Anti-degradation compounds and uses thereof

Abstract

The present disclosure provides a compound represented by formula (I), or a salt or solvate thereof, wherein R1, R2, R4, R5, R6, R7, R8, R9, R10, R11 and X are as defined in the specification. The present disclosure also provides compositions, vulcanized elastomeric articles, lubricant compositions, combustible fuel compositions, and fuel additive compositions comprising the compounds disclosed herein. The present disclosure also provides methods of making the compositions and vulcanized elastomeric articles described herein. The present disclosure also provides methods of retreading a tire using the compositions described herein. The present disclosure also provides kits comprising the compositions described herein. # imgabs0 #

Description

Background Art Technical Field

[0001] The present disclosure provides compounds having anti-degradation (e.g., anti-ozone, anti-oxidation and / or anti-fatigue) properties that are useful additives for vulcanized rubber articles, compositions containing elastomers, lubricants, fuels, and other compositions requiring such properties, or that can themselves serve as compositions that impart such properties.

[0003] Many materials such as plastics, elastomers, elastomeric products (tires, belts, hoses, bushings, brackets, vibration isolators, etc.), lubricants and petroleum products (such as hydraulic fluids, oils, fuels and oil / fuel additives for automotive and aviation applications) are susceptible to degradation when exposed to light, heat, oxygen, ozone, repetitive mechanical action, etc. for a long time. Therefore, compounds and compositions that exhibit anti-degradation efficacy are well known in the art. For example, U.S. Patent No. 8,987,515 discloses an aromatic polyamine that can be used to inhibit oxidative degradation, particularly in lubricant compositions. U.S. Patent Application Publication No. 2014 / 0316163 discloses antioxidant macromolecules that are said to have improved solubility in many commercially available oils and lubricants.

[0004] Antidegradants for making products formed from elastomers, plastics, etc. require a very specific combination of qualities, which may be difficult to achieve. Although antidegradants must obviously have commercially acceptable efficacy, they must also exhibit this efficacy over a long period of time associated with the use of the product, particularly on the exposed surface of the product, because degradation caused by environmental factors (such as light, oxygen, and ozone) primarily occurs on the surface. Equally important as protecting surface exposed parts, the efficacy of protecting embedded parts of composite materials from the effects of oxidative aging and repeated mechanical action is crucial. Antidegradants must achieve these results without negatively affecting the efficacy of other additives or the desired properties of the final product. In addition, antidegradants that provide or improve the mechanical fatigue life of the product after use, oxidative aging, or exposure to ozone are highly valued because these will inherently improve the useful mechanical service life of the product. Therefore, elastomeric products that are subjected to repeated mechanical bending, stretching, or compression during use will greatly benefit from this discovery.

[0005] Articles formed from general purpose elastomers, such as natural rubber, and particularly tires, are particularly susceptible to degradation from oxygen and ozone. As described in U.S. Pat. No. 2,905,654, oxygen degradation affects rubber differently than ozone degradation; however, both effects can be detrimental to the performance, appearance, and life expectancy of the tire. Fatigue and crack growth are also issues of particular concern, particularly in the steel belt edge areas and tire sidewalls, which are subject to significant stress and tensile forces when the tire is inflated, partially inflated, and flexed throughout its service life. U.S. Pat. No. 8,833,417 describes an antioxidant system that is said to provide improved long-term fatigue and crack growth resistance over the known antioxidants discussed immediately below.

[0006] Materials with anti-degradation properties are well known in the field of tire applications and are commercially available. For example, N,N'-disubstituted p-phenylenediamines (such as those sold under the trademark Those sold as EP3147321A1 are generally favored by many tire manufacturers for this purpose. EP 3147321A1 discloses a rubber composition, a tire, an amine compound and an anti-aging agent, in particular a rubber composition said to be suitable for a tread rubber or a sidewall rubber of a tire. Summary of the invention

[0007] The present disclosure provides compounds useful as antidegradants (e.g., antiozonants and / or antioxidants) and / or as additives in lubricants or combustible fuels, represented by any of the following Formulas I-VI, (IVa), (Va) or (VIa), collectively referred to herein as "compounds of the present disclosure" or individually as "compounds of the present disclosure."

[0008] The present disclosure also provides a composition comprising:

[0009] (i) a compound of the present disclosure; and

[0010] (ii) one or more elastomers; or

[0011] (iii) one or more fillers; or

[0012] (iv) one or more rubber chemicals; or

[0013] (v) one or more plasticizers; or

[0014] (vi) a second antidegradant; or

[0015] (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 antidegradant, collectively referred to herein or individually as a "composition of the present disclosure."

[0016] The present disclosure also provides compositions of the present disclosure, comprising a compound of the present disclosure and one or more elastomers.

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

[0018] The present disclosure also provides a composition of the present disclosure, which comprises a compound of the present disclosure and one or more rubber chemicals.

[0019] The present disclosure also provides compositions of the present disclosure, which include a compound of the present disclosure and one or more plasticizers.

[0020] The present disclosure also provides a composition of the present disclosure, which comprises a compound of the present disclosure and a second antidegradant.

[0021] The present disclosure also provides compositions of the present disclosure, which include a compound of the present disclosure and one or more carriers.

[0022] The present disclosure also provides a method for preparing a composition comprising a compound of the present disclosure and one or more carriers, the method comprising mixing the compound with the one or more carriers.

[0023] The present disclosure also provides vulcanized elastomeric articles comprising the compounds of the present disclosure.

[0024] The present disclosure also provides vulcanized elastomeric articles prepared using the compositions described herein, such as compositions of the present disclosure or compositions comprising a compound of the present disclosure and one or more carriers.

[0025] The present disclosure also provides a method for preparing the vulcanized elastomeric article described herein, the method comprising:

[0026] (a) forming a composition as described herein into a shaped shape; and

[0027] (b) vulcanizing the formed shape,

[0028] To provide a vulcanized elastomeric product.

[0029] The present disclosure also provides a lubricant composition comprising a lubricant and a compound of the present disclosure.

[0030] The present disclosure also provides a combustible fuel composition comprising a combustible fuel and a compound of the present disclosure.

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

[0032] The present disclosure also provides a method for retreading a tire, the method comprising:

[0033] (a) applying a composition as described herein to a tire;

[0034] (b) providing a pre-cured tread around the tire;

[0035] (c) providing a curing envelope around the tire; and

[0036] (d) vulcanizing the tire.

[0037] The present disclosure also provides kits comprising the compositions described herein and instructions for using the compositions in vulcanizable elastomeric compositions.

[0038] The present disclosure also provides kits comprising the compositions described herein and instructions for using the compositions to prepare vulcanized elastomeric articles.

[0039] Other embodiments and advantages of the present disclosure will be explained in part in the following description and will be revealed from the description, or can be learned through the practice of the present disclosure. The embodiments and advantages of the present disclosure will be realized and achieved by means of the elements and combinations particularly pointed out in the appended claims.

[0040] 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

[0041] FIG1(a) is a graph depicting compound 1 in d6-dimethyl sulfoxide (d6-DMSO). 1 Line graph of the H nuclear magnetic resonance (NMR) spectrum.

[0042] Figure 1(b) depicts the structure of compound 1 in d6-DMSO. 13 Line graph of C NMR spectrum.

[0043] Figure 2(a) is a graph depicting compound 2 in d-chloroform (CDCl3). 1 Line graph of the H NMR spectrum.

[0044] Figure 2(b) shows the structure of compound 2 in CDCl3. 13 Line graph of C NMR spectrum.

[0045] Figure 3(a) depicts the structure of compound 3 in d6-DMSO. 1 Line graph of the H NMR spectrum.

[0046] Figure 3(b) depicts the structure of compound 3 in d6-DMSO. 13 Line graph of C NMR spectrum.

[0047] FIG4( a ) is a graph depicting compound 153 in d6-DMSO.1 Line graph of the H NMR spectrum.

[0048] Figure 4(b) depicts the structure of compound 153 in d6-DMSO. 13 Line graph of C NMR spectrum.

[0049] Figure 5(a) shows the structure of compound 154 in CDCl3. 1 Line graph of the H NMR spectrum.

[0050] Figure 5(b) is a graph depicting compound 154 in d8-tetrahydrofuran. 13 Line graph of C NMR spectrum.

[0051] 6(a)-(c) are line graphs showing force retention over time for sidewall compounds comprising Compound 1, 2, or 3 under (a) static, (b) intermittent, and (c) dynamic conditions.

[0052] Figure 7 is a line graph showing force retention over time for sidewall compounds comprising compounds of the present disclosure under dynamic conditions.

[0053] Figure 8 is a line graph showing force retention over time for tread compounds including the compounds of the present disclosure under dynamic conditions. DETAILED DESCRIPTION

[0054] In one embodiment, the compound of the present disclosure is a compound having formula (I):

[0055]

[0056] or a salt or solvate thereof, wherein:

[0057] R 1 Selected from the group consisting of: C1-C12 alkyl, -CHR 1a R 1b , C3-C6 cycloalkyl, and optionally substituted phenyl; or

[0058] R 1 and R 4 Together with the nitrogen atom and the carbon atom to which they are attached, they form a saturated or partially saturated optionally substituted 5- or 6-membered heterocyclic ring;

[0059] R 1a Selected from the group consisting of optionally substituted phenyl, C3-C6 cycloalkyl and optionally substituted 5 or 6 membered heteroaryl;

[0060] R 1b Selected from the group consisting of hydrogen and C1-C6 alkyl;

[0061] R 2 Selected from the group consisting of: C1-C 12 Alkyl, -CHR 2a R 2b , C3-C6 cycloalkyl, and optionally substituted phenyl; or

[0062] R 2 and R 8 Together with the nitrogen atom and the carbon atom to which they are attached, they form a saturated or partially saturated optionally substituted 5- or 6-membered heterocyclic ring;

[0063] R 2a Selected from the group consisting of optionally substituted phenyl, C3-C6 cycloalkyl and optionally substituted 5 or 6 membered heteroaryl;

[0064] R 2b Selected from the group consisting of hydrogen and C1-C6 alkyl;

[0065] X-Select Free-CHR 3a -、-NR 3b -, -O-, and -S-;

[0066] R 3a Selected from the group consisting of: 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;

[0067] R 3b Selected from the group consisting of: 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;

[0068] R 4 , R 5 , R 6 and R 7 independently selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy and C1-C6 alkylthio; or

[0069] R 1 and R 4 Together with the nitrogen atom and the carbon atom to which they are attached, they form a saturated or partially saturated optionally substituted 5- or 6-membered heterocyclic ring; and

[0070] 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; and

[0071] R 8 , R 9 , R 10 and R 11 independently selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy and C1-C6 alkylthio; or

[0072] R 2 and R 8 Together with the nitrogen atom and the carbon atom to which they are attached, they form a saturated or partially saturated optionally substituted 5- or 6-membered heterocyclic ring; and

[0073] R 9 , R 10 and R 11 Independently selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy and C1-C6 alkylthio.

[0074] In some embodiments, the compounds of the present disclosure are compounds having formula (I), wherein X is -NR 3b -.

[0075] In some embodiments, the compound of the present disclosure is a compound having formula (I), wherein X is -O-.

[0076] In some embodiments, the compounds of the present disclosure are compounds having formula (I), wherein X is -O- and R 1 and R 2 Independently selected from the group consisting of: -CHR 1a R 1b , C3-C6 cycloalkyl, and optionally substituted phenyl.

[0077] In some embodiments, the compound of the present disclosure is a compound having formula (I), wherein X is -S-.

[0078] In some embodiments, the compounds of the present disclosure are compounds having formula (I), wherein X is -S- and R 1 and R 2 Independently selected from the group consisting of: -CHR 1a R 1b , C3-C6 cycloalkyl, and optionally substituted phenyl.

[0079] In some embodiments, the compounds of the present disclosure are compounds having formula (I), wherein X is -CHR 3a -.

[0080] In some embodiments, the compounds of the present disclosure are compounds having formula (I), wherein if X is -CH2-, then:

[0081] (i)R1 Selected from the group consisting of: nonyl, decyl, undecyl, dodecyl, -CHR 1a R 1b and C3-C5 cycloalkyl; or

[0082] (ii) R 1 and R 4 Together with the nitrogen atom and the carbon atom to which they are attached, they form a saturated or partially saturated optionally substituted 5- or 6-membered heterocyclic ring;

[0083] R 1a Selected from the group consisting of substituted phenyl, C3-C6 cycloalkyl and optionally substituted 5 or 6 membered heteroaryl;

[0084] R 1b Selected from the group consisting of hydrogen and C1-C6 alkyl;

[0085] R 2 Selected from the group consisting of: nonyl, decyl, undecyl, dodecyl, -CHR 2a R 2b and C3-C5 cycloalkyl; or

[0086] (iii) R 2 and R 8 Together with the nitrogen atom and the carbon atom to which they are attached, they form a saturated or partially saturated optionally substituted 5- or 6-membered heterocyclic ring;

[0087] R 2a is selected from the group consisting of substituted phenyl, C3-C6 cycloalkyl, and optionally substituted 5- or 6-membered heteroaryl; and

[0088] R 2b Selected from the group consisting of hydrogen and C1-C6 alkyl.

[0089] In some embodiments, the compounds of the present disclosure are compounds having formula (I), wherein if X is -CHCH3-, then:

[0090] (i)R 1 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

[0091] (ii) R 1 and R 4 Together with the nitrogen atom and the carbon atom to which they are attached, they form a saturated or partially saturated optionally substituted 5- or 6-membered heterocyclic ring; and

[0092] R 2 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

[0093] (iii) R 2 and R 8 Together with the nitrogen atom and the carbon atom to which they are attached, they respectively form a saturated or partially saturated optionally substituted 5- or 6-membered heterocyclic ring.

[0094] In some embodiments, the compounds of the present disclosure are compounds having formula (I), wherein if X is -O-, then:

[0095] (i)R 1 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

[0096] (ii) R 1 and R 4 Together with the nitrogen atom and the carbon atom to which they are attached, they form a saturated or partially saturated optionally substituted 5- or 6-membered heterocyclic ring; and

[0097] R 2 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

[0098] (iii) R 2 and R 8 Together with the nitrogen atom and the carbon atom to which they are attached, they respectively form a saturated or partially saturated optionally substituted 5- or 6-membered heterocyclic ring.

[0099] In some embodiments, the compounds of the present disclosure are compounds having Formula (I), wherein if X is -S-, then:

[0100] (i)R 1 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

[0101] (ii) R 1 and R 4 Together with the nitrogen atom and the carbon atom to which they are attached, they form a saturated or partially saturated optionally substituted 5- or 6-membered heterocyclic ring; and

[0102] R 2 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

[0103] (iii) R 2 and R 8 Together with the nitrogen atom and the carbon atom to which they are attached, they respectively form a saturated or partially saturated optionally substituted 5- or 6-membered heterocyclic ring.

[0104] In some embodiments, the compounds of the present disclosure are compounds having formula (I), wherein if X is -CH2-, then R 1 and R 2 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-((oct-2-yl)amino)phenyl or 4-(cyclohexylamino)phenyl.

[0105] In some embodiments, the compounds of the present disclosure are compounds having formula (I), wherein if X is -C(CH3)2-, then R 1 and R 2 Not sec-butyl.

[0106] In some embodiments, the compounds of the present disclosure are compounds having formula (I), wherein if X is -CH2-, R 1 and R 2 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.

[0107] In some embodiments, the compounds of the present disclosure are compounds having formula (I), wherein if X is -CH2-, then R 1 and R2 Not methyl, ethyl, propyl, isopropyl or butyl.

[0108] In some embodiments, the compounds of the present disclosure are compounds of formula (I), wherein if X is -CH2- and R 5 and R 9 is methyl, then R 1 and R 2 Not sec-butyl.

[0109] In some embodiments, the compounds of the present disclosure are compounds of formula (I), wherein if X is -CH2- and R 4 and R 8 is methyl, then R 1 and R 2 Not isopropyl or sec-butyl.

[0110] In some embodiments, the compounds of the present disclosure are compounds having formula (I), wherein if X is -O-, then R 1 and R 2 Not isopropyl or sec-butyl.

[0111] In some embodiments, the compounds of the present disclosure are compounds having formula (I), wherein if X is -S-, then R 1 and R 2 Not isopropyl, sec-butyl or -CH(CH3)(CH2)5CH3.

[0112] In another embodiment, the compound of the present disclosure is a compound having formula (II):

[0113]

[0114] or a salt or solvate thereof, wherein R 3a Selected from the group consisting of: C1-C 12 alkyl, C3-C6 cycloalkyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl; and R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 As defined for formula (I),

[0115] The condition is Not equivalent to

[0116] In another embodiment, the compound of the present disclosure is a compound having formula (III):

[0117]

[0118] or a salt or solvate thereof, wherein R 3a is selected from the group consisting of C1-C12 alkyl, C3-C6 cycloalkyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl; and R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 As defined for formula (I),

[0119] The condition is Not equivalent to

[0120] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(III), wherein R 1 and R 2 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.

[0121] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(III), wherein R 1 and R 2 It is isopropyl.

[0122] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(III), wherein R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 is selected from the group consisting of hydrogen and methyl.

[0123] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(III), wherein R 4 , R 5 , R 6 , R 7 , R 8 , R9 , R 10 and R 11 It's hydrogen.

[0124] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(III), wherein X is -CHR 3a ; R 3a Selected from the group consisting of: C1-C 12 alkyl,

[0125]

[0126] and Q is -NH-, -O- or -S-.

[0127] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(III), wherein X is -CHR 3a And R 3a It is C1-C 12 alkyl.

[0128] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(III), wherein X is -CHR 3a And R 3a It is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl.

[0129] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(III), wherein X is -CHR 3a And R 3a 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.

[0130] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(III), wherein X is -CHR 3a And R 3a It is a C3-C6 cycloalkyl group.

[0131] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(III), wherein X is -CHR 3a And R 3a is optionally substituted phenyl.

[0132] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(III), wherein X is -CHR 3a And R 3a is an optionally substituted 5- or 6-membered heterocyclic ring.

[0133] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(III), wherein X is -CHR 3a And R 3a is an optionally substituted 5- or 6-membered heteroaryl.

[0134] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(III), wherein X is -CHR 3a And R 3a yes:

[0135]

[0136] In some embodiments, the compound of the present disclosure is a compound of any one of Formula (I)-(III), wherein Q is -O-.

