Aminoindole anti-degradation compounds and uses thereof

Abstract

The present disclosure provides a composition comprising a compound represented by formula (I): # imgabs0 # or a salt or solvate thereof wherein R1, R2a, R2b, R2c, R3a, R3b and (II) are as defined in the specification. The present disclosure also provides vulcanized elastomeric articles, lubricant compositions, combustible fuel compositions, and fuel additive compositions comprising the compounds or compositions described herein. The present disclosure also provides methods for making the compositions and vulcanized elastomeric articles described herein. The present disclosure also provides methods of retreading a tire using the compounds or compositions described herein. The present disclosure also provides kits comprising the compounds or compositions described herein.

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. Background Art

[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 obviously must 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. As 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 mechanical fatigue life after product 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, 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 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, uninflated, and flexed throughout its service life. U.S. Pat. No. 8,833,417 describes an antioxidant system that is said to provide greater long-term fatigue and crack growth resistance than 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 such are generally favored by many tire manufacturers for this purpose. EP 3147321A1 discloses rubber compositions, tires, amine compounds and anti-aging agents, in particular rubber compositions said to be suitable for tread rubber or sidewall rubber of tires. U.S. Patent No. 3,362,930 discloses 6-anilino-2,2,4-trimethyl-1,2-dihydroquinoline and its use as an antiozonant in a rubber composition. 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)-(VII), 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] Figure 1 To depict the 6 -dimethyl sulfoxide (d 6 -DMSO) 1 Line graph of the H nuclear magnetic resonance (NMR) spectrum.

[0042] Figure 2 To depict the 6 -dimethyl sulfoxide (d 6 -DMSO) 13 Line graph of C NMR spectrum.

[0043] 3(a)-(c) are line graphs showing the force retention of sidewall compounds comprising Compound 1 as a function of time under (a) static, (b) intermittent, and (c) dynamic conditions.

[0044] Figure 4 To depict the 6 -dimethyl sulfoxide (d 6-DMSO) of compound 2 1 Line graph of the H NMR spectrum.

[0045] Figure 5 To depict the 6 -dimethyl sulfoxide (d 6 -DMSO) 13 Line graph of C NMR spectrum.

[0046] Figure 6 To depict the 6 -dimethyl sulfoxide (d 6 -DMSO) in compound 19 1 Line graph of the H NMR spectrum.

[0047] Figure 7 To depict the 6 -dimethyl sulfoxide (d 6 -DMSO) in compound 19 13 Line graph of CNMR spectrum. DETAILED DESCRIPTION

[0048] In one embodiment, the compound of the present disclosure is a compound having formula (I):

[0049]

[0050] or a salt or solvate thereof, wherein:

[0051] is a single bond or a double bond;

[0052] R 1 Selected from the group consisting of: C 1 -C 12 Alkyl, -CHR 1a R 1b , optionally substituted C 3 -C 6 cycloalkyl, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;

[0053] R 1a is selected from the group consisting of: optionally substituted phenyl, optionally substituted C 3 -C 6 cycloalkyl, optionally substituted 4- to 6-membered heterocyclyl, and optionally substituted 5- or 6-membered heteroaryl;

[0054] R 1b Selected from hydrogen and C 1 -C 9 A group consisting of alkyl groups;

[0055] R2a , R 2b and R 2c independently selected from the group consisting of hydrogen, halogen, C 1 -C 9 Alkyl, C 1 -C 9 haloalkyl, optionally substituted C 3 -C 8 Cycloalkyl, -OH, C 1 -C 8 Alkoxy, -SH, C 1 -C 8 Alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5 or 6 membered heteroaryl; or

[0056] R 2a and R 2b Together with the two carbon atoms to which they are attached, they form an optionally substituted C 3 -C 6 cycloalkyl, optionally substituted 4 to 6 membered heterocyclyl, optionally substituted 4 to 6 membered aryl, or optionally substituted 4 to 6 membered heteroaryl; and

[0057] R 2c Selected from the group consisting of: hydrogen, halogen, C 1 -C 9 Alkyl, C 1 -C 9 haloalkyl, optionally substituted C 3 -C 8 Cycloalkyl, -OH, C 1 -C 8 Alkoxy, -SH, C 1 -C 8 Alkylthio, -C(=O)OR 4 、-OC(=O)R 4、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5 or 6 membered heteroaryl;

[0058] R 3a and R 3b independently selected from the group consisting of hydrogen, halogen, C 1 -C 9 Alkyl, C 1 -C 9 haloalkyl, optionally substituted C 3 -C 8 Cycloalkyl, -OH, C 1 -C 8 Alkoxy, -SH, C 1 -C 8 Alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5 or 6 membered heteroaryl; or

[0059] R 3a and R 3b Together with the two carbon atoms to which they are attached, they form an optionally substituted C 3 -C 12cycloalkyl or an optionally substituted 4- to 6-membered heterocyclic group;

[0060] R 4 Selected from hydrogen and C 1 -C 9 alkyl; and

[0061] R 5 Selected from hydrogen and C 1 -C 9 Alkyl group.

[0062] In some embodiments, the compounds of the present disclosure are compounds having formula (I), wherein It's a double bond.

[0063] In some embodiments, the compounds of the present disclosure are compounds having formula (I), wherein It is a single bond.

[0064] In some embodiments, the compounds of the present disclosure are compounds having formula (I), wherein R 3a and R 3b Selected from hydrogen and C 1 -C 6 Alkyl group.

[0065] In some embodiments, the compounds of the present disclosure are compounds having formula (I), wherein R 3a and R 3b It's hydrogen.

[0066] In one embodiment, the compound of the present disclosure is a compound having formula (II):

[0067]

[0068] or a salt or solvate thereof, wherein:

[0069] R 1 , R 2a , R 2b , R 2c , R 3a and R 3b Definitions of formula (I):

[0070] The condition is R 3a and R 3b At least one of them is not hydrogen.

[0071] In some embodiments, the compounds of the present disclosure are compounds having formula (III):

[0072]

[0073] or a salt or solvate thereof, wherein:

[0074] R 1 , R 2a , R 2b , R 2c , R 3a and R 3b Definitions of formula (I):

[0075] The condition is R 3a and R 3b At least one of them is not hydrogen.

[0076] In another embodiment, the compound of the present disclosure is a compound having formula (IV):

[0077]

[0078] or a salt or solvate thereof, wherein:

[0079] R 1 , R 2a , R 2b , R 2c , R 3a and R 3b Definitions of formula (I):

[0080] The condition is R 3a and R 3b Not hydrogen.

[0081] In some embodiments, the compounds of the present disclosure are compounds having Formula (V):

[0082]

[0083] or a salt or solvate thereof, wherein:

[0084] R 1 , R 2a , R 2b , R 2c , R 3a and R 3b Definitions of formula (I):

[0085] The condition is R 3a and R 3b Not hydrogen.

[0086] In some embodiments, the compounds of the present disclosure are compounds having Formula (VI):

[0087]

[0088] or a salt or solvate thereof, wherein:

[0089] X 1Selected from the group consisting of: -CR 6c R 6d -, -O-, -S-, and -NH-;

[0090] X 2 Selected from the group consisting of: -(CR 6e R 6f ) p -, -O-, -S-, and -NH-;

[0091] p is 1 or 2;

[0092] R 6a and R 6b independently selected from hydrogen and C 1 -C 6 alkyl; or

[0093] R 6a and R 6b Together with the carbon atom to which they are attached they form an oxo group, i.e. -C(=O)-;

[0094] R 6c and R 6d independently selected from hydrogen and C 1 -C 6 A group consisting of alkyl groups;

[0095] Each R 6e and R 6f independently selected from hydrogen and C 1 -C 6 alkyl; and

[0096] R 1 , R 2c , R 3a , R 3b and Definition of formula (I).

[0097] In some embodiments, the compounds of the present disclosure are compounds having Formula (VII):

[0098]

[0099] or a salt or solvate thereof, wherein:

[0100] Z is selected from the group consisting of: -CR 7a =CR 7b -CR 7c =CR 7d -、-CR 7a =CR 7b -CHR 7c -CHR 7d -、-CHR7a -CHR 7b -CHR 7c -CHR 7d -、-CR 7a =CR 7b -CHR 7c -and-CHR 7a -CHR 7b -CHR 7c -;

[0101] R 7a , R 7b , R 7c and R 7d independently selected from the group consisting of hydrogen, halogen, C 1 -C 9 Alkyl, C 1 -C 9 haloalkyl, optionally substituted C 3 -C 8 Cycloalkyl, -OH, C 1 -C 8 Alkoxy, -SH, C 1 -C 8 Alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5 or 6 membered heteroaryl; and

[0102] R 1 , R 2c , R 3a , R 3b , R 4 , R 5 and Definition of formula (I).

