Decomposition-preventing compound and its use

Abstract

The present disclosure provides a compound represented by formula (I): JPEG2025518619000107.jpg23165 or a salt or solvate thereof [wherein R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , and X are as defined in the specification]. The present disclosure also provides a composition, a vulcanized elastomer article, a lubricant composition, a combustible fuel composition, and a fuel additive composition containing the compound disclosed herein. The present disclosure also provides a process for preparing the composition and the vulcanized elastomer article described herein. The present disclosure also provides a process for retreading a tire using the composition described herein. The present disclosure also provides a kit containing the composition described herein.

Description

Technical Field

[0001] The present disclosure provides compounds that are additives useful for vulcanized rubber articles with anti-degradation (e.g., anti-ozone degradation, anti-oxidation, and / or anti-fatigue) properties, and compositions comprising elastomers, lubricants, fuels, and other compositions that are themselves useful as compositions that require such properties or impart such properties in a composition.

Background Art

[0002] Many materials (e.g., plastics, elastomers, elastomeric products (tires, belts, hoses, bushings, mounts, vibration isolation devices, etc.), lubricants, and petroleum products (working fluids, oils, fuels, and oil / fuel additives for automotive and aircraft applications, etc.)) tend to degrade upon exposure to light, heat, oxygen, ozone, repeated mechanical action, and extended exposure to the like. Thus, compounds and compositions demonstrating anti-degradation effectiveness are well known in the art. For example, U.S. Patent No. 8,987,515 discloses aromatic polyamines useful in inhibiting oxidative decomposition reactions, particularly in lubricant compositions. U.S. Patent Application Publication No. 2014 / 0316163 discloses antioxidant macromolecules with improved solubility, purportedly, in many commercially available oils and lubricants.

[0003] Antioxidants useful in the manufacture of products formed from elastomers, plastics, and the like require a very special combination of qualities that can be difficult to achieve. The antioxidants must clearly have a commercially acceptable effectiveness, but must also be effective over long periods of time, particularly on the exposed surfaces of articles where degradation mainly occurs due to environmental factors (such as light, oxygen, and ozone). Just as the protection of components exposed on the surface is important, the effectiveness in protecting the embedded components of composite materials from the effects of oxidative aging and repeated mechanical action is very important. The antioxidants must achieve these results while not negatively affecting the effectiveness or desired characteristics of other additives in the final article. Furthermore, antioxidants that provide or improve the mechanical fatigue life of an article after it has been used, oxidatively aged, or exposed to ozone are highly regarded because they essentially improve the useful mechanical lifespan of the article. Therefore, elastomeric articles that are subjected to repeated mechanical flexing, extension, or compression during use will benefit greatly from such elucidation.

[0004] Articles formed from general-purpose elastomers (such as natural rubber), especially tires, tend to degrade particularly due to both oxygen and ozone. As discussed in U.S. Patent No. 2,905,654, the effect of oxygen degradation on rubber is different from the effect of ozone degradation. However, both effects can be harmful to the performance, appearance, and lifespan prediction of tires. Fatigue and crack propagation are also particular concerns, especially in the edge regions of steel belts and the sidewalls of tires that are subjected to significant stress and tensile forces while being bent throughout the lifespan of the tire, whether they are partially inflated or inflated. U.S. Patent No. 8,833,417 describes an antioxidant system that presumably increases the resistance to long-term fatigue and crack propagation compared to known antioxidants discussed immediately thereafter. Materials with anti-decomposition effectiveness are well-known in the art for use in tire applications and are commercially available. For example, Ν,Ν'-disubstituted paraphenylenediamine (such as those sold under the trademark Santoflex®) is generally preferred by many tire manufacturers for this purpose. EP3147321A1 discloses a rubber composition, a tire, an amine compound, and an antioxidant, and in particular, a rubber composition said to be suitable for use in the tread rubber or sidewall rubber of a tire.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Patent Document 2

Patent Document 3

Summary of the Invention

Means for Solving the Problems

[0006] The present disclosure provides compounds useful as anti-decomposition agents (such as anti-ozone degradation agents and / or antioxidants) and / or as additives in lubricants or combustible fuels, which are represented by any one of the following formulas I to VI, (VIa), (IVa), or (Va), and are referred to herein collectively as "Compounds of the Disclosure" or individually as "a Compound of the Disclosure".

[0007] The present disclosure provides (i) a Compound of the Disclosure; and (ii) one or more elastomers; or (iii) one or more fillers; or (iv) one or more rubber chemicals; or (v) one or more plasticizers; or (vi) a second antioxidant; or

[0008] (vii) a composition comprising a combination of one or more elastomers, one or more fillers, one or more rubber chemicals, one or more plasticizers, and / or a second antioxidant, which is collectively referred to herein as "the plural compositions of the disclosure" or individually as "one composition of the disclosure", is also provided.

[0009] The disclosure also provides plural compositions of the disclosure comprising one compound of the disclosure and one or more elastomers.

[0010] The disclosure also provides plural compositions of the disclosure comprising one compound of the disclosure and one or more fillers.

[0011] The disclosure also provides plural compositions of the disclosure comprising one compound of the disclosure and one or more rubber chemicals.

[0012] The disclosure also provides plural compositions of the disclosure comprising one compound of the disclosure and one or more plasticizers.

[0013] The disclosure also provides plural compositions of the disclosure comprising one compound of the disclosure and a second antioxidant.

[0014] The disclosure also provides plural compositions of the disclosure comprising one compound of the disclosure and one or more carriers.

[0015] The disclosure also provides a process for preparing a composition comprising one compound of the disclosure and one or more carriers, the process comprising mixing the compound and one or more carriers.

[0016] The present disclosure also provides a vulcanized elastomer article comprising one compound of the present disclosure.

[0017] The present disclosure also provides a vulcanized elastomer article prepared using a composition described herein (e.g., a plurality of compositions of the present disclosure, or a composition comprising one compound of the present disclosure and one or more carriers).

[0018] The present disclosure is a process for preparing a vulcanized elastomer article described herein, (a) forming the composition described herein into a shaped form; (b) vulcanizing the shaped form to provide a vulcanized elastomer article, and the process comprising the foregoing is also provided.

[0019] The present disclosure also provides a lubricant composition comprising a lubricant and one compound of the present disclosure.

[0020] The present disclosure also provides a combustible fuel composition comprising a combustible fuel and one compound of the present disclosure.

[0021] The present disclosure also provides a fuel additive composition comprising a fuel additive and one compound of the present disclosure.

[0022] The present disclosure is a process for retreading a tire, (a) applying the composition described herein to the tire; (b) disposing a precured tread around the tire; (c) disposing a curing envelope around the tire; (d) vulcanizing the tire, and the process comprising the foregoing is also provided.

[0023] The present disclosure also provides a kit comprising a composition described herein and instructions for using the composition in a vulcanizable elastomer composition.

[0024] The present disclosure also provides a kit that includes the compositions described herein and instructions for using the compositions to prepare vulcanized elastomer articles.

[0025] Additional embodiments and advantages of the present disclosure will be set forth in part in the description which follows, and in part will be obvious from the description, or may be learned by practice of the present disclosure. The 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.

[0026] It is to be understood that both the foregoing summary and the following detailed description are exemplary and explanatory only and are not restrictive of the invention as claimed. BRIEF DESCRIPTION OF THE DRAWINGS

[0027]

Figure 1(a)

[0028]

Figure 1(b)

[0029]

Figure 2(a)

[0030]

Figure 2(b)

[0031]

Figure 3(a)

[0032]

Figure 3(b)

[0033]

Figure 4(a)

[0034]

Figure 4(b)

[0035]

Figure 5(a)

[0036]

Figure 5(b)

[0037]

Figure 6(a)

Figure 6(b)

Figure 6(c)

[0038]

Figure 7

[0039]

Figure 8

[0040] In one embodiment, the plurality of compounds of the present disclosure are compounds having the formula (I): **CHEMICAL FORMULA** or a salt or solvate thereof [wherein, R 1 is selected from the group consisting of C1-C 12 alkyl, -CHR 1a R 1b , C3-C6 cycloalkyl, and optionally substituted phenyl; or R 1 and R 4 together with each of the nitrogen and carbon atoms to which they are attached form a saturated or partially saturated 5- or 6-membered heterocycle optionally substituted; R 1a is selected from the group consisting of optionally substituted phenyl, C3-C6 cycloalkyl, and optionally substituted 5- or 6-membered heteroaryl; R 1b is selected from the group consisting of hydrogen and C1-C6 alkyl; R 2 is C1-C 12 alkyl, -CHR 2a R 2b , C3-C6 cycloalkyl, and optionally substituted phenyl; or R 2 and R 8 together with each of the nitrogen and carbon atoms to which they are attached form a saturated or partially saturated 5- or 6-membered heterocycle optionally substituted; R 2ais selected from the group consisting of optionally substituted phenyl, C3-C6 cycloalkyl, and optionally substituted 5- or 6-membered heteroaryl; R 2b is selected from the group consisting of hydrogen and C1-C6 alkyl; X is -CHR 3a -, -NR 3b -, -O-, and -S-; R 3a is hydrogen, C1-C 12 alkyl, C3-C6 cycloalkyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heterocycle, and optionally substituted 5- or 6-membered heteroaryl; R 3b is hydrogen, C1-C 12 alkyl, C3-C6 cycloalkyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heterocycle, and optionally substituted 5- or 6-membered heteroaryl; R 4 R 5 R 6 and R 7 are independently selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy, and C1-C6 alkylthio; or R 1 and R 4 together with the nitrogen and carbon atoms to which they are attached form an optionally substituted 5- or 6-membered saturated or partially saturated heterocycle; R 5 R 6 and R 7 are independently selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy, and C1-C6 alkylthio; R 8 R 9 R 10 and R 11is independently selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy, and C1-C6 alkylthio; or R 2 and R 8 together with each of the nitrogen and carbon atoms to which they are attached form a saturated or partially saturated optionally substituted 5- or 6-membered heterocycle; R 9 , R 10 and R 11 are independently selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy, and C1-C6 alkylthio] is as follows.

[0041] In some embodiments, a plurality of the compounds of the present disclosure are compounds having formula (I) [wherein X is -NR 3b -].

[0042] In some embodiments, a plurality of the compounds of the present disclosure are compounds having formula (I) [wherein X is -O-].

[0043] In some embodiments, a plurality of the compounds of the present disclosure are compounds having formula (I) [wherein X is -O- and R 1 and R 2 are independently selected from the group consisting of -CHR 1a R 1b C3-C6 cycloalkyl, and optionally substituted phenyl].

[0044] In some embodiments, a plurality of the compounds of the present disclosure are compounds having formula (I) [wherein X is -S-].

[0045] In some embodiments, a plurality of the compounds of the present disclosure are compounds having formula (I) [wherein X is -S- and R 1 and R 2 are -CHR 1a R 1b, independently selected from the group consisting of C3-C6 cycloalkyl, and optionally substituted phenyl].

[0046] In some embodiments, a plurality of the compounds of the present disclosure are compounds having formula (I) [wherein X is -CHR 3a -.

[0047] In some embodiments, a plurality of the compounds of the present disclosure are compounds having formula (I) [wherein, if X is -CH2-, then

[0048] (i) R 1 is selected from the group consisting of nonyl, decyl, undecyl, dodecyl, -CHR 1a R 1b , and C3-C5 cycloalkyl; or (ii) R 1 and R 4 together with each of the nitrogen and carbon atoms to which they are attached form a saturated or partially saturated, optionally substituted 5- or 6-membered heterocycle; R 1a is selected from the group consisting of substituted phenyl, C3-C6 cycloalkyl, and optionally substituted 5- or 6-membered heteroaryl; R 1b is selected from the group consisting of hydrogen and C1-C6 alkyl; R 2 is selected from the group consisting of nonyl, decyl, undecyl, dodecyl, -CHR 2a R 2b , and C3-C5 cycloalkyl; or (iii) R 2 and R 8 together with each of the nitrogen and carbon atoms to which they are attached form a saturated or partially saturated, optionally substituted 5- or 6-membered heterocycle; R 2a is selected from the group consisting of substituted phenyl, C3-C6 cycloalkyl, and optionally substituted 5- or 6-membered heteroaryl; R 2b is selected from the group consisting of hydrogen and C1-C6 alkyl] and is.

[0049] In some embodiments, a plurality of compounds of the present disclosure are compounds having formula (I) wherein, if X is -CHCH3-, then at that time,

[0050] (i) R 1 is methyl, ethyl, propyl, butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, -CHR 1a R 1b , selected from the group consisting of C3-C6 cycloalkyl, and optionally substituted phenyl; or (ii) R 1 and R 4 together with each of the nitrogen and carbon atoms to which they are attached form a saturated or partially saturated optionally substituted 5- or 6-membered heterocycle; R 2 is methyl, ethyl, propyl, butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, -CHR 2a R 2b , selected from the group consisting of C3-C6 cycloalkyl, and optionally substituted phenyl; or (iii) R 2 and R 8 together with each of the nitrogen and carbon atoms to which they are attached form a saturated or partially saturated optionally substituted 5- or 6-membered heterocycle] and is.

[0051] In some embodiments, a plurality of compounds of the present disclosure are compounds having formula (I) wherein, if X is -O-, then at that time,

[0052] (i) R 1is selected from the group consisting of methyl, ethyl, propyl, butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, -CHR 1a R 1b , C3-C6 cycloalkyl, and optionally substituted phenyl; or (ii) R 1 and R 4 together with the nitrogen and carbon atoms to which they are attached form a saturated or partially saturated 5- or 6-membered heterocycle optionally substituted; R 2 is selected from the group consisting of methyl, ethyl, propyl, butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, -CHR 2a R 2b , C3-C6 cycloalkyl, and optionally substituted phenyl; or (iii) R 2 and R 8 together with the nitrogen and carbon atoms to which they are attached form a saturated or partially saturated 5- or 6-membered heterocycle optionally substituted] is.

[0053] In some embodiments, a plurality of compounds of the present disclosure are compounds having formula (I) [wherein, if X is -S-, then at that time,

[0054] (i) R 1 is selected from the group consisting of methyl, ethyl, propyl, butyl, tert-butyl, pentyl, hexyl, heptyl, nonyl, decyl, undecyl, dodecyl, -CHR 1a R 1b , C3-C6 cycloalkyl, and optionally substituted phenyl; or (ii) R 1 and R 4 together with the nitrogen and carbon atoms to which they are attached form a saturated or partially saturated 5- or 6-membered heterocycle optionally substituted; R 2 is selected from the group consisting of methyl, ethyl, propyl, butyl, tert-butyl, pentyl, hexyl, heptyl, nonyl, decyl, undecyl, dodecyl, -CHR 2a R 2b , C3-C6 cycloalkyl, and optionally substituted phenyl; or (iii) R 2 and R 8 together with the nitrogen and carbon atoms to which they are attached form a saturated or partially saturated optionally substituted 5- or 6-membered heterocycle] is.

[0055] In some embodiments, a plurality of the compounds of the present disclosure are compounds having formula (I) [wherein, if X is -CH2-, then at that time, R 1 and R 2 are not sec-butyl, -CH(CH3)CH2CH(CH3)CH3, -CH(CH3)CH2CH2CH(CH3)CH3, -CH(CH3)(CH2)5CH3, cyclohexyl, phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-aminophenyl, 4-(isopropylamino)phenyl, 4-((4-methylpentan-2-yl)amino)phenyl, 4-((5-methylhexan-2-yl)amino)phenyl, 4-((octan-2-yl)amino)phenyl, or 4-(cyclohexylamino)phenyl].

[0056] In some embodiments, a plurality of the compounds of the present disclosure are compounds having formula (I) [wherein, if X is -C(CH3)2-, then at that time, R 1 and R 2 are not sec-butyl].

[0057] In some embodiments, a plurality of the compounds of the present disclosure are compounds having formula (I) [wherein, if X is -CH2-, then R 1 and R 2is not -CH2(CH2CH3)CH2CH2CH2CH3, -CH(CH2CH3)CH2CH3, 4-methylcyclohexyl, 4-(tert-butyl)cyclohexyl, 3,5,5-trimethylcyclohexyl, 3,5,5-trimethylcyclohex-2-enyl, 1-phenylethyl, or benzyl.

