solvate thereof.

[0706] Embodiment 21. The composition of Embodiment 19 or 20, comprising about 0.1% to about 10% of Formula (I) as measured by high performance liquid chromatography (HPLC) analysis.

[0707] Embodiment 22. The composition of Embodiment 19 or 20, wherein the weight ratio of Formula (I) to Formula (IV) is 0.001 to 0.1.

[0708] Embodiment 23. The composition of any one of Embodiments 19-33, comprising a compound of Formula (IV), or a salt or solvate thereof, and a compound of Formula (II), or a salt or solvate thereof.

[0709] Embodiment 24. The composition of any one of Embodiments 19-23, comprising about 0.1% to about 10% of Formula (II) as measured by HPLC analysis.

[0710] Embodiment 25. The composition of any one of Embodiments 19-23, wherein the weight ratio of Formula (II) to Formula (IV) is 0.001 to 0.1.

[0711] Embodiment 26. The composition of any one of Embodiments 19-25, comprising a compound of Formula (IV), or a salt or solvate thereof, and a compound of Formula (III), or a salt or solvate thereof.

[0712] Embodiment 27. The composition of any one of Embodiments 19-26, comprising about 0.1% to about 10% of Formula (III) as measured by HPLC analysis.

[0713] Embodiment 28. The composition of any one of Embodiments 19-26, wherein the weight ratio of Formula (IIII) to Formula (IV) is 0.001 to 0.1.

[0714] Embodiment 29. The composition of any one of Embodiments 19-28, comprising a compound of Formula (IV), or a salt or solvate thereof, and compound (7), or a salt or solvate thereof.

[0715] Embodiment 30. The composition of any one of embodiments 19-29, comprising about 0.1% to about 10% of compound (7) as measured by HPLC analysis.

[0716] Embodiment 31. The composition of any one of embodiments 19-29, wherein the weight ratio of compound (7) to formula (IV) is 0.001 to 0.1.

[0717] Embodiment 32. The composition of any one of embodiments 19-31, comprising a compound of formula (IV), or a salt or solvate thereof, and compound (11), or a salt or solvate thereof.

[0718] Embodiment 33. The composition of any one of embodiments 19-32, comprising about 0.001% to about 10% of compound (8) as measured by HPLC analysis.

[0719] Embodiment 34. The composition of any one of embodiments 19-32, wherein the weight ratio of compound (8) to formula (IV) is 0.001 to 0.1.

[0720] Embodiment 35. The composition of any one of embodiments 19-34, comprising about 0.001% to about 10% of compound (11A) or compound (11B) as measured by HPLC analysis.

[0721] Embodiment 36. The composition of any one of embodiments 19-34, wherein the weight ratio of compound (11A) or compound (11B) to formula (IV) is 0.001 to 0.1.

[0722] Embodiment 37. The composition of any one of embodiments 19-36, comprising a compound of formula (IV), or a salt or solvate thereof, and compound (21), or a salt or solvate thereof.

[0723] Embodiment 38. The composition of any one of embodiments 19-37, comprising about 0.1% to about 10% of compound (21) as measured by HPLC analysis.

[0724] Embodiment 39. The composition of any one of embodiments 19-37, wherein the weight ratio of compound (21) to formula (IV) is 0.001 to 0.1.

[0725] Embodiment No. 40. The composition of any one of embodiments No. 19 to No. 39, comprising a compound of Formula (IV), or a salt or solvate thereof, and compound (23), or a salt or solvate thereof.

[0726] Embodiment No. 41. The composition of any one of embodiments No. 19 to No. 40, comprising about 0.1% to about 10% of compound (23), as determined by HPLC analysis.

[0727] Embodiment No. 42. The composition of any one of embodiments No. 19 to No. 40, wherein the weight ratio of compound (23) to Formula (IV) is 0.001 to 0.1.

[0728] Embodiment No. 43. The composition of any one of embodiments No. 19 to No. 42, comprising a compound of Formula (IV), or a salt or solvate thereof, and compound (24), or a salt or solvate thereof.

[0729] Embodiment No. 44. The composition of any one of embodiments No. 19 to No. 43, comprising about 0.01% to about 10% of compound (23), as determined by HPLC analysis.

[0730] Embodiment No. 45. The composition of any one of embodiments No. 19 to No. 43, wherein the weight ratio of compound (23) to Formula (IV) is 0.0001 to 0.1.

[0731] Embodiment No. 46. The composition of any one of embodiments No. 19 to No. 45, wherein the compound of Formula (IV) is compound (9).

[0732] Embodiment No. 47. The composition of any one of embodiments No. 19 to No. 47, wherein the compound of Formula (IV) is compound (10).

[0733] Embodiment No. 48. A composition comprising compound (10); and

[0734] (i) about 0.001% to about 10% of compound (2), as determined by HPLC analysis; and / or

[0735] (ii) about 0.001% to about 10% of compound (4), as determined by HPLC analysis, and / or

[0736] (iii) about 0.001% to about 10% of compound (11A) or compound (11B), as determined by HPLC analysis, and / or

[0737] (iv) about 0.001% to about 20% of compound (20A) or compound (20B), as determined by HPLC analysis, and / or

[0738] (v) about 0.001% to about 10% of compound (21), as determined by HPLC analysis, and / or (vi) about 0.0001% to about 3% of compound (23), as determined by HPLC analysis, and / or (vii) about 0.0001% to about 3% of compound (24), as determined by HPLC analysis.

[0739] 49thembodiment. The composition of the 48thembodiment, comprising compound (10) and about 0.001% to about 10% of compound (2), as determined by HPLC analysis.

[0740] 50thembodiment. The composition of the 48thor 49thembodiment, comprising compound (10) and about 0.01% to about 1% of compound (2), as determined by HPLC analysis.

[0741] 51stembodiment. The composition of the 8thor 49thembodiment, comprising compound (10) and about 0.03% to about 3% of compound (2), as determined by HPLC analysis.

[0742] 52ndembodiment. The composition of the 8thembodiment, comprising compound (10) and about 0.001% to about 10% of compound (21), as determined by HPLC analysis.

[0743] 53rdembodiment. The composition of any one of the 48thto 52ndembodiments, comprising compound (10) and about 0.01% to about 1% of compound (21), as determined by HPLC analysis.

[0744] 54thembodiment. The composition of any one of the 48thto 52ndembodiments, comprising compound (10) and about 0.03% to about 3% of compound (21), as determined by HPLC analysis.

[0745] 55thembodiment. The composition of any one of the 48thto 52ndembodiments, comprising about 0.02% to about 2% of compound (11A) or compound (11B), as determined by HPLC analysis.

[0746] 56thembodiment. The composition of any one of the 48thto 52ndembodiments, comprising about 1% to about 20% of compound (20A) or compound (20B), as determined by HPLC analysis.

[0747] Embodiment No. 57. The composition of any one of Embodiments No. 48-56, comprising about 90% to about 99% of compound (10) as measured by HPLC analysis.

[0748] Embodiment No. 58. The composition of any one of Embodiments No. 4, 8, 12, 14, 16, 18-57, further comprising:

[0749] (i) one or more elastomers; or

[0750] (ii) one or more fillers; or

[0751] (iii) one or more rubber chemicals; or

[0752] (iv) one or more plasticizers; or

[0753] (v) one or more second anti-degradants; or

[0754] (vi) 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 second anti-degradants.

[0755] Embodiment No. 59. A vulcanized elastomeric article comprising the composition of Embodiment No. 58.

[0756] Embodiment No. 60. A vehicle comprising the vulcanized elastomeric article of Embodiment No. 59.