[0103] In some embodiments, the compounds of the present disclosure are compounds having formula (VII), wherein Z is -CR 7a=CR 7b -CR 7c =CR 7d -. In some embodiments, R 7a , R 7b , R 7c and R 7d For hydrogen.

[0104] In some embodiments, the compounds of the present disclosure are compounds having formula (VII), wherein Z is -CR 7a =CR 7b -CHR 7c -CHR 7d -. In some embodiments, R 7a , R 7b , R 7c and R 7d For hydrogen.

[0105] In some embodiments, the compounds of the present disclosure are compounds having formula (VII), wherein Z is -CHR 7a -CHR 7b -CHR 7c -CHR 7d -. In some embodiments, R 7a , R 7b , R 7c and R 7d For hydrogen.

[0106] In some embodiments, the compounds of the present disclosure are compounds having formula (VII), wherein Z is -CR 7a =CR 7b -CHR 7c -. In some embodiments, R 7a , R 7b and R 7c For hydrogen.

[0107] In some embodiments, the compounds of the present disclosure are compounds having formula (VII), wherein Z is -CHR 7a -CHR 7b -CHR 7c -. In some embodiments, R 7a , R 7b and R 7c For hydrogen.

[0108] In some embodiments, the compounds of the present disclosure are compounds having formula (VII), wherein It's a double bond.

[0109] In some embodiments, the compounds of the present disclosure are compounds having formula (VII), wherein It is a single bond.

[0110] In some embodiments, the compounds of the present disclosure are of formula (I), wherein R 1 Selected from the group consisting of: -CHR 1a R 1b , optionally substituted 4- to 6-membered heterocyclyl, and optionally substituted 5- or 6-membered heteroaryl.

[0111] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(VII), wherein R 1 Choose from C 1 -C 12 The group consisting of an alkyl group and an optionally substituted phenyl group.

[0112] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(VII), wherein R 1 It is phenyl.

[0113] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(VII), wherein R 1 Selected from the group consisting of methyl, ethyl, propyl, isopropyl, tert-butyl, sec-butyl, isobutyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl.

[0114] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(VII), wherein R 1 It is sec-butyl.

[0115] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(VII), wherein R 1 It is isopropyl.

[0116] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(VII), wherein R 1 Yes - CHR 1a R 1b .

[0117] In some embodiments, the compounds of the present disclosure are of formula (I), wherein R 1a is selected from the group consisting of optionally substituted 4 to 6 membered heterocyclyl and optionally substituted 5 or 6 membered heteroaryl.

[0118] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(VII), wherein R 1a Selected from the group consisting of:

[0119] and

[0120] Q is selected from the group consisting of -NH-, -O- and -S-.

[0121] In some embodiments, the compound of the present disclosure is a compound of any one of Formula (I)-(VII), wherein Q is -O-.

[0122] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(VII), wherein R 1a Selected from the group consisting of:

[0123]

[0124] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(VII), wherein R 1b is selected from the group consisting of hydrogen and methyl.

[0125] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(V), wherein R 2a , R 2b and R 2c independently selected from the group consisting of hydrogen, halogen, C 1 -C 9 Alkyl, C 1 -C 6 Alkoxy and C 1 -C 6 Alkylthio.

[0126] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(V), wherein R 2a Selected from the group consisting of: C 1 -C 9 Alkyl, C 1 -C 6 Alkoxy and C 1 -C 6 alkylthio; and R 2b and R 2c It's hydrogen.

[0127] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(V), wherein R 2b Selected from the group consisting of: C 1 -C 9 Alkyl, C 1 -C 6 Alkoxy and C 1 -C 6 alkylthio; and R 2a and R2c It's hydrogen.

[0128] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(V), wherein R 2c Selected from the group consisting of: C 1 -C 9 Alkyl, C 1 -C 6 Alkoxy and C 1 -C 6 alkylthio; and R 2a and R 2b It's hydrogen.

[0129] In some embodiments, the compounds of the present disclosure are compounds of any one of Formula (I)-(V), wherein R 2a , R 2b and R 2c It's hydrogen.

[0130] In some embodiments, the compounds of the present disclosure are compounds of formula (I), wherein:

[0131] R 3a Selected from the group consisting of: hydrogen, halogen, C 1 -C 9 Alkyl, C 1 -C 9 haloalkyl, optionally substituted C 3 -C 8 Cycloalkyl, -OH, C 1 -C 8 Alkoxy, -SH, C 1 -C 8 Alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5 or 6 membered heteroaryl; and

[0132] R3b Selected from the group consisting of: hydrogen, halogen, C 1 -C 9 Alkyl, C 1 -C 9 Haloalkyl, -OH, C 1 -C 8 Alkoxy, -SH, C 1 -C 8 Alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, and optionally substituted 5 or 6 membered heteroaryl; or

[0133] R 3a and R 3b Together with the two carbon atoms to which they are attached, they form an optionally substituted C 3 -C 12 Cycloalkyl or an optionally substituted 4- to 6-membered heterocyclic group.

[0134] In some embodiments, the compounds of the present disclosure are compounds of formula (I), provided that when R 1 yes:

[0135]

[0136] R 2a , R 2b and R 2c is hydrogen, R 3a is hydrogen, and When it is a double bond, R 3b Selected from the group consisting of: hydrogen, halogen, C 1 -C 9 Alkyl, C 1 -C 9 Haloalkyl, -OH, C 1 -C 8 Alkoxy, -SH, C 1 -C8 Alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4- to 6-membered heterocyclyl, and optionally substituted 5- or 6-membered heteroaryl.

[0137] In some embodiments, the compound of the present disclosure is a compound of formula (I), with the proviso that the compound is not:

[0138]

[0139] 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.

[0140] Table 1

[0141]

[0142]

[0143]

[0144]

[0145]

[0146] 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.

[0147] The compounds of the present disclosure can be prepared by reacting 5-aminoindole or 5-aminoindoline with an aldehyde or ketone via reductive alkylation, as shown in Scheme 1.

[0148] Solution 1

[0149]

[0150] definition

[0151] 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., C 1 -C 12 Alkyl, or specify the number of carbon atoms, for example, C 1 -C 3 Alkyl, such as methyl, ethyl, propyl or isopropyl; C 1 -C 4 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 C 1 -C 8 In another embodiment, the alkyl group is C 1 -C 6 In another embodiment, the alkyl group is C 1 -C 4 In another embodiment, the alkyl group is C 1 -C 3 Non-limiting exemplary C 1 -C 12 Alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, 3-pentyl, hexyl, heptyl, octyl, nonyl and decyl.

[0152] As used herein, the term "halo" or "halogen" by itself or as part of another group refers to -Cl, -F, -Br or -I.

[0153] As used herein, the term "nitro" by itself or as part of another group refers to -NO 2 .

[0154] As used herein, the term "cyano" by itself or as part of another group refers to -CN.

[0155] As used herein, the term "hydroxy" by itself or as part of another group refers to -OH.

[0156] As used herein, the term "amino" by itself or as part of another group refers to a radical of the formula -NR 1f R 1g A group in which R 1f and R 1g are independently hydrogen or alkyl.

[0157] In one embodiment, the amino group is -NH 2 .

[0158] In another embodiment, the amino group is an "alkylamino" group, ie, wherein R 1f It is C 1-6 Alkyl and R 1g In one embodiment, R 1f It is C 1 -C 4 Non-limiting exemplary alkylamino groups include -N(H)CH 3 and -N(H)CH 2 CH 3 .

[0159] In another embodiment, the amino group is a "dialkylamino" group, i.e., wherein R 1f and R 1g Each is independently C 1-6 In one embodiment, R 1f and R 1g Each is independently C 1 -C 4 Non-limiting exemplary dialkylamino groups include -N(CH 3 ) 2 and -N(CH 3 )CH 2 CH(CH 3 ) 2 .

[0160] 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. 1 -C 4 Alkyl. A non-limiting exemplary alkylcarbonyl group is -COCH 3 .

[0161] As used herein, the term "haloalkyl" by 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 C 1 -C 6 Alkyl and the resulting haloalkyl is called "C 1 -C 6 In another embodiment, the alkyl group is C 1 -C 4 Alkyl and the resulting haloalkyl is called "C 1 -C 4 In another embodiment, the alkyl group is C1 or C 2 Alkyl. Non-limiting exemplary haloalkyl groups include fluoromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, 4,4,4-trifluorobutyl, and trichloromethyl groups.