[0058] In some embodiments, a plurality of compounds of the present disclosure are compounds having formula (I) [wherein, if X is -CH2-, then at that time, R 1 and R 2 are not methyl, ethyl, propyl, isopropyl, or butyl].

[0059] In some embodiments, a plurality of compounds of the present disclosure are compounds having formula (I) [wherein X is -CH2- and R 5 and R 9 are methyl, then at that time, R 1 and R 2 are not sec-butyl].

[0060] In some embodiments, a plurality of compounds of the present disclosure are compounds having formula (I) [wherein X is -CH2- and R 4 and R 8 are methyl, then at that time, R 1 and R 2 are not isopropyl or sec-butyl].

[0061] In some embodiments, a plurality of compounds of the present disclosure are compounds having formula (I) [wherein, if X is -O-, then at that time, R 1 and R 2 are not isopropyl or sec-butyl].

[0062] In some embodiments, a plurality of compounds of the present disclosure are compounds having formula (I) [wherein, if X is -S-, then at that time, R 1 and R 2is not isopropyl, sec-butyl, or -CH(CH3)(CH2)5CH3.

[0063] In another embodiment, a plurality of the compounds of the present disclosure are compounds having formula (II):

Chemical formula

Chemical formula

[0064] In another embodiment, a plurality of the compounds of the present disclosure are compounds having formula (III):

Chemical formula

Chemical formula

[0065] In some embodiments, a plurality of the compounds of the present disclosure are any one of the compounds of formulas (I)-(III) [wherein R 1 and R 2 are independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, and optionally substituted phenyl].

[0066] In some embodiments, a plurality of the compounds of the present disclosure are any one of the compounds of formulas (I)-(III) [wherein R 1 and R 2 are isopropyl].

[0067] In some embodiments, a plurality of the compounds of the present disclosure are any one of the compounds of formulas (I)-(III) [wherein R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are selected from the group consisting of hydrogen and methyl].

[0068] In some embodiments, a plurality of the compounds of the present disclosure are any one of the compounds of formulas (I)-(III) [wherein R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are hydrogen].

[0069] In some embodiments, a plurality of the compounds of the present disclosure are any one of the compounds of formulas (I)-(III) [wherein X is -CHR 3a ; R 3a is

Chemical formula

[0070] In some embodiments, a plurality of the compounds of the present disclosure are any one of the compounds of formulas (I)-(III) [wherein X is -CHR 3a ; R 3a is C1-C 12 alkyl].

[0071] In some embodiments, a plurality of the compounds of the present disclosure are any one of the compounds of formulas (I)-(III) [wherein X is -CHR 3a ; R 3a is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, or tert-butyl].

[0072] In some embodiments, a plurality of the compounds of the present disclosure are any one of the compounds of formulas (I)-(III) [wherein X is -CHR 3a ; R 3a is selected from the group consisting of C2-C 12 alkyl, C3-C6 cycloalkyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heterocycle, and optionally substituted 5- or 6-membered heteroaryl].

[0073] In some embodiments, a plurality of the compounds of the present disclosure are any one of the compounds of formulas (I)-(III) [wherein X is -CHR 3a ; R 3ais C3-C6 cycloalkyl.

[0074] In some embodiments, a plurality of the compounds of the present disclosure are any one of the compounds of formulas (I)-(III) [wherein X is -CHR 3a and R 3a is optionally substituted phenyl].[

[0075] In some embodiments, a plurality of the compounds of the present disclosure are any one of the compounds of formulas (I)-(III) [wherein X is -CHR 3a and R 3a is an optionally substituted 5- or 6-membered heterocycle].[

[0076] In some embodiments, a plurality of the compounds of the present disclosure are any one of the compounds of formulas (I)-(III) [wherein X is -CHR 3a and R 3a is an optionally substituted 5- or 6-membered heteroaryl].[

[0077] In some embodiments, a plurality of the compounds of the present disclosure are any one of the compounds of formulas (I)-(III) [wherein X is -CHR 3a and R 3a is

Chemical formula

[0078] In some embodiments, a plurality of the compounds of the present disclosure are any one of the compounds of formulas (I)-(III) [wherein Q is -O-].[

[0079] In another embodiment, a plurality of the compounds of the present disclosure are compounds having formula (IV):

Chemical formula

[0080] In some embodiments, a plurality of the compounds of the present disclosure are compounds of formula (IV) [wherein R 1c 、R 1e 、R 2c 、and R 2e is independently selected from the group consisting of hydrogen and C2-C6 alkyl]. In some embodiments, R 1c 、R 1e 、R 2c 、and R 2e is independently C2-C6 alkyl. In some embodiments, R 1c 、R 1e 、R 2c 、and R 2e is ethyl.

[0081] In another embodiment, a plurality of the compounds of the present disclosure are compounds having formula (IVa): [Chemical formula] or a salt or solvate thereof [wherein, each [Chemical formula] is a single bond or a double bond; R 1f and R 2f are independently selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, -OH, -SH, C1-C8 alkoxy, C1-C8 alkylthio, arylthio, -C(=O)OR, -OC(=O)R, -C(=O)NRR’, -NRC(=O)R’, -NRR’, -SC(=O)R, -SC(=O)SR, -SC(=O)NRR’, -NRC(=O)SR’, -NRC(=S)SR’, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl; R and R’ are independently selected, at each occurrence, from the group consisting of hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl; R 1g 、R 2g 、R 1i 、and R 2i are independently selected from the group consisting of hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl, provided that R 1e and R 1i linking the carbon atoms to which they are attached

Chemical formula

Chemical formula

[0082] In some embodiments, a plurality of the compounds of the present disclosure are compounds of formula (IVa) [wherein, [Chemical formula] is a single bond].

[0083] In some embodiments, a plurality of the compounds of the present disclosure are compounds of formula (IVa) [wherein, [Chemical formula] is a single bond, and R 1c , R 1f , R 2c , and R 2f are methyl].

[0084] In some embodiments, a plurality of the compounds of the present disclosure are compounds of formula (IVa) [wherein, [Chemical formula] is a single bond, and R 1i , R 1g , R 2i , and R 2g are methyl].

[0085] In another embodiment, a plurality of the compounds of the present disclosure are compounds having formula (V): [Chemical formula] or a salt or solvate thereof [wherein, each [Chemical formula] is a single bond or a double bond; R 1c 、R 1d 、R 1e 、R 2c 、R 2d 、and R 2e is independently selected from the group consisting of hydrogen and C1-C6 alkyl; R 5 、R 6 、R 7 、R 9 、R 10 、and R 11 is as defined in relation to formula (I), provided that

Chemical formula

[0086] In another embodiment, a plurality of the compounds of the present disclosure are compounds having formula (Va):

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0087] In some embodiments, a plurality of the compounds of the present disclosure are compounds of formula (Va) [wherein,

Chemical formula

[0088] In another embodiment, a plurality of the compounds of the present disclosure are compounds having formula (VI):

Chemical formula

Chemical formula

Chemical formula

[0089] In another embodiment, a plurality of the compounds of the present disclosure are compounds having formula (VIa):

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0090] In some embodiments, a plurality of the compounds of the present disclosure are compounds of formula (VIa) [wherein,

Chemical formula

[0091] In some embodiments, a plurality of the compounds of the present disclosure are any one compound of formulae (IV)-(VI), (IVa), (Va), or (VIa) [wherein R 5 、R 6 、R 7 、R 9 、R 10 、and R 11 is selected from the group consisting of hydrogen, methyl, C1-C6 alkoxy, and C1-C6 alkylthio].

[0092] In some embodiments, a plurality of the compounds of the present disclosure are any one compound of formulae (IV)-(VI), (IVa), (Va), or (VIa) [wherein R 5 、R 6 、R 7 、R 9 、R 10 、and R 11is hydrogen]

[0093] In some embodiments, a plurality of the compounds of the present disclosure are any one compound of Formulas (IV)-(VI), (IVa), (Va), or (VIa) [wherein R 1c , R 1d , R 1e , R 2c , R 2d , and R 2e is methyl, ethyl, or hydrogen]

[0094] In some embodiments, a plurality of the compounds of the present disclosure are any one compound of Formulas (IV)-(VI), (IVa), (Va), or (VIa) [wherein R 1c , R 1d , R 1e , R 2c , R 2d , and R 2e is methyl]

[0095] In some embodiments, a plurality of the compounds of the present disclosure are any one compound of Formulas (IV)-(VI), (IVa), (Va), or (VIa) [wherein R 3a is hydrogen]

[0096] In some embodiments, a plurality of the compounds of the present disclosure are any one compound of Formulas (IV)-(VI), (IVa), (Va), or (VIa) [wherein R 3a is

Chemical formula

[0097] In some embodiments, a plurality of the compounds of the present disclosure are any one compound of Formulas (IV)-(VI), (IVa), (Va), or (VIa) [wherein R 3a is C1-C 12is alkyl.

[0098] In some embodiments, a plurality of compounds of the present disclosure are any one compound of formulas (IV)-(VI), (IVa), (Va), or (VIa) [wherein R 3a is methyl, ethyl, propyl, isopropyl, butyl, iso-butyl, sec-butyl, or tert-butyl].

[0099] In some embodiments, a plurality of compounds of the present disclosure are any one compound of formulas (IV)-(VI), (IVa), (Va), or (VIa) [wherein R 3a is

Chemical formula

[0100] In some embodiments, a plurality of compounds of the present disclosure are any one compound of formulas (IV)-(VI), (IVa), (Va), or (VIa) [wherein Q is -O-].

[0101] In some embodiments, a plurality of compounds of the present disclosure are any one or more of the compounds in Table 1 or salts or solvates thereof.

Table 1-1

Table 1-2

Table 1-3

Table 1-4

Table 1-5

Table 1-6

Table 1-7

Table 1-8

Table 1-9

Table 1-10

Table 1-11

Table 1-12

Table 1-13

Table 1-14

Table 1-15

Table 1-16

Table 1-17

Table 1-18

Table 1-19

[0102] A plurality of the compounds of the present disclosure can be useful as anti-degradants (e.g., anti-ozone degradation agents and / or antioxidants), as additives in lubricants, and as additives in combustible fuels.

[0103] A plurality of the compounds of the present disclosure can be prepared by reacting a secondary aniline with an aldehyde in the presence of an acid, as shown in Scheme 1. [Chem.]

[0104] A plurality of the compounds of the present disclosure can also be prepared by reacting 4,4'-alkylenedianiline with a methyl ketone in the presence of an acid, as shown in Scheme 2. [Chem.]

[0105] A plurality of the compounds of the present disclosure can also be prepared by reduction of the compounds obtained in the reaction described by Scheme 2, as shown in Scheme 3. The reduction can be carried out using any method known in the art, such as exposure to hydrogen by a carbon-supported palladium (Pd / C) catalyst. [Chem.]

[0106] A plurality of the compounds of the present disclosure, as shown in Scheme 4 [wherein R 14a , R 14b , R 14c , R 14d , R 14e , and R 15f are, for example, hydrogen or C1-C6 alkyl], can also be prepared, for example, by reacting bis(aminophenyl)methane, bis(aminophenyl)ether, or bis(aminophenyl)sulfide with an alkene and an aldehyde or ketone in acetonitrile or another suitable solvent and catalyst (any suitable acid-base or I2, etc.) (i.e., via the Povarov reaction). [Chem.]

[0107] A plurality of the compounds of the present disclosure can also be prepared by oxidizing the compounds obtained in Scheme 4 by methods known in the art. [Chem.]

[0108] Definition As used herein, the term "alkyl", alone or as part of another group, refers to a straight-chain or branched-chain aliphatic hydrocarbon having from 1 to 12 carbon atoms (i.e., C1-C 12 alkyl), or a specified number of carbon atoms (e.g., C1-C3 alkyl (such as methyl, ethyl, propyl, or isopropyl); C1-C4 alkyl (such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or t-butyl); etc.). In one embodiment, the alkyl is a straight-chain alkyl. In another embodiment, the alkyl is a branched-chain alkyl. In one embodiment, the alkyl is C1-C8 alkyl. In another embodiment, the alkyl is C1-C6 alkyl. In another embodiment, the alkyl is C1-C4 alkyl. In another embodiment, the alkyl is C1-C3 alkyl. Non-limiting exemplary C1-C 12 alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, iso-butyl, 3-pentyl, hexyl, heptyl, octyl, nonyl, and decyl.

[0109] As used herein, the term "halo" or "halogen", alone or as part of another group, refers to -Cl, -F, -Br, or -I.

[0110] As used herein, the term "nitro", alone or as part of another group, refers to -NO2.

[0111] As used herein, the term "cyano", alone or as part of another group, refers to -CN.

[0112] The term "hydroxy", when used herein, either by itself or as part of another group, refers to -OH.

[0113] The term "amino", when used by itself or as part of another group, has the formula -NR 12 R 13 radical [wherein R 12 and R 13 are each independently hydrogen or alkyl or aryl].

[0114] In one embodiment, amino is -NH2.

[0115] In another embodiment, amino is "alkylamino" (i.e., an amino group where R 12 is C 1-6 alkyl and R 13 is hydrogen). In one embodiment, R 12 is C1-C4 alkyl. Non-limiting exemplary alkylamino groups include -N(H)CH3 and -N(H)CH2CH3.

[0116] In another embodiment, amino is "dialkylamino" (i.e., an amino group where R 12 and R 13 are each independently C 1-6 alkyl). In one embodiment, R 12 and R 13 are each independently C1-C4 alkyl. Non-limiting exemplary dialkylamino groups include -N(CH3)2 and -N(CH3)CH2CH(CH3)2.

[0117] In another embodiment, amino is "arylamino" (i.e., an amino group where R 12 is aryl and R 13 is hydrogen). In one embodiment, R 12 is optionally substituted phenyl. In another embodiment, R 12is phenyl, 2-methylphenyl, 3-methylphenyl, or 4-methylphenyl.

[0118] In another embodiment, the amino is a "diaryl amino" (i.e., R 12 and R 13 are each independently an aryl amino group where aryl is). In one embodiment, R 12 and R 13 are phenyl.

[0119] The term "aryl", when used herein, either by itself or as part of another group, refers to an aromatic ring system having 6 to 14 carbon atoms (i.e., C6-C 14 aryl). Non-limiting exemplary aryl groups include phenyl group, naphthyl group, phenanthryl group, anthracyl group, indenyl group, azulenyl group, biphenyl group, biphenylenyl group, and fluorenyl group. In one embodiment, the aryl group is phenyl.

[0120] The term "alkylcarbonyl", when used herein, either by itself or as part of another group, refers to a carbonyl group (-C(=O)-) substituted by an alkyl group. In one embodiment, the alkyl is C1-C4 alkyl. A non-limiting exemplary alkylcarbonyl group is -COCH3.

[0121] The term "haloalkyl", as used herein, either by itself or as part of another group, refers to alkyl substituted by one or more fluorine, chlorine, bromine, and / or iodine atoms. In one embodiment, the alkyl is substituted by 1, 2, or 3 fluorine and / or chlorine atoms. In another embodiment, the alkyl is substituted by 1, 2, or 3 fluorine atoms. In another embodiment, the alkyl is C1-C6 alkyl, and the resulting haloalkyl is referred to as "C1-C6 haloalkyl". In another embodiment, the alkyl is C1-C4 alkyl, and the resulting haloalkyl is referred to as "C1-C4 haloalkyl". In another embodiment, the alkyl group is C1 alkyl or C2 alkyl. Non-limiting exemplary haloalkyl groups include fluoromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, 4,4,4-trifluorobutyl, and trichloromethyl groups.

[0122] The term "alkoxy", as used herein, either by itself or as part of another group, refers to alkyl bonded to a terminal oxygen atom. In one embodiment, the alkyl is C1-C6 alkyl, and the resulting alkoxy is referred to as "C1-C6 alkoxy". In another embodiment, the alkyl is a C1-C4 alkyl group, and thus the resulting alkoxy is referred to as "C1-C4 alkoxy". Non-limiting exemplary alkoxy groups include methoxy, ethoxy, and tert-butoxy.