[0137] In another embodiment, the compound of the present disclosure is a compound having formula (IV):

[0138]

[0139] or a salt or solvate thereof, wherein:

[0140] Each is a single bond or a double bond;

[0141] R 1c , R 1d , R 1e , R 2c , R 2d and R 2e are independently selected from the group consisting of hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl; and

[0142] R 5 , R 6 , R 7 , R 9 , R 10 and R 11 As defined for formula (I).

[0143] In some embodiments, the compounds of the present disclosure are 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. 1c , R 1e , R 2c and R 2eIn some embodiments, R 1c , R 1e , R 2c and R 2e It is ethyl.

[0144] In another embodiment, the compound of the present disclosure is a compound having formula (IVa):

[0145]

[0146] or a salt or solvate thereof, wherein:

[0147] Each is a single bond or a double bond;

[0148] R 1f and R 2f 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;

[0149] R and R' at each occurrence are independently selected from the group consisting of hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl;

[0150] R 1g , R 2g , R 1i and R 2i independently selected from the group consisting of hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl and optionally substituted phenyl, provided that if attached to R 1e and R 1i Connected Carbon is a double bond, then R 1e and R 1i does not exist, and if connected with R 2e and R 2i Connected Carbon is a double bond, then R 2e and R 2i does not exist;

[0151] R 5 , R 6 , R 7 , R 9 , R10 and R 11 As defined with respect to formula (I); and

[0152] R 1c , R 1d , R 1e , R 2c , R 2d and R 2e As defined for formula (IV).

[0153] In some embodiments, the compound of the present disclosure is a compound of formula (IVa), wherein It is a single bond.

[0154] In some embodiments, the compound of the present disclosure is a compound of formula (IVa), wherein is a single bond and R 1c , R 1f , R 2c and R 2f It's methyl.

[0155] In some embodiments, the compound of the present disclosure is a compound of formula (IVa), wherein is a single bond and R 1i , R 1g , R 2i and R 2g It's methyl.

[0156] In another embodiment, the compound of the present disclosure is a compound having Formula (V):

[0157]

[0158] or a salt or solvate thereof, wherein:

[0159] Each is a single bond or a double bond;

[0160] R 1c , R 1d , R 1e , R 2c , R 2d and R 2e are independently selected from the group consisting of hydrogen and C1-C6 alkyl; and

[0161] R 5 , R 6 , R 7 , R 9 , R 10 and R 11 As defined for formula (I),

[0162] The condition is Not equivalent to

[0163] In another embodiment, the compound of the present disclosure is a compound having Formula (Va):

[0164]

[0165] or a salt or solvate thereof, wherein:

[0166] Each is a single bond or a double bond;

[0167] The condition is that if the connection with R 1e and R 1i Connected Carbon is a double bond, then R 1e and R 1i does not exist, and if connected with R 2e and R 2i Connected Carbon is a double bond, then R 2e and R 2i does not exist;

[0168] R 5 , R 6 , R 7 , R 9 , R 10 and R 11 As defined with respect to formula (I);

[0169] R 1c , R 1d , R 1e , R 2c , R 2d and R 2e As defined with respect to formula (IV); and

[0170] R 1f , R 1g , R 1i , R 2f , R 2g and R 2i As defined for formula (IVa),

[0171] The condition is Not equivalent to

[0172] In some embodiments, the compound of the present disclosure is a compound of formula (Va), wherein It is a single bond.

[0173] In another embodiment, the compound of the present disclosure is a compound having formula (VI):

[0174]

[0175] or a salt or solvate thereof, wherein:

[0176] Each is a single bond or a double bond;

[0177] R 1c , R 1d , R 1e , R 2c , R 2d and R 2e are independently selected from the group consisting of hydrogen and C1-C6 alkyl; and

[0178] R 5 , R 6 , R 7 , R 9 , R 10 and R 11 As defined for formula (I),

[0179] The condition is Not equivalent to

[0180] In another embodiment, the compound of the present disclosure is a compound having Formula (VIa):

[0181]

[0182] or a salt or solvate thereof, wherein:

[0183] Each is a single bond or a double bond;

[0184] The condition is that if the connection with R 1e and R 1i Connected Carbon is a double bond, then R 1e and R 1i does not exist, and if connected with R 2e and R 2i Connected Carbon is a double bond, then R 2e and R 2i does not exist;

[0185] R 5 , R 6 , R 7 , R 9 , R 10 and R 11 As defined with respect to formula (I);

[0186] R 1c , R 1d , R1e , R 2c , R 2d and R 2e As defined with respect to formula (IV); and

[0187] R 1f , R 1g , R 1i , R 2f , R 2g and R 2i As defined for formula (IVa),

[0188] The condition is Not equivalent to

[0189] In some embodiments, the compound of the present disclosure is a compound of formula (VIa), wherein It is a single bond.

[0190] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (IV)-(VI), (IVa), (Va) or (VIa), wherein R 5 , R 6 , R 7 , R 9 , R 10 and R 11 Selected from the group consisting of hydrogen, methyl, C1-C6 alkoxy and C1-C6 alkylthio.

[0191] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (IV)-(VI), (IVa), (Va) or (VIa), wherein R 5 , R 6 , R 7 , R 9 , R 10 and R 11 It's hydrogen.

[0192] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (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.

[0193] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (IV)-(VI), (IVa), (Va) or (VIa), wherein R 1c , R 1d , R1e , R 2c , R 2d and R 2e It's methyl.

[0194] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (IV)-(VI), (IVa), (Va) or (VIa), wherein R 3a It's hydrogen.

[0195] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (IV)-(VI), (IVa), (Va) or (VIa), wherein R 3a Selected from the group consisting of: C1-C 12 alkyl,

[0196] and Q is -NH-, -O- or -S-.

[0197] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (IV)-(VI), (IVa), (Va) or (VIa), wherein R 3a It is a C1-C12 alkyl group.

[0198] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (IV)-(VI), (IVa), (Va) or (VIa), wherein R 3a It is methyl, ethyl, propyl, isopropyl, butyl, iso-butyl, sec-butyl or tert-butyl.

[0199] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (IV)-(VI), (IVa), (Va) or (VIa), wherein R 3a yes:

[0200]

[0201] In some embodiments, the compound of the present disclosure is a compound of any of Formula (IV)-(VI), (IVa), (Va), or (VIa), wherein Q is -O-.

[0202] In some embodiments, the compound of the present disclosure is any one or more of the compounds of Table 1, or a salt or solvate thereof.

[0203] Table 1

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223] The compounds of the present disclosure are useful as antidegradants, such as antiozonants and / or antioxidants, as additives in lubricants, and as additives in combustible fuels.

[0224] 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.

[0225] Solution 1

[0226]

[0227] The compounds of the present disclosure can also be prepared by the reaction of 4,4'-alkylenedianiline with methyl ketone in the presence of an acid, as shown in Scheme 2.

[0228] Solution 2

[0229]

[0230] Compounds of the present disclosure can also be prepared by reducing the compounds obtained in the reaction described in Scheme 2, as shown in Scheme 3. The reduction can be performed using any method known in the art, such as exposure to hydrogen gas over a palladium on carbon (Pd / C) catalyst.

[0231] Solution 3

[0232]

[0233] The compounds of the present disclosure can also be prepared, for example, by reacting bis(aminophenyl)methane, bis(aminophenyl)ether or bis(aminophenyl)sulfide with an olefin and an aldehyde or ketone in acetonitrile or other suitable solvent and a catalyst such as any suitable acid, base or I, i.e., via a Povarov reaction, as shown in Scheme 4, wherein R 14a , R 14b , R 14c , R 14d , R 14e and R 15f is, for example, hydrogen or C1-C6 alkyl.

[0234] Solution 4

[0235]

[0236] The compounds of the present disclosure can also be prepared by oxidizing the compounds obtained in Scheme 4 by methods known in the art, as shown in Scheme 5.

[0237] Solution 5

[0238]

[0239] definition

[0240] As used herein, the term "alkyl" by itself or as part of another group refers to a straight or branched chain aliphatic hydrocarbon containing from one to twelve carbon atoms, i.e., C1-C 12 Alkyl, or specify the number of carbon atoms, for example, C1-C3 alkyl, such as methyl, ethyl, propyl or isopropyl; C1-C4 alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl; etc. In one embodiment, the alkyl is a straight chain alkyl. In another embodiment, the alkyl is a branched chain alkyl. In one embodiment, the alkyl is a C1-C8 alkyl. In another embodiment, the alkyl is a C1-C6 alkyl. In another embodiment, the alkyl is a C1-C4 alkyl. In another embodiment, the alkyl is a C1-C3 alkyl. Non-limiting exemplary C1-C 12 Alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, 3-pentyl, hexyl, heptyl, octyl, nonyl and decyl.

[0241] As used herein, the term "halo" or "halogen" by itself or as part of another group refers to -Cl, -F, -Br or -I.

[0242] As used herein, the term "nitro" by itself or as part of another group refers to -NO2.

[0243] As used herein, the term "cyano" by itself or as part of another group refers to -CN.

[0244] As used herein, the term "hydroxy" by itself or as part of another group refers to -OH.

[0245] As used herein, the term "nitro" by itself or as part of another group refers to a radical of the formula -NR 12 R 13 A group in which R 12 and R 13 are independently hydrogen, alkyl or aryl.

[0246] In one embodiment, the amino group is -NH2.

[0247] In another embodiment, the amino group is an "alkylamino" group, ie, wherein R 12 It is C 1-6 Alkyl and R 13 In one embodiment, R 12 is a C1-C4 alkyl group. Non-limiting exemplary alkylamino groups include -N(H)CH3 and -N(H)CH2CH3.

[0248] In another embodiment, the amino group is a "dialkylamino" group, i.e., wherein R 12 and R 13 Each independently is C 1-6 In one embodiment, R 12 and R 13 Each is independently C1-C4 alkyl. Non-limiting exemplary dialkylamino groups include -N(CH3)2 and -N(CH3)CH2CH(CH3)2.

[0249] In another embodiment, the amino group is an "arylamino" group, ie, wherein R 12 is an aryl group and R 13 In one embodiment, R 12 is an optionally substituted phenyl. In another embodiment, R 12 is phenyl, 2-methylphenyl, 3-methylphenyl or 4-methylphenyl.

[0250] In another embodiment, the amino group is a "diarylamino" group, ie, wherein R 12 and R 13 Each is independently an amino group of an aryl group. 12 and R 13 It is phenyl.

[0251] As used herein, the term "aryl" by itself or as part of another group refers to an aromatic ring system having six to fourteen carbon atoms, i.e., C6-C 14 Aryl. Non-limiting exemplary aryl groups include phenyl, naphthyl, phenanthrenyl, anthracenyl, indenyl, azulenyl, biphenyl, biphenylene, and fluorenyl groups. In one embodiment, aryl is phenyl.

[0252] As used herein, the term "alkylcarbonyl" by itself or as part of another group refers to a carbonyl group, i.e., -C(=O)-, substituted with an alkyl group. In one embodiment, the alkyl group is a C1-C4 alkyl group. A non-limiting exemplary alkylcarbonyl group is -COCH3.

[0253] As used herein, the term "haloalkyl" itself or as part of another group refers to an alkyl group substituted with one or more fluorine, chlorine, bromine and / or iodine atoms. In one embodiment, the alkyl group is substituted with one, two or three fluorine and / or chlorine atoms. In another embodiment, the alkyl group is substituted with one, two or three fluorine atoms. In another embodiment, the alkyl group is a C1-C6 alkyl group and the resulting haloalkyl group is referred to as a "C1-C6 haloalkyl group". In another embodiment, the alkyl group is a C1-C4 alkyl group and the resulting haloalkyl group is referred to as a "C1-C4 haloalkyl group". In another embodiment, the alkyl group is a C1 or C2 alkyl group. Non-limiting exemplary haloalkyl groups include fluoromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, 4,4,4-trifluorobutyl and trichloromethyl groups.

[0254] As used herein, the term "alkoxy" by itself or as part of another group refers to an alkyl group attached to a terminal oxygen atom. In one embodiment, the alkyl group is a C1-C6 alkyl group, and the resulting alkoxy group is referred to as a "C1-C6 alkoxy group". In another embodiment, the alkyl group is a C1-C4 alkyl group, and the resulting alkoxy group is therefore referred to as a "C1-C4 alkoxy group". Non-limiting exemplary alkoxy groups include methoxy, ethoxy, and tert-butoxy.

[0255] As used herein, the term "alkylthio" by itself or as part of another group refers to an alkyl group attached to a terminal sulfur atom. In one embodiment, the alkyl group is a C1-alkyl group, and the resulting alkylthio group is referred to as a "C1-C6 alkylthio group". In one embodiment, the alkyl group is a C1-C4 alkyl group and the resulting alkylthio group is referred to as a "C1-C4 alkylthio group". Non-limiting exemplary alkylthio groups include -SCH3 and -SCH2CH3.

[0256] As used herein, the term "cycloalkyl" by itself or as part of another group refers to saturated and partially unsaturated (e.g., containing one or two double bonds) monocyclic, bicyclic or tricyclic aliphatic hydrocarbons containing three to twelve carbon atoms (i.e., C3-C 12 In one embodiment, the cycloalkyl group is bicyclic, i.e., it has two rings. In another embodiment, the cycloalkyl group is monocyclic, i.e., it has one ring. In another embodiment, the cycloalkyl group is a C3-C8 cycloalkyl group. In another embodiment, the cycloalkyl group is a C3-C6 cycloalkyl group. In another embodiment, the cycloalkyl group is a C5 cycloalkyl group, i.e., cyclopentyl group. In another embodiment, the cycloalkyl group is a C6 cycloalkyl group, i.e., cyclohexyl group. Non-limiting exemplary C3-C 12 Cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, norbornyl, decalin, adamantyl, cyclohexenyl and spiro[3.3]heptane.

[0257] As used herein, the term "optionally substituted phenyl" by itself or as part of another group refers to phenyl that is unsubstituted or substituted with one to five substituents, wherein each of the substituents is independently halo, nitro, cyano, hydroxy, amino (e.g., -NH2, alkylamino, dialkylamino, arylamino, or diarylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl, or cycloalkyl.

[0258] As used herein, the term "heterocycle" by itself or as part of another group refers to a saturated and partially unsaturated (e.g., containing one or two double bonds) monocyclic, bicyclic or tricyclic group containing three to eighteen ring members, i.e., a 3- to 18-membered heterocycle, containing one, two, three or four 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, including cyclic urea groups (such as imidazolidinyl-2-one), cyclic amide groups (such as pyrrolidin-2-one or piperidine-2-one) and cyclic carbamate groups (such as oxazolidinyl-2-one). The term heterocycle also includes groups with fused optionally substituted aryl or optionally substituted heteroaryl groups 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]azepine -2-ketone. 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.

[0259] As used herein, the term "optionally substituted heterocycle" by itself or as part of another group refers to a heterocycle group that is unsubstituted or substituted with one to four substituents, said substituents being independently halo, nitro, cyano, hydroxy, amino (e.g., -NH2, alkylamino or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl, or cycloalkyl.

[0260] As used herein, the term "heteroaryl" itself or as part of another group refers to a monocyclic aromatic ring system with five to six ring members, i.e., a 5 to 6-membered heteroaryl containing one, two, three, four or five heteroatoms. Each heteroatom is independently oxygen, sulfur or nitrogen. In one embodiment, the heteroaryl has three heteroatoms. In another embodiment, the heteroaryl has two heteroatoms. In another embodiment, the heteroaryl has one heteroatom. In another embodiment, the heteroaryl has 5 ring atoms, for example, furanyl, i.e., a 5-membered heteroaryl with four carbon atoms and one oxygen atom. In another embodiment, the heteroaryl has 6 ring atoms, for example, pyridyl, i.e., a 6-membered heteroaryl with five carbon atoms and one nitrogen atom. Non-limiting exemplary heteroaryl groups include thienyl, furanyl, pyranyl, 2H-pyrrolyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, thiazolyl, isothiazolyl and isoxazolyl. In one embodiment, heteroaryl is selected from thienyl (e.g., thien-2-yl and thien-3-yl), furanyl (e.g., 2-furanyl and 3-furanyl), pyrrolyl (e.g., 1H-pyrrol-2-yl and 1H-pyrrol-3-yl), imidazolyl (e.g., 2H-imidazol-2-yl and 2H-imidazol-4-yl), pyrazolyl (e.g., 1H-pyrazol-3-yl, 1H-pyrazol-4-yl and 1H-pyrazol-5-yl), pyridinyl (e.g., pyridin-2-yl, pyridin-3-yl, The term heteroaryl also includes N-oxides. A non-limiting exemplary N-oxide is pyridyl N-oxide.

[0261] As used herein, the term "optionally substituted heteroaryl" by itself or as part of another group refers to heteroaryl that is unsubstituted or substituted with one to four substituents, wherein the substituents are independently halo, nitro, cyano, hydroxy, amino (e.g., -NH2, alkylamino or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl, or cycloalkyl.

[0262] As used herein, the term "stereoisomer" 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 of compounds that have more than one chiral center and are not mirror images of each other (diastereomers).

[0263] The term "chiral center" or "asymmetric carbon atom" refers to a carbon atom to which four different groups are attached.

[0264] The terms "enantiomer" and "enantiomeric" refer to molecules that are not superimposable on their mirror images and therefore optically active wherein the enantiomer rotates the plane of polarized light in one direction and its mirror image compound rotates the plane of polarized light in the opposite direction.

[0265] The term "racemic" refers to a mixture of equal parts of enantiomers and the mixture is optically inactive.

[0266] The term "absolute configuration" refers to the spatial arrangement of atoms of a chiral molecular entity (or group) and its stereochemical description, for example, R or S.

[0267] Unless otherwise indicated, stereochemical terminology and conventions used in the specification are intended to be consistent with those described in Pure & Appl. Chem 68:2193 (1996).

[0268] The term "enantiomeric excess" or "ee" refers to a measure of how much of one enantiomer is present compared to the other. For a mixture of R and S enantiomers, the percent enantiomeric excess is defined as |RS|*100, where R and S are the respective mole or weight fractions of the enantiomers in the mixture such that R+S=1. Based on the knowledge of the optical rotations of chiral substances, the percent enantiomeric excess is defined as ([α]obs / / [α]max)*100, where [α]obs is the optical rotation of the mixture of enantiomers and [α]max is the optical rotation of the pure enantiomer. Enantiomeric excess can be determined using a variety of analytical techniques including NMR spectroscopy, chiral column chromatography, or optical polarimetry.