[0162] 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 C 1 -C 6 alkyl, and the resulting alkoxy group is called a "C 1 -C 6 In another embodiment, the alkyl group is C 1 -C 4 The alkyl group, and thus the resulting alkoxy group, is referred to as a "C 1 -C 4 Non-limiting exemplary alkoxy groups include methoxy, ethoxy, and tert-butoxy.

[0163] 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. 1 -C 6 alkyl, and the resulting alkylthio group is referred to as "C 1 -C 6 In one embodiment, the alkyl group is C 1 -C 4 The alkyl group and the resulting alkylthio group are referred to as "C 1 -C 4 Non-limiting exemplary alkylthio groups include -SCH 3 and-SCH 2 CH 3 .

[0164] 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., C 3 -C 12 cycloalkyl), or specify the number of carbon atoms (e.g. C 3 -C 6 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 C 3 -C8 In another embodiment, the cycloalkyl group is C 3- C 6 In another embodiment, the cycloalkyl group is C 5 In another embodiment, the cycloalkyl group is C 6 Cycloalkyl, i.e., cyclohexyl. Non-limiting exemplary C 3 -C 12 Cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, norbornyl, decalin, adamantyl, cyclohexenyl and spiro[3.3]heptane.

[0165] As used herein, the term "optionally substituted cycloalkyl" by itself or as part of another group refers to cycloalkyl that is unsubstituted or substituted with one to four substituents, wherein the substituents are independently halo, nitro, cyano, hydroxy, amino (e.g., -NH 2 , alkylamino or dialkylamino), alkoxy, -SH, alkylthio, alkylcarbonyl, -C(=O)OR 8 、-OC(=O)R 8 、-C(=O)NR 8 R 9 、-NR 8 C(=O)R 9 、-SC(=O)R 8 、-SC(=O)SR 8 、--SC(=O)NR 8 R 9 、-NR 8 C(=O)SR 9 、-NR 8 C(=S)SR 9 , alkyl, haloalkyl, optionally substituted cycloalkyl, optionally substituted heterocyclyl, optionally substituted aryl or optionally substituted heteroaryl, wherein:

[0166] R 8 is hydrogen or C 1 -C 9 Alkyl, and

[0167] R 9 is hydrogen or C 1 -C 9 alkyl.

[0168] 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., C 6 -C 14Aryl. Non-limiting exemplary aryl groups include phenyl (abbreviated as "Ph"), naphthyl, phenanthrenyl, anthracenyl, indenyl, azulenyl, biphenyl, biphenylene, and fluorenyl groups. In one embodiment, the aryl group is phenyl or naphthyl. In one embodiment, the aryl group is phenyl.

[0169] As used herein, the term "optionally substituted aryl" by itself or as part of another group refers to aryl that is unsubstituted or substituted with one to four substituents, wherein the substituents are independently halo, nitro, cyano, hydroxy, amino (e.g., -NH 2 , alkylamino or dialkylamino), alkoxy, -SH, alkylthio, alkylcarbonyl, -C(=O)OR 8 、-OC(=O)R 8 、-C(=O)NR 8 R 9 、-NR 8 C(=O)R 9 、-SC(=O)R 8 、-SC(=O)SR 8 、--SC(=O)NR 8 R 9 、-NR 8 C(=O)SR 9 、-NR 8 C(=S)SR 9 , alkyl, haloalkyl, optionally substituted cycloalkyl, optionally substituted heterocyclyl, optionally substituted aryl or optionally substituted heteroaryl, wherein R 8 and R 9 As defined for the term "optionally substituted cycloalkyl".

[0170] 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, hydroxyl, amino, (e.g., -NH 2 , alkylamino or dialkylamino), alkoxy, -SH, alkylthio, alkylcarbonyl, -C(=O)OR 8 、-OC(=O)R 8 、-C(=O)NR 8 R 9 、-NR 8 C(=O)R 9 、-SC(=O)R 8 、-SC(=O)SR 8 、-SC(=O)NR 8 R 9 、-NR 8 C(=O)SR9 、--NR 8 C(=S)SR 9 , alkyl, haloalkyl, optionally substituted cycloalkyl, optionally substituted heterocyclyl, optionally substituted aryl or optionally substituted heteroaryl, wherein R 8 and R 9 As defined for the term "optionally substituted cycloalkyl".

[0171] As used herein, the term "heterocyclyl" or "heterocycle" by itself or as part of another group refers to saturated and partially unsaturated (e.g., containing one or two double bonds) monocyclic, bicyclic or tricyclic groups containing three to eighteen ring members, i.e., 3 to 18-membered heterocyclyls, which contain 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 heterocyclyl includes one or more -CH 2 -groups replaced by one or more -C(=O)-groups include cyclic urea groups (such as imidazolidin-2-one), cyclic amide groups (such as pyrrolidin-2-one or piperidin-2-one) and cyclic carbamate groups (such as oxazolidin-2-one). The term heterocyclyl also includes groups with fused optionally substituted aryl or optionally substituted heteroaryl groups, such as dihydroindole, dihydroindole-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 heterocyclyl group is a 6-membered ring containing one nitrogen atom. The heterocyclyl group 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.

[0172] As used herein, the term "optionally substituted heterocyclyl" by itself or as part of another group refers to a heterocyclyl group that is unsubstituted or substituted with one to four substituents, the substituents being independently halo, nitro, cyano, hydroxy, amino (e.g., -NH 2 , alkylamino or dialkylamino), alkoxy, -SH, alkylthio, alkylcarbonyl, -C(=O)OR 8 、-OC(=O)R 8 、-C(=O)NR 8 R 9 、-NR 8 C(=O)R 9 、-SC(=O)R 8 、-SC(=O)SR 8、-SC(=O)NR 8 R 9 、-NR 8 C(=O)SR 9 、-NR 8 C(=S)SR 9 , alkyl, haloalkyl, optionally substituted cycloalkyl, optionally substituted heterocyclyl, optionally substituted aryl or optionally substituted heteroaryl, wherein R 8 and R 9 As defined for the term "optionally substituted cycloalkyl".

[0173] 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 heteroaryls 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.

[0174] 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., -NH 2 , alkylamino or dialkylamino), alkoxy, -SH, alkylthio, alkylcarbonyl, -C(=O)OR 8 、-OC(=O)R 8 、-C(=O)NR 8 R 9 、-NR 8 C(=O)R 9 、-SC(=O)R 8 、-SC(=O)SR 8 、-SC(=O)NR 8 R 9 、-NR 8 C(=O)SR 9 、-NR 8 C(=S)SR 9 , alkyl, haloalkyl, optionally substituted cycloalkyl, optionally substituted heterocyclyl, optionally substituted aryl or optionally substituted heteroaryl, wherein R 8 and R 9 As defined for the term "optionally substituted cycloalkyl".

[0175] 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).

[0176] The term "chiral center" or "asymmetric carbon atom" refers to a carbon atom to which four different groups are attached.

[0177] 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.

[0178] The term "racemic" refers to a mixture of equal parts of enantiomers and the mixture is optically inactive.

[0179] 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.

[0180] 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).

[0181] 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 rotation of chiral substances, the percent enantiomeric excess is defined as ([α] obs / [α] max )*100, where [α] obs is the optical rotation of the enantiomeric mixture, 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.

[0182] In thin layer chromatography (TLC), the term R f Represents the retention factor. f 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.

[0183] Salts and solvates (eg, hydrates) of the disclosed compounds may also be used in the methods disclosed herein.

[0184] 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, naphthenate, nicotinate, 2-naphthalenesulfonate, oxalate, pamoate, pectinate, persulfate, 3-phenylpropionate, picrate, pivalate, propionate, trichloroacetate, trifluoroacetate, phosphate, glutamate, bicarbonate, p-toluenesulfonate, 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.

[0185] 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.

[0186] 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.

[0187] 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 as covering 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. The language in this specification should not be interpreted as indicating any unclaimed element as being necessary to practice the present disclosure.

[0188] 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 %).

[0189] Compositions and methods of use

[0190] In another embodiment, the present disclosure provides a composition comprising:

[0191] (i) a compound of the present disclosure; and

[0192] (ii) one or more elastomers; or

[0193] (iii) one or more fillers; or

[0194] (iv) one or more rubber chemicals; or

[0195] (v) one or more plasticizers; or

[0196] (vi) a second antidegradant; or

[0197] (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.