[0757] Embodiment No. 61. A kit comprising the composition of Embodiment No. 58 and instructions for using the composition to prepare a vulcanized elastomeric article.

[0758] Embodiment No. 62. A method for preparing the composition of any one of Embodiments No. 4, 8, 14, 16, 18-45, comprising reacting a composition comprising 4-aminodiphenylamine with acetone, 2,2-dimethoxypropane, or isopropylidene acetone in the presence of a strong acid.

[0759] Embodiment No. 63. A composition comprising the compound of Embodiments No. 2, 3, 6, 7, 10, 11, 13, 15, and 17, and:

[0760] (i) one or more elastomers; or

[0761] (ii) one or more fillers; or

[0762] (iii) one or more rubber chemicals; or

[0763] (iv) one or more plasticizers; or

[0764] (v) one or more second anti-degradants; or

[0765] (vi) 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 second anti-degradants.

[0766] 64. A vulcanized elastomeric article comprising the composition of embodiment 63.

[0767] 65. A vehicle comprising the vulcanized elastomeric article of embodiment 64.

[0768] 66. A kit comprising the composition of embodiment 65 and instructions for using the composition to prepare a vulcanized elastomeric article.

[0769] Example

[0770] Example 1

[0771] Reaction of 4-aminodiphenylamine with acetone

[0772] A 500-mL kettle reactor was charged with 184.0 g of 4-aminodiphenylamine (1.0 mole; 99.2% purity) and 8.3 mL of concentrated hydrochloric acid (0.1 mole, 37%, d = 1.18) catalyst, the kettle reactor was equipped with a mechanical stirrer, temperature control, an addition funnel, a nitrogen inlet, and a condenser with a receiver. While stirring under nitrogen, heat to 95 °C. Feed 440 mL of acetone (6.0 moles, technical grade, d = 0.784) from the addition funnel to the stirred reactor over 4.5 hours at 95 °C under nitrogen. Transfer 265 mL of acetone collected in the receiver to the addition funnel and feed it to the reactor over 1.5 hours while stirring at 95 °C under nitrogen. Neutralize the reaction mass with 60 mL of 15% aqueous sodium carbonate solution. Cool to room temperature. Transfer the contents of the reactor in 2 batches to a separatory funnel with 200 mL of toluene and 50 mL of water. Separate the layers and discard the aqueous layer. Remove the toluene by rotary evaporation. Recover 212 g of 37% 6-anilino-2,2,4-trimethyl-1,2-dihydroquinoline (i.e., compound (10)) and 54% of unreacted 4-aminodiphenylamine (“4-ADPA”) starting material by area percent HPLC. Isolate the 4-ADPA from compound (10) by preparing a crude solution of approximately 20 g of the reaction mixture in 30 mL of chloroform, charge it onto a sintered glass filter (13.3 cm diameter, 2000-mL size) prepared with 350-400 g of silica gel 60, elute with 3 L to 4 L of additional chloroform in 500-mL batches, collect the clean filtrate (check by thin layer chromatography for the effectiveness of 4-ADPA isolation), and remove the volatiles by rotary evaporation. Analysis of the final material purified by the silica gel column filter showed 95.3% of compound (10) and other unexpected molecules (i.e., byproducts) as measured by HPLC. See Figure 1 Table 1 and Table 2. The HPLC peak at 8.7 minutes has not been identified as compound (11A), compound (11B), compound (20A), or compound (20B).

[0773] Table 2

[0774]

[0775] Method 1. HPLC Analysis

[0776] Chromatograms were obtained using an Agilent 1260 Infinity II series HPLC system equipped with a Poroshell 120 column (EC-C18 4.6 x 50 mm, 2.7 pm) held at 25 °C with a 5 pL injection volume. The UV absorption of the effluent was measured using a diode array detector at multiple wavelengths in the range of 200 nm to 450 nm (2 nm step size). The wavelength 260 nm was used to determine the peak area percentage of the individual components. Analytes can be reliably detected at 0.5 ppm or above. The molecular weight of each peak observed in the chromatogram was identified by MS coupled to the LC-UV system (using a single quadrupole mass selective detector in positive mode for atmospheric pressure chemical ionization). The source parameters were set as follows: gas and vaporizer temperatures were 300 °C and 200 °C, respectively, gas flow was 5.0 L / min, and the nebulizer pressure was 15 PSI. The mobile phase (1 mL / min flow rate) consisted of 5 mmol / L ammonium formate in water (solvent A) and acetonitrile (solvent B) using the following gradient shown in Table 3.

[0777] Table 3

[0778] Time (min) Solvent A (%) Solvent B (%) 0.00 70 30 0.50 70 30 9.00 5 95 16.00 5 95 18.00 70 30 20.00 70 30

[0779] Method 2: HPLC-UV / MS

[0780] Chromatograms were obtained using an Agilent 1260 Infinity II series HPLC system equipped with an Agilent Poroshell 120 column (EC-C18 4.6 x 100 mm, 2.7 pm, PN: 695975-902) held at 25 °C with a 5 pL injection volume. The UV absorption of the effluent was measured using a diode array detector at multiple wavelengths in the range of 200 nm to 450 nm (2 nm step size). The wavelength 290 nm (bw = 20) can be used to determine the peak area percentage of the individual components. The molecular weight of each peak observed in the chromatogram was identified by MS coupled to the LC-UV system (using an Agilent InfinityLab LC / MSD G6125C single quadrupole mass selective detector in APCI+ mode with a fragmentation voltage of 100 V). Compounds were detected as the protonated form of the parent ion [M+1] + . The source parameters were set as follows: gas and vaporizer temperatures were 300 °C and 200 °C, respectively, gas flow was 5.0 L / min, and the nebulizer pressure was 15 PSI. For selected ion monitoring (SIM) detection, the mass spectrometer was set to monitor the selected compounds at m / z = [M+1] +The response intensity at the time. For SIM detection of compounds (2), (21), (23) and (25), the mass spectrometer was set to m / z = 265 amu, 225 amu and 279 amu, respectively. The mobile phase (1 mL / min flow rate) consisted of 75 mM aqueous formic acid and 5 mM aqueous ammonium formate buffer solution (solvent D) and acetonitrile (solvent B) using the following gradient shown in Table 4.

[0781] Table 4

[0782]

[0783]

[0784] To minimize interference from high concentration compound (10), during acquisition, during the elution time of compound (10) when using SIM, a split valve was used to divert the eluent from the MS detector to waste.

[0785] To determine the experimental limit of detection, LOD, or lower limit of the working calibration range, two stock solutions of compound (21) were prepared at concentrations of 470 ppm (pg / ml) and 958 ppm (pg / ml). A 10:1 serial dilution was applied to each stock solution until concentrations of 4.70 parts per billion (ppb) and 0.958 ppb, respectively, were achieved. Standards with concentrations between 4.70 ppm and 0.958 ppb (a total of eight standards) were injected using Method 2, and a linear calibration with offset (ignoring the origin) was used to evaluate the calibration range. The lower limit of the working range was determined by the lowest concentration standard with a relative percent residual within + / - 20%. For molecule (21), the LOD was determined to be 9.58 parts per billion with a residual of -19.3%.