[0269] In thin layer chromatography (TLC), the term Rf stands for retention factor. Rf is defined as the distance traveled by a single component divided by the total distance traveled by the eluent. Its value is always between zero and one.

[0270] Salts and solvates (eg, hydrates) of the disclosed compounds may also be used in the methods disclosed herein.

[0271] The present disclosure encompasses the preparation and use of salts of compounds of the present disclosure. Salts of compounds of the present disclosure can be prepared during the final separation and purification of the compounds, or prepared separately by reacting the compounds with an acid having a suitable cation. The salts of compounds of the present disclosure can be acid addition salts formed with acceptable acids. Examples of acids that can be used to form salts include inorganic acids (such as nitric acid, boric acid, hydrochloric acid, hydrobromic acid, sulfuric acid and phosphoric acid) and organic acids (such as oxalic acid, maleic acid, succinic acid and citric acid). Non-limiting examples of salts of compounds of the present disclosure include, but are not limited to, hydrochloride, hydrobromide, hydroiodide, sulfate, bisulfate, 2-hydroxyethanesulfonate, phosphate, hydrogenphosphate, acetate, adipate, alginate, aspartate, benzoate, bisulfate, butyrate, camphorate, camphorsulfonate, digluconate, glycerophosphate, hemisulfate, heptanoate, hexanoate, formate, succinate, fumarate, maleate, ascorbate, isethionate, salicylate, methanesulfonate, mesitylenesulfonate, naphthylenesulfonate, nicotinate, 2-naphthalenesulfonate, oxalate, pamoate, pectinate, persulfate, 3-phenylpropionate, picrate, pivalate, propionate, trichloroacetate, trifluoroacetate, phosphate, glutamate, bicarbonate, undecanoate, lactate, citrate, tartrate, gluconate, methanesulfonate, edisylate, benzenesulfonate, and p-toluenesulfonate. In addition, available amino groups present in the compounds of the present disclosure may be quaternized with methyl, ethyl, propyl and butyl chlorides, bromides and iodides; dimethyl, diethyl, dibutyl and diamyl sulfates; decyl, lauryl, myristyl and stearyl chlorides, bromides and iodides; and benzyl and phenethyl bromides. In view of the foregoing, any reference to the compounds of the present disclosure appearing herein is intended to include the compounds of the present disclosure and salts, hydrates or solvates thereof.

[0272] The present disclosure encompasses the preparation and use of solvates of compounds of the present disclosure. As used herein, the term "solvate" is a combination, physical association and / or solvation of a compound of the present disclosure with a solvent molecule, such as a disolvate, a monosolvate or a hemisolvate, wherein the ratio of solvent molecules to the compounds of the present disclosure is about 2:1, about 1:1 or about 1:2, respectively. This physical association involves varying degrees of ionic bonding and covalent bonding, including hydrogen bonding. In some cases, such as when one or more solvent molecules are incorporated into the lattice of a crystalline solid, the solvate can be separated. Therefore, "solvate" includes a solution phase and a separable solvate. The compounds of the present disclosure may exist in a solvated form with a solvent (such as water, methanol and ethanol), and the present disclosure is intended to include solvated and non-solvated forms of the compounds of the present disclosure.

[0273] A solvate is a hydrate. "Hydrate" refers to a specific subgroup of solvates in which the solvent molecule is water. The preparation of solvates is known in the art. See, for example, M. Caira et al., J. Pharmaceut. Sci., 93 (3): 601-611 (2004), which describes the preparation of solvates of fluconazole with ethyl acetate and water. Similar preparations of solvates, hemisolvates, hydrates, etc. are described by van Tonder et al., AAPS Pharm. Sci. Tech., 5 (1): Article 12 (2004) and AL Bingham et al., Chem. Commun. 603-604 (2001). A typical non-limiting process for preparing a solvate will involve dissolving the compound of the present disclosure in a desired solvent (organic solvent, water or a mixture thereof) at a temperature above 20°C to about 25°C, then cooling the solution at a rate sufficient to form crystals, and separating the crystals by known methods (e.g., filtration). Analytical techniques such as infrared spectroscopy can be used to confirm the presence of solvent in solvate crystals.

[0274] Unless otherwise stated, in the context of describing the present disclosure (especially in the context of the claims), the use of the terms "a / an", "the" and similar references should be interpreted to cover both the singular and the plural. Unless otherwise stated herein, references to ranges of values ​​herein are intended only to serve as a shorthand method of individually referring to each individual value within the range, and each individual value is incorporated into the specification as if it were individually cited herein. Unless otherwise stated, the use of any and all examples or exemplary language (e.g., "such as") provided herein is intended to better illustrate the present disclosure rather than to limit the scope of the present disclosure. No language in the specification should be interpreted as indicating any unclaimed element as being necessary to practice the present disclosure.

[0275] As used herein, the term "wt / wt%" refers to the mass of one component in a composition or blend, e.g., a composition comprising a compound of the present disclosure and one or more elastomers; or a composition of the present disclosure and one or more fillers; or a blend comprising two or more elastomers, etc., divided by the total mass of all components in the composition or blend multiplied by 100. For example, in a composition comprising 1 kg of the compound, 1 kg of natural rubber, and 2 kg of synthetic rubber, the wt / wt% of the compound of the present disclosure is 25 wt / wt% (1 kg / 4 kg = 0.25 x 100 = 25 wt / wt%). In a composition comprising 1 kg of the compound and 1 kg of carbon black, the wt / wt% of the compound of the present disclosure is 50 wt / wt% (1 kg / 2 kg = 0.20 x 100 = 50 wt / wt%). In a composition comprising 1 kg of compound, 1 kg of natural rubber, 2 kg of synthetic rubber and 1 kg of carbon black, the weight / weight % of the disclosed compound is 20 weight / weight % (1 kg / 5 kg = 0.20 x 100 = 20 weight / weight %). In a blend of one or more elastomers comprising 20 kg of natural rubber and 30 kg of synthetic rubber, the weight / weight % of natural rubber is 40 weight / weight % (20 kg / 50 kg = 0.40 x 100 = 40 weight / weight %).

[0276] Compositions and methods of use

[0277] In another embodiment, the present disclosure provides a composition comprising:

[0278] (i) a compound of the present disclosure; and

[0279] (ii) one or more elastomers; or

[0280] (iii) one or more fillers; or

[0281] (iv) one or more rubber chemicals; or

[0282] (v) one or more plasticizers; or

[0283] (vi) a second antidegradant; or

[0284] (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 antidegradant.

[0285] In some embodiments, the compositions of the present disclosure comprise from about 15 wt / wt% to about 85 wt / wt% of a compound of the present disclosure. In some embodiments, the composition comprises from about 1 wt / wt% to about 5 wt / wt%, from about 1 wt / wt% to about 15 wt / wt%, from about 1 wt / wt% to about 25 wt / wt%, from about 1 wt / wt% to about 35 wt / wt%, from about 1 wt / wt% to about 45 wt / wt%, from about 1 wt / wt% to about 55 wt / wt%, from about 1 wt / wt% to about 65 wt / wt%, from about 1 wt / wt% to about 75 wt / wt%, from about 1 wt / wt% to about 85 wt / wt%, from about 1 wt / wt% to about 95 wt / wt%, from about 5 wt / wt% to about 15 wt / wt%, from about 5 wt / wt% to about 25 wt / wt%, %, about 5 wt / wt% to about 35 wt / wt%, about 5 wt / wt% to about 45 wt / wt%, about 5 wt / wt% to about 55 wt / wt%, about 5 wt / wt% to about 65 wt / wt%, about 5 wt / wt% to about 75 wt / wt%, about 5 wt / wt% to about 85 wt / wt%, about 5 wt / wt% to about 95 wt / wt%, about 15 wt / wt% to about 25 wt / wt%, about 15 wt / wt% to about 35 wt / wt%, about 15 wt / wt% to about 45 wt / wt%, about 15 wt / wt% to about 55 wt / wt%, about 15 wt / wt% to about 65 wt / wt%, about 1 %, about 25 wt / wt% to about 75 wt / wt%, about 15 wt / wt% to about 95 wt / wt%, about 25 wt / wt% to about 35 wt / wt%, about 25 wt / wt% to about 45 wt / wt%, about 25 wt / wt% to about 55 wt / wt%, about 25 wt / wt% to about 65 wt / wt%, about 25 wt / wt% to about 75 wt / wt%, about 25 wt / wt% to about 85 wt / wt%, about 25 wt / wt% to about 95 wt / wt%, about 35 wt / wt% to about 45 wt / wt%, about 35 wt / wt% to about 55 wt / wt%, about 35 wt / wt% to about 65 wt / wt%, about %, about 35 wt / wt% to about 75 wt / wt%, about 35 wt / wt% to about 85 wt / wt%, about 35 wt / wt% to about 95 wt / wt%, about 45 wt / wt% to about 55 wt / wt%, about 45 wt / wt% to about 65 wt / wt%, about 45 wt / wt% to about 75 wt / wt%, about 45 wt / wt% to about 85 wt / wt%, about 45 wt / wt% to about 95 wt / wt%, about 55 wt / wt% to about 65 wt / wt%, about 55 wt / wt% to about 75 wt / wt%, about 55 wt / wt% to about 85 wt / wt%, about 55 wt / wt% to about 95 wt / wt%,About 65 w / w % to about 75 w / w %, about 65 w / w % to about 85 w / w %, about 65 w / w % to about 95 w / w %, about 75 w / w % to about 85 w / w %, about 75 w / w % to about 95 w / w %, or about 85 w / w % to about 95 w / w % of the compounds of the present disclosure. In some embodiments, the composition comprises from about 0.1 w / w% to about 0.5 w / w%, from about 0.1 w / w% to about 1 w / w%, from about 0.1 w / w% to about 1.5 w / w%, from about 0.1 w / w% to about 2 w / w%, from about 0.1 w / w% to about 2.5 w / w%, from about 0.1 w / w% to about 3 w / w%, from about 0.1 w / w% to about 3.5 w / w%, from about 0.1 w / w% to about 4 w / w%, from about 0.1 w / w% to about 4.5 w / w%, from about 0.1 w / w% to about 4.5 w / w%. %, about 0.5 wt / wt% to about 1 wt / wt%, about 0.5 wt / wt% to about 2 wt / wt%, about 0.5 wt / wt% to about 3 wt / wt%, about 0.5 wt / wt% to about 4 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 0.1 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 %, 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%, about 1.5 wt / wt% to about 2 wt / wt%, about 1 wt / wt% to about 3 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%, about 1.5 wt / wt% to about 2 wt / wt%,about 1.5 wt / wt% to about 2.5 wt / wt%, about 1.5 wt / wt% to about 3 wt / wt%, about 1.5 wt / wt% to about 3.5 wt / wt%, about 1.5 wt / wt% to about 4 wt / wt%, about 1.5 wt / wt% to about 4.5 wt / wt%, about 1.5 wt / wt% to about 5 wt / wt%, about 1.5 wt / wt% to about 6 wt / wt%, about 1.5 wt / wt% to about 7 wt / wt%, about 1.5 wt / wt% to about 8 wt / wt%, about 1.5 wt / wt% to about 9 wt / wt%, about 1.5 wt / wt% to about 10 wt / wt%, about 2 wt / wt% to about 2.5 wt / wt% %, about 2 wt / wt% to about 3 wt / wt%, about 2 wt / wt% to about 3.5 wt / wt%, about 2 wt / wt% to about 4 wt / wt%, about 2 wt / wt% to about 4.5 wt / wt%, about 2 wt / wt% to about 5 wt / wt%, about 2 wt / wt% to about 6 wt / wt%, about 2 wt / wt% to about 7 wt / wt%, about 2 wt / wt% to about 8 wt / wt%, about 2 wt / wt% to about 9 wt / wt%, about 2 wt / wt% to about 10 wt / wt%, about 2.5 wt / wt% to about 3 wt / wt%, about 2.5 wt / wt% to about 3.5 wt / wt%, about 2.5 wt / wt% to about 4 wt / wt%, %, about 2.5 w / w % to about 4.5 w / w %, about 2.5 w / w % to about 5 w / w %, about 2.5 w / w % to about 6 w / w %, about 2.5 w / w % to about 7 w / w %, about 2.5 w / w % to about 8 w / w %, about 2.5 w / w % to about 9 w / w %, about 2.5 w / w % to about 10 w / w %, about 3 w / w % to about 4 w / w %, about 3 w / w % to about 4.5 w / w %, about 3 w / w % to about 5 w / w %, about 3 w / w % to about 6 w / w %, about 3 w / w % to about 7 w / w %, about 3 w / w % to about About 8 wt / wt%, about 3 wt / wt% to about 9 wt / wt%, about 3 wt / wt% to about 10 wt / wt%, about 3.5 wt / wt% to about 4 wt / wt%, about 3.5 wt / wt% to about 4.5 wt / wt%, about 3.5 wt / wt% to about 5 wt / wt%, about 3.5 wt / wt% to about 6 wt / wt%, about 3.5 wt / wt% to about 7 wt / wt%, about 3.5 wt / wt% to about 8 wt / wt%, about 3.5 wt / wt% to about 9 wt / wt%, about 3.5 wt / wt% to about 10 wt / wt%, about 4 wt / wt% to about 4.5 wt / wt%, about 4 wt / wt% to about 5 wt / wt%,About 4 wt / wt% to about 6 wt / wt%, about 4 wt / wt% to about 7 wt / wt%, about 4 wt / wt% to about 8 wt / wt%, about 4 wt / wt% to about 9 wt / wt%, about 4 wt / wt% to about 10 wt / wt%, about 4.5 wt / wt% to about 5 wt / wt%, about 4.5 wt / wt% to about 6 wt / wt%, about 4.5 wt / wt% to about 7 wt / wt%, about 4.5 wt / wt% to about 8 wt / wt%, about 4.5 wt / wt% to about 9 wt / wt%, about 4.5 wt / wt% to about 10 wt / wt%, about 5 wt / wt% to about 6 wt / wt%, about 5 wt / wt% to about 7 wt / wt%, About 5 wt / wt% to about 8 wt / wt%, about 5 wt / wt% to about 9 wt / wt%, about 5 wt / wt% to about 10 wt / wt%, about 6 wt / wt% to about 7 wt / wt%, about 6 wt / wt% to about 8 wt / wt%, about 6 wt / wt% to about 9 wt / wt%, about 6 wt / wt% to about 10 wt / wt%, about 7 wt / wt% to about 8 wt / wt%, about 7 wt / wt% to about 9 wt / wt%, about 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% of a compound of the disclosure.

[0286] In some embodiments, the composition of the present disclosure comprises about 50% w / w of the compound of the present disclosure. In some embodiments, the composition comprises about 1% w / w, about 5% w / w, about 10% w / w, about 15% w / w, about 20% w / w, about 25% w / w, about 30% w / w, about 35% w / w, about 40% w / w, about 45% w / w, about 55% w / w, about 60% w / w, about 65% w / w, about 70% w / w, about 75% w / w, about 80% w / w, about 85% w / w, about 90% w / w, or about 95% w / w of the 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 a compound of the disclosure.

[0287] In some embodiments, the compositions of the present disclosure comprise Compound 1, Compound 2, Compound 4, Compound 5, or Compound 6, Compound 11, Compound 19, Compound 27, Compound 30, Compound 31, or Compound 32.

[0288] In another embodiment, a composition of the present disclosure comprises a compound of the present disclosure and one or more elastomers.

[0289] As used herein, the term "elastomer" is a polymer with viscoelasticity (i.e., having both viscosity and elasticity), which generally has low intermolecular forces, low Young's modulus, and high failure strain. Elastomers can generally be cross-linked by heating in the presence of one or more cross-linking agents, a process known as curing or vulcanization. Rubber is a type of elastomer. Non-limiting types of rubber include natural rubber (NR), synthetic rubber, and blends thereof. As used herein, the term "natural rubber" refers to a naturally occurring elastomer that can be obtained from a rubber tree. Non-limiting types of synthetic rubber include unsaturated rubber, saturated rubber, rubber (FKM) with fluorine and fluoroalkyl or fluoroalkoxy substituent groups on the polymer chain, silicone rubber (Q), and blends thereof. Non-limiting examples of unsaturated rubber include polyisoprene rubber (IR), butyl rubber (IIR), polybutadiene rubber (BR), styrene-isoprene-butadiene rubber (SIBR), styrene-butadiene rubber (SBR), nitrile rubber (NBR), chloroprene rubber (CR), ethylene-propylene-diene rubber (EPDM), and blends thereof. These unsaturated rubbers undergo cyclization and crosslinking reactions, resulting in hardening of aged parts. As oxidation occurs, these vulcanized rubbers harden and eventually become brittle products. Partial oxidation can lead to performance loss when vulcanized rubbers are used in applications such as vehicle tire sidewalls. Saturated rubbers are rubbers that do not contain C=C unsaturation, and include but are not limited to acrylic rubber (ACM), chlorinated polyethylene (CM), chlorosulfonated polyethylene (CSM), polychloromethyl ethylene oxide (CO), ethylene-ethyl acrylate copolymer (EAM), epichlorohydrin rubber (ECO), ethylene propylene rubber (EPM), ethylene vinyl acetate copolymer (EVM), rubbers with fluorine and fluoroalkyl or fluoroalkoxy substituent groups on the polymer chain (FKM), silicone rubber (Q) and blends thereof.

[0290] In some embodiments, natural rubber includes rubber derived from alternative rubber plants. As used herein, the term "natural rubber includes rubber derived from alternative rubber plants" refers to naturally occurring elastomers that can be obtained from "non-rubber tree" sources. In some embodiments, the alternative rubber plant is Parthenium argentatum (guayule) or Taraxacum kok-saghyz (Russian dandelion).

[0291] In some embodiments, the one or more elastomers further include reclaimed rubber. As used herein, the term "reclaimed rubber" refers to an elastomer that is recovered from waste materials such as scrap tires.