[0198] In some embodiments, the compositions of the present disclosure comprise from about 15 wt / wt% to about 85 wt / wt% of the compounds of the present disclosure. 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 w / w% to about 95 w / w%, 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%, from about 0.1 w / w% to about 4.5 w / w%. 1 wt / wt% to about 5 wt / wt%, about 0.1 wt / wt% to about 6 wt / wt%, about 0.1 wt / wt% to about 7 wt / wt%, about 0.1 wt / wt% to about 8 wt / wt%, about 0.1 wt / wt% to about 9 wt / wt%, about 0.1 wt / wt% to about 10 wt / wt%, about 0.5 wt / wt% to about 1 wt / wt%, about 0.5 wt / wt% to about 1.5 wt / wt%, about 0.5 wt / wt% to about 2 wt / wt%, about 0.5 wt / wt% to about 2.5 wt / wt%, about 0.5 wt / wt% to about 3 wt / wt%, about 0.5 wt / wt% to about 4 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 %, 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 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 %, about 1 wt / wt% to about 2.5 wt / wt%, about 1 wt / wt% to about 3 wt / wt%, about 1 wt / wt% to about 3.5 wt / wt%, about 1 wt / wt% to about 4 wt / wt%, about 1 wt / wt% to about 4.5 wt / wt%, about 1 wt / wt% to about 5 wt / wt%, about 1 wt / wt% to about 6 wt / wt%, about 1 wt / wt% to about 7 wt / wt%, about 1 wt / wt% to about 8 wt / wt%, about 1 wt / wt% to about 9 wt / wt%, about 1 wt / wt% to about 10 wt / wt%,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 w / w% to about 4 w / w%, 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 About 7 wt / wt%, about 3 wt / wt% to about 8 wt / wt%, about 3 wt / wt% to about 9 wt / wt%, about 3 wt / wt% to about 10 wt / wt%, about 3.5 wt / wt% to about 4 wt / wt%, about 3.5 wt / wt% to about 4.5 wt / wt%, about 3.5 wt / wt% to about 5 wt / wt%, about 3.5 wt / wt% to about 6 wt / wt%, about 3.5 wt / wt% to about 7 wt / wt%, about 3.5 wt / wt% to about 8 wt / wt%, about 3.5 wt / wt% to about 9 wt / wt%, about 3.5 wt / wt% to about 10 wt / wt%, about 4 wt / wt% to about 4.5 wt / wt%,about 4 wt / wt% to about 5 wt / wt%, about 4 wt / wt% to about 6 wt / wt%, about 4 wt / wt% to about 7 wt / wt%, about 4 wt / wt% to about 8 wt / wt%, about 4 wt / wt% to about 9 wt / wt%, about 4 wt / wt% to about 10 wt / wt%, about 4.5 wt / wt% to about 5 wt / wt%, about 4.5 wt / wt% to about 6 wt / wt%, about 4.5 wt / wt% to about 7 wt / wt%, about 4.5 wt / wt% to about 8 wt / wt%, about 4.5 wt / wt% to about 9 wt / wt%, about 4.5 wt / wt% to about 10 wt / wt%, about 5 wt / wt% to about 6 wt / wt%, about 5 wt / wt% % to about 7 wt / wt%, about 5 wt / wt% to about 8 wt / wt%, about 5 wt / wt% to about 9 wt / wt%, about 5 wt / wt% to about 10 wt / wt%, about 6 wt / wt% to about 7 wt / wt%, about 6 wt / wt% to about 8 wt / wt%, about 6 wt / wt% to about 9 wt / wt%, about 6 wt / wt% to about 10 wt / wt%, about 7 wt / wt% to about 8 wt / wt%, about 7 wt / wt% to about 9 wt / wt%, about 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 the compounds of the present disclosure.

[0199] 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.

[0200] In another embodiment, a composition of the present disclosure comprises a compound of the present disclosure and one or more elastomers.

[0201] 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 of vulcanized rubbers can lead to performance losses when 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.

[0202] 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).

[0203] 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.

[0204] 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.

[0205] 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.

[0206] 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.

[0207] 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 3phr 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 hr 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.

[0208] 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.

[0209] In some embodiments, compositions of the present disclosure include a compound of the present disclosure and one or more fillers.

[0210] As used herein, the term "filler" is a substance that strengthens the elastomeric composition or imparts other properties to the elastomeric composition, including but not limited to expanding the volume of the composition. Non-limiting examples of fillers include carbon black, silica, kaolin, calcium silicate, talc, carbon nanotubes (CNT), carbon fiber (HCF), graphite, graphene, aluminosilicates, starch and fibers, and combinations thereof.

[0211] In some embodiments, the filler is derived from a natural source. For example, the silica may be derived from rice husks.

[0212] 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 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 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.

[0213] 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.

[0214] 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.

[0215] 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.

[0216] 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, "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.

[0217] 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.

[0218] As used herein, the term "vulcanizing agent" refers to any substance that can crosslink between elastomers. Vulcanizing agents can achieve crosslinking between separate polymer chains of elastomers by various mechanisms, including but not limited to by forming covalent bonds between the vulcanizing agent and two or more separate polymer chains, or by generating free radical substances on separate polymer chains that can combine to form covalent bonds between two polymer chains. Non-limiting examples of vulcanizing agents include sulfur, peroxides, sulfurized vegetable oils, ointments and resins. Non-limiting examples of sulfur include octasulfur (S 8 ), cyclododecyl sulfide (S 12 ) and polymeric sulfur. Non-limiting examples of peroxides include benzoyl peroxide, dicumyl peroxide (DC), 2,5-dimethyl-2,5-di-(tert-butylperoxy)-3-hexyne (2,5Tri), 2,5-dimethyl-2,5-di-(tert-butylperoxy) hexane (DDPH), di-(2-tert-butylperoxyisopropyl) benzene (VC), butyl-4,4-di-(tert-butylperoxy) valerate (VAL) and 1,1-di-(tert-butylperoxy)-3,3,5-trimethylcyclohexane (TMC). Non-limiting examples of resins include 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.

[0219] As used herein, the term "accelerator" refers to any material that increases the kinetics of vulcanization. In some embodiments, accelerators enable vulcanization to be carried out at relatively low temperatures and / or more effectively utilize vulcanizing agents (such as sulfur). The limiting examples of accelerators include guanidine, thiazole, sulfenamide, sulfenimide, 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) or its combination. 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).

[0220] 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 act 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.

[0221] 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.

[0222] 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.

[0223] 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%.

[0224] 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.

[0225] 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.

[0226] 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.

[0227] 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.

[0228] 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.

[0229] 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. , about 5 phr to about 40 phr, about 10 phr to about 15 phr, about 10 phr to about 20 phr, about 10 phr to about 25 phr, about 10 phr to about 30 phr, about 10 phr to about 35 phr, about 10 phr to about 40 phr, about 15 phr to about 20 phr, about 15 phr to about 25 phr, about 15 phr to about 30 phr, about 15 phr to about 35 phr, about 15 phr to about 40 phr, about 15 phr to about 20 phr, about 15 phr to about 25 phr, about 15 phr to about 30 phr, about 15 phr to about 35 phr, about 15 phr to about The invention also provides one or more plasticizers from about 20 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.

[0230] 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.

[0231] 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.

[0232] 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.

[0233] 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.

[0234] 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.

[0235] 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.

[0236] 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.

[0237] 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.

[0238] 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.

[0239] 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.

[0240] 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).

[0241] 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.

[0242] 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.

[0243] Vulcanized elastomer products

[0244] 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.

[0245] The present disclosure also provides vulcanized elastomeric articles comprising the compositions described herein.

[0246] The present disclosure also provides vulcanized elastomeric articles prepared using the compounds of the present disclosure.

[0247] The present disclosure also provides vulcanized elastomeric articles prepared using the compositions described herein.

[0248] 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.

[0249] 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.

[0250] 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.

[0251] method

[0252] The present disclosure also provides a method for preparing a vulcanized elastomeric article, the method comprising:

[0253] (a) forming a composition as described herein into a shaped shape; and

[0254] (b) vulcanizing the formed shape,

[0255] To provide a vulcanized elastomeric product.

[0256] In some embodiments, vulcanization is performed at an average temperature of about 140° C. to about 160° C. In some embodiments, vulcanization is performed at an average temperature of about 80° C. to about 100° C., about 80° C. to about 120° C., about 80° C. to about 140° C., about 80° C. to about 160° C., about 80° C. to about 180° C., about 80° C. to about 200° C., about 100° C. to about 120° C., about 100° C. to about 140° C., about 100° C. to about 160° C., about 100° C. to about 180° C., about 100° C. to about 200° C., about 120° C. to about 140° C., about 120° C. to about 160° C., about 120° C. to about 180° C., about 120° C. to about 200° C., about 140° C. to about 180° C., about 140° C. to about 200° C., about 160° C. to about 180° C., about 160° C. to about 200° C., or about 180° C. to about 200° C.