[0123] The term "alkylthio", when used herein, either by itself or as part of another group, refers to an alkyl group bonded to the terminal sulfur atom. In one embodiment, the alkyl is a C1 alkyl, and the resulting alkylthio is referred to as "C1-C6 alkylthio". In one embodiment, the alkyl group is a C1-C4 alkyl group, and the resulting alkylthio is referred to as "C1-C4 alkylthio". Non-limiting exemplary alkylthio groups include -SCH3 and -SCH2CH3.

[0124] The term "cycloalkyl", when used herein, either by itself or as part of another group, refers to a saturated and partially unsaturated (e.g., containing 1 or 2 double bonds) monocyclic, bicyclic, or tricyclic aliphatic hydrocarbon containing 3 to 12 carbon atoms (i.e., C3-C 12 cycloalkyl) or a specified number of carbons (e.g., C3-C6 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl). In one embodiment, the cycloalkyl is bicyclic (i.e., having 2 rings). In another embodiment, the cycloalkyl is monocyclic (i.e., having 1 ring). In another embodiment, the cycloalkyl is C3-C8 cycloalkyl. In another embodiment, the cycloalkyl is C3-C6 cycloalkyl. In another embodiment, the cycloalkyl is C5 cycloalkyl (i.e., cyclopentyl). In another embodiment, the cycloalkyl is C6 cycloalkyl (i.e., cyclohexyl). Non-limiting exemplary C3-C 12 cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, norbornyl, decalin, adamantyl, cyclohexenyl, and spiro[3.3]heptane.

[0125] The term "optionally substituted phenyl", as used herein, either by itself or as part of another group, refers to phenyl that is either unsubstituted or substituted with 1 to 5 substituents, each substituent being independently halo, nitro, cyano, hydroxyl, amino (e.g., -NH2, alkylamino, dialkylamino, arylamino, or diarylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl, or cycloalkyl.

[0126] The term "heterocycle", as used herein, either by itself or as part of another group, refers to a saturated and partially unsaturated (e.g., containing 1 or 2 double bonds) monocyclic, bicyclic, or tricyclic group containing 3 to 18 ring members (i.e., 3- to 18-membered heterocycle) containing 1, 2, 3, or 4 heteroatoms. Each heteroatom is independently oxygen, sulfur, or nitrogen. Each sulfur atom can be independently oxidized to give a sulfoxide (i.e., S(=O)) or a sulfone (i.e., S(=O)2). The term heterocycle includes groups in which one or more -CH2- groups are replaced by one or more -C(=O)- groups, and examples include cyclic ureido groups (such as imidazolidinyl-2-one), cyclic amide groups (such as pyrrolidin-2-one or piperidin-2-one), and cyclic carbamate groups (such as oxazolidinyl-2-one). The term heterocycle also includes groups having a fused optionally substituted aryl group or an optionally substituted heteroaryl group (such as indoline, indolin-2-one, 2,3-dihydro-1H-pyrrolo[2,3-c]pyridine, 2,3,4,5-tetrahydro-1H-benzo[d]azepine, or 1,3,4,5-tetrahydro-2H-benzo[d]azepin-2-one). In some embodiments, the heterocycle is a 6-membered ring containing one nitrogen atom. The heterocycle can be fused to the rest of the molecule to form a bicyclic group (such as 1,2-dihydroquinoline or 1,2,3,4-tetrahydroquinoline).

[0127] The term "heterocycle optionally substituted" as used herein, either by itself or as part of another group, refers to a heterocyclic group that is either unsubstituted or substituted with 1 to 4 substituents that are independently halo, nitro, cyano, hydroxyl, amino (e.g., -NH2, alkylamino, or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl, or cycloalkyl.

[0128] The term "heteroaryl", as used herein, either by itself or as part of another group, refers to a monocyclic aromatic ring system having 5 to 6 ring members containing 1, 2, 3, 4, or 5 heteroatoms (i.e., 5- to 6-membered heteroaryl). Each heteroatom is independently oxygen, sulfur, or nitrogen. In one embodiment, heteroaryl has 3 heteroatoms. In another embodiment, heteroaryl has 2 heteroatoms. In another embodiment, heteroaryl has 1 heteroatom. In another embodiment, heteroaryl has 5 ring atoms (e.g., furyl, a 5-membered heteroaryl having 4 carbon atoms and 1 oxygen atom). In another embodiment, heteroaryl has 6 ring atoms (e.g., pyridyl, a 6-membered heteroaryl having 5 carbon atoms and 1 nitrogen atom). Non-limiting exemplary heteroaryl groups include thienyl, furyl, pyranyl, 2H-pyrrolyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, thiazolyl, isothiazolyl, and isoxazolyl. In one embodiment, heteroaryl is selected from thienyl (e.g., thien-2-yl and thien-3-yl), furyl (e.g., 2-furyl and 3-furyl), pyrrolyl (e.g., 1H-pyrrol-2-yl and 1H-pyrrol-3-yl), imidazolyl (e.g., 2H-imidazol-2-yl and 2H-imidazol-4-yl), pyrazolyl (e.g., 1H-pyrazol-3-yl, 1H-pyrazol-4-yl, and 1H-pyrazol-5-yl), pyridyl (e.g., pyridin-2-yl, pyridin-3-yl, and pyridin-4-yl), pyrimidinyl (e.g., pyrimidin-2-yl, pyrimidin-4-yl, and pyrimidin-5-yl), thiazolyl (e.g., thiazol-2-yl, thiazol-4-yl, and thiazol-5-yl), isothiazolyl (e.g., isothiazol-3-yl, isothiazol-4-yl, and isothiazol-5-yl), oxazolyl (e.g., oxazol-2-yl, oxazol-4-yl, and oxazol-5-yl), and isoxazolyl (e.g., isoxazol-3-yl, isoxazol-4-yl, and isoxazol-5-yl).The term "heteroaryl" includes N-oxides. A non-limiting exemplary N-oxide is pyridyl N-oxide.

[0129] The term "optionally substituted heteroaryl", as used herein, whether by itself or as part of another group, refers to heteroaryl that is either unsubstituted or substituted with 1 to 4 substituents, the substituents being independently halo, nitro, cyano, hydroxyl, amino (e.g., -NH2, alkylamino, or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl, or cycloalkyl.

[0130] As used herein, the term "stereoisomers" is a general term for all isomers of individual molecules that differ only in the orientation of their atoms in space. It includes enantiomers and isomers (diastereomers) of compounds having two or more chiral centers that are not mirror images of each other.

[0131] The term "chiral center" or "asymmetric carbon atom" refers to a carbon atom to which four different groups are attached.

[0132] The terms "enantiomer" and "enantiomeric" refer to optically active molecules that cannot be superimposed on their mirror images, where if one enantiomer rotates the plane of polarization in one direction, the mirror image compound rotates the plane of polarization in the opposite direction.

[0133] The term "racemate" refers to a mixture of equal parts of enantiomers, the mixture being optically inactive.

[0134] The term "absolute configuration" refers to the spatial arrangement of the atoms of a chiral molecular entity (or group) and its stereochemical description (e.g., R, S).

[0135] The stereochemical terms and conventions used in the specification are intended to be consistent with those described in Pure & Appl.Chem 68:2193(1996) unless otherwise indicated.

[0136] The term "enantiomeric excess" or "ee" refers to a measure of how much one enantiomer is present compared to the other. For a mixture of R and S enantiomers, the percent enantiomeric excess is defined as │R - S│*100, where R and S are the respective molar or weight fractions of the enantiomers in the mixture such that R + S = 1. With knowledge of the specific rotation of the chiral substance, the percent enantiomeric excess is defined as ([α] obs / [α] max )*100, where [α] obs is the specific rotation of the enantiomeric mixture and [α] max is the specific rotation of the pure enantiomer. The determination of enantiomeric excess is possible using a variety of analytical techniques including NMR spectroscopy, chiral column chromatography, or optical rotation analysis.

[0137] In thin layer chromatography (TLC), the term R f represents the retention factor. R f is defined as the distance traveled by an individual component divided by the total distance traveled by the eluent. The value is always between 0 and 1.

[0138] Salts and solvates (e.g., hydrates) of the disclosed compounds may also be used in the methods disclosed herein.

[0139] This disclosure encompasses the preparation and use of salts of a plurality of compounds of the present disclosure. The salts of the plurality of compounds of the present disclosure can be prepared during the final isolation and purification of the compounds, or can be separated and prepared by reacting the compounds with an acid having a suitable cation. The salts of the plurality of compounds of the present disclosure can be acid addition salts formed by acceptable acids. Examples of acids that can be used to form the salts include inorganic acids (such as nitric acid, boric acid, hydrochloric acid, hydrobromic acid, sulfuric acid, and phosphoric acid) and organic acids (oxalic acid, maleic acid, succinic acid, and citric acid). Non-limiting examples of salts of the compounds of the present disclosure include hydrochloride, hydrobromide, hydroiodide, sulfate, bisulfate, 2-hydroxyethanesulfonate, phosphate, hydrogen phosphate, acetate, adipate, alginate, aspartate, benzoate, bisulfate, butyrate, camphorate, camphorsulfonate, digluconate, glycerophosphate, hemisulfate, heptanoate, hexanoate, formate, succinate, fumarate, maleate, ascorbate, isethionate, salicylate, methanesulfonate, mesitylenesulfonate, naphthalenesulfonate, nicotinate, 2-naphthalenesulfonate, oxalate, pamoate, pectinate, persulfate, 3-phenylpropionate, picrate, pivalate, propionate, trichloroacetate, trifluoroacetate, phosphate, glutamate, bicarbonate, undecanoate, lactate, citrate, tartrate, gluconate, methanesulfonate, ethanedisulfonate, benzenesulfonate, and p-toluenesulfonate, but are not limited thereto. In addition, available amino groups present in the compounds of the present disclosure can be quaternized with methyl chloride, ethyl chloride, propyl chloride, and butyl chloride, methyl bromide, ethyl bromide, propyl bromide, and butyl bromide, and methyl iodide, ethyl iodide, propyl iodide, and butyl iodide; dimethyl sulfate, diethyl sulfate, dibutyl sulfate, and diamyl sulfate; decyl chloride, lauryl chloride, myristyl chloride, and stearyl chloride, decyl bromide, lauryl bromide, myristyl bromide, and stearyl bromide, and decyl iodide, lauryl iodide, myristyl iodide, and stearyl iodide; and benzyl bromide and phenethyl bromide.In light of the foregoing, any reference in this specification to a plurality of the disclosed compounds is intended to encompass the plurality of the disclosed compounds and their salts, hydrates, or solvates.

[0140] The present disclosure encompasses the preparation and use of solvates of a plurality of the disclosed compounds. As used herein, the term "solvate" is a combination, physical association, and / or solvation (e.g., di-solvate, mono-solvate, or hemi-solvate, etc.) of a disclosed compound with solvent molecules, and the ratio of solvent molecules to the disclosed compound is about 2:1, about 1:1, or about 1:2, respectively. This physical association involves the variability of ionic and covalent bonds (including hydrogen bonds). In certain instances, a solvate can be isolated, such as when one or more solvent molecules are incorporated into the crystal lattice of a crystalline solid. Thus, "solvate" encompasses both the liquid phase and isolable solvates. A plurality of the disclosed compounds can exist as solvated forms with solvents (such as water, methanol, and ethanol, etc.), and it is intended that the present disclosure encompasses both solvated and non-solvated forms of a plurality of the disclosed compounds.

[0141] One type of solvate is a hydrate. "Hydrate" relates to a specific subgroup 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 a solvate of fluconazole with ethyl acetate and 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 A.L. Bingham et al., Chem. Commun. 603 - 604(2001). A non - limiting and typical process for preparing a solvate would involve dissolving one of the disclosed compounds in a desired solvent (organic, water, or a mixture thereof) at a temperature from 20°C to above about 25°C, then cooling the solution at a rate sufficient to form crystals, and isolating the crystals by known methods (e.g., filtration). Analytical techniques such as infrared spectroscopy can be used to confirm the presence of the solvent in the solvate crystals.

[0142] The use of the terms "a", "an", "the", and similar designators in the context of the description of the present disclosure (especially in the context of the claims) is to be construed to cover both the singular and the plural unless otherwise indicated. The recitation of a range of values herein is merely intended to serve as a convenient method of referring individually to each separate value falling within the range as if it were individually recited 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 merely intended to better illustrate the disclosure and is not a limitation on the scope of the disclosure unless otherwise claimed. No language in the specification should be construed as indicating any non - claimed element as essential to the practice of the disclosure.

[0143] The term "wt / wt%" as used herein, when referring to a component in a composition or blend (e.g., a composition containing one disclosed compound and one or more elastomers; or a composition containing one disclosed composition and one or more fillers; or a blend containing two or more elastomers, etc.), refers to the mass of the component divided by the combined mass of all components in the composition or blend, and then multiplied by 100. For example, the wt / wt% of one disclosed compound in a composition containing 1 kg of the compound, 1 kg of natural rubber, and 2 kg of synthetic rubber is 25 wt / wt% (1 kg / 4 kg = 0.25 × 100 = 25 wt / wt%). The wt / wt% of one disclosed compound in a composition containing 1 kg of the compound and 1 kg of carbon black is 50 wt / wt% (1 kg / 2 kg = 0.20 × 100 = 50 wt / wt%). The wt / wt% of one disclosed compound in a composition containing 1 kg of the compound, 1 kg of natural rubber, 2 kg of synthetic rubber, and 1 kg of carbon black is 20 wt / wt% (1 kg / 5 kg = 0.20 × 100 = 20 wt / wt%). The wt / wt% of natural rubber in a blend of one or more elastomers containing 20 kg of natural rubber and 30 kg of synthetic rubber is 40 wt / wt% (20 kg / 50 kg = 0.40 × 100 = 40 wt / wt%).

[0144] Compositions and Methods of Use In another embodiment, the present disclosure provides (i) one disclosed compound; and (ii) one or more elastomers; or (iii) one or more fillers; or (iv) one or more rubber chemicals; or (v) one or more plasticizers; or (vi) a second antioxidant; or (vii) a combination of one or more elastomers, one or more fillers, one or more rubber chemicals, one or more plasticizers, and / or a second antioxidant and provides a composition comprising the same.