[0786] Method 3: GC-MS

[0787] Chromatograms were obtained using a Thermo Fisher Trace 1310 gas chromatograph with ISQ 7000 single quadrupole mass spectrometer for detection. One microliter of sample solution was injected into the split inlet using an AI 1310 autosampler with a split flow of 15 ml / min and a purge flow of 5 ml / min while maintaining an inlet temperature of 250 °C. Helium was used as the carrier gas at a constant flow rate of 1 ml / min and an Agilent VF-5ms capillary column (15 m x 0.25 mm x 1 pm) was used for the stationary phase. An initial oven temperature of 35 °C was held for one minute before ramping up to 240 °C at 15 °C / min. The oven was held at 240 °C for 3 minutes before ramping up to 300 °C at 8 °C / min and held isothermally at this temperature for 20 minutes, resulting in a total method time of 45.2 minutes. The mass spectrometer transfer line temperature and ion source temperature were both 300 °C. Total ion chromatograms were collected from 40-550 amu (0.1 second dwell time) using electron impact (El) ionization mode for general identification, while specific analytes of interest were quantitatively analyzed using targeted mass ranges with the same ionization mode and parameters. The targeted mass range depends on the analyte and is selected from the most abundant ions in the spectrum produced from the above conditions. The selected ion range for compound (21) was 208-210 amu, for compounds (23) and (25) was 262-265 amu, and for compound (2) was 248-250 amu. The method was calibrated with purified external standards diluted to multiple levels (typically between 50 ppb and 5000 ppb, but the range can vary depending on the concentration of the analyte observed). Chromeleon CDS was used for spectral and quantitative analysis.

[0788] To estimate the limit of experimental detection, LOD, or lower limit of the working calibration range, two stock solutions of compound (25) were prepared at concentrations of 554 ppm (pg / ml) and 1184 ppm (pg / ml). A 10:1 serial dilution was applied to each stock solution until concentrations of 5.54 parts per billion (ppb) and 1.18 ppb were achieved, respectively. Standards with concentrations between 5.54 ppm and 1.18 ppb (a total of eight standards) were injected using Method 3, and a linear calibration with offset (ignoring the origin) was used to evaluate the calibration range. The lower limit of the working range was estimated by the lowest concentration standard with a relative percent residual within + / - 20%. For molecule (25), the LOD was determined to be 55.4 parts per billion with a residual of -5.75%.

[0789] Example 2

[0790] Reaction of 4-aminodiphenylamine with isopropylidene acetone

[0791] A 50-mL reactor equipped with magnetic stirrer, temperature control, addition funnel, nitrogen inlet, and reflux condenser with receiver was charged with 5.54 g of 4-aminodiphenylamine (30 mmol; 99.2% purity) and 0.5 mL of concentrated hydrochloric acid (6 mmol, 37%, d = 1.18) catalyst. Heated to 100 °C while stirring under nitrogen. 23 mL of isopropylidene acetone (180 mmol, 90% technical grade, Sigma, d = 0.858) was fed over 2 hours at 100 °C while stirring under nitrogen. Maintained for another 2.5 hours at the same conditions, monitored the reaction completion by HPLC analysis (Method 1). Neutralized with 4 mL of 15% aqueous sodium carbonate solution. Cooled to room temperature. The contents of the reactor were transferred into a separatory funnel with 50 mL of chloroform and 20 mL of water in 2 batches. The layers were separated and the aqueous layer was discarded. The chloroform and some portion of isopropylidene acetone were removed by rotary evaporation. Recovered 9.7 g of 59.1% of compound (10), about 10% of total unreacted starting materials (9% of isopropylidene acetone and 1% of 4-aminodiphenylamine), and other unexpected molecules (i.e. byproducts) as measured by area percent HPLC. See Example 1, Table 1, and Table 5 for detailed information of HPLC analysis. It has not been determined whether the HPLC peak at 7.3 minutes is compound (11A), compound (11B), compound (20A), or compound (20B).

[0792] Table 5

[0793]

[0794] Example 3

[0795] Reaction of 4-aminodiphenylamine with acetone and isopropylidene acetone

[0796] To a stirred solution of 4-aminodiphenylamine (1.50 g, 8.14 mmol) in 3:2 v:v acetone:isopropylidene acetone (5 mL) at room temperature was added zinc triflate (0.296 g, 0.814 mmol). The stirred mixture was heated to 80 °C and maintained for 22 hours. The mixture was then allowed to stand at room temperature and cool for 10 minutes. Decanting was then performed by pouring the solution into a clean flask. The remaining precipitate was rinsed in two batches with 20 mL of acetone and combined with the solution in the flask. The resulting solution was then evaporated under reduced pressure to give 3.08 g of material containing compound (10) and other unexpected molecules (i.e. byproducts, including compounds (2), (21), (23), (25), and (37)). Figure 2-5 and 23.

[0797] Example 4

[0798] 4-aminodiphenylamine with acetone

[0799] To a solution of 4-aminodiphenylamine (750.0 g, 2.7 mol) in acetone (1800 mL) was added zinc triflate (148 g, 0.27 mol) under nitrogen atmosphere at room temperature. The resulting mixture was heated to 60-65 °C and maintained for 20 h. After completion of the reaction, it was allowed to cool to room temperature and filtered through a bed of celite. The celite bed was washed with ethyl acetate, the filtrate was collected and evaporated under reduced pressure. This procedure was repeated 4 times and the crude material was combined. The combined crude material was purified using silica gel (100-200 mesh) by column chromatography eluting with 5-10% ethyl acetate in hexane to get 1534.0 g of purified compound (10) as a light yellow solid. Analysis of the final material by method 1 showed 98.5% of compound (10) and other unexpected molecules (i.e. byproducts). Figure 6 and 7 .

[0800] Example 5

[0801] 2-aminodiphenylamine with acetone

[0802] A 50-mL reactor was charged with 5.53 g of 2-aminodiphenylamine (30 mmol, Sigma) and 0.25 mL of concentrated hydrochloric acid catalyst (3 mmol, 37%, d = 1.18), equipped with a magnetic stirrer, temperature control, an addition funnel, a nitrogen inlet, and a reflux condenser with a receiver. Heated to 95 °C while stirring under nitrogen. Feeding 13.5 mL of acetone (180 mmol, ACS grade, d = 0.784) at 95 °C over 1.5 h while stirring under nitrogen. Held for another 1.5 h under the same conditions. Neutralized with 2 mL of 15% aqueous sodium carbonate solution. Cooled to room temperature. The contents of the reactor were transferred in 2 batches to a separatory funnel with 50 mL of toluene and 20 mL of water. The layers were separated and the water was discarded. The toluene was removed by rotary evaporation. 5.6 g of material was recovered containing 4.5% of 8- anilino-2,2,4-trimethyl-1,2-dihydroquinoline (compound (2)), 65.6% of unreacted 2- aminodiphenylamine (“2-ADPA”) starting material, and other molecules (i.e. byproducts) as measured by area percent HPLC. See Example 1 and Table 6 for detailed information of HPLC analysis.

[0803] Table 6

[0804]

[0805] Example 6

[0806] Reaction of 2-aminodiphenylamine with isopropylidene acetone

[0807] A 50-mL reactor was charged with 4.28 g of 2-aminodiphenylamine (23.2 mmol, Sigma) and 0.2 mL of concentrated hydrochloric acid (2.4 mmol, 37%, δ = 1.18) catalyst, the reactor was equipped with a magnetic stirrer, temperature control, an addition funnel, a nitrogen inlet, and a reflux condenser with a receiver. Heated to 95 °C while stirring under nitrogen. 11 mL of isopropylidene acetone (91.4 mmol, 95%, TCI, δ = 0.858) was fed over 1 hour at 95 °C while stirring under nitrogen. Held for an additional 1.5 hours under the same conditions. Neutralized with 1.5 mL of 15% aqueous sodium carbonate solution. Cooled to room temperature. Analysis of the crude reaction mass showed 4.6% of compound (2), 65.1% of total unreacted starting materials (42.3% isopropylidene acetone and 22.8% 2-ADPA), and other byproducts as measured by area percent HPLC. See Example 1 and Table 7 for detailed information on HPLC analysis. The HPLC peak at 8.4 minutes has not been identified as compound (11A), compound (11B), compound (20A), or compound (20B).