[0292] In some embodiments, the compositions of the present disclosure include about 15 wt / wt% to about 85 wt / wt% of one or more elastomers. In some embodiments, the compositions include about 1 wt / wt% to about 5 wt / wt%, about 1 wt / wt% to about 15 wt / wt%, about 1 wt / wt% to about 25 wt / wt%, about 1 wt / wt% to about 35 wt / wt%, about 1 wt / wt% to about 45 wt / wt%, about 1 wt / wt% to about 55 wt / wt%, about 1 wt / wt% to about 65 wt / wt%, about 1 wt / wt% to about 75 wt / wt%, about 1 wt / wt% to about 85 wt / wt%, about 1 wt / wt% to about 95 wt / wt%, about 5 wt / wt% to about 15 wt / wt%, about 5 wt / wt% to about %, about 5 wt / wt% to about 65 wt / wt%, about 5 wt / wt% to about 75 wt / wt%, about 5 wt / wt% to about 85 wt / wt%, about 5 wt / wt% to about 95 wt / wt%, about 15 wt / wt% to about 25 wt / wt%, about 15 wt / wt% to about 35 wt / wt%, about 15 wt / wt% to about 45 wt / wt%, about 15 wt / wt% to about 55 wt / wt%, about 15 wt / wt% to about 65 wt / wt%, about 5 wt / wt% to about 75 wt / wt%, about 5 wt / wt% to about 85 wt / wt%, about 5 wt / wt% to about 95 wt / wt%, about 15 wt / wt% to about 25 wt / wt%, about 15 wt / wt% to about 35 wt / wt%, about 15 wt / wt% to about 45 wt / wt%, about 15 wt / wt% to about 55 wt / wt%, about 15 wt / wt% to about %, about 15 wt / wt% to about 75 wt / wt%, about 15 wt / wt% to about 95 wt / wt%, about 25 wt / wt% to about 35 wt / wt%, about 25 wt / wt% to about 45 wt / wt%, about 25 wt / wt% to about 55 wt / wt%, about 25 wt / wt% to about 65 wt / wt%, about 25 wt / wt% to about 75 wt / wt%, about 25 wt / wt% to about 85 wt / wt%, about 25 wt / wt% to about 95 wt / wt%, about 35 wt / wt% to about 45 wt / wt%, about 35 wt / wt% to about 55 wt / wt%, about 35 wt / wt% to about 65 wt / wt%, about 25 wt / wt% to about 75 wt / wt%, about 25 wt / wt% to about 85 wt / wt%, about 25 wt / wt% to about 95 wt / wt%, about 35 wt / wt% to about 45 wt / wt%, about 35 wt / wt% to about 55 wt / wt%, about 35 wt / wt% to about % to about 65 wt / wt%, about 35 wt / wt% to about 75 wt / wt%, about 35 wt / wt% to about 85 wt / wt%, about 35 wt / wt% to about 95 wt / wt%, about 45 wt / wt% to about 55 wt / wt%, about 45 wt / wt% to about 65 wt / wt%, about 45 wt / wt% to about 75 wt / wt%, about 45 wt / wt% to about 85 wt / wt%, about 45 wt / wt% to about 95 wt / wt%, about 55 wt / wt% to about 65 wt / wt%, about 55 wt / wt% to about 75 wt / wt%, about 55 wt / wt% to about 85 wt / wt%,About 55 wt / wt% to about 95 wt / wt%, about 65 wt / wt% to about 75 wt / wt%, about 65 wt / wt% to about 85 wt / wt%, about 65 wt / wt% to about 95 wt / wt%, about 75 wt / wt% to about 85 wt / wt%, about 75 wt / wt% to about 95 wt / wt%, or about 85 wt / wt% to about 95 wt / wt% of one or more elastomers.

[0293] In some embodiments, the composition of the present disclosure comprises about 50 wt / wt% of one or more elastomers. In some embodiments, the composition comprises about 1 wt / wt%, about 5 wt / wt%, about 10 wt / wt%, about 15 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt% of one or more elastomers.

[0294] As used herein, the term "phr" means parts by weight per hundred parts of rubber. The parts by weight of each component are based on 100 parts by weight of the total mass of the one or more elastomers present in the composition.

[0295] In some embodiments, the compositions of the present disclosure comprise from about 1 phr to about 5 phr of a 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 to about 20 phr, about 0.1 phr to about 0.5 phr, about 0.1 phr to about 1 phr, about 0.1 phr to about 2 phr, about 0.1 phr to about 3 phr, about 0.1 phr to about 4 phr, about 0.1 phr to about 5 phr, about 0.1 phr to about 7.5 phr, about 0.1 phr to about 10 phr, about 0.1 phr to about 20 phr, about 1 phr to about 2 phr, about 1 phr to about 3 phr, about 1 phr to about hr to about 4phr, about 1phr to about 7.5phr, about 1phr to about 10phr, about 1phr to about 20phr, about 2phr to about 3phr, about 2phr to about 4phr, about 2phr to about 5phr, about 2phr to about 7.5phr, about 2phr to about 10phr, about 2phr to about 20phr, about 3phr to about 4phr, about 3phr to about 5phr, about 3phr to about 7.5phr, about 2phr to about 10phr, about 2phr to about 20phr, about 3phr to about 4phr, about 3phr to about 5phr, about 3phr to about 7.5phr, about 3phr to about The invention further comprises a compound of the present disclosure in an amount of about 1 phr to about 10 phr, about 3 phr to about 20 phr, about 4 phr to about 5 phr, about 4 phr to about 7.5 phr, about 4 phr to about 10 phr, about 4 phr to about 20 phr, about 5 phr to about 7.5 phr, about 5 phr to about 10 phr, about 5 phr to about 20 phr, about 7.5 phr to about 10 phr, about 7.5 phr to about 20 phr, or about 10 phr to about 20 phr of a compound of the present disclosure.

[0296] In some embodiments, the compositions of the present disclosure comprise about 3 phr of a compound of the present disclosure. In some embodiments, the composition comprises about 0.01 phr, about 0.1 phr, about 0.5 phr, about 1 phr, about 2 phr, about 3 phr, about 4 phr, about 5 phr, about 7.5 phr, about 10 phr, or about 20 phr of a compound of the present disclosure.

[0297] In some embodiments, compositions of the present disclosure include a compound of the present disclosure and one or more fillers.

[0298] As used herein, the term "filler" is a substance that strengthens an elastomeric composition or imparts other properties to the elastomeric composition, including but not limited to expanding the volume of the composition. Non-limiting examples of fillers include carbon black, silica, kaolin, calcium silicate, talc, carbon nanotubes (CNT), carbon fibers (HCF), graphite, graphene, aluminosilicates, starch and fibers, and combinations thereof.

[0299] In some embodiments, the filler is derived from a natural source. For example, the silica may be derived from rice husks.

[0300] In some embodiments, the compositions of the present disclosure comprise from about 15 wt / wt% to about 85 wt / wt% of one or more fillers. In some embodiments, the compositions comprise 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 %, about 5 wt / wt% to about 65 wt / wt%, about 5 wt / wt% to about 75 wt / wt%, about 5 wt / wt% to about 85 wt / wt%, about 5 wt / wt% to about 95 wt / wt%, about 15 wt / wt% to about 25 wt / wt%, about 15 wt / wt% to about 35 wt / wt%, about 15 wt / wt% to about 45 wt / wt%, about 15 wt / wt% to about 55 wt / wt%, about 15 wt / wt% to about 65 wt / wt%, about 5 wt / wt% to about 75 wt / wt%, about 5 wt / wt% to about 85 wt / wt%, about 5 wt / wt% to about 95 wt / wt%, about 15 wt / wt% to about 25 wt / wt%, about 15 wt / wt% to about 35 wt / wt%, about 15 wt / wt% to about 45 wt / wt%, about 15 wt / wt% to about 55 wt / wt%, about 15 wt / wt% to about %, about 15 wt / wt% to about 75 wt / wt%, about 15 wt / wt% to about 95 wt / wt%, about 25 wt / wt% to about 35 wt / wt%, about 25 wt / wt% to about 45 wt / wt%, about 25 wt / wt% to about 55 wt / wt%, about 25 wt / wt% to about 65 wt / wt%, about 25 wt / wt% to about 75 wt / wt%, about 25 wt / wt% to about 85 wt / wt%, about 25 wt / wt% to about 95 wt / wt%, about 35 wt / wt% to about 45 wt / wt%, about 35 wt / wt% to about 55 wt / wt%, about 35 wt / wt% to about 65 wt / wt%, about 25 wt / wt% to about 75 wt / wt%, about 25 wt / wt% to about 85 wt / wt%, about 25 wt / wt% to about 95 wt / wt%, about 35 wt / wt% to about 45 wt / wt%, about 35 wt / wt% to about 55 wt / wt%, about 35 wt / wt% to about % to about 65 wt / wt%, about 35 wt / wt% to about 75 wt / wt%, about 35 wt / wt% to about 85 wt / wt%, about 35 wt / wt% to about 95 wt / wt%, about 45 wt / wt% to about 55 wt / wt%, about 45 wt / wt% to about 65 wt / wt%, about 45 wt / wt% to about 75 wt / wt%, about 45 wt / wt% to about 85 wt / wt%, about 45 wt / wt% to about 95 wt / wt%, about 55 wt / wt% to about 65 wt / wt%, about 55 wt / wt% to about 75 wt / wt%, about 55 wt / wt% to about 85 wt / wt%,About 55 wt / wt% to about 95 wt / wt%, about 65 wt / wt% to about 75 wt / wt%, about 65 wt / wt% to about 85 wt / wt%, about 65 wt / wt% to about 95 wt / wt%, about 75 wt / wt% to about 85 wt / wt%, about 75 wt / wt% to about 95 wt / wt%, or about 85 wt / wt% to about 95 wt / wt% of one or more fillers.

[0301] In some embodiments, the composition of the present disclosure comprises about 50 wt / wt% of one or more fillers. In some embodiments, the composition comprises about 1 wt / wt%, about 5 wt / wt%, about 10 wt / wt%, about 15 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt% or about 95 wt / wt% of one or more fillers.

[0302] In some embodiments, the compositions of the present disclosure include from about 30 phr to about 500 phr of one or more fillers. In some embodiments, the compositions include 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, phr, about 50 phr to about 300 phr, about 50 phr to about 350 phr, about 50 phr to about 400 phr, about 50 phr to about 450 phr, about 50 phr to about 500 phr, about 100 phr to about 150 phr, about 100 phr to about 200 phr, about 100 phr to about 250 phr, about 100 phr to about 300 phr, about 100 phr to about 350 phr, about 100 phr to about 400 phr, about 100 phr to about 450 phr, about 100 phr to about 500 phr, about 150 phr to about 200 phr phr, about 150 phr to about 250 phr, about 150 phr to about 300 phr, about 150 phr to about 350 phr, about 150 phr to about 400 phr, about 150 phr to about 450 phr, about 150 phr to about 500 phr, about 200 phr to about 250 phr, about 200 phr to about 300 phr, about 200 phr to about 350 phr, about 200 phr to about 400 phr, about 200 phr to about 450 phr, about 200 phr to about 500 phr, about 250 phr to about 300 phr, about 250 phr to about 350 phr, From about 0 phr to about 150 phr, from about 150 phr to about 200 phr, from about 250 phr to about 400 phr, from about 250 phr to about 450 phr, from about 250 phr to about 500 phr, from about 300 phr to about 350 phr, from about 300 phr to about 400 phr, from about 300 phr to about 450 phr, from about 300 phr to about 500 phr, from about 350 phr to about 400 phr, from about 350 phr to about 450 phr, from about 350 phr to about 500 phr, from about 400 phr to about 450 phr, from about 400 phr to about 500 phr, or from about 450 phr to about 500 phr of one or more fillers.

[0303] In some embodiments, the compositions of the present disclosure include about 300 phr of one or more fillers. In some embodiments, the compositions include about 30 phr, about 50 phr, about 100 phr, about 150 phr, about 200 phr, about 250 phr, about 350 phr, about 400 phr, about 450 phr, or about 500 phr of one or more fillers.

[0304] In some embodiments, the composition of the present disclosure comprises a compound of the present disclosure and one or more rubber chemicals. As used herein, the term "rubber chemicals" refers to a compound or substance used to promote rubber vulcanization. Rubber chemicals include but are not limited to vulcanizing agents, accelerators, activators, and pre-vulcanization inhibitors.

[0305] As used herein, the term "vulcanization" refers to the process of forming crosslinks between elastomers to achieve changes in the material properties of the elastomer. Specifically, vulcanization usually increases the rigidity and durability of the elastomer. Vulcanization is carried out at room temperature or high temperature, depending on the properties of the one or more elastomers, one or more fillers and one or more rubber chemicals used. The term "curing" is also used in the art to describe this process.

[0306] As used herein, the term "vulcanizing agent" refers to any substance that can make crosslinking between elastomers. Vulcanizing agent can realize crosslinking between the independent polymer chains of elastomers by various mechanisms, including but not limited to by forming a covalent bond between vulcanizing agent and two or more independent polymer chains, or by generating a free radical substance that can be combined to form a covalent bond between two polymer chains on an independent polymer chain. The limiting examples of vulcanizing agent include sulfur, peroxide, sulfurized vegetable oil, ointment and resin. The limiting examples of sulfur include octasulfur (S8), cyclododecyl sulfide (S12) and polymeric sulfur. Non-limiting examples of peroxides include benzoyl peroxide, dicumyl peroxide (DC), 2,5-dimethyl-2,5-di-(tert-butylperoxy)-3-hexyne (2,5Tri), 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 adhesive resins. As used herein, the term "adhesive resin" refers to chemicals that react with methylene donors (such as hexamethylenetetramine (HMTA) or hexamethoxymethylmelamine (HMMM)) to promote adhesion, such as resorcinol formaldehyde resins and phenolic resins.

[0307] As used herein, the term "accelerator" refers to any material that increases the kinetics of vulcanization. In some embodiments, the accelerator enables vulcanization to be carried out at a relatively low temperature and / or more effectively utilizes a vulcanizing agent (such as sulfur). The limiting examples of accelerators include guanidine, thiazole, sulfenamide, thiuram, dithiocarbamate, xanthate and thiophosphate. The limiting examples of guanidine include diphenylguanidine (DPG). The limiting examples of thiazole include 2-mercaptobenzothiazole (MBT), 2-mercaptobenzothiazole zinc (ZMBT), mercaptobenzothiazole disulfide (MBTS) and N-tert-butyl-2-benzothiazole sulfenimide (TBSI). Non-limiting examples of sulfenamides include N-tert-butyl-2-benzothiazolesulfenamide (TBBS), N-cyclohexylbenzothiazole-2-sulfenamide (CBS), dicyclohexyl-2-benzothiazolesulfenamide (DCBS), N-oxydivinylbenzothiazolesulfenamide (OBTS), N-oxydivinylthiocarbamoyl-N'-oxydivinylsulfenamide (OTOS) and thiocarbamoylsulfenamide. Non-limiting examples of thiurams include dimethylthiocarbamic acid dithioperoxyanhydride (thiram), dipentamethylenethiuram tetrasulfide (DPIT), tetrabenzylthiuram disulfide (TBzTD), tetraethylthiuram disulfide (TETD), tetramethylthiuram disulfide (TMTD) and tetramethylthiuram monosulfide (TMTM). Non-limiting examples of dithiocarbamates include zinc dimethyldithiocarbamate (ZDMC), zinc diethyldithiocarbamate (ZDEC), zinc dibutyldithiocarbamate (ZDBC), nickel dibutyldithiocarbamate (NDBC), sodium dibenzyldithiocarbamate (SBEC), sodium diethyldithiocarbamate (SDEC), tellurium diethyldithiocarbamate (TDEC), and zinc dibenzyldithiocarbamate (ZEBC).

[0308] As used herein, the term "activator" refers to any substance that activates the vulcanizing agent and crosslinks the elastomer as described above. The activator can function by various mechanisms, including but not limited to by forming a chemical complex with an accelerator or by coordinating with sulfur (when sulfur is used as a vulcanizing agent). Non-limiting examples of activators include metal oxides, acids, and metal complexes. Non-limiting examples of metal oxides include zinc oxide, magnesium oxide, and lead oxide. Non-limiting examples of acids include stearic acid and lauric acid. Non-limiting examples of metal complexes include zinc ethylhexanoate.

[0309] As used herein, the term "pre-vulcanization inhibitor" refers to a compound that delays the onset of vulcanization and / or the rate of vulcanization. These compounds are also referred to as "retarders". Non-limiting examples of pre-vulcanization inhibitors include N-(cyclohexylthio)phthalimide (CTP), benzoic anhydride, salicylic anhydride, and phthalic anhydride.

[0310] In some embodiments, the compositions of the present disclosure include about 15 wt / wt% to about 85 wt / wt% of one or more rubber chemicals. In some embodiments, the compositions include about 1 wt / wt% to about 5 wt / wt%, about 1 wt / wt% to about 15 wt / wt%, about 1 wt / wt% to about 25 wt / wt%, about 1 wt / wt% to about 35 wt / wt%, about 1 wt / wt% to about 45 wt / wt%, about 1 wt / wt% to about 55 wt / wt%, about 1 wt / wt% to about 65 wt / wt%, about 1 wt / wt% to about 75 wt / wt%, about 1 wt / wt% to about 85 wt / wt%, about 1 wt / wt% to about 95 wt / wt%, about 5 wt / wt% to about 15 wt / wt%, about 5 wt / wt% to about %, about 5 wt / wt% to about 65 wt / wt%, about 5 wt / wt% to about 75 wt / wt%, about 5 wt / wt% to about 85 wt / wt%, about 5 wt / wt% to about 95 wt / wt%, about 15 wt / wt% to about 25 wt / wt%, about 15 wt / wt% to about 35 wt / wt%, about 15 wt / wt% to about 45 wt / wt%, about 15 wt / wt% to about 55 wt / wt%, about 15 wt / wt% to about 65 wt / wt%, about 5 wt / wt% to about 75 wt / wt%, about 5 wt / wt% to about 85 wt / wt%, about 5 wt / wt% to about 95 wt / wt%, about 15 wt / wt% to about 25 wt / wt%, about 15 wt / wt% to about 35 wt / wt%, about 15 wt / wt% to about 45 wt / wt%, about 15 wt / wt% to about 55 wt / wt%, about 15 wt / wt% to about %, about 15 wt / wt% to about 75 wt / wt%, about 15 wt / wt% to about 95 wt / wt%, about 25 wt / wt% to about 35 wt / wt%, about 25 wt / wt% to about 45 wt / wt%, about 25 wt / wt% to about 55 wt / wt%, about 25 wt / wt% to about 65 wt / wt%, about 25 wt / wt% to about 75 wt / wt%, about 25 wt / wt% to about 85 wt / wt%, about 25 wt / wt% to about 95 wt / wt%, about 35 wt / wt% to about 45 wt / wt%, about 35 wt / wt% to about 55 wt / wt%, about 35 wt / wt% to about 65 wt / wt%, about 25 wt / wt% to about 75 wt / wt%, about 25 wt / wt% to about 85 wt / wt%, about 25 wt / wt% to about 95 wt / wt%, about 35 wt / wt% to about 45 wt / wt%, about 35 wt / wt% to about 55 wt / wt%, about 35 wt / wt% to about % to about 65 wt / wt%, about 35 wt / wt% to about 75 wt / wt%, about 35 wt / wt% to about 85 wt / wt%, about 35 wt / wt% to about 95 wt / wt%, about 45 wt / wt% to about 55 wt / wt%, about 45 wt / wt% to about 65 wt / wt%, about 45 wt / wt% to about 75 wt / wt%, about 45 wt / wt% to about 85 wt / wt%, about 45 wt / wt% to about 95 wt / wt%, about 55 wt / wt% to about 65 wt / wt%, about 55 wt / wt% to about 75 wt / wt%, about 55 wt / wt% to about 85 wt / wt%,About 55 wt / wt% to about 95 wt / wt%, about 65 wt / wt% to about 75 wt / wt%, about 65 wt / wt% to about 85 wt / wt%, about 65 wt / wt% to about 95 wt / wt%, about 75 wt / wt% to about 85 wt / wt%, about 75 wt / wt% to about 95 wt / wt%, or about 85 wt / wt% to about 95 wt / wt% of one or more rubber chemicals.