[0257] 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.

[0258] The present disclosure also provides a method for retreading a tire, the method comprising:

[0259] (a) applying a composition as described herein to a tire;

[0260] (b) providing a pre-cured tread around the tire;

[0261] (c) providing a curing envelope around the tire; and

[0262] (d) vulcanizing the tire.

[0263] Reagent test kit

[0264] 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.

[0265] Example

[0266] Example 1

[0267] Synthesis of N-(sec-butyl)-1H-indol-5-amine (Compound 1)

[0268]

[0269] 5-Aminoindole (20.08 g; 151.9 mmol), isopropanol (117 mL) and methyl ethyl ketone (47.7 mL; 532 mmol) were added to a 500 mL round bottom flask equipped with a stirring bar, alcohol thermometer and reflux condenser. The reaction mixture was heated under N 2 Stir and heat under protection (oil bath temperature is set to 90°C). Once reflux temperature is reached (internal temperature = about 80°C), the temperature is maintained for 7.5 hours to form the imine intermediate. After cooling to room temperature overnight, the flask is immersed in a cold tap water bath. Sodium triacetoxyborohydride (42.5g; 201mmol) (peak temperature = 31°C) is added in batches over 10 minutes. Once the addition of sodium triacetoxyborohydride is complete, the sides of the funnel are rinsed with isopropanol (5mL). The reaction mixture is stirred for 7 minutes and then the cooling bath is removed. The reaction mixture is stirred for about 2.5 hours without additional cooling or heating. The flask is cooled with a cold tap water bath. Under vigorous stirring, 2M NaOH aqueous solution (102mL) is added in batches over 8-9 minutes. Ethyl acetate (70mL) is added (no exotherm is observed). The two-phase system is transferred to a separatory funnel. The flask is rinsed with additional ethyl acetate (180mL) and added to the separatory funnel together with another portion of 2M NaOH aqueous solution (102mL). Shake the separatory funnel and allow the sediment to settle. Discard the aqueous phase. Wash the organic phase with 2M NaOH aqueous solution (102 mL), deionized water (102 mL), and saturated NaCl aqueous solution (102 mL). The organic solution is washed with anhydrous MgSO 4 Dry, filter and remove the volatiles under reduced pressure (rotavapor; water bath = 55°C). The dark liquid obtained is dried on a rotary evaporator (60°C; <2 mbar) for 1.5 hours to give 27.2 g (95% of theory with respect to 5-aminoindole) of N-(sec-butyl)-1H-indol-5-amine (Compound 1) as a dark oil. Compound 1 is separated by evaporation at 4 °C for 1 h. 1 H and 13 C nuclear magnetic resonance (NMR) spectroscopy characterization, respectively. Figure 1 and 2 As shown, and its purity was >93.5% by LC-MS / UV.

[0270] Example 2

[0271] Synthesis of N-(sec-butyl)indoline-5-amine (Compound 2)

[0272]

[0273] Compound 1 (1.03 g; 5.47 mmol) was added to a 100 mL round bottom flask equipped with a stirring bar. The flask was heated with N 2 The flask was stirred with a layer of trifluoroacetic acid (5.7 mL). After about 18-24 hours, the flask was cooled with a cold tap water bath. Triethylsilane (1.8 mL; 11.3 mmol) was added via syringe. No exotherm was observed. The resulting two-phase system was stirred at room temperature for about 22 hours. Silica gel TLC (50% ethyl acetate in hexanes / hexanes) showed that R f = 0.7, the starting material completely disappears, and at R f =0.2 formed a strong point. Cool the flask with a cold tap water bath. 2mol / L NaOH aqueous solution (43mL) was slowly added to the flask. Ethyl acetate (26mL) was added, and the two-phase system was stirred vigorously until the oily substance was completely dissolved. The aqueous layer was discarded. The organic layer was washed with deionized water (20mL) and brine (20mL), and then its volatiles were removed under reduced pressure (rotary evaporator; water bath = 50°C). The crude material (black liquid; about 1.37g) was diluted with 50% ethyl acetate (3.0mL) in hexane. The resulting solution was loaded into a chromatographic column with an inner diameter of 1 inch prepared in advance with silica gel 60 (about 7.5 inches high) and 50% ethyl acetate in hexane. The column was eluted with 50% ethyl acetate in hexane and then with 100% ethyl acetate. Each part was analyzed by silica gel TLC (50% ethyl acetate in hexane). Collect the R f = 0.2 fractions were combined and isolated in yield = 0.492 g as a dark purple oil (47% based on compound 1). Compound 2 was 1 H and 13 C NMR characterization, respectively. Figure 4 and 5 As shown, the purity was determined by LC-MS to be 96.68%.

[0274] Compound 2 can also be synthesized by reductive alkylation of 5-nitroindoline as follows:

[0275]

[0276] A 300 mL Paar autoclave was charged with 5-nitroindoline (5.0 g; 30.46 mmol), isopropanol (150 mL), methyl ethyl ketone (4.5 mL; 50.2 mmol) and 3% platinum sulfide on carbon (0.1 g). The reaction mixture was heated under pressurized H 2 The mixture was heated to 120°C (250 PSI) for 3 hours. LC-UV / MS of the crude mixture indicated the presence of several compounds including the desired product Compound 2.

[0277] Example 3

[0278] Synthesis of N-(1-phenylethyl)-1H-indol-5-amine (Compound 19)

[0279]

[0280] A 100 mL round-bottom flask equipped with a stirring bar and a reflux condenser was charged with 5-aminoindole (2.425 g; 18.35 mmol) and isopropanol (11 mL). 2 The reaction mixture was stirred at room temperature for 1 hour, refluxed for 3 hours (oil bath = 91 °C), and then allowed to cool to room temperature overnight. Silica gel TCL (20% ethyl acetate in hexanes) indicated a peak at R f =0.35, a spot is formed. f =0.15 (5-aminoindole) and 0.60 (acetophenone) spots are still quite intense. The reaction mixture is refluxed for another period of time (6-6.5 hours), and then the flask is cooled with a cold tap water bath. Sodium triacetoxyborohydride (4.67 g; 22.0 mmol) is added in batches over 10-11 minutes. The cooling bath is removed. The reaction mixture is stirred at room temperature overnight (about 16 hours). 1 mol / L NaOH aqueous solution (68 mL) is added to the flask in batches. The mixture is mixed with ethyl acetate (50 mL) in a separatory funnel. After shaking and decanting, the aqueous phase is discarded. The organic phase is washed with 1 mol / L NaOH aqueous solution (25 mL), dilute NaCl aqueous solution (50 mL), saturated NaCl aqueous solution (25 mL), dried over anhydrous MgSO4, filtered, and finally the volatiles are removed under reduced pressure (rotary evaporator; water bath = 50 ° C). The resulting dark oil (4.29 g) is dissolved in toluene (5.5 mL). The resulting solution was loaded onto a 41 mm inner diameter chromatographic column (22-23 cm silica gel height) prepared in advance with silica gel 60 and 20% ethyl acetate eluent in hexane. The column was eluted with eluent. The resulting fractions (about 30 mL each) were analyzed by silica gel TLC (20% ethyl acetate in hexane). The fractions containing the desired product (R f=0.35), combined and stripped of volatiles under reduced pressure (rotavapor; water bath r = 55 ° C). Further drying on a rotary evaporator (water bath = 55 ° C; 1-6 mbar; 15 minutes) gave 2.33 g of a clear light yellow oil, which darkened upon standing under ambient conditions (proton NMR showed the presence of residual AcOEt). The flask containing the material was immersed in a sand bath. Drying in a vacuum oven at 70 ° C for several hours and then at room temperature overnight gave compound 19 as a light blue viscous material (2.1 g; 48% isolated yield relative to 5-aminoindole). Compound 19 was purified by 1 H and 13 C NMR characterization, respectively. Figure 6 and 7 The purity of the product was 93.7% as determined by LC-MS.

[0281] Example 4

[0282] Use of Compound 1 in sidewall preparations

[0283] Compound 1 was used as an antidegradant in the sidewall formulation to prepare a rubber compound (Example #1). As shown in Table 1, the rubber compound was a 50 / 50 blend of natural rubber and butadiene rubber with N500 series carbon black. The vulcanization properties of the compound were characterized by a moving die rheometer and are summarized in Table 2.