[0808] Table 7

[0809]

[0810] Example 7

[0811] Synthesis of compound (4) (2,2,4-trimethyl-N-phenylquinolin-6(2H)-imine)

[0812]

[0813] A 250-mL round-bottom flask, equipped with a stir bar, was charged with 2,2,4-trimethyl-N-phenyl-1,2-dihydroquinolin-6-amine (5.5 g; 20.8 mmol) and then blanketed with N2. Acetonitrile (60 mL) was added and the mixture was stirred (the substrate dissolved within a few minutes). A 10-15% aqueous solution of NaOCI (16 mL; 25.9-38.9 mmol hypochlorite anion) was added in portions over 6-7 minutes. The dense liquid separated immediately. The 2-phase system was stirred without external cooling or heating. A slow and mild exotherm occurred, peaking at about 25 minutes. After 30 minutes of reaction, a TLC on silica gel using 20% AcOEt in hexanes as eluent showed complete consumption of the substrate (Rf = 0.45) and the formation of 2 new spots (Rf = 0.2 and 0.4). After about 50 minutes of reaction, a 1.69 mol / L aqueous solution of Na2SO3 (15 mL; 25.35 mmol sulfite anion) was added to quench the excess hypochlorite anion (an exotherm was observed). The 2-phase system was diluted with AcOEt (60 mL) in a separatory funnel. The aqueous phase was discarded. The organic phase was washed with deionized water (60 mL), with a diluted aqueous solution of NaCI (60 mL), with a saturated aqueous solution of NaCI (60 mL), dried over anhydrous MgSO4, filtered, and then stripped of volatiles under reduced pressure (rotary evaporator; water bath = 50 °C). Further drying on the rotary evaporator (50 °C; approximately 10 mbar) until the weight was constant resulted in a dark, viscous liquid (4.7 g; 86% yield relative to 2,2,4-trimethyl-N-phenyl-1,2-dihydroquinolin-6-amine). The structure was verified by NMR spectra, and LC-MS m / z [M+1] = 263. The purity of compound (4) was 99.03% (combined area of 2 stereoisomers) as measured by LC-UV 260 nm. + Figure 8 Figure 9 Proton NMR spectra (DMSO-d6) and HPLC chromatograms are depicted in Figures

[0814] Example 8

[0815] Synthesis of compound (2) (2,2,4-trimethyl-N-phenyl-1,2-dihydroquinolin-8-amine) and compound (21) (11,11 -dimethyl-10,11 -dihydro-5H-dibenzo[b,e][1,4]diazepine)

[0816]

[0817] ​​A 100-mL round bottom flask, equipped with a stir bar and reflux condenser, was charged with compound (32) (10.48 g; 56.9 mmol) and acetone (17.0 mL; 232 mmol). The mixture was stirred under N2protection (2-ADPA readily dissolved). Zinc triflate (2.15 g; 5.91 mmol) was added in one portion and the reaction mixture was gradually heated with an oil bath (temperature set = 70 degrees Celsius). Once temperature was reached, it was maintained for 24 hours. After cooling to room temperature (overnight), the viscous residue was diluted with a mixture of toluene (2 mL) and acetone (3 mL). The resulting free-flowing dark liquid (containing trace amounts of insoluble material) was charged into a 41 mm internal diameter column prepared with silica gel 60 and 10% AcOEt in hexanes. The height of the wet silica gel in the column was 25-26 cm. The flask and column walls were rinsed with toluene (1 mL). The column was eluted with 10% AcOEt in hexanes. Each fraction coming off was analyzed by silica gel TLC. Fraction 1 containing material with an Rf of 0.5 (10% AcOEt in hexanes) was collected. The column was eluted with 30% AcOEt in hexanes. Fraction 2 containing material with an Rf of 0.2 (10% AcOEt in hexanes) was collected. Each fraction was independently stripped of volatiles under reduced pressure (rotary evaporator; water bath = 55 degrees Celsius). Further drying on the rotary evaporator (60 degrees Celsius; 5-15 mbar) until the weight was constant resulted in two products.

[0818] Fraction 1 : Compound (2); isolated yield = 0.37 g; light brown oil that solidified upon standing overnight at room temperature. Structure was verified by NMR spectra and LC-MS m / z [M+1] = 265. Purity as measured by LC-UV 260 nm was 95.2 area %. + = 265. Purity as measured by LC-UV 260 nm was 95.2 area %. Figure 10 and Figure 11 Carbon 13 APT NMR spectra (DMSO-d6) and HPLC chromatograms are depicted in Figures 1 and 2, respectively.

[0819] Fraction 2: Separation yield = 9.2 g; light orange solid. The impure material containing approximately 9% residual 2-ADPA (LC-UV 260 nm) was dissolved in AcOEt (14 mL) using a warm water bath. Hexane (25 mL) was added to the resulting solution under stirring and N2 protection. The mixture was stirred until a solid was separated. An AcOEt-hexane mixture (7 mL and 11 mL, respectively) was added to loosen the solid. The solid was collected by vacuum filtration through a 0.2 μm disposable polyethylene frit and washed with an AcOEt-hexane mixture (4 mL and 7 mL, respectively). The moist beige solid was dried under vacuum at 50°C for several hours, then overnight at room temperature. Yield = 2.5 g, as an almost white solid. The structure was verified by NMR spectroscopy, and LC-MS m / z [M+1] was obtained. + =225. The purity of compound (21), as measured by LC-UV 260nm, is 98.9% (area%). Figure 12 and Figure 13 The carbon-13 APT NMR spectrum (DMSO-d6) and HPLC chromatograms are depicted respectively.

[0820] Example 9

[0821] Synthesis of compounds (23) (1,2,2,4-tetramethyl-N-phenyl-1,2-dihydroquinoline-6-amine) and (24) (N,1,2,2,4-pentamethyl-N-phenyl-1,2-dihydroquinoline-6-amine)

[0822]

[0823] A 250-mL round bottom flask, equipped with a stir bar, was charged with compound (10) (5.0 g; 18.9 mmol). The flask was placed under N2protection and dry DMF (27 mL) was added. Stirring was initiated. Once compound (10) was completely dissolved, anhydrous potassium carbonate (3.317 g; 24.0 mmol) was added. The flask was cooled with a cold tap water bath. Iodomethane (1.5 mL; 24.0 mmol) was added over 1-2 minutes. No significant exotherm occurred. The cooling bath was removed. The reaction mixture was stirred for 21.5 hours without external cooling or heating. Deionized water (27 mL) was added and the mixture was stirred for 30 minutes. AcOEt (100 mL) and deionized water (20 mL) were added and the mixture was stirred until the sticky material dissolved. The resulting 2-phase system was transferred to a separatory funnel and the organic layer was collected. The aqueous layer was extracted with AcOEt (70 mL). The combined organic layers were washed with 1 mol / L aqueous NaOH (3 x 50 mL) and aqueous NaCl, dried over MgSO4, filtered, and stripped of volatiles under reduced pressure (rotary evaporator; water bath = 50 degrees Celsius). Further drying on the rotary evaporator (60 degrees Celsius; <10 mbar; 1 hour) gave the crude material (brown oil; 4.1 g). The crude material was dissolved in 5% AcOEt in hexanes (7 mL). The resulting solution was charged into a 41 mm internal diameter column prepared with silica gel 60 and 5% AcOEt in hexanes. The height of the wet silica gel in the column was 25-26 cm. The column was used to elute with 5% AcOEt in hexanes. Each fraction that came off was analyzed by silica gel TLC. Fraction 1, containing material with an Rf of 0.4 (5% AcOEt in hexanes), was collected. The column was used to elute with 20% AcOEt in hexanes. Fraction 2, containing material with an Rf of 0.15 (5% AcOEt in hexanes), was collected. The volatiles were stripped from each fraction independently under reduced pressure (rotary evaporator; water bath = 50 degrees Celsius). Further drying on the rotary evaporator (60 degrees Celsius; 9-10 mbar) until the weight was constant gave the final product.