[0145] In some embodiments, one composition of the present disclosure comprises from about 15 wt / wt% to about 85 wt / wt% of one compound of the present disclosure. In some embodiments, the composition is 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%,It contains one compound of the present disclosure in an amount of 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%. In some embodiments, the composition is in an amount of about 0.1 wt / wt% to about 0.5 wt / wt%, about 0.1 wt / wt% to about 1 wt / wt%, about 0.1 wt / wt% to about 1.5 wt / wt%, about 0.1 wt / wt% to about 2 wt / wt%, about 0.1 wt / wt% to about 2.5 wt / wt%, about 0.1 wt / wt% to about 3 wt / wt%, about 0.1 wt / wt% to about 3.5 wt / wt%, about 0.1 wt / wt% to about 4 wt / wt%, about 0.1 wt / wt% to about 4.5 wt / wt%, about 0.1 wt / wt% to about 5 wt / wt%, about 0.1 wt / wt% to about 6 wt / wt%, about 0.1 wt / wt% to about 7 wt / wt%, about 0.1 wt / wt% to about 8 wt / wt%, about 0.1 wt / wt% to about 9 wt / wt%, about 0.1 wt / wt% to about 10 wt / wt%, about 0.5 wt / wt% to about 1 wt / wt%, about 0.5 wt / wt% to about 1.5 wt / wt%, about 0.5 wt / wt% to about 2 wt / wt%, about 0.5 wt / wt% to about 2.5 wt / wt%, about 0.5 wt / wt% to about 3 wt / wt%, about 0.5 wt / wt% to about 3.5 wt / wt%, about 0.5 wt / wt% to about 4 wt / wt%, about 0.5 wt / wt% to about 4.5 wt / wt%, about 0.5 wt / wt% to about 5 wt / wt%, about 0.5 wt / wt% to about 6 wt / wt%, about 0.5 wt / wt% to about 7 wt / wt%, about 0.5 wt / wt% to about 8 wt / wt%, about 0.5 wt / wt% to about 9 wt / wt%, about 0.5 wt / wt% to about 10 wt / wt%, about 1 wt / wt% to about 2 wt / wt%, about 1 wt / wt% to about 2.5 wt / wt%, about 1 wt / wt% to about 3 wt / wt%, about 1 wt / wt% to about 3.5 wt / wt%, about 1 wt / wt% to about 4 wt / wt%, about 1 wt / wt% to about 4.5 wt / wt%, about 1 wt / wt% to about 5 wt / wt%, about 1 wt / wt% to about 6 wt / wt%, about 1 wt / wt% to about 7 wt / wt%, about 1 wt / wt% to about 8 wt / wt%, about 1 wt / wt% to about 9 wt / wt%, about 1 wt / wt% to about 10 wt / wt%,from about 1.5 wt / wt% to about 2 wt / wt%, from about 1.5 wt / wt% to about 2.5 wt / wt%, from about 1.5 wt / wt% to about 3 wt / wt%, from about 1.5 wt / wt% to about 3.5 wt / wt%, from about 1.5 wt / wt% to about 4 wt / wt%, from about 1.5 wt / wt% to about 4.5 wt / wt%, from about 1.5 wt / wt% to about 5 wt / wt%, from about 1.5 wt / wt% to about 6 wt / wt%, from about 1.5 wt / wt% to about 7 wt / wt%, from about 1.5 wt / wt% to about 8 wt / wt%, from about 1.5 wt / wt% to about 9 wt / wt%, from about 1.5 wt / wt% to about 10 wt / wt%, from about 2 wt / wt% to about 2.5 wt / wt%, from about 2 wt / wt% to about 3 wt / wt%, from about 2 wt / wt% to about 3.5 wt / wt%, from about 2 wt / wt% to about 4 wt / wt%, from about 2 wt / wt% to about 4.5 wt / wt%, from about 2 wt / wt% to about 5 wt / wt%, from about 2 wt / wt% to about 6 wt / wt%, from about 2 wt / wt% to about 7 wt / wt%, from about 2 wt / wt% to about 8 wt / wt%, from about 2 wt / wt% to about 9 wt / wt%, from about 2 wt / wt% to about 10 wt / wt%, from about 2.5 wt / wt% to about 3 wt / wt%, from about 2.5 wt / wt% to about 3.5 wt / wt%, from about 2.5 wt / wt% to about 4 wt / wt%, from about 2.5 wt / wt% to about 4.5 wt / wt%, from about 2.5 wt / wt% to about 5 wt / wt%, from about 2.5 wt / wt% to about 6 wt / wt%, from about 2.5 wt / wt% to about 7 wt / wt%, from about 2.5 wt / wt% to about 8 wt / wt%, from about 2.5 wt / wt% to about 9 wt / wt%, from about 2.5 wt / wt% to about 10 wt / wt%, from about 3 wt / wt% to about 4 wt / wt%, from about 3 wt / wt% to about 4.5 wt / wt%, from about 3 wt / wt% to about 5 wt / wt%, from about 3 wt / wt% to about 6 wt / wt%, from about 3 wt / wt% to about 7 wt / wt%, from about 3 wt / wt% to about 8 wt / wt%, from about 3 wt / wt% to about 9 wt / wt%, from about 3 wt / wt% to about 10 wt / wt%, from about 3.5 wt / wt% to about 4 wt / wt%, from about 3.5 wt / wt% to about 4.5 wt / wt%, from about 3.5 wt / wt% to about 5 wt / wt%, from about 3.5 wt / wt% to about 6 wt / wt%, from about 3.5 wt / wt% to about 7 wt / wt%, from about 3.5 wt / wt% to about 8 wt / wt%, from about 3.5 wt / wt% to about 9 wt / wt%, from about 3.5 wt / wt% to about 10 wt / wt%, from about 4 wt / wt% to about 4.5 wt / wt%Comprising one compound of the present disclosure in an amount of about 4 wt / wt% to about 5 wt / wt%, about 4 wt / wt% to about 6 wt / wt%, about 4 wt / wt% to about 7 wt / wt%, about 4 wt / wt% to about 8 wt / wt%, about 4 wt / wt% to about 9 wt / wt%, about 4 wt / wt% to about 10 wt / wt%, about 4.5 wt / wt% to about 5 wt / wt%, about 4.5 wt / wt% to about 6 wt / wt%, about 4.5 wt / wt% to about 7 wt / wt%, about 4.5 wt / wt% to about 8 wt / wt%, about 4.5 wt / wt% to about 9 wt / wt%, about 4.5 wt / wt% to about 10 wt / wt%, about 5 wt / wt% to about 6 wt / wt%, about 5 wt / wt% to about 7 wt / wt%, about 5 wt / wt% to about 8 wt / wt%, about 5 wt / wt% to about 9 wt / wt%, about 5 wt / wt% to about 10 wt / wt%, about 6 wt / wt% to about 7 wt / wt%, about 6 wt / wt% to about 8 wt / wt%, about 6 wt / wt% to about 9 wt / wt%, about 6 wt / wt% to about 10 wt / wt%, about 7 wt / wt% to about 8 wt / wt%, about 7 wt / wt% to about 9 wt / wt%, about 8 wt / wt% to about 10 wt / wt%, about 8 wt / wt% to about 9 wt / wt%, about 8 wt / wt% to about 10 wt / wt%, or about 9 wt / wt% to about 10 wt / wt%.

[0146] In some embodiments, one composition of the present disclosure comprises about 50 wt / wt% of one compound 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 one compound of the present disclosure. In some embodiments, the composition comprises about 0.1 wt / wt%, about 0.5 wt / wt%, about 1 wt / wt%, about 1.5 wt / wt%, about 2 wt / wt%, about 2.5 wt / wt%, about 3 wt / wt%, about 3.5 wt / wt%, about 4 wt / wt%, about 4.5 wt / wt%, about 5 wt / wt%, about 5.5 wt / wt%, about 6 wt / wt%, about 6.5 wt / wt%, about 7 wt / wt%, about 7.5 wt / wt%, about 8 wt / wt%, about 8.5 wt / wt%, about 9 wt / wt%, or about 10 wt / wt% of one compound of the present disclosure.

[0147] In some embodiments, one composition of the present disclosure comprises Compound 1, Compound 2, Compound 4, Compound 5, or Compound 6, Compound 11, Compound 19, Compound 27, Compound 30, Compound 31, or Compound 32.

[0148] In another embodiment, one composition of the present disclosure comprises one compound of the present disclosure and one or more elastomers.

[0149] As used herein, the term "elastomer" typically refers to a polymer having viscoelasticity with low intermolecular forces, a low Young's modulus, and high fracture strain (i.e., having both viscosity and elasticity). Elastomers can typically be crosslinked by heating (a process called curing or vulcanization) in the presence of one or more crosslinking agents. Rubber is one type of elastomer. Non-limiting types of rubber include natural rubber (NR), synthetic rubbers, and blends thereof. As used herein, the term "natural rubber" refers to a naturally occurring elastomer that can be obtained from rubber trees of the genus Hevea. Non-limiting types of synthetic rubbers include unsaturated rubbers, saturated rubbers, rubbers having substituents of fluoro, fluoroalkyl, or fluoroalkoxy on the polymer chain (FKM), silicone rubbers (Q), and blends thereof. Non-limiting examples of unsaturated rubbers include isoprene rubber (IR), butyl rubber (IIR), butadiene rubber (BR), styrene-isoprene-butadiene rubber (SIBR), styrene-butadiene rubber (SBR), nitrile butadiene rubber (NBR), chloroprene rubber (CR), ethylene propylene diene rubber (EPDM), and blends thereof. These unsaturated rubbers undergo cyclization and crosslinking reactions that lead to hardening of the aged portion. As oxidation occurs, these vulcanizates harden and ultimately become brittle products. Partial oxidation of vulcanizates when used in applications such as vehicle tire sidewalls leads to loss of performance. Saturated rubbers are rubbers that do not contain C=C unsaturation and include, but are not limited to, acrylic rubber (ACM), chlorinated polyethylene (CM), chlorosulfonated polyethylene (CSM), polychloromethyloxirane (CO), ethylene-ethyl acrylate copolymer (EAM), epichlorohydrin rubber (ECO), ethylene propylene rubber (EPM), ethylene vinyl acetate copolymer (EVM), rubbers having substituents of fluoro, fluoroalkyl, or fluoroalkoxy on the polymer chain (FKM), silicone rubbers (Q), and blends thereof.

[0150] In some embodiments, the natural rubber includes rubber derived from alternative rubber plants. The term "natural rubber includes rubber derived from alternative rubber plants" as used herein refers to naturally occurring elastomers that can be obtained from "non-Hevea" sources. In some embodiments, the alternative rubber plants are Parthenium argentatum (guayule) or Taraxacum kok-saghyz (Russian dandelion).

[0151] In some embodiments, the one or more elastomers further include recycled rubber. The term "recycled rubber" as used herein refers to elastomers recycled from scrap materials (such as used tires).

[0152] In some embodiments, one composition of the present disclosure comprises from about 15 wt / wt% to about 85 wt / wt% of one or more elastomers. In some embodiments, the composition is 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%,It contains one or more elastomers of 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%.

[0153] In some embodiments, a composition of the present disclosure contains about 50 wt / wt% of one or more elastomers. In some embodiments, the composition contains 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.

[0154] The term "phr" as used herein refers to parts per 100 parts by weight of rubber. The parts by weight of an individual component are based on 100 parts by weight of the total mass of one or more elastomers present in the composition.

[0155] In some embodiments, one composition of the present disclosure comprises from about 1 phr to about 5 phr of one compound of the present disclosure. In some embodiments, the composition comprises from about 0.01 phr to about 0.1 phr, from about 0.01 phr to about 0.5 phr, from about 0.01 phr to about 1 phr, from about 0.01 phr to about 2 phr, from about 0.01 phr to about 3 phr, from about 0.01 phr to about 4 phr, from about 0.01 phr to about 5 phr, from about 0.01 phr to about 7.5 phr, from about 0.01 phr to about 10 phr, from about 0.01 phr to about 20 phr, from about 0.1 phr to about 0.5 phr, from about 0.1 phr to about 1 phr, from about 0.1 phr to about 2 phr, from about 0.1 phr to about 3 phr, from about 0.1 phr to about 4 phr, from about 0.1 phr to about 5 phr, from about 0.1 phr to about 7.5 phr, from about 0.1 phr to about 10 phr, from about 0.1 phr to about 20 phr, from about 1 phr to about 2 phr, from about 1 phr to about 3 phr, from about 1 phr to about 4 phr, from about 1 phr to about 7.5 phr, from about 1 phr to about 10 phr, from about 1 phr to about 20 phr, from about 2 phr to about 3 phr, from about 2 phr to about 4 phr, from about 2 phr to about 5 phr, from about 2 phr to about 7.5 phr, from about 2 phr to about 10 phr, from about 2 phr to about 20 phr, from about 3 phr to about 4 phr, from about 3 phr to about 5 phr, from about 3 phr to about 7.5 phr, from about 3 phr to about 10 phr, from about 3 phr to about 20 phr, from about 4 phr to about 5 phr, from about 4 phr to about 7.5 phr, from about 4 phr to about 10 phr, from about 4 phr to about 20 phr, from about 5 phr to about 7.5 phr, from about 5 phr to about 10 phr, from about 5 phr to about 20 phr, from about 7.5 phr to about 10 phr, from about 7.5 phr to about 20 phr, or from about 10 phr to about 20 phr of one compound of the present disclosure.

[0156] In some embodiments, one composition of the present disclosure comprises about 3 phr of one compound of the present disclosure. In some embodiments, the composition comprises about 0.01 phr, about 0.1 phr, about 0.5 phr, about 1 phr, about 2 phr, about 3 phr, about 4 phr, about 5 phr, about 7.5 phr, about 10 phr, or about 20 phr of one compound of the present disclosure.

[0157] In some embodiments, a composition of the present disclosure comprises a compound of the present disclosure and one or more fillers.

[0158] As used herein, the term "filler" is a substance that reinforces an elastomeric composition or imparts other properties to the elastomeric composition, including but not limited to amplification of the volume of the composition. Non-limiting examples of fillers include carbon black, silica, kaolin, calcium silicate, talc, carbon nanotubes (CNT), carbon fibers (HCF), graphite, graphene, aluminosilicate, starch, and fibers, and combinations thereof.

[0159] In some embodiments, the filler is derived from a natural source. For example, silica may be derived from rice husks.

[0160] In some embodiments, a composition of the present disclosure comprises from about 15 wt / wt% to about 85 wt / wt% of one or more fillers. In some embodiments, the composition is 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%,It contains one or more fillers in an amount of 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%.

[0161] In some embodiments, one composition of the present disclosure contains about 50 wt / wt% of one or more fillers. In some embodiments, the composition contains one or more fillers in an amount of 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%.

[0162] In some embodiments, a composition of the present disclosure comprises one or more fillers in an amount of from about 30 phr to about 500 phr. In some embodiments, the composition comprises one or more fillers in an amount of from about 30 phr to about 50 phr, from about 30 phr to about 100 phr, from about 30 phr to about 150 phr, from about 30 phr to about 200 phr, from about 30 phr to about 250 phr, from about 30 phr to about 300 phr, from about 30 phr to about 350 phr, from about 30 phr to about 400 phr, from about 30 phr to about 450 phr, from about 30 phr to about 500 phr, from about 50 phr to about 100 phr, from about 50 phr to about 150 phr, from about 50 phr to about 200 phr, from about 50 phr to about 250 phr, from about 50 phr to about 300 phr, from about 50 phr to about 350 phr, from about 50 phr to about 400 phr, from about 50 phr to about 450 phr, from about 50 phr to about 500 phr, from about 100 phr to about 150 phr, from about 100 phr to about 200 phr, from about 100 phr to about 250 phr, from about 100 phr to about 300 phr, from about 100 phr to about 350 phr, from about 100 phr to about 400 phr, from about 100 phr to about 450 phr, from about 100 phr to about 500 phr, from about 150 phr to about 200 phr, from about 150 phr to about 250 phr, from about 150 phr to about 300 phr, from about 150 phr to about 350 phr, from about 150 phr to about 400 phr, from about 150 phr to about 450 phr, from about 150 phr to about 500 phr, from about 200 phr to about 250 phr, from about 200 phr to about 300 phr, from about 200 phr to about 350 phr, from about 200 phr to about 400 phr, from about 200 phr to about 450 phr, from about 200 phr to about 500 phr, from about 250 phr to about 300 phr, from about 250 phr to about 350 phr, from about 250 phr to about 400 phr, from about 250 phr to about 450 phr, from about 250 phr to about 500 phr, from about 300 phr to about 350 phr, from about 300 phr to about 400 phr, from about 300 phr to about 450 phr, from about 300 phr to about 500 phr, from about 350 phr to about 400 phr, from about 350 phr to about 450 phr, from about 350 phr to about 500 phr, from about 400 phr to about 450 phr, from about 400 phr to about 500 phr, or from about 450 phr to about 500 phr.

[0163] In some embodiments, a composition of the present disclosure comprises one or more fillers at about 300 phr. In some embodiments, the composition comprises one or more fillers at 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.

[0164] In some embodiments, a composition of the present disclosure comprises a compound of the present disclosure and one or more rubber chemicals. The term "rubber chemical" as used herein refers to a compound or substance used to facilitate the vulcanization of rubber. Rubber chemicals include, but are not limited to, vulcanizing agents, accelerators, activators, and scorch inhibitors.

[0165] The term "vulcanization" as used herein refers to the process by which crosslinks are formed between elastomers to achieve a change in the material properties of the elastomers. In particular, vulcanization typically increases the stiffness and durability of the elastomers. Vulcanization is carried out at room temperature or elevated temperature depending on the nature of the elastomer(s), filler(s), and rubber chemical(s) being used. The term "curing" is also used in the art to describe this process.

[0166] The term "vulcanizing agent" as used herein refers to any substance that enables crosslinking between elastomers. Vulcanizing agents can enable crosslinking between separated polymer chains of an elastomer by various mechanisms (including, but not limited to, formation of covalent bonds between the vulcanizing agent and two or more separated polymer chains, or generation of radical species on separated polymer chains that can combine to form a covalent bond between two polymer chains). Non-limiting examples of vulcanizing agents include sulfur, peroxides, vulcanized vegetable oils, factices, and resins. Non-limiting examples of sulfur include octasulfur (S8), cyclododecasulfur (S 12) and polymeric sulfur. Non-limiting examples of peroxides include benzoyl peroxide, dicumyl peroxide (DC), 2,5-dimethyl-2,5-di-(tert-butylperoxy)-3-hexyne (2,5Tri), 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 bonding resin. The term "bonding resin" as used herein refers to a chemical substance (such as resorcinol formaldehyde resin and phenolic resin) that reacts with a methylene donor (such as hexamethylenetetramine (HMTA) or hexamethoxymethylmelamine (HMMM)) to enhance adhesion.