[0284] Table 1

[0285]

[0286]

[0287] Table 2

[0288] Example #1 Temperature(℃) 150 ML(dNm) 2.58 MH(dNm) 15 Ts2(min) 5.94 T10(min) 5.6 T50(min) 7.64 T90(min) 12.09

[0289] Example 5

[0290] Anti-ozone performance of compound 1 in sidewall formulations

[0291] The rubber compound (Example #1) prepared in Example 2 was cured at 150°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, and 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 under three different conditions: static, intermittent and dynamic in the ozone chamber. The ozone test sample was maintained at 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. Intermittent testing alternated between 18 minutes of dynamic exposure and 102 minutes of static 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.

[0292] The ozone resistance of antidegradant formulated compounds was evaluated by the force retention percentage. The force retention percentage is defined by Equation 1:

[0293] Formula 1:

[0294] where F 0 F is the force at 100% strain before ozone testing, and F is the force at 100% strain after the sample has been aged in an ozone chamber for 16 hours under static, intermittent or dynamic exposure. A higher percentage of force retention indicates better ozone resistance of the anti-degradation compound incorporated in the vulcanized rubber compound.

[0295] exist Figure 3(a)-3(c) The percent force retention results for static, intermittent, and dynamic conditions are plotted as a function of ozone aging time.

[0296] Example 6

[0297] Oxidation Induction Time (OIT) Performance of the Disclosed Compounds

[0298] In order to demonstrate the antioxidant efficacy of the compounds disclosed herein, the oxidation induction time (OIT) of representative compounds was evaluated. OIT is measured according to a procedure performed in a differential scanning calorimeter (DSC) and is used to predict the thermal oxidation performance of a 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 onset of an increase in heat flow) is measured.

[0299] 0.5 wt % of the disclosed compound or no antidegradant (blank) was mixed with polyisoprene and 2The OIT test was performed at a constant temperature of 150°C or 160°C. Table 3 shows the peak time (minutes) of the OIT test. As shown in the data in Table 3, the compounds of the present disclosure exhibit antioxidant properties compared to the blank control, indicating that they are useful in rubber and other applications that can benefit from active antioxidants.

[0300] Table 3

[0301]

[0302]

[0303] 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 composition comprising: (i) a compound having the formula (I): or a salt or solvate thereof, wherein: is a single bond or a double bond; R 1 Selected from the group consisting of: C1-C 12 Alkyl, -CHR 1a R 1b , optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl; R 1a is selected from the group consisting of optionally substituted phenyl, optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 6-membered heterocyclyl, and optionally substituted 5- or 6-membered heteroaryl; R 1b Selected from the group consisting of hydrogen and C1-C9 alkyl; R 2a , R 2b and R 2c independently selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, -OH, C1-C8 alkoxy, -SH, C1-C8 alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5 or 6 membered heteroaryl; or R 2a and R 2b Together with the two carbon atoms to which they are attached, they form an optionally substituted C3-C6 cycloalkyl, an optionally substituted 4 to 6-membered heterocyclyl, an optionally substituted 4 to 6-membered aryl, or an optionally substituted 4 to 6-membered heteroaryl; and R 2c Selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, -OH, C1-C8 alkoxy, -SH, C1-C8 alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl; R 3a Selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, -OH, C1-C8 alkoxy, -SH, C1-C8 alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5 or 6 membered heteroaryl; and R 3b Selected from the group consisting of: hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, -OH, C1-C8 alkoxy, -SH, C1-C8 alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, and optionally substituted 5 or 6 membered heteroaryl; or R 3a and R 3b Together with the two carbon atoms to which they are attached, they form an optionally substituted C3-C 12 Cycloalkyl or an optionally substituted 4- or 6-membered heterocyclic group; R 4 is selected from the group consisting of hydrogen and C1-C9 alkyl; and R 5 is selected from the group consisting of hydrogen and C1-C9 alkyl; 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.

2. The composition of claim 1, wherein It's a double bond.

3. The composition of claim 1, wherein It is a single bond.

4. The composition of any one of claims 1 to 3, wherein R 1 Choose from C1-C 12 The group consisting of an alkyl group and an optionally substituted phenyl group.

5. The composition of any one of claims 1 to 4, wherein R 1 It is phenyl.

6. The composition of any one of claims 1 to 4, wherein R 1 Selected from the group consisting of methyl, ethyl, propyl, isopropyl, tert-butyl, sec-butyl, isobutyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl.

7. The composition of claim 6, wherein R 1 It is sec-butyl.

8. The composition of claim 6, wherein R 1 It is isopropyl.

9. The composition of any one of claims 1 to 3, wherein: R 1 Yes - CHR 1a R 1b ; R 1a Selected from the group consisting of: Q is selected from the group consisting of -NH-, -O-, and -S-; and R 1b is selected from the group consisting of hydrogen and methyl.

10. The composition of any one of claims 1 to 9, wherein R 2a , R 2b and R 2c For hydrogen.

11. The composition of any one of claims 1 to 10, wherein R 3a and R 3b For hydrogen.

12. The compound of claim 1, wherein the compound is selected from any one or more of the compounds in Table 1.

13. The composition of any one of claims 1-12, wherein the composition comprises one or more elastomers.

14. The composition of claim 13, 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.

15. The composition of claim 13 or 14, wherein the one or more elastomers comprises natural rubber (NR).

16. The composition of claim 15, wherein the one or more elastomers comprises from about 5 wt / wt% to about 80 wt / wt% natural rubber (NR).

17. A composition as claimed in claim 15 or 16, wherein the natural rubber comprises rubber derived from an alternative rubber plant.

18. The composition of claim 17, wherein the alternative rubber plant is Guayule (Guayule) or Rubber Grass (Russian Taraxacum).

19. The composition of any one of claims 13-18, wherein the one or more elastomers comprises a synthetic rubber.

20. The composition of claim 19, 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.

21. The composition of claim 20, wherein the unsaturated rubber comprises polyisoprene rubber (IR), butyl rubber (IIR), polybutadiene rubber (BR), styrene butadiene rubber (SBR), nitrile rubber (NBR), chloroprene rubber (CR), ethylene propylene diene rubber (EPDM), or a blend thereof.

22. The composition of claim 21, wherein the unsaturated rubber comprises styrene butadiene rubber (SBR).

23. The composition of claim 22, wherein the one or more elastomers comprises from about 5 wt / wt% to about 80 wt / wt% styrene butadiene rubber (SBR).

24. The composition of any one of claims 21-23, wherein the unsaturated rubber comprises polybutadiene rubber (BR).

25. The composition of claim 24, wherein the one or more elastomers comprises from about 5 wt / wt% to about 80 wt / wt% polybutadiene rubber (BR).

26. The composition of any one of claims 21-25, wherein the unsaturated rubber comprises butyl rubber (IIR).

27. The composition of claim 26, wherein the one or more elastomers comprises about 1 wt / wt% to about 30 wt / wt% butyl rubber (IIR).

28. The composition of any one of claims 20-27, 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.

29. The composition of any one of claims 13-28, wherein the one or more elastomers further comprises reclaimed rubber.

30. The composition of any one of claims 1-29, wherein the composition comprises from about 0.1 phr to about 10 phr of the compound.

31. The composition of claim 30, wherein the composition comprises from about 0.5 phr to about 5 phr of the compound.

32. The compound of claim 31, wherein the composition comprises from about 1 phr to about 5 phr of the compound.

33. The composition of any one of claims 1-32, wherein the composition comprises one or more fillers.

34. The composition of claim 33, 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.

35. The composition of claim 33 or 34, wherein the composition comprises from about 30 phr to about 500 phr of one or more fillers.

36. The composition of any one of claims 33-35, 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.

37. The composition of claim 36, wherein the one or more fillers comprises silica.

38. The composition of claim 37, wherein the silicon dioxide is derived from rice husks.

39. The composition of any one of claims 33-38, wherein the one or more fillers comprises carbon black.

40. The composition of any one of claims 1-39, wherein the composition comprises one or more rubber chemicals.

41. The composition of claim 40, 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.

42. The composition of claim 40 or 41, wherein the composition comprises from about 0.1 phr to about 30 phr of one or more rubber chemicals.

43. The composition of claim 42, wherein the composition comprises from about 1 phr to about 20 phr of one or more rubber chemicals.