[0824] Fraction 1 : Compound (24); isolated yield = 0.8 g; light yellow oil. Structure was verified by NMR spectra, and LC-MS m / z [M+1] + = 293. Purity as measured by LC-UV 260 nm was 99.0 area %. Figure 14 and Figure 15 Carbon 13 APT NMR spectra (DMSO-d6) and HPLC chromatograms are depicted in Figures

[0825] Fraction 2: Compound (23); Isolated yield = 3.2 g; Light yellow oil. Structure verified by NMR spectra and LC-MS m / z [M+1] = 279. Purity 95.5 area% as measured by LC-UV 260 nm. + = 279. Purity 95.5 area% as measured by LC-UV 260 nm. Figure 16 and Figure 17 Carbon 13 APT NMR spectra (DMSO-d6) and HPLC chromatogram are depicted in Figures

[0826] Example 10

[0827] Synthesis of compound (7) (2,2-dimethyl-1-phenyl-2,3-dihydro-1H- benzo[d]imidazole)

[0828]

[0829] A 2-DR vial, equipped with a stir bar, was charged with compound (32) (1.632 g; 8.86 mmol), magnesium bromide hexahydrate (270 mg; 0.924 mmol) and acetone (3 mL; 40.9 mmol). The vial was purged with N2for a few seconds, capped and then heated to 70 degrees Celsius (heating block) for 17 hours. After cooling to room temperature, the post-reaction mixture was directly charged into a 1 inch internal diameter column prepared with neutral alumina (grade I) and 10% AcOEt in hexane. The height of the alumina in the column was 11-12 cm. The column was used for elution with 10% AcOEt in hexane. Each fraction coming out was analyzed by neutral alumina TLC (20% AcOEt in hexane). Fractions containing the spot at Rf= 0.6 were collected, combined and stripped of volatiles under reduced pressure (rotary evaporator; water bath = 45 degrees Celsius). Further drying on the rotary evaporator (45 degrees Celsius) until constant weight was obtained to give a light brown oil (0.2 g) which solidified to a beige solid after standing at room temperature overnight. Structure verified by NMR spectra and LC-MS m / z [M+1] = 225. Purity of compound (7) 84.2 area% as measured by LC-UV 260 nm (chromatogram also shows 12.5 area% of compound (32)). + = 279. Purity 95.5 area% as measured by LC-UV 260 nm. Figure 18 and Figure 19 Carbon 13 APT NMR spectra (CD2Cl2) and HPLC chromatogram are depicted in Figures

[0830] Example 11

[0831] Synthesis of compound (25) (N,2,2,4-tetramethyl-N-phenyl-1,2-dihydroquinolin-6- amine)

[0832]

[0833] A 250-mL round bottom flask, equipped with a stir bar and a reflux condenser, was charged with the substrate 6-bromo-2,2,4-trimethyl-1,2-dihydroquinoline (1.415 g; 5.61 mmol), anhydrous grade toluene (20.5 mL) and N-methylaniline (0.63 mL; 5.81 mmol). The mixture was stirred under N2 coverage. Once the substrate was completely dissolved (few minutes), dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine (0.1159 g; 0.243 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.1238 g; 0.135 mmol) and sodium tert-butoxide (0.6087 g; 6.33 mmol) were sequentially added to the flask. N2 was bubbled through the mixture for about one minute, then the reaction mixture was heated (oil bath temperature set to 105 degrees Celsius) under N2 coverage for 3.5 hours. After cooling to room temperature (overnight), the post-reaction mixture was filtered under suction over Celite S. The filter cake was rinsed with toluene. The combined filtrates were stripped of volatiles under reduced pressure (rotary evaporator; water bath = 70 degrees Celsius). The obtained brown oil was diluted with hexane (4 mL) and the obtained solution was charged into a 1-inch internal diameter column prepared with silica gel 60 and 5% AcOEt in hexane. The height of the wet silica gel in the column was approximately 18 cm. The column was used for elution with 5% AcOEt in hexane. Each fraction coming out of the column was analyzed by silica gel TLC (5% AcOEt in hexane). The fractions containing the spot at Rf = 0.2 were combined and stripped of volatiles under reduced pressure (rotary evaporator; water bath = 50 degrees Celsius). Drying under vacuum at 50 degrees Celsius for few hours, then at room temperature overnight, afforded 1.212 g of very viscous light brown oil. The structure was verified by NMR spectra and LC-MS m / z [M+1] = 279. The purity of compound (25) was 98.6 area% as measured by LC-UV 260 nm. + Figure 20 , Figure 21 and Figure 22 depict the proton and carbon 13 APT NMR spectra (DMSO-d6) and HPLC chromatogram, respectively.

[0834] Example 12

[0835] Synthesis of compound (8) (1-phenyl-1H-benzo[d]imidazole)

[0836]

[0837] ​To a stirred solution of formic acid (425 mL) was added 2-amino-diphenylamine (85.0 g, 0.46 mol) at room temperature. The reaction was heated to 100 °C and maintained for 16 h. After completion of the reaction (monitored by TLC), it was cooled to room temperature and the reaction mass was dissolved in DCM (500 mL) and washed with water (2 x 200 mL) followed by saturated NaHC03solution. The organic layer was separated and evaporated under reduced pressure at 45 °C to get 75.0 g of crude compound (8).

[0838] Purification: The obtained crude compound was purified by column chromatography using silica gel (60-120 mesh) as stationary phase eluting with 0-15% ethyl acetate in hexane, pure fractions were collected and evaporated under reduced pressure to get the desired compound (8) 55.0 g as brownish semi solid.

[0839] 1 H NMR (400 MHz, DMSO-d6): d 8.57 (s, 1H), 7.80 (dd, J = 4.8 Hz, 1H), 7.79-760 (m, 1H), 7.51 (t, J = 7.2 Hz, 1H), 7.49-7.29 (m, 1H). 13 C NMR (100 MHz, DMSO-d6): d 147.39, 143.71, 136.46, 133.56, 130.50, 128.13, 124.08, 123.91, 122.92, 120.48, 111.08, 40.63, 40.42, 40.00, 39.80, 39.59, 39.38.

[0840] Example 13

[0841] Synthesis of compound (34) (N-(2-(phenylamino)phenyl)formamide)

[0842]

[0843] To a stirred solution of 2-amino-diphenylamine (2.5 g, 13.58 mmol) in THF (25 mL, 10 vol) was added N-formyl saccharin (2.8 g, 13.58 mmol) at RT and stirred for 15-20 min. After completion of the reaction (monitored by TLC), it was quenched with saturated NaHC03solution (12 mL) and extracted with DCM (30 mL). The organic layer was separated, dried over sodium sulfate, filtered and evaporated under vacuum to get 3.4 g of crude compound (34). The crude obtained was purified by silica gel (100-200 mesh) column chromatography eluting in hexane with 15-20% ethyl acetate and pure fractions were collected and solvent was evaporated under reduced pressure to get pure compound (34) as off-white solid (by 1 H NMR observed as rotamers). Yield 1.5 g.