[0167] The term "accelerator", as used herein, refers to any substance that increases the rate of vulcanization. In some embodiments, the accelerator enables vulcanization to be carried out at a lower temperature and / or enables more efficient use of a vulcanizing agent (e.g., sulfur). Non-limiting examples of accelerators include guanidine, thiazole, sulfenamide, thiuram, dithiocarbamate, xanthate, and thiophosphate. Non-limiting examples of guanidine include diphenylguanidine (DPG). Non-limiting examples of thiazole include 2-mercaptobenzothiazole (MBT), zinc 2-mercaptobenzothiazole (ZMBT), mercaptobenzothiazole disulfide (MBTS), and N-tert-butyl-2-benzothiazolesulfenimide (TBSI). Non-limiting examples of sulfenamide include N-tert-butyl-2-benzothiazylsulfenamide (TBBS), N-cyclohexylbenzothiazole-2-sulfenamide (CBS), dicyclohexyl-2-benzothiazolesulfenamide (DCBS), N-oxydiethylene benzothiazole sulfenamide (OBTS), N-oxydiethylene thiocarbamyl-N'-oxydiethylene sulfenamide (OTOS), and thiocarbamyl sulfenamide. Non-limiting examples of thiuram include dimethylcarbamothioic dithio peroxide anhydride (thiuram), dipentamethylene thiuram tetrasulfide (DPIT), tetrabenzylthiuram disulfide (TBzTD), tetraethylthiuram disulfide (TETD), tetramethylthiuram disulfide (TMTD), and tetramethylthiuram sulfide (TMTM). Non-limiting examples of dithiocarbamate include zinc dimethyldithiocarbamate (ZDMC), zinc diethyldithiocarbamate (ZDEC), zinc dibutyldithiocarbamate (ZDBC), nickel dibutyldithiocarbamate (NDBC), sodium dibenzyldithiocarbamate (SBEC), sodium diethyldithiocarbamate (SDEC), tellurium diethyldithiocarbamate (TDEC), and zinc dibenzyldithiocarbamate (ZEBC).

[0168] When used herein, the term "activator" refers to any substance that activates a vulcanizing agent and enables the vulcanizing agent to crosslink an elastomer as described above. The activator can act via various mechanisms (including, but not limited to, formation of a chemical complex with an accelerator or coordination to 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. A non-limiting example of a metal complex is zinc ethylhexanoate.

[0169] When used herein, the term "scorching inhibitor" refers to a compound that delays the start and / or rate of vulcanization. These compounds are also referred to as "retarders". Non-limiting examples of scorching inhibitors include N-(cyclohexylthio)phthalimide (CTP), benzoic anhydride, salicylic anhydride, and phthalic anhydride.

[0170] In some embodiments, one composition of the present disclosure comprises one or more rubber chemicals in an amount of from about 15 wt / wt% to about 85 wt / wt%. In some embodiments, the composition is 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%,It contains one or more rubber chemicals in an amount of 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%.

[0171] In some embodiments, a composition of the present disclosure contains about 15 wt / wt% of one or more rubber chemicals. In some embodiments, the composition contains 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.

[0172] In some embodiments, one composition of the present disclosure comprises one or more rubber chemicals in an amount of from about 1 phr to about 20 phr. In some embodiments, the composition comprises one or more rubber chemicals in an amount of from about 0.1 phr to about 1 phr, from about 0.1 phr to about 5 phr, from about 0.1 phr to about 10 phr, from about 0.1 phr to about 15 phr, from about 0.1 phr to about 20 phr, from about 0.1 phr to about 25 phr, from about 0.1 phr to about 30 phr, from about 0.1 phr to about 35 phr, from about 0.1 phr to about 40 phr, from about 1 phr to about 5 phr, from about 1 phr to about 10 phr, from about 1 phr to about 15 phr, from about 1 phr to about 25 phr, from about 1 phr to about 30 phr, from about 1 phr to about 35 phr, from about 1 phr to about 40 phr, from about 5 phr to about 10 phr, from about 5 phr to about 15 phr, from about 5 phr to about 20 phr, from about 5 phr to about 25 phr, from about 5 phr to about 30 phr, from about 5 phr to about 35 phr, from about 5 phr to about 40 phr, from about 10 phr to about 15 phr, from about 10 phr to about 20 phr, from about 10 phr to about 25 phr, from about 10 phr to about 30 phr, from about 10 phr to about 35 phr, from about 10 phr to about 40 phr, from about 15 phr to about 20 phr, from about 15 phr to about 25 phr, from about 15 phr to about 30 phr, from about 15 phr to about 35 phr, from about 15 phr to about 40 phr, from about 20 phr to about 25 phr, from about 20 phr to about 30 phr, from about 20 phr to about 35 phr, from about 20 phr to about 40 phr, from about 25 phr to about 30 phr, from about 25 phr to about 35 phr, from about 25 phr to about 40 phr, from about 30 phr to about 35 phr, from about 30 phr to about 40 phr, or from about 35 phr to about 40 phr.

[0173] In some embodiments, one composition of the present disclosure comprises one or more rubber chemicals in an amount of about 10 phr. In some embodiments, the composition comprises one or more rubber chemicals in an amount of 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.

[0174] The term "plasticizer", as used herein, refers to a processing aid used to reduce viscosity, increase plasticity, and / or expand the volume of a composition. Plasticizers facilitate the process of mixing and forming a composition containing 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 oils of natural origin (such as soybean oil, vegetable oil, or orange oil).

[0175] In some embodiments, one composition of the present disclosure comprises one or more plasticizers in an amount of from about 15 wt / wt% to about 85 wt / wt%. In some embodiments, the composition is 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%,It contains one or more plasticizers in an amount of 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%.

[0176] In some embodiments, a composition of the present disclosure contains one or more plasticizers in an amount of about 15 wt / wt%. In some embodiments, the composition contains one or more plasticizers in an amount of 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%.

[0177] In some embodiments, one composition of the present disclosure comprises one or more plasticizers in an amount of from about 1 phr to about 20 phr. In some embodiments, the composition comprises one or more plasticizers in an amount of from about 0.1 phr to about 1 phr, from about 0.1 phr to about 5 phr, from about 0.1 phr to about 10 phr, from about 0.1 phr to about 15 phr, from about 0.1 phr to about 20 phr, from about 0.1 phr to about 25 phr, from about 0.1 phr to about 30 phr, from about 0.1 phr to about 35 phr, from about 0.1 phr to about 40 phr, from about 1 phr to about 5 phr, from about 1 phr to about 10 phr, from about 1 phr to about 15 phr, from about 1 phr to about 25 phr, from about 1 phr to about 30 phr, from about 1 phr to about 35 phr, from about 1 phr to about 40 phr, from about 5 phr to about 10 phr, from about 5 phr to about 15 phr, from about 5 phr to about 20 phr, from about 5 phr to about 25 phr, from about 5 phr to about 30 phr, from about 5 phr to about 35 phr, from about 5 phr to about 40 phr, from about 10 phr to about 15 phr, from about 10 phr to about 20 phr, from about 10 phr to about 25 phr, from about 10 phr to about 30 phr, from about 10 phr to about 35 phr, from about 10 phr to about 40 phr, from about 15 phr to about 20 phr, from about 15 phr to about 25 phr, from about 15 phr to about 30 phr, from about 15 phr to about 35 phr, from about 15 phr to about 40 phr, from about 20 phr to about 25 phr, from about 20 phr to about 30 phr, from about 20 phr to about 35 phr, from about 20 phr to about 40 phr, from about 25 phr to about 30 phr, from about 25 phr to about 35 phr, from about 25 phr to about 40 phr, from about 30 phr to about 35 phr, from about 30 phr to about 40 phr, or from about 35 phr to about 40 phr.

[0178] In some embodiments, one composition of the present disclosure comprises one or more plasticizers in an amount of about 10 phr. In some embodiments, the composition comprises one or more plasticizers in an amount of 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.

[0179] In some embodiments, a composition of the present disclosure further comprises a second anti-degradant that is not a compound of the present disclosure. In some embodiments, the second anti-degradant is an antioxidant. In some embodiments, the second anti-degradant is an anti-ozone degradation agent. Non-limiting examples of anti-degradants include paraphenylenediamine (PPD), trimethyl-dihydroquinoline (TMQ), phenols, alkylated diphenylamine (DPA), diphenylamine-ketone condensates, and natural anti-degradants. Non-limiting examples of PPD include 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 -(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 TMQ include 2,2,4-trimethyl-1,2-dihydroquinoline and its oligomers or polymers.

[0180] In some embodiments, one composition of the present disclosure comprises from about 15 wt / wt% to about 85 wt / wt% of a second anti-degradant. In some embodiments, the composition comprises from about 1 wt / wt% to about 5 wt / wt%, from about 1 wt / wt% to about 15 wt / wt%, from about 1 wt / wt% to about 25 wt / wt%, from about 1 wt / wt% to about 35 wt / wt%, from about 1 wt / wt% to about 45 wt / wt%, from about 1 wt / wt% to about 55 wt / wt%, from about 1 wt / wt% to about 65 wt / wt%, from about 1 wt / wt% to about 75 wt / wt%, from about 1 wt / wt% to about 85 wt / wt%, from about 1 wt / wt% to about 95 wt / wt%, from about 5 wt / wt% to about 15 wt / wt%, from about 5 wt / wt% to about 25 wt / wt%, from about 5 wt / wt% to about 35 wt / wt%, from about 5 wt / wt% to about 45 wt / wt%, from about 5 wt / wt% to about 55 wt / wt%, from about 5 wt / wt% to about 65 wt / wt%, from about 5 wt / wt% to about 75 wt / wt%, from about 5 wt / wt% to about 85 wt / wt%, from about 5 wt / wt% to about 95 wt / wt%, from about 15 wt / wt% to about 25 wt / wt%, from about 15 wt / wt% to about 35 wt / wt%, from about 15 wt / wt% to about 45 wt / wt%, from about 15 wt / wt% to about 55 wt / wt%, from about 15 wt / wt% to about 65 wt / wt%, from about 15 wt / wt% to about 75 wt / wt%, from about 15 wt / wt% to about 95 wt / wt%, from about 25 wt / wt% to about 35 wt / wt%, from about 25 wt / wt% to about 45 wt / wt%, from about 25 wt / wt% to about 55 wt / wt%, from about 25 wt / wt% to about 65 wt / wt%, from about 25 wt / wt% to about 75 wt / wt%, from about 25 wt / wt% to about 85 wt / wt%, from about 25 wt / wt% to about 95 wt / wt%, from about 35 wt / wt% to about 45 wt / wt%, from about 35 wt / wt% to about 55 wt / wt%, from about 35 wt / wt% to about 65 wt / wt%, from about 35 wt / wt% to about 75 wt / wt%, from about 35 wt / wt% to about 85 wt / wt%, from about 35 wt / wt% to about 95 wt / wt%, from about 45 wt / wt% to about 55 wt / wt%, from about 45 wt / wt% to about 65 wt / wt%, from about 45 wt / wt% to about 75 wt / wt%, from about 45 wt / wt% to about 85 wt / wt%, from about 45 wt / wt% to about 95 wt / wt%, from about 55 wt / wt% to about 65 wt / wt%, from about 55 wt / wt% to about 75 wt / wt%, from about 55 wt / wt% to about 85 wt / wt%,It contains a second decomposition inhibitor of 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%.

[0181] In some embodiments, one composition of the present disclosure contains about 15 wt / wt% of the second decomposition inhibitor. In some embodiments, the composition contains 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 decomposition inhibitor.

[0182] In some embodiments, one composition of the present disclosure contains about 1 to about 5 phr of the second decomposition inhibitor. In some embodiments, the composition contains 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.

[0183] In some embodiments, one composition of the present disclosure comprises about 3 phr of a second anti-degradant. 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 anti-degradant.

[0184] In some embodiments, the present disclosure provides a composition comprising one compound of the present disclosure and one or more carriers. The term "carrier" as used herein refers to a solid that can adsorb a liquid while retaining the general properties of a solid at room temperature. In some embodiments, the carrier is an inert material. In some embodiments, the carrier has a high surface area. In some embodiments, the carrier comprises particles having a diameter of less than 500 microns.

[0185] In some embodiments, the composition comprises one or more carriers in an amount of from about 15 wt / wt% to about 85 wt / wt%. In some embodiments, the composition is 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%,Comprising one or more carriers of 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%.

[0186] In some embodiments, the composition comprises one or more carriers of about 15 wt / wt%. In some embodiments, the composition comprises one or more carriers of 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%.

[0187] The present disclosure also provides a process for preparing a composition comprising a compound of the present disclosure and one or more carriers, the process comprising mixing the compound and the one or more carriers.

[0188] The present disclosure also provides a lubricant composition comprising a compound of the present disclosure and a lubricant. Non-limiting examples of lubricants include mineral oils, high molecular weight petroleum distillates (such as naphthenic distillates, aromatic distillates, and paraffinic distillates), synthetic oils (such as polyalpha-olefins (PAO), synthetic esters, polyalkylene glycols (PAG), phosphate esters, perfluoropolyethers (PFPE), alkylated naphthalenes (AN), silicate esters, ionic liquids, and multiply alkylated cyclopentanes (MAC)), solid lubricants (such as polytetrafluoroethylene (PTFE), graphite, hexagonal boron nitride, molybdenum disulfide, tungsten disulfide), water-soluble lubricants (such as hydrated brush-type polymers), and biological lubricants (such as triglyceride esters, high oleic acid canola oil, castor oil, coconut oil, sunflower oil, and rapeseed oil).

[0189] The present disclosure also provides a combustible fuel composition comprising a combustible fuel and one compound of the present disclosure. Non-limiting examples of combustible fuels include gasoline, diesel, kerosene, liquefied petroleum gas, synthetic fuels, and biodiesel.

[0190] The present disclosure also provides a fuel additive composition comprising a fuel additive and one compound of the present disclosure. Non-limiting examples of fuel additives include alcohols, ethers, antioxidants, stabilizers, detergents, antiknock agents, lead scavengers, fuel dyes, viscosity modifiers, and oxygenates such as butyl rubber. In some embodiments, the butyl rubber is in the form of polyisobutylene succinimide. In some embodiments, the butyl rubber is added as a detergent to prevent clogging of diesel fuel injectors.

[0191] Vulcanized elastomer article The present disclosure also provides a vulcanized elastomer article comprising one compound of the present disclosure. The term "vulcanized elastomer article" refers to an article made by forming a composition comprising an elastomer into a specific shape and vulcanizing the composition to provide the article.

[0192] The present disclosure also provides a vulcanized elastomer article prepared using the compositions described herein.

[0193] In some embodiments, the vulcanized elastomer article is a tire. In some embodiments, the tire is a passenger car tire, a light truck tire, a heavy truck or bus tire, a motorcycle tire, an agricultural tire, a construction machinery tire, an aircraft tire, or a racing tire.

[0194] In some embodiments, the vulcanized elastomeric article is a component of a tire. In some embodiments, the component is a bead, belt, body ply, inner liner, sidewall, undertread, or tread.

[0195] In some embodiments, the vulcanized elastomeric article is a rubber overshoe, sealing strip, sound absorbing panel, air spring, bellows, membrane, tactile sensor, safety pad, hose, conveyor belt, or flooring.

[0196] Process The present disclosure is a process for preparing a vulcanized elastomeric article, (a) forming the composition described herein into a shaped form; (b) vulcanizing the shaped form to provide a vulcanized elastomeric article, and the process is also provided.

[0197] In some embodiments, the vulcanization is carried out at an average temperature of about 140 °C to about 160 °C. In some embodiments, the vulcanization is carried out 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.

[0198] In some embodiments, the vulcanization is carried out at an average temperature of about 150 °C. In some embodiments, the vulcanization is carried out 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.