[0311] In some embodiments, the composition of the present disclosure includes one or more rubber chemicals of about 15 wt / wt%. In some embodiments, the composition includes one or more rubber chemicals 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%.

[0312] In some embodiments, the compositions of the present disclosure include from about 1 phr to about 20 phr of one or more rubber chemicals. In some embodiments, the composition comprises from about 0.1 phr to about 1 phr, from about 0.1 phr to about 5 phr, from about 0.1 phr to about 10 phr, from about 0.1 phr to about 15 phr, from about 0.1 phr to about 20 phr, from about 0.1 phr to about 25 phr, from about 0.1 phr to about 30 phr, from about 0.1 phr to about 35 phr, from about 0.1 phr to about 40 phr, from about 1 phr to about 5 phr, from about 1 phr to about 10 phr, from about 1 phr to about 15 phr, from about 1 phr to about 25 phr, from about 1 phr to about 30 phr, from about 1 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 One or more rubber chemicals may be present in an amount of about 20 phr to about 25 phr, about 20 phr to about 30 phr, about 20 phr to about 35 phr, about 20 phr to about 40 phr, about 25 phr to about 30 phr, about 25 phr to about 35 phr, about 25 phr to about 40 phr, about 30 phr to about 35 phr, about 30 phr to about 40 phr, or about 35 phr to about 40 phr.

[0313] In some embodiments, the composition of the present disclosure comprises about 10 phr of one or more rubber chemicals. In some embodiments, the composition comprises about 0.1 phr, about 1 phr, about 5 phr, about 15 phr, about 20 phr, about 25 phr, about 30 phr, about 35 phr, or about 40 phr of one or more rubber chemicals.

[0314] As used herein, the term "plasticizer" refers to a processing aid for reducing viscosity, increasing plasticity and / or expanding the volume of the composition. The plasticizer helps to mix and form the process of the composition comprising the elastomer before the vulcanization composition. Non-limiting examples of plasticizers include mineral oils (paraffin oil, aromatic oil or naphthenic oil), organic esters, resins, waxes, ester plasticizers and oils of natural origin, such as soybean oil, vegetable oil or orange oil.

[0315] In some embodiments, the compositions of the present disclosure comprise from about 15 wt / wt% to about 85 wt / wt% of one or more plasticizers. In some embodiments, the compositions comprise 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 %, about 5 wt / wt% to about 65 wt / wt%, about 5 wt / wt% to about 75 wt / wt%, about 5 wt / wt% to about 85 wt / wt%, about 5 wt / wt% to about 95 wt / wt%, about 15 wt / wt% to about 25 wt / wt%, about 15 wt / wt% to about 35 wt / wt%, about 15 wt / wt% to about 45 wt / wt%, about 15 wt / wt% to about 55 wt / wt%, about 15 wt / wt% to about 65 wt / wt%, about 5 wt / wt% to about 75 wt / wt%, about 5 wt / wt% to about 85 wt / wt%, about 5 wt / wt% to about 95 wt / wt%, about 15 wt / wt% to about 25 wt / wt%, about 15 wt / wt% to about 35 wt / wt%, about 15 wt / wt% to about 45 wt / wt%, about 15 wt / wt% to about 55 wt / wt%, about 15 wt / wt% to about %, about 15 wt / wt% to about 75 wt / wt%, about 15 wt / wt% to about 95 wt / wt%, about 25 wt / wt% to about 35 wt / wt%, about 25 wt / wt% to about 45 wt / wt%, about 25 wt / wt% to about 55 wt / wt%, about 25 wt / wt% to about 65 wt / wt%, about 25 wt / wt% to about 75 wt / wt%, about 25 wt / wt% to about 85 wt / wt%, about 25 wt / wt% to about 95 wt / wt%, about 35 wt / wt% to about 45 wt / wt%, about 35 wt / wt% to about 55 wt / wt%, about 35 wt / wt% to about 65 wt / wt%, about 25 wt / wt% to about 75 wt / wt%, about 25 wt / wt% to about 85 wt / wt%, about 25 wt / wt% to about 95 wt / wt%, about 35 wt / wt% to about 45 wt / wt%, about 35 wt / wt% to about 55 wt / wt%, about 35 wt / wt% to about % to about 65 wt / wt%, about 35 wt / wt% to about 75 wt / wt%, about 35 wt / wt% to about 85 wt / wt%, about 35 wt / wt% to about 95 wt / wt%, about 45 wt / wt% to about 55 wt / wt%, about 45 wt / wt% to about 65 wt / wt%, about 45 wt / wt% to about 75 wt / wt%, about 45 wt / wt% to about 85 wt / wt%, about 45 wt / wt% to about 95 wt / wt%, about 55 wt / wt% to about 65 wt / wt%, about 55 wt / wt% to about 75 wt / wt%, about 55 wt / wt% to about 85 wt / wt%,About 55 wt / wt% to about 95 wt / wt%, about 65 wt / wt% to about 75 wt / wt%, about 65 wt / wt% to about 85 wt / wt%, about 65 wt / wt% to about 95 wt / wt%, about 75 wt / wt% to about 85 wt / wt%, about 75 wt / wt% to about 95 wt / wt%, or about 85 wt / wt% to about 95 wt / wt% of one or more plasticizers.

[0316] In some embodiments, the composition of the present disclosure comprises about 15 wt / wt% of one or more plasticizers. In some embodiments, the composition comprises about 1 wt / wt%, about 5 wt / wt%, about 10 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt% or about 95 wt / wt% of one or more plasticizers.

[0317] In some embodiments, the compositions of the present disclosure include from about 1 phr to about 20 phr of one or more plasticizers. In some embodiments, the composition comprises from about 0.1 phr to about 1 phr, from about 0.1 phr to about 5 phr, from about 0.1 phr to about 10 phr, from about 0.1 phr to about 15 phr, from about 0.1 phr to about 20 phr, from about 0.1 phr to about 25 phr, from about 0.1 phr to about 30 phr, from about 0.1 phr to about 35 phr, from about 0.1 phr to about 40 phr, from about 1 phr to about 5 phr, from about 1 phr to about 10 phr, from about 1 phr to about 15 phr, from about 1 phr to about 25 phr, from about 1 phr to about 30 phr, from about 1 phr to about 35 phr, from about 1 phr to about 40 phr, from about 5 phr to about 10 phr, from about 5 phr to about 15 phr, from about 5 phr to about 20 phr, from about 5 phr to about 25 phr, from about 5 phr to about 30 phr, from about 5 phr to about 35 phr, from about 5 phr to about 40 phr, from about 10 phr to about 15 phr, from about 10 phr to about 20 phr, from about 10 phr to about 25 phr, from about 10 phr to about 30 phr, from about 10 phr to about 35 phr, from about 10 phr to about 40 phr, from about 15 phr to about 20 phr, from about 15 phr to about 25 phr, from about 15 phr to about 30 phr, from about 15 phr to about 35 phr, from about 15 phr to about 40 phr, from about 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 phr to about 40 phr, about 20 phr to about 25 phr, about 20 phr to about 30 phr, about 20 phr to about 35 phr, about 20 phr to about 40 phr, about 25 phr to about 30 phr, about 25 phr to about 35 phr, about 25 phr to about 40 phr, about 30 phr to about 35 phr, about 30 phr to about 40 phr, or about 35 phr to about 40 phr of one or more plasticizers.

[0318] In some embodiments, the compositions of the present disclosure include about 10 phr of one or more plasticizers. In some embodiments, the compositions include about 0.1 phr, about 1 phr, about 5 phr, about 15 phr, about 20 phr, about 25 phr, about 30 phr, about 35 phr, or about 40 phr of one or more plasticizers.

[0319] In some embodiments, the compositions of the present disclosure further comprise a second antidegradant that is not a compound of the present disclosure. In some embodiments, the second antidegradant is an antioxidant. In some embodiments, the second antidegradant is an antiozonant. Non-limiting examples of antidegradants include p-phenylenediamine (PPD), trimethyl-dihydroquinoline (TMQ), phenols, alkylated diphenylamine (DPA), diphenylamine-ketone condensates, and natural antidegradants. 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 oligomers or polymers thereof.

[0320] In some embodiments, the compositions of the present disclosure comprise about 15 wt / wt% to about 85 wt / wt% of the second antidegradant. In some embodiments, the composition comprises about 1 wt / wt% to about 5 wt / wt%, about 1 wt / wt% to about 15 wt / wt%, about 1 wt / wt% to about 25 wt / wt%, about 1 wt / wt% to about 35 wt / wt%, about 1 wt / wt% to about 45 wt / wt%, about 1 wt / wt% to about 55 wt / wt%, about 1 wt / wt% to about 65 wt / wt%, about 1 wt / wt% to about 75 wt / wt%, about 1 wt / wt% to about 85 wt / wt%, about 1 wt / wt% to about 95 wt / wt%, about 5 wt / wt% to about 15 wt / wt%, about 5 ... %, about 5 wt / wt% to about 35 wt / wt%, about 5 wt / wt% to about 45 wt / wt%, about 5 wt / wt% to about 55 wt / wt%, about 5 wt / wt% to about 65 wt / wt%, about 5 wt / wt% to about 75 wt / wt%, about 5 wt / wt% to about 85 wt / wt%, about 5 wt / wt% to about 95 wt / wt%, about 15 wt / wt% to about 25 wt / wt%, about 15 wt / wt% to about 35 wt / wt%, about 15 wt / wt% to about 45 wt / wt%, about 15 wt / wt% to about 55 wt / wt%, about 15 wt / wt% to about 65 wt / wt%, about 1 %, about 25 wt / wt% to about 75 wt / wt%, about 15 wt / wt% to about 95 wt / wt%, about 25 wt / wt% to about 35 wt / wt%, about 25 wt / wt% to about 45 wt / wt%, about 25 wt / wt% to about 55 wt / wt%, about 25 wt / wt% to about 65 wt / wt%, about 25 wt / wt% to about 75 wt / wt%, about 25 wt / wt% to about 85 wt / wt%, about 25 wt / wt% to about 95 wt / wt%, about 35 wt / wt% to about 45 wt / wt%, about 35 wt / wt% to about 55 wt / wt%, about 35 wt / wt% to about 65 wt / wt%, about %, about 35 wt / wt% to about 75 wt / wt%, about 35 wt / wt% to about 85 wt / wt%, about 35 wt / wt% to about 95 wt / wt%, about 45 wt / wt% to about 55 wt / wt%, about 45 wt / wt% to about 65 wt / wt%, about 45 wt / wt% to about 75 wt / wt%, about 45 wt / wt% to about 85 wt / wt%, about 45 wt / wt% to about 95 wt / wt%, about 55 wt / wt% to about 65 wt / wt%, about 55 wt / wt% to about 75 wt / wt%, about 55 wt / wt% to about 85 wt / wt%, about 55 wt / wt% to about 95 wt / wt%,About 65 wt / wt% to about 75 wt / wt%, about 65 wt / wt% to about 85 wt / wt%, about 65 wt / wt% to about 95 wt / wt%, about 75 wt / wt% to about 85 wt / wt%, about 75 wt / wt% to about 95 wt / wt%, or about 85 wt / wt% to about 95 wt / wt% of the second antidegradant.

[0321] In some embodiments, the compositions of the present disclosure comprise about 15 wt / wt% of the second antidegradant. In some embodiments, the compositions comprise about 1 wt / wt%, about 5 wt / wt%, about 10 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt% of the second antidegradant.

[0322] In some embodiments, the compositions of the present disclosure comprise from about 1 phr to about 5 phr of a second antidegradant. In some embodiments, the compositions comprise from about 0.001 phr to about 0.01 phr, from about 0.001 phr to about 0.1 phr, from about 0.001 phr to about 1 phr, from about 0.001 phr to about 5 phr, from about 0.001 phr to about 7.5 phr, from about 0.001 phr to about 10 phr, from about 0.01 phr to about 0.1 phr, from about 0.01 phr to about 1 phr, from about 0.01 phr to about 5 phr, hr, 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.

[0323] In some embodiments, the compositions of the present disclosure comprise about 3 phr of a second antidegradant. In some embodiments, the compositions comprise 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 a second antidegradant.

[0324] In some embodiments, the present disclosure provides a composition comprising a compound of the present disclosure and one or more carriers. As used herein, the term "carrier" refers to a solid capable of adsorbing 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.

[0325] In some embodiments, the composition comprises about 15% to about 85% w / w of one or more carriers. In some embodiments, the composition comprises about 1% to about 5% w / w, about 1% to about 15% w / w, about 1% to about 25% w / w, about 1% to about 35% w / w, about 1% to about 45% w / w, about 1% to about 55% w / w, about 1% to about 65% w / w, about 1% to about 75% w / w, about 1% to about 85% w / w, about 1% to about 95% w / w, about 5% to about 15% w / w, about 5% to about 25% w / w %, about 5 wt / wt% to about 35 wt / wt%, about 5 wt / wt% to about 45 wt / wt%, about 5 wt / wt% to about 55 wt / wt%, about 5 wt / wt% to about 65 wt / wt%, about 5 wt / wt% to about 75 wt / wt%, about 5 wt / wt% to about 85 wt / wt%, about 5 wt / wt% to about 95 wt / wt%, about 15 wt / wt% to about 25 wt / wt%, about 15 wt / wt% to about 35 wt / wt%, about 15 wt / wt% to about 45 wt / wt%, about 15 wt / wt% to about 55 wt / wt%, about 15 wt / wt% to about 65 wt / wt%, about 1 %, about 25 wt / wt% to about 75 wt / wt%, about 15 wt / wt% to about 95 wt / wt%, about 25 wt / wt% to about 35 wt / wt%, about 25 wt / wt% to about 45 wt / wt%, about 25 wt / wt% to about 55 wt / wt%, about 25 wt / wt% to about 65 wt / wt%, about 25 wt / wt% to about 75 wt / wt%, about 25 wt / wt% to about 85 wt / wt%, about 25 wt / wt% to about 95 wt / wt%, about 35 wt / wt% to about 45 wt / wt%, about 35 wt / wt% to about 55 wt / wt%, about 35 wt / wt% to about 65 wt / wt%, about %, about 35 wt / wt% to about 75 wt / wt%, about 35 wt / wt% to about 85 wt / wt%, about 35 wt / wt% to about 95 wt / wt%, about 45 wt / wt% to about 55 wt / wt%, about 45 wt / wt% to about 65 wt / wt%, about 45 wt / wt% to about 75 wt / wt%, about 45 wt / wt% to about 85 wt / wt%, about 45 wt / wt% to about 95 wt / wt%, about 55 wt / wt% to about 65 wt / wt%, about 55 wt / wt% to about 75 wt / wt%, about 55 wt / wt% to about 85 wt / wt%, about 55 wt / wt% to about 95 wt / wt%,About 65% to about 75% w / w, about 65% to about 85% w / w, about 65% to about 95% w / w, about 75% to about 85% w / w, about 75% to about 95% w / w, or about 85% to about 95% w / w of one or more carriers.

[0326] In some embodiments, the composition comprises about 15 wt / wt% of one or more carriers. In some embodiments, the composition comprises about 1 wt / wt%, about 5 wt / wt%, about 10 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt% or about 95 wt / wt% of one or more carriers.

[0327] The present disclosure also provides a method for preparing a composition comprising a compound of the present disclosure and one or more carriers, the method comprising mixing the compound with the one or more carriers.

[0328] The present disclosure also provides lubricant compositions comprising compounds of the present disclosure and lubricants. Non-limiting examples of lubricants include mineral oils, higher molecular weight petroleum fractions (such as aromatic, naphthenic and paraffinic fractions), synthetic oils (such as poly-alpha-olefins (PAO)), synthetic esters, polyalkylene glycols (PAGs), phosphate esters, perfluoropolyethers (PFPEs), alkylated naphthalenes (ANs), silicates, ionic fluids and polyalkylated cyclopentanes (MACs), solid lubricants (such as polytetrafluoroethylene (PTFE), graphite, hexagonal boron nitride, molybdenum disulfide, tungsten disulfide), aqueous lubricants (such as hydrated brush polymers) and biolubricants (such as triglycerides, high oleic rapeseed oil, castor oil, palm oil, sunflower oil and rapeseed oil).

[0329] The present disclosure also provides a combustible fuel composition comprising a combustible fuel and a compound of the present disclosure.Non-limiting examples of combustible fuels include gasoline, diesel, kerosene, liquefied petroleum gas, synthetic fuels, and biodiesel.