[0844] 1 H NMR (400 MHz, DMSO-d6 at 90 °C): δ 9.21 (s, 1H), 8.32 (s, 1H), 7.73 (br s, 1H), 7.22-7.15 (m, 3H), 7.10-7.06 (m, 2H), 7.01-6.97 (m, 1H), 6.84-6.82 (m, 2H), 6.80-6.76 (m, 1H). 13 C NMR (100 MHz, DMSO-d6): δ 163.87, 160.73, 145.31, 144.41, 135.74, 134.54, 130.88, 129.60, 129.53, 126.25, 125.45, 123.55, 123.22, 122.63, 122.20, 120.52, 119.96, 119.50, 116.79, 116.21.

[0845] Example 14

[0846] Synthesis of compound (37) (2-methyl-l-phenyl-lH-benzo[d]imidazole)

[0847]

[0848] To a stirred solution of 2-amino-diphenylamine (100.0 g, 0.54 mol) in acetic acid (500 mL) was added at room temperature. Heated to 90 °C and maintained for 16 h. After completion of the reaction (monitored by TLC), cooled to room temperature and the reaction mass was dissolved in DCM (500 mL), washed with water (2 x 200 mL) followed by saturated NaHC03solution. The organic layer was separated and evaporated under reduced pressure at 45 °C to get 110.0 g of crude compound of compound (37).

[0849] Purification: The obtained crude compound was purified by column chromatography using silica gel (60-120 mesh) as the stationary phase for elution with 0-15% ethyl acetate in hexane, pure fractions were collected and evaporated under reduced pressure to get the desired compound (60.0 g) as a light pink solid.

[0850] 1 H NMR (400 MHz, DMSO-d6): δ 7.66 (t, J = 7.2 Hz, 3H), 7.64-7.53 (m, 3H), 7.24-7.15 (m, 2H), 7.10 (d, J = 7.2 Hz, 1H), 2.43 (s, 3H). 13 C NMR (100 MHz, DMSO-d6): δ 151.74, 142.90, 136.07, 130.43, 129.12, 127.34, 122.75, 122.39, 118.97, 110.21, 40.67, 40.63, 40.46, 40.42, 40.25, 40.21, 40.00, 39.79, 39.58, 14.57.

[0851] Example 15

[0852] Synthesis of compound (38) (N1-methyl-N1-phenylbenzene-1,4-diamine)

[0853]

[0854] To a stirred and degassed toluene solution (2000 mL) was added Pd2dba3 (23.2 g, 0.025 mol), X-Phos (6 g, 0.012 mol) at RT and degassed for 15 min, then the reaction contents were heated to 60 °C. Then p-chloronitrobenzene (100.0 g, 0.63 mol) and N-methylaniline (75 g, 0.69 mol) were added followed by NaOtBu (91.5 g, 0.95 mol). The resulting reaction mixture was heated to 90 °C and stirred for 16 h. The reaction was complete, monitored by TLC, cooled to RT and filtered through a pad of celite and washed with ethyl acetate (300 mL). The combined filtrate was washed with water, dried over Na2SO4 and evaporated under reduced pressure to get crude intermediate 1 (75.0 g).

[0855] Purification: The above obtained crude product was purified by column chromatography using silica gel (100-200 mesh) as the stationary phase for elution with 5-10% ethyl acetate in hexane. Pure fractions were collected and the solvent was evaporated under vacuum to get the desired intermediate 1 (60.0 g) as a brown solid.

[0856] 1 H NMR (400 MHz, DMSO-d6): δ 7.54 (s, 1H), 7.10 (td, J = 8.4, 1.6 Hz, 2H), 6.82 (dd, J = 8.8, 1.2 Hz, 2H), 6.63-6.56 (m, 3H), 6.49 (dd, J = 8.0, 2.0 Hz, 1H), 4.38 (s, 2H), 3.72 (s, 3H).

[0857] Step 2:

[0858] To a stirred solution of intermediate 1 (60 g, 0.26 mol) in methanol (300 mL) was added Raney-Ni (15 g, 25% w / w) at RT. Hydrogen gas pressure (10 kg) was then applied and maintained for 16 h. After completion of the reaction (monitored by TLC), the reaction mixture was filtered through a pad of celite, washed with methanol (150 mL), and the solvent was evaporated to get 55.0 g of compound 38 as a crude product.

[0859] Purification: The crude product obtained above was purified by column chromatography using silica gel (100-200 mesh) as stationary phase eluting with 15% ethyl acetate in hexane. The pure fractions were collected and the solvent was evaporated under vacuum to get the desired 44.0 g of compound (38) as a brown solid.

[0860] 1 H NMR (400 MHz, DMSO-d6): δ 7.54 (s, 1H), 7.10 (td, J = 8.4, 1.6 Hz, 2H), 6.82 (dd, J = 8.8, 1.2 Hz, 2H), 6.63-6.56 (m, 3H), 6.49 (dd, J = 8.0, 2.0 Hz, 1H), 4.38 (s, 2H), 3.72 (s, 3H). 13 C NMR (100 MHz, DMSO-d6): δ 150.49, 146.71, 137.65, 129.12, 127.52, 117.02, 115.27, 114.06.

[0861] Example 16

[0862] Synthesis of compound (39) (N1-methyl-N4-phenylbenzene-1,4-diamine)

[0863]

[0864] To a stirred and degassed toluene solution (1000 mL) was added Pd2dba3(18.6 g, 0.02 mol), X-Phos (4.8 g, 0.01 mol) at RT and degassed for 15 min, then the reaction mixture was heated to 60 °C and added 4-bromo-N-methylaniline (95.0 g, 0.30 mol), aniline (53 mL, 0.6 mol) followed by NaOtBu (73 g, 0.76 mol). The resulting reaction mixture was heated to 90 °C and stirred for 16 h. The reaction was complete, monitored by TLC, cooled to RT and filtered through a pad of celite and washed with ethyl acetate (250 mL). The combined filtrate was washed with water, dried over Na2S04and the solvent was evaporated under reduced pressure to get 125.0 g of crude compound (39).

[0865] Purification: The above obtained crude product was purified by column chromatography using silica gel (100-200 mesh) as stationary phase eluting with 5-10% ethyl acetate in hexane. The pure fractions were collected and evaporated under vacuum to get 42.0 g of compound (39) as light brown solid.

[0866] 1 H NMR (400 MHz, DMSO-d6): d 7.48 (s, 1H), 7.09 (t, J = 8.4 Hz, 2H), 6.90 (d, J = 8.4 Hz, 2H), 6.77 (d, J = 7.6 Hz, 2H), 6.59 (t, J = 7.2 Hz, 1H), 6.59 (d, J = 8.4 Hz, 2H), 5.38 (q, J = 10.0 Hz, 1H), 2.65 (d, J = 5.2 Hz, 3H). 13 C NMR (100 MHz, DMSO-d6): d 147.17, 146.07, 131.91, 129.43, 123.09, 117.47, 114.08, 112.84, 30.72.

[0867] Example 17

[0868] Synthesis of compound (40) (3-methoxy-N1-phenylbenzene-1,4-diamine)

[0869]

[0870] A mixture of compound (10) (50.0 g, 0.189 mol) and sodium hydroxide (200.0 g, 400% w / w) was heated at 140-150 °C and stirred at the same temperature for 16 h. After 16 h, it was cooled to RT, quenched with water and extracted with DCM (500 mL). The organic layer was separated, dried over sodium sulfate, filtered and evaporated under vacuum to get 60.0 g of crude compound (49).