[0199] The present disclosure is a process for retreading a tire, comprising: (a) applying a composition as described herein to the tire; (b) disposing a pre-vulcanized tread around the tire; (c) disposing a curing envelope around the tire; (d) vulcanizing the tire, and also provides said process.

[0200] Kit The present disclosure also provides a kit comprising a composition as described herein, packaged, for example, in a container, in a manner that facilitates the use of the composition in practicing the processes and / or methods of the present disclosure. In some embodiments, the kit includes the composition as described herein and instructions for using the composition in a vulcanizable elastomeric composition. In some embodiments, the kit includes the composition as described herein and instructions for using the composition to prepare a vulcanized elastomeric article. The composition may be packaged in any suitable container (such as a sealed bottle or container), and a label describing the composition and its proper use is affixed to the container or included in the kit.

[0201] The present disclosure also provides the following specific embodiments. Embodiment I. A compound having the formula (I):

Chemical formula

[0202] Embodiment II. X is -CHR 3a The compound according to Embodiment I, wherein it is -

[0203] Embodiment III. R 3a The compound according to Embodiment I or II, wherein R is selected from the group consisting of optionally substituted phenyl, optionally substituted 5- or 6-membered heterocycle, and optionally substituted 5- or 6-membered heteroaryl.

[0204] Embodiment IV. R 3a is

Chemical formula

[0205] Embodiment V. The compound according to Embodiment I, wherein X is -NH-.

[0206] Embodiment VI. The compound according to Embodiment I, wherein X is -O-.

[0207] Embodiment VII. The compound according to Embodiment I, wherein X is -S-.

[0208] Embodiment VIII. R 1 is C1-C 12 alkyl or -CHR 1a R 1b and R 2 is C1-C 12 alkyl or -CHR 2a R 2b The compound according to any one of Embodiments I to VII.

[0209] Embodiment IX. R 1a and R 2a are

Chemical formula

[0210] R 1b and R 2b are hydrogen, a compound according to Embodiment VIII.

[0211] Embodiment X. R 1 and R 2 are isopropyl, a compound according to Embodiment VIII.

[0212] Embodiment XI. (i) A compound according to any one of Embodiments I to X; and (ii) One or more elastomers; or (iii) One or more fillers; or (iv) One or more rubber chemicals; or (v) One or more plasticizers; or (vi) A second antioxidant; or (vii) A combination of one or more elastomers, one or more fillers, one or more rubber chemicals, one or more plasticizers, and / or a second antioxidant, comprising a composition.

Examples

[0213] Example 1 Synthesis of bis(2,2,4-trimethyl-1,2-dihydroquinolin-6-yl)methane (Compound 1)

Chemical formula

[0214] Example 2 Synthesis of bis(2,2,4-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)methane (Compound 2) [Chemical formula] A 300 mL Paar autoclave was charged with crude compound 1 (1.0 g; <2.79 mmol), methanol (77 mL), 37% aqueous HCl (0.46 mL; 5.58 mmol), and wet 10% Pd / C (1.0 g). The autoclave was sealed and then purged with 20 PSI of nitrogen gas. The vessel was charged with 50 PSI of H2 and the reaction mixture was stirred at 25 °C for 1 h. After completion of the reaction, the reaction contents were filtered through a 0.5 μm frit to separate the catalyst residue from the product. Volatiles were removed from the filtrate under reduced pressure (rotary evaporator; water bath = 50 °C). The crude hydrogenated material as the dihydrochloride was dissolved in chloroform. The emerald green solution was transferred to a separatory funnel, washed with saturated aqueous NaHCO3, dried over anhydrous MgSO4, filtered, and volatiles were removed under reduced pressure (rotary evaporator; water bath = 50 °C). Drying was continued to a constant weight to afford the desired product as a greenish-yellow viscous liquid. Representative 1 H and 13 C NMR spectra are shown in Figures 2(a) and 2(b).

[0215] Example 3 Synthesis of 4,4'-(furan-2-ylmethylene)bis(N-isopropylaniline) (Compound 3)

Chemical formula

[0216] Example 4 Synthesis of 4,4’-(furan - 2 - ylmethylene)bis(N-(furan - 2 - ylmethyl)aniline (Compound 7) [Chemical formula] A solution of N,N-dibenzylaniline (42.58 g, 156.120 mmol, 2.14 equiv), furfural (7.00 g, 72.9 mmol, 1.0 equiv), and p-toluenesulfonic acid monohydrate (9.89 g, 51.982 mmol, 0.7 equiv) in toluene (100 mL) was heated at 110 °C overnight. The reaction was cooled to room temperature and diluted with dichloromethane (300 mL). The mixture was washed with saturated sodium bicarbonate (100 mL), and the organic layer was concentrated under reduced pressure. The residue was dry loaded onto silica (70 g) and purified on an Interchim automated chromatography system (2 × 350 g stacked prepack 20 mm silica column) eluting with a gradient of 0–20% ethyl acetate in heptane to afford the intermediate compound 7-I (19.9 g, 44% yield) as a white solid.

[0217] A suspension of compound 7-I (47.0 g, 75.22 mmol, 1.0 equiv) and 5% palladium on carbon (2.35 g, wetted with 50% water) in a 1:1 mixture of methanol (235 mL) and THF (235 mL, 5 volumes) was hydrogenated at 25 psi for 2 h. Upon completion, the reaction was filtered through Celite (30 g) and washed with methanol (200 mL). The filtrate was concentrated under reduced pressure. The residue was dry loaded onto silica gel (50 g) and purified on an Interchim automated chromatography system (220 g, prepack 60 mm silica column) eluting with a gradient of 25–100% ethyl acetate in heptane to afford compound 7-II (13.7 g, 69% yield) as an off-white solid and 4,4'-((tetrahydrofuran-2-yl)methylene)dianiline (2.1 g, 10% yield) as an off-white solid.

[0218] A solution of compound 7-II (13.7 g, 51.83 mmol, 1.0 equiv) and furfural (9.96 g, 103.66 mmol, 2.0 equiv) in dichloromethane (360 mL, 36 volumes) was stirred for 1 hour. Sodium triacetoxyborohydride (30.76 g, 145.123 mmol, 2.8 equiv) was added at room temperature and the reaction was stirred for 1 hour. Completion of the reaction was indicated by LCMS and NMR analysis. The reaction was quenched with saturated sodium bicarbonate (360 mL) and stirred for 1 hour. The layers were separated and the aqueous layer was extracted with dichloromethane (2 x 130 mL). The combined organics were washed with saturated brine (130 mL) and concentrated under reduced pressure. The residue was then dry loaded onto silica (40 g) and purified on an Interchim automated chromatography system (250 g, prepack 60 μm silica column) eluting with a gradient of 0 - 30% ethyl acetate in heptane. The fractions containing the pure product were then concentrated under reduced pressure and dried under high vacuum at 50 °C overnight to afford compound 7 (18.3 g, 83% yield, >95% HPLC purity) as an off-white oil. 1 H NMR (400 MHz, DMSO-d6) δ = 7.58 - 7.51 (m, 3H), 6.86 (d, J = 8.6 Hz, 4H), 6.66 - 6.50 (m, 4H), 6.40 - 6.33 (m, 3H), 6.28 (dd, J = 0.7, 3.2 Hz, 2H), 6.01 - 5.86 (m, 3H), 5.19 - 5.12 (m, 1H), 4.20 (d, J = 6.0 Hz, 4H); 13 C (100 MHz, DMSO-d6) δ = 158.52, 153.93, 147.23, 142.31, 142.19, 130.74, 129.16, 112.61, 110.81, 110.58, 107.42, 107.27, 48.94; MS (ESI) m / z [M+H] + C 27 H 24 Calculated for N2O3, 425.2, found, 425.2.

[0219] Example 5 Synthesis of 4,4’-Methylenebis(N-(furan-2-ylmethyl)aniline) (Compound 8)

Chemical formula

[0220] Example 6 Synthesis of 4,4'-(phenylmethylene)bis(N-isopropylaniline) (Compound 16)

Chemical formula

[0221] p-Toluenesulfonic acid monohydrate (32.6 g, 171.4 mmol, 0.6 eq) was added to a solution of Compound 8-I (64 g, 285.7 mmol, 1 eq) and benzaldehyde (18.2 g, 171.4 mmol, 0.6 eq) in toluene (500 mL). The reaction mixture was refluxed for 24 h equipped with a Dean-Stark apparatus, at which point LC / MS analysis indicated that the conversion from Compound 8-I to Compound 8-II was 65%. After cooling to room temperature, most of the toluene was removed under reduced pressure. The residue was diluted with ethyl acetate (1.5 L). The resulting mixture was washed successively with saturated sodium bicarbonate (2 × 1 L) and saturated brine (2 × 1 L). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to remove three quarters of the solvent. The remaining solution was added to methanol (1.5 L) over 10 min with vigorous stirring. The resulting precipitate was filtered and then triturated with a 10:1 mixture of methanol and ethyl acetate (3 × 300 mL) for 2 h to afford Compound 8-II (25 g, 32% yield, >95% HPLC purity) as an off-white solid.

[0222] Compound 8-II (25 g, 70 mmol, 1 eq) and 10% palladium on carbon (2.5 g, 50% water-wetted) were hydrogenated at 30 psi at room temperature for 2.5 h in a 10:1 mixture of tetrahydrofuran and methanol (300 mL), at which point LC / MS analysis indicated that the reaction was complete. The reaction mixture was filtered through Celite (20 g) and washed with tetrahydrofuran (200 mL). The filtrate was concentrated under reduced pressure. The residue was purified by silica gel (800 g) eluting with a gradient of 5–15% ethyl acetate in heptane to afford Compound 8 (12 g, 72% yield, >95% HPLC purity) as a colorless oil, which gradually solidified as a white solid over 2 days. 11H NMR (400 MHz, CDCl3) δ = 7.34 - 7.08 (m, 5H), 6.92 - 6.86 (m, 4H), 6.51 - 6.46 (m, 4H), 5.32 - 5.27 (m, 1H), 3.57 (spt, J = 6.3 Hz, 2H), 3.35 (s, 2H), 1.18 (d, J = 6.4 Hz, 12H); 13 13C NMR (100 MHz, CDCl3) δ = 145.70, 145.56, 133.25, 130.19, 129.42, 128.05, 125.77, 113.01, 55.21, 44.37, 23.15; MS (ESI) m / z [M+H] + C 25 H 30 Calculated for C21H28N2, 359.2, Found, 359.2.

[0223] Example 7 Synthesis of 4,4’-methylenebis(N-isopropyl aniline) (Compound 19)

Chemical Structure

[0224] Example 8 Synthesis of 4,4'-methylenebis(N-(1-(furan-2-yl)ethyl)aniline) (Compound 20) [Chemical formula] 4,4'-Methylenedianiline (19.8 g, 100 mmol, 1 equivalent) was added to a solution of 2-furyl methyl ketone (27.5 g, 250 mmol, 2.5 equivalents) and titanium(IV) isopropoxide (28.4 g, 100 mmol, 1 equivalent) in methanol (200 mL), followed by the addition of sodium cyanoborohydride (18.9 g, 300 mmol, 3 equivalents). The mixture was refluxed for 3 days. After cooling to room temperature, sodium borohydride (about 1.6 g) was added in portions until 2-furyl methyl ketone 2 disappeared by TLC analysis. The mixture was diluted with water (200 mL) and ethyl acetate (100 mL), filtered through Celite (150 g), and rinsed with ethyl acetate (300 mL). The layers were separated, and the aqueous layer was extracted with ethyl acetate (3 × 200 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel (800 g) eluting with a gradient of 10 - 40% ethyl acetate in heptane to give Compound 20 (9.17 g, 24% yield) as a pale yellow oil and Compound 20-I (10.57 g, 36% yield) as a dark brown oil.

[0225] [Chemical formula] Compound 20-I (29.2 g, 100 mmol, 1 equiv) was added to a solution of 2-furylmethyl ketone 2 (22.0 g, 200 mmol, 2.0 equiv) and titanium(IV) isopropoxide (28.4 g, 100 mmol, 1 equiv) in methanol (300 mL), followed by the addition of sodium cyanoborohydride (18.9 g, 300 mmol, 3 equiv). The mixture was refluxed for 3 days. After cooling to room temperature, sodium borohydride (ca. 1.6 g) was added portionwise until no 2-furylmethyl ketone remained by TLC analysis. The mixture was diluted with water (200 mL) and ethyl acetate (100 mL), filtered through Celite (150 g), and rinsed with ethyl acetate (300 mL). The layers were separated, and the aqueous layer was extracted with ethyl acetate (3 × 20 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel (750 g) eluting with 10% ethyl acetate in heptane to give compound 20 (19 g, 49% yield) as a pale yellow oil. 1 H NMR (400 MHz, CDCl3) δ = 7.35 (dd, J = 0.9, 1.8 Hz, 1H), 7.31 (dd, J = 0.9, 1.8 Hz, 2H), 6.97 - 6.92 (m, 4H), 6.55 - 6.47 (m, 4H), 6.32 - 6.29 (m, 1H), 6.26 (dd, J = 1.8, 3.2 Hz, 2H), 6.14 - 6.10 (m, 2H), 4.58 (q, J = 6.6 Hz, 2H), 3.72 (s, 2H), 1.51 (d, J = 6.7 Hz, 6H), 1.37 (dd, J = 6.7, 17.4 Hz, 1H); 13 C NMR (100 MHz, CDCl3) δ = 157.47, 145.13, 141.42, 131.27, 129.56, 113.61, 110.10, 109.99 - 109.79 (m, 1C), 105.61, 105.04, 49.00, 48.44, 47.60, 40.13, 21.35, 20.96, 20.11; MS (ESI) m / z [M+H] + C25 H 26 Calculated value for N2O2, 387.2, Measured value, 387.2.

[0226] Example 9 Synthesis of 4,4'-methylenebis(N-(1-phenylethyl)aniline) (Compound 21)

Chemical formula

Chemical formula

[0227] Compound 21-I (35.0 g, 112 mmol, 1 equiv) was added to a solution of acetophenone (26.9 g, 224 mmol, 2.0 equiv) and titanium(IV) isopropoxide (31.8 g, 112 mmol, 1 equiv) in methanol (225 mL), followed by the addition of sodium cyanoborohydride (17.6 g, 280 mmol, 2.5 equiv). The mixture was refluxed for 3 days. After cooling to room temperature, sodium borohydride (ca. 1.7 g) was added portionwise until no acetophenone remained by TLC analysis. The mixture was diluted with water (200 mL) and ethyl acetate (200 mL), filtered through Celite (150 g), and rinsed with ethyl acetate (300 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (3 × 200 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel (800 g) eluting with 10% ethyl acetate in heptane to afford Compound 21 (22.9 g, 50% yield) as a white solid. 1 H NMR (400 MHz, CDCl3) δ = 7.37 - 7.27 (m, 8H), 7.24 - 7.18 (m, 2H), 6.95 - 6.80 (m, 4H), 4.43 (q, J = 6.7 Hz, 2H), 3.90 (br s, 2H), 3.66 (s, 2H), 1.49 (s, 3H), 1.48 (s, 3H); 13 C NMR (100 MHz, CDCl3) δ 145.53, 145.47, 130.77, 129.47, 128.67, 126.87, 125.93, 113.41, 60.47, 53.74, 40.12, 25.11, 14.29; MS (ESI) m / z [M+H] + C 29 H 30 Calculated for C, H, N2, 407.2, found 407.3.