[0330] The present disclosure also provides a fuel additive composition comprising a fuel additive and a compound of the present disclosure. The non-limiting examples of fuel additives include oxygenates (such as alcohols and ethers), antioxidants, stabilizers, detergents, antiknock agents, lead scavengers, fuel dyes, viscosity improvers and butyl rubber. In some embodiments, butyl rubber is in the form of polyisobutylene succinimide. In some embodiments, butyl rubber is added as a detergent to prevent diesel injector fouling.

[0331] Vulcanized elastomer products

[0332] The present disclosure also provides vulcanized elastomeric articles comprising the compounds of the present disclosure.The term "vulcanized elastomeric 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.

[0333] The present disclosure also provides vulcanized elastomeric articles prepared using the compositions described herein.

[0334] In some embodiments, the vulcanized elastomeric article is a tire. In some embodiments, the tire is a passenger car tire, a light truck tire, a heavy truck or bus tire, a motorcycle tire, an agricultural tire, a bulldozer tire, an aircraft tire, or a racing tire.

[0335] In some embodiments, the vulcanized elastomeric article is a component of a tire. In some embodiments, the component is a bead, a belt, a carcass ply, an inner liner, a sidewall, a base tread, or a tread.

[0336] In some embodiments, the vulcanized elastomeric article is a rubber overshoe, weatherstrip, soundproofing panel, air spring, bellows, membrane, tactile sensor, anti-vibration pad, hose, conveyor belt, or flooring.

[0337] method

[0338] The present disclosure also provides a method for preparing a vulcanized elastomeric article, the method comprising:

[0339] (a) forming a composition as described herein into a shaped shape; and

[0340] (b) vulcanizing the formed shape,

[0341] To provide a vulcanized elastomeric product.

[0342] In some embodiments, vulcanization is carried out at an average temperature of about 140° C. to about 160° C. In some embodiments, 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.

[0343] In some embodiments, vulcanization is performed at an average temperature of about 150° C. In some embodiments, vulcanization is performed at an average temperature of about 80° C., about 100° C., about 120° C., about 140° C., about 160° C., about 180° C., or about 200° C.

[0344] The present disclosure also provides a method for retreading a tire, the method comprising:

[0345] (a) applying a composition as described herein to a tire;

[0346] (b) providing a pre-cured tread around the tire;

[0347] (c) providing a curing envelope around the tire; and

[0348] (d) vulcanizing the tire.

[0349] Reagent test kit

[0350] The present disclosure also provides a kit comprising a composition as described herein, which is packaged in a manner such as a container, thereby facilitating the use of the composition to practice the process and / or method of the present disclosure. In some embodiments, the kit includes a composition as described herein and instructions for using the composition in a vulcanizable elastomer composition. In some embodiments, the kit includes a composition as described herein and instructions for preparing a vulcanized elastomer article using the composition. The composition can be packaged in any suitable container, such as a sealed bottle or vessel, and a label is attached to the container or included in the kit, the label describing the composition and its correct use.

[0351] The present disclosure also provides the following specific embodiments.

[0352] Embodiment 1. A compound having formula (I):

[0353]

[0354] or a salt or solvate thereof, wherein:

[0355] R 1 Selected from the group consisting of: C1-C 12 Alkyl, -CHR 1a R 1b , C3-C6 cycloalkyl, and optionally substituted phenyl; or

[0356] R 1 and R 4 Together with the nitrogen atom and the carbon atom to which they are attached, they form a saturated or partially saturated optionally substituted 5- or 6-membered heterocyclic ring;

[0357] R 1a Selected from the group consisting of optionally substituted phenyl, C3-C6 cycloalkyl and optionally substituted 5 or 6 membered heteroaryl;

[0358] R 1b Selected from the group consisting of hydrogen C1-C6 alkyl;

[0359] R 2 Selected from the group consisting of: C1-C 12 Alkyl, -CHR 2a R 2b , C3-C6 cycloalkyl, and optionally substituted phenyl; or

[0360] R 2 and R 8 Together with the nitrogen atom and the carbon atom to which they are attached, they form a saturated or partially saturated optionally substituted 5- or 6-membered heterocyclic ring;

[0361] R 2a Selected from the group consisting of optionally substituted phenyl, C3-C6 cycloalkyl and optionally substituted 5 or 6 membered heteroaryl;

[0362] R 2b Selected from the group consisting of hydrogen and C1-C6 alkyl;

[0363] X-Select Free-CHR 3a -、-NR 3b -, -O-, and -S-;

[0364] R 3a 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;

[0365] R 3bSelected from the group consisting of: 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;

[0366] R 4 , R 5 , R 6 and R 7 independently selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy and C1-C6 alkylthio; or

[0367] R 1 and R 4 Together with the nitrogen atom and the carbon atom to which they are attached, they form a saturated or partially saturated optionally substituted 5- or 6-membered heterocyclic ring; and

[0368] 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; and

[0369] R 8 , R 9 , R 10 and R 11 independently selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy and C1-C6 alkylthio; or

[0370] R 2 and R 8 Together with the nitrogen atom and the carbon atom to which they are attached, they form a saturated or partially saturated optionally substituted 5- or 6-membered heterocyclic ring; and

[0371] R 9 , R 10 and R 11 independently selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy and C1-C6 alkylthio,

[0372] Provided that: (i) if X is O- or -S-, then R 1 Selected from the group consisting of: methyl, ethyl, pentyl, hexyl, heptyl, nonyl, decyl, undecyl, dodecyl, -CHR 1a R 1b , C3-C6 cycloalkyl, and optionally substituted phenyl; or

[0373] R 1 and R 4Together with the nitrogen atom and the carbon atom to which they are attached, they form a saturated or partially saturated optionally substituted 5- or 6-membered heterocyclic ring; and

[0374] R 2 Selected from the group consisting of: methyl, ethyl, pentyl, hexyl, heptyl, nonyl, decyl, undecyl, dodecyl, -CHR 2a R 2b , C3-C6 cycloalkyl, and optionally substituted phenyl; or

[0375] R 2 and R 8 Together with the nitrogen atom and the carbon atom to which they are attached, they form a saturated or partially saturated optionally substituted 5- or 6-membered heterocyclic ring; and

[0376] (ii) If X is -CHCH3-, then R 1 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

[0377] R 1 and R 4 Together with the nitrogen atom and the carbon atom to which they are attached, they form a saturated or partially saturated optionally substituted 5- or 6-membered heterocyclic ring; and

[0378] R 2 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

[0379] R 2 and R 8 Together with the nitrogen atom and the carbon atom to which they are attached, they respectively form a saturated or partially saturated optionally substituted 5- or 6-membered heterocyclic ring.

[0380] Embodiment II. Compounds of Embodiment I, wherein X is -CHR 3a -.

[0381] Embodiment III. Compounds of Embodiment I or II, wherein R 3a 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.

[0382] Embodiment IV. Compounds of Embodiment III, wherein R 3ayes:

[0383]

[0384] Embodiment V. Compounds of Embodiment I, wherein X is -NH-.

[0385] Embodiment VI. The compound of Embodiment I, wherein X is -O-.

[0386] Embodiment VII. Compounds of Embodiment I wherein X is -S-.

[0387] Embodiment VIII. Compounds of any one of Embodiments I-VII, wherein R 1 It is C1-C 12 Alkyl or -CHR 1a R 1b and R 2 It is C1-C 12 Alkyl or -CHR 2a R 2b .

[0388] Embodiment IX. Compounds of Embodiment VIII, wherein R 1a and R 2a yes:

[0389] and

[0390] R 1b and R 2b It's hydrogen.

[0391] Embodiment X. Compounds of Embodiment VIII, wherein R 1 and R 2 It is isopropyl.

[0392] Embodiment XI. A composition comprising:

[0393] (i) a compound according to any one of Embodiments IX; and

[0394] (ii) one or more elastomers; or

[0395] (iii) one or more fillers; or

[0396] (iv) one or more rubber chemicals; or

[0397] (v) one or more plasticizers; or

[0398] (vi) a second antidegradant; or

[0399] (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 antidegradant.

[0400] Example

[0401] Example 1

[0402] Synthesis of Bis(2,2,4-trimethyl-1,2-dihydroquinolin-6-yl)methane (Compound 1)

[0403]

[0404] A 100 mL flask equipped with a stirring bar and a thermometer was charged with 4,4'-methylenedianiline (0.918 g; 4.63 mmol) and acetone (3.5 mL). The mixture was stirred under N2 protection. Zinc (II) trifluoromethanesulfonate (0.1755 g; 4.83 mmol) was added in one portion. The reaction mixture was stirred at room temperature for 6-7 days. The resulting dark slurry was loaded onto a chromatographic column (2.4 cm inner diameter) previously prepared with silica gel 60 (70-230 mesh) and eluent (20% ethyl acetate in hexane). The fraction at Rf = 0.8 was collected and the volatiles were removed under reduced pressure (rotary evaporator; water bath = 50 °C). The resulting solid was dried on a rotary evaporator (50 °C; <5 mbar) for 1 hour. The product was a light yellow solid weighing 0.41 g (yield 25%). Representative 1 H and 13 CNMR spectra Figure 1(a) and 1(b) shown.

[0405] Example 2

[0406] Synthesis of Bis(2,2,4-Trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)methane (Compound 2)

[0407]

[0408] 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 nitrogen. 50 PSI H2 was charged into the vessel and the reaction mixture was stirred at 25°C for 1 hour. After the reaction was complete, the reactants were filtered through a 0.5 μm frit to separate the catalyst residue from the product. The volatiles in the filtrate were removed under reduced pressure (rotary evaporator; water bath = 50°C). The crude hydrogenated material was dissolved in chloroform as the dihydrochloride salt. The emerald green solution was transferred to a separatory funnel, washed with saturated aqueous NaHCO3, dried over anhydrous MgSO4, filtered, and the volatiles were removed under reduced pressure (rotary evaporator; water bath = 50°C). Further drying until constant weight gave the desired product as a green-yellow viscous liquid. Representative 1 H and 13 C NMR spectroscopy Figure 2(a) and 2(b) shown.

[0409] Example 3

[0410] Synthesis of 4,4'-(furan-2-ylmethylene)bis(N-isopropylaniline) (Compound 3)

[0411]

[0412] A 25 mL round-bottom flask equipped with a stirring bar and a reflux condenser was charged with N-isopropylaniline (7.0 mL; 48.7 mmol), furfural (1.6 mL; 19.3 mmol), and ytterbium (III) trifluoromethanesulfonate hydrate (1.15 g; <1.85 mmol Yb 3+). The reaction mixture was stirred and heated (oil bath temperature = 95°C) for 17 hours under N2 protection. When cooled to room temperature, the obtained dark material was dissolved in ethyl acetate (about 100 mL). The obtained dark solution was washed with 0.5M NaOH aqueous solution (20 mL), 1M NaHCO3 aqueous solution (20 mL), distilled water (20 mL) and saturated NaCl aqueous solution (20 mL). Most of the volatile substances in the organic phase were removed. The obtained dark solution was loaded onto a 41 mm inner diameter column chromatography prepared in advance with silica gel 60 (15-16 cm high) and eluent (10% ethyl acetate in hexane). The column was eluted with 10% AcOEt in hexane. Several fractions (80 mL each) were collected. Each fraction was characterized by TLC (10% AcOEt in hexane). The fractions containing points at Rf = 0.6 (per-N-isopropylaniline), 0.4 (unknown impurity; trace) and 0.5 (unknown impurity; trace) were discarded. The fractions containing the spot at Rf = 0.3 (compound 3) were collected and the volatiles were removed under reduced pressure (rotavapor; water bath = 60°C). The resulting light brown viscous liquid was dried on a rotary evaporator (60°C; <5 mbar) for 10 min. Yield = 1.4 g (21% based on furfural), very viscous brown liquid. Representative 1 H and 13 C NMR spectroscopy Figure 3(a) and 3(b) shown.

[0413] Example 4

[0414] Synthesis of 4,4'-(furan-2-ylmethylene)bis(N-(furan-2-ylmethyl)aniline) (Compound 7)

[0415]

[0416] By N, N-dibenzyl aniline (42.58g, 156.120mmol, 2.14 equivalents), furfural (7.00g, 72.9mmol, 1.0 equivalents) and p-toluenesulfonic acid monohydrate (9.89g, 51.982mmol, 0.7 equivalents) solution in toluene (100mL) was heated overnight at 110 DEG C. The reaction was cooled to room temperature and diluted with dichloromethane (300mL). The mixture was washed with saturated sodium bicarbonate (100mL), and the organic layer was concentrated under reduced pressure. The residue was dry loaded onto silica (70g) and purified on Interchim automatic chromatography system (2x 350g stacked pre-filled 20mm silica column), with the gradient elution of 0 to 20% ethyl acetate in heptane, to obtain intermediate compound 7-I (19.9g, 44% yield) as a white solid.

[0417] Compound 7-I (47.0g, 75.22mmol, 1.0 equivalent) and 5% palladium carbon (2.35g, 50% water moistening) in 1: 1 methanol (235mL) and THF (235mL, 5 volumes) suspension in mixture was hydrogenated at 25psi for 2 hours. After completion, reactant was filtered through diatomite (30g), and washed with methanol (200mL). The filtrate was concentrated under reduced pressure. The residue was dry loaded onto silica gel (50g) and purified on Interchim automatic chromatography system (220g, pre-filled 60mm silica column), eluted with a gradient of 25 to 100% ethyl acetate in heptane, compound 7-II (13.7g, 69% yield) was obtained as off-white solid and 4,4'-((tetrahydrofuran-2-yl) methylene) diphenylamine (2.1g, 10% yield) was off-white solid.

[0418] A solution of compound 7-II (13.7 g, 51.83 mmol, 1.0 equivalent) and furfural (9.96 g, 103.66 mmol, 2.0 equivalent) in dichloromethane (360 mL, 36 volumes) was stirred for 1 hour. Sodium triacetoxyborohydride (30.76 g, 145.123 mmol, 2.8 equivalents) was added at room temperature, and the reaction was stirred for one hour. LCMS and NMR analysis showed that the reaction was complete. 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 (2×130 mL). The combined organic matter was 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 automatic chromatography system (250 g, pre-filled 60 μm silica column), eluted with a gradient of 0 to 30% ethyl acetate in heptane. The fractions containing the pure product were then concentrated under reduced pressure and dried at 50 °C under high vacuum overnight to afford compound 7 (18.3 g, 83% yield, >95% HPLC purity) as an off-white oil. 1 HNMR (400MHz, DMSO-d6) δ = 7.58–7.51 (m, 3H), 6.86 (d, J = 8.6Hz, 4H), 6.66–6.50 (m, 4H), 6.40–6.33 (m, 3H), 6.28 (dd, J = 0.7, 3.2Hz, 2H), 6.01–5.86 (m, 3H), 5.19–5.12 (m, 1H), 4.20 (d, J = 6.0Hz, 4H); 13C (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] for C27H24N2O3 + The calculated value is 425.2 and the measured value is 425.2.

[0419] Example 5

[0420] Synthesis of 4,4'-methylenebis(N-(furan-2-ylmethyl)aniline)(Compound 8)

[0421]

[0422] Furfural (8.80mL, 106mmol, 2.1 equivalents) and sodium sulfate (14.3g, 101mmol, 2.0 equivalents) are added to a solution of 4,4'-methylenedianiline (10.0g, 50.4mmol, 1.0 equivalents) in methanol (100mL) in a three-neck 500mL round-bottom flask. The reaction is stirred at room temperature for 1 hour. Sodium borohydride (4.00g, 101mmol, 2.1 equivalents) is added in batches within 15 minutes (note the exothermic, methanol begins to reflux). The reaction is vigorously stirred at room temperature for 1 hour. The mixture is transferred to a single-necked round bottom containing methanol and concentrated under reduced pressure. The residue is quenched with water (200mL) and diluted with ethyl acetate (400mL). Separate the layers and extract the aqueous layer with ethyl acetate (2x 200mL). The combined organic matter is dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was absorbed onto silica gel (40 g) using dichloromethane (loading with ethyl acetate would cause solubility problems during purification) and purified on a Biotage automated chromatography system (350 g, Biotage 60 μm silica gel column) eluting with a gradient of 0 to 30% ethyl acetate in hexane. The resulting solid was dried under vacuum at room temperature for 18 hours to give compound 8 (13.9 g, 77% yield, >95% HPLC purity) as an off-white solid. 1 H NMR (400MHz, CDCl3) δ = 7.34 (dd, J = 0.8, 1.8Hz, 2H), 7.00–6.96 (m, 4H), 6.60–6.56 (m , 4H), 6.30 (dd, J=1.8, 3.2Hz, 2H), 6.20 (dd, J=0.7, 3.2Hz, 2H), 4.26 (s, 4H), 3.89 (br s,2H),3.76(s,2H); 13C NMR(101MHz, CDCl3)d=152.97(s,2C),145.81,141.91(s,2C),131.54(s,2C),129 .62(s,2C),113.33(s,4C),110.36(s,2C),106.95(s,2C),41.74(s,2C),40.17;C 23 H 22 MS (ESI) m / z[M+H] of N2O2 + The calculated value is 359.2 and the measured value is 359.1.

[0423] Example 6

[0424] Synthesis of 4,4'-(phenylmethylene)bis(N-isopropylaniline) (Compound 16)

[0425]

[0426] N,N-diisopropylethylamine (155mL, 888mmol, 1.5 equiv) was added to a solution of N-isopropylaniline (80g, 592mmol, 1 equiv) and benzyl bromide (121.5g, 711mmol, 1.2 equiv) in N,N-dimethylacetamide (700mL). The mixture was stirred at 110°C for 2 hours, at which time LC / MS analysis indicated that the reaction was complete. After cooling to room temperature, the mixture was diluted with saturated brine (1.5L) and extracted with ethyl acetate (3×1L). The combined organic layers were washed with saturated brine (1L), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified over silica gel (1.2kg) eluted with a gradient of 5% to 10% dichloromethane in heptane to give compound 8-I (114g, 86% yield,>94% HPLC purity) as a colorless oil.