44. The composition of any one of claims 40-43, 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.

45. The composition of claim 44, wherein the one or more rubber chemicals include one or more vulcanizing agents.

46. ​​The composition of claim 45, wherein the one or more vulcanizing agents comprises sulfur, a peroxide, a resin, or a combination thereof.

47. The composition of claim 46, wherein the sulfur is octasulfur (S8), cyclododecylsulfur (S 12 ), polymeric sulfur or a combination thereof.

48. The composition of claim 46, 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.

49. The composition of claim 46, wherein the resin is a binding resin.

50. The composition of claims 44-49, wherein the one or more rubber chemicals include one or more accelerators.

51. The composition of claim 50, wherein the one or more accelerators comprise guanidine, thiazole, sulfenamide, sulfenimide, thiuram, dithiocarbamate, xanthate, thiophosphate, or a combination thereof.

52. The composition of claim 51, wherein the guanidine is diphenylguanidine (DPG).

53. The composition of claim 51, 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.

54. The composition of claim 51, 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.

55. The composition of claim 51, 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.

56. The composition of claim 51, 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.

57. The composition of any one of claims 44-56, wherein the one or more rubber chemicals include one or more activators.

58. The composition of claim 57, wherein the one or more activators comprise a metal oxide, an acid, a metal complex, or a combination thereof.

59. The composition of claim 58, wherein the metal oxide comprises zinc oxide, magnesium oxide, lead oxide, or a combination thereof.

60. The composition of claim 58, wherein the acid comprises stearic acid, lauric acid, or a combination thereof.

61. The composition of claim 58, wherein the metal complex comprises zinc ethylhexanoate.

62. The composition of any one of claims 44-61, wherein the one or more rubber chemicals include one or more pre-vulcanization inhibitors.

63. The composition of claim 62, wherein the one or more pre-cure inhibitors include N-(cyclohexylthio)phthalimide (CTP), benzoic anhydride, salicylic anhydride, phthalic anhydride, or a combination thereof.

64. A composition as described in any one of claims 1-63, wherein the composition comprises one or more plasticizers.

65. The composition of claim 64, 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 plasticizers.

66. The composition of claim 64 or 65, wherein the composition comprises from about 0.1 phr to about 30 phr of one or more plasticizers.

67. The composition of claim 66, wherein the composition comprises from about 1 phr to about 20 phr of one or more plasticizers.

68. The composition of any one of claims 64-67, wherein the one or more plasticizers comprise mineral oils, organic esters, resins, waxes, ester plasticizers, oils of natural origin, or combinations thereof.

69. The composition of claim 68, wherein the mineral oil is a naphthenic oil, a paraffinic oil or a aromatic oil.

70. The composition of claim 68, wherein the oil of natural origin is soybean oil, vegetable oil or orange oil.

71. The composition of any one of claims 1-70, wherein the composition further comprises a second antidegradant.

72. The composition of claim 71, wherein the composition comprises about 15% to about 85% w / w of the compound and about 15% to about 85% w / w of the second antidegradant.

73. The composition of claim 71 or 72, wherein the second antidegradant is present in an amount of about 0.001 phr to about 10 phr.

74. The composition of claim 73, wherein the second antidegradant is present in an amount of about 0.1 phr to about 5 phr.

75. The composition of claim 74, wherein the second antidegradant is present in an amount of about 0.5 phr to about 5 phr.

76. The composition of claim 75, wherein the second antidegradant is present in an amount of about 1 phr to about 5 phr.

77. The composition of any one of claims 71-76, wherein the second antidegradant is an antioxidant.

78. The composition of any one of claims 71-76, wherein the second antidegradant is an antiozonant.

79. The composition of any one of claims 71-78, wherein the second antidegradant is p-phenylenediamine (PPD), trimethyldihydroquinoline (TMQ), phenols, alkylated diphenylamine (DPA) or diphenylamine-ketone condensates.

80. The composition of claim 79, 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).

81. The composition of claim 80, wherein the PPD is 6PPD.

82. The composition of claim 79, wherein the TMQ is 2,2,4-trimethyl-1,2-dihydroquinoline or an oligomer or polymer thereof.

83. A composition comprising a compound of formula (I): or a salt or solvate thereof, wherein: is a single bond or a double bond; R 1 Selected from the group consisting of: C1-C 12 Alkyl, -CHR 1a R 1b , optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl; R 1a is selected from the group consisting of optionally substituted phenyl, optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 6-membered heterocyclyl, and optionally substituted 5- or 6-membered heteroaryl; R 1b Selected from the group consisting of hydrogen and C1-C9 alkyl; R 2a , R 2b and R 2c independently selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, -OH, C1-C8 alkoxy, -SH, C1-C8 alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5 or 6 membered heteroaryl; or R 2a and R 2b Together with the two carbon atoms to which they are attached, they form an optionally substituted C3-C6 cycloalkyl, an optionally substituted 4 to 6-membered heterocyclyl, an optionally substituted 4 to 6-membered aryl, or an optionally substituted 4 to 6-membered heteroaryl; and R 3c Selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, -OH, C1-C8 alkoxy, -SH, C1-C8 alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5 or 6 membered heteroaryl; R 3a Selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, -OH, C1-C8 alkoxy, -SH, C1-C8 alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5 or 6 membered heteroaryl; and R 3b Selected from the group consisting of: hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, -OH, C1-C8 alkoxy, -SH, C1-C8 alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, and optionally substituted 5 or 6 membered heteroaryl; or R 3a and R 3b Together with the two carbon atoms to which they are attached, they form an optionally substituted C3-C 12 cycloalkyl or an optionally substituted 4- to 6-membered heterocyclic group; R 4 is selected from the group consisting of hydrogen and C1-C9 alkyl; and R 5 selected from the group consisting of hydrogen and C1-C9 alkyl; and one or more carriers.

84. The composition of claim 83, wherein It's a double bond.

85. The composition of claim 83, wherein It is a single bond.

86. The composition of any one of claims 83-85, wherein R 1 Choose from C1-C 12 The group consisting of an alkyl group and an optionally substituted phenyl group.

87. The composition of any one of claims 83-86, wherein R 1 It is phenyl.

88. The composition of any one of claims 83-86, wherein R 1 Selected from the group consisting of methyl, ethyl, propyl, isopropyl, tert-butyl, sec-butyl, isobutyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl.

89. The composition of claim 88, wherein R 1 It is sec-butyl.

90. The composition of claim 88, wherein R 1 It is isopropyl.

91. The composition of any one of claims 83-85, wherein: R 1 Yes - CHR 1a R 1b ; R 1a Selected from the group consisting of: Q is selected from the group consisting of -NH-, -O-, and -S-; and R 1b is selected from the group consisting of hydrogen and methyl.

92. The composition of any one of claims 83-91, wherein R 2a , R 2b and R 2c For hydrogen.

93. The composition of any one of claims 83-94, wherein R 3a and R 3b For hydrogen.

94. The composition of claim 83, wherein the compound is selected from any one or more of the compounds of Table 1.

95. A method for preparing the composition of any one of claims 83-94, comprising mixing the compound with the one or more carriers.

96. A vulcanized elastomeric article comprising a compound having formula (I): or a salt or solvate thereof, wherein: is a single bond or a double bond; R 1 Selected from the group consisting of: C1-C 12 Alkyl, -CHR 1a R 1b , optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl; R 1a is selected from the group consisting of optionally substituted phenyl, optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 6-membered heterocyclyl, and optionally substituted 5- or 6-membered heteroaryl; R 1b Selected from the group consisting of hydrogen and C1-C9 alkyl; R 2a , R 2b and R 2c independently selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, -OH, C1-C8 alkoxy, -SH, C1-C8 alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5 or 6 membered heteroaryl; or R 2a and R 2b Together with the two carbon atoms to which they are attached, they form an optionally substituted C3-C6 cycloalkyl, an optionally substituted 4 to 6-membered heterocyclyl, an optionally substituted 4 to 6-membered aryl, or an optionally substituted 4 to 6-membered heteroaryl; and R 3c Selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, -OH, C1-C8 alkoxy, -SH, C1-C8 alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5 or 6 membered heteroaryl; R 3a Selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, -OH, C1-C8 alkoxy, -SH, C1-C8 alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5 or 6 membered heteroaryl; and R 3b Selected from the group consisting of: hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, -OH, C1-C8 alkoxy, -SH, C1-C8 alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, and optionally substituted 5 or 6 membered heteroaryl; or R 3a and R 3b Together with the two carbon atoms to which they are attached, they form an optionally substituted C3-C 12 cycloalkyl or an optionally substituted 4- to 6-membered heterocyclic group; R 4 is selected from the group consisting of hydrogen and C1-C9 alkyl; and R 5 selected from the group consisting of hydrogen and C1-C9 alkyl; and one or more carriers.