[0871] 1 H NMR (400 MHz, DMSO-d6): δ 7.54 (s, 1H), 7.10 (td, J = 8.4, 1.6 Hz, 2H), 6.82 (dd, J = 8.8, 1.2 Hz, 2H), 6.63-6.56 (m, 3H), 6.49 (dd, J = 8.0, 2.0 Hz, 1H), 4.38 (s, 2H), 3.72 (s, 3H). 13 C NMR (100 MHz, DMSO-d6): δ 147.31, 146.83, 132.95, 132.91, 129.44, 117.69, 114.71, 114.41, 113.80, 105.55, 55.66.

[0872] Example 18

[0873] Synthesis of compound (49) (2,4-dimethyl-N-phenylquinolin-6-amine)

[0874]

[0875] A mixture of compound (10) (50.0 g, 0.189 mol) and sodium hydroxide (200.0 g, 400% w / w) was heated at 140-150 °C and stirred at the same temperature for 16 h. After 16 h, it was cooled to RT, quenched with water and extracted with DCM (500 mL). The organic layer was separated, dried over sodium sulfate, filtered and evaporated under vacuum to get 60.0 g of crude compound (49).

[0876] Purification: The above obtained crude product was purified by column chromatography over silica gel (100-200 mesh) eluting with 45-50% ethyl acetate in hexane and collecting pure fractions and solvent was evaporated under reduced pressure to get 6.9 g of compound (49) as light brown solid.

[0877] 1 H NMR (400 MHz, CDC13): δ 7.92 (d, J = 9.2 Hz, 1H), 7.50 (d, J = 2.8 Hz, 1H), 7.42 (dd, J = 9.2, 2.8 Hz, 1H), 7.34-7.29 (m, 2H), 7.17 (d, J = 7.2 Hz, 2H), 7.07 (s, 1H), 6.99 (t, J = 7.2 Hz, 1H), 5.96 (s, 1H), 2.65 (s, 3H), 2.55 (s, 3H). 13 C NMR (100 MHz, CDC13): δ 151.06, 138.85, 138.13, 137.85, 135.86, 125.38, 124.76, 122.88, 118.31, 117.96, 116.73, 113.34, 113.19, 102.71, 20.09, 13.96.

[0878] Example 19

[0879] Oxidation Induction Time (OIT) Performance

[0880] The oxidation induction time (OIT) of representative compounds of the present disclosure were evaluated. OIT was measured according to a procedure performed in a differential scanning calorimeter (DSC; TA Instruments, Q200). In this procedure, a 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 the onset of degradation, as observed in the onset of the endothermic process in the DSC trace, is measured.

[0881] 0.5 wt% of a compound of the present disclosure or without an anti-degradant (blank) was mixed with polyisoprene and isothermally heated at 150 °C and / or 160 °C in O2. The OIT (in minutes) is shown in Table 8. As these data indicate, the compounds of the present disclosure show antioxidant activity.

[0882] Table 8

[0883] Material OIT at 150°C (min) OIT at 160°C (min) Blank 1.8 1.4 Compound (2) 35.2 10.9 Compound (4) 27.2 12.1 Compound (7) 24.2 11.8 Compound (8) 2.2 1.1 Compound (10) 60.6 26.6 Compound (21) 25.5 12.3 Compound (23) 84.9 36.3 Compound (24) 31.0 16.0 Compound (25) 23.3 11.3 Compound (32) 4.9 2.1 Compound (33) 2.1 1.2 Compound (34) 7.0 3.3 Compound (35) 2.1 1.2 Compound (36) 1.6 1.1 Compound (37) 1.8 1.2 Compound (38) 5.2 2.2 Compound (39) 17.0 7.2 Compound (40) 32.7 11.9 Compound (49) 23.1 12.9

[0884] Having now fully described the methods, compounds, and compositions herein, it will be understood by those of ordinary skill in the art that the methods, compounds, and compositions can be carried out in a wide and equivalent range of conditions, formulations, and other parameters without affecting the scope of the methods, compounds, and compositions provided herein or any embodiments thereof. All patents, patent applications, and publications cited herein are fully incorporated by reference herein in their entirety.

Claims

1. A compound selected from the group consisting of Compound (2), Compound (21), and Compound (25) or a salt or solvate thereof.

2. The compound of claim 1, which is Compound (2).

3. The compound of claim 1, which is Compound (21).

4. The compound of claim 1, which is Compound (25).

5. A composition comprising: (i) Compound (10): or a salt or solvate thereof; and (ii) one or more molecules, or a salt or solvate thereof, wherein the one or more molecules are selected from the group consisting of: or a combination thereof.

6. The composition of claim 5, wherein the composition comprises Compound (1) in a molecular form.

7. The composition of claim 5 or 6, wherein the composition comprises Compound (2) in a molecular form.

8. The composition of any one of claims 5 to 7, wherein the composition comprises Compound (3) in a molecular form.

9. The composition of any one of claims 5 to 8, wherein the composition comprises Compound (4) in a molecular form.

10. The composition of any one of claims 5 to 9, wherein the composition comprises Compound (5) in a molecular form.

11. The composition of any one of claims 5 to 10, wherein the composition comprises Compound (6) in a molecular form.

12. The composition of any one of claims 5 to 11, wherein the composition comprises Compound (7) in a molecular form.

13. The composition of any one of claims 5 to 12, wherein the composition comprises Compound (8) in a molecular form.

14. The composition of any one of claims 5 to 13, wherein the composition comprises Compound (9) in a molecular form.

15. The composition of any one of claims 5 to 14, wherein the composition comprises Compound (11A) in a molecular form.

16. The composition of any one of claims 5 to 15, wherein the composition comprises Compound (11B) in a molecular form.

17. The composition of any one of claims 5 to 16, wherein the composition comprises Compound (12) in a molecular form.

18. The composition of any one of claims 5 to 17, wherein the composition comprises Compound (13) in a molecular form.

19. The composition of any one of claims 5 to 18, wherein the composition comprises Compound (14) in a molecular form.

20. The composition of any one of claims 5 to 19, wherein the composition comprises Compound (15) in a molecular form.

21. The composition of any one of claims 5 to 20, wherein the composition comprises Compound (16) in a molecular form.

22. The composition of any one of claims 5 to 21, wherein the composition comprises Compound (17) in a molecular form. ​ ​ ​ ​ ​ ​ 23. The composition of any one of claims 5-22, wherein the composition comprises compound (18) in molecular form.