[0228] Example 10 Synthesis of bis(2,2,4-trimethyl-1,2-dihydroquinolin-6-yl) sulfide (Compound 153) [Chemistry] A 250 mL round-bottom flask equipped with a stir bar and a reflux condenser was loaded with the substrate 4,4'-thiodianiline (25.17 g; 116.4 mmol) and acetone (34 mL; 463 mmol). The mixture was stirred under an N2 blanket. The substrate dissolved within a few minutes. The flask was cooled by a cold water bath. To the resulting dark solution, zinc(II) triflate (5.67 g; 15.6 mmol) was added portionwise over 5 - 6 minutes. The reaction mixture was stirred for 1 + 1 / 3 hours. The cooling bath was removed. The reaction mixture was stirred for approximately 16 hours without external cooling or heating. The reaction mixture was heated for approximately 8 hours (oil bath temperature = 73 °C) and then cooled to room temperature overnight. Mesityloxide (27 mL; 0.24 mol) was added to the flask. The reaction mixture was refluxed for approximately 8 hours (oil bath temperature = 85 °C) and then cooled to room temperature overnight. Ethyl acetate (50 mL) was added. The resulting mixture was filtered through a pad of Celite. The cake was rinsed with ethyl acetate (10 mL). Volatiles were removed from the combined filtrate under reduced pressure (rotary evaporator; water bath = 55 °C). The residue (a dark, sticky material) was dissolved in toluene (21 mL). The resulting solution was loaded into a 73 mm inner diameter column (silica height = 21 cm) pre-packed with silica gel 60 and 20% ethyl acetate in hexane. The column was eluted with 20% ethyl acetate in hexane. Each fraction eluted was analyzed by silica gel TLC (20% ethyl acetate in hexane). R f Fractions containing dots with R = 0.5 were collected under reduced pressure, combined, and volatiles were removed (rotary evaporator; water bath = 50 °C). The resulting pale yellow mass (approximately 14 g) was broken into a fine powder. 10% ethyl acetate in dichloromethane mixture (35 mL) was added and the resulting slurry was stirred at room temperature for 4 hours (stir bar). The solid was collected by vacuum filtration, rinsed rapidly with multiple portions of hexane (total = 100 mL), and dried under vacuum at 40 - 50 °C for several hours and then overnight at room temperature to give 7.97 g of compound 153 (18% based on 4,4'-thiodianiline) as a white powder. Representative 1H and 13 The 1H and 13C APT NMR spectra are shown in FIGS. 4(a) and 4(b), respectively. LC-UV analysis indicated a purity of 98.2% with detection at 260 nm. The melting point of Compound 153 was measured to be approximately 184 °C.

[0229] Example 11 Synthesis of 4,4’-Methylenebis(N-isopropyl-2,6-dimethylaniline) (Compound 154)

Chemical Structure

[0230] Example 12 Use of Multiple Compounds of the Present Disclosure in Sidewall Formulations In this study, rubber compounds were prepared using multiple compounds of the present disclosure as antioxidants in sidewall formulations. As shown in Table 2, these rubber compounds are 50 / 50 blends of natural rubber and butadiene rubber with N500 series carbon black. Multiple compounds of the present disclosure or sidewall compounds without antioxidants can be seen in the examples listed in Table 2. The vulcanization characteristics of all compounds were characterized at 160 °C for 60 minutes using a Moving Die Rheometer (Alpha Technologies MDR 2000), also known as an MDR, in accordance with American Society for Testing Materials (ASTM) test method D5289. The oscillatory strain and frequency were set to 0.5 °C and 1.667 Hz, respectively. The MDR results are summarized in Table 3.

Table 2

Table 3

[0231] Example 13 Ozone Degradation Prevention Performance of Multiple Compounds of the Present Disclosure in Sidewall Compounds Each of the rubber compounds prepared in Example 12 was at its T 90It was cured at 150 °C or 160 °C until it reached a state equivalent to time. The ozone test samples were taken from the vulcanized tensile sheet by using a die according to the American Society for Testing and Materials (ASTM) D1329 standard. The ozone test samples were stored in the ambient environment for more than 24 hours before the ozone degradation prevention performance test in an ozone chamber maintained at an ozone concentration of 10 ± 2 parts per hundred million (pphm) and 40 ± 2 °C. The ozone test samples were simultaneously relaxed and expanded in the ozone chamber under three different conditions: static, intermittent, and dynamic (150 °C test), or under dynamic conditions (160 °C test). The ozone test samples were maintained at 25% strain during static exposure and alternately relaxed and expanded to 25% strain at a rate of 90 cycles per minute during dynamic exposure. The intermittent test consisted of alternating 18 minutes of dynamic exposure and 102 minutes of static exposure. The exposure was in 16-hour increments and then, after being taken out of the ozone chamber, it was relaxed for at least 1 hour before measuring the force at 100% strain.

[0232] The ozone degradation prevention performance of the compound containing the decomposition inhibitor was evaluated by the percentage of force retention. The percentage of force retention was defined by Equation 1.

[0233] [Chemical formula] In the formula, F0 is the force at 100% strain before the ozone test, and F is the force at 100% strain after the sample was aged in the ozone chamber in a 16-hour cycle of static exposure, intermittent exposure, or dynamic exposure. The higher the percentage of force retention, the better the ozone degradation prevention performance of the decomposition inhibitor compound incorporated in the vulcanized rubber compound is shown.

[0234] The forces of the aged ozone test samples and non-aged ozone test samples were measured at 100% strain by using a tensiometer (Alpha Technologies, 2000). The percentage of force retention was calculated and plotted as a function of ozone aging time in FIGS. 6(a) - 6(c) (150 °C test) and FIG. 7 (160 °C test).

[0235] Example 14 Oxidation induction time (OIT) performance of multiple compounds of the present disclosure To demonstrate the antioxidant effectiveness of multiple compounds of the present disclosure, the oxidation induction time (OIT) of selected examples was evaluated. OIT, also known as DSC, is measured according to a procedure performed on a differential scanning calorimeter (TA Instruments, Q200), which is used to predict the thermal oxidation performance of materials. In this procedure, each sample is maintained in a sample cell and heated under a nitrogen atmosphere to a preselected temperature. Then oxygen is introduced into the sample cell and the length of time before the onset of decomposition (observed by the onset of an increase in heat flow) is measured.

[0236] 0.5 wt% of one compound of the present disclosure (N 1 -(4-methylpentan-2-yl)-N 4 -phenylbenzene-1,4-diamine (6PPD)), or without a decomposer (blank), was mixed with polyisoprene and heated isothermally at 150 °C and / or 160 °C in O2. The peak time of the OIT test in minutes is shown in Table 4. As indicated by the data in Table 4, the molecules of the present invention demonstrate some antioxidant performance compared to the blank control and show usefulness in rubbers and other applications that can benefit from an active antioxidant. [Table 4]

[0237] Example 15 Use of multiple compounds of the present disclosure in tread compounds The rubber compounds were prepared using a plurality of the disclosed compounds as antioxidants in the tread formulation. As shown in Table 5, these rubber compounds are 70 / 30 blends of styrene-butadiene rubber and butadiene rubber with silica and carbon black. In accordance with American Society for Testing Materials (ASTM) test method D5289, the vulcanization characteristics of all compounds were characterized at 160 °C for 60 minutes by a moving die rheometer (Alpha Technologies MDR 2000), also known as an MDR. The vibration strain and frequency were set to 0.5 °C and 1.667 Hz, respectively. The MDR results are summarized in Table 6.

Table 5

Table 6

[0238] Example 16 Use of a Plurality of the Disclosed Compounds in a Tread Compound Each of the rubber compounds prepared in Example 15 was cured at 160 °C to a state equivalent to the time of T90 + 2 minutes. Ozone test specimens were cut from the vulcanized tensile sheet using a die in accordance with American Society for Testing and Materials (ASTM) D1329 standard. The ozone test specimens were stored in the ambient environment for more than 24 hours before the ozone degradation prevention performance test in an ozone chamber maintained at an ozone concentration of 10 ± 2 parts per hundred million (pphm) and 40 ± 2 °C. The ozone test specimens were simultaneously relaxed and expanded in the ozone chamber under dynamic conditions. The ozone test specimens were expanded to 25% strain at a rate of 90 cycles per minute during dynamic exposure. The exposure was in 16-hour increments, followed by at least 1 hour of relaxation before measuring the force at 100% strain after removal from the ozone chamber.

[0239] The ozone degradation prevention performance of the compound containing the decomposition inhibitor was evaluated by the percentage of force retention. The percentage of force retention is defined by Equation 1 above.

[0240] The forces of the aged ozone test sample and the non-aged ozone test sample were measured at 100% strain by using a tensiometer (Alpha Technologies, 2000). The percentage of force retention was calculated and plotted as a function of ozone aging time in FIG. 8.

[0241] Although the methods, compounds, and compositions have been described fully herein, it will be understood by those skilled in the art that the same can be accomplished within the broad scope and equivalent scope of conditions, formulations, and other parameters without affecting the scope or any embodiments of the methods, compounds, and compositions provided herein. All patents, patent applications, and publications cited herein are hereby incorporated by reference in their entirety.

Claims

1. A compound having the formula (I): 【Chemical Formula 59】 or a salt or solvate thereof [wherein, R １ is selected from the group consisting of C １ -C １２ alkyl, -CHR １ａ R １ｂ , C ３ -C ６ cycloalkyl, and optionally substituted phenyl; or R １ and R ４ together with each of the nitrogen and carbon atoms to which they are attached form a saturated or partially saturated optionally substituted 5- or 6-membered heterocycle; R １ａ is selected from the group consisting of optionally substituted phenyl, C ３ -C ６ cycloalkyl, and optionally substituted 5- or 6-membered heteroaryl; R １ｂ is selected from the group consisting of hydrogen and C １ -C ６ alkyl; R ２ is selected from the group consisting of C １ -C １２ alkyl, -CHR ２ａ R ２ｂ , C ３ -C ６ cycloalkyl, and optionally substituted phenyl; or R ２ and R ８ together with each of the nitrogen and carbon atoms to which they are attached form a saturated or partially saturated optionally substituted 5- or 6-membered heterocycle; R ２ａ is selected from the group consisting of optionally substituted phenyl, C ３ -C ６ cycloalkyl, and optionally substituted 5- or 6-membered heteroaryl; R ２ｂ is selected from the group consisting of hydrogen and C １ -C ６ -alkyl; X is selected from the group consisting of -CHR ３ａ -, -NR ３ｂ -, -O-, and -S-; R ３ａ is selected from the group consisting of hydrogen, C １ -C １２ -alkyl, C ３ -C ６ -cycloalkyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heterocycle, and optionally substituted 5- or 6-membered heteroaryl; R ３ｂ is selected from the group consisting of hydrogen, C １ -C １２ -alkyl, C ３ -C ６ -cycloalkyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heterocycle, and optionally substituted 5- or 6-membered heteroaryl; R ４ , R ５ , R ６ , and R ７ are independently selected from the group consisting of hydrogen, halogen, C １ -C ６ -alkyl, C １ -C ６ -alkoxy, and C １ -C ６ -alkylthio; or R １ and R ４ together with the nitrogen and carbon atoms to which they are attached form a saturated or partially saturated optionally substituted 5- or 6-membered heterocycle; R ５ , R ６ , and R ７ are selected from the group consisting of hydrogen, halogen, C １ -C ６ -alkyl, C １ -C ６ -alkoxy, and C １ -C ６ independently selected from the group consisting of alkylthio; R ８ , R ９ , R １０ , and R １１ is hydrogen, halogen, C １ -C ６ alkyl, C １ -C ６ alkoxy, and C １ -C ６ alkylthio, independently selected from the group consisting thereof; or R ２ and R ８ together with the nitrogen and carbon atoms to which they are attached form a saturated or partially saturated optionally substituted 5- or 6-membered heterocycle; R ９ , R １０ , and R １１ is hydrogen, halogen, C １ -C ６ alkyl, C １ -C ６ alkoxy, and C １ -C ６ alkylthio, independently selected from the group consisting thereof].

2. The compound according to claim 1, or a salt or solvate thereof, wherein X is -NR ３ｂ -.

3. The compound according to claim 1, or a salt or solvate thereof, wherein X is -O-.

4. The compound according to claim 1, or a salt or solvate thereof, wherein X is -S-.

5. The compound according to claim 1, or a salt or solvate thereof, wherein X is -CHR ３ａ -.

6. The compound according to claim 5 having formula (II): 【Chemical Formula 60】 or a salt or solvate thereof [wherein R ３ａ is C １ -C １２ alkyl, C ３ -C ６ cycloalkyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl, selected from the group consisting of, provided that, [Chemical Formula 61] are not equal].

7. The compound according to claim 5 having the formula (III): [Chemical Formula 62] or a salt or solvate thereof [wherein, R ３ａ is C １ -C １２ alkyl, C ３ -C ６ cycloalkyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl, selected from the group consisting of, provided that, [Chemical Formula 63] are not equal].

8. R １ and R ２ are independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, and optionally substituted phenyl, the compound according to any one of claims 1 to 7 or a salt or solvate thereof.

9. R １ and R ２ are isopropyl, the compound according to claim 8 or a salt or solvate thereof.

10. R ４ 、R ５ 、R ６ 、R ７ 、R ８ 、R ９ 、R １０ 、and R １１ The compound, salt or solvate according to any one of claims 1 to 9, wherein R is selected from the group consisting of hydrogen and methyl.

11. R ４ 、R ５ 、R ６ 、R ７ 、R ８ 、R ９ 、R １０ 、and R １１ are hydrogen, the compound, salt or solvate according to claim 10.

12. The compound, salt or solvate according to any one of claims 1 or 5 to 11, wherein R ３ａ is selected from the group consisting of 【Chemical Formula 64】 ; and Q is -NH-, -O-, or -S-.

13. R ３ａ is C １ -C １２ alkyl, the compound, salt or solvate according to claim 12.

14. R ３ａ is methyl, ethyl, propyl, isopropyl, butyl, iso-butyl, sec-butyl, or tert-butyl, the compound, salt or solvate according to claim 13.

15. R ３ａ is 【Chemical Formula 65】 the compound, salt or solvate according to claim 12.

16. Q is -O-, the compound, salt or solvate according to claim 15.

17. The compound, salt or solvate according to claim 5 having the formula (IV): 【Chemical Formula 66】 or a salt or solvate thereof [wherein, each 【Chemical formula 67】 is a single bond or a double bond; R １ｃ 、R １ｄ 、R １ｅ 、R ２ｃ 、R ２ｄ 、and R ２ｅ are independently selected from the group consisting of hydrogen and C １ -C ６ alkyl].

18. The compound according to claim 5 having the formula (IVa) or a salt or solvate thereof: 【Chemical formula 68】 or a salt or solvate thereof [wherein, each 【Chemical formula 69】 is a single bond or a double bond; R １ｃ 、R １ｄ 、R １ｅ 、R ２ｃ 、R ２ｄ 、and R ２ｅ are independently selected from the group consisting of hydrogen, C １ -C ９ alkyl, C ３ -C ６ cycloalkyl, and optionally substituted phenyl; R １ｆ and R ２ｆ are hydrogen, halogen, C １ -C ９ alkyl, C １ -C ９ haloalkyl, C ３ -C ８ cycloalkyl, -OH, -SH, C １ -C ８ alkoxy, C １ -C ８Independently selected from the group consisting of alkylthio, arylthio, -C(=O)OR, -OC(=O)R, -C(=O)NRR', -NRC(=O)R', -NRR', -SC(=O)R, -SC(=O)SR, -SC(=O)NRR', -NRC(=O)SR', -NRC(=S)SR', 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl; R and R', in each occurrence, are hydrogen, C １ -C ９ alkyl, C ３ -C ６ cycloalkyl, and optionally substituted phenyl, independently selected from the group consisting of; R １ｇ , R ２ｇ , R １ｉ , and R ２ｉ are hydrogen, C １ -C ９ alkyl, C ３ -C ６ cycloalkyl, and optionally substituted phenyl, independently selected from the group consisting of, provided that, if R １ｅ and R １ｉ the carbon atom to which they are attached forms a [Chemical Formula 70] double bond, then R １ｅ and R １ｉ are absent, and if R ２ｅ and R ２ｉ the carbon atom to which they are attached forms a [Chemical Formula 71] double bond, then R ２ｅ and R ２ｉ are absent].

19. The compound according to claim 17 having the formula (V), or a salt or solvate thereof: [Chemical Formula 72] or a salt or solvate thereof, provided that however, [Chemical Formula 73] The compound, salt or solvate thereof which is not equal.

20. The compound, salt or solvate thereof according to claim 18 having the formula (Va): 【Chemical Formula 74】 Or a salt or solvate thereof, provided that However, 【Chemical Formula 75】 The compound, salt or solvate thereof which is not equal.

21. The compound, salt or solvate thereof according to claim 17 having the formula (VI): 【Chemical Formula 76】 Or a salt or solvate thereof, provided that However, 【Chemical Formula 77】 The compound, salt or solvate thereof which is not equal.