97. The article of claim 96, wherein It's a double bond.

98. The article of claim 96, wherein It is a single bond.

99. The article of claim 96-98, wherein R 1 Choose from C1-C 12 The group consisting of an alkyl group and an optionally substituted phenyl group.

100. The article of claim 96-98, wherein R 1 It is phenyl.

101. The article of any one of claims 96-98, wherein R 1 Selected from the group consisting of methyl, ethyl, propyl, isopropyl, tert-butyl, sec-butyl, isobutyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl.

102. The article of claim 101, wherein R 1 It is sec-butyl.

103. The article of claim 101, wherein R 1 It is isopropyl.

104. The article of any one of claims 96-98, wherein: R 1 Yes - CHR 1a R 1b ; R 1a Selected from the group consisting of: Q is selected from the group consisting of -NH-, -O-, and -S-; and R 1b is selected from the group consisting of hydrogen and methyl.

105. The article of any one of claims 96-104, wherein R 2a , R 2b and R 2c For hydrogen.

106. The article of any one of claims 96-104, wherein R 3a and R 3b For hydrogen.

107. The article of claim 96, wherein the compound is selected from any one or more of the compounds of Table 1.

108. A vulcanized elastomeric article comprising the composition of any one of Claims 1-94.

109. A vulcanized elastomeric article prepared using the composition of any one of claims 1-94.

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

111. The vulcanized elastomeric article of claim 110, 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.

112. The vulcanized elastomeric article of claim 109 or 109, wherein the vulcanized elastomeric article is a component of a tire.

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

114. The vulcanized elastomeric article of claim 108 or 109, 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.

115. A method for preparing a vulcanized elastomeric article, the method comprising: (a) forming the composition of any one of claims 13 to 82 into a shaped shape; and (b) Vulcanizing the formed shape To provide a vulcanized elastomeric product.

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

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

118. The method of any one of claims 115-117, wherein the vulcanized elastomeric article is a tire.

119. The method of claim 118, 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.

120. The method of any one of claims 115-117, wherein the vulcanized elastomeric article is a component of a tire.

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

122. The method of any one of claims 115-121, 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.

123. A lubricant composition comprising a lubricant and a compound having formula (I): or a salt or solvate thereof, wherein: is a single bond or a double bond; R 1 Selected from the group consisting of: C1-C 12 Alkyl, -CHR 1a R 1b , optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl; R 1a is selected from the group consisting of optionally substituted phenyl, optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 6-membered heterocyclyl, and optionally substituted 5- or 6-membered heteroaryl; R 1b Selected from the group consisting of hydrogen and C1-C9 alkyl; R 2a , R 2b and R 2c independently selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, -OH, C1-C8 alkoxy, -SH, C1-C8 alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5 or 6 membered heteroaryl; or R 2a and R 2b Together with the two carbon atoms to which they are attached, they form an optionally substituted C3-C6 cycloalkyl, an optionally substituted 4 to 6-membered heterocyclyl, an optionally substituted 4 to 6-membered aryl, or an optionally substituted 4 to 6-membered heteroaryl; and R 3c Selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, -OH, C1-C8 alkoxy, -SH, C1-C8 alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5 or 6 membered heteroaryl; R 3a Selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, -OH, C1-C8 alkoxy, -SH, C1-C8 alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5 or 6 membered heteroaryl; and R 3b Selected from the group consisting of: hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, -OH, C1-C8 alkoxy, -SH, C1-C8 alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, and optionally substituted 5 or 6 membered heteroaryl; or R 3a and R 3b Together with the two carbon atoms to which they are attached, they form an optionally substituted C3-C 12 cycloalkyl or an optionally substituted 4- to 6-membered heterocyclic group; R 4 is selected from the group consisting of hydrogen and C1-C9 alkyl; and R 5 Selected from the group consisting of hydrogen and C1-C9 alkyl.

124. A combustible fuel composition comprising a combustible fuel and a compound of formula (I): or a salt or solvate thereof, wherein: is a single bond or a double bond; R 1 Selected from the group consisting of: C1-C 12 Alkyl, -CHR 1a R 1b , optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl; R 1a is selected from the group consisting of optionally substituted phenyl, optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 6-membered heterocyclyl, and optionally substituted 5- or 6-membered heteroaryl; R 1b Selected from the group consisting of hydrogen and C1-C9 alkyl; R 2a , R 2b and R 2c independently selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, -OH, C1-C8 alkoxy, -SH, C1-C8 alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5 or 6 membered heteroaryl; or R 2a and R 2b Together with the two carbon atoms to which they are attached, they form an optionally substituted C3-C6 cycloalkyl, an optionally substituted 4 to 6-membered heterocyclyl, an optionally substituted 4 to 6-membered aryl, or an optionally substituted 4 to 6-membered heteroaryl; and R 3c Selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, -OH, C1-C8 alkoxy, -SH, C1-C8 alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5 or 6 membered heteroaryl; R 3a Selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, -OH, C1-C8 alkoxy, -SH, C1-C8 alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5 or 6 membered heteroaryl; and R 3b Selected from the group consisting of: hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, -OH, C1-C8 alkoxy, -SH, C1-C8 alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, and optionally substituted 5 or 6 membered heteroaryl; or R 3a and R 3b Together with the two carbon atoms to which they are attached, they form an optionally substituted C3-C 12 cycloalkyl or an optionally substituted 4- to 6-membered heterocyclic group; R 4 is selected from the group consisting of hydrogen and C1-C9 alkyl; and R 5 Selected from the group consisting of hydrogen and C1-C9 alkyl.

125. A fuel additive composition comprising a fuel additive and a compound having formula (I): or a salt or solvate thereof, wherein: is a single bond or a double bond; R 1 Selected from the group consisting of: C1-C 12 Alkyl, -CHR 1a R 1b , optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl; R 1a is selected from the group consisting of optionally substituted phenyl, optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 6-membered heterocyclyl, and optionally substituted 5- or 6-membered heteroaryl; R 1b Selected from the group consisting of hydrogen and C1-C9 alkyl; R 2a , R 2b and R 2c independently selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, -OH, C1-C8 alkoxy, -SH, C1-C8 alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , 4 to 6 membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5 or 6 membered heteroaryl; or R 2a and R 2b Together with the two carbon atoms to which they are attached, they form an optionally substituted C3-C6 cycloalkyl, an optionally substituted 4 to 6-membered heterocyclyl, an optionally substituted 4 to 6-membered aryl, or an optionally substituted 4 to 6-membered heteroaryl; and R 3c Selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, -OH, C1-C8 alkoxy, -SH, C1-C8 alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5 or 6 membered heteroaryl; R 3a Selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, optionally substituted C3-C8 cycloalkyl, -OH, C1-C8 alkoxy, -SH, C1-C8 alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5 or 6 membered heteroaryl; and R 3b Selected from the group consisting of: hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, -OH, C1-C8 alkoxy, -SH, C1-C8 alkylthio, -C(=O)OR 4 、-OC(=O)R 4 、-C(=O)NR 4 R 5 、-NR 4 C(=O)R 5 、-NR 4 R 5 、-SC(=O)R 4 、-SC(=O)SR 4 、-SC(=O)NR 4 R 5 、-NR 4 C(=O)SR 5 、-NR 4 C(=S)SR 5 , optionally substituted 4 to 6 membered heterocyclyl, and optionally substituted 5 or 6 membered heteroaryl; or R 3a and R 3b Together with the two carbon atoms to which they are attached, they form an optionally substituted C3-C 12 cycloalkyl or an optionally substituted 4- to 6-membered heterocyclic group; R 4 is selected from the group consisting of hydrogen and C1-C9 alkyl; and R 5 Selected from the group consisting of hydrogen and C1-C9 alkyl.

126. A method for retreading a tire, the method comprising: (a) applying the composition of any one of claims 13 to 82 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.

127. A kit comprising the composition of any one of claims 1-94 and instructions for using the composition in a vulcanizable elastomeric composition.

128. A kit comprising the composition of any one of claims 1-94 and instructions for using the composition to prepare a vulcanized elastomeric article.

129. The composition of any one of claims 1-12, wherein the composition comprises from about 0.1% w / w to about 10% w / w of the compound.

130. The composition of any one of claims 83-94, wherein the composition comprises from about 0.1% w / w to about 10% w / w of the compound.

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