[0427] Toluenesulfonic acid monohydrate (32.6 g, 171.4 mmol, 0.6 equivalent) is added to a solution of compound 8-I (64 g, 285.7 mmol, 1 equivalent) and benzaldehyde (18.2 g, 171.4 mmol, 0.6 equivalent) in toluene (500 mL). The reaction mixture is refluxed, equipped with a Dean-Stark apparatus, for 24 hours, at which time LC / MS analysis shows that the conversion rate of compound 8-I to compound 8-II is 65%. After cooling to room temperature, most of the toluene is removed under reduced pressure. The residue is diluted with ethyl acetate (1.5 L). The resulting mixture is washed with saturated sodium bicarbonate (2 × 1 L) and saturated brine (2 × 1 L) in turn. The organic layer is dried over sodium sulfate, filtered and concentrated under reduced pressure to remove three-quarters of the solvent. The residual solution is added to methanol (1.5 L) and stirred vigorously for 10 minutes. The resulting precipitate was filtered and then triturated with a 10:1 mixture of methanol and ethyl acetate (3 x 300 mL) for 2 hours to afford compound 8-II (25 g, 32% yield, >95% HPLC purity) as an off-white solid.

[0428] Compound 8-II (25 g, 70 mmol, 1 equivalent) and 10% palladium on carbon (2.5 g, 50% water wet) were hydrogenated at room temperature for 2.5 hours at 30 psi in a 10:1 mixture (300 mL) of tetrahydrofuran and methanol, at which time LC / MS analysis showed that the reaction was complete. The reaction was filtered through diatomaceous earth (20 g) and washed with tetrahydrofuran (200 mL). The filtrate was concentrated under reduced pressure. The residue was purified through silica gel (800 g) and eluted with a gradient of 5% to 15% ethyl acetate in heptane to obtain compound 8 (12 g, 72% yield, HPLC purity>95%) as a colorless oil that slowly solidified into a white solid within 2 days. 1 H NMR (400MHz, 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=6.3Hz,2H),3.35(s,2H),1.18(d,J=6.4Hz,12H); 13 CNMR(100MHz, CDCl3)δ=145.70,145.56,133.25,130.19,129.42,128.05,125.77,113.01,55.21,44.37,23.15; C 25 H 30 MS (ESI) m / z of N2 [M+H] + The calculated value is 359.2 and the measured value is 359.2.

[0429] Example 7

[0430] Synthesis of 4,4'-methylenebis(N-isopropylaniline) (Compound 19)

[0431]

[0432] Acetic acid (150 mL) was slowly added to a mixture of 4,4'-methylenedianiline (15 g, 75.7 mmol, 1.0 equiv) and acetone (19.6 mL, 265 mmol, 3.5 equiv) at room temperature (slightly exothermic). Zinc (37.5 g, 576.9 mmol, 7.6 equiv) was added in portions at room temperature. After heating at 40°C for 2 hours, the reaction was cooled to room temperature and filtered through a plug of celite and silica gel to remove the zinc. The column was washed with water (4 x 100 mL) and dichloromethane (3 x 100 mL). The filtrate was evaporated under reduced pressure to remove acetic acid. The residue was diluted with a mixture of water (150 mL) and dichloromethane (200 mL). The pH was adjusted to 10 with 20% aqueous sodium hydroxide at 0°C. A white precipitate was formed, which was further diluted with water (500 mL) until completely dissolved. The layers were separated and the aqueous layer was extracted with dichloromethane (2 x 100 mL). The combined organic layers were washed with saturated brine (200 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified on a Biotage automated chromatography system (350 g Biotage, 60 μm silica gel column) eluting with a gradient of 0 to 10% ethyl acetate in hexanes to afford compound 19 (20 g, 93% yield, 97.3% purity) as a light yellow liquid. 1 H NMR (400MHz, CDCl3) δ=7.03–6.99(m,4H),6.57–6.53(m,4H),3.79(s,2H),3.62(spt,J=6.3Hz,2H),3.35(br s,2H),1.22(d,J=6.2Hz,12H); 13 C NMR (101MHz, CDCl3) δ = 145.65 (s, 2C), 130.61 (s, 2C), 129.66 (s, 4C), 113.42 (s, 4C), 44.45 (s, 2C), 40.11, 23.14 (s, 4C); C 19 H 26 MS (ESI) m / z of N2 [M+H] + The calculated value is 283.2 and the measured value is 283.2.

[0433] Example 8

[0434] Synthesis of 4,4'-methylenebis(N-(1-(furan-2-yl)ethyl)aniline) (Compound 20)

[0435]

[0436] 4,4'-methylenedianiline (19.8g, 100mmol, 1 equivalent) was added to a solution of 2-furanylmethyl ketone (27.5g, 250mmol, 2.5 equivalents) and titanium (IV) isopropoxide (28.4g, 100mmol, 1 equivalent) in methanol (200mL), followed by sodium cyanoborohydride (18.9g, 300mmol, 3 equivalents). The mixture was refluxed for three days. After cooling to room temperature, sodium borohydride (about 1.6g) was added in batches until no 2-furanylmethyl ketone 2 remained after TLC analysis. The mixture was diluted with water (200mL) and ethyl acetate (100mL), filtered through diatomaceous earth (150g), and rinsed with ethyl acetate (300mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (3x 200mL). The combined organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified over silica gel (800 g) eluting with a gradient of 10 to 40% ethyl acetate in heptane to give compound 20 (9.17 g, 24% yield) as a light yellow oil, and compound 20-I (10.57 g, 36% yield) as a dark brown oil.

[0437]

[0438] Compound 20-I (29.2 g, 100 mmol, 1 eq) was added to a solution of 2-furanylmethyl ketone 2 (22.0 g, 200 mmol, 2.0 eq) and titanium (IV) isopropoxide (28.4 g, 100 mmol, 1 eq) in methanol (300 mL), followed by sodium cyanoborohydride (18.9 g, 300 mmol, 3 eq). The mixture was refluxed for three days. After cooling to room temperature, sodium borohydride (about 1.6 g) was added in portions until no 2-furanylmethyl ketone residue was detected by TLC analysis. The mixture was diluted with water (200 mL) and ethyl acetate (100 mL), filtered through diatomaceous earth (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 on silica gel (750 g) eluting with 10% ethyl acetate in heptane to give compound 20 (19 g, 49% yield) as a light yellow oil. 1H NMR (400MHz, CDCl3) δ = 7.35 (dd, J = 0.9, 1.8Hz, 1H), 7.31 (dd, J = 0.9, 1.8Hz, 2H), 6.97–6.92 (m, 4H), 6.55–6.47 (m, 4H), 6.32–6.29 (m, 1H) ,6.26(dd,J=1.8,3.2Hz,2H),6.14–6.10(m,2H),4.58(q,J=6.6Hz,2H),3.72(s,2H),1.51(d,J=6.7Hz,6H),1.37(dd,J=6.7,17.4Hz,1H); 13 C NMR(100MHz, CDCl3)δ=157.47,145.13,141.42,131.27,129.56,113.61,110.10,109.99–109.79(m,1 C),105.61,105.04,49.00,48.44,47.60,40.13,21.35,20.96,20.11; MS(ESI)m / z[M+H] of C25H26N2O2 + The calculated value is 387.2 and the measured value is 387.2.

[0439] Example 9

[0440] Synthesis of 4,4'-methylenebis(N-(1-phenylethyl)aniline) (Compound 21)

[0441]

[0442] 4,4'-methylenedianiline (24.75 g, 125 mmol, 1 eq) was added to a solution of acetophenone (37.5 g, 312.5 mmol, 2.5 eq) and titanium (IV) isopropoxide (35.5 g, 125 mmol, 1 eq) in methanol (250 mL), followed by sodium cyanoborohydride (23.6 g, 375 mmol, 3 eq). The mixture was refluxed for 24 hours. After cooling to room temperature, sodium borohydride (about 1.7 g) was added in portions until no acetophenone residue was detected by TLC analysis. The mixture was diluted with water (300 mL) and ethyl acetate (150 mL), filtered through diatomaceous earth (150 g), and rinsed with ethyl acetate (300 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (4 x 200 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified over silica gel (750 g) eluting with a gradient of 10% to 40% ethyl acetate in heptane to give compound 21 (12.6 g, 21% yield) as a white solid and compound 21-I (19.6 g, 43% yield) as a dark brown oil.

[0443]

[0444] Compound 21-I (35.0 g, 112 mmol, 1 equivalent) was added to a solution of acetophenone (26.9 g, 224 mmol, 2.0 equivalents) and titanium isopropoxide (IV) (31.8 g, 112 mmol, 1 equivalent) in methanol (225 mL), followed by sodium cyanoborohydride (17.6 g, 280 mmol, 2.5 equivalents). The mixture was refluxed for three days. After cooling to room temperature, sodium borohydride (about 1.7 g) was added in batches until no acetophenone residue was detected by TLC analysis. The mixture was diluted with water (200 mL) and ethyl acetate (200 mL), filtered through diatomaceous earth (150 g), and rinsed with ethyl acetate (300 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (3 x 200 mL). The combined organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified over silica gel (800 g) eluting with 10% ethyl acetate in heptane to give compound 21 (22.9 g, 50% yield) as a white solid. 1 H NMR (400MHz, CDCl3) δ=7.37–7.27(m,8H),7.24–7.18(m,2H),6.95–6.80(m,4H),4.43(q,J=6.7Hz,2H),3.90(br s,2H),3.66(s,2H),1.49(s,3H),1.48(s,3H); 13 C NMR (100MHz, CDCl3) δ145.53,145.47,130.77,129.47,128.67,126.87,125.93,113.41,60.47,53.74,40.12,25.11,14.29; C 29 H 30 MS (ESI) m / z of N2 [M+H] + The calculated value is 407.2 and the measured value is 407.3.

[0445] Example 10

[0446] Synthesis of Bis(2,2,4-trimethyl-1,2-dihydroquinolin-6-yl)sulfane (Compound 153)

[0447]

[0448] A 250 mL round bottom flask equipped with a stirring bar and a reflux condenser was charged with the substrate 4,4'-thiodiphenylamine (25.17 g; 116.4 mmol) and acetone (34 mL; 463 mmol). The mixture was stirred under a N2 blanket. The substrate was dissolved within a few minutes. The flask was cooled with a cold tap water bath. Zinc (II) trifluoromethanesulfonate (5.67 g; 15.6 mmol) was added in portions to the resulting dark solution 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 about 16 h without external cooling or heating. The reaction mixture was heated (oil bath temperature = 73 ° C) for about 8 hours and then cooled to room temperature overnight. Isopropylidene oxide (27 mL; 0.24 mol) was added to the flask. The reaction mixture was refluxed (oil bath temperature = 85 ° C) for about 8 hours and then cooled to room temperature overnight. Ethyl acetate (50 mL) was added. The resulting mixture was filtered through a celite pad. The filter cake was rinsed with ethyl acetate (10 mL). The volatiles in the combined filtrate were removed under reduced pressure (rotary evaporator; water bath = 55°C). The residue (dark viscous material) was dissolved in toluene (21 mL). The resulting solution was loaded into a 73 mm inner diameter column (silica height = 21 cm) previously prepared with silica gel 60 and 20% ethyl acetate in hexane. The column was eluted with 20% ethyl acetate in hexane. The obtained fractions were analyzed by silica gel TLC (20% ethyl acetate in hexane). The fractions containing the spot at Rf = 0.5 were collected and the volatiles were removed under reduced pressure (rotary evaporator; water bath = 50°C). The obtained light yellow material (about 14 g) was broken into a fine powder. 10% ethyl acetate in a dichloromethane mixture (35 mL) was added and the resulting slurry was stirred (stirring bar) at room temperature for 4 hours. The solid was collected by vacuum filtration, rinsed quickly with several portions of hexanes (total = 100 mL), and dried under vacuum at 40-50 °C for several hours and then at room temperature overnight to give 7.97 g (18% relative to 4,4'-thiodiphenylamine) of compound 153 as a white powder. Representative 1 H and 13 C APT NMR spectra are shown in Figure 4(a) and 4(b) LC-UV analysis showed a purity of 98.2% at 260 nm. The melting point of compound 153 was found to be about 184°C.

[0449] Embodiment 11

[0450] Synthesis of 4,4'-methylenebis(N-isopropyl-2,6-dimethylaniline) (Compound 154)

[0451]

[0452] A 300 mL Parr autoclave was charged with 4,4'-methylenebis(2,6-dimethylaniline) (5.0 g; 19.7 mmol), isopropanol (150 mL), 3% sulfided Pt / C (Johnson Matthey; 40 mg wet weight), and acetone (4.3 mL; 58.6 mmol). The reaction mixture was heated to 130°C. Once at temperature, H2 (set pressure = 300 PSIG) was continuously fed into the autoclave for several hours. The reaction mixture was allowed to stand overnight at room temperature under N2 protection and stirred overnight. At this stage, about 53% monoalkylated intermediate and 27% desired dialkylated product (percent area measured by LC-UV analysis at 260 nm detection) had been formed. The reaction mixture was heated to 180°C. Once at temperature, H2 (set pressure = 500 PSIG) was continuously fed into the autoclave for about 6 hours. After cooling to room temperature, the reaction mixture was filtered through an in-line 0.2 micron glass frit. The autoclave was rinsed with isopropanol (150 mL) and the mixture was filtered through an inline filter. The volatiles in the combined filtrate were removed under reduced pressure (rotary evaporator; water bath = 55°C). The light brown oil obtained was diluted with hexanes (5.5 mL). The solution was loaded onto a 41 mm inner diameter column (silica height = 7.0-7.5") previously prepared with silica gel 60 and 15% ethyl acetate in hexanes. The column was eluted with 15% ethyl acetate in hexanes. The obtained fractions were analyzed by TCL (15% ethyl acetate in hexanes). The fractions containing the spot at Rf = 0.4 were collected, combined and the volatiles were removed under reduced pressure (rotary evaporator; water bath = 50-55°C). The obtained solid was dried under vacuum at 40-50°C for several hours and then dried overnight at room temperature to give 1.81 g (27% relative to 4,4'-methylenebis(2,6-dimethylaniline)) of compound 154 as a light pink solid. Representative 1 H and 13 C APTNMR spectra are Figure 5(a) and 5(b) LC-UV analysis showed a purity of 99.9% at 260 nm. The melting point of compound 154 was found to be about 84-88°C.

[0453] Example 12

[0454] Use of the disclosed compounds in sidewall formulations

[0455] In this study, rubber compounds were prepared using compounds of the present invention as an antidegradant in the sidewall formulation. As shown in Table 2, these rubber compounds are 50 / 50 blends of natural rubber and butadiene rubber with N500 series carbon black. Sidewall compounds containing compounds of the present invention or not containing antidegradants can be seen in the examples listed in Table 2. According to the American Society for Testing and Materials (ASTM) test method D5289, the vulcanization properties of all compounds were characterized by a moving die rheometer (Alpha Technologies MDR 2000) (also referred to as MDR) at a temperature of 160°C for 60 minutes. The vibration strain and frequency were set to 0.5°C and 1.667Hz, respectively. The MDR test results are summarized in Table 3.

[0456] Table 2

[0457]

[0458]

[0459] Table 3

[0460]

[0461]

[0462] 1 ML is the minimum torque, which is a measure of the stiffness and viscosity of an uncured compound.

[0463] 2 MH is the maximum torque which is a measure of the crosslink density of a fully cured compound.

[0464] 3 tMH is the time to reach the maximum torque MH

[0465] 4 Ts1 is the time required for the viscosity to increase by 1 unit (dNm) above ML.

[0466] 5 Ts2 is the time required for the viscosity to increase by 2 units (dNm) above ML.

[0467] 6 T 10 The moment when 10% cross-linking is achieved.

[0468] 7 T 25 The moment when 25% cross-linking is achieved.

[0469] 8 T 50 The moment when 50% cross-linking is achieved.

[0470] 9 T 90 This is the moment when 90% cross-linking is achieved.

[0471] Embodiment 13

[0472] Ozone resistance of the disclosed compounds in sidewall compounds

[0473] Each rubber compound prepared in Example 12 was cured at 150°C or 160°C to a state equivalent to its T90 time. According to the American Society for Testing and Materials (ASTM) D1329 standard, the ozone test sample was demoulded (dieout) from the vulcanized tensile plate using a mold. The ozone test sample was stored in an ozone chamber at ambient temperature for more than 24 hours before the anti-ozone performance test was performed. The ozone chamber maintained an ozone concentration of 10±2 parts per million (pphm) and 40±2°C. The ozone test sample was relaxed and extended simultaneously in the ozone chamber under three different conditions of static, intermittent and dynamic (150°C test) or under dynamic conditions (160°C test). The ozone test sample maintained a strain of 25% during static exposure and alternately relaxed and extended to a strain of 25% at a rate of 90 cycles per minute during dynamic exposure. The intermittent test alternated between 18 minutes of dynamic exposure and 102 minutes of static exposure. Exposure time was measured in 16-hour increments, followed by relaxation for at least one hour after removal from the ozone chamber before measuring the force at 100% strain.

[0474] The ozone resistance of the antidegradant formulated compounds was evaluated by the force retention percentage. The force retention percentage is defined by Equation 1.

[0475] Formula 1:

[0476] Where F0 is the force at 100% strain before ozone testing, and F is the force at 100% strain after the sample is aged in an ozone chamber for 16 hours under static, intermittent or dynamic exposure. A higher force retention percentage indicates better ozone resistance of the anti-degradation compound incorporated into the vulcanized rubber compound.

[0477] The force of aged and unaged ozone test samples was measured at 100% strain using a tensiometer (Alpha Technologies, 2000). The force retention percentage was calculated and reported in Figure 6(a)-6(c) (150℃ test) and Figure 7 (160°C test) is plotted as a function of ozone aging time.

[0478] Embodiment 14

[0479] Oxidation Induction Time (OIT) Performance of the Disclosed Compounds

[0480] In order to demonstrate the antioxidant efficacy of the compounds disclosed herein, the oxidation induction time (OIT) of the selected examples was evaluated. OIT is measured according to the procedure performed in a differential scanning calorimeter (TA Instruments, Q200) (also referred to as DSC), and is used to predict the thermal oxidation performance of the material. In this procedure, each sample is kept in a sample cell and heated to a preselected temperature under a nitrogen atmosphere. Oxygen is then introduced into the sample cell and the length of time before degradation begins (as observed by the start of heat flow increase) is measured.

[0481] 0.5 wt% of the compound of the present disclosure, N 1 -(4-methylpentan-2-yl)-N 4 -phenylbenzene-1,4-diamine (6PPD) or no antidegradant (blank) was mixed with polyisoprene and heated isothermally at 150°C and / or 160°C in O2. Table 4 shows the peak time (minutes) of the OIT test. As shown in the data in Table 4, the molecules of the present invention exhibit certain antioxidant properties compared to the blank control, indicating that they have practical application in rubber and other applications that can benefit from active antioxidants.