22. The compound, salt or solvate thereof according to claim 18 having the formula (VIa): 【Chemical Formula 78】 Or a salt or solvate thereof, provided that However, 【Chemical Formula 79】 The compound, salt or solvate thereof which is not equal.

23. R ５ 、R ６ 、R ７ 、R ９ 、R １０ 、and R １１ are selected from the group consisting of hydrogen, methyl, C １ - C ６ alkoxy, and C １ - C ６ alkylthio, and the compound, salt or solvate thereof according to any one of claims 17 to 22.

24. R ５ , R ６ , R ７ , R ９ , R １０ , and R １１ is hydrogen, the compound according to claim 23 or a salt or solvate thereof.

25. R １ｃ , R １ｄ , R １ｅ , R ２ｃ , R ２ｄ , and R ２ｅ is methyl, ethyl, or hydrogen, the compound according to any one of claims 17 to 24 or a salt or solvate thereof.

26. R １ｃ , R １ｄ , R １ｅ , R ２ｃ , R ２ｄ , and R ２ｅ is methyl, the compound according to claim 25 or a salt or solvate thereof.

27. R ３ａ is hydrogen, the compound according to any one of claims 17, 18, or 23 to 26 or a salt or solvate thereof.

28. The compound according to any one of claims 17 to 26 or a salt or solvate thereof [wherein, R ３ａ is 【Chemical Formula 80】 selected from the group consisting of; Q is -NH-, -O-, or -S-].

29. R ３ａ is C １ -C １２ alkyl, the compound according to claim 28 or a salt or solvate thereof.

30. R ３ａThe compound according to claim 29, or a salt or solvate thereof, wherein R is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, or tert-butyl.

31. R ３ａ is 【Chemical Formula 81】 The compound according to claim 28, or a salt or solvate thereof, wherein it is as defined above.

32. The compound according to claim 31, or a salt or solvate thereof, wherein Q is -O-.

33. The compound according to claim 1, or a salt or solvate thereof, which is selected from any one or more of the compounds in Table 1.

34. (i) a compound according to any one of claims 1 to 33; and (ii) one or more elastomers; or (iii) one or more fillers; or (iv) one or more rubber chemicals; or (v) one or more plasticizers; or (vi) a second antioxidant; or (vii) a combination of one or more elastomers, one or more fillers, one or more rubber chemicals, one or more plasticizers, and / or a second antioxidant, A composition comprising the same.

35. The composition according to claim 34, wherein the composition comprises one or more elastomers.

36. The composition according to claim 35, wherein the composition comprises about 15 wt / wt% to about 85 wt / wt% of the compound and about 15 wt / wt% to about 85 wt / wt% of the one or more elastomers.

37. The composition according to any one of claims 34 to 37, wherein the one or more elastomers comprise natural rubber (NR).

38. The composition according to claim 37, wherein the one or more elastomers comprise from about 5 wt / wt% to about 80 wt / wt% natural rubber (NR).

39. The composition according to claim 37 or 38, wherein the natural rubber comprises rubber derived from alternative rubber plants.

40. The composition according to claim 39, wherein the alternative rubber plant is Parthenium argentatum (guayule) or Taraxacum kok-saghyz (Russian dandelion).

41. The composition according to any one of claims 35 to 40, wherein the one or more elastomers comprise synthetic rubber.

42. The composition according to claim 41, wherein the synthetic rubber comprises unsaturated rubber, saturated rubber, rubber having a substituent of fluoro, fluoroalkyl, or fluoroalkoxy on the polymer chain (FKM), silicone rubber (Q), or a blend thereof.

43. The composition according to claim 42, wherein the unsaturated rubber comprises isoprene rubber (IR), butyl rubber (IIR), butadiene rubber (BR), styrene-butadiene rubber (SBR), nitrile-butadiene rubber (NBR), chloroprene rubber (CR), ethylene-propylene-diene rubber (EPDM), or a blend thereof.

44. The composition according to claim 43, wherein the unsaturated rubber comprises styrene-butadiene rubber (SBR).

45. The composition according to claim 44, wherein the one or more elastomers comprise from about 5 wt / wt% to about 80 wt / wt% styrene-butadiene rubber (SBR).

46. The composition according to any one of claims 43 to 45, wherein the unsaturated rubber contains butadiene rubber (BR).

47. The composition according to claim 46, wherein the one or more elastomers contain from about 5 wt / wt% to about 80 wt / wt% of butadiene rubber (BR).

48. The composition according to any one of claims 43 to 47, wherein the unsaturated rubber contains butyl rubber (IIR).

49. The composition according to claim 48, wherein the one or more elastomers contain from about 1 wt / wt% to about 30 wt / wt% of butyl rubber (IIR).

50. The composition according to any one of claims 42 to 49, wherein the saturated rubber contains 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.

51. The composition according to any one of claims 34 to 50, wherein the one or more elastomers further contain recycled rubber.

52. The composition according to any one of claims 34 to 51, wherein the composition contains from about 0.1 phr to about 10 phr of a compound.

53. The composition according to claim 52, wherein the composition contains from about 0.5 phr to about 5 phr of a compound.

54. The compound according to claim 53, wherein the composition contains from about 1 phr to about 5 phr of a compound.

55. The composition according to any one of claims 34 to 54, wherein the composition contains one or more fillers.

56. The composition according to claim 55, wherein the composition comprises from about 15 wt / wt% to about 85 wt / wt% of the compound and from about 15 wt / wt% to about 85 wt / wt% of the one or more fillers.

57. The composition according to claim 55 or 56, wherein the composition comprises from about 30 phr to about 500 phr of one or more fillers.

58. The composition according to any one of claims 55 to 57, wherein the one or more fillers comprise carbon black, silica, kaolin, calcium silicate, talc, carbon nanotubes (CNT), carbon fibers (HCF), graphite, graphene, aluminosilicate, starch, fiber, or combinations thereof.

59. The composition according to claim 58, wherein the one or more fillers comprise silica.

60. The composition according to claim 59, wherein the silica is derived from rice husk.

61. The composition according to any one of claims 54 to 60, wherein the one or more fillers comprise carbon black.

62. The composition according to any one of claims 34 to 61, wherein the composition comprises one or more rubber chemicals.

63. The composition according to claim 62, wherein the composition comprises from about 15 wt / wt% to about 85 wt / wt% of the compound and from about 15 wt / wt% to about 85 wt / wt% of one or more rubber chemicals.

64. The composition according to claim 62 or 63, wherein the composition comprises from about 0.1 phr to about 30 phr of one or more rubber chemicals.

65. The composition according to claim 64, wherein the composition comprises from about 1 phr to about 20 phr of one or more rubber chemicals.

66. The composition according to any one of claims 62 to 65, wherein the one or more rubber chemicals comprise one or more vulcanizing agents, one or more accelerators, one or more activators, one or more scorch inhibitors, or combinations thereof.

67. The composition according to claim 66, wherein the one or more rubber chemicals comprise one or more vulcanizing agents.

68. The composition according to claim 67, wherein the one or more vulcanizing agents comprise sulfur, peroxide, resin, or combinations thereof.

69. The sulfur is octasulfur (S ８ ), cyclododecasulfur (S １２ ), polymeric sulfur, or combinations thereof, in the composition according to claim 68.

70. The peroxide comprises benzoyl peroxide, dicumyl peroxide (DC), 2,5-dimethyl-2,5-di-(tert-butylperoxy)-3-hexyne (2,5Tri), 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 combinations thereof, in the composition according to claim 68.

71. The resin is an adhesive resin, in the composition according to claim 68.

72. The composition according to any one of claims 66 to 71, wherein the one or more rubber chemicals comprise one or more accelerators.

73. The composition according to claim 72, wherein the one or more accelerators comprise guanidine, thiazole, sulfenamide, thiuram, dithiocarbamate, xanthate, thiophosphate, or combinations thereof.

74. The composition according to claim 73, wherein the guanidine is diphenylguanidine (DPG).

75. The composition according to claim 73, wherein the thiazole comprises 2-mercaptobenzothiazole (MBT), zinc 2-mercaptobenzothiazole (ZMBT), mercaptobenzothiazole disulfide (MBTS), N-tert-butyl-2-benzothiazolesulfenimide (TBTS), or a combination thereof.

76. Non-limiting examples of sulfenamides include N-tert-butyl-2-benzothiazylsulfenamide (TBBS), N-cyclohexylbenzothiazole-2-sulfenamide (CBS), dicyclohexyl-2-benzothiazolesulfenamide (DCBS), N-oxydiethylene benzothiazole sulfenamide (OBTS), N-oxydiethylene thiocarbamyl-N'-oxydiethylene sulfenamide (OTOS), thiocarbamyl sulfenamide, or a combination thereof. The composition according to claim 73.

77. The composition according to claim 73, wherein the thiuram comprises dimethylcarbamothioic dithio peroxide (thiuram), dipentamethylene thiuram tetrasulfide (DPIT), tetrabenzylthiuram disulfide (TBzTD), tetraethylthiuram disulfide (TETD), tetramethylthiuram disulfide (TMTD), tetramethylthiuram sulfide (TMTM), or a combination thereof.

78. The composition according to claim 73, wherein the dithiocarbamate comprises zinc dimethyldithiocarbamate (ZDMC), zinc diethyldithiocarbamate (ZDBC), zinc dibutyldithiocarbamate (ZDBC), nickel dibutyldithiocarbamate (NDBC), sodium dibenzyldithiocarbamate (SBEC), sodium diethyldithiocarbamate (SDEC), tellurium diethyldithiocarbamate (TDEC), zinc dibenzyldithiocarbamate (ZEBC), or a combination thereof.

79. The composition according to any one of claims 66 to 78, wherein the one or more rubber chemicals comprise one or more activators.

80. The composition according to claim 79, wherein the one or more activators comprise a metal oxide, an acid, a metal complex, or a combination thereof.

81. The composition according to claim 80, wherein the metal oxide comprises zinc oxide, magnesium oxide, lead oxide, or a combination thereof.

82. The composition according to claim 80, wherein the acid comprises stearic acid, lauric acid, or a combination thereof.

83. The composition according to claim 80, wherein the metal complex comprises zinc ethylhexanoate.

84. The composition according to any one of claims 66 to 83, wherein the one or more rubber chemicals comprise one or more scorch inhibitors.

85. The composition according to claim 84, wherein the one or more scorch inhibitors comprise N-(cyclohexylthio)phthalimide (CTP), benzoic anhydride, salicylic anhydride, phthalic anhydride, or a combination thereof.

86. The composition according to any one of claims 34 to 85, wherein the composition comprises one or more plasticizers.

87. The composition according to claim 86, wherein the composition comprises from about 15 wt / wt% to about 85 wt / wt% of the compound and from about 15 wt / wt% to about 85 wt / wt% of one or more plasticizers.

88. The composition according to claim 86 or 87, wherein the composition comprises from about 0.1 phr to about 30 phr of one or more plasticizers.

89. The composition according to claim 88, wherein the composition comprises from about 1 phr to about 20 phr of one or more plasticizers.

90. The composition according to any one of claims 86 to 89, wherein the one or more plasticizers comprise mineral oil, organic ester, resin, wax, ester plasticizer, oil of natural origin, or a combination thereof.

91. The composition according to claim 90, wherein the mineral oil is naphthenic oil, paraffinic oil, or aromatic oil.

92. The composition according to claim 90, wherein the oil of natural origin is soybean oil, vegetable oil, or orange oil.

93. The composition according to any one of claims 34 to 92, wherein the composition further comprises a second antioxidant.

94. The composition according to claim 93, wherein the composition comprises from about 15 wt / wt% to about 85 wt / wt% of the compound and from about 15 wt / wt% to about 85 wt / wt% of the second antioxidant.

95. The composition according to claim 93 or 94, wherein the second antioxidant is present in an amount of from about 0.001 phr to about 10 phr.

96. The composition according to claim 95, wherein the second antioxidant is present in an amount of from about 0.1 phr to about 5 phr.

97. The composition according to claim 96, wherein the second antioxidant is present in an amount of from about 0.5 phr to about 5 phr.

98. The composition according to claim 97, wherein the second anti-degradant is present in an amount of about 1 phr to about 5 phr.

99. The composition according to any one of claims 93 to 98, wherein the second anti-degradant is an antioxidant.

100. The composition according to any one of claims 93 to 98, wherein the second anti-degradant is an anti-ozone degradation agent.

101. The composition according to any one of claims 93 to 100, wherein the second anti-degradant is paraphenylenediamine (PPD), trimethyldihydroquinoline (TMQ), phenols, alkylated diphenylamine (DPA), or diphenylamine-ketone condensate.

102. 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 -(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), or N-N'-dioctyl-p-phenylenediamine (88PD), and the composition according to claim 101.

103. The composition according to claim 102, wherein the PPD is 6PPD.

104. The composition according to claim 101, wherein the TMQ is 2,2,4-trimethyl-1,2-dihydroquinoline or an oligomer or polymer thereof.

105. A composition comprising the compound according to any one of claims 1 to 33 and one or more carriers.

106. A process for preparing the composition according to claim 105, the process comprising mixing the compound and one or more carriers.

107. A vulcanized elastomer article comprising the compound according to any one of claims 1 to 33.

108. A vulcanized elastomer article prepared using the composition according to any one of claims 34 to 105.

109. The vulcanized elastomer article according to claim 107 or 108, wherein the vulcanized elastomer article is a tire.

110. The vulcanized elastomer article according to claim 109, 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 construction machinery tire, an aircraft tire, or a racing tire.

111. The vulcanized elastomer article according to claim 107 or 108, wherein the vulcanized elastomer article is a component of a tire.

112. The vulcanized elastomer article according to claim 111, wherein the component is a bead, a belt, a body ply, an inner liner, a sidewall, an undertread, or a tread.

113. The vulcanized elastomer article according to claim 107 or 108, wherein the vulcanized elastomer article is a rubber overshoe, a sealing strip, a sound absorbing panel, an air spring, a bellows, a membrane, a tactile sensor, a safety pad, a hose, a conveyor belt, or a flooring.

114. A process for preparing a vulcanized elastomer article, (a) forming the composition according to any one of claims 33 to 105 into a shaped form; (b) vulcanizing the shaped form to provide a vulcanized elastomer article, and the process comprising the same. **Claim 115** The process according to claim 114, wherein the vulcanization is carried out at an average temperature of about 120 °C to about 180 °C. **Claim 116** The process according to claim 115, wherein the vulcanization is carried out at an average temperature of about 140 °C to about 160 °C. **Claim 117** The process according to any one of claims 114 to 116, wherein the vulcanized elastomer article is a tire. **Claim 118** The process according to claim 117, 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 construction machinery tire, an aircraft tire, or a racing tire. **Claim 119** The process according to any one of claims 114 to 118, wherein the vulcanized elastomer article is a component of a tire. **Claim 120** The process according to claim 119, wherein the component is a bead, a belt, a body ply, an inner liner, a sidewall, an undertread, or a tread. **Claim 121** The process according to any one of claims 114 to 116, wherein the vulcanized elastomer article is a rubber overshoe, a sealing strip, a sound absorbing panel, an air spring, a bellows, a membrane, a tactile sensor, a safety pad, a hose, a conveyor belt, or a flooring. **Claim 122** A lubricant composition comprising a lubricant and a compound according to any one of claims 1 to 33. **Claim 123** A combustible fuel composition comprising a combustible fuel and a compound according to any one of claims 1 to 33.

124. A fuel additive composition comprising a fuel additive and a compound according to any one of claims 1 to 33.

125. A process for retreading a tire, comprising: (a) applying a composition according to any one of claims 34 to 105 to the tire; (b) disposing a pre-cured tread around the tire; (c) disposing a curing envelope around the tire; (d) vulcanizing the tire. The process as described above.

126. A kit comprising a composition according to any one of claims 34 to 105 and instructions for using the composition in a vulcanizable elastomer composition.

127. A kit comprising a composition according to any one of claims 34 to 105 and instructions for preparing a vulcanized elastomer article using the composition.

128. The composition according to claim 34, wherein the composition comprises from about 0.1 wt / wt% to about 10 wt / wt% of the compound.

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