24. The composition of any one of claims 5-23, wherein the composition comprises compound (19) in molecular form.

25. The composition of any one of claims 5-24, wherein the composition comprises compound (20A) in molecular form.

26. The composition of any one of claims 5-25, wherein the composition comprises compound (20B) in molecular form.

27. The composition of any one of claims 5-26, wherein the composition comprises compound (21) in molecular form.

28. The composition of any one of claims 5-27, wherein the composition comprises compound (22) in molecular form.

29. The composition of any one of claims 5-28, wherein the composition comprises compound (23) in molecular form.

30. The composition of any one of claims 5-29, wherein the composition comprises compound (24) in molecular form.

31. The composition of any one of claims 5-30, wherein the composition comprises compound (25) in molecular form.

32. The composition of any one of claims 5-31, wherein the composition comprises compound (26) in molecular form.

33. The composition of any one of claims 5-32, wherein the composition comprises compound (27A) in molecular form.

34. The composition of any one of claims 5-33, wherein the composition comprises compound (27B) in molecular form.

35. The composition of any one of claims 5-34, wherein the composition comprises compound (28) in molecular form.

36. The composition of any one of claims 5-35, wherein the composition comprises compound (29) in molecular form.

37. The composition of any one of claims 5-36, wherein the composition comprises compound (30) in molecular form.

38. The composition of any one of claims 5-37, wherein the composition comprises compound (31) in molecular form.

39. The composition of any one of claims 5-38, wherein the composition comprises compound (32) in molecular form.

40. The composition of any one of claims 5-39, wherein the composition comprises compound (33) in molecular form.

41. The composition of any one of claims 5-40, wherein the composition comprises compound (34) in molecular form.

42. The composition of any one of claims 5-41, wherein the composition comprises compound (35) in molecular form.

43. The composition of any one of claims 5-42, wherein the composition comprises compound (36) in molecular form.

44. The composition of any one of claims 5-43, wherein the composition comprises compound (37) in molecular form.

45. The composition of any one of claims 5-44, wherein the composition comprises compound (38) in molecular form.

46. The composition of any one of claims 5-45, wherein the composition comprises compound (39) in molecular form.

47. The composition of any one of claims 5-46, wherein the composition comprises compound (40) in molecular form.

48. The composition of any one of claims 5-47, wherein the composition comprises compound (41) in molecular form.

49. The composition of any one of claims 5-48, wherein the composition comprises compound (42) in molecular form.

50. The composition of any one of claims 5-49, wherein the composition comprises compound (43) in molecular form.

51. The composition of any one of claims 5-50, wherein the composition comprises compound (44) in molecular form.

52. The composition of any one of claims 5-51, wherein the composition comprises compound (45) in molecular form.

53. The composition of any one of claims 5-52, wherein the composition comprises compound (46) in molecular form.

54. The composition of any one of claims 5-53, wherein the composition comprises compound (47) in molecular form.

55. The composition of any one of claims 5-54, wherein the composition comprises compound (48) in molecular form.

56. The composition of any one of claims 5-55, wherein the composition comprises compound (49) in molecular form.

57. The composition of any one of claims 5-56, wherein the composition comprises compound (50) in molecular form.

58. The composition of claim 5, wherein the composition comprises compound (2) and compound (21) in molecular form.

59. The composition of claim 5, wherein the composition comprises compound (2) and compound (25) in molecular form.

60. The composition of claim 5, wherein the composition comprises compound (2) and compound (37) in molecular form.

61. The composition of claim 5, wherein the composition comprises compound (21) and compound (25) in molecular form.

62. The composition of claim 5, wherein the composition comprises compound (21) and compound (37) in molecular form.

63. The composition of claim 5, wherein the composition comprises compound (25) and compound (37) in molecular form.

64. The composition of claim 5, wherein the composition comprises compound (2), compound (21), and compound (25) in molecular form.

65. The composition of claim 5, wherein the composition comprises compound (2), compound (21), and compound (37) in molecular form.

66. The composition of claim 5, wherein the composition comprises compound (2), compound (25), and compound (37) in molecular form.

67. The composition of claim 5, wherein the composition comprises compound (21), compound (25), and compound (37) in molecular form.

68. The composition of claim 5, wherein the composition comprises compound (2), compound (21), compound (25), and compound (37) in molecular form.

69. The composition of any one of claims 5-68, comprising about 50% to about 99% of compound (10) as measured by HPLC and / or GC analysis.

70. The composition of claim 69, comprising about 89% to about 99% of compound (10) as measured by HPLC and / or GC analysis.

71. The composition of any one of claims 5-70, comprising about 0.000001% to about 10% of any one or more molecules as measured by HPLC and / or GC analysis.

72. The composition of claim 71, comprising about 0.0001% to about 5% of any one or more molecules as measured by HPLC and / or GC analysis.

73. The composition of claim 72, comprising about 0.001% to about 3% of any one or more molecules as measured by HPLC and / or GC analysis.

74. The composition of any one of claims 5-70, wherein the weight ratio of any one or more molecules to compound (10) is 0.000001 to 0.

1.

75. A composition comprising the compound of any one of claims 2-4, and (i) one or more elastomers; or (ii) one or more fillers; or (iii) one or more rubber chemicals; or (iv) one or more plasticizers; or (v) one or more second anti-degradants; or (vi) 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 second anti-degradants.

76. A composition comprising the composition of any one of claims 5-74, and (i) one or more elastomers; or (ii) one or more fillers; or (iii) one or more rubber chemicals; or (iv) one or more plasticizers; or (v) one or more second anti-degradants; or (vi) 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 second anti-degradants. ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ 77. A vulcanized elastomeric article comprising the composition of claim 75 or 76.

78. A vehicle comprising the vulcanized elastomeric article of claim 77.

79. A kit comprising the composition of claim 77 or 78 and instructions for using the composition to prepare a vulcanized elastomeric article.

80. A method for preparing the composition of any one of claims 5 to 74, the method comprising reacting a composition comprising 4-aminodiphenylamine with acetone, 2,2-dimethoxypropane, diacetone alcohol, or isopropylidene acetone in the presence of a catalyst.

81. The method of claim 80, wherein the catalyst is a homogeneous catalyst.

82. The method of claim 81, wherein the homogeneous catalyst is a Lewis acid, a Bronsted acid, a base, a halogen, a halogen donor, or a combination thereof.

83. The method of claim 81, wherein the homogeneous catalyst is selected from the group consisting of iodine, pyridinium perbromide, bromine, bismuth(III) trifluoromethanesulfonate, zinc(II) trifluoromethanesulfonate, hydrobromic acid, magnesium(II) bromide, aluminum(III) chloride, p-toluenesulfonic acid monohydrate, N-bromosuccinimide, copper(II) bromide, copper(II) chloride, methanesulfonic acid, benzenesulfonic acid, boron trifluoride diethyl etherate, boron trifluoride dihydrate, hydrochloric acid, copper(II) trifluoromethanesulfonate, iron(III) chloride, magnesium(II) chloride, copper(I) iodide, and zinc(II) chloride, or a salt or solvate thereof.

84. The method of claim 83, wherein the homogeneous catalyst is selected from the group consisting of pyridinium perbromide, magnesium(II) bromide, magnesium(II) bromide hexahydrate, and aluminum(III) chloride.

85. The method of claim 80, wherein the catalyst is a heterogeneous catalyst.

86. The method of claim 85, wherein the heterogeneous catalyst is an acid-treated resin, a solid-supported acid, a composite catalyst, a solid acid, or a base catalyst.

87. The method of claim 86, wherein the acid-treated resin is a polyfluorinated sulfonic acid resin, a strongly acidic sulfonic acid exchange resin (Amberlyst 15), a macroporous strongly acidic ion exchange resin, a strongly acidic ion exchange resin, a solid acidic ion exchange resin (NRW150), a sieved strongly acidic ion exchange resin, or a strongly acidic ion exchange resin (A2 type acid resin).

88. The method of claim 86, wherein the solid supported acid is micro-meso-macro pore zeolite catalyst H-Y-MMM, strong acidity molecular sieve H-MCM-22, organic protic acid supported by graphene oxide, organic protic acid supported by zeolite, small pore size zeolite, heterogeneous acidic silica catalyst, Zn 2+ , Sn 2+ and Cu 2+ exchanged phosphotungstic acid (TPA), tonsil active earth (acid treated bentonite), alumina, titania, zirconia, niobia, silica-alumina, sulfated zirconia, tungstated zirconia, p-toluene sulfonic acid (p-TSA) / ZnCl2or WO3 / activated carbon / SO3H.

89. The method of claim 86, wherein the composite catalyst is a zirconium-doped titanium dioxide composite oxide catalyst, a H2SO4-MoO3-TiO2 solid superacid, or p-toluenesulfonic acid / iodine.

90. The method of claim 86, wherein the solid acid is a heteropoly acid or a metal-organic framework.

91. The method of claim 86, wherein the base catalyst is ZrO2 / MgO.

Images