[0482] Table 4

[0483]

[0484] Embodiment 15

[0485] Use of the disclosed compounds in tread compounds

[0486] Rubber compounds were prepared using the compounds of the present disclosure as antidegradants in tread formulations. As shown in Table 5, these rubber compounds were 70 / 30 mixtures of styrene-butadiene rubber and butadiene rubber with silica and carbon black. The vulcanization properties of all compounds were characterized by a moving die rheometer (Alpha Technologies MDR 2000) (also known as MDR) at a temperature of 160°C for 60 minutes according to the American Society for Testing and Materials (ASTM) test method D5289. The vibration strain and frequency were set to 0.5°C and 1.667Hz, respectively. The MDR test results are summarized in Table 6.

[0487] Table 5

[0488]

[0489] Table 6

[0490] Materials (Example #1) 1 3 7 8 16 19 20 21 Temperature(℃) 160 160 160 160 160 160 160 160 <![CDATA[ML(dNm) 1 ]]> 3.1 3.1 2.6 2.5 2.5 2.5 2.5 2.5 <![CDATA[MH(dNm) 2 ]]> 38.1 29.7 29.5 29.0 29.5 29.3 29.5 29.2 <![CDATA[tMH(min) 3 ]]> 59.9 59.7 59.7 59.4 59.7 59.8 60.0 59.5 <![CDATA[Ts1(min) 4 ]]> 0.8 0.4 0.5 0.5 0.5 0.5 0.5 0.5 <![CDATA[Ts2(min) 5 ]]> 1.1 0.8 1.0 1.1 1.1 1.1 1.1 1.2 <![CDATA[T 10 (min) 6 ]]> 1.6 1.2 1.5 1.6 1.7 1.7 1.6 1.7 <![CDATA[T 25 (min) 7 ]]> 2.4 2.6 3.5 3.9 4.0 4.1 4.0 4.3 <![CDATA[T 50 (min) 8 ]]> 3.8 3.9 5.0 5.5 5.6 5.8 5.6 6.0 <![CDATA[T 90 (min) 9 ]]> 30.1 23.8 17.4 18.5 18.4 18.5 18.6 19.4

[0491] 1 ML is the minimum torque, which is a measure of the stiffness and viscosity of an uncured compound.

[0492] 2 MH is the maximum torque which is a measure of the crosslink density of a fully cured compound.

[0493] 3 tMH is the time to reach the maximum torque MH

[0494] 4 Ts1 is the time at which the viscosity increases by 1 unit (dNm) above ML.

[0495] 5 Ts2 is the time at which the viscosity increases 2 units (dNm) above ML.

[0496] 6 T 10 The moment when 10% cross-linking is achieved.

[0497] 7 T 25 The moment when 25% cross-linking is achieved.

[0498] 8 T 50 The moment when 50% cross-linking is achieved.

[0499] 9 T 90 This is the moment when 90% cross-linking is achieved.

[0500] Example 16

[0501] Use of the disclosed compounds in tread compounds

[0502] Each rubber compound prepared in Example 15 was cured at 160°C to a state equivalent to its T90+2min time. According to the American Society for Testing and Materials (ASTM) D1329 standard, the ozone test sample was demoulded from the vulcanized tensile plate using a mold. The ozone test sample was stored in an ozone chamber at ambient temperature for more than 24 hours before the ozone resistance performance test was performed. The ozone chamber maintained an ozone concentration of 10±2 parts per million (pphm) and 40±2°C. The ozone test sample was relaxed and extended simultaneously in the ozone chamber under dynamic conditions. The ozone test sample was extended to a strain of 25% at a rate of 90 cycles per minute during dynamic exposure. The exposure time was in increments of 16 hours, and then relaxed for at least one hour after being removed from the ozone chamber, and then the force at 100% strain was measured.

[0503] The ozone resistance of the antidegradant formulated compounds was evaluated by the force retention percentage. The force retention percentage is defined by Equation 1 above.

[0504] The force of aged and unaged ozone test samples was measured at 100% strain using a tensiometer (Alpha Technologies, 2000). The force retention percentage was calculated and reported in Figure 8 The plot is as a function of ozone aging time.

[0505] Now that the methods, compounds and compositions herein have been fully described, it will be understood by those skilled in the art that the same operations can be performed within a broad and equivalent range of conditions, formulations and other parameters without affecting the scope of the methods, compounds and compositions provided herein or any embodiment thereof. All patents, patent applications and publications cited herein are fully incorporated herein by reference in their entirety.

Claims

1. A compound having formula (I): or a salt or solvate thereof, wherein: R 1 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 the nitrogen atom and the carbon atom to which they are attached, they form a saturated or partially saturated optionally substituted 5- or 6-membered heterocyclic ring; R 1a Selected from the group consisting of optionally substituted phenyl, C3-C6 cycloalkyl and optionally substituted 5 or 6 membered heteroaryl; R 1b Selected from the group consisting of hydrogen and C1-C6 alkyl; R 2 Selected from the group consisting of: C1-C 12 Alkyl, -CHR 2a R 2b , C3-C6 cycloalkyl, and optionally substituted phenyl; or R 2 and R 8 Together with the nitrogen atom and the carbon atom to which they are attached, they form a saturated or partially saturated optionally substituted 5- or 6-membered heterocyclic ring; R 2a Selected from the group consisting of optionally substituted phenyl, C3-C6 cycloalkyl and optionally substituted 5 or 6 membered heteroaryl; R 2b Selected from the group consisting of hydrogen and C1-C6 alkyl; X-Select Free-CHR 3a -、-NR 3b -, -O-, and -S-; R 3a Selected from the group consisting of: 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 Selected from the group consisting of: 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 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 atom and the carbon atom to which they are attached, they form a saturated or partially saturated optionally substituted 5- or 6-membered heterocyclic ring; and 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; and R 8 , R 9 , R 10 and R 11 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 the nitrogen atom and the carbon atom to which they are attached, they form a saturated or partially saturated optionally substituted 5- or 6-membered heterocyclic ring; and R 9 , R 10 and R 11 Independently selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy and C1-C6 alkylthio.

2. The compound of 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 of claim 1, or a salt or solvate thereof, wherein X is -CHR 3a -.

6. The compound of claim 5, which has formula (II): or a salt or solvate thereof, wherein R 3a Selected from the group consisting of: C1-C 12 alkyl, C3-C6 cycloalkyl, optionally substituted phenyl and optionally substituted 5- or 6-membered heteroaryl, The condition is Not equivalent to 7. The compound of claim 5, which has formula (III): or a salt or solvate thereof, wherein R 3a Selected from the group consisting of: C1-C 12 alkyl, C3-C6 cycloalkyl, optionally substituted phenyl and optionally substituted 5- or 6-membered heteroaryl, The condition is Not equivalent to 8. The compound according to any one of claims 1 to 7, or a salt or solvate thereof, wherein R 1 and R 2 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.

9. The compound according to claim 8, or a salt or solvate thereof, wherein R 1 and R 2 It is isopropyl.

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

11. The compound according to claim 10, or a salt or solvate thereof, wherein R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 It's hydrogen.

12. The compound according to any one of claims 1 or 5 to 11, or a salt or solvate thereof, wherein: R 3a Selected from the group consisting of: C1-C12 alkyl, and Q is -NH-, -O- or -S-.

13. The compound according to claim 12, or a salt or solvate thereof, wherein R 3a It is a C1-C12 alkyl group.

14. The compound according to claim 13, or a salt or solvate thereof, wherein R 3a It is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl.

15. The compound according to claim 12, or a salt or solvate thereof, wherein R 3a yes 16. The compound of claim 15, or a salt or solvate thereof, wherein Q is -O-.

17. The compound of claim 5, or a salt or solvate thereof, having formula (IV): or a salt or solvate thereof, wherein: Each is a single bond or a double bond; and R 1c , R 1d , R 1e , R 2c , R 2d and R 2e Independently selected from the group consisting of hydrogen and C1-C6 alkyl.

18. The compound of claim 5, or a salt or solvate thereof, having formula (IVa): or a salt or solvate thereof, wherein: Each is a single bond or a double bond; R 1c , R 1d , R 1e , R 2c , R 2d and R 2e independently selected from the group consisting of hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl; R 1f and R 2f 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' at each occurrence are independently selected from the group consisting of hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl; and R 1g , R 2g , R 1i and R 2i independently selected from the group consisting of hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl and optionally substituted phenyl, The condition is that if the connection with R 1e and R 1i Connected Carbon is a double bond, then R 1e and R 1i does not exist, and if connected with R 2e and R 2i Connected Carbon is a double bond, then R 2e and R 2i Does not exist.

19. The compound of claim 17, or a salt or solvate thereof, having formula (V): or a salt or solvate thereof, The condition is Not equivalent to 20. The compound of claim 18, or a salt or solvate thereof, having formula (Va): or a salt or solvate thereof, The condition is Not equivalent to 21. The compound of claim 17, or a salt or solvate thereof, having formula (VI): or a salt or solvate thereof, The condition is Not equivalent to 22. The compound of claim 18, or a salt or solvate thereof, having formula (VIa): or a salt or solvate thereof, The condition is Not equivalent to 23. The compound according to any one of claims 17 to 22, or a salt or solvate thereof, wherein R 5 , R 6 , R 7 , R 9 , R 10 and R 11 Selected from the group consisting of hydrogen, methyl, C1-C6 alkoxy and C1-C6 alkylthio.

24. The compound of claim 23, or a salt or solvate thereof, wherein R 5 , R 6 , R 7 , R 9 , R 10 and R 11 It's hydrogen.

25. A compound as described in any one of claims 17 to 24, or a salt or solvate thereof, wherein R 1c , R 1d , R 1e , R 2c , R 2d and R 2e is methyl, ethyl or hydrogen.

26. The compound of claim 25, or a salt or solvate thereof, wherein R 1c , R 1d , R 1e , R 2c , R 2d and R 2e It's methyl.

27. A compound as described in any one of claims 17, 18 or 23-26, or a salt or solvate thereof, wherein R 3a It's hydrogen.

28. A compound as claimed in any one of claims 17 to 26, or a salt or solvate thereof, wherein: R 3a Selected from the group consisting of: C1-C 12 alkyl and Q is -NH-, -O- or -S-.

29. The compound of claim 28, or a salt or solvate thereof, wherein R 3a It is C1-C 12 alkyl.

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

31. The compound of claim 28, or a salt or solvate thereof, wherein R 3a yes:

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

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

34. A composition comprising: (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 antidegradant; 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 antidegradant.

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

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

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

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

39. The composition of claim 37 or 38, wherein the natural rubber comprises rubber derived from an alternative rubber plant.

40. The composition of claim 39, wherein the alternative rubber plant is Guayule (Guayule) or Rubber Grass (Russian Taraxacum).

41. The composition of any one of claims 35-40, wherein the one or more elastomers comprises a synthetic rubber.

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

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

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

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

46. ​​The composition of any one of claims 43-45, wherein the unsaturated rubber comprises polybutadiene rubber (BR).

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

48. The composition of any one of claims 43-47, wherein the unsaturated rubber comprises butyl rubber (IIR).

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

50. The composition of any one of claims 42-49, wherein the saturated rubber comprises acrylic rubber (ACM), chlorinated polyethylene (CM), chlorosulfonated polyethylene (CSM), polychloromethylethylene oxide (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 of any one of claims 34-50, wherein the one or more elastomers further comprises reclaimed rubber.

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

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

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

55. The composition of any one of claims 34-54, wherein the composition comprises one or more fillers.

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

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

59. The composition of claim 58, wherein the one or more fillers comprises silicon dioxide.

60. The composition of claim 59, wherein the silica is derived from rice husks.

61. The composition of any one of claims 54-60, wherein the one or more fillers comprises carbon black.

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

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

66. The composition of any one of claims 62-65, wherein the one or more rubber chemicals include one or more vulcanizing agents, one or more accelerators, one or more activators, one or more pre-vulcanization inhibitors, or a combination thereof.

67. The composition of claim 66, wherein the one or more rubber chemicals include one or more vulcanizing agents.

68. The composition of claim 67, wherein the one or more vulcanizing agents comprises sulfur, a peroxide, a resin, or a combination thereof.

69. The composition of claim 68, wherein the sulfur is octasulfur (S8), cyclododecyl sulfide (S12), polymeric sulfur, or a combination thereof.

70. The composition of claim 68, wherein the peroxide is 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 a combination thereof.

71. The composition of claim 68, wherein the resin is a bonding resin.

72. The composition of claims 66-71, wherein the one or more rubber chemicals include one or more accelerators.

73. The composition of claim 72, wherein the one or more accelerators comprise guanidine, thiazole, sulfenamide, thiuram, dithiocarbamate, xanthate, thiophosphate, or a combination thereof.

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

75. The composition of claim 73, wherein the thiazole comprises 2-mercaptobenzothiazole (MBT), zinc 2-mercaptobenzothiazole (ZMBT), mercaptobenzothiazole disulfide (MBTS), N-tert-butyl-2-benzothiazolesulfenyl imide (TBSI), or a combination thereof.

76. The composition of claim 73, wherein the sulfenamide comprises N-tert-butyl-2-benzothiazolesulfenamide (TBBS), N-cyclohexylbenzothiazole-2-sulfenamide (CBS), dicyclohexyl-2-benzothiazolesulfenamide (DCBS), N-oxydivinylbenzothiazolesulfenamide (OBTS), N-oxydivinylthiocarbamoyl-N'-oxydivinylsulfenamide (OTOS), thiocarbamoylsulfenamide, or a combination thereof.

77. The composition of claim 73, wherein the thiuram is dimethylthiocarbamic acid dithioperoxyanhydride (thiram), dipentamethylenethiuram tetrasulfide (DPIT), tetrabenzylthiuram disulfide (TBzTD), tetraethylthiuram disulfide (TETD), tetramethylthiuram disulfide (TMTD), tetramethylthiuram monosulfide (TMTM), or a combination thereof.

78. The composition of claim 73, wherein the dithiocarbamate comprises zinc dimethyldithiocarbamate (ZDMC), zinc diethyldithiocarbamate (ZDEC), 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 of any one of claims 66-78, wherein the one or more rubber chemicals include one or more activators.

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

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

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

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

84. The composition of any one of claims 66-83, wherein the one or more rubber chemicals include one or more pre-vulcanization inhibitors.

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

86. A composition as described in any one of claims 34-85, wherein the composition comprises one or more plasticizers.

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

90. The composition of any one of claims 86-89, wherein the one or more plasticizers comprise mineral oils, organic esters, resins, waxes, ester plasticizers, oils of natural origin, or combinations thereof.

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

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

93. The composition of any one of claims 34-92, wherein the composition further comprises a second antidegradant.

94. The composition of claim 93, wherein the composition comprises from about 15% to about 85% w / w of the compound and from about 15% to about 85% w / w of a second antidegradant.

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

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

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

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

99. The composition of any one of claims 93-98, wherein the second antidegradant is an antioxidant.

100. The composition of any one of claims 93-98, wherein the second antidegradant is an antiozonant.

101. The composition of any one of claims 93-100, wherein the second antidegradant is p-phenylenediamine (PPD), trimethyldihydroquinoline (TMQ), phenols, alkylated diphenylamine (DPA) or diphenylamine-ketone condensate.

102. The composition of claim 101, wherein the PPD is N 1 -(4-methylpentan-2-yl)-N 4 -phenylbenzene-1,4-diamine (6PPD), N-(1,4-dimethylpentyl)-N'-phenyl-p-phenylenediamine (7PPD), N 1 -phenyl-N 4 -(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).

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

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

105. A composition comprising a compound of any one of claims 1-33 and one or more carriers.

106. A method for preparing the composition of claim 105, comprising mixing the compound with the one or more carriers.

107. A vulcanized elastomeric article comprising the compound of any one of claims 1-33.

108. A vulcanized elastomeric article prepared using the composition of any one of claims 34-105.

109. The vulcanized elastomeric article of claim 107 or 108, wherein the vulcanized elastomeric article is a tire.

110. The vulcanized elastomeric article of 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 bulldozer tire, an aircraft tire, or a racing tire.

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

112. The vulcanized elastomeric article of claim 111, wherein the component is a bead, a belt, a carcass ply, an innerliner, a sidewall, an undertread, or a tread.

113. The vulcanized elastomeric article of claim 107 or 108, wherein the vulcanized elastomeric article is a rubber overshoe, a weatherstrip, a soundproofing panel, an air spring, a bellows, a membrane, a tactile sensor, an anti-vibration pad, a hose, a conveyor belt, or a floor.

114. A method for preparing a vulcanized elastomeric article, the method comprising: (a) forming the composition of any one of claims 33 to 105 into a shaped shape; and (b) Vulcanizing the formed shape To provide a vulcanized elastomeric product.

115. The method of claim 114, wherein the vulcanization is performed at an average temperature of about 120°C to about 180°C.

116. The method of claim 115, wherein the vulcanization is performed at an average temperature of about 140°C to about 160°C.

117. The method of any one of claims 114-116, wherein the vulcanized elastomeric article is a tire.

118. The method of 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 bulldozer tire, an aircraft tire, or a racing tire.

119. The method of any one of claims 114-118, wherein the vulcanized elastomeric article is a component of a tire.

120. The method of claim 119, wherein the component is a bead, a belt, a carcass ply, an innerliner, a sidewall, an undertread, or a tread.

121. The method of any one of claims 114-116, wherein the vulcanized elastomeric article is a rubber overshoe, a weatherstrip, a soundproofing panel, an air spring, a bellows, a membrane, a tactile sensor, an anti-vibration pad, a hose, a conveyor belt, or a floor.

122. A lubricant composition comprising a lubricant and the compound of any one of claims 1-33.

123. A combustible fuel composition comprising a combustible fuel and a compound as described in any one of claims 1-33.

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

125. A method for retreading a tire, the method comprising: (a) applying the composition of any one of claims 34 to 105 to a tire; (b) providing a pre-cured tread around the tire; (c) providing a curing envelope around the tire; and (d) vulcanizing the tire.

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

127. A kit comprising the composition of any one of claims 34-105 and instructions for using the composition to prepare a vulcanized elastomeric article.

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

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